Abstract
C18H28N2O4P2S4Zn, triclinic, P1̄ (no. 2), a = 15.2379(1) Å, b = 17.3322(2) Å, c = 21.8829(1) Å, α = 75.919(1)°, β = 78.050(1)°, γ = 68.170(1)°, V = 5159.97(8) Å3, Z = 8, Rgt(F) = 0.0246, wRref(F2) = 0.0681, T = 100 K.

A part of the molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless prism |
| Size: | 0.28 × 0.17 × 0.12 mm |
| Wavelength: | Cu Kα radiation (1.54184 Å) |
| μ: | 5.76 mm−1 |
| Diffractometer, scan mode: | XtaLAB Synergy, ω |
| θmax, completeness: | 67.1°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 123255, 18426, 0.031 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 17365 |
| N(param)refined: | 1143 |
| Programs: | CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Zn1 | 1.27642(2) | 0.07163(2) | 0.07760(2) | 0.01050(5) |
| Zn2 | 0.72088(2) | 0.43395(2) | 0.42150(2) | 0.01085(5) |
| Zn3 | 0.26991(2) | 0.02044(2) | 0.59357(2) | 0.01154(5) |
| Zn4 | −0.25437(2) | 0.46831(2) | 0.89893(2) | 0.01162(5) |
| S1 | 1.23935(3) | 0.01375(2) | 0.00699(2) | 0.01662(8) |
| S2 | 1.16429(3) | 0.22510(3) | −0.04588(2) | 0.01933(9) |
| S3 | 1.38694(3) | −0.03354(2) | 0.14090(2) | 0.01434(8) |
| S4 | 1.33166(3) | −0.21187(3) | 0.16243(2) | 0.02243(9) |
| S5 | 0.76166(3) | 0.49006(2) | 0.49145(2) | 0.01568(8) |
| S6 | 0.82759(3) | 0.28049(2) | 0.55427(2) | 0.01811(9) |
| S7 | 0.61060(3) | 0.54206(2) | 0.35999(2) | 0.01528(8) |
| S8 | 0.67151(3) | 0.71469(3) | 0.35391(2) | 0.02640(10) |
| S9 | 0.19049(3) | −0.00534(2) | 0.52636(2) | 0.01404(8) |
| S10 | 0.13376(3) | 0.20121(3) | 0.45112(2) | 0.02146(9) |
| S11 | 0.37827(3) | −0.09027(3) | 0.65260(2) | 0.01767(9) |
| S12 | 0.18010(3) | −0.14169(3) | 0.67108(2) | 0.02008(9) |
| S13 | −0.20078(3) | 0.51391(2) | 0.96891(2) | 0.01571(8) |
| S14 | −0.13417(3) | 0.30750(2) | 1.03947(2) | 0.01695(8) |
| S15 | −0.35606(3) | 0.56966(2) | 0.83013(2) | 0.01652(8) |
| S16 | −0.16391(3) | 0.62632(3) | 0.82114(2) | 0.02018(9) |
| P1 | 1.18693(3) | 0.11368(3) | −0.06241(2) | 0.01342(8) |
| P2 | 1.31363(3) | −0.10984(2) | 0.19258(2) | 0.01358(8) |
| P3 | 0.81163(3) | 0.39373(2) | 0.56375(2) | 0.01319(8) |
| P4 | 0.68508(3) | 0.62071(3) | 0.31560(2) | 0.01441(8) |
| P5 | 0.19564(3) | 0.08202(2) | 0.44657(2) | 0.01285(8) |
| P6 | 0.28871(3) | −0.14872(3) | 0.70786(2) | 0.01378(8) |
| P7 | −0.20182(3) | 0.42504(2) | 1.04798(2) | 0.01246(8) |
| P8 | −0.28551(3) | 0.65366(3) | 0.79243(2) | 0.01390(8) |
| O1 | 1.25043(8) | 0.09469(8) | −0.12815(5) | 0.0181(2) |
| O2 | 1.09596(8) | 0.10366(7) | −0.08057(5) | 0.0155(2) |
| O3 | 1.20573(8) | −0.04811(7) | 0.19927(6) | 0.0189(2) |
| O4 | 1.33449(9) | −0.12861(7) | 0.26423(5) | 0.0203(3) |
| O5 | 0.90597(8) | 0.40195(7) | 0.57791(5) | 0.0165(2) |
| O6 | 0.74914(8) | 0.41947(7) | 0.62839(5) | 0.0167(2) |
| O7 | 0.65535(9) | 0.65838(8) | 0.24594(6) | 0.0262(3) |
| O8 | 0.79198(8) | 0.55684(7) | 0.30699(6) | 0.0199(2) |
| O9 | 0.14869(8) | 0.06414(7) | 0.39520(5) | 0.0189(2) |
| O10 | 0.30703(8) | 0.05658(7) | 0.42120(5) | 0.0172(2) |
| O11 | 0.26206(8) | −0.11112(7) | 0.77138(5) | 0.0191(2) |
| O12 | 0.35364(8) | −0.24311(7) | 0.73409(5) | 0.0192(2) |
| O13 | −0.31136(8) | 0.44580(7) | 1.07637(5) | 0.0169(2) |
| O15 | −0.35500(8) | 0.74447(7) | 0.80511(5) | 0.0176(2) |
| O16 | −0.28275(9) | 0.66834(7) | 0.71725(5) | 0.0207(3) |
| N1 | 1.35491(9) | 0.15071(8) | 0.04131(6) | 0.0118(3) |
| N2 | 1.65809(9) | 0.39541(8) | −0.06228(6) | 0.0130(3) |
| N3 | 1.17131(9) | 0.13826(8) | 0.13849(6) | 0.0118(3) |
| N4 | 0.82489(9) | 0.36448(8) | 0.36108(6) | 0.0124(3) |
| N5 | 0.64200(9) | 0.35469(8) | 0.45698(6) | 0.0123(3) |
| N6 | 0.35574(10) | 0.09386(8) | 0.55467(6) | 0.0140(3) |
| N7 | 0.16944(9) | 0.09730(8) | 0.65171(6) | 0.0135(3) |
| N8 | −0.15272(9) | 0.38416(8) | 0.84627(6) | 0.0140(3) |
| C1 | 1.35002(12) | 0.08948(13) | −0.13911(8) | 0.0231(4) |
| H1A | 1.3884 | 0.0382 | −0.1122 | 0.028* |
| H1B | 1.3558 | 0.1396 | −0.1285 | 0.028* |
| C2 | 1.38477(12) | 0.08592(13) | −0.20826(8) | 0.0249(4) |
| H2A | 1.4524 | 0.0804 | −0.2169 | 0.037* |
| H2B | 1.3479 | 0.1379 | −0.2344 | 0.037* |
| H2C | 1.3767 | 0.0372 | −0.2185 | 0.037* |
| C3 | 1.00827(12) | 0.11942(11) | −0.03694(8) | 0.0198(4) |
| H3A | 0.9887 | 0.1763 | −0.0262 | 0.024* |
| H3B | 1.0177 | 0.0769 | 0.0028 | 0.024* |
| C4 | 0.93287(13) | 0.11388(12) | −0.06863(9) | 0.0241(4) |
| H4A | 0.8746 | 0.1188 | −0.0385 | 0.036* |
| H4B | 0.9554 | 0.0594 | −0.0827 | 0.036* |
| H4C | 0.9194 | 0.1598 | −0.1054 | 0.036* |
| C5 | 1.13063(13) | −0.08271(11) | 0.23007(9) | 0.0233(4) |
| H5A | 1.1402 | −0.1091 | 0.2748 | 0.028* |
| H5B | 1.1311 | −0.1263 | 0.2078 | 0.028* |
| C6 | 1.03745(13) | −0.01054(12) | 0.22719(11) | 0.0312(4) |
| H6A | 0.9851 | −0.0315 | 0.2480 | 0.047* |
| H6B | 1.0284 | 0.0145 | 0.1827 | 0.047* |
| H6C | 1.0381 | 0.0324 | 0.2489 | 0.047* |
| C7 | 1.41502(13) | −0.20013(12) | 0.28741(8) | 0.0254(4) |
| H7A | 1.4754 | −0.1890 | 0.2699 | 0.030* |
| H7B | 1.4180 | −0.2519 | 0.2742 | 0.030* |
| C8 | 1.40080(14) | −0.21147(13) | 0.35842(9) | 0.0293(4) |
| H8A | 1.4538 | −0.2596 | 0.3755 | 0.044* |
| H8B | 1.3407 | −0.2222 | 0.3752 | 0.044* |
| H8C | 1.3985 | −0.1601 | 0.3710 | 0.044* |
| C9 | 1.32977(11) | 0.22655(10) | 0.05775(7) | 0.0146(3) |
| H9 | 1.2708 | 0.2465 | 0.0837 | 0.018* |
| C10 | 1.38646(11) | 0.27678(10) | 0.03832(7) | 0.0147(3) |
| H10 | 1.3661 | 0.3304 | 0.0506 | 0.018* |
| C11 | 1.47346(11) | 0.24839(10) | 0.00074(7) | 0.0121(3) |
| C12 | 1.49854(11) | 0.17030(10) | −0.01740(7) | 0.0144(3) |
| H12 | 1.5568 | 0.1491 | −0.0437 | 0.017* |
| C13 | 1.43775(11) | 0.12459(10) | 0.00336(7) | 0.0151(3) |
| H13 | 1.4551 | 0.0719 | −0.0097 | 0.018* |
| C14 | 1.69316(11) | 0.31061(10) | −0.04750(7) | 0.0138(3) |
| H14 | 1.7604 | 0.2835 | −0.0519 | 0.017* |
| C15 | 1.63609(11) | 0.26108(10) | −0.02619(7) | 0.0138(3) |
| H15 | 1.6640 | 0.2013 | −0.0161 | 0.017* |
| C16 | 1.53709(11) | 0.29933(10) | −0.01947(7) | 0.0122(3) |
| C17 | 1.50051(11) | 0.38762(10) | −0.03381(7) | 0.0142(3) |
| H17 | 1.4336 | 0.4164 | −0.0291 | 0.017* |
| C18 | 1.56257(11) | 0.43241(10) | −0.05486(7) | 0.0149(3) |
| H18 | 1.5367 | 0.4923 | −0.0646 | 0.018* |
| C19 | 1.19221(11) | 0.13689(10) | 0.19559(7) | 0.0152(3) |
| H19 | 1.2552 | 0.1057 | 0.2054 | 0.018* |
| C20 | 1.12601(11) | 0.17894(10) | 0.24059(7) | 0.0150(3) |
| H20 | 1.1439 | 0.1769 | 0.2802 | 0.018* |
| C21 | 1.03300(11) | 0.22428(9) | 0.22757(7) | 0.0115(3) |
| C22 | 1.01116(11) | 0.22379(10) | 0.16881(7) | 0.0150(3) |
| H22 | 0.9480 | 0.2524 | 0.1585 | 0.018* |
| C23 | 1.08134(11) | 0.18166(10) | 0.12582(7) | 0.0146(3) |
| H23 | 1.0656 | 0.1833 | 0.0856 | 0.018* |
| C24 | 0.90555(11) | 0.30354(10) | 0.37904(8) | 0.0161(3) |
| H24 | 0.9160 | 0.2923 | 0.4221 | 0.019* |
| C25 | 0.97360(12) | 0.25674(11) | 0.33757(8) | 0.0168(3) |
| H25 | 1.0290 | 0.2136 | 0.3524 | 0.020* |
| C26 | 0.96097(11) | 0.27286(10) | 0.27370(7) | 0.0120(3) |
| C27 | 0.87777(11) | 0.33656(10) | 0.25522(7) | 0.0136(3) |
| H27 | 0.8663 | 0.3500 | 0.2122 | 0.016* |
| C28 | 0.81219(11) | 0.37998(10) | 0.29962(7) | 0.0140(3) |
| H28 | 0.7556 | 0.4227 | 0.2862 | 0.017* |
| C29 | 0.99217(12) | 0.37729(12) | 0.53321(8) | 0.0223(4) |
| H29A | 0.9835 | 0.4160 | 0.4917 | 0.027* |
| H29B | 1.0058 | 0.3192 | 0.5267 | 0.027* |
| C30 | 1.07310(13) | 0.38117(12) | 0.55961(10) | 0.0285(4) |
| H30A | 1.1309 | 0.3677 | 0.5289 | 0.043* |
| H30B | 1.0837 | 0.3402 | 0.5994 | 0.043* |
| H30C | 1.0577 | 0.4382 | 0.5678 | 0.043* |
| C31 | 0.64853(12) | 0.42862(12) | 0.63842(8) | 0.0209(4) |
| H31A | 0.6401 | 0.3811 | 0.6256 | 0.025* |
| H31B | 0.6120 | 0.4821 | 0.6126 | 0.025* |
| C32 | 0.61331(13) | 0.42894(13) | 0.70800(8) | 0.0251(4) |
| H32A | 0.5449 | 0.4378 | 0.7156 | 0.038* |
| H32B | 0.6246 | 0.4746 | 0.7206 | 0.038* |
| H32C | 0.6475 | 0.3746 | 0.7330 | 0.038* |
| C33 | 0.66389(15) | 0.60428(13) | 0.20259(9) | 0.0302(4) |
| H33A | 0.6199 | 0.5717 | 0.2192 | 0.036* |
| H33B | 0.7298 | 0.5639 | 0.1977 | 0.036* |
| C34 | 0.63928(16) | 0.65927(15) | 0.13969(9) | 0.0365(5) |
| H34A | 0.6484 | 0.6237 | 0.1087 | 0.055* |
| H34B | 0.6808 | 0.6936 | 0.1248 | 0.055* |
| H34C | 0.5726 | 0.6964 | 0.1445 | 0.055* |
| C35 | 0.87014(13) | 0.58892(12) | 0.28151(10) | 0.0253(4) |
| H35A | 0.8652 | 0.6341 | 0.3037 | 0.030* |
| H35B | 0.8682 | 0.6128 | 0.2357 | 0.030* |
| C36 | 0.96164(14) | 0.51656(14) | 0.29137(13) | 0.0410(5) |
| H36A | 1.0157 | 0.5368 | 0.2753 | 0.061* |
| H36B | 0.9665 | 0.4728 | 0.2684 | 0.061* |
| H36C | 0.9624 | 0.4928 | 0.3368 | 0.061* |
| C37 | 0.68047(11) | 0.27094(10) | 0.45769(7) | 0.0154(3) |
| H37 | 0.7473 | 0.2472 | 0.4460 | 0.018* |
| C38 | 0.62713(12) | 0.21808(10) | 0.47464(7) | 0.0156(3) |
| H38 | 0.6568 | 0.1595 | 0.4735 | 0.019* |
| C39 | 0.52927(11) | 0.25119(10) | 0.49348(7) | 0.0120(3) |
| C40 | 0.48985(12) | 0.33749(10) | 0.49479(8) | 0.0163(3) |
| H40 | 0.4239 | 0.3624 | 0.5087 | 0.020* |
| C41 | 0.54790(12) | 0.38616(10) | 0.47569(8) | 0.0164(3) |
| H41 | 0.5199 | 0.4451 | 0.4758 | 0.020* |
| C42 | 0.31778(12) | 0.17713(11) | 0.53288(8) | 0.0177(3) |
| H42 | 0.2508 | 0.2011 | 0.5323 | 0.021* |
| C43 | 0.37162(12) | 0.22940(10) | 0.51135(8) | 0.0171(3) |
| H43 | 0.3418 | 0.2879 | 0.4959 | 0.021* |
| C44 | 0.46981(11) | 0.19633(10) | 0.51232(7) | 0.0121(3) |
| C45 | 0.50950(11) | 0.10943(10) | 0.53377(8) | 0.0155(3) |
| H45 | 0.5764 | 0.0836 | 0.5342 | 0.019* |
| C46 | 0.45090(12) | 0.06141(10) | 0.55424(8) | 0.0164(3) |
| H46 | 0.4791 | 0.0024 | 0.5688 | 0.020* |
| C47 | 0.16451(13) | −0.01967(11) | 0.38450(9) | 0.0231(4) |
| H47A | 0.2152 | −0.0620 | 0.4090 | 0.028* |
| H47B | 0.1857 | −0.0221 | 0.3389 | 0.028* |
| C48 | 0.07433(15) | −0.03968(13) | 0.40481(10) | 0.0307(4) |
| H48A | 0.0843 | −0.0950 | 0.3953 | 0.046* |
| H48B | 0.0236 | 0.0037 | 0.3818 | 0.046* |
| H48C | 0.0559 | −0.0409 | 0.4506 | 0.046* |
| C49 | 0.33982(13) | 0.10112(12) | 0.36037(8) | 0.0223(4) |
| H49A | 0.3884 | 0.1231 | 0.3661 | 0.027* |
| H49B | 0.2857 | 0.1496 | 0.3437 | 0.027* |
| C50 | 0.38220(15) | 0.04084(14) | 0.31406(9) | 0.0313(4) |
| H50A | 0.4005 | 0.0713 | 0.2723 | 0.047* |
| H50B | 0.3350 | 0.0168 | 0.3105 | 0.047* |
| H50C | 0.4387 | −0.0047 | 0.3293 | 0.047* |
| C51 | 0.19425(13) | −0.13683(11) | 0.82225(8) | 0.0223(4) |
| H51A | 0.2178 | −0.1989 | 0.8364 | 0.027* |
| H51B | 0.1318 | −0.1204 | 0.8070 | 0.027* |
| C52 | 0.18396(18) | −0.09344(15) | 0.87613(10) | 0.0398(5) |
| H52A | 0.1377 | −0.1087 | 0.9108 | 0.060* |
| H52B | 0.1616 | −0.0321 | 0.8614 | 0.060* |
| H52C | 0.2458 | −0.1112 | 0.8915 | 0.060* |
| C53 | 0.38761(14) | −0.30803(12) | 0.69567(9) | 0.0293(4) |
| H53A | 0.3541 | −0.2876 | 0.6576 | 0.035* |
| H53B | 0.3731 | −0.3589 | 0.7203 | 0.035* |
| C54 | 0.49179(16) | −0.33073(14) | 0.67573(10) | 0.0380(5) |
| H54A | 0.5133 | −0.3757 | 0.6506 | 0.057* |
| H54B | 0.5250 | −0.3505 | 0.7134 | 0.057* |
| H54C | 0.5059 | −0.2810 | 0.6499 | 0.057* |
| C55 | 0.18965(12) | 0.09915(11) | 0.70812(8) | 0.0204(4) |
| H55 | 0.2488 | 0.0615 | 0.7215 | 0.025* |
| C56 | 0.12845(12) | 0.15330(11) | 0.74754(8) | 0.0209(4) |
| H56 | 0.1455 | 0.1522 | 0.7872 | 0.025* |
| C57 | 0.04136(11) | 0.20968(10) | 0.72896(7) | 0.0126(3) |
| C58 | 0.01973(12) | 0.20584(10) | 0.67108(7) | 0.0152(3) |
| H58 | −0.0395 | 0.2419 | 0.6570 | 0.018* |
| C59 | 0.08450(11) | 0.14955(10) | 0.63419(7) | 0.0149(3) |
| H59 | 0.0683 | 0.1478 | 0.5950 | 0.018* |
| C60 | −0.17993(12) | 0.36935(11) | 0.79679(8) | 0.0212(4) |
| H60 | −0.2438 | 0.3986 | 0.7881 | 0.025* |
| C61 | −0.11993(12) | 0.31394(11) | 0.75812(8) | 0.0205(4) |
| H61 | −0.1427 | 0.3052 | 0.7240 | 0.025* |
| C62 | −0.02559(11) | 0.27071(10) | 0.76937(7) | 0.0126(3) |
| C63 | 0.00256(11) | 0.28630(10) | 0.82059(7) | 0.0131(3) |
| H63 | 0.0662 | 0.2585 | 0.8300 | 0.016* |
| C64 | −0.06221(11) | 0.34229(10) | 0.85774(7) | 0.0134(3) |
| H64 | −0.0418 | 0.3514 | 0.8927 | 0.016* |
| C65 | −0.34049(13) | 0.39258(12) | 1.13352(8) | 0.0214(4) |
| H65A | −0.3909 | 0.4284 | 1.1613 | 0.026* |
| H65B | −0.2854 | 0.3600 | 1.1573 | 0.026* |
| C66 | −0.37756(13) | 0.33272(12) | 1.11585(9) | 0.0258(4) |
| H66A | −0.3968 | 0.2970 | 1.1545 | 0.039* |
| H66B | −0.3274 | 0.2970 | 1.0887 | 0.039* |
| H66C | −0.4327 | 0.3651 | 1.0929 | 0.039* |
| O14a | −0.16418(8) | 0.45149(8) | 1.10007(5) | 0.0177(2) |
| C67a | −0.06684(12) | 0.45251(12) | 1.08937(8) | 0.0222(4) |
| H67Aa | −0.0465 | 0.4669 | 1.0433 | 0.027* |
| H67Ba | −0.0227 | 0.3962 | 1.1062 | 0.027* |
| C68a | −0.0654(4) | 0.5181(3) | 1.1234(3) | 0.0296(11) |
| H68Aa | −0.1076 | 0.5739 | 1.1053 | 0.044* |
| H68Ba | −0.0003 | 0.5188 | 1.1181 | 0.044* |
| H68Ca | −0.0876 | 0.5041 | 1.1687 | 0.044* |
| O14′a | −0.16418(8) | 0.45149(8) | 1.10007(5) | 0.0177(2) |
| C67′a | −0.06684(12) | 0.45251(12) | 1.08937(8) | 0.0222(4) |
| H67Ca | −0.0347 | 0.4362 | 1.0479 | 0.027* |
| H67Da | −0.0305 | 0.4115 | 1.1231 | 0.027* |
| C68′a | −0.0699(4) | 0.5382(4) | 1.0899(3) | 0.0354(12) |
| H68Da | −0.1015 | 0.5778 | 1.0543 | 0.053* |
| H68Ea | −0.0048 | 0.5386 | 1.0858 | 0.053* |
| H68Fa | −0.1054 | 0.5554 | 1.1299 | 0.053* |
| C69 | −0.45037(12) | 0.77971(11) | 0.78591(8) | 0.0196(3) |
| H69A | −0.4768 | 0.7340 | 0.7907 | 0.023* |
| H69B | −0.4475 | 0.8080 | 0.7408 | 0.023* |
| C70 | −0.51284(13) | 0.84238(12) | 0.82716(8) | 0.0240(4) |
| H70A | −0.5745 | 0.8722 | 0.8111 | 0.036* |
| H70B | −0.4820 | 0.8832 | 0.8265 | 0.036* |
| H70C | −0.5228 | 0.8126 | 0.8708 | 0.036* |
| C71 | −0.21623(15) | 0.60301(13) | 0.68298(9) | 0.0331(5) |
| H71A | −0.2202 | 0.5470 | 0.7049 | 0.040* |
| H71B | −0.1502 | 0.6015 | 0.6814 | 0.040* |
| C72 | −0.24125(17) | 0.62239(13) | 0.61747(9) | 0.0331(5) |
| H72A | −0.1944 | 0.5810 | 0.5929 | 0.050* |
| H72B | −0.2410 | 0.6793 | 0.5970 | 0.050* |
| H72C | −0.3048 | 0.6196 | 0.6193 | 0.050* |
aOccupancy: 0.5.
Source of material
The Zn[S2P(OEt)2]2 precursor was prepared in high yield from the in situ reaction of Zn(NO3)2 ⋅ 6 H2O (Alfa Aesar; 14.87 g, 0.05 mol), EtOH (Merck; 12.25 mL, 0.21 mol), P2S5 (Sigma-Aldrich; 11.11 g, 0.05 mol) and 50% w/w NaOH solution (Merck; 8.80 mL, 0.11 mol). The title compound was obtained by mixing a suspension of this precursor (0.50 g, 1.15 mmol) and 4,4′-bipyridine (Merck; 0.18 g, 1.15 mmol) in dimethylformamide (Merck; 5 mL), followed by stirring for 30 min at 373 K. The solution was filtered and the filtrate was collected in a sample vial containing acetonitrile (Merck; 1 mL). Colourless blocks formed after one day. Yield: 0.46 g, (67.6%, based on Zn[S2P(OEt)2]2). M.pt (Stuart SMP 30 Melting point apparatus): 420.2–421.9 K. IR (Bruker Vertex 70 V equipped with Platinum ATR from 400 to 80 cm−1): 1057(w) ν(C—O); 940(s) ν(P—O); 667(s) ν(P—S)asym; 521(m) ν(P—S)sym; 294(m) ν(Zn—S); 380(w) ν(Zn—N).
Experimental details
The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The methyl-C68 atom was found, from refinement, to be statistically disordered over two positions with 50:50% site occupancy. Each position was modelled with independent anisotropic displacement parameters. Owing to poor agreement, one reflection, i.e. (7 0 2), was omitted from the final cycles of refinement. Translational pseudosymmetry is observed (<90%) but after careful analysis the refinement was carried out using the given unit cell.
Comment
The neutral, usually bidentate bridging ligand, 4,4′-bipyridine (4,4′-bipy), has proven to be a mainstay in coordination chemistry for the construction of coordination polymers, up to and including three-dimensional metal-organic framework architectures. An early aspiration of complexing zinc-triad 1,1-dithiolates, such as dithiophosphates [−S2P(OR)2], with 4,4′-bipy was the expectation that the aggregated precursor structures, through the agency of M⋯S bridging [5], would be assembled into higher-dimensional architectures via links provided by the 4,4′-bipy molecules. While complexation by 4,4′-bipy did occur, this was at the expense of M⋯S bridging so that, usually, only one-dimensional coordination polymers eventuated [6]. In the case of zinc dithiophosphates, {Zn[S2P(OR)2]2(4,4′-bipy)}n, one-dimensional, zig-zag polymers are formed when R = [7], Et [8] and iPr [9]. However, when the R group is bulky, such as when R = cyclohexyl (Cy), only zero-dimensional, binuclear molecules could be isolated, i.e. {Zn[S2P(OCy)2]2}2(4,4′-bipy) [10]. Such steric control over supramolecular association in the zinc-triad dithiophosphate adducts of bipyridyl-type molecules is well established [6], [10], [11], [12]. In continuation of studies in this area, a low temperature (100 K) form of {Zn[S2P(OEt)2]2(4,4′bipy)}n, (I), was characterised crystallographically and compared with the previously reported room-temperature form [8].
The asymmetric unit of (I) is shown in the figure (70% probability displacement ellipsoids; only one position for the statistically disordered C68 atom is shown) and comprises four independent Zn[S2P(OEt)2]2(4,4′-bipy) repeat units linked to form part of a one-dimensional coordination polymer with a zig-zag topology. The coordination environment for each zinc centre is approximately the same whereby each is coordinated by two sulphur atoms derived from two monodentate dithiophosphate ligands and two pyridyl-nitrogen atoms. The Zn—S(coordinating) bond lengths lie in the experimentally distinct range 2.2854(4) Å, for Zn4—S13, to 2.3519(4) Å, for Zn1—S3. Similarly, the Zn—N bond lengths span a range of over 0.045 Å, i.e. 2.0405(13) Å, for Zn1—N3, to 2.0879(13) Å, for Zn4—N2i (symmetry operation (i): −2 + x, y, 1 + z). Evidence that the dithiophosphate ligands are coordinating in a monodentate mode is seen in the non-bonding separations. For each repeat unit, one dithiophosphate ligand is orientated to place a thione-sulphur atom in close proximity to the zinc centre, whereas the other directs one of the ethoxy-oxygen atoms towards the zinc atom. An interesting trend is noted in the non-bonding-Zn⋯S, O separations in that the zinc atom forming the shortest Zn⋯S separation, forms the longest Zn⋯O separation, i.e. Zn4⋯S16 = 3.4445(5) Å and Zn4—O13 = 3.7553(11) Å, and vice versa, i.e. Zn2⋯S6 = 3.6248(4) Å and Zn2—O8 3.1598(12) Å; the other zinc centres follow the same trend but, with intermediate separations Zn3⋯S12 = 3.4964(5) Å and Zn3⋯O10 = 3.6291(11) Å, and Zn1⋯S2 = 3.5116(4) Å and Zn1⋯O3 = 3.2159(12) Å. The P—S bond lengths also exhibit definitive trends with those involving the coordinating sulphur atom being systematically longer (range 2.0190(5) Å, for P7—S13, to 2.0417(6) Å, for P8—S15) than those formed by the formally thione-sulphur atoms [range 1.9331(6) Å, for P8—S16, to 1.9470(6) Å, for P7—S14]. Interestingly, the shortest and longest P—S(thione) bonds involve atoms forming weak Zn⋯S and no Zn⋯S interactions, respectively, indicating no trend in the nature of the sulphur atom and the magnitude of the P=S bond. The coordination geometries for the zinc atoms are based on P2S2 donor sets which define approximate tetrahedra. By contrast to the bond lengths, systematic trends are lacking in the bond angles about the zinc atom. Thus, the bonds subtended by the coordinating sulphur atoms span a range of ca 10°, i.e. S5—Zn2—S7 = 109.371(16)° to S9—Zn3—S11 = 120.758(17)°, and those by the pyridyl-nitrogen atoms, ca 5°, i.e. N8—Zn4—N2i = 97.50(5)° to N1—Zn1—N3 = 102.09(5)°. However, despite these variations, the range of tetrahedral angles about the individual zinc atoms is narrow, being about 21° for the Zn4 atom [S15—Zn4—N2i = 97.15(4)° to S13—Zn4—S15 = 117.883(16)°] and about 23° for the Zn1 atom [S3—Zn1—N1 = 97.80(4)° to S1—Zn1—N3 = 120.32(4)°]. The twists between the pyridyl rings of the 4,4′-bipy molecules also differentiate the four repeat units with the dihedral angles between the N1-/N2-pyridyl [35.06(7)°], N3-/N4-pyridyl [17.40(8)°], N5-/N6-pyridyl [22.25(8)°] and N7-/N8-pyridyl [13.00(8)°] rings varying by over 20°.
In the crystal, the zig-zag chains run parallel to [2 0 −1]. The connections between the chains to consolidate the three-dimensional architecture are of the type C—H⋯O, C—H⋯S and C—H⋯π. Of each of these, the shortest and most directional interactions are pyridyl-C—H⋯O(ethoxy), pyridyl-C—H⋯S(coordinating) and methyl-C—H⋯π(pyridyl) [C56—H56⋯O1ii: H56⋯O1ii = 2.47 Å, C56⋯O1ii = 3.351(2) Å with angle at H56 = 153°, C38—H38⋯S9iii: H38⋯S9iii = 2.82 Å, C38⋯S9iii = 3.7031(17) Å with angle at H38 = 156° and C6—H6a⋯Cg(N7, C55—C59)iv: H6a⋯Cg(N7, C55—C59)iv = 2.85 Å, C6⋯Cg(N7, C55—C59)iv = 3.776(2) Å with angle at H6a = 158° for symmetry operations (ii) −1 + x, y, 1 + z, (iii) 1 − x, −y, 1 − z and (iv) 1 − x, −y, 1 − z].
The crystal of the room temperature (296 K) polymorph of (I) is also triclinic P1̅, with two independent repeat units of Zn[S2P(OEt)2]2(4,4′-bipy) in the asymmetric unit [8]. Similar coordination modes for the dithiophosphate ligands about each zinc atom, as described above, are apparent in the room-temperature form. The pitch in the zig-zag chains in (I) range from 16.2 to 17.5 Å, and match those in the literature precedent, i.e. 16.4 to 17.5 Å [8].
Finally, in an accompanying report, a low temperature (100 K) polymorph for {Cd[S2P(OEt)2]2(4,4′bipy)}n was described [13]. This, as was the room temperature (293 K) form [14], is a linear coordination polymer with a trans-N2S4 coordination geometry for the cadmium(II) centre. The obvious difference between the room- and low-temperature forms is in the number of Cd[S2P(OEt)2]2(4,4′-bipy) repeating units. In the former, the repeat unit lies on a centre of inversion, whereas in the latter, there are four independent repeat units, two in general positions and two with the cadmium atom lying on a centre of inversion.
Acknowledgements
Sunway University Sdn Bhd is thanked for financial support of this work through Grant no. STR-RCTR-RCCM-001-2019.
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©2019 Yee Seng Tan et al., published by De Gruyter, Berlin/Boston
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Artikel in diesem Heft
- 10.1515/ncrs-2020-frontmatter1
- The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
- The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
- Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
- Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
- The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
- Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
- Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
- Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
- The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
- Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
- Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
- The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
- Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
- The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
- The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
- The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
- The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
- Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
- Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
- The crystal structure of catena-poly(μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
- Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
- Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
- Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
- Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
- Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
- Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
- Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
- Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
- The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
- Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
- Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
- Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
- Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
- The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
- Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
- Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
- Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
- Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
- Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
- Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
- Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
- Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
- Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
- Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
- Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
- Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
- Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
- Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
- Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
- Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
- Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
- Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
- Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
- Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
- Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
- Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
- Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
- Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
- Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
- Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
- Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
- The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
- Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
- Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
- Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
- Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
- The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
- The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
- Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
- Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
- Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
- The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
- The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
- Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
- The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
- Crystal structure of 3-iodophthalic acid, C8H5IO4
- The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
- The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
- Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
- A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
Artikel in diesem Heft
- 10.1515/ncrs-2020-frontmatter1
- The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
- The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
- Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
- Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
- The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
- Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
- Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
- Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
- The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
- Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
- Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
- The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
- Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
- The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
- The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
- The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
- The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
- Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
- Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
- The crystal structure of catena-poly(μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
- Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
- Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
- Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
- Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
- Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
- Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
- Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
- Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
- The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
- Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
- Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
- Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
- Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
- The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
- Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
- Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
- Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
- Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
- Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
- Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
- Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
- Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
- Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
- Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
- Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
- Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
- Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
- Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
- Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
- Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
- Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
- Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
- Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
- Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
- Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
- Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
- Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
- Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
- Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
- Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
- Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
- The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
- Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
- Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
- Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
- Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
- The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
- The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
- Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
- Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
- Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
- The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
- The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
- Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
- The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
- Crystal structure of 3-iodophthalic acid, C8H5IO4
- The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
- The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
- Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
- A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n