Startseite Naturwissenschaften The crystal structure of (1R, 2R)-N1,N2-diferrocenyl-1,2-cyclohexanedicarboxamide, C28H30Fe2N2O2
Artikel Open Access

The crystal structure of (1R, 2R)-N1,N2-diferrocenyl-1,2-cyclohexanedicarboxamide, C28H30Fe2N2O2

  • Martin Zábranský , Zdeněk Leitner und Petr Štěpnička EMAIL logo
Veröffentlicht/Copyright: 18. Januar 2018
Artikel downloaden (PDF)
Veröffentlichen auch Sie bei De Gruyter Brill
Manuskript einreichen Informationen für Autor*innen
Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 233 Heft 2

Abstract

C28H30Fe2N2O2, monoclinic, P21 (no. 4), a = 10.7490(10) Å, b = 9.8370(8) Å, c = 11.9621(13) Å, β = 113.030(4)°, V = 1164.04(19) Å3, Z = 2, Rgt(F) = 0.0358, wRref(F2) = 0.0612, Flack parameter = −0.007(11), T = 150(2) K.

CCDC no.: 1590366

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Bar, orange
Size:0.27 × 0.07 × 0.07 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.28 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:28°, >99%
N(hkl)measured, N(hkl)unique, Rint:13446, 5616, 0.038
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4852
N(param)refined:307
Programs:SHELX [2, 3] , PLATON [4], Bruker programs [5, 6] ,
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
Fe10.88602(5)0.38170(5)0.79243(5)0.01641(13)
Fe20.52865(5)0.43236(5)0.11877(4)0.01371(12)
O10.5748(2)0.5912(2)0.7324(2)0.0183(6)
O20.4830(2)0.5837(2)0.3896(2)0.0194(6)
N10.5021(2)0.3849(3)0.6469(2)0.0133(6)
H1N0.5319520.3034230.6520440.016*
N20.4561(3)0.3549(3)0.3925(3)0.0142(7)
H2N0.4753290.2784650.3665290.017*
C10.3777(3)0.4357(4)0.5533(3)0.0144(7)
H10.3914840.5330350.5368120.017*
C20.3465(3)0.3537(4)0.4360(3)0.0156(8)
H20.3348780.2570550.4559040.019*
C30.2119(3)0.3977(4)0.3366(3)0.0216(10)
H3A0.2211810.4910980.3099230.026*
H3B0.1901710.3366490.2656590.026*
C40.0958(3)0.3944(4)0.3799(3)0.0255(10)
H4A0.0132080.4313050.3153660.031*
H4B0.0775070.2990440.3950930.031*
C50.1282(3)0.4765(4)0.4948(4)0.0225(9)
H5A0.0536050.4672830.5232760.027*
H5B0.1365050.5737440.4776670.027*
C60.2598(3)0.4276(5)0.5939(3)0.0181(8)
H6A0.2487850.3324400.6153040.022*
H6B0.2803210.4840740.6675040.022*
C110.7128(3)0.4004(4)0.8204(3)0.0179(9)
C120.8204(4)0.4715(4)0.9119(3)0.0224(9)
H120.8222560.5662820.9278440.027*
C130.9237(4)0.3778(5)0.9747(3)0.0265(10)
H131.0064720.3981021.0404340.032*
C140.8815(4)0.2480(4)0.9222(4)0.0284(10)
H140.9314800.1659720.9463430.034*
C150.7519(4)0.2618(4)0.8275(4)0.0212(9)
H150.7000420.1903820.7773290.025*
C160.8567(4)0.4890(5)0.6383(4)0.0279(10)
H160.7834320.5486900.5976090.033*
C170.9818(4)0.5257(4)0.7319(4)0.0309(11)
H171.0070850.6141270.7648900.037*
C181.0621(4)0.4070(5)0.7674(3)0.0297(11)
H181.1508440.4017070.8286680.036*
C190.9883(4)0.2989(4)0.6965(4)0.0275(10)
H191.0183250.2074610.7010420.033*
C200.8602(4)0.3493(4)0.6165(4)0.0277(11)
H200.7897070.2975620.5585950.033*
C210.5910(3)0.4667(4)0.7297(3)0.0146(8)
C310.6027(3)0.4477(4)0.3020(3)0.0154(8)
C320.6526(4)0.5572(4)0.2539(3)0.0170(9)
H320.6400520.6511800.2645310.020*
C330.7244(4)0.5017(4)0.1876(4)0.0223(10)
H330.7666800.5522300.1445580.027*
C340.7224(4)0.3584(4)0.1962(4)0.0215(10)
H340.7645040.2962330.1611450.026*
C350.6466(4)0.3236(4)0.2664(4)0.0187(9)
H350.6283040.2342640.2861540.022*
C360.3242(3)0.4290(5)0.0631(3)0.0218(8)
H360.2758880.4335410.1146970.026*
C370.3625(4)0.5403(4)0.0096(4)0.0215(9)
H370.3439850.6332120.0185620.026*
C380.4329(4)0.4905(4)−0.0593(3)0.0204(9)
H380.4710220.543687−0.1042290.024*
C390.4368(4)0.3484(4)−0.0498(4)0.0244(10)
H390.4771560.288360−0.0881090.029*
C400.3704(4)0.3096(4)0.0263(4)0.0247(10)
H400.3589580.2193240.0488270.030*
C410.5087(3)0.4666(4)0.3652(3)0.0143(8)

Source of material

Ferrocenecarboxylic acid (244 mg, 1.1 mmol) and 1-hydroxybenzotriazole (205 mg, 1.5 mmol) were dissolved in anhydrous dichlormethane (20 mL) by gentle heating in a reaction flask equipped with a stirring bar under an argon atmosphere. The solution was cooled on ice and neat 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (0.26 mL, 1.5 mmol) was introduced, causing the partly precipitated acid to redissolve. After stirring the mixture at 0 °C for 15 min, a dichloromethane solution of (1R, 2R)-1,2-diaminocyclohexane (60 mg, 0.50 mmol in 10 mL) was added and the stirring was continued at 0 °C 5 min and then at room temperature overnight. Then, the reaction mixture was washed with saturated aqueous NaHCO3 and brine (twice each), dried over anhydrous MgSO4, and evaporated under reduced pressure. The residue was purified by column chromatography over silica gel using dichloromethane-methanol (20:1) as the eluent. The first minor band containing [(1H-benzotriazol-1-yloxy)carbonyl]ferrocene [1] (63 mg, 17%) was followed by a major orange band due to the product. Following evaporation, the title compound was isolated as an orange amorphous solid (216 mg, 76%). Single crystals were grown by slow cooling of a methanolic solution.

1H NMR (CDCl3, 399.95 MHz): δ = 1.41 (m, 4 H), 1.83 (m, 2 H) and 2.25 (m, 2 H) (4 × CH2 of C6H10), 3.84 (m, 2 H, 2 × CH of C6H10), 4.09 (s, 10 H, C5H5), 4.30 (m, 4 H) and 4.70 (m, 4 H) (4 × CH of C5H4), 6.50 (d, 3JHH = 6.8 Hz, 2 H, NH) ppm 13C{1H} NMR (CDCl3, 100.58 MHz): δ = 24.79 (s, 2 C) and 32.66 (s, 2 C) (4 × CH2 in C6H10), 54.27 (s, 2 C, 2 × CH in C6H10), 68.18 (s, 2 C, CH of C5H4), 68.34 (s, 2 C, CH in C5H4), 69.73 (s, 10 C, C5H5), 70.53 (s, 4 C, CH of C5H4), 75.71 (s, 2 C, C—CO of C5H4), 171.31 (s, 2 C, C=O) ppm IR (Nujol): νmax = 3313 (br s, ν(NH)), 3228 (w), 3120 (w), 3096 (w), 3081 (m), 1625 (s, ν(C=O)), 1545 (s, δ(NH)), 1411 (m), 1353 (m), 1344 (m), 1320 (m), 1302 (s), 1273 (m), 1247 (w), 1221 (w), 1184 (m), 1140 (vw), 1108 (m), 1085 (vw), 1048 (vw), 1022 (m), 1015 (m), 1003 (m), 955 (vw), 928 (w), 888 (w), 865 (w), 821 (m), 812 (m), 773 (m), 762 (w), 648 (br w), 608 (vw), 584 (vw), 530 (w), 519 (m), 504 (m), 497 (m), 484 (m), 462 (m), 445 (w), 430 (vw) cm−1. MS (ESI+): m/z = 561.1 ([M + Na]+). Anal. Calc. for C28H30Fe2N2O2 (538.24 g⋅mol−1): C 62.48, H 5.62, N 5.21%. Found: C 62.15, H 5.68, N 5.04%.

Experimental details

The structure was solved by Direct methods using SHELXS-97 [2] and then refined by least-squares routine based on F2 (SHELXL-2017 [3]). Hydrogen atoms attached to nitrogen atoms were identified on the difference electron density maps and refined as riding atoms with Uiso(H) = 1.2 Ueq(N) [3]. All other hydrogen atoms were included in their calculated positions with Uiso(H) = 1.2 Ueq(C). The structural drawing and all numerical parameters discussed below were obtained with a recent version of the PLATON program [4]. The absolute configuration determined by anomalous dispersion [7] corresponded to that declared for the starting diamine (cf. Table 1).

Discussion

Carboxamides obtained from chiral diamines and phosphinocarboxylic acids emerged as efficient auxiliary ligands for a range enantioselective transition-metal catalyzed reactions [8]. In the chemistry of ferrocene-based ligands, compounds of this type are represented by amides obtained from 1,2-diaminocyclohexanes and planar-chiral 2-(diphenylphosphino)ferrocene-1-carboxylic acid [8], [9], [10]. Because none of these compound appears to have been structurally characterized, we decided to synthesize and characterize an analogous compound without the phosphine substituents at the ferrocene moieties, viz. (1R, 2R)-N1,N2-diferrocenyl-1,2-cyclohexanedicarboxamide. This compound was prepared by amidation of (1R, 2R)-diaminocyclohexane with ferrocenecarboxylic acid in the presence of peptide coupling agents [11] and was isolated as an orange solid in 76% yield by column chromatography. Chromatographic purification also afforded some [(1H-benzotriazol-1-yloxy)carbonyl]ferrocene, representing a non-consumed reaction intermediate.

The compound crystallizes in the non-centrosymmetric space group P21 and two molecules in the unit cell. The central six-membered ring in each dinuclear title complex has a chair conformation, which is manifested by the ring puckering coordinate θ [12] being 176.7(4)° (Note: ideal chair requires θ = 0° or 180°). The pivotal C—N bonds occupy equatorial positions and their length (C1—N1 = 1.456(4) Å, C2—N2 = 1.462(5) Å) as well as the N1—C21—C2—N2 torsion angle of −56.2(4)° are similar to those in the parent amine, (1R, 2R)-diaminocyclohexane [1.465(2) Å and −59.2(1)°, respectively] [13].

The ferrocene moieties in the title compound adopt the usual geometry with the individual Fe—C distances falling into narrow ranges, 2.025(4) Å (C11) to 2.056(3) Å (C13), and 2.024(3) Å (C31) to 2.053(5) Å (C33) for the ferrocene units comprising Fe1 and Fe2, respectively. Correspondingly, the dihedral angles subtended by the least-squares planes of the cyclopentadienyl rings are only 3.2(3)° (Fe1) and 3.7(3)° (Fe2). Even so, the amide substituents are rotated only slightly from the planes of their bonding cyclopentadienyl rings. In this case, however, a smaller departure from a coplanar arrangement is observed for the ferrocene unit comprising atom Fe1 that for the other ferrocene moiety (compare the angle between the {C21, N1, O1} and C(11−15) planes of 4.2(4)° with that subteneded by the planes {C41, N2, O2} and C(31−35) of 7.6(4)°). The amide planes are oriented so that their NH groups point to the same face of the cyclohexane ring. The dihedral angle subtended by the amide planes {C21, N1, O1} and {C41, N2, O2} is 79.6(5)°.

Adjacent molecules related by the crystallographic 21 screw axes are interconnected via pairs of N—H⋯O hydrogen bonds into infinite columnar stacks oriented in the direction of the crystallographic b axis (see Figure) [14]. These interactions are supported by the relatively weaker C—H⋯O interactions between the ferrocene CH groups adjacent to the amide NH (C15 and C35) as the donors and the amide C=O moieties as the acceptors. The hydrogen bond parameters are as follows: N1—H1N⋯O2i: N1⋯O2i = 3.008(4) Å, angle at H1N = 155°; N2—H2N⋯O1i: N2⋯O1i = 2.947(4) Å, angle at H2N = 154°; C15—H15⋯O2i: C15⋯O2i = 3.325(5) Å, angle at H15 = 158°; and C35—H35⋯O1i: C35⋯O1i = 3.304(5) Å, angle at H35 = 138°; where i = 1 − x, −1/2 + y, 1 − z.

Acknowledgements

Research leading to the presented results received support from the Czech Science Foundation (project no. 13-08890S). The authors are grateful to Dr. Ivana Císařová from the Department of Inorganic Chemistry, Faculty of Science, Charles University for collecting the diffraction data.

References

Kraatz, H.-B.; Lusztyk, J.; Enright, G. E.: Ferrocenoyl amino acids: a synthetic and structural study. Inorg. Chem. 36 (1997) 2400–2405.10.1021/ic961454tSuche in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar

Spek, A. L.: Structure validation in chemical crystallography. Acta Crystallogr. D65 (2009) 148–155.10.1107/S090744490804362XSuche in Google Scholar

SAINT, version 8.34A. Bruker AXS Inc., Madison, WI, USA (2013).Suche in Google Scholar

SADABS, version 2014/4. Bruker AXS Inc., Madison, WI, USA (2014).Suche in Google Scholar

Parsons, S.; Flack, H. D.; Wagner, T.: Use of intensity quotients and differences in absolute structure refinement. Acta Crystallogr. B69 (2013) 249–259.10.1107/S2052519213010014Suche in Google Scholar

Štěpnička, P.: Phosphinocarboxamides: the inconspicuous gems. Chem. Soc. Rev. 41 (2012) 4273–4305.10.1039/c2cs00001fSuche in Google Scholar

You, S.-L.; Hou, X.-L.; Dai, L.-X.; Cao, B.-X.; Sun, J.: Novel bis-N-[2-(diphenylphosphino)ferrocenylcarbonyl]diaminocyclohexane ligands: application in asymmetric allylic alkylation of imino esters with simple allyl carbonate. Chem. Commun. (2000) 1933–1934.10.1039/b003804kSuche in Google Scholar

Longmire, J. M.; Zhang, X.: Highly efficient kinetic resolution of 2-cyclohexenyl acetate in Pd-catalyzed allylic alkylation. Tetrahedron Lett. 41 (2000) 5435–5439.10.1016/S0040-4039(00)00844-3Suche in Google Scholar

El-Faham, A.; Albericio, F.: Peptide coupling reagents, more than a letter soup. Chem. Rev. 111 (2011) 6557–6602.10.1021/cr100048wSuche in Google Scholar PubMed

Cremer, D.; Pople, J. A.: General definition of ring puckering coordinates. J. Am. Chem. Soc. 97 (1975) 1354–1358.10.1021/ja00839a011Suche in Google Scholar

Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S.: Molecular recognition and self-assembly by “weak” hydrogen bonding: Unprecedented supramolecular helicate structures from diamine/diol motifs. J. Am. Chem. Soc. 116 (1994) 4495–4496.10.1021/ja00089a056Suche in Google Scholar

Motherwell, W. D. S.; Shields, G. P.; Allen, F. H.: Graph-set and packing analysis of hydrogen-bonded networks in polyamide structures in the Cambridge structural database. Acta Crystallogr. B56 (2000) 857–871.10.1107/S0108768100007230Suche in Google Scholar PubMed

Received: 2017-10-2
Accepted: 2017-12-11
Published Online: 2018-1-18
Published in Print: 2018-3-28

©2018 Martin Zábranský et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure and optical properties of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)praseodymium(III), C24H36N9O15Pr
  3. Crystal structure of dimethanol-bis(μ2-methanol-κ2O:O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}dimanganese(II), C38H38Mn2N2O14
  4. Crystal structure of catena-poly[diaqua-bis(μ2-2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ3O,O′:O′)calcium(II)], C56H48N4Ca2Cl8O12
  5. Crystal structure of catena-poly[triaqua-(isophthalato-κO)-(μ2-1,6-di(1H-imidazol-1-yl)hexane-κ2N:N′)]nickel(II), C20H28N4NiO7
  6. Crystal structure of cyclo[hexaqua-bis[1-[(2-ethyl-1H-imidazol-1-yl) methyl]-1H-benzotriazole-κ2N:N′]-bis(sulfato-κ1O)dicadmium(II)] monohydrate, C24H42Cd2N10O16S2
  7. Crystal Structure of bis(2-fluorbenzoato-κO)-bis(1,10-phenanthroline-κ2N,N′)manganese(II) dihydrate, C38H28F2MnN4O6
  8. Crystal structure of tetrapropylammonium 5-hydroxyisophthalate tetrahydrate, C20H41NO9
  9. Crystal structural of 2-amino-4-(3-bromophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C18H17BrN2O2
  10. Crystal structural of 2-amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C17H16N2O3
  11. Crystal structure of catena-poly[aqua(μ2-1,3-bis(1H-benzo[d]imidazol-1-yl)propane-κ2N:N′)-(μ2-5-(tert-butyl)isophthalate-κ3O,O′:O′′)nickel(II)], C29H30N4NiO5
  12. Crystal structure of catena-poly[(μ2-dicyanamido-κ2N:N′)-(μ2-2-(pyridin-2-yl)ethan-1-olato-κ3N,O:O′)copper(II)], C9H8CuN4O
  13. Crystal structure of bis(5,5′-((butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido-k4N,N′,N′′,N′′′)copper(II), C24H32CuN4O4
  14. The crystal structure of the formamide solvate of (17b)-estra-1,3,5(10)-triene-3,17diol, C19H27NO3
  15. Crystal structure of catena-poly[diaqua-bis(μ2-1H-benzo[d]imidazole-5-carboxylato-κ2N:O)nickel(II)] dihydrate, C16H18N4NiO8
  16. Crystal structure of dibromido[(1,2-bis(diisopropylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]nickel(II), C14H38B10NiBr2P2
  17. The crystal structure of catena-poly[aquachlorido(3,3′-([4,4′-bipyridine]-1,1′-diium-1,1′-diylbis(methylene))dibenzoato-κ2O:O′)copper(II)] chloride dihydrate, C26H26Cl2CuN2O7
  18. The crystal structure of N′-(2-nitrobenzylidene)-2-phenylacetohydrazide, C15H13N3O3
  19. Crystal structure of dichlorido bis[1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κ1N]cadmium(II), C30H26CdCl2N10
  20. Crystal structure of aqua-bis(3-(2-pyridyl)-5-(4-pyridyl)-1H-1,2,4-triazole-κ2N,N′)copper(II) sulfate tetrahydrate, C24H28CuN10O9S
  21. Crystal structure of dibromido-carbonyl-(η6-p-cymene)osmium(II), C11H14Br2OOs
  22. Crystal structure of catena-poly[chlorido-(μ2-chlorido)-bis(imidazole-κN)copper(II)] C6H8Cl2CuN4
  23. Crystal structure of [(1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]dibromidonickel(II)), C26H54B10NiBr2P2
  24. Crystal structure of dichlorido[1,1′-bis(diphenylphosphanyl)ferrocene-κ2P,P′]zinc(II), C34H28FeCl2P2Zn
  25. Crystal structure of tris(μ2-2-(pyridin-2-yl)ethan-1-olato-κ3N,O:O)-trithiocyanato-κN-dicobalt(III), C24H24Co2N6O3S3
  26. The crystal structure of diaqua-2,2′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))diphenolato-κ4N,N′,O,O′)manganese(III) perchlorate, C20H24MnClN2O4
  27. Crystal structure of bis(μ3-chlorido)-bis(μ2-chlorido)-tetrakis(μ2-2,6-bis (diphenylmethyl)-4-t-butylphenolato)tetralithium(I)dicobalt(II) toluene solvate, C75.5H70Cl2CoLi2O2
  28. The crystal structure of hexaaqua-bis(μ2-3-(3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl)propanoato-κ2O:O′)-tetrakis(3-(3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl)propanoato-κO)dierbium(III) octahydrate, C60H76N18O32Er2
  29. Crystal structure of dimethylammonium bis(naphthalene-2,3-diolato)borate, C22H20BNO4
  30. Crystal structure of 2-amino-4-(4-nitro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H17N3O4
  31. The crystal structure of (E)-4-chloro-2-(((5-methylpyridin-2-yl)imino)methyl)phenol, C13H11ClN2O
  32. Crystal structure of bis(N,N,N-trimethylbutanaminium) poly[heptaselenidotristannate(IV)], C14H36N2Se7Sn3
  33. The crystal structure of N-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide, C28H35N3S
  34. Crystal structure of 2-(4-chlorophenyl)-2,3-dihydro-1H-perimidine, C17H13Cl1N2
  35. The Crystal structure of 2-iodo-1-(p-tolyl)propan-1-one, C10H11IO
  36. Crystal structure of ethyl 1-(4-bromobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17BrN2O2
  37. Crystal structure of ethyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17FN2O2
  38. Crystal structure of catena-poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C8H8O8Cd
  39. Crystal structure of tetraaqua-bis[6-(1H-imidazol-1-yl-κN)nicotinato]zinc(II), C18H20N6O8Zn
  40. Crystal structure of dichlorido-bis(N-phenyl-2-(quinolin-8-yloxy)acetamide-κ2N,O) – acetone (2/1), C35.5H31N4O4.5Cl2Cu
  41. Crystal Structure of ethyl (E)-3,4-dimethyl-5-((2-(4-methylbenzoyl)hydrazono)methyl)-1H-pyrrole-2-carboxylate — water — ethanol (1/1/1), C20H29N3O5
  42. Crystal structure of 5-((4-(1H-benzo[d]imidazol-2-yl)-2-methoxyphenoxy)methyl)-2-chlorothiazole - trichloromethane - methanol (1/1/1), C20H19Cl4N3O3S
  43. The crystal structure of a matrine derivative: 41S,7aS,12S,13aR,13bR)-12-(4-methylpiperazin-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one, C20H34N4O
  44. Crystal structure of cesium beryllophosphate, Be3Cs2P4O14
  45. Crystal Structure of 3-((3-hydroxybenzyl)ammonio)-3-phenylpropanoate, C16H17NO3
  46. Crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride — 4-hydroxy-3-methoxybenzoic acid — water (2/1/5), C48H54N2Cl2O17
  47. The crystal structure of (1R, 2R)-N1,N2-diferrocenyl-1,2-cyclohexanedicarboxamide, C28H30Fe2N2O2
  48. Crystal structure of N-(2-methylphenyl)ethoxycarbothioamide, C10H13NOS
  49. Crystal Structure of ethyl (E)-2,4-dimethyl-5-((2-tosylhydrazono)methyl)-1H-pyrrole-3-carboxylate monohydrate, C17H23N3O5
  50. Crystal structure of Diiodo-(N′-((quinolin-8-yl)methylene)isonicotinohydrazide κ3N,N′,O)cadium(II) – dimethylformamide (1/1), C19H19N5O2CdI2
  51. Crystal structure of dinitrato-(N′-((quinolin-8-yl)methylene)isonicotinohydrazide κ3-N,N′,O)copper(II), C16H12N6O7Cu
  52. Crystal structure of benzoato-κO-bis(1,3,5-triaza-7-phosphaadamantane-κP)silver(I) monohydrate C19H31AgN6O3P2
  53. Crystal structure of (E)-2-(anthracen-9-ylmethylene)hydrazine-1-carbothioamide, C16H13N3S
  54. The crystal structure of 8-chloro-7-ethyl-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione, C9H11ClN4O2
  55. Crystal structure of {5,5′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′}zinc(II), C23H30N4O4Cu
  56. Crystal structure of bis(4-dimethylamino-pyridin-1-ium)tetrafluorosuccinate, C18H22F4N4O4
  57. Crystal structure of dimethyl 3,9-dibenzyl-6,12-dicyclohexyl-3,9-diazahexacyclo [6.4.0.02,7.04,11.05,10]-dodecane-1,11-dicarboxylate, C40H50N2O4
  58. Crystal structure of diethyl 3,9-diphenyl-6,12-bis(3-methoxyphenyl)-3,9-diazahexacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,11-dicarboxylate, C42H42N2O6
  59. Crystal structure of bis(acetato-κO)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)nickel(II), C18H22N4NiO6
  60. Crystal structure of (N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3N,O,O′)-diphenyltin(IV), C28H23FN2O3Sn
  61. Crystal structure of {N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3O,N,O′}dimethyltin(IV), C18H19FN2O3Sn
https://doi.org/10.1515/ncrs-2017-0294
Creative Commons
BY-NC-ND 4.0

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure and optical properties of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)praseodymium(III), C24H36N9O15Pr
  3. Crystal structure of dimethanol-bis(μ2-methanol-κ2O:O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}dimanganese(II), C38H38Mn2N2O14
  4. Crystal structure of catena-poly[diaqua-bis(μ2-2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ3O,O′:O′)calcium(II)], C56H48N4Ca2Cl8O12
  5. Crystal structure of catena-poly[triaqua-(isophthalato-κO)-(μ2-1,6-di(1H-imidazol-1-yl)hexane-κ2N:N′)]nickel(II), C20H28N4NiO7
  6. Crystal structure of cyclo[hexaqua-bis[1-[(2-ethyl-1H-imidazol-1-yl) methyl]-1H-benzotriazole-κ2N:N′]-bis(sulfato-κ1O)dicadmium(II)] monohydrate, C24H42Cd2N10O16S2
  7. Crystal Structure of bis(2-fluorbenzoato-κO)-bis(1,10-phenanthroline-κ2N,N′)manganese(II) dihydrate, C38H28F2MnN4O6
  8. Crystal structure of tetrapropylammonium 5-hydroxyisophthalate tetrahydrate, C20H41NO9
  9. Crystal structural of 2-amino-4-(3-bromophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C18H17BrN2O2
  10. Crystal structural of 2-amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C17H16N2O3
  11. Crystal structure of catena-poly[aqua(μ2-1,3-bis(1H-benzo[d]imidazol-1-yl)propane-κ2N:N′)-(μ2-5-(tert-butyl)isophthalate-κ3O,O′:O′′)nickel(II)], C29H30N4NiO5
  12. Crystal structure of catena-poly[(μ2-dicyanamido-κ2N:N′)-(μ2-2-(pyridin-2-yl)ethan-1-olato-κ3N,O:O′)copper(II)], C9H8CuN4O
  13. Crystal structure of bis(5,5′-((butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido-k4N,N′,N′′,N′′′)copper(II), C24H32CuN4O4
  14. The crystal structure of the formamide solvate of (17b)-estra-1,3,5(10)-triene-3,17diol, C19H27NO3
  15. Crystal structure of catena-poly[diaqua-bis(μ2-1H-benzo[d]imidazole-5-carboxylato-κ2N:O)nickel(II)] dihydrate, C16H18N4NiO8
  16. Crystal structure of dibromido[(1,2-bis(diisopropylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]nickel(II), C14H38B10NiBr2P2
  17. The crystal structure of catena-poly[aquachlorido(3,3′-([4,4′-bipyridine]-1,1′-diium-1,1′-diylbis(methylene))dibenzoato-κ2O:O′)copper(II)] chloride dihydrate, C26H26Cl2CuN2O7
  18. The crystal structure of N′-(2-nitrobenzylidene)-2-phenylacetohydrazide, C15H13N3O3
  19. Crystal structure of dichlorido bis[1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κ1N]cadmium(II), C30H26CdCl2N10
  20. Crystal structure of aqua-bis(3-(2-pyridyl)-5-(4-pyridyl)-1H-1,2,4-triazole-κ2N,N′)copper(II) sulfate tetrahydrate, C24H28CuN10O9S
  21. Crystal structure of dibromido-carbonyl-(η6-p-cymene)osmium(II), C11H14Br2OOs
  22. Crystal structure of catena-poly[chlorido-(μ2-chlorido)-bis(imidazole-κN)copper(II)] C6H8Cl2CuN4
  23. Crystal structure of [(1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]dibromidonickel(II)), C26H54B10NiBr2P2
  24. Crystal structure of dichlorido[1,1′-bis(diphenylphosphanyl)ferrocene-κ2P,P′]zinc(II), C34H28FeCl2P2Zn
  25. Crystal structure of tris(μ2-2-(pyridin-2-yl)ethan-1-olato-κ3N,O:O)-trithiocyanato-κN-dicobalt(III), C24H24Co2N6O3S3
  26. The crystal structure of diaqua-2,2′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))diphenolato-κ4N,N′,O,O′)manganese(III) perchlorate, C20H24MnClN2O4
  27. Crystal structure of bis(μ3-chlorido)-bis(μ2-chlorido)-tetrakis(μ2-2,6-bis (diphenylmethyl)-4-t-butylphenolato)tetralithium(I)dicobalt(II) toluene solvate, C75.5H70Cl2CoLi2O2
  28. The crystal structure of hexaaqua-bis(μ2-3-(3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl)propanoato-κ2O:O′)-tetrakis(3-(3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl)propanoato-κO)dierbium(III) octahydrate, C60H76N18O32Er2
  29. Crystal structure of dimethylammonium bis(naphthalene-2,3-diolato)borate, C22H20BNO4
  30. Crystal structure of 2-amino-4-(4-nitro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H17N3O4
  31. The crystal structure of (E)-4-chloro-2-(((5-methylpyridin-2-yl)imino)methyl)phenol, C13H11ClN2O
  32. Crystal structure of bis(N,N,N-trimethylbutanaminium) poly[heptaselenidotristannate(IV)], C14H36N2Se7Sn3
  33. The crystal structure of N-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-4-methylbenzenesulfonamide, C28H35N3S
  34. Crystal structure of 2-(4-chlorophenyl)-2,3-dihydro-1H-perimidine, C17H13Cl1N2
  35. The Crystal structure of 2-iodo-1-(p-tolyl)propan-1-one, C10H11IO
  36. Crystal structure of ethyl 1-(4-bromobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17BrN2O2
  37. Crystal structure of ethyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C19H17FN2O2
  38. Crystal structure of catena-poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C8H8O8Cd
  39. Crystal structure of tetraaqua-bis[6-(1H-imidazol-1-yl-κN)nicotinato]zinc(II), C18H20N6O8Zn
  40. Crystal structure of dichlorido-bis(N-phenyl-2-(quinolin-8-yloxy)acetamide-κ2N,O) – acetone (2/1), C35.5H31N4O4.5Cl2Cu
  41. Crystal Structure of ethyl (E)-3,4-dimethyl-5-((2-(4-methylbenzoyl)hydrazono)methyl)-1H-pyrrole-2-carboxylate — water — ethanol (1/1/1), C20H29N3O5
  42. Crystal structure of 5-((4-(1H-benzo[d]imidazol-2-yl)-2-methoxyphenoxy)methyl)-2-chlorothiazole - trichloromethane - methanol (1/1/1), C20H19Cl4N3O3S
  43. The crystal structure of a matrine derivative: 41S,7aS,12S,13aR,13bR)-12-(4-methylpiperazin-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one, C20H34N4O
  44. Crystal structure of cesium beryllophosphate, Be3Cs2P4O14
  45. Crystal Structure of 3-((3-hydroxybenzyl)ammonio)-3-phenylpropanoate, C16H17NO3
  46. Crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride — 4-hydroxy-3-methoxybenzoic acid — water (2/1/5), C48H54N2Cl2O17
  47. The crystal structure of (1R, 2R)-N1,N2-diferrocenyl-1,2-cyclohexanedicarboxamide, C28H30Fe2N2O2
  48. Crystal structure of N-(2-methylphenyl)ethoxycarbothioamide, C10H13NOS
  49. Crystal Structure of ethyl (E)-2,4-dimethyl-5-((2-tosylhydrazono)methyl)-1H-pyrrole-3-carboxylate monohydrate, C17H23N3O5
  50. Crystal structure of Diiodo-(N′-((quinolin-8-yl)methylene)isonicotinohydrazide κ3N,N′,O)cadium(II) – dimethylformamide (1/1), C19H19N5O2CdI2
  51. Crystal structure of dinitrato-(N′-((quinolin-8-yl)methylene)isonicotinohydrazide κ3-N,N′,O)copper(II), C16H12N6O7Cu
  52. Crystal structure of benzoato-κO-bis(1,3,5-triaza-7-phosphaadamantane-κP)silver(I) monohydrate C19H31AgN6O3P2
  53. Crystal structure of (E)-2-(anthracen-9-ylmethylene)hydrazine-1-carbothioamide, C16H13N3S
  54. The crystal structure of 8-chloro-7-ethyl-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione, C9H11ClN4O2
  55. Crystal structure of {5,5′-((propane-1,3-diylbis(azanylylidene))bis(methanylylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′}zinc(II), C23H30N4O4Cu
  56. Crystal structure of bis(4-dimethylamino-pyridin-1-ium)tetrafluorosuccinate, C18H22F4N4O4
  57. Crystal structure of dimethyl 3,9-dibenzyl-6,12-dicyclohexyl-3,9-diazahexacyclo [6.4.0.02,7.04,11.05,10]-dodecane-1,11-dicarboxylate, C40H50N2O4
  58. Crystal structure of diethyl 3,9-diphenyl-6,12-bis(3-methoxyphenyl)-3,9-diazahexacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,11-dicarboxylate, C42H42N2O6
  59. Crystal structure of bis(acetato-κO)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)nickel(II), C18H22N4NiO6
  60. Crystal structure of (N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3N,O,O′)-diphenyltin(IV), C28H23FN2O3Sn
  61. Crystal structure of {N-(3-ethoxy-2-oxidobenzylidene)-4-fluorobenzohydrazonato-κ3O,N,O′}dimethyltin(IV), C18H19FN2O3Sn
Jetzt anmelden und 20% sparen
Institutioneller Zugang
Wie funktioniert Authentifizierung?
Haben Sie eine Idee, wie wir unsere Website verbessern können?
Bitte schreiben Sie uns.
© 2025 De Gruyter Brill
Heruntergeladen am 19.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2017-0294/html
Button zum nach oben scrollen