Crystal structure of 2-tert-butyl 1-methyl 5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate, C19H24N2O6
-
Ignez Caracelli
, Julio Zukerman-Schpector
Abstract
C19H24N2O6, monoclinic, P21 (no. 4), a = 8.3611(7) Å, b = 9.0521(8) Å, c = 13.8988(8) Å, β = 106.710(5)°, V = 1007.52(14) Å3, Z = 2, Rgt(F) = 0.0428, wRref(F2) = 0.1174, T = 293(2) K.
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 irregular |
Size: | 0.40 × 0.32 × 0.30 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.09 mm−1 |
Diffractometer, scan mode: | Enraf Nonius TurboCAD4, ω |
θmax, completeness: | 30.0°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 3294, 3105, 0.025 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 1902 |
N(param)refined: | 252 |
Programs: | Absorption correction [1], CAD4 [2], [3], SIR2014 [3], SHELX [4], WinGX/ORTEP [5], [6] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
O1 | 0.8580(3) | 0.2321(3) | 0.83858(15) | 0.0741(7) |
O2 | 0.9732(2) | 0.1773(3) | 1.00129(15) | 0.0619(6) |
O3 | 0.2235(2) | 0.8167(2) | 0.82843(12) | 0.0528(5) |
O4 | 0.1395(2) | 0.9078(2) | 0.67070(12) | 0.0467(4) |
O5 | −0.2428(3) | 0.7926(3) | 0.49100(13) | 0.0712(7) |
O6 | −0.2030(2) | 0.7842(2) | 0.65798(12) | 0.0506(5) |
N1 | 0.1019(2) | 0.6687(2) | 0.69561(14) | 0.0383(5) |
N2 | 0.7240(3) | 0.2746(3) | 0.95713(15) | 0.0472(5) |
H2N | 0.744(4) | 0.268(4) | 1.0207(8) | 0.057* |
C2 | 0.0947(3) | 0.5385(3) | 0.75698(18) | 0.0424(6) |
H2 | 0.038132 | 0.564133 | 0.807465 | 0.051* |
C3 | −0.0151(3) | 0.4382(3) | 0.6794(2) | 0.0525(7) |
H3 | −0.043306 | 0.342534 | 0.692777 | 0.063* |
C4 | −0.0667(3) | 0.5012(3) | 0.5903(2) | 0.0526(7) |
H4 | −0.130411 | 0.453836 | 0.532597 | 0.063* |
C5 | −0.0102(3) | 0.6580(3) | 0.59370(17) | 0.0432(6) |
H5 | 0.049966 | 0.675981 | 0.543850 | 0.052* |
C6 | 0.2642(3) | 0.4717(3) | 0.80829(17) | 0.0401(6) |
C7 | 0.3145(3) | 0.4508(3) | 0.91076(19) | 0.0507(7) |
H7 | 0.244804 | 0.480145 | 0.948715 | 0.061* |
C8 | 0.4675(4) | 0.3866(4) | 0.95817(18) | 0.0521(7) |
H8 | 0.499965 | 0.374117 | 1.027515 | 0.062* |
C9 | 0.5718(3) | 0.3411(3) | 0.90275(17) | 0.0410(6) |
C10 | 0.5229(3) | 0.3608(3) | 0.79963(18) | 0.0478(6) |
H10 | 0.592410 | 0.331157 | 0.761632 | 0.057* |
C11 | 0.3689(3) | 0.4252(3) | 0.75330(18) | 0.0488(7) |
H11 | 0.335716 | 0.437174 | 0.683917 | 0.059* |
C12 | 0.8510(3) | 0.2300(3) | 0.92356(19) | 0.0442(6) |
C13 | 1.1159(4) | 0.1162(5) | 0.9779(3) | 0.0795(11) |
H13A | 1.157505 | 0.186115 | 0.938982 | 0.119* |
H13B | 1.084193 | 0.026899 | 0.939908 | 0.119* |
H13C | 1.201381 | 0.094735 | 1.038989 | 0.119* |
C14 | 0.1593(3) | 0.7982(3) | 0.73947(17) | 0.0402(5) |
C15 | 0.1852(5) | 1.0529(4) | 0.7103(2) | 0.0657(9) |
H15A | 0.294475 | 1.049917 | 0.757550 | 0.099* |
H15B | 0.105933 | 1.086856 | 0.743443 | 0.099* |
H15C | 0.185825 | 1.119081 | 0.656452 | 0.099* |
C16 | −0.1659(3) | 0.7561(3) | 0.57373(17) | 0.0445(6) |
C17 | −0.3580(4) | 0.8624(4) | 0.6599(2) | 0.0630(8) |
C18 | −0.3480(6) | 0.8569(7) | 0.7699(3) | 0.1032(16) |
H18A | −0.243749 | 0.898392 | 0.808747 | 0.155* |
H18B | −0.355352 | 0.756109 | 0.789784 | 0.155* |
H18C | −0.438546 | 0.912611 | 0.781328 | 0.155* |
C19 | −0.3512(7) | 1.0175(5) | 0.6252(4) | 0.1066(16) |
H19A | −0.352571 | 1.017469 | 0.555906 | 0.160* |
H19B | −0.250620 | 1.063784 | 0.664983 | 0.160* |
H19C | −0.446195 | 1.071129 | 0.632398 | 0.160* |
C20 | −0.5075(4) | 0.7776(7) | 0.5956(3) | 0.1069(16) |
H20A | −0.495320 | 0.674701 | 0.612835 | 0.160* |
H20B | −0.514028 | 0.789744 | 0.525981 | 0.160* |
H20C | −0.607720 | 0.814841 | 0.607453 | 0.160* |
Source of material
To a solution of 2-tert-butyl 1-methyl (2S)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate (91 mg, 0.40 mol) in dry acetonitrile (2.5 mL), under an inert atmosphere, were added quickly and consecutively anhydrous NaOAc (98 mg, 1.195 mmol), [4-MeOCONHC6H4N2]BF4 (106 mg, 0.40 mmol, M.pt = 415–416 K; recrystallised from acetone/ether) and Pd2(dba)3⋅dba (5.0 mg, 0.0043 mmol; dba = dibenzylideneacetone). The mixture was stirred at room temperature for 45 min; the progress of the reaction was followed by the release of nitrogen. Then, EtOAc (5.0 mL) and a saturated solution (3.0 mL) of NaHCO3 were added. The mixture was stirred for 5 min and the phases were separated. The organic phase was washed with water and then with a saturated solution of NaCl. The solution was then dried with anhydrous Na2SO4, filtered and the solvent was removed in a rotary evaporator. The residue was purified by filtration through a layer of silica gel, using a mixture of EtOAc/n-hexane (2:8) as the eluent. Yield: 148 mg (98%) of Heck products. The products were not separable by flash column chromatography on silica gel, produced a single “spot” by thin layer chromatography and a single signal by capillary gas chromatography. Therefore, the product was dissolved in DMSO and allowed to crystallize slowly. The trans diastereoisomer, (I), precipitated; the cis diastereoisomer remained in solution.
Suitable crystals for the X-ray diffraction analysis were obtained by slow evaporation from a MeOH solution. M. pt: 453–456 K.
The 1H and 13C NMR spectra reflect the presence of conformational rotamers in solution. 1H NMR (300 MHz, DMSO-d6 r.t.): δ = 9.62 and 9.61 (2 br s, 1H); 7.39 (d, J = 8.1 Hz, 1H); 7.37 (d, J = 8.4 Hz, 1H); 7.15 (d, J = 8.4 Hz, 1H); 7.13 (d, J = 8.4 Hz, 1H); 5.95 and 5.93 and 5.91 [(t, J = 1.9 Hz) + (t, J = 1.9 Hz) + (t, J = 1.6 Hz), 1H]; 5.88 and 5.86 (2q, J = 2.2 Hz, 1H); 5.53–5.44 (m, 1H); 5.07 and 5.05 [(t, J = 2.2 or 1.6 Hz) + (t, J = 1.9 Hz), 1H]; 3.65 (s, 3H); 3.48 and 3.39 (2s, 3H); 1.422 and 1.415 (2s, 9H). 1H NMR (300 MHz, DMSO-d6, T = 393 K): δ = 9.05 (br s, 1H); 7.39 (d, J = 8.4 Hz, 2H); 7.14 (d, J = 8.4 Hz, 2H); 5.93 and 5.91 (2t, J = 2.2 or 1.5 Hz, 1H); 5.86 and 5.84 (2t, J = 2.2 or 1.8 Hz, 1H); 5.55-5.48 (m, 1H); 5.05 and 5.03 (2t, J = 2.2 or 1.8 Hz, 1H); 3.68 (s, 3H); 3.49 (s, 3H); 1.46 (s, 9H). 13C NMR (75 MHz, DMSO-d6, T = 393 K): δ = 167.9; 153.4; 137.6; 134.2; 133.4; 126.2; 122.8; 118.1; 80.5; 67.4; 67.2; 51.0; 50.6; 27.0. HRMS (Electron Impact Ionisation) calculated for C19H24N2O6: 376.16344; found: 376.16320.
Experimental details
The C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The N-bound H atom was refined with N—H = 0.86 ± 0.01 Å, and with 1.2Ueq(N). The absolute structure was not determined in the X-ray experiment but, the assignment of stereochemistry at the chiral centres is based on the chirality of the synthetic precursor employed in the synthesis.
Comment
Recent reports have detailed the crystal structure determinations of pyrrole [7] and pyrrolidine [8], [9] derivatives having rare or even unprecented substitution patterns. These are crucial intermediates for the synthesis of pharmacologically-relevant molecules via Heck-Matsuda arylation reactions, namely the coupling of an olefin with an arenediazonium salt mediated by a catalytic palladium complex [10]. In the present case, the title compound, (I), is an intermediate in the enantioselective synthesis of polyhydroxylated pyrrolidines such as analogues of Schramm’s antiprotozoan C-azanucleoside [11], which may display anti-viral, anti-cancer and anti-microbial activities [12], [13]. Herein, the crystal and molecular structures of (I) are described along with an additional analysis of the molecular packing via calculated Hirshfeld surfaces.
The molecular structure of (I) is illustrated in the figure (35% displacement ellipsoids) and features a five-membered ring which is twisted about the N1—C5 bond. The geometry about the N1 atom is close to trigonal with the sum of the angles subtended at N1 = 356.2°. The ring is tri-substituted, with a N1-bound methyloxycarbonyl group flanked on either side by a C2-bound [(methoxycarbonyl)amino]phenyl substituent and a C5-bound tert-butyloxycarbonyl group. The configuration at each of the C2 and C5 atoms is S. The dihedral angle between the N1-substituent and the best plane through the pyrrole ring is 14.91(14)°, being indicative of a twist between the residues. As indicated above, the C2- and C5-bound substituents lie to the opposite side of the pyrrole ring. In fact, they have approximately orthogonal dispositions to the pyrrole ring, forming dihedral angles of 87.83(9) and 83.42(13)°, respectively, with the former. The [(methoxycarbonyl)amino]phenyl is close to planar with the C6/C2NO2 dihedral angle being 2.97(15)°.
There is a single, direct literature precedent for pyrrole (I) which has only been recently described [7]. Here, the N1 atom carries a tert-butyloxycarbonyl group and is flanked by C-bound methylhydroxyl and [(methoxycarbonyl)amino]phenyl groups.
In the crystal, amide-N—H⋯O(carbonyl) hydrogen bonding [N2—H2n⋯O3i: H2n⋯O3i = 2.083(14) Å, N2n⋯O3i = 2.910(3) Å with angle at H2n = 163(3)° for symmetry operation (i): 1 − x, −1/2 + y, 2 − z] connect molecules into a helical supramolecular chain along the b-axis. The presence of methine-C—H⋯O(amide) [C3—H3⋯O1ii: H3⋯O1ii = 2.60 Å, C3⋯O1ii = 3.294(4) Å with angle at H3 = 132° for (ii) −1 + x, y, z] interactions link the chains into a supramolecular layer in the ab-plane. The layers stack without directional interactions between them. In order to understand more fully the nature of the intermolecular contacts in the crystal, an analysis of the Hirshfeld surfaces along with two-dimensional fingerprint plots was undertaken with the aid of Crystal Explorer 17 [14] and literature protocols [15].
The fingerprint plot delineated into H⋯O/O⋯H contacts showed the distinctive spikes due to the N—H⋯O hydrogen bonds and overall, contributed 24.5% of all contacts, with H⋯H contacts being most dominant, at 57.9%. The next most significant contribution to the calculated surface contacts is from H⋯C/C⋯H contacts [11.6%] with smaller contibutions from N⋯C/C⋯N [2.9%] and H⋯N/N⋯H [2.7%] contacts.
Acknowledgements
The Brazilian agencies Coordination for the Improvement of Higher Education Personnel, CAPES, Finance Code 001 and the National Council for Scientific and Technological Development (CNPq) are acknowledged for grants (312210/2019–1, 433957/2018–2 and 406273/2015–4) to IC and for a fellowship (303207/2017–5) to JZS. Sunway University Sdn Bhd is thanked for financial support of this work through Grant No. STR-RCTR-RCCM-001–2019.
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©2020 Ignez Caracelli et al., published by De Gruyter, Berlin/Boston
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- The crystal structure of oxonium hexaquaaluminium disulfate hexahydrate
- Crystal structure of catena{(μ2-1,10-phenanthroline-κ4N,N,N′,N′)-(μ2-1,10-phenanthroline-κ3N,N,N′)potassium(I) {[bis(2-hydroxyethyl)iminiumyl](sulfanidyl)methyl}sulfanide hemi(1,10-phenanthroline)}, {C24H16KN4, 0.5(C12H8N2), C5H10NO2S2}
- Crystal structure of chlorido-[(N,N-di-isobutyl)dithiocarbamato-κ2S,S′]-di(4-methylbenzyl-κC)tin(IV), C25H36ClNS2Sn
- Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-(4-chloro-4-pyridyl-2,2′:6′,2′′-terpyridine-κ2N,N′) rhodium(III) hexaflourophosphate, C31H29Cl2F6N3PRh
- The crystal structure of catena-poly[bis-(3,5-dinitro-1,2,4-triazolato-κ2N:O)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′)copper(II)], C16H10CuN14O8
- Crystal structure of poly[triaqua-bis(μ3-3,3′-((5-carboxylato-1,3-phenylene)bis(oxy))dibenzoato)-tris(1,10-phenanthroline)cobalt(II)], C78H46N6O20Co3
- The crystal structure of 2,4-dihydroxybenzoic acid–nicotinamide–methanol (1/1/1), C15H18N2O6
- The crystal structure of aqua{N,N,N′,N′-tetrakis[(1H-benzimidazol-κN3) methyl]cyclohexane-1,2-diamine}lead(II) diacetate–methanol (1/2), C44H54N10O7Pb
- Crystal structure of (2-amino-5-bromo-3-iodophenyl)(3-(4-chlorophenyl)oxiran-2-yl)methanone, C15H10BrClINO2
- Synthesis and crystal structure of 3-octyl-5,5-diphenylimidazolidine-2,4-dione, C23H28N2O2
- Synthesis and crystal structure of 2-azido-N-(4-nitrophenyl)acetamide, C8H7N5O3
- Crystal structure of tert-butyl (1S,2R,5R)-2-(hydroxymethyl)-4-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, C17H23NO5
- Crystal structure of 4-[(4-methoxy-2-nitrophenyl)carbamoyl]butanoic acid, C12H14N2O6
- Crystal structure of 3-ethyl-1-[(E)-[(2E)-3-phenylprop-2-en-1-ylidene]amino]thiourea, C12H15N3S
- Crystal structure of 4,4′-bipyridin-1,1′-dium poly[bis(μ4-benzene-1,3,5-triyltris(hydrogen phosphonato-κ4O:O′:O′′:O′′′))zinc(II)], C11H11NO9P3Zn
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)butane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]-di-gold(I), C44H42Au2F2N2O2P2S2
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)hexane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]digold(I), C46H46Au2F2N2O2P2S2
- Crystal structure of tetrakis (N-(2-hydroxyethyl)-N-isopropylcarbamodithioato-κS,S′)-(μ2(2-(pyridin-4-yl)vinyl)pyridine-κN,N′)dicadmium(II), C36H58Cd2N6O4S8
- Crystal structure of 4-(2-(benzo[b]thiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile, C20H12F6N2S
- Crystal structure of bis(octahydrocyclopenta[c]pyrrolium)pentachlorobismuthate(III), (C7NH14)2BiCl5
- The crystal structure of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)samarium(III), C24H36N9O15Sm
- Synthesis and crystal structure of methyl 2-(2-((tert-butoxycarbonyl)amino)phenyl)-2-(4-oxo-4H-chromen-3-yl)acetate, C23H23NO6
- Crystal structure of O-hexyl benzoylcarbamothioate, C14H19NO2S
- Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S
- Crystal structure of chlorido-(O-ethyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)-silver(I), C45H41AgClNOP2S
- Crystal structure of 4-[(2-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
- Crystal structure of ethyl 4-methyl-2-oxo-5-phenyl-1,3,4-oxadiazinane-3-carboxylate, C13H16N2O4
- Crystal structure of catena-poly[diaqua(μ2-2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylato)cadmium(II)], C6H8CdN2O7
- Crystal structure of (1S)-N-(chloromethyl)-1-((4S,6aR,8aS, 8bR,9aR)-4-methoxy-6a,8a-dimethyl-1,3,4, 5,6,6a,6b,7,8,8a,9a,10,10a,10b-tetradecahydro-8bH-naphtho[2′,1′:4,5] indeno[1,2-b]oxiren-8b-yl)-N-methylethan-1-amine, C24H46ClNO5
- Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3
- Crystal structure of (2Z)-2-amino-3-[(E)-[(2,4-dihydroxyphenyl)methylidene]-amino]but-2-enedinitrile, C11H8N4O2
- Crystal structure of 3-methyl-1-[(E)-(4-phenylbutan-2-ylidene)amino]thiourea, C12H17N3S
- Crystal structure of carbonyl{hydridotris[3-phenyl-5-methylpyrazol-1-yl]borato-κ3N,N′N′′}copper(I), C31H28BCuN6O
- Crystal structure of ethane-1,2-diylbis(diphenylphosphine oxide) – dihydrogenperoxide (1/2), C26H28O6P2
- Crystal structure of 2-(pyridin-2-ylamino)pyridinium chloride dibenzyldichlorostannane, [C10H10N3]Cl, C14H14Cl2Sn
- Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
- Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
- Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
- Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
- Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
- Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
- Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
- The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
- Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo
Articles in the same Issue
- Frontmatter
- Crystal structure of poly[tetraaqua-bis(μ4-5-(4-carboxy-benzylamino)-isophthalato-κ4O,O′:O′′:O′′′)-(μ2-4,4′-di(1H-imidazol-1-yl)-1,1′-biphenyl-κ2N:N′)dicadmium(II)], C25H22N3O8Cd
- The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C19H18N2O3
- Crystal structure of poly[aqua-μ2-4,4′-bipyridine-κ2N:N′)-μ2-bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ2O,O′)zinc(II)], C38H28Cl4N4O4Zn
- Crystal structure of 1-(2-(1H-indol-3-yl)ethyl)-4-benzyl-3-hydroxy-3,6-diphenylpiperazine-2,5-dione, C33H29N3O3
- The crystal structure 2,2′-bipyridine-κ2N,N′-(2-(3-amino-4-chlorobenzoyl)benzoato-κ1O)-(2-(3-amino-4-chlorobenzoyl)benzoato-κ2O,O′)zinc(II) — ethanol (1/1), C40H32Cl2N4O7Zn
- Crystal structure of catena-poly[(μ3-2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ3O:O′:O′′)-bis(μ2-4,4′-bis(pyrid-4-yl)biphenyl-k1N)copper(II)], C60H40N4O9Cu
- The crystal structure of dimethylammonium catena-[di(μ-aqua)-bis(μ9-benzene-1,3,5-tricarboxylato)pentalithium], C20H16Li5NO13
- Crystal structure of tetraaqua-bis(3,5-di(pyridin-4-yl)-1,2,4-triazol-1-ido-κ1N)nickel(II) dihydrate, C24H28O6N10Ni
- The crystal structure of tetrakis(1-methylimidazole-κ1N)-oxido-(sulfato-κ1O)vanadium(IV), C16H24N8O5SV
- Crystal structure of methyl 2-(6,11-dioxo-2,3,6,11-tetrahydro-1H-benzo[f]pyrrolo[2,1-a]isoindole-5-carbonyl)benzoate, C24H17NO5
- Crystal structure of (E)-N′-(2-hydroxy-4-(2-(piperidin-1-yl)ethoxy)benzylidene) nicotinohydrazide monohydrate, C20H24N4O3 ⋅ H2O
- Crystal structure of poly[bis(μ3-(1-(3,5-di(1H-imidazol-1-yl)phenyl)-1H-imidazole-κ3N:N′:N′′)cobalt(II)] dinitrate — N,N-dimethylformamide (1/4), C42H52N18O10Co
- The crystal structure bis{hexakis(1-methyl-1H-imidazole-κ1N)cobalt(II)} tetrakis(μ3-oxido)-octakis(μ2-oxido)-tetradecaoxido-octamolybdate(VI), C24H36CoMo4N12O13
- Crystal structure of di-μ-nicotinato-κ2N:O; κ2O:N-bis-[aqua-bis(benzyl)(nicotinato-κ2O,O′)tin(IV)], C52H48N4O10Sn2
- Crystal structure of dichlorido-bis[2-(2-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)phenoxy)benzoic acidmanganese(II) monohydrate, C40H30N8O7MnCl2
- The crystal structure of benzyl 3β-acetylglycyrrhetate, C39H54O5
- Synthesis and crystal structure of (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one, C24H20N2O2
- Crystal structure of trans-dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV) dimethylsulphoxide solvate, C26H22Cl4N2OSSn
- Crystal structure of phenyl(1,3,4a-triphenyl-4a,5,6,10b-tetrahydro-1H-[1,4]oxazino[2,3-c]quinolin-5-yl)methanone, C36H28N2O2
- Crystal structure of (4aS,5S,6aS,6a1S, 10aS)-4a,5,6a,6a1,9,10-hexahydro-7H-4,5-methanocyclobuta[4,5]naphtho[8a,1-b]pyran-6(2H)-one, C15H16O2
- Crystal structure of [(Z)-O-isopropyl N-(4-chlorophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuClNOPS
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-P,P′)-bis[(Z)-O-isopropyl N-(4-chlorophenyl)thiocarbamato-S]-di-gold(I) acetonitrile di-solvate, C54H50Au2Cl2FeN2O2P2S2⋅2(C2H3N)
- Crystal structure of (6aR,6a1S,10aS)-2,4a,6a,6a1,9,10-hexahydro-7H-4,5-methanocyclobuta[4,5]naphtho[8a,1-b]pyran, C15H16O
- Crystal structure of 5,17-diformyl-25,26,27,28-tetrahydroxycalix[4]arene- dichloromethane, C31H26Cl2O6
- Crystal structure of 2-tert-butyl 1-methyl 5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate, C19H24N2O6
- Crystal structure of [2-carboxybenzene-1-thiolato-S]-(triethylphosphane-P)-gold(I), C13H20AuO2PS
- Synthesis and crystal structure of bis(5-methyl-2-aldehyde-phenolato-κ2O1,O2)copper(II), C16H14CuO4
- Crystal structure of poly[triaqua-(di(2,2′-bipyridine-κ2N,N′)-μ4-silanetetrayltetrakis(benzene-4,1-diyl)tetrakis (hydrogen phosphonato)-κ4O:O′:O′′:O′′′) dicadmium(II)], C44H42N4O15P4Cd2Si
- Crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)]-bis(triethylphosphine-P)-di-silver(I), C22H50Ag2N2P2S4
- Crystal structure of bis[μ2-(pyrrolidine-1-carbodithioato-κS:κS,κS′)]-bis(triethylphosphine-κP)disilver(I), C22H46Ag2N2P2S4
- Crystal structure of bis[μ2-(N-(2-hydroxyethyl)-N-methylcarbamodithioato-κS:κS,κS′)]-bis(triethylphosphine-P)-di-silver(I), C20H46Ag2N2O2P2S4
- The crystal structure of (2E,2′E)-,2,2′-bis[1-(2-pyrazinyl)ethylidene]carbonimidic dihydrazide, C13H15N9
- The crystal structure of (E)-1-(quinolin-2-ylmethyl)-2-((1-(quinolin-2-ylmethyl)pyridin-2(1H)-ylidene)amino)pyridin-1-ium, C30H25BrN5
- Crystal structure of catena-poly[(μ2-1-((benzotriazol-1-yl)methyl)-1H-1,3-imdazole-κ2N:N′)-(1-((benzotriazol-1-yl)methyl)-1H-1,3-imdazole-κ1N)-(methanol-κ1O)mercury(II)] dinitrate, C21H22N12O7Hg
- Crystal structure of 1-(6-hydroxy-2-phenylbenzofuran-5-yl)ethan-1-one, C16H12O3
- The crystal structure of oxonium hexaquaaluminium disulfate hexahydrate
- Crystal structure of catena{(μ2-1,10-phenanthroline-κ4N,N,N′,N′)-(μ2-1,10-phenanthroline-κ3N,N,N′)potassium(I) {[bis(2-hydroxyethyl)iminiumyl](sulfanidyl)methyl}sulfanide hemi(1,10-phenanthroline)}, {C24H16KN4, 0.5(C12H8N2), C5H10NO2S2}
- Crystal structure of chlorido-[(N,N-di-isobutyl)dithiocarbamato-κ2S,S′]-di(4-methylbenzyl-κC)tin(IV), C25H36ClNS2Sn
- Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-(4-chloro-4-pyridyl-2,2′:6′,2′′-terpyridine-κ2N,N′) rhodium(III) hexaflourophosphate, C31H29Cl2F6N3PRh
- The crystal structure of catena-poly[bis-(3,5-dinitro-1,2,4-triazolato-κ2N:O)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′)copper(II)], C16H10CuN14O8
- Crystal structure of poly[triaqua-bis(μ3-3,3′-((5-carboxylato-1,3-phenylene)bis(oxy))dibenzoato)-tris(1,10-phenanthroline)cobalt(II)], C78H46N6O20Co3
- The crystal structure of 2,4-dihydroxybenzoic acid–nicotinamide–methanol (1/1/1), C15H18N2O6
- The crystal structure of aqua{N,N,N′,N′-tetrakis[(1H-benzimidazol-κN3) methyl]cyclohexane-1,2-diamine}lead(II) diacetate–methanol (1/2), C44H54N10O7Pb
- Crystal structure of (2-amino-5-bromo-3-iodophenyl)(3-(4-chlorophenyl)oxiran-2-yl)methanone, C15H10BrClINO2
- Synthesis and crystal structure of 3-octyl-5,5-diphenylimidazolidine-2,4-dione, C23H28N2O2
- Synthesis and crystal structure of 2-azido-N-(4-nitrophenyl)acetamide, C8H7N5O3
- Crystal structure of tert-butyl (1S,2R,5R)-2-(hydroxymethyl)-4-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, C17H23NO5
- Crystal structure of 4-[(4-methoxy-2-nitrophenyl)carbamoyl]butanoic acid, C12H14N2O6
- Crystal structure of 3-ethyl-1-[(E)-[(2E)-3-phenylprop-2-en-1-ylidene]amino]thiourea, C12H15N3S
- Crystal structure of 4,4′-bipyridin-1,1′-dium poly[bis(μ4-benzene-1,3,5-triyltris(hydrogen phosphonato-κ4O:O′:O′′:O′′′))zinc(II)], C11H11NO9P3Zn
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)butane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]-di-gold(I), C44H42Au2F2N2O2P2S2
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)hexane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]digold(I), C46H46Au2F2N2O2P2S2
- Crystal structure of tetrakis (N-(2-hydroxyethyl)-N-isopropylcarbamodithioato-κS,S′)-(μ2(2-(pyridin-4-yl)vinyl)pyridine-κN,N′)dicadmium(II), C36H58Cd2N6O4S8
- Crystal structure of 4-(2-(benzo[b]thiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile, C20H12F6N2S
- Crystal structure of bis(octahydrocyclopenta[c]pyrrolium)pentachlorobismuthate(III), (C7NH14)2BiCl5
- The crystal structure of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)samarium(III), C24H36N9O15Sm
- Synthesis and crystal structure of methyl 2-(2-((tert-butoxycarbonyl)amino)phenyl)-2-(4-oxo-4H-chromen-3-yl)acetate, C23H23NO6
- Crystal structure of O-hexyl benzoylcarbamothioate, C14H19NO2S
- Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S
- Crystal structure of chlorido-(O-ethyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)-silver(I), C45H41AgClNOP2S
- Crystal structure of 4-[(2-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
- Crystal structure of ethyl 4-methyl-2-oxo-5-phenyl-1,3,4-oxadiazinane-3-carboxylate, C13H16N2O4
- Crystal structure of catena-poly[diaqua(μ2-2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylato)cadmium(II)], C6H8CdN2O7
- Crystal structure of (1S)-N-(chloromethyl)-1-((4S,6aR,8aS, 8bR,9aR)-4-methoxy-6a,8a-dimethyl-1,3,4, 5,6,6a,6b,7,8,8a,9a,10,10a,10b-tetradecahydro-8bH-naphtho[2′,1′:4,5] indeno[1,2-b]oxiren-8b-yl)-N-methylethan-1-amine, C24H46ClNO5
- Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3
- Crystal structure of (2Z)-2-amino-3-[(E)-[(2,4-dihydroxyphenyl)methylidene]-amino]but-2-enedinitrile, C11H8N4O2
- Crystal structure of 3-methyl-1-[(E)-(4-phenylbutan-2-ylidene)amino]thiourea, C12H17N3S
- Crystal structure of carbonyl{hydridotris[3-phenyl-5-methylpyrazol-1-yl]borato-κ3N,N′N′′}copper(I), C31H28BCuN6O
- Crystal structure of ethane-1,2-diylbis(diphenylphosphine oxide) – dihydrogenperoxide (1/2), C26H28O6P2
- Crystal structure of 2-(pyridin-2-ylamino)pyridinium chloride dibenzyldichlorostannane, [C10H10N3]Cl, C14H14Cl2Sn
- Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
- Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
- Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
- Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
- Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
- Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
- Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
- The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
- Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
- Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo