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Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4

  • Fatin Nur Ain Abdul Rashid , Mohd Fazli Mohammat EMAIL logo , Suhana Arshad , Zurina Shaameri and Ahmad Sazali Hamzah
Published/Copyright: September 9, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 6

Abstract

C15H17N3O4, triclinic, P1̄ (no. 2), a = 10.5986(5) Å, b = 11.5298(5) Å, c = 13.5386(6) Å, α = 102.694(1)°, β = 102.999(1)°, γ = 108.918(1)°, V = 1446.03(11) Å3, Z = 4, Rgt(F) = 0.0525, wRref(F2) = 0.1526, T = 100(1) K.

CCDC no.: 1479039

Table 1:

Data collection and handling.

Crystal:Orange block
Size:0.24 × 0.21 × 0.13 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:Bruker SMART APEX-II Duo, φ and ω
θmax, completeness:33.4°, 99%
N(hkl)measured, N(hkl)unique, Rint:73858, 11136, 0.050
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 7872
N(param)refined:419
Programs:Bruker [1], SHELX [2], Spek [3], Mercury [4]

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 2:

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

AtomxyzUiso*/Ueq
N1A0.65213(11)0.41861(11)0.48761(8)0.0208(2)
N2A0.75650(10)0.41828(10)0.56589(8)0.0208(2)
N3A0.27976(11)0.23705(11)0.36196(8)0.0216(2)
O1A0.43652(10)0.39827(10)0.33063(8)0.0338(2)
O2A0.31426(9)0.10495(9)0.50149(7)0.02256(18)
O3A0.48760(9)0.10627(9)0.63086(7)0.02215(18)
O4A1.05834(9)0.24363(8)0.93112(7)0.02120(18)
C1A0.52645(12)0.32543(11)0.46876(9)0.0176(2)
C2A0.54855(12)0.25726(11)0.54094(9)0.0172(2)
C3A0.69571(12)0.32016(11)0.59972(9)0.0177(2)
C4A0.78790(12)0.29839(11)0.68710(9)0.0175(2)
C5A0.78258(12)0.17554(11)0.68716(9)0.0181(2)
H5AA0.71440.10150.63050.022*
C6A0.87491(12)0.16028(11)0.76840(9)0.0179(2)
H6AA0.87000.07620.76710.022*
C7A0.97529(11)0.26827(11)0.85228(9)0.0172(2)
C8A0.98506(12)0.39121(11)0.85215(9)0.0200(2)
H8AA1.05510.46530.90780.024*
C9A0.89131(12)0.40509(12)0.76965(9)0.0201(2)
H9AA0.89820.48940.76980.024*
C10A0.40860(12)0.32193(12)0.38133(9)0.0202(2)
C11A0.15894(13)0.23705(14)0.28471(11)0.0267(3)
H11A0.07460.16200.27500.040*
H11B0.17640.23260.21620.040*
H11C0.14480.31660.31120.040*
C12A0.43929(12)0.15065(11)0.55421(9)0.0173(2)
C13A0.38507(12)−0.00275(12)0.64493(9)0.0204(2)
H13A0.3485−0.07960.58060.024*
H13B0.30500.01810.65670.024*
C14A0.45907(15)−0.02924(14)0.74070(11)0.0292(3)
H14A0.3922−0.10100.75390.044*
H14B0.49690.04820.80340.044*
H14C0.5363−0.05220.72720.044*
C15A1.17205(13)0.35331(12)1.01190(10)0.0231(2)
H15A1.22580.32371.06230.035*
H15B1.13400.40911.05020.035*
H15C1.23400.40200.97830.035*
N1B0.54141(10)0.59549(10)0.25371(8)0.01830(19)
N2B0.44011(10)0.58408(10)0.16723(8)0.01920(19)
N3B0.90511(10)0.80346(11)0.38993(8)0.0207(2)
O1B0.76239(9)0.62764(9)0.41632(7)0.02308(19)
O2B0.86270(9)0.92868(9)0.24178(7)0.02146(18)
O3B0.70762(9)0.86463(8)0.07794(7)0.02111(18)
O4B0.12929(9)0.68998(9)−0.23482(7)0.02364(19)
C1B0.66734(12)0.68711(11)0.27008(9)0.0166(2)
C2B0.64854(11)0.74108(11)0.18698(9)0.0165(2)
C3B0.50377(12)0.67138(11)0.12482(9)0.0171(2)
C4B0.41443(12)0.68267(11)0.02924(9)0.0176(2)
C5B0.43412(12)0.65344(12)−0.07021(9)0.0206(2)
H5BA0.51220.6325−0.07640.025*
C6B0.34120(13)0.65437(12)−0.16076(9)0.0214(2)
H6BA0.35530.6334−0.22820.026*
C7B0.22768(12)0.68630(11)−0.15148(9)0.0189(2)
C8B0.20752(12)0.71718(11)−0.05218(9)0.0188(2)
H8BA0.13070.7402−0.04570.023*
C9B0.29956(12)0.71424(11)0.03684(9)0.0184(2)
H9BA0.28440.73390.10400.022*
C10B0.78378(12)0.70430(11)0.36456(9)0.0176(2)
C11B1.02207(13)0.83072(14)0.48354(10)0.0279(3)
H11D1.09940.91130.49280.042*
H11E1.05430.75960.47410.042*
H11F0.99140.83960.54690.042*
C12B0.75130(12)0.85248(11)0.17349(9)0.0172(2)
C13B0.80215(14)0.97189(13)0.05564(10)0.0249(3)
H13C0.89430.96520.06220.030*
H13D0.81761.05550.10600.030*
C14B0.73009(18)0.96135(15)−0.05726(11)0.0345(3)
H14D0.79081.0294−0.07800.052*
H14E0.64070.9712−0.06170.052*
H14F0.71180.8766−0.10560.052*
C15B0.12541(14)0.63066(14)−0.34055(10)0.0274(3)
H15D0.04050.6245−0.39250.041*
H15E0.12400.5438−0.34740.041*
H15F0.20900.6830−0.35430.041*
H1NB0.5194(16)0.5392(16)0.2904(12)0.024(4)*
H1NA0.6678(18)0.4786(17)0.4517(14)0.035(5)*
H3NB0.9094(19)0.8547(18)0.3466(14)0.038(5)*
H3NA0.270(2)0.1825(19)0.4080(15)0.046(5)*

Source of material

Hydrazine hydrate (3.3 mmol) was added to a mixture of ethyl 4-hydroxy-2-(4-methoxyphenyl)-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate (3 mmol) and 15 mL of acetic acid. The mixture was refluxed for 3 h and cooled. The reaction mixture was evaporated under reduced pressure and the crude was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 80/20) to afford the product [5].

Experimental details

Data collection was performed by using the APEX2 software [1] and the cell refinement and data reduction were performed under the SAINT software [1]. The crystal structure was solved by direct method [2] and refined by full-matrix least squares technique on F2 using SHELXTL [2]. Absorption correction was applied to the final crystal data by using the SADABS software [1]. All geometrical calculations were carried out using the program PLATON [2]. The molecular graphics were drawn using SHELXTL [2] and Mercury [4] program. In this compound, the N-bound H atoms were located in difference Fourier maps and allowed to be refined freely [refined distance: N—H = 0.904(16)−0.976(19) Å]. The remaining hydrogen atoms were positioned geometrically [C—H = 0.95−0.99 Å] and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(methyl C). A rotating-group model was used for the methyl groups.

Comment

Pyrazoles play a vital role in pharmaceuticals, since they possess an interesting pharmacological profile, such as anti-inflammatory [6], antimicrobial [7], antiviral [8], antitumor [9], anticonvulsant [10], antidepressant activities [11] and antihistaminic [12] etc. It commonly synthesized either by condensation of hydrazines with 1,3-dicarbonyl or by intermolecular cycloaddition reaction of alkynes to 3-dipoles [13]. During the course of our study, we have unexpectedly found that substituted pyrazole could be synthesized by condensation of pyrrolidine with hydrazine in acidic condition. To the best of our knowledge; this is the first report that synthesizes substituted pyrazole from pyrrolidine ring transformation.

The asymmetric unit of the title compound consists of two crystallographically independent molecules, A and B (left part of the figure). The bond lengths and angles are within the normal ranges and comparable to the related structures [14], [15], [16], [17]. In each molecule (A and B), intramolecular N3A—H3NA⋯O2A and N3B—H3NB⋯O2B hydrogen bond are found, respectively, forming S(7) ring motif [18]. This interaction further stabilizes the molecular structure and locks its atoms in a nearly planar arrangement. In the independent molecule A, the 1-methoxy-4-methylbenzene (C4A—C9A/O4A/C15A) moiety is slightly twisted at C3A—C4A bond with C2A—C3A—C4A—C5A torsion angle of 44.46(19)°. Meanwhile, in molecule B the 1-methoxy-4-methylbenzene (C4B—C9B/O4B/C15B) and ethyl acetate (O2B/O3B/C12B—C14B) moieties are observed to be slightly twisted at C3B—C4B and C2B—C12B bonds, respectively. The twisted angle of C2B—C3B—C4B—C5B is found to be 67.48(18)° while the twisted angle for C1B—C2B—C12B—O2B is −12.4(2)° (right part of the figure). In both molecules, the pyrazole rings (N1A/N2A/C1A—C3A and N1B/N2B/C1B—C3B) form dihedral angles of 41.72(7)° and 62.81(7)° with the phenyl rings (C4A—C9A and C4B—C9B), respectively.

Acknowledgements

The authors would like to acknowledge Universiti Teknologi MARA and Malaysian Government (MOHE) for the financial support (600-IRMI/FRGS 5/3 (0071/2016).

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Received: 2019-03-19
Accepted: 2019-04-29
Published Online: 2019-09-09
Published in Print: 2019-11-26

©2019 Fatin Nur Ain Abdul Rashid et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0203
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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