Home Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
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Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3

  • Wu-Wu Li EMAIL logo , Min-Yan Zheng , Ying Guo , Yan-Ping Jiang , Qiao Wang , Mei Wang , Min-Xiang Ji , Yu-Tao Zhang and Zun-Ting Zhang
Published/Copyright: May 14, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 4

Abstract

C14H13F2N3O3, triclinic, P1̄ (no. 2), a = 9.4486(7) Å, b = 12.4694(8) Å, c = 13.8690(8) Å, α = 65.734(6)°, β = 74.523(5)°, γ = 83.726(6)°, V = 1435.63(18) Å3, Z = 4, Rgt(F) = 0.0495, wRref(F2) = 0.1249, T = 293(2) K.

CCDC no.: 1911889

The molecular 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:Colorless block
Size:0.22 × 0.16 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.12 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:26.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:12806, 5941, 0.032
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4624
N(param)refined:400
Programs:SHELX [1], Bruker [2]
Table 2:

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

AtomxyzUiso*/Ueq
C1−0.0749(2)0.23340(15)0.76413(14)0.0160(4)
C2−0.0381(2)0.12764(16)0.86157(14)0.0168(4)
C3−0.0693(2)0.28591(16)0.90792(14)0.0167(4)
C4−0.0994(2)0.33038(16)0.80553(14)0.0161(4)
C5−0.1429(2)0.44558(16)0.75910(15)0.0200(4)
H5−0.1646110.4751140.6912350.024*
C6−0.1538(2)0.51690(17)0.81634(15)0.0232(4)
H6−0.1825300.5950180.7864370.028*
C7−0.1218(2)0.47161(17)0.91758(16)0.0234(4)
H7−0.1292100.5203750.9545330.028*
C8−0.0788(2)0.35484(16)0.96565(15)0.0202(4)
H8−0.0574260.3248711.0336470.024*
C90.0407(2)0.25558(16)0.65561(14)0.0161(4)
H90.0950630.1827550.6602530.019*
C10−0.0564(2)0.28369(17)0.57617(14)0.0194(4)
H10−0.0650460.3692890.5399610.023*
C11−0.0060(2)0.23396(19)0.49080(16)0.0272(5)
H11−0.0763000.2523590.4454850.033*
C120.1470(2)0.35188(16)0.62703(15)0.0188(4)
C130.3302(2)0.40651(18)0.68647(18)0.0295(5)
H13A0.2764930.4703960.7026700.035*
H13B0.3903710.4386230.6122790.035*
C140.4238(3)0.3456(2)0.7644(2)0.0431(6)
H14A0.4774840.2834340.7467390.065*
H14B0.3628820.3132470.8372820.065*
H14C0.4915210.4008610.7593540.065*
O1−0.01762(15)0.02754(11)0.86557(10)0.0219(3)
O20.15592(16)0.44614(12)0.55093(11)0.0300(4)
O30.22838(14)0.31851(11)0.69918(10)0.0215(3)
N1−0.20270(17)0.23436(14)0.64525(12)0.0202(4)
N2−0.21353(17)0.20732(13)0.74359(12)0.0190(4)
N3−0.03136(17)0.16603(13)0.93806(12)0.0174(3)
H3−0.0069100.1227050.9978560.021*
F10.01448(15)0.11520(11)0.53827(10)0.0388(3)
F20.12883(13)0.27960(11)0.42869(9)0.0346(3)
C1A0.5974(2)0.26070(16)0.21774(14)0.0176(4)
C2A0.5569(2)0.37141(16)0.12584(14)0.0186(4)
C3A0.5867(2)0.22169(16)0.06779(14)0.0183(4)
C4A0.6213(2)0.17050(16)0.16873(14)0.0181(4)
C5A0.6638(2)0.05416(17)0.20900(15)0.0227(4)
H5A0.6880880.0199980.2760170.027*
C6A0.6696(2)−0.01105(18)0.14691(17)0.0266(5)
H6A0.697350−0.0897340.1727460.032*
C7A0.6343(2)0.04077(18)0.04745(17)0.0266(5)
H7A0.638876−0.0039840.0071010.032*
C8A0.5918(2)0.15860(17)0.00542(16)0.0232(4)
H8A0.5679970.192965−0.0617610.028*
C9A0.4808(2)0.23099(16)0.32695(14)0.0177(4)
H9A0.4282620.3026930.3286180.021*
C10A0.5771(2)0.19000(17)0.40784(14)0.0198(4)
H10A0.5857270.1041230.4354130.024*
C11A0.5269(2)0.22515(18)0.50298(16)0.0265(5)
H11A0.5957830.1968590.5500010.032*
C12A0.3732(2)0.14108(16)0.34273(14)0.0184(4)
C13A0.1915(2)0.10870(17)0.26876(18)0.0292(5)
H13C0.1259910.0732840.3406680.035*
H13D0.2434220.0464940.2487190.035*
C14A0.1069(3)0.1820(2)0.1874(2)0.0424(6)
H14D0.1732540.2174530.1169940.064*
H14E0.0551030.2424540.2088460.064*
H14F0.0378800.1333490.1840820.064*
O1A0.53441(15)0.46797(11)0.12974(10)0.0237(3)
O2A0.36167(16)0.04148(12)0.41016(11)0.0289(3)
O3A0.29505(14)0.18741(11)0.26836(10)0.0196(3)
N1A0.72388(18)0.24281(14)0.34234(12)0.0227(4)
N2A0.73507(17)0.28148(13)0.24255(12)0.0204(4)
N3A0.54801(17)0.34044(13)0.04538(12)0.0189(4)
H3A0.5219070.387446−0.0127000.023*
F1A0.51216(15)0.34467(11)0.46668(9)0.0377(3)
F2A0.39011(13)0.18027(11)0.55989(9)0.0320(3)

Source of material

The mixture of CF2HCH2NH2 (1.0 mmol), tBuONO (1.2 mmol), AcOH (0.15 mmol) and DCM (dichloromethane; 20 mL) was stirred at 70 °C for about 10 min. The mixture was placed at room temperature, then was added (E)-ethyl 2-(2-oxoindolin-3-ylidene)acetate (0.3 mmol). The reaction was monitored by thin-layer chromatography (TLC), which showed the disappearance of (E)-ethyl 2-(2-oxoindolin-3-ylidene)acetate that was indicative of the reaction being complete. After DCM was removed under reduced pressure, the residue was purified by column chromatography on silica gel column using petroleum ether/ethyl acetate (6:1, v/v) to give the corresponding pure title compound. Crystals were obtained at room temperature from the mother liquor.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses and placed in geometrically idealized positions. The Uiso values of the hydrogen atoms of methyl groups were set to 1.Ueq(C) and the Uiso values of all other hydrogen atoms were set to 1.Ueq(C).

Comment

1H-Indole-2,3-dione (isatin) and its derivatives exhibit an extraordinary biological activity. It is well known that isatin was found in human organism and its influence on different systems in organism has long been discussed in the literature [3], [4], [5], [6], [7], [8], [9], [10]. The biological activity of isatin includes the impact on human brain and protection from different types of infectious diseases [7], [8], [9]. N-Methylisatin-3-thiosemicarbazone (methisazon) is one of the first antivirals used in clinical practice. In recent years, isatin derivatives with acylhydrazone substituents at the C(3) position of the indole cycle have been intensively studied as antituberculosis drugs [10]. N-Alkyl-substituted isatins can act as selective antagonists of cannabinoid receptor 2 in treating neuropathic pain [11]. On the other hand pyrazole derivatives have known to exhibit diverse biological applications such as antidiabetic [12], anaesthetic [13], antimicrobial and antioxidant [14]. According to physiological activity structure combination strategy, indolin-2-one skeleton and 4,5-dihydro-3H-pyrazole ring were joined together and the title compound was synthesized.

The molecular structure of the title structure consists of one indolin-2-one ring, a 4,5-dihydro-3H-pyrazole ring, a difluoromethyl and a ethyl formate group (cf. the figure). The title structure contains two crystallographically independent molecules Mole1 (C1—C14/N1–N3/O1—O3) and Mole2 (C1A—C14A/N1A—N3A/O1A—O3A), Mole1 and Mole2 are a pair of optical isomers. Furthermore the space group symmetry verifies the inverted molecules additionally. The indolin-2-one ring is essentially planar, with a mean deviation from plane of 0.0152(2) Å for Mole1 and 0.0168(2) Å for Mole2. The 4,5-dihydro-3H-pyrazole ring adopts an envelope conformation with C9 atom deviating by 0.3474(3) Å from the plane formed by C1, C10, N1 and N2 for Mole1, C9A atom deviats by 0.3816(2) Å from the plane formed by C1A, C10A, N1A and N2A for Mole2 [15]. The bond lengths and angles of indolin-2-one and 4,5-dihydro-1H-pyrazole ring are similar to those found in literature [16], [17], [18]. The indolin-2-one ring and 4,5-dihydro-3H-pyrazole ring form spiro structural feature through their third atom (C1). Because C1 is a sp3 hybridized carbon, the indolin-2-one ring is non-coplanar with 4,5-dihydro-3H-pyrazole ring, the dihedral angles between the two rings are 89.793(4)° for Mole1 and 89.471(2)° for Mole2. In the crystal structure of title compound, adjacent molecules are connected by classical hydrogen bonds N3(A)—H3(A)⋯O1(A) and C10(A)—H10(A)⋯O2(A) to form one-dimensional chain along the direction [011].

Acknowledgements

This research was supported by Scientific Research Program Funded by Shaanxi Provincial Education Department (No. 18 J K0837 and 16 J K1822), Natural Science Basic Research Plan Funded by Shaanxi Province of China (No. 2018JM2045 and 2016JM5024), Science and Technology Projects of Xianyang City (No. 2017k02–19), Scientific Research Project Funded by Xianyang Normal University (No. XSYK18006), Youth Backbone Teachers Project Funded by Xianyang Normal University (No. XSYGG201606), University Students Research and Innovation Training Program of Ministry of Education (201810722010), University Students Research and Innovation Training Program of Shaanxi Province (No. 201828010 and 2490), University Students Research and Innovation Training Program of Xianyang Normal University (No. 2018003, 2017060 and 201710722003), and Scientific Research Project Funded by Ministry of Land Resources (No. SXDJ2017–3). The corresponding author confirms explicitly that all listed authors significantly contributed to this work.

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Received: 2019-03-13
Accepted: 2019-04-24
Published Online: 2019-05-14
Published in Print: 2019-06-26

© 2019 Wu-Wu Li 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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  41. Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
  42. Redetermination of the crystal structure of bis(μ2-di-ethyldithiocarbamato-κ3S,S′:S;κ3S:S: S′)-hexacarbonyl-di-rhenium(I), C16H20N2O6Re2S4
  43. The crystal structure of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide, C19H16O2N2
  44. Crystal structure of 6-hydroxy-4,8,11b-trimethyltetradecayhdro-8,11-epoxy-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid – methanol (1/1), C20H30O4
  45. The crystal structure of aqua-bis(3-acetyl-2-oxo-2H-chromen-4-olato-κ2O,O′)zinc(II) monohydrate, C22H18O10Zn
  46. Crystal structure of poly[bis(μ2-4-bromoisophthalate-κ2O:O′)-tris(μ2-1-(3-((1H-1,2,4-triazol-1-yl)methyl)benzyl)-1H-1,2,4-triazole-κ2N:N′)dicobalt(II)] monohydrate, C26H23CoN9O5Br
  47. A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2
  48. Crystal structure of catena-poly[diaqua-bis(μ2-4-((4-(pyridin-2-ylmethoxy)phenyl)diazenyl)benzoato-κ3O,O′:N)cadmium(III)], Cd(C19H14O3N3)2(H2O)
  49. Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
  50. Crystal structure of 3-amino-2-hydroxy-6-methoxybenzamide hydrate, C16H22N4O7
  51. Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]
  52. Crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-(thiophen-2-yl)-1,3,5-triazine, C10H6ClN3OS
  53. The crystal structure of 3-butyl-1-methyl-1H-imidazol-3-ium catena-poly[tris(μ2-bromido-κ2Br:Br)lead(II)], C8H15Br3N2Pb
  54. Crystal structure of 3-(5-amino-1H-1,2,4-triazol-3-yl)-1-(piperidin-1-yl)propan-1-one, C10H17N5O
  55. Crystal structure of aqua-2,2′,2′′-(((nitrilo-κN-tris(ethane-2,1-diyl))tris(azanylylidene-κ3N′,N′′,N′′′))tris(methanylylidene))tris(4-chlorophenolato-κ3O,O′,O′′)neodymium(III), C27H26Cl3N4NdO4
  56. Crystal structure of dichlorido-(μ2-2,2′-(diazene-1,2-diyl)bis(benzen-1-ido)-κ2C:C′)dimercury(II), C12H8Cl2Hg2N2
  57. Crystal structure of (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C27H18FN3O3S
  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
https://doi.org/10.1515/ncrs-2019-0188
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-5-fluorophenol, C14H13FN2O
  3. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4,6-dichlorophenol, C14H12Cl2N2O
  4. The crystal structure of (E)-1-(4-methoxyphenyl)-3-(2-nitrophenyl)triaz-1-ene C8H8N2O4
  5. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one—methanol (1:1), C32H30N5O2Br ⋅ CH4O
  6. Crystal structure of 2,4-pentanedione bis(2,4-dinitrophenylhydrazone), C17H16N8O8
  7. Crystal structure of sodium morpholine-4-carbodithioate, (C5H12NNaO3S2)
  8. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorido phosphate), C16H28F12N4P2
  9. Crystal structure of 5-(4-chlorophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C21H16ClFN2
  10. Crystal structure of catena-poly[diaqua-bis(3-carboxy-5-methoxybenzoato-κO)-(1,2-bis(imidazol-1-yl)ethane-κ2N:N′)cobalt(II)], C26H28CoN4O12, [Co(C9H6O5)2(H2O)2(C8H10N4)]
  11. The crystal structure of 3-cyclohexyl-1,5-dioxaspiro[5.5]undecane-2,4-dione, C15H22O4
  12. Crystal structure of (2,4-dimethoxybenzyl)triphenylphosphonium trifluoroacetate — trifluoroacetic acid (1/1), C31H27F6O6P
  13. Crystal structure of 4-tert-butyl-1-(2,6-dimethylphenyl)-1H-1,2,3-triazole, C14H19N3
  14. Crystal structure of 1,1′-methylenebis(4-tert-butylpyridinium) tetrachloridocobaltate(II) – dichloromethane (1:1), C20H30Cl6CoN2
  15. Crystal structure of (4,4′-(ethane-1,2-diylbis((nitrilo)(2-furylmethylylidene)))bis(3-methyl-1-phenyl-1H-pyrazol-5-olato-κ4N,N′,O,O′))-nickel(II)), C32H26N6NiO4
  16. Synthesis and crystal structure of bis{((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ2N,O}copper(II), C44H38CuN4O4
  17. Crystal structure of catena-poly[diaqua-bis(3,5-dichloropyridine-4-carboxylato-κ1O)-bis(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C22H16Cl4CoN4O6
  18. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3,5-dinitrophenyl)diazene 1-oxide, C12H4Cl2N6O9
  19. The crystal structure of 3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydroquinolin — dimethylsulfoxide (1/1), C21H19ClFN3O2S
  20. The crystal structure of dichlorido-bis(1-butyl-1H-imidazole-κN)zinc(II), C14H24Cl2ZnN4
  21. (Z)-N-tert-butyl-1-(2-(3,5-dichlorobenzamido)phenyl) methanimine oxide, C18H18Cl2N2O2
  22. Crystal structure of diaqua-bis(3-carboxy-5-bromoisophthalato-κO)-bis(1-(3-(1H-benzo[d]imidazol-1-yl)propyl)-1H-benzo[d]imidazol-3-ium-κN)nickel(II) bis(3-carboxy-5-bromoisophthalate), C66H54Br4N8NiO18
  23. Crystal structure of poly[aqua(μ2-5-methoxyisophthalato-κ2O,O′:O′′)-(1,2-bis(imidazol-1′-yl)ethane-κ2N:N′)cobalt(II), C34H36Co2N8O12
  24. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)] terephthalate tetrahydrate, MnC32H38N10O10
  25. Crystal structure of the fluorescent fipronil derivative 5,5′-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile), C25H6N8O2Cl4F12S2
  26. Crystal structure of the phosphorescent complex diethyldithiophosphonato-κ2S,S′-bis(2-phenylpyridinato-κ2C,N)iridium(III), C26H26N2O2PS2Ir
  27. The crystal structure of 4,10-diethoxy-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine, C18H18O5
  28. Crystal structure of dichlorido-bis(N-benzyl-2-(quinolin-8-yloxy)acetamide-κ2N,O)copper(II) — ethyl acetate (1/1), C38H36N4O6Cl2Cu
  29. Synthesis and crystal structure of bis{4-methyl-2-((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)phenolato-κ3N,O,O}copper(II), C92H84Cu2N8O8
  30. The crystal structure of 1,3,5-trinitro-4,6-diazidobenzene, C6HN9O6
  31. Crystal structure 1-cinnamyl-2-((Z)-styryl)-1H-benzo[d]imidazole — methanol (1/1), C24H20N2 ⋅ CH4O
  32. The crystal structure of poly[m2-aqua-tetraaqua-bis(m9-4-formylbenzene-1,3-disulfonato)tetrasodium(I) hydrate, C14H18O19S4Na4
  33. Crystal structure of 2-((2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium trifluoroacetate, [C17H17F6N2O][C2F3O2]
  34. The crystal structure of bis(ferrocenecarboxylato-κ2O,O′)bis[4-(dimethylamino)pyridine-κN]copper(II) — acetonitrile(1/2), C40H44CuO4Fe2N6
  35. Crystal structure of poly[di-μ2-aqua)-diaqua-bis(μ6-4,4′,4′′-(benzene-1,3,5-triyltris(oxy))tribenzoato-κ6O1:O2:O3:O3:O5:O6)tricadmium(II)] dihydrate, C54H42Cd3O24
  36. The crystal structure of dichlorido(1,3-bis(2,6-diisopropyl-phenyl)-1H-3λ4-imidazol-2-yl)(3-phenyl-pyridine-κN)palladium(IV), C38H45N3Cl2Pd
  37. The crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-phenyl-1,3,5-triazine, C12H8ClN3O
  38. The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S
  39. Crystal structure of bis{μ2-bis{(((((1-methoxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ3N,O:O}copper(II)}, C68H68Cu2N8O8
  40. Crystal structure of catena-poly[tetraaqua-bis(μ2-2-(4-carboxylatophenoxy)benzoato-κ2O:O′)-pentakis(pyridine-κ1N)dinickel(II)], C53H47N5Ni2O13
  41. Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
  42. Redetermination of the crystal structure of bis(μ2-di-ethyldithiocarbamato-κ3S,S′:S;κ3S:S: S′)-hexacarbonyl-di-rhenium(I), C16H20N2O6Re2S4
  43. The crystal structure of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide, C19H16O2N2
  44. Crystal structure of 6-hydroxy-4,8,11b-trimethyltetradecayhdro-8,11-epoxy-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid – methanol (1/1), C20H30O4
  45. The crystal structure of aqua-bis(3-acetyl-2-oxo-2H-chromen-4-olato-κ2O,O′)zinc(II) monohydrate, C22H18O10Zn
  46. Crystal structure of poly[bis(μ2-4-bromoisophthalate-κ2O:O′)-tris(μ2-1-(3-((1H-1,2,4-triazol-1-yl)methyl)benzyl)-1H-1,2,4-triazole-κ2N:N′)dicobalt(II)] monohydrate, C26H23CoN9O5Br
  47. A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2
  48. Crystal structure of catena-poly[diaqua-bis(μ2-4-((4-(pyridin-2-ylmethoxy)phenyl)diazenyl)benzoato-κ3O,O′:N)cadmium(III)], Cd(C19H14O3N3)2(H2O)
  49. Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
  50. Crystal structure of 3-amino-2-hydroxy-6-methoxybenzamide hydrate, C16H22N4O7
  51. Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]
  52. Crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-(thiophen-2-yl)-1,3,5-triazine, C10H6ClN3OS
  53. The crystal structure of 3-butyl-1-methyl-1H-imidazol-3-ium catena-poly[tris(μ2-bromido-κ2Br:Br)lead(II)], C8H15Br3N2Pb
  54. Crystal structure of 3-(5-amino-1H-1,2,4-triazol-3-yl)-1-(piperidin-1-yl)propan-1-one, C10H17N5O
  55. Crystal structure of aqua-2,2′,2′′-(((nitrilo-κN-tris(ethane-2,1-diyl))tris(azanylylidene-κ3N′,N′′,N′′′))tris(methanylylidene))tris(4-chlorophenolato-κ3O,O′,O′′)neodymium(III), C27H26Cl3N4NdO4
  56. Crystal structure of dichlorido-(μ2-2,2′-(diazene-1,2-diyl)bis(benzen-1-ido)-κ2C:C′)dimercury(II), C12H8Cl2Hg2N2
  57. Crystal structure of (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C27H18FN3O3S
  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
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