Home Crystal structure of N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)benzamide, C21H17N3O4S
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Crystal structure of N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)benzamide, C21H17N3O4S

  • Wen-Bo Yu , Jun Xu and Peng-fei Zhang EMAIL logo
Published/Copyright: August 18, 2016
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 231 Issue 4

Abstract

C21H17N3O4S, triclinic, P1̅ (no. 2), a = 10.0424(5) Å, b = 10.4142(4) Å, c = 18.7420(10) Å, α = 91.746(4)°, β = 90.169(4)°, γ = 100.878(4), V = 1923.92(16) Å3, Z = 4, Rgt(F) = 0.0487, wRref(F2) = 0.1036, T = 293(2) K.

CCDC no.:: 1041994

One of two crystallographically independent molecules of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless blocks Size 0.27 × 0.24 × 0.22 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.0 cm−1
Diffractometer, scan mode:Bruker SMART, φ and ω
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:11709, 6767, 0.032
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4900
N(param)refined:528
Programs:Bruker programs [9], SHELX [10], WinGX [11]
Table 2

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

AtomxyzUiso*/Ueq
S10.66013(6)0.31117(7)0.19793(4)0.0544(2)
S20.20429(8)0.43571(7)0.33721(4)0.0639(2)
C120.7002(2)0.1265(2)0.09191(12)0.0426(6)
N20.7400(2)−0.02481(19)−0.00423(11)0.0517(5)
N10.94117(19)0.13877(19)−0.05679(11)0.0532(6)
H10.90750.0597−0.07050.064*
N4−0.0778(2)0.7903(2)0.51076(11)0.0539(6)
H4−0.03080.82490.54720.065*
C330.1870(3)0.6078(2)0.45395(14)0.0498(6)
O11.10377(18)0.31174(17)−0.08315(10)0.0643(5)
O40.28534(18)0.30289(19)0.14072(11)0.0661(5)
O20.63560(19)0.2121(2)0.24991(10)0.0687(5)
O80.4769(2)0.6768(2)0.23621(12)0.0753(6)
C110.7420(2)0.2549(2)0.12300(13)0.0484(6)
C11.0813(2)0.1225(2)−0.15968(13)0.0437(6)
C71.0462(2)0.2004(2)−0.09669(13)0.0452(6)
C80.8808(2)0.1853(2)0.00276(13)0.0466(6)
O30.73535(18)0.43833(19)0.21847(10)0.0724(6)
C29−0.0189(2)0.7031(2)0.46975(13)0.0488(6)
C22−0.2283(2)0.9286(2)0.55588(13)0.0496(6)
C340.1141(2)0.6911(2)0.49211(13)0.0470(6)
C190.5034(2)0.3301(2)0.16489(13)0.0451(6)
C400.3035(2)0.5449(2)0.28174(13)0.0452(6)
C61.0361(2)−0.0114(2)−0.16950(14)0.0526(7)
H60.9816−0.0578−0.13530.063*
C320.1226(3)0.5363(2)0.39316(14)0.0529(7)
C200.4798(3)0.4251(2)0.11688(14)0.0523(7)
C130.7700(2)0.0938(2)0.03066(13)0.0429(6)
N50.1648(2)0.7635(2)0.55103(11)0.0566(6)
C30−0.0781(3)0.6301(3)0.41218(14)0.0571(7)
H30−0.16590.63520.39820.069*
O5−0.2767(2)0.7866(2)0.45369(11)0.0851(7)
C410.4403(3)0.5925(3)0.28755(14)0.0529(7)
C180.3783(3)0.2572(3)0.17838(15)0.0528(7)
C160.5974(2)0.0276(2)0.11694(14)0.0530(7)
H160.54910.04300.15760.064*
C27−0.1364(3)0.9934(3)0.60588(15)0.0596(7)
H27−0.04870.97650.60700.071*
C31−0.0060(3)0.5474(3)0.37427(15)0.0618(8)
H31−0.04720.49860.33510.074*
N30.3511(2)0.4104(2)0.10112(12)0.0599(6)
C28−0.1982(3)0.8294(3)0.50217(14)0.0547(7)
C90.9181(3)0.3065(3)0.03500(15)0.0600(8)
H90.99090.36590.01760.072*
C100.8461(2)0.3405(3)0.09439(15)0.0598(8)
H100.87010.42420.11490.072*
O70.2943(2)0.37312(19)0.37874(13)0.0887(7)
C21.1625(3)0.1883(3)−0.21138(15)0.0623(8)
H21.19390.2779−0.20570.075*
C150.5687(3)−0.0903(3)0.08175(16)0.0630(8)
H150.5006−0.15590.09800.076*
O60.1022(2)0.3571(2)0.29334(13)0.0963(8)
C390.2612(3)0.6063(3)0.22230(15)0.0604(7)
N60.3611(3)0.6853(2)0.19421(13)0.0681(7)
C170.3261(3)0.1462(3)0.22421(18)0.0755(9)
H17A0.24460.16080.24710.113*
H17B0.39300.13890.25980.113*
H17C0.30680.06690.19550.113*
C25−0.3010(4)1.1083(3)0.65313(18)0.0744(9)
H25−0.32591.16770.68620.089*
C350.3174(3)0.6028(3)0.48095(16)0.0638(8)
H350.36920.54850.45850.077*
C140.6419(3)−0.1120(3)0.02122(15)0.0626(8)
H140.6201−0.1930−0.00250.075*
C41.1525(3)−0.0089(3)−0.28030(16)0.0693(9)
H4A1.1766−0.0528−0.32080.083*
C370.2869(3)0.7549(3)0.57283(16)0.0696(8)
H370.32200.80410.61320.084*
C360.3673(3)0.6762(3)0.53897(17)0.0727(9)
H360.45390.67440.55610.087*
C24−0.3927(3)1.0465(3)0.60329(19)0.0836(10)
H24−0.47981.06480.60210.100*
C23−0.3570(3)0.9575(3)0.55495(17)0.0726(9)
H23−0.42020.91620.52120.087*
C51.0719(3)−0.0763(3)−0.22995(17)0.0654(8)
H51.0410−0.1659−0.23630.078*
C26−0.1730(3)1.0825(3)0.65408(17)0.0696(8)
H26−0.11001.12530.68750.084*
C210.5767(3)0.5339(3)0.08490(16)0.0733(9)
H21A0.52720.58820.05910.110*
H21B0.63590.49840.05290.110*
H21C0.62950.58520.12210.110*
C31.1976(3)0.1228(3)−0.27126(16)0.0743(9)
H31.25210.1684−0.30570.089*
C420.5502(3)0.5697(4)0.33553(17)0.0815(10)
H42A0.63160.57110.30860.122*
H42B0.52420.48600.35680.122*
H42C0.56610.63700.37230.122*
C380.1249(3)0.5902(4)0.1879(2)0.1038(13)
H38A0.06600.63010.21800.156*
H38B0.08770.49870.18090.156*
H38C0.13310.63130.14260.156*

Source of material

To a 25 mL schlenk tube charged with CuI and Na2CO3 in 1,4-dioxane was added a mixture of N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)benzamide and 3,5-dimethylisoxazole-4-sulfonyl chloride. The mixture was stirred at 70 °C under a nitrogen atmosphere for 12 h. After cooling to room temperature, the mixture was poured into water (10 mL). Then the mixture was extracted with ethyl acetate for three times, and the combined organic layers were gradually washed with brine (10 mL), dried with Na2SO4, and filtered through a pad of Celite. The solvent was removed under reduced pressure. The residue was then purified by silica-gel column chromatography using petrolether/EtOAc as the eluent to afford a white solid in 82% yield. The solid was recrystallized from CH2Cl2 and Et2O. The resulting solid was filtered off and recrystallized from ethanol to give the pure title compound.

Experimental details

All H atoms were positioned geometrically (C—H = 0.93 or 0.96 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C, N) and 1.5Ueq(Cmethyl).

Discussion

Heteroaromatic sulfones are important organic intermediates and play a vital role in many fields such as pharmacy, and biology [1, 2]. Antimicrobial activity and antioxidant activity of arylsulfonyl isoxazoles have been reported [3, 4]. The traditional synthesis route of heteroaromatic sulfones is the oxidation of the organic sulfides formed via nucleophilic substitution reactions between heteroaryl halides with thiols, which are often not environmentally friendly [5, 6]. Our group has a longstanding interest in C—S cross-coupling reactions [7], and we have developed a copper-based catalytic approach for highly regioselective C—H sulfonylation of 8-aminoquinolines at the C5 position [8]. As a continuation of this work, a arylsulfonyl isoxazole, N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)benzamide was synthesized from N-(quinolin-8-yl)benzamide and 3,5-dimethylisoxazole-4-sulfonyl chloride in the presence of CuI and Na2CO3. To verify the active position of 8-aminoquinoline for this reaction, the structure of title compound was determined. The title structure crystallizes with two molecules in the asymmetric unit. In the structure, the plane C18/C19/C20/N3/O4 and plane C39/C40/C41/N6/O8 make dideral angles of 86.63(7)° and 82.60(6)° with the plane C8/C9/C10/C11/C12 C13/C14/C15/C16 and plane C29/C30/C31/C32/C33/C34/C35/C36/C37 respectively, which both indicate chair conformation. The angle of C11—S1—C19 and angle C 32—S2—C40 are similar within 104.01(1) Å and 104.17(11) Å respectively. In the crystal, two organic molecules are linked at least by a weak C42—H42A⋯O3 hydrogen bond, and are further stablized by other weak N—H⋯N, C—H⋯O hydrogen bonds.

Acknowledgements:

The authors gratefully acknowledge the support from Zhejiang Provincial Natural Science Foundation of China (No. LZ13B020001).

The authors thank the responsible editor for providing the figure.

References

1. Ivachtchenko, A. V.; Golovina, E. S.; Kadieva, M. G.; Kysil, V. M.; Mitkin, O. D.; Tkachenko, S. E.; Okun, I. M.: Synthesis and structure–activity relationship (SAR) of (5,7-disubstituted 3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methylamines as potent serotonin 5-HT6 receptor (5-HT6 R) antagonists. J. Med. Chem. 54 (2011) 8161–8173.10.1021/jm201079gSearch in Google Scholar PubMed

2. Lu, Q.; Zhang, J.; Wei, F.; Qi, Y.; Wang, H.; Liu, Z.; Lei, A.: Aerobic oxysulfonylation of Alkenes Leading to Secondary and Tertiary β-Hydroxysulfones. Angew. Chem. Int. Ed. 52 (2013) 7156–7159.10.1002/anie.201301634Search in Google Scholar PubMed

3. Lavanya, G.; Mallikarjuna, R. L.; Padmavathi, V.; Padmaja, A.: Synthesis and antimicrobial activity of (1,4-phenylene)bis(arylsulfonylpyrazoles and isoxazoles). Eur. J. Med. Chem. 73 (2014) 187–194.10.1016/j.ejmech.2013.11.041Search in Google Scholar PubMed

4. Padmaja, A.; Rajasekhar, C.; Durgamma, S.; Venkatesh, B. C.; Padmavathi, V.: Synthesis and antioxidant activity of pyrazolyl-oxazolines/thiazolines and isoxazolyl-oxazolines/thiazolines. Med. Chem. Res. 23 (2014) 1084–1098.10.1007/s00044-013-0688-zSearch in Google Scholar

5. Trankle, W. G.; Kopach, M. E.: Green chemical synthesis of 2-benzenesulfonyl-pyridine and related derivatives. Org. Process Res. Dev. 11 (2007) 913–917.10.1021/op700060eSearch in Google Scholar

6. Lee, B. S.; Chiou, C. B.: The use of CFC-12, CFC-11 and CH3CCl3 to trace terrestrial airborne pollutant transport by land-sea breezes. Atmos. Environ. 41 (2007) 3360–3372.10.1016/j.atmosenv.2006.12.025Search in Google Scholar

7. Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S.; Liu, X.: Recent advances in C-S bond formation via C-H bond functionalization and decarboxylation. Chem. Soc. Rev. 44 (2015) 291–314.10.1039/C4CS00239CSearch in Google Scholar PubMed

8. Xu, J.; Shen, C.; Zhu, X.; Zhang, P.; Ajitha, M. J.; Huang, K. W.; An, Z.; Liu, X.: Remote C-H activation of quinolines through copper-catalyzed radical cross-coupling. Chem. Asian J. 11 (2016) 882–892.10.1002/asia.201501407Search in Google Scholar PubMed

9. Bruker SADABS, SMART and SAINT, Bruker AXS Inc., Madison, WI, USA, 2002.Search in Google Scholar

10. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

11. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. App. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Search in Google Scholar

Received: 2016-4-19
Accepted: 2016-8-2
Published Online: 2016-8-18
Published in Print: 2016-12-1

©2016 Wen-Bo Yu et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  49. Crystal structure of poly-[triaqua-(μ3-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′,O′′′) (2,3,4,5-tetrafluoro-benzoato-κ2O,O′) praseodymium(III)], C15H7F8O9Pr
  50. The crystal structure of dichlorido (1,3-dimesityl-1H-3λ4-imidazol-2-yl)(isoquinoline-κN)palladium(IV) – ethylacetate (1/1), C34H39Cl2N3O2Pd
  51. Crystal structure of dichlorido(1,3-bis(2,6-dimethyl-phenyl)-1H-3λ4-imidazol-2-yl)(isoquinolinyl)palladium(IV), C28H27Cl2N3Pd
  52. Crystal structure of 5-(4-(1H-tetrazol-5-yl)phenyl)-1H-imidazol-3-ium 7-carboxy-1,3-dioxo-1H,3H-benzo[de]isochromene-6-carboxylate monohydrate 4,5-anhydride, C24H16N6O8
  53. Crystal structure of poly-[diaqua-bis(μ2-2-((1H-1,2,4-triazol-5-yl)thio)acetato-κ2N:O) cadmium(II)], C8H8CdN6O6S2
  54. Crystal Structure of (E)-3-(4-methoxyphenyl)-1-(2,3,4-tris(benzyloxy)-6-hydroxyphenyl)prop-2-en-1-one, C37H32O6
  55. Structure and photochromism of 1-(1,2-dimethylindol-3-yl)-2-[2-methyl-5-(3-fluorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C26H18F7NS
  56. Crystal structure of two-dimensional coordination polymer poly-[μ2-azido-aqua-(μ2-pyrazine-2-carboxylato-κ3O,N:N′)nickel(II)], C5H5N5O3Ni
  57. Crystal structure of 2-amino-5-oxo-4-(3,5-bis(trifluoromethyl)phenyl)-4H,5H-pyrano [3,2-c]chromene-3-carbonitrile, C21H10F6N2O3
  58. Crystal structure of 4-(5-((2-methylbenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine, C21H18N4S
  59. Crystal structure of 5-(2-chloro-5-nitrophenyl)-3-(4-chlorophenyl)-N-ethyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, C18H16Cl2N4O2S
  60. Crystal structure of 4-(benzofuran-2-yl)-2-(3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl)thiazole, C28H20FN3OS
  61. Crystal structure of bis(dicyanamido-κ1N)-tetrakis[1-benzyl-1H-1,2,4-triazole-κ1N]cobalt(II), CoC40H36N18
  62. Crystal structure of 1-benzyl-6-hydroxy-1,4,5,6-tetrahydropyridine-3-carbonitrile, C13H14N2O
  63. Crystal structure of 2-amino-7-methyl-4-(3,4-difluoro-phenyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H10F2N2O3
  64. The crystal structure of 4-[(benzo[1,3]dioxol-5-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one, C19H17N3O3
  65. Crystal structure of 1,4-dihydro-1-phenylchromeno[4,3-c]pyrazole, C16H12N2O
  66. Crystal structure of N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)benzamide, C21H17N3O4S
  67. Crystal structure of 3-amino-9-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  68. Crystal structure of 1,2-bis(4-methoxyphenyl)-2-((3-(trifluoromethyl)phenyl)amino)ethan-1-one, C23H20F3NO3
  69. Crystal structure of 2-amino-4-(2,4-dinitrophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile – ethanol (1:1), C21H16N4O8
  70. Crystal structure of catena-poly-[(1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate-κ2O,O′)-(μ2-4,4′-sulfonyldibenzoato-κ4O,O′:O′′,O′′′)zinc(II)] hemihydrate, C31H27ZnFN3O9.5S
  71. Crystal structure of 2-(2-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylic acid, C12H13BrO4
  72. Crystal structure of 2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylic acid, C13H15BrO4
  73. Crystal structure of 4-(4-((3-bromophenyl)amino)-6-(tert-butyl)-3-(2-hydroxypropan-2-yl)cinnolin-8-yl)-2-methylbut-3-yn-2-ol, C26H30BrN3O2
  74. Crystal structure poly-(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazolyl-κ2NN1:N2N)-(μ3-2,2′-(1,2-phenylene)diacetato-κ5-O1,O2:O2:O3,O4)cadmium(II), C22H19CdN5O4
  75. Crystal structure of bis(1-ethyl-6-fluoro-4-oxido-7-(piperazin-1-ium-1-yl)-1,8-naphthyridin-1-ium-3-carboxylate-κ2O,O′)copper(II) benzene-1, 4-dicarboxylate dihydrate, C38H42F2CuN8O12
  76. Redetermination of the crystal structure of potassium lithium molybdate monohydrate, KLiMoO4·H2O
  77. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ3N](isonicotinate-κO) cobalt(II) [tris(2-benzimidazolylmethyl)amine-κ3N](isonicotinic acid-κO) cobalt(II) triperchlorate, C60H51N16O16Cl3Co2
  78. The crystal structure of tris(μ2-1,3-bis(4,4,4-trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-κ2O,O′)dicerium(III), C50H38F18O16Ce2
  79. Crystal structure of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-ol, C10H19NO
  80. Crystal structure of 2,4-dibenzoyl-N,N-dimethylbenzenamine, C22H19NO2
  81. The crystal structure of 2-(4-methoxyphenyl)-6,8-diphenyl-4-(phenylamino)quinazoline — acetonitrile (1/1), C35H28N4O
https://doi.org/10.1515/ncrs-2016-0127
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of the catena-poly-[bis(μ2-1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl-κN)-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)nickel(II)] 5.5 hydrate, C32H44N6NiO11F2
  3. Crystal structure of catena-poly-[(μ2-2-(2-((2,6-dimethylphenyl)amino)phenyl)acetato-κ2O:O′)(μ2-2-(2-((2,6-dimethylphenyl)amino)phenyl)acetate-κ3O,O′:O′)cadmium(II)], C28H20N2Cl4O4Cd
  4. Crystal structure of catena-poly[dichlorido-(μ2-4-(pyridin-4-yl)-isophthalate-κ2O, O′)cadmium(II)] monohydrate, C13H11NO5Cl2Cd
  5. Crystal structure of poly-{[μ2-(E)-1,4-di(1H-imidazol-1-yl)but-2-ene-κ2N:N′][μ2-cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′,O′′′]nickel(II)}, C18H22N4NiO4
  6. Crystal structure of aqua (5,5′-dicarboxy-(1,1′-biphenyl)-2,3′-dicarboxylato-κO) bis(1,10-phenanthroline-κ2N,N′)cadmium monohydrate, C40H28CdN4O10
  7. Crystal structure of 5-methoxy-N′-[(3Z)-5-chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C25H18ClFN4O3 · C2H6OS
  8. Crystal structure of 5-methoxy-N′-[(3Z)-1-benzyl-5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C27H25FN4O4S
  9. Crystal structure of poly-[bis{μ2-N-(4-(1H-imidazol-1-yl)phenyl)-4-(1H-imidazol-1-yl)-N-phenylaniline-κ2N:N′)}-(μ2-naphthalene-2,6-dicarboxylato)-(μ4-naphthalene-2,6-dicarboxylato)dicadmium(II)], C36H25N5O4Cd
  10. Crystal structure of 1-(adamantan-1-yl)-3-(4-bromophenyl)thiourea, C17H21BrN2S
  11. Crystal structure of N′-[(1E)-(2,6-dichlorophenyl)-methylidene]adamantane-1-carbohydrazide, C18H20Cl2N2O
  12. Crystal structure of dichlorido{bis(2-hydroxyethyl)-5′-([2,2′:6′,2′′-terpyridin]-4′-yl)-[1,1′:3′,1′′-terphenyl]-4,4′′-dicarboxylate-κ3N,N′,N′′}zinc(II), C39H31Cl2N3O6Zn
  13. Crystal structure of 4,4′-(1,3,5,7-tetraoxo-3a,4,4a,5,7,7a,8,8a-octahydro-4,8-ethenopyrrolo [3,4-f]isoindole-2,6(1H,3H)-diyl)dibenzoic acid, C26H18N2O8
  14. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-ethyl oxime, C17H16Cl2N2O2
  15. The crystal structure of diaqua-(N-(2-hydroxy-5-nitrobenzyl)iminodiacetato-κ4-N,O,O′,O′′)chromium(III) based on synchrotron data, C11H13CrN2O9
  16. Crystal structure of ethyl 5-amino-3-(methylthio)-1-(1-phenyl-5-(thiophen-2-yl)-1H-pyrazole-3-carbonyl)-1H-pyrazole-4-carboxylate, C21H19N5O3S2
  17. Crystal structure of (E)-1-(4-(((E)-3,5-dibromo-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C17H16Br2N2O2
  18. Crystal structure of dibromido μ-oxalato-κ2O,O′:κ2O′′,O′′′−η6-p-cymenediosmium(II), C22H28Br2O4Os2
  19. Crystal structure of 2-(bromomethyl)-4-(4-chlorophenyl)-1-tosylpyrrolidine, C18H19BrClNO2S2
  20. Crystal structure of 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; C13H11FN2O3
  21. Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C10H19N3O3
  22. Crystal structure of 1,1-dimethyl-3-(2-phenylethyl)urea, C11H16N2O
  23. Crystal structure of 2-(4-methoxyphenyl)-1,3-thiazolo[4,5-b]pyridine, C13H10N2OS
  24. Crystal structure of 3-tert-butyl-7-azadioxindole, C11H14N2O2
  25. Crystal structure of 1-ferrocenyl-6-bromopyrene, C26H17BrFe
  26. Crystal structure of 3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide, C16H13BrFN3S
  27. Crystal structure of 2-amino-4-(3,5-ditrifluoromethylphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C20H16F6N2O2
  28. The crystal structure of 2-amino-4-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13N3O4
  29. Crystal structure of 2-amino-4-(2, 4-dichlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12Cl2N2O2
  30. Crystal structure of bis(μ2-chlorido)-bis(di-p-tolylhydroxyphosphine-κP)-bis(di-p-tolylphosphite-κP)dipalladium(II), C56H58Cl2O4P4Pd2
  31. Crystal structure of diaqua-bis(2-methyl-1H-imidazole-4,5-dicarboxylato-κ2-O,N)cadmium(II) tetrahydrate, C12H22CdN4O14
  32. Crystal structure of aqua-(5-nitrosalicylato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)copper(II), C19H13CuN3O6
  33. Crystal structure of bis(4-(2-phenylpropan-2-yl)phenyl)amine, C30H31N
  34. Crystal structure of 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H16F2N2O2
  35. Crystal structure of 2-amino-4-(3,4,5-trifluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H11F3N2O2
  36. Crystal structure of an isomeric bis[(η5:η1-6,6-di-p-tolylpentafulvene)(η5-pentamethylcyclopentadienyl)titanium(III)]-μ2,η1:η1-dinitrogen complex, C60H66N2Ti2
  37. Crystal structure of 3,4-dinitropyrazole, C3H2N4O4
  38. Crystal structure of (4-vinylpyridine-κN)triphenyl tin(IV) chloride, C25H22ClNSn
  39. Crystal structure of tert-butyl 2-phenylethylcarbamate, C13H19NO2
  40. Crystal structure of (Z)-4-((E)-(4-chlorobenzyli-dene)hydrazono)-1-p-tolylpyrrolidine-3-carbonitrile, C19H17ClN4
  41. Crystal structure of bis(biphenyl-2,2′-dicarboxylato-κ2O:O′)-bis(1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)dizinc(II)2.5 hydrate, C62H57N6Zn2O16.5F2
  42. Crystal structure of dichloridobis{μ2-2,2′-((1E,1′E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(4-chlorophenolato)-κ5O,N,N′,O′:O′}diiron(III), C32H24Cl6Fe2N4O4
  43. Crystal structure of 4-((4,4-dimethyl-2, 6-dioxocyclohexylidine)methylamino)-N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide, C20H23N3O5S
  44. Crystal structure of poly-[aqua-μ2-aqua-μ2-(4,4′-oxybis(benzoato)-κ4O,O′:O′′,O′′′)cadmium(II)], C14H12O7Cd
  45. Crystal structure of aqua(μ2-biphenyl-2,2′-dicarboxylato-κ3O,O′:O′′)-(μ2-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)cadmium(II) 1.5 hydrate, C62H60N6Cd2O19F2
  46. Crystal structure of dimethanolo-bis[μ-(2-(2-(5-(pyridin-2-yl)-1H-1,2,4-triazol-3-yl)phenoxy)benzoato)-κ5O,O′,N:N′,N′′]dicopper(II) — methanol (1/2), C46H48Cu2N8O12
  47. Crystal structure of poly-[tetraaqua-bis(μ4-2,5-dibenzoyl-1,4-benzenedicarboxylato-κ4O1:O2:O3:O4)-μ2-2,5-dibenzoyl-1,4-benzenedicarboxylato-k4O5,O6: O5′,O6′-didysprosium(III)] tetrahydrate C33H26O13Dy
  48. Crystal structure of hexaaqua-bis(3-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl) propionato-κ3O,O′:O′)-bis(3-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)propionato-κO)-bis(3-(3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)propionato-κ2O,O′)dineodymium(III) octahydrate, C60H76N18O32Nd2
  49. Crystal structure of poly-[triaqua-(μ3-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′,O′′′) (2,3,4,5-tetrafluoro-benzoato-κ2O,O′) praseodymium(III)], C15H7F8O9Pr
  50. The crystal structure of dichlorido (1,3-dimesityl-1H-3λ4-imidazol-2-yl)(isoquinoline-κN)palladium(IV) – ethylacetate (1/1), C34H39Cl2N3O2Pd
  51. Crystal structure of dichlorido(1,3-bis(2,6-dimethyl-phenyl)-1H-3λ4-imidazol-2-yl)(isoquinolinyl)palladium(IV), C28H27Cl2N3Pd
  52. Crystal structure of 5-(4-(1H-tetrazol-5-yl)phenyl)-1H-imidazol-3-ium 7-carboxy-1,3-dioxo-1H,3H-benzo[de]isochromene-6-carboxylate monohydrate 4,5-anhydride, C24H16N6O8
  53. Crystal structure of poly-[diaqua-bis(μ2-2-((1H-1,2,4-triazol-5-yl)thio)acetato-κ2N:O) cadmium(II)], C8H8CdN6O6S2
  54. Crystal Structure of (E)-3-(4-methoxyphenyl)-1-(2,3,4-tris(benzyloxy)-6-hydroxyphenyl)prop-2-en-1-one, C37H32O6
  55. Structure and photochromism of 1-(1,2-dimethylindol-3-yl)-2-[2-methyl-5-(3-fluorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C26H18F7NS
  56. Crystal structure of two-dimensional coordination polymer poly-[μ2-azido-aqua-(μ2-pyrazine-2-carboxylato-κ3O,N:N′)nickel(II)], C5H5N5O3Ni
  57. Crystal structure of 2-amino-5-oxo-4-(3,5-bis(trifluoromethyl)phenyl)-4H,5H-pyrano [3,2-c]chromene-3-carbonitrile, C21H10F6N2O3
  58. Crystal structure of 4-(5-((2-methylbenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine, C21H18N4S
  59. Crystal structure of 5-(2-chloro-5-nitrophenyl)-3-(4-chlorophenyl)-N-ethyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, C18H16Cl2N4O2S
  60. Crystal structure of 4-(benzofuran-2-yl)-2-(3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl)thiazole, C28H20FN3OS
  61. Crystal structure of bis(dicyanamido-κ1N)-tetrakis[1-benzyl-1H-1,2,4-triazole-κ1N]cobalt(II), CoC40H36N18
  62. Crystal structure of 1-benzyl-6-hydroxy-1,4,5,6-tetrahydropyridine-3-carbonitrile, C13H14N2O
  63. Crystal structure of 2-amino-7-methyl-4-(3,4-difluoro-phenyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H10F2N2O3
  64. The crystal structure of 4-[(benzo[1,3]dioxol-5-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one, C19H17N3O3
  65. Crystal structure of 1,4-dihydro-1-phenylchromeno[4,3-c]pyrazole, C16H12N2O
  66. Crystal structure of N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)benzamide, C21H17N3O4S
  67. Crystal structure of 3-amino-9-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  68. Crystal structure of 1,2-bis(4-methoxyphenyl)-2-((3-(trifluoromethyl)phenyl)amino)ethan-1-one, C23H20F3NO3
  69. Crystal structure of 2-amino-4-(2,4-dinitrophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile – ethanol (1:1), C21H16N4O8
  70. Crystal structure of catena-poly-[(1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate-κ2O,O′)-(μ2-4,4′-sulfonyldibenzoato-κ4O,O′:O′′,O′′′)zinc(II)] hemihydrate, C31H27ZnFN3O9.5S
  71. Crystal structure of 2-(2-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylic acid, C12H13BrO4
  72. Crystal structure of 2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylic acid, C13H15BrO4
  73. Crystal structure of 4-(4-((3-bromophenyl)amino)-6-(tert-butyl)-3-(2-hydroxypropan-2-yl)cinnolin-8-yl)-2-methylbut-3-yn-2-ol, C26H30BrN3O2
  74. Crystal structure poly-(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazolyl-κ2NN1:N2N)-(μ3-2,2′-(1,2-phenylene)diacetato-κ5-O1,O2:O2:O3,O4)cadmium(II), C22H19CdN5O4
  75. Crystal structure of bis(1-ethyl-6-fluoro-4-oxido-7-(piperazin-1-ium-1-yl)-1,8-naphthyridin-1-ium-3-carboxylate-κ2O,O′)copper(II) benzene-1, 4-dicarboxylate dihydrate, C38H42F2CuN8O12
  76. Redetermination of the crystal structure of potassium lithium molybdate monohydrate, KLiMoO4·H2O
  77. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ3N](isonicotinate-κO) cobalt(II) [tris(2-benzimidazolylmethyl)amine-κ3N](isonicotinic acid-κO) cobalt(II) triperchlorate, C60H51N16O16Cl3Co2
  78. The crystal structure of tris(μ2-1,3-bis(4,4,4-trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-κ2O,O′)dicerium(III), C50H38F18O16Ce2
  79. Crystal structure of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-ol, C10H19NO
  80. Crystal structure of 2,4-dibenzoyl-N,N-dimethylbenzenamine, C22H19NO2
  81. The crystal structure of 2-(4-methoxyphenyl)-6,8-diphenyl-4-(phenylamino)quinazoline — acetonitrile (1/1), C35H28N4O
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