Home The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
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The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S

  • Lianqing Chen EMAIL logo and Lijun Tian
Published/Copyright: June 24, 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

C12H6N4Cl2F6O3S, orthorhombic, Pna21 (no. 33), a = 18.7340(10) Å, b = 9.4010(10) Å, c = 19.2330(10) Å, V = 3387.3(4) Å3, Z = 8, Rgt(F) = 0.0449, wRref(F2) = 0.1074, T = 100.15 K.

CCDC no.: 1920632

The crystal 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.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.15 × 0.12 × 0.1 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.59 mm−1
Diffractometer, scan mode:Bruker D8 Venture, φ and ω-scans
θmax, completeness:27.7°, >99%
N(hkl)measured, N(hkl)unique, Rint:19660, 6747, 0.056
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5379
N(param)refined:534
Programs:CrysAlisPRO [1], SHELX [2], [3], DIAMOND [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.77185(7)0.90346(17)0.43825(8)0.0287(3)
Cl20.61800(8)0.59394(17)0.61913(8)0.0293(3)
Cl30.47759(8)0.40557(17)0.55889(8)0.0288(3)
Cl40.63223(8)0.08968(17)0.38111(8)0.0319(4)
S10.51646(7)0.62475(15)0.34512(7)0.0192(3)
S20.73035(7)0.13112(15)0.65853(7)0.0192(3)
F10.4945(2)0.8637(4)0.2803(2)0.0373(9)
F20.5986(3)0.7760(5)0.2649(3)0.0478(13)
F30.5083(2)0.6836(5)0.21449(19)0.0464(11)
F40.8556(3)0.8044(7)0.7357(3)0.0693(16)
F50.8949(3)0.6210(5)0.6908(3)0.0675(17)
F60.9302(3)0.8211(7)0.6519(3)0.0680(16)
F70.7493(2)0.3761(4)0.7188(2)0.0436(10)
F80.6460(3)0.2873(6)0.7328(3)0.0507(13)
F90.7348(3)0.2006(6)0.7881(2)0.0575(13)
F10a0.3505(8)0.0920(15)0.3202(8)0.044(3)
F10Ab0.3338(6)0.1228(13)0.3388(6)0.052(3)
F11a0.3831(7)0.290(2)0.2730(8)0.061(4)
F11Ab0.3951(5)0.2088(12)0.2597(4)0.050(2)
F12a0.3129(6)0.2889(15)0.3575(7)0.046(3)
F12Ab0.3376(6)0.3503(11)0.3229(6)0.066(3)
O10.5552(2)0.5006(4)0.3269(2)0.0280(10)
O20.4409(2)0.6187(4)0.3534(2)0.0259(9)
O30.46079(19)0.9778(4)0.5207(2)0.0218(9)
O40.80578(19)0.1257(4)0.6527(2)0.0258(9)
O50.6913(2)0.0076(5)0.6775(2)0.0305(11)
O60.78642(19)0.4813(4)0.4827(2)0.0225(9)
N10.6395(4)0.7557(5)0.4884(4)0.0189(16)
N20.5808(2)0.8340(5)0.5089(3)0.0202(10)
N30.6761(2)0.5941(5)0.4029(2)0.0191(10)
H3A0.7195320.5911080.4203790.023*
H3B0.6655010.5431010.3659730.023*
N40.4077(2)0.8576(5)0.4358(3)0.0221(10)
H4A0.3674540.9041950.4418110.026*
H4B0.4107780.7916990.4033920.026*
N50.6096(3)0.2523(5)0.5100(4)0.0163(15)
N60.6676(2)0.3314(5)0.4908(2)0.0182(10)
N70.5716(2)0.0957(5)0.5987(2)0.0192(10)
H7A0.5290280.0883690.5797780.023*
H7B0.5815690.0489230.6371310.023*
N80.8405(2)0.3569(5)0.5657(3)0.0243(11)
H8A0.8805590.4045170.5600110.029*
H8B0.8379530.2891010.5970990.029*
C10.7624(3)0.8194(6)0.5164(3)0.0199(12)
C20.6985(4)0.7525(6)0.5345(5)0.0175(19)
C30.5315(3)0.8069(6)0.4633(3)0.0164(11)
C40.5560(3)0.7070(7)0.4126(3)0.0162(11)
C50.5312(5)0.7447(7)0.2705(5)0.031(2)
C60.6271(3)0.6750(6)0.4320(3)0.0154(11)
C70.4631(3)0.8863(6)0.4749(3)0.0177(11)
C80.6945(3)0.6836(6)0.5977(3)0.0189(12)
C90.7504(3)0.6837(6)0.6440(3)0.0227(12)
H90.7463150.6378940.6878480.027*
C100.8122(4)0.7518(6)0.6252(5)0.0232(19)
C110.8737(5)0.7501(7)0.6748(5)0.033(2)
C120.8200(3)0.8194(6)0.5614(3)0.0210(12)
H120.8636640.8643150.5490380.025*
C130.4862(3)0.3155(6)0.4818(3)0.0184(12)
C140.5495(4)0.2477(5)0.4657(5)0.0171(19)
C150.7168(3)0.3062(6)0.5373(3)0.0156(11)
C160.6917(3)0.2080(7)0.5881(3)0.0161(11)
C170.7145(5)0.2557(7)0.7275(5)0.031(2)
C180.6212(3)0.1776(6)0.5691(3)0.0147(11)
C190.7848(3)0.3870(6)0.5273(3)0.0177(11)
C200.5551(3)0.1765(6)0.4025(3)0.0216(13)
C210.4983(3)0.1723(6)0.3573(3)0.0250(13)
H210.5023980.1246550.3139700.030*
C220.4343(4)0.2392(7)0.3760(5)0.026(2)
C230.3729(5)0.2293(10)0.3264(6)0.041(2)
C240.4289(3)0.3098(6)0.4371(3)0.0245(13)
H240.3853640.3554700.4492310.029*

  1. Occupancy: a = 0.406(15), b = 406(15)

Source of materials

All chemical solvents and reagents were of analytical grade quality, which were obtained from commercial suppliers and used directly without further purification (Shanghai Guoyao Chemical Reagent Co., Ltd.). Doubly distilled water was used throughout all experiments.

To a 100 mL flask, 9.10 g (96%, 0.02 mol) of fipronil and 30 mL of DMSO were added, and 2.76 g of potassium carbonate was added to the reaction mixture and stirred well. 15 mL of H2O2 (30%) was slowly added to the flask under ice-water bath, and a dry tube containing calcium chloride was attached to the top of the flask. Stirred until no significant bubbles were formed and reacted overnight at room temperature. After the reaction was completed, the reaction solution was cooled, and transferred to a 250 mL separatory funnel. After extracting with 100 mL of distilled water and 30 mL of ethyl acetate, the organic phase was dried over MgSO4 and filtered, and the filtrate was evaporated by rotary evaporation, and then adsorbed on activated silica gel (10 g). The crude product was obtained by column chromatography, which was washed several times with petroleum ether, filtered and dried under vacuum. The compound 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide was obtained. Yield: 8.22 g (87.5%), 1H NMR (CDCl3, 400MHz, ppm) 8.28 (s, 2H, Ar–H), 7.80 (s, 1H, N–H), 7.60 (s, 1H, N–H), 7.40 (s, 2H, C–NH2). IR (KBr, I/cm-1) : 3390, 3293 (N–H), 3120 (benzene C–H), 1681 (C=O), 1645 (C=N), 1567, 1467, 1354 (benzene skeleton), 1312 (C–F), 882, 819 (aromatic ring C–H). Calcd for C12H6N4Cl2F6O3S: C, 30.59; H, 1.28; N, 11.89%, found C, 30.51; H, 1.24; N, 11.86%. MS (FAB): m/e, 469.94 (M+).

After allowing the Vethyl acetate/Vpetroleum ether (1:4) to stand in air for 10 days, colorless block crystals were formed by slow evaporation of the solvent. The single crystals were isolated, washed with light petroleum and dried under vacuum (yield 88.2%).

Experimental details

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq for aryl H atoms and 1.5 Ueq for the methyl H atoms. Methyl H atoms were allowed to rotate to best fit the experimental electron density. The CF3 group was refined with a disorder model. Atom F10, F11 and F12 of the CF3 moiety were found to be disordered over three positions (F10/F10A, F11/F11A and F12/F12A) and split into two positions with occupancies of 0.53323 and 0.46677 and refined anisotropically.

Comment

As a typical representative of phenylpyrazole pesticides, fipronil is the first commercial phenylpyrazole insecticide for pest control [5], which is highly effective against soil insects, such as wireworms and aquatic insects, with extended use in the control of many agricultural vermin on various crops, such as water rice weevil and locust [6]. The molecular structure of fipronil contains a trifluoromethylsulfinyl substituent that is not present in any other agrochemicals, which is thought to contribute to its remarkable potency in the insecticidal field [7]. However, Fipronil is not easy to be degraded under the natural light irritation [8]. Sulfone compounds are a class of compounds with high biological activity and have a broad spectrum of biological activities [9], [10]. They are widely used as fungicides, herbicides and antitumor drugs in the fields of medicine and pesticides [11]. To ensure the safe use of fipronil, prevent ecological pollution and ensure the safety of humans and animals, we have employed a facile one-pot method to prepare fipronil sulfone hydrolysate by using fipronil as a lead compound.

The structure of title compound consisted of a benzene moiety and a pyrazole ring. The benzene ring and pyrazole ring in the same phenylpyrazole moiety (molecule 1; see the figure) made a dihedral angle of 51.34(3)°, which was similar to the molecular structure of Fipronil [12]. In each phenylpyrazole moiety, 1,3-dichloro-5-(trifluoro-methyl)phenyl ring was almost perpendicular to the plane of pyrazole ring. Each free trifluoromethyl group was twisted out of the pyrazole plane by rotation of the C-S single bond. The C(3)-N(2) and C(6)-N(1) (pyrazole) bond distance were 1.299(7) Å and 1.343(8) Å, respectively, which were smaller than the value of 1.417(10) Å observed in the C(2)-N(1) bond. The bond of C(11)-F(4), C(11)-F(5) and C(11)-F(6) (CF3 group connecting with phenyl unit) were 1.321(10) Å, 1.314(8) Å and 1.326(9) Å, respectively, which were longer than the average value of 1.308(10) Å observed in the trifluoromethyl sulfonyl group. The C(4)-S(1) (sulfonyl) bond distance was 1.683(6) Å, which was smaller than the value of 1.845(9) Å observed in the C(5)-S(1) bond. The S(1)-O(2) (sulfonyl) bond distance was 1.425(4) Å, which was longer than the value of 1.419(4) Å observed in the S(1)-O(1) bond.

The packing of the title compound was partially facilitated by intramolecular and intermolecular H-bonds [13]. The intramolecular H-bonds of the title compound were O(2)—H(4b), O(4)—H(8b) and O(6)—H(3a), respectively. These H-bond lengths were 2.8173(3)°, 2.8149(3)° and 2.7831(3)°, respectively [14].

The bioactivities of the title compound and phenylpyrazole insecticide (fipronil) against the 3rd instar larvae of Plutella xylostella were tested by the leaf disc-dipping assay. The compound was dissolved in acetone and suspended in distilled water containing Triton X-100. Distilled water containing acetone-Triton X-100 solution was used as the control. Leaves of Chinese cabbage grown in the greenhouse were collected and discs (5 cm in diameter) were punched from each leaf. The leaf discs were dipped into each test solution for 40 seconds and allowed to dry for 2.0 hours. The treated leaf discs were placed in a Petri dish (10 cm in diameter). Then, fifteen Plutella xylostella larvae were introduced into each dish. Petri dishes were kept in incubator at 27 °C and 86% relative humidity under a photoperiod of 15:9 h light: dark. All treatments were replicated five times. Mortalities were determined 24 h after treatment. The death rate of each treatment group was confirmed. LC50 value was calculated by the SPSS. The insecticidal bioactivities result displayed that the activities of title compounds against Plutella xylostella after 24 h was 16.23 mg⋅L−1 better than that of fipronil 26.41 mg⋅L−1.

Funding source: Natural Science Foundation of Hubei province for Distinguished Young Scholars

Award Identifier / Grant number: 2013CFA034

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 20702064

Award Identifier / Grant number: 21177161

Award Identifier / Grant number: 31402137

Funding source: Program for Excellent Talents in Hubei Province

Award Identifier / Grant number: RCJH15001

Funding source: Opening Project of Key Laboratory of Green Catalysis of Sichuan Institutes of High Education

Award Identifier / Grant number: LYZ1107

Funding source: Central University, South-Central University for Nationalities

Award Identifier / Grant number: CZP17077

Funding statement: The authors thank the Natural Science Foundation of Hubei province for Distinguished Young Scholars (No. 2013CFA034); National Natural Science Foundation of China (grant No. 20702064, 21177161 and 31402137); the Program for Excellent Talents in Hubei Province (RCJH15001); the Opening Project of Key Laboratory of Green Catalysis of Sichuan Institutes of High Education (LYZ1107) and the Fundamental Research Funds for the Central University, South-Central University for Nationalities (CZP17077).

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Received: 2019-04-30
Accepted: 2019-06-04
Published Online: 2019-06-24
Published in Print: 2019-11-26

©2019 Lianqing Chen 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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  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
https://doi.org/10.1515/ncrs-2019-0310
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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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