Home Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
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Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S

  • Lianqing Chen EMAIL logo and Zhongda Wu
Published/Copyright: March 11, 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

C20H12N4Cl2F6O2S, triclinic, P1̄ (no. 2), a = 8.581(3) Å, b = 10.967(4) Å, c = 13.802(5) Å, α = 106.287(4)°, β = 105.505(4)°, γ = 101.592(4)°, V = 1146.7(7) Å3, Z = 2, Rgt(F) = 0.0500, wRref(F2) = 0.1426, T = 173 K.

CCDC no.: 1896149

The asymmetric unit of the title crystal 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:Colourless block
Size:0.20 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.45 mm−1
Diffractometer, scan mode:CCD, φ and ω
θmax, completeness:27.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:8996, 4840, 0.047
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3883
N(param)refined:348
Programs:CrysAlisPRO [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.42976(7)0.64428(6)0.46938(5)0.02837(17)
Cl20.12755(8)0.22127(6)0.10049(5)0.03224(18)
S10.58199(7)0.67201(6)0.09013(5)0.02390(17)
F10.6659(2)0.88764(15)0.26399(13)0.0397(4)
F20.86959(19)0.80324(16)0.25479(15)0.0467(5)
F30.7904(2)0.90945(17)0.15035(16)0.0573(5)
O10.6947(2)0.60694(18)0.04333(14)0.0314(4)
O20.3537(2)1.07381(17)0.40044(15)0.0345(4)
N10.3930(2)0.47616(18)0.25036(16)0.0212(4)
N20.5489(2)0.4542(2)0.27234(17)0.0253(5)
N30.2240(2)0.57975(19)0.15852(17)0.0219(4)
H30.146(4)0.549(3)0.177(2)0.026*
N40.9221(3)0.5047(3)0.2248(2)0.0387(6)
C10.2862(3)0.4873(2)0.3982(2)0.0228(5)
C20.2757(3)0.4200(2)0.29383(19)0.0212(5)
C30.6278(3)0.5235(2)0.2263(2)0.0231(5)
C40.5278(3)0.5920(2)0.17467(19)0.0220(5)
C50.7361(3)0.8270(2)0.1972(2)0.0317(6)
C60.3725(3)0.5558(2)0.18978(18)0.0200(5)
C70.1827(3)0.6551(2)0.0879(2)0.0250(5)
H7A0.05810.63620.05970.030*
H7B0.22020.62400.02590.030*
C80.2637(3)0.8046(2)0.1430(2)0.0236(5)
C90.2717(3)0.8661(2)0.2480(2)0.0252(5)
H90.23020.81430.28570.030*
C100.3409(3)1.0042(2)0.2981(2)0.0278(5)
C110.2849(4)1.0000(3)0.4585(2)0.0374(6)
H11A0.16310.95740.42010.056*
H11B0.30361.06050.53070.056*
H11C0.34130.93160.46420.056*
C120.4030(3)1.0798(2)0.2425(2)0.0327(6)
H120.45161.17350.27640.039*
C130.3935(4)1.0181(3)0.1386(2)0.0348(6)
H130.43511.06990.10100.042*
C140.3236(3)0.8806(3)0.0878(2)0.0297(6)
H140.31690.83910.01580.036*
C150.7929(3)0.5144(3)0.2259(2)0.0285(5)
C160.1529(3)0.2977(2)0.2339(2)0.0241(5)
C170.0494(3)0.2382(2)0.2801(2)0.0274(5)
H17−0.03240.15360.24000.033*
C180.0677(3)0.3046(2)0.3860(2)0.0266(5)
C19−0.0419(4)0.2381(3)0.4364(3)0.0392(7)
C200.1832(3)0.4296(2)0.4452(2)0.0251(5)
H200.19150.47490.51690.030*
F4a−0.0202(4)0.3086(3)0.5348(2)0.0628(11)
F5a−0.0321(5)0.1164(3)0.4271(3)0.0682(10)
F6a−0.2091(3)0.2166(3)0.3821(3)0.0687(10)
F4Ab−0.135(2)0.2866(16)0.4619(16)0.073(4)
F5Ab−0.1058(18)0.1210(16)0.3930(11)0.058(4)
F6Ab0.0812(14)0.2373(13)0.5368(9)0.060(4)

  1. aOccupancy: 0.826(5), bOccupancy: 0.174(5).

Source of material

All chemicals were of analytical grade, 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. The synthesis of the target product involves two steps. Firstly, to a 10 mL toluene solution of fipronil (4.37 g, 10 mmol), we added a 12 mmol m-methoxybenzaldehyde in toluene (35 mL) and 4 Å molecular sieves (2.0 g). Furthermore p-toluene sulfonic acid (0.2 g) was added as a catalyst followed by ultrasonic stirring for 0.5 h, the reaction mixture was reacted at about 120 °C for 8 h. The resulting solution was cooled to room temperature, and the filtrate was washed with saturated sodium carbonate solution (30 mL), water and saturated brine, respectively, and then dried over MgSO4. The filtrate was concentrated by rotary evaporation, and adsorbed on activated silica gel. The crude product was obtained by column chromatography on silica gel with Vethyl acetate/Vpetroleum ether (1:8) as the eluent, which was dried under vacuum to give the compound (1) 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-[(3-methoxy-benzylidene)-amino]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile. Yield: 2.90 g (66.4%), 1H NMR (CDCl3, 400 MHz, ppm) δ 3.79(s, 3H), 7.14(s, 1H), 7.27 (s, 1H), 7.37 (s, 2H), 7.75 (s, 1H), 7.83 (s, 1H), 8.85 (s, 1H). IR (KBr, ν, cm−1) : 3075 (Ar-H), 2251 (–C≡N), 1599 (—C≡N), 1575, 1545, 1507 (benzene ring skeleton vibration), 1315 (C—F), 789, 685 (C—H). MS (FAB): m/e, 553 (M+).

In the second step, to a solution of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-[(3-methoxy-benzylidene)-amino]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile (1.65 g, 3 mmol), NaBH4 in CH2Cl2 (25 mL) was added an stirred for 4 h. The filtrate was concentrated by rotary evaporation, and adsorbed on activated silica gel (2.0 g), the crude product was obtained by column chromatography on silica gel with ethyl acetate, which was dried under vacuum to give the title compound. Yield: 1.22 g (74.1%), 1H NMR (CDCl3, 400 MHz, ppm) δ 3.75 (s, 3H), 4.11 (d, J = 8.4 Hz, 2H), 6.44 (s, 1H), 6.51 (s, 2H), 6.76 (d, J = 8.7 Hz, 1H), 7.12 (s, 1H), 7.55 (s, 1H), 7.61 (s, 1H). IR(KBr, ν, cm−1) : 3321 (Ar—H), 3045 (Ar—H), 2256 (—C≡N), 1586, 1545, 1496 (benzene ring skeleton vibration), 1316 (C—F), 769, 655 (aromatic ring C—H). MS (FAB): m/e, 556 (M+).

After allowing the Vethyl acetate/Vpetroleum ether (1:4) solution to stand in air for 15 days, transparent colorless cubic crystals were formed by slow evaporation of the solvent. The crystals of the title compound were isolated, washed with light petroleum and dried in vacuum (yield 70.4%).

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. All H atoms in the methyl group were allowed to rotate to best fit the experimental electron density. The CF3 group was refined with a disorder model. Atom F4, F5 and F6 of the CF3 moiety were found to be disordered over three positions (F4/F4A, F5/F5A and F6/F6A) and split into two positions with occupancies of 0.604 and 0.396 and refined anisotropically.

Comment

Schiff base reduction derivatives are important chemical reagents, which act as a foundational role of antibacterial, anti-oxidation, anti-tumor and have a wide range of applications in the fields of catalysis, biochemistry, functional materials, medicine and other research areas [5]. Some Schiff base reduction derivatives have a strong coordination effect [6]. Recently, such compounds are identified as potential components in the luminescent materials. Phenylpyrazole derivatives are a class of nitrogen-containing heterocyclic compounds with broad biological activity [7]. In the field of medicine, such compounds can reduce inflammation and analgesia [8] and in the field of pesticides, they can be used as herbicides and pesticides [9]. Furthermore, from the perspective of the molecular structure, the phenylpyrazole heterocycle can form a conjugated system with high fluorescence quantum yield and intramolecular charge transfer characteristics.

The crystal structure of the title compound consists of a fipronil sub structure and a m-methoxybenzaldehyde moiety, and is bridged with C—N bond 1.464(3) Å formed by N3—C7. The bridge angle C7—N3—C6 is 124.9(2)°. In the crystal structure the 1,3-dichloro-5-(trifluoromethyl)benzene rings are not coplanar to the plane of the pyrazole ring [10]. The two heterocyclic rings make a dihedral angle of C6—N1—C2 127.65(18)°. The N1—C2 bond distance is 1.425(3) Å, which is the single bond connecting pyrazole ring to 2,6-dichloro-4-trifluoromethylphenyl. The mean plane of C4-S1-C5 is slightly twisted out of pyrazole ring with a dihedral angle of 97.29(12)°. The aryl moieties of 1,3-dichloro-5-(trifluoromethyl)benzene, pyrazole and m-methoxybenzene are not in the same plane [11]. The C4—S1, S1—O1 and C10—O2 bond distance are 1.746(2) Å, 1.4879(18) Å and 1.368(3) Å respectively. The N4—C15 bond distance is 1.139(3) Å.

The packing of the title compound is partially facilitated by Y—X⋯π interactions. The two most prominent such interactions are given in the Y-X⋯Cg (Pi-Ring) interactions table (Cg1 represents the centroid of ring N1/N2/C4/C2/C3, Cg2 that of C7/C12/C11/C10/C9/C8). The first of these interactions, C8—Cl(2)⋯C(g)1π which acts in centrosymmetric pairs between two molecules, connects the molecules to infinite chains along the c axis of the unit cell. The second slightly weaker type of C19—F6A⋯C(g)2π interaction connects these chains with each other. There are no classical intermolecular hydrogen bonds.

The bioactivities of the title compound and phenylpyrazole insecticide (fipronil) against the 3rd instar larvae of Plutella xylostella were determined by the leaf disc-dipping assay. Leaves of Chinese cabbage grown in the greenhouse were collected, and discs (5 cm diameter) were punched from each leaf. The compounds were dissolved in acetone and suspended in distilled water containing Triton X-100. Leaf discs were dipped in each test solution for 30 s and allowed to dry for 2 h. The treated leaf discs were placed into Petri dishes (10 cm diameter). Then, ten Plutella xylostella larvae were introduced into each dish. Doubly distilled water containing acetone-Triton X-100 solution was used as the control. Petri dishes were kept in incubator at 25 °C and 85% relative humidity under a photoperiod of 16:8 h light: dark. All treatments were replicated three times. Mortalities were determined 24 h after treatment. The death rate of each treatment group was confirmed. LC50 value was calculated by the SPSS. Bioactivity results showed that the activities of the title compounds against Plutella xylostella after 24 h is 14.34 mg⋅L−1 better than that of fipronil 27.24 mg⋅L−1. This approach proposes a novel insight to provide a great number of novel phenylpyrazole fluorescent insecticide by a general green method.

The absorption and photoluminescence spectra of the title compound in CH2Cl2 solution were investigated. In the absorption spectrum, intense absorptions are observed in the ultraviolet region near 210 nm and 275 nm, belonging to the conjugated absorption peak of benzene ring and pyrazole ring. The conjugated structure with the pyrazole ring, results in a red shift in UV absorption and a medium-intensity absorption peak at 320-387 nm. Its UV absorption is mainly attributed to the p-π* transition of the conjugated system. The fluorescence spectrum of the title compound shows a strong peak at 445 nm. Finally it should be mentioned that phenylpyrazole heterocycle compounds are good candidates to design and develop new fluorescent pesticides, which lays a foundation for the natural degradation and fluorescence detection of pesticide residues.

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 20702064

Award Identifier / Grant number: 21177161

Award Identifier / Grant number: 31402137

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: 2019-01-20
Accepted: 2019-02-08
Published Online: 2019-03-11
Published in Print: 2019-06-26

© 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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  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-2019-0065
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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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