Home The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
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The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S

  • Lianqing Chen ORCID logo EMAIL logo , Long Zhang , Chenglong Tang and Zhongda Wu
Published/Copyright: March 5, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 3

Abstract

C22H15N3Cl2F6O4S, monoclinic, P1̄ (no. 14), a = 13.6099(10) Å, b = 12.0571(9) Å, c = 16.2351(13) Å, α = 90°, β = 112.714(2)°, γ = 90°, V = 1146.7(7) Å3, Z = 4, Rgt(F) = 0.0419, wRref(F2) = 0.1087, T = 173 K.

CCDC no.: 1981096

The molecular 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:Colourless block
Size:0.11 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.43 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:32747, 5048, 0.065
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3776
N(param)refined:365
Programs:CrysAlisPRO [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.64428(5)0.40984(5)0.32028(4)0.03194(16)
Cl20.95717(5)0.60071(5)0.59897(4)0.02916(16)
S10.66553(5)0.32083(5)0.67938(4)0.02626(16)
F10.73916(14)0.34879(15)0.85167(11)0.0457(4)
F20.85658(13)0.28402(16)0.80652(12)0.0503(5)
F30.81536(15)0.45606(14)0.78981(11)0.0504(5)
F40.98330(11)0.68408(15)0.27405(11)0.0405(4)
F50.81942(12)0.70765(14)0.18918(10)0.0382(4)
F60.89606(15)0.82160(13)0.29631(12)0.0483(5)
O10.58367(13)0.40576(16)0.67148(12)0.0318(4)
O20.63617(14)0.69185(16)0.76076(11)0.0329(4)
O30.87976(17)0.12062(15)0.56810(13)0.0404(5)
O40.78788(18)0.12097(16)0.65830(15)0.0469(5)
N10.78450(15)0.43550(16)0.51083(13)0.0205(4)
N20.82589(15)0.33135(16)0.52064(13)0.0223(4)
N30.67546(15)0.55701(16)0.55107(13)0.0219(4)
C10.74978(18)0.50129(18)0.36041(16)0.0207(5)
C20.80615(18)0.50982(18)0.45202(15)0.0191(5)
C30.79293(18)0.28412(19)0.57945(16)0.0224(5)
C40.73337(18)0.3582(2)0.61005(15)0.0218(5)
C50.7774(2)0.3549(2)0.78808(17)0.0303(6)
C60.72765(18)0.45682(19)0.56288(15)0.0204(5)
C70.65873(18)0.5996(2)0.61674(16)0.0227(5)
H70.6896460.5656450.6738420.027*
C80.59356(18)0.6986(2)0.60634(16)0.0219(5)
C90.58016(19)0.7441(2)0.68174(16)0.0250(5)
C100.6125(2)0.7209(2)0.83648(17)0.0335(6)
H10A0.5366610.7081440.8227560.050*
H10B0.6292550.7993360.8509460.050*
H10C0.6552700.6751050.8876490.050*
C110.51599(19)0.8354(2)0.67261(18)0.0285(6)
H110.5055720.8647010.7229620.034*
C120.4666(2)0.8843(2)0.58930(19)0.0325(6)
H120.4233080.9479630.5834020.039*
C130.4793(2)0.8421(2)0.51434(19)0.0331(6)
H130.4457410.8767180.4577620.040*
C140.54167(19)0.7487(2)0.52376(17)0.0260(5)
H140.5491810.7180080.4725940.031*
C150.8192(2)0.1672(2)0.60689(18)0.0311(6)
C16a0.9164(5)0.0072(4)0.5912(4)0.0423(13)
H16Aa0.923694−0.0094880.6529810.051*
H16Ba0.986786−0.0028060.5875210.051*
C17a0.8362(4)−0.0697(3)0.5267(3)0.0511(15)
H17Aa0.766875−0.0595120.5309120.077*
H17Ba0.859659−0.1466650.5414660.077*
H17Ca0.829945−0.0531250.4657970.077*
C180.88701(18)0.58849(19)0.48496(16)0.0204(5)
C190.91300(18)0.65671(19)0.42771(16)0.0219(5)
H190.9674520.7109980.4503990.026*
C200.85733(18)0.64378(19)0.33603(16)0.0218(5)
C210.8882(2)0.7143(2)0.27387(18)0.0284(6)
C220.77605(18)0.5667(2)0.30133(16)0.0234(5)
H220.7391370.5588290.2386430.028*
C16Ab0.874(2)−0.005(2)0.5890(18)0.040(5)
H16Cb0.914532−0.0215180.6530520.048*
H16Db0.799679−0.0305740.5713990.048*
C17Ab0.9251(18)−0.0546(15)0.5324(11)0.049(6)
H17Db0.874905−0.0538260.4699720.074*
H17Eb0.945612−0.1313090.5513050.074*
H17Fb0.988649−0.0116980.5384350.074*

  1. aOccupancy: 0.812(9), bOccupancy: 0.188(9).

Source of material

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

The synthesis of the target product is divided into two processes. In the first step, 5 mmol of fipronil was placed into a 100 mL round bottom flask, 1 mmol of anhydrous FeCl3 and 30.0 mL of ethanol were added and refluxed at 90 °C for 10 h. After the reaction was completed, the device was cooled to room temperature, and the reaction solution was transferred to a 100 mL rotary distillation bottle. The solvent was removed to obtain a brown-red thick liquid. We extacted with 30.0 mL of ethyl acetate and 80.0 mL of water, collected the organic phase, transferred the organic phase to a rotary flask, and added 3.0 g of silica gel for drying sample preparation. Finally, different proportions of ethyl acetate and petroleum ether were used as developing agents and separated by chromatography to obtain the intermediate product esterified fipronil: ethyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carboxylate. Yield: 3.60 g (82.4%), 1H NMR (CDCl3, 400 MHz, ppm), δ 1.42–1.46 (t, J = 16.0 Hz, 3H, CH2—H), 3.89 (s, J = 12.0 Hz, 3H, O—CH3), 4.47–4.49 (q, J = 7.2 Hz, 2H, CH—H), 6.91–6.93 (t, J = 7.2 Hz, 2H, Ar—H), 7.72–7.74 (m, 4H, Ar—H), 9.39 (s, 1H, CH=N). IR (KBr, ν/cm−1): 3446–3328 (N—H), 2993 (Ar—H), 1729 (C=O), 1619 (C=N), 1400–1325 (C—F), 1137–1059 (C—O—C). MS (FAB): m/e, 484 (M+).

In the second step, 5.0 mmol of ethyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carboxylate were added to 5.0 mmol of an aromatic aldehyde, and 1.0 g of 4 Å molecular sieve. Finally, 0.1 g of methylbenzenesulfonic acid was used as a catalyst, which was dissolved in 20.0 mL of toluene and heated under reflux at 120 °C for 20 h. After the reaction was completed, the reaction solution was cooled to 70 °C with suction filtration, and the filtrate was collected in a rotary flask, and 2.0 g of silica gel was added. Finally, different proportions of ethyl acetate and petroleum ether were used as developing agents. Dry loading and chromatography were performed to obtain the title compound. Yield: 1.25 g (76.0%). 1H NMR (CDCl3, 400 MHz, ppm) δ 3.75 (s, J = 7.2 Hz, 3H), 4.11 (d, J = 8.4 Hz, 2H), 6.44 (s, J = 6.8 Hz, 1H), 6.51 (s, J = 7.2 Hz, 2H), 6.76 (s, J = 7.2 Hz, 1H), 7.12 (s, J = 8.4 Hz, 1H), 7.55 (s, J = 7.2 Hz, 1H), 7.61 (s, J = 6.4 Hz, 1H). IR (KBr, ν/cm−1): 3063 (bezene ring C—H), 1729 (—C=O), 1570–1394 (benzene ring skeleton vibration), 1311 (C—F), 815 (aromatic ring C—H). MS (FAB): m/e, 602 (M+).

After allowing the Vethyl acetate/Vpetroleum ether (1:4) to stand in air for 14 days, transparent colorless 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 82.4%).

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 were allowed to rotate to best fit the experimental electron density. The ethyl group was refined with a disorder model. Atom C16 and C17 of the ethyl moiety were found to be disordered over two positions (C16/C16A and C17/C17A).

Comment

Schiff base compounds are carbon-nitrogen double bond imine compounds, which are widely used in the fields of medicine and biology, and have antiviral, bactericidal and antibacterial activities. They also play a huge role in the field of fluorescent probes and organic optoelectronics [5], [6]. Some new fipronil Schiff base derivatives have been synthesized in the early stage of this experiment and achieved good insecticidal effects. Because the ester group occupies an important position in the fields of pesticides and medicines, such as pyrethroid pesticides and pre-ester compounds, it proves that the ester compounds have good activity. Phenylpyrazoles are widely used in pesticides, such as fipronil and acetonitrile. The toxicity of phenylpyrazoles to insects and mammals can be attributed to their role as non-competitive blockers on GABA receptors, effecting the structure of GABA-gated chloride channels [7], [8], [9], [10]. Many useful organic reactions are often used in pesticide synthesis, and reasonable and innovative methods are hoped for in the “acetation, phthalamidation, and sulfophthalation” [11]. In this experiment, esterification was used to synthesize ethyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carboxylate with high yield, which is beneficial to the synthesis of title product.

The crystal structure of the title compound belongs to the space group P1̄, each unit cell is composed of 4 molecules. According to the data, in the ester group of the pyridine ring, the O(4)-C(15) bond length is with 1.210(3) Å shorter than the O(2)-C(9) bond length of 1.367(3) Å. This is because O(4)-C(15) is a carbon-oxygen double bond. N(3)-C(7) bond length is 1.280(3) Å, which is typical for a double bond. From the crystal structure, it is seen that the aryl and pyrazolyl moieties are not coplanar.

The packing of the title structure is partially facilitated by Y—X⋯π interactions between aromatic rings in neighboring molecules. The two most prominent interactions are given in the Y-X⋯Cg(π-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 each 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.

The bioactivities of the title compound 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 60 s and allowed to dry for 3 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 20 °C and 80% relative humidity under a photoperiod of 18:10 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 result showed that the activities of the title compound against Plutella xylostella after 24 h is 13.86 mg ⋅ L−1 better than that of fipronil 26.97 mg ⋅ L−1. This approach proposes a novel insight to provide a great number of novel phenylpyrazole Schiff base fluorescent insecticide by a general green method.

It is noted that 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 of the spectrum. Strong absorption peak near 221 nm and 286 nm, belonging to the conjugated absorption peak of benzene ring and pyrazole ring, in the title compound. The aryl moiety C8—C13 forms a larger conjugated structure with the pyrazolyl moiety, resulting in a red shift in UV absorption and a medium-intensity absorption peak at 332–398 nm. Its UV absorption is mainly attributed to the p-π* transition of the compound conjugated system. The fluorescene spectrum of the title compound shows a strong peak at 456 nm. Thus phenylpyrazole heterocycle are good candidates to design and develop new fluorescent pesticides, which lays a foundation for the natural degradation and fluorescence detection of pesticide residues based on the phenylpyrazole Schiff base structure.

Acknowledgements

The authors thank the National Natural Science Foundation of China (Grant Nos. 20702064, 21177161 and 31402137); the Natural Science Foundation of Hubei province for Distinguished Yong Scholars (No. 2013CFA034); the Program for Excellent Talents in Hubei Province (RCJH15001) and the Fundamental Research Funds for the Central University, South-Central University for Nationalities.

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Received: 2019-12-09
Accepted: 2020-01-31
Published Online: 2020-03-05
Published in Print: 2020-04-28

©2020 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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  43. Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one, C15H9FO3
  44. Crystal structure of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)quinolin-1-ium perchlorate – methanol (1/1), C15H16N5O5Cl
  45. The crystal structure of bis(N-(amino(pyridin-2-yl)methylene)-5-chloro-2-hydroxybenzohydrazonato-κ3N,N′,O)zinc(II) – methanol (2/5), C57H60Cl2N16O13Zn2
  46. Synthesis and crystal structure of 4,4′-di(4-pyridyl)-6,6′-di(tert-butyl)-2,2′-[propylenedioxybis(nitrilomethylidyne)]diphenol, C35H40N4O4
  47. Crystal structure of (3E,3′E)-3,3′-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(4-hydroxy-4-phenylbut-3-en-2-one), C22H18N2O4S3
  48. Crystal structure of (N-benzyl-N-methyl-dithiocarbamato-κ2S,S′)di(4-chlorobenzyl)chloridotin(IV), C23H22Cl3NS2Sn
  49. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) sodium bromide hydrate, [Na(18-crown-6)]Br ⋅ H2O, C12H26BrNaO7
  50. Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4
  51. Crystal structure of chlorido (2-(4-ethylphenyl)pyrimidine-k2C,N)(triphenylphosphane-kP) palladium(II), C30H26ClN2PPd
  52. Crystal structure of 18-crown-6 – 1,4-diiodotetrafluorobenzene – acetonitrile (1/1/2), C22H30F4I2N2O6
  53. Crystal structure of diisobutyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C16H24O6
  54. Crystal structure of poly[[tris(μ2-cis-1,2-cyclohexanedicarboxylato)-κ2O, O′]-bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N, N′,N′′]-trizinc(II)] – water (1/20), C60H106N12O32Zn3
  55. The synthesis and crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxamide–tetrahydrofuran (1/1), C16H14N4Cl2F6O3S
  56. Crystal structure of dimethylbis(diisopropyldithiocarbamato-κ2S,S′)tin(IV), C16H34N2S4Sn
  57. Crystal structure of diisopropyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C14H20O6
  58. The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
  59. The crystal structure of a matrine derivative, 13-(methylamine-1-yl) carbodithioate matrine, C17H27N3OS2
  60. Crystal structure of bis(2-hydroxy-6-((phenylimino)methyl)phenolato-κ2N,O)copper(II), C26H20CuN2O4
  61. The crystal structure of 2-p-fluorophenyl-5-dihydroxymethyl-1,3,4-oxadiazole, C9H7FN2O3
  62. Crystal structure of dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV), C24H16Cl4N2Sn
  63. Crystal structure of bis{bromido-triphenyltin(IV)}(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′), C46H38Br2N2O2Sn2
  64. Crystal structure of 2-(5-chloro-quinolin-8-yloxy)-N-quinolin-8-yl-acetamide, C20H14N3O2Cl
  65. Crystal structure of bis(N-(1-(3-ethylpyrazin-2-yl)ethylidene)-3-hydroxy-2-naphthohydrazonato-κ3N,N′,O)cobalt(II) — dimethylformamide (1/1), C41H41N9O5Co
  66. Crystal structure of bis[2-(1-(3-ethylpyrazin-2-yl)ethylidene)-1-tosylhydrazin-1-ido-κ3-N,N′,O]copper(II), C30H34N8O4S2Cu
  67. Crystal structure of (2-p-tolylpyrimidine-κ2C,N)(triphenylphosphane-κP) palladium(II), C29H24ClN2PPd
  68. Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8
  69. The synthesis and crystal structure of N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide, C20H10N4Cl2F6O2S
  70. The crystal structure of 4-(trifluoromethyl)nicotinic acid, C7H4F3NO2
  71. Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS
  72. The crystal structure of 2,2,2-trifluoro-1-(isoquinolin-1-yl)ethane-1,1-diol, C11H8F3NO2
  73. The crystal structure of 3-bromoisonicotinic acid, C6H4BrNO2
  74. The crystal structure of 5-nitropicolinic acid monohydrate, C6H6N2O5
  75. The crystal structure of 3-(4-hydroxybenzyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H18O5
  76. Crystal structure of [[Mo3Se7(S2CNEt2)3]2(μ-Se)] ⋅ 2(C6H4Cl2), C42H68Cl4Mo6N6S12Se15
  77. Crystal structure of (E)-4-hydroxy-3-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)pent-3-en-2-one, C13H12N2O3S
  78. The crystal structure of (2,3-dioxo-5,6:13,14-dibenzo-9,10-benzo-1,4,8,11-7, 11-diene-κ4N,N′,N′′,N′′′)-nickel(II), Ni(C22H14N4O2)
  79. Crystal structure of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid, C15H17N3O4S
  80. The crystal structure of dichlorobis(2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl) palladium(II)-dichloroform, C68H100Cl8P2Pd
  81. Crystal structure and antimicrobial properties of (1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium(I) pentaiodide, C16H32CsI5O8
https://doi.org/10.1515/ncrs-2019-0898
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of catena-poly[(μ2-3-(benzo[d]thiazol-2-yl)-5-carboxybenzoato-κ2N:O)silver(I)], C15H8AgNO4S
  3. Crystal structure of bis(4-phenylpiperazin-1-ium) bis(2-(4-phenylpiperazin-1-yl)succinato-κ2O,O′)copper(II) tetrahydrate, C48H70CuN8O12, [C10H14N2]2[Cu(C14H17N2O4)2] ⋅ 4 H2O
  4. Crystal structure of triaqua-bis(2-(6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)-1-(2-oxo-2,5-dihydrofuran-3-yl)ethane-1-sulfonato-κ2O,O′)calcium(II) – ethanol (1/2), C44H76CaO19S2
  5. The crystal structure of ethyl 5-(4-(diphenylamino)phenyl)thiophene-2-carboxylate, C25H21NO2S
  6. The crystal structure of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, C7H6BrN5
  7. The crystal structure of (E)-5-chloro-2-hydroxy-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide, C15H13ClN2O4
  8. The crystal structure of (2Z,2′Z)-N′,N′′′′-(pyridine-2,6-dicarbonyl)dipicolinohydrazonamide, C19H17N9O2
  9. Photochromic properties and crystal structure of 3,3′-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-(4-(azidomethyl)phenyl)-2-methylthiophene), C29H20F6N6S2
  10. Crystal structure of aqua-dichlorido-(4-(((3-ethoxy-2-oxidobenzylidene)hydrazono)(oxido)methyl)pyridin-1-ium-κ3N,O,O′)iron(III), C15H16Cl2N3O4Fe
  11. Crystal structure of catena-poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)-bis(2,3,4,5-tetrabromo-6-carboxybenzoato-κ1O)-nickel(II)], C26H14Br8NiN2O10
  12. Crystal structure of diethanol-κ1O-bis(μ2-N-((2-oxidonaphthalen-1-yl)methylene)pyrazine-2-carbohydrazonato-κ5N,O,O′:O′:N′)-bis(nitrato-κ2O,O′)dieuropium(III), C36H32N10O12Eu2
  13. The crystal structure of 2-aminoisophthalic acid, C8H7NO4
  14. Crystal structure of (E)-2-(4-((3,4-difluorobenzyl)oxy)styryl)-4,6-dimethoxybenzaldehyde, C24H20F2O4
  15. Crystal structure of 2-benzoylpyrene, C23H14O
  16. Crystal structure of chlorido-(η6-p-cymene)-(N-(2-fluorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) – acetone (1/1), C22H23ClN2F7OPRu
  17. The crystal structure of 2-bromoisonicotinic acid, C6H4BrNO2
  18. Crystal structure of 1,3,5,7-tetraphenyl-8-(N-phenylformamido)-2-oxa-5-azabicyclo[4.2.0]oct -3-en-7-yl benzoate, C44H34N2O4
  19. Synthesis and crystal structure of 4-(3-acetyl-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one, C21H21N3O4S
  20. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)-(μ2-3,4,5,6-tetrafluorophthalato-κ2O:O′)nickel(II)], C18H12F4NiN2O6
  21. Crystal structure of 4-hydroxynaphtho[2,3-b]benzofuran-6,11-dione, C16H8O4
  22. The crystal structure of 3,10-bis(4-methoxyphenyl)-6,12-dibenzyl-2,9-acetyl-6,12-diazapentacyclo[6.3.1.02,7.04,11.05,9]dodecane – acetone (1/1), C45H48N2O5
  23. The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C17H15N2BrO
  24. Crystal structure of catena-poly[diaqua-(μ2-oxalyl dihydrazide-κ4N,O:N′,O′)-bis(μ2-pyridine-2,3-dicarboxylato-κ3N,O,O′)dicadmium(II)] hexahydrate, C16H28O18N6Cd2
  25. Crystal structure of poly[tetra-(μ4-naphthalene-1,8-dicarboxylato-κ4O:O,O′: O′′:O′′,O′′′)-(μ4-oxo-κ4O:O:O:O) penta-lead(II)], C48H24O17Pb5
  26. Crystal structure of 5H-dibenzo[c,f][1,5]oxabismocin-12 (7H)-yl acetate, C16H15O3Bi
  27. The crystal structure of 2-(4-chloro-6-nitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide, C12H6Cl2N4O5
  28. Crystal structure of bis(3-methyl-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)nickel(II), C28H26N8O2Ni
  29. Crystal structure of 3,10-bis(4-chlorophenyl)-6,12-dibenzyl-2,9-acetyl-6,12-diazapentacyclo[6.3.1.02,7.04,11.05,9]-dodecane, C40H36Cl2N2O2
  30. Crystal structure of bis[(μ2-4⋯O,O′:O′)-(4-hydroxybenzoato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)]-di-lead(II)μ-4-hydroxybenzoato-κ3O,O′:O′;κ3O,O′:O′-bis-[(4-hydroxybenzoato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)di-lead(II)] monohydrate, C52H36N4O12Pb2 ⋅ H2O
  31. Crystal structure of poly[diaqua-(μ3-3,4,5,6-tetrafluoro-phthalato-κ3O:O′:O′′)-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)cobalt(II)], C14H9CoF4NO6
  32. Crystal structure of 7-hydroxy-4-phenyl-2H-chromen-2-one, C15H10O3
  33. Crystal structure of 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione 4-hydroxybenzoic acid, C20H24N4O6
  34. Crystal structure of catena-poly[(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)-bis(nitrato-κ1O)zinc(II)], C17H16N6O7Zn
  35. The crystal structure of diaqua-bis(6-aminopicolinato-κ2N,O)magnesium(II), C12H14O6N4Mg
  36. Crystal structure of (pyridine-2-carboxamide-κ2N,O)-[tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′]nickel(II) diperchlorate — methanol (1/3), C33H39Cl2N9NiO12
  37. Crystal structure of catena-poly[diaqua-bis(3-(4-trifluoromethyl-phenyl)-acrylato-κO1)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N3:N3′)cobalt(II)], C32H26CoF6N4O6
  38. Crystal structure of (E)-3-(2-(2-hydroxy-4-methoxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate monohydrate, C22H25NO5S⋅H2O
  39. The crystal structure of bis(N-oxy-2-(1H-tetrazol-1-yl) acetamide κ2O,O′)-diaqua-zinc(II), C6H12ZnN10O6
  40. Crystal structure of (E)-4-((4-chlorophenylimino)methyl)pyridinium 3,5-dinitrobenzoate, C19H13ClN4O6
  41. Crystal structure of dichlorido-bis((E)-2-((pyridin-4-ylmethylene)amino)phenol)zinc(II), C24H20Cl2N4O2Zn
  42. Crystal structure of cyclo-[tetrachlorido-bis(μ2-p-xylylenediamine-κ2N:N′)dipalladium(II)] dimethyl sulfoxide solvate, C20H36Cl4N4O2Pd2S2
  43. Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one, C15H9FO3
  44. Crystal structure of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)quinolin-1-ium perchlorate – methanol (1/1), C15H16N5O5Cl
  45. The crystal structure of bis(N-(amino(pyridin-2-yl)methylene)-5-chloro-2-hydroxybenzohydrazonato-κ3N,N′,O)zinc(II) – methanol (2/5), C57H60Cl2N16O13Zn2
  46. Synthesis and crystal structure of 4,4′-di(4-pyridyl)-6,6′-di(tert-butyl)-2,2′-[propylenedioxybis(nitrilomethylidyne)]diphenol, C35H40N4O4
  47. Crystal structure of (3E,3′E)-3,3′-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(4-hydroxy-4-phenylbut-3-en-2-one), C22H18N2O4S3
  48. Crystal structure of (N-benzyl-N-methyl-dithiocarbamato-κ2S,S′)di(4-chlorobenzyl)chloridotin(IV), C23H22Cl3NS2Sn
  49. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) sodium bromide hydrate, [Na(18-crown-6)]Br ⋅ H2O, C12H26BrNaO7
  50. Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4
  51. Crystal structure of chlorido (2-(4-ethylphenyl)pyrimidine-k2C,N)(triphenylphosphane-kP) palladium(II), C30H26ClN2PPd
  52. Crystal structure of 18-crown-6 – 1,4-diiodotetrafluorobenzene – acetonitrile (1/1/2), C22H30F4I2N2O6
  53. Crystal structure of diisobutyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C16H24O6
  54. Crystal structure of poly[[tris(μ2-cis-1,2-cyclohexanedicarboxylato)-κ2O, O′]-bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N, N′,N′′]-trizinc(II)] – water (1/20), C60H106N12O32Zn3
  55. The synthesis and crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxamide–tetrahydrofuran (1/1), C16H14N4Cl2F6O3S
  56. Crystal structure of dimethylbis(diisopropyldithiocarbamato-κ2S,S′)tin(IV), C16H34N2S4Sn
  57. Crystal structure of diisopropyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C14H20O6
  58. The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
  59. The crystal structure of a matrine derivative, 13-(methylamine-1-yl) carbodithioate matrine, C17H27N3OS2
  60. Crystal structure of bis(2-hydroxy-6-((phenylimino)methyl)phenolato-κ2N,O)copper(II), C26H20CuN2O4
  61. The crystal structure of 2-p-fluorophenyl-5-dihydroxymethyl-1,3,4-oxadiazole, C9H7FN2O3
  62. Crystal structure of dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV), C24H16Cl4N2Sn
  63. Crystal structure of bis{bromido-triphenyltin(IV)}(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′), C46H38Br2N2O2Sn2
  64. Crystal structure of 2-(5-chloro-quinolin-8-yloxy)-N-quinolin-8-yl-acetamide, C20H14N3O2Cl
  65. Crystal structure of bis(N-(1-(3-ethylpyrazin-2-yl)ethylidene)-3-hydroxy-2-naphthohydrazonato-κ3N,N′,O)cobalt(II) — dimethylformamide (1/1), C41H41N9O5Co
  66. Crystal structure of bis[2-(1-(3-ethylpyrazin-2-yl)ethylidene)-1-tosylhydrazin-1-ido-κ3-N,N′,O]copper(II), C30H34N8O4S2Cu
  67. Crystal structure of (2-p-tolylpyrimidine-κ2C,N)(triphenylphosphane-κP) palladium(II), C29H24ClN2PPd
  68. Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8
  69. The synthesis and crystal structure of N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide, C20H10N4Cl2F6O2S
  70. The crystal structure of 4-(trifluoromethyl)nicotinic acid, C7H4F3NO2
  71. Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS
  72. The crystal structure of 2,2,2-trifluoro-1-(isoquinolin-1-yl)ethane-1,1-diol, C11H8F3NO2
  73. The crystal structure of 3-bromoisonicotinic acid, C6H4BrNO2
  74. The crystal structure of 5-nitropicolinic acid monohydrate, C6H6N2O5
  75. The crystal structure of 3-(4-hydroxybenzyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H18O5
  76. Crystal structure of [[Mo3Se7(S2CNEt2)3]2(μ-Se)] ⋅ 2(C6H4Cl2), C42H68Cl4Mo6N6S12Se15
  77. Crystal structure of (E)-4-hydroxy-3-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)pent-3-en-2-one, C13H12N2O3S
  78. The crystal structure of (2,3-dioxo-5,6:13,14-dibenzo-9,10-benzo-1,4,8,11-7, 11-diene-κ4N,N′,N′′,N′′′)-nickel(II), Ni(C22H14N4O2)
  79. Crystal structure of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid, C15H17N3O4S
  80. The crystal structure of dichlorobis(2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl) palladium(II)-dichloroform, C68H100Cl8P2Pd
  81. Crystal structure and antimicrobial properties of (1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium(I) pentaiodide, C16H32CsI5O8
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