Home The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
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The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S

  • Lianqing Chen EMAIL logo and Xiaoshan Wei
Published/Copyright: May 8, 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

C18H15N3Cl2F6O3S, monoclinic, P21/n (no. 14), a = 5.6682(7) Å, b = 31.130(4) Å, c = 12.2829(16) Å, β = 98.328(2)°, V = 2144.5(5) Å3, Z = 4, Rgt(F) = 0.0535, wRref(F2) = 0.1133, T = 173 K.

CCDC no.: 1908255

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:0.13 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.48 mm−1
Diffractometer, scan mode:CCD,
θmax, completeness:27.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:12742, 4881, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3550
N(param)refined:326
Programs:CrysAlisPRO [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.18202(14)0.19273(3)0.64316(6)0.0313(2)
Cl20.84484(14)0.22254(3)0.38067(7)0.0313(2)
S10.61958(13)0.36151(2)0.64006(6)0.02034(17)
F11.0614(3)0.33309(6)0.64888(16)0.0382(5)
F20.9362(3)0.36871(7)0.50270(16)0.0461(5)
F31.0286(4)0.40138(7)0.6569(2)0.0543(6)
F4a0.510(3)0.0451(4)0.5346(11)0.074(3)
F5a0.8119(17)0.0568(2)0.4524(8)0.065(2)
F6a0.465(3)0.05585(19)0.3623(6)0.098(4)
O10.6526(4)0.34991(7)0.75781(16)0.0297(5)
O20.4073(4)0.38274(6)0.40977(16)0.0248(5)
O30.2380(4)0.33638(6)0.28040(16)0.0266(5)
N10.4832(4)0.24747(7)0.51708(17)0.0166(5)
N20.3834(4)0.27019(7)0.42658(18)0.0185(5)
N30.7045(4)0.25739(8)0.69439(18)0.0216(5)
H3A0.7154360.2300510.7042930.026*
H3B0.7685260.2746410.7449940.026*
C10.3760(5)0.17380(9)0.5587(2)0.0206(6)
C20.5093(5)0.20246(8)0.5064(2)0.0160(6)
C30.4209(5)0.31064(9)0.4548(2)0.0165(6)
C40.5477(5)0.31509(8)0.5628(2)0.0179(6)
C50.9276(5)0.36590(11)0.6095(3)0.0297(7)
C60.5881(5)0.27311(9)0.6006(2)0.0171(6)
C70.3420(5)0.34381(9)0.3711(2)0.0195(6)
C80.3675(6)0.41964(10)0.3361(2)0.0306(8)
H80.2339470.4135000.2755160.037*
C90.3036(6)0.45674(10)0.4040(3)0.0376(8)
H9A0.4255380.4598580.4698660.045*
H9B0.1482150.4511080.4290250.045*
C100.2886(8)0.49820(12)0.3374(4)0.0546(11)
H10A0.1544520.4961960.2763210.066*
H10B0.2561030.5224930.3851040.066*
C110.5163(8)0.50680(11)0.2911(3)0.0482(10)
H11A0.6472870.5120300.3522290.058*
H11B0.4967720.5329690.2448710.058*
C120.5812(9)0.46943(13)0.2228(3)0.0592(12)
H12A0.7370440.4750870.1981860.071*
H12B0.4599880.4664220.1566590.071*
C130.5955(7)0.42782(11)0.2887(3)0.0455(10)
H13A0.6253520.4035480.2404880.055*
H13B0.7307780.4294670.3493770.055*
C140.6715(5)0.18680(9)0.4409(2)0.0196(6)
C150.6964(6)0.14327(9)0.4250(2)0.0262(7)
H150.8065760.1326740.3800610.031*
C160.5564(6)0.11536(9)0.4762(2)0.0281(7)
C170.5739(9)0.06817(12)0.4567(3)0.0488(10)
C180.3985(6)0.13011(9)0.5430(2)0.0264(7)
H180.3057720.1104050.5779840.032*
F6Ab0.714(6)0.0550(6)0.405(3)0.081(6)
F4Ab0.341(4)0.0544(6)0.402(3)0.082(6)
F5Ab0.561(7)0.0451(11)0.549(2)0.050(5)

  1. aOccupancy: 0.73(3), bOccupancy: 0.27(3).

Source of material

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

Fipronil (systematic name: 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile, 4.55 g, 10 mmol) was dissolved in 30 mL cyclohexanol solution, and anhydrous ferric chloride (3.24 g, 20 mmol) was added portionwise. After ultrasonic stirring for 0.5 h, the reaction mixture was reacted at 100 °C for 9 h. The reaction solution was cooled to room temperature, and replaced with a distillation apparatus to remove excess solvent to obtain a brown paste. Distilled water (100 mL) and ethyl acetate (500 mL) were successively added to the tan paste, and then extracted three times to combine the organic phases. After drying over MgSO4, the mixture was filtered, and the filtrate was concentrated by rotary evaporation and applied to the activated silica powder (5.0 g). The crude product was isolated by column chromatography, the crude material was washed several times with petroleum ether, filtered and dried to give the title compound. Yield: 3.10 g (68.1%), 1H NMR (CDCl3, 400 MHz, ppm) δ 7.79 (s, 2H, Ar—H), 5.16 (s, 2H, C—NH2), 5.02 (dd, J = 12.4, 7.6 Hz, 1H, C—CH), 1.99 (s, 2H, C—CH2), 1.77 (s, 2H, C—CH2), 1.58−1.47 (m, 2H, C—CH2), 1.43−1.31 (m, 2H, C—CH2), 1.28 (d, J = 12.0 Hz, 2H, C—CH2). IR (KBr, ν, cm−1): 3451 and 3333 (N—H stretching vibration), 2947 (C—H), 1725 (C=O), 1618 (C=N), 1454 and 1401 (benzene ring skeleton vibration), 1325 (C—F), 1141 and 1064 (C—O—C), 874 and 817(aromatic ring C—H). MS (FAB): m/e, 537 (M+).

After allowing the Vethyl acetate/Vpetroleum ether (1:3) to stand in air for 10 days, transparent block colorless crystals formed by slowly evaporating of the solvent. The crystals of the title compound were isolated, washed with light petroleum and dried in vacuum (yield 82.3%)

Experimental details

All H atoms are geometrically positioned and refined using the riding model. The C—H constraint distance is from 0.95 Å to 1.00 Å, and Uiso(H) is limited to 1.5 Uiso(C) methyl H atoms and 1.2 Ueq(C) are aryl H atoms, allowing the rotation of the C—C bond. The CF3 group was refined by a disordered model. It was found that the atoms F4, F5 and F6 of the CF3 moiety were disordered at three positions (F4/F4A, F5/F5A and F6/F6A) and split into two positions with occupancies of 0.728 and 0.272 and refined anisotropically.

Comment

Phenylpyrazole derivatives have attracted increasing attention owing to their excellent biological activities and play a fundamental role in the rapid development of pesticides [5]. Fipronil is the first commercial phenylpyrazole insecticide introduced for pest control, 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]. Its mechanism of action is to inhibit insecticidal α-amino butyric acid, thereby blocking the gated chloride channel to kill insects [7]. Ester compounds are of great significance in the field of medicinal chemistry, especially ester prodrugs have high stability, long duration of action, good solvent and low toxic side effects [8]. However, there was very few phenylpyrazole ester derivatives reported, and it still remains a great challenge to find some novel phenylpyrazole ester pesticides [9]. There is an urgent need to design and develop a general green approach to provide more luminescent phenylpyrazole ester insecticides.

The core structure of the title molecule consists of a pyrazole ring. A trifluoromethanesulfinyl group and a cyclohexyl ester group are linked on the peripheral part, and a phenyl ring, which is bridged to the pyrazole ring with N1—C2 bond 1.417(3) Å. The bond distances of C17—F4, C17—F5 and C17—F6 (CF3 groups attached to the phenyl moiety) are 1.290(12) Å, 1.403(9) Å and 1.291(6) Å, respectively and their average bond distance is slightly shorter than the average value of the other CF3 group in the trifluoromethanesulfinyl moiety. The S1—C4 bond distance is 1.744(3) Å, significantly larger than the double bond length of S1—O1 (1.476(2) Å), which is the single bond connecting 5-membered heterocyclic pyrazole ring [10]. The bond length of O3—C7 is 1.205(3) Å, which is shorter than the bond length of O2—C8, 1.460(3) Å. In the crystal structure of title compound, the 2,6-dichloro-4-(trifluoromethyl)phenyl ring is twisted out of the plane of pyrazole ring and the two heterocyclic rings makes a dihedral angle of 74.53(2)°. The ester group is coplanar to the plane of pyrazole ring. However, CF3 group in the trifluoromethanesulfinyl moiety is almost perpendicular to the pyrazole plane and the angle of C4—S1—C5 is 95.97(14)° [11]. The N2—C3 bond distance is 1.315(3) Å, which is the shortest carbon-nitrogen bond.

The packing of the title structure is partially facilitated by π–π conjugated interactions between aromatic rings in neighboring molecules. The two most prominent such interactions are given in the π–π ones (Cg1 represents the pyrazole ring N1/N2/C3/C4/C6, Cg2 that of C1/C2/C14/C15/C16/C18) benzene ring. The first of these interactions, C(g)1⋯C(g)1 acts in centrosymmetric pairs between two aromatic rings of neighboring molecules, connecting the molecules to infinite chains along the a axis of the unit cell. The second C(g)2⋯C(g)2 π–π interaction connects these chains with each other. There are no classic H-bonds.

The bioactivities of the title compound and fipronil against the 3rd instar larvae of Plutella xylostella were investigated 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 2.8 h. The treated leaf discs were placed into Petri dishes (10.0 cm diameter). Then, 15 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 26 °C and 86% relative humidity under a photoperiod of 15:9 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 exhibited that the activities of the title compound against Plutella xylostella after 24 h is 17.28 mg⋅L−1 which is slightly better than that of fipronil 27.45 mg⋅L−1. This result proposes a novel insight to provide more novel phenylpyrazole ester pesticides by a general green method.

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 National Natural Science Foundation of China (Grant Nos. 20702064, 21177161 and 31402137); Natural Science Foundation of Hubei province for Distinguished Young Scholars (No. 2013CFA034); 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).

References

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Received: 2019-02-28
Accepted: 2019-04-05
Published Online: 2019-05-08
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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  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-2019-0148
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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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