Home The synthesis and crystal structure of isobutyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C16H13Cl2F6N3O3S
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The synthesis and crystal structure of isobutyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C16H13Cl2F6N3O3S

  • Lianqing Chen ORCID logo EMAIL logo and Yanting Du
Published/Copyright: June 19, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 5

Abstract

C16H13Cl2F6N3O3S, monoclinic, P21/n (no. 14), a = 5.8650(10) Å, b = 30.196(5) Å, c = 11.777(2) Å, β = 96.619(2)°, V = 2071.8(6) Å3, Z = 4, Rgt(F) = 0.0521, wRref(F2) = 0.1211, T = 173 K.

CCDC no.: 1920921

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:0.12 × 0.10 × 0.07 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.49 mm−1
Diffractometer, scan mode:CCD, φ and ω-scans
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:15720, 4233, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3370
N(param)refined:282
Programs:Bruker [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.04011(14)0.77877(3)0.63055(7)0.0316(2)
Cl20.70487(13)0.80621(3)0.36042(7)0.0363(2)
S10.25821(12)0.63290(2)0.37233(6)0.01874(17)
F1−0.1676(3)0.66337(7)0.36723(18)0.0433(5)
F2−0.0452(3)0.62899(7)0.52224(16)0.0417(5)
F3−0.1378(4)0.59258(8)0.3664(2)0.0566(6)
F40.3827(7)0.96016(8)0.4564(2)0.0917(11)
F50.3646(7)0.95215(8)0.6342(2)0.1048(13)
F60.0659(7)0.94870(9)0.5147(3)0.1043(12)
O10.2263(4)0.64386(7)0.24872(16)0.0268(5)
O20.4919(3)0.61221(6)0.61135(16)0.0216(4)
O30.6658(3)0.66245(7)0.73301(16)0.0235(5)
N10.3989(4)0.75131(7)0.49104(18)0.0154(5)
N20.5007(4)0.72835(8)0.58411(18)0.0165(5)
N30.1727(4)0.74014(8)0.31342(19)0.0208(5)
H3A0.1619850.7682210.3023370.025*
H3B0.1069850.7221210.2633370.025*
C10.2111(5)0.81497(10)0.5649(2)0.0194(6)
C20.3750(4)0.79788(9)0.5002(2)0.0158(6)
C30.4624(4)0.68636(9)0.5581(2)0.0152(5)
C40.3317(4)0.68134(9)0.4490(2)0.0154(6)
C5−0.0389(6)0.63015(11)0.4100(3)0.0306(7)
C60.2918(4)0.72429(9)0.4091(2)0.0160(6)
C70.5530(5)0.65337(9)0.6443(2)0.0168(6)
C80.5814(5)0.57675(10)0.6884(3)0.0260(7)
H8A0.5289950.5808840.7646610.031*
H8B0.7513230.5770590.6973540.031*
C90.4942(6)0.53363(10)0.6377(3)0.0325(8)
H90.5356560.5321410.5577670.039*
C100.6128(7)0.49519(11)0.7045(3)0.0429(9)
H10A0.7792950.4977100.7040120.064*
H10B0.5595220.4671420.6689810.064*
H10C0.5759120.4960210.7835720.064*
C110.2373(7)0.52951(14)0.6321(5)0.0660(14)
H11A0.1914100.5320690.7092730.099*
H11B0.1889950.5006520.5997030.099*
H11C0.1642580.5531300.5837440.099*
C120.5094(5)0.82674(10)0.4451(2)0.0216(6)
C130.4847(6)0.87218(10)0.4564(3)0.0294(7)
H130.5784750.8920760.4199550.035*
C140.3209(6)0.88800(10)0.5219(3)0.0308(8)
C150.2889(10)0.93731(13)0.5339(3)0.0560(12)
C160.1830(6)0.85995(10)0.5763(2)0.0260(7)
H160.0710640.8714110.6206380.031*

Source of material

All chemical reagents and solvents including fipronil were of analytical grade quality, which were obtained from commercial suppliers and used directly without further purification (Wuhan Guoyao Chemical Reagent Co., Ltd.). The synthesis process of the target product involves the following steps by an improved Pinner reaction. Firstly, to a 250 mL three-necked bottle, added 0.01 mol (4.37 g) fipronil and then dissolved by 30 mL isobutyl alcohol, 0.02 mol of anhydrous ferric chloride in batches was added as a catalyst, ultrasonic stirring for 0.5 h, the reaction mixture was reacted at 100 °C for 9 h. The resulting solution was then cooled to room temperature, and removed excess solvent to give a tan cream. Secondly, 100 mL of distilled water and 50 mL of ethyl acetate were added to the tan cream one by one, and extracted three times. The organic phases were combined and washed with saturated sodium carbonate solution (30 mL), distilled water and brine, respectively, and then dried over MgSO4. The filtrate was concentrated, swirled and adsorbed onto 6 g of activated silica gel. Finally, the crude product was obtained by column chromatography on silica gel with Vethyl acetate/Vpetroleum ether (1:4) the eluent, which was dried under vacuum to give the title compound. Yield: 91.2%, 1H NMR (CDCl3, 400 MHz, ppm) δ 7.79 (s, 2H, Ar—H), 5.17 (s, 2H, C—NH2), 4.15 (d, J = 8.0 Hz, 2H, C—CH2), 2.08 (td, J = 20.0, 12.0 Hz, 1H, C—CH), 0.99 (dd, J = 8.0, 8.0 Hz, 6H, C—CH3). IR (KBr, ν, cm−1): 3451, 3328 (N—H), 2970 (Ar—H), 1728 (C=O), 1618 (—C=N), 1497 (benzene ring skeleton vibration), 1326 (C—F), 1144, 1065 (C—O—C), 875, 816 (C—H), 657 (aromatic ring C—H). MS (FAB): m/e, 512 (M+).

After allowing the Vethyl acetate/Vpetroleum ether (1:5) to stand in air for 8 days, transparent colorless block crystals of the title compound formed by slow evaporation of the solvent. The crystals were isolated, washed with light petroleum and dried in vacuum (yield 89.6%).

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 and nitrogen H atoms and 1.5 Ueq for the methyl H atoms. The special instructions are as follows:

  1. Fixed Uiso,

    At 1.2 times of: All C(H) groups, All C(H, H) groups, All N(H, H) groups

    At 1.5 times of: All C(H, H, H) groups

  2. Riding coordinates: N3(H3A, H3B)

  3. Ternary CH refined with riding coordinates: C9(H9)

  4. Secondary CH2 refined with riding coordinates: C8(H8A, H8B)

  5. Aromatic/amide H refined with riding coordinates: C13(H13), C16(H16)

  6. Idealised Me refined as rotating group: C10(H10A, H10B, H10C), C11(H11A, H11B, H11C).

Comment

Phenylpyrazole derivatives have attracted increasing attention owing to their excellent biological activities [5]. In the field of pesticides, they play a fundamental role in the rapid development of insecticides, and in the field of medicine, their derivatives can reduce analgesia and inflammation [6]. In the agricultural field, phenylpyrazole compounds are mainly used to deal with soil insects such as gold nematodes, aquatic insects such as rice, and control of aphids [7]. In addition, phenylpyrazole heterocycle derivatives are useful inter-mediates and ligands, from which many macrocyclic compounds with high fluorescence quantum yield and supermolecular structures with extended conjugated aromatic system can be constructed. Heterocyclic ester derivatives and its complexes are important chemical reagents, which can act as a foundational role of a wide range of applications in the fields of catalysis, biochemistry, functional materials, medicine and other research areas [8]. However, to our best knowledge, only a few phenylpyrazole ester compounds have been reported. Considering on the advantages of high stability, long duration of action, good solubility and small side effects for phenylpyrazole ester derivatives, the title compound has been synthesized by an improved Pinner reaction using FeCl3 as green catalyst, and isobutyl alcohol as solvent and reactant [9].

The molecular structure consists of a pyrazole ring, including a trifluoromethanesulfinyl group and carboxylic acid isobutyl ester group linked on the peripheral part, and a phenyl ring, which is bridged with C—N bond 1.418(3) Å formed by N1—C2 single bond to the 2,6-dichloro-4-trifluoromethylphenyl moiety. The S1—C4 bond distance is 1.747(3) Å, significantly longer than the double bond length of S1—O1 (1.484(2) Å), which is the single bond connecting 5-membered heterocyclic pyrazole ring. The 2,6-dichloro-4-(trifluoromethyl)phenyl moiety is twisted out of the plane of pyrazole ring and the two heterocyclic rings makes a dihedral angle of 73.38(3)° [10]. The isobutylate group is coplanar to the plane of pyrazole ring due to the carboxyl planar structure. However the CF3 group in the trifluoromethanesulfinyl moiety is almost perpendicular to the pyrazole plane and the angle of C4—S1—C5 is 95.56(14)° [11]. The N2—C3 bond distance is 1.318(4) Å, which is the shortest carbon-nitrogen double bond. The C5—F1, C5—F2 and C5—F3 bond distance (CF3 group connecting with phenyl moiety) are 1.320(4) Å, 1.327(4) Å and 1.349(4) Å, respectively and their average bond distance is slightly larger than the average value of the other CF3 group in the trifluoromethanesulfinyl moiety. Generally the geometric parameters are similar to fibronil [12].

There are some non-classical hydrogen bonds in the packing crystal structure of the title compound, which is partially facilitated by F—H interactions between neighboring molecules. The two most prominent F—H interactions are F2—H11C (bond distance 2.660(2) Å) and F3—H11B (bond distance 2.8640(25) Å), which acts in centrosymmetric pairs between adjacent molecules, connecting these molecules to chains along the b axis of the unit cell. The other hydrogen bond F4—H10C has 2.8787(29) Å bond distance along the c axis and connects these chains with each other. The F—H interactions F1—H3B (bond distance 2.7735(21) Å) is along the a axis, working with other three kinds of hydrogen bonds and building up a perfect two-dimensional structure.

The bioactivities of the title compound and model phenylpyrazole insecticide (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. Two kinds of compounds were dissolved in organic solvent (acetone) and suspended in distilled water containing Triton X-100. Leaf discs were dipped in each test solution for 35 s and allowed to dry for 2.5 h. The treated leaf discs were placed into 10 cm diameter Petri dishes. 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 24 °C and 80% 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 determined. LC50 value was calculated by the SPSS. Bioactivity result exhibited that the activities of the title compound against Plutella xylostella after 24 h is 15.26 mg⋅L−1, better than that of fipronil 27.24 mg⋅L−1. These researches propose a novel insight to provide some novel phenylpyrazole insecticide by an improved pinner reaction.

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 Nos. 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: 2019-02-23
Accepted: 2019-06-05
Published Online: 2019-06-19
Published in Print: 2019-09-25

©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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  55. Crystal structure of 2-(3-methoxyphenyl)-3-((phenylsulfonyl)methyl)imidazo[1,2-a]pyridine, C21H18N2O3S
  56. Crystal structure of [(2-(2-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) perchlorate, C29H50Cl2N4NiO8
  57. Crystal structure of (Z)-6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-(quinoxalin-2-ylmethylene)hydrazinyl)-2,3-dihydroinden-1-one, C35H35N7O
  58. 5-Methyl-N′-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide, C22H22N8O2
  59. Crystal structure of 2,3-dichloro-6-methoxyquinoxaline, C9H6Cl2N2O
  60. Synthesis and crystal structure of 7-chloro-2-(ethylsulfinyl)-6-fluoro-3-(1H-pyrazole-1-yl)-4H-thiochromen-4-one, C13H10FN3OS2
  61. Crystal structure of 4-ethylpiperazine-1-carbothioic dithioperoxyanhydride, C14H26N4S4
  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
https://doi.org/10.1515/ncrs-2019-0137
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of poly[diaqua-(μ8-1,1′:2′,1′′-terphenyl-3,3′′,4′,5′-tetracarboxylato-κ8O1:O2:O3:O4:O5:O6:O7:O8)dicopper(II)], C22H14Cu2O10
  3. Crystal structure of 2-((1H-benzo[d]imidazol-2-ylimino)methyl)-4,6-di-tert-butylphenol, C22H27N3O
  4. Crystal structure of (4-ethoxynaphthalen-1-yl)(furan-2-yl)methanone, C17H14O3
  5. Crystal structure of 1-nonylpyridazin-1-ium iodide, C13H23N2I
  6. Crystal structure of bis[diaqua(1,10-phenanthroline-κ2N, N′)-copper(II)]diphenylphosphopentamolybdate dihydrate, C36H38Cu2Mo5N4O27P2
  7. The crystal structure of tetrakis(imidazole)-copper(I) hexafluorophosphate, C12H16CuF6PN8
  8. The crystal structure of dimethyl ((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)phosphonate, C23H33O4P
  9. Crystal structure of diaqua-bis(1,10-phenanthroline κ2N,N′)nickel(II) trifluoroacetate- trifluoroacetic acid (1/1), C30H21F9N4NiO8
  10. Crystal structure of 2-(naphthalen-2-yl)-1,8-naphthyridine, C18H12N2
  11. Synthesis and crystal structure of a new polymorph of diisopropylammonium trichloroacetate, C8H16Cl3NO2
  12. Crystal structure of dimethanol-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)cadmium(II) C34H34CdN12O2S2
  13. Crystal structure of ethyl 2,2-difluoro-2-(7-methoxy-2-oxo-2H-chromen-3-yl)acetate, C14H12F2O5
  14. The crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)] bis[1′-(diphenylphosphino-κP)-1-cyanoferrocene]disilver(I), C56H56Ag2Fe2N4P2S4
  15. Crystal structure of bis(di-n-butylammonium) tetrachloridodiphenylstannate(IV), C28H50Cl4N2Sn
  16. The crystal structure of poly[(μ5-2-((5-bromo-3-formyl-2-hydroxybenzylidene)amino)benzenesulfonato-κ6O:O:O,O′:O′:O′′)sodium(I)], C13H9O4NSBrNa
  17. Crystal structure of catena-{poly[bis(O,O′-diethyldithiophosphato-S)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)-zinc(II)] di-acetonitrile solvate}, {C20H30N4O4P2S4Zn ⋅ 2 C2H3N}n
  18. Halogen and hydrogen bonding in the layered crystal structure of 2-iodoanilinium triiodide, C6H7I4N
  19. Crystal structure of cyclohexane-1,4-diammonium 2-[(2-carboxylatophenyl)disulfanyl]benzoate — dimethylformamide — monohydrate (1/1/1), [C6H16N2][C14H8O4S2] ⋅ C3H7NO⋅H2O
  20. The synthesis and crystal structure of isobutyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C16H13Cl2F6N3O3S
  21. Isolation and crystal structure of bufotalinin — methanol (1/1), C25H34O7
  22. Crystal structure of benzylbis(1,3-diphenylpropane-1,3-dionato-κ2O,O′) chloridotin(IV), C37H29ClO4Sn
  23. Crystal structure of Bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-methyl-imidazol)}diiodidocadmium(II), [Cd(C11H11N5)2I2], C22H22N10I2Cd
  24. Crystal structure of 4-isobutoxybenzaldehyde oxime, C11H15NO2
  25. The crystal structure of bis(acetato-κ1O)-bis(N′-hydroxypyrimidine-2-carboximidamide-κ2N,N′)manganese(II) — methanol (1/2), C14H18MnN8O6, 2(CH3OH)′
  26. Crystal structure of poly[bis(μ2-bis(4-(1H-imidazol-1-yl)phenyl)amine-κ2N:N′)-bis(nitrato-κO)cadmium(II)], C36H30CdN12O6
  27. Crystal structure and optical properties of 1,6-bis(methylthio)pyrene, C18H14S2
  28. The crystal structure of hexaquamagnesium(II) bis(3,4-dinitropyrazol-1-ide), C6H14MgN8O14
  29. Halogen bonds in the crystal structure of 4,3:5,4-terpyridine – 1,4-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  30. Crystal structure and photochromic properties of a novel photochromic perfluordiarylethene containing a triazole bridged pyridine group moiety, C24H18F6N4S2
  31. Crystal structure of bis[(μ3-oxido)-(μ2-(N,N-diisopropylthiocarbamoylthio) acetato-κ2O,O′)-((N,N-diisopropylthiocarbamoylthio)acetato-κO)-bis(di-4-methylbenzyl-tin(IV))], C100H136N4O10S8Sn4
  32. Crystal structure of dibromidobis(4-bromobenzyl)tin(IV), C14H12Br4Sn
  33. The crystal structure of (4Z)-2-[(E)-(1-ethyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-ylidene)methyl]-4-[(1-ethyl-3,3-dimethyl-3H-indolium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate, C30H32N2O2
  34. The crystal structure of (E)-3-(4-(dimethylamino)styryl)-5,5-dimethylcyclohex-2-en-1-one, C18H23NO
  35. Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4
  36. Crystal structure of poly[μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4-sulfidobenzoate-κ2O:S)cobalt(II)] dihydrate, C42H44Co2N8O7S2
  37. Crystal structure of 8-(3,4-dimethylbenzylidene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C17H18O4
  38. Crystal structure of 4-(2-bromo-4-(6-morpholino-3-phenyl-3H-benzo[f]chromen-3-yl) cyclohexa-2,5-dien-1-yl)morpholine, C33H31BrN2O
  39. Synthesis and crystal structure of 2-((1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)methylene)-2,3-dihydro-1H-inden-1-one, C23H16N2OS
  40. Crystal structure of poly[(μ2-1,1′-(oxybis(4,1-phenylene)bis(1H-imidazole)-κ2N,N′)(μ2-1,3-benzenecarboxylato-κ3O,O′:O′′)zinc(II)] dihydrate, C26H22N4O7Zn
  41. Crystal structure of diaqua-bis(cinnamato-κ2O,O′)zinc(II), C18H18ZnO6
  42. Crystal structure of 2-(prop-2-yn-1-yloxy)-1-naphthaldehyde, C14H10O2
  43. Crystal structure and photochromic properties of 1-(2-methyl-5-phenyl-3-thienyl)-2-{2-methyl-5-[4-(9-fluorenone hydrazone)-phenyl]-3-thienyl}perfluorocyclopentene, C41H26F6N2S2
  44. Hydrothermal synthesis and crystal structure of cylo[tetraaqua-bis(μ2-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′)-bis(μ2-4-nitro-phthalate-κ2O,O′)dinickel(II)], C26H23N5O8Ni
  45. Crystal structure of 3-[methyl(phenyl)amino]-1-phenylthiourea, C14H15N3S
  46. Crystal structure of 1-(4-chlorophenyl)-3-[methyl(phenyl)amino]thiourea, C14H14ClN3S
  47. Crystal structure of 2-tert-butyl-1H-imidazo[4,5-b]pyridine, C10H13N3
  48. Crystal structure of 5-carboxy-2-(2-carboxyphenyl)-1H-imidazol-3-ium-4-carboxylate dihydrate, C12H8N2O6⋅2(H2O)
  49. The crystal structure of dichlorido-μ2-dichlorido-(η2-1,4-bis(4-vinylbenzyl)-1,4-diazabicyclo[2.2.2]octane-1,4-diium)dicopper(I), C24H30N2Cu2Cl4
  50. Crystal structure of 4-bromobenzyl (Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C22H29BrN2OS
  51. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2
  52. Crystal structure of 3,5-bis(trifluoromethyl)benzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C30H33F6N3S
  53. The crystal structure of 3-methoxyphenanthridin-6(5H)-one, C14H11NO2
  54. Crystal structure of 4-(5,5-difluoro-1,3,7,9-tetramethyl-3H,5H-5λ4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-10-yl)pyridin-1-ium tetraiodidoferrate(III), C18H19BF2FeI4N3
  55. Crystal structure of 2-(3-methoxyphenyl)-3-((phenylsulfonyl)methyl)imidazo[1,2-a]pyridine, C21H18N2O3S
  56. Crystal structure of [(2-(2-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) perchlorate, C29H50Cl2N4NiO8
  57. Crystal structure of (Z)-6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-(quinoxalin-2-ylmethylene)hydrazinyl)-2,3-dihydroinden-1-one, C35H35N7O
  58. 5-Methyl-N′-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide, C22H22N8O2
  59. Crystal structure of 2,3-dichloro-6-methoxyquinoxaline, C9H6Cl2N2O
  60. Synthesis and crystal structure of 7-chloro-2-(ethylsulfinyl)-6-fluoro-3-(1H-pyrazole-1-yl)-4H-thiochromen-4-one, C13H10FN3OS2
  61. Crystal structure of 4-ethylpiperazine-1-carbothioic dithioperoxyanhydride, C14H26N4S4
  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
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