Home Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
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Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5

  • You-Yuan Guo , Huan Wang , Xin Ma and Ying Fu ORCID logo EMAIL logo
Published/Copyright: November 9, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 2

Abstract

C19H19Cl2NO5, orthorhombic, Pbca (no. 61), a = 12.6750(18) Å, b = 11.0927(17) Å, c = 28.400(4) Å, V = 3993.0(10) Å3, Z = 8, Rgt(F) = 0.0700, wRref(F2) = 0.2011, T = 293(2) K.

CCDC no.: 1959881

The crystal structure is shown in the figure (Hydrogen atoms are omitted for clarity). 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:Block, colorless
Size:0.15 × 0.12 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.35 mm−1
Diffractometer, scan mode:Bruker D8 VENTURE PHOTON II, φ and ω-scans
θmax, completeness:28.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:35421, 4974, 0.067
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2812
N(param)refined:246
Programs:Bruker programs [1], SHELX [2], DIAMOND [3]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.80420(11)1.21969(12)0.06655(5)0.1024(5)
Cl20.62195(10)1.07126(13)0.04608(4)0.0920(4)
N10.67630(19)0.9859(3)0.15407(9)0.0524(7)
O10.8318(2)0.9969(3)0.11574(11)0.0948(11)
O20.52355(16)0.8104(2)0.17957(9)0.0680(7)
O30.6905(2)0.5503(3)0.30061(10)0.0808(9)
O40.86288(17)0.5906(2)0.29452(8)0.0621(7)
O50.9617(4)0.2522(3)0.38214(15)0.1489(19)
C10.7004(3)1.1364(4)0.09129(13)0.0689(10)
H10.65661.18950.11080.083*
C20.7438(3)1.0328(3)0.12162(12)0.0622(9)
C30.5632(3)1.0163(3)0.15892(13)0.0626(9)
H3A0.54501.08120.13750.075*
H3B0.54861.04290.19080.075*
C40.4995(3)0.9079(3)0.14788(13)0.0632(9)
H4A0.42520.92760.15020.076*
H4B0.51370.88270.11580.076*
C50.6247(2)0.8044(3)0.19542(11)0.0488(7)
C60.7045(2)0.8858(3)0.18279(10)0.0466(7)
C70.8047(2)0.8701(3)0.20146(12)0.0552(8)
H70.85860.92260.19280.066*
C80.8253(2)0.7782(3)0.23246(11)0.0529(8)
H80.89290.76880.24470.063*
C90.7457(2)0.6995(3)0.24560(10)0.0482(7)
C100.6457(2)0.7122(3)0.22676(11)0.0526(8)
H100.59250.65870.23520.063*
C110.7598(3)0.6060(3)0.28245(11)0.0550(8)
C120.8802(2)0.5307(3)0.33723(11)0.0509(8)
C130.9125(3)0.4178(4)0.33704(13)0.0691(10)
H130.91980.37690.30870.083*
C140.9366(4)0.3570(4)0.38123(16)0.0835(13)
C150.9331(3)0.4297(4)0.42524(13)0.0702(10)
H15A1.00180.46590.43030.084*
H15B0.91900.37640.45160.084*
C160.8505(3)0.5285(3)0.42455(12)0.0580(8)
C170.8672(3)0.6037(3)0.38008(12)0.0650(9)
H17A0.80720.65700.37600.078*
H17B0.92940.65350.38420.078*
C180.8626(5)0.6085(5)0.46788(16)0.1056(17)
H18A0.93210.64280.46830.158*
H18B0.85210.56110.49580.158*
H18C0.81110.67190.46680.158*
C190.7407(3)0.4741(5)0.42446(15)0.0827(13)
H19A0.68920.53740.42280.124*
H19B0.73030.42860.45280.124*
H19C0.73310.42190.39770.124*

Source of material

Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate was synthesized with methyl 4-amino-3-hydroxybenzoate (18 mmol) and 1,2-dibromoethane (22 mmol) as raw materials, anhydrous K2CO3 (90 mmol) as the attaching acid agent in 50 mL DMAC, refluxed for 7 h at 80 °C (monitored by TLC) [4]. After the reaction, K2CO3 was removed by vacuum filtration, and the organic phase was separated with saturated salt water and ethyl acetate. The solution was dried by anhydrous Na2SO4 for 30 min, and then Na2SO4 was removed by vacuum filtration. The solvent was removed under vacuum. The crude product, red-brown solid was purified on silica gel by column chromatography [V(ethyl acetate):V(petroleum ether)=1:3] until a brown solid, methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate, was obtained in 30% yield [5]. Methyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate (2.02 mmol) and 5% NaOH aq. (15 mL) were added to 25 mL EtOH to reflux for 5 h at 65 °C. After the reaction, the solution was diluted with water, cooled to room temperature, adjusted to pH = 5–6 with concentrated hydrochloric acid, extracted with CHCl3, and the organic layer was dried over anhydrous Na2SO4 for 30 min. Na2SO4 was removed by vacuum filtration, and then the solvent was removed under vacuum evaporating to obtain a light brown powder, 3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid in 90% yield [6]. The acid (6.7 mmol) was dissolved in 25 mL THF, and 2,2-dichloroacetyl chloride (8.0 mmol) was added, whereas the reaction mixture was cooled by an ice-water bath. The mixture was reacted at room temperature for 2 h. After the reaction, the solvent was removed under vacuum. The crude product was washed with 30 mL CH2Cl2, and then the solvent was removed by filtration, Repeating three times to remove unreacted acid chloride. Light brown solid, 4-(2,2-dichloroacetyl)-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid was obtained in 96% yield. The acid (16.2 mmol) and SOCl2 (48.6 mmol) were dissolved in 25 mL THF, and DMF (5 drops) were used as catalyst. The mixture was refluxed for 2 h at 65 °C. After the reaction, the solvent was removed under vacuum evaporating to obtain 4-(2,2-dichloroacetyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbonyl chloride. The acid chloride (10.6 mmol) was reacted with 5,5-dimethylcyclohexane-1,3-dione (12.7 mmol), Et3N (31.8 mmol) as the attaching acid agent in 25 mL THF (monitored by TLC). After the reaction an orange solid of the title compound was obtained in 81% yield.

Experimental details

The C—H atoms were then constrained to an ideal geometry, with C—H distances of 0.93–0.96 Å. The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(Cmethyl) and the Uiso values of all other hydrogen atons were set to 1.2Ueq(C).

Discussion

Cyclohexanedione derivatives were critically important used as synthons and biological activities materials [7]. They were also used as medical or pharmaceutical intermediates [8], which have received great interest because of their excellent pharmacological activity and biological activity, organic synthesis intermediates, and agricultural chemicals [9], [10], [11]. 4-Hydroxyphenylpyruvate dioxygenase (HPPD), a target for green herbicide discovery, has attracted a large number of attention owing to controlling efficacy of resistant weeds [12], [13]. It is an important enzyme in the tyrosine metabolic pathway, belonging to the large family of 2-his-1-carboxylate facial triad oxidative enzymes. As an important enzyme correlated to the pigment synthesis and tyrosine catabolism in most organisms, HPPD is important in agricultural areas [14]. A large number of HPPD inhibitors have been discovered, researched and applied to control weed in the field of agrochemicals in recent several decades [15]. Based on our previous efforts to find novel HPPD-inhibiting compounds [16], herein we reported the synthesis and the crystal structure of substituted benzoxazine-cyclohexanedione.

In the crystal structure, the distance of C12–C13 (1.318(5) Å) is closer to the typical C=C bond, and the C13—C14 bond (1.457(6) Å) is shorter than typical C—C bond which is made by conjugation of carbonyl and C=C bond (C12—C13). The N atom and O atom form a conjugated system with benzene ring while methylene group does not. The carbonyl (C2=O1) forms a conjugated system with the oxazine ring. The mean plane of the cyclohexanedione is almost perpendicular to the mean plane of the benzoxazine moiety (see the figure). The van der Waals forces connect molecules into a one-dimensional chain structure.

Funding source: Northeast Agricultural University

Award Identifier / Grant number: 201910224019

Funding statement: The authors gratefully acknowledge the support by Undergraduated SIPT program of Northeast Agricultural University (No. 201910224019). We thank the editor for providing the figure.

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Received: 2019-09-10
Accepted: 2019-10-17
Published Online: 2019-11-09
Published in Print: 2020-02-25

©2019 You-Yuan Guo 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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  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
https://doi.org/10.1515/ncrs-2019-0671
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Articles in the same Issue

  1. Frontmatter
  2. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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