Home Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
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Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3

  • Jacques Joubert ORCID logo EMAIL logo and Germaine B. Foka
Published/Copyright: December 5, 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

C22H23BrN2O3, monoclinic, P21/c (no. 14), a = 5.9023(9) Å, b = 14.554(2) Å, c = 22.801(4) Å, β = 90.801(2)°, V = 1958.5(5) Å3, Z = 4, Rgt(F) = 0.0388, wRref(F2) = 0.0961, T = 100(2) K.

CCDC no.: 1964544

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 rod
Size:0.23 × 0.11 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.13 mm−1
Diffractometer, scan mode:Bruker APEX II DUO, φ and ω
θmax, completeness:28.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:38722, 4874, 0.036
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4045
N(param)refined:253
Programs:Bruker [1], SHELX [3], X-Seed [3], [4], WinGX/ORTEP [5]
Table 2:

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

AtomxyzUiso*/Ueq
Br10.76860(5)0.24905(2)0.84133(2)0.03223(9)
C20.1101(4)0.50631(16)0.09850(10)0.0244(5)
C3−0.1121(4)0.54291(16)0.08404(10)0.0242(5)
H3−0.1527200.5528870.0440850.029*
C4−0.2619(4)0.56302(15)0.12596(10)0.0229(4)
H4−0.4060810.5872220.1152090.027*
C5−0.3533(4)0.56749(15)0.23337(10)0.0229(4)
H5−0.4978340.5935860.2252250.028*
C6−0.2908(4)0.54903(15)0.29057(10)0.0227(4)
H6−0.3914380.5626930.3215280.027*
C7−0.0781(4)0.50998(15)0.30307(10)0.0213(4)
C80.0720(4)0.49083(15)0.25835(10)0.0213(4)
H80.2166690.4648760.2665930.026*
C90.0038(4)0.51089(15)0.20086(9)0.0202(4)
C10−0.2070(4)0.54841(15)0.18681(10)0.0207(4)
C110.1638(4)0.44180(15)0.37703(10)0.0222(4)
H11A0.3035930.4761930.3678590.027*
H11B0.1661050.3822230.3560980.027*
C120.1435(4)0.42735(15)0.44266(9)0.0221(4)
H12A0.1347360.4879110.4622560.027*
H12B0.0012430.3938330.4505830.027*
C130.3590(4)0.39435(15)0.53062(9)0.0221(4)
H13A0.2195390.3754730.5510060.027*
H13B0.3812500.4610350.5370560.027*
C140.5601(4)0.34196(15)0.55555(10)0.0228(4)
H14A0.6996770.3612950.5353810.027*
H14B0.5786470.3561860.5978030.027*
C150.5018(4)0.22343(16)0.48540(10)0.0260(5)
H15A0.4766910.1567320.4798090.031*
H15B0.6428650.2404150.4650730.031*
C160.3038(4)0.27639(15)0.45873(10)0.0236(5)
H16A0.2921900.2629810.4162340.028*
H16B0.1612500.2563860.4771940.028*
C170.7166(4)0.19038(17)0.57274(10)0.0280(5)
H17A0.8593390.2105580.5544420.034*
H17B0.6946440.1244460.5636190.034*
C180.7354(4)0.20272(15)0.63836(10)0.0222(4)
C190.5547(4)0.17739(16)0.67359(11)0.0269(5)
H190.4233460.1505670.6561510.032*
C200.5642(4)0.19086(16)0.73373(11)0.0264(5)
H200.4400230.1738610.7574840.032*
C210.7569(4)0.22940(15)0.75877(10)0.0223(4)
C220.9400(4)0.25468(16)0.72513(11)0.0260(5)
H221.0713140.2809820.7428650.031*
C230.9277(4)0.24079(16)0.66470(11)0.0265(5)
H231.0525760.2575520.6411240.032*
N10.3342(3)0.37579(12)0.46753(8)0.0205(4)
N20.5268(3)0.24332(12)0.54787(8)0.0230(4)
O10.1582(3)0.49123(11)0.15792(7)0.0226(3)
O20.2580(3)0.48714(13)0.06486(7)0.0318(4)
O3−0.0341(3)0.49394(11)0.36086(7)0.0246(3)

Source of materials

7-Hydroxycoumarin (1.0 eq.) and K2CO3 (1.1 eq.) were suspended in 10 mL of acetone. 1,2-Dibromoethane (1.1 eq.) was slowly added and the mixture was reacted under reflux for 4 h. The resulting solution was dried in vacuo. Dichloromethane was added and the precipitate that formed was filtered out rendering 7-(2-bromoethoxy)-2H-chromen-2-one as a white solid that was used in the next step. Yield 59%; 1H-NMR (400 MHz, CDCl3) δ/p.p.m. = 7.65–7.61 (d, J = 9.4 Hz, 1H), 7.40–7.37 (d, J = 8.8, 1H), 6.87–6.84 (d, J = 8.4 Hz, 1H), 6.80 (s, 1H), 6.82–6.24 (d, J = 9.6 Hz, 1H), 4.36–4.32 (t, 2H), 3.68–3.64 (t, 2H). A solution of 7-(2-bromoethoxy)-2H-chromen-2-one (1.0 eq.) and 1-(4-bromobenzyl)-piperazine (1.0 eq) in acetonitrile (10 mL) was refluxed in the presence of anhydrous K2CO3 (1.1 mmol) for 8 h. The reaction mixture was dried in vacuo. The residue was purified by silica gel chromatography using CHCl3/MeOH (50:1) as eluent to obtain the title compound as a light yellow viscous oil. Recrystallisation from ethanol rendered colourless rod crystals. Yield 32%; 1H-NMR (400 MHz, CDCl3) δ/p.p.m. = 7.63–7.60 (d, J = 9.6 Hz, 1H), 7.43–7.40 (d, J = 8.4 Hz, 2H), 7.36–7.33 (d, J = 8.6 Hz, 1H), 7.20–7.17 (d, J = 8.4 Hz, 2H), 6.84–6.81 (dd, J = 8.4, 2.4 Hz, 1H), 6.80–6.79 (m, 1H), 6.25–6.22 (d, J = 9.6 Hz, 1H), 4.16–4.12 (t, 2H), 3.44 (s, 2H), 2.85–2.81 (t, 2H, Hz), 2.61–2.48 (m, 8H); 13C-NMR (100 MHz, CDCl3) δ = 161.9, 161.2, 155.8, 143.3, 137.1, 131.3, 130.8, 128.7, 120.9, 113.2, 113.0, 112.6, 101.5, 66.5, 62.2, 56.8, 53.6, 52.9.

Experimental details

Data collection and reduction were carried out using the software package APEX3 [1]. The structure was solved and refined using SHELX-2016 [2] employed within X-Seed [3], [4]. Hydrogen atoms were placed in calculated positions using riding models. ORTEP-3 [5] was used to generate the publication material.

Comment

The title compound was studied as part of an ongoing project into the development of coumarin-donepezil hybrid derivatives for the treatment of neurodegenerative disorders and/or tuberculosis [6], [7], [8]. Continued development of these coumarin-donepezil hybrids is motivated by their good biological activities exhibited, e.g. as cholinesterase inhibitors [6], [7], mono-amine oxidase inhibitors [6], [7], neuroprotectants and anti-tubercular abilities [8].

In the crystal structure the coumarin ring system is planar, as confirmed by the dihedral angles of 180.0(2)° and 178.8(2)° for C5—C10—C4—C3 and C8—C9–O1—C2, respectively. As in other coumarin compounds [9], there is asymmetry with respect to the O—C=O and C—C=O bond angles, with values of 116.3(2) and 127.1(2)°. In a similar way, the O1—C9—C8 and C5—C10—C4 angles at the junction of the two fused rings have values of 116.02(19) and 124.6(2)°, respectively. Electron localization is indicated by the C3—C4 bond with a length of 1.343(3) Å. The ether group at C7—O3—C11 is almost co-planar with the coumarin as shown by the dihedral angles of 179.5(2)° and 179.9(2)° for C5—C6—C7—O3 and C9—C8—C7—O3, respectively. The piperazine moiety that links the ethoxy-coumarin derivative with the 4-bromophenyl(methyl) moiety adopts a chair conformation. The parameters for the 4-bromophenyl(methyl) moiety are consistent with structures in the literature [10]. Two important dihedral angles at the tertiary amine groups of the piperazine structure t1 [N1—C12—C11—O3, −179.25(17)°] and t2 [N2—C17—C18—C19, 60.0(3)°] describe the conformation of the molecule.

References

1. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2018).Search in Google Scholar

2. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar

3. Barbour, L. J.: X-Seed − a softwaretool for supramolecular crystallography. J. Supramol. Chem. 1 (2001) 189–191.10.1016/S1472-7862(02)00030-8Search in Google Scholar

4. Atwood, J. L.; Barbour, L. J.: Molecular graphics: from science to art. Cryst. Growth Des. 3 (2003) 3–8.10.1021/cg020063oSearch in Google Scholar

5. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Search in Google Scholar

6. Repsold, B. P.; Malan, S. F.; Joubert, J.; Oliver, D. W.: Multi-targeted directed ligands for Alzheimer’s disease: design of novel lead coumarin conjugates. SAR QSAR Environ. Res. 29 (2018) 231–255.10.1080/1062936X.2018.1423641Search in Google Scholar PubMed

7. Joubert, J.; Foka, G. B.; Repsold, B. P.; Oliver, D. W.; Kapp, E.; Malan, S. F.: Synthesis and evaluation of 7-substituted coumarin derivatives as multimodal monoamine oxidase-B and cholinesterase inhibitors for the treatment of Alzheimer’s disease. Eur. J. Med. Chem. 125 (2017) 853–864.10.1016/j.ejmech.2016.09.041Search in Google Scholar PubMed

8. Kapp, E.; Visser, H.; Sampson, S. L.; Malan, S. F.; Streicher, E. M.; Foka, G. B.; Warner, D. F.; Omoruyi, S. I.; Enogieru, A. B.; Ekpo, O. E.; Zindo, F. T.; Joubert, J.: Versatility of 7-substituted coumarin molecules as antimycobacterial agents, neuronal enzyme inhibitors and neuroprotective agents. Molecules 22 (2017) 1644.10.3390/molecules22101644Search in Google Scholar PubMed PubMed Central

9. Walki, S.; Naveen, S.; Kenchanna, S.; Mahadevan, K. M.; Kumara, M. N.; Lokanath, N. K.: 7-Hydroxy-3-(4-nitrophenyl)-2H-chromen-2-one. IUCrData 1 (2016) x160329.10.1107/S2414314616003291Search in Google Scholar

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Received: 2019-09-30
Accepted: 2019-11-08
Published Online: 2019-12-05
Published in Print: 2020-02-25

©2019 Jacques Joubert 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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  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-2019-0738
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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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