Home Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
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Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2

  • Marole M. Maluleka ORCID logo EMAIL logo and Malose J. Mphahlele ORCID logo
Published/Copyright: April 5, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 3

Abstract

C15H10BrClO2 monoclinic P21/c (no. 14), a = 9.2173(6) Å, b = 20.7174(14) Å, c = 6.9035(4) Å, β = 99.332(3)°, V = 1300.83(14) Å3, Z = 4, Rgt(F) = 0.0153, wRref(F2) = 0.121, T = 173(2) K.

CCDC no.: 2154587

The crystal 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: Colorless plate
Size 0.277 × 0.58 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.5 mm−1
Diffractometer, scan mode: Bruker SMART, φ and ω-scans
θmax, completeness: 25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 45410, 2418, 0.044
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2272
N(param)refined: 172
Programs: Bruker programs [1], WinGX and ORTEP [2], SHELX [3]
Table 2:

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

x y z Uiso*/Ueq
C1 0.8044 (4) 0.65976 (19) 0.2707 (5) 0.0227 (8)
C2 0.9437 (4) 0.6376 (2) 0.2510 (6) 0.0260 (8)
H2 0.960269 0.592811 0.234161 0.031*
C3 1.0585 (4) 0.6814 (2) 0.2563 (6) 0.0256 (8)
H3 1.154422 0.666571 0.245674 0.031*
C4 1.0322 (4) 0.74714 (19) 0.2772 (6) 0.0234 (8)
C5 0.8955 (4) 0.76990 (19) 0.2954 (5) 0.0236 (8)
H5 0.879634 0.814846 0.309576 0.028*
C6 0.7791 (4) 0.72597 (19) 0.2930 (5) 0.0221 (8)
C7 0.6304 (4) 0.75000 (19) 0.3059 (6) 0.0251 (8)
C8 0.5147 (5) 0.69829 (19) 0.2947 (7) 0.0295 (9)
H8A 0.466095 0.693426 0.156734 0.035*
H8B 0.439063 0.711713 0.373311 0.035*
C9 0.5786 (4) 0.6334 (2) 0.3701 (6) 0.0281 (9)
H9 0.617842 0.637057 0.513457 0.034*
C10 0.4593 (5) 0.5829 (2) 0.3394 (7) 0.0300 (9)
C11 0.4142 (5) 0.5541 (2) 0.1583 (8) 0.0411 (11)
H11 0.464881 0.563258 0.05218 0.049*
C12 0.2939 (6) 0.5113 (2) 0.1305 (8) 0.0414 (11)
H12 0.262506 0.491296 0.006984 0.05*
C13 0.2231 (5) 0.4994 (2) 0.2885 (7) 0.0331 (10)
C14 0.2665 (5) 0.5277 (2) 0.4690 (7) 0.0358 (10)
H14 0.215414 0.518839 0.574981 0.043*
C15 0.3862 (5) 0.5694 (2) 0.4938 (7) 0.0331 (9)
H15 0.417857 0.58885 0.618176 0.04*
O1 0.6016 (3) 0.80720 (13) 0.3188 (5) 0.0326 (7)
O2 0.6962 (3) 0.61472 (14) 0.2667 (4) 0.0269 (6)
Cl1 0.07143 (13) 0.44768 (6) 0.2577 (2) 0.0490 (4)
Br1 1.19037 (4) 0.80650 (2) 0.28426 (6) 0.03088 (17)

Source of material

A stirred mixture of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one (0.50 g, 1.48 mmol) and piperidine (0.15 g, 1.78 mmol) in ethanol (10 mL) was heated at 80 °C for 2 h and then allowed to cool to RT. The mixture was quenched with an ice-cold water and the resulting precipitate was filtered and recrystallized from ethanol to afford 6-bromo-4′-chloroflavanone as a yellow solid. (0.38 g, 92%), mp.158–159 °C (EtOH) (Lit. [4] 157–159 °C). The crystals for X-ray analysis were prepared by slow evaporation from CH2Cl2.

Experimental details

X-ray single crystal data were collected on a Bruker D8 Venture diffractometer with graphite-monochromated Moκα (λ = 0.71073 A) radiation at 173 K using an Oxford Cryostream 600 low-temperature controller. Data reduction was carried out using the program SAINT+, version 6.02 [1] and empirical absorption corrections were made using SADABS [1]. The structure was solved in the WinGX [2] Suite of programs, using intrinsic phasing through SHELXT [3] and refined using full-matrix least-squares/difference Fourier techniques on F2 using SHELXL-2017 [3]. All hydrogen atoms were placed at idealized positions and refined as riding atoms with isotropic parameters 1.2 or 1.5 times those of their parent atoms. The largest difference density peaks must be attributed to a slight disorder of the bromo substituent distributed over several postions.

Comment

Flavanones (2,3-dihydro-2-phenylchromen-4-ones) are compounds widely distributed in the plant families Compositae, Leguminosae, Lamiaceae and Rutaceae [5]. These heterocyclic compounds have attracted significant interest due to their wide range of pharmacological properties including anticancer, antimicrobial, antiproliferative, anti-inflammatory, cardiovascular, antimalarial, antiangiogenic, radical scavenging and hypotensive activities [6]. Their biological properties are closely related to the skeleton and substitution patterns, which continue to motivate research on their synthesis and evaluation of their bioactivity [7]. They are readily accessible via acid- or base-mediated cyclization (intramolecular Michael addition) of the corresponding chalcone (1,3-diphenyl-2- propene-1-one) precursors prepared, in turn, via acid- or base-mediated Claisen–Schmidt condensation reaction between 2-hydroxyacetophenones and benzaldehyde derivatives [6, 7]. The introduction of one or more halogen atoms into A or B-ring of flavonoids affords the corresponding halogenated derivatives with potential biological activity [8]. Halogen atom/s are very useful to modulate the electronic and steric characteristics of drugs and may also influence the hydrophilic-hydrophobic balance of the molecules [9]. Although the flavanone nucleus does not exert any anxiolytic activity [10], substitution at position 6 of the flavanone nucleus with a bromine atom was found to lead to 6-bromoflavanone [11] or 6-bromoflavone derivatives with elevated anxiolytic properties [12]. Halogenated flavanones, on the other hand, are not only of interest from the medicinal chemistry context [9, 11], their conformations and crystalline structures continue to attract attention to explore non-covalent (intramolecular and intermolecular) interactions, control molecular conformations and improve the physicochemical properties (durability, solubility and bioavailability) of the drug molecules. Based on the diverse biological activities of flavanone derivatives and our longstanding interest in their synthesis and chemical transformation, we decided to synthesize 6-bromo-4′-chloroflavanone and study its geometry in the solid state.

This compound crystallizes in the monoclinic space group P21/c containing a single molecule in the asymmetric unit as shown in the Figure. The racemic naturally occurring naringenin (5,7,4′-trihydroxyflavanone/5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one) was also found to crystallize in a monoclinic crystal system in the space group P21/c with one molecule in the asymmetric unit [13]. The solid-state structures of the pure R- and S-enantiomers of naringenin, on the other hand, were previously found to crystallize in the monoclinic space group P21 with two independent molecules having slightly different geometries [13].

The single crystal structure of the title compound shows the two aromatic rings (A and B) are linked by a pyranone ring (C), which adopts a chair-like conformation in which C9 atom deviates from the plane drawn through the remaining five atoms of this heterocycle with a bond angle, O(2)–C(9)–C(8), of 110.3(3)°. The 2-phenyl ring occupies a quasi-equatorial orientation relative to the flattened portion of the heterocyclic ring and the methine hydrogen atom is anti to one of the methylene hydrogen and gauche to the other. A similar orientation of the 2-phenyl group was observed before in the crystal structures of the racemic and pure enantiomers of naringenin [13]. The ipso angle α for substituted benzene derivatives is sensitive to the electron withdrawing inductive effect of the substituent and this observation has previously been rationalized in terms of the hybridization effects of the ipso carbon [14]. The presence of bromine atom on the A ring resulted in alternate positive and negative internal angle distortion effect, and the trend is as follows: ipso angle, C(5)–C(4)–C(3) = 121.5(4)°; ortho angles, C(2)–C(3)–C(4) = 119.8(4)° & C(4)–C(5)–C(6) = 119.2(4)°; meta angles, C(3)–C(2)–C(1) = 119.5(4)° and C(1)–C(6)–C(5) = 119.6(4)° and para angle, C(2)–C(1)–C(6) = 120.4(4)°. The 2-(4-chlorophenyl) group exhibits a similar trend: ipso angle, C(14)–C(13)–C(12) = 122.3(4)°, ortho angles, C(13)–C(12)–C(11) = 117.8(5)° & C(13)–C(14)–C(15) = 119.0(4)°; meta angles, C(10)–C(11)–C(12) = 120.6(4)°, C(10)–C(15)–C(14) = 120.5(4)°; and para angle, C(15)–C(10)–C(11) = 119.8(4)°.

This contribution, which forms part of our longstanding interest on the geometry and conformation of halogenated oxygen-based heterocycles represents in our view a valuable contribution to the dataset of flavanones of medicinal potential. Since aryl halides represent important intermediates in metal-catalyzed cross-coupling reactions, nucleophilic aromatic substitution reactions and for the generation of free-radical intermediates [15], the reported compound represents a suitable scaffold for further chemical transformation to generate polycarbo-substituted derivatives.

Corresponding author: Marole M. Maluleka, Department of Chemistry, Faculty of Science and Agriculture School of Physical and Mineral Science, University of Limpopo, Private Bag X1106 Polokwane, Sovenga 0727, South Africa, E-mail:

Funding source: University of Limpopo

Funding source: University of South Africa

Funding source: National Research Foundation (NRF, SA) in South Africa

Award Identifier / Grant number: UID: 138285

Acknowledgements

The University of the Witwatersrand for X-ray diffraction data using the single-crystal diffractometer purchased through the NRF Equipment Programme (UID: 78572).

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This project was funded by the University of Limpopo, University of South Africa and the National Research Foundation (NRF, SA) in South Africa (UID: 138285).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-03-06
Accepted: 2022-03-29
Published Online: 2022-04-05
Published in Print: 2022-06-27

© 2022 Marole M. Maluleka and Malose J. Mphahlele, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
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https://doi.org/10.1515/ncrs-2022-0104
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
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