Home Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
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Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3

  • Fanchao Meng , Litong Wang , Quanxiang Han ORCID logo EMAIL logo , Jinfang Wang EMAIL logo and Xiaoxin Zheng ORCID logo
Published/Copyright: December 9, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 1

Abstract

C14H14ClN3, monoclinic, P21/n (no. 14), a = 16.8486(5) Å, b = 8.1171(2) Å, c = 19.9901(7) Å, β = 113.906(4)°, V = 1499.35(15) Å3, Z = 8, R gt(F) = 0.0466, wRref (F 2) = 0.1206, T = 293(2) K.

CCDC no.: 2388511

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 needle
Size: 0.30 × 0.08 × 0.06 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 2.57 mm−1
Diffractometer, scan mode: ROD, Synergy Custom system, HyPix, ω
θ max, completeness: 76.4°, >99 %
N(hkl)measured, N(hkl)unique, R int: 16054, 4902, 0.058
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3,763
N(param)refined: 329
Programs: CrysAlisPRO 1 , SHELX 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
Cl1 −0.14650 (3) −0.38335 (7) 0.09986 (3) 0.02883 (16)
Cl2 0.66924 (3) −0.37758 (7) 0.19357 (3) 0.02821 (16)
N1 −0.01553 (12) −0.3182 (2) 0.06612 (10) 0.0234 (4)
N2 −0.10512 (11) −0.0164 (2) 0.15555 (10) 0.0246 (4)
N3 −0.00462 (11) 0.1541 (2) 0.14665 (10) 0.0219 (4)
N4 0.52559 (12) −0.3242 (2) 0.07883 (10) 0.0228 (4)
N5 0.62693 (12) −0.0099 (2) 0.22228 (10) 0.0245 (4)
N6 0.51923 (11) 0.1529 (2) 0.14788 (10) 0.0209 (4)
C1 −0.06511 (14) −0.2569 (3) 0.09540 (12) 0.0233 (5)
C2 0.04954 (14) −0.2188 (3) 0.06234 (12) 0.0218 (5)
C3 0.10246 (14) −0.2891 (3) 0.03026 (12) 0.0248 (5)
H3 0.093260 −0.397664 0.014036 0.030*
C4 0.16728 (14) −0.1990 (3) 0.02279 (12) 0.0261 (5)
H4 0.202093 −0.246819 0.001989 0.031*
C5 0.18096 (14) −0.0353 (3) 0.04646 (12) 0.0259 (5)
H5 0.224265 0.025676 0.040333 0.031*
C6 0.13156 (14) 0.0368 (3) 0.07858 (12) 0.0235 (5)
H6 0.142479 0.145176 0.094817 0.028*
C7 0.06428 (13) −0.0520 (3) 0.08724 (11) 0.0203 (5)
C8 0.00618 (14) 0.0056 (3) 0.11783 (11) 0.0207 (5)
C9 −0.05732 (13) −0.0967 (3) 0.12333 (11) 0.0208 (5)
C10 −0.07158 (14) 0.1315 (3) 0.16792 (13) 0.0259 (5)
H10 −0.091492 0.214390 0.189350 0.031*
C11 0.04226 (14) 0.3083 (3) 0.15281 (12) 0.0238 (5)
H11A 0.005865 0.398897 0.155035 0.029*
H11B 0.053352 0.322864 0.109199 0.029*
C12 0.12865 (14) 0.3157 (3) 0.22008 (12) 0.0244 (5)
H12 0.161357 0.214631 0.222020 0.029*
C13 0.18085 (16) 0.4625 (3) 0.21278 (14) 0.0302 (5)
H13A 0.193133 0.448630 0.170232 0.045*
H13B 0.234371 0.469711 0.255501 0.045*
H13C 0.147969 0.561684 0.208018 0.045*
C14 0.11328 (17) 0.3282 (3) 0.28990 (13) 0.0309 (5)
H14A 0.167993 0.325179 0.331555 0.046*
H14B 0.078011 0.237410 0.292301 0.046*
H14C 0.084163 0.429863 0.289856 0.046*
C15 0.58071 (14) −0.2579 (3) 0.13897 (12) 0.0226 (5)
C16 0.45605 (13) −0.2288 (3) 0.03313 (12) 0.0207 (5)
C17 0.39750 (14) −0.3055 (3) −0.03137 (12) 0.0242 (5)
H17 0.405515 −0.415428 −0.040204 0.029*
C18 0.32908 (14) −0.2197 (3) −0.08100 (13) 0.0257 (5)
H18 0.290825 −0.271449 −0.123284 0.031*
C19 0.31647 (14) −0.0531 (3) −0.06818 (12) 0.0254 (5)
H19 0.270177 0.004939 −0.102338 0.030*
C20 0.37197 (14) 0.0242 (3) −0.00568 (12) 0.0225 (5)
H20 0.362917 0.134296 0.002083 0.027*
C21 0.44280 (14) −0.0615 (3) 0.04710 (12) 0.0202 (4)
C22 0.50633 (13) 0.0010 (3) 0.11425 (12) 0.0202 (4)
C23 0.57393 (14) −0.0964 (3) 0.16080 (12) 0.0215 (5)
C24 0.59225 (14) 0.1371 (3) 0.21183 (13) 0.0242 (5)
H24 0.614963 0.223314 0.244737 0.029*
C25 0.46902 (14) 0.3037 (3) 0.12117 (13) 0.0237 (5)
H25A 0.456989 0.317587 0.069762 0.028*
H25B 0.503536 0.397108 0.147459 0.028*
C26 0.38325 (14) 0.3031 (3) 0.13036 (12) 0.0226 (5)
H26 0.354904 0.196538 0.113403 0.027*
C27 0.32424 (16) 0.4376 (3) 0.08266 (13) 0.0296 (5)
H27A 0.269962 0.436186 0.087713 0.044*
H27B 0.314022 0.418422 0.032438 0.044*
H27C 0.351554 0.542961 0.097759 0.044*
C28 0.39867 (15) 0.3239 (3) 0.21037 (12) 0.0273 (5)
H28A 0.439008 0.241822 0.239280 0.041*
H28B 0.344710 0.311508 0.215432 0.041*
H28C 0.422032 0.431549 0.226860 0.041*

1 Source of materials

The initial step involved the nitration of 2,4-dihydroxyquinoline using concentrated nitric acid (HNO3) at 70 °C, resulting in the formation of mononitrated 2,4-dihydroxyquinoline (Compound 1) with a yield of 85 %. Without subsequent purification, Compound 1 underwent chlorination with phosphorus oxychloride (POCl3), yielding a dichloro derivative. This intermediate was then reacted with isobutyl amine in the presence of potassium carbonate (K2CO3) in ethanol, affording 2-chloro-N-isobutyl-3-nitroquinolin-4-amine (Compound 2) in a yield of 40 % over the two steps. Following this, a Bechamp reduction utilizing an iron powder/NH4Cl system successfully produced 2-chloro-N4-isobutylquinoline-3,4-diamine in a yield of 87 %. Finally, treatment with triethyl orthoformate (CH(OEt)3) at 60 °C in a yield of 65 %.

2 Experimental details

All hydrogen atoms were placed in idealized positions. Their U iso values were set to 1.2U eq of the parent atoms.

3 Comment

The 1H-imidazo[4,5-c]quinolines represent an important class of N-tricyclic compounds, commonly known as imidazoquinolines. These derivatives have attracted considerable attention due to their diverse biological activities, including antimalarial, anticonvulsant, and cardiovascular effects. 4 , 5 , 6 For example, imiquimod (Aldara) serves as an immune response modifier primarily used in the treatment of anogenital warts. 7 And, 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline acts as an intermediate in the synthesis of various imidazoquinoline derivatives.

The crystal structure of 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline is shown in the above figure. The bond lengths of C1–Cl1, C1=N1, C9=N2, and C10=N3 in the title molecule are 1.744, 1.298, 1.382 and 1.370 Å, respectively, which are similar with its analogs. 8 , 9 The thirteen atoms of C1–C10, N1–N3 are in the same plane. Besides, the distance between two adjacent molecules in parallel arrangement is 3.339 Å, indicating π–π stacking interaction between the aromatic cycles.

Corresponding authors: Quanxiang Han, College of Biological and Chemical Engineering, Qilu Institute of Technology, Jinan, 250100, P.R. China, E-mail: ; and Jinfang Wang, Department of Basic Courses, China Fire and Rescue Institute, Beijing, 102202, P.R. China, E-mail:

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

  2. Research funding: the project ZR2024QE449 supported by Shandong Provincial Natural Science Foundation and the Research Program QIT23TP002 of Qilu Institute of Technology.

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

References

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Received: 2024-10-03
Accepted: 2024-11-26
Published Online: 2024-12-09
Published in Print: 2025-02-25

© 2024 the author(s), 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 the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
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  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
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  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
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https://doi.org/10.1515/ncrs-2024-0389
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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