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Crystal structure of (−)-flavesine H, C15H22N2O2

  • Kai Peng , Ding Luo ORCID logo EMAIL logo and Guang-cun Wang EMAIL logo
Published/Copyright: October 30, 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

C15H22N2O2, monoclinic, P21 (no. 4), a = 8.4853(2) Å, b = 19.5759(4) Å, c = 9.0640(2) Å, β = 106.845(2)°, V = 1441.00(6) Å3, Z = 4, R gt (F) = 0.00374, wR ref (F 2) = 0.0991, T = 150 K.

CCDC no.: 2392013

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 × 0.11 × 0.10 mm
Wavelength:

μ:		 Cu Kα radiation (1.54184 Å)

0.73 mm−1
Diffractometer, scan mode:

θ max, completeness:		 SuperNova, ω

74.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 13135, 5610, 0.034
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 5461
N(param)refined: 367
Programs: Olex2, 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
O1 0.0677 (2) 0.64406 (9) 0.4676 (2) 0.0312 (4)
O2 −0.0398 (2) 0.54071 (10) 0.3946 (2) 0.0325 (4)
N1 0.2342 (2) 0.88293 (10) 1.0100 (2) 0.0250 (4)
N2 0.0937 (3) 0.68675 (10) 1.0753 (2) 0.0253 (4)
H2 0.080730 0.642775 1.088276 0.030*
C2 0.2620 (3) 0.93510 (12) 1.1325 (3) 0.0284 (5)
H2A 0.201969 0.977264 1.088893 0.034*
H2B 0.380828 0.946217 1.168477 0.034*
C3 0.2061 (3) 0.91228 (13) 1.2692 (3) 0.0302 (5)
H3A 0.084373 0.913547 1.241358 0.036*
H3B 0.249871 0.944057 1.356499 0.036*
C4 0.2662 (3) 0.84011 (12) 1.3181 (3) 0.0273 (5)
H4A 0.387929 0.839547 1.357058 0.033*
H4B 0.221542 0.824367 1.401708 0.033*
C5 0.2091 (3) 0.79350 (12) 1.1809 (3) 0.0227 (4)
C6 0.2021 (3) 0.81839 (12) 1.0334 (3) 0.0221 (4)
C7 0.1687 (3) 0.76709 (12) 0.9019 (3) 0.0228 (4)
H7 0.272091 0.740381 0.913726 0.027*
C8 0.1234 (3) 0.80092 (13) 0.7436 (3) 0.0312 (5)
H8A 0.124652 0.766616 0.663669 0.037*
H8B 0.011184 0.820487 0.719391 0.037*
C9 0.2471 (4) 0.85701 (14) 0.7445 (3) 0.0357 (6)
H9A 0.359563 0.837566 0.771992 0.043*
H9B 0.223177 0.877524 0.640453 0.043*
C10 0.2374 (4) 0.91131 (13) 0.8601 (3) 0.0349 (6)
H10A 0.333400 0.942130 0.876549 0.042*
H10B 0.136731 0.938913 0.817096 0.042*
C11 0.0367 (3) 0.71732 (12) 0.9208 (3) 0.0238 (5)
H11 −0.064506 0.744516 0.915694 0.029*
C12 −0.0116 (3) 0.66129 (13) 0.7994 (3) 0.0268 (5)
H12A −0.060624 0.683013 0.697835 0.032*
H12B −0.097998 0.632781 0.822312 0.032*
C13 0.1278 (3) 0.61467 (12) 0.7872 (3) 0.0261 (5)
H13A 0.176239 0.591787 0.887508 0.031*
H13B 0.215004 0.642584 0.764062 0.031*
C14 0.0691 (3) 0.56065 (12) 0.6621 (3) 0.0273 (5)
H14A −0.030474 0.538626 0.676404 0.033*
H14B 0.155336 0.525083 0.677879 0.033*
C15 0.0285 (3) 0.58544 (12) 0.4953 (3) 0.0246 (5)
C17 0.1647 (3) 0.72619 (12) 1.1945 (3) 0.0240 (5)
H17 0.186370 0.707345 1.294986 0.029*
O1A 0.2960 (3) 0.33844 (11) 0.1245 (2) 0.0472 (5)
O2A 0.2134 (4) 0.44442 (12) 0.1513 (3) 0.0557 (7)
N1A 0.4754 (3) 0.10655 (10) −0.3462 (3) 0.0285 (4)
N2A 0.2809 (2) 0.29788 (10) −0.4760 (2) 0.0249 (4)
H2AA 0.254774 0.341081 −0.496205 0.030*
C2A 0.5439 (4) 0.06458 (14) −0.4479 (3) 0.0368 (6)
H2AB 0.516018 0.016033 −0.437788 0.044*
H2AC 0.665415 0.068760 −0.414701 0.044*
C3A 0.4784 (4) 0.08591 (14) −0.6156 (3) 0.0370 (6)
H3AA 0.359780 0.074700 −0.654741 0.044*
H3AB 0.537190 0.060645 −0.678211 0.044*
C4A 0.5031 (3) 0.16262 (15) −0.6300 (3) 0.0331 (5)
H4AA 0.622136 0.173228 −0.602999 0.040*
H4AB 0.450926 0.177527 −0.737429 0.040*
C5A 0.4265 (3) 0.19960 (12) −0.5227 (3) 0.0248 (5)
C6A 0.4203 (3) 0.16933 (12) −0.3843 (3) 0.0230 (4)
C7A 0.3672 (3) 0.21316 (12) −0.2689 (3) 0.0234 (5)
H7A 0.464891 0.240971 −0.212318 0.028*
C8A 0.3144 (3) 0.17164 (14) −0.1485 (3) 0.0313 (5)
H8AA 0.303139 0.202139 −0.064982 0.038*
H8AB 0.206226 0.150008 −0.196675 0.038*
C9A 0.4423 (4) 0.11699 (15) −0.0821 (3) 0.0368 (6)
H9AA 0.549619 0.138795 −0.031290 0.044*
H9AB 0.408731 0.090203 −0.003620 0.044*
C10A 0.4600 (4) 0.06985 (14) −0.2091 (3) 0.0366 (6)
H10C 0.558543 0.040806 −0.168267 0.044*
H10D 0.362777 0.039426 −0.240138 0.044*
C11A 0.2329 (3) 0.26319 (12) −0.3523 (3) 0.0231 (4)
H11A 0.130395 0.236452 −0.400269 0.028*
C12A 0.1919 (3) 0.31801 (13) −0.2476 (3) 0.0278 (5)
H12C 0.101107 0.346790 −0.310269 0.033*
H12D 0.152132 0.295109 −0.167830 0.033*
C13A 0.3365 (3) 0.36402 (14) −0.1682 (3) 0.0324 (6)
H13C 0.380657 0.385045 −0.247381 0.039*
H13D 0.424956 0.335786 −0.100272 0.039*
C14A 0.2900 (3) 0.42046 (13) −0.0726 (3) 0.0288 (5)
H14C 0.377674 0.455573 −0.050405 0.035*
H14D 0.187392 0.442392 −0.135672 0.035*
C15A 0.2640 (3) 0.39783 (13) 0.0797 (3) 0.0305 (5)
C17A 0.3626 (3) 0.26502 (12) −0.5568 (3) 0.0247 (5)
H17A 0.379115 0.287390 −0.644186 0.030*
O3 0.0057 (3) 0.55455 (9) 0.1139 (2) 0.0358 (4)
H3D 0.070130 0.521348 0.113187 0.054*
H3C −0.005520 0.554018 0.204122 0.054*
O4 0.1809 (3) 0.42944 (10) 0.4334 (2) 0.0386 (5)
H4C 0.190543 0.433391 0.343010 0.058*
H4D 0.110787 0.459768 0.438147 0.058*

1 Source of material

The dried roots of Sophora flavescens (25.0 kg) were sourced from Xi’an, Shanxi Province, China. After three extractions with 95 % ethanol, the combined extracts were concentrated under vacuum to yield 1.6 kg of residue. This was suspended in water, adjusted to pH 4 with HCl, and partitioned with chloroform. The aqueous phase was then adjusted to pH 9 with ammonium hydroxide and re-extracted with chloroform, yielding 464 g of chloroform-soluble fraction. Chromatography on macroporous resin produced several fractions, with the title compound isolated from the EtOH/H2O (10:90) fraction and crystallized from methanol.

2 Experimental details

Using Olex2, 1 the structure was solved with the ShelXT 2 structure solution program and refined with the ShelXL 3 refinement package.

3 Comment

Matrine-type alkaloids are a class of naturally occurring compounds predominantly found in plants of the Sophora genus. These alkaloids are characterized by their tetracyclic quinolizidine core structure. 4 Recent advancements in pharmacological research have highlighted the diverse biological activities. 5 , 6 Due to their intricate stereostructure and diverse biological activities, matrine-type alkaloids have garnered significant interest as promising targets for both pharmacological studies and synthetic chemistry endeavors.

The title compound was identified as (−)-flavesine H, the enantiomer of the previously reported (+)-flavesine H. 6  It belongs to the matrine-type alkaloids, distinguished by an open-loop ring D. Notably, the single-crystal structure of (+-)-flavesine H has not yet been reported. The C=O bond lengths 1.236(3)–1.277(3) Å, C–N bond lengths 1.314(3)–1.476(3) Å, C=C bond lengths 1.386(3)–1.408(3) Å and C–C bond lengths 1.507(3)–1.547(2) Å, which were derived from the title structure are within normal ranges. 7

Corresponding authors: Ding Luo and Guang-cun Wang, Department of Anesthesiology, The Fifth Affiliated Hospital of Jinan University, Heyuan 517000, P.R. China, E-mail: (D. Luo), (G.-c. Wang)

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

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

  3. Research funding: National Natural Science Foundation of China (No. 82304320).

References

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3. Sheldrick, G. M. Crystal Structure Refinement with Shelxl. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

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5. Zhang, Y. B.; Zhan, L. Q.; Li, G. Q.; Wang, F.; Wang, Y.; Li, Y. L.; Ye, W. C.; Wang, G. C. Dimeric Matrine-type Alkaloids from the Roots of Sophora flavescens and their anti–Hepatitis B Virus Activities. J. Org. Chem. 2016, 81, 6273–6280; https://doi.org/10.1021/acs.joc.6b00804.Search in Google Scholar PubMed

6. Zhang, Y. B.; Luo, D.; Yang, L.; Cheng, W.; He, L. J.; Kuang, G. K.; Li, M. M.; Li, Y. L.; Wang, G. C. Matrine-type Alkaloids from the Roots of Sophora flavescens and their Antiviral Activities against the Hepatitis B Virus. J. Nat. Prod. 2018, 81, 2259–2265; https://doi.org/10.1021/acs.jnatprod.8b00576.Search in Google Scholar PubMed

7. Li, W. Z.; Xu, L. H.; Liang, C. B.; Wang, H. B. Crystal Structure of (E)-N′-(4-((E)-3-(dimethylamino)acryloyl)-3-hydroxyphenyl)-N, N-Dimethylformimidamide, C14H19N3O2. Z. Kristallogr. N. Cryst. Struct. 2024, 239, 399–400; https://doi.org/10.1515/ncrs-2024-0017.Search in Google Scholar
Received: 2024-09-11
Accepted: 2024-10-18
Published Online: 2024-10-30
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)
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  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-2024-0366
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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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