Home Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
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Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO

  • Pholani Manana , Eric C. Hosten ORCID logo and Richard Betz ORCID logo EMAIL logo
Published/Copyright: October 5, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 1

Abstract

C9H13NO, orthorhombic, Pbcn (no. 60), a = 29.554(4) Å, b = 7.4930(11) Å, c = 8.2800(10) Å, V = 1833.6(4) Å3, Z = 8, Rgt(F) = 0.0737, wRref(F2) = 0.1646, T = 200 K.

CCDC no.: 2033457

The molecular 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:Colourless rod
Size:0.58 × 0.21 × 0.15 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.07 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:28.2°, 99%
N(hkl)measured, N(hkl)unique, Rint:14,634, 2212, 0.038
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1614
N(param)refined:106
Programs:Bruker [1], [,2], SHELX [3], WinGX/ORTEP [4], Mercury [5], PLATON [6]
Table 2:

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

AtomxYzUiso*/Ueq
O10.05354 (5)0.3666 (2)0.10111 (19)0.0433 (4)
H10.05110.45660.04120.065*
N10.04979 (7)0.3113 (3)0.4387 (2)0.0403 (5)
H710.0231 (8)0.323 (3)0.376 (3)0.048 (7)*
C10.13570 (7)0.3290 (3)0.1002 (3)0.0378 (5)
C20.13387 (10)0.2038 (4)−0.0231 (3)0.0521 (7)
H20.10560.1526−0.05240.063*
C30.17290 (12)0.1526 (5)−0.1041 (4)0.0740 (9)
H30.17130.0659−0.18760.089*
C40.21366 (11)0.2264 (5)−0.0640 (4)0.0754 (10)
H40.24040.1904−0.11900.090*
C50.21597 (9)0.3527 (5)0.0559 (4)0.0700 (9)
H50.24420.40580.08250.084*
C60.17713 (8)0.4028 (4)0.1380 (3)0.0530 (7)
H60.17910.48930.22160.064*
C70.09381 (7)0.3803 (3)0.1941 (3)0.0359 (5)
H70.09710.50590.23310.043*
C80.08810 (8)0.2571 (3)0.3392 (3)0.0391 (5)
H8A0.08340.13330.30110.047*
H8B0.11600.25930.40510.047*
C90.04157 (10)0.1851 (4)0.5710 (3)0.0581 (7)
H9A0.03960.06370.52740.087*
H9B0.01310.21570.62520.087*
H9C0.06650.19160.64870.087*

Source of material

The title compound was obtained commercially (ACROS). Crystals suitable for the diffraction study were obtained upon repeated slow sublimation of the compound at room temperature.

Experimental details

Carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic carbon atoms, C–H 0.99 Å for methylene groups, C–H 1.00 Å for the methine group) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C–C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite[2]), with U(H) set to 1.5Ueq(C).

The H atom of the hydroxyl groups was allowed to rotate with a fixed angle around the C–O bond to best fit the experimental electron density (HFIX 147 in the SHELX program suite[2]), with U(H) set to 1.5Ueq(O).

The nitrogen-bound H atom was located on a difference Fourier map and refined freely.

Comment

Chelate ligands have found widespread use in coordination chemistry due to the increased stability of coordination compounds they can form in comparison to monodentate ligands [7]. Aminols are particularly interesting in this aspect as they offer two different donor sites of markedly diverging acidity as potential bonding partners. Upon variation of the substituion pattern on the hydrocarbon backbone, the acidity of the two donor sites can be varied over a wide range and they may serve as probes for establishing the rules in which pKa range coordination to various central atoms of variable Lewis acidity can be observed. Furthermore, the spatial requirements of the substitution pattern can also be exploited to enable unusual coordination numbers. At the beginning of a study about a series of homo- and heteroleptic coordination compounds derived from simple vicinal aminols, the title compound was chosen as it only features one hydrogen atom on the nitrogen atom which we deemed to limit and simplify the coordination behaviour of this ligand and because very similar aminoles have been found to form stable coordination compounds with copper [8], [9], [10]. The crystal and molecular structures of similar aminoles have been reported earlier [11], [12], [13], [14], [15], [16], [17], [18].

The title compound is the N-methylated derivative of aminomethyl-benzyl alcohol. The C–O and C–N bond lengths are in good agreement with the most-common values found for other aminoles whose geometrical data has been deposited with the Cambridge Structural Database [19]. The two σ-donor sites are present in a nearly perfectly-staggered conformation with the corresponding O–C–C–N angle found at −61.2(2)°. The phenyl ring is orientated perpendicular to the nitrogen-containing side chain with the least-squares planes as defined by the carbon atoms of the aromatic moiety on the one hand and the non-hydrogen atoms of the CH2–CH2–NH–CH3 chain on the other hand enclosing an angle of 86.32(12)°.

In the crystal structure, classical hydrogen bonds of the O–H…N and N–H…O type are observed. The latter form a cooperative system. In terms of graph-set analysis [20], [21], the descriptor for these interactions is DD at the unary and R44(8) at the binary level. These hydrogen bonds connect the molecules to double strands that propagate along the crystallographic c axis. π–stacking is not a prominent feature in the crystal structure of the title compound as the shortest distance between two centers of gravity has been measured at 5.3122(19) Å.

Corresponding author: Richard Betz, Department of Chemistry, Nelson Mandela University, Summerstrand, Campus (South) University, Way Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa, E-mail:

Acknowledgments

The authors thank Mr. Matthias Schmid for helpful discussions.

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

  2. Research funding: None declared.

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

References

1. Bruker. APEX2; Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Search in Google Scholar

2. Bruker. SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2008.Search in Google Scholar

3. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.10.1107/S0108767307043930Search in Google Scholar PubMed

4. Farrugia, L. J. WinGX and ORTEP for windows: an update. J. Appl. Crystallogr. 2012, 45, 849–854; https://doi.org/10.1107/s0021889812029111.10.1107/S0021889812029111Search in Google Scholar

5. Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., Wood, P. A. Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 2008, 41, 466–470; https://doi.org/10.1107/s0021889807067908.10.1107/S0021889807067908Search in Google Scholar

6. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr. 2009, D65, 148–155; https://doi.org/10.1107/s090744490804362x.10.1107/S090744490804362XSearch in Google Scholar PubMed PubMed Central

7. Gade, L. H. Koordinationschemie, 1. Auflage; Wiley–VCH: Weinheim, 1998.10.1002/9783527663927Search in Google Scholar

8. Amano, Y., Osaki, K., Watanabe, T. On the study of the copper chelates of ephedrine and related compounds. II. the crystal structure of the bis-l-ephedrine copper(II) chelate benzene clathlate. Bull. Chem. Soc. Jpn. 1964, 37, 1363–1372; https://doi.org/10.1246/bcsj.37.1363.10.1246/bcsj.37.1363Search in Google Scholar

9. De Sousa, A. S., Hancock, R. D., Reibenspies, J. H. Structure of the copper(II) complex of the reinforced ligand N,-N′ bis(trans-2-hydroxycyclohexyl)-trans-cyclohexane-1,2-diamine and the metal-ion-size-based selectivity produced by cyclohexanediyl bridges. J. Chem. Soc., Dalton Trans. 1997, 2831–2836; https://doi.org/10.1039/a700759k.10.1039/a700759kSearch in Google Scholar

10. Bailey, N. A., Harrison, P. M., Mason, R. The structure of a bis-(+)- pseudoephedrine complex of copper(II). Chem. Commun. 1968, 559–560; https://doi.org/10.1039/c19680000559.10.1039/c19680000559Search in Google Scholar

11. Wikete, C., Wu, P., Zampella, G., De Gioia, L., Licini, G., Rehder, D. Glycine- and sarcosine-based models of vanadate-dependent haloperoxidases in sulfoxygenation reactions. Inorg. Chem. 2007, 46, 196–207; https://doi.org/10.1021/ic061534p.10.1021/ic061534pSearch in Google Scholar PubMed

12. Hossain, M. K., Haukka, M., Sillanpaa, R., Hrovat, D. A., Richmond, M. G., Nordlander, E., Lehtonen, A. Syntheses and catalytic oxotransfer activities of oxo molybdenum(VI) complexes of a new aminoalcohol phenolate ligand. Dalton Trans. 2017, 46, 7051–7060; https://doi.org/10.1039/c7dt00846e.10.1039/C7DT00846ESearch in Google Scholar PubMed

13. Wu, P., Santoni, G., Froba, M., Rehder, D. Modelling the sulfoxygenation activity of vanadate-dependent peroxidases. Chem. Biodivers. 2008, 5, 1913–1926; https://doi.org/10.1002/cbdv.200890179.10.1002/cbdv.200890179Search in Google Scholar PubMed

14. Kocakaya, S. O., Karakaplan, M., Scopelliti, R. Synthesis and crystal structure of a chiral lactam and three amino alcohols as potential protein tyrosine phosphates 1B inhibitors. Tetrahedron: Asymmetry 2017, 28, 1342–1349; https://doi.org/10.1016/j.tetasy.2017.09.014.10.1016/j.tetasy.2017.09.014Search in Google Scholar

15. Deshpande, S. H., Kelkar, A. A., Gonnade, R. G., Shingote, S. K., Chaudhari, R. V. Catalytic asymmetric transfer hydrogenation of ketones using [Ru(p-cymene)Cl2]2 with chiral amino alcohol ligands. Catal. Lett. 2010, 138, 231–238; https://doi.org/10.1007/s10562-010-0408-y.10.1007/s10562-010-0408-ySearch in Google Scholar

16. Wikete, C., Wu, P., Zampella, G., De Gioia, L., Lincini, G., Rehder, D. Glycine- and sarcosine-based models of vanadate-dependent haloperoxidases in sulfoxygenation reactions. Inorg. Chem. 2007, 46, 196–207; https://doi.org/10.1021/ic061534p.10.1021/ic061534pSearch in Google Scholar PubMed

17. Betz, R., Gerber, T., Schalekamp, H. 5-Amino-pentan-1-ol. Acta Crystallogr. 2011, E67, o1841; https://doi.org/10.1107/s1600536811024731.10.1107/S1600536811024731Search in Google Scholar PubMed PubMed Central

18. Betz, R., Gerber, T., Hosten, E. (3-Amino-phen-yl)methanol. Acta Crystallogr. 2011, E67, o2118; https://doi.org/10.1107/s1600536811029163.10.1107/S1600536811029163Search in Google Scholar PubMed PubMed Central

19. Allen, F. H. The Cambridge structural database: a quarter of a million crystal structures and rising. Acta Crystallogr. 2002, B58, 380–388; https://doi.org/10.1107/s0108768102003890.10.1107/S0108768102003890Search in Google Scholar PubMed

20. Bernstein, J., Davis, R. E., Shimoni, L., Chang, N.-L. Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew Chem. Int. Ed. Engl. 1995, 34, 1555–1573; https://doi.org/10.1002/anie.199515551.10.1002/anie.199515551Search in Google Scholar

21. Etter, M. C., MacDonald, J. C., Bernstein, J. Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr. 1990, B46, 256–262; https://doi.org/10.1107/s0108768189012929.10.1107/S0108768189012929Search in Google Scholar

Received: 2020-08-03
Accepted: 2020-09-23
Published Online: 2020-10-05
Published in Print: 2021-01-26

© 2020 Pholani Manana et al., published by De Gruyter, Berlin/Boston

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

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  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
https://doi.org/10.1515/ncrs-2020-0433
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-oxo-urs-12-en-28-oic acid, C30H46O3·1/6H2O
  4. The crystal structure of (3S,12R,20R,24R)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25–triol–ethyl acetate (4/1), C34H56O6⋅ 0.25(C4H8O2)
  5. A new polymorph of tetrakis(dimethylammonium) catena-poly[tetrakis(μ2-sulfato-κ2O:O′)dizinc(II)], Zn2C8H32N4O16S4
  6. Crystal structure of 10-oxysophoridine, C15H22N2O2
  7. The crystal structure of (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O4
  8. Synthesis, crystal structure and optical property of 1,6-bis(p-tolylthio)pyrene, C30H22S2
  9. The crystal structure of hexakis(2-(pyridin-2-ylamino)pyridin-1-ium) decavanadate(V) dihydrate, C60H64N18O30V10
  10. Preparation and crystal structure of a cationic olefin polymerization precatalyst: (1,7-bis(2,6–dichlorophenyl)-1,7-di-aza-4-oxo-heptan-1,4,7-triyl)dimethyl zirconium(IV), C18H20Cl4N2OZr
  11. The crystal structure of fac-tricarbonyl(4,4-dimethyl-2,2-dipyridyl-κ2N,N′)- (pyrazole-κN)rhenium(I) nitrate, C18H16O3N4Re
  12. Synthesis and crystal structure of hexaaquacopper(II) 2,5-dicarboxyterephthalate, C10H16O14Cu
  13. The crystal structure of (8R,10R,12R,14R)- 12-hydroxy-16-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)- 4,4,8,10,14-pentamethyltetradecahydro-3H- cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O5
  14. Structure of the mixed crystal (S)-(6-(bromo/chloro)-2-methoxy-2,6-dihydroquinolin-3-yl)(phenyl)methanol, C17H14Br0.5Cl0.5NO2
  15. The crystal structure of trans-tetraaqua-bis(4-acetylphenoxyacetato-κ1O)manganese(II), C20H26O12Mn
  16. Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  17. Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
  18. The crystal structure of dipentaerthritol hexanitrate, C10H16N6O19
  19. Crystal structure of N,N-diphenylformamide, C13H11NO
  20. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen- 1(2H)-one, C20H14F6O2
  21. Crystal structure of ortho-methoxy benzaldehyde, C8H8O2 – a second polymorph and deposition of 3D coordinates
  22. Crystal structure of catena-poly[diaqua-bis(μ2-2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O:O')-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O,O')yttrium(III)], C51H79O11Y
  23. Crystal structure of benzylthiouronium chloride, C8H11ClN2S
  24. Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4a′R,9a′S)-1-acetyl-5-chloro-3″-methyl-2,5″,9′-trioxo-1″-phenyl-1″,4a′,5″,9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4″-pyrazole]-3′-carboxylate, C36H32ClN3O7
  25. Crystal structure of 2-hydroxy-4-methoxy benzaldehyde, C8H8O3
  26. Crystal structure of poly[diaqua-(m3-3′,5′-dicarboxy-[1,1′-biphenyl]-3,4-dicarboxylato-K4O,O′:O″:O‴) cadmium(II)], C16H11O10Cd
  27. Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)} – water – acetone (1/1/8/2)
  28. Synthesis and crystal structure of bis{2-bromo-6-((E)-((4-((E)-1-(methoxy-imino)ethyl)phenyl)imino)methyl)phenolato- κ2N,O}zinc(II)-methanol(1/2), C65H60Br4N8O9Zn2
  29. Crystal structure of benzenesulphonic acid
  30. Crystal structure of N-benzyl-N-nicotinoyl-nicotine amide C19H15N3O2
  31. Crystal structure of poly[aqua(μ3-2,4-diamino-benzenesulfonato-κ4N:N′,O:O′)silver(I)], C12H18O8N4S2Ag2
  32. Crystal structure of 1,4-bis(methylpyridinium benzene) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C26H18N6NiS4
  33. Crystal structure of the Cu(II) complex chlorido-(6-oxo-2-phenyl-1,6-dihydropyrimidine-4-carboxylato-k2N,O)-(phenanthroline-k2N,N')copper(II), C23H15ClCuN4O3
  34. Crystal structure of phenarsazine chloride acetic acid solvate, C14H13AsClNO2
  35. Crystal structure of poly[aqua-(μ2-3,3′,4,5′-biphenyl tetracarboxylate- κ3O,O′:O′′) -(μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)zinc(II)], C27H18NO9Zn
  36. Crystal structure of catena-poly[(μ2-3-amino-benzenedisulfonato-κ2N:O)-bis (3-methyl-isoquinoline-κN)silver(I)], C26H24N3O3SAg
  37. Crystal structure of 2-((4-Aminophenyl)thio)acetic acid, C8H9NO2S
  38. Crystal structure of phenarsazine chloride dimethylsulfoxide solvate, C14H15AsClNOS
  39. Synthesis and crystal structure of 2-azido-N-phenylacetamide, C8H8N4O
  40. Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6
  41. Crystal structure of benzanthrone – a redetermination for correct molecular geometry and localization of hydrogen atoms
  42. Crystal structure of 4-bromobenzaldehyde – complete redetermination at 200 K, C7H5BrO
  43. Crystal structure and spectroscopic properties of chlorido{hydridotris[3-,5-dimethylpyrazol-1-yl-κN3]borato}(3-,5-dimethylpyrazol-1-yl-κN)copper(II), C20H30BClCuN8
  44. The crystal structure of 4-((2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl)benzonitrile, C22H20N2O
  45. Crystal structure of 4-ethyl-3-phenylisoquinolin-1(2H)-one, C17H15NO
  46. Crystal structure of (tricyclohexylphosphane-κP)-[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-k1S]gold(I), C26H40AuFNOPS
  47. Crystal structure of (3S,8R,10R,12R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H54O4
  48. The crystal structure of 2-[(S)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a- tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  49. Crystal structure of {hydridotris[3-(t-butyl)-5-isopropylpyrazol-1-yl-κN3]borato}thallium(I), C30H52BN6Tl
  50. Synthesis and crystal structure of 1-octyl-3-phenylquinoxalin-2(1H)-one, C22H26N2O
  51. The crystal structure of 2,6-difluorophenol, C6H4F2O
  52. 4-(9H-Fluoren-9-yl)-4-methylmorpholin-4-ium bromide, C18H20BrNO
  53. The crystal structure of 2,4-dimethylimidazole monohydrate, C5H10N2O
  54. The crystal structure of 1,2-dimethylimidazole, C5H8N2
  55. The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 – a second polymorph
  56. The crystal structure of 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate chloride monohydrate, C14H15N4O5S2Cl
  57. The crystal structure of butyrylferrocene, C14H16FeO
  58. The crystal structure of bi-1,1′-cyclopentane-1,1′-diol, C10H18O2
  59. The crystal structure of 2-iso-propylimidazole, C6H10N2
  60. The crystal structure of aqua-tris (1,3-diphenylpropane-1,3-dionato-κ2O,O′)-lanthanum(III), C45H35LaO7
  61. Crystal structure of (3E,5E)-3,5-bis-4-methoxy-3-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  62. The crystal structure of 3,5-dichloro-6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, C6Cl2N4O5
  63. Crystal structure of carbonyl(2-methylquinolin-8-olato-κ2N,O)(triphenylarsine-κAs)rhodium(I), C29H23AsNO2Rh
  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
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