Home Crystal structure of 6-cyclohexyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl nitrate, C20H23O3N2Bi
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Crystal structure of 6-cyclohexyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl nitrate, C20H23O3N2Bi

  • Nianyuan Tan EMAIL logo , Shuisheng Wu , Yang Huiqiong , Donghui Lan , Chak-Tong Au and Bing Yi EMAIL logo
Published/Copyright: February 1, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 3

Abstract

C20H23O3N2Bi, monoclinic, P21/n (no. 14), a = 10.6897(5) Å, b = 10.5590(5) Å, c = 17.4099(9) Å, β = 105.491(2)°, V = 1893.71(16) Å3, Z = 4, Rgt(F) = 0.0253, wR(F2) = 0.0576, T = 296(2) K.

CCDC no.: 933953

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.05 × 0.04 × 0.03 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:9.33 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.5°, 98%
N(hkl)measured, N(hkl)unique, Rint:14351, 4174, 0.034
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3516
N(param)refined:235
Programs:Bruker programs [1], SHELX programs [2], [3], Olex2 [2]
Table 2:

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

AtomxyzUiso*/Ueq
Bi10.99740(2)0.27546(2)0.04107(2)0.02798(6)
N10.7606(3)0.2827(3)0.0321(2)0.0278(7)
N21.2999(4)0.2434(4)0.0921(3)0.0468(10)
O11.2198(3)0.3143(4)0.1148(2)0.0489(8)
O21.2588(4)0.1543(4)0.0483(3)0.0654(11)
O31.4140(4)0.2673(6)0.1160(3)0.104(2)
C10.9601(4)0.4611(4)0.0942(2)0.0284(8)
C21.0537(4)0.5374(4)0.1441(2)0.0341(9)
H21.1404890.5130980.1572020.041*
C31.0187(5)0.6488(4)0.1742(3)0.0408(11)
H31.0808230.6972090.2097030.049*
C40.8908(5)0.6878(5)0.1515(3)0.0471(12)
H40.8672520.7643620.1700840.057*
C50.7980(5)0.6137(4)0.1012(3)0.0433(11)
H50.7119240.6403680.0864600.052*
C60.8313(4)0.5003(4)0.0726(2)0.0331(9)
C70.7285(4)0.4196(4)0.0175(3)0.0366(10)
H7A0.6445190.4370100.0265260.044*
H7B0.7238420.440334−0.0375200.044*
C110.9738(4)0.1542(4)0.1411(2)0.0304(9)
C121.0714(4)0.0771(4)0.1870(3)0.0401(10)
H121.1535240.0779460.1783040.048*
C131.0471(5)−0.0001(5)0.2447(3)0.0466(11)
H131.112556−0.0517720.2747770.056*
C140.9258(5)−0.0011(5)0.2582(3)0.0464(12)
H140.909919−0.0524170.2979850.056*
C150.8275(4)0.0740(4)0.2129(3)0.0401(10)
H150.7453230.0716210.2213780.048*
C160.8517(4)0.1535(4)0.1541(2)0.0294(8)
C170.7498(4)0.2458(4)0.1123(3)0.0341(10)
H17A0.6649000.2086300.1069650.041*
H17B0.7559400.3213170.1447920.041*
C210.6808(4)0.1959(4)−0.0309(2)0.0293(9)
H210.7018680.108994−0.0120140.035*
C220.7152(4)0.2078(5)−0.1097(3)0.0414(11)
H22A0.8071850.191697−0.1012810.050*
H22B0.6977920.293666−0.1295090.050*
C230.6381(4)0.1156(5)−0.1716(3)0.0435(11)
H23A0.6570750.131380−0.2222100.052*
H23B0.6651580.029779−0.1553550.052*
C240.4933(4)0.1273(5)−0.1824(3)0.0454(11)
H24A0.4637300.208979−0.2057800.054*
H24B0.4485880.062045−0.2187110.054*
C250.4604(4)0.1142(5)−0.1037(3)0.0435(11)
H25A0.4825390.029721−0.0825790.052*
H25B0.3678830.126333−0.1115710.052*
C260.5350(4)0.2120(5)−0.0442(3)0.0416(11)
H26A0.5097700.296561−0.0643110.050*
H26B0.5131880.2024970.0060640.050*

Source of material

The compound C6H11N(CH2C6H4)2BiCl is prepared by the literature known synthesis [5]. To a solution of C6H11N(CH2C6H4)2BiCl (0.274 g, 0.5 mmol) in 20 mL CH2Cl2, a solution of AgNO3 (0.085 g, 0.5 mmol) in 10 mL distilled water was added. The mixture was stirred in the dark at room temperature for 12 h and then filtered. The organic phase was separated from aqueous phase and dried over anhydrous Na2SO4. After removal of the solvent in vacuum, the compound C6H11N(CH2C6H4)2BiNO3 was obtained. Crystals suitable for X-ray diffraction analysis were obtained by crystallization from CH2Cl2/n-hexane solution. 1H NMR (400 MHz, CDCl3, TMS): δ = 8.19 (2H, s), 7.54 (4H, dd, J = 14.8, 7.6 Hz), 7.33 (2H, t, J = 7.6 Hz), 4.53 (2H, d, J = 15.2 Hz), 4.32 (2H, d, J = 15.2 Hz), 2.97 (1H, t, J = 11.2 Hz), 2.07 (2H, d, J = 11.6 Hz), 1.90 (2H, d, J = 12.8 Hz), 1.69 (1H, d, J = 12.8 Hz), 1.44−1.26 (4H, m), 1.17–1.08 (1H, m) ppm; 13C NMR (CDCl3, 100 MHz, TMS): δ = 150.65, 137.80, 131.10, 128.39, 128.15, 65.75, 62.40, 31.20, 25.62, 25.36 ppm.

Experimental details

All H atoms were generated geometrically and refined using the riding model, with C—H = 0.93 Å for aryl and 0.97 Å for methylene H atoms, respectively. Uiso(H) set to 1.2Ueq(C) for all H atoms.

Comment

The interest in the chemistry of hypervalent organobismuth compounds with intramolecular N, O, S → Bi interactions has increased in recent years owing to their fascinating chemistry, structure and uses in organic synthesis, catalysis and medicine [5], [6], [7], [8], [9], [10], [11], [12], [13]. As part of our work on hypervalent organobismuth compounds with intramolecular N, O, S → Bi interactions, we report herein the crystal structure of a hypervalent organobismuth nitrate with intramolecular N → Bi coordinations.

In the molecular structure of organobismuth nitrate (cf. the figure), C6H11N(CH2C6H4)2BiNO3, the N → Bi coordination is observed, and the Bi(1)—N(1) distance [2.495(3) Å] is shorter than those of the organobismuth chloride and triphenylgermylpropionate with same framework, e.g. C6H11N(CH2C6H4)2BiCl (2.517(4) Å) [5] and C6H11N(CH2C6H4)2BiOC(O)CH2CH2GePh3 (2.563(3) Å) [5], while this distance is longer than those of the organobismuth perfluorooctanesulfonate and tetrafluoroborate with same framework, i.e. C6H11N(CH2C6H4)2BiOSO2C8F17 (2.397(5) Å) [6] and C6H11N(CH2C6H4)2BiBF4 (2.394(8) Å) [7]. The geometry around the central Bi atom can be described as a distorted pseudo-trigonal bipyramid. The N(1) and O(1) atoms occupy at the apical positions, and both the C(1) and C(11) atoms at the equatorial positions along with a lone electron pair of bismuth. The nitrate group in the title compound can be considered as acting as an asymmetric bidentate ligand (cf. the figure). One O atom of nitrate group is covalently bound to the bismuth [Bi(1)—O(1) 2.416(3) Å], while the other O atom is weakly coordinated to the bismuth [Bi(1)—O(2) 3.0451(4) Å vs. rvdW (Bi,O) 3.80 Å] [14]. Similar Bi—O distances were found for nitrate ligands in the related [2,6-(Me2NCH2)2C6H3]Bi(NO3)2 [8], [2-(Me2NCH2)C6H4]2BiNO3 [9], C6H5CH2N(CH2C6H4)2BiNO3 [10], O(CH2C6H4)2BiNO3 [12], S(CH2C6H4)2BiNO3 [13]. Taking in account these contacts and the increased coordination number of the bismuth, the title compound might be described as 12-Bi-5 hypervalent species [15], [16], [17].

Acknowledgements

The work was supported by the Scientific Research Fund of Hunan Province Education Department (No. 15A041), and Talent Research Startup Fund of Hunan Institute of Engineering (Nos. 14006 and 16RC001).

References

1. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2009).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

3. Sheldrick, G. M.: SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

4. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar

5. Zhang, X. W.; Xia, J.; Yan, H. W.; Luo, S. L.; Yin, S. F.; Au, C. T.; Wong, W. Y.: Synthesis, structure, and in vitro antiproliferative activity of cyclic hypervalent organobismuth(III) chlorides and their triphenylgermylpropionate derivatives. J. Organomet. Chem. 694 (2009) 3019–3026.10.1016/j.jorganchem.2009.05.003Search in Google Scholar

6. Zhang, X. W.; Yin, S. F.; Qiu, R. H.; Xia, J.; Dai, W. L.; Yu, Z. Y.; Au, C. T.; Wong, W. Y.: Synthesis and structure of an air-stable hypervalent organobismuth(III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water. J. Organomet. Chem. 694 (2009) 3559–3564.10.1016/j.jorganchem.2009.07.018Search in Google Scholar

7. Zhang, X. W.; Qiu, R. H.; Tan, N. Y.; Yin, S. F.; Xia, J.; Luo, S. L.; Au, C. T.: Air-stable hypervalent organobismuth(III) tetrafluoroborate as effective and reusable catalyst for the allylation of aldehyde with tetraallyltin. Tetrahedron Lett. 51 (2010) 153–156.10.1016/j.tetlet.2009.10.104Search in Google Scholar

8. Breunig, H. J.; Nema, M. G.; Silvestru, C.; Soran, A.; Varga, R. A.: Organobismuth compounds with the pincer ligand 2,6-(Me2NCH2)C6H3: monoorganobismuth(III) carbonate, sulfate, nitrate, and a diorganobismuthenium(III) salt. Dalton Trans. 39 (2010) 11277–11284.10.1039/c0dt00927jSearch in Google Scholar PubMed

9. Nema, M. G.; Breunig, H. J.; Soran, A.; Silvestru, C.: Diorganobismuth(III) compounds with the pendant arm 2-(Me2NCH2)C6H4 ligand – isothiocyanate, trifluoracetate and nitrate. J. Organomet. Chem. 705 (2012) 23–29.10.1016/j.jorganchem.2012.01.011Search in Google Scholar

10. Toma, A.; Ra t, C. I.; Pavel, O.; Hardacre, C.; Rüffer, T.; Lang, H.; Mehring, M.; Silvestru, A.; Pârvulescu, V.: Heterocyclic bismuth(III) compounds with transannular N→Bi interactions as catalysts for the oxidation of thiophenol to diphenyldisulfide. Catal. Sci. Technol. 7 (2017) 5343–5353.10.1039/C7CY00521KSearch in Google Scholar

11. Tan, N. Y.; Dang, L. M.; Lan, D. H.; Wu, S. S.; Au, C. T.; Yi, B.: Crystal structure of bis{5H-dibenzo[c,f][1,5]oxabismocin-12(7H)-yl} carbonate, C29H24O5Bi2. Z. Kristallogr. NCS 233 (2018) 875–877.10.1515/ncrs-2018-0067Search in Google Scholar

12. Liu, Y. P.; Lei, J.; Tang, L. W.; Peng, Y.; Au, C. T.; Chen, Y.; Yin, S. F.: Studies on the cytotoxicity and anticancer performance of heterocyclic hypervalent organobismuth(III) compounds. Eur. J. Med. Chem. 139 (2017) 826–835.10.1016/j.ejmech.2017.08.043Search in Google Scholar PubMed

13. Toma, A.; Ra t, C. I.; Silvestru, A.; Rüffer, T.; Lang, H.; Mehring, M.: Heterocyclic bismuth(III) compounds with transannular S→Bi interactions. An experimental and theoretical approach. J. Organomet. Chem. 806 (2016) 5–11.10.1016/j.jorganchem.2016.01.019Search in Google Scholar

14. Emsley, J.: Die Elemente. Walter de Gruyter, Berlin (1994).10.1515/9783110857054Search in Google Scholar

15. Perkins, C. W.; Martin, J. C.; Arduengo, A. J.; Lau, W.; Alegria, A.; Koch, K.: The N-X-L nomenclature system has been described previously: N valence shell electrons about a central atom X with L ligands. J. Am. Chem. Soc. 102 (1980) 7753–7759.10.1021/ja00546a019Search in Google Scholar

16. Tan, N.; Zhang, X.: 6-Cyclohexyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl(N→Bi) trifluoromethanesulfonate. Acta Crystallogr. E67 (2011) m252.10.1107/S1600536811002510Search in Google Scholar PubMed PubMed Central

17. Zhang, X.-W.; Fan, T.: 6-Phenyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl perchlorate. Acta Crystallogr. E67 (2011) m875.10.1107/S1600536811021039Search in Google Scholar PubMed PubMed Central

Received: 2018-11-17
Accepted: 2019-01-14
Published Online: 2019-02-01
Published in Print: 2019-03-26

©2019 Nianyuan Tan 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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  54. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)nickel(II), C16H22O10Ni
  55. Crystal structure of ajacisine D monohydrate, C30H44N2O9
  56. The crystal structure of (E)-4-(1-(2-aminophenylimino)ethyl)benzene-1,3-diol, C14H14N2O2
  57. Crystal structure of poly[(μ4-(4H-1,2,4-triazol-4-yl)phenyl)acetato-κ4N,N′,O,O′)(formiato-κ1O)cobalt(II)], C11H9CoN3O4
  58. The crystal structure of bis tetrabutylammonium bis(μ3-2,2,2-tri(hydroxymethyl)ethyl-4-((3-methoxy-3-oxopropyl)amino)-4-oxobutanoato)-(μ6-oxido)-hexakis(μ2-oxido)-hexaoxido-hexavanadium(V), C58H112N4O29V6
  59. Crystal structure of (N-benzylpropane-1,3-diamine-κ2N, N′)(2,2′-bipyridine-κ2N,N′)platinum(II) chloride, C20H24Cl2N4Pt
  60. Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-2-amine, C23H16ClN5O
  61. Crystal structure of poly-[(μ2(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N: O:O′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C18H14CuN4O6S
  62. Crystal structure of poly-[(μ2-(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N:O:O′)(μ2-4,4′-bipyridine-κ2N:N′) nickel(II)], C18H14NiN4O6S
  63. Crystal structure of N-((3R,10S,13S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-N-methylbenzamide, C31H48N2O
  64. The crystal structure of dichloroido(1,3-bis(2,6-dimethyl-phenyl)-1H-3l4-imidazol-2-yl)(2-methyl-4,5-dihydrooxazol-κN)palladium(IV)-water (1/1), C23H29Cl2N3O2Pd
  65. Crystal structure of catena-poly[dibromido-{μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O}zinc(II)], C34H32Br4N8O2Zn2
  66. Crystal structure of diaqua-dichlorido-bis(μ2-2-(((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)dicobalt(II), C36H36Cl2N6O6Co2
  67. Crystal structure of catena-poly[diaqua-(μ2-1,2-bis(4-pyridinyl)ethyane-κ2N:N′)-(μ2–pyridazine-4,5-dicarboxylato-κ2O:O′)]dizinc(II) dihydrate, C12H12ZnN3O6
  68. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro)diazene oxide, C12H6Cl2N4O5
  69. Crystal structure of 2-isopropylthioxanthone, C16H14OS
  70. Crystal structure of methyl 2-(4-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C19H17N5O2
  71. Crystal structure of 4,4-dimethyl-2-(trifluoromethyl)-4,5-dihydro-1H-imidazole, C6H9F3N2
  72. Crystal structure of N-methylanilinium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate, C22H21NO8S
  73. Crystal structure of methyl 4-acetoxybenzoate, C10H10O4
  74. Crystal structure of catena-poly[(bis(μ-1,1′-[(5-methoxy-2,4,6-trimethyl-1,3-phenylene)bis(methylene)]bis(1H-1,2,4-triazole)-κ2N:N′)-bis(isothiocyanato-κN)manganese(II)], C34H40MnN14O2S2
  75. Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
https://doi.org/10.1515/ncrs-2018-0507
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of poly[aqua-μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)-μ4-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-κ4O:O′:O′′:O′′′)manganese(II)], C52H40N2O10Mn2
  3. Crystal structure of bis[2-(((3-aminopropyl)imino)methyl)-4-nitro-phenolato-κ3N,N′,O]nickel(II), C20H24N6NiO6
  4. Synthesis and crystal structure of bis{2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl) phenolato-κ2N,O}cobalt(II) — ethanol (1/1), C34H36CoN4O5
  5. Crystal structure of 1-(4-{2,5-dichloro-3-hydroxy-4-[4-(1-methoxyimino-ethyl)-phenylamino]-6-methyl-phenylamino}-phenyl)-ethanone O-methyl-oxime, C24H22Cl2N4O4
  6. The pseudosymmetric crystal structure of 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane dimethyl carbonate (2/3), C21H30N24O33
  7. Crystal structure of (1,4-diazepane)4CuII2(μ-Cl)10CuI6, C20H48Cl10Cu8N8
  8. Crystal structure of methyl 2,7,7-trimethyl-4-(3-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H23NO3S
  9. Crystal structure of methyl 2-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H13N3O2
  10. Crystal structure of (1S,3aR,3bR,10aR,10bR,12aR)-8-amino-3a,3b,6,6,10a-pentamethyl-1-((S)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-cyclopenta[7,8]phenanthro[2,3-d]thiazol-12-ol – a panaxadiol dervative, C31H50N2O2S
  11. Crystal structure of bis[(((4-fluorophenyl)amino)methyl)triphenylphosphonium] tetrachloridocobaltate(II), C50H44Cl4CoF2N2P2
  12. Crystal structure of 5,4′-dihydroxy-7,3′-dimethoxyflavanone, C17H16O6
  13. Crystal structure of 3-methyl-cyclobis(1-(1,1′-ferrocenylmethyl)-4-butyl-1H-1,2,3-triazole) tetrafluoroborate, C21H25FeN6⋅BF4
  14. Crystal structure of 3-(2-diethylaminoethyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C14H19N3OS
  15. Crystal structure of 2-(bis(3,5-dimethylphenyl) ((methyldiphenylsilyl)oxy)methyl) pyrrolidine, C34H39NOSi
  16. The crystal structure of 1,4-dinitro-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O12
  17. Crystal structure of rac-3,6-dimethyl-5-(prop-1-en-2-yl)-6-vinyl-1,4,5,6-tetrahydro-2H-indol-2-one, C15H19NO
  18. Crystal structure of (Cu0.51In0.49)tet[Cr1.74In0.26]octSe4 selenospinel, Cu0.51In0.75Cr1.74Se4
  19. Crystal structure of 7-hydroxy-5-methoxy-4,6-dimethylisobenzofuran-1(3H)-one, C11H12O4
  20. Crystal structure of trans-tetrakis(acetonitrile-κN)bis(triphenylphosphine-κP)ruthenium(II) dihexafluorophosphate - dichloroform (1/2), C46H44Cl6F12N4P4Ru
  21. Crystal structure of 2-((4-nitrophenyl)thio)ethan-1-ol, C8H9NO3S
  22. Crystal structure of diaqua-dichlorido-bis(μ3-6,6′-(hydrazine-1,2-diylidenebis(methanylylidene))bis(2-methoxyphenolato)κ6O,N:N′,O′,O′:O′′)trizinc(II) - ethanol (1/2), C36H44Cl2N4O12Zn3
  23. Crystal structure of the co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-chlorobenzoic acid (2/1), C35H25ClO10S4
  24. The crystal structure of 4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol, C15H11ClFN3O2
  25. Crystal structure of ethyl (E)-1-(3-ethoxy-3-oxoprop-1-en-1-yl)-2-(4-nitrophenyl)-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate, C23H23N3O6
  26. Crystal structure of (E)-2-(4-cyanophenyl)ethenesulfonyl fluoride, C9H6FNO2S
  27. Crystal structure of bis(4-bromo-2-(((3-chloropropyl)imino)methyl)phenolato-κ2N,O)-oxidovanadium(IV), C20H20Br2Cl2N2O3V
  28. The crystal structure of 1,1,1,3,3,3-hexaphenyldistannoxane – 2,2′-bipyridine (1/1), C46H38N2OSn2
  29. Crystal structure of coordination polymer catena-poly[diaqua-(2,6-dichloropyridine-4-carboxyliato-κ2O,O′)-bis(μ2-2,6-dichloropyridine-4-carboxyliato-κ2O:O′)terbium(III), C18H10Cl6N3O8Tb
  30. The crystal structure of 4-((2-(4,5-dihydro-1,5-diphenyl-1H-pyrazol-3-yl)anthracen-10-yl) methyl)morpholine, C34H31N3O
  31. The crystal structure of bis(N,N-dimethylformamide-κO)-tetrakis(9H-xanthene-9-carboxylic-carboxylate-κ2O:O′)dicopper(II) - acetonitrile (1/2), C66H56Cu2N4O14
  32. Crystal structure of trans-dichlorido-(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)-(5-methyl-3,4-dihydro-2H-pyrrole-κN)palladium(II), C25H31Cl2N3OPd
  33. Crystal structure of 8,8′-di-p-tolyl-8′H-7,8′-biacenaphtho[1,2-d]imidazole, C40H26N4
  34. The crystal structure of 3-amino-(2,4-dioxopent-3-yl)-4,5-dihydro-1,2,4-triazinium nitrate, C8H13N5O5
  35. Crystal structure of 4,4′,5,5′-tetraphenyl-2,2′-di-p-tolyl-2′H-1,2′-biimidazole, C44H34N4
  36. Halogen bonds in the crystal structure of 2-bromo-1,10-phenanthroline – 1,4-diiodotetrafluorobenzene (2/1), C30H14Br2F4I2N4
  37. Crystal structure of tris(1-phenyl-1,2-propanedione-2-oximato-κ2N,O)cobalt(III), C27H24N3O6Co
  38. Crystal structure of chlorido-(6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(3-methoxyphenolato)-κ4O,N,N′,O′)iron(III), C22H18ClN2FeO4
  39. Crystal structure of bis(μ2-1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-olato-κ3O,O′:O′)-bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-olato-κ2O,O)-bis(ethyl acetate-κO)dicadmium(II), C88H64Cl4N8O12S4Cd2
  40. Crystal structure of catena-poly[dichlorido-(μ2-3-(2-pyridyl)-4-(4-pyridyl)-5-(3-pyridyl)-1,2,4-triazole-κ2N:N′)] copper(II), C17H12N6Cl2Cu
  41. Crystal structure of dichlorido-([2,2′:6′,2′′-terpyridine]-4′-carboxylic acid-κ3N,N′,N′′)copper(II) monohydrate, C16H13Cl2CuN3O3
  42. Crystal structure of triethylammonium(5-carboxypyridine-2-thiolato-κ2N,S)-bis(dimethylsulfoxide-κ1S)-(6-sulfidonicotinato-κ2N,S)ruthenium(II) trihydrate, C22H41N3O9RuS4
  43. The crystal structure of poly[(μ5-2,5-dicarboxy-benzoato-κ4O:O:O′:O′′,O′′′)silver(I)], C9H5AgO6
  44. Crystal structure of (E)-1-(thiophen-2-yl)-N-(5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine, C25H19N3S3Sn
  45. Crystal structure of diaqua-bis(3,5-dichloroisonicotinato-κ1O)-bis(1,3-di(pyridin-4-yl)propane-κ1N)cobalt(II), C38H36Cl4N6O6Co
  46. Crystal structure of dodecaaqua-bis(μ2-4,4′-bipyridine-κ2N:N′)-bis(4,4′-((5-carboxylato-1,3-phenylene)bis(oxy))dibenzoato-κ1O)tricopper(II) - water (1/4), C62H70Cu3N4O32
  47. Crystal structure of bis(5-methoxy-2-(((2-oxidoethyl)imino)methyl)phenolate-κ3O,N,O′)manganes(IV), C20H22N2O6Mn
  48. Crystal structure of tetramethylammonium (2-(3-ethoxy-2-oxidobenzylidene)-1-(2-hydroxybenzoyl)hydrazin-1-ido-κ3N,N′,O)cobalt(III), C36H40N5O8Co
  49. Crystal structure of 6-cyclohexyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl nitrate, C20H23O3N2Bi
  50. Crystal structure of (E)-N-((2S,3S,4R,10R,13S, 17S)-17-(1-(dimethylamino) ethyl)-2,4-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide, C24H48N2O3
  51. Crystal structure of (E)-2-((4-chlorophenyl)(phenyl)methylene)hydrazine-1-carbothioamide, C14H12ClN3S
  52. Crystal structure of 1-benzyl-3-cyano-6-phenyl-1,2-dihydropyridine, C19H16N2
  53. Isolation and crystal structure of 4-((2-(methoxycarbonyl)phenyl)amino)-2-methyl-4-oxobutanoic acid from Delphinium Grandiflorum, C13H15N1O5
  54. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)nickel(II), C16H22O10Ni
  55. Crystal structure of ajacisine D monohydrate, C30H44N2O9
  56. The crystal structure of (E)-4-(1-(2-aminophenylimino)ethyl)benzene-1,3-diol, C14H14N2O2
  57. Crystal structure of poly[(μ4-(4H-1,2,4-triazol-4-yl)phenyl)acetato-κ4N,N′,O,O′)(formiato-κ1O)cobalt(II)], C11H9CoN3O4
  58. The crystal structure of bis tetrabutylammonium bis(μ3-2,2,2-tri(hydroxymethyl)ethyl-4-((3-methoxy-3-oxopropyl)amino)-4-oxobutanoato)-(μ6-oxido)-hexakis(μ2-oxido)-hexaoxido-hexavanadium(V), C58H112N4O29V6
  59. Crystal structure of (N-benzylpropane-1,3-diamine-κ2N, N′)(2,2′-bipyridine-κ2N,N′)platinum(II) chloride, C20H24Cl2N4Pt
  60. Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-2-amine, C23H16ClN5O
  61. Crystal structure of poly-[(μ2(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N: O:O′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C18H14CuN4O6S
  62. Crystal structure of poly-[(μ2-(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N:O:O′)(μ2-4,4′-bipyridine-κ2N:N′) nickel(II)], C18H14NiN4O6S
  63. Crystal structure of N-((3R,10S,13S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-N-methylbenzamide, C31H48N2O
  64. The crystal structure of dichloroido(1,3-bis(2,6-dimethyl-phenyl)-1H-3l4-imidazol-2-yl)(2-methyl-4,5-dihydrooxazol-κN)palladium(IV)-water (1/1), C23H29Cl2N3O2Pd
  65. Crystal structure of catena-poly[dibromido-{μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O}zinc(II)], C34H32Br4N8O2Zn2
  66. Crystal structure of diaqua-dichlorido-bis(μ2-2-(((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)dicobalt(II), C36H36Cl2N6O6Co2
  67. Crystal structure of catena-poly[diaqua-(μ2-1,2-bis(4-pyridinyl)ethyane-κ2N:N′)-(μ2–pyridazine-4,5-dicarboxylato-κ2O:O′)]dizinc(II) dihydrate, C12H12ZnN3O6
  68. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro)diazene oxide, C12H6Cl2N4O5
  69. Crystal structure of 2-isopropylthioxanthone, C16H14OS
  70. Crystal structure of methyl 2-(4-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C19H17N5O2
  71. Crystal structure of 4,4-dimethyl-2-(trifluoromethyl)-4,5-dihydro-1H-imidazole, C6H9F3N2
  72. Crystal structure of N-methylanilinium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate, C22H21NO8S
  73. Crystal structure of methyl 4-acetoxybenzoate, C10H10O4
  74. Crystal structure of catena-poly[(bis(μ-1,1′-[(5-methoxy-2,4,6-trimethyl-1,3-phenylene)bis(methylene)]bis(1H-1,2,4-triazole)-κ2N:N′)-bis(isothiocyanato-κN)manganese(II)], C34H40MnN14O2S2
  75. Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
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