Home The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3
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The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3

  • Chen Zhen ORCID logo , Sun Yanwen EMAIL logo and Meng Yingying
Published/Copyright: October 24, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 6

Abstract

C26H31BrN2O3, orthorhombic, P212121 (no. 19), a = 11.01(1) Å, b = 13.227(12) Å, c = 16.458(14) Å, V = 2397(4) Å3, Z = 4, R gt(F) = 0.0367, wR ref(F 2) = 0.0775, T = 298(2) K.

CCDC no.: 2160192

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: Colorless block
Size: 0.20 × 0.15 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.75 mm−1
Diffractometer, scan mode: Bruker Smart Apex II, φ and ω
θ max, completeness: 27.7°, >99%
N(hkl)measured, N(hkl)unique, R int: 17,705, 5536, 0.035
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3657
N(param)refined: 302
Programs: Bruker [1], Olex2 [2], SHELX [3, 4], Diamond [5]
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.76167 (4) 0.87996 (3) 0.22192 (3) 0.07424 (18)
O1 0.4379 (2) 1.26682 (16) 0.16071 (15) 0.0495 (6)
O2 0.3263 (2) 1.02571 (18) 0.05528 (15) 0.0568 (7)
O3 0.3703 (2) 0.87087 (16) 0.10886 (13) 0.0465 (6)
N1 0.5625 (2) 1.13180 (19) 0.17696 (16) 0.0393 (7)
H1 0.5616 1.0673 0.1837 0.047*
N2 0.3660 (2) 1.00455 (17) 0.18860 (16) 0.0366 (6)
C1 0.6514 (4) 1.1138 (3) −0.0233 (2) 0.0710 (12)
H1A 0.5747 1.0782 −0.0186 0.085*
H1B 0.6682 1.1234 −0.0806 0.085*
C2 0.6395 (4) 1.2196 (3) 0.0185 (2) 0.0555 (10)
H2A 0.6675 1.2711 −0.0190 0.067*
H2B 0.5544 1.2326 0.0297 0.067*
C3 0.7093 (3) 1.2287 (2) 0.0957 (2) 0.0411 (9)
C4 0.6781 (3) 1.1765 (2) 0.1665 (2) 0.0367 (8)
C5 0.7656 (3) 1.1500 (2) 0.2228 (2) 0.0441 (8)
H5 0.7429 1.1152 0.2695 0.053*
C6 0.8860 (3) 1.1744 (3) 0.2108 (2) 0.0509 (9)
C7 0.9103 (4) 1.2458 (3) 0.1505 (3) 0.0599 (12)
H7 0.9867 1.2756 0.1480 0.072*
C8 0.8239 (4) 1.2726 (3) 0.0950 (3) 0.0543 (11)
H8 0.8421 1.3212 0.0560 0.065*
C9 0.9824 (4) 1.1090 (4) 0.2487 (3) 0.0742 (12)
H9A 0.9565 1.0901 0.3030 0.089*
H9B 1.0564 1.1483 0.2539 0.089*
C10 1.0110 (4) 1.0099 (3) 0.1989 (3) 0.0732 (13)
H10A 1.0947 1.0122 0.1806 0.088*
H10B 1.0024 0.9519 0.2345 0.088*
C11 0.9294 (3) 0.9964 (3) 0.1265 (2) 0.0473 (9)
C12 0.8144 (3) 0.9567 (2) 0.1299 (2) 0.0417 (8)
C13 0.7263 (3) 0.9820 (2) 0.0744 (2) 0.0430 (9)
H13 0.6497 0.9527 0.0781 0.052*
C14 0.7502 (4) 1.0503 (2) 0.0135 (2) 0.0473 (9)
C15 0.8711 (4) 1.0716 (3) −0.0014 (2) 0.0548 (11)
H15 0.8933 1.1046 −0.0490 0.066*
C16 0.9582 (3) 1.0443 (3) 0.0537 (3) 0.0526 (10)
H16 1.0391 1.0582 0.0421 0.063*
C17 0.4534 (3) 1.1784 (2) 0.17765 (19) 0.0352 (8)
C18 0.3495 (3) 1.1118 (2) 0.20681 (18) 0.0353 (7)
H18 0.2731 1.1354 0.1828 0.042*
C19 0.3389 (3) 1.1128 (3) 0.2997 (2) 0.0498 (9)
H19Aa 0.3810 1.1707 0.3223 0.060*
H19Ba 0.2544 1.1154 0.3162 0.060*
H19Cb 0.4151 1.1341 0.3238 0.060*
H19Db 0.2758 1.1594 0.3165 0.060*
C21 0.3716 (4) 0.9406 (2) 0.2608 (2) 0.0510 (9)
H21Aa 0.4361 0.8909 0.2563 0.061*
H21Ba 0.2951 0.9060 0.2699 0.061*
H21Cb 0.4550 0.9261 0.2758 0.061*
H21Db 0.3287 0.8774 0.2523 0.061*
C22 0.3503 (3) 0.9713 (2) 0.1118 (2) 0.0390 (8)
C23 0.3431 (3) 0.8117 (3) 0.0361 (2) 0.0434 (9)
C24 0.4163 (4) 0.8472 (3) −0.0355 (2) 0.0621 (11)
H24A 0.3886 0.9129 −0.0520 0.093*
H24B 0.4067 0.8004 −0.0796 0.093*
H24C 0.5005 0.8509 −0.0206 0.093*
C25 0.2092 (3) 0.8168 (3) 0.0196 (3) 0.0718 (13)
H25A 0.1652 0.7986 0.0677 0.108*
H25B 0.1890 0.7708 −0.0235 0.108*
H25C 0.1877 0.8844 0.0038 0.108*
C26 0.3812 (4) 0.7062 (3) 0.0620 (2) 0.0649 (12)
H26A 0.4640 0.7075 0.0803 0.097*
H26B 0.3739 0.6609 0.0167 0.097*
H26C 0.3297 0.6835 0.1054 0.097*
C20a 0.3974 (8) 1.0152 (4) 0.3275 (3) 0.055 (2)
H20Aa 0.4842 1.0239 0.3347 0.065*
H20Ba 0.3624 0.9926 0.3784 0.065*
C20Ab 0.308 (3) 1.0062 (13) 0.3266 (11) 0.051 (7)
H20Cb 0.2206 0.9951 0.3266 0.061*
H20Db 0.3397 0.9920 0.3803 0.061*

  1. aOccupancy: 0.786 (16). bOccupancy: 0.214 (16).

Source of materials

4-Amino-12-bromine [2.2] paracyclophane was synthesized according to published procedures [6]. L-proline protected by tert-butyloxycarbonyl (10 mmol) and 1,3-dicyclohexylcarbodiimide (10 mmol) were dissolved in dry CH2Cl2 (50 mL) and stirred at room temperature for 5 min. Then racemic 4-amino-12-bromine[2.2]paracyclophane (10 mmol) in CH2Cl2 (20 mL) was added to the above solution and reacted 12 h at room temperature. The mixture was filtered under reduced pressure and the filtrate was rotatably dried to obtain the diastereoisomer products, which were separated by column chromatography with petroleum ether and ethyl acetate as mobile phase at room temperature. Colorless crystal of title compound was obtained by slow evaporation of chromatogram liquid.

Experimental details

The structure was solved by Direct Methods with the SHELX [3]. All H-atoms were positioned geometrically and refined using a riding model with d(C–H) = 0.93 Å, U iso = 1.2U eq (C) for aromatic, 0.97 Å, U iso = 1.2U eq (C) for CH2, 0.98 Å, U iso = 1.2U eq (C) for CH, 0.96 Å, U iso = 1.5U eq (C) for CH3 atoms and d(N–H) = 0.86 Å, U iso = 1.2U eq (N) for NH. A CH2 group of the 5-membered ring is disordered and treated with a split operation, with site occupancies of 0.786 for C20 and 0.214 for C20A. As a result, the H atoms on C19 and C21 were split automatically. The absolute structure was established by refinement of the Flack parameter (−0.007(5) from 1210 selected quotients) using Parsons’ method [7].

Comment

The planar chiral ligands are widely used in asymmetric catalysis. Because of the unique skeleton structure, easy to construct a planar chiral environment to achieve better stereoscopic control, [2.2]paracyclophane derivatives play an important role in this field. Among them, 4,12-disubstitution [2.2]paracyclophane is a typical intermediate for building planar chiral ligands. And many excellent catalysts based on 4,12-disubstitution [2.2]paracyclophane derivatives have been reported [8]. Growth and characterization of single crystal are very important for the chiral resolution, structure identification, structure-activity relationship and mechanism study of these ligands. We have luckily obtained the single crystal of the title compound in the course of the resolution of 4-amino-12-bromine [2.2] paracyclophane.

The structure of the title compound is illustrated in the figure, its absolute configuration of the [2.2] paracyclophane moiety is established as (Sp) by comparison with the known conguration of the l-proline moiety residues. The single crystal structure verifies that all bond lengths are in normal ranges. The dihedral angles of the two planes that across C4/C5/C7/C8 and C12/C13/C15/C16 is up to 2.75(9)° which is between the similar structures 4-bromo-12-camphanoyloxy[2.2]paracyclophane and 4-bromo-12-(t-butylsulfinyl)tricyclo-[2.2]paracyclophane [9, 10]. However, the side with substituents C4/C5 and C12/C13 is significantly closer to each other than the other side which is unusual to the similar structures [9, 10]. This may be the case due to the involvement of substituents in intermolecular and intramolecular interactions such as hydrogen or halogen bonds. The presence of hydrogen bonds [C21–H21⋯O1i symmetry code i: 1 − x, −1/2 + y, 1/2 − z] or potential weak interactions between bromine atom and acyl oxygen atom from another molecule [O1i⋯Br1 = 3.285 (7) symmetry code i: 1 − x, −1/2 + y, 1/2 − z], results in the formation of a chain structure along the (010) direction. The 1D structures are further connected by non-classical hydrogen bonds between C–H donors and the acyl oxygen atom [C15–H15⋯O1ii symmetry code ii: 1/2 + x, 5/2 − y, −z] forming a 3D structure.

Corresponding author: Sun Yanwen, School of Chemistry and Chemical Engineering, Hebei Normal University for Nationalities, Higher Education Park, Chengde 067000, P. R. China, E-mail:

Acknowledgements

We gratefully acknowledge support by Scientific Research Program Funded by Hebei Province Education Department (BJ2019205), the Science and Technology Research and Development Project of Chengde (No. 202109A115) and higher education teaching reform research project of Hebei province (2019GJJG515).

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

  2. Research funding: Scientific Research Program Funded by Hebei Province Education Department (BJ2019205), the Science and Technology Research and Development Project of Chengde (No. 202109A115) and Higher Education Teaching Reform Research Project of Hebei Province (2019-GJJG515).

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

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Received: 2022-09-16
Accepted: 2022-10-10
Published Online: 2022-10-24
Published in Print: 2022-12-16

© 2022 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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  60. The crystal structure of (E)-3′,6′-bis(diethylamino)-2-((5-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C39H45N5O3
  61. The crystal structure of 2-(4-methoxynaphthalen-1-yl)-4H-chromen-4-one, C20H14O3
  62. The crystal structure of trans-dichlorido-(ethylenediamine-κ 2 N,N′)-bis(triphenylphosphine-κ 1 P)ruthenium(II), C38H38Cl2N2P2Ru
  63. The double polymeric chain of catena-poly[(μ2-6-bromopyridine-3-carboxylato-κ2 O,O′) (6-bromopyridine-3-carboxylato-κ2 O,O′) (μ2-1,2-bis(4-pyridyl)ethylene-κ2 N:N′)cobalt(II)], C24H16CoBr2N4O4
  64. The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3
  65. The crystal structure of (Z)-2-(2,3-dimethoxybenzylidene)naphtho[1,2-b]furan-3(2H)-one, C21H16O4
  66. Crystal structure of 2-hydroxy-1-tosylindolin-3-yl- 2-naphthoate, C26H21N1S1O5
  67. The crystal structure of 1-methyl-N-(1-methyl-1H-imidazole-2-carbonyl)-1H-imidazole-2-carboxamide, C10H11N5O2
  68. The crystal structure of (E)-2-((5-bromo-2-hydroxybenzylidene)amino)-3′,6′-bis(ethylamino)-2′, 7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one, C33H31BrN4O3
  69. The crystal structure of dimethanol-5,15-diphenylporphyrin-21,23-diido-κ4 N,Nʹ,Nʺ,Nʹʺ-manganese(III) trans-dicyanido-bis(acetylacetonato-κ2O,Oʹ)ruthenium(III), C46H42N6O6RuMn
  70. Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3,5-dicarboxybenzoate), C28H36N4O12
  71. Bifurcated halogen bonds in the crystal structure of 2,2′-bi(1,8-naphthyridine)—1,4-diiodotetrafluorobenzene (1/1), C22H10F4I2N4
https://doi.org/10.1515/ncrs-2022-0458
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 1,5-bis(4-chlorophenyl)-3-(3-methylphenyl)pentane- 1,5-dione, C48H40Cl4O4
  4. Crystal structure of (bis(1,10-phenanthroline-κ 2 N,N′))-(3,5-dinitrosalicylato-κ 2 O,O′)nickel(II), C31H18N6NiO7
  5. Crystal structure of {N,N′-bis(4-fluoro-salicylaldehyde)-3,6-dioxa-1,8-diaminooctane-κ4 O,N,N′,O′}zinc(II), C20H20F2N2O4Zn
  6. [5-Bromo-2-(2-(dimethylamino)ethyliminomethyl)phenolato-κ3 N,N′,O]-isothiocyanato-nickel(II), C12H14BrN3NiOS
  7. Crystal structure of 9-bromo-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin- 2-amine, C18H15BrN4O
  8. The crystal structure of imidazolium nitrate, C3H5O3N3
  9. Crystal structure of diiodido-bis(6,6′-dimethoxy-2,2′-(ethane-1,2-diylbis(nitrilomethanylylidene)) diphenolato)tricadmium(II), C36H36Cd3I2N4O8
  10. Crystal structure of [diaqua-bis(2-((1H-tetrazol-1-yl)methyl)-5-carboxy-1H-imidazole-4-carboxylato-κ2 N,O) manganese(II)] dihydrate, C14H18MnN12O12
  11. Crystal structure of Diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-k4 O,O′,N,N′)]iron(II), C13H14FeN4O10
  12. Crystal structure of poly[dimethanol-κ1O-(µ2-(E)-2-((2-oxidobenzylidene)amino)acetato)-(µ3-(E)-2-((2-oxidobenzylidene)amino)acetato)dicadmium(II)], C20H22Cd2N2O8
  13. Crystal structure of N 2,N 6-bis(2-(((E)-quinolin-8-ylmethylene)amino)phenyl)pyridine-2,6-dicarboxamide, C39H27N7O2
  14. An I 6 2 − anion in the crystal structure of theophyllinium triiodide monohydrate, C7H11I3N4O3
  15. The crystal structure of poly[6,6′-oxybis(4-(pyridin-1-ium-1-yl)-1,3,5,2,4,6-trioxatriborinan-2-olate)], [B6O9](C5H5N)2
  16. The crystal structure of (carbonato κ2 O,O′)(2-oxopyridin-1(2H)-olato-κN)tris(trimethylphosphine)rhodium(III) water solvate, C15H33NO5P3Rh
  17. The crystal structure of dibromido-bis((RS)-2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile-κ1 N)zinc(II), C30H34Br2Cl2N8Zn
  18. Synthesis and crystal structure of 3-(((7-hydroxy-3-(4-hydroxy-3,5-dinitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)(nitroso)amino)propanoic acid, C19H14N4O11
  19. The crystal structure of 3-((4-chloro-N-(2-methoxyethyl)benzamido)methyl)phenyl methanesulfonate, C18H20ClNO5S
  20. Crystal structure of di([1,1′:3′,1″-terphenyl]-2′-yl)tellane, C36H26Te
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]-pyrimidine-3-carboxylato-κ2 N,O)zinc(II), C14H12N6O6Zn
  22. Crystal structure of N′,N‴-((1E,2E)-1,2-diphenylethane-1,2-diylidene)bis(4-methylbenzohydrazide) – water – methanol (1/1/1), C31H32N4O4
  23. Crystal structure of 3-((2,4-dichlorobenzyl)thio)-5-methyl-7-(trifluoromethyl)-[1,2,4]triazolo [4,3-c]pyrimidine, C14H9Cl2F3N4S
  24. Crystal structure of 3,5,6,7-tetramethoxy-3′,4′-methylenedioxy-flavone, C20H18O8
  25. Crystal structure of catena-poly[(5,5′-dimethyl-2,2′-bipyridine-κ 2 N,N′)-(μ 3-hydrogen-1,1′,1″-(1,3,5-triazine-2,4,6-triyl)tris(piperidine-4-carboxylato)- κ 5 O:O,O′:O″,O‴)-cadmium(II)], C33H40CdN8O6
  26. The crystal structure of 3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C9H17N3
  27. Crystal structure of [(1,4,7,10-tetraoxacyclododecane-κ 4 O,O′,O″, O‴)-tris(nitrato-κ 2 O,O′)gadolinium(III)], C8H16N3O13Gd
  28. The crystal structure of 2,2′-((pyridine-2,6-diylbis(methylene))bis(sulfanediyl))-bis(4,5-dihydro-1H-imidazol-3-ium) bromide, C13H19Br2N5S2
  29. Crystal structure of E-2-chloro-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)benzohydrazide, C16H14Cl2N2O2
  30. Crystal structure of 3-(adamantan-1-yl)-4-methyl-5-{[(4-nitrophenyl)methyl]sulfanyl}-4H-1,2,4-triazole, C20H24N4O2S
  31. The crystal structure of dimethanol-κ1O-(5,10,15,20-tetrakis(4-nitrophenyl)porphyrin-21,23-diido-κ4 O,O′,O″,O′″)manganese(III) trans-dicyanido-κ1C-bis(acetylacetonato-κ2 O,O′)ruthenium(III), C58H46N10O14RuMn
  32. The crystal structure of nitroxyl-κ N-{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl-κN 3)borato}nickel(II), C15H13BF9N7NiO
  33. The crystal structure of [(2,2′-bipyridine-κ2 N,N)-bis(6-phenylpyridine-2-carboxylato- κ2 N,O)nickel(II)] monohydrate, C34H26N4O5Ni
  34. The crystal structure of 5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione, C20H15F5N2O3
  35. The crystal structure of ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate, C14H12F3NO3
  36. [2,2′-{Ethane-1,2-diylbis[(azanylylidene)methanylylidene]}bis(3-bromo-2-hydroxyphenyl)]iron(III) nitrate, C20H12Br2CuN2O2
  37. The crystal structure of 1-(2-iodophenyl)-4-phenyl-1H-1,2,3-triazole, C14H10IN3
  38. Synthesis and crystal structure of 2-(2-oxo-2-(thiophen-2-yl)ethyl)-4H-chromen-4-one, C15H10O3S
  39. {6,6′-((1E,1′E)-((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-bromo-4-chlorophenolate)-κ4N,N′,O,O′}copper(II), C19H16Br2Cl2CuN2O2
  40. The crystal structure of N′-[bis(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide, C19H15N3O3
  41. Crystal structure of 2-chloro-6-formylphenolato-κ2O,O′-(6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-chlorophenolato)κ4 N,N,O,O′)cobalt(III), C26H22Cl3CoN2O4
  42. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylate-κ 2 N,O)-bis(μ2-6-phenylpyridine-2-carboxylate-κ 2 O:O′)-bis(μ2-6-phenylpyridine-2-carboxylate-κ 3N,O:O)tetralead(II) C48H32N4O8Pb2
  43. The crystal structure of 3,7-dihydroxy-9-methoxy-4a-methyl-4aH-benzo[c] chromene-2,6-dione —dichloromethane (1/1), C16H14Cl2O6
  44. The crystal structure of (Z)-6-(((5-chloro-2-hydroxyphenyl)amino)methylene)- 4-nitrocyclohexa, C13H9ClN2O4
  45. Crystal structure of dichlorido-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1 N)zinc(II), C60H68O4N12Cl10Zn
  46. The crystal structure of 4-(2-bromoethoxy)-2-hydroxybenzaldehyde, C9H9BrO3
  47. The crystal structure of 5-azido-1-methyl-4-nitroimidazole, C4H4O2N6
  48. Crystal structure of dibromido-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), C60H68O4N12Br2Cl8Zn
  49. Crystal structure of tetrasodium-bis(μ 2-oxido)-hexafluoro-didioxo-molybdenum(V), Na2(Mo2O4F6)
  50. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4- hydroxybenzohydrazide-water (1/1), C14H13Cl1N2O4
  51. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinolin-2-yl)methanimine, C20H19N3O
  52. The crystal structure of catena-poly[(1,10-phenanthroline-κ2 N,N′)-(μ3-2-hydroxybenzene-1,3-dicarboxylato-κ5 O,O′:O″,O‴:O‴)cadmium(II)], C20H12CdN2O5
  53. The crystal structure of 2,6-di-tert-butyl-4-(4-(methylthio)benzylidene)cyclohexa-2,5-dien-1-one, C22H28OS
  54. La3.65Mg30Sb1.07 as a disordered derivative of Th2Ni17-type structure
  55. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinoxalin-2-yl)methanimine, C19H18N4O
  56. The crystal structure of 2,2′-(1,2-phenylenebis(methylene))bis(1,3-dimethylisothiouronium) bromide, C14H24Br2N4S2
  57. Crystal structure of tetraaqua-bis[4-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N]zinc(II), C18H20ZnN6O8
  58. Crystal structure of bis(tricarbonyl)-{(S)-(tert-butoxycarbonyl)(1-methoxy-1-oxo-3-sulfido-k2 S:S′-propan-2-yl)amido-k2N:N′}diiron(I) (Fe—Fe), C15H15Fe2NO10S
  59. Crystal structure of (E)-3-((4-chlorophenyl)thio)-4-hydroxypent-3-en-2-one, C11H11ClO2S
  60. The crystal structure of (E)-3′,6′-bis(diethylamino)-2-((5-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C39H45N5O3
  61. The crystal structure of 2-(4-methoxynaphthalen-1-yl)-4H-chromen-4-one, C20H14O3
  62. The crystal structure of trans-dichlorido-(ethylenediamine-κ 2 N,N′)-bis(triphenylphosphine-κ 1 P)ruthenium(II), C38H38Cl2N2P2Ru
  63. The double polymeric chain of catena-poly[(μ2-6-bromopyridine-3-carboxylato-κ2 O,O′) (6-bromopyridine-3-carboxylato-κ2 O,O′) (μ2-1,2-bis(4-pyridyl)ethylene-κ2 N:N′)cobalt(II)], C24H16CoBr2N4O4
  64. The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3
  65. The crystal structure of (Z)-2-(2,3-dimethoxybenzylidene)naphtho[1,2-b]furan-3(2H)-one, C21H16O4
  66. Crystal structure of 2-hydroxy-1-tosylindolin-3-yl- 2-naphthoate, C26H21N1S1O5
  67. The crystal structure of 1-methyl-N-(1-methyl-1H-imidazole-2-carbonyl)-1H-imidazole-2-carboxamide, C10H11N5O2
  68. The crystal structure of (E)-2-((5-bromo-2-hydroxybenzylidene)amino)-3′,6′-bis(ethylamino)-2′, 7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one, C33H31BrN4O3
  69. The crystal structure of dimethanol-5,15-diphenylporphyrin-21,23-diido-κ4 N,Nʹ,Nʺ,Nʹʺ-manganese(III) trans-dicyanido-bis(acetylacetonato-κ2O,Oʹ)ruthenium(III), C46H42N6O6RuMn
  70. Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3,5-dicarboxybenzoate), C28H36N4O12
  71. Bifurcated halogen bonds in the crystal structure of 2,2′-bi(1,8-naphthyridine)—1,4-diiodotetrafluorobenzene (1/1), C22H10F4I2N4
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