Home Physical Sciences Crystal structure of (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, C16H14N2OS
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Crystal structure of (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, C16H14N2OS

  • Pule Seboletswe , Sizwe J. Zamisa ORCID logo , Gobind Kumar and Parvesh Singh EMAIL logo
Published/Copyright: February 28, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 3

Abstract

C16H14N2OS, monoclinic, P21/n (no. 14), a = 13.8369(4) Å, b = 15.8967(4) Å, c = 13.8600(4) Å, β = 109.983(1)°, V = 2865.11(14) Å3, Z = 8, R gt(F) = 0.0439, wR ref(F 2) = 0.1091, T = 296.15 K.

CCDC no.: 2322788

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 block
Size: 0.21 × 0.18 × 0.12 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.22 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.5°, 99 %
N(hkl)measured, N(hkl)unique, R int: 43,056, 6440, 0.029
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 5007
N(param) refined: 411
Programs: Bruker [1], Olex2 [2], Shelx [3], Olex2 [4]
Table 2:

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

Atom x y z U iso*/U eq
S1 0.80113 (11) 0.48262 (8) 0.52504 (12) 0.0746 (5)
O1 0.59821 (13) 0.60062 (10) 0.60184 (16) 0.0893 (6)
N1 0.73209 (13) 0.71535 (9) 0.57983 (12) 0.0505 (4)
N2 0.74721 (12) 0.63002 (9) 0.57233 (12) 0.0502 (4)
C1 0.85699 (19) 0.91160 (14) 0.56051 (18) 0.0721 (6)
H1 0.91369 (19) 0.89048 (14) 0.54690 (18) 0.0865 (8)*
C2 0.8448 (2) 0.99829 (16) 0.5677 (2) 0.0886 (8)
H2 0.8940 (2) 1.03494 (16) 0.5600 (2) 0.1064 (10)*
C3 0.7604 (3) 1.02951 (15) 0.5861 (2) 0.0928 (9)
H3 0.7521 (3) 1.08731 (15) 0.5900 (2) 0.1114 (10)*
C4 0.6885 (3) 0.97586 (15) 0.5985 (2) 0.0913 (8)
H4 0.6313 (3) 0.99744 (15) 0.6109 (2) 0.1095 (10)*
C5 0.69976 (19) 0.89009 (13) 0.59293 (18) 0.0680 (6)
H5 0.65059 (19) 0.85410 (13) 0.60205 (18) 0.0816 (7)*
C6 0.78443 (16) 0.85726 (12) 0.57371 (14) 0.0521 (5)
C7 0.79769 (16) 0.76613 (12) 0.56561 (14) 0.0518 (5)
H7 0.85358 (16) 0.74544 (12) 0.55020 (14) 0.0621 (5)*
C8 0.67520 (18) 0.57766 (13) 0.58712 (18) 0.0620 (5)
C9 0.70427 (19) 0.48644 (13) 0.5843 (2) 0.0711 (6)
H9a 0.64470 (19) 0.45370 (13) 0.5449 (2) 0.0853 (8)*
H9b 0.73087 (19) 0.46369 (13) 0.6533 (2) 0.0853 (8)*
C10 0.83518 (15) 0.59357 (11) 0.55153 (14) 0.0493 (4)
H10 0.84076 (15) 0.61969 (11) 0.48961 (14) 0.0592 (5)*
C11 0.93671 (14) 0.60321 (10) 0.63844 (14) 0.0458 (4)
C12 1.02737 (16) 0.60309 (12) 0.61672 (16) 0.0546 (5)
H12 1.02459 (16) 0.60108 (12) 0.54876 (16) 0.0655 (6)*
C13 1.12151 (17) 0.60589 (13) 0.69432 (19) 0.0658 (6)
H13 1.18173 (17) 0.60487 (13) 0.67868 (19) 0.0789 (7)*
C14 1.1263 (2) 0.61021 (14) 0.7951 (2) 0.0761 (7)
H14 1.1897 (2) 0.61224 (14) 0.8477 (2) 0.0913 (8)*
C15 1.0364 (2) 0.61152 (16) 0.81768 (17) 0.0758 (7)
H15 1.0394 (2) 0.61480 (16) 0.88566 (17) 0.0910 (8)*
C16 0.94206 (18) 0.60798 (13) 0.73990 (16) 0.0624 (5)
H16 0.88194 (18) 0.60882 (13) 0.75571 (16) 0.0749 (6)*
S2 0.47471 (14) 0.87662 (8) 0.67313 (12) 0.0869 (6)
O2 0.39559 (15) 0.78070 (11) 0.88800 (13) 0.0852 (5)
N3 0.40935 (13) 0.65434 (9) 0.76625 (12) 0.0512 (4)
N4 0.42559 (13) 0.73714 (9) 0.74434 (12) 0.0508 (4)
C17 0.36990 (18) 0.48535 (13) 0.80700 (18) 0.0647 (6)
H17 0.35290 (18) 0.52688 (13) 0.84569 (18) 0.0776 (7)*
C18 0.3519 (2) 0.40260 (15) 0.8223 (2) 0.0884 (8)
H18 0.3230 (2) 0.38827 (15) 0.8715 (2) 0.1060 (10)*
C19 0.3762 (2) 0.34048 (15) 0.7655 (2) 0.0934 (9)
H19 0.3622 (2) 0.28452 (15) 0.7751 (2) 0.1120 (10)*
C20 0.4213 (2) 0.36117 (15) 0.6944 (2) 0.0854 (8)
H20 0.4391 (2) 0.31918 (15) 0.6568 (2) 0.1025 (9)*
C21 0.44020 (18) 0.44434 (13) 0.67901 (17) 0.0661 (6)
H21 0.47118 (18) 0.45824 (13) 0.63125 (17) 0.0794 (7)*
C22 0.41333 (15) 0.50752 (11) 0.73417 (15) 0.0516 (4)
C23 0.43125 (15) 0.59615 (11) 0.71380 (14) 0.0495 (4)
H23 0.45840 (15) 0.60956 (11) 0.66292 (14) 0.0594 (5)*
C24 0.41574 (16) 0.79630 (13) 0.81165 (16) 0.0559 (5)
C25 0.4356 (2) 0.88308 (13) 0.78137 (19) 0.0707 (6)
H25a 0.4890 (2) 0.90979 (13) 0.83772 (19) 0.0848 (7)*
H25b 0.3736 (2) 0.91672 (13) 0.76524 (19) 0.0848 (7)*
C26 0.45345 (15) 0.76256 (11) 0.65598 (14) 0.0466 (4)
H26 0.51791 (15) 0.73500 (11) 0.65947 (14) 0.0559 (5)*
C27 0.37313 (14) 0.74560 (10) 0.55294 (14) 0.0461 (4)
C28 0.40457 (19) 0.73730 (13) 0.46840 (15) 0.0616 (5)
H28 0.47430 (19) 0.73688 (13) 0.47728 (15) 0.0739 (6)*
C29 0.3324 (2) 0.72966 (15) 0.37109 (18) 0.0839 (7)
H29 0.3539 (2) 0.72466 (15) 0.31467 (18) 0.1007 (8)*
C30 0.2304 (3) 0.72940 (16) 0.3572 (2) 0.0958 (9)
H30 0.1824 (3) 0.72499 (16) 0.2914 (2) 0.1150 (11)*
C31 0.1980 (2) 0.73564 (15) 0.4404 (2) 0.0857 (8)
H31 0.1281 (2) 0.73437 (15) 0.4308 (2) 0.1028 (10)*
C32 0.26924 (16) 0.74381 (12) 0.53869 (18) 0.0617 (5)
H32 0.24719 (16) 0.74807 (12) 0.59481 (18) 0.0740 (6)*

1 Source of material

All reagents were purchased from Merck and used as obtained. The target compound was synthesized in two synthetic steps where the intermediate (1E,2E)-1,2-dibenzylidenehydrazine was obtained according to Brown with slight modification [5]. In the first step, benzaldehyde (19.6 mmol) and acetic acid (0.5 mL) were added to a round bottom flask containing 10 mL of absolute ethanol. To this mixture, 2 mol equivalence of hydrazine monohydrate was added dropwise and stirred at room temperature for 3 h. Thereafter, the precipitate was filtered and dried under vacuum. To synthesize (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, a procedure by Ravichandran [6] was employed with slight modification. A mixture of (1E,2E)-1,2-dibenzylidenehydrazine (1 mmol), thioglycolic acid (1 mmol) and a catalytic amount of ZnCl2 was refluxed at 100 °C overnight. After the completion of the reaction, as monitored by TLC, the solvent was removed under reduced pressure and the remaining residue was dissolved in ethyl acetate. The organic layer was then successively washed with water, 10 % NaHCO3 and brine solution. Subsequently, the organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the crude product. Slow evaporation of an ethanolic solution of the crude afforded colourless block crystals of the target compound. The crystals were collected by vacuum filtration and dried in vacuo. Yield = 67 %, 1 H NMR (400 MHz, DMSO‑d 6) δ (ppm): 8.26 (s, 1H, N=CH), 7.63 (d, 2H, Ar–H) 7.46–7.36 (m, 8H, Ar–H), 6.56 (s, 1H, thiazolidine-4-one-CH), 4.07 (d, J = 16.08 Hz, 1H, thiazolidine-4-one-CH2), 4.03 (d, J = 16.06 Hz, 1H, thiazolidine-4-one-CH2). 13 C NMR (151 MHz, DMSO‑d 6) δ (ppm): 168.08, 151.11, 140.07, 134.10, 131.18, 129.51, 129.33, 128.95, 127.77, 126,47, 60.90, 30.52.

2 Experimental details

Using Olex2 [2], the structure was solved with the Shelxt [3] structure solution program using intrinsic phasing and refined with the olex2.refine [4] refinement package.

3 Comment

Thiazolidinones are widely recognized for their remarkable biological properties, including anticancer [7] and antidiabetic effects [8, 9]. The electron-rich thiazole component of the pharmacophore makes it an ideal ligand for binding to enzymes and receptors [10]. As a result, medicinal chemists find thiazolidinones to be an intriguing subject of study [11]. In this work, we report a crystal structure of a novel thiazolidinone derivative.

The crystal structure of the title compound consists of two symmetrically independent molecules in the asymmetric unit. Each molecular unit has a thiazolidinone core with benzylideneamino and phenyl moieties bonded to the alpha nitrogen (N2 and N4) and beta carbon (C10 and C26) atoms, respectively. Despite the thiazolidinone core having two sp 3 hybridized carbons, the five-membered heterocycle is almost planar with N2–C8–C9–S1–C10 and N4–C24–C25–S2–C26 root mean squared deviation (RMSD) values of 0.111 and 0.030 Å, respectively. On one hand, the phenyl moiety is almost orthogonal with respect to the thiazolidinone core (dihedral angle = 98.42–100.43°) which is similar to the previously reported 3-anilino-5-methyl-2-phenyl-1,3-thiazolidin-4-one and 3-anilino-5-methyl-2-(4-methylphenyl)-1,3-thiazolidin-4-one derivatives [12]. On the other hand, the benzylideneamino group is relatively coplanar with the thiazolidinone core (dihedral angle = 6.87(7)–10.23(8)°) which is different from other substituted thiazolidinone derivatives [13, 14]. Intermolecular C23–H23⋯O1 (C23⋯O1 = 3.194(2) Å; C23–H23⋯O1 = 148°; symmetry code: x, y, z) and C7–H7⋯O2 (C7⋯O2 = 3.275(3) Å; C7–H7⋯O2 = 136°; symmetry code: 1/2 + x, 3/2 − y, −1/2 − z) hydrogen bonding patterns were observed in the crystal packing of the title compound. These C–H⋯O interactions join neighbouring molecules to form a chain structure that extends diagonally with respect to the crystallographic ac plane.

Corresponding author: Parvesh Singh, University of KwaZulu-Natal, School of Chemistry and Physics, Private Bag X54001, Westville Campus, Westville, 4000 Durban, South Africa, E-mail:

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

  2. Research funding: National Research Foundation (South Africa) for a Competitive grant for rated researchers (Grant Number: SRUG2204092857).

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

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Received: 2023-11-22
Accepted: 2023-12-31
Published Online: 2024-02-28
Published in Print: 2024-06-25

© 2023 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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  48. The crystal structure of (Z)-4-ethyl-2-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3,5-dimethyl-2H-pyrrol-1-ium 2,2'-spirobi[naphtho[1,8-de][1,3,2]dioxaborinin]-2-uide, C37H37BN2O4
  49. Crystal structure of bis(methylammonium) hexadecaselenidopalladate(II), (CH3NH3)2PdSe16
  50. The crystal structure of (2-diphenylphosphanylphenyl) 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate, C31H26NO4P
  51. Crystal structure of (E)-6-(4-ethylpiperazin-1-yl)-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C23H25FN2O
  52. The structure of RUB-56, (C6H16N)8 [Si32O64(OH)8]·32 H2O, a hydrous layer silicate (2D-zeolite) that contains microporous levyne-type silicate layers
  53. Crystal structure of 4-amino-3,5-dibromobenzonitrile, C7H4Br2N2
  54. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-acetoxybenzoate, C21H18O4
  55. Single-crystal structure determination of Tm3B12O19(OH)7
  56. Crystal structure determination of NdB3.6O7
  57. The crystal structure of NdB6O8(OH)5·H3BO3
  58. Crystal structure of 2-(5-ethylpyridin-2-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H25NO3
  59. Crystal structure of N-(1-(3,4-dimethoxyphenyl)-2-methylpropyl)aniline, C18H23NO2
  60. Crystal structure of Ba6Cd12Mn4SiF48
  61. Synthesis and crystal structure of 5-fluoro-1-methyl-2-oxo-3-(2-oxochroman-4-yl)indolin-3-yl acetate, C20H16FNO5
  62. The crystal structure of 6-methacryloylbenzo[d][1,3]dioxol-5-yl 4-nitrobenzenesulfonate, C17H13NO8S
  63. Crystal structure of ethyl 2-(3-benzyl-4-oxo-3,4-dihydrophthalazin-1-yl)- 2,2-difluoroacetate, C19H16F2N2O3
  64. The crystal structure of tetrakis(μ 2-(1H-benzimidazole-2-methoxo-κ2 N,O:O:O)-(n-butanol-κO)-chlorido)-tetranickel(II), C48H68Cl4N8O8Ni4
  65. Synthesis and crystal structure of trans-tetraaqua-bis((1-((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carbonyl)oxy-κO)zinc(II)hexahydrate, C46H64N2O28S2Zn
  66. The crystal structure of 1-(4-carboxybutyl)-3-methyl-1H-imidazol-3-ium hexafluoridophosphate, C9H15F6N2O2P
  67. Crystal structure of 1-(4-chlorophenyl)-4-(2-furoyl)-3-phenyl-1H-pyrazol-5-ol, C20H13ClN2O3
  68. Crystal structure of dimethyl (R)-2-(3-(1-phenylethyl)thioureido)-[1,1′-biphenyl]-4,4′-dicarboxylate, C25H24N2O4S
  69. The crystal structure of 1-(3-carboxypropyl)-1H-imidazole-3-oxide, C7H10N2O3
  70. Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
  71. Crystal structure of methyl-1-(p-tolyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C20H20N2O2
  72. The crystal structure of 1-(1-adamantan-1-yl)ethyl-3-(3-methoxyphenyl)thiourea, C20H28N2OS
  73. The crystal structure of N,N′-carbonylbis(2,6-difluorobenzamide), C15H8F4N2O3
https://doi.org/10.1515/ncrs-2023-0518
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of tris((Z)-2-hydroxy-N-((E)-pyridin-2-ylmethylene)benzohydrazonato-k2O,N)europium(III), C39H30N9O6Eu
  4. Crystal structure of (E)-3-(benzylideneamino)-2-phenylthiazolidin-4-one, C16H14N2OS
  5. The crystal structure of (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H15FN2O
  6. Crystal structure of (6-chloropyridin-3-yl)methyl 2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  7. Crystal structure of methyl 3-methoxy-4-(2-methoxy-2-oxoethoxy)benzoate, C12H14O6
  8. The crystal structure of bis[(4-methoxyphenyl)(picolinoyl)amido-κ2 N:N′]copper(II), C26H22CuN4O4
  9. The crystal structure of poly[di(μ2-aqua)-diaqua-bis(3-aminopyridine-4-carboxylate-κ2 O: O′)-tetra(μ2-3-aminopyridine-4-carboxylate-κ2 O: O′)-dineodymium(III), [Nd2(C6H5N2O2)6(H2O)4] n
  10. The crystal structure of t-butyl 7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate, C28H34FNO4
  11. Crystal structure of catena-poly[(benzylamine-κ1 N)-(sorbato-κ1 O)-(μ2-sorbato-κ2 O,O′)-copper(II), C19H23CuNO4
  12. Crystal structure of (4-(2-chlorophenyl)-1H-pyrrol-3-yl)(ferrocenyl) methanone, C21H16ClFeNO
  13. The crystal structure of N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3-(2-methylphenyl)-2-sulfanylprop-2-enamide hydrate, C19H17BrN2O2S2
  14. The crystal structure of N′-{5-[2-(2,6-dimethylphenoxy) acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide hydrate
  15. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C26H24O3
  16. Crystal structure of naphthalen-1-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C25H22O3
  17. Crystal structure of poly[diaqua- (μ4-5-(1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ5N:O,O’:O’’:O’’’)calcium(II), C10H9CaN3O6
  18. Crystal structure of (E)-N′-(4-((E)-3-(dimethylamino)acryloyl)-3-hydroxyphenyl)-N, N-dimethylformimidamide, C14H19N3O2
  19. Crystal structure of (E)-3-(dimethylamino)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, C13H17NO4
  20. Crystal structure of (2-chloropyridin-3-yl)methyl-2-(6-methoxynaphthalen-2-yl)propanoate, C20H18ClNO3
  21. The crystal structure of diethyl 4-(3,4-dimethylphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C21H27NO4
  22. Crystal structure of (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-17-((4-(2-phenylpropyl)phenyl)ethynyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H42O2
  23. Synthesis and crystal structure of 4-(4-cyclopropylnaphthalen-1-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, C15H13N3S
  24. Crystal structure of catena-poly[aqua-(2,6-di-(2-pyridyl)-pyridine-κ3 N,N′, N″)(μ2-1,4-naphthalene dicarboxylato-κ2 O,O′)nickel(II)], C27H19NiN3O5
  25. Crystal structure of 3-(diphenylphosphoryl)-3-hydroxy-1-phenylpropan-1-one, C21H19O3P
  26. The crystal structure of R,S-{N-[(2-oxidonaphthalen-1-yl)methylidene]phenylglycinato}divinylsilicon, C23H19NO3Si
  27. The crystal structure of 1,2,4-tris(bromomethyl)benzene, C9H9Br3
  28. Crystal structure of chlorido-[4-(pyridin-2-yl)benzaldehyde-κ2 N,C]-(diethylamine-κ1 N)platinum(II), C16H18ClN2OPt
  29. Crystal structure of 3-(methoxycarbonyl)-1-(4-methoxyphenyl)-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indol-2-ium chloride hydrate, C40H48Cl2N4O9
  30. The crystal structure of 1-(2-chlorobenzyl)-3-(3-chlorophenyl)urea, C14H12Cl2N2O
  31. Hydrothermal synthesis and crystal structure of aqua-tris(4-acetamidobenzoato-κ2 O,O′)-(1,10-phenanthroline-κ2 N,N′)terbium(III) hydrate C39H36N5O11Tb
  32. The crystal structure of zwitterionic 3-aminoisonicotinic acid, C6H6N2O2
  33. The crystal structure of bis{[monoaqua-μ2-4-[(pyridine-4-carbonyl)-amino]-phthalato-κ3 N:O,O′-(2,2′-bipyridine κ2 N,N′)copper(II)]}decahydrate, C48H56N8O22Cu2
  34. Crystal structure of poly[μ10-4,4′-methylene-bis(oxy)benzoatodipotassium], C15H10K2O6
  35. The crystal structure of catena-poly[[tetraaqua[(μ2-1,4-di(4-methyl-1-imidazolyl)benzene] cobalt(II)]bis(formate)], C16H24CoN4O8
  36. The crystal structure of (E)-2-chloro-5-((2-(nitromethylene)imidazolidin-1-yl)methyl)pyridine, C10H11ClN4O2
  37. The crystal structure of (E)-1-(((2-amino-4,5-dimethylphenyl)iminio)methyl)naphthalen-2-olate, C19H18N2O
  38. Crystal structure of N-(acridin-9-yl)-2-(4-methylpiperidin-1-yl) acetamide monohydrate, C21H25N3O2
  39. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2 O,O′)-zinc(II), C14H20Cl2N4O4Zn
  40. The crystal structure of 2,8-diethyl-1,3,7,9-tetramethyl-4λ4,5λ4-spiro[dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine-5,2′-naphtho[1,8-de][1,3,2]dioxaborinine], C25H29BN2O2
  41. The crystal structure of 5-tert-butyl-2-(5-tert-butyl-3-iodo-benzofuran-2-yl)-3-iodobenzofuran, C24H24I2O2
  42. Synthesis and crystal structure of methyl 2-{[4-(4-cyclopropyl-1-naphthyl)-4H-1,2,4-triazole-3-yl]thio} acetate, C18H17N3O2S
  43. The crystal structure of n-propylammonium bis(2,3-dimethylbutane-2,3-diolato)borate-boric acid (1/1), [C3H10N][C12H24BO4]·B(OH)3
  44. Crystal structure of methyl 1-(2-bromophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C19H17BrN2O2
  45. Crystal structure of (4-bromobenzyl)triphenylphosphonium bromide ethanol solvate, C52H48Br4OP2
  46. The crystal structure of unsymmetrical BOPHY C26H27BN4
  47. The crystal structure of Tb3B5O11(OH)2
  48. The crystal structure of (Z)-4-ethyl-2-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3,5-dimethyl-2H-pyrrol-1-ium 2,2'-spirobi[naphtho[1,8-de][1,3,2]dioxaborinin]-2-uide, C37H37BN2O4
  49. Crystal structure of bis(methylammonium) hexadecaselenidopalladate(II), (CH3NH3)2PdSe16
  50. The crystal structure of (2-diphenylphosphanylphenyl) 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate, C31H26NO4P
  51. Crystal structure of (E)-6-(4-ethylpiperazin-1-yl)-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C23H25FN2O
  52. The structure of RUB-56, (C6H16N)8 [Si32O64(OH)8]·32 H2O, a hydrous layer silicate (2D-zeolite) that contains microporous levyne-type silicate layers
  53. Crystal structure of 4-amino-3,5-dibromobenzonitrile, C7H4Br2N2
  54. Crystal structure of 2-(naphthalen-1-yl)ethyl 2-acetoxybenzoate, C21H18O4
  55. Single-crystal structure determination of Tm3B12O19(OH)7
  56. Crystal structure determination of NdB3.6O7
  57. The crystal structure of NdB6O8(OH)5·H3BO3
  58. Crystal structure of 2-(5-ethylpyridin-2-yl)ethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H25NO3
  59. Crystal structure of N-(1-(3,4-dimethoxyphenyl)-2-methylpropyl)aniline, C18H23NO2
  60. Crystal structure of Ba6Cd12Mn4SiF48
  61. Synthesis and crystal structure of 5-fluoro-1-methyl-2-oxo-3-(2-oxochroman-4-yl)indolin-3-yl acetate, C20H16FNO5
  62. The crystal structure of 6-methacryloylbenzo[d][1,3]dioxol-5-yl 4-nitrobenzenesulfonate, C17H13NO8S
  63. Crystal structure of ethyl 2-(3-benzyl-4-oxo-3,4-dihydrophthalazin-1-yl)- 2,2-difluoroacetate, C19H16F2N2O3
  64. The crystal structure of tetrakis(μ 2-(1H-benzimidazole-2-methoxo-κ2 N,O:O:O)-(n-butanol-κO)-chlorido)-tetranickel(II), C48H68Cl4N8O8Ni4
  65. Synthesis and crystal structure of trans-tetraaqua-bis((1-((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carbonyl)oxy-κO)zinc(II)hexahydrate, C46H64N2O28S2Zn
  66. The crystal structure of 1-(4-carboxybutyl)-3-methyl-1H-imidazol-3-ium hexafluoridophosphate, C9H15F6N2O2P
  67. Crystal structure of 1-(4-chlorophenyl)-4-(2-furoyl)-3-phenyl-1H-pyrazol-5-ol, C20H13ClN2O3
  68. Crystal structure of dimethyl (R)-2-(3-(1-phenylethyl)thioureido)-[1,1′-biphenyl]-4,4′-dicarboxylate, C25H24N2O4S
  69. The crystal structure of 1-(3-carboxypropyl)-1H-imidazole-3-oxide, C7H10N2O3
  70. Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
  71. Crystal structure of methyl-1-(p-tolyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C20H20N2O2
  72. The crystal structure of 1-(1-adamantan-1-yl)ethyl-3-(3-methoxyphenyl)thiourea, C20H28N2OS
  73. The crystal structure of N,N′-carbonylbis(2,6-difluorobenzamide), C15H8F4N2O3
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