Home Physical Sciences Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
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Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S

  • Mohammad M. Al-Sanea , Olivier Blacque , Ahmed A. B. Mohamed , Edward R. T. Tiekink ORCID logo and Ali A. El-Emam ORCID logo EMAIL logo
Published/Copyright: January 31, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 2

Abstract

C18H17BrF3N3S, triclinic, P 1 ‾ (no. 2), a = 8.6380(2) Å, b = 14.5082(3) Å, c = 14.8000(3) Å, α = 98.177(2)°, β = 97.015(2)°, γ = 91.111(2)°, V = 1820.89(7) Å3, Z = 4, R gt(F) = 0.0296, wR ref(F 2) = 0.0783, T = 160 K.

CCDC no.: 2221199

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 plate
Size: 0.22 × 0.03 × 0.02 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 4.48 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θ max, completeness: 74.5°, >99%
N(hkl)measured, N(hkl)unique, R int: 38,076, 7420, 0.026
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 6960
N(param)refined: 477
Programs: CrysAlisPRO [1], SHELX [2, 3], Olex2 [4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.02986 (3) 0.32258 (2) 0.12114 (2) 0.03529 (7)
S1 0.20919 (5) 0.13799 (3) 0.52076 (3) 0.02374 (10)
F1 1.31551 (16) 0.22694 (12) 0.78143 (10) 0.0506 (4)
F2 1.39456 (18) 0.19727 (13) 0.91713 (14) 0.0662 (5)
F3 1.25805 (19) 0.31559 (10) 0.89827 (11) 0.0516 (4)
N1 0.44623 (19) 0.19903 (12) 0.44082 (12) 0.0245 (3)
H1 0.531 (3) 0.2284 (19) 0.4534 (19) 0.036 (7)*
N2 0.51512 (18) 0.12134 (11) 0.56345 (11) 0.0217 (3)
N3 0.76185 (18) 0.09660 (11) 0.70631 (11) 0.0236 (3)
C1 0.1632 (2) 0.28321 (14) 0.21907 (13) 0.0253 (4)
C2 0.1534 (2) 0.19098 (15) 0.23319 (14) 0.0270 (4)
H2 0.083563 0.147744 0.193001 0.032*
C3 0.2469 (2) 0.16222 (14) 0.30690 (14) 0.0254 (4)
H3 0.242293 0.098967 0.316686 0.030*
C4 0.3467 (2) 0.22645 (13) 0.36599 (13) 0.0216 (4)
C5 0.3587 (2) 0.31805 (13) 0.34923 (14) 0.0239 (4)
H5 0.430063 0.361156 0.388483 0.029*
C6 0.2667 (2) 0.34690 (14) 0.27516 (14) 0.0251 (4)
H6 0.274896 0.409374 0.263372 0.030*
C7 0.3999 (2) 0.15322 (12) 0.50757 (13) 0.0204 (4)
C8 0.4848 (2) 0.07597 (14) 0.64187 (14) 0.0260 (4)
H8A 0.493807 0.007768 0.626455 0.031*
H8B 0.377357 0.088163 0.655959 0.031*
C9 0.6007 (2) 0.11258 (15) 0.72519 (14) 0.0277 (4)
H9A 0.587521 0.180182 0.742420 0.033*
H9B 0.579634 0.081014 0.777735 0.033*
C10 0.7940 (2) 0.14197 (14) 0.62798 (13) 0.0237 (4)
H10A 0.900683 0.127762 0.613530 0.028*
H10B 0.789288 0.210336 0.644413 0.028*
C11 0.6771 (2) 0.10914 (13) 0.54384 (13) 0.0227 (4)
H11A 0.696480 0.144702 0.493735 0.027*
H11B 0.691949 0.042463 0.522447 0.027*
C12 0.8746 (2) 0.11135 (13) 0.78500 (14) 0.0252 (4)
C13 1.0182 (2) 0.15724 (13) 0.78545 (14) 0.0251 (4)
H13 1.042415 0.180323 0.731690 0.030*
C14 1.1261 (2) 0.16924 (14) 0.86450 (15) 0.0277 (4)
C15 1.0961 (3) 0.13708 (17) 0.94423 (16) 0.0373 (5)
H15 1.171003 0.145448 0.997603 0.045*
C16 0.9527 (3) 0.0921 (2) 0.94383 (18) 0.0455 (6)
H16 0.928431 0.070452 0.998241 0.055*
C17 0.8449 (3) 0.07832 (17) 0.86598 (17) 0.0374 (5)
H17 0.748800 0.045849 0.867223 0.045*
C18 1.2730 (3) 0.22557 (16) 0.86574 (16) 0.0339 (5)
Br2 −0.44430 (3) 0.06290 (2) 0.10760 (2) 0.04414 (8)
S2 −0.28605 (5) 0.36486 (3) 0.52555 (3) 0.02317 (10)
F4 0.81934 (17) 0.34564 (12) 0.79008 (10) 0.0499 (4)
F5 0.90840 (19) 0.42944 (12) 0.91585 (15) 0.0702 (6)
F6 0.7446 (2) 0.31742 (13) 0.91454 (14) 0.0663 (5)
N4 −0.05632 (19) 0.27716 (11) 0.44524 (12) 0.0235 (3)
H4 0.030 (3) 0.2506 (18) 0.4569 (18) 0.033 (7)*
N5 0.02240 (18) 0.39313 (11) 0.56546 (11) 0.0217 (3)
N6 0.27815 (18) 0.46454 (11) 0.70017 (11) 0.0221 (3)
C19 −0.3261 (2) 0.12955 (14) 0.21486 (14) 0.0269 (4)
C20 −0.3463 (2) 0.22411 (14) 0.23598 (14) 0.0270 (4)
H20 −0.419724 0.254532 0.198283 0.032*
C21 −0.2585 (2) 0.27427 (14) 0.31277 (14) 0.0249 (4)
H21 −0.268984 0.339641 0.326756 0.030*
C22 −0.1551 (2) 0.22833 (13) 0.36913 (13) 0.0212 (4)
C23 −0.1372 (2) 0.13288 (13) 0.34686 (14) 0.0245 (4)
H23 −0.066301 0.101693 0.385320 0.029*
C24 −0.2220 (2) 0.08300 (14) 0.26898 (15) 0.0283 (4)
H24 −0.208802 0.018089 0.253200 0.034*
C25 −0.0975 (2) 0.34492 (12) 0.51099 (13) 0.0200 (4)
C26 −0.0018 (2) 0.46232 (13) 0.64427 (14) 0.0248 (4)
H26A −0.107314 0.452448 0.661682 0.030*
H26B 0.005411 0.525714 0.627319 0.030*
C27 0.1203 (2) 0.45378 (14) 0.72517 (13) 0.0246 (4)
H27A 0.105376 0.502209 0.777355 0.030*
H27B 0.107393 0.392068 0.745092 0.030*
C28 0.3026 (2) 0.39209 (13) 0.62448 (13) 0.0237 (4)
H28A 0.292659 0.329932 0.643910 0.028*
H28B 0.409020 0.399730 0.607522 0.028*
C29 0.1825 (2) 0.39919 (14) 0.54223 (13) 0.0231 (4)
H29A 0.199566 0.459187 0.519707 0.028*
H29B 0.196463 0.348320 0.492042 0.028*
C30 0.3984 (2) 0.48190 (13) 0.77514 (13) 0.0217 (4)
C31 0.5299 (2) 0.42774 (13) 0.78379 (13) 0.0234 (4)
H31 0.540025 0.375087 0.739046 0.028*
C32 0.6461 (2) 0.45088 (14) 0.85792 (14) 0.0246 (4)
C33 0.6372 (2) 0.52789 (14) 0.92368 (14) 0.0272 (4)
H33 0.718308 0.543501 0.973317 0.033*
C34 0.5063 (2) 0.58188 (14) 0.91513 (14) 0.0272 (4)
H34 0.497665 0.634978 0.959630 0.033*
C35 0.3884 (2) 0.55925 (13) 0.84271 (13) 0.0246 (4)
H35 0.299416 0.596584 0.838610 0.029*
C36 0.7791 (3) 0.38692 (15) 0.87015 (15) 0.0312 (4)

Source of material

4-Bromophenyl isothiocyanate (1.07 g, 0.005 mol) was added to 10 mL of an ethanolic solution of 1-[(3-trifluoromethyl)phenyl]piperazine (1.15 g, 0.005 mol), and the mixture was refluxed for 1 h. The crude product was precipitated upon cooling, followed by filtration, washing with water and drying. Subsequent crystallisation from aqueous ethanol afforded 2.11 g (95%) of (I) as colourless plates. Melting point (uncorrected): 441-443 K. 1H NMR (CDCl3, 500.13 MHz): δ 3.37 (Piperazinyl-H, 4H, t, J = 6.5 Hz), 4.04 (Piperazinyl-H, 4H, t, J = 6.5 Hz), 7.05-7.17 (Aromatic-H & NH, 5H, m), 7.27 (Aromatic-H, 1H, s), 7.39 (Aromatic-H, 1H, t, 1H, J = 10 Hz), 7.48 (Aromatic-H, 2H, d, J = 10 Hz). 13C NMR (CDCl3, 125.76 MHz): δ 43.15, 43.98 (Piperazinyl-C), 107.38, 111.84, 113.97, 118.09, 120.36, 126.79, 127.11, 127.53, 134.08, 145.65 (Aromatic-C), 125.11 (CF3), 178.50 (C=S). Analysis calculated for C18H17BrF3N3S: C, 48.66; H, 3.86; N, 9.46; S, 7.22%. Found: C, 46.50; H, 3.90; N, 9.44; S, 7.20%.

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–0.99 Å) and refined as riding with U iso(H) = 1.2U eq(C). The N-bound H atoms were located in a difference map and refined freely.

Comment

The investigation of the title compound (I) was performed within the framework of medicinal chemistry. Thus, the piperazine-1-carbothioamide residue of (I) has been identified as a core pharmacophore in anti-fungal [5], anti-bacterial [6, 7], anti-inflammatory [8] and neuroprotective agents [9]. Herein, description of the synthesis, crystallographic characterisation as well as analysis of the calculated Hirshfeld surface are provided.

The molecular structures of the two independent molecules comprising the asymmetric-unit of (I) are shown in the upper images of the figure (70% probability ellipsoids). The molecules exhibit very similar conformations. Thus, the central CN2S residue for the S1-containing molecule has a r.m.s. deviation of 0.0021 Å and forms dihedral angles of 58.87(7) and 30.03(9)° with the bromophenyl and trifluorophenyl rings, respectively; the dihedral angle between the substituted phenyl rings is 48.22(8)°. The equivalent values for the second independent molecule are close, at 0.0062 Å and 53.9(7), 29.08(9) and 27.54(9)°, respectively, indicating the molecular conformations differ primarily only in the relative dispositions of the pendant phenyl groups.

Within the CN2S chromophore, the C7–N1, N2 bond lengths are experimentally equivalent [1.361(3) & 1.347(2) Å] and significantly shorter, as expected, than the C4–N1 [1.425(2) Å], and C8–N2 [1.461(2) Å] and C11–N2 [1.472(2) Å] bond lengths. The equivalent values for the second independent molecule are 1.366(2), 1.349(2), 1.419(2), 1.465(2) and 1.470(2) Å, indicating a close match with the first independent molecule.

There are three closely related literature structures with a piperazine linked to a CN2S chromophore. Two of these have a phenyl group at the N3-position, and at the N1-position, an adamantan-1-yl group [10] or a fused, three-ring system [11]. The third precedent has a 2-trifluoromethylphenyl group at the N3-position and an ethyl group at the N1-position [12]. The key geometric parameters among the four structures are in close accord.

The anti-disposition of the thione–S and amide–H atoms facilitates the formation of amide–N–H···S(thione) hydrogen bonds [N1–H1···S2 i : H1···S2 i  = 2.53(3) Å, N1···S2 i  = 3.3055(18) Å with angle at H1 = 156(2)° and N4–H4···S1: H4···S1 = 2.48(3) Å, N4···S1 = 3.2835(17) Å with angle at N2 = 157(2)° for symmetry operation (i): 1 + x, y, z] within a zigzag chain of alternate independent molecules aligned along the a-axis, as illustrated in the lower view of the figure (non-participating H atoms have been removed for clarity). The independent molecules self-associate via methylene–C–H···S(thione) [C11–H11b···S1 ii : H11b···S1 ii  = 2.78 Å, C11···S1 ii  = 3.7583(19) Å with angle at H11b = 169° and C29–H29a···S2 iii : H29a···S2 iii  = 2.84 Å, C29···S2 iii  = 3.821(2) Å with angle at H29a = 172° for (ii): 1 − x, −y, 1 − z and (iii): −x, 1 − y, 1 − z] interactions within a supramolecular layer in the ab-plane. The layers stack along the c-axis with close, Br2···Br2 iv contacts between centrosymmetrically related molecules. Thus, Br2···Br2 iv  = 3.4541(4) Å with an angle at Br2 = 163.76(6)° for (iv): −1 − x, −y, −z; the sum of the van der Waals radii amounts to 3.70 Å [13].

An analysis of the calculated Hirshfeld surfaces was also conducted to comprehend further the molecular packing and to ascertain differences in the surface contacts exhibited by the independent molecules [14, 15]. The surface contacts for each independent molecule are dominated by contacts involving H, i.e. H···H 87.7% for the S1-containing molecule [87.3% for the S2-containing molecule]. The major contributors to the surface contacts are H···H 29.9% [27.6%], C···H/H···C 17.6% [18.1%], F···H/H···F 16.1% [19.5%], S···H/H···S 10.9% [11.2%], Br···H/H···Br 10.0% [8.3%] and N···H/H···N 3.2% [2.6%]. The differential in the F···H/H···F contacts is the greatest distingushing feature between the molecules. Another notable difference relates to Br···Br contacts which are 0.0 and 1.3% for the independent molecules, respectively. There are Br···F/F···Br contacts worth highlighting, namely 4.6 and 3.4%, respectively, as well as F···F contacts of 1.4 and 2.3%, respectively.

Corresponding author: Ali A. El-Emam, Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt, E-mail:

Funding source: Deanship of Scientific Research at Jouf University

Award Identifier / Grant number: DSR-2021-01-03115

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

  2. Research funding: This work was funded by the Deanship of Scientific Research at Jouf University under grant No. DSR-2021-01-03115.

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

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Received: 2022-11-26
Accepted: 2023-01-03
Published Online: 2023-01-31
Published in Print: 2023-04-25

© 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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  24. Synthesis and crystal structure of 8-bromo-3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one, C13H7BrN2O3
  25. Crystal structure of E-7-fluoro-2-(4-methoxy-3-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  26. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-((3,5-dimethylphenyl)carbamoyl)-nicotinamide, C30H28Cl2N6O4
  27. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
  28. Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
  29. Crystal structure of pentacarbonyl-(μ2-ethane-1,2-dithiolato-κ4S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1P)diiron (Fe–Fe), C26H21Fe2O5PS2
  30. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)- 5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2
  31. Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ3 O,O′,O″]nickel(II), C9H11BrNiO8
  32. The crystal structure of 4,4′-dichloro-3,5′-diphenyl-1′H-1,3′- bipyrazole, C18H12Cl2N4
  33. The crystal structure of bis(1H-pyrazole-carboxamidine-κN,N′)bis(nitrato-κO)-copper(II), C8H12CuN10O6
  34. Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene, C15H11BrO
  35. Crystal structure of (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
  36. Crystal structure of niobium trigallide, NbGa3
  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
https://doi.org/10.1515/ncrs-2022-0544
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of methyl 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl) thio)phenoxy)methyl)benzoate, C17H13ClF4O3S
  4. The crystal structure of 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate, C10H14O6
  5. Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
  6. Crystal structure of 1-(3-bromopropyl)-2-((4-chlorophenoxy)methyl)-4-methyl-1H-benzo[d]imidazole, C18H18BrClN2O
  7. Crystal structure of 2-methoxy-6-[(2-morpholin-4-yl-phenylamino)-methylene]-4-nitro-cyclohexa-2,4-dienone, C18H19N3O5
  8. The crystal structure of 2-(7-(2,3-dimethoxyphenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-5-yl)-3-methoxyphenol, C20H18N4O4
  9. The crystal structure of 3-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinyl)ethylidene)chroman-2,4-dione dihydrate, C20H22N2O8
  10. Crystal structure of 3,5,7-trimethoxy-3′,4′-methylenedioxy-flavone, C19H16O7
  11. The crystal structure of strictic acid, C20H26O3
  12. Crystal structure of 1,1′-(pyrazine-1,4-diyl)-bis(propan-2-one), C10H14N2O2
  13. The crystal structure of 1-(adamantan-1-yl)-3-(4-chlorophenyl)urea, C17H21ClN2O
  14. The crystal structure of (2R,6′R)-2′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-2′-ene-3,4′-dione, C16H14Cl2O5
  15. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-3-((4-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]-phenanthren-17-yl)ethan-1-one, C28H41NO2
  16. Crystal structure of N-2,6-difluorobenzoyl-N′-[1-(3-chloro-4-methyl-phenyl)-4-cyano-1H-pyrazol-5-carbamoyl]urea, C19H12ClF2N5O2
  17. Crystal structure of (−)-β-D-19-glucopiranosyl-9,15-dihydroxy kaurenoate, C26H40O9
  18. Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4
  19. Crystal structure of S-(benzo[d]thiazol-2-yl)-N-(tert-butyl)thiohydroxylamine, C11H14N2S2
  20. Crystal structure of poly[di-µ2-aqua-aqua-nitrato-κ2O,O′-(µ3-2-nitroisophthalato-κ4O,O′:O″:O′″)barium(II)natrium(II)] monohydrate, C8H11BaN2NaO13
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2 N,O)-cobalt(II) dihydrate, C14H16N6O8Co
  22. Crystal structure of (S,E)-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-4-yl)-2,3- dihydroquinazolin-4(1H)-one monohydrate, C19H15N5O⋅H2O
  23. Synthesis and crystal structure of 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate monohydrate, C22H24N2O12S
  24. Synthesis and crystal structure of 8-bromo-3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one, C13H7BrN2O3
  25. Crystal structure of E-7-fluoro-2-(4-methoxy-3-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  26. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-((3,5-dimethylphenyl)carbamoyl)-nicotinamide, C30H28Cl2N6O4
  27. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
  28. Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
  29. Crystal structure of pentacarbonyl-(μ2-ethane-1,2-dithiolato-κ4S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1P)diiron (Fe–Fe), C26H21Fe2O5PS2
  30. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)- 5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2
  31. Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ3 O,O′,O″]nickel(II), C9H11BrNiO8
  32. The crystal structure of 4,4′-dichloro-3,5′-diphenyl-1′H-1,3′- bipyrazole, C18H12Cl2N4
  33. The crystal structure of bis(1H-pyrazole-carboxamidine-κN,N′)bis(nitrato-κO)-copper(II), C8H12CuN10O6
  34. Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene, C15H11BrO
  35. Crystal structure of (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
  36. Crystal structure of niobium trigallide, NbGa3
  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
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