Home Physical Sciences Crystal structure of the co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-chlorobenzoic acid (2/1), C35H25ClO10S4
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Crystal structure of the co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-chlorobenzoic acid (2/1), C35H25ClO10S4

  • Sang Loon Tan and Edward R.T. Tiekink EMAIL logo
Published/Copyright: February 28, 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

C35H25ClO10S4, triclinic, P1̄ (no. 2), a = 7.9798(2) Å, b = 10.2392(3) Å, c = 20.6956(4) Å, α = 103.632(2)°, β = 96.082(2)°, γ = 96.053(2)°, V = 1619.13(7) Å3, Z = 2, Rgt(F) = 0.0493, wRref(F2) = 0.1413, T = 100(2) K.

CCDC no.: 1890703

The molecular structure is shown in the figure. Tables 1 and 2, respectively, contain details on crystal characteristics and measurement conditions, and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless prism
Size:0.09 × 0.07 × 0.04 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:3.99 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:76.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:36982, 6563, 0.029
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6113
N(param)refined:471
Programs:CrysAlisPRO [1], SHELX [2], [3] , WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.99576(11)0.78924(9)0.30664(4)0.0374(2)
O10.7090(3)0.5151(3)0.00324(12)0.0370(6)
O20.5573(3)0.5863(3)0.08599(13)0.0342(5)
H2O0.480(8)0.551(8)0.054(3)0.16(4)*
C10.6993(4)0.5720(3)0.06257(16)0.0258(6)
C20.8567(4)0.6284(3)0.11016(16)0.0244(6)
C30.8490(4)0.6768(3)0.17820(16)0.0259(6)
H30.74290.67550.19510.031*
C40.9988(4)0.7269(3)0.22069(16)0.0285(7)
C51.1553(4)0.7277(3)0.19732(18)0.0312(7)
H51.25710.76110.22760.037*
C61.1614(4)0.6795(3)0.12970(18)0.0310(7)
H61.26800.68040.11320.037*
C71.0129(4)0.6296(3)0.08563(17)0.0285(6)
H71.01750.59650.03900.034*
S10.78621(9)0.40830(7)0.26149(3)0.02272(17)
S20.81972(9)0.50572(7)0.36157(3)0.02302(17)
O30.7184(3)0.3119(2)0.12761(10)0.0232(4)
O40.9046(3)0.2609(2)0.05497(10)0.0246(4)
H4O0.817(4)0.233(5)0.0272(18)0.056(14)*
O50.7639(3)0.6263(2)0.48620(10)0.0248(4)
O60.6717(3)0.5185(2)0.56095(10)0.0260(5)
H6O0.650(5)0.5964(19)0.5773(19)0.037(11)*
C80.8664(4)0.3090(3)0.11575(13)0.0192(5)
C91.0138(4)0.3573(3)0.16869(14)0.0194(5)
C101.1782(4)0.3535(3)0.15064(14)0.0222(6)
H101.19180.32230.10470.027*
C111.3216(4)0.3944(3)0.19857(15)0.0253(6)
H111.43220.39250.18570.030*
C121.3005(4)0.4381(3)0.26537(15)0.0247(6)
H121.39770.46420.29860.030*
C131.1398(4)0.4443(3)0.28459(14)0.0233(6)
H131.12830.47600.33070.028*
C140.9944(4)0.4043(3)0.23691(14)0.0207(6)
C150.8330(4)0.3744(3)0.40463(14)0.0211(6)
C160.8839(4)0.2504(3)0.37377(15)0.0249(6)
H160.91350.23660.32960.030*
C170.8916(4)0.1483(3)0.40669(16)0.0291(7)
H170.92440.06440.38460.035*
C180.8522(4)0.1664(3)0.47164(17)0.0297(7)
H180.85850.09590.49420.036*
C190.8031(4)0.2894(3)0.50334(16)0.0271(6)
H190.77590.30260.54780.033*
C200.7933(4)0.3934(3)0.47070(14)0.0215(6)
C210.7417(4)0.5228(3)0.50620(14)0.0213(6)
S30.53104(9)0.89128(7)0.74390(3)0.02117(16)
S40.56090(9)1.00475(7)0.84118(3)0.02130(16)
O70.5967(3)0.7603(2)0.61967(10)0.0255(4)
O80.6858(3)0.8659(2)0.54392(11)0.0305(5)
H8O0.708(6)0.787(2)0.529(2)0.066(16)*
O90.6257(3)1.1438(2)0.96992(10)0.0255(5)
O100.4396(3)1.2103(2)1.03995(10)0.0299(5)
H10O0.532(3)1.235(5)1.0652(19)0.057(14)*
C220.6135(4)0.8625(3)0.59818(14)0.0212(6)
C230.5560(4)0.9908(3)0.63037(14)0.0208(6)
C240.5439(4)1.0907(3)0.59503(15)0.0247(6)
H240.57821.07590.55160.030*
C250.4830(4)1.2109(3)0.62180(15)0.0265(6)
H250.47571.27810.59720.032*
C260.4331(4)1.2311(3)0.68499(16)0.0272(6)
H260.39051.31280.70380.033*
C270.4444(4)1.1336(3)0.72139(15)0.0240(6)
H270.40801.14910.76450.029*
C280.5084(4)1.0133(3)0.69551(14)0.0203(6)
C290.3519(4)1.0168(3)0.86387(14)0.0197(5)
C300.2075(4)0.9642(3)0.81723(14)0.0223(6)
H300.21980.92200.77220.027*
C310.0457(4)0.9726(3)0.83558(15)0.0245(6)
H31−0.05130.93720.80290.029*
C320.0246(4)1.0321(3)0.90117(16)0.0251(6)
H32−0.08631.03490.91380.030*
C330.1658(4)1.0873(3)0.94788(15)0.0229(6)
H330.15141.12950.99260.027*
C340.3309(4)1.0821(3)0.93034(13)0.0188(5)
C350.4784(4)1.1473(3)0.98131(13)0.0194(5)

Source of material

The title co-crystal was prepared through solvent drop grinding of 2-mercaptobenzoic acid (2-MBA; Merck) and 3-chlorobenzoic acid (ClBA; Merck) in a 1:1 molar ratio (0.001 mol, 0.154 g for 2-MBA and 0.157 g for ClBA). The mixture was ground for 15 min in the presence of few drops of methanol; the procedure was repeated three times. Colourless block crystals were obtained by carefully layering benzene (1.5 mL) on a dichloromethane (1.5 mL) solution of the ground co-crystal. M.p. (Hanon MP-450): 448.4–451.8 K. IR (Bruker Vertex 70v; cm−1): 3074–2819(w) ν(C—H), 1675(s) ν(C = O), 1597(s) and 1468(m) ν(C = C), 1414(s) δ(C—H), 740(s) δ(C—Cl).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The O-bound H-atoms were located in difference Fourier maps but were refined with a distance restraint of O—H = 0.84 ± 0.01 Å, and with Uiso(H) set to 1.5Ueq(O). Owing to poor agreement, three reflections, i.e. (1̄ 6̄ 3), (9̄ 4̄ 5) and (9̄ 4̄ 6), were omitted from the final cycles of refinement.

Comment

Owing to the presence of a central disulphide bond, 2-[(2-carboxyphenyl)disulfanyl]benzoic acid (2,2′-dithiobenzoic acid; DTBA), is a flexible dicarboxylic acid. This conformational flexibility is emphasized in a recent report of a tri-polymorphic inclusion compound formed between DTBA and trimethylamine [5]. Indeed, most studies of DTBA are motivated by co-crystal formation and it is of interest that sometimes DTBA found in co-crystals is a product of co-crystallisation experiments starting with 2-mercaptobenzoic acid (2-MBA) [6], [7] whereby 2-MBA is oxidised to DTBA. As a continuation of studies in this area [6, 8, 9], the title co-crystal was isolated from the attempted 1:1 co-crystallisation experiments between 2-MBA and a second carboxylic acid, namely 3-chlorobenzoic acid (3-ClBA).

X-ray diffraction showed the asymmetric unit in title co-crystal comprises two independent molecules of DTBA and one of 3-ClBA, indicating oxidation of 2-MBA had occurred during co-crystal formation. Confirmation that the molecule of 3-ClBA exists as a carboxylic acid is readily seen in the pattern of C1—O1, O2 bond lengths, i.e. 1.243(4) Å and 1.288(4) Å. A small twist from planarity is noted in the molecule. The r.m.s. deviation from the least-squares plane through the ring-carbon and chloride atoms being 0.0036 Å, and the dihedral angle between this plane and that through the carboxylic acid residue is 7.55(16)°. The crystal structure of 3-ClBA was originally reported in 1975 with a low temperature (105 K) redetermination of this P21/c polymorph [11] subsequently complimented by the report of a C2/c polymorph [12]. The comparable dihedral angles between C6/CO2 in these structures are 4.1(4)° [11] and 5.8(2)° [12].

The conformations of the two DTBA molecules comprising the asymmetric unit resemble each other as seen in the respective r.m.s. bond and angle fits of 0.0054 Å and 0.491° for the inverted-S1 and S3-molecules [13]; each lacks crystallographically imposed symmetry. The patterns in the C—O(hydroxy), O(carbonyl) bond lengths are consistent with the presence of carboxylic acid residues. The C6/CO2 dihedral angles are 3.7(3)° [O3-residue], 14.7(2)° [O5], 14.0(2)° [O7] and 4.1(2)° [O9]. This effectively co-planar relationship coupled with the observation each carbonyl-O atom is orientated towards the adjacent disulphide-S atom is indicative of attractive, hypervalent S ← O interactions [14]. The shortest such interaction in the present co-crystal structure is 2.675(2) Å for S4⋯O9 and the longest, 2.737(2) Å, for O3⋯O7. The twists in the molecules is best indicated by the C14—S1—S2—C15 and C28—S3—S4—C29 torsion angles of −91.06(15)° and 87.15(15)°, respectively, and the dihedral angles between the two phenyl rings in the S1- and S3-molecules, i.e. 79.54(11)° and 80.76(11)°, respectively. The crystal structure of the parent DTBA molecule has been determined and shows the asymmetric unit to comprise one and a half molecules, with the latter disposed about a 2-fold axis of symmetry [15]. The comparable C—S—S—C torsion and C6/CO2 dihedral angles are 86.12(14)° and 74.66(8)° for the molecule in the general position, and 87.90(13)° and 77.55(8)° for the symmetric molecule.

In the molecular packing, two distinct aggregation patterns based on conventional hydroxy-O—H⋯O(carbonyl) hydrogen bonding are discerned, each resulting in an eight-membered {⋯HOCO}2 synthon. In the first of these, centrosymmetrically-related two-molecule aggregates of 3-ClBA are formed [O2—H2o⋯O1i = 1.78(7) Å, O2⋯O1i = 2.608(4) Å with angle at H2o = 170(7)° for symmetry operation i: 1−x, 1−y, −z]. The second aggregate is a twisted, supramolecular chain comprising alternating S1- and S3-molecules [O4—H4o⋯O9ii = 1.84(4) Å, O4⋯O9ii = 2.665(3) Å with the angle at H4o = 170(5)°; O6—H6o⋯O7: 1.82(3) Å, 2.648(3) Å and 175(3)°; O8—H8o⋯O5: 1.80(3) Å, 2.633(3) Å and 171(4)°; O10—H10o⋯O3iii: 1.84(3) Å, 2.663(3) Å and 171(3)°, for ii: x, −1 + y, −1 + z and iii: x, 1 + y, 1 + z]. The chain is orientated along [0 1 1]. Connections between the aggregates mediated by hydrogen bonding include π-stacking interactions between (C2—C7)⋯(C9—C14) and (C2—C7)⋯(C29—C34)iv phenyl rings with ring-centroid separations of 3.6865(18) and 3.7344(18) Å, respectively. These interactions indicate the 3-ClBA molecule effectively bridges two independent DTBA molecules. The packing also features several parallel C=O⋯π interactions [16], [17] with C21=O5⋯π(C15—C20) presenting the shortest O⋯ring-centroid contact of 3.299(3) Å; the angle at O5 is 96.85(19)°.

Co-crystals of 3-ClBA with other carboxylic acids have not been reported and the sole example of a carboxylic acid co-crystal of DTBA is its 1:1 co-crystal with 2-MBA [7]. In the structure of this co-crystal, two DTBA molecules associate via hydroxy-O—H⋯O(carbonyl) hydrogen bonds leaving each of the outer carboxylic acid groups free to form eight-membered synthons with a 2-MBA molecule to result in the formation of a four-molecule aggregate.

Acknowledgements

Sunway University is thanked for support of crystal engineering studies (Grant No. INT-FST-RCCM-2016-01).

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Received: 2018-10-19
Accepted: 2019-01-14
Published Online: 2019-02-28
Published in Print: 2019-03-26

©2019 Sang Loon 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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  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
https://doi.org/10.1515/ncrs-2018-0442
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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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