Home Physical Sciences Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
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Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 1

Abstract

C22H20Cl2N2O3Sn, orthorhombic, P212121 (no. 19), a = 8.1234(3) Å, b = 10.7966(3) Å, c = 24.9785(8) Å, V = 2190.74(12) Å3, Z = 4, Rgt(F) = 0.0271, wRref(F2) = 0.0645, T = 293(2) K.

CCDC no.: 1947081

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:Yellow prism
Size:0.34 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.44 mm−1
Diffractometer, scan mode:Bruker SMART APEX, ω
θmax, completeness:28.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:22320, 5474, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5015
N(param)refined:275
Programs:Bruker [1], SHELX [2], [3], [4], WinGX/ORTEP [5]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.17317(3)0.22903(2)0.69021(2)0.03421(8)
Cl10.43522(14)0.26194(14)0.64689(5)0.0631(3)
Cl2−0.26747(19)0.82267(14)0.50698(5)0.0673(4)
O10.0522(4)0.3573(3)0.64287(12)0.0422(7)
O20.2677(4)0.1566(3)0.75814(13)0.0452(7)
O3−0.0685(4)0.2203(3)0.73642(12)0.0466(7)
H3O−0.086(7)0.165(4)0.7584(18)0.070*
N10.1300(4)0.5084(3)0.70246(13)0.0348(7)
N20.2007(4)0.4087(3)0.72955(13)0.0333(7)
C10.0588(5)0.4722(4)0.65833(16)0.0332(8)
C2−0.0223(5)0.5623(4)0.62262(16)0.0346(8)
C3−0.0024(6)0.6888(4)0.62771(17)0.0407(9)
H30.06310.72000.65510.049*
C4−0.0784(5)0.7694(4)0.59270(16)0.0448(9)
H4−0.06520.85450.59660.054*
C5−0.1744(5)0.7225(4)0.55173(15)0.0437(8)
C6−0.1948(7)0.5993(5)0.5457(2)0.0618(14)
H6−0.26060.56930.51810.074*
C7−0.1175(6)0.5165(4)0.5806(2)0.0556(13)
H7−0.12960.43160.57590.067*
C80.2941(5)0.4313(4)0.77008(16)0.0359(9)
H80.30930.51390.77950.043*
C90.3766(5)0.3397(4)0.80190(17)0.0362(9)
C100.3631(5)0.2102(4)0.79500(16)0.0394(10)
C110.4515(6)0.1316(5)0.82922(19)0.0476(11)
H110.44530.04620.82460.057*
C120.5475(6)0.1796(6)0.8696(2)0.0552(13)
H120.60600.12600.89170.066*
C130.5586(6)0.3054(5)0.8780(2)0.0549(13)
H130.62140.33640.90610.066*
C140.4758(6)0.3843(5)0.84428(18)0.0459(10)
H140.48520.46930.84950.055*
C15−0.2044(6)0.3034(5)0.7391(2)0.0617(14)
H15A−0.16550.38490.74790.093*
H15B−0.28000.27580.76620.093*
H15C−0.25930.30560.70510.093*
C160.0936(6)0.0631(4)0.64952(17)0.0382(9)
H16A0.18870.01250.64090.046*
H16B0.02250.01550.67300.046*
C170.0025(6)0.0943(4)0.59894(19)0.0441(10)
C180.0817(7)0.1017(5)0.5497(2)0.0585(13)
H180.19520.09060.54820.070*
C19−0.0033(9)0.1249(5)0.5034(2)0.0644(14)
H190.05280.12830.47100.077*
C20−0.1685(9)0.1430(5)0.5044(2)0.0707(15)
H20−0.22570.15870.47280.085*
C21−0.2514(7)0.1379(6)0.5533(2)0.0654(15)
H21−0.36460.15050.55450.078*
C22−0.1665(7)0.1146(4)0.5989(2)0.0524(11)
H22−0.22320.11220.63130.063*

Source of material

The melting point was measured on a Electrothermal digital melting point apparatus and was uncorrected. The elemental analysis was performed on a Perkin-Elmer EA2400 CHN analyser. The IR spectrum was recorded using a Perkin-Elmer RX1 spectrophotometer equipped as a Nujol mull in a KBr cell from 4000 to 400 cm−1. The 1H NMR spectrum was recorded in DMSO-d6 solution on a Jeol JNM-ECA 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

Dibenzyltin dichloride was synthesized by the direct reaction of benzyl chloride (Merck) and metallic tin powder (Merck) in toluene according to a literature procedure [6]. The hydrazone ligand was prepared by the condensation of salicylaldehyde (Sigma Aldrich, 0.55 mL, 5.0 mmol) and 4-chlorobenzhydrazide (Sigma Aldrich, 0.86 g, 5.0 mmol) in hot methanol (25 mL). Dibenzyltin dichloride (0.37 g, 1 mmol) and the ligand (0.28 g, 1.0 mmol) were dissolved in methanol (30 mL). The mixture was refluxed for 2 h and filtered. The filtrate was allowed to stand at room temperature where upon yellow crystals were obtained from slow evaporation. The product was filtered, washed with minimum amount of methanol and air-dried. Yield: 0.34 g (62.2%). M.pt: 495–497 K. Anal. Calc. for C23H19Cl2N2O3Sn: C 49.09; H 3.38; N 4.98%. Found: C 49.12; H 3.75; N 5.25%. IR (cm−1) 1610 (s) ν(C—N), 1542 (s) ν(C—O). 1H NMR (DMSO-d6, p.p.m.): δ 3.10 (s, 2H, CH2), 3.47 (s, 3H, CH3), 6.85 (d, 2H, J = 7.7 Hz, Ph—H), 7.15–7.38 (m, 5H, Ph—H), 7.42 (d, 2H, J = 7.8 Hz, Ph—H), 7.62 (d, 2H, J = 8.0 Hz, Ph—H), 8.04 (d, 2H, J = 8.0 Hz, Ph—H), 8.83 (s, 1H, N=CH); OH not observed.

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The O-bound H-atom was located in a difference Fourier map but was refined with a distance restraint O—H = 0.82 ± 0.01 Å, and with Uiso(H) set to 1.5Ueq(O). The absolute structure was determined based on differences in Friedel pairs [4].

Comment

The motivation of on-going investigations on organotin compounds featuring a tridentate hydrazone ligand related to that in the title compound arise as a result of their potential as chemotherapeutic agents [7], [8], [9], [10], a well known attribute of organotin compounds [11]. In continuation of structural studies in this area [12], [13], [14], [15], [16], the title organotin hydrazone, (I), has been investigated by X-ray crystallography.

The molecular structure of the title compound (I) is shown in the figure (35% displacement ellipsoids) and features a tin atom coordinated by the dianionic, tridentate hydrazone ligand, via the oxide-O1, phenoxide-O2 and imine-N2 atoms, a chloride, a methylene-carbon atom of the benzyl substitutent and a methanol molecule. The resultant CClNO3 coordination geometry is based on an octahedron. Deviations from the ideal 180° angle are observed O1—Sn—O2 [156.86(12)°], N2—Sn—C16 [168.16(15)°] and Cl1—Sn—O3 [172.98(10)°]. These deviations are related, to a large extent, to the acute bite angles subtended at the tin atom by the five- and six-membered chelate rings. Thus, O1—Sn—N2 is 73.24(11)° and O2—Sn—N2 is 85.81(12)°. The N,O,O donor atoms of the tridentate ligand occupy mer-positions in the octahedron. The Sn—O1(oxide) and Sn—O2(phenoxide) bond lengths of 2.069(3) and 2.020(3) Å are not greatly different and each is shorter, as expected, than the Sn—O3(methanol) bond length of 2.279(3) Å. The Sn—N2 bond length is 2.186(3) Å, while those of Sn—Cl1 and Sn—C16 are 2.4143(11) and 2.159(4) Å, respectively. There is considerable delocalization of π-electron density over the O1—C1—N1—N2—C8 chromophore as seen in the C1—O1 [1.300(5) Å], C1—N1 [1.305(5) Å], N1—N2 [1.395(4) Å] and C8—N2 [1.288(5) Å] bond lengths. As indicated above, the chelating mode of the tridentate hydrazone ligand leads to the formation of five- and six-membered rings. The r.m.s. deviation of the five fitted atoms of the five-membered chelate ring is 0.0128 Å with the maximum deviation being 0.018(2) Å for the O1 atom. By contrast to this planar chelate ring, the r.m.s. deviation of the six atoms comprising the six-membered chelate ring = 0.1048 Å, with the maximum deviation of 0.154(2) Å being for the O2 atom. Thus, the six-membered ring is best described as being an envelope with the O2 atom lying 0.288(4) Å out of the least-squares plane defined by the five remaining atoms [r.m.s. deviation = 0.0658 Å]. The chelate rings are approximately co-planar with the dihedral angle between these being 6.2(2)°. The dihedral angle between the five-membered ring and the appended phenyl ring is 11.7(2)°, and the dihedral angle between the six-membered chelate ring and attached phenyl ring is 5.7(2)°, indicating an effectively co-planar relationship. The benzyl substituent is folded to lie over the hydrazone residue and the dihedral angle between it and each of the best planes through the five- and six-membered chelate rings are 78.24(14) and 84.39(15)°, respectively, again indicating an approximately orthogonal disposition in each case.

A very similar coordination geometry to that reported herein has been observed previously in the structure of chlorido-(4-chloro-N-[(4-methoxy-2-oxidophenyl)methylidene] benzenecarbohydrazonato)-(4-fluorobenzyl)-methanol-tin(IV) [10]. The title compound is the product in the attempt to synthesize complex molecules of the general formula di-(substituted-benzyl)tin(Ln), where H2Ln is a substituted hydrazone molecule, from the reaction of di-(substituted-benzyl)tin dichloride with H2Ln. While such species, e.g. (2-FC6H4CH2)2Sn(L1), where H2L1 is 4-chloro-N′-[(1E)-(5-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, can be formed [16], other incomplete reaction products are also sometimes obtained, e.g. (4-FC6H4CH2)Sn(OH2)(L3)Cl, where H2L3 is 1-hydroxy-N′-[(1E)-(2-hydroxy-4-methoxyphenyl)methylidene] naphthalene-2-carbohydrazide [15]. Clearly, the nature of the ultimate reaction product is highly dependent on the reaction conditions and reagents employed.

The key feature of the molecular packing is the formation of a helical supramolecular chain along the b axis direction mediated by methanol-O—H⋯N(imine) hydrogen bonding [O3—H3o⋯N1i: H3o⋯N1i = 1.99(4) Å, O3⋯N1i = 2.795(5) Å with angle at H3o = 170(5)° for symmetry operation (i) − x, −1/2 + y, 3/2 – z]. The chains are connected into a layer in the ab-plane by a combination of π—π stacking interactions between the two different phenyl moieties of the hydrazone ligand [Cg(C2—C7)⋯Cg(C9—C14)ii = 3.738(3) Å with angle of inclination = 1.6(2)° for (ii) − x, 1/2 + y, 3/2 − z] and C—H⋯π(phenyl) [C15—H15b⋯Cg(C9—C14)iii: H15b⋯Cg(C9—C14)iii = 2.74 Å, C15⋯Cg(C9—C14)iii = 3.670(5) Å with angle at H15b = 164° for (iii) −1 + x, y, z] interactions. The intermolecular links along the c axis to consolidate a three-dimensional architecture are end-on and side-on C—Cl⋯π(phenyl) interactions involving the same hydrazone-bound chloride atom interacting with two different rings [C5—Cl2⋯Cg(C2–C7)iv: Cl2⋯Cg(C2—C7)iv = 3.585(2) Å, C5⋯Cg(C2—C7)iv 5.093(4) Å with angle at Cl2 = 144.56(16)° and C5—Cl2⋯Cg(C17—C22)v: Cl2⋯Cg(C17—C22)v = 3.703(3) Å, C5⋯Cg(C17—C22)v = 4.347(5) Å with angle at Cl2 = 99.88(15)° for (iv) −1/2 + x, 3/2 − y, 1 − z and (v) x, 1 + y, z].

An analysis of the molecular packing was conducted by calculating the Hirshfeld surface to determine the major percentage contributors to the surface. This was conducted with Crystal Explorer 17 [17] in accord with standard procedures [18]; accordingly, the Hirshfeld surfaces were calculated as were the full and delineated two-dimensional fingerprint plots. The greatest percentage contribution to the surface contacts come from H⋯H [46.7%] with significant contributions, not unexpectedly, from Cl⋯H/H⋯Cl [17.7%] and C⋯H/H⋯C [16.5%] contacts, reflecting the discussion above. Other notable percentage contributors are Cl⋯C/C⋯Cl [6.2%], O⋯H/H⋯O [4.1%], C⋯C [4.0%] and N⋯H/H⋯N [3.9%] contacts.

Acknowledgements

Sunway University Sdn Bhd is thanked for financial support of this work through Grant No. STR-RCTR-RCCM-001–2019.

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Received: 2019-07-25
Accepted: 2019-08-14
Published Online: 2019-09-17
Published in Print: 2019-12-18

©2019 See Mun Lee 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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  33. Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
  34. Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
  35. The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
  36. Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
  37. Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
  38. Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
  39. Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
  40. Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
  41. Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
  42. Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
  43. Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
  44. Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
  45. Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
  46. Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
  47. Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
  48. Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
  49. Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
  50. Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
  51. Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
  52. Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
  53. Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
  54. Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
  55. Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
  56. Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
https://doi.org/10.1515/ncrs-2019-0530
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Articles in the same Issue

  1. 10.1515/ncrs-2020-frontmatter1
  2. The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
  3. The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
  4. Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
  5. Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
  6. The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
  7. Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
  8. Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  9. Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
  10. The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
  11. Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
  12. Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
  13. The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
  14. Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
  15. The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
  16. The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
  17. The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
  18. The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
  19. Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
  20. Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
  21. The crystal structure of catena-poly(μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
  22. Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
  23. Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
  24. Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
  25. Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
  26. Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
  27. Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
  28. Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
  29. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
  30. The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
  31. Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
  32. Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
  33. Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
  34. Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
  35. The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
  36. Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
  37. Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
  38. Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
  39. Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
  40. Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
  41. Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
  42. Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
  43. Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
  44. Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
  45. Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
  46. Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
  47. Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
  48. Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
  49. Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
  50. Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
  51. Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
  52. Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
  53. Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
  54. Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
  55. Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
  56. Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
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