Home Physical Sciences Crystal structure of bis[(((4-fluorophenyl)amino)methyl)triphenylphosphonium] tetrachloridocobaltate(II), C50H44Cl4CoF2N2P2
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Crystal structure of bis[(((4-fluorophenyl)amino)methyl)triphenylphosphonium] tetrachloridocobaltate(II), C50H44Cl4CoF2N2P2

  • S. Kanchanadevi , Frank R. Fronczek , V. Arun and V. Mahalingam EMAIL logo
Published/Copyright: January 24, 2019

Abstract

C50H44Cl4CoF2N2P2, orthorhombic, Pbca (no. 61), a = 18.4662(6) Å, b = 15.2888(5) Å, c = 33.2661(10) Å, V = 9391.9(5) Å3, Z = 8, Rgt(F) = 0.0403, wRref(F2) = 0.1005, T = 180.0(5) K.

CCDC no.: 1855274

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Blue fragment
Size:0.40 × 0.34 × 0.33 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.71 mm−1
Diffractometer, scan mode:Bruker Kappa APEX-II DUO CCD, φ and ω
θmax, completeness:28.9°, >99%
N(hkl)measured, N(hkl)unique, Rint:198347, 12366, 0.043
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 10091
N(param)refined:556
Programs:Bruker [1], [2] , SHELX [3], [4]
Table 2:

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

AtomxyzUiso*/Ueq
Co10.13917(2)0.48030(2)0.37476(2)0.03734(7)
Cl10.04392(2)0.38797(3)0.35873(2)0.03274(10)
Cl20.14222(3)0.49633(3)0.44253(2)0.03928(11)
Cl30.24069(3)0.41119(5)0.35304(2)0.05812(17)
Cl40.12414(6)0.60710(5)0.34281(3)0.1031(4)
P10.19516(2)0.20962(3)0.26076(2)0.03027(10)
F1−0.01012(7)−0.08440(9)0.40520(4)0.0528(3)
N10.10579(8)0.19899(11)0.32431(5)0.0326(3)
H1N0.0911(12)0.2470(15)0.3343(7)0.039*
C10.18233(10)0.20545(13)0.31515(5)0.0325(4)
H1C0.20820.15420.32630.039*
H1D0.20260.25890.32760.039*
C20.07739(9)0.12505(12)0.34398(5)0.0291(4)
C30.10529(11)0.04163(13)0.33886(6)0.0372(4)
H30.14500.03270.32120.045*
C40.07583(11)−0.02901(14)0.35935(6)0.0394(4)
H40.0956−0.08590.35620.047*
C50.01777(10)−0.01538(14)0.38425(6)0.0370(4)
C6−0.01245(10)0.06585(14)0.38938(6)0.0343(4)
H6−0.05340.07360.40630.041*
C70.01777(9)0.13622(13)0.36940(5)0.0301(4)
H7−0.00220.19290.37300.036*
C80.15004(9)0.30263(12)0.23955(5)0.0311(4)
C90.13642(10)0.37591(13)0.26295(6)0.0336(4)
H90.14760.37550.29080.040*
C100.10635(11)0.44996(14)0.24542(7)0.0398(4)
H100.09720.50040.26130.048*
C110.08972(12)0.45054(15)0.20499(7)0.0459(5)
H110.06820.50090.19330.055*
C120.10427(15)0.37819(17)0.18154(7)0.0529(6)
H120.09340.37910.15360.063*
C130.13460(13)0.30449(15)0.19856(6)0.0451(5)
H130.14500.25500.18230.054*
C140.28984(10)0.21847(14)0.24911(7)0.0402(5)
C150.31398(15)0.19241(18)0.21142(9)0.0667(8)
H150.28110.16790.19260.080*
C160.38613(19)0.2024(2)0.20160(13)0.0866(12)
H160.40290.18490.17580.104*
C170.43360(15)0.2371(2)0.22871(12)0.0893(13)
H170.48340.24230.22190.107*
C180.40992(13)0.2646(3)0.26557(11)0.0919(13)
H180.44310.28970.28410.110*
C190.33721(12)0.2557(2)0.27605(8)0.0661(8)
H190.32050.27520.30150.079*
C200.15970(11)0.11195(13)0.23911(6)0.0352(4)
C210.08895(12)0.10882(15)0.22442(6)0.0423(5)
H210.05950.15970.22510.051*
C220.06170(14)0.03189(17)0.20889(7)0.0519(6)
H220.01360.03000.19870.062*
C230.10399(17)−0.04192(18)0.20806(8)0.0620(7)
H230.0853−0.09470.19710.074*
C240.17352(17)−0.03969(17)0.22303(9)0.0653(7)
H240.2022−0.09120.22260.078*
C250.20192(14)0.03669(15)0.23863(8)0.0514(6)
H250.24990.03780.24890.062*
P20.48848(3)0.78152(3)0.50573(2)0.03103(10)
F20.83431(8)0.94565(16)0.41007(6)0.0913(6)
N20.55148(9)0.84922(12)0.43969(5)0.0367(4)
H2N0.5273(13)0.8537(16)0.4192(7)0.044*
C260.51224(10)0.87635(12)0.47507(6)0.0340(4)
H26A0.46760.90760.46700.041*
H26B0.54240.91710.49100.041*
C270.62414(10)0.87217(12)0.43354(6)0.0319(4)
C280.67038(11)0.89506(14)0.46470(6)0.0373(4)
H280.65340.89390.49170.045*
C290.74114(12)0.91956(16)0.45662(7)0.0483(5)
H290.77270.93610.47790.058*
C300.76493(11)0.91963(19)0.41791(8)0.0550(6)
C310.72192(13)0.89376(19)0.38657(7)0.0552(6)
H310.74030.89260.35990.066*
C320.65160(11)0.86951(16)0.39445(6)0.0440(5)
H320.62130.85070.37300.053*
C330.43802(11)0.81987(13)0.54829(6)0.0360(4)
C340.37080(12)0.78393(15)0.55741(7)0.0451(5)
H340.35200.73720.54180.054*
C350.33147(14)0.81685(18)0.58949(8)0.0549(6)
H350.28550.79250.59580.066*
C360.35848(14)0.88467(17)0.61227(7)0.0542(6)
H360.33120.90670.63430.065*
C370.42480(15)0.92055(16)0.60320(7)0.0537(6)
H370.44320.96740.61890.064*
C380.46480(13)0.88881(15)0.57136(7)0.0466(5)
H380.51050.91390.56520.056*
C390.57041(10)0.72839(13)0.52012(7)0.0418(5)
C400.61079(13)0.68662(14)0.49027(10)0.0561(7)
H400.59340.68330.46340.067*
C410.67736(15)0.64991(16)0.50087(13)0.0789(11)
H410.70630.62170.48110.095*
C420.70109(15)0.65484(19)0.54053(15)0.0893(13)
H420.74590.62880.54780.107*
C430.66123(16)0.6963(2)0.56906(13)0.0839(11)
H430.67870.69960.59590.101*
C440.59570(13)0.73346(17)0.55941(9)0.0588(7)
H440.56790.76240.57940.071*
C450.43316(10)0.70808(13)0.47737(6)0.0345(4)
C460.38260(11)0.74060(15)0.45014(7)0.0415(5)
H460.38010.80150.44470.050*
C470.33581(12)0.68283(18)0.43100(7)0.0515(6)
H470.30110.70440.41240.062*
C480.33943(13)0.59433(18)0.43887(8)0.0560(7)
H480.30700.55530.42580.067*
C490.38998(13)0.56233(16)0.46562(8)0.0527(6)
H490.39280.50120.47060.063*
C500.43664(12)0.61866(14)0.48529(7)0.0426(5)
H500.47080.59660.50410.051*

Source of material

An ethanol solution of [CoCl2(PPH3)2] (0.2 mmol) in ethanol (25 mL) and the Schiff base 2-[(4-flurophenylimino)-methyl]-phenol (0.2 mmol) in 1:1 molar ratio was added and heated under reflux in a round bottom flask fitted with a double surface condenser for 6 h. The solution was then concentrated on the water bath to 3 mL and cooled. The product {bis[(((4-fluorophenyl)amino)methyl)triphenylphosphonium] tetrachloridocobaltate(II)} was precipitated by the addition of small quantity of petroleum ether (60−80 °C) and recrystallized from CH2Cl2/petroleum ether and dried in vacuum (Yield-70−16%). Anal. calcd. for C50H44CoN2P2F2Cl4(%): C,61.68; H,4.55; N,2.87. Found (%): C, 61.63; H, 4.25; N, 2.75.

Experimental details

Hydrogen atoms were treated by a mixture of independent and constrained refinement. Coordinates for NH hydrogen atoms were refined, while those on C were placed in idealized positions. Uiso values for H were assigned as 1.2 time the Ueq values for the atoms to which they are bonded.

Comment

Schiff base ligands play a vital role in preparation of synthetic drugs and biological processes. These bioactive compounds have attracted their attention in the field of anticancer [5], [6] anti malarial [7], [8] and various clinical and pharmacological areas [9], [10], [11], [12], [13]. They gained attraction in the field of super capacitors, organic solar cells, electro chromic materials, organic light-emitting diodes and nonlinear optic materials [14], [15], [16], [17], [18], [19].

The asymmetric unit of the title structure contains, two phosphonium cations and one tetrachloridocobaltate(II) dianion (see the figure). The bond lengths and angles within these moieties are in the expected ranges.

The four chlorido ligands (Cl1—Cl4) of the tetrachloridocobaltate(II) anion show Co—Cl distances ranging from 2.2282(7) Å to 2.3175(5) Å whereas the Co—Cl4 bond length with 2.2282(7) Å is the shortest of them.

This finding is in accord with the hydrogen bonding scheme of the title structure. The chlorido ligands Cl1 and Cl2 form classical NH⋯Cl hydrogen bonds. The chlorido ligand Cl4 does not form any hydrogen bond and additionally shows a large amplitude of the displacement ellipsoid perpendicular to the Co–Cl bond, furthermore artefactually reducing the derived bond length (see the figure).

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Received: 2018-08-06
Accepted: 2018-12-17
Published Online: 2019-01-24
Published in Print: 2019-03-26

©2019 S. Kanchanadevi 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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  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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