Literature DB >> 22064276

10-Hy-droxy-benzo[h]quinolinium tetra-chlorido(2-methyl-quinolin-8-olato-κN,O)stannate(IV) methanol disolvate.

Ezzatollah Najafi, Marzieh Vafaee, Mostafa M Amini, Seik Weng Ng.   

Abstract

In the disolvated title salt, (C(13)H(10)NO)[SnCl(4)(C(10)H(8)NO)]·2CH(3)OH, the Sn(IV) atom is chelated by the N,O-bidentate 2-methyl-quinolin-8-olate ion and is further coordinated by four chloride ions, showing a distorted octa-hedral SnNOCl(4) geometry. In the crystal, the cation and anion are linked to the methanol mol-ecules by O-H⋯O and N-H⋯O hydrogen bonds.

Entities:  

Year:  2011        PMID: 22064276      PMCID: PMC3200771          DOI: 10.1107/S1600536811031461

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the related compound, solvated 2-methyl-8-hy­droxy­quinolinium tetra­chlorido(quinolin-8-olato)stannate(IV), see: Vafaee et al. (2010 ▶).

Experimental

Crystal data

(C13H10NO)[SnCl4(C10H8NO)]·2CH4O M = 678.97 Triclinic, a = 7.5645 (2) Å b = 10.1112 (3) Å c = 17.7837 (5) Å α = 98.105 (3)° β = 95.653 (3)° γ = 97.509 (3)° V = 1325.56 (6) Å3 Z = 2 Mo Kα radiation μ = 1.40 mm−1 T = 100 K 0.30 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.678, T max = 0.873 10548 measured reflections 5871 independent reflections 5239 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.095 S = 1.11 5871 reflections 340 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 1.23 e Å−3 Δρmin = −1.14 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031461/xu5283sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031461/xu5283Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C13H10NO)[SnCl4(C10H8NO)]·2CH4OZ = 2
Mr = 678.97F(000) = 680
Triclinic, P1Dx = 1.701 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5645 (2) ÅCell parameters from 6565 reflections
b = 10.1112 (3) Åθ = 2.3–29.3°
c = 17.7837 (5) ŵ = 1.40 mm1
α = 98.105 (3)°T = 100 K
β = 95.653 (3)°Prism, yellow
γ = 97.509 (3)°0.30 × 0.30 × 0.10 mm
V = 1325.56 (6) Å3
Agilent SuperNova Dual diffractometer with an Atlas detector5871 independent reflections
Radiation source: SuperNova (Mo) X-ray Source5239 reflections with I > 2σ(I)
MirrorRint = 0.056
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.5°
ω scansh = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)k = −10→12
Tmin = 0.678, Tmax = 0.873l = −22→23
10548 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0329P)2 + 1.5116P] where P = (Fo2 + 2Fc2)/3
5871 reflections(Δ/σ)max = 0.001
340 parametersΔρmax = 1.23 e Å3
4 restraintsΔρmin = −1.14 e Å3
xyzUiso*/Ueq
Sn10.86883 (3)0.09428 (2)0.789295 (13)0.01747 (8)
Cl10.86363 (16)−0.14417 (9)0.78823 (6)0.0417 (3)
Cl20.63271 (12)0.06051 (9)0.68485 (5)0.02469 (19)
Cl30.66698 (12)0.09658 (10)0.88638 (5)0.0303 (2)
Cl41.10456 (13)0.09761 (11)0.70839 (5)0.0340 (2)
O10.8665 (3)0.2980 (2)0.78929 (13)0.0164 (5)
O20.3798 (4)0.4948 (3)0.64356 (15)0.0274 (6)
H20.453 (5)0.464 (4)0.672 (2)0.041*
O30.5605 (3)0.4044 (3)0.75020 (15)0.0261 (6)
H30.649 (4)0.363 (4)0.752 (3)0.039*
O40.4163 (4)0.7760 (3)0.73826 (19)0.0459 (8)
H40.507 (5)0.836 (4)0.749 (3)0.069*
N11.0833 (4)0.1902 (3)0.88721 (15)0.0165 (6)
N20.2612 (4)0.6931 (3)0.58555 (18)0.0226 (6)
H10.304 (5)0.673 (4)0.6302 (12)0.027*
C11.0870 (4)0.3279 (3)0.89787 (19)0.0164 (7)
C20.9706 (4)0.3813 (3)0.84513 (19)0.0165 (7)
C30.9725 (5)0.5190 (3)0.8541 (2)0.0210 (7)
H3A0.89640.55640.81970.025*
C41.0860 (5)0.6053 (4)0.9140 (2)0.0240 (8)
H4A1.08430.69990.91910.029*
C51.1982 (5)0.5561 (4)0.9646 (2)0.0229 (7)
H51.27400.61591.00430.028*
C61.2003 (4)0.4154 (3)0.95736 (19)0.0192 (7)
C71.3109 (5)0.3538 (4)1.0069 (2)0.0234 (8)
H71.38810.40781.04840.028*
C81.3067 (5)0.2178 (4)0.9950 (2)0.0254 (8)
H81.38210.17731.02810.031*
C91.1914 (5)0.1355 (4)0.9339 (2)0.0213 (7)
C101.1918 (6)−0.0137 (4)0.9208 (2)0.0320 (9)
H10A1.2077−0.04330.86730.048*
H10B1.0775−0.05960.93210.048*
H10C1.2907−0.03600.95430.048*
C110.2292 (4)0.6061 (4)0.5177 (2)0.0189 (7)
C120.2715 (4)0.4711 (4)0.5116 (2)0.0202 (7)
C130.3479 (4)0.4138 (4)0.5739 (2)0.0215 (7)
C140.3861 (5)0.2837 (4)0.5632 (2)0.0245 (8)
H140.43540.24650.60530.029*
C150.3524 (5)0.2065 (4)0.4906 (2)0.0256 (8)
H150.38100.11710.48350.031*
C160.2783 (5)0.2574 (4)0.4289 (2)0.0256 (8)
H160.25630.20320.37980.031*
C170.2354 (4)0.3891 (4)0.4384 (2)0.0214 (7)
C180.1589 (5)0.4437 (4)0.3745 (2)0.0263 (8)
H180.13620.38890.32560.032*
C190.1186 (5)0.5699 (4)0.3819 (2)0.0262 (8)
H190.06540.60170.33850.031*
C200.1542 (4)0.6568 (4)0.4535 (2)0.0222 (7)
C210.1174 (5)0.7900 (4)0.4624 (2)0.0295 (9)
H210.06810.82460.41930.035*
C220.1518 (5)0.8716 (4)0.5327 (2)0.0288 (8)
H220.12530.96150.53880.035*
C230.2259 (5)0.8189 (4)0.5943 (2)0.0290 (8)
H230.25170.87350.64320.035*
C240.4551 (6)0.3602 (4)0.8063 (2)0.0329 (9)
H24A0.52700.38070.85660.049*
H24B0.41630.26260.79350.049*
H24C0.34960.40690.80750.049*
C250.4131 (7)0.7114 (5)0.8025 (2)0.0414 (10)
H25A0.52180.66910.80940.062*
H25B0.30700.64200.79550.062*
H25C0.40830.77770.84790.062*
U11U22U33U12U13U23
Sn10.02318 (13)0.01235 (12)0.01641 (13)0.00327 (9)−0.00053 (9)0.00207 (8)
Cl10.0566 (7)0.0134 (4)0.0472 (6)0.0041 (4)−0.0256 (5)0.0014 (4)
Cl20.0283 (4)0.0200 (4)0.0237 (4)0.0035 (3)−0.0062 (4)0.0027 (3)
Cl30.0279 (5)0.0373 (5)0.0282 (5)−0.0008 (4)0.0084 (4)0.0156 (4)
Cl40.0331 (5)0.0530 (6)0.0187 (4)0.0224 (5)0.0053 (4)−0.0007 (4)
O10.0193 (11)0.0139 (11)0.0167 (11)0.0049 (9)0.0023 (9)0.0027 (9)
O20.0339 (15)0.0294 (15)0.0213 (14)0.0096 (12)−0.0004 (12)0.0102 (11)
O30.0230 (13)0.0351 (15)0.0266 (14)0.0133 (11)0.0089 (11)0.0143 (11)
O40.0452 (18)0.049 (2)0.0390 (18)−0.0141 (15)−0.0075 (15)0.0209 (15)
N10.0194 (13)0.0164 (14)0.0144 (14)0.0025 (11)0.0040 (11)0.0031 (11)
N20.0192 (14)0.0256 (16)0.0242 (16)0.0015 (13)0.0018 (13)0.0104 (13)
C10.0184 (15)0.0135 (15)0.0180 (16)−0.0004 (13)0.0074 (13)0.0036 (12)
C20.0167 (15)0.0177 (16)0.0167 (16)0.0029 (13)0.0083 (13)0.0039 (12)
C30.0242 (17)0.0179 (17)0.0240 (18)0.0047 (14)0.0099 (15)0.0078 (14)
C40.0272 (18)0.0135 (16)0.032 (2)0.0002 (14)0.0135 (16)0.0024 (14)
C50.0218 (17)0.0196 (18)0.0244 (19)−0.0027 (14)0.0071 (15)−0.0042 (14)
C60.0171 (16)0.0209 (17)0.0186 (17)−0.0020 (13)0.0088 (14)−0.0001 (13)
C70.0196 (17)0.029 (2)0.0192 (18)0.0016 (15)0.0024 (14)−0.0036 (14)
C80.0246 (18)0.029 (2)0.0218 (18)0.0049 (16)−0.0029 (15)0.0050 (15)
C90.0249 (17)0.0204 (18)0.0192 (17)0.0047 (14)0.0020 (14)0.0047 (13)
C100.040 (2)0.0217 (19)0.032 (2)0.0077 (17)−0.0115 (18)0.0049 (16)
C110.0128 (15)0.0243 (18)0.0214 (18)0.0013 (13)0.0046 (13)0.0090 (14)
C120.0129 (15)0.0285 (19)0.0222 (18)0.0034 (14)0.0064 (14)0.0109 (14)
C130.0182 (16)0.0268 (19)0.0217 (18)0.0034 (14)0.0051 (14)0.0089 (14)
C140.0200 (17)0.029 (2)0.029 (2)0.0058 (15)0.0065 (15)0.0139 (15)
C150.0227 (18)0.0247 (19)0.033 (2)0.0053 (15)0.0108 (16)0.0089 (15)
C160.0238 (18)0.031 (2)0.0235 (19)0.0039 (16)0.0095 (15)0.0048 (15)
C170.0166 (16)0.0291 (19)0.0215 (18)0.0039 (14)0.0079 (14)0.0100 (14)
C180.0283 (19)0.036 (2)0.0170 (17)0.0049 (16)0.0064 (15)0.0081 (15)
C190.0215 (17)0.040 (2)0.0220 (19)0.0068 (16)0.0067 (15)0.0156 (16)
C200.0170 (16)0.030 (2)0.0236 (18)0.0041 (14)0.0071 (14)0.0135 (15)
C210.0214 (18)0.038 (2)0.035 (2)0.0083 (17)0.0081 (17)0.0216 (18)
C220.0288 (19)0.027 (2)0.034 (2)0.0071 (16)0.0080 (17)0.0113 (16)
C230.0278 (19)0.024 (2)0.036 (2)0.0037 (16)0.0039 (17)0.0075 (16)
C240.037 (2)0.034 (2)0.034 (2)0.0086 (18)0.0181 (18)0.0113 (17)
C250.055 (3)0.037 (2)0.033 (2)0.006 (2)0.009 (2)0.0052 (19)
Sn1—O12.063 (2)C9—C101.494 (5)
Sn1—N12.272 (3)C10—H10A0.9800
Sn1—Cl42.3988 (10)C10—H10B0.9800
Sn1—Cl22.4011 (8)C10—H10C0.9800
Sn1—Cl12.4036 (9)C11—C201.414 (5)
Sn1—Cl32.4145 (9)C11—C121.435 (5)
O1—C21.324 (4)C12—C171.422 (5)
O2—C131.366 (4)C12—C131.429 (5)
O2—H20.843 (10)C13—C141.375 (5)
O3—C241.421 (5)C14—C151.393 (5)
O3—H30.835 (10)C14—H140.9500
O4—C251.395 (5)C15—C161.376 (5)
O4—H40.838 (10)C15—H150.9500
N1—C91.333 (4)C16—C171.403 (5)
N1—C11.374 (4)C16—H160.9500
N2—C231.325 (5)C17—C181.436 (5)
N2—C111.369 (5)C18—C191.342 (5)
N2—H10.888 (10)C18—H180.9500
C1—C61.413 (5)C19—C201.423 (5)
C1—C21.433 (5)C19—H190.9500
C2—C31.377 (5)C20—C211.401 (5)
C3—C41.412 (5)C21—C221.380 (6)
C3—H3A0.9500C21—H210.9500
C4—C51.366 (5)C22—C231.385 (5)
C4—H4A0.9500C22—H220.9500
C5—C61.413 (5)C23—H230.9500
C5—H50.9500C24—H24A0.9800
C6—C71.418 (5)C24—H24B0.9800
C7—C81.358 (5)C24—H24C0.9800
C7—H70.9500C25—H25A0.9800
C8—C91.415 (5)C25—H25B0.9800
C8—H80.9500C25—H25C0.9800
O1—Sn1—N177.28 (9)C9—C10—H10C109.5
O1—Sn1—Cl490.31 (7)H10A—C10—H10C109.5
N1—Sn1—Cl486.85 (7)H10B—C10—H10C109.5
O1—Sn1—Cl286.01 (6)N2—C11—C20116.6 (3)
N1—Sn1—Cl2163.26 (7)N2—C11—C12121.9 (3)
Cl4—Sn1—Cl294.22 (3)C20—C11—C12121.5 (3)
O1—Sn1—Cl1178.56 (7)C17—C12—C13117.9 (3)
N1—Sn1—Cl1103.94 (7)C17—C12—C11117.7 (3)
Cl4—Sn1—Cl190.53 (4)C13—C12—C11124.4 (3)
Cl2—Sn1—Cl192.77 (3)O2—C13—C14122.6 (3)
O1—Sn1—Cl390.14 (7)O2—C13—C12116.5 (3)
N1—Sn1—Cl384.93 (7)C14—C13—C12120.8 (3)
Cl4—Sn1—Cl3171.46 (3)C13—C14—C15120.0 (3)
Cl2—Sn1—Cl394.32 (3)C13—C14—H14120.0
Cl1—Sn1—Cl389.20 (4)C15—C14—H14120.0
C2—O1—Sn1116.63 (19)C16—C15—C14121.1 (3)
C13—O2—H2109 (3)C16—C15—H15119.5
C24—O3—H3105 (3)C14—C15—H15119.5
C25—O4—H4104 (4)C15—C16—C17120.2 (3)
C9—N1—C1119.5 (3)C15—C16—H16119.9
C9—N1—Sn1131.3 (2)C17—C16—H16119.9
C1—N1—Sn1109.2 (2)C16—C17—C12119.9 (3)
C23—N2—C11124.4 (3)C16—C17—C18120.7 (3)
C23—N2—H1110 (3)C12—C17—C18119.3 (3)
C11—N2—H1126 (3)C19—C18—C17121.8 (3)
N1—C1—C6122.7 (3)C19—C18—H18119.1
N1—C1—C2117.1 (3)C17—C18—H18119.1
C6—C1—C2120.3 (3)C18—C19—C20121.1 (3)
O1—C2—C3122.2 (3)C18—C19—H19119.4
O1—C2—C1119.5 (3)C20—C19—H19119.4
C3—C2—C1118.3 (3)C21—C20—C11119.3 (3)
C2—C3—C4120.8 (3)C21—C20—C19122.2 (3)
C2—C3—H3A119.6C11—C20—C19118.5 (3)
C4—C3—H3A119.6C22—C21—C20121.0 (4)
C5—C4—C3121.7 (3)C22—C21—H21119.5
C5—C4—H4A119.2C20—C21—H21119.5
C3—C4—H4A119.2C21—C22—C23118.2 (4)
C4—C5—C6119.3 (3)C21—C22—H22120.9
C4—C5—H5120.3C23—C22—H22120.9
C6—C5—H5120.3N2—C23—C22120.6 (4)
C1—C6—C5119.6 (3)N2—C23—H23119.7
C1—C6—C7116.4 (3)C22—C23—H23119.7
C5—C6—C7123.9 (3)O3—C24—H24A109.5
C8—C7—C6120.1 (3)O3—C24—H24B109.5
C8—C7—H7120.0H24A—C24—H24B109.5
C6—C7—H7120.0O3—C24—H24C109.5
C7—C8—C9120.8 (3)H24A—C24—H24C109.5
C7—C8—H8119.6H24B—C24—H24C109.5
C9—C8—H8119.6O4—C25—H25A109.5
N1—C9—C8120.5 (3)O4—C25—H25B109.5
N1—C9—C10119.5 (3)H25A—C25—H25B109.5
C8—C9—C10119.9 (3)O4—C25—H25C109.5
C9—C10—H10A109.5H25A—C25—H25C109.5
C9—C10—H10B109.5H25B—C25—H25C109.5
H10A—C10—H10B109.5
N1—Sn1—O1—C2−5.0 (2)C1—N1—C9—C10−178.0 (3)
Cl4—Sn1—O1—C2−91.7 (2)Sn1—N1—C9—C105.3 (5)
Cl2—Sn1—O1—C2174.1 (2)C7—C8—C9—N1−0.7 (6)
Cl3—Sn1—O1—C279.8 (2)C7—C8—C9—C10178.6 (4)
O1—Sn1—N1—C9−178.4 (3)C23—N2—C11—C200.3 (5)
Cl4—Sn1—N1—C9−87.4 (3)C23—N2—C11—C12179.5 (3)
Cl2—Sn1—N1—C9178.4 (2)N2—C11—C12—C17−179.2 (3)
Cl1—Sn1—N1—C92.4 (3)C20—C11—C12—C170.0 (5)
Cl3—Sn1—N1—C990.3 (3)N2—C11—C12—C130.6 (5)
O1—Sn1—N1—C14.6 (2)C20—C11—C12—C13179.8 (3)
Cl4—Sn1—N1—C195.7 (2)C17—C12—C13—O2−179.5 (3)
Cl2—Sn1—N1—C11.5 (4)C11—C12—C13—O20.7 (5)
Cl1—Sn1—N1—C1−174.57 (19)C17—C12—C13—C140.3 (5)
Cl3—Sn1—N1—C1−86.7 (2)C11—C12—C13—C14−179.4 (3)
C9—N1—C1—C6−0.7 (5)O2—C13—C14—C15−179.3 (3)
Sn1—N1—C1—C6176.6 (3)C12—C13—C14—C150.8 (5)
C9—N1—C1—C2178.8 (3)C13—C14—C15—C16−1.0 (5)
Sn1—N1—C1—C2−3.8 (3)C14—C15—C16—C170.0 (5)
Sn1—O1—C2—C3−175.9 (2)C15—C16—C17—C121.2 (5)
Sn1—O1—C2—C14.7 (4)C15—C16—C17—C18179.7 (3)
N1—C1—C2—O1−0.2 (4)C13—C12—C17—C16−1.3 (5)
C6—C1—C2—O1179.4 (3)C11—C12—C17—C16178.4 (3)
N1—C1—C2—C3−179.6 (3)C13—C12—C17—C18−179.9 (3)
C6—C1—C2—C30.0 (5)C11—C12—C17—C18−0.1 (5)
O1—C2—C3—C4−179.5 (3)C16—C17—C18—C19−179.2 (3)
C1—C2—C3—C4−0.2 (5)C12—C17—C18—C19−0.7 (5)
C2—C3—C4—C50.3 (5)C17—C18—C19—C201.5 (6)
C3—C4—C5—C6−0.3 (5)N2—C11—C20—C210.1 (5)
N1—C1—C6—C5179.5 (3)C12—C11—C20—C21−179.2 (3)
C2—C1—C6—C50.0 (5)N2—C11—C20—C19−179.9 (3)
N1—C1—C6—C7−0.5 (5)C12—C11—C20—C190.8 (5)
C2—C1—C6—C7180.0 (3)C18—C19—C20—C21178.4 (3)
C4—C5—C6—C10.2 (5)C18—C19—C20—C11−1.6 (5)
C4—C5—C6—C7−179.8 (3)C11—C20—C21—C22−0.6 (5)
C1—C6—C7—C81.2 (5)C19—C20—C21—C22179.4 (4)
C5—C6—C7—C8−178.9 (3)C20—C21—C22—C230.9 (6)
C6—C7—C8—C9−0.6 (5)C11—N2—C23—C220.0 (6)
C1—N1—C9—C81.3 (5)C21—C22—C23—N2−0.5 (6)
Sn1—N1—C9—C8−175.4 (2)
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.84 (1)1.75 (2)2.570 (3)164 (5)
O3—H3···O10.84 (1)1.94 (2)2.746 (3)162 (4)
N2—H1···O40.89 (1)2.09 (3)2.816 (4)138 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O2—H2⋯O30.84 (1)1.75 (2)2.570 (3)164 (5)
O3—H3⋯O10.84 (1)1.94 (2)2.746 (3)162 (4)
N2—H1⋯O40.89 (1)2.09 (3)2.816 (4)138 (3)
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  8-Hydr-oxy-2-methyl-quinolinium tetra-chlorido(quinolin-8-olato-κN,O)stannate(IV) acetonitrile monosolvate.

Authors:  Marzieh Vafaee; Gholamhossein Mohammadnezhad; Mostafa M Amini; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-06
  2 in total

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