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metal-organic compounds
10-Hydroxybenzo[h]quinolinium tetrachlorido(2-methylquinolin-8-olato-κ2N,O)stannate(IV) methanol disolvate
aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my
In the disolvated title salt, (C13H10NO)[SnCl4(C10H8NO)]·2CH3OH, the SnIV atom is chelated by the N,O-bidentate 2-methylquinolin-8-olate ion and is further coordinated by four chloride ions, showing a distorted octahedral SnNOCl4 geometry. In the crystal, the cation and anion are linked to the methanol molecules by O—H⋯O and N—H⋯O hydrogen bonds.
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
|
Refinement
|
|
Data collection: CrysAlis PRO (Agilent, 2010); cell 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
).
Supporting information
10.1107/S1600536811031461/xu5283sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811031461/xu5283Isup2.hkl
Stannic chloride pentahydrate (0.35 g, 1 mmol), 10-hydroxybenzo[h]quinoline (0.20 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Yellow crystals were collected from the side arm after several days (in approximately yield 80%, m.p. 538 K).
Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the
in the riding model approximation.The ammonium and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01, O–H 0.84±0.01 Å; their temperature factors were refined.
The final difference Fourier map had a peak as well as a hole in the vicinity ot Sn1.
Omitted from the
was the (0 0 2) reflection.Data collection: CrysAlis PRO (Agilent, 2010); cell
CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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). ![]() | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (C14H10NO)[SnCl4(C10H8NO)].2CH3OH, at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
(C13H10NO)[SnCl4(C10H8NO)]·2CH4O | Z = 2 |
Mr = 678.97 | F(000) = 680 |
Triclinic, P1 | Dx = 1.701 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5645 (2) Å | Cell parameters from 6565 reflections |
b = 10.1112 (3) Å | θ = 2.3–29.3° |
c = 17.7837 (5) Å | µ = 1.40 mm−1 |
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 detector | 5871 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 5239 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.056 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.5°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −10→12 |
Tmin = 0.678, Tmax = 0.873 | l = −22→23 |
10548 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0329P)2 + 1.5116P] where P = (Fo2 + 2Fc2)/3 |
5871 reflections | (Δ/σ)max = 0.001 |
340 parameters | Δρmax = 1.23 e Å−3 |
4 restraints | Δρmin = −1.14 e Å−3 |
(C13H10NO)[SnCl4(C10H8NO)]·2CH4O | γ = 97.509 (3)° |
Mr = 678.97 | V = 1325.56 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5645 (2) Å | Mo Kα radiation |
b = 10.1112 (3) Å | µ = 1.40 mm−1 |
c = 17.7837 (5) Å | T = 100 K |
α = 98.105 (3)° | 0.30 × 0.30 × 0.10 mm |
β = 95.653 (3)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5871 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 5239 reflections with I > 2σ(I) |
Tmin = 0.678, Tmax = 0.873 | Rint = 0.056 |
10548 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 4 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 1.23 e Å−3 |
5871 reflections | Δρmin = −1.14 e Å−3 |
340 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.86883 (3) | 0.09428 (2) | 0.789295 (13) | 0.01747 (8) | |
Cl1 | 0.86363 (16) | −0.14417 (9) | 0.78823 (6) | 0.0417 (3) | |
Cl2 | 0.63271 (12) | 0.06051 (9) | 0.68485 (5) | 0.02469 (19) | |
Cl3 | 0.66698 (12) | 0.09658 (10) | 0.88638 (5) | 0.0303 (2) | |
Cl4 | 1.10456 (13) | 0.09761 (11) | 0.70839 (5) | 0.0340 (2) | |
O1 | 0.8665 (3) | 0.2980 (2) | 0.78929 (13) | 0.0164 (5) | |
O2 | 0.3798 (4) | 0.4948 (3) | 0.64356 (15) | 0.0274 (6) | |
H2 | 0.453 (5) | 0.464 (4) | 0.672 (2) | 0.041* | |
O3 | 0.5605 (3) | 0.4044 (3) | 0.75020 (15) | 0.0261 (6) | |
H3 | 0.649 (4) | 0.363 (4) | 0.752 (3) | 0.039* | |
O4 | 0.4163 (4) | 0.7760 (3) | 0.73826 (19) | 0.0459 (8) | |
H4 | 0.507 (5) | 0.836 (4) | 0.749 (3) | 0.069* | |
N1 | 1.0833 (4) | 0.1902 (3) | 0.88721 (15) | 0.0165 (6) | |
N2 | 0.2612 (4) | 0.6931 (3) | 0.58555 (18) | 0.0226 (6) | |
H1 | 0.304 (5) | 0.673 (4) | 0.6302 (12) | 0.027* | |
C1 | 1.0870 (4) | 0.3279 (3) | 0.89787 (19) | 0.0164 (7) | |
C2 | 0.9706 (4) | 0.3813 (3) | 0.84513 (19) | 0.0165 (7) | |
C3 | 0.9725 (5) | 0.5190 (3) | 0.8541 (2) | 0.0210 (7) | |
H3A | 0.8964 | 0.5564 | 0.8197 | 0.025* | |
C4 | 1.0860 (5) | 0.6053 (4) | 0.9140 (2) | 0.0240 (8) | |
H4A | 1.0843 | 0.6999 | 0.9191 | 0.029* | |
C5 | 1.1982 (5) | 0.5561 (4) | 0.9646 (2) | 0.0229 (7) | |
H5 | 1.2740 | 0.6159 | 1.0043 | 0.028* | |
C6 | 1.2003 (4) | 0.4154 (3) | 0.95736 (19) | 0.0192 (7) | |
C7 | 1.3109 (5) | 0.3538 (4) | 1.0069 (2) | 0.0234 (8) | |
H7 | 1.3881 | 0.4078 | 1.0484 | 0.028* | |
C8 | 1.3067 (5) | 0.2178 (4) | 0.9950 (2) | 0.0254 (8) | |
H8 | 1.3821 | 0.1773 | 1.0281 | 0.031* | |
C9 | 1.1914 (5) | 0.1355 (4) | 0.9339 (2) | 0.0213 (7) | |
C10 | 1.1918 (6) | −0.0137 (4) | 0.9208 (2) | 0.0320 (9) | |
H10A | 1.2077 | −0.0433 | 0.8673 | 0.048* | |
H10B | 1.0775 | −0.0596 | 0.9321 | 0.048* | |
H10C | 1.2907 | −0.0360 | 0.9543 | 0.048* | |
C11 | 0.2292 (4) | 0.6061 (4) | 0.5177 (2) | 0.0189 (7) | |
C12 | 0.2715 (4) | 0.4711 (4) | 0.5116 (2) | 0.0202 (7) | |
C13 | 0.3479 (4) | 0.4138 (4) | 0.5739 (2) | 0.0215 (7) | |
C14 | 0.3861 (5) | 0.2837 (4) | 0.5632 (2) | 0.0245 (8) | |
H14 | 0.4354 | 0.2465 | 0.6053 | 0.029* | |
C15 | 0.3524 (5) | 0.2065 (4) | 0.4906 (2) | 0.0256 (8) | |
H15 | 0.3810 | 0.1171 | 0.4835 | 0.031* | |
C16 | 0.2783 (5) | 0.2574 (4) | 0.4289 (2) | 0.0256 (8) | |
H16 | 0.2563 | 0.2032 | 0.3798 | 0.031* | |
C17 | 0.2354 (4) | 0.3891 (4) | 0.4384 (2) | 0.0214 (7) | |
C18 | 0.1589 (5) | 0.4437 (4) | 0.3745 (2) | 0.0263 (8) | |
H18 | 0.1362 | 0.3889 | 0.3256 | 0.032* | |
C19 | 0.1186 (5) | 0.5699 (4) | 0.3819 (2) | 0.0262 (8) | |
H19 | 0.0654 | 0.6017 | 0.3385 | 0.031* | |
C20 | 0.1542 (4) | 0.6568 (4) | 0.4535 (2) | 0.0222 (7) | |
C21 | 0.1174 (5) | 0.7900 (4) | 0.4624 (2) | 0.0295 (9) | |
H21 | 0.0681 | 0.8246 | 0.4193 | 0.035* | |
C22 | 0.1518 (5) | 0.8716 (4) | 0.5327 (2) | 0.0288 (8) | |
H22 | 0.1253 | 0.9615 | 0.5388 | 0.035* | |
C23 | 0.2259 (5) | 0.8189 (4) | 0.5943 (2) | 0.0290 (8) | |
H23 | 0.2517 | 0.8735 | 0.6432 | 0.035* | |
C24 | 0.4551 (6) | 0.3602 (4) | 0.8063 (2) | 0.0329 (9) | |
H24A | 0.5270 | 0.3807 | 0.8566 | 0.049* | |
H24B | 0.4163 | 0.2626 | 0.7935 | 0.049* | |
H24C | 0.3496 | 0.4069 | 0.8075 | 0.049* | |
C25 | 0.4131 (7) | 0.7114 (5) | 0.8025 (2) | 0.0414 (10) | |
H25A | 0.5218 | 0.6691 | 0.8094 | 0.062* | |
H25B | 0.3070 | 0.6420 | 0.7955 | 0.062* | |
H25C | 0.4083 | 0.7777 | 0.8479 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02318 (13) | 0.01235 (12) | 0.01641 (13) | 0.00327 (9) | −0.00053 (9) | 0.00207 (8) |
Cl1 | 0.0566 (7) | 0.0134 (4) | 0.0472 (6) | 0.0041 (4) | −0.0256 (5) | 0.0014 (4) |
Cl2 | 0.0283 (4) | 0.0200 (4) | 0.0237 (4) | 0.0035 (3) | −0.0062 (4) | 0.0027 (3) |
Cl3 | 0.0279 (5) | 0.0373 (5) | 0.0282 (5) | −0.0008 (4) | 0.0084 (4) | 0.0156 (4) |
Cl4 | 0.0331 (5) | 0.0530 (6) | 0.0187 (4) | 0.0224 (5) | 0.0053 (4) | −0.0007 (4) |
O1 | 0.0193 (11) | 0.0139 (11) | 0.0167 (11) | 0.0049 (9) | 0.0023 (9) | 0.0027 (9) |
O2 | 0.0339 (15) | 0.0294 (15) | 0.0213 (14) | 0.0096 (12) | −0.0004 (12) | 0.0102 (11) |
O3 | 0.0230 (13) | 0.0351 (15) | 0.0266 (14) | 0.0133 (11) | 0.0089 (11) | 0.0143 (11) |
O4 | 0.0452 (18) | 0.049 (2) | 0.0390 (18) | −0.0141 (15) | −0.0075 (15) | 0.0209 (15) |
N1 | 0.0194 (13) | 0.0164 (14) | 0.0144 (14) | 0.0025 (11) | 0.0040 (11) | 0.0031 (11) |
N2 | 0.0192 (14) | 0.0256 (16) | 0.0242 (16) | 0.0015 (13) | 0.0018 (13) | 0.0104 (13) |
C1 | 0.0184 (15) | 0.0135 (15) | 0.0180 (16) | −0.0004 (13) | 0.0074 (13) | 0.0036 (12) |
C2 | 0.0167 (15) | 0.0177 (16) | 0.0167 (16) | 0.0029 (13) | 0.0083 (13) | 0.0039 (12) |
C3 | 0.0242 (17) | 0.0179 (17) | 0.0240 (18) | 0.0047 (14) | 0.0099 (15) | 0.0078 (14) |
C4 | 0.0272 (18) | 0.0135 (16) | 0.032 (2) | 0.0002 (14) | 0.0135 (16) | 0.0024 (14) |
C5 | 0.0218 (17) | 0.0196 (18) | 0.0244 (19) | −0.0027 (14) | 0.0071 (15) | −0.0042 (14) |
C6 | 0.0171 (16) | 0.0209 (17) | 0.0186 (17) | −0.0020 (13) | 0.0088 (14) | −0.0001 (13) |
C7 | 0.0196 (17) | 0.029 (2) | 0.0192 (18) | 0.0016 (15) | 0.0024 (14) | −0.0036 (14) |
C8 | 0.0246 (18) | 0.029 (2) | 0.0218 (18) | 0.0049 (16) | −0.0029 (15) | 0.0050 (15) |
C9 | 0.0249 (17) | 0.0204 (18) | 0.0192 (17) | 0.0047 (14) | 0.0020 (14) | 0.0047 (13) |
C10 | 0.040 (2) | 0.0217 (19) | 0.032 (2) | 0.0077 (17) | −0.0115 (18) | 0.0049 (16) |
C11 | 0.0128 (15) | 0.0243 (18) | 0.0214 (18) | 0.0013 (13) | 0.0046 (13) | 0.0090 (14) |
C12 | 0.0129 (15) | 0.0285 (19) | 0.0222 (18) | 0.0034 (14) | 0.0064 (14) | 0.0109 (14) |
C13 | 0.0182 (16) | 0.0268 (19) | 0.0217 (18) | 0.0034 (14) | 0.0051 (14) | 0.0089 (14) |
C14 | 0.0200 (17) | 0.029 (2) | 0.029 (2) | 0.0058 (15) | 0.0065 (15) | 0.0139 (15) |
C15 | 0.0227 (18) | 0.0247 (19) | 0.033 (2) | 0.0053 (15) | 0.0108 (16) | 0.0089 (15) |
C16 | 0.0238 (18) | 0.031 (2) | 0.0235 (19) | 0.0039 (16) | 0.0095 (15) | 0.0048 (15) |
C17 | 0.0166 (16) | 0.0291 (19) | 0.0215 (18) | 0.0039 (14) | 0.0079 (14) | 0.0100 (14) |
C18 | 0.0283 (19) | 0.036 (2) | 0.0170 (17) | 0.0049 (16) | 0.0064 (15) | 0.0081 (15) |
C19 | 0.0215 (17) | 0.040 (2) | 0.0220 (19) | 0.0068 (16) | 0.0067 (15) | 0.0156 (16) |
C20 | 0.0170 (16) | 0.030 (2) | 0.0236 (18) | 0.0041 (14) | 0.0071 (14) | 0.0135 (15) |
C21 | 0.0214 (18) | 0.038 (2) | 0.035 (2) | 0.0083 (17) | 0.0081 (17) | 0.0216 (18) |
C22 | 0.0288 (19) | 0.027 (2) | 0.034 (2) | 0.0071 (16) | 0.0080 (17) | 0.0113 (16) |
C23 | 0.0278 (19) | 0.024 (2) | 0.036 (2) | 0.0037 (16) | 0.0039 (17) | 0.0075 (16) |
C24 | 0.037 (2) | 0.034 (2) | 0.034 (2) | 0.0086 (18) | 0.0181 (18) | 0.0113 (17) |
C25 | 0.055 (3) | 0.037 (2) | 0.033 (2) | 0.006 (2) | 0.009 (2) | 0.0052 (19) |
Sn1—O1 | 2.063 (2) | C9—C10 | 1.494 (5) |
Sn1—N1 | 2.272 (3) | C10—H10A | 0.9800 |
Sn1—Cl4 | 2.3988 (10) | C10—H10B | 0.9800 |
Sn1—Cl2 | 2.4011 (8) | C10—H10C | 0.9800 |
Sn1—Cl1 | 2.4036 (9) | C11—C20 | 1.414 (5) |
Sn1—Cl3 | 2.4145 (9) | C11—C12 | 1.435 (5) |
O1—C2 | 1.324 (4) | C12—C17 | 1.422 (5) |
O2—C13 | 1.366 (4) | C12—C13 | 1.429 (5) |
O2—H2 | 0.843 (10) | C13—C14 | 1.375 (5) |
O3—C24 | 1.421 (5) | C14—C15 | 1.393 (5) |
O3—H3 | 0.835 (10) | C14—H14 | 0.9500 |
O4—C25 | 1.395 (5) | C15—C16 | 1.376 (5) |
O4—H4 | 0.838 (10) | C15—H15 | 0.9500 |
N1—C9 | 1.333 (4) | C16—C17 | 1.403 (5) |
N1—C1 | 1.374 (4) | C16—H16 | 0.9500 |
N2—C23 | 1.325 (5) | C17—C18 | 1.436 (5) |
N2—C11 | 1.369 (5) | C18—C19 | 1.342 (5) |
N2—H1 | 0.888 (10) | C18—H18 | 0.9500 |
C1—C6 | 1.413 (5) | C19—C20 | 1.423 (5) |
C1—C2 | 1.433 (5) | C19—H19 | 0.9500 |
C2—C3 | 1.377 (5) | C20—C21 | 1.401 (5) |
C3—C4 | 1.412 (5) | C21—C22 | 1.380 (6) |
C3—H3A | 0.9500 | C21—H21 | 0.9500 |
C4—C5 | 1.366 (5) | C22—C23 | 1.385 (5) |
C4—H4A | 0.9500 | C22—H22 | 0.9500 |
C5—C6 | 1.413 (5) | C23—H23 | 0.9500 |
C5—H5 | 0.9500 | C24—H24A | 0.9800 |
C6—C7 | 1.418 (5) | C24—H24B | 0.9800 |
C7—C8 | 1.358 (5) | C24—H24C | 0.9800 |
C7—H7 | 0.9500 | C25—H25A | 0.9800 |
C8—C9 | 1.415 (5) | C25—H25B | 0.9800 |
C8—H8 | 0.9500 | C25—H25C | 0.9800 |
O1—Sn1—N1 | 77.28 (9) | C9—C10—H10C | 109.5 |
O1—Sn1—Cl4 | 90.31 (7) | H10A—C10—H10C | 109.5 |
N1—Sn1—Cl4 | 86.85 (7) | H10B—C10—H10C | 109.5 |
O1—Sn1—Cl2 | 86.01 (6) | N2—C11—C20 | 116.6 (3) |
N1—Sn1—Cl2 | 163.26 (7) | N2—C11—C12 | 121.9 (3) |
Cl4—Sn1—Cl2 | 94.22 (3) | C20—C11—C12 | 121.5 (3) |
O1—Sn1—Cl1 | 178.56 (7) | C17—C12—C13 | 117.9 (3) |
N1—Sn1—Cl1 | 103.94 (7) | C17—C12—C11 | 117.7 (3) |
Cl4—Sn1—Cl1 | 90.53 (4) | C13—C12—C11 | 124.4 (3) |
Cl2—Sn1—Cl1 | 92.77 (3) | O2—C13—C14 | 122.6 (3) |
O1—Sn1—Cl3 | 90.14 (7) | O2—C13—C12 | 116.5 (3) |
N1—Sn1—Cl3 | 84.93 (7) | C14—C13—C12 | 120.8 (3) |
Cl4—Sn1—Cl3 | 171.46 (3) | C13—C14—C15 | 120.0 (3) |
Cl2—Sn1—Cl3 | 94.32 (3) | C13—C14—H14 | 120.0 |
Cl1—Sn1—Cl3 | 89.20 (4) | C15—C14—H14 | 120.0 |
C2—O1—Sn1 | 116.63 (19) | C16—C15—C14 | 121.1 (3) |
C13—O2—H2 | 109 (3) | C16—C15—H15 | 119.5 |
C24—O3—H3 | 105 (3) | C14—C15—H15 | 119.5 |
C25—O4—H4 | 104 (4) | C15—C16—C17 | 120.2 (3) |
C9—N1—C1 | 119.5 (3) | C15—C16—H16 | 119.9 |
C9—N1—Sn1 | 131.3 (2) | C17—C16—H16 | 119.9 |
C1—N1—Sn1 | 109.2 (2) | C16—C17—C12 | 119.9 (3) |
C23—N2—C11 | 124.4 (3) | C16—C17—C18 | 120.7 (3) |
C23—N2—H1 | 110 (3) | C12—C17—C18 | 119.3 (3) |
C11—N2—H1 | 126 (3) | C19—C18—C17 | 121.8 (3) |
N1—C1—C6 | 122.7 (3) | C19—C18—H18 | 119.1 |
N1—C1—C2 | 117.1 (3) | C17—C18—H18 | 119.1 |
C6—C1—C2 | 120.3 (3) | C18—C19—C20 | 121.1 (3) |
O1—C2—C3 | 122.2 (3) | C18—C19—H19 | 119.4 |
O1—C2—C1 | 119.5 (3) | C20—C19—H19 | 119.4 |
C3—C2—C1 | 118.3 (3) | C21—C20—C11 | 119.3 (3) |
C2—C3—C4 | 120.8 (3) | C21—C20—C19 | 122.2 (3) |
C2—C3—H3A | 119.6 | C11—C20—C19 | 118.5 (3) |
C4—C3—H3A | 119.6 | C22—C21—C20 | 121.0 (4) |
C5—C4—C3 | 121.7 (3) | C22—C21—H21 | 119.5 |
C5—C4—H4A | 119.2 | C20—C21—H21 | 119.5 |
C3—C4—H4A | 119.2 | C21—C22—C23 | 118.2 (4) |
C4—C5—C6 | 119.3 (3) | C21—C22—H22 | 120.9 |
C4—C5—H5 | 120.3 | C23—C22—H22 | 120.9 |
C6—C5—H5 | 120.3 | N2—C23—C22 | 120.6 (4) |
C1—C6—C5 | 119.6 (3) | N2—C23—H23 | 119.7 |
C1—C6—C7 | 116.4 (3) | C22—C23—H23 | 119.7 |
C5—C6—C7 | 123.9 (3) | O3—C24—H24A | 109.5 |
C8—C7—C6 | 120.1 (3) | O3—C24—H24B | 109.5 |
C8—C7—H7 | 120.0 | H24A—C24—H24B | 109.5 |
C6—C7—H7 | 120.0 | O3—C24—H24C | 109.5 |
C7—C8—C9 | 120.8 (3) | H24A—C24—H24C | 109.5 |
C7—C8—H8 | 119.6 | H24B—C24—H24C | 109.5 |
C9—C8—H8 | 119.6 | O4—C25—H25A | 109.5 |
N1—C9—C8 | 120.5 (3) | O4—C25—H25B | 109.5 |
N1—C9—C10 | 119.5 (3) | H25A—C25—H25B | 109.5 |
C8—C9—C10 | 119.9 (3) | O4—C25—H25C | 109.5 |
C9—C10—H10A | 109.5 | H25A—C25—H25C | 109.5 |
C9—C10—H10B | 109.5 | H25B—C25—H25C | 109.5 |
H10A—C10—H10B | 109.5 | ||
N1—Sn1—O1—C2 | −5.0 (2) | C1—N1—C9—C10 | −178.0 (3) |
Cl4—Sn1—O1—C2 | −91.7 (2) | Sn1—N1—C9—C10 | 5.3 (5) |
Cl2—Sn1—O1—C2 | 174.1 (2) | C7—C8—C9—N1 | −0.7 (6) |
Cl3—Sn1—O1—C2 | 79.8 (2) | C7—C8—C9—C10 | 178.6 (4) |
O1—Sn1—N1—C9 | −178.4 (3) | C23—N2—C11—C20 | 0.3 (5) |
Cl4—Sn1—N1—C9 | −87.4 (3) | C23—N2—C11—C12 | 179.5 (3) |
Cl2—Sn1—N1—C9 | 178.4 (2) | N2—C11—C12—C17 | −179.2 (3) |
Cl1—Sn1—N1—C9 | 2.4 (3) | C20—C11—C12—C17 | 0.0 (5) |
Cl3—Sn1—N1—C9 | 90.3 (3) | N2—C11—C12—C13 | 0.6 (5) |
O1—Sn1—N1—C1 | 4.6 (2) | C20—C11—C12—C13 | 179.8 (3) |
Cl4—Sn1—N1—C1 | 95.7 (2) | C17—C12—C13—O2 | −179.5 (3) |
Cl2—Sn1—N1—C1 | 1.5 (4) | C11—C12—C13—O2 | 0.7 (5) |
Cl1—Sn1—N1—C1 | −174.57 (19) | C17—C12—C13—C14 | 0.3 (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—C6 | 176.6 (3) | C12—C13—C14—C15 | 0.8 (5) |
C9—N1—C1—C2 | 178.8 (3) | C13—C14—C15—C16 | −1.0 (5) |
Sn1—N1—C1—C2 | −3.8 (3) | C14—C15—C16—C17 | 0.0 (5) |
Sn1—O1—C2—C3 | −175.9 (2) | C15—C16—C17—C12 | 1.2 (5) |
Sn1—O1—C2—C1 | 4.7 (4) | C15—C16—C17—C18 | 179.7 (3) |
N1—C1—C2—O1 | −0.2 (4) | C13—C12—C17—C16 | −1.3 (5) |
C6—C1—C2—O1 | 179.4 (3) | C11—C12—C17—C16 | 178.4 (3) |
N1—C1—C2—C3 | −179.6 (3) | C13—C12—C17—C18 | −179.9 (3) |
C6—C1—C2—C3 | 0.0 (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—C5 | 0.3 (5) | C17—C18—C19—C20 | 1.5 (6) |
C3—C4—C5—C6 | −0.3 (5) | N2—C11—C20—C21 | 0.1 (5) |
N1—C1—C6—C5 | 179.5 (3) | C12—C11—C20—C21 | −179.2 (3) |
C2—C1—C6—C5 | 0.0 (5) | N2—C11—C20—C19 | −179.9 (3) |
N1—C1—C6—C7 | −0.5 (5) | C12—C11—C20—C19 | 0.8 (5) |
C2—C1—C6—C7 | 180.0 (3) | C18—C19—C20—C21 | 178.4 (3) |
C4—C5—C6—C1 | 0.2 (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—C8 | 1.2 (5) | C19—C20—C21—C22 | 179.4 (4) |
C5—C6—C7—C8 | −178.9 (3) | C20—C21—C22—C23 | 0.9 (6) |
C6—C7—C8—C9 | −0.6 (5) | C11—N2—C23—C22 | 0.0 (6) |
C1—N1—C9—C8 | 1.3 (5) | C21—C22—C23—N2 | −0.5 (6) |
Sn1—N1—C9—C8 | −175.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 (1) | 1.75 (2) | 2.570 (3) | 164 (5) |
O3—H3···O1 | 0.84 (1) | 1.94 (2) | 2.746 (3) | 162 (4) |
N2—H1···O4 | 0.89 (1) | 2.09 (3) | 2.816 (4) | 138 (3) |
Experimental details
Crystal data | |
Chemical formula | (C13H10NO)[SnCl4(C10H8NO)]·2CH4O |
Mr | 678.97 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.5645 (2), 10.1112 (3), 17.7837 (5) |
α, β, γ (°) | 98.105 (3), 95.653 (3), 97.509 (3) |
V (Å3) | 1325.56 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.30 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.678, 0.873 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10548, 5871, 5239 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.095, 1.11 |
No. of reflections | 5871 |
No. of parameters | 340 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.23, −1.14 |
Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 (1) | 1.75 (2) | 2.570 (3) | 164 (5) |
O3—H3···O1 | 0.84 (1) | 1.94 (2) | 2.746 (3) | 162 (4) |
N2—H1···O4 | 0.89 (1) | 2.09 (3) | 2.816 (4) | 138 (3) |
Acknowledgements
We thank Shahid Beheshti University and the University of Malaya for supporting this study.
References
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vafaee, M., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m381–m382. CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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We have been attempting to synthesize mixed-chelate tin(IV) compounds; in a recent study, we reacted stannic chloride with 8-hydroxyquinoline and 2-methyl-8-hydroxyquinoline (Vafaee et al., 2010). However, the reaction yielded 2-methyl-8-hydroxyquinolinium tetrachlorido(quinolin-8-olato)stannate as an acetonitrile solvate. The ligand that enages in coordination is the one that is less sterically crowded. A similar synthesis but with 10-hydroxybenzo[h]quinoline and 2-methyl-8-hydroxyquinoline in methanol medium yielded the di-solvated title salt (Scheme I, Fig. 1). Similarly, the less sterically crowded ligand engages in chelation, so that the more crowded ligand is now protonated. The SnIV atom shows octahedral SnNOCl4 coordination. The cation and anion are linked to the methanol molecules by O–H···O and N–H···O hydrogen bonds. One of the solvent molecules functions only as acceptor whereas the other functions both as a donor as well as acceptor.