10-Hy­droxy­benzo[h]quinolinium tetra­chlorido(2-methyl­quinolin-8-olato-κ2N,O)stannate(IV) methanol disolvate

Najafi, E.; Vafaee, M.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536811031461

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1223

doi:10.1107/S1600536811031461

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10-Hydroxybenzo[h]quinolinium tetrachlorido(2-methylquinolin-8-olato-κ²N,O)stannate(IV) methanol disolvate

Ezzatollah Najafi,^a Marzieh Vafaee,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^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

(Received 1 August 2011; accepted 4 August 2011; online 11 August 2011)

In the disolvated title salt, (C₁₃H₁₀NO)[SnCl₄(C₁₀H₈NO)]·2CH₃OH, the Sn^IV 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

(C₁₃H₁₀NO)[SnCl₄(C₁₀H₈NO)]·2CH₄O
M_r = 678.97
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.095
S = 1.11
5871 reflections
340 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.23 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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)

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031461/xu5283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031461/xu5283Isup2.hkl

checkCIF report

Comment top

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 Sn^IV 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.

Related literature top

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

Experimental top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: 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).

Figures top

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.

10-Hydroxybenzo[h]quinolinium tetrachlorido(2-methylquinolin-8-olato-κ²N,O)stannate(IV) methanol disolvate top

Crystal data top

(C₁₃H₁₀NO)[SnCl₄(C₁₀H₈NO)]·2CH₄O	Z = 2
M_r = 678.97	F(000) = 680
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.056
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→12
T_min = 0.678, T_max = 0.873	l = −22→23
10548 measured reflections

Refinement top

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(F_o²) + (0.0329P)² + 1.5116P] where P = (F_o² + 2F_c²)/3
5871 reflections	(Δ/σ)_max = 0.001
340 parameters	Δρ_max = 1.23 e Å⁻³
4 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

(C₁₃H₁₀NO)[SnCl₄(C₁₀H₈NO)]·2CH₄O	γ = 97.509 (3)°
M_r = 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)°

Data collection top

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)
T_min = 0.678, T_max = 0.873	R_int = 0.056
10548 measured reflections

Refinement top

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	Δρ_max = 1.23 e Å⁻³
5871 reflections	Δρ_min = −1.14 e Å⁻³
340 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.678, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	10548, 5871, 5239
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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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