8-Hy­droxy-2-methyl­quinolinium tetra­chlorido(quinolin-8-olato-κ2N,O)stan­nate(IV)

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

doi:10.1107/S1600536812019459

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m738

doi:10.1107/S1600536812019459

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8-Hydroxy-2-methylquinolinium tetrachlorido(quinolin-8-olato-κ²N,O)stannate(IV)

Ezzatollah Najafi,^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 30 April 2012; accepted 30 April 2012; online 5 May 2012)

The reaction of 8-hydroxyquinoline, 2-methylquinolin-8-ol and stannic chloride yields the protonated 8-hydroxy-2-methylquinolinium species. In the title salt, (C₁₀H₁₀NO)[Sn(C₉H₆NO)Cl₄], the Sn^IV cation is N,O-chelated by the quinolin-8-olate anion and is further coordinated by four Cl⁻ anions in a distorted cis-SnNOCl₄ octahedral geometry. In the crystal, the cation is linked to the anion by an O—H⋯O hydrogen bond.

Related literature

For the methanol solvate of the salt, see: Najafi et al. (2011 ).

Experimental

Crystal data

(C₁₀H₁₀NO)[Sn(C₉H₆NO)Cl₄]
M_r = 564.83
Monoclinic, P 2₁ /c
a = 8.9431 (3) Å
b = 11.5892 (4) Å
c = 20.1795 (8) Å
β = 101.347 (4)°
V = 2050.59 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.79 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.616, T_max = 0.717
13674 measured reflections
4723 independent reflections
4222 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.055
S = 1.06
4723 reflections
262 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1	0.84 (1)	1.86 (1)	2.683 (2)	168 (3)

Data collection: CrysAlis PRO (Agilent, 2012); 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/S1600536812019459/xu5531sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019459/xu5531Isup2.hkl

checkCIF report

Comment top

The reaction of 8-hydroxyquinoline, 2-methyl-8-hydroxyquinoline and stannic chloride in methanol yields a protonated 2-methyl-8-hydroxyquinoline species. The Sn^IVatom in the methanol-solvated salt, (C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]^.2CH₃OH, is N,O-chelated by the quinolin-8-olate (Najafi et al., 2011). A repeat of the synthesis but isopropyl alcohol in place of methanol yielded the unsolvated salt (Scheme I). The Sn^IVatom in the salt is N,O-chelated by the quinolin-8-olate in a cis-SnNOCl₄ octahedral geometry. The cation is linked to the anion by an O–H···O hydrogen bond (Fig. 1, Table 1).

Related literature top

For the methanol solvate of the salt, see: Najafi et al. (2011).

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol), 8-hydroxyquinoline (0.15 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube; the tube was filled with dry isopropyl alcohol and kept at 333 K. Yellow crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

8-Hydroxy-2-methylquinolinium tetrachlorido(quinolin-8-olato-κ²N,O)stannate(IV) top

Crystal data top

(C₁₀H₁₀NO)[Sn(C₉H₆NO)Cl₄]	F(000) = 1112
M_r = 564.83	D_x = 1.830 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6840 reflections
a = 8.9431 (3) Å	θ = 2.3–27.5°
b = 11.5892 (4) Å	µ = 1.79 mm⁻¹
c = 20.1795 (8) Å	T = 100 K
β = 101.347 (4)°	Prism, yellow
V = 2050.59 (13) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4723 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4222 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −14→15
T_min = 0.616, T_max = 0.717	l = −17→26
13674 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.055	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0193P)² + 1.171P] where P = (F_o² + 2F_c²)/3
4723 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.48 e Å⁻³
2 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[Sn(C₉H₆NO)Cl₄]	V = 2050.59 (13) Å³
M_r = 564.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9431 (3) Å	µ = 1.79 mm⁻¹
b = 11.5892 (4) Å	T = 100 K
c = 20.1795 (8) Å	0.30 × 0.25 × 0.20 mm
β = 101.347 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4723 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	4222 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.717	R_int = 0.029
13674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	2 restraints
wR(F²) = 0.055	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.48 e Å⁻³
4723 reflections	Δρ_min = −0.54 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.252394 (17)	0.454836 (13)	0.684298 (7)	0.01219 (5)
Cl1	0.06888 (7)	0.32750 (5)	0.71370 (3)	0.01978 (13)
Cl2	0.36818 (7)	0.51365 (5)	0.79638 (3)	0.01813 (12)
Cl3	0.43713 (6)	0.30303 (5)	0.68659 (3)	0.01751 (12)
Cl4	0.07496 (7)	0.61568 (5)	0.67319 (3)	0.01740 (12)
O1	0.17767 (18)	0.42497 (13)	0.58138 (8)	0.0149 (3)
O2	0.0249 (2)	0.25623 (14)	0.50577 (9)	0.0221 (4)
N1	0.4033 (2)	0.56783 (15)	0.63929 (10)	0.0141 (4)
N2	−0.0535 (2)	0.12664 (17)	0.39515 (10)	0.0161 (4)
C1	0.5172 (3)	0.6332 (2)	0.66989 (12)	0.0188 (5)
H1A	0.5461	0.6301	0.7177	0.023*
C2	0.5963 (3)	0.7065 (2)	0.63406 (13)	0.0224 (6)
H2A	0.6782	0.7523	0.6572	0.027*
C3	0.5545 (3)	0.7115 (2)	0.56511 (13)	0.0227 (5)
H3	0.6070	0.7618	0.5403	0.027*
C4	0.4339 (3)	0.6427 (2)	0.53060 (12)	0.0186 (5)
C5	0.3821 (3)	0.6417 (2)	0.45981 (13)	0.0228 (6)
H5	0.4297	0.6892	0.4316	0.027*
C6	0.2630 (3)	0.5720 (2)	0.43221 (12)	0.0227 (6)
H6	0.2276	0.5730	0.3846	0.027*
C7	0.1908 (3)	0.4985 (2)	0.47190 (12)	0.0187 (5)
H7	0.1084	0.4511	0.4509	0.022*
C8	0.2391 (3)	0.4952 (2)	0.54069 (11)	0.0145 (5)
C9	0.3609 (3)	0.56980 (19)	0.57047 (11)	0.0147 (5)
C10	−0.2450 (3)	0.1085 (2)	0.29236 (13)	0.0254 (6)
H10A	−0.2408	0.1929	0.2898	0.038*
H10B	−0.3371	0.0854	0.3084	0.038*
H10C	−0.2472	0.0756	0.2474	0.038*
C11	−0.1082 (3)	0.0656 (2)	0.34005 (12)	0.0178 (5)
C12	−0.0360 (3)	−0.0387 (2)	0.33034 (12)	0.0197 (5)
H12	−0.0737	−0.0843	0.2915	0.024*
C13	0.0878 (3)	−0.0750 (2)	0.37615 (12)	0.0193 (5)
H13	0.1363	−0.1454	0.3687	0.023*
C14	0.1453 (3)	−0.0089 (2)	0.43484 (12)	0.0176 (5)
C15	0.2728 (3)	−0.0407 (2)	0.48462 (13)	0.0215 (5)
H15	0.3271	−0.1096	0.4797	0.026*
C16	0.3176 (3)	0.0281 (2)	0.53985 (13)	0.0227 (6)
H16	0.4045	0.0069	0.5728	0.027*
C17	0.2382 (3)	0.1294 (2)	0.54906 (12)	0.0198 (5)
H17	0.2709	0.1751	0.5883	0.024*
C18	0.1135 (3)	0.1629 (2)	0.50175 (12)	0.0169 (5)
C19	0.0689 (3)	0.0939 (2)	0.44380 (11)	0.0153 (5)
H1	0.071 (3)	0.303 (2)	0.5341 (12)	0.036 (9)*
H2	−0.099 (3)	0.1922 (13)	0.4000 (13)	0.020 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01472 (9)	0.01041 (8)	0.01115 (8)	−0.00037 (6)	0.00186 (6)	−0.00024 (6)
Cl1	0.0212 (3)	0.0150 (3)	0.0243 (3)	−0.0044 (2)	0.0074 (2)	0.0002 (2)
Cl2	0.0193 (3)	0.0214 (3)	0.0131 (3)	−0.0001 (2)	0.0016 (2)	−0.0029 (2)
Cl3	0.0196 (3)	0.0159 (3)	0.0163 (3)	0.0045 (2)	0.0019 (2)	−0.0001 (2)
Cl4	0.0208 (3)	0.0137 (3)	0.0176 (3)	0.0038 (2)	0.0036 (2)	0.0006 (2)
O1	0.0173 (8)	0.0144 (8)	0.0127 (8)	−0.0002 (7)	0.0025 (6)	−0.0007 (6)
O2	0.0236 (9)	0.0169 (9)	0.0246 (10)	−0.0012 (8)	0.0018 (8)	−0.0085 (7)
N1	0.0170 (10)	0.0106 (9)	0.0152 (10)	0.0006 (8)	0.0046 (8)	−0.0003 (7)
N2	0.0163 (10)	0.0128 (10)	0.0194 (10)	0.0002 (8)	0.0039 (8)	−0.0004 (8)
C1	0.0201 (12)	0.0167 (12)	0.0197 (12)	−0.0029 (10)	0.0043 (10)	−0.0036 (10)
C2	0.0200 (12)	0.0164 (12)	0.0318 (15)	−0.0059 (10)	0.0075 (11)	−0.0050 (10)
C3	0.0224 (13)	0.0179 (12)	0.0321 (15)	−0.0005 (11)	0.0156 (11)	0.0025 (11)
C4	0.0205 (12)	0.0149 (11)	0.0225 (13)	0.0066 (10)	0.0092 (10)	0.0022 (10)
C5	0.0290 (14)	0.0208 (13)	0.0220 (13)	0.0088 (11)	0.0131 (11)	0.0060 (10)
C6	0.0294 (14)	0.0257 (14)	0.0135 (12)	0.0127 (12)	0.0056 (10)	0.0026 (10)
C7	0.0181 (12)	0.0202 (12)	0.0166 (12)	0.0051 (10)	0.0003 (9)	−0.0013 (10)
C8	0.0159 (11)	0.0118 (10)	0.0162 (11)	0.0050 (9)	0.0041 (9)	0.0008 (9)
C9	0.0168 (11)	0.0120 (11)	0.0158 (11)	0.0061 (9)	0.0047 (9)	0.0017 (9)
C10	0.0208 (13)	0.0287 (15)	0.0239 (14)	−0.0040 (11)	−0.0022 (11)	−0.0005 (11)
C11	0.0174 (12)	0.0183 (12)	0.0181 (12)	−0.0069 (10)	0.0044 (10)	0.0001 (9)
C12	0.0251 (13)	0.0186 (12)	0.0176 (12)	−0.0066 (11)	0.0098 (10)	−0.0050 (9)
C13	0.0238 (13)	0.0143 (11)	0.0219 (13)	−0.0006 (10)	0.0096 (10)	−0.0012 (10)
C14	0.0201 (12)	0.0163 (11)	0.0182 (12)	−0.0028 (10)	0.0083 (10)	0.0014 (9)
C15	0.0211 (13)	0.0201 (13)	0.0243 (13)	0.0026 (11)	0.0066 (11)	0.0048 (10)
C16	0.0194 (12)	0.0278 (14)	0.0198 (13)	−0.0032 (11)	0.0008 (10)	0.0061 (11)
C17	0.0214 (12)	0.0226 (13)	0.0154 (12)	−0.0093 (11)	0.0036 (10)	−0.0012 (10)
C18	0.0183 (12)	0.0144 (11)	0.0188 (12)	−0.0056 (10)	0.0061 (9)	−0.0007 (9)
C19	0.0145 (11)	0.0171 (11)	0.0152 (11)	−0.0047 (10)	0.0052 (9)	0.0016 (9)

Geometric parameters (Å, º) top

Sn1—O1	2.0818 (15)	C6—C7	1.409 (4)
Sn1—N1	2.201 (2)	C6—H6	0.9500
Sn1—Cl1	2.3678 (6)	C7—C8	1.371 (3)
Sn1—Cl2	2.3938 (6)	C7—H7	0.9500
Sn1—Cl3	2.4076 (6)	C8—C9	1.427 (3)
Sn1—Cl4	2.4296 (6)	C10—C11	1.486 (3)
O1—C8	1.348 (3)	C10—H10A	0.9800
O2—C18	1.353 (3)	C10—H10B	0.9800
O2—H1	0.835 (10)	C10—H10C	0.9800
N1—C1	1.321 (3)	C11—C12	1.402 (3)
N1—C9	1.366 (3)	C12—C13	1.362 (3)
N2—C11	1.328 (3)	C12—H12	0.9500
N2—C19	1.372 (3)	C13—C14	1.419 (3)
N2—H2	0.878 (10)	C13—H13	0.9500
C1—C2	1.395 (3)	C14—C19	1.402 (3)
C1—H1A	0.9500	C14—C15	1.412 (3)
C2—C3	1.369 (4)	C15—C16	1.364 (4)
C2—H2A	0.9500	C15—H15	0.9500
C3—C4	1.411 (3)	C16—C17	1.404 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C9	1.411 (3)	C17—C18	1.373 (3)
C4—C5	1.412 (3)	C17—H17	0.9500
C5—C6	1.365 (4)	C18—C19	1.408 (3)
C5—H5	0.9500

O1—Sn1—N1	77.86 (7)	C8—C7—H7	119.9
O1—Sn1—Cl1	92.52 (5)	C6—C7—H7	119.9
N1—Sn1—Cl1	170.33 (5)	O1—C8—C7	123.2 (2)
O1—Sn1—Cl2	169.80 (5)	O1—C8—C9	118.6 (2)
N1—Sn1—Cl2	91.96 (5)	C7—C8—C9	118.2 (2)
Cl1—Sn1—Cl2	97.65 (2)	N1—C9—C4	121.5 (2)
O1—Sn1—Cl3	88.97 (5)	N1—C9—C8	117.0 (2)
N1—Sn1—Cl3	88.20 (5)	C4—C9—C8	121.5 (2)
Cl1—Sn1—Cl3	92.67 (2)	C11—C10—H10A	109.5
Cl2—Sn1—Cl3	91.28 (2)	C11—C10—H10B	109.5
O1—Sn1—Cl4	87.70 (4)	H10A—C10—H10B	109.5
N1—Sn1—Cl4	87.00 (5)	C11—C10—H10C	109.5
Cl1—Sn1—Cl4	91.66 (2)	H10A—C10—H10C	109.5
Cl2—Sn1—Cl4	91.26 (2)	H10B—C10—H10C	109.5
Cl3—Sn1—Cl4	174.65 (2)	N2—C11—C12	118.2 (2)
C8—O1—Sn1	114.70 (13)	N2—C11—C10	119.0 (2)
C18—O2—H1	110 (2)	C12—C11—C10	122.8 (2)
C1—N1—C9	120.0 (2)	C13—C12—C11	120.5 (2)
C1—N1—Sn1	128.84 (16)	C13—C12—H12	119.8
C9—N1—Sn1	111.09 (14)	C11—C12—H12	119.8
C11—N2—C19	124.2 (2)	C12—C13—C14	120.8 (2)
C11—N2—H2	116.8 (16)	C12—C13—H13	119.6
C19—N2—H2	119.0 (17)	C14—C13—H13	119.6
N1—C1—C2	122.0 (2)	C19—C14—C15	118.4 (2)
N1—C1—H1A	119.0	C19—C14—C13	117.4 (2)
C2—C1—H1A	119.0	C15—C14—C13	124.2 (2)
C3—C2—C1	119.2 (2)	C16—C15—C14	119.7 (2)
C3—C2—H2A	120.4	C16—C15—H15	120.2
C1—C2—H2A	120.4	C14—C15—H15	120.2
C2—C3—C4	120.5 (2)	C15—C16—C17	121.4 (2)
C2—C3—H3	119.8	C15—C16—H16	119.3
C4—C3—H3	119.8	C17—C16—H16	119.3
C3—C4—C9	116.8 (2)	C18—C17—C16	120.5 (2)
C3—C4—C5	124.8 (2)	C18—C17—H17	119.8
C9—C4—C5	118.4 (2)	C16—C17—H17	119.8
C6—C5—C4	119.4 (2)	O2—C18—C17	126.1 (2)
C6—C5—H5	120.3	O2—C18—C19	115.5 (2)
C4—C5—H5	120.3	C17—C18—C19	118.4 (2)
C5—C6—C7	122.2 (2)	N2—C19—C14	118.9 (2)
C5—C6—H6	118.9	N2—C19—C18	119.5 (2)
C7—C6—H6	118.9	C14—C19—C18	121.6 (2)
C8—C7—C6	120.2 (2)

N1—Sn1—O1—C8	−7.95 (15)	C3—C4—C9—N1	1.3 (3)
Cl1—Sn1—O1—C8	171.04 (14)	C5—C4—C9—N1	−178.8 (2)
Cl2—Sn1—O1—C8	−4.8 (4)	C3—C4—C9—C8	−179.0 (2)
Cl3—Sn1—O1—C8	−96.33 (14)	C5—C4—C9—C8	0.9 (3)
Cl4—Sn1—O1—C8	79.48 (14)	O1—C8—C9—N1	−2.5 (3)
O1—Sn1—N1—C1	−176.9 (2)	C7—C8—C9—N1	177.7 (2)
Cl2—Sn1—N1—C1	3.69 (19)	O1—C8—C9—C4	177.8 (2)
Cl3—Sn1—N1—C1	−87.52 (19)	C7—C8—C9—C4	−2.0 (3)
Cl4—Sn1—N1—C1	94.85 (19)	C19—N2—C11—C12	−0.6 (4)
O1—Sn1—N1—C9	6.51 (14)	C19—N2—C11—C10	177.8 (2)
Cl2—Sn1—N1—C9	−172.94 (14)	N2—C11—C12—C13	−0.6 (4)
Cl3—Sn1—N1—C9	95.84 (14)	C10—C11—C12—C13	−179.0 (2)
Cl4—Sn1—N1—C9	−81.79 (14)	C11—C12—C13—C14	0.6 (4)
C9—N1—C1—C2	0.8 (3)	C12—C13—C14—C19	0.6 (4)
Sn1—N1—C1—C2	−175.60 (17)	C12—C13—C14—C15	179.9 (2)
N1—C1—C2—C3	0.3 (4)	C19—C14—C15—C16	0.4 (4)
C1—C2—C3—C4	−0.6 (4)	C13—C14—C15—C16	−178.9 (2)
C2—C3—C4—C9	−0.1 (3)	C14—C15—C16—C17	1.1 (4)
C2—C3—C4—C5	179.9 (2)	C15—C16—C17—C18	−0.9 (4)
C3—C4—C5—C6	−179.4 (2)	C16—C17—C18—O2	177.8 (2)
C9—C4—C5—C6	0.7 (3)	C16—C17—C18—C19	−0.6 (4)
C4—C5—C6—C7	−1.2 (4)	C11—N2—C19—C14	1.9 (4)
C5—C6—C7—C8	0.1 (4)	C11—N2—C19—C18	−177.3 (2)
Sn1—O1—C8—C7	−171.77 (18)	C15—C14—C19—N2	178.8 (2)
Sn1—O1—C8—C9	8.4 (3)	C13—C14—C19—N2	−1.8 (3)
C6—C7—C8—O1	−178.3 (2)	C15—C14—C19—C18	−2.0 (4)
C6—C7—C8—C9	1.5 (3)	C13—C14—C19—C18	177.4 (2)
C1—N1—C9—C4	−1.6 (3)	O2—C18—C19—N2	2.7 (3)
Sn1—N1—C9—C4	175.39 (17)	C17—C18—C19—N2	−178.7 (2)
C1—N1—C9—C8	178.7 (2)	O2—C18—C19—C14	−176.5 (2)
Sn1—N1—C9—C8	−4.3 (2)	C17—C18—C19—C14	2.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.84 (1)	1.86 (1)	2.683 (2)	168 (3)
N2—H2···O2	0.88 (1)	2.33 (2)	2.667 (3)	103 (2)

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[Sn(C₉H₆NO)Cl₄]
M_r	564.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.9431 (3), 11.5892 (4), 20.1795 (8)
β (°)	101.347 (4)
V (Å³)	2050.59 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.616, 0.717
No. of measured, independent and observed [I > 2σ(I)] reflections	13674, 4723, 4222
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.055, 1.06
No. of reflections	4723
No. of parameters	262
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.54

Computer programs: CrysAlis PRO (Agilent, 2012), 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—H1···O1	0.84 (1)	1.86 (1)	2.683 (2)	168 (3)

Acknowledgements

We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m241. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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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