10-Hy­droxy­benzo[h]quinolin-1-ium tetra­chlorido(pyridine-2-carboxyl­ato-κ2N,O)stannate(IV) methanol monosolvate

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

doi:10.1107/S1600536812019605

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m743

doi:10.1107/S1600536812019605

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10-Hydroxybenzo[h]quinolin-1-ium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV) methanol monosolvate

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 1 May 2012; accepted 2 May 2012; online 5 May 2012)

The reaction of 4-(dimethylamino)pyridine, picolinic acid and stannic chloride yields the title monosolvated salt, (C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)]·CH₃OH. The Sn^IV atom is N,O-chelated by the picolinate ion in a cis-SnNOCl₄ octahedral geometry. The cation is linked to the methanol solvent molecule by an O—H⋯O hydrogen bond; the solvent molecule itself is a hydrogen-bond donor to the uncoordinating carboxylate O atom of the anion. The cations and anions are linked by weak N—H⋯Cl interactions, forming a chain running along the b axis.

Related literature

For a tetrachlorido(pyridine-2-carboxylato)stannate(IV), see: Najafi et al. (2012 ).

Experimental

Crystal data

(C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)]·CH₄O
M_r = 610.85
Monoclinic, C 2/c
a = 31.5065 (11) Å
b = 8.0802 (2) Å
c = 20.0948 (9) Å
β = 115.722 (5)°
V = 4608.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.60 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.645, T_max = 0.856
15316 measured reflections
5326 independent reflections
4445 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.065
S = 1.02
5326 reflections
293 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.84 (1)	1.73 (1)	2.554 (2)	170 (3)
O4—H4⋯O2	0.83 (1)	1.87 (1)	2.698 (3)	174 (3)
N2—H2⋯Cl4ⁱ	0.87 (1)	2.58 (2)	3.255 (2)	135 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536812019605/hg5222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019605/hg5222Isup2.hkl

checkCIF report

Comment top

A previous study reported 4-(dimethylamino)pyridinium tetrachlorido(pyridine-2-carboxylato)stannate, which was synthesized by the reaction of 4-(dimethylamino)pyridine, picolinic acid and stannic chloride in methanol (Najafi et al., 2012). The reaction with 10-hydroxybenzo[h]quinoline in place of 4-(dimethylamino)pyridine yielded the analogous salt, (C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)] as a methanol monosolvate (Scheme I). The Sn^IV atom is N,O-chelated by the picolinate ion in a cis-SnNOCl₄ octahedral geometry. The cation is linked to the methanol molecule by an O–H···O hydrogen bond; the solvent molecule itself is hydrogen-bond donor to the double-bond carboxyl O atom of the anion (Table 1).

Related literature top

For a tetrachlorido(pyridine-2-carboxylato)stannate, see: Najafi et al. (2012).

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol), picolinic acid (0.12 g, 1 mmol) and 10-hydroxybenzo[h]quinoline (0.20 g, 1 mmol) were loaded into a convection tube; the tube was filled with dry methanol 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 (C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)]^.CH₃OH at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

10-Hydroxybenzo[h]quinolin-1-ium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV) methanol monosolvate top

Crystal data top

(C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)]·CH₄O	F(000) = 2416
M_r = 610.85	D_x = 1.761 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6804 reflections
a = 31.5065 (11) Å	θ = 2.6–27.5°
b = 8.0802 (2) Å	µ = 1.60 mm⁻¹
c = 20.0948 (9) Å	T = 100 K
β = 115.722 (5)°	Prism, yellow
V = 4608.8 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5326 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4445 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ω scan	h = −29→40
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
T_min = 0.645, T_max = 0.856	l = −26→16
15316 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0262P)² + 2.9883P] where P = (F_o² + 2F_c²)/3
5326 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.51 e Å⁻³
3 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

(C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)]·CH₄O	V = 4608.8 (3) Å³
M_r = 610.85	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 31.5065 (11) Å	µ = 1.60 mm⁻¹
b = 8.0802 (2) Å	T = 100 K
c = 20.0948 (9) Å	0.30 × 0.20 × 0.10 mm
β = 115.722 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5326 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	4445 reflections with I > 2σ(I)
T_min = 0.645, T_max = 0.856	R_int = 0.033
15316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	3 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.51 e Å⁻³
5326 reflections	Δρ_min = −0.44 e Å⁻³
293 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.341644 (5)	0.660077 (19)	0.666671 (10)	0.01289 (6)
Cl1	0.37922 (2)	0.39689 (7)	0.68079 (4)	0.02026 (14)
Cl2	0.40850 (2)	0.82509 (7)	0.68449 (4)	0.02084 (15)
Cl3	0.31336 (2)	0.66098 (8)	0.53578 (4)	0.02510 (15)
Cl4	0.36197 (2)	0.66555 (8)	0.79760 (4)	0.02179 (15)
O1	0.27693 (5)	0.5575 (2)	0.65110 (10)	0.0169 (4)
O2	0.20485 (6)	0.6113 (2)	0.64027 (11)	0.0225 (4)
O3	0.07905 (6)	0.2706 (2)	0.53486 (11)	0.0217 (4)
O4	0.16051 (6)	0.3577 (2)	0.54923 (12)	0.0238 (4)
N1	0.29836 (7)	0.8782 (2)	0.66282 (12)	0.0144 (4)
N2	0.02661 (7)	0.1368 (3)	0.58997 (13)	0.0172 (5)
C1	0.24389 (8)	0.6557 (3)	0.64886 (14)	0.0153 (5)
C2	0.25594 (8)	0.8378 (3)	0.65863 (14)	0.0148 (5)
C3	0.22558 (9)	0.9549 (3)	0.66296 (15)	0.0191 (6)
H3A	0.1957	0.9238	0.6599	0.023*
C4	0.23938 (9)	1.1189 (3)	0.67188 (16)	0.0215 (6)
H4A	0.2192	1.2022	0.6753	0.026*
C5	0.28285 (10)	1.1601 (3)	0.67575 (18)	0.0253 (7)
H5	0.2928	1.2723	0.6813	0.030*
C6	0.31165 (9)	1.0370 (3)	0.67148 (16)	0.0209 (6)
H6	0.3418	1.0654	0.6748	0.025*
C7	0.02266 (9)	0.0482 (3)	0.64277 (15)	0.0200 (6)
H7	0.0501	0.0137	0.6846	0.024*
C8	−0.02144 (9)	0.0061 (3)	0.63690 (16)	0.0207 (6)
H8	−0.0246	−0.0580	0.6741	0.025*
C9	−0.06052 (9)	0.0593 (3)	0.57607 (16)	0.0192 (6)
H9	−0.0910	0.0315	0.5714	0.023*
C10	−0.05622 (9)	0.1538 (3)	0.52073 (15)	0.0173 (5)
C11	−0.09634 (9)	0.2137 (3)	0.45798 (16)	0.0214 (6)
H11	−0.1271	0.1894	0.4528	0.026*
C12	−0.09079 (9)	0.3046 (3)	0.40608 (16)	0.0228 (6)
H12	−0.1180	0.3440	0.3650	0.027*
C13	−0.04506 (9)	0.3436 (3)	0.41098 (15)	0.0191 (6)
C14	−0.04056 (9)	0.4373 (3)	0.35614 (16)	0.0236 (6)
H14	−0.0680	0.4748	0.3149	0.028*
C15	0.00334 (9)	0.4759 (3)	0.36123 (16)	0.0240 (6)
H15	0.0059	0.5400	0.3235	0.029*
C16	0.04405 (9)	0.4220 (3)	0.42113 (16)	0.0208 (6)
H16	0.0741	0.4495	0.4240	0.025*
C17	0.04076 (9)	0.3285 (3)	0.47630 (15)	0.0172 (5)
C18	−0.00405 (9)	0.2878 (3)	0.47287 (15)	0.0166 (5)
C19	−0.01061 (8)	0.1925 (3)	0.52815 (15)	0.0153 (5)
C20	0.18022 (11)	0.3508 (4)	0.49717 (18)	0.0330 (7)
H20A	0.1712	0.4503	0.4662	0.050*
H20B	0.1683	0.2525	0.4659	0.050*
H20C	0.2146	0.3448	0.5237	0.050*
H2	0.0542 (6)	0.171 (3)	0.5956 (17)	0.027 (8)*
H3	0.1041 (7)	0.306 (4)	0.5351 (19)	0.042 (10)*
H4	0.1730 (9)	0.434 (2)	0.5790 (13)	0.021 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01130 (9)	0.01287 (9)	0.01497 (11)	−0.00094 (7)	0.00613 (7)	−0.00093 (7)
Cl1	0.0175 (3)	0.0155 (3)	0.0278 (4)	0.0006 (3)	0.0098 (3)	−0.0006 (3)
Cl2	0.0182 (3)	0.0206 (3)	0.0289 (4)	−0.0060 (3)	0.0151 (3)	−0.0059 (3)
Cl3	0.0224 (3)	0.0360 (4)	0.0157 (4)	0.0055 (3)	0.0071 (3)	−0.0004 (3)
Cl4	0.0147 (3)	0.0370 (4)	0.0143 (3)	0.0024 (3)	0.0068 (3)	0.0010 (3)
O1	0.0114 (8)	0.0143 (8)	0.0242 (11)	−0.0025 (7)	0.0072 (8)	−0.0018 (7)
O2	0.0135 (9)	0.0271 (10)	0.0276 (12)	−0.0053 (8)	0.0096 (9)	−0.0072 (9)
O3	0.0120 (9)	0.0288 (10)	0.0226 (12)	−0.0037 (8)	0.0058 (8)	0.0051 (8)
O4	0.0198 (10)	0.0308 (11)	0.0220 (12)	−0.0108 (9)	0.0101 (9)	−0.0093 (9)
N1	0.0184 (10)	0.0129 (10)	0.0136 (12)	0.0004 (9)	0.0084 (9)	0.0013 (9)
N2	0.0138 (10)	0.0201 (11)	0.0179 (13)	−0.0030 (9)	0.0070 (10)	−0.0010 (9)
C1	0.0141 (12)	0.0193 (12)	0.0118 (14)	−0.0012 (10)	0.0050 (11)	−0.0017 (10)
C2	0.0147 (12)	0.0179 (12)	0.0106 (13)	−0.0003 (10)	0.0045 (11)	−0.0011 (10)
C3	0.0147 (12)	0.0247 (14)	0.0179 (15)	0.0033 (11)	0.0069 (11)	0.0009 (11)
C4	0.0242 (14)	0.0214 (13)	0.0218 (17)	0.0083 (12)	0.0128 (13)	0.0048 (12)
C5	0.0342 (16)	0.0137 (13)	0.0355 (19)	0.0010 (12)	0.0221 (15)	0.0026 (12)
C6	0.0221 (13)	0.0178 (12)	0.0293 (18)	−0.0016 (11)	0.0173 (13)	0.0020 (11)
C7	0.0200 (13)	0.0223 (13)	0.0164 (15)	−0.0016 (11)	0.0067 (12)	−0.0002 (11)
C8	0.0215 (13)	0.0229 (13)	0.0198 (16)	−0.0015 (12)	0.0110 (12)	0.0002 (12)
C9	0.0161 (12)	0.0232 (13)	0.0221 (16)	−0.0039 (11)	0.0118 (12)	−0.0057 (11)
C10	0.0161 (12)	0.0194 (13)	0.0168 (15)	−0.0009 (11)	0.0074 (11)	−0.0043 (11)
C11	0.0118 (12)	0.0288 (14)	0.0238 (17)	−0.0021 (11)	0.0079 (12)	−0.0063 (12)
C12	0.0153 (13)	0.0290 (14)	0.0182 (16)	0.0006 (11)	0.0017 (12)	0.0000 (12)
C13	0.0180 (13)	0.0210 (13)	0.0167 (15)	−0.0010 (11)	0.0062 (12)	−0.0013 (11)
C14	0.0186 (13)	0.0282 (15)	0.0191 (16)	0.0016 (12)	0.0036 (12)	0.0033 (12)
C15	0.0261 (14)	0.0266 (14)	0.0183 (16)	−0.0019 (12)	0.0087 (13)	0.0041 (12)
C16	0.0175 (13)	0.0250 (14)	0.0217 (17)	−0.0048 (11)	0.0101 (12)	−0.0027 (12)
C17	0.0152 (12)	0.0174 (12)	0.0163 (15)	−0.0022 (10)	0.0044 (11)	−0.0035 (11)
C18	0.0155 (12)	0.0159 (12)	0.0169 (15)	−0.0036 (10)	0.0056 (11)	−0.0038 (11)
C19	0.0134 (12)	0.0160 (12)	0.0150 (14)	−0.0023 (10)	0.0047 (11)	−0.0046 (10)
C20	0.0347 (17)	0.0435 (18)	0.0256 (19)	−0.0095 (14)	0.0175 (15)	−0.0087 (14)

Geometric parameters (Å, º) top

Sn1—O1	2.0949 (15)	C7—C8	1.385 (3)
Sn1—N1	2.2092 (19)	C7—H7	0.9500
Sn1—Cl3	2.3828 (7)	C8—C9	1.374 (4)
Sn1—Cl2	2.3851 (6)	C8—H8	0.9500
Sn1—Cl1	2.3903 (6)	C9—C10	1.403 (4)
Sn1—Cl4	2.4231 (7)	C9—H9	0.9500
O1—C1	1.294 (3)	C10—C19	1.414 (3)
O2—C1	1.220 (3)	C10—C11	1.428 (4)
O3—C17	1.352 (3)	C11—C12	1.347 (4)
O3—H3	0.835 (10)	C11—H11	0.9500
O4—C20	1.431 (3)	C12—C13	1.436 (3)
O4—H4	0.831 (10)	C12—H12	0.9500
N1—C6	1.338 (3)	C13—C14	1.394 (4)
N1—C2	1.342 (3)	C13—C18	1.423 (4)
N2—C7	1.330 (3)	C14—C15	1.377 (3)
N2—C19	1.363 (3)	C14—H14	0.9500
N2—H2	0.870 (10)	C15—C16	1.394 (4)
C1—C2	1.511 (3)	C15—H15	0.9500
C2—C3	1.375 (3)	C16—C17	1.382 (4)
C3—C4	1.381 (4)	C16—H16	0.9500
C3—H3A	0.9500	C17—C18	1.422 (3)
C4—C5	1.378 (4)	C18—C19	1.438 (3)
C4—H4A	0.9500	C20—H20A	0.9800
C5—C6	1.373 (3)	C20—H20B	0.9800
C5—H5	0.9500	C20—H20C	0.9800
C6—H6	0.9500

O1—Sn1—N1	76.37 (7)	C8—C7—H7	119.9
O1—Sn1—Cl3	87.87 (5)	C9—C8—C7	118.5 (2)
N1—Sn1—Cl3	91.69 (6)	C9—C8—H8	120.7
O1—Sn1—Cl2	169.28 (5)	C7—C8—H8	120.7
N1—Sn1—Cl2	92.91 (5)	C8—C9—C10	121.2 (2)
Cl3—Sn1—Cl2	92.68 (2)	C8—C9—H9	119.4
O1—Sn1—Cl1	93.77 (5)	C10—C9—H9	119.4
N1—Sn1—Cl1	168.64 (5)	C9—C10—C19	118.7 (2)
Cl3—Sn1—Cl1	93.58 (2)	C9—C10—C11	122.1 (2)
Cl2—Sn1—Cl1	96.88 (2)	C19—C10—C11	119.2 (2)
O1—Sn1—Cl4	87.18 (5)	C12—C11—C10	120.4 (2)
N1—Sn1—Cl4	83.78 (6)	C12—C11—H11	119.8
Cl3—Sn1—Cl4	173.96 (2)	C10—C11—H11	119.8
Cl2—Sn1—Cl4	91.54 (2)	C11—C12—C13	122.0 (3)
Cl1—Sn1—Cl4	90.20 (2)	C11—C12—H12	119.0
C1—O1—Sn1	118.61 (15)	C13—C12—H12	119.0
C17—O3—H3	112 (2)	C14—C13—C18	119.9 (2)
C20—O4—H4	109.5 (19)	C14—C13—C12	120.6 (2)
C6—N1—C2	119.2 (2)	C18—C13—C12	119.6 (2)
C6—N1—Sn1	127.39 (16)	C15—C14—C13	120.5 (3)
C2—N1—Sn1	113.00 (15)	C15—C14—H14	119.8
C7—N2—C19	124.3 (2)	C13—C14—H14	119.8
C7—N2—H2	120 (2)	C14—C15—C16	120.8 (3)
C19—N2—H2	115 (2)	C14—C15—H15	119.6
O2—C1—O1	124.9 (2)	C16—C15—H15	119.6
O2—C1—C2	119.1 (2)	C17—C16—C15	120.1 (2)
O1—C1—C2	116.1 (2)	C17—C16—H16	119.9
N1—C2—C3	122.0 (2)	C15—C16—H16	119.9
N1—C2—C1	115.6 (2)	O3—C17—C16	122.6 (2)
C3—C2—C1	122.4 (2)	O3—C17—C18	117.0 (2)
C2—C3—C4	118.7 (2)	C16—C17—C18	120.4 (2)
C2—C3—H3A	120.7	C17—C18—C13	118.4 (2)
C4—C3—H3A	120.7	C17—C18—C19	124.0 (2)
C5—C4—C3	119.2 (2)	C13—C18—C19	117.7 (2)
C5—C4—H4A	120.4	N2—C19—C10	117.1 (2)
C3—C4—H4A	120.4	N2—C19—C18	121.7 (2)
C6—C5—C4	119.3 (2)	C10—C19—C18	121.1 (2)
C6—C5—H5	120.4	O4—C20—H20A	109.5
C4—C5—H5	120.4	O4—C20—H20B	109.5
N1—C6—C5	121.6 (2)	H20A—C20—H20B	109.5
N1—C6—H6	119.2	O4—C20—H20C	109.5
C5—C6—H6	119.2	H20A—C20—H20C	109.5
N2—C7—C8	120.1 (3)	H20B—C20—H20C	109.5
N2—C7—H7	119.9

N1—Sn1—O1—C1	−2.17 (18)	N2—C7—C8—C9	−0.6 (4)
Cl3—Sn1—O1—C1	−94.42 (18)	C7—C8—C9—C10	0.1 (4)
Cl2—Sn1—O1—C1	−1.2 (4)	C8—C9—C10—C19	0.7 (4)
Cl1—Sn1—O1—C1	172.13 (18)	C8—C9—C10—C11	−178.4 (2)
Cl4—Sn1—O1—C1	82.12 (18)	C9—C10—C11—C12	179.8 (2)
O1—Sn1—N1—C6	177.6 (2)	C19—C10—C11—C12	0.7 (4)
Cl3—Sn1—N1—C6	−95.0 (2)	C10—C11—C12—C13	0.5 (4)
Cl2—Sn1—N1—C6	−2.2 (2)	C11—C12—C13—C14	179.7 (3)
Cl1—Sn1—N1—C6	147.4 (2)	C11—C12—C13—C18	−1.1 (4)
Cl4—Sn1—N1—C6	89.0 (2)	C18—C13—C14—C15	0.2 (4)
O1—Sn1—N1—C2	4.76 (17)	C12—C13—C14—C15	179.4 (3)
Cl3—Sn1—N1—C2	92.16 (17)	C13—C14—C15—C16	0.1 (4)
Cl2—Sn1—N1—C2	−175.07 (17)	C14—C15—C16—C17	0.1 (4)
Cl1—Sn1—N1—C2	−25.5 (4)	C15—C16—C17—O3	178.8 (2)
Cl4—Sn1—N1—C2	−83.84 (17)	C15—C16—C17—C18	−0.6 (4)
Sn1—O1—C1—O2	−179.9 (2)	O3—C17—C18—C13	−178.5 (2)
Sn1—O1—C1—C2	−0.6 (3)	C16—C17—C18—C13	0.9 (4)
C6—N1—C2—C3	0.0 (4)	O3—C17—C18—C19	1.1 (4)
Sn1—N1—C2—C3	173.5 (2)	C16—C17—C18—C19	−179.4 (2)
C6—N1—C2—C1	180.0 (2)	C14—C13—C18—C17	−0.7 (4)
Sn1—N1—C2—C1	−6.5 (3)	C12—C13—C18—C17	−179.9 (2)
O2—C1—C2—N1	−175.7 (2)	C14—C13—C18—C19	179.6 (2)
O1—C1—C2—N1	4.9 (3)	C12—C13—C18—C19	0.4 (4)
O2—C1—C2—C3	4.3 (4)	C7—N2—C19—C10	0.5 (4)
O1—C1—C2—C3	−175.1 (3)	C7—N2—C19—C18	−179.9 (2)
N1—C2—C3—C4	0.0 (4)	C9—C10—C19—N2	−1.0 (3)
C1—C2—C3—C4	−180.0 (2)	C11—C10—C19—N2	178.1 (2)
C2—C3—C4—C5	0.4 (4)	C9—C10—C19—C18	179.5 (2)
C3—C4—C5—C6	−0.7 (4)	C11—C10—C19—C18	−1.4 (4)
C2—N1—C6—C5	−0.4 (4)	C17—C18—C19—N2	1.7 (4)
Sn1—N1—C6—C5	−172.9 (2)	C13—C18—C19—N2	−178.7 (2)
C4—C5—C6—N1	0.8 (5)	C17—C18—C19—C10	−178.8 (2)
C19—N2—C7—C8	0.3 (4)	C13—C18—C19—C10	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84 (1)	1.73 (1)	2.554 (2)	170 (3)
O4—H4···O2	0.83 (1)	1.87 (1)	2.698 (3)	174 (3)
N2—H2···Cl4ⁱ	0.87 (1)	2.58 (2)	3.255 (2)	135 (2)

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	(C₁₃H₁₀NO)[SnCl₄(C₆H₄NO₂)]·CH₄O
M_r	610.85
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	31.5065 (11), 8.0802 (2), 20.0948 (9)
β (°)	115.722 (5)
V (Å³)	4608.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.60
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.645, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	15316, 5326, 4445
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.065, 1.02
No. of reflections	5326
No. of parameters	293
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.44

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
O3—H3···O4	0.84 (1)	1.73 (1)	2.554 (2)	170 (3)
O4—H4···O2	0.83 (1)	1.87 (1)	2.698 (3)	174 (3)
N2—H2···Cl4ⁱ	0.87 (1)	2.58 (2)	3.255 (2)	135 (2)

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

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, 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. (2012). Acta Cryst. E68, m744. 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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