Triethyl­ammonium tetra­chlorido(pyridine-2-carboxyl­ato-κ2N,O)stannate(IV)

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

doi:10.1107/S1600536811005460

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m351

doi:10.1107/S1600536811005460

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Triethylammonium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV)

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

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 February 2011; accepted 14 February 2011; online 19 February 2011)

The cation and the anion in the title salt, (C₆H₁₆N)[SnCl₄(C₆H₄NO₂)], are linked by an N—H⋯O hydrogen bond. The Sn^IV atom in the stannate anion is chelated by the pyridine-2-carboxylate group and exists in a cis-SnCl₄NO octahedral geometry. The cation is disordered over two positions in a 0.564 (1):0.436 (1) ratio.

Related literature

For another ammonium tetrachlorido(pyridine-2-carboxylato)stannate, see: Najafi et al. (2011 ).

Experimental

Crystal data

(C₆H₁₆N)[SnCl₄(C₆H₄NO₂)]
M_r = 484.79
Monoclinic, P 2₁ /n
a = 11.6310 (7) Å
b = 10.4912 (6) Å
c = 16.4452 (9) Å
β = 109.672 (1)°
V = 1889.57 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.92 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.596, T_max = 0.910
17476 measured reflections
4344 independent reflections
3896 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.01
4344 reflections
242 parameters
25 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.88	1.95	2.828 (4)	172
N2′—H2′⋯O2	0.88	2.02	2.895 (5)	173

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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/S1600536811005460/si2335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005460/si2335Isup2.hkl

checkCIF report

Comment top

In the reaction of pyridine-2-carboxylic acid and stannic chloride in methanol, one equivalent of the carboxylic acid is protonated at the amino site and is also esterified, the reaction yielding the salt, (C₇H₈NO₂)⁺ [SnCl₄(C₆H₄NO₂)]^-. The Sn^IV atom in the anion is N,O-chelated by the pyridine-2-carboxylate in a cis-SnNOCl₄ octahedral geometry (Najafi et al., 2011). In the present study, triethylamine was added to function as proton abstractor. The reaction affords a similar salt, (Et₃NH)⁺ [SnCl₄(C₆H₄NO₂)]^- (Scheme I, Fig. 1). The tin atom in the stannate is chelated by the pyridine-2-carboxylate group and it exists in a cis-SnCl₄NO octahedral geometry.

Related literature top

For another ammonium tetrachlorido(pyridine-2-carboxylato)stannate, see: Najafi et al. (2011).

Experimental top

The reaction was carried out under a nitrogen atmosphere. Pyridine-2-carboxylic acid (1.0 mmol, 0.12 g) and the triethylamine (1.0 mmol, 0.10 g) were dissolved in dry methanol (20 ml). Stannic chloride ((1.0 mmol, 0.35 g) was added to the mixture and stirred for 12 h. Suitable crystals were obtained by slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Et₃NH)⁺ [SnCl₄(C₆H₄NO₂)]^- at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the cation is not shown.

Triethylammonium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV) top

Crystal data top

(C₆H₁₆N)[SnCl₄(C₆H₄NO₂)]	F(000) = 960
M_r = 484.79	D_x = 1.704 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8286 reflections
a = 11.6310 (7) Å	θ = 2.3–28.3°
b = 10.4912 (6) Å	µ = 1.92 mm⁻¹
c = 16.4452 (9) Å	T = 100 K
β = 109.672 (1)°	Prism, colorless
V = 1889.57 (19) Å³	0.30 × 0.25 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4344 independent reflections
Radiation source: fine-focus sealed tube	3896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.596, T_max = 0.910	k = −13→13
17476 measured reflections	l = −19→21

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0213P)² + 0.5451P] where P = (F_o² + 2F_c²)/3
4344 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.41 e Å⁻³
25 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

(C₆H₁₆N)[SnCl₄(C₆H₄NO₂)]	V = 1889.57 (19) Å³
M_r = 484.79	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.6310 (7) Å	µ = 1.92 mm⁻¹
b = 10.4912 (6) Å	T = 100 K
c = 16.4452 (9) Å	0.30 × 0.25 × 0.05 mm
β = 109.672 (1)°

Data collection top

Bruker SMART APEX diffractometer	4344 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3896 reflections with I > 2σ(I)
T_min = 0.596, T_max = 0.910	R_int = 0.033
17476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	25 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
4344 reflections	Δρ_min = −0.39 e Å⁻³
242 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.563342 (11)	0.304590 (11)	0.743404 (8)	0.01440 (5)
Cl1	0.37811 (4)	0.38342 (5)	0.64455 (3)	0.02443 (11)
Cl2	0.47250 (5)	0.23860 (5)	0.84821 (3)	0.02561 (11)
Cl3	0.56293 (4)	0.08950 (4)	0.69586 (3)	0.01948 (10)
Cl4	0.67771 (4)	0.36886 (4)	0.65317 (3)	0.01872 (10)
O1	0.59288 (12)	0.48336 (12)	0.80497 (8)	0.0200 (3)
O2	0.69627 (13)	0.58704 (13)	0.92554 (9)	0.0263 (3)
N1	0.74369 (14)	0.28596 (14)	0.84631 (10)	0.0150 (3)
C1	0.68201 (17)	0.49487 (17)	0.87734 (12)	0.0187 (4)
C2	0.77238 (17)	0.38638 (17)	0.90022 (11)	0.0151 (4)
C3	0.87950 (17)	0.39107 (17)	0.96906 (12)	0.0183 (4)
H3	0.8968	0.4612	1.0079	0.022*
C4	0.96192 (18)	0.29127 (18)	0.98084 (12)	0.0207 (4)
H4	1.0377	0.2933	1.0269	0.025*
C5	0.93224 (19)	0.18882 (18)	0.92456 (12)	0.0208 (4)
H5	0.9873	0.1195	0.9317	0.025*
C6	0.82192 (18)	0.18857 (17)	0.85810 (12)	0.0189 (4)
H6	0.8009	0.1178	0.8199	0.023*
N2	0.5100 (3)	0.7717 (3)	0.8635 (2)	0.0168 (8)	0.564 (3)
H2	0.5718	0.7181	0.8804	0.020*	0.564 (3)
C7	0.5607 (4)	0.9017 (4)	0.8956 (3)	0.0209 (9)	0.564 (3)
H7A	0.6002	0.9376	0.8559	0.025*	0.564 (3)
H7B	0.4927	0.9589	0.8948	0.025*	0.564 (3)
C8	0.6523 (4)	0.8976 (4)	0.9858 (3)	0.0289 (9)	0.564 (3)
H8A	0.6834	0.9837	1.0035	0.043*	0.564 (3)
H8B	0.7203	0.8416	0.9868	0.043*	0.564 (3)
H8C	0.6130	0.8648	1.0256	0.043*	0.564 (3)
C9	0.4203 (3)	0.7295 (3)	0.9059 (2)	0.0227 (8)	0.564 (3)
H9A	0.3543	0.7936	0.8941	0.027*	0.564 (3)
H9B	0.4623	0.7263	0.9691	0.027*	0.564 (3)
C10	0.3642 (5)	0.6008 (5)	0.8754 (4)	0.0307 (12)	0.564 (3)
H10A	0.3067	0.5791	0.9053	0.046*	0.564 (3)
H10B	0.4286	0.5361	0.8882	0.046*	0.564 (3)
H10C	0.3207	0.6036	0.8130	0.046*	0.564 (3)
C11	0.4630 (14)	0.7685 (17)	0.7665 (4)	0.0215 (11)	0.564 (3)
H11A	0.4388	0.6801	0.7472	0.026*	0.564 (3)
H11B	0.5297	0.7934	0.7450	0.026*	0.564 (3)
C12	0.3551 (13)	0.8558 (13)	0.7272 (9)	0.0279 (18)	0.564 (3)
H12A	0.3340	0.8565	0.6643	0.042*	0.564 (3)
H12B	0.3762	0.9423	0.7497	0.042*	0.564 (3)
H12C	0.2852	0.8250	0.7422	0.042*	0.564 (3)
N2'	0.4707 (4)	0.7281 (4)	0.8540 (3)	0.0178 (10)	0.436 (3)
H2'	0.5376	0.6845	0.8801	0.021*	0.436 (3)
C7'	0.4711 (4)	0.8380 (4)	0.9124 (3)	0.0232 (11)	0.436 (3)
H7'A	0.4561	0.8058	0.9645	0.028*	0.436 (3)
H7'B	0.4036	0.8968	0.8822	0.028*	0.436 (3)
C8'	0.5902 (5)	0.9107 (6)	0.9395 (5)	0.0281 (14)	0.436 (3)
H8'A	0.5857	0.9819	0.9770	0.042*	0.436 (3)
H8'B	0.6050	0.9438	0.8882	0.042*	0.436 (3)
H8'C	0.6570	0.8537	0.9711	0.042*	0.436 (3)
C9'	0.3664 (5)	0.6386 (5)	0.8450 (4)	0.0206 (12)	0.436 (3)
H9'A	0.3600	0.5777	0.7977	0.025*	0.436 (3)
H9'B	0.2895	0.6881	0.8289	0.025*	0.436 (3)
C10'	0.3807 (5)	0.5650 (5)	0.9267 (4)	0.0288 (12)	0.436 (3)
H10D	0.3119	0.5061	0.9166	0.043*	0.436 (3)
H10E	0.3822	0.6245	0.9730	0.043*	0.436 (3)
H10F	0.4572	0.5167	0.9435	0.043*	0.436 (3)
C11'	0.4774 (19)	0.765 (2)	0.7673 (6)	0.0215 (11)	0.44
H11C	0.4877	0.6871	0.7366	0.026*	0.436 (3)
H11D	0.5502	0.8194	0.7762	0.026*	0.436 (3)
C12'	0.3646 (18)	0.8367 (19)	0.7110 (11)	0.0279 (18)	0.44
H12D	0.3698	0.8490	0.6533	0.042*	0.436 (3)
H12E	0.3603	0.9198	0.7370	0.042*	0.436 (3)
H12F	0.2913	0.7872	0.7066	0.042*	0.436 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01336 (7)	0.01342 (7)	0.01478 (7)	0.00074 (5)	0.00259 (5)	−0.00027 (5)
Cl1	0.0152 (2)	0.0307 (3)	0.0233 (2)	0.00400 (19)	0.00109 (19)	0.00435 (19)
Cl2	0.0271 (3)	0.0307 (3)	0.0228 (2)	0.0027 (2)	0.0133 (2)	0.0037 (2)
Cl3	0.0254 (2)	0.0132 (2)	0.0181 (2)	−0.00356 (17)	0.00515 (18)	−0.00112 (17)
Cl4	0.0195 (2)	0.0163 (2)	0.0205 (2)	−0.00436 (17)	0.00697 (18)	−0.00023 (17)
O1	0.0195 (7)	0.0164 (6)	0.0194 (7)	0.0054 (5)	0.0005 (6)	−0.0035 (5)
O2	0.0283 (8)	0.0197 (7)	0.0251 (7)	0.0066 (6)	0.0015 (6)	−0.0080 (6)
N1	0.0164 (8)	0.0141 (7)	0.0131 (7)	0.0015 (6)	0.0033 (6)	−0.0008 (6)
C1	0.0198 (10)	0.0157 (9)	0.0197 (9)	0.0019 (7)	0.0054 (8)	−0.0004 (7)
C2	0.0180 (9)	0.0149 (8)	0.0139 (9)	0.0008 (7)	0.0072 (7)	0.0005 (7)
C3	0.0204 (10)	0.0179 (9)	0.0146 (9)	0.0006 (7)	0.0033 (7)	−0.0012 (7)
C4	0.0187 (10)	0.0236 (10)	0.0159 (9)	0.0029 (8)	0.0008 (8)	0.0029 (7)
C5	0.0234 (10)	0.0183 (9)	0.0191 (10)	0.0073 (8)	0.0049 (8)	0.0024 (7)
C6	0.0221 (10)	0.0152 (9)	0.0192 (9)	0.0031 (7)	0.0069 (8)	−0.0005 (7)
N2	0.0134 (19)	0.018 (2)	0.0199 (17)	0.0040 (13)	0.0071 (15)	0.0005 (15)
C7	0.021 (2)	0.0159 (18)	0.028 (2)	0.0027 (15)	0.012 (2)	−0.0004 (19)
C8	0.036 (3)	0.028 (2)	0.026 (2)	−0.0108 (19)	0.015 (2)	−0.0077 (18)
C9	0.0178 (17)	0.0273 (19)	0.0266 (19)	−0.0008 (14)	0.0120 (15)	−0.0011 (15)
C10	0.030 (2)	0.027 (3)	0.038 (4)	−0.012 (2)	0.015 (3)	−0.003 (2)
C11	0.021 (3)	0.0250 (13)	0.0191 (10)	0.0037 (17)	0.0075 (11)	0.0019 (8)
C12	0.026 (2)	0.029 (4)	0.026 (5)	0.004 (2)	0.006 (2)	0.005 (3)
N2'	0.015 (3)	0.018 (3)	0.022 (2)	0.0004 (17)	0.009 (2)	0.0004 (19)
C7'	0.021 (2)	0.019 (2)	0.030 (3)	−0.0010 (18)	0.010 (2)	−0.0072 (19)
C8'	0.030 (4)	0.023 (3)	0.032 (4)	−0.005 (3)	0.012 (3)	−0.009 (3)
C9'	0.020 (3)	0.018 (3)	0.027 (3)	−0.002 (2)	0.013 (2)	−0.001 (2)
C10'	0.036 (3)	0.027 (3)	0.027 (3)	−0.005 (2)	0.016 (3)	0.001 (2)
C11'	0.021 (3)	0.0250 (13)	0.0191 (10)	0.0037 (17)	0.0075 (11)	0.0019 (8)
C12'	0.026 (2)	0.029 (4)	0.026 (5)	0.004 (2)	0.006 (2)	0.005 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.1039 (13)	C10—H10A	0.9800
Sn1—N1	2.2163 (15)	C10—H10B	0.9800
Sn1—Cl1	2.3686 (5)	C10—H10C	0.9800
Sn1—Cl3	2.3876 (5)	C11—C12	1.512 (8)
Sn1—Cl4	2.3990 (5)	C11—H11A	0.9900
Sn1—Cl2	2.4066 (5)	C11—H11B	0.9900
O1—C1	1.294 (2)	C12—H12A	0.9800
O2—C1	1.226 (2)	C12—H12B	0.9800
N1—C6	1.338 (2)	C12—H12C	0.9800
N1—C2	1.345 (2)	N2'—C7'	1.499 (5)
C1—C2	1.509 (2)	N2'—C9'	1.501 (5)
C2—C3	1.374 (3)	N2'—C11'	1.504 (7)
C3—C4	1.388 (3)	N2'—H2'	0.8800
C3—H3	0.9500	C7'—C8'	1.511 (6)
C4—C5	1.384 (3)	C7'—H7'A	0.9900
C4—H4	0.9500	C7'—H7'B	0.9900
C5—C6	1.377 (3)	C8'—H8'A	0.9800
C5—H5	0.9500	C8'—H8'B	0.9800
C6—H6	0.9500	C8'—H8'C	0.9800
N2—C11	1.503 (6)	C9'—C10'	1.509 (6)
N2—C9	1.503 (4)	C9'—H9'A	0.9900
N2—C7	1.508 (5)	C9'—H9'B	0.9900
N2—H2	0.8800	C10'—H10D	0.9800
C7—C8	1.508 (5)	C10'—H10E	0.9800
C7—H7A	0.9900	C10'—H10F	0.9800
C7—H7B	0.9900	C11'—C12'	1.524 (13)
C8—H8A	0.9800	C11'—H11C	0.9900
C8—H8B	0.9800	C11'—H11D	0.9900
C8—H8C	0.9800	C12'—H12D	0.9800
C9—C10	1.510 (5)	C12'—H12E	0.9800
C9—H9A	0.9900	C12'—H12F	0.9800
C9—H9B	0.9900

O1—Sn1—N1	75.63 (5)	C9—C10—H10A	109.5
O1—Sn1—Cl1	89.00 (4)	C9—C10—H10B	109.5
N1—Sn1—Cl1	164.42 (4)	H10A—C10—H10B	109.5
O1—Sn1—Cl3	169.14 (4)	C9—C10—H10C	109.5
N1—Sn1—Cl3	93.66 (4)	H10A—C10—H10C	109.5
Cl1—Sn1—Cl3	101.778 (17)	H10B—C10—H10C	109.5
O1—Sn1—Cl4	90.71 (4)	N2—C11—C12	113.1 (11)
N1—Sn1—Cl4	85.28 (4)	N2—C11—H11A	108.9
Cl1—Sn1—Cl4	92.462 (18)	C12—C11—H11A	108.9
Cl3—Sn1—Cl4	90.200 (16)	N2—C11—H11B	108.9
O1—Sn1—Cl2	87.23 (4)	C12—C11—H11B	108.9
N1—Sn1—Cl2	87.63 (4)	H11A—C11—H11B	107.8
Cl1—Sn1—Cl2	94.290 (18)	C11—C12—H12A	109.5
Cl3—Sn1—Cl2	90.554 (18)	C11—C12—H12B	109.5
Cl4—Sn1—Cl2	172.905 (17)	H12A—C12—H12B	109.5
C1—O1—Sn1	118.44 (11)	C11—C12—H12C	109.5
C6—N1—C2	119.80 (16)	H12A—C12—H12C	109.5
C6—N1—Sn1	126.91 (12)	H12B—C12—H12C	109.5
C2—N1—Sn1	113.29 (12)	C7'—N2'—C9'	111.9 (4)
O2—C1—O1	124.09 (17)	C7'—N2'—C11'	114.7 (10)
O2—C1—C2	120.18 (17)	C9'—N2'—C11'	111.5 (10)
O1—C1—C2	115.73 (16)	C7'—N2'—H2'	106.0
N1—C2—C3	121.77 (16)	C9'—N2'—H2'	106.0
N1—C2—C1	115.42 (16)	C11'—N2'—H2'	106.0
C3—C2—C1	122.75 (16)	N2'—C7'—C8'	112.5 (4)
C2—C3—C4	118.69 (17)	N2'—C7'—H7'A	109.1
C2—C3—H3	120.7	C8'—C7'—H7'A	109.1
C4—C3—H3	120.7	N2'—C7'—H7'B	109.1
C5—C4—C3	119.16 (18)	C8'—C7'—H7'B	109.1
C5—C4—H4	120.4	H7'A—C7'—H7'B	107.8
C3—C4—H4	120.4	C7'—C8'—H8'A	109.5
C6—C5—C4	119.22 (17)	C7'—C8'—H8'B	109.5
C6—C5—H5	120.4	H8'A—C8'—H8'B	109.5
C4—C5—H5	120.4	C7'—C8'—H8'C	109.5
N1—C6—C5	121.32 (17)	H8'A—C8'—H8'C	109.5
N1—C6—H6	119.3	H8'B—C8'—H8'C	109.5
C5—C6—H6	119.3	N2'—C9'—C10'	112.9 (5)
C11—N2—C9	115.1 (7)	N2'—C9'—H9'A	109.0
C11—N2—C7	110.6 (8)	C10'—C9'—H9'A	109.0
C9—N2—C7	110.8 (3)	N2'—C9'—H9'B	109.0
C11—N2—H2	106.6	C10'—C9'—H9'B	109.0
C9—N2—H2	106.6	H9'A—C9'—H9'B	107.8
C7—N2—H2	106.6	C9'—C10'—H10D	109.5
C8—C7—N2	112.4 (4)	C9'—C10'—H10E	109.5
C8—C7—H7A	109.1	H10D—C10'—H10E	109.5
N2—C7—H7A	109.1	C9'—C10'—H10F	109.5
C8—C7—H7B	109.1	H10D—C10'—H10F	109.5
N2—C7—H7B	109.1	H10E—C10'—H10F	109.5
H7A—C7—H7B	107.8	N2'—C11'—C12'	113.2 (14)
C7—C8—H8A	109.5	N2'—C11'—H11C	108.9
C7—C8—H8B	109.5	C12'—C11'—H11C	108.9
H8A—C8—H8B	109.5	N2'—C11'—H11D	108.9
C7—C8—H8C	109.5	C12'—C11'—H11D	108.9
H8A—C8—H8C	109.5	H11C—C11'—H11D	107.7
H8B—C8—H8C	109.5	C11'—C12'—H12D	109.5
N2—C9—C10	113.6 (3)	C11'—C12'—H12E	109.5
N2—C9—H9A	108.8	H12D—C12'—H12E	109.5
C10—C9—H9A	108.8	C11'—C12'—H12F	109.5
N2—C9—H9B	108.8	H12D—C12'—H12F	109.5
C10—C9—H9B	108.8	H12E—C12'—H12F	109.5
H9A—C9—H9B	107.7

N1—Sn1—O1—C1	−11.42 (13)	O1—C1—C2—N1	−5.5 (2)
Cl1—Sn1—O1—C1	171.18 (14)	O2—C1—C2—C3	−7.3 (3)
Cl3—Sn1—O1—C1	−1.6 (3)	O1—C1—C2—C3	171.81 (17)
Cl4—Sn1—O1—C1	−96.37 (14)	N1—C2—C3—C4	2.5 (3)
Cl2—Sn1—O1—C1	76.84 (14)	C1—C2—C3—C4	−174.58 (18)
O1—Sn1—N1—C6	−171.97 (17)	C2—C3—C4—C5	−1.8 (3)
Cl1—Sn1—N1—C6	−162.25 (12)	C3—C4—C5—C6	0.2 (3)
Cl3—Sn1—N1—C6	9.87 (16)	C2—N1—C6—C5	−0.2 (3)
Cl4—Sn1—N1—C6	−80.03 (15)	Sn1—N1—C6—C5	179.52 (14)
Cl2—Sn1—N1—C6	100.27 (16)	C4—C5—C6—N1	0.8 (3)
O1—Sn1—N1—C2	7.73 (12)	C11—N2—C7—C8	−156.5 (7)
Cl1—Sn1—N1—C2	17.5 (2)	C9—N2—C7—C8	74.7 (4)
Cl3—Sn1—N1—C2	−170.42 (12)	C11—N2—C9—C10	52.6 (8)
Cl4—Sn1—N1—C2	99.68 (12)	C7—N2—C9—C10	179.0 (4)
Cl2—Sn1—N1—C2	−80.02 (12)	C9—N2—C11—C12	61.6 (14)
Sn1—O1—C1—O2	−167.96 (16)	C7—N2—C11—C12	−64.9 (13)
Sn1—O1—C1—C2	12.9 (2)	C9'—N2'—C7'—C8'	166.0 (5)
C6—N1—C2—C3	−1.5 (3)	C11'—N2'—C7'—C8'	−65.8 (10)
Sn1—N1—C2—C3	178.74 (14)	C7'—N2'—C9'—C10'	−69.7 (6)
C6—N1—C2—C1	175.77 (17)	C11'—N2'—C9'—C10'	160.4 (10)
Sn1—N1—C2—C1	−4.0 (2)	C7'—N2'—C11'—C12'	−66.1 (18)
O2—C1—C2—N1	175.38 (18)	C9'—N2'—C11'—C12'	62.3 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88	1.95	2.828 (4)	172
N2′—H2′···O2	0.88	2.02	2.895 (5)	173

Experimental details

Crystal data
Chemical formula	(C₆H₁₆N)[SnCl₄(C₆H₄NO₂)]
M_r	484.79
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.6310 (7), 10.4912 (6), 16.4452 (9)
β (°)	109.672 (1)
V (Å³)	1889.57 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.92
Crystal size (mm)	0.30 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.596, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	17476, 4344, 3896
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.01
No. of reflections	4344
No. of parameters	242
No. of restraints	25
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.39

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N2—H2···O2	0.88	1.95	2.828 (4)	172
N2'—H2'···O2	0.88	2.02	2.895 (5)	173

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m239. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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