Triethyl-ammonium tetra-chlorido(pyridine-2-carboxyl-ato-κN,O)stannate(IV).

The cation and the anion in the title salt, (C(6)H(16)N)[SnCl(4)(C(6)H(4)NO(2))], are linked by an N-H⋯O hydrogen bond. The Sn(IV) atom in the stannate anion is chelated by the pyridine-2-carboxyl-ate group and exists in a cis-SnCl(4)NO octa-hedral 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 = 484.79

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.048

S = 1.01

4344 reflections

242 parameters

25 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005460/si2335sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C6H16N)[SnCl4(C6H4NO2)]	F(000) = 960
Mr = 484.79	Dx = 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

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

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(Fo2) + (0.0213P)2 + 0.5451P] where P = (Fo2 + 2Fc2)/3
4344 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.41 e Å−3
25 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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