2-Meth-oxy-carbonyl-pyridinium tetra-chlorido(pyridine-2-carboxyl-ato-κN,O)stannate(IV).

In the reaction of pyridine-2-carb-oxy-lic acid and stannic chloride in methanol, one equivalent of the carb-oxy-lic acid is protonated at the amino site and is also esterified, yielding the title salt, (C(7)H(8)NO(2))[SnCl(4)(C(6)H(4)NO(2))]. The Sn(IV) atom in the anion is N,O-chelated by a pyridine-2-carboxyl-ate in a cis-SnNOCl(4) octa-hedral geometry. The cation is linked to the anion by an N-H⋯O hydrogen bond.

Related literature

For a related organotin structure, see: Nowell et al. (1983 ▶).

Experimental

Crystal data

(C7H8NO2)[SnCl4(C6H4NO2)]

M = 520.74

Orthorhombic,

a = 8.8898 (3) Å

b = 10.3571 (3) Å

c = 20.0938 (7) Å

V = 1850.09 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.98 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 Technologies, 2010 ▶) T min = 0.588, T max = 0.693

6191 measured reflections

3787 independent reflections

3679 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.049

S = 0.96

3787 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.68 e Å−3

Absolute structure: Flack (1983 ▶), 1428 Friedel pairs

Flack parameter: −0.03 (2)

Data collection: CrysAlis PRO (Agilent Technologies, 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001930/si2326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001930/si2326Isup2.hkl

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

(C7H8NO2)[SnCl4(C6H4NO2)]	F(000) = 1016
Mr = 520.74	Dx = 1.870 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5063 reflections
a = 8.8898 (3) Å	θ = 2.5–29.3°
b = 10.3571 (3) Å	µ = 1.98 mm−1
c = 20.0938 (7) Å	T = 100 K
V = 1850.09 (10) Å3	Prism, colorless
Z = 4	0.30 × 0.25 × 0.20 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	3787 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3679 reflections with I > 2σ(I)
Mirror	Rint = 0.021
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −11→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −13→10
Tmin = 0.588, Tmax = 0.693	l = −25→15
6191 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.049	w = 1/[σ2(Fo2) + (0.0199P)2 + 1.6372P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
3787 reflections	Δρmax = 0.36 e Å−3
222 parameters	Δρmin = −0.68 e Å−3
1 restraint	Absolute structure: Flack (1983), 1428 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (2)

	x	y	z	Uiso*/Ueq
Sn1	0.389388 (18)	0.500107 (17)	0.098352 (8)	0.01202 (5)
Cl4	0.19677 (7)	0.49203 (9)	0.18312 (3)	0.01817 (13)
Cl3	0.59780 (8)	0.48209 (7)	0.02047 (3)	0.01800 (14)
Cl2	0.39844 (9)	0.72817 (6)	0.09456 (4)	0.02160 (15)
Cl1	0.21001 (8)	0.46486 (7)	0.01310 (4)	0.02040 (16)
O1	0.54531 (19)	0.5006 (2)	0.17598 (8)	0.0163 (4)
O2	0.6707 (2)	0.3817 (2)	0.24920 (10)	0.0217 (5)
O3	0.9194 (2)	0.2695 (2)	0.17094 (10)	0.0202 (4)
O4	1.1105 (3)	0.1264 (2)	0.16977 (11)	0.0271 (5)
N1	0.4309 (3)	0.2927 (2)	0.11697 (11)	0.0127 (5)
N2	0.9440 (3)	0.3078 (2)	0.30014 (13)	0.0148 (5)
H2	0.866 (2)	0.338 (3)	0.2787 (14)	0.012 (8)*
C1	0.5869 (3)	0.3918 (3)	0.20127 (13)	0.0156 (6)
C2	0.5262 (3)	0.2717 (3)	0.16754 (13)	0.0148 (6)
C3	0.5707 (4)	0.1491 (3)	0.18569 (14)	0.0195 (6)
H3	0.6361	0.1358	0.2225	0.023*
C4	0.5172 (3)	0.0454 (3)	0.14858 (15)	0.0208 (6)
H4	0.5467	−0.0402	0.1594	0.025*
C5	0.4211 (3)	0.0678 (3)	0.09613 (15)	0.0196 (6)
H5	0.3850	−0.0020	0.0700	0.024*
C6	0.3776 (3)	0.1931 (3)	0.08186 (14)	0.0158 (6)
H6	0.3088	0.2085	0.0466	0.019*
C7	0.9024 (4)	0.2550 (3)	0.09935 (16)	0.0295 (7)
H7A	0.8182	0.3084	0.0840	0.044*
H7B	0.8824	0.1643	0.0887	0.044*
H7C	0.9950	0.2827	0.0771	0.044*
C8	1.0302 (4)	0.2023 (3)	0.19757 (16)	0.0182 (7)
C9	1.0474 (3)	0.2317 (3)	0.27057 (14)	0.0154 (6)
C10	1.1650 (4)	0.1834 (3)	0.30627 (15)	0.0209 (6)
H10	1.2384	0.1302	0.2856	0.025*
C11	1.1758 (4)	0.2136 (3)	0.37360 (17)	0.0266 (7)
H11	1.2564	0.1803	0.3995	0.032*
C12	1.0684 (4)	0.2923 (3)	0.40256 (17)	0.0239 (7)
H12	1.0752	0.3138	0.4484	0.029*
C13	0.9520 (4)	0.3391 (3)	0.36472 (15)	0.0177 (6)
H13	0.8777	0.3932	0.3842	0.021*

	U11	U22	U33	U12	U13	U23
Sn1	0.01237 (8)	0.01123 (8)	0.01245 (8)	0.00035 (11)	−0.00144 (7)	−0.00058 (8)
Cl4	0.0168 (3)	0.0182 (3)	0.0195 (3)	−0.0011 (4)	0.0035 (2)	−0.0029 (3)
Cl3	0.0173 (3)	0.0198 (3)	0.0170 (3)	0.0010 (3)	0.0027 (3)	0.0005 (3)
Cl2	0.0263 (4)	0.0115 (3)	0.0270 (4)	0.0001 (3)	0.0020 (4)	−0.0006 (3)
Cl1	0.0186 (3)	0.0253 (4)	0.0173 (3)	0.0008 (3)	−0.0061 (3)	−0.0007 (3)
O1	0.0159 (8)	0.0182 (8)	0.0148 (8)	−0.0015 (12)	−0.0046 (7)	0.0011 (10)
O2	0.0170 (10)	0.0324 (11)	0.0156 (10)	0.0063 (10)	−0.0037 (9)	−0.0041 (9)
O3	0.0186 (11)	0.0297 (11)	0.0123 (9)	0.0005 (10)	−0.0002 (9)	−0.0031 (8)
O4	0.0294 (12)	0.0277 (10)	0.0242 (11)	0.0063 (12)	0.0070 (11)	−0.0067 (9)
N1	0.0132 (12)	0.0110 (10)	0.0139 (12)	0.0013 (10)	0.0015 (10)	0.0005 (8)
N2	0.0097 (12)	0.0163 (12)	0.0184 (13)	0.0012 (10)	−0.0026 (11)	0.0034 (10)
C1	0.0101 (13)	0.0242 (14)	0.0123 (12)	0.0042 (12)	0.0038 (11)	−0.0027 (11)
C2	0.0138 (13)	0.0190 (13)	0.0115 (13)	0.0018 (12)	0.0022 (11)	0.0021 (10)
C3	0.0210 (15)	0.0220 (14)	0.0155 (14)	0.0036 (13)	0.0025 (12)	0.0055 (11)
C4	0.0220 (15)	0.0150 (12)	0.0253 (16)	0.0023 (12)	0.0100 (13)	0.0063 (11)
C5	0.0212 (14)	0.0132 (12)	0.0245 (14)	−0.0020 (12)	0.0076 (14)	−0.0009 (11)
C6	0.0153 (13)	0.0151 (12)	0.0170 (14)	−0.0025 (12)	0.0034 (12)	−0.0015 (10)
C7	0.0268 (17)	0.0482 (19)	0.0134 (14)	0.0025 (18)	−0.0033 (17)	−0.0023 (15)
C8	0.0177 (15)	0.0183 (14)	0.0186 (16)	−0.0025 (13)	0.0012 (14)	−0.0014 (12)
C9	0.0145 (13)	0.0136 (12)	0.0181 (14)	−0.0013 (11)	0.0008 (12)	0.0009 (10)
C10	0.0172 (14)	0.0204 (14)	0.0253 (16)	0.0060 (12)	−0.0009 (14)	−0.0009 (12)
C11	0.0224 (16)	0.0333 (17)	0.0241 (16)	0.0063 (15)	−0.0067 (15)	0.0012 (14)
C12	0.0242 (16)	0.0292 (15)	0.0183 (14)	0.0027 (14)	−0.0047 (15)	−0.0018 (14)
C13	0.0184 (14)	0.0180 (13)	0.0165 (14)	0.0019 (12)	−0.0012 (12)	−0.0015 (11)

Sn1—O1	2.0868 (16)	C3—H3	0.9500
Sn1—N1	2.211 (2)	C4—C5	1.376 (4)
Sn1—Cl2	2.3647 (6)	C4—H4	0.9500
Sn1—Cl1	2.3687 (7)	C5—C6	1.384 (4)
Sn1—Cl4	2.4167 (6)	C5—H5	0.9500
Sn1—Cl3	2.4325 (7)	C6—H6	0.9500
O1—C1	1.291 (3)	C7—H7A	0.9800
O2—C1	1.222 (3)	C7—H7B	0.9800
O3—C8	1.320 (4)	C7—H7C	0.9800
O3—C7	1.454 (4)	C8—C9	1.506 (4)
O4—C8	1.199 (4)	C9—C10	1.363 (4)
N1—C2	1.341 (4)	C10—C11	1.392 (4)
N1—C6	1.337 (3)	C10—H10	0.9500
N2—C13	1.339 (4)	C11—C12	1.384 (5)
N2—C9	1.348 (4)	C11—H11	0.9500
N2—H2	0.88 (2)	C12—C13	1.373 (4)
C1—C2	1.516 (4)	C12—H12	0.9500
C2—C3	1.379 (4)	C13—H13	0.9500
C3—C4	1.391 (4)
O1—Sn1—N1	76.42 (9)	C5—C4—H4	120.2
O1—Sn1—Cl2	89.93 (7)	C3—C4—H4	120.2
N1—Sn1—Cl2	165.94 (7)	C4—C5—C6	119.3 (3)
O1—Sn1—Cl1	171.19 (7)	C4—C5—H5	120.3
N1—Sn1—Cl1	94.88 (6)	C6—C5—H5	120.3
Cl2—Sn1—Cl1	98.83 (3)	N1—C6—C5	121.0 (3)
O1—Sn1—Cl4	86.78 (5)	N1—C6—H6	119.5
N1—Sn1—Cl4	88.02 (6)	C5—C6—H6	119.5
Cl2—Sn1—Cl4	94.67 (3)	O3—C7—H7A	109.5
Cl1—Sn1—Cl4	91.57 (2)	O3—C7—H7B	109.5
O1—Sn1—Cl3	88.58 (5)	H7A—C7—H7B	109.5
N1—Sn1—Cl3	84.67 (6)	O3—C7—H7C	109.5
Cl2—Sn1—Cl3	91.72 (3)	H7A—C7—H7C	109.5
Cl1—Sn1—Cl3	92.04 (2)	H7B—C7—H7C	109.5
Cl4—Sn1—Cl3	172.10 (3)	O4—C8—O3	126.9 (3)
C1—O1—Sn1	118.83 (19)	O4—C8—C9	121.7 (3)
C8—O3—C7	115.1 (2)	O3—C8—C9	111.3 (3)
C2—N1—C6	119.9 (2)	N2—C9—C10	120.3 (3)
C2—N1—Sn1	113.08 (18)	N2—C9—C8	118.6 (3)
C6—N1—Sn1	126.95 (19)	C10—C9—C8	121.1 (3)
C13—N2—C9	122.2 (3)	C9—C10—C11	118.8 (3)
C13—N2—H2	116 (2)	C9—C10—H10	120.6
C9—N2—H2	122 (2)	C11—C10—H10	120.6
O2—C1—O1	124.0 (3)	C10—C11—C12	119.6 (3)
O2—C1—C2	119.9 (2)	C10—C11—H11	120.2
O1—C1—C2	116.0 (2)	C12—C11—H11	120.2
N1—C2—C3	122.1 (3)	C13—C12—C11	119.7 (3)
N1—C2—C1	115.5 (2)	C13—C12—H12	120.1
C3—C2—C1	122.4 (3)	C11—C12—H12	120.1
C2—C3—C4	118.1 (3)	N2—C13—C12	119.4 (3)
C2—C3—H3	121.0	N2—C13—H13	120.3
C4—C3—H3	121.0	C12—C13—H13	120.3
C5—C4—C3	119.5 (3)
N1—Sn1—O1—C1	−3.82 (19)	O1—C1—C2—C3	174.6 (3)
Cl2—Sn1—O1—C1	179.60 (18)	N1—C2—C3—C4	1.8 (4)
Cl4—Sn1—O1—C1	84.92 (18)	C1—C2—C3—C4	−175.4 (3)
Cl3—Sn1—O1—C1	−88.68 (18)	C2—C3—C4—C5	−0.9 (4)
O1—Sn1—N1—C2	2.07 (18)	C3—C4—C5—C6	−1.0 (4)
Cl2—Sn1—N1—C2	16.3 (4)	C2—N1—C6—C5	−1.1 (4)
Cl1—Sn1—N1—C2	−176.51 (18)	Sn1—N1—C6—C5	175.4 (2)
Cl4—Sn1—N1—C2	−85.10 (19)	C4—C5—C6—N1	2.0 (4)
Cl3—Sn1—N1—C2	91.89 (19)	C7—O3—C8—O4	−4.7 (5)
O1—Sn1—N1—C6	−174.6 (3)	C7—O3—C8—C9	175.2 (3)
Cl2—Sn1—N1—C6	−160.4 (2)	C13—N2—C9—C10	0.1 (4)
Cl1—Sn1—N1—C6	6.8 (2)	C13—N2—C9—C8	−179.6 (2)
Cl4—Sn1—N1—C6	98.3 (2)	O4—C8—C9—N2	−173.4 (3)
Cl3—Sn1—N1—C6	−84.8 (2)	O3—C8—C9—N2	6.7 (4)
Sn1—O1—C1—O2	−175.6 (2)	O4—C8—C9—C10	7.0 (5)
Sn1—O1—C1—C2	4.8 (3)	O3—C8—C9—C10	−173.0 (3)
C6—N1—C2—C3	−0.9 (4)	N2—C9—C10—C11	0.4 (4)
Sn1—N1—C2—C3	−177.8 (2)	C8—C9—C10—C11	180.0 (3)
C6—N1—C2—C1	176.5 (2)	C9—C10—C11—C12	−0.6 (5)
Sn1—N1—C2—C1	−0.4 (3)	C10—C11—C12—C13	0.4 (5)
O2—C1—C2—N1	177.7 (2)	C9—N2—C13—C12	−0.3 (4)
O1—C1—C2—N1	−2.7 (4)	C11—C12—C13—N2	0.0 (5)
O2—C1—C2—C3	−5.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88 (3)	1.89 (1)	2.745 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.88 (3)	1.89 (1)	2.745 (3)	166 (3)