4-(Dimethyl-amino)-pyridinium tetra-chlorido(pyridine-2-carboxyl-ato-κ(2)N,O)stannate(IV).

The reaction of 4-(dimethyl-amino)-pyridine, picolinic acid and stannic chloride yields the title salt, (C(7)H(11)N(2))[SnCl(4)(C(6)H(4)NO(2))], in which the Sn(IV) atom is N,O-chelated by the picolinate ion 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 4-(dimethyl­amino)­pyridinium tetra­chlorido(quinoline-2-carboxyl­ato)stannate, see: Najafi et al. (2011 ▶).

Experimental

Crystal data

(C7H11N2)[SnCl4(C6H4NO2)]

M = 505.77

Triclinic,

a = 7.6658 (2) Å

b = 9.8948 (4) Å

c = 13.5722 (6) Å

α = 69.485 (4)°

β = 83.159 (3)°

γ = 67.900 (3)°

V = 893.25 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.04 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 = 0.580, T max = 0.686

12966 measured reflections

4109 independent reflections

3744 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.049

S = 1.02

4109 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.41 e Å−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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201968X/bt5909sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201968X/bt5909Isup2.hkl

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

(C7H11N2)[SnCl4(C6H4NO2)]	Z = 2
Mr = 505.77	F(000) = 496
Triclinic, P1	Dx = 1.880 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6658 (2) Å	Cell parameters from 8614 reflections
b = 9.8948 (4) Å	θ = 2.4–27.5°
c = 13.5722 (6) Å	µ = 2.04 mm−1
α = 69.485 (4)°	T = 100 K
β = 83.159 (3)°	Prism, colorless
γ = 67.900 (3)°	0.30 × 0.25 × 0.20 mm
V = 893.25 (6) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4109 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3744 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
Tmin = 0.580, Tmax = 0.686	l = −17→17
12966 measured reflections

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0217P)2 + 0.1127P] where P = (Fo2 + 2Fc2)/3
4109 reflections	(Δ/σ)max = 0.002
214 parameters	Δρmax = 0.61 e Å−3
1 restraint	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.471694 (16)	0.931155 (14)	0.787934 (10)	0.01225 (5)
Cl1	0.41910 (7)	1.16043 (5)	0.82535 (4)	0.01887 (11)
Cl2	0.63070 (7)	0.97801 (6)	0.62519 (4)	0.01884 (11)
Cl3	0.76267 (6)	0.79583 (6)	0.88640 (4)	0.01957 (11)
Cl4	0.16639 (6)	1.04910 (5)	0.70014 (4)	0.01687 (10)
O1	0.48413 (18)	0.72139 (15)	0.77597 (11)	0.0164 (3)
O2	0.3917 (2)	0.51987 (16)	0.84279 (12)	0.0231 (3)
N1	0.3269 (2)	0.83176 (18)	0.93069 (12)	0.0137 (3)
N2	0.6230 (2)	0.5870 (2)	0.61853 (14)	0.0184 (4)
H2	0.574 (3)	0.630 (3)	0.6665 (15)	0.038 (7)*
N3	0.8688 (2)	0.35910 (18)	0.40725 (13)	0.0153 (3)
C1	0.3977 (3)	0.6389 (2)	0.84580 (16)	0.0159 (4)
C2	0.3057 (3)	0.7014 (2)	0.93305 (15)	0.0155 (4)
C3	0.2055 (3)	0.6298 (2)	1.01141 (17)	0.0217 (5)
H3	0.1910	0.5382	1.0122	0.026*
C4	0.1268 (3)	0.6952 (3)	1.08887 (17)	0.0270 (5)
H4	0.0545	0.6500	1.1428	0.032*
C5	0.1535 (3)	0.8254 (3)	1.08742 (16)	0.0235 (5)
H5	0.1024	0.8694	1.1412	0.028*
C6	0.2552 (3)	0.8922 (2)	1.00731 (15)	0.0178 (4)
H6	0.2744	0.9819	1.0066	0.021*
C7	0.6389 (3)	0.4385 (2)	0.64189 (16)	0.0176 (4)
H7	0.5927	0.3883	0.7070	0.021*
C8	0.7198 (2)	0.3592 (2)	0.57414 (15)	0.0153 (4)
H8	0.7304	0.2546	0.5922	0.018*
C9	0.7888 (2)	0.4335 (2)	0.47584 (15)	0.0137 (4)
C10	0.7676 (3)	0.5896 (2)	0.45468 (16)	0.0159 (4)
H10	0.8102	0.6444	0.3900	0.019*
C11	0.6865 (3)	0.6614 (2)	0.52659 (17)	0.0183 (4)
H11	0.6745	0.7657	0.5117	0.022*
C12	0.8845 (3)	0.1993 (2)	0.42939 (17)	0.0213 (5)
H12A	0.9601	0.1329	0.4937	0.032*
H12B	0.9454	0.1647	0.3704	0.032*
H12C	0.7585	0.1933	0.4390	0.032*
C13	0.9392 (3)	0.4362 (2)	0.30663 (16)	0.0201 (4)
H13A	1.0157	0.4893	0.3186	0.030*
H13B	0.8327	0.5118	0.2599	0.030*
H13C	1.0164	0.3592	0.2741	0.030*

	U11	U22	U33	U12	U13	U23
Sn1	0.01423 (8)	0.01017 (8)	0.01266 (8)	−0.00471 (5)	0.00094 (5)	−0.00403 (5)
Cl1	0.0237 (2)	0.0125 (2)	0.0218 (3)	−0.00547 (19)	−0.00284 (19)	−0.0074 (2)
Cl2	0.0212 (2)	0.0168 (2)	0.0171 (3)	−0.00816 (19)	0.00602 (18)	−0.00436 (19)
Cl3	0.0165 (2)	0.0175 (2)	0.0221 (3)	−0.00282 (19)	−0.00390 (18)	−0.0058 (2)
Cl4	0.0166 (2)	0.0169 (2)	0.0167 (2)	−0.00586 (19)	−0.00196 (17)	−0.00459 (19)
O1	0.0222 (7)	0.0122 (7)	0.0173 (7)	−0.0088 (6)	0.0041 (5)	−0.0062 (6)
O2	0.0294 (8)	0.0166 (8)	0.0270 (9)	−0.0130 (6)	0.0004 (6)	−0.0063 (6)
N1	0.0137 (8)	0.0129 (8)	0.0121 (8)	−0.0034 (6)	−0.0013 (6)	−0.0025 (7)
N2	0.0170 (8)	0.0200 (9)	0.0193 (9)	−0.0035 (7)	−0.0013 (7)	−0.0105 (8)
N3	0.0178 (8)	0.0118 (8)	0.0167 (9)	−0.0054 (7)	0.0020 (6)	−0.0054 (7)
C1	0.0149 (9)	0.0134 (10)	0.0178 (10)	−0.0052 (8)	−0.0041 (7)	−0.0019 (8)
C2	0.0136 (9)	0.0131 (10)	0.0156 (10)	−0.0032 (8)	−0.0040 (7)	−0.0001 (8)
C3	0.0189 (10)	0.0203 (11)	0.0214 (11)	−0.0093 (8)	−0.0026 (8)	0.0020 (9)
C4	0.0186 (10)	0.0331 (13)	0.0181 (12)	−0.0088 (9)	0.0027 (8)	0.0032 (10)
C5	0.0190 (10)	0.0286 (12)	0.0143 (11)	−0.0009 (9)	−0.0011 (8)	−0.0050 (9)
C6	0.0168 (10)	0.0197 (11)	0.0133 (10)	−0.0028 (8)	−0.0017 (7)	−0.0047 (8)
C7	0.0144 (9)	0.0201 (11)	0.0168 (10)	−0.0071 (8)	−0.0009 (7)	−0.0031 (8)
C8	0.0138 (9)	0.0125 (10)	0.0177 (10)	−0.0052 (8)	−0.0010 (7)	−0.0018 (8)
C9	0.0105 (9)	0.0130 (10)	0.0165 (10)	−0.0035 (7)	−0.0027 (7)	−0.0036 (8)
C10	0.0174 (9)	0.0120 (10)	0.0179 (10)	−0.0060 (8)	−0.0029 (7)	−0.0027 (8)
C11	0.0177 (10)	0.0120 (10)	0.0244 (11)	−0.0036 (8)	−0.0062 (8)	−0.0048 (8)
C12	0.0227 (10)	0.0138 (10)	0.0289 (12)	−0.0058 (8)	0.0011 (9)	−0.0099 (9)
C13	0.0208 (10)	0.0208 (11)	0.0170 (11)	−0.0067 (9)	0.0030 (8)	−0.0059 (9)

Sn1—O1	2.1041 (13)	C4—C5	1.372 (3)
Sn1—N1	2.2194 (16)	C4—H4	0.9500
Sn1—Cl1	2.3743 (5)	C5—C6	1.381 (3)
Sn1—Cl2	2.3761 (5)	C5—H5	0.9500
Sn1—Cl3	2.4006 (5)	C6—H6	0.9500
Sn1—Cl4	2.4277 (5)	C7—C8	1.359 (3)
O1—C1	1.311 (2)	C7—H7	0.9500
O2—C1	1.210 (2)	C8—C9	1.427 (3)
N1—C6	1.339 (2)	C8—H8	0.9500
N1—C2	1.348 (3)	C9—C10	1.416 (3)
N2—C11	1.348 (3)	C10—C11	1.361 (3)
N2—C7	1.350 (3)	C10—H10	0.9500
N2—H2	0.874 (10)	C11—H11	0.9500
N3—C9	1.338 (2)	C12—H12A	0.9800
N3—C12	1.462 (3)	C12—H12B	0.9800
N3—C13	1.464 (2)	C12—H12C	0.9800
C1—C2	1.506 (3)	C13—H13A	0.9800
C2—C3	1.382 (3)	C13—H13B	0.9800
C3—C4	1.386 (3)	C13—H13C	0.9800
C3—H3	0.9500
O1—Sn1—N1	75.84 (6)	C5—C4—H4	120.1
O1—Sn1—Cl1	169.89 (4)	C3—C4—H4	120.1
N1—Sn1—Cl1	94.27 (4)	C4—C5—C6	119.6 (2)
O1—Sn1—Cl2	88.75 (4)	C4—C5—H5	120.2
N1—Sn1—Cl2	164.57 (4)	C6—C5—H5	120.2
Cl1—Sn1—Cl2	101.090 (18)	N1—C6—C5	120.7 (2)
O1—Sn1—Cl3	89.31 (4)	N1—C6—H6	119.6
N1—Sn1—Cl3	88.57 (4)	C5—C6—H6	119.6
Cl1—Sn1—Cl3	92.581 (18)	N2—C7—C8	121.32 (19)
Cl2—Sn1—Cl3	92.190 (18)	N2—C7—H7	119.3
O1—Sn1—Cl4	87.20 (4)	C8—C7—H7	119.3
N1—Sn1—Cl4	86.38 (4)	C7—C8—C9	119.91 (19)
Cl1—Sn1—Cl4	90.124 (17)	C7—C8—H8	120.0
Cl2—Sn1—Cl4	92.055 (17)	C9—C8—H8	120.0
Cl3—Sn1—Cl4	174.439 (17)	N3—C9—C10	121.88 (18)
C1—O1—Sn1	119.22 (12)	N3—C9—C8	121.49 (18)
C6—N1—C2	120.02 (17)	C10—C9—C8	116.63 (18)
C6—N1—Sn1	126.65 (14)	C11—C10—C9	120.29 (19)
C2—N1—Sn1	113.24 (12)	C11—C10—H10	119.9
C11—N2—C7	120.66 (18)	C9—C10—H10	119.9
C11—N2—H2	122.3 (18)	N2—C11—C10	121.18 (19)
C7—N2—H2	117.0 (18)	N2—C11—H11	119.4
C9—N3—C12	120.98 (17)	C10—C11—H11	119.4
C9—N3—C13	121.09 (17)	N3—C12—H12A	109.5
C12—N3—C13	117.91 (16)	N3—C12—H12B	109.5
O2—C1—O1	123.64 (18)	H12A—C12—H12B	109.5
O2—C1—C2	121.19 (18)	N3—C12—H12C	109.5
O1—C1—C2	115.16 (17)	H12A—C12—H12C	109.5
N1—C2—C3	121.61 (19)	H12B—C12—H12C	109.5
N1—C2—C1	116.16 (17)	N3—C13—H13A	109.5
C3—C2—C1	122.22 (19)	N3—C13—H13B	109.5
C2—C3—C4	118.2 (2)	H13A—C13—H13B	109.5
C2—C3—H3	120.9	N3—C13—H13C	109.5
C4—C3—H3	120.9	H13A—C13—H13C	109.5
C5—C4—C3	119.8 (2)	H13B—C13—H13C	109.5
N1—Sn1—O1—C1	4.83 (13)	O1—C1—C2—N1	−1.6 (2)
Cl1—Sn1—O1—C1	−7.3 (3)	O2—C1—C2—C3	−2.2 (3)
Cl2—Sn1—O1—C1	−174.26 (13)	O1—C1—C2—C3	178.52 (17)
Cl3—Sn1—O1—C1	93.53 (13)	N1—C2—C3—C4	−0.3 (3)
Cl4—Sn1—O1—C1	−82.14 (13)	C1—C2—C3—C4	179.61 (17)
O1—Sn1—N1—C6	178.01 (16)	C2—C3—C4—C5	−1.5 (3)
Cl1—Sn1—N1—C6	−4.12 (15)	C3—C4—C5—C6	1.5 (3)
Cl2—Sn1—N1—C6	−178.59 (11)	C2—N1—C6—C5	−2.2 (3)
Cl3—Sn1—N1—C6	88.36 (15)	Sn1—N1—C6—C5	174.16 (13)
Cl4—Sn1—N1—C6	−93.97 (15)	C4—C5—C6—N1	0.4 (3)
O1—Sn1—N1—C2	−5.40 (12)	C11—N2—C7—C8	0.3 (3)
Cl1—Sn1—N1—C2	172.47 (12)	N2—C7—C8—C9	−0.4 (3)
Cl2—Sn1—N1—C2	−2.0 (2)	C12—N3—C9—C10	−178.27 (17)
Cl3—Sn1—N1—C2	−95.05 (12)	C13—N3—C9—C10	0.2 (3)
Cl4—Sn1—N1—C2	82.62 (12)	C12—N3—C9—C8	1.5 (3)
Sn1—O1—C1—O2	177.24 (15)	C13—N3—C9—C8	−179.96 (16)
Sn1—O1—C1—C2	−3.5 (2)	C7—C8—C9—N3	−179.87 (17)
C6—N1—C2—C3	2.2 (3)	C7—C8—C9—C10	−0.1 (3)
Sn1—N1—C2—C3	−174.69 (14)	N3—C9—C10—C11	−179.60 (17)
C6—N1—C2—C1	−177.72 (16)	C8—C9—C10—C11	0.6 (3)
Sn1—N1—C2—C1	5.44 (19)	C7—N2—C11—C10	0.3 (3)
O2—C1—C2—N1	177.67 (17)	C9—C10—C11—N2	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.87 (1)	1.93 (1)	2.802 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.87 (1)	1.93 (1)	2.802 (2)	176 (2)