3-Meth-oxy-carbonyl-1-methyl-pyrazinium tetra-chlorido(pyrazine-2-carboxyl-ato-κN,O)stannate(IV).

In the reaction of pyrazine-2-carb-oxy-lic acid and stannic chloride in methanol, one equivalent of the carb-oxy-lic acid is methyl-ated at the 4-amino site and is also esterified, yielding the title salt, (C(7)H(9)N(2)O(2))[SnCl(4)(C(5)H(3)N(2)O(2))]. The Sn(IV) atom in the anion is N,O-chelated by a pyrazine-2-carboxyl-ate in a cis-SnNOCl(4) octa-hedral geometry.

Related literature

For related organotin structures, see: Ma et al. (2004 ▶).

Experimental

Crystal data

(C7H9N2O2)[SnCl4(C5H3N2O2)]

M = 536.75

Monoclinic,

a = 7.0655 (2) Å

b = 26.7603 (7) Å

c = 9.5220 (2) Å

β = 94.554 (2)°

V = 1794.69 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.05 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 = 0.579, T max = 0.685

8726 measured reflections

3964 independent reflections

3582 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.059

S = 1.02

3964 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.71 e Å−3

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/S1600536811001929/si2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001929/si2325Isup2.hkl

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

(C7H9N2O2)[SnCl4(C5H3N2O2)]	F(000) = 1048
Mr = 536.75	Dx = 1.987 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5671 reflections
a = 7.0655 (2) Å	θ = 2.3–29.2°
b = 26.7603 (7) Å	µ = 2.05 mm−1
c = 9.5220 (2) Å	T = 100 K
β = 94.554 (2)°	Prism, colorless
V = 1794.69 (8) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3964 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3582 reflections with I > 2σ(I)
Mirror	Rint = 0.024
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −19→33
Tmin = 0.579, Tmax = 0.685	l = −12→11
8726 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0273P)2 + 1.1852P] where P = (Fo2 + 2Fc2)/3
3964 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.60924 (2)	0.655455 (6)	0.329618 (16)	0.01294 (6)
Cl1	0.37306 (8)	0.67760 (2)	0.14686 (6)	0.01817 (13)
Cl2	0.86908 (9)	0.70312 (3)	0.26342 (7)	0.02392 (15)
Cl3	0.50421 (8)	0.72003 (2)	0.48125 (6)	0.01835 (13)
Cl4	0.70745 (9)	0.58382 (2)	0.20077 (6)	0.02003 (14)
O1	0.7650 (2)	0.62593 (7)	0.50542 (17)	0.0159 (4)
O2	0.7745 (3)	0.56931 (7)	0.67716 (18)	0.0218 (4)
O3	1.1503 (3)	0.55738 (7)	1.01670 (19)	0.0237 (4)
O4	1.4080 (3)	0.57009 (8)	0.89617 (19)	0.0265 (4)
N1	0.4045 (3)	0.60323 (8)	0.4241 (2)	0.0137 (4)
N2	0.2115 (3)	0.52822 (8)	0.5541 (2)	0.0189 (5)
N3	0.8601 (3)	0.67062 (8)	0.8236 (2)	0.0157 (4)
N4	1.2150 (3)	0.64576 (8)	0.7473 (2)	0.0194 (5)
C1	0.6920 (3)	0.59043 (9)	0.5772 (2)	0.0151 (5)
C2	0.4893 (3)	0.57708 (9)	0.5319 (2)	0.0135 (5)
C3	0.3911 (4)	0.53973 (9)	0.5957 (2)	0.0167 (5)
H3	0.4537	0.5217	0.6717	0.020*
C4	0.1292 (3)	0.55520 (10)	0.4485 (3)	0.0187 (5)
H4	0.0009	0.5483	0.4172	0.022*
C5	0.2236 (3)	0.59312 (10)	0.3823 (3)	0.0170 (5)
H5	0.1597	0.6117	0.3079	0.020*
C6	1.2439 (4)	0.51458 (11)	1.0871 (3)	0.0283 (6)
H6A	1.1620	0.5007	1.1558	0.042*
H6B	1.3646	0.5253	1.1357	0.042*
H6C	1.2680	0.4890	1.0172	0.042*
C7	1.2504 (4)	0.58058 (10)	0.9240 (3)	0.0190 (5)
C8	1.1371 (3)	0.62241 (10)	0.8531 (2)	0.0161 (5)
C9	0.9594 (3)	0.63438 (10)	0.8935 (3)	0.0171 (5)
H9	0.9082	0.6173	0.9693	0.021*
C10	0.9332 (4)	0.69445 (10)	0.7175 (3)	0.0178 (5)
H10	0.8632	0.7200	0.6675	0.021*
C11	1.1126 (4)	0.68141 (10)	0.6813 (3)	0.0201 (5)
H11	1.1643	0.6987	0.6060	0.024*
C12	0.6682 (3)	0.68313 (11)	0.8634 (3)	0.0225 (6)
H12A	0.6061	0.7056	0.7928	0.034*
H12B	0.6777	0.6996	0.9556	0.034*
H12C	0.5933	0.6525	0.8684	0.034*

	U11	U22	U33	U12	U13	U23
Sn1	0.01198 (9)	0.01295 (10)	0.01393 (9)	−0.00115 (6)	0.00119 (6)	0.00060 (6)
Cl1	0.0190 (3)	0.0184 (3)	0.0166 (3)	0.0002 (2)	−0.0016 (2)	0.0015 (2)
Cl2	0.0176 (3)	0.0224 (4)	0.0324 (3)	−0.0056 (3)	0.0063 (3)	0.0047 (3)
Cl3	0.0208 (3)	0.0170 (3)	0.0172 (3)	0.0022 (2)	0.0015 (2)	−0.0020 (2)
Cl4	0.0217 (3)	0.0188 (3)	0.0199 (3)	0.0023 (2)	0.0029 (2)	−0.0030 (2)
O1	0.0132 (8)	0.0157 (9)	0.0180 (8)	−0.0006 (7)	−0.0036 (7)	0.0014 (7)
O2	0.0225 (9)	0.0220 (11)	0.0200 (9)	−0.0004 (8)	−0.0048 (7)	0.0033 (8)
O3	0.0239 (10)	0.0209 (11)	0.0259 (10)	0.0029 (8)	−0.0005 (8)	0.0048 (8)
O4	0.0220 (10)	0.0319 (12)	0.0253 (10)	0.0089 (8)	0.0009 (8)	−0.0018 (8)
N1	0.0120 (9)	0.0124 (11)	0.0169 (10)	−0.0008 (8)	0.0017 (8)	−0.0009 (8)
N2	0.0182 (10)	0.0157 (12)	0.0230 (11)	−0.0018 (9)	0.0030 (9)	0.0006 (9)
N3	0.0156 (10)	0.0153 (11)	0.0159 (10)	−0.0013 (8)	−0.0009 (8)	−0.0031 (8)
N4	0.0159 (10)	0.0218 (13)	0.0204 (11)	−0.0029 (9)	0.0006 (9)	−0.0014 (9)
C1	0.0188 (12)	0.0119 (13)	0.0143 (11)	0.0015 (10)	−0.0010 (10)	−0.0027 (9)
C2	0.0158 (11)	0.0114 (12)	0.0135 (11)	0.0025 (9)	0.0022 (9)	−0.0007 (9)
C3	0.0223 (12)	0.0133 (13)	0.0147 (11)	0.0003 (10)	0.0025 (10)	−0.0008 (10)
C4	0.0133 (11)	0.0186 (14)	0.0243 (13)	−0.0015 (10)	0.0021 (10)	−0.0018 (11)
C5	0.0154 (11)	0.0171 (14)	0.0183 (12)	0.0007 (10)	0.0002 (10)	0.0006 (10)
C6	0.0344 (16)	0.0207 (16)	0.0282 (14)	0.0040 (12)	−0.0068 (12)	0.0027 (12)
C7	0.0194 (13)	0.0199 (14)	0.0172 (12)	−0.0016 (11)	−0.0025 (10)	−0.0052 (10)
C8	0.0164 (12)	0.0149 (13)	0.0165 (12)	−0.0015 (10)	−0.0012 (10)	−0.0036 (9)
C9	0.0182 (12)	0.0158 (13)	0.0168 (12)	−0.0006 (10)	−0.0010 (10)	−0.0013 (10)
C10	0.0198 (12)	0.0145 (13)	0.0187 (12)	−0.0020 (10)	−0.0019 (10)	−0.0008 (10)
C11	0.0214 (13)	0.0198 (15)	0.0191 (12)	−0.0054 (11)	0.0018 (10)	−0.0004 (11)
C12	0.0147 (12)	0.0246 (16)	0.0284 (14)	0.0036 (11)	0.0037 (11)	−0.0007 (12)

Sn1—O1	2.0843 (17)	N4—C8	1.340 (3)
Sn1—N1	2.2499 (19)	C1—C2	1.506 (3)
Sn1—Cl2	2.3619 (6)	C2—C3	1.384 (3)
Sn1—Cl1	2.3881 (6)	C3—H3	0.9500
Sn1—Cl3	2.4065 (6)	C4—C5	1.392 (4)
Sn1—Cl4	2.4076 (6)	C4—H4	0.9500
O1—C1	1.301 (3)	C5—H5	0.9500
O2—C1	1.215 (3)	C6—H6A	0.9800
O3—C7	1.328 (3)	C6—H6B	0.9800
O3—C6	1.459 (3)	C6—H6C	0.9800
O4—C7	1.199 (3)	C7—C8	1.504 (4)
N1—C5	1.336 (3)	C8—C9	1.380 (3)
N1—C2	1.343 (3)	C9—H9	0.9500
N2—C4	1.333 (3)	C10—C11	1.384 (4)
N2—C3	1.335 (3)	C10—H10	0.9500
N3—C10	1.333 (3)	C11—H11	0.9500
N3—C9	1.342 (3)	C12—H12A	0.9800
N3—C12	1.475 (3)	C12—H12B	0.9800
N4—C11	1.326 (3)	C12—H12C	0.9800
O1—Sn1—N1	76.03 (7)	N2—C4—C5	122.7 (2)
O1—Sn1—Cl2	92.70 (5)	N2—C4—H4	118.6
N1—Sn1—Cl2	168.60 (5)	C5—C4—H4	118.6
O1—Sn1—Cl1	166.67 (5)	N1—C5—C4	119.6 (2)
N1—Sn1—Cl1	90.65 (5)	N1—C5—H5	120.2
Cl2—Sn1—Cl1	100.63 (2)	C4—C5—H5	120.2
O1—Sn1—Cl3	87.62 (5)	O3—C6—H6A	109.5
N1—Sn1—Cl3	88.13 (5)	O3—C6—H6B	109.5
Cl2—Sn1—Cl3	93.19 (2)	H6A—C6—H6B	109.5
Cl1—Sn1—Cl3	91.61 (2)	O3—C6—H6C	109.5
O1—Sn1—Cl4	87.27 (5)	H6A—C6—H6C	109.5
N1—Sn1—Cl4	85.97 (5)	H6B—C6—H6C	109.5
Cl2—Sn1—Cl4	91.86 (2)	O4—C7—O3	126.2 (3)
Cl1—Sn1—Cl4	92.25 (2)	O4—C7—C8	123.1 (2)
Cl3—Sn1—Cl4	172.98 (2)	O3—C7—C8	110.7 (2)
C1—O1—Sn1	119.54 (15)	N4—C8—C9	122.6 (2)
C7—O3—C6	115.3 (2)	N4—C8—C7	116.6 (2)
C5—N1—C2	118.7 (2)	C9—C8—C7	120.8 (2)
C5—N1—Sn1	129.58 (17)	N3—C9—C8	118.7 (2)
C2—N1—Sn1	111.54 (15)	N3—C9—H9	120.6
C4—N2—C3	116.5 (2)	C8—C9—H9	120.6
C10—N3—C9	120.2 (2)	N3—C10—C11	119.1 (2)
C10—N3—C12	120.4 (2)	N3—C10—H10	120.5
C9—N3—C12	119.4 (2)	C11—C10—H10	120.5
C11—N4—C8	116.8 (2)	N4—C11—C10	122.6 (2)
O2—C1—O1	124.5 (2)	N4—C11—H11	118.7
O2—C1—C2	120.0 (2)	C10—C11—H11	118.7
O1—C1—C2	115.5 (2)	N3—C12—H12A	109.5
N1—C2—C3	120.2 (2)	N3—C12—H12B	109.5
N1—C2—C1	116.9 (2)	H12A—C12—H12B	109.5
C3—C2—C1	122.9 (2)	N3—C12—H12C	109.5
N2—C3—C2	122.3 (2)	H12A—C12—H12C	109.5
N2—C3—H3	118.9	H12B—C12—H12C	109.5
C2—C3—H3	118.9
N1—Sn1—O1—C1	6.32 (17)	O1—C1—C2—C3	179.1 (2)
Cl2—Sn1—O1—C1	−171.93 (17)	C4—N2—C3—C2	−1.1 (4)
Cl1—Sn1—O1—C1	8.0 (3)	N1—C2—C3—N2	0.0 (4)
Cl3—Sn1—O1—C1	94.98 (17)	C1—C2—C3—N2	−179.8 (2)
Cl4—Sn1—O1—C1	−80.20 (17)	C3—N2—C4—C5	0.8 (4)
O1—Sn1—N1—C5	178.9 (2)	C2—N1—C5—C4	−1.6 (4)
Cl2—Sn1—N1—C5	−172.28 (19)	Sn1—N1—C5—C4	173.07 (17)
Cl1—Sn1—N1—C5	−0.7 (2)	N2—C4—C5—N1	0.5 (4)
Cl3—Sn1—N1—C5	90.9 (2)	C6—O3—C7—O4	−1.4 (4)
Cl4—Sn1—N1—C5	−92.9 (2)	C6—O3—C7—C8	177.4 (2)
O1—Sn1—N1—C2	−6.18 (15)	C11—N4—C8—C9	−0.2 (4)
Cl2—Sn1—N1—C2	2.7 (4)	C11—N4—C8—C7	177.6 (2)
Cl1—Sn1—N1—C2	174.22 (15)	O4—C7—C8—N4	5.1 (4)
Cl3—Sn1—N1—C2	−94.20 (15)	O3—C7—C8—N4	−173.7 (2)
Cl4—Sn1—N1—C2	82.01 (15)	O4—C7—C8—C9	−177.1 (2)
Sn1—O1—C1—O2	176.53 (19)	O3—C7—C8—C9	4.1 (3)
Sn1—O1—C1—C2	−5.3 (3)	C10—N3—C9—C8	−0.1 (4)
C5—N1—C2—C3	1.4 (3)	C12—N3—C9—C8	178.7 (2)
Sn1—N1—C2—C3	−174.21 (18)	N4—C8—C9—N3	0.4 (4)
C5—N1—C2—C1	−178.8 (2)	C7—C8—C9—N3	−177.3 (2)
Sn1—N1—C2—C1	5.6 (3)	C9—N3—C10—C11	−0.3 (4)
O2—C1—C2—N1	177.5 (2)	C12—N3—C10—C11	−179.1 (2)
O1—C1—C2—N1	−0.7 (3)	C8—N4—C11—C10	−0.2 (4)
O2—C1—C2—C3	−2.7 (4)	N3—C10—C11—N4	0.5 (4)