2-(Ethoxy-carbon-yl)quinolinium butyl-trichlorido(quinoline-2-carboxyl-ato-κN,O)stannate(IV).

In the title compound, (C(12)H(12)NO(2))[Sn(C(4)H(9))(C(10)H(6)NO(2))Cl(3)], the Sn atom is coordinated by one O and one N atom of a quinolinium-2-carboxyl-ate anion, three Cl atoms and one butyl ligand within a distorted octa-hedron. Three C atoms of the butyl ligand are disordered and were refined using a split model; the site occupancies are 0.57 and 0.43. The NH group of the cation is involved in inter-molecular N-H⋯O hydrogen bonding.

Related literature

For related literature, see: Xie et al. (1991 ▶); Ma et al. (2006 ▶).

Experimental

Crystal data

(C12H12NO2)[n class="Chemical">Sn(C4H9)(C10H6NO2)Cl3]

M = 656.54

Monoclinic,

a = 13.6828 (18) Å

b = 11.0449 (15) Å

c = 18.598 (2) Å

β = 93.898 (2)°

V = 2804.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.23 mm−1

T = 293 (2) K

0.43 × 0.25 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.620, T max = 0.876

13504 measured reflections

4942 independent reflections

2884 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.00

4942 reflections

328 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067566/nc2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067566/nc2083Isup2.hkl

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

(C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]	F000 = 1320
Mr = 656.54	Dx = 1.555 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 13.6828 (18) Å	Cell parameters from 2742 reflections
b = 11.0449 (15) Å	θ = 2.2–20.4º
c = 18.598 (2) Å	µ = 1.23 mm−1
β = 93.898 (2)º	T = 293 (2) K
V = 2804.1 (6) Å3	Block, colourless
Z = 4	0.43 × 0.25 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	4942 independent reflections
Radiation source: fine-focus sealed tube	2884 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.050
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→12
Tmin = 0.620, Tmax = 0.877	k = −13→13
13504 measured reflections	l = −18→22

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.064P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4942 reflections	Δρmax = 0.64 e Å−3
328 parameters	Δρmin = −0.41 e Å−3
15 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.69831 (3)	0.03081 (4)	0.28168 (2)	0.04929 (18)
Cl1	0.74131 (13)	−0.15041 (15)	0.35719 (8)	0.0612 (5)
Cl2	0.82158 (17)	−0.01177 (16)	0.19623 (10)	0.0823 (7)
Cl3	0.65882 (15)	0.23171 (16)	0.23224 (10)	0.0769 (6)
O1	0.8168 (3)	0.1091 (4)	0.3402 (2)	0.0581 (12)
O2	0.8843 (4)	0.1604 (5)	0.4467 (3)	0.0805 (15)
N1	0.6386 (4)	0.1089 (4)	0.3890 (2)	0.0458 (12)
C1	0.8125 (5)	0.1382 (5)	0.4063 (4)	0.0512 (16)
C2	0.7123 (5)	0.1434 (5)	0.4343 (3)	0.0470 (15)
C3	0.6989 (6)	0.1831 (6)	0.5037 (3)	0.0617 (18)
H3	0.7526	0.2064	0.5339	0.074*
C4	0.6076 (6)	0.1880 (6)	0.5275 (4)	0.072 (2)
H4	0.5983	0.2139	0.5742	0.087*
C5	0.5276 (5)	0.1540 (6)	0.4815 (4)	0.0591 (18)
C6	0.5443 (5)	0.1167 (5)	0.4111 (3)	0.0497 (16)
C7	0.4649 (5)	0.0865 (7)	0.3630 (4)	0.076 (2)
H7	0.4755	0.0634	0.3161	0.092*
C8	0.3722 (6)	0.0909 (8)	0.3852 (5)	0.093 (3)
H8	0.3195	0.0703	0.3533	0.112*
C9	0.3554 (7)	0.1265 (8)	0.4561 (6)	0.093 (3)
H9	0.2921	0.1281	0.4714	0.111*
C10	0.4302 (7)	0.1574 (7)	0.5005 (5)	0.082 (3)
H10	0.4178	0.1827	0.5468	0.099*
C11	0.5827 (6)	−0.0718 (7)	0.2273 (4)	0.093 (3)
H11A	0.6106	−0.1407	0.2037	0.111*	0.57
H11B	0.5396	−0.1023	0.2625	0.111*	0.57
H11C	0.6017	−0.1564	0.2288	0.111*	0.43
H11D	0.5249	−0.0640	0.2544	0.111*	0.43
C12	0.5211 (17)	0.0064 (16)	0.1694 (10)	0.120 (6)*	0.57
H12A	0.4823	0.0644	0.1943	0.144*	0.57
H12B	0.5659	0.0516	0.1414	0.144*	0.57
C13	0.4535 (16)	−0.0666 (17)	0.1185 (10)	0.144 (7)*	0.57
H13A	0.3999	−0.1010	0.1433	0.173*	0.57
H13B	0.4887	−0.1313	0.0962	0.173*	0.57
C14	0.4166 (18)	0.0265 (18)	0.0631 (12)	0.148 (9)*	0.57
H14A	0.3730	−0.0118	0.0274	0.222*	0.57
H14B	0.4712	0.0606	0.0402	0.222*	0.57
H14C	0.3824	0.0895	0.0865	0.222*	0.57
C12'	0.553 (2)	−0.038 (3)	0.1457 (10)	0.147 (12)*	0.43
H12C	0.5956	0.0233	0.1271	0.176*	0.43
H12D	0.5502	−0.1082	0.1143	0.176*	0.43
C13'	0.451 (2)	0.011 (3)	0.1610 (18)	0.196 (16)*	0.43
H13C	0.4580	0.0926	0.1803	0.235*	0.43
H13D	0.4235	−0.0390	0.1974	0.235*	0.43
C14'	0.379 (2)	0.014 (3)	0.0927 (17)	0.155 (13)*	0.43
H14D	0.3172	0.0466	0.1048	0.232*	0.43
H14E	0.3694	−0.0671	0.0746	0.232*	0.43
H14F	0.4057	0.0633	0.0564	0.232*	0.43
O3	1.0771 (3)	0.3148 (4)	0.5369 (2)	0.0624 (12)
O4	1.0959 (3)	0.1229 (4)	0.4993 (2)	0.0598 (12)
N2	0.9935 (4)	0.0470 (4)	0.6118 (2)	0.0461 (12)
H2	1.0216	−0.0030	0.5844	0.055*
C15	1.0645 (5)	0.1969 (6)	0.5387 (3)	0.0506 (16)
C16	1.0041 (4)	0.1641 (5)	0.5998 (3)	0.0429 (14)
C17	0.9592 (5)	0.2459 (6)	0.6425 (3)	0.0542 (17)
H17	0.9642	0.3284	0.6335	0.058 (18)*
C18	0.9077 (5)	0.2060 (6)	0.6975 (3)	0.0593 (18)
H18	0.8796	0.2622	0.7272	0.07 (2)*
C19	0.8962 (5)	0.0835 (5)	0.7110 (3)	0.0487 (15)
C20	0.9409 (5)	0.0006 (5)	0.6651 (3)	0.0473 (16)
C21	0.9317 (5)	−0.1241 (6)	0.6754 (3)	0.0571 (18)
H21	0.9631	−0.1785	0.6465	0.07 (2)*
C22	0.8756 (5)	−0.1650 (7)	0.7282 (4)	0.068 (2)
H22	0.8660	−0.2477	0.7337	0.08 (2)*
C23	0.8330 (6)	−0.0833 (7)	0.7743 (4)	0.072 (2)
H23	0.7978	−0.1129	0.8116	0.07 (2)*
C24	0.8416 (5)	0.0365 (7)	0.7658 (4)	0.067 (2)
H24	0.8115	0.0890	0.7966	0.10 (3)*
C25	1.1392 (6)	0.3627 (7)	0.4834 (4)	0.084 (2)
H25A	1.1096	0.3482	0.4353	0.101*
H25B	1.2028	0.3236	0.4876	0.101*
C26	1.1503 (7)	0.4927 (7)	0.4965 (5)	0.107 (3)
H26A	1.0869	0.5301	0.4945	0.161*
H26B	1.1884	0.5276	0.4603	0.161*
H26C	1.1829	0.5056	0.5432	0.161*

	U11	U22	U33	U12	U13	U23
Sn1	0.0565 (3)	0.0507 (3)	0.0415 (3)	0.0008 (2)	0.00965 (19)	−0.0027 (2)
Cl1	0.0690 (12)	0.0592 (10)	0.0573 (10)	0.0150 (9)	0.0176 (8)	0.0050 (8)
Cl2	0.1224 (18)	0.0624 (11)	0.0690 (11)	0.0002 (11)	0.0563 (12)	−0.0073 (9)
Cl3	0.0952 (16)	0.0634 (11)	0.0731 (12)	0.0124 (11)	0.0122 (10)	0.0132 (9)
O1	0.048 (3)	0.071 (3)	0.058 (3)	0.000 (2)	0.015 (2)	−0.012 (2)
O2	0.053 (3)	0.109 (4)	0.079 (3)	−0.004 (3)	−0.007 (3)	−0.020 (3)
N1	0.042 (3)	0.049 (3)	0.047 (3)	0.009 (3)	0.008 (2)	−0.005 (2)
C1	0.047 (4)	0.049 (4)	0.058 (4)	0.001 (3)	0.008 (3)	−0.004 (3)
C2	0.050 (4)	0.046 (4)	0.046 (4)	0.004 (3)	0.008 (3)	−0.004 (3)
C3	0.073 (5)	0.066 (5)	0.046 (4)	0.000 (4)	0.005 (4)	−0.009 (3)
C4	0.098 (7)	0.067 (5)	0.055 (4)	0.011 (5)	0.023 (5)	−0.017 (4)
C5	0.065 (5)	0.053 (4)	0.063 (4)	0.016 (4)	0.031 (4)	0.004 (3)
C6	0.047 (4)	0.053 (4)	0.052 (4)	0.009 (3)	0.017 (3)	0.009 (3)
C7	0.052 (5)	0.106 (6)	0.072 (5)	0.000 (5)	0.010 (4)	0.009 (4)
C8	0.042 (5)	0.129 (7)	0.107 (7)	0.008 (5)	0.002 (5)	0.038 (6)
C9	0.058 (6)	0.096 (7)	0.128 (8)	0.024 (5)	0.044 (6)	0.030 (6)
C10	0.080 (7)	0.068 (5)	0.105 (7)	0.027 (5)	0.047 (6)	0.016 (5)
C11	0.098 (7)	0.083 (5)	0.093 (6)	−0.010 (5)	−0.028 (5)	−0.015 (5)
O3	0.075 (3)	0.054 (3)	0.061 (3)	−0.003 (3)	0.027 (2)	0.011 (2)
O4	0.065 (3)	0.069 (3)	0.047 (3)	0.000 (3)	0.012 (2)	−0.009 (2)
N2	0.048 (3)	0.049 (3)	0.042 (3)	0.002 (3)	0.006 (2)	−0.004 (2)
C15	0.043 (4)	0.064 (5)	0.045 (4)	−0.004 (3)	0.002 (3)	0.006 (3)
C16	0.037 (4)	0.044 (4)	0.048 (4)	−0.001 (3)	0.007 (3)	0.004 (3)
C17	0.056 (4)	0.044 (4)	0.064 (4)	−0.001 (3)	0.020 (3)	0.007 (3)
C18	0.071 (5)	0.048 (4)	0.062 (4)	0.006 (4)	0.028 (4)	−0.001 (3)
C19	0.053 (4)	0.044 (4)	0.050 (4)	0.001 (3)	0.011 (3)	0.000 (3)
C20	0.049 (4)	0.048 (4)	0.045 (4)	−0.002 (3)	0.004 (3)	0.007 (3)
C21	0.070 (5)	0.044 (4)	0.057 (4)	−0.003 (4)	0.005 (4)	−0.003 (3)
C22	0.078 (6)	0.057 (5)	0.069 (5)	−0.009 (4)	0.003 (4)	0.012 (4)
C23	0.088 (6)	0.070 (5)	0.060 (5)	−0.006 (5)	0.023 (4)	0.018 (4)
C24	0.074 (5)	0.064 (5)	0.066 (5)	0.001 (4)	0.027 (4)	0.006 (4)
C25	0.100 (7)	0.072 (5)	0.087 (6)	−0.021 (5)	0.045 (5)	0.012 (4)
C26	0.127 (9)	0.102 (7)	0.098 (6)	−0.028 (6)	0.042 (6)	0.026 (5)

Sn1—O1	2.079 (4)	C14—H14B	0.9600
Sn1—C11	2.142 (7)	C14—H14C	0.9600
Sn1—N1	2.371 (4)	C12'—C13'	1.547 (17)
Sn1—Cl2	2.4405 (18)	C12'—H12C	0.9700
Sn1—Cl3	2.4482 (18)	C12'—H12D	0.9700
Sn1—Cl1	2.4924 (16)	C13'—C14'	1.555 (17)
O1—C1	1.275 (7)	C13'—H13C	0.9700
O2—C1	1.221 (7)	C13'—H13D	0.9700
N1—C2	1.325 (7)	C14'—H14D	0.9600
N1—C6	1.383 (7)	C14'—H14E	0.9600
C1—C2	1.500 (8)	C14'—H14F	0.9600
C2—C3	1.386 (8)	O3—C15	1.315 (7)
C3—C4	1.355 (9)	O3—C25	1.452 (7)
C3—H3	0.9300	O4—C15	1.197 (7)
C4—C5	1.394 (10)	N2—C16	1.322 (7)
C4—H4	0.9300	N2—C20	1.363 (7)
C5—C10	1.403 (10)	N2—H2	0.8600
C5—C6	1.407 (8)	C15—C16	1.494 (8)
C6—C7	1.398 (9)	C16—C17	1.375 (8)
C7—C8	1.361 (10)	C17—C18	1.355 (8)
C7—H7	0.9300	C17—H17	0.9298
C8—C9	1.411 (11)	C18—C19	1.387 (8)
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.316 (11)	C19—C24	1.403 (8)
C9—H9	0.9300	C19—C20	1.419 (8)
C10—H10	0.9300	C20—C21	1.397 (8)
C11—C12	1.579 (13)	C21—C22	1.364 (8)
C11—C12'	1.587 (16)	C21—H21	0.9305
C11—H11A	0.9700	C22—C23	1.398 (9)
C11—H11B	0.9700	C22—H22	0.9295
C11—H11C	0.9700	C23—C24	1.339 (9)
C11—H11D	0.9700	C23—H23	0.9303
C12—C13	1.511 (14)	C24—H24	0.9306
C12—H12A	0.9700	C25—C26	1.463 (9)
C12—H12B	0.9700	C25—H25A	0.9699
C13—C14	1.518 (15)	C25—H25B	0.9699
C13—H13A	0.9700	C26—H26A	0.9600
C13—H13B	0.9700	C26—H26B	0.9600
C14—H14A	0.9600	C26—H26C	0.9600
O1—Sn1—C11	172.6 (2)	C14—C13—H13A	111.2
O1—Sn1—N1	73.06 (16)	C12—C13—H13B	111.2
C11—Sn1—N1	107.7 (3)	C14—C13—H13B	111.2
O1—Sn1—Cl2	82.66 (12)	H13A—C13—H13B	109.1
C11—Sn1—Cl2	96.4 (3)	C13—C14—H14A	109.5
N1—Sn1—Cl2	155.72 (13)	C13—C14—H14B	109.5
O1—Sn1—Cl3	87.93 (13)	H14A—C14—H14B	109.5
C11—Sn1—Cl3	99.5 (2)	C13—C14—H14C	109.5
N1—Sn1—Cl3	84.64 (12)	H14A—C14—H14C	109.5
Cl2—Sn1—Cl3	94.28 (6)	H14B—C14—H14C	109.5
O1—Sn1—Cl1	83.87 (13)	C13'—C12'—C11	94.6 (19)
C11—Sn1—Cl1	88.8 (2)	C13'—C12'—H12C	112.8
N1—Sn1—Cl1	84.22 (12)	C11—C12'—H12C	112.8
Cl2—Sn1—Cl1	93.73 (6)	C13'—C12'—H12D	112.8
Cl3—Sn1—Cl1	167.71 (6)	C11—C12'—H12D	112.8
C1—O1—Sn1	121.6 (4)	H12C—C12'—H12D	110.3
C2—N1—C6	118.7 (5)	C12'—C13'—C14'	113 (3)
C2—N1—Sn1	110.4 (4)	C12'—C13'—H13C	109.0
C6—N1—Sn1	130.8 (4)	C14'—C13'—H13C	109.0
O2—C1—O1	123.7 (6)	C12'—C13'—H13D	109.0
O2—C1—C2	119.7 (6)	C14'—C13'—H13D	109.0
O1—C1—C2	116.6 (6)	H13C—C13'—H13D	107.8
N1—C2—C3	122.6 (6)	C13'—C14'—H14D	109.5
N1—C2—C1	116.2 (5)	C13'—C14'—H14E	109.5
C3—C2—C1	121.2 (6)	H14D—C14'—H14E	109.5
C4—C3—C2	120.0 (7)	C13'—C14'—H14F	109.5
C4—C3—H3	120.0	H14D—C14'—H14F	109.5
C2—C3—H3	120.0	H14E—C14'—H14F	109.5
C3—C4—C5	119.4 (6)	C15—O3—C25	117.5 (5)
C3—C4—H4	120.3	C16—N2—C20	124.1 (5)
C5—C4—H4	120.3	C16—N2—H2	118.0
C4—C5—C10	123.9 (7)	C20—N2—H2	118.0
C4—C5—C6	118.8 (6)	O4—C15—O3	127.4 (6)
C10—C5—C6	117.3 (7)	O4—C15—C16	122.7 (6)
N1—C6—C7	119.7 (6)	O3—C15—C16	109.9 (6)
N1—C6—C5	120.5 (6)	N2—C16—C17	119.1 (5)
C7—C6—C5	119.8 (6)	N2—C16—C15	116.0 (5)
C8—C7—C6	119.8 (7)	C17—C16—C15	124.9 (6)
C8—C7—H7	120.1	C18—C17—C16	119.9 (6)
C6—C7—H7	120.1	C18—C17—H17	120.2
C7—C8—C9	120.5 (8)	C16—C17—H17	119.9
C7—C8—H8	119.8	C17—C18—C19	121.7 (6)
C9—C8—H8	119.8	C17—C18—H18	119.1
C10—C9—C8	119.4 (8)	C19—C18—H18	119.2
C10—C9—H9	120.3	C18—C19—C24	124.4 (6)
C8—C9—H9	120.3	C18—C19—C20	117.5 (6)
C9—C10—C5	123.1 (8)	C24—C19—C20	118.1 (6)
C9—C10—H10	118.4	N2—C20—C21	121.8 (6)
C5—C10—H10	118.4	N2—C20—C19	117.7 (5)
C12—C11—Sn1	112.1 (8)	C21—C20—C19	120.4 (6)
C12'—C11—Sn1	117.2 (12)	C22—C21—C20	119.1 (6)
C12—C11—H11A	109.2	C22—C21—H21	120.5
C12'—C11—H11A	80.4	C20—C21—H21	120.5
Sn1—C11—H11A	109.2	C21—C22—C23	120.4 (7)
C12—C11—H11B	109.2	C21—C22—H22	119.7
C12'—C11—H11B	126.9	C23—C22—H22	119.9
Sn1—C11—H11B	109.2	C24—C23—C22	121.5 (7)
H11A—C11—H11B	107.9	C24—C23—H23	119.3
C12—C11—H11C	132.5	C22—C23—H23	119.2
C12'—C11—H11C	107.6	C23—C24—C19	120.4 (7)
Sn1—C11—H11C	108.0	C23—C24—H24	119.8
H11B—C11—H11C	79.6	C19—C24—H24	119.8
C12—C11—H11D	83.6	O3—C25—C26	107.6 (6)
C12'—C11—H11D	108.3	O3—C25—H25A	110.2
Sn1—C11—H11D	108.0	C26—C25—H25A	110.3
H11A—C11—H11D	131.6	O3—C25—H25B	110.3
H11C—C11—H11D	107.3	C26—C25—H25B	110.0
C13—C12—C11	114.3 (14)	H25A—C25—H25B	108.5
C13—C12—H12A	108.7	C25—C26—H26A	109.5
C11—C12—H12A	108.7	C25—C26—H26B	109.5
C13—C12—H12B	108.7	H26A—C26—H26B	109.5
C11—C12—H12B	108.7	C25—C26—H26C	109.5
H12A—C12—H12B	107.6	H26A—C26—H26C	109.5
C12—C13—C14	103.0 (16)	H26B—C26—H26C	109.5
C12—C13—H13A	111.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.26	3.078 (7)	158
N2—H2···O4i	0.86	2.53	2.990 (6)	114

Sn1—O1	2.079 (4)
Sn1—C11	2.142 (7)
Sn1—N1	2.371 (4)
Sn1—Cl2	2.4405 (18)
Sn1—Cl3	2.4482 (18)
Sn1—Cl1	2.4924 (16)

O1—Sn1—C11	172.6 (2)
O1—Sn1—N1	73.06 (16)
C11—Sn1—N1	107.7 (3)
O1—Sn1—Cl2	82.66 (12)
C11—Sn1—Cl2	96.4 (3)
N1—Sn1—Cl2	155.72 (13)
O1—Sn1—Cl3	87.93 (13)
C11—Sn1—Cl3	99.5 (2)
N1—Sn1—Cl3	84.64 (12)
Cl2—Sn1—Cl3	94.28 (6)
O1—Sn1—Cl1	83.87 (13)
C11—Sn1—Cl1	88.8 (2)
N1—Sn1—Cl1	84.22 (12)
Cl2—Sn1—Cl1	93.73 (6)
Cl3—Sn1—Cl1	167.71 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.26	3.078 (7)	158
N2—H2⋯O4i	0.86	2.53	2.990 (6)	114

Symmetry code: (i) .