2-(Methoxy-carbon-yl)quinolinium tetra-chlorido(quinoline-2-carboxyl-ato-κN,O)stannate(IV) methanol solvate.

In the title salt, (C(11)H(10)NO(2))[SnCl(4)(C(10)H(6)NO(2))]·CH(3)OH, the Sn atom is chelated by the quinolincarboxyl-ate unit and it exists in a distorted octa-hedral coordination geometry. The cation is linked to the solvent mol-ecule by an N-H⋯O hydrogen bond; the solvent mol-ecule is linked to the anion by an O-H⋯O hydrogen bond.

Related literature

For the structure of 2-(ethoxy­carbon­yl)quinolinium n-butyl­trichlorido(quinolin-2-carboxyl­ato)stannate(IV), see: Wang et al. (2008 ▶).

Experimental

Crystal data

(C11H10NO2)[SnCl4(C10H6NO2)]·CH4O

M = 652.89

Monoclinic,

a = 8.4109 (4) Å

b = 33.2728 (16) Å

c = 10.0241 (5) Å

β = 112.8616 (6)°

V = 2584.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.44 mm−1

T = 293 K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.633, T max = 0.813

24727 measured reflections

5924 independent reflections

5288 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.17

5924 reflections

317 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −1.15 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/S1600536810008561/bt5208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008561/bt5208Isup2.hkl

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

(C11H10NO2)[SnCl4(C10H6NO2)]·CH4O	F(000) = 1296
Mr = 652.89	Dx = 1.678 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9921 reflections
a = 8.4109 (4) Å	θ = 2.3–28.1°
b = 33.2728 (16) Å	µ = 1.44 mm−1
c = 10.0241 (5) Å	T = 293 K
β = 112.8616 (6)°	Wedge, colorless
V = 2584.9 (2) Å3	0.35 × 0.25 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	5924 independent reflections
Radiation source: fine-focus sealed tube	5288 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.633, Tmax = 0.813	k = −43→42
24727 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0423P)2 + 3.5411P] where P = (Fo2 + 2Fc2)/3
5924 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.38 e Å−3
2 restraints	Δρmin = −1.15 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.77625 (3)	0.625981 (7)	0.62161 (2)	0.03525 (9)
Cl1	0.79773 (15)	0.56055 (3)	0.53317 (11)	0.0513 (2)
Cl2	0.86453 (17)	0.60335 (4)	0.86654 (11)	0.0633 (3)
Cl3	1.06377 (14)	0.64544 (4)	0.66027 (14)	0.0661 (3)
Cl4	0.47849 (13)	0.61972 (3)	0.58488 (12)	0.0492 (2)
O1	0.6997 (4)	0.64512 (8)	0.4078 (3)	0.0419 (6)
O2	0.6522 (5)	0.69652 (10)	0.2599 (3)	0.0665 (9)
O3	0.1333 (4)	0.58105 (10)	0.2844 (4)	0.0573 (8)
O4	0.2708 (4)	0.62339 (9)	0.1913 (4)	0.0566 (8)
O5	0.5646 (4)	0.63000 (9)	0.0768 (3)	0.0476 (6)
N1	0.7356 (4)	0.69426 (9)	0.6318 (3)	0.0388 (7)
N3	0.4799 (4)	0.56215 (9)	0.1803 (3)	0.0376 (6)
C1	0.6875 (5)	0.68256 (12)	0.3810 (4)	0.0439 (9)
C2	0.7133 (5)	0.71104 (11)	0.5058 (4)	0.0408 (8)
C3	0.7086 (7)	0.75223 (13)	0.4836 (5)	0.0591 (12)
H3A	0.6919	0.7626	0.3930	0.071*
C4	0.7287 (7)	0.77719 (13)	0.5963 (5)	0.0638 (13)
H4	0.7297	0.8049	0.5840	0.077*
C5	0.7481 (6)	0.76113 (12)	0.7317 (5)	0.0505 (10)
C6	0.7654 (7)	0.78527 (14)	0.8525 (6)	0.0676 (14)
H6	0.7710	0.8131	0.8455	0.081*
C7	0.7741 (8)	0.76872 (16)	0.9772 (6)	0.0747 (16)
H7	0.7831	0.7851	1.0550	0.090*
C8	0.7696 (8)	0.72689 (16)	0.9909 (5)	0.0726 (15)
H8	0.7743	0.7157	1.0774	0.087*
C9	0.7581 (7)	0.70231 (14)	0.8775 (5)	0.0573 (12)
H9	0.7571	0.6746	0.8882	0.069*
C10	0.7480 (5)	0.71862 (11)	0.7467 (4)	0.0421 (8)
C11	0.2513 (5)	0.59121 (12)	0.2346 (4)	0.0423 (8)
C12	0.3641 (5)	0.55578 (11)	0.2379 (4)	0.0412 (8)
C13	0.3513 (6)	0.51870 (13)	0.2949 (5)	0.0530 (10)
H13	0.2686	0.5143	0.3337	0.064*
C14	0.4601 (7)	0.48872 (13)	0.2940 (5)	0.0599 (12)
H14	0.4528	0.4639	0.3339	0.072*
C15	0.5835 (6)	0.49474 (12)	0.2337 (4)	0.0503 (10)
C16	0.7009 (7)	0.46501 (15)	0.2295 (6)	0.0681 (14)
H16	0.7010	0.4399	0.2703	0.082*
C17	0.8142 (7)	0.47287 (17)	0.1659 (6)	0.0739 (16)
H17	0.8914	0.4531	0.1638	0.089*
C18	0.8150 (6)	0.51091 (17)	0.1030 (6)	0.0671 (14)
H18	0.8917	0.5156	0.0584	0.081*
C19	0.7058 (5)	0.54069 (14)	0.1064 (5)	0.0524 (10)
H19	0.7081	0.5656	0.0655	0.063*
C20	0.5903 (5)	0.53305 (11)	0.1727 (4)	0.0418 (8)
C21	0.0198 (7)	0.61294 (16)	0.2925 (7)	0.0707 (14)
H21A	−0.0661	0.6020	0.3231	0.106*
H21B	−0.0355	0.6251	0.1989	0.106*
H21C	0.0859	0.6328	0.3609	0.106*
C22	0.4323 (7)	0.64239 (17)	−0.0535 (5)	0.0680 (13)
H22A	0.3222	0.6360	−0.0511	0.102*
H22B	0.4445	0.6288	−0.1334	0.102*
H22C	0.4400	0.6709	−0.0649	0.102*
H3	0.490 (6)	0.5852 (7)	0.145 (4)	0.051 (13)*
H5	0.589 (7)	0.6495 (10)	0.135 (4)	0.069 (16)*

	U11	U22	U33	U12	U13	U23
Sn1	0.03944 (14)	0.03703 (14)	0.02901 (13)	0.00101 (10)	0.01300 (10)	0.00026 (9)
Cl1	0.0677 (7)	0.0394 (5)	0.0486 (5)	0.0063 (4)	0.0244 (5)	−0.0038 (4)
Cl2	0.0838 (8)	0.0711 (7)	0.0352 (5)	0.0275 (6)	0.0232 (5)	0.0130 (5)
Cl3	0.0402 (6)	0.0898 (9)	0.0675 (7)	−0.0076 (5)	0.0202 (5)	−0.0077 (6)
Cl4	0.0413 (5)	0.0480 (5)	0.0587 (6)	−0.0016 (4)	0.0200 (4)	0.0033 (4)
O1	0.0560 (16)	0.0409 (14)	0.0290 (12)	−0.0004 (12)	0.0168 (11)	−0.0010 (10)
O2	0.113 (3)	0.0531 (18)	0.0342 (15)	−0.0056 (18)	0.0291 (17)	0.0064 (13)
O3	0.0554 (18)	0.0594 (19)	0.071 (2)	−0.0112 (14)	0.0394 (16)	−0.0129 (15)
O4	0.067 (2)	0.0469 (17)	0.067 (2)	0.0100 (14)	0.0382 (17)	0.0064 (14)
O5	0.0541 (17)	0.0469 (16)	0.0389 (14)	−0.0048 (13)	0.0151 (13)	−0.0037 (12)
N1	0.0468 (17)	0.0349 (16)	0.0379 (16)	−0.0054 (13)	0.0199 (14)	−0.0032 (12)
N3	0.0431 (17)	0.0348 (16)	0.0344 (15)	−0.0011 (13)	0.0147 (13)	−0.0012 (12)
C1	0.054 (2)	0.046 (2)	0.0339 (18)	−0.0029 (17)	0.0194 (17)	0.0027 (15)
C2	0.050 (2)	0.0383 (19)	0.0363 (18)	−0.0022 (16)	0.0187 (16)	0.0012 (15)
C3	0.089 (4)	0.043 (2)	0.050 (2)	−0.006 (2)	0.032 (2)	0.0099 (19)
C4	0.096 (4)	0.034 (2)	0.067 (3)	−0.006 (2)	0.039 (3)	−0.002 (2)
C5	0.064 (3)	0.036 (2)	0.058 (2)	−0.0072 (18)	0.031 (2)	−0.0069 (18)
C6	0.096 (4)	0.041 (2)	0.078 (3)	−0.011 (2)	0.046 (3)	−0.021 (2)
C7	0.111 (5)	0.063 (3)	0.070 (3)	−0.015 (3)	0.057 (3)	−0.030 (3)
C8	0.114 (5)	0.069 (3)	0.055 (3)	−0.018 (3)	0.055 (3)	−0.016 (2)
C9	0.089 (3)	0.045 (2)	0.051 (2)	−0.012 (2)	0.042 (2)	−0.0110 (19)
C10	0.052 (2)	0.0368 (19)	0.043 (2)	−0.0080 (16)	0.0240 (18)	−0.0077 (15)
C11	0.043 (2)	0.046 (2)	0.0396 (19)	−0.0044 (16)	0.0181 (17)	−0.0102 (16)
C12	0.045 (2)	0.040 (2)	0.0386 (19)	−0.0048 (16)	0.0167 (16)	−0.0045 (15)
C13	0.064 (3)	0.044 (2)	0.056 (2)	−0.010 (2)	0.028 (2)	0.0029 (19)
C14	0.083 (3)	0.036 (2)	0.058 (3)	−0.007 (2)	0.024 (2)	0.0033 (19)
C15	0.059 (3)	0.037 (2)	0.043 (2)	0.0062 (18)	0.0070 (19)	−0.0042 (16)
C16	0.078 (3)	0.045 (3)	0.064 (3)	0.018 (2)	0.009 (3)	−0.006 (2)
C17	0.062 (3)	0.070 (3)	0.073 (3)	0.028 (3)	0.008 (3)	−0.017 (3)
C18	0.046 (3)	0.083 (4)	0.068 (3)	0.009 (2)	0.018 (2)	−0.024 (3)
C19	0.045 (2)	0.058 (3)	0.054 (2)	0.0022 (19)	0.0180 (19)	−0.011 (2)
C20	0.042 (2)	0.0378 (19)	0.0391 (19)	0.0025 (15)	0.0087 (16)	−0.0082 (15)
C21	0.061 (3)	0.075 (3)	0.093 (4)	−0.003 (2)	0.048 (3)	−0.024 (3)
C22	0.086 (4)	0.077 (3)	0.043 (2)	0.001 (3)	0.027 (2)	0.001 (2)

Sn1—O1	2.083 (2)	C7—C8	1.400 (7)
Sn1—N1	2.305 (3)	C7—H7	0.9300
Sn1—Cl1	2.3838 (10)	C8—C9	1.373 (6)
Sn1—Cl3	2.3853 (11)	C8—H8	0.9300
Sn1—Cl2	2.3937 (10)	C9—C10	1.391 (6)
Sn1—Cl4	2.3947 (10)	C9—H9	0.9300
O1—C1	1.270 (5)	C11—C12	1.505 (5)
O2—C1	1.223 (4)	C12—C13	1.382 (6)
O3—C11	1.317 (5)	C13—C14	1.356 (7)
O3—C21	1.451 (6)	C13—H13	0.9300
O4—C11	1.190 (5)	C14—C15	1.404 (7)
O5—C22	1.409 (6)	C14—H14	0.9300
O5—H5	0.842 (10)	C15—C16	1.410 (6)
N1—C2	1.325 (5)	C15—C20	1.425 (6)
N1—C10	1.379 (5)	C16—C17	1.362 (8)
N3—C12	1.328 (5)	C16—H16	0.9300
N3—C20	1.364 (5)	C17—C18	1.415 (8)
N3—H3	0.860 (10)	C17—H17	0.9300
C1—C2	1.517 (5)	C18—C19	1.360 (6)
C2—C3	1.387 (6)	C18—H18	0.9300
C3—C4	1.358 (6)	C19—C20	1.397 (6)
C3—H3A	0.9300	C19—H19	0.9300
C4—C5	1.408 (6)	C21—H21A	0.9600
C4—H4	0.9300	C21—H21B	0.9600
C5—C6	1.413 (6)	C21—H21C	0.9600
C5—C10	1.423 (5)	C22—H22A	0.9600
C6—C7	1.342 (7)	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
O1—Sn1—N1	75.66 (10)	C8—C9—C10	120.5 (4)
O1—Sn1—Cl1	86.24 (8)	C8—C9—H9	119.8
N1—Sn1—Cl1	161.86 (8)	C10—C9—H9	119.8
O1—Sn1—Cl3	88.44 (8)	N1—C10—C9	121.0 (3)
N1—Sn1—Cl3	83.31 (9)	N1—C10—C5	119.9 (3)
Cl1—Sn1—Cl3	95.15 (4)	C9—C10—C5	119.0 (4)
O1—Sn1—Cl2	179.45 (8)	O4—C11—O3	126.9 (4)
N1—Sn1—Cl2	104.89 (8)	O4—C11—C12	122.5 (4)
Cl1—Sn1—Cl2	93.21 (4)	O3—C11—C12	110.6 (3)
Cl3—Sn1—Cl2	91.59 (5)	N3—C12—C13	120.7 (4)
O1—Sn1—Cl4	88.95 (8)	N3—C12—C11	115.3 (3)
N1—Sn1—Cl4	85.89 (8)	C13—C12—C11	123.9 (4)
Cl1—Sn1—Cl4	95.12 (4)	C14—C13—C12	119.5 (4)
Cl3—Sn1—Cl4	169.21 (4)	C14—C13—H13	120.2
Cl2—Sn1—Cl4	91.12 (4)	C12—C13—H13	120.2
C1—O1—Sn1	119.0 (2)	C13—C14—C15	120.8 (4)
C11—O3—C21	116.3 (4)	C13—C14—H14	119.6
C22—O5—H5	108 (4)	C15—C14—H14	119.6
C2—N1—C10	119.0 (3)	C16—C15—C14	123.8 (5)
C2—N1—Sn1	110.0 (2)	C16—C15—C20	118.0 (5)
C10—N1—Sn1	130.7 (2)	C14—C15—C20	118.2 (4)
C12—N3—C20	122.7 (3)	C17—C16—C15	120.3 (5)
C12—N3—H3	122 (3)	C17—C16—H16	119.8
C20—N3—H3	116 (3)	C15—C16—H16	119.8
O2—C1—O1	123.4 (4)	C16—C17—C18	120.4 (4)
O2—C1—C2	118.9 (4)	C16—C17—H17	119.8
O1—C1—C2	117.6 (3)	C18—C17—H17	119.8
N1—C2—C3	123.6 (4)	C19—C18—C17	121.3 (5)
N1—C2—C1	116.4 (3)	C19—C18—H18	119.3
C3—C2—C1	120.0 (3)	C17—C18—H18	119.3
C4—C3—C2	119.0 (4)	C18—C19—C20	118.7 (5)
C4—C3—H3A	120.5	C18—C19—H19	120.6
C2—C3—H3A	120.5	C20—C19—H19	120.6
C3—C4—C5	120.0 (4)	N3—C20—C19	120.8 (4)
C3—C4—H4	120.0	N3—C20—C15	118.0 (4)
C5—C4—H4	120.0	C19—C20—C15	121.2 (4)
C4—C5—C6	123.1 (4)	O3—C21—H21A	109.5
C4—C5—C10	118.3 (4)	O3—C21—H21B	109.5
C6—C5—C10	118.6 (4)	H21A—C21—H21B	109.5
C7—C6—C5	121.0 (4)	O3—C21—H21C	109.5
C7—C6—H6	119.5	H21A—C21—H21C	109.5
C5—C6—H6	119.5	H21B—C21—H21C	109.5
C6—C7—C8	120.3 (4)	O5—C22—H22A	109.5
C6—C7—H7	119.8	O5—C22—H22B	109.5
C8—C7—H7	119.8	H22A—C22—H22B	109.5
C9—C8—C7	120.5 (5)	O5—C22—H22C	109.5
C9—C8—H8	119.8	H22A—C22—H22C	109.5
C7—C8—H8	119.8	H22B—C22—H22C	109.5
N1—Sn1—O1—C1	8.4 (3)	Sn1—N1—C10—C9	−12.5 (6)
Cl1—Sn1—O1—C1	−170.3 (3)	C2—N1—C10—C5	−4.1 (6)
Cl3—Sn1—O1—C1	−75.1 (3)	Sn1—N1—C10—C5	168.4 (3)
Cl2—Sn1—O1—C1	−169 (9)	C8—C9—C10—N1	−179.7 (5)
Cl4—Sn1—O1—C1	94.5 (3)	C8—C9—C10—C5	−0.6 (7)
O1—Sn1—N1—C2	−10.0 (3)	C4—C5—C10—N1	2.4 (7)
Cl1—Sn1—N1—C2	−6.0 (5)	C6—C5—C10—N1	−178.4 (4)
Cl3—Sn1—N1—C2	80.1 (3)	C4—C5—C10—C9	−176.7 (5)
Cl2—Sn1—N1—C2	170.0 (2)	C6—C5—C10—C9	2.5 (7)
Cl4—Sn1—N1—C2	−100.0 (3)	C21—O3—C11—O4	−2.7 (6)
O1—Sn1—N1—C10	177.0 (3)	C21—O3—C11—C12	177.7 (4)
Cl1—Sn1—N1—C10	−179.0 (2)	C20—N3—C12—C13	0.6 (6)
Cl3—Sn1—N1—C10	−92.9 (3)	C20—N3—C12—C11	−179.0 (3)
Cl2—Sn1—N1—C10	−3.0 (3)	O4—C11—C12—N3	−4.2 (6)
Cl4—Sn1—N1—C10	87.0 (3)	O3—C11—C12—N3	175.5 (3)
Sn1—O1—C1—O2	176.1 (3)	O4—C11—C12—C13	176.2 (4)
Sn1—O1—C1—C2	−5.7 (5)	O3—C11—C12—C13	−4.1 (5)
C10—N1—C2—C3	2.8 (6)	N3—C12—C13—C14	1.0 (6)
Sn1—N1—C2—C3	−171.2 (4)	C11—C12—C13—C14	−179.4 (4)
C10—N1—C2—C1	−175.6 (3)	C12—C13—C14—C15	−1.1 (7)
Sn1—N1—C2—C1	10.4 (4)	C13—C14—C15—C16	179.8 (5)
O2—C1—C2—N1	174.0 (4)	C13—C14—C15—C20	−0.5 (7)
O1—C1—C2—N1	−4.2 (6)	C14—C15—C16—C17	178.4 (5)
O2—C1—C2—C3	−4.5 (6)	C20—C15—C16—C17	−1.3 (7)
O1—C1—C2—C3	177.3 (4)	C15—C16—C17—C18	−0.2 (8)
N1—C2—C3—C4	0.4 (8)	C16—C17—C18—C19	1.2 (8)
C1—C2—C3—C4	178.8 (4)	C17—C18—C19—C20	−0.5 (7)
C2—C3—C4—C5	−2.1 (8)	C12—N3—C20—C19	177.7 (4)
C3—C4—C5—C6	−178.5 (5)	C12—N3—C20—C15	−2.1 (5)
C3—C4—C5—C10	0.8 (8)	C18—C19—C20—N3	179.2 (4)
C4—C5—C6—C7	176.3 (6)	C18—C19—C20—C15	−1.1 (6)
C10—C5—C6—C7	−2.9 (8)	C16—C15—C20—N3	−178.3 (4)
C5—C6—C7—C8	1.3 (9)	C14—C15—C20—N3	2.0 (6)
C6—C7—C8—C9	0.7 (10)	C16—C15—C20—C19	2.0 (6)
C7—C8—C9—C10	−1.0 (9)	C14—C15—C20—C19	−177.8 (4)
C2—N1—C10—C9	175.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2	0.84 (1)	1.95 (1)	2.785 (4)	176 (5)
N3—H3···O5	0.86 (1)	1.85 (2)	2.693 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2	0.84 (1)	1.95 (1)	2.785 (4)	176 (5)
N3—H3⋯O5	0.86 (1)	1.85 (2)	2.693 (4)	166 (4)