2-[(Propan-2-yl-oxy)carbon-yl]quinolin-1-ium tetra-chlorido(quinoline-2-carboxyl-ato-κ(2)N,O)stannate(IV).

In the title salt, (C(13)H(14)NO(2))[Sn(C(10)H(6)NO(2))Cl(4)], the Sn(IV) cation is N,O-chelated by the quinolincarboxyl-ate unit and further coordinated by four Cl(-) anions in a distorted octa-hedral geometry. In the crystal, the 2-[(propan-2-yl-oxy)-carbon-yl]quinolin-1-ium cation is linked to the Sn complex anion by an N-H⋯O hydrogen bond.

Related literature

For related stannates, see: Vafaee et al. (2010 ▶); Najafi et al. (2012 ▶).

Experimental

Crystal data

(C13H14NO2)[Sn(C10H6NO2)Cl4]

M = 648.90

Monoclinic,

a = 7.1932 (2) Å

b = 17.8616 (4) Å

c = 19.1963 (5) Å

β = 95.156 (3)°

V = 2456.40 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.51 mm−1

T = 100 K

0.40 × 0.40 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.584, T max = 0.752

16873 measured reflections

5665 independent reflections

4896 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.062

S = 1.00

5665 reflections

311 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.59 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/S1600536812019496/xu5530sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019496/xu5530Isup2.hkl

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

(C13H14NO2)[Sn(C10H6NO2)Cl4]	F(000) = 1288
Mr = 648.90	Dx = 1.755 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8443 reflections
a = 7.1932 (2) Å	θ = 2.3–27.5°
b = 17.8616 (4) Å	µ = 1.51 mm−1
c = 19.1963 (5) Å	T = 100 K
β = 95.156 (3)°	Prism, light yellow
V = 2456.40 (11) Å3	0.40 × 0.40 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	5665 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4896 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −23→22
Tmin = 0.584, Tmax = 0.752	l = −24→14
16873 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0278P)2 + 0.7987P] where P = (Fo2 + 2Fc2)/3
5665 reflections	(Δ/σ)max = 0.002
311 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.59 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
Sn1	0.53403 (2)	0.617340 (8)	0.681802 (8)	0.01204 (5)
Cl1	0.74011 (8)	0.54275 (3)	0.75709 (3)	0.01880 (13)
Cl2	0.55407 (8)	0.54164 (3)	0.58147 (3)	0.01864 (13)
Cl3	0.26300 (8)	0.55748 (3)	0.71743 (3)	0.01923 (13)
Cl4	0.78982 (8)	0.69944 (3)	0.66038 (3)	0.01852 (13)
O1	0.3671 (2)	0.68976 (8)	0.61805 (9)	0.0160 (3)
O2	0.2388 (2)	0.80248 (9)	0.60590 (9)	0.0214 (4)
O3	0.1647 (2)	0.96046 (9)	0.38812 (9)	0.0212 (4)
O4	0.1828 (3)	0.92896 (9)	0.50283 (10)	0.0288 (4)
N1	0.4572 (2)	0.71449 (10)	0.75561 (10)	0.0123 (4)
N2	0.0861 (3)	0.78646 (10)	0.46623 (11)	0.0137 (4)
H2	0.128 (4)	0.7973 (15)	0.5093 (7)	0.033 (8)*
C1	0.3248 (3)	0.75441 (12)	0.64113 (13)	0.0152 (5)
C2	0.3810 (3)	0.77079 (12)	0.71758 (12)	0.0137 (5)
C3	0.3490 (3)	0.84213 (12)	0.74524 (13)	0.0175 (5)
H3	0.2964	0.8810	0.7160	0.021*
C4	0.3946 (3)	0.85458 (13)	0.81454 (13)	0.0169 (5)
H4	0.3792	0.9030	0.8336	0.020*
C5	0.4647 (3)	0.79574 (12)	0.85798 (13)	0.0139 (5)
C6	0.5036 (3)	0.80425 (13)	0.93158 (13)	0.0179 (5)
H6	0.4848	0.8514	0.9528	0.021*
C7	0.5676 (3)	0.74510 (14)	0.97183 (13)	0.0195 (5)
H7	0.5947	0.7513	1.0208	0.023*
C8	0.5937 (3)	0.67457 (14)	0.94067 (13)	0.0178 (5)
H8	0.6365	0.6336	0.9693	0.021*
C9	0.5583 (3)	0.66412 (13)	0.86986 (13)	0.0153 (5)
H9	0.5762	0.6163	0.8499	0.018*
C10	0.4955 (3)	0.72447 (12)	0.82692 (12)	0.0121 (5)
C11	0.1536 (3)	0.91484 (13)	0.44172 (13)	0.0153 (5)
C12	0.0940 (3)	0.83797 (12)	0.41617 (13)	0.0137 (5)
C13	0.0433 (3)	0.82038 (13)	0.34648 (13)	0.0151 (5)
H13	0.0506	0.8570	0.3110	0.018*
C14	−0.0177 (3)	0.74902 (13)	0.32982 (13)	0.0168 (5)
H14	−0.0518	0.7363	0.2823	0.020*
C15	−0.0301 (3)	0.69484 (12)	0.38213 (13)	0.0148 (5)
C16	−0.0970 (3)	0.62128 (12)	0.36872 (14)	0.0184 (5)
H16	−0.1302	0.6056	0.3220	0.022*
C17	−0.1139 (3)	0.57292 (13)	0.42255 (14)	0.0196 (5)
H17	−0.1621	0.5241	0.4132	0.023*
C18	−0.0606 (3)	0.59455 (13)	0.49189 (14)	0.0178 (5)
H18	−0.0744	0.5600	0.5287	0.021*
C19	0.0103 (3)	0.66398 (12)	0.50750 (13)	0.0160 (5)
H19	0.0496	0.6774	0.5544	0.019*
C20	0.0238 (3)	0.71517 (12)	0.45259 (12)	0.0131 (5)
C21	0.2217 (3)	1.03864 (12)	0.40355 (14)	0.0209 (5)
H21A	0.1958	1.0519	0.4524	0.025*
C22	0.4265 (4)	1.04469 (15)	0.39607 (17)	0.0311 (7)
H22A	0.4679	1.0962	0.4061	0.047*
H22B	0.4509	1.0315	0.3482	0.047*
H22C	0.4948	1.0104	0.4290	0.047*
C23	0.1016 (4)	1.08525 (15)	0.35205 (17)	0.0370 (7)
H23A	0.1312	1.1383	0.3597	0.056*
H23B	−0.0302	1.0766	0.3586	0.056*
H23C	0.1257	1.0712	0.3043	0.056*

	U11	U22	U33	U12	U13	U23
Sn1	0.01605 (9)	0.01020 (8)	0.00981 (9)	−0.00155 (6)	0.00086 (6)	−0.00091 (6)
Cl1	0.0217 (3)	0.0154 (3)	0.0188 (3)	0.0028 (2)	−0.0009 (2)	0.0007 (2)
Cl2	0.0258 (3)	0.0169 (3)	0.0137 (3)	−0.0036 (2)	0.0044 (2)	−0.0055 (2)
Cl3	0.0201 (3)	0.0194 (3)	0.0188 (3)	−0.0065 (2)	0.0051 (2)	−0.0038 (2)
Cl4	0.0215 (3)	0.0189 (3)	0.0155 (3)	−0.0071 (2)	0.0042 (2)	−0.0020 (2)
O1	0.0231 (8)	0.0126 (8)	0.0116 (9)	0.0012 (7)	−0.0017 (7)	−0.0017 (6)
O2	0.0326 (9)	0.0148 (8)	0.0154 (10)	0.0037 (7)	−0.0051 (8)	0.0016 (7)
O3	0.0337 (10)	0.0132 (8)	0.0170 (10)	−0.0065 (7)	0.0033 (8)	0.0011 (7)
O4	0.0488 (12)	0.0205 (9)	0.0158 (10)	−0.0068 (8)	−0.0051 (9)	0.0022 (7)
N1	0.0138 (9)	0.0121 (9)	0.0113 (10)	−0.0019 (8)	0.0025 (8)	−0.0006 (7)
N2	0.0129 (9)	0.0162 (10)	0.0115 (11)	0.0008 (8)	−0.0014 (8)	0.0007 (8)
C1	0.0179 (11)	0.0149 (11)	0.0129 (12)	−0.0040 (9)	0.0026 (9)	0.0009 (9)
C2	0.0163 (11)	0.0125 (11)	0.0123 (12)	−0.0040 (9)	0.0009 (9)	−0.0003 (9)
C3	0.0224 (12)	0.0117 (11)	0.0180 (14)	0.0006 (10)	−0.0005 (10)	0.0004 (9)
C4	0.0174 (11)	0.0123 (11)	0.0208 (14)	−0.0019 (10)	0.0004 (10)	−0.0036 (10)
C5	0.0102 (10)	0.0169 (11)	0.0148 (13)	−0.0028 (9)	0.0015 (9)	−0.0037 (9)
C6	0.0166 (11)	0.0219 (12)	0.0153 (13)	−0.0044 (10)	0.0023 (10)	−0.0080 (10)
C7	0.0163 (11)	0.0322 (14)	0.0102 (13)	−0.0028 (10)	0.0012 (9)	−0.0015 (10)
C8	0.0167 (11)	0.0258 (13)	0.0110 (13)	0.0016 (10)	0.0018 (9)	0.0043 (10)
C9	0.0151 (11)	0.0157 (11)	0.0150 (13)	−0.0001 (9)	0.0020 (9)	−0.0001 (9)
C10	0.0114 (10)	0.0132 (10)	0.0117 (12)	−0.0021 (9)	0.0008 (9)	0.0002 (9)
C11	0.0142 (11)	0.0161 (11)	0.0153 (13)	0.0034 (9)	0.0002 (9)	0.0008 (9)
C12	0.0101 (10)	0.0144 (11)	0.0165 (13)	0.0011 (9)	0.0000 (9)	0.0014 (9)
C13	0.0135 (11)	0.0175 (11)	0.0145 (13)	0.0005 (9)	0.0024 (9)	0.0036 (9)
C14	0.0160 (11)	0.0210 (12)	0.0131 (13)	0.0017 (10)	0.0000 (10)	−0.0002 (10)
C15	0.0089 (10)	0.0175 (11)	0.0179 (13)	0.0033 (9)	0.0005 (9)	0.0001 (9)
C16	0.0154 (11)	0.0185 (12)	0.0206 (14)	0.0001 (9)	−0.0025 (10)	−0.0035 (10)
C17	0.0166 (11)	0.0142 (11)	0.0275 (15)	−0.0013 (10)	−0.0007 (10)	−0.0017 (10)
C18	0.0156 (11)	0.0165 (11)	0.0213 (14)	0.0006 (9)	0.0021 (10)	0.0039 (10)
C19	0.0142 (11)	0.0186 (12)	0.0148 (13)	0.0003 (9)	−0.0008 (9)	0.0023 (9)
C20	0.0092 (10)	0.0152 (11)	0.0148 (13)	0.0003 (9)	0.0011 (9)	−0.0009 (9)
C21	0.0289 (13)	0.0123 (11)	0.0221 (15)	−0.0049 (10)	0.0050 (11)	−0.0027 (10)
C22	0.0281 (14)	0.0243 (14)	0.0417 (19)	−0.0089 (12)	0.0078 (13)	−0.0093 (13)
C23	0.0507 (18)	0.0193 (13)	0.039 (2)	0.0085 (13)	−0.0061 (15)	−0.0010 (12)

Sn1—O1	2.0851 (15)	C8—H8	0.9500
Sn1—N1	2.3377 (19)	C9—C10	1.407 (3)
Sn1—Cl2	2.3683 (6)	C9—H9	0.9500
Sn1—Cl3	2.3773 (6)	C11—C12	1.507 (3)
Sn1—Cl1	2.3824 (6)	C12—C13	1.391 (3)
Sn1—Cl4	2.4168 (6)	C13—C14	1.376 (3)
O1—C1	1.283 (3)	C13—H13	0.9500
O2—C1	1.225 (3)	C14—C15	1.403 (3)
O3—C11	1.321 (3)	C14—H14	0.9500
O3—C21	1.478 (3)	C15—C20	1.420 (3)
O4—C11	1.200 (3)	C15—C16	1.415 (3)
N1—C2	1.332 (3)	C16—C17	1.361 (4)
N1—C10	1.383 (3)	C16—H16	0.9500
N2—C12	1.335 (3)	C17—C18	1.406 (3)
N2—C20	1.367 (3)	C17—H17	0.9500
N2—H2	0.876 (10)	C18—C19	1.364 (3)
C1—C2	1.515 (3)	C18—H18	0.9500
C2—C3	1.407 (3)	C19—C20	1.405 (3)
C3—C4	1.360 (3)	C19—H19	0.9500
C3—H3	0.9500	C21—C22	1.497 (3)
C4—C5	1.407 (3)	C21—C23	1.504 (4)
C4—H4	0.9500	C21—H21A	1.0000
C5—C6	1.423 (3)	C22—H22A	0.9800
C5—C10	1.431 (3)	C22—H22B	0.9800
C6—C7	1.364 (3)	C22—H22C	0.9800
C6—H6	0.9500	C23—H23A	0.9800
C7—C8	1.414 (3)	C23—H23B	0.9800
C7—H7	0.9500	C23—H23C	0.9800
C8—C9	1.373 (3)
O1—Sn1—N1	74.94 (6)	N1—C10—C5	120.2 (2)
O1—Sn1—Cl2	87.18 (5)	C9—C10—C5	119.4 (2)
N1—Sn1—Cl2	162.12 (5)	O4—C11—O3	127.9 (2)
O1—Sn1—Cl3	90.24 (5)	O4—C11—C12	122.0 (2)
N1—Sn1—Cl3	85.12 (5)	O3—C11—C12	110.1 (2)
Cl2—Sn1—Cl3	95.08 (2)	N2—C12—C13	120.8 (2)
O1—Sn1—Cl1	175.51 (4)	N2—C12—C11	115.0 (2)
N1—Sn1—Cl1	102.45 (5)	C13—C12—C11	124.1 (2)
Cl2—Sn1—Cl1	95.39 (2)	C14—C13—C12	118.9 (2)
Cl3—Sn1—Cl1	93.19 (2)	C14—C13—H13	120.5
O1—Sn1—Cl4	86.02 (5)	C12—C13—H13	120.5
N1—Sn1—Cl4	82.98 (5)	C13—C14—C15	120.8 (2)
Cl2—Sn1—Cl4	96.04 (2)	C13—C14—H14	119.6
Cl3—Sn1—Cl4	168.08 (2)	C15—C14—H14	119.6
Cl1—Sn1—Cl4	90.05 (2)	C14—C15—C20	118.4 (2)
C1—O1—Sn1	119.85 (15)	C14—C15—C16	123.6 (2)
C11—O3—C21	117.52 (19)	C20—C15—C16	118.0 (2)
C2—N1—C10	118.74 (19)	C17—C16—C15	120.2 (2)
C2—N1—Sn1	109.66 (15)	C17—C16—H16	119.9
C10—N1—Sn1	131.19 (14)	C15—C16—H16	119.9
C12—N2—C20	122.6 (2)	C16—C17—C18	120.6 (2)
C12—N2—H2	119.5 (19)	C16—C17—H17	119.7
C20—N2—H2	117.9 (19)	C18—C17—H17	119.7
O2—C1—O1	124.3 (2)	C19—C18—C17	121.5 (2)
O2—C1—C2	118.5 (2)	C19—C18—H18	119.2
O1—C1—C2	117.20 (19)	C17—C18—H18	119.2
N1—C2—C3	123.4 (2)	C18—C19—C20	118.5 (2)
N1—C2—C1	116.50 (19)	C18—C19—H19	120.8
C3—C2—C1	120.1 (2)	C20—C19—H19	120.8
C4—C3—C2	118.9 (2)	N2—C20—C19	120.4 (2)
C4—C3—H3	120.5	N2—C20—C15	118.5 (2)
C2—C3—H3	120.5	C19—C20—C15	121.1 (2)
C3—C4—C5	120.0 (2)	O3—C21—C22	107.85 (19)
C3—C4—H4	120.0	O3—C21—C23	105.0 (2)
C5—C4—H4	120.0	C22—C21—C23	114.1 (2)
C4—C5—C6	122.4 (2)	O3—C21—H21A	109.9
C4—C5—C10	118.6 (2)	C22—C21—H21A	109.9
C6—C5—C10	119.0 (2)	C23—C21—H21A	109.9
C7—C6—C5	120.4 (2)	C21—C22—H22A	109.5
C7—C6—H6	119.8	C21—C22—H22B	109.5
C5—C6—H6	119.8	H22A—C22—H22B	109.5
C6—C7—C8	120.1 (2)	C21—C22—H22C	109.5
C6—C7—H7	120.0	H22A—C22—H22C	109.5
C8—C7—H7	120.0	H22B—C22—H22C	109.5
C9—C8—C7	121.3 (2)	C21—C23—H23A	109.5
C9—C8—H8	119.3	C21—C23—H23B	109.5
C7—C8—H8	119.3	H23A—C23—H23B	109.5
C8—C9—C10	119.8 (2)	C21—C23—H23C	109.5
C8—C9—H9	120.1	H23A—C23—H23C	109.5
C10—C9—H9	120.1	H23B—C23—H23C	109.5
N1—C10—C9	120.4 (2)
N1—Sn1—O1—C1	10.22 (16)	C2—N1—C10—C5	−4.1 (3)
Cl2—Sn1—O1—C1	−169.82 (16)	Sn1—N1—C10—C5	167.66 (15)
Cl3—Sn1—O1—C1	95.10 (16)	C8—C9—C10—N1	−179.2 (2)
Cl4—Sn1—O1—C1	−73.57 (16)	C8—C9—C10—C5	−1.6 (3)
O1—Sn1—N1—C2	−11.88 (14)	C4—C5—C10—N1	0.2 (3)
Cl2—Sn1—N1—C2	−12.0 (3)	C6—C5—C10—N1	179.38 (19)
Cl3—Sn1—N1—C2	−103.44 (14)	C4—C5—C10—C9	−177.4 (2)
Cl1—Sn1—N1—C2	164.36 (13)	C6—C5—C10—C9	1.7 (3)
Cl4—Sn1—N1—C2	75.87 (14)	C21—O3—C11—O4	0.7 (4)
O1—Sn1—N1—C10	175.81 (19)	C21—O3—C11—C12	−179.99 (18)
Cl2—Sn1—N1—C10	175.67 (13)	C20—N2—C12—C13	−1.9 (3)
Cl3—Sn1—N1—C10	84.25 (18)	C20—N2—C12—C11	175.94 (19)
Cl1—Sn1—N1—C10	−7.94 (19)	O4—C11—C12—N2	−3.4 (3)
Cl4—Sn1—N1—C10	−96.43 (18)	O3—C11—C12—N2	177.26 (19)
Sn1—O1—C1—O2	174.66 (17)	O4—C11—C12—C13	174.3 (2)
Sn1—O1—C1—C2	−7.1 (3)	O3—C11—C12—C13	−5.0 (3)
C10—N1—C2—C3	4.6 (3)	N2—C12—C13—C14	0.8 (3)
Sn1—N1—C2—C3	−168.75 (18)	C11—C12—C13—C14	−176.8 (2)
C10—N1—C2—C1	−174.27 (19)	C12—C13—C14—C15	0.5 (3)
Sn1—N1—C2—C1	12.3 (2)	C13—C14—C15—C20	−0.7 (3)
O2—C1—C2—N1	173.4 (2)	C13—C14—C15—C16	178.0 (2)
O1—C1—C2—N1	−4.9 (3)	C14—C15—C16—C17	−176.7 (2)
O2—C1—C2—C3	−5.5 (3)	C20—C15—C16—C17	2.1 (3)
O1—C1—C2—C3	176.1 (2)	C15—C16—C17—C18	−1.7 (4)
N1—C2—C3—C4	−1.2 (4)	C16—C17—C18—C19	−0.4 (4)
C1—C2—C3—C4	177.7 (2)	C17—C18—C19—C20	2.1 (3)
C2—C3—C4—C5	−2.8 (4)	C12—N2—C20—C19	−177.1 (2)
C3—C4—C5—C6	−175.9 (2)	C12—N2—C20—C15	1.6 (3)
C3—C4—C5—C10	3.2 (3)	C18—C19—C20—N2	177.0 (2)
C4—C5—C6—C7	178.6 (2)	C18—C19—C20—C15	−1.7 (3)
C10—C5—C6—C7	−0.6 (3)	C14—C15—C20—N2	−0.3 (3)
C5—C6—C7—C8	−0.8 (3)	C16—C15—C20—N2	−179.1 (2)
C6—C7—C8—C9	0.9 (4)	C14—C15—C20—C19	178.4 (2)
C7—C8—C9—C10	0.3 (3)	C16—C15—C20—C19	−0.4 (3)
C2—N1—C10—C9	173.6 (2)	C11—O3—C21—C22	97.2 (3)
Sn1—N1—C10—C9	−14.7 (3)	C11—O3—C21—C23	−140.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88 (1)	1.95 (1)	2.819 (3)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.88 (1)	1.95 (1)	2.819 (3)	169 (3)