2-[(Propan-2-yl­oxy)carbon­yl]quinolin-1-ium tetra­chlorido(quinoline-2-carboxyl­ato-κ2N,O)stannate(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536812019496

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m732

doi:10.1107/S1600536812019496

Open

access

2-[(Propan-2-yloxy)carbonyl]quinolin-1-ium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 30 April 2012; accepted 1 May 2012; online 5 May 2012)

In the title salt, (C₁₃H₁₄NO₂)[Sn(C₁₀H₆NO₂)Cl₄], the Sn^IV cation is N,O-chelated by the quinolincarboxylate unit and further coordinated by four Cl⁻ anions in a distorted octahedral geometry. In the crystal, the 2-[(propan-2-yloxy)carbonyl]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_r = 648.90
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.062
S = 1.00
5665 reflections
311 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.59 e Å⁻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)

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019496/xu5530sup1.cif

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

checkCIF report

Comment top

Stannic chloride and quinoline-2-carboxylic acid reacts in methanol medium to yield 2-(ethoxycarbonyl)quinolinium tetrachlorido(quinoline-2-carboxylatostannate(IV), which crystallizes a as a methanol solvate (Vafaee et al., 2010). The corresponding 2-(isoproproxycarbonyl)quinolinium salt (Scheme I) is obtained when isopropyl alcohol is used in placed of methanol; however, the compound does not has any solvent of crystallization. Tthe Sn^IV atom is chelated by the quinolincarboxylate unit and it exists in an octahedral coordination geometry (Fig. 1). The cation is linked to the anion by an N–H···O hydrogen bond (Table 1).

Related literature top

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

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol) and quinoline-2-carboxylic acid (0.17 g, 2 mmol) were loaded into a convection tube; the tube was filled with isopropyl alcohol and kept at 333 K. Light yellow crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (C₁₃H₁₄NO₂)[SnCl₄(C₁₀H₆NO₂)] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-[(Propan-2-yloxy)carbonyl]quinolin-1-ium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV) top

Crystal data top

(C₁₃H₁₄NO₂)[Sn(C₁₀H₆NO₂)Cl₄]	F(000) = 1288
M_r = 648.90	D_x = 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

Data collection top

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	R_int = 0.032
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scan	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −23→22
T_min = 0.584, T_max = 0.752	l = −24→14
16873 measured reflections

Refinement top

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(F_o²) + (0.0278P)² + 0.7987P] where P = (F_o² + 2F_c²)/3
5665 reflections	(Δ/σ)_max = 0.002
311 parameters	Δρ_max = 0.45 e Å⁻³
1 restraint	Δρ_min = −0.59 e Å⁻³

Crystal data top

(C₁₃H₁₄NO₂)[Sn(C₁₀H₆NO₂)Cl₄]	V = 2456.40 (11) Å³
M_r = 648.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1932 (2) Å	µ = 1.51 mm⁻¹
b = 17.8616 (4) Å	T = 100 K
c = 19.1963 (5) Å	0.40 × 0.40 × 0.20 mm
β = 95.156 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5665 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	4896 reflections with I > 2σ(I)
T_min = 0.584, T_max = 0.752	R_int = 0.032
16873 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.45 e Å⁻³
5665 reflections	Δρ_min = −0.59 e Å⁻³
311 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	(C₁₃H₁₄NO₂)[Sn(C₁₀H₆NO₂)Cl₄]
M_r	648.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.1932 (2), 17.8616 (4), 19.1963 (5)
β (°)	95.156 (3)
V (Å³)	2456.40 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.584, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	16873, 5665, 4896
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.062, 1.00
No. of reflections	5665
No. of parameters	311
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.59

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2012). Acta Cryst. E68, m738. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vafaee, M., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m390. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.