4-(Dimethyl­amino)­pyridinium tetra­chlorido(pyridine-2-carboxyl­ato-κ2N,O)stannate(IV)

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

doi:10.1107/S160053681201968X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m744

doi:10.1107/S160053681201968X

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4-(Dimethylamino)pyridinium tetrachlorido(pyridine-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 1 May 2012; accepted 2 May 2012; online 5 May 2012)

The reaction of 4-(dimethylamino)pyridine, picolinic acid and stannic chloride yields the title salt, (C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)], in which the Sn^IV atom is N,O-chelated by the picolinate ion in a cis-SnNOCl₄ octahedral geometry. The cation is linked to the anion by an N—H⋯O hydrogen bond.

Related literature

For 4-(dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato)stannate, see: Najafi et al. (2011 ).

Experimental

Crystal data

(C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)]
M_r = 505.77
Triclinic, $[P \overline 1]$
a = 7.6658 (2) Å
b = 9.8948 (4) Å
c = 13.5722 (6) Å
α = 69.485 (4)°
β = 83.159 (3)°
γ = 67.900 (3)°
V = 893.25 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.04 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, 2012 ) T_min = 0.580, T_max = 0.686
12966 measured reflections
4109 independent reflections
3744 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.049
S = 1.02
4109 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.87 (1)	1.93 (1)	2.802 (2)	176 (2)

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/S160053681201968X/bt5909sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201968X/bt5909Isup2.hkl

checkCIF report

Comment top

A previous study reported 4-(dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato)stannate, which was synthesized by the reaction of 4-(dimethylamino)pyridine, quinoline-2-carboxylic acid and stannic chloride in methanol (Najafi et al., 2011). The reaction with picolinic acid in place of quinoline-2-carboxylic acid yielded the analogous salt, (C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)] (Scheme I). The Sn^IV atom is N,O-chelated by the picolinate ion in a cis-SnNOCl₄ octahedral geometry (Fig. 1). The cation is linked to the anion by an N–H···O hydrogen bond (Table 1).

Related literature top

For 4-(dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato)stannate, see: Najafi et al. (2011).

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol), picolinic acid (0.12 g, 1 mmol) and 4-(dimethylamino)pyridine (0.12 g, 1 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Colorless 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of (C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(Dimethylamino)pyridinium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV) top

Crystal data top

(C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)]	Z = 2
M_r = 505.77	F(000) = 496
Triclinic, P1	D_x = 1.880 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6658 (2) Å	Cell parameters from 8614 reflections
b = 9.8948 (4) Å	θ = 2.4–27.5°
c = 13.5722 (6) Å	µ = 2.04 mm⁻¹
α = 69.485 (4)°	T = 100 K
β = 83.159 (3)°	Prism, colorless
γ = 67.900 (3)°	0.30 × 0.25 × 0.20 mm
V = 893.25 (6) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4109 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3744 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
T_min = 0.580, T_max = 0.686	l = −17→17
12966 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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0217P)² + 0.1127P] where P = (F_o² + 2F_c²)/3
4109 reflections	(Δ/σ)_max = 0.002
214 parameters	Δρ_max = 0.61 e Å⁻³
1 restraint	Δρ_min = −0.41 e Å⁻³

Crystal data top

(C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)]	γ = 67.900 (3)°
M_r = 505.77	V = 893.25 (6) Å³
Triclinic, P1	Z = 2
a = 7.6658 (2) Å	Mo Kα radiation
b = 9.8948 (4) Å	µ = 2.04 mm⁻¹
c = 13.5722 (6) Å	T = 100 K
α = 69.485 (4)°	0.30 × 0.25 × 0.20 mm
β = 83.159 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4109 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3744 reflections with I > 2σ(I)
T_min = 0.580, T_max = 0.686	R_int = 0.029
12966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	1 restraint
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.61 e Å⁻³
4109 reflections	Δρ_min = −0.41 e Å⁻³
214 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.471694 (16)	0.931155 (14)	0.787934 (10)	0.01225 (5)
Cl1	0.41910 (7)	1.16043 (5)	0.82535 (4)	0.01887 (11)
Cl2	0.63070 (7)	0.97801 (6)	0.62519 (4)	0.01884 (11)
Cl3	0.76267 (6)	0.79583 (6)	0.88640 (4)	0.01957 (11)
Cl4	0.16639 (6)	1.04910 (5)	0.70014 (4)	0.01687 (10)
O1	0.48413 (18)	0.72139 (15)	0.77597 (11)	0.0164 (3)
O2	0.3917 (2)	0.51987 (16)	0.84279 (12)	0.0231 (3)
N1	0.3269 (2)	0.83176 (18)	0.93069 (12)	0.0137 (3)
N2	0.6230 (2)	0.5870 (2)	0.61853 (14)	0.0184 (4)
H2	0.574 (3)	0.630 (3)	0.6665 (15)	0.038 (7)*
N3	0.8688 (2)	0.35910 (18)	0.40725 (13)	0.0153 (3)
C1	0.3977 (3)	0.6389 (2)	0.84580 (16)	0.0159 (4)
C2	0.3057 (3)	0.7014 (2)	0.93305 (15)	0.0155 (4)
C3	0.2055 (3)	0.6298 (2)	1.01141 (17)	0.0217 (5)
H3	0.1910	0.5382	1.0122	0.026*
C4	0.1268 (3)	0.6952 (3)	1.08887 (17)	0.0270 (5)
H4	0.0545	0.6500	1.1428	0.032*
C5	0.1535 (3)	0.8254 (3)	1.08742 (16)	0.0235 (5)
H5	0.1024	0.8694	1.1412	0.028*
C6	0.2552 (3)	0.8922 (2)	1.00731 (15)	0.0178 (4)
H6	0.2744	0.9819	1.0066	0.021*
C7	0.6389 (3)	0.4385 (2)	0.64189 (16)	0.0176 (4)
H7	0.5927	0.3883	0.7070	0.021*
C8	0.7198 (2)	0.3592 (2)	0.57414 (15)	0.0153 (4)
H8	0.7304	0.2546	0.5922	0.018*
C9	0.7888 (2)	0.4335 (2)	0.47584 (15)	0.0137 (4)
C10	0.7676 (3)	0.5896 (2)	0.45468 (16)	0.0159 (4)
H10	0.8102	0.6444	0.3900	0.019*
C11	0.6865 (3)	0.6614 (2)	0.52659 (17)	0.0183 (4)
H11	0.6745	0.7657	0.5117	0.022*
C12	0.8845 (3)	0.1993 (2)	0.42939 (17)	0.0213 (5)
H12A	0.9601	0.1329	0.4937	0.032*
H12B	0.9454	0.1647	0.3704	0.032*
H12C	0.7585	0.1933	0.4390	0.032*
C13	0.9392 (3)	0.4362 (2)	0.30663 (16)	0.0201 (4)
H13A	1.0157	0.4893	0.3186	0.030*
H13B	0.8327	0.5118	0.2599	0.030*
H13C	1.0164	0.3592	0.2741	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01423 (8)	0.01017 (8)	0.01266 (8)	−0.00471 (5)	0.00094 (5)	−0.00403 (5)
Cl1	0.0237 (2)	0.0125 (2)	0.0218 (3)	−0.00547 (19)	−0.00284 (19)	−0.0074 (2)
Cl2	0.0212 (2)	0.0168 (2)	0.0171 (3)	−0.00816 (19)	0.00602 (18)	−0.00436 (19)
Cl3	0.0165 (2)	0.0175 (2)	0.0221 (3)	−0.00282 (19)	−0.00390 (18)	−0.0058 (2)
Cl4	0.0166 (2)	0.0169 (2)	0.0167 (2)	−0.00586 (19)	−0.00196 (17)	−0.00459 (19)
O1	0.0222 (7)	0.0122 (7)	0.0173 (7)	−0.0088 (6)	0.0041 (5)	−0.0062 (6)
O2	0.0294 (8)	0.0166 (8)	0.0270 (9)	−0.0130 (6)	0.0004 (6)	−0.0063 (6)
N1	0.0137 (8)	0.0129 (8)	0.0121 (8)	−0.0034 (6)	−0.0013 (6)	−0.0025 (7)
N2	0.0170 (8)	0.0200 (9)	0.0193 (9)	−0.0035 (7)	−0.0013 (7)	−0.0105 (8)
N3	0.0178 (8)	0.0118 (8)	0.0167 (9)	−0.0054 (7)	0.0020 (6)	−0.0054 (7)
C1	0.0149 (9)	0.0134 (10)	0.0178 (10)	−0.0052 (8)	−0.0041 (7)	−0.0019 (8)
C2	0.0136 (9)	0.0131 (10)	0.0156 (10)	−0.0032 (8)	−0.0040 (7)	−0.0001 (8)
C3	0.0189 (10)	0.0203 (11)	0.0214 (11)	−0.0093 (8)	−0.0026 (8)	0.0020 (9)
C4	0.0186 (10)	0.0331 (13)	0.0181 (12)	−0.0088 (9)	0.0027 (8)	0.0032 (10)
C5	0.0190 (10)	0.0286 (12)	0.0143 (11)	−0.0009 (9)	−0.0011 (8)	−0.0050 (9)
C6	0.0168 (10)	0.0197 (11)	0.0133 (10)	−0.0028 (8)	−0.0017 (7)	−0.0047 (8)
C7	0.0144 (9)	0.0201 (11)	0.0168 (10)	−0.0071 (8)	−0.0009 (7)	−0.0031 (8)
C8	0.0138 (9)	0.0125 (10)	0.0177 (10)	−0.0052 (8)	−0.0010 (7)	−0.0018 (8)
C9	0.0105 (9)	0.0130 (10)	0.0165 (10)	−0.0035 (7)	−0.0027 (7)	−0.0036 (8)
C10	0.0174 (9)	0.0120 (10)	0.0179 (10)	−0.0060 (8)	−0.0029 (7)	−0.0027 (8)
C11	0.0177 (10)	0.0120 (10)	0.0244 (11)	−0.0036 (8)	−0.0062 (8)	−0.0048 (8)
C12	0.0227 (10)	0.0138 (10)	0.0289 (12)	−0.0058 (8)	0.0011 (9)	−0.0099 (9)
C13	0.0208 (10)	0.0208 (11)	0.0170 (11)	−0.0067 (9)	0.0030 (8)	−0.0059 (9)

Geometric parameters (Å, º) top

Sn1—O1	2.1041 (13)	C4—C5	1.372 (3)
Sn1—N1	2.2194 (16)	C4—H4	0.9500
Sn1—Cl1	2.3743 (5)	C5—C6	1.381 (3)
Sn1—Cl2	2.3761 (5)	C5—H5	0.9500
Sn1—Cl3	2.4006 (5)	C6—H6	0.9500
Sn1—Cl4	2.4277 (5)	C7—C8	1.359 (3)
O1—C1	1.311 (2)	C7—H7	0.9500
O2—C1	1.210 (2)	C8—C9	1.427 (3)
N1—C6	1.339 (2)	C8—H8	0.9500
N1—C2	1.348 (3)	C9—C10	1.416 (3)
N2—C11	1.348 (3)	C10—C11	1.361 (3)
N2—C7	1.350 (3)	C10—H10	0.9500
N2—H2	0.874 (10)	C11—H11	0.9500
N3—C9	1.338 (2)	C12—H12A	0.9800
N3—C12	1.462 (3)	C12—H12B	0.9800
N3—C13	1.464 (2)	C12—H12C	0.9800
C1—C2	1.506 (3)	C13—H13A	0.9800
C2—C3	1.382 (3)	C13—H13B	0.9800
C3—C4	1.386 (3)	C13—H13C	0.9800
C3—H3	0.9500

O1—Sn1—N1	75.84 (6)	C5—C4—H4	120.1
O1—Sn1—Cl1	169.89 (4)	C3—C4—H4	120.1
N1—Sn1—Cl1	94.27 (4)	C4—C5—C6	119.6 (2)
O1—Sn1—Cl2	88.75 (4)	C4—C5—H5	120.2
N1—Sn1—Cl2	164.57 (4)	C6—C5—H5	120.2
Cl1—Sn1—Cl2	101.090 (18)	N1—C6—C5	120.7 (2)
O1—Sn1—Cl3	89.31 (4)	N1—C6—H6	119.6
N1—Sn1—Cl3	88.57 (4)	C5—C6—H6	119.6
Cl1—Sn1—Cl3	92.581 (18)	N2—C7—C8	121.32 (19)
Cl2—Sn1—Cl3	92.190 (18)	N2—C7—H7	119.3
O1—Sn1—Cl4	87.20 (4)	C8—C7—H7	119.3
N1—Sn1—Cl4	86.38 (4)	C7—C8—C9	119.91 (19)
Cl1—Sn1—Cl4	90.124 (17)	C7—C8—H8	120.0
Cl2—Sn1—Cl4	92.055 (17)	C9—C8—H8	120.0
Cl3—Sn1—Cl4	174.439 (17)	N3—C9—C10	121.88 (18)
C1—O1—Sn1	119.22 (12)	N3—C9—C8	121.49 (18)
C6—N1—C2	120.02 (17)	C10—C9—C8	116.63 (18)
C6—N1—Sn1	126.65 (14)	C11—C10—C9	120.29 (19)
C2—N1—Sn1	113.24 (12)	C11—C10—H10	119.9
C11—N2—C7	120.66 (18)	C9—C10—H10	119.9
C11—N2—H2	122.3 (18)	N2—C11—C10	121.18 (19)
C7—N2—H2	117.0 (18)	N2—C11—H11	119.4
C9—N3—C12	120.98 (17)	C10—C11—H11	119.4
C9—N3—C13	121.09 (17)	N3—C12—H12A	109.5
C12—N3—C13	117.91 (16)	N3—C12—H12B	109.5
O2—C1—O1	123.64 (18)	H12A—C12—H12B	109.5
O2—C1—C2	121.19 (18)	N3—C12—H12C	109.5
O1—C1—C2	115.16 (17)	H12A—C12—H12C	109.5
N1—C2—C3	121.61 (19)	H12B—C12—H12C	109.5
N1—C2—C1	116.16 (17)	N3—C13—H13A	109.5
C3—C2—C1	122.22 (19)	N3—C13—H13B	109.5
C2—C3—C4	118.2 (2)	H13A—C13—H13B	109.5
C2—C3—H3	120.9	N3—C13—H13C	109.5
C4—C3—H3	120.9	H13A—C13—H13C	109.5
C5—C4—C3	119.8 (2)	H13B—C13—H13C	109.5

N1—Sn1—O1—C1	4.83 (13)	O1—C1—C2—N1	−1.6 (2)
Cl1—Sn1—O1—C1	−7.3 (3)	O2—C1—C2—C3	−2.2 (3)
Cl2—Sn1—O1—C1	−174.26 (13)	O1—C1—C2—C3	178.52 (17)
Cl3—Sn1—O1—C1	93.53 (13)	N1—C2—C3—C4	−0.3 (3)
Cl4—Sn1—O1—C1	−82.14 (13)	C1—C2—C3—C4	179.61 (17)
O1—Sn1—N1—C6	178.01 (16)	C2—C3—C4—C5	−1.5 (3)
Cl1—Sn1—N1—C6	−4.12 (15)	C3—C4—C5—C6	1.5 (3)
Cl2—Sn1—N1—C6	−178.59 (11)	C2—N1—C6—C5	−2.2 (3)
Cl3—Sn1—N1—C6	88.36 (15)	Sn1—N1—C6—C5	174.16 (13)
Cl4—Sn1—N1—C6	−93.97 (15)	C4—C5—C6—N1	0.4 (3)
O1—Sn1—N1—C2	−5.40 (12)	C11—N2—C7—C8	0.3 (3)
Cl1—Sn1—N1—C2	172.47 (12)	N2—C7—C8—C9	−0.4 (3)
Cl2—Sn1—N1—C2	−2.0 (2)	C12—N3—C9—C10	−178.27 (17)
Cl3—Sn1—N1—C2	−95.05 (12)	C13—N3—C9—C10	0.2 (3)
Cl4—Sn1—N1—C2	82.62 (12)	C12—N3—C9—C8	1.5 (3)
Sn1—O1—C1—O2	177.24 (15)	C13—N3—C9—C8	−179.96 (16)
Sn1—O1—C1—C2	−3.5 (2)	C7—C8—C9—N3	−179.87 (17)
C6—N1—C2—C3	2.2 (3)	C7—C8—C9—C10	−0.1 (3)
Sn1—N1—C2—C3	−174.69 (14)	N3—C9—C10—C11	−179.60 (17)
C6—N1—C2—C1	−177.72 (16)	C8—C9—C10—C11	0.6 (3)
Sn1—N1—C2—C1	5.44 (19)	C7—N2—C11—C10	0.3 (3)
O2—C1—C2—N1	177.67 (17)	C9—C10—C11—N2	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.87 (1)	1.93 (1)	2.802 (2)	176 (2)

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)[SnCl₄(C₆H₄NO₂)]
M_r	505.77
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.6658 (2), 9.8948 (4), 13.5722 (6)
α, β, γ (°)	69.485 (4), 83.159 (3), 67.900 (3)
V (Å³)	893.25 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.04
Crystal size (mm)	0.30 × 0.25 × 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	0.580, 0.686
No. of measured, independent and observed [I > 2σ(I)] reflections	12966, 4109, 3744
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.049, 1.02
No. of reflections	4109
No. of parameters	214
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)	0.61, −0.41

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···O1	0.87 (1)	1.93 (1)	2.802 (2)	176 (2)

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

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