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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Aug 11;67(Pt 9):m1224. doi: 10.1107/S1600536811031473

4-(Dimethyl­amino)­pyridinium tetra­chlorido(quinoline-2-carboxyl­ato-κ2 N,O)stannate(IV)

Ezzatollah Najafi a, Mostafa M Amini a, Seik Weng Ng b,c,*
PMCID: PMC3200806  PMID: 22058853

Abstract

In the title salt, (C7H11N2)[SnCl4(C10H6NO2)], the SnIV atom is chelated by the N,O-bidentate carboxyl­ate ions and four chloride ions, showing a distorted octa­hedral SnNOCl4 coordination. In the crystal, the cation and anion are linked by a pyridinium–carboxyl­ate N—H⋯O hydrogen bond.

Related literature

For a related ammonium tetra­chlorido(pyridine-2-carboxyl­ato)stannate(IV), see: Najafi et al. (2011).graphic file with name e-67-m1224-scheme1.jpg

Experimental

Crystal data

  • (C7H11N2)[SnCl4(C10H6NO2)]

  • M r = 555.83

  • Triclinic, Inline graphic

  • a = 8.6681 (3) Å

  • b = 8.8407 (4) Å

  • c = 14.4447 (5) Å

  • α = 96.721 (3)°

  • β = 91.924 (3)°

  • γ = 108.038 (4)°

  • V = 1042.43 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.76 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T min = 0.621, T max = 0.844

  • 8056 measured reflections

  • 4610 independent reflections

  • 4202 reflections with I > 2σ(I)

  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021

  • wR(F 2) = 0.047

  • S = 1.06

  • 4610 reflections

  • 250 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.49 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010); 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).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031473/xu5284sup1.cif

e-67-m1224-sup1.cif (19.7KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031473/xu5284Isup2.hkl

e-67-m1224-Isup2.hkl (225.8KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O1 0.87 (1) 1.98 (1) 2.816 (2) 160 (2)

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have recently synthesized some ammonium tetrachlorido(carboxylato)stannates; in a recent study, we reacted stannic chloride with pyridine-2-carboxylic acid and triethylamine to yield the chelated stannate salt (Najafi et al., 2011). The use of quinoline-2-carboxylic acid and 4-dimethyaminopyridine yielded the expected dimethylaminopyridinium stannate in which the amine is protonated on the aromatic nitrogen atom (Scheme I, Fig. 1). The SnIV atom is chelated by the N,O-bidentate carboxylate ligand and four chloride ions, and shows octahedral SnNOCl4 coordination at the metal atom. The cation and anion are linked an N–Hpyridinium···O hydrogen bond (Table 1).

Experimental

Stannic chloride pentahydrate (1 mmol), quinoline-2-carboxylic acid (1 mmol) and 4-dimethylaminopyridine (1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

The ammonium H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; its temperature factor was refined.

Omitted from the refinement was the (0 1 0) reflection.

Figures

Fig. 1.

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of (C7H11N2)[SnCl4(C10H6NO2)] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(C7H11N2)[SnCl4(C10H6NO2)] Z = 2
Mr = 555.83 F(000) = 548
Triclinic, P1 Dx = 1.771 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 8.6681 (3) Å Cell parameters from 5833 reflections
b = 8.8407 (4) Å θ = 2.4–29.2°
c = 14.4447 (5) Å µ = 1.76 mm1
α = 96.721 (3)° T = 100 K
β = 91.924 (3)° Block, colorless
γ = 108.038 (4)° 0.30 × 0.20 × 0.10 mm
V = 1042.43 (7) Å3

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector 4610 independent reflections
Radiation source: SuperNova (Mo) X-ray Source 4202 reflections with I > 2σ(I)
Mirror Rint = 0.022
Detector resolution: 10.4041 pixels mm-1 θmax = 27.5°, θmin = 2.5°
ω scans h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) k = −11→11
Tmin = 0.621, Tmax = 0.844 l = −18→18
8056 measured reflections

Refinement

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)] = 0.021 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047 H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0181P)2 + 0.127P] where P = (Fo2 + 2Fc2)/3
4610 reflections (Δ/σ)max = 0.001
250 parameters Δρmax = 0.52 e Å3
1 restraint Δρmin = −0.49 e Å3

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

x y z Uiso*/Ueq
Sn1 0.361135 (16) 0.258730 (15) 0.271428 (9) 0.01232 (5)
Cl1 0.16903 (6) 0.37830 (6) 0.33361 (4) 0.02211 (12)
Cl2 0.13953 (6) 0.04597 (6) 0.18599 (3) 0.01824 (11)
Cl3 0.41373 (6) 0.41174 (6) 0.14341 (4) 0.02133 (11)
Cl4 0.58090 (6) 0.44245 (6) 0.37084 (4) 0.02246 (12)
O1 0.51697 (17) 0.14313 (16) 0.21142 (9) 0.0165 (3)
O2 0.57573 (18) −0.08559 (17) 0.19327 (10) 0.0207 (3)
N1 0.36250 (19) 0.06808 (18) 0.36458 (10) 0.0124 (3)
N2 1.0685 (2) 0.3405 (2) −0.12106 (11) 0.0173 (4)
N3 0.7058 (2) 0.2281 (2) 0.05939 (12) 0.0203 (4)
H3 0.629 (2) 0.206 (3) 0.0979 (13) 0.024 (6)*
C1 0.2921 (2) 0.0400 (2) 0.44784 (13) 0.0134 (4)
C2 0.2404 (2) 0.1582 (2) 0.49972 (13) 0.0173 (4)
H2 0.2535 0.2582 0.4777 0.021*
C3 0.1712 (3) 0.1279 (3) 0.58221 (14) 0.0203 (5)
H3A 0.1369 0.2080 0.6172 0.024*
C4 0.1499 (3) −0.0194 (3) 0.61614 (14) 0.0219 (5)
H4 0.0987 −0.0389 0.6726 0.026*
C5 0.2022 (2) −0.1341 (3) 0.56843 (14) 0.0194 (5)
H5 0.1888 −0.2327 0.5923 0.023*
C6 0.2768 (2) −0.1071 (2) 0.48305 (13) 0.0158 (4)
C7 0.3379 (2) −0.2201 (2) 0.43302 (14) 0.0172 (4)
H7 0.3269 −0.3199 0.4550 0.021*
C8 0.4130 (2) −0.1860 (2) 0.35297 (13) 0.0164 (4)
H8 0.4577 −0.2598 0.3196 0.020*
C9 0.4230 (2) −0.0400 (2) 0.32101 (13) 0.0133 (4)
C10 0.5114 (2) 0.0037 (2) 0.23433 (13) 0.0145 (4)
C11 0.9504 (2) 0.3054 (2) −0.06169 (13) 0.0143 (4)
C12 0.9714 (3) 0.2416 (2) 0.02178 (14) 0.0184 (4)
H12 1.0717 0.2248 0.0375 0.022*
C13 0.8486 (3) 0.2047 (2) 0.07897 (14) 0.0205 (5)
H13 0.8638 0.1612 0.1344 0.025*
C14 0.6811 (3) 0.2898 (2) −0.01880 (14) 0.0199 (5)
H14 0.5797 0.3062 −0.0316 0.024*
C15 0.7983 (2) 0.3288 (2) −0.07943 (14) 0.0166 (4)
H15 0.7784 0.3720 −0.1341 0.020*
C16 1.2127 (3) 0.2906 (3) −0.10898 (16) 0.0242 (5)
H16A 1.2761 0.3488 −0.0511 0.036*
H16B 1.2794 0.3146 −0.1621 0.036*
H16C 1.1793 0.1750 −0.1057 0.036*
C17 1.0413 (3) 0.3978 (3) −0.20898 (14) 0.0258 (5)
H17A 0.9928 0.4840 −0.1971 0.039*
H17B 0.9676 0.3091 −0.2522 0.039*
H17C 1.1454 0.4388 −0.2367 0.039*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Sn1 0.01240 (7) 0.01035 (8) 0.01461 (8) 0.00357 (6) 0.00258 (5) 0.00280 (5)
Cl1 0.0238 (3) 0.0179 (3) 0.0275 (3) 0.0104 (2) 0.0071 (2) 0.0023 (2)
Cl2 0.0183 (3) 0.0146 (2) 0.0197 (2) 0.0034 (2) −0.0038 (2) 0.00033 (19)
Cl3 0.0229 (3) 0.0214 (3) 0.0235 (3) 0.0086 (2) 0.0061 (2) 0.0125 (2)
Cl4 0.0208 (3) 0.0168 (3) 0.0243 (3) −0.0010 (2) −0.0032 (2) 0.0012 (2)
O1 0.0185 (7) 0.0168 (7) 0.0173 (7) 0.0084 (6) 0.0074 (6) 0.0045 (6)
O2 0.0244 (8) 0.0229 (8) 0.0197 (8) 0.0145 (7) 0.0054 (6) 0.0025 (6)
N1 0.0110 (8) 0.0117 (8) 0.0134 (8) 0.0021 (7) 0.0000 (7) 0.0015 (6)
N2 0.0155 (9) 0.0163 (9) 0.0181 (9) 0.0026 (7) 0.0042 (7) 0.0005 (7)
N3 0.0200 (10) 0.0245 (10) 0.0175 (9) 0.0072 (8) 0.0089 (8) 0.0042 (7)
C1 0.0110 (9) 0.0149 (10) 0.0122 (9) 0.0010 (8) −0.0007 (8) 0.0027 (8)
C2 0.0167 (10) 0.0170 (11) 0.0171 (10) 0.0039 (9) −0.0004 (8) 0.0024 (8)
C3 0.0164 (11) 0.0256 (12) 0.0177 (10) 0.0062 (9) 0.0013 (9) −0.0013 (9)
C4 0.0159 (11) 0.0329 (13) 0.0134 (10) 0.0027 (10) 0.0022 (8) 0.0030 (9)
C5 0.0159 (10) 0.0194 (11) 0.0183 (10) −0.0027 (9) −0.0010 (9) 0.0075 (9)
C6 0.0126 (10) 0.0164 (10) 0.0155 (10) 0.0006 (8) −0.0029 (8) 0.0032 (8)
C7 0.0187 (11) 0.0117 (10) 0.0187 (10) 0.0012 (9) −0.0048 (9) 0.0034 (8)
C8 0.0166 (10) 0.0146 (10) 0.0169 (10) 0.0052 (9) −0.0034 (8) −0.0013 (8)
C9 0.0113 (9) 0.0139 (10) 0.0136 (10) 0.0033 (8) −0.0012 (8) 0.0003 (8)
C10 0.0120 (10) 0.0171 (10) 0.0136 (10) 0.0039 (8) −0.0016 (8) 0.0019 (8)
C11 0.0157 (10) 0.0098 (9) 0.0154 (10) 0.0021 (8) 0.0023 (8) −0.0022 (7)
C12 0.0170 (10) 0.0204 (11) 0.0193 (10) 0.0084 (9) 0.0006 (9) 0.0020 (8)
C13 0.0245 (12) 0.0204 (11) 0.0179 (10) 0.0077 (10) 0.0017 (9) 0.0062 (8)
C14 0.0178 (11) 0.0230 (12) 0.0198 (11) 0.0096 (9) 0.0000 (9) −0.0020 (9)
C15 0.0195 (11) 0.0174 (10) 0.0143 (10) 0.0086 (9) −0.0002 (8) 0.0002 (8)
C16 0.0132 (10) 0.0261 (12) 0.0317 (12) 0.0054 (9) 0.0070 (9) −0.0015 (10)
C17 0.0333 (13) 0.0236 (12) 0.0204 (11) 0.0065 (10) 0.0118 (10) 0.0068 (9)

Geometric parameters (Å, °)

Sn1—O1 2.0848 (13) C4—H4 0.9500
Sn1—N1 2.2790 (16) C5—C6 1.422 (3)
Sn1—Cl1 2.3802 (5) C5—H5 0.9500
Sn1—Cl4 2.3840 (5) C6—C7 1.409 (3)
Sn1—Cl3 2.3912 (5) C7—C8 1.365 (3)
Sn1—Cl2 2.4106 (5) C7—H7 0.9500
O1—C10 1.301 (2) C8—C9 1.400 (3)
O2—C10 1.213 (2) C8—H8 0.9500
N1—C9 1.333 (2) C9—C10 1.516 (3)
N1—C1 1.381 (2) C11—C15 1.416 (3)
N2—C11 1.343 (2) C11—C12 1.419 (3)
N2—C17 1.459 (3) C12—C13 1.353 (3)
N2—C16 1.460 (3) C12—H12 0.9500
N3—C13 1.343 (3) C13—H13 0.9500
N3—C14 1.348 (3) C14—C15 1.353 (3)
N3—H3 0.869 (9) C14—H14 0.9500
C1—C2 1.408 (3) C15—H15 0.9500
C1—C6 1.421 (3) C16—H16A 0.9800
C2—C3 1.369 (3) C16—H16B 0.9800
C2—H2 0.9500 C16—H16C 0.9800
C3—C4 1.406 (3) C17—H17A 0.9800
C3—H3A 0.9500 C17—H17B 0.9800
C4—C5 1.360 (3) C17—H17C 0.9800
O1—Sn1—N1 75.24 (5) C7—C6—C5 122.27 (19)
O1—Sn1—Cl1 176.27 (4) C1—C6—C5 118.72 (19)
N1—Sn1—Cl1 104.74 (4) C8—C7—C6 119.87 (18)
O1—Sn1—Cl4 90.93 (4) C8—C7—H7 120.1
N1—Sn1—Cl4 88.46 (4) C6—C7—H7 120.1
Cl1—Sn1—Cl4 92.797 (19) C7—C8—C9 118.64 (19)
O1—Sn1—Cl3 85.08 (4) C7—C8—H8 120.7
N1—Sn1—Cl3 160.21 (4) C9—C8—H8 120.7
Cl1—Sn1—Cl3 94.762 (18) N1—C9—C8 123.44 (17)
Cl4—Sn1—Cl3 93.991 (19) N1—C9—C10 116.83 (17)
O1—Sn1—Cl2 87.29 (4) C8—C9—C10 119.70 (17)
N1—Sn1—Cl2 83.40 (4) O2—C10—O1 124.30 (18)
Cl1—Sn1—Cl2 89.002 (18) O2—C10—C9 120.59 (18)
Cl4—Sn1—Cl2 171.852 (17) O1—C10—C9 115.05 (17)
Cl3—Sn1—Cl2 93.779 (18) N2—C11—C15 121.88 (18)
C10—O1—Sn1 118.81 (12) N2—C11—C12 121.52 (19)
C9—N1—C1 119.22 (16) C15—C11—C12 116.60 (18)
C9—N1—Sn1 110.22 (12) C13—C12—C11 119.88 (19)
C1—N1—Sn1 129.82 (13) C13—C12—H12 120.1
C11—N2—C17 120.69 (18) C11—C12—H12 120.1
C11—N2—C16 120.42 (17) N3—C13—C12 121.67 (19)
C17—N2—C16 117.65 (17) N3—C13—H13 119.2
C13—N3—C14 120.35 (18) C12—C13—H13 119.2
C13—N3—H3 120.3 (15) N3—C14—C15 121.2 (2)
C14—N3—H3 119.4 (15) N3—C14—H14 119.4
N1—C1—C2 120.50 (17) C15—C14—H14 119.4
N1—C1—C6 119.72 (17) C14—C15—C11 120.29 (19)
C2—C1—C6 119.74 (17) C14—C15—H15 119.9
C3—C2—C1 119.50 (19) C11—C15—H15 119.9
C3—C2—H2 120.2 N2—C16—H16A 109.5
C1—C2—H2 120.2 N2—C16—H16B 109.5
C2—C3—C4 121.3 (2) H16A—C16—H16B 109.5
C2—C3—H3A 119.3 N2—C16—H16C 109.5
C4—C3—H3A 119.3 H16A—C16—H16C 109.5
C5—C4—C3 120.29 (19) H16B—C16—H16C 109.5
C5—C4—H4 119.9 N2—C17—H17A 109.5
C3—C4—H4 119.9 N2—C17—H17B 109.5
C4—C5—C6 120.34 (19) H17A—C17—H17B 109.5
C4—C5—H5 119.8 N2—C17—H17C 109.5
C6—C5—H5 119.8 H17A—C17—H17C 109.5
C7—C6—C1 119.00 (17) H17B—C17—H17C 109.5
N1—Sn1—O1—C10 17.16 (14) C4—C5—C6—C1 −1.4 (3)
Cl4—Sn1—O1—C10 105.32 (14) C1—C6—C7—C8 1.2 (3)
Cl3—Sn1—O1—C10 −160.75 (14) C5—C6—C7—C8 −177.90 (19)
Cl2—Sn1—O1—C10 −66.72 (14) C6—C7—C8—C9 −1.9 (3)
O1—Sn1—N1—C9 −16.03 (12) C1—N1—C9—C8 2.9 (3)
Cl1—Sn1—N1—C9 160.11 (12) Sn1—N1—C9—C8 −168.24 (16)
Cl4—Sn1—N1—C9 −107.40 (12) C1—N1—C9—C10 −174.97 (16)
Cl3—Sn1—N1—C9 −9.9 (2) Sn1—N1—C9—C10 13.9 (2)
Cl2—Sn1—N1—C9 72.90 (12) C7—C8—C9—N1 −0.2 (3)
O1—Sn1—N1—C1 174.03 (17) C7—C8—C9—C10 177.68 (17)
Cl1—Sn1—N1—C1 −9.83 (16) Sn1—O1—C10—O2 167.37 (15)
Cl4—Sn1—N1—C1 82.65 (16) Sn1—O1—C10—C9 −15.3 (2)
Cl3—Sn1—N1—C1 −179.84 (11) N1—C9—C10—O2 176.83 (18)
Cl2—Sn1—N1—C1 −97.05 (16) C8—C9—C10—O2 −1.1 (3)
C9—N1—C1—C2 174.22 (18) N1—C9—C10—O1 −0.6 (3)
Sn1—N1—C1—C2 −16.6 (3) C8—C9—C10—O1 −178.61 (17)
C9—N1—C1—C6 −3.6 (3) C17—N2—C11—C15 −2.8 (3)
Sn1—N1—C1—C6 165.62 (14) C16—N2—C11—C15 −169.76 (18)
N1—C1—C2—C3 −179.86 (18) C17—N2—C11—C12 176.65 (18)
C6—C1—C2—C3 −2.1 (3) C16—N2—C11—C12 9.6 (3)
C1—C2—C3—C4 −0.3 (3) N2—C11—C12—C13 −178.67 (19)
C2—C3—C4—C5 1.8 (3) C15—C11—C12—C13 0.8 (3)
C3—C4—C5—C6 −0.9 (3) C14—N3—C13—C12 0.0 (3)
N1—C1—C6—C7 1.6 (3) C11—C12—C13—N3 −0.5 (3)
C2—C1—C6—C7 −176.23 (18) C13—N3—C14—C15 0.3 (3)
N1—C1—C6—C5 −179.32 (17) N3—C14—C15—C11 −0.1 (3)
C2—C1—C6—C5 2.9 (3) N2—C11—C15—C14 178.95 (19)
C4—C5—C6—C7 177.70 (19) C12—C11—C15—C14 −0.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N3—H3···O1 0.87 (1) 1.98 (1) 2.816 (2) 160 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5284).

References

  1. Agilent (2010). CrysAlis PRO Agilent Technologies, Yarnton, England.
  2. Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  3. Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m351. [DOI] [PMC free article] [PubMed]
  4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  5. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031473/xu5284sup1.cif

e-67-m1224-sup1.cif (19.7KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031473/xu5284Isup2.hkl

e-67-m1224-Isup2.hkl (225.8KB, hkl)

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


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