metal-organic compounds
10-Hydroxybenzo[h]quinolin-1-ium tetrachlorido(pyridine-2-carboxylato-κ2N,O)stannate(IV) methanol monosolvate
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
The reaction of 4-(dimethylamino)pyridine, picolinic acid and stannic chloride yields the title monosolvated salt, (C13H10NO)[SnCl4(C6H4NO2)]·CH3OH. The SnIV atom is N,O-chelated by the picolinate ion in a cis-SnNOCl4 octahedral geometry. The cation is linked to the methanol solvent molecule by an O—H⋯O hydrogen bond; the solvent molecule itself is a hydrogen-bond donor to the uncoordinating carboxylate O atom of the anion. The cations and anions are linked by weak N—H⋯Cl interactions, forming a chain running along the b axis.
Related literature
For a tetrachlorido(pyridine-2-carboxylato)stannate(IV), see: Najafi et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell 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
10.1107/S1600536812019605/hg5222sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812019605/hg5222Isup2.hkl
Stannic chloride pentahydrate (0.35 g, 1 mmol), picolinic acid (0.12 g, 1 mmol) and 10-hydroxybenzo[h]quinoline (0.20 g, 1 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Yellow crystals were collected from the side arm after several days.
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
in the riding model approximation.The hydroxy and ammonium H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 and N–H 0.88±0.01 Å; their temperature factors were was refined.
Data collection: CrysAlis PRO (Agilent, 2012); cell
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).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (C13H10NO)[SnCl4(C6H4NO2)].CH3OH at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
(C13H10NO)[SnCl4(C6H4NO2)]·CH4O | F(000) = 2416 |
Mr = 610.85 | Dx = 1.761 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6804 reflections |
a = 31.5065 (11) Å | θ = 2.6–27.5° |
b = 8.0802 (2) Å | µ = 1.60 mm−1 |
c = 20.0948 (9) Å | T = 100 K |
β = 115.722 (5)° | Prism, yellow |
V = 4608.8 (3) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 8 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5326 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 4445 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.6° |
ω scan | h = −29→40 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −10→10 |
Tmin = 0.645, Tmax = 0.856 | l = −26→16 |
15316 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0262P)2 + 2.9883P] where P = (Fo2 + 2Fc2)/3 |
5326 reflections | (Δ/σ)max = 0.001 |
293 parameters | Δρmax = 0.51 e Å−3 |
3 restraints | Δρmin = −0.44 e Å−3 |
(C13H10NO)[SnCl4(C6H4NO2)]·CH4O | V = 4608.8 (3) Å3 |
Mr = 610.85 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 31.5065 (11) Å | µ = 1.60 mm−1 |
b = 8.0802 (2) Å | T = 100 K |
c = 20.0948 (9) Å | 0.30 × 0.20 × 0.10 mm |
β = 115.722 (5)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5326 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 4445 reflections with I > 2σ(I) |
Tmin = 0.645, Tmax = 0.856 | Rint = 0.033 |
15316 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 3 restraints |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.51 e Å−3 |
5326 reflections | Δρmin = −0.44 e Å−3 |
293 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.341644 (5) | 0.660077 (19) | 0.666671 (10) | 0.01289 (6) | |
Cl1 | 0.37922 (2) | 0.39689 (7) | 0.68079 (4) | 0.02026 (14) | |
Cl2 | 0.40850 (2) | 0.82509 (7) | 0.68449 (4) | 0.02084 (15) | |
Cl3 | 0.31336 (2) | 0.66098 (8) | 0.53578 (4) | 0.02510 (15) | |
Cl4 | 0.36197 (2) | 0.66555 (8) | 0.79760 (4) | 0.02179 (15) | |
O1 | 0.27693 (5) | 0.5575 (2) | 0.65110 (10) | 0.0169 (4) | |
O2 | 0.20485 (6) | 0.6113 (2) | 0.64027 (11) | 0.0225 (4) | |
O3 | 0.07905 (6) | 0.2706 (2) | 0.53486 (11) | 0.0217 (4) | |
O4 | 0.16051 (6) | 0.3577 (2) | 0.54923 (12) | 0.0238 (4) | |
N1 | 0.29836 (7) | 0.8782 (2) | 0.66282 (12) | 0.0144 (4) | |
N2 | 0.02661 (7) | 0.1368 (3) | 0.58997 (13) | 0.0172 (5) | |
C1 | 0.24389 (8) | 0.6557 (3) | 0.64886 (14) | 0.0153 (5) | |
C2 | 0.25594 (8) | 0.8378 (3) | 0.65863 (14) | 0.0148 (5) | |
C3 | 0.22558 (9) | 0.9549 (3) | 0.66296 (15) | 0.0191 (6) | |
H3A | 0.1957 | 0.9238 | 0.6599 | 0.023* | |
C4 | 0.23938 (9) | 1.1189 (3) | 0.67188 (16) | 0.0215 (6) | |
H4A | 0.2192 | 1.2022 | 0.6753 | 0.026* | |
C5 | 0.28285 (10) | 1.1601 (3) | 0.67575 (18) | 0.0253 (7) | |
H5 | 0.2928 | 1.2723 | 0.6813 | 0.030* | |
C6 | 0.31165 (9) | 1.0370 (3) | 0.67148 (16) | 0.0209 (6) | |
H6 | 0.3418 | 1.0654 | 0.6748 | 0.025* | |
C7 | 0.02266 (9) | 0.0482 (3) | 0.64277 (15) | 0.0200 (6) | |
H7 | 0.0501 | 0.0137 | 0.6846 | 0.024* | |
C8 | −0.02144 (9) | 0.0061 (3) | 0.63690 (16) | 0.0207 (6) | |
H8 | −0.0246 | −0.0580 | 0.6741 | 0.025* | |
C9 | −0.06052 (9) | 0.0593 (3) | 0.57607 (16) | 0.0192 (6) | |
H9 | −0.0910 | 0.0315 | 0.5714 | 0.023* | |
C10 | −0.05622 (9) | 0.1538 (3) | 0.52073 (15) | 0.0173 (5) | |
C11 | −0.09634 (9) | 0.2137 (3) | 0.45798 (16) | 0.0214 (6) | |
H11 | −0.1271 | 0.1894 | 0.4528 | 0.026* | |
C12 | −0.09079 (9) | 0.3046 (3) | 0.40608 (16) | 0.0228 (6) | |
H12 | −0.1180 | 0.3440 | 0.3650 | 0.027* | |
C13 | −0.04506 (9) | 0.3436 (3) | 0.41098 (15) | 0.0191 (6) | |
C14 | −0.04056 (9) | 0.4373 (3) | 0.35614 (16) | 0.0236 (6) | |
H14 | −0.0680 | 0.4748 | 0.3149 | 0.028* | |
C15 | 0.00334 (9) | 0.4759 (3) | 0.36123 (16) | 0.0240 (6) | |
H15 | 0.0059 | 0.5400 | 0.3235 | 0.029* | |
C16 | 0.04405 (9) | 0.4220 (3) | 0.42113 (16) | 0.0208 (6) | |
H16 | 0.0741 | 0.4495 | 0.4240 | 0.025* | |
C17 | 0.04076 (9) | 0.3285 (3) | 0.47630 (15) | 0.0172 (5) | |
C18 | −0.00405 (9) | 0.2878 (3) | 0.47287 (15) | 0.0166 (5) | |
C19 | −0.01061 (8) | 0.1925 (3) | 0.52815 (15) | 0.0153 (5) | |
C20 | 0.18022 (11) | 0.3508 (4) | 0.49717 (18) | 0.0330 (7) | |
H20A | 0.1712 | 0.4503 | 0.4662 | 0.050* | |
H20B | 0.1683 | 0.2525 | 0.4659 | 0.050* | |
H20C | 0.2146 | 0.3448 | 0.5237 | 0.050* | |
H2 | 0.0542 (6) | 0.171 (3) | 0.5956 (17) | 0.027 (8)* | |
H3 | 0.1041 (7) | 0.306 (4) | 0.5351 (19) | 0.042 (10)* | |
H4 | 0.1730 (9) | 0.434 (2) | 0.5790 (13) | 0.021 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01130 (9) | 0.01287 (9) | 0.01497 (11) | −0.00094 (7) | 0.00613 (7) | −0.00093 (7) |
Cl1 | 0.0175 (3) | 0.0155 (3) | 0.0278 (4) | 0.0006 (3) | 0.0098 (3) | −0.0006 (3) |
Cl2 | 0.0182 (3) | 0.0206 (3) | 0.0289 (4) | −0.0060 (3) | 0.0151 (3) | −0.0059 (3) |
Cl3 | 0.0224 (3) | 0.0360 (4) | 0.0157 (4) | 0.0055 (3) | 0.0071 (3) | −0.0004 (3) |
Cl4 | 0.0147 (3) | 0.0370 (4) | 0.0143 (3) | 0.0024 (3) | 0.0068 (3) | 0.0010 (3) |
O1 | 0.0114 (8) | 0.0143 (8) | 0.0242 (11) | −0.0025 (7) | 0.0072 (8) | −0.0018 (7) |
O2 | 0.0135 (9) | 0.0271 (10) | 0.0276 (12) | −0.0053 (8) | 0.0096 (9) | −0.0072 (9) |
O3 | 0.0120 (9) | 0.0288 (10) | 0.0226 (12) | −0.0037 (8) | 0.0058 (8) | 0.0051 (8) |
O4 | 0.0198 (10) | 0.0308 (11) | 0.0220 (12) | −0.0108 (9) | 0.0101 (9) | −0.0093 (9) |
N1 | 0.0184 (10) | 0.0129 (10) | 0.0136 (12) | 0.0004 (9) | 0.0084 (9) | 0.0013 (9) |
N2 | 0.0138 (10) | 0.0201 (11) | 0.0179 (13) | −0.0030 (9) | 0.0070 (10) | −0.0010 (9) |
C1 | 0.0141 (12) | 0.0193 (12) | 0.0118 (14) | −0.0012 (10) | 0.0050 (11) | −0.0017 (10) |
C2 | 0.0147 (12) | 0.0179 (12) | 0.0106 (13) | −0.0003 (10) | 0.0045 (11) | −0.0011 (10) |
C3 | 0.0147 (12) | 0.0247 (14) | 0.0179 (15) | 0.0033 (11) | 0.0069 (11) | 0.0009 (11) |
C4 | 0.0242 (14) | 0.0214 (13) | 0.0218 (17) | 0.0083 (12) | 0.0128 (13) | 0.0048 (12) |
C5 | 0.0342 (16) | 0.0137 (13) | 0.0355 (19) | 0.0010 (12) | 0.0221 (15) | 0.0026 (12) |
C6 | 0.0221 (13) | 0.0178 (12) | 0.0293 (18) | −0.0016 (11) | 0.0173 (13) | 0.0020 (11) |
C7 | 0.0200 (13) | 0.0223 (13) | 0.0164 (15) | −0.0016 (11) | 0.0067 (12) | −0.0002 (11) |
C8 | 0.0215 (13) | 0.0229 (13) | 0.0198 (16) | −0.0015 (12) | 0.0110 (12) | 0.0002 (12) |
C9 | 0.0161 (12) | 0.0232 (13) | 0.0221 (16) | −0.0039 (11) | 0.0118 (12) | −0.0057 (11) |
C10 | 0.0161 (12) | 0.0194 (13) | 0.0168 (15) | −0.0009 (11) | 0.0074 (11) | −0.0043 (11) |
C11 | 0.0118 (12) | 0.0288 (14) | 0.0238 (17) | −0.0021 (11) | 0.0079 (12) | −0.0063 (12) |
C12 | 0.0153 (13) | 0.0290 (14) | 0.0182 (16) | 0.0006 (11) | 0.0017 (12) | 0.0000 (12) |
C13 | 0.0180 (13) | 0.0210 (13) | 0.0167 (15) | −0.0010 (11) | 0.0062 (12) | −0.0013 (11) |
C14 | 0.0186 (13) | 0.0282 (15) | 0.0191 (16) | 0.0016 (12) | 0.0036 (12) | 0.0033 (12) |
C15 | 0.0261 (14) | 0.0266 (14) | 0.0183 (16) | −0.0019 (12) | 0.0087 (13) | 0.0041 (12) |
C16 | 0.0175 (13) | 0.0250 (14) | 0.0217 (17) | −0.0048 (11) | 0.0101 (12) | −0.0027 (12) |
C17 | 0.0152 (12) | 0.0174 (12) | 0.0163 (15) | −0.0022 (10) | 0.0044 (11) | −0.0035 (11) |
C18 | 0.0155 (12) | 0.0159 (12) | 0.0169 (15) | −0.0036 (10) | 0.0056 (11) | −0.0038 (11) |
C19 | 0.0134 (12) | 0.0160 (12) | 0.0150 (14) | −0.0023 (10) | 0.0047 (11) | −0.0046 (10) |
C20 | 0.0347 (17) | 0.0435 (18) | 0.0256 (19) | −0.0095 (14) | 0.0175 (15) | −0.0087 (14) |
Sn1—O1 | 2.0949 (15) | C7—C8 | 1.385 (3) |
Sn1—N1 | 2.2092 (19) | C7—H7 | 0.9500 |
Sn1—Cl3 | 2.3828 (7) | C8—C9 | 1.374 (4) |
Sn1—Cl2 | 2.3851 (6) | C8—H8 | 0.9500 |
Sn1—Cl1 | 2.3903 (6) | C9—C10 | 1.403 (4) |
Sn1—Cl4 | 2.4231 (7) | C9—H9 | 0.9500 |
O1—C1 | 1.294 (3) | C10—C19 | 1.414 (3) |
O2—C1 | 1.220 (3) | C10—C11 | 1.428 (4) |
O3—C17 | 1.352 (3) | C11—C12 | 1.347 (4) |
O3—H3 | 0.835 (10) | C11—H11 | 0.9500 |
O4—C20 | 1.431 (3) | C12—C13 | 1.436 (3) |
O4—H4 | 0.831 (10) | C12—H12 | 0.9500 |
N1—C6 | 1.338 (3) | C13—C14 | 1.394 (4) |
N1—C2 | 1.342 (3) | C13—C18 | 1.423 (4) |
N2—C7 | 1.330 (3) | C14—C15 | 1.377 (3) |
N2—C19 | 1.363 (3) | C14—H14 | 0.9500 |
N2—H2 | 0.870 (10) | C15—C16 | 1.394 (4) |
C1—C2 | 1.511 (3) | C15—H15 | 0.9500 |
C2—C3 | 1.375 (3) | C16—C17 | 1.382 (4) |
C3—C4 | 1.381 (4) | C16—H16 | 0.9500 |
C3—H3A | 0.9500 | C17—C18 | 1.422 (3) |
C4—C5 | 1.378 (4) | C18—C19 | 1.438 (3) |
C4—H4A | 0.9500 | C20—H20A | 0.9800 |
C5—C6 | 1.373 (3) | C20—H20B | 0.9800 |
C5—H5 | 0.9500 | C20—H20C | 0.9800 |
C6—H6 | 0.9500 | ||
O1—Sn1—N1 | 76.37 (7) | C8—C7—H7 | 119.9 |
O1—Sn1—Cl3 | 87.87 (5) | C9—C8—C7 | 118.5 (2) |
N1—Sn1—Cl3 | 91.69 (6) | C9—C8—H8 | 120.7 |
O1—Sn1—Cl2 | 169.28 (5) | C7—C8—H8 | 120.7 |
N1—Sn1—Cl2 | 92.91 (5) | C8—C9—C10 | 121.2 (2) |
Cl3—Sn1—Cl2 | 92.68 (2) | C8—C9—H9 | 119.4 |
O1—Sn1—Cl1 | 93.77 (5) | C10—C9—H9 | 119.4 |
N1—Sn1—Cl1 | 168.64 (5) | C9—C10—C19 | 118.7 (2) |
Cl3—Sn1—Cl1 | 93.58 (2) | C9—C10—C11 | 122.1 (2) |
Cl2—Sn1—Cl1 | 96.88 (2) | C19—C10—C11 | 119.2 (2) |
O1—Sn1—Cl4 | 87.18 (5) | C12—C11—C10 | 120.4 (2) |
N1—Sn1—Cl4 | 83.78 (6) | C12—C11—H11 | 119.8 |
Cl3—Sn1—Cl4 | 173.96 (2) | C10—C11—H11 | 119.8 |
Cl2—Sn1—Cl4 | 91.54 (2) | C11—C12—C13 | 122.0 (3) |
Cl1—Sn1—Cl4 | 90.20 (2) | C11—C12—H12 | 119.0 |
C1—O1—Sn1 | 118.61 (15) | C13—C12—H12 | 119.0 |
C17—O3—H3 | 112 (2) | C14—C13—C18 | 119.9 (2) |
C20—O4—H4 | 109.5 (19) | C14—C13—C12 | 120.6 (2) |
C6—N1—C2 | 119.2 (2) | C18—C13—C12 | 119.6 (2) |
C6—N1—Sn1 | 127.39 (16) | C15—C14—C13 | 120.5 (3) |
C2—N1—Sn1 | 113.00 (15) | C15—C14—H14 | 119.8 |
C7—N2—C19 | 124.3 (2) | C13—C14—H14 | 119.8 |
C7—N2—H2 | 120 (2) | C14—C15—C16 | 120.8 (3) |
C19—N2—H2 | 115 (2) | C14—C15—H15 | 119.6 |
O2—C1—O1 | 124.9 (2) | C16—C15—H15 | 119.6 |
O2—C1—C2 | 119.1 (2) | C17—C16—C15 | 120.1 (2) |
O1—C1—C2 | 116.1 (2) | C17—C16—H16 | 119.9 |
N1—C2—C3 | 122.0 (2) | C15—C16—H16 | 119.9 |
N1—C2—C1 | 115.6 (2) | O3—C17—C16 | 122.6 (2) |
C3—C2—C1 | 122.4 (2) | O3—C17—C18 | 117.0 (2) |
C2—C3—C4 | 118.7 (2) | C16—C17—C18 | 120.4 (2) |
C2—C3—H3A | 120.7 | C17—C18—C13 | 118.4 (2) |
C4—C3—H3A | 120.7 | C17—C18—C19 | 124.0 (2) |
C5—C4—C3 | 119.2 (2) | C13—C18—C19 | 117.7 (2) |
C5—C4—H4A | 120.4 | N2—C19—C10 | 117.1 (2) |
C3—C4—H4A | 120.4 | N2—C19—C18 | 121.7 (2) |
C6—C5—C4 | 119.3 (2) | C10—C19—C18 | 121.1 (2) |
C6—C5—H5 | 120.4 | O4—C20—H20A | 109.5 |
C4—C5—H5 | 120.4 | O4—C20—H20B | 109.5 |
N1—C6—C5 | 121.6 (2) | H20A—C20—H20B | 109.5 |
N1—C6—H6 | 119.2 | O4—C20—H20C | 109.5 |
C5—C6—H6 | 119.2 | H20A—C20—H20C | 109.5 |
N2—C7—C8 | 120.1 (3) | H20B—C20—H20C | 109.5 |
N2—C7—H7 | 119.9 | ||
N1—Sn1—O1—C1 | −2.17 (18) | N2—C7—C8—C9 | −0.6 (4) |
Cl3—Sn1—O1—C1 | −94.42 (18) | C7—C8—C9—C10 | 0.1 (4) |
Cl2—Sn1—O1—C1 | −1.2 (4) | C8—C9—C10—C19 | 0.7 (4) |
Cl1—Sn1—O1—C1 | 172.13 (18) | C8—C9—C10—C11 | −178.4 (2) |
Cl4—Sn1—O1—C1 | 82.12 (18) | C9—C10—C11—C12 | 179.8 (2) |
O1—Sn1—N1—C6 | 177.6 (2) | C19—C10—C11—C12 | 0.7 (4) |
Cl3—Sn1—N1—C6 | −95.0 (2) | C10—C11—C12—C13 | 0.5 (4) |
Cl2—Sn1—N1—C6 | −2.2 (2) | C11—C12—C13—C14 | 179.7 (3) |
Cl1—Sn1—N1—C6 | 147.4 (2) | C11—C12—C13—C18 | −1.1 (4) |
Cl4—Sn1—N1—C6 | 89.0 (2) | C18—C13—C14—C15 | 0.2 (4) |
O1—Sn1—N1—C2 | 4.76 (17) | C12—C13—C14—C15 | 179.4 (3) |
Cl3—Sn1—N1—C2 | 92.16 (17) | C13—C14—C15—C16 | 0.1 (4) |
Cl2—Sn1—N1—C2 | −175.07 (17) | C14—C15—C16—C17 | 0.1 (4) |
Cl1—Sn1—N1—C2 | −25.5 (4) | C15—C16—C17—O3 | 178.8 (2) |
Cl4—Sn1—N1—C2 | −83.84 (17) | C15—C16—C17—C18 | −0.6 (4) |
Sn1—O1—C1—O2 | −179.9 (2) | O3—C17—C18—C13 | −178.5 (2) |
Sn1—O1—C1—C2 | −0.6 (3) | C16—C17—C18—C13 | 0.9 (4) |
C6—N1—C2—C3 | 0.0 (4) | O3—C17—C18—C19 | 1.1 (4) |
Sn1—N1—C2—C3 | 173.5 (2) | C16—C17—C18—C19 | −179.4 (2) |
C6—N1—C2—C1 | 180.0 (2) | C14—C13—C18—C17 | −0.7 (4) |
Sn1—N1—C2—C1 | −6.5 (3) | C12—C13—C18—C17 | −179.9 (2) |
O2—C1—C2—N1 | −175.7 (2) | C14—C13—C18—C19 | 179.6 (2) |
O1—C1—C2—N1 | 4.9 (3) | C12—C13—C18—C19 | 0.4 (4) |
O2—C1—C2—C3 | 4.3 (4) | C7—N2—C19—C10 | 0.5 (4) |
O1—C1—C2—C3 | −175.1 (3) | C7—N2—C19—C18 | −179.9 (2) |
N1—C2—C3—C4 | 0.0 (4) | C9—C10—C19—N2 | −1.0 (3) |
C1—C2—C3—C4 | −180.0 (2) | C11—C10—C19—N2 | 178.1 (2) |
C2—C3—C4—C5 | 0.4 (4) | C9—C10—C19—C18 | 179.5 (2) |
C3—C4—C5—C6 | −0.7 (4) | C11—C10—C19—C18 | −1.4 (4) |
C2—N1—C6—C5 | −0.4 (4) | C17—C18—C19—N2 | 1.7 (4) |
Sn1—N1—C6—C5 | −172.9 (2) | C13—C18—C19—N2 | −178.7 (2) |
C4—C5—C6—N1 | 0.8 (5) | C17—C18—C19—C10 | −178.8 (2) |
C19—N2—C7—C8 | 0.3 (4) | C13—C18—C19—C10 | 0.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.84 (1) | 1.73 (1) | 2.554 (2) | 170 (3) |
O4—H4···O2 | 0.83 (1) | 1.87 (1) | 2.698 (3) | 174 (3) |
N2—H2···Cl4i | 0.87 (1) | 2.58 (2) | 3.255 (2) | 135 (2) |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | (C13H10NO)[SnCl4(C6H4NO2)]·CH4O |
Mr | 610.85 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 100 |
a, b, c (Å) | 31.5065 (11), 8.0802 (2), 20.0948 (9) |
β (°) | 115.722 (5) |
V (Å3) | 4608.8 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.60 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.645, 0.856 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15316, 5326, 4445 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.065, 1.02 |
No. of reflections | 5326 |
No. of parameters | 293 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −0.44 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.84 (1) | 1.73 (1) | 2.554 (2) | 170 (3) |
O4—H4···O2 | 0.83 (1) | 1.87 (1) | 2.698 (3) | 174 (3) |
N2—H2···Cl4i | 0.87 (1) | 2.58 (2) | 3.255 (2) | 135 (2) |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
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
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, 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, m744. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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A previous study reported 4-(dimethylamino)pyridinium tetrachlorido(pyridine-2-carboxylato)stannate, which was synthesized by the reaction of 4-(dimethylamino)pyridine, picolinic acid and stannic chloride in methanol (Najafi et al., 2012). The reaction with 10-hydroxybenzo[h]quinoline in place of 4-(dimethylamino)pyridine yielded the analogous salt, (C13H10NO)[SnCl4(C6H4NO2)] as a methanol monosolvate (Scheme I). The SnIV atom is N,O-chelated by the picolinate ion in a cis-SnNOCl4 octahedral geometry. The cation is linked to the methanol molecule by an O–H···O hydrogen bond; the solvent molecule itself is hydrogen-bond donor to the double-bond carboxyl O atom of the anion (Table 1).