metal-organic compounds
Dimethylbis(2-methylquinolin-8-olato-κ2N,O)tin(IV)
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 SnIV cation in the title compound, [Sn(CH3)2(C10H8NO)2], is N,O-chelated by two 2-methylquinolin-8-olate anions and coordinated by two methyl groups in a skew-trapezoidal bipyramidal geometry. In the molecule, the two quinoline ring systems are twisted to one another at 10.91 (18)°. The dimethyltin skeleton [C—Sn—C = 149.6 (2)°] is bent over the longer edge of the trapezoid that is defined by the four chelating atoms. Weak intermolecular C—H⋯O hydrogen bonding occurs in the crystal.
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/S1600536812047393/xu5653sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047393/xu5653Isup2.hkl
Dimethyltin dichloride (0.22 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.36 g, 2 mmol) were loaded into a convection tube; the tube was filled with ethyl alcohol 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 0.93 to 0.96 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the
in the riding model approximation.As the atoms C15 to C19 showed somewhat elongated ellipsoids, their anisotropic temperature factors were restrained to approximate isotropic behavior.
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 (CH3)2Sn(C10H8NO)2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
[Sn(CH3)2(C10H8NO)2] | F(000) = 936 |
Mr = 465.11 | Dx = 1.552 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4858 reflections |
a = 8.0434 (4) Å | θ = 2.9–27.5° |
b = 20.6952 (10) Å | µ = 1.30 mm−1 |
c = 12.0102 (6) Å | T = 295 K |
β = 95.420 (5)° | Prism, yellow |
V = 1990.28 (17) Å3 | 0.25 × 0.25 × 0.05 mm |
Z = 4 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 4600 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3410 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.046 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.9° |
ω scan | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −26→26 |
Tmin = 0.737, Tmax = 0.938 | l = −11→15 |
20963 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0354P)2 + 1.6968P] where P = (Fo2 + 2Fc2)/3 |
4600 reflections | (Δ/σ)max = 0.001 |
246 parameters | Δρmax = 0.79 e Å−3 |
30 restraints | Δρmin = −0.49 e Å−3 |
[Sn(CH3)2(C10H8NO)2] | V = 1990.28 (17) Å3 |
Mr = 465.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.0434 (4) Å | µ = 1.30 mm−1 |
b = 20.6952 (10) Å | T = 295 K |
c = 12.0102 (6) Å | 0.25 × 0.25 × 0.05 mm |
β = 95.420 (5)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 4600 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 3410 reflections with I > 2σ(I) |
Tmin = 0.737, Tmax = 0.938 | Rint = 0.046 |
20963 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 30 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.79 e Å−3 |
4600 reflections | Δρmin = −0.49 e Å−3 |
246 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.31642 (3) | 0.682497 (12) | 0.39615 (2) | 0.04048 (10) | |
O1 | 0.4151 (3) | 0.60834 (13) | 0.3067 (3) | 0.0537 (7) | |
O2 | 0.5350 (3) | 0.72786 (13) | 0.3645 (2) | 0.0511 (7) | |
N1 | 0.1010 (4) | 0.59118 (17) | 0.3762 (3) | 0.0524 (9) | |
N2 | 0.3308 (6) | 0.79119 (19) | 0.4985 (3) | 0.0644 (11) | |
C1 | 0.1501 (6) | 0.7308 (2) | 0.2773 (4) | 0.0610 (12) | |
H1A | 0.1756 | 0.7195 | 0.2033 | 0.091* | |
H1B | 0.1618 | 0.7767 | 0.2876 | 0.091* | |
H1C | 0.0376 | 0.7183 | 0.2871 | 0.091* | |
C3 | −0.1319 (7) | 0.6398 (3) | 0.4603 (6) | 0.099 (2) | |
H3A | −0.0620 | 0.6773 | 0.4589 | 0.149* | |
H3B | −0.1453 | 0.6285 | 0.5365 | 0.149* | |
H3C | −0.2392 | 0.6489 | 0.4216 | 0.149* | |
C2 | 0.3722 (6) | 0.6462 (2) | 0.5594 (4) | 0.0641 (13) | |
H2A | 0.3911 | 0.6005 | 0.5561 | 0.096* | |
H2B | 0.2802 | 0.6546 | 0.6028 | 0.096* | |
H2C | 0.4707 | 0.6671 | 0.5937 | 0.096* | |
C4 | −0.0528 (6) | 0.5848 (3) | 0.4043 (4) | 0.0696 (15) | |
C5 | −0.1415 (7) | 0.5271 (4) | 0.3834 (5) | 0.085 (2) | |
H5 | −0.2499 | 0.5234 | 0.4037 | 0.102* | |
C6 | −0.0701 (9) | 0.4767 (3) | 0.3338 (5) | 0.093 (2) | |
H6 | −0.1293 | 0.4384 | 0.3215 | 0.112* | |
C7 | 0.0916 (7) | 0.4816 (2) | 0.3008 (4) | 0.0701 (16) | |
C8 | 0.1728 (11) | 0.4328 (3) | 0.2467 (5) | 0.095 (2) | |
H8 | 0.1207 | 0.3931 | 0.2323 | 0.114* | |
C9 | 0.3267 (11) | 0.4433 (3) | 0.2156 (5) | 0.098 (2) | |
H9 | 0.3788 | 0.4105 | 0.1790 | 0.117* | |
C10 | 0.4118 (7) | 0.5019 (2) | 0.2362 (4) | 0.0684 (14) | |
H10 | 0.5186 | 0.5072 | 0.2140 | 0.082* | |
C11 | 0.3376 (6) | 0.5519 (2) | 0.2895 (4) | 0.0511 (10) | |
C12 | 0.1746 (5) | 0.5415 (2) | 0.3235 (4) | 0.0510 (11) | |
C13 | 0.0724 (11) | 0.7858 (4) | 0.5910 (6) | 0.134 (3) | |
H13A | 0.0170 | 0.8107 | 0.6438 | 0.201* | |
H13B | 0.0992 | 0.7438 | 0.6218 | 0.201* | |
H13C | 0.0002 | 0.7811 | 0.5231 | 0.201* | |
C14 | 0.2287 (10) | 0.8192 (3) | 0.5665 (4) | 0.096 (2) | |
C15 | 0.2632 (14) | 0.8788 (4) | 0.6124 (6) | 0.125 (3) | |
H15 | 0.1897 | 0.8978 | 0.6580 | 0.150* | |
C16 | 0.3987 (12) | 0.9086 (3) | 0.5919 (6) | 0.106 (3) | |
H16 | 0.4212 | 0.9485 | 0.6255 | 0.127* | |
C17 | 0.5152 (11) | 0.8834 (3) | 0.5205 (6) | 0.100 (2) | |
C18 | 0.6547 (14) | 0.9089 (4) | 0.4912 (8) | 0.132 (3) | |
H18 | 0.6857 | 0.9488 | 0.5225 | 0.159* | |
C19 | 0.7582 (10) | 0.8829 (4) | 0.4195 (8) | 0.117 (3) | |
H19 | 0.8523 | 0.9053 | 0.4014 | 0.140* | |
C20 | 0.7173 (7) | 0.8171 (3) | 0.3703 (6) | 0.095 (2) | |
H20 | 0.7846 | 0.7974 | 0.3213 | 0.114* | |
C21 | 0.5752 (6) | 0.7875 (2) | 0.4016 (4) | 0.0576 (13) | |
C22 | 0.4726 (8) | 0.8203 (2) | 0.4745 (4) | 0.0658 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03944 (16) | 0.03883 (16) | 0.04375 (17) | 0.00020 (12) | 0.00699 (11) | 0.00239 (12) |
O1 | 0.0472 (16) | 0.0403 (16) | 0.076 (2) | −0.0065 (13) | 0.0160 (15) | −0.0110 (14) |
O2 | 0.0461 (16) | 0.0464 (17) | 0.0624 (18) | −0.0095 (13) | 0.0135 (14) | −0.0011 (14) |
N1 | 0.0410 (19) | 0.052 (2) | 0.063 (2) | −0.0057 (16) | −0.0012 (17) | 0.0181 (18) |
N2 | 0.099 (3) | 0.053 (2) | 0.039 (2) | 0.023 (2) | −0.006 (2) | −0.0055 (18) |
C1 | 0.060 (3) | 0.058 (3) | 0.062 (3) | 0.004 (2) | −0.005 (2) | 0.009 (2) |
C3 | 0.055 (3) | 0.110 (5) | 0.138 (6) | 0.022 (3) | 0.034 (4) | 0.050 (5) |
C2 | 0.067 (3) | 0.068 (3) | 0.056 (3) | −0.004 (2) | 0.002 (2) | 0.020 (2) |
C4 | 0.041 (2) | 0.089 (4) | 0.078 (3) | −0.010 (3) | −0.004 (2) | 0.037 (3) |
C5 | 0.053 (3) | 0.118 (5) | 0.079 (4) | −0.036 (3) | −0.013 (3) | 0.047 (4) |
C6 | 0.097 (5) | 0.103 (5) | 0.071 (4) | −0.065 (4) | −0.029 (4) | 0.038 (4) |
C7 | 0.093 (4) | 0.058 (3) | 0.053 (3) | −0.034 (3) | −0.021 (3) | 0.014 (2) |
C8 | 0.159 (7) | 0.053 (3) | 0.068 (4) | −0.040 (4) | −0.013 (4) | −0.005 (3) |
C9 | 0.162 (7) | 0.050 (3) | 0.078 (4) | −0.007 (4) | −0.001 (4) | −0.018 (3) |
C10 | 0.088 (4) | 0.047 (3) | 0.069 (3) | 0.002 (3) | 0.004 (3) | −0.010 (2) |
C11 | 0.062 (3) | 0.038 (2) | 0.052 (2) | −0.001 (2) | −0.002 (2) | −0.0003 (19) |
C12 | 0.055 (3) | 0.046 (2) | 0.049 (2) | −0.010 (2) | −0.010 (2) | 0.011 (2) |
C13 | 0.144 (7) | 0.190 (8) | 0.077 (4) | 0.086 (7) | 0.060 (5) | 0.019 (5) |
C14 | 0.160 (7) | 0.085 (4) | 0.040 (3) | 0.066 (4) | −0.009 (4) | −0.014 (3) |
C15 | 0.174 (7) | 0.116 (6) | 0.080 (4) | 0.063 (5) | −0.015 (5) | −0.021 (4) |
C16 | 0.172 (6) | 0.062 (4) | 0.072 (4) | 0.042 (4) | −0.045 (4) | −0.032 (3) |
C17 | 0.132 (5) | 0.067 (4) | 0.089 (4) | 0.000 (4) | −0.054 (4) | 0.010 (3) |
C18 | 0.149 (7) | 0.094 (5) | 0.139 (6) | −0.020 (5) | −0.067 (6) | 0.026 (5) |
C19 | 0.086 (4) | 0.097 (5) | 0.156 (6) | −0.053 (4) | −0.045 (4) | 0.062 (4) |
C20 | 0.057 (3) | 0.077 (4) | 0.143 (6) | −0.022 (3) | −0.025 (4) | 0.053 (4) |
C21 | 0.054 (3) | 0.049 (3) | 0.065 (3) | −0.013 (2) | −0.018 (2) | 0.023 (2) |
C22 | 0.100 (4) | 0.037 (2) | 0.053 (3) | 0.007 (3) | −0.033 (3) | −0.004 (2) |
Sn1—O2 | 2.060 (3) | C7—C8 | 1.397 (9) |
Sn1—O1 | 2.073 (3) | C7—C12 | 1.422 (6) |
Sn1—C2 | 2.108 (4) | C8—C9 | 1.344 (10) |
Sn1—C1 | 2.113 (4) | C8—H8 | 0.9300 |
Sn1—N1 | 2.560 (3) | C9—C10 | 1.403 (8) |
Sn1—N2 | 2.561 (4) | C9—H9 | 0.9300 |
O1—C11 | 1.331 (5) | C10—C11 | 1.381 (6) |
O2—C21 | 1.341 (5) | C10—H10 | 0.9300 |
N1—C4 | 1.320 (6) | C11—C12 | 1.426 (6) |
N1—C12 | 1.369 (6) | C13—C14 | 1.489 (11) |
N2—C14 | 1.343 (7) | C13—H13A | 0.9600 |
N2—C22 | 1.345 (7) | C13—H13B | 0.9600 |
C1—H1A | 0.9600 | C13—H13C | 0.9600 |
C1—H1B | 0.9600 | C14—C15 | 1.368 (10) |
C1—H1C | 0.9600 | C15—C16 | 1.296 (11) |
C3—C4 | 1.495 (8) | C15—H15 | 0.9300 |
C3—H3A | 0.9600 | C16—C17 | 1.427 (11) |
C3—H3B | 0.9600 | C16—H16 | 0.9300 |
C3—H3C | 0.9600 | C17—C18 | 1.318 (12) |
C2—H2A | 0.9600 | C17—C22 | 1.448 (7) |
C2—H2B | 0.9600 | C18—C19 | 1.364 (12) |
C2—H2C | 0.9600 | C18—H18 | 0.9300 |
C4—C5 | 1.400 (8) | C19—C20 | 1.508 (10) |
C5—C6 | 1.356 (9) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.380 (7) |
C6—C7 | 1.399 (9) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C21—C22 | 1.430 (8) |
O2—Sn1—O1 | 82.34 (11) | C8—C7—C12 | 119.3 (5) |
O2—Sn1—C2 | 102.92 (16) | C6—C7—C12 | 116.1 (6) |
O1—Sn1—C2 | 99.20 (17) | C9—C8—C7 | 119.6 (5) |
O2—Sn1—C1 | 99.00 (16) | C9—C8—H8 | 120.2 |
O1—Sn1—C1 | 104.44 (16) | C7—C8—H8 | 120.2 |
C2—Sn1—C1 | 149.6 (2) | C8—C9—C10 | 122.6 (6) |
O2—Sn1—N1 | 154.31 (12) | C8—C9—H9 | 118.7 |
O1—Sn1—N1 | 72.16 (12) | C10—C9—H9 | 118.7 |
C2—Sn1—N1 | 84.66 (15) | C11—C10—C9 | 120.3 (6) |
C1—Sn1—N1 | 84.63 (15) | C11—C10—H10 | 119.9 |
O2—Sn1—N2 | 71.80 (14) | C9—C10—H10 | 119.9 |
O1—Sn1—N2 | 153.73 (14) | O1—C11—C10 | 120.8 (4) |
C2—Sn1—N2 | 82.55 (16) | O1—C11—C12 | 121.2 (4) |
C1—Sn1—N2 | 84.58 (15) | C10—C11—C12 | 118.0 (4) |
N1—Sn1—N2 | 133.87 (15) | N1—C12—C7 | 121.8 (5) |
C11—O1—Sn1 | 122.2 (3) | N1—C12—C11 | 117.9 (4) |
C21—O2—Sn1 | 122.8 (3) | C7—C12—C11 | 120.2 (5) |
C4—N1—C12 | 120.0 (4) | C14—C13—H13A | 109.5 |
C4—N1—Sn1 | 133.9 (4) | C14—C13—H13B | 109.5 |
C12—N1—Sn1 | 106.2 (3) | H13A—C13—H13B | 109.5 |
C14—N2—C22 | 121.1 (5) | C14—C13—H13C | 109.5 |
C14—N2—Sn1 | 132.0 (5) | H13A—C13—H13C | 109.5 |
C22—N2—Sn1 | 106.9 (3) | H13B—C13—H13C | 109.5 |
Sn1—C1—H1A | 109.5 | N2—C14—C15 | 121.4 (9) |
Sn1—C1—H1B | 109.5 | N2—C14—C13 | 119.7 (6) |
H1A—C1—H1B | 109.5 | C15—C14—C13 | 118.8 (7) |
Sn1—C1—H1C | 109.5 | C16—C15—C14 | 119.6 (9) |
H1A—C1—H1C | 109.5 | C16—C15—H15 | 120.2 |
H1B—C1—H1C | 109.5 | C14—C15—H15 | 120.2 |
C4—C3—H3A | 109.5 | C15—C16—C17 | 123.5 (7) |
C4—C3—H3B | 109.5 | C15—C16—H16 | 118.2 |
H3A—C3—H3B | 109.5 | C17—C16—H16 | 118.2 |
C4—C3—H3C | 109.5 | C18—C17—C16 | 129.7 (8) |
H3A—C3—H3C | 109.5 | C18—C17—C22 | 115.9 (9) |
H3B—C3—H3C | 109.5 | C16—C17—C22 | 114.5 (7) |
Sn1—C2—H2A | 109.5 | C17—C18—C19 | 126.6 (9) |
Sn1—C2—H2B | 109.5 | C17—C18—H18 | 116.7 |
H2A—C2—H2B | 109.5 | C19—C18—H18 | 116.7 |
Sn1—C2—H2C | 109.5 | C18—C19—C20 | 118.7 (7) |
H2A—C2—H2C | 109.5 | C18—C19—H19 | 120.6 |
H2B—C2—H2C | 109.5 | C20—C19—H19 | 120.6 |
N1—C4—C5 | 120.9 (6) | C21—C20—C19 | 116.7 (7) |
N1—C4—C3 | 119.2 (5) | C21—C20—H20 | 121.6 |
C5—C4—C3 | 119.9 (5) | C19—C20—H20 | 121.6 |
C6—C5—C4 | 120.3 (6) | O2—C21—C20 | 119.9 (5) |
C6—C5—H5 | 119.9 | O2—C21—C22 | 120.3 (4) |
C4—C5—H5 | 119.9 | C20—C21—C22 | 119.8 (5) |
C5—C6—C7 | 120.9 (5) | N2—C22—C21 | 118.0 (4) |
C5—C6—H6 | 119.6 | N2—C22—C17 | 119.8 (6) |
C7—C6—H6 | 119.6 | C21—C22—C17 | 122.2 (6) |
C8—C7—C6 | 124.6 (6) | ||
O2—Sn1—O1—C11 | 178.2 (3) | Sn1—O1—C11—C12 | 5.6 (5) |
C2—Sn1—O1—C11 | 76.3 (3) | C9—C10—C11—O1 | −178.1 (5) |
C1—Sn1—O1—C11 | −84.4 (3) | C9—C10—C11—C12 | 0.8 (7) |
N1—Sn1—O1—C11 | −5.0 (3) | C4—N1—C12—C7 | −2.0 (6) |
N2—Sn1—O1—C11 | 168.1 (3) | Sn1—N1—C12—C7 | 178.5 (3) |
O1—Sn1—O2—C21 | −178.9 (3) | C4—N1—C12—C11 | 176.8 (4) |
C2—Sn1—O2—C21 | −81.2 (3) | Sn1—N1—C12—C11 | −2.8 (4) |
C1—Sn1—O2—C21 | 77.6 (3) | C8—C7—C12—N1 | 179.9 (4) |
N1—Sn1—O2—C21 | 174.0 (3) | C6—C7—C12—N1 | 0.9 (6) |
N2—Sn1—O2—C21 | −3.6 (3) | C8—C7—C12—C11 | 1.2 (7) |
O2—Sn1—N1—C4 | −168.1 (4) | C6—C7—C12—C11 | −177.8 (4) |
O1—Sn1—N1—C4 | −175.5 (4) | O1—C11—C12—N1 | −1.0 (6) |
C2—Sn1—N1—C4 | 83.0 (4) | C10—C11—C12—N1 | −179.9 (4) |
C1—Sn1—N1—C4 | −68.5 (4) | O1—C11—C12—C7 | 177.8 (4) |
N2—Sn1—N1—C4 | 8.7 (5) | C10—C11—C12—C7 | −1.1 (6) |
O2—Sn1—N1—C12 | 11.4 (4) | C22—N2—C14—C15 | 1.2 (8) |
O1—Sn1—N1—C12 | 4.0 (2) | Sn1—N2—C14—C15 | 179.9 (4) |
C2—Sn1—N1—C12 | −97.5 (3) | C22—N2—C14—C13 | 179.8 (5) |
C1—Sn1—N1—C12 | 111.0 (3) | Sn1—N2—C14—C13 | −1.5 (7) |
N2—Sn1—N1—C12 | −171.8 (2) | N2—C14—C15—C16 | −1.4 (10) |
O2—Sn1—N2—C14 | −177.6 (4) | C13—C14—C15—C16 | −180.0 (7) |
O1—Sn1—N2—C14 | −167.0 (4) | C14—C15—C16—C17 | 1.7 (12) |
C2—Sn1—N2—C14 | −71.3 (4) | C15—C16—C17—C18 | 178.6 (8) |
C1—Sn1—N2—C14 | 81.1 (4) | C15—C16—C17—C22 | −1.7 (9) |
N1—Sn1—N2—C14 | 3.9 (5) | C16—C17—C18—C19 | −177.9 (7) |
O2—Sn1—N2—C22 | 1.3 (3) | C22—C17—C18—C19 | 2.4 (11) |
O1—Sn1—N2—C22 | 11.9 (4) | C17—C18—C19—C20 | −2.6 (12) |
C2—Sn1—N2—C22 | 107.6 (3) | C18—C19—C20—C21 | 0.2 (9) |
C1—Sn1—N2—C22 | −100.0 (3) | Sn1—O2—C21—C20 | −175.0 (3) |
N1—Sn1—N2—C22 | −177.2 (2) | Sn1—O2—C21—C22 | 5.7 (5) |
C12—N1—C4—C5 | 1.4 (7) | C19—C20—C21—O2 | −177.4 (4) |
Sn1—N1—C4—C5 | −179.1 (3) | C19—C20—C21—C22 | 1.9 (7) |
C12—N1—C4—C3 | −179.2 (4) | C14—N2—C22—C21 | 179.9 (4) |
Sn1—N1—C4—C3 | 0.3 (7) | Sn1—N2—C22—C21 | 0.9 (4) |
N1—C4—C5—C6 | 0.1 (8) | C14—N2—C22—C17 | −1.2 (7) |
C3—C4—C5—C6 | −179.3 (5) | Sn1—N2—C22—C17 | 179.7 (3) |
C4—C5—C6—C7 | −1.2 (8) | O2—C21—C22—N2 | −4.0 (6) |
C5—C6—C7—C8 | −178.3 (5) | C20—C21—C22—N2 | 176.7 (4) |
C5—C6—C7—C12 | 0.6 (7) | O2—C21—C22—C17 | 177.2 (4) |
C6—C7—C8—C9 | 178.0 (6) | C20—C21—C22—C17 | −2.1 (7) |
C12—C7—C8—C9 | −0.9 (8) | C18—C17—C22—N2 | −178.8 (5) |
C7—C8—C9—C10 | 0.7 (10) | C16—C17—C22—N2 | 1.4 (7) |
C8—C9—C10—C11 | −0.6 (9) | C18—C17—C22—C21 | 0.0 (8) |
Sn1—O1—C11—C10 | −175.5 (3) | C16—C17—C22—C21 | −179.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3C···O2i | 0.96 | 2.49 | 3.353 (7) | 149 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)2(C10H8NO)2] |
Mr | 465.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 8.0434 (4), 20.6952 (10), 12.0102 (6) |
β (°) | 95.420 (5) |
V (Å3) | 1990.28 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.30 |
Crystal size (mm) | 0.25 × 0.25 × 0.05 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.737, 0.938 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20963, 4600, 3410 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.094, 1.05 |
No. of reflections | 4600 |
No. of parameters | 246 |
No. of restraints | 30 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.49 |
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 |
C3—H3C···O2i | 0.96 | 2.49 | 3.353 (7) | 149 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
The authors 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
Das, V. G., Chen, W., Yap, C. K. & Sinn, E. (1984). Chem. Commun. pp. 1418–1419. CrossRef 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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The deprotonated 2-methy-8-hydroxyquinoline ligand chelates to the metal atom of a diorganotin skeleton bu the proximity of the methyl substitutent in the aromatic system results in a six-coordinate geometry that is distorted towards a skew-trapezoidal bipyramid, as noted in the ethylpropyltin derivative (Kumar Das et al., 1984). The SnIV atom in the dimethyltin analog (Scheme I, Fig. 1) is chelated by the 2-methyl-8-quinolinate ion and it exists in a skew-trapezoidal bipyramidal geometry [C–Sn–C 149.6 (2) °].
The dimethyltin skeleton is arched over the long side of the trazepoid defined by the chelating N and O atoms.