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metal-organic compounds
Monoclinic modification of di-n-butyldichlorido(1,10-phenanthroline-κ2N,N′)tin(IV)
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The Sn(IV) atom in the title compound, [Sn(C4H9)2Cl2(C12H8N2)], is chelated by the N-heterocycle; the n-butyl groups are trans to each other whereas the Cl atoms are cis to each other. The crystal studied was a non-merohedral twin with the minor domain being in a 15.8 (1)% proportion.
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent Technologies, 2010); 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
https://doi.org/10.1107/S1600536810048300/hg2755sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048300/hg2755Isup2.hkl
Di-n-butyltin dichloride (0.15 g, 0.5 mmol) and 1,10-phenanthroline hydrate (0.10, 0.5 mmol) were dissolved in boiling ethanol (10 mol). Colorless plates separated from solution after several days. A tiny platelet was prized from a lump of larger blocked that grew on top of each other.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The anisotropic temperature factors of the C9 atom were restrained to be nearly isotropic so as to prevent the atom from being too oblate.The final difference Fourier map had a peak and a hole in the vicinity of Cl2.
The crystal studied is a non-merohedral twin; the minor component refined to a 15.8 (1)% proportion.
The di-n-butyltin dichloride adduct with 1,10-phenanthroline (Scheme I) belongs to the P212121
(Ganis et al., 1983). The complexation of the organotin halide with the N-heterocycle in ethanol solvent yielded a monoclinic modification as plate-like crystals that grew over one another. The molecule has the tin atom in an octahedral geometry (Fig. 1). The n-butyl groups are trans to each other whereas the chlorine atoms are cis to each other. The crystal studied is a non-merohedral twin with the minor domain being in a 15.8 (1)% proportion; the nature of the twin led to a moderately satisfactory weighting scheme in the refinement.For the orthorhombic modification, see: Ganis et al. (1983).
Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell
CrysAlis PRO (Agilent Technologies, 2010); data reduction: CrysAlis PRO (Agilent Technologies, 2010); 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 SnCl2(C4H9)2(C12H8N2)2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
[Sn(C4H9)2Cl2(C12H8N2)] | F(000) = 976 |
Mr = 484.02 | Dx = 1.540 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 13483 reflections |
a = 11.1400 (2) Å | θ = 4.0–74.1° |
b = 10.4566 (2) Å | µ = 12.12 mm−1 |
c = 17.9375 (4) Å | T = 100 K |
β = 92.125 (2)° | Plate, colorless |
V = 2088.04 (7) Å3 | 0.20 × 0.10 × 0.02 mm |
Z = 4 |
Agilent SuperNova diffractometer | 11290 independent reflections |
Radiation source: fine-focus sealed tube | 10561 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 74.2°, θmin = 4.0° |
ω scans | h = −13→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010) | k = −13→13 |
Tmin = 0.196, Tmax = 0.794 | l = −22→22 |
15170 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1271P)2 + 6.6598P] where P = (Fo2 + 2Fc2)/3 |
11290 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 2.11 e Å−3 |
6 restraints | Δρmin = −1.95 e Å−3 |
[Sn(C4H9)2Cl2(C12H8N2)] | V = 2088.04 (7) Å3 |
Mr = 484.02 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 11.1400 (2) Å | µ = 12.12 mm−1 |
b = 10.4566 (2) Å | T = 100 K |
c = 17.9375 (4) Å | 0.20 × 0.10 × 0.02 mm |
β = 92.125 (2)° |
Agilent SuperNova diffractometer | 11290 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010) | 10561 reflections with I > 2σ(I) |
Tmin = 0.196, Tmax = 0.794 | Rint = 0.046 |
15170 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 6 restraints |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.08 | Δρmax = 2.11 e Å−3 |
11290 reflections | Δρmin = −1.95 e Å−3 |
227 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.850086 (19) | 0.57324 (2) | 0.236808 (12) | 0.00995 (12) | |
Cl1 | 0.77760 (8) | 0.43243 (8) | 0.12497 (5) | 0.0141 (2) | |
Cl2 | 1.07589 (8) | 0.55970 (9) | 0.24257 (5) | 0.0181 (2) | |
N1 | 0.6455 (3) | 0.6191 (3) | 0.26722 (16) | 0.0131 (7) | |
N2 | 0.8463 (3) | 0.7174 (3) | 0.33789 (17) | 0.0132 (6) | |
C1 | 0.8297 (4) | 0.4069 (4) | 0.3057 (2) | 0.0167 (8) | |
H1A | 0.7486 | 0.3711 | 0.2953 | 0.020* | |
H1B | 0.8886 | 0.3419 | 0.2906 | 0.020* | |
C2 | 0.8459 (4) | 0.4277 (4) | 0.3895 (2) | 0.0204 (9) | |
H2A | 0.7851 | 0.4899 | 0.4056 | 0.024* | |
H2B | 0.9262 | 0.4650 | 0.4005 | 0.024* | |
C3 | 0.8336 (5) | 0.3035 (5) | 0.4346 (3) | 0.0290 (10) | |
H3A | 0.8984 | 0.2441 | 0.4210 | 0.035* | |
H3B | 0.8455 | 0.3238 | 0.4883 | 0.035* | |
C4 | 0.7140 (5) | 0.2362 (5) | 0.4229 (3) | 0.0308 (11) | |
H4A | 0.7134 | 0.1582 | 0.4531 | 0.046* | |
H4B | 0.7020 | 0.2138 | 0.3701 | 0.046* | |
H4C | 0.6492 | 0.2931 | 0.4378 | 0.046* | |
C5 | 0.8563 (4) | 0.7339 (4) | 0.1626 (2) | 0.0147 (7) | |
H5A | 0.9006 | 0.8037 | 0.1889 | 0.018* | |
H5B | 0.9039 | 0.7088 | 0.1194 | 0.018* | |
C6 | 0.7366 (4) | 0.7876 (4) | 0.1328 (2) | 0.0170 (8) | |
H6A | 0.6883 | 0.8148 | 0.1752 | 0.020* | |
H6B | 0.6916 | 0.7196 | 0.1054 | 0.020* | |
C7 | 0.7538 (4) | 0.9014 (4) | 0.0808 (2) | 0.0193 (8) | |
H7A | 0.8073 | 0.8760 | 0.0405 | 0.023* | |
H7B | 0.7933 | 0.9719 | 0.1092 | 0.023* | |
C8 | 0.6344 (4) | 0.9490 (4) | 0.0463 (2) | 0.0232 (9) | |
H8A | 0.6493 | 1.0215 | 0.0132 | 0.035* | |
H8B | 0.5819 | 0.9762 | 0.0859 | 0.035* | |
H8C | 0.5956 | 0.8799 | 0.0175 | 0.035* | |
C9 | 0.5485 (3) | 0.5678 (4) | 0.2335 (2) | 0.0143 (8) | |
H9 | 0.5588 | 0.5109 | 0.1929 | 0.017* | |
C10 | 0.4306 (3) | 0.5949 (4) | 0.2560 (2) | 0.0165 (8) | |
H10 | 0.3630 | 0.5561 | 0.2313 | 0.020* | |
C11 | 0.4158 (4) | 0.6779 (4) | 0.3140 (2) | 0.0185 (8) | |
H11 | 0.3373 | 0.6981 | 0.3293 | 0.022* | |
C12 | 0.5168 (4) | 0.7337 (4) | 0.3512 (2) | 0.0146 (8) | |
C13 | 0.6310 (3) | 0.7008 (4) | 0.3260 (2) | 0.0129 (7) | |
C14 | 0.5086 (4) | 0.8193 (4) | 0.4132 (2) | 0.0178 (8) | |
H14 | 0.4318 | 0.8409 | 0.4309 | 0.021* | |
C15 | 0.6084 (4) | 0.8701 (4) | 0.4470 (2) | 0.0176 (8) | |
H15 | 0.6006 | 0.9274 | 0.4877 | 0.021* | |
C16 | 0.7249 (4) | 0.8387 (4) | 0.4224 (2) | 0.0144 (8) | |
C17 | 0.7368 (4) | 0.7535 (4) | 0.3623 (2) | 0.0127 (7) | |
C18 | 0.8308 (4) | 0.8872 (4) | 0.4573 (2) | 0.0163 (8) | |
H18 | 0.8265 | 0.9445 | 0.4982 | 0.020* | |
C19 | 0.9403 (4) | 0.8510 (4) | 0.4316 (2) | 0.0178 (8) | |
H19 | 1.0126 | 0.8832 | 0.4543 | 0.021* | |
C20 | 0.9440 (4) | 0.7658 (4) | 0.3714 (2) | 0.0154 (8) | |
H20 | 1.0201 | 0.7416 | 0.3538 | 0.018* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01113 (16) | 0.00941 (16) | 0.00932 (16) | 0.00028 (9) | 0.00064 (10) | 0.00029 (7) |
Cl1 | 0.0165 (4) | 0.0137 (5) | 0.0122 (4) | −0.0033 (3) | 0.0011 (3) | −0.0012 (3) |
Cl2 | 0.0148 (4) | 0.0177 (5) | 0.0218 (5) | 0.0010 (4) | 0.0015 (4) | 0.0016 (3) |
N1 | 0.0161 (18) | 0.0099 (16) | 0.0135 (15) | −0.0038 (12) | 0.0006 (13) | −0.0013 (11) |
N2 | 0.0169 (17) | 0.0113 (15) | 0.0113 (14) | 0.0026 (13) | 0.0013 (12) | −0.0023 (11) |
C1 | 0.023 (2) | 0.0127 (17) | 0.0148 (18) | 0.0005 (16) | 0.0005 (15) | 0.0012 (14) |
C2 | 0.026 (2) | 0.021 (2) | 0.0139 (19) | −0.0023 (17) | 0.0005 (16) | 0.0048 (14) |
C3 | 0.035 (3) | 0.031 (3) | 0.021 (2) | 0.011 (2) | 0.0071 (19) | 0.0113 (18) |
C4 | 0.050 (3) | 0.017 (2) | 0.025 (2) | −0.001 (2) | 0.010 (2) | 0.0013 (17) |
C5 | 0.0162 (18) | 0.0140 (18) | 0.0138 (16) | −0.0022 (15) | 0.0006 (14) | 0.0018 (13) |
C6 | 0.0164 (19) | 0.0157 (19) | 0.0189 (18) | 0.0007 (16) | −0.0001 (15) | 0.0024 (15) |
C7 | 0.024 (2) | 0.0156 (18) | 0.0183 (18) | −0.0009 (17) | −0.0046 (16) | 0.0022 (16) |
C8 | 0.029 (2) | 0.019 (2) | 0.022 (2) | 0.0066 (18) | −0.0054 (17) | 0.0017 (16) |
C9 | 0.0026 (16) | 0.018 (2) | 0.0218 (19) | −0.0003 (14) | −0.0025 (14) | 0.0012 (14) |
C10 | 0.0059 (18) | 0.0191 (19) | 0.024 (2) | 0.0057 (15) | −0.0003 (14) | 0.0005 (15) |
C11 | 0.0122 (18) | 0.022 (2) | 0.0215 (18) | 0.0017 (16) | −0.0012 (15) | 0.0043 (16) |
C12 | 0.0131 (19) | 0.0135 (18) | 0.0171 (17) | 0.0030 (15) | 0.0006 (14) | 0.0031 (14) |
C13 | 0.0123 (19) | 0.0141 (18) | 0.0121 (16) | 0.0076 (15) | 0.0005 (14) | 0.0030 (13) |
C14 | 0.0169 (19) | 0.020 (2) | 0.0160 (17) | 0.0069 (16) | 0.0030 (14) | 0.0007 (15) |
C15 | 0.021 (2) | 0.018 (2) | 0.0141 (17) | 0.0063 (16) | 0.0021 (15) | −0.0023 (14) |
C16 | 0.019 (2) | 0.0119 (19) | 0.0125 (16) | 0.0018 (15) | 0.0023 (14) | 0.0024 (14) |
C17 | 0.0144 (19) | 0.0112 (18) | 0.0122 (16) | 0.0006 (14) | −0.0025 (13) | 0.0042 (14) |
C18 | 0.023 (2) | 0.0127 (19) | 0.0136 (16) | −0.0016 (16) | 0.0001 (15) | −0.0011 (14) |
C19 | 0.019 (2) | 0.020 (2) | 0.0144 (17) | −0.0057 (17) | −0.0001 (15) | −0.0028 (15) |
C20 | 0.0112 (18) | 0.017 (2) | 0.0173 (17) | −0.0018 (15) | −0.0008 (14) | −0.0009 (15) |
Sn1—C5 | 2.146 (4) | C6—H6B | 0.9900 |
Sn1—C1 | 2.150 (4) | C7—C8 | 1.530 (6) |
Sn1—N2 | 2.360 (3) | C7—H7A | 0.9900 |
Sn1—N1 | 2.412 (3) | C7—H7B | 0.9900 |
Sn1—Cl2 | 2.5177 (9) | C8—H8A | 0.9800 |
Sn1—Cl1 | 2.5931 (9) | C8—H8B | 0.9800 |
N1—C9 | 1.331 (5) | C8—H8C | 0.9800 |
N1—C13 | 1.371 (5) | C9—C10 | 1.417 (5) |
N2—C20 | 1.323 (5) | C9—H9 | 0.9500 |
N2—C17 | 1.365 (5) | C10—C11 | 1.371 (6) |
C1—C2 | 1.523 (6) | C10—H10 | 0.9500 |
C1—H1A | 0.9900 | C11—C12 | 1.413 (6) |
C1—H1B | 0.9900 | C11—H11 | 0.9500 |
C2—C3 | 1.538 (6) | C12—C13 | 1.408 (5) |
C2—H2A | 0.9900 | C12—C14 | 1.434 (6) |
C2—H2B | 0.9900 | C13—C17 | 1.435 (5) |
C3—C4 | 1.515 (7) | C14—C15 | 1.355 (6) |
C3—H3A | 0.9900 | C14—H14 | 0.9500 |
C3—H3B | 0.9900 | C15—C16 | 1.424 (5) |
C4—H4A | 0.9800 | C15—H15 | 0.9500 |
C4—H4B | 0.9800 | C16—C17 | 1.409 (5) |
C4—H4C | 0.9800 | C16—C18 | 1.409 (6) |
C5—C6 | 1.525 (5) | C18—C19 | 1.373 (6) |
C5—H5A | 0.9900 | C18—H18 | 0.9500 |
C5—H5B | 0.9900 | C19—C20 | 1.402 (5) |
C6—C7 | 1.528 (6) | C19—H19 | 0.9500 |
C6—H6A | 0.9900 | C20—H20 | 0.9500 |
C5—Sn1—C1 | 174.93 (15) | C7—C6—H6A | 109.2 |
C5—Sn1—N2 | 88.76 (13) | C5—C6—H6B | 109.2 |
C1—Sn1—N2 | 94.01 (13) | C7—C6—H6B | 109.2 |
C5—Sn1—N1 | 92.13 (13) | H6A—C6—H6B | 107.9 |
C1—Sn1—N1 | 84.85 (14) | C6—C7—C8 | 112.0 (4) |
N2—Sn1—N1 | 69.83 (11) | C6—C7—H7A | 109.2 |
C5—Sn1—Cl2 | 90.81 (11) | C8—C7—H7A | 109.2 |
C1—Sn1—Cl2 | 93.29 (12) | C6—C7—H7B | 109.2 |
N2—Sn1—Cl2 | 92.90 (9) | C8—C7—H7B | 109.2 |
N1—Sn1—Cl2 | 162.40 (8) | H7A—C7—H7B | 107.9 |
C5—Sn1—Cl1 | 88.91 (10) | C7—C8—H8A | 109.5 |
C1—Sn1—Cl1 | 87.07 (11) | C7—C8—H8B | 109.5 |
N2—Sn1—Cl1 | 160.62 (9) | H8A—C8—H8B | 109.5 |
N1—Sn1—Cl1 | 91.04 (8) | C7—C8—H8C | 109.5 |
Cl2—Sn1—Cl1 | 106.37 (3) | H8A—C8—H8C | 109.5 |
C9—N1—C13 | 118.9 (3) | H8B—C8—H8C | 109.5 |
C9—N1—Sn1 | 125.1 (3) | N1—C9—C10 | 122.4 (4) |
C13—N1—Sn1 | 115.9 (2) | N1—C9—H9 | 118.8 |
C20—N2—C17 | 118.6 (3) | C10—C9—H9 | 118.8 |
C20—N2—Sn1 | 123.7 (3) | C11—C10—C9 | 118.8 (4) |
C17—N2—Sn1 | 117.7 (3) | C11—C10—H10 | 120.6 |
C2—C1—Sn1 | 116.2 (3) | C9—C10—H10 | 120.6 |
C2—C1—H1A | 108.2 | C10—C11—C12 | 120.3 (4) |
Sn1—C1—H1A | 108.2 | C10—C11—H11 | 119.9 |
C2—C1—H1B | 108.2 | C12—C11—H11 | 119.9 |
Sn1—C1—H1B | 108.2 | C13—C12—C11 | 117.5 (4) |
H1A—C1—H1B | 107.4 | C13—C12—C14 | 119.1 (4) |
C1—C2—C3 | 112.9 (4) | C11—C12—C14 | 123.4 (4) |
C1—C2—H2A | 109.0 | N1—C13—C12 | 122.2 (4) |
C3—C2—H2A | 109.0 | N1—C13—C17 | 118.0 (3) |
C1—C2—H2B | 109.0 | C12—C13—C17 | 119.8 (4) |
C3—C2—H2B | 109.0 | C15—C14—C12 | 121.1 (4) |
H2A—C2—H2B | 107.8 | C15—C14—H14 | 119.4 |
C4—C3—C2 | 114.4 (4) | C12—C14—H14 | 119.4 |
C4—C3—H3A | 108.6 | C14—C15—C16 | 120.9 (4) |
C2—C3—H3A | 108.6 | C14—C15—H15 | 119.6 |
C4—C3—H3B | 108.6 | C16—C15—H15 | 119.6 |
C2—C3—H3B | 108.6 | C17—C16—C18 | 117.8 (4) |
H3A—C3—H3B | 107.6 | C17—C16—C15 | 119.7 (4) |
C3—C4—H4A | 109.5 | C18—C16—C15 | 122.5 (4) |
C3—C4—H4B | 109.5 | N2—C17—C16 | 122.1 (4) |
H4A—C4—H4B | 109.5 | N2—C17—C13 | 118.5 (4) |
C3—C4—H4C | 109.5 | C16—C17—C13 | 119.4 (4) |
H4A—C4—H4C | 109.5 | C19—C18—C16 | 119.4 (4) |
H4B—C4—H4C | 109.5 | C19—C18—H18 | 120.3 |
C6—C5—Sn1 | 117.2 (3) | C16—C18—H18 | 120.3 |
C6—C5—H5A | 108.0 | C18—C19—C20 | 119.0 (4) |
Sn1—C5—H5A | 108.0 | C18—C19—H19 | 120.5 |
C6—C5—H5B | 108.0 | C20—C19—H19 | 120.5 |
Sn1—C5—H5B | 108.0 | N2—C20—C19 | 123.1 (4) |
H5A—C5—H5B | 107.2 | N2—C20—H20 | 118.5 |
C5—C6—C7 | 111.9 (3) | C19—C20—H20 | 118.5 |
C5—C6—H6A | 109.2 | ||
C5—Sn1—N1—C9 | 94.0 (3) | C9—C10—C11—C12 | −0.9 (6) |
C1—Sn1—N1—C9 | −81.9 (3) | C10—C11—C12—C13 | 0.2 (6) |
N2—Sn1—N1—C9 | −178.1 (3) | C10—C11—C12—C14 | −178.7 (4) |
Cl2—Sn1—N1—C9 | −166.5 (2) | C9—N1—C13—C12 | −1.0 (5) |
Cl1—Sn1—N1—C9 | 5.1 (3) | Sn1—N1—C13—C12 | −178.4 (3) |
C5—Sn1—N1—C13 | −88.8 (3) | C9—N1—C13—C17 | 179.0 (3) |
C1—Sn1—N1—C13 | 95.3 (3) | Sn1—N1—C13—C17 | 1.7 (4) |
N2—Sn1—N1—C13 | −0.9 (3) | C11—C12—C13—N1 | 0.8 (5) |
Cl2—Sn1—N1—C13 | 10.6 (5) | C14—C12—C13—N1 | 179.8 (4) |
Cl1—Sn1—N1—C13 | −177.7 (3) | C11—C12—C13—C17 | −179.3 (3) |
C5—Sn1—N2—C20 | −86.5 (3) | C14—C12—C13—C17 | −0.3 (5) |
C1—Sn1—N2—C20 | 97.7 (3) | C13—C12—C14—C15 | 0.9 (6) |
N1—Sn1—N2—C20 | −179.2 (3) | C11—C12—C14—C15 | 179.9 (4) |
Cl2—Sn1—N2—C20 | 4.2 (3) | C12—C14—C15—C16 | −0.7 (6) |
Cl1—Sn1—N2—C20 | −169.7 (2) | C14—C15—C16—C17 | −0.1 (6) |
C5—Sn1—N2—C17 | 92.7 (3) | C14—C15—C16—C18 | −178.5 (4) |
C1—Sn1—N2—C17 | −83.0 (3) | C20—N2—C17—C16 | −1.0 (5) |
N1—Sn1—N2—C17 | 0.0 (2) | Sn1—N2—C17—C16 | 179.7 (3) |
Cl2—Sn1—N2—C17 | −176.5 (2) | C20—N2—C17—C13 | −179.9 (3) |
Cl1—Sn1—N2—C17 | 9.6 (4) | Sn1—N2—C17—C13 | 0.8 (4) |
N2—Sn1—C1—C2 | −12.1 (3) | C18—C16—C17—N2 | 0.4 (5) |
N1—Sn1—C1—C2 | −81.4 (3) | C15—C16—C17—N2 | −178.1 (3) |
Cl2—Sn1—C1—C2 | 81.1 (3) | C18—C16—C17—C13 | 179.2 (3) |
Cl1—Sn1—C1—C2 | −172.7 (3) | C15—C16—C17—C13 | 0.7 (5) |
Sn1—C1—C2—C3 | −178.3 (3) | N1—C13—C17—N2 | −1.7 (5) |
C1—C2—C3—C4 | −58.7 (5) | C12—C13—C17—N2 | 178.4 (3) |
N2—Sn1—C5—C6 | −90.3 (3) | N1—C13—C17—C16 | 179.4 (3) |
N1—Sn1—C5—C6 | −20.5 (3) | C12—C13—C17—C16 | −0.5 (5) |
Cl2—Sn1—C5—C6 | 176.9 (3) | C17—C16—C18—C19 | 0.3 (5) |
Cl1—Sn1—C5—C6 | 70.5 (3) | C15—C16—C18—C19 | 178.7 (4) |
Sn1—C5—C6—C7 | 180.0 (3) | C16—C18—C19—C20 | −0.3 (6) |
C5—C6—C7—C8 | 175.7 (3) | C17—N2—C20—C19 | 1.0 (6) |
C13—N1—C9—C10 | 0.3 (6) | Sn1—N2—C20—C19 | −179.7 (3) |
Sn1—N1—C9—C10 | 177.4 (3) | C18—C19—C20—N2 | −0.4 (6) |
N1—C9—C10—C11 | 0.7 (6) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C4H9)2Cl2(C12H8N2)] |
Mr | 484.02 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.1400 (2), 10.4566 (2), 17.9375 (4) |
β (°) | 92.125 (2) |
V (Å3) | 2088.04 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 12.12 |
Crystal size (mm) | 0.20 × 0.10 × 0.02 |
Data collection | |
Diffractometer | Agilent SuperNova diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent Technologies, 2010) |
Tmin, Tmax | 0.196, 0.794 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15170, 11290, 10561 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.185, 1.08 |
No. of reflections | 11290 |
No. of parameters | 227 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.11, −1.95 |
Computer programs: CrysAlis PRO (Agilent Technologies, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
I thank the University of Malaya for supporting this study.
References
Agilent Technologies (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Ganis, P., Peruzzo, V. & Valle, G. (1983). J. Organomet. Chem. 256, 245–250. CSD CrossRef CAS Web of Science 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 di-n-butyltin dichloride adduct with 1,10-phenanthroline (Scheme I) belongs to the P212121 space group (Ganis et al., 1983). The complexation of the organotin halide with the N-heterocycle in ethanol solvent yielded a monoclinic modification as plate-like crystals that grew over one another. The molecule has the tin atom in an octahedral geometry (Fig. 1). The n-butyl groups are trans to each other whereas the chlorine atoms are cis to each other. The crystal studied is a non-merohedral twin with the minor domain being in a 15.8 (1)% proportion; the nature of the twin led to a moderately satisfactory weighting scheme in the refinement.