Abstract
In the title compound, [Sn(CH3)2(NSC)2(C24H16N2)], a 1:1 adduct of dimethyltin diisothiocyanate with 4,7-diphenyl-1,10-phenanthroline, the SnIV atom shows a slightly distorted octahedral SnC2N4 coordination. The methyl groups are trans to each other in the octahedron surrounding the metal atom [C—Sn—C = 176.61 (12)°].
Related literature
For the ethanol-solvated di-n-butyltin dichloride adduct of the N-heterocycle, see: Hu et al. (1989 ▶).
Experimental
Crystal data
[Sn(CH3)2(NSC)2(C24H16N2)]
M r = 597.31
Monoclinic,
a = 17.1918 (2) Å
b = 8.1907 (2) Å
c = 18.3045 (3) Å
β = 98.042 (1)°
V = 2552.16 (8) Å3
Z = 4
Mo Kα radiation
μ = 1.19 mm−1
T = 100 K
0.20 × 0.15 × 0.10 mm
Data collection
Agilent Technologies SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ▶) T min = 0.797, T max = 0.890
13167 measured reflections
5710 independent reflections
4833 reflections with I > 2σ(I)
R int = 0.031
Refinement
R[F 2 > 2σ(F 2)] = 0.034
wR(F 2) = 0.084
S = 1.03
5710 reflections
318 parameters
H-atom parameters constrained
Δρmax = 1.02 e Å−3
Δρmin = −0.89 e Å−3
Data collection: CrysAlis PRO (Agilent Technologies, 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 datablocks global, I. DOI: 10.1107/S1600536811001735/bt5462sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001735/bt5462Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank Shahid Beheshti University and the University of Malaya for supporting this study.
supplementary crystallographic information
Comment
Diorganotin dihalides/pseudohalides form a number of adducts with 1,10-phenanthroline and its derivatives. The dibutytlin dichloride adduct with 4,7-diphenyl-1,10-phenanthroline exists as an ethanol solvate (Hu et al., 1989). The dimethyltin diisothiocyanate adduct is anhydrous (Scheme I, Fig. 1). It also features the chelated tin atom in an octahedral geometry.
Experimental
Dimethyltin diisothiocyanate and 4,7-diphenyl-1,10-phenanthroline (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.
Refinement
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.
Figures
Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of Sn(NCS)2(CH3)2(C22H16N2)at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Crystal data
| [Sn(CH3)2(NSC)2(C24H16N2)] | F(000) = 1200 |
| Mr = 597.31 | Dx = 1.555 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 6689 reflections |
| a = 17.1918 (2) Å | θ = 2.2–29.4° |
| b = 8.1907 (2) Å | µ = 1.19 mm−1 |
| c = 18.3045 (3) Å | T = 100 K |
| β = 98.042 (1)° | Prism, colorless |
| V = 2552.16 (8) Å3 | 0.20 × 0.15 × 0.10 mm |
| Z = 4 |
Data collection
| Agilent Technologies SuperNova Dual (Cu at zero) diffractometer with an Atlas detector | 5710 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 4833 reflections with I > 2σ(I) |
| Mirror | Rint = 0.031 |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
| ω scans | h = −17→22 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010) | k = −10→8 |
| Tmin = 0.797, Tmax = 0.890 | l = −23→23 |
| 13167 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.084 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0372P)2 + 1.3448P] where P = (Fo2 + 2Fc2)/3 |
| 5710 reflections | (Δ/σ)max = 0.001 |
| 318 parameters | Δρmax = 1.02 e Å−3 |
| 0 restraints | Δρmin = −0.89 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Sn1 | 0.430971 (9) | 0.35713 (2) | 0.153313 (10) | 0.02007 (7) | |
| S1 | 0.39425 (6) | 0.14565 (14) | −0.10042 (6) | 0.0523 (3) | |
| S2 | 0.15135 (4) | 0.31635 (11) | 0.17421 (5) | 0.03287 (19) | |
| N1 | 0.50393 (11) | 0.4293 (3) | 0.26740 (12) | 0.0188 (5) | |
| N2 | 0.56572 (12) | 0.3760 (3) | 0.14104 (13) | 0.0183 (5) | |
| N3 | 0.39761 (16) | 0.3004 (3) | 0.03302 (14) | 0.0346 (6) | |
| N4 | 0.31366 (17) | 0.3499 (4) | 0.1919 (2) | 0.0528 (9) | |
| C1 | 0.44834 (17) | 0.1079 (4) | 0.17985 (18) | 0.0308 (7) | |
| H1A | 0.4090 | 0.0722 | 0.2104 | 0.046* | |
| H1B | 0.5011 | 0.0924 | 0.2072 | 0.046* | |
| H1C | 0.4430 | 0.0433 | 0.1344 | 0.046* | |
| C2 | 0.41642 (17) | 0.6092 (4) | 0.13329 (18) | 0.0291 (7) | |
| H2A | 0.3711 | 0.6271 | 0.0953 | 0.044* | |
| H2B | 0.4638 | 0.6534 | 0.1163 | 0.044* | |
| H2C | 0.4076 | 0.6645 | 0.1789 | 0.044* | |
| C3 | 0.59521 (15) | 0.3505 (4) | 0.07902 (16) | 0.0225 (6) | |
| H3 | 0.5613 | 0.3103 | 0.0375 | 0.027* | |
| C4 | 0.67354 (15) | 0.3796 (3) | 0.07169 (15) | 0.0207 (6) | |
| H4 | 0.6919 | 0.3584 | 0.0260 | 0.025* | |
| C5 | 0.72464 (14) | 0.4391 (3) | 0.13051 (15) | 0.0178 (5) | |
| C6 | 0.69505 (14) | 0.4625 (3) | 0.19856 (15) | 0.0169 (5) | |
| C7 | 0.61521 (14) | 0.4290 (3) | 0.20143 (14) | 0.0174 (5) | |
| C8 | 0.74140 (14) | 0.5247 (3) | 0.26383 (15) | 0.0196 (6) | |
| H8 | 0.7944 | 0.5553 | 0.2619 | 0.023* | |
| C9 | 0.71173 (14) | 0.5409 (4) | 0.32806 (15) | 0.0202 (6) | |
| H9 | 0.7451 | 0.5773 | 0.3707 | 0.024* | |
| C10 | 0.63136 (14) | 0.5044 (3) | 0.33323 (15) | 0.0171 (5) | |
| C11 | 0.58269 (13) | 0.4536 (3) | 0.26895 (14) | 0.0165 (5) | |
| C12 | 0.59669 (14) | 0.5299 (3) | 0.39857 (15) | 0.0176 (5) | |
| C13 | 0.51612 (14) | 0.5121 (4) | 0.39372 (15) | 0.0197 (6) | |
| H13 | 0.4906 | 0.5346 | 0.4354 | 0.024* | |
| C14 | 0.47207 (14) | 0.4613 (4) | 0.32769 (15) | 0.0208 (6) | |
| H14 | 0.4169 | 0.4491 | 0.3259 | 0.025* | |
| C15 | 0.80687 (14) | 0.4777 (3) | 0.11987 (15) | 0.0184 (6) | |
| C16 | 0.81958 (15) | 0.5699 (4) | 0.05879 (16) | 0.0230 (6) | |
| H16 | 0.7761 | 0.6070 | 0.0251 | 0.028* | |
| C17 | 0.89580 (17) | 0.6081 (4) | 0.04668 (18) | 0.0286 (7) | |
| H17 | 0.9042 | 0.6746 | 0.0060 | 0.034* | |
| C18 | 0.95916 (16) | 0.5487 (4) | 0.09433 (17) | 0.0290 (7) | |
| H18 | 1.0111 | 0.5734 | 0.0858 | 0.035* | |
| C19 | 0.94723 (15) | 0.4538 (4) | 0.15416 (16) | 0.0249 (6) | |
| H19 | 0.9910 | 0.4115 | 0.1860 | 0.030* | |
| C20 | 0.87128 (14) | 0.4198 (4) | 0.16795 (15) | 0.0204 (6) | |
| H20 | 0.8633 | 0.3574 | 0.2100 | 0.024* | |
| C21 | 0.64392 (14) | 0.5755 (3) | 0.46954 (14) | 0.0173 (5) | |
| C22 | 0.71205 (15) | 0.4890 (4) | 0.49706 (16) | 0.0228 (6) | |
| H22 | 0.7295 | 0.4020 | 0.4691 | 0.027* | |
| C23 | 0.75401 (15) | 0.5293 (4) | 0.56471 (16) | 0.0252 (6) | |
| H23 | 0.7995 | 0.4684 | 0.5834 | 0.030* | |
| C24 | 0.73016 (16) | 0.6579 (4) | 0.60538 (16) | 0.0246 (6) | |
| H24 | 0.7591 | 0.6851 | 0.6518 | 0.030* | |
| C25 | 0.66399 (15) | 0.7464 (4) | 0.57809 (15) | 0.0238 (6) | |
| H25 | 0.6484 | 0.8365 | 0.6053 | 0.029* | |
| C26 | 0.62034 (14) | 0.7044 (3) | 0.51140 (15) | 0.0185 (6) | |
| H26 | 0.5740 | 0.7637 | 0.4939 | 0.022* | |
| C27 | 0.39747 (15) | 0.2339 (4) | −0.02074 (18) | 0.0276 (7) | |
| C28 | 0.24557 (18) | 0.3359 (4) | 0.18306 (19) | 0.0323 (7) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.01425 (10) | 0.02700 (13) | 0.01784 (12) | −0.00130 (7) | −0.00165 (7) | 0.00103 (8) |
| S1 | 0.0643 (6) | 0.0581 (7) | 0.0384 (5) | −0.0235 (5) | 0.0209 (5) | −0.0208 (5) |
| S2 | 0.0185 (3) | 0.0407 (5) | 0.0401 (5) | −0.0003 (3) | 0.0063 (3) | 0.0046 (4) |
| N1 | 0.0156 (10) | 0.0238 (13) | 0.0168 (11) | −0.0006 (9) | 0.0011 (9) | 0.0047 (10) |
| N2 | 0.0172 (10) | 0.0224 (13) | 0.0150 (11) | −0.0005 (9) | 0.0010 (9) | 0.0011 (10) |
| N3 | 0.0547 (17) | 0.0268 (15) | 0.0194 (14) | 0.0013 (13) | −0.0052 (12) | −0.0013 (12) |
| N4 | 0.0261 (15) | 0.053 (2) | 0.083 (3) | −0.0066 (13) | 0.0204 (16) | −0.0049 (18) |
| C1 | 0.0262 (14) | 0.0320 (18) | 0.0321 (17) | −0.0039 (12) | −0.0038 (13) | 0.0119 (14) |
| C2 | 0.0287 (15) | 0.0300 (18) | 0.0275 (16) | 0.0092 (12) | 0.0004 (13) | 0.0032 (14) |
| C3 | 0.0210 (13) | 0.0283 (17) | 0.0169 (14) | −0.0005 (11) | −0.0017 (11) | 0.0015 (12) |
| C4 | 0.0206 (13) | 0.0257 (16) | 0.0161 (14) | 0.0016 (11) | 0.0037 (11) | 0.0004 (12) |
| C5 | 0.0189 (12) | 0.0152 (14) | 0.0198 (14) | 0.0023 (10) | 0.0042 (10) | 0.0011 (11) |
| C6 | 0.0151 (11) | 0.0163 (14) | 0.0196 (13) | 0.0001 (10) | 0.0038 (10) | −0.0008 (11) |
| C7 | 0.0159 (12) | 0.0173 (14) | 0.0184 (13) | 0.0011 (10) | 0.0000 (10) | 0.0032 (11) |
| C8 | 0.0150 (11) | 0.0192 (14) | 0.0248 (15) | −0.0007 (10) | 0.0042 (10) | −0.0043 (12) |
| C9 | 0.0151 (12) | 0.0243 (15) | 0.0207 (14) | −0.0010 (10) | 0.0008 (10) | −0.0038 (12) |
| C10 | 0.0184 (12) | 0.0133 (13) | 0.0194 (14) | 0.0013 (10) | 0.0026 (10) | 0.0025 (11) |
| C11 | 0.0151 (11) | 0.0155 (14) | 0.0185 (13) | −0.0004 (10) | 0.0013 (10) | 0.0016 (11) |
| C12 | 0.0175 (12) | 0.0164 (14) | 0.0191 (14) | 0.0017 (10) | 0.0027 (10) | 0.0028 (11) |
| C13 | 0.0189 (12) | 0.0241 (15) | 0.0170 (14) | 0.0007 (11) | 0.0054 (10) | 0.0031 (12) |
| C14 | 0.0152 (12) | 0.0295 (16) | 0.0177 (14) | −0.0023 (11) | 0.0025 (10) | 0.0041 (12) |
| C15 | 0.0190 (12) | 0.0161 (14) | 0.0212 (14) | 0.0004 (10) | 0.0070 (11) | −0.0067 (11) |
| C16 | 0.0250 (13) | 0.0191 (15) | 0.0254 (15) | 0.0019 (11) | 0.0057 (11) | −0.0014 (13) |
| C17 | 0.0326 (15) | 0.0247 (17) | 0.0315 (17) | −0.0055 (12) | 0.0148 (14) | −0.0041 (14) |
| C18 | 0.0230 (14) | 0.0298 (18) | 0.0365 (18) | −0.0092 (12) | 0.0125 (13) | −0.0131 (15) |
| C19 | 0.0166 (12) | 0.0310 (17) | 0.0266 (16) | −0.0002 (11) | 0.0021 (11) | −0.0131 (13) |
| C20 | 0.0213 (12) | 0.0199 (15) | 0.0203 (14) | −0.0014 (11) | 0.0047 (11) | −0.0064 (12) |
| C21 | 0.0174 (12) | 0.0188 (14) | 0.0160 (13) | −0.0029 (10) | 0.0031 (10) | 0.0004 (12) |
| C22 | 0.0211 (13) | 0.0184 (15) | 0.0281 (16) | −0.0003 (10) | 0.0014 (11) | −0.0013 (12) |
| C23 | 0.0179 (12) | 0.0290 (17) | 0.0269 (16) | 0.0004 (11) | −0.0030 (11) | 0.0037 (13) |
| C24 | 0.0205 (13) | 0.0340 (18) | 0.0191 (15) | −0.0082 (12) | 0.0016 (11) | −0.0003 (13) |
| C25 | 0.0271 (14) | 0.0257 (16) | 0.0204 (15) | −0.0036 (12) | 0.0102 (11) | −0.0046 (13) |
| C26 | 0.0167 (12) | 0.0197 (14) | 0.0192 (14) | −0.0005 (10) | 0.0034 (10) | 0.0016 (12) |
| C27 | 0.0185 (13) | 0.0306 (18) | 0.0321 (18) | −0.0043 (12) | −0.0017 (12) | 0.0093 (15) |
| C28 | 0.0285 (16) | 0.0304 (18) | 0.040 (2) | −0.0006 (12) | 0.0132 (14) | 0.0021 (15) |
Geometric parameters (Å, °)
| Sn1—C2 | 2.106 (3) | C9—C10 | 1.430 (3) |
| Sn1—C1 | 2.110 (3) | C9—H9 | 0.9500 |
| Sn1—N4 | 2.229 (3) | C10—C11 | 1.408 (4) |
| Sn1—N3 | 2.245 (3) | C10—C12 | 1.424 (4) |
| Sn1—N1 | 2.356 (2) | C12—C13 | 1.383 (3) |
| Sn1—N2 | 2.364 (2) | C12—C21 | 1.480 (4) |
| S1—C27 | 1.622 (3) | C13—C14 | 1.397 (4) |
| S2—C28 | 1.613 (3) | C13—H13 | 0.9500 |
| N1—C14 | 1.325 (3) | C14—H14 | 0.9500 |
| N1—C11 | 1.365 (3) | C15—C16 | 1.392 (4) |
| N2—C3 | 1.323 (4) | C15—C20 | 1.397 (4) |
| N2—C7 | 1.368 (3) | C16—C17 | 1.395 (4) |
| N3—C27 | 1.125 (4) | C16—H16 | 0.9500 |
| N4—C28 | 1.165 (4) | C17—C18 | 1.385 (4) |
| C1—H1A | 0.9800 | C17—H17 | 0.9500 |
| C1—H1B | 0.9800 | C18—C19 | 1.382 (4) |
| C1—H1C | 0.9800 | C18—H18 | 0.9500 |
| C2—H2A | 0.9800 | C19—C20 | 1.392 (3) |
| C2—H2B | 0.9800 | C19—H19 | 0.9500 |
| C2—H2C | 0.9800 | C20—H20 | 0.9500 |
| C3—C4 | 1.392 (4) | C21—C26 | 1.397 (4) |
| C3—H3 | 0.9500 | C21—C22 | 1.401 (4) |
| C4—C5 | 1.380 (4) | C22—C23 | 1.383 (4) |
| C4—H4 | 0.9500 | C22—H22 | 0.9500 |
| C5—C6 | 1.423 (4) | C23—C24 | 1.384 (4) |
| C5—C15 | 1.488 (3) | C23—H23 | 0.9500 |
| C6—C7 | 1.408 (3) | C24—C25 | 1.382 (4) |
| C6—C8 | 1.434 (4) | C24—H24 | 0.9500 |
| C7—C11 | 1.440 (4) | C25—C26 | 1.384 (4) |
| C8—C9 | 1.352 (4) | C25—H25 | 0.9500 |
| C8—H8 | 0.9500 | C26—H26 | 0.9500 |
| C2—Sn1—C1 | 176.61 (12) | C10—C9—H9 | 119.2 |
| C2—Sn1—N4 | 89.45 (12) | C11—C10—C12 | 118.4 (2) |
| C1—Sn1—N4 | 90.38 (12) | C11—C10—C9 | 118.2 (2) |
| C2—Sn1—N3 | 91.41 (12) | C12—C10—C9 | 123.1 (2) |
| C1—Sn1—N3 | 91.95 (12) | N1—C11—C10 | 122.2 (2) |
| N4—Sn1—N3 | 100.76 (12) | N1—C11—C7 | 117.7 (2) |
| C2—Sn1—N1 | 86.78 (11) | C10—C11—C7 | 120.1 (2) |
| C1—Sn1—N1 | 89.89 (11) | C13—C12—C10 | 117.6 (2) |
| N4—Sn1—N1 | 96.84 (11) | C13—C12—C21 | 120.3 (2) |
| N3—Sn1—N1 | 162.29 (9) | C10—C12—C21 | 122.1 (2) |
| C2—Sn1—N2 | 90.76 (10) | C12—C13—C14 | 120.2 (2) |
| C1—Sn1—N2 | 88.64 (10) | C12—C13—H13 | 119.9 |
| N4—Sn1—N2 | 166.95 (11) | C14—C13—H13 | 119.9 |
| N3—Sn1—N2 | 92.27 (9) | N1—C14—C13 | 122.9 (2) |
| N1—Sn1—N2 | 70.15 (7) | N1—C14—H14 | 118.6 |
| C14—N1—C11 | 118.6 (2) | C13—C14—H14 | 118.6 |
| C14—N1—Sn1 | 123.85 (16) | C16—C15—C20 | 119.4 (2) |
| C11—N1—Sn1 | 117.30 (16) | C16—C15—C5 | 118.7 (2) |
| C3—N2—C7 | 118.3 (2) | C20—C15—C5 | 122.0 (2) |
| C3—N2—Sn1 | 124.71 (18) | C15—C16—C17 | 120.4 (3) |
| C7—N2—Sn1 | 116.81 (16) | C15—C16—H16 | 119.8 |
| C27—N3—Sn1 | 158.1 (3) | C17—C16—H16 | 119.8 |
| C28—N4—Sn1 | 153.5 (3) | C18—C17—C16 | 119.6 (3) |
| Sn1—C1—H1A | 109.5 | C18—C17—H17 | 120.2 |
| Sn1—C1—H1B | 109.5 | C16—C17—H17 | 120.2 |
| H1A—C1—H1B | 109.5 | C19—C18—C17 | 120.4 (2) |
| Sn1—C1—H1C | 109.5 | C19—C18—H18 | 119.8 |
| H1A—C1—H1C | 109.5 | C17—C18—H18 | 119.8 |
| H1B—C1—H1C | 109.5 | C18—C19—C20 | 120.2 (3) |
| Sn1—C2—H2A | 109.5 | C18—C19—H19 | 119.9 |
| Sn1—C2—H2B | 109.5 | C20—C19—H19 | 119.9 |
| H2A—C2—H2B | 109.5 | C19—C20—C15 | 119.9 (3) |
| Sn1—C2—H2C | 109.5 | C19—C20—H20 | 120.0 |
| H2A—C2—H2C | 109.5 | C15—C20—H20 | 120.0 |
| H2B—C2—H2C | 109.5 | C26—C21—C22 | 118.5 (2) |
| N2—C3—C4 | 123.2 (3) | C26—C21—C12 | 120.4 (2) |
| N2—C3—H3 | 118.4 | C22—C21—C12 | 121.1 (3) |
| C4—C3—H3 | 118.4 | C23—C22—C21 | 120.4 (3) |
| C5—C4—C3 | 120.3 (3) | C23—C22—H22 | 119.8 |
| C5—C4—H4 | 119.9 | C21—C22—H22 | 119.8 |
| C3—C4—H4 | 119.9 | C22—C23—C24 | 120.4 (3) |
| C4—C5—C6 | 117.6 (2) | C22—C23—H23 | 119.8 |
| C4—C5—C15 | 119.1 (2) | C24—C23—H23 | 119.8 |
| C6—C5—C15 | 123.3 (2) | C25—C24—C23 | 119.7 (3) |
| C7—C6—C5 | 118.4 (2) | C25—C24—H24 | 120.2 |
| C7—C6—C8 | 118.0 (2) | C23—C24—H24 | 120.2 |
| C5—C6—C8 | 123.5 (2) | C24—C25—C26 | 120.4 (3) |
| N2—C7—C6 | 122.1 (2) | C24—C25—H25 | 119.8 |
| N2—C7—C11 | 117.8 (2) | C26—C25—H25 | 119.8 |
| C6—C7—C11 | 120.1 (2) | C25—C26—C21 | 120.6 (2) |
| C9—C8—C6 | 121.8 (2) | C25—C26—H26 | 119.7 |
| C9—C8—H8 | 119.1 | C21—C26—H26 | 119.7 |
| C6—C8—H8 | 119.1 | N3—C27—S1 | 176.9 (3) |
| C8—C9—C10 | 121.5 (2) | N4—C28—S2 | 177.8 (4) |
| C8—C9—H9 | 119.2 | ||
| C2—Sn1—N1—C14 | 85.1 (2) | C8—C9—C10—C11 | −1.2 (4) |
| C1—Sn1—N1—C14 | −94.3 (2) | C8—C9—C10—C12 | −175.8 (3) |
| N4—Sn1—N1—C14 | −3.9 (2) | C14—N1—C11—C10 | 2.8 (4) |
| N3—Sn1—N1—C14 | 169.6 (3) | Sn1—N1—C11—C10 | 177.00 (19) |
| N2—Sn1—N1—C14 | 177.1 (2) | C14—N1—C11—C7 | −175.8 (2) |
| C2—Sn1—N1—C11 | −88.7 (2) | Sn1—N1—C11—C7 | −1.6 (3) |
| C1—Sn1—N1—C11 | 91.9 (2) | C12—C10—C11—N1 | 0.4 (4) |
| N4—Sn1—N1—C11 | −177.7 (2) | C9—C10—C11—N1 | −174.5 (3) |
| N3—Sn1—N1—C11 | −4.2 (4) | C12—C10—C11—C7 | 179.0 (2) |
| N2—Sn1—N1—C11 | 3.29 (19) | C9—C10—C11—C7 | 4.1 (4) |
| C2—Sn1—N2—C3 | −93.4 (2) | N2—C7—C11—N1 | −2.8 (4) |
| C1—Sn1—N2—C3 | 89.9 (2) | C6—C7—C11—N1 | 175.9 (3) |
| N4—Sn1—N2—C3 | 175.8 (4) | N2—C7—C11—C10 | 178.6 (2) |
| N3—Sn1—N2—C3 | −2.0 (2) | C6—C7—C11—C10 | −2.8 (4) |
| N1—Sn1—N2—C3 | −179.7 (2) | C11—C10—C12—C13 | −3.6 (4) |
| C2—Sn1—N2—C7 | 81.6 (2) | C9—C10—C12—C13 | 171.0 (3) |
| C1—Sn1—N2—C7 | −95.1 (2) | C11—C10—C12—C21 | 177.0 (3) |
| N4—Sn1—N2—C7 | −9.3 (6) | C9—C10—C12—C21 | −8.4 (4) |
| N3—Sn1—N2—C7 | 173.0 (2) | C10—C12—C13—C14 | 3.7 (4) |
| N1—Sn1—N2—C7 | −4.72 (18) | C21—C12—C13—C14 | −176.8 (3) |
| C2—Sn1—N3—C27 | 147.3 (7) | C11—N1—C14—C13 | −2.8 (4) |
| C1—Sn1—N3—C27 | −32.2 (7) | Sn1—N1—C14—C13 | −176.6 (2) |
| N4—Sn1—N3—C27 | −123.0 (7) | C12—C13—C14—N1 | −0.5 (4) |
| N1—Sn1—N3—C27 | 63.5 (8) | C4—C5—C15—C16 | 47.9 (4) |
| N2—Sn1—N3—C27 | 56.5 (7) | C6—C5—C15—C16 | −131.2 (3) |
| C2—Sn1—N4—C28 | 88.5 (7) | C4—C5—C15—C20 | −130.0 (3) |
| C1—Sn1—N4—C28 | −94.8 (7) | C6—C5—C15—C20 | 50.9 (4) |
| N3—Sn1—N4—C28 | −2.8 (7) | C20—C15—C16—C17 | −1.8 (4) |
| N1—Sn1—N4—C28 | 175.2 (7) | C5—C15—C16—C17 | −179.7 (3) |
| N2—Sn1—N4—C28 | 179.5 (5) | C15—C16—C17—C18 | 2.4 (4) |
| C7—N2—C3—C4 | −2.0 (4) | C16—C17—C18—C19 | −0.8 (5) |
| Sn1—N2—C3—C4 | 172.9 (2) | C17—C18—C19—C20 | −1.4 (4) |
| N2—C3—C4—C5 | −0.5 (4) | C18—C19—C20—C15 | 2.0 (4) |
| C3—C4—C5—C6 | 2.5 (4) | C16—C15—C20—C19 | −0.4 (4) |
| C3—C4—C5—C15 | −176.6 (3) | C5—C15—C20—C19 | 177.5 (3) |
| C4—C5—C6—C7 | −2.0 (4) | C13—C12—C21—C26 | −47.3 (4) |
| C15—C5—C6—C7 | 177.1 (3) | C10—C12—C21—C26 | 132.1 (3) |
| C4—C5—C6—C8 | −179.4 (3) | C13—C12—C21—C22 | 131.4 (3) |
| C15—C5—C6—C8 | −0.3 (4) | C10—C12—C21—C22 | −49.3 (4) |
| C3—N2—C7—C6 | 2.4 (4) | C26—C21—C22—C23 | 1.0 (4) |
| Sn1—N2—C7—C6 | −172.9 (2) | C12—C21—C22—C23 | −177.7 (3) |
| C3—N2—C7—C11 | −178.9 (2) | C21—C22—C23—C24 | −1.3 (4) |
| Sn1—N2—C7—C11 | 5.8 (3) | C22—C23—C24—C25 | 0.0 (4) |
| C5—C6—C7—N2 | −0.4 (4) | C23—C24—C25—C26 | 1.8 (4) |
| C8—C6—C7—N2 | 177.1 (2) | C24—C25—C26—C21 | −2.1 (4) |
| C5—C6—C7—C11 | −179.0 (2) | C22—C21—C26—C25 | 0.8 (4) |
| C8—C6—C7—C11 | −1.4 (4) | C12—C21—C26—C25 | 179.4 (2) |
| C7—C6—C8—C9 | 4.5 (4) | Sn1—N3—C27—S1 | −174 (5) |
| C5—C6—C8—C9 | −178.1 (3) | Sn1—N4—C28—S2 | 171 (8) |
| C6—C8—C9—C10 | −3.2 (4) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5462).
References
- Agilent Technologies (2010). CrysAlis PRO Agilent Technologies, Yarnton, England.
- Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
- Hu, S.-Z., Lin, W.-F., Wan, J. Z. & Huang, Z.-X. (1989). Chin. J. Struct. Chem. 8, 36–39.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- 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 datablocks global, I. DOI: 10.1107/S1600536811001735/bt5462sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001735/bt5462Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report

