Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620016502/cu3168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620016502/cu3168Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620016502/cu3168IIsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620016502/cu3168sup4.pdf |
CCDC references: 2051766; 2051765
Data collection: CrysAlis PRO (Agilent, 2014) for (I); CrystalClear-SM Expert (Rigaku, 2011) for (II). Cell refinement: CrysAlis PRO (Agilent, 2014) for (I); CrystalClear-SM Expert (Rigaku, 2011) for (II). Data reduction: CrysAlis PRO (Agilent, 2014) for (I); CrystalClear-SM Expert (Rigaku, 2011) for (II). For both structures, program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a). Program(s) used to refine structure: JANA2006 (Petříček et al., 2014) for (I); SHELXL2018 (Sheldrick, 2015b) for (II). Software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009), SUPERFLIP (Palatinus & Chapuis, 2007) and pyMOL (Schrödinger, 2015) for (I); SHELXL2018 (Sheldrick, 2015b) for (II).
[Sn(CH3)2(C21H21Cl3N3OP)2Cl2] | F(000) = 1172 |
Mr = 1157.2 | Dx = 1.531 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2yabc | Cell parameters from 9555 reflections |
a = 15.4589 (4) Å | θ = 4.2–67.0° |
b = 8.1983 (3) Å | µ = 8.92 mm−1 |
c = 20.6655 (6) Å | T = 120 K |
β = 106.556 (2)° | Polygon shape, colour less |
V = 2510.50 (14) Å3 | 0.18 × 0.13 × 0.10 mm |
Z = 2 |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 4433 independent reflections |
Radiation source: X-ray tube | 4052 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.037 |
Detector resolution: 5.1873 pixels mm-1 | θmax = 67.1°, θmin = 3.2° |
ω scans | h = −16→18 |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)] | k = −8→9 |
Tmin = 0.304, Tmax = 0.523 | l = −24→24 |
15856 measured reflections |
Refinement on F2 | 84 constraints |
R[F > 3σ(F)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F) = 0.058 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 1.31 | (Δ/σ)max = 0.014 |
4433 reflections | Δρmax = 0.30 e Å−3 |
298 parameters | Δρmin = −0.39 e Å−3 |
2 restraints |
Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program. The structure of (I) was refined with program Jana2006 (Petříček et al., 2014), the structure (II) was refined using SHELXL2018/3 (Sheldrick, 2015b), and the refinement parameters are summarized in Table 1. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0 | 0.5 | 0 | 0.01668 (6) | |
Cl1 | −0.13615 (3) | 0.38646 (6) | 0.03603 (3) | 0.02572 (16) | |
Cl2 | 0.34145 (3) | −0.14768 (6) | −0.01587 (3) | 0.02642 (16) | |
P1 | 0.08493 (3) | 0.12750 (6) | −0.04461 (2) | 0.01583 (14) | |
Cl3 | 0.25921 (5) | 0.01666 (8) | −0.23780 (3) | 0.0474 (2) | |
Cl4 | −0.22086 (5) | 0.08893 (11) | −0.26114 (4) | 0.0687 (3) | |
O1 | 0.04992 (9) | 0.24649 (16) | −0.00228 (7) | 0.0190 (4) | |
N1 | 0.11458 (11) | 0.2368 (2) | −0.10065 (8) | 0.0194 (5) | |
N2 | 0.16346 (11) | 0.0155 (2) | 0.00550 (9) | 0.0190 (5) | |
N3 | 0.01782 (12) | −0.0128 (2) | −0.08618 (9) | 0.0204 (5) | |
C16 | −0.06141 (14) | 0.0225 (3) | −0.14235 (11) | 0.0235 (6) | |
C17 | −0.06532 (14) | −0.0735 (2) | −0.20564 (10) | 0.0235 (6) | |
C5 | 0.12183 (17) | 0.1473 (3) | −0.33444 (12) | 0.0339 (8) | |
C2 | 0.16514 (13) | 0.1685 (3) | −0.14428 (10) | 0.0232 (6) | |
C14 | 0.37903 (14) | 0.3951 (3) | −0.01593 (12) | 0.0295 (7) | |
C15 | 0.32245 (13) | 0.3277 (3) | 0.01821 (11) | 0.0249 (7) | |
C9 | 0.24318 (13) | 0.0882 (3) | 0.05328 (10) | 0.0223 (6) | |
C8 | 0.04044 (14) | 0.2787 (3) | −0.24334 (11) | 0.0268 (7) | |
C3 | 0.11991 (13) | 0.1919 (2) | −0.21875 (10) | 0.0208 (6) | |
C20 | −0.0765 (2) | −0.2436 (3) | −0.32497 (13) | 0.0449 (9) | |
C4 | 0.15926 (15) | 0.1271 (3) | −0.26593 (11) | 0.0269 (7) | |
C10 | 0.30944 (13) | 0.1598 (2) | 0.01952 (10) | 0.0204 (6) | |
C13 | 0.42332 (14) | 0.2962 (3) | −0.05038 (11) | 0.0285 (7) | |
C12 | 0.41241 (13) | 0.1284 (3) | −0.04970 (11) | 0.0247 (6) | |
C22 | 0.00145 (15) | −0.1828 (3) | −0.20933 (12) | 0.0296 (7) | |
C21 | −0.00374 (18) | −0.2673 (3) | −0.26855 (13) | 0.0405 (9) | |
C11 | 0.35636 (13) | 0.0631 (2) | −0.01493 (10) | 0.0215 (6) | |
C19 | −0.1439 (2) | −0.1358 (3) | −0.32260 (13) | 0.0448 (9) | |
C7 | 0.00087 (15) | 0.2975 (3) | −0.31234 (12) | 0.0329 (7) | |
C6 | 0.04183 (17) | 0.2325 (3) | −0.35783 (12) | 0.0357 (8) | |
C18 | −0.13698 (16) | −0.0517 (3) | −0.26315 (13) | 0.0359 (8) | |
C1 | −0.07834 (15) | 0.4897 (3) | −0.10179 (11) | 0.0266 (7) | |
H1c16 | −0.063416 | 0.13711 | −0.152283 | 0.0282* | |
H2c16 | −0.114961 | 0.001993 | −0.128924 | 0.0282* | |
H1c5 | 0.151107 | 0.102627 | −0.365653 | 0.0407* | |
H1c2 | 0.175352 | 0.054323 | −0.134806 | 0.0279* | |
H2c2 | 0.224427 | 0.215612 | −0.132767 | 0.0279* | |
H1c14 | 0.387519 | 0.511141 | −0.015656 | 0.0354* | |
H1c15 | 0.291606 | 0.398173 | 0.041431 | 0.0299* | |
H1c9 | 0.273069 | 0.00746 | 0.085583 | 0.0267* | |
H2c9 | 0.224415 | 0.171242 | 0.079139 | 0.0267* | |
H1c8 | 0.012151 | 0.326758 | −0.212181 | 0.0322* | |
H1c20 | −0.080017 | −0.302366 | −0.365826 | 0.0539* | |
H1c13 | 0.461522 | 0.34361 | −0.074716 | 0.0342* | |
H1c12 | 0.443375 | 0.05856 | −0.073057 | 0.0297* | |
H1c22 | 0.052042 | −0.200373 | −0.170377 | 0.0356* | |
H1c21 | 0.043216 | −0.342302 | −0.270356 | 0.0486* | |
H1c19 | −0.194843 | −0.119298 | −0.361433 | 0.0538* | |
H1c7 | −0.055023 | 0.35581 | −0.328388 | 0.0395* | |
H1c6 | 0.014855 | 0.246337 | −0.405454 | 0.0428* | |
H1c1 | −0.113287 | 0.391083 | −0.109381 | 0.0319* | |
H2c1 | −0.118083 | 0.582075 | −0.111778 | 0.0319* | |
H3c1 | −0.039309 | 0.491187 | −0.130541 | 0.0319* | |
H1N3 | 0.0131 (16) | −0.098 (2) | −0.0650 (11) | 0.023 (6)* | |
H1N1 | 0.1277 (15) | 0.335 (2) | −0.0901 (12) | 0.019 (6)* | |
H1N2 | 0.1695 (16) | −0.081 (2) | −0.0059 (12) | 0.026 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01683 (10) | 0.01580 (10) | 0.01579 (10) | 0.00129 (6) | 0.00204 (7) | −0.00065 (6) |
Cl1 | 0.0239 (2) | 0.0195 (2) | 0.0359 (3) | −0.00104 (18) | 0.0119 (2) | −0.00049 (19) |
Cl2 | 0.0255 (2) | 0.0207 (2) | 0.0349 (3) | 0.00237 (19) | 0.0115 (2) | −0.0005 (2) |
P1 | 0.0161 (2) | 0.0166 (2) | 0.0144 (2) | 0.00089 (18) | 0.00391 (18) | −0.00005 (18) |
Cl3 | 0.0548 (4) | 0.0530 (4) | 0.0419 (4) | 0.0278 (3) | 0.0255 (3) | 0.0051 (3) |
Cl4 | 0.0468 (4) | 0.0698 (5) | 0.0617 (5) | 0.0226 (4) | −0.0292 (3) | −0.0192 (4) |
O1 | 0.0209 (6) | 0.0173 (6) | 0.0188 (7) | 0.0027 (5) | 0.0058 (5) | 0.0008 (5) |
N1 | 0.0233 (8) | 0.0163 (8) | 0.0193 (8) | 0.0008 (7) | 0.0070 (7) | 0.0000 (7) |
N2 | 0.0198 (8) | 0.0177 (8) | 0.0187 (8) | 0.0020 (6) | 0.0040 (7) | −0.0013 (6) |
N3 | 0.0244 (9) | 0.0188 (9) | 0.0163 (8) | −0.0019 (7) | 0.0030 (7) | 0.0009 (6) |
C16 | 0.0191 (10) | 0.0273 (11) | 0.0217 (11) | −0.0001 (8) | 0.0018 (8) | −0.0024 (8) |
C17 | 0.0260 (10) | 0.0218 (10) | 0.0208 (10) | −0.0085 (8) | 0.0038 (8) | −0.0017 (8) |
C5 | 0.0499 (14) | 0.0310 (12) | 0.0230 (11) | −0.0079 (11) | 0.0138 (10) | −0.0071 (9) |
C2 | 0.0230 (10) | 0.0283 (11) | 0.0202 (10) | 0.0042 (8) | 0.0092 (8) | 0.0037 (8) |
C14 | 0.0275 (11) | 0.0231 (11) | 0.0321 (12) | −0.0002 (9) | −0.0007 (9) | 0.0040 (9) |
C15 | 0.0221 (10) | 0.0241 (11) | 0.0246 (11) | 0.0026 (8) | 0.0004 (8) | −0.0025 (8) |
C9 | 0.0201 (9) | 0.0276 (11) | 0.0168 (10) | 0.0044 (8) | 0.0016 (8) | −0.0004 (8) |
C8 | 0.0248 (10) | 0.0327 (11) | 0.0229 (11) | −0.0001 (9) | 0.0067 (9) | 0.0026 (9) |
C3 | 0.0233 (10) | 0.0197 (9) | 0.0201 (10) | −0.0050 (8) | 0.0073 (8) | 0.0012 (8) |
C20 | 0.0628 (17) | 0.0484 (15) | 0.0255 (13) | −0.0212 (14) | 0.0156 (12) | −0.0141 (11) |
C4 | 0.0326 (11) | 0.0225 (10) | 0.0276 (11) | −0.0001 (9) | 0.0118 (9) | −0.0010 (9) |
C10 | 0.0166 (9) | 0.0240 (10) | 0.0164 (9) | 0.0024 (8) | −0.0023 (7) | 0.0002 (8) |
C13 | 0.0218 (10) | 0.0332 (12) | 0.0283 (11) | −0.0016 (9) | 0.0037 (9) | 0.0077 (9) |
C12 | 0.0183 (9) | 0.0295 (11) | 0.0250 (11) | 0.0034 (8) | 0.0039 (8) | 0.0011 (9) |
C22 | 0.0330 (11) | 0.0293 (11) | 0.0257 (11) | −0.0037 (9) | 0.0069 (9) | −0.0058 (9) |
C21 | 0.0470 (14) | 0.0403 (14) | 0.0379 (14) | −0.0075 (12) | 0.0179 (12) | −0.0159 (11) |
C11 | 0.0186 (9) | 0.0207 (10) | 0.0220 (10) | 0.0012 (8) | 0.0006 (8) | 0.0015 (8) |
C19 | 0.0555 (16) | 0.0458 (15) | 0.0221 (12) | −0.0148 (13) | −0.0067 (11) | −0.0015 (11) |
C7 | 0.0278 (11) | 0.0430 (13) | 0.0240 (11) | −0.0039 (10) | 0.0010 (9) | 0.0071 (10) |
C6 | 0.0425 (13) | 0.0426 (13) | 0.0182 (11) | −0.0157 (11) | 0.0026 (10) | −0.0007 (10) |
C18 | 0.0346 (12) | 0.0337 (12) | 0.0319 (13) | −0.0038 (10) | −0.0027 (10) | −0.0027 (10) |
C1 | 0.0274 (11) | 0.0290 (11) | 0.0189 (10) | 0.0054 (8) | −0.0004 (9) | −0.0034 (8) |
Sn1—Cl1 | 2.5970 (5) | C15—C10 | 1.393 (3) |
Sn1—Cl1i | 2.5970 (5) | C15—H1c15 | 0.96 |
Sn1—C1 | 2.109 (2) | C9—C10 | 1.513 (3) |
Sn1—C1i | 2.109 (2) | C9—H1c9 | 0.96 |
Sn1—O1 | 2.2222 (13) | C9—H2c9 | 0.96 |
P1—O1 | 1.5099 (15) | C8—C3 | 1.385 (3) |
P1—N1 | 1.6299 (19) | C8—C7 | 1.391 (3) |
P1—N2 | 1.6348 (16) | C8—H1c8 | 0.96 |
P1—N3 | 1.6212 (16) | C3—C4 | 1.393 (3) |
N1—C2 | 1.462 (3) | C20—C21 | 1.384 (3) |
N1—H1N1 | 0.841 (17) | C20—C19 | 1.378 (4) |
N2—C9 | 1.468 (2) | C20—H1c20 | 0.96 |
N2—H1N2 | 0.841 (18) | C10—C11 | 1.398 (3) |
N3—C16 | 1.457 (2) | C13—C12 | 1.387 (3) |
N3—H1N3 | 0.84 (2) | C13—H1c13 | 0.96 |
C16—C17 | 1.513 (3) | C12—C11 | 1.381 (3) |
C16—H1c16 | 0.96 | C12—H1c12 | 0.96 |
C16—H2c16 | 0.96 | C22—C21 | 1.389 (4) |
C17—C22 | 1.385 (3) | C22—H1c22 | 0.96 |
C17—C18 | 1.386 (3) | C21—H1c21 | 0.96 |
C5—C4 | 1.378 (3) | C19—C18 | 1.386 (4) |
C5—C6 | 1.382 (3) | C19—H1c19 | 0.96 |
C5—H1c5 | 0.96 | C7—C6 | 1.381 (4) |
C2—C3 | 1.510 (3) | C7—H1c7 | 0.96 |
C2—H1c2 | 0.96 | C6—H1c6 | 0.96 |
C2—H2c2 | 0.96 | C1—H1c1 | 0.96 |
C14—C15 | 1.386 (3) | C1—H2c1 | 0.96 |
C14—C13 | 1.382 (3) | C1—H3c1 | 0.96 |
C14—H1c14 | 0.96 | ||
Sn1—O1—P1 | 143.18 (9) | C10—C15—H1c15 | 119.34 |
N2—H1N2—Cl2 | 113.1 (19) | N2—C9—C10 | 113.35 (17) |
N2—H1N2—Cl1ii | 161 (2) | N2—C9—H1c9 | 109.47 |
Cl1—Sn1—Cl1i | 180 | N2—C9—H2c9 | 109.47 |
Cl1—Sn1—C1 | 89.41 (7) | C10—C9—H1c9 | 109.47 |
Cl1—Sn1—C1i | 90.59 (7) | C10—C9—H2c9 | 109.47 |
Cl1i—Sn1—C1 | 90.59 (7) | H1c9—C9—H2c9 | 105.29 |
Cl1i—Sn1—C1i | 89.41 (7) | C3—C8—C7 | 121.2 (2) |
C1—Sn1—C1i | 180 | C3—C8—H1c8 | 119.39 |
Sn1—Cl1—N1i | 77.68 (3) | C7—C8—H1c8 | 119.39 |
O1—P1—N1 | 106.04 (8) | C2—C3—C8 | 123.0 (2) |
O1—P1—N2 | 108.65 (8) | C2—C3—C4 | 119.79 (17) |
O1—P1—N3 | 118.97 (9) | C8—C3—C4 | 117.25 (18) |
O1—Sn1—Cl1 | 89.17 (5) | C21—C20—C19 | 120.1 (3) |
O1—Sn1—C1 | 92.61 (8) | C21—C20—H1c20 | 119.95 |
N1—P1—N2 | 116.77 (9) | C19—C20—H1c20 | 119.95 |
N1—P1—N3 | 106.29 (9) | C5—C4—C3 | 122.2 (2) |
N2—P1—N3 | 100.66 (8) | C15—C10—C9 | 120.87 (19) |
P1—N1—C2 | 122.37 (14) | C15—C10—C11 | 116.9 (2) |
P1—N1—H1N1 | 115.9 (18) | C9—C10—C11 | 122.18 (18) |
C2—N1—H1N1 | 113.2 (18) | C14—C13—C12 | 119.8 (2) |
P1—N2—C9 | 121.85 (13) | C14—C13—H1c13 | 120.1 |
P1—N2—H1N2 | 118.3 (15) | C12—C13—H1c13 | 120.1 |
C9—N2—H1N2 | 115.7 (15) | C13—C12—C11 | 119.1 (2) |
P1—N3—C16 | 123.18 (13) | C13—C12—H1c12 | 120.47 |
P1—N3—H1N3 | 116.9 (14) | C11—C12—H1c12 | 120.47 |
C16—N3—H1N3 | 113.8 (14) | C17—C22—C21 | 121.0 (2) |
N3—C16—C17 | 113.77 (17) | C17—C22—H1c22 | 119.52 |
N3—C16—H1c16 | 109.47 | C21—C22—H1c22 | 119.52 |
N3—C16—H2c16 | 109.47 | C20—C21—C22 | 120.1 (3) |
C17—C16—H1c16 | 109.47 | C20—C21—H1c21 | 119.95 |
C17—C16—H2c16 | 109.47 | C22—C21—H1c21 | 119.95 |
H1c16—C16—H2c16 | 104.81 | C10—C11—C12 | 122.59 (19) |
C16—C17—C22 | 122.50 (17) | C20—C19—C18 | 118.8 (2) |
C16—C17—C18 | 120.0 (2) | C20—C19—H1c19 | 120.59 |
C22—C17—C18 | 117.5 (2) | C18—C19—H1c19 | 120.59 |
C4—C5—C6 | 119.5 (2) | C8—C7—C6 | 120.1 (2) |
C4—C5—H1c5 | 120.26 | C8—C7—H1c7 | 119.94 |
C6—C5—H1c5 | 120.26 | C6—C7—H1c7 | 119.94 |
N1—C2—C3 | 113.95 (16) | C5—C6—C7 | 119.7 (2) |
N1—C2—H1c2 | 109.47 | C5—C6—H1c6 | 120.16 |
N1—C2—H2c2 | 109.47 | C7—C6—H1c6 | 120.16 |
C3—C2—H1c2 | 109.47 | C17—C18—C19 | 122.5 (2) |
C3—C2—H2c2 | 109.47 | Sn1—C1—H1c1 | 109.47 |
H1c2—C2—H2c2 | 104.59 | Sn1—C1—H2c1 | 109.47 |
C15—C14—C13 | 120.4 (2) | Sn1—C1—H3c1 | 109.47 |
C15—C14—H1c14 | 119.81 | H1c1—C1—H2c1 | 109.47 |
C13—C14—H1c14 | 119.81 | H1c1—C1—H3c1 | 109.47 |
C14—C15—C10 | 121.3 (2) | H2c1—C1—H3c1 | 109.47 |
C14—C15—H1c15 | 119.35 | ||
N3—C16—C17—C22 | −0.8 (3) | N2—C9—C10—C15 | 111.1 (2) |
N1—C2—C3—C8 | 3.6 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N3···O1ii | 0.84 (2) | 2.26 (2) | 3.033 (2) | 152 (2) |
N1—H1N1···Cl1i | 0.844 (17) | 2.529 (18) | 3.3437 (17) | 163 (2) |
N2—H1N2···Cl2 | 0.838 (18) | 2.78 (3) | 3.2013 (18) | 113.1 (19) |
N2—H1N2···Cl1ii | 0.841 (18) | 2.594 (17) | 3.4014 (17) | 161 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z. |
(C6H16N)2[Sn(CH3)2Cl4] | F(000) = 1016 |
Mr = 494.95 | Dx = 1.347 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9199 (3) Å | Cell parameters from 7502 reflections |
b = 13.1459 (3) Å | θ = 1.9–28.7° |
c = 17.8167 (5) Å | µ = 1.48 mm−1 |
β = 107.328 (3)° | T = 120 K |
V = 2441.54 (12) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.15 × 0.10 mm |
AFC11 (Right): Eulerian 3 circle CCD diffractometer | 3764 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.040 |
Profile data from ω–scans | θmax = 25.4°, θmin = 3.0° |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011) | h = −12→13 |
Tmin = 0.849, Tmax = 1.000 | k = −15→15 |
15263 measured reflections | l = −21→21 |
4469 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0278P)2 + 1.1521P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
4469 reflections | Δρmax = 0.76 e Å−3 |
208 parameters | Δρmin = −0.42 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The structure of (I) was refined with program Jana2006 (Petříček et al., 2014), the structure (II) was refined using SHELXL2018/3 (Sheldrick, 2015b), and the refinement parameters are summarized in Table 1. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.52874 (2) | 0.06248 (2) | 0.80343 (2) | 0.02455 (8) | |
Cl1 | 0.74733 (7) | 0.14311 (6) | 0.81057 (6) | 0.0379 (2) | |
Cl2 | 0.30570 (7) | −0.01909 (6) | 0.78896 (6) | 0.0374 (2) | |
Cl3 | 0.62060 (7) | −0.12127 (6) | 0.80438 (5) | 0.03311 (19) | |
Cl4 | 0.43741 (7) | 0.24724 (6) | 0.80492 (5) | 0.03046 (18) | |
C1 | 0.5721 (4) | 0.0596 (3) | 0.9266 (2) | 0.0432 (9) | |
H1A | 0.613622 | −0.005113 | 0.946752 | 0.065* | |
H1B | 0.492860 | 0.066629 | 0.941250 | 0.065* | |
H1C | 0.630187 | 0.115910 | 0.949289 | 0.065* | |
C2 | 0.4774 (3) | 0.0677 (2) | 0.67949 (19) | 0.0344 (8) | |
H2A | 0.474161 | −0.001608 | 0.658708 | 0.052* | |
H2B | 0.541259 | 0.107401 | 0.663367 | 0.052* | |
H2C | 0.392975 | 0.099703 | 0.658852 | 0.052* | |
N1 | 0.6384 (2) | 0.3863 (2) | 0.75907 (16) | 0.0261 (6) | |
H1N1 | 0.698 (3) | 0.377 (3) | 0.745 (2) | 0.031* | |
H1N2 | 0.615 (3) | 0.327 (3) | 0.7726 (19) | 0.031* | |
C3 | 0.8191 (4) | 0.4699 (4) | 0.9683 (2) | 0.0625 (12) | |
H3A | 0.881580 | 0.434195 | 1.011299 | 0.094* | |
H3B | 0.744170 | 0.488452 | 0.984887 | 0.094* | |
H3C | 0.858446 | 0.531577 | 0.954904 | 0.094* | |
C4 | 0.7773 (3) | 0.4004 (3) | 0.8964 (2) | 0.0418 (9) | |
H4A | 0.852159 | 0.384967 | 0.877849 | 0.050* | |
H4B | 0.744893 | 0.335464 | 0.911305 | 0.050* | |
C5 | 0.6739 (3) | 0.4497 (2) | 0.8310 (2) | 0.0330 (8) | |
H5A | 0.597103 | 0.460928 | 0.848583 | 0.040* | |
H5B | 0.704376 | 0.516791 | 0.818785 | 0.040* | |
C6 | 0.5339 (3) | 0.4304 (2) | 0.69333 (19) | 0.0299 (7) | |
H6A | 0.559663 | 0.498893 | 0.680553 | 0.036* | |
H6B | 0.455565 | 0.437921 | 0.710004 | 0.036* | |
C7 | 0.5046 (3) | 0.3643 (3) | 0.6212 (2) | 0.0408 (9) | |
H7A | 0.480918 | 0.295279 | 0.634239 | 0.049* | |
H7B | 0.582166 | 0.358287 | 0.603600 | 0.049* | |
C8 | 0.3962 (4) | 0.4079 (4) | 0.5554 (2) | 0.0560 (11) | |
H8A | 0.379907 | 0.363777 | 0.509063 | 0.084* | |
H8B | 0.419696 | 0.476036 | 0.542121 | 0.084* | |
H8C | 0.318672 | 0.412092 | 0.572138 | 0.084* | |
N2 | 0.1338 (3) | 0.2421 (2) | 0.74957 (17) | 0.0293 (6) | |
H2N1 | 0.214 (3) | 0.248 (3) | 0.759 (2) | 0.035* | |
H2N2 | 0.101 (3) | 0.301 (3) | 0.735 (2) | 0.035* | |
C9 | 0.1422 (5) | 0.2318 (3) | 0.9650 (2) | 0.0621 (12) | |
H9A | 0.179875 | 0.277668 | 1.009211 | 0.093* | |
H9B | 0.182825 | 0.164772 | 0.976190 | 0.093* | |
H9C | 0.049909 | 0.225237 | 0.957394 | 0.093* | |
C10 | 0.1640 (4) | 0.2749 (3) | 0.8907 (2) | 0.0418 (9) | |
H10A | 0.122963 | 0.342604 | 0.879310 | 0.050* | |
H10B | 0.257106 | 0.283374 | 0.898817 | 0.050* | |
C11 | 0.1083 (3) | 0.2047 (2) | 0.8220 (2) | 0.0321 (8) | |
H11A | 0.146117 | 0.136081 | 0.834785 | 0.039* | |
H11B | 0.014566 | 0.198938 | 0.812544 | 0.039* | |
C12 | 0.0760 (3) | 0.1783 (2) | 0.67894 (19) | 0.0312 (7) | |
H12A | −0.017756 | 0.173597 | 0.670164 | 0.037* | |
H12B | 0.111861 | 0.108748 | 0.688630 | 0.037* | |
C13 | 0.1005 (3) | 0.2205 (3) | 0.6060 (2) | 0.0401 (9) | |
H13A | 0.193952 | 0.222128 | 0.613334 | 0.048* | |
H13B | 0.067677 | 0.291109 | 0.597068 | 0.048* | |
C14 | 0.0344 (4) | 0.1552 (3) | 0.5348 (2) | 0.0604 (12) | |
H14A | 0.052822 | 0.182565 | 0.488112 | 0.091* | |
H14B | −0.058449 | 0.155751 | 0.526435 | 0.091* | |
H14C | 0.066349 | 0.085217 | 0.543930 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02077 (12) | 0.02605 (12) | 0.02775 (13) | −0.00016 (9) | 0.00863 (9) | 0.00115 (9) |
Cl1 | 0.0242 (4) | 0.0301 (4) | 0.0634 (6) | −0.0017 (3) | 0.0192 (4) | −0.0014 (4) |
Cl2 | 0.0211 (4) | 0.0306 (4) | 0.0616 (6) | 0.0000 (3) | 0.0141 (4) | −0.0003 (4) |
Cl3 | 0.0223 (4) | 0.0259 (4) | 0.0544 (6) | 0.0015 (3) | 0.0164 (4) | 0.0052 (4) |
Cl4 | 0.0234 (4) | 0.0263 (4) | 0.0446 (5) | 0.0001 (3) | 0.0145 (4) | −0.0019 (3) |
C1 | 0.040 (2) | 0.056 (2) | 0.030 (2) | −0.0008 (18) | 0.0042 (16) | 0.0051 (17) |
C2 | 0.046 (2) | 0.0318 (18) | 0.0260 (19) | 0.0050 (15) | 0.0118 (16) | 0.0010 (14) |
N1 | 0.0207 (13) | 0.0259 (14) | 0.0337 (17) | −0.0018 (12) | 0.0109 (12) | −0.0026 (12) |
C3 | 0.058 (3) | 0.090 (3) | 0.037 (2) | −0.017 (3) | 0.010 (2) | −0.016 (2) |
C4 | 0.0353 (19) | 0.055 (2) | 0.034 (2) | −0.0045 (18) | 0.0080 (17) | −0.0044 (18) |
C5 | 0.0304 (17) | 0.0345 (18) | 0.037 (2) | −0.0072 (15) | 0.0136 (15) | −0.0085 (15) |
C6 | 0.0218 (15) | 0.0301 (17) | 0.037 (2) | 0.0016 (14) | 0.0072 (14) | 0.0040 (15) |
C7 | 0.0311 (18) | 0.050 (2) | 0.041 (2) | 0.0024 (17) | 0.0099 (17) | −0.0028 (17) |
C8 | 0.038 (2) | 0.093 (3) | 0.034 (2) | 0.012 (2) | 0.0069 (18) | 0.002 (2) |
N2 | 0.0196 (13) | 0.0281 (15) | 0.0406 (18) | −0.0009 (12) | 0.0097 (13) | 0.0029 (13) |
C9 | 0.083 (3) | 0.064 (3) | 0.048 (3) | −0.001 (3) | 0.033 (2) | 0.001 (2) |
C10 | 0.046 (2) | 0.044 (2) | 0.040 (2) | −0.0036 (18) | 0.0206 (18) | −0.0020 (17) |
C11 | 0.0268 (16) | 0.0306 (17) | 0.043 (2) | 0.0013 (14) | 0.0175 (15) | 0.0086 (15) |
C12 | 0.0244 (15) | 0.0280 (17) | 0.039 (2) | 0.0019 (14) | 0.0061 (14) | −0.0035 (15) |
C13 | 0.0390 (19) | 0.041 (2) | 0.040 (2) | 0.0033 (17) | 0.0112 (17) | −0.0012 (16) |
C14 | 0.069 (3) | 0.067 (3) | 0.041 (3) | −0.002 (2) | 0.010 (2) | −0.009 (2) |
Sn1—C1 | 2.104 (3) | C4—C5 | 1.506 (5) |
Sn1—C2 | 2.111 (3) | C6—C7 | 1.505 (5) |
Sn1—Cl1 | 2.5799 (8) | C7—C8 | 1.509 (5) |
Sn1—Cl2 | 2.6028 (8) | N2—C11 | 1.482 (4) |
Sn1—Cl3 | 2.6136 (8) | N2—C12 | 1.487 (4) |
Sn1—Cl4 | 2.6288 (8) | C9—C10 | 1.522 (5) |
N1—C5 | 1.480 (4) | C10—C11 | 1.509 (5) |
N1—C6 | 1.488 (4) | C12—C13 | 1.508 (5) |
C3—C4 | 1.528 (5) | C13—C14 | 1.525 (5) |
C1—Sn1—C2 | 177.59 (13) | Cl2—Sn1—Cl4 | 92.01 (2) |
C1—Sn1—Cl1 | 92.19 (11) | Cl3—Sn1—Cl4 | 179.09 (3) |
C2—Sn1—Cl1 | 89.53 (10) | C5—N1—C6 | 113.8 (3) |
C1—Sn1—Cl2 | 90.53 (11) | C5—C4—C3 | 111.1 (3) |
C2—Sn1—Cl2 | 87.75 (10) | N1—C5—C4 | 111.8 (3) |
Cl1—Sn1—Cl2 | 177.27 (3) | N1—C6—C7 | 111.4 (3) |
C1—Sn1—Cl3 | 90.56 (11) | C6—C7—C8 | 111.3 (3) |
C2—Sn1—Cl3 | 91.07 (9) | C11—N2—C12 | 114.0 (3) |
Cl1—Sn1—Cl3 | 91.82 (2) | C11—C10—C9 | 110.4 (3) |
Cl2—Sn1—Cl3 | 88.05 (2) | N2—C11—C10 | 111.7 (3) |
C1—Sn1—Cl4 | 88.53 (11) | N2—C12—C13 | 112.4 (3) |
C2—Sn1—Cl4 | 89.84 (9) | C12—C13—C14 | 110.4 (3) |
Cl1—Sn1—Cl4 | 88.17 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···Cl3i | 0.77 (3) | 2.40 (3) | 3.160 (3) | 170 (3) |
N1—H1N2···Cl1 | 0.87 (3) | 2.80 (3) | 3.439 (3) | 132 (3) |
N1—H1N2···Cl4 | 0.87 (3) | 2.42 (3) | 3.145 (3) | 141 (3) |
N2—H2N1···Cl4 | 0.84 (3) | 2.33 (4) | 3.166 (3) | 170 (3) |
N2—H2N2···Cl2ii | 0.86 (4) | 2.66 (3) | 3.321 (3) | 135 (3) |
N2—H2N2···Cl3ii | 0.86 (4) | 2.53 (4) | 3.205 (3) | 136 (3) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2. |