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The conformational flexibilities are studied in two new organotin(IV) complexes, namely,
trans-dichloridodimethylbis[
N,
N′,
N′′-tris(2-chlorobenzyl)phosphoric triamide]tin(IV), [Sn(CH
3)
2(C
21H
21Cl
3N
3OP)
2Cl
2] or Sn(CH
3)
2Cl
2{OP[NHCH
2C
6H
4(2-Cl)]
3}
2, (I), and bis(dipropylammonium) tetrachloridodimethylstannate(IV), [(CH
3CH
2CH
2)
2NH
2]
2[Sn(CH
3)
2Cl
4], (II), and their analogous structures from the Cambridge Structural Database (CSD). The conformations are considered based on the N—P=O—Sn torsion angles for (I) and the C—C—C—N, C—C—N—C, C—N—C—C and N—C—C—C torsion angles for the two symmetry-independent [CH
3CH
2CH
2NH
2CH
2CH
2CH
3]
+ cations in (II), and the ±ac±sp±ac (ac = anticlinal and sp = synperiplanar) and ±ap±ap±ap±ap (ap = antiperiplanar) conformations are observed, respectively. In both structures, the four atoms in the corners of the square-planar segment of the octahedral shape around the Sn atom participate in normal hydrogen-bonding interactions as acceptors, which include two O and two Cl atoms for (I), and four Cl atoms for (II). However, the phosphoric triamide ligands block the environment around the Sn atom and limit the hydrogen-bond pattern to form a supramolecular ribbon assembly, while in the presence of small organic cations in (II), a two-dimensional hydrogen-bonded architecture is achieved. The weak interactions π–π, C—H
π and C—Cl
π in (I), and C—H
Cl in (II) do not change the dimensionality of the hydrogen-bond pattern. The 62 CSD structures analogous to (I),
i.e. with an SnOPN
3 segment (including 83 entries) fall into four categories of conformations based on the N—P=O—Sn torsion angles. The 132 [(CH
3CH
2CH
2)
2NH
2]
+ cations from 85 CSD structures are classified into seven groups based on the torsion angles noted for (II). Most of the CSD structures adopt the same associated conformations noted for (I) and (II). 15 [Sn(CH
3)
2Cl
4]
2− anions extracted from the CSD are compared with the structure of (II).
Supporting information
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).
trans-Dichloridodimethylbis[
N,
N',
N''-tris(2-chlorobenzyl)phosphoric triamide]tin(IV) (I)
top
Crystal data top
[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 | |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
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. |
Bis(dipropylammonium) tetrachloridodimethylstannate(IV) (II)
top
Crystal data top
(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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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. |
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