metal-organic compounds
In the title compound, [SnCl2(C19H22N2O)]·CHCl3, the deprotonated N-(2-aminocyclohexyl)salicylaldimine Schiff base chelates in an O,N,N′-tridentate manner to the Sn atom. The octahedral tin coordination environment is completed by a phenyl ring and two chloride ions; the bonded C atom of the phenyl ring along with the three chelating atoms comprise an approximate square plane. The molecules of the complex are linked by N—HO and N—HCl hydrogen bonds to form a helical chain running along the b axis; the solvent molecules occupy the space between the chains but are not hydrogen bonded to them.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025036/hb6204sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025036/hb6204Isup2.hkl |
CCDC reference: 255419
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[SnCl2(C19H22N2O)]·CHCl3 | F(000) = 1200 |
Mr = 603.34 | Dx = 1.640 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 967 reflections |
a = 11.877 (1) Å | θ = 2.4–28.3° |
b = 11.559 (1) Å | µ = 1.61 mm−1 |
c = 18.766 (2) Å | T = 223 K |
β = 108.449 (2)° | Block, colorless |
V = 2443.9 (4) Å3 | 0.40 × 0.36 × 0.24 mm |
Z = 4 |
Data collection top
Bruker SMART CCD diffractometer | 5614 independent reflections |
Radiation source: medium-focus sealed tube | 4850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→15 |
Tmin = 0.545, Tmax = 0.678 | k = −14→15 |
16789 measured reflections | l = −24→16 |
Refinement top
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0648P)2 + 3.2538P] where P = (Fo2 + 2Fc2)/3 |
5614 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 1.31 e Å−3 |
0 restraints | Δρmin = −0.72 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.34057 (2) | 0.46627 (2) | 0.28778 (1) | 0.0312 (1) | |
Cl1 | 0.52697 (9) | 0.55029 (9) | 0.37183 (5) | 0.0476 (2) | |
Cl2 | 0.14078 (8) | 0.38936 (8) | 0.21909 (5) | 0.0434 (2) | |
Cl3 | 0.6614 (4) | 0.8219 (3) | 0.2025 (2) | 0.193 (2) | |
Cl4 | 0.7778 (2) | 0.6333 (3) | 0.2861 (2) | 0.146 (1) | |
Cl5 | 0.7091 (3) | 0.8252 (3) | 0.3605 (2) | 0.171 (1) | |
O1 | 0.4111 (2) | 0.3030 (2) | 0.3018 (1) | 0.0407 (6) | |
N1 | 0.2982 (3) | 0.4312 (3) | 0.3910 (2) | 0.0396 (7) | |
N2 | 0.2503 (3) | 0.6286 (2) | 0.3063 (2) | 0.0384 (6) | |
C1 | 0.3811 (3) | 0.5165 (3) | 0.1895 (2) | 0.035 (1) | |
C2 | 0.2955 (4) | 0.5717 (3) | 0.1303 (2) | 0.043 (1) | |
C3 | 0.3232 (4) | 0.6056 (4) | 0.0668 (2) | 0.052 (1) | |
C4 | 0.4343 (5) | 0.5855 (4) | 0.0621 (2) | 0.058 (1) | |
C5 | 0.5195 (4) | 0.5310 (4) | 0.1198 (3) | 0.058 (1) | |
C6 | 0.4931 (4) | 0.4962 (4) | 0.1837 (2) | 0.046 (1) | |
C7 | 0.4664 (3) | 0.2514 (3) | 0.3673 (2) | 0.037 (1) | |
C8 | 0.5506 (4) | 0.1667 (3) | 0.3686 (3) | 0.051 (1) | |
C9 | 0.6063 (4) | 0.1060 (4) | 0.4341 (3) | 0.064 (1) | |
C10 | 0.5796 (4) | 0.1268 (4) | 0.4993 (3) | 0.058 (1) | |
C11 | 0.4970 (4) | 0.2094 (3) | 0.4992 (2) | 0.045 (1) | |
C12 | 0.4400 (3) | 0.2739 (3) | 0.4343 (2) | 0.036 (1) | |
C13 | 0.3532 (4) | 0.3575 (3) | 0.4405 (2) | 0.040 (1) | |
C14 | 0.2082 (6) | 0.5127 (4) | 0.4029 (3) | 0.069 (2) | |
C15 | 0.1846 (4) | 0.5052 (4) | 0.4760 (2) | 0.047 (1) | |
C16 | 0.0996 (6) | 0.6013 (5) | 0.4832 (4) | 0.089 (2) | |
C17 | 0.1178 (9) | 0.7110 (6) | 0.4582 (4) | 0.132 (4) | |
C18 | 0.1436 (5) | 0.7188 (4) | 0.3861 (3) | 0.062 (1) | |
C19 | 0.2289 (6) | 0.6259 (4) | 0.3777 (3) | 0.079 (2) | |
C20 | 0.6741 (5) | 0.7421 (6) | 0.2808 (3) | 0.083 (2) | |
H2n1 | 0.2966 | 0.6908 | 0.3048 | 0.046* | |
H2n2 | 0.1801 | 0.6367 | 0.2689 | 0.046* | |
H2 | 0.2193 | 0.5857 | 0.1335 | 0.051* | |
H3 | 0.2656 | 0.6424 | 0.0269 | 0.062* | |
H4 | 0.4527 | 0.6092 | 0.0191 | 0.070* | |
H5 | 0.5954 | 0.5172 | 0.1159 | 0.070* | |
H6 | 0.5511 | 0.4590 | 0.2231 | 0.056* | |
H8 | 0.5698 | 0.1506 | 0.3247 | 0.061* | |
H9 | 0.6633 | 0.0497 | 0.4340 | 0.076* | |
H10 | 0.6177 | 0.0848 | 0.5432 | 0.069* | |
H11 | 0.4781 | 0.2233 | 0.5434 | 0.054* | |
H13 | 0.3352 | 0.3576 | 0.4858 | 0.048* | |
H14 | 0.1327 | 0.4879 | 0.3656 | 0.083* | |
H15a | 0.2596 | 0.5119 | 0.5172 | 0.056* | |
H15b | 0.1498 | 0.4296 | 0.4801 | 0.056* | |
H16a | 0.0185 | 0.5772 | 0.4553 | 0.107* | |
H16b | 0.1046 | 0.6074 | 0.5362 | 0.107* | |
H17a | 0.1839 | 0.7470 | 0.4972 | 0.158* | |
H17b | 0.0468 | 0.7575 | 0.4537 | 0.158* | |
H18a | 0.1776 | 0.7950 | 0.3826 | 0.074* | |
H18b | 0.0691 | 0.7121 | 0.3446 | 0.074* | |
H19 | 0.3060 | 0.6491 | 0.4140 | 0.095* | |
H20 | 0.5965 | 0.7048 | 0.2745 | 0.100* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0356 (1) | 0.0313 (1) | 0.0264 (1) | 0.00193 (8) | 0.0096 (1) | 0.00093 (8) |
Cl1 | 0.0408 (5) | 0.0611 (6) | 0.0373 (5) | −0.0073 (4) | 0.0072 (4) | −0.0089 (4) |
Cl2 | 0.0403 (4) | 0.0433 (5) | 0.0431 (5) | −0.0039 (4) | 0.0081 (4) | −0.0050 (4) |
Cl3 | 0.324 (5) | 0.148 (2) | 0.120 (2) | −0.064 (3) | 0.092 (3) | 0.017 (2) |
Cl4 | 0.097 (1) | 0.188 (3) | 0.166 (2) | −0.012 (2) | 0.060 (2) | −0.029 (2) |
Cl5 | 0.214 (3) | 0.196 (3) | 0.140 (2) | −0.128 (2) | 0.107 (2) | −0.107 (2) |
O1 | 0.051 (2) | 0.040 (1) | 0.029 (1) | 0.013 (1) | 0.010 (1) | −0.001 (1) |
N1 | 0.055 (2) | 0.033 (1) | 0.037 (2) | 0.008 (1) | 0.022 (2) | 0.006 (1) |
N2 | 0.046 (2) | 0.032 (1) | 0.039 (2) | 0.004 (1) | 0.017 (1) | 0.006 (1) |
C1 | 0.042 (2) | 0.032 (2) | 0.030 (2) | −0.001 (1) | 0.012 (2) | −0.002 (1) |
C2 | 0.051 (2) | 0.042 (2) | 0.037 (2) | 0.006 (2) | 0.016 (2) | 0.003 (2) |
C3 | 0.070 (3) | 0.052 (2) | 0.036 (2) | 0.009 (2) | 0.020 (2) | 0.009 (2) |
C4 | 0.084 (3) | 0.058 (3) | 0.045 (2) | −0.008 (2) | 0.039 (2) | 0.003 (2) |
C5 | 0.052 (3) | 0.078 (3) | 0.053 (3) | −0.004 (2) | 0.029 (2) | −0.008 (2) |
C6 | 0.044 (2) | 0.058 (2) | 0.038 (2) | 0.000 (2) | 0.015 (2) | −0.003 (2) |
C7 | 0.040 (2) | 0.029 (2) | 0.036 (2) | −0.001 (1) | 0.005 (1) | −0.002 (1) |
C8 | 0.056 (2) | 0.044 (2) | 0.049 (2) | 0.013 (2) | 0.014 (2) | −0.002 (2) |
C9 | 0.063 (3) | 0.051 (2) | 0.069 (3) | 0.025 (2) | 0.009 (2) | 0.007 (2) |
C10 | 0.068 (3) | 0.044 (2) | 0.049 (2) | 0.010 (2) | 0.002 (2) | 0.012 (2) |
C11 | 0.055 (2) | 0.036 (2) | 0.036 (2) | −0.002 (2) | 0.004 (2) | 0.004 (2) |
C12 | 0.042 (2) | 0.028 (2) | 0.032 (2) | −0.003 (1) | 0.004 (1) | 0.000 (1) |
C13 | 0.059 (2) | 0.032 (2) | 0.032 (2) | −0.001 (2) | 0.018 (2) | 0.002 (1) |
C14 | 0.101 (4) | 0.054 (3) | 0.078 (4) | 0.032 (3) | 0.064 (3) | 0.025 (2) |
C15 | 0.053 (2) | 0.051 (2) | 0.042 (2) | 0.006 (2) | 0.024 (2) | 0.007 (2) |
C16 | 0.124 (5) | 0.068 (3) | 0.116 (5) | 0.019 (3) | 0.096 (4) | 0.008 (3) |
C17 | 0.218 (9) | 0.105 (5) | 0.124 (6) | 0.097 (6) | 0.127 (7) | 0.047 (5) |
C18 | 0.089 (3) | 0.043 (2) | 0.067 (3) | 0.028 (2) | 0.044 (3) | 0.010 (2) |
C19 | 0.132 (5) | 0.059 (3) | 0.072 (3) | 0.050 (3) | 0.070 (3) | 0.027 (2) |
C20 | 0.081 (4) | 0.098 (4) | 0.081 (4) | −0.031 (3) | 0.040 (3) | −0.022 (3) |
Geometric parameters (Å, º) top
Sn1—Cl1 | 2.474 (1) | C15—C16 | 1.536 (7) |
Sn1—Cl2 | 2.479 (1) | C16—C17 | 1.392 (9) |
Sn1—O1 | 2.048 (2) | C17—C18 | 1.482 (7) |
Sn1—C1 | 2.129 (4) | C18—C19 | 1.519 (6) |
Sn1—N1 | 2.188 (3) | N2—H2n1 | 0.91 |
Sn1—N2 | 2.243 (3) | N2—H2n2 | 0.91 |
Cl3—C20 | 1.701 (7) | C2—H2 | 0.94 |
Cl4—C20 | 1.741 (7) | C3—H3 | 0.94 |
Cl5—C20 | 1.715 (6) | C4—H4 | 0.94 |
O1—C7 | 1.337 (4) | C5—H5 | 0.94 |
N1—C13 | 1.278 (5) | C6—H6 | 0.94 |
N1—C14 | 1.494 (5) | C8—H8 | 0.94 |
N2—C19 | 1.440 (5) | C9—H9 | 0.94 |
C1—C6 | 1.388 (5) | C10—H10 | 0.94 |
C1—C2 | 1.400 (5) | C11—H11 | 0.94 |
C2—C3 | 1.390 (5) | C13—H13 | 0.94 |
C3—C4 | 1.370 (7) | C14—H14 | 0.99 |
C4—C5 | 1.379 (7) | C15—H15a | 0.98 |
C5—C6 | 1.392 (6) | C15—H15b | 0.98 |
C7—C8 | 1.394 (5) | C16—H16a | 0.98 |
C7—C12 | 1.413 (5) | C16—H16b | 0.98 |
C8—C9 | 1.388 (6) | C17—H17a | 0.98 |
C9—C10 | 1.378 (7) | C17—H17b | 0.98 |
C10—C11 | 1.368 (6) | C18—H18a | 0.98 |
C11—C12 | 1.406 (5) | C18—H18b | 0.98 |
C12—C13 | 1.444 (5) | C19—H19 | 0.99 |
C14—C19 | 1.438 (7) | C20—H20 | 0.99 |
C14—C15 | 1.487 (6) | ||
Cl1—Sn1—Cl2 | 171.21 (3) | Cl5—C20—Cl4 | 112.5 (4) |
Cl1—Sn1—O1 | 91.9 (1) | C19—N2—H2n1 | 109.4 |
Cl1—Sn1—C1 | 92.5 (1) | Sn1—N2—H2n1 | 109.4 |
Cl1—Sn1—N1 | 85.3 (1) | C19—N2—H2n2 | 109.4 |
Cl1—Sn1—N2 | 87.0 (1) | Sn1—N2—H2n2 | 109.4 |
Cl2—Sn1—O1 | 91.2 (1) | H2n1—N2—H2n2 | 108.0 |
Cl2—Sn1—N1 | 86.8 (1) | C3—C2—H2 | 120.0 |
Cl2—Sn1—N2 | 87.4 (1) | C1—C2—H2 | 120.0 |
Cl2—Sn1—C1 | 95.1 (1) | C4—C3—H3 | 119.9 |
O1—Sn1—N1 | 85.1 (1) | C2—C3—H3 | 119.9 |
O1—Sn1—N2 | 161.4 (1) | C3—C4—H4 | 119.7 |
O1—Sn1—C1 | 99.7 (1) | C5—C4—H4 | 119.7 |
N1—Sn1—N2 | 76.3 (1) | C4—C5—H5 | 120.0 |
N1—Sn1—C1 | 174.8 (1) | C6—C5—H5 | 120.0 |
N2—Sn1—C1 | 99.0 (1) | C1—C6—H6 | 120.0 |
C7—O1—Sn1 | 126.2 (2) | C5—C6—H6 | 120.0 |
C13—N1—C14 | 122.5 (3) | C9—C8—H8 | 119.7 |
C13—N1—Sn1 | 124.0 (3) | C7—C8—H8 | 119.7 |
C14—N1—Sn1 | 113.0 (2) | C10—C9—H9 | 119.4 |
C19—N2—Sn1 | 111.1 (2) | C8—C9—H9 | 119.4 |
C6—C1—C2 | 119.3 (4) | C10—C11—H11 | 119.3 |
C6—C1—Sn1 | 120.4 (3) | C12—C11—H11 | 119.3 |
C2—C1—Sn1 | 120.3 (3) | N1—C13—H13 | 116.5 |
C3—C2—C1 | 119.9 (4) | C12—C13—H13 | 116.5 |
C4—C3—C2 | 120.1 (4) | C19—C14—H14 | 104.0 |
C3—C4—C5 | 120.6 (4) | C15—C14—H14 | 104.0 |
C4—C5—C6 | 120.0 (4) | N1—C14—H14 | 104.0 |
C1—C6—C5 | 120.1 (4) | C14—C15—H15a | 109.4 |
O1—C7—C8 | 118.1 (3) | C16—C15—H15a | 109.4 |
O1—C7—C12 | 123.6 (3) | C14—C15—H15b | 109.4 |
C8—C7—C12 | 118.3 (3) | C16—C15—H15b | 109.4 |
C9—C8—C7 | 120.6 (4) | H15a—C15—H15b | 108.0 |
C10—C9—C8 | 121.3 (4) | C17—C16—H16a | 108.1 |
C11—C10—C9 | 119.1 (4) | C15—C16—H16a | 108.1 |
C11—C10—H10 | 120.5 | C17—C16—H16b | 108.1 |
C9—C10—H10 | 120.5 | C15—C16—H16b | 108.1 |
C10—C11—C12 | 121.3 (4) | H16a—C16—H16b | 107.3 |
C11—C12—C7 | 119.4 (3) | C16—C17—H17a | 107.9 |
C11—C12—C13 | 116.4 (3) | C18—C17—H17a | 107.9 |
C7—C12—C13 | 124.1 (3) | C16—C17—H17b | 107.9 |
N1—C13—C12 | 126.9 (3) | C18—C17—H17b | 107.9 |
C19—C14—C15 | 117.3 (5) | H17a—C17—H17b | 107.2 |
C19—C14—N1 | 108.6 (4) | C17—C18—H18a | 109.0 |
C15—C14—N1 | 117.0 (4) | C19—C18—H18a | 109.0 |
C14—C15—C16 | 111.1 (4) | C17—C18—H18b | 109.0 |
C17—C16—C15 | 116.9 (5) | C19—C18—H18b | 109.0 |
C16—C17—C18 | 117.5 (6) | H18a—C18—H18b | 107.8 |
C17—C18—C19 | 112.9 (4) | C14—C19—H19 | 103.8 |
C14—C19—N2 | 115.2 (4) | N2—C19—H19 | 103.8 |
C14—C19—C18 | 114.8 (5) | C18—C19—H19 | 103.8 |
N2—C19—C18 | 113.6 (4) | Cl3—C20—H20 | 107.9 |
Cl3—C20—Cl5 | 112.3 (4) | Cl5—C20—H20 | 107.9 |
Cl3—C20—Cl4 | 108.0 (4) | Cl4—C20—H20 | 107.9 |
C1—Sn1—O1—C7 | 143.5 (3) | Sn1—O1—C7—C8 | −152.9 (3) |
N1—Sn1—O1—C7 | −34.5 (3) | Sn1—O1—C7—C12 | 30.5 (5) |
N2—Sn1—O1—C7 | −35.5 (5) | O1—C7—C8—C9 | −176.6 (4) |
Cl1—Sn1—O1—C7 | 50.6 (3) | C12—C7—C8—C9 | 0.2 (6) |
Cl2—Sn1—O1—C7 | −121.1 (3) | C7—C8—C9—C10 | 0.5 (7) |
O1—Sn1—N1—C13 | 23.9 (3) | C8—C9—C10—C11 | −0.3 (7) |
N2—Sn1—N1—C13 | −156.4 (3) | C9—C10—C11—C12 | −0.6 (6) |
Cl1—Sn1—N1—C13 | −68.4 (3) | C10—C11—C12—C7 | 1.3 (5) |
Cl2—Sn1—N1—C13 | 115.4 (3) | C10—C11—C12—C13 | 179.1 (4) |
O1—Sn1—N1—C14 | −163.4 (4) | O1—C7—C12—C11 | 175.5 (3) |
N2—Sn1—N1—C14 | 16.3 (4) | C8—C7—C12—C11 | −1.1 (5) |
Cl1—Sn1—N1—C14 | 104.3 (4) | O1—C7—C12—C13 | −2.1 (5) |
Cl2—Sn1—N1—C14 | −71.8 (4) | C8—C7—C12—C13 | −178.7 (4) |
O1—Sn1—N2—C19 | 8.1 (6) | C14—N1—C13—C12 | 178.9 (4) |
C1—Sn1—N2—C19 | −170.9 (4) | Sn1—N1—C13—C12 | −9.0 (6) |
N1—Sn1—N2—C19 | 7.0 (4) | C11—C12—C13—N1 | 173.9 (4) |
Cl1—Sn1—N2—C19 | −78.9 (4) | C7—C12—C13—N1 | −8.4 (6) |
Cl2—Sn1—N2—C19 | 94.3 (4) | C13—N1—C14—C19 | 135.8 (5) |
O1—Sn1—C1—C6 | −45.7 (3) | Sn1—N1—C14—C19 | −37.1 (6) |
N2—Sn1—C1—C6 | 134.0 (3) | C13—N1—C14—C15 | 0.2 (8) |
Cl1—Sn1—C1—C6 | 46.6 (3) | Sn1—N1—C14—C15 | −172.7 (4) |
Cl2—Sn1—C1—C6 | −137.8 (3) | C19—C14—C15—C16 | 42.9 (8) |
O1—Sn1—C1—C2 | 135.0 (3) | N1—C14—C15—C16 | 174.6 (5) |
N2—Sn1—C1—C2 | −45.3 (3) | C14—C15—C16—C17 | −41.7 (9) |
Cl1—Sn1—C1—C2 | −132.7 (3) | C15—C16—C17—C18 | 43.2 (12) |
Cl2—Sn1—C1—C2 | 42.9 (3) | C16—C17—C18—C19 | −41.8 (11) |
C6—C1—C2—C3 | −0.2 (6) | C15—C14—C19—N2 | −179.5 (5) |
Sn1—C1—C2—C3 | 179.1 (3) | N1—C14—C19—N2 | 45.1 (7) |
C1—C2—C3—C4 | −0.2 (6) | C15—C14—C19—C18 | −44.7 (8) |
C2—C3—C4—C5 | 0.5 (7) | N1—C14—C19—C18 | 179.9 (5) |
C3—C4—C5—C6 | −0.3 (7) | Sn1—N2—C19—C14 | −31.2 (7) |
C2—C1—C6—C5 | 0.3 (6) | Sn1—N2—C19—C18 | −166.5 (4) |
Sn1—C1—C6—C5 | −179.0 (3) | C17—C18—C19—C14 | 41.6 (9) |
C4—C5—C6—C1 | 0.0 (7) | C17—C18—C19—N2 | 177.0 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n1···Cl2i | 0.91 | 2.50 | 3.372 (3) | 162 |
N2—H2n2···O1i | 0.91 | 2.39 | 3.065 (4) | 131 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |