metal-organic compounds
Redetermination of L-(–)-dichloro(N,N-diethyldithiocarbamato)(β-menthoxycarbonylethyl)tin(IV)
The crystal structure of the chiral title compound, [Sn(C5H10NS2)(C13H23O2)Cl2], has been determined in space group P212121. The Sn atom is in a distorted octahedral geometry within a CCl2OS2 donor set.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501281X/tk6223sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680501281X/tk6223Isup2.hkl |
CCDC reference: 274656
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: averaging the two molecules described in P21 (Lai et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Sn(C5H10NS2)(C13H23O2)Cl2] | F(000) = 1120 |
Mr = 549.16 | Dx = 1.440 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5645 reflections |
a = 10.305 (1) Å | θ = 2.6–24.7° |
b = 12.088 (1) Å | µ = 1.40 mm−1 |
c = 20.341 (2) Å | T = 295 K |
V = 2533.8 (4) Å3 | Irregular block, colorless |
Z = 4 | 0.27 × 0.12 × 0.09 mm |
Data collection top
Bruker APEX area-detector diffractometer | 5665 independent reflections |
Radiation source: fine-focus sealed tube | 5005 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→12 |
Tmin = 0.675, Tmax = 0.885 | k = −15→14 |
15820 measured reflections | l = −23→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
5665 reflections | Δρmax = 0.52 e Å−3 |
235 parameters | Δρmin = −0.63 e Å−3 |
0 restraints | Absolute structure: Flack parameter from 2417 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.17309 (2) | 0.60715 (2) | 0.91989 (1) | 0.04835 (8) | |
Cl1 | −0.0354 (1) | 0.6951 (1) | 0.91492 (6) | 0.0790 (4) | |
Cl2 | 0.1368 (1) | 0.5348 (1) | 1.02851 (5) | 0.0743 (3) | |
S1 | 0.1152 (1) | 0.42765 (8) | 0.87082 (4) | 0.0531 (2) | |
S2 | 0.2102 (1) | 0.61134 (8) | 0.78885 (4) | 0.0559 (2) | |
O1 | 0.3820 (3) | 0.5265 (2) | 0.9307 (2) | 0.0592 (7) | |
O2 | 0.5902 (3) | 0.5712 (2) | 0.9187 (2) | 0.0665 (7) | |
N1 | 0.1387 (3) | 0.4170 (2) | 0.7412 (1) | 0.0476 (7) | |
C1 | 0.1535 (3) | 0.4794 (3) | 0.7936 (2) | 0.042 (1) | |
C2 | 0.0906 (5) | 0.3015 (3) | 0.7450 (2) | 0.068 (1) | |
C3 | 0.1971 (6) | 0.2185 (4) | 0.7435 (3) | 0.100 (2) | |
C4 | 0.1707 (5) | 0.4560 (3) | 0.6743 (2) | 0.059 (1) | |
C5 | 0.0567 (5) | 0.5063 (4) | 0.6405 (2) | 0.080 (1) | |
C6 | 0.3003 (4) | 0.7448 (3) | 0.9329 (2) | 0.062 (1) | |
C7 | 0.4351 (4) | 0.7150 (3) | 0.9106 (2) | 0.065 (1) | |
C8 | 0.4669 (4) | 0.5955 (3) | 0.9212 (2) | 0.052 (1) | |
C9 | 0.6284 (4) | 0.4552 (3) | 0.9292 (2) | 0.062 (1) | |
C10 | 0.7034 (5) | 0.4506 (4) | 0.9926 (2) | 0.077 (1) | |
C11 | 0.7456 (5) | 0.3318 (4) | 1.0079 (3) | 0.084 (2) | |
C12 | 0.8224 (5) | 0.2860 (4) | 0.9492 (3) | 0.090 (2) | |
C13 | 0.7502 (6) | 0.2972 (4) | 0.8859 (3) | 0.087 (2) | |
C14 | 0.7082 (4) | 0.4176 (3) | 0.8709 (2) | 0.065 (1) | |
C15 | 0.8250 (7) | 0.3278 (6) | 1.0708 (3) | 0.123 (2) | |
C16 | 0.6414 (5) | 0.4335 (4) | 0.8039 (2) | 0.076 (1) | |
C17 | 0.7361 (6) | 0.4152 (4) | 0.7470 (3) | 0.106 (2) | |
C18 | 0.5197 (6) | 0.3659 (4) | 0.7937 (3) | 0.102 (2) | |
H2a | 0.0414 | 0.2925 | 0.7853 | 0.081* | |
H2b | 0.0324 | 0.2879 | 0.7084 | 0.081* | |
H3a | 0.1610 | 0.1454 | 0.7459 | 0.150* | |
H3b | 0.2538 | 0.2302 | 0.7803 | 0.150* | |
H3c | 0.2454 | 0.2262 | 0.7034 | 0.150* | |
H4a | 0.2021 | 0.3941 | 0.6484 | 0.071* | |
H4b | 0.2398 | 0.5103 | 0.6769 | 0.071* | |
H5a | 0.0816 | 0.5301 | 0.5973 | 0.120* | |
H5b | 0.0264 | 0.5686 | 0.6654 | 0.120* | |
H5c | −0.0115 | 0.4524 | 0.6371 | 0.120* | |
H6a | 0.2688 | 0.8074 | 0.9077 | 0.075* | |
H6b | 0.3020 | 0.7660 | 0.9789 | 0.075* | |
H7a | 0.4436 | 0.7321 | 0.8643 | 0.078* | |
H7b | 0.4973 | 0.7600 | 0.9344 | 0.078* | |
H9a | 0.5505 | 0.4091 | 0.9329 | 0.074* | |
H10a | 0.6497 | 0.4782 | 1.0282 | 0.092* | |
H10b | 0.7794 | 0.4976 | 0.9893 | 0.092* | |
H11 | 0.6677 | 0.2864 | 1.0139 | 0.101* | |
H12a | 0.9043 | 0.3252 | 0.9459 | 0.107* | |
H12b | 0.8416 | 0.2085 | 0.9569 | 0.107* | |
H13a | 0.6736 | 0.2506 | 0.8875 | 0.105* | |
H13b | 0.8047 | 0.2707 | 0.8503 | 0.105* | |
H14 | 0.7872 | 0.4627 | 0.8703 | 0.077* | |
H15a | 0.8510 | 0.2529 | 1.0794 | 0.185* | |
H15b | 0.7734 | 0.3545 | 1.1068 | 0.185* | |
H15c | 0.9006 | 0.3734 | 1.0660 | 0.185* | |
H16 | 0.6150 | 0.5113 | 0.8018 | 0.091* | |
H17a | 0.6914 | 0.4251 | 0.7060 | 0.159* | |
H17b | 0.7704 | 0.3414 | 0.7492 | 0.159* | |
H17c | 0.8059 | 0.4675 | 0.7500 | 0.159* | |
H18a | 0.4611 | 0.3781 | 0.8297 | 0.153* | |
H18b | 0.5418 | 0.2888 | 0.7916 | 0.153* | |
H18c | 0.4788 | 0.3877 | 0.7533 | 0.153* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0547 (1) | 0.0534 (1) | 0.0370 (1) | 0.0130 (1) | −0.0051 (1) | −0.0067 (1) |
Cl1 | 0.0731 (7) | 0.1109 (9) | 0.0532 (6) | 0.0450 (7) | 0.0044 (6) | 0.0135 (7) |
Cl2 | 0.0935 (9) | 0.0908 (8) | 0.0387 (5) | 0.0229 (7) | −0.0050 (5) | 0.0052 (5) |
S1 | 0.0627 (6) | 0.0578 (6) | 0.0389 (5) | −0.0100 (5) | 0.0045 (4) | 0.0016 (4) |
S2 | 0.0809 (7) | 0.0443 (4) | 0.0426 (5) | −0.0103 (5) | 0.0046 (4) | −0.0040 (4) |
O1 | 0.048 (1) | 0.047 (1) | 0.082 (2) | 0.001 (1) | −0.002 (1) | −0.001 (1) |
O2 | 0.052 (2) | 0.050 (1) | 0.098 (2) | −0.003 (1) | 0.014 (2) | −0.007 (2) |
N1 | 0.058 (2) | 0.045 (2) | 0.039 (2) | −0.010 (1) | 0.004 (1) | −0.005 (1) |
C1 | 0.041 (2) | 0.048 (2) | 0.039 (2) | −0.001 (2) | 0.001 (1) | −0.003 (1) |
C2 | 0.090 (3) | 0.059 (3) | 0.055 (2) | −0.025 (2) | −0.002 (2) | −0.010 (2) |
C3 | 0.132 (6) | 0.059 (3) | 0.110 (4) | 0.017 (3) | −0.033 (4) | −0.007 (3) |
C4 | 0.078 (3) | 0.062 (2) | 0.037 (2) | −0.007 (2) | 0.009 (2) | −0.004 (2) |
C5 | 0.099 (4) | 0.086 (3) | 0.055 (3) | 0.001 (3) | −0.005 (3) | 0.011 (2) |
C6 | 0.084 (3) | 0.041 (2) | 0.062 (2) | 0.012 (2) | −0.020 (2) | −0.019 (2) |
C7 | 0.079 (3) | 0.043 (2) | 0.074 (3) | −0.005 (2) | −0.010 (3) | −0.012 (2) |
C8 | 0.055 (2) | 0.049 (2) | 0.053 (2) | 0.005 (2) | 0.000 (2) | −0.012 (2) |
C9 | 0.050 (2) | 0.047 (2) | 0.088 (3) | 0.000 (2) | 0.017 (2) | −0.001 (2) |
C10 | 0.077 (4) | 0.078 (3) | 0.076 (3) | 0.000 (3) | 0.020 (3) | −0.001 (2) |
C11 | 0.070 (3) | 0.079 (3) | 0.104 (4) | −0.002 (3) | 0.020 (3) | 0.024 (3) |
C12 | 0.074 (3) | 0.079 (3) | 0.116 (4) | 0.017 (3) | 0.022 (3) | 0.024 (3) |
C13 | 0.085 (4) | 0.064 (3) | 0.113 (4) | 0.017 (3) | 0.028 (3) | 0.001 (3) |
C14 | 0.052 (2) | 0.055 (2) | 0.086 (3) | 0.002 (2) | 0.016 (2) | −0.002 (2) |
C15 | 0.120 (5) | 0.141 (5) | 0.108 (5) | 0.002 (5) | −0.003 (5) | 0.043 (4) |
C16 | 0.089 (4) | 0.053 (2) | 0.086 (3) | 0.002 (2) | 0.012 (3) | −0.007 (2) |
C17 | 0.156 (6) | 0.063 (3) | 0.098 (4) | 0.002 (3) | 0.038 (4) | −0.007 (3) |
C18 | 0.104 (4) | 0.101 (4) | 0.101 (4) | −0.012 (4) | −0.006 (3) | −0.019 (3) |
Geometric parameters (Å, º) top
Sn1—C6 | 2.135 (4) | C3—H3b | 0.96 |
Sn1—O1 | 2.374 (3) | C3—H3c | 0.96 |
Sn1—S1 | 2.462 (1) | C4—H4a | 0.97 |
Sn1—S2 | 2.693 (1) | C4—H4b | 0.97 |
Sn1—Cl1 | 2.399 (1) | C5—H5a | 0.96 |
Sn1—Cl2 | 2.405 (1) | C5—H5b | 0.96 |
S1—C1 | 1.736 (3) | C5—H5c | 0.96 |
S2—C1 | 1.701 (3) | C6—H6a | 0.97 |
O1—C8 | 1.224 (4) | C6—H6b | 0.97 |
O2—C8 | 1.305 (5) | C7—H7a | 0.97 |
O2—C9 | 1.472 (5) | C7—H7b | 0.97 |
N1—C1 | 1.315 (4) | C9—H9a | 0.98 |
N1—C4 | 1.478 (4) | C10—H10a | 0.97 |
N1—C2 | 1.483 (5) | C10—H10b | 0.97 |
C2—C3 | 1.488 (7) | C11—H11 | 0.98 |
C4—C5 | 1.490 (6) | C12—H12a | 0.97 |
C6—C7 | 1.505 (6) | C12—H12b | 0.97 |
C7—C8 | 1.496 (5) | C13—H13a | 0.97 |
C9—C10 | 1.504 (6) | C13—H13b | 0.97 |
C9—C14 | 1.514 (6) | C14—H14 | 0.98 |
C10—C11 | 1.532 (7) | C15—H15a | 0.96 |
C11—C15 | 1.520 (7) | C15—H15b | 0.96 |
C11—C12 | 1.534 (7) | C15—H15c | 0.96 |
C12—C13 | 1.495 (7) | C16—H16 | 0.98 |
C13—C14 | 1.550 (6) | C17—H17a | 0.96 |
C14—C16 | 1.538 (7) | C17—H17b | 0.96 |
C16—C18 | 1.511 (7) | C17—H17c | 0.96 |
C16—C17 | 1.531 (7) | C18—H18a | 0.96 |
C2—H2a | 0.97 | C18—H18b | 0.96 |
C2—H2b | 0.97 | C18—H18c | 0.96 |
C3—H3a | 0.96 | ||
C6—Sn1—O1 | 75.6 (1) | H4a—C4—H4b | 107.9 |
C6—Sn1—S1 | 152.4 (1) | C4—C5—H5a | 109.5 |
C6—Sn1—S2 | 91.2 (1) | C4—C5—H5b | 109.5 |
C6—Sn1—Cl1 | 102.1 (1) | H5a—C5—H5b | 109.5 |
C6—Sn1—Cl2 | 105.3 (1) | C4—C5—H5c | 109.5 |
O1—Sn1—S1 | 84.02 (7) | H5a—C5—H5c | 109.5 |
O1—Sn1—S2 | 88.32 (8) | H5b—C5—H5c | 109.5 |
O1—Sn1—Cl1 | 176.49 (8) | C7—C6—H6a | 109.7 |
O1—Sn1—Cl2 | 84.63 (8) | Sn1—C6—H6a | 109.7 |
S1—Sn1—S2 | 69.50 (3) | C7—C6—H6b | 109.7 |
S1—Sn1—Cl1 | 98.98 (4) | Sn1—C6—H6b | 109.7 |
S1—Sn1—Cl2 | 90.83 (4) | H6a—C6—H6b | 108.2 |
S2—Sn1—Cl1 | 94.43 (4) | C8—C7—H7a | 109.0 |
S2—Sn1—Cl2 | 159.72 (4) | C6—C7—H7a | 109.0 |
Cl1—Sn1—Cl2 | 93.47 (4) | C8—C7—H7b | 109.0 |
C1—S1—Sn1 | 89.7 (1) | C6—C7—H7b | 109.0 |
C1—S2—Sn1 | 83.0 (1) | H7a—C7—H7b | 107.8 |
C8—O1—Sn1 | 110.7 (2) | O2—C9—H9a | 109.5 |
C8—O2—C9 | 118.0 (3) | C10—C9—H9a | 109.5 |
C1—N1—C4 | 122.6 (3) | C14—C9—H9a | 109.5 |
C1—N1—C2 | 122.4 (3) | C9—C10—H10a | 109.5 |
C4—N1—C2 | 115.0 (3) | C11—C10—H10a | 109.5 |
N1—C1—S2 | 122.1 (3) | C9—C10—H10b | 109.5 |
N1—C1—S1 | 120.0 (3) | C11—C10—H10b | 109.5 |
S2—C1—S1 | 117.9 (2) | H10a—C10—H10b | 108.1 |
C3—C2—N1 | 112.8 (4) | C15—C11—H11 | 108.5 |
N1—C4—C5 | 112.2 (4) | C10—C11—H11 | 108.5 |
C7—C6—Sn1 | 110.0 (2) | C12—C11—H11 | 108.5 |
C8—C7—C6 | 113.0 (4) | C13—C12—H12a | 109.1 |
O1—C8—O2 | 123.3 (3) | C11—C12—H12a | 109.1 |
O1—C8—C7 | 121.6 (3) | C13—C12—H12b | 109.1 |
O2—C8—C7 | 115.1 (4) | C11—C12—H12b | 109.1 |
O2—C9—C10 | 107.3 (3) | H12a—C12—H12b | 107.9 |
O2—C9—C14 | 108.5 (3) | C12—C13—H13a | 108.9 |
C10—C9—C14 | 112.5 (4) | C14—C13—H13a | 108.9 |
C9—C10—C11 | 110.8 (4) | C12—C13—H13b | 108.9 |
C15—C11—C10 | 110.7 (5) | C14—C13—H13b | 108.9 |
C15—C11—C12 | 111.5 (5) | H13a—C13—H13b | 107.8 |
C10—C11—C12 | 109.1 (4) | C9—C14—H14 | 107.0 |
C13—C12—C11 | 112.4 (4) | C16—C14—H14 | 107.0 |
C12—C13—C14 | 113.2 (4) | C13—C14—H14 | 107.0 |
C9—C14—C16 | 114.4 (4) | C11—C15—H15a | 109.5 |
C9—C14—C13 | 106.2 (4) | C11—C15—H15b | 109.5 |
C16—C14—C13 | 114.6 (4) | H15a—C15—H15b | 109.5 |
C18—C16—C17 | 110.3 (4) | C11—C15—H15c | 109.5 |
C18—C16—C14 | 115.2 (4) | H15a—C15—H15c | 109.5 |
C17—C16—C14 | 111.5 (4) | H15b—C15—H15c | 109.5 |
C3—C2—H2a | 109.0 | C18—C16—H16 | 106.4 |
N1—C2—H2a | 109.0 | C17—C16—H16 | 106.4 |
C3—C2—H2b | 109.0 | C14—C16—H16 | 106.4 |
N1—C2—H2b | 109.0 | C16—C17—H17a | 109.5 |
H2a—C2—H2b | 107.8 | C16—C17—H17b | 109.5 |
C2—C3—H3a | 109.5 | H17a—C17—H17b | 109.5 |
C2—C3—H3b | 109.5 | C16—C17—H17c | 109.5 |
H3a—C3—H3b | 109.5 | H17a—C17—H17c | 109.5 |
C2—C3—H3c | 109.5 | H17b—C17—H17c | 109.5 |
H3a—C3—H3c | 109.5 | C16—C18—H18a | 109.5 |
H3b—C3—H3c | 109.5 | C16—C18—H18b | 109.5 |
N1—C4—H4a | 109.2 | H18a—C18—H18b | 109.5 |
C5—C4—H4a | 109.2 | C16—C18—H18c | 109.5 |
N1—C4—H4b | 109.2 | H18a—C18—H18c | 109.5 |
C5—C4—H4b | 109.2 | H18b—C18—H18c | 109.5 |
C6—Sn1—S1—C1 | −49.1 (3) | S1—Sn1—C6—C7 | −18.4 (5) |
O1—Sn1—S1—C1 | −91.4 (1) | S2—Sn1—C6—C7 | −62.6 (3) |
Cl1—Sn1—S1—C1 | 90.4 (1) | Sn1—C6—C7—C8 | −32.0 (5) |
Cl2—Sn1—S1—C1 | −175.9 (1) | Sn1—O1—C8—O2 | −174.1 (3) |
S2—Sn1—S1—C1 | −1.0 (1) | Sn1—O1—C8—C7 | 5.2 (5) |
C6—Sn1—S2—C1 | 160.8 (2) | C9—O2—C8—O1 | −1.1 (6) |
O1—Sn1—S2—C1 | 85.3 (1) | C9—O2—C8—C7 | 179.5 (4) |
Cl1—Sn1—S2—C1 | −96.9 (1) | C6—C7—C8—O1 | 17.4 (6) |
Cl2—Sn1—S2—C1 | 15.7 (2) | C6—C7—C8—O2 | −163.3 (4) |
S1—Sn1—S2—C1 | 1.0 (1) | C8—O2—C9—C10 | −113.5 (4) |
C6—Sn1—O1—C8 | −17.9 (3) | C8—O2—C9—C14 | 124.7 (4) |
Cl2—Sn1—O1—C8 | −125.3 (3) | O2—C9—C10—C11 | 179.3 (4) |
S1—Sn1—O1—C8 | 143.3 (3) | C14—C9—C10—C11 | −61.5 (5) |
S2—Sn1—O1—C8 | 73.8 (3) | C9—C10—C11—C15 | 178.2 (4) |
C4—N1—C1—S2 | 0.3 (5) | C9—C10—C11—C12 | 55.3 (5) |
C2—N1—C1—S2 | 179.4 (3) | C15—C11—C12—C13 | −175.6 (5) |
C4—N1—C1—S1 | −179.5 (3) | C10—C11—C12—C13 | −53.1 (6) |
C2—N1—C1—S1 | −0.5 (5) | C11—C12—C13—C14 | 55.7 (6) |
Sn1—S2—C1—N1 | 178.6 (3) | O2—C9—C14—C16 | −54.8 (5) |
Sn1—S2—C1—S1 | −1.5 (2) | C10—C9—C14—C16 | −173.3 (3) |
Sn1—S1—C1—N1 | −178.5 (3) | O2—C9—C14—C13 | 177.7 (4) |
Sn1—S1—C1—S2 | 1.6 (2) | C10—C9—C14—C13 | 59.2 (5) |
C1—N1—C2—C3 | −98.2 (5) | C12—C13—C14—C9 | −56.4 (5) |
C4—N1—C2—C3 | 80.9 (5) | C12—C13—C14—C16 | 176.2 (4) |
C1—N1—C4—C5 | −92.0 (5) | C9—C14—C16—C18 | −64.3 (5) |
C2—N1—C4—C5 | 88.9 (4) | C13—C14—C16—C18 | 58.7 (5) |
O1—Sn1—C6—C7 | 25.3 (3) | C9—C14—C16—C17 | 169.0 (4) |
Cl1—Sn1—C6—C7 | −157.4 (3) | C13—C14—C16—C17 | −68.0 (5) |
Cl2—Sn1—C6—C7 | 105.5 (3) |