Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042675/sj2341sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042675/sj2341Isup2.hkl |
CCDC reference: 663558
To a solution of ZnCl2 (0.084 g, 0.61 mmol) in THF (10 ml) was added dropwise a solution of trans-(1R,2R)- N,N,N',N'-tetramethylcycloheane-1,2-diamine (0.93 g, 0.61 mmol) in THF (10 ml). The mixture was stirred for 2 days at room temperature. The solvent was removed and the residue was washed with ether to give a white solid. Colorless crystals was obtained from methanol solution. Yield; 1.40 g (75%). Anal. Calcd. for C10H22Cl2N2Zn: C, 39.18; H, 7.23; N, 9.14. Found: C, 39.15; H, 7.24; N, 9.10%. 1H NMR (CDCl3); δ 2.45(m, 4H, CHDA), 2.08(m, 2H, CHDA), 1.86(m, 2H, CHDA), 1.25(m, 1H, CHDA), 1.13(m, 1H, CHDA). 2.27(s, 12H, CH3).
The C3, C5, C6 and C8 carbon atoms of the cyclohexane ring are disordered over two positions. They were refined isotropically at half occupancies. All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.98 Å, Uiso = 1.2Ueq (C) for CH, 0.97 Å, Uiso = 1.2Ueq (C) for CH2 and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
Chiral N,N,N',N'-tetramethylcycloheane-1,2-diamine has been used as enantioselective additive for the asymmetric addition of aryl or alkyl lithium to pro-chiral imines (Cabello et al., 2005; Kizirian et al., 2005). Crystal structures of zinc complexes containing non-macrocyclic cyclohexane- 1,2-diamine as ligand are very rare (Roh et al., 2004). Herein, we report the crystal structure of the ZnII complex bearing N,N,N',N'-tetramethylcycloheane-1,2-diamine and two chloride anions. The geometry around ZnII is a near tetrahedron while the Cu(II) complex bearing the same ligand has a distorted square-planar geometry (Pavlova et al., 2003). The angles between N—Zn—N and Cl—Zn—Cl planes are 89.7 (2)°.
For the use of tetramethylcyclohexane-1,2-diamine in asymmetric addition, see: Cabello et al. (2005); Kizirian et al. (2005). For related structures, see: Roh et al. (2004); Pavlova et al. (2003).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD (McArdle, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEXIII (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[ZnCl2(C10H22N2)] | F(000) = 640 |
Mr = 306.59 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 8.2566 (6) Å | θ = 9.2–13.3° |
b = 14.1915 (13) Å | µ = 2.04 mm−1 |
c = 12.9584 (9) Å | T = 293 K |
β = 107.504 (6)° | Block, colorless |
V = 1448.1 (2) Å3 | 0.40 × 0.40 × 0.35 mm |
Z = 4 |
Enraf–Nonius CAD-4 four-circle diffractometer | 2388 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.011 |
Graphite monochromator | θmax = 25.5°, θmin = 2.2° |
scintillation counter scans | h = −9→9 |
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999) | k = −17→0 |
Tmin = 0.46, Tmax = 0.49 | l = 0→15 |
2918 measured reflections | 3 standard reflections every 60 min |
2687 independent reflections | intensity decay: 0.2% |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.28 | w = 1/[σ2(Fo2) + (0.0001P)2 + 8.9534P] where P = (Fo2 + 2Fc2)/3 |
2687 reflections | (Δ/σ)max < 0.001 |
132 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
[ZnCl2(C10H22N2)] | V = 1448.1 (2) Å3 |
Mr = 306.59 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.2566 (6) Å | µ = 2.04 mm−1 |
b = 14.1915 (13) Å | T = 293 K |
c = 12.9584 (9) Å | 0.40 × 0.40 × 0.35 mm |
β = 107.504 (6)° |
Enraf–Nonius CAD-4 four-circle diffractometer | 2388 reflections with I > 2σ(I) |
Absorption correction: ψ scan (ABSCALC; McArdle & Daly, 1999) | Rint = 0.011 |
Tmin = 0.46, Tmax = 0.49 | 3 standard reflections every 60 min |
2918 measured reflections | intensity decay: 0.2% |
2687 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.28 | Δρmax = 0.45 e Å−3 |
2687 reflections | Δρmin = −0.49 e Å−3 |
132 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn | 0.24797 (10) | 0.14548 (6) | 0.43395 (6) | 0.0467 (3) | |
Cl1 | 0.2396 (3) | 0.07751 (16) | 0.58652 (15) | 0.0690 (6) | |
Cl2 | 0.4590 (3) | 0.24418 (18) | 0.4487 (2) | 0.0833 (8) | |
N1 | 0.0079 (7) | 0.1968 (4) | 0.3495 (5) | 0.0476 (14) | |
N2 | 0.2142 (8) | 0.0459 (5) | 0.3122 (5) | 0.0562 (16) | |
C1 | −0.0956 (11) | 0.2038 (8) | 0.4228 (8) | 0.089 (3) | |
H1A | −0.0499 | 0.2517 | 0.4759 | 0.106* | |
H1B | −0.0949 | 0.1444 | 0.4585 | 0.106* | |
H1C | −0.2101 | 0.2198 | 0.3824 | 0.106* | |
C2 | 0.0250 (13) | 0.2904 (6) | 0.3069 (10) | 0.099 (4) | |
H2A | 0.1000 | 0.2872 | 0.2630 | 0.119* | |
H2B | 0.0708 | 0.3332 | 0.3659 | 0.119* | |
H2C | −0.0845 | 0.3124 | 0.2639 | 0.119* | |
C3 | −0.0397 (18) | 0.1419 (11) | 0.2458 (12) | 0.049 (3)* | 0.50 |
H3 | 0.0088 | 0.1744 | 0.1952 | 0.059* | 0.50 |
C3' | −0.0814 (17) | 0.1143 (10) | 0.2794 (11) | 0.040 (3)* | 0.50 |
H3' | −0.1085 | 0.0666 | 0.3263 | 0.048* | 0.50 |
C4 | −0.2412 (9) | 0.1412 (6) | 0.1940 (7) | 0.067 (2) | |
H4A | −0.2954 | 0.1121 | 0.2428 | 0.080* | |
H4B | −0.2846 | 0.2047 | 0.1779 | 0.080* | |
C5 | −0.273 (3) | 0.0825 (16) | 0.0888 (18) | 0.087 (6)* | 0.50 |
H5A | −0.3913 | 0.0641 | 0.0708 | 0.105* | 0.50 |
H5B | −0.2676 | 0.1282 | 0.0343 | 0.105* | 0.50 |
C5' | −0.330 (2) | 0.0612 (12) | 0.1266 (14) | 0.060 (4)* | 0.50 |
H5C | −0.3988 | 0.0852 | 0.0572 | 0.072* | 0.50 |
H5D | −0.4062 | 0.0322 | 0.1617 | 0.072* | 0.50 |
C6 | −0.211 (3) | 0.0220 (16) | 0.0704 (17) | 0.073 (5)* | 0.50 |
H6A | −0.1929 | 0.0326 | 0.0007 | 0.088* | 0.50 |
H6B | −0.2887 | −0.0307 | 0.0617 | 0.088* | 0.50 |
C6' | −0.204 (3) | −0.0172 (17) | 0.1069 (19) | 0.087 (6)* | 0.50 |
H6C | −0.2395 | −0.0770 | 0.1295 | 0.104* | 0.50 |
H6D | −0.2240 | −0.0213 | 0.0293 | 0.104* | 0.50 |
C7 | −0.0311 (12) | −0.0100 (7) | 0.1544 (7) | 0.075 (3) | |
H7A | −0.0397 | −0.0760 | 0.1715 | 0.090* | |
H7B | 0.0549 | −0.0052 | 0.1175 | 0.090* | |
C8 | 0.033 (2) | 0.0454 (12) | 0.2630 (14) | 0.053 (4)* | 0.50 |
H8 | −0.0157 | 0.0142 | 0.3142 | 0.064* | 0.50 |
C8' | 0.0396 (18) | 0.0717 (11) | 0.2248 (13) | 0.045 (3)* | 0.50 |
H8' | 0.0642 | 0.1207 | 0.1783 | 0.054* | 0.50 |
C9 | 0.3344 (12) | 0.0601 (9) | 0.2507 (8) | 0.099 (4) | |
H9A | 0.3239 | 0.0095 | 0.2000 | 0.118* | |
H9B | 0.4480 | 0.0613 | 0.2994 | 0.118* | |
H9C | 0.3104 | 0.1189 | 0.2124 | 0.118* | |
C10 | 0.2425 (18) | −0.0485 (7) | 0.3608 (10) | 0.117 (5) | |
H10A | 0.1814 | −0.0942 | 0.3089 | 0.140* | |
H10B | 0.2029 | −0.0502 | 0.4233 | 0.140* | |
H10C | 0.3616 | −0.0629 | 0.3819 | 0.140* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0422 (4) | 0.0500 (5) | 0.0456 (5) | −0.0030 (4) | 0.0101 (3) | 0.0028 (4) |
Cl1 | 0.0779 (14) | 0.0781 (14) | 0.0414 (10) | −0.0194 (11) | 0.0034 (9) | 0.0103 (9) |
Cl2 | 0.0577 (13) | 0.0751 (15) | 0.119 (2) | −0.0192 (11) | 0.0298 (13) | 0.0030 (14) |
N1 | 0.044 (3) | 0.046 (3) | 0.048 (3) | 0.006 (3) | 0.007 (3) | 0.002 (3) |
N2 | 0.053 (4) | 0.065 (4) | 0.057 (4) | 0.010 (3) | 0.026 (3) | 0.003 (3) |
C1 | 0.061 (6) | 0.135 (10) | 0.076 (6) | 0.025 (6) | 0.029 (5) | 0.009 (6) |
C2 | 0.090 (7) | 0.059 (6) | 0.138 (10) | 0.012 (5) | 0.016 (7) | 0.047 (6) |
C4 | 0.048 (4) | 0.069 (5) | 0.069 (5) | 0.006 (4) | −0.004 (4) | 0.010 (5) |
C7 | 0.087 (7) | 0.075 (6) | 0.059 (5) | −0.015 (5) | 0.018 (5) | −0.022 (5) |
C9 | 0.074 (6) | 0.153 (11) | 0.083 (7) | −0.005 (7) | 0.046 (6) | −0.028 (7) |
C10 | 0.205 (15) | 0.053 (6) | 0.103 (9) | 0.016 (8) | 0.062 (9) | −0.003 (6) |
Zn—N2 | 2.073 (7) | C4—H4A | 0.9700 |
Zn—N1 | 2.086 (6) | C4—H4B | 0.9700 |
Zn—Cl2 | 2.199 (2) | C5—C6 | 1.06 (2) |
Zn—Cl1 | 2.219 (2) | C5—H5A | 0.9700 |
N1—C1 | 1.461 (10) | C5—H5B | 0.9700 |
N1—C2 | 1.462 (10) | C5'—C6' | 1.59 (3) |
N1—C3 | 1.500 (15) | C5'—H5C | 0.9700 |
N1—C3' | 1.528 (14) | C5'—H5D | 0.9700 |
N2—C8 | 1.438 (16) | C6—C7 | 1.62 (2) |
N2—C9 | 1.462 (10) | C6—H6A | 0.9700 |
N2—C10 | 1.468 (11) | C6—H6B | 0.9700 |
N2—C8' | 1.585 (16) | C6'—C7 | 1.38 (2) |
C1—H1A | 0.9600 | C6'—H6C | 0.9700 |
C1—H1B | 0.9600 | C6'—H6D | 0.9700 |
C1—H1C | 0.9600 | C7—C8' | 1.482 (16) |
C2—H2A | 0.9600 | C7—C8 | 1.559 (17) |
C2—H2B | 0.9600 | C7—H7A | 0.9700 |
C2—H2C | 0.9600 | C7—H7B | 0.9700 |
C3—C8 | 1.49 (2) | C8—H8 | 0.9800 |
C3—C4 | 1.596 (16) | C8'—H8' | 0.9800 |
C3—H3 | 0.9800 | C9—H9A | 0.9600 |
C3'—C4 | 1.494 (14) | C9—H9B | 0.9600 |
C3'—C8' | 1.513 (19) | C9—H9C | 0.9600 |
C3'—H3' | 0.9800 | C10—H10A | 0.9600 |
C4—C5' | 1.485 (18) | C10—H10B | 0.9600 |
C4—C5 | 1.55 (2) | C10—H10C | 0.9600 |
N2—Zn—N1 | 87.1 (2) | H4A—C4—H4B | 108.9 |
N2—Zn—Cl2 | 114.97 (19) | C6—C5—C4 | 132 (2) |
N1—Zn—Cl2 | 115.24 (18) | C6—C5—H5A | 104.3 |
N2—Zn—Cl1 | 110.38 (19) | C4—C5—H5A | 104.3 |
N1—Zn—Cl1 | 109.88 (18) | C6—C5—H5B | 104.3 |
Cl2—Zn—Cl1 | 115.83 (10) | C4—C5—H5B | 104.3 |
C1—N1—C2 | 109.0 (8) | H5A—C5—H5B | 105.6 |
C1—N1—C3 | 124.9 (9) | C4—C5'—C6' | 113.4 (14) |
C2—N1—C3 | 99.4 (9) | C4—C5'—H5C | 108.9 |
C1—N1—C3' | 99.6 (8) | C6'—C5'—H5C | 108.9 |
C2—N1—C3' | 123.8 (8) | C4—C5'—H5D | 108.9 |
C3—N1—C3' | 28.4 (6) | C6'—C5'—H5D | 108.9 |
C1—N1—Zn | 109.4 (5) | H5C—C5'—H5D | 107.7 |
C2—N1—Zn | 109.3 (5) | C5—C6—C7 | 119 (2) |
C3—N1—Zn | 103.9 (6) | C5—C6—H6A | 107.6 |
C3'—N1—Zn | 104.9 (6) | C7—C6—H6A | 107.6 |
C8—N2—C9 | 123.0 (10) | C5—C6—H6B | 107.6 |
C8—N2—C10 | 101.3 (10) | C7—C6—H6B | 107.6 |
C9—N2—C10 | 108.2 (8) | H6A—C6—H6B | 107.0 |
C8—N2—C8' | 23.6 (7) | C7—C6'—C5' | 120.9 (17) |
C9—N2—C8' | 101.5 (8) | C7—C6'—H6C | 107.1 |
C10—N2—C8' | 120.7 (9) | C5'—C6'—H6C | 107.1 |
C8—N2—Zn | 103.0 (7) | C7—C6'—H6D | 107.1 |
C9—N2—Zn | 111.2 (6) | C5'—C6'—H6D | 107.1 |
C10—N2—Zn | 109.2 (6) | H6C—C6'—H6D | 106.8 |
C8'—N2—Zn | 105.7 (6) | C6'—C7—C8' | 119.7 (13) |
N1—C1—H1A | 109.5 | C6'—C7—C8 | 117.7 (13) |
N1—C1—H1B | 109.5 | C8'—C7—C8 | 23.9 (7) |
H1A—C1—H1B | 109.5 | C6'—C7—C6 | 26.3 (11) |
N1—C1—H1C | 109.5 | C8'—C7—C6 | 107.8 (11) |
H1A—C1—H1C | 109.5 | C8—C7—C6 | 117.4 (11) |
H1B—C1—H1C | 109.5 | C6'—C7—H7A | 83.8 |
N1—C2—H2A | 109.5 | C8'—C7—H7A | 131.0 |
N1—C2—H2B | 109.5 | C8—C7—H7A | 108.0 |
H2A—C2—H2B | 109.5 | C6—C7—H7A | 108.0 |
N1—C2—H2C | 109.5 | C6'—C7—H7B | 126.8 |
H2A—C2—H2C | 109.5 | C8'—C7—H7B | 92.1 |
H2B—C2—H2C | 109.5 | C8—C7—H7B | 108.0 |
C8—C3—N1 | 111.0 (12) | C6—C7—H7B | 108.0 |
C8—C3—C4 | 112.4 (12) | H7A—C7—H7B | 107.2 |
N1—C3—C4 | 109.8 (10) | N2—C8—C3 | 112.5 (13) |
C8—C3—H3 | 107.8 | N2—C8—C7 | 115.4 (11) |
N1—C3—H3 | 107.8 | C3—C8—C7 | 108.5 (13) |
C4—C3—H3 | 107.8 | N2—C8—H8 | 106.7 |
C4—C3'—C8' | 108.4 (11) | C3—C8—H8 | 106.7 |
C4—C3'—N1 | 113.9 (10) | C7—C8—H8 | 106.7 |
C8'—C3'—N1 | 108.4 (10) | C7—C8'—C3' | 114.1 (12) |
C4—C3'—H3' | 108.7 | C7—C8'—N2 | 111.3 (11) |
C8'—C3'—H3' | 108.7 | C3'—C8'—N2 | 110.2 (11) |
N1—C3'—H3' | 108.7 | C7—C8'—H8' | 107.0 |
C5'—C4—C3' | 114.3 (10) | C3'—C8'—H8' | 107.0 |
C5'—C4—C5 | 31.8 (9) | N2—C8'—H8' | 107.0 |
C3'—C4—C5 | 113.1 (11) | N2—C9—H9A | 109.5 |
C5'—C4—C3 | 121.4 (10) | N2—C9—H9B | 109.5 |
C3'—C4—C3 | 27.6 (6) | H9A—C9—H9B | 109.5 |
C5—C4—C3 | 104.6 (11) | N2—C9—H9C | 109.5 |
C5'—C4—H4A | 79.3 | H9A—C9—H9C | 109.5 |
C3'—C4—H4A | 83.5 | H9B—C9—H9C | 109.5 |
C5—C4—H4A | 110.8 | N2—C10—H10A | 109.5 |
C3—C4—H4A | 110.8 | N2—C10—H10B | 109.5 |
C5'—C4—H4B | 119.9 | H10A—C10—H10B | 109.5 |
C3'—C4—H4B | 125.7 | N2—C10—H10C | 109.5 |
C5—C4—H4B | 110.8 | H10A—C10—H10C | 109.5 |
C3—C4—H4B | 110.8 | H10B—C10—H10C | 109.5 |
N2—Zn—N1—C1 | 128.6 (6) | N1—C3—C4—C5 | −179.8 (12) |
Cl2—Zn—N1—C1 | −115.1 (6) | C5'—C4—C5—C6 | −90 (4) |
Cl1—Zn—N1—C1 | 17.9 (6) | C3'—C4—C5—C6 | 9 (4) |
N2—Zn—N1—C2 | −112.2 (6) | C3—C4—C5—C6 | 37 (3) |
Cl2—Zn—N1—C2 | 4.1 (7) | C3'—C4—C5'—C6' | −33.8 (19) |
Cl1—Zn—N1—C2 | 137.2 (6) | C5—C4—C5'—C6' | 61 (2) |
N2—Zn—N1—C3 | −6.8 (8) | C3—C4—C5'—C6' | −4 (2) |
Cl2—Zn—N1—C3 | 109.5 (7) | C4—C5—C6—C7 | −12 (4) |
Cl1—Zn—N1—C3 | −117.4 (7) | C4—C5'—C6'—C7 | 3 (3) |
N2—Zn—N1—C3' | 22.5 (7) | C5'—C6'—C7—C8' | 0 (3) |
Cl2—Zn—N1—C3' | 138.8 (6) | C5'—C6'—C7—C8 | 27 (3) |
Cl1—Zn—N1—C3' | −88.2 (7) | C5'—C6'—C7—C6 | −69 (3) |
N1—Zn—N2—C8 | −19.6 (9) | C5—C6—C7—C6' | 103 (4) |
Cl2—Zn—N2—C8 | −136.2 (8) | C5—C6—C7—C8' | −19 (3) |
Cl1—Zn—N2—C8 | 90.5 (8) | C5—C6—C7—C8 | 5 (3) |
N1—Zn—N2—C9 | 113.9 (6) | C9—N2—C8—C3 | −82.1 (16) |
Cl2—Zn—N2—C9 | −2.6 (7) | C10—N2—C8—C3 | 157.2 (13) |
Cl1—Zn—N2—C9 | −135.9 (6) | C8'—N2—C8—C3 | −55 (2) |
N1—Zn—N2—C10 | −126.7 (7) | Zn—N2—C8—C3 | 44.3 (15) |
Cl2—Zn—N2—C10 | 116.8 (7) | C9—N2—C8—C7 | 43.1 (18) |
Cl1—Zn—N2—C10 | −16.5 (7) | C10—N2—C8—C7 | −77.6 (14) |
N1—Zn—N2—C8' | 4.6 (7) | C8'—N2—C8—C7 | 70 (2) |
Cl2—Zn—N2—C8' | −112.0 (7) | Zn—N2—C8—C7 | 169.4 (10) |
Cl1—Zn—N2—C8' | 114.7 (7) | N1—C3—C8—N2 | −55.0 (18) |
C1—N1—C3—C8 | −93.7 (14) | C4—C3—C8—N2 | −178.4 (10) |
C2—N1—C3—C8 | 145.1 (12) | N1—C3—C8—C7 | 176.1 (10) |
C3'—N1—C3—C8 | −63.3 (17) | C4—C3—C8—C7 | 52.7 (17) |
Zn—N1—C3—C8 | 32.4 (14) | C6'—C7—C8—N2 | 176.4 (15) |
C1—N1—C3—C4 | 31.2 (15) | C8'—C7—C8—N2 | −82 (2) |
C2—N1—C3—C4 | −89.9 (11) | C6—C7—C8—N2 | −153.9 (13) |
C3'—N1—C3—C4 | 61.7 (16) | C6'—C7—C8—C3 | −56 (2) |
Zn—N1—C3—C4 | 157.3 (8) | C8'—C7—C8—C3 | 45 (2) |
C1—N1—C3'—C4 | 79.6 (11) | C6—C7—C8—C3 | −26.7 (19) |
C2—N1—C3'—C4 | −41.1 (14) | C6'—C7—C8'—C3' | 27 (2) |
C3—N1—C3'—C4 | −75.5 (18) | C8—C7—C8'—C3' | −65 (2) |
Zn—N1—C3'—C4 | −167.2 (8) | C6—C7—C8'—C3' | 53.0 (17) |
C1—N1—C3'—C8' | −159.6 (11) | C6'—C7—C8'—N2 | 152.6 (15) |
C2—N1—C3'—C8' | 79.7 (13) | C8—C7—C8'—N2 | 61 (2) |
C3—N1—C3'—C8' | 45.4 (16) | C6—C7—C8'—N2 | 178.4 (11) |
Zn—N1—C3'—C8' | −46.4 (12) | C4—C3'—C8'—C7 | −56.2 (16) |
C8'—C3'—C4—C5' | 60.1 (15) | N1—C3'—C8'—C7 | 179.6 (10) |
N1—C3'—C4—C5' | −179.1 (11) | C4—C3'—C8'—N2 | 177.7 (10) |
C8'—C3'—C4—C5 | 25.3 (17) | N1—C3'—C8'—N2 | 53.6 (14) |
N1—C3'—C4—C5 | 146.2 (12) | C8—N2—C8'—C7 | −73 (2) |
C8'—C3'—C4—C3 | −51.7 (16) | C9—N2—C8'—C7 | 84.1 (12) |
N1—C3'—C4—C3 | 69.2 (17) | C10—N2—C8'—C7 | −35.4 (15) |
C8—C3—C4—C5' | −26.1 (19) | Zn—N2—C8'—C7 | −159.7 (9) |
N1—C3—C4—C5' | −150.3 (12) | C8—N2—C8'—C3' | 54 (2) |
C8—C3—C4—C3' | 56.5 (17) | C9—N2—C8'—C3' | −148.3 (12) |
N1—C3—C4—C3' | −67.6 (16) | C10—N2—C8'—C3' | 92.2 (13) |
C8—C3—C4—C5 | −55.6 (17) | Zn—N2—C8'—C3' | −32.2 (13) |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C10H22N2)] |
Mr | 306.59 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.2566 (6), 14.1915 (13), 12.9584 (9) |
β (°) | 107.504 (6) |
V (Å3) | 1448.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.04 |
Crystal size (mm) | 0.40 × 0.40 × 0.35 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 four-circle |
Absorption correction | ψ scan (ABSCALC; McArdle & Daly, 1999) |
Tmin, Tmax | 0.46, 0.49 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2918, 2687, 2388 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.605 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.159, 1.28 |
No. of reflections | 2687 |
No. of parameters | 132 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.49 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD (McArdle, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEXIII (McArdle, 1995).
Zn—N2 | 2.073 (7) | Zn—Cl2 | 2.199 (2) |
Zn—N1 | 2.086 (6) | Zn—Cl1 | 2.219 (2) |
N2—Zn—N1 | 87.1 (2) | N2—Zn—Cl1 | 110.38 (19) |
N2—Zn—Cl2 | 114.97 (19) | N1—Zn—Cl1 | 109.88 (18) |
N1—Zn—Cl2 | 115.24 (18) | Cl2—Zn—Cl1 | 115.83 (10) |
Chiral N,N,N',N'-tetramethylcycloheane-1,2-diamine has been used as enantioselective additive for the asymmetric addition of aryl or alkyl lithium to pro-chiral imines (Cabello et al., 2005; Kizirian et al., 2005). Crystal structures of zinc complexes containing non-macrocyclic cyclohexane- 1,2-diamine as ligand are very rare (Roh et al., 2004). Herein, we report the crystal structure of the ZnII complex bearing N,N,N',N'-tetramethylcycloheane-1,2-diamine and two chloride anions. The geometry around ZnII is a near tetrahedron while the Cu(II) complex bearing the same ligand has a distorted square-planar geometry (Pavlova et al., 2003). The angles between N—Zn—N and Cl—Zn—Cl planes are 89.7 (2)°.