Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039474/ci6699sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039474/ci6699Isup2.hkl |
CCDC reference: 296530
N-Cyclohexyl-1,3-diaminopropane (0.1 mmol, 15.6 mg) and 3-methylsalicylaldehyde (0.1 mmol, 13.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. To this solution was added a MeOH solution (5 ml) of ZnCl2 (0.1 mmol, 13.6 mg), with stirring. The resulting mixture was stirred for another 10 min at room temperature. After keeping the filtrate in air for 16 d, colourless block-shaped crystals were formed at the bottom of the vessel.
The cyclohexyl group is disordered over two distinct sites, with occupancy factors of 0.761 (6) and 0.239 (6). The C—C and N—C distances involving the disordered atoms were restrained to 1.53 (1) and 1.46 (1) Å, respectively. The Uij components of the disordered atoms were approximated to isotropic behaviour. H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, N—H distances of 0.90 Å, and with Uiso(H) = 1.2–1.5Ueq(C/N).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
[ZnCl2(C17H26N2O)] | F(000) = 1712 |
Mr = 410.67 | Dx = 1.449 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5157 reflections |
a = 35.492 (3) Å | θ = 2.7–25.0° |
b = 7.482 (1) Å | µ = 1.59 mm−1 |
c = 15.011 (1) Å | T = 298 K |
β = 109.132 (1)° | Block, colourless |
V = 3766.0 (6) Å3 | 0.25 × 0.24 × 0.13 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 4483 independent reflections |
Radiation source: fine-focus sealed tube | 3472 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 28.4°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −46→45 |
Tmin = 0.692, Tmax = 0.820 | k = −9→9 |
15865 measured reflections | l = −19→19 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.065P)2 + 2.2034P] where P = (Fo2 + 2Fc2)/3 |
4483 reflections | (Δ/σ)max = 0.001 |
264 parameters | Δρmax = 0.57 e Å−3 |
86 restraints | Δρmin = −0.29 e Å−3 |
[ZnCl2(C17H26N2O)] | V = 3766.0 (6) Å3 |
Mr = 410.67 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 35.492 (3) Å | µ = 1.59 mm−1 |
b = 7.482 (1) Å | T = 298 K |
c = 15.011 (1) Å | 0.25 × 0.24 × 0.13 mm |
β = 109.132 (1)° |
Bruker SMART CCD area-detector diffractometer | 4483 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3472 reflections with I > 2σ(I) |
Tmin = 0.692, Tmax = 0.820 | Rint = 0.026 |
15865 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 86 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.57 e Å−3 |
4483 reflections | Δρmin = −0.29 e Å−3 |
264 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.823600 (9) | 1.20860 (4) | 0.98841 (2) | 0.04329 (12) | |
Cl1 | 0.80610 (2) | 1.48343 (10) | 0.93101 (5) | 0.05590 (19) | |
Cl2 | 0.80364 (2) | 1.13639 (10) | 1.11222 (5) | 0.0581 (2) | |
N1 | 0.80821 (6) | 1.0137 (3) | 0.89124 (15) | 0.0421 (5) | |
N2 | 0.67447 (7) | 0.7970 (3) | 0.87195 (17) | 0.0500 (6) | |
H2A | 0.6802 | 0.8537 | 0.9277 | 0.060* | 0.761 (6) |
H2B | 0.6836 | 0.6844 | 0.8849 | 0.060* | 0.761 (6) |
H2C | 0.6760 | 0.8576 | 0.9248 | 0.060* | 0.239 (6) |
H2D | 0.6818 | 0.6827 | 0.8868 | 0.060* | 0.239 (6) |
O1 | 0.88009 (6) | 1.1832 (3) | 1.01811 (18) | 0.0662 (6) | |
C1 | 0.89736 (9) | 1.0436 (4) | 0.9987 (2) | 0.0575 (7) | |
C2 | 0.93958 (10) | 1.0310 (5) | 1.0408 (3) | 0.0755 (10) | |
C3 | 0.95894 (12) | 0.8821 (7) | 1.0247 (4) | 0.1044 (16) | |
H3 | 0.9864 | 0.8741 | 1.0532 | 0.125* | |
C4 | 0.93929 (14) | 0.7451 (7) | 0.9684 (4) | 0.118 (2) | |
H4 | 0.9533 | 0.6452 | 0.9599 | 0.142* | |
C5 | 0.89894 (13) | 0.7550 (6) | 0.9245 (3) | 0.0893 (13) | |
H5 | 0.8858 | 0.6617 | 0.8858 | 0.107* | |
C6 | 0.87713 (9) | 0.9045 (4) | 0.9370 (2) | 0.0577 (7) | |
C7 | 0.96131 (11) | 1.1805 (7) | 1.1028 (3) | 0.0979 (15) | |
H7A | 0.9894 | 1.1550 | 1.1251 | 0.147* | |
H7B | 0.9518 | 1.1924 | 1.1555 | 0.147* | |
H7C | 0.9567 | 1.2898 | 1.0674 | 0.147* | |
C8 | 0.83514 (8) | 0.9045 (4) | 0.8839 (2) | 0.0484 (6) | |
H8 | 0.8264 | 0.8149 | 0.8389 | 0.058* | |
C9 | 0.76716 (8) | 0.9864 (4) | 0.82934 (18) | 0.0465 (6) | |
H9A | 0.7672 | 0.9135 | 0.7759 | 0.056* | |
H9B | 0.7553 | 1.1010 | 0.8054 | 0.056* | |
C10 | 0.74222 (7) | 0.8952 (4) | 0.88143 (19) | 0.0434 (6) | |
H10A | 0.7525 | 0.7760 | 0.9001 | 0.052* | |
H10B | 0.7442 | 0.9621 | 0.9381 | 0.052* | |
C11 | 0.69914 (7) | 0.8831 (4) | 0.82036 (18) | 0.0465 (6) | |
H11A | 0.6890 | 1.0022 | 0.8007 | 0.056* | |
H11B | 0.6971 | 0.8143 | 0.7642 | 0.056* | |
C12 | 0.62993 (12) | 0.7846 (7) | 0.8325 (4) | 0.0539 (12) | 0.761 (6) |
H12A | 0.6204 | 0.7257 | 0.8794 | 0.065* | 0.761 (6) |
C13 | 0.61831 (11) | 0.6698 (6) | 0.7446 (3) | 0.0620 (13) | 0.761 (6) |
H13A | 0.6308 | 0.5533 | 0.7592 | 0.074* | 0.761 (6) |
H13B | 0.6274 | 0.7253 | 0.6969 | 0.074* | 0.761 (6) |
C14 | 0.57293 (14) | 0.6486 (8) | 0.7072 (4) | 0.0819 (16) | 0.761 (6) |
H14A | 0.5652 | 0.5769 | 0.6502 | 0.098* | 0.761 (6) |
H14B | 0.5639 | 0.5885 | 0.7538 | 0.098* | 0.761 (6) |
C15 | 0.55447 (17) | 0.8285 (8) | 0.6868 (4) | 0.100 (2) | 0.761 (6) |
H15A | 0.5257 | 0.8165 | 0.6611 | 0.120* | 0.761 (6) |
H15B | 0.5636 | 0.8877 | 0.6401 | 0.120* | 0.761 (6) |
C16 | 0.5656 (2) | 0.9420 (13) | 0.7772 (6) | 0.121 (3) | 0.761 (6) |
H16A | 0.5570 | 0.8829 | 0.8246 | 0.145* | 0.761 (6) |
H16B | 0.5527 | 1.0577 | 0.7639 | 0.145* | 0.761 (6) |
C17 | 0.6115 (2) | 0.9656 (11) | 0.8137 (8) | 0.094 (4) | 0.761 (6) |
H17A | 0.6202 | 1.0269 | 0.7668 | 0.113* | 0.761 (6) |
H17B | 0.6195 | 1.0362 | 0.8710 | 0.113* | 0.761 (6) |
C12' | 0.6335 (3) | 0.807 (3) | 0.7996 (10) | 0.069 (6) | 0.239 (6) |
H12B | 0.6360 | 0.7795 | 0.7379 | 0.082* | 0.239 (6) |
C13' | 0.6041 (4) | 0.671 (3) | 0.8175 (14) | 0.094 (6) | 0.239 (6) |
H13C | 0.6046 | 0.6862 | 0.8820 | 0.113* | 0.239 (6) |
H13D | 0.6142 | 0.5520 | 0.8128 | 0.113* | 0.239 (6) |
C14' | 0.5599 (4) | 0.677 (2) | 0.7529 (14) | 0.085 (5) | 0.239 (6) |
H14C | 0.5584 | 0.6520 | 0.6884 | 0.102* | 0.239 (6) |
H14D | 0.5448 | 0.5865 | 0.7726 | 0.102* | 0.239 (6) |
C15' | 0.5422 (6) | 0.857 (2) | 0.7574 (18) | 0.113 (7) | 0.239 (6) |
H15C | 0.5417 | 0.8814 | 0.8205 | 0.136* | 0.239 (6) |
H15D | 0.5152 | 0.8643 | 0.7136 | 0.136* | 0.239 (6) |
C16' | 0.5692 (5) | 0.989 (3) | 0.7306 (15) | 0.073 (5) | 0.239 (6) |
H16C | 0.5588 | 1.1086 | 0.7323 | 0.088* | 0.239 (6) |
H16D | 0.5677 | 0.9653 | 0.6660 | 0.088* | 0.239 (6) |
C17' | 0.6132 (6) | 0.987 (3) | 0.792 (2) | 0.065 (7) | 0.239 (6) |
H17C | 0.6276 | 1.0728 | 0.7673 | 0.078* | 0.239 (6) |
H17D | 0.6151 | 1.0260 | 0.8554 | 0.078* | 0.239 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.04106 (19) | 0.03869 (19) | 0.0495 (2) | −0.00158 (12) | 0.01401 (14) | −0.00496 (12) |
Cl1 | 0.0666 (4) | 0.0439 (4) | 0.0557 (4) | 0.0047 (3) | 0.0181 (3) | 0.0052 (3) |
Cl2 | 0.0746 (5) | 0.0519 (4) | 0.0519 (4) | −0.0020 (3) | 0.0264 (4) | 0.0000 (3) |
N1 | 0.0404 (11) | 0.0426 (11) | 0.0439 (11) | −0.0049 (9) | 0.0147 (9) | −0.0043 (9) |
N2 | 0.0411 (12) | 0.0486 (13) | 0.0589 (14) | −0.0035 (10) | 0.0146 (10) | −0.0061 (11) |
O1 | 0.0399 (10) | 0.0624 (13) | 0.0904 (16) | −0.0021 (9) | 0.0135 (11) | −0.0266 (12) |
C1 | 0.0436 (15) | 0.0557 (17) | 0.0697 (19) | 0.0029 (13) | 0.0140 (14) | −0.0060 (15) |
C2 | 0.0460 (17) | 0.081 (2) | 0.088 (2) | 0.0105 (16) | 0.0068 (17) | −0.012 (2) |
C3 | 0.056 (2) | 0.100 (3) | 0.134 (4) | 0.026 (2) | 0.000 (2) | −0.021 (3) |
C4 | 0.071 (3) | 0.093 (3) | 0.169 (5) | 0.041 (2) | 0.011 (3) | −0.036 (3) |
C5 | 0.070 (2) | 0.070 (2) | 0.117 (3) | 0.0170 (19) | 0.017 (2) | −0.027 (2) |
C6 | 0.0476 (15) | 0.0536 (17) | 0.0702 (19) | 0.0064 (13) | 0.0170 (14) | −0.0076 (14) |
C7 | 0.049 (2) | 0.110 (4) | 0.114 (4) | −0.003 (2) | −0.001 (2) | −0.028 (3) |
C8 | 0.0532 (15) | 0.0424 (14) | 0.0502 (15) | −0.0041 (12) | 0.0179 (12) | −0.0079 (11) |
C9 | 0.0447 (14) | 0.0494 (15) | 0.0440 (14) | −0.0045 (12) | 0.0126 (11) | 0.0008 (12) |
C10 | 0.0397 (13) | 0.0422 (14) | 0.0464 (13) | 0.0012 (11) | 0.0117 (11) | 0.0023 (11) |
C11 | 0.0438 (14) | 0.0469 (15) | 0.0445 (14) | −0.0041 (11) | 0.0087 (11) | 0.0002 (12) |
C12 | 0.038 (2) | 0.070 (3) | 0.057 (3) | −0.0134 (19) | 0.0201 (19) | −0.011 (2) |
C13 | 0.050 (2) | 0.065 (3) | 0.062 (2) | −0.0047 (19) | 0.0055 (18) | −0.024 (2) |
C14 | 0.060 (3) | 0.097 (4) | 0.079 (3) | −0.021 (3) | 0.008 (2) | −0.026 (3) |
C15 | 0.062 (3) | 0.103 (4) | 0.101 (4) | 0.006 (3) | −0.020 (3) | −0.027 (3) |
C16 | 0.066 (4) | 0.120 (6) | 0.154 (7) | 0.020 (4) | 0.005 (4) | −0.048 (5) |
C17 | 0.060 (4) | 0.082 (5) | 0.115 (7) | 0.013 (3) | −0.006 (4) | −0.039 (4) |
C12' | 0.055 (7) | 0.088 (9) | 0.083 (10) | −0.013 (6) | 0.049 (7) | 0.010 (7) |
C13' | 0.078 (9) | 0.088 (9) | 0.106 (10) | −0.014 (7) | 0.016 (7) | 0.008 (7) |
C14' | 0.077 (8) | 0.086 (9) | 0.084 (9) | −0.041 (7) | 0.015 (7) | −0.013 (7) |
C15' | 0.093 (10) | 0.130 (11) | 0.110 (11) | −0.015 (9) | 0.023 (8) | 0.015 (9) |
C16' | 0.047 (7) | 0.073 (8) | 0.091 (9) | 0.007 (6) | 0.012 (7) | 0.000 (7) |
C17' | 0.059 (10) | 0.059 (9) | 0.074 (10) | −0.011 (7) | 0.017 (7) | 0.005 (7) |
Zn1—O1 | 1.915 (2) | C11—H11B | 0.97 |
Zn1—N1 | 2.007 (2) | C12—C17 | 1.490 (7) |
Zn1—Cl1 | 2.2373 (8) | C12—C13 | 1.514 (5) |
Zn1—Cl2 | 2.2606 (8) | C12—H12A | 0.98 |
N1—C8 | 1.289 (3) | C13—C14 | 1.530 (5) |
N1—C9 | 1.463 (3) | C13—H13A | 0.97 |
N2—C11 | 1.492 (3) | C13—H13B | 0.97 |
N2—C12 | 1.498 (4) | C14—C15 | 1.484 (6) |
N2—C12' | 1.506 (10) | C14—H14A | 0.97 |
N2—H2A | 0.90 | C14—H14B | 0.97 |
N2—H2B | 0.90 | C15—C16 | 1.538 (7) |
N2—H2C | 0.90 | C15—H15A | 0.97 |
N2—H2D | 0.90 | C15—H15B | 0.97 |
O1—C1 | 1.292 (4) | C16—C17 | 1.549 (7) |
C1—C6 | 1.421 (4) | C16—H16A | 0.97 |
C1—C2 | 1.426 (4) | C16—H16B | 0.97 |
C2—C3 | 1.371 (5) | C17—H17A | 0.97 |
C2—C7 | 1.497 (5) | C17—H17B | 0.97 |
C3—C4 | 1.366 (7) | C12'—C17' | 1.517 (10) |
C3—H3 | 0.93 | C12'—C13' | 1.540 (10) |
C4—C5 | 1.368 (6) | C12'—H12B | 0.98 |
C4—H4 | 0.93 | C13'—C14' | 1.550 (10) |
C5—C6 | 1.407 (5) | C13'—H13C | 0.97 |
C5—H5 | 0.93 | C13'—H13D | 0.97 |
C6—C8 | 1.442 (4) | C14'—C15' | 1.498 (10) |
C7—H7A | 0.96 | C14'—H14C | 0.97 |
C7—H7B | 0.96 | C14'—H14D | 0.97 |
C7—H7C | 0.96 | C15'—C16' | 1.518 (10) |
C8—H8 | 0.93 | C15'—H15C | 0.97 |
C9—C10 | 1.521 (4) | C15'—H15D | 0.97 |
C9—H9A | 0.97 | C16'—C17' | 1.532 (10) |
C9—H9B | 0.97 | C16'—H16C | 0.97 |
C10—C11 | 1.506 (3) | C16'—H16D | 0.97 |
C10—H10A | 0.97 | C17'—H17C | 0.97 |
C10—H10B | 0.97 | C17'—H17D | 0.97 |
C11—H11A | 0.97 | ||
O1—Zn1—N1 | 96.43 (9) | C17—C12—N2 | 111.0 (4) |
O1—Zn1—Cl1 | 108.55 (8) | C17—C12—C13 | 111.9 (6) |
N1—Zn1—Cl1 | 114.37 (7) | N2—C12—C13 | 109.3 (3) |
O1—Zn1—Cl2 | 111.78 (8) | C17—C12—H12A | 108.2 |
N1—Zn1—Cl2 | 109.86 (6) | N2—C12—H12A | 108.2 |
Cl1—Zn1—Cl2 | 114.46 (3) | C13—C12—H12A | 108.2 |
C8—N1—C9 | 118.0 (2) | C12—C13—C14 | 109.4 (4) |
C8—N1—Zn1 | 119.30 (18) | C12—C13—H13A | 109.8 |
C9—N1—Zn1 | 122.70 (17) | C14—C13—H13A | 109.8 |
C11—N2—C12 | 122.9 (3) | C12—C13—H13B | 109.8 |
C11—N2—C12' | 101.4 (6) | C14—C13—H13B | 109.8 |
C11—N2—H2A | 106.6 | H13A—C13—H13B | 108.3 |
C12—N2—H2A | 106.6 | C15—C14—C13 | 108.8 (4) |
C12'—N2—H2A | 121.3 | C15—C14—H14A | 109.9 |
C11—N2—H2B | 106.6 | C13—C14—H14A | 109.9 |
C12—N2—H2B | 106.6 | C15—C14—H14B | 109.9 |
C12'—N2—H2B | 113.2 | C13—C14—H14B | 109.9 |
H2A—N2—H2B | 106.6 | H14A—C14—H14B | 108.3 |
C11—N2—H2C | 111.4 | C14—C15—C16 | 110.5 (6) |
C12'—N2—H2C | 112.0 | C14—C15—H15A | 109.6 |
H2B—N2—H2C | 111.7 | C16—C15—H15A | 109.6 |
C11—N2—H2D | 111.5 | C14—C15—H15B | 109.6 |
C12—N2—H2D | 102.8 | C16—C15—H15B | 109.6 |
C12'—N2—H2D | 110.9 | H15A—C15—H15B | 108.1 |
H2A—N2—H2D | 105.0 | C15—C16—C17 | 108.2 (6) |
H2C—N2—H2D | 109.4 | C15—C16—H16A | 110.1 |
C1—O1—Zn1 | 124.43 (19) | C17—C16—H16A | 110.1 |
O1—C1—C6 | 124.3 (3) | C15—C16—H16B | 110.1 |
O1—C1—C2 | 117.4 (3) | C17—C16—H16B | 110.1 |
C6—C1—C2 | 118.3 (3) | H16A—C16—H16B | 108.4 |
C3—C2—C1 | 119.3 (4) | C12—C17—C16 | 107.9 (6) |
C3—C2—C7 | 122.0 (3) | C12—C17—H17A | 110.1 |
C1—C2—C7 | 118.6 (3) | C16—C17—H17A | 110.1 |
C4—C3—C2 | 122.3 (4) | C12—C17—H17B | 110.1 |
C4—C3—H3 | 118.8 | C16—C17—H17B | 110.1 |
C2—C3—H3 | 118.8 | H17A—C17—H17B | 108.4 |
C3—C4—C5 | 119.9 (4) | N2—C12'—C17' | 114.7 (13) |
C3—C4—H4 | 120.0 | N2—C12'—C13' | 113.0 (10) |
C5—C4—H4 | 120.0 | C17'—C12'—C13' | 105.4 (15) |
C4—C5—C6 | 120.9 (4) | N2—C12'—H12B | 107.8 |
C4—C5—H5 | 119.6 | C17'—C12'—H12B | 107.8 |
C6—C5—H5 | 119.6 | C13'—C12'—H12B | 107.8 |
C5—C6—C1 | 119.1 (3) | C12'—C13'—C14' | 118.2 (12) |
C5—C6—C8 | 116.2 (3) | C12'—C13'—H13C | 107.7 |
C1—C6—C8 | 124.7 (3) | C14'—C13'—H13C | 107.7 |
C2—C7—H7A | 109.5 | C12'—C13'—H13D | 107.7 |
C2—C7—H7B | 109.5 | C14'—C13'—H13D | 107.7 |
H7A—C7—H7B | 109.5 | H13C—C13'—H13D | 107.1 |
C2—C7—H7C | 109.5 | C15'—C14'—C13' | 110.7 (16) |
H7A—C7—H7C | 109.5 | C15'—C14'—H14C | 109.5 |
H7B—C7—H7C | 109.5 | C13'—C14'—H14C | 109.5 |
N1—C8—C6 | 127.9 (3) | C15'—C14'—H14D | 109.5 |
N1—C8—H8 | 116.1 | C13'—C14'—H14D | 109.5 |
C6—C8—H8 | 116.1 | H14C—C14'—H14D | 108.1 |
N1—C9—C10 | 111.2 (2) | C14'—C15'—C16' | 105.1 (16) |
N1—C9—H9A | 109.4 | C14'—C15'—H15C | 110.7 |
C10—C9—H9A | 109.4 | C16'—C15'—H15C | 110.7 |
N1—C9—H9B | 109.4 | C14'—C15'—H15D | 110.7 |
C10—C9—H9B | 109.4 | C16'—C15'—H15D | 110.7 |
H9A—C9—H9B | 108.0 | H15C—C15'—H15D | 108.8 |
C11—C10—C9 | 111.1 (2) | C15'—C16'—C17' | 116.0 (19) |
C11—C10—H10A | 109.4 | C15'—C16'—H16C | 108.3 |
C9—C10—H10A | 109.4 | C17'—C16'—H16C | 108.3 |
C11—C10—H10B | 109.4 | C15'—C16'—H16D | 108.3 |
C9—C10—H10B | 109.4 | C17'—C16'—H16D | 108.3 |
H10A—C10—H10B | 108.0 | H16C—C16'—H16D | 107.4 |
N2—C11—C10 | 111.2 (2) | C12'—C17'—C16' | 114.7 (17) |
N2—C11—H11A | 109.4 | C12'—C17'—H17C | 108.6 |
C10—C11—H11A | 109.4 | C16'—C17'—H17C | 108.6 |
N2—C11—H11B | 109.4 | C12'—C17'—H17D | 108.6 |
C10—C11—H11B | 109.4 | C16'—C17'—H17D | 108.6 |
H11A—C11—H11B | 108.0 | H17C—C17'—H17D | 107.6 |
O1—Zn1—N1—C8 | 12.3 (2) | Zn1—N1—C9—C10 | −76.9 (3) |
Cl1—Zn1—N1—C8 | 126.07 (19) | N1—C9—C10—C11 | 174.6 (2) |
Cl2—Zn1—N1—C8 | −103.62 (19) | C12—N2—C11—C10 | 173.3 (3) |
O1—Zn1—N1—C9 | −169.4 (2) | C12'—N2—C11—C10 | 177.9 (8) |
Cl1—Zn1—N1—C9 | −55.7 (2) | C9—C10—C11—N2 | −178.9 (2) |
Cl2—Zn1—N1—C9 | 74.62 (19) | C11—N2—C12—C17 | −60.0 (6) |
N1—Zn1—O1—C1 | −18.3 (3) | C12'—N2—C12—C17 | −72 (3) |
Cl1—Zn1—O1—C1 | −136.7 (3) | C11—N2—C12—C13 | 63.9 (5) |
Cl2—Zn1—O1—C1 | 96.1 (3) | C12'—N2—C12—C13 | 52 (2) |
Zn1—O1—C1—C6 | 12.9 (5) | C17—C12—C13—C14 | −59.7 (7) |
Zn1—O1—C1—C2 | −168.4 (3) | N2—C12—C13—C14 | 176.9 (4) |
O1—C1—C2—C3 | 177.8 (4) | C12—C13—C14—C15 | 58.6 (6) |
C6—C1—C2—C3 | −3.4 (6) | C13—C14—C15—C16 | −61.1 (8) |
O1—C1—C2—C7 | −1.3 (6) | C14—C15—C16—C17 | 61.8 (10) |
C6—C1—C2—C7 | 177.5 (4) | N2—C12—C17—C16 | −177.6 (6) |
C1—C2—C3—C4 | 0.9 (8) | C13—C12—C17—C16 | 59.9 (9) |
C7—C2—C3—C4 | 179.9 (5) | C15—C16—C17—C12 | −59.4 (11) |
C2—C3—C4—C5 | 1.1 (10) | C11—N2—C12'—C17' | −79.8 (16) |
C3—C4—C5—C6 | −0.5 (9) | C12—N2—C12'—C17' | 90 (3) |
C4—C5—C6—C1 | −2.1 (7) | C11—N2—C12'—C13' | 159.3 (14) |
C4—C5—C6—C8 | 177.2 (5) | C12—N2—C12'—C13' | −31.0 (16) |
O1—C1—C6—C5 | −177.3 (4) | N2—C12'—C13'—C14' | 175.0 (16) |
C2—C1—C6—C5 | 4.0 (5) | C17'—C12'—C13'—C14' | 49 (2) |
O1—C1—C6—C8 | 3.5 (6) | C12'—C13'—C14'—C15' | −58 (3) |
C2—C1—C6—C8 | −175.2 (3) | C13'—C14'—C15'—C16' | 56 (2) |
C9—N1—C8—C6 | −179.8 (3) | C14'—C15'—C16'—C17' | −58 (3) |
Zn1—N1—C8—C6 | −1.5 (4) | N2—C12'—C17'—C16' | −170.7 (17) |
C5—C6—C8—N1 | 171.1 (3) | C13'—C12'—C17'—C16' | −46 (3) |
C1—C6—C8—N1 | −9.6 (5) | C15'—C16'—C17'—C12' | 56 (3) |
C8—N1—C9—C10 | 101.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1i | 0.90 | 2.35 | 3.254 (3) | 177 |
N2—H2B···Cl2ii | 0.90 | 2.44 | 3.325 (2) | 167 |
Symmetry codes: (i) −x+3/2, −y+5/2, −z+2; (ii) −x+3/2, −y+3/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C17H26N2O)] |
Mr | 410.67 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 35.492 (3), 7.482 (1), 15.011 (1) |
β (°) | 109.132 (1) |
V (Å3) | 3766.0 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.59 |
Crystal size (mm) | 0.25 × 0.24 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.692, 0.820 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15865, 4483, 3472 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.115, 1.04 |
No. of reflections | 4483 |
No. of parameters | 264 |
No. of restraints | 86 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.29 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
Zn1—O1 | 1.915 (2) | Zn1—Cl1 | 2.2373 (8) |
Zn1—N1 | 2.007 (2) | Zn1—Cl2 | 2.2606 (8) |
O1—Zn1—N1 | 96.43 (9) | O1—Zn1—Cl2 | 111.78 (8) |
O1—Zn1—Cl1 | 108.55 (8) | N1—Zn1—Cl2 | 109.86 (6) |
N1—Zn1—Cl1 | 114.37 (7) | Cl1—Zn1—Cl2 | 114.46 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1i | 0.90 | 2.35 | 3.254 (3) | 177 |
N2—H2B···Cl2ii | 0.90 | 2.44 | 3.325 (2) | 167 |
Symmetry codes: (i) −x+3/2, −y+5/2, −z+2; (ii) −x+3/2, −y+3/2, −z+2. |
The crystal structures of a few Schiff base zinc(II) compounds have been reported (You, 2005a,b,c). As an extension of the work on these compounds, the title zinc(II) compound, (I), is reported here.
Complex (I) is a mononuclear zinc(II) compound (Fig. 1). The ZnII atom is four-coordinated by one imine N and one phenolate O atoms from a Schiff base ligand, and by two terminal Cl atoms, forming a tetrahedral coordination. The Zn—N and Zn—O bond lengths and angles (Table 1) subtended at the Zn1 atom are comparable to the values observed in the Schiff base zinc(II) complexes cited above. As expected, the cyclohexyl group adopts a chair conformation to minimize steric effects.
In the crystal structure, molecules are linked through intermolecular N—H···Cl hydrogen bonds, forming chains running along the b axis (Fig. 2 and Table 2).