Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113026267/cu3034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113026267/cu3034Isup2.hkl |
CCDC reference: 962782
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008).
(C10H22N2)[ZnCl4] | F(000) = 1552 |
Mr = 377.47 | Dx = 1.604 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9435 reflections |
a = 11.3673 (2) Å | θ = 3.1–76.4° |
b = 9.5997 (2) Å | µ = 8.30 mm−1 |
c = 28.6571 (5) Å | T = 110 K |
V = 3127.14 (10) Å3 | Prism, colourless |
Z = 8 | 0.26 × 0.22 × 0.15 mm |
Agilent SuperNova Dual diffractometer (Cu at zero) with Atlas detector | 3263 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3154 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.4508 pixels mm-1 | θmax = 76.2°, θmin = 3.1° |
ω scans | h = −14→10 |
Absorption correction: analytical [CrysAlisPro (Agilent, 2012); analytical numerical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] | k = −11→12 |
Tmin = 0.201, Tmax = 0.425 | l = −36→35 |
17184 measured reflections |
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)] = 0.022 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0273P)2 + 2.021P] where P = (Fo2 + 2Fc2)/3 |
3263 reflections | (Δ/σ)max = 0.001 |
166 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) |
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 | ||
Zn1 | 0.552127 (17) | 0.837964 (19) | 0.089690 (6) | 0.01164 (7) | |
Cl3 | 0.44251 (3) | 0.99531 (4) | 0.130948 (12) | 0.01701 (9) | |
Cl2 | 0.66233 (3) | 0.69395 (4) | 0.133374 (12) | 0.01658 (8) | |
Cl1 | 0.41865 (3) | 0.68822 (3) | 0.053615 (12) | 0.01533 (8) | |
Cl4 | 0.64732 (3) | 0.95295 (3) | 0.031959 (12) | 0.01565 (8) | |
N1 | 0.46089 (11) | 0.42781 (13) | 0.12379 (4) | 0.0116 (2) | |
N4 | 0.48467 (11) | 0.22977 (13) | 0.04818 (4) | 0.0136 (2) | |
C7 | 0.44402 (12) | 0.46430 (15) | 0.17543 (5) | 0.0129 (3) | |
H7 | 0.5235 | 0.4855 | 0.1885 | 0.015* | |
C3 | 0.59015 (13) | 0.30339 (16) | 0.06715 (5) | 0.0150 (3) | |
H3B | 0.6052 | 0.3888 | 0.0487 | 0.018* | |
H3A | 0.6600 | 0.2423 | 0.0645 | 0.018* | |
C6 | 0.35583 (13) | 0.35838 (15) | 0.10184 (5) | 0.0141 (3) | |
H6B | 0.2873 | 0.4218 | 0.1036 | 0.017* | |
H6A | 0.3364 | 0.2728 | 0.1195 | 0.017* | |
C2 | 0.57029 (13) | 0.34155 (15) | 0.11769 (5) | 0.0142 (3) | |
H2A | 0.5633 | 0.2554 | 0.1365 | 0.017* | |
H2B | 0.6390 | 0.3945 | 0.1294 | 0.017* | |
C12 | 0.39402 (15) | 0.34274 (16) | 0.20329 (5) | 0.0186 (3) | |
H12B | 0.4429 | 0.2587 | 0.1983 | 0.022* | |
H12A | 0.3130 | 0.3219 | 0.1926 | 0.022* | |
C9 | 0.36831 (15) | 0.63142 (17) | 0.23370 (5) | 0.0202 (3) | |
H9B | 0.4494 | 0.6538 | 0.2438 | 0.024* | |
H9A | 0.3192 | 0.7153 | 0.2386 | 0.024* | |
C5 | 0.37872 (13) | 0.32076 (15) | 0.05119 (5) | 0.0145 (3) | |
H5A | 0.3097 | 0.2714 | 0.0382 | 0.017* | |
H5B | 0.3915 | 0.4066 | 0.0327 | 0.017* | |
C8 | 0.36894 (13) | 0.59428 (16) | 0.18160 (5) | 0.0164 (3) | |
H8A | 0.2877 | 0.5765 | 0.1706 | 0.020* | |
H8B | 0.4021 | 0.6722 | 0.1632 | 0.020* | |
C11 | 0.39285 (16) | 0.38115 (18) | 0.25525 (5) | 0.0232 (3) | |
H11A | 0.3588 | 0.3033 | 0.2735 | 0.028* | |
H11B | 0.4745 | 0.3963 | 0.2662 | 0.028* | |
C10 | 0.32078 (16) | 0.51264 (18) | 0.26348 (6) | 0.0244 (3) | |
H10B | 0.3246 | 0.5388 | 0.2969 | 0.029* | |
H10A | 0.2374 | 0.4950 | 0.2554 | 0.029* | |
H4B | 0.4965 (18) | 0.205 (2) | 0.0185 (8) | 0.021 (5)* | |
H1 | 0.4747 (17) | 0.508 (2) | 0.1084 (7) | 0.016 (5)* | |
H4A | 0.4746 (19) | 0.150 (2) | 0.0639 (8) | 0.022 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01350 (11) | 0.00970 (11) | 0.01171 (11) | 0.00094 (7) | 0.00004 (7) | 0.00002 (6) |
Cl3 | 0.01859 (18) | 0.01404 (17) | 0.01840 (17) | 0.00101 (13) | 0.00349 (12) | −0.00108 (12) |
Cl2 | 0.01603 (17) | 0.01697 (16) | 0.01674 (17) | −0.00007 (13) | −0.00065 (12) | 0.00320 (12) |
Cl1 | 0.01766 (17) | 0.01406 (16) | 0.01426 (16) | −0.00266 (13) | −0.00250 (12) | 0.00128 (11) |
Cl4 | 0.01613 (16) | 0.01425 (16) | 0.01657 (16) | 0.00047 (12) | 0.00054 (12) | 0.00002 (12) |
N1 | 0.0128 (6) | 0.0115 (5) | 0.0106 (5) | 0.0003 (5) | 0.0005 (4) | −0.0002 (4) |
N4 | 0.0149 (6) | 0.0134 (6) | 0.0126 (6) | 0.0000 (5) | 0.0003 (5) | −0.0024 (5) |
C7 | 0.0149 (7) | 0.0140 (7) | 0.0097 (6) | 0.0006 (5) | −0.0007 (5) | −0.0022 (5) |
C3 | 0.0117 (7) | 0.0169 (7) | 0.0164 (7) | −0.0016 (6) | 0.0021 (5) | −0.0024 (5) |
C6 | 0.0117 (6) | 0.0160 (7) | 0.0147 (7) | 0.0002 (5) | −0.0013 (5) | −0.0018 (5) |
C2 | 0.0126 (7) | 0.0144 (7) | 0.0154 (7) | 0.0021 (5) | −0.0007 (5) | −0.0023 (5) |
C12 | 0.0274 (8) | 0.0165 (7) | 0.0119 (7) | −0.0010 (6) | 0.0014 (6) | 0.0007 (5) |
C9 | 0.0237 (8) | 0.0202 (7) | 0.0168 (7) | 0.0049 (6) | −0.0013 (6) | −0.0059 (6) |
C5 | 0.0138 (7) | 0.0159 (7) | 0.0137 (7) | 0.0015 (6) | −0.0017 (5) | −0.0014 (5) |
C8 | 0.0191 (7) | 0.0156 (7) | 0.0146 (7) | 0.0022 (6) | 0.0000 (5) | −0.0009 (5) |
C11 | 0.0345 (9) | 0.0237 (8) | 0.0116 (7) | −0.0002 (7) | 0.0019 (6) | 0.0013 (6) |
C10 | 0.0277 (8) | 0.0319 (9) | 0.0134 (7) | 0.0028 (7) | 0.0042 (6) | −0.0037 (6) |
Zn1—Cl2 | 2.2467 (4) | C6—H6A | 0.9900 |
Zn1—Cl4 | 2.2641 (4) | C2—H2A | 0.9900 |
Zn1—Cl3 | 2.2874 (4) | C2—H2B | 0.9900 |
Zn1—Cl1 | 2.3318 (4) | C12—C11 | 1.534 (2) |
N1—C2 | 1.5043 (18) | C12—H12B | 0.9900 |
N1—C6 | 1.5052 (18) | C12—H12A | 0.9900 |
N1—C7 | 1.5328 (17) | C9—C10 | 1.523 (2) |
N1—H1 | 0.90 (2) | C9—C8 | 1.535 (2) |
N4—C5 | 1.4902 (19) | C9—H9B | 0.9900 |
N4—C3 | 1.4942 (18) | C9—H9A | 0.9900 |
N4—H4B | 0.89 (2) | C5—H5A | 0.9900 |
N4—H4A | 0.90 (2) | C5—H5B | 0.9900 |
C7—C8 | 1.522 (2) | C8—H8A | 0.9900 |
C7—C12 | 1.524 (2) | C8—H8B | 0.9900 |
C7—H7 | 1.0000 | C11—C10 | 1.523 (2) |
C3—C2 | 1.511 (2) | C11—H11A | 0.9900 |
C3—H3B | 0.9900 | C11—H11B | 0.9900 |
C3—H3A | 0.9900 | C10—H10B | 0.9900 |
C6—C5 | 1.5183 (19) | C10—H10A | 0.9900 |
C6—H6B | 0.9900 | ||
Cl2—Zn1—Cl4 | 116.146 (15) | N1—C2—H2B | 109.3 |
Cl2—Zn1—Cl3 | 114.966 (15) | C3—C2—H2B | 109.3 |
Cl4—Zn1—Cl3 | 108.429 (14) | H2A—C2—H2B | 108.0 |
Cl2—Zn1—Cl1 | 103.327 (14) | C7—C12—C11 | 109.13 (13) |
Cl4—Zn1—Cl1 | 106.711 (14) | C7—C12—H12B | 109.9 |
Cl3—Zn1—Cl1 | 106.366 (15) | C11—C12—H12B | 109.9 |
C2—N1—C6 | 111.32 (11) | C7—C12—H12A | 109.9 |
C2—N1—C7 | 109.96 (11) | C11—C12—H12A | 109.9 |
C6—N1—C7 | 113.91 (11) | H12B—C12—H12A | 108.3 |
C2—N1—H1 | 105.6 (13) | C10—C9—C8 | 111.88 (13) |
C6—N1—H1 | 108.1 (13) | C10—C9—H9B | 109.2 |
C7—N1—H1 | 107.5 (12) | C8—C9—H9B | 109.2 |
C5—N4—C3 | 110.50 (11) | C10—C9—H9A | 109.2 |
C5—N4—H4B | 109.3 (13) | C8—C9—H9A | 109.2 |
C3—N4—H4B | 110.5 (13) | H9B—C9—H9A | 107.9 |
C5—N4—H4A | 111.6 (14) | N4—C5—C6 | 109.47 (11) |
C3—N4—H4A | 108.9 (14) | N4—C5—H5A | 109.8 |
H4B—N4—H4A | 105.9 (18) | C6—C5—H5A | 109.8 |
C8—C7—C12 | 110.96 (12) | N4—C5—H5B | 109.8 |
C8—C7—N1 | 111.70 (11) | C6—C5—H5B | 109.8 |
C12—C7—N1 | 112.18 (12) | H5A—C5—H5B | 108.2 |
C8—C7—H7 | 107.2 | C7—C8—C9 | 107.83 (12) |
C12—C7—H7 | 107.2 | C7—C8—H8A | 110.1 |
N1—C7—H7 | 107.2 | C9—C8—H8A | 110.1 |
N4—C3—C2 | 110.09 (12) | C7—C8—H8B | 110.1 |
N4—C3—H3B | 109.6 | C9—C8—H8B | 110.1 |
C2—C3—H3B | 109.6 | H8A—C8—H8B | 108.5 |
N4—C3—H3A | 109.6 | C10—C11—C12 | 110.74 (13) |
C2—C3—H3A | 109.6 | C10—C11—H11A | 109.5 |
H3B—C3—H3A | 108.2 | C12—C11—H11A | 109.5 |
N1—C6—C5 | 111.64 (12) | C10—C11—H11B | 109.5 |
N1—C6—H6B | 109.3 | C12—C11—H11B | 109.5 |
C5—C6—H6B | 109.3 | H11A—C11—H11B | 108.1 |
N1—C6—H6A | 109.3 | C11—C10—C9 | 110.05 (13) |
C5—C6—H6A | 109.3 | C11—C10—H10B | 109.7 |
H6B—C6—H6A | 108.0 | C9—C10—H10B | 109.7 |
N1—C2—C3 | 111.61 (12) | C11—C10—H10A | 109.7 |
N1—C2—H2A | 109.3 | C9—C10—H10A | 109.7 |
C3—C2—H2A | 109.3 | H10B—C10—H10A | 108.2 |
C2—N1—C7—C8 | 156.71 (12) | C8—C7—C12—C11 | −60.68 (17) |
C6—N1—C7—C8 | −77.55 (15) | N1—C7—C12—C11 | 173.60 (12) |
C2—N1—C7—C12 | −77.98 (14) | C3—N4—C5—C6 | −60.15 (15) |
C6—N1—C7—C12 | 47.76 (16) | N1—C6—C5—N4 | 56.76 (15) |
C5—N4—C3—C2 | 60.08 (15) | C12—C7—C8—C9 | 60.11 (16) |
C2—N1—C6—C5 | −53.28 (15) | N1—C7—C8—C9 | −173.91 (12) |
C7—N1—C6—C5 | −178.30 (11) | C10—C9—C8—C7 | −58.33 (17) |
C6—N1—C2—C3 | 52.84 (15) | C7—C12—C11—C10 | 57.94 (18) |
C7—N1—C2—C3 | −179.96 (11) | C12—C11—C10—C9 | −56.23 (18) |
N4—C3—C2—N1 | −56.07 (16) | C8—C9—C10—C11 | 57.11 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.90 (2) | 2.42 (2) | 3.2441 (13) | 152 (2) |
N4—H4A···Cl3i | 0.90 (2) | 2.46 (2) | 3.3050 (12) | 158 (2) |
C5—H5A···Cl1ii | 0.99 | 2.75 | 3.6125 (15) | 146 |
N4—H4B···Cl1iii | 0.89 (2) | 2.50 (2) | 3.2153 (12) | 138 (2) |
N4—H4B···Cl4iii | 0.89 (2) | 2.66 (2) | 3.2561 (12) | 125 (2) |
C5—H5B···Cl1 | 0.99 | 2.79 | 3.5573 (15) | 135 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, z; (iii) −x+1, −y+1, −z. |