Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008409/om2105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008409/om2105Isup2.hkl |
CCDC reference: 640438
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H26Cl2 | F(000) = 600 |
Mr = 277.26 | Dx = 1.221 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5072 reflections |
a = 6.0259 (4) Å | θ = 2.7–32.1° |
b = 15.6356 (9) Å | µ = 0.41 mm−1 |
c = 16.0117 (11) Å | T = 180 K |
V = 1508.60 (17) Å3 | Needle, colorless |
Z = 4 | 0.77 × 0.28 × 0.18 mm |
Oxford Diffraction CCD Xcalibur diffractometer | 4979 independent reflections |
Radiation source: fine-focus sealed tube | 4123 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.2632 pixels mm-1 | θmax = 32.2°, θmin = 2.9° |
ω and φ scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −22→23 |
Tmin = 0.816, Tmax = 1.0 | l = −21→23 |
16088 measured reflections |
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)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4601 reflections | Δρmax = 0.29 e Å−3 |
158 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1963 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (5) |
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. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3) (p.p.m.): 1.61, 1.63 (3H12, 3H13, 2 s), 0.85, 0.97 (3H14, 3H15, 2 s); 13 C NMR (CDCl3) (p.p.m.): 43.8 (C-1), 51.1 (C-2), 72.7 (C-3), 46.2 (C-4), 33.1 (C-5), 44.1 (C-6), 76.9 (C-7), 35.7 (C-8), 21.5 (C-9), 34.6 (C-10), 36.3 (C-11), 41.5 (C-12), 40.7 (C-13), 22.5 (C-14), 26.5 (C-15). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4376 (2) | 0.00470 (8) | 0.54846 (7) | 0.0183 (2) | |
H1 | 0.2720 | 0.0034 | 0.5448 | 0.022* | |
C2 | 0.4958 (2) | 0.05331 (8) | 0.62985 (8) | 0.0210 (2) | |
H2A | 0.4383 | 0.0199 | 0.6777 | 0.025* | |
H2B | 0.6594 | 0.0553 | 0.6352 | 0.025* | |
C3 | 0.4075 (2) | 0.14424 (8) | 0.63694 (9) | 0.0228 (2) | |
C4 | 0.4732 (3) | 0.19491 (9) | 0.56003 (9) | 0.0263 (3) | |
H4A | 0.3956 | 0.2507 | 0.5609 | 0.032* | |
H4B | 0.6348 | 0.2063 | 0.5620 | 0.032* | |
C5 | 0.4186 (3) | 0.14916 (9) | 0.47923 (9) | 0.0267 (3) | |
H5A | 0.4731 | 0.1840 | 0.4319 | 0.032* | |
H5B | 0.2553 | 0.1447 | 0.4740 | 0.032* | |
C6 | 0.5201 (2) | 0.05845 (9) | 0.47274 (8) | 0.0208 (3) | |
H6 | 0.6838 | 0.0655 | 0.4803 | 0.025* | |
C7 | 0.4864 (3) | 0.02318 (10) | 0.38266 (8) | 0.0264 (3) | |
C8 | 0.6097 (3) | −0.06061 (10) | 0.36414 (10) | 0.0329 (3) | |
H81 | 0.6152 | −0.0670 | 0.3027 | 0.039* | |
H82 | 0.7646 | −0.0530 | 0.3834 | 0.039* | |
C9 | 0.5278 (3) | −0.14502 (11) | 0.39947 (10) | 0.0373 (4) | |
H91 | 0.6563 | −0.1844 | 0.4021 | 0.045* | |
H92 | 0.4215 | −0.1695 | 0.3589 | 0.045* | |
C10 | 0.4161 (3) | −0.14574 (9) | 0.48528 (9) | 0.0315 (3) | |
H101 | 0.4121 | −0.2058 | 0.5048 | 0.038* | |
H102 | 0.2602 | −0.1274 | 0.4774 | 0.038* | |
C11 | 0.5156 (3) | −0.09102 (9) | 0.55648 (9) | 0.0250 (3) | |
C12 | 0.4811 (3) | 0.18776 (10) | 0.71715 (10) | 0.0340 (4) | |
H121 | 0.4299 | 0.1543 | 0.7652 | 0.051* | |
H122 | 0.4174 | 0.2454 | 0.7198 | 0.051* | |
H123 | 0.6434 | 0.1916 | 0.7182 | 0.051* | |
C13 | 0.5603 (3) | 0.08826 (13) | 0.31648 (10) | 0.0429 (4) | |
H131 | 0.7157 | 0.1038 | 0.3261 | 0.064* | |
H132 | 0.4674 | 0.1396 | 0.3204 | 0.064* | |
H133 | 0.5448 | 0.0630 | 0.2608 | 0.064* | |
C14 | 0.4182 (3) | −0.12981 (9) | 0.63686 (11) | 0.0387 (4) | |
H141 | 0.4430 | −0.1918 | 0.6370 | 0.058* | |
H142 | 0.2585 | −0.1182 | 0.6392 | 0.058* | |
H143 | 0.4910 | −0.1042 | 0.6855 | 0.058* | |
C15 | 0.7694 (3) | −0.09965 (11) | 0.56065 (11) | 0.0362 (4) | |
H151 | 0.8248 | −0.0705 | 0.6107 | 0.054* | |
H152 | 0.8356 | −0.0736 | 0.5109 | 0.054* | |
H153 | 0.8097 | −0.1603 | 0.5631 | 0.054* | |
Cl3 | 0.10164 (6) | 0.13898 (2) | 0.64072 (3) | 0.03430 (10) | |
Cl7 | 0.18821 (6) | 0.00626 (3) | 0.36419 (3) | 0.03478 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0172 (6) | 0.0184 (5) | 0.0193 (5) | 0.0016 (5) | −0.0016 (4) | 0.0001 (5) |
C2 | 0.0231 (6) | 0.0194 (5) | 0.0206 (6) | 0.0016 (5) | −0.0019 (6) | 0.0000 (5) |
C3 | 0.0214 (6) | 0.0211 (5) | 0.0260 (6) | 0.0000 (5) | 0.0020 (6) | −0.0011 (6) |
C4 | 0.0298 (8) | 0.0193 (6) | 0.0297 (7) | −0.0025 (6) | 0.0026 (6) | 0.0016 (5) |
C5 | 0.0327 (8) | 0.0220 (6) | 0.0252 (7) | 0.0031 (6) | 0.0012 (6) | 0.0073 (5) |
C6 | 0.0173 (6) | 0.0254 (6) | 0.0197 (6) | −0.0003 (5) | −0.0001 (5) | 0.0026 (5) |
C7 | 0.0193 (6) | 0.0389 (8) | 0.0211 (6) | −0.0005 (6) | 0.0010 (5) | 0.0018 (5) |
C8 | 0.0271 (7) | 0.0462 (8) | 0.0254 (7) | 0.0042 (7) | 0.0023 (7) | −0.0084 (7) |
C9 | 0.0426 (9) | 0.0363 (8) | 0.0328 (8) | 0.0079 (8) | −0.0060 (7) | −0.0125 (7) |
C10 | 0.0368 (8) | 0.0237 (7) | 0.0341 (8) | −0.0001 (7) | −0.0066 (6) | −0.0053 (6) |
C11 | 0.0321 (8) | 0.0180 (6) | 0.0248 (6) | 0.0025 (5) | −0.0047 (6) | −0.0018 (5) |
C12 | 0.0422 (10) | 0.0290 (8) | 0.0309 (8) | 0.0026 (7) | −0.0032 (7) | −0.0092 (6) |
C13 | 0.0504 (11) | 0.0565 (11) | 0.0217 (7) | −0.0051 (9) | 0.0077 (7) | 0.0087 (7) |
C14 | 0.0639 (11) | 0.0226 (6) | 0.0298 (7) | −0.0018 (7) | −0.0052 (9) | 0.0081 (6) |
C15 | 0.0360 (9) | 0.0327 (8) | 0.0399 (9) | 0.0139 (7) | −0.0127 (7) | −0.0083 (7) |
Cl3 | 0.02332 (16) | 0.03535 (18) | 0.0442 (2) | 0.00334 (14) | 0.00712 (17) | −0.00121 (17) |
Cl7 | 0.02419 (16) | 0.0494 (2) | 0.03075 (17) | 0.00076 (16) | −0.00922 (14) | −0.00253 (18) |
C1—C2 | 1.5489 (17) | C8—H81 | 0.9900 |
C1—C6 | 1.5566 (18) | C8—H82 | 0.9900 |
C1—C11 | 1.5739 (19) | C9—C10 | 1.530 (2) |
C1—H1 | 1.0000 | C9—H91 | 0.9900 |
C2—C3 | 1.5224 (17) | C9—H92 | 0.9900 |
C2—H2A | 0.9900 | C10—C11 | 1.547 (2) |
C2—H2B | 0.9900 | C10—H101 | 0.9900 |
C3—C4 | 1.5170 (19) | C10—H102 | 0.9900 |
C3—C12 | 1.520 (2) | C11—C15 | 1.537 (2) |
C3—Cl3 | 1.8459 (14) | C11—C14 | 1.539 (2) |
C4—C5 | 1.515 (2) | C12—H121 | 0.9800 |
C4—H4A | 0.9900 | C12—H122 | 0.9800 |
C4—H4B | 0.9900 | C12—H123 | 0.9800 |
C5—C6 | 1.5481 (19) | C13—H131 | 0.9800 |
C5—H5A | 0.9900 | C13—H132 | 0.9800 |
C5—H5B | 0.9900 | C13—H133 | 0.9800 |
C6—C7 | 1.5573 (19) | C14—H141 | 0.9800 |
C6—H6 | 1.0000 | C14—H142 | 0.9800 |
C7—C8 | 1.535 (2) | C14—H143 | 0.9800 |
C7—C13 | 1.535 (2) | C15—H151 | 0.9800 |
C7—Cl7 | 1.8403 (15) | C15—H152 | 0.9800 |
C8—C9 | 1.518 (2) | C15—H153 | 0.9800 |
C2—C1—C6 | 108.55 (10) | C9—C8—H82 | 107.1 |
C2—C1—C11 | 109.29 (10) | C7—C8—H82 | 107.1 |
C6—C1—C11 | 118.80 (11) | H81—C8—H82 | 106.8 |
C2—C1—H1 | 106.5 | C8—C9—C10 | 118.94 (13) |
C6—C1—H1 | 106.5 | C8—C9—H91 | 107.6 |
C11—C1—H1 | 106.5 | C10—C9—H91 | 107.6 |
C3—C2—C1 | 116.23 (11) | C8—C9—H92 | 107.6 |
C3—C2—H2A | 108.2 | C10—C9—H92 | 107.6 |
C1—C2—H2A | 108.2 | H91—C9—H92 | 107.0 |
C3—C2—H2B | 108.2 | C9—C10—C11 | 119.15 (14) |
C1—C2—H2B | 108.2 | C9—C10—H101 | 107.5 |
H2A—C2—H2B | 107.4 | C11—C10—H101 | 107.5 |
C4—C3—C12 | 112.09 (11) | C9—C10—H102 | 107.5 |
C4—C3—C2 | 109.63 (11) | C11—C10—H102 | 107.5 |
C12—C3—C2 | 112.29 (12) | H101—C10—H102 | 107.0 |
C4—C3—Cl3 | 108.09 (10) | C15—C11—C14 | 107.99 (14) |
C12—C3—Cl3 | 106.47 (10) | C15—C11—C10 | 111.68 (13) |
C2—C3—Cl3 | 108.05 (9) | C14—C11—C10 | 104.50 (12) |
C5—C4—C3 | 112.95 (12) | C15—C11—C1 | 112.60 (12) |
C5—C4—H4A | 109.0 | C14—C11—C1 | 109.21 (12) |
C3—C4—H4A | 109.0 | C10—C11—C1 | 110.49 (11) |
C5—C4—H4B | 109.0 | C3—C12—H121 | 109.5 |
C3—C4—H4B | 109.0 | C3—C12—H122 | 109.5 |
H4A—C4—H4B | 107.8 | H121—C12—H122 | 109.5 |
C4—C5—C6 | 113.84 (12) | C3—C12—H123 | 109.5 |
C4—C5—H5A | 108.8 | H121—C12—H123 | 109.5 |
C6—C5—H5A | 108.8 | H122—C12—H123 | 109.5 |
C4—C5—H5B | 108.8 | C7—C13—H131 | 109.5 |
C6—C5—H5B | 108.8 | C7—C13—H132 | 109.5 |
H5A—C5—H5B | 107.7 | H131—C13—H132 | 109.5 |
C5—C6—C1 | 108.44 (11) | C7—C13—H133 | 109.5 |
C5—C6—C7 | 109.58 (11) | H131—C13—H133 | 109.5 |
C1—C6—C7 | 119.25 (11) | H132—C13—H133 | 109.5 |
C5—C6—H6 | 106.3 | C11—C14—H141 | 109.5 |
C1—C6—H6 | 106.3 | C11—C14—H142 | 109.5 |
C7—C6—H6 | 106.3 | H141—C14—H142 | 109.5 |
C8—C7—C13 | 106.99 (13) | C11—C14—H143 | 109.5 |
C8—C7—C6 | 114.72 (12) | H141—C14—H143 | 109.5 |
C13—C7—C6 | 111.52 (13) | H142—C14—H143 | 109.5 |
C8—C7—Cl7 | 108.58 (10) | C11—C15—H151 | 109.5 |
C13—C7—Cl7 | 105.51 (11) | C11—C15—H152 | 109.5 |
C6—C7—Cl7 | 109.08 (10) | H151—C15—H152 | 109.5 |
C9—C8—C7 | 120.86 (13) | C11—C15—H153 | 109.5 |
C9—C8—H81 | 107.1 | H151—C15—H153 | 109.5 |
C7—C8—H81 | 107.1 | H152—C15—H153 | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H82···Cl7i | 0.99 | 2.73 | 3.6397 (16) | 152 |
Symmetry code: (i) x+1, y, z. |