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
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.090
- Data-to-parameter ratio = 29.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.77 mm
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.928 Tmax scaled 0.928 Tmin scaled 0.757 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 32.20 From the CIF: _reflns_number_total 4979 Count of symmetry unique reflns 3029 Completeness (_total/calc) 164.38% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1950 Fraction of Friedel pairs measured 0.644 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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. |