Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805036706/bt6776sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805036706/bt6776Isup2.hkl |
CCDC reference: 293833
Data collection: COLLECT (Nonius, 2003); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Version 2.1; Bergerhoff et al., 1997); software used to prepare material for publication: SHELXL97.
C16H18 | F(000) = 228 |
Mr = 210.30 | Dx = 1.090 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.787 (1) Å | Cell parameters from 12888 reflections |
b = 8.776 (2) Å | θ = 26.6–1288° |
c = 12.617 (3) Å | µ = 0.06 mm−1 |
β = 91.25 (3)° | T = 293 K |
V = 640.6 (2) Å3 | Prism, colourless |
Z = 2 | 0.10 × 0.06 × 0.05 mm |
Nonius KappaCCD diffractometer | 1464 independent reflections |
Radiation source: fine-focus sealed tube | 1139 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
φ and ω scans | h = −7→7 |
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997 | k = −11→11 |
Tmin = 0.994, Tmax = 0.997 | l = −16→16 |
2835 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)] = 0.048 | All H-atom parameters refined |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0749P)2 + 0.0552P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
1464 reflections | Δρmax = 0.11 e Å−3 |
110 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.09 (3) |
Experimental. Single-crystal X-ray intensity data were collected at 293 K on a Nonius Kappa diffractometer with CCD-area detector, using 805 frames with phi- and omega-increments of 1.5 degrees and a counting time of 12 s per frame. The crystal- to-detector-distance was 34 mm. The whole ewald sphere was measured. The reflection data were processed with the Nonius program suite DENZO-SMN and corrected for Lorentz, polarization, background and absorption effects (Otwinowski and Minor, 1997). The crystal structure was determined by Direct methods (SHELXS97, Sheldrick, 1997) and subsequent Fourier and difference Fourier syntheses, followed by full-matrix least-squares refinements on F2 (SHELXL97, Sheldrick, 1997). All hydrogen atoms were refined freely. Using anisotropic treatment of the non-H atoms and unrestrained isotropic treatment of the H atoms, the refinement converged at R-values of 0.048. |
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 | ||
C6 | 0.8581 (2) | 0.15225 (13) | 0.71853 (9) | 0.0549 (4) | |
C1 | 0.8987 (3) | 0.07511 (16) | 0.81254 (11) | 0.0684 (4) | |
H1 | 1.031 (2) | 0.0078 (19) | 0.8194 (12) | 0.090 (5)* | |
C2 | 0.7520 (3) | 0.09114 (18) | 0.89703 (11) | 0.0756 (5) | |
H2 | 0.779 (3) | 0.034 (2) | 0.9597 (15) | 0.106 (5)* | |
C3 | 0.5644 (2) | 0.18631 (19) | 0.88904 (11) | 0.0740 (5) | |
H3 | 0.462 (3) | 0.1975 (19) | 0.9495 (15) | 0.092 (5)* | |
C4 | 0.5228 (3) | 0.26404 (19) | 0.79690 (11) | 0.0750 (5) | |
H4 | 0.392 (3) | 0.3338 (19) | 0.7899 (14) | 0.099 (5)* | |
C5 | 0.6680 (2) | 0.24721 (16) | 0.71236 (10) | 0.0646 (4) | |
H5 | 0.638 (3) | 0.3045 (19) | 0.6465 (14) | 0.093 (5)* | |
C7 | 1.0116 (3) | 0.13128 (18) | 0.62438 (11) | 0.0680 (4) | |
H71 | 1.026 (3) | 0.2277 (19) | 0.5840 (13) | 0.090 (5)* | |
H72 | 1.167 (3) | 0.1023 (19) | 0.6482 (13) | 0.089 (5)* | |
C8 | 0.9273 (2) | 0.00660 (14) | 0.54925 (9) | 0.0583 (4) | |
H81 | 1.073 (2) | 0.0921 (19) | 0.4129 (12) | 0.079 (4)* | |
H82 | 0.766 (2) | 0.0285 (16) | 0.5264 (11) | 0.074 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C6 | 0.0580 (7) | 0.0564 (7) | 0.0506 (6) | −0.0090 (5) | 0.0088 (5) | −0.0109 (5) |
C1 | 0.0741 (8) | 0.0664 (8) | 0.0647 (8) | 0.0096 (7) | 0.0042 (6) | −0.0030 (6) |
C2 | 0.0962 (11) | 0.0808 (10) | 0.0499 (7) | −0.0001 (8) | 0.0067 (7) | 0.0056 (6) |
C3 | 0.0746 (9) | 0.0950 (10) | 0.0531 (7) | −0.0032 (8) | 0.0170 (6) | −0.0123 (6) |
C4 | 0.0647 (8) | 0.0952 (11) | 0.0653 (8) | 0.0149 (7) | 0.0071 (6) | −0.0113 (7) |
C5 | 0.0688 (8) | 0.0740 (8) | 0.0512 (7) | 0.0029 (6) | 0.0042 (5) | −0.0005 (6) |
C7 | 0.0673 (8) | 0.0740 (9) | 0.0635 (8) | −0.0144 (7) | 0.0217 (6) | −0.0172 (6) |
C8 | 0.0629 (8) | 0.0590 (8) | 0.0539 (7) | −0.0077 (6) | 0.0188 (5) | −0.0073 (5) |
C6—C5 | 1.3810 (19) | C4—C5 | 1.3799 (19) |
C6—C1 | 1.3814 (19) | C4—H4 | 0.978 (17) |
C6—C7 | 1.5099 (16) | C5—H5 | 0.983 (18) |
C1—C2 | 1.384 (2) | C7—C8 | 1.5211 (17) |
C1—H1 | 0.968 (16) | C7—H71 | 0.992 (17) |
C2—C3 | 1.372 (2) | C7—H72 | 0.977 (16) |
C2—H2 | 0.946 (19) | C8—C8i | 1.520 (2) |
C3—C4 | 1.365 (2) | C8—H82 | 0.991 (14) |
C3—H3 | 0.981 (18) | ||
C5—C6—C1 | 117.67 (12) | C5—C4—H4 | 118.8 (11) |
C5—C6—C7 | 120.72 (12) | C4—C5—C6 | 121.24 (13) |
C1—C6—C7 | 121.60 (13) | C4—C5—H5 | 119.8 (10) |
C6—C1—C2 | 121.06 (13) | C6—C5—H5 | 118.9 (10) |
C6—C1—H1 | 119.7 (9) | C6—C7—C8 | 113.07 (10) |
C2—C1—H1 | 119.2 (9) | C6—C7—H71 | 111.0 (10) |
C3—C2—C1 | 120.19 (13) | C8—C7—H71 | 108.8 (10) |
C3—C2—H2 | 120.0 (11) | C6—C7—H72 | 110.1 (10) |
C1—C2—H2 | 119.8 (11) | C8—C7—H72 | 106.6 (10) |
C4—C3—C2 | 119.45 (13) | H71—C7—H72 | 107.0 (14) |
C4—C3—H3 | 120.9 (10) | C8i—C8—C7 | 112.86 (12) |
C2—C3—H3 | 119.6 (10) | C8i—C8—H82 | 108.2 (8) |
C3—C4—C5 | 120.39 (14) | C7—C8—H82 | 109.2 (8) |
C3—C4—H4 | 120.8 (11) |
Symmetry code: (i) −x+2, −y, −z+1. |