Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004725/cv6098sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004725/cv6098Isup2.hkl |
CCDC reference: 183811
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.124
- Data-to-parameter ratio = 13.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
CRYSR_01 Alert C _exptl_crystal_size_rad not in the CIF when expected. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1941 Count of symmetry unique reflns 1533 Completeness (_total/calc) 126.61% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 408 Fraction of Friedel pairs measured 0.266 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Siemens, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C16H26 | Dx = 0.999 Mg m−3 |
Mr = 218.37 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 95 reflections |
a = 5.1428 (16) Å | θ = 2.8–18.7° |
b = 8.908 (3) Å | µ = 0.06 mm−1 |
c = 31.687 (11) Å | T = 213 K |
V = 1451.7 (8) Å3 | Cylinder, colourless |
Z = 4 | 0.4 × 0.2 × 0.2 mm |
F(000) = 488 |
Bruker AXS CCD 1000 diffractometer | 1941 independent reflections |
Radiation source: fine-focus sealed tube | 1287 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | h = −2→7 |
Tmin = 0.970, Tmax = 0.991 | k = −10→11 |
6337 measured reflections | l = −33→37 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.1408P] where P = (Fo2 + 2Fc2)/3 |
1941 reflections | (Δ/σ)max = 0.002 |
145 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | ||
C12 | 0.8879 (5) | 0.4795 (2) | 0.97682 (6) | 0.0456 (5) | |
H12A | 0.9132 | 0.5678 | 0.9588 | 0.055* | |
H12B | 0.7002 | 0.4645 | 0.9801 | 0.055* | |
C10 | 0.8846 (5) | 0.3120 (2) | 0.91177 (6) | 0.0460 (5) | |
H10A | 0.9124 | 0.3997 | 0.8936 | 0.055* | |
H10B | 0.6966 | 0.2984 | 0.9150 | 0.055* | |
C14 | 0.8918 (4) | 0.6478 (2) | 1.04146 (6) | 0.0449 (5) | |
H14A | 0.9162 | 0.7354 | 1.0232 | 0.054* | |
H14B | 0.7043 | 0.6329 | 1.0451 | 0.054* | |
C11 | 1.0022 (4) | 0.3431 (2) | 0.95472 (6) | 0.0460 (5) | |
H11A | 1.1899 | 0.3581 | 0.9514 | 0.055* | |
H11B | 0.9768 | 0.2548 | 0.9727 | 0.055* | |
C13 | 1.0049 (4) | 0.5109 (2) | 1.01967 (6) | 0.0452 (5) | |
H13A | 1.1928 | 0.5251 | 1.0164 | 0.054* | |
H13B | 0.9782 | 0.4230 | 1.0378 | 0.054* | |
C8 | 0.8741 (4) | 0.1408 (2) | 0.84769 (6) | 0.0446 (5) | |
H8A | 0.9004 | 0.2272 | 0.8290 | 0.053* | |
H8B | 0.6864 | 0.1277 | 0.8516 | 0.053* | |
C9 | 0.9971 (4) | 0.1740 (2) | 0.89002 (6) | 0.0473 (5) | |
H9A | 1.1843 | 0.1888 | 0.8860 | 0.057* | |
H9B | 0.9737 | 0.0868 | 0.9085 | 0.057* | |
C15 | 1.0109 (5) | 0.6806 (2) | 1.08385 (7) | 0.0525 (6) | |
H15A | 1.1985 | 0.6949 | 1.0803 | 0.063* | |
H15B | 0.9853 | 0.5934 | 1.1022 | 0.063* | |
C1 | 0.8662 (4) | −0.0286 (2) | 0.78391 (6) | 0.0453 (5) | |
C16 | 0.8981 (6) | 0.8184 (3) | 1.10536 (7) | 0.0654 (7) | |
H16A | 0.9830 | 0.8331 | 1.1324 | 0.098* | |
H16B | 0.7130 | 0.8042 | 1.1097 | 0.098* | |
H16C | 0.9263 | 0.9058 | 1.0877 | 0.098* | |
C7 | 0.9847 (4) | 0.0006 (2) | 0.82643 (7) | 0.0556 (6) | |
H7A | 1.1731 | 0.0123 | 0.8232 | 0.067* | |
H7B | 0.9538 | −0.0864 | 0.8447 | 0.067* | |
C3 | 0.5427 (5) | −0.1466 (3) | 0.74008 (9) | 0.0661 (7) | |
H3A | 0.3990 | −0.2111 | 0.7374 | 0.079* | |
C2 | 0.6538 (5) | −0.1234 (3) | 0.77901 (8) | 0.0565 (6) | |
H2A | 0.5848 | −0.1726 | 0.8027 | 0.068* | |
C5 | 0.8497 (5) | 0.0174 (3) | 0.70955 (8) | 0.0655 (7) | |
H5A | 0.9171 | 0.0662 | 0.6856 | 0.079* | |
C6 | 0.9616 (5) | 0.0406 (3) | 0.74830 (8) | 0.0586 (6) | |
H6A | 1.1059 | 0.1049 | 0.7506 | 0.070* | |
C4 | 0.6412 (6) | −0.0762 (3) | 0.70546 (9) | 0.0666 (7) | |
H4A | 0.5657 | −0.0919 | 0.6788 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C12 | 0.0471 (11) | 0.0471 (12) | 0.0427 (12) | 0.0013 (10) | −0.0018 (10) | 0.0029 (10) |
C10 | 0.0488 (11) | 0.0475 (12) | 0.0417 (12) | 0.0025 (10) | −0.0021 (10) | 0.0032 (10) |
C14 | 0.0481 (11) | 0.0472 (12) | 0.0394 (12) | 0.0012 (10) | 0.0004 (10) | 0.0047 (10) |
C11 | 0.0475 (10) | 0.0479 (11) | 0.0425 (12) | −0.0005 (10) | −0.0021 (10) | 0.0021 (10) |
C13 | 0.0458 (11) | 0.0463 (12) | 0.0434 (13) | 0.0006 (10) | −0.0035 (10) | 0.0026 (10) |
C8 | 0.0452 (10) | 0.0480 (12) | 0.0406 (12) | 0.0029 (10) | −0.0003 (9) | 0.0025 (10) |
C9 | 0.0462 (10) | 0.0510 (13) | 0.0445 (13) | 0.0051 (10) | −0.0029 (10) | 0.0011 (10) |
C15 | 0.0627 (13) | 0.0520 (13) | 0.0429 (13) | −0.0006 (12) | −0.0016 (12) | 0.0019 (11) |
C1 | 0.0450 (10) | 0.0461 (11) | 0.0449 (13) | 0.0108 (10) | −0.0006 (10) | −0.0025 (10) |
C16 | 0.0881 (19) | 0.0601 (16) | 0.0479 (15) | −0.0008 (15) | 0.0045 (14) | −0.0050 (11) |
C7 | 0.0556 (12) | 0.0647 (15) | 0.0465 (14) | 0.0153 (12) | −0.0040 (11) | −0.0036 (12) |
C3 | 0.0572 (14) | 0.0635 (16) | 0.0777 (19) | −0.0034 (13) | −0.0145 (14) | −0.0076 (15) |
C2 | 0.0532 (12) | 0.0575 (14) | 0.0590 (16) | 0.0033 (12) | 0.0051 (12) | 0.0030 (12) |
C5 | 0.0704 (15) | 0.0778 (17) | 0.0484 (15) | 0.0054 (15) | 0.0001 (13) | 0.0053 (13) |
C6 | 0.0532 (12) | 0.0664 (15) | 0.0563 (15) | −0.0059 (12) | −0.0012 (11) | −0.0013 (12) |
C4 | 0.0704 (16) | 0.0701 (16) | 0.0594 (17) | 0.0132 (15) | −0.0152 (14) | −0.0114 (14) |
C12—C13 | 1.511 (3) | C9—H9B | 0.9800 |
C12—C11 | 1.521 (3) | C15—C16 | 1.519 (3) |
C12—H12A | 0.9800 | C15—H15A | 0.9800 |
C12—H12B | 0.9800 | C15—H15B | 0.9800 |
C10—C11 | 1.515 (3) | C1—C6 | 1.376 (3) |
C10—C9 | 1.523 (3) | C1—C2 | 1.389 (3) |
C10—H10A | 0.9800 | C1—C7 | 1.501 (3) |
C10—H10B | 0.9800 | C16—H16A | 0.9700 |
C14—C15 | 1.505 (3) | C16—H16B | 0.9700 |
C14—C13 | 1.518 (3) | C16—H16C | 0.9700 |
C14—H14A | 0.9800 | C7—H7A | 0.9800 |
C14—H14B | 0.9800 | C7—H7B | 0.9800 |
C11—H11A | 0.9800 | C3—C4 | 1.362 (3) |
C11—H11B | 0.9800 | C3—C2 | 1.375 (3) |
C13—H13A | 0.9800 | C3—H3A | 0.9400 |
C13—H13B | 0.9800 | C2—H2A | 0.9400 |
C8—C9 | 1.512 (3) | C5—C4 | 1.364 (4) |
C8—C7 | 1.529 (3) | C5—C6 | 1.372 (3) |
C8—H8A | 0.9800 | C5—H5A | 0.9400 |
C8—H8B | 0.9800 | C6—H6A | 0.9400 |
C9—H9A | 0.9800 | C4—H4A | 0.9400 |
C13—C12—C11 | 114.05 (17) | C8—C9—H9B | 108.8 |
C13—C12—H12A | 108.7 | C10—C9—H9B | 108.8 |
C11—C12—H12A | 108.7 | H9A—C9—H9B | 107.7 |
C13—C12—H12B | 108.7 | C14—C15—C16 | 113.7 (2) |
C11—C12—H12B | 108.7 | C14—C15—H15A | 108.8 |
H12A—C12—H12B | 107.6 | C16—C15—H15A | 108.8 |
C11—C10—C9 | 113.74 (17) | C14—C15—H15B | 108.8 |
C11—C10—H10A | 108.8 | C16—C15—H15B | 108.8 |
C9—C10—H10A | 108.8 | H15A—C15—H15B | 107.7 |
C11—C10—H10B | 108.8 | C6—C1—C2 | 117.4 (2) |
C9—C10—H10B | 108.8 | C6—C1—C7 | 120.9 (2) |
H10A—C10—H10B | 107.7 | C2—C1—C7 | 121.6 (2) |
C15—C14—C13 | 113.95 (17) | C15—C16—H16A | 109.5 |
C15—C14—H14A | 108.8 | C15—C16—H16B | 109.5 |
C13—C14—H14A | 108.8 | H16A—C16—H16B | 109.5 |
C15—C14—H14B | 108.8 | C15—C16—H16C | 109.5 |
C13—C14—H14B | 108.8 | H16A—C16—H16C | 109.5 |
H14A—C14—H14B | 107.7 | H16B—C16—H16C | 109.5 |
C10—C11—C12 | 113.93 (17) | C1—C7—C8 | 112.70 (17) |
C10—C11—H11A | 108.8 | C1—C7—H7A | 109.1 |
C12—C11—H11A | 108.8 | C8—C7—H7A | 109.1 |
C10—C11—H11B | 108.8 | C1—C7—H7B | 109.1 |
C12—C11—H11B | 108.8 | C8—C7—H7B | 109.1 |
H11A—C11—H11B | 107.7 | H7A—C7—H7B | 107.8 |
C12—C13—C14 | 113.87 (17) | C4—C3—C2 | 119.9 (2) |
C12—C13—H13A | 108.8 | C4—C3—H3A | 120.0 |
C14—C13—H13A | 108.8 | C2—C3—H3A | 120.0 |
C12—C13—H13B | 108.8 | C3—C2—C1 | 121.2 (2) |
C14—C13—H13B | 108.8 | C3—C2—H2A | 119.4 |
H13A—C13—H13B | 107.7 | C1—C2—H2A | 119.4 |
C9—C8—C7 | 113.28 (18) | C4—C5—C6 | 120.5 (2) |
C9—C8—H8A | 108.9 | C4—C5—H5A | 119.8 |
C7—C8—H8A | 108.9 | C6—C5—H5A | 119.8 |
C9—C8—H8B | 108.9 | C5—C6—C1 | 121.1 (2) |
C7—C8—H8B | 108.9 | C5—C6—H6A | 119.4 |
H8A—C8—H8B | 107.7 | C1—C6—H6A | 119.4 |
C8—C9—C10 | 113.60 (18) | C3—C4—C5 | 119.8 (2) |
C8—C9—H9A | 108.8 | C3—C4—H4A | 120.1 |
C10—C9—H9A | 108.8 | C5—C4—H4A | 120.1 |