Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801002628/om6008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801002628/om6008Isup2.hkl |
CCDC reference: 159849
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.092
- Data-to-parameter ratio = 14.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.00 From the CIF: _reflns_number_total 1808 Count of symmetry unique reflns 1807 Completeness (_total/calc) 100.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no 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.
Compound (I) was prepared as reported in the literature (Strobel et al., 1999) and recrystallized from a propan-2-ol/water mixture.
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPAK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPAK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C13H18O | Dx = 1.178 Mg m−3 |
Mr = 190.27 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 10416 reflections |
a = 7.4432 (2) Å | θ = 2.5–30.0° |
b = 10.9094 (2) Å | µ = 0.07 mm−1 |
c = 13.2137 (4) Å | T = 120 K |
V = 1072.96 (5) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.18 × 0.17 mm |
F(000) = 416 |
Nonius KappaCCD (with Oxford Cryosystems Cryostream coller) diffractometer | 1808 independent reflections |
Radiation source: fine-focus sealed tube | 1579 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans with κ offsets | θmax = 30.0°, θmin = 3.1° |
Absorption correction: multi-scan (HKL SCALEPAK; Otwinowski & Minor, 1997) | h = −10→10 |
Tmin = 0.984, Tmax = 0.988 | k = −15→15 |
10416 measured reflections | l = −18→18 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.2443P] where P = (Fo2 + 2Fc2)/3 |
1808 reflections | (Δ/σ)max = 0.001 |
127 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C13H18O | V = 1072.96 (5) Å3 |
Mr = 190.27 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.4432 (2) Å | µ = 0.07 mm−1 |
b = 10.9094 (2) Å | T = 120 K |
c = 13.2137 (4) Å | 0.23 × 0.18 × 0.17 mm |
Nonius KappaCCD (with Oxford Cryosystems Cryostream coller) diffractometer | 1808 independent reflections |
Absorption correction: multi-scan (HKL SCALEPAK; Otwinowski & Minor, 1997) | 1579 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.988 | Rint = 0.020 |
10416 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
1808 reflections | Δρmin = −0.22 e Å−3 |
127 parameters |
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 | ||
O | 0.01556 (14) | 0.82489 (9) | 0.81781 (8) | 0.0231 (2) | |
C1 | −0.12312 (19) | 0.86183 (12) | 0.74667 (10) | 0.0185 (3) | |
C2 | −0.2046 (2) | 0.74062 (13) | 0.71162 (12) | 0.0259 (3) | |
H2A | −0.2525 | 0.6954 | 0.7707 | 0.034* | |
H2B | −0.1104 | 0.6896 | 0.6797 | 0.034* | |
C3 | −0.3564 (2) | 0.76406 (14) | 0.63543 (11) | 0.0249 (3) | |
H3 | −0.4090 | 0.6842 | 0.6131 | 0.032* | |
C4 | −0.5015 (2) | 0.84188 (16) | 0.68574 (13) | 0.0325 (4) | |
H4A | −0.5527 | 0.7972 | 0.7443 | 0.042* | |
H4B | −0.5997 | 0.8582 | 0.6370 | 0.042* | |
C5 | −0.4197 (2) | 0.96290 (16) | 0.72125 (15) | 0.0377 (4) | |
H5 | −0.5152 | 1.0137 | 0.7541 | 0.049* | |
C6 | −0.3435 (3) | 1.03252 (16) | 0.63068 (17) | 0.0453 (5) | |
H6A | −0.2909 | 1.1111 | 0.6535 | 0.059* | |
H6B | −0.4408 | 1.0508 | 0.5819 | 0.059* | |
C7 | −0.1986 (3) | 0.95438 (18) | 0.57933 (13) | 0.0380 (4) | |
H7 | −0.1493 | 0.9996 | 0.5197 | 0.049* | |
C8 | −0.0466 (2) | 0.92950 (16) | 0.65548 (12) | 0.0284 (4) | |
H8A | 0.0482 | 0.8793 | 0.6232 | 0.037* | |
H8B | 0.0077 | 1.0079 | 0.6775 | 0.037* | |
C9 | −0.2794 (2) | 0.83222 (17) | 0.54396 (12) | 0.0325 (4) | |
H9A | −0.3757 | 0.8477 | 0.4939 | 0.042* | |
H9B | −0.1855 | 0.7817 | 0.5112 | 0.042* | |
C10 | −0.2688 (2) | 0.93883 (16) | 0.79773 (13) | 0.0297 (4) | |
H10A | −0.2173 | 1.0176 | 0.8212 | 0.039* | |
H10B | −0.3171 | 0.8946 | 0.8572 | 0.039* | |
C11 | 0.1189 (2) | 0.92254 (14) | 0.85968 (12) | 0.0249 (3) | |
H11A | 0.0384 | 0.9838 | 0.8914 | 0.032* | |
H11B | 0.1885 | 0.9638 | 0.8056 | 0.032* | |
C12 | 0.2411 (2) | 0.87175 (14) | 0.93563 (12) | 0.0241 (3) | |
C13 | 0.3398 (2) | 0.83105 (15) | 0.99742 (12) | 0.0291 (3) | |
H13 | 0.4190 | 0.7984 | 1.0470 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O | 0.0262 (5) | 0.0195 (5) | 0.0237 (5) | −0.0017 (4) | −0.0068 (4) | 0.0026 (4) |
C1 | 0.0197 (6) | 0.0188 (6) | 0.0171 (6) | 0.0007 (5) | −0.0009 (6) | 0.0018 (5) |
C2 | 0.0309 (8) | 0.0188 (7) | 0.0280 (7) | −0.0013 (6) | −0.0047 (7) | 0.0003 (6) |
C3 | 0.0259 (7) | 0.0232 (7) | 0.0255 (7) | −0.0027 (6) | −0.0033 (6) | −0.0025 (6) |
C4 | 0.0209 (7) | 0.0436 (9) | 0.0329 (9) | −0.0010 (7) | −0.0007 (7) | −0.0073 (7) |
C5 | 0.0277 (8) | 0.0368 (9) | 0.0487 (11) | 0.0134 (7) | −0.0100 (8) | −0.0169 (8) |
C6 | 0.0497 (11) | 0.0247 (8) | 0.0615 (13) | 0.0021 (8) | −0.0315 (11) | 0.0055 (8) |
C7 | 0.0419 (10) | 0.0456 (10) | 0.0266 (8) | −0.0171 (8) | −0.0119 (8) | 0.0162 (8) |
C8 | 0.0262 (8) | 0.0378 (8) | 0.0211 (7) | −0.0092 (7) | −0.0018 (6) | 0.0069 (6) |
C9 | 0.0309 (8) | 0.0466 (10) | 0.0201 (7) | −0.0038 (8) | −0.0038 (7) | −0.0006 (7) |
C10 | 0.0258 (7) | 0.0350 (8) | 0.0282 (8) | 0.0039 (7) | −0.0023 (7) | −0.0122 (7) |
C11 | 0.0265 (7) | 0.0219 (7) | 0.0264 (7) | −0.0009 (6) | −0.0047 (7) | 0.0011 (6) |
C12 | 0.0255 (7) | 0.0234 (7) | 0.0233 (7) | −0.0015 (6) | 0.0000 (6) | −0.0008 (6) |
C13 | 0.0303 (8) | 0.0295 (8) | 0.0276 (7) | −0.0007 (7) | −0.0047 (7) | 0.0009 (7) |
O—C11 | 1.4258 (18) | C4—C5 | 1.528 (2) |
O—C1 | 1.4531 (16) | C5—C6 | 1.527 (3) |
C1—C8 | 1.5235 (19) | C5—C10 | 1.534 (2) |
C1—C2 | 1.5268 (19) | C6—C7 | 1.533 (3) |
C1—C10 | 1.528 (2) | C7—C9 | 1.535 (3) |
C2—C3 | 1.535 (2) | C7—C8 | 1.538 (2) |
C3—C4 | 1.526 (2) | C11—C12 | 1.463 (2) |
C3—C9 | 1.530 (2) | C12—C13 | 1.185 (2) |
C11—O—C1 | 115.28 (10) | C6—C5—C4 | 109.71 (16) |
O—C1—C8 | 112.37 (11) | C6—C5—C10 | 109.23 (15) |
O—C1—C2 | 103.78 (11) | C4—C5—C10 | 110.26 (15) |
C8—C1—C2 | 109.16 (12) | C5—C6—C7 | 109.38 (14) |
O—C1—C10 | 111.76 (11) | C6—C7—C9 | 109.99 (15) |
C8—C1—C10 | 110.36 (13) | C6—C7—C8 | 109.02 (15) |
C2—C1—C10 | 109.15 (12) | C9—C7—C8 | 109.52 (15) |
C1—C2—C3 | 110.31 (12) | C1—C8—C7 | 109.15 (12) |
C4—C3—C9 | 109.80 (14) | C3—C9—C7 | 109.16 (13) |
C4—C3—C2 | 109.14 (13) | C1—C10—C5 | 108.84 (12) |
C9—C3—C2 | 108.86 (13) | O—C11—C12 | 108.58 (12) |
C3—C4—C5 | 109.42 (13) | C13—C12—C11 | 179.69 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Oi | 0.95 | 2.35 | 3.251 (2) | 158 |
Symmetry code: (i) x+1/2, −y+3/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C13H18O |
Mr | 190.27 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 120 |
a, b, c (Å) | 7.4432 (2), 10.9094 (2), 13.2137 (4) |
V (Å3) | 1072.96 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.23 × 0.18 × 0.17 |
Data collection | |
Diffractometer | Nonius KappaCCD (with Oxford Cryosystems Cryostream coller) diffractometer |
Absorption correction | Multi-scan (HKL SCALEPAK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.984, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10416, 1808, 1579 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.092, 1.02 |
No. of reflections | 1808 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.22 |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPAK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Oi | 0.95 | 2.35 | 3.251 (2) | 158.2 |
Symmetry code: (i) x+1/2, −y+3/2, −z+2. |
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1-Adamantyl propargyl ether, (I), has been found to selectively inactivate the 2B5 form of rabbit cytochrome P-450 (Strobel et al., 1999). In order to provide data for computer-modelling studies of the docking of (I) with the enzyme, the structure of (I) (Fig. 1) was determined. The compound crystallizes in the `extended' conformation as the result of weak hydrogen bonding between the acetylenic H atom (H13 attached to C13) and the O atom of a neighboring molecule. This leads to the formation of spiral chains of molecules running parallel to a (Fig. 2 and Table 1).