In the title compound, C15H14O2, the dihedral angle between the two benzene rings is 56.34 (7)°.
Supporting information
CCDC reference: 283778
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.002 Å
- R factor = 0.048
- wR factor = 0.143
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
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Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski and Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
C15H14O2 | F(000) = 480 |
Mr = 226.26 | Dx = 1.239 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4020 reflections |
a = 7.592 (4) Å | θ = 2.3–25.0° |
b = 14.147 (7) Å | µ = 0.08 mm−1 |
c = 11.342 (7) Å | T = 295 K |
β = 95.231 (2)° | Block, colourless |
V = 1213.1 (12) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 | |
Data collection top
MacScience DIPLabo 32001 diffractometer | 1882 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
Detector resolution: 10.0 pixels mm-1 | h = −9→9 |
ω scans | k = −16→16 |
4020 measured reflections | l = −13→13 |
2123 independent reflections | |
Refinement top
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 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0795P)2 + 0.1331P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.001 |
2123 reflections | Δρmax = 0.41 e Å−3 |
157 parameters | Δρmin = −0.37 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: 0.22 (2) |
Special details top
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 on F^2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F^2, conventional
R-factors R are based on F, with F set to zero for
negative F^2. The observed criterion of F^2 > σ(F^2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F^2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O17 | 0.36706 (15) | 0.10452 (7) | 0.94637 (10) | 0.0587 (4) | |
C4 | 0.26855 (18) | 0.39251 (10) | 0.96424 (12) | 0.0453 (4) | |
C1 | 0.33803 (18) | 0.19934 (10) | 0.94589 (12) | 0.0458 (4) | |
C8 | 0.24024 (19) | 0.49513 (10) | 0.98311 (13) | 0.0490 (4) | |
C9 | 0.20172 (18) | 0.56091 (10) | 0.88073 (13) | 0.0461 (4) | |
C2 | 0.25393 (19) | 0.23400 (10) | 1.04091 (13) | 0.0501 (4) | |
H2 | 0.2182 | 0.1914 | 1.1001 | 0.060* | |
C6 | 0.38615 (19) | 0.26117 (11) | 0.85936 (12) | 0.0499 (4) | |
H6 | 0.4441 | 0.2373 | 0.7937 | 0.060* | |
C5 | 0.34971 (19) | 0.35656 (10) | 0.86891 (12) | 0.0479 (4) | |
H5 | 0.3817 | 0.3982 | 0.8076 | 0.058* | |
C10 | 0.24350 (18) | 0.65607 (10) | 0.89759 (13) | 0.0500 (4) | |
H10 | 0.3070 | 0.6763 | 0.9703 | 0.060* | |
C3 | 0.22151 (19) | 0.32911 (11) | 1.05064 (12) | 0.0490 (4) | |
H3 | 0.1658 | 0.3520 | 1.1178 | 0.059* | |
O16 | 0.24448 (19) | 0.52616 (8) | 1.08362 (10) | 0.0749 (4) | |
C14 | 0.11188 (19) | 0.53244 (11) | 0.77437 (14) | 0.0539 (4) | |
H14 | 0.0845 | 0.4668 | 0.7616 | 0.065* | |
C11 | 0.19742 (19) | 0.72333 (11) | 0.81108 (14) | 0.0542 (4) | |
C12 | 0.1069 (2) | 0.69302 (13) | 0.70616 (15) | 0.0632 (5) | |
H12 | 0.0722 | 0.7374 | 0.6444 | 0.076* | |
C13 | 0.0641 (2) | 0.59906 (13) | 0.68804 (14) | 0.0626 (5) | |
H13 | 0.0006 | 0.5802 | 0.6147 | 0.075* | |
C7 | 0.4530 (3) | 0.06452 (12) | 0.85195 (17) | 0.0709 (5) | |
H7A | 0.4758 | −0.0012 | 0.8677 | 0.106* | |
H7B | 0.5627 | 0.0968 | 0.8450 | 0.106* | |
H7C | 0.3784 | 0.0709 | 0.7794 | 0.106* | |
C15 | 0.2407 (3) | 0.82610 (12) | 0.83278 (19) | 0.0736 (5) | |
H15A | 0.2383 | 0.8587 | 0.7584 | 0.110* | |
H15B | 0.3565 | 0.8315 | 0.8740 | 0.110* | |
H15C | 0.1551 | 0.8536 | 0.8798 | 0.110* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O17 | 0.0704 (7) | 0.0439 (6) | 0.0613 (7) | 0.0045 (5) | 0.0041 (5) | 0.0042 (5) |
C4 | 0.0450 (7) | 0.0472 (8) | 0.0428 (7) | −0.0025 (5) | −0.0002 (6) | 0.0033 (6) |
C1 | 0.0447 (7) | 0.0447 (8) | 0.0464 (8) | −0.0014 (5) | −0.0043 (6) | 0.0024 (6) |
C8 | 0.0535 (8) | 0.0475 (8) | 0.0460 (8) | −0.0041 (6) | 0.0040 (6) | −0.0010 (6) |
C9 | 0.0421 (7) | 0.0470 (8) | 0.0491 (8) | 0.0007 (6) | 0.0039 (6) | 0.0028 (6) |
C2 | 0.0560 (8) | 0.0495 (8) | 0.0448 (8) | −0.0045 (6) | 0.0032 (6) | 0.0095 (6) |
C6 | 0.0522 (8) | 0.0528 (8) | 0.0453 (8) | 0.0021 (6) | 0.0070 (6) | 0.0007 (6) |
C5 | 0.0523 (8) | 0.0481 (8) | 0.0437 (8) | −0.0021 (6) | 0.0068 (6) | 0.0063 (6) |
C10 | 0.0467 (8) | 0.0492 (8) | 0.0535 (8) | −0.0004 (6) | 0.0008 (6) | 0.0027 (6) |
C3 | 0.0527 (8) | 0.0537 (8) | 0.0411 (7) | −0.0014 (6) | 0.0065 (6) | 0.0018 (6) |
O16 | 0.1252 (12) | 0.0527 (7) | 0.0467 (7) | −0.0029 (6) | 0.0080 (6) | −0.0034 (5) |
C14 | 0.0484 (8) | 0.0565 (9) | 0.0558 (9) | −0.0020 (6) | −0.0005 (6) | −0.0018 (7) |
C11 | 0.0457 (8) | 0.0522 (9) | 0.0647 (10) | 0.0032 (6) | 0.0052 (7) | 0.0111 (7) |
C12 | 0.0542 (9) | 0.0709 (11) | 0.0633 (10) | 0.0075 (7) | −0.0013 (7) | 0.0192 (8) |
C13 | 0.0548 (9) | 0.0765 (11) | 0.0540 (9) | 0.0024 (8) | −0.0096 (7) | 0.0032 (8) |
C7 | 0.0875 (12) | 0.0510 (9) | 0.0746 (11) | 0.0102 (8) | 0.0098 (9) | −0.0055 (8) |
C15 | 0.0782 (12) | 0.0522 (10) | 0.0897 (13) | 0.0021 (8) | 0.0039 (10) | 0.0160 (9) |
Geometric parameters (Å, º) top
O17—C1 | 1.3593 (17) | C10—C11 | 1.389 (2) |
O17—C7 | 1.421 (2) | C10—H10 | 0.96 |
C4—C5 | 1.389 (2) | C3—H3 | 0.96 |
C4—C3 | 1.399 (2) | C14—C13 | 1.383 (2) |
C4—C8 | 1.486 (2) | C14—H14 | 0.96 |
C1—C6 | 1.388 (2) | C11—C12 | 1.387 (2) |
C1—C2 | 1.391 (2) | C11—C15 | 1.506 (2) |
C8—O16 | 1.2192 (18) | C12—C13 | 1.379 (3) |
C8—C9 | 1.496 (2) | C12—H12 | 0.96 |
C9—C14 | 1.390 (2) | C13—H13 | 0.96 |
C9—C10 | 1.392 (2) | C7—H7A | 0.96 |
C2—C3 | 1.374 (2) | C7—H7B | 0.96 |
C2—H2 | 0.96 | C7—H7C | 0.96 |
C6—C5 | 1.384 (2) | C15—H15A | 0.96 |
C6—H6 | 0.96 | C15—H15B | 0.96 |
C5—H5 | 0.96 | C15—H15C | 0.96 |
| | | |
C1—O17—C7 | 118.38 (12) | C2—C3—H3 | 119.3 |
C5—C4—C3 | 118.06 (13) | C4—C3—H3 | 119.9 |
C5—C4—C8 | 123.38 (12) | C13—C14—C9 | 119.55 (15) |
C3—C4—C8 | 118.43 (13) | C13—C14—H14 | 120.9 |
O17—C1—C6 | 124.86 (13) | C9—C14—H14 | 119.6 |
O17—C1—C2 | 115.50 (12) | C12—C11—C10 | 117.88 (15) |
C6—C1—C2 | 119.64 (13) | C12—C11—C15 | 121.51 (14) |
O16—C8—C4 | 119.64 (13) | C10—C11—C15 | 120.59 (15) |
O16—C8—C9 | 119.24 (13) | C13—C12—C11 | 121.16 (15) |
C4—C8—C9 | 121.10 (12) | C13—C12—H12 | 118.5 |
C14—C9—C10 | 119.14 (13) | C11—C12—H12 | 120.4 |
C14—C9—C8 | 122.62 (13) | C12—C13—C14 | 120.53 (15) |
C10—C9—C8 | 117.96 (13) | C12—C13—H13 | 119.3 |
C3—C2—C1 | 120.37 (13) | C14—C13—H13 | 120.2 |
C3—C2—H2 | 119.7 | O17—C7—H7A | 109.5 |
C1—C2—H2 | 120.0 | O17—C7—H7B | 109.5 |
C5—C6—C1 | 119.45 (13) | H7A—C7—H7B | 109.5 |
C5—C6—H6 | 120.8 | O17—C7—H7C | 109.5 |
C1—C6—H6 | 119.7 | H7A—C7—H7C | 109.5 |
C6—C5—C4 | 121.61 (13) | H7B—C7—H7C | 109.5 |
C6—C5—H5 | 118.5 | C11—C15—H15A | 109.5 |
C4—C5—H5 | 119.9 | C11—C15—H15B | 109.5 |
C11—C10—C9 | 121.74 (14) | H15A—C15—H15B | 109.5 |
C11—C10—H10 | 118.5 | C11—C15—H15C | 109.5 |
C9—C10—H10 | 119.8 | H15A—C15—H15C | 109.5 |
C2—C3—C4 | 120.84 (14) | H15B—C15—H15C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O16i | 0.96 | 2.57 | 3.517 (3) | 169 |
Symmetry code: (i) x, −y+3/2, z−1/2. |