In the title compound, C15H14O2, the dihedral angle between the two aromatic rings is 52.75 (7)°.
Supporting information
CCDC reference: 234099
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.051
- wR factor = 0.145
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: ...We have collected data on kappa IP diffractometer and
processed using Denzo; and as we know that the DENZO image processing
package is known to have problems with certain strong reflections.
They are often excluded from the data set leading to a lower value for
the above parameter.
|
Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.90
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: ... All the authors have been approved and each author has a
genuine role for the contribution to this paper.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski and Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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.
(2-Hydroxy-5-methylphenyl)(4-methylphenyl)methanone
top
Crystal data top
C15H14O2 | Z = 2 |
Mr = 226.26 | F(000) = 240 |
Triclinic, P1 | Dx = 1.248 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4270 (5) Å | Cell parameters from 3046 reflections |
b = 7.4840 (9) Å | θ = 2.8–25.0° |
c = 10.9400 (13) Å | µ = 0.08 mm−1 |
α = 88.155 (3)° | T = 295 K |
β = 86.638 (7)° | Block, white |
γ = 82.765 (8)° | 0.25 × 0.2 × 0.2 mm |
V = 602.02 (11) Å3 | |
Data collection top
MacScience DIPLabo 32001 diffractometer | 1666 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.0°, θmin = 2.8° |
Detector resolution: 10.0 pixels mm-1 | h = −8→8 |
ω scans | k = −8→8 |
3046 measured reflections | l = −12→12 |
1905 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)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0809P)2 + 0.0862P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1905 reflections | Δρmax = 0.17 e Å−3 |
157 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.27 (3) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | |
O15 | −0.22985 (16) | 0.19497 (17) | 0.49289 (12) | 0.0681 (5) | |
O16 | −0.06188 (17) | 0.22443 (18) | 0.28141 (11) | 0.0706 (5) | |
C1 | 0.2344 (2) | 0.33782 (19) | 0.64240 (13) | 0.0517 (5) | |
C2 | 0.0782 (3) | 0.3049 (2) | 0.71379 (14) | 0.0610 (6) | |
C3 | −0.0724 (2) | 0.2563 (2) | 0.66342 (15) | 0.0620 (6) | |
C4 | −0.0750 (2) | 0.2365 (2) | 0.53842 (15) | 0.0520 (5) | |
C5 | 0.0823 (2) | 0.25895 (18) | 0.46406 (13) | 0.0464 (5) | |
C6 | 0.2325 (2) | 0.31146 (19) | 0.51877 (13) | 0.0478 (5) | |
C7 | 0.0820 (2) | 0.2334 (2) | 0.33100 (14) | 0.0507 (5) | |
C8 | 0.2541 (2) | 0.21779 (19) | 0.25287 (13) | 0.0485 (5) | |
C9 | 0.2534 (2) | 0.3055 (2) | 0.13913 (14) | 0.0584 (6) | |
C10 | 0.4075 (3) | 0.2908 (2) | 0.06170 (14) | 0.0631 (6) | |
C11 | 0.5658 (2) | 0.1847 (2) | 0.09308 (14) | 0.0562 (5) | |
C12 | 0.5639 (2) | 0.0938 (2) | 0.20591 (14) | 0.0538 (5) | |
C13 | 0.4119 (2) | 0.11068 (19) | 0.28521 (13) | 0.0499 (5) | |
C14 | 0.3953 (3) | 0.3991 (3) | 0.69801 (15) | 0.0667 (6) | |
C17 | 0.7336 (3) | 0.1691 (3) | 0.00878 (18) | 0.0787 (8) | |
H2 | 0.07690 | 0.31640 | 0.79820 | 0.0730* | |
H3 | −0.17370 | 0.23640 | 0.71370 | 0.0740* | |
H6 | 0.33530 | 0.32920 | 0.46940 | 0.0570* | |
H9 | 0.14810 | 0.37480 | 0.11490 | 0.0700* | |
H10 | 0.40520 | 0.35330 | −0.01320 | 0.0760* | |
H12 | 0.66760 | 0.01990 | 0.22840 | 0.0650* | |
H13 | 0.41480 | 0.05010 | 0.36080 | 0.0600* | |
H14A | 0.48650 | 0.41780 | 0.63460 | 0.1000* | |
H14B | 0.44430 | 0.30880 | 0.75550 | 0.1000* | |
H14C | 0.35810 | 0.50980 | 0.73950 | 0.1000* | |
H15 | −0.21560 | 0.18660 | 0.41830 | 0.1020* | |
H17A | 0.73500 | 0.06710 | −0.04240 | 0.1180* | |
H17B | 0.83940 | 0.15380 | 0.05630 | 0.1180* | |
H17C | 0.73390 | 0.27660 | −0.04150 | 0.1180* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O15 | 0.0509 (8) | 0.0782 (8) | 0.0764 (8) | −0.0171 (6) | 0.0072 (6) | −0.0036 (6) |
O16 | 0.0545 (9) | 0.0955 (10) | 0.0650 (8) | −0.0172 (6) | −0.0056 (6) | −0.0162 (6) |
C1 | 0.0593 (11) | 0.0474 (8) | 0.0465 (8) | −0.0004 (6) | −0.0008 (6) | −0.0003 (6) |
C2 | 0.0713 (12) | 0.0647 (10) | 0.0423 (8) | 0.0038 (8) | 0.0068 (7) | 0.0029 (7) |
C3 | 0.0595 (12) | 0.0653 (10) | 0.0573 (10) | −0.0034 (8) | 0.0163 (8) | 0.0073 (7) |
C4 | 0.0507 (10) | 0.0446 (8) | 0.0589 (9) | −0.0035 (6) | 0.0060 (7) | 0.0023 (6) |
C5 | 0.0495 (9) | 0.0410 (7) | 0.0480 (8) | −0.0058 (6) | 0.0041 (6) | −0.0014 (6) |
C6 | 0.0523 (10) | 0.0445 (8) | 0.0459 (8) | −0.0071 (6) | 0.0052 (6) | −0.0011 (6) |
C7 | 0.0523 (10) | 0.0485 (8) | 0.0523 (9) | −0.0100 (6) | −0.0010 (7) | −0.0064 (6) |
C8 | 0.0569 (10) | 0.0476 (8) | 0.0426 (8) | −0.0119 (6) | −0.0008 (6) | −0.0076 (6) |
C9 | 0.0651 (11) | 0.0638 (10) | 0.0460 (8) | −0.0057 (8) | −0.0046 (7) | −0.0018 (7) |
C10 | 0.0787 (13) | 0.0720 (11) | 0.0402 (8) | −0.0177 (9) | −0.0005 (7) | −0.0001 (7) |
C11 | 0.0651 (11) | 0.0604 (9) | 0.0463 (8) | −0.0217 (8) | 0.0079 (7) | −0.0144 (7) |
C12 | 0.0533 (10) | 0.0523 (9) | 0.0564 (9) | −0.0084 (7) | 0.0014 (7) | −0.0101 (7) |
C13 | 0.0572 (10) | 0.0479 (8) | 0.0452 (8) | −0.0101 (6) | 0.0001 (6) | −0.0015 (6) |
C14 | 0.0765 (13) | 0.0728 (11) | 0.0518 (9) | −0.0088 (9) | −0.0091 (8) | −0.0077 (8) |
C17 | 0.0775 (14) | 0.0981 (14) | 0.0627 (11) | −0.0260 (11) | 0.0207 (9) | −0.0195 (10) |
Geometric parameters (Å, º) top
O15—C4 | 1.354 (2) | C11—C17 | 1.501 (3) |
O16—C7 | 1.237 (2) | C11—C12 | 1.390 (2) |
O15—H15 | 0.8201 | C12—C13 | 1.378 (2) |
C1—C2 | 1.404 (3) | C2—H2 | 0.9296 |
C1—C14 | 1.500 (3) | C3—H3 | 0.9302 |
C1—C6 | 1.374 (2) | C6—H6 | 0.9300 |
C2—C3 | 1.369 (3) | C9—H9 | 0.9296 |
C3—C4 | 1.382 (2) | C10—H10 | 0.9303 |
C4—C5 | 1.409 (2) | C12—H12 | 0.9305 |
C5—C7 | 1.474 (2) | C13—H13 | 0.9302 |
C5—C6 | 1.400 (2) | C14—H14A | 0.9603 |
C7—C8 | 1.490 (2) | C14—H14B | 0.9603 |
C8—C13 | 1.391 (2) | C14—H14C | 0.9595 |
C8—C9 | 1.388 (2) | C17—H17A | 0.9598 |
C9—C10 | 1.378 (3) | C17—H17B | 0.9603 |
C10—C11 | 1.388 (2) | C17—H17C | 0.9600 |
| | | |
O15···O16 | 2.5798 (18) | H6···C8 | 2.6630 |
O16···C12i | 3.220 (2) | H6···C13 | 2.6272 |
O16···O15 | 2.5798 (18) | H6···H13 | 2.4269 |
O15···H13ii | 2.8285 | H6···H14A | 2.3388 |
O15···H14Ai | 2.9191 | H9···O16 | 2.6446 |
O16···H9 | 2.6446 | H10···H14Bvii | 2.5577 |
O16···H12i | 2.7721 | H10···H17C | 2.4403 |
O16···H15 | 1.8654 | H12···O16iv | 2.7721 |
O16···H17Bi | 2.6972 | H12···H17B | 2.4690 |
O16···H14Ciii | 2.7886 | H12···C1v | 3.0135 |
C2···C7iii | 3.538 (2) | H12···C2v | 2.9594 |
C4···C6iii | 3.487 (2) | H13···C5 | 2.9380 |
C6···C13 | 3.147 (2) | H13···C6 | 2.8146 |
C6···C4iii | 3.487 (2) | H13···H6 | 2.4269 |
C7···C2iii | 3.538 (2) | H13···O15ii | 2.8285 |
C12···O16iv | 3.220 (2) | H14A···O15iv | 2.9191 |
C13···C6 | 3.147 (2) | H14A···H6 | 2.3388 |
C1···H12v | 3.0135 | H14B···H10viii | 2.5577 |
C2···H12v | 2.9594 | H14B···C12v | 3.0367 |
C5···H13 | 2.9380 | H14C···O16iii | 2.7886 |
C6···H13 | 2.8146 | H15···O16 | 1.8654 |
C7···H15 | 2.4179 | H15···C7 | 2.4179 |
C8···H6 | 2.6630 | H15···C12i | 3.0659 |
C9···H17Avi | 3.0037 | H17A···C9vi | 3.0037 |
C10···H17Avi | 3.0192 | H17A···C10vi | 3.0192 |
C12···H15iv | 3.0659 | H17B···O16iv | 2.6972 |
C12···H14Bv | 3.0367 | H17B···H12 | 2.4690 |
C13···H6 | 2.6272 | H17C···H10 | 2.4403 |
| | | |
C4—O15—H15 | 109.47 | C1—C2—H2 | 118.90 |
C2—C1—C14 | 121.76 (14) | C3—C2—H2 | 118.83 |
C6—C1—C14 | 121.59 (14) | C2—C3—H3 | 119.78 |
C2—C1—C6 | 116.64 (14) | C4—C3—H3 | 119.74 |
C1—C2—C3 | 122.28 (14) | C1—C6—H6 | 118.61 |
C2—C3—C4 | 120.49 (15) | C5—C6—H6 | 118.64 |
O15—C4—C3 | 118.06 (14) | C8—C9—H9 | 119.74 |
O15—C4—C5 | 122.84 (14) | C10—C9—H9 | 119.66 |
C3—C4—C5 | 119.10 (14) | C9—C10—H10 | 119.26 |
C4—C5—C6 | 118.61 (13) | C11—C10—H10 | 119.34 |
C4—C5—C7 | 119.38 (13) | C11—C12—H12 | 119.26 |
C6—C5—C7 | 121.97 (13) | C13—C12—H12 | 119.25 |
C1—C6—C5 | 122.75 (14) | C8—C13—H13 | 119.79 |
O16—C7—C8 | 118.28 (14) | C12—C13—H13 | 119.83 |
C5—C7—C8 | 121.11 (13) | C1—C14—H14A | 109.46 |
O16—C7—C5 | 120.61 (14) | C1—C14—H14B | 109.47 |
C7—C8—C13 | 123.10 (13) | C1—C14—H14C | 109.46 |
C9—C8—C13 | 118.50 (13) | H14A—C14—H14B | 109.48 |
C7—C8—C9 | 118.28 (13) | H14A—C14—H14C | 109.49 |
C8—C9—C10 | 120.60 (14) | H14B—C14—H14C | 109.47 |
C9—C10—C11 | 121.40 (14) | C11—C17—H17A | 109.54 |
C10—C11—C12 | 117.60 (14) | C11—C17—H17B | 109.48 |
C10—C11—C17 | 121.34 (15) | C11—C17—H17C | 109.47 |
C12—C11—C17 | 121.06 (15) | H17A—C17—H17B | 109.48 |
C11—C12—C13 | 121.49 (14) | H17A—C17—H17C | 109.44 |
C8—C13—C12 | 120.38 (13) | H17B—C17—H17C | 109.42 |
| | | |
C2—C1—C6—C5 | 1.6 (2) | C6—C5—C7—O16 | −164.75 (15) |
C14—C1—C6—C5 | −178.26 (15) | C5—C7—C8—C9 | −138.87 (14) |
C6—C1—C2—C3 | −2.7 (2) | C5—C7—C8—C13 | 45.2 (2) |
C14—C1—C2—C3 | 177.18 (16) | O16—C7—C8—C13 | −134.77 (16) |
C1—C2—C3—C4 | 0.5 (2) | O16—C7—C8—C9 | 41.1 (2) |
C2—C3—C4—O15 | −177.52 (14) | C7—C8—C13—C12 | 176.32 (14) |
C2—C3—C4—C5 | 2.9 (2) | C7—C8—C9—C10 | −177.97 (14) |
O15—C4—C5—C6 | 176.57 (14) | C13—C8—C9—C10 | −1.9 (2) |
C3—C4—C5—C7 | 178.43 (13) | C9—C8—C13—C12 | 0.5 (2) |
O15—C4—C5—C7 | −1.2 (2) | C8—C9—C10—C11 | 1.8 (2) |
C3—C4—C5—C6 | −3.8 (2) | C9—C10—C11—C17 | −179.88 (16) |
C4—C5—C6—C1 | 1.6 (2) | C9—C10—C11—C12 | −0.2 (2) |
C4—C5—C7—C8 | −167.12 (13) | C10—C11—C12—C13 | −1.3 (2) |
C7—C5—C6—C1 | 179.26 (14) | C17—C11—C12—C13 | 178.42 (16) |
C4—C5—C7—O16 | 12.9 (2) | C11—C12—C13—C8 | 1.1 (2) |
C6—C5—C7—C8 | 15.2 (2) | | |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x+1, y, z; (v) −x+1, −y, −z+1; (vi) −x+1, −y, −z; (vii) x, y, z−1; (viii) x, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O16 | 0.82 | 1.87 | 2.5798 (18) | 145 |