(2-Hydr­oxy-5-methyl­phen­yl)(4-methyl­phen­yl)methanone

In the title compound, C₁₅H₁₄O₂, the dihedral angle between the two aromatic rings is 52.75 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0809P)^2 + 0.0862P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···C12^i	3.220 (2)	H6···C13	2.6272
O16···O15	2.5798 (18)	H6···H13	2.4269
O15···H13^ii	2.8285	H6···H14A	2.3388
O15···H14A^i	2.9191	H9···O16	2.6446
O16···H9	2.6446	H10···H14B^vii	2.5577
O16···H12^i	2.7721	H10···H17C	2.4403
O16···H15	1.8654	H12···O16^iv	2.7721
O16···H17B^i	2.6972	H12···H17B	2.4690
O16···H14C^iii	2.7886	H12···C1^v	3.0135
C2···C7^iii	3.538 (2)	H12···C2^v	2.9594
C4···C6^iii	3.487 (2)	H13···C5	2.9380
C6···C13	3.147 (2)	H13···C6	2.8146
C6···C4^iii	3.487 (2)	H13···H6	2.4269
C7···C2^iii	3.538 (2)	H13···O15^ii	2.8285
C12···O16^iv	3.220 (2)	H14A···O15^iv	2.9191
C13···C6	3.147 (2)	H14A···H6	2.3388
C1···H12^v	3.0135	H14B···H10^viii	2.5577
C2···H12^v	2.9594	H14B···C12^v	3.0367
C5···H13	2.9380	H14C···O16^iii	2.7886
C6···H13	2.8146	H15···O16	1.8654
C7···H15	2.4179	H15···C7	2.4179
C8···H6	2.6630	H15···C12^i	3.0659
C9···H17A^vi	3.0037	H17A···C9^vi	3.0037
C10···H17A^vi	3.0192	H17A···C10^vi	3.0192
C12···H15^iv	3.0659	H17B···O16^iv	2.6972
C12···H14B^v	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)

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···O16	0.82	1.87	2.5798 (18)	145