(4-Chloro­phen­yl)(2-hydr­oxy-5-methyl­phen­yl)methanone

In the title compound, C₁₄H₁₁ClO₂, the dihedral angle between the two aromatic rings is 51.98 (11)°. The mol­ecular conformation is stabilized by a strong intra­molecular O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.153
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.90

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
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.03
           From the CIF: _diffrn_reflns_theta_full          25.03
           From the CIF: _reflns_number_total               1898
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2104
           Completeness (_total/calc)             90.21%
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
   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & 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.

(4-Chlorophenyl)(2-hydroxy-5-methylphenyl)methanone

Crystal data

C14H11ClO2	Z = 2
Mr = 246.68	F(000) = 256
Triclinic, P1	Dx = 1.375 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.362 (8) Å	Cell parameters from 3083 reflections
b = 7.44 (1) Å	θ = 2.8–25.0°
c = 11.001 (14) Å	µ = 0.31 mm^−1
α = 88.144 (5)°	T = 295 K
β = 85.622 (9)°	Block, pale yellow
γ = 82.831 (8)°	0.25 × 0.20 × 0.20 mm
V = 596.0 (13) Å^3

Data collection

MacScience DIPLabo 32001 diffractometer	1610 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
Detector resolution: 10.0 pixels mm^-1	h = −8→8
ω scans	k = −8→8
3083 measured reflections	l = −13→13
1898 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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0905P)^2 + 0.1264P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
1898 reflections	Δρmax = 0.24 e Å^−3
156 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.14 (2)

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
Cl17	0.24078 (11)	0.33354 (12)	0.50699 (6)	0.0938 (4)
O15	1.2327 (2)	0.3053 (2)	0.00083 (16)	0.0692 (6)
O16	1.0605 (2)	0.2804 (3)	0.21162 (16)	0.0738 (7)
C1	0.7673 (3)	0.1617 (3)	−0.14520 (19)	0.0529 (7)
C2	0.9251 (3)	0.1934 (3)	−0.2173 (2)	0.0611 (8)
C3	1.0764 (3)	0.2424 (3)	−0.1684 (2)	0.0623 (8)
C4	1.0773 (3)	0.2633 (3)	−0.0437 (2)	0.0538 (7)
C5	0.9174 (3)	0.2421 (3)	0.03186 (18)	0.0481 (6)
C6	0.7666 (3)	0.1887 (3)	−0.02159 (18)	0.0485 (7)
C7	0.9168 (3)	0.2693 (3)	0.1637 (2)	0.0537 (7)
C8	0.7424 (3)	0.2842 (3)	0.24424 (18)	0.0511 (7)
C9	0.7468 (4)	0.1969 (4)	0.3579 (2)	0.0646 (8)
C10	0.5925 (4)	0.2098 (4)	0.4381 (2)	0.0700 (9)
C11	0.4350 (3)	0.3152 (3)	0.4061 (2)	0.0605 (8)
C12	0.4283 (3)	0.4065 (3)	0.2950 (2)	0.0563 (7)
C13	0.5826 (3)	0.3885 (3)	0.21368 (18)	0.0527 (7)
C14	0.6060 (3)	0.0993 (4)	−0.1999 (2)	0.0670 (8)
H2	0.92740	0.18080	−0.30130	0.0730*
H3	1.17940	0.26180	−0.21910	0.0750*
H6	0.66200	0.17080	0.02800	0.0580*
H9	0.85470	0.12920	0.38010	0.0780*
H10	0.59470	0.14810	0.51300	0.0840*
H12	0.32200	0.47890	0.27490	0.0680*
H13	0.57860	0.44720	0.13780	0.0630*
H14A	0.64090	−0.01890	−0.23290	0.1010*
H14B	0.56640	0.18280	−0.26370	0.1010*
H14C	0.50740	0.09410	−0.13800	0.1010*
H15	1.21710	0.31390	0.07510	0.1040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl17	0.0839 (6)	0.1296 (8)	0.0675 (5)	−0.0298 (5)	0.0297 (4)	−0.0156 (4)
O15	0.0476 (9)	0.0809 (12)	0.0802 (12)	−0.0177 (8)	0.0053 (8)	−0.0036 (9)
O16	0.0541 (10)	0.1016 (14)	0.0687 (11)	−0.0167 (9)	−0.0072 (8)	−0.0154 (9)
C1	0.0559 (12)	0.0529 (12)	0.0486 (11)	−0.0038 (9)	−0.0005 (9)	0.0017 (9)
C2	0.0672 (14)	0.0654 (15)	0.0462 (11)	0.0010 (11)	0.0071 (10)	0.0035 (9)
C3	0.0530 (13)	0.0688 (15)	0.0612 (14)	−0.0054 (11)	0.0139 (10)	0.0080 (10)
C4	0.0455 (11)	0.0483 (12)	0.0659 (13)	−0.0057 (9)	0.0041 (9)	0.0032 (9)
C5	0.0476 (11)	0.0445 (11)	0.0514 (11)	−0.0069 (8)	0.0029 (8)	0.0002 (8)
C6	0.0477 (11)	0.0473 (12)	0.0495 (11)	−0.0068 (9)	0.0044 (8)	0.0014 (8)
C7	0.0484 (11)	0.0556 (13)	0.0586 (13)	−0.0119 (9)	−0.0013 (9)	−0.0070 (9)
C8	0.0528 (12)	0.0553 (13)	0.0466 (11)	−0.0127 (9)	−0.0003 (8)	−0.0076 (8)
C9	0.0690 (15)	0.0748 (16)	0.0494 (12)	−0.0051 (12)	−0.0061 (10)	−0.0014 (10)
C10	0.0853 (18)	0.0831 (18)	0.0423 (11)	−0.0171 (14)	0.0003 (11)	0.0026 (11)
C11	0.0638 (13)	0.0701 (15)	0.0496 (12)	−0.0212 (11)	0.0095 (10)	−0.0130 (10)
C12	0.0525 (12)	0.0608 (13)	0.0567 (12)	−0.0126 (10)	0.0012 (9)	−0.0089 (10)
C13	0.0548 (12)	0.0580 (13)	0.0463 (11)	−0.0135 (10)	0.0002 (9)	−0.0007 (9)
C14	0.0699 (15)	0.0780 (16)	0.0542 (13)	−0.0104 (12)	−0.0067 (11)	−0.0063 (11)

Geometric parameters (Å, º)

Cl17—C11	1.736 (3)	C9—C10	1.380 (4)
O15—C4	1.353 (3)	C10—C11	1.379 (4)
O16—C7	1.230 (3)	C11—C12	1.380 (4)
O15—H15	0.8198	C12—C13	1.387 (4)
C1—C6	1.381 (3)	C2—H2	0.9305
C1—C14	1.501 (4)	C3—H3	0.9298
C1—C2	1.396 (4)	C6—H6	0.9301
C2—C3	1.367 (4)	C9—H9	0.9307
C3—C4	1.386 (4)	C10—H10	0.9304
C4—C5	1.411 (4)	C12—H12	0.9300
C5—C6	1.400 (4)	C13—H13	0.9302
C5—C7	1.470 (4)	C14—H14A	0.9598
C7—C8	1.498 (4)	C14—H14B	0.9599
C8—C13	1.384 (4)	C14—H14C	0.9602
C8—C9	1.391 (4)
Cl17···H3^i	3.0524	C12···H14B^vi	3.0686
O15···O16	2.569 (4)	C13···H6	2.6331
O16···C12^ii	3.182 (5)	H3···Cl17^viii	3.0524
O16···O15	2.569 (4)	H6···C8	2.6816
O15···H13^iii	2.7892	H6···C13	2.6331
O15···H14C^ii	2.7897	H6···H13	2.4078
O16···H9	2.6188	H6···H14C	2.3458
O16···H12^ii	2.7116	H9···O16	2.6188
O16···H15	1.8520	H10···H14B^ix	2.4686
O16···H14A^iv	2.7666	H12···O16^v	2.7116
C2···C7^iv	3.539 (6)	H12···C1^vi	3.0125
C4···C6^iv	3.486 (6)	H12···C2^vi	2.9367
C6···C13	3.155 (5)	H13···C5	2.9376
C6···C4^iv	3.486 (6)	H13···C6	2.8058
C7···C2^iv	3.539 (6)	H13···H6	2.4078
C12···O16^v	3.182 (5)	H13···O15^iii	2.7892
C13···C6	3.155 (5)	H14A···O16^iv	2.7666
C1···H12^vi	3.0125	H14A···C11^vii	3.0894
C2···H12^vi	2.9367	H14A···C12^vii	3.0967
C5···H13	2.9376	H14B···H10^x	2.4686
C6···H13	2.8058	H14B···C12^vi	3.0686
C7···H15	2.4044	H14C···O15^v	2.7897
C8···H6	2.6816	H14C···H6	2.3458
C11···H14A^vii	3.0894	H15···O16	1.8520
C12···H14A^vii	3.0967	H15···C7	2.4044
C4—O15—H15	109.47	C10—C11—C12	121.3 (2)
C2—C1—C14	121.28 (19)	C11—C12—C13	119.0 (2)
C6—C1—C14	121.5 (2)	C8—C13—C12	120.70 (19)
C2—C1—C6	117.2 (2)	C1—C2—H2	118.99
C1—C2—C3	122.1 (2)	C3—C2—H2	118.92
C2—C3—C4	120.4 (2)	C2—C3—H3	119.79
O15—C4—C3	118.2 (2)	C4—C3—H3	119.78
O15—C4—C5	122.40 (19)	C1—C6—H6	118.74
C3—C4—C5	119.4 (2)	C5—C6—H6	118.80
C4—C5—C6	118.27 (19)	C8—C9—H9	119.77
C4—C5—C7	119.3 (2)	C10—C9—H9	119.67
C6—C5—C7	122.33 (19)	C9—C10—H10	120.37
C1—C6—C5	122.5 (2)	C11—C10—H10	120.34
O16—C7—C8	117.7 (2)	C11—C12—H12	120.57
C5—C7—C8	121.46 (19)	C13—C12—H12	120.48
O16—C7—C5	120.8 (2)	C8—C13—H13	119.67
C7—C8—C13	123.12 (19)	C12—C13—H13	119.63
C9—C8—C13	119.2 (2)	C1—C14—H14A	109.50
C7—C8—C9	117.6 (2)	C1—C14—H14B	109.48
C8—C9—C10	120.6 (3)	C1—C14—H14C	109.46
C9—C10—C11	119.3 (2)	H14A—C14—H14B	109.50
Cl17—C11—C10	119.58 (18)	H14A—C14—H14C	109.44
Cl17—C11—C12	119.15 (17)	H14B—C14—H14C	109.45
C2—C1—C6—C5	−1.3 (3)	C6—C5—C7—O16	165.4 (2)
C14—C1—C6—C5	178.2 (2)	C5—C7—C8—C9	139.1 (2)
C6—C1—C2—C3	2.5 (3)	C5—C7—C8—C13	−44.8 (3)
C14—C1—C2—C3	−177.0 (2)	O16—C7—C8—C13	135.3 (2)
C1—C2—C3—C4	−0.3 (3)	O16—C7—C8—C9	−40.8 (3)
C2—C3—C4—O15	177.6 (2)	C7—C8—C13—C12	−175.9 (2)
C2—C3—C4—C5	−3.0 (3)	C7—C8—C9—C10	178.0 (2)
O15—C4—C5—C6	−176.5 (2)	C13—C8—C9—C10	1.8 (4)
C3—C4—C5—C7	−178.3 (2)	C9—C8—C13—C12	0.1 (3)
O15—C4—C5—C7	1.1 (3)	C8—C9—C10—C11	−2.1 (4)
C3—C4—C5—C6	4.1 (3)	C9—C10—C11—C12	0.6 (4)
C4—C5—C6—C1	−2.0 (3)	C9—C10—C11—Cl17	−179.5 (2)
C4—C5—C7—C8	168.0 (2)	Cl17—C11—C12—C13	−178.70 (17)
C7—C5—C6—C1	−179.5 (2)	C10—C11—C12—C13	1.2 (3)
C4—C5—C7—O16	−12.1 (3)	C11—C12—C13—C8	−1.5 (3)
C6—C5—C7—C8	−14.6 (3)

Symmetry codes: (i) x−1, y, z+1; (ii) x+1, y, z; (iii) −x+2, −y+1, −z; (iv) −x+2, −y, −z; (v) x−1, y, z; (vi) −x+1, −y+1, −z; (vii) −x+1, −y, −z; (viii) x+1, y, z−1; (ix) x, y, z+1; (x) 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	1.85	2.569 (4)	145