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In the title compound, C15H14ClO2, the dihedral angle between the two benzene rings is 57.37 (12)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031776/sj6131sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031776/sj6131Isup2.hkl
Contains datablock I

CCDC reference: 219251

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.151
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
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 25.01 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 1945 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2108 Completeness (_total/calc) 92.27% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
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

Computing details top

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.

(3-Chlorophenyl)(2-hydroxy-5-methylphenyl)methanone top
Crystal data top
C14H11ClO2F(000) = 512
Mr = 246.68Dx = 1.375 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3643 reflections
a = 10.4850 (9) Åθ = 2.3–25.0°
b = 7.8230 (4) ŵ = 0.31 mm1
c = 16.2970 (13) ÅT = 295 K
β = 116.949 (2)°Block, pale yellow
V = 1191.59 (15) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
MacScience DIPLabo 32001
diffractometer
1690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm-1h = 1212
ω scansk = 87
3643 measured reflectionsl = 1919
1945 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.089P)2 + 0.3587P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1945 reflectionsΔρmax = 0.56 e Å3
156 parametersΔρmin = 0.33 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.069 (8)
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
xyzUiso*/Ueq
Cl10.11345 (8)0.52861 (12)0.22626 (5)0.0852 (3)
O90.64836 (17)0.8601 (2)0.04667 (11)0.0652 (6)
O120.48953 (17)0.8234 (2)0.12905 (10)0.0627 (6)
C30.2408 (3)0.4630 (4)0.24512 (17)0.0731 (10)
C40.3222 (2)0.6153 (3)0.09320 (14)0.0495 (7)
C50.3443 (3)0.5725 (3)0.16814 (14)0.0555 (8)
C60.4674 (3)0.6364 (3)0.16955 (15)0.0611 (9)
C70.5657 (2)0.7318 (3)0.09872 (16)0.0594 (9)
C80.5452 (2)0.7703 (3)0.02238 (14)0.0501 (7)
C100.4193 (2)0.7145 (3)0.02005 (13)0.0458 (7)
C110.3941 (2)0.7596 (3)0.05881 (14)0.0482 (7)
C130.2516 (2)0.7303 (3)0.05619 (14)0.0473 (7)
C140.2466 (2)0.6508 (3)0.13113 (14)0.0498 (7)
C150.1178 (3)0.6325 (3)0.13265 (16)0.0549 (8)
C160.0071 (3)0.6940 (4)0.06289 (18)0.0636 (9)
C170.0010 (3)0.7751 (4)0.01064 (18)0.0681 (9)
C180.1258 (3)0.7913 (4)0.01523 (15)0.0606 (8)
H3A0.184400.397400.223800.1100*
H3B0.292700.387100.265400.1100*
H3C0.179200.534400.295400.1100*
H40.239700.576700.091300.0590*
H60.483200.613500.220200.0730*
H70.647200.771200.101800.0710*
H90.624900.875500.087800.0980*
H140.330100.610500.179800.0600*
H160.093700.681400.065100.0760*
H170.084300.819400.057800.0820*
H180.127700.843100.066100.0730*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0878 (6)0.1076 (7)0.0795 (5)0.0073 (4)0.0548 (5)0.0179 (4)
O90.0573 (10)0.0803 (13)0.0647 (10)0.0086 (8)0.0336 (8)0.0034 (8)
O120.0608 (10)0.0826 (13)0.0497 (9)0.0111 (8)0.0295 (8)0.0127 (8)
C30.0878 (19)0.081 (2)0.0503 (13)0.0038 (14)0.0312 (13)0.0085 (12)
C40.0568 (13)0.0505 (14)0.0467 (11)0.0028 (9)0.0284 (10)0.0027 (9)
C50.0703 (15)0.0579 (15)0.0420 (11)0.0133 (11)0.0287 (10)0.0057 (9)
C60.0718 (15)0.0775 (18)0.0459 (12)0.0235 (12)0.0370 (11)0.0139 (11)
C70.0586 (14)0.0754 (17)0.0590 (13)0.0117 (11)0.0395 (11)0.0158 (11)
C80.0505 (12)0.0554 (14)0.0501 (11)0.0075 (9)0.0277 (9)0.0101 (9)
C100.0526 (12)0.0479 (13)0.0440 (10)0.0059 (9)0.0282 (9)0.0058 (8)
C110.0538 (12)0.0506 (13)0.0455 (11)0.0016 (9)0.0271 (9)0.0002 (9)
C130.0530 (12)0.0508 (13)0.0449 (10)0.0015 (9)0.0281 (9)0.0046 (9)
C140.0524 (12)0.0550 (14)0.0462 (11)0.0007 (9)0.0259 (9)0.0029 (9)
C150.0605 (14)0.0582 (15)0.0566 (13)0.0049 (10)0.0358 (11)0.0035 (10)
C160.0548 (14)0.0663 (17)0.0792 (16)0.0018 (11)0.0387 (13)0.0023 (12)
C170.0543 (14)0.0791 (18)0.0683 (15)0.0117 (12)0.0256 (11)0.0120 (13)
C180.0633 (14)0.0686 (16)0.0548 (13)0.0094 (11)0.0310 (11)0.0092 (11)
Geometric parameters (Å, º) top
Cl1—C151.747 (3)C14—C151.369 (4)
O9—C81.351 (3)C15—C161.375 (4)
O12—C111.234 (3)C16—C171.383 (4)
O9—H90.8208C17—C181.371 (5)
C3—C51.500 (4)C3—H3A0.9592
C4—C101.400 (3)C3—H3B0.9596
C4—C51.383 (3)C3—H3C0.9596
C5—C61.394 (5)C4—H40.9299
C6—C71.369 (3)C6—H60.9300
C7—C81.388 (3)C7—H70.9309
C8—C101.407 (3)C14—H140.9304
C10—C111.468 (3)C16—H160.9301
C11—C131.493 (3)C17—H170.9302
C13—C181.390 (3)C18—H180.9311
C13—C141.393 (3)
O9···O122.585 (3)C13···H42.6392
O9···C10i3.389 (3)C14···H3Cii2.9605
O9···C11i3.363 (3)C15···H3Cii2.8099
O12···O92.585 (3)C16···H3Cii3.0943
O12···C6ii3.408 (3)C18···H42.6690
O12···H142.7396H3A···H42.4149
O12···H3Biii2.8748H3B···H62.5170
O12···H91.8701H3B···O12iii2.8748
O12···H6ii2.5361H3C···C14iv2.9605
C4···C8iii3.494 (3)H3C···C15iv2.8099
C4···C183.182 (4)H3C···C16iv3.0943
C4···C10iii3.588 (3)H4···C132.6392
C6···C14iv3.445 (3)H4···C182.6690
C6···C14iii3.568 (4)H4···H3A2.4149
C6···C11iii3.548 (3)H4···H182.5156
C6···O12iv3.408 (3)H6···H3B2.5170
C8···C4iii3.494 (3)H6···H14iii2.4835
C10···C4iii3.588 (3)H6···O12iv2.5361
C10···O9i3.389 (3)H7···H17vii2.5985
C11···C6iii3.548 (3)H9···O121.8701
C11···O9i3.363 (3)H9···C112.4218
C14···C6iii3.568 (4)H14···O122.7396
C14···C6ii3.445 (3)H14···C6iii2.9305
C17···C17v3.535 (4)H14···H6iii2.4836
C18···C43.182 (4)H14···C6ii2.9693
C3···H17vi3.0811H17···H7viii2.5985
C4···H182.8890H17···C3ix3.0811
C6···H14iv2.9693H18···C42.8890
C6···H14iii2.9305H18···C102.9738
C10···H182.9738H18···H42.5156
C11···H92.4218
C8—O9—H9109.47C15—C16—C17118.5 (3)
C5—C4—C10122.5 (2)C16—C17—C18121.1 (3)
C3—C5—C4122.0 (3)C13—C18—C17119.9 (2)
C3—C5—C6121.0 (2)C5—C3—H3A109.49
C4—C5—C6117.0 (2)C5—C3—H3B109.45
C5—C6—C7122.0 (2)C5—C3—H3C109.48
C6—C7—C8120.7 (2)H3A—C3—H3B109.43
O9—C8—C7117.9 (2)H3A—C3—H3C109.50
C7—C8—C10119.0 (2)H3B—C3—H3C109.47
O9—C8—C10123.05 (19)C5—C4—H4118.77
C4—C10—C8118.56 (19)C10—C4—H4118.69
C8—C10—C11119.50 (19)C5—C6—H6118.96
C4—C10—C11121.9 (2)C7—C6—H6118.99
O12—C11—C13118.0 (2)C6—C7—H7119.59
C10—C11—C13120.87 (19)C8—C7—H7119.68
O12—C11—C10121.2 (2)C13—C14—H14120.27
C11—C13—C18121.9 (2)C15—C14—H14120.26
C14—C13—C18119.3 (2)C15—C16—H16120.78
C11—C13—C14118.58 (19)C17—C16—H16120.77
C13—C14—C15119.5 (2)C16—C17—H17119.48
Cl1—C15—C16119.5 (3)C18—C17—H17119.42
C14—C15—C16121.7 (2)C13—C18—H18120.01
Cl1—C15—C14118.72 (19)C17—C18—H18120.10
C10—C4—C5—C61.6 (4)C8—C10—C11—O1210.8 (3)
C10—C4—C5—C3178.7 (2)C10—C11—C13—C14132.4 (2)
C5—C4—C10—C11179.7 (2)C10—C11—C13—C1852.5 (3)
C5—C4—C10—C81.0 (3)O12—C11—C13—C18127.2 (3)
C4—C5—C6—C72.5 (4)O12—C11—C13—C1447.9 (3)
C3—C5—C6—C7177.8 (2)C18—C13—C14—C150.7 (4)
C5—C6—C7—C80.7 (4)C11—C13—C14—C15175.9 (2)
C6—C7—C8—O9177.8 (2)C11—C13—C18—C17174.0 (3)
C6—C7—C8—C102.1 (3)C14—C13—C18—C171.0 (4)
O9—C8—C10—C4177.0 (2)C13—C14—C15—Cl1178.75 (18)
C7—C8—C10—C11177.9 (2)C13—C14—C15—C161.5 (4)
O9—C8—C10—C112.3 (3)C14—C15—C16—C170.5 (4)
C7—C8—C10—C42.9 (3)Cl1—C15—C16—C17179.7 (2)
C4—C10—C11—O12168.5 (2)C15—C16—C17—C181.3 (4)
C8—C10—C11—C13168.9 (2)C16—C17—C18—C132.0 (4)
C4—C10—C11—C1311.8 (3)
Symmetry codes: (i) x+1, y+2, z; (ii) x, y+3/2, z+1/2; (iii) x+1, y+1, z; (iv) x, y+3/2, z1/2; (v) x, y+2, z; (vi) x, y1/2, z1/2; (vii) x+1, y, z; (viii) x1, y, z; (ix) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9···O120.821.872.585 (3)145
C6—H6···O12iv0.932.543.408 (3)156
Symmetry code: (iv) x, y+3/2, z1/2.
 

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