Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013651/wn2022sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013651/wn2022Isup2.hkl
Contains datablock I

CCDC reference: 610918

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

Computing details top

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 top
Crystal data top
C14H11ClO2Z = 2
Mr = 246.68F(000) = 256
Triclinic, P1Dx = 1.375 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.362 (8) ÅCell parameters from 3083 reflections
b = 7.44 (1) Åθ = 2.8–25.0°
c = 11.001 (14) ŵ = 0.31 mm1
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) Å3
Data collection top
MacScience DIPLabo 32001
diffractometer
1610 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
Detector resolution: 10.0 pixels mm-1h = 88
ω scansk = 88
3083 measured reflectionsl = 1313
1898 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)] = 0.046H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0905P)2 + 0.1264P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1898 reflectionsΔρmax = 0.24 e Å3
156 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.14 (2)
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
Cl170.24078 (11)0.33354 (12)0.50699 (6)0.0938 (4)
O151.2327 (2)0.3053 (2)0.00083 (16)0.0692 (6)
O161.0605 (2)0.2804 (3)0.21162 (16)0.0738 (7)
C10.7673 (3)0.1617 (3)0.14520 (19)0.0529 (7)
C20.9251 (3)0.1934 (3)0.2173 (2)0.0611 (8)
C31.0764 (3)0.2424 (3)0.1684 (2)0.0623 (8)
C41.0773 (3)0.2633 (3)0.0437 (2)0.0538 (7)
C50.9174 (3)0.2421 (3)0.03186 (18)0.0481 (6)
C60.7666 (3)0.1887 (3)0.02159 (18)0.0485 (7)
C70.9168 (3)0.2693 (3)0.1637 (2)0.0537 (7)
C80.7424 (3)0.2842 (3)0.24424 (18)0.0511 (7)
C90.7468 (4)0.1969 (4)0.3579 (2)0.0646 (8)
C100.5925 (4)0.2098 (4)0.4381 (2)0.0700 (9)
C110.4350 (3)0.3152 (3)0.4061 (2)0.0605 (8)
C120.4283 (3)0.4065 (3)0.2950 (2)0.0563 (7)
C130.5826 (3)0.3885 (3)0.21368 (18)0.0527 (7)
C140.6060 (3)0.0993 (4)0.1999 (2)0.0670 (8)
H20.927400.180800.301300.0730*
H31.179400.261800.219100.0750*
H60.662000.170800.028000.0580*
H90.854700.129200.380100.0780*
H100.594700.148100.513000.0840*
H120.322000.478900.274900.0680*
H130.578600.447200.137800.0630*
H14A0.640900.018900.232900.1010*
H14B0.566400.182800.263700.1010*
H14C0.507400.094100.138000.1010*
H151.217100.313900.075100.1040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl170.0839 (6)0.1296 (8)0.0675 (5)0.0298 (5)0.0297 (4)0.0156 (4)
O150.0476 (9)0.0809 (12)0.0802 (12)0.0177 (8)0.0053 (8)0.0036 (9)
O160.0541 (10)0.1016 (14)0.0687 (11)0.0167 (9)0.0072 (8)0.0154 (9)
C10.0559 (12)0.0529 (12)0.0486 (11)0.0038 (9)0.0005 (9)0.0017 (9)
C20.0672 (14)0.0654 (15)0.0462 (11)0.0010 (11)0.0071 (10)0.0035 (9)
C30.0530 (13)0.0688 (15)0.0612 (14)0.0054 (11)0.0139 (10)0.0080 (10)
C40.0455 (11)0.0483 (12)0.0659 (13)0.0057 (9)0.0041 (9)0.0032 (9)
C50.0476 (11)0.0445 (11)0.0514 (11)0.0069 (8)0.0029 (8)0.0002 (8)
C60.0477 (11)0.0473 (12)0.0495 (11)0.0068 (9)0.0044 (8)0.0014 (8)
C70.0484 (11)0.0556 (13)0.0586 (13)0.0119 (9)0.0013 (9)0.0070 (9)
C80.0528 (12)0.0553 (13)0.0466 (11)0.0127 (9)0.0003 (8)0.0076 (8)
C90.0690 (15)0.0748 (16)0.0494 (12)0.0051 (12)0.0061 (10)0.0014 (10)
C100.0853 (18)0.0831 (18)0.0423 (11)0.0171 (14)0.0003 (11)0.0026 (11)
C110.0638 (13)0.0701 (15)0.0496 (12)0.0212 (11)0.0095 (10)0.0130 (10)
C120.0525 (12)0.0608 (13)0.0567 (12)0.0126 (10)0.0012 (9)0.0089 (10)
C130.0548 (12)0.0580 (13)0.0463 (11)0.0135 (10)0.0002 (9)0.0007 (9)
C140.0699 (15)0.0780 (16)0.0542 (13)0.0104 (12)0.0067 (11)0.0063 (11)
Geometric parameters (Å, º) top
Cl17—C111.736 (3)C9—C101.380 (4)
O15—C41.353 (3)C10—C111.379 (4)
O16—C71.230 (3)C11—C121.380 (4)
O15—H150.8198C12—C131.387 (4)
C1—C61.381 (3)C2—H20.9305
C1—C141.501 (4)C3—H30.9298
C1—C21.396 (4)C6—H60.9301
C2—C31.367 (4)C9—H90.9307
C3—C41.386 (4)C10—H100.9304
C4—C51.411 (4)C12—H120.9300
C5—C61.400 (4)C13—H130.9302
C5—C71.470 (4)C14—H14A0.9598
C7—C81.498 (4)C14—H14B0.9599
C8—C131.384 (4)C14—H14C0.9602
C8—C91.391 (4)
Cl17···H3i3.0524C12···H14Bvi3.0686
O15···O162.569 (4)C13···H62.6331
O16···C12ii3.182 (5)H3···Cl17viii3.0524
O16···O152.569 (4)H6···C82.6816
O15···H13iii2.7892H6···C132.6331
O15···H14Cii2.7897H6···H132.4078
O16···H92.6188H6···H14C2.3458
O16···H12ii2.7116H9···O162.6188
O16···H151.8520H10···H14Bix2.4686
O16···H14Aiv2.7666H12···O16v2.7116
C2···C7iv3.539 (6)H12···C1vi3.0125
C4···C6iv3.486 (6)H12···C2vi2.9367
C6···C133.155 (5)H13···C52.9376
C6···C4iv3.486 (6)H13···C62.8058
C7···C2iv3.539 (6)H13···H62.4078
C12···O16v3.182 (5)H13···O15iii2.7892
C13···C63.155 (5)H14A···O16iv2.7666
C1···H12vi3.0125H14A···C11vii3.0894
C2···H12vi2.9367H14A···C12vii3.0967
C5···H132.9376H14B···H10x2.4686
C6···H132.8058H14B···C12vi3.0686
C7···H152.4044H14C···O15v2.7897
C8···H62.6816H14C···H62.3458
C11···H14Avii3.0894H15···O161.8520
C12···H14Avii3.0967H15···C72.4044
C4—O15—H15109.47C10—C11—C12121.3 (2)
C2—C1—C14121.28 (19)C11—C12—C13119.0 (2)
C6—C1—C14121.5 (2)C8—C13—C12120.70 (19)
C2—C1—C6117.2 (2)C1—C2—H2118.99
C1—C2—C3122.1 (2)C3—C2—H2118.92
C2—C3—C4120.4 (2)C2—C3—H3119.79
O15—C4—C3118.2 (2)C4—C3—H3119.78
O15—C4—C5122.40 (19)C1—C6—H6118.74
C3—C4—C5119.4 (2)C5—C6—H6118.80
C4—C5—C6118.27 (19)C8—C9—H9119.77
C4—C5—C7119.3 (2)C10—C9—H9119.67
C6—C5—C7122.33 (19)C9—C10—H10120.37
C1—C6—C5122.5 (2)C11—C10—H10120.34
O16—C7—C8117.7 (2)C11—C12—H12120.57
C5—C7—C8121.46 (19)C13—C12—H12120.48
O16—C7—C5120.8 (2)C8—C13—H13119.67
C7—C8—C13123.12 (19)C12—C13—H13119.63
C9—C8—C13119.2 (2)C1—C14—H14A109.50
C7—C8—C9117.6 (2)C1—C14—H14B109.48
C8—C9—C10120.6 (3)C1—C14—H14C109.46
C9—C10—C11119.3 (2)H14A—C14—H14B109.50
Cl17—C11—C10119.58 (18)H14A—C14—H14C109.44
Cl17—C11—C12119.15 (17)H14B—C14—H14C109.45
C2—C1—C6—C51.3 (3)C6—C5—C7—O16165.4 (2)
C14—C1—C6—C5178.2 (2)C5—C7—C8—C9139.1 (2)
C6—C1—C2—C32.5 (3)C5—C7—C8—C1344.8 (3)
C14—C1—C2—C3177.0 (2)O16—C7—C8—C13135.3 (2)
C1—C2—C3—C40.3 (3)O16—C7—C8—C940.8 (3)
C2—C3—C4—O15177.6 (2)C7—C8—C13—C12175.9 (2)
C2—C3—C4—C53.0 (3)C7—C8—C9—C10178.0 (2)
O15—C4—C5—C6176.5 (2)C13—C8—C9—C101.8 (4)
C3—C4—C5—C7178.3 (2)C9—C8—C13—C120.1 (3)
O15—C4—C5—C71.1 (3)C8—C9—C10—C112.1 (4)
C3—C4—C5—C64.1 (3)C9—C10—C11—C120.6 (4)
C4—C5—C6—C12.0 (3)C9—C10—C11—Cl17179.5 (2)
C4—C5—C7—C8168.0 (2)Cl17—C11—C12—C13178.70 (17)
C7—C5—C6—C1179.5 (2)C10—C11—C12—C131.2 (3)
C4—C5—C7—O1612.1 (3)C11—C12—C13—C81.5 (3)
C6—C5—C7—C814.6 (3)
Symmetry codes: (i) x1, y, z+1; (ii) x+1, y, z; (iii) x+2, y+1, z; (iv) x+2, y, z; (v) x1, y, z; (vi) x+1, y+1, z; (vii) x+1, y, z; (viii) x+1, y, z1; (ix) x, y, z+1; (x) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15—H15···O160.821.852.569 (4)145
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds