In the title compound, C
14H
11ClO
2, 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
CCDC reference: 610918
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
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) Å3 | |
Data collection top
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 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)] = 0.046 | H-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 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 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 | |
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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···H3i | 3.0524 | C12···H14Bvi | 3.0686 |
O15···O16 | 2.569 (4) | C13···H6 | 2.6331 |
O16···C12ii | 3.182 (5) | H3···Cl17viii | 3.0524 |
O16···O15 | 2.569 (4) | H6···C8 | 2.6816 |
O15···H13iii | 2.7892 | H6···C13 | 2.6331 |
O15···H14Cii | 2.7897 | H6···H13 | 2.4078 |
O16···H9 | 2.6188 | H6···H14C | 2.3458 |
O16···H12ii | 2.7116 | H9···O16 | 2.6188 |
O16···H15 | 1.8520 | H10···H14Bix | 2.4686 |
O16···H14Aiv | 2.7666 | H12···O16v | 2.7116 |
C2···C7iv | 3.539 (6) | H12···C1vi | 3.0125 |
C4···C6iv | 3.486 (6) | H12···C2vi | 2.9367 |
C6···C13 | 3.155 (5) | H13···C5 | 2.9376 |
C6···C4iv | 3.486 (6) | H13···C6 | 2.8058 |
C7···C2iv | 3.539 (6) | H13···H6 | 2.4078 |
C12···O16v | 3.182 (5) | H13···O15iii | 2.7892 |
C13···C6 | 3.155 (5) | H14A···O16iv | 2.7666 |
C1···H12vi | 3.0125 | H14A···C11vii | 3.0894 |
C2···H12vi | 2.9367 | H14A···C12vii | 3.0967 |
C5···H13 | 2.9376 | H14B···H10x | 2.4686 |
C6···H13 | 2.8058 | H14B···C12vi | 3.0686 |
C7···H15 | 2.4044 | H14C···O15v | 2.7897 |
C8···H6 | 2.6816 | H14C···H6 | 2.3458 |
C11···H14Avii | 3.0894 | H15···O16 | 1.8520 |
C12···H14Avii | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15···O16 | 0.82 | 1.85 | 2.569 (4) | 145 |