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In the title compound, C15H14ClO2, the dihedral angle between the two benzene rings is 57.37 (12)°.
Supporting information
CCDC reference: 219251
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C14H11ClO2 | F(000) = 512 |
Mr = 246.68 | Dx = 1.375 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3643 reflections |
a = 10.4850 (9) Å | θ = 2.3–25.0° |
b = 7.8230 (4) Å | µ = 0.31 mm−1 |
c = 16.2970 (13) Å | T = 295 K |
β = 116.949 (2)° | Block, pale yellow |
V = 1191.59 (15) Å3 | 0.3 × 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 tube | Rint = 0.017 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
Detector resolution: 10.0 pixels mm-1 | h = −12→12 |
ω scans | k = −8→7 |
3643 measured reflections | l = −19→19 |
1945 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)] = 0.049 | H-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 reflections | Δρmax = 0.56 e Å−3 |
156 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.11345 (8) | 0.52861 (12) | 0.22626 (5) | 0.0852 (3) | |
O9 | 0.64836 (17) | 0.8601 (2) | 0.04667 (11) | 0.0652 (6) | |
O12 | 0.48953 (17) | 0.8234 (2) | 0.12905 (10) | 0.0627 (6) | |
C3 | 0.2408 (3) | 0.4630 (4) | −0.24512 (17) | 0.0731 (10) | |
C4 | 0.3222 (2) | 0.6153 (3) | −0.09320 (14) | 0.0495 (7) | |
C5 | 0.3443 (3) | 0.5725 (3) | −0.16814 (14) | 0.0555 (8) | |
C6 | 0.4674 (3) | 0.6364 (3) | −0.16955 (15) | 0.0611 (9) | |
C7 | 0.5657 (2) | 0.7318 (3) | −0.09872 (16) | 0.0594 (9) | |
C8 | 0.5452 (2) | 0.7703 (3) | −0.02238 (14) | 0.0501 (7) | |
C10 | 0.4193 (2) | 0.7145 (3) | −0.02005 (13) | 0.0458 (7) | |
C11 | 0.3941 (2) | 0.7596 (3) | 0.05881 (14) | 0.0482 (7) | |
C13 | 0.2516 (2) | 0.7303 (3) | 0.05619 (14) | 0.0473 (7) | |
C14 | 0.2466 (2) | 0.6508 (3) | 0.13113 (14) | 0.0498 (7) | |
C15 | 0.1178 (3) | 0.6325 (3) | 0.13265 (16) | 0.0549 (8) | |
C16 | −0.0071 (3) | 0.6940 (4) | 0.06289 (18) | 0.0636 (9) | |
C17 | −0.0010 (3) | 0.7751 (4) | −0.01064 (18) | 0.0681 (9) | |
C18 | 0.1258 (3) | 0.7913 (4) | −0.01523 (15) | 0.0606 (8) | |
H3A | 0.18440 | 0.39740 | −0.22380 | 0.1100* | |
H3B | 0.29270 | 0.38710 | −0.26540 | 0.1100* | |
H3C | 0.17920 | 0.53440 | −0.29540 | 0.1100* | |
H4 | 0.23970 | 0.57670 | −0.09130 | 0.0590* | |
H6 | 0.48320 | 0.61350 | −0.22020 | 0.0730* | |
H7 | 0.64720 | 0.77120 | −0.10180 | 0.0710* | |
H9 | 0.62490 | 0.87550 | 0.08780 | 0.0980* | |
H14 | 0.33010 | 0.61050 | 0.17980 | 0.0600* | |
H16 | −0.09370 | 0.68140 | 0.06510 | 0.0760* | |
H17 | −0.08430 | 0.81940 | −0.05780 | 0.0820* | |
H18 | 0.12770 | 0.84310 | −0.06610 | 0.0730* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0878 (6) | 0.1076 (7) | 0.0795 (5) | −0.0073 (4) | 0.0548 (5) | 0.0179 (4) |
O9 | 0.0573 (10) | 0.0803 (13) | 0.0647 (10) | −0.0086 (8) | 0.0336 (8) | −0.0034 (8) |
O12 | 0.0608 (10) | 0.0826 (13) | 0.0497 (9) | −0.0111 (8) | 0.0295 (8) | −0.0127 (8) |
C3 | 0.0878 (19) | 0.081 (2) | 0.0503 (13) | 0.0038 (14) | 0.0312 (13) | −0.0085 (12) |
C4 | 0.0568 (13) | 0.0505 (14) | 0.0467 (11) | 0.0028 (9) | 0.0284 (10) | 0.0027 (9) |
C5 | 0.0703 (15) | 0.0579 (15) | 0.0420 (11) | 0.0133 (11) | 0.0287 (10) | 0.0057 (9) |
C6 | 0.0718 (15) | 0.0775 (18) | 0.0459 (12) | 0.0235 (12) | 0.0370 (11) | 0.0139 (11) |
C7 | 0.0586 (14) | 0.0754 (17) | 0.0590 (13) | 0.0117 (11) | 0.0395 (11) | 0.0158 (11) |
C8 | 0.0505 (12) | 0.0554 (14) | 0.0501 (11) | 0.0075 (9) | 0.0277 (9) | 0.0101 (9) |
C10 | 0.0526 (12) | 0.0479 (13) | 0.0440 (10) | 0.0059 (9) | 0.0282 (9) | 0.0058 (8) |
C11 | 0.0538 (12) | 0.0506 (13) | 0.0455 (11) | 0.0016 (9) | 0.0271 (9) | −0.0002 (9) |
C13 | 0.0530 (12) | 0.0508 (13) | 0.0449 (10) | 0.0015 (9) | 0.0281 (9) | −0.0046 (9) |
C14 | 0.0524 (12) | 0.0550 (14) | 0.0462 (11) | 0.0007 (9) | 0.0259 (9) | −0.0029 (9) |
C15 | 0.0605 (14) | 0.0582 (15) | 0.0566 (13) | −0.0049 (10) | 0.0358 (11) | −0.0035 (10) |
C16 | 0.0548 (14) | 0.0663 (17) | 0.0792 (16) | −0.0018 (11) | 0.0387 (13) | −0.0023 (12) |
C17 | 0.0543 (14) | 0.0791 (18) | 0.0683 (15) | 0.0117 (12) | 0.0256 (11) | 0.0120 (13) |
C18 | 0.0633 (14) | 0.0686 (16) | 0.0548 (13) | 0.0094 (11) | 0.0310 (11) | 0.0092 (11) |
Geometric parameters (Å, º) top
Cl1—C15 | 1.747 (3) | C14—C15 | 1.369 (4) |
O9—C8 | 1.351 (3) | C15—C16 | 1.375 (4) |
O12—C11 | 1.234 (3) | C16—C17 | 1.383 (4) |
O9—H9 | 0.8208 | C17—C18 | 1.371 (5) |
C3—C5 | 1.500 (4) | C3—H3A | 0.9592 |
C4—C10 | 1.400 (3) | C3—H3B | 0.9596 |
C4—C5 | 1.383 (3) | C3—H3C | 0.9596 |
C5—C6 | 1.394 (5) | C4—H4 | 0.9299 |
C6—C7 | 1.369 (3) | C6—H6 | 0.9300 |
C7—C8 | 1.388 (3) | C7—H7 | 0.9309 |
C8—C10 | 1.407 (3) | C14—H14 | 0.9304 |
C10—C11 | 1.468 (3) | C16—H16 | 0.9301 |
C11—C13 | 1.493 (3) | C17—H17 | 0.9302 |
C13—C18 | 1.390 (3) | C18—H18 | 0.9311 |
C13—C14 | 1.393 (3) | | |
| | | |
O9···O12 | 2.585 (3) | C13···H4 | 2.6392 |
O9···C10i | 3.389 (3) | C14···H3Cii | 2.9605 |
O9···C11i | 3.363 (3) | C15···H3Cii | 2.8099 |
O12···O9 | 2.585 (3) | C16···H3Cii | 3.0943 |
O12···C6ii | 3.408 (3) | C18···H4 | 2.6690 |
O12···H14 | 2.7396 | H3A···H4 | 2.4149 |
O12···H3Biii | 2.8748 | H3B···H6 | 2.5170 |
O12···H9 | 1.8701 | H3B···O12iii | 2.8748 |
O12···H6ii | 2.5361 | H3C···C14iv | 2.9605 |
C4···C8iii | 3.494 (3) | H3C···C15iv | 2.8099 |
C4···C18 | 3.182 (4) | H3C···C16iv | 3.0943 |
C4···C10iii | 3.588 (3) | H4···C13 | 2.6392 |
C6···C14iv | 3.445 (3) | H4···C18 | 2.6690 |
C6···C14iii | 3.568 (4) | H4···H3A | 2.4149 |
C6···C11iii | 3.548 (3) | H4···H18 | 2.5156 |
C6···O12iv | 3.408 (3) | H6···H3B | 2.5170 |
C8···C4iii | 3.494 (3) | H6···H14iii | 2.4835 |
C10···C4iii | 3.588 (3) | H6···O12iv | 2.5361 |
C10···O9i | 3.389 (3) | H7···H17vii | 2.5985 |
C11···C6iii | 3.548 (3) | H9···O12 | 1.8701 |
C11···O9i | 3.363 (3) | H9···C11 | 2.4218 |
C14···C6iii | 3.568 (4) | H14···O12 | 2.7396 |
C14···C6ii | 3.445 (3) | H14···C6iii | 2.9305 |
C17···C17v | 3.535 (4) | H14···H6iii | 2.4836 |
C18···C4 | 3.182 (4) | H14···C6ii | 2.9693 |
C3···H17vi | 3.0811 | H17···H7viii | 2.5985 |
C4···H18 | 2.8890 | H17···C3ix | 3.0811 |
C6···H14iv | 2.9693 | H18···C4 | 2.8890 |
C6···H14iii | 2.9305 | H18···C10 | 2.9738 |
C10···H18 | 2.9738 | H18···H4 | 2.5156 |
C11···H9 | 2.4218 | | |
| | | |
C8—O9—H9 | 109.47 | C15—C16—C17 | 118.5 (3) |
C5—C4—C10 | 122.5 (2) | C16—C17—C18 | 121.1 (3) |
C3—C5—C4 | 122.0 (3) | C13—C18—C17 | 119.9 (2) |
C3—C5—C6 | 121.0 (2) | C5—C3—H3A | 109.49 |
C4—C5—C6 | 117.0 (2) | C5—C3—H3B | 109.45 |
C5—C6—C7 | 122.0 (2) | C5—C3—H3C | 109.48 |
C6—C7—C8 | 120.7 (2) | H3A—C3—H3B | 109.43 |
O9—C8—C7 | 117.9 (2) | H3A—C3—H3C | 109.50 |
C7—C8—C10 | 119.0 (2) | H3B—C3—H3C | 109.47 |
O9—C8—C10 | 123.05 (19) | C5—C4—H4 | 118.77 |
C4—C10—C8 | 118.56 (19) | C10—C4—H4 | 118.69 |
C8—C10—C11 | 119.50 (19) | C5—C6—H6 | 118.96 |
C4—C10—C11 | 121.9 (2) | C7—C6—H6 | 118.99 |
O12—C11—C13 | 118.0 (2) | C6—C7—H7 | 119.59 |
C10—C11—C13 | 120.87 (19) | C8—C7—H7 | 119.68 |
O12—C11—C10 | 121.2 (2) | C13—C14—H14 | 120.27 |
C11—C13—C18 | 121.9 (2) | C15—C14—H14 | 120.26 |
C14—C13—C18 | 119.3 (2) | C15—C16—H16 | 120.78 |
C11—C13—C14 | 118.58 (19) | C17—C16—H16 | 120.77 |
C13—C14—C15 | 119.5 (2) | C16—C17—H17 | 119.48 |
Cl1—C15—C16 | 119.5 (3) | C18—C17—H17 | 119.42 |
C14—C15—C16 | 121.7 (2) | C13—C18—H18 | 120.01 |
Cl1—C15—C14 | 118.72 (19) | C17—C18—H18 | 120.10 |
| | | |
C10—C4—C5—C6 | −1.6 (4) | C8—C10—C11—O12 | −10.8 (3) |
C10—C4—C5—C3 | 178.7 (2) | C10—C11—C13—C14 | 132.4 (2) |
C5—C4—C10—C11 | 179.7 (2) | C10—C11—C13—C18 | −52.5 (3) |
C5—C4—C10—C8 | −1.0 (3) | O12—C11—C13—C18 | 127.2 (3) |
C4—C5—C6—C7 | 2.5 (4) | O12—C11—C13—C14 | −47.9 (3) |
C3—C5—C6—C7 | −177.8 (2) | C18—C13—C14—C15 | 0.7 (4) |
C5—C6—C7—C8 | −0.7 (4) | C11—C13—C14—C15 | 175.9 (2) |
C6—C7—C8—O9 | 177.8 (2) | C11—C13—C18—C17 | −174.0 (3) |
C6—C7—C8—C10 | −2.1 (3) | C14—C13—C18—C17 | 1.0 (4) |
O9—C8—C10—C4 | −177.0 (2) | C13—C14—C15—Cl1 | 178.75 (18) |
C7—C8—C10—C11 | −177.9 (2) | C13—C14—C15—C16 | −1.5 (4) |
O9—C8—C10—C11 | 2.3 (3) | C14—C15—C16—C17 | 0.5 (4) |
C7—C8—C10—C4 | 2.9 (3) | Cl1—C15—C16—C17 | −179.7 (2) |
C4—C10—C11—O12 | 168.5 (2) | C15—C16—C17—C18 | 1.3 (4) |
C8—C10—C11—C13 | 168.9 (2) | C16—C17—C18—C13 | −2.0 (4) |
C4—C10—C11—C13 | −11.8 (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, z−1/2; (v) −x, −y+2, −z; (vi) −x, y−1/2, −z−1/2; (vii) x+1, y, z; (viii) x−1, y, z; (ix) −x, y+1/2, −z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O12 | 0.82 | 1.87 | 2.585 (3) | 145 |
C6—H6···O12iv | 0.93 | 2.54 | 3.408 (3) | 156 |
Symmetry code: (iv) x, −y+3/2, z−1/2. |
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