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The crystal structure determination of the title compound, C
12H
10O, has been reported previously [Gupta & Gupta (1975).
Acta Cryst. B
31, 7–9], with an
R value of 0.078. The results reported here are in agreement with the literature data but a more precise molecular geometry is obtained (σ on C—C = 0.002 Å). Intermolecular O—H
O hydrogen bonds connect molecules into a chain running parallel to the [010] direction. This chain is reinforced by two C—H
π interactions.
Supporting information
CCDC reference: 640406
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.100
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 6.81 su
0 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and DIAMOND (Crystal Impact, 2001); software used to prepare material for publication: SHELXL97.
Crystal data top
C12H10O | F(000) = 360 |
Mr = 170.20 | Dx = 1.295 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4587 reflections |
a = 12.9585 (11) Å | θ = 4.2–25.0° |
b = 4.9326 (5) Å | µ = 0.08 mm−1 |
c = 15.6749 (19) Å | T = 290 K |
β = 119.398 (9)° | Plate, translucent white |
V = 872.91 (16) Å3 | 0.49 × 0.28 × 0.09 mm |
Z = 4 | |
Data collection top
Oxford Diffraction Xcalibur3 CCD diffractometer | 1501 independent reflections |
Radiation source: fine-focus sealed tube | 1267 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 25.0°, θmin = 4.2° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005) | h = −15→14 |
Tmin = 0.968, Tmax = 0.991 | k = −5→2 |
4587 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1377P] where P = (Fo2 + 2Fc2)/3 |
1501 reflections | (Δ/σ)max = 0.002 |
130 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 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 | |
O1 | 0.05537 (9) | 0.7036 (2) | 0.26686 (8) | 0.0458 (3) | |
C1 | 0.24939 (11) | 0.9417 (2) | 0.19722 (10) | 0.0364 (3) | |
C2 | 0.23950 (11) | 0.8436 (3) | 0.27663 (9) | 0.0369 (3) | |
C3 | 0.31334 (13) | 0.9457 (3) | 0.36760 (11) | 0.0477 (4) | |
H3 | 0.3091 | 0.8845 | 0.4219 | 0.057* | |
C4 | 0.39686 (12) | 1.1477 (3) | 0.37760 (12) | 0.0536 (4) | |
H4 | 0.4468 | 1.2185 | 0.4395 | 0.064* | |
C5 | 0.40664 (13) | 1.2417 (3) | 0.30015 (13) | 0.0554 (4) | |
H5 | 0.4628 | 1.3733 | 0.3099 | 0.066* | |
C6 | 0.33102 (12) | 1.1391 (3) | 0.20415 (12) | 0.0452 (4) | |
C7 | 0.32811 (15) | 1.2141 (3) | 0.11561 (14) | 0.0602 (5) | |
H7 | 0.3802 | 1.3446 | 0.1160 | 0.072* | |
C8 | 0.24848 (17) | 1.0938 (4) | 0.02979 (14) | 0.0630 (5) | |
H8 | 0.2480 | 1.1448 | −0.0275 | 0.076* | |
C9 | 0.16691 (15) | 0.8957 (3) | 0.02410 (11) | 0.0536 (4) | |
H9 | 0.1140 | 0.8184 | −0.0358 | 0.064* | |
C10 | 0.16669 (12) | 0.8192 (3) | 0.10747 (10) | 0.0405 (3) | |
C11 | 0.09385 (13) | 0.6190 (3) | 0.12812 (10) | 0.0432 (4) | |
C12 | 0.14355 (11) | 0.6304 (3) | 0.24107 (10) | 0.0368 (3) | |
H12A | 0.1759 (14) | 0.451 (3) | 0.2702 (12) | 0.055* | |
H11A | 0.1008 (14) | 0.432 (3) | 0.1063 (12) | 0.055* | |
H11B | 0.0064 (15) | 0.666 (3) | 0.0963 (12) | 0.055* | |
H1A | 0.0164 (16) | 0.566 (4) | 0.2570 (12) | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0483 (6) | 0.0379 (5) | 0.0658 (7) | −0.0024 (4) | 0.0393 (5) | −0.0036 (5) |
C1 | 0.0346 (6) | 0.0296 (6) | 0.0496 (8) | 0.0059 (5) | 0.0243 (6) | 0.0038 (6) |
C2 | 0.0356 (7) | 0.0326 (7) | 0.0429 (7) | 0.0066 (5) | 0.0197 (6) | 0.0025 (5) |
C3 | 0.0457 (8) | 0.0464 (8) | 0.0448 (8) | 0.0060 (6) | 0.0175 (6) | −0.0018 (6) |
C4 | 0.0380 (8) | 0.0510 (9) | 0.0543 (9) | −0.0002 (6) | 0.0092 (7) | −0.0112 (7) |
C5 | 0.0369 (8) | 0.0451 (8) | 0.0802 (12) | −0.0035 (6) | 0.0256 (8) | −0.0040 (8) |
C6 | 0.0393 (7) | 0.0369 (7) | 0.0667 (9) | 0.0046 (6) | 0.0316 (7) | 0.0049 (7) |
C7 | 0.0629 (10) | 0.0483 (9) | 0.0910 (13) | 0.0014 (8) | 0.0545 (10) | 0.0139 (9) |
C8 | 0.0819 (12) | 0.0590 (10) | 0.0669 (11) | 0.0048 (9) | 0.0511 (10) | 0.0114 (9) |
C9 | 0.0684 (10) | 0.0533 (9) | 0.0449 (8) | 0.0035 (8) | 0.0325 (8) | 0.0028 (7) |
C10 | 0.0447 (8) | 0.0371 (7) | 0.0432 (7) | 0.0065 (6) | 0.0242 (6) | 0.0023 (6) |
C11 | 0.0441 (8) | 0.0398 (7) | 0.0442 (8) | −0.0034 (6) | 0.0205 (6) | −0.0040 (6) |
C12 | 0.0393 (7) | 0.0293 (7) | 0.0480 (8) | 0.0045 (5) | 0.0262 (6) | 0.0044 (6) |
Geometric parameters (Å, º) top
O1—C12 | 1.4328 (15) | C6—C7 | 1.419 (2) |
O1—H1A | 0.813 (18) | C7—C8 | 1.365 (3) |
C1—C2 | 1.3989 (19) | C7—H7 | 0.9300 |
C1—C6 | 1.4020 (19) | C8—C9 | 1.410 (2) |
C1—C10 | 1.4187 (19) | C8—H8 | 0.9300 |
C2—C3 | 1.365 (2) | C9—C10 | 1.362 (2) |
C2—C12 | 1.5107 (18) | C9—H9 | 0.9300 |
C3—C4 | 1.422 (2) | C10—C11 | 1.5070 (19) |
C3—H3 | 0.9300 | C11—C12 | 1.560 (2) |
C4—C5 | 1.362 (2) | C11—H11A | 1.002 (17) |
C4—H4 | 0.9300 | C11—H11B | 1.017 (16) |
C5—C6 | 1.426 (2) | C12—H12A | 0.988 (17) |
C5—H5 | 0.9300 | | |
| | | |
C12—O1—H1A | 104.0 (12) | C7—C8—C9 | 122.98 (15) |
C2—C1—C6 | 124.51 (13) | C7—C8—H8 | 118.5 |
C2—C1—C10 | 112.36 (12) | C9—C8—H8 | 118.5 |
C6—C1—C10 | 123.13 (13) | C10—C9—C8 | 119.09 (15) |
C3—C2—C1 | 118.59 (13) | C10—C9—H9 | 120.5 |
C3—C2—C12 | 132.09 (13) | C8—C9—H9 | 120.5 |
C1—C2—C12 | 109.32 (11) | C9—C10—C1 | 118.50 (13) |
C2—C3—C4 | 118.62 (14) | C9—C10—C11 | 133.19 (14) |
C2—C3—H3 | 120.7 | C1—C10—C11 | 108.30 (12) |
C4—C3—H3 | 120.7 | C10—C11—C12 | 105.48 (11) |
C5—C4—C3 | 122.61 (14) | C10—C11—H11A | 111.0 (9) |
C5—C4—H4 | 118.7 | C12—C11—H11A | 111.4 (9) |
C3—C4—H4 | 118.7 | C10—C11—H11B | 114.2 (9) |
C4—C5—C6 | 120.21 (14) | C12—C11—H11B | 106.7 (9) |
C4—C5—H5 | 119.9 | H11A—C11—H11B | 108.1 (13) |
C6—C5—H5 | 119.9 | O1—C12—C2 | 110.26 (10) |
C1—C6—C7 | 116.65 (14) | O1—C12—C11 | 112.78 (11) |
C1—C6—C5 | 115.46 (14) | C2—C12—C11 | 104.50 (10) |
C7—C6—C5 | 127.89 (14) | O1—C12—H12A | 108.1 (9) |
C8—C7—C6 | 119.65 (15) | C2—C12—H12A | 111.5 (10) |
C8—C7—H7 | 120.2 | C11—C12—H12A | 109.8 (9) |
C6—C7—H7 | 120.2 | | |
| | | |
C6—C1—C2—C3 | 0.31 (19) | C6—C7—C8—C9 | 0.3 (3) |
C10—C1—C2—C3 | −179.54 (11) | C7—C8—C9—C10 | 0.0 (3) |
C6—C1—C2—C12 | −179.06 (11) | C8—C9—C10—C1 | −0.3 (2) |
C10—C1—C2—C12 | 1.09 (14) | C8—C9—C10—C11 | 179.99 (15) |
C1—C2—C3—C4 | 0.15 (19) | C2—C1—C10—C9 | −179.79 (12) |
C12—C2—C3—C4 | 179.35 (13) | C6—C1—C10—C9 | 0.4 (2) |
C2—C3—C4—C5 | −0.5 (2) | C2—C1—C10—C11 | −0.01 (15) |
C3—C4—C5—C6 | 0.4 (2) | C6—C1—C10—C11 | −179.86 (12) |
C2—C1—C6—C7 | −179.93 (12) | C9—C10—C11—C12 | 178.72 (15) |
C10—C1—C6—C7 | −0.09 (19) | C1—C10—C11—C12 | −1.02 (14) |
C2—C1—C6—C5 | −0.41 (19) | C3—C2—C12—O1 | 57.64 (19) |
C10—C1—C6—C5 | 179.42 (12) | C1—C2—C12—O1 | −123.10 (11) |
C4—C5—C6—C1 | 0.0 (2) | C3—C2—C12—C11 | 179.09 (14) |
C4—C5—C6—C7 | 179.50 (14) | C1—C2—C12—C11 | −1.65 (13) |
C1—C6—C7—C8 | −0.2 (2) | C10—C11—C12—O1 | 121.36 (12) |
C5—C6—C7—C8 | −179.67 (15) | C10—C11—C12—C2 | 1.59 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O1i | 0.82 (2) | 1.97 (2) | 2.771 (1) | 170 (2) |
C11—H11A···Cg3ii | 1.00 (2) | 2.77 (2) | 3.653 (2) | 147 (1) |
C12—H12A···Cg2ii | 0.99 (2) | 2.69 (2) | 3.558 (2) | 146 (2) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, y−1, z. |
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