The title molecule, C
17H
16O
2, lies on a crystallographic twofold rotation axis. The dihedral angle between the planes of the two symmetry-related benzene rings is 15.56 (4)°. The molecular structure is stabilized by intramolecular O—H
O and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 262445
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.001 Å
- R factor = 0.039
- wR factor = 0.117
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.29 Ratio
PLAT391_ALERT_3_C Deviating Methyl C9 H-C-H Bond Angle ...... 101.90 Deg.
PLAT733_ALERT_1_C Torsion Calc -0.89(11), Rep -0.89(5) ...... 2.20 su-Rat
C2 -C1 -C2 -O1 2.655 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-Hydroxy-1,3-di-
p-tolylpropenone
top
Crystal data top
C17H16O2 | F(000) = 536 |
Mr = 252.30 | Dx = 1.286 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 17951 reflections |
a = 11.280 (5) Å | θ = 2.1–29.1° |
b = 11.884 (5) Å | µ = 0.08 mm−1 |
c = 10.657 (5) Å | T = 150 K |
β = 114.169 (5)° | Prism, colourless |
V = 1303.4 (10) Å3 | 0.40 × 0.35 × 0.31 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 1705 independent reflections |
Radiation source: fine-focus sealed tube | 1490 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.090 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.9°, θmin = 2.6° |
ω scans | h = −15→15 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −16→16 |
Tmin = 0.971, Tmax = 0.983 | l = −14→14 |
10682 measured reflections | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0703P)2 + 0.2674P] where P = (Fo2 + 2Fc2)/3 |
1705 reflections | (Δ/σ)max = 0.001 |
121 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.16 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 | Occ. (<1) |
O1 | 0.58092 (6) | 0.17965 (6) | 0.36844 (6) | 0.0297 (2) | |
H1O | 0.516 (5) | 0.194 (2) | 0.276 (5) | 0.071 (11)* | 0.50 |
C1 | 0.5000 | 0.01162 (10) | 0.2500 | 0.0246 (3) | |
H1C | 0.5000 | −0.0670 (15) | 0.2500 | 0.031 (4)* | |
C2 | 0.57919 (8) | 0.07083 (8) | 0.36826 (8) | 0.0237 (2) | |
C3 | 0.66456 (8) | 0.01498 (7) | 0.49793 (8) | 0.0239 (2) | |
C4 | 0.75176 (8) | 0.08072 (8) | 0.60492 (9) | 0.0272 (2) | |
H4C | 0.7570 (13) | 0.1585 (11) | 0.5907 (13) | 0.037 (3)* | |
C5 | 0.83333 (9) | 0.03122 (8) | 0.72766 (9) | 0.0297 (2) | |
H5C | 0.8956 (14) | 0.0816 (12) | 0.7999 (15) | 0.046 (4)* | |
C6 | 0.83084 (8) | −0.08447 (8) | 0.74815 (9) | 0.0280 (2) | |
C7 | 0.74303 (9) | −0.14918 (8) | 0.64198 (10) | 0.0300 (2) | |
H7C | 0.7396 (13) | −0.2319 (12) | 0.6569 (14) | 0.045 (4)* | |
C8 | 0.66116 (9) | −0.10049 (8) | 0.51843 (9) | 0.0279 (2) | |
H8C | 0.5993 (14) | −0.1530 (11) | 0.4473 (15) | 0.044 (3)* | |
C9 | 0.92149 (10) | −0.13762 (10) | 0.88058 (11) | 0.0370 (3) | |
H9A | 0.898 (2) | −0.1202 (17) | 0.954 (2) | 0.084 (6)* | |
H9B | 1.0105 (19) | −0.1163 (16) | 0.9046 (19) | 0.076 (5)* | |
H9C | 0.916 (2) | −0.223 (2) | 0.878 (2) | 0.102 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0359 (4) | 0.0206 (3) | 0.0270 (3) | −0.0019 (2) | 0.0070 (3) | −0.0005 (2) |
C1 | 0.0272 (5) | 0.0204 (5) | 0.0242 (5) | 0.000 | 0.0084 (4) | 0.000 |
C2 | 0.0239 (4) | 0.0228 (4) | 0.0246 (4) | −0.0004 (3) | 0.0103 (3) | 0.0007 (3) |
C3 | 0.0239 (4) | 0.0239 (4) | 0.0234 (4) | −0.0004 (3) | 0.0094 (3) | 0.0009 (3) |
C4 | 0.0278 (4) | 0.0246 (4) | 0.0267 (4) | −0.0024 (3) | 0.0086 (3) | −0.0001 (3) |
C5 | 0.0270 (4) | 0.0330 (5) | 0.0252 (4) | −0.0017 (3) | 0.0066 (3) | −0.0001 (3) |
C6 | 0.0253 (4) | 0.0338 (5) | 0.0265 (4) | 0.0046 (3) | 0.0123 (3) | 0.0056 (3) |
C7 | 0.0330 (5) | 0.0257 (4) | 0.0317 (5) | 0.0024 (3) | 0.0137 (4) | 0.0053 (3) |
C8 | 0.0301 (4) | 0.0240 (4) | 0.0271 (4) | −0.0021 (3) | 0.0093 (3) | 0.0003 (3) |
C9 | 0.0321 (5) | 0.0461 (6) | 0.0307 (5) | 0.0070 (4) | 0.0106 (4) | 0.0119 (4) |
Geometric parameters (Å, º) top
O1—C2 | 1.2934 (12) | C5—C6 | 1.3942 (14) |
O1—H1O | 0.97 (5) | C5—H5C | 1.001 (15) |
C1—C2 | 1.3998 (11) | C6—C7 | 1.3910 (14) |
C1—C2i | 1.3998 (11) | C6—C9 | 1.5015 (13) |
C1—H1C | 0.934 (18) | C7—C8 | 1.3876 (13) |
C2—C3 | 1.4791 (12) | C7—H7C | 0.999 (14) |
C3—C8 | 1.3925 (13) | C8—H8C | 1.009 (14) |
C3—C4 | 1.3999 (12) | C9—H9A | 0.94 (2) |
C4—C5 | 1.3849 (13) | C9—H9B | 0.963 (19) |
C4—H4C | 0.942 (13) | C9—H9C | 1.02 (2) |
| | | |
C2—O1—H1O | 99.6 (17) | C7—C6—C5 | 118.11 (8) |
C2—C1—C2i | 119.65 (11) | C7—C6—C9 | 121.07 (9) |
C2—C1—H1C | 120.18 (6) | C5—C6—C9 | 120.82 (9) |
C2i—C1—H1C | 120.18 (6) | C8—C7—C6 | 121.12 (9) |
O1—C2—C1 | 120.51 (8) | C8—C7—H7C | 120.5 (8) |
O1—C2—C3 | 116.33 (7) | C6—C7—H7C | 118.4 (8) |
C1—C2—C3 | 123.16 (9) | C7—C8—C3 | 120.62 (8) |
C8—C3—C4 | 118.52 (8) | C7—C8—H8C | 116.2 (8) |
C8—C3—C2 | 122.65 (8) | C3—C8—H8C | 123.1 (8) |
C4—C3—C2 | 118.83 (8) | C6—C9—H9A | 111.8 (12) |
C5—C4—C3 | 120.39 (9) | C6—C9—H9B | 112.0 (11) |
C5—C4—H4C | 120.5 (8) | H9A—C9—H9B | 109.7 (16) |
C3—C4—H4C | 119.1 (8) | C6—C9—H9C | 112.8 (13) |
C4—C5—C6 | 121.23 (8) | H9A—C9—H9C | 101.8 (17) |
C4—C5—H5C | 117.2 (8) | H9B—C9—H9C | 108.3 (16) |
C6—C5—H5C | 121.5 (8) | | |
| | | |
C2i—C1—C2—O1 | −0.89 (5) | C3—C4—C5—C6 | −0.12 (14) |
C2i—C1—C2—C3 | 179.28 (8) | C4—C5—C6—C7 | −0.54 (13) |
O1—C2—C3—C8 | 171.94 (8) | C4—C5—C6—C9 | 178.79 (8) |
C1—C2—C3—C8 | −8.22 (12) | C5—C6—C7—C8 | 0.75 (13) |
O1—C2—C3—C4 | −7.60 (11) | C9—C6—C7—C8 | −178.59 (8) |
C1—C2—C3—C4 | 172.24 (7) | C6—C7—C8—C3 | −0.30 (14) |
C8—C3—C4—C5 | 0.57 (13) | C4—C3—C8—C7 | −0.37 (13) |
C2—C3—C4—C5 | −179.87 (8) | C2—C3—C8—C7 | −179.91 (8) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1i | 0.97 (5) | 1.49 (5) | 2.436 (1) | 163 (2) |
C4—H4C···O1 | 0.94 (1) | 2.40 (1) | 2.733 (1) | 100 (1) |
C4—H4C···O1ii | 0.94 (1) | 2.57 (1) | 3.364 (2) | 143 (1) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+3/2, −y+1/2, −z+1. |