Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026517/xu2265sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026517/xu2265Isup2.hkl |
CCDC reference: 654959
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.103
- Data-to-parameter ratio = 8.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1 ... ?
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.10 From the CIF: _reflns_number_total 2536 Count of symmetry unique reflns 2577 Completeness (_total/calc) 98.41% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT792_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT792_ALERT_1_G Check the Absolute Configuration of C21 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Mixing 5.2 g styrene (0.05 mol) in 100 ml toluene with 11 g (0.1 mol) m-dihydroxybenzene and 1 g H2SO4 (0.01 mol) and refluxing the mixture for 6 h to give 8.6 g 4-(1-Phenylethyl)benzene-1,3-diol crystals after distilling and cooling the mixture to room temperature.
H atoms bonded to O atoms were located in a difference map and refined with distance restraints of O—H = 0.82 Å, and with Uiso(H) = 1.5Ueq(O). Other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and with Uiso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C) for others. In the absence of significant anomalous dispersion effects, Friedel pairs were merged.
4-(1-Phenylethyl)benzene-1,3-diol is a polyphenol, which exhibits potential free radical scavenging property applied to food as antioxidant and potential tyrosinase inhibitory property applied to cosmetics as skin brightener (Buu-Hoi, et al., 1952). We here report its crystal structure.
The X-ray study of the title compound confirms the previously proposed molecular structure based on spectroscopic data. There are two crystallographically independent molecules in the asymmetric unit (Fig. 1). Intermolecular O—H···O hydrogen bonding between hydroxy groups occurs in the crystal (Table 1), resulting in the supra-molecular structure (Fig. 2).
For general background, see: Buu-Hoi et al. (1952).
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C14H14O2 | F(000) = 912 |
Mr = 214.25 | Dx = 1.247 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 984 reflections |
a = 13.131 (4) Å | θ = 2.7–23.9° |
b = 5.7841 (15) Å | µ = 0.08 mm−1 |
c = 30.046 (8) Å | T = 293 K |
V = 2282.0 (10) Å3 | Block, colourless |
Z = 8 | 0.47 × 0.41 × 0.36 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 1675 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.1°, θmin = 3.1° |
φ and ω scans | h = −16→16 |
10800 measured reflections | k = −7→5 |
2536 independent reflections | l = −38→36 |
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) = 0.103 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0514P)2 + 0.0955P] where P = (Fo2 + 2Fc2)/3 |
2536 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 0.12 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
C14H14O2 | V = 2282.0 (10) Å3 |
Mr = 214.25 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 13.131 (4) Å | µ = 0.08 mm−1 |
b = 5.7841 (15) Å | T = 293 K |
c = 30.046 (8) Å | 0.47 × 0.41 × 0.36 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 1675 reflections with I > 2σ(I) |
10800 measured reflections | Rint = 0.035 |
2536 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.12 e Å−3 |
2536 reflections | Δρmin = −0.14 e Å−3 |
293 parameters |
Experimental. The compound identity was conformed by the 1H NMR spectra and ESI-MS. 1H NMR (300 MHz, DMSO-d6): δ 9.11(br, 1H, –OH), 8.98(br, 1H, –OH), 7.20–7.15 (5H, aromatic),7.10 (1H, aromatic), 6.82 (1H, aromatic), 6.22 (1H, aromatic), 6.14 (1H, aromatic) 4.30 (q, 1H), 1.44 (d, 3H). ESI-MS (m/z): 213[M]-. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3184 (2) | 0.1413 (5) | 0.40687 (9) | 0.0505 (7) | |
C2 | 0.3112 (2) | 0.3209 (6) | 0.37688 (10) | 0.0524 (7) | |
H2A | 0.3673 | 0.3616 | 0.3597 | 0.063* | |
C3 | 0.2211 (2) | 0.4400 (6) | 0.37243 (10) | 0.0489 (7) | |
C4 | 0.1393 (2) | 0.3845 (6) | 0.39909 (11) | 0.0564 (8) | |
H4A | 0.0786 | 0.4664 | 0.3969 | 0.068* | |
C5 | 0.1493 (2) | 0.2054 (6) | 0.42905 (10) | 0.0570 (8) | |
H5A | 0.0938 | 0.1698 | 0.4470 | 0.068* | |
C6 | 0.2371 (2) | 0.0756 (5) | 0.43391 (9) | 0.0477 (7) | |
C7 | 0.2454 (3) | −0.1395 (5) | 0.46271 (10) | 0.0544 (8) | |
H7A | 0.2615 | −0.2680 | 0.4426 | 0.065* | |
C8 | 0.1456 (3) | −0.2039 (7) | 0.48646 (13) | 0.0777 (11) | |
H8A | 0.1560 | −0.3404 | 0.5040 | 0.117* | |
H8B | 0.0935 | −0.2326 | 0.4647 | 0.117* | |
H8C | 0.1250 | −0.0788 | 0.5054 | 0.117* | |
C9 | 0.3289 (2) | −0.1328 (5) | 0.49728 (10) | 0.0506 (7) | |
C10 | 0.3943 (3) | −0.3191 (6) | 0.50251 (12) | 0.0711 (10) | |
H10A | 0.3902 | −0.4432 | 0.4829 | 0.085* | |
C11 | 0.4648 (3) | −0.3232 (7) | 0.53610 (14) | 0.0801 (11) | |
H11A | 0.5069 | −0.4514 | 0.5394 | 0.096* | |
C12 | 0.4742 (3) | −0.1426 (7) | 0.56472 (12) | 0.0744 (10) | |
H12A | 0.5221 | −0.1470 | 0.5875 | 0.089* | |
C13 | 0.4121 (3) | 0.0462 (7) | 0.55966 (13) | 0.0716 (10) | |
H13A | 0.4186 | 0.1718 | 0.5788 | 0.086* | |
C14 | 0.3395 (3) | 0.0502 (6) | 0.52595 (12) | 0.0617 (9) | |
H14A | 0.2975 | 0.1787 | 0.5228 | 0.074* | |
O1 | 0.40876 (18) | 0.0228 (5) | 0.40921 (8) | 0.0709 (7) | |
H1 | 0.4109 | −0.0510 | 0.4325 | 0.106* | |
O2 | 0.21656 (15) | 0.6154 (4) | 0.34190 (8) | 0.0638 (6) | |
H2 | 0.1634 | 0.6879 | 0.3453 | 0.096* | |
C15 | 0.4370 (2) | 0.6411 (6) | 0.27380 (9) | 0.0532 (8) | |
C16 | 0.4458 (2) | 0.8177 (6) | 0.30385 (9) | 0.0533 (8) | |
H16A | 0.3904 | 0.8601 | 0.3213 | 0.064* | |
C17 | 0.5374 (2) | 0.9326 (6) | 0.30808 (10) | 0.0505 (7) | |
C18 | 0.6188 (2) | 0.8732 (6) | 0.28212 (11) | 0.0552 (8) | |
H18A | 0.6804 | 0.9513 | 0.2848 | 0.066* | |
C19 | 0.6079 (2) | 0.6948 (6) | 0.25181 (11) | 0.0568 (8) | |
H19A | 0.6630 | 0.6568 | 0.2338 | 0.068* | |
C20 | 0.5186 (2) | 0.5709 (5) | 0.24720 (9) | 0.0490 (7) | |
C21 | 0.5059 (2) | 0.3644 (5) | 0.21609 (11) | 0.0570 (8) | |
H21A | 0.4821 | 0.2352 | 0.2344 | 0.068* | |
C22 | 0.6056 (3) | 0.2857 (7) | 0.19424 (13) | 0.0758 (10) | |
H22A | 0.6558 | 0.2579 | 0.2168 | 0.114* | |
H22B | 0.6295 | 0.4041 | 0.1744 | 0.114* | |
H22C | 0.5939 | 0.1460 | 0.1778 | 0.114* | |
C23 | 0.4250 (2) | 0.4040 (5) | 0.18056 (11) | 0.0517 (8) | |
C24 | 0.4247 (3) | 0.6009 (6) | 0.15445 (11) | 0.0609 (8) | |
H24A | 0.4724 | 0.7165 | 0.1598 | 0.073* | |
C25 | 0.3549 (3) | 0.6287 (7) | 0.12061 (12) | 0.0709 (9) | |
H25A | 0.3559 | 0.7627 | 0.1035 | 0.085* | |
C26 | 0.2847 (3) | 0.4624 (7) | 0.11196 (13) | 0.0740 (10) | |
H26A | 0.2378 | 0.4819 | 0.0890 | 0.089* | |
C27 | 0.2834 (3) | 0.2660 (7) | 0.13724 (14) | 0.0759 (10) | |
H27A | 0.2356 | 0.1513 | 0.1314 | 0.091* | |
C28 | 0.3524 (3) | 0.2367 (6) | 0.17134 (12) | 0.0650 (9) | |
H28A | 0.3503 | 0.1026 | 0.1884 | 0.078* | |
O3 | 0.34586 (18) | 0.5241 (5) | 0.27004 (9) | 0.0731 (7) | |
H3 | 0.3095 | 0.5549 | 0.2914 | 0.110* | |
O4 | 0.54612 (17) | 1.1101 (4) | 0.33921 (8) | 0.0672 (6) | |
H4 | 0.5120 | 1.0786 | 0.3612 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0398 (16) | 0.0738 (19) | 0.0378 (16) | 0.0007 (14) | 0.0008 (12) | −0.0042 (15) |
C2 | 0.0360 (15) | 0.079 (2) | 0.0419 (15) | 0.0021 (14) | 0.0078 (12) | 0.0001 (16) |
C3 | 0.0410 (17) | 0.0643 (19) | 0.0413 (17) | 0.0004 (14) | 0.0024 (14) | −0.0099 (15) |
C4 | 0.0353 (16) | 0.076 (2) | 0.0575 (19) | 0.0010 (15) | 0.0050 (14) | −0.0120 (18) |
C5 | 0.0408 (17) | 0.077 (2) | 0.0534 (18) | −0.0125 (15) | 0.0118 (14) | −0.0090 (17) |
C6 | 0.0414 (16) | 0.0636 (17) | 0.0381 (16) | −0.0067 (15) | 0.0056 (13) | −0.0104 (14) |
C7 | 0.0554 (18) | 0.0586 (18) | 0.0492 (18) | −0.0098 (15) | 0.0112 (14) | −0.0140 (14) |
C8 | 0.068 (2) | 0.090 (3) | 0.076 (2) | −0.0267 (19) | 0.0135 (19) | 0.005 (2) |
C9 | 0.0533 (18) | 0.0514 (17) | 0.0471 (18) | −0.0020 (14) | 0.0142 (14) | −0.0005 (14) |
C10 | 0.086 (3) | 0.059 (2) | 0.068 (2) | 0.0082 (19) | 0.019 (2) | 0.0012 (17) |
C11 | 0.079 (3) | 0.076 (2) | 0.085 (3) | 0.023 (2) | 0.011 (2) | 0.020 (2) |
C12 | 0.057 (2) | 0.100 (3) | 0.066 (2) | 0.005 (2) | −0.0010 (18) | 0.022 (2) |
C13 | 0.070 (2) | 0.081 (3) | 0.064 (2) | 0.003 (2) | −0.0053 (19) | −0.0122 (19) |
C14 | 0.063 (2) | 0.062 (2) | 0.060 (2) | 0.0120 (16) | 0.0007 (17) | −0.0068 (17) |
O1 | 0.0482 (14) | 0.1065 (19) | 0.0579 (18) | 0.0221 (12) | 0.0097 (12) | 0.0169 (13) |
O2 | 0.0518 (14) | 0.0757 (15) | 0.0637 (15) | 0.0183 (11) | 0.0078 (11) | 0.0049 (12) |
C15 | 0.0384 (16) | 0.082 (2) | 0.0394 (16) | −0.0084 (14) | 0.0028 (12) | 0.0044 (15) |
C16 | 0.0396 (17) | 0.079 (2) | 0.0412 (16) | −0.0064 (14) | 0.0066 (13) | −0.0025 (16) |
C17 | 0.0455 (18) | 0.065 (2) | 0.0413 (17) | −0.0060 (15) | −0.0003 (14) | 0.0051 (15) |
C18 | 0.0360 (16) | 0.071 (2) | 0.0588 (19) | −0.0060 (15) | 0.0036 (14) | 0.0058 (17) |
C19 | 0.0405 (17) | 0.071 (2) | 0.0585 (19) | 0.0054 (15) | 0.0110 (14) | 0.0090 (17) |
C20 | 0.0410 (17) | 0.0626 (19) | 0.0435 (17) | 0.0050 (15) | 0.0035 (13) | 0.0066 (14) |
C21 | 0.0609 (19) | 0.0572 (18) | 0.0530 (19) | 0.0029 (16) | 0.0110 (17) | 0.0069 (15) |
C22 | 0.068 (2) | 0.081 (2) | 0.078 (2) | 0.0172 (18) | 0.0145 (19) | −0.004 (2) |
C23 | 0.0540 (19) | 0.0550 (18) | 0.0461 (17) | 0.0007 (15) | 0.0126 (14) | −0.0056 (14) |
C24 | 0.068 (2) | 0.0565 (19) | 0.058 (2) | −0.0060 (16) | −0.0018 (17) | 0.0010 (16) |
C25 | 0.084 (3) | 0.071 (2) | 0.058 (2) | 0.008 (2) | −0.0048 (19) | −0.0001 (18) |
C26 | 0.063 (2) | 0.090 (3) | 0.069 (2) | 0.008 (2) | −0.0070 (19) | −0.018 (2) |
C27 | 0.059 (2) | 0.082 (3) | 0.086 (3) | −0.0068 (19) | −0.001 (2) | −0.020 (2) |
C28 | 0.064 (2) | 0.0587 (19) | 0.072 (2) | −0.0054 (16) | 0.0144 (18) | −0.0040 (17) |
O3 | 0.0437 (13) | 0.119 (2) | 0.0565 (16) | −0.0240 (13) | 0.0128 (12) | −0.0153 (13) |
O4 | 0.0624 (14) | 0.0819 (16) | 0.0573 (15) | −0.0196 (12) | 0.0141 (11) | −0.0042 (12) |
C1—O1 | 1.372 (4) | C15—C16 | 1.369 (4) |
C1—C2 | 1.378 (4) | C15—O3 | 1.379 (4) |
C1—C6 | 1.395 (4) | C15—C20 | 1.398 (4) |
C2—C3 | 1.375 (4) | C16—C17 | 1.381 (4) |
C2—H2A | 0.9300 | C16—H16A | 0.9300 |
C3—O2 | 1.369 (4) | C17—C18 | 1.367 (4) |
C3—C4 | 1.378 (4) | C17—O4 | 1.393 (4) |
C4—C5 | 1.379 (5) | C18—C19 | 1.384 (5) |
C4—H4A | 0.9300 | C18—H18A | 0.9300 |
C5—C6 | 1.384 (4) | C19—C20 | 1.381 (5) |
C5—H5A | 0.9300 | C19—H19A | 0.9300 |
C6—C7 | 1.519 (4) | C20—C21 | 1.526 (4) |
C7—C9 | 1.510 (5) | C21—C23 | 1.523 (5) |
C7—C8 | 1.538 (5) | C21—C22 | 1.534 (5) |
C7—H7A | 0.9800 | C21—H21A | 0.9800 |
C8—H8A | 0.9600 | C22—H22A | 0.9600 |
C8—H8B | 0.9600 | C22—H22B | 0.9600 |
C8—H8C | 0.9600 | C22—H22C | 0.9600 |
C9—C14 | 1.372 (5) | C23—C24 | 1.383 (4) |
C9—C10 | 1.387 (5) | C23—C28 | 1.386 (5) |
C10—C11 | 1.370 (6) | C24—C25 | 1.378 (5) |
C10—H10A | 0.9300 | C24—H24A | 0.9300 |
C11—C12 | 1.358 (5) | C25—C26 | 1.358 (5) |
C11—H11A | 0.9300 | C25—H25A | 0.9300 |
C12—C13 | 1.371 (5) | C26—C27 | 1.367 (5) |
C12—H12A | 0.9300 | C26—H26A | 0.9300 |
C13—C14 | 1.391 (5) | C27—C28 | 1.379 (5) |
C13—H13A | 0.9300 | C27—H27A | 0.9300 |
C14—H14A | 0.9300 | C28—H28A | 0.9300 |
O1—H1 | 0.8200 | O3—H3 | 0.8200 |
O2—H2 | 0.8200 | O4—H4 | 0.8200 |
O1—C1—C2 | 118.0 (3) | C16—C15—O3 | 119.6 (3) |
O1—C1—C6 | 119.7 (3) | C16—C15—C20 | 122.0 (3) |
C2—C1—C6 | 122.3 (3) | O3—C15—C20 | 118.4 (3) |
C3—C2—C1 | 120.0 (3) | C15—C16—C17 | 119.6 (3) |
C3—C2—H2A | 120.0 | C15—C16—H16A | 120.2 |
C1—C2—H2A | 120.0 | C17—C16—H16A | 120.2 |
O2—C3—C2 | 118.3 (3) | C18—C17—C16 | 120.5 (3) |
O2—C3—C4 | 121.9 (3) | C18—C17—O4 | 120.3 (3) |
C2—C3—C4 | 119.8 (3) | C16—C17—O4 | 119.2 (3) |
C3—C4—C5 | 118.7 (3) | C17—C18—C19 | 118.8 (3) |
C3—C4—H4A | 120.6 | C17—C18—H18A | 120.6 |
C5—C4—H4A | 120.6 | C19—C18—H18A | 120.6 |
C4—C5—C6 | 123.8 (3) | C20—C19—C18 | 122.8 (3) |
C4—C5—H5A | 118.1 | C20—C19—H19A | 118.6 |
C6—C5—H5A | 118.1 | C18—C19—H19A | 118.6 |
C5—C6—C1 | 115.4 (3) | C19—C20—C15 | 116.3 (3) |
C5—C6—C7 | 124.4 (3) | C19—C20—C21 | 124.1 (3) |
C1—C6—C7 | 120.0 (3) | C15—C20—C21 | 119.6 (3) |
C9—C7—C6 | 115.0 (3) | C23—C21—C20 | 112.9 (2) |
C9—C7—C8 | 107.8 (3) | C23—C21—C22 | 109.9 (3) |
C6—C7—C8 | 113.6 (3) | C20—C21—C22 | 113.6 (3) |
C9—C7—H7A | 106.6 | C23—C21—H21A | 106.7 |
C6—C7—H7A | 106.6 | C20—C21—H21A | 106.7 |
C8—C7—H7A | 106.6 | C22—C21—H21A | 106.7 |
C7—C8—H8A | 109.5 | C21—C22—H22A | 109.5 |
C7—C8—H8B | 109.5 | C21—C22—H22B | 109.5 |
H8A—C8—H8B | 109.5 | H22A—C22—H22B | 109.5 |
C7—C8—H8C | 109.5 | C21—C22—H22C | 109.5 |
H8A—C8—H8C | 109.5 | H22A—C22—H22C | 109.5 |
H8B—C8—H8C | 109.5 | H22B—C22—H22C | 109.5 |
C14—C9—C10 | 117.8 (3) | C24—C23—C28 | 117.3 (3) |
C14—C9—C7 | 121.7 (3) | C24—C23—C21 | 121.6 (3) |
C10—C9—C7 | 120.5 (3) | C28—C23—C21 | 121.0 (3) |
C11—C10—C9 | 121.0 (4) | C25—C24—C23 | 121.1 (3) |
C11—C10—H10A | 119.5 | C25—C24—H24A | 119.4 |
C9—C10—H10A | 119.5 | C23—C24—H24A | 119.4 |
C12—C11—C10 | 120.9 (3) | C26—C25—C24 | 120.7 (3) |
C12—C11—H11A | 119.5 | C26—C25—H25A | 119.7 |
C10—C11—H11A | 119.5 | C24—C25—H25A | 119.7 |
C11—C12—C13 | 119.2 (4) | C25—C26—C27 | 119.4 (4) |
C11—C12—H12A | 120.4 | C25—C26—H26A | 120.3 |
C13—C12—H12A | 120.4 | C27—C26—H26A | 120.3 |
C12—C13—C14 | 120.1 (4) | C26—C27—C28 | 120.5 (3) |
C12—C13—H13A | 119.9 | C26—C27—H27A | 119.8 |
C14—C13—H13A | 119.9 | C28—C27—H27A | 119.8 |
C9—C14—C13 | 120.9 (3) | C27—C28—C23 | 121.0 (3) |
C9—C14—H14A | 119.5 | C27—C28—H28A | 119.5 |
C13—C14—H14A | 119.5 | C23—C28—H28A | 119.5 |
C1—O1—H1 | 109.5 | C15—O3—H3 | 109.5 |
C3—O2—H2 | 109.5 | C17—O4—H4 | 109.5 |
O1—C1—C2—C3 | 178.0 (3) | O3—C15—C16—C17 | 179.1 (3) |
C6—C1—C2—C3 | −0.9 (4) | C20—C15—C16—C17 | 0.6 (5) |
C1—C2—C3—O2 | −179.2 (3) | C15—C16—C17—C18 | 0.8 (5) |
C1—C2—C3—C4 | 2.3 (4) | C15—C16—C17—O4 | −179.1 (3) |
O2—C3—C4—C5 | 179.9 (3) | C16—C17—C18—C19 | −0.5 (5) |
C2—C3—C4—C5 | −1.6 (5) | O4—C17—C18—C19 | 179.4 (3) |
C3—C4—C5—C6 | −0.4 (5) | C17—C18—C19—C20 | −1.2 (5) |
C4—C5—C6—C1 | 1.6 (4) | C18—C19—C20—C15 | 2.5 (5) |
C4—C5—C6—C7 | −172.5 (3) | C18—C19—C20—C21 | −176.3 (3) |
O1—C1—C6—C5 | −179.9 (3) | C16—C15—C20—C19 | −2.2 (4) |
C2—C1—C6—C5 | −1.0 (4) | O3—C15—C20—C19 | 179.3 (3) |
O1—C1—C6—C7 | −5.5 (4) | C16—C15—C20—C21 | 176.7 (3) |
C2—C1—C6—C7 | 173.4 (3) | O3—C15—C20—C21 | −1.8 (4) |
C5—C6—C7—C9 | −124.6 (3) | C19—C20—C21—C23 | −118.7 (3) |
C1—C6—C7—C9 | 61.6 (4) | C15—C20—C21—C23 | 62.6 (4) |
C5—C6—C7—C8 | 0.4 (4) | C19—C20—C21—C22 | 7.3 (4) |
C1—C6—C7—C8 | −173.5 (3) | C15—C20—C21—C22 | −171.5 (3) |
C6—C7—C9—C14 | 50.6 (4) | C20—C21—C23—C24 | 50.4 (4) |
C8—C7—C9—C14 | −77.3 (4) | C22—C21—C23—C24 | −77.5 (4) |
C6—C7—C9—C10 | −132.8 (3) | C20—C21—C23—C28 | −133.5 (3) |
C8—C7—C9—C10 | 99.3 (3) | C22—C21—C23—C28 | 98.5 (3) |
C14—C9—C10—C11 | 2.1 (5) | C28—C23—C24—C25 | −0.1 (5) |
C7—C9—C10—C11 | −174.6 (3) | C21—C23—C24—C25 | 176.1 (3) |
C9—C10—C11—C12 | −1.4 (6) | C23—C24—C25—C26 | −0.2 (5) |
C10—C11—C12—C13 | −0.2 (6) | C24—C25—C26—C27 | 0.1 (5) |
C11—C12—C13—C14 | 1.0 (5) | C25—C26—C27—C28 | 0.2 (5) |
C10—C9—C14—C13 | −1.3 (5) | C26—C27—C28—C23 | −0.5 (5) |
C7—C9—C14—C13 | 175.3 (3) | C24—C23—C28—C27 | 0.4 (5) |
C12—C13—C14—C9 | −0.2 (5) | C21—C23—C28—C27 | −175.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4i | 0.82 | 1.94 | 2.745 (3) | 166 |
O3—H3···O2 | 0.82 | 1.98 | 2.797 (3) | 177 |
O4—H4···O1ii | 0.82 | 2.00 | 2.816 (3) | 170 |
Symmetry codes: (i) x−1/2, −y+2, z; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C14H14O2 |
Mr | 214.25 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 293 |
a, b, c (Å) | 13.131 (4), 5.7841 (15), 30.046 (8) |
V (Å3) | 2282.0 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.47 × 0.41 × 0.36 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10800, 2536, 1675 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.103, 1.03 |
No. of reflections | 2536 |
No. of parameters | 293 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4i | 0.82 | 1.94 | 2.745 (3) | 166 |
O3—H3···O2 | 0.82 | 1.98 | 2.797 (3) | 177 |
O4—H4···O1ii | 0.82 | 2.00 | 2.816 (3) | 170 |
Symmetry codes: (i) x−1/2, −y+2, z; (ii) x, y+1, z. |
4-(1-Phenylethyl)benzene-1,3-diol is a polyphenol, which exhibits potential free radical scavenging property applied to food as antioxidant and potential tyrosinase inhibitory property applied to cosmetics as skin brightener (Buu-Hoi, et al., 1952). We here report its crystal structure.
The X-ray study of the title compound confirms the previously proposed molecular structure based on spectroscopic data. There are two crystallographically independent molecules in the asymmetric unit (Fig. 1). Intermolecular O—H···O hydrogen bonding between hydroxy groups occurs in the crystal (Table 1), resulting in the supra-molecular structure (Fig. 2).