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There are two crystallographically independent mol­ecules of the title compound, C14H14O2, in the asymmetric unit. Inter­molecular O—H...O hydrogen bonding between hydr­oxy groups occurs in the crystal structure, resulting in a supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026517/xu2265sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026517/xu2265Isup2.hkl
Contains datablock I

CCDC reference: 654959

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.039
  • wR factor = 0.103
  • Data-to-parameter ratio = 8.7

checkCIF/PLATON results

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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

Comment top

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).

Related literature top

For general background, see: Buu-Hoi et al. (1952).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the c axis, showing one layer of molecules connected by O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted.
4-(1-Phenylethyl)benzene-1,3-diol top
Crystal data top
C14H14O2F(000) = 912
Mr = 214.25Dx = 1.247 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 984 reflections
a = 13.131 (4) Åθ = 2.7–23.9°
b = 5.7841 (15) ŵ = 0.08 mm1
c = 30.046 (8) ÅT = 293 K
V = 2282.0 (10) Å3Block, colourless
Z = 80.47 × 0.41 × 0.36 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.1°, θmin = 3.1°
φ and ω scansh = 1616
10800 measured reflectionsk = 75
2536 independent reflectionsl = 3836
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-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 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.14 e Å3
Crystal data top
C14H14O2V = 2282.0 (10) Å3
Mr = 214.25Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 13.131 (4) ŵ = 0.08 mm1
b = 5.7841 (15) ÅT = 293 K
c = 30.046 (8) Å0.47 × 0.41 × 0.36 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1675 reflections with I > 2σ(I)
10800 measured reflectionsRint = 0.035
2536 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.103H-atom parameters constrained
S = 1.03Δρmax = 0.12 e Å3
2536 reflectionsΔρmin = 0.14 e Å3
293 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3184 (2)0.1413 (5)0.40687 (9)0.0505 (7)
C20.3112 (2)0.3209 (6)0.37688 (10)0.0524 (7)
H2A0.36730.36160.35970.063*
C30.2211 (2)0.4400 (6)0.37243 (10)0.0489 (7)
C40.1393 (2)0.3845 (6)0.39909 (11)0.0564 (8)
H4A0.07860.46640.39690.068*
C50.1493 (2)0.2054 (6)0.42905 (10)0.0570 (8)
H5A0.09380.16980.44700.068*
C60.2371 (2)0.0756 (5)0.43391 (9)0.0477 (7)
C70.2454 (3)0.1395 (5)0.46271 (10)0.0544 (8)
H7A0.26150.26800.44260.065*
C80.1456 (3)0.2039 (7)0.48646 (13)0.0777 (11)
H8A0.15600.34040.50400.117*
H8B0.09350.23260.46470.117*
H8C0.12500.07880.50540.117*
C90.3289 (2)0.1328 (5)0.49728 (10)0.0506 (7)
C100.3943 (3)0.3191 (6)0.50251 (12)0.0711 (10)
H10A0.39020.44320.48290.085*
C110.4648 (3)0.3232 (7)0.53610 (14)0.0801 (11)
H11A0.50690.45140.53940.096*
C120.4742 (3)0.1426 (7)0.56472 (12)0.0744 (10)
H12A0.52210.14700.58750.089*
C130.4121 (3)0.0462 (7)0.55966 (13)0.0716 (10)
H13A0.41860.17180.57880.086*
C140.3395 (3)0.0502 (6)0.52595 (12)0.0617 (9)
H14A0.29750.17870.52280.074*
O10.40876 (18)0.0228 (5)0.40921 (8)0.0709 (7)
H10.41090.05100.43250.106*
O20.21656 (15)0.6154 (4)0.34190 (8)0.0638 (6)
H20.16340.68790.34530.096*
C150.4370 (2)0.6411 (6)0.27380 (9)0.0532 (8)
C160.4458 (2)0.8177 (6)0.30385 (9)0.0533 (8)
H16A0.39040.86010.32130.064*
C170.5374 (2)0.9326 (6)0.30808 (10)0.0505 (7)
C180.6188 (2)0.8732 (6)0.28212 (11)0.0552 (8)
H18A0.68040.95130.28480.066*
C190.6079 (2)0.6948 (6)0.25181 (11)0.0568 (8)
H19A0.66300.65680.23380.068*
C200.5186 (2)0.5709 (5)0.24720 (9)0.0490 (7)
C210.5059 (2)0.3644 (5)0.21609 (11)0.0570 (8)
H21A0.48210.23520.23440.068*
C220.6056 (3)0.2857 (7)0.19424 (13)0.0758 (10)
H22A0.65580.25790.21680.114*
H22B0.62950.40410.17440.114*
H22C0.59390.14600.17780.114*
C230.4250 (2)0.4040 (5)0.18056 (11)0.0517 (8)
C240.4247 (3)0.6009 (6)0.15445 (11)0.0609 (8)
H24A0.47240.71650.15980.073*
C250.3549 (3)0.6287 (7)0.12061 (12)0.0709 (9)
H25A0.35590.76270.10350.085*
C260.2847 (3)0.4624 (7)0.11196 (13)0.0740 (10)
H26A0.23780.48190.08900.089*
C270.2834 (3)0.2660 (7)0.13724 (14)0.0759 (10)
H27A0.23560.15130.13140.091*
C280.3524 (3)0.2367 (6)0.17134 (12)0.0650 (9)
H28A0.35030.10260.18840.078*
O30.34586 (18)0.5241 (5)0.27004 (9)0.0731 (7)
H30.30950.55490.29140.110*
O40.54612 (17)1.1101 (4)0.33921 (8)0.0672 (6)
H40.51201.07860.36120.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0398 (16)0.0738 (19)0.0378 (16)0.0007 (14)0.0008 (12)0.0042 (15)
C20.0360 (15)0.079 (2)0.0419 (15)0.0021 (14)0.0078 (12)0.0001 (16)
C30.0410 (17)0.0643 (19)0.0413 (17)0.0004 (14)0.0024 (14)0.0099 (15)
C40.0353 (16)0.076 (2)0.0575 (19)0.0010 (15)0.0050 (14)0.0120 (18)
C50.0408 (17)0.077 (2)0.0534 (18)0.0125 (15)0.0118 (14)0.0090 (17)
C60.0414 (16)0.0636 (17)0.0381 (16)0.0067 (15)0.0056 (13)0.0104 (14)
C70.0554 (18)0.0586 (18)0.0492 (18)0.0098 (15)0.0112 (14)0.0140 (14)
C80.068 (2)0.090 (3)0.076 (2)0.0267 (19)0.0135 (19)0.005 (2)
C90.0533 (18)0.0514 (17)0.0471 (18)0.0020 (14)0.0142 (14)0.0005 (14)
C100.086 (3)0.059 (2)0.068 (2)0.0082 (19)0.019 (2)0.0012 (17)
C110.079 (3)0.076 (2)0.085 (3)0.023 (2)0.011 (2)0.020 (2)
C120.057 (2)0.100 (3)0.066 (2)0.005 (2)0.0010 (18)0.022 (2)
C130.070 (2)0.081 (3)0.064 (2)0.003 (2)0.0053 (19)0.0122 (19)
C140.063 (2)0.062 (2)0.060 (2)0.0120 (16)0.0007 (17)0.0068 (17)
O10.0482 (14)0.1065 (19)0.0579 (18)0.0221 (12)0.0097 (12)0.0169 (13)
O20.0518 (14)0.0757 (15)0.0637 (15)0.0183 (11)0.0078 (11)0.0049 (12)
C150.0384 (16)0.082 (2)0.0394 (16)0.0084 (14)0.0028 (12)0.0044 (15)
C160.0396 (17)0.079 (2)0.0412 (16)0.0064 (14)0.0066 (13)0.0025 (16)
C170.0455 (18)0.065 (2)0.0413 (17)0.0060 (15)0.0003 (14)0.0051 (15)
C180.0360 (16)0.071 (2)0.0588 (19)0.0060 (15)0.0036 (14)0.0058 (17)
C190.0405 (17)0.071 (2)0.0585 (19)0.0054 (15)0.0110 (14)0.0090 (17)
C200.0410 (17)0.0626 (19)0.0435 (17)0.0050 (15)0.0035 (13)0.0066 (14)
C210.0609 (19)0.0572 (18)0.0530 (19)0.0029 (16)0.0110 (17)0.0069 (15)
C220.068 (2)0.081 (2)0.078 (2)0.0172 (18)0.0145 (19)0.004 (2)
C230.0540 (19)0.0550 (18)0.0461 (17)0.0007 (15)0.0126 (14)0.0056 (14)
C240.068 (2)0.0565 (19)0.058 (2)0.0060 (16)0.0018 (17)0.0010 (16)
C250.084 (3)0.071 (2)0.058 (2)0.008 (2)0.0048 (19)0.0001 (18)
C260.063 (2)0.090 (3)0.069 (2)0.008 (2)0.0070 (19)0.018 (2)
C270.059 (2)0.082 (3)0.086 (3)0.0068 (19)0.001 (2)0.020 (2)
C280.064 (2)0.0587 (19)0.072 (2)0.0054 (16)0.0144 (18)0.0040 (17)
O30.0437 (13)0.119 (2)0.0565 (16)0.0240 (13)0.0128 (12)0.0153 (13)
O40.0624 (14)0.0819 (16)0.0573 (15)0.0196 (12)0.0141 (11)0.0042 (12)
Geometric parameters (Å, º) top
C1—O11.372 (4)C15—C161.369 (4)
C1—C21.378 (4)C15—O31.379 (4)
C1—C61.395 (4)C15—C201.398 (4)
C2—C31.375 (4)C16—C171.381 (4)
C2—H2A0.9300C16—H16A0.9300
C3—O21.369 (4)C17—C181.367 (4)
C3—C41.378 (4)C17—O41.393 (4)
C4—C51.379 (5)C18—C191.384 (5)
C4—H4A0.9300C18—H18A0.9300
C5—C61.384 (4)C19—C201.381 (5)
C5—H5A0.9300C19—H19A0.9300
C6—C71.519 (4)C20—C211.526 (4)
C7—C91.510 (5)C21—C231.523 (5)
C7—C81.538 (5)C21—C221.534 (5)
C7—H7A0.9800C21—H21A0.9800
C8—H8A0.9600C22—H22A0.9600
C8—H8B0.9600C22—H22B0.9600
C8—H8C0.9600C22—H22C0.9600
C9—C141.372 (5)C23—C241.383 (4)
C9—C101.387 (5)C23—C281.386 (5)
C10—C111.370 (6)C24—C251.378 (5)
C10—H10A0.9300C24—H24A0.9300
C11—C121.358 (5)C25—C261.358 (5)
C11—H11A0.9300C25—H25A0.9300
C12—C131.371 (5)C26—C271.367 (5)
C12—H12A0.9300C26—H26A0.9300
C13—C141.391 (5)C27—C281.379 (5)
C13—H13A0.9300C27—H27A0.9300
C14—H14A0.9300C28—H28A0.9300
O1—H10.8200O3—H30.8200
O2—H20.8200O4—H40.8200
O1—C1—C2118.0 (3)C16—C15—O3119.6 (3)
O1—C1—C6119.7 (3)C16—C15—C20122.0 (3)
C2—C1—C6122.3 (3)O3—C15—C20118.4 (3)
C3—C2—C1120.0 (3)C15—C16—C17119.6 (3)
C3—C2—H2A120.0C15—C16—H16A120.2
C1—C2—H2A120.0C17—C16—H16A120.2
O2—C3—C2118.3 (3)C18—C17—C16120.5 (3)
O2—C3—C4121.9 (3)C18—C17—O4120.3 (3)
C2—C3—C4119.8 (3)C16—C17—O4119.2 (3)
C3—C4—C5118.7 (3)C17—C18—C19118.8 (3)
C3—C4—H4A120.6C17—C18—H18A120.6
C5—C4—H4A120.6C19—C18—H18A120.6
C4—C5—C6123.8 (3)C20—C19—C18122.8 (3)
C4—C5—H5A118.1C20—C19—H19A118.6
C6—C5—H5A118.1C18—C19—H19A118.6
C5—C6—C1115.4 (3)C19—C20—C15116.3 (3)
C5—C6—C7124.4 (3)C19—C20—C21124.1 (3)
C1—C6—C7120.0 (3)C15—C20—C21119.6 (3)
C9—C7—C6115.0 (3)C23—C21—C20112.9 (2)
C9—C7—C8107.8 (3)C23—C21—C22109.9 (3)
C6—C7—C8113.6 (3)C20—C21—C22113.6 (3)
C9—C7—H7A106.6C23—C21—H21A106.7
C6—C7—H7A106.6C20—C21—H21A106.7
C8—C7—H7A106.6C22—C21—H21A106.7
C7—C8—H8A109.5C21—C22—H22A109.5
C7—C8—H8B109.5C21—C22—H22B109.5
H8A—C8—H8B109.5H22A—C22—H22B109.5
C7—C8—H8C109.5C21—C22—H22C109.5
H8A—C8—H8C109.5H22A—C22—H22C109.5
H8B—C8—H8C109.5H22B—C22—H22C109.5
C14—C9—C10117.8 (3)C24—C23—C28117.3 (3)
C14—C9—C7121.7 (3)C24—C23—C21121.6 (3)
C10—C9—C7120.5 (3)C28—C23—C21121.0 (3)
C11—C10—C9121.0 (4)C25—C24—C23121.1 (3)
C11—C10—H10A119.5C25—C24—H24A119.4
C9—C10—H10A119.5C23—C24—H24A119.4
C12—C11—C10120.9 (3)C26—C25—C24120.7 (3)
C12—C11—H11A119.5C26—C25—H25A119.7
C10—C11—H11A119.5C24—C25—H25A119.7
C11—C12—C13119.2 (4)C25—C26—C27119.4 (4)
C11—C12—H12A120.4C25—C26—H26A120.3
C13—C12—H12A120.4C27—C26—H26A120.3
C12—C13—C14120.1 (4)C26—C27—C28120.5 (3)
C12—C13—H13A119.9C26—C27—H27A119.8
C14—C13—H13A119.9C28—C27—H27A119.8
C9—C14—C13120.9 (3)C27—C28—C23121.0 (3)
C9—C14—H14A119.5C27—C28—H28A119.5
C13—C14—H14A119.5C23—C28—H28A119.5
C1—O1—H1109.5C15—O3—H3109.5
C3—O2—H2109.5C17—O4—H4109.5
O1—C1—C2—C3178.0 (3)O3—C15—C16—C17179.1 (3)
C6—C1—C2—C30.9 (4)C20—C15—C16—C170.6 (5)
C1—C2—C3—O2179.2 (3)C15—C16—C17—C180.8 (5)
C1—C2—C3—C42.3 (4)C15—C16—C17—O4179.1 (3)
O2—C3—C4—C5179.9 (3)C16—C17—C18—C190.5 (5)
C2—C3—C4—C51.6 (5)O4—C17—C18—C19179.4 (3)
C3—C4—C5—C60.4 (5)C17—C18—C19—C201.2 (5)
C4—C5—C6—C11.6 (4)C18—C19—C20—C152.5 (5)
C4—C5—C6—C7172.5 (3)C18—C19—C20—C21176.3 (3)
O1—C1—C6—C5179.9 (3)C16—C15—C20—C192.2 (4)
C2—C1—C6—C51.0 (4)O3—C15—C20—C19179.3 (3)
O1—C1—C6—C75.5 (4)C16—C15—C20—C21176.7 (3)
C2—C1—C6—C7173.4 (3)O3—C15—C20—C211.8 (4)
C5—C6—C7—C9124.6 (3)C19—C20—C21—C23118.7 (3)
C1—C6—C7—C961.6 (4)C15—C20—C21—C2362.6 (4)
C5—C6—C7—C80.4 (4)C19—C20—C21—C227.3 (4)
C1—C6—C7—C8173.5 (3)C15—C20—C21—C22171.5 (3)
C6—C7—C9—C1450.6 (4)C20—C21—C23—C2450.4 (4)
C8—C7—C9—C1477.3 (4)C22—C21—C23—C2477.5 (4)
C6—C7—C9—C10132.8 (3)C20—C21—C23—C28133.5 (3)
C8—C7—C9—C1099.3 (3)C22—C21—C23—C2898.5 (3)
C14—C9—C10—C112.1 (5)C28—C23—C24—C250.1 (5)
C7—C9—C10—C11174.6 (3)C21—C23—C24—C25176.1 (3)
C9—C10—C11—C121.4 (6)C23—C24—C25—C260.2 (5)
C10—C11—C12—C130.2 (6)C24—C25—C26—C270.1 (5)
C11—C12—C13—C141.0 (5)C25—C26—C27—C280.2 (5)
C10—C9—C14—C131.3 (5)C26—C27—C28—C230.5 (5)
C7—C9—C14—C13175.3 (3)C24—C23—C28—C270.4 (5)
C12—C13—C14—C90.2 (5)C21—C23—C28—C27175.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.821.942.745 (3)166
O3—H3···O20.821.982.797 (3)177
O4—H4···O1ii0.822.002.816 (3)170
Symmetry codes: (i) x1/2, y+2, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H14O2
Mr214.25
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)13.131 (4), 5.7841 (15), 30.046 (8)
V3)2282.0 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.47 × 0.41 × 0.36
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10800, 2536, 1675
Rint0.035
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.103, 1.03
No. of reflections2536
No. of parameters293
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.14

Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.821.942.745 (3)166
O3—H3···O20.821.982.797 (3)177
O4—H4···O1ii0.822.002.816 (3)170
Symmetry codes: (i) x1/2, y+2, z; (ii) x, y+1, z.
 

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