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In the title mol­ecule, C15H10O2, there are two mol­ecules in the asymmetric unit. The γ-pyrone ring makes a dihedral angle of 1.0 (1)° with the 2-phenyl substituent in one of the mol­ecules, while in the other mol­ecule the γ-pyrone ring makes a dihedral angle of 9.8 (1)° with the 2-phenyl substituent.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300730X/om6138sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680300730X/om6138Isup2.hkl
Contains datablock I

CCDC reference: 214813

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.108
  • Data-to-parameter ratio = 9.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.28 From the CIF: _reflns_number_total 3010 Count of symmetry unique reflns 3041 Completeness (_total/calc) 98.98% 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 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.

Comment top

Flavones and related compounds are known to exhibit a wide range of interesting biological activities (Agullo et al., 1997; Carlo et al., 1993; Miksicek, 1993; Wang et al., 1999). Flavone is the parent molecule of a number of flavones that have interesting modulatory activities at GABA-A receptors (Medina et al., 1998; Chebib & Johnston, 2000). The title compound, (I), was crystallized as part of an ongoing structure–activity study to determine the properties of these compounds that confer this activity in order to aid the design of more active compounds.

All bond lengths and angles in (I) are as expected.

Experimental top

The sample of flavone was obtained from Sigma–Aldrich.

Computing details top

Data collection: SMART (Bruker, 1995); cell refinement: SMART (Bruker, 1995); data reduction: SAINT-Plus (Bruker, 1995); 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); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A general view of the molecular structure of (I). Ellipsoids are drawn at the 50% probability level.
(I) top
Crystal data top
C15H10O2Dx = 1.367 Mg m3
Mr = 222.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 999 reflections
a = 8.281 (2) Åθ = 1.9–28.3°
b = 13.216 (4) ŵ = 0.09 mm1
c = 19.737 (6) ÅT = 150 K
V = 2159.9 (11) Å3Needle, colourless
Z = 80.40 × 0.25 × 0.25 mm
F(000) = 928
Data collection top
Bruker CCD
diffractometer
2762 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 28.3°, θmin = 1.9°
ω scansh = 1110
14562 measured reflectionsk = 1617
3010 independent reflectionsl = 2625
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.3747P]
where P = (Fo2 + 2Fc2)/3
3010 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C15H10O2V = 2159.9 (11) Å3
Mr = 222.23Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 8.281 (2) ŵ = 0.09 mm1
b = 13.216 (4) ÅT = 150 K
c = 19.737 (6) Å0.40 × 0.25 × 0.25 mm
Data collection top
Bruker CCD
diffractometer
2762 reflections with I > 2σ(I)
14562 measured reflectionsRint = 0.023
3010 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.08Δρmax = 0.36 e Å3
3010 reflectionsΔρmin = 0.18 e Å3
307 parameters
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
xyzUiso*/Ueq
C10.2855 (2)0.48559 (13)0.65481 (8)0.0189 (3)
C20.1875 (2)0.48815 (13)0.71538 (9)0.0191 (3)
H20.15900.42740.73590.023*
C30.1358 (2)0.57592 (13)0.74317 (8)0.0182 (3)
C40.2656 (2)0.67228 (13)0.65820 (8)0.0194 (3)
C50.3242 (2)0.58587 (14)0.62614 (8)0.0185 (3)
C60.4206 (2)0.59750 (14)0.56829 (9)0.0220 (4)
H60.46200.54070.54650.026*
C70.4546 (2)0.69302 (15)0.54343 (9)0.0244 (4)
H70.51760.70040.50470.029*
C80.3940 (3)0.77833 (14)0.57665 (9)0.0258 (4)
H80.41720.84240.55980.031*
C90.3001 (3)0.76891 (14)0.63422 (10)0.0247 (4)
H90.26080.82590.65640.030*
C100.0373 (2)0.58628 (14)0.80503 (9)0.0193 (3)
C110.0061 (2)0.68218 (14)0.82900 (9)0.0236 (4)
H110.02750.73960.80570.028*
C120.0989 (2)0.69257 (15)0.88726 (10)0.0256 (4)
H120.12840.75650.90250.031*
C130.1473 (2)0.60695 (14)0.92264 (9)0.0241 (4)
H130.20850.61360.96190.029*
C140.1044 (2)0.51118 (15)0.89941 (9)0.0242 (4)
H140.13680.45400.92320.029*
C150.0134 (2)0.50088 (14)0.84077 (9)0.0228 (4)
H150.01400.43670.82520.027*
O10.17254 (17)0.66789 (9)0.71594 (6)0.0218 (3)
O20.33425 (18)0.40662 (9)0.62837 (7)0.0256 (3)
C1'0.2329 (2)0.78726 (13)0.30713 (9)0.0216 (4)
C2'0.1327 (2)0.79240 (13)0.24713 (9)0.0213 (4)
H2'0.10200.73240.22610.026*
C3'0.0820 (2)0.88129 (14)0.22047 (9)0.0191 (3)
C4'0.2096 (2)0.97431 (14)0.30760 (9)0.0197 (3)
C5'0.2688 (2)0.88652 (14)0.33780 (9)0.0197 (4)
C6'0.3620 (2)0.89555 (14)0.39699 (9)0.0229 (4)
H6'0.40310.83790.41780.027*
C7'0.3925 (2)0.98929 (15)0.42425 (9)0.0247 (4)
H7'0.45350.99490.46360.030*
C8'0.3322 (3)1.07621 (15)0.39294 (10)0.0255 (4)
H8'0.35371.13930.41170.031*
C9'0.2412 (3)1.06983 (14)0.33455 (9)0.0241 (4)
H9'0.20191.12790.31360.029*
C10'0.0134 (2)0.89339 (13)0.15790 (8)0.0184 (3)
C11'0.0804 (2)0.98693 (14)0.14014 (9)0.0203 (3)
H11'0.06391.04300.16770.024*
C12'0.1717 (2)0.99610 (15)0.08126 (9)0.0225 (4)
H12'0.21701.05820.06980.027*
C13'0.1952 (2)0.91244 (15)0.03945 (9)0.0233 (4)
H13'0.25680.91830.00020.028*
C14'0.1265 (2)0.82080 (14)0.05662 (9)0.0252 (4)
H14'0.14140.76520.02840.030*
C15'0.0357 (2)0.81008 (14)0.11514 (9)0.0237 (4)
H15'0.01010.74790.12600.028*
O1'0.11737 (16)0.97239 (9)0.24973 (6)0.0200 (3)
O2'0.2861 (2)0.70752 (10)0.33057 (7)0.0299 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0212 (8)0.0169 (8)0.0186 (7)0.0000 (7)0.0028 (6)0.0002 (6)
C20.0238 (8)0.0145 (7)0.0189 (7)0.0020 (7)0.0024 (7)0.0016 (6)
C30.0195 (8)0.0178 (8)0.0174 (7)0.0003 (7)0.0028 (7)0.0014 (6)
C40.0207 (8)0.0209 (8)0.0164 (7)0.0001 (7)0.0020 (7)0.0000 (6)
C50.0195 (8)0.0179 (8)0.0182 (8)0.0016 (7)0.0047 (7)0.0022 (6)
C60.0239 (9)0.0213 (8)0.0208 (8)0.0021 (7)0.0021 (7)0.0025 (7)
C70.0270 (9)0.0275 (9)0.0188 (8)0.0023 (8)0.0027 (7)0.0030 (7)
C80.0340 (10)0.0190 (8)0.0244 (9)0.0049 (8)0.0000 (8)0.0052 (7)
C90.0336 (10)0.0187 (8)0.0220 (8)0.0010 (7)0.0002 (8)0.0006 (7)
C100.0176 (8)0.0234 (8)0.0168 (7)0.0022 (7)0.0030 (6)0.0009 (7)
C110.0273 (9)0.0232 (9)0.0202 (8)0.0007 (8)0.0002 (7)0.0001 (7)
C120.0314 (10)0.0228 (9)0.0227 (9)0.0016 (8)0.0003 (8)0.0051 (7)
C130.0218 (9)0.0304 (10)0.0200 (8)0.0011 (8)0.0015 (7)0.0046 (7)
C140.0231 (9)0.0251 (9)0.0243 (9)0.0036 (8)0.0006 (7)0.0002 (7)
C150.0235 (9)0.0205 (8)0.0243 (8)0.0000 (7)0.0010 (7)0.0017 (7)
O10.0289 (7)0.0147 (6)0.0219 (6)0.0009 (5)0.0025 (6)0.0008 (5)
O20.0356 (8)0.0169 (6)0.0243 (6)0.0026 (6)0.0031 (6)0.0017 (5)
C1'0.0256 (9)0.0195 (8)0.0196 (8)0.0013 (7)0.0023 (7)0.0011 (7)
C2'0.0264 (9)0.0162 (7)0.0213 (8)0.0006 (7)0.0029 (7)0.0018 (7)
C3'0.0201 (8)0.0196 (8)0.0175 (7)0.0004 (7)0.0023 (7)0.0026 (6)
C4'0.0191 (8)0.0234 (8)0.0166 (7)0.0011 (7)0.0016 (6)0.0013 (7)
C5'0.0211 (9)0.0197 (8)0.0184 (8)0.0018 (7)0.0041 (7)0.0018 (6)
C6'0.0247 (9)0.0238 (9)0.0203 (8)0.0005 (7)0.0010 (7)0.0026 (7)
C7'0.0248 (9)0.0307 (9)0.0185 (8)0.0031 (8)0.0022 (7)0.0025 (7)
C8'0.0298 (10)0.0219 (9)0.0246 (9)0.0043 (8)0.0011 (8)0.0053 (7)
C9'0.0273 (10)0.0215 (9)0.0234 (9)0.0012 (8)0.0000 (8)0.0003 (7)
C10'0.0175 (8)0.0213 (8)0.0163 (7)0.0012 (7)0.0014 (6)0.0006 (6)
C11'0.0208 (8)0.0208 (8)0.0194 (8)0.0004 (7)0.0026 (7)0.0016 (7)
C12'0.0213 (8)0.0240 (9)0.0223 (8)0.0013 (7)0.0020 (7)0.0046 (7)
C13'0.0211 (8)0.0324 (9)0.0164 (8)0.0038 (8)0.0009 (7)0.0028 (7)
C14'0.0318 (10)0.0245 (9)0.0193 (8)0.0047 (8)0.0002 (8)0.0037 (7)
C15'0.0278 (9)0.0201 (8)0.0232 (9)0.0010 (7)0.0013 (8)0.0005 (7)
O1'0.0247 (6)0.0156 (6)0.0198 (6)0.0012 (5)0.0028 (5)0.0008 (5)
O2'0.0423 (9)0.0199 (6)0.0274 (7)0.0048 (6)0.0077 (6)0.0018 (5)
Geometric parameters (Å, º) top
C1—O21.235 (2)C1'—O2'1.232 (2)
C1—C21.445 (2)C1'—C2'1.448 (2)
C1—C51.476 (2)C1'—C5'1.475 (2)
C2—C31.353 (2)C2'—C3'1.354 (2)
C2—H20.9300C2'—H2'0.9300
C3—O11.363 (2)C3'—O1'1.367 (2)
C3—C101.474 (2)C3'—C10'1.475 (2)
C4—O11.377 (2)C4'—O1'1.374 (2)
C4—C91.392 (2)C4'—C5'1.393 (2)
C4—C51.393 (2)C4'—C9'1.395 (3)
C5—C61.402 (2)C5'—C6'1.405 (3)
C6—C71.383 (3)C6'—C7'1.374 (3)
C6—H60.9300C6'—H6'0.9300
C7—C81.397 (3)C7'—C8'1.397 (3)
C7—H70.9300C7'—H7'0.9300
C8—C91.383 (3)C8'—C9'1.379 (3)
C8—H80.9300C8'—H8'0.9300
C9—H90.9300C9'—H9'0.9300
C10—C151.396 (2)C10'—C15'1.399 (2)
C10—C111.400 (3)C10'—C11'1.400 (2)
C11—C121.390 (3)C11'—C12'1.391 (2)
C11—H110.9300C11'—H11'0.9300
C12—C131.389 (3)C12'—C13'1.393 (3)
C12—H120.9300C12'—H12'0.9300
C13—C141.392 (3)C13'—C14'1.380 (3)
C13—H130.9300C13'—H13'0.9300
C14—C151.388 (3)C14'—C15'1.385 (3)
C14—H140.9300C14'—H14'0.9300
C15—H150.9300C15'—H15'0.9300
O2—C1—C2123.57 (16)O2'—C1'—C2'123.50 (16)
O2—C1—C5121.74 (15)O2'—C1'—C5'122.32 (16)
C2—C1—C5114.69 (15)C2'—C1'—C5'114.18 (15)
C3—C2—C1122.22 (15)C3'—C2'—C1'122.43 (16)
C3—C2—H2118.9C3'—C2'—H2'118.8
C1—C2—H2118.9C1'—C2'—H2'118.8
C2—C3—O1122.28 (15)C2'—C3'—O1'122.26 (15)
C2—C3—C10126.18 (15)C2'—C3'—C10'125.84 (16)
O1—C3—C10111.54 (14)O1'—C3'—C10'111.90 (14)
O1—C4—C9115.78 (15)O1'—C4'—C5'122.38 (15)
O1—C4—C5122.43 (15)O1'—C4'—C9'115.97 (16)
C9—C4—C5121.78 (16)C5'—C4'—C9'121.65 (16)
C4—C5—C6118.58 (16)C4'—C5'—C6'118.56 (16)
C4—C5—C1119.12 (15)C4'—C5'—C1'119.62 (16)
C6—C5—C1122.29 (16)C6'—C5'—C1'121.82 (16)
C7—C6—C5120.32 (17)C7'—C6'—C5'120.21 (17)
C7—C6—H6119.8C7'—C6'—H6'119.9
C5—C6—H6119.8C5'—C6'—H6'119.9
C6—C7—C8119.79 (16)C6'—C7'—C8'120.16 (17)
C6—C7—H7120.1C6'—C7'—H7'119.9
C8—C7—H7120.1C8'—C7'—H7'119.9
C9—C8—C7120.99 (16)C9'—C8'—C7'120.98 (17)
C9—C8—H8119.5C9'—C8'—H8'119.5
C7—C8—H8119.5C7'—C8'—H8'119.5
C8—C9—C4118.52 (17)C8'—C9'—C4'118.45 (17)
C8—C9—H9120.7C8'—C9'—H9'120.8
C4—C9—H9120.7C4'—C9'—H9'120.8
C15—C10—C11118.95 (16)C15'—C10'—C11'119.43 (16)
C15—C10—C3120.65 (16)C15'—C10'—C3'119.37 (16)
C11—C10—C3120.40 (16)C11'—C10'—C3'121.19 (15)
C12—C11—C10120.75 (17)C12'—C11'—C10'120.09 (16)
C12—C11—H11119.6C12'—C11'—H11'120.0
C10—C11—H11119.6C10'—C11'—H11'120.0
C13—C12—C11119.67 (17)C11'—C12'—C13'120.10 (17)
C13—C12—H12120.2C11'—C12'—H12'119.9
C11—C12—H12120.2C13'—C12'—H12'119.9
C12—C13—C14120.11 (17)C14'—C13'—C12'119.55 (17)
C12—C13—H13119.9C14'—C13'—H13'120.2
C14—C13—H13119.9C12'—C13'—H13'120.2
C15—C14—C13120.15 (17)C13'—C14'—C15'121.20 (17)
C15—C14—H14119.9C13'—C14'—H14'119.4
C13—C14—H14119.9C15'—C14'—H14'119.4
C14—C15—C10120.37 (17)C14'—C15'—C10'119.61 (17)
C14—C15—H15119.8C14'—C15'—H15'120.2
C10—C15—H15119.8C10'—C15'—H15'120.2
C3—O1—C4119.26 (13)C3'—O1'—C4'119.10 (13)
O2—C1—C2—C3179.96 (18)O2'—C1'—C2'—C3'176.77 (19)
C5—C1—C2—C30.0 (2)C5'—C1'—C2'—C3'2.3 (3)
C1—C2—C3—O10.0 (3)C1'—C2'—C3'—O1'2.3 (3)
C1—C2—C3—C10179.26 (16)C1'—C2'—C3'—C10'176.90 (16)
O1—C4—C5—C6178.81 (16)O1'—C4'—C5'—C6'179.91 (16)
C9—C4—C5—C60.2 (3)C9'—C4'—C5'—C6'0.2 (3)
O1—C4—C5—C10.0 (2)O1'—C4'—C5'—C1'0.2 (3)
C9—C4—C5—C1178.96 (17)C9'—C4'—C5'—C1'179.63 (18)
O2—C1—C5—C4179.94 (17)O2'—C1'—C5'—C4'177.81 (19)
C2—C1—C5—C40.1 (2)C2'—C1'—C5'—C4'1.3 (2)
O2—C1—C5—C61.3 (3)O2'—C1'—C5'—C6'2.0 (3)
C2—C1—C5—C6178.71 (16)C2'—C1'—C5'—C6'178.86 (17)
C4—C5—C6—C70.8 (3)C4'—C5'—C6'—C7'0.4 (3)
C1—C5—C6—C7179.58 (17)C1'—C5'—C6'—C7'179.79 (18)
C5—C6—C7—C80.7 (3)C5'—C6'—C7'—C8'0.5 (3)
C6—C7—C8—C90.0 (3)C6'—C7'—C8'—C9'0.1 (3)
C7—C8—C9—C40.6 (3)C7'—C8'—C9'—C4'0.5 (3)
O1—C4—C9—C8179.58 (16)O1'—C4'—C9'—C8'179.48 (16)
C5—C4—C9—C80.5 (3)C5'—C4'—C9'—C8'0.6 (3)
C2—C3—C10—C150.7 (3)C2'—C3'—C10'—C15'10.5 (3)
O1—C3—C10—C15179.98 (16)O1'—C3'—C10'—C15'168.72 (16)
C2—C3—C10—C11179.04 (18)C2'—C3'—C10'—C11'170.21 (18)
O1—C3—C10—C110.3 (2)O1'—C3'—C10'—C11'10.5 (2)
C15—C10—C11—C120.3 (3)C15'—C10'—C11'—C12'1.6 (3)
C3—C10—C11—C12180.00 (17)C3'—C10'—C11'—C12'179.20 (16)
C10—C11—C12—C130.9 (3)C10'—C11'—C12'—C13'0.7 (3)
C11—C12—C13—C140.7 (3)C11'—C12'—C13'—C14'0.5 (3)
C12—C13—C14—C150.1 (3)C12'—C13'—C14'—C15'0.7 (3)
C13—C14—C15—C100.7 (3)C13'—C14'—C15'—C10'0.2 (3)
C11—C10—C15—C140.5 (3)C11'—C10'—C15'—C14'1.3 (3)
C3—C10—C15—C14179.23 (16)C3'—C10'—C15'—C14'179.41 (17)
C2—C3—O1—C40.1 (2)C2'—C3'—O1'—C4'1.1 (2)
C10—C3—O1—C4179.29 (14)C10'—C3'—O1'—C4'178.25 (14)
C9—C4—O1—C3178.94 (16)C5'—C4'—O1'—C3'0.0 (2)
C5—C4—O1—C30.1 (2)C9'—C4'—O1'—C3'179.84 (16)

Experimental details

Crystal data
Chemical formulaC15H10O2
Mr222.23
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)8.281 (2), 13.216 (4), 19.737 (6)
V3)2159.9 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.25 × 0.25
Data collection
DiffractometerBruker CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14562, 3010, 2762
Rint0.023
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.108, 1.08
No. of reflections3010
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.18

Computer programs: SMART (Bruker, 1995), SAINT-Plus (Bruker, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

 

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