Flavone

Waller, M.P.; Hibbs, D.E.; Overgaard, J.; Hanrahan, J.R.; Hambley, T.W.

doi:10.1107/S160053680300730X

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Flavone

M. P. Waller, D. E. Hibbs, J. Overgaard, J. R. Hanrahan and T. W. Hambley

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300730X/om6138sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300730X/om6138Isup2.hkl Contains datablock I

CCDC reference: 214813

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (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

Fig. 1. A general view of the molecular structure of (I). Ellipsoids are drawn at the 50% probability level.

(I) top

Crystal data top

C₁₅H₁₀O₂	D_x = 1.367 Mg m⁻³
M_r = 222.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 999 reflections
a = 8.281 (2) Å	θ = 1.9–28.3°
b = 13.216 (4) Å	µ = 0.09 mm⁻¹
c = 19.737 (6) Å	T = 150 K
V = 2159.9 (11) Å³	Needle, colourless
Z = 8	0.40 × 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 tube	R_int = 0.023
Graphite monochromator	θ_max = 28.3°, θ_min = 1.9°
ω scans	h = −11→10
14562 measured reflections	k = −16→17
3010 independent reflections	l = −26→25

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0679P)² + 0.3747P] where P = (F_o² + 2F_c²)/3
3010 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₀O₂	V = 2159.9 (11) Å³
M_r = 222.23	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.281 (2) Å	µ = 0.09 mm⁻¹
b = 13.216 (4) Å	T = 150 K
c = 19.737 (6) Å	0.40 × 0.25 × 0.25 mm

Data collection top

Bruker CCD diffractometer	2762 reflections with I > 2σ(I)
14562 measured reflections	R_int = 0.023
3010 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.08	Δρ_max = 0.36 e Å⁻³
3010 reflections	Δρ_min = −0.18 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.2855 (2)	0.48559 (13)	0.65481 (8)	0.0189 (3)
C2	0.1875 (2)	0.48815 (13)	0.71538 (9)	0.0191 (3)
H2	0.1590	0.4274	0.7359	0.023*
C3	0.1358 (2)	0.57592 (13)	0.74317 (8)	0.0182 (3)
C4	0.2656 (2)	0.67228 (13)	0.65820 (8)	0.0194 (3)
C5	0.3242 (2)	0.58587 (14)	0.62614 (8)	0.0185 (3)
C6	0.4206 (2)	0.59750 (14)	0.56829 (9)	0.0220 (4)
H6	0.4620	0.5407	0.5465	0.026*
C7	0.4546 (2)	0.69302 (15)	0.54343 (9)	0.0244 (4)
H7	0.5176	0.7004	0.5047	0.029*
C8	0.3940 (3)	0.77833 (14)	0.57665 (9)	0.0258 (4)
H8	0.4172	0.8424	0.5598	0.031*
C9	0.3001 (3)	0.76891 (14)	0.63422 (10)	0.0247 (4)
H9	0.2608	0.8259	0.6564	0.030*
C10	0.0373 (2)	0.58628 (14)	0.80503 (9)	0.0193 (3)
C11	−0.0061 (2)	0.68218 (14)	0.82900 (9)	0.0236 (4)
H11	0.0275	0.7396	0.8057	0.028*
C12	−0.0989 (2)	0.69257 (15)	0.88726 (10)	0.0256 (4)
H12	−0.1284	0.7565	0.9025	0.031*
C13	−0.1473 (2)	0.60695 (14)	0.92264 (9)	0.0241 (4)
H13	−0.2085	0.6136	0.9619	0.029*
C14	−0.1044 (2)	0.51118 (15)	0.89941 (9)	0.0242 (4)
H14	−0.1368	0.4540	0.9232	0.029*
C15	−0.0134 (2)	0.50088 (14)	0.84077 (9)	0.0228 (4)
H15	0.0140	0.4367	0.8252	0.027*
O1	0.17254 (17)	0.66789 (9)	0.71594 (6)	0.0218 (3)
O2	0.33425 (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'	0.1020	0.7324	0.2261	0.026*
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'	0.4031	0.8379	0.4178	0.027*
C7'	0.3925 (2)	0.98929 (15)	0.42425 (9)	0.0247 (4)
H7'	0.4535	0.9949	0.4636	0.030*
C8'	0.3322 (3)	1.07621 (15)	0.39294 (10)	0.0255 (4)
H8'	0.3537	1.1393	0.4117	0.031*
C9'	0.2412 (3)	1.06983 (14)	0.33455 (9)	0.0241 (4)
H9'	0.2019	1.1279	0.3136	0.029*
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'	−0.0639	1.0430	0.1677	0.024*
C12'	−0.1717 (2)	0.99610 (15)	0.08126 (9)	0.0225 (4)
H12'	−0.2170	1.0582	0.0698	0.027*
C13'	−0.1952 (2)	0.91244 (15)	0.03945 (9)	0.0233 (4)
H13'	−0.2568	0.9183	0.0002	0.028*
C14'	−0.1265 (2)	0.82080 (14)	0.05662 (9)	0.0252 (4)
H14'	−0.1414	0.7652	0.0284	0.030*
C15'	−0.0357 (2)	0.81008 (14)	0.11514 (9)	0.0237 (4)
H15'	0.0101	0.7479	0.1260	0.028*
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

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0212 (8)	0.0169 (8)	0.0186 (7)	0.0000 (7)	−0.0028 (6)	−0.0002 (6)
C2	0.0238 (8)	0.0145 (7)	0.0189 (7)	−0.0020 (7)	−0.0024 (7)	0.0016 (6)
C3	0.0195 (8)	0.0178 (8)	0.0174 (7)	−0.0003 (7)	−0.0028 (7)	0.0014 (6)
C4	0.0207 (8)	0.0209 (8)	0.0164 (7)	−0.0001 (7)	−0.0020 (7)	0.0000 (6)
C5	0.0195 (8)	0.0179 (8)	0.0182 (8)	−0.0016 (7)	−0.0047 (7)	0.0022 (6)
C6	0.0239 (9)	0.0213 (8)	0.0208 (8)	0.0021 (7)	−0.0021 (7)	−0.0025 (7)
C7	0.0270 (9)	0.0275 (9)	0.0188 (8)	−0.0023 (8)	0.0027 (7)	0.0030 (7)
C8	0.0340 (10)	0.0190 (8)	0.0244 (9)	−0.0049 (8)	0.0000 (8)	0.0052 (7)
C9	0.0336 (10)	0.0187 (8)	0.0220 (8)	0.0010 (7)	0.0002 (8)	0.0006 (7)
C10	0.0176 (8)	0.0234 (8)	0.0168 (7)	0.0022 (7)	−0.0030 (6)	−0.0009 (7)
C11	0.0273 (9)	0.0232 (9)	0.0202 (8)	−0.0007 (8)	0.0002 (7)	0.0001 (7)
C12	0.0314 (10)	0.0228 (9)	0.0227 (9)	0.0016 (8)	−0.0003 (8)	−0.0051 (7)
C13	0.0218 (9)	0.0304 (10)	0.0200 (8)	−0.0011 (8)	0.0015 (7)	−0.0046 (7)
C14	0.0231 (9)	0.0251 (9)	0.0243 (9)	−0.0036 (8)	−0.0006 (7)	0.0002 (7)
C15	0.0235 (9)	0.0205 (8)	0.0243 (8)	0.0000 (7)	−0.0010 (7)	−0.0017 (7)
O1	0.0289 (7)	0.0147 (6)	0.0219 (6)	0.0009 (5)	0.0025 (6)	0.0008 (5)
O2	0.0356 (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—O2	1.235 (2)	C1'—O2'	1.232 (2)
C1—C2	1.445 (2)	C1'—C2'	1.448 (2)
C1—C5	1.476 (2)	C1'—C5'	1.475 (2)
C2—C3	1.353 (2)	C2'—C3'	1.354 (2)
C2—H2	0.9300	C2'—H2'	0.9300
C3—O1	1.363 (2)	C3'—O1'	1.367 (2)
C3—C10	1.474 (2)	C3'—C10'	1.475 (2)
C4—O1	1.377 (2)	C4'—O1'	1.374 (2)
C4—C9	1.392 (2)	C4'—C5'	1.393 (2)
C4—C5	1.393 (2)	C4'—C9'	1.395 (3)
C5—C6	1.402 (2)	C5'—C6'	1.405 (3)
C6—C7	1.383 (3)	C6'—C7'	1.374 (3)
C6—H6	0.9300	C6'—H6'	0.9300
C7—C8	1.397 (3)	C7'—C8'	1.397 (3)
C7—H7	0.9300	C7'—H7'	0.9300
C8—C9	1.383 (3)	C8'—C9'	1.379 (3)
C8—H8	0.9300	C8'—H8'	0.9300
C9—H9	0.9300	C9'—H9'	0.9300
C10—C15	1.396 (2)	C10'—C15'	1.399 (2)
C10—C11	1.400 (3)	C10'—C11'	1.400 (2)
C11—C12	1.390 (3)	C11'—C12'	1.391 (2)
C11—H11	0.9300	C11'—H11'	0.9300
C12—C13	1.389 (3)	C12'—C13'	1.393 (3)
C12—H12	0.9300	C12'—H12'	0.9300
C13—C14	1.392 (3)	C13'—C14'	1.380 (3)
C13—H13	0.9300	C13'—H13'	0.9300
C14—C15	1.388 (3)	C14'—C15'	1.385 (3)
C14—H14	0.9300	C14'—H14'	0.9300
C15—H15	0.9300	C15'—H15'	0.9300

O2—C1—C2	123.57 (16)	O2'—C1'—C2'	123.50 (16)
O2—C1—C5	121.74 (15)	O2'—C1'—C5'	122.32 (16)
C2—C1—C5	114.69 (15)	C2'—C1'—C5'	114.18 (15)
C3—C2—C1	122.22 (15)	C3'—C2'—C1'	122.43 (16)
C3—C2—H2	118.9	C3'—C2'—H2'	118.8
C1—C2—H2	118.9	C1'—C2'—H2'	118.8
C2—C3—O1	122.28 (15)	C2'—C3'—O1'	122.26 (15)
C2—C3—C10	126.18 (15)	C2'—C3'—C10'	125.84 (16)
O1—C3—C10	111.54 (14)	O1'—C3'—C10'	111.90 (14)
O1—C4—C9	115.78 (15)	O1'—C4'—C5'	122.38 (15)
O1—C4—C5	122.43 (15)	O1'—C4'—C9'	115.97 (16)
C9—C4—C5	121.78 (16)	C5'—C4'—C9'	121.65 (16)
C4—C5—C6	118.58 (16)	C4'—C5'—C6'	118.56 (16)
C4—C5—C1	119.12 (15)	C4'—C5'—C1'	119.62 (16)
C6—C5—C1	122.29 (16)	C6'—C5'—C1'	121.82 (16)
C7—C6—C5	120.32 (17)	C7'—C6'—C5'	120.21 (17)
C7—C6—H6	119.8	C7'—C6'—H6'	119.9
C5—C6—H6	119.8	C5'—C6'—H6'	119.9
C6—C7—C8	119.79 (16)	C6'—C7'—C8'	120.16 (17)
C6—C7—H7	120.1	C6'—C7'—H7'	119.9
C8—C7—H7	120.1	C8'—C7'—H7'	119.9
C9—C8—C7	120.99 (16)	C9'—C8'—C7'	120.98 (17)
C9—C8—H8	119.5	C9'—C8'—H8'	119.5
C7—C8—H8	119.5	C7'—C8'—H8'	119.5
C8—C9—C4	118.52 (17)	C8'—C9'—C4'	118.45 (17)
C8—C9—H9	120.7	C8'—C9'—H9'	120.8
C4—C9—H9	120.7	C4'—C9'—H9'	120.8
C15—C10—C11	118.95 (16)	C15'—C10'—C11'	119.43 (16)
C15—C10—C3	120.65 (16)	C15'—C10'—C3'	119.37 (16)
C11—C10—C3	120.40 (16)	C11'—C10'—C3'	121.19 (15)
C12—C11—C10	120.75 (17)	C12'—C11'—C10'	120.09 (16)
C12—C11—H11	119.6	C12'—C11'—H11'	120.0
C10—C11—H11	119.6	C10'—C11'—H11'	120.0
C13—C12—C11	119.67 (17)	C11'—C12'—C13'	120.10 (17)
C13—C12—H12	120.2	C11'—C12'—H12'	119.9
C11—C12—H12	120.2	C13'—C12'—H12'	119.9
C12—C13—C14	120.11 (17)	C14'—C13'—C12'	119.55 (17)
C12—C13—H13	119.9	C14'—C13'—H13'	120.2
C14—C13—H13	119.9	C12'—C13'—H13'	120.2
C15—C14—C13	120.15 (17)	C13'—C14'—C15'	121.20 (17)
C15—C14—H14	119.9	C13'—C14'—H14'	119.4
C13—C14—H14	119.9	C15'—C14'—H14'	119.4
C14—C15—C10	120.37 (17)	C14'—C15'—C10'	119.61 (17)
C14—C15—H15	119.8	C14'—C15'—H15'	120.2
C10—C15—H15	119.8	C10'—C15'—H15'	120.2
C3—O1—C4	119.26 (13)	C3'—O1'—C4'	119.10 (13)

O2—C1—C2—C3	−179.96 (18)	O2'—C1'—C2'—C3'	−176.77 (19)
C5—C1—C2—C3	0.0 (2)	C5'—C1'—C2'—C3'	2.3 (3)
C1—C2—C3—O1	0.0 (3)	C1'—C2'—C3'—O1'	−2.3 (3)
C1—C2—C3—C10	−179.26 (16)	C1'—C2'—C3'—C10'	176.90 (16)
O1—C4—C5—C6	−178.81 (16)	O1'—C4'—C5'—C6'	−179.91 (16)
C9—C4—C5—C6	0.2 (3)	C9'—C4'—C5'—C6'	0.2 (3)
O1—C4—C5—C1	0.0 (2)	O1'—C4'—C5'—C1'	0.2 (3)
C9—C4—C5—C1	178.96 (17)	C9'—C4'—C5'—C1'	−179.63 (18)
O2—C1—C5—C4	179.94 (17)	O2'—C1'—C5'—C4'	177.81 (19)
C2—C1—C5—C4	−0.1 (2)	C2'—C1'—C5'—C4'	−1.3 (2)
O2—C1—C5—C6	−1.3 (3)	O2'—C1'—C5'—C6'	−2.0 (3)
C2—C1—C5—C6	178.71 (16)	C2'—C1'—C5'—C6'	178.86 (17)
C4—C5—C6—C7	−0.8 (3)	C4'—C5'—C6'—C7'	0.4 (3)
C1—C5—C6—C7	−179.58 (17)	C1'—C5'—C6'—C7'	−179.79 (18)
C5—C6—C7—C8	0.7 (3)	C5'—C6'—C7'—C8'	−0.5 (3)
C6—C7—C8—C9	0.0 (3)	C6'—C7'—C8'—C9'	0.1 (3)
C7—C8—C9—C4	−0.6 (3)	C7'—C8'—C9'—C4'	0.5 (3)
O1—C4—C9—C8	179.58 (16)	O1'—C4'—C9'—C8'	179.48 (16)
C5—C4—C9—C8	0.5 (3)	C5'—C4'—C9'—C8'	−0.6 (3)
C2—C3—C10—C15	−0.7 (3)	C2'—C3'—C10'—C15'	−10.5 (3)
O1—C3—C10—C15	179.98 (16)	O1'—C3'—C10'—C15'	168.72 (16)
C2—C3—C10—C11	179.04 (18)	C2'—C3'—C10'—C11'	170.21 (18)
O1—C3—C10—C11	−0.3 (2)	O1'—C3'—C10'—C11'	−10.5 (2)
C15—C10—C11—C12	−0.3 (3)	C15'—C10'—C11'—C12'	1.6 (3)
C3—C10—C11—C12	180.00 (17)	C3'—C10'—C11'—C12'	−179.20 (16)
C10—C11—C12—C13	0.9 (3)	C10'—C11'—C12'—C13'	−0.7 (3)
C11—C12—C13—C14	−0.7 (3)	C11'—C12'—C13'—C14'	−0.5 (3)
C12—C13—C14—C15	−0.1 (3)	C12'—C13'—C14'—C15'	0.7 (3)
C13—C14—C15—C10	0.7 (3)	C13'—C14'—C15'—C10'	0.2 (3)
C11—C10—C15—C14	−0.5 (3)	C11'—C10'—C15'—C14'	−1.3 (3)
C3—C10—C15—C14	179.23 (16)	C3'—C10'—C15'—C14'	179.41 (17)
C2—C3—O1—C4	−0.1 (2)	C2'—C3'—O1'—C4'	1.1 (2)
C10—C3—O1—C4	179.29 (14)	C10'—C3'—O1'—C4'	−178.25 (14)
C9—C4—O1—C3	−178.94 (16)	C5'—C4'—O1'—C3'	0.0 (2)
C5—C4—O1—C3	0.1 (2)	C9'—C4'—O1'—C3'	179.84 (16)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀O₂
M_r	222.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	8.281 (2), 13.216 (4), 19.737 (6)
V (Å³)	2159.9 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.25 × 0.25

Data collection
Diffractometer	Bruker CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14562, 3010, 2762
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.108, 1.08
No. of reflections	3010
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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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