5,7-Bis(benz-yloxy)-2-[4-(benz-yloxy)phen-yl]-4H-chromen-4-one.

In the title compound, C(36)H(28)O(5), the terminal benzene rings are twisted at dihedral angles of 6.75 (12), 70.86 (14) and 82.02 (12)° with the respect to the central plana r[maximum deviation = 0.070 (3) Å] chromen-4-one ring system. In the crystal structure, π-π stacking is observed between parallel benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.7459 (16) Å].

Related literature

For general background to the biological effects of flavones, see: Formica & Regelson (1995 ▶); Medina et al. (1998 ▶); Cotelle et al. (1992 ▶). For a related structure, see: Waller et al. (2003 ▶).

Experimental

Crystal data

C36H28O5

M = 540.58

Triclinic,

a = 7.3176 (12) Å

b = 12.818 (2) Å

c = 14.933 (2) Å

α = 82.542 (3)°

β = 83.861 (3)°

γ = 85.600 (3)°

V = 1378.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.22 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

7198 measured reflections

4786 independent reflections

2505 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.140

S = 0.99

4786 reflections

370 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051678/xu2692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051678/xu2692Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C36H28O5	Z = 2
Mr = 540.58	F(000) = 568
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3176 (12) Å	Cell parameters from 1081 reflections
b = 12.818 (2) Å	θ = 2.2–21.3°
c = 14.933 (2) Å	µ = 0.09 mm−1
α = 82.542 (3)°	T = 293 K
β = 83.861 (3)°	Platelet, colorless
γ = 85.600 (3)°	0.35 × 0.22 × 0.08 mm
V = 1378.0 (4) Å3

Bruker SMART APEX CCD area-detector diffractometer	2505 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 25.0°, θmin = 1.4°
φ and ω scans	h = −8→7
7198 measured reflections	k = −15→14
4786 independent reflections	l = −17→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.0156P] where P = (Fo2 + 2Fc2)/3
4786 reflections	(Δ/σ)max < 0.001
370 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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	0.4399 (4)	0.5313 (2)	0.65974 (17)	0.0615 (7)
C2	0.3089 (3)	0.6140 (2)	0.65568 (17)	0.0637 (7)
H2	0.2078	0.6118	0.6233	0.076*
C3	0.3274 (4)	0.7009 (2)	0.69977 (19)	0.0650 (8)
C4	0.4748 (3)	0.7066 (2)	0.74818 (18)	0.0666 (8)
H4	0.4882	0.7653	0.7770	0.080*
C5	0.6029 (3)	0.6210 (2)	0.75215 (17)	0.0569 (7)
C6	0.5971 (3)	0.5329 (2)	0.70836 (17)	0.0578 (7)
C7	0.7481 (4)	0.4513 (2)	0.71387 (19)	0.0646 (7)
C8	0.8810 (4)	0.4680 (2)	0.77456 (18)	0.0649 (7)
H8	0.9751	0.4161	0.7845	0.078*
C9	0.8767 (3)	0.5535 (2)	0.81716 (17)	0.0567 (7)
C10	0.2776 (4)	0.4369 (2)	0.56895 (18)	0.0717 (8)
H10A	0.2759	0.4939	0.5195	0.086*
H10B	0.1631	0.4428	0.6078	0.086*
C11	0.2968 (4)	0.3326 (2)	0.53217 (17)	0.0658 (7)
C12	0.4499 (4)	0.2647 (2)	0.53946 (18)	0.0764 (8)
H12	0.5462	0.2817	0.5697	0.092*
C13	0.4618 (5)	0.1707 (3)	0.5019 (2)	0.0919 (10)
H13	0.5659	0.1248	0.5073	0.110*
C14	0.3212 (6)	0.1451 (3)	0.4571 (2)	0.1017 (11)
H14	0.3297	0.0821	0.4316	0.122*
C15	0.1680 (6)	0.2126 (3)	0.4499 (2)	0.1067 (12)
H15	0.0720	0.1956	0.4194	0.128*
C16	0.1558 (4)	0.3050 (3)	0.4874 (2)	0.0909 (10)
H16	0.0505	0.3500	0.4826	0.109*
C17	0.1970 (4)	0.8678 (2)	0.7378 (2)	0.0819 (9)
H17A	0.3049	0.9057	0.7139	0.098*
H17B	0.2055	0.8452	0.8018	0.098*
C18	0.0252 (4)	0.9384 (2)	0.7251 (2)	0.0664 (8)
C19	0.0278 (4)	1.0262 (2)	0.6621 (2)	0.0863 (10)
H19	0.1349	1.0402	0.6244	0.104*
C20	−0.1269 (6)	1.0941 (3)	0.6540 (2)	0.1007 (11)
H20	−0.1230	1.1539	0.6115	0.121*
C21	−0.2839 (5)	1.0739 (3)	0.7077 (2)	0.0919 (11)
H21	−0.3878	1.1199	0.7021	0.110*
C22	−0.2905 (4)	0.9869 (3)	0.7696 (2)	0.0881 (10)
H22	−0.3990	0.9730	0.8063	0.106*
C23	−0.1360 (4)	0.9187 (2)	0.7783 (2)	0.0807 (9)
H23	−0.1414	0.8588	0.8207	0.097*
C24	1.0066 (3)	0.5790 (2)	0.87816 (17)	0.0545 (7)
C25	1.1804 (3)	0.5272 (2)	0.88121 (17)	0.0605 (7)
H25	1.2117	0.4714	0.8473	0.073*
C26	1.3063 (4)	0.5567 (2)	0.93301 (17)	0.0638 (7)
H26	1.4220	0.5213	0.9335	0.077*
C27	1.2622 (4)	0.6387 (2)	0.98449 (17)	0.0610 (7)
C28	1.0861 (4)	0.6875 (2)	0.98691 (18)	0.0695 (8)
H28	1.0524	0.7401	1.0240	0.083*
C29	0.9617 (4)	0.6573 (2)	0.93393 (18)	0.0656 (7)
H29	0.8440	0.6905	0.9356	0.079*
C30	1.3635 (4)	0.7560 (2)	1.0795 (2)	0.0817 (9)
H30A	1.2865	0.7359	1.1351	0.098*
H30B	1.2981	0.8127	1.0439	0.098*
C31	1.5407 (4)	0.7924 (2)	1.1012 (2)	0.0676 (8)
C32	1.6274 (5)	0.8700 (3)	1.0444 (2)	0.0886 (10)
H32	1.5782	0.8973	0.9907	0.106*
C33	1.7863 (6)	0.9085 (3)	1.0654 (3)	0.1061 (12)
H33	1.8439	0.9613	1.0263	0.127*
C34	1.8587 (5)	0.8682 (4)	1.1447 (4)	0.1072 (13)
H34	1.9651	0.8941	1.1598	0.129*
C35	1.7749 (5)	0.7903 (3)	1.2013 (3)	0.0928 (10)
H35	1.8257	0.7624	1.2544	0.111*
C36	1.6151 (4)	0.7525 (2)	1.1804 (2)	0.0796 (9)
H36	1.5576	0.7000	1.2198	0.096*
O1	0.7420 (2)	0.63213 (13)	0.80484 (12)	0.0647 (5)
O2	0.7642 (3)	0.37370 (17)	0.67264 (15)	0.0968 (7)
O3	0.4297 (2)	0.44352 (14)	0.61951 (12)	0.0745 (6)
O4	0.1888 (2)	0.77832 (14)	0.69079 (13)	0.0772 (6)
O5	1.4013 (2)	0.66769 (14)	1.02937 (13)	0.0767 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0644 (18)	0.0570 (18)	0.0630 (18)	0.0071 (15)	−0.0114 (15)	−0.0095 (14)
C2	0.0628 (18)	0.0577 (18)	0.0724 (19)	0.0051 (15)	−0.0217 (14)	−0.0080 (14)
C3	0.0576 (17)	0.0521 (17)	0.084 (2)	0.0097 (15)	−0.0182 (15)	−0.0008 (15)
C4	0.0617 (18)	0.0525 (17)	0.087 (2)	0.0054 (15)	−0.0198 (16)	−0.0087 (14)
C5	0.0465 (16)	0.0557 (17)	0.0681 (18)	−0.0016 (14)	−0.0129 (14)	−0.0010 (14)
C6	0.0569 (17)	0.0540 (17)	0.0605 (17)	0.0012 (14)	−0.0054 (14)	−0.0028 (13)
C7	0.0580 (18)	0.0626 (19)	0.072 (2)	0.0110 (15)	−0.0102 (15)	−0.0101 (15)
C8	0.0578 (17)	0.0625 (19)	0.0726 (19)	0.0160 (14)	−0.0137 (15)	−0.0076 (15)
C9	0.0478 (16)	0.0530 (17)	0.0656 (18)	0.0075 (14)	−0.0063 (14)	0.0016 (14)
C10	0.0716 (19)	0.076 (2)	0.0697 (19)	0.0089 (16)	−0.0236 (16)	−0.0123 (15)
C11	0.078 (2)	0.0660 (19)	0.0535 (17)	0.0057 (17)	−0.0148 (15)	−0.0061 (14)
C12	0.091 (2)	0.071 (2)	0.0679 (19)	0.0125 (18)	−0.0205 (16)	−0.0140 (16)
C13	0.120 (3)	0.081 (2)	0.075 (2)	0.018 (2)	−0.014 (2)	−0.0175 (18)
C14	0.160 (4)	0.080 (2)	0.069 (2)	−0.002 (3)	−0.021 (2)	−0.0232 (18)
C15	0.140 (3)	0.099 (3)	0.092 (3)	−0.011 (3)	−0.043 (2)	−0.024 (2)
C16	0.098 (3)	0.091 (3)	0.090 (2)	0.010 (2)	−0.041 (2)	−0.020 (2)
C17	0.078 (2)	0.066 (2)	0.109 (2)	0.0175 (16)	−0.0397 (18)	−0.0230 (18)
C18	0.068 (2)	0.0559 (18)	0.079 (2)	0.0085 (16)	−0.0256 (17)	−0.0155 (15)
C19	0.083 (2)	0.083 (2)	0.089 (2)	0.0090 (19)	−0.0125 (18)	−0.0008 (19)
C20	0.116 (3)	0.077 (2)	0.105 (3)	0.024 (2)	−0.028 (2)	0.005 (2)
C21	0.099 (3)	0.085 (3)	0.093 (3)	0.038 (2)	−0.032 (2)	−0.026 (2)
C22	0.072 (2)	0.105 (3)	0.088 (2)	0.014 (2)	−0.0149 (18)	−0.023 (2)
C23	0.087 (2)	0.069 (2)	0.086 (2)	0.0047 (19)	−0.0244 (19)	−0.0023 (16)
C24	0.0492 (16)	0.0534 (16)	0.0576 (17)	0.0075 (13)	−0.0050 (13)	−0.0003 (13)
C25	0.0590 (17)	0.0578 (17)	0.0649 (18)	0.0097 (14)	−0.0118 (14)	−0.0120 (13)
C26	0.0600 (17)	0.0620 (18)	0.0685 (19)	0.0157 (15)	−0.0137 (15)	−0.0101 (15)
C27	0.0597 (18)	0.0608 (18)	0.0623 (18)	0.0112 (15)	−0.0166 (14)	−0.0071 (14)
C28	0.0677 (19)	0.0695 (19)	0.072 (2)	0.0157 (16)	−0.0138 (16)	−0.0195 (15)
C29	0.0576 (17)	0.0646 (19)	0.0727 (19)	0.0156 (14)	−0.0132 (15)	−0.0072 (15)
C30	0.079 (2)	0.073 (2)	0.097 (2)	0.0116 (17)	−0.0174 (18)	−0.0276 (18)
C31	0.0644 (19)	0.0577 (19)	0.082 (2)	0.0105 (16)	−0.0081 (17)	−0.0223 (16)
C32	0.091 (3)	0.079 (2)	0.094 (2)	0.005 (2)	−0.005 (2)	−0.011 (2)
C33	0.091 (3)	0.081 (3)	0.144 (4)	−0.015 (2)	0.018 (3)	−0.028 (3)
C34	0.076 (3)	0.107 (3)	0.153 (4)	0.000 (2)	−0.008 (3)	−0.077 (3)
C35	0.085 (3)	0.101 (3)	0.100 (3)	0.016 (2)	−0.023 (2)	−0.038 (2)
C36	0.081 (2)	0.072 (2)	0.087 (2)	0.0076 (18)	−0.0140 (18)	−0.0186 (17)
O1	0.0524 (10)	0.0543 (11)	0.0878 (13)	0.0077 (9)	−0.0182 (10)	−0.0081 (9)
O2	0.0871 (15)	0.0890 (16)	0.1244 (18)	0.0318 (12)	−0.0368 (13)	−0.0515 (14)
O3	0.0747 (13)	0.0691 (13)	0.0845 (14)	0.0159 (10)	−0.0314 (11)	−0.0211 (11)
O4	0.0724 (13)	0.0595 (12)	0.1057 (15)	0.0187 (10)	−0.0378 (11)	−0.0223 (11)
O5	0.0711 (13)	0.0715 (13)	0.0933 (14)	0.0202 (10)	−0.0288 (11)	−0.0291 (11)

C1—O3	1.352 (3)	C18—C19	1.370 (4)
C1—C2	1.374 (3)	C18—C23	1.371 (4)
C1—C6	1.427 (3)	C19—C20	1.380 (4)
C2—C3	1.388 (3)	C19—H19	0.9300
C2—H2	0.9300	C20—C21	1.351 (4)
C3—O4	1.368 (3)	C20—H20	0.9300
C3—C4	1.373 (3)	C21—C22	1.353 (4)
C4—C5	1.387 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.382 (4)
C5—O1	1.378 (3)	C22—H22	0.9300
C5—C6	1.382 (3)	C23—H23	0.9300
C6—C7	1.463 (3)	C24—C29	1.384 (3)
C7—O2	1.228 (3)	C24—C25	1.392 (3)
C7—C8	1.443 (4)	C25—C26	1.368 (3)
C8—C9	1.334 (3)	C25—H25	0.9300
C8—H8	0.9300	C26—C27	1.380 (3)
C9—O1	1.363 (3)	C26—H26	0.9300
C9—C24	1.466 (3)	C27—O5	1.375 (3)
C10—O3	1.424 (3)	C27—C28	1.388 (3)
C10—C11	1.501 (4)	C28—C29	1.375 (3)
C10—H10A	0.9700	C28—H28	0.9300
C10—H10B	0.9700	C29—H29	0.9300
C11—C12	1.370 (3)	C30—O5	1.430 (3)
C11—C16	1.379 (4)	C30—C31	1.492 (4)
C12—C13	1.387 (4)	C30—H30A	0.9700
C12—H12	0.9300	C30—H30B	0.9700
C13—C14	1.368 (4)	C31—C32	1.370 (4)
C13—H13	0.9300	C31—C36	1.376 (4)
C14—C15	1.368 (4)	C32—C33	1.378 (4)
C14—H14	0.9300	C32—H32	0.9300
C15—C16	1.368 (4)	C33—C34	1.372 (5)
C15—H15	0.9300	C33—H33	0.9300
C16—H16	0.9300	C34—C35	1.360 (5)
C17—O4	1.428 (3)	C34—H34	0.9300
C17—C18	1.505 (3)	C35—C36	1.380 (4)
C17—H17A	0.9700	C35—H35	0.9300
C17—H17B	0.9700	C36—H36	0.9300
O3—C1—C2	123.3 (2)	C18—C19—H19	119.7
O3—C1—C6	115.5 (2)	C20—C19—H19	119.7
C2—C1—C6	121.2 (3)	C21—C20—C19	120.2 (3)
C1—C2—C3	120.0 (3)	C21—C20—H20	119.9
C1—C2—H2	120.0	C19—C20—H20	119.9
C3—C2—H2	120.0	C20—C21—C22	120.2 (3)
O4—C3—C4	123.8 (3)	C20—C21—H21	119.9
O4—C3—C2	114.8 (2)	C22—C21—H21	119.9
C4—C3—C2	121.5 (2)	C21—C22—C23	119.9 (3)
C3—C4—C5	117.0 (3)	C21—C22—H22	120.0
C3—C4—H4	121.5	C23—C22—H22	120.0
C5—C4—H4	121.5	C18—C23—C22	120.7 (3)
O1—C5—C6	122.0 (2)	C18—C23—H23	119.6
O1—C5—C4	112.9 (2)	C22—C23—H23	119.6
C6—C5—C4	125.1 (2)	C29—C24—C25	117.4 (2)
C5—C6—C1	115.2 (2)	C29—C24—C9	121.0 (2)
C5—C6—C7	119.2 (2)	C25—C24—C9	121.6 (2)
C1—C6—C7	125.6 (3)	C26—C25—C24	121.4 (3)
O2—C7—C8	121.1 (2)	C26—C25—H25	119.3
O2—C7—C6	124.9 (3)	C24—C25—H25	119.3
C8—C7—C6	114.0 (3)	C25—C26—C27	120.3 (2)
C9—C8—C7	123.8 (2)	C25—C26—H26	119.9
C9—C8—H8	118.1	C27—C26—H26	119.9
C7—C8—H8	118.1	O5—C27—C26	116.3 (2)
C8—C9—O1	120.5 (2)	O5—C27—C28	124.3 (3)
C8—C9—C24	128.1 (2)	C26—C27—C28	119.4 (3)
O1—C9—C24	111.4 (2)	C29—C28—C27	119.4 (3)
O3—C10—C11	108.4 (2)	C29—C28—H28	120.3
O3—C10—H10A	110.0	C27—C28—H28	120.3
C11—C10—H10A	110.0	C28—C29—C24	121.9 (2)
O3—C10—H10B	110.0	C28—C29—H29	119.0
C11—C10—H10B	110.0	C24—C29—H29	119.0
H10A—C10—H10B	108.4	O5—C30—C31	109.2 (2)
C12—C11—C16	118.6 (3)	O5—C30—H30A	109.8
C12—C11—C10	122.9 (3)	C31—C30—H30A	109.8
C16—C11—C10	118.6 (3)	O5—C30—H30B	109.8
C11—C12—C13	120.2 (3)	C31—C30—H30B	109.8
C11—C12—H12	119.9	H30A—C30—H30B	108.3
C13—C12—H12	119.9	C32—C31—C36	118.9 (3)
C14—C13—C12	120.4 (3)	C32—C31—C30	120.2 (3)
C14—C13—H13	119.8	C36—C31—C30	120.9 (3)
C12—C13—H13	119.8	C31—C32—C33	121.2 (3)
C15—C14—C13	119.5 (3)	C31—C32—H32	119.4
C15—C14—H14	120.2	C33—C32—H32	119.4
C13—C14—H14	120.2	C34—C33—C32	119.3 (4)
C14—C15—C16	120.1 (3)	C34—C33—H33	120.3
C14—C15—H15	120.0	C32—C33—H33	120.3
C16—C15—H15	120.0	C35—C34—C33	120.1 (4)
C15—C16—C11	121.2 (3)	C35—C34—H34	120.0
C15—C16—H16	119.4	C33—C34—H34	120.0
C11—C16—H16	119.4	C34—C35—C36	120.5 (4)
O4—C17—C18	108.5 (2)	C34—C35—H35	119.8
O4—C17—H17A	110.0	C36—C35—H35	119.8
C18—C17—H17A	110.0	C31—C36—C35	120.1 (3)
O4—C17—H17B	110.0	C31—C36—H36	120.0
C18—C17—H17B	110.0	C35—C36—H36	120.0
H17A—C17—H17B	108.4	C9—O1—C5	120.0 (2)
C19—C18—C23	118.2 (3)	C1—O3—C10	118.6 (2)
C19—C18—C17	120.7 (3)	C3—O4—C17	117.2 (2)
C23—C18—C17	121.0 (3)	C27—O5—C30	117.8 (2)
C18—C19—C20	120.7 (3)