5,7-Dimeth-oxy-2-phenyl-4H-chromen-4-one.

The asymmetric unit of the title compound, C(17)H(14)O(4), contains two independent mol-ecules which differ in the relative orientations of the phenyl rings with repect to the essentially planar [maximum deviations of 0.029 (2) and 0.050 (2) Å in the two mol-ecules] chromene fused-ring system, forming dihedral angles of 10.3 (5) and 30.86 (5)° in the two mol-ecules. The crystal structure is stabilized by weak C-H⋯O and C--H⋯π inter-actions, and π-π stacking inter-actions.

Related literature

For the biological and pharmacological properties of benzopyrans and their derivatives, see Brooks (1998 ▶); Hatakeyama et al. (1988 ▶); Hyana & Saimoto (1987 ▶); Tang et al. (2007 ▶). For the importance of 4H-chromenes, see Liu et al. (2007 ▶); Wang, Fang et al. (2003 ▶); Wang, Zhang et al. (2003 ▶). For hydrogen bonding, see: Bernstein et al. (1995 ▶); Desiraju (1989 ▶); Desiraju & Steiner (1999 ▶); Etter (1990 ▶).

Experimental

Crystal data

C17H14O4

M = 282.28

Triclinic,

a = 7.3938 (17) Å

b = 11.430 (3) Å

c = 16.547 (4) Å

α = 92.414 (4)°

β = 102.723 (4)°

γ = 91.916 (4)°

V = 1361.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.35 × 0.32 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.977

15401 measured reflections

6096 independent reflections

3897 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.126

S = 1.01

6096 reflections

386 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003948/lh2766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003948/lh2766Isup2.hkl

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

C17H14O4	Z = 4
Mr = 282.28	F(000) = 592
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Melting point = 413–415 K
a = 7.3938 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.430 (3) Å	Cell parameters from 547 reflections
c = 16.547 (4) Å	θ = 2.7–27.0°
α = 92.414 (4)°	µ = 0.10 mm−1
β = 102.723 (4)°	T = 293 K
γ = 91.916 (4)°	Rectangular, colourless
V = 1361.5 (6) Å3	0.35 × 0.32 × 0.29 mm

Bruker SMART APEX CCD diffractometer	6096 independent reflections
Radiation source: fine-focus sealed tube	3897 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 0.3 pixels mm-1	θmax = 28.0°, θmin = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.967, Tmax = 0.977	l = −21→21
15401 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.201P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
6096 reflections	Δρmax = 0.17 e Å−3
386 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (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
O1A	0.84670 (17)	0.61660 (10)	0.25891 (7)	0.0474 (3)
C2A	0.7660 (2)	0.57055 (15)	0.18112 (10)	0.0424 (4)
C3A	0.7470 (3)	0.63612 (16)	0.11527 (11)	0.0511 (5)
H3A	0.6915	0.6014	0.0635	0.0716 (16)*
C4A	0.8077 (3)	0.75819 (17)	0.11977 (12)	0.0534 (5)
C5A	0.9527 (3)	0.92519 (15)	0.22512 (12)	0.0482 (4)
C6A	1.0295 (3)	0.96129 (16)	0.30639 (12)	0.0506 (5)
H6A	1.0710	1.0390	0.3193	0.0716 (16)*
C7A	1.0455 (3)	0.88267 (16)	0.36930 (11)	0.0471 (4)
C8A	0.9833 (2)	0.76767 (15)	0.35194 (11)	0.0459 (4)
H8A	0.9931	0.7148	0.3937	0.0716 (16)*
C9A	0.9053 (2)	0.73324 (14)	0.26986 (11)	0.0416 (4)
C10A	0.8873 (2)	0.80697 (15)	0.20411 (11)	0.0437 (4)
O11A	0.7924 (3)	0.81279 (13)	0.05644 (9)	0.0885 (6)
O12A	0.9347 (2)	0.99695 (11)	0.16087 (8)	0.0626 (4)
C13A	1.0217 (3)	1.11127 (17)	0.17698 (14)	0.0670 (6)
H13A	0.9654	1.1550	0.2150	0.0795 (19)*
H13B	1.0068	1.1507	0.1260	0.0795 (19)*
H13C	1.1515	1.1051	0.2008	0.0795 (19)*
O14A	1.1259 (2)	0.92860 (11)	0.44691 (8)	0.0607 (4)
C15A	1.1399 (3)	0.85301 (18)	0.51405 (12)	0.0651 (6)
H15A	1.0180	0.8247	0.5172	0.0795 (19)*
H15B	1.1978	0.8955	0.5650	0.0795 (19)*
H15C	1.2131	0.7879	0.5052	0.0795 (19)*
C16A	0.7055 (2)	0.44676 (15)	0.18240 (10)	0.0419 (4)
C17A	0.7040 (3)	0.39431 (16)	0.25611 (11)	0.0525 (5)
H17A	0.7461	0.4370	0.3062	0.0716 (16)*
C18A	0.6406 (3)	0.27909 (17)	0.25620 (13)	0.0596 (5)
H18A	0.6410	0.2451	0.3063	0.0716 (16)*
C19A	0.5772 (3)	0.21453 (17)	0.18291 (13)	0.0583 (5)
H19A	0.5341	0.1372	0.1832	0.0716 (16)*
C20A	0.5780 (3)	0.26564 (17)	0.10883 (13)	0.0591 (5)
H20A	0.5342	0.2227	0.0589	0.0716 (16)*
C21A	0.6430 (3)	0.37968 (16)	0.10844 (11)	0.0521 (5)
H21A	0.6455	0.4125	0.0582	0.0716 (16)*
O1B	0.47575 (17)	0.66672 (10)	0.35030 (7)	0.0481 (3)
C2B	0.5506 (2)	0.75030 (15)	0.41057 (10)	0.0430 (4)
C3B	0.5514 (3)	0.86351 (16)	0.39514 (11)	0.0482 (4)
H3B	0.5994	0.9175	0.4389	0.0716 (16)*
C4B	0.4812 (2)	0.90719 (15)	0.31364 (11)	0.0458 (4)
C5B	0.3403 (2)	0.83268 (15)	0.16260 (11)	0.0432 (4)
C6B	0.2695 (3)	0.73982 (16)	0.10767 (11)	0.0474 (4)
H6B	0.2246	0.7531	0.0519	0.0716 (16)*
C7B	0.2645 (2)	0.62654 (15)	0.13467 (10)	0.0439 (4)
C8B	0.3323 (2)	0.60447 (15)	0.21647 (10)	0.0425 (4)
H8B	0.3293	0.5289	0.2350	0.0716 (16)*
C9B	0.4054 (2)	0.69884 (15)	0.27057 (10)	0.0397 (4)
C10B	0.4104 (2)	0.81474 (14)	0.24840 (10)	0.0407 (4)
O11B	0.4835 (2)	1.01305 (11)	0.30281 (8)	0.0661 (4)
O12B	0.34727 (19)	0.94462 (10)	0.13977 (8)	0.0578 (4)
C13B	0.2722 (4)	0.96692 (18)	0.05480 (12)	0.0726 (7)
H13D	0.3437	0.9288	0.0204	0.0795 (19)*
H13E	0.2766	1.0498	0.0478	0.0795 (19)*
H13F	0.1457	0.9371	0.0392	0.0795 (19)*
O14B	0.19111 (19)	0.54206 (11)	0.07452 (7)	0.0582 (4)
C15B	0.1540 (3)	0.42788 (16)	0.09996 (12)	0.0571 (5)
H15D	0.2679	0.3959	0.1280	0.0795 (19)*
H15E	0.0984	0.3781	0.0521	0.0795 (19)*
H15F	0.0705	0.4326	0.1369	0.0795 (19)*
C16B	0.6345 (2)	0.69686 (16)	0.48880 (11)	0.0477 (4)
C17B	0.7041 (3)	0.5870 (2)	0.48775 (13)	0.0708 (6)
H17B	0.6916	0.5444	0.4375	0.0716 (16)*
C18B	0.7922 (4)	0.5393 (2)	0.56032 (16)	0.0905 (8)
H18B	0.8401	0.4653	0.5584	0.0716 (16)*
C19B	0.8101 (4)	0.5986 (3)	0.63429 (16)	0.0886 (9)
H19B	0.8713	0.5662	0.6829	0.0716 (16)*
C20B	0.7371 (4)	0.7066 (3)	0.63683 (13)	0.0845 (8)
H20B	0.7460	0.7467	0.6877	0.0716 (16)*
C21B	0.6504 (3)	0.7572 (2)	0.56492 (12)	0.0640 (6)
H21B	0.6029	0.8313	0.5674	0.0716 (16)*

	U11	U22	U33	U12	U13	U23
O1A	0.0561 (8)	0.0411 (7)	0.0418 (7)	−0.0064 (6)	0.0050 (6)	0.0036 (5)
C2A	0.0397 (10)	0.0445 (10)	0.0415 (9)	−0.0022 (8)	0.0068 (8)	0.0014 (8)
C3A	0.0570 (12)	0.0483 (11)	0.0431 (10)	−0.0088 (9)	0.0020 (9)	0.0040 (8)
C4A	0.0564 (12)	0.0493 (11)	0.0490 (11)	−0.0052 (9)	−0.0011 (9)	0.0123 (9)
C5A	0.0462 (11)	0.0412 (10)	0.0572 (11)	0.0008 (8)	0.0108 (9)	0.0066 (9)
C6A	0.0551 (12)	0.0382 (10)	0.0579 (12)	−0.0019 (8)	0.0131 (9)	−0.0017 (9)
C7A	0.0470 (11)	0.0482 (11)	0.0463 (10)	0.0001 (8)	0.0125 (8)	−0.0051 (8)
C8A	0.0487 (11)	0.0457 (11)	0.0431 (10)	0.0013 (8)	0.0098 (8)	0.0023 (8)
C9A	0.0395 (10)	0.0369 (10)	0.0479 (10)	−0.0021 (7)	0.0094 (8)	0.0004 (8)
C10A	0.0410 (10)	0.0407 (10)	0.0475 (10)	−0.0014 (8)	0.0056 (8)	0.0041 (8)
O11A	0.1298 (15)	0.0642 (10)	0.0536 (9)	−0.0281 (9)	−0.0169 (9)	0.0215 (8)
O12A	0.0768 (10)	0.0429 (8)	0.0616 (8)	−0.0094 (7)	0.0014 (7)	0.0124 (6)
C13A	0.0828 (16)	0.0411 (11)	0.0732 (14)	−0.0029 (11)	0.0086 (12)	0.0073 (10)
O14A	0.0793 (10)	0.0523 (8)	0.0473 (8)	−0.0068 (7)	0.0104 (7)	−0.0076 (6)
C15A	0.0802 (16)	0.0634 (14)	0.0472 (11)	−0.0097 (11)	0.0077 (10)	−0.0046 (10)
C16A	0.0382 (10)	0.0424 (10)	0.0455 (10)	0.0002 (8)	0.0103 (8)	0.0033 (8)
C17A	0.0615 (13)	0.0478 (11)	0.0468 (10)	−0.0043 (9)	0.0101 (9)	0.0012 (9)
C18A	0.0715 (14)	0.0504 (12)	0.0575 (12)	−0.0033 (10)	0.0150 (11)	0.0125 (10)
C19A	0.0613 (13)	0.0415 (11)	0.0712 (14)	−0.0060 (9)	0.0139 (11)	0.0045 (10)
C20A	0.0670 (14)	0.0486 (12)	0.0583 (12)	−0.0090 (10)	0.0103 (10)	−0.0081 (10)
C21A	0.0586 (12)	0.0505 (11)	0.0458 (10)	−0.0063 (9)	0.0098 (9)	0.0015 (9)
O1B	0.0634 (8)	0.0400 (7)	0.0363 (6)	0.0004 (6)	0.0005 (6)	0.0056 (5)
C2B	0.0442 (10)	0.0437 (10)	0.0389 (9)	0.0000 (8)	0.0052 (8)	−0.0002 (8)
C3B	0.0537 (12)	0.0429 (11)	0.0447 (10)	−0.0017 (8)	0.0052 (9)	−0.0014 (8)
C4B	0.0467 (11)	0.0385 (10)	0.0503 (10)	−0.0006 (8)	0.0070 (8)	0.0032 (8)
C5B	0.0458 (10)	0.0379 (10)	0.0458 (10)	0.0026 (8)	0.0086 (8)	0.0094 (8)
C6B	0.0551 (11)	0.0485 (11)	0.0368 (9)	0.0023 (9)	0.0054 (8)	0.0084 (8)
C7B	0.0466 (11)	0.0438 (10)	0.0400 (9)	0.0000 (8)	0.0070 (8)	0.0013 (8)
C8B	0.0485 (11)	0.0359 (9)	0.0427 (10)	0.0003 (8)	0.0091 (8)	0.0054 (7)
C9B	0.0419 (10)	0.0410 (10)	0.0357 (9)	0.0024 (7)	0.0066 (7)	0.0059 (7)
C10B	0.0402 (10)	0.0387 (9)	0.0419 (9)	0.0030 (7)	0.0057 (8)	0.0055 (7)
O11B	0.0908 (11)	0.0367 (8)	0.0641 (9)	−0.0052 (7)	0.0034 (8)	0.0062 (6)
O12B	0.0784 (10)	0.0411 (7)	0.0495 (7)	0.0003 (6)	0.0023 (7)	0.0152 (6)
C13B	0.112 (2)	0.0524 (13)	0.0505 (12)	0.0059 (12)	0.0084 (12)	0.0219 (10)
O14B	0.0795 (10)	0.0478 (8)	0.0414 (7)	−0.0099 (7)	0.0034 (6)	−0.0021 (6)
C15B	0.0674 (14)	0.0449 (11)	0.0562 (12)	−0.0079 (9)	0.0101 (10)	−0.0039 (9)
C16B	0.0450 (11)	0.0562 (12)	0.0401 (10)	−0.0037 (9)	0.0058 (8)	0.0066 (8)
C17B	0.0904 (17)	0.0693 (15)	0.0514 (12)	0.0209 (12)	0.0086 (11)	0.0136 (11)
C18B	0.104 (2)	0.0924 (19)	0.0740 (17)	0.0314 (16)	0.0065 (15)	0.0352 (15)
C19B	0.0694 (17)	0.131 (3)	0.0593 (15)	−0.0098 (16)	−0.0052 (12)	0.0459 (17)
C20B	0.0812 (18)	0.126 (2)	0.0370 (11)	−0.0270 (17)	−0.0028 (11)	0.0029 (13)
C21B	0.0662 (14)	0.0742 (15)	0.0465 (11)	−0.0095 (11)	0.0047 (10)	−0.0034 (10)

O1A—C2A	1.369 (2)	O1B—C2B	1.362 (2)
O1A—C9A	1.380 (2)	O1B—C9B	1.3773 (19)
C2A—C3A	1.333 (2)	C2B—C3B	1.329 (2)
C2A—C16A	1.472 (2)	C2B—C16B	1.474 (2)
C3A—C4A	1.445 (3)	C3B—C4B	1.450 (2)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—O11A	1.228 (2)	C4B—O11B	1.231 (2)
C4A—C10A	1.468 (3)	C4B—C10B	1.474 (2)
C5A—O12A	1.356 (2)	C5B—O12B	1.3517 (19)
C5A—C6A	1.379 (3)	C5B—C6B	1.378 (2)
C5A—C10A	1.422 (2)	C5B—C10B	1.426 (2)
C6A—C7A	1.392 (2)	C6B—C7B	1.389 (2)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—O14A	1.365 (2)	C7B—O14B	1.365 (2)
C7A—C8A	1.375 (2)	C7B—C8B	1.373 (2)
C8A—C9A	1.388 (2)	C8B—C9B	1.387 (2)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.390 (2)	C9B—C10B	1.391 (2)
O12A—C13A	1.425 (2)	O12B—C13B	1.430 (2)
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
O14A—C15A	1.424 (2)	O14B—C15B	1.425 (2)
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C16A—C17A	1.384 (2)	C16B—C17B	1.374 (3)
C16A—C21A	1.395 (2)	C16B—C21B	1.390 (3)
C17A—C18A	1.383 (3)	C17B—C18B	1.378 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.373 (3)	C18B—C19B	1.352 (4)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.381 (3)	C19B—C20B	1.366 (4)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.375 (3)	C20B—C21B	1.381 (3)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—H21A	0.9300	C21B—H21B	0.9300
C2A—O1A—C9A	119.71 (13)	C2B—O1B—C9B	119.73 (13)
C3A—C2A—O1A	120.94 (16)	C3B—C2B—O1B	121.51 (15)
C3A—C2A—C16A	127.26 (16)	C3B—C2B—C16B	127.33 (16)
O1A—C2A—C16A	111.79 (14)	O1B—C2B—C16B	111.08 (15)
C2A—C3A—C4A	123.68 (17)	C2B—C3B—C4B	123.40 (17)
C2A—C3A—H3A	118.2	C2B—C3B—H3B	118.3
C4A—C3A—H3A	118.2	C4B—C3B—H3B	118.3
O11A—C4A—C3A	120.59 (18)	O11B—C4B—C3B	120.83 (16)
O11A—C4A—C10A	124.93 (17)	O11B—C4B—C10B	125.04 (16)
C3A—C4A—C10A	114.47 (16)	C3B—C4B—C10B	114.12 (15)
O12A—C5A—C6A	123.64 (16)	O12B—C5B—C6B	123.15 (15)
O12A—C5A—C10A	115.79 (16)	O12B—C5B—C10B	116.05 (15)
C6A—C5A—C10A	120.57 (17)	C6B—C5B—C10B	120.80 (15)
C5A—C6A—C7A	120.67 (17)	C5B—C6B—C7B	120.73 (16)
C5A—C6A—H6A	119.7	C5B—C6B—H6B	119.6
C7A—C6A—H6A	119.7	C7B—C6B—H6B	119.6
O14A—C7A—C8A	124.12 (17)	O14B—C7B—C8B	123.99 (16)
O14A—C7A—C6A	115.13 (16)	O14B—C7B—C6B	115.29 (15)
C8A—C7A—C6A	120.76 (17)	C8B—C7B—C6B	120.71 (16)
C7A—C8A—C9A	117.70 (16)	C7B—C8B—C9B	117.70 (16)
C7A—C8A—H8A	121.2	C7B—C8B—H8B	121.1
C9A—C8A—H8A	121.2	C9B—C8B—H8B	121.1
O1A—C9A—C8A	113.28 (15)	O1B—C9B—C8B	113.06 (14)
O1A—C9A—C10A	122.35 (15)	O1B—C9B—C10B	122.23 (15)
C8A—C9A—C10A	124.36 (16)	C8B—C9B—C10B	124.70 (15)
C9A—C10A—C5A	115.92 (16)	C9B—C10B—C5B	115.31 (15)
C9A—C10A—C4A	118.78 (16)	C9B—C10B—C4B	118.81 (15)
C5A—C10A—C4A	125.28 (16)	C5B—C10B—C4B	125.86 (15)
C5A—O12A—C13A	117.71 (15)	C5B—O12B—C13B	117.79 (14)
O12A—C13A—H13A	109.5	O12B—C13B—H13D	109.5
O12A—C13A—H13B	109.5	O12B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
O12A—C13A—H13C	109.5	O12B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C7A—O14A—C15A	117.48 (15)	C7B—O14B—C15B	117.91 (13)
O14A—C15A—H15A	109.5	O14B—C15B—H15D	109.5
O14A—C15A—H15B	109.5	O14B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O14A—C15A—H15C	109.5	O14B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C17A—C16A—C21A	118.04 (16)	C17B—C16B—C21B	118.44 (18)
C17A—C16A—C2A	121.46 (16)	C17B—C16B—C2B	120.39 (17)
C21A—C16A—C2A	120.47 (15)	C21B—C16B—C2B	121.14 (18)
C18A—C17A—C16A	120.81 (18)	C16B—C17B—C18B	120.7 (2)
C18A—C17A—H17A	119.6	C16B—C17B—H17B	119.7
C16A—C17A—H17A	119.6	C18B—C17B—H17B	119.7
C19A—C18A—C17A	120.55 (18)	C19B—C18B—C17B	120.9 (3)
C19A—C18A—H18A	119.7	C19B—C18B—H18B	119.5
C17A—C18A—H18A	119.7	C17B—C18B—H18B	119.5
C18A—C19A—C20A	119.32 (18)	C18B—C19B—C20B	119.3 (2)
C18A—C19A—H19A	120.3	C18B—C19B—H19B	120.4
C20A—C19A—H19A	120.3	C20B—C19B—H19B	120.4
C21A—C20A—C19A	120.36 (18)	C19B—C20B—C21B	121.0 (2)
C21A—C20A—H20A	119.8	C19B—C20B—H20B	119.5
C19A—C20A—H20A	119.8	C21B—C20B—H20B	119.5
C20A—C21A—C16A	120.90 (17)	C20B—C21B—C16B	119.7 (2)
C20A—C21A—H21A	119.5	C20B—C21B—H21B	120.2
C16A—C21A—H21A	119.5	C16B—C21B—H21B	120.2
C9A—O1A—C2A—C3A	1.6 (2)	C9B—O1B—C2B—C3B	2.6 (2)
C9A—O1A—C2A—C16A	−177.46 (14)	C9B—O1B—C2B—C16B	−174.21 (14)
O1A—C2A—C3A—C4A	−0.1 (3)	O1B—C2B—C3B—C4B	−2.6 (3)
C16A—C2A—C3A—C4A	178.82 (18)	C16B—C2B—C3B—C4B	173.59 (17)
C2A—C3A—C4A—O11A	177.3 (2)	C2B—C3B—C4B—O11B	179.30 (18)
C2A—C3A—C4A—C10A	−2.1 (3)	C2B—C3B—C4B—C10B	−0.8 (3)
O12A—C5A—C6A—C7A	−179.36 (17)	O12B—C5B—C6B—C7B	−179.50 (16)
C10A—C5A—C6A—C7A	0.4 (3)	C10B—C5B—C6B—C7B	0.1 (3)
C5A—C6A—C7A—O14A	179.18 (16)	C5B—C6B—C7B—O14B	179.95 (16)
C5A—C6A—C7A—C8A	−0.7 (3)	C5B—C6B—C7B—C8B	−0.9 (3)
O14A—C7A—C8A—C9A	−179.62 (16)	O14B—C7B—C8B—C9B	179.06 (16)
C6A—C7A—C8A—C9A	0.3 (3)	C6B—C7B—C8B—C9B	0.0 (3)
C2A—O1A—C9A—C8A	179.66 (14)	C2B—O1B—C9B—C8B	−179.34 (15)
C2A—O1A—C9A—C10A	−0.7 (2)	C2B—O1B—C9B—C10B	1.1 (2)
C7A—C8A—C9A—O1A	−179.81 (15)	C7B—C8B—C9B—O1B	−177.72 (15)
C7A—C8A—C9A—C10A	0.6 (3)	C7B—C8B—C9B—C10B	1.8 (3)
O1A—C9A—C10A—C5A	179.54 (15)	O1B—C9B—C10B—C5B	176.98 (15)
C8A—C9A—C10A—C5A	−0.9 (3)	C8B—C9B—C10B—C5B	−2.5 (3)
O1A—C9A—C10A—C4A	−1.6 (3)	O1B—C9B—C10B—C4B	−4.5 (2)
C8A—C9A—C10A—C4A	177.98 (16)	C8B—C9B—C10B—C4B	176.01 (16)
O12A—C5A—C10A—C9A	−179.87 (15)	O12B—C5B—C10B—C9B	−178.86 (15)
C6A—C5A—C10A—C9A	0.4 (3)	C6B—C5B—C10B—C9B	1.5 (2)
O12A—C5A—C10A—C4A	1.4 (3)	O12B—C5B—C10B—C4B	2.7 (3)
C6A—C5A—C10A—C4A	−178.39 (17)	C6B—C5B—C10B—C4B	−176.92 (17)
O11A—C4A—C10A—C9A	−176.5 (2)	O11B—C4B—C10B—C9B	−175.93 (17)
C3A—C4A—C10A—C9A	2.9 (3)	C3B—C4B—C10B—C9B	4.1 (2)
O11A—C4A—C10A—C5A	2.2 (3)	O11B—C4B—C10B—C5B	2.5 (3)
C3A—C4A—C10A—C5A	−178.40 (17)	C3B—C4B—C10B—C5B	−177.47 (16)
C6A—C5A—O12A—C13A	8.5 (3)	C6B—C5B—O12B—C13B	1.8 (3)
C10A—C5A—O12A—C13A	−171.26 (17)	C10B—C5B—O12B—C13B	−177.77 (17)
C8A—C7A—O14A—C15A	−2.3 (3)	C8B—C7B—O14B—C15B	11.0 (3)
C6A—C7A—O14A—C15A	177.86 (17)	C6B—C7B—O14B—C15B	−169.90 (16)
C3A—C2A—C16A—C17A	−168.56 (19)	C3B—C2B—C16B—C17B	−148.0 (2)
O1A—C2A—C16A—C17A	10.4 (2)	O1B—C2B—C16B—C17B	28.5 (3)
C3A—C2A—C16A—C21A	9.7 (3)	C3B—C2B—C16B—C21B	30.0 (3)
O1A—C2A—C16A—C21A	−171.29 (15)	O1B—C2B—C16B—C21B	−153.46 (17)
C21A—C16A—C17A—C18A	−0.6 (3)	C21B—C16B—C17B—C18B	−1.8 (3)
C2A—C16A—C17A—C18A	177.72 (17)	C2B—C16B—C17B—C18B	176.3 (2)
C16A—C17A—C18A—C19A	−0.3 (3)	C16B—C17B—C18B—C19B	0.9 (4)
C17A—C18A—C19A—C20A	0.3 (3)	C17B—C18B—C19B—C20B	0.9 (4)
C18A—C19A—C20A—C21A	0.5 (3)	C18B—C19B—C20B—C21B	−1.8 (4)
C19A—C20A—C21A—C16A	−1.5 (3)	C19B—C20B—C21B—C16B	0.9 (4)
C17A—C16A—C21A—C20A	1.5 (3)	C17B—C16B—C21B—C20B	0.9 (3)
C2A—C16A—C21A—C20A	−176.89 (17)	C2B—C16B—C21B—C20B	−177.16 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C17A—H17A···O1A	0.93	2.38	2.713 (2)	101
C13B—H13E···O11Ai	0.96	2.37	3.169 (2)	141
C19A—H19A···O11Bii	0.93	2.57	3.256 (2)	131
C19A—H19A···O12Bii	0.93	2.55	3.442 (2)	161
C13A—H13A···Cg5iii	0.96	3.14	3.838	131
C15A—H15A···Cg6	0.96	3.16	4.059	156
C15B—H15D···Cg5	0.96	2.85	3.786	166

		Cg···Cg	α	perp
Cg1	Cg2	3.972 (1)	10.88	3.575
Cg1	Cg4	3.646 (1)	8.06	3.578
Cg1	Cg4i	3.785 (1)	8.06	3.535
Cg2	Cg3i	3.792 (1)	9.89	3.599
Cg2	Cg3	3.883 (1)	9.89	3.743
Cg3	Cg4i	3.769 (1)	7.07	3.516

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17A—H17A⋯O1A	0.93	2.38	2.713 (2)	101
C13B—H13E⋯O11Ai	0.96	2.37	3.169 (2)	141
C19A—H19A⋯O11Bii	0.93	2.57	3.256 (2)	131
C19A—H19A⋯O12Bii	0.93	2.55	3.442 (2)	161
C15B—H15D⋯Cg5	0.96	2.85	3.786	166

Symmetry codes: (i) ; (ii) . Cg5 is the centroids of the C16A–C21A ring.

Table 2

π–π Stacking interactions (Å, °)

Cgi	Cgj	Cgi⋯Cgj	α	perp
Cg1	Cg2	3.972 (1)	10.9	3.575
Cg1	Cg4	3.646 (1)	8.1	3.578
Cg1	Cg4i	3.785 (1)	8.1	3.535
Cg2	Cg3i	3.792 (1)	9.9	3.599
Cg2	Cg3	3.883 (1)	9.9	3.743
Cg3	Cg4i	3.769 (1)	7.1	3.516

Symmetry code: (i) . Cg1, Cg2, Cg3, and Cg4 are the centroids of the O1A/C2A–C4A/C9A/C10A, O1B/C2B–C4B/C9B/C10B, C5A–C10A and C5B–C10B rings, respectively. α is the dihedral angle between ring planes and perp is the perpendicular distance between ring planes.