1-(2-Naphth-yl)-3-phenyl-prop-2-en-1-one.

The title compound, C(19)H(14)O, contains two independent mol-ecules with the same s-cis conformation for the ketone unit. Both mol-ecules are non-planar with dihedral angles of 51.9 (1) and 48.0 (1)° between the benzene ring and the naphthalene ring system. In the crystal, neighboring mol-ecules are stabilized by intermolecular C-H⋯π inter-actions, giving a two-dimensional supra-molecular array parallel to the ab plane.

Related literature

For background to chalcone and its derivatives, see: Agrinskaya et al. (1999 ▶); Indira et al. (2002 ▶); Opletalova (2000 ▶); Pandey et al. (2005 ▶). For related structures, see: Moorthi et al. (2005 ▶); Tang et al. (2008 ▶).

Experimental

Crystal data

C19H14O

M = 258.30

Triclinic,

a = 9.5878 (8) Å

b = 9.6111 (8) Å

c = 15.5358 (13) Å

α = 98.746 (2)°

β = 91.222 (2)°

γ = 105.764 (1)°

V = 1358.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.982

10623 measured reflections

5271 independent reflections

3483 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.174

S = 1.03

5271 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025483/at2828sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025483/at2828Isup2.hkl

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

C19H14O	Z = 4
Mr = 258.30	F(000) = 544
Triclinic, P1	Dx = 1.263 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5878 (8) Å	Cell parameters from 2584 reflections
b = 9.6111 (8) Å	θ = 2.2–26.9°
c = 15.5358 (13) Å	µ = 0.08 mm−1
α = 98.746 (2)°	T = 295 K
β = 91.222 (2)°	Block, colourless
γ = 105.764 (1)°	0.30 × 0.28 × 0.20 mm
V = 1358.8 (2) Å3

Bruker SMART APEX area-detector diffractometer	5271 independent reflections
Radiation source: fine-focus sealed tube	3483 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.972, Tmax = 0.982	k = −11→11
10623 measured reflections	l = −16→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0943P)2 + 0.07P] where P = (Fo2 + 2Fc2)/3
5271 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.55561 (16)	0.34700 (16)	0.30964 (10)	0.0513 (4)
H1	0.6529	0.3967	0.3072	0.062*
C2	0.50388 (16)	0.31927 (16)	0.38862 (10)	0.0512 (4)
C3	0.35522 (17)	0.24451 (16)	0.39193 (11)	0.0564 (4)
H3	0.3193	0.2228	0.4449	0.068*
C4	0.26443 (17)	0.20422 (17)	0.31847 (11)	0.0569 (4)
H4	0.1666	0.1581	0.3224	0.068*
C5	0.31541 (16)	0.23088 (15)	0.23681 (10)	0.0492 (4)
C6	0.22432 (18)	0.18909 (17)	0.15896 (12)	0.0617 (4)
H6	0.1260	0.1428	0.1611	0.074*
C7	0.2783 (2)	0.2156 (2)	0.08125 (12)	0.0730 (5)
H7	0.2168	0.1879	0.0308	0.088*
C8	0.4258 (2)	0.2841 (2)	0.07654 (12)	0.0735 (5)
H8	0.4618	0.3014	0.0229	0.088*
C9	0.51710 (19)	0.32576 (18)	0.14943 (11)	0.0634 (5)
H9	0.6152	0.3705	0.1451	0.076*
C10	0.46492 (16)	0.30194 (15)	0.23190 (10)	0.0493 (4)
C11	0.60363 (17)	0.37413 (17)	0.46910 (11)	0.0556 (4)
C12	0.57387 (18)	0.29557 (18)	0.54382 (11)	0.0598 (4)
H12	0.5089	0.2024	0.5359	0.072*
C13	0.63803 (17)	0.35515 (17)	0.62227 (11)	0.0548 (4)
H13	0.6999	0.4496	0.6276	0.066*
C14	0.62209 (15)	0.28857 (16)	0.70127 (11)	0.0510 (4)
C15	0.67187 (17)	0.37583 (18)	0.78179 (11)	0.0581 (4)
H15	0.7170	0.4753	0.7845	0.070*
C16	0.65513 (19)	0.3166 (2)	0.85796 (12)	0.0693 (5)
H16	0.6880	0.3765	0.9114	0.083*
C17	0.59008 (19)	0.1694 (2)	0.85492 (13)	0.0728 (5)
H17	0.5791	0.1297	0.9062	0.087*
C18	0.54137 (18)	0.08120 (19)	0.77577 (13)	0.0678 (5)
H18	0.4979	−0.0184	0.7737	0.081*
C19	0.55654 (17)	0.13930 (17)	0.69964 (12)	0.0596 (4)
H19	0.5228	0.0785	0.6466	0.071*
C20	0.17274 (16)	0.87506 (16)	0.70822 (10)	0.0511 (4)
H20	0.2253	0.9728	0.7122	0.061*
C21	0.11862 (16)	0.79474 (16)	0.62779 (10)	0.0522 (4)
C22	0.03921 (17)	0.64537 (17)	0.62222 (11)	0.0590 (4)
H22	0.0000	0.5909	0.5682	0.071*
C23	0.01976 (17)	0.58105 (17)	0.69474 (11)	0.0592 (4)
H23	−0.0299	0.4822	0.6894	0.071*
C24	0.07335 (16)	0.66125 (16)	0.77786 (11)	0.0509 (4)
C25	0.05131 (18)	0.59894 (18)	0.85505 (12)	0.0639 (5)
H25	0.0025	0.5001	0.8513	0.077*
C26	0.10026 (19)	0.6810 (2)	0.93437 (12)	0.0701 (5)
H26	0.0844	0.6380	0.9843	0.084*
C27	0.17445 (19)	0.8298 (2)	0.94162 (12)	0.0675 (5)
H27	0.2066	0.8853	0.9964	0.081*
C28	0.19983 (17)	0.89384 (17)	0.86894 (11)	0.0584 (4)
H28	0.2505	0.9925	0.8745	0.070*
C29	0.15019 (15)	0.81224 (16)	0.78502 (10)	0.0489 (4)
C30	0.14645 (18)	0.86629 (18)	0.54882 (11)	0.0586 (4)
C31	0.04008 (18)	0.80888 (19)	0.47213 (11)	0.0641 (5)
H31	−0.0495	0.7444	0.4786	0.077*
C32	0.06982 (18)	0.84735 (17)	0.39480 (11)	0.0570 (4)
H32	0.1619	0.9090	0.3907	0.068*
C33	−0.02592 (17)	0.80371 (16)	0.31523 (10)	0.0519 (4)
C34	0.03151 (18)	0.83379 (17)	0.23635 (11)	0.0590 (4)
H34	0.1296	0.8816	0.2351	0.071*
C35	−0.0556 (2)	0.79344 (19)	0.16030 (12)	0.0668 (5)
H35	−0.0160	0.8138	0.1080	0.080*
C36	−0.2010 (2)	0.72311 (18)	0.16094 (12)	0.0664 (5)
H36	−0.2594	0.6956	0.1092	0.080*
C37	−0.25980 (18)	0.69361 (17)	0.23827 (12)	0.0628 (5)
H37	−0.3582	0.6465	0.2388	0.075*
C38	−0.17429 (17)	0.73317 (17)	0.31472 (11)	0.0581 (4)
H38	−0.2153	0.7129	0.3667	0.070*
O1	0.70779 (13)	0.48236 (13)	0.47157 (8)	0.0757 (4)
O2	0.25405 (14)	0.96832 (14)	0.54733 (8)	0.0820 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0439 (8)	0.0479 (8)	0.0599 (10)	0.0099 (6)	0.0067 (7)	0.0072 (7)
C2	0.0504 (9)	0.0477 (8)	0.0545 (9)	0.0131 (7)	0.0059 (7)	0.0058 (7)
C3	0.0554 (9)	0.0568 (9)	0.0559 (10)	0.0126 (7)	0.0119 (8)	0.0105 (7)
C4	0.0468 (9)	0.0538 (9)	0.0677 (11)	0.0100 (7)	0.0082 (8)	0.0096 (8)
C5	0.0478 (8)	0.0433 (8)	0.0577 (10)	0.0160 (6)	0.0038 (7)	0.0060 (7)
C6	0.0529 (9)	0.0570 (9)	0.0723 (12)	0.0134 (7)	−0.0040 (8)	0.0059 (8)
C7	0.0762 (13)	0.0800 (12)	0.0596 (11)	0.0207 (10)	−0.0071 (9)	0.0047 (9)
C8	0.0792 (13)	0.0863 (13)	0.0551 (11)	0.0230 (10)	0.0082 (9)	0.0115 (9)
C9	0.0600 (10)	0.0676 (10)	0.0620 (11)	0.0160 (8)	0.0134 (8)	0.0114 (8)
C10	0.0498 (9)	0.0432 (8)	0.0561 (9)	0.0150 (6)	0.0063 (7)	0.0071 (7)
C11	0.0532 (9)	0.0548 (9)	0.0561 (10)	0.0129 (7)	0.0074 (7)	0.0042 (7)
C12	0.0585 (10)	0.0542 (9)	0.0621 (11)	0.0101 (7)	−0.0001 (8)	0.0062 (8)
C13	0.0482 (9)	0.0516 (9)	0.0629 (10)	0.0111 (7)	0.0015 (7)	0.0095 (7)
C14	0.0414 (8)	0.0522 (9)	0.0596 (10)	0.0134 (7)	0.0013 (7)	0.0090 (7)
C15	0.0518 (9)	0.0571 (9)	0.0629 (11)	0.0118 (7)	−0.0012 (8)	0.0091 (8)
C16	0.0642 (11)	0.0820 (13)	0.0599 (11)	0.0181 (9)	−0.0020 (8)	0.0110 (9)
C17	0.0624 (11)	0.0871 (13)	0.0783 (13)	0.0238 (10)	0.0067 (10)	0.0364 (11)
C18	0.0545 (10)	0.0579 (10)	0.0948 (14)	0.0149 (8)	0.0027 (9)	0.0262 (10)
C19	0.0514 (9)	0.0541 (9)	0.0727 (11)	0.0144 (7)	−0.0026 (8)	0.0101 (8)
C20	0.0449 (8)	0.0442 (8)	0.0612 (10)	0.0084 (6)	0.0009 (7)	0.0064 (7)
C21	0.0451 (8)	0.0546 (9)	0.0555 (10)	0.0136 (7)	0.0012 (7)	0.0053 (7)
C22	0.0555 (9)	0.0529 (9)	0.0624 (10)	0.0122 (7)	−0.0045 (8)	−0.0034 (8)
C23	0.0537 (9)	0.0454 (8)	0.0747 (12)	0.0110 (7)	−0.0006 (8)	0.0045 (8)
C24	0.0418 (8)	0.0465 (8)	0.0653 (10)	0.0139 (6)	0.0016 (7)	0.0095 (7)
C25	0.0592 (10)	0.0544 (9)	0.0807 (12)	0.0146 (8)	0.0026 (9)	0.0219 (9)
C26	0.0708 (12)	0.0732 (12)	0.0702 (12)	0.0192 (9)	0.0039 (9)	0.0255 (10)
C27	0.0689 (11)	0.0751 (12)	0.0568 (10)	0.0190 (9)	−0.0034 (8)	0.0085 (9)
C28	0.0585 (10)	0.0523 (9)	0.0604 (10)	0.0119 (7)	−0.0016 (8)	0.0050 (8)
C29	0.0418 (8)	0.0480 (8)	0.0563 (10)	0.0128 (6)	0.0008 (7)	0.0063 (7)
C30	0.0520 (9)	0.0614 (10)	0.0574 (10)	0.0104 (8)	0.0046 (7)	0.0045 (8)
C31	0.0550 (10)	0.0697 (11)	0.0607 (11)	0.0064 (8)	0.0034 (8)	0.0100 (8)
C32	0.0531 (9)	0.0526 (9)	0.0617 (11)	0.0094 (7)	0.0045 (8)	0.0084 (8)
C33	0.0511 (9)	0.0452 (8)	0.0593 (10)	0.0124 (7)	0.0021 (7)	0.0105 (7)
C34	0.0554 (9)	0.0561 (9)	0.0659 (11)	0.0124 (7)	0.0100 (8)	0.0159 (8)
C35	0.0761 (12)	0.0660 (11)	0.0601 (11)	0.0196 (9)	0.0090 (9)	0.0154 (8)
C36	0.0708 (12)	0.0614 (10)	0.0661 (11)	0.0182 (9)	−0.0082 (9)	0.0097 (8)
C37	0.0507 (9)	0.0572 (10)	0.0794 (12)	0.0122 (7)	−0.0023 (9)	0.0145 (9)
C38	0.0541 (9)	0.0588 (10)	0.0621 (10)	0.0131 (7)	0.0070 (8)	0.0168 (8)
O1	0.0676 (8)	0.0766 (8)	0.0653 (8)	−0.0072 (6)	0.0031 (6)	0.0079 (6)
O2	0.0733 (8)	0.0853 (9)	0.0667 (8)	−0.0125 (7)	−0.0006 (6)	0.0129 (6)

C1—C2	1.370 (2)	C20—C21	1.374 (2)
C1—C10	1.412 (2)	C20—C29	1.412 (2)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.417 (2)	C21—C22	1.419 (2)
C2—C11	1.493 (2)	C21—C30	1.490 (2)
C3—C4	1.360 (2)	C22—C23	1.358 (2)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.404 (2)	C23—C24	1.407 (2)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.415 (2)	C24—C25	1.415 (2)
C5—C10	1.420 (2)	C24—C29	1.424 (2)
C6—C7	1.356 (2)	C25—C26	1.356 (2)
C6—H6	0.9300	C25—H25	0.9300
C7—C8	1.397 (3)	C26—C27	1.400 (2)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.356 (2)	C27—C28	1.362 (2)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.414 (2)	C28—C29	1.415 (2)
C9—H9	0.9300	C28—H28	0.9300
C11—O1	1.2258 (18)	C30—O2	1.2184 (18)
C11—C12	1.471 (2)	C30—C31	1.485 (2)
C12—C13	1.325 (2)	C31—C32	1.324 (2)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.460 (2)	C32—C33	1.460 (2)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.391 (2)	C33—C34	1.392 (2)
C14—C19	1.397 (2)	C33—C38	1.399 (2)
C15—C16	1.383 (2)	C34—C35	1.374 (2)
C15—H15	0.9300	C34—H34	0.9300
C16—C17	1.375 (3)	C35—C36	1.375 (2)
C16—H16	0.9300	C35—H35	0.9300
C17—C18	1.376 (3)	C36—C37	1.374 (2)
C17—H17	0.9300	C36—H36	0.9300
C18—C19	1.377 (2)	C37—C38	1.371 (2)
C18—H18	0.9300	C37—H37	0.9300
C19—H19	0.9300	C38—H38	0.9300
C2—C1—C10	121.64 (14)	C21—C20—C29	121.38 (14)
C2—C1—H1	119.2	C21—C20—H20	119.3
C10—C1—H1	119.2	C29—C20—H20	119.3
C1—C2—C3	118.81 (14)	C20—C21—C22	119.00 (15)
C1—C2—C11	119.27 (14)	C20—C21—C30	119.14 (14)
C3—C2—C11	121.86 (14)	C22—C21—C30	121.86 (14)
C4—C3—C2	120.73 (15)	C23—C22—C21	120.81 (15)
C4—C3—H3	119.6	C23—C22—H22	119.6
C2—C3—H3	119.6	C21—C22—H22	119.6
C3—C4—C5	121.34 (15)	C22—C23—C24	121.21 (14)
C3—C4—H4	119.3	C22—C23—H23	119.4
C5—C4—H4	119.3	C24—C23—H23	119.4
C4—C5—C6	122.83 (15)	C23—C24—C25	122.72 (14)
C4—C5—C10	118.66 (14)	C23—C24—C29	118.78 (15)
C6—C5—C10	118.50 (15)	C25—C24—C29	118.49 (15)
C7—C6—C5	120.92 (16)	C26—C25—C24	121.06 (15)
C7—C6—H6	119.5	C26—C25—H25	119.5
C5—C6—H6	119.5	C24—C25—H25	119.5
C6—C7—C8	120.41 (17)	C25—C26—C27	120.53 (17)
C6—C7—H7	119.8	C25—C26—H26	119.7
C8—C7—H7	119.8	C27—C26—H26	119.7
C9—C8—C7	120.66 (17)	C28—C27—C26	120.38 (16)
C9—C8—H8	119.7	C28—C27—H27	119.8
C7—C8—H8	119.7	C26—C27—H27	119.8
C8—C9—C10	120.75 (16)	C27—C28—C29	120.85 (15)
C8—C9—H9	119.6	C27—C28—H28	119.6
C10—C9—H9	119.6	C29—C28—H28	119.6
C1—C10—C9	122.51 (14)	C20—C29—C28	122.54 (14)
C1—C10—C5	118.75 (14)	C20—C29—C24	118.78 (14)
C9—C10—C5	118.74 (15)	C28—C29—C24	118.68 (15)
O1—C11—C12	121.57 (15)	O2—C30—C31	121.21 (16)
O1—C11—C2	119.81 (15)	O2—C30—C21	120.69 (15)
C12—C11—C2	118.62 (13)	C31—C30—C21	118.09 (14)
C13—C12—C11	121.17 (15)	C32—C31—C30	121.54 (15)
C13—C12—H12	119.4	C32—C31—H31	119.2
C11—C12—H12	119.4	C30—C31—H31	119.2
C12—C13—C14	127.04 (15)	C31—C32—C33	127.23 (15)
C12—C13—H13	116.5	C31—C32—H32	116.4
C14—C13—H13	116.5	C33—C32—H32	116.4
C15—C14—C19	118.01 (16)	C34—C33—C38	118.17 (15)
C15—C14—C13	119.50 (14)	C34—C33—C32	119.13 (14)
C19—C14—C13	122.48 (15)	C38—C33—C32	122.70 (15)
C16—C15—C14	120.84 (16)	C35—C34—C33	120.51 (16)
C16—C15—H15	119.6	C35—C34—H34	119.7
C14—C15—H15	119.6	C33—C34—H34	119.7
C17—C16—C15	120.22 (17)	C34—C35—C36	120.51 (17)
C17—C16—H16	119.9	C34—C35—H35	119.7
C15—C16—H16	119.9	C36—C35—H35	119.7
C16—C17—C18	119.73 (18)	C37—C36—C35	119.78 (17)
C16—C17—H17	120.1	C37—C36—H36	120.1
C18—C17—H17	120.1	C35—C36—H36	120.1
C17—C18—C19	120.50 (16)	C38—C37—C36	120.42 (16)
C17—C18—H18	119.8	C38—C37—H37	119.8
C19—C18—H18	119.8	C36—C37—H37	119.8
C18—C19—C14	120.70 (16)	C37—C38—C33	120.61 (16)
C18—C19—H19	119.7	C37—C38—H38	119.7
C14—C19—H19	119.7	C33—C38—H38	119.7
C10—C1—C2—C3	−0.5 (2)	C29—C20—C21—C22	−0.4 (2)
C10—C1—C2—C11	−177.88 (13)	C29—C20—C21—C30	−179.62 (13)
C1—C2—C3—C4	−1.7 (2)	C20—C21—C22—C23	−1.7 (2)
C11—C2—C3—C4	175.60 (14)	C30—C21—C22—C23	177.56 (14)
C2—C3—C4—C5	2.1 (2)	C21—C22—C23—C24	2.1 (3)
C3—C4—C5—C6	179.33 (14)	C22—C23—C24—C25	178.04 (15)
C3—C4—C5—C10	−0.3 (2)	C22—C23—C24—C29	−0.5 (2)
C4—C5—C6—C7	−179.29 (15)	C23—C24—C25—C26	−177.69 (15)
C10—C5—C6—C7	0.3 (2)	C29—C24—C25—C26	0.9 (2)
C5—C6—C7—C8	0.4 (3)	C24—C25—C26—C27	−0.2 (3)
C6—C7—C8—C9	−0.3 (3)	C25—C26—C27—C28	−0.7 (3)
C7—C8—C9—C10	−0.6 (3)	C26—C27—C28—C29	0.9 (3)
C2—C1—C10—C9	−178.13 (14)	C21—C20—C29—C28	−177.50 (14)
C2—C1—C10—C5	2.3 (2)	C21—C20—C29—C24	1.9 (2)
C8—C9—C10—C1	−178.34 (15)	C27—C28—C29—C20	179.19 (14)
C8—C9—C10—C5	1.2 (2)	C27—C28—C29—C24	−0.2 (2)
C4—C5—C10—C1	−1.9 (2)	C23—C24—C29—C20	−1.5 (2)
C6—C5—C10—C1	178.51 (13)	C25—C24—C29—C20	179.91 (13)
C4—C5—C10—C9	178.52 (14)	C23—C24—C29—C28	177.96 (14)
C6—C5—C10—C9	−1.1 (2)	C25—C24—C29—C28	−0.7 (2)
C1—C2—C11—O1	26.3 (2)	C20—C21—C30—O2	27.6 (2)
C3—C2—C11—O1	−150.94 (16)	C22—C21—C30—O2	−151.59 (17)
C1—C2—C11—C12	−153.52 (15)	C20—C21—C30—C31	−152.83 (15)
C3—C2—C11—C12	29.2 (2)	C22—C21—C30—C31	27.9 (2)
O1—C11—C12—C13	14.7 (3)	O2—C30—C31—C32	12.3 (3)
C2—C11—C12—C13	−165.43 (15)	C21—C30—C31—C32	−167.26 (15)
C11—C12—C13—C14	−178.11 (14)	C30—C31—C32—C33	−177.63 (15)
C12—C13—C14—C15	−166.36 (16)	C31—C32—C33—C34	−168.95 (16)
C12—C13—C14—C19	12.8 (3)	C31—C32—C33—C38	11.4 (3)
C19—C14—C15—C16	−0.8 (2)	C38—C33—C34—C35	−0.7 (2)
C13—C14—C15—C16	178.42 (14)	C32—C33—C34—C35	179.67 (15)
C14—C15—C16—C17	0.7 (3)	C33—C34—C35—C36	0.2 (3)
C15—C16—C17—C18	−0.1 (3)	C34—C35—C36—C37	0.3 (3)
C16—C17—C18—C19	−0.4 (3)	C35—C36—C37—C38	−0.3 (3)
C17—C18—C19—C14	0.3 (3)	C36—C37—C38—C33	−0.2 (3)
C15—C14—C19—C18	0.3 (2)	C34—C33—C38—C37	0.7 (2)
C13—C14—C19—C18	−178.88 (14)	C32—C33—C38—C37	−179.68 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.49	2.814 (2)	101
C32—H32···O2	0.93	2.50	2.820 (2)	101
C18—H18···Cg1i	0.93	2.98	3.644	130
C15—H15···Cg2ii	0.93	2.94	3.642	134
C37—H37···Cg3iii	0.93	2.96	3.610	128
C1—H1···Cg5ii	0.93	2.97	3.611	127
C6—H6···Cg6iii	0.93	2.92	3.583	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1–C10, C5–C10, C14–C19, C20–C29 and C24–C29 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.49	2.814 (2)	101
C32—H32⋯O2	0.93	2.50	2.820 (2)	101
C18—H18⋯Cg1i	0.93	2.98	3.644	130
C15—H15⋯Cg2ii	0.93	2.94	3.642	134
C37—H37⋯Cg3iii	0.93	2.96	3.610	128
C1—H1⋯Cg5ii	0.93	2.97	3.611	127
C6—H6⋯Cg6iii	0.93	2.92	3.583	130

Symmetry codes: (i) ; (ii) ; (iii) .