(E)-3-(4-Chloro-phen-yl)-1-(5-hy-droxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(20)H(17)ClO(3), each having an E configuration about the -C=C- bond. The dihedral angles between the two benzene rings in the two mol-ecules are 7.17 (11) and 9.82 (11)°. In both mol-ecules, the hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond.

Related literature

For the biological activity of chalcones, see: Tran et al. (2009 ▶); Rao et al. (2004 ▶); Opletalova & Sedivy (1999 ▶); Dimmock et al. (1999 ▶). For related structures, see: Boeck et al. (2006 ▶); Jasinski et al. (2009 ▶); Wang & Yang (2011 ▶). For the synthesis of a related compound, see: Krohn et al. (2002 ▶).

Experimental

Crystal data

C20H17ClO3

M = 340.79

Monoclinic,

a = 11.0641 (7) Å

b = 9.8255 (5) Å

c = 30.7834 (14) Å

β = 91.177 (4)°

V = 3345.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.979, T max = 1.0

15168 measured reflections

6836 independent reflections

4040 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.145

S = 1.01

6836 reflections

439 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055255/lh5397sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055255/lh5397Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055255/lh5397Isup3.cml

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

C20H17ClO3	F(000) = 1424
Mr = 340.79	Dx = 1.353 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 3974 reflections
a = 11.0641 (7) Å	θ = 2.9–29.2°
b = 9.8255 (5) Å	µ = 0.24 mm−1
c = 30.7834 (14) Å	T = 293 K
β = 91.177 (4)°	Block, yellow
V = 3345.8 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur Eos diffractometer	6836 independent reflections
Radiation source: fine-focus sealed tube	4040 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −11→13
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2010)	k = −10→12
Tmin = 0.979, Tmax = 1.0	l = −38→38
15168 measured reflections

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) = 0.145	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.9761P] where P = (Fo2 + 2Fc2)/3
6836 reflections	(Δ/σ)max < 0.001
439 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.32 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
Cl1	0.17697 (7)	0.68585 (9)	0.12791 (2)	0.0832 (3)
Cl2	0.67696 (7)	0.18823 (9)	0.13224 (2)	0.0867 (3)
O1	0.43040 (13)	1.34774 (15)	−0.21832 (4)	0.0446 (4)
O2	0.55742 (17)	1.50025 (16)	−0.07889 (5)	0.0591 (5)
H2	0.5497	1.4826	−0.0531	0.089*
O3	0.49425 (19)	1.36093 (17)	−0.01377 (5)	0.0685 (6)
O4	0.92657 (15)	0.83125 (15)	−0.21812 (4)	0.0535 (4)
O5	1.05691 (17)	0.98927 (17)	−0.07956 (5)	0.0630 (5)
H5A	1.0497	0.9722	−0.0537	0.094*
O6	0.98945 (19)	0.85726 (18)	−0.01371 (5)	0.0702 (6)
C1	0.2403 (2)	0.8166 (3)	0.09786 (7)	0.0516 (6)
C2	0.3173 (2)	0.9068 (3)	0.11760 (7)	0.0601 (7)
H2A	0.3368	0.8980	0.1470	0.072*
C3	0.3659 (2)	1.0107 (3)	0.09376 (7)	0.0559 (7)
H3	0.4183	1.0722	0.1073	0.067*
C4	0.3383 (2)	1.0259 (2)	0.04984 (6)	0.0440 (5)
C5	0.2598 (2)	0.9333 (3)	0.03089 (7)	0.0603 (7)
H5	0.2401	0.9410	0.0015	0.072*
C6	0.2099 (2)	0.8296 (3)	0.05478 (7)	0.0645 (8)
H6	0.1561	0.7688	0.0417	0.077*
C7	0.3899 (2)	1.1385 (2)	0.02538 (7)	0.0484 (6)
H7	0.4321	1.2035	0.0416	0.058*
C8	0.3838 (2)	1.1588 (2)	−0.01696 (7)	0.0501 (6)
H8	0.3432	1.0958	−0.0345	0.060*
C9	0.4395 (2)	1.2785 (2)	−0.03733 (7)	0.0467 (6)
C10	0.4317 (2)	1.3002 (2)	−0.08425 (6)	0.0411 (5)
C11	0.4949 (2)	1.4095 (2)	−0.10305 (6)	0.0409 (5)
C12	0.4962 (2)	1.4278 (2)	−0.14818 (6)	0.0391 (5)
C13	0.43243 (19)	1.3360 (2)	−0.17420 (6)	0.0379 (5)
C14	0.3628 (2)	1.2328 (2)	−0.15658 (6)	0.0445 (6)
H14	0.3160	1.1766	−0.1745	0.053*
C15	0.3640 (2)	1.2151 (2)	−0.11228 (6)	0.0439 (5)
H15	0.3187	1.1449	−0.1005	0.053*
C16	0.5543 (2)	1.5420 (2)	−0.16934 (7)	0.0481 (6)
H16	0.5829	1.6151	−0.1529	0.058*
C17	0.5664 (2)	1.5415 (2)	−0.21202 (7)	0.0469 (6)
H17	0.5973	1.6179	−0.2257	0.056*
C18	0.5310 (2)	1.4197 (2)	−0.23871 (6)	0.0409 (5)
C19	0.6367 (2)	1.3223 (2)	−0.24194 (7)	0.0521 (6)
H19A	0.6611	1.2928	−0.2133	0.078*
H19C	0.7030	1.3675	−0.2554	0.078*
H19B	0.6128	1.2448	−0.2591	0.078*
C20	0.4809 (2)	1.4566 (2)	−0.28360 (7)	0.0533 (6)
H20A	0.4528	1.3756	−0.2981	0.080*
H20C	0.5433	1.4981	−0.3003	0.080*
H20B	0.4149	1.5191	−0.2808	0.080*
C21	0.7398 (2)	0.3173 (3)	0.10131 (7)	0.0540 (6)
C22	0.8127 (2)	0.4117 (3)	0.12071 (7)	0.0647 (7)
H22	0.8297	0.4070	0.1504	0.078*
C23	0.8612 (2)	0.5144 (3)	0.09617 (7)	0.0601 (7)
H23	0.9112	0.5787	0.1095	0.072*
C24	0.8371 (2)	0.5239 (2)	0.05185 (7)	0.0467 (6)
C25	0.7623 (3)	0.4268 (3)	0.03335 (7)	0.0627 (7)
H25	0.7445	0.4308	0.0037	0.075*
C26	0.7131 (3)	0.3235 (3)	0.05785 (8)	0.0672 (8)
H26	0.6625	0.2591	0.0449	0.081*
C27	0.8875 (2)	0.6353 (2)	0.02659 (7)	0.0498 (6)
H27	0.9296	0.7014	0.0423	0.060*
C28	0.8806 (2)	0.6535 (2)	−0.01581 (7)	0.0514 (6)
H28	0.8402	0.5894	−0.0329	0.062*
C29	0.9352 (2)	0.7731 (2)	−0.03680 (7)	0.0478 (6)
C30	0.9275 (2)	0.7921 (2)	−0.08387 (6)	0.0423 (5)
C31	0.9920 (2)	0.8995 (2)	−0.10336 (7)	0.0440 (5)
C32	0.9926 (2)	0.9147 (2)	−0.14846 (7)	0.0428 (5)
C33	0.9251 (2)	0.8254 (2)	−0.17399 (6)	0.0423 (5)
C34	0.8573 (2)	0.7219 (2)	−0.15562 (7)	0.0482 (6)
H34	0.8108	0.6644	−0.1732	0.058*
C35	0.8599 (2)	0.7056 (2)	−0.11134 (7)	0.0468 (6)
H35	0.8156	0.6353	−0.0992	0.056*
C36	1.0660 (2)	1.0162 (2)	−0.17048 (8)	0.0536 (6)
H36	1.1210	1.0689	−0.1546	0.064*
C37	1.0540 (2)	1.0329 (2)	−0.21284 (7)	0.0516 (6)
H37	1.1061	1.0921	−0.2268	0.062*
C38	0.9593 (2)	0.9595 (2)	−0.23919 (7)	0.0463 (6)
C39	0.8463 (2)	1.0461 (3)	−0.24342 (8)	0.0666 (7)
H39B	0.7852	0.9969	−0.2595	0.100*
H39C	0.8648	1.1289	−0.2584	0.100*
H39A	0.8173	1.0671	−0.2150	0.100*
C40	1.0025 (3)	0.9172 (3)	−0.28349 (7)	0.0618 (7)
H40B	1.0746	0.8635	−0.2802	0.093*
H40C	1.0195	0.9968	−0.3004	0.093*
H40A	0.9408	0.8644	−0.2980	0.093*

	U11	U22	U33	U12	U13	U23
Cl1	0.0787 (6)	0.1037 (6)	0.0670 (4)	−0.0313 (5)	0.0003 (4)	0.0278 (4)
Cl2	0.0782 (6)	0.1026 (6)	0.0797 (5)	−0.0145 (5)	0.0132 (4)	0.0333 (4)
O1	0.0441 (9)	0.0561 (10)	0.0337 (8)	−0.0075 (8)	0.0009 (6)	−0.0009 (7)
O2	0.0831 (14)	0.0533 (10)	0.0405 (8)	−0.0213 (9)	−0.0060 (9)	−0.0060 (8)
O3	0.1044 (16)	0.0582 (11)	0.0422 (9)	−0.0197 (11)	−0.0150 (9)	0.0015 (8)
O4	0.0721 (12)	0.0492 (10)	0.0393 (8)	−0.0154 (9)	0.0071 (8)	−0.0031 (7)
O5	0.0772 (14)	0.0610 (11)	0.0502 (9)	−0.0267 (10)	−0.0132 (9)	−0.0005 (8)
O6	0.0999 (16)	0.0619 (11)	0.0480 (10)	−0.0190 (11)	−0.0197 (10)	0.0024 (8)
C1	0.0450 (15)	0.0673 (16)	0.0428 (13)	−0.0030 (13)	0.0042 (10)	0.0080 (11)
C2	0.0624 (18)	0.0832 (19)	0.0345 (12)	−0.0096 (15)	−0.0052 (11)	0.0073 (12)
C3	0.0566 (17)	0.0716 (17)	0.0391 (13)	−0.0122 (14)	−0.0081 (11)	0.0006 (11)
C4	0.0433 (14)	0.0540 (14)	0.0349 (11)	0.0028 (12)	0.0027 (10)	−0.0011 (10)
C5	0.0686 (19)	0.0784 (19)	0.0335 (12)	−0.0145 (15)	−0.0063 (11)	0.0046 (12)
C6	0.0683 (19)	0.0797 (19)	0.0452 (14)	−0.0226 (16)	−0.0072 (12)	0.0014 (13)
C7	0.0508 (15)	0.0553 (15)	0.0392 (12)	0.0003 (12)	0.0000 (10)	−0.0002 (10)
C8	0.0603 (17)	0.0491 (14)	0.0408 (13)	0.0001 (13)	0.0013 (11)	−0.0001 (10)
C9	0.0553 (16)	0.0445 (13)	0.0402 (12)	0.0027 (12)	−0.0015 (11)	−0.0032 (10)
C10	0.0477 (14)	0.0390 (12)	0.0366 (11)	0.0005 (11)	0.0021 (10)	−0.0033 (9)
C11	0.0452 (14)	0.0377 (12)	0.0395 (12)	−0.0006 (11)	−0.0041 (10)	−0.0063 (9)
C12	0.0411 (13)	0.0376 (12)	0.0386 (11)	0.0015 (10)	−0.0007 (9)	−0.0018 (9)
C13	0.0343 (12)	0.0441 (13)	0.0355 (11)	0.0030 (10)	0.0022 (9)	−0.0034 (9)
C14	0.0432 (14)	0.0500 (14)	0.0404 (12)	−0.0108 (11)	0.0026 (10)	−0.0076 (10)
C15	0.0476 (15)	0.0432 (13)	0.0411 (12)	−0.0072 (11)	0.0073 (10)	−0.0018 (10)
C16	0.0571 (16)	0.0360 (12)	0.0510 (14)	−0.0045 (12)	−0.0049 (11)	−0.0018 (10)
C17	0.0550 (16)	0.0368 (13)	0.0490 (13)	−0.0016 (11)	0.0012 (11)	0.0077 (10)
C18	0.0443 (14)	0.0405 (12)	0.0382 (11)	−0.0007 (11)	0.0049 (9)	0.0050 (9)
C19	0.0473 (15)	0.0524 (15)	0.0568 (14)	0.0042 (12)	0.0057 (11)	0.0022 (11)
C20	0.0617 (17)	0.0558 (15)	0.0424 (13)	0.0031 (13)	0.0019 (11)	0.0068 (11)
C21	0.0438 (15)	0.0686 (17)	0.0499 (14)	0.0008 (13)	0.0075 (11)	0.0114 (12)
C22	0.0641 (19)	0.092 (2)	0.0375 (13)	−0.0050 (17)	−0.0026 (12)	0.0111 (13)
C23	0.0592 (18)	0.0791 (19)	0.0416 (13)	−0.0120 (15)	−0.0078 (11)	0.0018 (12)
C24	0.0404 (14)	0.0597 (15)	0.0401 (12)	0.0030 (12)	0.0029 (10)	−0.0010 (11)
C25	0.0721 (19)	0.0786 (19)	0.0371 (13)	−0.0127 (16)	−0.0021 (12)	0.0018 (12)
C26	0.072 (2)	0.0755 (19)	0.0543 (16)	−0.0215 (16)	0.0037 (13)	−0.0004 (13)
C27	0.0474 (15)	0.0563 (15)	0.0458 (13)	−0.0008 (12)	−0.0012 (11)	−0.0012 (11)
C28	0.0606 (17)	0.0499 (14)	0.0437 (13)	−0.0044 (13)	0.0015 (11)	−0.0003 (10)
C29	0.0530 (16)	0.0455 (14)	0.0445 (13)	0.0019 (12)	−0.0050 (11)	−0.0018 (10)
C30	0.0445 (14)	0.0411 (13)	0.0413 (12)	0.0000 (11)	0.0000 (10)	−0.0025 (10)
C31	0.0420 (14)	0.0421 (13)	0.0477 (13)	−0.0043 (11)	−0.0040 (10)	−0.0030 (10)
C32	0.0413 (14)	0.0412 (13)	0.0459 (12)	−0.0028 (11)	0.0018 (10)	−0.0004 (10)
C33	0.0456 (14)	0.0446 (13)	0.0369 (12)	−0.0017 (11)	0.0044 (10)	−0.0045 (10)
C34	0.0539 (16)	0.0458 (14)	0.0449 (13)	−0.0144 (12)	0.0037 (11)	−0.0081 (10)
C35	0.0520 (15)	0.0451 (13)	0.0437 (13)	−0.0082 (12)	0.0063 (10)	−0.0002 (10)
C36	0.0506 (16)	0.0522 (15)	0.0577 (15)	−0.0150 (13)	−0.0043 (11)	0.0048 (12)
C37	0.0469 (15)	0.0505 (14)	0.0576 (15)	−0.0085 (12)	0.0052 (11)	0.0104 (11)
C38	0.0502 (15)	0.0448 (13)	0.0441 (12)	−0.0023 (12)	0.0058 (10)	0.0018 (10)
C39	0.0501 (17)	0.0729 (19)	0.0768 (18)	0.0113 (15)	−0.0021 (13)	−0.0082 (14)
C40	0.077 (2)	0.0615 (17)	0.0480 (14)	0.0043 (15)	0.0155 (13)	0.0049 (12)

Cl1—C1	1.739 (2)	C19—H19A	0.9600
Cl2—C21	1.739 (2)	C19—H19C	0.9600
O1—C13	1.363 (2)	C19—H19B	0.9600
O1—C18	1.471 (2)	C20—H20A	0.9600
O2—H2	0.8200	C20—H20C	0.9600
O2—C11	1.343 (2)	C20—H20B	0.9600
O3—C9	1.237 (3)	C21—C22	1.360 (3)
O4—C33	1.360 (2)	C21—C26	1.365 (3)
O4—C38	1.466 (3)	C22—H22	0.9300
O5—H5A	0.8200	C22—C23	1.376 (3)
O5—C31	1.345 (2)	C23—H23	0.9300
O6—C29	1.237 (3)	C23—C24	1.388 (3)
C1—C2	1.363 (3)	C24—C25	1.379 (3)
C1—C6	1.367 (3)	C24—C27	1.460 (3)
C2—H2A	0.9300	C25—H25	0.9300
C2—C3	1.374 (3)	C25—C26	1.382 (3)
C3—H3	0.9300	C26—H26	0.9300
C3—C4	1.388 (3)	C27—H27	0.9300
C4—C5	1.379 (3)	C27—C28	1.318 (3)
C4—C7	1.461 (3)	C28—H28	0.9300
C5—H5	0.9300	C28—C29	1.477 (3)
C5—C6	1.379 (3)	C29—C30	1.462 (3)
C6—H6	0.9300	C30—C31	1.415 (3)
C7—H7	0.9300	C30—C35	1.404 (3)
C7—C8	1.319 (3)	C31—C32	1.397 (3)
C8—H8	0.9300	C32—C33	1.386 (3)
C8—C9	1.474 (3)	C32—C36	1.461 (3)
C9—C10	1.461 (3)	C33—C34	1.390 (3)
C10—C11	1.412 (3)	C34—H34	0.9300
C10—C15	1.407 (3)	C34—C35	1.372 (3)
C11—C12	1.401 (3)	C35—H35	0.9300
C12—C13	1.389 (3)	C36—H36	0.9300
C12—C16	1.454 (3)	C36—C37	1.318 (3)
C13—C14	1.390 (3)	C37—H37	0.9300
C14—H14	0.9300	C37—C38	1.497 (3)
C14—C15	1.375 (3)	C38—C39	1.515 (3)
C15—H15	0.9300	C38—C40	1.513 (3)
C16—H16	0.9300	C39—H39B	0.9600
C16—C17	1.323 (3)	C39—H39C	0.9600
C17—H17	0.9300	C39—H39A	0.9600
C17—C18	1.498 (3)	C40—H40B	0.9600
C18—C19	1.516 (3)	C40—H40C	0.9600
C18—C20	1.522 (3)	C40—H40A	0.9600
O1—C13—C12	121.14 (19)	C18—C20—H20C	109.5
O1—C13—C14	116.92 (18)	C18—C20—H20B	109.5
O1—C18—C17	109.95 (17)	C19—C18—C20	110.97 (18)
O1—C18—C19	108.40 (17)	H19A—C19—H19C	109.5
O1—C18—C20	103.70 (17)	H19A—C19—H19B	109.5
O2—C11—C10	122.11 (18)	H19C—C19—H19B	109.5
O2—C11—C12	116.62 (19)	H20A—C20—H20C	109.5
O3—C9—C8	118.49 (19)	H20A—C20—H20B	109.5
O3—C9—C10	120.2 (2)	H20C—C20—H20B	109.5
O4—C33—C32	121.5 (2)	C21—C22—H22	120.2
O4—C33—C34	117.05 (19)	C21—C22—C23	119.6 (2)
O4—C38—C37	110.53 (18)	C21—C26—C25	119.2 (2)
O4—C38—C39	108.0 (2)	C21—C26—H26	120.4
O4—C38—C40	104.35 (18)	C22—C21—Cl2	119.83 (19)
O5—C31—C30	121.79 (19)	C22—C21—C26	120.9 (2)
O5—C31—C32	117.2 (2)	C22—C23—H23	119.3
O6—C29—C28	118.6 (2)	C22—C23—C24	121.3 (2)
O6—C29—C30	120.2 (2)	C23—C22—H22	120.2
C1—C2—H2A	120.2	C23—C24—C27	120.4 (2)
C1—C2—C3	119.5 (2)	C24—C23—H23	119.3
C1—C6—C5	119.5 (2)	C24—C25—H25	119.3
C1—C6—H6	120.2	C24—C25—C26	121.5 (2)
C2—C1—Cl1	119.86 (18)	C24—C27—H27	116.1
C2—C1—C6	120.7 (2)	C25—C24—C23	117.5 (2)
C2—C3—H3	119.4	C25—C24—C27	122.1 (2)
C2—C3—C4	121.3 (2)	C25—C26—H26	120.4
C3—C2—H2A	120.2	C26—C21—Cl2	119.2 (2)
C3—C4—C7	120.2 (2)	C26—C25—H25	119.3
C4—C3—H3	119.4	C27—C28—H28	119.2
C4—C5—H5	119.4	C27—C28—C29	121.7 (2)
C4—C7—H7	116.2	C28—C27—C24	127.9 (2)
C5—C4—C3	117.7 (2)	C28—C27—H27	116.1
C5—C4—C7	122.10 (19)	C29—C28—H28	119.2
C5—C6—H6	120.2	C30—C29—C28	121.3 (2)
C6—C1—Cl1	119.4 (2)	C30—C35—H35	119.1
C6—C5—C4	121.2 (2)	C31—O5—H5A	109.5
C6—C5—H5	119.4	C31—C30—C29	119.70 (19)
C7—C8—H8	119.1	C31—C32—C36	123.3 (2)
C7—C8—C9	121.9 (2)	C32—C31—C30	120.97 (19)
C8—C7—C4	127.7 (2)	C32—C33—C34	121.43 (19)
C8—C7—H7	116.2	C32—C36—H36	120.0
C9—C8—H8	119.1	C33—O4—C38	119.11 (16)
C10—C9—C8	121.3 (2)	C33—C32—C31	118.8 (2)
C10—C15—H15	119.1	C33—C32—C36	117.84 (19)
C11—O2—H2	109.5	C33—C34—H34	120.4
C11—C10—C9	119.75 (19)	C34—C35—C30	121.8 (2)
C11—C12—C16	123.84 (19)	C34—C35—H35	119.1
C12—C11—C10	121.26 (18)	C35—C30—C29	122.7 (2)
C12—C13—C14	121.85 (18)	C35—C30—C31	117.61 (19)
C12—C16—H16	120.1	C35—C34—C33	119.3 (2)
C13—O1—C18	117.98 (15)	C35—C34—H34	120.4
C13—C12—C11	118.22 (19)	C36—C37—H37	119.0
C13—C12—C16	117.84 (18)	C36—C37—C38	122.0 (2)
C13—C14—H14	120.5	C37—C36—C32	119.9 (2)
C14—C15—C10	121.9 (2)	C37—C36—H36	120.0
C14—C15—H15	119.1	C37—C38—C39	110.1 (2)
C15—C10—C9	122.7 (2)	C37—C38—C40	113.0 (2)
C15—C10—C11	117.56 (18)	C38—C37—H37	119.0
C15—C14—C13	119.01 (19)	C38—C39—H39B	109.5
C15—C14—H14	120.5	C38—C39—H39C	109.5
C16—C17—H17	119.4	C38—C39—H39A	109.5
C16—C17—C18	121.1 (2)	C38—C40—H40B	109.5
C17—C16—C12	119.8 (2)	C38—C40—H40C	109.5
C17—C16—H16	120.1	C38—C40—H40A	109.5
C17—C18—C19	110.31 (19)	H39B—C39—H39C	109.5
C17—C18—C20	113.22 (18)	H39B—C39—H39A	109.5
C18—C17—H17	119.4	H39C—C39—H39A	109.5
C18—C19—H19A	109.5	C40—C38—C39	110.63 (19)
C18—C19—H19C	109.5	H40B—C40—H40C	109.5
C18—C19—H19B	109.5	H40B—C40—H40A	109.5
C18—C20—H20A	109.5	H40C—C40—H40A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.82	2.537 (2)	146.
O5—H5A···O6	0.82	1.81	2.532 (2)	147.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.82	2.537 (2)	146
O5—H5A⋯O6	0.82	1.81	2.532 (2)	147