2-Benzyl­idene-2,3-dihydro-1H-benzo[f]chromen-1-one

The dihedral angles between the phenyl ring and the naphthalene part of the chromanone unit in the two independent mol­ecules of the title compound, C₂₀H₁₄O₂, are 56.17 (4) and 55.62 (7)°. The mol­ecular structure is stabilized by weak intra­molecular C—H...O inter­actions and the crystal packing is stabilized by weak C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.061
• Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.24

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2881
           Count of symmetry unique reflns         2881
           Completeness (_total/calc)            100.00%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The chromanone moiety present in the title compound consisting of the pyrone and benzene rings, which plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001). The naturally occurring classes of compounds to which they belong, the benzylidene chroman-4-ones, have identified as a potential source of new anti-fungal agents (Kang et al., 2004).

The geometric parameters in the title compound agree with the reported values of similar structure (Puviarasan et al., 1998; Wu et al., 2005a,b; Schollmeyer et al., 2005; Nissa et al., 2001). The dihedral angles between the phenyl ring and the benzene ring of chromanone unit in the two crystallographically independent molecules are 56.17 (4) and 55.62 (7)°.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak C—H···π interactions.

Related literature

For related literature see: Puviarasan et al. (1998); Tillekeratne et al. (2001); Nissa et al. (2001); Kang et al. (2004); Wu et al. (2005a,b); Schollmeyer et al. (2005). Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings,

respectively.

S2. Experimental

Bromomethyl-3-phenyl-propenoate (10 mmol) was treated with beta-napthanol (10 mmol) in the presence of potassium carbonate in acetone at reflux temperature for 3 h. The napthoxy ester of methyl- 3-phenyl-2-(2-methoxy-4-prop-2-enyl) phenoxy methyl-prop-2-enoate was obtained after silica gel column chromatography (3% EtOAc-hexane). Hydrolysis of this ester was carried out with KOH in aqueous 1,4-dioxane at room temperature. The reaction mixture was acidified and the precipitated acid was purified by recrystalization. Finally the acid was treated with TFAA and the reaction mixture refluxed in dichloromethane for 1 h. It was further purified by column chromatography (silica gel - 3% EtOAc-hexane).

S3. Refinement

H atoms were positioned geometrically (C—H = 0.95 or 0.99 Å) and refined using riding model, with U_iso(H) = 1.2U_eq(C). In the absence of significant anomalous scattering effects, Friedel pairs have been merged.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The asymmetric unit of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

2-Benzylidene-2,3-dihydro-1H-benzo[f]chromen-1-one

Crystal data

C20H14O2	F(000) = 1200
Mr = 286.31	Dx = 1.338 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 30955 reflections
a = 12.3567 (6) Å	θ = 1.7–27.2°
b = 11.2675 (5) Å	µ = 0.09 mm^−1
c = 20.4103 (12) Å	T = 150 K
V = 2841.7 (3) Å^3	Prism, yellow
Z = 8	0.32 × 0.23 × 0.18 mm

Data collection

Stoe IPDS2 diffractometer	2881 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.105
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
rotation method scans	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.973, Tmax = 0.985	l = −25→25
33648 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0267P)^2] where P = (Fo^2 + 2Fc^2)/3
2881 reflections	(Δ/σ)max = 0.001
398 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1622 (2)	−0.0440 (3)	0.23909 (15)	0.0308 (6)
C2	0.1523 (2)	−0.1118 (3)	0.29624 (14)	0.0377 (7)
H2	0.2018	−0.1746	0.3042	0.045*
C3	0.0716 (2)	−0.0885 (3)	0.34113 (16)	0.0444 (8)
H3	0.0661	−0.1352	0.3797	0.053*
C4	−0.0014 (3)	0.0026 (2)	0.3303 (2)	0.0384 (10)
H4	−0.0560	0.0195	0.3617	0.046*
C5	0.0056 (2)	0.0686 (3)	0.27360 (17)	0.0380 (7)
H5	−0.0453	0.1301	0.2657	0.046*
C6	0.0866 (2)	0.0461 (3)	0.22768 (16)	0.0334 (7)
H6	0.0905	0.0919	0.1887	0.040*
C7	0.2507 (2)	−0.0713 (2)	0.19390 (15)	0.0322 (6)
H7	0.2714	−0.1524	0.1925	0.039*
C8	0.3068 (3)	0.0006 (2)	0.1543 (2)	0.0292 (9)
C9	0.3951 (2)	−0.0516 (2)	0.11341 (15)	0.0317 (7)
C10	0.4700 (2)	0.0332 (3)	0.08277 (15)	0.0307 (7)
C11	0.5574 (3)	−0.0012 (2)	0.0393 (2)	0.0283 (9)
C12	0.5704 (2)	−0.1172 (3)	0.01372 (14)	0.0341 (7)
H12	0.5198	−0.1770	0.0255	0.041*
C13	0.6539 (2)	−0.1451 (3)	−0.02748 (15)	0.0384 (7)
H13	0.6595	−0.2233	−0.0446	0.046*
C14	0.7310 (3)	−0.0600 (3)	−0.04466 (16)	0.0406 (8)
H14	0.7897	−0.0804	−0.0726	0.049*
C15	0.7213 (3)	0.0530 (3)	−0.02093 (17)	0.0395 (9)
H15	0.7739	0.1107	−0.0326	0.047*
C16	0.6352 (2)	0.0857 (2)	0.02037 (14)	0.0325 (7)
C17	0.6268 (2)	0.2029 (3)	0.04455 (14)	0.0372 (7)
H17	0.6802	0.2598	0.0330	0.045*
C18	0.5439 (2)	0.2354 (2)	0.08387 (15)	0.0362 (7)
H18	0.5388	0.3149	0.0991	0.043*
C19	0.4647 (2)	0.1511 (3)	0.10228 (15)	0.0319 (7)
C20	0.2890 (2)	0.1306 (2)	0.14782 (16)	0.0354 (7)
H20A	0.2442	0.1460	0.1085	0.043*
H20B	0.2484	0.1593	0.1865	0.043*
C21	0.5995 (2)	0.5378 (3)	0.18920 (15)	0.0312 (7)
C22	0.6709 (2)	0.4432 (3)	0.19898 (16)	0.0357 (7)
H22	0.6618	0.3924	0.2357	0.043*
C23	0.7547 (2)	0.4230 (3)	0.15543 (17)	0.0390 (7)
H23	0.8018	0.3574	0.1619	0.047*
C24	0.7703 (3)	0.4972 (2)	0.1031 (2)	0.0413 (10)
H24	0.8287	0.4834	0.0738	0.050*
C25	0.7012 (2)	0.5924 (3)	0.09264 (16)	0.0408 (7)
H25	0.7112	0.6430	0.0559	0.049*
C26	0.6172 (2)	0.6127 (2)	0.13634 (14)	0.0358 (7)
H26	0.5710	0.6792	0.1300	0.043*
C27	0.5093 (2)	0.5654 (3)	0.23332 (14)	0.0323 (7)
H27	0.4904	0.6470	0.2354	0.039*
C28	0.4494 (3)	0.4940 (2)	0.2711 (2)	0.0311 (10)
C29	0.3629 (2)	0.5486 (3)	0.31194 (14)	0.0310 (7)
C30	0.2851 (2)	0.4663 (3)	0.34178 (15)	0.0290 (6)
C31	0.2010 (3)	0.5032 (2)	0.3862 (2)	0.0285 (9)
C32	0.1977 (2)	0.6160 (3)	0.41633 (14)	0.0335 (7)
H32	0.2536	0.6717	0.4076	0.040*
C33	0.1151 (2)	0.6464 (3)	0.45793 (14)	0.0378 (7)
H33	0.1158	0.7222	0.4783	0.045*
C34	0.0293 (3)	0.5679 (3)	0.47106 (17)	0.0391 (8)
H34	−0.0288	0.5914	0.4986	0.047*
C35	0.0308 (3)	0.4586 (3)	0.44398 (16)	0.0363 (8)
H35	−0.0261	0.4046	0.4535	0.044*
C36	0.1155 (2)	0.4227 (3)	0.40164 (14)	0.0326 (7)
C37	0.1164 (2)	0.3071 (2)	0.37394 (14)	0.0354 (7)
H37	0.0585	0.2542	0.3833	0.042*
C38	0.1981 (2)	0.2705 (3)	0.33438 (14)	0.0353 (7)
H38	0.1981	0.1923	0.3170	0.042*
C39	0.2830 (2)	0.3498 (3)	0.31937 (15)	0.0310 (7)
C40	0.4609 (2)	0.3623 (2)	0.27652 (16)	0.0354 (7)
H40A	0.5029	0.3326	0.2386	0.042*
H40B	0.5020	0.3431	0.3168	0.042*
O1	0.40678 (16)	−0.16006 (19)	0.10971 (12)	0.0423 (6)
O2	0.38869 (16)	0.19617 (18)	0.14242 (10)	0.0380 (5)
O3	0.35498 (16)	0.65771 (18)	0.31632 (12)	0.0381 (5)
O4	0.35807 (14)	0.30302 (19)	0.27852 (10)	0.0381 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0286 (15)	0.0270 (16)	0.0369 (18)	−0.0049 (13)	−0.0027 (14)	−0.0051 (15)
C2	0.0379 (17)	0.0339 (16)	0.0413 (18)	0.0000 (13)	−0.0016 (14)	0.0032 (14)
C3	0.0447 (18)	0.046 (2)	0.0428 (19)	−0.0055 (15)	0.0031 (15)	0.0042 (16)
C4	0.0350 (18)	0.039 (2)	0.041 (2)	−0.0061 (13)	0.0028 (17)	−0.0058 (13)
C5	0.0272 (15)	0.0331 (16)	0.054 (2)	−0.0025 (12)	−0.0041 (15)	−0.0053 (15)
C6	0.0317 (16)	0.0319 (18)	0.0367 (18)	−0.0046 (13)	−0.0026 (14)	0.0014 (14)
C7	0.0293 (14)	0.0276 (14)	0.0398 (17)	−0.0014 (12)	−0.0023 (13)	−0.0023 (13)
C8	0.0285 (18)	0.026 (2)	0.033 (2)	0.0008 (11)	−0.0053 (16)	−0.0023 (11)
C9	0.0310 (16)	0.0253 (19)	0.0390 (18)	−0.0029 (12)	−0.0047 (13)	−0.0002 (14)
C10	0.0331 (17)	0.0302 (15)	0.0289 (17)	−0.0031 (14)	−0.0063 (14)	−0.0002 (15)
C11	0.0317 (19)	0.024 (2)	0.029 (2)	−0.0013 (11)	−0.0034 (15)	0.0002 (11)
C12	0.0392 (17)	0.0302 (17)	0.0329 (17)	−0.0038 (13)	−0.0001 (13)	−0.0030 (13)
C13	0.0442 (17)	0.0337 (17)	0.0372 (17)	−0.0009 (14)	−0.0015 (15)	−0.0044 (14)
C14	0.0405 (18)	0.0408 (19)	0.040 (2)	−0.0040 (15)	0.0070 (15)	−0.0032 (16)
C15	0.0437 (19)	0.034 (2)	0.041 (2)	−0.0082 (15)	0.0055 (16)	−0.0024 (16)
C16	0.0343 (16)	0.0326 (17)	0.0305 (16)	−0.0068 (13)	−0.0044 (13)	−0.0010 (12)
C17	0.0395 (17)	0.0301 (16)	0.0419 (17)	−0.0087 (13)	0.0006 (14)	−0.0025 (13)
C18	0.0447 (17)	0.0230 (15)	0.0409 (17)	−0.0063 (13)	0.0019 (15)	−0.0041 (13)
C19	0.0340 (15)	0.0295 (15)	0.0323 (17)	0.0000 (13)	−0.0036 (14)	−0.0015 (13)
C20	0.0322 (16)	0.0315 (17)	0.0426 (18)	−0.0022 (12)	−0.0007 (14)	0.0005 (13)
C21	0.0322 (17)	0.0298 (16)	0.0315 (17)	−0.0020 (14)	−0.0035 (14)	−0.0061 (15)
C22	0.0303 (16)	0.0330 (18)	0.0439 (19)	−0.0034 (13)	−0.0071 (14)	−0.0030 (14)
C23	0.0307 (15)	0.0337 (16)	0.053 (2)	0.0004 (13)	−0.0015 (15)	−0.0083 (15)
C24	0.0343 (18)	0.045 (2)	0.045 (2)	−0.0030 (13)	0.0066 (17)	−0.0139 (15)
C25	0.0446 (17)	0.0393 (18)	0.0384 (18)	−0.0059 (15)	0.0011 (15)	−0.0025 (14)
C26	0.0333 (15)	0.0339 (15)	0.0401 (16)	0.0003 (13)	−0.0018 (14)	−0.0004 (14)
C27	0.0335 (16)	0.0285 (15)	0.0349 (17)	0.0014 (12)	−0.0082 (14)	−0.0036 (13)
C28	0.0295 (18)	0.030 (2)	0.033 (2)	0.0011 (12)	−0.0031 (16)	−0.0040 (12)
C29	0.0320 (17)	0.0292 (19)	0.0317 (16)	0.0006 (12)	−0.0043 (13)	−0.0036 (14)
C30	0.0288 (16)	0.0269 (15)	0.0311 (17)	0.0020 (13)	−0.0020 (13)	−0.0004 (15)
C31	0.0304 (19)	0.031 (2)	0.024 (2)	0.0022 (11)	−0.0061 (15)	0.0011 (11)
C32	0.0327 (16)	0.0326 (16)	0.0353 (17)	0.0001 (12)	−0.0014 (13)	−0.0003 (14)
C33	0.0413 (16)	0.0329 (16)	0.0392 (17)	0.0021 (13)	0.0041 (14)	−0.0030 (13)
C34	0.0342 (16)	0.046 (2)	0.037 (2)	0.0023 (15)	0.0035 (14)	0.0011 (16)
C35	0.0310 (16)	0.043 (2)	0.035 (2)	−0.0028 (15)	0.0002 (14)	0.0057 (16)
C36	0.0360 (16)	0.0308 (16)	0.0312 (16)	−0.0001 (14)	−0.0057 (14)	0.0029 (13)
C37	0.0376 (16)	0.0309 (16)	0.0377 (16)	−0.0068 (13)	−0.0062 (14)	0.0053 (13)
C38	0.0378 (17)	0.0299 (16)	0.0382 (17)	−0.0036 (13)	−0.0030 (14)	0.0015 (13)
C39	0.0357 (17)	0.0293 (15)	0.0278 (16)	0.0021 (13)	−0.0011 (14)	−0.0025 (13)
C40	0.0335 (15)	0.0323 (16)	0.0403 (17)	−0.0003 (12)	0.0010 (14)	−0.0028 (14)
O1	0.0428 (13)	0.0256 (13)	0.0584 (15)	−0.0023 (10)	0.0090 (12)	−0.0049 (11)
O2	0.0378 (11)	0.0292 (12)	0.0469 (14)	−0.0042 (9)	0.0059 (10)	−0.0066 (11)
O3	0.0386 (12)	0.0240 (13)	0.0519 (15)	0.0005 (9)	0.0078 (11)	−0.0032 (10)
O4	0.0379 (12)	0.0319 (12)	0.0446 (14)	−0.0030 (9)	0.0061 (10)	−0.0061 (10)

Geometric parameters (Å, º)

C1—C6	1.398 (5)	C21—C26	1.387 (4)
C1—C2	1.400 (4)	C21—C22	1.398 (4)
C1—C7	1.463 (4)	C21—C27	1.466 (4)
C2—C3	1.380 (4)	C22—C23	1.383 (4)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.383 (4)	C23—C24	1.370 (5)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.378 (5)	C24—C25	1.387 (4)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.394 (4)	C25—C26	1.387 (4)
C5—H5	0.9500	C25—H25	0.9500
C6—H6	0.9500	C26—H26	0.9500
C7—C8	1.338 (4)	C27—C28	1.338 (4)
C7—H7	0.9500	C27—H27	0.9500
C8—C20	1.487 (3)	C28—C29	1.488 (5)
C8—C9	1.493 (5)	C28—C40	1.494 (4)
C9—O1	1.233 (3)	C29—O3	1.237 (3)
C9—C10	1.470 (4)	C29—C30	1.467 (4)
C10—C19	1.388 (4)	C30—C39	1.391 (4)
C10—C11	1.451 (5)	C30—C31	1.440 (5)
C11—C12	1.416 (4)	C31—C32	1.412 (4)
C11—C16	1.426 (4)	C31—C36	1.429 (5)
C12—C13	1.368 (4)	C32—C33	1.372 (4)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.396 (4)	C33—C34	1.406 (4)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.368 (5)	C34—C35	1.350 (5)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.407 (4)	C35—C36	1.416 (4)
C15—H15	0.9500	C35—H35	0.9500
C16—C17	1.413 (4)	C36—C37	1.420 (4)
C17—C18	1.352 (4)	C37—C38	1.357 (4)
C17—H17	0.9500	C37—H37	0.9500
C18—C19	1.415 (4)	C38—C39	1.412 (4)
C18—H18	0.9500	C38—H38	0.9500
C19—O2	1.346 (3)	C39—O4	1.354 (3)
C20—O2	1.440 (3)	C40—O4	1.437 (3)
C20—H20A	0.9900	C40—H40A	0.9900
C20—H20B	0.9900	C40—H40B	0.9900
C6—C1—C2	118.4 (3)	C26—C21—C27	117.9 (3)
C6—C1—C7	123.1 (3)	C22—C21—C27	123.6 (3)
C2—C1—C7	118.4 (3)	C23—C22—C21	120.4 (3)
C3—C2—C1	120.8 (3)	C23—C22—H22	119.8
C3—C2—H2	119.6	C21—C22—H22	119.8
C1—C2—H2	119.6	C24—C23—C22	120.4 (3)
C2—C3—C4	120.4 (3)	C24—C23—H23	119.8
C2—C3—H3	119.8	C22—C23—H23	119.8
C4—C3—H3	119.8	C23—C24—C25	120.4 (4)
C5—C4—C3	119.6 (4)	C23—C24—H24	119.8
C5—C4—H4	120.2	C25—C24—H24	119.8
C3—C4—H4	120.2	C24—C25—C26	119.3 (3)
C4—C5—C6	120.7 (3)	C24—C25—H25	120.4
C4—C5—H5	119.6	C26—C25—H25	120.4
C6—C5—H5	119.6	C25—C26—C21	121.1 (3)
C5—C6—C1	120.0 (3)	C25—C26—H26	119.4
C5—C6—H6	120.0	C21—C26—H26	119.4
C1—C6—H6	120.0	C28—C27—C21	130.3 (3)
C8—C7—C1	129.9 (3)	C28—C27—H27	114.8
C8—C7—H7	115.1	C21—C27—H27	114.8
C1—C7—H7	115.1	C27—C28—C29	118.1 (3)
C7—C8—C20	125.0 (3)	C27—C28—C40	125.9 (3)
C7—C8—C9	118.6 (2)	C29—C28—C40	115.9 (3)
C20—C8—C9	116.5 (3)	O3—C29—C30	123.1 (3)
O1—C9—C10	123.0 (3)	O3—C29—C28	120.6 (3)
O1—C9—C8	120.7 (3)	C30—C29—C28	116.2 (3)
C10—C9—C8	116.2 (3)	C39—C30—C31	117.8 (3)
C19—C10—C11	117.8 (3)	C39—C30—C29	118.2 (3)
C19—C10—C9	118.1 (3)	C31—C30—C29	123.5 (3)
C11—C10—C9	123.7 (3)	C32—C31—C36	117.0 (3)
C12—C11—C16	117.3 (3)	C32—C31—C30	123.7 (3)
C12—C11—C10	123.8 (3)	C36—C31—C30	119.3 (3)
C16—C11—C10	118.9 (3)	C33—C32—C31	121.1 (3)
C13—C12—C11	121.6 (3)	C33—C32—H32	119.4
C13—C12—H12	119.2	C31—C32—H32	119.4
C11—C12—H12	119.2	C32—C33—C34	121.4 (3)
C12—C13—C14	120.7 (3)	C32—C33—H33	119.3
C12—C13—H13	119.6	C34—C33—H33	119.3
C14—C13—H13	119.6	C35—C34—C33	119.1 (3)
C15—C14—C13	119.4 (3)	C35—C34—H34	120.5
C15—C14—H14	120.3	C33—C34—H34	120.5
C13—C14—H14	120.3	C34—C35—C36	121.4 (3)
C14—C15—C16	121.5 (3)	C34—C35—H35	119.3
C14—C15—H15	119.2	C36—C35—H35	119.3
C16—C15—H15	119.2	C35—C36—C37	120.7 (3)
C15—C16—C17	120.7 (3)	C35—C36—C31	120.0 (3)
C15—C16—C11	119.4 (3)	C37—C36—C31	119.3 (3)
C17—C16—C11	119.9 (3)	C38—C37—C36	121.4 (3)
C18—C17—C16	121.1 (3)	C38—C37—H37	119.3
C18—C17—H17	119.5	C36—C37—H37	119.3
C16—C17—H17	119.5	C37—C38—C39	119.3 (3)
C17—C18—C19	120.0 (3)	C37—C38—H38	120.3
C17—C18—H18	120.0	C39—C38—H38	120.3
C19—C18—H18	120.0	O4—C39—C30	123.8 (3)
O2—C19—C10	124.6 (3)	O4—C39—C38	113.4 (2)
O2—C19—C18	113.0 (2)	C30—C39—C38	122.7 (3)
C10—C19—C18	122.3 (3)	O4—C40—C28	112.3 (2)
O2—C20—C8	112.7 (2)	O4—C40—H40A	109.1
O2—C20—H20A	109.1	C28—C40—H40A	109.1
C8—C20—H20A	109.1	O4—C40—H40B	109.1
O2—C20—H20B	109.1	C28—C40—H40B	109.1
C8—C20—H20B	109.1	H40A—C40—H40B	107.9
H20A—C20—H20B	107.8	C19—O2—C20	116.7 (2)
C26—C21—C22	118.4 (3)	C39—O4—C40	116.3 (2)
C6—C1—C2—C3	−1.6 (4)	C22—C23—C24—C25	−0.9 (5)
C7—C1—C2—C3	178.8 (3)	C23—C24—C25—C26	1.0 (5)
C1—C2—C3—C4	0.1 (5)	C24—C25—C26—C21	−1.8 (4)
C2—C3—C4—C5	1.3 (5)	C22—C21—C26—C25	2.3 (4)
C3—C4—C5—C6	−1.2 (5)	C27—C21—C26—C25	179.9 (3)
C4—C5—C6—C1	−0.3 (5)	C26—C21—C27—C28	152.6 (3)
C2—C1—C6—C5	1.7 (5)	C22—C21—C27—C28	−30.0 (5)
C7—C1—C6—C5	−178.8 (3)	C21—C27—C28—C29	179.2 (3)
C6—C1—C7—C8	32.2 (5)	C21—C27—C28—C40	−0.7 (6)
C2—C1—C7—C8	−148.3 (4)	C27—C28—C29—O3	−7.9 (5)
C1—C7—C8—C20	−0.2 (6)	C40—C28—C29—O3	172.0 (3)
C1—C7—C8—C9	179.2 (3)	C27—C28—C29—C30	167.8 (3)
C7—C8—C9—O1	9.3 (5)	C40—C28—C29—C30	−12.3 (4)
C20—C8—C9—O1	−171.2 (3)	O3—C29—C30—C39	162.2 (3)
C7—C8—C9—C10	−166.3 (3)	C28—C29—C30—C39	−13.4 (4)
C20—C8—C9—C10	13.1 (4)	O3—C29—C30—C31	−8.8 (5)
O1—C9—C10—C19	−165.1 (3)	C28—C29—C30—C31	175.6 (3)
C8—C9—C10—C19	10.4 (4)	C39—C30—C31—C32	175.3 (3)
O1—C9—C10—C11	7.2 (5)	C29—C30—C31—C32	−13.7 (5)
C8—C9—C10—C11	−177.2 (3)	C39—C30—C31—C36	−4.4 (5)
C19—C10—C11—C12	−177.7 (3)	C29—C30—C31—C36	166.6 (3)
C9—C10—C11—C12	10.0 (5)	C36—C31—C32—C33	−0.7 (5)
C19—C10—C11—C16	1.9 (5)	C30—C31—C32—C33	179.6 (3)
C9—C10—C11—C16	−170.4 (3)	C31—C32—C33—C34	−1.5 (5)
C16—C11—C12—C13	0.0 (5)	C32—C33—C34—C35	2.5 (5)
C10—C11—C12—C13	179.6 (3)	C33—C34—C35—C36	−1.4 (5)
C11—C12—C13—C14	1.4 (5)	C34—C35—C36—C37	179.5 (3)
C12—C13—C14—C15	−1.3 (5)	C34—C35—C36—C31	−0.7 (5)
C13—C14—C15—C16	−0.1 (5)	C32—C31—C36—C35	1.7 (5)
C14—C15—C16—C17	179.8 (3)	C30—C31—C36—C35	−178.5 (3)
C14—C15—C16—C11	1.5 (5)	C32—C31—C36—C37	−178.5 (3)
C12—C11—C16—C15	−1.4 (5)	C30—C31—C36—C37	1.3 (5)
C10—C11—C16—C15	179.0 (3)	C35—C36—C37—C38	−178.6 (3)
C12—C11—C16—C17	−179.7 (3)	C31—C36—C37—C38	1.6 (4)
C10—C11—C16—C17	0.7 (5)	C36—C37—C38—C39	−1.3 (4)
C15—C16—C17—C18	179.5 (3)	C31—C30—C39—O4	−178.7 (3)
C11—C16—C17—C18	−2.2 (5)	C29—C30—C39—O4	9.8 (4)
C16—C17—C18—C19	1.0 (4)	C31—C30—C39—C38	5.0 (4)
C11—C10—C19—O2	−179.9 (3)	C29—C30—C39—C38	−166.5 (3)
C9—C10—C19—O2	−7.1 (4)	C37—C38—C39—O4	−178.8 (3)
C11—C10—C19—C18	−3.2 (4)	C37—C38—C39—C30	−2.1 (4)
C9—C10—C19—C18	169.6 (3)	C27—C28—C40—O4	−138.8 (3)
C17—C18—C19—O2	178.8 (3)	C29—C28—C40—O4	41.4 (4)
C17—C18—C19—C10	1.8 (4)	C10—C19—O2—C20	−21.3 (4)
C7—C8—C20—O2	139.9 (3)	C18—C19—O2—C20	161.7 (2)
C9—C8—C20—O2	−39.5 (4)	C8—C20—O2—C19	43.8 (4)
C26—C21—C22—C23	−2.2 (4)	C30—C39—O4—C40	21.4 (4)
C27—C21—C22—C23	−179.6 (3)	C38—C39—O4—C40	−161.9 (2)
C21—C22—C23—C24	1.5 (5)	C28—C40—O4—C39	−46.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.95	2.38	2.770 (4)	104
C12—H12···O1	0.95	2.22	2.856 (4)	123
C27—H27···O3	0.95	2.35	2.755 (4)	105
C32—H32···O3	0.95	2.25	2.857 (4)	121
C20—H20A···Cg2^i	0.99	2.90	3.735 (3)	143
C38—H38···Cg1	0.95	2.89	3.739 (3)	149

Symmetry code: (i) x−1/2, −y, z.