Crystal structure of 2,5-dimethyl-3-(2-methyl-phenyl-sulfon-yl)-1-benzo-furan.

The title compound, C17H16O3S, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angle between the benzo-furan ring system [r.m.s. deviation of 0.013 (1) for A and 0.009 (1) Å for B] and the 2-methyl-phenyl ring is 83.88 (5) for A and 86.94 (5)° for B. In the crystal, the B mol-ecules are linked into a chain along the b-axis direction by C-H⋯O hydrogen bonds. The A mol-ecules are connected on either side of this chain by further C-H⋯O hydrogen bonds. These chains are linked via C-H⋯π inter-actions, forming sheets parallel to (100). There are also very weak π-π inter-actions present [centroid-centroid distance = 3.925 (11) Å] involvingthe 2-methyl-phenyl rings of neighbouring A and B mol-ecules.

Related literature

For a related structure and background to benzo­furan deriv­atives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C17H16O3S

M = 300.36

Monoclinic,

a = 16.7338 (4) Å

b = 8.0646 (2) Å

c = 21.8195 (6) Å

β = 95.296 (1)°

V = 2932.00 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.58 × 0.37 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.879, T max = 0.950

27259 measured reflections

6773 independent reflections

5313 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.04

6773 reflections

385 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814022788/su5004sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022788/su5004Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814022788/su5004Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814022788/su5004fig1.tif

The mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

x y z x y z x y z x y z . DOI: 10.1107/S1600536814022788/su5004fig2.tif

A view of the C—H⋯O inter­actions (dashed lines) in the crystal structure of the title compound - see Table 1 for details. H atoms not involved in hydrogen bonding have been omitted for clarity [Symmetry codes: (i) −x, y + , −z + ; (ii) x, y + 1, z; (iii) −x, y − , −z + ; (iv) x, y − 1, z].

Click here for additional data file.

x y z x y z . DOI: 10.1107/S1600536814022788/su5004fig3.tif

A view of the C—H⋯π and π–π inter­actions (dashed lines) in the crystal structure of the title compound - see Table 1 for details. H atoms non-participating in hydrogen-bonding have been omitted for clarity [Symmetry codes: (i) x, −y + , z − ; (ii) x, −y + , z + ].

CCDC reference: 1029621

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H16O3S	F(000) = 1264
Mr = 300.36	Dx = 1.361 Mg m−3
Monoclinic, P21/c	Melting point = 386–385 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.7338 (4) Å	Cell parameters from 5209 reflections
b = 8.0646 (2) Å	θ = 2.3–26.6°
c = 21.8195 (6) Å	µ = 0.23 mm−1
β = 95.296 (1)°	T = 173 K
V = 2932.00 (13) Å3	Block, colourless
Z = 8	0.58 × 0.37 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	6773 independent reflections
Radiation source: rotating anode	5313 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.042
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.9°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→10
Tmin = 0.879, Tmax = 0.950	l = −23→28
27259 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.056P)2 + 1.1004P] where P = (Fo2 + 2Fc2)/3
6773 reflections	(Δ/σ)max = 0.001
385 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.25 (d, J=7.52 Hz, 1H), 7.37-7.48 (m, 3H), 7.30 (d, J=8.52 Hz, 1H), 7.26 (d, J=7.52 Hz, 1H), 7.08 (d, J=8.56 Hz, 1H), 2.74 (s, 3H), 2.52 (s, 3H), 2.37 (s, 3H).

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
S1	0.29003 (3)	0.10514 (6)	0.48076 (2)	0.02658 (12)
O3	0.28718 (8)	−0.06396 (16)	0.50124 (6)	0.0361 (3)
O1	0.51121 (7)	0.27240 (17)	0.48421 (6)	0.0336 (3)
O2	0.26309 (8)	0.14295 (19)	0.41824 (6)	0.0388 (3)
C1	0.38848 (10)	0.1730 (2)	0.49575 (8)	0.0257 (4)
C2	0.43612 (10)	0.1551 (2)	0.55426 (8)	0.0245 (4)
C3	0.42259 (10)	0.0982 (2)	0.61259 (8)	0.0261 (4)
H3	0.3718	0.0542	0.6201	0.031*
C4	0.48413 (11)	0.1065 (2)	0.65957 (9)	0.0306 (4)
C5	0.55882 (11)	0.1708 (3)	0.64695 (9)	0.0356 (4)
H5	0.6008	0.1757	0.6794	0.043*
C6	0.57388 (11)	0.2272 (3)	0.58951 (10)	0.0355 (4)
H6	0.6249	0.2694	0.5815	0.043*
C7	0.51090 (10)	0.2191 (2)	0.54429 (8)	0.0285 (4)
C8	0.43609 (11)	0.2433 (2)	0.45585 (8)	0.0302 (4)
C9	0.47128 (13)	0.0478 (3)	0.72362 (9)	0.0427 (5)
H9A	0.4165	0.0746	0.7327	0.064*
H9B	0.5097	0.1032	0.7535	0.064*
H9C	0.4794	−0.0724	0.7262	0.064*
C10	0.42443 (13)	0.2938 (3)	0.39015 (9)	0.0404 (5)
H10A	0.4554	0.2202	0.3656	0.061*
H10B	0.4428	0.4083	0.3860	0.061*
H10C	0.3674	0.2863	0.3756	0.061*
C11	0.23229 (9)	0.2235 (2)	0.52923 (8)	0.0232 (3)
C12	0.19580 (10)	0.1353 (2)	0.57375 (8)	0.0283 (4)
H12	0.2052	0.0196	0.5784	0.034*
C13	0.14589 (11)	0.2152 (3)	0.61129 (9)	0.0337 (4)
H13	0.1211	0.1553	0.6419	0.040*
C14	0.13262 (11)	0.3823 (3)	0.60383 (9)	0.0351 (4)
H14	0.0978	0.4381	0.6290	0.042*
C15	0.16958 (11)	0.4699 (2)	0.55985 (9)	0.0330 (4)
H15	0.1597	0.5856	0.5557	0.040*
C16	0.22088 (10)	0.3944 (2)	0.52148 (8)	0.0265 (4)
C17	0.26127 (12)	0.4981 (3)	0.47580 (9)	0.0373 (5)
H17A	0.2446	0.6140	0.4790	0.056*
H17B	0.2458	0.4575	0.4341	0.056*
H17C	0.3196	0.4901	0.4846	0.056*
S2	0.22038 (3)	0.67798 (6)	0.26437 (2)	0.02693 (12)
O4	0.00302 (8)	0.83199 (19)	0.28806 (7)	0.0422 (4)
O5	0.22026 (8)	0.51558 (16)	0.23717 (7)	0.0360 (3)
O6	0.25599 (8)	0.69703 (19)	0.32615 (6)	0.0404 (4)
C29	0.27854 (10)	0.9817 (2)	0.22581 (8)	0.0272 (4)
C18	0.12153 (10)	0.7450 (2)	0.26076 (8)	0.0271 (4)
C19	0.06680 (10)	0.7498 (2)	0.20564 (8)	0.0263 (4)
C20	0.07067 (10)	0.7165 (2)	0.14330 (8)	0.0282 (4)
H20	0.1190	0.6767	0.1289	0.034*
C21	0.00326 (11)	0.7420 (2)	0.10269 (10)	0.0365 (5)
C22	−0.06806 (12)	0.7977 (3)	0.12514 (12)	0.0471 (6)
H22	−0.1141	0.8136	0.0969	0.057*
C23	−0.07384 (12)	0.8299 (3)	0.18648 (12)	0.0454 (6)
H23	−0.1225	0.8669	0.2012	0.054*
C24	−0.00521 (11)	0.8056 (2)	0.22530 (10)	0.0352 (4)
C25	0.08057 (12)	0.7949 (3)	0.30844 (9)	0.0365 (5)
C26	0.00614 (15)	0.7143 (3)	0.03466 (10)	0.0534 (6)
H26A	0.0072	0.8216	0.0137	0.080*
H26B	−0.0414	0.6520	0.0184	0.080*
H26C	0.0545	0.6514	0.0276	0.080*
C27	0.10147 (16)	0.8167 (3)	0.37561 (10)	0.0534 (6)
H27A	0.0772	0.7273	0.3980	0.080*
H27B	0.0811	0.9238	0.3886	0.080*
H27C	0.1599	0.8135	0.3846	0.080*
C28	0.26882 (10)	0.8114 (2)	0.21492 (8)	0.0235 (4)
C30	0.32432 (11)	1.0681 (2)	0.18626 (9)	0.0321 (4)
H30	0.3325	1.1837	0.1924	0.038*
C31	0.35822 (11)	0.9915 (3)	0.13847 (9)	0.0339 (4)
H31	0.3903	1.0539	0.1131	0.041*
C32	0.34591 (11)	0.8247 (3)	0.12726 (9)	0.0345 (4)
H32	0.3680	0.7725	0.0936	0.041*
C33	0.30100 (10)	0.7347 (2)	0.16561 (8)	0.0290 (4)
H33	0.2920	0.6197	0.1583	0.035*
C34	0.24201 (15)	1.0720 (3)	0.27628 (10)	0.0453 (5)
H34A	0.2581	1.1889	0.2761	0.068*
H34B	0.2606	1.0223	0.3160	0.068*
H34C	0.1834	1.0641	0.2698	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.0259 (2)	0.0283 (2)	0.0256 (2)	−0.00190 (17)	0.00290 (17)	−0.00472 (18)
O3	0.0361 (7)	0.0248 (7)	0.0485 (8)	−0.0034 (6)	0.0094 (6)	−0.0059 (6)
O1	0.0275 (6)	0.0383 (8)	0.0366 (7)	−0.0025 (6)	0.0121 (6)	0.0011 (6)
O2	0.0379 (8)	0.0539 (9)	0.0241 (7)	−0.0015 (7)	0.0002 (6)	−0.0076 (6)
C1	0.0246 (8)	0.0262 (9)	0.0268 (9)	0.0009 (7)	0.0055 (7)	−0.0019 (7)
C2	0.0228 (8)	0.0204 (8)	0.0306 (9)	0.0022 (7)	0.0049 (7)	−0.0040 (7)
C3	0.0249 (8)	0.0248 (9)	0.0288 (9)	−0.0013 (7)	0.0041 (7)	0.0009 (7)
C4	0.0302 (9)	0.0274 (9)	0.0335 (10)	0.0026 (7)	−0.0015 (8)	−0.0010 (8)
C5	0.0281 (9)	0.0365 (11)	0.0406 (11)	0.0008 (8)	−0.0059 (8)	−0.0020 (9)
C6	0.0216 (9)	0.0370 (11)	0.0485 (12)	−0.0022 (8)	0.0055 (8)	−0.0028 (9)
C7	0.0257 (9)	0.0272 (9)	0.0337 (10)	0.0018 (7)	0.0085 (7)	−0.0020 (8)
C8	0.0308 (9)	0.0299 (10)	0.0309 (10)	0.0026 (8)	0.0086 (8)	−0.0025 (8)
C9	0.0441 (12)	0.0477 (13)	0.0345 (11)	−0.0005 (10)	−0.0063 (9)	0.0054 (10)
C10	0.0471 (12)	0.0446 (12)	0.0314 (11)	−0.0004 (10)	0.0138 (9)	0.0041 (9)
C11	0.0192 (8)	0.0286 (9)	0.0216 (8)	0.0003 (7)	0.0001 (6)	−0.0013 (7)
C12	0.0248 (9)	0.0302 (10)	0.0294 (9)	0.0003 (7)	0.0006 (7)	0.0031 (8)
C13	0.0291 (9)	0.0438 (12)	0.0292 (10)	−0.0006 (8)	0.0076 (8)	0.0038 (8)
C14	0.0286 (10)	0.0431 (12)	0.0341 (10)	0.0044 (8)	0.0048 (8)	−0.0092 (9)
C15	0.0308 (9)	0.0290 (10)	0.0386 (11)	0.0035 (8)	0.0006 (8)	−0.0033 (8)
C16	0.0235 (8)	0.0279 (9)	0.0275 (9)	−0.0015 (7)	−0.0018 (7)	−0.0006 (7)
C17	0.0418 (11)	0.0302 (10)	0.0401 (11)	−0.0007 (8)	0.0053 (9)	0.0076 (9)
S2	0.0236 (2)	0.0282 (2)	0.0292 (2)	−0.00071 (17)	0.00328 (17)	0.00437 (18)
O4	0.0341 (8)	0.0445 (9)	0.0512 (9)	0.0028 (6)	0.0212 (7)	−0.0050 (7)
O5	0.0304 (7)	0.0246 (7)	0.0543 (9)	0.0007 (5)	0.0106 (6)	0.0034 (6)
O6	0.0377 (8)	0.0534 (9)	0.0292 (7)	−0.0056 (7)	−0.0015 (6)	0.0109 (6)
C29	0.0284 (9)	0.0278 (9)	0.0249 (9)	−0.0003 (7)	−0.0010 (7)	−0.0017 (7)
C18	0.0247 (8)	0.0273 (9)	0.0301 (9)	−0.0007 (7)	0.0074 (7)	−0.0001 (7)
C19	0.0202 (8)	0.0223 (9)	0.0370 (10)	−0.0015 (7)	0.0059 (7)	−0.0001 (7)
C20	0.0236 (8)	0.0244 (9)	0.0366 (10)	−0.0011 (7)	0.0020 (7)	−0.0027 (8)
C21	0.0319 (10)	0.0284 (10)	0.0473 (12)	−0.0030 (8)	−0.0069 (9)	−0.0045 (9)
C22	0.0265 (10)	0.0380 (12)	0.0736 (16)	0.0032 (9)	−0.0128 (10)	−0.0057 (11)
C23	0.0207 (9)	0.0381 (12)	0.0781 (17)	0.0032 (8)	0.0084 (10)	−0.0052 (11)
C24	0.0269 (9)	0.0319 (10)	0.0483 (12)	−0.0003 (8)	0.0118 (9)	−0.0051 (9)
C25	0.0379 (11)	0.0358 (11)	0.0382 (11)	−0.0013 (9)	0.0157 (9)	0.0000 (9)
C26	0.0538 (14)	0.0554 (15)	0.0465 (13)	0.0008 (12)	−0.0190 (11)	−0.0091 (11)
C27	0.0671 (16)	0.0598 (16)	0.0365 (12)	0.0019 (13)	0.0226 (11)	−0.0050 (11)
C28	0.0190 (8)	0.0277 (9)	0.0234 (8)	−0.0006 (7)	0.0003 (6)	0.0015 (7)
C30	0.0334 (10)	0.0281 (10)	0.0339 (10)	−0.0045 (8)	−0.0009 (8)	0.0032 (8)
C31	0.0286 (9)	0.0390 (11)	0.0344 (10)	−0.0030 (8)	0.0050 (8)	0.0095 (8)
C32	0.0306 (10)	0.0407 (11)	0.0336 (10)	0.0030 (8)	0.0108 (8)	−0.0004 (9)
C33	0.0247 (9)	0.0280 (9)	0.0348 (10)	0.0019 (7)	0.0061 (7)	−0.0022 (8)
C34	0.0689 (15)	0.0323 (11)	0.0366 (11)	−0.0067 (10)	0.0157 (11)	−0.0113 (9)

S1—O2	1.4295 (14)	S2—O6	1.4309 (14)
S1—O3	1.4373 (14)	S2—O5	1.4378 (14)
S1—C1	1.7379 (18)	S2—C18	1.7351 (18)
S1—C11	1.7754 (17)	S2—C28	1.7719 (17)
O1—C8	1.369 (2)	O4—C25	1.366 (2)
O1—C7	1.380 (2)	O4—C24	1.380 (2)
C1—C8	1.357 (2)	C29—C30	1.392 (3)
C1—C2	1.449 (2)	C29—C28	1.401 (2)
C2—C7	1.389 (2)	C29—C34	1.497 (3)
C2—C3	1.391 (2)	C18—C25	1.358 (3)
C3—C4	1.386 (2)	C18—C19	1.443 (2)
C3—H3	0.9500	C19—C24	1.391 (2)
C4—C5	1.404 (3)	C19—C20	1.394 (2)
C4—C9	1.510 (3)	C20—C21	1.384 (2)
C5—C6	1.378 (3)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.405 (3)
C6—C7	1.377 (3)	C21—C26	1.506 (3)
C6—H6	0.9500	C22—C23	1.376 (3)
C8—C10	1.486 (3)	C22—H22	0.9500
C9—H9A	0.9800	C23—C24	1.377 (3)
C9—H9B	0.9800	C23—H23	0.9500
C9—H9C	0.9800	C25—C27	1.485 (3)
C10—H10A	0.9800	C26—H26A	0.9800
C10—H10B	0.9800	C26—H26B	0.9800
C10—H10C	0.9800	C26—H26C	0.9800
C11—C12	1.390 (2)	C27—H27A	0.9800
C11—C16	1.400 (3)	C27—H27B	0.9800
C12—C13	1.382 (3)	C27—H27C	0.9800
C12—H12	0.9500	C28—C33	1.392 (2)
C13—C14	1.373 (3)	C30—C31	1.378 (3)
C13—H13	0.9500	C30—H30	0.9500
C14—C15	1.383 (3)	C31—C32	1.379 (3)
C14—H14	0.9500	C31—H31	0.9500
C15—C16	1.393 (3)	C32—C33	1.382 (3)
C15—H15	0.9500	C32—H32	0.9500
C16—C17	1.508 (3)	C33—H33	0.9500
C17—H17A	0.9800	C34—H34A	0.9800
C17—H17B	0.9800	C34—H34B	0.9800
C17—H17C	0.9800	C34—H34C	0.9800
O2—S1—O3	118.85 (9)	O6—S2—O5	118.11 (9)
O2—S1—C1	108.81 (9)	O6—S2—C18	108.77 (9)
O3—S1—C1	107.34 (8)	O5—S2—C18	107.46 (8)
O2—S1—C11	108.22 (8)	O6—S2—C28	109.53 (8)
O3—S1—C11	106.82 (8)	O5—S2—C28	106.55 (8)
C1—S1—C11	106.09 (8)	C18—S2—C28	105.72 (8)
C8—O1—C7	106.99 (13)	C25—O4—C24	107.11 (14)
C8—C1—C2	107.39 (15)	C30—C29—C28	116.58 (17)
C8—C1—S1	127.81 (14)	C30—C29—C34	119.84 (17)
C2—C1—S1	124.73 (13)	C28—C29—C34	123.57 (17)
C7—C2—C3	119.39 (16)	C25—C18—C19	107.70 (16)
C7—C2—C1	104.81 (16)	C25—C18—S2	127.13 (15)
C3—C2—C1	135.76 (16)	C19—C18—S2	125.11 (13)
C4—C3—C2	119.23 (17)	C24—C19—C20	118.89 (17)
C4—C3—H3	120.4	C24—C19—C18	104.65 (16)
C2—C3—H3	120.4	C20—C19—C18	136.46 (16)
C3—C4—C5	119.14 (18)	C21—C20—C19	119.18 (17)
C3—C4—C9	120.67 (17)	C21—C20—H20	120.4
C5—C4—C9	120.19 (17)	C19—C20—H20	120.4
C6—C5—C4	122.77 (18)	C20—C21—C22	119.5 (2)
C6—C5—H5	118.6	C20—C21—C26	120.71 (19)
C4—C5—H5	118.6	C22—C21—C26	119.77 (19)
C7—C6—C5	116.35 (17)	C23—C22—C21	122.55 (19)
C7—C6—H6	121.8	C23—C22—H22	118.7
C5—C6—H6	121.8	C21—C22—H22	118.7
C6—C7—O1	126.59 (16)	C22—C23—C24	116.24 (19)
C6—C7—C2	123.11 (18)	C22—C23—H23	121.9
O1—C7—C2	110.30 (16)	C24—C23—H23	121.9
C1—C8—O1	110.52 (16)	C23—C24—O4	126.14 (18)
C1—C8—C10	134.49 (18)	C23—C24—C19	123.6 (2)
O1—C8—C10	114.99 (16)	O4—C24—C19	110.24 (17)
C4—C9—H9A	109.5	C18—C25—O4	110.29 (17)
C4—C9—H9B	109.5	C18—C25—C27	134.5 (2)
H9A—C9—H9B	109.5	O4—C25—C27	115.18 (17)
C4—C9—H9C	109.5	C21—C26—H26A	109.5
H9A—C9—H9C	109.5	C21—C26—H26B	109.5
H9B—C9—H9C	109.5	H26A—C26—H26B	109.5
C8—C10—H10A	109.5	C21—C26—H26C	109.5
C8—C10—H10B	109.5	H26A—C26—H26C	109.5
H10A—C10—H10B	109.5	H26B—C26—H26C	109.5
C8—C10—H10C	109.5	C25—C27—H27A	109.5
H10A—C10—H10C	109.5	C25—C27—H27B	109.5
H10B—C10—H10C	109.5	H27A—C27—H27B	109.5
C12—C11—C16	121.63 (16)	C25—C27—H27C	109.5
C12—C11—S1	116.08 (14)	H27A—C27—H27C	109.5
C16—C11—S1	122.22 (13)	H27B—C27—H27C	109.5
C13—C12—C11	120.27 (18)	C33—C28—C29	121.31 (16)
C13—C12—H12	119.9	C33—C28—S2	115.62 (14)
C11—C12—H12	119.9	C29—C28—S2	122.98 (14)
C14—C13—C12	119.17 (18)	C31—C30—C29	122.19 (18)
C14—C13—H13	120.4	C31—C30—H30	118.9
C12—C13—H13	120.4	C29—C30—H30	118.9
C13—C14—C15	120.40 (18)	C30—C31—C32	120.42 (18)
C13—C14—H14	119.8	C30—C31—H31	119.8
C15—C14—H14	119.8	C32—C31—H31	119.8
C14—C15—C16	122.23 (18)	C31—C32—C33	119.08 (18)
C14—C15—H15	118.9	C31—C32—H32	120.5
C16—C15—H15	118.9	C33—C32—H32	120.5
C15—C16—C11	116.27 (17)	C32—C33—C28	120.36 (18)
C15—C16—C17	119.56 (17)	C32—C33—H33	119.8
C11—C16—C17	124.15 (16)	C28—C33—H33	119.8
C16—C17—H17A	109.5	C29—C34—H34A	109.5
C16—C17—H17B	109.5	C29—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
C16—C17—H17C	109.5	C29—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O5i	0.95	2.52	3.431 (3)	162
C34—H34B···O2ii	0.98	2.43	3.137 (2)	129
C31—H31···Cg1ii	0.95	2.93	3.773 (3)	148
C14—H14···Cg2i	0.95	3.00	3.876 (3)	154

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of benzene rings C2C7 and C19C24, respectively.

DHA	DH	HA	D A	DHA
C23H23O5i	0.95	2.52	3.431(3)	162
C34H34BO2ii	0.98	2.43	3.137(2)	129
C31H31Cg1ii	0.95	2.93	3.773(3)	148
C14H14Cg2i	0.95	3.00	3.876(3)	154

Symmetry codes: (i) ; (ii) .