2-(5-Isopropyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

There are two mol-ecules in the asymmetric unit of the title compound, C(14)H(16)O(3)S. In the crystal structure, the carboxyl groups are involved in inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers. These dimers are further packed into stacks along the a axis by aromatic π-π inter-actions between the furan rings of adjacent mol-ecules [centroid-centroid distance = 3.430 (4) Å] and by additional C-H⋯π and C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 2-(3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2009 ▶); Seo et al. (2007 ▶). For the biological and pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Ward (1997 ▶).

Experimental

Crystal data

C14H16O3S

M = 264.33

Monoclinic,

a = 17.160 (2) Å

b = 8.7773 (7) Å

c = 17.819 (2) Å

β = 93.905 (2)°

V = 2677.6 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

19182 measured reflections

4727 independent reflections

3284 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.139

S = 1.09

4727 reflections

336 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021242/wm2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021242/wm2239Isup2.hkl

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

C14H16O3S	F(000) = 1120
Mr = 264.33	Dx = 1.311 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5245 reflections
a = 17.160 (2) Å	θ = 2.4–28.0°
b = 8.7773 (7) Å	µ = 0.24 mm−1
c = 17.819 (2) Å	T = 173 K
β = 93.905 (2)°	Block, colorless
V = 2677.6 (5) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker SMART CCD diffractometer	3284 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
graphite	θmax = 25.0°, θmin = 1.2°
Detector resolution: 10.0 pixels mm-1	h = −20→20
φ and ω scans	k = −10→10
19182 measured reflections	l = −21→20
4727 independent 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)] = 0.052	Hydrogen site location: difference Fourier map
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0613P)2 + 1.3164P] where P = (Fo2 + 2Fc2)/3
4727 reflections	(Δ/σ)max < 0.001
336 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.24 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
S1	0.37862 (4)	0.80938 (8)	0.21890 (4)	0.0331 (2)
S2	0.12907 (4)	0.14800 (8)	0.26676 (5)	0.0351 (2)
O1	0.33687 (10)	0.3877 (2)	0.28508 (10)	0.0279 (5)
O3	0.46953 (11)	0.4873 (3)	0.40822 (11)	0.0375 (5)
O2	0.41120 (12)	0.6069 (3)	0.50141 (12)	0.0371 (6)
H2O	0.449 (2)	0.570 (5)	0.530 (2)	0.076 (14)*
O4	0.15963 (10)	0.5807 (2)	0.21373 (11)	0.0284 (5)
O6	0.02448 (11)	0.4616 (3)	0.09349 (11)	0.0416 (6)
O5	0.09385 (13)	0.4311 (3)	−0.00875 (13)	0.0385 (6)
H5O	0.063 (3)	0.459 (5)	−0.037 (2)	0.090 (18)*
C1	0.36056 (14)	0.6137 (3)	0.22892 (15)	0.0225 (6)
C2	0.35460 (14)	0.4999 (3)	0.16827 (15)	0.0230 (6)
C3	0.36002 (15)	0.4995 (3)	0.08765 (16)	0.0261 (6)
H3	0.3698	0.5919	0.0622	0.031*
C4	0.35082 (15)	0.3625 (3)	0.04656 (16)	0.0289 (7)
C5	0.33688 (16)	0.2281 (3)	0.08780 (18)	0.0332 (7)
H5	0.3310	0.1346	0.0611	0.040*
C6	0.33120 (16)	0.2260 (3)	0.16803 (17)	0.0333 (7)
H6	0.3217	0.1342	0.1941	0.040*
C7	0.34024 (14)	0.3644 (3)	0.20579 (15)	0.0250 (6)
C8	0.34931 (14)	0.5411 (3)	0.29642 (16)	0.0248 (6)
C9	0.34748 (15)	0.5971 (3)	0.37775 (15)	0.0287 (7)
H9A	0.3422	0.7094	0.3768	0.034*
H9B	0.3000	0.5555	0.3988	0.034*
C10	0.41644 (15)	0.5572 (3)	0.43041 (15)	0.0244 (6)
C11	0.35236 (17)	0.3567 (4)	−0.04190 (17)	0.0357 (7)
H11	0.3469	0.2475	−0.0574	0.043*
C12	0.28631 (18)	0.4423 (4)	−0.08121 (18)	0.0476 (9)
H12A	0.2894	0.5498	−0.0665	0.057*
H12B	0.2366	0.3994	−0.0672	0.057*
H12C	0.2896	0.4338	−0.1357	0.057*
C13	0.42626 (19)	0.4145 (5)	−0.07065 (19)	0.0541 (10)
H13A	0.4703	0.3543	−0.0490	0.065*
H13B	0.4335	0.5216	−0.0563	0.065*
H13C	0.4236	0.4057	−0.1256	0.065*
C15	0.14263 (14)	0.3457 (3)	0.26341 (15)	0.0248 (6)
C16	0.14678 (14)	0.4533 (3)	0.32748 (15)	0.0227 (6)
C17	0.14295 (15)	0.4436 (3)	0.40849 (16)	0.0288 (7)
H17	0.1367	0.3472	0.4316	0.035*
C18	0.14835 (16)	0.5757 (3)	0.45287 (17)	0.0303 (7)
C19	0.15631 (15)	0.7170 (3)	0.41529 (17)	0.0322 (7)
H19	0.1585	0.8077	0.4444	0.039*
C20	0.16123 (16)	0.7293 (3)	0.33547 (18)	0.0323 (7)
H20	0.1674	0.8253	0.3120	0.039*
C21	0.15664 (14)	0.5951 (3)	0.29375 (16)	0.0250 (6)
C22	0.15112 (14)	0.4274 (3)	0.19790 (16)	0.0263 (6)
C23	0.15319 (15)	0.3839 (3)	0.11477 (16)	0.0312 (7)
H23A	0.2005	0.4296	0.0952	0.037*
H23B	0.1587	0.2718	0.1115	0.037*
C24	0.08450 (15)	0.4305 (3)	0.06474 (16)	0.0262 (6)
C25	0.14598 (19)	0.5682 (4)	0.54135 (18)	0.0416 (8)
H25	0.1474	0.4582	0.5560	0.050*
C26	0.0728 (2)	0.6345 (5)	0.5684 (2)	0.0606 (11)
H26A	0.0275	0.5798	0.5453	0.073*
H26B	0.0693	0.7424	0.5545	0.073*
H26C	0.0736	0.6249	0.6233	0.073*
C27	0.21352 (19)	0.6445 (5)	0.58342 (19)	0.0536 (10)
H27A	0.2141	0.7528	0.5701	0.064*
H27B	0.2623	0.5966	0.5702	0.064*
H27C	0.2084	0.6340	0.6376	0.064*
C28	0.02834 (17)	0.1368 (4)	0.2460 (2)	0.0464 (9)
H28A	0.0014	0.1957	0.2832	0.070*
H28B	0.0117	0.0301	0.2476	0.070*
H28C	0.0153	0.1785	0.1957	0.070*
C14	0.47646 (16)	0.8192 (4)	0.25281 (19)	0.0407 (8)
H14A	0.4813	0.7860	0.3054	0.061*
H14B	0.4950	0.9245	0.2494	0.061*
H14C	0.5079	0.7528	0.2226	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0323 (4)	0.0251 (4)	0.0406 (5)	−0.0001 (3)	−0.0085 (3)	0.0003 (3)
S2	0.0312 (4)	0.0236 (4)	0.0487 (5)	0.0013 (3)	−0.0087 (3)	−0.0014 (3)
O1	0.0218 (10)	0.0294 (11)	0.0320 (11)	−0.0009 (8)	−0.0012 (8)	0.0058 (9)
O3	0.0219 (11)	0.0604 (15)	0.0296 (12)	0.0138 (10)	−0.0040 (9)	−0.0077 (10)
O2	0.0271 (11)	0.0563 (15)	0.0272 (12)	0.0128 (10)	−0.0046 (9)	−0.0069 (10)
O4	0.0240 (10)	0.0284 (11)	0.0325 (12)	−0.0012 (8)	−0.0002 (8)	0.0051 (9)
O6	0.0213 (11)	0.0693 (16)	0.0338 (12)	0.0094 (10)	−0.0006 (9)	−0.0044 (11)
O5	0.0249 (12)	0.0597 (16)	0.0307 (13)	0.0043 (10)	0.0001 (10)	0.0029 (11)
C1	0.0138 (12)	0.0261 (15)	0.0268 (16)	0.0015 (11)	−0.0037 (11)	−0.0003 (12)
C2	0.0116 (12)	0.0262 (15)	0.0307 (16)	0.0006 (11)	−0.0025 (11)	−0.0007 (12)
C3	0.0181 (13)	0.0282 (16)	0.0318 (17)	−0.0002 (11)	0.0002 (12)	0.0027 (13)
C4	0.0149 (13)	0.0359 (17)	0.0358 (17)	0.0032 (12)	0.0012 (12)	−0.0073 (14)
C5	0.0254 (15)	0.0276 (16)	0.046 (2)	0.0036 (12)	−0.0002 (14)	−0.0101 (14)
C6	0.0292 (16)	0.0230 (16)	0.047 (2)	0.0012 (12)	−0.0022 (14)	0.0032 (14)
C7	0.0143 (13)	0.0310 (16)	0.0292 (16)	0.0019 (11)	−0.0016 (11)	0.0034 (13)
C8	0.0139 (13)	0.0257 (15)	0.0343 (17)	0.0028 (11)	−0.0024 (11)	−0.0022 (12)
C9	0.0180 (14)	0.0401 (18)	0.0277 (16)	0.0056 (12)	−0.0008 (12)	0.0004 (13)
C10	0.0204 (14)	0.0287 (16)	0.0243 (16)	−0.0009 (12)	0.0027 (12)	0.0000 (12)
C11	0.0315 (16)	0.0401 (18)	0.0355 (18)	0.0025 (14)	0.0013 (13)	−0.0109 (15)
C12	0.0338 (18)	0.077 (3)	0.0315 (19)	0.0059 (17)	−0.0015 (14)	−0.0036 (17)
C13	0.0362 (19)	0.089 (3)	0.038 (2)	−0.0022 (19)	0.0099 (16)	−0.0099 (19)
C15	0.0141 (13)	0.0265 (15)	0.0331 (16)	0.0025 (11)	−0.0024 (11)	0.0008 (13)
C16	0.0091 (12)	0.0248 (15)	0.0339 (16)	0.0004 (10)	−0.0011 (11)	0.0015 (12)
C17	0.0212 (14)	0.0282 (16)	0.0371 (18)	−0.0008 (11)	0.0013 (12)	0.0053 (13)
C18	0.0217 (14)	0.0314 (17)	0.0377 (18)	0.0001 (12)	0.0020 (13)	−0.0014 (14)
C19	0.0241 (15)	0.0283 (16)	0.0438 (19)	0.0030 (12)	0.0005 (13)	−0.0100 (14)
C20	0.0277 (15)	0.0182 (15)	0.051 (2)	0.0005 (12)	−0.0010 (14)	0.0018 (13)
C21	0.0143 (13)	0.0262 (15)	0.0344 (17)	−0.0004 (11)	−0.0001 (11)	0.0042 (13)
C22	0.0130 (13)	0.0274 (15)	0.0379 (17)	0.0021 (11)	−0.0031 (12)	0.0002 (13)
C23	0.0212 (14)	0.0380 (18)	0.0341 (17)	0.0064 (12)	−0.0005 (12)	−0.0018 (14)
C24	0.0222 (15)	0.0285 (16)	0.0282 (17)	−0.0007 (12)	0.0038 (12)	−0.0030 (12)
C25	0.056 (2)	0.0343 (19)	0.0361 (19)	0.0008 (15)	0.0111 (16)	−0.0042 (15)
C26	0.044 (2)	0.088 (3)	0.052 (2)	−0.018 (2)	0.0202 (18)	−0.017 (2)
C27	0.043 (2)	0.078 (3)	0.039 (2)	0.0160 (19)	−0.0024 (16)	−0.0119 (19)
C28	0.0313 (17)	0.043 (2)	0.066 (2)	−0.0109 (15)	0.0088 (16)	−0.0017 (17)
C14	0.0276 (16)	0.047 (2)	0.048 (2)	−0.0114 (14)	0.0016 (14)	−0.0024 (16)

S1—C14	1.747 (3)	C12—H12C	0.9800
S1—C1	1.757 (3)	C13—H13A	0.9800
S2—C28	1.745 (3)	C13—H13B	0.9800
S2—C15	1.752 (3)	C13—H13C	0.9800
O1—C8	1.377 (3)	C15—C22	1.387 (4)
O1—C7	1.432 (3)	C15—C16	1.480 (4)
O3—C10	1.188 (3)	C16—C21	1.398 (4)
O2—C10	1.347 (3)	C16—C17	1.452 (4)
O2—H2O	0.86 (4)	C17—C18	1.403 (4)
O4—C22	1.380 (3)	C17—H17	0.9500
O4—C21	1.436 (3)	C18—C19	1.421 (4)
O6—C24	1.212 (3)	C18—C25	1.581 (4)
O5—C24	1.330 (3)	C19—C20	1.435 (4)
O5—H5O	0.75 (4)	C19—H19	0.9500
C1—C8	1.386 (4)	C20—C21	1.392 (4)
C1—C2	1.470 (4)	C20—H20	0.9500
C2—C7	1.394 (4)	C22—C23	1.533 (4)
C2—C3	1.446 (4)	C23—C24	1.486 (4)
C3—C4	1.411 (4)	C23—H23A	0.9900
C3—H3	0.9500	C23—H23B	0.9900
C4—C5	1.419 (4)	C25—C26	1.493 (5)
C4—C11	1.579 (4)	C25—C27	1.495 (5)
C5—C6	1.440 (4)	C25—H25	1.0000
C5—H5	0.9500	C26—H26A	0.9800
C6—C7	1.392 (4)	C26—H26B	0.9800
C6—H6	0.9500	C26—H26C	0.9800
C8—C9	1.532 (4)	C27—H27A	0.9800
C9—C10	1.501 (4)	C27—H27B	0.9800
C9—H9A	0.9900	C27—H27C	0.9800
C9—H9B	0.9900	C28—H28A	0.9800
C11—C13	1.489 (4)	C28—H28B	0.9800
C11—C12	1.494 (4)	C28—H28C	0.9800
C11—H11	1.0000	C14—H14A	0.9800
C12—H12A	0.9800	C14—H14B	0.9800
C12—H12B	0.9800	C14—H14C	0.9800
C14—S1—C1	100.68 (14)	C21—C16—C17	119.6 (2)
C28—S2—C15	100.39 (14)	C21—C16—C15	103.7 (2)
C8—O1—C7	105.5 (2)	C17—C16—C15	136.6 (2)
C10—O2—H2O	110 (3)	C18—C17—C16	120.4 (3)
C22—O4—C21	106.2 (2)	C18—C17—H17	119.8
C24—O5—H5O	123 (4)	C16—C17—H17	119.8
C8—C1—C2	108.6 (2)	C17—C18—C19	117.4 (3)
C8—C1—S1	125.0 (2)	C17—C18—C25	121.5 (3)
C2—C1—S1	126.4 (2)	C19—C18—C25	121.1 (3)
C7—C2—C3	120.0 (2)	C18—C19—C20	123.2 (3)
C7—C2—C1	103.4 (2)	C18—C19—H19	118.4
C3—C2—C1	136.6 (2)	C20—C19—H19	118.4
C4—C3—C2	120.4 (3)	C21—C20—C19	117.4 (3)
C4—C3—H3	119.8	C21—C20—H20	121.3
C2—C3—H3	119.8	C19—C20—H20	121.3
C3—C4—C5	117.2 (3)	C20—C21—C16	121.9 (3)
C3—C4—C11	122.5 (3)	C20—C21—O4	126.9 (2)
C5—C4—C11	120.3 (3)	C16—C21—O4	111.2 (2)
C4—C5—C6	123.4 (3)	O4—C22—C15	110.4 (2)
C4—C5—H5	118.3	O4—C22—C23	115.6 (2)
C6—C5—H5	118.3	C15—C22—C23	134.0 (3)
C7—C6—C5	117.1 (3)	C24—C23—C22	116.2 (2)
C7—C6—H6	121.4	C24—C23—H23A	108.2
C5—C6—H6	121.4	C22—C23—H23A	108.2
C6—C7—C2	122.0 (3)	C24—C23—H23B	108.2
C6—C7—O1	126.2 (2)	C22—C23—H23B	108.2
C2—C7—O1	111.8 (2)	H23A—C23—H23B	107.4
O1—C8—C1	110.6 (2)	O6—C24—O5	125.3 (3)
O1—C8—C9	116.1 (2)	O6—C24—C23	118.1 (3)
C1—C8—C9	133.3 (3)	O5—C24—C23	116.6 (2)
C10—C9—C8	116.8 (2)	C26—C25—C27	107.7 (3)
C10—C9—H9A	108.1	C26—C25—C18	112.7 (3)
C8—C9—H9A	108.1	C27—C25—C18	114.2 (3)
C10—C9—H9B	108.1	C26—C25—H25	107.3
C8—C9—H9B	108.1	C27—C25—H25	107.3
H9A—C9—H9B	107.3	C18—C25—H25	107.3
O3—C10—O2	125.6 (3)	C25—C26—H26A	109.5
O3—C10—C9	120.2 (3)	C25—C26—H26B	109.5
O2—C10—C9	114.3 (2)	H26A—C26—H26B	109.5
C13—C11—C12	107.7 (3)	C25—C26—H26C	109.5
C13—C11—C4	113.9 (3)	H26A—C26—H26C	109.5
C12—C11—C4	112.8 (2)	H26B—C26—H26C	109.5
C13—C11—H11	107.4	C25—C27—H27A	109.5
C12—C11—H11	107.4	C25—C27—H27B	109.5
C4—C11—H11	107.4	H27A—C27—H27B	109.5
C11—C12—H12A	109.5	C25—C27—H27C	109.5
C11—C12—H12B	109.5	H27A—C27—H27C	109.5
H12A—C12—H12B	109.5	H27B—C27—H27C	109.5
C11—C12—H12C	109.5	S2—C28—H28A	109.5
H12A—C12—H12C	109.5	S2—C28—H28B	109.5
H12B—C12—H12C	109.5	H28A—C28—H28B	109.5
C11—C13—H13A	109.5	S2—C28—H28C	109.5
C11—C13—H13B	109.5	H28A—C28—H28C	109.5
H13A—C13—H13B	109.5	H28B—C28—H28C	109.5
C11—C13—H13C	109.5	S1—C14—H14A	109.5
H13A—C13—H13C	109.5	S1—C14—H14B	109.5
H13B—C13—H13C	109.5	H14A—C14—H14B	109.5
C22—C15—C16	108.5 (2)	S1—C14—H14C	109.5
C22—C15—S2	124.3 (2)	H14A—C14—H14C	109.5
C16—C15—S2	127.2 (2)	H14B—C14—H14C	109.5
C14—S1—C1—C8	75.9 (3)	C28—S2—C15—C22	−83.6 (3)
C14—S1—C1—C2	−104.3 (2)	C28—S2—C15—C16	96.2 (2)
C8—C1—C2—C7	−0.3 (3)	C22—C15—C16—C21	0.8 (3)
S1—C1—C2—C7	179.84 (19)	S2—C15—C16—C21	−178.99 (19)
C8—C1—C2—C3	179.8 (3)	C22—C15—C16—C17	−179.4 (3)
S1—C1—C2—C3	0.0 (4)	S2—C15—C16—C17	0.8 (4)
C7—C2—C3—C4	0.0 (4)	C21—C16—C17—C18	0.6 (4)
C1—C2—C3—C4	179.9 (3)	C15—C16—C17—C18	−179.1 (3)
C2—C3—C4—C5	−0.5 (4)	C16—C17—C18—C19	1.0 (4)
C2—C3—C4—C11	177.2 (2)	C16—C17—C18—C25	−178.8 (2)
C3—C4—C5—C6	0.6 (4)	C17—C18—C19—C20	−1.8 (4)
C11—C4—C5—C6	−177.1 (2)	C25—C18—C19—C20	178.0 (3)
C4—C5—C6—C7	−0.2 (4)	C18—C19—C20—C21	1.0 (4)
C5—C6—C7—C2	−0.3 (4)	C19—C20—C21—C16	0.7 (4)
C5—C6—C7—O1	−179.9 (2)	C19—C20—C21—O4	179.5 (2)
C3—C2—C7—C6	0.4 (4)	C17—C16—C21—C20	−1.5 (4)
C1—C2—C7—C6	−179.5 (2)	C15—C16—C21—C20	178.4 (2)
C3—C2—C7—O1	−180.0 (2)	C17—C16—C21—O4	179.5 (2)
C1—C2—C7—O1	0.1 (3)	C15—C16—C21—O4	−0.6 (3)
C8—O1—C7—C6	179.7 (3)	C22—O4—C21—C20	−178.7 (3)
C8—O1—C7—C2	0.1 (3)	C22—O4—C21—C16	0.3 (3)
C7—O1—C8—C1	−0.3 (3)	C21—O4—C22—C15	0.3 (3)
C7—O1—C8—C9	179.2 (2)	C21—O4—C22—C23	−179.5 (2)
C2—C1—C8—O1	0.4 (3)	C16—C15—C22—O4	−0.7 (3)
S1—C1—C8—O1	−179.74 (17)	S2—C15—C22—O4	179.11 (17)
C2—C1—C8—C9	−179.0 (3)	C16—C15—C22—C23	179.1 (3)
S1—C1—C8—C9	0.8 (4)	S2—C15—C22—C23	−1.1 (4)
O1—C8—C9—C10	73.6 (3)	O4—C22—C23—C24	−70.7 (3)
C1—C8—C9—C10	−107.0 (3)	C15—C22—C23—C24	109.6 (3)
C8—C9—C10—O3	1.0 (4)	C22—C23—C24—O6	−19.0 (4)
C8—C9—C10—O2	−178.9 (2)	C22—C23—C24—O5	162.5 (2)
C3—C4—C11—C13	59.0 (4)	C17—C18—C25—C26	−110.7 (3)
C5—C4—C11—C13	−123.4 (3)	C19—C18—C25—C26	69.5 (4)
C3—C4—C11—C12	−64.2 (4)	C17—C18—C25—C27	126.1 (3)
C5—C4—C11—C12	113.4 (3)	C19—C18—C25—C27	−53.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3i	0.86 (4)	1.79 (4)	2.649 (3)	174 (4)
O5—H5O···O6ii	0.75 (4)	1.88 (4)	2.621 (3)	170 (5)
C19—H19···O5iii	0.95	2.70	3.567 (4)	151
C9—H9B···Cg4	0.99	2.57	3.350 (4)	136
C23—H23A···Cg2	0.99	2.58	3.299 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3i	0.86 (4)	1.79 (4)	2.649 (3)	174 (4)
O5—H5O⋯O6ii	0.75 (4)	1.88 (4)	2.621 (3)	170 (5)
C19—H19⋯O5iii	0.95	2.70	3.567 (4)	151
C9—H9B⋯Cg4	0.99	2.57	3.350 (4)	136
C23—H23A⋯Cg2	0.99	2.58	3.299 (4)	129

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg4 are the centroids of the C2–C7 and C16-C21 benzene rings, respectively.