Methyl 2-(5-iodo-7-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)IO(4)S. In each mol-ecule, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene and furan ring [centroid-centroid distance = 3.866 (7) Å], and by inter-molecular C-H⋯π inter-actions and a sulfin-yl-sulfinyl inter-action [S⋯O = 3.025 (4) Å]. The crystal structure also exhibits weak inter-molecular C-H⋯O hydrogen bonds and two different I⋯O halogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-iodo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2008 ▶). For halogen bonding, see: Politzer et al. (2007 ▶). For carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C13H13IO4S

M = 392.19

Triclinic,

a = 7.5424 (4) Å

b = 11.2177 (6) Å

c = 17.845 (1) Å

α = 77.701 (1)°

β = 88.074 (1)°

γ = 88.229 (1)°

V = 1473.92 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.32 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.574, T max = 0.790

12617 measured reflections

6248 independent reflections

5328 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.088

S = 1.18

6248 reflections

349 parameters

H-atom parameters constrained

Δρmax = 1.15 e Å−3

Δρmin = −1.46 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/S1600536809016298/gw2062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016298/gw2062Isup2.hkl

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

C13H13IO4S	Z = 4
Mr = 392.19	F(000) = 768
Triclinic, P1	Dx = 1.767 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5424 (4) Å	Cell parameters from 6307 reflections
b = 11.2177 (6) Å	θ = 2.3–28.2°
c = 17.845 (1) Å	µ = 2.32 mm−1
α = 77.701 (1)°	T = 293 K
β = 88.074 (1)°	Block, colorless
γ = 88.229 (1)°	0.30 × 0.20 × 0.10 mm
V = 1473.92 (14) Å3

Bruker SMART CCD diffractometer	6248 independent reflections
Radiation source: fine-focus sealed tube	5328 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −14→14
Tmin = 0.574, Tmax = 0.790	l = −22→22
12617 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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F2) = 0.088	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0184P)2 + 4.3135P] where P = (Fo2 + 2Fc2)/3
6248 reflections	(Δ/σ)max < 0.001
349 parameters	Δρmax = 1.15 e Å−3
0 restraints	Δρmin = −1.46 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
I1	0.66948 (5)	−0.00958 (3)	0.780861 (19)	0.03974 (11)
S1	0.92033 (15)	0.36686 (11)	0.47095 (7)	0.0253 (3)
O1	0.7992 (4)	0.0463 (3)	0.43207 (17)	0.0234 (7)
O2	0.7940 (4)	0.2574 (3)	0.20886 (18)	0.0285 (8)
O3	0.6320 (5)	0.3131 (3)	0.30365 (19)	0.0340 (8)
O4	1.0056 (5)	0.3653 (3)	0.5448 (2)	0.0343 (8)
C1	0.8593 (6)	0.2142 (4)	0.4747 (3)	0.0210 (9)
C2	0.7987 (6)	0.1252 (4)	0.5400 (3)	0.0193 (9)
C3	0.7743 (6)	0.1181 (4)	0.6187 (3)	0.0217 (10)
H3	0.8012	0.1827	0.6411	0.026*
C4	0.7085 (6)	0.0108 (4)	0.6616 (3)	0.0226 (10)
C5	0.6671 (6)	−0.0880 (4)	0.6299 (3)	0.0249 (10)
H5	0.6212	−0.1579	0.6614	0.030*
C6	0.6938 (6)	−0.0833 (4)	0.5515 (3)	0.0260 (10)
C7	0.7615 (5)	0.0234 (4)	0.5097 (2)	0.0192 (9)
C8	0.8613 (6)	0.1634 (4)	0.4126 (3)	0.0236 (10)
C9	0.9133 (6)	0.2074 (5)	0.3309 (3)	0.0304 (12)
H9A	0.9629	0.1393	0.3109	0.037*
H9B	1.0056	0.2669	0.3274	0.037*
C10	0.7613 (6)	0.2650 (4)	0.2812 (3)	0.0229 (10)
C11	0.6621 (7)	0.3127 (5)	0.1547 (3)	0.0333 (12)
H11A	0.5579	0.2640	0.1625	0.050*
H11B	0.7086	0.3177	0.1034	0.050*
H11C	0.6319	0.3933	0.1621	0.050*
C12	0.6516 (7)	−0.1891 (5)	0.5159 (3)	0.0331 (12)
H12A	0.5628	−0.1639	0.4781	0.050*
H12B	0.6079	−0.2550	0.5550	0.050*
H12C	0.7571	−0.2158	0.4920	0.050*
C13	0.7001 (7)	0.4299 (5)	0.4797 (4)	0.0403 (14)
H13A	0.6444	0.3883	0.5267	0.060*
H13B	0.6317	0.4198	0.4371	0.060*
H13C	0.7069	0.5151	0.4798	0.060*
I2	1.27204 (4)	0.47039 (3)	0.246411 (19)	0.02932 (10)
S2	0.68848 (15)	0.62050 (11)	−0.02104 (6)	0.0208 (2)
O5	0.5483 (4)	0.7323 (3)	0.16778 (17)	0.0228 (7)
O6	0.2057 (4)	0.9129 (3)	−0.0229 (2)	0.0348 (9)
O7	0.5006 (4)	0.8964 (3)	−0.04426 (19)	0.0307 (8)
O8	0.7522 (4)	0.4897 (3)	−0.01091 (18)	0.0288 (8)
C14	0.6717 (6)	0.6561 (4)	0.0710 (2)	0.0192 (9)
C15	0.7950 (6)	0.6310 (4)	0.1331 (2)	0.0201 (9)
C16	0.9597 (6)	0.5710 (4)	0.1474 (3)	0.0226 (10)
H16	1.0203	0.5374	0.1103	0.027*
C17	1.0283 (6)	0.5640 (4)	0.2189 (3)	0.0241 (10)
C18	0.9410 (7)	0.6153 (4)	0.2756 (3)	0.0287 (11)
H18	0.9940	0.6092	0.3227	0.034*
C19	0.7787 (7)	0.6744 (5)	0.2632 (3)	0.0291 (11)
C20	0.7105 (6)	0.6795 (4)	0.1915 (3)	0.0221 (10)
C21	0.5275 (6)	0.7141 (4)	0.0946 (2)	0.0189 (9)
C22	0.3549 (6)	0.7575 (4)	0.0601 (3)	0.0232 (10)
H22A	0.2778	0.7819	0.0991	0.028*
H22B	0.3000	0.6902	0.0442	0.028*
C23	0.3682 (6)	0.8633 (4)	−0.0081 (3)	0.0215 (10)
C24	0.1942 (8)	1.0119 (5)	−0.0898 (3)	0.0457 (15)
H24A	0.2691	1.0767	−0.0837	0.069*
H24B	0.0737	1.0418	−0.0953	0.069*
H24C	0.2322	0.9828	−0.1347	0.069*
C25	0.6774 (8)	0.7295 (6)	0.3224 (3)	0.0482 (16)
H25A	0.7436	0.7163	0.3686	0.072*
H25B	0.5643	0.6917	0.3333	0.072*
H25C	0.6600	0.8155	0.3031	0.072*
C26	0.8772 (6)	0.7101 (5)	−0.0563 (3)	0.0284 (11)
H26A	0.9763	0.6818	−0.0243	0.043*
H26B	0.8507	0.7941	−0.0556	0.043*
H26C	0.9061	0.7024	−0.1079	0.043*

	U11	U22	U33	U12	U13	U23
I1	0.0579 (3)	0.0384 (2)	0.02000 (17)	0.01037 (17)	0.00379 (15)	−0.00193 (14)
S1	0.0221 (6)	0.0216 (6)	0.0315 (6)	−0.0007 (5)	−0.0032 (5)	−0.0038 (5)
O1	0.0225 (16)	0.0297 (18)	0.0195 (16)	0.0001 (14)	−0.0032 (13)	−0.0085 (14)
O2	0.0289 (18)	0.038 (2)	0.0172 (16)	0.0048 (15)	−0.0014 (14)	−0.0026 (14)
O3	0.0275 (19)	0.045 (2)	0.0254 (18)	0.0095 (16)	0.0018 (15)	−0.0014 (16)
O4	0.040 (2)	0.030 (2)	0.0317 (19)	−0.0043 (16)	−0.0048 (16)	−0.0033 (16)
C1	0.019 (2)	0.020 (2)	0.024 (2)	−0.0017 (18)	−0.0020 (18)	−0.0055 (19)
C2	0.016 (2)	0.017 (2)	0.024 (2)	0.0020 (17)	−0.0005 (17)	−0.0028 (18)
C3	0.024 (2)	0.021 (2)	0.021 (2)	0.0042 (18)	−0.0073 (18)	−0.0058 (18)
C4	0.020 (2)	0.029 (3)	0.020 (2)	0.0078 (19)	−0.0036 (18)	−0.0077 (19)
C5	0.022 (2)	0.018 (2)	0.032 (3)	0.0036 (18)	0.0000 (19)	−0.0002 (19)
C6	0.018 (2)	0.023 (2)	0.038 (3)	0.0060 (19)	−0.005 (2)	−0.009 (2)
C7	0.014 (2)	0.028 (2)	0.016 (2)	0.0004 (18)	−0.0050 (16)	−0.0048 (18)
C8	0.016 (2)	0.025 (2)	0.028 (2)	0.0031 (18)	−0.0052 (18)	−0.001 (2)
C9	0.021 (2)	0.048 (3)	0.020 (2)	0.005 (2)	0.0014 (19)	−0.002 (2)
C10	0.018 (2)	0.027 (3)	0.021 (2)	−0.0007 (19)	−0.0011 (18)	0.0006 (19)
C11	0.032 (3)	0.044 (3)	0.021 (2)	0.001 (2)	−0.005 (2)	−0.002 (2)
C12	0.026 (3)	0.028 (3)	0.048 (3)	0.001 (2)	−0.004 (2)	−0.015 (2)
C13	0.022 (3)	0.023 (3)	0.075 (4)	0.002 (2)	−0.007 (3)	−0.010 (3)
I2	0.02201 (16)	0.03174 (19)	0.03059 (18)	0.00357 (13)	−0.00415 (13)	0.00141 (14)
S2	0.0241 (6)	0.0247 (6)	0.0145 (5)	0.0012 (5)	−0.0013 (4)	−0.0061 (4)
O5	0.0260 (17)	0.0245 (17)	0.0187 (16)	0.0080 (13)	−0.0023 (13)	−0.0074 (13)
O6	0.0237 (18)	0.032 (2)	0.043 (2)	0.0059 (15)	−0.0063 (16)	0.0050 (16)
O7	0.0295 (19)	0.033 (2)	0.0262 (18)	0.0012 (15)	0.0048 (15)	0.0008 (15)
O8	0.037 (2)	0.0257 (18)	0.0240 (17)	0.0027 (15)	0.0050 (15)	−0.0080 (14)
C14	0.022 (2)	0.020 (2)	0.015 (2)	−0.0008 (18)	0.0016 (17)	−0.0042 (17)
C15	0.026 (2)	0.019 (2)	0.016 (2)	−0.0026 (18)	0.0017 (18)	−0.0044 (17)
C16	0.024 (2)	0.023 (2)	0.020 (2)	0.0008 (19)	0.0015 (18)	−0.0059 (19)
C17	0.022 (2)	0.020 (2)	0.027 (2)	0.0006 (19)	−0.0035 (19)	0.0011 (19)
C18	0.036 (3)	0.030 (3)	0.020 (2)	0.004 (2)	−0.011 (2)	−0.005 (2)
C19	0.041 (3)	0.031 (3)	0.016 (2)	0.010 (2)	−0.006 (2)	−0.009 (2)
C20	0.027 (2)	0.020 (2)	0.018 (2)	0.0035 (19)	−0.0024 (18)	−0.0028 (18)
C21	0.024 (2)	0.019 (2)	0.014 (2)	−0.0021 (18)	−0.0015 (17)	−0.0018 (17)
C22	0.022 (2)	0.030 (3)	0.017 (2)	−0.0006 (19)	0.0015 (18)	−0.0037 (19)
C23	0.027 (2)	0.015 (2)	0.026 (2)	0.0066 (19)	0.001 (2)	−0.0125 (19)
C24	0.037 (3)	0.038 (3)	0.053 (4)	0.011 (3)	−0.011 (3)	0.011 (3)
C25	0.057 (4)	0.066 (4)	0.027 (3)	0.029 (3)	−0.011 (3)	−0.023 (3)
C26	0.031 (3)	0.032 (3)	0.021 (2)	−0.004 (2)	0.008 (2)	−0.002 (2)

I1—C4	2.103 (4)	I2—C17	2.108 (4)
I1—O7i	3.300 (3)	I2—O3iii	3.264 (3)
S1—O4	1.482 (4)	S2—O8	1.505 (3)
S1—C1	1.773 (5)	S2—C14	1.771 (4)
S1—C13	1.800 (5)	S2—C26	1.786 (5)
S1—O4ii	3.025 (4)	O5—C21	1.379 (5)
O1—C7	1.375 (5)	O5—C20	1.382 (5)
O1—C8	1.378 (6)	O6—C23	1.341 (5)
O2—C10	1.326 (6)	O6—C24	1.451 (6)
O2—C11	1.442 (6)	O7—C23	1.196 (5)
O3—C10	1.198 (5)	C14—C21	1.351 (6)
C1—C8	1.349 (6)	C14—C15	1.446 (6)
C1—C2	1.435 (6)	C15—C20	1.400 (6)
C2—C3	1.397 (6)	C15—C16	1.400 (6)
C2—C7	1.403 (6)	C16—C17	1.379 (6)
C3—C4	1.378 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.403 (7)
C4—C5	1.395 (7)	C18—C19	1.376 (7)
C5—C6	1.397 (7)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.385 (6)
C6—C7	1.371 (7)	C19—C25	1.509 (7)
C6—C12	1.507 (7)	C21—C22	1.482 (6)
C8—C9	1.481 (6)	C22—C23	1.511 (6)
C9—C10	1.516 (6)	C22—H22A	0.9700
C9—H9A	0.9700	C22—H22B	0.9700
C9—H9B	0.9700	C24—H24A	0.9600
C11—H11A	0.9600	C24—H24B	0.9600
C11—H11B	0.9600	C24—H24C	0.9600
C11—H11C	0.9600	C25—H25A	0.9600
C12—H12A	0.9600	C25—H25B	0.9600
C12—H12B	0.9600	C25—H25C	0.9600
C12—H12C	0.9600	C26—H26A	0.9600
C13—H13A	0.9600	C26—H26B	0.9600
C13—H13B	0.9600	C26—H26C	0.9600
C13—H13C	0.9600
I1···O7i	3.300 (3)	I2···O3iii	3.264 (3)
C4—I1—O7i	160.08 (15)	H13B—C13—H13C	109.5
O4—S1—C1	105.7 (2)	C17—I2—O3iii	174.78 (14)
O4—S1—C13	106.0 (3)	O8—S2—C14	107.7 (2)
C1—S1—C13	97.4 (2)	O8—S2—C26	105.5 (2)
O4—S1—O4ii	78.94 (17)	C14—S2—C26	97.6 (2)
C1—S1—O4ii	174.59 (17)	C21—O5—C20	106.4 (3)
C13—S1—O4ii	78.48 (18)	C23—O6—C24	115.7 (4)
C7—O1—C8	106.4 (3)	C21—C14—C15	107.9 (4)
C10—O2—C11	116.0 (4)	C21—C14—S2	122.2 (3)
C8—C1—C2	108.3 (4)	C15—C14—S2	130.0 (3)
C8—C1—S1	123.4 (4)	C20—C15—C16	118.7 (4)
C2—C1—S1	128.3 (3)	C20—C15—C14	104.4 (4)
C3—C2—C7	119.1 (4)	C16—C15—C14	136.8 (4)
C3—C2—C1	136.7 (4)	C17—C16—C15	117.0 (4)
C7—C2—C1	104.2 (4)	C17—C16—H16	121.5
C4—C3—C2	116.8 (4)	C15—C16—H16	121.5
C4—C3—H3	121.6	C16—C17—C18	122.7 (4)
C2—C3—H3	121.6	C16—C17—I2	119.5 (3)
C3—C4—C5	123.2 (4)	C18—C17—I2	117.8 (3)
C3—C4—I1	119.8 (3)	C19—C18—C17	121.4 (4)
C5—C4—I1	117.1 (3)	C19—C18—H18	119.3
C4—C5—C6	120.7 (4)	C17—C18—H18	119.3
C4—C5—H5	119.6	C18—C19—C20	115.2 (4)
C6—C5—H5	119.6	C18—C19—C25	123.8 (4)
C7—C6—C5	115.5 (4)	C20—C19—C25	121.0 (5)
C7—C6—C12	122.6 (5)	O5—C20—C19	124.6 (4)
C5—C6—C12	121.8 (5)	O5—C20—C15	110.5 (4)
C6—C7—O1	124.8 (4)	C19—C20—C15	124.9 (4)
C6—C7—C2	124.6 (4)	C14—C21—O5	110.8 (4)
O1—C7—C2	110.6 (4)	C14—C21—C22	134.1 (4)
C1—C8—O1	110.5 (4)	O5—C21—C22	115.1 (4)
C1—C8—C9	133.7 (5)	C21—C22—C23	114.2 (4)
O1—C8—C9	115.8 (4)	C21—C22—H22A	108.7
C8—C9—C10	113.7 (4)	C23—C22—H22A	108.7
C8—C9—H9A	108.8	C21—C22—H22B	108.7
C10—C9—H9A	108.8	C23—C22—H22B	108.7
C8—C9—H9B	108.8	H22A—C22—H22B	107.6
C10—C9—H9B	108.8	O7—C23—O6	125.1 (4)
H9A—C9—H9B	107.7	O7—C23—C22	126.0 (4)
O3—C10—O2	124.9 (4)	O6—C23—C22	108.8 (4)
O3—C10—C9	124.9 (4)	O6—C24—H24A	109.5
O2—C10—C9	110.2 (4)	O6—C24—H24B	109.5
O2—C11—H11A	109.5	H24A—C24—H24B	109.5
O2—C11—H11B	109.5	O6—C24—H24C	109.5
H11A—C11—H11B	109.5	H24A—C24—H24C	109.5
O2—C11—H11C	109.5	H24B—C24—H24C	109.5
H11A—C11—H11C	109.5	C19—C25—H25A	109.5
H11B—C11—H11C	109.5	C19—C25—H25B	109.5
C6—C12—H12A	109.5	H25A—C25—H25B	109.5
C6—C12—H12B	109.5	C19—C25—H25C	109.5
H12A—C12—H12B	109.5	H25A—C25—H25C	109.5
C6—C12—H12C	109.5	H25B—C25—H25C	109.5
H12A—C12—H12C	109.5	S2—C26—H26A	109.5
H12B—C12—H12C	109.5	S2—C26—H26B	109.5
S1—C13—H13A	109.5	H26A—C26—H26B	109.5
S1—C13—H13B	109.5	S2—C26—H26C	109.5
H13A—C13—H13B	109.5	H26A—C26—H26C	109.5
S1—C13—H13C	109.5	H26B—C26—H26C	109.5
H13A—C13—H13C	109.5
O4—S1—C1—C8	−146.0 (4)	C8—C9—C10—O2	−155.0 (4)
C13—S1—C1—C8	105.1 (4)	O8—S2—C14—C21	−133.1 (4)
O4—S1—C1—C2	35.0 (5)	C26—S2—C14—C21	117.9 (4)
C13—S1—C1—C2	−74.0 (5)	O8—S2—C14—C15	45.9 (5)
C8—C1—C2—C3	176.9 (5)	C26—S2—C14—C15	−63.1 (5)
S1—C1—C2—C3	−4.0 (8)	C21—C14—C15—C20	−0.5 (5)
C8—C1—C2—C7	−2.0 (5)	S2—C14—C15—C20	−179.6 (4)
S1—C1—C2—C7	177.2 (3)	C21—C14—C15—C16	176.6 (5)
C7—C2—C3—C4	−2.1 (6)	S2—C14—C15—C16	−2.5 (8)
C1—C2—C3—C4	179.2 (5)	C20—C15—C16—C17	−0.1 (6)
C2—C3—C4—C5	0.1 (7)	C14—C15—C16—C17	−176.9 (5)
C2—C3—C4—I1	179.4 (3)	C15—C16—C17—C18	−0.9 (7)
O7i—I1—C4—C3	150.8 (3)	C15—C16—C17—I2	178.1 (3)
O7i—I1—C4—C5	−29.9 (6)	C16—C17—C18—C19	1.1 (8)
C3—C4—C5—C6	1.0 (7)	I2—C17—C18—C19	−177.9 (4)
I1—C4—C5—C6	−178.2 (3)	C17—C18—C19—C20	−0.3 (7)
C4—C5—C6—C7	−0.1 (6)	C17—C18—C19—C25	179.0 (5)
C4—C5—C6—C12	179.5 (4)	C21—O5—C20—C19	−177.8 (5)
C5—C6—C7—O1	179.3 (4)	C21—O5—C20—C15	1.7 (5)
C12—C6—C7—O1	−0.3 (7)	C18—C19—C20—O5	178.6 (4)
C5—C6—C7—C2	−2.0 (7)	C25—C19—C20—O5	−0.6 (8)
C12—C6—C7—C2	178.4 (4)	C18—C19—C20—C15	−0.7 (8)
C8—O1—C7—C6	179.0 (4)	C25—C19—C20—C15	−180.0 (5)
C8—O1—C7—C2	0.1 (5)	C16—C15—C20—O5	−178.5 (4)
C3—C2—C7—C6	3.2 (7)	C14—C15—C20—O5	−0.7 (5)
C1—C2—C7—C6	−177.7 (4)	C16—C15—C20—C19	0.9 (7)
C3—C2—C7—O1	−178.0 (4)	C14—C15—C20—C19	178.7 (5)
C1—C2—C7—O1	1.1 (5)	C15—C14—C21—O5	1.6 (5)
C2—C1—C8—O1	2.2 (5)	S2—C14—C21—O5	−179.2 (3)
S1—C1—C8—O1	−177.0 (3)	C15—C14—C21—C22	−176.3 (5)
C2—C1—C8—C9	−178.5 (5)	S2—C14—C21—C22	2.9 (7)
S1—C1—C8—C9	2.3 (8)	C20—O5—C21—C14	−2.0 (5)
C7—O1—C8—C1	−1.4 (5)	C20—O5—C21—C22	176.3 (4)
C7—O1—C8—C9	179.1 (4)	C14—C21—C22—C23	−68.7 (7)
C1—C8—C9—C10	−92.0 (6)	O5—C21—C22—C23	113.6 (4)
O1—C8—C9—C10	87.3 (5)	C24—O6—C23—O7	1.9 (7)
C11—O2—C10—O3	0.4 (7)	C24—O6—C23—C22	−176.7 (4)
C11—O2—C10—C9	−177.9 (4)	C21—C22—C23—O7	15.9 (7)
C8—C9—C10—O3	26.6 (7)	C21—C22—C23—O6	−165.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3iv	0.93	2.59	3.430 (6)	150
C11—H11B···O8	0.96	2.51	3.254 (6)	134
C12—H12C···O4v	0.96	2.58	3.489 (6)	158
C16—H16···O8vi	0.93	2.48	3.373 (6)	160
C18—H18···O4ii	0.93	2.44	3.297 (6)	153
C22—H22B···O8vii	0.97	2.27	3.215 (6)	164
C12—H12A···Cg1iv	0.96	2.85	3.734 (7)	153
C24—H24A···Cg3viii	0.96	2.73	3.574 (7)	147

Table 1

Selected interatomic distances (Å)

I1⋯O7i	3.300 (3)
I2⋯O3ii	3.264 (3)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3iii	0.93	2.59	3.430 (6)	150
C11—H11B⋯O8	0.96	2.51	3.254 (6)	134
C12—H12C⋯O4iv	0.96	2.58	3.489 (6)	158
C16—H16⋯O8v	0.93	2.48	3.373 (6)	160
C18—H18⋯O4vi	0.93	2.44	3.297 (6)	153
C22—H22B⋯O8vii	0.97	2.27	3.215 (6)	164
C12—H12A⋯Cg1iii	0.96	2.85	3.734 (7)	153
C24—H24A⋯Cg3viii	0.96	2.73	3.574 (7)	147

Symmetry codes: (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) . Cg1 and Cg3 are the centroids of the C2–C7 benzene ring and the C14/C15/C20/O5/C21 furan ring, respectively.