5-(4-Fluoro-phen-yl)-2-(4-methyl-phen-yl)-3-methyl-sulfanyl-1-benzo-furan.

The asymmetric unit of the title compound, C22H17FOS, contains two independent mol-ecules (A and B). The dihedral angles between the benzo-furan ring systems [r.m.s. deviations of 0.026 (1), 0.004 (1) and 0.003 (1) Å, respectively, for mol-ecule A, and 0.002 (1), 0.004 (1) and 0.005 (1) Å for B] and the pendant 4-fluoro-phenyl and 4-methyl-phenyl rings are 39.48 (4) and 30.86 (5)°, respectively, for mol-ecule A, and 33.34 (6) and 20.99 (8)° for B. In the crystal, mol-ecules are linked by weak C-H⋯F and C-H⋯π inter-actions, resulting in a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C22H17FOS

M = 348.42

Monoclinic,

a = 17.897 (6) Å

b = 10.753 (3) Å

c = 17.775 (5) Å

β = 98.541 (18)°

V = 3382.8 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.43 × 0.36 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.681, T max = 0.746

55108 measured reflections

7388 independent reflections

5723 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.03

7388 reflections

454 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.37 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/S1600536814002402/bx2454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002402/bx2454Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002402/bx2454Isup3.cml

CCDC reference:

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

C22H17FOS	F(000) = 1456
Mr = 348.42	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Melting point = 425–426 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.897 (6) Å	Cell parameters from 9590 reflections
b = 10.753 (3) Å	θ = 2.2–26.3°
c = 17.775 (5) Å	µ = 0.21 mm−1
β = 98.541 (18)°	T = 173 K
V = 3382.8 (18) Å3	Block, colourless
Z = 8	0.43 × 0.36 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	7388 independent reflections
Radiation source: rotating anode	5723 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.051
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.2°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.681, Tmax = 0.746	l = −22→22
55108 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2 + 1.2362P] where P = (Fo2 + 2Fc2)/3
7388 reflections	(Δ/σ)max = 0.001
454 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.37 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	0.37299 (2)	0.21067 (4)	0.29473 (2)	0.02650 (11)
F1	0.06413 (7)	0.84290 (10)	0.44228 (7)	0.0486 (3)
O1	0.23646 (6)	−0.00311 (10)	0.39568 (7)	0.0263 (3)
C1	0.30874 (9)	0.14077 (15)	0.34763 (9)	0.0237 (3)
C2	0.25213 (9)	0.20428 (15)	0.38362 (9)	0.0241 (3)
C3	0.23108 (9)	0.32782 (15)	0.39093 (9)	0.0252 (4)
H3	0.2594	0.3931	0.3728	0.030*
C4	0.16752 (9)	0.35447 (15)	0.42539 (9)	0.0262 (4)
C5	0.12703 (10)	0.25676 (16)	0.45380 (10)	0.0290 (4)
H5	0.0847	0.2763	0.4781	0.035*
C6	0.14701 (10)	0.13436 (16)	0.44740 (10)	0.0288 (4)
H6	0.1196	0.0688	0.4664	0.035*
C7	0.20949 (9)	0.11165 (15)	0.41162 (9)	0.0253 (4)
C8	0.29684 (9)	0.01726 (15)	0.35648 (9)	0.0241 (3)
C9	0.14098 (9)	0.48411 (15)	0.43128 (9)	0.0261 (4)
C10	0.06343 (10)	0.51114 (17)	0.42028 (10)	0.0316 (4)
H10	0.0281	0.4451	0.4101	0.038*
C11	0.03721 (10)	0.63092 (18)	0.42381 (10)	0.0352 (4)
H11	−0.0154	0.6485	0.4158	0.042*
C12	0.08954 (11)	0.72404 (16)	0.43927 (10)	0.0336 (4)
C13	0.16654 (11)	0.70297 (17)	0.45160 (10)	0.0327 (4)
H13	0.2012	0.7697	0.4629	0.039*
C14	0.19175 (10)	0.58206 (16)	0.44707 (10)	0.0293 (4)
H14	0.2445	0.5656	0.4548	0.035*
C15	0.33306 (9)	−0.09598 (15)	0.33398 (9)	0.0246 (3)
C16	0.41086 (9)	−0.10156 (16)	0.32995 (9)	0.0274 (4)
H16	0.4412	−0.0293	0.3405	0.033*
C17	0.44362 (10)	−0.21136 (16)	0.31081 (9)	0.0286 (4)
H17	0.4963	−0.2135	0.3084	0.034*
C18	0.40082 (10)	−0.31842 (15)	0.29508 (9)	0.0277 (4)
C19	0.32341 (10)	−0.31272 (15)	0.30001 (9)	0.0277 (4)
H19	0.2934	−0.3854	0.2901	0.033*
C20	0.28997 (10)	−0.20375 (15)	0.31890 (9)	0.0265 (4)
H20	0.2374	−0.2021	0.3217	0.032*
C21	0.43623 (11)	−0.43679 (17)	0.27212 (11)	0.0371 (4)
H21A	0.4764	−0.4628	0.3127	0.045*
H21B	0.4577	−0.4226	0.2252	0.045*
H21C	0.3977	−0.5020	0.2635	0.045*
C22	0.45009 (10)	0.24833 (18)	0.36934 (11)	0.0375 (4)
H22A	0.4314	0.3014	0.4073	0.056*
H22B	0.4896	0.2925	0.3474	0.056*
H22C	0.4710	0.1715	0.3936	0.056*
S2	0.12675 (3)	0.49163 (4)	0.20081 (3)	0.03560 (13)
F2	0.41994 (6)	1.12966 (9)	0.04363 (7)	0.0422 (3)
O2	0.27237 (6)	0.27471 (10)	0.11261 (6)	0.0262 (3)
C23	0.19837 (9)	0.41799 (16)	0.15898 (9)	0.0270 (4)
C24	0.25573 (9)	0.48150 (15)	0.12453 (9)	0.0256 (4)
C25	0.27344 (9)	0.60571 (15)	0.11360 (9)	0.0253 (3)
H25	0.2442	0.6701	0.1315	0.030*
C26	0.33444 (9)	0.63484 (15)	0.07614 (9)	0.0239 (3)
C27	0.37678 (9)	0.53799 (16)	0.04921 (10)	0.0267 (4)
H27	0.4180	0.5587	0.0235	0.032*
C28	0.36017 (9)	0.41427 (15)	0.05910 (10)	0.0274 (4)
H28	0.3889	0.3495	0.0410	0.033*
C29	0.29921 (9)	0.38949 (15)	0.09688 (9)	0.0249 (4)
C30	0.21047 (9)	0.29419 (15)	0.15035 (9)	0.0252 (3)
C31	0.35593 (9)	0.76637 (15)	0.06618 (9)	0.0232 (3)
C32	0.34603 (9)	0.85462 (15)	0.12153 (9)	0.0259 (4)
H32	0.3243	0.8300	0.1649	0.031*
C33	0.36720 (9)	0.97693 (15)	0.11432 (10)	0.0277 (4)
H33	0.3607	1.0366	0.1522	0.033*
C34	0.39803 (10)	1.01017 (15)	0.05080 (10)	0.0291 (4)
C35	0.40837 (9)	0.92699 (16)	−0.00564 (10)	0.0282 (4)
H35	0.4294	0.9529	−0.0491	0.034*
C36	0.38730 (9)	0.80506 (15)	0.00268 (9)	0.0254 (3)
H36	0.3942	0.7462	−0.0355	0.030*
C37	0.17303 (9)	0.18137 (15)	0.17111 (9)	0.0251 (4)
C38	0.12785 (10)	0.17959 (17)	0.22887 (10)	0.0312 (4)
H38	0.1201	0.2542	0.2553	0.037*
C39	0.09441 (10)	0.07072 (17)	0.24784 (10)	0.0335 (4)
H39	0.0635	0.0718	0.2869	0.040*
C40	0.10489 (10)	−0.04023 (17)	0.21115 (10)	0.0308 (4)
C41	0.14927 (10)	−0.03773 (17)	0.15302 (11)	0.0336 (4)
H41	0.1565	−0.1124	0.1265	0.040*
C42	0.18297 (10)	0.07025 (16)	0.13297 (10)	0.0291 (4)
H42	0.2130	0.0691	0.0932	0.035*
C43	0.06869 (12)	−0.15786 (18)	0.23410 (12)	0.0441 (5)
H43A	0.0526	−0.1461	0.2840	0.066*
H43B	0.1052	−0.2262	0.2370	0.066*
H43C	0.0247	−0.1779	0.1963	0.066*
C44	0.07083 (11)	0.5533 (2)	0.11587 (12)	0.0441 (5)
H44A	0.1030	0.6040	0.0879	0.066*
H44B	0.0300	0.6048	0.1301	0.066*
H44C	0.0492	0.4845	0.0836	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0272 (2)	0.0265 (2)	0.0265 (2)	−0.00032 (16)	0.00621 (17)	0.00148 (16)
F1	0.0554 (7)	0.0297 (6)	0.0587 (7)	0.0154 (5)	0.0019 (6)	−0.0058 (5)
O1	0.0268 (6)	0.0222 (6)	0.0312 (6)	0.0011 (5)	0.0085 (5)	0.0004 (5)
C1	0.0223 (8)	0.0247 (8)	0.0241 (8)	0.0011 (6)	0.0030 (7)	0.0004 (6)
C2	0.0218 (8)	0.0268 (8)	0.0231 (8)	0.0006 (6)	0.0015 (7)	0.0004 (6)
C3	0.0233 (8)	0.0236 (8)	0.0284 (8)	−0.0006 (6)	0.0030 (7)	−0.0016 (7)
C4	0.0235 (8)	0.0273 (9)	0.0270 (8)	0.0012 (7)	0.0007 (7)	−0.0032 (7)
C5	0.0250 (9)	0.0325 (9)	0.0304 (9)	0.0001 (7)	0.0072 (7)	−0.0045 (7)
C6	0.0288 (9)	0.0295 (9)	0.0294 (9)	−0.0024 (7)	0.0083 (7)	−0.0007 (7)
C7	0.0260 (9)	0.0239 (8)	0.0255 (8)	0.0020 (6)	0.0024 (7)	−0.0014 (6)
C8	0.0223 (8)	0.0262 (8)	0.0237 (8)	0.0010 (6)	0.0031 (7)	0.0008 (6)
C9	0.0259 (9)	0.0284 (9)	0.0241 (8)	0.0029 (7)	0.0039 (7)	−0.0034 (7)
C10	0.0257 (9)	0.0336 (10)	0.0347 (9)	0.0004 (7)	0.0012 (8)	−0.0065 (8)
C11	0.0263 (9)	0.0403 (11)	0.0377 (10)	0.0094 (8)	0.0010 (8)	−0.0056 (8)
C12	0.0430 (11)	0.0281 (9)	0.0290 (9)	0.0099 (8)	0.0032 (8)	−0.0026 (7)
C13	0.0367 (10)	0.0283 (9)	0.0332 (9)	−0.0023 (8)	0.0051 (8)	−0.0024 (7)
C14	0.0259 (9)	0.0297 (9)	0.0322 (9)	0.0016 (7)	0.0044 (7)	−0.0006 (7)
C15	0.0276 (9)	0.0237 (8)	0.0226 (8)	0.0024 (7)	0.0038 (7)	0.0025 (6)
C16	0.0284 (9)	0.0252 (8)	0.0288 (9)	−0.0007 (7)	0.0045 (7)	0.0014 (7)
C17	0.0271 (9)	0.0305 (9)	0.0286 (9)	0.0037 (7)	0.0056 (7)	0.0025 (7)
C18	0.0352 (9)	0.0248 (8)	0.0233 (8)	0.0058 (7)	0.0050 (7)	0.0031 (7)
C19	0.0350 (10)	0.0237 (8)	0.0240 (8)	−0.0019 (7)	0.0027 (7)	0.0010 (7)
C20	0.0256 (8)	0.0274 (9)	0.0263 (8)	−0.0003 (7)	0.0033 (7)	0.0011 (7)
C21	0.0443 (11)	0.0298 (10)	0.0382 (10)	0.0089 (8)	0.0093 (9)	−0.0009 (8)
C22	0.0319 (10)	0.0365 (10)	0.0427 (11)	−0.0060 (8)	0.0009 (8)	0.0003 (8)
S2	0.0374 (3)	0.0324 (3)	0.0401 (3)	0.00336 (19)	0.0163 (2)	−0.00116 (19)
F2	0.0504 (7)	0.0216 (5)	0.0580 (7)	−0.0052 (5)	0.0193 (6)	−0.0003 (5)
O2	0.0250 (6)	0.0221 (6)	0.0318 (6)	−0.0013 (4)	0.0056 (5)	−0.0007 (5)
C23	0.0267 (9)	0.0274 (9)	0.0271 (8)	−0.0001 (7)	0.0048 (7)	−0.0018 (7)
C24	0.0245 (8)	0.0268 (9)	0.0251 (8)	0.0006 (7)	0.0023 (7)	−0.0012 (7)
C25	0.0252 (8)	0.0237 (8)	0.0269 (8)	0.0012 (6)	0.0036 (7)	−0.0022 (7)
C26	0.0240 (8)	0.0233 (8)	0.0230 (8)	−0.0007 (6)	−0.0007 (7)	−0.0014 (6)
C27	0.0239 (8)	0.0271 (9)	0.0295 (9)	−0.0015 (7)	0.0050 (7)	−0.0019 (7)
C28	0.0257 (9)	0.0247 (9)	0.0321 (9)	0.0026 (7)	0.0054 (7)	−0.0035 (7)
C29	0.0250 (8)	0.0218 (8)	0.0270 (8)	−0.0013 (6)	0.0010 (7)	−0.0010 (6)
C30	0.0215 (8)	0.0294 (9)	0.0243 (8)	−0.0003 (7)	0.0019 (7)	−0.0022 (7)
C31	0.0191 (8)	0.0232 (8)	0.0259 (8)	0.0007 (6)	−0.0010 (6)	−0.0001 (6)
C32	0.0257 (9)	0.0262 (9)	0.0259 (8)	0.0012 (7)	0.0040 (7)	0.0002 (7)
C33	0.0282 (9)	0.0243 (8)	0.0303 (9)	0.0019 (7)	0.0038 (7)	−0.0054 (7)
C34	0.0269 (9)	0.0213 (8)	0.0387 (10)	−0.0021 (7)	0.0033 (8)	0.0021 (7)
C35	0.0261 (9)	0.0307 (9)	0.0283 (9)	−0.0012 (7)	0.0059 (7)	0.0024 (7)
C36	0.0240 (8)	0.0269 (8)	0.0250 (8)	0.0012 (7)	0.0026 (7)	−0.0027 (7)
C37	0.0226 (8)	0.0267 (8)	0.0248 (8)	−0.0005 (6)	−0.0005 (7)	0.0014 (7)
C38	0.0336 (10)	0.0313 (9)	0.0282 (9)	−0.0034 (7)	0.0028 (8)	−0.0047 (7)
C39	0.0337 (10)	0.0392 (10)	0.0286 (9)	−0.0036 (8)	0.0075 (8)	0.0011 (8)
C40	0.0300 (9)	0.0298 (9)	0.0316 (9)	−0.0020 (7)	0.0005 (7)	0.0068 (7)
C41	0.0346 (10)	0.0250 (9)	0.0413 (10)	0.0013 (7)	0.0063 (8)	−0.0005 (8)
C42	0.0282 (9)	0.0280 (9)	0.0320 (9)	0.0012 (7)	0.0076 (7)	0.0010 (7)
C43	0.0476 (12)	0.0358 (11)	0.0505 (12)	−0.0039 (9)	0.0120 (10)	0.0113 (9)
C44	0.0317 (10)	0.0470 (12)	0.0538 (13)	0.0058 (9)	0.0065 (9)	−0.0034 (10)

S1—C1	1.7586 (17)	S2—C23	1.7623 (18)
S1—C22	1.8119 (19)	S2—C44	1.809 (2)
F1—C12	1.360 (2)	F2—C34	1.3550 (19)
O1—C7	1.3699 (19)	O2—C29	1.3683 (19)
O1—C8	1.388 (2)	O2—C30	1.393 (2)
C1—C8	1.358 (2)	C23—C30	1.361 (2)
C1—C2	1.447 (2)	C23—C24	1.443 (2)
C2—C7	1.391 (2)	C24—C29	1.393 (2)
C2—C3	1.392 (2)	C24—C25	1.393 (2)
C3—C4	1.399 (2)	C25—C26	1.396 (2)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.412 (2)	C26—C27	1.413 (2)
C4—C9	1.481 (2)	C26—C31	1.483 (2)
C5—C6	1.373 (2)	C27—C28	1.380 (2)
C5—H5	0.9500	C27—H27	0.9500
C6—C7	1.388 (2)	C28—C29	1.389 (2)
C6—H6	0.9500	C28—H28	0.9500
C8—C15	1.463 (2)	C30—C37	1.460 (2)
C9—C14	1.392 (2)	C31—C36	1.397 (2)
C9—C10	1.403 (2)	C31—C32	1.397 (2)
C10—C11	1.375 (3)	C32—C33	1.380 (2)
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.371 (3)	C33—C34	1.375 (3)
C11—H11	0.9500	C33—H33	0.9500
C12—C13	1.382 (3)	C34—C35	1.377 (2)
C13—C14	1.382 (2)	C35—C36	1.378 (2)
C13—H13	0.9500	C35—H35	0.9500
C14—H14	0.9500	C36—H36	0.9500
C15—C20	1.396 (2)	C37—C42	1.398 (2)
C15—C16	1.406 (2)	C37—C38	1.398 (2)
C16—C17	1.383 (2)	C38—C39	1.379 (3)
C16—H16	0.9500	C38—H38	0.9500
C17—C18	1.388 (2)	C39—C40	1.386 (3)
C17—H17	0.9500	C39—H39	0.9500
C18—C19	1.402 (3)	C40—C41	1.394 (3)
C18—C21	1.505 (2)	C40—C43	1.505 (3)
C19—C20	1.380 (2)	C41—C42	1.379 (2)
C19—H19	0.9500	C41—H41	0.9500
C20—H20	0.9500	C42—H42	0.9500
C21—H21A	0.9800	C43—H43A	0.9800
C21—H21B	0.9800	C43—H43B	0.9800
C21—H21C	0.9800	C43—H43C	0.9800
C22—H22A	0.9800	C44—H44A	0.9800
C22—H22B	0.9800	C44—H44B	0.9800
C22—H22C	0.9800	C44—H44C	0.9800
C1—S1—C22	101.05 (9)	C23—S2—C44	99.18 (9)
C7—O1—C8	106.64 (12)	C29—O2—C30	106.93 (12)
C8—C1—C2	106.15 (14)	C30—C23—C24	106.25 (15)
C8—C1—S1	127.32 (13)	C30—C23—S2	128.68 (14)
C2—C1—S1	126.22 (12)	C24—C23—S2	125.05 (13)
C7—C2—C3	118.64 (15)	C29—C24—C25	118.77 (16)
C7—C2—C1	106.11 (14)	C29—C24—C23	106.47 (15)
C3—C2—C1	135.11 (16)	C25—C24—C23	134.74 (16)
C2—C3—C4	119.02 (16)	C24—C25—C26	119.46 (15)
C2—C3—H3	120.5	C24—C25—H25	120.3
C4—C3—H3	120.5	C26—C25—H25	120.3
C3—C4—C5	119.87 (15)	C25—C26—C27	119.54 (15)
C3—C4—C9	120.91 (15)	C25—C26—C31	120.39 (15)
C5—C4—C9	119.21 (15)	C27—C26—C31	120.05 (15)
C6—C5—C4	122.01 (16)	C28—C27—C26	122.06 (16)
C6—C5—H5	119.0	C28—C27—H27	119.0
C4—C5—H5	119.0	C26—C27—H27	119.0
C5—C6—C7	116.37 (16)	C27—C28—C29	116.49 (15)
C5—C6—H6	121.8	C27—C28—H28	121.8
C7—C6—H6	121.8	C29—C28—H28	121.8
O1—C7—C6	125.87 (15)	O2—C29—C28	126.63 (15)
O1—C7—C2	110.01 (14)	O2—C29—C24	109.70 (14)
C6—C7—C2	124.07 (16)	C28—C29—C24	123.67 (15)
C1—C8—O1	111.09 (14)	C23—C30—O2	110.64 (15)
C1—C8—C15	134.35 (16)	C23—C30—C37	134.24 (16)
O1—C8—C15	114.57 (14)	O2—C30—C37	115.11 (14)
C14—C9—C10	118.29 (16)	C36—C31—C32	118.37 (15)
C14—C9—C4	121.31 (15)	C36—C31—C26	121.54 (15)
C10—C9—C4	120.40 (15)	C32—C31—C26	120.09 (15)
C11—C10—C9	121.66 (17)	C33—C32—C31	121.11 (16)
C11—C10—H10	119.2	C33—C32—H32	119.4
C9—C10—H10	119.2	C31—C32—H32	119.4
C12—C11—C10	117.74 (17)	C34—C33—C32	118.24 (16)
C12—C11—H11	121.1	C34—C33—H33	120.9
C10—C11—H11	121.1	C32—C33—H33	120.9
F1—C12—C11	118.15 (17)	F2—C34—C33	118.73 (15)
F1—C12—C13	118.64 (17)	F2—C34—C35	118.38 (16)
C11—C12—C13	123.21 (17)	C33—C34—C35	122.89 (16)
C12—C13—C14	118.13 (17)	C34—C35—C36	118.11 (16)
C12—C13—H13	120.9	C34—C35—H35	120.9
C14—C13—H13	120.9	C36—C35—H35	120.9
C13—C14—C9	120.95 (16)	C35—C36—C31	121.29 (16)
C13—C14—H14	119.5	C35—C36—H36	119.4
C9—C14—H14	119.5	C31—C36—H36	119.4
C20—C15—C16	118.55 (15)	C42—C37—C38	118.26 (16)
C20—C15—C8	119.27 (15)	C42—C37—C30	119.43 (15)
C16—C15—C8	122.13 (15)	C38—C37—C30	122.30 (15)
C17—C16—C15	120.54 (16)	C39—C38—C37	120.69 (17)
C17—C16—H16	119.7	C39—C38—H38	119.7
C15—C16—H16	119.7	C37—C38—H38	119.7
C16—C17—C18	121.08 (16)	C38—C39—C40	121.44 (18)
C16—C17—H17	119.5	C38—C39—H39	119.3
C18—C17—H17	119.5	C40—C39—H39	119.3
C17—C18—C19	118.15 (15)	C39—C40—C41	117.66 (17)
C17—C18—C21	120.93 (17)	C39—C40—C43	120.14 (17)
C19—C18—C21	120.91 (16)	C41—C40—C43	122.20 (17)
C20—C19—C18	121.38 (16)	C42—C41—C40	121.80 (17)
C20—C19—H19	119.3	C42—C41—H41	119.1
C18—C19—H19	119.3	C40—C41—H41	119.1
C19—C20—C15	120.30 (16)	C41—C42—C37	120.14 (17)
C19—C20—H20	119.9	C41—C42—H42	119.9
C15—C20—H20	119.9	C37—C42—H42	119.9
C18—C21—H21A	109.5	C40—C43—H43A	109.5
C18—C21—H21B	109.5	C40—C43—H43B	109.5
H21A—C21—H21B	109.5	H43A—C43—H43B	109.5
C18—C21—H21C	109.5	C40—C43—H43C	109.5
H21A—C21—H21C	109.5	H43A—C43—H43C	109.5
H21B—C21—H21C	109.5	H43B—C43—H43C	109.5
S1—C22—H22A	109.5	S2—C44—H44A	109.5
S1—C22—H22B	109.5	S2—C44—H44B	109.5
H22A—C22—H22B	109.5	H44A—C44—H44B	109.5
S1—C22—H22C	109.5	S2—C44—H44C	109.5
H22A—C22—H22C	109.5	H44A—C44—H44C	109.5
H22B—C22—H22C	109.5	H44B—C44—H44C	109.5
C22—S1—C1—C8	−99.82 (16)	C44—S2—C23—C30	−108.34 (17)
C22—S1—C1—C2	87.45 (15)	C44—S2—C23—C24	69.81 (16)
C8—C1—C2—C7	−0.26 (17)	C30—C23—C24—C29	0.09 (18)
S1—C1—C2—C7	173.73 (12)	S2—C23—C24—C29	−178.40 (12)
C8—C1—C2—C3	−175.84 (18)	C30—C23—C24—C25	178.91 (18)
S1—C1—C2—C3	−1.8 (3)	S2—C23—C24—C25	0.4 (3)
C7—C2—C3—C4	−0.6 (2)	C29—C24—C25—C26	−0.7 (2)
C1—C2—C3—C4	174.53 (16)	C23—C24—C25—C26	−179.37 (17)
C2—C3—C4—C5	1.6 (2)	C24—C25—C26—C27	0.6 (2)
C2—C3—C4—C9	−177.22 (15)	C24—C25—C26—C31	−177.91 (14)
C3—C4—C5—C6	−1.4 (2)	C25—C26—C27—C28	−0.4 (2)
C9—C4—C5—C6	177.43 (16)	C31—C26—C27—C28	178.15 (15)
C4—C5—C6—C7	0.2 (2)	C26—C27—C28—C29	0.2 (2)
C8—O1—C7—C6	177.01 (16)	C30—O2—C29—C28	−179.38 (16)
C8—O1—C7—C2	−0.41 (17)	C30—O2—C29—C24	0.46 (17)
C5—C6—C7—O1	−176.25 (15)	C27—C28—C29—O2	179.60 (15)
C5—C6—C7—C2	0.8 (2)	C27—C28—C29—C24	−0.2 (2)
C3—C2—C7—O1	176.86 (14)	C25—C24—C29—O2	−179.39 (14)
C1—C2—C7—O1	0.41 (17)	C23—C24—C29—O2	−0.34 (17)
C3—C2—C7—C6	−0.6 (2)	C25—C24—C29—C28	0.5 (2)
C1—C2—C7—C6	−177.06 (15)	C23—C24—C29—C28	179.51 (15)
C2—C1—C8—O1	0.02 (18)	C24—C23—C30—O2	0.20 (18)
S1—C1—C8—O1	−173.89 (11)	S2—C23—C30—O2	178.61 (12)
C2—C1—C8—C15	179.88 (17)	C24—C23—C30—C37	−179.22 (17)
S1—C1—C8—C15	6.0 (3)	S2—C23—C30—C37	−0.8 (3)
C7—O1—C8—C1	0.24 (18)	C29—O2—C30—C23	−0.41 (18)
C7—O1—C8—C15	−179.66 (13)	C29—O2—C30—C37	179.13 (13)
C3—C4—C9—C14	−38.7 (2)	C25—C26—C31—C36	−148.12 (16)
C5—C4—C9—C14	142.52 (17)	C27—C26—C31—C36	33.3 (2)
C3—C4—C9—C10	140.75 (17)	C25—C26—C31—C32	32.8 (2)
C5—C4—C9—C10	−38.1 (2)	C27—C26—C31—C32	−145.73 (16)
C14—C9—C10—C11	0.8 (3)	C36—C31—C32—C33	−0.6 (2)
C4—C9—C10—C11	−178.60 (17)	C26—C31—C32—C33	178.51 (15)
C9—C10—C11—C12	−0.6 (3)	C31—C32—C33—C34	0.4 (2)
C10—C11—C12—F1	179.49 (16)	C32—C33—C34—F2	−179.14 (15)
C10—C11—C12—C13	−0.3 (3)	C32—C33—C34—C35	0.2 (3)
F1—C12—C13—C14	−178.87 (16)	F2—C34—C35—C36	178.78 (15)
C11—C12—C13—C14	0.9 (3)	C33—C34—C35—C36	−0.5 (3)
C12—C13—C14—C9	−0.6 (3)	C34—C35—C36—C31	0.3 (2)
C10—C9—C14—C13	−0.2 (3)	C32—C31—C36—C35	0.2 (2)
C4—C9—C14—C13	179.24 (16)	C26—C31—C36—C35	−178.87 (15)
C1—C8—C15—C20	−149.90 (19)	C23—C30—C37—C42	158.75 (18)
O1—C8—C15—C20	30.0 (2)	O2—C30—C37—C42	−20.6 (2)
C1—C8—C15—C16	32.7 (3)	C23—C30—C37—C38	−22.0 (3)
O1—C8—C15—C16	−147.39 (15)	O2—C30—C37—C38	158.57 (15)
C20—C15—C16—C17	0.5 (2)	C42—C37—C38—C39	0.4 (2)
C8—C15—C16—C17	177.92 (15)	C30—C37—C38—C39	−178.86 (16)
C15—C16—C17—C18	0.1 (3)	C37—C38—C39—C40	0.6 (3)
C16—C17—C18—C19	−0.8 (2)	C38—C39—C40—C41	−1.3 (3)
C16—C17—C18—C21	178.26 (16)	C38—C39—C40—C43	178.95 (17)
C17—C18—C19—C20	0.9 (2)	C39—C40—C41—C42	1.1 (3)
C21—C18—C19—C20	−178.14 (16)	C43—C40—C41—C42	−179.22 (17)
C18—C19—C20—C15	−0.3 (3)	C40—C41—C42—C37	−0.1 (3)
C16—C15—C20—C19	−0.4 (2)	C38—C37—C42—C41	−0.6 (2)
C8—C15—C20—C19	−177.87 (15)	C30—C37—C42—C41	178.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···F2i	0.95	2.43	3.267 (2)	147
C44—H44C···F1ii	0.98	2.52	3.359 (2)	143
C32—H32···Cg1iii	0.95	2.69	3.465 (2)	139
C36—H36···Cg1iv	0.95	2.67	3.468 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 4-methyl­phenyl ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯F2i	0.95	2.43	3.267 (2)	147
C44—H44C⋯F1ii	0.98	2.52	3.359 (2)	143
C32—H32⋯Cg1iii	0.95	2.69	3.465 (2)	139
C36—H36⋯Cg1iv	0.95	2.67	3.468 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .