Syntheses and crystal structure of a (2,6-diiso­propyldi­naphtho­[2,1-d:1′,2′-f][1,3]dithiepin-4-yl)(phen­yl)methanol atropisomer

The mol­ecular and crystal structure is reported for the major diastereoisomer formed in a sterically hindered reaction of a substituted di­naphtho­dithiepine. The structure lends support to a reaction mechanism and transition state postulated to explain the experimentally determined preferential formation of this diastereoisomer over the minor component.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 168 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.127
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.134
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00495 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -7.151 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.473 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.134 Report
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.68 mm
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.22 Why ?
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C201     -C209     .       1.42 Ang.
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         90 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip 2010).

(2,6-Diisopropyldinaphtho[2,1-d:1',2'-f][1,3]dithiepin-4-yl)(phenyl)methanol atropisomer

Crystal data

C34H32OS2	Dx = 1.221 Mg m^−3
Mr = 520.71	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5483 reflections
a = 11.874 (4) Å	θ = 2.2–26.3°
b = 19.579 (7) Å	µ = 0.21 mm^−1
c = 24.374 (9) Å	T = 168 K
V = 5666 (3) Å^3	Plate, pale yellow
Z = 8	0.68 × 0.40 × 0.13 mm
F(000) = 2208

Data collection

Bruker SMART CCD diffractometer	3354 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.134
ω scans	θmax = 26.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
Tmin = 0.835, Tmax = 1.000	k = −11→24
68261 measured reflections	l = −30→30
5679 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0365P)^2 + 6.2206P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
5679 reflections	Δρmax = 0.33 e Å^−3
339 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.44124 (7)	0.28091 (4)	0.43352 (3)	0.03261 (19)
S2	0.43855 (7)	0.41835 (4)	0.49632 (3)	0.03191 (19)
O2	0.19441 (19)	0.27784 (11)	0.47083 (10)	0.0472 (6)
H2O	0.239891	0.250347	0.456374	0.071*
C101	0.5406 (3)	0.38957 (15)	0.38412 (12)	0.0314 (7)
C102	0.4540 (2)	0.34209 (14)	0.37906 (11)	0.0304 (7)
C103	0.3799 (3)	0.34092 (15)	0.33207 (12)	0.0316 (7)
C111	0.2886 (3)	0.28677 (16)	0.32557 (12)	0.0366 (7)
H111	0.262395	0.273779	0.363137	0.044*
C112	0.3394 (3)	0.22282 (18)	0.29887 (17)	0.0614 (11)
H11D	0.280968	0.187848	0.294893	0.092*
H11E	0.400322	0.205180	0.322025	0.092*
H11F	0.369497	0.234602	0.262637	0.092*
C113	0.1849 (3)	0.3108 (2)	0.29280 (15)	0.0574 (10)
H11A	0.125411	0.276258	0.295201	0.086*
H11B	0.205896	0.317552	0.254296	0.086*
H11C	0.157338	0.354035	0.308078	0.086*
C104	0.3978 (3)	0.38892 (15)	0.29172 (12)	0.0363 (8)
H104	0.350863	0.388457	0.260141	0.044*
C105	0.4996 (3)	0.48813 (17)	0.25314 (14)	0.0503 (10)
H105	0.452517	0.487305	0.221655	0.060*
C106	0.5824 (4)	0.53643 (19)	0.25746 (15)	0.0609 (11)
H106	0.593005	0.568410	0.228608	0.073*
C107	0.6523 (3)	0.53936 (18)	0.30425 (14)	0.0528 (10)
H107	0.708449	0.573768	0.306929	0.063*
C108	0.6396 (3)	0.49259 (16)	0.34607 (13)	0.0414 (8)
H108	0.686723	0.495194	0.377498	0.050*
C109	0.5563 (3)	0.44036 (15)	0.34254 (12)	0.0336 (7)
C110	0.4837 (3)	0.43908 (16)	0.29560 (12)	0.0370 (8)
C201	0.6210 (3)	0.38596 (14)	0.43239 (12)	0.0300 (7)
C202	0.5861 (2)	0.40046 (14)	0.48581 (12)	0.0303 (7)
C203	0.6628 (3)	0.40156 (14)	0.53151 (12)	0.0306 (7)
C211	0.6236 (3)	0.42082 (15)	0.58962 (12)	0.0354 (7)
H211	0.561121	0.454716	0.585743	0.042*
C212	0.5756 (3)	0.35802 (17)	0.61924 (13)	0.0485 (9)
H21A	0.551202	0.371053	0.656198	0.073*
H21B	0.633787	0.322683	0.621808	0.073*
H21C	0.511081	0.340249	0.598607	0.073*
C213	0.7165 (3)	0.45444 (18)	0.62422 (14)	0.0519 (9)
H21D	0.746040	0.494416	0.604760	0.078*
H21E	0.777538	0.421601	0.630341	0.078*
H21F	0.685264	0.468733	0.659612	0.078*
C204	0.7736 (3)	0.38353 (14)	0.52109 (12)	0.0324 (7)
H204	0.826086	0.384480	0.550514	0.039*
C205	0.9258 (3)	0.34162 (15)	0.45912 (13)	0.0362 (7)
H205	0.976911	0.340143	0.489093	0.043*
C206	0.9616 (3)	0.32265 (16)	0.40766 (14)	0.0435 (8)
H206	1.037199	0.308329	0.402203	0.052*
C207	0.8859 (3)	0.32443 (18)	0.36282 (14)	0.0464 (9)
H207	0.911225	0.311034	0.327445	0.056*
C208	0.7764 (3)	0.34529 (16)	0.36978 (13)	0.0411 (8)
H208	0.726915	0.346307	0.339167	0.049*
C209	0.7360 (3)	0.36552 (14)	0.42274 (12)	0.0314 (7)
C210	0.8123 (3)	0.36355 (14)	0.46790 (12)	0.0323 (7)
C1	0.3767 (3)	0.33266 (15)	0.48761 (12)	0.0325 (7)
H1	0.387627	0.307626	0.522978	0.039*
C2	0.2491 (3)	0.34195 (15)	0.47961 (12)	0.0344 (7)
H2	0.236419	0.371453	0.446697	0.041*
C3	0.1923 (3)	0.37540 (16)	0.52906 (13)	0.0373 (8)
C4	0.1482 (3)	0.44076 (17)	0.52523 (16)	0.0495 (9)
H4	0.159453	0.466572	0.492683	0.059*
C5	0.0874 (3)	0.4691 (2)	0.5686 (2)	0.0727 (14)
H5	0.058165	0.514127	0.565737	0.087*
C6	0.0700 (4)	0.4318 (3)	0.6153 (2)	0.0806 (16)
H6	0.026471	0.450263	0.644453	0.097*
C7	0.1160 (4)	0.3668 (3)	0.62003 (17)	0.0747 (14)
H7	0.105793	0.341571	0.652939	0.090*
C8	0.1771 (3)	0.3385 (2)	0.57685 (14)	0.0536 (10)
H8	0.208080	0.293923	0.580218	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0432 (5)	0.0266 (4)	0.0280 (4)	0.0020 (4)	0.0017 (4)	0.0016 (3)
S2	0.0340 (4)	0.0287 (4)	0.0330 (4)	0.0016 (3)	0.0011 (4)	−0.0015 (3)
O2	0.0445 (14)	0.0360 (12)	0.0610 (16)	−0.0023 (11)	0.0005 (12)	−0.0121 (12)
C101	0.0372 (18)	0.0312 (16)	0.0258 (16)	0.0047 (14)	0.0016 (13)	0.0002 (12)
C102	0.0374 (18)	0.0290 (15)	0.0248 (16)	0.0053 (14)	0.0024 (14)	−0.0006 (12)
C103	0.0364 (18)	0.0324 (16)	0.0259 (16)	0.0013 (14)	0.0006 (14)	−0.0007 (13)
C111	0.0411 (19)	0.0415 (18)	0.0272 (16)	−0.0055 (15)	−0.0023 (14)	−0.0005 (14)
C112	0.066 (3)	0.047 (2)	0.071 (3)	−0.013 (2)	0.008 (2)	−0.018 (2)
C113	0.046 (2)	0.072 (3)	0.054 (2)	−0.014 (2)	−0.0098 (19)	0.009 (2)
C104	0.0447 (19)	0.0411 (18)	0.0230 (16)	−0.0018 (15)	−0.0044 (14)	0.0012 (14)
C105	0.069 (3)	0.051 (2)	0.0312 (18)	−0.015 (2)	−0.0113 (18)	0.0129 (16)
C106	0.085 (3)	0.058 (2)	0.040 (2)	−0.023 (2)	−0.004 (2)	0.0179 (18)
C107	0.061 (2)	0.053 (2)	0.045 (2)	−0.0199 (19)	0.0012 (19)	0.0107 (18)
C108	0.046 (2)	0.0446 (19)	0.0338 (18)	−0.0063 (16)	0.0009 (16)	−0.0003 (15)
C109	0.0391 (18)	0.0336 (16)	0.0281 (16)	−0.0001 (15)	0.0027 (15)	0.0000 (13)
C110	0.0453 (19)	0.0389 (18)	0.0268 (17)	−0.0035 (15)	0.0006 (15)	0.0024 (14)
C201	0.0350 (17)	0.0278 (15)	0.0271 (16)	−0.0034 (13)	−0.0043 (14)	0.0041 (13)
C202	0.0347 (18)	0.0243 (15)	0.0318 (17)	0.0003 (12)	−0.0004 (13)	0.0017 (12)
C203	0.0399 (19)	0.0225 (14)	0.0295 (16)	−0.0013 (13)	−0.0045 (14)	0.0007 (12)
C211	0.0448 (19)	0.0318 (16)	0.0295 (17)	0.0034 (15)	−0.0044 (15)	−0.0026 (13)
C212	0.066 (2)	0.046 (2)	0.0333 (19)	0.0007 (18)	0.0034 (18)	0.0020 (15)
C213	0.059 (2)	0.058 (2)	0.038 (2)	−0.0046 (19)	−0.0031 (18)	−0.0152 (17)
C204	0.0395 (19)	0.0291 (16)	0.0287 (16)	−0.0030 (14)	−0.0087 (14)	0.0020 (13)
C205	0.0345 (18)	0.0357 (17)	0.0386 (18)	−0.0013 (15)	−0.0025 (15)	0.0046 (14)
C206	0.036 (2)	0.0420 (19)	0.052 (2)	0.0065 (15)	0.0046 (17)	0.0021 (16)
C207	0.044 (2)	0.058 (2)	0.0363 (19)	0.0071 (18)	0.0030 (17)	−0.0044 (17)
C208	0.041 (2)	0.049 (2)	0.0329 (18)	0.0042 (16)	−0.0042 (15)	−0.0043 (15)
C209	0.0342 (18)	0.0299 (16)	0.0301 (17)	−0.0004 (13)	0.0011 (14)	−0.0009 (13)
C210	0.0349 (18)	0.0262 (16)	0.0358 (18)	−0.0011 (13)	−0.0020 (14)	0.0012 (13)
C1	0.0381 (18)	0.0311 (16)	0.0282 (16)	−0.0001 (14)	0.0030 (14)	−0.0022 (13)
C2	0.0397 (18)	0.0275 (16)	0.0361 (18)	0.0000 (14)	−0.0024 (14)	−0.0016 (13)
C3	0.0303 (17)	0.0368 (18)	0.045 (2)	−0.0073 (14)	0.0023 (15)	−0.0087 (15)
C4	0.041 (2)	0.0393 (19)	0.068 (3)	−0.0021 (16)	0.0074 (18)	−0.0106 (18)
C5	0.047 (3)	0.057 (3)	0.114 (4)	−0.009 (2)	0.023 (3)	−0.046 (3)
C6	0.063 (3)	0.099 (4)	0.080 (3)	−0.041 (3)	0.036 (3)	−0.059 (3)
C7	0.080 (3)	0.096 (4)	0.049 (2)	−0.049 (3)	0.016 (2)	−0.017 (2)
C8	0.058 (2)	0.059 (2)	0.044 (2)	−0.018 (2)	0.0047 (19)	−0.0076 (18)

Geometric parameters (Å, º)

S1—C102	1.794 (3)	C203—C211	1.538 (4)
S1—C1	1.831 (3)	C211—C212	1.536 (4)
S2—C202	1.805 (3)	C211—C213	1.537 (4)
S2—C1	1.844 (3)	C211—H211	1.0000
O2—C2	1.429 (3)	C212—H21A	0.9800
O2—H2O	0.8400	C212—H21B	0.9800
C101—C102	1.391 (4)	C212—H21C	0.9800
C101—C109	1.432 (4)	C213—H21D	0.9800
C101—C201	1.517 (4)	C213—H21E	0.9800
C102—C103	1.444 (4)	C213—H21F	0.9800
C103—C104	1.377 (4)	C204—C210	1.430 (4)
C103—C111	1.525 (4)	C204—H204	0.9500
C111—C112	1.535 (4)	C205—C206	1.375 (4)
C111—C113	1.542 (4)	C205—C210	1.430 (4)
C111—H111	1.0000	C205—H205	0.9500
C112—H11D	0.9800	C206—C207	1.415 (5)
C112—H11E	0.9800	C206—H206	0.9500
C112—H11F	0.9800	C207—C208	1.374 (4)
C113—H11A	0.9800	C207—H207	0.9500
C113—H11B	0.9800	C208—C209	1.433 (4)
C113—H11C	0.9800	C208—H208	0.9500
C104—C110	1.420 (4)	C209—C210	1.426 (4)
C104—H104	0.9500	C1—C2	1.538 (4)
C105—C106	1.368 (5)	C1—H1	1.0000
C105—C110	1.425 (4)	C2—C3	1.529 (4)
C105—H105	0.9500	C2—H2	1.0000
C106—C107	1.411 (5)	C3—C8	1.383 (5)
C106—H106	0.9500	C3—C4	1.386 (4)
C107—C108	1.379 (4)	C4—C5	1.395 (5)
C107—H107	0.9500	C4—H4	0.9500
C108—C109	1.425 (4)	C5—C6	1.368 (6)
C108—H108	0.9500	C5—H5	0.9500
C109—C110	1.432 (4)	C6—C7	1.389 (7)
C201—C202	1.396 (4)	C6—H6	0.9500
C201—C209	1.442 (4)	C7—C8	1.394 (5)
C202—C203	1.439 (4)	C7—H7	0.9500
C203—C204	1.386 (4)	C8—H8	0.9500
C102—S1—C1	101.47 (13)	C203—C211—H211	107.5
C202—S2—C1	101.17 (13)	C211—C212—H21A	109.5
C2—O2—H2O	109.5	C211—C212—H21B	109.5
C102—C101—C109	119.8 (3)	H21A—C212—H21B	109.5
C102—C101—C201	120.2 (3)	C211—C212—H21C	109.5
C109—C101—C201	119.9 (3)	H21A—C212—H21C	109.5
C101—C102—C103	122.1 (3)	H21B—C212—H21C	109.5
C101—C102—S1	116.3 (2)	C211—C213—H21D	109.5
C103—C102—S1	121.6 (2)	C211—C213—H21E	109.5
C104—C103—C102	117.5 (3)	H21D—C213—H21E	109.5
C104—C103—C111	120.6 (3)	C211—C213—H21F	109.5
C102—C103—C111	121.8 (3)	H21D—C213—H21F	109.5
C103—C111—C112	109.4 (3)	H21E—C213—H21F	109.5
C103—C111—C113	114.2 (3)	C203—C204—C210	122.7 (3)
C112—C111—C113	110.1 (3)	C203—C204—H204	118.6
C103—C111—H111	107.6	C210—C204—H204	118.6
C112—C111—H111	107.6	C206—C205—C210	120.6 (3)
C113—C111—H111	107.6	C206—C205—H205	119.7
C111—C112—H11D	109.5	C210—C205—H205	119.7
C111—C112—H11E	109.5	C205—C206—C207	120.1 (3)
H11D—C112—H11E	109.5	C205—C206—H206	119.9
C111—C112—H11F	109.5	C207—C206—H206	119.9
H11D—C112—H11F	109.5	C208—C207—C206	120.9 (3)
H11E—C112—H11F	109.5	C208—C207—H207	119.6
C111—C113—H11A	109.5	C206—C207—H207	119.6
C111—C113—H11B	109.5	C207—C208—C209	120.7 (3)
H11A—C113—H11B	109.5	C207—C208—H208	119.7
C111—C113—H11C	109.5	C209—C208—H208	119.7
H11A—C113—H11C	109.5	C210—C209—C208	118.4 (3)
H11B—C113—H11C	109.5	C210—C209—C201	118.9 (3)
C103—C104—C110	122.3 (3)	C208—C209—C201	122.7 (3)
C103—C104—H104	118.8	C209—C210—C204	119.2 (3)
C110—C104—H104	118.8	C209—C210—C205	119.4 (3)
C106—C105—C110	120.4 (3)	C204—C210—C205	121.4 (3)
C106—C105—H105	119.8	C2—C1—S1	112.7 (2)
C110—C105—H105	119.8	C2—C1—S2	107.4 (2)
C105—C106—C107	120.8 (3)	S1—C1—S2	114.81 (16)
C105—C106—H106	119.6	C2—C1—H1	107.2
C107—C106—H106	119.6	S1—C1—H1	107.2
C108—C107—C106	120.4 (3)	S2—C1—H1	107.2
C108—C107—H107	119.8	O2—C2—C3	107.1 (2)
C106—C107—H107	119.8	O2—C2—C1	111.3 (2)
C107—C108—C109	120.5 (3)	C3—C2—C1	112.7 (3)
C107—C108—H108	119.7	O2—C2—H2	108.6
C109—C108—H108	119.7	C3—C2—H2	108.6
C108—C109—C101	123.1 (3)	C1—C2—H2	108.6
C108—C109—C110	118.6 (3)	C8—C3—C4	119.4 (3)
C101—C109—C110	118.3 (3)	C8—C3—C2	119.8 (3)
C104—C110—C105	120.9 (3)	C4—C3—C2	120.6 (3)
C104—C110—C109	119.9 (3)	C3—C4—C5	120.8 (4)
C105—C110—C109	119.2 (3)	C3—C4—H4	119.6
C202—C201—C209	119.3 (3)	C5—C4—H4	119.6
C202—C201—C101	121.8 (3)	C6—C5—C4	119.7 (4)
C209—C201—C101	118.9 (3)	C6—C5—H5	120.1
C201—C202—C203	122.5 (3)	C4—C5—H5	120.1
C201—C202—S2	117.4 (2)	C5—C6—C7	119.9 (4)
C203—C202—S2	120.1 (2)	C5—C6—H6	120.0
C204—C203—C202	117.1 (3)	C7—C6—H6	120.0
C204—C203—C211	121.2 (3)	C6—C7—C8	120.5 (4)
C202—C203—C211	121.6 (3)	C6—C7—H7	119.8
C212—C211—C213	110.6 (3)	C8—C7—H7	119.8
C212—C211—C203	110.4 (2)	C3—C8—C7	119.7 (4)
C213—C211—C203	113.1 (3)	C3—C8—H8	120.1
C212—C211—H211	107.5	C7—C8—H8	120.1
C213—C211—H211	107.5
C109—C101—C102—C103	1.6 (4)	C201—C202—C203—C211	177.2 (3)
C201—C101—C102—C103	−176.0 (3)	S2—C202—C203—C211	−2.7 (4)
C109—C101—C102—S1	−179.7 (2)	C204—C203—C211—C212	−93.8 (3)
C201—C101—C102—S1	2.6 (4)	C202—C203—C211—C212	85.2 (3)
C1—S1—C102—C101	76.0 (2)	C204—C203—C211—C213	30.7 (4)
C1—S1—C102—C103	−105.3 (2)	C202—C203—C211—C213	−150.2 (3)
C101—C102—C103—C104	0.1 (4)	C202—C203—C204—C210	−0.9 (4)
S1—C102—C103—C104	−178.5 (2)	C211—C203—C204—C210	178.2 (3)
C101—C102—C103—C111	177.2 (3)	C210—C205—C206—C207	−0.2 (5)
S1—C102—C103—C111	−1.4 (4)	C205—C206—C207—C208	0.3 (5)
C104—C103—C111—C112	91.7 (4)	C206—C207—C208—C209	−0.2 (5)
C102—C103—C111—C112	−85.3 (4)	C207—C208—C209—C210	0.1 (5)
C104—C103—C111—C113	−32.2 (4)	C207—C208—C209—C201	−178.2 (3)
C102—C103—C111—C113	150.8 (3)	C202—C201—C209—C210	−2.7 (4)
C102—C103—C104—C110	−1.2 (4)	C101—C201—C209—C210	178.6 (3)
C111—C103—C104—C110	−178.4 (3)	C202—C201—C209—C208	175.6 (3)
C110—C105—C106—C107	−1.0 (6)	C101—C201—C209—C208	−3.0 (4)
C105—C106—C107—C108	1.2 (6)	C208—C209—C210—C204	−180.0 (3)
C106—C107—C108—C109	0.4 (5)	C201—C209—C210—C204	−1.6 (4)
C107—C108—C109—C101	178.7 (3)	C208—C209—C210—C205	0.0 (4)
C107—C108—C109—C110	−2.2 (5)	C201—C209—C210—C205	178.4 (3)
C102—C101—C109—C108	177.0 (3)	C203—C204—C210—C209	3.4 (4)
C201—C101—C109—C108	−5.4 (4)	C203—C204—C210—C205	−176.5 (3)
C102—C101—C109—C110	−2.1 (4)	C206—C205—C210—C209	0.1 (4)
C201—C101—C109—C110	175.5 (3)	C206—C205—C210—C204	−179.9 (3)
C103—C104—C110—C105	−179.8 (3)	C102—S1—C1—C2	79.4 (2)
C103—C104—C110—C109	0.7 (5)	C102—S1—C1—S2	−44.0 (2)
C106—C105—C110—C104	179.7 (3)	C202—S2—C1—C2	−164.7 (2)
C106—C105—C110—C109	−0.8 (5)	C202—S2—C1—S1	−38.5 (2)
C108—C109—C110—C104	−178.1 (3)	S1—C1—C2—O2	50.8 (3)
C101—C109—C110—C104	1.0 (4)	S2—C1—C2—O2	178.23 (19)
C108—C109—C110—C105	2.4 (5)	S1—C1—C2—C3	171.0 (2)
C101—C109—C110—C105	−178.5 (3)	S2—C1—C2—C3	−61.5 (3)
C102—C101—C201—C202	−68.8 (4)	O2—C2—C3—C8	49.5 (4)
C109—C101—C201—C202	113.6 (3)	C1—C2—C3—C8	−73.2 (4)
C102—C101—C201—C209	109.8 (3)	O2—C2—C3—C4	−125.6 (3)
C109—C101—C201—C209	−67.8 (4)	C1—C2—C3—C4	111.7 (3)
C209—C201—C202—C203	5.5 (4)	C8—C3—C4—C5	−1.0 (5)
C101—C201—C202—C203	−175.9 (3)	C2—C3—C4—C5	174.2 (3)
C209—C201—C202—S2	−174.6 (2)	C3—C4—C5—C6	−0.7 (6)
C101—C201—C202—S2	4.0 (4)	C4—C5—C6—C7	2.1 (6)
C1—S2—C202—C201	72.4 (2)	C5—C6—C7—C8	−2.0 (6)
C1—S2—C202—C203	−107.7 (2)	C4—C3—C8—C7	1.1 (5)
C201—C202—C203—C204	−3.7 (4)	C2—C3—C8—C7	−174.0 (3)
S2—C202—C203—C204	176.4 (2)	C6—C7—C8—C3	0.3 (6)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg5 are the centroids of the C3–C8 and C205–C210 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···S1	0.84	2.53	3.069 (3)	123
C111—H111···S1	1.00	2.73	3.197 (3)	109
C211—H211···S2	1.00	2.72	3.163 (3)	107
C206—H206···O2^i	0.95	2.58	3.284 (4)	132
C205—H205···Cg1^i	0.95	3.01	3.886 (4)	154
C5—H5···Cg5^ii	0.95	3.03	3.759 (4)	135

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1.