Crystal structure of racemic [(1R,2S,3R,4S,6S)-2,6-bis­(furan-2-yl)-4-hy­droxy-4-(thio­phen-2-yl)cyclo­hexane-1,3-di­yl]bis­(thio­phen-2-yl­methanone)

The central cyclo­hexane ring has a chair conformation. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds and C—H...π inter­actions, forming layers parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.066
• wR factor = 0.204
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S2     --  C16     ..        8.5 s.u.

Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    --  C27     ..        5.3 s.u.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00467 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.698 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           8 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.10 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O2A    --  C15A    ..        6.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         17 Note
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C3      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C5      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C6      (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          6 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           7 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2003).

[(1R,2S,3R,4S,6S)-2,6-Bis(furan-2-yl)-4-hydroxy-4-(thiophen-2-yl)cyclohexane-1,3-diyl]bis(thiophen-2-ylmethanone)

Crystal data

C28H22O5S3	F(000) = 1112
Mr = 534.64	Dx = 1.410 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9982 reflections
a = 14.0915 (11) Å	θ = 3.1–28.2°
b = 15.8984 (12) Å	µ = 0.33 mm^−1
c = 11.2964 (7) Å	T = 296 K
β = 95.421 (2)°	Prism, colourless
V = 2519.4 (3) Å^3	0.19 × 0.17 × 0.13 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	3960 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.070
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 28.4°, θmin = 3.1°
Tmin = 0.597, Tmax = 0.746	h = −18→18
52585 measured reflections	k = −21→21
6252 independent reflections	l = −15→13

Refinement

Refinement on F^2	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.204	w = 1/[σ^2(Fo^2) + (0.101P)^2 + 2.3401P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
6252 reflections	Δρmax = 0.75 e Å^−3
338 parameters	Δρmin = −0.74 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	−0.10680 (6)	0.34243 (6)	0.32727 (9)	0.0528 (3)
S2	0.57614 (7)	0.33394 (7)	0.55457 (10)	0.0661 (4)
S3	0.38176 (6)	−0.03610 (5)	0.49813 (8)	0.0497 (3)
O1	0.06307 (16)	0.33764 (15)	0.50045 (19)	0.0468 (7)
O2A	0.1462 (2)	0.51774 (19)	0.4184 (3)	0.0541 (10)	0.832 (5)
O2B	0.2243 (12)	0.4730 (9)	0.2304 (15)	0.0541 (10)	0.168 (5)
O3A	0.3783 (2)	0.30198 (19)	0.6008 (2)	0.0419 (8)	0.832 (5)
O3B	0.2474 (13)	0.4000 (12)	0.5522 (11)	0.050 (5)	0.168 (5)
O4	0.37016 (18)	0.13400 (15)	0.59929 (19)	0.0516 (8)
O5	0.16291 (18)	0.14210 (14)	0.2732 (2)	0.0522 (8)
C1	0.2479 (2)	0.38831 (18)	0.4265 (3)	0.0354 (9)
C2	0.3529 (2)	0.37285 (18)	0.4141 (3)	0.0360 (9)
C3	0.3902 (2)	0.29228 (18)	0.4759 (2)	0.0339 (8)
C4	0.33066 (19)	0.21646 (17)	0.4248 (2)	0.0302 (8)
C5	0.22355 (19)	0.23054 (17)	0.4381 (2)	0.0317 (8)
C6	0.18765 (19)	0.31239 (16)	0.3769 (2)	0.0304 (8)
C7	0.0835 (2)	0.32507 (17)	0.3991 (3)	0.0335 (8)
C8	0.0088 (2)	0.32100 (18)	0.3002 (3)	0.0354 (9)
C9	0.0139 (2)	0.3006 (2)	0.1833 (3)	0.0433 (10)
C10	−0.0750 (3)	0.3032 (2)	0.1164 (3)	0.0578 (12)
C11	−0.1458 (3)	0.3250 (2)	0.1826 (4)	0.0592 (14)
C12A	0.2159 (3)	0.46624 (16)	0.3713 (3)	0.0372 (10)	0.832 (5)
C12B	0.2063 (16)	0.4706 (10)	0.3519 (15)	0.0372 (10)	0.168 (5)
C13A	0.2394 (3)	0.5031 (3)	0.2634 (3)	0.0602 (17)	0.832 (5)
C13B	0.1550 (17)	0.5444 (12)	0.3766 (17)	0.0602 (17)	0.168 (5)
C14A	0.1842 (3)	0.5774 (2)	0.2437 (4)	0.089 (3)	0.832 (5)
C14B	0.1413 (19)	0.5924 (11)	0.270 (2)	0.089 (3)	0.168 (5)
C15A	0.1266 (3)	0.58644 (17)	0.3395 (4)	0.095 (3)	0.832 (5)
C15B	0.1841 (17)	0.5483 (12)	0.1800 (16)	0.095 (3)	0.168 (5)
C16	0.4946 (2)	0.28136 (19)	0.4597 (3)	0.0368 (9)
C17	0.5386 (2)	0.2391 (2)	0.3737 (3)	0.0446 (10)
C18	0.6395 (3)	0.2524 (3)	0.3902 (4)	0.0607 (14)
C19	0.6665 (3)	0.3005 (3)	0.4807 (4)	0.0648 (15)
C20	0.3597 (2)	0.13466 (19)	0.4899 (3)	0.0349 (9)
C21	0.3687 (2)	0.05818 (18)	0.4227 (3)	0.0364 (9)
C22	0.3728 (3)	0.0465 (2)	0.3024 (3)	0.0470 (11)
C23	0.3884 (3)	−0.0380 (2)	0.2741 (4)	0.0588 (14)
C24	0.3939 (3)	−0.0894 (2)	0.3709 (4)	0.0564 (13)
C25	0.1672 (2)	0.15642 (18)	0.3943 (3)	0.0364 (9)
C26	0.1219 (3)	0.0946 (2)	0.4462 (4)	0.0583 (14)
C27	0.0863 (3)	0.0390 (2)	0.3511 (4)	0.0651 (14)
C28	0.1138 (3)	0.0694 (3)	0.2513 (4)	0.0681 (16)
H1A	0.237 (5)	0.395 (4)	0.511 (2)	0.0500*	0.832 (5)
H1B	0.38 (2)	0.310 (18)	0.557 (10)	0.0500*	0.168 (5)
H2A	0.38950	0.42030	0.44750	0.0430*
H2B	0.36240	0.36950	0.33030	0.0430*
H3A	0.39870	0.26000	0.63700	0.0630*	0.832 (5)
H3B	0.26770	0.35740	0.58690	0.0750*	0.168 (5)
H4	0.33970	0.21010	0.34030	0.0360*
H5	0.21640	0.23630	0.52310	0.0380*
H6	0.19240	0.30770	0.29120	0.0370*
H9	0.07030	0.28640	0.15160	0.0520*
H10	−0.08410	0.29140	0.03550	0.0690*
H11	−0.20920	0.32990	0.15220	0.0710*
H13A	0.28330	0.48230	0.21420	0.0720*	0.832 (5)
H13B	0.13400	0.55880	0.44960	0.0720*	0.168 (5)
H14A	0.18560	0.61380	0.17940	0.1060*	0.832 (5)
H14B	0.10970	0.64380	0.26150	0.1060*	0.168 (5)
H15A	0.08360	0.62980	0.34890	0.1140*	0.832 (5)
H15B	0.18560	0.56560	0.10150	0.1140*	0.168 (5)
H17	0.50730	0.20670	0.31360	0.0540*
H18	0.68180	0.22900	0.34100	0.0730*
H19	0.72980	0.31490	0.50210	0.0780*
H22	0.36600	0.08960	0.24650	0.0560*
H23	0.39440	−0.05700	0.19730	0.0710*
H24	0.40330	−0.14720	0.36740	0.0670*
H26	0.11480	0.08860	0.52680	0.0700*
H27	0.05050	−0.00950	0.35890	0.0780*
H28	0.10130	0.04470	0.17690	0.0820*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0311 (4)	0.0639 (6)	0.0647 (6)	0.0092 (4)	0.0107 (4)	0.0048 (4)
S2	0.0504 (6)	0.0790 (7)	0.0673 (7)	−0.0109 (5)	−0.0031 (5)	0.0003 (5)
S3	0.0463 (5)	0.0395 (4)	0.0629 (6)	0.0047 (3)	0.0033 (4)	0.0151 (4)
O1	0.0406 (12)	0.0624 (14)	0.0392 (12)	0.0037 (11)	0.0140 (10)	−0.0035 (10)
O2A	0.0456 (16)	0.0549 (18)	0.064 (2)	0.0046 (14)	0.0166 (14)	−0.0075 (15)
O2B	0.0456 (16)	0.0549 (18)	0.064 (2)	0.0046 (14)	0.0166 (14)	−0.0075 (15)
O3A	0.0450 (15)	0.0512 (16)	0.0295 (13)	0.0019 (12)	0.0033 (13)	−0.0089 (13)
O3B	0.055 (9)	0.060 (9)	0.035 (7)	0.003 (7)	0.007 (7)	−0.011 (8)
O4	0.0655 (16)	0.0536 (14)	0.0353 (12)	0.0054 (12)	0.0029 (11)	0.0087 (10)
O5	0.0627 (16)	0.0415 (12)	0.0497 (13)	−0.0028 (11)	−0.0083 (11)	−0.0046 (10)
C1	0.0337 (15)	0.0335 (14)	0.0395 (16)	−0.0014 (12)	0.0065 (13)	−0.0067 (12)
C2	0.0298 (14)	0.0328 (14)	0.0454 (17)	−0.0019 (11)	0.0034 (12)	−0.0019 (12)
C3	0.0315 (14)	0.0365 (15)	0.0335 (15)	−0.0007 (11)	0.0028 (12)	−0.0015 (12)
C4	0.0284 (14)	0.0320 (14)	0.0303 (14)	0.0006 (11)	0.0032 (11)	−0.0003 (11)
C5	0.0306 (14)	0.0325 (14)	0.0322 (14)	0.0012 (11)	0.0044 (11)	0.0010 (11)
C6	0.0282 (14)	0.0313 (13)	0.0325 (14)	0.0007 (11)	0.0067 (11)	−0.0026 (11)
C7	0.0309 (14)	0.0301 (14)	0.0403 (16)	0.0012 (11)	0.0084 (12)	0.0005 (11)
C8	0.0278 (14)	0.0330 (14)	0.0458 (17)	0.0023 (11)	0.0061 (12)	0.0022 (12)
C9	0.0369 (16)	0.0456 (18)	0.0470 (18)	0.0050 (14)	0.0026 (14)	−0.0055 (14)
C10	0.056 (2)	0.059 (2)	0.055 (2)	0.0027 (18)	−0.0126 (18)	−0.0101 (17)
C11	0.0371 (19)	0.059 (2)	0.078 (3)	0.0043 (16)	−0.0125 (18)	0.0010 (19)
C12A	0.0323 (18)	0.0281 (14)	0.051 (2)	0.0009 (12)	0.0032 (16)	−0.0054 (14)
C12B	0.0323 (18)	0.0281 (14)	0.051 (2)	0.0009 (12)	0.0032 (16)	−0.0054 (14)
C13A	0.060 (3)	0.052 (3)	0.070 (3)	0.014 (2)	0.014 (2)	0.022 (2)
C13B	0.060 (3)	0.052 (3)	0.070 (3)	0.014 (2)	0.014 (2)	0.022 (2)
C14A	0.069 (4)	0.054 (3)	0.137 (6)	−0.006 (3)	−0.020 (4)	0.041 (3)
C14B	0.069 (4)	0.054 (3)	0.137 (6)	−0.006 (3)	−0.020 (4)	0.041 (3)
C15A	0.063 (4)	0.047 (3)	0.167 (7)	0.011 (3)	−0.032 (4)	−0.013 (4)
C15B	0.063 (4)	0.047 (3)	0.167 (7)	0.011 (3)	−0.032 (4)	−0.013 (4)
C16	0.0291 (14)	0.0404 (16)	0.0402 (16)	−0.0010 (12)	0.0001 (12)	0.0064 (12)
C17	0.0301 (16)	0.0478 (18)	0.057 (2)	0.0030 (13)	0.0097 (14)	0.0030 (15)
C18	0.0379 (19)	0.067 (2)	0.080 (3)	0.0084 (17)	0.0205 (18)	0.017 (2)
C19	0.0372 (19)	0.078 (3)	0.077 (3)	−0.0060 (18)	−0.0054 (18)	0.025 (2)
C20	0.0290 (14)	0.0395 (15)	0.0360 (16)	−0.0002 (12)	0.0028 (12)	0.0034 (12)
C21	0.0291 (14)	0.0351 (15)	0.0446 (17)	0.0043 (12)	0.0015 (12)	0.0058 (12)
C22	0.057 (2)	0.0389 (17)	0.0451 (18)	0.0042 (15)	0.0043 (15)	0.0027 (14)
C23	0.069 (3)	0.046 (2)	0.062 (2)	0.0062 (18)	0.0095 (19)	−0.0109 (17)
C24	0.049 (2)	0.0344 (17)	0.085 (3)	0.0054 (15)	0.0028 (18)	0.0012 (17)
C25	0.0279 (14)	0.0341 (14)	0.0469 (17)	0.0036 (12)	0.0027 (12)	0.0012 (12)
C26	0.053 (2)	0.0427 (19)	0.083 (3)	−0.0021 (16)	0.0257 (19)	0.0041 (18)
C27	0.057 (2)	0.0389 (19)	0.099 (3)	−0.0146 (17)	0.005 (2)	−0.007 (2)
C28	0.070 (3)	0.049 (2)	0.081 (3)	−0.0066 (19)	−0.016 (2)	−0.010 (2)

Geometric parameters (Å, º)

S1—C8	1.720 (3)	C14A—C15A	1.420 (6)
S1—C11	1.697 (5)	C14B—C15B	1.42 (3)
S2—C16	1.713 (3)	C16—C17	1.376 (4)
S2—C19	1.674 (4)	C17—C18	1.432 (5)
S3—C21	1.725 (3)	C18—C19	1.304 (6)
S3—C24	1.691 (4)	C20—C21	1.445 (4)
O1—C7	1.223 (4)	C21—C22	1.378 (5)
O2A—C12A	1.420 (5)	C22—C23	1.403 (5)
O2A—C15A	1.420 (5)	C23—C24	1.361 (6)
O2B—C12B	1.42 (2)	C25—C26	1.337 (5)
O2B—C15B	1.42 (2)	C26—C27	1.444 (6)
O3A—C3	1.445 (3)	C27—C28	1.318 (6)
O3B—C1	1.433 (13)	C1—H1A	0.99 (3)
O4—C20	1.231 (4)	C2—H2A	0.9700
O5—C25	1.383 (4)	C2—H2B	0.9700
O5—C28	1.358 (5)	C3—H1B	0.98 (16)
O3A—H3A	0.8200	C4—H4	0.9800
O3B—H3B	0.8200	C5—H5	0.9800
C1—C2	1.519 (4)	C6—H6	0.9800
C1—C12B	1.635 (17)	C9—H9	0.9300
C1—C12A	1.440 (4)	C10—H10	0.9300
C1—C6	1.550 (4)	C11—H11	0.9300
C2—C3	1.528 (4)	C13A—H13A	0.9300
C3—C16	1.510 (4)	C13B—H13B	0.9300
C3—C4	1.549 (4)	C14A—H14A	0.9300
C4—C5	1.547 (4)	C14B—H14B	0.9300
C4—C20	1.531 (4)	C15A—H15A	0.9300
C5—C6	1.537 (4)	C15B—H15B	0.9300
C5—C25	1.480 (4)	C17—H17	0.9300
C6—C7	1.526 (4)	C18—H18	0.9300
C7—C8	1.462 (4)	C19—H19	0.9300
C8—C9	1.368 (5)	C22—H22	0.9300
C9—C10	1.401 (5)	C23—H23	0.9300
C10—C11	1.348 (6)	C24—H24	0.9300
C12A—C13A	1.420 (5)	C26—H26	0.9300
C12B—C13B	1.42 (3)	C27—H27	0.9300
C13A—C14A	1.420 (6)	C28—H28	0.9300
C13B—C14B	1.42 (3)
C8—S1—C11	91.29 (19)	C21—C22—C23	112.1 (3)
C16—S2—C19	91.72 (19)	C22—C23—C24	113.0 (4)
C21—S3—C24	91.73 (17)	S3—C24—C23	112.3 (3)
C12A—O2A—C15A	108.0 (3)	O5—C25—C26	109.6 (3)
C12B—O2B—C15B	108.0 (15)	C5—C25—C26	134.6 (3)
C25—O5—C28	107.1 (3)	O5—C25—C5	115.7 (2)
C3—O3A—H3A	109.00	C25—C26—C27	105.7 (4)
C1—O3B—H3B	109.00	C26—C27—C28	107.6 (3)
O3B—C1—C12B	111.8 (10)	O5—C28—C27	110.0 (4)
O3B—C1—C2	102.0 (8)	C2—C1—H1A	110 (4)
O3B—C1—C6	113.9 (8)	C6—C1—H1A	108 (4)
C2—C1—C12B	112.8 (8)	C12A—C1—H1A	105 (4)
C6—C1—C12A	112.0 (3)	C1—C2—H2A	109.00
C6—C1—C12B	106.2 (7)	C1—C2—H2B	109.00
C2—C1—C12A	111.5 (3)	C3—C2—H2A	109.00
C2—C1—C6	110.2 (2)	C3—C2—H2B	109.00
C1—C2—C3	112.9 (2)	H2A—C2—H2B	108.00
O3A—C3—C2	106.9 (2)	C2—C3—H1B	96 (14)
C2—C3—C4	109.4 (2)	C4—C3—H1B	117 (15)
O3A—C3—C4	109.8 (2)	C16—C3—H1B	112 (17)
O3A—C3—C16	109.6 (2)	C3—C4—H4	109.00
C4—C3—C16	111.4 (2)	C5—C4—H4	109.00
C2—C3—C16	109.8 (2)	C20—C4—H4	109.00
C3—C4—C20	111.8 (2)	C4—C5—H5	107.00
C3—C4—C5	110.5 (2)	C6—C5—H5	108.00
C5—C4—C20	107.2 (2)	C25—C5—H5	107.00
C4—C5—C25	110.5 (2)	C1—C6—H6	109.00
C4—C5—C6	111.2 (2)	C5—C6—H6	109.00
C6—C5—C25	112.4 (2)	C7—C6—H6	109.00
C5—C6—C7	108.6 (2)	C8—C9—H9	124.00
C1—C6—C7	109.9 (2)	C10—C9—H9	124.00
C1—C6—C5	110.6 (2)	C9—C10—H10	124.00
O1—C7—C6	119.4 (3)	C11—C10—H10	124.00
O1—C7—C8	120.4 (3)	S1—C11—H11	124.00
C6—C7—C8	120.2 (3)	C10—C11—H11	124.00
S1—C8—C7	118.8 (2)	C12A—C13A—H13A	126.00
C7—C8—C9	130.4 (3)	C14A—C13A—H13A	126.00
S1—C8—C9	110.8 (2)	C12B—C13B—H13B	126.00
C8—C9—C10	112.8 (3)	C14B—C13B—H13B	126.00
C9—C10—C11	112.3 (3)	C15A—C14A—H14A	126.00
S1—C11—C10	112.8 (3)	C13A—C14A—H14A	126.00
O2A—C12A—C13A	108.0 (3)	C15B—C14B—H14B	126.00
O2A—C12A—C1	122.2 (3)	C13B—C14B—H14B	126.00
C1—C12A—C13A	129.7 (3)	O2A—C15A—H15A	126.00
O2B—C12B—C1	115.6 (13)	C14A—C15A—H15A	126.00
O2B—C12B—C13B	108.0 (15)	C14B—C15B—H15B	126.00
C1—C12B—C13B	136.4 (15)	O2B—C15B—H15B	126.00
C12A—C13A—C14A	108.0 (3)	C18—C17—H17	125.00
C12B—C13B—C14B	107.9 (17)	C16—C17—H17	125.00
C13A—C14A—C15A	108.0 (3)	C17—C18—H18	123.00
C13B—C14B—C15B	108.0 (17)	C19—C18—H18	123.00
O2A—C15A—C14A	108.0 (3)	S2—C19—H19	123.00
O2B—C15B—C14B	108.1 (16)	C18—C19—H19	123.00
S2—C16—C17	111.1 (2)	C23—C22—H22	124.00
C3—C16—C17	130.6 (3)	C21—C22—H22	124.00
S2—C16—C3	118.2 (2)	C22—C23—H23	124.00
C16—C17—C18	110.1 (3)	C24—C23—H23	123.00
C17—C18—C19	113.7 (4)	S3—C24—H24	124.00
S2—C19—C18	113.4 (3)	C23—C24—H24	124.00
O4—C20—C4	119.4 (3)	C27—C26—H26	127.00
O4—C20—C21	120.8 (3)	C25—C26—H26	127.00
C4—C20—C21	119.7 (3)	C26—C27—H27	126.00
S3—C21—C20	118.8 (3)	C28—C27—H27	126.00
S3—C21—C22	110.9 (2)	C27—C28—H28	125.00
C20—C21—C22	130.2 (3)	O5—C28—H28	125.00
C11—S1—C8—C7	−179.5 (2)	C3—C4—C20—O4	46.3 (3)
C11—S1—C8—C9	−0.6 (3)	C3—C4—C5—C6	57.1 (2)
C8—S1—C11—C10	0.5 (3)	C5—C4—C20—O4	−75.0 (3)
C19—S2—C16—C3	−175.7 (3)	C20—C4—C5—C25	−55.4 (3)
C19—S2—C16—C17	0.2 (3)	C4—C5—C6—C7	−176.9 (2)
C16—S2—C19—C18	−0.3 (4)	C6—C5—C25—O5	57.1 (3)
C24—S3—C21—C22	0.7 (3)	C6—C5—C25—C26	−127.6 (4)
C24—S3—C21—C20	−176.8 (3)	C25—C5—C6—C7	58.7 (3)
C21—S3—C24—C23	0.0 (3)	C25—C5—C6—C1	179.3 (2)
C15A—O2A—C12A—C1	−176.4 (3)	C4—C5—C25—O5	−67.7 (3)
C12A—O2A—C15A—C14A	0.0 (4)	C4—C5—C6—C1	−56.2 (3)
C15A—O2A—C12A—C13A	0.0 (4)	C4—C5—C25—C26	107.5 (4)
C28—O5—C25—C5	176.3 (3)	C1—C6—C7—O1	−55.6 (3)
C28—O5—C25—C26	−0.2 (4)	C5—C6—C7—O1	65.5 (3)
C25—O5—C28—C27	1.1 (4)	C5—C6—C7—C8	−113.6 (3)
C6—C1—C12A—O2A	90.7 (4)	C1—C6—C7—C8	125.3 (3)
C2—C1—C12A—C13A	39.2 (5)	C6—C7—C8—C9	5.6 (5)
C2—C1—C6—C5	55.4 (3)	O1—C7—C8—C9	−173.5 (3)
C6—C1—C12A—C13A	−84.9 (5)	O1—C7—C8—S1	5.1 (4)
C12A—C1—C6—C7	−59.9 (3)	C6—C7—C8—S1	−175.8 (2)
C12A—C1—C6—C5	−179.8 (3)	S1—C8—C9—C10	0.6 (4)
C12A—C1—C2—C3	177.8 (3)	C7—C8—C9—C10	179.3 (3)
C2—C1—C6—C7	175.3 (2)	C8—C9—C10—C11	−0.2 (4)
C2—C1—C12A—O2A	−145.2 (3)	C9—C10—C11—S1	−0.3 (4)
C6—C1—C2—C3	−57.1 (3)	C1—C12A—C13A—C14A	176.0 (4)
C1—C2—C3—C16	−180.0 (3)	O2A—C12A—C13A—C14A	0.0 (4)
C1—C2—C3—O3A	−61.2 (3)	C12A—C13A—C14A—C15A	0.0 (5)
C1—C2—C3—C4	57.5 (3)	C13A—C14A—C15A—O2A	0.0 (4)
C2—C3—C4—C5	−56.4 (3)	S2—C16—C17—C18	−0.1 (4)
C2—C3—C16—C17	−92.0 (4)	C3—C16—C17—C18	175.2 (3)
O3A—C3—C4—C20	−58.7 (3)	C16—C17—C18—C19	−0.1 (5)
C2—C3—C16—S2	83.0 (3)	C17—C18—C19—S2	0.2 (5)
O3A—C3—C4—C5	60.6 (3)	O4—C20—C21—C22	−170.1 (4)
C16—C3—C4—C20	62.9 (3)	O4—C20—C21—S3	6.8 (4)
C2—C3—C4—C20	−175.6 (2)	C4—C20—C21—C22	13.8 (5)
O3A—C3—C16—C17	150.9 (3)	C4—C20—C21—S3	−169.3 (2)
O3A—C3—C16—S2	−34.1 (3)	S3—C21—C22—C23	−1.3 (4)
C4—C3—C16—C17	29.3 (4)	C20—C21—C22—C23	175.8 (3)
C4—C3—C16—S2	−155.75 (19)	C21—C22—C23—C24	1.3 (5)
C16—C3—C4—C5	−177.9 (2)	C22—C23—C24—S3	−0.8 (5)
C3—C4—C5—C25	−177.4 (2)	O5—C25—C26—C27	−0.7 (4)
C20—C4—C5—C6	179.2 (2)	C5—C25—C26—C27	−176.2 (3)
C5—C4—C20—C21	101.2 (3)	C25—C26—C27—C28	1.4 (5)
C3—C4—C20—C21	−137.6 (3)	C26—C27—C28—O5	−1.5 (5)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the S1/C8–C11 and S2/C16–C19 thiophene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3A···O4	0.82	2.08	2.673 (4)	129
C5—H5···O3A	0.98	2.59	2.944 (4)	102
C22—H22···O3A^i	0.93	2.40	3.321 (4)	170
C24—H24···Cg2^ii	0.93	2.95	3.650 (4)	133
C27—H27···Cg1^iii	0.93	2.89	3.612 (4)	135
C14B—H14B···Cg1^iv	0.93	2.87	3.772 (19)	163

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x, y−1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2.