1,4-Di­phenyl-2,3-dithien-3-yl­cyclo­pentadien-1-one

The title compound, C₂₅H₁₆OS₂, (I), was synthesized via the alkali-catalysed condensation of 3,3'-thenil and 1,3-di­phenyl-2-propanone in absolute ethanol. Both 3-thienyl rings in (I) exhibit an 18.89% flip disorder. Thienyl-ring flip disorders are often observed with mol­ecules having unsubstituted terminal 3-thienyl rings [Crundwell et al. (2002). Acta Cryst. E58, o668-o670.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.132
• Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(18B)

Author response: These H18B to C25B are part of the disordered/flipped thienyl rings. They are connected to their disordered carbon counterparts by 0.93 \%A just like the hydrogens on carbons in the main fragment.

PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(20B)

Author response: These H18B to C25B are part of the disordered/flipped thienyl rings. They are connected to their disordered carbon counterparts by 0.93 \%A just like the hydrogens on carbons in the main fragment.

PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(21B)

Author response: These H18B to C25B are part of the disordered/flipped thienyl rings. They are connected to their disordered carbon counterparts by 0.93 \%A just like the hydrogens on carbons in the main fragment.

PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(22B)

Author response: These H18B to C25B are part of the disordered/flipped thienyl rings. They are connected to their disordered carbon counterparts by 0.93 \%A just like the hydrogens on carbons in the main fragment.

PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(24B)

Author response: These H18B to C25B are part of the disordered/flipped thienyl rings. They are connected to their disordered carbon counterparts by 0.93 \%A just like the hydrogens on carbons in the main fragment.

PLAT_305  Alert A Isolated Hydrogen Atom (Outside Bond Range ??)      <H(25B)

Author response: These H18B to C25B are part of the disordered/flipped thienyl rings. They are connected to their disordered carbon counterparts by 0.93 \%A just like the hydrogens on carbons in the main fragment.

 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.38
         From the CIF: _reflns_number_total               4511
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         4947
         Completeness (_total/calc)             91.19%
          Alert C: < 95% complete

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.38
         From the CIF: _reflns_number_total               4511
         From the CIF: _diffrn_reflns_limit_ max hkl   26.   13.   11.
         From the CIF: _diffrn_reflns_limit_ min hkl  -26.  -13.  -11.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   28.   14.   11.
         Calculated minimum hkl  -28.  -14.  -11.
          ALERT: Expected hkl max differ from CIF values


 6 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

Since the molecular volumes of thiophene and benzene are nearly identical, guest molecules that contain 2- or 3-thienyl rings are ideal probes for investigating the host–guest interactions during crystal growth of analogous phenyl-containing host species (Vaida et al., 1988). Thienyl-based guests have shown preferential inclusion into the host by keeping thienyl-ring S atoms pointed away from the face of growing crystals, possibly to avoid unfavorable electrostatic interactions between sulfur lone pairs coplanar with the thiophene ring and molecules already incorporated into the growing crystal face (Shimon et al., 1993). Research in our laboratories has centered on the synthesis of new 2- and 3-thienyl analogs to dope into phenyl-based hosts (Crundwell et al., 2003). Crystal structures of thienyl-containing molecules have shown that unsubstituted, terminal 2- and 3-thienyl rings often show ring flip disorder (Crundwell et al., 2002; 2003). These types of thienyl ring flip disorders are common; occurring in about one third of Cambridge Structural Database (Allen, 2002) entries containing terminal unsubstituted thienyl rings (Crundwell et al., 2002).

Initally, least-squares refinements on (I) were carried out using a simple model. The model contained four disordered atoms, S1B, C21B, S2B, and C25B, to account for disorder on each flipped thienyl ring. The following restraints were applied: (i) the positions of S1 and C21B, C21 and S1B, S2 and C25B, and C25 and S2B were equivalent. (ii) The anisotropic displacement parameters of S1 and S1B, C21 and C21B, S2 and S2B, and C25 and C25B were equivalent. (iii) The percent of thienyl ring flip was determined by refining a single occupancy variable for atoms S1, C21, S2, and C25 and their flipped analogs S1B, C21B, S2B, and C25B.

The resulting model had a 19.5 (3)% ring-flip disorder which lead to unrealistic S—C bond lengths [e.g. S1—C18 and S1—C25 bond lengths of 1.6492 (17) Å and 1.731 (3) Å, respectively]. The model had 255 parameters for 4511 observed reflections utilizing four restraints, and the refinement converged to an R = 0.0591 and Rw = 0.1336. (The CIF for this refinement as well as a scattering factor file are available as supplementary materials.)

The disorder model presented in this paper has two complete flipped thienyl rings (additional atoms S1B and C18B—C21B and S2B and C22B—C25B) and the following restraints were applied: (i) the positions for three of the four C atoms in each flipped thienyl ring were equivalent (e.g. C18 and C20B, C19 and C19B, C20 and C18B, C22 and C24B, C23 and C23B, and C24 and C22B). (ii) The anisotropic displacement parameters of S1 and S1B, C21 and C21B, S2 and S2B, and C25 and C25B were equivalent. (iii) Distances for every S—C bond were restrained to 1.710 (2) Å. (iv) A single occupancy variable was refined for both flipped rings.

Athough subjected to restraint, this model retained ideal S—C thienyl-ring bond lengths. The percent occupancy of the ring disorder refined to 18.89 (19)%. The total number of parameters in this model was 267 for 4511 observed reflections with 68 restraints. This refinement converged to an R = 0.0523 and Rw = 0.1182.

In 1965, Hamilton published a paper concerning significance tests on crystallographic R factors that provided crystallographers with equations for testing whether or not the addition of parameters during refinements significantly added to the model (Hamilton, 1965). The application of Hamilton's test to our refinements indicated that there was a significant reduction in the R value upon increasing the parameters even at the strictest level (0.005) of the statistical test. The choice to increase the number of parameters also lead to a more meaningful and physically significant structure solution since the simplified disorder model masked overlapping thienyl fragments to give unrealistic S—C bond lengths. With the increased use of crystallographic databases to extract bond lengths and angles, the need to fully access disorder models for reasonable structural features is ever important.

S2. Experimental

The title compound, (I), is a 3-thienyl derivative of tetraphenylcyclopentadienone. It can be prepared in adequate yields by reacting equamolar amounts of 3,3'-thenil and 1,3-diphenyl-2-propanone in absolute ethanol and potassium hydroxide in an identical manner to that used for the synthesis of tetraphenylcyclopentadienone (Pavia et al., 1998). The yield for the above reaction is 38%. Low yields of 32% were reported for the analogous dithien-2-yl species using this reaction scheme (Oda et al., 1994). Recrystallization from a warmed 50/50 mixture of ethanol and toluene afforded flat, deep purple needles (m.p. 454 K). [¹H NMR (CDCl₃, δ): 7.260 (m, 10H), 7.195 (dd, 2H), 6.842 (d, 2H), 6.705 (d, 2H); analysis, found: C 75.57, H 3.93%; calculated for C₂₅H₁₆OS₂: C 75.72, H 4.07%.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT and SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of (I) (Farrugia, 1997). Displacement ellipsoids are drawn at the 50% probability level. The ring flip disorder on each thienyl ring has been omitted for clarity.
	Fig. 2. Molecules of (I) exhibit an 18.89% thienyl ring flip disorder (Spek, 1990). Dashed lines show the minor ring component and H atoms have been removed for clarity.

1,4-diphenyl-2,3-dithien-3-ylcyclopentadien-1-one

Crystal data

C25H16OS2	F(000) = 824
Mr = 396.50	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Melting point: 454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 21.2902 (19) Å	Cell parameters from 17631 reflections
b = 10.4773 (9) Å	θ = 2.4–28.5°
c = 8.8835 (8) Å	µ = 0.28 mm^−1
β = 94.325 (3)°	T = 293 K
V = 1975.9 (3) Å^3	Plate, purple
Z = 4	0.4 × 0.35 × 0.25 mm

Data collection

Bruker SMART P3/512CCD diffractometer	4511 independent reflections
Radiation source: fine-focus sealed tube	3274 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 28.4°, θmin = 1.0°
Absorption correction: multi-scan SADABS; Shekdrick, 1996	h = −26→26
Tmin = 0.891, Tmax = 0.932	k = −13→13
17124 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 1.0401P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.004
4511 reflections	Δρmax = 0.32 e Å^−3
267 parameters	Δρmin = −0.48 e Å^−3
68 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0098 (11)

Special details

Experimental. For crystals of (I), intensities of reflections at high angles declined rapidly possible due to the observed disorder.

All hydrogen atoms were included in calculated positions with a C—H distance of 0.93 Å and were included in the refinement in riding motion approximation with U_iso = 1.2U_eq of the carrier atom.

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. Atoms pairs S1 & C21 and S2 & C25 are flip disordered over two positions; however, the refinement model contains complete disordered rings. To maintain ideal thienyl ring geometries, the disorder atoms in both thienyl rings are restained. (See Comment Section for details.) The percent of thienyl-ring flip disorder, refined as one variable for both rings, is 18.89%.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.19139 (8)	−0.07653 (15)	0.4913 (2)	0.0504 (4)
C1	0.21176 (10)	0.0317 (2)	0.4911 (2)	0.0380 (5)
C2	0.17404 (10)	0.1530 (2)	0.4633 (2)	0.0368 (5)
C3	0.21497 (10)	0.2515 (2)	0.4825 (2)	0.0353 (5)
C4	0.28199 (9)	0.19964 (19)	0.5138 (2)	0.0350 (5)
C5	0.27998 (10)	0.0709 (2)	0.5212 (2)	0.0378 (5)
C6	0.33077 (10)	−0.0251 (2)	0.5450 (3)	0.0400 (5)
C7	0.32373 (12)	−0.1265 (2)	0.6436 (3)	0.0515 (6)
H7A	0.2869	−0.1342	0.6927	0.062*
C8	0.37151 (15)	−0.2165 (3)	0.6693 (4)	0.0684 (9)
H8A	0.3664	−0.2839	0.7355	0.082*
C9	0.42635 (14)	−0.2063 (3)	0.5971 (4)	0.0735 (10)
H9A	0.4584	−0.2659	0.6156	0.088*
C10	0.43378 (13)	−0.1069 (3)	0.4968 (4)	0.0679 (9)
H10A	0.4705	−0.1006	0.4469	0.082*
C11	0.38640 (11)	−0.0170 (2)	0.4710 (3)	0.0515 (6)
H11A	0.3916	0.0494	0.4036	0.062*
C12	0.10449 (10)	0.1517 (2)	0.4354 (2)	0.0398 (5)
C13	0.07495 (11)	0.0592 (2)	0.3407 (3)	0.0474 (6)
H13A	0.0991	−0.0018	0.2953	0.057*
C14	0.00954 (12)	0.0580 (3)	0.3142 (3)	0.0591 (7)
H14A	−0.0097	−0.0032	0.2505	0.071*
C15	−0.02681 (12)	0.1472 (3)	0.3818 (3)	0.0625 (8)
H15A	−0.0704	0.1459	0.3640	0.075*
C16	0.00176 (12)	0.2384 (3)	0.4760 (3)	0.0608 (7)
H16A	−0.0228	0.2985	0.5216	0.073*
C17	0.06693 (11)	0.2409 (2)	0.5033 (3)	0.0492 (6)
H17A	0.0857	0.3025	0.5673	0.059*
S1	0.16123 (6)	0.61343 (7)	0.40144 (13)	0.0540 (3)	0.8111 (19)
C18	0.16631 (11)	0.45343 (15)	0.3682 (3)	0.0461 (6)	0.8111 (19)
H18A	0.1474	0.4136	0.2828	0.055*	0.8111 (19)
C19	0.20124 (9)	0.38945 (19)	0.4810 (2)	0.0357 (5)	0.8111 (19)
C20	0.22383 (11)	0.4730 (2)	0.5987 (3)	0.0434 (5)	0.8111 (19)
H20A	0.2482	0.4471	0.6846	0.052*	0.8111 (19)
C21	0.2055 (2)	0.5954 (3)	0.5705 (3)	0.0492 (8)	0.8111 (19)
H21A	0.2158	0.6627	0.6360	0.059*	0.8111 (19)
S2	0.41531 (4)	0.46536 (10)	0.48011 (12)	0.0486 (2)	0.8111 (19)
C22	0.34337 (8)	0.3942 (2)	0.4431 (3)	0.0436 (5)	0.8111 (19)
H22A	0.3118	0.4259	0.3752	0.052*	0.8111 (19)
C23	0.33786 (10)	0.28354 (19)	0.5268 (2)	0.0362 (5)	0.8111 (19)
C24	0.39375 (10)	0.2611 (2)	0.6215 (3)	0.0443 (5)	0.8111 (19)
H24A	0.3982	0.1931	0.6887	0.053*	0.8111 (19)
C25	0.43851 (17)	0.3454 (2)	0.6052 (4)	0.0521 (8)	0.8111 (19)
H25A	0.4783	0.3408	0.6556	0.063*	0.8111 (19)
S1B	0.2010 (3)	0.6277 (3)	0.5772 (7)	0.0540 (3)	0.19
C18B	0.22383 (11)	0.4730 (2)	0.5987 (3)	0.0434 (5)	0.19
H18B	0.2494	0.4450	0.6818	0.052*	0.1889 (19)
C19B	0.20124 (9)	0.38945 (19)	0.4810 (2)	0.0357 (5)	0.19
C20B	0.16631 (11)	0.45343 (15)	0.3682 (3)	0.0461 (6)	0.19
H20B	0.1489	0.4177	0.2787	0.055*	0.1889 (19)
C21B	0.1613 (11)	0.5818 (13)	0.4112 (16)	0.0492 (8)	0.19
H21B	0.1374	0.6396	0.3517	0.059*	0.1889 (19)
S2B	0.44271 (19)	0.3893 (3)	0.6056 (6)	0.0486 (2)	0.19
C22B	0.39375 (10)	0.2611 (2)	0.6215 (3)	0.0443 (5)	0.19
H22B	0.4022	0.1894	0.6814	0.053*	0.1889 (19)
C23B	0.33786 (10)	0.28354 (19)	0.5268 (2)	0.0362 (5)	0.19
C24B	0.34337 (8)	0.3942 (2)	0.4431 (3)	0.0436 (5)	0.19
H24B	0.3103	0.4224	0.3770	0.052*	0.1889 (19)
C25B	0.3982 (7)	0.4599 (17)	0.4604 (19)	0.0521 (8)	0.19
H25B	0.4095	0.5300	0.4041	0.063*	0.1889 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0488 (10)	0.0346 (8)	0.0670 (11)	−0.0088 (7)	−0.0015 (8)	0.0021 (8)
C1	0.0400 (11)	0.0339 (11)	0.0399 (12)	−0.0046 (9)	0.0017 (9)	−0.0013 (9)
C2	0.0381 (11)	0.0338 (11)	0.0384 (11)	−0.0030 (9)	0.0022 (9)	0.0007 (9)
C3	0.0360 (11)	0.0347 (11)	0.0352 (11)	−0.0002 (9)	0.0029 (8)	0.0016 (9)
C4	0.0336 (10)	0.0336 (10)	0.0377 (11)	−0.0020 (8)	0.0034 (8)	−0.0006 (9)
C5	0.0355 (11)	0.0341 (11)	0.0436 (12)	−0.0018 (9)	0.0023 (9)	−0.0003 (9)
C6	0.0381 (11)	0.0305 (10)	0.0502 (13)	−0.0011 (9)	−0.0046 (9)	−0.0058 (9)
C7	0.0564 (15)	0.0351 (12)	0.0610 (15)	−0.0024 (11)	−0.0078 (12)	0.0027 (11)
C8	0.077 (2)	0.0385 (14)	0.085 (2)	0.0074 (13)	−0.0263 (17)	0.0009 (14)
C9	0.0587 (18)	0.0442 (15)	0.112 (3)	0.0152 (13)	−0.0327 (17)	−0.0236 (16)
C10	0.0441 (14)	0.0561 (17)	0.103 (2)	0.0049 (12)	−0.0007 (14)	−0.0321 (17)
C11	0.0459 (13)	0.0412 (12)	0.0675 (17)	0.0009 (11)	0.0053 (12)	−0.0112 (12)
C12	0.0370 (11)	0.0411 (12)	0.0412 (12)	−0.0056 (9)	0.0014 (9)	0.0039 (10)
C13	0.0459 (13)	0.0479 (13)	0.0478 (13)	−0.0082 (11)	−0.0007 (10)	0.0006 (11)
C14	0.0496 (15)	0.0709 (18)	0.0551 (15)	−0.0164 (13)	−0.0075 (12)	0.0045 (14)
C15	0.0334 (12)	0.092 (2)	0.0606 (16)	−0.0064 (13)	−0.0034 (11)	0.0094 (15)
C16	0.0397 (13)	0.0797 (19)	0.0637 (17)	0.0055 (13)	0.0083 (12)	0.0021 (15)
C17	0.0410 (12)	0.0553 (14)	0.0516 (14)	−0.0026 (11)	0.0051 (10)	−0.0037 (11)
S1	0.0545 (5)	0.0346 (5)	0.0718 (6)	0.0100 (5)	−0.0031 (4)	0.0044 (4)
C18	0.0456 (13)	0.0409 (12)	0.0503 (13)	0.0021 (10)	−0.0053 (10)	0.0007 (10)
C19	0.0321 (10)	0.0336 (11)	0.0418 (12)	−0.0013 (8)	0.0050 (8)	0.0004 (9)
C20	0.0423 (12)	0.0421 (12)	0.0454 (12)	−0.0009 (10)	0.0002 (10)	−0.0040 (10)
C21	0.0515 (19)	0.0240 (16)	0.072 (2)	0.0088 (16)	0.0063 (15)	−0.0087 (16)
S2	0.0414 (5)	0.0357 (4)	0.0698 (6)	−0.0122 (4)	0.0109 (4)	−0.0010 (4)
C22	0.0399 (12)	0.0363 (12)	0.0550 (14)	−0.0038 (9)	0.0067 (10)	0.0021 (10)
C23	0.0360 (11)	0.0310 (10)	0.0419 (11)	−0.0012 (8)	0.0054 (9)	−0.0028 (9)
C24	0.0394 (12)	0.0440 (12)	0.0492 (13)	−0.0047 (10)	0.0018 (10)	0.0013 (10)
C25	0.0516 (18)	0.0319 (16)	0.071 (2)	−0.0096 (15)	−0.0043 (15)	−0.0064 (17)
S1B	0.0545 (5)	0.0346 (5)	0.0718 (6)	0.0100 (5)	−0.0031 (4)	0.0044 (4)
C18B	0.0423 (12)	0.0421 (12)	0.0454 (12)	−0.0009 (10)	0.0002 (10)	−0.0040 (10)
C19B	0.0321 (10)	0.0336 (11)	0.0418 (12)	−0.0013 (8)	0.0050 (8)	0.0004 (9)
C20B	0.0456 (13)	0.0409 (12)	0.0503 (13)	0.0021 (10)	−0.0053 (10)	0.0007 (10)
C21B	0.0515 (19)	0.0240 (16)	0.072 (2)	0.0088 (16)	0.0063 (15)	−0.0087 (16)
S2B	0.0414 (5)	0.0357 (4)	0.0698 (6)	−0.0122 (4)	0.0109 (4)	−0.0010 (4)
C22B	0.0394 (12)	0.0440 (12)	0.0492 (13)	−0.0047 (10)	0.0018 (10)	0.0013 (10)
C23B	0.0360 (11)	0.0310 (10)	0.0419 (11)	−0.0012 (8)	0.0054 (9)	−0.0028 (9)
C24B	0.0399 (12)	0.0363 (12)	0.0550 (14)	−0.0038 (9)	0.0067 (10)	0.0021 (10)
C25B	0.0516 (18)	0.0319 (16)	0.071 (2)	−0.0096 (15)	−0.0043 (15)	−0.0064 (17)

Geometric parameters (Å, º)

O1—C1	1.214 (3)	C14—H14A	0.9300
C1—C2	1.513 (3)	C15—C16	1.381 (4)
C1—C5	1.514 (3)	C15—H15A	0.9300
C2—C3	1.353 (3)	C16—C17	1.391 (3)
C2—C12	1.483 (3)	C16—H16A	0.9300
C3—C19	1.474 (3)	C17—H17A	0.9300
C3—C4	1.533 (3)	S1—C18	1.7071 (16)
C4—C5	1.351 (3)	S1—C21	1.7225 (19)
C4—C23	1.477 (3)	C18—C19	1.377 (3)
C5—C6	1.480 (3)	C18—H18A	0.9300
C6—C7	1.392 (3)	C19—C20	1.420 (3)
C6—C11	1.400 (3)	C20—C21	1.358 (3)
C7—C8	1.393 (4)	C20—H20A	0.9300
C7—H7A	0.9300	C21—H21A	0.9300
C8—C9	1.378 (5)	S2—C22	1.7130 (16)
C8—H8A	0.9300	S2—C25	1.7254 (18)
C9—C10	1.387 (5)	C22—C23	1.387 (3)
C9—H9A	0.9300	C22—H22A	0.9300
C10—C11	1.387 (4)	C23—C24	1.424 (3)
C10—H10A	0.9300	C24—C25	1.315 (4)
C11—H11A	0.9300	C24—H24A	0.9300
C12—C17	1.397 (3)	C25—H25A	0.9300
C12—C13	1.401 (3)	S1B—C21B	1.712 (2)
C13—C14	1.395 (3)	C21B—H21B	0.9300
C13—H13A	0.9300	S2B—C25B	1.710 (2)
C14—C15	1.379 (4)	C25B—H25B	0.9300
O1—C1—C2	126.8 (2)	C15—C14—H14A	119.8
O1—C1—C5	126.2 (2)	C13—C14—H14A	119.8
C2—C1—C5	106.95 (17)	C14—C15—C16	119.8 (2)
C3—C2—C12	130.8 (2)	C14—C15—H15A	120.1
C3—C2—C1	106.94 (18)	C16—C15—H15A	120.1
C12—C2—C1	122.05 (18)	C15—C16—C17	120.5 (3)
C2—C3—C19	128.41 (19)	C15—C16—H16A	119.8
C2—C3—C4	109.51 (18)	C17—C16—H16A	119.8
C19—C3—C4	122.04 (18)	C16—C17—C12	120.5 (2)
C5—C4—C23	128.22 (19)	C16—C17—H17A	119.7
C5—C4—C3	109.30 (18)	C12—C17—H17A	119.7
C23—C4—C3	122.45 (18)	C18—S1—C21	90.31 (13)
C4—C5—C6	131.3 (2)	C19—C18—S1	112.95 (16)
C4—C5—C1	107.18 (18)	C19—C18—H18A	123.5
C6—C5—C1	121.46 (18)	S1—C18—H18A	123.5
C7—C6—C11	118.5 (2)	C18—C19—C20	111.75 (18)
C7—C6—C5	119.8 (2)	C18—C19—C3	125.41 (18)
C11—C6—C5	121.7 (2)	C20—C19—C3	122.84 (19)
C6—C7—C8	120.5 (3)	C21—C20—C19	111.7 (2)
C6—C7—H7A	119.7	C21—C20—H20A	124.2
C8—C7—H7A	119.7	C19—C20—H20A	124.2
C9—C8—C7	120.3 (3)	C20—C21—S1	113.29 (19)
C9—C8—H8A	119.9	C20—C21—H21A	123.4
C7—C8—H8A	119.9	S1—C21—H21A	123.4
C8—C9—C10	120.0 (3)	C22—S2—C25	90.83 (15)
C8—C9—H9A	120.0	C23—C22—S2	111.82 (16)
C10—C9—H9A	120.0	C23—C22—H22A	124.1
C9—C10—C11	120.0 (3)	S2—C22—H22A	124.1
C9—C10—H10A	120.0	C22—C23—C24	110.74 (18)
C11—C10—H10A	120.0	C22—C23—C4	123.75 (18)
C10—C11—C6	120.8 (3)	C24—C23—C4	125.49 (18)
C10—C11—H11A	119.6	C25—C24—C23	113.9 (2)
C6—C11—H11A	119.6	C25—C24—H24A	123.1
C17—C12—C13	118.5 (2)	C23—C24—H24A	123.1
C17—C12—C2	121.2 (2)	C24—C25—S2	112.7 (2)
C13—C12—C2	120.3 (2)	C24—C25—H25A	123.7
C14—C13—C12	120.3 (2)	S2—C25—H25A	123.7
C14—C13—H13A	119.9	S1B—C21B—H21B	121.3
C12—C13—H13A	119.9	S2B—C25B—H25B	126.6
C15—C14—C13	120.5 (3)