Crystallographic and molecular mechanics investigation of an order–disorder transition and dimorphism in 5H,10H-dithiolo[2,3-b]-2,5-benzodithiocine-2-thione

Single-crystal X-ray structures are presented for three forms of 5H,10H-dithiolo[2,3-b]-2,5-benzodithiocine-2-thione. The α (at 150 K) and α′ (at ambient) forms are very similar and differ only in the presence of crystallographic m symmetry in the molecules of α′, which is absent in the case of α. This pair is related by an order–disorder transition. The β phase (also determined at 150 K) has a different structure in terms of the molecular packing from either of the other two and therefore constitutes a true polymorph. Molecular mechanics calculations indicated that the most stable CHCl₃-solvated conformations for the title compound were a pair of twisted U-shaped enantiomers, U_R and U_L, i.e. similar to the arrangements found in the α and β phases, with the low-lying saddle point between them corresponding to the situation in the α′ phase. These calculations also indicated that the most stable CHCl₃-solvated conformation for the related dibromo-5H,10H-dithiolo[2,3-b]-2,5-benzodithiocine-2-thione was Z-shaped, in agreement with the crystal structure determined earlier for its DMSO solvate [Wang et al. (1998). Synthesis, pp. 1615–1618].

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997), COLLECT (Hooft, 1998) for alpha-2, beta-2; Nicolet P3 software (Nicolet, 1980) for alphaprime-2. Cell refinement: DENZO, COLLECT for alpha-2, beta-2; Nicolet P3 software (Nicolet, 1980) for alphaprime-2. Data reduction: DENZO, COLLECT for alpha-2, beta-2; RDNIC (Howie, 1980) for alphaprime-2. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 19970 for alpha-2; ORTEX (McArdle, 1994) for alphaprime-2, beta-2. For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(alpha-2) 5H, 10H-dithiolo[2,3-b][2,5]benzodithiocine-2-thione [low temperature (150 K) P monoclinic form]

Crystal data

C11H8S5	F(000) = 616
Mr = 300.47	Dx = 1.617 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 21934 reflections
a = 11.9290 (2) Å	θ = 2.3–27.5°
b = 11.7639 (2) Å	µ = 0.91 mm^−1
c = 9.0612 (2) Å	T = 150 K
β = 103.9498 (10)°	Block, red
V = 1234.07 (4) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Enraf Nonius KappaCCD area detector diffractometer	2825 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2500 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −15→15
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −15→15
Tmin = 0.728, Tmax = 0.835	l = −11→11
21934 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.05	Calculated w = 1/[σ^2(Fo^2) + (0.037P)^2 + 0.4749P] where P = (Fo^2 + 2Fc^2)/3
2825 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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.

H placed in calculated positions and refined with a riding model.

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

	x	y	z	Uiso*/Ueq
S1	0.87835 (4)	0.54914 (4)	0.84600 (4)	0.03210 (12)
S2	0.85623 (3)	0.64034 (3)	0.53120 (4)	0.02204 (11)
S3	0.84961 (3)	0.62066 (4)	0.19853 (4)	0.02360 (11)
S4	0.83794 (3)	0.39943 (3)	0.57473 (4)	0.02268 (11)
S5	0.82017 (3)	0.33413 (3)	0.25468 (5)	0.02480 (11)
C1	0.85892 (12)	0.53227 (14)	0.66189 (17)	0.0220 (3)
C2	0.84468 (12)	0.55589 (13)	0.36993 (16)	0.0180 (3)
C3	0.69534 (13)	0.64069 (13)	0.10425 (18)	0.0237 (3)
H3A	0.6756	0.7219	0.1114	0.028*
H3B	0.6836	0.6220	−0.0049	0.028*
C4	0.61356 (12)	0.57030 (13)	0.16900 (16)	0.0187 (3)
C5	0.53441 (13)	0.62641 (14)	0.23388 (18)	0.0241 (3)
H5	0.5342	0.7071	0.2362	0.029*
C6	0.45613 (13)	0.56720 (15)	0.2950 (2)	0.0293 (4)
H6	0.4031	0.6070	0.3392	0.035*
C7	0.83572 (12)	0.44249 (13)	0.38986 (16)	0.0182 (3)
C8	0.69827 (13)	0.38524 (14)	0.10249 (17)	0.0227 (3)
H8A	0.7283	0.4342	0.0318	0.027*
H8B	0.6590	0.3194	0.0441	0.027*
C9	0.61277 (12)	0.45108 (13)	0.16521 (16)	0.0184 (3)
C10	0.53292 (12)	0.39238 (13)	0.22565 (17)	0.0224 (3)
H10	0.5315	0.3117	0.2217	0.027*
C11	0.45562 (13)	0.44895 (15)	0.29134 (19)	0.0272 (4)
H11	0.4026	0.4074	0.3336	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0337 (2)	0.0465 (3)	0.0158 (2)	0.00308 (19)	0.00529 (16)	−0.00005 (17)
S2	0.0263 (2)	0.0205 (2)	0.01767 (19)	0.00004 (15)	0.00196 (15)	−0.00267 (14)
S3	0.02189 (19)	0.0296 (2)	0.0187 (2)	−0.00717 (15)	0.00363 (15)	0.00461 (15)
S4	0.0239 (2)	0.0225 (2)	0.0209 (2)	0.00112 (15)	0.00373 (15)	0.00565 (15)
S5	0.0241 (2)	0.0208 (2)	0.0270 (2)	0.00640 (15)	0.00149 (16)	−0.00574 (16)
C1	0.0166 (7)	0.0298 (8)	0.0189 (7)	0.0030 (6)	0.0029 (6)	0.0012 (6)
C2	0.0162 (7)	0.0213 (7)	0.0158 (7)	−0.0003 (5)	0.0025 (5)	−0.0006 (5)
C3	0.0249 (8)	0.0223 (8)	0.0217 (8)	−0.0006 (6)	0.0009 (6)	0.0056 (6)
C4	0.0169 (7)	0.0193 (7)	0.0165 (7)	−0.0006 (6)	−0.0027 (5)	−0.0002 (6)
C5	0.0203 (7)	0.0195 (7)	0.0295 (8)	0.0018 (6)	−0.0003 (6)	−0.0045 (6)
C6	0.0202 (7)	0.0336 (9)	0.0344 (9)	0.0026 (7)	0.0072 (7)	−0.0072 (7)
C7	0.0156 (6)	0.0210 (7)	0.0173 (7)	0.0014 (5)	0.0025 (5)	−0.0009 (6)
C8	0.0242 (7)	0.0227 (8)	0.0189 (7)	0.0013 (6)	0.0009 (6)	−0.0038 (6)
C9	0.0178 (7)	0.0187 (7)	0.0155 (7)	0.0004 (5)	−0.0022 (5)	−0.0017 (5)
C10	0.0203 (7)	0.0194 (8)	0.0237 (8)	−0.0030 (6)	−0.0020 (6)	0.0003 (6)
C11	0.0193 (7)	0.0323 (9)	0.0295 (9)	−0.0050 (6)	0.0047 (6)	0.0021 (7)

Geometric parameters (Å, º)

S1—C1	1.6400 (15)	C2—C7	1.354 (2)
S2—C1	1.7324 (16)	C3—C4	1.502 (2)
S2—C2	1.7449 (15)	C4—C5	1.393 (2)
S3—C2	1.7436 (14)	C4—C9	1.403 (2)
S3—C3	1.8477 (16)	C5—C6	1.383 (2)
S4—C1	1.7416 (17)	C6—C11	1.391 (3)
S4—C7	1.7442 (15)	C8—C9	1.498 (2)
S5—C7	1.7466 (15)	C9—C10	1.391 (2)
S5—C8	1.8468 (16)	C10—C11	1.383 (2)
C1—S2—C2	98.01 (7)	C9—C4—C3	122.86 (13)
C2—S3—C3	102.93 (7)	C6—C5—C4	121.47 (15)
C1—S4—C7	98.17 (7)	C5—C6—C11	119.57 (15)
C7—S5—C8	102.55 (7)	C2—C7—S4	115.53 (11)
S1—C1—S2	125.54 (10)	C2—C7—S5	128.61 (12)
S1—C1—S4	122.65 (10)	S4—C7—S5	115.85 (9)
S2—C1—S4	111.81 (8)	C9—C8—S5	111.76 (10)
C7—C2—S3	124.76 (12)	C10—C9—C4	119.20 (13)
C7—C2—S2	116.24 (11)	C10—C9—C8	119.10 (14)
S3—C2—S2	118.97 (9)	C4—C9—C8	121.67 (13)
C4—C3—S3	114.66 (10)	C11—C10—C9	121.43 (15)
C5—C4—C9	118.86 (14)	C10—C11—C6	119.46 (15)
C5—C4—C3	118.27 (14)
C2—S2—C1—S1	175.33 (10)	S2—C2—C7—S5	178.67 (8)
C2—S2—C1—S4	−4.76 (9)	C1—S4—C7—C2	−2.70 (13)
C7—S4—C1—S1	−175.44 (9)	C1—S4—C7—S5	178.19 (8)
C7—S4—C1—S2	4.65 (9)	C8—S5—C7—C2	−50.73 (15)
C3—S3—C2—C7	86.98 (14)	C8—S5—C7—S4	128.25 (9)
C3—S3—C2—S2	−95.04 (9)	C7—S5—C8—C9	−33.34 (13)
C1—S2—C2—C7	3.16 (13)	C5—C4—C9—C10	0.2 (2)
C1—S2—C2—S3	−174.99 (9)	C3—C4—C9—C10	−178.99 (13)
C2—S3—C3—C4	−17.10 (13)	C5—C4—C9—C8	−177.68 (13)
S3—C3—C4—C5	117.42 (14)	C3—C4—C9—C8	3.1 (2)
S3—C3—C4—C9	−63.35 (17)	S5—C8—C9—C10	−79.69 (15)
C9—C4—C5—C6	0.4 (2)	S5—C8—C9—C4	98.22 (15)
C3—C4—C5—C6	179.67 (14)	C4—C9—C10—C11	−1.0 (2)
C4—C5—C6—C11	−0.3 (2)	C8—C9—C10—C11	176.97 (14)
S3—C2—C7—S4	177.72 (8)	C9—C10—C11—C6	1.1 (2)
S2—C2—C7—S4	−0.31 (16)	C5—C6—C11—C10	−0.5 (2)
S3—C2—C7—S5	−3.3 (2)

(alphaprime-2) 5H,10H-Dithiolo[2,3-b][2,5]benzodithiocine-2-thione (C-centred monoclinic form)

Crystal data

C11H8S5	F(000) = 616
Mr = 300.47	Dx = 1.582 Mg m^−3
Monoclinic, C2/m	Melting point: 479 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 12.075 (8) Å	Cell parameters from 14 reflections
b = 11.825 (8) Å	θ = 10.8–12.9°
c = 9.063 (6) Å	µ = 0.89 mm^−1
β = 102.80 (5)°	T = 298 K
V = 1261.9 (15) Å^3	Block, pale brown
Z = 4	0.60 × 0.46 × 0.40 mm

Data collection

Nicolet P3 diffractometer	1166 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 30.1°, θmin = 2.3°
θ–2θ scans	h = −16→16
Absorption correction: ψ ?	k = −16→0
Tmin = 0.619, Tmax = 0.719	l = 0→12
2034 measured reflections	2 standard reflections every 50 reflections
1932 independent reflections	intensity decay: 0.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.215	Only H-atom displacement parameters refined
S = 1.05	Calculated w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 8.1837P] where P = (Fo^2 + 2Fc^2)/3
1932 reflections	(Δ/σ)max < 0.001
78 parameters	Δρmax = 0.92 e Å^−3
0 restraints	Δρmin = −0.95 e Å^−3

Special details

Experimental. Variable scan rates, dependent upon pre-scan intensity (Ip), were in the range 5.33 (Ip<150) to 58.6 (Ip>2500) degrees 2θ per min. Scan widths, dependent upon 2θ were in the range 2.4 to 2.8 degrees 2θ. The total background count time (on either side of the peak) and the scan time were set equal.

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.

All non-H aniso. H in calculated positions refined with a riding model with separate group U_iso for methylene and aryl H.

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

	x	y	z	Uiso*/Ueq
S1	0.3778 (2)	0.0000	0.3365 (3)	0.147 (2)
S2	0.34509 (12)	0.12081 (14)	0.04410 (17)	0.0728 (5)
S3	0.32964 (15)	0.1438 (2)	−0.2844 (2)	0.1171 (10)
C1	0.3580 (6)	0.0000	0.1521 (8)	0.076 (3)
C2	0.3363 (3)	0.0564 (4)	−0.1288 (5)	0.0438 (10)
C3	0.1916 (4)	0.1264 (5)	−0.3999 (6)	0.0654 (15)
H3A	0.1592	0.2008	−0.4259	0.12 (2)*
H3B	0.1987	0.0901	−0.4933	0.12 (2)*
C4	0.1097 (3)	0.0589 (4)	−0.3320 (5)	0.0430 (10)
C5	0.0330 (4)	0.1159 (4)	−0.2676 (6)	0.0541 (12)
H5	0.0330	0.1946	−0.2675	0.074 (13)*
C6	−0.0439 (4)	0.0585 (5)	−0.2031 (6)	0.0669 (15)
H6	−0.0953	0.0982	−0.1600	0.074 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0658 (15)	0.340 (6)	0.0355 (10)	0.000	0.0101 (10)	0.000
S2	0.0597 (8)	0.0762 (10)	0.0714 (9)	0.0100 (7)	−0.0094 (6)	−0.0334 (8)
S3	0.0766 (11)	0.148 (2)	0.1040 (14)	−0.0657 (12)	−0.0280 (9)	0.0790 (14)
C1	0.030 (3)	0.153 (9)	0.043 (4)	0.000	0.002 (3)	0.000
C2	0.036 (2)	0.051 (2)	0.043 (2)	−0.0041 (18)	0.0052 (16)	0.006 (2)
C3	0.059 (3)	0.079 (4)	0.054 (3)	−0.013 (3)	0.003 (2)	0.018 (3)
C4	0.037 (2)	0.051 (2)	0.0369 (19)	0.0004 (18)	−0.0012 (16)	0.0057 (18)
C5	0.045 (2)	0.047 (3)	0.063 (3)	0.008 (2)	−0.002 (2)	−0.004 (2)
C6	0.043 (3)	0.087 (4)	0.069 (3)	0.011 (3)	0.010 (2)	−0.012 (3)

Geometric parameters (Å, º)

S1—C1	1.635 (8)	C2—C2^i	1.334 (9)
S2—C1	1.719 (4)	C3—C4	1.506 (7)
S2—C2	1.724 (5)	C4—C5	1.376 (6)
S3—C2	1.735 (5)	C4—C4^i	1.392 (9)
S3—C3	1.773 (5)	C5—C6	1.380 (7)
C1—S2^i	1.719 (4)	C6—C6^i	1.384 (12)
C1—S2—C2	97.5 (3)	S2—C2—S3	117.2 (3)
C2—S3—C3	106.2 (2)	C4—C3—S3	115.9 (3)
S1—C1—S2^i	123.8 (2)	C5—C4—C4^i	119.4 (3)
S1—C1—S2	123.8 (2)	C5—C4—C3	118.6 (5)
S2^i—C1—S2	112.4 (4)	C4^i—C4—C3	122.1 (3)
C2^i—C2—S2	116.20 (16)	C4—C5—C6	121.2 (5)
C2^i—C2—S3	126.55 (18)	C5—C6—C6^i	119.5 (3)
C2—S2—C1—S1	176.4 (4)	C4^i—C4—C5—C6	0.0 (5)
C2—S2—C1—S2^i	−4.8 (4)	C3—C4—C5—C6	−179.8 (4)
C1—S2—C2—C2^i	3.0 (3)	C4—C5—C6—C6^i	0.0 (5)
C1—S2—C2—S3	−176.4 (3)	S2—C2—C2^i—S2^i	0.0
C3—S3—C2—C2^i	68.6 (3)	S2—C2—C2^i—S3^i	−179.4 (3)
C3—S3—C2—S2	−112.1 (3)	C3—C4—C4^i—C3^i	0.0
C2—S3—C3—C4	8.7 (5)	C3—C4—C4^i—C5^i	179.7 (5)
S3—C3—C4—C5	98.5 (5)	C5—C6—C6^i—C5^i	0.0
S3—C3—C4—C4^i	−81.2 (4)

Symmetry code: (i) x, −y, z.

(beta-2) 5H,10H-Dithiolo[2,3-b][2,5]benzodithiocine-2-thione (P monoclinic form)

Crystal data

C11H8S5	F(000) = 1232
Mr = 300.47	Dx = 1.618 Mg m^−3
Monoclinic, P21/n	Melting point: 479 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.5683 (2) Å	Cell parameters from 31494 reflections
b = 16.2080 (4) Å	θ = 1.7–26.4°
c = 17.8980 (4) Å	µ = 0.91 mm^−1
β = 97.1103 (14)°	T = 150 K
V = 2466.47 (10) Å^3	Block, orange
Z = 8	0.20 × 0.10 × 0.10 mm

Data collection

Enraf Nonius KappaCCD area detector diffractometer	5044 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	3825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
Detector resolution: 9.091 pixels mm^-1	θmax = 26.4°, θmin = 1.7°
ω scans	h = −10→10
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −20→20
Tmin = 0.809, Tmax = 0.914	l = −22→22
31494 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.03	Calculated w = 1/[σ^2(Fo^2) + (0.0422P)^2 + 0.3638P] where P = (Fo^2 + 2Fc^2)/3
5044 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Sample crystal recrystallized from acetone.

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.

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

	x	y	z	Uiso*/Ueq
S1A	0.41703 (11)	0.31394 (5)	0.39816 (4)	0.0468 (2)
S2A	0.48290 (8)	0.38802 (4)	0.25226 (3)	0.02541 (16)
S3A	0.46775 (7)	0.39657 (4)	0.08388 (4)	0.02700 (16)
S4A	0.24084 (8)	0.26506 (4)	0.25101 (4)	0.03178 (18)
S5A	0.15965 (8)	0.25728 (4)	0.08623 (4)	0.03138 (18)
C1A	0.3854 (3)	0.32143 (15)	0.30606 (14)	0.0294 (6)
C2A	0.3926 (3)	0.35800 (14)	0.16329 (13)	0.0217 (5)
C3A	0.3343 (3)	0.48286 (15)	0.05067 (14)	0.0266 (6)
H3A1	0.3909	0.5354	0.0624	0.032*
H3A2	0.3109	0.4791	−0.0048	0.032*
C4A	0.1812 (3)	0.48626 (15)	0.08333 (13)	0.0225 (5)
C5A	0.1461 (3)	0.55690 (15)	0.12264 (14)	0.0275 (6)
H5A	0.2208	0.6004	0.1294	0.033*
C6A	0.0049 (3)	0.56489 (17)	0.15197 (15)	0.0335 (7)
H6A	−0.0174	0.6137	0.1781	0.040*
C7A	0.2779 (3)	0.30056 (15)	0.16268 (14)	0.0237 (6)
C8A	0.0960 (3)	0.34753 (15)	0.02830 (14)	0.0279 (6)
H8A1	0.1770	0.3600	−0.0050	0.033*
H8A2	−0.0024	0.3335	−0.0042	0.033*
C9A	0.0684 (3)	0.42316 (15)	0.07276 (13)	0.0226 (5)
C10A	−0.0715 (3)	0.43167 (16)	0.10326 (14)	0.0279 (6)
H10A	−0.1472	0.3886	0.0967	0.034*
C11A	−0.1033 (3)	0.50155 (18)	0.14299 (15)	0.0330 (6)
H11A	−0.1995	0.5059	0.1641	0.040*
S1B	0.59044 (10)	0.69235 (5)	0.10370 (4)	0.0388 (2)
S2B	0.73645 (8)	0.72871 (4)	0.26118 (4)	0.02855 (17)
S3B	0.76456 (8)	0.71429 (4)	0.42977 (4)	0.03245 (18)
S4B	0.52733 (7)	0.59062 (4)	0.23427 (3)	0.02455 (16)
S5B	0.52065 (7)	0.54543 (4)	0.39349 (4)	0.02760 (17)
C1B	0.6167 (3)	0.67286 (15)	0.19431 (14)	0.0251 (6)
C2B	0.6929 (3)	0.67593 (15)	0.34142 (13)	0.0232 (5)
C3B	0.9397 (3)	0.65037 (16)	0.45796 (15)	0.0339 (7)
H3B1	1.0344	0.6837	0.4524	0.041*
H3B2	0.9426	0.6366	0.5120	0.041*
C4B	0.9490 (3)	0.57132 (16)	0.41449 (14)	0.0259 (6)
C5B	1.0746 (3)	0.55999 (16)	0.37282 (15)	0.0304 (6)
H5B	1.1495	0.6029	0.3712	0.036*
C6B	1.0924 (3)	0.48764 (18)	0.33384 (15)	0.0342 (7)
H6B	1.1791	0.4812	0.3060	0.041*
C7B	0.5942 (3)	0.61072 (14)	0.32847 (13)	0.0207 (5)
C8B	0.6976 (3)	0.51571 (16)	0.45687 (14)	0.0288 (6)
H8B1	0.7192	0.5579	0.4968	0.035*
H8B2	0.6781	0.4626	0.4814	0.035*
C9B	0.8387 (3)	0.50722 (15)	0.41546 (13)	0.0237 (6)
C10B	0.8589 (3)	0.43479 (15)	0.37602 (14)	0.0271 (6)
H10B	0.7849	0.3913	0.3771	0.032*
C11B	0.9846 (3)	0.42494 (17)	0.33541 (15)	0.0341 (7)
H11B	0.9965	0.3752	0.3087	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0757 (6)	0.0385 (4)	0.0265 (4)	0.0075 (4)	0.0074 (4)	0.0102 (3)
S2A	0.0279 (4)	0.0234 (3)	0.0244 (3)	0.0015 (3)	0.0013 (3)	0.0022 (3)
S3A	0.0208 (4)	0.0347 (4)	0.0266 (3)	0.0020 (3)	0.0070 (3)	0.0057 (3)
S4A	0.0346 (4)	0.0254 (4)	0.0376 (4)	−0.0007 (3)	0.0132 (3)	0.0073 (3)
S5A	0.0285 (4)	0.0221 (3)	0.0419 (4)	−0.0027 (3)	−0.0018 (3)	−0.0029 (3)
C1A	0.0377 (16)	0.0214 (13)	0.0299 (14)	0.0094 (12)	0.0070 (12)	0.0065 (11)
C2A	0.0212 (14)	0.0199 (13)	0.0243 (13)	0.0034 (11)	0.0039 (10)	0.0028 (10)
C3A	0.0237 (14)	0.0279 (14)	0.0283 (14)	0.0003 (11)	0.0036 (11)	0.0082 (11)
C4A	0.0187 (13)	0.0243 (13)	0.0232 (13)	0.0025 (11)	−0.0026 (10)	0.0049 (10)
C5A	0.0258 (15)	0.0222 (14)	0.0321 (14)	−0.0011 (11)	−0.0061 (11)	0.0012 (11)
C6A	0.0346 (17)	0.0309 (16)	0.0337 (16)	0.0095 (13)	−0.0006 (12)	−0.0051 (12)
C7A	0.0196 (14)	0.0220 (13)	0.0296 (14)	0.0043 (11)	0.0038 (11)	0.0016 (10)
C8A	0.0262 (15)	0.0287 (14)	0.0278 (14)	−0.0008 (12)	−0.0010 (11)	−0.0010 (11)
C9A	0.0233 (14)	0.0226 (13)	0.0212 (13)	0.0013 (11)	−0.0002 (10)	0.0026 (10)
C10A	0.0205 (14)	0.0298 (15)	0.0326 (15)	0.0001 (12)	−0.0006 (11)	0.0050 (11)
C11A	0.0237 (15)	0.0408 (17)	0.0362 (16)	0.0089 (13)	0.0103 (12)	0.0014 (13)
S1B	0.0581 (5)	0.0357 (4)	0.0233 (4)	0.0034 (4)	0.0072 (3)	0.0058 (3)
S2B	0.0298 (4)	0.0235 (3)	0.0325 (4)	−0.0047 (3)	0.0045 (3)	0.0036 (3)
S3B	0.0376 (4)	0.0277 (4)	0.0299 (4)	0.0062 (3)	−0.0043 (3)	−0.0080 (3)
S4B	0.0262 (4)	0.0226 (3)	0.0242 (3)	−0.0014 (3)	0.0006 (3)	0.0021 (2)
S5B	0.0222 (4)	0.0331 (4)	0.0286 (4)	0.0007 (3)	0.0075 (3)	0.0078 (3)
C1B	0.0282 (15)	0.0230 (13)	0.0248 (13)	0.0062 (11)	0.0056 (11)	0.0036 (10)
C2B	0.0230 (14)	0.0230 (13)	0.0234 (13)	0.0059 (11)	0.0025 (10)	0.0000 (10)
C3B	0.0297 (16)	0.0327 (16)	0.0361 (16)	0.0041 (13)	−0.0084 (12)	−0.0074 (12)
C4B	0.0221 (14)	0.0286 (14)	0.0250 (13)	0.0059 (11)	−0.0045 (11)	−0.0001 (11)
C5B	0.0184 (14)	0.0303 (15)	0.0411 (16)	0.0004 (12)	−0.0017 (12)	0.0036 (12)
C6B	0.0207 (15)	0.0422 (17)	0.0405 (17)	0.0080 (13)	0.0067 (12)	0.0014 (13)
C7B	0.0178 (13)	0.0225 (13)	0.0221 (12)	0.0043 (10)	0.0037 (10)	0.0024 (10)
C8B	0.0298 (15)	0.0324 (15)	0.0242 (14)	0.0032 (12)	0.0033 (11)	0.0049 (11)
C9B	0.0203 (14)	0.0263 (14)	0.0232 (13)	0.0048 (11)	−0.0025 (10)	0.0057 (10)
C10B	0.0224 (14)	0.0232 (14)	0.0337 (15)	0.0017 (11)	−0.0040 (11)	0.0028 (11)
C11B	0.0298 (16)	0.0303 (15)	0.0409 (17)	0.0090 (13)	−0.0013 (13)	−0.0065 (12)

Geometric parameters (Å, º)

S1A—C1A	1.642 (3)	S1B—C1B	1.640 (2)
S2A—C1A	1.729 (3)	S2B—C1B	1.732 (3)
S2A—C2A	1.751 (2)	S2B—C2B	1.751 (2)
S2A—S4B	3.3259 (9)	S2B—S2A^ii	3.5568 (9)
S2A—S2B^i	3.5568 (9)	S3B—C2B	1.739 (2)
S3A—C2A	1.747 (2)	S3B—C3B	1.842 (3)
S3A—C3A	1.857 (2)	S4B—C1B	1.735 (3)
S4A—C1A	1.743 (3)	S4B—C7B	1.743 (2)
S4A—C7A	1.748 (2)	S5B—C7B	1.747 (2)
S5A—C7A	1.746 (3)	S5B—C8B	1.842 (3)
S5A—C8A	1.836 (2)	C2B—C7B	1.355 (3)
C2A—C7A	1.353 (3)	C3B—C4B	1.506 (3)
C3A—C4A	1.502 (3)	C4B—C5B	1.395 (3)
C4A—C5A	1.396 (3)	C4B—C9B	1.406 (3)
C4A—C9A	1.404 (3)	C5B—C6B	1.383 (4)
C5A—C6A	1.383 (4)	C6B—C11B	1.376 (4)
C6A—C11A	1.379 (4)	C8B—C9B	1.500 (3)
C8A—C9A	1.496 (3)	C9B—C10B	1.392 (3)
C9A—C10A	1.385 (3)	C10B—C11B	1.381 (3)
C10A—C11A	1.382 (4)
C1A—S2A—C2A	98.25 (12)	C1B—S2B—C2B	98.23 (12)
C1A—S2A—S4B	137.67 (9)	C1B—S2B—S2A^ii	132.86 (9)
C2A—S2A—S4B	103.26 (8)	C2B—S2B—S2A^ii	128.66 (9)
C1A—S2A—S2B^i	87.81 (9)	C2B—S3B—C3B	103.42 (11)
C2A—S2A—S2B^i	87.88 (8)	C1B—S4B—C7B	98.40 (12)
S4B—S2A—S2B^i	128.59 (3)	C1B—S4B—S2A	149.32 (9)
C2A—S3A—C3A	104.81 (11)	C7B—S4B—S2A	96.82 (8)
C1A—S4A—C7A	98.21 (12)	C7B—S5B—C8B	103.37 (11)
C7A—S5A—C8A	103.03 (11)	S1B—C1B—S2B	125.42 (15)
S1A—C1A—S2A	125.05 (17)	S1B—C1B—S4B	122.83 (16)
S1A—C1A—S4A	123.12 (16)	S2B—C1B—S4B	111.74 (13)
S2A—C1A—S4A	111.78 (14)	C7B—C2B—S3B	125.24 (19)
C7A—C2A—S3A	125.47 (19)	C7B—C2B—S2B	115.63 (18)
C7A—C2A—S2A	115.93 (18)	S3B—C2B—S2B	118.94 (14)
S3A—C2A—S2A	118.34 (14)	C4B—C3B—S3B	115.48 (18)
C4A—C3A—S3A	115.85 (17)	C5B—C4B—C9B	118.3 (2)
C5A—C4A—C9A	118.5 (2)	C5B—C4B—C3B	118.8 (2)
C5A—C4A—C3A	118.7 (2)	C9B—C4B—C3B	122.9 (2)
C9A—C4A—C3A	122.7 (2)	C6B—C5B—C4B	121.5 (2)
C6A—C5A—C4A	121.4 (2)	C11B—C6B—C5B	120.0 (2)
C11A—C6A—C5A	119.5 (2)	C2B—C7B—S4B	115.76 (18)
C2A—C7A—S5A	129.31 (19)	C2B—C7B—S5B	128.85 (19)
C2A—C7A—S4A	115.62 (19)	S4B—C7B—S5B	115.37 (14)
S5A—C7A—S4A	115.07 (14)	C9B—C8B—S5B	111.83 (17)
C9A—C8A—S5A	114.06 (17)	C10B—C9B—C4B	119.4 (2)
C10A—C9A—C4A	119.3 (2)	C10B—C9B—C8B	119.1 (2)
C10A—C9A—C8A	119.5 (2)	C4B—C9B—C8B	121.5 (2)
C4A—C9A—C8A	121.2 (2)	C11B—C10B—C9B	121.3 (2)
C11A—C10A—C9A	121.3 (2)	C6B—C11B—C10B	119.6 (2)
C6A—C11A—C10A	119.8 (2)
C2A—S2A—C1A—S1A	178.05 (17)	C1A—S2A—S4B—C7B	54.73 (16)
S4B—S2A—C1A—S1A	−61.7 (2)	C2A—S2A—S4B—C7B	173.26 (11)
S2B^i—S2A—C1A—S1A	90.51 (17)	S2B^i—S2A—S4B—C7B	−88.74 (8)
C2A—S2A—C1A—S4A	−4.60 (16)	C2B—S2B—C1B—S1B	176.40 (17)
S4B—S2A—C1A—S4A	115.62 (13)	S2A^ii—S2B—C1B—S1B	−9.1 (2)
S2B^i—S2A—C1A—S4A	−92.13 (12)	C2B—S2B—C1B—S4B	−4.63 (16)
C7A—S4A—C1A—S1A	−178.29 (17)	S2A^ii—S2B—C1B—S4B	169.84 (6)
C7A—S4A—C1A—S2A	4.29 (16)	C7B—S4B—C1B—S1B	−176.40 (16)
C3A—S3A—C2A—C7A	86.3 (2)	S2A—S4B—C1B—S1B	64.6 (3)
C3A—S3A—C2A—S2A	−99.86 (15)	C7B—S4B—C1B—S2B	4.60 (16)
C1A—S2A—C2A—C7A	3.3 (2)	S2A—S4B—C1B—S2B	−114.36 (15)
S4B—S2A—C2A—C7A	−139.96 (17)	C3B—S3B—C2B—C7B	86.0 (2)
S2B^i—S2A—C2A—C7A	90.81 (19)	C3B—S3B—C2B—S2B	−99.32 (16)
C1A—S2A—C2A—S3A	−171.09 (14)	C1B—S2B—C2B—C7B	3.0 (2)
S4B—S2A—C2A—S3A	45.63 (14)	S2A^ii—S2B—C2B—C7B	−171.86 (14)
S2B^i—S2A—C2A—S3A	−83.61 (13)	C1B—S2B—C2B—S3B	−172.25 (15)
C2A—S3A—C3A—C4A	−14.4 (2)	S2A^ii—S2B—C2B—S3B	12.9 (2)
S3A—C3A—C4A—C5A	121.3 (2)	C2B—S3B—C3B—C4B	−17.3 (2)
S3A—C3A—C4A—C9A	−62.0 (3)	S3B—C3B—C4B—C5B	118.4 (2)
C9A—C4A—C5A—C6A	1.1 (4)	S3B—C3B—C4B—C9B	−63.2 (3)
C3A—C4A—C5A—C6A	177.9 (2)	C9B—C4B—C5B—C6B	−0.6 (4)
C4A—C5A—C6A—C11A	0.6 (4)	C3B—C4B—C5B—C6B	177.8 (2)
S3A—C2A—C7A—S5A	−7.5 (4)	C4B—C5B—C6B—C11B	0.2 (4)
S2A—C2A—C7A—S5A	178.54 (14)	S3B—C2B—C7B—S4B	174.76 (14)
S3A—C2A—C7A—S4A	173.22 (13)	S2B—C2B—C7B—S4B	−0.1 (3)
S2A—C2A—C7A—S4A	−0.7 (3)	S3B—C2B—C7B—S5B	−3.4 (3)
C8A—S5A—C7A—C2A	−46.2 (3)	S2B—C2B—C7B—S5B	−178.28 (14)
C8A—S5A—C7A—S4A	133.08 (14)	C1B—S4B—C7B—C2B	−2.8 (2)
C1A—S4A—C7A—C2A	−2.2 (2)	S2A—S4B—C7B—C2B	150.49 (18)
C1A—S4A—C7A—S5A	178.41 (14)	C1B—S4B—C7B—S5B	175.63 (13)
C7A—S5A—C8A—C9A	−35.6 (2)	S2A—S4B—C7B—S5B	−31.09 (13)
C5A—C4A—C9A—C10A	−1.8 (3)	C8B—S5B—C7B—C2B	−49.2 (3)
C3A—C4A—C9A—C10A	−178.5 (2)	C8B—S5B—C7B—S4B	132.60 (14)
C5A—C4A—C9A—C8A	177.3 (2)	C7B—S5B—C8B—C9B	−35.1 (2)
C3A—C4A—C9A—C8A	0.6 (3)	C5B—C4B—C9B—C10B	0.8 (3)
S5A—C8A—C9A—C10A	−80.4 (3)	C3B—C4B—C9B—C10B	−177.6 (2)
S5A—C8A—C9A—C4A	100.5 (2)	C5B—C4B—C9B—C8B	−178.0 (2)
C4A—C9A—C10A—C11A	0.9 (4)	C3B—C4B—C9B—C8B	3.7 (4)
C8A—C9A—C10A—C11A	−178.3 (2)	S5B—C8B—C9B—C10B	−80.9 (3)
C5A—C6A—C11A—C10A	−1.6 (4)	S5B—C8B—C9B—C4B	97.9 (2)
C9A—C10A—C11A—C6A	0.8 (4)	C4B—C9B—C10B—C11B	−0.6 (4)
C1A—S2A—S4B—C1B	174.1 (2)	C8B—C9B—C10B—C11B	178.2 (2)
C2A—S2A—S4B—C1B	−67.40 (19)	C5B—C6B—C11B—C10B	0.0 (4)
S2B^i—S2A—S4B—C1B	30.61 (18)	C9B—C10B—C11B—C6B	0.2 (4)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.