Intramolecular and intermolecular geometry of thiophenes with oxygen-containing substituents

The intramolecular and intermolecular geometries of six thiophenes carrying oxygen-containing substituents have been determined. Crystals of 2-methoxythiophene and 3-methoxythiophene were grown in situ on a diffractometer from liquid samples. The 2-methoxy group introduces significant distortions to the thiophene nucleus and each molecule participates in four S...O contacts leading to an infinite bilayer. The extended structure of 3-methoxythiophene comprises zigzag chains of molecules linked by S...O contacts. Molecules of 2-acetyl-3-methoxythiophene are arranged in pairs about inversion centres, with ring centroids 3.835 Å apart. 5-Cyano-3-hydroxythiophene adopts the hydroxythiophene tautomeric form which allows conjugation between the S atom and the nitrile group: O—H...N hydrogen bonding leads to chains which are cross-linked by S...O contacts to give infinite two-dimensional layers. 5-(Methylthio)thiophen-3(2H)-one exists exclusively as the thiophen-3(2H)-one form in the solid state, allowing maximum conjugative interaction of both the ring heteroatom and the substituent with the carbonyl group: each molecule is linked to two of its neighbours through pairwise C—H...O interactions, forming ribbons. Spiro­[cyclohexane-1,2′-2′,3′-dihydrothiophen]-3′-one crystallizes with four independent molecules in the asymmetric unit with only minor differences between these: the five- and six-membered rings in each molecule are approximately orthogonal and C—H...O hydrogen bonding generates chains. The last two structures differ from the others in that they lack a fully aromatic thiophene system.

Computing details

Data collection: DIF4 (Stoe & Cie, 1992a) for (1), (2); DIF4 for (3), (4); DIF4 (Stoe & Cie, 1988a) for (5), (6). Cell refinement: DIF4 for (1), (2), (3), (4); DIF4 (Stoe & Cie, 1988a) for (5), (6). Data reduction: REDU4 (Stoe & Cie, 1992b) for (1), (2); REDU4 for (3), (4); REDU4 (Stoe & Cie, 1988B) for (5); REDU4 (Stoe & Cie, 1988b) for (6). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for (1), (2), (3); SHELXS86 (Sheldrick, 1990) for (4), (5), (6). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (1), (2), (3); SHELXL93 (Sheldrick, 1993) for (4), (5); SHELXL96 (Sheldrick, 1996) for (6). Molecular graphics: SHELXTL/PC (Sheldrick, 1994) for (1), (2), (5), (6); SHELXTL/PC for (3), (4). Software used to prepare material for publication: SHELXL97 for (1), (2), (3), (4); SHELXL93 (Sheldrick, 1993) for (5); SHELXL96 (Sheldrick, 1996) for (6).

(1)

Crystal data

C5H6OS	F(000) = 240
Mr = 114.16	Dx = 1.375 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 36 reflections
a = 6.848 (3) Å	θ = 15–19°
b = 7.540 (4) Å	µ = 0.45 mm^−1
c = 11.111 (5) Å	T = 100 K
β = 106.010 (5)°	Cylinder, colourless
V = 551.5 (5) Å^3	0.50 × 0.32 × 0.32 mm
Z = 4

Data collection

Stoe Stadi-4 four-circle diffractometer	Rint = 0.065
Radiation source: fine-focus sealed tube	θmax = 30.1°, θmin = 3.3°
Graphite monochromator	h = −9→9
ω/2θ scans	k = −9→10
1972 measured reflections	l = 0→15
1609 independent reflections	3 standard reflections every 60 min
1414 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: DIFMAP
R[F^2 > 2σ(F^2)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.123	Calculated w = 1/[σ^2(Fo^2) + (0.066P)^2 + 0.264P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.004
1609 reflections	Δρmax = 0.57 e Å^−3
88 parameters	Δρmin = −0.44 e Å^−3
2 restraints

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.

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

	x	y	z	Uiso*/Ueq
S1	0.18595 (6)	0.35080 (6)	0.20192 (4)	0.02182 (16)
C2	−0.0034 (2)	0.4990 (2)	0.20667 (16)	0.0180 (3)
C3	0.0200 (3)	0.5712 (2)	0.32569 (17)	0.0225 (3)
H3	−0.066 (3)	0.6520 (11)	0.345 (3)	0.038 (7)*
C4	0.2001 (3)	0.4985 (3)	0.41093 (17)	0.0287 (4)
H4	0.252 (4)	0.521 (4)	0.497 (3)	0.034 (6)*
C5	0.3012 (3)	0.3807 (3)	0.35841 (17)	0.0248 (4)
H5	0.426 (4)	0.323 (3)	0.393 (2)	0.019 (5)*
O2	−0.1460 (2)	0.52805 (18)	0.09733 (12)	0.0233 (3)
C2M	−0.3052 (3)	0.6463 (3)	0.1064 (2)	0.0300 (4)
H2M1	−0.384 (5)	0.651 (4)	0.026 (3)	0.045 (8)*
H2M2	−0.381 (5)	0.590 (4)	0.170 (3)	0.039 (7)*
H2M3	−0.242 (4)	0.758 (4)	0.131 (3)	0.042 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0208 (2)	0.0218 (2)	0.0229 (2)	0.00491 (15)	0.00598 (16)	−0.00114 (14)
C2	0.0176 (7)	0.0167 (7)	0.0221 (7)	0.0017 (5)	0.0095 (6)	0.0014 (5)
C3	0.0221 (8)	0.0230 (8)	0.0253 (8)	−0.0043 (6)	0.0114 (6)	−0.0003 (6)
C4	0.0296 (9)	0.0367 (10)	0.0211 (8)	−0.0115 (8)	0.0093 (7)	−0.0064 (7)
C5	0.0207 (8)	0.0290 (9)	0.0229 (8)	−0.0043 (7)	0.0031 (6)	0.0021 (6)
O2	0.0216 (6)	0.0270 (6)	0.0230 (6)	0.0109 (5)	0.0090 (5)	0.0045 (5)
C2M	0.0245 (9)	0.0281 (9)	0.0412 (11)	0.0117 (7)	0.0155 (8)	0.0078 (8)

Geometric parameters (Å, º)

S1—C5	1.715 (2)	C3—C4	1.440 (3)
S1—C2	1.7232 (17)	C4—C5	1.353 (3)
C2—O2	1.350 (2)	O2—C2M	1.433 (2)
C2—C3	1.398 (2)
C5—S1—C2	91.35 (9)	C2—C3—C4	109.11 (16)
O2—C2—C3	130.79 (16)	C5—C4—C3	114.43 (17)
O2—C2—S1	116.20 (12)	C4—C5—S1	112.10 (15)
C3—C2—S1	113.01 (13)	C2—O2—C2M	114.42 (15)
C5—S1—C2—O2	179.32 (14)	C3—C4—C5—S1	0.4 (2)
C5—S1—C2—C3	0.12 (14)	C2—S1—C5—C4	−0.27 (15)
O2—C2—C3—C4	−179.01 (17)	C3—C2—O2—C2M	−3.5 (3)
S1—C2—C3—C4	0.05 (18)	S1—C2—O2—C2M	177.51 (13)
C2—C3—C4—C5	−0.3 (2)

(2)

Crystal data

C5H6OS	Dx = 1.385 Mg m^−3
Mr = 114.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 15 reflections
a = 6.641 (4) Å	θ = 14–16°
b = 7.109 (4) Å	µ = 0.46 mm^−1
c = 11.594 (5) Å	T = 100 K
V = 547.4 (5) Å^3	Cylinder, colourless
Z = 4	0.8 × 0.5 × 0.5 mm
F(000) = 240

Data collection

Stoe Stadi-4 four-circle diffractometer	1377 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 30.0°, θmin = 3.4°
ω/2θ scans	h = −9→9
Absorption correction: ψ scans	k = 0→9
Tmin = 0.624, Tmax = 0.693	l = 0→16
1714 measured reflections	3 standard reflections every 60 min
1560 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.049	Calculated w = 1/[σ^2(Fo^2) + (0.089P)^2 + 0.49P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.143	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.34 e Å^−3
1560 reflections	Δρmin = −0.46 e Å^−3
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.004 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.05 (16)

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.

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

	x	y	z	Uiso*/Ueq
S1	0.79803 (12)	0.12176 (11)	0.80405 (6)	0.0221 (2)
C2	0.9723 (4)	0.1199 (4)	0.6954 (2)	0.0181 (5)
H2	1.070 (6)	0.186 (6)	0.700 (3)	0.013 (8)*
C3	0.9123 (4)	0.0047 (4)	0.6070 (2)	0.0146 (5)
C4	0.7221 (5)	−0.0815 (4)	0.6274 (2)	0.0163 (5)
H4	0.675 (7)	−0.155 (7)	0.580 (4)	0.027 (11)*
C5	0.6427 (5)	−0.0303 (4)	0.7329 (2)	0.0183 (5)
H5	0.546 (7)	−0.052 (6)	0.759 (4)	0.016 (10)*
O3	1.0134 (4)	−0.0314 (3)	0.50728 (18)	0.0202 (5)
C3M	1.1971 (6)	0.0697 (5)	0.4939 (3)	0.0251 (6)
H3M1	1.247 (7)	0.028 (6)	0.425 (4)	0.023 (10)*
H3M2	1.280 (7)	0.032 (6)	0.546 (3)	0.023 (10)*
H3M3	1.168 (10)	0.200 (9)	0.483 (5)	0.053 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0250 (4)	0.0236 (3)	0.0177 (3)	−0.0003 (3)	−0.0008 (3)	−0.0059 (3)
C2	0.0202 (12)	0.0172 (11)	0.0170 (11)	−0.0039 (10)	−0.0008 (10)	−0.0024 (12)
C3	0.0170 (12)	0.0138 (11)	0.0131 (11)	0.0019 (9)	−0.0018 (9)	0.0013 (9)
C4	0.0169 (11)	0.0164 (11)	0.0157 (11)	−0.0014 (9)	−0.0037 (10)	−0.0004 (9)
C5	0.0192 (13)	0.0176 (13)	0.0182 (12)	0.0005 (10)	−0.0076 (10)	0.0000 (10)
O3	0.0214 (11)	0.0239 (10)	0.0153 (9)	−0.0026 (8)	0.0022 (8)	−0.0007 (8)
C3M	0.0195 (14)	0.0313 (15)	0.0245 (13)	−0.0050 (12)	0.0039 (12)	0.0035 (11)

Geometric parameters (Å, º)

S1—C5	1.706 (3)	C3—C4	1.424 (4)
S1—C2	1.710 (3)	C4—C5	1.380 (4)
C2—C3	1.372 (4)	O3—C3M	1.425 (4)
C3—O3	1.361 (3)
C5—S1—C2	92.76 (16)	C2—C3—C4	113.0 (2)
C3—C2—S1	111.0 (2)	C5—C4—C3	111.9 (2)
O3—C3—C2	127.2 (3)	C4—C5—S1	111.4 (2)
O3—C3—C4	119.8 (2)	C3—O3—C3M	114.8 (2)
C5—S1—C2—C3	−0.2 (2)	C3—C4—C5—S1	0.5 (3)
S1—C2—C3—O3	−179.7 (2)	C2—S1—C5—C4	−0.2 (2)
S1—C2—C3—C4	0.5 (3)	C2—C3—O3—C3M	−2.7 (4)
O3—C3—C4—C5	179.5 (2)	C4—C3—O3—C3M	177.1 (3)
C2—C3—C4—C5	−0.7 (3)

(3)

Crystal data

C7H8O2S	Z = 2
Mr = 156.19	F(000) = 164
Triclinic, P1	Dx = 1.396 Mg m^−3
a = 7.5941 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8219 (10) Å	Cell parameters from 52 reflections
c = 7.9811 (9) Å	θ = 11–13°
α = 63.112 (5)°	µ = 0.37 mm^−1
β = 64.660 (5)°	T = 293 K
γ = 89.636 (5)°	Block, colourless
V = 371.70 (8) Å^3	0.50 × 0.50 × 0.50 mm

Data collection

Stoe Stadi-4 four-circle diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube	θmax = 24.8°, θmin = 3.0°
Graphite monochromator	h = −8→8
ω/2θ scans	k = −7→9
1276 measured reflections	l = 0→9
1253 independent reflections	3 standard reflections every 60 min
1035 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.032	Calculated w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.05P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.088	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.25 e Å^−3
1253 reflections	Δρmin = −0.17 e Å^−3
124 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.026 (15)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	Uiso*/Ueq
S1	0.20186 (7)	0.74459 (8)	0.41900 (8)	0.0492 (2)
C2	0.4477 (3)	0.7519 (3)	0.3660 (3)	0.0365 (4)
C2A	0.5030 (3)	0.7646 (3)	0.5141 (3)	0.0379 (4)
O2A	0.3749 (2)	0.7564 (2)	0.6777 (2)	0.0540 (4)
C2M	0.7182 (3)	0.7905 (4)	0.4611 (4)	0.0523 (6)
H2B1	0.793 (4)	0.894 (4)	0.326 (5)	0.091 (10)*
H2B2	0.769 (5)	0.672 (5)	0.468 (5)	0.095 (9)*
H2B3	0.743 (4)	0.805 (4)	0.556 (5)	0.087 (9)*
C3	0.5597 (3)	0.7454 (3)	0.1789 (3)	0.0388 (4)
O3	0.75642 (19)	0.7482 (2)	0.1060 (2)	0.0518 (4)
C3M	0.8534 (4)	0.7177 (4)	−0.0727 (4)	0.0559 (6)
H3A1	0.783 (4)	0.591 (4)	−0.042 (4)	0.060 (6)*
H3A2	0.853 (4)	0.819 (4)	−0.193 (5)	0.070 (8)*
H3A3	0.982 (4)	0.716 (3)	−0.092 (4)	0.062 (7)*
C4	0.4434 (3)	0.7362 (3)	0.0824 (3)	0.0485 (5)
H4	0.489 (3)	0.735 (3)	−0.035 (4)	0.055 (6)*
C5	0.2508 (4)	0.7355 (3)	0.1949 (4)	0.0548 (6)
H5	0.141 (4)	0.732 (4)	0.160 (4)	0.070 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0323 (3)	0.0667 (4)	0.0563 (4)	0.0170 (2)	−0.0213 (2)	−0.0362 (3)
C2	0.0307 (9)	0.0394 (10)	0.0400 (10)	0.0103 (7)	−0.0164 (7)	−0.0207 (8)
C2A	0.0394 (10)	0.0386 (9)	0.0387 (10)	0.0119 (7)	−0.0190 (8)	−0.0212 (8)
O2A	0.0483 (9)	0.0751 (10)	0.0445 (8)	0.0161 (7)	−0.0179 (7)	−0.0382 (8)
C2M	0.0448 (12)	0.0715 (16)	0.0583 (14)	0.0171 (11)	−0.0308 (11)	−0.0399 (13)
C3	0.0359 (9)	0.0414 (10)	0.0367 (9)	0.0072 (7)	−0.0146 (8)	−0.0202 (8)
O3	0.0339 (7)	0.0789 (10)	0.0495 (8)	0.0156 (6)	−0.0148 (6)	−0.0419 (8)
C3M	0.0474 (13)	0.0686 (15)	0.0457 (12)	0.0155 (11)	−0.0096 (10)	−0.0357 (12)
C4	0.0507 (12)	0.0592 (13)	0.0436 (12)	0.0110 (9)	−0.0251 (10)	−0.0290 (10)
C5	0.0528 (13)	0.0659 (14)	0.0625 (14)	0.0159 (10)	−0.0380 (11)	−0.0347 (11)

Geometric parameters (Å, º)

S1—C5	1.699 (2)	C2A—C2M	1.492 (3)
S1—C2	1.7237 (17)	C3—O3	1.347 (2)
C2—C3	1.392 (3)	C3—C4	1.419 (3)
C2—C2A	1.454 (3)	O3—C3M	1.428 (2)
C2A—O2A	1.222 (2)	C4—C5	1.347 (3)
C5—S1—C2	91.63 (10)	O3—C3—C2	121.19 (17)
C3—C2—C2A	131.62 (17)	O3—C3—C4	126.43 (17)
C3—C2—S1	110.52 (14)	C2—C3—C4	112.39 (17)
C2A—C2—S1	117.86 (14)	C3—O3—C3M	117.10 (17)
O2A—C2A—C2	120.20 (17)	C5—C4—C3	112.05 (19)
O2A—C2A—C2M	120.89 (18)	C4—C5—S1	113.42 (17)
C2—C2A—C2M	118.91 (17)
C5—S1—C2—C3	−0.52 (16)	C2A—C2—C3—C4	−179.04 (19)
C5—S1—C2—C2A	179.06 (15)	S1—C2—C3—C4	0.5 (2)
C3—C2—C2A—O2A	−175.57 (19)	C2—C3—O3—C3M	172.84 (19)
S1—C2—C2A—O2A	5.0 (2)	C4—C3—O3—C3M	−7.2 (3)
C3—C2—C2A—C2M	5.3 (3)	O3—C3—C4—C5	179.94 (19)
S1—C2—C2A—C2M	−174.21 (16)	C2—C3—C4—C5	−0.1 (3)
C2A—C2—C3—O3	0.9 (3)	C3—C4—C5—S1	−0.3 (3)
S1—C2—C3—O3	−179.60 (14)	C2—S1—C5—C4	0.46 (19)

(4)

Crystal data

C5H3NOS	F(000) = 256
Mr = 125.14	Dx = 1.489 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.516 (2) Å	Cell parameters from 33 reflections
b = 8.332 (2) Å	θ = 14–16°
c = 9.059 (2) Å	µ = 0.46 mm^−1
β = 100.19 (3)°	T = 293 K
V = 558.3 (2) Å^3	Tapered column, brown
Z = 4	0.86 × 0.47 × 0.35 mm

Data collection

Stoe Stadi-4 four-circle diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.3°
Graphite monochromator	h = −8→8
ω/2θ scans	k = −9→9
1742 measured reflections	l = 0→10
984 independent reflections	3 standard reflections every 60 min
910 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	All H-atom parameters refined
wR(F^2) = 0.070	Calculated w = 1/[σ^2(Fo^2) + (0.04P)^2 + 0.148P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = −0.013
981 reflections	Δρmax = 0.19 e Å^−3
86 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (43)

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 on F² for ALL reflections except for 3 with very negative F² or 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 > σ(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
S1	0.14998 (5)	0.97733 (4)	0.35386 (4)	0.0250 (2)
C2	0.2093 (2)	1.1623 (2)	0.4274 (2)	0.0228 (3)
H2	0.175 (3)	1.252 (3)	0.374 (2)	0.040 (5)*
C3	0.3120 (2)	1.15200 (15)	0.56767 (15)	0.0198 (3)
O3	0.38079 (14)	1.27651 (13)	0.65667 (12)	0.0291 (3)
H3	0.346 (3)	1.354 (3)	0.615 (3)	0.050 (6)*
C4	0.3436 (2)	0.9927 (2)	0.6178 (2)	0.0207 (3)
H4	0.412 (2)	0.9658 (19)	0.713 (2)	0.031 (4)*
C5	0.2641 (2)	0.8850 (2)	0.51280 (14)	0.0207 (3)
C6	0.2663 (2)	0.7149 (2)	0.5250 (2)	0.0261 (3)
N7	0.2682 (2)	0.5775 (2)	0.53365 (15)	0.0375 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0316 (2)	0.0194 (2)	0.0211 (2)	−0.00103 (12)	−0.00294 (14)	−0.00003 (12)
C2	0.0271 (7)	0.0156 (6)	0.0247 (7)	0.0014 (5)	0.0021 (5)	0.0033 (6)
C3	0.0219 (6)	0.0151 (6)	0.0220 (7)	0.0004 (5)	0.0032 (5)	0.0005 (5)
O3	0.0407 (6)	0.0147 (5)	0.0284 (6)	−0.0021 (4)	−0.0036 (4)	−0.0020 (4)
C4	0.0225 (7)	0.0191 (7)	0.0200 (7)	0.0023 (5)	0.0024 (6)	0.0023 (5)
C5	0.0239 (6)	0.0162 (7)	0.0221 (7)	0.0014 (5)	0.0046 (5)	0.0017 (5)
C6	0.0352 (8)	0.0193 (8)	0.0238 (7)	0.0005 (6)	0.0054 (6)	−0.0009 (5)
N7	0.0578 (9)	0.0189 (7)	0.0359 (7)	0.0016 (6)	0.0084 (6)	0.0010 (6)

Geometric parameters (Å, º)

S1—C2	1.7062 (14)	C3—C4	1.409 (2)
S1—C5	1.7217 (13)	C4—C5	1.366 (2)
C2—C3	1.368 (2)	C5—C6	1.421 (2)
C3—O3	1.359 (2)	C6—N7	1.147 (2)
C2—S1—C5	91.15 (7)	C5—C4—C3	111.47 (12)
C3—C2—S1	111.82 (10)	C4—C5—C6	127.11 (13)
O3—C3—C2	126.62 (12)	C4—C5—S1	112.37 (11)
O3—C3—C4	120.19 (12)	C6—C5—S1	120.51 (10)
C2—C3—C4	113.18 (12)	N7—C6—C5	179.5 (2)
C5—S1—C2—C3	−0.05 (11)	C3—C4—C5—S1	−0.38 (14)
S1—C2—C3—O3	−179.96 (10)	C2—S1—C5—C4	0.25 (10)
S1—C2—C3—C4	−0.2 (2)	C2—S1—C5—C6	179.43 (11)
O3—C3—C4—C5	−179.84 (11)	C4—C5—C6—N7	−143 (18)
C2—C3—C4—C5	0.4 (2)	S1—C5—C6—N7	38 (18)
C3—C4—C5—C6	−179.49 (12)

(5)

Crystal data

C5H6OS2	Dx = 1.522 Mg m^−3
Mr = 146.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pn21a	Cell parameters from 50 reflections
a = 19.513 (6) Å	θ = 12.5–16.0°
b = 8.083 (2) Å	µ = 0.73 mm^−1
c = 4.046 (2) Å	T = 223 K
V = 638.2 (4) Å^3	Lath, colourless
Z = 4	1.30 × 0.40 × 0.20 mm
F(000) = 304

Data collection

Stoe Stadi-4 four-circle diffractometer	Rint = 0.049
Radiation source: fine-focus sealed tube	θmax = 22.6°, θmin = 2.1°
Graphite monochromator	h = −3→21
ω/2θ scans	k = −8→0
825 measured reflections	l = −4→4
463 independent reflections	3 standard reflections every 60 min
448 reflections with I > 2σ(I)	intensity decay: variation +−2.0%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	Riding model
R[F^2 > 2σ(F^2)] = 0.042	Calculated w = 1/[σ^2(Fo^2) + (0.068P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max = 0.001
S = 1.19	Δρmax = 0.46 e Å^−3
463 reflections	Δρmin = −0.33 e Å^−3
73 parameters	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
1 restraint	Absolute structure parameter: −0.01 (19)
Primary atom site location: structure-invariant direct methods

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 on F² for ALL reflections except for 0 with very negative F² or 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 > σ(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
S1	0.35111 (6)	0.6299 (2)	0.0255 (3)	0.0383 (4)
C2	0.4329 (2)	0.6828 (5)	−0.1568 (13)	0.0376 (11)
H2A	0.4265 (2)	0.7648 (5)	−0.3326 (13)	0.045*
H2B	0.4634 (2)	0.7300 (5)	0.0111 (13)	0.045*
C3	0.4635 (2)	0.5263 (6)	−0.2965 (13)	0.0345 (10)
O3	0.5194 (2)	0.5270 (5)	−0.4362 (10)	0.0501 (11)
C4	0.4207 (2)	0.3849 (6)	−0.2401 (11)	0.0310 (9)
H4	0.4321 (2)	0.2777 (6)	−0.3111 (11)	0.037*
C5	0.3628 (2)	0.4204 (6)	−0.0763 (11)	0.0301 (10)
S5	0.29713 (5)	0.29283 (14)	0.0514 (3)	0.0388 (4)
C5A	0.3289 (3)	0.0915 (7)	−0.0638 (14)	0.0459 (14)
H5A1	0.2957 (3)	0.0078 (7)	−0.0029 (14)	0.069*
H5A2	0.3718 (3)	0.0703 (7)	0.0501 (14)	0.069*
H5A3	0.3365 (3)	0.0881 (7)	−0.3007 (14)	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0359 (8)	0.0268 (7)	0.0520 (8)	0.0058 (6)	0.0054 (4)	−0.0026 (6)
C2	0.035 (2)	0.027 (2)	0.051 (3)	−0.005 (2)	0.001 (2)	0.004 (2)
C3	0.031 (2)	0.026 (2)	0.046 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
O3	0.040 (2)	0.037 (2)	0.074 (3)	−0.006 (2)	0.018 (2)	0.000 (2)
C4	0.028 (2)	0.022 (2)	0.043 (2)	0.0012 (14)	−0.001 (2)	0.000 (2)
C5	0.027 (2)	0.025 (2)	0.039 (2)	0.000 (2)	−0.006 (2)	−0.001 (2)
S5	0.0281 (7)	0.0367 (7)	0.0515 (8)	−0.0068 (5)	0.0040 (4)	0.0007 (8)
C5A	0.050 (3)	0.030 (3)	0.058 (3)	−0.011 (2)	0.002 (2)	−0.002 (2)

Geometric parameters (Å, º)

S1—C5	1.757 (5)	C3—C4	1.434 (6)
S1—C2	1.809 (4)	C4—C5	1.340 (6)
C2—C3	1.510 (7)	C5—S5	1.724 (5)
C3—O3	1.229 (6)	S5—C5A	1.803 (5)
C5—S1—C2	91.0 (2)	C5—C4—C3	113.5 (4)
C3—C2—S1	107.7 (3)	C4—C5—S5	130.3 (4)
O3—C3—C4	126.5 (4)	C4—C5—S1	115.6 (4)
O3—C3—C2	121.3 (4)	S5—C5—S1	114.1 (2)
C4—C3—C2	112.2 (3)	C5—S5—C5A	101.9 (2)
C5—S1—C2—C3	1.4 (3)	C3—C4—C5—S1	1.2 (5)
S1—C2—C3—O3	179.9 (4)	C2—S1—C5—C4	−1.6 (4)
S1—C2—C3—C4	−1.1 (5)	C2—S1—C5—S5	178.6 (3)
O3—C3—C4—C5	179.0 (4)	C4—C5—S5—C5A	4.3 (5)
C2—C3—C4—C5	0.0 (6)	S1—C5—S5—C5A	−175.9 (3)
C3—C4—C5—S5	−179.0 (3)

(6)

Crystal data

C9H12OS	F(000) = 1440
Mr = 168.25	Dx = 1.261 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.826 (2) Å	Cell parameters from 45 reflections
b = 17.065 (2) Å	θ = 12.5–15.0°
c = 19.190 (3) Å	µ = 0.31 mm^−1
β = 91.011 (12)°	T = 223 K
V = 3544.7 (10) Å^3	Block, pale yellow/green
Z = 16	0.54 × 0.54 × 0.46 mm

Data collection

Stoe Stadi-4 four-circle diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 22.5°, θmin = 1.6°
Graphite monochromator	h = −11→11
ω/2θ scans	k = 0→18
4638 measured reflections	l = 0→20
4638 independent reflections	3 standard reflections every 60 min
2978 reflections with I > 2σ(I)	intensity decay: 3.0%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	Riding model
R[F^2 > 2σ(F^2)] = 0.037	Calculated w = 1/[σ^2(Fo^2) + (0.054P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max = 0.003
S = 0.98	Δρmax = 0.26 e Å^−3
4638 reflections	Δρmin = −0.22 e Å^−3
398 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00018 (14)
Primary atom site location: structure-invariant direct methods

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. 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 > σ(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
S1A	0.48890 (6)	0.23093 (4)	0.62862 (4)	0.0497 (2)
C2A	0.3387 (2)	0.28110 (14)	0.62211 (12)	0.0391 (6)
C3A	0.2442 (2)	0.21988 (15)	0.64290 (15)	0.0518 (7)
O3A	0.13487 (17)	0.23646 (12)	0.64691 (13)	0.0790 (7)
C4A	0.2976 (3)	0.14399 (16)	0.65559 (17)	0.0676 (9)
H4A	0.2510	0.0994	0.6669	0.081*
C5A	0.4201 (3)	0.14357 (16)	0.64966 (17)	0.0638 (8)
H5A	0.4667	0.0977	0.6567	0.077*
C6A	0.3152 (2)	0.30817 (16)	0.54659 (13)	0.0546 (7)
H6A1	0.3285	0.2640	0.5150	0.066*
H6A2	0.2289	0.3247	0.5412	0.066*
C7A	0.3987 (3)	0.37519 (17)	0.52646 (14)	0.0638 (8)
H7A1	0.4842	0.3563	0.5252	0.077*
H7A2	0.3756	0.3931	0.4795	0.077*
C8A	0.3918 (3)	0.44328 (16)	0.57622 (15)	0.0615 (8)
H8A1	0.3091	0.4666	0.5733	0.074*
H8A2	0.4517	0.4834	0.5629	0.074*
C9A	0.4186 (2)	0.41732 (15)	0.65024 (14)	0.0522 (7)
H9A1	0.4073	0.4617	0.6819	0.063*
H1A2	0.5048	0.4002	0.6544	0.063*
C10A	0.3345 (2)	0.35089 (13)	0.67142 (13)	0.0409 (6)
H0A1	0.2494	0.3704	0.6731	0.049*
H0A2	0.3583	0.3335	0.7184	0.049*
S1B	0.00343 (6)	0.51431 (4)	0.86425 (4)	0.0558 (2)
C2B	0.1513 (2)	0.46187 (14)	0.87389 (13)	0.0413 (6)
C3B	0.2493 (2)	0.52264 (16)	0.85585 (15)	0.0550 (8)
O3B	0.35839 (18)	0.50449 (13)	0.85505 (14)	0.0931 (8)
C4B	0.1995 (3)	0.59875 (17)	0.84246 (17)	0.0659 (9)
H4B	0.2482	0.6428	0.8326	0.079*
C5B	0.0768 (3)	0.60078 (17)	0.84532 (16)	0.0654 (9)
H5B	0.0324	0.6474	0.8374	0.078*
C6B	0.1677 (3)	0.43310 (17)	0.94889 (14)	0.0609 (8)
H6B1	0.2528	0.4148	0.9560	0.073*
H6B2	0.1542	0.4770	0.9808	0.073*
C7B	0.0798 (3)	0.36748 (18)	0.96637 (15)	0.0672 (9)
H7B1	−0.0050	0.3877	0.9657	0.081*
H7B2	0.0985	0.3485	1.0136	0.081*
C8B	0.0886 (3)	0.29998 (17)	0.91561 (14)	0.0607 (8)
H8B1	0.1704	0.2757	0.9200	0.073*
H8B2	0.0266	0.2603	0.9268	0.073*
C9B	0.0678 (2)	0.32797 (15)	0.84188 (13)	0.0508 (7)
H9B1	−0.0173	0.3468	0.8363	0.061*
H9B2	0.0789	0.2840	0.8098	0.061*
C10B	0.1560 (2)	0.39315 (14)	0.82325 (13)	0.0431 (6)
H0B1	0.1356	0.4120	0.7762	0.052*
H0B2	0.2403	0.3723	0.8228	0.052*
S1C	0.74111 (6)	0.22897 (4)	0.85097 (4)	0.0605 (2)
C2C	0.5926 (2)	0.27917 (14)	0.86252 (12)	0.0388 (6)
C3C	0.4945 (2)	0.21858 (15)	0.84363 (14)	0.0470 (7)
O3C	0.38515 (16)	0.23521 (11)	0.84222 (12)	0.0716 (6)
C4C	0.5467 (3)	0.14278 (16)	0.82942 (17)	0.0632 (8)
H4C	0.4984	0.0984	0.8191	0.076*
C5C	0.6692 (3)	0.14127 (17)	0.83222 (16)	0.0652 (9)
H5C	0.7141	0.0950	0.8244	0.078*
C6C	0.5786 (3)	0.30273 (17)	0.93872 (13)	0.0571 (8)
H6C1	0.4932	0.3194	0.9462	0.069*
H6C2	0.5947	0.2570	0.9683	0.069*
C7C	0.6655 (3)	0.36852 (18)	0.96053 (15)	0.0686 (9)
H7C1	0.6483	0.3842	1.0085	0.082*
H7C2	0.7511	0.3498	0.9592	0.082*
C8C	0.6504 (3)	0.43870 (16)	0.91275 (14)	0.0639 (8)
H8C1	0.5675	0.4608	0.9179	0.077*
H8C2	0.7106	0.4791	0.9263	0.077*
C9C	0.6689 (2)	0.41639 (15)	0.83770 (13)	0.0533 (7)
H9C1	0.7546	0.3995	0.8315	0.064*
H9C2	0.6543	0.4623	0.8080	0.064*
C10C	0.5819 (2)	0.35080 (13)	0.81550 (13)	0.0418 (6)
H0C1	0.6002	0.3354	0.7676	0.050*
H0C2	0.4968	0.3702	0.8161	0.050*
S1D	−0.24780 (6)	0.51636 (5)	0.64729 (4)	0.0648 (3)
C2D	−0.1034 (2)	0.46420 (15)	0.63075 (13)	0.0431 (6)
C3D	−0.0010 (2)	0.52285 (15)	0.64706 (15)	0.0524 (7)
O3D	0.10718 (17)	0.50484 (12)	0.64581 (13)	0.0816 (7)
C4D	−0.0488 (3)	0.59912 (17)	0.66467 (18)	0.0733 (10)
H4D	0.0018	0.6427	0.6743	0.088*
C5D	−0.1714 (3)	0.60180 (17)	0.66587 (18)	0.0749 (10)
H5D	−0.2139	0.6482	0.6764	0.090*
C6D	−0.0979 (3)	0.44123 (18)	0.55390 (14)	0.0654 (8)
H6D1	−0.1161	0.4874	0.5251	0.079*
H6D2	−0.0139	0.4239	0.5435	0.079*
C7D	−0.1881 (3)	0.3765 (2)	0.53462 (16)	0.0802 (10)
H7D1	−0.2728	0.3958	0.5394	0.096*
H7D2	−0.1768	0.3616	0.4858	0.096*
C8D	−0.1693 (3)	0.30555 (18)	0.58056 (15)	0.0704 (9)
H8D1	−0.2311	0.2656	0.5684	0.084*
H8D2	−0.0873	0.2833	0.5727	0.084*
C9D	−0.1808 (3)	0.32760 (16)	0.65629 (14)	0.0566 (8)
H9D1	−0.1650	0.2814	0.6854	0.068*
H9D2	−0.2653	0.3454	0.6648	0.068*
C10D	−0.0906 (2)	0.39190 (14)	0.67651 (13)	0.0438 (6)
H0D1	−0.0062	0.3716	0.6733	0.053*
H0D2	−0.1041	0.4068	0.7251	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0305 (4)	0.0507 (4)	0.0679 (5)	0.0084 (3)	0.0040 (3)	−0.0015 (3)
C2A	0.0263 (13)	0.0428 (15)	0.0482 (15)	0.0026 (11)	−0.0018 (11)	−0.0038 (12)
C3A	0.0327 (16)	0.0449 (17)	0.078 (2)	−0.0034 (13)	0.0025 (14)	−0.0085 (14)
O3A	0.0301 (11)	0.0596 (13)	0.148 (2)	−0.0045 (10)	0.0084 (12)	−0.0021 (13)
C4A	0.0488 (19)	0.0455 (18)	0.109 (3)	−0.0084 (15)	0.0043 (17)	−0.0002 (17)
C5A	0.059 (2)	0.0405 (17)	0.092 (2)	0.0100 (14)	−0.0021 (17)	−0.0021 (15)
C6A	0.0527 (17)	0.0630 (19)	0.0478 (17)	0.0097 (15)	−0.0098 (13)	−0.0119 (14)
C7A	0.070 (2)	0.076 (2)	0.0453 (17)	0.0101 (17)	0.0033 (15)	0.0106 (16)
C8A	0.0611 (19)	0.0495 (18)	0.074 (2)	0.0037 (15)	0.0109 (15)	0.0135 (16)
C9A	0.0506 (17)	0.0420 (16)	0.0639 (19)	−0.0047 (13)	0.0005 (14)	−0.0050 (14)
C10A	0.0354 (14)	0.0425 (15)	0.0446 (15)	0.0037 (12)	0.0009 (11)	−0.0037 (12)
S1B	0.0324 (4)	0.0527 (5)	0.0824 (5)	0.0111 (3)	0.0039 (3)	−0.0076 (4)
C2B	0.0284 (13)	0.0429 (15)	0.0524 (16)	0.0043 (12)	−0.0042 (11)	−0.0088 (13)
C3B	0.0314 (16)	0.0491 (18)	0.084 (2)	−0.0011 (13)	−0.0070 (14)	−0.0106 (15)
O3B	0.0313 (13)	0.0670 (15)	0.181 (3)	−0.0045 (10)	−0.0033 (13)	0.0017 (15)
C4B	0.052 (2)	0.0451 (18)	0.100 (3)	−0.0023 (15)	0.0016 (17)	−0.0040 (16)
C5B	0.058 (2)	0.0447 (18)	0.093 (2)	0.0158 (15)	−0.0016 (17)	−0.0077 (16)
C6B	0.0636 (19)	0.067 (2)	0.0518 (18)	0.0077 (16)	−0.0159 (14)	−0.0152 (15)
C7B	0.076 (2)	0.076 (2)	0.0487 (18)	0.0043 (18)	−0.0001 (15)	0.0050 (17)
C8B	0.0653 (19)	0.0525 (18)	0.064 (2)	0.0002 (15)	−0.0054 (15)	0.0097 (16)
C9B	0.0556 (18)	0.0420 (16)	0.0543 (18)	−0.0020 (13)	−0.0108 (14)	−0.0068 (13)
C10B	0.0395 (15)	0.0477 (16)	0.0422 (15)	0.0076 (13)	0.0007 (12)	−0.0071 (12)
S1C	0.0298 (4)	0.0595 (5)	0.0920 (6)	0.0064 (3)	−0.0025 (4)	0.0111 (4)
C2C	0.0287 (13)	0.0414 (15)	0.0463 (15)	0.0007 (11)	−0.0007 (11)	0.0052 (12)
C3C	0.0341 (15)	0.0428 (16)	0.0640 (18)	−0.0047 (13)	−0.0010 (13)	0.0081 (13)
O3C	0.0294 (11)	0.0525 (12)	0.133 (2)	−0.0065 (9)	−0.0043 (11)	−0.0104 (12)
C4C	0.0520 (19)	0.0401 (17)	0.097 (2)	−0.0003 (14)	−0.0064 (16)	−0.0021 (16)
C5C	0.060 (2)	0.0479 (18)	0.088 (2)	0.0157 (15)	0.0052 (17)	0.0071 (16)
C6C	0.0629 (18)	0.0619 (19)	0.0465 (17)	−0.0090 (15)	0.0025 (14)	0.0101 (14)
C7C	0.080 (2)	0.081 (2)	0.0450 (17)	−0.0205 (18)	−0.0137 (16)	0.0021 (16)
C8C	0.069 (2)	0.0539 (18)	0.068 (2)	−0.0196 (16)	−0.0184 (16)	−0.0031 (15)
C9C	0.0518 (18)	0.0508 (17)	0.0571 (19)	−0.0144 (14)	−0.0048 (14)	0.0138 (14)
C10C	0.0404 (15)	0.0422 (15)	0.0428 (15)	−0.0019 (12)	−0.0057 (12)	0.0041 (12)
S1D	0.0300 (4)	0.0629 (5)	0.1014 (7)	0.0094 (3)	0.0002 (4)	0.0144 (4)
C2D	0.0257 (13)	0.0469 (16)	0.0567 (17)	0.0019 (12)	0.0001 (11)	0.0094 (13)
C3D	0.0319 (16)	0.0421 (17)	0.083 (2)	0.0002 (13)	−0.0019 (14)	0.0096 (14)
O3D	0.0298 (12)	0.0557 (13)	0.159 (2)	−0.0036 (10)	−0.0011 (12)	−0.0101 (13)
C4D	0.050 (2)	0.0442 (19)	0.125 (3)	−0.0005 (15)	−0.0114 (19)	0.0023 (18)
C5D	0.060 (2)	0.0473 (19)	0.118 (3)	0.0204 (16)	−0.0005 (19)	0.0081 (18)
C6D	0.065 (2)	0.079 (2)	0.0536 (19)	−0.0075 (17)	0.0100 (15)	0.0203 (16)
C7D	0.089 (3)	0.105 (3)	0.0464 (19)	−0.022 (2)	−0.0126 (17)	−0.0024 (18)
C8D	0.069 (2)	0.068 (2)	0.075 (2)	−0.0214 (17)	−0.0042 (17)	−0.0142 (18)
C9D	0.0563 (18)	0.0527 (18)	0.061 (2)	−0.0088 (14)	−0.0036 (14)	0.0094 (14)
C10D	0.0407 (15)	0.0449 (16)	0.0455 (16)	0.0006 (12)	−0.0056 (12)	0.0027 (12)

Geometric parameters (Å, º)

S1A—C5A	1.718 (3)	S1C—C5C	1.722 (3)
S1A—C2A	1.840 (2)	S1C—C2C	1.839 (2)
C2A—C3A	1.520 (4)	C2C—C3C	1.521 (3)
C2A—C10A	1.522 (3)	C2C—C10C	1.522 (3)
C2A—C6A	1.538 (3)	C2C—C6C	1.527 (3)
C3A—O3A	1.221 (3)	C3C—O3C	1.218 (3)
C3A—C4A	1.437 (4)	C3C—C4C	1.439 (4)
C4A—C5A	1.334 (4)	C4C—C5C	1.326 (4)
C6A—C7A	1.513 (4)	C6C—C7C	1.519 (4)
C7A—C8A	1.507 (4)	C7C—C8C	1.516 (4)
C8A—C9A	1.511 (4)	C8C—C9C	1.506 (4)
C9A—C10A	1.514 (3)	C9C—C10C	1.519 (3)
S1B—C5B	1.718 (3)	S1D—C5D	1.711 (3)
S1B—C2B	1.840 (2)	S1D—C2D	1.831 (3)
C2B—C10B	1.525 (3)	C2D—C3D	1.522 (4)
C2B—C3B	1.528 (4)	C2D—C10D	1.519 (3)
C2B—C6B	1.528 (4)	C2D—C6D	1.528 (4)
C3B—O3B	1.221 (3)	C3D—O3D	1.212 (3)
C3B—C4B	1.428 (4)	C3D—C4D	1.443 (4)
C4B—C5B	1.330 (4)	C4D—C5D	1.328 (4)
C6B—C7B	1.511 (4)	C6D—C7D	1.516 (4)
C7B—C8B	1.512 (4)	C7D—C8D	1.509 (4)
C8B—C9B	1.507 (4)	C8D—C9D	1.509 (4)
C9B—C10B	1.512 (3)	C9D—C10D	1.515 (3)
C5A—S1A—C2A	91.93 (13)	C5C—S1C—C2C	92.11 (13)
C3A—C2A—C10A	110.3 (2)	C3C—C2C—C10C	111.06 (19)
C3A—C2A—C6A	110.6 (2)	C3C—C2C—C6C	109.1 (2)
C10A—C2A—C6A	110.1 (2)	C10C—C2C—C6C	110.4 (2)
C3A—C2A—S1A	105.09 (17)	C3C—C2C—S1C	105.23 (17)
C10A—C2A—S1A	111.00 (16)	C10C—C2C—S1C	111.09 (17)
C6A—C2A—S1A	109.59 (17)	C6C—C2C—S1C	109.87 (17)
O3A—C3A—C4A	125.8 (3)	O3C—C3C—C4C	126.2 (2)
O3A—C3A—C2A	121.0 (2)	O3C—C3C—C2C	121.4 (2)
C4A—C3A—C2A	113.2 (2)	C4C—C3C—C2C	112.4 (2)
C5A—C4A—C3A	112.8 (3)	C5C—C4C—C3C	113.9 (3)
C4A—C5A—S1A	116.8 (2)	C4C—C5C—S1C	116.1 (2)
C7A—C6A—C2A	112.2 (2)	C7C—C6C—C2C	112.8 (2)
C8A—C7A—C6A	112.6 (2)	C6C—C7C—C8C	111.0 (2)
C7A—C8A—C9A	111.0 (2)	C7C—C8C—C9C	111.3 (2)
C8A—C9A—C10A	111.4 (2)	C8C—C9C—C10C	111.2 (2)
C9A—C10A—C2A	113.2 (2)	C9C—C10C—C2C	112.66 (19)
C5B—S1B—C2B	91.96 (13)	C5D—S1D—C2D	92.25 (13)
C10B—C2B—C3B	110.3 (2)	C3D—C2D—C10D	110.88 (19)
C10B—C2B—C6B	110.4 (2)	C3D—C2D—C6D	109.0 (2)
C3B—C2B—C6B	111.2 (2)	C10D—C2D—C6D	110.2 (2)
C10B—C2B—S1B	110.40 (16)	C3D—C2D—S1D	105.40 (18)
C3B—C2B—S1B	104.70 (17)	C10D—C2D—S1D	111.34 (17)
C6B—C2B—S1B	109.71 (18)	C6D—C2D—S1D	109.88 (17)
O3B—C3B—C4B	126.2 (3)	O3D—C3D—C4D	125.7 (3)
O3B—C3B—C2B	120.4 (2)	O3D—C3D—C2D	122.0 (2)
C4B—C3B—C2B	113.3 (2)	C4D—C3D—C2D	112.2 (2)
C5B—C4B—C3B	113.0 (3)	C5D—C4D—C3D	113.4 (3)
C4B—C5B—S1B	116.9 (2)	C4D—C5D—S1D	116.5 (2)
C7B—C6B—C2B	112.6 (2)	C7D—C6D—C2D	112.7 (2)
C6B—C7B—C8B	112.0 (2)	C6D—C7D—C8D	111.2 (2)
C9B—C8B—C7B	110.7 (2)	C7D—C8D—C9D	110.5 (3)
C8B—C9B—C10B	111.8 (2)	C8D—C9D—C10D	111.3 (2)
C9B—C10B—C2B	112.8 (2)	C9D—C10D—C2D	112.9 (2)
C5A—S1A—C2A—C3A	3.4 (2)	C5C—S1C—C2C—C3C	−4.48 (18)
C5A—S1A—C2A—C10A	122.6 (2)	C5C—S1C—C2C—C10C	−124.75 (19)
C5A—S1A—C2A—C6A	−115.5 (2)	C5C—S1C—C2C—C6C	112.80 (19)
C10A—C2A—C3A—O3A	56.9 (3)	C10C—C2C—C3C—O3C	−55.5 (3)
C6A—C2A—C3A—O3A	−65.2 (3)	C6C—C2C—C3C—O3C	66.4 (3)
S1A—C2A—C3A—O3A	176.6 (2)	S1C—C2C—C3C—O3C	−175.8 (2)
C10A—C2A—C3A—C4A	−123.8 (3)	C10C—C2C—C3C—C4C	125.3 (3)
C6A—C2A—C3A—C4A	114.1 (3)	C6C—C2C—C3C—C4C	−112.9 (3)
S1A—C2A—C3A—C4A	−4.1 (3)	S1C—C2C—C3C—C4C	5.0 (3)
O3A—C3A—C4A—C5A	−177.9 (3)	O3C—C3C—C4C—C5C	177.8 (3)
C2A—C3A—C4A—C5A	2.9 (4)	C2C—C3C—C4C—C5C	−3.0 (4)
C3A—C4A—C5A—S1A	0.0 (4)	C3C—C4C—C5C—S1C	−0.7 (4)
C2A—S1A—C5A—C4A	−2.2 (3)	C2C—S1C—C5C—C4C	3.3 (3)
C3A—C2A—C6A—C7A	173.9 (2)	C3C—C2C—C6C—C7C	−174.9 (2)
C10A—C2A—C6A—C7A	51.8 (3)	C10C—C2C—C6C—C7C	−52.6 (3)
S1A—C2A—C6A—C7A	−70.6 (2)	S1C—C2C—C6C—C7C	70.3 (3)
C2A—C6A—C7A—C8A	−54.1 (3)	C2C—C6C—C7C—C8C	54.6 (3)
C6A—C7A—C8A—C9A	55.0 (3)	C6C—C7C—C8C—C9C	−55.9 (3)
C7A—C8A—C9A—C10A	−54.8 (3)	C7C—C8C—C9C—C10C	56.1 (3)
C8A—C9A—C10A—C2A	54.9 (3)	C8C—C9C—C10C—C2C	−55.0 (3)
C3A—C2A—C10A—C9A	−175.1 (2)	C3C—C2C—C10C—C9C	173.7 (2)
C6A—C2A—C10A—C9A	−52.7 (3)	C6C—C2C—C10C—C9C	52.6 (3)
S1A—C2A—C10A—C9A	68.9 (2)	S1C—C2C—C10C—C9C	−69.6 (2)
C5B—S1B—C2B—C10B	−121.8 (2)	C5D—S1D—C2D—C3D	3.6 (2)
C5B—S1B—C2B—C3B	−3.1 (2)	C5D—S1D—C2D—C10D	123.9 (2)
C5B—S1B—C2B—C6B	116.3 (2)	C5D—S1D—C2D—C6D	−113.8 (2)
C10B—C2B—C3B—O3B	−58.6 (3)	C10D—C2D—C3D—O3D	54.3 (4)
C6B—C2B—C3B—O3B	64.3 (3)	C6D—C2D—C3D—O3D	−67.1 (3)
S1B—C2B—C3B—O3B	−177.3 (3)	S1D—C2D—C3D—O3D	174.9 (2)
C10B—C2B—C3B—C4B	122.6 (3)	C10D—C2D—C3D—C4D	−124.7 (3)
C6B—C2B—C3B—C4B	−114.6 (3)	C6D—C2D—C3D—C4D	113.9 (3)
S1B—C2B—C3B—C4B	3.9 (3)	S1D—C2D—C3D—C4D	−4.0 (3)
O3B—C3B—C4B—C5B	178.5 (3)	O3D—C3D—C4D—C5D	−176.3 (3)
C2B—C3B—C4B—C5B	−2.8 (4)	C2D—C3D—C4D—C5D	2.6 (4)
C3B—C4B—C5B—S1B	0.2 (4)	C3D—C4D—C5D—S1D	0.4 (4)
C2B—S1B—C5B—C4B	1.9 (3)	C2D—S1D—C5D—C4D	−2.5 (3)
C10B—C2B—C6B—C7B	−51.9 (3)	C3D—C2D—C6D—C7D	174.0 (2)
C3B—C2B—C6B—C7B	−174.6 (2)	C10D—C2D—C6D—C7D	52.1 (3)
S1B—C2B—C6B—C7B	70.0 (3)	S1D—C2D—C6D—C7D	−70.9 (3)
C2B—C6B—C7B—C8B	54.4 (3)	C2D—C6D—C7D—C8D	−55.2 (4)
C6B—C7B—C8B—C9B	−55.5 (3)	C6D—C7D—C8D—C9D	56.6 (4)
C7B—C8B—C9B—C10B	55.5 (3)	C7D—C8D—C9D—C10D	−56.7 (3)
C8B—C9B—C10B—C2B	−54.9 (3)	C8D—C9D—C10D—C2D	55.4 (3)
C3B—C2B—C10B—C9B	175.4 (2)	C3D—C2D—C10D—C9D	−173.0 (2)
C6B—C2B—C10B—C9B	52.1 (3)	C6D—C2D—C10D—C9D	−52.1 (3)
S1B—C2B—C10B—C9B	−69.4 (2)	S1D—C2D—C10D—C9D	70.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5B—H5B···O3A^i	0.94	2.39	3.263 (4)	155
C5A—H5A···O3B^ii	0.94	2.49	3.376 (4)	158
C5D—H5D···O3C^i	0.94	2.40	3.248 (4)	151
C5C—H5C···O3D^ii	0.94	2.54	3.380 (4)	150

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