Crystal structure of 1,3-bis­{[4-(acetyl­sulfanyl)phenyl]ethynyl}azulene

Förster, S.; Seichter, W.; Weber, E.

doi:10.1107/S2056989016000323

organic compounds

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Volume 71| Part 12| December 2015| Pages o1099-o1100

https://doi.org/10.1107/S2056989016000323

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Crystal structure of 1,3-bis{[4-(acetylsulfanyl)phenyl]ethynyl}azulene

Sebastian Förster,^a Wilhelm Seichter ^a and Edwin Weber ^a ^*

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse, 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 November 2015; accepted 7 January 2016; online 31 December 2015)

In the title compound, C₃₀H₂₀O₂S₂, the dihedral angles between the central azulene ring system (r.m.s. deviation = 0.039 Å) and the pendant benzene rings are 28.96 (7) and 55.15 (7)°. The dihedral angles between the benzene rings and their attached acetylsulfanyl groups are 59.60 (10) and 84.79 (10)°. The expected π–π stacking interactions are not observed in the crystal structure; instead, the packing features C—H⋯O hydrogen bonds, which link the molecules into C(12) [010] chains, which are supported by weak C—H⋯π contacts.

Keywords: crystal structure; azulene; 1,3-disubstitution; C—H⋯O hydrogen bond; C—H⋯π interaction.

CCDC reference: 1445850

1. Related literature

For background to this work, see: Wang et al. (2009 ); Puodziukynaite et al. (2014 ); Xia et al. (2014 ). For the synthesis and related structures, see: Förster et al. (2012 , 2014 ).

2. Experimental

2.1. Crystal data

C₃₀H₂₀O₂S₂
M_r = 476.58
Monoclinic, P 2₁ /n
a = 13.7674 (3) Å
b = 8.9849 (2) Å
c = 19.7586 (4) Å
β = 104.022 (1)°
V = 2371.28 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.24 × 0.23 × 0.15 mm

2.2. Data collection

Bruker Kappa APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.942, T_max = 0.963
36340 measured reflections
5898 independent reflections
4422 reflections with I > 2σ(I)
R_int = 0.039

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.130
S = 1.03
5898 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the mid-point of the C11—C12 bond and Cg2 is the centroid of the C1–C4/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.40	3.285 (3)	155
C17—H1⋯Cg1	0.95	2.69	3.612 (3)	165
C20—H20A⋯Cg2ⁱⁱ	0.98	2.89	3.835 (2)	162
Symmetry code: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker AXS); cell refinement: SAINT (Sheldrick, 2008 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1445850

Crystal structure: contains datablocks I, publication_text. DOI: https://doi.org/10.1107/S2056989016000323/hb7546sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016000323/hb7546Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016000323/hb7546Isup3.cml

checkCIF report

Comment top

Azulene derivatives offer a number of interesting applications especially in the field of molecular electronics (Wang et al., 2009; Puodziukynaite et al., 2014). It ties up with the fact that the non-alternating azulene possesses remarkable electronic and optical properties (Xia et al., 2014). Although the title compound, C₃₀H₂₀O₂S₂, (I), is fully conjugated, no flat molecular structure can be observed. Both phenyl rings, fig 1, are rotated out of the plane containing the azulene core [phenyl(C13—C18) 29.0°, phenyl(C23—C28) 55.2°]. The C—S—C angle of the acetyl protected thiol is slightly smaller compared to that found in an analogous compound,1,3-bis[4-(tert-butylsulfanyl)phenylethynyl]azulene, featuring a tert-butyl protection group at the sulfur atom (Förster et al., 2012). Unlike the previous case, no π···π interactions are present in the title compound. In all probability, this uncommon phenomenon within the substance class of azulenes (Förster et al., 2014) is related to the non-planar molecular structure and may be caused from packing effects. However, the crystal structure is based on C—H···O hydrogen bonds [C2—-H2···O1 (2.5-x, -0.5+y, 1.5-z; 2.40 Å, 155.0°)] and C—H···π interactions [C17—H17···Cg(1) 2.69 Å, 164.9°; C20—H20A···Cg(2) 2.89 Å, 159.0°].

Experimental top

Synthesis and crystallization top

The synthesis of the title compound, (I), has already been described (Förster et al. 2012). The crystals were grown from toluene solution by slow evaporation.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The hydrogen atoms attached to C were fixed geometrically and treated as riding atoms, with d(C—H) = 0.93 and Uiso(H) = 1.2 Ueq(C) for aromatic and Uiso(H) = 1.5Ueq(C) for methyl groups.

Related literature top

For background to this work, see: Wang et al. (2009);, Puodziukynaite et al. (2014); Xia et al. (2014). For the synthesis and related structures, see: Förster et al. (2012, 2014).

Structure description top

For background to this work, see: Wang et al. (2009);, Puodziukynaite et al. (2014); Xia et al. (2014). For the synthesis and related structures, see: Förster et al. (2012, 2014).

Synthesis and crystallization top

The synthesis of the title compound, (I), has already been described (Förster et al. 2012). The crystals were grown from toluene solution by slow evaporation.

Refinement details top

Computing details top

Data collection: APEX2 (Bruker AXS); cell refinement: SAINT (Sheldrick, 2008); data reduction: SAINT (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Ellipsoid plot.
	Fig. 2. Packing diagram.

1,3-Bis{[4-(acetylsulfanyl)phenyl]ethynyl}azulene top

Crystal data top

C₃₀H₂₀O₂S₂	F(000) = 992
M_r = 476.58	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.7674 (3) Å	Cell parameters from 8057 reflections
b = 8.9849 (2) Å	θ = 2.5–28.0°
c = 19.7586 (4) Å	µ = 0.25 mm⁻¹
β = 104.022 (1)°	T = 100 K
V = 2371.28 (9) Å³	Irregular, green
Z = 4	0.24 × 0.23 × 0.15 mm

Data collection top

Bruker Kappa APEX CCD diffractometer	4422 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 28.3°, θ_min = 2.5°
T_min = 0.942, T_max = 0.963	h = −18→18
36340 measured reflections	k = −12→11
5898 independent reflections	l = −26→26

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0658P)² + 1.347P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5898 reflections	Δρ_max = 0.44 e Å⁻³
309 parameters	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₃₀H₂₀O₂S₂	V = 2371.28 (9) Å³
M_r = 476.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.7674 (3) Å	µ = 0.25 mm⁻¹
b = 8.9849 (2) Å	T = 100 K
c = 19.7586 (4) Å	0.24 × 0.23 × 0.15 mm
β = 104.022 (1)°

Data collection top

Bruker Kappa APEX CCD diffractometer	5898 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4422 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.963	R_int = 0.039
36340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
5898 reflections	Δρ_min = −0.27 e Å⁻³
309 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.37569 (4)	0.11544 (6)	0.58441 (3)	0.03405 (15)
S2	0.55913 (4)	−0.42293 (6)	1.10153 (3)	0.03144 (14)
O1	1.43557 (12)	0.39449 (19)	0.60090 (9)	0.0418 (4)
O2	0.52513 (12)	−0.17076 (16)	1.16136 (8)	0.0361 (4)
C1	0.93413 (13)	0.2985 (2)	0.81129 (9)	0.0229 (4)
C2	0.91025 (14)	0.1731 (2)	0.84616 (10)	0.0248 (4)
H2	0.9425	0.0791	0.8485	0.030*
C3	0.83172 (14)	0.2075 (2)	0.87699 (10)	0.0235 (4)
C4	0.80547 (13)	0.3585 (2)	0.86356 (9)	0.0224 (4)
C5	0.73471 (14)	0.4346 (2)	0.88954 (10)	0.0258 (4)
H5	0.7021	0.3782	0.9182	0.031*
C6	0.70505 (15)	0.5828 (2)	0.87924 (11)	0.0286 (4)
H6	0.6574	0.6156	0.9036	0.034*
C7	0.73635 (14)	0.6887 (2)	0.83792 (10)	0.0281 (4)
H7	0.7048	0.7831	0.8366	0.034*
C8	0.80679 (15)	0.6777 (2)	0.79820 (10)	0.0279 (4)
H8	0.8147	0.7643	0.7725	0.033*
C9	0.86748 (14)	0.5575 (2)	0.79079 (10)	0.0244 (4)
H9	0.9129	0.5744	0.7623	0.029*
C10	0.86986 (13)	0.4173 (2)	0.81964 (9)	0.0217 (4)
C11	1.01077 (14)	0.2995 (2)	0.77358 (10)	0.0235 (4)
C12	1.07506 (14)	0.2876 (2)	0.74377 (10)	0.0252 (4)
C13	1.15323 (13)	0.2606 (2)	0.70827 (10)	0.0222 (4)
C14	1.15694 (14)	0.3358 (2)	0.64730 (10)	0.0261 (4)
H14	1.1120	0.4155	0.6312	0.031*
C15	1.22577 (14)	0.2948 (2)	0.61000 (10)	0.0272 (4)
H15	1.2263	0.3440	0.5675	0.033*
C16	1.29404 (13)	0.1821 (2)	0.63447 (10)	0.0242 (4)
C17	1.29573 (14)	0.1142 (2)	0.69783 (10)	0.0270 (4)
H17	1.3454	0.0420	0.7163	0.032*
C18	1.22522 (14)	0.1517 (2)	0.73400 (10)	0.0269 (4)
H18	1.2256	0.1031	0.7768	0.032*
C19	1.44675 (15)	0.2760 (3)	0.57564 (11)	0.0328 (5)
C20	1.52157 (17)	0.2459 (3)	0.53316 (12)	0.0483 (7)
H20A	1.4865	0.2112	0.4866	0.072*
H20B	1.5688	0.1692	0.5562	0.072*
H20C	1.5582	0.3375	0.5289	0.072*
C21	0.78423 (15)	0.1054 (2)	0.91530 (9)	0.0243 (4)
C22	0.74797 (15)	0.0199 (2)	0.94649 (10)	0.0275 (4)
C23	0.70236 (14)	−0.0862 (2)	0.98362 (10)	0.0246 (4)
C24	0.76034 (15)	−0.1665 (2)	1.03950 (10)	0.0284 (4)
H24	0.8306	−0.1504	1.0535	0.034*
C25	0.71595 (15)	−0.2691 (2)	1.07442 (11)	0.0289 (4)
H25	0.7557	−0.3248	1.1119	0.035*
C26	0.61271 (15)	−0.2908 (2)	1.05464 (10)	0.0268 (4)
C27	0.55486 (15)	−0.2111 (2)	1.00026 (11)	0.0318 (5)
H27	0.4845	−0.2261	0.9870	0.038*
C28	0.59931 (15)	−0.1085 (2)	0.96468 (11)	0.0308 (4)
H28	0.5592	−0.0532	0.9272	0.037*
C29	0.52713 (14)	−0.3041 (2)	1.16535 (10)	0.0261 (4)
C30	0.50479 (17)	−0.3905 (2)	1.22472 (11)	0.0341 (5)
H30A	0.5636	−0.3895	1.2643	0.051*
H30B	0.4883	−0.4935	1.2100	0.051*
H30C	0.4479	−0.3451	1.2387	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0321 (3)	0.0331 (3)	0.0435 (3)	0.0021 (2)	0.0220 (2)	−0.0023 (2)
S2	0.0425 (3)	0.0203 (2)	0.0379 (3)	−0.0023 (2)	0.0221 (2)	0.0025 (2)
O1	0.0341 (8)	0.0477 (10)	0.0446 (9)	−0.0138 (7)	0.0117 (7)	−0.0013 (8)
O2	0.0478 (9)	0.0248 (8)	0.0381 (8)	0.0010 (7)	0.0152 (7)	0.0001 (6)
C1	0.0234 (9)	0.0222 (9)	0.0244 (9)	−0.0025 (7)	0.0085 (7)	−0.0004 (7)
C2	0.0276 (9)	0.0225 (9)	0.0260 (9)	−0.0003 (7)	0.0097 (7)	−0.0001 (8)
C3	0.0246 (9)	0.0238 (9)	0.0233 (9)	−0.0034 (7)	0.0083 (7)	0.0004 (7)
C4	0.0224 (8)	0.0239 (9)	0.0217 (9)	−0.0023 (7)	0.0069 (7)	−0.0007 (7)
C5	0.0232 (9)	0.0301 (10)	0.0266 (9)	−0.0025 (8)	0.0108 (7)	−0.0010 (8)
C6	0.0259 (9)	0.0312 (11)	0.0309 (10)	0.0015 (8)	0.0114 (8)	−0.0043 (8)
C7	0.0273 (9)	0.0266 (10)	0.0293 (10)	0.0039 (8)	0.0048 (8)	−0.0027 (8)
C8	0.0314 (10)	0.0241 (10)	0.0277 (10)	0.0006 (8)	0.0062 (8)	0.0041 (8)
C9	0.0259 (9)	0.0261 (10)	0.0224 (9)	−0.0024 (7)	0.0082 (7)	0.0002 (7)
C10	0.0208 (8)	0.0237 (9)	0.0213 (8)	−0.0023 (7)	0.0067 (7)	−0.0012 (7)
C11	0.0265 (9)	0.0180 (9)	0.0269 (9)	−0.0045 (7)	0.0083 (7)	−0.0018 (7)
C12	0.0272 (9)	0.0179 (9)	0.0309 (10)	−0.0011 (7)	0.0078 (8)	−0.0020 (7)
C13	0.0222 (8)	0.0193 (9)	0.0267 (9)	−0.0021 (7)	0.0093 (7)	−0.0034 (7)
C14	0.0234 (9)	0.0230 (10)	0.0331 (10)	0.0033 (7)	0.0093 (8)	0.0033 (8)
C15	0.0283 (9)	0.0271 (10)	0.0284 (10)	0.0010 (8)	0.0111 (8)	0.0059 (8)
C16	0.0217 (8)	0.0241 (10)	0.0293 (9)	−0.0010 (7)	0.0113 (7)	−0.0016 (8)
C17	0.0244 (9)	0.0240 (10)	0.0335 (10)	0.0033 (7)	0.0085 (8)	0.0027 (8)
C18	0.0293 (10)	0.0256 (10)	0.0279 (10)	0.0009 (8)	0.0108 (8)	0.0023 (8)
C19	0.0232 (9)	0.0482 (14)	0.0265 (10)	−0.0047 (9)	0.0051 (8)	0.0029 (9)
C20	0.0271 (11)	0.084 (2)	0.0374 (12)	−0.0038 (12)	0.0152 (9)	0.0081 (13)
C21	0.0329 (10)	0.0213 (9)	0.0204 (9)	0.0035 (8)	0.0095 (7)	−0.0006 (7)
C22	0.0301 (10)	0.0246 (10)	0.0304 (10)	0.0002 (8)	0.0126 (8)	−0.0050 (8)
C23	0.0321 (10)	0.0181 (9)	0.0284 (9)	−0.0015 (7)	0.0169 (8)	−0.0030 (7)
C24	0.0273 (9)	0.0285 (10)	0.0318 (10)	−0.0006 (8)	0.0115 (8)	0.0010 (8)
C25	0.0325 (10)	0.0262 (10)	0.0304 (10)	0.0028 (8)	0.0124 (8)	0.0046 (8)
C26	0.0357 (10)	0.0184 (9)	0.0314 (10)	−0.0013 (8)	0.0181 (8)	0.0002 (8)
C27	0.0253 (9)	0.0294 (11)	0.0424 (12)	−0.0021 (8)	0.0117 (8)	0.0057 (9)
C28	0.0309 (10)	0.0271 (10)	0.0358 (11)	0.0019 (8)	0.0110 (8)	0.0096 (9)
C29	0.0248 (9)	0.0233 (10)	0.0311 (10)	−0.0001 (7)	0.0085 (8)	0.0012 (8)
C30	0.0416 (12)	0.0305 (11)	0.0355 (11)	0.0012 (9)	0.0195 (9)	0.0028 (9)

Geometric parameters (Å, º) top

S1—C16	1.7716 (19)	C14—C15	1.384 (3)
S1—C19	1.775 (2)	C14—H14	0.9500
S2—C26	1.7727 (19)	C15—C16	1.387 (3)
S2—C29	1.787 (2)	C15—H15	0.9500
O1—C19	1.201 (3)	C16—C17	1.387 (3)
O2—C29	1.201 (2)	C17—C18	1.380 (3)
C1—C2	1.401 (3)	C17—H17	0.9500
C1—C10	1.421 (3)	C18—H18	0.9500
C1—C11	1.432 (2)	C19—C20	1.503 (3)
C2—C3	1.398 (3)	C20—H20A	0.9800
C2—H2	0.9500	C20—H20B	0.9800
C3—C4	1.413 (3)	C20—H20C	0.9800
C3—C21	1.443 (3)	C21—C22	1.170 (3)
C4—C5	1.386 (3)	C22—C23	1.437 (3)
C4—C10	1.480 (2)	C23—C28	1.391 (3)
C5—C6	1.393 (3)	C23—C24	1.396 (3)
C5—H5	0.9500	C24—C25	1.380 (3)
C6—C7	1.388 (3)	C24—H24	0.9500
C6—H6	0.9500	C25—C26	1.394 (3)
C7—C8	1.391 (3)	C25—H25	0.9500
C7—H7	0.9500	C26—C27	1.374 (3)
C8—C9	1.394 (3)	C27—C28	1.388 (3)
C8—H8	0.9500	C27—H27	0.9500
C9—C10	1.380 (3)	C28—H28	0.9500
C9—H9	0.9500	C29—C30	1.500 (3)
C11—C12	1.181 (3)	C30—H30A	0.9800
C12—C13	1.440 (3)	C30—H30B	0.9800
C13—C14	1.393 (3)	C30—H30C	0.9800
C13—C18	1.398 (3)

C16—S1—C19	102.66 (10)	C17—C16—S1	118.76 (15)
C26—S2—C29	100.01 (9)	C18—C17—C16	120.01 (18)
C2—C1—C10	108.67 (16)	C18—C17—H17	120.0
C2—C1—C11	123.48 (17)	C16—C17—H17	120.0
C10—C1—C11	127.85 (17)	C17—C18—C13	120.56 (18)
C3—C2—C1	109.57 (17)	C17—C18—H18	119.7
C3—C2—H2	125.2	C13—C18—H18	119.7
C1—C2—H2	125.2	O1—C19—C20	124.5 (2)
C2—C3—C4	108.68 (16)	O1—C19—S1	123.40 (16)
C2—C3—C21	125.77 (18)	C20—C19—S1	112.13 (18)
C4—C3—C21	125.55 (17)	C19—C20—H20A	109.5
C5—C4—C3	125.09 (17)	C19—C20—H20B	109.5
C5—C4—C10	128.00 (18)	H20A—C20—H20B	109.5
C3—C4—C10	106.88 (16)	C19—C20—H20C	109.5
C4—C5—C6	128.65 (18)	H20A—C20—H20C	109.5
C4—C5—H5	115.7	H20B—C20—H20C	109.5
C6—C5—H5	115.7	C22—C21—C3	178.1 (2)
C7—C6—C5	128.24 (18)	C21—C22—C23	178.9 (2)
C7—C6—H6	115.9	C28—C23—C24	119.25 (17)
C5—C6—H6	115.9	C28—C23—C22	120.10 (18)
C6—C7—C8	129.88 (19)	C24—C23—C22	120.64 (18)
C6—C7—H7	115.1	C25—C24—C23	120.20 (18)
C8—C7—H7	115.1	C25—C24—H24	119.9
C7—C8—C9	129.18 (19)	C23—C24—H24	119.9
C7—C8—H8	115.4	C24—C25—C26	119.92 (19)
C9—C8—H8	115.4	C24—C25—H25	120.0
C10—C9—C8	128.20 (18)	C26—C25—H25	120.0
C10—C9—H9	115.9	C27—C26—C25	120.30 (18)
C8—C9—H9	115.9	C27—C26—S2	121.48 (15)
C9—C10—C1	126.22 (17)	C25—C26—S2	118.21 (15)
C9—C10—C4	127.60 (17)	C26—C27—C28	119.96 (19)
C1—C10—C4	106.17 (16)	C26—C27—H27	120.0
C12—C11—C1	174.3 (2)	C28—C27—H27	120.0
C11—C12—C13	175.5 (2)	C27—C28—C23	120.36 (19)
C14—C13—C18	118.85 (17)	C27—C28—H28	119.8
C14—C13—C12	121.86 (17)	C23—C28—H28	119.8
C18—C13—C12	119.23 (17)	O2—C29—C30	124.21 (19)
C15—C14—C13	120.34 (18)	O2—C29—S2	123.75 (16)
C15—C14—H14	119.8	C30—C29—S2	112.03 (14)
C13—C14—H14	119.8	C29—C30—H30A	109.5
C14—C15—C16	120.16 (17)	C29—C30—H30B	109.5
C14—C15—H15	119.9	H30A—C30—H30B	109.5
C16—C15—H15	119.9	C29—C30—H30C	109.5
C15—C16—C17	119.82 (17)	H30A—C30—H30C	109.5
C15—C16—S1	121.35 (15)	H30B—C30—H30C	109.5

C10—C1—C2—C3	0.1 (2)	C13—C14—C15—C16	−2.4 (3)
C11—C1—C2—C3	−179.26 (17)	C14—C15—C16—C17	−2.5 (3)
C1—C2—C3—C4	−1.4 (2)	C14—C15—C16—S1	174.31 (15)
C1—C2—C3—C21	177.71 (18)	C19—S1—C16—C15	61.42 (18)
C2—C3—C4—C5	−175.89 (18)	C19—S1—C16—C17	−121.78 (17)
C21—C3—C4—C5	5.0 (3)	C15—C16—C17—C18	4.4 (3)
C2—C3—C4—C10	2.2 (2)	S1—C16—C17—C18	−172.40 (15)
C21—C3—C4—C10	−176.99 (17)	C16—C17—C18—C13	−1.6 (3)
C3—C4—C5—C6	179.6 (2)	C14—C13—C18—C17	−3.1 (3)
C10—C4—C5—C6	1.9 (3)	C12—C13—C18—C17	174.31 (18)
C4—C5—C6—C7	3.0 (4)	C16—S1—C19—O1	0.8 (2)
C5—C6—C7—C8	−2.4 (4)	C16—S1—C19—C20	−179.13 (15)
C6—C7—C8—C9	−2.1 (4)	C28—C23—C24—C25	1.4 (3)
C7—C8—C9—C10	2.4 (4)	C22—C23—C24—C25	−179.43 (18)
C8—C9—C10—C1	−179.16 (19)	C23—C24—C25—C26	−1.1 (3)
C8—C9—C10—C4	2.5 (3)	C24—C25—C26—C27	0.3 (3)
C2—C1—C10—C9	−177.39 (18)	C24—C25—C26—S2	−179.55 (15)
C11—C1—C10—C9	1.9 (3)	C29—S2—C26—C27	−86.86 (18)
C2—C1—C10—C4	1.2 (2)	C29—S2—C26—C25	92.98 (17)
C11—C1—C10—C4	−179.46 (18)	C25—C26—C27—C28	0.1 (3)
C5—C4—C10—C9	−5.5 (3)	S2—C26—C27—C28	179.98 (16)
C3—C4—C10—C9	176.53 (18)	C26—C27—C28—C23	0.2 (3)
C5—C4—C10—C1	175.89 (19)	C24—C23—C28—C27	−1.0 (3)
C3—C4—C10—C1	−2.1 (2)	C22—C23—C28—C27	179.86 (19)
C18—C13—C14—C15	5.1 (3)	C26—S2—C29—O2	14.4 (2)
C12—C13—C14—C15	−172.25 (18)	C26—S2—C29—C30	−164.72 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the mid-point of C11—C12 and Cg2 is the centroid of the C1–C4/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.40	3.285 (3)	155
C17—H1···Cg1	0.95	2.69	3.612 (3)	165
C20—H20A···Cg2ⁱⁱ	0.98	2.89	3.835 (2)	162

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) x+1/2, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the mid-point of C11—C12 and Cg2 is the centroid of the C1–C4/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.40	3.285 (3)	155
C17—H1···Cg1	0.95	2.69	3.612 (3)	164.9
C20—H20A···Cg2ⁱⁱ	0.98	2.89	3.835 (2)	162

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) x+1/2, −y+1/2, z−1/2.

Acknowledgements

This work has been performed within the `Cluster of Excellence Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering′ (ADDE), which was supported financially by the European Union (European Regional Development Fund) and by the Ministry of Science and Art of Saxony (SMWK).

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Volume 71| Part 12| December 2015| Pages o1099-o1100

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