(S)-4,5-Diphenyl-1-[1-phenyl-3-(phenyl-sulfan-yl)propan-2-yl]-2-(thio-phen-2-yl)-1H-imidazole.

In the title compound, C34H28N2S2, the central imidazole ring (r.m.s. deviation = 0.0015 Å) forms dihedral angles of 55.7 (3), 17.94 (11) and 86.27 (11)°, respectively, with the mean planes of the attached thienyl and two phenyl substituents. The thienyl ring shows ring-flip disorder [occupancy ratio = 0.647 (2):0.353 (2)]. The chiral centre maintains the S configuration of the l-phenyl-alaninol starting material. Intra- and inter-molecular C-H⋯S hydrogen bonds involving the disordered thienyl ring are observed.

Related literature

For the synthesis of aryl sulfides, see: Mispelaere-Canivet et al. (2005 ▶); Zhang et al. (2007 ▶); Wu et al. (2009 ▶); Lv & Bao (2007 ▶). For related compounds synthesized by our group, see: Mao et al. (2010 ▶); Yang et al. (2012 ▶); Xiao et al. (2012 ▶); Gao et al. (2013 ▶).

Experimental

Crystal data

C34H28N2S2

M = 528.70

Orthorhombic,

a = 12.7882 (7) Å

b = 13.7906 (6) Å

c = 16.0636 (7) Å

V = 2832.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 1.89 mm−1

T = 291 K

0.26 × 0.23 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan CrysAlis PRO; Agilent, 2011 ▶ T min = 0.906, T max = 1.000

10599 measured reflections

5065 independent reflections

4456 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.03

5065 reflections

356 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 2202 Friedel pairs

Absolute structure parameter: 0.00 (2)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536813032066/rz5094sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032066/rz5094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813032066/rz5094Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C34H28N2S2	Dx = 1.240 Mg m−3
Mr = 528.70	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121	Cell parameters from 4362 reflections
a = 12.7882 (7) Å	θ = 5.4–72.0°
b = 13.7906 (6) Å	µ = 1.89 mm−1
c = 16.0636 (7) Å	T = 291 K
V = 2832.9 (2) Å3	Prism, colourless
Z = 4	0.26 × 0.23 × 0.2 mm
F(000) = 1112

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	5065 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4456 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 16.2312 pixels mm-1	θmax = 67.1°, θmin = 4.2°
ω scans	h = −15→14
Absorption correction: multi-scan CrysAlis PRO; Agilent, 2011	k = −16→16
Tmin = 0.906, Tmax = 1.000	l = −19→13
10599 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.3647P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5065 reflections	Δρmax = 0.19 e Å−3
356 parameters	Δρmin = −0.17 e Å−3
18 restraints	Absolute structure: Flack (1983), 2202 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.81367 (14)	0.86015 (13)	0.18676 (10)	0.0729 (4)	0.647 (2)
S1A	1.0259 (4)	0.8013 (3)	0.1389 (3)	0.0729 (4)	0.353 (2)
S2	0.81179 (9)	0.59192 (7)	0.34985 (7)	0.1012 (3)
N1	0.94171 (17)	0.89681 (13)	0.35239 (13)	0.0577 (5)
N2	0.99498 (16)	0.74395 (13)	0.34692 (13)	0.0580 (5)
C1	0.9468 (3)	1.0322 (2)	0.48649 (18)	0.0746 (7)
H1	0.9486	1.0543	0.4318	0.089*
C2	0.9363 (3)	1.0980 (2)	0.5507 (2)	0.0894 (10)
H2	0.9311	1.1639	0.5388	0.107*
C3	0.9334 (3)	1.0675 (3)	0.6313 (2)	0.0899 (10)
H3	0.9279	1.1123	0.6743	0.108*
C4	0.9387 (4)	0.9715 (3)	0.6481 (2)	0.1072 (13)
H4	0.9358	0.9504	0.7030	0.129*
C5	0.9485 (4)	0.9043 (3)	0.5844 (2)	0.0957 (11)
H5	0.9510	0.8384	0.5969	0.115*
C6	0.9547 (2)	0.9346 (2)	0.50214 (16)	0.0636 (6)
C7	0.9663 (2)	0.86640 (18)	0.43152 (15)	0.0586 (5)
C8	0.9998 (2)	0.77216 (18)	0.43000 (16)	0.0581 (5)
C9	1.0384 (2)	0.70951 (18)	0.49927 (17)	0.0636 (6)
C10	1.1412 (3)	0.7148 (3)	0.5238 (2)	0.0880 (10)
H10	1.1864	0.7573	0.4969	0.106*
C11	1.1781 (3)	0.6576 (4)	0.5881 (2)	0.1129 (15)
H11	1.2481	0.6608	0.6035	0.136*
C12	1.1111 (5)	0.5961 (3)	0.6291 (3)	0.1145 (15)
H12	1.1359	0.5573	0.6722	0.137*
C13	1.0084 (4)	0.5919 (3)	0.6068 (3)	0.1089 (14)
H13	0.9630	0.5510	0.6352	0.131*
C14	0.9716 (3)	0.6484 (2)	0.5419 (2)	0.0862 (9)
H14	0.9014	0.6452	0.5270	0.103*
C15	1.2350 (3)	0.7748 (3)	0.2846 (2)	0.0915 (10)
H15	1.2166	0.7990	0.3366	0.110*
C16	1.2929 (4)	0.8319 (5)	0.2318 (3)	0.1296 (17)
H16	1.3138	0.8938	0.2476	0.156*
C17	1.3196 (5)	0.7947 (6)	0.1542 (4)	0.162 (2)
H17	1.3566	0.8323	0.1162	0.195*
C18	1.2909 (5)	0.7026 (6)	0.1346 (4)	0.171 (3)
H18	1.3122	0.6768	0.0839	0.205*
C19	1.2322 (4)	0.6470 (5)	0.1861 (3)	0.140 (2)
H19	1.2117	0.5852	0.1698	0.169*
C20	1.2032 (2)	0.6824 (3)	0.2626 (2)	0.0829 (9)
C21	1.1339 (3)	0.6223 (2)	0.3168 (3)	0.0912 (10)
H21A	1.1560	0.6298	0.3742	0.109*
H21B	1.1426	0.5546	0.3019	0.109*
C22	1.0172 (2)	0.64862 (18)	0.3103 (2)	0.0718 (7)
H22	1.0012	0.6537	0.2508	0.086*
C23	0.9491 (3)	0.5675 (2)	0.3445 (2)	0.0892 (9)
H23A	0.9734	0.5518	0.4001	0.107*
H23B	0.9594	0.5105	0.3101	0.107*
C24	0.7696 (3)	0.5971 (2)	0.2451 (3)	0.0890 (9)
C25	0.8234 (3)	0.5596 (3)	0.1775 (3)	0.1055 (11)
H25	0.8884	0.5308	0.1856	0.127*
C26	0.7819 (4)	0.5644 (4)	0.0983 (3)	0.1259 (17)
H26	0.8187	0.5382	0.0538	0.151*
C27	0.6879 (4)	0.6071 (4)	0.0850 (4)	0.1328 (17)
H27	0.6607	0.6113	0.0314	0.159*
C28	0.6332 (4)	0.6443 (4)	0.1515 (4)	0.1305 (17)
H28	0.5681	0.6727	0.1429	0.157*
C29	0.6739 (3)	0.6397 (3)	0.2305 (3)	0.1080 (13)
H29	0.6364	0.6658	0.2748	0.130*
C30	0.9593 (2)	0.82233 (16)	0.30391 (15)	0.0548 (5)
C31	0.9363 (2)	0.82435 (16)	0.21422 (16)	0.0590 (6)
C32	0.9968 (7)	0.8110 (9)	0.1418 (7)	0.108 (4)	0.647 (2)
H32	1.0664	0.7912	0.1424	0.130*	0.647 (2)
C32A	0.8446 (13)	0.8515 (15)	0.1757 (10)	0.108 (4)	0.353 (2)
H32A	0.7844	0.8649	0.2060	0.130*	0.353 (2)
C33	0.9421 (13)	0.8304 (11)	0.0703 (5)	0.099 (3)	0.647 (2)
H33	0.9687	0.8242	0.0167	0.118*	0.647 (2)
C33A	0.847 (3)	0.858 (3)	0.0864 (10)	0.099 (3)	0.353 (2)
H33A	0.7910	0.8752	0.0520	0.118*	0.353 (2)
C34	0.8463 (12)	0.8591 (13)	0.0882 (7)	0.094 (3)	0.647 (2)
H34	0.7996	0.8778	0.0469	0.113*	0.647 (2)
C34A	0.946 (2)	0.835 (2)	0.0614 (14)	0.094 (3)	0.353 (2)
H34A	0.9678	0.8376	0.0061	0.113*	0.353 (2)

	U11	U22	U33	U12	U13	U23
S1	0.0778 (9)	0.0781 (7)	0.0629 (6)	0.0021 (6)	−0.0096 (5)	0.0013 (5)
S1A	0.0778 (9)	0.0781 (7)	0.0629 (6)	0.0021 (6)	−0.0096 (5)	0.0013 (5)
S2	0.1050 (6)	0.0971 (6)	0.1016 (6)	−0.0232 (5)	0.0174 (5)	−0.0074 (5)
N1	0.0672 (12)	0.0472 (9)	0.0586 (11)	0.0048 (9)	−0.0024 (10)	−0.0020 (8)
N2	0.0631 (11)	0.0494 (9)	0.0614 (11)	0.0049 (8)	−0.0007 (9)	0.0001 (9)
C1	0.092 (2)	0.0657 (15)	0.0662 (16)	0.0033 (15)	0.0043 (15)	−0.0062 (12)
C2	0.111 (3)	0.0676 (16)	0.090 (2)	0.0007 (18)	0.0077 (19)	−0.0194 (16)
C3	0.095 (2)	0.093 (2)	0.081 (2)	0.0054 (18)	0.0012 (18)	−0.0309 (17)
C4	0.143 (4)	0.122 (3)	0.0566 (17)	0.029 (3)	0.003 (2)	−0.0110 (19)
C5	0.138 (3)	0.084 (2)	0.0645 (17)	0.020 (2)	0.0056 (19)	−0.0057 (15)
C6	0.0631 (14)	0.0697 (14)	0.0579 (13)	0.0050 (12)	−0.0044 (12)	−0.0070 (11)
C7	0.0614 (13)	0.0564 (12)	0.0581 (13)	0.0033 (11)	−0.0056 (10)	0.0021 (10)
C8	0.0581 (13)	0.0563 (12)	0.0599 (13)	0.0021 (10)	−0.0029 (11)	0.0039 (10)
C9	0.0706 (15)	0.0593 (12)	0.0610 (13)	0.0089 (12)	−0.0025 (12)	0.0053 (11)
C10	0.0692 (18)	0.118 (3)	0.0768 (19)	0.0072 (18)	−0.0058 (15)	0.0165 (18)
C11	0.093 (3)	0.166 (4)	0.079 (2)	0.047 (3)	−0.017 (2)	0.013 (3)
C12	0.160 (4)	0.102 (3)	0.081 (2)	0.044 (3)	−0.015 (3)	0.023 (2)
C13	0.154 (4)	0.088 (2)	0.085 (2)	−0.009 (3)	0.003 (2)	0.0303 (19)
C14	0.089 (2)	0.0846 (19)	0.085 (2)	−0.0069 (17)	−0.0022 (17)	0.0202 (17)
C15	0.091 (2)	0.103 (2)	0.080 (2)	0.0019 (19)	−0.0002 (17)	−0.0148 (19)
C16	0.088 (3)	0.172 (5)	0.129 (4)	−0.022 (3)	0.003 (3)	0.021 (4)
C17	0.109 (3)	0.236 (6)	0.143 (4)	−0.015 (4)	0.045 (3)	0.031 (4)
C18	0.142 (4)	0.264 (6)	0.107 (3)	0.017 (5)	0.051 (3)	−0.032 (4)
C19	0.096 (3)	0.216 (6)	0.110 (3)	0.022 (3)	0.008 (2)	−0.085 (4)
C20	0.0703 (18)	0.102 (2)	0.0767 (18)	0.0235 (16)	−0.0040 (14)	−0.0269 (17)
C21	0.092 (2)	0.0697 (18)	0.112 (3)	0.0286 (16)	−0.003 (2)	−0.0105 (18)
C22	0.0861 (19)	0.0494 (12)	0.0799 (17)	0.0094 (12)	−0.0020 (14)	−0.0054 (12)
C23	0.114 (3)	0.0509 (13)	0.103 (2)	−0.0030 (15)	−0.006 (2)	0.0003 (15)
C24	0.080 (2)	0.0751 (18)	0.111 (3)	−0.0192 (16)	0.0114 (19)	−0.0018 (18)
C25	0.082 (2)	0.122 (3)	0.112 (3)	−0.007 (2)	0.008 (2)	−0.002 (2)
C26	0.109 (3)	0.170 (5)	0.099 (3)	−0.032 (3)	0.005 (3)	−0.002 (3)
C27	0.107 (3)	0.159 (5)	0.132 (4)	−0.035 (4)	−0.015 (3)	0.024 (4)
C28	0.100 (3)	0.120 (4)	0.171 (5)	−0.012 (3)	−0.025 (4)	0.008 (4)
C29	0.094 (3)	0.084 (2)	0.146 (4)	−0.012 (2)	0.004 (3)	−0.008 (2)
C30	0.0603 (13)	0.0486 (11)	0.0556 (12)	0.0022 (10)	−0.0015 (10)	−0.0009 (9)
C31	0.0662 (15)	0.0494 (11)	0.0615 (13)	−0.0035 (11)	−0.0043 (11)	−0.0035 (10)
C32	0.097 (7)	0.131 (7)	0.096 (5)	0.002 (5)	−0.012 (5)	−0.023 (4)
C32A	0.097 (7)	0.131 (7)	0.096 (5)	0.002 (5)	−0.012 (5)	−0.023 (4)
C33	0.125 (7)	0.127 (7)	0.044 (3)	−0.004 (5)	0.015 (3)	−0.024 (4)
C33A	0.125 (7)	0.127 (7)	0.044 (3)	−0.004 (5)	0.015 (3)	−0.024 (4)
C34	0.087 (5)	0.112 (6)	0.084 (4)	−0.001 (4)	−0.033 (4)	0.003 (4)
C34A	0.087 (5)	0.112 (6)	0.084 (4)	−0.001 (4)	−0.033 (4)	0.003 (4)

S1—C31	1.702 (3)	C16—C17	1.391 (8)
S1—C34	1.637 (12)	C17—H17	0.9300
S1A—C31	1.696 (5)	C17—C18	1.359 (9)
S1A—C34A	1.673 (18)	C18—H18	0.9300
S2—C23	1.789 (4)	C18—C19	1.355 (9)
S2—C24	1.769 (4)	C19—H19	0.9300
N1—C7	1.375 (3)	C19—C20	1.373 (5)
N1—C30	1.308 (3)	C20—C21	1.493 (5)
N2—C8	1.392 (3)	C21—H21A	0.9700
N2—C22	1.468 (3)	C21—H21B	0.9700
N2—C30	1.361 (3)	C21—C22	1.539 (4)
C1—H1	0.9300	C22—H22	0.9800
C1—C2	1.381 (4)	C22—C23	1.521 (4)
C1—C6	1.373 (4)	C23—H23A	0.9700
C2—H2	0.9300	C23—H23B	0.9700
C2—C3	1.361 (5)	C24—C25	1.386 (5)
C3—H3	0.9300	C24—C29	1.377 (6)
C3—C4	1.353 (5)	C25—H25	0.9300
C4—H4	0.9300	C25—C26	1.379 (6)
C4—C5	1.386 (5)	C26—H26	0.9300
C5—H5	0.9300	C26—C27	1.355 (8)
C5—C6	1.388 (4)	C27—H27	0.9300
C6—C7	1.481 (3)	C27—C28	1.376 (7)
C7—C8	1.369 (4)	C28—H28	0.9300
C8—C9	1.493 (3)	C28—C29	1.374 (7)
C9—C10	1.374 (4)	C29—H29	0.9300
C9—C14	1.382 (4)	C30—C31	1.471 (3)
C10—H10	0.9300	C31—C32	1.410 (11)
C10—C11	1.383 (5)	C31—C32A	1.377 (16)
C11—H11	0.9300	C32—H32	0.9300
C11—C12	1.373 (6)	C32—C33	1.371 (11)
C12—H12	0.9300	C32A—H32A	0.9300
C12—C13	1.363 (7)	C32A—C33A	1.438 (18)
C13—H13	0.9300	C33—H33	0.9300
C13—C14	1.383 (5)	C33—C34	1.318 (12)
C14—H14	0.9300	C33A—H33A	0.9300
C15—H15	0.9300	C33A—C34A	1.375 (18)
C15—C16	1.374 (6)	C34—H34	0.9300
C15—C20	1.383 (5)	C34A—H34A	0.9300
C16—H16	0.9300
C34—S1—C31	90.7 (5)	C19—C20—C21	119.0 (4)
C34A—S1A—C31	93.9 (10)	C20—C21—H21A	108.8
C24—S2—C23	105.15 (18)	C20—C21—H21B	108.8
C30—N1—C7	105.8 (2)	C20—C21—C22	113.9 (3)
C8—N2—C22	128.8 (2)	H21A—C21—H21B	107.7
C30—N2—C8	106.22 (19)	C22—C21—H21A	108.8
C30—N2—C22	124.9 (2)	C22—C21—H21B	108.8
C2—C1—H1	119.5	N2—C22—C21	111.8 (2)
C6—C1—H1	119.5	N2—C22—H22	106.6
C6—C1—C2	121.0 (3)	N2—C22—C23	113.7 (3)
C1—C2—H2	119.7	C21—C22—H22	106.6
C3—C2—C1	120.6 (3)	C23—C22—C21	111.0 (3)
C3—C2—H2	119.7	C23—C22—H22	106.6
C2—C3—H3	120.3	S2—C23—H23A	108.2
C4—C3—C2	119.4 (3)	S2—C23—H23B	108.2
C4—C3—H3	120.3	C22—C23—S2	116.2 (2)
C3—C4—H4	119.6	C22—C23—H23A	108.2
C3—C4—C5	120.8 (3)	C22—C23—H23B	108.2
C5—C4—H4	119.6	H23A—C23—H23B	107.4
C4—C5—H5	119.8	C25—C24—S2	125.4 (3)
C4—C5—C6	120.4 (3)	C29—C24—S2	116.7 (3)
C6—C5—H5	119.8	C29—C24—C25	117.9 (4)
C1—C6—C5	117.7 (3)	C24—C25—H25	119.6
C1—C6—C7	119.3 (2)	C26—C25—C24	120.9 (4)
C5—C6—C7	122.9 (3)	C26—C25—H25	119.6
N1—C7—C6	119.5 (2)	C25—C26—H26	119.7
C8—C7—N1	110.2 (2)	C27—C26—C25	120.6 (5)
C8—C7—C6	130.4 (2)	C27—C26—H26	119.7
N2—C8—C9	124.6 (2)	C26—C27—H27	120.4
C7—C8—N2	105.6 (2)	C26—C27—C28	119.3 (5)
C7—C8—C9	129.8 (2)	C28—C27—H27	120.4
C10—C9—C8	120.0 (3)	C27—C28—H28	119.7
C10—C9—C14	118.8 (3)	C29—C28—C27	120.5 (5)
C14—C9—C8	121.2 (3)	C29—C28—H28	119.7
C9—C10—H10	119.6	C24—C29—H29	119.6
C9—C10—C11	120.7 (4)	C28—C29—C24	120.9 (5)
C11—C10—H10	119.6	C28—C29—H29	119.6
C10—C11—H11	120.1	N1—C30—N2	112.3 (2)
C12—C11—C10	119.8 (4)	N1—C30—C31	122.2 (2)
C12—C11—H11	120.1	N2—C30—C31	125.4 (2)
C11—C12—H12	120.0	S1A—C31—S1	119.4 (2)
C13—C12—C11	120.1 (3)	C30—C31—S1	116.4 (2)
C13—C12—H12	120.0	C30—C31—S1A	124.1 (2)
C12—C13—H13	119.9	C32—C31—S1	109.3 (4)
C12—C13—C14	120.2 (4)	C32—C31—C30	134.1 (5)
C14—C13—H13	119.9	C32A—C31—S1A	107.8 (7)
C9—C14—C13	120.4 (4)	C32A—C31—C30	128.0 (7)
C9—C14—H14	119.8	C32A—C31—C32	97.6 (7)
C13—C14—H14	119.8	C31—C32—H32	123.7
C16—C15—H15	119.0	C33—C32—C31	112.6 (8)
C16—C15—C20	121.9 (4)	C33—C32—H32	123.7
C20—C15—H15	119.0	C31—C32A—H32A	121.6
C15—C16—H16	120.8	C31—C32A—C33A	116.8 (17)
C15—C16—C17	118.3 (6)	C33A—C32A—H32A	121.6
C17—C16—H16	120.8	C32—C33—H33	124.8
C16—C17—H17	120.5	C34—C33—C32	110.5 (9)
C18—C17—C16	119.1 (6)	C34—C33—H33	124.8
C18—C17—H17	120.5	C32A—C33A—H33A	126.5
C17—C18—H18	118.8	C34A—C33A—C32A	107 (2)
C19—C18—C17	122.5 (6)	C34A—C33A—H33A	126.5
C19—C18—H18	118.8	S1—C34—H34	121.6
C18—C19—H19	120.1	C33—C34—S1	116.8 (8)
C18—C19—C20	119.7 (6)	C33—C34—H34	121.6
C20—C19—H19	120.1	S1A—C34A—H34A	122.9
C15—C20—C21	122.5 (3)	C33A—C34A—S1A	114 (2)
C19—C20—C15	118.4 (4)	C33A—C34A—H34A	122.9
S1—C31—C32—C33	0.3 (12)	C15—C20—C21—C22	80.1 (4)
S1—C31—C32A—C33A	177 (6)	C16—C15—C20—C19	1.0 (6)
S1A—C31—C32—C33	176 (4)	C16—C15—C20—C21	−175.5 (4)
S1A—C31—C32A—C33A	−3 (2)	C16—C17—C18—C19	3.6 (12)
S2—C24—C25—C26	177.7 (4)	C17—C18—C19—C20	−2.5 (11)
S2—C24—C29—C28	−177.9 (3)	C18—C19—C20—C15	0.1 (7)
N1—C7—C8—N2	−0.3 (3)	C18—C19—C20—C21	176.8 (5)
N1—C7—C8—C9	177.5 (3)	C19—C20—C21—C22	−96.4 (4)
N1—C30—C31—S1	−51.8 (3)	C20—C15—C16—C17	0.1 (7)
N1—C30—C31—S1A	123.7 (3)	C20—C21—C22—N2	−69.4 (4)
N1—C30—C31—C32	121.4 (7)	C20—C21—C22—C23	162.5 (3)
N1—C30—C31—C32A	−50.8 (12)	C21—C22—C23—S2	174.6 (2)
N2—C8—C9—C10	93.9 (4)	C22—N2—C8—C7	−176.8 (3)
N2—C8—C9—C14	−88.7 (4)	C22—N2—C8—C9	5.3 (4)
N2—C22—C23—S2	47.4 (4)	C22—N2—C30—N1	177.2 (2)
N2—C30—C31—S1	124.4 (2)	C22—N2—C30—C31	0.6 (4)
N2—C30—C31—S1A	−60.1 (4)	C23—S2—C24—C25	18.5 (4)
N2—C30—C31—C32	−62.3 (8)	C23—S2—C24—C29	−163.3 (3)
N2—C30—C31—C32A	125.4 (12)	C24—S2—C23—C22	68.8 (3)
C1—C2—C3—C4	−1.4 (7)	C24—C25—C26—C27	0.8 (8)
C1—C6—C7—N1	−17.1 (4)	C25—C24—C29—C28	0.4 (6)
C1—C6—C7—C8	162.5 (3)	C25—C26—C27—C28	−1.1 (8)
C2—C1—C6—C5	1.9 (5)	C26—C27—C28—C29	1.1 (8)
C2—C1—C6—C7	−179.8 (3)	C27—C28—C29—C24	−0.8 (7)
C2—C3—C4—C5	0.9 (7)	C29—C24—C25—C26	−0.5 (6)
C3—C4—C5—C6	1.0 (7)	C30—N1—C7—C6	−180.0 (2)
C4—C5—C6—C1	−2.4 (6)	C30—N1—C7—C8	0.4 (3)
C4—C5—C6—C7	179.4 (4)	C30—N2—C8—C7	0.1 (3)
C5—C6—C7—N1	161.1 (3)	C30—N2—C8—C9	−177.8 (2)
C5—C6—C7—C8	−19.3 (5)	C30—N2—C22—C21	116.0 (3)
C6—C1—C2—C3	0.0 (6)	C30—N2—C22—C23	−117.3 (3)
C6—C7—C8—N2	−179.9 (3)	C30—C31—C32—C33	−173.3 (8)
C6—C7—C8—C9	−2.1 (5)	C30—C31—C32A—C33A	172.6 (18)
C7—N1—C30—N2	−0.3 (3)	C31—S1—C34—C33	2.5 (15)
C7—N1—C30—C31	176.3 (2)	C31—S1A—C34A—C33A	−5 (3)
C7—C8—C9—C10	−83.5 (4)	C31—C32—C33—C34	1.5 (18)
C7—C8—C9—C14	93.9 (4)	C31—C32A—C33A—C34A	0 (4)
C8—N2—C22—C21	−67.7 (4)	C32—C31—C32A—C33A	−2 (2)
C8—N2—C22—C23	59.0 (4)	C32—C33—C34—S1	−3 (2)
C8—N2—C30—N1	0.2 (3)	C32A—C31—C32—C33	0.5 (12)
C8—N2—C30—C31	−176.4 (2)	C32A—C33A—C34A—S1A	4 (3)
C8—C9—C10—C11	179.7 (3)	C34—S1—C31—S1A	−2.3 (7)
C8—C9—C14—C13	−179.0 (3)	C34—S1—C31—C30	173.4 (7)
C9—C10—C11—C12	−1.3 (6)	C34—S1—C31—C32	−1.4 (9)
C10—C9—C14—C13	−1.6 (5)	C34—S1—C31—C32A	−3 (5)
C10—C11—C12—C13	−0.4 (7)	C34A—S1A—C31—S1	3.8 (11)
C11—C12—C13—C14	1.0 (7)	C34A—S1A—C31—C30	−171.5 (10)
C12—C13—C14—C9	0.0 (6)	C34A—S1A—C31—C32	−1 (4)
C14—C9—C10—C11	2.2 (5)	C34A—S1A—C31—C32A	3.9 (15)
C15—C16—C17—C18	−2.3 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···S1i	0.97	2.75	3.677 (3)	161
C22—H22···S1A	0.98	2.73	3.468 (5)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯S1i	0.97	2.75	3.677 (3)	161
C22—H22⋯S1A	0.98	2.73	3.468 (5)	132

Symmetry code: (i) .