(11aS)-1,5,11,11a-Tetra-hydro-1-benzo-thieno[3,2-f]indolizin-3(2H)-one.

The absolute configuration of the title compound, C14H13NOS, was assigned from the synthesis and confirmed by the structure determination. There are two independent mol-ecules in the asymmetric unit. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviations from the mean planes being 0.569 (3) and 0.561 (3) Å for the indolizine bridgehead C atoms of the two mol-ecules. The benzothieno ring attached to the indolizine ring system is planar to within 0.015 (3) Å in both mol-ecules. In the crystal, weak C-H⋯O and C-H⋯π inter-actions lead to the formation of a three-dimensional framework structure.

Related literature

For background to indolizine derivatives, see: Gubin et al. (1992 ▶); Gupta et al. (2003 ▶); Liu et al. (2007 ▶); Medda et al. (2003 ▶); Molyneux & James (1982 ▶); Nash et al. (1988 ▶); Pearson & Guo (2001 ▶); Ruprecht et al. (1989 ▶); Smith et al. (2007 ▶); Teklu et al. (2005 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the synthesis, see: Šafář et al. (2009 ▶). For a related structure, see: Vrábel et al. (2012 ▶).

Experimental

Crystal data

C14H13NOS

M = 243.31

Monoclinic,

a = 9.3327 (8) Å

b = 12.4575 (7) Å

c = 10.3103 (7) Å

β = 105.469 (8)°

V = 1155.27 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 295 K

0.30 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.942, T max = 0.969

17520 measured reflections

4061 independent reflections

2918 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.065

S = 0.94

4061 reflections

307 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 1923 Friedel pairs

Absolute structure parameter: −0.07 (6)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶), WinGX (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813031693/bq2390sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031693/bq2390Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031693/bq2390Isup3.cml

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

C14H13NOS	F(000) = 512
Mr = 243.31	Dx = 1.399 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3929 reflections
a = 9.3327 (8) Å	θ = 3.9–24.6°
b = 12.4575 (7) Å	µ = 0.26 mm−1
c = 10.3103 (7) Å	T = 295 K
β = 105.469 (8)°	Block, colourless
V = 1155.27 (14) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer	4061 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
Detector resolution: 10.4340 pixels mm-1	θmax = 25.0°, θmin = 3.8°
ω scans	h = −11→11
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009)	k = −14→14
Tmin = 0.942, Tmax = 0.969	l = −12→12
17520 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0158P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
4061 reflections	Δρmax = 0.19 e Å−3
307 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 1923 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (6)

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
C9	1.1545 (4)	0.5063 (2)	1.0070 (3)	0.0510 (9)
H9	1.1930	0.5751	1.0058	0.061*
C10	1.2105 (4)	0.4396 (3)	1.1129 (3)	0.0575 (9)
H10	1.2865	0.4632	1.1853	0.069*
C11	1.1545 (4)	0.3363 (3)	1.1131 (3)	0.0549 (9)
H11	1.1951	0.2907	1.1850	0.066*
C12	1.0399 (3)	0.3006 (2)	1.0084 (3)	0.0510 (8)
H12	1.0030	0.2314	1.0105	0.061*
C15	0.7720 (3)	0.2472 (2)	0.7527 (3)	0.0493 (8)
H15B	0.8362	0.1895	0.7391	0.059*
H15A	0.7339	0.2284	0.8286	0.059*
C2	0.5277 (4)	0.1948 (2)	0.6049 (3)	0.0460 (8)
C3	0.4370 (3)	0.2215 (2)	0.4647 (3)	0.0505 (8)
H3B	0.3350	0.2374	0.4640	0.061*
H3A	0.4372	0.1619	0.4042	0.061*
C4	0.5101 (4)	0.3191 (2)	0.4224 (3)	0.0560 (9)
H4B	0.4530	0.3834	0.4271	0.067*
H4A	0.5183	0.3109	0.3311	0.067*
C6	0.7111 (3)	0.4385 (2)	0.5692 (3)	0.0483 (8)
H6B	0.7476	0.4757	0.5018	0.058*
H6A	0.6266	0.4781	0.5826	0.058*
C8	1.0392 (3)	0.4704 (2)	0.9009 (3)	0.0402 (7)
C13	0.9791 (3)	0.36689 (19)	0.8999 (3)	0.0386 (7)
C7	0.8309 (3)	0.43324 (19)	0.6986 (3)	0.0410 (7)
C14	0.8593 (3)	0.3489 (2)	0.7827 (3)	0.0392 (7)
C5	0.6634 (3)	0.3257 (2)	0.5214 (3)	0.0443 (8)
H5	0.7373	0.2940	0.4808	0.053*
C23	0.0755 (3)	0.3963 (2)	0.4371 (3)	0.0459 (8)
H23	0.0459	0.4457	0.3675	0.055*
C24	0.0128 (3)	0.2967 (2)	0.4263 (3)	0.0490 (8)
H24	−0.0590	0.2776	0.3483	0.059*
C25	0.0553 (3)	0.2236 (2)	0.5311 (3)	0.0489 (8)
H25	0.0109	0.1562	0.5228	0.059*
C26	0.1622 (3)	0.2495 (2)	0.6473 (3)	0.0440 (8)
H26	0.1891	0.2003	0.7174	0.053*
C29	0.4260 (3)	0.3311 (2)	0.8896 (3)	0.0419 (7)
H29B	0.3558	0.3157	0.9416	0.050*
H29A	0.4627	0.2634	0.8649	0.050*
C16	0.6609 (4)	0.3507 (2)	1.0638 (3)	0.0497 (8)
C17	0.7553 (4)	0.4401 (2)	1.1378 (3)	0.0576 (9)
H17B	0.7465	0.4451	1.2292	0.069*
H17A	0.8589	0.4287	1.1406	0.069*
C18	0.6977 (4)	0.5393 (3)	1.0606 (3)	0.0731 (10)
H18B	0.7623	0.5611	1.0057	0.088*
H18A	0.6915	0.5976	1.1213	0.088*
C20	0.5094 (3)	0.5562 (2)	0.8317 (3)	0.0439 (7)
H20B	0.4790	0.6306	0.8323	0.053*
H20A	0.5974	0.5533	0.7987	0.053*
C22	0.1835 (3)	0.42259 (19)	0.5527 (3)	0.0365 (7)
C27	0.2297 (3)	0.3498 (2)	0.6591 (2)	0.0338 (7)
C21	0.3872 (3)	0.4920 (2)	0.7414 (3)	0.0375 (7)
C28	0.3499 (3)	0.3920 (2)	0.7654 (2)	0.0338 (6)
C19	0.5440 (4)	0.51079 (19)	0.9726 (3)	0.0466 (8)
H19	0.4683	0.5343	1.0165	0.056*
N1	0.6489 (3)	0.25973 (16)	0.6329 (2)	0.0427 (6)
N2	0.5487 (3)	0.39360 (16)	0.9700 (2)	0.0430 (6)
O1	0.5026 (3)	0.12637 (15)	0.6797 (2)	0.0613 (6)
O2	0.6828 (3)	0.25454 (16)	1.0830 (2)	0.0706 (7)
S1	0.94828 (9)	0.54148 (6)	0.75781 (7)	0.0501 (2)
S2	0.28209 (8)	0.54190 (6)	0.58804 (7)	0.0476 (2)

	U11	U22	U33	U12	U13	U23
C9	0.044 (2)	0.0506 (19)	0.055 (2)	−0.0032 (15)	0.0087 (18)	−0.0123 (14)
C10	0.043 (2)	0.074 (2)	0.049 (2)	−0.0014 (19)	0.0014 (16)	−0.0114 (17)
C11	0.048 (2)	0.071 (2)	0.042 (2)	0.0015 (18)	0.0059 (17)	0.0063 (15)
C12	0.049 (2)	0.0541 (18)	0.0468 (19)	−0.0069 (16)	0.0081 (18)	0.0042 (14)
C15	0.048 (2)	0.0450 (17)	0.049 (2)	0.0015 (15)	0.0036 (17)	0.0027 (13)
C2	0.036 (2)	0.0430 (18)	0.057 (2)	0.0069 (15)	0.0098 (17)	−0.0096 (16)
C3	0.039 (2)	0.0594 (19)	0.050 (2)	0.0049 (16)	0.0052 (16)	−0.0099 (15)
C4	0.052 (2)	0.061 (2)	0.047 (2)	0.0021 (17)	0.0016 (17)	−0.0016 (15)
C6	0.055 (2)	0.0417 (16)	0.0427 (18)	0.0017 (15)	0.0038 (16)	0.0023 (13)
C8	0.040 (2)	0.0402 (17)	0.0414 (18)	0.0004 (14)	0.0134 (16)	−0.0031 (12)
C13	0.0358 (19)	0.0418 (17)	0.0387 (17)	0.0004 (13)	0.0112 (15)	−0.0003 (13)
C7	0.043 (2)	0.0371 (16)	0.0429 (18)	0.0020 (13)	0.0110 (15)	−0.0021 (13)
C14	0.043 (2)	0.0348 (15)	0.0384 (17)	−0.0012 (13)	0.0079 (15)	0.0008 (12)
C5	0.044 (2)	0.0455 (17)	0.0397 (18)	0.0064 (14)	0.0040 (15)	−0.0017 (13)
C23	0.035 (2)	0.0551 (19)	0.0393 (18)	0.0062 (15)	−0.0044 (15)	0.0019 (14)
C24	0.0348 (19)	0.064 (2)	0.0426 (19)	−0.0037 (16)	−0.0001 (15)	−0.0093 (15)
C25	0.039 (2)	0.0517 (18)	0.053 (2)	−0.0080 (15)	0.0067 (17)	−0.0070 (15)
C26	0.044 (2)	0.0436 (17)	0.0400 (18)	−0.0026 (14)	0.0039 (15)	0.0021 (13)
C29	0.041 (2)	0.0412 (16)	0.0375 (17)	−0.0023 (14)	0.0008 (15)	0.0007 (13)
C16	0.047 (2)	0.054 (2)	0.043 (2)	−0.0011 (16)	0.0025 (17)	0.0058 (15)
C17	0.049 (2)	0.065 (2)	0.048 (2)	−0.0036 (18)	−0.0049 (16)	−0.0054 (16)
C18	0.064 (2)	0.0528 (18)	0.076 (2)	−0.009 (2)	−0.0280 (19)	−0.011 (2)
C20	0.0431 (19)	0.0358 (15)	0.0482 (17)	−0.0014 (14)	0.0043 (15)	−0.0004 (14)
C22	0.0300 (18)	0.0410 (16)	0.0378 (17)	0.0039 (13)	0.0077 (14)	−0.0015 (13)
C27	0.0271 (17)	0.0387 (15)	0.0341 (16)	0.0020 (12)	0.0056 (13)	−0.0019 (12)
C21	0.0327 (18)	0.0419 (15)	0.0363 (17)	0.0032 (13)	0.0064 (15)	−0.0005 (12)
C28	0.0286 (17)	0.0362 (15)	0.0347 (16)	0.0042 (12)	0.0048 (14)	0.0002 (12)
C19	0.048 (2)	0.046 (2)	0.0414 (18)	0.0017 (14)	0.0059 (16)	−0.0128 (12)
N1	0.0402 (16)	0.0426 (13)	0.0399 (15)	−0.0010 (12)	0.0013 (13)	0.0031 (10)
N2	0.0426 (17)	0.0377 (13)	0.0371 (14)	−0.0006 (11)	−0.0098 (13)	0.0006 (11)
O1	0.0606 (16)	0.0558 (13)	0.0660 (16)	−0.0128 (12)	0.0143 (12)	0.0043 (11)
O2	0.0664 (18)	0.0542 (14)	0.0728 (16)	−0.0012 (12)	−0.0136 (13)	0.0196 (11)
S1	0.0572 (6)	0.0374 (4)	0.0534 (5)	−0.0046 (4)	0.0106 (4)	0.0005 (4)
S2	0.0444 (5)	0.0419 (4)	0.0493 (4)	0.0005 (4)	0.0001 (4)	0.0096 (4)

C9—C10	1.361 (4)	C23—C24	1.364 (4)
C9—C8	1.389 (4)	C23—C22	1.380 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.389 (4)	C24—C25	1.387 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.375 (4)	C25—C26	1.378 (4)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.385 (4)	C26—C27	1.389 (3)
C12—H12	0.9300	C26—H26	0.9300
C15—N1	1.454 (3)	C29—N2	1.449 (3)
C15—C14	1.493 (4)	C29—C28	1.495 (3)
C15—H15B	0.9700	C29—H29B	0.9700
C15—H15A	0.9700	C29—H29A	0.9700
C2—O1	1.214 (3)	C16—O2	1.222 (3)
C2—N1	1.358 (4)	C16—N2	1.333 (3)
C2—C3	1.505 (4)	C16—C17	1.497 (4)
C3—C4	1.514 (4)	C17—C18	1.490 (4)
C3—H3B	0.9700	C17—H17B	0.9700
C3—H3A	0.9700	C17—H17A	0.9700
C4—C5	1.522 (4)	C18—C19	1.520 (4)
C4—H4B	0.9700	C18—H18B	0.9700
C4—H4A	0.9700	C18—H18A	0.9700
C6—C7	1.496 (4)	C20—C21	1.497 (4)
C6—C5	1.516 (3)	C20—C19	1.512 (3)
C6—H6B	0.9700	C20—H20B	0.9700
C6—H6A	0.9700	C20—H20A	0.9700
C8—C13	1.405 (3)	C22—C27	1.399 (3)
C8—S1	1.736 (3)	C22—S2	1.735 (3)
C13—C14	1.428 (4)	C27—C28	1.443 (4)
C7—C14	1.343 (3)	C21—C28	1.333 (3)
C7—S1	1.742 (3)	C21—S2	1.739 (3)
C5—N1	1.449 (3)	C19—N2	1.461 (3)
C5—H5	0.9800	C19—H19	0.9800
C10—C9—C8	119.1 (3)	C23—C24—H24	119.8
C10—C9—H9	120.5	C25—C24—H24	119.8
C8—C9—H9	120.5	C26—C25—C24	120.9 (3)
C9—C10—C11	120.3 (3)	C26—C25—H25	119.5
C9—C10—H10	119.9	C24—C25—H25	119.5
C11—C10—H10	119.9	C25—C26—C27	119.5 (3)
C12—C11—C10	120.8 (3)	C25—C26—H26	120.2
C12—C11—H11	119.6	C27—C26—H26	120.2
C10—C11—H11	119.6	N2—C29—C28	109.9 (2)
C11—C12—C13	120.5 (3)	N2—C29—H29B	109.7
C11—C12—H12	119.8	C28—C29—H29B	109.7
C13—C12—H12	119.8	N2—C29—H29A	109.7
N1—C15—C14	110.4 (2)	C28—C29—H29A	109.7
N1—C15—H15B	109.6	H29B—C29—H29A	108.2
C14—C15—H15B	109.6	O2—C16—N2	125.2 (3)
N1—C15—H15A	109.6	O2—C16—C17	126.6 (3)
C14—C15—H15A	109.6	N2—C16—C17	108.2 (2)
H15B—C15—H15A	108.1	C18—C17—C16	105.4 (2)
O1—C2—N1	125.1 (3)	C18—C17—H17B	110.7
O1—C2—C3	127.7 (3)	C16—C17—H17B	110.7
N1—C2—C3	107.2 (3)	C18—C17—H17A	110.7
C2—C3—C4	105.8 (3)	C16—C17—H17A	110.7
C2—C3—H3B	110.6	H17B—C17—H17A	108.8
C4—C3—H3B	110.6	C17—C18—C19	105.8 (3)
C2—C3—H3A	110.6	C17—C18—H18B	110.6
C4—C3—H3A	110.6	C19—C18—H18B	110.6
H3B—C3—H3A	108.7	C17—C18—H18A	110.6
C3—C4—C5	105.4 (2)	C19—C18—H18A	110.6
C3—C4—H4B	110.7	H18B—C18—H18A	108.7
C5—C4—H4B	110.7	C21—C20—C19	109.3 (2)
C3—C4—H4A	110.7	C21—C20—H20B	109.8
C5—C4—H4A	110.7	C19—C20—H20B	109.8
H4B—C4—H4A	108.8	C21—C20—H20A	109.8
C7—C6—C5	109.5 (2)	C19—C20—H20A	109.8
C7—C6—H6B	109.8	H20B—C20—H20A	108.3
C5—C6—H6B	109.8	C23—C22—C27	121.6 (2)
C7—C6—H6A	109.8	C23—C22—S2	127.6 (2)
C5—C6—H6A	109.8	C27—C22—S2	110.82 (19)
H6B—C6—H6A	108.2	C26—C27—C22	118.5 (2)
C9—C8—C13	121.7 (3)	C26—C27—C28	129.5 (2)
C9—C8—S1	127.3 (2)	C22—C27—C28	111.9 (2)
C13—C8—S1	111.0 (2)	C28—C21—C20	125.3 (3)
C12—C13—C8	117.7 (2)	C28—C21—S2	113.0 (2)
C12—C13—C14	130.5 (2)	C20—C21—S2	121.7 (2)
C8—C13—C14	111.8 (2)	C21—C28—C27	112.9 (2)
C14—C7—C6	125.6 (2)	C21—C28—C29	123.0 (3)
C14—C7—S1	112.4 (2)	C27—C28—C29	124.1 (2)
C6—C7—S1	121.96 (19)	N2—C19—C20	110.9 (2)
C7—C14—C13	113.5 (2)	N2—C19—C18	102.5 (3)
C7—C14—C15	121.8 (2)	C20—C19—C18	114.4 (3)
C13—C14—C15	124.7 (2)	N2—C19—H19	109.6
N1—C5—C6	110.4 (2)	C20—C19—H19	109.6
N1—C5—C4	103.4 (2)	C18—C19—H19	109.6
C6—C5—C4	114.2 (2)	C2—N1—C5	114.7 (2)
N1—C5—H5	109.5	C2—N1—C15	122.8 (2)
C6—C5—H5	109.5	C5—N1—C15	121.0 (2)
C4—C5—H5	109.5	C16—N2—C29	123.2 (2)
C24—C23—C22	119.0 (3)	C16—N2—C19	114.1 (2)
C24—C23—H23	120.5	C29—N2—C19	121.6 (2)
C22—C23—H23	120.5	C8—S1—C7	91.27 (13)
C23—C24—C25	120.4 (3)	C22—S2—C21	91.34 (13)
C8—C9—C10—C11	1.2 (5)	C19—C20—C21—C28	−21.4 (4)
C9—C10—C11—C12	−1.4 (5)	C19—C20—C21—S2	160.9 (2)
C10—C11—C12—C13	0.6 (5)	C20—C21—C28—C27	−178.7 (3)
O1—C2—C3—C4	175.0 (3)	S2—C21—C28—C27	−0.9 (3)
N1—C2—C3—C4	−7.1 (3)	C20—C21—C28—C29	1.1 (4)
C2—C3—C4—C5	15.9 (3)	S2—C21—C28—C29	179.0 (2)
C10—C9—C8—C13	−0.1 (5)	C26—C27—C28—C21	179.2 (3)
C10—C9—C8—S1	178.7 (2)	C22—C27—C28—C21	2.2 (3)
C11—C12—C13—C8	0.4 (4)	C26—C27—C28—C29	−0.7 (5)
C11—C12—C13—C14	−178.5 (3)	C22—C27—C28—C29	−177.7 (2)
C9—C8—C13—C12	−0.7 (4)	N2—C29—C28—C21	−4.3 (4)
S1—C8—C13—C12	−179.7 (2)	N2—C29—C28—C27	175.6 (3)
C9—C8—C13—C14	178.4 (3)	C21—C20—C19—N2	43.4 (3)
S1—C8—C13—C14	−0.6 (3)	C21—C20—C19—C18	158.6 (3)
C5—C6—C7—C14	−20.3 (4)	C17—C18—C19—N2	−19.3 (3)
C5—C6—C7—S1	161.2 (2)	C17—C18—C19—C20	−139.3 (3)
C6—C7—C14—C13	−179.1 (3)	O1—C2—N1—C5	172.6 (3)
S1—C7—C14—C13	−0.5 (3)	C3—C2—N1—C5	−5.3 (3)
C6—C7—C14—C15	1.1 (5)	O1—C2—N1—C15	6.3 (5)
S1—C7—C14—C15	179.8 (2)	C3—C2—N1—C15	−171.7 (2)
C12—C13—C14—C7	179.6 (3)	C6—C5—N1—C2	137.8 (3)
C8—C13—C14—C7	0.7 (4)	C4—C5—N1—C2	15.3 (3)
C12—C13—C14—C15	−0.7 (5)	C6—C5—N1—C15	−55.6 (3)
C8—C13—C14—C15	−179.6 (3)	C4—C5—N1—C15	−178.1 (2)
N1—C15—C14—C7	−6.2 (4)	C14—C15—N1—C2	−159.5 (3)
N1—C15—C14—C13	174.1 (3)	C14—C15—N1—C5	35.0 (4)
C7—C6—C5—N1	43.3 (3)	O2—C16—N2—C29	8.5 (5)
C7—C6—C5—C4	159.2 (3)	C17—C16—N2—C29	−172.7 (3)
C3—C4—C5—N1	−18.4 (3)	O2—C16—N2—C19	177.2 (3)
C3—C4—C5—C6	−138.4 (2)	C17—C16—N2—C19	−4.1 (4)
C22—C23—C24—C25	1.1 (4)	C28—C29—N2—C16	−160.2 (3)
C23—C24—C25—C26	−0.6 (5)	C28—C29—N2—C19	31.9 (3)
C24—C25—C26—C27	−0.7 (5)	C20—C19—N2—C16	137.3 (3)
O2—C16—C17—C18	169.8 (3)	C18—C19—N2—C16	14.9 (3)
N2—C16—C17—C18	−8.9 (4)	C20—C19—N2—C29	−53.8 (3)
C16—C17—C18—C19	17.6 (4)	C18—C19—N2—C29	−176.3 (3)
C24—C23—C22—C27	−0.2 (4)	C9—C8—S1—C7	−178.7 (3)
C24—C23—C22—S2	178.3 (2)	C13—C8—S1—C7	0.3 (2)
C25—C26—C27—C22	1.5 (4)	C14—C7—S1—C8	0.1 (2)
C25—C26—C27—C28	−175.3 (3)	C6—C7—S1—C8	178.8 (3)
C23—C22—C27—C26	−1.1 (4)	C23—C22—S2—C21	−177.0 (3)
S2—C22—C27—C26	−179.8 (2)	C27—C22—S2—C21	1.7 (2)
C23—C22—C27—C28	176.3 (3)	C28—C21—S2—C22	−0.5 (2)
S2—C22—C27—C28	−2.5 (3)	C20—C21—S2—C22	177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2i	0.97	2.48	3.307 (4)	144
C3—H3B···Cg14	0.97	2.59	3.502 (3)	157
C17—H17A···Cg4	0.97	2.92	3.800 (4)	151
C29—H29B···Cg4ii	0.97	2.90	3.706 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg14 are the centroids of the C8–C13 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O2i	0.97	2.48	3.307 (4)	144
C3—H3B⋯Cg14	0.97	2.59	3.502 (3)	157
C17—H17A⋯Cg4	0.97	2.92	3.800 (4)	151
C29—H29B⋯Cg4ii	0.97	2.90	3.706 (3)	142

Symmetry codes: (i) ; (ii) .