Synthesis and properties of a novel deca­cyclic S,N-hetero­acene

Li, G.; Wang, W.; Xiao, S.; Zhan, C.

doi:10.1107/S2053229622003291

Synthesis and properties of a novel decacyclic S,N-heteroacene

S,N-Heteroacene materials with fused multicyclic heteroaromatics have become increasingly attractive for organic optoelectronic device applications. In this work, the Cadogan ring-closure reaction between the benzene moiety of thieno[3,2-b]indole and 5,6-dinitrobenzo[c][1,2,5]thiadiazole was employed to prepare the novel decacyclic S,N-heteroacene 15,16-dibutyl-14,17-didodecyldithieno[2′′,3′′:2′,3′]indolo[6′,7′:4,5]pyrrolo[3,2-e:2′,3′-g][2,1,3]benzothiadiazole (TIP), C₅₈H₇₆N₆S₃. The conjugated backbone of TIP is extended in comparison with its octacyclic analogue as the central unit within Y6-type molecular acceptors, a family of overwhelming electron acceptors in polymer solar-cell research. The single-crystal X-ray diffraction (SC-XRD) characterization indicated the existence of π–π and C(sp²)—H

π interactions among TIP molecules. The electrochemical and optical properties of TIP were also characterized. As a novel S,N-heteroacene building block, TIP is anticipated to be of potential use in the construction of promising electronic materials.

Keywords: S,N-heteroacene; Cadogan reaction; crystal structure; single-crystal X-ray diffraction; π–π interaction; C—H

π interaction; optoelectronic device.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622003291/yp3223sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622003291/yp3223Isup2.hkl Contains datablock I
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622003291/yp3223sup3.pdf Additional figures and tables

CCDC reference: 2130077

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and OLEX2 (Dolomanov et al., 2009).

15,16-Dibutyl-14,17-didodecyldithieno[2'',3'':2',3']indolo[6',7':4,5]pyrrolo[3,2-e:2',3'-g][2,1,3]benzothiadiazole top

Crystal data top

C₅₈H₇₆N₆S₃	F(000) = 2056
M_r = 953.42	D_x = 1.219 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 26.4610 (3) Å	Cell parameters from 19978 reflections
b = 21.2115 (3) Å	θ = 2.6–76.0°
c = 9.2552 (1) Å	µ = 1.63 mm⁻¹
β = 90.044 (1)°	T = 170 K
V = 5194.73 (11) Å³	Plate, fluorescent intense orange
Z = 4	0.35 × 0.10 × 0.05 mm

Data collection top

XtaLAB Synergy R, HyPix diffractometer	9390 reflections with I > 2σ(I)
ω scans	R_int = 0.033
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	θ_max = 77.0°, θ_min = 2.7°
T_min = 0.904, T_max = 1.000	h = −32→33
38886 measured reflections	k = −21→26
10579 independent reflections	l = −11→11

Refinement top

Refinement on F²	11 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0567P)² + 2.7445P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
10579 reflections	Δρ_max = 1.04 e Å⁻³
640 parameters	Δρ_min = −1.15 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.02124 (2)	−0.55840 (2)	0.28343 (5)	0.03572 (11)
S2	−0.25271 (2)	−0.28861 (2)	−0.12819 (4)	0.03141 (11)
S3	−0.54959 (2)	−0.29284 (2)	0.54623 (5)	0.02991 (10)
N1	−0.10400 (5)	−0.52893 (6)	0.47675 (15)	0.0256 (3)
N2	−0.20341 (5)	−0.43577 (6)	0.40779 (14)	0.0225 (3)
N3	−0.21034 (5)	−0.33187 (7)	−0.04713 (15)	0.0283 (3)
N4	−0.29717 (5)	−0.28823 (6)	−0.00690 (15)	0.0279 (3)
N5	−0.31759 (5)	−0.38821 (6)	0.45091 (14)	0.0211 (3)
N6	−0.42069 (5)	−0.36469 (6)	0.63270 (14)	0.0242 (3)
C1	0.01986 (7)	−0.60268 (9)	0.4410 (2)	0.0378 (4)
H1	0.046987	−0.629051	0.470492	0.045*
C2	−0.02332 (7)	−0.59635 (9)	0.5182 (2)	0.0345 (4)
H2	−0.030346	−0.617272	0.606740	0.041*
C3	−0.05653 (6)	−0.55377 (8)	0.44719 (19)	0.0282 (3)
C4	−0.03843 (6)	−0.52970 (8)	0.32020 (19)	0.0293 (3)
C5	−0.07532 (6)	−0.48806 (8)	0.26159 (18)	0.0272 (3)
C6	−0.07685 (6)	−0.45339 (9)	0.13221 (19)	0.0313 (4)
H6	−0.048782	−0.454006	0.068305	0.038*
C7	−0.11885 (6)	−0.41878 (8)	0.09855 (18)	0.0293 (3)
H7	−0.120908	−0.396605	0.009562	0.035*
C8	−0.15912 (6)	−0.41661 (8)	0.19857 (17)	0.0246 (3)
C9	−0.20677 (6)	−0.38524 (7)	0.19039 (16)	0.0233 (3)
C10	−0.23298 (5)	−0.39811 (7)	0.31722 (16)	0.0217 (3)
C11	−0.15802 (6)	−0.44867 (7)	0.33261 (16)	0.0229 (3)
C12	−0.11612 (6)	−0.48793 (7)	0.36323 (17)	0.0242 (3)
C13	−0.22989 (6)	−0.34774 (7)	0.08072 (16)	0.0232 (3)
C14	−0.27989 (6)	−0.32277 (7)	0.10372 (16)	0.0231 (3)
C15	−0.30658 (6)	−0.33850 (7)	0.23253 (16)	0.0222 (3)
C16	−0.28353 (5)	−0.37607 (7)	0.33691 (16)	0.0214 (3)
C17	−0.36207 (5)	−0.35437 (7)	0.41510 (16)	0.0212 (3)
C18	−0.35743 (6)	−0.32574 (7)	0.27939 (16)	0.0219 (3)
C19	−0.39858 (6)	−0.29616 (7)	0.21010 (17)	0.0247 (3)
H19	−0.394642	−0.277479	0.117506	0.030*
C20	−0.44454 (6)	−0.29493 (7)	0.27938 (17)	0.0253 (3)
H20	−0.473421	−0.278275	0.231791	0.030*
C21	−0.44858 (6)	−0.31845 (7)	0.42116 (17)	0.0232 (3)
C22	−0.40719 (6)	−0.34733 (7)	0.49296 (16)	0.0220 (3)
C23	−0.48867 (6)	−0.31975 (7)	0.52471 (17)	0.0248 (3)
C24	−0.47081 (6)	−0.34649 (7)	0.65075 (17)	0.0248 (3)
C25	−0.50601 (6)	−0.34545 (8)	0.76663 (19)	0.0296 (3)
H25	−0.499727	−0.361704	0.860587	0.036*
C26	−0.55001 (6)	−0.31786 (8)	0.72389 (19)	0.0314 (4)
H26	−0.578306	−0.312831	0.785963	0.038*
C27	−0.13638 (6)	−0.55607 (8)	0.58798 (18)	0.0287 (3)
C28	−0.17707 (6)	−0.60011 (8)	0.52828 (19)	0.0317 (4)
H28A	−0.202574	−0.608056	0.604340	0.038*
H28B	−0.194333	−0.579189	0.446352	0.038*
C29	−0.15548 (7)	−0.66287 (9)	0.4773 (2)	0.0364 (4)
H29A	−0.143973	−0.686908	0.562924	0.044*
H29B	−0.125428	−0.654342	0.416715	0.044*
C30	−0.19200 (8)	−0.70399 (9)	0.3913 (2)	0.0389 (4)
H30A	−0.172499	−0.738814	0.347027	0.047*
H30B	−0.206083	−0.678299	0.311537	0.047*
C31	−0.23598 (7)	−0.73258 (9)	0.4754 (2)	0.0347 (4)
H31A	−0.222534	−0.759730	0.553526	0.042*
H31B	−0.255842	−0.698343	0.520768	0.042*
C32	−0.27046 (7)	−0.77154 (9)	0.3783 (2)	0.0373 (4)
H32A	−0.282494	−0.744174	0.298757	0.045*
H32B	−0.250102	−0.805681	0.334428	0.045*
C33	−0.31638 (7)	−0.80119 (9)	0.4507 (2)	0.0360 (4)
H33A	−0.336172	−0.767824	0.499570	0.043*
H33B	−0.304846	−0.831398	0.525273	0.043*
C34	−0.35027 (7)	−0.83543 (9)	0.3431 (2)	0.0388 (4)
H34A	−0.362147	−0.804555	0.270380	0.047*
H34B	−0.329679	−0.867292	0.291741	0.047*
C35	−0.39616 (7)	−0.86823 (8)	0.4073 (2)	0.0350 (4)
H35A	−0.416010	−0.837159	0.463422	0.042*
H35B	−0.384551	−0.901342	0.475030	0.042*
C36	−0.43024 (7)	−0.89810 (9)	0.2939 (2)	0.0381 (4)
H36A	−0.410227	−0.929200	0.238420	0.046*
H36B	−0.441327	−0.864895	0.225761	0.046*
C37	−0.47685 (8)	−0.93094 (10)	0.3540 (2)	0.0429 (4)
H37A	−0.466166	−0.960864	0.430223	0.051*
H37B	−0.498992	−0.899015	0.399586	0.051*
C38	−0.50708 (8)	−0.96655 (11)	0.2408 (3)	0.0534 (6)
H38A	−0.517721	−0.937359	0.164562	0.080*
H38B	−0.536968	−0.985392	0.285977	0.080*
H38C	−0.486059	−0.999882	0.198854	0.080*
C39	−0.20681 (6)	−0.42725 (8)	0.56591 (17)	0.0251 (3)
C40	−0.16319 (6)	−0.38938 (8)	0.62948 (17)	0.0279 (3)
H40A	−0.130932	−0.410492	0.605182	0.033*
H40B	−0.166366	−0.388761	0.736041	0.033*
C41	−0.16173 (7)	−0.32179 (9)	0.5738 (2)	0.0370 (4)
H41A	−0.196368	−0.304168	0.575934	0.044*
H41B	−0.150292	−0.322041	0.471968	0.044*
C42	−0.12690 (8)	−0.27914 (10)	0.6615 (2)	0.0457 (5)
H42A	−0.127048	−0.236677	0.619750	0.069*
H42B	−0.092459	−0.296113	0.659372	0.069*
H42C	−0.138798	−0.277231	0.761610	0.069*
C47	−0.38579 (6)	−0.37268 (7)	0.75513 (17)	0.0247 (3)
H47A	−0.387837	−0.335268	0.818808	0.030*
H47B	−0.350735	−0.375773	0.718479	0.030*
C48	−0.39836 (6)	−0.43161 (8)	0.84199 (18)	0.0280 (3)
H48A	−0.430969	−0.424851	0.892030	0.034*
H48B	−0.402911	−0.467266	0.774177	0.034*
C49	−0.35876 (6)	−0.44995 (8)	0.95374 (18)	0.0283 (3)
H49A	−0.372903	−0.483379	1.016451	0.034*
H49B	−0.351574	−0.412892	1.015455	0.034*
C50	−0.30914 (6)	−0.47350 (8)	0.88900 (18)	0.0306 (3)
H50A	−0.316855	−0.502005	0.807207	0.037*
H50B	−0.290182	−0.437015	0.850137	0.037*
C51	−0.27573 (6)	−0.50833 (8)	0.99651 (18)	0.0294 (3)
H51A	−0.267687	−0.479668	1.077760	0.035*
H51B	−0.294817	−0.544536	1.036199	0.035*
C52	−0.22661 (7)	−0.53237 (9)	0.93151 (19)	0.0345 (4)
H52A	−0.205756	−0.495849	0.901867	0.041*
H52B	−0.234461	−0.557149	0.843671	0.041*
C53	−0.19602 (7)	−0.57330 (9)	1.03481 (19)	0.0328 (4)
H53A	−0.187359	−0.548105	1.121401	0.039*
H53B	−0.217255	−0.609111	1.066699	0.039*
C54	−0.14750 (7)	−0.59905 (9)	0.9690 (2)	0.0354 (4)
H54A	−0.126108	−0.563245	0.937963	0.043*
H54B	−0.156126	−0.623919	0.881849	0.043*
C55	−0.11724 (7)	−0.64045 (9)	1.0719 (2)	0.0354 (4)
H55A	−0.110507	−0.616345	1.161499	0.042*
H55B	−0.138028	−0.677496	1.098381	0.042*
C56	−0.06724 (7)	−0.66349 (10)	1.0110 (2)	0.0431 (4)
H56A	−0.073779	−0.686218	0.919480	0.052*
H56B	−0.045832	−0.626524	0.988346	0.052*
C57	−0.03846 (8)	−0.70668 (10)	1.1124 (3)	0.0497 (5)
H57A	−0.033567	−0.684920	1.205962	0.060*
H57B	−0.058953	−0.744919	1.130471	0.060*
C58	0.01265 (9)	−0.72627 (13)	1.0537 (4)	0.0684 (8)
H58A	0.008153	−0.747476	0.960510	0.103*
H58B	0.028963	−0.755157	1.121952	0.103*
H58C	0.033872	−0.688834	1.040744	0.103*
C44B	−0.35087 (14)	−0.49057 (16)	0.3552 (4)	0.0343 (8)	0.65
H44A	−0.380314	−0.465947	0.320931	0.041*	0.65
H44B	−0.325913	−0.492172	0.275674	0.041*	0.65
C45B	−0.36792 (14)	−0.55706 (16)	0.3899 (4)	0.0368 (6)	0.52
H45A	−0.386319	−0.574122	0.305335	0.044*	0.52
H45B	−0.391995	−0.555312	0.471657	0.044*	0.52
C46A	−0.3290 (3)	−0.6186 (3)	0.3230 (11)	0.0603 (10)	0.3
H46A	−0.351225	−0.610008	0.240558	0.090*	0.3
H46B	−0.336815	−0.660330	0.362656	0.090*	0.3
H46C	−0.293710	−0.617577	0.291266	0.090*	0.3
C46B	−0.32556 (14)	−0.60220 (16)	0.4286 (5)	0.0603 (10)	0.7
H46D	−0.302634	−0.606558	0.346133	0.090*	0.7
H46E	−0.339837	−0.643485	0.452928	0.090*	0.7
H46F	−0.306845	−0.585704	0.511862	0.090*	0.7
C44A	−0.3275 (3)	−0.5011 (3)	0.3809 (6)	0.0341 (13)	0.35
H44C	−0.294844	−0.500569	0.328783	0.041*	0.35
H44D	−0.354362	−0.490117	0.310809	0.041*	0.35
C45A	−0.33726 (17)	−0.5689 (2)	0.4387 (5)	0.0368 (6)	0.48
H45C	−0.314303	−0.577251	0.520988	0.044*	0.48
H45D	−0.372424	−0.571734	0.474560	0.044*	0.48
C43	−0.32632 (6)	−0.45545 (7)	0.48928 (18)	0.0267 (3)
H43A	−0.349164	−0.458193	0.573704	0.032*
H43B	−0.293858	−0.475746	0.515153	0.032*
H39A	−0.2103 (7)	−0.4685 (9)	0.613 (2)	0.027 (5)*
H39B	−0.2381 (7)	−0.4035 (9)	0.583 (2)	0.023 (4)*
H27A	−0.1141 (7)	−0.5806 (9)	0.651 (2)	0.025 (5)*
H27B	−0.1514 (7)	−0.5228 (10)	0.648 (2)	0.031 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02174 (19)	0.0377 (2)	0.0477 (3)	0.00609 (16)	0.00393 (17)	−0.00549 (19)
S2	0.0346 (2)	0.0344 (2)	0.0252 (2)	0.00567 (17)	0.00398 (15)	0.00787 (16)
S3	0.01969 (18)	0.0347 (2)	0.0354 (2)	0.00508 (15)	0.00016 (15)	−0.00288 (16)
N1	0.0194 (6)	0.0286 (7)	0.0289 (7)	0.0038 (5)	−0.0015 (5)	0.0009 (5)
N2	0.0186 (6)	0.0265 (7)	0.0225 (6)	0.0017 (5)	0.0007 (5)	0.0009 (5)
N3	0.0305 (7)	0.0295 (7)	0.0249 (7)	0.0019 (6)	0.0034 (5)	0.0040 (5)
N4	0.0297 (7)	0.0281 (7)	0.0261 (7)	0.0022 (5)	−0.0001 (5)	0.0037 (5)
N5	0.0173 (6)	0.0224 (6)	0.0237 (6)	0.0008 (5)	0.0009 (5)	0.0015 (5)
N6	0.0196 (6)	0.0285 (7)	0.0245 (6)	0.0024 (5)	0.0011 (5)	0.0007 (5)
C1	0.0259 (8)	0.0343 (9)	0.0533 (11)	0.0074 (7)	−0.0040 (8)	−0.0027 (8)
C2	0.0272 (8)	0.0324 (9)	0.0438 (10)	0.0048 (7)	−0.0047 (7)	0.0000 (7)
C3	0.0198 (7)	0.0290 (8)	0.0358 (9)	0.0029 (6)	−0.0029 (6)	−0.0040 (7)
C4	0.0213 (7)	0.0314 (9)	0.0352 (9)	0.0016 (6)	0.0012 (6)	−0.0046 (7)
C5	0.0213 (7)	0.0302 (8)	0.0303 (8)	0.0023 (6)	0.0019 (6)	−0.0038 (6)
C6	0.0240 (8)	0.0375 (9)	0.0324 (8)	0.0014 (7)	0.0079 (6)	−0.0010 (7)
C7	0.0267 (8)	0.0345 (9)	0.0267 (8)	0.0009 (7)	0.0046 (6)	0.0020 (7)
C8	0.0221 (7)	0.0272 (8)	0.0247 (7)	0.0002 (6)	0.0008 (6)	−0.0005 (6)
C9	0.0216 (7)	0.0246 (7)	0.0239 (7)	−0.0012 (6)	0.0006 (6)	−0.0006 (6)
C10	0.0198 (7)	0.0219 (7)	0.0233 (7)	−0.0005 (6)	−0.0013 (5)	−0.0002 (6)
C11	0.0186 (7)	0.0258 (8)	0.0244 (7)	−0.0002 (6)	0.0017 (6)	−0.0022 (6)
C12	0.0205 (7)	0.0267 (8)	0.0253 (7)	0.0008 (6)	−0.0009 (6)	−0.0018 (6)
C13	0.0238 (7)	0.0226 (7)	0.0231 (7)	−0.0017 (6)	0.0013 (6)	−0.0005 (6)
C14	0.0236 (7)	0.0207 (7)	0.0249 (7)	−0.0009 (6)	−0.0018 (6)	0.0001 (6)
C15	0.0212 (7)	0.0214 (7)	0.0240 (7)	−0.0003 (6)	−0.0008 (5)	−0.0007 (6)
C16	0.0202 (7)	0.0220 (7)	0.0220 (7)	−0.0016 (6)	−0.0001 (5)	−0.0010 (6)
C17	0.0183 (7)	0.0204 (7)	0.0247 (7)	0.0014 (5)	−0.0016 (5)	−0.0022 (6)
C18	0.0215 (7)	0.0190 (7)	0.0252 (7)	−0.0004 (6)	−0.0009 (6)	−0.0016 (6)
C19	0.0257 (8)	0.0229 (7)	0.0254 (7)	0.0020 (6)	−0.0021 (6)	0.0017 (6)
C20	0.0230 (7)	0.0234 (8)	0.0295 (8)	0.0042 (6)	−0.0043 (6)	0.0002 (6)
C21	0.0199 (7)	0.0214 (7)	0.0284 (8)	0.0016 (6)	−0.0006 (6)	−0.0033 (6)
C22	0.0215 (7)	0.0204 (7)	0.0242 (7)	0.0000 (6)	0.0002 (6)	−0.0017 (6)
C23	0.0216 (7)	0.0235 (7)	0.0293 (8)	0.0015 (6)	−0.0008 (6)	−0.0036 (6)
C24	0.0205 (7)	0.0240 (8)	0.0300 (8)	0.0004 (6)	0.0016 (6)	−0.0026 (6)
C25	0.0252 (8)	0.0324 (9)	0.0312 (8)	−0.0010 (6)	0.0044 (6)	−0.0009 (7)
C26	0.0232 (8)	0.0342 (9)	0.0368 (9)	−0.0002 (7)	0.0060 (6)	−0.0039 (7)
C27	0.0269 (8)	0.0311 (9)	0.0282 (8)	0.0050 (7)	0.0016 (6)	0.0021 (7)
C28	0.0268 (8)	0.0341 (9)	0.0342 (9)	0.0012 (7)	0.0021 (7)	0.0041 (7)
C29	0.0327 (9)	0.0367 (10)	0.0400 (10)	−0.0001 (7)	0.0039 (7)	−0.0009 (8)
C30	0.0432 (10)	0.0386 (10)	0.0349 (9)	−0.0046 (8)	0.0061 (8)	−0.0025 (8)
C31	0.0385 (9)	0.0331 (9)	0.0325 (9)	0.0003 (7)	0.0010 (7)	0.0016 (7)
C32	0.0424 (10)	0.0352 (9)	0.0342 (9)	−0.0033 (8)	0.0030 (8)	−0.0009 (7)
C33	0.0403 (10)	0.0320 (9)	0.0356 (9)	−0.0003 (7)	0.0009 (7)	0.0024 (7)
C34	0.0418 (10)	0.0350 (10)	0.0396 (10)	−0.0023 (8)	0.0027 (8)	0.0001 (8)
C35	0.0388 (9)	0.0295 (9)	0.0366 (9)	0.0032 (7)	0.0001 (7)	0.0028 (7)
C36	0.0424 (10)	0.0326 (9)	0.0393 (10)	0.0011 (8)	−0.0011 (8)	0.0045 (8)
C37	0.0375 (10)	0.0390 (10)	0.0521 (12)	0.0022 (8)	−0.0020 (9)	0.0044 (9)
C38	0.0429 (11)	0.0426 (12)	0.0748 (16)	0.0003 (9)	−0.0166 (11)	0.0107 (11)
C39	0.0210 (7)	0.0321 (8)	0.0224 (7)	0.0035 (6)	0.0016 (6)	0.0032 (6)
C40	0.0243 (8)	0.0345 (9)	0.0249 (8)	0.0038 (6)	−0.0001 (6)	−0.0026 (6)
C41	0.0380 (10)	0.0350 (9)	0.0381 (10)	0.0008 (8)	0.0007 (8)	−0.0015 (8)
C42	0.0371 (10)	0.0429 (11)	0.0573 (13)	−0.0048 (8)	0.0077 (9)	−0.0122 (9)
C47	0.0228 (7)	0.0253 (8)	0.0260 (7)	0.0005 (6)	−0.0017 (6)	−0.0006 (6)
C48	0.0260 (8)	0.0280 (8)	0.0299 (8)	−0.0014 (6)	−0.0006 (6)	0.0025 (6)
C49	0.0310 (8)	0.0277 (8)	0.0262 (8)	−0.0001 (6)	−0.0008 (6)	0.0028 (6)
C50	0.0308 (8)	0.0338 (9)	0.0271 (8)	0.0028 (7)	−0.0028 (6)	0.0030 (7)
C51	0.0299 (8)	0.0304 (8)	0.0279 (8)	0.0006 (7)	−0.0036 (6)	0.0024 (6)
C52	0.0333 (9)	0.0403 (10)	0.0300 (8)	0.0057 (8)	−0.0016 (7)	0.0036 (7)
C53	0.0320 (9)	0.0358 (9)	0.0306 (8)	0.0037 (7)	−0.0023 (7)	0.0029 (7)
C54	0.0327 (9)	0.0406 (10)	0.0331 (9)	0.0038 (7)	−0.0007 (7)	0.0032 (7)
C55	0.0330 (9)	0.0377 (10)	0.0355 (9)	0.0034 (7)	−0.0018 (7)	0.0024 (7)
C56	0.0322 (9)	0.0478 (11)	0.0494 (11)	0.0051 (8)	−0.0012 (8)	−0.0005 (9)
C57	0.0365 (10)	0.0429 (11)	0.0695 (15)	0.0048 (9)	−0.0138 (10)	−0.0048 (10)
C58	0.0396 (12)	0.0606 (15)	0.105 (2)	0.0146 (11)	−0.0148 (13)	−0.0186 (15)
C44B	0.0369 (18)	0.0293 (16)	0.0368 (16)	0.0001 (14)	−0.0161 (15)	−0.0009 (12)
C45B	0.0359 (15)	0.0279 (13)	0.0467 (16)	−0.0048 (13)	−0.0013 (11)	−0.0020 (12)
C46A	0.0542 (18)	0.0219 (15)	0.105 (3)	0.0043 (13)	−0.010 (2)	−0.0024 (17)
C46B	0.0542 (18)	0.0219 (15)	0.105 (3)	0.0043 (13)	−0.010 (2)	−0.0024 (17)
C44A	0.046 (4)	0.031 (3)	0.026 (3)	−0.008 (3)	0.010 (3)	−0.001 (2)
C45A	0.0359 (15)	0.0279 (13)	0.0467 (16)	−0.0048 (13)	−0.0013 (11)	−0.0020 (12)
C43	0.0245 (8)	0.0223 (8)	0.0332 (8)	0.0021 (6)	0.0045 (6)	0.0046 (6)

Geometric parameters (Å, º) top

S1—C4	1.7263 (16)	C35—H35A	0.9900
S1—C1	1.735 (2)	C35—H35B	0.9900
S2—N4	1.6268 (14)	C36—C37	1.522 (3)
S2—N3	1.6311 (14)	C36—H36A	0.9900
S3—C23	1.7220 (15)	C36—H36B	0.9900
S3—C26	1.7278 (19)	C37—C38	1.519 (3)
N1—C3	1.389 (2)	C37—H37A	0.9900
N1—C12	1.401 (2)	C37—H37B	0.9900
N1—C27	1.458 (2)	C38—H38A	0.9800
N2—C10	1.3970 (19)	C38—H38B	0.9800
N2—C11	1.4154 (19)	C38—H38C	0.9800
N2—C39	1.4774 (19)	C39—C40	1.524 (2)
N3—C13	1.335 (2)	C39—H39A	0.98 (2)
N4—C14	1.339 (2)	C39—H39B	0.981 (19)
N5—C16	1.4118 (19)	C40—C41	1.524 (3)
N5—C17	1.4178 (19)	C40—H40A	0.9900
N5—C43	1.488 (2)	C40—H40B	0.9900
N6—C24	1.3914 (19)	C41—C42	1.525 (3)
N6—C22	1.392 (2)	C41—H41A	0.9900
N6—C47	1.471 (2)	C41—H41B	0.9900
C1—C2	1.355 (3)	C42—H42A	0.9800
C1—H1	0.9500	C42—H42B	0.9800
C2—C3	1.421 (2)	C42—H42C	0.9800
C2—H2	0.9500	C47—C48	1.523 (2)
C3—C4	1.368 (2)	C47—H47A	0.9900
C4—C5	1.424 (2)	C47—H47B	0.9900
C5—C6	1.406 (2)	C48—C49	1.522 (2)
C5—C12	1.432 (2)	C48—H48A	0.9900
C6—C7	1.368 (2)	C48—H48B	0.9900
C6—H6	0.9500	C49—C50	1.528 (2)
C7—C8	1.413 (2)	C49—H49A	0.9900
C7—H7	0.9500	C49—H49B	0.9900
C8—C11	1.415 (2)	C50—C51	1.522 (2)
C8—C9	1.428 (2)	C50—H50A	0.9900
C9—C10	1.391 (2)	C50—H50B	0.9900
C9—C13	1.427 (2)	C51—C52	1.521 (2)
C10—C16	1.429 (2)	C51—H51A	0.9900
C11—C12	1.415 (2)	C51—H51B	0.9900
C13—C14	1.441 (2)	C52—C53	1.524 (2)
C14—C15	1.426 (2)	C52—H52A	0.9900
C15—C16	1.393 (2)	C52—H52B	0.9900
C15—C18	1.440 (2)	C53—C54	1.523 (2)
C17—C18	1.401 (2)	C53—H53A	0.9900
C17—C22	1.403 (2)	C53—H53B	0.9900
C18—C19	1.410 (2)	C54—C55	1.523 (2)
C19—C20	1.375 (2)	C54—H54A	0.9900
C19—H19	0.9500	C54—H54B	0.9900
C20—C21	1.408 (2)	C55—C56	1.519 (3)
C20—H20	0.9500	C55—H55A	0.9900
C21—C22	1.419 (2)	C55—H55B	0.9900
C21—C23	1.430 (2)	C56—C57	1.516 (3)
C23—C24	1.380 (2)	C56—H56A	0.9900
C24—C25	1.421 (2)	C56—H56B	0.9900
C25—C26	1.362 (2)	C57—C58	1.516 (3)
C25—H25	0.9500	C57—H57A	0.9900
C26—H26	0.9500	C57—H57B	0.9900
C27—C28	1.528 (2)	C58—H58A	0.9800
C27—H27A	0.979 (19)	C58—H58B	0.9800
C27—H27B	0.98 (2)	C58—H58C	0.9800
C28—C29	1.524 (3)	C44B—C45B	1.515 (5)
C28—H28A	0.9900	C44B—C43	1.586 (4)
C28—H28B	0.9900	C44B—H44A	0.9900
C29—C30	1.526 (3)	C44B—H44B	0.9900
C29—H29A	0.9900	C45B—C46B	1.517 (5)
C29—H29B	0.9900	C45B—H45A	0.9900
C30—C31	1.527 (3)	C45B—H45B	0.9900
C30—H30A	0.9900	C46A—C45A	1.519 (9)
C30—H30B	0.9900	C46A—H46A	0.9800
C31—C32	1.524 (3)	C46A—H46B	0.9800
C31—H31A	0.9900	C46A—H46C	0.9800
C31—H31B	0.9900	C46B—H46D	0.9800
C32—C33	1.524 (3)	C46B—H46E	0.9800
C32—H32A	0.9900	C46B—H46F	0.9800
C32—H32B	0.9900	C44A—C43	1.394 (6)
C33—C34	1.524 (3)	C44A—C45A	1.555 (7)
C33—H33A	0.9900	C44A—H44C	0.9900
C33—H33B	0.9900	C44A—H44D	0.9900
C34—C35	1.521 (3)	C45A—H45C	0.9900
C34—H34A	0.9900	C45A—H45D	0.9900
C34—H34B	0.9900	C43—H43A	0.9900
C35—C36	1.521 (3)	C43—H43B	0.9900

C4—S1—C1	90.30 (9)	C37—C36—H36B	108.6
N4—S2—N3	100.52 (7)	H36A—C36—H36B	107.6
C23—S3—C26	90.86 (8)	C38—C37—C36	113.71 (18)
C3—N1—C12	107.11 (13)	C38—C37—H37A	108.8
C3—N1—C27	121.40 (14)	C36—C37—H37A	108.8
C12—N1—C27	129.80 (13)	C38—C37—H37B	108.8
C10—N2—C11	106.90 (12)	C36—C37—H37B	108.8
C10—N2—C39	119.34 (12)	H37A—C37—H37B	107.7
C11—N2—C39	124.25 (12)	C37—C38—H38A	109.5
C13—N3—S2	106.42 (11)	C37—C38—H38B	109.5
C14—N4—S2	106.15 (11)	H38A—C38—H38B	109.5
C16—N5—C17	105.27 (12)	C37—C38—H38C	109.5
C16—N5—C43	116.90 (12)	H38A—C38—H38C	109.5
C17—N5—C43	114.34 (12)	H38B—C38—H38C	109.5
C24—N6—C22	106.47 (13)	N2—C39—C40	113.60 (13)
C24—N6—C47	122.51 (13)	N2—C39—H39A	109.5 (11)
C22—N6—C47	125.80 (12)	C40—C39—H39A	111.9 (11)
C2—C1—S1	114.10 (14)	N2—C39—H39B	105.7 (11)
C2—C1—H1	123.0	C40—C39—H39B	107.9 (11)
S1—C1—H1	123.0	H39A—C39—H39B	107.9 (15)
C1—C2—C3	109.88 (17)	C39—C40—C41	112.63 (14)
C1—C2—H2	125.1	C39—C40—H40A	109.1
C3—C2—H2	125.1	C41—C40—H40A	109.1
C4—C3—N1	110.18 (15)	C39—C40—H40B	109.1
C4—C3—C2	114.69 (15)	C41—C40—H40B	109.1
N1—C3—C2	135.13 (16)	H40A—C40—H40B	107.8
C3—C4—C5	108.56 (14)	C40—C41—C42	113.17 (16)
C3—C4—S1	111.02 (13)	C40—C41—H41A	108.9
C5—C4—S1	140.42 (14)	C42—C41—H41A	108.9
C6—C5—C4	131.95 (15)	C40—C41—H41B	108.9
C6—C5—C12	122.48 (15)	C42—C41—H41B	108.9
C4—C5—C12	105.54 (14)	H41A—C41—H41B	107.8
C7—C6—C5	119.85 (15)	C41—C42—H42A	109.5
C7—C6—H6	120.1	C41—C42—H42B	109.5
C5—C6—H6	120.1	H42A—C42—H42B	109.5
C6—C7—C8	118.78 (15)	C41—C42—H42C	109.5
C6—C7—H7	120.6	H42A—C42—H42C	109.5
C8—C7—H7	120.6	H42B—C42—H42C	109.5
C7—C8—C11	122.94 (14)	N6—C47—C48	111.33 (13)
C7—C8—C9	130.32 (15)	N6—C47—H47A	109.4
C11—C8—C9	106.74 (13)	C48—C47—H47A	109.4
C10—C9—C13	119.73 (14)	N6—C47—H47B	109.4
C10—C9—C8	107.74 (13)	C48—C47—H47B	109.4
C13—C9—C8	132.50 (14)	H47A—C47—H47B	108.0
C9—C10—N2	109.83 (13)	C49—C48—C47	114.69 (13)
C9—C10—C16	120.72 (14)	C49—C48—H48A	108.6
N2—C10—C16	129.38 (13)	C47—C48—H48A	108.6
C8—C11—C12	118.30 (14)	C49—C48—H48B	108.6
C8—C11—N2	108.73 (13)	C47—C48—H48B	108.6
C12—C11—N2	132.88 (14)	H48A—C48—H48B	107.6
N1—C12—C11	133.98 (14)	C48—C49—C50	114.11 (14)
N1—C12—C5	108.60 (13)	C48—C49—H49A	108.7
C11—C12—C5	117.41 (14)	C50—C49—H49A	108.7
N3—C13—C9	127.21 (14)	C48—C49—H49B	108.7
N3—C13—C14	113.25 (14)	C50—C49—H49B	108.7
C9—C13—C14	119.53 (13)	H49A—C49—H49B	107.6
N4—C14—C15	126.76 (14)	C51—C50—C49	113.66 (14)
N4—C14—C13	113.64 (14)	C51—C50—H50A	108.8
C15—C14—C13	119.53 (14)	C49—C50—H50A	108.8
C16—C15—C14	119.81 (14)	C51—C50—H50B	108.8
C16—C15—C18	107.92 (13)	C49—C50—H50B	108.8
C14—C15—C18	132.18 (14)	H50A—C50—H50B	107.7
C15—C16—N5	110.08 (13)	C52—C51—C50	113.60 (14)
C15—C16—C10	120.55 (13)	C52—C51—H51A	108.8
N5—C16—C10	129.34 (14)	C50—C51—H51A	108.8
C18—C17—C22	119.32 (13)	C52—C51—H51B	108.8
C18—C17—N5	110.85 (13)	C50—C51—H51B	108.8
C22—C17—N5	129.83 (14)	H51A—C51—H51B	107.7
C17—C18—C19	122.17 (14)	C51—C52—C53	113.37 (14)
C17—C18—C15	105.73 (13)	C51—C52—H52A	108.9
C19—C18—C15	131.92 (14)	C53—C52—H52A	108.9
C20—C19—C18	118.62 (14)	C51—C52—H52B	108.9
C20—C19—H19	120.7	C53—C52—H52B	108.9
C18—C19—H19	120.7	H52A—C52—H52B	107.7
C19—C20—C21	119.71 (14)	C54—C53—C52	113.63 (15)
C19—C20—H20	120.1	C54—C53—H53A	108.8
C21—C20—H20	120.1	C52—C53—H53A	108.8
C20—C21—C22	122.02 (14)	C54—C53—H53B	108.8
C20—C21—C23	133.48 (14)	C52—C53—H53B	108.8
C22—C21—C23	104.49 (13)	H53A—C53—H53B	107.7
N6—C22—C17	131.94 (14)	C53—C54—C55	113.54 (15)
N6—C22—C21	110.54 (13)	C53—C54—H54A	108.9
C17—C22—C21	117.51 (14)	C55—C54—H54A	108.9
C24—C23—C21	108.69 (13)	C53—C54—H54B	108.9
C24—C23—S3	111.01 (12)	C55—C54—H54B	108.9
C21—C23—S3	139.99 (13)	H54A—C54—H54B	107.7
C23—C24—N6	109.78 (14)	C56—C55—C54	114.26 (16)
C23—C24—C25	114.03 (14)	C56—C55—H55A	108.7
N6—C24—C25	136.07 (15)	C54—C55—H55A	108.7
C26—C25—C24	110.38 (16)	C56—C55—H55B	108.7
C26—C25—H25	124.8	C54—C55—H55B	108.7
C24—C25—H25	124.8	H55A—C55—H55B	107.6
C25—C26—S3	113.72 (13)	C57—C56—C55	113.71 (18)
C25—C26—H26	123.1	C57—C56—H56A	108.8
S3—C26—H26	123.1	C55—C56—H56A	108.8
N1—C27—C28	113.59 (14)	C57—C56—H56B	108.8
N1—C27—H27A	106.0 (11)	C55—C56—H56B	108.8
C28—C27—H27A	108.3 (11)	H56A—C56—H56B	107.7
N1—C27—H27B	110.7 (12)	C58—C57—C56	113.1 (2)
C28—C27—H27B	111.0 (12)	C58—C57—H57A	109.0
H27A—C27—H27B	106.8 (16)	C56—C57—H57A	109.0
C29—C28—C27	112.44 (14)	C58—C57—H57B	109.0
C29—C28—H28A	109.1	C56—C57—H57B	109.0
C27—C28—H28A	109.1	H57A—C57—H57B	107.8
C29—C28—H28B	109.1	C57—C58—H58A	109.5
C27—C28—H28B	109.1	C57—C58—H58B	109.5
H28A—C28—H28B	107.8	H58A—C58—H58B	109.5
C28—C29—C30	115.06 (15)	C57—C58—H58C	109.5
C28—C29—H29A	108.5	H58A—C58—H58C	109.5
C30—C29—H29A	108.5	H58B—C58—H58C	109.5
C28—C29—H29B	108.5	C45B—C44B—C43	113.2 (3)
C30—C29—H29B	108.5	C45B—C44B—H44A	108.9
H29A—C29—H29B	107.5	C43—C44B—H44A	108.9
C29—C30—C31	116.34 (16)	C45B—C44B—H44B	108.9
C29—C30—H30A	108.2	C43—C44B—H44B	108.9
C31—C30—H30A	108.2	H44A—C44B—H44B	107.8
C29—C30—H30B	108.2	C44B—C45B—C46B	114.7 (3)
C31—C30—H30B	108.2	C44B—C45B—H45A	108.6
H30A—C30—H30B	107.4	C46B—C45B—H45A	108.6
C32—C31—C30	111.77 (15)	C44B—C45B—H45B	108.6
C32—C31—H31A	109.3	C46B—C45B—H45B	108.6
C30—C31—H31A	109.3	H45A—C45B—H45B	107.6
C32—C31—H31B	109.3	C45A—C46A—H46A	109.5
C30—C31—H31B	109.3	C45A—C46A—H46B	109.5
H31A—C31—H31B	107.9	H46A—C46A—H46B	109.5
C33—C32—C31	116.22 (15)	C45A—C46A—H46C	109.5
C33—C32—H32A	108.2	H46A—C46A—H46C	109.5
C31—C32—H32A	108.2	H46B—C46A—H46C	109.5
C33—C32—H32B	108.2	C45B—C46B—H46D	109.5
C31—C32—H32B	108.2	C45B—C46B—H46E	109.5
H32A—C32—H32B	107.4	H46D—C46B—H46E	109.5
C32—C33—C34	112.25 (15)	C45B—C46B—H46F	109.5
C32—C33—H33A	109.2	H46D—C46B—H46F	109.5
C34—C33—H33A	109.2	H46E—C46B—H46F	109.5
C32—C33—H33B	109.2	C43—C44A—C45A	113.5 (4)
C34—C33—H33B	109.2	C43—C44A—H44C	108.9
H33A—C33—H33B	107.9	C45A—C44A—H44C	108.9
C35—C34—C33	115.61 (16)	C43—C44A—H44D	108.9
C35—C34—H34A	108.4	C45A—C44A—H44D	108.9
C33—C34—H34A	108.4	H44C—C44A—H44D	107.7
C35—C34—H34B	108.4	C46A—C45A—C44A	112.1 (5)
C33—C34—H34B	108.4	C46A—C45A—H45C	109.2
H34A—C34—H34B	107.4	C44A—C45A—H45C	109.2
C34—C35—C36	113.20 (16)	C46A—C45A—H45D	109.2
C34—C35—H35A	108.9	C44A—C45A—H45D	109.2
C36—C35—H35A	108.9	H45C—C45A—H45D	107.9
C34—C35—H35B	108.9	C44A—C43—N5	119.8 (3)
C36—C35—H35B	108.9	N5—C43—C44B	109.10 (17)
H35A—C35—H35B	107.8	N5—C43—H43A	109.9
C35—C36—C37	114.76 (16)	C44B—C43—H43A	109.9
C35—C36—H36A	108.6	N5—C43—H43B	109.9
C37—C36—H36A	108.6	C44B—C43—H43B	109.9
C35—C36—H36B	108.6	H43A—C43—H43B	108.3

N4—S2—N3—C13	−0.17 (13)	N2—C10—C16—N5	−2.3 (3)
N3—S2—N4—C14	0.02 (12)	C16—N5—C17—C18	3.97 (16)
C4—S1—C1—C2	−0.07 (16)	C43—N5—C17—C18	−125.69 (14)
S1—C1—C2—C3	−0.2 (2)	C16—N5—C17—C22	−176.91 (15)
C12—N1—C3—C4	0.30 (19)	C43—N5—C17—C22	53.4 (2)
C27—N1—C3—C4	166.87 (15)	C22—C17—C18—C19	−7.6 (2)
C12—N1—C3—C2	179.03 (19)	N5—C17—C18—C19	171.58 (13)
C27—N1—C3—C2	−14.4 (3)	C22—C17—C18—C15	176.70 (13)
C1—C2—C3—C4	0.5 (2)	N5—C17—C18—C15	−4.08 (17)
C1—C2—C3—N1	−178.23 (19)	C16—C15—C18—C17	2.56 (17)
N1—C3—C4—C5	−0.9 (2)	C14—C15—C18—C17	178.84 (16)
C2—C3—C4—C5	−179.91 (15)	C16—C15—C18—C19	−172.50 (16)
N1—C3—C4—S1	178.50 (11)	C14—C15—C18—C19	3.8 (3)
C2—C3—C4—S1	−0.5 (2)	C17—C18—C19—C20	0.8 (2)
C1—S1—C4—C3	0.33 (14)	C15—C18—C19—C20	175.14 (16)
C1—S1—C4—C5	179.4 (2)	C18—C19—C20—C21	5.0 (2)
C3—C4—C5—C6	−177.05 (18)	C19—C20—C21—C22	−4.0 (2)
S1—C4—C5—C6	3.8 (3)	C19—C20—C21—C23	174.53 (16)
C3—C4—C5—C12	1.11 (19)	C24—N6—C22—C17	−179.15 (16)
S1—C4—C5—C12	−178.00 (17)	C47—N6—C22—C17	26.1 (3)
C4—C5—C6—C7	176.68 (18)	C24—N6—C22—C21	−0.37 (17)
C12—C5—C6—C7	−1.2 (3)	C47—N6—C22—C21	−155.07 (14)
C5—C6—C7—C8	2.7 (3)	C18—C17—C22—N6	−172.91 (15)
C6—C7—C8—C11	0.1 (3)	N5—C17—C22—N6	8.0 (3)
C6—C7—C8—C9	−179.22 (17)	C18—C17—C22—C21	8.4 (2)
C7—C8—C9—C10	179.83 (17)	N5—C17—C22—C21	−170.68 (14)
C11—C8—C9—C10	0.46 (17)	C20—C21—C22—N6	178.24 (14)
C7—C8—C9—C13	1.7 (3)	C23—C21—C22—N6	−0.68 (17)
C11—C8—C9—C13	−177.70 (16)	C20—C21—C22—C17	−2.8 (2)
C13—C9—C10—N2	179.50 (13)	C23—C21—C22—C17	178.30 (13)
C8—C9—C10—N2	1.06 (17)	C20—C21—C23—C24	−177.25 (17)
C13—C9—C10—C16	2.2 (2)	C22—C21—C23—C24	1.49 (17)
C8—C9—C10—C16	−176.21 (14)	C20—C21—C23—S3	−4.5 (3)
C11—N2—C10—C9	−2.16 (17)	C22—C21—C23—S3	174.20 (15)
C39—N2—C10—C9	145.58 (14)	C26—S3—C23—C24	0.05 (13)
C11—N2—C10—C16	174.80 (15)	C26—S3—C23—C21	−172.55 (19)
C39—N2—C10—C16	−37.5 (2)	C21—C23—C24—N6	−1.80 (18)
C7—C8—C11—C12	−4.3 (2)	S3—C23—C24—N6	−176.78 (11)
C9—C8—C11—C12	175.12 (14)	C21—C23—C24—C25	174.80 (14)
C7—C8—C11—N2	178.79 (15)	S3—C23—C24—C25	−0.18 (18)
C9—C8—C11—N2	−1.79 (17)	C22—N6—C24—C23	1.34 (17)
C10—N2—C11—C8	2.43 (17)	C47—N6—C24—C23	157.07 (14)
C39—N2—C11—C8	−143.31 (15)	C22—N6—C24—C25	−174.18 (18)
C10—N2—C11—C12	−173.86 (16)	C47—N6—C24—C25	−18.4 (3)
C39—N2—C11—C12	40.4 (3)	C23—C24—C25—C26	0.3 (2)
C3—N1—C12—C11	−179.01 (17)	N6—C24—C25—C26	175.64 (18)
C27—N1—C12—C11	15.9 (3)	C24—C25—C26—S3	−0.22 (19)
C3—N1—C12—C5	0.41 (17)	C23—S3—C26—C25	0.11 (14)
C27—N1—C12—C5	−164.63 (16)	C3—N1—C27—C28	−99.21 (17)
C8—C11—C12—N1	−175.07 (16)	C12—N1—C27—C28	64.0 (2)
N2—C11—C12—N1	0.9 (3)	N1—C27—C28—C29	73.04 (18)
C8—C11—C12—C5	5.5 (2)	C27—C28—C29—C30	−169.09 (15)
N2—C11—C12—C5	−178.45 (16)	C28—C29—C30—C31	−69.4 (2)
C6—C5—C12—N1	177.45 (15)	C29—C30—C31—C32	178.87 (16)
C4—C5—C12—N1	−0.93 (18)	C30—C31—C32—C33	−178.71 (16)
C6—C5—C12—C11	−3.0 (2)	C31—C32—C33—C34	176.20 (16)
C4—C5—C12—C11	178.60 (14)	C32—C33—C34—C35	178.09 (16)
S2—N3—C13—C9	−179.74 (13)	C33—C34—C35—C36	176.45 (16)
S2—N3—C13—C14	0.26 (16)	C34—C35—C36—C37	−179.51 (16)
C10—C9—C13—N3	−179.01 (15)	C35—C36—C37—C38	−173.54 (17)
C8—C9—C13—N3	−1.0 (3)	C10—N2—C39—C40	−101.39 (16)
C10—C9—C13—C14	1.0 (2)	C11—N2—C39—C40	40.4 (2)
C8—C9—C13—C14	178.98 (16)	N2—C39—C40—C41	63.64 (18)
S2—N4—C14—C15	−176.72 (13)	C39—C40—C41—C42	166.20 (14)
S2—N4—C14—C13	0.13 (16)	C24—N6—C47—C48	72.22 (18)
N3—C13—C14—N4	−0.3 (2)	C22—N6—C47—C48	−136.85 (15)
C9—C13—C14—N4	179.73 (14)	N6—C47—C48—C49	169.53 (13)
N3—C13—C14—C15	176.84 (14)	C47—C48—C49—C50	−68.98 (19)
C9—C13—C14—C15	−3.2 (2)	C48—C49—C50—C51	−163.97 (14)
N4—C14—C15—C16	178.79 (15)	C49—C50—C51—C52	179.36 (15)
C13—C14—C15—C16	2.1 (2)	C50—C51—C52—C53	−173.67 (15)
N4—C14—C15—C18	2.9 (3)	C51—C52—C53—C54	178.37 (16)
C13—C14—C15—C18	−173.82 (15)	C52—C53—C54—C55	−179.46 (16)
C14—C15—C16—N5	−176.99 (13)	C53—C54—C55—C56	−176.66 (17)
C18—C15—C16—N5	−0.17 (17)	C54—C55—C56—C57	−177.76 (17)
C14—C15—C16—C10	1.1 (2)	C55—C56—C57—C58	−176.72 (19)
C18—C15—C16—C10	177.93 (13)	C43—C44B—C45B—C46B	−64.9 (4)
C17—N5—C16—C15	−2.26 (16)	C43—C44A—C45A—C46A	−169.8 (6)
C43—N5—C16—C15	125.87 (14)	C45A—C44A—C43—N5	−179.7 (3)
C17—N5—C16—C10	179.85 (15)	C16—N5—C43—C44A	−36.5 (4)
C43—N5—C16—C10	−52.0 (2)	C17—N5—C43—C44A	87.1 (4)
C9—C10—C16—C15	−3.3 (2)	C16—N5—C43—C44B	−62.8 (2)
N2—C10—C16—C15	179.98 (15)	C17—N5—C43—C44B	60.8 (2)
C9—C10—C16—N5	174.35 (15)	C45B—C44B—C43—N5	−172.0 (2)

Parameters (Å, °) of π–π and C—H···π interactions in the solid of TIP top

Interactions for rings of A, B, C, D and E are calculated for the atom sequences S1—C1—C2—C3—C4, N6—C22—C21—C23—C24, S3—C23—C21—C20—C19—C18—C17—C22—N6—C24—C25—C26, S3—C23—C24—C25—C26 and S3—C23—C21—C22—N6—C24—C25—C26, respectively.

Interaction	Distance	Angle
Ring A(π)···Ring A(π)	3.509 (2)^a	0(1)^c
	3.450 (2)^b
C19—H19···Ring B(π)	3.502 (2)^d	121 (1)^e	40 (1)^f
C19—H19···Ring C(π)	3.577 (2)^d	128 (1)^e	40 (1)^f
C20—H20···Ring D(π)	3.361 (2)^d	143 (1)^e	49 (1)^f
C20—H20···Ring E(π)	3.318 (2)^d	127 (1)^e	48 (1)^f

Notes: (a) distance between ring centroids; (b) perpendicular distance between rings; (c) dihedral angle between planes; a (d) carbon–centroid distance; (e) angle of carbon–hydrogen–centroid; (f) angle of carbon–hydrogen–π.

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Synthesis and properties of a novel deca­cyclic S,N-hetero­acene

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Synthesis and properties of a novel decacyclic S,N-heteroacene