(E)-2-[1-(1-Benzothio-phen-2-yl)ethyl-idene]-N-phenyl-hydrazinecarboxamide.

The title compound, C(17)H(15)N(3)OS, crystallizes with two unique mol-ecules, denoted 1 and 2, in the asymmetric unit. The two mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both mol-ecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothio-phene groups and N-bound phenyl rings are 36.36 (9)° for mol-ecule 1 and 29.71 (9)° for mol-ecule 2. The C=N-NH-C(O)NH ethyl-idene-hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 Å, respectively, for the two mol-ecules. The methyl substituents lie 0.338 (3) and 0.396 (3) Å, respectively, from these planes. The C=N-NH-C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)°, respectively, in mol-ecules 1 and 2. This conformation is enhanced by weak intra-molecular C-H⋯O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each mol-ecule. In the crystal, pairs of mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds into dimers. Alternating dimers are further inter-connected by weak C-H⋯O contacts into zigzag rows along b. The rows are stacked along a by C-H⋯π contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothio-phene units.

Related literature

For background to the biological activity of semicarbazones, see: Alam et al. (2010 ▶); Sharma et al. (2006 ▶); Siji et al. (2010 ▶); Sriram et al. (2004 ▶). For related structures, see: Beraldo et al. (2001 ▶); Fun et al. (2009a ▶,b ▶); Mendoza-Meroño et al. (2011 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H15N3OS

M = 309.38

Triclinic,

a = 9.8858 (3) Å

b = 13.2737 (5) Å

c = 13.6121 (8) Å

α = 113.961 (3)°

β = 98.153 (3)°

γ = 107.778 (2)°

V = 1480.02 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 89 K

0.38 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.826, T max = 1.000

25263 measured reflections

8650 independent reflections

5747 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.147

S = 1.07

8650 reflections

411 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037457/tk2786sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037457/tk2786Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037457/tk2786Isup3.cml

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

C17H15N3OS	Z = 4
Mr = 309.38	F(000) = 648
Triclinic, P1	Dx = 1.388 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8858 (3) Å	Cell parameters from 3121 reflections
b = 13.2737 (5) Å	θ = 2.3–24.7°
c = 13.6121 (8) Å	µ = 0.22 mm−1
α = 113.961 (3)°	T = 89 K
β = 98.153 (3)°	Rectangular plate, colourless
γ = 107.778 (2)°	0.38 × 0.14 × 0.05 mm
V = 1480.02 (11) Å3

Bruker APEXII CCD area-detector diffractometer	8650 independent reflections
Radiation source: fine-focus sealed tube	5747 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.826, Tmax = 1.000	k = −18→18
25263 measured reflections	l = −19→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3
8650 reflections	(Δ/σ)max < 0.001
411 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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
S11	0.31292 (6)	1.02673 (4)	0.78076 (4)	0.02141 (13)
C11	0.2261 (2)	0.93460 (17)	0.63600 (16)	0.0182 (4)
C12	0.1846 (2)	0.99340 (18)	0.58266 (17)	0.0199 (4)
H12	0.1351	0.9563	0.5041	0.024*
C13	0.2253 (2)	1.11904 (17)	0.66052 (16)	0.0180 (4)
C14	0.2057 (2)	1.20934 (18)	0.63901 (18)	0.0223 (4)
H14	0.1568	1.1906	0.5647	0.027*
C15	0.2576 (2)	1.32550 (19)	0.72612 (18)	0.0251 (5)
H15	0.2451	1.3866	0.7112	0.030*
C16	0.3287 (2)	1.35423 (18)	0.83629 (18)	0.0240 (4)
H16	0.3640	1.4347	0.8951	0.029*
C17	0.3481 (2)	1.26718 (18)	0.86079 (17)	0.0221 (4)
H17	0.3952	1.2866	0.9358	0.027*
C18	0.2966 (2)	1.14948 (18)	0.77204 (17)	0.0201 (4)
C19	0.2066 (2)	0.80832 (17)	0.58560 (16)	0.0181 (4)
C110	0.1043 (2)	0.72127 (18)	0.46823 (16)	0.0237 (4)
H11A	0.1562	0.6766	0.4240	0.035*
H11B	0.0740	0.7653	0.4328	0.035*
H11C	0.0157	0.6649	0.4710	0.035*
N11	0.28160 (17)	0.78150 (14)	0.64940 (13)	0.0190 (3)
N12	0.26205 (18)	0.66309 (15)	0.60819 (14)	0.0200 (4)
H12N	0.193 (2)	0.6052 (19)	0.5336 (18)	0.024*
C111	0.3580 (2)	0.63400 (17)	0.66381 (16)	0.0189 (4)
O11	0.34514 (15)	0.52858 (12)	0.62557 (11)	0.0231 (3)
N13	0.46505 (19)	0.72820 (15)	0.75850 (14)	0.0212 (4)
H13N	0.460 (2)	0.798 (2)	0.7734 (18)	0.025*
C112	0.5902 (2)	0.72786 (18)	0.82322 (16)	0.0200 (4)
C113	0.6083 (2)	0.62516 (19)	0.81270 (19)	0.0298 (5)
H113	0.5327	0.5479	0.7611	0.036*
C114	0.7391 (3)	0.6363 (2)	0.8788 (2)	0.0356 (6)
H114	0.7524	0.5656	0.8703	0.043*
C115	0.8490 (2)	0.74708 (19)	0.95598 (17)	0.0246 (4)
H115	0.9372	0.7532	1.0007	0.030*
C116	0.8291 (2)	0.84825 (19)	0.96713 (17)	0.0277 (5)
H116	0.9038	0.9253	1.0205	0.033*
C117	0.7008 (2)	0.83968 (19)	0.90140 (18)	0.0300 (5)
H117	0.6887	0.9108	0.9100	0.036*
S21	0.10557 (5)	−0.03449 (5)	0.26492 (4)	0.02144 (13)
C21	0.2802 (2)	0.07844 (17)	0.35461 (15)	0.0183 (4)
C22	0.3828 (2)	0.03329 (17)	0.37642 (16)	0.0172 (4)
H22	0.4829	0.0820	0.4238	0.021*
C23	0.3203 (2)	−0.09632 (18)	0.31879 (16)	0.0195 (4)
C24	0.3903 (2)	−0.17387 (18)	0.31967 (17)	0.0229 (4)
H24	0.4920	−0.1417	0.3625	0.027*
C25	0.3106 (2)	−0.29689 (19)	0.25799 (17)	0.0248 (4)
H25	0.3577	−0.3494	0.2583	0.030*
C26	0.1598 (2)	−0.34491 (19)	0.19454 (17)	0.0247 (4)
H26	0.1062	−0.4297	0.1523	0.030*
C27	0.0886 (2)	−0.27078 (18)	0.19275 (17)	0.0233 (4)
H27	−0.0134	−0.3038	0.1502	0.028*
C28	0.1692 (2)	−0.14626 (18)	0.25469 (16)	0.0193 (4)
C29	0.3002 (2)	0.20465 (18)	0.40077 (16)	0.0191 (4)
C210	0.4392 (2)	0.30265 (18)	0.49234 (16)	0.0228 (4)
H21A	0.4728	0.3703	0.4764	0.034*
H21B	0.5173	0.2720	0.4956	0.034*
H21C	0.4186	0.3298	0.5649	0.034*
N21	0.18945 (18)	0.22163 (14)	0.35750 (13)	0.0202 (4)
N22	0.19800 (19)	0.33747 (15)	0.40139 (14)	0.0225 (4)
H22N	0.261 (2)	0.388 (2)	0.4711 (19)	0.027*
C211	0.0935 (2)	0.36293 (18)	0.34891 (16)	0.0207 (4)
O21	0.09507 (17)	0.46410 (13)	0.38988 (12)	0.0291 (4)
N23	−0.00679 (18)	0.26752 (15)	0.25064 (14)	0.0203 (4)
H23N	0.005 (2)	0.201 (2)	0.2342 (18)	0.024*
C212	−0.1117 (2)	0.26998 (18)	0.17048 (16)	0.0198 (4)
C213	−0.1193 (2)	0.37503 (19)	0.17685 (17)	0.0238 (4)
H213	−0.0578	0.4508	0.2406	0.029*
C214	−0.2185 (2)	0.3675 (2)	0.08827 (18)	0.0287 (5)
H214	−0.2228	0.4393	0.0915	0.034*
C215	−0.3112 (2)	0.25807 (19)	−0.00446 (17)	0.0254 (5)
H215	−0.3781	0.2544	−0.0645	0.030*
C216	−0.3048 (2)	0.15487 (19)	−0.00818 (18)	0.0297 (5)
H216	−0.3685	0.0791	−0.0711	0.036*
C217	−0.2063 (2)	0.15971 (19)	0.07875 (17)	0.0270 (5)
H217	−0.2038	0.0875	0.0755	0.032*

	U11	U22	U33	U12	U13	U23
S11	0.0247 (3)	0.0198 (3)	0.0174 (3)	0.0095 (2)	0.0014 (2)	0.0079 (2)
C11	0.0149 (9)	0.0197 (10)	0.0162 (10)	0.0056 (8)	0.0016 (7)	0.0072 (8)
C12	0.0156 (9)	0.0264 (11)	0.0246 (11)	0.0092 (8)	0.0068 (8)	0.0175 (9)
C13	0.0146 (9)	0.0204 (10)	0.0204 (10)	0.0076 (8)	0.0056 (7)	0.0106 (8)
C14	0.0181 (9)	0.0284 (11)	0.0273 (11)	0.0108 (9)	0.0081 (8)	0.0181 (10)
C15	0.0233 (10)	0.0234 (11)	0.0344 (12)	0.0106 (9)	0.0091 (9)	0.0179 (10)
C16	0.0242 (10)	0.0192 (10)	0.0279 (11)	0.0118 (9)	0.0076 (9)	0.0085 (9)
C17	0.0208 (10)	0.0242 (11)	0.0217 (10)	0.0107 (9)	0.0064 (8)	0.0101 (9)
C18	0.0179 (9)	0.0236 (10)	0.0217 (10)	0.0097 (8)	0.0053 (8)	0.0126 (9)
C19	0.0161 (9)	0.0199 (10)	0.0166 (9)	0.0067 (8)	0.0057 (7)	0.0072 (8)
C110	0.0255 (10)	0.0209 (10)	0.0196 (10)	0.0084 (9)	0.0013 (8)	0.0077 (9)
N11	0.0190 (8)	0.0154 (8)	0.0192 (8)	0.0058 (7)	0.0046 (7)	0.0065 (7)
N12	0.0219 (9)	0.0159 (8)	0.0167 (8)	0.0064 (7)	0.0006 (7)	0.0054 (7)
C111	0.0181 (9)	0.0190 (10)	0.0142 (9)	0.0046 (8)	0.0008 (7)	0.0066 (8)
O11	0.0287 (8)	0.0139 (7)	0.0172 (7)	0.0068 (6)	−0.0029 (6)	0.0035 (6)
N13	0.0250 (9)	0.0142 (8)	0.0180 (9)	0.0091 (7)	−0.0022 (7)	0.0039 (7)
C112	0.0215 (10)	0.0221 (10)	0.0132 (9)	0.0091 (8)	0.0020 (8)	0.0063 (8)
C113	0.0295 (12)	0.0174 (10)	0.0288 (12)	0.0068 (9)	−0.0057 (9)	0.0055 (9)
C114	0.0383 (13)	0.0270 (12)	0.0319 (13)	0.0187 (11)	−0.0051 (10)	0.0064 (10)
C115	0.0231 (10)	0.0307 (12)	0.0180 (10)	0.0124 (9)	0.0029 (8)	0.0097 (9)
C116	0.0242 (11)	0.0255 (11)	0.0193 (11)	0.0023 (9)	−0.0041 (8)	0.0070 (9)
C117	0.0320 (12)	0.0183 (11)	0.0265 (12)	0.0069 (9)	−0.0064 (9)	0.0061 (9)
S21	0.0167 (2)	0.0221 (3)	0.0208 (3)	0.0069 (2)	0.00048 (19)	0.0083 (2)
C21	0.0158 (9)	0.0215 (10)	0.0134 (9)	0.0058 (8)	0.0021 (7)	0.0066 (8)
C22	0.0146 (9)	0.0168 (9)	0.0165 (9)	0.0046 (7)	0.0052 (7)	0.0057 (8)
C23	0.0162 (9)	0.0224 (10)	0.0168 (10)	0.0068 (8)	0.0037 (7)	0.0076 (8)
C24	0.0168 (9)	0.0274 (11)	0.0228 (11)	0.0101 (9)	0.0051 (8)	0.0099 (9)
C25	0.0256 (11)	0.0264 (11)	0.0251 (11)	0.0152 (9)	0.0074 (9)	0.0113 (9)
C26	0.0244 (11)	0.0212 (11)	0.0223 (11)	0.0063 (9)	0.0053 (8)	0.0075 (9)
C27	0.0216 (10)	0.0245 (11)	0.0188 (10)	0.0067 (9)	0.0019 (8)	0.0090 (9)
C28	0.0192 (9)	0.0231 (10)	0.0154 (9)	0.0088 (8)	0.0046 (8)	0.0088 (8)
C29	0.0190 (9)	0.0234 (10)	0.0173 (10)	0.0095 (8)	0.0078 (8)	0.0104 (8)
C210	0.0207 (10)	0.0242 (11)	0.0179 (10)	0.0072 (9)	0.0030 (8)	0.0075 (9)
N21	0.0248 (9)	0.0180 (8)	0.0154 (8)	0.0088 (7)	0.0044 (7)	0.0061 (7)
N22	0.0244 (9)	0.0187 (9)	0.0146 (8)	0.0083 (7)	−0.0023 (7)	0.0019 (7)
C211	0.0213 (10)	0.0197 (10)	0.0152 (10)	0.0059 (8)	0.0009 (8)	0.0062 (8)
O21	0.0336 (9)	0.0218 (8)	0.0188 (8)	0.0127 (7)	−0.0054 (6)	0.0009 (6)
N23	0.0224 (8)	0.0167 (8)	0.0165 (9)	0.0082 (7)	−0.0003 (7)	0.0049 (7)
C212	0.0189 (9)	0.0213 (10)	0.0160 (10)	0.0064 (8)	0.0021 (8)	0.0081 (8)
C213	0.0245 (10)	0.0223 (11)	0.0197 (10)	0.0087 (9)	0.0012 (8)	0.0079 (9)
C214	0.0308 (12)	0.0301 (12)	0.0303 (12)	0.0173 (10)	0.0054 (10)	0.0166 (10)
C215	0.0237 (10)	0.0325 (12)	0.0194 (10)	0.0127 (9)	0.0021 (8)	0.0123 (9)
C216	0.0280 (11)	0.0238 (12)	0.0215 (11)	0.0049 (9)	−0.0059 (9)	0.0050 (9)
C217	0.0295 (11)	0.0203 (11)	0.0220 (11)	0.0068 (9)	−0.0027 (9)	0.0077 (9)

S11—C18	1.734 (2)	S21—C28	1.745 (2)
S11—C11	1.7427 (19)	S21—C21	1.7473 (19)
C11—C12	1.369 (2)	C21—C22	1.381 (2)
C11—C19	1.466 (3)	C21—C29	1.466 (3)
C12—C13	1.449 (3)	C22—C23	1.440 (3)
C12—H12	0.9500	C22—H22	0.9500
C13—C14	1.404 (3)	C23—C24	1.407 (3)
C13—C18	1.410 (3)	C23—C28	1.410 (3)
C14—C15	1.380 (3)	C24—C25	1.380 (3)
C14—H14	0.9500	C24—H24	0.9500
C15—C16	1.400 (3)	C25—C26	1.408 (3)
C15—H15	0.9500	C25—H25	0.9500
C16—C17	1.383 (3)	C26—C27	1.379 (3)
C16—H16	0.9500	C26—H26	0.9500
C17—C18	1.402 (3)	C27—C28	1.397 (3)
C17—H17	0.9500	C27—H27	0.9500
C19—N11	1.289 (2)	C29—N21	1.293 (2)
C19—C110	1.496 (3)	C29—C210	1.497 (3)
C110—H11A	0.9800	C210—H21A	0.9800
C110—H11B	0.9800	C210—H21B	0.9800
C110—H11C	0.9800	C210—H21C	0.9800
N11—N12	1.375 (2)	N21—N22	1.374 (2)
N12—C111	1.371 (2)	N22—C211	1.376 (2)
N12—H12N	0.97 (2)	N22—H22N	0.89 (2)
C111—O11	1.235 (2)	C211—O21	1.221 (2)
C111—N13	1.357 (2)	C211—N23	1.363 (2)
N13—C112	1.416 (2)	N23—C212	1.413 (2)
N13—H13N	0.89 (2)	N23—H23N	0.87 (2)
C112—C113	1.382 (3)	C212—C217	1.387 (3)
C112—C117	1.388 (3)	C212—C213	1.388 (3)
C113—C114	1.396 (3)	C213—C214	1.390 (3)
C113—H113	0.9500	C213—H213	0.9500
C114—C115	1.376 (3)	C214—C215	1.383 (3)
C114—H114	0.9500	C214—H214	0.9500
C115—C116	1.368 (3)	C215—C216	1.372 (3)
C115—H115	0.9500	C215—H215	0.9500
C116—C117	1.389 (3)	C216—C217	1.387 (3)
C116—H116	0.9500	C216—H216	0.9500
C117—H117	0.9500	C217—H217	0.9500
C18—S11—C11	91.28 (9)	C28—S21—C21	91.28 (9)
C12—C11—C19	127.84 (18)	C22—C21—C29	128.03 (17)
C12—C11—S11	113.22 (15)	C22—C21—S21	112.81 (14)
C19—C11—S11	118.94 (14)	C29—C21—S21	119.10 (14)
C11—C12—C13	111.86 (18)	C21—C22—C23	112.03 (17)
C11—C12—H12	124.1	C21—C22—H22	124.0
C13—C12—H12	124.1	C23—C22—H22	124.0
C14—C13—C18	118.69 (18)	C24—C23—C28	119.07 (18)
C14—C13—C12	129.36 (18)	C24—C23—C22	128.48 (18)
C18—C13—C12	111.93 (17)	C28—C23—C22	112.45 (17)
C15—C14—C13	119.85 (19)	C25—C24—C23	119.75 (18)
C15—C14—H14	120.1	C25—C24—H24	120.1
C13—C14—H14	120.1	C23—C24—H24	120.1
C14—C15—C16	120.69 (19)	C24—C25—C26	120.27 (19)
C14—C15—H15	119.7	C24—C25—H25	119.9
C16—C15—H15	119.7	C26—C25—H25	119.9
C17—C16—C15	121.00 (19)	C27—C26—C25	121.06 (19)
C17—C16—H16	119.5	C27—C26—H26	119.5
C15—C16—H16	119.5	C25—C26—H26	119.5
C16—C17—C18	118.25 (19)	C26—C27—C28	118.75 (18)
C16—C17—H17	120.9	C26—C27—H27	120.6
C18—C17—H17	120.9	C28—C27—H27	120.6
C17—C18—C13	121.51 (18)	C27—C28—C23	121.10 (18)
C17—C18—S11	126.77 (15)	C27—C28—S21	127.46 (15)
C13—C18—S11	111.71 (15)	C23—C28—S21	111.44 (15)
N11—C19—C11	115.21 (17)	N21—C29—C21	114.78 (17)
N11—C19—C110	124.97 (18)	N21—C29—C210	124.63 (18)
C11—C19—C110	119.82 (16)	C21—C29—C210	120.58 (17)
C19—C110—H11A	109.5	C29—C210—H21A	109.5
C19—C110—H11B	109.5	C29—C210—H21B	109.5
H11A—C110—H11B	109.5	H21A—C210—H21B	109.5
C19—C110—H11C	109.5	C29—C210—H21C	109.5
H11A—C110—H11C	109.5	H21A—C210—H21C	109.5
H11B—C110—H11C	109.5	H21B—C210—H21C	109.5
C19—N11—N12	117.57 (16)	C29—N21—N22	117.60 (16)
C111—N12—N11	119.32 (16)	N21—N22—C211	119.89 (16)
C111—N12—H12N	121.2 (13)	N21—N22—H22N	115.3 (14)
N11—N12—H12N	118.4 (13)	C211—N22—H22N	123.5 (14)
O11—C111—N13	124.78 (17)	O21—C211—N23	124.92 (18)
O11—C111—N12	120.06 (17)	O21—C211—N22	120.69 (18)
N13—C111—N12	115.14 (17)	N23—C211—N22	114.39 (18)
C111—N13—C112	127.34 (17)	C211—N23—C212	127.10 (17)
C111—N13—H13N	113.6 (14)	C211—N23—H23N	113.9 (14)
C112—N13—H13N	118.4 (14)	C212—N23—H23N	118.6 (14)
C113—C112—C117	119.18 (18)	C217—C212—C213	119.81 (18)
C113—C112—N13	124.47 (18)	C217—C212—N23	116.38 (18)
C117—C112—N13	116.35 (18)	C213—C212—N23	123.75 (18)
C112—C113—C114	119.2 (2)	C212—C213—C214	118.85 (19)
C112—C113—H113	120.4	C212—C213—H213	120.6
C114—C113—H113	120.4	C214—C213—H213	120.6
C115—C114—C113	121.6 (2)	C215—C214—C213	121.6 (2)
C115—C114—H114	119.2	C215—C214—H214	119.2
C113—C114—H114	119.2	C213—C214—H214	119.2
C116—C115—C114	118.76 (19)	C216—C215—C214	118.77 (19)
C116—C115—H115	120.6	C216—C215—H215	120.6
C114—C115—H115	120.6	C214—C215—H215	120.6
C115—C116—C117	120.8 (2)	C215—C216—C217	120.9 (2)
C115—C116—H116	119.6	C215—C216—H216	119.6
C117—C116—H116	119.6	C217—C216—H216	119.6
C112—C117—C116	120.4 (2)	C216—C217—C212	120.05 (19)
C112—C117—H117	119.8	C216—C217—H217	120.0
C116—C117—H117	119.8	C212—C217—H217	120.0
C18—S11—C11—C12	−0.58 (16)	C28—S21—C21—C22	−0.23 (15)
C18—S11—C11—C19	178.95 (16)	C28—S21—C21—C29	−177.63 (16)
C19—C11—C12—C13	−178.81 (18)	C29—C21—C22—C23	177.56 (18)
S11—C11—C12—C13	0.7 (2)	S21—C21—C22—C23	0.4 (2)
C11—C12—C13—C14	178.41 (19)	C21—C22—C23—C24	179.47 (19)
C11—C12—C13—C18	−0.4 (2)	C21—C22—C23—C28	−0.5 (2)
C18—C13—C14—C15	0.8 (3)	C28—C23—C24—C25	0.1 (3)
C12—C13—C14—C15	−177.90 (19)	C22—C23—C24—C25	−179.82 (19)
C13—C14—C15—C16	−0.6 (3)	C23—C24—C25—C26	−0.1 (3)
C14—C15—C16—C17	−0.2 (3)	C24—C25—C26—C27	−0.2 (3)
C15—C16—C17—C18	0.8 (3)	C25—C26—C27—C28	0.5 (3)
C16—C17—C18—C13	−0.6 (3)	C26—C27—C28—C23	−0.5 (3)
C16—C17—C18—S11	177.95 (15)	C26—C27—C28—S21	179.33 (15)
C14—C13—C18—C17	−0.2 (3)	C24—C23—C28—C27	0.2 (3)
C12—C13—C18—C17	178.72 (17)	C22—C23—C28—C27	−179.86 (17)
C14—C13—C18—S11	−178.98 (14)	C24—C23—C28—S21	−179.65 (15)
C12—C13—C18—S11	0.0 (2)	C22—C23—C28—S21	0.3 (2)
C11—S11—C18—C17	−178.33 (19)	C21—S21—C28—C27	−179.87 (19)
C11—S11—C18—C13	0.33 (15)	C21—S21—C28—C23	−0.05 (15)
C12—C11—C19—N11	166.45 (19)	C22—C21—C29—N21	173.78 (18)
S11—C11—C19—N11	−13.0 (2)	S21—C21—C29—N21	−9.3 (2)
C12—C11—C19—C110	−13.9 (3)	C22—C21—C29—C210	−7.3 (3)
S11—C11—C19—C110	166.64 (15)	S21—C21—C29—C210	169.70 (15)
C11—C19—N11—N12	177.05 (16)	C21—C29—N21—N22	176.63 (16)
C110—C19—N11—N12	−2.6 (3)	C210—C29—N21—N22	−2.3 (3)
C19—N11—N12—C111	168.46 (17)	C29—N21—N22—C211	171.23 (18)
N11—N12—C111—O11	−177.39 (17)	N21—N22—C211—O21	176.31 (18)
N11—N12—C111—N13	1.1 (3)	N21—N22—C211—N23	−4.0 (3)
O11—C111—N13—C112	8.0 (3)	O21—C211—N23—C212	9.9 (3)
N12—C111—N13—C112	−170.44 (18)	N22—C211—N23—C212	−169.85 (18)
C111—N13—C112—C113	−13.3 (3)	C211—N23—C212—C217	−177.5 (2)
C111—N13—C112—C117	166.3 (2)	C211—N23—C212—C213	5.4 (3)
C117—C112—C113—C114	−1.6 (3)	C217—C212—C213—C214	−2.5 (3)
N13—C112—C113—C114	177.9 (2)	N23—C212—C213—C214	174.54 (19)
C112—C113—C114—C115	1.4 (4)	C212—C213—C214—C215	1.3 (3)
C113—C114—C115—C116	−0.3 (4)	C213—C214—C215—C216	0.3 (3)
C114—C115—C116—C117	−0.4 (3)	C214—C215—C216—C217	−0.6 (3)
C113—C112—C117—C116	0.9 (3)	C215—C216—C217—C212	−0.7 (3)
N13—C112—C117—C116	−178.7 (2)	C213—C212—C217—C216	2.2 (3)
C115—C116—C117—C112	0.2 (3)	N23—C212—C217—C216	−175.0 (2)

Cg1 is the centroid of the S11, C11, C12, C13, C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12N···O21	0.97 (2)	1.91 (2)	2.847 (2)	162.1 (19)
N22—H22N···O11	0.89 (2)	1.99 (2)	2.840 (2)	158 (2)
C113—H113···O11	0.95	2.29	2.886 (2)	120.
C213—H213···O21	0.95	2.26	2.871 (2)	121.
C15—H15···O11i	0.95	2.62	3.435 (2)	144.
C24—H24···Cg1ii	0.95	2.80	3.482 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S11, C11, C12, C13, C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12N⋯O21	0.97 (2)	1.91 (2)	2.847 (2)	162.1 (19)
N22—H22N⋯O11	0.89 (2)	1.99 (2)	2.840 (2)	158 (2)
C113—H113⋯O11	0.95	2.29	2.886 (2)	120
C213—H213⋯O21	0.95	2.26	2.871 (2)	121
C15—H15⋯O11i	0.95	2.62	3.435 (2)	144
C24—H24⋯Cg1ii	0.95	2.80	3.482 (2)	130

Symmetry codes: (i) ; (ii) .