(E)-1,1-Diphenyl-2-(thio-phen-2-yl-methyl-idene)hydrazine.

The asymmetric unit of the title compound, C17H14N2S, consists of two crystallographically independent mol-ecules with similar conformations. The dihedral angles between the phenyl rings are 89.32 (5) and 82.80 (5)° in the two mol-ecules. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For biological applications of hydrazine derivatives, see: Vogel et al. (2008 ▶); Moreira et al. (2012 ▶); Vicini et al. (2009 ▶); Belkheiri et al. (2010 ▶); Shen et al. (2011 ▶).

Experimental

Crystal data

C17H14N2S

M = 278.36

Triclinic,

a = 9.8336 (11) Å

b = 9.8665 (9) Å

c = 16.6357 (8) Å

α = 100.290 (6)°

β = 101.696 (7)°

γ = 109.129 (9)°

V = 1439.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 144 K

0.58 × 0.51 × 0.36 mm

Data collection

Agilent Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▶) T min = 0.916, T max = 0.939

10771 measured reflections

5672 independent reflections

4856 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.07

5672 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033874/is5326sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033874/is5326Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033874/is5326Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H14N2S	Z = 4
Mr = 278.36	F(000) = 584
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8336 (11) Å	Cell parameters from 6444 reflections
b = 9.8665 (9) Å	θ = 3.6–26.0°
c = 16.6357 (8) Å	µ = 0.22 mm−1
α = 100.290 (6)°	T = 144 K
β = 101.696 (7)°	Prism, colourless
γ = 109.129 (9)°	0.58 × 0.51 × 0.36 mm
V = 1439.9 (2) Å3

Agilent Xcalibur (Atlas, Gemini) diffractometer	5672 independent reflections
Graphite monochromator	4856 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.020
ω scans	θmax = 26.1°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −12→12
Tmin = 0.916, Tmax = 0.939	k = −10→12
10771 measured reflections	l = −20→20

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0382P)2 + 0.4189P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.23 e Å−3
5672 reflections	Δρmin = −0.33 e Å−3
361 parameters

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.

	x	y	z	Uiso*/Ueq
S1A	0.45980 (5)	0.49688 (5)	0.64718 (3)	0.03525 (13)
N1A	0.22725 (17)	0.04849 (15)	0.46812 (8)	0.0294 (3)
N2A	0.29506 (15)	0.18305 (15)	0.52848 (8)	0.0258 (3)
C1A	0.14928 (18)	0.05017 (18)	0.38736 (10)	0.0230 (3)
C2A	0.17908 (19)	0.18184 (19)	0.36238 (11)	0.0277 (4)
H2A	0.2535	0.272	0.3995	0.033*
C3A	0.0996 (2)	0.1807 (2)	0.28310 (11)	0.0333 (4)
H3A	0.1199	0.2709	0.2664	0.04*
C4A	−0.0092 (2)	0.0502 (2)	0.22784 (11)	0.0346 (4)
H4A	−0.0628	0.0505	0.1736	0.042*
C5A	−0.0385 (2)	−0.0800 (2)	0.25262 (11)	0.0328 (4)
H5A	−0.113	−0.1699	0.2152	0.039*
C6A	0.03982 (19)	−0.08112 (19)	0.33190 (10)	0.0284 (4)
H6A	0.0187	−0.1715	0.3483	0.034*
C7A	0.21917 (18)	−0.08886 (17)	0.48812 (10)	0.0238 (3)
C8A	0.11947 (19)	−0.15270 (19)	0.53117 (11)	0.0294 (4)
H8A	0.0551	−0.106	0.5474	0.035*
C9A	0.1137 (2)	−0.28481 (19)	0.55049 (11)	0.0329 (4)
H9A	0.0454	−0.3287	0.5802	0.039*
C10A	0.2069 (2)	−0.35305 (19)	0.52681 (11)	0.0328 (4)
H10A	0.2022	−0.444	0.5399	0.039*
C11A	0.30686 (19)	−0.28940 (19)	0.48412 (11)	0.0320 (4)
H11A	0.3709	−0.3366	0.4679	0.038*
C12A	0.31402 (18)	−0.15642 (18)	0.46491 (10)	0.0274 (4)
H12A	0.3835	−0.1119	0.436	0.033*
C13A	0.35204 (18)	0.18705 (18)	0.60598 (10)	0.0259 (4)
H13A	0.3475	0.0974	0.6209	0.031*
C14A	0.42304 (18)	0.32729 (18)	0.67056 (10)	0.0250 (4)
C15A	0.46818 (19)	0.34694 (19)	0.75658 (11)	0.0309 (4)
H15A	0.4591	0.267	0.7823	0.037*
C16A	0.52983 (18)	0.49809 (19)	0.80343 (11)	0.0309 (4)
H16A	0.5649	0.5303	0.8638	0.037*
C17A	0.5333 (2)	0.5912 (2)	0.75320 (12)	0.0347 (4)
H17A	0.5718	0.6965	0.7738	0.042*
S1B	0.49868 (5)	0.03271 (5)	−0.12555 (3)	0.03013 (12)
N1B	0.96060 (14)	0.28458 (16)	0.04326 (8)	0.0260 (3)
N2B	0.82065 (14)	0.20862 (14)	−0.01346 (8)	0.0233 (3)
C1B	0.96712 (18)	0.36467 (17)	0.12427 (10)	0.0221 (3)
C2B	0.84018 (19)	0.33497 (19)	0.15375 (11)	0.0271 (4)
H2B	0.7471	0.2606	0.1192	0.032*
C3B	0.8508 (2)	0.4147 (2)	0.23387 (11)	0.0320 (4)
H3B	0.764	0.3944	0.2537	0.038*
C4B	0.9854 (2)	0.52359 (19)	0.28560 (11)	0.0331 (4)
H4B	0.9919	0.576	0.3409	0.04*
C5B	1.1098 (2)	0.55446 (19)	0.25521 (11)	0.0331 (4)
H5B	1.2022	0.6302	0.2896	0.04*
C6B	1.10198 (19)	0.47654 (18)	0.17521 (11)	0.0273 (4)
H6B	1.1884	0.4993	0.1551	0.033*
C7B	1.09374 (17)	0.29233 (17)	0.01841 (10)	0.0217 (3)
C8B	1.15424 (18)	0.39775 (19)	−0.02261 (10)	0.0270 (4)
H8B	1.1103	0.4682	−0.0321	0.032*
C9B	1.27897 (19)	0.40038 (19)	−0.04985 (10)	0.0284 (4)
H9B	1.3209	0.4731	−0.0777	0.034*
C10B	1.34251 (18)	0.29745 (19)	−0.03651 (10)	0.0274 (4)
H10B	1.4278	0.2992	−0.0555	0.033*
C11B	1.28180 (19)	0.19156 (19)	0.00450 (11)	0.0292 (4)
H11B	1.3255	0.1209	0.0137	0.035*
C12B	1.15722 (18)	0.18903 (18)	0.03205 (10)	0.0254 (4)
H12B	1.1155	0.1167	0.0602	0.03*
C13B	0.81062 (18)	0.14782 (17)	−0.09080 (10)	0.0235 (3)
H13B	0.8991	0.1555	−0.1075	0.028*
C14B	0.66548 (17)	0.06796 (17)	−0.15229 (10)	0.0226 (3)
C15B	0.63864 (19)	0.01036 (19)	−0.23772 (11)	0.0279 (4)
H15B	0.7159	0.0176	−0.2649	0.033*
C16B	0.48434 (19)	−0.06090 (19)	−0.28138 (11)	0.0304 (4)
H16B	0.447	−0.1064	−0.3409	0.036*
C17B	0.39578 (19)	−0.05744 (19)	−0.22952 (11)	0.0313 (4)
H17B	0.2893	−0.0997	−0.2482	0.038*

	U11	U22	U33	U12	U13	U23
S1A	0.0430 (3)	0.0264 (2)	0.0326 (3)	0.0123 (2)	0.0031 (2)	0.00904 (19)
N1A	0.0417 (9)	0.0208 (7)	0.0206 (7)	0.0096 (6)	0.0033 (7)	0.0038 (6)
N2A	0.0285 (7)	0.0226 (7)	0.0232 (7)	0.0079 (6)	0.0062 (6)	0.0031 (6)
C1A	0.0251 (8)	0.0267 (8)	0.0198 (8)	0.0115 (7)	0.0092 (7)	0.0055 (7)
C2A	0.0304 (9)	0.0260 (9)	0.0263 (9)	0.0095 (7)	0.0091 (8)	0.0068 (7)
C3A	0.0431 (11)	0.0354 (10)	0.0301 (9)	0.0210 (9)	0.0133 (9)	0.0145 (8)
C4A	0.0360 (10)	0.0478 (11)	0.0251 (9)	0.0230 (9)	0.0065 (8)	0.0104 (8)
C5A	0.0287 (9)	0.0366 (10)	0.0274 (9)	0.0113 (8)	0.0042 (8)	0.0009 (8)
C6A	0.0301 (9)	0.0266 (9)	0.0258 (9)	0.0085 (7)	0.0078 (8)	0.0047 (7)
C7A	0.0285 (9)	0.0218 (8)	0.0183 (8)	0.0083 (7)	0.0033 (7)	0.0044 (6)
C8A	0.0260 (9)	0.0316 (9)	0.0295 (9)	0.0102 (7)	0.0087 (8)	0.0057 (8)
C9A	0.0322 (9)	0.0311 (10)	0.0304 (9)	0.0040 (8)	0.0081 (8)	0.0125 (8)
C10A	0.0337 (10)	0.0227 (9)	0.0324 (10)	0.0072 (8)	−0.0050 (8)	0.0074 (8)
C11A	0.0297 (9)	0.0309 (9)	0.0318 (10)	0.0154 (8)	0.0012 (8)	0.0007 (8)
C12A	0.0247 (8)	0.0282 (9)	0.0235 (8)	0.0057 (7)	0.0063 (7)	0.0013 (7)
C13A	0.0291 (9)	0.0240 (8)	0.0249 (9)	0.0101 (7)	0.0074 (7)	0.0071 (7)
C14A	0.0228 (8)	0.0250 (8)	0.0250 (8)	0.0082 (7)	0.0047 (7)	0.0053 (7)
C15A	0.0325 (9)	0.0296 (9)	0.0258 (9)	0.0073 (8)	0.0052 (8)	0.0075 (7)
C16A	0.0252 (9)	0.0345 (10)	0.0238 (9)	0.0065 (8)	0.0032 (7)	−0.0014 (8)
C17A	0.0293 (9)	0.0258 (9)	0.0401 (11)	0.0083 (8)	0.0037 (8)	−0.0017 (8)
S1B	0.0233 (2)	0.0401 (3)	0.0284 (2)	0.01185 (19)	0.00921 (19)	0.0106 (2)
N1B	0.0180 (7)	0.0343 (8)	0.0204 (7)	0.0075 (6)	0.0031 (6)	0.0014 (6)
N2B	0.0205 (7)	0.0243 (7)	0.0221 (7)	0.0069 (6)	0.0031 (6)	0.0050 (6)
C1B	0.0262 (8)	0.0232 (8)	0.0187 (8)	0.0114 (7)	0.0047 (7)	0.0077 (7)
C2B	0.0258 (9)	0.0286 (9)	0.0258 (9)	0.0079 (7)	0.0082 (7)	0.0082 (7)
C3B	0.0393 (10)	0.0343 (10)	0.0314 (9)	0.0176 (8)	0.0194 (9)	0.0129 (8)
C4B	0.0491 (11)	0.0275 (9)	0.0254 (9)	0.0173 (8)	0.0138 (9)	0.0044 (7)
C5B	0.0373 (10)	0.0269 (9)	0.0268 (9)	0.0084 (8)	0.0030 (8)	0.0015 (7)
C6B	0.0268 (9)	0.0284 (9)	0.0253 (9)	0.0097 (7)	0.0061 (7)	0.0063 (7)
C7B	0.0184 (8)	0.0244 (8)	0.0174 (7)	0.0058 (6)	0.0022 (6)	0.0012 (6)
C8B	0.0266 (9)	0.0284 (9)	0.0267 (9)	0.0117 (7)	0.0050 (7)	0.0097 (7)
C9B	0.0290 (9)	0.0293 (9)	0.0242 (9)	0.0064 (7)	0.0078 (7)	0.0094 (7)
C10B	0.0217 (8)	0.0328 (9)	0.0240 (8)	0.0084 (7)	0.0078 (7)	0.0009 (7)
C11B	0.0278 (9)	0.0258 (9)	0.0329 (9)	0.0126 (7)	0.0053 (8)	0.0039 (7)
C12B	0.0262 (9)	0.0218 (8)	0.0248 (8)	0.0062 (7)	0.0056 (7)	0.0056 (7)
C13B	0.0218 (8)	0.0253 (8)	0.0234 (8)	0.0089 (7)	0.0060 (7)	0.0065 (7)
C14B	0.0230 (8)	0.0226 (8)	0.0232 (8)	0.0094 (7)	0.0073 (7)	0.0060 (7)
C15B	0.0250 (9)	0.0321 (9)	0.0254 (9)	0.0111 (7)	0.0073 (7)	0.0044 (7)
C16B	0.0302 (9)	0.0284 (9)	0.0252 (9)	0.0092 (7)	−0.0012 (8)	0.0033 (7)
C17B	0.0217 (8)	0.0317 (9)	0.0356 (10)	0.0072 (7)	0.0004 (8)	0.0113 (8)

S1A—C17A	1.7190 (19)	S1B—C17B	1.7198 (18)
S1A—C14A	1.7247 (17)	S1B—C14B	1.7281 (16)
N1A—N2A	1.3739 (19)	N1B—N2B	1.3751 (18)
N1A—C1A	1.411 (2)	N1B—C1B	1.413 (2)
N1A—C7A	1.433 (2)	N1B—C7B	1.434 (2)
N2A—C13A	1.285 (2)	N2B—C13B	1.288 (2)
C1A—C2A	1.392 (2)	C1B—C2B	1.394 (2)
C1A—C6A	1.394 (2)	C1B—C6B	1.395 (2)
C2A—C3A	1.386 (2)	C2B—C3B	1.386 (2)
C2A—H2A	0.95	C2B—H2B	0.95
C3A—C4A	1.387 (3)	C3B—C4B	1.387 (3)
C3A—H3A	0.95	C3B—H3B	0.95
C4A—C5A	1.378 (3)	C4B—C5B	1.381 (3)
C4A—H4A	0.95	C4B—H4B	0.95
C5A—C6A	1.390 (2)	C5B—C6B	1.386 (2)
C5A—H5A	0.95	C5B—H5B	0.95
C6A—H6A	0.95	C6B—H6B	0.95
C7A—C8A	1.383 (2)	C7B—C8B	1.384 (2)
C7A—C12A	1.387 (2)	C7B—C12B	1.386 (2)
C8A—C9A	1.384 (2)	C8B—C9B	1.385 (2)
C8A—H8A	0.95	C8B—H8B	0.95
C9A—C10A	1.379 (3)	C9B—C10B	1.382 (2)
C9A—H9A	0.95	C9B—H9B	0.95
C10A—C11A	1.379 (3)	C10B—C11B	1.387 (2)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.388 (2)	C11B—C12B	1.387 (2)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—H12A	0.95	C12B—H12B	0.95
C13A—C14A	1.445 (2)	C13B—C14B	1.445 (2)
C13A—H13A	0.95	C13B—H13B	0.95
C14A—C15A	1.367 (2)	C14B—C15B	1.369 (2)
C15A—C16A	1.414 (2)	C15B—C16B	1.413 (2)
C15A—H15A	0.95	C15B—H15B	0.95
C16A—C17A	1.345 (3)	C16B—C17B	1.348 (3)
C16A—H16A	0.95	C16B—H16B	0.95
C17A—H17A	0.95	C17B—H17B	0.95
C17A—S1A—C14A	91.75 (9)	C17B—S1B—C14B	91.65 (8)
N2A—N1A—C1A	116.17 (13)	N2B—N1B—C1B	116.88 (13)
N2A—N1A—C7A	122.29 (13)	N2B—N1B—C7B	121.16 (12)
C1A—N1A—C7A	121.09 (13)	C1B—N1B—C7B	121.74 (13)
C13A—N2A—N1A	119.40 (14)	C13B—N2B—N1B	118.81 (13)
C2A—C1A—C6A	119.30 (15)	C2B—C1B—C6B	119.38 (15)
C2A—C1A—N1A	120.86 (15)	C2B—C1B—N1B	121.00 (15)
C6A—C1A—N1A	119.83 (15)	C6B—C1B—N1B	119.62 (14)
C3A—C2A—C1A	119.70 (16)	C3B—C2B—C1B	119.53 (16)
C3A—C2A—H2A	120.1	C3B—C2B—H2B	120.2
C1A—C2A—H2A	120.1	C1B—C2B—H2B	120.2
C2A—C3A—C4A	121.05 (17)	C2B—C3B—C4B	121.33 (16)
C2A—C3A—H3A	119.5	C2B—C3B—H3B	119.3
C4A—C3A—H3A	119.5	C4B—C3B—H3B	119.3
C5A—C4A—C3A	119.19 (16)	C5B—C4B—C3B	118.76 (16)
C5A—C4A—H4A	120.4	C5B—C4B—H4B	120.6
C3A—C4A—H4A	120.4	C3B—C4B—H4B	120.6
C4A—C5A—C6A	120.59 (17)	C4B—C5B—C6B	120.98 (17)
C4A—C5A—H5A	119.7	C4B—C5B—H5B	119.5
C6A—C5A—H5A	119.7	C6B—C5B—H5B	119.5
C5A—C6A—C1A	120.16 (16)	C5B—C6B—C1B	119.99 (16)
C5A—C6A—H6A	119.9	C5B—C6B—H6B	120
C1A—C6A—H6A	119.9	C1B—C6B—H6B	120
C8A—C7A—C12A	120.14 (15)	C8B—C7B—C12B	120.21 (15)
C8A—C7A—N1A	120.52 (15)	C8B—C7B—N1B	120.15 (14)
C12A—C7A—N1A	119.34 (14)	C12B—C7B—N1B	119.57 (14)
C7A—C8A—C9A	119.80 (16)	C7B—C8B—C9B	119.86 (15)
C7A—C8A—H8A	120.1	C7B—C8B—H8B	120.1
C9A—C8A—H8A	120.1	C9B—C8B—H8B	120.1
C10A—C9A—C8A	120.23 (16)	C10B—C9B—C8B	120.13 (15)
C10A—C9A—H9A	119.9	C10B—C9B—H9B	119.9
C8A—C9A—H9A	119.9	C8B—C9B—H9B	119.9
C11A—C10A—C9A	120.12 (16)	C9B—C10B—C11B	120.04 (15)
C11A—C10A—H10A	119.9	C9B—C10B—H10B	120
C9A—C10A—H10A	119.9	C11B—C10B—H10B	120
C10A—C11A—C12A	120.06 (16)	C12B—C11B—C10B	119.91 (16)
C10A—C11A—H11A	120	C12B—C11B—H11B	120
C12A—C11A—H11A	120	C10B—C11B—H11B	120
C7A—C12A—C11A	119.65 (15)	C7B—C12B—C11B	119.83 (15)
C7A—C12A—H12A	120.2	C7B—C12B—H12B	120.1
C11A—C12A—H12A	120.2	C11B—C12B—H12B	120.1
N2A—C13A—C14A	120.29 (15)	N2B—C13B—C14B	120.34 (15)
N2A—C13A—H13A	119.9	N2B—C13B—H13B	119.8
C14A—C13A—H13A	119.9	C14B—C13B—H13B	119.8
C15A—C14A—C13A	126.66 (16)	C15B—C14B—C13B	126.43 (15)
C15A—C14A—S1A	110.41 (13)	C15B—C14B—S1B	110.52 (12)
C13A—C14A—S1A	122.92 (13)	C13B—C14B—S1B	123.05 (12)
C14A—C15A—C16A	113.27 (16)	C14B—C15B—C16B	113.16 (15)
C14A—C15A—H15A	123.4	C14B—C15B—H15B	123.4
C16A—C15A—H15A	123.4	C16B—C15B—H15B	123.4
C17A—C16A—C15A	112.64 (16)	C17B—C16B—C15B	112.77 (16)
C17A—C16A—H16A	123.7	C17B—C16B—H16B	123.6
C15A—C16A—H16A	123.7	C15B—C16B—H16B	123.6
C16A—C17A—S1A	111.92 (13)	C16B—C17B—S1B	111.90 (13)
C16A—C17A—H17A	124	C16B—C17B—H17B	124.1
S1A—C17A—H17A	124	S1B—C17B—H17B	124.1
C1A—N1A—N2A—C13A	171.50 (14)	C1B—N1B—N2B—C13B	172.48 (14)
C7A—N1A—N2A—C13A	−0.8 (2)	C7B—N1B—N2B—C13B	−2.2 (2)
N2A—N1A—C1A—C2A	19.8 (2)	N2B—N1B—C1B—C2B	17.7 (2)
C7A—N1A—C1A—C2A	−167.71 (15)	C7B—N1B—C1B—C2B	−167.66 (14)
N2A—N1A—C1A—C6A	−159.52 (14)	N2B—N1B—C1B—C6B	−161.46 (14)
C7A—N1A—C1A—C6A	12.9 (2)	C7B—N1B—C1B—C6B	13.2 (2)
C6A—C1A—C2A—C3A	0.2 (2)	C6B—C1B—C2B—C3B	−1.4 (2)
N1A—C1A—C2A—C3A	−179.22 (15)	N1B—C1B—C2B—C3B	179.43 (15)
C1A—C2A—C3A—C4A	−0.2 (3)	C1B—C2B—C3B—C4B	−0.1 (3)
C2A—C3A—C4A—C5A	0.2 (3)	C2B—C3B—C4B—C5B	1.5 (3)
C3A—C4A—C5A—C6A	−0.1 (3)	C3B—C4B—C5B—C6B	−1.3 (3)
C4A—C5A—C6A—C1A	0.0 (3)	C4B—C5B—C6B—C1B	−0.3 (3)
C2A—C1A—C6A—C5A	0.0 (2)	C2B—C1B—C6B—C5B	1.6 (2)
N1A—C1A—C6A—C5A	179.33 (15)	N1B—C1B—C6B—C5B	−179.22 (15)
N2A—N1A—C7A—C8A	75.1 (2)	N2B—N1B—C7B—C8B	83.36 (19)
C1A—N1A—C7A—C8A	−96.82 (19)	C1B—N1B—C7B—C8B	−91.07 (19)
N2A—N1A—C7A—C12A	−103.95 (18)	N2B—N1B—C7B—C12B	−93.54 (18)
C1A—N1A—C7A—C12A	84.1 (2)	C1B—N1B—C7B—C12B	92.03 (19)
C12A—C7A—C8A—C9A	−0.5 (2)	C12B—C7B—C8B—C9B	−0.2 (2)
N1A—C7A—C8A—C9A	−179.57 (15)	N1B—C7B—C8B—C9B	−177.12 (14)
C7A—C8A—C9A—C10A	−0.1 (3)	C7B—C8B—C9B—C10B	0.3 (2)
C8A—C9A—C10A—C11A	0.4 (3)	C8B—C9B—C10B—C11B	−0.3 (3)
C9A—C10A—C11A—C12A	0.0 (3)	C9B—C10B—C11B—C12B	0.0 (3)
C8A—C7A—C12A—C11A	0.9 (2)	C8B—C7B—C12B—C11B	0.0 (2)
N1A—C7A—C12A—C11A	179.96 (15)	N1B—C7B—C12B—C11B	176.93 (14)
C10A—C11A—C12A—C7A	−0.6 (2)	C10B—C11B—C12B—C7B	0.1 (2)
N1A—N2A—C13A—C14A	−179.61 (14)	N1B—N2B—C13B—C14B	−179.59 (13)
N2A—C13A—C14A—C15A	169.63 (17)	N2B—C13B—C14B—C15B	173.46 (16)
N2A—C13A—C14A—S1A	−9.3 (2)	N2B—C13B—C14B—S1B	−6.5 (2)
C17A—S1A—C14A—C15A	−0.57 (14)	C17B—S1B—C14B—C15B	−0.43 (13)
C17A—S1A—C14A—C13A	178.54 (15)	C17B—S1B—C14B—C13B	179.51 (14)
C13A—C14A—C15A—C16A	−178.07 (16)	C13B—C14B—C15B—C16B	−179.54 (15)
S1A—C14A—C15A—C16A	1.0 (2)	S1B—C14B—C15B—C16B	0.40 (19)
C14A—C15A—C16A—C17A	−1.0 (2)	C14B—C15B—C16B—C17B	−0.1 (2)
C15A—C16A—C17A—S1A	0.6 (2)	C15B—C16B—C17B—S1B	−0.2 (2)
C14A—S1A—C17A—C16A	0.00 (14)	C14B—S1B—C17B—C16B	0.35 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···Cg5i	0.95	2.76	3.553 (2)	141
C8A—H8A···Cg2ii	0.95	2.97	3.740 (2)	139
C15B—H15B···Cg2iii	0.95	2.60	3.484 (2)	156
C16A—H16A···Cg6iv	0.95	2.72	3.5725 (19)	150
C16B—H16B···Cg3v	0.95	2.80	3.659 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1A–C6A, C7A–C12A, C1B–C6B and C7B–C12B phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3A—H3A⋯Cg5i	0.95	2.76	3.553 (2)	141
C8A—H8A⋯Cg2ii	0.95	2.97	3.740 (2)	139
C15B—H15B⋯Cg2iii	0.95	2.60	3.484 (2)	156
C16A—H16A⋯Cg6iv	0.95	2.72	3.5725 (19)	150
C16B—H16B⋯Cg3v	0.95	2.80	3.659 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .