1-{(E)-[4-(4-Meth-oxy-phen-yl)butan-2-yl-idene]amino}-3-methyl-thio-urea.

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(13)H(19)N(3)OS, which differ in the conformations of the residues linking the thio-urea and the terminal benzene ring, as manifested in the C(m)-C(m)-C(a)-C(a) torsion angles [78.03 (16) and -93.64 (16)°, respectively; m = methyl-ene and a = aromatic]. The dihedral angles [84.40 (4) and 88.28 (5)°] formed between the thio-urea residue and the benzene ring indicate an almost orthogonal relationship. In each thio-urea residue, the N-H hydrogen atoms are anti, and the terminal N-H hydrogen atom forms an intra-molecular N-H⋯N hydrogen bond with the imine-N atom. In each case, the conformation about the imine C=N double bond [1.2812 (17) and 1.2801 (17) Å] is E. In the crystal, the mol-ecules are connected by N-H⋯S hydrogen bonds and these are connected into four mol-ecule aggregates via N-H⋯O hydrogen bonds, which are assembled into a two-dimensional array parallel to (011) via C-H⋯π and π-π inter-actions [ring centroid-centroid distance = 3.8344 (9) Å].

Related literature

For background to chalcone thio­semicarbazides, see: Zhang et al. (2011 ▶). For background to hydrazinecarbodithio­ates, see: Khoo et al. (2005 ▶); Chan et al. (2008 ▶); Ravoof et al. (2010 ▶). For related syntheses, see: Tian et al. (1997 ▶); Tarafder et al. (2002 ▶).

Experimental

Crystal data

C13H19N3OS

M = 265.37

Triclinic,

a = 9.6344 (4) Å

b = 11.1759 (6) Å

c = 13.4619 (8) Å

α = 80.324 (5)°

β = 87.103 (4)°

γ = 76.360 (4)°

V = 1388.48 (13) Å3

Z = 4

Cu Kα radiation

μ = 2.01 mm−1

T = 100 K

0.41 × 0.23 × 0.14 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.51, T max = 0.75

18287 measured reflections

5312 independent reflections

4995 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.01

5312 reflections

343 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.41 e Å−3

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: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201611X/qm2063sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201611X/qm2063Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201611X/qm2063Isup3.cml

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

C13H19N3OS	Z = 4
Mr = 265.37	F(000) = 568
Triclinic, P1	Dx = 1.269 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 9.6344 (4) Å	Cell parameters from 10673 reflections
b = 11.1759 (6) Å	θ = 3–71°
c = 13.4619 (8) Å	µ = 2.01 mm−1
α = 80.324 (5)°	T = 100 K
β = 87.103 (4)°	Prism, colourless
γ = 76.360 (4)°	0.41 × 0.23 × 0.14 mm
V = 1388.48 (13) Å3

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5312 independent reflections
Radiation source: sealed X-ray tube	4995 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.1952 pixels mm-1	θmax = 71.6°, θmin = 3.3°
ω/2θ scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→13
Tmin = 0.51, Tmax = 0.75	l = −16→16
18287 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.065P)2 + 0.5168P] where P = (Fo2 + 2Fc2)/3
5312 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.29 e Å−3
4 restraints	Δρmin = −0.41 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.20415 (3)	0.32321 (3)	0.48243 (2)	0.01907 (11)
O1	1.27782 (10)	−0.24724 (9)	0.93804 (7)	0.0204 (2)
N1	0.34458 (12)	0.15989 (11)	0.63195 (9)	0.0183 (2)
H1N	0.4267 (12)	0.1245 (15)	0.6602 (12)	0.022*
N2	0.47979 (11)	0.26896 (10)	0.52508 (8)	0.0144 (2)
H2N	0.4854 (17)	0.3310 (12)	0.4776 (10)	0.017*
N3	0.59623 (11)	0.19555 (10)	0.57947 (8)	0.0145 (2)
C1	0.21511 (15)	0.11973 (14)	0.66758 (12)	0.0241 (3)
H1A	0.1413	0.1919	0.6817	0.036*
H1B	0.2356	0.0584	0.7293	0.036*
H1C	0.1813	0.0818	0.6157	0.036*
C2	0.34971 (14)	0.24605 (12)	0.55167 (10)	0.0147 (3)
C3	0.71806 (14)	0.22229 (12)	0.56058 (10)	0.0147 (3)
C4	0.74688 (14)	0.32895 (13)	0.48538 (10)	0.0182 (3)
H4A	0.7270	0.3172	0.4174	0.027*
H4B	0.8472	0.3322	0.4892	0.027*
H4C	0.6853	0.4072	0.5003	0.027*
C5	0.84347 (14)	0.13959 (13)	0.61947 (10)	0.0170 (3)
H5A	0.8808	0.1903	0.6607	0.020*
H5B	0.9199	0.1102	0.5713	0.020*
C6	0.81204 (14)	0.02645 (13)	0.68873 (11)	0.0206 (3)
H6A	0.7314	0.0545	0.7343	0.025*
H6B	0.7824	−0.0286	0.6476	0.025*
C7	0.93936 (14)	−0.04719 (13)	0.75113 (10)	0.0174 (3)
C8	0.97580 (14)	−0.00550 (13)	0.83614 (10)	0.0174 (3)
H8	0.9211	0.0709	0.8534	0.021*
C9	1.08986 (14)	−0.07296 (13)	0.89598 (10)	0.0165 (3)
H9	1.1128	−0.0427	0.9535	0.020*
C10	1.17070 (14)	−0.18502 (13)	0.87166 (10)	0.0164 (3)
C11	1.13875 (15)	−0.22751 (13)	0.78626 (11)	0.0206 (3)
H11	1.1945	−0.3033	0.7685	0.025*
C12	1.02383 (16)	−0.15758 (13)	0.72690 (11)	0.0209 (3)
H12	1.0028	−0.1864	0.6682	0.025*
C13	1.35572 (17)	−0.36669 (14)	0.91966 (12)	0.0280 (3)
H13A	1.2909	−0.4232	0.9244	0.042*
H13B	1.4311	−0.4003	0.9699	0.042*
H13C	1.3988	−0.3588	0.8521	0.042*
S2	0.50040 (3)	0.51322 (3)	0.32073 (2)	0.01570 (10)
O2	−0.50895 (10)	0.90797 (9)	−0.24093 (7)	0.0197 (2)
N4	0.35843 (12)	0.67030 (11)	0.16874 (9)	0.0175 (2)
H4N	0.2787 (13)	0.6966 (15)	0.1361 (12)	0.021*
N5	0.22689 (12)	0.55527 (10)	0.27342 (8)	0.0151 (2)
H5N	0.2193 (17)	0.4984 (13)	0.3255 (9)	0.018*
N6	0.11708 (12)	0.60815 (10)	0.20570 (8)	0.0156 (2)
C14	0.48459 (14)	0.71634 (14)	0.13471 (11)	0.0214 (3)
H14A	0.5147	0.7551	0.1875	0.032*
H14B	0.4623	0.7782	0.0735	0.032*
H14C	0.5618	0.6467	0.1202	0.032*
C15	0.35546 (14)	0.58411 (12)	0.24972 (10)	0.0140 (3)
C16	−0.00410 (14)	0.58042 (12)	0.22484 (10)	0.0152 (3)
C17	−0.04030 (15)	0.49618 (14)	0.31617 (11)	0.0209 (3)
H17A	0.0148	0.4107	0.3147	0.031*
H17B	−0.1426	0.4982	0.3166	0.031*
H17C	−0.0168	0.5244	0.3770	0.031*
C18	−0.11934 (14)	0.63481 (13)	0.14771 (10)	0.0181 (3)
H18A	−0.1999	0.6888	0.1793	0.022*
H18B	−0.1550	0.5657	0.1287	0.022*
C19	−0.07400 (15)	0.71084 (14)	0.05199 (11)	0.0225 (3)
H19A	−0.0429	0.7827	0.0700	0.027*
H19B	0.0088	0.6584	0.0212	0.027*
C20	−0.19197 (14)	0.75844 (13)	−0.02456 (10)	0.0189 (3)
C21	−0.20533 (16)	0.69260 (14)	−0.10058 (12)	0.0241 (3)
H21	−0.1412	0.6142	−0.1027	0.029*
C22	−0.31004 (16)	0.73782 (13)	−0.17421 (11)	0.0229 (3)
H22	−0.3162	0.6911	−0.2260	0.027*
C23	−0.40494 (14)	0.85161 (12)	−0.17094 (10)	0.0161 (3)
C24	−0.39597 (14)	0.91792 (13)	−0.09373 (10)	0.0166 (3)
H24	−0.4620	0.9952	−0.0905	0.020*
C25	−0.29074 (14)	0.87139 (13)	−0.02154 (10)	0.0183 (3)
H25	−0.2858	0.9173	0.0310	0.022*
C26	−0.50890 (16)	0.84812 (14)	−0.32718 (11)	0.0236 (3)
H26A	−0.4153	0.8393	−0.3609	0.035*
H26B	−0.5828	0.8987	−0.3740	0.035*
H26C	−0.5286	0.7655	−0.3056	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.01121 (17)	0.02285 (19)	0.01953 (19)	−0.00212 (13)	−0.00427 (12)	0.00540 (14)
O1	0.0189 (5)	0.0203 (5)	0.0185 (5)	0.0022 (4)	−0.0064 (4)	−0.0012 (4)
N1	0.0115 (5)	0.0217 (6)	0.0190 (6)	−0.0038 (4)	−0.0029 (4)	0.0054 (5)
N2	0.0122 (5)	0.0158 (6)	0.0133 (5)	−0.0030 (4)	−0.0032 (4)	0.0036 (4)
N3	0.0124 (5)	0.0160 (5)	0.0134 (5)	−0.0012 (4)	−0.0033 (4)	0.0007 (4)
C1	0.0135 (6)	0.0271 (8)	0.0276 (8)	−0.0058 (6)	−0.0012 (6)	0.0089 (6)
C2	0.0122 (6)	0.0166 (6)	0.0147 (6)	−0.0021 (5)	−0.0018 (5)	−0.0020 (5)
C3	0.0131 (6)	0.0177 (6)	0.0130 (6)	−0.0036 (5)	−0.0012 (5)	−0.0010 (5)
C4	0.0138 (6)	0.0226 (7)	0.0164 (6)	−0.0055 (5)	−0.0020 (5)	0.0046 (5)
C5	0.0120 (6)	0.0200 (7)	0.0171 (6)	−0.0038 (5)	−0.0024 (5)	0.0032 (5)
C6	0.0152 (6)	0.0220 (7)	0.0224 (7)	−0.0057 (5)	−0.0056 (5)	0.0060 (6)
C7	0.0139 (6)	0.0188 (7)	0.0176 (6)	−0.0059 (5)	−0.0019 (5)	0.0056 (5)
C8	0.0151 (6)	0.0160 (6)	0.0187 (7)	−0.0024 (5)	0.0014 (5)	0.0019 (5)
C9	0.0165 (6)	0.0192 (7)	0.0136 (6)	−0.0055 (5)	−0.0002 (5)	0.0001 (5)
C10	0.0134 (6)	0.0197 (7)	0.0142 (6)	−0.0039 (5)	−0.0014 (5)	0.0031 (5)
C11	0.0221 (7)	0.0181 (7)	0.0192 (7)	−0.0007 (5)	−0.0024 (5)	−0.0017 (5)
C12	0.0253 (7)	0.0209 (7)	0.0166 (7)	−0.0060 (6)	−0.0059 (6)	−0.0003 (5)
C13	0.0268 (8)	0.0250 (8)	0.0263 (8)	0.0076 (6)	−0.0089 (6)	−0.0044 (6)
S2	0.01168 (16)	0.01806 (18)	0.01548 (17)	−0.00205 (12)	−0.00432 (12)	0.00184 (13)
O2	0.0198 (5)	0.0215 (5)	0.0161 (5)	0.0002 (4)	−0.0070 (4)	−0.0032 (4)
N4	0.0121 (5)	0.0198 (6)	0.0181 (6)	−0.0039 (4)	−0.0049 (4)	0.0057 (5)
N5	0.0121 (5)	0.0171 (6)	0.0139 (5)	−0.0029 (4)	−0.0038 (4)	0.0042 (4)
N6	0.0132 (5)	0.0169 (6)	0.0149 (5)	−0.0021 (4)	−0.0042 (4)	0.0014 (4)
C14	0.0158 (6)	0.0245 (7)	0.0231 (7)	−0.0090 (6)	−0.0034 (5)	0.0058 (6)
C15	0.0132 (6)	0.0136 (6)	0.0150 (6)	−0.0018 (5)	−0.0016 (5)	−0.0032 (5)
C16	0.0134 (6)	0.0162 (6)	0.0151 (6)	−0.0026 (5)	−0.0014 (5)	−0.0005 (5)
C17	0.0150 (6)	0.0270 (8)	0.0191 (7)	−0.0076 (6)	−0.0027 (5)	0.0051 (6)
C18	0.0138 (6)	0.0224 (7)	0.0176 (7)	−0.0067 (5)	−0.0030 (5)	0.0030 (5)
C19	0.0152 (6)	0.0299 (8)	0.0199 (7)	−0.0077 (6)	−0.0044 (5)	0.0077 (6)
C20	0.0147 (6)	0.0236 (7)	0.0165 (7)	−0.0073 (5)	−0.0010 (5)	0.0061 (5)
C21	0.0217 (7)	0.0197 (7)	0.0258 (7)	0.0027 (6)	−0.0046 (6)	0.0015 (6)
C22	0.0256 (7)	0.0211 (7)	0.0211 (7)	−0.0012 (6)	−0.0049 (6)	−0.0054 (6)
C23	0.0146 (6)	0.0181 (7)	0.0143 (6)	−0.0050 (5)	−0.0026 (5)	0.0031 (5)
C24	0.0153 (6)	0.0172 (7)	0.0157 (6)	−0.0027 (5)	0.0002 (5)	0.0005 (5)
C25	0.0186 (6)	0.0248 (7)	0.0129 (6)	−0.0095 (5)	−0.0007 (5)	−0.0009 (5)
C26	0.0269 (7)	0.0262 (8)	0.0181 (7)	−0.0043 (6)	−0.0084 (6)	−0.0045 (6)

S1—C2	1.6943 (13)	S2—C15	1.6881 (13)
O1—C10	1.3759 (16)	O2—C23	1.3736 (16)
O1—C13	1.4236 (17)	O2—C26	1.4341 (16)
N1—C2	1.3284 (18)	N4—C15	1.3319 (18)
N1—C1	1.4556 (17)	N4—C14	1.4530 (17)
N1—H1N	0.871 (9)	N4—H4n	0.869 (9)
N2—C2	1.3563 (17)	N5—C15	1.3616 (17)
N2—N3	1.3837 (15)	N5—N6	1.3860 (15)
N2—H2N	0.870 (9)	N5—H5n	0.875 (9)
N3—C3	1.2812 (17)	N6—C16	1.2801 (17)
C1—H1A	0.9800	C14—H14A	0.9800
C1—H1B	0.9800	C14—H14B	0.9800
C1—H1C	0.9800	C14—H14C	0.9800
C3—C4	1.4983 (18)	C16—C17	1.4974 (19)
C3—C5	1.5054 (17)	C16—C18	1.5055 (17)
C4—H4A	0.9800	C17—H17A	0.9800
C4—H4B	0.9800	C17—H17B	0.9800
C4—H4C	0.9800	C17—H17C	0.9800
C5—C6	1.5217 (19)	C18—C19	1.5242 (19)
C5—H5A	0.9900	C18—H18A	0.9900
C5—H5B	0.9900	C18—H18B	0.9900
C6—C7	1.5110 (18)	C19—C20	1.5119 (18)
C6—H6A	0.9900	C19—H19A	0.9900
C6—H6B	0.9900	C19—H19B	0.9900
C7—C12	1.388 (2)	C20—C21	1.384 (2)
C7—C8	1.395 (2)	C20—C25	1.396 (2)
C8—C9	1.3855 (19)	C21—C22	1.396 (2)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.3908 (19)	C22—C23	1.3863 (19)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.3893 (19)	C23—C24	1.3911 (19)
C11—C12	1.3952 (19)	C24—C25	1.3870 (19)
C11—H11	0.9500	C24—H24	0.9500
C12—H12	0.9500	C25—H25	0.9500
C13—H13A	0.9800	C26—H26A	0.9800
C13—H13B	0.9800	C26—H26B	0.9800
C13—H13C	0.9800	C26—H26C	0.9800
C10—O1—C13	116.80 (11)	C23—O2—C26	116.28 (10)
C2—N1—C1	123.67 (11)	C15—N4—C14	123.68 (11)
C2—N1—H1N	114.8 (11)	C15—N4—H4N	114.8 (11)
C1—N1—H1N	121.4 (11)	C14—N4—H4N	121.5 (11)
C2—N2—N3	117.48 (11)	C15—N5—N6	117.04 (11)
C2—N2—H2N	119.0 (11)	C15—N5—H5N	119.8 (11)
N3—N2—H2N	123.5 (11)	N6—N5—H5N	122.7 (11)
C3—N3—N2	118.22 (11)	C16—N6—N5	118.43 (11)
N1—C1—H1A	109.5	N4—C14—H14A	109.5
N1—C1—H1B	109.5	N4—C14—H14B	109.5
H1A—C1—H1B	109.5	H14A—C14—H14B	109.5
N1—C1—H1C	109.5	N4—C14—H14C	109.5
H1A—C1—H1C	109.5	H14A—C14—H14C	109.5
H1B—C1—H1C	109.5	H14B—C14—H14C	109.5
N1—C2—N2	116.68 (11)	N4—C15—N5	116.10 (11)
N1—C2—S1	123.03 (10)	N4—C15—S2	123.13 (10)
N2—C2—S1	120.28 (10)	N5—C15—S2	120.77 (10)
N3—C3—C4	125.83 (12)	N6—C16—C17	125.70 (12)
N3—C3—C5	117.16 (11)	N6—C16—C18	117.21 (11)
C4—C3—C5	117.01 (11)	C17—C16—C18	117.07 (11)
C3—C4—H4A	109.5	C16—C17—H17A	109.5
C3—C4—H4B	109.5	C16—C17—H17B	109.5
H4A—C4—H4B	109.5	H17A—C17—H17B	109.5
C3—C4—H4C	109.5	C16—C17—H17C	109.5
H4A—C4—H4C	109.5	H17A—C17—H17C	109.5
H4B—C4—H4C	109.5	H17B—C17—H17C	109.5
C3—C5—C6	115.30 (11)	C16—C18—C19	115.25 (11)
C3—C5—H5A	108.4	C16—C18—H18A	108.5
C6—C5—H5A	108.4	C19—C18—H18A	108.5
C3—C5—H5B	108.4	C16—C18—H18B	108.5
C6—C5—H5B	108.4	C19—C18—H18B	108.5
H5A—C5—H5B	107.5	H18A—C18—H18B	107.5
C7—C6—C5	112.58 (11)	C20—C19—C18	112.97 (11)
C7—C6—H6A	109.1	C20—C19—H19A	109.0
C5—C6—H6A	109.1	C18—C19—H19A	109.0
C7—C6—H6B	109.1	C20—C19—H19B	109.0
C5—C6—H6B	109.1	C18—C19—H19B	109.0
H6A—C6—H6B	107.8	H19A—C19—H19B	107.8
C12—C7—C8	117.58 (12)	C21—C20—C25	117.58 (12)
C12—C7—C6	121.97 (12)	C21—C20—C19	121.45 (13)
C8—C7—C6	120.45 (12)	C25—C20—C19	120.97 (13)
C9—C8—C7	121.52 (12)	C20—C21—C22	122.09 (13)
C9—C8—H8	119.2	C20—C21—H21	119.0
C7—C8—H8	119.2	C22—C21—H21	119.0
C8—C9—C10	119.84 (12)	C23—C22—C21	119.25 (13)
C8—C9—H9	120.1	C23—C22—H22	120.4
C10—C9—H9	120.1	C21—C22—H22	120.4
O1—C10—C11	124.80 (12)	O2—C23—C22	124.70 (12)
O1—C10—C9	115.30 (12)	O2—C23—C24	115.59 (12)
C11—C10—C9	119.89 (12)	C22—C23—C24	119.69 (12)
C10—C11—C12	119.18 (13)	C25—C24—C23	120.07 (12)
C10—C11—H11	120.4	C25—C24—H24	120.0
C12—C11—H11	120.4	C23—C24—H24	120.0
C7—C12—C11	121.94 (13)	C24—C25—C20	121.28 (13)
C7—C12—H12	119.0	C24—C25—H25	119.4
C11—C12—H12	119.0	C20—C25—H25	119.4
O1—C13—H13A	109.5	O2—C26—H26A	109.5
O1—C13—H13B	109.5	O2—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
O1—C13—H13C	109.5	O2—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C2—N2—N3—C3	−174.61 (11)	C15—N5—N6—C16	178.41 (11)
C1—N1—C2—N2	−176.85 (13)	C14—N4—C15—N5	177.38 (12)
C1—N1—C2—S1	1.81 (19)	C14—N4—C15—S2	−2.45 (19)
N3—N2—C2—N1	4.06 (17)	N6—N5—C15—N4	6.56 (17)
N3—N2—C2—S1	−174.64 (9)	N6—N5—C15—S2	−173.61 (9)
N2—N3—C3—C4	1.38 (19)	N5—N6—C16—C17	1.1 (2)
N2—N3—C3—C5	−178.93 (10)	N5—N6—C16—C18	−177.38 (11)
N3—C3—C5—C6	5.04 (18)	N6—C16—C18—C19	3.64 (18)
C4—C3—C5—C6	−175.24 (12)	C17—C16—C18—C19	−174.98 (12)
C3—C5—C6—C7	−175.80 (11)	C16—C18—C19—C20	177.51 (12)
C5—C6—C7—C12	−102.04 (15)	C18—C19—C20—C21	−93.64 (16)
C5—C6—C7—C8	78.03 (16)	C18—C19—C20—C25	87.00 (16)
C12—C7—C8—C9	−1.6 (2)	C25—C20—C21—C22	2.1 (2)
C6—C7—C8—C9	178.36 (12)	C19—C20—C21—C22	−177.31 (13)
C7—C8—C9—C10	−0.1 (2)	C20—C21—C22—C23	−0.7 (2)
C13—O1—C10—C11	−3.41 (19)	C26—O2—C23—C22	−5.62 (19)
C13—O1—C10—C9	175.41 (12)	C26—O2—C23—C24	172.95 (12)
C8—C9—C10—O1	−177.48 (11)	C21—C22—C23—O2	177.50 (13)
C8—C9—C10—C11	1.4 (2)	C21—C22—C23—C24	−1.0 (2)
O1—C10—C11—C12	177.71 (12)	O2—C23—C24—C25	−177.41 (11)
C9—C10—C11—C12	−1.1 (2)	C22—C23—C24—C25	1.2 (2)
C8—C7—C12—C11	1.9 (2)	C23—C24—C25—C20	0.2 (2)
C6—C7—C12—C11	−178.01 (13)	C21—C20—C25—C24	−1.8 (2)
C10—C11—C12—C7	−0.6 (2)	C19—C20—C25—C24	177.55 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3	0.87 (1)	2.15 (1)	2.5931 (16)	111 (1)
N4—H4n···N6	0.87 (1)	2.13 (1)	2.5818 (17)	112 (1)
N2—H2n···S2	0.87 (1)	2.70 (1)	3.5686 (11)	176 (1)
N5—H5n···S1	0.88 (1)	2.65 (1)	3.5276 (11)	178 (1)
N1—H1n···O2i	0.87 (1)	2.51 (2)	3.0979 (16)	125 (1)
C1—H1B···Cg1ii	0.98	2.94	3.5930 (17)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3	0.87 (1)	2.15 (1)	2.5931 (16)	111 (1)
N4—H4n⋯N6	0.87 (1)	2.13 (1)	2.5818 (17)	112 (1)
N2—H2n⋯S2	0.87 (1)	2.70 (1)	3.5686 (11)	176 (1)
N5—H5n⋯S1	0.88 (1)	2.65 (1)	3.5276 (11)	178 (1)
N1—H1n⋯O2i	0.87 (1)	2.51 (2)	3.0979 (16)	125 (1)
C1—H1B⋯Cg1ii	0.98	2.94	3.5930 (17)	125

Symmetry codes: (i) ; (ii) .