4-[(E)-4-Methoxy-benzyl-ideneamino]-3-{1-[4-(2-methyl-prop-yl)phen-yl]eth-yl}-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(22)H(26)N(4)OS, the benzene rings of the (2-methyl-prop-yl)phenyl and 4-methoxy-phenyl units form dihedral angles of 66.85 (3) and 25.96 (3)°, respectively, with the triazole ring. The dihedral angle between the two benzene rings is 87.42 (2)°. The -CH(CH(3)) linkage is disordered over two orientations with occupancies of 0.907 (3) and 0.093 (3). An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif. Inter-molecular N-H⋯S hydrogen bonds and C-H⋯π inter-actions are observed.

Related literature

For the pharmaceutical applications of triazole compounds, see: Amir & Kumar (2007 ▶); Clemons et al. (2004 ▶); Demirbas & Ugurluoglu (2004 ▶); Demirbas et al. (2002 ▶); Johnston (2002 ▶); Shujuan et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H26N4OS

M = 394.53

Triclinic,

a = 7.9446 (1) Å

b = 11.1392 (2) Å

c = 12.3797 (2) Å

α = 77.769 (1)°

β = 79.025 (1)°

γ = 80.063 (1)°

V = 1041.08 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.50 × 0.27 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.918, T max = 0.977

38166 measured reflections

9105 independent reflections

7573 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.03

9105 reflections

281 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014949/ci2785sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014949/ci2785Isup2.hkl

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

C22H26N4OS	Z = 2
Mr = 394.53	F(000) = 420
Triclinic, P1	Dx = 1.259 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9446 (1) Å	Cell parameters from 9938 reflections
b = 11.1392 (2) Å	θ = 2.8–36.8°
c = 12.3797 (2) Å	µ = 0.18 mm−1
α = 77.769 (1)°	T = 100 K
β = 79.025 (1)°	Block, colourless
γ = 80.063 (1)°	0.50 × 0.27 × 0.13 mm
V = 1041.08 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	9105 independent reflections
Radiation source: fine-focus sealed tube	7573 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 35.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.918, Tmax = 0.977	k = −17→17
38166 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.2526P] where P = (Fo2 + 2Fc2)/3
9105 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
S1	0.28546 (3)	0.91565 (2)	0.481988 (17)	0.01833 (5)
O1	1.15746 (9)	0.44217 (7)	0.65279 (6)	0.02374 (14)
N1	0.01719 (10)	0.92699 (7)	0.65460 (6)	0.01744 (13)
N2	−0.04031 (10)	0.86893 (8)	0.76193 (6)	0.01929 (14)
N3	0.23009 (9)	0.79552 (7)	0.70327 (6)	0.01442 (12)
N4	0.38158 (9)	0.71119 (7)	0.70940 (6)	0.01542 (12)
C1	0.17881 (10)	0.88191 (8)	0.61363 (7)	0.01473 (13)
C2	0.09098 (11)	0.78783 (8)	0.78932 (7)	0.01672 (14)
C3	0.09472 (18)	0.69214 (14)	0.89541 (11)	0.0151 (2)	0.907 (3)
H3A	0.1528	0.6133	0.8746	0.018*	0.907 (3)
C14	−0.09117 (14)	0.67381 (11)	0.95160 (9)	0.0238 (3)	0.907 (3)
H14A	−0.1459	0.6413	0.9034	0.036*	0.907 (3)
H14B	−0.1551	0.7520	0.9651	0.036*	0.907 (3)
H14C	−0.0886	0.6167	1.0214	0.036*	0.907 (3)
C3A	0.061 (2)	0.7326 (14)	0.9050 (13)	0.021 (2)	0.093 (3)
H3AA	−0.0491	0.7717	0.9410	0.025*	0.093 (3)
C14A	0.0488 (19)	0.6028 (14)	0.9039 (10)	0.037 (4)	0.093 (3)
H14D	−0.0359	0.6001	0.8588	0.056*	0.093 (3)
H14E	0.0149	0.5605	0.9790	0.056*	0.093 (3)
H14F	0.1593	0.5630	0.8731	0.056*	0.093 (3)
C13	0.73078 (13)	0.89352 (10)	1.25067 (9)	0.02513 (18)
H13A	0.8040	0.9571	1.2222	0.038*
H13B	0.8007	0.8137	1.2582	0.038*
H13C	0.6668	0.9055	1.3225	0.038*
C4	0.19848 (11)	0.72643 (8)	0.97397 (7)	0.01640 (14)
C5	0.13401 (11)	0.81940 (9)	1.03721 (7)	0.01883 (15)
H5A	0.0272	0.8665	1.0283	0.023*
C6	0.22794 (12)	0.84237 (9)	1.11351 (7)	0.01903 (15)
H6A	0.1821	0.9037	1.1556	0.023*
C7	0.39036 (11)	0.77416 (8)	1.12736 (7)	0.01561 (14)
C8	0.45494 (11)	0.68414 (8)	1.06158 (7)	0.01569 (14)
H8A	0.5638	0.6392	1.0679	0.019*
C9	0.36033 (11)	0.65989 (8)	0.98659 (7)	0.01643 (14)
H9A	0.4061	0.5984	0.9445	0.020*
C10	0.49455 (13)	0.79371 (8)	1.21069 (7)	0.01946 (16)
H10A	0.5707	0.7175	1.2312	0.023*
H10B	0.4157	0.8096	1.2778	0.023*
C11	0.60476 (11)	0.90032 (8)	1.16960 (7)	0.01771 (15)
H11A	0.6727	0.8897	1.0966	0.021*
C12	0.49358 (13)	1.02704 (9)	1.15505 (8)	0.02153 (16)
H12A	0.5671	1.0909	1.1330	0.032*
H12B	0.4201	1.0371	1.2246	0.032*
H12C	0.4236	1.0329	1.0984	0.032*
C15	0.52183 (11)	0.75344 (8)	0.65702 (7)	0.01516 (14)
H15A	0.5176	0.8354	0.6196	0.018*
C16	0.68701 (10)	0.67289 (8)	0.65650 (7)	0.01452 (13)
C17	0.70399 (11)	0.55401 (8)	0.72377 (7)	0.01873 (15)
H17A	0.6074	0.5249	0.7704	0.022*
C18	0.86260 (12)	0.48024 (9)	0.72112 (8)	0.02101 (16)
H18A	0.8731	0.4024	0.7669	0.025*
C19	1.00817 (11)	0.52267 (8)	0.64930 (7)	0.01772 (15)
C20	0.99354 (11)	0.63973 (8)	0.58088 (7)	0.01699 (14)
H20A	1.0895	0.6678	0.5327	0.020*
C21	0.83293 (11)	0.71389 (8)	0.58586 (7)	0.01655 (14)
H21A	0.8229	0.7924	0.5411	0.020*
C22	1.30675 (12)	0.47650 (9)	0.57506 (8)	0.02174 (16)
H22A	1.3986	0.4081	0.5787	0.033*
H22B	1.3432	0.5464	0.5936	0.033*
H22C	1.2787	0.4981	0.5007	0.033*
H1N1	−0.0570 (19)	0.9791 (14)	0.6181 (12)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01509 (9)	0.02322 (11)	0.01447 (9)	0.00021 (7)	−0.00279 (6)	−0.00051 (7)
O1	0.0149 (3)	0.0231 (3)	0.0274 (3)	0.0035 (2)	−0.0003 (2)	0.0004 (3)
N1	0.0139 (3)	0.0221 (3)	0.0159 (3)	0.0014 (3)	−0.0040 (2)	−0.0045 (2)
N2	0.0143 (3)	0.0277 (4)	0.0161 (3)	−0.0012 (3)	−0.0027 (2)	−0.0057 (3)
N3	0.0122 (3)	0.0167 (3)	0.0142 (3)	−0.0006 (2)	−0.0029 (2)	−0.0028 (2)
N4	0.0137 (3)	0.0163 (3)	0.0160 (3)	0.0004 (2)	−0.0041 (2)	−0.0028 (2)
C1	0.0137 (3)	0.0164 (3)	0.0148 (3)	−0.0007 (3)	−0.0043 (2)	−0.0037 (3)
C2	0.0133 (3)	0.0229 (4)	0.0148 (3)	−0.0038 (3)	−0.0024 (2)	−0.0041 (3)
C3	0.0142 (5)	0.0172 (6)	0.0143 (4)	−0.0034 (4)	−0.0019 (3)	−0.0028 (4)
C14	0.0181 (4)	0.0339 (6)	0.0210 (4)	−0.0111 (4)	−0.0002 (3)	−0.0054 (4)
C3A	0.018 (6)	0.017 (6)	0.026 (6)	−0.002 (5)	−0.008 (4)	0.002 (5)
C14A	0.044 (8)	0.047 (8)	0.025 (5)	−0.025 (6)	−0.012 (5)	0.003 (5)
C13	0.0234 (4)	0.0274 (5)	0.0288 (4)	−0.0026 (4)	−0.0101 (4)	−0.0098 (4)
C4	0.0156 (3)	0.0199 (4)	0.0137 (3)	−0.0054 (3)	−0.0023 (3)	−0.0007 (3)
C5	0.0148 (3)	0.0208 (4)	0.0198 (4)	−0.0007 (3)	−0.0028 (3)	−0.0029 (3)
C6	0.0184 (4)	0.0192 (4)	0.0192 (3)	−0.0010 (3)	−0.0015 (3)	−0.0056 (3)
C7	0.0182 (3)	0.0152 (3)	0.0134 (3)	−0.0034 (3)	−0.0030 (3)	−0.0012 (2)
C8	0.0152 (3)	0.0154 (3)	0.0163 (3)	−0.0019 (3)	−0.0035 (3)	−0.0020 (3)
C9	0.0173 (3)	0.0169 (3)	0.0155 (3)	−0.0033 (3)	−0.0018 (3)	−0.0038 (3)
C10	0.0255 (4)	0.0182 (4)	0.0164 (3)	−0.0046 (3)	−0.0076 (3)	−0.0019 (3)
C11	0.0176 (4)	0.0198 (4)	0.0170 (3)	−0.0031 (3)	−0.0031 (3)	−0.0057 (3)
C12	0.0224 (4)	0.0187 (4)	0.0234 (4)	−0.0041 (3)	−0.0035 (3)	−0.0028 (3)
C15	0.0154 (3)	0.0146 (3)	0.0162 (3)	−0.0009 (3)	−0.0050 (3)	−0.0032 (3)
C16	0.0137 (3)	0.0147 (3)	0.0153 (3)	−0.0011 (3)	−0.0032 (2)	−0.0027 (2)
C17	0.0154 (3)	0.0185 (4)	0.0188 (3)	−0.0009 (3)	−0.0010 (3)	0.0015 (3)
C18	0.0173 (4)	0.0188 (4)	0.0220 (4)	0.0000 (3)	−0.0008 (3)	0.0031 (3)
C19	0.0148 (3)	0.0176 (4)	0.0194 (3)	0.0000 (3)	−0.0025 (3)	−0.0025 (3)
C20	0.0146 (3)	0.0163 (3)	0.0196 (3)	−0.0032 (3)	−0.0013 (3)	−0.0027 (3)
C21	0.0164 (3)	0.0142 (3)	0.0187 (3)	−0.0027 (3)	−0.0030 (3)	−0.0018 (3)
C22	0.0152 (4)	0.0257 (4)	0.0237 (4)	0.0000 (3)	−0.0010 (3)	−0.0072 (3)

S1—C1	1.6852 (8)	C5—H5A	0.93
O1—C19	1.3597 (11)	C6—C7	1.4009 (12)
O1—C22	1.4300 (11)	C6—H6A	0.93
N1—C1	1.3399 (11)	C7—C8	1.3932 (12)
N1—N2	1.3781 (11)	C7—C10	1.5098 (12)
N1—H1N1	0.872 (15)	C8—C9	1.3935 (11)
N2—C2	1.3033 (12)	C8—H8A	0.93
N3—C1	1.3813 (10)	C9—H9A	0.93
N3—C2	1.3818 (11)	C10—C11	1.5392 (12)
N3—N4	1.3968 (10)	C10—H10A	0.97
N4—C15	1.2885 (11)	C10—H10B	0.97
C2—C3A	1.425 (15)	C11—C12	1.5257 (13)
C2—C3	1.5075 (16)	C11—H11A	0.98
C3—C4	1.5307 (15)	C12—H12A	0.96
C3—C14	1.5360 (17)	C12—H12B	0.96
C3—H3A	0.98	C12—H12C	0.96
C14—H14A	0.96	C15—C16	1.4561 (12)
C14—H14B	0.96	C15—H15A	0.93
C14—H14C	0.96	C16—C21	1.3945 (11)
C3A—C14A	1.47 (2)	C16—C17	1.4068 (12)
C3A—C4	1.492 (14)	C17—C18	1.3793 (12)
C3A—H3AA	0.98	C17—H17A	0.93
C14A—H14D	0.96	C18—C19	1.4038 (12)
C14A—H14E	0.96	C18—H18A	0.93
C14A—H14F	0.96	C19—C20	1.3958 (12)
C13—C11	1.5295 (13)	C20—C21	1.3935 (12)
C13—H13A	0.96	C20—H20A	0.930
C13—H13B	0.96	C21—H21A	0.93
C13—H13C	0.96	C22—H22A	0.96
C4—C9	1.3876 (12)	C22—H22B	0.96
C4—C5	1.3983 (13)	C22—H22C	0.96
C5—C6	1.3968 (12)
C19—O1—C22	117.43 (7)	C8—C7—C10	119.69 (8)
C1—N1—N2	113.71 (7)	C6—C7—C10	122.67 (8)
C1—N1—H1N1	127.2 (10)	C7—C8—C9	121.59 (8)
N2—N1—H1N1	118.4 (10)	C7—C8—H8A	119.2
C2—N2—N1	104.40 (7)	C9—C8—H8A	119.2
C1—N3—C2	108.44 (7)	C4—C9—C8	120.72 (8)
C1—N3—N4	129.86 (7)	C4—C9—H9A	119.6
C2—N3—N4	120.95 (7)	C8—C9—H9A	119.6
C15—N4—N3	115.36 (7)	C7—C10—C11	115.19 (7)
N1—C1—N3	102.87 (7)	C7—C10—H10A	108.5
N1—C1—S1	127.94 (7)	C11—C10—H10A	108.5
N3—C1—S1	129.04 (6)	C7—C10—H10B	108.5
N2—C2—N3	110.38 (7)	C11—C10—H10B	108.5
N2—C2—C3A	111.2 (7)	H10A—C10—H10B	107.5
N3—C2—C3A	137.2 (6)	C12—C11—C13	110.49 (7)
N2—C2—C3	126.82 (9)	C12—C11—C10	112.14 (7)
N3—C2—C3	122.71 (9)	C13—C11—C10	109.89 (7)
C2—C3—C4	111.44 (10)	C12—C11—H11A	108.1
C2—C3—C14	109.65 (11)	C13—C11—H11A	108.1
C4—C3—C14	112.38 (9)	C10—C11—H11A	108.1
C2—C3—H3A	107.7	C11—C12—H12A	109.5
C4—C3—H3A	107.7	C11—C12—H12B	109.5
C14—C3—H3A	107.7	H12A—C12—H12B	109.5
C2—C3A—C14A	103.8 (12)	C11—C12—H12C	109.5
C2—C3A—C4	118.7 (10)	H12A—C12—H12C	109.5
C14A—C3A—C4	105.1 (10)	H12B—C12—H12C	109.5
C2—C3A—H3AA	109.6	N4—C15—C16	119.97 (7)
C14A—C3A—H3AA	109.6	N4—C15—H15A	120.0
C4—C3A—H3AA	109.6	C16—C15—H15A	120.0
C3A—C14A—H14D	109.5	C21—C16—C17	118.75 (8)
C3A—C14A—H14E	109.5	C21—C16—C15	119.08 (7)
H14D—C14A—H14E	109.5	C17—C16—C15	122.16 (7)
C3A—C14A—H14F	109.5	C18—C17—C16	120.57 (8)
H14D—C14A—H14F	109.5	C18—C17—H17A	119.7
H14E—C14A—H14F	109.5	C16—C17—H17A	119.7
C11—C13—H13A	109.5	C17—C18—C19	119.99 (8)
C11—C13—H13B	109.5	C17—C18—H18A	120.0
H13A—C13—H13B	109.5	C19—C18—H18A	120.0
C11—C13—H13C	109.5	O1—C19—C20	124.62 (8)
H13A—C13—H13C	109.5	O1—C19—C18	115.08 (8)
H13B—C13—H13C	109.5	C20—C19—C18	120.30 (8)
C9—C4—C5	118.33 (8)	C21—C20—C19	118.99 (8)
C9—C4—C3A	137.9 (7)	C21—C20—H20A	120.5
C5—C4—C3A	103.8 (7)	C19—C20—H20A	120.5
C9—C4—C3	119.03 (9)	C20—C21—C16	121.39 (8)
C5—C4—C3	122.60 (9)	C20—C21—H21A	119.3
C6—C5—C4	120.85 (8)	C16—C21—H21A	119.3
C6—C5—H5A	119.6	O1—C22—H22A	109.5
C4—C5—H5A	119.6	O1—C22—H22B	109.5
C5—C6—C7	120.84 (8)	H22A—C22—H22B	109.5
C5—C6—H6A	119.6	O1—C22—H22C	109.5
C7—C6—H6A	119.6	H22A—C22—H22C	109.5
C8—C7—C6	117.63 (8)	H22B—C22—H22C	109.5
C1—N1—N2—C2	1.66 (10)	C14—C3—C4—C9	129.28 (11)
C1—N3—N4—C15	41.04 (12)	C2—C3—C4—C5	75.33 (12)
C2—N3—N4—C15	−150.12 (8)	C14—C3—C4—C5	−48.21 (15)
N2—N1—C1—N3	−3.89 (9)	C2—C3—C4—C3A	62.7 (18)
N2—N1—C1—S1	171.98 (6)	C14—C3—C4—C3A	−60.8 (18)
C2—N3—C1—N1	4.54 (9)	C9—C4—C5—C6	−1.79 (13)
N4—N3—C1—N1	174.46 (8)	C3A—C4—C5—C6	179.9 (6)
C2—N3—C1—S1	−171.28 (7)	C3—C4—C5—C6	175.71 (9)
N4—N3—C1—S1	−1.35 (13)	C4—C5—C6—C7	1.00 (13)
N1—N2—C2—N3	1.41 (9)	C5—C6—C7—C8	0.72 (12)
N1—N2—C2—C3A	171.1 (7)	C5—C6—C7—C10	−178.53 (8)
N1—N2—C2—C3	−175.19 (9)	C6—C7—C8—C9	−1.67 (12)
C1—N3—C2—N2	−3.89 (10)	C10—C7—C8—C9	177.61 (8)
N4—N3—C2—N2	−174.88 (7)	C5—C4—C9—C8	0.86 (12)
C1—N3—C2—C3A	−169.6 (10)	C3A—C4—C9—C8	178.3 (8)
N4—N3—C2—C3A	19.4 (10)	C3—C4—C9—C8	−176.73 (9)
C1—N3—C2—C3	172.88 (9)	C7—C8—C9—C4	0.89 (12)
N4—N3—C2—C3	1.89 (13)	C8—C7—C10—C11	96.95 (10)
N2—C2—C3—C4	−107.03 (11)	C6—C7—C10—C11	−83.81 (11)
N3—C2—C3—C4	76.76 (13)	C7—C10—C11—C12	68.35 (10)
C3A—C2—C3—C4	−65.9 (18)	C7—C10—C11—C13	−168.35 (8)
N2—C2—C3—C14	18.05 (15)	N3—N4—C15—C16	−179.10 (7)
N3—C2—C3—C14	−158.17 (9)	N4—C15—C16—C21	170.31 (8)
C3A—C2—C3—C14	59.2 (18)	N4—C15—C16—C17	−8.71 (12)
N2—C2—C3A—C14A	113.0 (10)	C21—C16—C17—C18	0.99 (13)
N3—C2—C3A—C14A	−81.3 (12)	C15—C16—C17—C18	−179.99 (8)
C3—C2—C3A—C14A	−32.6 (14)	C16—C17—C18—C19	−1.21 (14)
N2—C2—C3A—C4	−130.8 (10)	C22—O1—C19—C20	−4.71 (13)
N3—C2—C3A—C4	34.9 (18)	C22—O1—C19—C18	175.19 (8)
C3—C2—C3A—C4	83.6 (19)	C17—C18—C19—O1	−179.50 (8)
C2—C3A—C4—C9	−73.2 (14)	C17—C18—C19—C20	0.41 (14)
C14A—C3A—C4—C9	42.3 (15)	O1—C19—C20—C21	−179.51 (8)
C2—C3A—C4—C5	104.5 (11)	C18—C19—C20—C21	0.59 (13)
C14A—C3A—C4—C5	−140.0 (10)	C19—C20—C21—C16	−0.81 (13)
C2—C3A—C4—C3	−86 (2)	C17—C16—C21—C20	0.03 (13)
C14A—C3A—C4—C3	29.1 (12)	C15—C16—C21—C20	−179.02 (8)
C2—C3—C4—C9	−107.18 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1i	0.87 (2)	2.39 (2)	3.2482 (8)	168 (1)
C15—H15A···S1	0.93	2.66	3.1947 (9)	117
C13—H13A···Cg1ii	0.96	2.77	3.5416 (12)	138
C12—H12A···Cg2ii	0.96	2.73	3.5417 (11)	142
C18—H18A···Cg2iii	0.93	2.80	3.5903 (10)	144
C22—H22C···Cg3iv	0.96	2.78	3.5783 (10)	142
C14A—H14D···Cg3v	0.96	2.88	3.769 (13)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1i	0.87 (2)	2.39 (2)	3.2482 (8)	168 (1)
C15—H15A⋯S1	0.93	2.66	3.1947 (9)	117
C13—H13A⋯Cg1ii	0.96	2.77	3.5416 (12)	138
C12—H12A⋯Cg2ii	0.96	2.73	3.5417 (11)	142
C18—H18A⋯Cg2iii	0.93	2.80	3.5903 (10)	144
C22—H22C⋯Cg3iv	0.96	2.78	3.5783 (10)	142
C14A—H14D⋯Cg3v	0.96	2.88	3.769 (13)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of the N1/N2/C2/N3/C1 ring, Cg2 is the centroid of the C4–C9 ring and Cg3 is the centroid of the C16–C21 ring.