4,4,6-Trimethyl-1-(3-methyl-phen-yl)-3,4-dihydro-pyrimidine-2(1H)-thione.

The asymmetric unit of the title compound, C(14)H(18)N(2)S, contains two independent and conformationally similar mol-ecules, which form cyclic dimers via inter-molecular hydrogen bonds of the type N-H⋯S [graph set R(2) (2)(8)]. The structure is iso-morphous with that of one of the polymorphs of 4,4,6-tri-methyl-1-phenyl-3,4-dihydro-pyrimidine-2(1H)-thione [Yam-in et al. (2005 ▶). Acta Cryst. E61, o55-o57].

Related literature

For the biological activity of pyrimidine-2-thio­nes, see: Alam et al. (2005 ▶); Sriram et al. (2006 ▶); Swamy et al. (2005 ▶). For related structures, see: Yamin et al. (2005 ▶); Ismail et al. (2007 ▶). For graph-set analysis, see Etter et al. (1990 ▶).

Experimental

Crystal data

C14H18N2S

M = 246.36

Orthorhombic,

a = 10.5904 (3) Å

b = 16.9189 (5) Å

c = 30.5713 (10) Å

V = 5477.7 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.14 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.970, T max = 0.983

19135 measured reflections

4830 independent reflections

3231 reflections with I > 2.0σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.115

S = 1.04

4830 reflections

315 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536810004708/zs2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004708/zs2028Isup2.hkl

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

C14H18N2S	F(000) = 2112
Mr = 246.36	Dx = 1.195 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8634 reflections
a = 10.5904 (3) Å	θ = 1.0–25.3°
b = 16.9189 (5) Å	µ = 0.22 mm−1
c = 30.5713 (10) Å	T = 173 K
V = 5477.7 (3) Å3	Block, colorless
Z = 16	0.14 × 0.12 × 0.08 mm

Bruker APEXII CCD diffractometer	4830 independent reflections
Radiation source: fine-focus sealed tube	3231 reflections with I > 2.0σ(I)
graphite	Rint = 0.041
φ & ω scans	θmax = 25.3°, θmin = 2.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
Tmin = 0.970, Tmax = 0.983	k = −20→20
19135 measured reflections	l = −36→36

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.038P)2 + 3.05P] where P = (Fo2 + 2Fc2)/3
4830 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

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
S1	0.85314 (7)	0.07897 (4)	0.325070 (19)	0.03644 (19)
S2	0.84290 (7)	0.24913 (4)	0.43316 (2)	0.03863 (19)
N1	0.75860 (19)	0.22309 (11)	0.32616 (6)	0.0343 (5)
H1N	0.7579	0.2164	0.3547	0.041*
N2	0.76802 (18)	0.16559 (11)	0.25790 (6)	0.0305 (5)
N3	0.7806 (2)	0.09853 (11)	0.43444 (6)	0.0376 (5)
H3N	0.7897	0.1032	0.4060	0.045*
N4	0.7743 (2)	0.16054 (12)	0.50157 (6)	0.0354 (5)
C1	0.7907 (2)	0.16081 (13)	0.30203 (7)	0.0285 (6)
C2	0.7240 (2)	0.30212 (14)	0.30983 (8)	0.0327 (6)
C3	0.6741 (2)	0.29264 (14)	0.26468 (8)	0.0365 (6)
H3	0.6220	0.3332	0.2530	0.044*
C4	0.6990 (2)	0.23009 (14)	0.23982 (8)	0.0325 (6)
C5	0.6260 (3)	0.33607 (17)	0.34098 (9)	0.0513 (8)
H5A	0.6052	0.3902	0.3321	0.062*
H5B	0.6601	0.3365	0.3708	0.062*
H5C	0.5496	0.3034	0.3401	0.062*
C6	0.8409 (3)	0.35435 (16)	0.31010 (10)	0.0476 (7)
H6A	0.8182	0.4077	0.3003	0.057*
H6B	0.9045	0.3321	0.2903	0.057*
H6C	0.8753	0.3569	0.3398	0.057*
C7	0.6571 (3)	0.22143 (16)	0.19344 (8)	0.0440 (7)
H7A	0.6124	0.2694	0.1843	0.053*
H7B	0.6003	0.1759	0.1909	0.053*
H7C	0.7309	0.2133	0.1746	0.053*
C8	0.8098 (2)	0.10194 (14)	0.23002 (7)	0.0293 (6)
C9	0.7269 (2)	0.04236 (14)	0.21939 (7)	0.0316 (6)
H9	0.6433	0.0432	0.2306	0.038*
C10	0.7653 (2)	−0.01925 (14)	0.19210 (8)	0.0346 (6)
C11	0.8885 (3)	−0.01932 (15)	0.17714 (8)	0.0380 (6)
H11	0.9167	−0.0617	0.1592	0.046*
C12	0.9715 (2)	0.04068 (16)	0.18757 (8)	0.0386 (6)
H12	1.0554	0.0397	0.1766	0.046*
C13	0.9320 (2)	0.10269 (15)	0.21418 (7)	0.0339 (6)
H13	0.9879	0.1447	0.2213	0.041*
C14	0.6721 (3)	−0.08216 (16)	0.17965 (9)	0.0494 (8)
H14A	0.7167	−0.1264	0.1658	0.059*
H14B	0.6104	−0.0602	0.1591	0.059*
H14C	0.6283	−0.1009	0.2059	0.059*
C15	0.7974 (2)	0.16412 (14)	0.45766 (8)	0.0325 (6)
C16	0.7484 (3)	0.01867 (14)	0.45061 (8)	0.0390 (7)
C17	0.7067 (3)	0.02656 (17)	0.49684 (9)	0.0549 (8)
H17	0.6667	−0.0176	0.5101	0.066*
C18	0.7217 (3)	0.09111 (15)	0.52074 (8)	0.0420 (7)
C19	0.8654 (3)	−0.03424 (16)	0.44798 (10)	0.0569 (8)
H19A	0.8435	−0.0878	0.4576	0.068*
H19B	0.9317	−0.0129	0.4670	0.068*
H19C	0.8959	−0.0359	0.4177	0.068*
C20	0.6454 (3)	−0.01520 (17)	0.42148 (10)	0.0532 (8)
H20A	0.6238	−0.0686	0.4314	0.064*
H20B	0.6756	−0.0174	0.3912	0.064*
H20C	0.5704	0.0186	0.4230	0.064*
C21	0.6857 (4)	0.09640 (19)	0.56755 (10)	0.0709 (10)
H21A	0.6561	0.0447	0.5777	0.085*
H21B	0.6180	0.1354	0.5710	0.085*
H21C	0.7591	0.1127	0.5849	0.085*
C22	0.8055 (2)	0.22713 (14)	0.52939 (8)	0.0331 (6)
C23	0.7123 (2)	0.27825 (15)	0.54251 (8)	0.0355 (6)
H23	0.6288	0.2718	0.5317	0.043*
C24	0.7391 (3)	0.33970 (15)	0.57156 (8)	0.0381 (6)
C25	0.8616 (3)	0.34748 (16)	0.58649 (8)	0.0425 (7)
H25	0.8815	0.3887	0.6064	0.051*
C26	0.9557 (3)	0.29648 (17)	0.57300 (8)	0.0464 (7)
H26	1.0396	0.3033	0.5833	0.056*
C27	0.9278 (3)	0.23536 (16)	0.54441 (8)	0.0403 (7)
H27	0.9918	0.1997	0.5353	0.048*
C28	0.6363 (3)	0.39498 (17)	0.58604 (10)	0.0541 (8)
H28A	0.6659	0.4260	0.6111	0.065*
H28B	0.5617	0.3644	0.5945	0.065*
H28C	0.6144	0.4306	0.5619	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0510 (4)	0.0257 (3)	0.0326 (3)	0.0049 (3)	−0.0024 (3)	0.0000 (3)
S2	0.0582 (5)	0.0254 (3)	0.0322 (3)	−0.0035 (3)	−0.0002 (3)	0.0002 (3)
N1	0.0497 (13)	0.0252 (11)	0.0281 (10)	0.0039 (10)	0.0008 (10)	−0.0014 (9)
N2	0.0352 (12)	0.0272 (11)	0.0292 (10)	0.0041 (10)	−0.0024 (10)	−0.0019 (9)
N3	0.0615 (15)	0.0240 (11)	0.0274 (11)	−0.0043 (11)	0.0009 (11)	−0.0011 (9)
N4	0.0493 (14)	0.0276 (11)	0.0291 (11)	−0.0034 (11)	0.0026 (10)	−0.0016 (9)
C1	0.0295 (13)	0.0243 (13)	0.0318 (13)	−0.0033 (11)	0.0000 (11)	−0.0012 (10)
C2	0.0375 (15)	0.0245 (13)	0.0362 (13)	0.0026 (12)	−0.0003 (12)	−0.0029 (11)
C3	0.0383 (15)	0.0272 (14)	0.0439 (15)	0.0046 (12)	−0.0074 (13)	0.0029 (12)
C4	0.0326 (14)	0.0304 (14)	0.0345 (14)	0.0000 (12)	−0.0033 (12)	0.0016 (11)
C5	0.0586 (19)	0.0457 (18)	0.0495 (16)	0.0192 (16)	0.0048 (15)	−0.0015 (14)
C6	0.0503 (18)	0.0360 (16)	0.0564 (17)	−0.0044 (14)	−0.0067 (15)	0.0013 (13)
C7	0.0522 (18)	0.0370 (16)	0.0427 (15)	0.0072 (14)	−0.0087 (14)	0.0001 (12)
C8	0.0337 (15)	0.0272 (13)	0.0270 (12)	0.0039 (12)	−0.0030 (11)	0.0003 (10)
C9	0.0310 (14)	0.0335 (14)	0.0304 (13)	0.0018 (12)	0.0000 (11)	0.0007 (11)
C10	0.0437 (16)	0.0299 (14)	0.0300 (13)	0.0001 (13)	−0.0069 (12)	0.0011 (11)
C11	0.0471 (17)	0.0375 (16)	0.0293 (13)	0.0127 (14)	−0.0058 (13)	−0.0053 (12)
C12	0.0360 (15)	0.0475 (17)	0.0324 (14)	0.0066 (14)	0.0006 (12)	−0.0001 (13)
C13	0.0338 (15)	0.0375 (15)	0.0305 (13)	−0.0008 (12)	−0.0011 (12)	−0.0006 (11)
C14	0.061 (2)	0.0392 (16)	0.0475 (16)	−0.0060 (15)	−0.0062 (15)	−0.0059 (13)
C15	0.0375 (15)	0.0285 (14)	0.0316 (13)	0.0011 (12)	−0.0027 (11)	−0.0003 (11)
C16	0.0558 (18)	0.0235 (14)	0.0378 (15)	−0.0044 (13)	0.0016 (14)	0.0008 (11)
C17	0.083 (2)	0.0356 (17)	0.0457 (17)	−0.0191 (17)	0.0134 (16)	0.0015 (13)
C18	0.0555 (18)	0.0337 (15)	0.0369 (14)	−0.0072 (14)	0.0043 (14)	0.0028 (12)
C19	0.067 (2)	0.0353 (17)	0.068 (2)	0.0020 (16)	−0.0107 (17)	0.0072 (15)
C20	0.060 (2)	0.0351 (16)	0.0645 (19)	−0.0108 (15)	−0.0136 (16)	0.0014 (14)
C21	0.114 (3)	0.054 (2)	0.0451 (17)	−0.026 (2)	0.0167 (19)	0.0044 (15)
C22	0.0427 (16)	0.0287 (14)	0.0278 (12)	−0.0003 (13)	0.0009 (12)	−0.0017 (10)
C23	0.0359 (15)	0.0386 (15)	0.0319 (13)	−0.0014 (13)	−0.0031 (12)	−0.0013 (12)
C24	0.0479 (17)	0.0339 (15)	0.0325 (13)	0.0029 (14)	0.0026 (13)	−0.0058 (12)
C25	0.0503 (18)	0.0429 (17)	0.0343 (14)	−0.0076 (15)	−0.0065 (14)	−0.0086 (12)
C26	0.0418 (17)	0.0542 (19)	0.0431 (16)	−0.0059 (16)	−0.0066 (14)	0.0004 (14)
C27	0.0400 (16)	0.0384 (16)	0.0425 (15)	0.0029 (13)	0.0002 (13)	−0.0008 (12)
C28	0.0571 (19)	0.0471 (18)	0.0580 (18)	0.0050 (16)	0.0054 (16)	−0.0155 (15)

S1—C1	1.688 (2)	C11—H11	0.9500
S2—C15	1.692 (2)	C12—C13	1.392 (3)
N1—C1	1.331 (3)	C12—H12	0.9500
N1—C2	1.473 (3)	C13—H13	0.9500
N1—H1N	0.8800	C14—H14A	0.9800
N2—C1	1.373 (3)	C14—H14B	0.9800
N2—C4	1.425 (3)	C14—H14C	0.9800
N2—C8	1.443 (3)	C16—C17	1.487 (4)
N3—C15	1.329 (3)	C16—C20	1.520 (4)
N3—C16	1.478 (3)	C16—C19	1.531 (4)
N3—H3N	0.8800	C17—C18	1.324 (4)
N4—C15	1.366 (3)	C17—H17	0.9500
N4—C18	1.426 (3)	C18—C21	1.484 (4)
N4—C22	1.450 (3)	C19—H19A	0.9800
C2—C3	1.487 (3)	C19—H19B	0.9800
C2—C5	1.521 (3)	C19—H19C	0.9800
C2—C6	1.521 (3)	C20—H20A	0.9800
C3—C4	1.329 (3)	C20—H20B	0.9800
C3—H3	0.9500	C20—H20C	0.9800
C4—C7	1.493 (3)	C21—H21A	0.9800
C5—H5A	0.9800	C21—H21B	0.9800
C5—H5B	0.9800	C21—H21C	0.9800
C5—H5C	0.9800	C22—C23	1.372 (3)
C6—H6A	0.9800	C22—C27	1.381 (3)
C6—H6B	0.9800	C23—C24	1.396 (3)
C6—H6C	0.9800	C23—H23	0.9500
C7—H7A	0.9800	C24—C25	1.382 (4)
C7—H7B	0.9800	C24—C28	1.501 (4)
C7—H7C	0.9800	C25—C26	1.381 (4)
C8—C9	1.376 (3)	C25—H25	0.9500
C8—C13	1.381 (3)	C26—C27	1.386 (4)
C9—C10	1.396 (3)	C26—H26	0.9500
C9—H9	0.9500	C27—H27	0.9500
C10—C11	1.382 (4)	C28—H28A	0.9800
C10—C14	1.501 (3)	C28—H28B	0.9800
C11—C12	1.380 (3)	C28—H28C	0.9800
C1—N1—C2	126.47 (19)	C10—C14—H14A	109.5
C1—N1—H1N	116.8	C10—C14—H14B	109.5
C2—N1—H1N	116.8	H14A—C14—H14B	109.5
C1—N2—C4	121.07 (19)	C10—C14—H14C	109.5
C1—N2—C8	118.86 (19)	H14A—C14—H14C	109.5
C4—N2—C8	119.99 (18)	H14B—C14—H14C	109.5
C15—N3—C16	128.0 (2)	N3—C15—N4	117.6 (2)
C15—N3—H3N	116.0	N3—C15—S2	120.77 (18)
C16—N3—H3N	116.0	N4—C15—S2	121.60 (18)
C15—N4—C18	120.7 (2)	N3—C16—C17	107.7 (2)
C15—N4—C22	120.1 (2)	N3—C16—C20	108.3 (2)
C18—N4—C22	119.22 (19)	C17—C16—C20	112.2 (2)
N1—C1—N2	117.0 (2)	N3—C16—C19	109.3 (2)
N1—C1—S1	121.21 (17)	C17—C16—C19	110.0 (2)
N2—C1—S1	121.80 (17)	C20—C16—C19	109.3 (2)
N1—C2—C3	107.76 (19)	C18—C17—C16	124.3 (2)
N1—C2—C5	107.5 (2)	C18—C17—H17	117.9
C3—C2—C5	112.3 (2)	C16—C17—H17	117.9
N1—C2—C6	108.8 (2)	C17—C18—N4	120.0 (2)
C3—C2—C6	110.9 (2)	C17—C18—C21	123.5 (3)
C5—C2—C6	109.4 (2)	N4—C18—C21	116.6 (2)
C4—C3—C2	123.1 (2)	C16—C19—H19A	109.5
C4—C3—H3	118.4	C16—C19—H19B	109.5
C2—C3—H3	118.4	H19A—C19—H19B	109.5
C3—C4—N2	119.3 (2)	C16—C19—H19C	109.5
C3—C4—C7	124.2 (2)	H19A—C19—H19C	109.5
N2—C4—C7	116.5 (2)	H19B—C19—H19C	109.5
C2—C5—H5A	109.5	C16—C20—H20A	109.5
C2—C5—H5B	109.5	C16—C20—H20B	109.5
H5A—C5—H5B	109.5	H20A—C20—H20B	109.5
C2—C5—H5C	109.5	C16—C20—H20C	109.5
H5A—C5—H5C	109.5	H20A—C20—H20C	109.5
H5B—C5—H5C	109.5	H20B—C20—H20C	109.5
C2—C6—H6A	109.5	C18—C21—H21A	109.5
C2—C6—H6B	109.5	C18—C21—H21B	109.5
H6A—C6—H6B	109.5	H21A—C21—H21B	109.5
C2—C6—H6C	109.5	C18—C21—H21C	109.5
H6A—C6—H6C	109.5	H21A—C21—H21C	109.5
H6B—C6—H6C	109.5	H21B—C21—H21C	109.5
C4—C7—H7A	109.5	C23—C22—C27	120.9 (2)
C4—C7—H7B	109.5	C23—C22—N4	119.8 (2)
H7A—C7—H7B	109.5	C27—C22—N4	119.2 (2)
C4—C7—H7C	109.5	C22—C23—C24	120.6 (2)
H7A—C7—H7C	109.5	C22—C23—H23	119.7
H7B—C7—H7C	109.5	C24—C23—H23	119.7
C9—C8—C13	121.5 (2)	C25—C24—C23	118.1 (2)
C9—C8—N2	119.4 (2)	C25—C24—C28	121.6 (2)
C13—C8—N2	119.2 (2)	C23—C24—C28	120.3 (2)
C8—C9—C10	120.1 (2)	C26—C25—C24	121.3 (2)
C8—C9—H9	119.9	C26—C25—H25	119.3
C10—C9—H9	119.9	C24—C25—H25	119.3
C11—C10—C9	118.3 (2)	C25—C26—C27	120.0 (3)
C11—C10—C14	122.4 (2)	C25—C26—H26	120.0
C9—C10—C14	119.3 (2)	C27—C26—H26	120.0
C12—C11—C10	121.6 (2)	C22—C27—C26	119.0 (3)
C12—C11—H11	119.2	C22—C27—H27	120.5
C10—C11—H11	119.2	C26—C27—H27	120.5
C11—C12—C13	119.9 (2)	C24—C28—H28A	109.5
C11—C12—H12	120.1	C24—C28—H28B	109.5
C13—C12—H12	120.1	H28A—C28—H28B	109.5
C8—C13—C12	118.7 (2)	C24—C28—H28C	109.5
C8—C13—H13	120.7	H28A—C28—H28C	109.5
C12—C13—H13	120.7	H28B—C28—H28C	109.5
C2—N1—C1—N2	−12.6 (4)	C16—N3—C15—N4	−5.1 (4)
C2—N1—C1—S1	168.88 (18)	C16—N3—C15—S2	176.2 (2)
C4—N2—C1—N1	−7.6 (3)	C18—N4—C15—N3	−6.2 (4)
C8—N2—C1—N1	175.5 (2)	C22—N4—C15—N3	172.5 (2)
C4—N2—C1—S1	170.90 (17)	C18—N4—C15—S2	172.50 (19)
C8—N2—C1—S1	−6.0 (3)	C22—N4—C15—S2	−8.8 (3)
C1—N1—C2—C3	25.6 (3)	C15—N3—C16—C17	13.6 (4)
C1—N1—C2—C5	146.8 (2)	C15—N3—C16—C20	135.1 (3)
C1—N1—C2—C6	−94.7 (3)	C15—N3—C16—C19	−105.9 (3)
N1—C2—C3—C4	−21.0 (3)	N3—C16—C17—C18	−12.5 (4)
C5—C2—C3—C4	−139.2 (3)	C20—C16—C17—C18	−131.6 (3)
C6—C2—C3—C4	98.0 (3)	C19—C16—C17—C18	106.6 (3)
C2—C3—C4—N2	5.3 (4)	C16—C17—C18—N4	3.8 (5)
C2—C3—C4—C7	−175.9 (2)	C16—C17—C18—C21	−176.6 (3)
C1—N2—C4—C3	11.0 (3)	C15—N4—C18—C17	6.8 (4)
C8—N2—C4—C3	−172.1 (2)	C22—N4—C18—C17	−171.9 (3)
C1—N2—C4—C7	−167.8 (2)	C15—N4—C18—C21	−172.8 (3)
C8—N2—C4—C7	9.1 (3)	C22—N4—C18—C21	8.5 (4)
C1—N2—C8—C9	94.8 (3)	C15—N4—C22—C23	100.7 (3)
C4—N2—C8—C9	−82.2 (3)	C18—N4—C22—C23	−80.6 (3)
C1—N2—C8—C13	−85.9 (3)	C15—N4—C22—C27	−83.1 (3)
C4—N2—C8—C13	97.1 (3)	C18—N4—C22—C27	95.6 (3)
C13—C8—C9—C10	0.1 (4)	C27—C22—C23—C24	−0.2 (4)
N2—C8—C9—C10	179.3 (2)	N4—C22—C23—C24	175.8 (2)
C8—C9—C10—C11	1.4 (3)	C22—C23—C24—C25	0.2 (4)
C8—C9—C10—C14	−177.9 (2)	C22—C23—C24—C28	−179.5 (2)
C9—C10—C11—C12	−1.8 (4)	C23—C24—C25—C26	0.4 (4)
C14—C10—C11—C12	177.4 (2)	C28—C24—C25—C26	−179.9 (3)
C10—C11—C12—C13	0.8 (4)	C24—C25—C26—C27	−0.9 (4)
C9—C8—C13—C12	−1.2 (4)	C23—C22—C27—C26	−0.2 (4)
N2—C8—C13—C12	179.5 (2)	N4—C22—C27—C26	−176.4 (2)
C11—C12—C13—C8	0.8 (3)	C25—C26—C27—C22	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S2	0.88	2.62	3.419 (2)	151
N3—H3N···S1	0.88	2.60	3.447 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S2	0.88	2.62	3.419 (2)	151
N3—H3N⋯S1	0.88	2.60	3.447 (2)	163