Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]-2-(cyclo-hexyl-sulfan-yl)acetamide.

In the title mol-ecule, C15H20N4OS2, the acetamido fragment is nearly coplanar with the pyridyl ring [C-N-C-C torsion angle = -4.1 (2)°], while the cyclo-hexyl-sulfanyl portion protrudes from this plane [N-C-C-S torsion angle = -40.8 (6)°]. In the crystal, alternating pairwise N-H⋯O and N-H⋯N hydrogen bonds across inversion centres form chains along [101], which are associated into stepped layers via offset π-π stacking between pyridyl rings [centroid-centroid distance = 3.566 (1) Å]. The cyclo-hexyl group and the two atoms of the S-C bond attached to it are disordered over two sets of sites with site-occupancy factors of 0.8845 (18) and 0.1155 (18).

Related literature

For the diverse biological properties of pyridine-containing compounds see: Patrick & Kinsman (1996 ▶); Hishmat et al. (1990 ▶); Paronikyan et al. (2002 ▶); Bernardino et al. (2007 ▶); Doshi et al. (1999 ▶); Jemmezi et al. (2014 ▶); Mamolo et al. (2004 ▶); Bhatt et al. (2001 ▶). For the structure of a related compound, see: Akkurt et al. (2014 ▶).

Experimental

Crystal data

C15H20N4OS2

M = 336.47

Monoclinic,

a = 7.2269 (8) Å

b = 24.655 (3) Å

c = 9.6933 (11) Å

β = 92.5330 (17)°

V = 1725.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 150 K

0.23 × 0.18 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.93, T max = 0.97

31462 measured reflections

4538 independent reflections

3713 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.02

4538 reflections

225 parameters

68 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814018534/bh2502sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018534/bh2502Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018534/bh2502Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018534/bh2502fig1.tif

The title mol­ecule showing displacement ellipsoids at the 50% probability level. Only the major component of the disorder is shown.

Click here for additional data file.

. DOI: 10.1107/S1600536814018534/bh2502fig2.tif

Perspective view of a portion of the hydrogen-bonded chain.

Click here for additional data file.

c . DOI: 10.1107/S1600536814018534/bh2502fig3.tif

Packing viewed down the c axis, showing the pairwise N—H⋯O hydrogen bonding and the offset π-stacking inter­actions as dashed lines.

CCDC reference: 1019463

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

C15H20N4OS2	Dx = 1.295 Mg m−3
Mr = 336.47	Melting point: 463 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2269 (8) Å	Cell parameters from 9975 reflections
b = 24.655 (3) Å	θ = 2.3–29.0°
c = 9.6933 (11) Å	µ = 0.32 mm−1
β = 92.5330 (17)°	T = 150 K
V = 1725.5 (3) Å3	Plate, colourless
Z = 4	0.23 × 0.18 × 0.08 mm
F(000) = 712

Bruker SMART APEX CCD diffractometer	4538 independent reflections
Radiation source: fine-focus sealed tube	3713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 8.3660 pixels mm-1	θmax = 29.0°, θmin = 2.3°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −33→33
Tmin = 0.93, Tmax = 0.97	l = −13→13
31462 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)] = 0.040	Hydrogen site location: mixed
wR(F2) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.7171P] where P = (Fo2 + 2Fc2)/3
4538 reflections	(Δ/σ)max = 0.006
225 parameters	Δρmax = 0.36 e Å−3
68 restraints	Δρmin = −0.26 e Å−3
0 constraints

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 40 sec/frame.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.12721 (5)	0.61034 (2)	0.34743 (4)	0.03110 (11)
O1	0.91811 (16)	0.53918 (5)	0.71493 (12)	0.0356 (3)
N1	0.3292 (2)	0.54925 (6)	0.04030 (14)	0.0378 (3)
N2	0.41788 (16)	0.59429 (5)	0.52327 (12)	0.0235 (2)
N3	0.72278 (17)	0.50958 (5)	0.23714 (13)	0.0287 (3)
H3A	0.6773	0.4994	0.1520	0.034*
H3B	0.8363	0.4940	0.2514	0.034*
N4	0.64424 (17)	0.58430 (5)	0.69315 (12)	0.0264 (3)
H4A	0.5680	0.6065	0.7397	0.032*
C1	0.35074 (19)	0.58641 (5)	0.39522 (15)	0.0227 (3)
C2	0.44875 (19)	0.55937 (5)	0.29318 (14)	0.0218 (3)
C3	0.62544 (18)	0.53707 (5)	0.32894 (14)	0.0222 (3)
C4	0.69559 (19)	0.54512 (6)	0.46531 (14)	0.0237 (3)
H4	0.8137	0.5314	0.4948	0.028*
C5	0.58845 (19)	0.57337 (6)	0.55479 (14)	0.0226 (3)
C6	0.37713 (19)	0.55438 (6)	0.15424 (15)	0.0258 (3)
C7	0.0634 (2)	0.64195 (7)	0.50548 (17)	0.0332 (3)
H7A	0.0792	0.6160	0.5817	0.050*
H7B	−0.0664	0.6535	0.4968	0.050*
H7C	0.1425	0.6736	0.5242	0.050*
C8	0.8003 (2)	0.56755 (6)	0.76461 (15)	0.0258 (3)
S2	0.74307 (10)	0.65352 (3)	0.94799 (6)	0.03506 (15)	0.8845 (18)
C9	0.8162 (10)	0.5850 (2)	0.9147 (11)	0.0327 (9)	0.8845 (18)
H9A	0.9470	0.5811	0.9481	0.039*	0.8845 (18)
H9B	0.7413	0.5600	0.9693	0.039*	0.8845 (18)
C10	0.9173 (2)	0.69109 (7)	0.85620 (18)	0.0303 (4)	0.8845 (18)
H10	0.9378	0.6717	0.7675	0.036*	0.8845 (18)
C11	0.8422 (3)	0.74748 (9)	0.8213 (3)	0.0504 (6)	0.8845 (18)
H11A	0.8143	0.7667	0.9075	0.061*	0.8845 (18)
H11B	0.7255	0.7441	0.7645	0.061*	0.8845 (18)
C12	0.9827 (4)	0.78041 (10)	0.7421 (3)	0.0535 (6)	0.8845 (18)
H12A	1.0040	0.7625	0.6527	0.064*	0.8845 (18)
H12B	0.9323	0.8171	0.7225	0.064*	0.8845 (18)
C13	1.1633 (4)	0.78515 (11)	0.8244 (3)	0.0600 (7)	0.8845 (18)
H13A	1.1437	0.8053	0.9110	0.072*	0.8845 (18)
H13B	1.2532	0.8057	0.7707	0.072*	0.8845 (18)
C14	1.2412 (3)	0.72892 (12)	0.8587 (3)	0.0629 (7)	0.8845 (18)
H14A	1.3574	0.7327	0.9159	0.075*	0.8845 (18)
H14B	1.2708	0.7102	0.7721	0.075*	0.8845 (18)
C15	1.1027 (3)	0.69463 (11)	0.9368 (3)	0.0555 (6)	0.8845 (18)
H15A	1.1534	0.6577	0.9517	0.067*	0.8845 (18)
H15B	1.0842	0.7111	1.0284	0.067*	0.8845 (18)
S2A	0.6907 (8)	0.6447 (2)	0.9744 (5)	0.03506 (15)	0.1155 (18)
C9A	0.833 (9)	0.589 (2)	0.918 (9)	0.0327 (9)	0.1155 (18)
H9A1	0.9638	0.6007	0.9302	0.039*	0.1155 (18)
H9A2	0.8151	0.5584	0.9817	0.039*	0.1155 (18)
C10A	0.8290 (17)	0.7034 (5)	0.9292 (12)	0.0303 (4)	0.1155 (18)
H10A	0.7526	0.7352	0.9560	0.036*	0.1155 (18)
C11A	0.854 (3)	0.7113 (6)	0.7781 (15)	0.0504 (6)	0.1155 (18)
H11C	0.7317	0.7120	0.7283	0.061*	0.1155 (18)
H11D	0.9259	0.6806	0.7420	0.061*	0.1155 (18)
C12A	0.955 (3)	0.7639 (8)	0.753 (3)	0.0535 (6)	0.1155 (18)
H12C	0.8818	0.7945	0.7879	0.064*	0.1155 (18)
H12D	0.9664	0.7690	0.6524	0.064*	0.1155 (18)
C13A	1.148 (3)	0.7645 (10)	0.8242 (19)	0.0600 (7)	0.1155 (18)
H13C	1.2163	0.7980	0.8013	0.072*	0.1155 (18)
H13D	1.2214	0.7326	0.7971	0.072*	0.1155 (18)
C14A	1.109 (2)	0.7627 (8)	0.9781 (18)	0.0629 (7)	0.1155 (18)
H14C	1.2265	0.7651	1.0337	0.075*	0.1155 (18)
H14D	1.0308	0.7941	1.0018	0.075*	0.1155 (18)
C15A	1.009 (2)	0.7104 (8)	1.013 (2)	0.0555 (6)	0.1155 (18)
H15C	1.0912	0.6792	0.9947	0.067*	0.1155 (18)
H15D	0.9836	0.7102	1.1120	0.067*	0.1155 (18)

	U11	U22	U33	U12	U13	U23
S1	0.02353 (18)	0.0410 (2)	0.0283 (2)	0.00880 (15)	−0.00329 (14)	−0.00609 (15)
O1	0.0297 (6)	0.0485 (7)	0.0281 (6)	0.0102 (5)	−0.0041 (4)	−0.0026 (5)
N1	0.0409 (8)	0.0456 (8)	0.0261 (7)	0.0097 (6)	−0.0061 (6)	−0.0053 (6)
N2	0.0222 (6)	0.0265 (6)	0.0217 (6)	0.0017 (4)	−0.0002 (4)	−0.0023 (5)
N3	0.0253 (6)	0.0402 (7)	0.0206 (6)	0.0068 (5)	−0.0003 (5)	−0.0054 (5)
N4	0.0270 (6)	0.0320 (6)	0.0201 (6)	0.0037 (5)	−0.0010 (5)	−0.0048 (5)
C1	0.0201 (6)	0.0235 (6)	0.0245 (7)	−0.0005 (5)	0.0002 (5)	−0.0004 (5)
C2	0.0222 (6)	0.0233 (6)	0.0199 (6)	0.0000 (5)	−0.0004 (5)	−0.0003 (5)
C3	0.0216 (6)	0.0239 (6)	0.0212 (6)	−0.0013 (5)	0.0023 (5)	0.0002 (5)
C4	0.0195 (6)	0.0288 (7)	0.0226 (7)	0.0012 (5)	−0.0007 (5)	−0.0013 (5)
C5	0.0225 (6)	0.0248 (6)	0.0204 (6)	−0.0018 (5)	−0.0012 (5)	−0.0007 (5)
C6	0.0242 (7)	0.0277 (7)	0.0253 (7)	0.0043 (5)	−0.0006 (5)	−0.0019 (5)
C7	0.0285 (7)	0.0363 (8)	0.0353 (8)	0.0062 (6)	0.0058 (6)	−0.0048 (7)
C8	0.0280 (7)	0.0270 (7)	0.0221 (7)	−0.0040 (5)	−0.0021 (5)	0.0018 (5)
S2	0.0358 (3)	0.0437 (3)	0.0258 (3)	0.0014 (2)	0.0031 (2)	−0.0104 (2)
C9	0.0430 (19)	0.0336 (14)	0.0210 (10)	−0.0013 (13)	−0.0052 (14)	0.0001 (11)
C10	0.0315 (9)	0.0308 (8)	0.0283 (9)	0.0031 (7)	−0.0019 (7)	−0.0059 (7)
C11	0.0486 (12)	0.0362 (10)	0.0669 (15)	0.0101 (9)	0.0078 (11)	−0.0019 (10)
C12	0.0639 (16)	0.0350 (14)	0.0615 (15)	0.0021 (12)	0.0024 (12)	0.0057 (13)
C13	0.0766 (17)	0.0525 (16)	0.0504 (13)	−0.0250 (15)	−0.0012 (12)	−0.0093 (13)
C14	0.0373 (12)	0.0873 (19)	0.0622 (16)	−0.0158 (12)	−0.0173 (11)	0.0164 (14)
C15	0.0405 (12)	0.0721 (16)	0.0521 (14)	−0.0090 (11)	−0.0170 (10)	0.0152 (12)
S2A	0.0358 (3)	0.0437 (3)	0.0258 (3)	0.0014 (2)	0.0031 (2)	−0.0104 (2)
C9A	0.0430 (19)	0.0336 (14)	0.0210 (10)	−0.0013 (13)	−0.0052 (14)	0.0001 (11)
C10A	0.0315 (9)	0.0308 (8)	0.0283 (9)	0.0031 (7)	−0.0019 (7)	−0.0059 (7)
C11A	0.0486 (12)	0.0362 (10)	0.0669 (15)	0.0101 (9)	0.0078 (11)	−0.0019 (10)
C12A	0.0639 (16)	0.0350 (14)	0.0615 (15)	0.0021 (12)	0.0024 (12)	0.0057 (13)
C13A	0.0766 (17)	0.0525 (16)	0.0504 (13)	−0.0250 (15)	−0.0012 (12)	−0.0093 (13)
C14A	0.0373 (12)	0.0873 (19)	0.0622 (16)	−0.0158 (12)	−0.0173 (11)	0.0164 (14)
C15A	0.0405 (12)	0.0721 (16)	0.0521 (14)	−0.0090 (11)	−0.0170 (10)	0.0152 (12)

S1—C1	1.7624 (14)	C12—C13	1.505 (4)
S1—C7	1.7972 (16)	C12—H12A	0.9900
O1—C8	1.2173 (18)	C12—H12B	0.9900
N1—C6	1.150 (2)	C13—C14	1.527 (4)
N2—C1	1.3269 (18)	C13—H13A	0.9900
N2—C5	1.3586 (18)	C13—H13B	0.9900
N3—C3	1.3422 (18)	C14—C15	1.535 (3)
N3—H3A	0.9101	C14—H14A	0.9900
N3—H3B	0.9104	C14—H14B	0.9900
N4—C8	1.3616 (19)	C15—H15A	0.9900
N4—C5	1.4093 (18)	C15—H15B	0.9900
N4—H4A	0.9098	S2A—C9A	1.807 (18)
C1—C2	1.4094 (19)	S2A—C10A	1.823 (12)
C2—C3	1.4190 (19)	C9A—H9A1	0.9900
C2—C6	1.427 (2)	C9A—H9A2	0.9900
C3—C4	1.4087 (19)	C10A—C11A	1.496 (13)
C4—C5	1.3770 (19)	C10A—C15A	1.511 (12)
C4—H4	0.9500	C10A—H10A	1.0000
C7—H7A	0.9800	C11A—C12A	1.512 (13)
C7—H7B	0.9800	C11A—H11C	0.9900
C7—H7C	0.9800	C11A—H11D	0.9900
C8—C9	1.516 (10)	C12A—C13A	1.529 (14)
C8—C9A	1.59 (8)	C12A—H12C	0.9900
S2—C9	1.803 (4)	C12A—H12D	0.9900
S2—C10	1.826 (2)	C13A—C14A	1.533 (14)
C9—H9A	0.9900	C13A—H13C	0.9900
C9—H9B	0.9900	C13A—H13D	0.9900
C10—C15	1.523 (3)	C14A—C15A	1.520 (13)
C10—C11	1.525 (3)	C14A—H14C	0.9900
C10—H10	1.0000	C14A—H14D	0.9900
C11—C12	1.532 (4)	C15A—H15C	0.9900
C11—H11A	0.9900	C15A—H15D	0.9900
C11—H11B	0.9900
C1—S1—C7	100.83 (7)	C12—C13—H13A	109.6
C1—N2—C5	116.45 (12)	C14—C13—H13A	109.6
C3—N3—H3A	124.2	C12—C13—H13B	109.6
C3—N3—H3B	127.4	C14—C13—H13B	109.6
H3A—N3—H3B	107.9	H13A—C13—H13B	108.1
C8—N4—C5	128.45 (12)	C13—C14—C15	111.4 (2)
C8—N4—H4A	115.9	C13—C14—H14A	109.3
C5—N4—H4A	115.6	C15—C14—H14A	109.3
N2—C1—C2	123.46 (13)	C13—C14—H14B	109.3
N2—C1—S1	119.33 (10)	C15—C14—H14B	109.3
C2—C1—S1	117.21 (11)	H14A—C14—H14B	108.0
C1—C2—C3	119.11 (12)	C10—C15—C14	110.86 (18)
C1—C2—C6	122.05 (12)	C10—C15—H15A	109.5
C3—C2—C6	118.83 (12)	C14—C15—H15A	109.5
N3—C3—C4	121.05 (13)	C10—C15—H15B	109.5
N3—C3—C2	121.74 (13)	C14—C15—H15B	109.5
C4—C3—C2	117.21 (12)	H15A—C15—H15B	108.1
C5—C4—C3	118.24 (13)	C9A—S2A—C10A	102 (3)
C5—C4—H4	120.9	C8—C9A—S2A	118 (4)
C3—C4—H4	120.9	C8—C9A—H9A1	107.7
N2—C5—C4	125.47 (13)	S2A—C9A—H9A1	107.7
N2—C5—N4	111.10 (12)	C8—C9A—H9A2	107.7
C4—C5—N4	123.44 (13)	S2A—C9A—H9A2	107.7
N1—C6—C2	176.06 (16)	H9A1—C9A—H9A2	107.1
S1—C7—H7A	109.5	C11A—C10A—C15A	111.7 (13)
S1—C7—H7B	109.5	C11A—C10A—S2A	115.5 (9)
H7A—C7—H7B	109.5	C15A—C10A—S2A	115.5 (9)
S1—C7—H7C	109.5	C11A—C10A—H10A	104.2
H7A—C7—H7C	109.5	C15A—C10A—H10A	104.2
H7B—C7—H7C	109.5	S2A—C10A—H10A	104.2
O1—C8—N4	123.44 (14)	C10A—C11A—C12A	110.5 (17)
O1—C8—C9	121.2 (3)	C10A—C11A—H11C	109.6
N4—C8—C9	115.3 (3)	C12A—C11A—H11C	109.6
O1—C8—C9A	119.2 (18)	C10A—C11A—H11D	109.6
N4—C8—C9A	117.3 (17)	C12A—C11A—H11D	109.6
C9—S2—C10	100.0 (3)	H11C—C11A—H11D	108.1
C8—C9—S2	115.3 (6)	C11A—C12A—C13A	111.9 (17)
C8—C9—H9A	108.4	C11A—C12A—H12C	109.2
S2—C9—H9A	108.4	C13A—C12A—H12C	109.2
C8—C9—H9B	108.4	C11A—C12A—H12D	109.2
S2—C9—H9B	108.4	C13A—C12A—H12D	109.2
H9A—C9—H9B	107.5	H12C—C12A—H12D	107.9
C15—C10—C11	110.98 (18)	C12A—C13A—C14A	103 (2)
C15—C10—S2	112.88 (14)	C12A—C13A—H13C	111.1
C11—C10—S2	108.92 (14)	C14A—C13A—H13C	111.1
C15—C10—H10	108.0	C12A—C13A—H13D	111.1
C11—C10—H10	108.0	C14A—C13A—H13D	111.1
S2—C10—H10	108.0	H13C—C13A—H13D	109.0
C10—C11—C12	110.92 (19)	C15A—C14A—C13A	110.5 (17)
C10—C11—H11A	109.5	C15A—C14A—H14C	109.6
C12—C11—H11A	109.5	C13A—C14A—H14C	109.6
C10—C11—H11B	109.5	C15A—C14A—H14D	109.6
C12—C11—H11B	109.5	C13A—C14A—H14D	109.6
H11A—C11—H11B	108.0	H14C—C14A—H14D	108.1
C13—C12—C11	110.7 (2)	C10A—C15A—C14A	112.5 (13)
C13—C12—H12A	109.5	C10A—C15A—H15C	109.1
C11—C12—H12A	109.5	C14A—C15A—H15C	109.1
C13—C12—H12B	109.5	C10A—C15A—H15D	109.1
C11—C12—H12B	109.5	C14A—C15A—H15D	109.1
H12A—C12—H12B	108.1	H15C—C15A—H15D	107.8
C12—C13—C14	110.3 (2)
C5—N2—C1—C2	−1.8 (2)	C10—S2—C9—C8	−65.2 (5)
C5—N2—C1—S1	177.97 (10)	C9—S2—C10—C15	−78.6 (4)
C7—S1—C1—N2	1.40 (13)	C9—S2—C10—C11	157.7 (4)
C7—S1—C1—C2	−178.84 (11)	C15—C10—C11—C12	56.0 (3)
N2—C1—C2—C3	2.8 (2)	S2—C10—C11—C12	−179.18 (18)
S1—C1—C2—C3	−176.92 (10)	C10—C11—C12—C13	−57.8 (3)
N2—C1—C2—C6	−176.20 (13)	C11—C12—C13—C14	57.8 (3)
S1—C1—C2—C6	4.05 (18)	C12—C13—C14—C15	−56.8 (3)
C1—C2—C3—N3	178.10 (13)	C11—C10—C15—C14	−54.6 (3)
C6—C2—C3—N3	−2.8 (2)	S2—C10—C15—C14	−177.19 (19)
C1—C2—C3—C4	−2.14 (19)	C13—C14—C15—C10	55.2 (3)
C6—C2—C3—C4	176.93 (13)	O1—C8—C9A—S2A	164 (3)
N3—C3—C4—C5	−179.59 (13)	N4—C8—C9A—S2A	−13 (6)
C2—C3—C4—C5	0.6 (2)	C10A—S2A—C9A—C8	−90 (5)
C1—N2—C5—C4	0.1 (2)	C9A—S2A—C10A—C11A	65 (3)
C1—N2—C5—N4	−179.93 (12)	C9A—S2A—C10A—C15A	−68 (3)
C3—C4—C5—N2	0.4 (2)	C15A—C10A—C11A—C12A	−51 (2)
C3—C4—C5—N4	−179.53 (13)	S2A—C10A—C11A—C12A	174.6 (14)
C8—N4—C5—N2	176.01 (14)	C10A—C11A—C12A—C13A	61 (3)
C8—N4—C5—C4	−4.1 (2)	C11A—C12A—C13A—C14A	−65 (3)
C5—N4—C8—O1	−0.2 (2)	C12A—C13A—C14A—C15A	62 (2)
C5—N4—C8—C9	−178.1 (4)	C11A—C10A—C15A—C14A	51 (2)
C5—N4—C8—C9A	176 (3)	S2A—C10A—C15A—C14A	−174.9 (14)
O1—C8—C9—S2	141.3 (3)	C13A—C14A—C15A—C10A	−58 (2)
N4—C8—C9—S2	−40.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1i	0.91	1.97	2.8792 (17)	179
N3—H3A···N1ii	0.91	2.22	3.0640 (19)	155
C4—H4···O1	0.95	2.24	2.8493 (18)	121
C7—H7A···O1iii	0.98	2.60	3.440 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1i	0.91	1.97	2.8792 (17)	179
N3—H3A⋯N1ii	0.91	2.22	3.0640 (19)	155

Symmetry codes: (i) ; (ii) .