2,3,4,6,7,8,9,10-Octa-hydro-pyrimido[1,2-a]azepin-1-ium 2-cyano-1-(2,6-dimethylanilino)-2-(phenyl-sulfonyl)ethenethiol-ate.

In the title compound, C(9)H(17)N(2) (+)·C(17)H(15)N(2)O(2)S(2) (-), the Csp(2)-N bonds in the tetra-hydro-pyrimidine ring of the cation are delocalized. The negative charge is localized on the S atom of the thione group. Cations and anions are linked by N-H⋯S inter-molecular hydrogen bonds.

Related literature

For related literature, see: Bürgi & Dunitz (1994 ▶); Fadda et al. (2000 ▶); Dorwald (2000 ▶); Lindeman et al. (2003 ▶); Perez et al. (2004 ▶); Zefirov et al. (1990 ▶).

Experimental

Crystal data

C9H17N2 +·C17H15N2O2S2 −

M = 496.68

Triclinic,

a = 8.3278 (5) Å

b = 11.348 (4) Å

c = 13.661 (3) Å

α = 104.03 (2)°

β = 92.517 (9)°

γ = 90.635 (12)°

V = 1250.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer

Absorption correction: none

11732 measured reflections

4319 independent reflections

3564 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.090

S = 1.10

4319 reflections

317 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998 ▶); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: XP (Siemens, 1998 ▶); software used to prepare material for publication: SHELXTL-Plus.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065518/av2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065518/av2006Isup2.hkl

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

C9H17N2+·C17H15N2O2S2–	Z = 2
Mr = 496.68	F000 = 528
Triclinic, P1	Dx = 1.319 Mg m−3
a = 8.3278 (5) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.348 (4) Å	Cell parameters from 9472 reflections
c = 13.661 (3) Å	θ = 2.8–31.9º
α = 104.03 (2)º	µ = 0.24 mm−1
β = 92.517 (9)º	T = 293 (2) K
γ = 90.635 (12)º	Block, colourless
V = 1250.9 (5) Å3	0.20 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur3 diffractometer	4319 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3564 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.014
Detector resolution: 16.1827 pixels mm-1	θmax = 25.0º
T = 293(2) K	θmin = 3.0º
ω–scans	h = −9→9
Absorption correction: none	k = −13→13
11732 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.043P)2 + 0.3755P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
4319 reflections	Δρmax = 0.33 e Å−3
317 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.12739 (5)	0.23234 (3)	0.07779 (3)	0.03153 (12)
S2	0.32290 (6)	0.09686 (4)	0.32967 (3)	0.04391 (14)
O1	0.21822 (14)	0.32333 (11)	0.04679 (9)	0.0437 (3)
O2	0.10480 (15)	0.11538 (10)	0.00763 (9)	0.0420 (3)
N1	0.17889 (17)	−0.00391 (12)	0.15248 (11)	0.0365 (3)
H1N	0.136 (2)	0.0021 (17)	0.0957 (16)	0.045 (5)*
N2	0.2919 (2)	0.41319 (14)	0.31254 (12)	0.0506 (4)
N3	0.40259 (16)	0.72438 (12)	0.50300 (10)	0.0363 (3)
N4	0.42004 (19)	0.85309 (15)	0.39899 (13)	0.0459 (4)
H4N	0.376 (3)	0.904 (2)	0.3749 (16)	0.057 (6)*
C1	0.21102 (18)	0.21136 (14)	0.19027 (12)	0.0309 (3)
C2	0.23091 (17)	0.09922 (14)	0.21630 (12)	0.0303 (3)
C3	0.20953 (19)	−0.12349 (14)	0.16308 (12)	0.0323 (3)
C4	0.3526 (2)	−0.17697 (15)	0.12811 (13)	0.0382 (4)
C5	0.3722 (3)	−0.29728 (17)	0.12940 (15)	0.0524 (5)
H5	0.4660	−0.3360	0.1062	0.063*
C6	0.2562 (3)	−0.35999 (17)	0.16407 (17)	0.0586 (6)
H6	0.2713	−0.4412	0.1637	0.070*
C7	0.1188 (3)	−0.30538 (17)	0.19914 (15)	0.0532 (5)
H7	0.0420	−0.3492	0.2239	0.064*
C8	0.0913 (2)	−0.18553 (16)	0.19868 (13)	0.0393 (4)
C9	−0.0614 (2)	−0.1257 (2)	0.23623 (17)	0.0623 (6)
H9C	−0.1219	−0.1788	0.2665	0.093*
H9B	−0.1239	−0.1088	0.1807	0.093*
H9A	−0.0361	−0.0511	0.2855	0.093*
C10	0.4806 (2)	−0.1070 (2)	0.09221 (17)	0.0587 (5)
H10C	0.5594	−0.1619	0.0591	0.088*
H10B	0.5311	−0.0495	0.1488	0.088*
H10A	0.4337	−0.0646	0.0456	0.088*
C11	0.25701 (19)	0.32106 (14)	0.25980 (12)	0.0337 (4)
C12	−0.06628 (19)	0.29086 (15)	0.10429 (12)	0.0343 (4)
C13	−0.1846 (2)	0.21876 (18)	0.12817 (14)	0.0472 (4)
H13	−0.1636	0.1392	0.1306	0.057*
C14	−0.3353 (2)	0.2659 (2)	0.14860 (16)	0.0600 (6)
H14	−0.4158	0.2181	0.1657	0.072*
C15	−0.3663 (3)	0.3824 (2)	0.14384 (17)	0.0665 (6)
H15	−0.4679	0.4136	0.1573	0.080*
C16	−0.2487 (3)	0.4526 (2)	0.11951 (19)	0.0653 (6)
H16	−0.2706	0.5319	0.1166	0.078*
C17	−0.0964 (2)	0.40779 (17)	0.09902 (15)	0.0473 (4)
H17	−0.0163	0.4560	0.0820	0.057*
C18	0.3354 (2)	0.69195 (18)	0.59082 (14)	0.0473 (4)
H18B	0.3227	0.7656	0.6433	0.057*
H18A	0.4110	0.6414	0.6170	0.057*
C19	0.1752 (2)	0.6252 (2)	0.56735 (18)	0.0589 (5)
H19B	0.1787	0.5667	0.5027	0.071*
H19A	0.1577	0.5806	0.6183	0.071*
C20	0.0358 (2)	0.7076 (2)	0.56372 (19)	0.0656 (6)
H20A	0.0282	0.7624	0.6299	0.079*
H20B	−0.0624	0.6585	0.5492	0.079*
C21	0.0472 (2)	0.7822 (2)	0.48615 (18)	0.0639 (6)
H21B	−0.0502	0.8283	0.4865	0.077*
H21A	0.0515	0.7271	0.4199	0.077*
C22	0.1902 (2)	0.86958 (18)	0.50166 (17)	0.0547 (5)
H22B	0.1666	0.9322	0.4662	0.066*
H22A	0.2040	0.9088	0.5730	0.066*
C23	0.3450 (2)	0.81263 (15)	0.46655 (13)	0.0376 (4)
C24	0.5760 (2)	0.80974 (19)	0.36486 (16)	0.0527 (5)
H24B	0.6604	0.8544	0.4105	0.063*
H24A	0.5910	0.8221	0.2980	0.063*
C25	0.5840 (2)	0.67836 (19)	0.36216 (15)	0.0529 (5)
H25B	0.6914	0.6500	0.3460	0.063*
H25A	0.5091	0.6329	0.3098	0.063*
C26	0.5433 (2)	0.65656 (16)	0.46223 (14)	0.0429 (4)
H26B	0.5223	0.5704	0.4545	0.051*
H26A	0.6347	0.6805	0.5097	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0346 (2)	0.0303 (2)	0.0314 (2)	0.00208 (15)	0.00147 (16)	0.01090 (16)
S2	0.0605 (3)	0.0321 (2)	0.0387 (3)	0.0009 (2)	−0.0147 (2)	0.01085 (18)
O1	0.0424 (6)	0.0452 (7)	0.0508 (7)	−0.0001 (5)	0.0073 (6)	0.0248 (6)
O2	0.0575 (7)	0.0361 (6)	0.0312 (6)	0.0053 (5)	−0.0030 (5)	0.0065 (5)
N1	0.0487 (8)	0.0268 (7)	0.0335 (8)	0.0009 (6)	−0.0098 (7)	0.0083 (6)
N2	0.0681 (11)	0.0335 (8)	0.0479 (9)	−0.0050 (7)	−0.0077 (8)	0.0076 (7)
N3	0.0370 (7)	0.0378 (8)	0.0365 (8)	0.0020 (6)	−0.0005 (6)	0.0143 (6)
N4	0.0464 (9)	0.0440 (9)	0.0553 (10)	0.0043 (7)	0.0041 (7)	0.0271 (8)
C1	0.0332 (8)	0.0278 (8)	0.0323 (8)	0.0011 (6)	−0.0026 (6)	0.0093 (7)
C2	0.0283 (7)	0.0293 (8)	0.0338 (8)	0.0014 (6)	0.0003 (6)	0.0085 (7)
C3	0.0404 (9)	0.0257 (8)	0.0303 (8)	−0.0013 (6)	−0.0055 (7)	0.0073 (6)
C4	0.0399 (9)	0.0380 (9)	0.0353 (9)	0.0024 (7)	−0.0031 (7)	0.0067 (7)
C5	0.0583 (12)	0.0405 (10)	0.0526 (12)	0.0158 (9)	−0.0086 (9)	0.0014 (9)
C6	0.0874 (16)	0.0262 (9)	0.0608 (13)	−0.0007 (10)	−0.0164 (12)	0.0114 (9)
C7	0.0717 (13)	0.0409 (10)	0.0488 (11)	−0.0194 (10)	−0.0084 (10)	0.0174 (9)
C8	0.0444 (9)	0.0403 (9)	0.0327 (9)	−0.0070 (7)	−0.0024 (7)	0.0086 (7)
C9	0.0500 (11)	0.0808 (15)	0.0576 (13)	−0.0012 (11)	0.0125 (10)	0.0184 (12)
C10	0.0486 (11)	0.0661 (13)	0.0597 (13)	−0.0044 (10)	0.0123 (10)	0.0107 (11)
C11	0.0370 (8)	0.0302 (9)	0.0356 (9)	0.0019 (7)	−0.0024 (7)	0.0122 (7)
C12	0.0326 (8)	0.0403 (9)	0.0295 (8)	0.0017 (7)	−0.0024 (6)	0.0080 (7)
C13	0.0432 (10)	0.0556 (11)	0.0466 (11)	−0.0027 (8)	0.0015 (8)	0.0199 (9)
C14	0.0379 (10)	0.0952 (18)	0.0475 (11)	−0.0059 (11)	0.0051 (9)	0.0184 (11)
C15	0.0423 (11)	0.0912 (18)	0.0594 (14)	0.0203 (12)	0.0024 (10)	0.0045 (12)
C16	0.0546 (12)	0.0571 (13)	0.0788 (16)	0.0213 (10)	−0.0019 (11)	0.0063 (12)
C17	0.0441 (10)	0.0400 (10)	0.0564 (12)	0.0035 (8)	−0.0029 (9)	0.0103 (9)
C18	0.0533 (11)	0.0528 (11)	0.0413 (10)	0.0029 (9)	0.0040 (8)	0.0220 (9)
C19	0.0607 (12)	0.0579 (13)	0.0649 (13)	−0.0064 (10)	0.0129 (10)	0.0266 (11)
C20	0.0470 (11)	0.0824 (16)	0.0721 (15)	−0.0043 (11)	0.0142 (11)	0.0263 (13)
C21	0.0391 (10)	0.0882 (16)	0.0709 (15)	0.0131 (10)	0.0090 (10)	0.0305 (13)
C22	0.0573 (12)	0.0495 (11)	0.0635 (13)	0.0199 (9)	0.0147 (10)	0.0232 (10)
C23	0.0400 (9)	0.0339 (9)	0.0399 (9)	0.0001 (7)	−0.0008 (7)	0.0113 (7)
C24	0.0401 (10)	0.0677 (13)	0.0576 (12)	0.0005 (9)	0.0076 (9)	0.0284 (11)
C25	0.0489 (11)	0.0609 (12)	0.0489 (11)	0.0122 (9)	0.0076 (9)	0.0121 (10)
C26	0.0446 (10)	0.0385 (9)	0.0465 (10)	0.0094 (8)	0.0007 (8)	0.0122 (8)

S1—O1	1.4285 (12)	C12—C17	1.371 (2)
S1—O2	1.4413 (13)	C12—C13	1.373 (2)
S1—C1	1.7291 (16)	C13—C14	1.383 (3)
S1—C12	1.7697 (16)	C13—H13	0.9300
S2—C2	1.7037 (16)	C14—C15	1.366 (3)
N1—C2	1.334 (2)	C14—H14	0.9300
N1—C3	1.424 (2)	C15—C16	1.358 (3)
N1—H1N	0.86 (2)	C15—H15	0.9300
N2—C11	1.143 (2)	C16—C17	1.387 (3)
N3—C23	1.308 (2)	C16—H16	0.9300
N3—C26	1.465 (2)	C17—H17	0.9300
N3—C18	1.469 (2)	C18—C19	1.509 (3)
N4—C23	1.305 (2)	C18—H18B	0.9700
N4—C24	1.450 (2)	C18—H18A	0.9700
N4—H4N	0.82 (2)	C19—C20	1.505 (3)
C1—C11	1.408 (2)	C19—H19B	0.9700
C1—C2	1.411 (2)	C19—H19A	0.9700
C3—C8	1.377 (2)	C20—C21	1.514 (3)
C3—C4	1.393 (2)	C20—H20A	0.9700
C4—C5	1.381 (3)	C20—H20B	0.9700
C4—C10	1.491 (3)	C21—C22	1.515 (3)
C5—C6	1.361 (3)	C21—H21B	0.9700
C5—H5	0.9300	C21—H21A	0.9700
C6—C7	1.358 (3)	C22—C23	1.494 (2)
C6—H6	0.9300	C22—H22B	0.9700
C7—C8	1.383 (3)	C22—H22A	0.9700
C7—H7	0.9300	C24—C25	1.485 (3)
C8—C9	1.500 (3)	C24—H24B	0.9700
C9—H9C	0.9600	C24—H24A	0.9700
C9—H9B	0.9600	C25—C26	1.499 (3)
C9—H9A	0.9600	C25—H25B	0.9700
C10—H10C	0.9600	C25—H25A	0.9700
C10—H10B	0.9600	C26—H26B	0.9700
C10—H10A	0.9600	C26—H26A	0.9700
O1—S1—O2	117.84 (8)	C16—C15—C14	120.04 (19)
O1—S1—C1	109.46 (8)	C16—C15—H15	120.0
O2—S1—C1	108.65 (7)	C14—C15—H15	120.0
O1—S1—C12	107.00 (8)	C15—C16—C17	120.9 (2)
O2—S1—C12	106.90 (8)	C15—C16—H16	119.5
C1—S1—C12	106.39 (8)	C17—C16—H16	119.5
C2—N1—C3	125.95 (14)	C12—C17—C16	118.62 (19)
C2—N1—H1N	116.6 (13)	C12—C17—H17	120.7
C3—N1—H1N	116.7 (13)	C16—C17—H17	120.7
C23—N3—C26	122.01 (14)	N3—C18—C19	113.53 (16)
C23—N3—C18	121.92 (15)	N3—C18—H18B	108.9
C26—N3—C18	115.99 (14)	C19—C18—H18B	108.9
C23—N4—C24	122.62 (16)	N3—C18—H18A	108.9
C23—N4—H4N	118.0 (15)	C19—C18—H18A	108.9
C24—N4—H4N	119.4 (15)	H18B—C18—H18A	107.7
C11—C1—C2	120.44 (14)	C20—C19—C18	113.49 (18)
C11—C1—S1	113.16 (11)	C20—C19—H19B	108.9
C2—C1—S1	126.38 (12)	C18—C19—H19B	108.9
N1—C2—C1	120.26 (14)	C20—C19—H19A	108.9
N1—C2—S2	120.37 (12)	C18—C19—H19A	108.9
C1—C2—S2	119.37 (12)	H19B—C19—H19A	107.7
C8—C3—C4	122.55 (15)	C19—C20—C21	114.37 (18)
C8—C3—N1	118.90 (15)	C19—C20—H20A	108.7
C4—C3—N1	118.28 (15)	C21—C20—H20A	108.7
C5—C4—C3	117.24 (17)	C19—C20—H20B	108.7
C5—C4—C10	121.19 (18)	C21—C20—H20B	108.7
C3—C4—C10	121.56 (16)	H20A—C20—H20B	107.6
C6—C5—C4	120.93 (19)	C20—C21—C22	115.35 (19)
C6—C5—H5	119.5	C20—C21—H21B	108.4
C4—C5—H5	119.5	C22—C21—H21B	108.4
C7—C6—C5	120.74 (18)	C20—C21—H21A	108.4
C7—C6—H6	119.6	C22—C21—H21A	108.4
C5—C6—H6	119.6	H21B—C21—H21A	107.5
C6—C7—C8	121.06 (19)	C23—C22—C21	114.77 (17)
C6—C7—H7	119.5	C23—C22—H22B	108.6
C8—C7—H7	119.5	C21—C22—H22B	108.6
C3—C8—C7	117.46 (17)	C23—C22—H22A	108.6
C3—C8—C9	121.48 (17)	C21—C22—H22A	108.6
C7—C8—C9	121.06 (18)	H22B—C22—H22A	107.6
C8—C9—H9C	109.5	N4—C23—N3	121.38 (16)
C8—C9—H9B	109.5	N4—C23—C22	118.27 (16)
H9C—C9—H9B	109.5	N3—C23—C22	120.34 (16)
C8—C9—H9A	109.5	N4—C24—C25	108.70 (16)
H9C—C9—H9A	109.5	N4—C24—H24B	110.0
H9B—C9—H9A	109.5	C25—C24—H24B	110.0
C4—C10—H10C	109.5	N4—C24—H24A	110.0
C4—C10—H10B	109.5	C25—C24—H24A	110.0
H10C—C10—H10B	109.5	H24B—C24—H24A	108.3
C4—C10—H10A	109.5	C24—C25—C26	110.45 (17)
H10C—C10—H10A	109.5	C24—C25—H25B	109.6
H10B—C10—H10A	109.5	C26—C25—H25B	109.6
N2—C11—C1	176.46 (17)	C24—C25—H25A	109.6
C17—C12—C13	120.95 (17)	C26—C25—H25A	109.6
C17—C12—S1	119.06 (13)	H25B—C25—H25A	108.1
C13—C12—S1	119.98 (14)	N3—C26—C25	112.07 (14)
C12—C13—C14	119.24 (19)	N3—C26—H26B	109.2
C12—C13—H13	120.4	C25—C26—H26B	109.2
C14—C13—H13	120.4	N3—C26—H26A	109.2
C15—C14—C13	120.2 (2)	C25—C26—H26A	109.2
C15—C14—H14	119.9	H26B—C26—H26A	107.9
C13—C14—H14	119.9
O1—S1—C1—C11	42.43 (14)	O1—S1—C12—C13	174.72 (14)
O2—S1—C1—C11	172.37 (11)	O2—S1—C12—C13	47.62 (16)
C12—S1—C1—C11	−72.86 (13)	C1—S1—C12—C13	−68.34 (16)
O1—S1—C1—C2	−139.31 (14)	C17—C12—C13—C14	−1.0 (3)
O2—S1—C1—C2	−9.36 (17)	S1—C12—C13—C14	−179.96 (14)
C12—S1—C1—C2	105.41 (15)	C12—C13—C14—C15	0.8 (3)
C3—N1—C2—C1	171.24 (15)	C13—C14—C15—C16	−0.4 (3)
C3—N1—C2—S2	−8.4 (2)	C14—C15—C16—C17	0.1 (4)
C11—C1—C2—N1	176.19 (14)	C13—C12—C17—C16	0.8 (3)
S1—C1—C2—N1	−2.0 (2)	S1—C12—C17—C16	179.74 (15)
C11—C1—C2—S2	−4.2 (2)	C15—C16—C17—C12	−0.3 (3)
S1—C1—C2—S2	177.69 (9)	C23—N3—C18—C19	74.2 (2)
C2—N1—C3—C8	101.1 (2)	C26—N3—C18—C19	−109.05 (18)
C2—N1—C3—C4	−84.8 (2)	N3—C18—C19—C20	−80.1 (2)
C8—C3—C4—C5	0.6 (2)	C18—C19—C20—C21	59.1 (3)
N1—C3—C4—C5	−173.36 (15)	C19—C20—C21—C22	−61.7 (3)
C8—C3—C4—C10	−178.51 (17)	C20—C21—C22—C23	79.5 (2)
N1—C3—C4—C10	7.6 (2)	C24—N4—C23—N3	−4.3 (3)
C3—C4—C5—C6	−0.4 (3)	C24—N4—C23—C22	175.81 (18)
C10—C4—C5—C6	178.72 (19)	C26—N3—C23—N4	−7.3 (3)
C4—C5—C6—C7	−0.6 (3)	C18—N3—C23—N4	169.31 (17)
C5—C6—C7—C8	1.4 (3)	C26—N3—C23—C22	172.61 (16)
C4—C3—C8—C7	0.2 (2)	C18—N3—C23—C22	−10.8 (3)
N1—C3—C8—C7	174.06 (16)	C21—C22—C23—N4	122.0 (2)
C4—C3—C8—C9	179.79 (17)	C21—C22—C23—N3	−57.8 (3)
N1—C3—C8—C9	−6.3 (2)	C23—N4—C24—C25	35.4 (3)
C6—C7—C8—C3	−1.2 (3)	N4—C24—C25—C26	−53.5 (2)
C6—C7—C8—C9	179.24 (18)	C23—N3—C26—C25	−14.2 (2)
O1—S1—C12—C17	−4.27 (16)	C18—N3—C26—C25	169.07 (16)
O2—S1—C12—C17	−131.37 (14)	C24—C25—C26—N3	44.5 (2)
C1—S1—C12—C17	112.67 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86 (2)	1.98 (2)	2.7091 (19)	143 (2)
N4—H4N···S2i	0.82 (2)	2.45 (2)	3.2335 (19)	161 (2)

Table 1

Selected bond lengths (Å)

S1—O1	1.4285 (12)
S1—O2	1.4413 (13)
S1—C1	1.7291 (16)
S2—C2	1.7037 (16)
N3—C23	1.308 (2)
N4—C23	1.305 (2)
C1—C2	1.411 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86 (2)	1.98 (2)	2.7091 (19)	143 (2)
N4—H4N⋯S2i	0.82 (2)	2.45 (2)	3.2335 (19)	161 (2)

Symmetry code: (i) .