N,N′-Bis[(1H-imidazol-1-yl)meth­yl]-2,2′-(disulfanedi­yl)dianiline

Lee, H.M.; Hsieh, C.-C.; Horng, Y.-C.

doi:10.1107/S1600536812025330

organic compounds

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Volume 68| Part 7| July 2012| Page o2051

https://doi.org/10.1107/S1600536812025330

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N,N′-Bis[(1H-imidazol-1-yl)methyl]-2,2′-(disulfanediyl)dianiline

Hon Man Lee,^a Chang-Chih Hsieh ^a and Yih-Chern Horng ^a ^*

^aNational Changhua University of Education, Department of Chemistry, Changhua, Taiwan 50058
^*Correspondence e-mail: ychorng@cc.ncue.edu.tw

(Received 1 June 2012; accepted 4 June 2012; online 13 June 2012)

The symmetrical title compound, C₂₀H₂₀N₆S₂, contains a disulfide bond of 2.0884 (6) Å. The C—S—S—C torsion angle is −59.57 (7)°. In the crystal, classical N—H⋯N and non-classical C—H⋯N hydrogen bonds link the compounds into chains along the a axis.

Related literature

For transition metal complexes having related ligands, see: Hsieh et al. (2009a ,b ).

Experimental

Crystal data

C₂₀H₂₀N₆S₂
M_r = 408.56
Monoclinic, P 2₁ /c
a = 11.2009 (10) Å
b = 11.6067 (10) Å
c = 15.5230 (14) Å
β = 97.162 (2)°
V = 2002.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 150 K
0.38 × 0.32 × 0.24 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.888, T_max = 0.954
23330 measured reflections
4970 independent reflections
3844 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.128
S = 0.96
4970 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H22⋯N4ⁱ	0.818 (17)	2.252 (17)	2.9825 (19)	148.9 (15)
C1—H1⋯N2ⁱⁱ	0.93	2.58	3.448 (2)	155
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: DIAMOND (Brandenburg, 2006 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025330/wn2478sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025330/wn2478Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025330/wn2478Isup3.cml

checkCIF report

Comment top

In our research, we have focused on the synthesis of low-molecular-weight complexes, which exhibited the structural and functional features of the active sites in particular enzymes, such as Ni-containing methyl coenzyme M reductase (Hsieh et al., 2009b) and Fe-containing nitrile hydratase (Hsieh et al., 2009a). The synthesis and crystal structure determination of the title compound are reported here. This compound will be used as a coordination ligand in related studies.

The disulfide bond length is 2.0884 (6) Å and the C—S—S—C torsion angle is 59.56 (7)° (Fig. 1). In the crystal structure the compound does not exhibit crystallographic symmetry. Classical N—H···N and non-classical C—H···N hydrogen bonds (Table 1) link the compounds into one-dimensional chains along the a-axis (Fig. 2).

Related literature top

For transition metal complexes having related ligands, see: Hsieh et al. (2009a,b).

Experimental top

Pyrazole (1.0 g, 14.7 mmol) was dissolved in 50 ml CH₂Cl₂ and treated with formaldehyde (37%, 1.19 g, 14.7 mmol). After stirring at room temperature for 10 min, the mixture was added to a batch of 2-aminophenyl disulfide (1.82 g, 7.32 mmol) and stirred for a further 12 h. After completion of the reaction, the solution was extracted with distilled water. Portions of the CH₂Cl₂ extract were collected and dried using anhydrous MgSO₄. The solvent was then removed under vacuum to afford a yellow powder (2.56 g, 86%). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a tetrahydrofuran solution of the compound at -4 °C.

Structure description top

For transition metal complexes having related ligands, see: Hsieh et al. (2009a,b).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: DIAMOND (Brandenburg, 2006).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids for the non-hydrogen atoms. The H atoms are depicted as spheres of arbitrary radius.
	Fig. 2. A view of the one-dimensional hydrogen-bonded chain, showing the hydrogen bonds as dashed lines.

N,N'-Bis[(1H-imidazol-1-yl)methyl]-2,2'- (disulfanediyl)dianiline top

Crystal data top

C₂₀H₂₀N₆S₂	F(000) = 840
M_r = 408.56	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2009 (10) Å	Cell parameters from 6226 reflections
b = 11.6067 (10) Å	θ = 2.2–27.2°
c = 15.5230 (14) Å	µ = 0.28 mm⁻¹
β = 97.162 (2)°	T = 150 K
V = 2002.3 (3) Å³	Block, yellow
Z = 4	0.38 × 0.32 × 0.24 mm

Data collection top

Bruker SMART APEXII diffractometer	4970 independent reflections
Radiation source: fine-focus sealed tube	3844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
T_min = 0.888, T_max = 0.954	k = −15→15
23330 measured reflections	l = −20→20

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.1P)² + 0.0208P] where P = (F_o² + 2F_c²)/3
4970 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₂₀N₆S₂	V = 2002.3 (3) Å³
M_r = 408.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2009 (10) Å	µ = 0.28 mm⁻¹
b = 11.6067 (10) Å	T = 150 K
c = 15.5230 (14) Å	0.38 × 0.32 × 0.24 mm
β = 97.162 (2)°

Data collection top

Bruker SMART APEXII diffractometer	4970 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3844 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.954	R_int = 0.026
23330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.27 e Å⁻³
4970 reflections	Δρ_min = −0.26 e Å⁻³
261 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	−0.02094 (3)	0.08013 (3)	0.76606 (3)	0.03264 (13)
S2	0.01131 (3)	0.25438 (3)	0.79328 (3)	0.03404 (13)
N3	0.20015 (10)	0.01306 (11)	1.07381 (8)	0.0302 (3)
N1	0.36181 (11)	−0.17778 (11)	0.86130 (8)	0.0317 (3)
N4	0.14835 (12)	−0.08760 (11)	1.04385 (10)	0.0390 (3)
N2	0.47440 (12)	−0.20760 (14)	0.84774 (10)	0.0460 (4)
N6	0.10991 (11)	0.15689 (12)	0.97273 (8)	0.0338 (3)
N5	0.21637 (11)	−0.02980 (11)	0.82527 (8)	0.0312 (3)
C7	0.33157 (12)	−0.05670 (13)	0.87099 (10)	0.0309 (3)
H7A	0.3316	−0.0392	0.9321	0.037*
H7B	0.3923	−0.0091	0.8491	0.037*
C8	0.13251 (13)	0.12062 (13)	1.06103 (10)	0.0321 (3)
H8A	0.0561	0.1112	1.0836	0.039*
H8B	0.1768	0.1808	1.0946	0.039*
C1	0.30946 (13)	−0.00488 (16)	1.12009 (10)	0.0384 (4)
H1	0.3605	0.0512	1.1469	0.046*
C3	0.22890 (16)	−0.16789 (15)	1.07264 (12)	0.0446 (4)
H3	0.2182	−0.2463	1.0622	0.053*
C2	0.33048 (15)	−0.12061 (16)	1.12002 (11)	0.0455 (4)
H2	0.3982	−0.1594	1.1461	0.055*
C4	0.29052 (19)	−0.26996 (15)	0.86760 (14)	0.0490 (4)
H4	0.2098	−0.2687	0.8762	0.059*
C5	0.3583 (2)	−0.36500 (17)	0.85913 (13)	0.0607 (6)
H5	0.3348	−0.4417	0.8613	0.073*
C6	0.4712 (2)	−0.32236 (18)	0.84645 (13)	0.0595 (6)
H6	0.5365	−0.3686	0.8381	0.071*
C13	0.16083 (13)	0.25746 (12)	0.84587 (10)	0.0288 (3)
C15	0.19876 (12)	−0.00747 (12)	0.73713 (9)	0.0277 (3)
C14	0.19334 (12)	0.21299 (12)	0.93032 (9)	0.0271 (3)
C16	0.09108 (13)	0.04528 (12)	0.69947 (10)	0.0304 (3)
C9	0.31319 (13)	0.22646 (13)	0.96785 (10)	0.0317 (3)
H9	0.3368	0.1982	1.0234	0.038*
C10	0.39688 (14)	0.28116 (14)	0.92343 (11)	0.0372 (4)
H10	0.4754	0.2902	0.9500	0.045*
C11	0.36564 (16)	0.32242 (15)	0.84051 (12)	0.0429 (4)
H11	0.4225	0.3578	0.8105	0.052*
C20	0.28490 (14)	−0.03762 (13)	0.68293 (10)	0.0342 (3)
H20	0.3558	−0.0736	0.7063	0.041*
C17	0.07364 (16)	0.06746 (13)	0.61034 (11)	0.0389 (4)
H17	0.0026	0.1023	0.5859	0.047*
C18	0.15999 (17)	0.03861 (14)	0.55792 (11)	0.0433 (4)
H18	0.1478	0.0544	0.4987	0.052*
C19	0.26499 (16)	−0.01419 (14)	0.59480 (11)	0.0415 (4)
H19	0.3232	−0.0343	0.5597	0.050*
C12	0.24702 (15)	0.31009 (14)	0.80253 (10)	0.0382 (4)
H12	0.2251	0.3379	0.7466	0.046*
H22	0.0410 (15)	0.1489 (14)	0.9491 (11)	0.029 (4)*
H21	0.1641 (15)	−0.0085 (15)	0.8556 (11)	0.036 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02746 (19)	0.0298 (2)	0.0386 (2)	0.00133 (13)	−0.00418 (14)	0.00020 (15)
S2	0.0400 (2)	0.0265 (2)	0.0330 (2)	0.00832 (14)	−0.00588 (16)	0.00215 (14)
N3	0.0269 (6)	0.0364 (7)	0.0274 (6)	0.0039 (5)	0.0033 (5)	0.0034 (5)
N1	0.0289 (6)	0.0306 (7)	0.0343 (7)	0.0044 (5)	−0.0016 (5)	−0.0033 (5)
N4	0.0324 (7)	0.0366 (7)	0.0478 (8)	0.0018 (5)	0.0038 (6)	0.0016 (6)
N2	0.0330 (7)	0.0521 (9)	0.0504 (9)	0.0144 (6)	−0.0048 (6)	−0.0143 (7)
N6	0.0277 (6)	0.0436 (8)	0.0283 (7)	−0.0016 (5)	−0.0029 (5)	0.0089 (5)
N5	0.0277 (6)	0.0371 (7)	0.0282 (6)	0.0087 (5)	0.0018 (5)	0.0003 (5)
C7	0.0282 (7)	0.0285 (7)	0.0346 (8)	0.0019 (5)	−0.0018 (6)	−0.0058 (6)
C8	0.0311 (7)	0.0373 (8)	0.0278 (7)	0.0064 (6)	0.0034 (6)	0.0037 (6)
C1	0.0323 (7)	0.0538 (10)	0.0279 (8)	0.0103 (7)	−0.0009 (6)	0.0002 (7)
C3	0.0440 (9)	0.0375 (9)	0.0533 (11)	0.0108 (7)	0.0104 (8)	0.0060 (8)
C2	0.0422 (9)	0.0565 (11)	0.0370 (9)	0.0210 (8)	0.0023 (7)	0.0054 (8)
C4	0.0564 (11)	0.0355 (9)	0.0553 (12)	−0.0075 (8)	0.0083 (9)	−0.0083 (8)
C5	0.0962 (17)	0.0302 (9)	0.0521 (12)	0.0047 (10)	−0.0055 (11)	−0.0059 (8)
C6	0.0685 (13)	0.0504 (11)	0.0531 (11)	0.0337 (10)	−0.0175 (10)	−0.0168 (9)
C13	0.0360 (7)	0.0219 (7)	0.0275 (7)	0.0029 (5)	0.0001 (6)	−0.0020 (5)
C15	0.0316 (7)	0.0211 (7)	0.0296 (7)	−0.0043 (5)	0.0005 (5)	−0.0017 (5)
C14	0.0308 (7)	0.0230 (7)	0.0272 (7)	0.0027 (5)	0.0025 (5)	−0.0017 (5)
C16	0.0340 (7)	0.0235 (7)	0.0318 (8)	−0.0052 (5)	−0.0033 (6)	−0.0024 (6)
C9	0.0328 (7)	0.0318 (8)	0.0295 (8)	0.0011 (6)	0.0006 (6)	−0.0012 (6)
C10	0.0331 (8)	0.0364 (8)	0.0422 (9)	−0.0037 (6)	0.0050 (6)	−0.0063 (7)
C11	0.0450 (9)	0.0420 (10)	0.0435 (10)	−0.0103 (7)	0.0125 (7)	0.0004 (7)
C20	0.0358 (7)	0.0285 (8)	0.0385 (9)	−0.0057 (6)	0.0057 (6)	−0.0043 (6)
C17	0.0489 (9)	0.0294 (8)	0.0349 (9)	−0.0063 (7)	−0.0089 (7)	0.0011 (6)
C18	0.0642 (11)	0.0355 (9)	0.0290 (8)	−0.0150 (8)	0.0010 (7)	−0.0001 (7)
C19	0.0542 (10)	0.0348 (8)	0.0378 (9)	−0.0143 (7)	0.0146 (7)	−0.0071 (7)
C12	0.0510 (9)	0.0346 (8)	0.0289 (8)	−0.0041 (7)	0.0051 (7)	0.0033 (6)

Geometric parameters (Å, º) top

S1—C16	1.7691 (16)	C4—C5	1.355 (3)
S1—S2	2.0884 (6)	C4—H4	0.9300
S2—C13	1.7697 (15)	C5—C6	1.394 (3)
N3—C1	1.3562 (18)	C5—H5	0.9300
N3—N4	1.3605 (18)	C6—H6	0.9300
N3—C8	1.4609 (18)	C13—C12	1.385 (2)
N1—C4	1.346 (2)	C13—C14	1.414 (2)
N1—N2	1.3493 (18)	C15—C20	1.401 (2)
N1—C7	1.4577 (19)	C15—C16	1.4127 (19)
N4—C3	1.335 (2)	C14—C9	1.4039 (19)
N2—C6	1.333 (3)	C16—C17	1.397 (2)
N6—C14	1.3727 (19)	C9—C10	1.385 (2)
N6—C8	1.4260 (19)	C9—H9	0.9300
N6—H22	0.818 (17)	C10—C11	1.377 (3)
N5—C15	1.3823 (18)	C10—H10	0.9300
N5—C7	1.4276 (17)	C11—C12	1.392 (2)
N5—H21	0.833 (17)	C11—H11	0.9300
C7—H7A	0.9700	C20—C19	1.385 (2)
C7—H7B	0.9700	C20—H20	0.9300
C8—H8A	0.9700	C17—C18	1.381 (3)
C8—H8B	0.9700	C17—H17	0.9300
C1—C2	1.364 (2)	C18—C19	1.385 (3)
C1—H1	0.9300	C18—H18	0.9300
C3—C2	1.389 (3)	C19—H19	0.9300
C3—H3	0.9300	C12—H12	0.9300
C2—H2	0.9300

C16—S1—S2	102.84 (5)	C4—C5—H5	127.6
C13—S2—S1	104.05 (5)	C6—C5—H5	127.6
C1—N3—N4	111.56 (13)	N2—C6—C5	112.10 (16)
C1—N3—C8	128.45 (14)	N2—C6—H6	123.9
N4—N3—C8	119.71 (12)	C5—C6—H6	123.9
C4—N1—N2	112.46 (15)	C12—C13—C14	119.78 (14)
C4—N1—C7	127.68 (14)	C12—C13—S2	117.49 (12)
N2—N1—C7	119.81 (13)	C14—C13—S2	122.68 (11)
C3—N4—N3	104.09 (14)	N5—C15—C20	121.57 (13)
C6—N2—N1	103.56 (15)	N5—C15—C16	120.00 (13)
C14—N6—C8	123.45 (13)	C20—C15—C16	118.43 (14)
C14—N6—H22	120.0 (11)	N6—C14—C9	121.79 (13)
C8—N6—H22	116.2 (11)	N6—C14—C13	120.39 (13)
C15—N5—C7	122.80 (13)	C9—C14—C13	117.81 (13)
C15—N5—H21	118.7 (12)	C17—C16—C15	119.77 (14)
C7—N5—H21	116.1 (12)	C17—C16—S1	120.99 (12)
N5—C7—N1	111.52 (12)	C15—C16—S1	119.24 (11)
N5—C7—H7A	109.3	C10—C9—C14	121.06 (14)
N1—C7—H7A	109.3	C10—C9—H9	119.5
N5—C7—H7B	109.3	C14—C9—H9	119.5
N1—C7—H7B	109.3	C11—C10—C9	121.06 (15)
H7A—C7—H7B	108.0	C11—C10—H10	119.5
N6—C8—N3	114.18 (12)	C9—C10—H10	119.5
N6—C8—H8A	108.7	C10—C11—C12	118.55 (15)
N3—C8—H8A	108.7	C10—C11—H11	120.7
N6—C8—H8B	108.7	C12—C11—H11	120.7
N3—C8—H8B	108.7	C19—C20—C15	120.38 (15)
H8A—C8—H8B	107.6	C19—C20—H20	119.8
N3—C1—C2	107.18 (15)	C15—C20—H20	119.8
N3—C1—H1	126.4	C18—C17—C16	121.16 (16)
C2—C1—H1	126.4	C18—C17—H17	119.4
N4—C3—C2	112.12 (16)	C16—C17—H17	119.4
N4—C3—H3	123.9	C17—C18—C19	119.00 (15)
C2—C3—H3	123.9	C17—C18—H18	120.5
C1—C2—C3	105.04 (14)	C19—C18—H18	120.5
C1—C2—H2	127.5	C18—C19—C20	121.26 (16)
C3—C2—H2	127.5	C18—C19—H19	119.4
N1—C4—C5	107.17 (19)	C20—C19—H19	119.4
N1—C4—H4	126.4	C13—C12—C11	121.72 (15)
C5—C4—H4	126.4	C13—C12—H12	119.1
C4—C5—C6	104.70 (18)	C11—C12—H12	119.1

C16—S1—S2—C13	−59.57 (8)	C8—N6—C14—C13	−173.15 (14)
C1—N3—N4—C3	−0.24 (18)	C12—C13—C14—N6	−177.59 (14)
C8—N3—N4—C3	−174.71 (13)	S2—C13—C14—N6	5.04 (19)
C4—N1—N2—C6	−0.47 (19)	C12—C13—C14—C9	1.3 (2)
C7—N1—N2—C6	177.01 (14)	S2—C13—C14—C9	−176.10 (10)
C15—N5—C7—N1	−81.64 (17)	N5—C15—C16—C17	−179.88 (13)
C4—N1—C7—N5	−44.9 (2)	C20—C15—C16—C17	−0.9 (2)
N2—N1—C7—N5	138.08 (14)	N5—C15—C16—S1	−0.91 (19)
C14—N6—C8—N3	−80.33 (18)	C20—C15—C16—S1	178.09 (10)
C1—N3—C8—N6	118.43 (16)	S2—S1—C16—C17	−83.60 (12)
N4—N3—C8—N6	−68.13 (18)	S2—S1—C16—C15	97.44 (11)
N4—N3—C1—C2	0.44 (18)	N6—C14—C9—C10	178.62 (14)
C8—N3—C1—C2	174.31 (14)	C13—C14—C9—C10	−0.2 (2)
N3—N4—C3—C2	−0.06 (19)	C14—C9—C10—C11	−1.1 (2)
N3—C1—C2—C3	−0.44 (18)	C9—C10—C11—C12	1.3 (2)
N4—C3—C2—C1	0.3 (2)	N5—C15—C20—C19	−179.97 (14)
N2—N1—C4—C5	0.8 (2)	C16—C15—C20—C19	1.0 (2)
C7—N1—C4—C5	−176.40 (15)	C15—C16—C17—C18	0.1 (2)
N1—C4—C5—C6	−0.8 (2)	S1—C16—C17—C18	−178.89 (12)
N1—N2—C6—C5	−0.1 (2)	C16—C17—C18—C19	0.6 (2)
C4—C5—C6—N2	0.6 (2)	C17—C18—C19—C20	−0.4 (2)
S1—S2—C13—C12	112.56 (11)	C15—C20—C19—C18	−0.4 (2)
S1—S2—C13—C14	−70.02 (12)	C14—C13—C12—C11	−1.1 (2)
C7—N5—C15—C20	16.4 (2)	S2—C13—C12—C11	176.41 (13)
C7—N5—C15—C16	−164.62 (13)	C10—C11—C12—C13	−0.2 (3)
C8—N6—C14—C9	8.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H22···N4ⁱ	0.818 (17)	2.252 (17)	2.9825 (19)	148.9 (15)
C1—H1···N2ⁱⁱ	0.93	2.58	3.448 (2)	155

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₆S₂
M_r	408.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	11.2009 (10), 11.6067 (10), 15.5230 (14)
β (°)	97.162 (2)
V (Å³)	2002.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.38 × 0.32 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.888, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	23330, 4970, 3844
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.128, 0.96
No. of reflections	4970
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H22···N4ⁱ	0.818 (17)	2.252 (17)	2.9825 (19)	148.9 (15)
C1—H1···N2ⁱⁱ	0.93	2.58	3.448 (2)	155

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y, −z+2.

Acknowledgements

We thank the National Science Council of Taiwan for financial support of this work.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Hsieh, C.-C., Chao, W.-J., Horng, Y.-C. & Lee, H. M. (2009b). J. Chin. Chem. Soc. 56, 435–442. CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar