3,3′-Dibenzoyl-1,1′-(3,6-dioxaoctane-1,8-di­yl)dithio­urea

Sow, M.M.; Diouf, O.; Barry, A.H.; Gaye, M.; Sall, A.S.

doi:10.1107/S1600536809005662

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o569

doi:10.1107/S1600536809005662

Open

access

3,3′-Dibenzoyl-1,1′-(3,6-dioxaoctane-1,8-diyl)dithiourea

Mouhamadou Moustapha Sow,^a Ousmane Diouf,^a Aliou Hamady Barry,^b Mohamed Gaye ^a ^* and Abdou Salam Sall ^a

^aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDépartement de Chimie, Faculté des Sciences, Université de Nouakchott, Nouakchott, Mauritania
^*Correspondence e-mail: mlgayeastou@yahoo.fr

(Received 15 January 2009; accepted 17 February 2009; online 21 February 2009)

In the molecule of the title compound, C₂₂H₂₆N₄O₄S₂, the central O—CH₂—CH₂—O chain adopts a synclinal conformation [torsion angle = 65.0 (2)°]. The crystal structure is stabilized by intramolecular N—H⋯O=C and intermolecular N—H⋯O—C hydrogen bonds.

Related literature

For related structures, see: Avşar et al. (2003 ); Arslan et al. (2004 ); Du & Du (2008 ); Ding et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₆N₄O₄S₂
M_r = 474.59
Triclinic, $[P \overline 1]$
a = 7.9718 (2) Å
b = 9.2177 (3) Å
c = 16.4106 (5) Å
α = 81.018 (2)°
β = 83.364 (2)°
γ = 80.450 (2)°
V = 1169.60 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.10 mm

Data collection

Nonius Kappa CCD diffractometer
Absorption correction: none
7989 measured reflections
4211 independent reflections
2737 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.02
4211 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.82 (3)	1.99 (3)	2.648 (3)	136 (2)
N3—H3⋯O4	0.83 (3)	2.01 (3)	2.632 (3)	132 (3)
N4—H4⋯O2ⁱ	0.82 (3)	2.48 (3)	3.290 (3)	170 (2)
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005662/bh2217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005662/bh2217Isup2.hkl

checkCIF report

Comment top

The title compound, C₂₂H₂₆N₄O₄S₂, was characterized by ¹H and ¹³C NMR, solid-state IR and X-ray crystallographic techniques. The X-ray structure determination reveals that the compound crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. The molecular geometry is illustrated in Fig. 1. The C—S bond lengths of 1.665 (3) Å and 1.659 (2) Å and the C—O bond lengths of 1.220 (3) Å and 1.222 (3) Å are double bonds character and are comparable to those observed for 1-(biphenyl-4-carbonyl)-3-p-tolyl-thiourea [1.647 (3) Å for C—S, 1.217 (3) and 1.224 (3) Å for C—O respectively (Arslan et al., 2004)]. The C—N bond lengths are in the range 1.310 (3)–1.451 (3) Å, and are shorter than the normal single C—N bond length (Avşar et al., 2003). The carbonyl group forms an intramolecular hydrogen bonds with the N2—H2 and the N3—H3 groups, which forms two six-membered rings (C8/N1/C7/O1/H2/N2 and C15/N4/C16/O4/H3/N3) structure (Fig. 2); H2···O1 and the H3···O4 separations are respectively 1.99 (3) Å and 2.01 (3) Å. There is an intermolecular hydrogen bonding between N4—H4 and the O atom of the ethoxy group of a symmetry-related molecule, the H4···O2 (-x + 2, -y, -z + 1) separation being 2.48 (3) Å (Table 1). The structure of the title compound is related to other thiourea derivatives (e.g. Ding et al., 2008; Du & Du, 2008).

Related literature top

For related structures, see: Avşar et al. (2003); Arslan et al. (2004); Du & Du (2008); Ding et al. (2008).

Experimental top

Benzoyl chloride (7.10 g, 50 mmol) was reacted with potassium thiocyanate (4.86 g, 50 mmol) in CH₃OCH₃ (50 ml) solution, to give the corresponding benzoyl isothiocyanate after one hour under refluxing. After cooling to room temperature, a solution of 2-(2-(2-aminoethoxy)ethoxy)ethanamine (3.70 g, 25 mmol) in CH₃OCH₃ (20 ml) was added dropwise to benzoyl isothiocyanate. After three hours under stirring, 200 ml of HCl 1 M was added. A yellow oil was isolated and treated with diethyl ether to give the title compound which is washed with diethyl ether twice. Yield: 55.9%. m.p. 415–419 K. Anal. Calc. for C₂₂H₂₆N₄O₄S₂: C 55.68, H 5.52, N 11.81%. Found: C 55.70, H 5.45, N 11.65%. Selected IR data (cm^-1, KBr pellet): 3424, 3218 (ν NH), 1667 (ν C?O), 1160 (ν C?S). ¹H-NMR (200 MHz, DMSO-d₆, δ, p.p.m.): 3.45 (t, 4H, N—CH₂); 3.63 (s, 4H, O—CH₂); 3.70 (t, 4H, O—CH₂); 7.21–7.92 (m, 10H, C₆H₅); 11.01 (s, 2H, NH); 11.41 (s, 2H, NH). ¹³C-NMR (50 MHz, DMSO-d₆, δ, p.p.m.): 45.21 (N—CH₂); 68.09 (O—CH₂); 70.12 (O—CH₂); 133.31–127.62 (C₆H₅); 1168.60 (C?O); 180.81 (C?S). A CH₃Cl solution of the title compound was mixed with ethanol (1/1). After several days, colorless block-shaped single crystals suitable for X-ray crystallographic analysis were obtained.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP view of the asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are plotted at the 50% probability level.
	Fig. 2. Molecular representation of the compound showing hydrogen bonds (dashed lines).

3,3'-Dibenzoyl-1,1'-(3,6-dioxaoctane-1,8-diyl)dithiourea top

Crystal data top

C₂₂H₂₆N₄O₄S₂	Z = 2
M_r = 474.59	F(000) = 500
Triclinic, P1	D_x = 1.347 Mg m⁻³
Hall symbol: -P 1	Melting point: 415 K
a = 7.9718 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2177 (3) Å	Cell parameters from 4206 reflections
c = 16.4106 (5) Å	θ = 1.0–25.4°
α = 81.018 (2)°	µ = 0.26 mm⁻¹
β = 83.364 (2)°	T = 293 K
γ = 80.450 (2)°	Prism, yellow
V = 1169.60 (6) Å³	0.10 × 0.10 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	2737 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 25.2°, θ_min = 2.3°
ω scans	h = −9→9
7989 measured reflections	k = −11→11
4211 independent reflections	l = −19→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0614P)² + 0.2609P] where P = (F_o² + 2F_c²)/3
4211 reflections	(Δ/σ)_max = 0.008
305 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³
0 constraints

Crystal data top

C₂₂H₂₆N₄O₄S₂	γ = 80.450 (2)°
M_r = 474.59	V = 1169.60 (6) Å³
Triclinic, P1	Z = 2
a = 7.9718 (2) Å	Mo Kα radiation
b = 9.2177 (3) Å	µ = 0.26 mm⁻¹
c = 16.4106 (5) Å	T = 293 K
α = 81.018 (2)°	0.10 × 0.10 × 0.10 mm
β = 83.364 (2)°

Data collection top

Nonius KappaCCD diffractometer	2737 reflections with I > 2σ(I)
7989 measured reflections	R_int = 0.030
4211 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.41 e Å⁻³
4211 reflections	Δρ_min = −0.50 e Å⁻³
305 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.37094 (10)	0.16706 (9)	0.86251 (5)	0.0713 (3)
S2	1.26452 (13)	−0.27342 (8)	0.52516 (4)	0.0790 (3)
O1	0.7377 (3)	0.4586 (2)	0.91685 (11)	0.0711 (6)
O2	0.81088 (19)	0.39803 (17)	0.67050 (9)	0.0482 (4)
O3	1.12041 (19)	0.24744 (17)	0.60508 (10)	0.0472 (4)
O4	1.2463 (3)	0.1608 (2)	0.35665 (11)	0.0740 (6)
N1	0.5641 (3)	0.2839 (3)	0.94678 (14)	0.0527 (6)
H1	0.530 (3)	0.224 (3)	0.9815 (16)	0.049 (8)*
N2	0.5680 (3)	0.3729 (2)	0.80784 (13)	0.0492 (5)
H2	0.639 (3)	0.422 (3)	0.8172 (16)	0.056 (8)*
N3	1.2498 (3)	0.0165 (3)	0.50822 (13)	0.0506 (5)
H3	1.236 (3)	0.099 (3)	0.4798 (17)	0.063 (9)*
N4	1.2073 (3)	−0.0786 (2)	0.39123 (12)	0.0465 (5)
H4	1.190 (3)	−0.154 (3)	0.3741 (15)	0.052 (8)*
C1	0.7116 (3)	0.3433 (3)	1.05616 (14)	0.0456 (6)
C2	0.8101 (3)	0.4370 (3)	1.08034 (16)	0.0539 (6)
H2A	0.8497	0.5115	1.0416	0.065*
C3	0.8498 (4)	0.4211 (3)	1.16088 (18)	0.0639 (7)
H3A	0.9169	0.4840	1.1763	0.077*
C4	0.7902 (4)	0.3120 (3)	1.21864 (18)	0.0692 (8)
H4A	0.8165	0.3012	1.2732	0.083*
C5	0.6923 (4)	0.2194 (4)	1.19573 (19)	0.0771 (9)
H5	0.6513	0.1464	1.2350	0.093*
C6	0.6537 (4)	0.2335 (3)	1.11472 (17)	0.0649 (8)
H6	0.5885	0.1690	1.0995	0.078*
C7	0.6744 (3)	0.3674 (3)	0.96796 (15)	0.0488 (6)
C8	0.5078 (3)	0.2817 (3)	0.86956 (15)	0.0477 (6)
C9	0.5275 (3)	0.3838 (3)	0.72324 (15)	0.0537 (6)
H9A	0.4095	0.4293	0.7189	0.064*
H9B	0.5406	0.2851	0.7075	0.064*
C10	0.6419 (3)	0.4745 (3)	0.66582 (15)	0.0516 (6)
H10A	0.6101	0.4859	0.6096	0.062*
H10B	0.6331	0.5723	0.6822	0.062*
C11	0.9346 (3)	0.4733 (3)	0.61860 (16)	0.0522 (6)
H11A	0.9278	0.5730	0.6320	0.063*
H11B	0.9133	0.4804	0.5610	0.063*
C12	1.1067 (3)	0.3882 (3)	0.63208 (16)	0.0506 (6)
H12A	1.1936	0.4426	0.6014	0.061*
H12B	1.1243	0.3751	0.6904	0.061*
C13	1.2832 (3)	0.1611 (3)	0.61572 (16)	0.0529 (6)
H13A	1.3092	0.1538	0.6727	0.063*
H13B	1.3705	0.2077	0.5799	0.063*
C14	1.2803 (3)	0.0091 (3)	0.59436 (14)	0.0504 (6)
H14A	1.3887	−0.0529	0.6045	0.061*
H14B	1.1912	−0.0359	0.6297	0.061*
C15	1.2389 (3)	−0.1016 (3)	0.47501 (14)	0.0447 (6)
C16	1.2118 (3)	0.0483 (3)	0.33592 (14)	0.0454 (6)
C17	1.1796 (3)	0.0433 (2)	0.24907 (14)	0.0419 (5)
C18	1.2227 (3)	0.1595 (3)	0.19018 (15)	0.0527 (6)
H18	1.2684	0.2361	0.2062	0.063*
C19	1.1984 (3)	0.1624 (3)	0.10851 (16)	0.0610 (7)
H19	1.2299	0.2398	0.0693	0.073*
C20	1.1281 (3)	0.0520 (3)	0.08436 (16)	0.0618 (7)
H20	1.1120	0.0546	0.0289	0.074*
C21	1.0811 (3)	−0.0632 (3)	0.14224 (16)	0.0605 (7)
H21	1.0324	−0.1378	0.1260	0.073*
C22	1.1069 (3)	−0.0672 (3)	0.22467 (15)	0.0507 (6)
H22	1.0751	−0.1446	0.2638	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0807 (5)	0.0781 (5)	0.0659 (5)	−0.0445 (4)	−0.0032 (4)	−0.0115 (4)
S2	0.1467 (8)	0.0464 (4)	0.0494 (4)	−0.0296 (5)	−0.0275 (5)	0.0059 (3)
O1	0.0906 (14)	0.0822 (14)	0.0503 (11)	−0.0502 (12)	−0.0123 (10)	0.0050 (10)
O2	0.0498 (10)	0.0443 (9)	0.0461 (9)	−0.0077 (8)	0.0014 (8)	0.0036 (7)
O3	0.0497 (10)	0.0457 (9)	0.0501 (10)	−0.0119 (8)	−0.0053 (7)	−0.0140 (8)
O4	0.1328 (18)	0.0430 (11)	0.0518 (11)	−0.0288 (11)	−0.0176 (11)	−0.0010 (9)
N1	0.0584 (14)	0.0572 (14)	0.0453 (13)	−0.0237 (11)	0.0023 (11)	−0.0054 (11)
N2	0.0468 (12)	0.0626 (14)	0.0431 (12)	−0.0214 (11)	0.0000 (10)	−0.0112 (10)
N3	0.0716 (15)	0.0397 (13)	0.0409 (12)	−0.0077 (11)	−0.0081 (10)	−0.0055 (10)
N4	0.0666 (14)	0.0372 (12)	0.0385 (11)	−0.0162 (10)	−0.0079 (9)	−0.0024 (9)
C1	0.0450 (13)	0.0445 (14)	0.0455 (14)	−0.0027 (11)	−0.0034 (11)	−0.0053 (11)
C2	0.0562 (15)	0.0556 (16)	0.0514 (15)	−0.0127 (13)	−0.0023 (12)	−0.0093 (12)
C3	0.0698 (18)	0.0677 (18)	0.0579 (17)	−0.0074 (15)	−0.0134 (14)	−0.0177 (15)
C4	0.076 (2)	0.078 (2)	0.0507 (17)	0.0048 (17)	−0.0169 (15)	−0.0081 (16)
C5	0.087 (2)	0.080 (2)	0.0591 (19)	−0.0181 (18)	−0.0171 (16)	0.0192 (16)
C6	0.0748 (19)	0.0598 (17)	0.0612 (18)	−0.0203 (15)	−0.0184 (15)	0.0077 (14)
C7	0.0483 (14)	0.0492 (15)	0.0496 (15)	−0.0124 (12)	−0.0012 (12)	−0.0062 (12)
C8	0.0461 (13)	0.0507 (15)	0.0486 (15)	−0.0121 (11)	0.0023 (11)	−0.0135 (12)
C9	0.0498 (15)	0.0667 (17)	0.0491 (15)	−0.0132 (13)	−0.0048 (12)	−0.0167 (13)
C10	0.0562 (15)	0.0521 (15)	0.0451 (14)	−0.0026 (12)	−0.0084 (12)	−0.0056 (12)
C11	0.0639 (16)	0.0404 (14)	0.0514 (15)	−0.0188 (12)	0.0041 (12)	0.0006 (11)
C12	0.0578 (15)	0.0444 (14)	0.0527 (15)	−0.0208 (12)	0.0023 (12)	−0.0082 (12)
C13	0.0527 (15)	0.0607 (16)	0.0485 (15)	−0.0100 (13)	−0.0065 (12)	−0.0144 (12)
C14	0.0612 (16)	0.0531 (15)	0.0379 (13)	−0.0040 (12)	−0.0102 (11)	−0.0100 (11)
C15	0.0512 (14)	0.0442 (14)	0.0399 (13)	−0.0115 (11)	−0.0051 (11)	−0.0044 (11)
C16	0.0543 (14)	0.0392 (14)	0.0426 (13)	−0.0097 (11)	−0.0041 (11)	−0.0023 (11)
C17	0.0440 (13)	0.0396 (13)	0.0399 (13)	−0.0052 (10)	−0.0027 (10)	−0.0009 (10)
C18	0.0591 (16)	0.0488 (15)	0.0492 (15)	−0.0153 (12)	−0.0033 (12)	0.0029 (12)
C19	0.0667 (18)	0.0656 (18)	0.0458 (16)	−0.0163 (15)	−0.0043 (13)	0.0132 (13)
C20	0.0631 (17)	0.080 (2)	0.0399 (14)	−0.0112 (15)	−0.0098 (13)	0.0033 (14)
C21	0.0691 (17)	0.0629 (17)	0.0527 (16)	−0.0161 (14)	−0.0134 (13)	−0.0059 (13)
C22	0.0572 (15)	0.0500 (15)	0.0434 (14)	−0.0135 (12)	−0.0065 (12)	0.0052 (11)

Geometric parameters (Å, º) top

S1—C8	1.665 (3)	C5—H5	0.9300
S2—C15	1.659 (2)	C6—H6	0.9300
O1—C7	1.220 (3)	C9—C10	1.492 (3)
O2—C10	1.417 (3)	C9—H9A	0.9700
O2—C11	1.424 (3)	C9—H9B	0.9700
O3—C12	1.419 (3)	C10—H10A	0.9700
O3—C13	1.419 (3)	C10—H10B	0.9700
O4—C16	1.222 (3)	C11—C12	1.485 (3)
N1—C7	1.366 (3)	C11—H11A	0.9700
N1—C8	1.396 (3)	C11—H11B	0.9700
N1—H1	0.79 (3)	C12—H12A	0.9700
N2—C8	1.311 (3)	C12—H12B	0.9700
N2—C9	1.446 (3)	C13—C14	1.501 (3)
N2—H2	0.82 (3)	C13—H13A	0.9700
N3—C15	1.310 (3)	C13—H13B	0.9700
N3—C14	1.451 (3)	C14—H14A	0.9700
N3—H3	0.83 (3)	C14—H14B	0.9700
N4—C16	1.367 (3)	C16—C17	1.486 (3)
N4—C15	1.404 (3)	C17—C22	1.382 (3)
N4—H4	0.82 (3)	C17—C18	1.386 (3)
C1—C6	1.382 (3)	C18—C19	1.372 (4)
C1—C2	1.387 (3)	C18—H18	0.9300
C1—C7	1.486 (3)	C19—C20	1.369 (4)
C2—C3	1.375 (4)	C19—H19	0.9300
C2—H2A	0.9300	C20—C21	1.380 (4)
C3—C4	1.376 (4)	C20—H20	0.9300
C3—H3A	0.9300	C21—C22	1.386 (4)
C4—C5	1.366 (4)	C21—H21	0.9300
C4—H4A	0.9300	C22—H22	0.9300
C5—C6	1.381 (4)

C10—O2—C11	113.12 (18)	H10A—C10—H10B	108.5
C12—O3—C13	112.15 (18)	O2—C11—C12	108.43 (19)
C7—N1—C8	129.4 (2)	O2—C11—H11A	110.0
C7—N1—H1	117.6 (19)	C12—C11—H11A	110.0
C8—N1—H1	112.9 (19)	O2—C11—H11B	110.0
C8—N2—C9	124.1 (2)	C12—C11—H11B	110.0
C8—N2—H2	117.9 (18)	H11A—C11—H11B	108.4
C9—N2—H2	117.9 (19)	O3—C12—C11	109.5 (2)
C15—N3—C14	122.6 (2)	O3—C12—H12A	109.8
C15—N3—H3	119 (2)	C11—C12—H12A	109.8
C14—N3—H3	118 (2)	O3—C12—H12B	109.8
C16—N4—C15	127.9 (2)	C11—C12—H12B	109.8
C16—N4—H4	118.1 (18)	H12A—C12—H12B	108.2
C15—N4—H4	113.8 (18)	O3—C13—C14	108.6 (2)
C6—C1—C2	118.7 (2)	O3—C13—H13A	110.0
C6—C1—C7	123.7 (2)	C14—C13—H13A	110.0
C2—C1—C7	117.6 (2)	O3—C13—H13B	110.0
C3—C2—C1	120.8 (3)	C14—C13—H13B	110.0
C3—C2—H2A	119.6	H13A—C13—H13B	108.4
C1—C2—H2A	119.6	N3—C14—C13	111.0 (2)
C2—C3—C4	119.8 (3)	N3—C14—H14A	109.4
C2—C3—H3A	120.1	C13—C14—H14A	109.4
C4—C3—H3A	120.1	N3—C14—H14B	109.4
C5—C4—C3	119.9 (3)	C13—C14—H14B	109.4
C5—C4—H4A	120.0	H14A—C14—H14B	108.0
C3—C4—H4A	120.0	N3—C15—N4	116.7 (2)
C4—C5—C6	120.5 (3)	N3—C15—S2	124.06 (19)
C4—C5—H5	119.7	N4—C15—S2	119.18 (18)
C6—C5—H5	119.7	O4—C16—N4	121.1 (2)
C5—C6—C1	120.2 (3)	O4—C16—C17	121.1 (2)
C5—C6—H6	119.9	N4—C16—C17	117.8 (2)
C1—C6—H6	119.9	C22—C17—C18	119.0 (2)
O1—C7—N1	121.3 (2)	C22—C17—C16	124.1 (2)
O1—C7—C1	121.7 (2)	C18—C17—C16	116.9 (2)
N1—C7—C1	117.0 (2)	C19—C18—C17	120.5 (3)
N2—C8—N1	116.1 (2)	C19—C18—H18	119.8
N2—C8—S1	125.2 (2)	C17—C18—H18	119.8
N1—C8—S1	118.66 (18)	C20—C19—C18	120.4 (2)
N2—C9—C10	110.6 (2)	C20—C19—H19	119.8
N2—C9—H9A	109.5	C18—C19—H19	119.8
C10—C9—H9A	109.5	C19—C20—C21	120.1 (3)
N2—C9—H9B	109.5	C19—C20—H20	120.0
C10—C9—H9B	109.5	C21—C20—H20	120.0
H9A—C9—H9B	108.1	C20—C21—C22	119.7 (3)
O2—C10—C9	107.14 (19)	C20—C21—H21	120.1
O2—C10—H10A	110.3	C22—C21—H21	120.1
C9—C10—H10A	110.3	C17—C22—C21	120.3 (2)
O2—C10—H10B	110.3	C17—C22—H22	119.8
C9—C10—H10B	110.3	C21—C22—H22	119.8

O2—C11—C12—O3	65.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (3)	1.99 (3)	2.648 (3)	136 (2)
N3—H3···O4	0.83 (3)	2.01 (3)	2.632 (3)	132 (3)
N4—H4···O2ⁱ	0.82 (3)	2.48 (3)	3.290 (3)	170 (2)

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆N₄O₄S₂
M_r	474.59
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9718 (2), 9.2177 (3), 16.4106 (5)
α, β, γ (°)	81.018 (2), 83.364 (2), 80.450 (2)
V (Å³)	1169.60 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7989, 4211, 2737
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.02
No. of reflections	4211
No. of parameters	305
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.50

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (3)	1.99 (3)	2.648 (3)	136 (2)
N3—H3···O4	0.83 (3)	2.01 (3)	2.632 (3)	132 (3)
N4—H4···O2ⁱ	0.82 (3)	2.48 (3)	3.290 (3)	170 (2)

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

The authors thank the Agence Universitaire de la Francophonie for financial support (AUF-PSCI No.6314PS804).

References

Arslan, H., Flörke, U. & Külcü, N. (2004). Acta Chim. Slov. 51, 787–792. CAS Google Scholar
Avşar, G., Arslan, H., Haupt, H.-J. & Külcü, N. (2003). Turk. J. Chem. 27, 281–285. Google Scholar
Ding, Y.-J., Chang, X.-B., Yang, X.-Q. & Dong, W.-K. (2008). Acta Cryst. E64, o658. Web of Science CSD CrossRef IUCr Journals Google Scholar
Du, H.-T. & Du, H.-J. (2008). Acta Cryst. E64, o1632–o1633. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar