1,2-Bis(N′-benzoyl­thio­ureido)benzene

Thiam, E.I.; Diop, M.; Gaye, M.; Sall, A.S.; Barry, A.H.

doi:10.1107/S1600536808008374

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o776

doi:10.1107/S1600536808008374

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1,2-Bis(N′-benzoylthioureido)benzene

Elhadj Ibrahima Thiam,^a Mayoro Diop,^a Mohamed Gaye,^a Abdou Salam Sall ^a and Aliou Hamady Barry ^b ^*

^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 18 February 2008; accepted 27 March 2008; online 2 April 2008)

The title compound, C₂₂H₁₈N₄O₂S₂, was characterized by ¹H and ¹³C NMR, solid-state IR spectroscopy and X-ray crystallographic techniques. The crystal structure determination reveals that the twisting modes of the two side arms are different [C—N—C—O and C—N—C—N torsion angles = −1.2 (3) and 1.1 (3)°, respectively, in one arm and 24.1 (3) and −5.1 (3)°, respectively, in the other]. The crystal structure involves N—H⋯O and N—H⋯S hydrogen bonds.

Related literature

For related structures: see Arslan et al. (2004 ); Avşar et al. (2003 ).

Experimental

Crystal data

C₂₂H₁₈N₄O₂S₂
M_r = 434.52
Triclinic, $[P \overline 1]$
a = 7.179 (1) Å
b = 12.064 (2) Å
c = 12.476 (2) Å
α = 77.88 (5)°
β = 86.96 (5)°
γ = 77.91 (5)°
V = 1032.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 (2) K
0.10 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
12922 measured reflections
4671 independent reflections
3234 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.118
S = 1.04
4671 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O6	0.88	1.88	2.633 (2)	142
N2—HN2⋯O7	0.88	1.99	2.680 (2)	134
N4—HN4⋯S2ⁱ	0.88	2.61	3.478 (2)	170
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008374/ww2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008374/ww2115Isup2.hkl

checkCIF report

Comment top

The title compound, C₂₂H₁₈N₄O₂S₂, 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 P-1 with one molecule in the asymmetric unit. The molecular geometry is illustrated in Fig. 1. The S1—C1 [1.6574 (18)Å], the S2—C8 [1.660 (2)Å], the O7—C16 [1.219 (2)Å] and O6—C9 [1.222 (2)Å] distances indicates that these correspond to double bonds 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 [1.335 (2) - 1.435 (2)Å] and are shorter than the normal single C—N bond length, indicating double bond character (Avşar et al., 2003). The two side arms are not twisted in the same way. One of the arms is slightly twisted as reflected by the two torsion angle C1—N3—C9—O6 [-1.2 (3)°] and C9—N3—C1—N1 [1.1 (3) °]. The torsion angles C8—N4—C16—O7 [24.1 (3)°] and C16—N4—C8—N2 [-5.1 (3)°] in the other side arm indicate that this one is more strongly twisted. Intramolecular hydrogen-bond contacts involve the NH groups and the O atoms of the amide groups as well as the N atoms of the thiourea groups while intermolecular hydrogen-bond is observed between the NH groups and the S atoms of the thiourea groups (Table 2)

Related literature top

For related structures: see Arslan et al. (2004); Avşar et al. (2003).

Experimental top

All purchased chemicals and solvents were reagent grade and used without further purifcation. Melting points were determined with a Büchi 570 melting-point apparatus and were uncorrected. The ¹H NMR spectra were measured with a Bruker AM-400 spectrometer, using tetramethylsilane as the internal standard. The solid-state IR spectra were recorded from KBr discs on a Nicolet spectrophotometer. To a mixture of 9.718 g (100 mmol) of potassium thiocyanate and 100 ml of acetone was added dropwise a solution of 14.071 g (100 mmol) of benzoyl chloride in 50 ml of acetone. The resulting mixture was stirred under reflux for 1 h and cooled to room temperature. A solution of 5.407 g (50 mmol) of 1,2-diaminobenzene in 20 ml of acetone was added. The yellow solution obtained was stirred at room temperature during 2 h. 300 ml of 1 N HCl was added to dissolve the precipitated KCl. A white solid appeared after five minutes. The compound was filtered and washed with 3 x 50 ml of water and dried under vacuum. Recrystallization from a mixture of methanol and chloroform (1:1) gave 18.52 g (85.7%) of the title compound. M.p. 360±362 K (uncorrected. Mass spectrum, m/z= 434 (M⁺). ¹H NMR (CDCl₃): δ 7.38–7.93 (m, 14H, ArH), 9.30 (s, 2H, SH), 12.36 (s, 2H, OH); ¹³C NMR (CDCl₃): δ 126.97, 127.70, 128.15, 129.10, 131.14, 131.60, 133.10, 166.90, 180. IR (cm^-1,KBr): 3210, 1673, 1596, 1470, 1319, 1262, 1149, 857, 688. Analysis calculated for C₂₂H₁₈N₄O₂S₂: C 60.81, H 4.18, N 12.89, S 14.76%; found: C 60.80, H 4.59, N 12.87, S 14.80%. Monocrystals suitable for X-ray analysis was obtained from slow evaporation of a dimethylformamide solution of the product.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Nonius, 1998); data reduction: DENZO (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); 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. The tautomerism in the title compound.

1,2-Bis(N'-benzoylthioureido)benzene top

Crystal data top

C₂₂H₁₈N₄O₂S₂	Z = 2
M_r = 434.52	F(000) = 452
Triclinic, P1	D_x = 1.397 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.179 (1) Å	Cell parameters from 6418 reflections
b = 12.064 (2) Å	θ = 1.0–27.5°
c = 12.476 (2) Å	µ = 0.29 mm⁻¹
α = 77.88 (5)°	T = 173 K
β = 86.96 (5)°	Prism, colorless
γ = 77.91 (5)°	0.10 × 0.10 × 0.10 mm
V = 1032.9 (3) Å³

Data collection top

Nonius KappaCCD diffractometer	3234 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.047
Graphite monochromator	θ_max = 27.4°, θ_min = 3.1°
ω scans	h = −9→8
12922 measured reflections	k = −15→15
4671 independent reflections	l = −16→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.048P)² + 0.1332P] where P = (F_o² + 2F_c²)/3
4671 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₂H₁₈N₄O₂S₂	γ = 77.91 (5)°
M_r = 434.52	V = 1032.9 (3) Å³
Triclinic, P1	Z = 2
a = 7.179 (1) Å	Mo Kα radiation
b = 12.064 (2) Å	µ = 0.29 mm⁻¹
c = 12.476 (2) Å	T = 173 K
α = 77.88 (5)°	0.10 × 0.10 × 0.10 mm
β = 86.96 (5)°

Data collection top

Nonius KappaCCD diffractometer	3234 reflections with I > 2σ(I)
12922 measured reflections	R_int = 0.047
4671 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
4671 reflections	Δρ_min = −0.24 e Å⁻³
271 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	0.51586 (8)	0.37259 (4)	0.93513 (5)	0.0727 (2)
S2	0.83170 (8)	0.17089 (4)	0.50551 (4)	0.06579 (18)
O6	0.69327 (18)	0.01181 (10)	0.86202 (10)	0.0574 (3)
O7	0.5045 (2)	−0.09194 (11)	0.70005 (13)	0.0680 (4)
N1	0.5437 (2)	0.23196 (11)	0.78892 (12)	0.0473 (3)
HN1	0.5932	0.1610	0.7809	0.057*
N2	0.5204 (2)	0.12967 (12)	0.61750 (12)	0.0529 (4)
HN2	0.4517	0.0797	0.6504	0.064*
N3	0.6479 (2)	0.15035 (12)	0.96355 (12)	0.0515 (4)
HN3	0.6623	0.1608	1.0301	0.062*
N4	0.7603 (2)	−0.02950 (12)	0.61097 (12)	0.0536 (4)
HN4	0.8699	−0.0573	0.5818	0.064*
C1	0.5672 (2)	0.25055 (15)	0.88870 (15)	0.0487 (4)
C2	0.4547 (2)	0.30447 (14)	0.69408 (14)	0.0464 (4)
C3	0.3759 (3)	0.42184 (16)	0.68239 (17)	0.0617 (5)
H3	0.3854	0.4605	0.7402	0.074*
C4	0.2842 (3)	0.48218 (17)	0.5872 (2)	0.0740 (6)
H4	0.2306	0.5623	0.5801	0.089*
C5	0.2688 (3)	0.4288 (2)	0.5025 (2)	0.0798 (7)
H5	0.2044	0.4713	0.4374	0.096*
C6	0.3477 (3)	0.31235 (19)	0.51256 (18)	0.0724 (6)
H6	0.3376	0.2747	0.4541	0.087*
C7	0.4408 (3)	0.25085 (15)	0.60686 (15)	0.0516 (4)
C8	0.6935 (3)	0.08886 (14)	0.58002 (13)	0.0499 (4)
C9	0.7082 (2)	0.03836 (14)	0.95003 (14)	0.0432 (4)
C10	0.7920 (2)	−0.04822 (14)	1.04687 (14)	0.0439 (4)
C11	0.8139 (3)	−0.02222 (17)	1.14823 (16)	0.0581 (5)
H11	0.7708	0.0548	1.1588	0.070*
C12	0.8976 (3)	−0.1075 (2)	1.23359 (17)	0.0704 (6)
H12	0.9132	−0.0886	1.3023	0.084*
C13	0.9583 (3)	−0.2187 (2)	1.22008 (19)	0.0710 (6)
H13	1.0160	−0.2770	1.2792	0.085*
C14	0.9358 (3)	−0.24622 (18)	1.1207 (2)	0.0716 (6)
H14	0.9773	−0.3237	1.1113	0.086*
C15	0.8529 (3)	−0.16125 (16)	1.03435 (16)	0.0577 (5)
H15	0.8377	−0.1808	0.9659	0.069*
C16	0.6757 (3)	−0.10936 (15)	0.68221 (15)	0.0526 (4)
C17	0.8076 (3)	−0.21596 (14)	0.73653 (14)	0.0489 (4)
C18	0.9977 (3)	−0.21949 (15)	0.75364 (15)	0.0553 (5)
H18	1.0507	−0.1534	0.7249	0.066*
C19	1.1108 (3)	−0.31812 (19)	0.81204 (17)	0.0675 (5)
H19	1.2411	−0.3196	0.8238	0.081*
C20	1.0355 (4)	−0.41383 (19)	0.85309 (19)	0.0795 (7)
H20	1.1136	−0.4819	0.8931	0.095*
C21	0.8486 (4)	−0.41166 (18)	0.8367 (2)	0.0851 (7)
H21	0.7973	−0.4784	0.8656	0.102*
C22	0.7330 (3)	−0.31380 (17)	0.77883 (18)	0.0671 (5)
H22	0.6028	−0.3132	0.7679	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0863 (4)	0.0478 (3)	0.0852 (4)	0.0036 (3)	−0.0164 (3)	−0.0301 (3)
S2	0.0795 (4)	0.0420 (3)	0.0619 (3)	0.0045 (2)	0.0121 (3)	0.0005 (2)
O6	0.0759 (9)	0.0422 (7)	0.0499 (7)	0.0008 (6)	−0.0060 (6)	−0.0115 (6)
O7	0.0617 (9)	0.0473 (8)	0.0933 (11)	−0.0070 (7)	−0.0039 (7)	−0.0139 (7)
N1	0.0511 (8)	0.0349 (7)	0.0515 (9)	0.0007 (6)	0.0017 (6)	−0.0090 (6)
N2	0.0600 (9)	0.0381 (8)	0.0557 (9)	−0.0012 (7)	−0.0002 (7)	−0.0074 (7)
N3	0.0593 (9)	0.0430 (8)	0.0502 (9)	0.0006 (7)	−0.0080 (7)	−0.0139 (7)
N4	0.0681 (10)	0.0359 (8)	0.0503 (9)	0.0028 (7)	0.0040 (7)	−0.0085 (7)
C1	0.0435 (9)	0.0428 (10)	0.0598 (11)	−0.0055 (7)	0.0006 (8)	−0.0136 (8)
C2	0.0430 (9)	0.0369 (9)	0.0525 (10)	−0.0003 (7)	0.0050 (8)	−0.0031 (8)
C3	0.0693 (13)	0.0397 (10)	0.0671 (13)	0.0032 (9)	0.0049 (10)	−0.0062 (9)
C4	0.0797 (15)	0.0424 (11)	0.0831 (16)	0.0110 (10)	0.0013 (12)	0.0008 (11)
C5	0.0891 (16)	0.0591 (13)	0.0713 (15)	0.0162 (12)	−0.0161 (12)	0.0041 (11)
C6	0.0861 (15)	0.0581 (13)	0.0622 (13)	0.0073 (11)	−0.0157 (11)	−0.0064 (10)
C7	0.0535 (10)	0.0379 (9)	0.0553 (11)	0.0037 (8)	0.0004 (8)	−0.0049 (8)
C8	0.0668 (12)	0.0384 (9)	0.0400 (9)	0.0022 (8)	−0.0079 (8)	−0.0088 (7)
C9	0.0383 (9)	0.0412 (9)	0.0501 (10)	−0.0093 (7)	0.0036 (7)	−0.0091 (8)
C10	0.0332 (8)	0.0460 (10)	0.0506 (10)	−0.0102 (7)	0.0046 (7)	−0.0043 (8)
C11	0.0636 (12)	0.0558 (12)	0.0549 (11)	−0.0167 (10)	−0.0032 (9)	−0.0061 (9)
C12	0.0716 (14)	0.0806 (16)	0.0575 (12)	−0.0253 (12)	−0.0119 (10)	0.0019 (11)
C13	0.0523 (12)	0.0764 (16)	0.0692 (15)	−0.0135 (11)	−0.0067 (10)	0.0209 (12)
C14	0.0662 (13)	0.0516 (12)	0.0828 (16)	0.0014 (10)	0.0049 (11)	0.0031 (11)
C15	0.0589 (12)	0.0489 (11)	0.0595 (12)	−0.0048 (9)	0.0052 (9)	−0.0053 (9)
C16	0.0672 (13)	0.0398 (10)	0.0523 (11)	−0.0073 (9)	−0.0018 (9)	−0.0159 (8)
C17	0.0652 (12)	0.0359 (9)	0.0435 (9)	−0.0045 (8)	0.0058 (8)	−0.0108 (7)
C18	0.0713 (13)	0.0439 (10)	0.0480 (10)	−0.0079 (9)	0.0011 (9)	−0.0078 (8)
C19	0.0661 (13)	0.0658 (13)	0.0600 (12)	0.0041 (11)	0.0022 (10)	−0.0071 (10)
C20	0.0836 (17)	0.0568 (13)	0.0730 (15)	0.0153 (12)	0.0142 (12)	0.0095 (11)
C21	0.0904 (18)	0.0458 (12)	0.1012 (18)	−0.0055 (12)	0.0261 (14)	0.0099 (12)
C22	0.0682 (13)	0.0479 (11)	0.0770 (14)	−0.0055 (10)	0.0124 (11)	−0.0044 (10)

Geometric parameters (Å, º) top

S1—C1	1.6574 (18)	C6—H6	0.9500
S2—C8	1.660 (2)	C9—C10	1.482 (2)
O6—C9	1.222 (2)	C10—C15	1.381 (3)
O7—C16	1.219 (2)	C10—C11	1.390 (3)
N1—C1	1.335 (2)	C11—C12	1.379 (3)
N1—C2	1.409 (2)	C11—H11	0.9500
N1—HN1	0.8800	C12—C13	1.364 (3)
N2—C8	1.336 (2)	C12—H12	0.9500
N2—C7	1.435 (2)	C13—C14	1.375 (3)
N2—HN2	0.8800	C13—H13	0.9500
N3—C9	1.373 (2)	C14—C15	1.384 (3)
N3—C1	1.400 (2)	C14—H14	0.9500
N3—HN3	0.8800	C15—H15	0.9500
N4—C16	1.384 (2)	C16—C17	1.484 (3)
N4—C8	1.385 (2)	C17—C18	1.383 (3)
N4—HN4	0.8800	C17—C22	1.390 (3)
C2—C3	1.390 (3)	C18—C19	1.379 (3)
C2—C7	1.395 (3)	C18—H18	0.9500
C3—C4	1.376 (3)	C19—C20	1.368 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.368 (3)	C20—C21	1.361 (3)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.382 (3)	C21—C22	1.378 (3)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.375 (3)	C22—H22	0.9500

C1—N1—C2	132.18 (15)	C15—C10—C11	118.55 (18)
C1—N1—HN1	113.9	C15—C10—C9	117.42 (16)
C2—N1—HN1	113.9	C11—C10—C9	124.03 (16)
C8—N2—C7	123.32 (15)	C12—C11—C10	120.43 (19)
C8—N2—HN2	118.3	C12—C11—H11	119.8
C7—N2—HN2	118.3	C10—C11—H11	119.8
C9—N3—C1	130.47 (15)	C13—C12—C11	120.5 (2)
C9—N3—HN3	114.8	C13—C12—H12	119.7
C1—N3—HN3	114.8	C11—C12—H12	119.7
C16—N4—C8	127.91 (16)	C12—C13—C14	119.8 (2)
C16—N4—HN4	116.0	C12—C13—H13	120.1
C8—N4—HN4	116.0	C14—C13—H13	120.1
N1—C1—N3	113.59 (14)	C13—C14—C15	120.1 (2)
N1—C1—S1	129.80 (15)	C13—C14—H14	119.9
N3—C1—S1	116.61 (13)	C15—C14—H14	119.9
C3—C2—C7	118.45 (17)	C10—C15—C14	120.55 (19)
C3—C2—N1	125.64 (17)	C10—C15—H15	119.7
C7—C2—N1	115.87 (15)	C14—C15—H15	119.7
C4—C3—C2	120.1 (2)	O7—C16—N4	121.91 (18)
C4—C3—H3	119.9	O7—C16—C17	122.55 (18)
C2—C3—H3	119.9	N4—C16—C17	115.53 (17)
C5—C4—C3	121.14 (19)	C18—C17—C22	118.80 (18)
C5—C4—H4	119.4	C18—C17—C16	122.79 (16)
C3—C4—H4	119.4	C22—C17—C16	118.25 (17)
C4—C5—C6	119.4 (2)	C19—C18—C17	120.57 (18)
C4—C5—H5	120.3	C19—C18—H18	119.7
C6—C5—H5	120.3	C17—C18—H18	119.7
C7—C6—C5	120.3 (2)	C20—C19—C18	120.0 (2)
C7—C6—H6	119.9	C20—C19—H19	120.0
C5—C6—H6	119.9	C18—C19—H19	120.0
C6—C7—C2	120.62 (17)	C21—C20—C19	120.1 (2)
C6—C7—N2	120.04 (18)	C21—C20—H20	120.0
C2—C7—N2	119.32 (16)	C19—C20—H20	120.0
N2—C8—N4	116.00 (17)	C20—C21—C22	120.8 (2)
N2—C8—S2	124.29 (13)	C20—C21—H21	119.6
N4—C8—S2	119.66 (14)	C22—C21—H21	119.6
O6—C9—N3	121.30 (16)	C21—C22—C17	119.7 (2)
O6—C9—C10	121.83 (15)	C21—C22—H22	120.1
N3—C9—C10	116.87 (15)	C17—C22—H22	120.1

C2—N1—C1—N3	173.63 (15)	N3—C9—C10—C15	179.91 (15)
C2—N1—C1—S1	−6.5 (3)	O6—C9—C10—C11	179.29 (16)
C9—N3—C1—N1	1.1 (3)	N3—C9—C10—C11	−0.6 (2)
C9—N3—C1—S1	−178.77 (14)	C15—C10—C11—C12	1.1 (3)
C1—N1—C2—C3	4.2 (3)	C9—C10—C11—C12	−178.39 (16)
C1—N1—C2—C7	−173.60 (17)	C10—C11—C12—C13	−0.7 (3)
C7—C2—C3—C4	1.0 (3)	C11—C12—C13—C14	0.0 (3)
N1—C2—C3—C4	−176.74 (18)	C12—C13—C14—C15	0.4 (3)
C2—C3—C4—C5	−0.1 (3)	C11—C10—C15—C14	−0.7 (3)
C3—C4—C5—C6	−0.4 (4)	C9—C10—C15—C14	178.77 (16)
C4—C5—C6—C7	0.0 (4)	C13—C14—C15—C10	0.0 (3)
C5—C6—C7—C2	0.9 (3)	C8—N4—C16—O7	24.1 (3)
C5—C6—C7—N2	179.2 (2)	C8—N4—C16—C17	−154.85 (16)
C3—C2—C7—C6	−1.4 (3)	O7—C16—C17—C18	−153.22 (18)
N1—C2—C7—C6	176.58 (18)	N4—C16—C17—C18	25.7 (2)
C3—C2—C7—N2	−179.69 (16)	O7—C16—C17—C22	22.0 (3)
N1—C2—C7—N2	−1.7 (2)	N4—C16—C17—C22	−159.06 (17)
C8—N2—C7—C6	85.3 (2)	C22—C17—C18—C19	−0.3 (3)
C8—N2—C7—C2	−96.4 (2)	C16—C17—C18—C19	174.92 (17)
C7—N2—C8—N4	170.75 (15)	C17—C18—C19—C20	0.4 (3)
C7—N2—C8—S2	−6.4 (2)	C18—C19—C20—C21	−0.3 (3)
C16—N4—C8—N2	−5.1 (3)	C19—C20—C21—C22	0.1 (4)
C16—N4—C8—S2	172.23 (14)	C20—C21—C22—C17	0.0 (4)
C1—N3—C9—O6	−1.2 (3)	C18—C17—C22—C21	0.1 (3)
C1—N3—C9—C10	178.76 (15)	C16—C17—C22—C21	−175.32 (19)
O6—C9—C10—C15	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O6	0.88	1.88	2.633 (2)	141.8
N2—HN2···O7	0.88	1.99	2.680 (2)	133.9
N4—HN4···S2ⁱ	0.88	2.61	3.478 (2)	169.9

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₄O₂S₂
M_r	434.52
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.179 (1), 12.064 (2), 12.476 (2)
α, β, γ (°)	77.88 (5), 86.96 (5), 77.91 (5)
V (Å³)	1032.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
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	12922, 4671, 3234
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.118, 1.04
No. of reflections	4671
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24

Computer programs: COLLECT (Nonius, 1998), DENZO (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

S1—C1	1.6574 (18)	N2—C8	1.336 (2)
S2—C8	1.660 (2)	N2—C7	1.435 (2)
O6—C9	1.222 (2)	N3—C9	1.373 (2)
O7—C16	1.219 (2)	N3—C1	1.400 (2)
N1—C1	1.335 (2)	N4—C16	1.384 (2)
N1—C2	1.409 (2)	N4—C8	1.385 (2)

C1—N1—C2	132.18 (15)	N2—C8—S2	124.29 (13)
C8—N2—C7	123.32 (15)	N4—C8—S2	119.66 (14)
C9—N3—C1	130.47 (15)	O6—C9—N3	121.30 (16)
C16—N4—C8	127.91 (16)	O6—C9—C10	121.83 (15)
N1—C1—S1	129.80 (15)	O7—C16—N4	121.91 (18)
N3—C1—S1	116.61 (13)	O7—C16—C17	122.55 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O6	0.88	1.88	2.633 (2)	141.8
N2—HN2···O7	0.88	1.99	2.680 (2)	133.9
N4—HN4···S2ⁱ	0.88	2.61	3.478 (2)	169.9

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

The authors thank the Fondation SONATEL for financial support (CDP 75/06) and Professor R. Welter (Laboratoire DECOMET, UMR CNRS, Université Louis Pasteur 4, Strasbourg, France) for assistance.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar