1,2-Bis(N′-benzoyl­thio­ureido)-4-chloro­benzene

Yamin, B.M.; Osman, U.M.

doi:10.1107/S1600536811014954

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1286

doi:10.1107/S1600536811014954

Open

access

1,2-Bis(N′-benzoylthioureido)-4-chlorobenzene

Bohari M. Yamin ^a ^* and Uwaisulqarni M. Osman ^a

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia
^*Correspondence e-mail: bohari@ukm.my

(Received 20 April 2011; accepted 20 April 2011; online 7 May 2011)

In the title compound, C₂₂H₁₇ClN₄O₂S₂, both benzoyl groups are trans to the thiono group across their C—N bonds. The two methylene carbamothioyl formamide fragments of the benzoylthiourea side arms make a dihedral angle of 87.00 (10)°. The molecule is stabilized by intramolecular N—H⋯O, N—H⋯S and C—H⋯·S hydrogen bonds. In the crystal, molecules are linked by N—H⋯O and N—H⋯S intermolecular hydrogen bonds into zigzag chains along the a axis.

Related literature

For the structure of related biscarbomothioyl thiourea compounds, see: Thiam et al. (2008 ); Yusof et al. (2008 ); Woei Hung & Kassim (2010 ). For bond length data, see: Allen (2002 ).

Experimental

Crystal data

C₂₂H₁₇ClN₄O₂S₂
M_r = 468.97
Triclinic, $[P \overline 1]$
a = 9.637 (4) Å
b = 10.820 (4) Å
c = 11.370 (4) Å
α = 84.443 (8)°
β = 68.706 (8)°
γ = 86.551 (9)°
V = 1099.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 298 K
0.49 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.928, T_max = 0.965
12132 measured reflections
4083 independent reflections
3107 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.173
S = 1.08
4083 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S2	0.86	2.86	3.443 (4)	127
N2—H2A⋯O1	0.86	1.91	2.621 (5)	140
N3—H3A⋯O2	0.86	1.96	2.642 (3)	135
C10—H10A⋯S1	0.93	2.61	3.173 (5)	120
N1—H1A⋯O2ⁱ	0.86	2.51	3.328 (5)	159
N4—H4A⋯S2ⁱⁱ	0.86	2.81	3.476 (4)	136
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014954/ff2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014954/ff2008Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811014954/ff2008Isup3.cml

checkCIF report

Comment top

Bis-carbonoyl thiourea compounds are relatively less reported than their mono-carbonoyl thiourea derivatives. The title compound contains two benzoyl thioureido groups connected by 4-chlorobenzene bridge at 1, 2 position (Fig.1). The C7—O1 and C16—O2 bond lengths in the both side arms of 1.220 (5) and 1.230 (5) Å, respectively, are slightly longer than the normal C=O double bonds (1.200 Å) and comparable to those in 1,2-bis(N'-benzoylthioureido)benzene (Thiam et al. 2008) and 1-benzoyl-3-[4-(3-benzoylthioureido)-phenyl]thiourea (Woei Hung & Kassim 2010). Other bond lengths and angles are in normal ranges (Allen, 2002). Both methylene carbamothioyl formamide, S1/O1/N1/N2/C6/C7/C8/C9 and S2/O2/N3/N4/C14/C15/C16 fragments of the benzoyl thiourea side arms are planar with maximum deviation of 0.060 (3)Å for O1 atom and make dihedral angles of 87.00 (10)°. The dihedral angle between (C1—C6) and (C17—C22) benzene rings is 86.4 (2)° to each other. There are four intramolecular hydrogen bonds forming three pseudo-six-membered ring [S1···H10A—C10—C9—N2—C8], [O1···H2A—N2—C8—N1—C7] and [O2···H3A—N3—C15—N4—C16] and one pseudo-seven-membered ring [S2···H2A—N2—C9—C14—N3—C15] as compared to two intramolecular hydrogen bonds observed in 1,2-bis(N'-benzoylthioureido) benzene (Thiam et al. 2008) and 1,2-bis[N'-(2,2-dimethylpropionyl)thioureido] cyclohexane (Yusof et al. 2008). In the crystal structure, the molecules are linked by N1—H1A···O2 and N4—H4A···S2 intermolecular hydrogen bonds (symmetry codes as in Table 2) into a zigzag chains along the a axis.

Related literature top

For the structure of related biscarbomothioyl thiourea compounds, see: Thiam et al. (2008); Yusof et al. (2008); Woei Hung & Kassim (2010). For bond length data, see: Allen (2002).

Experimental top

To a stirring acetone solution (75 ml) of benzoyl chloride (0.04 mol) and ammonium thiocyanate (0.04 mol). 4-chlorobenzene-1,2-diamine (0.02 mol) in 40 ml of acetone was added dropwise. The solution mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice cubes. The white precipitate was filtered off and washed with distilled water and cold ethanol before dried under vacuum. Good quality crystals were obtained by recrystallization from ethanol.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the a-axis. Hydrogen bonds are shown by dashed lines.

1-Benzoyl-3-[2-(N'-benzoylthioureido)-5-chlorophenyl]thiourea top

Crystal data top

C₂₂H₁₇ClN₄O₂S₂	Z = 2
M_r = 468.97	F(000) = 484
Triclinic, P1	D_x = 1.417 Mg m⁻³
Hall symbol: -P 1	Melting point = 458.5–459.5 K
a = 9.637 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.820 (4) Å	Cell parameters from 2481 reflections
c = 11.370 (4) Å	θ = 1.8–25.5°
α = 84.443 (8)°	µ = 0.39 mm⁻¹
β = 68.706 (8)°	T = 298 K
γ = 86.551 (9)°	Plate, colourless
V = 1099.1 (7) Å³	0.49 × 0.16 × 0.09 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4083 independent reflections
Radiation source: fine-focus sealed tube	3107 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.5°, θ_min = 1.8°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→13
T_min = 0.928, T_max = 0.965	l = −13→13
12132 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0812P)² + 0.6319P] where P = (F_o² + 2F_c²)/3
4083 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₁₇ClN₄O₂S₂	γ = 86.551 (9)°
M_r = 468.97	V = 1099.1 (7) Å³
Triclinic, P1	Z = 2
a = 9.637 (4) Å	Mo Kα radiation
b = 10.820 (4) Å	µ = 0.39 mm⁻¹
c = 11.370 (4) Å	T = 298 K
α = 84.443 (8)°	0.49 × 0.16 × 0.09 mm
β = 68.706 (8)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4083 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3107 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.965	R_int = 0.042
12132 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.08	Δρ_max = 0.79 e Å⁻³
4083 reflections	Δρ_min = −0.30 e Å⁻³
280 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
Cl1	0.16623 (15)	0.60564 (10)	0.11914 (13)	0.0845 (4)
S1	−0.13518 (13)	0.32671 (13)	0.50891 (12)	0.0882 (5)
S2	0.50891 (11)	0.17508 (8)	0.38266 (10)	0.0524 (3)
O1	0.1820 (3)	0.0277 (3)	0.5716 (3)	0.0866 (11)
O2	0.3898 (3)	−0.1381 (2)	0.2029 (3)	0.0570 (7)
N1	−0.0285 (3)	0.1455 (3)	0.6212 (3)	0.0504 (7)
H1A	−0.1142	0.1557	0.6795	0.060*
N2	0.1368 (3)	0.2180 (3)	0.4276 (3)	0.0486 (7)
H2A	0.1939	0.1630	0.4482	0.058*
N3	0.3678 (3)	0.1001 (2)	0.2425 (2)	0.0400 (6)
H3A	0.3400	0.0403	0.2122	0.048*
N4	0.4966 (3)	−0.0519 (2)	0.3218 (3)	0.0439 (7)
H4A	0.5480	−0.0695	0.3695	0.053*
C1	0.0621 (5)	−0.1393 (4)	0.7813 (4)	0.0604 (10)
H1B	0.1408	−0.1673	0.7127	0.072*
C2	0.0101 (6)	−0.2134 (4)	0.8932 (5)	0.0743 (13)
H2B	0.0531	−0.2919	0.8994	0.089*
C3	−0.1036 (6)	−0.1724 (5)	0.9943 (5)	0.0819 (14)
H3B	−0.1391	−0.2234	1.0691	0.098*
C4	−0.1669 (5)	−0.0552 (5)	0.9864 (4)	0.0759 (13)
H4B	−0.2428	−0.0267	1.0567	0.091*
C5	−0.1177 (4)	0.0195 (4)	0.8750 (4)	0.0577 (10)
H5A	−0.1614	0.0978	0.8695	0.069*
C6	−0.0031 (4)	−0.0226 (3)	0.7712 (3)	0.0496 (9)
C7	0.0582 (4)	0.0508 (3)	0.6474 (3)	0.0497 (9)
C8	0.0013 (4)	0.2288 (3)	0.5134 (3)	0.0466 (8)
C9	0.2023 (4)	0.2824 (3)	0.3077 (3)	0.0415 (8)
C10	0.1586 (4)	0.4028 (3)	0.2774 (4)	0.0526 (9)
H10A	0.0848	0.4461	0.3378	0.063*
C11	0.2265 (4)	0.4562 (3)	0.1565 (4)	0.0530 (9)
C12	0.3378 (5)	0.3993 (3)	0.0662 (4)	0.0594 (10)
H12A	0.3811	0.4381	−0.0147	0.071*
C13	0.3855 (4)	0.2818 (3)	0.0974 (3)	0.0514 (9)
H13A	0.4631	0.2415	0.0371	0.062*
C14	0.3192 (4)	0.2239 (3)	0.2167 (3)	0.0394 (7)
C15	0.4541 (3)	0.0725 (3)	0.3110 (3)	0.0393 (7)
C16	0.4686 (4)	−0.1497 (3)	0.2677 (3)	0.0403 (7)
C17	0.5404 (3)	−0.2712 (3)	0.2888 (3)	0.0392 (7)
C22	0.6633 (4)	−0.2819 (3)	0.3250 (4)	0.0526 (9)
H18A	0.7052	−0.2112	0.3372	0.063*
C21	0.7232 (5)	−0.3984 (4)	0.3429 (4)	0.0673 (11)
H19A	0.8056	−0.4062	0.3675	0.081*
C20	0.6622 (5)	−0.5012 (4)	0.3248 (4)	0.0693 (12)
H20A	0.7035	−0.5791	0.3370	0.083*
C19	0.5408 (5)	−0.4921 (3)	0.2890 (4)	0.0642 (11)
H21A	0.4997	−0.5634	0.2773	0.077*
C18	0.4797 (4)	−0.3769 (3)	0.2702 (3)	0.0488 (8)
H22A	0.3978	−0.3702	0.2450	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1099 (10)	0.0483 (6)	0.0988 (9)	0.0119 (6)	−0.0510 (7)	0.0225 (6)
S1	0.0625 (7)	0.1060 (10)	0.0712 (7)	0.0420 (7)	−0.0088 (6)	0.0230 (7)
S2	0.0667 (6)	0.0323 (4)	0.0726 (6)	0.0039 (4)	−0.0429 (5)	−0.0049 (4)
O1	0.0605 (18)	0.0737 (19)	0.087 (2)	0.0224 (15)	0.0032 (16)	0.0421 (16)
O2	0.0740 (17)	0.0382 (13)	0.0780 (18)	0.0112 (12)	−0.0508 (15)	−0.0109 (12)
N1	0.0401 (15)	0.0577 (18)	0.0452 (16)	0.0099 (13)	−0.0098 (13)	0.0052 (14)
N2	0.0436 (16)	0.0429 (16)	0.0534 (17)	0.0123 (12)	−0.0160 (14)	0.0093 (13)
N3	0.0491 (16)	0.0318 (13)	0.0444 (15)	0.0029 (11)	−0.0241 (13)	−0.0024 (11)
N4	0.0546 (17)	0.0326 (14)	0.0528 (17)	0.0124 (12)	−0.0305 (14)	−0.0064 (12)
C1	0.066 (2)	0.054 (2)	0.065 (2)	−0.0002 (18)	−0.030 (2)	0.0100 (19)
C2	0.091 (3)	0.063 (3)	0.076 (3)	−0.015 (2)	−0.044 (3)	0.026 (2)
C3	0.089 (3)	0.101 (4)	0.060 (3)	−0.031 (3)	−0.038 (3)	0.032 (3)
C4	0.063 (3)	0.112 (4)	0.049 (2)	−0.011 (3)	−0.019 (2)	0.006 (2)
C5	0.051 (2)	0.075 (3)	0.051 (2)	−0.0052 (19)	−0.0231 (18)	0.0013 (19)
C6	0.046 (2)	0.054 (2)	0.054 (2)	−0.0110 (16)	−0.0269 (18)	0.0067 (17)
C7	0.045 (2)	0.046 (2)	0.055 (2)	0.0010 (15)	−0.0170 (17)	0.0080 (16)
C8	0.050 (2)	0.0447 (19)	0.0452 (19)	0.0094 (15)	−0.0195 (16)	−0.0017 (15)
C9	0.0456 (19)	0.0334 (16)	0.0503 (19)	0.0009 (14)	−0.0255 (16)	0.0061 (14)
C10	0.055 (2)	0.0405 (19)	0.064 (2)	0.0103 (16)	−0.0271 (19)	0.0000 (17)
C11	0.066 (2)	0.0375 (18)	0.063 (2)	−0.0026 (17)	−0.037 (2)	0.0152 (17)
C12	0.079 (3)	0.049 (2)	0.051 (2)	−0.0070 (19)	−0.028 (2)	0.0135 (18)
C13	0.064 (2)	0.047 (2)	0.043 (2)	0.0006 (17)	−0.0201 (17)	0.0017 (16)
C14	0.0483 (19)	0.0310 (15)	0.0449 (18)	0.0024 (14)	−0.0254 (15)	0.0014 (14)
C15	0.0402 (17)	0.0361 (17)	0.0398 (17)	0.0047 (13)	−0.0139 (14)	−0.0004 (13)
C16	0.0415 (18)	0.0323 (16)	0.0465 (18)	0.0039 (13)	−0.0158 (15)	−0.0037 (14)
C17	0.0429 (18)	0.0331 (16)	0.0410 (17)	0.0066 (13)	−0.0148 (14)	−0.0059 (13)
C22	0.052 (2)	0.0411 (19)	0.069 (2)	0.0076 (16)	−0.0261 (19)	−0.0121 (17)
C21	0.064 (3)	0.060 (2)	0.087 (3)	0.024 (2)	−0.040 (2)	−0.010 (2)
C20	0.094 (3)	0.036 (2)	0.085 (3)	0.020 (2)	−0.045 (3)	−0.0045 (19)
C19	0.086 (3)	0.0315 (18)	0.081 (3)	0.0004 (18)	−0.039 (2)	−0.0004 (18)
C18	0.053 (2)	0.0397 (18)	0.055 (2)	0.0037 (15)	−0.0214 (17)	−0.0054 (15)

Geometric parameters (Å, º) top

Cl1—C11	1.750 (3)	C4—H4B	0.9300
S1—C8	1.651 (3)	C5—C6	1.385 (5)
S2—C15	1.653 (3)	C5—H5A	0.9300
O1—C7	1.220 (4)	C6—C7	1.482 (5)
O2—C16	1.229 (4)	C9—C14	1.391 (5)
N1—C7	1.363 (4)	C9—C10	1.395 (4)
N1—C8	1.399 (4)	C10—C11	1.375 (5)
N1—H1A	0.8600	C10—H10A	0.9300
N2—C8	1.322 (4)	C11—C12	1.351 (6)
N2—C9	1.409 (4)	C12—C13	1.384 (5)
N2—H2A	0.8600	C12—H12A	0.9300
N3—C15	1.335 (4)	C13—C14	1.376 (5)
N3—C14	1.431 (4)	C13—H13A	0.9300
N3—H3A	0.8600	C16—C17	1.488 (4)
N4—C16	1.361 (4)	C17—C18	1.382 (5)
N4—C15	1.390 (4)	C17—C22	1.384 (5)
N4—H4A	0.8600	C22—C21	1.383 (5)
C1—C2	1.379 (6)	C22—H18A	0.9300
C1—C6	1.390 (5)	C21—C20	1.355 (6)
C1—H1B	0.9300	C21—H19A	0.9300
C2—C3	1.358 (7)	C20—C19	1.367 (6)
C2—H2B	0.9300	C20—H20A	0.9300
C3—C4	1.383 (7)	C19—C18	1.377 (5)
C3—H3B	0.9300	C19—H21A	0.9300
C4—C5	1.376 (6)	C18—H22A	0.9300

C7—N1—C8	129.6 (3)	C11—C10—C9	118.8 (3)
C7—N1—H1A	115.2	C11—C10—H10A	120.6
C8—N1—H1A	115.2	C9—C10—H10A	120.6
C8—N2—C9	130.2 (3)	C12—C11—C10	123.1 (3)
C8—N2—H2A	114.9	C12—C11—Cl1	118.8 (3)
C9—N2—H2A	114.9	C10—C11—Cl1	118.0 (3)
C15—N3—C14	123.5 (3)	C11—C12—C13	118.3 (3)
C15—N3—H3A	118.2	C11—C12—H12A	120.9
C14—N3—H3A	118.2	C13—C12—H12A	120.9
C16—N4—C15	129.3 (3)	C14—C13—C12	120.6 (3)
C16—N4—H4A	115.4	C14—C13—H13A	119.7
C15—N4—H4A	115.4	C12—C13—H13A	119.7
C2—C1—C6	119.9 (4)	C13—C14—C9	120.5 (3)
C2—C1—H1B	120.0	C13—C14—N3	118.5 (3)
C6—C1—H1B	120.0	C9—C14—N3	120.9 (3)
C3—C2—C1	120.3 (4)	N3—C15—N4	115.9 (3)
C3—C2—H2B	119.8	N3—C15—S2	124.3 (2)
C1—C2—H2B	119.8	N4—C15—S2	119.8 (2)
C2—C3—C4	120.2 (4)	O2—C16—N4	121.8 (3)
C2—C3—H3B	119.9	O2—C16—C17	121.5 (3)
C4—C3—H3B	119.9	N4—C16—C17	116.7 (3)
C5—C4—C3	120.3 (4)	C18—C17—C22	119.6 (3)
C5—C4—H4B	119.9	C18—C17—C16	117.3 (3)
C3—C4—H4B	119.9	C22—C17—C16	123.1 (3)
C4—C5—C6	119.7 (4)	C21—C22—C17	119.4 (3)
C4—C5—H5A	120.2	C21—C22—H18A	120.3
C6—C5—H5A	120.2	C17—C22—H18A	120.3
C5—C6—C1	119.5 (4)	C20—C21—C22	120.3 (4)
C5—C6—C7	123.8 (3)	C20—C21—H19A	119.9
C1—C6—C7	116.6 (3)	C22—C21—H19A	119.9
O1—C7—N1	121.0 (3)	C21—C20—C19	120.9 (3)
O1—C7—C6	121.4 (3)	C21—C20—H20A	119.5
N1—C7—C6	117.6 (3)	C19—C20—H20A	119.5
N2—C8—N1	114.9 (3)	C20—C19—C18	119.7 (4)
N2—C8—S1	128.4 (3)	C20—C19—H21A	120.1
N1—C8—S1	116.7 (3)	C18—C19—H21A	120.1
C14—C9—C10	118.6 (3)	C19—C18—C17	120.0 (3)
C14—C9—N2	118.1 (3)	C19—C18—H22A	120.0
C10—C9—N2	123.2 (3)	C17—C18—H22A	120.0

C6—C1—C2—C3	−0.8 (6)	C12—C13—C14—C9	0.4 (5)
C1—C2—C3—C4	−0.9 (7)	C12—C13—C14—N3	177.1 (3)
C2—C3—C4—C5	1.8 (7)	C10—C9—C14—C13	−2.9 (5)
C3—C4—C5—C6	−1.0 (6)	N2—C9—C14—C13	178.9 (3)
C4—C5—C6—C1	−0.7 (5)	C10—C9—C14—N3	−179.5 (3)
C4—C5—C6—C7	−179.7 (3)	N2—C9—C14—N3	2.2 (4)
C2—C1—C6—C5	1.6 (6)	C15—N3—C14—C13	105.1 (4)
C2—C1—C6—C7	−179.4 (4)	C15—N3—C14—C9	−78.2 (4)
C8—N1—C7—O1	0.0 (6)	C14—N3—C15—N4	−177.1 (3)
C8—N1—C7—C6	179.8 (3)	C14—N3—C15—S2	3.7 (4)
C5—C6—C7—O1	159.2 (4)	C16—N4—C15—N3	3.3 (5)
C1—C6—C7—O1	−19.8 (5)	C16—N4—C15—S2	−177.5 (3)
C5—C6—C7—N1	−20.6 (5)	C15—N4—C16—O2	−3.9 (5)
C1—C6—C7—N1	160.4 (3)	C15—N4—C16—C17	175.0 (3)
C9—N2—C8—N1	177.6 (3)	O2—C16—C17—C18	−20.7 (5)
C9—N2—C8—S1	−2.3 (6)	N4—C16—C17—C18	160.4 (3)
C7—N1—C8—N2	−4.2 (5)	O2—C16—C17—C22	159.0 (3)
C7—N1—C8—S1	175.7 (3)	N4—C16—C17—C22	−19.8 (5)
C8—N2—C9—C14	−154.5 (3)	C18—C17—C22—C21	−0.4 (5)
C8—N2—C9—C10	27.3 (6)	C16—C17—C22—C21	179.9 (3)
C14—C9—C10—C11	3.8 (5)	C17—C22—C21—C20	0.2 (6)
N2—C9—C10—C11	−178.1 (3)	C22—C21—C20—C19	−0.1 (7)
C9—C10—C11—C12	−2.4 (6)	C21—C20—C19—C18	0.3 (7)
C9—C10—C11—Cl1	178.2 (3)	C20—C19—C18—C17	−0.6 (6)
C10—C11—C12—C13	−0.1 (6)	C22—C17—C18—C19	0.6 (5)
Cl1—C11—C12—C13	179.3 (3)	C16—C17—C18—C19	−179.6 (3)
C11—C12—C13—C14	1.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S2	0.86	2.86	3.443 (4)	127
N2—H2A···O1	0.86	1.91	2.621 (5)	140
N2—H2A···N3	0.86	2.46	2.791 (4)	103
N3—H3A···O2	0.86	1.96	2.642 (3)	135
C10—H10A···S1	0.93	2.61	3.173 (5)	120
N1—H1A···O2ⁱ	0.86	2.51	3.328 (5)	159
N4—H4A···S2ⁱⁱ	0.86	2.81	3.476 (4)	136

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇ClN₄O₂S₂
M_r	468.97
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.637 (4), 10.820 (4), 11.370 (4)
α, β, γ (°)	84.443 (8), 68.706 (8), 86.551 (9)
V (Å³)	1099.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.49 × 0.16 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.928, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	12132, 4083, 3107
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.173, 1.08
No. of reflections	4083
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S2	0.86	2.86	3.443 (4)	127
N2—H2A···O1	0.86	1.91	2.621 (5)	140
N3—H3A···O2	0.86	1.96	2.642 (3)	135
C10—H10A···S1	0.93	2.61	3.173 (5)	120
N1—H1A···O2ⁱ	0.86	2.51	3.328 (5)	159
N4—H4A···S2ⁱⁱ	0.86	2.81	3.476 (4)	136

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

Acknowledgements

The authors thank the Universiti Kebangsaan Malaysia and the Ministry of Higher Education, Malaysia, for financial support (grant No. UKM-GUP-NBT-08–27–110) and research facilities. Study leave granted to UMO from the Universiti Malaysia Terengganu is very much appreciated.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals 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
Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776. Web of Science CSD CrossRef IUCr Journals Google Scholar
Woei Hung, W. & Kassim, M. B. (2010). Acta Cryst. E66, o3182. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yusof, M. S. M., Ayob, N. A. C., Kadir, M. A. & Yamin, B. M. (2008). Acta Cryst. E64, o937. Web of Science CSD CrossRef IUCr Journals Google Scholar