(±)-1,2-Bis(N′-benzoyl­thio­ureido)cyclo­hexa­ne

Jumal, J.; Ibrahim, A.R.; Yamin, B.M.

doi:10.1107/S1600536811014991

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1256

doi:10.1107/S1600536811014991

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(±)-1,2-Bis(N′-benzoylthioureido)cyclohexane

Juliana Jumal,^a Abdul Razak Ibrahim ^b and Bohari M. Yamin ^c ^*

^aFaculty of Science and Technology, Universiti Sains Islam Malaysia, 71800 Nilai N. Sembilan, Malaysia, ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, USM 11800, Penang, Malaysia, and ^cSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500, Bangi Selangor, Malaysia
^*Correspondence e-mail: bohari@ukm.my

(Received 4 April 2011; accepted 21 April 2011; online 29 April 2011)

In the title compound, C₂₂H₂₄N₄O₂S₂, the two thiourea segments of the side-arm groups are inclined at a dihedral angle of 73.09 (9)°. The central cyclohexane bridge adopts a chair conformation. The molecule is stabilized by N—H⋯O intramolecular hydrogen bonds forming S(6) rings, and N—H⋯O and N—H⋯S intermolecular hydrogen bonds forming infinite chains developing parallel to the b axis.

Related literature

For related structures, see: Yusof et al. (2008 ); Thiam et al. (2008 ). For bond-length data, see Allen et al. (1987 ). For a description of hydrogen-bonding patterns, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₂₄N₄O₂S₂
M_r = 440.57
Monoclinic, C 2/c
a = 19.725 (6) Å
b = 11.054 (3) Å
c = 20.700 (5) Å
β = 91.252 (9)°
V = 4512 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.45 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.891, T_max = 0.950
16892 measured reflections
4212 independent reflections
3334 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.145
S = 1.11
4212 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	2.01	2.677 (3)	134
N3—H3A⋯O2	0.86	1.96	2.645 (3)	136
N1—H1A⋯O2ⁱ	0.86	2.26	3.077 (3)	159
N4—H4A⋯S2ⁱⁱ	0.86	2.56	3.405 (3)	166
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014991/dn2675sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014991/dn2675Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811014991/dn2675Isup3.cml

checkCIF report

Comment top

The title compound, (I) is similar to 1,2-bis[N'-(2,2-dimethylpropionyl) thioureido]cyclohexane (Yusof et al., 2008) except the two side arms are benzoylthioureido (Fig. 1) groups instead of 2,2-dimethylpropionylthioureido.The bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in 1,2-bis[N'-(2,2-dimethylpropionyl)thioureido]cycylohexane and 1,2-bis (N'-benzoylthioureido)benzene (Thiam et al., 2008). However, the dihedral angle between the thiourea groups of 73.09 (9)° is slightly smaller compare to 78.55 (7)° in the propionylthioureido analog.

Both thiourea moieties, S1/N2/C7/C8/C9 and S2/N3/N4/C14/C15 are planar with maximum deviation of 0.017 (3)Å for C9 atom from the least square plane. There are two intramolecular hydrogen bonds N2—H2A..O1 and N3—H3A···O2 forming two pseudo-six membered rings S(6) (Etter et al., 1990; Bernstein et al., 1995) O1···H2A—N2—C8—N1—C7 and O2..H3A—N3—C15—N4—C16 respectively (Table 1). In the crystal structure, the molecules are linked by intermolecular hydrogen bonds N1—H1A···O2 forming a R⁴₂(18) graph set motif and N4—H4A···S2 forming a R²₂(8) motif (Etter et al., 1990; Bernstein et al., 1995). These intermolecular interactions result in the formation of chains extending along the b axis (Fig.2; Table 1).

Related literature top

For related crystal structures, see: Yusof et al. (2008); Thiam et al. (2008). For bond-length data, see Allen et al. (1987). For a description of hydrogen-bonding patterns, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

A solution of benzoylisothiocyanate (3.26 g, 0.02 mol) in 30 ml acetone was added into a flask containing 30 ml acetone solution of 1,2-diamino cyclohexane (1.14 g, 0.01 mol).The mixture was refluxed for 1 h. Then, the solution was filtered-off and left to evaporate at room temperature. The colourless solid was obtained after one day of evaporation(yield 81%, m.p 495.3–497.3 K)

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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Partial packing view of compound ( I ), showing the formation of chains along the b axis built from hydrogen bonds, and the formation of R ⁴₂(18) and R²₂(8) rings. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.[Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1]

(±)-1-Benzoyl-3-[2-(N'-benzoylthioureido)cyclohexyl]thiourea top

Crystal data top

C₂₂H₂₄N₄O₂S₂	F(000) = 1856
M_r = 440.57	D_x = 1.297 Mg m⁻³
Monoclinic, C2/c	Melting point = 495.3–497.3 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 19.725 (6) Å	Cell parameters from 4375 reflections
b = 11.054 (3) Å	θ = 2.0–25.2°
c = 20.700 (5) Å	µ = 0.26 mm⁻¹
β = 91.252 (9)°	T = 298 K
V = 4512 (2) Å³	Block, colourless
Z = 8	0.45 × 0.39 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4212 independent reflections
Radiation source: fine-focus sealed tube	3334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.5°, θ_min = 2.0°
ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→13
T_min = 0.891, T_max = 0.950	l = −24→25
16892 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0596P)² + 4.3773P] where P = (F_o² + 2F_c²)/3
4212 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₂₄N₄O₂S₂	V = 4512 (2) Å³
M_r = 440.57	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.725 (6) Å	µ = 0.26 mm⁻¹
b = 11.054 (3) Å	T = 298 K
c = 20.700 (5) Å	0.45 × 0.39 × 0.20 mm
β = 91.252 (9)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4212 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3334 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.950	R_int = 0.043
16892 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.11	Δρ_max = 0.37 e Å⁻³
4212 reflections	Δρ_min = −0.21 e Å⁻³
272 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	0.02397 (4)	0.38387 (8)	0.42308 (5)	0.0633 (3)
S2	0.02746 (4)	0.92533 (8)	0.41333 (4)	0.0586 (3)
O1	−0.09838 (10)	0.7174 (2)	0.36607 (12)	0.0702 (7)
O2	0.14844 (9)	0.71111 (18)	0.56241 (9)	0.0492 (5)
N1	−0.07970 (10)	0.5330 (2)	0.41058 (11)	0.0468 (6)
H1A	−0.1004	0.4730	0.4279	0.056*
N2	0.02222 (10)	0.6069 (2)	0.37479 (11)	0.0454 (6)
H2A	0.0001	0.6723	0.3664	0.054*
N3	0.12087 (11)	0.7590 (2)	0.43944 (10)	0.0450 (6)
H3A	0.1456	0.7217	0.4678	0.054*
N4	0.08148 (11)	0.86601 (19)	0.52667 (10)	0.0410 (5)
H4A	0.0591	0.9281	0.5394	0.049*
C1	−0.21028 (19)	0.5515 (3)	0.4688 (2)	0.0898 (13)
H1B	−0.1791	0.4990	0.4881	0.108*
C2	−0.2756 (2)	0.5544 (4)	0.4898 (3)	0.124 (2)
H2B	−0.2884	0.5035	0.5231	0.149*
C3	−0.32249 (19)	0.6311 (5)	0.4623 (3)	0.1007 (17)
H3B	−0.3668	0.6324	0.4767	0.121*
C4	−0.3036 (2)	0.7045 (5)	0.4142 (2)	0.1030 (17)
H4B	−0.3352	0.7564	0.3951	0.124*
C5	−0.23709 (17)	0.7038 (4)	0.39271 (18)	0.0871 (13)
H5A	−0.2245	0.7565	0.3601	0.104*
C6	−0.19050 (14)	0.6265 (3)	0.41907 (15)	0.0523 (8)
C7	−0.11937 (14)	0.6315 (3)	0.39623 (14)	0.0477 (7)
C8	−0.01047 (13)	0.5160 (3)	0.40108 (13)	0.0440 (6)
C9	0.09410 (13)	0.6023 (3)	0.35922 (13)	0.0446 (6)
H9A	0.1160	0.5420	0.3874	0.054*
C10	0.10317 (15)	0.5628 (3)	0.28926 (15)	0.0606 (8)
H10A	0.0819	0.4846	0.2825	0.073*
H10B	0.0810	0.6205	0.2605	0.073*
C11	0.17797 (17)	0.5547 (4)	0.27354 (17)	0.0723 (10)
H11A	0.1993	0.4919	0.2997	0.087*
H11B	0.1827	0.5330	0.2285	0.087*
C12	0.21279 (16)	0.6735 (4)	0.28648 (16)	0.0701 (10)
H12A	0.1947	0.7342	0.2570	0.084*
H12B	0.2609	0.6652	0.2786	0.084*
C13	0.20305 (14)	0.7155 (4)	0.35590 (15)	0.0631 (9)
H13A	0.2238	0.7944	0.3619	0.076*
H13B	0.2255	0.6594	0.3853	0.076*
C14	0.12781 (12)	0.7232 (3)	0.37194 (12)	0.0434 (6)
H14A	0.1061	0.7845	0.3442	0.052*
C15	0.07964 (13)	0.8440 (2)	0.46047 (12)	0.0419 (6)
C16	0.11438 (12)	0.8012 (2)	0.57403 (13)	0.0398 (6)
C17	0.10748 (12)	0.8470 (3)	0.64079 (13)	0.0419 (6)
C18	0.10957 (15)	0.9688 (3)	0.65517 (14)	0.0526 (7)
H18A	0.1143	1.0253	0.6223	0.063*
C19	0.10464 (18)	1.0065 (3)	0.71809 (17)	0.0713 (10)
H19A	0.1066	1.0886	0.7278	0.086*
C20	0.09689 (18)	0.9240 (4)	0.76659 (17)	0.0742 (10)
H20A	0.0933	0.9504	0.8090	0.089*
C21	0.09432 (17)	0.8037 (4)	0.75319 (15)	0.0673 (9)
H21A	0.0884	0.7482	0.7863	0.081*
C22	0.10055 (15)	0.7639 (3)	0.69031 (14)	0.0546 (8)
H22A	0.1001	0.6815	0.6813	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0446 (4)	0.0520 (5)	0.0936 (7)	0.0080 (3)	0.0057 (4)	0.0092 (4)
S2	0.0634 (5)	0.0719 (6)	0.0406 (4)	0.0246 (4)	0.0012 (3)	0.0038 (4)
O1	0.0475 (12)	0.0653 (15)	0.0982 (18)	0.0125 (11)	0.0131 (12)	0.0236 (13)
O2	0.0491 (11)	0.0522 (12)	0.0463 (11)	0.0115 (9)	−0.0001 (9)	−0.0018 (9)
N1	0.0325 (11)	0.0479 (13)	0.0602 (15)	0.0014 (10)	0.0076 (10)	0.0023 (11)
N2	0.0320 (11)	0.0500 (13)	0.0544 (14)	0.0050 (10)	0.0054 (10)	0.0016 (11)
N3	0.0399 (12)	0.0545 (14)	0.0405 (13)	0.0060 (11)	0.0009 (10)	−0.0002 (11)
N4	0.0438 (12)	0.0408 (12)	0.0387 (12)	0.0064 (10)	0.0041 (9)	0.0007 (10)
C1	0.067 (2)	0.060 (2)	0.144 (4)	0.0126 (18)	0.050 (2)	0.012 (2)
C2	0.086 (3)	0.073 (3)	0.217 (6)	0.002 (2)	0.090 (4)	0.002 (3)
C3	0.045 (2)	0.112 (4)	0.147 (5)	−0.008 (2)	0.030 (2)	−0.065 (3)
C4	0.051 (2)	0.175 (5)	0.083 (3)	0.042 (3)	−0.009 (2)	−0.032 (3)
C5	0.053 (2)	0.141 (4)	0.067 (2)	0.036 (2)	0.0017 (17)	0.002 (2)
C6	0.0376 (15)	0.0555 (18)	0.064 (2)	0.0017 (13)	0.0041 (13)	−0.0204 (15)
C7	0.0389 (14)	0.0502 (18)	0.0541 (18)	0.0014 (13)	0.0022 (13)	−0.0044 (14)
C8	0.0365 (13)	0.0499 (16)	0.0456 (16)	0.0021 (12)	0.0004 (11)	−0.0064 (13)
C9	0.0335 (13)	0.0547 (17)	0.0459 (16)	0.0058 (12)	0.0061 (11)	−0.0004 (13)
C10	0.0539 (18)	0.072 (2)	0.0557 (19)	0.0005 (16)	0.0075 (14)	−0.0163 (16)
C11	0.060 (2)	0.100 (3)	0.057 (2)	0.018 (2)	0.0176 (16)	−0.0145 (19)
C12	0.0414 (16)	0.111 (3)	0.059 (2)	0.0034 (18)	0.0204 (14)	−0.005 (2)
C13	0.0391 (16)	0.093 (3)	0.0574 (19)	−0.0060 (16)	0.0096 (13)	−0.0071 (18)
C14	0.0352 (13)	0.0594 (18)	0.0358 (14)	0.0029 (12)	0.0063 (11)	−0.0006 (13)
C15	0.0370 (13)	0.0480 (16)	0.0411 (15)	−0.0013 (12)	0.0077 (11)	0.0026 (13)
C16	0.0327 (13)	0.0414 (15)	0.0453 (15)	−0.0023 (11)	0.0028 (11)	0.0035 (12)
C17	0.0343 (13)	0.0500 (16)	0.0413 (15)	0.0019 (12)	−0.0009 (11)	0.0017 (13)
C18	0.0573 (17)	0.0518 (18)	0.0485 (17)	0.0038 (14)	−0.0049 (13)	−0.0018 (14)
C19	0.089 (3)	0.064 (2)	0.061 (2)	0.0148 (19)	−0.0099 (18)	−0.0170 (18)
C20	0.082 (2)	0.096 (3)	0.0451 (19)	0.016 (2)	0.0042 (17)	−0.018 (2)
C21	0.073 (2)	0.088 (3)	0.0418 (18)	−0.0025 (19)	0.0034 (15)	0.0087 (17)
C22	0.0590 (18)	0.0589 (19)	0.0457 (17)	−0.0045 (15)	−0.0003 (14)	0.0005 (15)

Geometric parameters (Å, º) top

S1—C8	1.670 (3)	C9—C14	1.513 (4)
S2—C15	1.666 (3)	C9—C10	1.527 (4)
O1—C7	1.215 (3)	C9—H9A	0.9800
O2—C16	1.228 (3)	C10—C11	1.521 (4)
N1—C7	1.370 (4)	C10—H10A	0.9700
N1—C8	1.397 (3)	C10—H10B	0.9700
N1—H1A	0.8600	C11—C12	1.504 (5)
N2—C8	1.318 (3)	C11—H11A	0.9700
N2—C9	1.462 (3)	C11—H11B	0.9700
N2—H2A	0.8600	C12—C13	1.526 (4)
N3—C15	1.323 (3)	C12—H12A	0.9700
N3—C14	1.462 (3)	C12—H12B	0.9700
N3—H3A	0.8600	C13—C14	1.530 (4)
N4—C16	1.366 (3)	C13—H13A	0.9700
N4—C15	1.392 (3)	C13—H13B	0.9700
N4—H4A	0.8600	C14—H14A	0.9800
C1—C2	1.369 (5)	C16—C17	1.481 (4)
C1—C6	1.385 (5)	C17—C18	1.379 (4)
C1—H1B	0.9300	C17—C22	1.386 (4)
C2—C3	1.369 (7)	C18—C19	1.373 (4)
C2—H2B	0.9300	C18—H18A	0.9300
C3—C4	1.342 (7)	C19—C20	1.367 (5)
C3—H3B	0.9300	C19—H19A	0.9300
C4—C5	1.394 (5)	C20—C21	1.359 (5)
C4—H4B	0.9300	C20—H20A	0.9300
C5—C6	1.360 (5)	C21—C22	1.382 (4)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.491 (4)	C22—H22A	0.9300

C7—N1—C8	129.2 (2)	C12—C11—C10	110.6 (3)
C7—N1—H1A	115.4	C12—C11—H11A	109.5
C8—N1—H1A	115.4	C10—C11—H11A	109.5
C8—N2—C9	123.4 (2)	C12—C11—H11B	109.5
C8—N2—H2A	118.3	C10—C11—H11B	109.5
C9—N2—H2A	118.3	H11A—C11—H11B	108.1
C15—N3—C14	125.3 (2)	C11—C12—C13	111.5 (3)
C15—N3—H3A	117.4	C11—C12—H12A	109.3
C14—N3—H3A	117.4	C13—C12—H12A	109.3
C16—N4—C15	128.1 (2)	C11—C12—H12B	109.3
C16—N4—H4A	116.0	C13—C12—H12B	109.3
C15—N4—H4A	116.0	H12A—C12—H12B	108.0
C2—C1—C6	120.2 (4)	C12—C13—C14	111.3 (2)
C2—C1—H1B	119.9	C12—C13—H13A	109.4
C6—C1—H1B	119.9	C14—C13—H13A	109.4
C1—C2—C3	121.0 (5)	C12—C13—H13B	109.4
C1—C2—H2B	119.5	C14—C13—H13B	109.4
C3—C2—H2B	119.5	H13A—C13—H13B	108.0
C4—C3—C2	119.1 (4)	N3—C14—C9	110.8 (2)
C4—C3—H3B	120.5	N3—C14—C13	109.5 (2)
C2—C3—H3B	120.5	C9—C14—C13	109.8 (2)
C3—C4—C5	120.8 (4)	N3—C14—H14A	108.9
C3—C4—H4B	119.6	C9—C14—H14A	108.9
C5—C4—H4B	119.6	C13—C14—H14A	108.9
C6—C5—C4	120.5 (4)	N3—C15—N4	116.4 (2)
C6—C5—H5A	119.8	N3—C15—S2	124.6 (2)
C4—C5—H5A	119.8	N4—C15—S2	119.00 (19)
C5—C6—C1	118.4 (3)	O2—C16—N4	122.5 (2)
C5—C6—C7	118.8 (3)	O2—C16—C17	121.5 (2)
C1—C6—C7	122.7 (3)	N4—C16—C17	116.0 (2)
O1—C7—N1	122.3 (3)	C18—C17—C22	119.4 (3)
O1—C7—C6	121.7 (3)	C18—C17—C16	122.2 (3)
N1—C7—C6	116.0 (3)	C22—C17—C16	118.4 (3)
N2—C8—N1	116.4 (2)	C19—C18—C17	119.9 (3)
N2—C8—S1	125.4 (2)	C19—C18—H18A	120.0
N1—C8—S1	118.2 (2)	C17—C18—H18A	120.0
N2—C9—C14	110.8 (2)	C20—C19—C18	120.4 (3)
N2—C9—C10	110.7 (2)	C20—C19—H19A	119.8
C14—C9—C10	110.9 (2)	C18—C19—H19A	119.8
N2—C9—H9A	108.1	C21—C20—C19	120.4 (3)
C14—C9—H9A	108.1	C21—C20—H20A	119.8
C10—C9—H9A	108.1	C19—C20—H20A	119.8
C11—C10—C9	110.8 (2)	C20—C21—C22	120.0 (3)
C11—C10—H10A	109.5	C20—C21—H21A	120.0
C9—C10—H10A	109.5	C22—C21—H21A	120.0
C11—C10—H10B	109.5	C21—C22—C17	119.8 (3)
C9—C10—H10B	109.5	C21—C22—H22A	120.1
H10A—C10—H10B	108.1	C17—C22—H22A	120.1

C6—C1—C2—C3	−0.2 (7)	C15—N3—C14—C13	132.9 (3)
C1—C2—C3—C4	−0.2 (8)	N2—C9—C14—N3	58.4 (3)
C2—C3—C4—C5	−0.5 (7)	C10—C9—C14—N3	−178.2 (2)
C3—C4—C5—C6	1.5 (7)	N2—C9—C14—C13	179.4 (2)
C4—C5—C6—C1	−1.8 (6)	C10—C9—C14—C13	−57.2 (3)
C4—C5—C6—C7	−178.0 (4)	C12—C13—C14—N3	177.7 (3)
C2—C1—C6—C5	1.2 (6)	C12—C13—C14—C9	55.9 (4)
C2—C1—C6—C7	177.2 (4)	C14—N3—C15—N4	−178.8 (2)
C8—N1—C7—O1	7.3 (5)	C14—N3—C15—S2	0.5 (4)
C8—N1—C7—C6	−173.5 (3)	C16—N4—C15—N3	−8.8 (4)
C5—C6—C7—O1	16.3 (5)	C16—N4—C15—S2	171.9 (2)
C1—C6—C7—O1	−159.7 (3)	C15—N4—C16—O2	0.5 (4)
C5—C6—C7—N1	−162.9 (3)	C15—N4—C16—C17	179.7 (2)
C1—C6—C7—N1	21.1 (4)	O2—C16—C17—C18	138.7 (3)
C9—N2—C8—N1	−177.5 (2)	N4—C16—C17—C18	−40.5 (3)
C9—N2—C8—S1	2.1 (4)	O2—C16—C17—C22	−39.6 (4)
C7—N1—C8—N2	0.2 (4)	N4—C16—C17—C22	141.3 (3)
C7—N1—C8—S1	−179.4 (2)	C22—C17—C18—C19	−0.1 (4)
C8—N2—C9—C14	−143.0 (3)	C16—C17—C18—C19	−178.4 (3)
C8—N2—C9—C10	93.5 (3)	C17—C18—C19—C20	−0.7 (5)
N2—C9—C10—C11	−178.4 (3)	C18—C19—C20—C21	0.3 (5)
C14—C9—C10—C11	58.1 (4)	C19—C20—C21—C22	0.9 (5)
C9—C10—C11—C12	−56.7 (4)	C20—C21—C22—C17	−1.8 (5)
C10—C11—C12—C13	55.7 (4)	C18—C17—C22—C21	1.4 (4)
C11—C12—C13—C14	−55.7 (4)	C16—C17—C22—C21	179.7 (3)
C15—N3—C14—C9	−105.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	2.01	2.677 (3)	134
N3—H3A···O2	0.86	1.96	2.645 (3)	136
N1—H1A···O2ⁱ	0.86	2.26	3.077 (3)	159
N4—H4A···S2ⁱⁱ	0.86	2.56	3.405 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₄O₂S₂
M_r	440.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	19.725 (6), 11.054 (3), 20.700 (5)
β (°)	91.252 (9)
V (Å³)	4512 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.45 × 0.39 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.891, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	16892, 4212, 3334
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.145, 1.11
No. of reflections	4212
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), 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···O1	0.86	2.01	2.677 (3)	134
N3—H3A···O2	0.86	1.96	2.645 (3)	136
N1—H1A···O2ⁱ	0.86	2.26	3.077 (3)	159
N4—H4A···S2ⁱⁱ	0.86	2.56	3.405 (3)	166

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

Acknowledgements

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, Universiti Sains Islam Malaysia and the Ministry of Higher Education, Malaysia for research grants Nos. UKM-GUP-NBT-08-27-110 and USIM-FST-FRGS-05-50209.

References

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