1-(4-Methyl­benzo­yl)-3-{2-[3-(4-methyl­benzo­yl)thio­ureido]phen­yl}thio­urea

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

doi:10.1107/S1600536811035586

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2583

https://doi.org/10.1107/S1600536811035586

Open

access

1-(4-Methylbenzoyl)-3-{2-[3-(4-methylbenzoyl)thioureido]phenyl}thiourea

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

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

(Received 26 August 2011; accepted 1 September 2011; online 14 September 2011)

In the title compound, C₂₄H₂₂N₄O₂S₂, the dihedral angles formed by the thioureido groups with the attached benzene ring are 43.81 (13) and 75.25 (13)°. The dihedral angle between the thioureido groups is 85.48 (10)°. The molecule is stabilized by intramolecular N—H⋯S, N—H⋯O and C—H⋯S hydrogen bonds. In the crystal, molecules are linked by intermolecular N—H⋯S hydrogen bonds together with C—H⋯π interactions.

Related literature

For the structure of related bis-carbomothioyl thioureas, see: Yamin & Osman (2011 ); Thiam et al. (2008 ).

Experimental

Crystal data

C₂₄H₂₂N₄O₂S₂
M_r = 462.58
Triclinic, $[P \overline 1]$
a = 7.1565 (18) Å
b = 11.394 (3) Å
c = 14.332 (4) Å
α = 96.414 (5)°
β = 99.066 (6)°
γ = 94.085 (6)°
V = 1142.1 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.50 × 0.12 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.880, T_max = 0.984
13125 measured reflections
4472 independent reflections
2810 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.143
S = 1.02
4472 reflections
294 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2	0.86	2.83	3.476 (3)	134
N1—H1⋯O1	0.86	1.95	2.651 (3)	138
N3—H3⋯O2	0.86	1.97	2.640 (3)	134
C2—H2A⋯S1	0.93	2.79	3.223 (3)	110
N4—H4⋯S2ⁱ	0.86	2.71	3.533 (3)	161
C15—H15B⋯Cg1ⁱⁱ	0.96	2.76	3.509 (4)	136
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -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: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035586/rz2633sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035586/rz2633Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035586/rz2633Isup3.cml

checkCIF report

Comment top

The title compound, 1,2-bis(N'-4-methylbenzoylthioureido)benzene (systematic name: 1-(4-methylbenzoyl)-3-{2-[3-(4-methylbenzoyl)thioureido]phenyl}thiourea), is similar to 1,2-bis(N'-benzoylthioureido)benzene (Thiam et al., 2008) except for the presence of methyl groups at para position of the benzoyl group (Fig. 1). Both thioureido groups S1/N1/N2/C7/C1 and S2/N3/N4/C16/C6 are planar with maximum deviation from the least square planes of 0.033 (2)Å for the N1 atom. The thioureido groups form dihedral angles of 43.81 (13) and 75.25 (13) Å, respectively, with the central benzene ring. The dihedral between the two thioureido groups is 85.58 (10)°. There are four intramolecular hydrogen bonds forming three six-membered ring [O1···H1—N1—C7—N2—C8], [O2···H3A—N3—C16—N4—C17] and [H2A···S1—C7—N1—C1—C2], and one seven-membered ring [H1···S2—C16—N3—C6—C1—N1] as compared to two intramolecular hydrogen bonds observed in 1,2-bis(N'-benzoylthioureido) benzene. The introduction of chloro atom to the bridging benzene ring in 1,2-bis(N'-benzoylthioureido)-4-chlorobenzene (Yamin & Osman, 2011) allowed four intramolecular hydrogen bonds. In the crystal structure, the molecules are linked by N1—H1A···S1 intermolecular hydrogen bonds (symmetry codes as in Table 1) to form centrosymmetric dimers (Fig. 2). In addition, a C—H···π interaction with distance of 2.760Å and an angle of 136° is also present.

Related literature top

For the structure of related bis-carbomothioyl thioureas, see: Yamin & Osman (2011); Thiam et al. (2008).

Experimental top

To a stirred acetone solution (75 ml) of para-benzoyl chloride (0.04 mol) and ammonium thiocyanate (0.04 mol) 1,2-phenylenediamine (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 formed was filtered off, washed with distilled water and cold ethanol and then dried under vacuum. Good quality crystals were obtained by recrystallization from ethanol.

Structure description top

For the structure of related bis-carbomothioyl thioureas, see: Yamin & Osman (2011); Thiam et al. (2008).

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. Intermolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing diagram of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

1-(4-Methylbenzoyl)-3-{2-[3-(4-methylbenzoyl)thioureido]phenyl}thiourea top

Crystal data top

C₂₄H₂₂N₄O₂S₂	Z = 2
M_r = 462.58	F(000) = 484
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Melting point = 475.4–476.6 K
a = 7.1565 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.394 (3) Å	Cell parameters from 1550 reflections
c = 14.332 (4) Å	θ = 1.8–26.0°
α = 96.414 (5)°	µ = 0.26 mm⁻¹
β = 99.066 (6)°	T = 298 K
γ = 94.085 (6)°	Slab, colourless
V = 1142.1 (5) Å³	0.50 × 0.12 × 0.06 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4472 independent reflections
Radiation source: fine-focus sealed tube	2810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 83.66 pixels mm^-1	θ_max = 26.0°, θ_min = 1.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −14→14
T_min = 0.880, T_max = 0.984	l = −17→17
13125 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0601P)² + 0.1876P] where P = (F_o² + 2F_c²)/3
4472 reflections	(Δ/σ)_max < 0.001
294 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₄H₂₂N₄O₂S₂	γ = 94.085 (6)°
M_r = 462.58	V = 1142.1 (5) Å³
Triclinic, P1	Z = 2
a = 7.1565 (18) Å	Mo Kα radiation
b = 11.394 (3) Å	µ = 0.26 mm⁻¹
c = 14.332 (4) Å	T = 298 K
α = 96.414 (5)°	0.50 × 0.12 × 0.06 mm
β = 99.066 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4472 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2810 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.984	R_int = 0.053
13125 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.32 e Å⁻³
4472 reflections	Δρ_min = −0.19 e Å⁻³
294 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	1.23642 (15)	1.02145 (9)	0.41453 (8)	0.0810 (4)
S2	1.21023 (12)	0.60423 (7)	0.10031 (6)	0.0488 (3)
O1	0.9229 (3)	0.6795 (2)	0.25909 (17)	0.0661 (7)
O2	0.9013 (3)	0.87729 (19)	−0.05615 (16)	0.0638 (7)
N1	1.2155 (3)	0.8412 (2)	0.27623 (17)	0.0438 (6)
H1	1.1524	0.7764	0.2483	0.053*
N2	1.0044 (4)	0.8279 (2)	0.38102 (18)	0.0457 (6)
H2	0.968 (4)	0.868 (2)	0.4283 (14)	0.055*
N3	1.1759 (3)	0.8295 (2)	0.07633 (17)	0.0467 (6)
H3	1.1088	0.8820	0.0526	0.056*
N4	0.9377 (3)	0.6947 (2)	−0.00916 (17)	0.0447 (6)
H4	0.8882	0.6224	−0.0191	0.054*
C1	1.3716 (4)	0.8820 (2)	0.2346 (2)	0.0403 (7)
C2	1.5444 (4)	0.9285 (3)	0.2888 (2)	0.0489 (8)
H2A	1.5595	0.9358	0.3549	0.059*
C3	1.6929 (5)	0.9638 (3)	0.2455 (3)	0.0566 (9)
H3A	1.8068	0.9970	0.2826	0.068*
C4	1.6755 (5)	0.9508 (3)	0.1478 (3)	0.0598 (9)
H4A	1.7777	0.9736	0.1190	0.072*
C5	1.5054 (5)	0.9036 (3)	0.0931 (2)	0.0534 (8)
H5	1.4926	0.8943	0.0270	0.064*
C6	1.3535 (4)	0.8699 (2)	0.1363 (2)	0.0418 (7)
C7	1.1550 (4)	0.8911 (3)	0.3530 (2)	0.0456 (8)
C8	0.8930 (4)	0.7289 (3)	0.3340 (2)	0.0454 (8)
C9	0.7318 (4)	0.6900 (2)	0.3800 (2)	0.0416 (7)
C10	0.5718 (4)	0.6305 (3)	0.3223 (2)	0.0509 (8)
H10	0.5712	0.6124	0.2573	0.061*
C11	0.4137 (5)	0.5981 (3)	0.3605 (2)	0.0557 (9)
H11	0.3079	0.5575	0.3209	0.067*
C12	0.4092 (4)	0.6245 (3)	0.4563 (2)	0.0475 (8)
C13	0.5708 (5)	0.6804 (3)	0.5143 (2)	0.0541 (9)
H13	0.5722	0.6965	0.5795	0.065*
C14	0.7305 (4)	0.7125 (3)	0.4766 (2)	0.0492 (8)
H14	0.8382	0.7498	0.5167	0.059*
C15	0.2339 (5)	0.5942 (3)	0.4979 (3)	0.0646 (10)
H15A	0.1803	0.6658	0.5178	0.097*
H15B	0.2671	0.5523	0.5517	0.097*
H15C	0.1425	0.5452	0.4506	0.097*
C16	1.1071 (4)	0.7164 (3)	0.05479 (19)	0.0409 (7)
C17	0.8385 (5)	0.7739 (3)	−0.0587 (2)	0.0466 (8)
C18	0.6482 (4)	0.7287 (3)	−0.1130 (2)	0.0442 (7)
C19	0.5775 (5)	0.7814 (3)	−0.1920 (2)	0.0528 (9)
H19	0.6531	0.8397	−0.2126	0.063*
C20	0.3966 (5)	0.7482 (3)	−0.2401 (2)	0.0578 (9)
H20	0.3527	0.7835	−0.2939	0.069*
C21	0.2779 (5)	0.6637 (3)	−0.2106 (2)	0.0513 (8)
C22	0.3506 (5)	0.6101 (3)	−0.1326 (2)	0.0547 (9)
H22	0.2750	0.5515	−0.1123	0.066*
C23	0.5325 (5)	0.6415 (3)	−0.0843 (2)	0.0503 (8)
H23	0.5782	0.6039	−0.0320	0.060*
C24	0.0761 (5)	0.6314 (4)	−0.2600 (3)	0.0761 (11)
H24A	0.0074	0.5885	−0.2203	0.114*
H24B	0.0755	0.5828	−0.3193	0.114*
H24C	0.0167	0.7024	−0.2721	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0742 (7)	0.0602 (6)	0.1025 (8)	−0.0252 (5)	0.0373 (6)	−0.0290 (6)
S2	0.0552 (5)	0.0405 (5)	0.0473 (5)	0.0033 (4)	−0.0002 (4)	0.0039 (4)
O1	0.0648 (16)	0.0619 (15)	0.0678 (16)	−0.0208 (12)	0.0280 (13)	−0.0159 (13)
O2	0.0678 (16)	0.0420 (13)	0.0732 (16)	−0.0071 (12)	−0.0106 (13)	0.0107 (11)
N1	0.0438 (15)	0.0411 (14)	0.0438 (15)	−0.0100 (12)	0.0060 (12)	0.0034 (12)
N2	0.0462 (16)	0.0428 (15)	0.0469 (16)	−0.0064 (12)	0.0118 (13)	0.0008 (12)
N3	0.0494 (16)	0.0390 (15)	0.0488 (16)	−0.0002 (12)	0.0002 (13)	0.0070 (12)
N4	0.0502 (16)	0.0328 (13)	0.0467 (15)	−0.0025 (12)	−0.0009 (13)	0.0022 (11)
C1	0.0391 (18)	0.0312 (15)	0.0496 (19)	−0.0006 (13)	0.0049 (15)	0.0065 (13)
C2	0.0435 (19)	0.0444 (18)	0.055 (2)	−0.0012 (15)	−0.0011 (16)	0.0055 (15)
C3	0.0372 (19)	0.0426 (19)	0.088 (3)	0.0026 (15)	0.0047 (19)	0.0097 (18)
C4	0.046 (2)	0.054 (2)	0.085 (3)	0.0001 (17)	0.026 (2)	0.0114 (19)
C5	0.058 (2)	0.0463 (19)	0.059 (2)	0.0030 (17)	0.0173 (18)	0.0077 (16)
C6	0.0395 (18)	0.0321 (16)	0.052 (2)	−0.0014 (13)	0.0055 (15)	0.0043 (14)
C7	0.0423 (18)	0.0441 (18)	0.049 (2)	−0.0020 (15)	0.0043 (15)	0.0058 (15)
C8	0.0479 (19)	0.0369 (17)	0.050 (2)	0.0011 (15)	0.0086 (16)	0.0014 (15)
C9	0.0405 (18)	0.0346 (16)	0.0495 (19)	0.0004 (14)	0.0083 (15)	0.0059 (14)
C10	0.053 (2)	0.0518 (19)	0.0471 (19)	−0.0055 (16)	0.0095 (17)	0.0091 (15)
C11	0.046 (2)	0.059 (2)	0.058 (2)	−0.0091 (17)	0.0009 (17)	0.0098 (17)
C12	0.0408 (19)	0.0436 (18)	0.062 (2)	0.0070 (15)	0.0136 (16)	0.0132 (16)
C13	0.057 (2)	0.056 (2)	0.051 (2)	−0.0006 (17)	0.0200 (18)	0.0030 (16)
C14	0.0460 (19)	0.0492 (19)	0.049 (2)	−0.0034 (15)	0.0070 (16)	−0.0034 (15)
C15	0.050 (2)	0.072 (2)	0.078 (3)	0.0047 (18)	0.0217 (19)	0.022 (2)
C16	0.0430 (18)	0.0446 (18)	0.0347 (17)	−0.0015 (14)	0.0105 (14)	0.0012 (14)
C17	0.054 (2)	0.0427 (19)	0.0406 (18)	0.0033 (16)	0.0030 (15)	0.0030 (15)
C18	0.0486 (19)	0.0390 (17)	0.0423 (18)	0.0040 (15)	0.0038 (15)	−0.0015 (14)
C19	0.065 (2)	0.0398 (18)	0.050 (2)	−0.0036 (16)	0.0046 (18)	0.0063 (15)
C20	0.068 (2)	0.049 (2)	0.051 (2)	0.0066 (18)	−0.0066 (18)	0.0041 (16)
C21	0.050 (2)	0.054 (2)	0.046 (2)	0.0082 (17)	0.0033 (16)	−0.0092 (16)
C22	0.052 (2)	0.060 (2)	0.052 (2)	−0.0020 (17)	0.0153 (17)	0.0035 (17)
C23	0.050 (2)	0.056 (2)	0.0448 (19)	0.0074 (17)	0.0068 (16)	0.0087 (15)
C24	0.059 (2)	0.101 (3)	0.063 (2)	0.002 (2)	0.0022 (19)	−0.001 (2)

Geometric parameters (Å, º) top

S1—C7	1.656 (3)	C9—C10	1.386 (4)
S2—C16	1.665 (3)	C10—C11	1.378 (4)
O1—C8	1.213 (3)	C10—H10	0.9300
O2—C17	1.225 (3)	C11—C12	1.377 (4)
N1—C7	1.329 (4)	C11—H11	0.9300
N1—C1	1.421 (4)	C12—C13	1.382 (4)
N1—H1	0.8600	C12—C15	1.506 (4)
N2—C8	1.377 (4)	C13—C14	1.383 (4)
N2—C7	1.390 (4)	C13—H13	0.9300
N2—H2	0.859 (10)	C14—H14	0.9300
N3—C16	1.331 (3)	C15—H15A	0.9600
N3—C6	1.432 (4)	C15—H15B	0.9600
N3—H3	0.8600	C15—H15C	0.9600
N4—C17	1.378 (4)	C17—C18	1.484 (4)
N4—C16	1.389 (4)	C18—C19	1.382 (4)
N4—H4	0.8600	C18—C23	1.387 (4)
C1—C6	1.385 (4)	C19—C20	1.373 (4)
C1—C2	1.387 (4)	C19—H19	0.9300
C2—C3	1.371 (4)	C20—C21	1.384 (5)
C2—H2A	0.9300	C20—H20	0.9300
C3—C4	1.376 (5)	C21—C22	1.380 (4)
C3—H3A	0.9300	C21—C24	1.506 (4)
C4—C5	1.378 (4)	C22—C23	1.378 (4)
C4—H4A	0.9300	C22—H22	0.9300
C5—C6	1.385 (4)	C23—H23	0.9300
C5—H5	0.9300	C24—H24A	0.9600
C8—C9	1.481 (4)	C24—H24B	0.9600
C9—C14	1.381 (4)	C24—H24C	0.9600

C7—N1—C1	127.9 (2)	C11—C12—C13	118.3 (3)
C7—N1—H1	116.1	C11—C12—C15	121.6 (3)
C1—N1—H1	116.1	C13—C12—C15	120.1 (3)
C8—N2—C7	129.1 (3)	C12—C13—C14	120.7 (3)
C8—N2—H2	120 (2)	C12—C13—H13	119.6
C7—N2—H2	110 (2)	C14—C13—H13	119.6
C16—N3—C6	124.7 (3)	C9—C14—C13	120.8 (3)
C16—N3—H3	117.7	C9—C14—H14	119.6
C6—N3—H3	117.7	C13—C14—H14	119.6
C17—N4—C16	128.4 (3)	C12—C15—H15A	109.5
C17—N4—H4	115.8	C12—C15—H15B	109.5
C16—N4—H4	115.8	H15A—C15—H15B	109.5
C6—C1—C2	118.8 (3)	C12—C15—H15C	109.5
C6—C1—N1	118.7 (3)	H15A—C15—H15C	109.5
C2—C1—N1	122.4 (3)	H15B—C15—H15C	109.5
C3—C2—C1	120.4 (3)	N3—C16—N4	115.9 (3)
C3—C2—H2A	119.8	N3—C16—S2	124.1 (2)
C1—C2—H2A	119.8	N4—C16—S2	120.0 (2)
C2—C3—C4	120.8 (3)	O2—C17—N4	121.9 (3)
C2—C3—H3A	119.6	O2—C17—C18	121.5 (3)
C4—C3—H3A	119.6	N4—C17—C18	116.6 (3)
C3—C4—C5	119.4 (3)	C19—C18—C23	118.4 (3)
C3—C4—H4A	120.3	C19—C18—C17	118.6 (3)
C5—C4—H4A	120.3	C23—C18—C17	122.8 (3)
C4—C5—C6	120.1 (3)	C20—C19—C18	120.5 (3)
C4—C5—H5	119.9	C20—C19—H19	119.7
C6—C5—H5	119.9	C18—C19—H19	119.7
C5—C6—C1	120.4 (3)	C19—C20—C21	121.6 (3)
C5—C6—N3	117.9 (3)	C19—C20—H20	119.2
C1—C6—N3	121.5 (3)	C21—C20—H20	119.2
N1—C7—N2	115.5 (3)	C22—C21—C20	117.5 (3)
N1—C7—S1	126.3 (2)	C22—C21—C24	120.6 (3)
N2—C7—S1	118.1 (2)	C20—C21—C24	121.9 (3)
O1—C8—N2	121.9 (3)	C23—C22—C21	121.5 (3)
O1—C8—C9	122.9 (3)	C23—C22—H22	119.3
N2—C8—C9	115.2 (3)	C21—C22—H22	119.3
C14—C9—C10	118.4 (3)	C22—C23—C18	120.4 (3)
C14—C9—C8	123.6 (3)	C22—C23—H23	119.8
C10—C9—C8	117.9 (3)	C18—C23—H23	119.8
C11—C10—C9	120.4 (3)	C21—C24—H24A	109.5
C11—C10—H10	119.8	C21—C24—H24B	109.5
C9—C10—H10	119.8	H24A—C24—H24B	109.5
C12—C11—C10	121.3 (3)	C21—C24—H24C	109.5
C12—C11—H11	119.3	H24A—C24—H24C	109.5
C10—C11—H11	119.3	H24B—C24—H24C	109.5

C7—N1—C1—C6	−141.4 (3)	C10—C11—C12—C13	−2.6 (5)
C7—N1—C1—C2	41.6 (4)	C10—C11—C12—C15	177.2 (3)
C6—C1—C2—C3	1.3 (4)	C11—C12—C13—C14	2.2 (5)
N1—C1—C2—C3	178.2 (3)	C15—C12—C13—C14	−177.6 (3)
C1—C2—C3—C4	−1.9 (5)	C10—C9—C14—C13	−2.3 (4)
C2—C3—C4—C5	1.1 (5)	C8—C9—C14—C13	175.9 (3)
C3—C4—C5—C6	0.1 (5)	C12—C13—C14—C9	0.3 (5)
C4—C5—C6—C1	−0.7 (5)	C6—N3—C16—N4	−176.2 (3)
C4—C5—C6—N3	175.5 (3)	C6—N3—C16—S2	4.4 (4)
C2—C1—C6—C5	0.0 (4)	C17—N4—C16—N3	5.3 (4)
N1—C1—C6—C5	−177.0 (3)	C17—N4—C16—S2	−175.3 (2)
C2—C1—C6—N3	−176.1 (3)	C16—N4—C17—O2	5.6 (5)
N1—C1—C6—N3	6.9 (4)	C16—N4—C17—C18	−172.4 (3)
C16—N3—C6—C5	103.2 (3)	O2—C17—C18—C19	28.5 (5)
C16—N3—C6—C1	−80.6 (4)	N4—C17—C18—C19	−153.4 (3)
C1—N1—C7—N2	−176.4 (3)	O2—C17—C18—C23	−146.9 (3)
C1—N1—C7—S1	5.9 (5)	N4—C17—C18—C23	31.1 (4)
C8—N2—C7—N1	−9.3 (5)	C23—C18—C19—C20	0.4 (5)
C8—N2—C7—S1	168.5 (3)	C17—C18—C19—C20	−175.2 (3)
C7—N2—C8—O1	3.7 (5)	C18—C19—C20—C21	1.4 (5)
C7—N2—C8—C9	−174.4 (3)	C19—C20—C21—C22	−2.4 (5)
O1—C8—C9—C14	155.4 (3)	C19—C20—C21—C24	176.8 (3)
N2—C8—C9—C14	−26.5 (4)	C20—C21—C22—C23	1.7 (5)
O1—C8—C9—C10	−26.4 (4)	C24—C21—C22—C23	−177.6 (3)
N2—C8—C9—C10	151.7 (3)	C21—C22—C23—C18	0.1 (5)
C14—C9—C10—C11	1.9 (5)	C19—C18—C23—C22	−1.1 (5)
C8—C9—C10—C11	−176.4 (3)	C17—C18—C23—C22	174.3 (3)
C9—C10—C11—C12	0.6 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.86	2.83	3.476 (3)	134
N1—H1···O1	0.86	1.95	2.651 (3)	138
N3—H3···O2	0.86	1.97	2.640 (3)	134
C2—H2A···S1	0.93	2.79	3.223 (3)	110
N4—H4···S2ⁱ	0.86	2.71	3.533 (3)	161
C15—H15B···Cg1ⁱⁱ	0.96	2.76	3.509 (4)	136

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₄O₂S₂
M_r	462.58
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.1565 (18), 11.394 (3), 14.332 (4)
α, β, γ (°)	96.414 (5), 99.066 (6), 94.085 (6)
V (Å³)	1142.1 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.50 × 0.12 × 0.06

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.880, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	13125, 4472, 2810
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.143, 1.02
No. of reflections	4472
No. of parameters	294
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.19

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.86	2.83	3.476 (3)	134
N1—H1···O1	0.86	1.95	2.651 (3)	138
N3—H3···O2	0.86	1.97	2.640 (3)	134
C2—H2A···S1	0.93	2.79	3.223 (3)	110
N4—H4···S2ⁱ	0.86	2.71	3.533 (3)	161
C15—H15B···Cg1ⁱⁱ	0.96	2.76	3.509 (4)	136

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

Acknowledgements

The authors thank 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 Universiti Malaysia Terengganu is very much appreciated.

References

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
Yamin, B. M. & Osman, U. M. (2011). Acta Cryst. E67, o1286. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2583

https://doi.org/10.1107/S1600536811035586

Open

access