N-[(2,6-Di­ethyl­phen­yl)carbamo­thio­yl]-2,2-di­phenyl­acetamide

Yusof, M.S.M.; Razali, N.R.; Arshad, S.; Rahman, A.A.; Razak, I.A.

doi:10.1107/S1600536813013354

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o967

doi:10.1107/S1600536813013354

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N-[(2,6-Diethylphenyl)carbamothioyl]-2,2-diphenylacetamide

Mohd Sukeri Mohd Yusof,^a Nur Rafikah Razali,^a Suhana Arshad,^b ‡ Azhar Abdul Rahman ^b and Ibrahim Abdul Razak ^b ^*§

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 7 May 2013; accepted 15 May 2013; online 25 May 2013)

In the title compound, C₂₅H₂₆N₂OS, the diethyl-substituted benzene ring forms dihedral angles of 67.38 (9) and 55.32 (9)° with the terminal benzene rings. The molecule adopts a trans–cis conformation with respect to the orientations of the diphenylmethane and 1,3-diethylbenzene groups with respect to the S atom across the C—N bonds. This conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, pairs of N—H⋯S hydrogen bonds link the molecules into inversion dimers, forming R₂²(6) loops. The dimer linkage is reinforced by a pair of C—H⋯S hydrogen bonds, which generate R₂²(8) loops. Weak C—H⋯π and π–π [centroid–centroid seperation = 3.8821 (10) Å] interactions also occur in the crystal structure.

Related literature

For related structures and backgroud to thiourea derivatives, see: Yusof et al. (2012a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₅H₂₆N₂OS
M_r = 402.54
Triclinic, $[P \overline 1]$
a = 8.0091 (1) Å
b = 11.7289 (2) Å
c = 11.8923 (2) Å
α = 79.008 (1)°
β = 80.628 (1)°
γ = 83.936 (1)°
V = 1078.79 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.41 × 0.17 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.934, T_max = 0.987
20294 measured reflections
3767 independent reflections
3123 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.06
3767 reflections
272 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.86 (2)	1.96 (2)	2.6702 (19)	140 (2)
N1—H1N1⋯S1ⁱ	0.85 (2)	2.59 (2)	3.4225 (16)	167.4 (18)
C7—H7A⋯S1ⁱ	1.00	2.64	3.6172 (17)	165
C10—H10A⋯Cg1ⁱⁱ	0.95	2.56	3.3859 (19)	146
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013354/hb7080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013354/hb7080Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013354/hb7080Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of thiourea derivatives (Yusof et al., 2012a,b), we now describe the structure of the title compound, (I), (Fig. 1).

The bond lengths and angles are comparable to those in related structure (Yusof et al., 2012a,b). The diethyl-substituted benzene ring (C16–C21) forms dihedral angles of 67.38 (9) and 55.32 (9)° with the terminal benzene rings (C1–C6 & C8–C13), respectively. The molecule adopts a trans-cis conformation with respect to the position of diphenylmethane and 1,3-diethylbenzene groups to the sulfur (S1) atom across the C–N bonds, respectively. These configuration further resulting in an S(6) graph-set motif (Bernstein et al., 1995) via intra-molecular N2—H1N2···O1 hydrogen bond (Table 1).

In the crystal (Fig. 2), molecules are linked into dimers via N1—H1N1···S1 and C7—H7A···S1 hydrogen bonds (Table 1), generating R²₂(6) and R²₂(8) loops. C10—H10A···Cg1 (Table 1) interactions and π–π interactions of Cg1···Cg1 = 3.8821 (10) Å (symmetry code: -x, 2-y, 2-z) further stabilized the crystal structure (Cg1 is the centroid of C1–C6).

Related literature top

For related structures and backgroud to thiourea derivatives, see: Yusof et al. (2012a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

An acetone (30 ml) solution of 2,6-diethylaniline (2.01 g, 13.5 mmol) was added to a round-bottom flask containing 2,2-diphenylacetyl chloride (3.10 g, 13.5 mmol) and ammonium thiocyanate (1.03 g, 13.5 mmol). The mixture was put at reflux for 2.5 h then filtered off and left to evaporate at room temperature. The colourless precipitate obtained was washed with water and cold ethanol. Colourless plates were obtained by recrystallization of the precipitate from MeOH solution.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

N-[(2,6-Diethylphenyl)carbamothioyl]-2,2-diphenylacetamide top

Crystal data top

C₂₅H₂₆N₂OS	Z = 2
M_r = 402.54	F(000) = 428
Triclinic, P1	D_x = 1.239 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0091 (1) Å	Cell parameters from 7540 reflections
b = 11.7289 (2) Å	θ = 2.7–31.3°
c = 11.8923 (2) Å	µ = 0.17 mm⁻¹
α = 79.008 (1)°	T = 100 K
β = 80.628 (1)°	Plate, colourless
γ = 83.936 (1)°	0.41 × 0.17 × 0.08 mm
V = 1078.79 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3767 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.934, T_max = 0.987	k = −13→13
20294 measured reflections	l = −13→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0256P)² + 0.7158P] where P = (F_o² + 2F_c²)/3
3767 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₅H₂₆N₂OS	γ = 83.936 (1)°
M_r = 402.54	V = 1078.79 (3) Å³
Triclinic, P1	Z = 2
a = 8.0091 (1) Å	Mo Kα radiation
b = 11.7289 (2) Å	µ = 0.17 mm⁻¹
c = 11.8923 (2) Å	T = 100 K
α = 79.008 (1)°	0.41 × 0.17 × 0.08 mm
β = 80.628 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3767 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3123 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.987	R_int = 0.037
20294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
3767 reflections	Δρ_min = −0.25 e Å⁻³
272 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.14725 (6)	0.37823 (4)	0.90032 (4)	0.02277 (14)
O1	0.23366 (16)	0.74355 (10)	0.69663 (10)	0.0209 (3)
N1	0.1116 (2)	0.60788 (12)	0.84279 (13)	0.0175 (3)
H1N1	0.041 (3)	0.6010 (17)	0.9051 (18)	0.027 (6)*
N2	0.32515 (19)	0.51541 (13)	0.72816 (13)	0.0176 (3)
H1N2	0.334 (3)	0.5850 (19)	0.6903 (18)	0.030 (6)*
C1	0.1681 (2)	0.88822 (15)	0.95814 (15)	0.0192 (4)
H1A	0.1494	0.8182	1.0122	0.023*
C2	0.2650 (2)	0.96979 (16)	0.98238 (16)	0.0214 (4)
H2A	0.3124	0.9555	1.0525	0.026*
C3	0.2921 (2)	1.07207 (16)	0.90366 (16)	0.0226 (4)
H3A	0.3599	1.1275	0.9190	0.027*
C4	0.2204 (2)	1.09329 (15)	0.80297 (16)	0.0217 (4)
H4A	0.2377	1.1640	0.7498	0.026*
C5	0.1228 (2)	1.01165 (15)	0.77866 (16)	0.0191 (4)
H5A	0.0733	1.0272	0.7094	0.023*
C6	0.0981 (2)	0.90785 (14)	0.85548 (15)	0.0151 (4)
C7	0.0022 (2)	0.81080 (14)	0.83243 (14)	0.0154 (4)
H7A	−0.0538	0.7715	0.9094	0.018*
C8	−0.1370 (2)	0.84747 (14)	0.75624 (15)	0.0165 (4)
C9	−0.3053 (2)	0.84527 (15)	0.80968 (16)	0.0194 (4)
H9A	−0.3293	0.8223	0.8913	0.023*
C10	−0.4384 (2)	0.87616 (15)	0.74551 (16)	0.0218 (4)
H10A	−0.5525	0.8745	0.7832	0.026*
C11	−0.4046 (3)	0.90924 (16)	0.62722 (17)	0.0239 (4)
H11A	−0.4954	0.9304	0.5831	0.029*
C12	−0.2384 (3)	0.91175 (17)	0.57251 (16)	0.0261 (5)
H12A	−0.2155	0.9349	0.4908	0.031*
C13	−0.1047 (2)	0.88063 (16)	0.63647 (16)	0.0219 (4)
H13A	0.0091	0.8820	0.5982	0.026*
C14	0.1283 (2)	0.71976 (15)	0.78288 (15)	0.0159 (4)
C15	0.2009 (2)	0.50521 (15)	0.81792 (15)	0.0170 (4)
C16	0.4354 (2)	0.41906 (14)	0.69377 (15)	0.0164 (4)
C17	0.4107 (2)	0.37685 (15)	0.59603 (15)	0.0196 (4)
C18	0.5229 (3)	0.28617 (16)	0.56247 (17)	0.0271 (5)
H18A	0.5095	0.2562	0.4959	0.032*
C19	0.6536 (3)	0.23894 (17)	0.62419 (19)	0.0310 (5)
H19A	0.7280	0.1764	0.6006	0.037*
C20	0.6758 (2)	0.28280 (16)	0.72028 (18)	0.0258 (5)
H20A	0.7659	0.2500	0.7622	0.031*
C21	0.5685 (2)	0.37423 (15)	0.75657 (15)	0.0195 (4)
C22	0.6019 (3)	0.42551 (17)	0.85727 (16)	0.0260 (5)
H22A	0.6723	0.3677	0.9053	0.031*
H22B	0.4926	0.4417	0.9060	0.031*
C23	0.6922 (3)	0.53785 (18)	0.81866 (18)	0.0333 (5)
H23A	0.7139	0.5662	0.8869	0.050*
H23B	0.6204	0.5969	0.7745	0.050*
H23C	0.8001	0.5226	0.7698	0.050*
C24	0.2659 (3)	0.42388 (17)	0.52918 (17)	0.0278 (5)
H24A	0.3007	0.4157	0.4471	0.033*
H24B	0.2414	0.5079	0.5318	0.033*
C25	0.1047 (3)	0.36140 (18)	0.57675 (19)	0.0326 (5)
H25A	0.0156	0.3941	0.5296	0.049*
H25B	0.0670	0.3719	0.6570	0.049*
H25C	0.1280	0.2781	0.5741	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0282 (3)	0.0146 (2)	0.0217 (3)	−0.0026 (2)	0.0066 (2)	−0.00198 (18)
O1	0.0191 (7)	0.0186 (6)	0.0223 (7)	−0.0033 (5)	0.0043 (6)	−0.0022 (5)
N1	0.0161 (8)	0.0163 (8)	0.0178 (8)	−0.0019 (6)	0.0040 (7)	−0.0024 (6)
N2	0.0186 (9)	0.0137 (8)	0.0181 (8)	−0.0010 (6)	0.0015 (7)	−0.0009 (6)
C1	0.0192 (10)	0.0180 (9)	0.0191 (10)	0.0007 (8)	−0.0016 (8)	−0.0023 (7)
C2	0.0208 (11)	0.0249 (10)	0.0210 (10)	−0.0003 (8)	−0.0064 (8)	−0.0079 (8)
C3	0.0195 (11)	0.0236 (10)	0.0270 (11)	−0.0042 (8)	−0.0011 (8)	−0.0106 (8)
C4	0.0233 (11)	0.0166 (9)	0.0241 (10)	−0.0039 (8)	0.0012 (8)	−0.0032 (8)
C5	0.0187 (10)	0.0194 (9)	0.0188 (9)	−0.0005 (8)	−0.0013 (8)	−0.0039 (7)
C6	0.0110 (9)	0.0165 (9)	0.0178 (9)	0.0006 (7)	0.0004 (7)	−0.0057 (7)
C7	0.0133 (9)	0.0166 (9)	0.0152 (9)	−0.0021 (7)	0.0001 (7)	−0.0012 (7)
C8	0.0162 (10)	0.0125 (8)	0.0218 (10)	−0.0026 (7)	−0.0015 (8)	−0.0058 (7)
C9	0.0203 (10)	0.0183 (9)	0.0198 (10)	−0.0032 (8)	0.0009 (8)	−0.0059 (7)
C10	0.0140 (10)	0.0232 (10)	0.0297 (11)	−0.0012 (8)	−0.0026 (8)	−0.0092 (8)
C11	0.0220 (11)	0.0230 (10)	0.0304 (11)	−0.0007 (8)	−0.0115 (9)	−0.0083 (8)
C12	0.0307 (12)	0.0293 (11)	0.0188 (10)	−0.0037 (9)	−0.0059 (9)	−0.0026 (8)
C13	0.0186 (11)	0.0255 (10)	0.0214 (10)	−0.0052 (8)	−0.0003 (8)	−0.0038 (8)
C14	0.0143 (10)	0.0173 (9)	0.0180 (9)	−0.0050 (7)	−0.0052 (8)	−0.0035 (7)
C15	0.0155 (10)	0.0180 (9)	0.0182 (9)	−0.0018 (7)	−0.0031 (8)	−0.0043 (7)
C16	0.0144 (10)	0.0157 (9)	0.0180 (9)	−0.0033 (7)	0.0016 (7)	−0.0026 (7)
C17	0.0173 (10)	0.0222 (10)	0.0191 (10)	−0.0107 (8)	0.0030 (8)	−0.0027 (8)
C18	0.0269 (12)	0.0276 (11)	0.0285 (11)	−0.0135 (9)	0.0090 (9)	−0.0142 (9)
C19	0.0224 (12)	0.0218 (10)	0.0470 (13)	−0.0013 (9)	0.0087 (10)	−0.0136 (9)
C20	0.0164 (10)	0.0225 (10)	0.0372 (12)	−0.0012 (8)	−0.0027 (9)	−0.0030 (9)
C21	0.0185 (10)	0.0176 (9)	0.0218 (10)	−0.0050 (8)	−0.0010 (8)	−0.0018 (8)
C22	0.0252 (11)	0.0288 (11)	0.0241 (10)	0.0000 (9)	−0.0078 (9)	−0.0027 (8)
C23	0.0348 (13)	0.0402 (12)	0.0304 (12)	−0.0117 (10)	−0.0077 (10)	−0.0125 (10)
C24	0.0294 (12)	0.0324 (11)	0.0229 (10)	−0.0111 (9)	−0.0050 (9)	−0.0022 (9)
C25	0.0254 (12)	0.0320 (11)	0.0409 (13)	−0.0077 (9)	−0.0107 (10)	0.0003 (10)

Geometric parameters (Å, º) top

S1—C15	1.6748 (17)	C11—C12	1.384 (3)
O1—C14	1.225 (2)	C11—H11A	0.9500
N1—C14	1.377 (2)	C12—C13	1.391 (3)
N1—C15	1.391 (2)	C12—H12A	0.9500
N1—H1N1	0.85 (2)	C13—H13A	0.9500
N2—C15	1.332 (2)	C16—C17	1.396 (3)
N2—C16	1.439 (2)	C16—C21	1.401 (3)
N2—H1N2	0.86 (2)	C17—C18	1.393 (3)
C1—C2	1.391 (3)	C17—C24	1.510 (3)
C1—C6	1.395 (2)	C18—C19	1.383 (3)
C1—H1A	0.9500	C18—H18A	0.9500
C2—C3	1.387 (3)	C19—C20	1.383 (3)
C2—H2A	0.9500	C19—H19A	0.9500
C3—C4	1.380 (3)	C20—C21	1.391 (3)
C3—H3A	0.9500	C20—H20A	0.9500
C4—C5	1.396 (3)	C21—C22	1.510 (3)
C4—H4A	0.9500	C22—C23	1.527 (3)
C5—C6	1.387 (2)	C22—H22A	0.9900
C5—H5A	0.9500	C22—H22B	0.9900
C6—C7	1.527 (2)	C23—H23A	0.9800
C7—C14	1.525 (2)	C23—H23B	0.9800
C7—C8	1.525 (2)	C23—H23C	0.9800
C7—H7A	1.0000	C24—C25	1.526 (3)
C8—C13	1.392 (2)	C24—H24A	0.9900
C8—C9	1.394 (2)	C24—H24B	0.9900
C9—C10	1.389 (3)	C25—H25A	0.9800
C9—H9A	0.9500	C25—H25B	0.9800
C10—C11	1.376 (3)	C25—H25C	0.9800
C10—H10A	0.9500

C14—N1—C15	128.46 (15)	O1—C14—N1	122.87 (16)
C14—N1—H1N1	115.8 (14)	O1—C14—C7	123.13 (15)
C15—N1—H1N1	115.7 (14)	N1—C14—C7	113.98 (14)
C15—N2—C16	124.03 (15)	N2—C15—N1	116.69 (15)
C15—N2—H1N2	114.5 (14)	N2—C15—S1	124.24 (14)
C16—N2—H1N2	121.5 (14)	N1—C15—S1	119.07 (13)
C2—C1—C6	120.85 (16)	C17—C16—C21	122.22 (17)
C2—C1—H1A	119.6	C17—C16—N2	118.95 (16)
C6—C1—H1A	119.6	C21—C16—N2	118.77 (16)
C3—C2—C1	119.62 (17)	C18—C17—C16	117.69 (18)
C3—C2—H2A	120.2	C18—C17—C24	119.97 (17)
C1—C2—H2A	120.2	C16—C17—C24	122.32 (17)
C4—C3—C2	119.93 (17)	C19—C18—C17	121.23 (18)
C4—C3—H3A	120.0	C19—C18—H18A	119.4
C2—C3—H3A	120.0	C17—C18—H18A	119.4
C3—C4—C5	120.51 (17)	C20—C19—C18	119.91 (18)
C3—C4—H4A	119.7	C20—C19—H19A	120.0
C5—C4—H4A	119.7	C18—C19—H19A	120.0
C6—C5—C4	120.08 (17)	C19—C20—C21	121.10 (19)
C6—C5—H5A	120.0	C19—C20—H20A	119.4
C4—C5—H5A	120.0	C21—C20—H20A	119.4
C5—C6—C1	118.98 (16)	C20—C21—C16	117.83 (17)
C5—C6—C7	123.53 (16)	C20—C21—C22	120.08 (18)
C1—C6—C7	117.46 (15)	C16—C21—C22	122.03 (16)
C14—C7—C8	109.72 (14)	C21—C22—C23	112.66 (16)
C14—C7—C6	109.54 (14)	C21—C22—H22A	109.1
C8—C7—C6	116.82 (14)	C23—C22—H22A	109.1
C14—C7—H7A	106.7	C21—C22—H22B	109.1
C8—C7—H7A	106.7	C23—C22—H22B	109.1
C6—C7—H7A	106.7	H22A—C22—H22B	107.8
C13—C8—C9	118.51 (17)	C22—C23—H23A	109.5
C13—C8—C7	123.51 (16)	C22—C23—H23B	109.5
C9—C8—C7	117.97 (15)	H23A—C23—H23B	109.5
C10—C9—C8	121.07 (17)	C22—C23—H23C	109.5
C10—C9—H9A	119.5	H23A—C23—H23C	109.5
C8—C9—H9A	119.5	H23B—C23—H23C	109.5
C11—C10—C9	119.79 (17)	C17—C24—C25	112.69 (16)
C11—C10—H10A	120.1	C17—C24—H24A	109.1
C9—C10—H10A	120.1	C25—C24—H24A	109.1
C10—C11—C12	120.03 (18)	C17—C24—H24B	109.1
C10—C11—H11A	120.0	C25—C24—H24B	109.1
C12—C11—H11A	120.0	H24A—C24—H24B	107.8
C11—C12—C13	120.37 (18)	C24—C25—H25A	109.5
C11—C12—H12A	119.8	C24—C25—H25B	109.5
C13—C12—H12A	119.8	H25A—C25—H25B	109.5
C12—C13—C8	120.23 (17)	C24—C25—H25C	109.5
C12—C13—H13A	119.9	H25A—C25—H25C	109.5
C8—C13—H13A	119.9	H25B—C25—H25C	109.5

C6—C1—C2—C3	0.1 (3)	C6—C7—C14—O1	−54.8 (2)
C1—C2—C3—C4	1.2 (3)	C8—C7—C14—N1	−104.38 (17)
C2—C3—C4—C5	−1.0 (3)	C6—C7—C14—N1	126.15 (16)
C3—C4—C5—C6	−0.4 (3)	C16—N2—C15—N1	176.91 (16)
C4—C5—C6—C1	1.7 (3)	C16—N2—C15—S1	−3.3 (3)
C4—C5—C6—C7	−176.24 (16)	C14—N1—C15—N2	3.8 (3)
C2—C1—C6—C5	−1.6 (3)	C14—N1—C15—S1	−176.01 (15)
C2—C1—C6—C7	176.50 (16)	C15—N2—C16—C17	104.9 (2)
C5—C6—C7—C14	96.32 (19)	C15—N2—C16—C21	−77.9 (2)
C1—C6—C7—C14	−81.68 (18)	C21—C16—C17—C18	0.7 (3)
C5—C6—C7—C8	−29.2 (2)	N2—C16—C17—C18	177.83 (15)
C1—C6—C7—C8	152.83 (16)	C21—C16—C17—C24	179.14 (16)
C14—C7—C8—C13	−49.6 (2)	N2—C16—C17—C24	−3.8 (2)
C6—C7—C8—C13	75.8 (2)	C16—C17—C18—C19	0.4 (3)
C14—C7—C8—C9	129.11 (16)	C24—C17—C18—C19	−177.99 (17)
C6—C7—C8—C9	−105.49 (18)	C17—C18—C19—C20	−0.8 (3)
C13—C8—C9—C10	−0.5 (3)	C18—C19—C20—C21	0.0 (3)
C7—C8—C9—C10	−179.22 (15)	C19—C20—C21—C16	1.1 (3)
C8—C9—C10—C11	0.2 (3)	C19—C20—C21—C22	−176.21 (17)
C9—C10—C11—C12	0.0 (3)	C17—C16—C21—C20	−1.5 (3)
C10—C11—C12—C13	0.2 (3)	N2—C16—C21—C20	−178.60 (15)
C11—C12—C13—C8	−0.5 (3)	C17—C16—C21—C22	175.75 (16)
C9—C8—C13—C12	0.6 (3)	N2—C16—C21—C22	−1.3 (2)
C7—C8—C13—C12	179.27 (16)	C20—C21—C22—C23	99.3 (2)
C15—N1—C14—O1	−2.0 (3)	C16—C21—C22—C23	−77.9 (2)
C15—N1—C14—C7	177.14 (16)	C18—C17—C24—C25	90.5 (2)
C8—C7—C14—O1	74.7 (2)	C16—C17—C24—C25	−87.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.86 (2)	1.96 (2)	2.6702 (19)	140 (2)
N1—H1N1···S1ⁱ	0.85 (2)	2.59 (2)	3.4225 (16)	167.4 (18)
C7—H7A···S1ⁱ	1.00	2.64	3.6172 (17)	165
C10—H10A···Cg1ⁱⁱ	0.95	2.56	3.3859 (19)	146

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂OS
M_r	402.54
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.0091 (1), 11.7289 (2), 11.8923 (2)
α, β, γ (°)	79.008 (1), 80.628 (1), 83.936 (1)
V (Å³)	1078.79 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.41 × 0.17 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.934, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	20294, 3767, 3123
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.087, 1.06
No. of reflections	3767
No. of parameters	272
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.86 (2)	1.96 (2)	2.6702 (19)	140 (2)
N1—H1N1···S1ⁱ	0.85 (2)	2.59 (2)	3.4225 (16)	167.4 (18)
C7—H7A···S1ⁱ	1.00	2.64	3.6172 (17)	165
C10—H10A···Cg1ⁱⁱ	0.95	2.56	3.3859 (19)	146

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

Footnotes

‡Thomson Reuters ResearcherID: F-9119-2012.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811151 to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science 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
Yusof, M. S. M., Arshad, S., Razak, I. A. & Rahman, A. A. (2012b). Acta Cryst. E68, o2670. CSD CrossRef IUCr Journals Google Scholar
Yusof, M. S. M., Mutalib, S. F. A., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o982. CSD CrossRef IUCr Journals Google Scholar

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