N-[(2,6-Di-ethyl-phen-yl)carbamo-thio-yl]-2,2-di-phenyl-acetamide.

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 mol-ecule adopts a trans-cis conformation with respect to the orientations of the di-phenyl-methane and 1,3-di-ethyl-benzene groups with respect to the S atom across the C-N bonds. This conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, pairs of N-H⋯S hydrogen bonds link the mol-ecules into inversion dimers, forming R 2 (2)(6) loops. The dimer linkage is reinforced by a pair of C-H⋯S hydrogen bonds, which generate R 2 (2)(8) loops. Weak C-H⋯π and π-π [centroid-centroid seperation = 3.8821 (10) Å] inter-actions 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 = 402.54

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.087

S = 1.06

3767 reflections

272 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013354/hb7080sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013354/hb7080Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H26N2OS	Z = 2
Mr = 402.54	F(000) = 428
Triclinic, P1	Dx = 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

Bruker SMART APEXII CCD diffractometer	3767 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.934, Tmax = 0.987	k = −13→13
20294 measured reflections	l = −13→14

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(Fo2) + (0.0256P)2 + 0.7158P] where P = (Fo2 + 2Fc2)/3
3767 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .