N-[(3-Ethyl-phen-yl)carbamo-thio-yl]-2,2-di-phenyl-acetamide.

In the title mol-ecule, C23H22N2OS, the di-phenyl-acetyl and ethyl-benzene groups adopt a trans-cis conformation, respectively, with respect to the S atom across the (S=)C-N bonds. This conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond and a weak C-H⋯S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N-H⋯O hydrogen bonds link mol-ecules into chains along [100]. A weak C-H⋯π inter-action is also observed.

Related literature

For the biological activity of carbonyl­thio­urea derivatives, see: Zhong et al. (2008 ▶); Saeed et al. (2010 ▶). For related structures, 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 ▶). For standard bond lenths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H22N2OS

M = 374.49

Orthorhombic,

a = 10.0608 (2) Å

b = 17.9092 (5) Å

c = 10.8495 (3) Å

V = 1954.87 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.26 × 0.23 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.983

11560 measured reflections

4121 independent reflections

2885 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.098

S = 0.99

4121 reflections

253 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 1761 Friedel pairs

Flack parameter: 0.17 (9)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014268/lh5616sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014268/lh5616Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014268/lh5616Isup3.cml

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

C23H22N2OS	F(000) = 792
Mr = 374.49	Dx = 1.272 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2145 reflections
a = 10.0608 (2) Å	θ = 3.0–32.6°
b = 17.9092 (5) Å	µ = 0.18 mm−1
c = 10.8495 (3) Å	T = 100 K
V = 1954.87 (9) Å3	Plate, colourless
Z = 4	0.26 × 0.23 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	4121 independent reflections
Radiation source: fine-focus sealed tube	2885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
Tmin = 0.955, Tmax = 0.983	k = −23→19
11560 measured reflections	l = −13→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0368P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
4121 reflections	Δρmax = 0.44 e Å−3
253 parameters	Δρmin = −0.32 e Å−3
1 restraint	Absolute structure: Flack (1983), 1761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.17 (9)

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	0.31660 (6)	0.86772 (5)	0.55685 (8)	0.0304 (2)
O1	0.67282 (17)	0.76358 (11)	0.36156 (18)	0.0183 (5)
N1	0.4543 (2)	0.79237 (14)	0.3925 (2)	0.0167 (6)
N2	0.5813 (2)	0.84342 (13)	0.5464 (2)	0.0171 (6)
C1	0.4471 (3)	0.60946 (17)	0.3775 (3)	0.0228 (8)
H1A	0.5140	0.6275	0.4317	0.027*
C2	0.3680 (3)	0.54945 (18)	0.4134 (3)	0.0273 (8)
H2A	0.3806	0.5270	0.4919	0.033*
C3	0.2716 (3)	0.52269 (19)	0.3353 (3)	0.0288 (9)
H3A	0.2173	0.4819	0.3599	0.035*
C4	0.2539 (3)	0.55506 (19)	0.2211 (3)	0.0267 (8)
H4A	0.1879	0.5362	0.1667	0.032*
C5	0.3322 (3)	0.61505 (17)	0.1855 (3)	0.0218 (7)
H5A	0.3193	0.6373	0.1069	0.026*
C6	0.4296 (3)	0.64289 (17)	0.2643 (3)	0.0159 (7)
C7	0.5123 (3)	0.70924 (15)	0.2215 (3)	0.0151 (6)
H7A	0.4535	0.7410	0.1689	0.018*
C8	0.6323 (3)	0.68784 (16)	0.1434 (3)	0.0153 (7)
C9	0.6652 (3)	0.73113 (17)	0.0418 (3)	0.0228 (7)
H9A	0.6124	0.7734	0.0217	0.027*
C10	0.7742 (3)	0.7136 (2)	−0.0309 (3)	0.0269 (8)
H10A	0.7961	0.7440	−0.0997	0.032*
C11	0.8512 (3)	0.65166 (19)	−0.0030 (3)	0.0260 (8)
H11A	0.9252	0.6390	−0.0532	0.031*
C12	0.8195 (3)	0.60861 (19)	0.0980 (3)	0.0289 (8)
H12A	0.8725	0.5664	0.1180	0.035*
C13	0.7102 (3)	0.62655 (18)	0.1710 (3)	0.0229 (7)
H13A	0.6891	0.5964	0.2404	0.028*
C14	0.5563 (3)	0.75715 (16)	0.3310 (3)	0.0133 (6)
C15	0.4590 (3)	0.83515 (16)	0.5009 (3)	0.0161 (7)
C16	0.6292 (3)	0.87797 (16)	0.6550 (3)	0.0174 (7)
C17	0.7605 (3)	0.86083 (17)	0.6841 (3)	0.0228 (8)
H17A	0.8072	0.8263	0.6336	0.027*
C18	0.8250 (3)	0.89224 (18)	0.7834 (3)	0.0262 (8)
C19	0.7545 (3)	0.94264 (19)	0.8556 (3)	0.0290 (8)
H19A	0.7969	0.9658	0.9238	0.035*
C20	0.6235 (3)	0.95954 (19)	0.8292 (3)	0.0279 (8)
H20A	0.5763	0.9934	0.8805	0.034*
C21	0.5598 (3)	0.92747 (17)	0.7284 (3)	0.0215 (7)
H21A	0.4699	0.9395	0.7103	0.026*
C22	0.9695 (3)	0.8747 (2)	0.8103 (4)	0.0425 (11)
H22A	0.9778	0.8621	0.8989	0.051*
H22B	1.0225	0.9204	0.7956	0.051*
C23	1.0305 (3)	0.8111 (2)	0.7353 (3)	0.0440 (11)
H23A	1.1230	0.8036	0.7608	0.066*
H23B	1.0277	0.8239	0.6475	0.066*
H23C	0.9799	0.7652	0.7495	0.066*
H1N1	0.379 (3)	0.7853 (15)	0.366 (3)	0.019 (9)*
H1N2	0.640 (3)	0.8181 (17)	0.500 (3)	0.025 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0143 (3)	0.0422 (5)	0.0348 (5)	0.0050 (4)	0.0033 (4)	−0.0157 (5)
O1	0.0112 (9)	0.0225 (12)	0.0212 (11)	0.0009 (9)	−0.0011 (10)	−0.0068 (10)
N1	0.0095 (12)	0.0191 (15)	0.0214 (15)	−0.0001 (11)	−0.0041 (12)	−0.0051 (12)
N2	0.0100 (11)	0.0222 (14)	0.0191 (13)	0.0018 (10)	0.0008 (13)	−0.0076 (14)
C1	0.0232 (17)	0.0190 (19)	0.0263 (19)	−0.0023 (14)	−0.0034 (15)	0.0008 (16)
C2	0.035 (2)	0.025 (2)	0.0213 (17)	0.0008 (16)	0.0088 (16)	0.0028 (17)
C3	0.0222 (16)	0.026 (2)	0.039 (2)	−0.0070 (14)	0.0067 (18)	0.0000 (18)
C4	0.0216 (16)	0.027 (2)	0.0316 (19)	−0.0109 (15)	−0.0075 (16)	−0.0021 (18)
C5	0.0221 (16)	0.025 (2)	0.0177 (16)	−0.0007 (14)	−0.0055 (14)	0.0040 (15)
C6	0.0173 (15)	0.0175 (18)	0.0130 (15)	0.0045 (13)	0.0037 (13)	−0.0005 (14)
C7	0.0157 (14)	0.0151 (16)	0.0144 (15)	0.0010 (12)	−0.0018 (13)	0.0006 (14)
C8	0.0161 (14)	0.0185 (17)	0.0114 (15)	−0.0049 (13)	−0.0016 (13)	−0.0035 (14)
C9	0.0164 (15)	0.0286 (18)	0.0233 (17)	−0.0023 (13)	−0.0078 (15)	0.0042 (17)
C10	0.0249 (17)	0.037 (2)	0.0183 (18)	−0.0127 (15)	0.0014 (15)	0.0005 (17)
C11	0.0171 (15)	0.035 (2)	0.0259 (19)	−0.0096 (15)	0.0067 (15)	−0.0141 (18)
C12	0.0235 (17)	0.0252 (19)	0.038 (2)	0.0031 (15)	0.0038 (17)	−0.0054 (17)
C13	0.0240 (16)	0.0197 (18)	0.0251 (18)	0.0020 (13)	0.0051 (14)	0.0009 (16)
C14	0.0157 (13)	0.0101 (16)	0.0140 (14)	−0.0014 (12)	0.0021 (13)	0.0044 (13)
C15	0.0142 (14)	0.0149 (17)	0.0192 (16)	−0.0001 (12)	0.0033 (13)	0.0034 (15)
C16	0.0176 (14)	0.0153 (17)	0.0192 (17)	−0.0038 (13)	0.0002 (14)	−0.0003 (15)
C17	0.0189 (15)	0.0226 (19)	0.0269 (18)	−0.0020 (14)	0.0027 (15)	−0.0025 (16)
C18	0.0278 (16)	0.0238 (19)	0.0269 (18)	−0.0064 (15)	−0.0091 (16)	0.0055 (17)
C19	0.044 (2)	0.025 (2)	0.0185 (16)	−0.0138 (17)	−0.0059 (17)	0.0016 (17)
C20	0.0384 (18)	0.025 (2)	0.0202 (17)	0.0013 (16)	0.0034 (17)	−0.0042 (16)
C21	0.0225 (15)	0.0230 (19)	0.0190 (16)	0.0021 (14)	0.0013 (15)	−0.0007 (16)
C22	0.036 (2)	0.038 (2)	0.053 (3)	−0.0038 (18)	−0.024 (2)	−0.004 (2)
C23	0.0202 (18)	0.086 (3)	0.025 (2)	0.004 (2)	−0.0051 (16)	0.003 (2)

S1—C15	1.662 (3)	C9—H9A	0.9500
O1—C14	1.224 (3)	C10—C11	1.386 (5)
N1—C14	1.377 (3)	C10—H10A	0.9500
N1—C15	1.404 (4)	C11—C12	1.378 (4)
N1—H1N1	0.82 (3)	C11—H11A	0.9500
N2—C15	1.334 (3)	C12—C13	1.393 (4)
N2—C16	1.416 (4)	C12—H12A	0.9500
N2—H1N2	0.90 (3)	C13—H13A	0.9500
C1—C6	1.378 (4)	C16—C21	1.381 (4)
C1—C2	1.393 (4)	C16—C17	1.391 (4)
C1—H1A	0.9500	C17—C18	1.379 (4)
C2—C3	1.374 (4)	C17—H17A	0.9500
C2—H2A	0.9500	C18—C19	1.389 (5)
C3—C4	1.380 (5)	C18—C22	1.516 (4)
C3—H3A	0.9500	C19—C20	1.383 (4)
C4—C5	1.387 (4)	C19—H19A	0.9500
C4—H4A	0.9500	C20—C21	1.392 (4)
C5—C6	1.392 (4)	C20—H20A	0.9500
C5—H5A	0.9500	C21—H21A	0.9500
C6—C7	1.523 (4)	C22—C23	1.528 (5)
C7—C8	1.524 (4)	C22—H22A	0.9900
C7—C14	1.531 (4)	C22—H22B	0.9900
C7—H7A	1.0000	C23—H23A	0.9800
C8—C13	1.382 (4)	C23—H23B	0.9800
C8—C9	1.388 (4)	C23—H23C	0.9800
C9—C10	1.387 (4)
C14—N1—C15	129.1 (2)	C11—C12—C13	120.4 (3)
C14—N1—H1N1	117 (2)	C11—C12—H12A	119.8
C15—N1—H1N1	114 (2)	C13—C12—H12A	119.8
C15—N2—C16	132.1 (3)	C8—C13—C12	120.5 (3)
C15—N2—H1N2	109.9 (18)	C8—C13—H13A	119.7
C16—N2—H1N2	117.7 (18)	C12—C13—H13A	119.7
C6—C1—C2	120.7 (3)	O1—C14—N1	122.6 (3)
C6—C1—H1A	119.6	O1—C14—C7	122.7 (2)
C2—C1—H1A	119.6	N1—C14—C7	114.7 (2)
C3—C2—C1	120.0 (3)	N2—C15—N1	113.7 (2)
C3—C2—H2A	120.0	N2—C15—S1	128.4 (2)
C1—C2—H2A	120.0	N1—C15—S1	117.9 (2)
C2—C3—C4	119.9 (3)	C21—C16—C17	119.4 (3)
C2—C3—H3A	120.0	C21—C16—N2	126.0 (3)
C4—C3—H3A	120.0	C17—C16—N2	114.5 (3)
C3—C4—C5	120.1 (3)	C18—C17—C16	122.3 (3)
C3—C4—H4A	119.9	C18—C17—H17A	118.9
C5—C4—H4A	119.9	C16—C17—H17A	118.9
C4—C5—C6	120.4 (3)	C17—C18—C19	117.7 (3)
C4—C5—H5A	119.8	C17—C18—C22	121.2 (3)
C6—C5—H5A	119.8	C19—C18—C22	121.0 (3)
C1—C6—C5	118.8 (3)	C20—C19—C18	120.8 (3)
C1—C6—C7	122.7 (3)	C20—C19—H19A	119.6
C5—C6—C7	118.5 (3)	C18—C19—H19A	119.6
C6—C7—C8	114.0 (2)	C19—C20—C21	120.7 (3)
C6—C7—C14	111.0 (2)	C19—C20—H20A	119.6
C8—C7—C14	110.1 (2)	C21—C20—H20A	119.6
C6—C7—H7A	107.1	C16—C21—C20	119.0 (3)
C8—C7—H7A	107.1	C16—C21—H21A	120.5
C14—C7—H7A	107.1	C20—C21—H21A	120.5
C13—C8—C9	118.7 (3)	C18—C22—C23	115.9 (3)
C13—C8—C7	121.9 (3)	C18—C22—H22A	108.3
C9—C8—C7	119.4 (3)	C23—C22—H22A	108.3
C10—C9—C8	120.9 (3)	C18—C22—H22B	108.3
C10—C9—H9A	119.5	C23—C22—H22B	108.3
C8—C9—H9A	119.5	H22A—C22—H22B	107.4
C11—C10—C9	120.0 (3)	C22—C23—H23A	109.5
C11—C10—H10A	120.0	C22—C23—H23B	109.5
C9—C10—H10A	120.0	H23A—C23—H23B	109.5
C12—C11—C10	119.5 (3)	C22—C23—H23C	109.5
C12—C11—H11A	120.3	H23A—C23—H23C	109.5
C10—C11—H11A	120.3	H23B—C23—H23C	109.5
C6—C1—C2—C3	0.4 (5)	C15—N1—C14—O1	−5.2 (5)
C1—C2—C3—C4	0.3 (5)	C15—N1—C14—C7	174.6 (3)
C2—C3—C4—C5	−0.7 (5)	C6—C7—C14—O1	114.1 (3)
C3—C4—C5—C6	0.3 (5)	C8—C7—C14—O1	−13.1 (4)
C2—C1—C6—C5	−0.8 (4)	C6—C7—C14—N1	−65.8 (3)
C2—C1—C6—C7	179.2 (3)	C8—C7—C14—N1	167.0 (2)
C4—C5—C6—C1	0.4 (4)	C16—N2—C15—N1	−176.0 (3)
C4—C5—C6—C7	−179.5 (3)	C16—N2—C15—S1	3.2 (5)
C1—C6—C7—C8	94.9 (3)	C14—N1—C15—N2	2.0 (4)
C5—C6—C7—C8	−85.2 (3)	C14—N1—C15—S1	−177.3 (2)
C1—C6—C7—C14	−30.1 (4)	C15—N2—C16—C21	−16.1 (5)
C5—C6—C7—C14	149.8 (3)	C15—N2—C16—C17	166.4 (3)
C6—C7—C8—C13	−40.4 (4)	C21—C16—C17—C18	−0.7 (4)
C14—C7—C8—C13	85.1 (3)	N2—C16—C17—C18	177.0 (3)
C6—C7—C8—C9	139.9 (3)	C16—C17—C18—C19	−0.1 (5)
C14—C7—C8—C9	−94.6 (3)	C16—C17—C18—C22	−177.8 (3)
C13—C8—C9—C10	−0.1 (4)	C17—C18—C19—C20	1.0 (5)
C7—C8—C9—C10	179.6 (3)	C22—C18—C19—C20	178.7 (3)
C8—C9—C10—C11	0.6 (4)	C18—C19—C20—C21	−1.2 (5)
C9—C10—C11—C12	−0.9 (4)	C17—C16—C21—C20	0.5 (4)
C10—C11—C12—C13	0.7 (4)	N2—C16—C21—C20	−176.8 (3)
C9—C8—C13—C12	−0.1 (4)	C19—C20—C21—C16	0.4 (4)
C7—C8—C13—C12	−179.8 (3)	C17—C18—C22—C23	−10.1 (5)
C11—C12—C13—C8	−0.2 (4)	C19—C18—C22—C23	172.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.90 (3)	1.82 (3)	2.630 (3)	148 (3)
C21—H21A···S1	0.95	2.61	3.255 (3)	126
N1—H1N1···O1i	0.82 (3)	2.25 (3)	3.023 (3)	157 (3)
C7—H7A···Cgii	1.00	2.87	3.844 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.90 (3)	1.82 (3)	2.630 (3)	148 (3)
C21—H21A⋯S1	0.95	2.61	3.255 (3)	126
N1—H1N1⋯O1i	0.82 (3)	2.25 (3)	3.023 (3)	157 (3)
C7—H7A⋯Cg ii	1.00	2.87	3.844 (3)	166

Symmetry codes: (i) ; (ii) .