(E)-3-Anilino-2-benzoyl-3-(methyl-sulfan-yl)acrylonitrile.

In the title acrylonitrile derivative, C(17)H(14)N(2)OS, the central amino-acryl-aldehyde O=C-C=C-NH unit, wherein an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif, is approximately planar, with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms. This plane makes dihedral angles of 41.04 (9) and 84.86 (10)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 54.82 (10)°. An intra-molecular C-H⋯N hydrogen bond is also present. In the crystal, weak C-H⋯π and π-π inter-actions, with a centroid-centroid distance of 3.8526 (14) Å, are observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002 ▶); Sączewski et al. (2004 ▶); Sommen et al. (2002 ▶, 2003 ▶); Rudorf & Augustin (1977 ▶).

Experimental

Crystal data

C17H14N2OS

M = 294.37

Monoclinic,

a = 8.7522 (2) Å

b = 10.8464 (3) Å

c = 16.1156 (4) Å

β = 103.968 (2)°

V = 1484.62 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.93 mm−1

T = 296 K

0.58 × 0.52 × 0.34 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.401, T max = 0.556

9777 measured reflections

2603 independent reflections

2403 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.04

2603 reflections

197 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.23 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013475/is5105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013475/is5105Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013475/is5105Isup3.cml

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

C17H14N2OS	F(000) = 616
Mr = 294.37	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2603 reflections
a = 8.7522 (2) Å	θ = 5.0–67.5°
b = 10.8464 (3) Å	µ = 1.93 mm−1
c = 16.1156 (4) Å	T = 296 K
β = 103.968 (2)°	Block, colorless
V = 1484.62 (7) Å3	0.58 × 0.52 × 0.34 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2603 independent reflections
Radiation source: fine-focus sealed tube	2403 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 67.5°, θmin = 5.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
Tmin = 0.401, Tmax = 0.556	k = −12→12
9777 measured reflections	l = −19→19

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.3429P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2603 reflections	Δρmax = 0.23 e Å−3
197 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.26713 (5)	0.35557 (4)	0.12096 (3)	0.05369 (19)
O1	0.76575 (17)	0.35293 (12)	0.07292 (10)	0.0674 (4)
N1	0.48494 (19)	0.25937 (13)	0.05485 (10)	0.0525 (4)
N2	0.4752 (2)	0.65992 (13)	0.16908 (13)	0.0639 (4)
C1	0.84541 (18)	0.53504 (14)	0.14953 (10)	0.0427 (4)
C2	0.9477 (2)	0.57125 (16)	0.10025 (11)	0.0520 (4)
H2A	0.9370	0.5375	0.0461	0.062*
C3	1.0652 (2)	0.65671 (18)	0.13054 (15)	0.0630 (5)
H3A	1.1317	0.6813	0.0965	0.076*
C4	1.0834 (2)	0.70502 (17)	0.21094 (15)	0.0649 (5)
H4A	1.1628	0.7621	0.2316	0.078*
C5	0.9841 (2)	0.66911 (18)	0.26115 (13)	0.0605 (5)
H5A	0.9977	0.7016	0.3159	0.073*
C6	0.8640 (2)	0.58504 (16)	0.23089 (11)	0.0507 (4)
H6A	0.7964	0.5623	0.2648	0.061*
C7	0.7250 (2)	0.43946 (15)	0.11312 (10)	0.0471 (4)
C8	0.56634 (19)	0.45013 (14)	0.12432 (10)	0.0439 (4)
C9	0.4545 (2)	0.35497 (13)	0.09959 (10)	0.0438 (4)
C10	0.51581 (19)	0.56593 (14)	0.15039 (11)	0.0469 (4)
C11	0.3008 (2)	0.40943 (17)	0.22941 (11)	0.0557 (4)
H11A	0.2120	0.3887	0.2519	0.084*
H11B	0.3146	0.4973	0.2307	0.084*
H11C	0.3937	0.3711	0.2635	0.084*
C12	0.3870 (2)	0.15146 (13)	0.03407 (11)	0.0446 (4)
C13	0.4078 (3)	0.05512 (18)	0.09040 (12)	0.0640 (5)
H13A	0.4838	0.0595	0.1418	0.077*
C14	0.3149 (3)	−0.04908 (18)	0.07019 (14)	0.0696 (6)
H14A	0.3281	−0.1148	0.1083	0.084*
C15	0.2036 (3)	−0.05567 (17)	−0.00557 (13)	0.0624 (5)
H15A	0.1411	−0.1256	−0.0189	0.075*
C16	0.1846 (3)	0.04131 (19)	−0.06189 (13)	0.0680 (5)
H16A	0.1087	0.0369	−0.1133	0.082*
C17	0.2775 (3)	0.14547 (16)	−0.04263 (12)	0.0580 (5)
H17A	0.2659	0.2106	−0.0812	0.070*
H1N1	0.578 (3)	0.265 (2)	0.0390 (16)	0.083 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0462 (3)	0.0578 (3)	0.0579 (3)	−0.00653 (16)	0.01425 (19)	−0.01599 (17)
O1	0.0598 (8)	0.0556 (8)	0.0942 (10)	−0.0063 (6)	0.0328 (7)	−0.0289 (7)
N1	0.0539 (9)	0.0434 (7)	0.0649 (9)	−0.0093 (6)	0.0235 (7)	−0.0163 (6)
N2	0.0534 (9)	0.0381 (8)	0.1009 (13)	−0.0011 (6)	0.0200 (8)	−0.0108 (7)
C1	0.0400 (8)	0.0378 (7)	0.0502 (8)	0.0055 (6)	0.0105 (6)	0.0008 (6)
C2	0.0481 (9)	0.0536 (9)	0.0564 (9)	0.0045 (7)	0.0164 (7)	−0.0001 (7)
C3	0.0478 (10)	0.0568 (11)	0.0874 (14)	−0.0016 (8)	0.0224 (9)	0.0082 (9)
C4	0.0455 (9)	0.0486 (10)	0.0956 (14)	−0.0029 (7)	0.0071 (9)	−0.0058 (9)
C5	0.0538 (10)	0.0562 (10)	0.0638 (11)	0.0083 (8)	−0.0007 (8)	−0.0141 (8)
C6	0.0484 (9)	0.0517 (9)	0.0516 (9)	0.0048 (7)	0.0111 (7)	−0.0011 (7)
C7	0.0495 (9)	0.0400 (8)	0.0528 (9)	0.0006 (7)	0.0140 (7)	−0.0032 (6)
C8	0.0449 (8)	0.0358 (7)	0.0513 (8)	−0.0014 (6)	0.0123 (7)	−0.0048 (6)
C9	0.0474 (9)	0.0384 (8)	0.0448 (8)	0.0001 (6)	0.0094 (6)	−0.0016 (6)
C10	0.0422 (8)	0.0379 (8)	0.0602 (9)	−0.0042 (6)	0.0115 (7)	−0.0026 (7)
C11	0.0698 (11)	0.0484 (9)	0.0520 (9)	−0.0024 (8)	0.0207 (8)	−0.0035 (7)
C12	0.0482 (9)	0.0361 (8)	0.0520 (9)	−0.0015 (6)	0.0170 (7)	−0.0088 (6)
C13	0.0721 (12)	0.0561 (10)	0.0566 (10)	−0.0033 (9)	0.0014 (9)	0.0047 (8)
C14	0.0857 (14)	0.0452 (10)	0.0781 (13)	−0.0034 (9)	0.0200 (11)	0.0149 (9)
C15	0.0684 (12)	0.0427 (9)	0.0803 (13)	−0.0132 (8)	0.0260 (10)	−0.0120 (8)
C16	0.0713 (12)	0.0612 (11)	0.0638 (11)	−0.0144 (9)	0.0015 (9)	−0.0082 (9)
C17	0.0689 (12)	0.0443 (9)	0.0576 (10)	−0.0052 (8)	0.0089 (9)	0.0030 (7)

S1—C9	1.7549 (17)	C6—H6A	0.9300
S1—C11	1.7983 (17)	C7—C8	1.447 (2)
O1—C7	1.241 (2)	C8—C9	1.412 (2)
N1—C9	1.326 (2)	C8—C10	1.428 (2)
N1—C12	1.441 (2)	C11—H11A	0.9600
N1—H1N1	0.91 (3)	C11—H11B	0.9600
N2—C10	1.144 (2)	C11—H11C	0.9600
C1—C2	1.389 (2)	C12—C13	1.367 (3)
C1—C6	1.392 (2)	C12—C17	1.371 (3)
C1—C7	1.494 (2)	C13—C14	1.385 (3)
C2—C3	1.383 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.367 (3)
C3—C4	1.371 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.373 (3)
C4—C5	1.379 (3)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.383 (3)
C5—C6	1.388 (3)	C16—H16A	0.9300
C5—H5A	0.9300	C17—H17A	0.9300
C9—S1—C11	104.50 (9)	N1—C9—C8	120.54 (16)
C9—N1—C12	125.09 (15)	N1—C9—S1	115.44 (13)
C9—N1—H1N1	114.4 (17)	C8—C9—S1	123.98 (12)
C12—N1—H1N1	120.4 (17)	N2—C10—C8	178.1 (2)
C2—C1—C6	118.92 (15)	S1—C11—H11A	109.5
C2—C1—C7	117.55 (14)	S1—C11—H11B	109.5
C6—C1—C7	123.47 (15)	H11A—C11—H11B	109.5
C3—C2—C1	120.98 (17)	S1—C11—H11C	109.5
C3—C2—H2A	119.5	H11A—C11—H11C	109.5
C1—C2—H2A	119.5	H11B—C11—H11C	109.5
C4—C3—C2	119.76 (19)	C13—C12—C17	120.98 (16)
C4—C3—H3A	120.1	C13—C12—N1	119.33 (16)
C2—C3—H3A	120.1	C17—C12—N1	119.67 (15)
C3—C4—C5	120.06 (17)	C12—C13—C14	119.40 (18)
C3—C4—H4A	120.0	C12—C13—H13A	120.3
C5—C4—H4A	120.0	C14—C13—H13A	120.3
C4—C5—C6	120.69 (18)	C15—C14—C13	120.27 (18)
C4—C5—H5A	119.7	C15—C14—H14A	119.9
C6—C5—H5A	119.7	C13—C14—H14A	119.9
C5—C6—C1	119.58 (17)	C14—C15—C16	119.79 (17)
C5—C6—H6A	120.2	C14—C15—H15A	120.1
C1—C6—H6A	120.2	C16—C15—H15A	120.1
O1—C7—C8	122.07 (15)	C15—C16—C17	120.44 (18)
O1—C7—C1	117.75 (15)	C15—C16—H16A	119.8
C8—C7—C1	120.17 (13)	C17—C16—H16A	119.8
C9—C8—C10	118.88 (15)	C12—C17—C16	119.11 (17)
C9—C8—C7	121.80 (14)	C12—C17—H17A	120.4
C10—C8—C7	118.79 (14)	C16—C17—H17A	120.4
C6—C1—C2—C3	−0.8 (2)	C12—N1—C9—S1	−9.1 (2)
C7—C1—C2—C3	−178.16 (16)	C10—C8—C9—N1	162.52 (16)
C1—C2—C3—C4	1.2 (3)	C7—C8—C9—N1	−9.0 (2)
C2—C3—C4—C5	−0.5 (3)	C10—C8—C9—S1	−15.0 (2)
C3—C4—C5—C6	−0.7 (3)	C7—C8—C9—S1	173.43 (12)
C4—C5—C6—C1	1.0 (3)	C11—S1—C9—N1	139.77 (13)
C2—C1—C6—C5	−0.3 (2)	C11—S1—C9—C8	−42.56 (16)
C7—C1—C6—C5	176.88 (15)	C9—N1—C12—C13	−87.4 (2)
C2—C1—C7—O1	39.4 (2)	C9—N1—C12—C17	94.4 (2)
C6—C1—C7—O1	−137.81 (18)	C17—C12—C13—C14	−1.2 (3)
C2—C1—C7—C8	−139.89 (16)	N1—C12—C13—C14	−179.41 (19)
C6—C1—C7—C8	42.9 (2)	C12—C13—C14—C15	0.2 (3)
O1—C7—C8—C9	8.1 (3)	C13—C14—C15—C16	0.2 (3)
C1—C7—C8—C9	−172.59 (14)	C14—C15—C16—C17	0.2 (3)
O1—C7—C8—C10	−163.40 (17)	C13—C12—C17—C16	1.6 (3)
C1—C7—C8—C10	15.9 (2)	N1—C12—C17—C16	179.83 (18)
C12—N1—C9—C8	173.11 (16)	C15—C16—C17—C12	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.91 (3)	1.86 (3)	2.610 (2)	137 (2)
C11—H11B···N2	0.96	2.60	3.372 (2)	138
C17—H17A···Cg1i	0.93	2.91	3.690 (2)	143

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
N1—H1N1⋯O1	0.91 (3)	1.86 (3)	2.610 (2)	137 (2)
C11—H11B⋯N2	0.96	2.60	3.372 (2)	138
C17—H17A⋯Cg1i	0.93	2.91	3.690 (2)	143

Symmetry code: (i) .