Crystal structure of 2-(4-chloro-phen-yl)-3-(4-meth-oxy-phen-yl)-3-(methyl-sulfanyl)-acrylo-nitrile.

In the title compound, C17H14ClNOS, the aromatic rings are inclined to one another by 64.22 (9)°. The acrylo-nitrile group (C=C-C N) is planar to within 0.003 (2) Å, with the S atom and the methyl C atom displaced from this plane by 0.2317 (6) and -0.637 (2) Å, respectively. In the crystal, mol-ecules are linked via pairs of C-H⋯π inter-actions, forming inversion dimers. There are no other significant inter-molecular inter-actions present.

Related literature

For the biological and pharmacological activities of acrylo­nitrile derivatives, see: Boëdec et al. (2008 ▶); Napolitano et al. (2001 ▶); Saczewski et al. (2004 ▶); Sommen et al. (2003 ▶). For related literature, see: Saufi & Ismail (2002 ▶); Urska et al. (2003 ▶).

Experimental

Crystal data

C17H14ClNOS

M = 315.81

Monoclinic,

a = 8.3060 (4) Å

b = 10.5048 (6) Å

c = 17.9795 (9) Å

β = 100.598 (5)°

V = 1542.00 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

6889 measured reflections

3537 independent reflections

2807 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.114

S = 1.04

3537 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814021576/su2787sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021576/su2787Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021576/su2787Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814021576/su2787fig1.tif

A view of the mol­ecular structure of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S1600536814021576/su2787fig2.tif

A view along the b axis of the crystal packing of the title compound.

CCDC reference: 1026843

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H14ClNOS	F(000) = 656
Mr = 315.81	Dx = 1.360 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3537 reflections
a = 8.3060 (4) Å	θ = 2.5–27.5°
b = 10.5048 (6) Å	µ = 0.38 mm−1
c = 17.9795 (9) Å	T = 293 K
β = 100.598 (5)°	Block, colourless
V = 1542.00 (14) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	Rint = 0.028
ω and φ scans	θmax = 27.5°, θmin = 2.5°
6889 measured reflections	h = −10→6
3537 independent reflections	k = −13→5
2807 reflections with I > 2σ(I)	l = −23→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.045P)2 + 0.3209P] where P = (Fo2 + 2Fc2)/3
3537 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl7	−0.19319 (7)	1.21573 (7)	−0.19619 (4)	0.0708 (2)
S12	0.39592 (6)	0.84311 (6)	0.00222 (3)	0.0463 (2)
O20	1.09261 (17)	0.59095 (16)	−0.06455 (9)	0.0603 (6)
N10	0.5710 (2)	0.9039 (2)	−0.25595 (10)	0.0575 (7)
C1	0.2687 (2)	1.09961 (19)	−0.18246 (10)	0.0396 (6)
C2	0.1284 (2)	1.1742 (2)	−0.19521 (11)	0.0463 (6)
C3	−0.0153 (2)	1.1236 (2)	−0.18024 (11)	0.0441 (6)
C4	−0.0223 (2)	1.0011 (2)	−0.15428 (12)	0.0496 (7)
C5	0.1178 (2)	0.9272 (2)	−0.14196 (11)	0.0452 (6)
C6	0.2658 (2)	0.97624 (18)	−0.15536 (9)	0.0347 (5)
C8	0.4179 (2)	0.89756 (18)	−0.14288 (10)	0.0346 (5)
C9	0.5065 (2)	0.8996 (2)	−0.20479 (10)	0.0401 (6)
C11	0.4820 (2)	0.83108 (18)	−0.07963 (10)	0.0353 (5)
C13	0.4464 (3)	0.6919 (2)	0.04764 (12)	0.0570 (8)
C14	0.6374 (2)	0.75884 (19)	−0.07423 (10)	0.0350 (5)
C15	0.7767 (2)	0.7996 (2)	−0.02329 (10)	0.0402 (6)
C16	0.9244 (2)	0.7402 (2)	−0.02164 (11)	0.0443 (6)
C17	0.9379 (2)	0.6388 (2)	−0.06941 (11)	0.0406 (6)
C18	0.8005 (2)	0.5942 (2)	−0.11771 (11)	0.0441 (6)
C19	0.6513 (2)	0.6553 (2)	−0.11980 (11)	0.0429 (6)
C21	1.1194 (3)	0.4982 (3)	−0.11813 (15)	0.0742 (10)
H1	0.36640	1.13300	−0.19230	0.0470*
H2	0.13140	1.25680	−0.21350	0.0550*
H4	−0.12060	0.96800	−0.14510	0.0600*
H5	0.11330	0.84410	−0.12460	0.0540*
H13A	0.40050	0.62460	0.01420	0.0860*
H13B	0.40220	0.68780	0.09330	0.0860*
H13C	0.56320	0.68250	0.05960	0.0860*
H15	0.76880	0.86710	0.00940	0.0480*
H16	1.01650	0.76820	0.01190	0.0530*
H18	0.80790	0.52400	−0.14840	0.0530*
H19	0.55900	0.62580	−0.15260	0.0520*
H21A	1.06080	0.42180	−0.11070	0.1110*
H21B	1.23430	0.47980	−0.11170	0.1110*
H21C	1.08110	0.53000	−0.16830	0.1110*

	U11	U22	U33	U12	U13	U23
Cl7	0.0571 (3)	0.0760 (5)	0.0789 (4)	0.0308 (3)	0.0114 (3)	0.0093 (4)
S12	0.0507 (3)	0.0523 (3)	0.0385 (3)	0.0136 (2)	0.0150 (2)	0.0035 (2)
O20	0.0451 (8)	0.0666 (11)	0.0699 (10)	0.0192 (7)	0.0125 (7)	−0.0035 (9)
N10	0.0579 (11)	0.0707 (14)	0.0479 (10)	0.0082 (10)	0.0199 (8)	0.0068 (10)
C1	0.0436 (10)	0.0401 (11)	0.0362 (9)	−0.0011 (8)	0.0104 (8)	0.0014 (9)
C2	0.0594 (12)	0.0383 (11)	0.0421 (10)	0.0073 (9)	0.0120 (9)	0.0045 (9)
C3	0.0447 (10)	0.0491 (12)	0.0376 (10)	0.0149 (9)	0.0049 (8)	−0.0006 (9)
C4	0.0348 (9)	0.0585 (14)	0.0548 (12)	0.0010 (9)	0.0065 (8)	0.0081 (11)
C5	0.0393 (10)	0.0412 (12)	0.0532 (11)	−0.0006 (8)	0.0033 (8)	0.0103 (10)
C6	0.0369 (9)	0.0369 (10)	0.0293 (8)	0.0019 (8)	0.0033 (7)	−0.0004 (8)
C8	0.0344 (9)	0.0353 (10)	0.0336 (9)	−0.0007 (7)	0.0051 (7)	−0.0027 (8)
C9	0.0374 (9)	0.0437 (12)	0.0377 (10)	0.0035 (8)	0.0033 (8)	0.0013 (9)
C11	0.0360 (9)	0.0346 (10)	0.0351 (9)	−0.0002 (7)	0.0064 (7)	−0.0039 (8)
C13	0.0608 (13)	0.0651 (16)	0.0479 (12)	0.0059 (11)	0.0171 (10)	0.0161 (11)
C14	0.0368 (9)	0.0365 (10)	0.0321 (8)	0.0022 (7)	0.0078 (7)	0.0015 (8)
C15	0.0423 (10)	0.0408 (11)	0.0370 (9)	−0.0008 (8)	0.0063 (8)	−0.0078 (9)
C16	0.0358 (9)	0.0521 (13)	0.0437 (10)	−0.0014 (9)	0.0036 (8)	−0.0044 (10)
C17	0.0405 (10)	0.0420 (12)	0.0409 (10)	0.0071 (8)	0.0118 (8)	0.0077 (9)
C18	0.0552 (11)	0.0366 (11)	0.0405 (10)	0.0078 (9)	0.0091 (9)	−0.0052 (9)
C19	0.0434 (10)	0.0434 (12)	0.0396 (10)	0.0022 (9)	0.0013 (8)	−0.0049 (9)
C21	0.0776 (17)	0.0797 (19)	0.0691 (15)	0.0403 (15)	0.0239 (13)	0.0036 (15)

Cl7—C3	1.745 (2)	C15—C16	1.372 (3)
S12—C11	1.7550 (18)	C16—C17	1.386 (3)
S12—C13	1.800 (2)	C17—C18	1.383 (3)
O20—C17	1.368 (2)	C18—C19	1.390 (3)
O20—C21	1.416 (3)	C1—H1	0.9300
N10—C9	1.147 (2)	C2—H2	0.9300
C1—C2	1.388 (3)	C4—H4	0.9300
C1—C6	1.386 (3)	C5—H5	0.9300
C2—C3	1.378 (3)	C13—H13A	0.9600
C3—C4	1.374 (3)	C13—H13B	0.9600
C4—C5	1.382 (3)	C13—H13C	0.9600
C5—C6	1.394 (2)	C15—H15	0.9300
C6—C8	1.492 (2)	C16—H16	0.9300
C8—C9	1.443 (2)	C18—H18	0.9300
C8—C11	1.357 (3)	C19—H19	0.9300
C11—C14	1.485 (2)	C21—H21A	0.9600
C14—C15	1.404 (2)	C21—H21B	0.9600
C14—C19	1.379 (3)	C21—H21C	0.9600
C11—S12—C13	102.71 (10)	C2—C1—H1	119.00
C17—O20—C21	118.21 (17)	C6—C1—H1	119.00
C2—C1—C6	121.16 (16)	C1—C2—H2	121.00
C1—C2—C3	118.77 (19)	C3—C2—H2	121.00
Cl7—C3—C2	119.45 (16)	C3—C4—H4	120.00
Cl7—C3—C4	119.20 (14)	C5—C4—H4	120.00
C2—C3—C4	121.34 (17)	C4—C5—H5	120.00
C3—C4—C5	119.57 (17)	C6—C5—H5	120.00
C4—C5—C6	120.52 (19)	S12—C13—H13A	109.00
C1—C6—C5	118.62 (17)	S12—C13—H13B	109.00
C1—C6—C8	120.12 (15)	S12—C13—H13C	110.00
C5—C6—C8	121.24 (17)	H13A—C13—H13B	109.00
C6—C8—C9	114.44 (15)	H13A—C13—H13C	109.00
C6—C8—C11	127.02 (16)	H13B—C13—H13C	109.00
C9—C8—C11	118.48 (16)	C14—C15—H15	120.00
N10—C9—C8	176.9 (2)	C16—C15—H15	120.00
S12—C11—C8	120.54 (14)	C15—C16—H16	120.00
S12—C11—C14	117.73 (13)	C17—C16—H16	120.00
C8—C11—C14	121.34 (16)	C17—C18—H18	120.00
C11—C14—C15	119.27 (17)	C19—C18—H18	120.00
C11—C14—C19	122.06 (16)	C14—C19—H19	119.00
C15—C14—C19	118.62 (16)	C18—C19—H19	119.00
C14—C15—C16	120.12 (18)	O20—C21—H21A	109.00
C15—C16—C17	120.68 (17)	O20—C21—H21B	110.00
O20—C17—C16	115.16 (16)	O20—C21—H21C	109.00
O20—C17—C18	124.96 (18)	H21A—C21—H21B	109.00
C16—C17—C18	119.88 (17)	H21A—C21—H21C	109.00
C17—C18—C19	119.30 (19)	H21B—C21—H21C	109.00
C14—C19—C18	121.31 (17)
C13—S12—C11—C8	152.50 (16)	C9—C8—C11—S12	170.97 (14)
C13—S12—C11—C14	−34.67 (17)	C9—C8—C11—C14	−1.6 (3)
C21—O20—C17—C18	7.3 (3)	C6—C8—C11—S12	−5.9 (3)
C21—O20—C17—C16	−172.2 (2)	C6—C8—C11—C14	−178.51 (17)
C2—C1—C6—C8	179.37 (17)	S12—C11—C14—C15	−60.3 (2)
C2—C1—C6—C5	0.9 (3)	C8—C11—C14—C19	−65.1 (3)
C6—C1—C2—C3	0.2 (3)	S12—C11—C14—C19	122.17 (18)
C1—C2—C3—Cl7	−179.80 (15)	C8—C11—C14—C15	112.5 (2)
C1—C2—C3—C4	−1.0 (3)	C11—C14—C19—C18	175.46 (18)
C2—C3—C4—C5	0.8 (3)	C15—C14—C19—C18	−2.1 (3)
Cl7—C3—C4—C5	179.59 (16)	C11—C14—C15—C16	−174.94 (18)
C3—C4—C5—C6	0.3 (3)	C19—C14—C15—C16	2.7 (3)
C4—C5—C6—C8	−179.57 (18)	C14—C15—C16—C17	−0.7 (3)
C4—C5—C6—C1	−1.1 (3)	C15—C16—C17—C18	−2.0 (3)
C1—C6—C8—C9	−47.0 (2)	C15—C16—C17—O20	177.50 (18)
C5—C6—C8—C11	−51.5 (3)	O20—C17—C18—C19	−176.86 (19)
C1—C6—C8—C11	130.0 (2)	C16—C17—C18—C19	2.6 (3)
C5—C6—C8—C9	131.45 (18)	C17—C18—C19—C14	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg1i	0.93	2.96	3.739 (2)	142

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
C15H15Cg1i	0.93	2.96	3.739(2)	142

Symmetry code: (i) .