(E)-3-[5-(Di-phenyl-amino)-thio-phen-2-yl]-1-(pyridin-3-yl)prop-2-en-1-one.

In the title compound, C24H18N2OS, the pyridine and the two phenyl rings are oriented at dihedral angles of 10.1 (5), 71.7 (6) and 68.7 (5)°, respectively, to the central thio-phene ring. In the crystal, pairs of weak C-H⋯O hydrogen bonds link inversion-related mol-ecules, forming dimers. The dimers are linked by further weak C-H⋯O hydrogen bonds, forming chains running along the a-axis direction.

Related literature

For background to the title compound, see: Wan & Mak (2011 ▶). For related compounds, see: Encinas (2002 ▶); Feng et al. (2012 ▶).

Experimental

Crystal data

C24H18N2OS

M = 382.46

Monoclinic,

a = 10.976 (5) Å

b = 18.029 (5) Å

c = 9.697 (5) Å

β = 90.728 (5)°

V = 1918.7 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

13536 measured reflections

3388 independent reflections

2517 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.138

S = 0.95

3388 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536813021946/xu5725sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021946/xu5725Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021946/xu5725Isup3.cml

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

C24H18N2OS	F(000) = 800
Mr = 382.46	Dx = 1.324 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3272 reflections
a = 10.976 (5) Å	θ = 2.2–22.8°
b = 18.029 (5) Å	µ = 0.19 mm−1
c = 9.697 (5) Å	T = 293 K
β = 90.728 (5)°	Block, red
V = 1918.7 (14) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2517 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
phi and ω scans	h = −13→13
13536 measured reflections	k = −21→21
3388 independent reflections	l = −11→11

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3388 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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	0.39364 (5)	0.13546 (3)	0.84763 (5)	0.0520 (2)
O1	0.80534 (14)	0.06367 (10)	1.13966 (15)	0.0628 (4)
N1	0.23384 (15)	0.12744 (10)	0.63004 (17)	0.0518 (5)
C18	0.61524 (18)	0.11137 (11)	1.0700 (2)	0.0471 (5)
H18	0.5526	0.1439	1.0917	0.057*
C14	0.41913 (19)	0.04995 (12)	0.6381 (2)	0.0483 (5)
H14	0.4065	0.0256	0.5546	0.058*
C7	0.13189 (17)	0.15100 (11)	0.70872 (19)	0.0438 (5)
C20	0.70392 (18)	0.12875 (11)	1.3133 (2)	0.0431 (5)
C13	0.33940 (17)	0.10074 (11)	0.69095 (19)	0.0428 (5)
C15	0.52143 (18)	0.03859 (11)	0.7228 (2)	0.0480 (5)
H15	0.5835	0.0058	0.7003	0.058*
C19	0.71424 (18)	0.09932 (11)	1.1691 (2)	0.0448 (5)
C16	0.52275 (17)	0.07951 (11)	0.8412 (2)	0.0428 (5)
C1	0.22037 (18)	0.12040 (11)	0.4829 (2)	0.0444 (5)
C2	0.3006 (2)	0.15559 (14)	0.3977 (2)	0.0576 (6)
H2	0.3623	0.1851	0.4348	0.069*
C12	0.08974 (19)	0.10913 (13)	0.8175 (2)	0.0511 (5)
H12	0.1278	0.0647	0.8410	0.061*
C17	0.61310 (18)	0.07655 (11)	0.9487 (2)	0.0445 (5)
H17	0.6796	0.0461	0.9316	0.053*
N2	0.60796 (19)	0.20514 (11)	1.4845 (2)	0.0666 (6)
C8	0.0729 (2)	0.21623 (12)	0.6732 (2)	0.0561 (6)
H8	0.1001	0.2440	0.5988	0.067*
C11	−0.0099 (2)	0.13381 (15)	0.8915 (2)	0.0644 (7)
H11	−0.0384	0.1059	0.9650	0.077*
C21	0.7850 (2)	0.10299 (13)	1.4133 (2)	0.0559 (6)
H21	0.8449	0.0689	1.3901	0.067*
C6	0.1268 (2)	0.07803 (13)	0.4276 (3)	0.0601 (6)
H6	0.0709	0.0552	0.4850	0.072*
C24	0.61859 (19)	0.17992 (12)	1.3549 (2)	0.0541 (5)
H24	0.5646	0.1983	1.2885	0.065*
C9	−0.0253 (2)	0.24017 (14)	0.7469 (3)	0.0668 (7)
H9	−0.0641	0.2842	0.7225	0.080*
C22	0.7765 (3)	0.12783 (14)	1.5463 (3)	0.0663 (7)
H22	0.8298	0.1110	1.6147	0.080*
C10	−0.0670 (2)	0.19950 (16)	0.8567 (3)	0.0686 (7)
H10	−0.1331	0.2162	0.9071	0.082*
C5	0.1175 (3)	0.07000 (15)	0.2857 (3)	0.0767 (8)
H5	0.0553	0.0412	0.2476	0.092*
C4	0.1995 (3)	0.10438 (18)	0.2009 (3)	0.0751 (8)
H4	0.1934	0.0985	0.1058	0.090*
C3	0.2895 (2)	0.14712 (17)	0.2569 (2)	0.0729 (8)
H3	0.3443	0.1709	0.1993	0.087*
C23	0.6874 (2)	0.17810 (14)	1.5755 (3)	0.0675 (7)
H23	0.6821	0.1946	1.6660	0.081*

	U11	U22	U33	U12	U13	U23
S1	0.0452 (4)	0.0707 (4)	0.0401 (3)	0.0160 (3)	−0.0087 (2)	−0.0122 (2)
O1	0.0445 (9)	0.0911 (12)	0.0526 (10)	0.0187 (8)	−0.0041 (7)	−0.0018 (8)
N1	0.0342 (9)	0.0881 (13)	0.0330 (9)	0.0109 (9)	−0.0021 (7)	−0.0039 (8)
C18	0.0383 (12)	0.0567 (12)	0.0462 (13)	0.0059 (9)	−0.0039 (9)	0.0020 (9)
C14	0.0432 (12)	0.0627 (13)	0.0389 (11)	0.0028 (9)	−0.0020 (9)	−0.0086 (9)
C7	0.0338 (11)	0.0625 (13)	0.0349 (11)	0.0022 (9)	−0.0034 (8)	−0.0073 (9)
C20	0.0379 (11)	0.0476 (11)	0.0438 (11)	−0.0084 (9)	−0.0041 (9)	0.0020 (9)
C13	0.0345 (11)	0.0594 (12)	0.0346 (11)	0.0007 (9)	−0.0002 (8)	0.0002 (9)
C15	0.0419 (12)	0.0579 (12)	0.0441 (12)	0.0104 (9)	0.0013 (9)	−0.0041 (9)
C19	0.0366 (11)	0.0519 (11)	0.0457 (12)	−0.0003 (9)	−0.0013 (9)	0.0059 (9)
C16	0.0364 (11)	0.0524 (11)	0.0396 (11)	0.0035 (8)	−0.0020 (9)	0.0011 (9)
C1	0.0374 (11)	0.0597 (12)	0.0360 (11)	0.0080 (9)	−0.0041 (9)	−0.0016 (9)
C2	0.0415 (12)	0.0846 (16)	0.0466 (13)	−0.0002 (11)	−0.0008 (10)	0.0028 (11)
C12	0.0446 (12)	0.0659 (13)	0.0426 (12)	0.0064 (10)	−0.0030 (9)	−0.0026 (10)
C17	0.0363 (11)	0.0527 (12)	0.0444 (12)	0.0044 (9)	−0.0013 (9)	0.0060 (9)
N2	0.0664 (14)	0.0705 (13)	0.0630 (14)	−0.0058 (10)	0.0013 (11)	−0.0172 (10)
C8	0.0509 (13)	0.0625 (14)	0.0547 (13)	0.0030 (11)	−0.0055 (10)	−0.0002 (10)
C11	0.0512 (15)	0.1042 (19)	0.0378 (12)	−0.0055 (13)	0.0062 (11)	−0.0059 (12)
C21	0.0513 (13)	0.0656 (14)	0.0504 (14)	0.0010 (11)	−0.0105 (10)	−0.0023 (11)
C6	0.0519 (13)	0.0729 (15)	0.0551 (14)	−0.0091 (11)	−0.0102 (11)	0.0015 (11)
C24	0.0448 (12)	0.0574 (13)	0.0600 (15)	−0.0023 (10)	−0.0046 (10)	−0.0020 (11)
C9	0.0579 (15)	0.0697 (15)	0.0725 (17)	0.0199 (12)	−0.0076 (13)	−0.0161 (13)
C22	0.0708 (17)	0.0762 (16)	0.0513 (15)	−0.0045 (13)	−0.0187 (12)	−0.0019 (12)
C10	0.0450 (13)	0.104 (2)	0.0563 (15)	0.0204 (13)	−0.0027 (11)	−0.0312 (14)
C5	0.0746 (18)	0.0893 (19)	0.0654 (17)	0.0030 (15)	−0.0307 (15)	−0.0209 (14)
C4	0.0682 (18)	0.119 (2)	0.0377 (13)	0.0341 (16)	−0.0075 (13)	−0.0104 (14)
C3	0.0517 (15)	0.123 (2)	0.0440 (14)	0.0178 (14)	0.0038 (12)	0.0117 (14)
C23	0.0771 (18)	0.0750 (16)	0.0503 (14)	−0.0212 (14)	0.0000 (13)	−0.0149 (12)

S1—C13	1.741 (2)	C12—H12	0.9300
S1—C16	1.741 (2)	C17—H17	0.9300
O1—C19	1.226 (2)	N2—C23	1.325 (3)
N1—C13	1.380 (3)	N2—C24	1.343 (3)
N1—C7	1.427 (2)	C8—C9	1.371 (3)
N1—C1	1.439 (3)	C8—H8	0.9300
C18—C17	1.333 (3)	C11—C10	1.380 (4)
C18—C19	1.458 (3)	C11—H11	0.9300
C18—H18	0.9300	C21—C22	1.369 (3)
C14—C13	1.371 (3)	C21—H21	0.9300
C14—C15	1.398 (3)	C6—C5	1.387 (4)
C14—H14	0.9300	C6—H6	0.9300
C7—C12	1.382 (3)	C24—H24	0.9300
C7—C8	1.384 (3)	C9—C10	1.376 (4)
C20—C24	1.378 (3)	C9—H9	0.9300
C20—C21	1.387 (3)	C22—C23	1.365 (4)
C20—C19	1.501 (3)	C22—H22	0.9300
C15—C16	1.365 (3)	C10—H10	0.9300
C15—H15	0.9300	C5—C4	1.374 (4)
C16—C17	1.431 (3)	C5—H5	0.9300
C1—C2	1.371 (3)	C4—C3	1.361 (4)
C1—C6	1.382 (3)	C4—H4	0.9300
C2—C3	1.378 (3)	C3—H3	0.9300
C2—H2	0.9300	C23—H23	0.9300
C12—C11	1.389 (3)
C13—S1—C16	91.72 (9)	C16—C17—H17	115.5
C13—N1—C7	122.32 (17)	C23—N2—C24	115.7 (2)
C13—N1—C1	117.96 (16)	C9—C8—C7	120.4 (2)
C7—N1—C1	119.03 (16)	C9—C8—H8	119.8
C17—C18—C19	121.08 (19)	C7—C8—H8	119.8
C17—C18—H18	119.5	C10—C11—C12	120.4 (2)
C19—C18—H18	119.5	C10—C11—H11	119.8
C13—C14—C15	112.96 (18)	C12—C11—H11	119.8
C13—C14—H14	123.5	C22—C21—C20	119.9 (2)
C15—C14—H14	123.5	C22—C21—H21	120.1
C12—C7—C8	119.63 (19)	C20—C21—H21	120.1
C12—C7—N1	121.20 (19)	C1—C6—C5	119.2 (2)
C8—C7—N1	119.16 (18)	C1—C6—H6	120.4
C24—C20—C21	116.9 (2)	C5—C6—H6	120.4
C24—C20—C19	124.62 (19)	N2—C24—C20	124.6 (2)
C21—C20—C19	118.52 (19)	N2—C24—H24	117.7
C14—C13—N1	127.55 (19)	C20—C24—H24	117.7
C14—C13—S1	110.71 (15)	C8—C9—C10	120.5 (2)
N1—C13—S1	121.59 (15)	C8—C9—H9	119.8
C16—C15—C14	114.53 (18)	C10—C9—H9	119.8
C16—C15—H15	122.7	C23—C22—C21	118.0 (2)
C14—C15—H15	122.7	C23—C22—H22	121.0
O1—C19—C18	121.86 (19)	C21—C22—H22	121.0
O1—C19—C20	118.29 (18)	C9—C10—C11	119.5 (2)
C18—C19—C20	119.82 (18)	C9—C10—H10	120.2
C15—C16—C17	126.36 (19)	C11—C10—H10	120.2
C15—C16—S1	110.08 (15)	C4—C5—C6	120.4 (2)
C17—C16—S1	123.53 (15)	C4—C5—H5	119.8
C2—C1—C6	120.1 (2)	C6—C5—H5	119.8
C2—C1—N1	119.88 (19)	C3—C4—C5	119.7 (2)
C6—C1—N1	119.98 (19)	C3—C4—H4	120.2
C1—C2—C3	119.8 (2)	C5—C4—H4	120.2
C1—C2—H2	120.1	C4—C3—C2	120.8 (2)
C3—C2—H2	120.1	C4—C3—H3	119.6
C7—C12—C11	119.5 (2)	C2—C3—H3	119.6
C7—C12—H12	120.2	N2—C23—C22	125.0 (2)
C11—C12—H12	120.2	N2—C23—H23	117.5
C18—C17—C16	129.0 (2)	C22—C23—H23	117.5
C18—C17—H17	115.5
C13—N1—C7—C12	−45.5 (3)	C6—C1—C2—C3	−1.6 (3)
C1—N1—C7—C12	124.8 (2)	N1—C1—C2—C3	178.2 (2)
C13—N1—C7—C8	135.9 (2)	C8—C7—C12—C11	−1.2 (3)
C1—N1—C7—C8	−53.9 (3)	N1—C7—C12—C11	−179.87 (19)
C15—C14—C13—N1	176.09 (19)	C19—C18—C17—C16	177.90 (19)
C15—C14—C13—S1	0.6 (2)	C15—C16—C17—C18	−175.2 (2)
C7—N1—C13—C14	150.3 (2)	S1—C16—C17—C18	2.6 (3)
C1—N1—C13—C14	−20.1 (3)	C12—C7—C8—C9	1.3 (3)
C7—N1—C13—S1	−34.7 (3)	N1—C7—C8—C9	179.96 (19)
C1—N1—C13—S1	154.93 (15)	C7—C12—C11—C10	0.2 (3)
C16—S1—C13—C14	−0.95 (16)	C24—C20—C21—C22	0.9 (3)
C16—S1—C13—N1	−176.74 (17)	C19—C20—C21—C22	−178.9 (2)
C13—C14—C15—C16	0.2 (3)	C2—C1—C6—C5	1.8 (3)
C17—C18—C19—O1	8.2 (3)	N1—C1—C6—C5	−178.0 (2)
C17—C18—C19—C20	−169.57 (19)	C23—N2—C24—C20	0.6 (3)
C24—C20—C19—O1	168.2 (2)	C21—C20—C24—N2	−1.1 (3)
C21—C20—C19—O1	−12.1 (3)	C19—C20—C24—N2	178.65 (19)
C24—C20—C19—C18	−13.9 (3)	C7—C8—C9—C10	−0.3 (4)
C21—C20—C19—C18	165.80 (19)	C20—C21—C22—C23	−0.3 (4)
C14—C15—C16—C17	177.10 (19)	C8—C9—C10—C11	−0.7 (4)
C14—C15—C16—S1	−0.9 (2)	C12—C11—C10—C9	0.8 (4)
C13—S1—C16—C15	1.05 (16)	C1—C6—C5—C4	−0.7 (4)
C13—S1—C16—C17	−177.03 (18)	C6—C5—C4—C3	−0.7 (4)
C13—N1—C1—C2	−62.3 (3)	C5—C4—C3—C2	0.9 (4)
C7—N1—C1—C2	127.0 (2)	C1—C2—C3—C4	0.2 (4)
C13—N1—C1—C6	117.6 (2)	C24—N2—C23—C22	0.0 (4)
C7—N1—C1—C6	−53.1 (3)	C21—C22—C23—N2	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.54	3.410 (3)	155
C12—H12···O1ii	0.93	2.43	3.346 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.54	3.410 (3)	155
C12—H12⋯O1ii	0.93	2.43	3.346 (3)	166

Symmetry codes: (i) ; (ii) .