(2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-[4-(methyl-sulfan-yl)phen-yl]prop-2-en-1-one.

In the title compound, C(29)H(22)F(2)O(2)S, the central benzene ring makes dihedral angles of 45.83 (7), 38.90 (7) and 55.50 (7)° with the two fluoro-substituted benzene rings and the methyl-sulfanyl-substituted benzene ring, respectively. In the crystal, C-H⋯O contacts connect the mol-ecules into layers lying perpendicular to the c axis. In addition, π-π stacking inter-actions between one of the fluoro-phenyl groups [centroid-centroid distances = 3.681 (1) and 3.818 (1) Å] are observed.

Related literature

For the pharmacological importance of terphenyls, see: Liu (2006 ▶); Gill & Steglich (1987 ▶). For related structures and background to terphenyl chalcones, see: Fun et al. (2011 ▶); Fun, Loh et al. (2012 ▶); Fun, Hemamalini et al. (2012 ▶); Samshuddin et al. (2012 ▶).

Experimental

Crystal data

C29H22F2O2S

M = 472.53

Triclinic,

a = 6.9341 (3) Å

b = 11.4440 (4) Å

c = 15.4719 (5) Å

α = 89.611 (3)°

β = 84.738 (3)°

γ = 74.981 (3)°

V = 1180.63 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.743, T max = 1.000

17866 measured reflections

4637 independent reflections

2891 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.142

S = 1.06

4637 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030139/gk2507sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030139/gk2507Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030139/gk2507Isup3.cml

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

C29H22F2O2S	Z = 2
Mr = 472.53	F(000) = 492
Triclinic, P1	Dx = 1.329 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9341 (3) Å	Cell parameters from 6989 reflections
b = 11.4440 (4) Å	θ = 3.4–29.0°
c = 15.4719 (5) Å	µ = 0.18 mm−1
α = 89.611 (3)°	T = 293 K
β = 84.738 (3)°	Block, colourless
γ = 74.981 (3)°	0.3 × 0.2 × 0.1 mm
V = 1180.63 (8) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4637 independent reflections
Radiation source: fine-focus sealed tube	2891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.743, Tmax = 1.000	l = −19→18
17866 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.050P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
4637 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.40890 (12)	0.64035 (8)	0.44889 (6)	0.0889 (3)
O1	0.7122 (3)	0.17723 (16)	0.18542 (13)	0.0650 (5)
O2	0.3175 (2)	0.07240 (15)	0.09901 (11)	0.0553 (5)
F1	0.8319 (2)	−0.69853 (13)	−0.03117 (11)	0.0751 (5)
F2	1.3029 (2)	−0.00661 (17)	0.42397 (11)	0.0909 (6)
C1	0.5711 (3)	0.1332 (2)	0.20122 (15)	0.0442 (6)
C2	0.3756 (3)	0.2042 (2)	0.24325 (15)	0.0480 (6)
H2	0.2724	0.1664	0.2544	0.058*
C3	0.3434 (4)	0.3184 (2)	0.26524 (16)	0.0530 (6)
H3	0.4496	0.3532	0.2521	0.064*
C4	0.5921 (3)	0.00322 (19)	0.17939 (14)	0.0372 (5)
C5	0.4622 (3)	−0.0251 (2)	0.12300 (14)	0.0399 (5)
C6	0.4896 (3)	−0.1416 (2)	0.09174 (14)	0.0395 (5)
H6	0.4048	−0.1577	0.0528	0.047*
C7	0.6436 (3)	−0.2346 (2)	0.11840 (14)	0.0380 (5)
C8	0.7656 (3)	−0.2085 (2)	0.17810 (14)	0.0399 (5)
H8	0.8633	−0.2714	0.1989	0.048*
C9	0.7460 (3)	−0.0909 (2)	0.20762 (14)	0.0375 (5)
C10	0.6860 (3)	−0.3577 (2)	0.08015 (15)	0.0397 (5)
C11	0.7337 (3)	−0.4601 (2)	0.13080 (17)	0.0497 (6)
H11	0.7335	−0.4513	0.1905	0.060*
C12	0.7817 (3)	−0.5751 (2)	0.0935 (2)	0.0566 (7)
H12	0.8123	−0.6435	0.1276	0.068*
C13	0.7829 (3)	−0.5854 (2)	0.00604 (19)	0.0508 (7)
C14	0.7387 (3)	−0.4878 (2)	−0.04658 (17)	0.0508 (6)
H14	0.7423	−0.4979	−0.1064	0.061*
C15	0.6882 (3)	−0.3735 (2)	−0.00880 (16)	0.0450 (6)
H15	0.6552	−0.3060	−0.0436	0.054*
C16	0.8901 (3)	−0.0692 (2)	0.26791 (14)	0.0403 (5)
C17	1.0920 (3)	−0.1319 (2)	0.25431 (16)	0.0468 (6)
H17	1.1337	−0.1881	0.2088	0.056*
C18	1.2309 (4)	−0.1124 (2)	0.30686 (17)	0.0551 (7)
H18	1.3654	−0.1544	0.2974	0.066*
C19	1.1654 (4)	−0.0298 (3)	0.37315 (18)	0.0591 (7)
C20	0.9699 (4)	0.0323 (3)	0.38994 (17)	0.0588 (7)
H20	0.9303	0.0883	0.4356	0.071*
C21	0.8313 (4)	0.0105 (2)	0.33757 (16)	0.0502 (6)
H21	0.6964	0.0501	0.3495	0.060*
C22	0.1589 (4)	0.3980 (2)	0.30834 (16)	0.0508 (6)
C23	−0.0195 (4)	0.3617 (2)	0.32391 (18)	0.0600 (7)
H23	−0.0242	0.2856	0.3051	0.072*
C24	−0.1874 (4)	0.4378 (3)	0.36682 (18)	0.0637 (8)
H24	−0.3044	0.4124	0.3764	0.076*
C25	−0.1853 (4)	0.5513 (2)	0.39591 (17)	0.0582 (7)
C26	−0.0107 (4)	0.5880 (3)	0.3797 (2)	0.0715 (8)
H26	−0.0070	0.6646	0.3979	0.086*
C27	0.1582 (4)	0.5120 (2)	0.3369 (2)	0.0682 (8)
H27	0.2743	0.5383	0.3270	0.082*
C28	−0.3394 (5)	0.7674 (3)	0.4870 (2)	0.0957 (11)
H28A	−0.2290	0.7409	0.5218	0.144*
H28B	−0.4512	0.8188	0.5213	0.144*
H28C	−0.3002	0.8116	0.4384	0.144*
C29	0.1591 (3)	0.0508 (2)	0.05390 (17)	0.0576 (7)
H29A	0.2128	0.0144	−0.0018	0.086*
H29B	0.0621	0.1261	0.0463	0.086*
H29C	0.0959	−0.0027	0.0870	0.086*

	U11	U22	U33	U12	U13	U23
S1	0.0759 (6)	0.0692 (6)	0.1064 (7)	0.0019 (4)	0.0114 (5)	−0.0202 (5)
O1	0.0592 (11)	0.0438 (11)	0.0934 (14)	−0.0207 (9)	0.0062 (10)	0.0036 (10)
O2	0.0536 (10)	0.0405 (10)	0.0678 (12)	0.0007 (8)	−0.0225 (8)	−0.0004 (9)
F1	0.0679 (10)	0.0393 (9)	0.1142 (14)	−0.0066 (7)	−0.0084 (9)	−0.0239 (9)
F2	0.0848 (12)	0.1172 (16)	0.0862 (13)	−0.0433 (11)	−0.0390 (10)	−0.0052 (11)
C1	0.0496 (14)	0.0346 (14)	0.0472 (14)	−0.0087 (11)	−0.0048 (11)	0.0046 (11)
C2	0.0528 (14)	0.0345 (14)	0.0549 (15)	−0.0090 (11)	−0.0030 (11)	0.0009 (12)
C3	0.0559 (15)	0.0407 (15)	0.0605 (17)	−0.0097 (12)	−0.0042 (12)	−0.0028 (13)
C4	0.0384 (12)	0.0306 (12)	0.0412 (13)	−0.0082 (9)	0.0016 (9)	−0.0017 (10)
C5	0.0348 (11)	0.0359 (13)	0.0457 (14)	−0.0037 (10)	−0.0034 (10)	0.0025 (11)
C6	0.0364 (12)	0.0385 (14)	0.0431 (13)	−0.0082 (10)	−0.0059 (10)	0.0010 (11)
C7	0.0358 (12)	0.0339 (13)	0.0438 (13)	−0.0090 (9)	−0.0010 (9)	0.0009 (10)
C8	0.0375 (12)	0.0317 (13)	0.0478 (14)	−0.0035 (9)	−0.0064 (10)	0.0022 (11)
C9	0.0349 (11)	0.0361 (13)	0.0403 (13)	−0.0083 (9)	0.0010 (9)	0.0004 (10)
C10	0.0312 (11)	0.0338 (13)	0.0546 (15)	−0.0082 (9)	−0.0066 (10)	−0.0004 (11)
C11	0.0509 (14)	0.0405 (15)	0.0583 (16)	−0.0124 (11)	−0.0060 (11)	0.0016 (13)
C12	0.0520 (15)	0.0340 (15)	0.084 (2)	−0.0098 (11)	−0.0099 (13)	0.0075 (14)
C13	0.0366 (13)	0.0338 (14)	0.081 (2)	−0.0063 (10)	−0.0062 (12)	−0.0131 (14)
C14	0.0450 (14)	0.0481 (16)	0.0590 (16)	−0.0112 (11)	−0.0055 (11)	−0.0122 (13)
C15	0.0420 (13)	0.0377 (14)	0.0559 (16)	−0.0096 (10)	−0.0097 (11)	0.0001 (12)
C16	0.0423 (12)	0.0379 (13)	0.0424 (13)	−0.0138 (10)	−0.0034 (10)	0.0026 (11)
C17	0.0427 (13)	0.0485 (15)	0.0499 (15)	−0.0131 (11)	−0.0036 (10)	−0.0011 (12)
C18	0.0433 (14)	0.0634 (18)	0.0608 (17)	−0.0160 (12)	−0.0108 (12)	0.0088 (14)
C19	0.0631 (17)	0.068 (2)	0.0560 (17)	−0.0301 (15)	−0.0213 (13)	0.0079 (15)
C20	0.0731 (18)	0.0593 (18)	0.0465 (15)	−0.0198 (14)	−0.0109 (13)	−0.0065 (13)
C21	0.0500 (14)	0.0500 (16)	0.0493 (15)	−0.0111 (11)	−0.0033 (11)	−0.0011 (12)
C22	0.0557 (15)	0.0361 (15)	0.0570 (16)	−0.0041 (11)	−0.0084 (12)	−0.0019 (12)
C23	0.0672 (17)	0.0413 (16)	0.0694 (19)	−0.0096 (13)	−0.0077 (14)	−0.0066 (14)
C24	0.0596 (16)	0.0539 (18)	0.074 (2)	−0.0105 (14)	−0.0006 (14)	−0.0030 (15)
C25	0.0642 (17)	0.0488 (17)	0.0535 (17)	−0.0005 (13)	−0.0042 (12)	−0.0051 (13)
C26	0.078 (2)	0.0461 (18)	0.087 (2)	−0.0097 (15)	−0.0068 (16)	−0.0193 (16)
C27	0.0633 (17)	0.0477 (17)	0.091 (2)	−0.0124 (14)	0.0013 (15)	−0.0157 (16)
C28	0.117 (3)	0.065 (2)	0.090 (3)	−0.0009 (19)	0.004 (2)	−0.020 (2)
C29	0.0407 (13)	0.0608 (18)	0.0663 (18)	−0.0009 (12)	−0.0153 (12)	0.0047 (14)

S1—C25	1.753 (3)	C14—C15	1.382 (3)
S1—C28	1.767 (3)	C14—H14	0.9300
O1—C1	1.217 (3)	C15—H15	0.9300
O2—C5	1.368 (3)	C16—C21	1.378 (3)
O2—C29	1.428 (3)	C16—C17	1.395 (3)
F1—C13	1.367 (3)	C17—C18	1.377 (3)
F2—C19	1.367 (3)	C17—H17	0.9300
C1—C2	1.482 (3)	C18—C19	1.363 (4)
C1—C4	1.494 (3)	C18—H18	0.9300
C2—C3	1.310 (3)	C19—C20	1.360 (4)
C2—H2	0.9300	C20—C21	1.383 (3)
C3—C22	1.470 (3)	C20—H20	0.9300
C3—H3	0.9300	C21—H21	0.9300
C4—C9	1.404 (3)	C22—C27	1.378 (3)
C4—C5	1.406 (3)	C22—C23	1.404 (3)
C5—C6	1.381 (3)	C23—C24	1.377 (3)
C6—C7	1.389 (3)	C23—H23	0.9300
C6—H6	0.9300	C24—C25	1.381 (4)
C7—C8	1.392 (3)	C24—H24	0.9300
C7—C10	1.479 (3)	C25—C26	1.382 (4)
C8—C9	1.393 (3)	C26—C27	1.380 (4)
C8—H8	0.9300	C26—H26	0.9300
C9—C16	1.494 (3)	C27—H27	0.9300
C10—C15	1.387 (3)	C28—H28A	0.9600
C10—C11	1.389 (3)	C28—H28B	0.9600
C11—C12	1.387 (3)	C28—H28C	0.9600
C11—H11	0.9300	C29—H29A	0.9600
C12—C13	1.358 (4)	C29—H29B	0.9600
C12—H12	0.9300	C29—H29C	0.9600
C13—C14	1.364 (3)
C25—S1—C28	103.53 (15)	C21—C16—C9	122.5 (2)
C5—O2—C29	118.40 (19)	C17—C16—C9	119.5 (2)
O1—C1—C2	122.0 (2)	C18—C17—C16	121.4 (2)
O1—C1—C4	120.2 (2)	C18—C17—H17	119.3
C2—C1—C4	117.7 (2)	C16—C17—H17	119.3
C3—C2—C1	122.1 (2)	C19—C18—C17	118.0 (2)
C3—C2—H2	118.9	C19—C18—H18	121.0
C1—C2—H2	118.9	C17—C18—H18	121.0
C2—C3—C22	127.5 (2)	C20—C19—C18	122.9 (2)
C2—C3—H3	116.2	C20—C19—F2	118.5 (3)
C22—C3—H3	116.2	C18—C19—F2	118.5 (2)
C9—C4—C5	118.7 (2)	C19—C20—C21	118.5 (2)
C9—C4—C1	122.53 (19)	C19—C20—H20	120.7
C5—C4—C1	118.6 (2)	C21—C20—H20	120.7
O2—C5—C6	124.1 (2)	C16—C21—C20	121.0 (2)
O2—C5—C4	114.4 (2)	C16—C21—H21	119.5
C6—C5—C4	121.4 (2)	C20—C21—H21	119.5
C5—C6—C7	120.0 (2)	C27—C22—C23	117.6 (2)
C5—C6—H6	120.0	C27—C22—C3	120.0 (2)
C7—C6—H6	120.0	C23—C22—C3	122.4 (2)
C6—C7—C8	118.8 (2)	C24—C23—C22	120.6 (2)
C6—C7—C10	120.8 (2)	C24—C23—H23	119.7
C8—C7—C10	120.2 (2)	C22—C23—H23	119.7
C7—C8—C9	122.0 (2)	C23—C24—C25	121.2 (3)
C7—C8—H8	119.0	C23—C24—H24	119.4
C9—C8—H8	119.0	C25—C24—H24	119.4
C8—C9—C4	118.9 (2)	C24—C25—C26	118.4 (2)
C8—C9—C16	118.8 (2)	C24—C25—S1	117.0 (2)
C4—C9—C16	122.3 (2)	C26—C25—S1	124.6 (2)
C15—C10—C11	118.3 (2)	C27—C26—C25	120.7 (3)
C15—C10—C7	120.1 (2)	C27—C26—H26	119.7
C11—C10—C7	121.5 (2)	C25—C26—H26	119.7
C12—C11—C10	120.9 (2)	C22—C27—C26	121.6 (3)
C12—C11—H11	119.5	C22—C27—H27	119.2
C10—C11—H11	119.5	C26—C27—H27	119.2
C13—C12—C11	118.4 (3)	S1—C28—H28A	109.5
C13—C12—H12	120.8	S1—C28—H28B	109.5
C11—C12—H12	120.8	H28A—C28—H28B	109.5
C12—C13—C14	122.9 (2)	S1—C28—H28C	109.5
C12—C13—F1	118.7 (2)	H28A—C28—H28C	109.5
C14—C13—F1	118.4 (2)	H28B—C28—H28C	109.5
C13—C14—C15	118.3 (2)	O2—C29—H29A	109.5
C13—C14—H14	120.9	O2—C29—H29B	109.5
C15—C14—H14	120.9	H29A—C29—H29B	109.5
C14—C15—C10	121.2 (2)	O2—C29—H29C	109.5
C14—C15—H15	119.4	H29A—C29—H29C	109.5
C10—C15—H15	119.4	H29B—C29—H29C	109.5
C21—C16—C17	118.1 (2)
O1—C1—C2—C3	0.4 (4)	C12—C13—C14—C15	−0.7 (3)
C4—C1—C2—C3	179.6 (2)	F1—C13—C14—C15	179.68 (18)
C1—C2—C3—C22	−178.9 (2)	C13—C14—C15—C10	1.2 (3)
O1—C1—C4—C9	53.5 (3)	C11—C10—C15—C14	−0.7 (3)
C2—C1—C4—C9	−125.7 (2)	C7—C10—C15—C14	176.28 (19)
O1—C1—C4—C5	−121.5 (2)	C8—C9—C16—C21	−140.0 (2)
C2—C1—C4—C5	59.3 (3)	C4—C9—C16—C21	40.3 (3)
C29—O2—C5—C6	13.8 (3)	C8—C9—C16—C17	39.7 (3)
C29—O2—C5—C4	−169.76 (19)	C4—C9—C16—C17	−140.0 (2)
C9—C4—C5—O2	−179.93 (18)	C21—C16—C17—C18	−2.1 (4)
C1—C4—C5—O2	−4.7 (3)	C9—C16—C17—C18	178.2 (2)
C9—C4—C5—C6	−3.4 (3)	C16—C17—C18—C19	0.1 (4)
C1—C4—C5—C6	171.84 (19)	C17—C18—C19—C20	0.9 (4)
O2—C5—C6—C7	178.6 (2)	C17—C18—C19—F2	−177.8 (2)
C4—C5—C6—C7	2.4 (3)	C18—C19—C20—C21	0.2 (4)
C5—C6—C7—C8	1.3 (3)	F2—C19—C20—C21	178.9 (2)
C5—C6—C7—C10	−174.82 (19)	C17—C16—C21—C20	3.2 (4)
C6—C7—C8—C9	−4.1 (3)	C9—C16—C21—C20	−177.2 (2)
C10—C7—C8—C9	172.08 (19)	C19—C20—C21—C16	−2.3 (4)
C7—C8—C9—C4	3.1 (3)	C2—C3—C22—C27	171.7 (3)
C7—C8—C9—C16	−176.63 (19)	C2—C3—C22—C23	−6.8 (4)
C5—C4—C9—C8	0.7 (3)	C27—C22—C23—C24	−0.5 (4)
C1—C4—C9—C8	−174.35 (19)	C3—C22—C23—C24	178.1 (2)
C5—C4—C9—C16	−179.65 (19)	C22—C23—C24—C25	−0.2 (4)
C1—C4—C9—C16	5.3 (3)	C23—C24—C25—C26	1.0 (4)
C6—C7—C10—C15	43.8 (3)	C23—C24—C25—S1	179.5 (2)
C8—C7—C10—C15	−132.3 (2)	C28—S1—C25—C24	173.2 (2)
C6—C7—C10—C11	−139.4 (2)	C28—S1—C25—C26	−8.4 (3)
C8—C7—C10—C11	44.6 (3)	C24—C25—C26—C27	−1.1 (4)
C15—C10—C11—C12	−0.2 (3)	S1—C25—C26—C27	−179.5 (2)
C7—C10—C11—C12	−177.2 (2)	C23—C22—C27—C26	0.4 (4)
C10—C11—C12—C13	0.7 (3)	C3—C22—C27—C26	−178.2 (3)
C11—C12—C13—C14	−0.2 (4)	C25—C26—C27—C22	0.4 (5)
C11—C12—C13—F1	179.42 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.93	2.47	3.289 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.47	3.289 (3)	147

Symmetry code: (i) .