(2E)-3-(4-Cyano-phen-yl)-1-(4,4''-difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one.

In the title compound, C(29)H(19)F(2)NO(2), the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyano-benzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluoro-benzene rings. In the crystal, C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into sheets lying parallel to the ab plane. The crystal packing also features C-H⋯π inter-actions involving the central benzene ring.

Related literature

For background to terphenyls, see: Fun, Hemamalini et al. (2011 ▶); Fun, Shahani et al. (2011 ▶); Fun et al. (2012 ▶); Betz et al. (2011 ▶). For a related structure, see: Fun, Chia et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C29H19F2NO2

M = 451.45

Triclinic,

a = 6.9656 (2) Å

b = 11.2404 (3) Å

c = 14.6014 (3) Å

α = 96.108 (1)°

β = 90.415 (1)°

γ = 104.764 (1)°

V = 1098.51 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.34 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.989

17054 measured reflections

3828 independent reflections

2982 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.112

S = 1.03

3828 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.31 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/S1600536812023124/hb6802sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023124/hb6802Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023124/hb6802Isup3.cml

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

C29H19F2NO2	Z = 2
Mr = 451.45	F(000) = 468
Triclinic, P1	Dx = 1.365 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9656 (2) Å	Cell parameters from 6297 reflections
b = 11.2404 (3) Å	θ = 2.2–30.1°
c = 14.6014 (3) Å	µ = 0.10 mm−1
α = 96.108 (1)°	T = 100 K
β = 90.415 (1)°	Plate, colourless
γ = 104.764 (1)°	0.34 × 0.20 × 0.12 mm
V = 1098.51 (5) Å3

Bruker APEXII CCD diffractometer	3828 independent reflections
Radiation source: fine-focus sealed tube	2982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.968, Tmax = 0.989	k = −13→13
17054 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0128P)2 + 2.0889P] where P = (Fo2 + 2Fc2)/3
3828 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
F1	−0.3094 (2)	1.07639 (17)	0.96874 (12)	0.0383 (5)
F2	0.1740 (2)	0.29331 (13)	0.46224 (11)	0.0282 (4)
O1	0.2862 (3)	1.22148 (17)	0.70626 (13)	0.0252 (4)
O2	0.6812 (3)	1.09304 (16)	0.60777 (12)	0.0209 (4)
N1	1.5517 (4)	1.7077 (3)	0.98443 (19)	0.0430 (7)
C1	−0.1786 (4)	1.0421 (3)	0.90947 (19)	0.0256 (6)
C2	0.0215 (4)	1.0968 (3)	0.92571 (19)	0.0235 (6)
H2A	0.0668	1.1560	0.9778	0.028*
C3	0.1545 (4)	1.0639 (2)	0.86487 (18)	0.0204 (6)
H3A	0.2927	1.1003	0.8758	0.025*
C4	0.0899 (4)	0.9781 (2)	0.78753 (17)	0.0181 (6)
C5	−0.1138 (4)	0.9222 (3)	0.77510 (18)	0.0216 (6)
H5A	−0.1603	0.8618	0.7239	0.026*
C6	−0.2491 (4)	0.9536 (3)	0.83625 (19)	0.0251 (6)
H6A	−0.3871	0.9148	0.8278	0.030*
C7	0.2004 (4)	0.4356 (2)	0.59530 (19)	0.0225 (6)
H7A	0.1618	0.3693	0.6322	0.027*
C8	0.2424 (4)	0.5575 (2)	0.63458 (18)	0.0204 (6)
H8A	0.2313	0.5749	0.6992	0.025*
C9	0.3007 (4)	0.6554 (2)	0.58073 (18)	0.0185 (6)
C10	0.3164 (4)	0.6277 (2)	0.48615 (18)	0.0205 (6)
H10A	0.3577	0.6931	0.4487	0.025*
C11	0.2725 (4)	0.5059 (2)	0.44581 (18)	0.0210 (6)
H11A	0.2813	0.4872	0.3812	0.025*
C12	0.2160 (4)	0.4130 (2)	0.50176 (19)	0.0206 (6)
C13	0.2098 (4)	0.8217 (2)	0.68521 (17)	0.0183 (6)
H13A	0.1030	0.7600	0.7052	0.022*
C14	0.2329 (4)	0.9455 (2)	0.72000 (17)	0.0179 (6)
C15	0.3935 (4)	1.0359 (2)	0.69134 (17)	0.0181 (6)
C16	0.5288 (4)	0.9990 (2)	0.63103 (17)	0.0181 (6)
C17	0.5009 (4)	0.8762 (2)	0.59581 (17)	0.0182 (6)
H17A	0.5919	0.8531	0.5537	0.022*
C18	0.3390 (4)	0.7864 (2)	0.62211 (17)	0.0188 (6)
C19	0.4204 (4)	1.1726 (2)	0.71882 (17)	0.0198 (6)
C20	0.6148 (4)	1.2424 (2)	0.76212 (17)	0.0214 (6)
H20A	0.7079	1.1977	0.7764	0.026*
C21	0.6651 (4)	1.3647 (2)	0.78190 (18)	0.0216 (6)
H21A	0.5699	1.4077	0.7672	0.026*
C22	0.8547 (4)	1.4389 (2)	0.82446 (18)	0.0216 (6)
C23	0.8852 (4)	1.5658 (3)	0.84806 (19)	0.0274 (7)
H23A	0.7825	1.6040	0.8354	0.033*
C24	1.0628 (4)	1.6374 (3)	0.8896 (2)	0.0292 (7)
H24A	1.0814	1.7239	0.9054	0.035*
C25	1.2137 (4)	1.5813 (3)	0.90810 (18)	0.0269 (7)
C26	1.1865 (4)	1.4552 (3)	0.8842 (2)	0.0295 (7)
H26A	1.2891	1.4170	0.8971	0.035*
C27	1.0109 (4)	1.3854 (3)	0.8418 (2)	0.0282 (7)
H27A	0.9950	1.2996	0.8239	0.034*
C28	1.4004 (5)	1.6533 (3)	0.9511 (2)	0.0325 (7)
C29	0.8394 (4)	1.0612 (3)	0.55730 (19)	0.0234 (6)
H29A	0.9443	1.1364	0.5510	0.035*
H29B	0.7889	1.0205	0.4960	0.035*
H29C	0.8936	1.0048	0.5903	0.035*

	U11	U22	U33	U12	U13	U23
F1	0.0321 (10)	0.0470 (12)	0.0418 (11)	0.0210 (9)	0.0180 (8)	0.0045 (9)
F2	0.0287 (9)	0.0151 (9)	0.0386 (10)	0.0049 (7)	0.0016 (7)	−0.0046 (7)
O1	0.0235 (10)	0.0234 (11)	0.0322 (11)	0.0118 (9)	0.0014 (8)	0.0047 (9)
O2	0.0191 (9)	0.0167 (10)	0.0261 (10)	0.0039 (8)	0.0083 (8)	−0.0002 (8)
N1	0.0341 (16)	0.0406 (17)	0.0495 (17)	0.0063 (13)	−0.0063 (13)	−0.0082 (14)
C1	0.0269 (15)	0.0285 (17)	0.0281 (16)	0.0161 (13)	0.0122 (12)	0.0100 (13)
C2	0.0282 (15)	0.0214 (15)	0.0230 (14)	0.0103 (12)	0.0066 (12)	0.0019 (12)
C3	0.0202 (14)	0.0192 (15)	0.0232 (14)	0.0065 (11)	0.0020 (11)	0.0044 (11)
C4	0.0190 (13)	0.0175 (14)	0.0204 (14)	0.0079 (11)	0.0023 (11)	0.0059 (11)
C5	0.0200 (14)	0.0239 (16)	0.0230 (14)	0.0078 (12)	−0.0001 (11)	0.0061 (12)
C6	0.0168 (14)	0.0296 (17)	0.0334 (16)	0.0106 (12)	0.0042 (12)	0.0124 (13)
C7	0.0206 (14)	0.0173 (15)	0.0319 (16)	0.0076 (11)	0.0036 (12)	0.0056 (12)
C8	0.0197 (14)	0.0224 (15)	0.0199 (14)	0.0067 (12)	0.0025 (11)	0.0020 (11)
C9	0.0124 (12)	0.0184 (15)	0.0241 (14)	0.0032 (11)	−0.0006 (10)	0.0014 (11)
C10	0.0186 (13)	0.0183 (15)	0.0246 (14)	0.0047 (11)	0.0007 (11)	0.0028 (12)
C11	0.0178 (14)	0.0231 (15)	0.0218 (14)	0.0069 (11)	0.0019 (11)	−0.0025 (12)
C12	0.0142 (13)	0.0150 (14)	0.0316 (16)	0.0045 (11)	0.0000 (11)	−0.0036 (12)
C13	0.0160 (13)	0.0183 (15)	0.0195 (13)	0.0023 (11)	0.0000 (11)	0.0030 (11)
C14	0.0155 (13)	0.0217 (15)	0.0169 (13)	0.0057 (11)	−0.0032 (10)	0.0025 (11)
C15	0.0174 (13)	0.0193 (15)	0.0175 (13)	0.0043 (11)	−0.0025 (11)	0.0023 (11)
C16	0.0149 (13)	0.0209 (15)	0.0184 (13)	0.0039 (11)	−0.0013 (11)	0.0031 (11)
C17	0.0171 (13)	0.0205 (15)	0.0175 (13)	0.0064 (11)	0.0008 (10)	0.0003 (11)
C18	0.0189 (13)	0.0193 (15)	0.0188 (13)	0.0060 (11)	−0.0029 (11)	0.0034 (11)
C19	0.0243 (14)	0.0209 (15)	0.0161 (13)	0.0087 (12)	0.0051 (11)	0.0027 (11)
C20	0.0257 (15)	0.0197 (16)	0.0204 (14)	0.0096 (12)	0.0013 (11)	−0.0004 (11)
C21	0.0245 (14)	0.0210 (16)	0.0214 (14)	0.0108 (12)	0.0062 (11)	−0.0005 (12)
C22	0.0278 (15)	0.0187 (15)	0.0187 (14)	0.0085 (12)	0.0067 (11)	−0.0024 (11)
C23	0.0279 (16)	0.0258 (17)	0.0288 (16)	0.0097 (13)	0.0046 (12)	−0.0029 (13)
C24	0.0333 (17)	0.0211 (16)	0.0304 (16)	0.0072 (13)	0.0086 (13)	−0.0097 (13)
C25	0.0271 (15)	0.0295 (17)	0.0204 (14)	0.0034 (13)	0.0034 (12)	−0.0039 (12)
C26	0.0292 (16)	0.0287 (17)	0.0312 (16)	0.0088 (13)	0.0007 (13)	0.0024 (13)
C27	0.0312 (16)	0.0199 (15)	0.0326 (16)	0.0057 (13)	−0.0002 (13)	0.0016 (13)
C28	0.0315 (17)	0.0304 (18)	0.0329 (17)	0.0068 (14)	0.0027 (14)	−0.0051 (14)
C29	0.0192 (14)	0.0241 (16)	0.0265 (15)	0.0047 (12)	0.0046 (11)	0.0026 (12)

F1—C1	1.360 (3)	C13—C18	1.390 (4)
F2—C12	1.364 (3)	C13—C14	1.398 (4)
O1—C19	1.221 (3)	C13—H13A	0.9500
O2—C16	1.367 (3)	C14—C15	1.406 (4)
O2—C29	1.429 (3)	C15—C16	1.403 (4)
N1—C28	1.150 (4)	C15—C19	1.510 (4)
C1—C6	1.375 (4)	C16—C17	1.385 (4)
C1—C2	1.380 (4)	C17—C18	1.394 (4)
C2—C3	1.379 (4)	C17—H17A	0.9500
C2—H2A	0.9500	C19—C20	1.479 (4)
C3—C4	1.396 (4)	C20—C21	1.328 (4)
C3—H3A	0.9500	C20—H20A	0.9500
C4—C5	1.400 (4)	C21—C22	1.464 (4)
C4—C14	1.490 (4)	C21—H21A	0.9500
C5—C6	1.387 (4)	C22—C23	1.392 (4)
C5—H5A	0.9500	C22—C27	1.404 (4)
C6—H6A	0.9500	C23—C24	1.387 (4)
C7—C12	1.373 (4)	C23—H23A	0.9500
C7—C8	1.385 (4)	C24—C25	1.395 (4)
C7—H7A	0.9500	C24—H24A	0.9500
C8—C9	1.398 (4)	C25—C26	1.387 (4)
C8—H8A	0.9500	C25—C28	1.443 (4)
C9—C10	1.394 (4)	C26—C27	1.376 (4)
C9—C18	1.488 (4)	C26—H26A	0.9500
C10—C11	1.388 (4)	C27—H27A	0.9500
C10—H10A	0.9500	C29—H29A	0.9800
C11—C12	1.374 (4)	C29—H29B	0.9800
C11—H11A	0.9500	C29—H29C	0.9800
C16—O2—C29	118.1 (2)	C14—C15—C19	122.5 (2)
F1—C1—C6	119.2 (2)	O2—C16—C17	123.8 (2)
F1—C1—C2	118.5 (3)	O2—C16—C15	115.1 (2)
C6—C1—C2	122.3 (3)	C17—C16—C15	121.1 (2)
C3—C2—C1	118.7 (3)	C16—C17—C18	120.0 (2)
C3—C2—H2A	120.7	C16—C17—H17A	120.0
C1—C2—H2A	120.7	C18—C17—H17A	120.0
C2—C3—C4	121.2 (2)	C13—C18—C17	119.1 (2)
C2—C3—H3A	119.4	C13—C18—C9	120.3 (2)
C4—C3—H3A	119.4	C17—C18—C9	120.5 (2)
C3—C4—C5	118.2 (2)	O1—C19—C20	122.5 (2)
C3—C4—C14	121.3 (2)	O1—C19—C15	120.8 (2)
C5—C4—C14	120.5 (2)	C20—C19—C15	116.7 (2)
C6—C5—C4	121.2 (3)	C21—C20—C19	123.0 (3)
C6—C5—H5A	119.4	C21—C20—H20A	118.5
C4—C5—H5A	119.4	C19—C20—H20A	118.5
C1—C6—C5	118.4 (3)	C20—C21—C22	125.6 (3)
C1—C6—H6A	120.8	C20—C21—H21A	117.2
C5—C6—H6A	120.8	C22—C21—H21A	117.2
C12—C7—C8	118.3 (3)	C23—C22—C27	118.2 (3)
C12—C7—H7A	120.9	C23—C22—C21	120.4 (2)
C8—C7—H7A	120.9	C27—C22—C21	121.5 (2)
C7—C8—C9	121.1 (2)	C24—C23—C22	121.3 (3)
C7—C8—H8A	119.5	C24—C23—H23A	119.4
C9—C8—H8A	119.5	C22—C23—H23A	119.4
C10—C9—C8	118.5 (2)	C23—C24—C25	119.4 (3)
C10—C9—C18	120.2 (2)	C23—C24—H24A	120.3
C8—C9—C18	121.2 (2)	C25—C24—H24A	120.3
C11—C10—C9	121.0 (3)	C26—C25—C24	120.1 (3)
C11—C10—H10A	119.5	C26—C25—C28	119.2 (3)
C9—C10—H10A	119.5	C24—C25—C28	120.8 (3)
C12—C11—C10	118.3 (2)	C27—C26—C25	120.0 (3)
C12—C11—H11A	120.9	C27—C26—H26A	120.0
C10—C11—H11A	120.9	C25—C26—H26A	120.0
F2—C12—C7	118.8 (2)	C26—C27—C22	121.0 (3)
F2—C12—C11	118.3 (2)	C26—C27—H27A	119.5
C7—C12—C11	122.9 (2)	C22—C27—H27A	119.5
C18—C13—C14	121.7 (2)	N1—C28—C25	177.9 (3)
C18—C13—H13A	119.1	O2—C29—H29A	109.5
C14—C13—H13A	119.1	O2—C29—H29B	109.5
C13—C14—C15	118.8 (2)	H29A—C29—H29B	109.5
C13—C14—C4	119.5 (2)	O2—C29—H29C	109.5
C15—C14—C4	121.7 (2)	H29A—C29—H29C	109.5
C16—C15—C14	119.2 (2)	H29B—C29—H29C	109.5
C16—C15—C19	118.3 (2)
F1—C1—C2—C3	−178.9 (2)	C19—C15—C16—O2	4.0 (3)
C6—C1—C2—C3	1.8 (4)	C14—C15—C16—C17	3.3 (4)
C1—C2—C3—C4	0.7 (4)	C19—C15—C16—C17	−173.4 (2)
C2—C3—C4—C5	−2.5 (4)	O2—C16—C17—C18	−178.8 (2)
C2—C3—C4—C14	177.9 (2)	C15—C16—C17—C18	−1.7 (4)
C3—C4—C5—C6	1.8 (4)	C14—C13—C18—C17	2.8 (4)
C14—C4—C5—C6	−178.6 (2)	C14—C13—C18—C9	−175.0 (2)
F1—C1—C6—C5	178.3 (2)	C16—C17—C18—C13	−1.3 (4)
C2—C1—C6—C5	−2.5 (4)	C16—C17—C18—C9	176.5 (2)
C4—C5—C6—C1	0.6 (4)	C10—C9—C18—C13	134.0 (3)
C12—C7—C8—C9	−0.5 (4)	C8—C9—C18—C13	−43.9 (4)
C7—C8—C9—C10	−0.1 (4)	C10—C9—C18—C17	−43.7 (3)
C7—C8—C9—C18	177.8 (2)	C8—C9—C18—C17	138.3 (3)
C8—C9—C10—C11	0.9 (4)	C16—C15—C19—O1	124.0 (3)
C18—C9—C10—C11	−177.1 (2)	C14—C15—C19—O1	−52.6 (4)
C9—C10—C11—C12	−1.0 (4)	C16—C15—C19—C20	−56.7 (3)
C8—C7—C12—F2	−179.7 (2)	C14—C15—C19—C20	126.7 (3)
C8—C7—C12—C11	0.5 (4)	O1—C19—C20—C21	−7.0 (4)
C10—C11—C12—F2	−179.6 (2)	C15—C19—C20—C21	173.7 (2)
C10—C11—C12—C7	0.3 (4)	C19—C20—C21—C22	−179.9 (2)
C18—C13—C14—C15	−1.2 (4)	C20—C21—C22—C23	−175.3 (3)
C18—C13—C14—C4	180.0 (2)	C20—C21—C22—C27	5.3 (4)
C3—C4—C14—C13	137.4 (3)	C27—C22—C23—C24	−1.6 (4)
C5—C4—C14—C13	−42.2 (3)	C21—C22—C23—C24	179.1 (3)
C3—C4—C14—C15	−41.4 (4)	C22—C23—C24—C25	0.0 (4)
C5—C4—C14—C15	139.0 (3)	C23—C24—C25—C26	0.6 (4)
C13—C14—C15—C16	−1.9 (4)	C23—C24—C25—C28	179.8 (3)
C4—C14—C15—C16	176.9 (2)	C24—C25—C26—C27	0.4 (4)
C13—C14—C15—C19	174.7 (2)	C28—C25—C26—C27	−178.9 (3)
C4—C14—C15—C19	−6.5 (4)	C25—C26—C27—C22	−2.0 (4)
C29—O2—C16—C17	−11.4 (3)	C23—C22—C27—C26	2.5 (4)
C29—O2—C16—C15	171.4 (2)	C21—C22—C27—C26	−178.1 (3)
C14—C15—C16—O2	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1i	0.95	2.40	3.213 (3)	143
C29—H29A···F2ii	0.98	2.54	3.447 (3)	155
C29—H29B···Cg1iii	0.98	2.75	3.521 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1i	0.95	2.40	3.213 (3)	143
C29—H29A⋯F2ii	0.98	2.54	3.447 (3)	155
C29—H29B⋯Cg1iii	0.98	2.75	3.521 (3)	136

Symmetry codes: (i) ; (ii) ; (iii) .