(2E)-3-(4-Cyano­phen­yl)-1-(4,4′′-difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Fun, H.-K.; Loh, W.-S.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812023124

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1877-o1878

doi:10.1107/S1600536812023124

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(2E)-3-(4-Cyanophenyl)-1-(4,4′′-difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § S. Samshuddin,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 May 2012; accepted 21 May 2012; online 26 May 2012)

In the title compound, C₂₉H₁₉F₂NO₂, the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyanobenzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluorobenzene rings. In the crystal, C—H⋯O and C—H⋯F hydrogen bonds link the molecules into sheets lying parallel to the ab plane. The crystal packing also features C—H⋯π interactions 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_r = 451.45
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.112
S = 1.03
3828 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x, y-1, z; (ii) x+1, y+1, z; (iii) -x+1, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023124/hb6802sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812023124/hb6802Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of terphenyl chalcones (Fun, Hemamalini et al., 2011; Fun, Shahani et al., 2011; Betz et al., 2011), the title compound is prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Fun et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C13–C18) forms dihedral angles of 56.92 (12)° with the cyanobenzene ring (C22–C28/N1) and 40.91 (12) and 44.76 (12)°, respectively, with the fluorobenzene rings (C1–C6/F1 & C7–C12/F2). Bond lengths are angles are within the normal ranges and are comparable with the related structure (Fun, Chia et al., 2011).

In the crystal packing (Fig. 2), intermolecular C7—H7A···O1 and C29—H29A···F2 hydrogen bonds (Table 1) link the molecules to form planes parallel to the ab plane. The crystal packing is further stabilized by C—H···π interactions (Table 1), involving the central benzene ring.

Related literature top

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 top

To a mixture of 1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl) ethanone (0.338 g, 0.001 mol) and 4-cyanobenzaldehyde (0.131 g, 0.001 mol) in 30 ml e thanol, 0.5 ml of 10% sodium hydroxide solution was added and stirred at 5–10°C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless plates were grown from acetone solution by slow evaporation method and yield of the compound was 78%. M.p.: 450 K.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing the plane parallel to the ab plane. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(2E)-3-(4-Cyanophenyl)-1-(4,4''-difluoro-5'-methoxy-1,1':3',1''- terphenyl-4'-yl)prop-2-en-1-one top

Crystal data top

C₂₉H₁₉F₂NO₂	Z = 2
M_r = 451.45	F(000) = 468
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0128P)² + 2.0889P] where P = (F_o² + 2F_c²)/3
3828 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₉H₁₉F₂NO₂	γ = 104.764 (1)°
M_r = 451.45	V = 1098.51 (5) Å³
Triclinic, P1	Z = 2
a = 6.9656 (2) Å	Mo Kα radiation
b = 11.2404 (3) Å	µ = 0.10 mm⁻¹
c = 14.6014 (3) Å	T = 100 K
α = 96.108 (1)°	0.34 × 0.20 × 0.12 mm
β = 90.415 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3828 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2982 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.989	R_int = 0.036
17054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
3828 reflections	Δρ_min = −0.23 e Å⁻³
308 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₉H₁₉F₂NO₂
M_r	451.45
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.9656 (2), 11.2404 (3), 14.6014 (3)
α, β, γ (°)	96.108 (1), 90.415 (1), 104.764 (1)
V (Å³)	1098.51 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.20 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	17054, 3828, 2982
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.112, 1.03
No. of reflections	3828
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o3159–o3160. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3390. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327–o3328. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Shahani, T., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3514. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Pages o1877-o1878

doi:10.1107/S1600536812023124

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2E)-3-(4-Cyano­phen­yl)-1-(4,4′′-di­fluoro-5′-meth­­oxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(2E)-3-(4-Cyanophenyl)-1-(4,4′′-difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one