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

Fun, H.-K.; Chia, T.S.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812013852

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1314-o1315

doi:10.1107/S1600536812013852

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

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^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 26 March 2012; accepted 30 March 2012; online 6 April 2012)

In the title compound, C₂₈H₁₉BrF₂O₂, the central benzene ring makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring and two terminal fluoro-substituted benzene rings, respectively. In the crystal, molecules are linked by C—H⋯F hydrogen bonds into infinite chains along [110]. Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.683 (2) Å] also occur and short intermolecular F⋯F contacts [2.833 (4) Å] are observed.

Related literature

For related structures and background to terphenyl chalcones, see: Fun et al. (2011a ,b , 2012 ). For reference bond lengths, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₈H₁₉BrF₂O₂
M_r = 505.34
Monoclinic, C 2/c
a = 22.4861 (6) Å
b = 6.9006 (2) Å
c = 28.6933 (8) Å
β = 101.286 (2)°
V = 4366.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.92 mm⁻¹
T = 100 K
0.37 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.533, T_max = 0.863
24190 measured reflections
6414 independent reflections
4483 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.134
S = 1.11
6414 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −1.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C1—C6 and C10—C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28A⋯F2ⁱ	0.96	2.51	3.448 (4)	166
C4—H4A⋯Cg1ⁱⁱ	0.93	2.99	3.712 (5)	136
C20—H20A⋯Cg2ⁱⁱⁱ	0.93	2.72	3.383 (4)	129
C27—H27A⋯Cg1^iv	0.93	2.95	3.735 (4)	143
C28—H28B⋯Cg2^v	0.96	2.82	3.485 (4)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x, -y-1, z-{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) -x-1, -y, -z; (v) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ .

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/S1600536812013852/hb6704sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013852/hb6704Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013852/hb6704Isup3.cml

checkCIF report

Comment top

In continuation of our work on the synthesis and structures of terphenyl chalcones (Fun et al., 2011a,b), the title compound (I) is now described. 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 (C10–C15) makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring (C1–C6) and two terminal fluoro-substituted benzene rings (C16–C21 & C22–C27), respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b, 2012).

In the crystal (Fig. 2), molecules are linked by C28—H28A···F2 hydrogen bonds into infinite chains along [110]. The crystal is further stabilized by C—H···π interactions (Table 1), involving Cg1 and Cg2 which are the centroids of C1—C6 and C10—C15 rings, respectively. π–π interaction is also observed with Cg4···Cg4 distance of 3.683 (2) Å [symmetry code: -1/2-X,3/2-Y,-Z], where Cg4 is the centroid of C22–C27 ring.

Related literature top

For related structures and background to terphenyl chalcones, see: Fun et al. (2011a,b, 2012). For reference bond lengths, see: Allen et al. (1987). 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 2-bromobenzaldehyde (0.185 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 needles were grown from DMF solution by slow evaporation method and yield of the compound was 79%. (m.p.: 440 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 with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

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

Crystal data top

C₂₈H₁₉BrF₂O₂	F(000) = 2048
M_r = 505.34	D_x = 1.538 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4738 reflections
a = 22.4861 (6) Å	θ = 2.6–29.4°
b = 6.9006 (2) Å	µ = 1.92 mm⁻¹
c = 28.6933 (8) Å	T = 100 K
β = 101.286 (2)°	Needle, colourless
V = 4366.2 (2) Å³	0.37 × 0.12 × 0.08 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	6414 independent reflections
Radiation source: fine-focus sealed tube	4483 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ϕ and ω scans	θ_max = 30.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −31→23
T_min = 0.533, T_max = 0.863	k = −9→9
24190 measured reflections	l = −40→39

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0321P)² + 25.8799P] where P = (F_o² + 2F_c²)/3
6414 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −1.09 e Å⁻³

Crystal data top

C₂₈H₁₉BrF₂O₂	V = 4366.2 (2) Å³
M_r = 505.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.4861 (6) Å	µ = 1.92 mm⁻¹
b = 6.9006 (2) Å	T = 100 K
c = 28.6933 (8) Å	0.37 × 0.12 × 0.08 mm
β = 101.286 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6414 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4483 reflections with I > 2σ(I)
T_min = 0.533, T_max = 0.863	R_int = 0.076
24190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0321P)² + 25.8799P] where P = (F_o² + 2F_c²)/3
6414 reflections	Δρ_max = 0.72 e Å⁻³
299 parameters	Δρ_min = −1.09 e Å⁻³

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	0.05500 (11)	1.3787 (4)	0.23294 (8)	0.0264 (6)
F2	−0.34855 (10)	0.4660 (3)	−0.01133 (9)	0.0242 (5)
Br1	0.327887 (17)	0.59947 (6)	0.161236 (15)	0.02040 (11)
O1	0.04875 (11)	0.3643 (4)	0.05277 (10)	0.0186 (6)
O2	0.11379 (12)	0.8145 (4)	0.10429 (10)	0.0227 (6)
C1	0.29189 (17)	0.3696 (6)	0.17939 (13)	0.0164 (8)
C2	0.32983 (18)	0.2283 (6)	0.20296 (13)	0.0205 (9)
H2A	0.3716	0.2470	0.2094	0.025*
C3	0.30549 (19)	0.0591 (6)	0.21700 (15)	0.0235 (9)
H3A	0.3308	−0.0355	0.2333	0.028*
C4	0.2435 (2)	0.0309 (6)	0.20675 (16)	0.0252 (10)
H4A	0.2271	−0.0833	0.2160	0.030*
C5	0.20594 (18)	0.1712 (6)	0.18288 (15)	0.0217 (9)
H5A	0.1644	0.1484	0.1755	0.026*
C6	0.22854 (17)	0.3485 (6)	0.16924 (14)	0.0175 (8)
C7	0.18826 (17)	0.5015 (6)	0.14592 (14)	0.0171 (8)
H7A	0.2064	0.6160	0.1389	0.020*
C8	0.12818 (16)	0.4921 (6)	0.13392 (14)	0.0162 (8)
H8A	0.1087	0.3784	0.1398	0.019*
C9	0.09102 (16)	0.6582 (6)	0.11128 (14)	0.0152 (8)
C10	0.02379 (15)	0.6264 (5)	0.09697 (13)	0.0134 (7)
C11	−0.01873 (16)	0.7463 (5)	0.11261 (13)	0.0132 (7)
C12	−0.08046 (16)	0.7099 (5)	0.09609 (13)	0.0131 (7)
H12A	−0.1089	0.7873	0.1068	0.016*
C13	−0.10049 (16)	0.5610 (5)	0.06407 (13)	0.0130 (7)
C14	−0.05778 (16)	0.4412 (5)	0.04891 (13)	0.0140 (8)
H14A	−0.0705	0.3409	0.0277	0.017*
C15	0.00371 (16)	0.4725 (6)	0.06567 (14)	0.0149 (8)
C16	−0.00013 (15)	0.9085 (6)	0.14622 (13)	0.0149 (7)
C17	0.04441 (17)	0.8892 (6)	0.18743 (14)	0.0195 (8)
H17A	0.0624	0.7691	0.1952	0.023*
C18	0.06198 (17)	1.0457 (6)	0.21673 (14)	0.0183 (8)
H18A	0.0915	1.0315	0.2442	0.022*
C19	0.03536 (17)	1.2232 (6)	0.20488 (14)	0.0168 (8)
C20	−0.01063 (17)	1.2479 (6)	0.16598 (14)	0.0170 (8)
H20A	−0.0298	1.3671	0.1596	0.020*
C21	−0.02756 (15)	1.0898 (6)	0.13661 (13)	0.0146 (7)
H21A	−0.0580	1.1046	0.1098	0.018*
C22	−0.16673 (16)	0.5323 (5)	0.04452 (13)	0.0129 (7)
C23	−0.18668 (17)	0.5112 (6)	−0.00430 (14)	0.0167 (8)
H23A	−0.1588	0.5115	−0.0243	0.020*
C24	−0.24795 (17)	0.4900 (5)	−0.02318 (14)	0.0172 (8)
H24A	−0.2616	0.4772	−0.0558	0.021*
C25	−0.28826 (17)	0.4882 (6)	0.00758 (15)	0.0176 (8)
C26	−0.27040 (17)	0.5068 (6)	0.05564 (15)	0.0182 (8)
H26A	−0.2986	0.5034	0.0754	0.022*
C27	−0.20866 (17)	0.5311 (5)	0.07448 (14)	0.0150 (8)
H27A	−0.1955	0.5466	0.1071	0.018*
C28	0.03253 (18)	0.1869 (6)	0.02761 (15)	0.0206 (9)
H28A	0.0686	0.1224	0.0226	0.031*
H28B	0.0068	0.2145	−0.0025	0.031*
H28C	0.0113	0.1049	0.0459	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0268 (13)	0.0204 (13)	0.0315 (14)	−0.0099 (11)	0.0043 (10)	−0.0100 (11)
F2	0.0090 (10)	0.0241 (13)	0.0374 (14)	0.0011 (9)	−0.0004 (10)	−0.0055 (11)
Br1	0.00986 (16)	0.0217 (2)	0.0293 (2)	−0.00161 (18)	0.00283 (13)	−0.00163 (19)
O1	0.0135 (12)	0.0155 (14)	0.0275 (15)	0.0042 (11)	0.0056 (11)	−0.0053 (11)
O2	0.0125 (13)	0.0180 (15)	0.0377 (18)	0.0013 (12)	0.0054 (12)	0.0066 (13)
C1	0.0171 (18)	0.017 (2)	0.0142 (18)	0.0018 (15)	0.0005 (14)	−0.0030 (15)
C2	0.0183 (19)	0.026 (2)	0.015 (2)	0.0079 (17)	−0.0029 (15)	−0.0044 (17)
C3	0.028 (2)	0.019 (2)	0.023 (2)	0.0101 (18)	0.0023 (17)	0.0017 (17)
C4	0.028 (2)	0.016 (2)	0.033 (3)	0.0005 (18)	0.0101 (19)	0.0042 (18)
C5	0.0141 (18)	0.019 (2)	0.033 (2)	0.0015 (16)	0.0076 (17)	0.0045 (18)
C6	0.0157 (18)	0.016 (2)	0.020 (2)	0.0028 (15)	0.0029 (15)	0.0022 (15)
C7	0.0131 (17)	0.018 (2)	0.021 (2)	0.0006 (16)	0.0046 (15)	0.0023 (16)
C8	0.0104 (17)	0.018 (2)	0.022 (2)	−0.0023 (15)	0.0057 (15)	0.0029 (16)
C9	0.0111 (17)	0.0147 (19)	0.022 (2)	0.0018 (14)	0.0080 (15)	0.0003 (15)
C10	0.0082 (15)	0.0132 (19)	0.0184 (19)	−0.0001 (14)	0.0017 (13)	0.0036 (15)
C11	0.0102 (16)	0.0144 (19)	0.0146 (18)	0.0022 (14)	0.0013 (14)	0.0022 (15)
C12	0.0115 (16)	0.0111 (18)	0.0176 (19)	0.0017 (15)	0.0051 (14)	0.0014 (14)
C13	0.0132 (16)	0.0105 (18)	0.0148 (18)	−0.0021 (14)	0.0015 (14)	0.0005 (14)
C14	0.0137 (17)	0.0102 (19)	0.0181 (19)	0.0008 (14)	0.0034 (14)	−0.0004 (14)
C15	0.0097 (16)	0.0136 (18)	0.022 (2)	0.0015 (14)	0.0060 (15)	0.0028 (15)
C16	0.0113 (16)	0.0156 (18)	0.0192 (19)	−0.0009 (16)	0.0064 (14)	0.0009 (16)
C17	0.0166 (18)	0.017 (2)	0.024 (2)	0.0006 (17)	0.0023 (15)	−0.0001 (17)
C18	0.0131 (17)	0.021 (2)	0.019 (2)	−0.0023 (16)	−0.0007 (15)	0.0005 (16)
C19	0.0161 (18)	0.0149 (19)	0.021 (2)	−0.0087 (16)	0.0068 (15)	−0.0065 (16)
C20	0.0149 (18)	0.0127 (19)	0.026 (2)	−0.0039 (15)	0.0109 (16)	0.0009 (16)
C21	0.0098 (15)	0.0173 (19)	0.0176 (18)	0.0006 (16)	0.0044 (13)	0.0006 (16)
C22	0.0104 (16)	0.0082 (17)	0.020 (2)	−0.0028 (14)	0.0026 (14)	−0.0002 (14)
C23	0.0154 (18)	0.0137 (19)	0.021 (2)	0.0025 (15)	0.0041 (15)	−0.0013 (16)
C24	0.0182 (19)	0.0120 (19)	0.019 (2)	0.0019 (16)	−0.0017 (16)	−0.0011 (15)
C25	0.0112 (17)	0.0096 (18)	0.030 (2)	0.0011 (15)	−0.0007 (16)	−0.0008 (16)
C26	0.0128 (18)	0.016 (2)	0.027 (2)	−0.0007 (16)	0.0084 (16)	−0.0004 (17)
C27	0.0150 (18)	0.0113 (18)	0.018 (2)	0.0007 (15)	0.0027 (15)	−0.0013 (15)
C28	0.0177 (19)	0.017 (2)	0.028 (2)	0.0032 (16)	0.0070 (17)	−0.0049 (17)

Geometric parameters (Å, º) top

F1—C19	1.362 (4)	C13—C14	1.400 (5)
F2—C25	1.366 (4)	C13—C22	1.499 (5)
Br1—C1	1.899 (4)	C14—C15	1.389 (5)
O1—C15	1.366 (4)	C14—H14A	0.9300
O1—C28	1.432 (5)	C16—C21	1.398 (5)
O2—C9	1.227 (5)	C16—C17	1.398 (5)
C1—C2	1.382 (5)	C17—C18	1.378 (6)
C1—C6	1.405 (5)	C17—H17A	0.9300
C2—C3	1.383 (6)	C18—C19	1.377 (6)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.380 (6)	C19—C20	1.375 (5)
C3—H3A	0.9300	C20—C21	1.386 (5)
C4—C5	1.377 (6)	C20—H20A	0.9300
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.409 (6)	C22—C23	1.392 (5)
C5—H5A	0.9300	C22—C27	1.395 (5)
C6—C7	1.465 (5)	C23—C24	1.386 (5)
C7—C8	1.329 (5)	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.384 (6)
C8—C9	1.490 (5)	C24—H24A	0.9300
C8—H8A	0.9300	C25—C26	1.365 (6)
C9—C10	1.503 (5)	C26—C27	1.398 (5)
C10—C11	1.403 (5)	C26—H26A	0.9300
C10—C15	1.407 (5)	C27—H27A	0.9300
C11—C12	1.399 (5)	C28—H28A	0.9600
C11—C16	1.483 (5)	C28—H28B	0.9600
C12—C13	1.393 (5)	C28—H28C	0.9600
C12—H12A	0.9300

C15—O1—C28	118.3 (3)	O1—C15—C10	115.0 (3)
C2—C1—C6	122.1 (4)	C14—C15—C10	120.8 (3)
C2—C1—Br1	117.9 (3)	C21—C16—C17	117.9 (4)
C6—C1—Br1	120.0 (3)	C21—C16—C11	119.3 (3)
C1—C2—C3	119.8 (4)	C17—C16—C11	122.8 (4)
C1—C2—H2A	120.1	C18—C17—C16	120.9 (4)
C3—C2—H2A	120.1	C18—C17—H17A	119.6
C4—C3—C2	119.8 (4)	C16—C17—H17A	119.6
C4—C3—H3A	120.1	C19—C18—C17	119.2 (4)
C2—C3—H3A	120.1	C19—C18—H18A	120.4
C5—C4—C3	120.2 (4)	C17—C18—H18A	120.4
C5—C4—H4A	119.9	F1—C19—C20	119.2 (4)
C3—C4—H4A	119.9	F1—C19—C18	118.7 (3)
C4—C5—C6	122.0 (4)	C20—C19—C18	122.1 (4)
C4—C5—H5A	119.0	C19—C20—C21	118.0 (4)
C6—C5—H5A	119.0	C19—C20—H20A	121.0
C1—C6—C5	116.0 (3)	C21—C20—H20A	121.0
C1—C6—C7	122.1 (4)	C20—C21—C16	121.8 (3)
C5—C6—C7	121.9 (3)	C20—C21—H21A	119.1
C8—C7—C6	126.1 (4)	C16—C21—H21A	119.1
C8—C7—H7A	116.9	C23—C22—C27	119.7 (3)
C6—C7—H7A	116.9	C23—C22—C13	119.4 (3)
C7—C8—C9	122.0 (4)	C27—C22—C13	120.8 (3)
C7—C8—H8A	119.0	C24—C23—C22	120.3 (4)
C9—C8—H8A	119.0	C24—C23—H23A	119.9
O2—C9—C8	122.1 (3)	C22—C23—H23A	119.9
O2—C9—C10	120.9 (3)	C25—C24—C23	118.5 (4)
C8—C9—C10	117.0 (3)	C25—C24—H24A	120.8
C11—C10—C15	119.7 (3)	C23—C24—H24A	120.8
C11—C10—C9	122.6 (3)	C26—C25—F2	119.0 (3)
C15—C10—C9	117.7 (3)	C26—C25—C24	122.9 (4)
C12—C11—C10	118.6 (3)	F2—C25—C24	118.1 (3)
C12—C11—C16	119.4 (3)	C25—C26—C27	118.4 (4)
C10—C11—C16	122.0 (3)	C25—C26—H26A	120.8
C13—C12—C11	121.8 (3)	C27—C26—H26A	120.8
C13—C12—H12A	119.1	C22—C27—C26	120.1 (4)
C11—C12—H12A	119.1	C22—C27—H27A	119.9
C12—C13—C14	119.2 (3)	C26—C27—H27A	119.9
C12—C13—C22	120.9 (3)	O1—C28—H28A	109.5
C14—C13—C22	119.8 (3)	O1—C28—H28B	109.5
C15—C14—C13	119.9 (3)	H28A—C28—H28B	109.5
C15—C14—H14A	120.1	O1—C28—H28C	109.5
C13—C14—H14A	120.1	H28A—C28—H28C	109.5
O1—C15—C14	124.2 (3)	H28B—C28—H28C	109.5

C6—C1—C2—C3	0.4 (6)	C13—C14—C15—C10	−1.5 (6)
Br1—C1—C2—C3	179.7 (3)	C11—C10—C15—O1	−179.8 (3)
C1—C2—C3—C4	1.0 (6)	C9—C10—C15—O1	1.8 (5)
C2—C3—C4—C5	−0.4 (6)	C11—C10—C15—C14	1.9 (6)
C3—C4—C5—C6	−1.7 (7)	C9—C10—C15—C14	−176.4 (3)
C2—C1—C6—C5	−2.4 (6)	C12—C11—C16—C21	−47.1 (5)
Br1—C1—C6—C5	178.4 (3)	C10—C11—C16—C21	133.3 (4)
C2—C1—C6—C7	177.6 (4)	C12—C11—C16—C17	133.3 (4)
Br1—C1—C6—C7	−1.7 (5)	C10—C11—C16—C17	−46.2 (5)
C4—C5—C6—C1	3.0 (6)	C21—C16—C17—C18	−2.1 (6)
C4—C5—C6—C7	−176.9 (4)	C11—C16—C17—C18	177.5 (4)
C1—C6—C7—C8	178.2 (4)	C16—C17—C18—C19	−0.4 (6)
C5—C6—C7—C8	−1.9 (7)	C17—C18—C19—F1	−177.1 (3)
C6—C7—C8—C9	178.5 (4)	C17—C18—C19—C20	3.5 (6)
C7—C8—C9—O2	−2.9 (6)	F1—C19—C20—C21	176.6 (3)
C7—C8—C9—C10	176.8 (4)	C18—C19—C20—C21	−4.0 (6)
O2—C9—C10—C11	−55.4 (5)	C19—C20—C21—C16	1.3 (5)
C8—C9—C10—C11	124.8 (4)	C17—C16—C21—C20	1.6 (5)
O2—C9—C10—C15	122.9 (4)	C11—C16—C21—C20	−178.0 (3)
C8—C9—C10—C15	−56.9 (5)	C12—C13—C22—C23	130.6 (4)
C15—C10—C11—C12	−0.6 (5)	C14—C13—C22—C23	−47.2 (5)
C9—C10—C11—C12	177.7 (3)	C12—C13—C22—C27	−47.8 (5)
C15—C10—C11—C16	179.0 (3)	C14—C13—C22—C27	134.4 (4)
C9—C10—C11—C16	−2.7 (6)	C27—C22—C23—C24	0.2 (6)
C10—C11—C12—C13	−1.2 (5)	C13—C22—C23—C24	−178.2 (3)
C16—C11—C12—C13	179.2 (3)	C22—C23—C24—C25	−0.7 (6)
C11—C12—C13—C14	1.7 (5)	C23—C24—C25—C26	0.1 (6)
C11—C12—C13—C22	−176.2 (3)	C23—C24—C25—F2	−179.6 (3)
C12—C13—C14—C15	−0.3 (5)	F2—C25—C26—C27	−179.4 (3)
C22—C13—C14—C15	177.6 (3)	C24—C25—C26—C27	0.8 (6)
C28—O1—C15—C14	−12.1 (5)	C23—C22—C27—C26	0.7 (6)
C28—O1—C15—C10	169.7 (3)	C13—C22—C27—C26	179.1 (3)
C13—C14—C15—O1	−179.6 (3)	C25—C26—C27—C22	−1.2 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C1—C6 and C10—C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···F2ⁱ	0.96	2.51	3.448 (4)	166
C4—H4A···Cg1ⁱⁱ	0.93	2.99	3.712 (5)	136
C20—H20A···Cg2ⁱⁱⁱ	0.93	2.72	3.383 (4)	129
C27—H27A···Cg1^iv	0.93	2.95	3.735 (4)	143
C28—H28B···Cg2^v	0.96	2.82	3.485 (4)	128

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y−1, z−1/2; (iii) x, y+1, z; (iv) −x−1, −y, −z; (v) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₂₈H₁₉BrF₂O₂
M_r	505.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	22.4861 (6), 6.9006 (2), 28.6933 (8)
β (°)	101.286 (2)
V (Å³)	4366.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.92
Crystal size (mm)	0.37 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.533, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	24190, 6414, 4483
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.709

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.134, 1.11
No. of reflections	6414
No. of parameters	299
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0321P)² + 25.8799P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.72, −1.09

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of C1—C6 and C10—C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···F2ⁱ	0.96	2.51	3.448 (4)	166
C4—H4A···Cg1ⁱⁱ	0.93	2.99	3.712 (5)	136
C20—H20A···Cg2ⁱⁱⁱ	0.93	2.72	3.383 (4)	129
C27—H27A···Cg1^iv	0.93	2.95	3.735 (4)	143
C28—H28B···Cg2^v	0.96	2.82	3.485 (4)	128

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y−1, z−1/2; (iii) x, y+1, z; (iv) −x−1, −y, −z; (v) x+1/2, y+3/2, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. 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

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. 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., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011b). 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. (2011a). 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 5| May 2012| Pages o1314-o1315

doi:10.1107/S1600536812013852

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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