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

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

doi:10.1107/S1600536811050884

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3514

https://doi.org/10.1107/S1600536811050884

Open

access

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

Hoong-Kun Fun,^a ^*‡ Tara Shahani,^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 25 November 2011; accepted 26 November 2011; online 30 November 2011)

In the title compound, C₂₉H₂₁BrF₂O₃, the dihedral angles between the central anisole ring and the pendant fluorobenzene rings are 48.86 (19) and 31.89 (18)°. The dihedral angle between the anisole ring and the 1-bromo-2-methoxybenzene ring linked via the enone bridge is 82.95 (17)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into C(11) chains propagating along [010].

Related literature

For related structures and background to chalcones and their properties, see: Fun et al. (2010a ,b ).

Experimental

Crystal data

C₂₉H₂₁BrF₂O₃
M_r = 535.37
Monoclinic, P 2₁ /n
a = 9.6902 (6) Å
b = 20.3345 (12) Å
c = 12.9556 (8) Å
β = 110.636 (1)°
V = 2389.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.77 mm⁻¹
T = 296 K
0.42 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.525, T_max = 0.843
22747 measured reflections
5455 independent reflections
4111 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.183
S = 1.04
5455 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 1.96 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29B⋯O2ⁱ	0.96	2.41	3.303 (6)	155
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811050884/hb6536sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050884/hb6536Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050884/hb6536Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of substituted chalcone derivatives, (Fun et al., 2010a,b), the title compound (I) was prepared and its crystal structure is reported. The precursor of the title compound was prepared from 4,4'-difluoro chalcone by several steps.

The title molecule is built up (Fig. 1) from four units, namely: two fluorobenzenes (C1–C6/F1) and (C13–C18/F2), a anisole (C7–C12/O1/C28) and a 1-bromo-2- methoxybenzene (C22/C27/Br1/C29/O3). The anisole moiety makes dihedral angles of 48.86 (19)°, 31.89 (18)° and 82.95 (17)° with the two fluorobenzenes and 1-bromo-2-methoxybenzene moieties respectively.

In the crystal (Fig. 2), C29—H29B···O2 hydrogen bonds link the molecules into chains along [010].

Related literature top

For related structures and background to chalcones and their properties, see: Fun et al. (2010a,b).

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 3-bromo-4-methoxybenzaldehyde (0.215 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 blocks of (I) were grown from DMF by slow evaporation and the yield of the compound was 82%. Mp: 452 K.

Structure description top

In the crystal (Fig. 2), C29—H29B···O2 hydrogen bonds link the molecules into chains along [010].

For related structures and background to chalcones and their properties, see: Fun et al. (2010a,b).

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 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, showing chains along [010].

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

Crystal data top

C₂₉H₂₁BrF₂O₃	F(000) = 1088
M_r = 535.37	D_x = 1.488 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5893 reflections
a = 9.6902 (6) Å	θ = 2.3–26.7°
b = 20.3345 (12) Å	µ = 1.77 mm⁻¹
c = 12.9556 (8) Å	T = 296 K
β = 110.636 (1)°	Block, colourless
V = 2389.0 (3) Å³	0.42 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	5455 independent reflections
Radiation source: fine-focus sealed tube	4111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.525, T_max = 0.843	k = −26→26
22747 measured reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1002P)² + 2.471P] where P = (F_o² + 2F_c²)/3
5455 reflections	(Δ/σ)_max < 0.001
318 parameters	Δρ_max = 1.96 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₉H₂₁BrF₂O₃	V = 2389.0 (3) Å³
M_r = 535.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6902 (6) Å	µ = 1.77 mm⁻¹
b = 20.3345 (12) Å	T = 296 K
c = 12.9556 (8) Å	0.42 × 0.15 × 0.10 mm
β = 110.636 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5455 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4111 reflections with I > 2σ(I)
T_min = 0.525, T_max = 0.843	R_int = 0.032
22747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	Δρ_max = 1.96 e Å⁻³
5455 reflections	Δρ_min = −0.39 e Å⁻³
318 parameters

Special details top

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
Br1	0.78171 (4)	0.01704 (2)	0.94057 (4)	0.05838 (18)
F1	−0.8898 (3)	0.02285 (16)	0.3378 (3)	0.0829 (9)
F2	−0.0561 (4)	0.2180 (2)	1.2026 (2)	0.0959 (11)
O1	0.0167 (3)	0.16491 (14)	0.5498 (2)	0.0466 (6)
O2	0.1325 (3)	0.24970 (13)	0.7986 (2)	0.0544 (7)
O3	0.6494 (3)	−0.11520 (13)	0.9196 (2)	0.0549 (7)
C1	−0.5661 (4)	0.0674 (2)	0.5680 (3)	0.0491 (9)
H1A	−0.5261	0.0601	0.6436	0.059*
C2	−0.7014 (5)	0.0404 (2)	0.5087 (4)	0.0576 (10)
H2A	−0.7535	0.0160	0.5435	0.069*
C3	−0.7566 (4)	0.0505 (2)	0.3978 (4)	0.0556 (10)
C4	−0.6843 (5)	0.0873 (2)	0.3442 (3)	0.0593 (11)
H4A	−0.7248	0.0932	0.2683	0.071*
C5	−0.5502 (4)	0.1154 (2)	0.4048 (3)	0.0501 (9)
H5A	−0.5012	0.1413	0.3695	0.060*
C6	−0.4877 (4)	0.10529 (17)	0.5181 (3)	0.0377 (7)
C7	−0.3388 (4)	0.13085 (16)	0.5830 (3)	0.0359 (7)
C8	−0.2327 (4)	0.13664 (16)	0.5331 (3)	0.0374 (7)
H8A	−0.2575	0.1274	0.4585	0.045*
C9	−0.0913 (4)	0.15609 (16)	0.5949 (3)	0.0352 (7)
C10	−0.0501 (4)	0.17015 (14)	0.7068 (3)	0.0334 (6)
C11	−0.1565 (4)	0.16733 (15)	0.7562 (3)	0.0343 (7)
C12	−0.2992 (4)	0.14751 (16)	0.6934 (3)	0.0370 (7)
H12A	−0.3700	0.1454	0.7265	0.044*
C13	−0.1240 (4)	0.18309 (16)	0.8754 (3)	0.0358 (7)
C14	−0.0050 (4)	0.1557 (2)	0.9580 (3)	0.0498 (9)
H14A	0.0608	0.1290	0.9396	0.060*
C15	0.0168 (5)	0.1677 (3)	1.0683 (3)	0.0655 (13)
H15A	0.0965	0.1490	1.1238	0.079*
C16	−0.0789 (5)	0.2065 (3)	1.0936 (3)	0.0594 (11)
C17	−0.1966 (5)	0.2347 (2)	1.0165 (3)	0.0594 (11)
H17A	−0.2609	0.2615	1.0366	0.071*
C18	−0.2189 (4)	0.2226 (2)	0.9060 (3)	0.0501 (9)
H18A	−0.2995	0.2414	0.8517	0.060*
C19	0.1073 (4)	0.19288 (17)	0.7681 (3)	0.0387 (7)
C20	0.2285 (4)	0.14534 (19)	0.7912 (3)	0.0448 (8)
H20A	0.3242	0.1617	0.8134	0.054*
C21	0.2106 (4)	0.08060 (18)	0.7826 (3)	0.0417 (8)
H21A	0.1137	0.0658	0.7531	0.050*
C22	0.3256 (4)	0.02905 (18)	0.8141 (3)	0.0409 (8)
C23	0.2855 (5)	−0.03641 (19)	0.8042 (3)	0.0484 (9)
H23A	0.1861	−0.0475	0.7752	0.058*
C24	0.3908 (4)	−0.08650 (18)	0.8367 (3)	0.0489 (9)
H24A	0.3613	−0.1303	0.8284	0.059*
C25	0.5372 (4)	−0.07106 (17)	0.8808 (3)	0.0421 (8)
C26	0.5802 (4)	−0.00506 (17)	0.8881 (3)	0.0383 (7)
C27	0.4753 (4)	0.04443 (16)	0.8566 (3)	0.0400 (7)
H27A	0.5050	0.0882	0.8638	0.048*
C28	−0.0242 (5)	0.1550 (3)	0.4338 (3)	0.0589 (11)
H28A	0.0605	0.1613	0.4128	0.088*
H28B	−0.0993	0.1861	0.3953	0.088*
H28C	−0.0611	0.1112	0.4154	0.088*
C29	0.6106 (6)	−0.1824 (2)	0.9226 (5)	0.0765 (16)
H29A	0.6980	−0.2078	0.9582	0.115*
H29B	0.5628	−0.1982	0.8487	0.115*
H29D	0.5447	−0.1866	0.9629	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0392 (3)	0.0565 (3)	0.0762 (3)	−0.00361 (17)	0.0164 (2)	0.00561 (19)
F1	0.0413 (15)	0.103 (2)	0.084 (2)	−0.0160 (14)	−0.0029 (13)	−0.0303 (17)
F2	0.085 (2)	0.171 (3)	0.0257 (12)	0.012 (2)	0.0129 (12)	−0.0121 (16)
O1	0.0403 (14)	0.0676 (16)	0.0333 (12)	−0.0086 (12)	0.0147 (10)	−0.0034 (11)
O2	0.0516 (16)	0.0418 (13)	0.0579 (17)	−0.0058 (12)	0.0043 (13)	−0.0058 (12)
O3	0.0495 (16)	0.0413 (13)	0.0627 (18)	0.0056 (12)	0.0056 (13)	0.0002 (12)
C1	0.045 (2)	0.062 (2)	0.0364 (18)	−0.0089 (17)	0.0105 (16)	−0.0036 (17)
C2	0.047 (2)	0.069 (2)	0.056 (2)	−0.014 (2)	0.0173 (19)	−0.010 (2)
C3	0.0277 (18)	0.067 (3)	0.061 (3)	−0.0006 (17)	0.0009 (17)	−0.019 (2)
C4	0.042 (2)	0.084 (3)	0.038 (2)	0.007 (2)	−0.0024 (17)	−0.0061 (19)
C5	0.040 (2)	0.072 (2)	0.0331 (18)	0.0042 (18)	0.0068 (15)	0.0042 (17)
C6	0.0321 (17)	0.0477 (17)	0.0295 (16)	0.0008 (14)	0.0061 (13)	−0.0046 (14)
C7	0.0331 (17)	0.0390 (15)	0.0311 (16)	0.0017 (13)	0.0059 (13)	0.0005 (12)
C8	0.0419 (19)	0.0414 (16)	0.0268 (15)	−0.0006 (14)	0.0095 (13)	−0.0013 (13)
C9	0.0356 (17)	0.0369 (15)	0.0333 (16)	0.0004 (13)	0.0124 (13)	0.0005 (12)
C10	0.0341 (17)	0.0321 (14)	0.0296 (15)	0.0013 (12)	0.0055 (13)	0.0027 (12)
C11	0.0377 (18)	0.0340 (14)	0.0264 (15)	0.0012 (13)	0.0056 (13)	0.0014 (12)
C12	0.0354 (17)	0.0430 (16)	0.0308 (16)	0.0004 (13)	0.0094 (13)	0.0000 (13)
C13	0.0360 (17)	0.0425 (16)	0.0256 (15)	−0.0026 (13)	0.0068 (13)	0.0007 (12)
C14	0.040 (2)	0.069 (2)	0.0356 (18)	0.0120 (18)	0.0085 (15)	0.0064 (17)
C15	0.048 (2)	0.107 (4)	0.031 (2)	0.016 (2)	0.0018 (17)	0.011 (2)
C16	0.056 (2)	0.095 (3)	0.0243 (17)	−0.003 (2)	0.0115 (16)	−0.0065 (19)
C17	0.057 (3)	0.081 (3)	0.040 (2)	0.014 (2)	0.0156 (18)	−0.0076 (19)
C18	0.050 (2)	0.061 (2)	0.0320 (18)	0.0145 (18)	0.0047 (15)	−0.0016 (16)
C19	0.0379 (18)	0.0423 (17)	0.0318 (16)	−0.0030 (14)	0.0070 (13)	0.0006 (13)
C20	0.0299 (17)	0.055 (2)	0.044 (2)	0.0015 (15)	0.0064 (15)	0.0005 (16)
C21	0.0341 (18)	0.0487 (18)	0.0388 (18)	0.0025 (14)	0.0085 (14)	0.0002 (15)
C22	0.0376 (19)	0.0495 (18)	0.0340 (17)	0.0020 (15)	0.0103 (14)	0.0016 (14)
C23	0.041 (2)	0.0477 (18)	0.048 (2)	0.0005 (16)	0.0061 (16)	−0.0040 (16)
C24	0.048 (2)	0.0403 (17)	0.051 (2)	−0.0066 (16)	0.0073 (17)	−0.0069 (16)
C25	0.045 (2)	0.0394 (17)	0.0386 (18)	0.0044 (14)	0.0112 (15)	−0.0018 (14)
C26	0.0398 (18)	0.0420 (16)	0.0336 (17)	−0.0008 (14)	0.0137 (14)	0.0026 (13)
C27	0.046 (2)	0.0360 (15)	0.0387 (18)	0.0007 (14)	0.0164 (15)	0.0025 (13)
C28	0.054 (2)	0.089 (3)	0.038 (2)	−0.007 (2)	0.0220 (18)	−0.008 (2)
C29	0.070 (3)	0.039 (2)	0.089 (4)	0.002 (2)	−0.011 (3)	0.001 (2)

Geometric parameters (Å, º) top

Br1—C26	1.882 (4)	C13—C14	1.384 (5)
F1—C3	1.370 (5)	C14—C15	1.390 (6)
F2—C16	1.370 (4)	C14—H14A	0.9300
O1—C9	1.378 (4)	C15—C16	1.344 (6)
O1—C28	1.427 (5)	C15—H15A	0.9300
O2—C19	1.218 (4)	C16—C17	1.351 (6)
O3—C25	1.362 (4)	C17—C18	1.392 (5)
O3—C29	1.422 (5)	C17—H17A	0.9300
C1—C2	1.379 (6)	C18—H18A	0.9300
C1—C6	1.390 (5)	C19—C20	1.468 (5)
C1—H1A	0.9300	C20—C21	1.327 (5)
C2—C3	1.360 (6)	C20—H20A	0.9300
C2—H2A	0.9300	C21—C22	1.479 (5)
C3—C4	1.369 (7)	C21—H21A	0.9300
C4—C5	1.383 (6)	C22—C23	1.380 (5)
C4—H4A	0.9300	C22—C27	1.394 (5)
C5—C6	1.392 (5)	C23—C24	1.398 (5)
C5—H5A	0.9300	C23—H23A	0.9300
C6—C7	1.485 (5)	C24—C25	1.366 (5)
C7—C12	1.386 (5)	C24—H24A	0.9300
C7—C8	1.398 (5)	C25—C26	1.398 (5)
C8—C9	1.379 (5)	C26—C27	1.386 (5)
C8—H8A	0.9300	C27—H27A	0.9300
C9—C10	1.391 (4)	C28—H28A	0.9600
C10—C11	1.394 (5)	C28—H28B	0.9600
C10—C19	1.522 (5)	C28—H28C	0.9600
C11—C12	1.394 (5)	C29—H29A	0.9600
C11—C13	1.498 (4)	C29—H29B	0.9600
C12—H12A	0.9300	C29—H29D	0.9600
C13—C18	1.380 (5)

C9—O1—C28	117.3 (3)	C15—C16—F2	118.5 (4)
C25—O3—C29	117.3 (3)	C17—C16—F2	118.5 (4)
C2—C1—C6	122.0 (4)	C16—C17—C18	118.0 (4)
C2—C1—H1A	119.0	C16—C17—H17A	121.0
C6—C1—H1A	119.0	C18—C17—H17A	121.0
C3—C2—C1	118.1 (4)	C13—C18—C17	121.4 (4)
C3—C2—H2A	120.9	C13—C18—H18A	119.3
C1—C2—H2A	120.9	C17—C18—H18A	119.3
C2—C3—C4	122.5 (4)	O2—C19—C20	120.3 (3)
C2—C3—F1	118.5 (4)	O2—C19—C10	120.5 (3)
C4—C3—F1	119.0 (4)	C20—C19—C10	119.3 (3)
C3—C4—C5	119.0 (4)	C21—C20—C19	124.3 (3)
C3—C4—H4A	120.5	C21—C20—H20A	117.8
C5—C4—H4A	120.5	C19—C20—H20A	117.8
C4—C5—C6	120.7 (4)	C20—C21—C22	128.0 (4)
C4—C5—H5A	119.7	C20—C21—H21A	116.0
C6—C5—H5A	119.7	C22—C21—H21A	116.0
C1—C6—C5	117.8 (3)	C23—C22—C27	118.2 (3)
C1—C6—C7	120.8 (3)	C23—C22—C21	119.9 (3)
C5—C6—C7	121.3 (3)	C27—C22—C21	121.9 (3)
C12—C7—C8	118.4 (3)	C22—C23—C24	121.6 (4)
C12—C7—C6	122.0 (3)	C22—C23—H23A	119.2
C8—C7—C6	119.6 (3)	C24—C23—H23A	119.2
C9—C8—C7	119.9 (3)	C25—C24—C23	119.9 (3)
C9—C8—H8A	120.1	C25—C24—H24A	120.0
C7—C8—H8A	120.1	C23—C24—H24A	120.0
O1—C9—C8	122.6 (3)	O3—C25—C24	125.4 (3)
O1—C9—C10	115.6 (3)	O3—C25—C26	115.3 (3)
C8—C9—C10	121.7 (3)	C24—C25—C26	119.3 (3)
C9—C10—C11	118.9 (3)	C27—C26—C25	120.5 (3)
C9—C10—C19	118.2 (3)	C27—C26—Br1	119.5 (3)
C11—C10—C19	122.7 (3)	C25—C26—Br1	120.0 (3)
C10—C11—C12	119.1 (3)	C26—C27—C22	120.4 (3)
C10—C11—C13	122.9 (3)	C26—C27—H27A	119.8
C12—C11—C13	118.0 (3)	C22—C27—H27A	119.8
C7—C12—C11	122.0 (3)	O1—C28—H28A	109.5
C7—C12—H12A	119.0	O1—C28—H28B	109.5
C11—C12—H12A	119.0	H28A—C28—H28B	109.5
C18—C13—C14	118.0 (3)	O1—C28—H28C	109.5
C18—C13—C11	120.1 (3)	H28A—C28—H28C	109.5
C14—C13—C11	121.8 (3)	H28B—C28—H28C	109.5
C13—C14—C15	120.5 (4)	O3—C29—H29A	109.5
C13—C14—H14A	119.8	O3—C29—H29B	109.5
C15—C14—H14A	119.8	H29A—C29—H29B	109.5
C16—C15—C14	119.1 (4)	O3—C29—H29D	109.5
C16—C15—H15A	120.5	H29A—C29—H29D	109.5
C14—C15—H15A	120.5	H29B—C29—H29D	109.5
C15—C16—C17	123.0 (4)

C6—C1—C2—C3	1.4 (7)	C12—C11—C13—C14	129.0 (4)
C1—C2—C3—C4	−1.4 (7)	C18—C13—C14—C15	0.2 (6)
C1—C2—C3—F1	178.8 (4)	C11—C13—C14—C15	−175.6 (4)
C2—C3—C4—C5	−0.1 (7)	C13—C14—C15—C16	−0.3 (7)
F1—C3—C4—C5	179.7 (4)	C14—C15—C16—C17	0.1 (8)
C3—C4—C5—C6	1.5 (6)	C14—C15—C16—F2	−179.9 (5)
C2—C1—C6—C5	−0.1 (6)	C15—C16—C17—C18	0.1 (8)
C2—C1—C6—C7	−176.8 (4)	F2—C16—C17—C18	−179.8 (5)
C4—C5—C6—C1	−1.4 (6)	C14—C13—C18—C17	0.0 (6)
C4—C5—C6—C7	175.3 (4)	C11—C13—C18—C17	175.9 (4)
C1—C6—C7—C12	−32.0 (5)	C16—C17—C18—C13	−0.2 (7)
C5—C6—C7—C12	151.4 (4)	C9—C10—C19—O2	108.8 (4)
C1—C6—C7—C8	146.0 (4)	C11—C10—C19—O2	−66.6 (4)
C5—C6—C7—C8	−30.6 (5)	C9—C10—C19—C20	−71.9 (4)
C12—C7—C8—C9	2.5 (5)	C11—C10—C19—C20	112.7 (4)
C6—C7—C8—C9	−175.6 (3)	O2—C19—C20—C21	165.2 (4)
C28—O1—C9—C8	1.9 (5)	C10—C19—C20—C21	−14.2 (5)
C28—O1—C9—C10	−176.1 (3)	C19—C20—C21—C22	−173.6 (3)
C7—C8—C9—O1	−177.7 (3)	C20—C21—C22—C23	176.7 (4)
C7—C8—C9—C10	0.2 (5)	C20—C21—C22—C27	−1.7 (6)
O1—C9—C10—C11	175.0 (3)	C27—C22—C23—C24	0.7 (6)
C8—C9—C10—C11	−3.0 (5)	C21—C22—C23—C24	−177.8 (4)
O1—C9—C10—C19	−0.5 (4)	C22—C23—C24—C25	0.9 (6)
C8—C9—C10—C19	−178.5 (3)	C29—O3—C25—C24	−5.3 (6)
C9—C10—C11—C12	3.0 (4)	C29—O3—C25—C26	174.8 (4)
C19—C10—C11—C12	178.4 (3)	C23—C24—C25—O3	177.1 (4)
C9—C10—C11—C13	−178.6 (3)	C23—C24—C25—C26	−3.0 (6)
C19—C10—C11—C13	−3.2 (5)	O3—C25—C26—C27	−176.6 (3)
C8—C7—C12—C11	−2.4 (5)	C24—C25—C26—C27	3.5 (5)
C6—C7—C12—C11	175.6 (3)	O3—C25—C26—Br1	3.6 (4)
C10—C11—C12—C7	−0.4 (5)	C24—C25—C26—Br1	−176.3 (3)
C13—C11—C12—C7	−178.9 (3)	C25—C26—C27—C22	−1.9 (5)
C10—C11—C13—C18	134.8 (4)	Br1—C26—C27—C22	177.9 (3)
C12—C11—C13—C18	−46.8 (5)	C23—C22—C27—C26	−0.2 (5)
C10—C11—C13—C14	−49.4 (5)	C21—C22—C27—C26	178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29B···O2ⁱ	0.96	2.41	3.303 (6)	155

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₁BrF₂O₃
M_r	535.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.6902 (6), 20.3345 (12), 12.9556 (8)
β (°)	110.636 (1)
V (Å³)	2389.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.77
Crystal size (mm)	0.42 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.525, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	22747, 5455, 4111
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.183, 1.04
No. of reflections	5455
No. of parameters	318
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.96, −0.39

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29B···O2ⁱ	0.96	2.41	3.303 (6)	155

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks 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 research facilities.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA. Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o582–o583. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o864–o865. Web of Science CSD CrossRef CAS 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3514

https://doi.org/10.1107/S1600536811050884

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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