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

Samshuddin, S.; Narayana, B.; Yathirajan, H.S.; Betz, R.; Gerber, T.; Hosten, E.

doi:10.1107/S1600536812017692

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1538-o1539

doi:10.1107/S1600536812017692

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

S. Samshuddin,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Richard Betz,^c ^* Thomas Gerber ^c and Eric Hosten ^c

^aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, ^bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 11 April 2012; accepted 20 April 2012; online 28 April 2012)

The title compound, C₂₈H₁₉ClF₂O₂, is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C—H⋯Cl and C—H⋯O contacts connect the molecules into layers lying perpendicular to the a axis. The shortest intercentroid distance between symmetry-related 4-fluorophenyl groups is 3.7547 (16) Å.

Related literature

For pharmacological background information about terphenyls, see: Astrue (2002 ); Liu (2006 ). For the crystal structures of other terphenyl derivatives, see: Betz et al. (2011a ,b ,c ,d ,e ); Samshuddin et al. (2011 ). For graph-set analysis, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₁₉ClF₂O₂
M_r = 460.88
Monoclinic, P 2₁ /c
a = 14.2065 (7) Å
b = 6.8651 (3) Å
c = 22.4817 (11) Å
β = 101.406 (2)°
V = 2149.32 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 200 K
0.40 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.918, T_max = 0.962
17828 measured reflections
5318 independent reflections
3817 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.141
S = 1.07
5318 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯Cl1ⁱ	0.95	2.73	3.641 (2)	161
C33—H33⋯Cl1ⁱⁱ	0.95	2.76	3.697 (3)	170
C43—H43⋯O1ⁱ	0.95	2.54	3.411 (3)	153
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017692/su2410sup1.cif

Supporting information file. DOI: 10.1107/S1600536812017692/su2410Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017692/su2410Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812017692/su2410Isup4.cml

checkCIF report

Comment top

Polysubstituted aromatics are key structures of great efficacy in synthetic, medicinal and natural product chemistry. Terphenyl derivatives exhibit a considerable range of biological activities and show anticoagulant, immunosuppressant, antithrombotic, neuroprotective, specific 5-lipoxygenase inhibitory and cytotoxic activity effects (Liu, 2006). Due to their promising biological activities terphenyls have received increasing research interest. Therefore, synthesis of polysubstituted aromatics has been a fascinating area in the field of organic chemistry (Astrue, 2002). The molecular and crystal structures of several terphenyl derivatives (Samshuddin et al., 2011; Betz et al., 2011a,b,c,d,e) have already been reported. In view of the importance of these derivatives, the title compound was prepared and its molecular and crystal structure is reported.

The C═C double of the Michael system has an E conformation. The mean planes of the para-fluoro phenyl rings, (C31-C36) and (C41-C46), of the terphenyl moiety and the central phenyl ring (C21-C26), enclose angles of 43.39 (12)° and 49.65 (13)°, respectively (Fig. 1).

In the crystal, two different C–H···Cl contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are observed (Fig. 2 and Table 1). These are supported by two different hydrogen atoms of the terphenyl moiety. Apart from these, a C–H···O contact involving a hydrogen atom from one of the para-fluoro phenyl ring (C41-C46) and the ketonic oxygen atom O1 is apparent (Fig. 2 and Table 1). In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C–H···F contacts is C¹₁(10)C¹₁(12) on the unary level while the C–H···O contacts necessitate a C¹₁(10) descriptor on the same level. In total, the molecules are connected to form layers lying perpendicular to the a axis (Fig. 3).

The shortest intercentroid distance between two π systems was found at 3.7547 (16) Å and is apparent between the para-fluoro phenyl ring (C41-C46) and its symmetry-generated (-x, y-1/2, -z-1/2) equivalent.

Related literature top

For pharmacological background information about terphenyls, see: Astrue (2002); Liu (2006). For the crystal structures of other terphenyl derivatives, see: Betz et al. (2011a,b,c,d,e); Samshuddin et al. (2011). For graph-set analysis, see: Etter et al. (1990); Bernstein et al. (1995).

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-chlorobenzaldehyde (0.104 g, 0.001 mol) in 30 ml of ethanol, 1 ml of a 10% sodium hydroxide solution was added and stirred at 278–283 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by slow evaporation at room temperature. The yield of the title compound was 81% (m.p.: 452 K).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along b axis of the C–H···O and C–H···Cl contacts (dashed lines) in the crystal structure of the title compound [symmetry operators: (i) x, -y + 1/2, z + 1/2; (ii) x, -y + 1/2, z - 1/2].
	Fig. 3. Molecular packing of the title compound, viewed along the b axis (displacement ellipsoids are drawn at the 50% probability level).

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

Crystal data top

C₂₈H₁₉ClF₂O₂	F(000) = 952
M_r = 460.88	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 452 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.2065 (7) Å	Cell parameters from 7266 reflections
b = 6.8651 (3) Å	θ = 2.6–28.2°
c = 22.4817 (11) Å	µ = 0.22 mm⁻¹
β = 101.406 (2)°	T = 200 K
V = 2149.32 (18) Å³	Block, yellow
Z = 4	0.40 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	5318 independent reflections
Radiation source: fine-focus sealed tube	3817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
T_min = 0.918, T_max = 0.962	k = −9→8
17828 measured reflections	l = −29→29

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0356P)² + 2.7063P] where P = (F_o² + 2F_c²)/3
5318 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₈H₁₉ClF₂O₂	V = 2149.32 (18) Å³
M_r = 460.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2065 (7) Å	µ = 0.22 mm⁻¹
b = 6.8651 (3) Å	T = 200 K
c = 22.4817 (11) Å	0.40 × 0.20 × 0.18 mm
β = 101.406 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5318 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3817 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.962	R_int = 0.051
17828 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.07	Δρ_max = 0.41 e Å⁻³
5318 reflections	Δρ_min = −0.31 e Å⁻³
299 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.32945 (5)	0.46688 (11)	0.32261 (3)	0.0424 (2)
F1	0.48872 (13)	−0.3590 (3)	0.05070 (8)	0.0542 (5)
F2	−0.02840 (13)	0.4610 (3)	−0.34871 (6)	0.0483 (4)
O1	0.21690 (15)	0.2023 (3)	0.11598 (8)	0.0394 (5)
O2	0.10962 (14)	0.6409 (3)	0.04792 (7)	0.0360 (4)
C1	0.29266 (17)	0.5306 (4)	0.18625 (10)	0.0286 (5)
H1	0.2750	0.4189	0.2065	0.034*
C2	0.27497 (18)	0.5259 (4)	0.12635 (10)	0.0308 (5)
H2	0.2916	0.6354	0.1048	0.037*
C3	0.22992 (17)	0.3548 (4)	0.09182 (10)	0.0266 (5)
C4	0.0579 (2)	0.8171 (4)	0.03123 (12)	0.0380 (6)
H4A	0.0929	0.8975	0.0068	0.057*
H4B	0.0512	0.8885	0.0679	0.057*
H4C	−0.0059	0.7863	0.0075	0.057*
C11	0.33711 (17)	0.6927 (4)	0.22443 (10)	0.0280 (5)
C12	0.35889 (17)	0.6785 (4)	0.28769 (10)	0.0283 (5)
C13	0.40353 (19)	0.8263 (4)	0.32436 (12)	0.0353 (6)
H13	0.4168	0.8114	0.3672	0.042*
C14	0.4286 (2)	0.9946 (4)	0.29868 (13)	0.0410 (7)
H14	0.4612	1.0954	0.3235	0.049*
C15	0.4060 (2)	1.0165 (4)	0.23610 (14)	0.0440 (7)
H15	0.4217	1.1341	0.2180	0.053*
C16	0.3608 (2)	0.8686 (4)	0.20019 (12)	0.0378 (6)
H16	0.3453	0.8869	0.1575	0.045*
C21	0.19968 (16)	0.3801 (4)	0.02426 (10)	0.0250 (5)
C22	0.22967 (16)	0.2553 (3)	−0.01771 (10)	0.0236 (5)
C23	0.19342 (17)	0.2854 (4)	−0.07951 (10)	0.0262 (5)
H23	0.2142	0.2030	−0.1083	0.031*
C24	0.12777 (16)	0.4327 (4)	−0.09994 (10)	0.0250 (5)
C25	0.09855 (17)	0.5559 (4)	−0.05830 (10)	0.0271 (5)
H25	0.0537	0.6570	−0.0716	0.033*
C26	0.13545 (17)	0.5300 (4)	0.00332 (10)	0.0261 (5)
C31	0.29922 (17)	0.0940 (3)	0.00053 (10)	0.0245 (5)
C32	0.38279 (17)	0.1197 (4)	0.04463 (11)	0.0301 (5)
H32	0.3961	0.2434	0.0634	0.036*
C33	0.44637 (19)	−0.0325 (4)	0.06131 (11)	0.0359 (6)
H33	0.5026	−0.0150	0.0916	0.043*
C34	0.4265 (2)	−0.2090 (4)	0.03319 (12)	0.0360 (6)
C35	0.34726 (19)	−0.2412 (4)	−0.01133 (11)	0.0332 (6)
H35	0.3361	−0.3644	−0.0307	0.040*
C36	0.28382 (18)	−0.0874 (4)	−0.02719 (11)	0.0294 (5)
H36	0.2282	−0.1067	−0.0579	0.035*
C41	0.08695 (17)	0.4497 (4)	−0.16619 (10)	0.0263 (5)
C42	0.14603 (19)	0.4464 (4)	−0.20846 (11)	0.0314 (5)
H42	0.2137	0.4398	−0.1949	0.038*
C43	0.1081 (2)	0.4526 (4)	−0.27020 (11)	0.0350 (6)
H43	0.1487	0.4518	−0.2991	0.042*
C44	0.0103 (2)	0.4598 (4)	−0.28813 (10)	0.0335 (6)
C45	−0.05083 (19)	0.4642 (4)	−0.24832 (11)	0.0342 (6)
H45	−0.1184	0.4694	−0.2625	0.041*
C46	−0.01178 (18)	0.4607 (4)	−0.18650 (11)	0.0300 (5)
H46	−0.0529	0.4659	−0.1580	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0517 (4)	0.0472 (4)	0.0245 (3)	−0.0136 (3)	−0.0019 (3)	0.0057 (3)
F1	0.0605 (11)	0.0418 (10)	0.0580 (11)	0.0263 (9)	0.0060 (9)	0.0116 (8)
F2	0.0676 (12)	0.0481 (10)	0.0226 (7)	0.0027 (9)	−0.0072 (7)	0.0013 (7)
O1	0.0562 (12)	0.0328 (11)	0.0284 (9)	−0.0035 (10)	0.0062 (8)	0.0048 (8)
O2	0.0450 (11)	0.0365 (11)	0.0255 (8)	0.0141 (9)	0.0047 (7)	−0.0039 (8)
C1	0.0295 (12)	0.0278 (13)	0.0275 (11)	0.0002 (11)	0.0030 (9)	0.0031 (10)
C2	0.0332 (13)	0.0316 (14)	0.0269 (11)	−0.0026 (12)	0.0039 (10)	0.0013 (10)
C3	0.0270 (12)	0.0284 (13)	0.0246 (11)	0.0035 (11)	0.0055 (9)	0.0019 (10)
C4	0.0452 (16)	0.0288 (15)	0.0402 (14)	0.0087 (13)	0.0093 (12)	−0.0050 (11)
C11	0.0282 (12)	0.0287 (13)	0.0264 (11)	0.0008 (11)	0.0032 (9)	−0.0009 (10)
C12	0.0254 (12)	0.0296 (14)	0.0286 (12)	0.0000 (10)	0.0021 (9)	−0.0003 (10)
C13	0.0330 (13)	0.0405 (16)	0.0299 (12)	0.0000 (12)	0.0003 (10)	−0.0079 (11)
C14	0.0370 (15)	0.0354 (16)	0.0486 (16)	−0.0036 (13)	0.0032 (12)	−0.0113 (13)
C15	0.0499 (17)	0.0293 (15)	0.0536 (17)	−0.0066 (13)	0.0118 (14)	0.0007 (13)
C16	0.0485 (16)	0.0338 (15)	0.0301 (13)	−0.0005 (13)	0.0053 (11)	0.0015 (11)
C21	0.0257 (11)	0.0252 (12)	0.0227 (10)	−0.0021 (10)	0.0013 (9)	−0.0006 (9)
C22	0.0231 (11)	0.0219 (12)	0.0246 (11)	−0.0024 (10)	0.0014 (9)	0.0005 (9)
C23	0.0262 (12)	0.0264 (13)	0.0249 (11)	0.0006 (10)	0.0027 (9)	−0.0037 (9)
C24	0.0241 (11)	0.0260 (13)	0.0233 (10)	−0.0019 (10)	0.0006 (8)	0.0001 (9)
C25	0.0270 (12)	0.0246 (13)	0.0282 (11)	0.0028 (10)	0.0014 (9)	0.0001 (10)
C26	0.0296 (12)	0.0220 (12)	0.0265 (11)	−0.0005 (10)	0.0049 (9)	−0.0021 (9)
C31	0.0278 (12)	0.0224 (12)	0.0236 (10)	0.0012 (10)	0.0062 (9)	0.0022 (9)
C32	0.0298 (13)	0.0310 (14)	0.0285 (12)	0.0004 (11)	0.0030 (10)	−0.0015 (10)
C33	0.0308 (13)	0.0434 (17)	0.0313 (12)	0.0075 (13)	0.0007 (10)	0.0044 (12)
C34	0.0398 (15)	0.0346 (15)	0.0352 (13)	0.0129 (12)	0.0111 (11)	0.0121 (11)
C35	0.0427 (15)	0.0230 (13)	0.0360 (13)	0.0007 (12)	0.0130 (11)	0.0019 (11)
C36	0.0324 (13)	0.0268 (13)	0.0287 (12)	−0.0006 (11)	0.0052 (10)	0.0007 (10)
C41	0.0309 (12)	0.0226 (12)	0.0231 (10)	0.0011 (10)	−0.0006 (9)	−0.0016 (9)
C42	0.0315 (13)	0.0312 (14)	0.0302 (12)	0.0001 (11)	0.0026 (10)	−0.0007 (11)
C43	0.0454 (16)	0.0324 (15)	0.0277 (12)	−0.0013 (13)	0.0085 (11)	−0.0002 (11)
C44	0.0496 (16)	0.0262 (13)	0.0206 (11)	0.0017 (12)	−0.0034 (10)	0.0007 (10)
C45	0.0342 (13)	0.0310 (14)	0.0321 (12)	0.0026 (12)	−0.0063 (10)	0.0001 (11)
C46	0.0304 (13)	0.0306 (14)	0.0278 (11)	0.0020 (11)	0.0026 (9)	0.0006 (10)

Geometric parameters (Å, º) top

Cl1—C12	1.741 (3)	C22—C31	1.487 (3)
F1—C34	1.364 (3)	C23—C24	1.391 (3)
F2—C44	1.364 (3)	C23—H23	0.9500
O1—C3	1.211 (3)	C24—C25	1.385 (3)
O2—C26	1.366 (3)	C24—C41	1.492 (3)
O2—C4	1.426 (3)	C25—C26	1.392 (3)
C1—C2	1.321 (3)	C25—H25	0.9500
C1—C11	1.470 (3)	C31—C36	1.390 (3)
C1—H1	0.9500	C31—C32	1.399 (3)
C2—C3	1.481 (3)	C32—C33	1.384 (4)
C2—H2	0.9500	C32—H32	0.9500
C3—C21	1.504 (3)	C33—C34	1.370 (4)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.368 (4)
C4—H4C	0.9800	C35—C36	1.388 (4)
C11—C16	1.393 (4)	C35—H35	0.9500
C11—C12	1.398 (3)	C36—H36	0.9500
C12—C13	1.380 (3)	C41—C42	1.387 (3)
C13—C14	1.369 (4)	C41—C46	1.389 (3)
C13—H13	0.9500	C42—C43	1.387 (3)
C14—C15	1.388 (4)	C42—H42	0.9500
C14—H14	0.9500	C43—C44	1.368 (4)
C15—C16	1.375 (4)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.365 (4)
C16—H16	0.9500	C45—C46	1.391 (3)
C21—C26	1.394 (3)	C45—H45	0.9500
C21—C22	1.402 (3)	C46—H46	0.9500
C22—C23	1.398 (3)

C26—O2—C4	118.60 (19)	C25—C24—C41	121.2 (2)
C2—C1—C11	126.0 (2)	C23—C24—C41	119.3 (2)
C2—C1—H1	117.0	C24—C25—C26	119.4 (2)
C11—C1—H1	117.0	C24—C25—H25	120.3
C1—C2—C3	121.9 (2)	C26—C25—H25	120.3
C1—C2—H2	119.0	O2—C26—C25	123.8 (2)
C3—C2—H2	119.0	O2—C26—C21	114.6 (2)
O1—C3—C2	122.6 (2)	C25—C26—C21	121.5 (2)
O1—C3—C21	120.9 (2)	C36—C31—C32	117.8 (2)
C2—C3—C21	116.4 (2)	C36—C31—C22	120.4 (2)
O2—C4—H4A	109.5	C32—C31—C22	121.7 (2)
O2—C4—H4B	109.5	C33—C32—C31	120.9 (2)
H4A—C4—H4B	109.5	C33—C32—H32	119.5
O2—C4—H4C	109.5	C31—C32—H32	119.5
H4A—C4—H4C	109.5	C34—C33—C32	118.6 (2)
H4B—C4—H4C	109.5	C34—C33—H33	120.7
C16—C11—C12	115.9 (2)	C32—C33—H33	120.7
C16—C11—C1	122.5 (2)	F1—C34—C35	118.8 (3)
C12—C11—C1	121.6 (2)	F1—C34—C33	118.1 (2)
C13—C12—C11	122.6 (2)	C35—C34—C33	123.1 (2)
C13—C12—Cl1	117.85 (19)	C34—C35—C36	117.6 (2)
C11—C12—Cl1	119.51 (19)	C34—C35—H35	121.2
C14—C13—C12	119.7 (2)	C36—C35—H35	121.2
C14—C13—H13	120.1	C35—C36—C31	122.0 (2)
C12—C13—H13	120.1	C35—C36—H36	119.0
C13—C14—C15	119.4 (3)	C31—C36—H36	119.0
C13—C14—H14	120.3	C42—C41—C46	119.0 (2)
C15—C14—H14	120.3	C42—C41—C24	120.9 (2)
C16—C15—C14	120.2 (3)	C46—C41—C24	120.0 (2)
C16—C15—H15	119.9	C43—C42—C41	121.1 (2)
C14—C15—H15	119.9	C43—C42—H42	119.4
C15—C16—C11	122.1 (2)	C41—C42—H42	119.4
C15—C16—H16	119.0	C44—C43—C42	117.8 (2)
C11—C16—H16	119.0	C44—C43—H43	121.1
C26—C21—C22	119.3 (2)	C42—C43—H43	121.1
C26—C21—C3	117.6 (2)	F2—C44—C45	118.1 (2)
C22—C21—C3	123.0 (2)	F2—C44—C43	118.7 (2)
C23—C22—C21	118.5 (2)	C45—C44—C43	123.2 (2)
C23—C22—C31	118.6 (2)	C44—C45—C46	118.4 (2)
C21—C22—C31	122.9 (2)	C44—C45—H45	120.8
C24—C23—C22	121.8 (2)	C46—C45—H45	120.8
C24—C23—H23	119.1	C41—C46—C45	120.5 (2)
C22—C23—H23	119.1	C41—C46—H46	119.8
C25—C24—C23	119.5 (2)	C45—C46—H46	119.8

C11—C1—C2—C3	179.9 (2)	C24—C25—C26—C21	−1.5 (4)
C1—C2—C3—O1	−8.7 (4)	C22—C21—C26—O2	178.9 (2)
C1—C2—C3—C21	170.7 (2)	C3—C21—C26—O2	1.8 (3)
C2—C1—C11—C16	4.0 (4)	C22—C21—C26—C25	1.6 (4)
C2—C1—C11—C12	−175.5 (3)	C3—C21—C26—C25	−175.6 (2)
C16—C11—C12—C13	−1.7 (4)	C23—C22—C31—C36	−43.5 (3)
C1—C11—C12—C13	177.8 (2)	C21—C22—C31—C36	137.3 (2)
C16—C11—C12—Cl1	178.4 (2)	C23—C22—C31—C32	135.0 (2)
C1—C11—C12—Cl1	−2.0 (3)	C21—C22—C31—C32	−44.2 (3)
C11—C12—C13—C14	−0.4 (4)	C36—C31—C32—C33	−1.9 (4)
Cl1—C12—C13—C14	179.5 (2)	C22—C31—C32—C33	179.6 (2)
C12—C13—C14—C15	2.0 (4)	C31—C32—C33—C34	0.8 (4)
C13—C14—C15—C16	−1.6 (4)	C32—C33—C34—F1	−178.9 (2)
C14—C15—C16—C11	−0.7 (5)	C32—C33—C34—C35	1.0 (4)
C12—C11—C16—C15	2.3 (4)	F1—C34—C35—C36	178.4 (2)
C1—C11—C16—C15	−177.3 (3)	C33—C34—C35—C36	−1.5 (4)
O1—C3—C21—C26	122.1 (3)	C34—C35—C36—C31	0.2 (4)
C2—C3—C21—C26	−57.3 (3)	C32—C31—C36—C35	1.4 (4)
O1—C3—C21—C22	−54.9 (3)	C22—C31—C36—C35	180.0 (2)
C2—C3—C21—C22	125.6 (3)	C25—C24—C41—C42	134.0 (3)
C26—C21—C22—C23	−0.3 (3)	C23—C24—C41—C42	−48.6 (3)
C3—C21—C22—C23	176.7 (2)	C25—C24—C41—C46	−48.7 (3)
C26—C21—C22—C31	178.9 (2)	C23—C24—C41—C46	128.6 (3)
C3—C21—C22—C31	−4.1 (4)	C46—C41—C42—C43	−0.4 (4)
C21—C22—C23—C24	−1.1 (4)	C24—C41—C42—C43	176.8 (2)
C31—C22—C23—C24	179.7 (2)	C41—C42—C43—C44	−0.7 (4)
C22—C23—C24—C25	1.3 (4)	C42—C43—C44—F2	−178.4 (2)
C22—C23—C24—C41	−176.1 (2)	C42—C43—C44—C45	1.0 (4)
C23—C24—C25—C26	0.0 (4)	F2—C44—C45—C46	179.3 (2)
C41—C24—C25—C26	177.4 (2)	C43—C44—C45—C46	−0.1 (4)
C4—O2—C26—C25	−13.5 (4)	C42—C41—C46—C45	1.4 (4)
C4—O2—C26—C21	169.2 (2)	C24—C41—C46—C45	−175.9 (2)
C24—C25—C26—O2	−178.5 (2)	C44—C45—C46—C41	−1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···Cl1ⁱ	0.95	2.73	3.641 (2)	161
C33—H33···Cl1ⁱⁱ	0.95	2.76	3.697 (3)	170
C43—H43···O1ⁱ	0.95	2.54	3.411 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₂₈H₁₉ClF₂O₂
M_r	460.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	14.2065 (7), 6.8651 (3), 22.4817 (11)
β (°)	101.406 (2)
V (Å³)	2149.32 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.918, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	17828, 5318, 3817
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.141, 1.07
No. of reflections	5318
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.31

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···Cl1ⁱ	0.95	2.73	3.641 (2)	161
C33—H33···Cl1ⁱⁱ	0.95	2.76	3.697 (3)	170
C43—H43···O1ⁱ	0.95	2.54	3.411 (3)	153

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

Acknowledgements

BN thanks the UGC for financial assistance through SAP and BSR one-time grants for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

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Volume 68| Part 5| May 2012| Pages o1538-o1539

doi:10.1107/S1600536812017692

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

(E)-3-(2-Chloro­phen­yl)-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

Acknowledgements

References

organic compounds

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