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

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

doi:10.1107/S1600536811045806

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3179-o3180

https://doi.org/10.1107/S1600536811045806

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

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

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

(Received 12 October 2011; accepted 31 October 2011; online 5 November 2011)

In the title compound, C₂₈H₁₉F₂NO₄, a polysubstituted terphenyl derivative bearing a Michael system, the C=C double bond has an E configuration. Two C—H⋯F contacts connect molecules into inversion dimers. In addition, a C–H⋯π as well as a C–F⋯π contact can be identified. The shortest centroid–centroid distance between two aromatic rings is 3.9535 (8) Å, between one of the para-fluorobenzene rings and its symmetry-generated equivalent.

Related literature

For the pharmacological importance of terphenyls, see: Liu (2006 ) and of chalcones, see: Dhar (1981 ); Dimmock et al. (1999 ); Satyanarayana et al. (2004 ). For our work on the synthesis of different chalcone derivatives, see: Samshuddin et al. (2011a ,b ); Fun et al. (2010a ,b ); Jasinski et al. (2010a ,b ); Baktır et al. (2011a ,b ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₁₉F₂NO₄
M_r = 471.44
Monoclinic, P 2₁ /c
a = 23.3751 (7) Å
b = 6.9098 (2) Å
c = 13.7879 (5) Å
β = 99.243 (2)°
V = 2198.07 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 200 K
0.58 × 0.44 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
37111 measured reflections
5462 independent reflections
4899 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.114
S = 1.05
5462 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F1ⁱ	0.95	2.54	3.2165 (17)	129
C33—H33⋯Cg1ⁱⁱ	0.95	2.91	3.4748 (15)	119
C24—F1⋯Cg1ⁱⁱⁱ	1.36 (1)	3.95 (1)	4.8373 (15)	123 (1)
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x, y-1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811045806/fj2465sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045806/fj2465Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045806/fj2465Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045806/fj2465Isup4.cml

checkCIF report

Comment top

Chalcones constitute an important family of substances belonging to flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activity and structural characteristics. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). In recent years, it has been reported that some terphenyls exhibit considerable biological activities (e.g. being potent anticoagulants, immunosuppressants, antithrombotics, neuroprotectives, specific 5-lipoxygenase inhibitors) and showing cytotoxic activities (Liu, 2006). In view of the pharmacological importance of terphenyls and chalcones, and in continuation of our work on synthesis of various derivatives of 4,4'-difluoro chalcone (Samshuddin et al., 2011a/b, Fun et al., 2010a/b, Jasinski et al., 2010a/b, Baktır et al., 2011a/b), the molecular and crystal structure of the title compound is reported.

The C=C double of the Michael system is (E)-configured. The least-squares planes defined by the carbon atoms of the para-fluoro phenyl rings of the terphenyl moiety and its central phenyl ring enclose angles of 40.43 (6)° and 43.99 (6)°, respectively. The plane defined by the atoms of the nitro group is tilted by 13.56 (19)° with respect to the plane of the aromatic system it is bonded to (Fig. 1).

In the crystal, C–H···F contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the corresponding atoms are observed. These are supported by one of the hydrogen atoms in ortho position to a fluorine atom whose symmetry-generated equivalent acts as acceptor for this type of contact. In total, the molecules are connected to centrosymmetric dimers (Fig. 2). In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C–H···F contacts is R²₂(8) on the unitary level. In addition, a C–H···π as well as a C–F···π contact can be identified. The shortest intercentroid distance between two aromatic systems is apparent between two of the para-fluoro phenyl moieties that are also part of the C–H···F contacts and was measured at 3.9535 (8) Å. Details about metrical parameters of the intermolecular contacts and their symmetry can be found in Table 1.

The packing of the title compound in the crystal is shown in Figure 3.

Related literature top

For the pharmacological importance of terphenyls, see: Liu (2006) and of chalcones, see: Dhar (1981); Dimmock et al. (1999); Satyanarayana et al. (2004). For our work on the synthesis of different chalcone derivatives, see: Samshuddin et al. (2011a,b); Fun et al. (2010a,b); Jasinski et al. (2010a,b); Baktır et al. (2011a,b). For graph-set analysis of hydrogen bonds, 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 (3.38 g, 0.01 mol) and 4-nitrobenzaldehyde (1.51 g, 0.01 mol) in 40 ml of ethanol, 10 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 (yield: 80%). Single crystals suitable for the X-ray diffraction study were grown from DMF–ethanol (v:v 1:1) by slow evaporation at room temperature.

Structure description top

The packing of the title compound in the crystal is shown in Figure 3.

For the pharmacological importance of terphenyls, see: Liu (2006) and of chalcones, see: Dhar (1981); Dimmock et al. (1999); Satyanarayana et al. (2004). For our work on the synthesis of different chalcone derivatives, see: Samshuddin et al. (2011a,b); Fun et al. (2010a,b); Jasinski et al. (2010a,b); Baktır et al. (2011a,b). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

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 compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 1 0]. Symmetry operator: ⁱ -x + 1, -y + 2, -z.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

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

Crystal data top

C₂₈H₁₉F₂NO₄	F(000) = 976
M_r = 471.44	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 489 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.3751 (7) Å	Cell parameters from 9792 reflections
b = 6.9098 (2) Å	θ = 2.7–28.4°
c = 13.7879 (5) Å	µ = 0.11 mm⁻¹
β = 99.243 (2)°	T = 200 K
V = 2198.07 (12) Å³	Block, yellow
Z = 4	0.58 × 0.44 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	4899 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 28.4°, θ_min = 1.8°
φ and ω scans	h = −31→31
37111 measured reflections	k = −9→9
5462 independent reflections	l = −18→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0442P)² + 1.0552P] where P = (F_o² + 2F_c²)/3
5462 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₈H₁₉F₂NO₄	V = 2198.07 (12) Å³
M_r = 471.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 23.3751 (7) Å	µ = 0.11 mm⁻¹
b = 6.9098 (2) Å	T = 200 K
c = 13.7879 (5) Å	0.58 × 0.44 × 0.17 mm
β = 99.243 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4899 reflections with I > 2σ(I)
37111 measured reflections	R_int = 0.026
5462 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
5462 reflections	Δρ_min = −0.24 e Å⁻³
317 parameters

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

	x	y	z	U_iso*/U_eq
F1	0.54918 (4)	0.89243 (16)	0.09405 (8)	0.0577 (3)
F2	0.14304 (5)	0.02099 (15)	0.26896 (8)	0.0585 (3)
O1	0.25621 (5)	0.57681 (15)	0.56774 (8)	0.0428 (2)
O2	0.32555 (5)	1.02608 (15)	0.54905 (8)	0.0426 (2)
O3	−0.01724 (6)	1.5042 (2)	0.61968 (11)	0.0651 (4)
O4	−0.06990 (5)	1.2537 (2)	0.63545 (13)	0.0765 (5)
N1	−0.02455 (6)	1.3295 (2)	0.62244 (10)	0.0480 (3)
C1	0.25169 (5)	0.72612 (19)	0.52066 (9)	0.0310 (3)
C2	0.20726 (6)	0.8734 (2)	0.53077 (10)	0.0346 (3)
H2	0.2095	0.9969	0.5013	0.042*
C3	0.16442 (6)	0.8363 (2)	0.58026 (10)	0.0348 (3)
H3	0.1650	0.7142	0.6121	0.042*
C4	0.35123 (8)	1.2132 (2)	0.55848 (11)	0.0460 (3)
H4A	0.3935	1.2006	0.5682	0.069*
H4B	0.3397	1.2798	0.6151	0.069*
H4C	0.3382	1.2882	0.4987	0.069*
C11	0.29155 (5)	0.76687 (18)	0.44743 (9)	0.0291 (2)
C12	0.33024 (6)	0.92135 (18)	0.46656 (9)	0.0314 (3)
C13	0.37199 (5)	0.95644 (19)	0.40751 (9)	0.0314 (3)
H13	0.3990	1.0591	0.4228	0.038*
C14	0.37401 (5)	0.83985 (18)	0.32563 (9)	0.0287 (2)
C15	0.33356 (5)	0.69187 (18)	0.30343 (9)	0.0284 (2)
H15	0.3338	0.6170	0.2457	0.034*
C16	0.29257 (5)	0.65097 (17)	0.36424 (9)	0.0274 (2)
C21	0.41994 (5)	0.86685 (17)	0.26396 (9)	0.0292 (2)
C22	0.47750 (6)	0.89612 (19)	0.30685 (10)	0.0338 (3)
H22	0.4870	0.9087	0.3762	0.041*
C23	0.52104 (6)	0.9071 (2)	0.24956 (11)	0.0386 (3)
H23	0.5602	0.9277	0.2787	0.046*
C24	0.50613 (6)	0.8877 (2)	0.14999 (11)	0.0394 (3)
C25	0.45022 (7)	0.8625 (2)	0.10411 (11)	0.0410 (3)
H25	0.4413	0.8524	0.0346	0.049*
C26	0.40697 (6)	0.8522 (2)	0.16222 (10)	0.0356 (3)
H26	0.3678	0.8348	0.1319	0.043*
C31	0.25194 (5)	0.48643 (18)	0.33831 (9)	0.0278 (2)
C32	0.27220 (6)	0.31378 (19)	0.30383 (10)	0.0331 (3)
H32	0.3119	0.3038	0.2968	0.040*
C33	0.23598 (6)	0.1566 (2)	0.27957 (10)	0.0384 (3)
H33	0.2501	0.0399	0.2556	0.046*
C34	0.17884 (6)	0.1751 (2)	0.29133 (11)	0.0390 (3)
C35	0.15653 (6)	0.3426 (2)	0.32347 (10)	0.0381 (3)
H35	0.1168	0.3510	0.3300	0.046*
C36	0.19314 (5)	0.4991 (2)	0.34611 (10)	0.0329 (3)
H36	0.1781	0.6168	0.3672	0.039*
C41	0.11626 (6)	0.9660 (2)	0.59044 (9)	0.0334 (3)
C42	0.11732 (6)	1.1622 (2)	0.56648 (11)	0.0388 (3)
H42	0.1500	1.2140	0.5423	0.047*
C43	0.07152 (6)	1.2819 (2)	0.57750 (11)	0.0407 (3)
H43	0.0725	1.4158	0.5623	0.049*
C44	0.02418 (6)	1.2015 (2)	0.61122 (10)	0.0378 (3)
C45	0.02118 (6)	1.0089 (2)	0.63473 (11)	0.0414 (3)
H45	−0.0122	0.9574	0.6568	0.050*
C46	0.06796 (6)	0.8922 (2)	0.62547 (11)	0.0395 (3)
H46	0.0672	0.7595	0.6433	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0536 (6)	0.0593 (6)	0.0704 (6)	0.0013 (5)	0.0407 (5)	0.0106 (5)
F2	0.0576 (6)	0.0439 (5)	0.0721 (7)	−0.0193 (4)	0.0047 (5)	−0.0043 (5)
O1	0.0448 (5)	0.0411 (5)	0.0462 (6)	0.0121 (4)	0.0186 (4)	0.0126 (4)
O2	0.0513 (6)	0.0372 (5)	0.0438 (5)	−0.0048 (4)	0.0208 (5)	−0.0128 (4)
O3	0.0632 (8)	0.0562 (8)	0.0811 (9)	0.0269 (6)	0.0276 (7)	0.0082 (7)
O4	0.0345 (6)	0.0864 (11)	0.1117 (12)	0.0079 (6)	0.0207 (7)	−0.0264 (9)
N1	0.0370 (6)	0.0639 (9)	0.0438 (7)	0.0154 (6)	0.0084 (5)	−0.0087 (6)
C1	0.0300 (6)	0.0330 (6)	0.0312 (6)	0.0043 (5)	0.0084 (5)	−0.0003 (5)
C2	0.0362 (6)	0.0341 (6)	0.0355 (6)	0.0077 (5)	0.0118 (5)	0.0020 (5)
C3	0.0340 (6)	0.0346 (7)	0.0373 (6)	0.0057 (5)	0.0102 (5)	0.0005 (5)
C4	0.0619 (9)	0.0356 (7)	0.0392 (7)	0.0010 (7)	0.0041 (7)	−0.0078 (6)
C11	0.0281 (5)	0.0288 (6)	0.0316 (6)	0.0060 (5)	0.0085 (4)	0.0021 (5)
C12	0.0337 (6)	0.0283 (6)	0.0331 (6)	0.0051 (5)	0.0082 (5)	−0.0022 (5)
C13	0.0303 (6)	0.0278 (6)	0.0368 (6)	0.0015 (5)	0.0071 (5)	−0.0007 (5)
C14	0.0266 (5)	0.0281 (6)	0.0322 (6)	0.0056 (4)	0.0076 (4)	0.0032 (5)
C15	0.0287 (5)	0.0277 (6)	0.0300 (5)	0.0044 (4)	0.0076 (4)	−0.0005 (4)
C16	0.0259 (5)	0.0254 (5)	0.0313 (6)	0.0057 (4)	0.0063 (4)	0.0019 (4)
C21	0.0293 (6)	0.0244 (5)	0.0353 (6)	0.0026 (4)	0.0099 (5)	0.0021 (5)
C22	0.0324 (6)	0.0314 (6)	0.0383 (6)	−0.0004 (5)	0.0078 (5)	0.0018 (5)
C23	0.0304 (6)	0.0328 (7)	0.0544 (8)	−0.0012 (5)	0.0123 (6)	0.0049 (6)
C24	0.0419 (7)	0.0304 (6)	0.0522 (8)	0.0017 (5)	0.0264 (6)	0.0075 (6)
C25	0.0490 (8)	0.0402 (7)	0.0370 (7)	−0.0005 (6)	0.0166 (6)	0.0052 (6)
C26	0.0344 (6)	0.0365 (7)	0.0367 (7)	0.0003 (5)	0.0082 (5)	0.0047 (5)
C31	0.0278 (5)	0.0292 (6)	0.0270 (5)	0.0034 (4)	0.0061 (4)	0.0025 (4)
C32	0.0338 (6)	0.0314 (6)	0.0354 (6)	0.0047 (5)	0.0093 (5)	0.0008 (5)
C33	0.0464 (8)	0.0290 (6)	0.0400 (7)	0.0031 (5)	0.0074 (6)	−0.0016 (5)
C34	0.0422 (7)	0.0347 (7)	0.0389 (7)	−0.0082 (6)	0.0026 (5)	0.0026 (5)
C35	0.0297 (6)	0.0443 (8)	0.0402 (7)	−0.0026 (5)	0.0057 (5)	0.0018 (6)
C36	0.0287 (6)	0.0341 (6)	0.0364 (6)	0.0039 (5)	0.0071 (5)	−0.0005 (5)
C41	0.0314 (6)	0.0382 (7)	0.0322 (6)	0.0051 (5)	0.0100 (5)	−0.0004 (5)
C42	0.0365 (7)	0.0412 (7)	0.0420 (7)	0.0062 (6)	0.0164 (5)	0.0044 (6)
C43	0.0423 (7)	0.0414 (7)	0.0405 (7)	0.0105 (6)	0.0124 (6)	0.0039 (6)
C44	0.0307 (6)	0.0505 (8)	0.0324 (6)	0.0105 (6)	0.0055 (5)	−0.0059 (6)
C45	0.0319 (6)	0.0518 (9)	0.0433 (7)	−0.0012 (6)	0.0142 (5)	−0.0064 (6)
C46	0.0383 (7)	0.0389 (7)	0.0440 (7)	0.0006 (6)	0.0146 (6)	−0.0018 (6)

Geometric parameters (Å, º) top

F1—C24	1.3630 (15)	C22—C23	1.3870 (18)
F2—C34	1.3586 (16)	C22—H22	0.9500
O1—C1	1.2145 (16)	C23—C24	1.368 (2)
O2—C12	1.3673 (15)	C23—H23	0.9500
O2—C4	1.4230 (18)	C24—C25	1.368 (2)
O3—N1	1.221 (2)	C25—C26	1.3889 (18)
O4—N1	1.2209 (19)	C25—H25	0.9500
N1—C44	1.4698 (18)	C26—H26	0.9500
C1—C2	1.4764 (17)	C31—C32	1.3949 (17)
C1—C11	1.5063 (16)	C31—C36	1.3985 (17)
C2—C3	1.3243 (18)	C32—C33	1.3848 (19)
C2—H2	0.9500	C32—H32	0.9500
C3—C41	1.4630 (17)	C33—C34	1.377 (2)
C3—H3	0.9500	C33—H33	0.9500
C4—H4A	0.9800	C34—C35	1.372 (2)
C4—H4B	0.9800	C35—C36	1.3832 (19)
C4—H4C	0.9800	C35—H35	0.9500
C11—C12	1.3965 (18)	C36—H36	0.9500
C11—C16	1.4022 (17)	C41—C46	1.3939 (19)
C12—C13	1.3890 (17)	C41—C42	1.397 (2)
C13—C14	1.3939 (17)	C42—C43	1.3802 (19)
C13—H13	0.9500	C42—H42	0.9500
C14—C15	1.3930 (17)	C43—C44	1.384 (2)
C14—C21	1.4844 (16)	C43—H43	0.9500
C15—C16	1.3997 (16)	C44—C45	1.374 (2)
C15—H15	0.9500	C45—C46	1.381 (2)
C16—C31	1.4877 (17)	C45—H45	0.9500
C21—C26	1.3905 (18)	C46—H46	0.9500
C21—C22	1.3948 (18)

C12—O2—C4	117.90 (11)	F1—C24—C23	118.25 (14)
O4—N1—O3	123.89 (14)	F1—C24—C25	118.59 (14)
O4—N1—C44	117.61 (15)	C23—C24—C25	123.16 (12)
O3—N1—C44	118.49 (14)	C24—C25—C26	118.00 (13)
O1—C1—C2	122.49 (12)	C24—C25—H25	121.0
O1—C1—C11	120.47 (11)	C26—C25—H25	121.0
C2—C1—C11	117.04 (11)	C25—C26—C21	121.16 (13)
C3—C2—C1	121.13 (13)	C25—C26—H26	119.4
C3—C2—H2	119.4	C21—C26—H26	119.4
C1—C2—H2	119.4	C32—C31—C36	118.13 (12)
C2—C3—C41	126.04 (13)	C32—C31—C16	119.80 (11)
C2—C3—H3	117.0	C36—C31—C16	122.07 (11)
C41—C3—H3	117.0	C33—C32—C31	121.69 (12)
O2—C4—H4A	109.5	C33—C32—H32	119.2
O2—C4—H4B	109.5	C31—C32—H32	119.2
H4A—C4—H4B	109.5	C34—C33—C32	117.75 (13)
O2—C4—H4C	109.5	C34—C33—H33	121.1
H4A—C4—H4C	109.5	C32—C33—H33	121.1
H4B—C4—H4C	109.5	F2—C34—C35	118.84 (13)
C12—C11—C16	119.70 (11)	F2—C34—C33	118.30 (13)
C12—C11—C1	117.89 (11)	C35—C34—C33	122.85 (13)
C16—C11—C1	122.35 (11)	C34—C35—C36	118.63 (12)
O2—C12—C13	123.57 (12)	C34—C35—H35	120.7
O2—C12—C11	115.19 (11)	C36—C35—H35	120.7
C13—C12—C11	121.16 (11)	C35—C36—C31	120.91 (12)
C12—C13—C14	119.49 (12)	C35—C36—H36	119.5
C12—C13—H13	120.3	C31—C36—H36	119.5
C14—C13—H13	120.3	C46—C41—C42	118.89 (12)
C15—C14—C13	119.48 (11)	C46—C41—C3	119.20 (13)
C15—C14—C21	119.62 (11)	C42—C41—C3	121.91 (12)
C13—C14—C21	120.87 (11)	C43—C42—C41	120.79 (13)
C14—C15—C16	121.49 (11)	C43—C42—H42	119.6
C14—C15—H15	119.3	C41—C42—H42	119.6
C16—C15—H15	119.3	C42—C43—C44	118.22 (14)
C15—C16—C11	118.55 (11)	C42—C43—H43	120.9
C15—C16—C31	118.84 (11)	C44—C43—H43	120.9
C11—C16—C31	122.61 (11)	C45—C44—C43	122.82 (13)
C26—C21—C22	118.52 (12)	C45—C44—N1	119.22 (13)
C26—C21—C14	120.55 (11)	C43—C44—N1	117.96 (14)
C22—C21—C14	120.83 (11)	C44—C45—C46	118.19 (13)
C23—C22—C21	120.84 (13)	C44—C45—H45	120.9
C23—C22—H22	119.6	C46—C45—H45	120.9
C21—C22—H22	119.6	C45—C46—C41	121.07 (14)
C24—C23—C22	118.31 (13)	C45—C46—H46	119.5
C24—C23—H23	120.8	C41—C46—H46	119.5
C22—C23—H23	120.8

O1—C1—C2—C3	−10.8 (2)	C23—C24—C25—C26	−1.4 (2)
C11—C1—C2—C3	168.41 (13)	C24—C25—C26—C21	0.0 (2)
C1—C2—C3—C41	−176.23 (13)	C22—C21—C26—C25	1.2 (2)
O1—C1—C11—C12	−114.27 (15)	C14—C21—C26—C25	−175.06 (12)
C2—C1—C11—C12	66.55 (15)	C15—C16—C31—C32	41.00 (16)
O1—C1—C11—C16	62.98 (18)	C11—C16—C31—C32	−138.88 (12)
C2—C1—C11—C16	−116.20 (13)	C15—C16—C31—C36	−138.17 (12)
C4—O2—C12—C13	20.49 (19)	C11—C16—C31—C36	41.95 (17)
C4—O2—C12—C11	−162.74 (12)	C36—C31—C32—C33	−1.30 (19)
C16—C11—C12—O2	179.64 (11)	C16—C31—C32—C33	179.50 (12)
C1—C11—C12—O2	−3.03 (17)	C31—C32—C33—C34	−0.5 (2)
C16—C11—C12—C13	−3.51 (18)	C32—C33—C34—F2	−179.18 (12)
C1—C11—C12—C13	173.82 (11)	C32—C33—C34—C35	1.6 (2)
O2—C12—C13—C14	178.94 (12)	F2—C34—C35—C36	−179.97 (12)
C11—C12—C13—C14	2.35 (19)	C33—C34—C35—C36	−0.7 (2)
C12—C13—C14—C15	1.00 (18)	C34—C35—C36—C31	−1.2 (2)
C12—C13—C14—C21	−176.80 (11)	C32—C31—C36—C35	2.18 (19)
C13—C14—C15—C16	−3.23 (18)	C16—C31—C36—C35	−178.64 (12)
C21—C14—C15—C16	174.59 (11)	C2—C3—C41—C46	165.67 (14)
C14—C15—C16—C11	2.07 (17)	C2—C3—C41—C42	−14.6 (2)
C14—C15—C16—C31	−177.81 (11)	C46—C41—C42—C43	0.2 (2)
C12—C11—C16—C15	1.28 (17)	C3—C41—C42—C43	−179.47 (13)
C1—C11—C16—C15	−175.93 (11)	C41—C42—C43—C44	−1.1 (2)
C12—C11—C16—C31	−178.84 (11)	C42—C43—C44—C45	0.5 (2)
C1—C11—C16—C31	3.96 (18)	C42—C43—C44—N1	−179.77 (13)
C15—C14—C21—C26	41.97 (17)	O4—N1—C44—C45	−12.8 (2)
C13—C14—C21—C26	−140.23 (13)	O3—N1—C44—C45	166.21 (15)
C15—C14—C21—C22	−134.25 (13)	O4—N1—C44—C43	167.52 (15)
C13—C14—C21—C22	43.55 (17)	O3—N1—C44—C43	−13.5 (2)
C26—C21—C22—C23	−1.07 (19)	C43—C44—C45—C46	1.0 (2)
C14—C21—C22—C23	175.23 (12)	N1—C44—C45—C46	−178.73 (13)
C21—C22—C23—C24	−0.3 (2)	C44—C45—C46—C41	−1.9 (2)
C22—C23—C24—F1	−177.96 (12)	C42—C41—C46—C45	1.3 (2)
C22—C23—C24—C25	1.6 (2)	C3—C41—C46—C45	−178.97 (13)
F1—C24—C25—C26	178.13 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F1ⁱ	0.95	2.54	3.2165 (17)	129
C33—H33···Cg1ⁱⁱ	0.95	2.91	3.4748 (15)	119
C24—F1···Cg1ⁱⁱⁱ	1.36 (1)	3.95 (1)	4.8373 (15)	123 (1)

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

Experimental details

Crystal data
Chemical formula	C₂₈H₁₉F₂NO₄
M_r	471.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	23.3751 (7), 6.9098 (2), 13.7879 (5)
β (°)	99.243 (2)
V (Å³)	2198.07 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.58 × 0.44 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	37111, 5462, 4899
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.114, 1.05
No. of reflections	5462
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

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

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F1ⁱ	0.95	2.54	3.2165 (17)	129
C33—H33···Cg1ⁱⁱ	0.95	2.91	3.4748 (15)	119
C24—F1···Cg1ⁱⁱⁱ	1.3630 (15)	3.9512 (12)	4.8373 (15)	123.40 (8)

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

References

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Volume 67| Part 12| December 2011| Pages o3179-o3180

https://doi.org/10.1107/S1600536811045806

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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