Literature DB >> 22347112

(2E)-1-(2,6-Dichloro-3-fluoro-phen-yl)-3-(4-fluoro-phen-yl)prop-2-en-1-one.

Richard Betz, Thomas Gerber, Eric Hosten, Aletti S Praveen, Hemmige S Yathirajan, Badiadka Narayana.

Abstract

In the title compound, C(15)H(8)Cl(2)F(2)O, the C=C double bond is in the E configuration. In the cyrstal, C-H⋯O hydrogen bonds connect the mol-ecules into chains along the c axis. A π-π inter-action of 3.628 (1) Å is also observed between two polyhalogenated benzene rings. The dichloro-substituted ring exhibits partial disorder over two sets of sites, with site-occupancy factors of 0.573 (3) and 0.427 (3).

Entities: Chemical Disease Gene

Year: 2012 PMID： 22347112 PMCID： PMC3275256 DOI： 10.1107/S1600536812002589

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For pharmaceutical background to chalcones, see: Nielsen et al. (2004 ▶); Modzelewska et al. (2006 ▶); Nowakowska (2007 ▶); Ni et al. (2004 ▶). For related structures, see: Yathirajan et al. (2006 ▶, 2007 ▶); Betz et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H8Cl2F2O M = 313.11 Monoclinic, a = 12.2311 (3) Å b = 10.3115 (2) Å c = 11.2468 (3) Å β = 108.935 (1)° V = 1341.70 (6) Å3 Z = 4 Mo Kα radiation μ = 0.50 mm−1 T = 200 K 0.48 × 0.34 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.825, T max = 1.000 12634 measured reflections 3328 independent reflections 2724 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.092 S = 1.06 3328 reflections 191 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.25 e Å−3 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 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002589/wn2465sup1.cif Supplementary material file. DOI: 10.1107/S1600536812002589/wn2465Isup2.cdx Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002589/wn2465Isup3.hkl Supplementary material file. DOI: 10.1107/S1600536812002589/wn2465Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₈Cl₂F₂O	F(000) = 632
M_r = 313.11	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 421–424 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.2311 (3) Å	Cell parameters from 7019 reflections
b = 10.3115 (2) Å	θ = 2.7–28.2°
c = 11.2468 (3) Å	µ = 0.50 mm⁻¹
β = 108.935 (1)°	T = 200 K
V = 1341.70 (6) Å³	Block, colourless
Z = 4	0.48 × 0.34 × 0.27 mm

Bruker APEXII CCD diffractometer	3328 independent reflections
Radiation source: fine-focus sealed tube	2724 reflections with I > 2σ(I)
graphite	R_int = 0.015
φ and ω scans	θ_max = 28.3°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.825, T_max = 1.000	k = −12→13
12634 measured reflections	l = −13→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0346P)² + 0.5003P] where P = (F_o² + 2F_c²)/3
3328 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.55532 (4)	0.18042 (5)	0.01581 (4)	0.05973 (14)
Cl2	0.18584 (5)	0.50107 (5)	−0.10590 (5)	0.06391 (15)
F1	−0.02753 (11)	−0.32385 (11)	−0.03660 (13)	0.0767 (4)
O1	0.33883 (11)	0.32276 (11)	−0.25385 (9)	0.0498 (3)
C1	0.23362 (12)	0.10980 (13)	−0.06621 (12)	0.0366 (3)
H1	0.2685	0.1527	0.0117	0.044*
C2	0.25296 (12)	0.16144 (14)	−0.16699 (12)	0.0378 (3)
H2	0.2198	0.1204	−0.2462	0.045*
C3	0.32232 (13)	0.27733 (14)	−0.16076 (12)	0.0380 (3)
C11	0.16497 (12)	−0.00496 (13)	−0.06298 (13)	0.0362 (3)
C12	0.16714 (14)	−0.05235 (15)	0.05394 (14)	0.0435 (3)
H12	0.2129	−0.0095	0.1282	0.052*
C13	0.10377 (16)	−0.16073 (16)	0.06360 (16)	0.0522 (4)
H13	0.1068	−0.1939	0.1434	0.063*
C14	0.03673 (15)	−0.21884 (16)	−0.04488 (18)	0.0522 (4)
C15	0.03053 (15)	−0.17524 (16)	−0.16235 (17)	0.0515 (4)
H15	−0.0173	−0.2177	−0.2358	0.062*
C16	0.09524 (14)	−0.06845 (15)	−0.17128 (14)	0.0449 (3)
H16	0.0925	−0.0375	−0.2518	0.054*
C21	0.37356 (13)	0.34472 (13)	−0.03476 (12)	0.0388 (3)
C22	0.31594 (15)	0.44789 (15)	−0.00230 (14)	0.0448 (3)
C24	0.46503 (18)	0.47039 (18)	0.19724 (16)	0.0586 (5)
H24	0.4956	0.5126	0.2762	0.070*
C26	0.47854 (14)	0.30709 (15)	0.05110 (13)	0.0434 (3)
C231	0.36195 (18)	0.50942 (16)	0.11341 (16)	0.0545 (5)	0.573 (3)
F231	0.3031 (2)	0.60294 (18)	0.14524 (19)	0.0723 (7)	0.573 (3)
C251	0.52385 (16)	0.36950 (18)	0.16607 (15)	0.0541 (5)	0.573 (3)
H251	0.5959	0.3423	0.2235	0.065*	0.573 (3)
C232	0.36195 (18)	0.50942 (16)	0.11341 (16)	0.0545 (5)	0.427 (3)
H252	0.3212	0.5795	0.1344	0.065*	0.427 (3)
C252	0.52385 (16)	0.36950 (18)	0.16607 (15)	0.0541 (5)	0.427 (3)
F232	0.6202 (2)	0.3318 (3)	0.2413 (2)	0.0763 (10)	0.427 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0634 (3)	0.0683 (3)	0.0456 (2)	0.0139 (2)	0.01502 (18)	0.00247 (19)
Cl2	0.0770 (3)	0.0586 (3)	0.0613 (3)	0.0189 (2)	0.0295 (2)	0.0032 (2)
F1	0.0894 (8)	0.0584 (7)	0.0933 (9)	−0.0277 (6)	0.0450 (7)	−0.0037 (6)
O1	0.0714 (7)	0.0513 (6)	0.0305 (5)	−0.0051 (5)	0.0216 (5)	0.0038 (4)
C1	0.0447 (7)	0.0352 (7)	0.0304 (6)	0.0025 (6)	0.0129 (5)	−0.0027 (5)
C2	0.0467 (7)	0.0392 (7)	0.0282 (6)	0.0018 (6)	0.0131 (5)	−0.0042 (5)
C3	0.0492 (8)	0.0386 (7)	0.0281 (6)	0.0042 (6)	0.0148 (5)	0.0012 (5)
C11	0.0419 (7)	0.0353 (7)	0.0345 (6)	0.0049 (5)	0.0165 (6)	−0.0011 (5)
C12	0.0533 (8)	0.0427 (8)	0.0367 (7)	0.0006 (7)	0.0178 (6)	−0.0004 (6)
C13	0.0643 (10)	0.0490 (9)	0.0503 (9)	−0.0021 (8)	0.0282 (8)	0.0066 (7)
C14	0.0563 (9)	0.0412 (8)	0.0672 (10)	−0.0065 (7)	0.0313 (8)	−0.0042 (7)
C15	0.0550 (9)	0.0502 (9)	0.0529 (9)	−0.0085 (7)	0.0226 (7)	−0.0146 (7)
C16	0.0520 (8)	0.0474 (8)	0.0379 (7)	−0.0026 (7)	0.0182 (6)	−0.0062 (6)
C21	0.0541 (8)	0.0370 (7)	0.0301 (6)	−0.0070 (6)	0.0202 (6)	0.0002 (5)
C22	0.0640 (9)	0.0382 (7)	0.0395 (7)	−0.0061 (7)	0.0267 (7)	−0.0007 (6)
C24	0.0836 (13)	0.0601 (10)	0.0386 (8)	−0.0307 (10)	0.0289 (9)	−0.0147 (7)
C26	0.0552 (9)	0.0471 (8)	0.0319 (7)	−0.0070 (7)	0.0198 (6)	0.0007 (6)
C231	0.0868 (13)	0.0428 (8)	0.0477 (9)	−0.0151 (8)	0.0407 (9)	−0.0105 (7)
F231	0.1165 (18)	0.0509 (11)	0.0629 (12)	0.0040 (10)	0.0478 (12)	−0.0140 (8)
C251	0.0628 (10)	0.0656 (11)	0.0349 (8)	−0.0214 (8)	0.0175 (7)	−0.0026 (7)
C232	0.0868 (13)	0.0428 (8)	0.0477 (9)	−0.0151 (8)	0.0407 (9)	−0.0105 (7)
C252	0.0628 (10)	0.0656 (11)	0.0349 (8)	−0.0214 (8)	0.0175 (7)	−0.0026 (7)
F232	0.0659 (17)	0.113 (2)	0.0383 (13)	−0.0239 (16)	0.0011 (11)	−0.0047 (13)

Cl1—C26	1.7284 (16)	C13—H13	0.9500
Cl2—C22	1.7284 (18)	C14—C15	1.374 (2)
F1—C14	1.3588 (18)	C15—C16	1.379 (2)
O1—C3	1.2220 (16)	C15—H15	0.9500
C1—C2	1.3410 (19)	C16—H16	0.9500
C1—C11	1.4582 (19)	C21—C26	1.388 (2)
C1—H1	0.9500	C21—C22	1.389 (2)
C2—C3	1.454 (2)	C22—C231	1.392 (2)
C2—H2	0.9500	C24—C231	1.367 (3)
C3—C21	1.5190 (19)	C24—C251	1.373 (3)
C11—C12	1.3950 (19)	C24—H24	0.9500
C11—C16	1.402 (2)	C26—C251	1.389 (2)
C12—C13	1.384 (2)	C231—F231	1.321 (2)
C12—H12	0.9500	C251—H251	0.9500
C13—C14	1.368 (3)

C2—C1—C11	127.18 (13)	C16—C15—H15	120.7
C2—C1—H1	116.4	C15—C16—C11	120.76 (14)
C11—C1—H1	116.4	C15—C16—H16	119.6
C1—C2—C3	123.09 (13)	C11—C16—H16	119.6
C1—C2—H2	118.5	C26—C21—C22	117.71 (13)
C3—C2—H2	118.5	C26—C21—C3	121.98 (13)
O1—C3—C2	121.99 (13)	C22—C21—C3	120.31 (14)
O1—C3—C21	119.41 (13)	C21—C22—C231	120.61 (16)
C2—C3—C21	118.59 (11)	C21—C22—Cl2	120.04 (12)
C12—C11—C16	118.39 (13)	C231—C22—Cl2	119.35 (13)
C12—C11—C1	118.21 (13)	C231—C24—C251	119.29 (15)
C16—C11—C1	123.38 (13)	C231—C24—H24	120.4
C13—C12—C11	121.12 (14)	C251—C24—H24	120.4
C13—C12—H12	119.4	C21—C26—C251	121.18 (15)
C11—C12—H12	119.4	C21—C26—Cl1	120.02 (11)
C14—C13—C12	118.20 (15)	C251—C26—Cl1	118.79 (14)
C14—C13—H13	120.9	F231—C231—C24	119.34 (17)
C12—C13—H13	120.9	F231—C231—C22	119.7 (2)
F1—C14—C13	118.73 (16)	C24—C231—C22	120.88 (16)
F1—C14—C15	118.28 (16)	C24—C251—C26	120.32 (17)
C13—C14—C15	122.98 (15)	C24—C251—H251	119.8
C14—C15—C16	118.52 (15)	C26—C251—H251	119.8
C14—C15—H15	120.7

C11—C1—C2—C3	179.51 (13)	C2—C3—C21—C22	−94.75 (16)
C1—C2—C3—O1	180.00 (14)	C26—C21—C22—C231	−0.9 (2)
C1—C2—C3—C21	−1.2 (2)	C3—C21—C22—C231	179.49 (13)
C2—C1—C11—C12	172.16 (14)	C26—C21—C22—Cl2	179.08 (11)
C2—C1—C11—C16	−9.1 (2)	C3—C21—C22—Cl2	−0.51 (18)
C16—C11—C12—C13	1.1 (2)	C22—C21—C26—C251	0.7 (2)
C1—C11—C12—C13	179.87 (14)	C3—C21—C26—C251	−179.74 (13)
C11—C12—C13—C14	−1.4 (2)	C22—C21—C26—Cl1	−179.36 (11)
C12—C13—C14—F1	−178.78 (15)	C3—C21—C26—Cl1	0.22 (19)
C12—C13—C14—C15	0.7 (3)	C251—C24—C231—F231	177.32 (16)
F1—C14—C15—C16	179.77 (15)	C251—C24—C231—C22	0.3 (2)
C13—C14—C15—C16	0.3 (3)	C21—C22—C231—F231	−176.54 (16)
C14—C15—C16—C11	−0.6 (2)	Cl2—C22—C231—F231	3.5 (2)
C12—C11—C16—C15	−0.1 (2)	C21—C22—C231—C24	0.4 (2)
C1—C11—C16—C15	−178.78 (14)	Cl2—C22—C231—C24	−179.57 (13)
O1—C3—C21—C26	−95.46 (17)	C231—C24—C251—C26	−0.6 (2)
C2—C3—C21—C26	85.68 (17)	C21—C26—C251—C24	0.1 (2)
O1—C3—C21—C22	84.11 (18)	Cl1—C26—C251—C24	−179.89 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.95	2.51	3.3982 (16)	156
C12—H12···O1ⁱ	0.95	2.55	3.4266 (19)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.95	2.51	3.3982 (16)	156
C12—H12⋯O1ⁱ	0.95	2.55	3.4266 (19)	153

Symmetry code: (i) .

7 in total

Review 1. A review of anti-infective and anti-inflammatory chalcones.

Authors: Zdzisława Nowakowska
Journal: Eur J Med Chem Date: 2006-11-15 Impact factor: 6.514

2. Anticancer activities of novel chalcone and bis-chalcone derivatives.

Authors: Aneta Modzelewska; Catherine Pettit; Geetha Achanta; Nancy E Davidson; Peng Huang; Saeed R Khan
Journal: Bioorg Med Chem Date: 2006-01-24 Impact factor: 3.641

3. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

4. Graph-set analysis of hydrogen-bond patterns in organic crystals.

Authors: M C Etter; J C MacDonald; J Bernstein
Journal: Acta Crystallogr B Date: 1990-04-01

5. Antibacterial chalcones--bioisosteric replacement of the 4'-hydroxy group.

Authors: Simon Feldbaek Nielsen; Thomas Boesen; Mogens Larsen; Kristian Schønning; Hasse Kromann
Journal: Bioorg Med Chem Date: 2004-06-01 Impact factor: 3.641

6. (E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(4-methyl-phen-yl)prop-2-en-1-one.

Authors: Richard Betz; Thomas Gerber; Eric Hosten; Seranthimata Samshuddin; Badiadka Narayana; Hemmige S Yathirajan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-11-05

7. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20