Literature DB >> 23476217

(2E)-3-[4-(Benz-yloxy)phen-yl]-1-(2,6-dichloro-3-fluoro-phen-yl)prop-2-en-1-one.

Aletti S Praveen¹, Hemmige S Yathirajan, Thomas Gerber, Benjamin van Brecht, Richard Betz.

Abstract

In the title compound, C22H15Cl2FO2, a chalcone derivative featuring a threefold-halogenated aromatic substituent, the conformation about the C=C bond is E. In the crystal C-H⋯F and C-H⋯Cl contacts connect the mol-ecules into undulating sheets parallel to (101). In addition, C-H⋯π inter-actions are also present.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 23476217 PMCID： PMC3588981 DOI： 10.1107/S1600536812046855

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

Related literature

For background to possible applications of chalcones in pharmacy and industry, see: Lin et al. (2002 ▶); Modzelewska et al. (2006 ▶); Svetaz et al. (2004 ▶); Sarojini et al. (2006 ▶). For related structures, see: Yathirajan et al. (2006 ▶); Betz et al. (2012 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H15Cl2FO2 M = 401.24 Monoclinic, a = 9.1977 (2) Å b = 21.6887 (4) Å c = 11.6072 (2) Å β = 124.629 (1)° V = 1905.29 (6) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 200 K 0.40 × 0.17 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.681, T max = 0.746 17237 measured reflections 4712 independent reflections 3729 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.101 S = 1.02 4712 reflections 244 parameters H-atom parameters constrained Δρmax = 0.40 e Å−3 Δρmin = −0.27 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046855/nc2298sup1.cif Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812046855/nc2298Isup2.cdx Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046855/nc2298Isup3.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812046855/nc2298Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₂H₁₅Cl₂FO₂	F(000) = 824
M_r = 401.24	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 369–367 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.1977 (2) Å	Cell parameters from 8954 reflections
b = 21.6887 (4) Å	θ = 2.5–28.3°
c = 11.6072 (2) Å	µ = 0.36 mm⁻¹
β = 124.629 (1)°	T = 200 K
V = 1905.29 (6) Å³	Cube, white
Z = 4	0.40 × 0.17 × 0.14 mm

Bruker APEXII CCD diffractometer	4712 independent reflections
Radiation source: fine-focus sealed tube	3729 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
T_min = 0.681, T_max = 0.746	k = −20→28
17237 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.041P)² + 0.8279P] where P = (F_o² + 2F_c²)/3
4712 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

	x	y	z	U_iso*/U_eq
Cl1	1.07669 (6)	0.33062 (2)	0.86095 (4)	0.05144 (14)
Cl2	1.60001 (7)	0.17443 (2)	1.21644 (5)	0.05090 (14)
F1	1.35724 (19)	0.38832 (5)	0.85238 (13)	0.0634 (3)
O1	1.20670 (18)	0.23629 (6)	1.15009 (13)	0.0490 (3)
O2	0.66727 (17)	−0.00811 (5)	0.41450 (12)	0.0422 (3)
C1	1.2218 (2)	0.22034 (7)	1.05687 (16)	0.0338 (3)
C2	1.1208 (2)	0.16972 (8)	0.96163 (17)	0.0384 (4)
H2	1.0530	0.1445	0.9813	0.046*
C3	1.1186 (2)	0.15692 (7)	0.84785 (16)	0.0319 (3)
H3	1.1970	0.1800	0.8360	0.038*
C4	0.6360 (2)	−0.00076 (8)	0.27948 (17)	0.0397 (4)
H4A	0.7452	−0.0099	0.2848	0.048*
H4B	0.6001	0.0422	0.2465	0.048*
C11	1.3486 (2)	0.25530 (6)	1.03696 (14)	0.0283 (3)
C12	1.2938 (2)	0.30701 (7)	0.95115 (15)	0.0323 (3)
C13	1.4134 (3)	0.33938 (7)	0.93831 (17)	0.0394 (4)
C14	1.5873 (3)	0.32290 (8)	1.01107 (18)	0.0421 (4)
H14	1.6678	0.3463	1.0022	0.050*
C15	1.6452 (2)	0.27204 (8)	1.09749 (17)	0.0393 (4)
H15	1.7658	0.2601	1.1489	0.047*
C16	1.5253 (2)	0.23868 (7)	1.10837 (15)	0.0316 (3)
C21	1.0085 (2)	0.11127 (7)	0.73997 (16)	0.0316 (3)
C22	0.8987 (2)	0.06930 (8)	0.74900 (17)	0.0397 (4)
H22	0.9000	0.0682	0.8314	0.048*
C23	0.7894 (3)	0.02991 (8)	0.64018 (18)	0.0423 (4)
H23	0.7164	0.0018	0.6482	0.051*
C24	0.7851 (2)	0.03105 (7)	0.51816 (16)	0.0343 (3)
C25	0.8940 (2)	0.07133 (7)	0.50716 (17)	0.0340 (3)
H25	0.8936	0.0719	0.4252	0.041*
C26	1.0036 (2)	0.11089 (7)	0.61807 (17)	0.0338 (3)
H26	1.0775	0.1386	0.6102	0.041*
C31	0.4920 (2)	−0.04454 (7)	0.18024 (16)	0.0351 (3)
C32	0.5074 (2)	−0.10705 (8)	0.21101 (17)	0.0392 (4)
H32	0.6079	−0.1217	0.2969	0.047*
C33	0.3791 (3)	−0.14809 (9)	0.11877 (18)	0.0459 (4)
H33	0.3918	−0.1907	0.1414	0.055*
C34	0.2328 (3)	−0.12764 (10)	−0.00587 (19)	0.0499 (5)
H34	0.1447	−0.1561	−0.0695	0.060*
C35	0.2144 (3)	−0.06611 (11)	−0.03803 (19)	0.0570 (5)
H35	0.1131	−0.0519	−0.1240	0.068*
C36	0.3439 (3)	−0.02427 (9)	0.05494 (19)	0.0489 (4)
H36	0.3302	0.0183	0.0321	0.059*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0470 (3)	0.0639 (3)	0.0343 (2)	0.0235 (2)	0.01765 (19)	0.00794 (19)
Cl2	0.0530 (3)	0.0481 (3)	0.0527 (3)	0.0169 (2)	0.0307 (2)	0.0229 (2)
F1	0.0982 (10)	0.0362 (6)	0.0626 (7)	0.0085 (6)	0.0497 (7)	0.0160 (5)
O1	0.0587 (8)	0.0596 (8)	0.0430 (7)	−0.0113 (7)	0.0375 (7)	−0.0124 (6)
O2	0.0528 (7)	0.0349 (6)	0.0353 (6)	−0.0162 (5)	0.0228 (6)	−0.0089 (5)
C1	0.0340 (8)	0.0385 (8)	0.0293 (7)	−0.0024 (7)	0.0183 (6)	−0.0012 (6)
C2	0.0388 (9)	0.0404 (9)	0.0404 (8)	−0.0120 (7)	0.0251 (7)	−0.0061 (7)
C3	0.0299 (8)	0.0297 (7)	0.0336 (7)	−0.0026 (6)	0.0166 (6)	−0.0014 (6)
C4	0.0460 (9)	0.0328 (8)	0.0352 (8)	−0.0060 (7)	0.0200 (7)	−0.0020 (7)
C11	0.0337 (8)	0.0275 (7)	0.0219 (6)	−0.0026 (6)	0.0147 (6)	−0.0044 (5)
C12	0.0373 (8)	0.0321 (7)	0.0233 (7)	0.0029 (6)	0.0147 (6)	−0.0032 (6)
C13	0.0610 (11)	0.0252 (7)	0.0335 (8)	−0.0018 (7)	0.0277 (8)	0.0006 (6)
C14	0.0498 (10)	0.0384 (9)	0.0427 (9)	−0.0165 (8)	0.0291 (8)	−0.0073 (7)
C15	0.0339 (8)	0.0436 (9)	0.0362 (8)	−0.0060 (7)	0.0174 (7)	−0.0049 (7)
C16	0.0355 (8)	0.0292 (7)	0.0271 (7)	0.0012 (6)	0.0160 (6)	0.0017 (6)
C21	0.0304 (7)	0.0271 (7)	0.0334 (7)	−0.0014 (6)	0.0157 (6)	−0.0019 (6)
C22	0.0506 (10)	0.0338 (8)	0.0338 (8)	−0.0099 (7)	0.0235 (8)	−0.0017 (6)
C23	0.0532 (11)	0.0325 (8)	0.0405 (9)	−0.0151 (8)	0.0261 (8)	−0.0026 (7)
C24	0.0385 (9)	0.0235 (7)	0.0355 (8)	−0.0037 (6)	0.0178 (7)	−0.0043 (6)
C25	0.0351 (8)	0.0325 (8)	0.0365 (8)	−0.0018 (7)	0.0216 (7)	−0.0052 (6)
C26	0.0323 (8)	0.0316 (8)	0.0401 (8)	−0.0043 (6)	0.0221 (7)	−0.0051 (6)
C31	0.0375 (8)	0.0357 (8)	0.0298 (7)	−0.0025 (7)	0.0178 (7)	−0.0019 (6)
C32	0.0424 (9)	0.0380 (9)	0.0296 (8)	−0.0038 (7)	0.0160 (7)	0.0003 (6)
C33	0.0602 (12)	0.0400 (9)	0.0399 (9)	−0.0137 (9)	0.0299 (9)	−0.0075 (7)
C34	0.0494 (11)	0.0637 (12)	0.0352 (9)	−0.0186 (10)	0.0232 (8)	−0.0167 (8)
C35	0.0410 (10)	0.0772 (15)	0.0328 (9)	0.0045 (10)	0.0091 (8)	−0.0019 (9)
C36	0.0474 (11)	0.0455 (10)	0.0409 (9)	0.0067 (8)	0.0175 (8)	0.0052 (8)

Cl1—C12	1.7230 (17)	C15—H15	0.9500
Cl2—C16	1.7344 (15)	C21—C26	1.389 (2)
F1—C13	1.3425 (18)	C21—C22	1.408 (2)
O1—C1	1.2167 (19)	C22—C23	1.376 (2)
O2—C24	1.3643 (18)	C22—H22	0.9500
O2—C4	1.4327 (19)	C23—C24	1.395 (2)
C1—C2	1.457 (2)	C23—H23	0.9500
C1—C11	1.515 (2)	C24—C25	1.388 (2)
C2—C3	1.338 (2)	C25—C26	1.391 (2)
C2—H2	0.9500	C25—H25	0.9500
C3—C21	1.460 (2)	C26—H26	0.9500
C3—H3	0.9500	C31—C36	1.383 (2)
C4—C31	1.500 (2)	C31—C32	1.389 (2)
C4—H4A	0.9900	C32—C33	1.377 (2)
C4—H4B	0.9900	C32—H32	0.9500
C11—C16	1.388 (2)	C33—C34	1.374 (3)
C11—C12	1.390 (2)	C33—H33	0.9500
C12—C13	1.383 (2)	C34—C35	1.370 (3)
C13—C14	1.366 (3)	C34—H34	0.9500
C14—C15	1.378 (2)	C35—C36	1.395 (3)
C14—H14	0.9500	C35—H35	0.9500
C15—C16	1.383 (2)	C36—H36	0.9500

C24—O2—C4	117.41 (12)	C26—C21—C3	118.88 (14)
O1—C1—C2	122.91 (15)	C22—C21—C3	123.48 (14)
O1—C1—C11	118.69 (14)	C23—C22—C21	120.93 (15)
C2—C1—C11	118.39 (13)	C23—C22—H22	119.5
C3—C2—C1	123.41 (15)	C21—C22—H22	119.5
C3—C2—H2	118.3	C22—C23—C24	120.38 (15)
C1—C2—H2	118.3	C22—C23—H23	119.8
C2—C3—C21	126.97 (15)	C24—C23—H23	119.8
C2—C3—H3	116.5	O2—C24—C25	124.31 (14)
C21—C3—H3	116.5	O2—C24—C23	115.75 (14)
O2—C4—C31	108.06 (13)	C25—C24—C23	119.92 (14)
O2—C4—H4A	110.1	C24—C25—C26	118.97 (14)
C31—C4—H4A	110.1	C24—C25—H25	120.5
O2—C4—H4B	110.1	C26—C25—H25	120.5
C31—C4—H4B	110.1	C21—C26—C25	122.23 (15)
H4A—C4—H4B	108.4	C21—C26—H26	118.9
C16—C11—C12	117.55 (14)	C25—C26—H26	118.9
C16—C11—C1	121.37 (13)	C36—C31—C32	118.46 (16)
C12—C11—C1	121.01 (14)	C36—C31—C4	121.24 (16)
C13—C12—C11	119.96 (15)	C32—C31—C4	120.27 (15)
C13—C12—Cl1	120.13 (12)	C33—C32—C31	120.94 (16)
C11—C12—Cl1	119.91 (13)	C33—C32—H32	119.5
F1—C13—C14	119.16 (16)	C31—C32—H32	119.5
F1—C13—C12	119.19 (17)	C34—C33—C32	120.26 (18)
C14—C13—C12	121.65 (15)	C34—C33—H33	119.9
C13—C14—C15	119.46 (16)	C32—C33—H33	119.9
C13—C14—H14	120.3	C35—C34—C33	119.79 (17)
C15—C14—H14	120.3	C35—C34—H34	120.1
C14—C15—C16	119.14 (16)	C33—C34—H34	120.1
C14—C15—H15	120.4	C34—C35—C36	120.27 (18)
C16—C15—H15	120.4	C34—C35—H35	119.9
C15—C16—C11	122.21 (14)	C36—C35—H35	119.9
C15—C16—Cl2	118.54 (13)	C31—C36—C35	120.29 (18)
C11—C16—Cl2	119.25 (12)	C31—C36—H36	119.9
C26—C21—C22	117.55 (14)	C35—C36—H36	119.9

O1—C1—C2—C3	170.87 (17)	C2—C3—C21—C26	169.97 (17)
C11—C1—C2—C3	−8.0 (2)	C2—C3—C21—C22	−6.4 (3)
C1—C2—C3—C21	−173.56 (16)	C26—C21—C22—C23	−0.6 (3)
C24—O2—C4—C31	−175.17 (14)	C3—C21—C22—C23	175.83 (16)
O1—C1—C11—C16	88.4 (2)	C21—C22—C23—C24	−0.2 (3)
C2—C1—C11—C16	−92.69 (18)	C4—O2—C24—C25	−9.4 (2)
O1—C1—C11—C12	−88.61 (19)	C4—O2—C24—C23	169.19 (15)
C2—C1—C11—C12	90.29 (18)	C22—C23—C24—O2	−177.49 (16)
C16—C11—C12—C13	0.7 (2)	C22—C23—C24—C25	1.2 (3)
C1—C11—C12—C13	177.82 (13)	O2—C24—C25—C26	177.34 (15)
C16—C11—C12—Cl1	−179.34 (11)	C23—C24—C25—C26	−1.2 (2)
C1—C11—C12—Cl1	−2.20 (19)	C22—C21—C26—C25	0.6 (2)
C11—C12—C13—F1	178.39 (13)	C3—C21—C26—C25	−176.04 (15)
Cl1—C12—C13—F1	−1.6 (2)	C24—C25—C26—C21	0.3 (2)
C11—C12—C13—C14	−1.7 (2)	O2—C4—C31—C36	127.10 (17)
Cl1—C12—C13—C14	178.27 (13)	O2—C4—C31—C32	−54.7 (2)
F1—C13—C14—C15	−178.82 (15)	C36—C31—C32—C33	0.4 (3)
C12—C13—C14—C15	1.3 (3)	C4—C31—C32—C33	−177.76 (16)
C13—C14—C15—C16	0.1 (2)	C31—C32—C33—C34	−0.1 (3)
C14—C15—C16—C11	−1.2 (2)	C32—C33—C34—C35	−0.3 (3)
C14—C15—C16—Cl2	179.46 (12)	C33—C34—C35—C36	0.3 (3)
C12—C11—C16—C15	0.8 (2)	C32—C31—C36—C35	−0.4 (3)
C1—C11—C16—C15	−176.37 (14)	C4—C31—C36—C35	177.73 (18)
C12—C11—C16—Cl2	−179.88 (11)	C34—C35—C36—C31	0.1 (3)
C1—C11—C16—Cl2	2.99 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···F1ⁱ	0.95	2.55	3.375 (2)	145
C34—H34···Cl1ⁱⁱ	0.95	2.80	3.5462 (18)	136
C14—H14···Cgⁱⁱⁱ	0.95	2.51	3.297 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯F1ⁱ	0.95	2.55	3.375 (2)	145
C34—H34⋯Cl1ⁱⁱ	0.95	2.80	3.5462 (18)	136
C14—H14⋯Cg ⁱⁱⁱ	0.95	2.51	3.297 (2)	140

Symmetry codes: (i) ; (ii) ; (iii) .

7 in total

(2E)-3-[4-(Benz-yloxy)phen-yl]-1-(2,6-dichloro-3-fluoro-phen-yl)prop-2-en-1-one.

Related literature

Experimental

Crystal data

Data collection

Refinement

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