Literature DB >> 21754055

(1E,4E)-1,5-Bis(2,6-difluoro-phen-yl)penta-1,4-dien-3-one.

Jun-Da Huang, Qin-Qin Tang, Xiao-Yan Chen, Yun Ye, Yi Wang.

Abstract

The mol-ecule of the title compound, C(17)H(10)F(4)O, is roughly planar, with a dihedral angle of 5.59 (14)° between the two phenyl rings. The mol-ecule has an E conformation with respect to the olefinic bonds. In the crystal, mol-ecules are connected through C-H⋯O hydrogen bonds and there is slipped π-π stacking [centroid-centroid distance = 3.7983 (18), slippage =1.309 ;Å] between symmetry-related benzene rings.

Entities: Chemical Disease Gene Species

Year: 2011 PMID： 21754055 PMCID： PMC3099841 DOI： 10.1107/S1600536811007070

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

Related literature

The title compound is a derivative of the biologically active compound curcumin [systematic name (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione]. For the biological activity and applications of curcumin, see: Aggarwal et al. (2007 ▶); Kamat et al. (2009 ▶); Liang et al. (2009 ▶); Pan et al. (1999 ▶); Sharma et al. (2007 ▶); Zhao et al. (2010a ▶,b ▶). For related structures, see: Zhao et al. (2009 ▶); Liang et al. (2007 ▶).

Experimental

Crystal data

C17H10F4O M = 306.25 Monoclinic, a = 7.7522 (11) Å b = 15.413 (2) Å c = 12.2848 (17) Å β = 106.194 (2)° V = 1409.6 (3) Å3 Z = 4 Mo Kα radiation μ = 0.13 mm−1 T = 293 K 0.40 × 0.37 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.640, T max = 1.000 7288 measured reflections 2622 independent reflections 1612 reflections with I > 2σ(I) R int = 0.111

Refinement

R[F 2 > 2σ(F 2)] = 0.063 wR(F 2) = 0.174 S = 0.94 2622 reflections 199 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.24 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007070/dn2659sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007070/dn2659Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₀F₄O	F(000) = 624
M_r = 306.25	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1937 reflections
a = 7.7522 (11) Å	θ = 5.3–44.2°
b = 15.413 (2) Å	µ = 0.13 mm⁻¹
c = 12.2848 (17) Å	T = 293 K
β = 106.194 (2)°	Prismatic, green
V = 1409.6 (3) Å³	0.40 × 0.37 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2622 independent reflections
Radiation source: fine-focus sealed tube	1612 reflections with I > 2σ(I)
graphite	R_int = 0.111
φ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
T_min = 0.640, T_max = 1.000	k = −10→18
7288 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0971P)²] where P = (F_o² + 2F_c²)/3
2622 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	U_iso*/U_eq
F1	0.1321 (2)	−0.05696 (10)	−0.13761 (11)	0.0953 (6)
F2	0.2040 (3)	−0.14772 (13)	0.23505 (14)	0.1253 (7)
F3	0.4725 (3)	0.31282 (12)	−0.12340 (13)	0.1193 (7)
F4	0.7788 (3)	0.37861 (11)	0.25107 (15)	0.1277 (7)
O1	0.4636 (3)	0.11929 (12)	0.21918 (15)	0.0902 (6)
C1	0.4216 (3)	0.12103 (15)	0.1155 (2)	0.0650 (6)
C2	0.3222 (3)	0.04845 (15)	0.0490 (2)	0.0651 (6)
H2	0.2925	0.0506	−0.0297	0.078*
C3	0.2739 (3)	−0.01982 (16)	0.09889 (19)	0.0665 (6)
H3	0.3101	−0.0180	0.1777	0.080*
C4	0.1752 (3)	−0.09625 (15)	0.05189 (18)	0.0625 (6)
C5	0.1051 (3)	−0.11493 (15)	−0.06245 (19)	0.0654 (6)
C6	0.0106 (3)	−0.18811 (17)	−0.1029 (2)	0.0761 (7)
H6	−0.0336	−0.1970	−0.1806	0.091*
C7	−0.0187 (4)	−0.24790 (18)	−0.0290 (3)	0.0816 (8)
H7	−0.0837	−0.2979	−0.0561	0.098*
C8	0.0473 (4)	−0.23481 (19)	0.0854 (3)	0.0908 (8)
H8	0.0285	−0.2755	0.1368	0.109*
C9	0.1404 (4)	−0.16122 (19)	0.1214 (2)	0.0793 (7)
C10	0.4659 (3)	0.19589 (16)	0.0545 (2)	0.0672 (6)
H10	0.4252	0.1973	−0.0242	0.081*
C11	0.5625 (3)	0.26144 (16)	0.10904 (19)	0.0657 (6)
H11	0.5979	0.2561	0.1876	0.079*
C12	0.6217 (3)	0.33956 (16)	0.06650 (19)	0.0652 (6)
C13	0.5821 (3)	0.36416 (17)	−0.0465 (2)	0.0776 (7)
C14	0.6445 (4)	0.4382 (2)	−0.0837 (3)	0.0964 (9)
H14	0.6124	0.4518	−0.1605	0.116*
C15	0.7535 (4)	0.4915 (2)	−0.0071 (3)	0.0980 (9)
H15	0.7977	0.5417	−0.0316	0.118*
C16	0.7993 (4)	0.4721 (2)	0.1059 (3)	0.1009 (9)
H16	0.8741	0.5086	0.1588	0.121*
C17	0.7330 (3)	0.39840 (19)	0.1388 (2)	0.0832 (7)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1352 (13)	0.0939 (11)	0.0506 (8)	−0.0214 (9)	0.0155 (8)	0.0034 (7)
F2	0.1765 (17)	0.1274 (15)	0.0600 (10)	−0.0324 (12)	0.0129 (10)	0.0212 (9)
F3	0.1636 (15)	0.1215 (14)	0.0553 (9)	−0.0532 (12)	0.0018 (10)	0.0006 (9)
F4	0.1733 (17)	0.1124 (14)	0.0678 (11)	−0.0292 (12)	−0.0153 (10)	−0.0118 (10)
O1	0.1242 (15)	0.0820 (13)	0.0543 (11)	−0.0036 (10)	0.0084 (10)	−0.0012 (8)
C1	0.0676 (14)	0.0680 (15)	0.0553 (14)	0.0125 (11)	0.0102 (11)	−0.0008 (11)
C2	0.0719 (14)	0.0696 (15)	0.0512 (13)	0.0085 (11)	0.0131 (11)	−0.0007 (11)
C3	0.0693 (14)	0.0775 (17)	0.0506 (13)	0.0115 (12)	0.0134 (11)	0.0023 (12)
C4	0.0636 (13)	0.0656 (14)	0.0564 (14)	0.0099 (11)	0.0138 (10)	0.0024 (11)
C5	0.0739 (14)	0.0653 (15)	0.0564 (14)	0.0119 (12)	0.0175 (11)	0.0070 (11)
C6	0.0829 (16)	0.0755 (17)	0.0668 (16)	0.0058 (14)	0.0154 (13)	−0.0075 (13)
C7	0.0841 (17)	0.0689 (17)	0.093 (2)	0.0029 (13)	0.0272 (16)	−0.0040 (15)
C8	0.107 (2)	0.0768 (19)	0.093 (2)	0.0019 (16)	0.0336 (18)	0.0170 (16)
C9	0.0933 (18)	0.0828 (19)	0.0561 (15)	0.0050 (15)	0.0114 (13)	0.0086 (13)
C10	0.0671 (14)	0.0771 (17)	0.0525 (13)	0.0059 (12)	0.0088 (11)	−0.0050 (12)
C11	0.0675 (13)	0.0731 (16)	0.0518 (13)	0.0063 (12)	0.0087 (11)	−0.0052 (11)
C12	0.0629 (13)	0.0707 (16)	0.0588 (14)	0.0052 (11)	0.0118 (11)	−0.0061 (11)
C13	0.0811 (16)	0.0853 (18)	0.0611 (15)	−0.0131 (14)	0.0109 (12)	−0.0040 (13)
C14	0.111 (2)	0.096 (2)	0.0788 (19)	−0.0156 (18)	0.0214 (17)	0.0115 (16)
C15	0.099 (2)	0.082 (2)	0.112 (3)	−0.0120 (16)	0.0258 (19)	0.0076 (18)
C16	0.094 (2)	0.081 (2)	0.112 (3)	−0.0177 (17)	0.0032 (18)	−0.0135 (18)
C17	0.0870 (17)	0.0844 (19)	0.0655 (17)	−0.0005 (15)	0.0004 (13)	−0.0089 (14)

F1—C5	1.342 (3)	C7—H7	0.9300
F2—C9	1.361 (3)	C8—C9	1.351 (4)
F3—C13	1.339 (3)	C8—H8	0.9300
F4—C17	1.360 (3)	C10—C11	1.323 (3)
O1—C1	1.224 (3)	C10—H10	0.9300
C1—C10	1.468 (3)	C11—C12	1.438 (3)
C1—C2	1.470 (3)	C11—H11	0.9300
C2—C3	1.323 (3)	C12—C13	1.388 (3)
C2—H2	0.9300	C12—C17	1.389 (3)
C3—C4	1.436 (3)	C13—C14	1.367 (4)
C3—H3	0.9300	C14—C15	1.353 (4)
C4—C5	1.388 (3)	C14—H14	0.9300
C4—C9	1.390 (4)	C15—C16	1.367 (4)
C5—C6	1.361 (3)	C15—H15	0.9300
C6—C7	1.357 (4)	C16—C17	1.354 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.370 (4)

O1—C1—C10	121.1 (2)	F2—C9—C4	116.3 (2)
O1—C1—C2	120.5 (2)	C11—C10—C1	121.5 (2)
C10—C1—C2	118.4 (2)	C11—C10—H10	119.3
C3—C2—C1	121.3 (2)	C1—C10—H10	119.3
C3—C2—H2	119.3	C10—C11—C12	130.4 (2)
C1—C2—H2	119.3	C10—C11—H11	114.8
C2—C3—C4	130.9 (2)	C12—C11—H11	114.8
C2—C3—H3	114.6	C13—C12—C17	112.7 (2)
C4—C3—H3	114.6	C13—C12—C11	126.0 (2)
C5—C4—C9	112.6 (2)	C17—C12—C11	121.2 (2)
C5—C4—C3	126.3 (2)	F3—C13—C14	118.1 (2)
C9—C4—C3	121.1 (2)	F3—C13—C12	117.6 (2)
F1—C5—C6	118.1 (2)	C14—C13—C12	124.2 (3)
F1—C5—C4	117.8 (2)	C15—C14—C13	119.0 (3)
C6—C5—C4	124.1 (2)	C15—C14—H14	120.5
C7—C6—C5	119.4 (3)	C13—C14—H14	120.5
C7—C6—H6	120.3	C14—C15—C16	120.6 (3)
C5—C6—H6	120.3	C14—C15—H15	119.7
C6—C7—C8	120.2 (3)	C16—C15—H15	119.7
C6—C7—H7	119.9	C17—C16—C15	118.3 (3)
C8—C7—H7	119.9	C17—C16—H16	120.9
C9—C8—C7	118.2 (3)	C15—C16—H16	120.9
C9—C8—H8	120.9	C16—C17—F4	118.5 (3)
C7—C8—H8	120.9	C16—C17—C12	125.2 (3)
C8—C9—F2	118.1 (2)	F4—C17—C12	116.2 (3)
C8—C9—C4	125.5 (3)

O1—C1—C2—C3	0.7 (3)	O1—C1—C10—C11	4.4 (3)
C10—C1—C2—C3	−178.2 (2)	C2—C1—C10—C11	−176.71 (19)
C1—C2—C3—C4	178.8 (2)	C1—C10—C11—C12	179.4 (2)
C2—C3—C4—C5	−0.4 (4)	C10—C11—C12—C13	2.2 (4)
C2—C3—C4—C9	179.5 (2)	C10—C11—C12—C17	−175.9 (2)
C9—C4—C5—F1	−179.4 (2)	C17—C12—C13—F3	−178.6 (2)
C3—C4—C5—F1	0.5 (3)	C11—C12—C13—F3	3.1 (4)
C9—C4—C5—C6	0.8 (3)	C17—C12—C13—C14	−0.2 (4)
C3—C4—C5—C6	−179.3 (2)	C11—C12—C13—C14	−178.5 (2)
F1—C5—C6—C7	179.9 (2)	F3—C13—C14—C15	179.2 (3)
C4—C5—C6—C7	−0.2 (4)	C12—C13—C14—C15	0.8 (5)
C5—C6—C7—C8	−0.3 (4)	C13—C14—C15—C16	−0.7 (5)
C6—C7—C8—C9	0.3 (4)	C14—C15—C16—C17	0.1 (5)
C7—C8—C9—F2	179.2 (2)	C15—C16—C17—F4	179.7 (3)
C7—C8—C9—C4	0.4 (4)	C15—C16—C17—C12	0.5 (5)
C5—C4—C9—C8	−0.9 (4)	C13—C12—C17—C16	−0.4 (4)
C3—C4—C9—C8	179.2 (2)	C11—C12—C17—C16	177.9 (3)
C5—C4—C9—F2	−179.7 (2)	C13—C12—C17—F4	−179.6 (2)
C3—C4—C9—F2	0.4 (3)	C11—C12—C17—F4	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.93	2.38	3.307 (4)	171
C8—H8···O1ⁱⁱ	0.93	2.39	3.308 (3)	170

CgI	CgJ	CgI···CgJ^a	CgI···P(J)^b	CgJ···P(I)^c	Slippage
Cg1	Cg1ⁱⁱⁱ	3.7983 (18)	3.5656 (12)	3.5656 (12)	1.309

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1ⁱ	0.93	2.38	3.307 (4)	171
C8—H8⋯O1ⁱⁱ	0.93	2.39	3.308 (3)	170

Symmetry codes: (i) ; (ii) .

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