(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluoro­phen­yl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis

Amzar Ahlami Abdullah; Nur Hafiq Hanif Hassan; Suhana Arshad; Nuridayanti Che Khalib; Ibrahim Abdul Razak

doi:10.1107/S2056989016005028

. 2016 Apr 8;72(Pt 5):648–651. doi: 10.1107/S2056989016005028

(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis

Amzar Ahlami Abdullah ^a, Nur Hafiq Hanif Hassan ^a, Suhana Arshad ^a,^‡, Nuridayanti Che Khalib ^a, Ibrahim Abdul Razak ^a,^*,^§

PMCID: PMC4908534 PMID: 27308010

In the title compund, the enone moiety adopts an E conformation. An intramolecular C—H⋯F hydrogen bond generates an S(6) ring motif. In the crystal, molecules are arranged into centrosymmetric dimers via pairs of C—H⋯F hydrogen bonds. The crystal structure also features C—H⋯π and π–π interactions. Hirshfeld surface analysis was used to confirm the existence of intermolecular interactions.

Keywords: crystal structure, chalcone, hydrogen bonding, Hirshfeld surface analysis

Abstract

In the title compound, C₂₃H₁₄ClFO, the enone moiety adopts an E conformation. The dihedral angle between the benzene and anthracene ring is 63.42 (8)° and an intramolecular C—H⋯F hydrogen bond generates an S(6) ring motif. In the crystal, molecules are arranged into centrosymmetric dimers via pairs of C—H⋯F hydrogen bonds. The crystal structure also features C—H⋯π and π–π interactions. Hirshfeld surface analysis was used to confirm the existence of intermolecular interactions.

Chemical context

The biological properties of chalcone derivatives such as anticancer (Bhat et al., 2005 ▸), antimalarial (Xue et al., 2004 ▸), anti-oxidant and antimicrobial (Yayli et al., 2006 ▸), antiplatelet (Zhao et al., 2005 ▸) as well as anti-inflammatory (Madan et al., 2000 ▸) have been studied extensively and developed. As part of our own studies in this area, we hereby report the synthesis and crystal structure of the title compound.

Structural commentary

The molecular structure of the title chalcone is shown in Fig. 1 ▸. The enone moiety (O1/C7–C9) adopts an E conformation with respect to the C7=C8 bond. The anthracene ring system (C10–C23) is twisted at the C9–C10 bond from the (E)-3-(2-chloro-6-fluorophenyl)acrylaldehyde moiety [maximum deviation = 0.193 (16) Å for atom O1] with a C8—C9—C10—C23 torsion angle of −61.4 (2)°. The terminal benzene and anthracene ring systems (C1–C6 and C10–C23, respectively) form a dihedral angle of 63.42 (8)°. The least-squares plane through the enone moiety [O1/C7–C9) with a maximum deviation of 0.033 (2) Å for atom C9] makes dihedral angles of 5.62 (13) and 59.18 (12)° with the benzene (C1–C6) and anthracene (C10–C23) rings, respectively. An intramolecular C8—H8A⋯F1 hydrogen bond is observed, generating an S(6) ring motif. The bond lengths and angles are comparable with those in previously reported structures (Razak et al., 2009 ▸; Ngaini et al., 2011 ▸).

The molecular structure of the title compound, showing 50% probability displacement ellipsoids. The intramolecular C—H⋯F hydrogen bond is shown as a dashed line.

Supramolecular features

In the crystal (Fig. 2 ▸), the molecules are arranged into centrosymmetric dimers via pairs of C17—H17A⋯F1 (Table 1 ▸) hydrogen bonds. The crystal structure also features C14—H14A⋯Cg1 (Fig. 3 ▸) and Cg1⋯Cg1(1 − x, −y, 1 − z) interactions [centroid-to-centroid distance = 3.7557 (13) Å; Cg1 is the centroid of the C1–C6 ring].

The crystal packing showing the molecules arranged into centrosymmetric dimers. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯F1	0.93	2.19	2.808 (2)	123
C17—H17A⋯F1ⁱ	0.93	2.46	3.353 (2)	161
C14—H14A⋯Cg1ⁱⁱ	0.93	2.99	3.712 (3)	136

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Symmetry codes: (i) Inline graphic ; (ii) .

Detail of the crystal structure showing the C14—H14A⋯Cg1 interaction where Cg1 is the centroid of C1–C6 ring.

Hirshfeld surfaces analysis

The intermolecular interactions of the title compound can be visualized using Hirshfeld surface analysis (Wolff et al., 2012 ▸). The Hirshfeld surfaces mapped over d _norm are shown in Fig. 4 ▸. The 2-D fingerprint plots showing the occurrence of different kinds of intermolecular contacts are shown in Fig. 5 ▸.

d _norm mapped on the Hirshfeld surface for visualizing the intermolecular interactions of the title chalcone compound. Dotted lines (green) represent hydrogen bonds.

The 2-Dimensional fingerprint plot for the title chalcone compound showing contributions from different contacts.

The C17—H17A⋯F1 interactions are shown on the Hirshfeld surfaces marked with a bright-red spot for short contacts·The H⋯F/F⋯H contacts comprise 6.3% of the total Hirshfeld surface, represented by two symmetrical narrow pointed spikes with d_e + d_i ∼2.3 Å, suggesting the presence of a non-classical C—H⋯F hydrogen bond. The H⋯H contacts are shown on the fingerprint plot as one distinct spike with the minimum value of d_e + d_i. These contacts represent the largest contribution within the Hirshfeld surfaces (38.8%).

Significant C—H⋯π interactions (22.8%) can be also be seen, indicated by the wings of d_e + d_i ∼2.6 Å on the fingerprint plot. The presence of π–π interactions is shown as C⋯C contacts, which contribute 8.9% of the Hirshfeld surfaces. The presence of these interactions can also be shown by the Hirshfeld surfaces mapped by shape index (Fig. 6 ▸) and the Hirshfeld surfaces mapped with curvedness (Fig. 7 ▸).

Hirshfeld surface mapped over the shape index of the chalcone compound in (a) front view and (b) back view.

Hirshfeld surface mapped over curvedness of the chalcone compound in (a) front view and (b) back view.

Synthesis and crystallization

A mixture of 9-acetylanthracene (0.1 mol, 0.11 g) and 2-chloro-6-fluorobenzaldehyde (0.1 mol, 0.08 g) was dissolved in methanol (20 ml). A catalytic amount of NaOH (5 ml, 20%) was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 5–6 h at room temperature. After stirring, the contents of the flask were poured into ice-cold water (50 ml) and the resulting crude solid was collected by filtration. The compound was dried and purified by repeated recrystallization from acetone solution, forming yellow plates.

Refinement details

Crystal data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were positioned geometrically (C—H = 0.93 Å) and refined using a riding model with U _iso(H) = 1.2U _eq(C). The most disagreeable reflections (−1 − 2 4 and −1 1 0) were omitted from the final refinement.

Table 2. Experimental details.

Crystal data
Chemical formula	C₂₃H₁₄ClFO
M _r	360.79
Crystal system, space group	Triclinic, P
Temperature (K)	296
a, b, c (Å)	9.2846 (9), 9.8777 (10), 10.3624 (11)
α, β, γ (°)	94.364 (2), 113.3517 (19), 92.866 (2)
V (Å³)	866.63 (15)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.43 × 0.39 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 ▸)
T _min, T _max	0.905, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	15408, 3917, 2973
R _int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.046, 0.159, 1.04
No. of reflections	3917
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.38

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Computer programs: APEX2 and SAINT (Bruker, 2009 ▸), SHELXTL (Sheldrick, 2008 ▸) and SHELXL2014 (Sheldrick, 2015 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016005028/hb7569sup1.cif

e-72-00648-sup1.cif^{(618.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016005028/hb7569Isup2.hkl

e-72-00648-Isup2.hkl^{(214.9KB, hkl)}

Click here for additional data file.^{(6.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989016005028/hb7569Isup3.cml

CCDC reference: 1470351

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and Research University Grant No.1001/PFIZIK/811238 to conduct this work. NCK thanks the Malaysian Government for a MyBrain15 (MyPhD) scholarship

supplementary crystallographic information

Crystal data

C₂₃H₁₄ClFO	Z = 2
M_r = 360.79	F(000) = 372
Triclinic, P1	D_x = 1.383 Mg m⁻³
a = 9.2846 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8777 (10) Å	Cell parameters from 4550 reflections
c = 10.3624 (11) Å	θ = 2.5–29.4°
α = 94.364 (2)°	µ = 0.24 mm⁻¹
β = 113.3517 (19)°	T = 296 K
γ = 92.866 (2)°	Plate, yellow
V = 866.63 (15) Å³	0.43 × 0.39 × 0.11 mm

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Data collection

Bruker SMART APEXII DUO CCD diffractometer	2973 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
φ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.905, T_max = 0.974	k = −12→12
15408 measured reflections	l = −13→13
3917 independent reflections

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Refinement

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0894P)² + 0.1829P] where P = (F_o² + 2F_c²)/3
3917 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

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Special details

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.

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

	x	y	z	U_iso*/U_eq
F1	0.34800 (14)	0.90969 (12)	0.72673 (15)	0.0699 (4)
Cl1	0.88071 (6)	0.82117 (5)	1.09430 (6)	0.0677 (2)
O1	0.52128 (16)	0.43191 (13)	0.84772 (16)	0.0550 (4)
C1	0.4948 (2)	0.95649 (18)	0.8188 (2)	0.0458 (4)
C2	0.5336 (3)	1.09407 (19)	0.8323 (2)	0.0550 (5)
H2A	0.4608	1.1517	0.7807	0.066*
C3	0.6821 (3)	1.14449 (19)	0.9237 (2)	0.0570 (5)
H3A	0.7116	1.2372	0.9327	0.068*
C4	0.7881 (2)	1.05996 (19)	1.0024 (2)	0.0526 (5)
H4A	0.8886	1.0950	1.0648	0.063*
C5	0.7438 (2)	0.92195 (17)	0.98776 (19)	0.0429 (4)
C6	0.5955 (2)	0.86314 (16)	0.89285 (17)	0.0380 (4)
C7	0.5552 (2)	0.71650 (16)	0.87498 (19)	0.0404 (4)
H7A	0.6308	0.6670	0.9364	0.048*
C8	0.4263 (2)	0.64341 (17)	0.7838 (2)	0.0434 (4)
H8A	0.3445	0.6871	0.7217	0.052*
C9	0.4112 (2)	0.49374 (17)	0.77988 (19)	0.0398 (4)
C10	0.2559 (2)	0.41801 (16)	0.68598 (18)	0.0382 (4)
C11	0.2509 (2)	0.31627 (17)	0.58084 (18)	0.0417 (4)
C12	0.3822 (3)	0.2912 (2)	0.5479 (2)	0.0565 (5)
H12A	0.4763	0.3456	0.5947	0.068*
C13	0.3721 (3)	0.1887 (3)	0.4489 (3)	0.0718 (7)
H13A	0.4600	0.1736	0.4295	0.086*
C14	0.2325 (4)	0.1053 (3)	0.3755 (3)	0.0800 (8)
H14A	0.2291	0.0344	0.3096	0.096*
C15	0.1029 (3)	0.1272 (3)	0.3997 (2)	0.0700 (6)
H15A	0.0103	0.0718	0.3496	0.084*
C16	0.1060 (2)	0.23471 (19)	0.50155 (19)	0.0496 (4)
C17	−0.0258 (2)	0.2597 (2)	0.5264 (2)	0.0551 (5)
H17A	−0.1191	0.2055	0.4748	0.066*
C18	−0.0244 (2)	0.3629 (2)	0.6260 (2)	0.0479 (4)
C19	−0.1599 (2)	0.3878 (3)	0.6524 (3)	0.0683 (6)
H19A	−0.2546	0.3364	0.5986	0.082*
C20	−0.1546 (3)	0.4844 (3)	0.7537 (3)	0.0756 (7)
H20A	−0.2455	0.5004	0.7677	0.091*
C21	−0.0121 (3)	0.5609 (2)	0.8381 (3)	0.0679 (6)
H21A	−0.0092	0.6263	0.9087	0.081*
C22	0.1212 (2)	0.5408 (2)	0.8184 (2)	0.0528 (5)
H22A	0.2147	0.5916	0.8769	0.063*
C23	0.1206 (2)	0.44299 (16)	0.70929 (18)	0.0397 (4)

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0491 (7)	0.0501 (7)	0.0787 (9)	0.0030 (5)	−0.0066 (6)	0.0012 (6)
Cl1	0.0519 (3)	0.0535 (3)	0.0713 (4)	−0.0034 (2)	−0.0026 (3)	0.0099 (2)
O1	0.0412 (7)	0.0393 (7)	0.0702 (9)	0.0012 (5)	0.0087 (6)	−0.0007 (6)
C1	0.0465 (10)	0.0396 (9)	0.0443 (9)	0.0005 (7)	0.0124 (8)	−0.0026 (7)
C2	0.0695 (13)	0.0368 (9)	0.0554 (11)	0.0083 (9)	0.0216 (10)	0.0036 (8)
C3	0.0770 (14)	0.0323 (9)	0.0588 (12)	−0.0059 (9)	0.0269 (11)	−0.0033 (8)
C4	0.0562 (11)	0.0411 (9)	0.0514 (11)	−0.0150 (8)	0.0166 (9)	−0.0070 (8)
C5	0.0447 (9)	0.0392 (8)	0.0405 (9)	−0.0053 (7)	0.0145 (7)	−0.0009 (7)
C6	0.0423 (9)	0.0335 (8)	0.0377 (8)	−0.0024 (6)	0.0170 (7)	−0.0011 (6)
C7	0.0403 (9)	0.0334 (8)	0.0452 (9)	−0.0010 (7)	0.0161 (7)	0.0006 (7)
C8	0.0388 (9)	0.0353 (8)	0.0504 (10)	−0.0022 (7)	0.0128 (8)	0.0026 (7)
C9	0.0368 (8)	0.0360 (8)	0.0455 (9)	−0.0032 (7)	0.0173 (7)	−0.0026 (7)
C10	0.0376 (8)	0.0336 (8)	0.0403 (8)	−0.0034 (6)	0.0137 (7)	0.0011 (6)
C11	0.0439 (9)	0.0408 (9)	0.0368 (8)	−0.0021 (7)	0.0136 (7)	0.0007 (7)
C12	0.0575 (12)	0.0626 (12)	0.0523 (11)	−0.0026 (10)	0.0281 (10)	−0.0063 (9)
C13	0.0805 (17)	0.0812 (16)	0.0618 (14)	0.0067 (13)	0.0405 (13)	−0.0115 (12)
C14	0.101 (2)	0.0781 (16)	0.0578 (14)	−0.0017 (15)	0.0358 (14)	−0.0256 (12)
C15	0.0773 (15)	0.0670 (14)	0.0508 (12)	−0.0131 (12)	0.0171 (11)	−0.0213 (10)
C16	0.0523 (11)	0.0490 (10)	0.0376 (9)	−0.0053 (8)	0.0102 (8)	−0.0034 (7)
C17	0.0403 (10)	0.0614 (12)	0.0475 (10)	−0.0108 (8)	0.0043 (8)	−0.0053 (9)
C18	0.0357 (9)	0.0537 (10)	0.0470 (10)	−0.0008 (7)	0.0096 (8)	0.0051 (8)
C19	0.0352 (10)	0.0876 (16)	0.0737 (15)	−0.0047 (10)	0.0160 (10)	−0.0008 (13)
C20	0.0488 (12)	0.0917 (18)	0.0939 (19)	0.0084 (12)	0.0379 (13)	0.0001 (15)
C21	0.0670 (14)	0.0652 (13)	0.0828 (16)	0.0050 (11)	0.0444 (13)	−0.0055 (12)
C22	0.0486 (10)	0.0475 (10)	0.0636 (12)	−0.0039 (8)	0.0273 (9)	−0.0080 (9)
C23	0.0383 (8)	0.0362 (8)	0.0422 (9)	−0.0005 (7)	0.0140 (7)	0.0040 (7)

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Geometric parameters (Å, º)

F1—C1	1.350 (2)	C12—C13	1.358 (3)
Cl1—C5	1.734 (2)	C12—H12A	0.9300
O1—C9	1.212 (2)	C13—C14	1.398 (4)
C1—C2	1.371 (3)	C13—H13A	0.9300
C1—C6	1.392 (3)	C14—C15	1.347 (4)
C2—C3	1.367 (3)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.430 (3)
C3—C4	1.371 (3)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.377 (3)
C4—C5	1.383 (2)	C17—C18	1.391 (3)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.400 (2)	C18—C19	1.419 (3)
C6—C7	1.457 (2)	C18—C23	1.432 (2)
C7—C8	1.326 (2)	C19—C20	1.348 (4)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.474 (2)	C20—C21	1.403 (4)
C8—H8A	0.9300	C20—H20A	0.9300
C9—C10	1.501 (2)	C21—C22	1.353 (3)
C10—C23	1.401 (2)	C21—H21A	0.9300
C10—C11	1.410 (2)	C22—C23	1.429 (3)
C11—C12	1.418 (3)	C22—H22A	0.9300
C11—C16	1.431 (2)

F1—C1—C2	116.89 (17)	C11—C12—H12A	119.6
F1—C1—C6	118.40 (15)	C12—C13—C14	121.4 (2)
C2—C1—C6	124.72 (18)	C12—C13—H13A	119.3
C3—C2—C1	118.30 (19)	C14—C13—H13A	119.3
C3—C2—H2A	120.9	C15—C14—C13	120.3 (2)
C1—C2—H2A	120.9	C15—C14—H14A	119.9
C2—C3—C4	120.80 (17)	C13—C14—H14A	119.9
C2—C3—H3A	119.6	C14—C15—C16	120.8 (2)
C4—C3—H3A	119.6	C14—C15—H15A	119.6
C3—C4—C5	119.26 (18)	C16—C15—H15A	119.6
C3—C4—H4A	120.4	C17—C16—C15	121.58 (19)
C5—C4—H4A	120.4	C17—C16—C11	119.60 (17)
C4—C5—C6	122.82 (17)	C15—C16—C11	118.81 (19)
C4—C5—Cl1	117.09 (14)	C16—C17—C18	122.30 (17)
C6—C5—Cl1	120.08 (13)	C16—C17—H17A	118.8
C1—C6—C5	114.05 (15)	C18—C17—H17A	118.8
C1—C6—C7	124.47 (16)	C17—C18—C19	122.26 (18)
C5—C6—C7	121.48 (16)	C17—C18—C23	118.89 (17)
C8—C7—C6	129.39 (17)	C19—C18—C23	118.79 (18)
C8—C7—H7A	115.3	C20—C19—C18	121.4 (2)
C6—C7—H7A	115.3	C20—C19—H19A	119.3
C7—C8—C9	120.76 (17)	C18—C19—H19A	119.3
C7—C8—H8A	119.6	C19—C20—C21	120.1 (2)
C9—C8—H8A	119.6	C19—C20—H20A	120.0
O1—C9—C8	121.54 (15)	C21—C20—H20A	120.0
O1—C9—C10	120.20 (15)	C22—C21—C20	121.0 (2)
C8—C9—C10	118.24 (15)	C22—C21—H21A	119.5
C23—C10—C11	120.91 (15)	C20—C21—H21A	119.5
C23—C10—C9	119.90 (14)	C21—C22—C23	121.0 (2)
C11—C10—C9	119.07 (15)	C21—C22—H22A	119.5
C10—C11—C12	123.31 (16)	C23—C22—H22A	119.5
C10—C11—C16	118.82 (16)	C10—C23—C22	122.97 (16)
C12—C11—C16	117.86 (16)	C10—C23—C18	119.40 (16)
C13—C12—C11	120.8 (2)	C22—C23—C18	117.55 (16)
C13—C12—H12A	119.6

F1—C1—C2—C3	−179.33 (18)	C11—C12—C13—C14	0.5 (4)
C6—C1—C2—C3	0.7 (3)	C12—C13—C14—C15	1.5 (4)
C1—C2—C3—C4	−1.6 (3)	C13—C14—C15—C16	−0.7 (4)
C2—C3—C4—C5	0.5 (3)	C14—C15—C16—C17	179.2 (2)
C3—C4—C5—C6	1.7 (3)	C14—C15—C16—C11	−1.9 (4)
C3—C4—C5—Cl1	−177.92 (16)	C10—C11—C16—C17	1.9 (3)
F1—C1—C6—C5	−178.72 (16)	C12—C11—C16—C17	−177.37 (19)
C2—C1—C6—C5	1.2 (3)	C10—C11—C16—C15	−177.00 (19)
F1—C1—C6—C7	1.9 (3)	C12—C11—C16—C15	3.7 (3)
C2—C1—C6—C7	−178.11 (18)	C15—C16—C17—C18	179.4 (2)
C4—C5—C6—C1	−2.4 (2)	C11—C16—C17—C18	0.5 (3)
Cl1—C5—C6—C1	177.15 (13)	C16—C17—C18—C19	−179.5 (2)
C4—C5—C6—C7	176.95 (17)	C16—C17—C18—C23	−2.3 (3)
Cl1—C5—C6—C7	−3.5 (2)	C17—C18—C19—C20	177.0 (2)
C1—C6—C7—C8	4.7 (3)	C23—C18—C19—C20	−0.1 (4)
C5—C6—C7—C8	−174.62 (18)	C18—C19—C20—C21	−1.5 (4)
C6—C7—C8—C9	177.73 (16)	C19—C20—C21—C22	1.0 (4)
C7—C8—C9—O1	−8.3 (3)	C20—C21—C22—C23	1.2 (4)
C7—C8—C9—C10	173.29 (16)	C11—C10—C23—C22	177.24 (17)
O1—C9—C10—C23	120.22 (19)	C9—C10—C23—C22	1.3 (3)
C8—C9—C10—C23	−61.4 (2)	C11—C10—C23—C18	0.7 (3)
O1—C9—C10—C11	−55.8 (2)	C9—C10—C23—C18	−175.30 (15)
C8—C9—C10—C11	122.59 (18)	C21—C22—C23—C10	−179.4 (2)
C23—C10—C11—C12	176.76 (17)	C21—C22—C23—C18	−2.8 (3)
C9—C10—C11—C12	−7.2 (3)	C17—C18—C23—C10	1.7 (3)
C23—C10—C11—C16	−2.5 (3)	C19—C18—C23—C10	178.96 (19)
C9—C10—C11—C16	173.54 (16)	C17—C18—C23—C22	−175.05 (19)
C10—C11—C12—C13	177.7 (2)	C19—C18—C23—C22	2.2 (3)
C16—C11—C12—C13	−3.0 (3)

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Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···F1	0.93	2.19	2.808 (2)	123
C17—H17A···F1ⁱ	0.93	2.46	3.353 (2)	161
C14—H14A···Cg1ⁱⁱ	0.93	2.99	3.712 (3)	136

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

References

Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177–3180. [DOI] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Madan, B., Batra, S. & Ghosh, B. (2000). Mol. Pharmacol. 58, 526–534. [DOI] [PubMed]
Ngaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2011). Acta Cryst. E67, o169–o170. [DOI] [PMC free article] [PubMed]
Razak, I. A., Fun, H.-K., Ngaini, Z., Rahman, N. I. A. & Hussain, H. (2009). Acta Cryst. E65, o1439–o1440. [DOI] [PMC free article] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. University of Western Australia.
Xue, C. X., Cui, S. Y., Liu, M. C., Hu, D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745–753. [DOI] [PubMed]
Yayli, N., Ucuncu, O., Yasar, A., Kucuk, M., Yayli, N., Akyuz, E. & Alpay-Karaoglu, S. (2006). Turk. J. Chem. 30, 505–514.
Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Bioorg. Med. Chem. Lett. 15, 5027–5029. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016005028/hb7569sup1.cif

e-72-00648-sup1.cif^{(618.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016005028/hb7569Isup2.hkl

e-72-00648-Isup2.hkl^{(214.9KB, hkl)}

Click here for additional data file.^{(6.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989016005028/hb7569Isup3.cml

CCDC reference: 1470351

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177–3180. [DOI] [PubMed]

[bb2] Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

[bb3] Madan, B., Batra, S. & Ghosh, B. (2000). Mol. Pharmacol. 58, 526–534. [DOI] [PubMed]

[bb4] Ngaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2011). Acta Cryst. E67, o169–o170. [DOI] [PMC free article] [PubMed]

[bb5] Razak, I. A., Fun, H.-K., Ngaini, Z., Rahman, N. I. A. & Hussain, H. (2009). Acta Cryst. E65, o1439–o1440. [DOI] [PMC free article] [PubMed]

[bb6] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb7] Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.

[bb9] Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. University of Western Australia.

[bb10] Xue, C. X., Cui, S. Y., Liu, M. C., Hu, D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745–753. [DOI] [PubMed]

[bb11] Yayli, N., Ucuncu, O., Yasar, A., Kucuk, M., Yayli, N., Akyuz, E. & Alpay-Karaoglu, S. (2006). Turk. J. Chem. 30, 505–514.

[bb12] Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Bioorg. Med. Chem. Lett. 15, 5027–5029. [DOI] [PubMed]

PERMALINK

(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluoro­phen­yl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis

Amzar Ahlami Abdullah

Nur Hafiq Hanif Hassan

Suhana Arshad

Nuridayanti Che Khalib

Ibrahim Abdul Razak

Abstract

Chemical context

Structural commentary

Figure 1.

Supra­molecular features

Figure 2.

Table 1. Hydrogen-bond geometry (Å, °).

Figure 3.

Hirshfeld surfaces analysis

Figure 4.

Figure 5.

Figure 6.

Figure 7.

Synthesis and crystallization

Refinement details

Table 2. Experimental details.

Supplementary Material

Acknowledgments

supplementary crystallographic information

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, º)

Hydrogen-bond geometry (Å, º)

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis

Supramolecular features

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

Atomic displacement parameters (Å²)