research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 648-651

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

CROSSMARK_Color_square_no_text.svg

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 February 2016; accepted 24 March 2016; online 8 April 2016)

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 ππ inter­actions. Hirshfeld surface analysis was used to confirm the existence of inter­molecular inter­actions.

1. Chemical context

The biological properties of chalcone derivatives such as anti­cancer (Bhat et al., 2005[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.]), anti­malarial (Xue et al., 2004[Xue, C. X., Cui, S. Y., Liu, M. C., Hu, D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745-753.]), anti-oxidant and anti­microbial (Yayli et al., 2006[Yayli, N., Ucuncu, O., Yasar, A., Kucuk, M., Yayli, N., Akyuz, E. & Alpay-Karaoglu, S. (2006). Turk. J. Chem. 30, 505-514.]), anti­platelet (Zhao et al., 2005[Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Bioorg. Med. Chem. Lett. 15, 5027-5029.]) as well as anti-inflammatory (Madan et al., 2000[Madan, B., Batra, S. & Ghosh, B. (2000). Mol. Pharmacol. 58, 526-534.]) 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.

[Scheme 1]

2. Structural commentary

The mol­ecular structure of the title chalcone is shown in Fig. 1[link]. 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[Razak, I. A., Fun, H.-K., Ngaini, Z., Rahman, N. I. A. & Hussain, H. (2009). Acta Cryst. E65, o1439-o1440.]; Ngaini et al., 2011[Ngaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2011). Acta Cryst. E67, o169-o170.]).

[Figure 1]
Figure 1
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.

3. Supra­molecular features

In the crystal (Fig. 2[link]), the mol­ecules are arranged into centrosymmetric dimers via pairs of C17—H17A⋯F1 (Table 1[link]) hydrogen bonds. The crystal structure also features C14—H14ACg1 (Fig. 3[link]) 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].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA 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—H14ACg1ii 0.93 2.99 3.712 (3) 136
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
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.
[Figure 3]
Figure 3
Detail of the crystal structure showing the C14—H14ACg1 inter­action where Cg1 is the centroid of C1–C6 ring.

4. Hirshfeld surfaces analysis

The inter­molecular inter­actions of the title compound can be visualized using Hirshfeld surface analysis (Wolff et al., 2012[Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. University of Western Australia.]). The Hirshfeld surfaces mapped over dnorm are shown in Fig. 4[link]. The 2-D fingerprint plots showing the occurrence of different kinds of inter­molecular contacts are shown in Fig. 5[link].

[Figure 4]
Figure 4
dnorm mapped on the Hirshfeld surface for visualizing the inter­molecular inter­actions of the title chalcone compound. Dotted lines (green) represent hydrogen bonds.
[Figure 5]
Figure 5
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 de + di ∼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 de + di. 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 de + di ∼2.6 Å on the fingerprint plot. The presence of ππ 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[link]) and the Hirshfeld surfaces mapped with curvedness (Fig. 7[link]).

[Figure 6]
Figure 6
Hirshfeld surface mapped over the shape index of the chalcone compound in (a) front view and (b) back view.
[Figure 7]
Figure 7
Hirshfeld surface mapped over curvedness of the chalcone compound in (a) front view and (b) back view.

5. 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.

6. Refinement details

Crystal data collection and structure refinement details are summarized in Table 2[link]. All H atoms were positioned geometrically (C—H = 0.93 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(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
Mr 360.79
Crystal system, space group Triclinic, P[\overline{1}]
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)
V3) 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.905, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections 15408, 3917, 2973
Rint 0.027
(sin θ/λ)max−1) 0.650
 
Refinement
R[F2 > 2σ(F2)], wR(F2), 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
Δρmax, Δρmin (e Å−3) 0.27, −0.38
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Supporting information


Chemical context top

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 top

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).

Supra­molecular features top

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].

Hirshfeld surfaces analysis top

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

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 de + di ~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 de + di. 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 de + di ~2.6 Å on the fingerprint plot. The presence of ππ 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).

Synthesis and crystallization top

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 top

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 Uiso(H) = 1.2Ueq(C). The most disagreeable reflections (-1 -2 4 and -1 1 0) were omitted from the final refinement.

Related literature top

For general background of chalcone derivatives, see: Bhat et al. (2004); Zhao et al. (2005); Madan et al. (2000); Xue et al. (2004) and Yayli et al. (2006). For hydrogen- bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see: Razak et al. (2009) and Ngaini et al. (2011).

Structure description top

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.

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).

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

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 de + di ~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 de + di. 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 de + di ~2.6 Å on the fingerprint plot. The presence of ππ 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).

For general background of chalcone derivatives, see: Bhat et al. (2004); Zhao et al. (2005); Madan et al. (2000); Xue et al. (2004) and Yayli et al. (2006). For hydrogen- bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see: Razak et al. (2009) and Ngaini et al. (2011).

Synthesis and crystallization top

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 top

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 Uiso(H) = 1.2Ueq(C). The most disagreeable reflections (-1 -2 4 and -1 1 0) were omitted from the final refinement.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. 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.
[Figure 2] Fig. 2. 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.
[Figure 3] Fig. 3. Detail of the crystal structure showing the C14—H14A···Cg1 interaction where Cg1 is the centroid of C1–C6 ring.
[Figure 4] Fig. 4. dnorm mapped on the Hirshfeld surface for visualizing the intermolecular interactions of the title chalcone compound. Dotted lines (green) represent hydrogen bonds.
[Figure 5] Fig. 5. The 2-Dimensional fingerprint plot for the title chalcone compound showing contributions from different contacts.
[Figure 6] Fig. 6. Hirshfeld surface mapped over the shape index of the chalcone compound in (a) front view and (b) back view.
[Figure 7] Fig. 7. Hirshfeld surface mapped over curvedness of the chalcone compound in (a) front view and (b) back view.
(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one top
Crystal data top
C23H14ClFOZ = 2
Mr = 360.79F(000) = 372
Triclinic, P1Dx = 1.383 Mg m3
a = 9.2846 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8777 (10) ÅCell parameters from 4550 reflections
c = 10.3624 (11) Åθ = 2.5–29.4°
α = 94.364 (2)°µ = 0.24 mm1
β = 113.3517 (19)°T = 296 K
γ = 92.866 (2)°Plate, yellow
V = 866.63 (15) Å30.43 × 0.39 × 0.11 mm
Data collection top
Bruker SMART APEXII DUO CCD
diffractometer
2973 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1212
Tmin = 0.905, Tmax = 0.974k = 1212
15408 measured reflectionsl = 1313
3917 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0894P)2 + 0.1829P]
where P = (Fo2 + 2Fc2)/3
3917 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C23H14ClFOγ = 92.866 (2)°
Mr = 360.79V = 866.63 (15) Å3
Triclinic, P1Z = 2
a = 9.2846 (9) ÅMo Kα radiation
b = 9.8777 (10) ŵ = 0.24 mm1
c = 10.3624 (11) ÅT = 296 K
α = 94.364 (2)°0.43 × 0.39 × 0.11 mm
β = 113.3517 (19)°
Data collection top
Bruker SMART APEXII DUO CCD
diffractometer
3917 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2973 reflections with I > 2σ(I)
Tmin = 0.905, Tmax = 0.974Rint = 0.027
15408 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.27 e Å3
3917 reflectionsΔρmin = 0.38 e Å3
235 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.34800 (14)0.90969 (12)0.72673 (15)0.0699 (4)
Cl10.88071 (6)0.82117 (5)1.09430 (6)0.0677 (2)
O10.52128 (16)0.43191 (13)0.84772 (16)0.0550 (4)
C10.4948 (2)0.95649 (18)0.8188 (2)0.0458 (4)
C20.5336 (3)1.09407 (19)0.8323 (2)0.0550 (5)
H2A0.46081.15170.78070.066*
C30.6821 (3)1.14449 (19)0.9237 (2)0.0570 (5)
H3A0.71161.23720.93270.068*
C40.7881 (2)1.05996 (19)1.0024 (2)0.0526 (5)
H4A0.88861.09501.06480.063*
C50.7438 (2)0.92195 (17)0.98776 (19)0.0429 (4)
C60.5955 (2)0.86314 (16)0.89285 (17)0.0380 (4)
C70.5552 (2)0.71650 (16)0.87498 (19)0.0404 (4)
H7A0.63080.66700.93640.048*
C80.4263 (2)0.64341 (17)0.7838 (2)0.0434 (4)
H8A0.34450.68710.72170.052*
C90.4112 (2)0.49374 (17)0.77988 (19)0.0398 (4)
C100.2559 (2)0.41801 (16)0.68598 (18)0.0382 (4)
C110.2509 (2)0.31627 (17)0.58084 (18)0.0417 (4)
C120.3822 (3)0.2912 (2)0.5479 (2)0.0565 (5)
H12A0.47630.34560.59470.068*
C130.3721 (3)0.1887 (3)0.4489 (3)0.0718 (7)
H13A0.46000.17360.42950.086*
C140.2325 (4)0.1053 (3)0.3755 (3)0.0800 (8)
H14A0.22910.03440.30960.096*
C150.1029 (3)0.1272 (3)0.3997 (2)0.0700 (6)
H15A0.01030.07180.34960.084*
C160.1060 (2)0.23471 (19)0.50155 (19)0.0496 (4)
C170.0258 (2)0.2597 (2)0.5264 (2)0.0551 (5)
H17A0.11910.20550.47480.066*
C180.0244 (2)0.3629 (2)0.6260 (2)0.0479 (4)
C190.1599 (2)0.3878 (3)0.6524 (3)0.0683 (6)
H19A0.25460.33640.59860.082*
C200.1546 (3)0.4844 (3)0.7537 (3)0.0756 (7)
H20A0.24550.50040.76770.091*
C210.0121 (3)0.5609 (2)0.8381 (3)0.0679 (6)
H21A0.00920.62630.90870.081*
C220.1212 (2)0.5408 (2)0.8184 (2)0.0528 (5)
H22A0.21470.59160.87690.063*
C230.1206 (2)0.44299 (16)0.70929 (18)0.0397 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0491 (7)0.0501 (7)0.0787 (9)0.0030 (5)0.0066 (6)0.0012 (6)
Cl10.0519 (3)0.0535 (3)0.0713 (4)0.0034 (2)0.0026 (3)0.0099 (2)
O10.0412 (7)0.0393 (7)0.0702 (9)0.0012 (5)0.0087 (6)0.0007 (6)
C10.0465 (10)0.0396 (9)0.0443 (9)0.0005 (7)0.0124 (8)0.0026 (7)
C20.0695 (13)0.0368 (9)0.0554 (11)0.0083 (9)0.0216 (10)0.0036 (8)
C30.0770 (14)0.0323 (9)0.0588 (12)0.0059 (9)0.0269 (11)0.0033 (8)
C40.0562 (11)0.0411 (9)0.0514 (11)0.0150 (8)0.0166 (9)0.0070 (8)
C50.0447 (9)0.0392 (8)0.0405 (9)0.0053 (7)0.0145 (7)0.0009 (7)
C60.0423 (9)0.0335 (8)0.0377 (8)0.0024 (6)0.0170 (7)0.0011 (6)
C70.0403 (9)0.0334 (8)0.0452 (9)0.0010 (7)0.0161 (7)0.0006 (7)
C80.0388 (9)0.0353 (8)0.0504 (10)0.0022 (7)0.0128 (8)0.0026 (7)
C90.0368 (8)0.0360 (8)0.0455 (9)0.0032 (7)0.0173 (7)0.0026 (7)
C100.0376 (8)0.0336 (8)0.0403 (8)0.0034 (6)0.0137 (7)0.0011 (6)
C110.0439 (9)0.0408 (9)0.0368 (8)0.0021 (7)0.0136 (7)0.0007 (7)
C120.0575 (12)0.0626 (12)0.0523 (11)0.0026 (10)0.0281 (10)0.0063 (9)
C130.0805 (17)0.0812 (16)0.0618 (14)0.0067 (13)0.0405 (13)0.0115 (12)
C140.101 (2)0.0781 (16)0.0578 (14)0.0017 (15)0.0358 (14)0.0256 (12)
C150.0773 (15)0.0670 (14)0.0508 (12)0.0131 (12)0.0171 (11)0.0213 (10)
C160.0523 (11)0.0490 (10)0.0376 (9)0.0053 (8)0.0102 (8)0.0034 (7)
C170.0403 (10)0.0614 (12)0.0475 (10)0.0108 (8)0.0043 (8)0.0053 (9)
C180.0357 (9)0.0537 (10)0.0470 (10)0.0008 (7)0.0096 (8)0.0051 (8)
C190.0352 (10)0.0876 (16)0.0737 (15)0.0047 (10)0.0160 (10)0.0008 (13)
C200.0488 (12)0.0917 (18)0.0939 (19)0.0084 (12)0.0379 (13)0.0001 (15)
C210.0670 (14)0.0652 (13)0.0828 (16)0.0050 (11)0.0444 (13)0.0055 (12)
C220.0486 (10)0.0475 (10)0.0636 (12)0.0039 (8)0.0273 (9)0.0080 (9)
C230.0383 (8)0.0362 (8)0.0422 (9)0.0005 (7)0.0140 (7)0.0040 (7)
Geometric parameters (Å, º) top
F1—C11.350 (2)C12—C131.358 (3)
Cl1—C51.734 (2)C12—H12A0.9300
O1—C91.212 (2)C13—C141.398 (4)
C1—C21.371 (3)C13—H13A0.9300
C1—C61.392 (3)C14—C151.347 (4)
C2—C31.367 (3)C14—H14A0.9300
C2—H2A0.9300C15—C161.430 (3)
C3—C41.371 (3)C15—H15A0.9300
C3—H3A0.9300C16—C171.377 (3)
C4—C51.383 (2)C17—C181.391 (3)
C4—H4A0.9300C17—H17A0.9300
C5—C61.400 (2)C18—C191.419 (3)
C6—C71.457 (2)C18—C231.432 (2)
C7—C81.326 (2)C19—C201.348 (4)
C7—H7A0.9300C19—H19A0.9300
C8—C91.474 (2)C20—C211.403 (4)
C8—H8A0.9300C20—H20A0.9300
C9—C101.501 (2)C21—C221.353 (3)
C10—C231.401 (2)C21—H21A0.9300
C10—C111.410 (2)C22—C231.429 (3)
C11—C121.418 (3)C22—H22A0.9300
C11—C161.431 (2)
F1—C1—C2116.89 (17)C11—C12—H12A119.6
F1—C1—C6118.40 (15)C12—C13—C14121.4 (2)
C2—C1—C6124.72 (18)C12—C13—H13A119.3
C3—C2—C1118.30 (19)C14—C13—H13A119.3
C3—C2—H2A120.9C15—C14—C13120.3 (2)
C1—C2—H2A120.9C15—C14—H14A119.9
C2—C3—C4120.80 (17)C13—C14—H14A119.9
C2—C3—H3A119.6C14—C15—C16120.8 (2)
C4—C3—H3A119.6C14—C15—H15A119.6
C3—C4—C5119.26 (18)C16—C15—H15A119.6
C3—C4—H4A120.4C17—C16—C15121.58 (19)
C5—C4—H4A120.4C17—C16—C11119.60 (17)
C4—C5—C6122.82 (17)C15—C16—C11118.81 (19)
C4—C5—Cl1117.09 (14)C16—C17—C18122.30 (17)
C6—C5—Cl1120.08 (13)C16—C17—H17A118.8
C1—C6—C5114.05 (15)C18—C17—H17A118.8
C1—C6—C7124.47 (16)C17—C18—C19122.26 (18)
C5—C6—C7121.48 (16)C17—C18—C23118.89 (17)
C8—C7—C6129.39 (17)C19—C18—C23118.79 (18)
C8—C7—H7A115.3C20—C19—C18121.4 (2)
C6—C7—H7A115.3C20—C19—H19A119.3
C7—C8—C9120.76 (17)C18—C19—H19A119.3
C7—C8—H8A119.6C19—C20—C21120.1 (2)
C9—C8—H8A119.6C19—C20—H20A120.0
O1—C9—C8121.54 (15)C21—C20—H20A120.0
O1—C9—C10120.20 (15)C22—C21—C20121.0 (2)
C8—C9—C10118.24 (15)C22—C21—H21A119.5
C23—C10—C11120.91 (15)C20—C21—H21A119.5
C23—C10—C9119.90 (14)C21—C22—C23121.0 (2)
C11—C10—C9119.07 (15)C21—C22—H22A119.5
C10—C11—C12123.31 (16)C23—C22—H22A119.5
C10—C11—C16118.82 (16)C10—C23—C22122.97 (16)
C12—C11—C16117.86 (16)C10—C23—C18119.40 (16)
C13—C12—C11120.8 (2)C22—C23—C18117.55 (16)
C13—C12—H12A119.6
F1—C1—C2—C3179.33 (18)C11—C12—C13—C140.5 (4)
C6—C1—C2—C30.7 (3)C12—C13—C14—C151.5 (4)
C1—C2—C3—C41.6 (3)C13—C14—C15—C160.7 (4)
C2—C3—C4—C50.5 (3)C14—C15—C16—C17179.2 (2)
C3—C4—C5—C61.7 (3)C14—C15—C16—C111.9 (4)
C3—C4—C5—Cl1177.92 (16)C10—C11—C16—C171.9 (3)
F1—C1—C6—C5178.72 (16)C12—C11—C16—C17177.37 (19)
C2—C1—C6—C51.2 (3)C10—C11—C16—C15177.00 (19)
F1—C1—C6—C71.9 (3)C12—C11—C16—C153.7 (3)
C2—C1—C6—C7178.11 (18)C15—C16—C17—C18179.4 (2)
C4—C5—C6—C12.4 (2)C11—C16—C17—C180.5 (3)
Cl1—C5—C6—C1177.15 (13)C16—C17—C18—C19179.5 (2)
C4—C5—C6—C7176.95 (17)C16—C17—C18—C232.3 (3)
Cl1—C5—C6—C73.5 (2)C17—C18—C19—C20177.0 (2)
C1—C6—C7—C84.7 (3)C23—C18—C19—C200.1 (4)
C5—C6—C7—C8174.62 (18)C18—C19—C20—C211.5 (4)
C6—C7—C8—C9177.73 (16)C19—C20—C21—C221.0 (4)
C7—C8—C9—O18.3 (3)C20—C21—C22—C231.2 (4)
C7—C8—C9—C10173.29 (16)C11—C10—C23—C22177.24 (17)
O1—C9—C10—C23120.22 (19)C9—C10—C23—C221.3 (3)
C8—C9—C10—C2361.4 (2)C11—C10—C23—C180.7 (3)
O1—C9—C10—C1155.8 (2)C9—C10—C23—C18175.30 (15)
C8—C9—C10—C11122.59 (18)C21—C22—C23—C10179.4 (2)
C23—C10—C11—C12176.76 (17)C21—C22—C23—C182.8 (3)
C9—C10—C11—C127.2 (3)C17—C18—C23—C101.7 (3)
C23—C10—C11—C162.5 (3)C19—C18—C23—C10178.96 (19)
C9—C10—C11—C16173.54 (16)C17—C18—C23—C22175.05 (19)
C10—C11—C12—C13177.7 (2)C19—C18—C23—C222.2 (3)
C16—C11—C12—C133.0 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8A···F10.932.192.808 (2)123
C17—H17A···F1i0.932.463.353 (2)161
C14—H14A···Cg1ii0.932.993.712 (3)136
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8A···F10.932.192.808 (2)123
C17—H17A···F1i0.932.463.353 (2)161
C14—H14A···Cg1ii0.932.993.712 (3)136
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC23H14ClFO
Mr360.79
Crystal system, space groupTriclinic, P1
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)
V3)866.63 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.43 × 0.39 × 0.11
Data collection
DiffractometerBruker SMART APEXII DUO CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.905, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
15408, 3917, 2973
Rint0.027
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.159, 1.04
No. of reflections3917
No. of parameters235
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.38

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

 

Footnotes

Thomson Reuters ResearcherID: F-9119-2012.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

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

References

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Volume 72| Part 5| May 2016| Pages 648-651
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