research communications
(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one: and Hirshfeld surface analysis
aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my
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 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.
CCDC reference: 1470351
1. 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 of the title compound.
2. 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).
3. 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 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].
4. 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 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 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).
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. details
Crystal data collection and structure . 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.
details are summarized in Table 2Supporting information
CCDC reference: 1470351
10.1107/S2056989016005028/hb7569sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016005028/hb7569Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016005028/hb7569Isup3.cml
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
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
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 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).
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.
Crystal data collection and structure
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.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
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
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 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).
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).
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.
detailsCrystal data collection and structure
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.Data collection: APEX2 (Bruker, 2009); cell
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).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. | |
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. | |
Fig. 3. Detail of the crystal structure showing the C14—H14A···Cg1 interaction where Cg1 is the centroid of C1–C6 ring. | |
Fig. 4. dnorm mapped on the Hirshfeld surface for visualizing the intermolecular interactions of the title chalcone compound. Dotted lines (green) represent hydrogen bonds. | |
Fig. 5. The 2-Dimensional fingerprint plot for the title chalcone compound showing contributions from different contacts. | |
Fig. 6. Hirshfeld surface mapped over the shape index of the chalcone compound in (a) front view and (b) back view. | |
Fig. 7. Hirshfeld surface mapped over curvedness of the chalcone compound in (a) front view and (b) back view. |
C23H14ClFO | Z = 2 |
Mr = 360.79 | F(000) = 372 |
Triclinic, P1 | Dx = 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 |
Bruker SMART APEXII DUO CCD diffractometer | 2973 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→12 |
Tmin = 0.905, Tmax = 0.974 | k = −12→12 |
15408 measured reflections | l = −13→13 |
3917 independent reflections |
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(Fo2) + (0.0894P)2 + 0.1829P] where P = (Fo2 + 2Fc2)/3 |
3917 reflections | (Δ/σ)max = 0.001 |
235 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C23H14ClFO | γ = 92.866 (2)° |
Mr = 360.79 | V = 866.63 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.2846 (9) Å | Mo Kα radiation |
b = 9.8777 (10) Å | µ = 0.24 mm−1 |
c = 10.3624 (11) Å | T = 296 K |
α = 94.364 (2)° | 0.43 × 0.39 × 0.11 mm |
β = 113.3517 (19)° |
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 = 0.974 | Rint = 0.027 |
15408 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.27 e Å−3 |
3917 reflections | Δρmin = −0.38 e Å−3 |
235 parameters |
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 | Uiso*/Ueq | ||
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) |
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) |
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) |
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 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
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 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H14ClFO |
Mr | 360.79 |
Crystal system, space group | Triclinic, 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) |
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) |
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 (Å−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 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015).
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
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