Crystal structure and Hirshfeld surface analysis of a chalcone derivative: (E)-3-(4-fluoro­phen­yl)-1-(4-nitro­phen­yl)prop-2-en-1-one

Wong, Q.A.; Chia, T.S.; Kwong, H.C.; Chidan Kumar, C.S.; Quah, C.K.; Arafath, M.A.

doi:10.1107/S2056989018017450

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 75| Part 1| January 2019| Pages 53-57

https://doi.org/10.1107/S2056989018017450

Open

access

Crystal structure and Hirshfeld surface analysis of a chalcone derivative: (E)-3-(4-fluorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Qin Ai Wong,^a Tze Shyang Chia,^a ‡ Huey Chong Kwong,^b C. S. Chidan Kumar,^c ^* Ching Kheng Quah ^a § and Md. Azharul Arafath ^d ^*

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^cDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering and Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570 028, India, and ^dDepartment of Chemistry, Shahjalal University of Science and Technology, Sylhet, 3114, Bangladesh
^*Correspondence e-mail: chidankumar@gmail.com, arafath_sustche90@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 22 November 2018; accepted 10 December 2018; online 1 January 2019)

The molecular structure of the title chalcone derivative, C₁₅H₁₀FNO₃, is nearly planar and the molecule adopts a trans configuration with respect to the C=C double bond. The nitro group is nearly coplanar with the attached benzene ring, which is nearly parallel to the second benzene ring. In the crystal, molecules are connected by pairs of weak intermolecular C—H⋯O hydrogen bonds into inversion dimers. The dimers are further linked by another C—H⋯O hydrogen bond and a C—H⋯F hydrogen bond into sheets parallel to (104). π–π interactions occur between the sheets, with a centroid–centroid distance of 3.8860 (11) Å. Hirshfeld surface analysis was used to investigate and quantify the intermolecular interactions.

Keywords: crystal structure; chalcone; hydrogen bond; Hirshfeld surface analysis.

CCDC reference: 1036743

1. Chemical context

Non-linear optics (NLO) is the study of interactions between intense light and matter, in which the dielectric polarization responds non-linearly to the electric field of the light. This non-linearity leads to frequency-mixing processes (second-, third- and high-harmonic generations), the optical Kerr effect etc (Boulanger & Zyss, 2006 ). Chalcone is one of the NLO materials and is known for its high NLO coefficients and good crystallizability (Prabhu et al., 2013 ). Donor–acceptor substituted chalcone derivatives consist of two substituted phenyl rings covalently bonded to the ends of a α,β-unsaturated propenone bridge (C=C—C=O), which provides the necessary configuration for intramolecular charge transfer to show NLO properties (Fun et al., 2011 ). However, organic chalcone derivatives with a low melting point are at a disadvantage for applications as optical instruments. In a continuation of our ongoing studies on non-linear optical properties of various chalcone derivatives (Chandra Shekhara Shetty et al., 2017 ; Ekbote et al., 2017 ; Kwong et al., 2018 ), we report herein the synthesis, structure determination and Hirshfeld surface analysis of the title compound.

2. Structural commentary

The asymmetric unit of the title chalcone derivative consists of a unique molecule, containing two para-substituted phenyl rings and an enone connecting bridge (Fig. 1). The molecule adopts a trans configuration with respect to the C8=C9 olefinic double bond, as indicated by the C7—C8—C9—C10 torsion angle of −179.96 (15)°. The C7=O3 carbonyl group adopts an s-cis configuration with respect to the C8=C9 double bond as indicated by O3—C7—C8—C9 torsion angle of −0.8 (3)°. The molecule (excluding H atoms) is nearly planar with a maximum deviation of 0.103 (2) Å at atom O1 of the terminal nitro group. The nitro group is nearly coplanar with the attached C1–C6 benzene ring as indicated by the small dihedral angle of 7.9 (2)°. The C1–C6 and C10–C15 benzene rings make a small dihedral angle of 4.27 (8)° with each other.

Figure 1
The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids.

3. Supramolecular features

In the crystal, molecules are connected by pairs of weak C—H⋯O hydrogen bonds (C11—H11A⋯O3ⁱⁱ; symmetry code as in Table 1) into inversion dimers with an R₂²(14) ring motif. These dimers are further linked by C—H⋯O and C—H⋯F hydrogen bonds (C15—H15A⋯O1ⁱⁱⁱ and C4—H4A⋯F1ⁱ; Table 1) into two-dimensional sheets parallel to (104) (Fig. 2). Weak π–π interactions occur between the sheets [Cg1⋯Cg1^iv,v and Cg2⋯Cg2^iv,v = 3.8860 (11) Å, where Cg1 and Cg2 are the centroids of C1–C6 and C10–C15 benzene rings, respectively; symmetry codes: (iv) x − 1, y, z; (v) x + 1, y, z] (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯F1ⁱ	0.93	2.53	3.183 (2)	128
C11—H11A⋯O3ⁱⁱ	0.93	2.43	3.329 (2)	161
C15—H15A⋯O1ⁱⁱⁱ	0.93	2.58	3.489 (2)	166
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+1, -z+1; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
A partial packing diagram of the title compound, showing a two-dimensional sheet formed by C—H⋯O and C—H⋯F hydrogen bonds (dotted lines). H atoms not involved in hydrogen bonding are omitted for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) −x + 2, −y + 1, −z + 1; (iii) −x, y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

Figure 3
A partial packing diagram of the title compound, showing three separated sheets parallel to (104). The intermolecular π–π interactions between adjacent sheets are represented as red and blue dashed lines, involving Cg1⋯Cg1 and Cg2⋯Cg2, respectively. Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

4. Hirshfeld surface analysis

The Hirsheld surfaces mapped with normalized contact distance d_norm and electrostatic potentials, and the two-dimensional fingerprint plot were generated using CrystalExplorer (Version 17.5; Spackman & Jayatilaka, 2009 ; Spackman & McKinnon, 2002 ; Spackman et al., 2008 ; Turner et al., 2017 ). The darkest red spots on the Hirshfeld surface mapped with d_norm [Fig. 4(a)] correspond to the C11—H11A⋯O3 hydrogen bond. The C4—H4A⋯F1 and C15—H15A⋯O1 hydrogen bonds are indicated as two pairs of lighter red spots on the d_norm surface. The H12A⋯F1 contact, with its H⋯F distance shorter than the sum of van der Waals radii by 0.01 Å, appears as two tiny red spots on the d_norm surface. The donor and acceptor of a hydrogen bond with positive and negative electrostatic potentials, respectively, are represented as blue and red regions on the Hirshfeld surface mapped with electrostatic potential [Fig. 4(b)]. The electrostatic potential of the F atom is less negative as compared to the O atoms of nitro and carbonyl groups, as indicated by the lighter red region. The H⋯O/O⋯H contacts are the most populated contacts and contribute 30.2% of the total intermolecular contacts, followed by H⋯H (20.6%), H⋯C/C⋯H (18.0%), H⋯F/F⋯H (13.1%) and C⋯C (10.1%) contacts (Fig. 5). The shortest H⋯O/O⋯H and H⋯F/F⋯H contacts are represented as the tips of the pseudo-mirrored sharp spikes and blunt peaks at d_e + d_i ≃ 2.3 and 2.4 Å, respectively, which correspond to the C11—H11A⋯O3 and C4—H4A⋯F1 hydrogen bonds. The characteristic `wings' are missing in the fingerprint plot of H⋯C/C⋯H contacts, indicating the absence of any significant C—H⋯π interactions in the crystal. The C⋯C contacts, including the intermolecular π–π interactions, appear as a unique `triangle' focused at d_e ≃ d_i ≃ 1.8 Å. The presence of significant π–π interactions is supported by the unique pattern of red and blue `triangles' on the shape-index surface (Fig. 6), and the flat regions on the curvedness surface (Fig. 7) of the benzene rings.

Figure 4
The Hirshfeld surfaces mapped with (a) d_norm and (b) electrostatic potential for the central molecule of the title compound surrounded by six neighbouring molecules.

Figure 5
The two-dimensional fingerprint plots of the title compound for different intermolecular contacts and their percentage contributions to the Hirshfeld surface. d_i and d_e are the distances from the Hirshfeld surface to the nearest atom interior and exterior, respectively, to the surface.

Figure 6
(a) Front and (b) rear views of the Hirshfeld surface mapped over shape-index for the title compound. The dashed-line circles highlight unique patterns of red and blue `triangles'.

Figure 7
(a) Front and (b) rear views of the Hirshfeld surface mapped over curvedness.

5. Database survey

The bond lengths and bond angles of the title compound are comparable with those in two similar structures, viz., (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-one (refcode BUDXOO; Jing, 2009a ) and (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one (refcode BUDYOP; Jing, 2009b ) found in the Cambridge Structural Database (Version 5.39; Groom et al., 2016 ). The molecular conformations of these two structures are nearly planar, with small dihedral angles of 5.00 (6) and 10.60 (11)°, respectively, between the phenyl rings.

6. Synthesis and crystallization

4-Nitroacetophenone (1.65 g, 0.01 mol) and 4-fluorobenzaldehyde (1.24 g, 0.01 mol) were dissolved in methanol (20 ml). A catalytic amount of NaOH was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 6 h at room temperature. The progress of the reaction was monitored by TLC. The formed crude product was filtered, washed repeatedly with distilled water and recrystallized from ethanol to obtain the title chalcone derivative. Yellowish single-crystals suitable for X-ray diffraction were obtained from an acetone solution by slow evaporation at room temperature.

7. Refinement

Crystal data, 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).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀FNO₃
M_r	271.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	3.8860 (5), 13.2324 (16), 24.199 (3)
β (°)	91.963 (2)
V (Å³)	1243.6 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.49 × 0.35 × 0.31

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.794, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	10823, 2418, 1922
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.138, 1.04
No. of reflections	2418
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS2013 and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1036743

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018017450/is5506sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018017450/is5506Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018017450/is5506Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-3-(4-Fluorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀FNO₃	F(000) = 560
M_r = 271.24	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8860 (5) Å	Cell parameters from 4607 reflections
b = 13.2324 (16) Å	θ = 2.3–30.4°
c = 24.199 (3) Å	µ = 0.11 mm⁻¹
β = 91.963 (2)°	T = 296 K
V = 1243.6 (3) Å³	Block, yellow
Z = 4	0.49 × 0.35 × 0.31 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	2418 independent reflections
Radiation source: fine-focus sealed tube	1922 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→4
T_min = 0.794, T_max = 0.926	k = −16→15
10823 measured reflections	l = −29→29

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.072P)² + 0.3042P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2418 reflections	Δρ_max = 0.21 e Å⁻³
181 parameters	Δρ_min = −0.17 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
F1	0.7362 (4)	−0.01394 (9)	0.57883 (5)	0.0899 (5)
O1	−0.1032 (4)	0.85915 (12)	0.77829 (6)	0.0784 (5)
O2	0.0898 (6)	0.97163 (12)	0.72386 (8)	0.1026 (7)
O3	0.7296 (4)	0.61266 (9)	0.55381 (5)	0.0665 (4)
N1	0.0476 (4)	0.88363 (12)	0.73723 (6)	0.0578 (4)
C1	0.3037 (4)	0.63109 (12)	0.68456 (6)	0.0460 (4)
H1A	0.2995	0.5638	0.6955	0.055*
C2	0.1758 (4)	0.70499 (13)	0.71878 (6)	0.0479 (4)
H2A	0.0857	0.6880	0.7527	0.057*
C3	0.1848 (4)	0.80391 (12)	0.70162 (6)	0.0443 (4)
C4	0.3144 (5)	0.83206 (12)	0.65149 (7)	0.0502 (4)
H4A	0.3157	0.8995	0.6407	0.060*
C5	0.4418 (4)	0.75795 (12)	0.61790 (6)	0.0474 (4)
H5A	0.5311	0.7757	0.5841	0.057*
C6	0.4388 (4)	0.65682 (11)	0.63385 (6)	0.0397 (4)
C7	0.5886 (4)	0.58109 (12)	0.59466 (6)	0.0437 (4)
C8	0.5671 (4)	0.47246 (12)	0.60636 (7)	0.0465 (4)
H8A	0.4609	0.4501	0.6380	0.056*
C9	0.6995 (4)	0.40594 (13)	0.57171 (6)	0.0461 (4)
H9A	0.8020	0.4332	0.5409	0.055*
C10	0.7052 (4)	0.29630 (12)	0.57557 (6)	0.0441 (4)
C11	0.8374 (4)	0.24150 (13)	0.53176 (7)	0.0498 (4)
H11A	0.9211	0.2760	0.5015	0.060*
C12	0.8463 (5)	0.13763 (14)	0.53240 (8)	0.0573 (5)
H12A	0.9314	0.1015	0.5029	0.069*
C13	0.7264 (5)	0.08894 (13)	0.57778 (7)	0.0571 (5)
C14	0.5966 (5)	0.13871 (13)	0.62234 (7)	0.0571 (5)
H14A	0.5188	0.1032	0.6526	0.069*
C15	0.5851 (4)	0.24251 (13)	0.62076 (7)	0.0504 (4)
H15A	0.4958	0.2776	0.6503	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1376 (12)	0.0406 (6)	0.0943 (9)	0.0055 (6)	0.0442 (9)	0.0029 (6)
O1	0.1010 (11)	0.0756 (10)	0.0608 (8)	0.0045 (8)	0.0352 (8)	−0.0084 (7)
O2	0.1626 (18)	0.0471 (9)	0.1018 (12)	0.0065 (9)	0.0579 (12)	−0.0095 (8)
O3	0.0962 (10)	0.0503 (7)	0.0550 (7)	−0.0027 (7)	0.0350 (7)	0.0017 (6)
N1	0.0665 (10)	0.0540 (10)	0.0534 (9)	0.0024 (7)	0.0107 (7)	−0.0086 (7)
C1	0.0552 (10)	0.0401 (9)	0.0430 (8)	−0.0028 (7)	0.0065 (7)	0.0049 (6)
C2	0.0546 (9)	0.0502 (10)	0.0395 (8)	−0.0036 (7)	0.0103 (7)	0.0030 (7)
C3	0.0465 (9)	0.0449 (9)	0.0417 (8)	−0.0009 (7)	0.0050 (7)	−0.0049 (7)
C4	0.0622 (10)	0.0374 (8)	0.0515 (9)	−0.0012 (7)	0.0107 (8)	0.0028 (7)
C5	0.0580 (10)	0.0443 (9)	0.0406 (8)	−0.0030 (7)	0.0110 (7)	0.0055 (7)
C6	0.0409 (8)	0.0398 (8)	0.0386 (8)	−0.0025 (6)	0.0027 (6)	0.0008 (6)
C7	0.0469 (9)	0.0449 (9)	0.0397 (8)	−0.0027 (7)	0.0056 (6)	0.0004 (6)
C8	0.0502 (9)	0.0438 (9)	0.0459 (8)	−0.0013 (7)	0.0098 (7)	0.0018 (7)
C9	0.0475 (9)	0.0464 (9)	0.0447 (8)	−0.0016 (7)	0.0061 (7)	0.0018 (7)
C10	0.0424 (8)	0.0450 (9)	0.0450 (8)	0.0008 (7)	0.0056 (7)	−0.0011 (7)
C11	0.0562 (10)	0.0493 (10)	0.0449 (9)	0.0016 (7)	0.0155 (7)	0.0020 (7)
C12	0.0689 (11)	0.0505 (10)	0.0538 (10)	0.0072 (8)	0.0206 (9)	−0.0059 (8)
C13	0.0689 (12)	0.0398 (9)	0.0634 (11)	0.0028 (8)	0.0151 (9)	0.0014 (8)
C14	0.0711 (12)	0.0503 (10)	0.0512 (10)	−0.0003 (8)	0.0194 (8)	0.0073 (8)
C15	0.0586 (10)	0.0494 (10)	0.0443 (9)	0.0032 (7)	0.0147 (7)	−0.0024 (7)

Geometric parameters (Å, º) top

F1—C13	1.362 (2)	C7—C8	1.468 (2)
O1—N1	1.2147 (19)	C8—C9	1.331 (2)
O2—N1	1.221 (2)	C8—H8A	0.9300
O3—C7	1.2204 (19)	C9—C10	1.454 (2)
N1—C3	1.473 (2)	C9—H9A	0.9300
C1—C2	1.385 (2)	C10—C11	1.397 (2)
C1—C6	1.393 (2)	C10—C15	1.398 (2)
C1—H1A	0.9300	C11—C12	1.375 (2)
C2—C3	1.374 (2)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.369 (3)
C3—C4	1.381 (2)	C12—H12A	0.9300
C4—C5	1.377 (2)	C13—C14	1.374 (2)
C4—H4A	0.9300	C14—C15	1.375 (2)
C5—C6	1.393 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.510 (2)

O1—N1—O2	122.95 (16)	C9—C8—C7	120.02 (14)
O1—N1—C3	118.80 (16)	C9—C8—H8A	120.0
O2—N1—C3	118.24 (15)	C7—C8—H8A	120.0
C2—C1—C6	120.53 (14)	C8—C9—C10	128.67 (15)
C2—C1—H1A	119.7	C8—C9—H9A	115.7
C6—C1—H1A	119.7	C10—C9—H9A	115.7
C3—C2—C1	118.60 (14)	C11—C10—C15	118.08 (15)
C3—C2—H2A	120.7	C11—C10—C9	118.33 (14)
C1—C2—H2A	120.7	C15—C10—C9	123.59 (14)
C2—C3—C4	122.43 (15)	C12—C11—C10	121.34 (15)
C2—C3—N1	119.47 (14)	C12—C11—H11A	119.3
C4—C3—N1	118.09 (15)	C10—C11—H11A	119.3
C5—C4—C3	118.43 (15)	C13—C12—C11	118.06 (16)
C5—C4—H4A	120.8	C13—C12—H12A	121.0
C3—C4—H4A	120.8	C11—C12—H12A	121.0
C4—C5—C6	120.95 (14)	F1—C13—C12	118.38 (16)
C4—C5—H5A	119.5	F1—C13—C14	118.37 (16)
C6—C5—H5A	119.5	C12—C13—C14	123.25 (17)
C5—C6—C1	119.06 (14)	C13—C14—C15	118.00 (15)
C5—C6—C7	117.17 (13)	C13—C14—H14A	121.0
C1—C6—C7	123.78 (14)	C15—C14—H14A	121.0
O3—C7—C8	121.43 (15)	C14—C15—C10	121.26 (15)
O3—C7—C6	118.36 (14)	C14—C15—H15A	119.4
C8—C7—C6	120.20 (13)	C10—C15—H15A	119.4

C6—C1—C2—C3	0.0 (3)	C1—C6—C7—C8	6.1 (2)
C1—C2—C3—C4	0.4 (3)	O3—C7—C8—C9	−0.8 (3)
C1—C2—C3—N1	179.54 (15)	C6—C7—C8—C9	−179.99 (15)
O1—N1—C3—C2	−7.6 (2)	C7—C8—C9—C10	−179.96 (15)
O2—N1—C3—C2	172.67 (18)	C8—C9—C10—C11	175.31 (17)
O1—N1—C3—C4	171.54 (17)	C8—C9—C10—C15	−4.6 (3)
O2—N1—C3—C4	−8.2 (3)	C15—C10—C11—C12	0.8 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C10—C11—C12	−179.15 (16)
N1—C3—C4—C5	−179.74 (15)	C10—C11—C12—C13	−1.0 (3)
C3—C4—C5—C6	0.3 (3)	C11—C12—C13—F1	−179.66 (17)
C4—C5—C6—C1	0.1 (3)	C11—C12—C13—C14	0.4 (3)
C4—C5—C6—C7	−179.16 (15)	F1—C13—C14—C15	−179.50 (17)
C2—C1—C6—C5	−0.3 (2)	C12—C13—C14—C15	0.5 (3)
C2—C1—C6—C7	178.91 (15)	C13—C14—C15—C10	−0.7 (3)
C5—C6—C7—O3	6.1 (2)	C11—C10—C15—C14	0.1 (3)
C1—C6—C7—O3	−173.10 (16)	C9—C10—C15—C14	−179.98 (16)
C5—C6—C7—C8	−174.65 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···F1ⁱ	0.93	2.53	3.183 (2)	128
C11—H11A···O3ⁱⁱ	0.93	2.43	3.329 (2)	161
C15—H15A···O1ⁱⁱⁱ	0.93	2.58	3.489 (2)	166

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1; (iii) −x, y−1/2, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: F-8816-2012.

§Thomson Reuters ResearcherID: A-5525-2009.

Funding information

QAW thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Individual Grant (1001/PFIZIK/8011080). HCK thanks the Malaysian Government for a MyBrain15 scholarship.

References

Boulanger, B. & Zyss, J. (2006). International Tables for Crystallography, Vol. D, ch. 1.7, 178–219. Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chandra Shekhara Shetty, T., Chidan Kumar, C. S., Gagan Patel, K. N., Chia, T. S., Dharmaprakash, S. M., Ramasami, P., Umar, Y., Chandraju, S. & Quah, C. K. (2017). J. Mol. Struct. 1143, 306–317. Web of Science CrossRef Google Scholar
Ekbote, A., Patil, P. S., Maidur, S. R., Chia, T. S. & Quah, C. K. (2017). Dyes Pigments, 139, 720–729. CrossRef Google Scholar
Fun, H.-K., Loh, W.-S., Sarojini, B. K., Khaleel, V. M. & Narayana, B. (2011). Acta Cryst. E67, o2651–o2652. Web of Science CrossRef IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Jing, L.-H. (2009a). Acta Cryst. E65, o2510. CrossRef IUCr Journals Google Scholar
Jing, L.-H. (2009b). Acta Cryst. E65, o2515. CrossRef IUCr Journals Google Scholar
Kwong, H. C., Rakesh, M. S., Chidan Kumar, C. S., Maidur, S. R., Patil, P. S., Quah, C. K., Win, Y.-F., Parlak, C. & Chandraju, S. (2018). Z. Kristallogr. Cryst. Mater. 233, 349–360. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Prabhu, A. N., Jayarama, A., Subrahmanya Bhat, K., Manjunatha, K. B., Umesh, G. & Upadhyaya, V. (2013). Indian J. Mater. Sci. 2013, 1–5. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392. Web of Science CrossRef CAS Google Scholar
Spackman, M. A., McKinnon, J. J. & Jayatilaka, D. (2008). CrystEngComm, 10, 377–388. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.