Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-eth-oxy-quinoline-4-carboxyl-ate.

In the title quinoline derivative, C14H14ClNO3, there is an intra-molecular C-H⋯O hydrogen bond forming an S(6) graph-set motif. The mol-ecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-eth-oxy-quinoline mean plane. In the crystal, offset π-π inter-actions with a centroid-to-centroid distance of 3.4731 (14) Å link inversion-related mol-ecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H⋯H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

Chemical context

Quinoline derivatives represent an important class of bioactive heterocyclic compounds in the field of pharmaceuticals (Chu et al., 2019 ▸). Quinoline derivatives possess various pharmacological properties such as anti­bacterial (Panda et al., 2015 ▸), anti-HCV (Cannalire et al., 2016 ▸), anti­viral (Sekgota et al., 2017 ▸), anti­cancer (Tang et al., 2018 ▸), anti­malarial (van Heerden et al., 2012 ▸), anti­leishmanial (Palit et al., 2009 ▸), anti­tubecular (Xu et al., 2017 ▸), anti-inflammatory (de Santos et al., 2015 ▸) and anti-Alzheimer’s (Bolognesi et al., 2007 ▸) activities. The present work is a continuation of our research work devoted to the synthesis and crystal structure of heterocyclic derivatives (Bouzian et al., 2018 ▸; Chkirate et al. 2019a ▸,b ▸). As part of our studies in this area, we prepared the title compound by reacting ethyl 6-chloro-2-oxo-1,2-di­hydro­quinoline-4-carboxyl­ate with bromo­ethane in the presence of a catalytic qu­antity of tetra-n-butyl­ammonium bromide. We report herein on its crystal and mol­ecular structures along with the Hirshfeld surface analysis.

Structural commentary

The mol­ecular structure of the title compound is shown in Fig. 1 ▸ a. The mol­ecule consists of a quinoline fused-ring system (N1/C1–C9) with meth­oxy­ethane (O2/C10/C11), ethyl acetate (O3/O4/C13/C14) and a chlorine atom (Cl1) substituents. The intra­molecular C5—H5A⋯O3 hydrogen bond (Table 1 ▸) forms an S(6) graph-set motif, stabilizing the mol­ecular structure and preventing free rotation between the 6-chloro­quinoline ring (Cl1/N1/C1–C9) and the ethyl acetate (O3/O4/C12–C14) moiety. Additionally, the presence of this intra­molecular C—H⋯O inter­action leads to an essentially planar mol­ecular structure (Fig. 1 ▸ b), where the ethyl acetate (O3/O4/C12–C14) mean plane is twisted slightly at a dihedral angle of 5.02 (3)° with respect to the mean plane of the ethyl 6-chloro-2-eth­oxy­quinoline (Cl1/O2/C1–C11) moiety. This essentially planar mol­ecular structure may be considered an important binding mode that can enhance biological activity (Bierbach et al., 1999 ▸).

Figure 1

(a) The mol­ecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level. The dashed line represents the intra­molecular C—H⋯O inter­action (Table 1 ▸). (b) The essentially planar structure of the title compound.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3	0.93	2.24	2.872 (4)	125

Supra­molecular features

In the crystal, mol­ecules lie in a plane parallel to the (10) crystallographic plane (Fig. 2 ▸ a). They are linked by offset π–π inter­actions (Fig. 2 ▸ b) involving inversion-related pyridine rings. These inter­actions link the mol­ecules into columns up the c-axis direction with a centroid-to-centroid (Cg⋯Cg i) distance of 3.4731 (14) Å [Cg is centroid of the N1/C1–C4/C9 ring, inter­planar distance = 3.397 (1) Å, offset = 0.722 Å; symmetry code (i): −x + 1, −y, −z + 1].

Figure 2

(a) A partial view along the c axis of the crystal packing of the title compound. (b) A view along the c axis of the crystal packing of the title compound.

Hirshfeld surface analysis

The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) were performed with CrystalExplorer17 (Turner et al., 2017 ▸). Inter­nal and external (d i and d e) contact distances from the Hirshfeld surface to the nearest atom inside and outside enables the analysis of the inter­molecular inter­actions through the mapping of d norm. The Hirshfeld surfaces (HS) mapped over the electrostatic potential (−0.0534 to 0.0319 atomic units) and d norm (−0.0210 to 1.4779 arbitrary units) are shown in Fig. 3 ▸ a and 3b. The red spots on the Hirshfeld surface indicate inter­actions involved in H⋯O contacts. The π–π stacking is confirmed by the small blue regions surrounding bright red spots in the aromatic ring in Fig. 3 ▸ c, the Hirshfeld surface mapped over the shape-index, and by the flat regions around the aromatic regions in Fig. 3 ▸ d, the Hirshfeld surface mapped over the curvedness.

Figure 3

Hirshfeld surface of the title compound mapped over: (a) electrostatic potential, (b) d norm, (c) shape-index and (d) curvedness.

There are no significant classical inter­molecular contacts present in the crystal according to the analysis of the crystal structure using PLATON (Spek, 2009 ▸). However, from the Hirshfeld surface analysis and the two-dimensional fingerprint plots it can be seen that H⋯H, C⋯H, Cl⋯H and O⋯H contacts (Fig. 4 ▸) contribute to the cohesion of the crystal structure. The two-dimensional fingerprint plots are given in Fig. 5 ▸. The two-dimensional fingerprint of the (d, d) points associated with the hydrogen atoms is shown in Fig. 5 ▸ b. It is characterized by an end point that points to the origin, indicating the presence of the H⋯H contacts that contribution 50.8%. The Cl⋯H/H⋯Cl contacts between the chlorine atoms inside the Hirshfeld surface and the hydrogen atoms outside the surface and vice versa contribute 16.0% (Fig. 5 ▸ c). The O⋯H/H⋯O (10.3%) plot shows two symmetrical wings on the left and right sides (Fig. 5 ▸ d). The C⋯C contacts contribute 7.9% (Fig. 5 ▸ e), the C⋯H/H⋯C contacts contribute 5.3% (Fig. 5 ▸ e), followed by the C⋯O contacts at 3.7% (Fig. 5 ▸ g) and the C⋯N contacts at 3.3% (Fig. 3 ▸ h).

Figure 4

A view of the inter­molecular contacts (dashed lines) in the crystal of the title compound. They are all longer by 0.02 Å than the sum of the van der Waals radii of the individual atoms.

Figure 5

(a) The two-dimensional fingerprint plot of the title compound, and the fingerprint plots delineated into: (b) H⋯H (50.8%), (c) Cl⋯H/H⋯Cl (16.0%), (d) O⋯H/H⋯O (10.3%), (e) C⋯C (7.9%), (f) C⋯H/H⋯C (5.3%), (g) C⋯O (3.7%) and (h) C⋯N (3.3%) contacts.

DFT study

The electrostatic potential surface (ESP) was also calculated using DFT methods at the B3LYP/6-311+G(d,p) level of theory using the Gaussian 09 package (Frisch et al., 2009 ▸). The negative region on the electrostatic potential appears in red and corresponds to hydrogen-bond acceptors, while the positive region of electrostatic potential appears in blue and corresponds to hydrogen-bond donors (Fig. 6 ▸).

Figure 6

EPS of the title compound obtained at the B3LYP/6–31+G(d,p) level of theory.

Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, last update May 2019; Groom et al., 2016 ▸) for the 6-chloro­quinoline skeleton gave 100 hits, including 6-chloro­quinoline itself (CSD refcode CLQUIN; Merlino, 1968 ▸). Only a limited number of these structures are similar to the title compound. There are no compounds with a 6-chloro-2-eth­oxy­quinoline moiety and only four compounds with a 6-chloro-2-meth­oxy­quinoline moiety. These include, 1-{6-chloro-2-[(2-chloro-8-methyl­quinolin-3-yl)meth­oxy]-4-phen­yl­quinolin-3-yl}ethanone (DUVJEK; Khan et al., 2010a ▸), ethyl 6-chloro-2-[(2-chloro-7,8-di­methyl­quinolin-3-yl)meth­oxy]-4-phenyl­quinoline-3-carboxyl­ate (KUVFEN; Khan et al., 2010b ▸), 1-{6-chloro-2-[(2-chloro­quinolin-3-yl)meth­oxy]-4-phenyl­quinolin-3-yl}ethanone (YUQTAG; Khan et al., 2010c ▸), and 1-{6-chloro-2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]-4-phenyl­quinolin-3-yl}ethanone (YUQVIQ; Khan et al., 2010d ▸). Two other relevant compounds with an ethyl carboxyl­ate substituent include ethyl 2,6-di­chloro-4-phenyl­quinoline-3-carboxyl­ate (DUKKUQ; Roopan et al., 2009 ▸) and ethyl 6-chloro-2-methyl-4-phenyl­quinoline-3-carboxyl­ate (DUKJEZ; Subashini et al., 2009 ▸). In the crystals of all of the above mentioned compounds, mol­ecules are linked by offset π–π inter­actions involving inversion-related quinoline units.

Synthesis and crystallization

A solution of 0.5 g (1.99 mmol) of ethyl 6-chloro-2-oxo-1,2-di­hydro­quinoline-4-carboxyl­ate in 25 ml of DMF was mixed with 0.3 ml (3.98 mmol) of bromo­ethane, 0.55 g (3.98 mmol) of K2CO3 and 0.06 g (0.199 mmol) of tetra-n-butyl­ammonium bromide (TBAB). The reaction mixture was stirred at room temperature in DMF for 24 h. After removal of salts by filtration, the DMF was evaporated under reduced pressure and the residue obtained was dissolved in di­chloro­methane·The organic phase was dried over Na2SO4 then concentrated in vacuo. The resulting mixture was chromatographed on a silica gel column [eluent: ethyl acetate/hexane (1:9 v/v)]. Colourless crystals were obtained when the solvent was allowed to evaporate (yield: 32%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were positioned geometrically and refined using a riding model: C—H = 0.93-0.97 Å with U iso(H) = 1.5U eq(C-meth­yl) and 1.2U eq(C) for other H atoms. A rotating group model was applied to the methyl groups.

Table 2

Experimental details

Crystal data
Chemical formula	C14H14ClNO3
M r	279.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	14.2634 (7), 16.0124 (7), 13.7732 (6)
β (°)	117.748 (2)
V (Å3)	2783.9 (2)
Z	8
Radiation type	Mo Kα
μ (mm−1)	0.28
Crystal size (mm)	0.50 × 0.47 × 0.37
Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009 ▸)
No. of measured, independent and observed [I > 2σ(I)] reflections	45458, 3190, 2228
R int	0.029
(sin θ/λ)max (Å−1)	0.650
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.058, 0.203, 1.10
No. of reflections	3190
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.30, −0.32

Computer programs: APEX2 and SAINT (Bruker, 2009 ▸), SHELXS and SHELXTL (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸), Mercury (Macrae et al., 2008 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989019007473/mw2143sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019007473/mw2143Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989019007473/mw2143Isup3.cml

CCDC reference: 1890687

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

C14H14ClNO3	F(000) = 1168
Mr = 279.71	Dx = 1.335 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.2634 (7) Å	Cell parameters from 9928 reflections
b = 16.0124 (7) Å	θ = 2.5–24.5°
c = 13.7732 (6) Å	µ = 0.28 mm−1
β = 117.748 (2)°	T = 296 K
V = 2783.9 (2) Å3	Block, colourless
Z = 8	0.50 × 0.47 × 0.37 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	2228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
	k = −20→20
45458 measured reflections	l = −17→17
3190 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0854P)2 + 2.5795P] where P = (Fo2 + 2Fc2)/3
3190 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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

	x	y	z	Uiso*/Ueq
N1	0.56133 (16)	0.10176 (12)	0.41064 (15)	0.0584 (5)
Cl1	0.10792 (6)	0.02217 (6)	0.16402 (10)	0.1199 (5)
O2	0.73447 (14)	0.05835 (11)	0.51005 (15)	0.0707 (5)
O3	0.39144 (18)	−0.18904 (14)	0.3085 (2)	0.1148 (9)
O4	0.55981 (16)	−0.20506 (11)	0.42458 (19)	0.0872 (6)
C1	0.63047 (19)	0.04194 (15)	0.44989 (19)	0.0572 (6)
C2	0.60502 (19)	−0.04443 (15)	0.43555 (19)	0.0577 (5)
H2A	0.6582	−0.0845	0.4655	0.069*
C3	0.50216 (18)	−0.06779 (14)	0.37760 (18)	0.0547 (5)
C4	0.42215 (18)	−0.00513 (14)	0.33217 (17)	0.0542 (5)
C5	0.3122 (2)	−0.02093 (17)	0.2719 (2)	0.0645 (6)
H5A	0.2876	−0.0756	0.2569	0.077*
C6	0.2427 (2)	0.04352 (19)	0.2358 (2)	0.0741 (7)
C7	0.2757 (2)	0.12657 (19)	0.2548 (2)	0.0759 (7)
H7A	0.2264	0.1697	0.2294	0.091*
C8	0.3812 (2)	0.14362 (16)	0.3112 (2)	0.0682 (7)
H8A	0.4037	0.1989	0.3233	0.082*
C9	0.45660 (19)	0.07928 (14)	0.35138 (18)	0.0554 (5)
C10	0.7649 (2)	0.14510 (18)	0.5310 (2)	0.0761 (8)
H10A	0.7270	0.1724	0.5651	0.091*
H10B	0.7486	0.1737	0.4629	0.091*
C11	0.8808 (3)	0.1471 (2)	0.6056 (4)	0.1162 (14)
H11A	0.9045	0.2041	0.6195	0.174*
H11B	0.9172	0.1183	0.5720	0.174*
H11C	0.8957	0.1203	0.6736	0.174*
C12	0.4759 (2)	−0.15957 (16)	0.3647 (2)	0.0649 (6)
C13	0.5438 (3)	−0.29493 (18)	0.4194 (4)	0.1060 (12)
H13A	0.4951	−0.3092	0.4477	0.127*
H13B	0.5133	−0.3135	0.3437	0.127*
C14	0.6421 (3)	−0.3350 (2)	0.4822 (6)	0.181 (3)
H14A	0.6739	−0.3139	0.5559	0.271*
H14B	0.6882	−0.3243	0.4503	0.271*
H14C	0.6311	−0.3941	0.4830	0.271*

	U11	U22	U33	U12	U13	U23
N1	0.0598 (11)	0.0493 (10)	0.0607 (11)	−0.0024 (8)	0.0234 (9)	0.0043 (8)
Cl1	0.0539 (4)	0.0945 (7)	0.1717 (10)	0.0034 (4)	0.0193 (5)	0.0156 (6)
O2	0.0549 (10)	0.0585 (10)	0.0825 (11)	−0.0052 (8)	0.0183 (9)	0.0045 (8)
O3	0.0763 (14)	0.0587 (12)	0.152 (2)	−0.0105 (10)	0.0054 (14)	−0.0116 (13)
O4	0.0709 (12)	0.0473 (10)	0.1220 (16)	0.0002 (8)	0.0268 (11)	0.0063 (10)
C1	0.0556 (13)	0.0541 (12)	0.0576 (12)	−0.0060 (10)	0.0227 (10)	0.0019 (10)
C2	0.0561 (13)	0.0517 (12)	0.0624 (13)	0.0011 (10)	0.0251 (11)	0.0036 (10)
C3	0.0592 (13)	0.0486 (12)	0.0561 (12)	−0.0037 (10)	0.0267 (10)	−0.0002 (9)
C4	0.0579 (13)	0.0540 (12)	0.0509 (11)	−0.0003 (10)	0.0255 (10)	0.0019 (9)
C5	0.0572 (14)	0.0617 (14)	0.0696 (15)	−0.0041 (11)	0.0253 (12)	−0.0001 (11)
C6	0.0533 (14)	0.0739 (17)	0.0837 (18)	0.0037 (12)	0.0223 (13)	0.0067 (14)
C7	0.0659 (16)	0.0661 (16)	0.0890 (19)	0.0116 (13)	0.0303 (14)	0.0087 (14)
C8	0.0661 (15)	0.0539 (13)	0.0782 (16)	0.0041 (11)	0.0283 (13)	0.0067 (12)
C9	0.0586 (13)	0.0519 (12)	0.0543 (12)	−0.0009 (10)	0.0251 (10)	0.0032 (9)
C10	0.0634 (15)	0.0614 (15)	0.0877 (18)	−0.0145 (12)	0.0218 (14)	−0.0014 (13)
C11	0.068 (2)	0.097 (3)	0.140 (3)	−0.0215 (18)	0.012 (2)	0.009 (2)
C12	0.0628 (15)	0.0534 (13)	0.0731 (15)	−0.0026 (11)	0.0272 (12)	−0.0030 (11)
C13	0.100 (2)	0.0447 (15)	0.152 (3)	−0.0038 (15)	0.041 (2)	0.0042 (17)
C14	0.084 (3)	0.057 (2)	0.328 (8)	0.0106 (18)	0.034 (4)	0.033 (3)

N1—C1	1.298 (3)	C6—C7	1.394 (4)
N1—C9	1.375 (3)	C7—C8	1.361 (4)
Cl1—C6	1.737 (3)	C7—H7A	0.9300
O2—C1	1.346 (3)	C8—C9	1.404 (3)
O2—C10	1.444 (3)	C8—H8A	0.9300
O3—C12	1.186 (3)	C10—C11	1.486 (4)
O4—C12	1.313 (3)	C10—H10A	0.9700
O4—C13	1.454 (3)	C10—H10B	0.9700
C1—C2	1.420 (3)	C11—H11A	0.9600
C2—C3	1.356 (3)	C11—H11B	0.9600
C2—H2A	0.9300	C11—H11C	0.9600
C3—C4	1.427 (3)	C13—C14	1.413 (5)
C3—C12	1.506 (3)	C13—H13A	0.9700
C4—C5	1.415 (3)	C13—H13B	0.9700
C4—C9	1.420 (3)	C14—H14A	0.9600
C5—C6	1.355 (4)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600
C1—N1—C9	117.3 (2)	C8—C9—C4	119.3 (2)
C1—O2—C10	117.0 (2)	O2—C10—C11	107.1 (2)
C12—O4—C13	116.2 (2)	O2—C10—H10A	110.3
N1—C1—O2	121.2 (2)	C11—C10—H10A	110.3
N1—C1—C2	124.4 (2)	O2—C10—H10B	110.3
O2—C1—C2	114.4 (2)	C11—C10—H10B	110.3
C3—C2—C1	119.1 (2)	H10A—C10—H10B	108.6
C3—C2—H2A	120.4	C10—C11—H11A	109.5
C1—C2—H2A	120.4	C10—C11—H11B	109.5
C2—C3—C4	119.3 (2)	H11A—C11—H11B	109.5
C2—C3—C12	118.7 (2)	C10—C11—H11C	109.5
C4—C3—C12	122.0 (2)	H11A—C11—H11C	109.5
C5—C4—C9	118.2 (2)	H11B—C11—H11C	109.5
C5—C4—C3	125.0 (2)	O3—C12—O4	122.8 (3)
C9—C4—C3	116.8 (2)	O3—C12—C3	125.9 (3)
C6—C5—C4	120.1 (2)	O4—C12—C3	111.3 (2)
C6—C5—H5A	120.0	C14—C13—O4	109.3 (3)
C4—C5—H5A	120.0	C14—C13—H13A	109.8
C5—C6—C7	122.1 (3)	O4—C13—H13A	109.8
C5—C6—Cl1	119.0 (2)	C14—C13—H13B	109.8
C7—C6—Cl1	118.8 (2)	O4—C13—H13B	109.8
C8—C7—C6	119.0 (3)	H13A—C13—H13B	108.3
C8—C7—H7A	120.5	C13—C14—H14A	109.5
C6—C7—H7A	120.5	C13—C14—H14B	109.5
C7—C8—C9	121.2 (3)	H14A—C14—H14B	109.5
C7—C8—H8A	119.4	C13—C14—H14C	109.5
C9—C8—H8A	119.4	H14A—C14—H14C	109.5
N1—C9—C8	117.6 (2)	H14B—C14—H14C	109.5
N1—C9—C4	123.1 (2)
C9—N1—C1—O2	−179.1 (2)	C6—C7—C8—C9	−0.8 (4)
C9—N1—C1—C2	0.1 (3)	C1—N1—C9—C8	178.3 (2)
C10—O2—C1—N1	1.5 (3)	C1—N1—C9—C4	0.1 (3)
C10—O2—C1—C2	−177.7 (2)	C7—C8—C9—N1	−177.9 (2)
N1—C1—C2—C3	−0.2 (4)	C7—C8—C9—C4	0.4 (4)
O2—C1—C2—C3	179.0 (2)	C5—C4—C9—N1	178.8 (2)
C1—C2—C3—C4	0.2 (3)	C3—C4—C9—N1	−0.1 (3)
C1—C2—C3—C12	−178.9 (2)	C5—C4—C9—C8	0.6 (3)
C2—C3—C4—C5	−178.9 (2)	C3—C4—C9—C8	−178.3 (2)
C12—C3—C4—C5	0.2 (4)	C1—O2—C10—C11	175.5 (3)
C2—C3—C4—C9	−0.1 (3)	C13—O4—C12—O3	−0.4 (5)
C12—C3—C4—C9	179.0 (2)	C13—O4—C12—C3	179.5 (3)
C9—C4—C5—C6	−1.2 (4)	C2—C3—C12—O3	−172.8 (3)
C3—C4—C5—C6	177.5 (2)	C4—C3—C12—O3	8.1 (4)
C4—C5—C6—C7	0.9 (4)	C2—C3—C12—O4	7.3 (3)
C4—C5—C6—Cl1	−178.9 (2)	C4—C3—C12—O4	−171.8 (2)
C5—C6—C7—C8	0.1 (5)	C12—O4—C13—C14	176.2 (4)
Cl1—C6—C7—C8	179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3	0.93	2.24	2.872 (4)	125