trans-3-(2-Chloro-3-quinol­yl)-1-phenyl-2,3-epoxy­propan-1-one

Boulcina, R.; Bouacida, S.; Roisnel, T.; Debache, A.

doi:10.1107/S1600536807039335

trans-3-(2-Chloro-3-quinolyl)-1-phenyl-2,3-epoxypropan-1-one

R. Boulcina, S. Bouacida, T. Roisnel and A. Debache

In the title molecule, C₁₈H₁₂ClNO₂, a quinolyl moiety is linked to a functionalized epoxide system in a trans configuration. The epoxide ring forms dihedral angles of 62.27 (2) and 79.82 (2)° with the 2-chloropyridine ring of the 2-chloroquinolyl group and the phenyl ring, respectively. The mean plane of the atoms of the quinolyl ring system forms a dihedral angle of 35.03 (1)° with the phenyl ring. The crystal structure can be described as layers in which epoxide rings lie parallel to the (10 $\overline{1}$ ) plane. The packing is stabilized by weak C—H

O and C—H

N intra- and intermolecular hydrogen bonds, resulting in the formation of a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039335/lh2468sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039335/lh2468Isup2.hkl Contains datablock I

CCDC reference: 660280

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.109
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C11    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C12    = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Quinolines have been extensively investigated by organic chemsits due to their association with biological activities like antibacterial (Ibrahim et al., 1991), antifungal (Moiseer et al., 1988) and antifilarial (Srivastava et al., 1991) activities. In addition, naturally occurring epoxides are associated with various industrial, mechanistic and biological activities (Pearson & Ong, 1981). New and less toxic antiviral agents are in great demand due to typical viral infections (Kidwai et al., 1996). We thought it worthwhile to synthesize new quinoline substituted epoxides and screen them for their antiviral activity against EMC virus (Rivers & Horsfall, 1959). The antiviral activity of quinoline substituted epoxides were tested against Encephalomyocarditis Virus (EMCV) (Lennette, 1964) and cytotoxic assays of these compounds were also evaluated (Sidwell & Hofmann, 1971). As a result of their importance in synthesis, the preparation of epoxides has been of a considerable interest and many methods have been developed to date. An alternative and complementary approach utilizes aldehydes. The advantage of this approach is that potentially hazardous oxidizing agents are not required. Epoxides bearing electron-withdrawing groups are very important synthetic intermediates because of their rich and useful functionality (Adam et al., 2001; De Vos et al., 1998). These compounds have been most commonly synthesized by the Darzens reaction (Maryanoff et al., 1994). This involves the initial addition of an α-halo enolate to a carbonyl compound, followed by ring-closure of the resulting alkoxide. In continuation of our research program directed towards the preparation of new quinoline derivatives (Menasra et al., 2005; Moussaoui et al., 2002; Rezig et al., 2000; Kedjadja et al., 2004), we present here our results concerning the epoxidation of 2-chloro-3-formylquinoline.

In this study, we have synthesized trans- 2,3-epoxy-3-(2'-chloroquinolyl)-1-phenylpropan-1-one and determined its crystal structure.

The molecular geometry and the atom-numbering scheme are shown in Fig. 1. The title molecule contains an epoxide group linked to a chloroquinolyl moiety and benzoyl group with 2, 3-trans configuration relationship.

The two rings of quinolyl group form a dihedral angle of 1.22 (1)° between them. The epoxide ring forms dihedral angles of 62.27 (2)° and 79.82 (2)° with the 2-chloropyridine ring of the 2-chloroquinolyl group and phenyl rings respectively. The mean plane of the atoms of the quinolyl ring fused rings system forms a dihedral angle of 35.03 (1)° with phenyl ring. The crystal structure can be described as layers in which the epoxide rings are parallel to (10–1) plane (Fig. 2).

The crystal packing is stabilized by C–H···O and C–H···N intra and intermolecular hydrogen bonds, resulting in the formation of three dimensional network (Fig. 3).

Related literature top

For related literature regarding synthetic procedures, see: Kidwai et al. (1996); Adam et al. (2001); De Vos et al. (1998) For applications, see: Ibrahim et al. (1991); Srivastava et al. (1991); Moiseer et al. (1988). For other related literature, see: Kedjadja et al. (2004); Lennette (1964); Maryanoff et al. (1994); Menasra et al. (2005); Moussaoui et al. (2002); Pearson & Ong (1981); Rezig et al. (2000); Rivers & Horsfall (1959); Sidwell & Hofmann (1971).

Experimental top

To a solution of 2-chloro-3-formylquinoline (1 mmol) in toluene (15 mL) was added 1 mmol of 2-bromoacetophenone, and the mixture was cooled to 273 K. An aqueous solution of KOH 30% (2.5 ml) was added dropwise over a period of 2 minutes. This mixture was stired for 24 h at room temperature. The reaction was worked up by adding 15 ml of cold water and 15 ml of saturated aqueous ammonium chloride. This solution was extracted twice with methylene chloride (25 ml) and the combined organic layers were washed twice with cold water (10 ml), saturated aqueous ammonium chloride (10 ml) and dried over MgSO₄ then concentrated in vacuo. The obtained residue was purified by a column chromatograpy (SiO₂, methylene chloride) to furnish the pure product.

Structure description top

In this study, we have synthesized trans- 2,3-epoxy-3-(2'-chloroquinolyl)-1-phenylpropan-1-one and determined its crystal structure.

The crystal packing is stabilized by C–H···O and C–H···N intra and intermolecular hydrogen bonds, resulting in the formation of three dimensional network (Fig. 3).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level.
	Fig. 2. The layered crystal packing of the title compound viewed down the b axis.
	Fig. 3. The crystal packing, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

trans-3-(2-Chloro-3-quinolyl)-1-phenyl-2,3-epoxypropan-1-one top

Crystal data top

C₁₈H₁₂ClNO₂	F(000) = 640
M_r = 309.74	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 1765 reflections
a = 11.0782 (19) Å	θ = 2.6–25.5°
b = 9.6177 (19) Å	µ = 0.28 mm⁻¹
c = 13.352 (3) Å	T = 295 K
β = 96.511 (9)°	Needle, white
V = 1413.4 (5) Å³	0.15 × 0.11 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	R_int = 0.055
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
CCD rotation images, thin slices, φ scans, and ω scans	h = −14→13
9724 measured reflections	k = −12→12
3164 independent reflections	l = −16→17
2291 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0448P)² + 0.3701P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3164 reflections	Δρ_max = 0.36 e Å⁻³
205 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₈H₁₂ClNO₂	V = 1413.4 (5) Å³
M_r = 309.74	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 11.0782 (19) Å	µ = 0.28 mm⁻¹
b = 9.6177 (19) Å	T = 295 K
c = 13.352 (3) Å	0.15 × 0.11 × 0.06 mm
β = 96.511 (9)°

Data collection top

Bruker APEXII diffractometer	2291 reflections with I > 2σ(I)
9724 measured reflections	R_int = 0.055
3164 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
3164 reflections	Δρ_min = −0.27 e Å⁻³
205 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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

	x	y	z	U_iso*/U_eq
Cl1	0.44660 (5)	0.15265 (5)	0.36554 (4)	0.0236 (2)
O1	0.04229 (14)	0.17899 (15)	0.13407 (12)	0.0278 (5)
O2	0.16982 (13)	0.41881 (14)	0.19793 (12)	0.0265 (5)
N1	0.56767 (15)	0.38265 (16)	0.39598 (13)	0.0185 (5)
C2	0.46357 (19)	0.33260 (18)	0.35826 (15)	0.0179 (6)
C3	0.36441 (18)	0.41018 (19)	0.30987 (15)	0.0176 (6)
C4	0.38174 (18)	0.55056 (19)	0.30233 (15)	0.0181 (6)
C5	0.49167 (18)	0.61229 (19)	0.34310 (15)	0.0170 (6)
C6	0.51367 (19)	0.7576 (2)	0.34001 (16)	0.0202 (6)
C7	0.6217 (2)	0.8103 (2)	0.38244 (16)	0.0224 (7)
C8	0.71302 (19)	0.7227 (2)	0.42894 (16)	0.0218 (7)
C9	0.69491 (18)	0.5820 (2)	0.43224 (16)	0.0200 (6)
C10	0.58343 (18)	0.52412 (19)	0.39002 (15)	0.0176 (6)
C11	0.24984 (18)	0.3409 (2)	0.26948 (16)	0.0200 (6)
C12	0.22971 (19)	0.3004 (2)	0.16239 (16)	0.0204 (7)
C13	0.15213 (19)	0.1740 (2)	0.13606 (16)	0.0204 (7)
C14	0.21784 (19)	0.0425 (2)	0.11805 (16)	0.0201 (6)
C15	0.34163 (19)	0.0396 (2)	0.10980 (16)	0.0243 (7)
C16	0.3989 (2)	−0.0854 (2)	0.09571 (18)	0.0284 (7)
C17	0.3340 (2)	−0.2086 (2)	0.09239 (16)	0.0266 (7)
C18	0.2115 (2)	−0.2074 (2)	0.10231 (18)	0.0315 (8)
C19	0.1532 (2)	−0.0821 (2)	0.11422 (18)	0.0280 (7)
H4	0.32027	0.60569	0.26996	0.0217*
H6	0.45435	0.81675	0.30903	0.0242*
H7	0.63515	0.90568	0.38061	0.0269*
H8	0.78615	0.76057	0.45762	0.0262*
H9	0.75609	0.52450	0.46231	0.0239*
H11	0.21102	0.28255	0.31677	0.0240*
H12	0.29615	0.31800	0.12147	0.0244*
H15	0.38607	0.12183	0.11377	0.0292*
H16	0.48134	−0.08671	0.08842	0.0340*
H17	0.37322	−0.29249	0.08344	0.0320*
H18	0.16824	−0.29038	0.10102	0.0378*
H19	0.07030	−0.08110	0.11969	0.0337*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0245 (3)	0.0128 (2)	0.0340 (3)	−0.0001 (2)	0.0056 (2)	0.0010 (2)
O1	0.0169 (9)	0.0316 (9)	0.0350 (10)	−0.0018 (6)	0.0039 (7)	−0.0073 (7)
O2	0.0214 (9)	0.0200 (7)	0.0366 (9)	0.0046 (6)	−0.0028 (7)	−0.0039 (6)
N1	0.0185 (9)	0.0161 (8)	0.0214 (9)	0.0000 (7)	0.0040 (7)	−0.0003 (6)
C2	0.0211 (12)	0.0125 (9)	0.0212 (11)	0.0009 (8)	0.0067 (9)	−0.0008 (7)
C3	0.0172 (11)	0.0165 (9)	0.0196 (10)	0.0001 (8)	0.0049 (8)	−0.0009 (8)
C4	0.0178 (11)	0.0174 (9)	0.0191 (10)	0.0025 (8)	0.0024 (9)	0.0005 (8)
C5	0.0164 (11)	0.0167 (9)	0.0184 (10)	0.0008 (8)	0.0045 (8)	−0.0003 (7)
C6	0.0211 (12)	0.0164 (9)	0.0234 (11)	0.0011 (8)	0.0041 (9)	0.0013 (8)
C7	0.0254 (13)	0.0148 (10)	0.0279 (12)	−0.0038 (8)	0.0070 (10)	−0.0005 (8)
C8	0.0175 (12)	0.0234 (11)	0.0246 (12)	−0.0038 (8)	0.0025 (9)	−0.0037 (8)
C9	0.0155 (11)	0.0217 (10)	0.0225 (11)	0.0008 (8)	0.0015 (9)	−0.0004 (8)
C10	0.0186 (11)	0.0166 (9)	0.0182 (10)	0.0004 (8)	0.0049 (8)	−0.0008 (8)
C11	0.0165 (11)	0.0168 (9)	0.0269 (12)	0.0009 (8)	0.0032 (9)	−0.0008 (8)
C12	0.0157 (12)	0.0192 (10)	0.0265 (12)	0.0001 (8)	0.0032 (9)	−0.0015 (8)
C13	0.0167 (12)	0.0237 (11)	0.0208 (11)	−0.0032 (8)	0.0017 (9)	−0.0013 (8)
C14	0.0175 (12)	0.0205 (10)	0.0223 (11)	−0.0021 (8)	0.0021 (9)	−0.0019 (8)
C15	0.0223 (13)	0.0213 (10)	0.0291 (12)	−0.0027 (8)	0.0019 (10)	0.0017 (9)
C16	0.0211 (12)	0.0295 (12)	0.0344 (13)	0.0041 (9)	0.0028 (10)	0.0028 (10)
C17	0.0344 (14)	0.0223 (10)	0.0229 (12)	0.0068 (9)	0.0020 (10)	−0.0010 (9)
C18	0.0370 (15)	0.0223 (11)	0.0349 (14)	−0.0085 (10)	0.0029 (11)	−0.0062 (9)
C19	0.0223 (12)	0.0291 (12)	0.0331 (13)	−0.0069 (9)	0.0048 (10)	−0.0069 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.7448 (18)	C14—C15	1.389 (3)
O1—C13	1.215 (3)	C14—C19	1.394 (3)
O2—C11	1.438 (3)	C15—C16	1.382 (3)
O2—C12	1.426 (2)	C16—C17	1.384 (3)
N1—C2	1.298 (3)	C17—C18	1.378 (3)
N1—C10	1.375 (2)	C18—C19	1.385 (3)
C2—C3	1.421 (3)	C4—H4	0.9300
C3—C4	1.369 (3)	C6—H6	0.9300
C3—C11	1.480 (3)	C7—H7	0.9300
C4—C5	1.408 (3)	C8—H8	0.9300
C5—C6	1.420 (3)	C9—H9	0.9300
C5—C10	1.414 (3)	C11—H11	0.9800
C6—C7	1.363 (3)	C12—H12	0.9800
C7—C8	1.406 (3)	C15—H15	0.9300
C8—C9	1.369 (3)	C16—H16	0.9300
C9—C10	1.412 (3)	C17—H17	0.9300
C11—C12	1.474 (3)	C18—H18	0.9300
C12—C13	1.507 (3)	C19—H19	0.9300
C13—C14	1.492 (3)

Cl1···C15	3.646 (2)	C15···H12	2.7300
Cl1···C7ⁱ	3.550 (2)	C16···H6^ix	3.0000
Cl1···C8ⁱ	3.633 (2)	C17···H6^ix	3.0500
Cl1···H11	2.9000	C17···H4^ix	2.9900
Cl1···H9ⁱⁱ	3.1100	C17···H12^viii	3.0600
Cl1···H11ⁱⁱⁱ	3.1300	C18···H4^ix	3.0100
O1···O2	2.787 (2)	C18···H12^viii	2.9900
O1···C2ⁱⁱ	3.213 (3)	H4···O2	2.5600
O1···C3ⁱⁱ	3.343 (3)	H4···C17^x	2.9900
O2···O1	2.787 (2)	H4···C18^x	3.0100
O1···H19	2.5300	H4···H6	2.5300
O1···H12ⁱⁱ	2.7100	H4···C7^v	2.9100
O1···H15ⁱⁱ	2.5800	H4···C8^v	3.0400
O2···H4	2.5600	H6···C16^x	3.0000
O2···H16ⁱⁱ	2.9000	H6···C17^x	3.0500
N1···H8^iv	2.6700	H6···H4	2.5300
N1···H11ⁱⁱⁱ	2.5600	H7···H9^xi	2.5700
C2···C9ⁱ	3.563 (3)	H7···C4^vi	3.0600
C2···O1ⁱⁱⁱ	3.213 (3)	H8···N1^xi	2.6700
C3···C9ⁱ	3.579 (3)	H8···C4^vi	3.0400
C3···O1ⁱⁱⁱ	3.343 (3)	H9···H7^iv	2.5700
C4···C7^v	3.454 (3)	H9···Cl1ⁱⁱⁱ	3.1100
C4···C8^v	3.439 (3)	H11···Cl1	2.9000
C7···Cl1ⁱ	3.550 (2)	H11···Cl1ⁱⁱ	3.1300
C7···C4^vi	3.454 (3)	H11···N1ⁱⁱ	2.5600
C8···Cl1ⁱ	3.633 (2)	H11···C2ⁱⁱ	3.0600
C8···C4^vi	3.439 (3)	H12···C15	2.7300
C9···C2ⁱ	3.563 (3)	H12···H15	2.1400
C9···C3ⁱ	3.579 (3)	H12···C17^vii	3.0600
C12···C17^vii	3.396 (3)	H12···C18^vii	2.9900
C13···C17^vii	3.273 (3)	H12···O1ⁱⁱⁱ	2.7100
C15···Cl1	3.646 (2)	H15···C12	2.5700
C17···C13^viii	3.273 (3)	H15···H12	2.1400
C17···C12^viii	3.396 (3)	H15···O1ⁱⁱⁱ	2.5800
C2···H11ⁱⁱⁱ	3.0600	H16···O2ⁱⁱⁱ	2.9000
C4···H7^v	3.0600	H16···H18^xii	2.3700
C4···H8^v	3.0400	H17···C13^viii	2.9300
C7···H4^vi	2.9100	H17···H19^xii	2.5000
C8···H4^vi	3.0400	H18···H16^xiii	2.3700
C12···H15	2.5700	H19···O1	2.5300
C13···H17^vii	2.9300	H19···H17^xiii	2.5000

C11—O2—C12	61.96 (13)	C14—C15—C16	120.07 (19)
C2—N1—C10	117.24 (17)	C15—C16—C17	120.3 (2)
Cl1—C2—N1	116.30 (15)	C16—C17—C18	120.22 (19)
Cl1—C2—C3	117.61 (15)	C17—C18—C19	119.69 (19)
N1—C2—C3	126.07 (17)	C14—C19—C18	120.5 (2)
C2—C3—C4	116.33 (18)	C3—C4—H4	120.00
C2—C3—C11	121.06 (16)	C5—C4—H4	120.00
C4—C3—C11	122.60 (18)	C5—C6—H6	120.00
C3—C4—C5	120.66 (18)	C7—C6—H6	120.00
C4—C5—C6	123.21 (18)	C6—C7—H7	119.00
C4—C5—C10	117.73 (17)	C8—C7—H7	120.00
C6—C5—C10	119.07 (18)	C7—C8—H8	120.00
C5—C6—C7	119.97 (19)	C9—C8—H8	120.00
C6—C7—C8	120.99 (18)	C8—C9—H9	120.00
C7—C8—C9	120.38 (19)	C10—C9—H9	120.00
C8—C9—C10	120.08 (18)	O2—C11—H11	116.00
N1—C10—C5	121.95 (18)	C3—C11—H11	116.00
N1—C10—C9	118.54 (17)	C12—C11—H11	116.00
C5—C10—C9	119.50 (17)	O2—C12—H12	117.00
O2—C11—C3	116.49 (16)	C11—C12—H12	117.00
O2—C11—C12	58.62 (13)	C13—C12—H12	117.00
C3—C11—C12	120.10 (18)	C14—C15—H15	120.00
O2—C12—C11	59.42 (13)	C16—C15—H15	120.00
O2—C12—C13	116.57 (17)	C15—C16—H16	120.00
C11—C12—C13	117.31 (18)	C17—C16—H16	120.00
O1—C13—C12	121.09 (18)	C16—C17—H17	120.00
O1—C13—C14	122.38 (18)	C18—C17—H17	120.00
C12—C13—C14	116.46 (18)	C17—C18—H18	120.00
C13—C14—C15	122.28 (18)	C19—C18—H18	120.00
C13—C14—C19	118.46 (19)	C14—C19—H19	120.00
C15—C14—C19	119.19 (18)	C18—C19—H19	120.00

C12—O2—C11—C3	110.6 (2)	C5—C6—C7—C8	0.5 (3)
C11—O2—C12—C13	107.5 (2)	C6—C7—C8—C9	0.1 (3)
C10—N1—C2—Cl1	179.30 (15)	C7—C8—C9—C10	−0.9 (3)
C10—N1—C2—C3	1.0 (3)	C8—C9—C10—N1	−179.05 (19)
C2—N1—C10—C5	−1.3 (3)	C8—C9—C10—C5	1.0 (3)
C2—N1—C10—C9	178.74 (19)	O2—C11—C12—C13	−106.2 (2)
Cl1—C2—C3—C4	−177.93 (15)	C3—C11—C12—O2	−104.50 (19)
Cl1—C2—C3—C11	1.5 (3)	C3—C11—C12—C13	149.27 (18)
N1—C2—C3—C4	0.4 (3)	O2—C12—C13—O1	8.4 (3)
N1—C2—C3—C11	179.8 (2)	O2—C12—C13—C14	−168.62 (18)
C2—C3—C4—C5	−1.5 (3)	C11—C12—C13—O1	75.9 (3)
C11—C3—C4—C5	179.12 (19)	C11—C12—C13—C14	−101.1 (2)
C2—C3—C11—O2	−162.68 (18)	O1—C13—C14—C15	173.1 (2)
C2—C3—C11—C12	−95.2 (2)	O1—C13—C14—C19	−10.0 (3)
C4—C3—C11—O2	16.7 (3)	C12—C13—C14—C15	−10.0 (3)
C4—C3—C11—C12	84.2 (3)	C12—C13—C14—C19	166.9 (2)
C3—C4—C5—C6	−178.3 (2)	C13—C14—C15—C16	178.3 (2)
C3—C4—C5—C10	1.2 (3)	C19—C14—C15—C16	1.4 (3)
C4—C5—C6—C7	179.0 (2)	C13—C14—C19—C18	−177.0 (2)
C10—C5—C6—C7	−0.4 (3)	C15—C14—C19—C18	0.0 (3)
C4—C5—C10—N1	0.3 (3)	C14—C15—C16—C17	−1.7 (3)
C4—C5—C10—C9	−179.75 (19)	C15—C16—C17—C18	0.5 (3)
C6—C5—C10—N1	179.68 (19)	C16—C17—C18—C19	0.9 (3)
C6—C5—C10—C9	−0.3 (3)	C17—C18—C19—C14	−1.2 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+1/2, z; (iii) x+1/2, −y+1/2, z; (iv) −x+3/2, y−1/2, −z+1; (v) x−1/2, −y+3/2, z; (vi) x+1/2, −y+3/2, z; (vii) −x+1/2, y+1/2, −z; (viii) −x+1/2, y−1/2, −z; (ix) x, y−1, z; (x) x, y+1, z; (xi) −x+3/2, y+1/2, −z+1; (xii) x+1/2, −y−1/2, z; (xiii) x−1/2, −y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.9300	2.5600	2.884 (3)	101.00
C11—H11···N1ⁱⁱ	0.9800	2.5600	3.510 (3)	164.00
C15—H15···O1ⁱⁱⁱ	0.9300	2.5800	3.494 (3)	170.00

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂ClNO₂
M_r	309.74
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	295
a, b, c (Å)	11.0782 (19), 9.6177 (19), 13.352 (3)
β (°)	96.511 (9)
V (Å³)	1413.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.15 × 0.11 × 0.06

Data collection
Diffractometer	Bruker APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9724, 3164, 2291
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.109, 1.02
No. of reflections	3164
No. of parameters	205
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.27

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).