(2E)-3-(2-Chloro-6-methyl-3-quinol­yl)-1-(1-naphth­yl)prop-2-en-1-one

Rizvi, S.U.F.; Siddiqui, H.L.; Zia-ur-Rehman, M.; Azam, M.; Parvez, M.

doi:10.1107/S1600536810007828

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o761

doi:10.1107/S1600536810007828

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(2E)-3-(2-Chloro-6-methyl-3-quinolyl)-1-(1-naphthyl)prop-2-en-1-one

Syed Umar Farooq Rizvi,^a Hamid Latif Siddiqui,^a ^* Muhammad Zia-ur-Rehman,^b Muhammad Azam ^c and Masood Parvez ^d

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, ^cInstitute of Biochemistry, University of Balochistan, Quetta 8700, Pakistan, and ^dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 22 February 2010; accepted 1 March 2010; online 6 March 2010)

In the title molecule, C₂₃H₁₆ClNO, the quinoline and naphthalene ring systems are individually planar, with maximum deviations of 0.020 (2) and 0.033 (2) Å, respectively, and are inclined at a dihedral angle of 30.01 (4)°. Intramolecular C—H⋯O and C—H⋯Cl interactions occur. The crystal structure is devoid of any classical hydrogen bonds, but symmetry-related molecules are linked via weak C—H⋯Cl interactions, forming chains propagating in [001].

Related literature

For background literature on chalcones, see: Drexler & Amiridis (2003 ); Opletalova & Sedivy (1999 ); Oyedapo et al. (2004 ); Prabhavat & Ghiya (1998 ); Varga et al. (2003 ). For bond distances, see: Allen (2002 ). For the preparation of 2-chloro-6-methyl-3-formylquinoline, see: Meth-Cohn et al. (1981 ).

Experimental

Crystal data

C₂₃H₁₆ClNO
M_r = 357.82
Monoclinic, P 2₁ /c
a = 16.919 (8) Å
b = 7.146 (3) Å
c = 14.829 (5) Å
β = 103.29 (2)°
V = 1744.9 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.14 × 0.12 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.968, T_max = 0.989
6886 measured reflections
3988 independent reflections
2575 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.131
S = 1.01
3988 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cl1ⁱ	0.95	2.86	3.792 (2)	166
C11—H11⋯Cl1	0.95	2.65	3.045 (2)	106
C11—H11⋯O1	0.95	2.45	2.788 (3)	101
C22—H22⋯O1	0.95	2.33	2.924 (3)	120
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007828/su2165sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007828/su2165Isup2.hkl

checkCIF report

Comment top

1,3-Diaryl-2-propen-1-ones, commonly known as chalcones, are normally synthesized by Claisen-Schmidt condensation (Oyedapo et al., 2004). They are used as precursors to synthesize many heterocyclic compounds like flavonoids (Drexler & Amiridis, 2003), pyrimidines, imidazoles (Varga et al., 2003) etc. Chalcones have already been recognized as anti-bacterial, anti-tuberculous, anti-tumor, anti-inflammatory, anti-viral, anti-microbial and anti-protozoal gastroprotective agents (Opletalova & Sedivy, 1999). They may also be converted to 2-mercaptopyrimidines, which have anti-cancer, anti-tubercular and anti-AIDS activities, by the reaction with thiourea (Prabhavat & Ghiya, 1998). A series of similar chalcones is under investigation in our laboratory for their biological activities. We report here on the synthesis and crystal structure of a new chalcone, containing a quinolyl ring system, (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(naphthalen-1-yl)prop-2-en-1-one.

The title molecule is presented in Fig. 1. The bond distances are as expected (Allen, 2002). The mean planes of the quinoline and naphthalene rings, defined by atoms N1/C1—C9 and C14—C23, respectively, are individually planar with maximum deviations of 0.020 (2) and 0.033 (2) Å, respectively. These planes are inclined at 30.01 (4)° with respect to each other.

The crystal structure is devoid of any classical hydrogen bonds, however in the molecule itself short intramolecular interactions involving atoms Cl1 and O1 are present (Table 1). In the crystal structure a weak C-H···Cl interaction links the molecules to form chains propagating in [001]; see Table 1 and Fig. 2 for details.

Related literature top

For background literature on chalcones, see: Drexler & Amiridis (2003); Opletalova & Sedivy (1999); Oyedapo et al. (2004); Prabhavat & Ghiya (1998); Varga et al. (2003). For bond distances, see: Allen (2002). For the preparation of 2-chloro-6-methyl-3-formylquinoline, see: Meth-Cohn et al. (1981).

Experimental top

2-Chloro-6-methyl-3-formylquinoline was prepared by the literature procedure (Meth-Cohn et al., 1981). A mixture of 2-chloro-6-methyl-3-formylquinoline (2.055 g, 10.0 mmol), 1-acetylnaphthalene (1.7021 g, 10.0 mmol) and methanol (50 ml) was stirred at RT, and an aqueous solution of sodium hydroxide (4.0 ml, 10 %) was added dropwise. The mixture was stirred overnight and was then pored into ice-cold water (200 ml). The precipitates obtained were collected by filtration, washed first with cold water and then with cold methanol. Recrystallization from chloroform gave pale-yellow crystals (yield: 2.90 g; 8.11 mmol, 81.0%), (m.p. 433-435 K).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title molecule, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view along the b-axis of the crystal packing of the title compound, showing the C—H···Cl interactions as dashed lines [see Table 1 for details; H-atoms not involved in hydrogen bonds have been omitted for clarity].

(2E)-3-(2-Chloro-6-methyl-3-quinolyl)-1-(1-naphthyl)prop-2-en-1-one top

Crystal data top

C₂₃H₁₆ClNO	F(000) = 744
M_r = 357.82	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6886 reflections
a = 16.919 (8) Å	θ = 2.8–27.5°
b = 7.146 (3) Å	µ = 0.23 mm⁻¹
c = 14.829 (5) Å	T = 173 K
β = 103.29 (2)°	Plate, light yellow
V = 1744.9 (13) Å³	0.14 × 0.12 × 0.05 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3988 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −21→21
T_min = 0.968, T_max = 0.989	k = −8→9
6886 measured reflections	l = −19→19

Refinement top

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F²) = 0.131	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0545P)² + 0.6476P] where P = (F_o² + 2F_c²)/3
3988 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₃H₁₆ClNO	V = 1744.9 (13) Å³
M_r = 357.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.919 (8) Å	µ = 0.23 mm⁻¹
b = 7.146 (3) Å	T = 173 K
c = 14.829 (5) Å	0.14 × 0.12 × 0.05 mm
β = 103.29 (2)°

Data collection top

Nonius KappaCCD diffractometer	3988 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2575 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.989	R_int = 0.039
6886 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
3988 reflections	Δρ_min = −0.29 e Å⁻³
236 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 > 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	0.05985 (4)	0.69090 (9)	0.33367 (3)	0.0466 (2)
O1	0.29189 (9)	0.9031 (2)	0.21743 (9)	0.0428 (4)
N1	−0.07435 (11)	0.6646 (3)	0.20914 (11)	0.0364 (4)
C1	−0.12197 (12)	0.6652 (3)	0.11997 (13)	0.0319 (5)
C2	−0.20482 (13)	0.6170 (3)	0.10550 (15)	0.0378 (5)
H2	−0.2275	0.5874	0.1567	0.045*
C3	−0.25230 (13)	0.6132 (3)	0.01723 (15)	0.0374 (5)
H3	−0.3080	0.5801	0.0081	0.045*
C4	−0.22076 (13)	0.6572 (3)	−0.06116 (14)	0.0353 (5)
C5	−0.14061 (13)	0.7047 (3)	−0.04742 (14)	0.0344 (5)
H5	−0.1190	0.7363	−0.0992	0.041*
C6	−0.08912 (13)	0.7078 (3)	0.04277 (13)	0.0314 (5)
C7	−0.00604 (13)	0.7522 (3)	0.05985 (14)	0.0338 (5)
H7	0.0172	0.7835	0.0092	0.041*
C8	0.04260 (13)	0.7514 (3)	0.14841 (13)	0.0317 (5)
C9	0.00187 (13)	0.7035 (3)	0.21931 (13)	0.0328 (5)
C10	−0.27558 (15)	0.6499 (4)	−0.15703 (16)	0.0481 (6)
H10A	−0.2452	0.6896	−0.2026	0.058*
H10B	−0.3219	0.7338	−0.1600	0.058*
H10C	−0.2952	0.5217	−0.1708	0.058*
C11	0.12863 (13)	0.8006 (3)	0.16855 (13)	0.0340 (5)
H11	0.1533	0.8344	0.2306	0.041*
C12	0.17573 (13)	0.8023 (3)	0.10796 (14)	0.0338 (5)
H12	0.1535	0.7696	0.0452	0.041*
C13	0.26277 (13)	0.8548 (3)	0.13762 (13)	0.0322 (5)
C14	0.31294 (12)	0.8425 (3)	0.06743 (13)	0.0295 (5)
C15	0.27849 (14)	0.8918 (3)	−0.02286 (13)	0.0361 (5)
H15	0.2231	0.9285	−0.0390	0.043*
C16	0.32305 (16)	0.8890 (4)	−0.09110 (15)	0.0551 (7)
H16	0.2983	0.9253	−0.1528	0.066*
C17	0.40178 (17)	0.8344 (5)	−0.06904 (16)	0.0718 (10)
H17	0.4316	0.8325	−0.1160	0.086*
C18	0.44086 (14)	0.7800 (4)	0.02193 (15)	0.0489 (7)
C19	0.52216 (17)	0.7176 (5)	0.04411 (19)	0.0776 (11)
H19	0.5520	0.7158	−0.0029	0.093*
C20	0.55878 (16)	0.6603 (5)	0.13079 (18)	0.0637 (8)
H20	0.6136	0.6191	0.1443	0.076*
C21	0.51529 (14)	0.6622 (3)	0.19988 (16)	0.0439 (6)
H21	0.5407	0.6211	0.2605	0.053*
C22	0.43669 (13)	0.7222 (3)	0.18163 (14)	0.0361 (5)
H22	0.4084	0.7225	0.2300	0.043*
C23	0.39635 (12)	0.7843 (3)	0.09213 (13)	0.0309 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0431 (4)	0.0673 (4)	0.0265 (3)	−0.0126 (3)	0.0024 (2)	0.0045 (3)
O1	0.0350 (9)	0.0637 (11)	0.0287 (7)	−0.0057 (8)	0.0053 (6)	−0.0084 (7)
N1	0.0347 (11)	0.0459 (11)	0.0292 (9)	−0.0018 (9)	0.0088 (7)	0.0014 (8)
C1	0.0296 (12)	0.0357 (12)	0.0304 (10)	0.0007 (9)	0.0069 (8)	−0.0012 (9)
C2	0.0325 (12)	0.0425 (14)	0.0404 (11)	0.0001 (10)	0.0122 (9)	0.0013 (10)
C3	0.0278 (12)	0.0360 (13)	0.0471 (12)	0.0011 (10)	0.0056 (9)	−0.0001 (10)
C4	0.0336 (12)	0.0302 (12)	0.0387 (11)	0.0032 (9)	0.0014 (9)	−0.0003 (9)
C5	0.0365 (13)	0.0357 (12)	0.0306 (10)	−0.0006 (10)	0.0071 (9)	0.0002 (9)
C6	0.0310 (12)	0.0334 (12)	0.0301 (10)	0.0008 (9)	0.0074 (8)	−0.0015 (9)
C7	0.0340 (12)	0.0409 (13)	0.0282 (10)	−0.0013 (10)	0.0107 (8)	−0.0011 (9)
C8	0.0301 (11)	0.0371 (12)	0.0284 (10)	−0.0013 (9)	0.0081 (8)	−0.0031 (9)
C9	0.0329 (12)	0.0396 (13)	0.0256 (9)	−0.0005 (10)	0.0059 (8)	−0.0007 (9)
C10	0.0419 (14)	0.0500 (15)	0.0448 (13)	−0.0038 (12)	−0.0056 (11)	0.0043 (11)
C11	0.0318 (12)	0.0404 (13)	0.0287 (10)	−0.0021 (10)	0.0043 (8)	−0.0006 (9)
C12	0.0298 (11)	0.0418 (13)	0.0284 (9)	−0.0005 (10)	0.0041 (8)	−0.0034 (9)
C13	0.0297 (12)	0.0363 (12)	0.0294 (10)	−0.0014 (9)	0.0041 (8)	−0.0007 (9)
C14	0.0277 (11)	0.0319 (12)	0.0277 (9)	−0.0013 (9)	0.0039 (8)	−0.0022 (8)
C15	0.0323 (12)	0.0427 (13)	0.0309 (10)	0.0031 (10)	0.0023 (9)	0.0004 (9)
C16	0.0447 (15)	0.093 (2)	0.0267 (11)	0.0093 (14)	0.0061 (10)	0.0086 (12)
C17	0.0466 (17)	0.142 (3)	0.0321 (12)	0.0179 (18)	0.0187 (11)	0.0051 (16)
C18	0.0329 (13)	0.080 (2)	0.0340 (11)	0.0100 (13)	0.0085 (9)	−0.0020 (12)
C19	0.0408 (16)	0.148 (3)	0.0466 (14)	0.0298 (19)	0.0155 (12)	−0.0024 (18)
C20	0.0354 (15)	0.094 (2)	0.0567 (16)	0.0209 (15)	0.0012 (12)	−0.0071 (15)
C21	0.0383 (14)	0.0456 (14)	0.0409 (12)	0.0005 (11)	−0.0051 (10)	0.0013 (11)
C22	0.0321 (12)	0.0404 (13)	0.0335 (11)	−0.0040 (10)	0.0025 (9)	0.0028 (9)
C23	0.0281 (11)	0.0341 (12)	0.0290 (10)	−0.0021 (9)	0.0035 (8)	−0.0033 (9)

Geometric parameters (Å, º) top

Cl1—C9	1.755 (2)	C11—H11	0.9500
O1—C13	1.222 (2)	C12—C13	1.485 (3)
N1—C9	1.294 (3)	C12—H12	0.9500
N1—C1	1.381 (3)	C13—C14	1.489 (3)
C1—C2	1.411 (3)	C14—C15	1.378 (3)
C1—C6	1.416 (3)	C14—C23	1.436 (3)
C2—C3	1.370 (3)	C15—C16	1.394 (3)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.421 (3)	C16—C17	1.354 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.367 (3)	C17—C18	1.414 (3)
C4—C10	1.509 (3)	C17—H17	0.9500
C5—C6	1.419 (3)	C18—C19	1.411 (4)
C5—H5	0.9500	C18—C23	1.418 (3)
C6—C7	1.406 (3)	C19—C20	1.356 (4)
C7—C8	1.380 (3)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.392 (4)
C8—C9	1.425 (3)	C20—H20	0.9500
C8—C11	1.460 (3)	C21—C22	1.364 (3)
C10—H10A	0.9800	C21—H21	0.9500
C10—H10B	0.9800	C22—C23	1.417 (3)
C10—H10C	0.9800	C22—H22	0.9500
C11—C12	1.331 (3)

C9—N1—C1	117.22 (17)	C11—C12—C13	120.61 (18)
N1—C1—C2	119.03 (18)	C11—C12—H12	119.7
N1—C1—C6	121.58 (19)	C13—C12—H12	119.7
C2—C1—C6	119.37 (18)	O1—C13—C12	120.64 (19)
C3—C2—C1	119.6 (2)	O1—C13—C14	121.71 (19)
C3—C2—H2	120.2	C12—C13—C14	117.64 (17)
C1—C2—H2	120.2	C15—C14—C23	119.57 (18)
C2—C3—C4	122.0 (2)	C15—C14—C13	118.85 (19)
C2—C3—H3	119.0	C23—C14—C13	121.57 (17)
C4—C3—H3	119.0	C14—C15—C16	121.6 (2)
C5—C4—C3	118.63 (19)	C14—C15—H15	119.2
C5—C4—C10	121.5 (2)	C16—C15—H15	119.2
C3—C4—C10	119.9 (2)	C17—C16—C15	119.7 (2)
C4—C5—C6	121.2 (2)	C17—C16—H16	120.2
C4—C5—H5	119.4	C15—C16—H16	120.2
C6—C5—H5	119.4	C16—C17—C18	121.9 (2)
C7—C6—C1	117.71 (18)	C16—C17—H17	119.1
C7—C6—C5	123.03 (19)	C18—C17—H17	119.1
C1—C6—C5	119.26 (19)	C19—C18—C17	121.8 (2)
C8—C7—C6	121.54 (19)	C19—C18—C23	119.3 (2)
C8—C7—H7	119.2	C17—C18—C23	118.9 (2)
C6—C7—H7	119.2	C20—C19—C18	121.7 (2)
C7—C8—C9	114.79 (19)	C20—C19—H19	119.2
C7—C8—C11	122.81 (19)	C18—C19—H19	119.2
C9—C8—C11	122.37 (18)	C19—C20—C21	119.4 (2)
N1—C9—C8	127.14 (18)	C19—C20—H20	120.3
N1—C9—Cl1	114.98 (15)	C21—C20—H20	120.3
C8—C9—Cl1	117.87 (16)	C22—C21—C20	120.9 (2)
C4—C10—H10A	109.5	C22—C21—H21	119.6
C4—C10—H10B	109.5	C20—C21—H21	119.6
H10A—C10—H10B	109.5	C21—C22—C23	121.5 (2)
C4—C10—H10C	109.5	C21—C22—H22	119.3
H10A—C10—H10C	109.5	C23—C22—H22	119.3
H10B—C10—H10C	109.5	C22—C23—C18	117.3 (2)
C12—C11—C8	125.99 (19)	C22—C23—C14	124.28 (19)
C12—C11—H11	117.0	C18—C23—C14	118.41 (18)
C8—C11—H11	117.0

C9—N1—C1—C2	177.8 (2)	C11—C12—C13—O1	−2.4 (3)
C9—N1—C1—C6	−0.4 (3)	C11—C12—C13—C14	176.4 (2)
N1—C1—C2—C3	−178.6 (2)	O1—C13—C14—C15	−143.8 (2)
C6—C1—C2—C3	−0.3 (3)	C12—C13—C14—C15	37.4 (3)
C1—C2—C3—C4	−0.3 (3)	O1—C13—C14—C23	34.9 (3)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C23	−143.8 (2)
C2—C3—C4—C10	179.7 (2)	C23—C14—C15—C16	−0.9 (3)
C3—C4—C5—C6	0.9 (3)	C13—C14—C15—C16	177.9 (2)
C10—C4—C5—C6	−178.8 (2)	C14—C15—C16—C17	0.9 (4)
N1—C1—C6—C7	−0.8 (3)	C15—C16—C17—C18	−0.2 (5)
C2—C1—C6—C7	−179.0 (2)	C16—C17—C18—C19	178.0 (3)
N1—C1—C6—C5	179.4 (2)	C16—C17—C18—C23	−0.5 (5)
C2—C1—C6—C5	1.2 (3)	C17—C18—C19—C20	−178.0 (3)
C4—C5—C6—C7	178.7 (2)	C23—C18—C19—C20	0.5 (5)
C4—C5—C6—C1	−1.5 (3)	C18—C19—C20—C21	0.2 (5)
C1—C6—C7—C8	1.1 (3)	C19—C20—C21—C22	−0.5 (5)
C5—C6—C7—C8	−179.1 (2)	C20—C21—C22—C23	0.1 (4)
C6—C7—C8—C9	−0.3 (3)	C21—C22—C23—C18	0.5 (3)
C6—C7—C8—C11	−178.7 (2)	C21—C22—C23—C14	177.5 (2)
C1—N1—C9—C8	1.5 (3)	C19—C18—C23—C22	−0.8 (4)
C1—N1—C9—Cl1	−177.48 (16)	C17—C18—C23—C22	177.7 (3)
C7—C8—C9—N1	−1.1 (3)	C19—C18—C23—C14	−178.0 (3)
C11—C8—C9—N1	177.3 (2)	C17—C18—C23—C14	0.5 (4)
C7—C8—C9—Cl1	177.80 (17)	C15—C14—C23—C22	−176.9 (2)
C11—C8—C9—Cl1	−3.7 (3)	C13—C14—C23—C22	4.4 (3)
C7—C8—C11—C12	−19.2 (4)	C15—C14—C23—C18	0.1 (3)
C9—C8—C11—C12	162.5 (2)	C13—C14—C23—C18	−178.6 (2)
C8—C11—C12—C13	−179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1ⁱ	0.95	2.86	3.792 (2)	166
C11—H11···Cl1	0.95	2.65	3.045 (2)	106
C11—H11···O1	0.95	2.45	2.788 (3)	101
C22—H22···O1	0.95	2.33	2.924 (3)	120

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₆ClNO
M_r	357.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.919 (8), 7.146 (3), 14.829 (5)
β (°)	103.29 (2)
V (Å³)	1744.9 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.14 × 0.12 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.968, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6886, 3988, 2575
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.131, 1.01
No. of reflections	3988
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.29

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1ⁱ	0.95	2.86	3.792 (2)	166
C11—H11···Cl1	0.95	2.65	3.045 (2)	106
C11—H11···O1	0.95	2.45	2.788 (3)	101
C22—H22···O1	0.95	2.33	2.924 (3)	120

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for a grant to carry out this work.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Drexler, M. T. & Amiridis, M. D. (2003). J. Catal. 214, 136–145. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Meth-Cohn, O., Narine, B. & Tarnowski, B. (1981). J. Chem. Soc. Perkin Trans. 1, pp. 1520–530. CrossRef Web of Science Google Scholar
Opletalova, V. & Sedivy, D. (1999). Ceska Slov. Farm. 48, 252–255. PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Oyedapo, A. O., Makanju, V. O., Adewunmi, C. O., Iwalewa, E. O. & Adenowo, T. K. (2004). Afr. J. Trad. CAM. 1, 55–62. CAS Google Scholar
Prabhavat, M. & Ghiya, B. (1998). Indian J. Heterocycl. Chem. 7, 311–312. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Varga, L., Nagy, T., Kövesdi, I., Jordi, B.-B., Dormán, G., Ürge, L. & Darvas, F. (2003). Tetrahedron, 59, 655–662. Web of Science CSD CrossRef CAS Google Scholar