1-[(2-Chloro-7,8-dimethyl­quinolin-3-yl)meth­yl]pyridin-2(1H)-one

Khan, F.N.; Roopan, S.M.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810011505

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o1001

doi:10.1107/S1600536810011505

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1-[(2-Chloro-7,8-dimethylquinolin-3-yl)methyl]pyridin-2(1H)-one

F. Nawaz Khan,^a S. Mohana Roopan,^a Venkatesha R. Hathwar ^b and Mehmet Akkurt ^c ^*

^aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 24 March 2010; accepted 26 March 2010; online 31 March 2010)

In the title compound, C₁₇H₁₅ClN₂O, the quinoline ring system is nearly planar, with a maximum deviation from the mean plane of 0.074 (2) Å, and makes a dihedral angle of 81.03 (7)° with the pyridone ring. The crystal packing is stabilized by π–π stacking interactions between the pyridone and benzene rings of the quinoline ring system [centroid–centroid distance = 3.6754 (10) Å]. Furthermore, weak intermolecular C—H⋯O hydrogen bonding links molecules into supramolecular chains along [001].

Related literature

For 2-pyridone analogues, see: Arman et al. (2009 ); Clegg & Nichol (2004 ); Nichol & Clegg (2005 ). For alkaloid analogues of natural or synthetic anticancer agents, see: Roopan & Khan (2009 ). For N-alkylation in organic synthesis, see: Roopan et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₅ClN₂O
M_r = 298.76
Monoclinic, P 2₁ /c
a = 7.07034 (17) Å
b = 15.4729 (4) Å
c = 13.1704 (3) Å
β = 96.342 (2)°
V = 1432.01 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.24 × 0.15 × 0.12 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.953, T_max = 0.968
15150 measured reflections
2810 independent reflections
2008 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.108
S = 1.06
2810 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.52	3.318 (2)	143
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011505/xu2741sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011505/xu2741Isup2.hkl

checkCIF report

Comment top

Compounds found in nature display a wide range of diversity in terms of their structures and physical and biological properties. Several alkaloid analogues of natural or synthetic anticancer agents (Roopan & Khan, 2009) are well known, and have attracted considerable interest because of their significant activity. Particularly, five and six membered heterocyclic compounds containing one or two hetero atoms fused to a quinoline ring are found in natural products. The search for new anticancer drugs from nature continues to be a fruitful activity, as evidenced by the successes of natural products as pharmaceutical agents. Nitrogen containing heterocyclic compounds, recognized pharmacophores has received great attention in drug discovery and lead optimization. The chemistry of N-alkylation has recently received much attention due to their usefulness as building blocks in organic synthesis (Roopan et al., 2010). On the basis of the interesting structures and biological activities exhibited by several heterocyclic systems possessing quinoline and pyridone nucleus, we have synthesized a quinoline coupled pyridone, i.e., 1-[(2-chloroquinolin-3yl)-methyl]-pyridine-2(1H)-one.

In the title molecule, Fig.1., the quinoline unit is nearly planar, with maximum deviations from the mean plane of -0.074 (2) Å for C2, -0.061 (2) Å for C6 and 0.059 (1) Å for N1 and 0.049 (2) Å for C4. The dihedral angle between the pyridine ring and the quinoline fused-ring system is 81.03 (7)°. Molecular conformation is stabilized by the intra molecular C—H···N and C—H···Cl interactions, forming a 5-membered ring. The crystal structure shows the presence of intermolecular π-π interactions between the pyridone (N2/C11–C15) and benzene (C4–C9) rings of the quinoline ring system, with the Cg2···Cg3(x, 1/2-y, 1/2+z) distance of 3.6754 (10) Å [Cg2 and Cg3 are the centroids of the N2/C11–C15 pyridone and C4–C9 benzene rings, respectively]. The molecular packing is further stabilized by weak intermolecular C—H···O interactions (Table1, Fig. 2), forming chains in the [001] direction.

Related literature top

For 2-pyridone analogues, see: Arman et al. (2009); Clegg & Nichol (2004); Nichol & Clegg (2005). For alkaloid analogues of natural or synthetic anticancer agents, see: Roopan & Khan (2009). For N-alkylation in organic synthesis, see: Roopan et al. (2010).

Experimental top

To a mixed well solution of 2-pyridone (95 mg, 1 mmol, in 2 ml of DMF), KO^tBu (112 mg, 1 mmol in 10 ml of THF) and 2-chloro-3-(chloromethyl)-7,8-dimethylquinoline (240 mg, 1 mmol) were added and the resulting mixture was refluxed at 343 K for 1 h. After the completion of the reaction, cooled and removed the excess of solvent under reduced pressure. Crushed ice was mixed with the residue. White solid was formed, filtered and dried, purified by column chromatography using hexane and ethylacetate as the eluant. Crystals of suitable quality were grown by solvent evaporation from a solution of the compound in chloroform.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The packing and hydrogen bonding interactions of (I) viewing down the a-axis. H atoms not participating in hydrogen bonding have been omitted for clarity.

1-[(2-Chloro-7,8-dimethylquinolin-3-yl)methyl]pyridin-2(1H)-one top

Crystal data top

C₁₇H₁₅ClN₂O	F(000) = 624
M_r = 298.76	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1523 reflections
a = 7.07034 (17) Å	θ = 2.6–26.0°
b = 15.4729 (4) Å	µ = 0.27 mm⁻¹
c = 13.1704 (3) Å	T = 295 K
β = 96.342 (2)°	Block, colourless
V = 1432.01 (6) Å³	0.24 × 0.15 × 0.12 mm
Z = 4

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2810 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −8→8
T_min = 0.953, T_max = 0.968	k = −19→19
15150 measured reflections	l = −16→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
2810 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₅ClN₂O	V = 1432.01 (6) Å³
M_r = 298.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.07034 (17) Å	µ = 0.27 mm⁻¹
b = 15.4729 (4) Å	T = 295 K
c = 13.1704 (3) Å	0.24 × 0.15 × 0.12 mm
β = 96.342 (2)°

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2810 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	2008 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.968	R_int = 0.035
15150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	Δρ_max = 0.20 e Å⁻³
2810 reflections	Δρ_min = −0.20 e Å⁻³
192 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 esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	1.38101 (6)	0.30106 (3)	0.46949 (4)	0.0555 (2)
O1	0.8143 (2)	0.15968 (9)	0.50257 (10)	0.0645 (5)
N1	1.14556 (19)	0.39838 (9)	0.35696 (10)	0.0395 (5)
N2	0.8843 (2)	0.24988 (9)	0.63744 (10)	0.0401 (5)
C1	1.1608 (2)	0.35195 (10)	0.43917 (13)	0.0376 (5)
C2	1.0220 (2)	0.33920 (11)	0.50689 (12)	0.0379 (5)
C3	0.8596 (2)	0.38656 (11)	0.48572 (12)	0.0388 (6)
C4	0.6662 (2)	0.48857 (11)	0.37163 (14)	0.0448 (6)
C5	0.6463 (3)	0.53389 (12)	0.28258 (14)	0.0504 (7)
C6	0.7855 (3)	0.53271 (11)	0.21389 (14)	0.0465 (6)
C7	0.9535 (2)	0.48792 (11)	0.23822 (13)	0.0406 (6)
C8	0.9779 (2)	0.44201 (10)	0.33237 (12)	0.0347 (5)
C9	0.8327 (2)	0.44006 (10)	0.39814 (12)	0.0360 (5)
C10	1.0577 (3)	0.27637 (13)	0.59472 (14)	0.0485 (6)
C11	0.8430 (3)	0.28316 (12)	0.72898 (14)	0.0490 (7)
C12	0.6894 (3)	0.25858 (13)	0.77200 (14)	0.0533 (7)
C13	0.5686 (3)	0.19603 (12)	0.72202 (15)	0.0525 (7)
C14	0.6077 (3)	0.16224 (12)	0.63285 (14)	0.0490 (6)
C15	0.7703 (3)	0.18774 (11)	0.58469 (13)	0.0435 (6)
C16	0.7440 (3)	0.57702 (15)	0.11113 (15)	0.0744 (9)
C17	1.1065 (3)	0.48403 (13)	0.16669 (14)	0.0544 (7)
H3	0.76520	0.38360	0.52950	0.0470*
H4	0.57050	0.48960	0.41470	0.0540*
H5	0.53700	0.56680	0.26650	0.0600*
H10A	1.12000	0.22540	0.57130	0.0580*
H10B	1.14370	0.30290	0.64830	0.0580*
H11	0.92440	0.32400	0.76200	0.0590*
H12	0.66280	0.28230	0.83370	0.0640*
H13	0.46110	0.17800	0.75090	0.0630*
H14	0.52600	0.12080	0.60130	0.0590*
H16A	0.84350	0.61760	0.10210	0.1120*
H16B	0.62460	0.60700	0.10850	0.1120*
H16C	0.73740	0.53460	0.05770	0.1120*
H17A	1.06670	0.44600	0.11080	0.0820*
H17B	1.22240	0.46280	0.20300	0.0820*
H17C	1.12740	0.54080	0.14090	0.0820*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0391 (3)	0.0611 (4)	0.0671 (4)	0.0103 (2)	0.0101 (2)	0.0147 (2)
O1	0.0904 (11)	0.0639 (9)	0.0404 (7)	−0.0009 (8)	0.0126 (7)	−0.0064 (6)
N1	0.0385 (8)	0.0395 (8)	0.0416 (8)	−0.0019 (7)	0.0091 (6)	0.0031 (7)
N2	0.0456 (9)	0.0409 (8)	0.0341 (8)	−0.0025 (7)	0.0055 (7)	0.0053 (7)
C1	0.0338 (9)	0.0344 (9)	0.0446 (10)	0.0002 (7)	0.0046 (7)	0.0005 (8)
C2	0.0381 (9)	0.0360 (9)	0.0396 (9)	−0.0050 (8)	0.0047 (7)	0.0015 (7)
C3	0.0368 (10)	0.0403 (10)	0.0403 (9)	−0.0030 (8)	0.0090 (7)	−0.0005 (8)
C4	0.0429 (10)	0.0416 (10)	0.0512 (11)	0.0045 (8)	0.0106 (8)	−0.0010 (9)
C5	0.0489 (11)	0.0394 (11)	0.0617 (12)	0.0082 (9)	0.0012 (9)	0.0035 (9)
C6	0.0527 (11)	0.0379 (10)	0.0475 (11)	−0.0025 (9)	−0.0001 (9)	0.0069 (8)
C7	0.0452 (10)	0.0355 (10)	0.0409 (10)	−0.0057 (8)	0.0045 (8)	0.0004 (8)
C8	0.0357 (9)	0.0305 (9)	0.0383 (9)	−0.0026 (7)	0.0053 (7)	0.0007 (7)
C9	0.0357 (9)	0.0310 (9)	0.0413 (9)	−0.0027 (7)	0.0043 (7)	−0.0024 (7)
C10	0.0410 (10)	0.0559 (12)	0.0483 (11)	−0.0010 (9)	0.0041 (8)	0.0133 (9)
C11	0.0636 (13)	0.0443 (11)	0.0388 (10)	−0.0033 (10)	0.0042 (9)	−0.0013 (8)
C12	0.0699 (14)	0.0542 (12)	0.0382 (10)	0.0064 (10)	0.0166 (10)	0.0012 (9)
C13	0.0506 (12)	0.0581 (13)	0.0502 (12)	0.0049 (10)	0.0116 (9)	0.0191 (10)
C14	0.0526 (12)	0.0477 (11)	0.0445 (10)	−0.0078 (9)	−0.0049 (9)	0.0098 (9)
C15	0.0538 (11)	0.0414 (10)	0.0342 (9)	0.0028 (9)	0.0000 (8)	0.0044 (8)
C16	0.0791 (16)	0.0780 (16)	0.0635 (14)	0.0081 (13)	−0.0036 (12)	0.0300 (12)
C17	0.0606 (13)	0.0582 (12)	0.0463 (11)	−0.0009 (10)	0.0139 (10)	0.0102 (9)

Geometric parameters (Å, º) top

Cl1—C1	1.7511 (15)	C11—C12	1.335 (3)
O1—C15	1.237 (2)	C12—C13	1.405 (3)
N1—C1	1.294 (2)	C13—C14	1.342 (3)
N1—C8	1.372 (2)	C14—C15	1.429 (3)
N2—C10	1.463 (3)	C3—H3	0.9300
N2—C11	1.372 (2)	C4—H4	0.9300
N2—C15	1.390 (2)	C5—H5	0.9300
C1—C2	1.411 (2)	C10—H10A	0.9700
C2—C3	1.365 (2)	C10—H10B	0.9700
C2—C10	1.511 (3)	C11—H11	0.9300
C3—C9	1.415 (2)	C12—H12	0.9300
C4—C5	1.360 (3)	C13—H13	0.9300
C4—C9	1.407 (2)	C14—H14	0.9300
C5—C6	1.409 (3)	C16—H16A	0.9600
C6—C7	1.382 (3)	C16—H16B	0.9600
C6—C16	1.517 (3)	C16—H16C	0.9600
C7—C8	1.423 (2)	C17—H17A	0.9600
C7—C17	1.512 (3)	C17—H17B	0.9600
C8—C9	1.415 (2)	C17—H17C	0.9600

Cl1···C3ⁱ	3.6175 (15)	C11···H3	3.0500
Cl1···C14ⁱ	3.324 (2)	C15···H17A^v	2.9400
Cl1···C15ⁱ	3.468 (2)	C16···H17A	3.0500
Cl1···H3ⁱ	3.0300	C16···H17C	2.7500
Cl1···H10A	2.6700	C17···H16A	2.8500
Cl1···H10B	3.0400	C17···H16C	2.9400
Cl1···H12ⁱⁱ	3.1000	H3···Cl1^vi	3.0300
Cl1···H13ⁱⁱ	3.0100	H3···N2	2.6000
O1···C2	3.140 (2)	H3···C11	3.0500
O1···C12ⁱⁱⁱ	3.318 (2)	H3···H4	2.5300
O1···H10A	2.4700	H4···H3	2.5300
O1···H17C^iv	2.7000	H4···H4^viii	2.5800
O1···H12ⁱⁱⁱ	2.5200	H5···H16B	2.3200
O1···H17A^v	2.7100	H10A···Cl1	2.6700
N1···H17B	2.3800	H10A···O1	2.4700
N2···H3	2.6000	H10B···Cl1	3.0400
C2···O1	3.140 (2)	H10B···H11	2.2900
C3···Cl1^vi	3.6175 (15)	H10B···C5^vii	3.0200
C3···C11	3.595 (2)	H11···H10B	2.2900
C3···C15	3.427 (2)	H11···C6^vii	3.0100
C4···C13ⁱⁱⁱ	3.495 (3)	H11···C7^vii	3.0400
C6···C14ⁱⁱⁱ	3.394 (3)	H11···H16A^vii	2.4600
C7···C14ⁱⁱⁱ	3.543 (3)	H11···H17C^vii	2.5000
C7···C15ⁱⁱⁱ	3.546 (2)	H12···Cl1^ix	3.1000
C9···C13ⁱⁱⁱ	3.513 (2)	H12···O1^v	2.5200
C9···C12ⁱⁱⁱ	3.586 (3)	H13···Cl1^ix	3.0100
C11···C3	3.595 (2)	H16A···C17	2.8500
C12···O1^v	3.318 (2)	H16A···H17C	2.3400
C12···C9^v	3.586 (3)	H16A···H11^vii	2.4600
C13···C9^v	3.513 (2)	H16B···H5	2.3200
C13···C4^v	3.495 (3)	H16C···C17	2.9400
C14···C6^v	3.394 (3)	H17A···C16	3.0500
C14···C7^v	3.543 (3)	H17A···O1ⁱⁱⁱ	2.7100
C14···Cl1^vi	3.324 (2)	H17A···C15ⁱⁱⁱ	2.9400
C15···C3	3.427 (2)	H17B···N1	2.3800
C15···C7^v	3.546 (2)	H17C···C16	2.7500
C15···Cl1^vi	3.468 (2)	H17C···H16A	2.3400
C5···H10B^vii	3.0200	H17C···O1^x	2.7000
C6···H11^vii	3.0100	H17C···H11^vii	2.5000
C7···H11^vii	3.0400

C1—N1—C8	117.44 (13)	N2—C15—C14	114.82 (15)
C10—N2—C11	120.11 (15)	C2—C3—H3	119.00
C10—N2—C15	117.76 (14)	C9—C3—H3	120.00
C11—N2—C15	122.06 (15)	C5—C4—H4	120.00
Cl1—C1—N1	115.48 (12)	C9—C4—H4	120.00
Cl1—C1—C2	117.13 (12)	C4—C5—H5	119.00
N1—C1—C2	127.38 (14)	C6—C5—H5	119.00
C1—C2—C3	115.09 (15)	N2—C10—H10A	109.00
C1—C2—C10	120.33 (14)	N2—C10—H10B	109.00
C3—C2—C10	124.58 (15)	C2—C10—H10A	109.00
C2—C3—C9	120.99 (14)	C2—C10—H10B	109.00
C5—C4—C9	119.53 (16)	H10A—C10—H10B	108.00
C4—C5—C6	122.27 (18)	N2—C11—H11	119.00
C5—C6—C7	120.08 (17)	C12—C11—H11	119.00
C5—C6—C16	119.16 (18)	C11—C12—H12	121.00
C7—C6—C16	120.68 (17)	C13—C12—H12	121.00
C6—C7—C8	118.09 (15)	C12—C13—H13	120.00
C6—C7—C17	122.09 (16)	C14—C13—H13	120.00
C8—C7—C17	119.79 (14)	C13—C14—H14	119.00
N1—C8—C7	118.03 (13)	C15—C14—H14	119.00
N1—C8—C9	120.77 (14)	C6—C16—H16A	110.00
C7—C8—C9	121.19 (13)	C6—C16—H16B	109.00
C3—C9—C4	123.20 (14)	C6—C16—H16C	110.00
C3—C9—C8	118.04 (13)	H16A—C16—H16B	109.00
C4—C9—C8	118.71 (14)	H16A—C16—H16C	109.00
N2—C10—C2	113.49 (15)	H16B—C16—H16C	109.00
N2—C11—C12	121.90 (18)	C7—C17—H17A	109.00
C11—C12—C13	118.58 (18)	C7—C17—H17B	109.00
C12—C13—C14	120.33 (19)	C7—C17—H17C	109.00
C13—C14—C15	122.32 (18)	H17A—C17—H17B	110.00
O1—C15—N2	119.46 (18)	H17A—C17—H17C	109.00
O1—C15—C14	125.72 (17)	H17B—C17—H17C	109.00

C8—N1—C1—Cl1	−177.63 (11)	C9—C4—C5—C6	1.4 (3)
C8—N1—C1—C2	1.3 (2)	C5—C4—C9—C8	1.9 (2)
C1—N1—C8—C7	−175.25 (15)	C5—C4—C9—C3	−175.64 (16)
C1—N1—C8—C9	3.7 (2)	C4—C5—C6—C7	−3.3 (3)
C10—N2—C11—C12	−177.86 (18)	C4—C5—C6—C16	173.50 (18)
C11—N2—C15—C14	0.5 (2)	C16—C6—C7—C17	2.7 (3)
C10—N2—C15—O1	−2.8 (2)	C5—C6—C7—C8	1.6 (3)
C15—N2—C11—C12	−0.9 (3)	C5—C6—C7—C17	179.44 (17)
C11—N2—C15—O1	−179.78 (17)	C16—C6—C7—C8	−175.12 (16)
C10—N2—C15—C14	177.47 (16)	C6—C7—C8—C9	1.7 (2)
C11—N2—C10—C2	−104.43 (18)	C17—C7—C8—N1	2.8 (2)
C15—N2—C10—C2	78.5 (2)	C6—C7—C8—N1	−179.28 (15)
N1—C1—C2—C3	−5.0 (3)	C17—C7—C8—C9	−176.16 (15)
N1—C1—C2—C10	174.62 (16)	C7—C8—C9—C4	−3.5 (2)
Cl1—C1—C2—C10	−6.5 (2)	C7—C8—C9—C3	174.16 (15)
Cl1—C1—C2—C3	173.96 (12)	N1—C8—C9—C4	177.54 (15)
C1—C2—C3—C9	3.5 (2)	N1—C8—C9—C3	−4.8 (2)
C1—C2—C10—N2	−161.79 (15)	N2—C11—C12—C13	0.7 (3)
C3—C2—C10—N2	17.8 (2)	C11—C12—C13—C14	−0.2 (3)
C10—C2—C3—C9	−176.05 (16)	C12—C13—C14—C15	−0.3 (3)
C2—C3—C9—C4	178.47 (16)	C13—C14—C15—O1	−179.63 (19)
C2—C3—C9—C8	0.9 (2)	C13—C14—C15—N2	0.1 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2	0.93	2.60	2.902 (2)	100
C10—H10A···Cl1	0.97	2.67	2.987 (2)	100
C12—H12···O1^v	0.93	2.52	3.318 (2)	143
C17—H17B···N1	0.96	2.38	2.821 (2)	108

Symmetry code: (v) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClN₂O
M_r	298.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.07034 (17), 15.4729 (4), 13.1704 (3)
β (°)	96.342 (2)
V (Å³)	1432.01 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.24 × 0.15 × 0.12

Data collection
Diffractometer	Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.953, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	15150, 2810, 2008
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.06
No. of reflections	2810
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2	0.93	2.60	2.902 (2)	100
C10—H10A···Cl1	0.97	2.67	2.987 (2)	100
C12—H12···O1ⁱ	0.93	2.52	3.318 (2)	143
C17—H17B···N1	0.96	2.38	2.821 (2)	108

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

References

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