2-Chloro-7-methyl-12-phenyldibenzo[b,g][1,8]naphthyridin-11(6H)-one

Vennila, K.N.; Prabha, K.; Manoj, M.; Prasad, K.J.R.; Velmurugan, D.

doi:10.1107/S160053681002430X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1823

doi:10.1107/S160053681002430X

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2-Chloro-7-methyl-12-phenyldibenzo[b,g][1,8]naphthyridin-11(6H)-one

K. N. Vennila,^a K. Prabha,^b M. Manoj,^b K. J. Rajendra Prasad ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 3 June 2010; accepted 22 June 2010; online 26 June 2010)

In the title compound, C₂₃H₁₅ClN₂O, the fused ring system is planar: the deviation of all the non-H atoms from the plane through all four fused rings is less than 0.31 Å. The plane of the phenyl ring is inclined at 71.78 (5)° to the mean plane of the 1,8-naphthrydine ring system. The crystal structure is devoid of any classical hydrogen bonds but π–π interactions are present.

Related literature

For the biological activity of [1,8]naphthyridine derivatives, see: Egawa et al. (1984 ); Cooper et al. (1992 ); Chen et al. (1997); Balin & Tan (1984 ); Nadaraj et al. (2009 ); Kuroda et al. (1992 ). For the synthesis of the title compound, see: Manoj et al. (2009 ). For the crystal structures of other naphthrydine derivatives, see: Sivakumar et al. (2003 ); Seebacher et al. (2010 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₁₅ClN₂O
M_r = 370.82
Triclinic, $[P \overline 1]$
a = 8.2434 (2) Å
b = 8.5528 (2) Å
c = 13.0740 (3) Å
α = 89.446 (1)°
β = 74.362 (1)°
γ = 77.672 (1)°
V = 866.06 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.25 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.943, T_max = 0.947
21083 measured reflections
5019 independent reflections
4047 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.138
S = 1.00
5019 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
π–π interactions (Å).

Cg1–Cg4 are the centroids of the N1/C5–C9, N2/C8–C12, C1–C6 and C10—C16 rings, respectively.

Cg1⋯Cg2ⁱ	3.7936 (6)
Cg1⋯Cg4ⁱⁱ	3.7721 (7)
Cg2⋯Cg1ⁱ	3.7935 (6)
Cg2⋯Cg2ⁱⁱ	3.6542 (6)
Cg2⋯Cg3ⁱ	3.8725 (7)
Cg2⋯Cg4ⁱⁱ	3.5506 (7)
Cg3⋯Cg2ⁱ	3.8725 (7)
Cg3⋯Cg4ⁱⁱ	3.6485 (8)
Symmetry codes: (i) −x + 2, −y + 1, −z; (ii) −x + 2, −y, −z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002430X/su2185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002430X/su2185Isup2.hkl

checkCIF report

Comment top

In general, nitrogen containing heterocyclic compounds play important roles in biological activities. Among such compounds, [1,8]naphthyridine derivatives represent the most active class of compounds possessing a wide spectrum of biological activities, such as antibacterial (Miyamoto et al., 1984, Cooper et al., 1992), antitumour (Chen et al., 1997), antimalarial (Balin et al., 1984), antifungal (Nadaraj et al., 2009), anti-inflammatory (Kuroda et al., 1992), antihypertensive activities etc. This paper describes the crystal structure of the title compound, which will help us in our studies on drug design.

The title compound consists of a [1,8]napthyridine core with methyl, chloro-phenyl and phenyl group substituents (Fig. 1). The dihedral angle between the two fused rings of the napthyridine moiety is found to be 3.08 (3)°, indicating that it is almost planar. The phenyl ring is inclined to the mean plane of the [1,8]naphthrydine ring system by 72.51 (3)°. The bond lengths of the formal single bonds, and C2—Cl1 = 1.7392 (14) and C12–O1 = 1.2240 (14) Å, are in normal ranges (Allen et al., 1987), and similar to those observed in other naphthrydine derivatives (Sivakumar et al., 2003; Seebacher et al., 2010).

The crystal packing of the molecules in the crystal is influenced by π–π interactions and van der Waals forces (Fig. 2 and Table 1).

Footnote for Table 1: Symmetry codes : (i) -x+2, -y+1, -z; (ii) -x+2, -y, -z.

Related literature top

For the biological activity of [1,8]naphthyridine derivatives, see: Miyamoto et al. (1984); Cooper et al. (1992); Chen et al. (1997); Balin et al. (1984); Nadaraj et al. (2009); Kuroda et al. (1992). For the synthesis of the title compound, see: Manoj et al. (2009). For the crystal structures of other naphthrydine derivatives, see: Sivakumar et al. (2003); Seebacher et al. (2010). For bond-length data, see: Allen et al. (1987). For related literatur [on what subject?], see: Egawa et al. (1984).

Experimental top

The title compund was synthesized according to the published procedure (Manoj et al., 2009). 2[(2'-Benzoyl-4'-chlorophenyl)amino]-4-chloroquinoline (2 mmol) was added to polyphosphoric acid (6 g of P₂O₅ in 3 ml of H₃PO₄) and heated at 478–483 K for 5 h. The reaction was monitored by using TLC. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. It was then purified by column chromatography using silica gel and the product eluted with a petroleum ether:ethyl acetate (96:4) mixture, to give the title compound as a pale yellow solid. It was recrystallized using methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule, showing the thermal ellipsoids drawn at the 50% probability level.
	Fig. 2. View of the crystal packing of the title compound, illustrating the π–π interactions as dotted lines [the centroids are marked by large black dots; see Table 1 for details].

2-Chloro-7-methyl-12-phenyldibenzo[b,g][1,8]naphthyridin- 11(6H)-one top

Crystal data top

C₂₃H₁₅ClN₂O	Z = 2
M_r = 370.82	F(000) = 384
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2434 (2) Å	Cell parameters from 5019 reflections
b = 8.5528 (2) Å	θ = 1.6–30.0°
c = 13.0740 (3) Å	µ = 0.24 mm⁻¹
α = 89.446 (1)°	T = 293 K
β = 74.362 (1)°	Block, pale yellow
γ = 77.672 (1)°	0.25 × 0.24 × 0.23 mm
V = 866.06 (4) Å³

Data collection top

Bruker SMART APEXII area-detector diffractometer	5019 independent reflections
Radiation source: fine-focus sealed tube	4047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 30.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.943, T_max = 0.947	k = −12→12
21083 measured reflections	l = −17→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0812P)² + 0.1735P] where P = (F_o² + 2F_c²)/3
5019 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₁₅ClN₂O	γ = 77.672 (1)°
M_r = 370.82	V = 866.06 (4) Å³
Triclinic, P1	Z = 2
a = 8.2434 (2) Å	Mo Kα radiation
b = 8.5528 (2) Å	µ = 0.24 mm⁻¹
c = 13.0740 (3) Å	T = 293 K
α = 89.446 (1)°	0.25 × 0.24 × 0.23 mm
β = 74.362 (1)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	5019 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4047 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.947	R_int = 0.025
21083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
5019 reflections	Δρ_min = −0.35 e Å⁻³
245 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 > 2sigma(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	0.43107 (6)	0.82442 (6)	0.41605 (3)	0.06692 (16)
C8	0.97978 (14)	0.28540 (13)	0.08976 (9)	0.0295 (2)
N1	0.75659 (13)	0.43848 (12)	0.01596 (8)	0.0347 (2)
C6	0.75767 (14)	0.49589 (13)	0.19809 (9)	0.0321 (2)
C7	0.91173 (14)	0.37615 (13)	0.18528 (9)	0.0303 (2)
C11	1.19508 (14)	0.07433 (13)	−0.03719 (9)	0.0318 (2)
N2	0.96411 (13)	0.24442 (12)	−0.08970 (8)	0.0349 (2)
H2	0.9104	0.2694	−0.1376	0.042*
C5	0.68564 (14)	0.52218 (14)	0.11069 (9)	0.0329 (2)
C9	0.89694 (14)	0.32538 (13)	0.00739 (9)	0.0298 (2)
O1	1.18861 (13)	0.08963 (12)	0.14332 (7)	0.0456 (2)
C16	1.17758 (17)	0.05651 (15)	−0.22018 (10)	0.0375 (3)
C12	1.12754 (15)	0.14578 (14)	0.07187 (9)	0.0318 (2)
C10	1.11201 (14)	0.12564 (13)	−0.11549 (9)	0.0317 (2)
C15	1.32690 (18)	−0.06129 (16)	−0.24169 (11)	0.0443 (3)
H15	1.3730	−0.1075	−0.3103	0.053*
C19	1.15161 (16)	0.40958 (15)	0.25824 (10)	0.0390 (3)
H19	1.1985	0.4551	0.1953	0.047*
C18	0.99944 (15)	0.35745 (14)	0.27169 (9)	0.0334 (2)
C13	1.34488 (16)	−0.04709 (15)	−0.06305 (11)	0.0392 (3)
H13	1.3998	−0.0829	−0.0110	0.047*
C1	0.67473 (16)	0.59156 (15)	0.29368 (10)	0.0388 (3)
H1	0.7190	0.5754	0.3522	0.047*
C4	0.53475 (16)	0.64433 (16)	0.12077 (12)	0.0423 (3)
H4	0.4868	0.6619	0.0638	0.051*
C23	0.92949 (19)	0.29264 (18)	0.36673 (11)	0.0451 (3)
H23	0.8252	0.2611	0.3775	0.054*
C17	1.0871 (2)	0.11093 (18)	−0.30353 (10)	0.0472 (3)
H17A	1.1601	0.0680	−0.3721	0.071*
H17B	1.0616	0.2259	−0.3030	0.071*
H17C	0.9815	0.0738	−0.2890	0.071*
C2	0.53032 (17)	0.70682 (16)	0.29904 (11)	0.0424 (3)
C20	1.23394 (19)	0.39418 (18)	0.33819 (12)	0.0494 (3)
H20	1.3351	0.4308	0.3293	0.059*
C21	1.1663 (2)	0.3246 (2)	0.43107 (12)	0.0584 (4)
H21	1.2237	0.3114	0.4839	0.070*
C14	1.41133 (18)	−0.11368 (17)	−0.16453 (12)	0.0465 (3)
H14	1.5121	−0.1933	−0.1818	0.056*
C22	1.0139 (2)	0.2747 (2)	0.44566 (12)	0.0584 (4)
H22	0.9678	0.2288	0.5086	0.070*
C3	0.45924 (17)	0.73618 (17)	0.21266 (13)	0.0468 (3)
H3	0.3618	0.8174	0.2181	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0572 (2)	0.0680 (3)	0.0571 (2)	0.00139 (19)	0.00421 (18)	−0.01642 (19)
C8	0.0295 (5)	0.0310 (5)	0.0304 (5)	−0.0063 (4)	−0.0127 (4)	0.0058 (4)
N1	0.0342 (5)	0.0353 (5)	0.0368 (5)	−0.0039 (4)	−0.0166 (4)	0.0056 (4)
C6	0.0303 (5)	0.0321 (5)	0.0349 (5)	−0.0068 (4)	−0.0106 (4)	0.0034 (4)
C7	0.0309 (5)	0.0330 (5)	0.0305 (5)	−0.0087 (4)	−0.0130 (4)	0.0063 (4)
C11	0.0307 (5)	0.0314 (5)	0.0345 (5)	−0.0076 (4)	−0.0103 (4)	0.0035 (4)
N2	0.0372 (5)	0.0389 (5)	0.0299 (5)	−0.0033 (4)	−0.0155 (4)	0.0034 (4)
C5	0.0309 (5)	0.0322 (5)	0.0382 (6)	−0.0067 (4)	−0.0140 (4)	0.0053 (4)
C9	0.0318 (5)	0.0313 (5)	0.0298 (5)	−0.0080 (4)	−0.0133 (4)	0.0066 (4)
O1	0.0491 (5)	0.0473 (5)	0.0404 (5)	0.0056 (4)	−0.0247 (4)	0.0027 (4)
C16	0.0418 (6)	0.0399 (6)	0.0325 (6)	−0.0139 (5)	−0.0091 (5)	0.0031 (4)
C12	0.0315 (5)	0.0326 (5)	0.0340 (5)	−0.0059 (4)	−0.0143 (4)	0.0053 (4)
C10	0.0320 (5)	0.0317 (5)	0.0324 (5)	−0.0092 (4)	−0.0091 (4)	0.0041 (4)
C15	0.0437 (7)	0.0443 (7)	0.0405 (6)	−0.0096 (5)	−0.0038 (5)	−0.0056 (5)
C19	0.0381 (6)	0.0406 (6)	0.0405 (6)	−0.0065 (5)	−0.0159 (5)	0.0020 (5)
C18	0.0359 (5)	0.0350 (5)	0.0305 (5)	−0.0035 (4)	−0.0144 (4)	0.0003 (4)
C13	0.0341 (6)	0.0363 (6)	0.0474 (7)	−0.0034 (4)	−0.0147 (5)	0.0014 (5)
C1	0.0369 (6)	0.0410 (6)	0.0377 (6)	−0.0077 (5)	−0.0092 (5)	−0.0008 (5)
C4	0.0352 (6)	0.0403 (6)	0.0525 (7)	−0.0018 (5)	−0.0190 (5)	0.0055 (5)
C23	0.0489 (7)	0.0552 (8)	0.0357 (6)	−0.0156 (6)	−0.0161 (5)	0.0082 (5)
C17	0.0581 (8)	0.0523 (7)	0.0315 (6)	−0.0100 (6)	−0.0144 (6)	0.0013 (5)
C2	0.0353 (6)	0.0403 (6)	0.0466 (7)	−0.0070 (5)	−0.0033 (5)	−0.0034 (5)
C20	0.0447 (7)	0.0542 (8)	0.0553 (8)	−0.0081 (6)	−0.0259 (6)	−0.0069 (6)
C21	0.0677 (10)	0.0708 (10)	0.0445 (8)	−0.0060 (8)	−0.0353 (7)	−0.0027 (7)
C14	0.0369 (6)	0.0438 (7)	0.0534 (8)	−0.0012 (5)	−0.0088 (6)	−0.0056 (6)
C22	0.0709 (10)	0.0748 (11)	0.0352 (7)	−0.0160 (8)	−0.0242 (7)	0.0126 (7)
C3	0.0319 (6)	0.0414 (7)	0.0624 (9)	−0.0008 (5)	−0.0106 (6)	0.0006 (6)

Geometric parameters (Å, º) top

Cl1—C2	1.7392 (14)	C19—C20	1.3828 (18)
C8—C7	1.3899 (15)	C19—C18	1.3863 (17)
C8—C9	1.4256 (14)	C19—H19	0.9300
C8—C12	1.4816 (15)	C18—C23	1.3859 (18)
N1—C9	1.3196 (14)	C13—C14	1.3690 (19)
N1—C5	1.3551 (15)	C13—H13	0.9300
C6—C5	1.4187 (16)	C1—C2	1.3598 (18)
C6—C1	1.4210 (16)	C1—H1	0.9300
C6—C7	1.4223 (15)	C4—C3	1.362 (2)
C7—C18	1.4873 (15)	C4—H4	0.9300
C11—C10	1.3965 (16)	C23—C22	1.3824 (19)
C11—C13	1.3971 (16)	C23—H23	0.9300
C11—C12	1.4697 (16)	C17—H17A	0.9600
N2—C9	1.3681 (15)	C17—H17B	0.9600
N2—C10	1.3741 (15)	C17—H17C	0.9600
N2—H2	0.8600	C2—C3	1.404 (2)
C5—C4	1.4197 (16)	C20—C21	1.379 (2)
O1—C12	1.2240 (14)	C20—H20	0.9300
C16—C15	1.3780 (18)	C21—C22	1.376 (2)
C16—C10	1.4126 (16)	C21—H21	0.9300
C16—C17	1.4970 (18)	C14—H14	0.9300
C15—C14	1.393 (2)	C22—H22	0.9300
C15—H15	0.9300	C3—H3	0.9300

C7—C8—C9	117.71 (10)	C23—C18—C7	121.22 (11)
C7—C8—C12	123.22 (9)	C19—C18—C7	119.52 (10)
C9—C8—C12	119.00 (10)	C14—C13—C11	120.42 (12)
C9—N1—C5	117.25 (10)	C14—C13—H13	119.8
C5—C6—C1	118.78 (10)	C11—C13—H13	119.8
C5—C6—C7	118.27 (10)	C2—C1—C6	119.61 (12)
C1—C6—C7	122.95 (10)	C2—C1—H1	120.2
C8—C7—C6	118.53 (10)	C6—C1—H1	120.2
C8—C7—C18	122.12 (10)	C3—C4—C5	120.95 (12)
C6—C7—C18	119.28 (10)	C3—C4—H4	119.5
C10—C11—C13	119.38 (11)	C5—C4—H4	119.5
C10—C11—C12	121.14 (10)	C22—C23—C18	120.35 (13)
C13—C11—C12	119.48 (11)	C22—C23—H23	119.8
C9—N2—C10	124.08 (10)	C18—C23—H23	119.8
C9—N2—H2	118.0	C16—C17—H17A	109.5
C10—N2—H2	118.0	C16—C17—H17B	109.5
N1—C5—C6	123.07 (10)	H17A—C17—H17B	109.5
N1—C5—C4	117.74 (11)	C16—C17—H17C	109.5
C6—C5—C4	119.16 (11)	H17A—C17—H17C	109.5
N1—C9—N2	115.15 (10)	H17B—C17—H17C	109.5
N1—C9—C8	125.05 (10)	C1—C2—C3	122.28 (12)
N2—C9—C8	119.80 (10)	C1—C2—Cl1	119.20 (11)
C15—C16—C10	117.34 (11)	C3—C2—Cl1	118.51 (10)
C15—C16—C17	122.02 (12)	C21—C20—C19	120.08 (13)
C10—C16—C17	120.64 (11)	C21—C20—H20	120.0
O1—C12—C11	121.25 (11)	C19—C20—H20	120.0
O1—C12—C8	122.72 (11)	C22—C21—C20	120.06 (13)
C11—C12—C8	116.02 (9)	C22—C21—H21	120.0
N2—C10—C11	119.27 (10)	C20—C21—H21	120.0
N2—C10—C16	119.86 (11)	C13—C14—C15	119.50 (12)
C11—C10—C16	120.87 (11)	C13—C14—H14	120.3
C16—C15—C14	122.47 (12)	C15—C14—H14	120.3
C16—C15—H15	118.8	C21—C22—C23	120.02 (14)
C14—C15—H15	118.8	C21—C22—H22	120.0
C20—C19—C18	120.20 (13)	C23—C22—H22	120.0
C20—C19—H19	119.9	C4—C3—C2	119.20 (12)
C18—C19—H19	119.9	C4—C3—H3	120.4
C23—C18—C19	119.24 (11)	C2—C3—H3	120.4

C9—C8—C7—C6	4.14 (15)	C13—C11—C10—C16	−0.06 (17)
C12—C8—C7—C6	−172.83 (10)	C12—C11—C10—C16	179.99 (10)
C9—C8—C7—C18	−172.72 (10)	C15—C16—C10—N2	179.56 (11)
C12—C8—C7—C18	10.31 (17)	C17—C16—C10—N2	−0.24 (17)
C5—C6—C7—C8	−3.06 (16)	C15—C16—C10—C11	−0.77 (17)
C1—C6—C7—C8	177.96 (10)	C17—C16—C10—C11	179.43 (11)
C5—C6—C7—C18	173.90 (10)	C10—C16—C15—C14	0.73 (19)
C1—C6—C7—C18	−5.09 (17)	C17—C16—C15—C14	−179.47 (13)
C9—N1—C5—C6	1.61 (17)	C20—C19—C18—C23	1.18 (19)
C9—N1—C5—C4	179.91 (10)	C20—C19—C18—C7	179.49 (12)
C1—C6—C5—N1	179.14 (11)	C8—C7—C18—C23	−111.25 (14)
C7—C6—C5—N1	0.11 (17)	C6—C7—C18—C23	71.91 (15)
C1—C6—C5—C4	0.86 (17)	C8—C7—C18—C19	70.48 (15)
C7—C6—C5—C4	−178.16 (10)	C6—C7—C18—C19	−106.37 (13)
C5—N1—C9—N2	−179.86 (10)	C10—C11—C13—C14	0.97 (19)
C5—N1—C9—C8	−0.39 (17)	C12—C11—C13—C14	−179.07 (11)
C10—N2—C9—N1	178.18 (10)	C5—C6—C1—C2	−0.80 (18)
C10—N2—C9—C8	−1.32 (17)	C7—C6—C1—C2	178.18 (11)
C7—C8—C9—N1	−2.55 (17)	N1—C5—C4—C3	−178.17 (12)
C12—C8—C9—N1	174.55 (10)	C6—C5—C4—C3	0.19 (19)
C7—C8—C9—N2	176.90 (10)	C19—C18—C23—C22	−2.4 (2)
C12—C8—C9—N2	−6.00 (16)	C7—C18—C23—C22	179.30 (13)
C10—C11—C12—O1	171.91 (11)	C6—C1—C2—C3	−0.3 (2)
C13—C11—C12—O1	−8.05 (17)	C6—C1—C2—Cl1	−179.41 (9)
C10—C11—C12—C8	−6.49 (16)	C18—C19—C20—C21	1.0 (2)
C13—C11—C12—C8	173.55 (10)	C19—C20—C21—C22	−1.9 (2)
C7—C8—C12—O1	8.09 (18)	C11—C13—C14—C15	−1.0 (2)
C9—C8—C12—O1	−168.84 (11)	C16—C15—C14—C13	0.2 (2)
C7—C8—C12—C11	−173.54 (10)	C20—C21—C22—C23	0.7 (3)
C9—C8—C12—C11	9.53 (15)	C18—C23—C22—C21	1.5 (2)
C9—N2—C10—C11	4.61 (17)	C5—C4—C3—C2	−1.3 (2)
C9—N2—C10—C16	−175.71 (10)	C1—C2—C3—C4	1.4 (2)
C13—C11—C10—N2	179.62 (11)	Cl1—C2—C3—C4	−179.52 (11)
C12—C11—C10—N2	−0.34 (17)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅ClN₂O
M_r	370.82
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2434 (2), 8.5528 (2), 13.0740 (3)
α, β, γ (°)	89.446 (1), 74.362 (1), 77.672 (1)
V (Å³)	866.06 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.943, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	21083, 5019, 4047
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.138, 1.00
No. of reflections	5019
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

π–π interactions (Å). Cg1–Cg4 are the centroids of rings N1/C5–C9, N2/C8–C12, C1–C6 and C10-C16, respectively. top

Cg1–Cg4 are the centroids of the N1/C5–C9, N2/C8–C12, C1–C6 and C10-C16 rings, respectively.

Cg1···Cg2ⁱ	3.7936 (6)
Cg1···Cg4ⁱⁱ	3.7721 (7)
Cg2···Cg1ⁱ	3.7935 (6)
Cg2···Cg2ⁱⁱ	3.6542 (6)
Cg2···Cg3ⁱ	3.8725 (7)
Cg2···Cg4ⁱⁱ	3.5506 (7)
Cg3···Cg2ⁱ	3.8725 (7)
Cg3···Cg4ⁱⁱ	3.6485 (8)

Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y, -z.

Acknowledgements

DV acknowledges the Department of Science and Technology (DST) for providing computing facilities under major research projects and for financial support under the UGC-SAP and DST-FIST programs.

References

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