7-(2-Chloro­phen­yl)-2,6,9-trimethyl­dibenzo[b,h][1,6]naphthyridine

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

doi:10.1107/S1600536810030576

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2426-o2427

https://doi.org/10.1107/S1600536810030576

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7-(2-Chlorophenyl)-2,6,9-trimethyldibenzo[b,h][1,6]naphthyridine

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 13 July 2010; accepted 30 July 2010; online 28 August 2010)

In the title compound, C₂₅H₁₉ClN₂, the dibenzo[b,h][1,6]naphthyridine system is planar to within 0.16 (2) Å, and the chlorophenyl ring is inclined to it by 82.53 (7)°. In the crystal, molecules are linked by C—H⋯N hydrogen bonds, forming chains propagating in [100]. There are also a number of weak π–π stacking interactions present [centroid–centroid distances = 3.8531 (1) and 3.7631 (1) Å].

Related literature

For the biological properties of [1,6]naphthyridine derivatives, see: Zhuang et al. (2003 ); Bedard et al. (2003 ); Hinschberger et al. (2003 ); Naik et al. (2006 ). For the synthesis of the precursor of the title compound, see: Nandha Kumar et al. (2007 ). For the crystal structures of other naphthrydine derivatives, see: Sivakumar et al. (2003 ); Fun et al. (2009 ); Vennila et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₅H₁₉ClN₂
M_r = 382.87
Triclinic, $[P \overline 1]$
a = 6.5575 (4) Å
b = 10.6538 (7) Å
c = 14.3522 (9) Å
α = 93.755 (3)°
β = 103.099 (3)°
γ = 102.074 (3)°
V = 948.25 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.27 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.944, T_max = 0.952
17317 measured reflections
4771 independent reflections
3514 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.143
S = 1.00
4771 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯N7ⁱ	0.93	2.42	3.318 (2)	162
Symmetry code: (i) x-1, 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: https://doi.org/10.1107/S1600536810030576/su2198sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030576/su2198Isup2.hkl

checkCIF report

Comment top

[1,6]naphthyridine derivatives are reported to be a good class of HIV integrase inhibitors (Zhuang et al., 2003). Their antiviral properties have also been reported by (Bedard et al., 2003), and they were proved to be selective antagonists of 5-HT4 receptors (Hinschberger et al., 2003). The planar fused heterocyclic system in the title compound may lead to its DNA intercalating property (Naik et al., 2006). Due to this biological importance, the title compound was chosen for structural studies.

The title compound, illustrated in Fig. 1, consists of a dibenzo[b,h][1,6]naphthyridine core with chlorophenyl and methyl group substitutions. The bond lengths are in normal ranges (Allen et al., 1987), and are similar to those observed for other naphthrydine derivatives (Sivakumar et al., 2003; Fun et al., 2009; Vennila et al., 2010), as are the bond angles. The dihedral angle between the fused ring dibenzo[b,h][1,6]naphthyridine system (N1/N2/C1/C6/C8-C10/C12-C14; planar to within 0.16 (2) Å) and the chlorophenyl ring was found to be 82.53 (7)°. There is an apparent steric clash between the methyl group attached to C8 and the chlorophenyl ring attached to C14. The C9-C8-C19 bond angle of 123.05 (13)° and the C9-C14-C21 bond angle of 124.24 (12)°, suggests that these groups are being forced apart.

The crystal packing is stabilized by C—H···N hydrogen bonds forming chain like patterns propagating along [100] (Table 1, Fig. 2). A number of weak π–π stacking interactions may also stablize the crystal packing (see Table 2 for details).

Related literature top

For the biological properties of [1,6]naphthyridine derivatives, see: Zhuang et al. (2003); Bedard et al. (2003); Hinschberger et al. (2003); Naik et al. (2006). For the synthesis of the precursor of the title compound, see: Nandha Kumar et al. (2007). For the crystal structures of other naphthrydine derivatives, see: Sivakumar et al. (2003); Fun et al. (2009); Vennila et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The precursor of the title compoud, 2,6,4'-trimethyl-4-(N-phenylamino) quinoline, was prepared following the procedure of (Nandha Kumar et al.., 2007). 4-Chloro-2,6-dimethylquinoline (0.002 mol) was reacted with p-toluidine (0.002 mol) under neat conditions at 433 K for 30 mins. The product obtained was washed with water, dried, and purified by column chromatography over silica gel using an ethyl acetate:methanol (95:5) mixture to obtain the product as a white solid. A mixture of 2,6,4'-trimethyl-4-(N-phenylamino) quinoline (0.001 mol) and o-chlorobenzoic acid (0.0011 mol) was added to polyphosphoric acid (1 g of P₂O₅ and 0.5 ml H₃PO₄) and heated at 433 k for 5 h. The reaction mixture was poured into ice water, neutralized with saturated sodium bicarbonate solution to remove the excess of o-chlorobenzoic acid, extracted with ethyl acetate. It was then purified using silica gel column chromatography and the product was eluted with a petroleum ether:ethyl acetate (99:1) mixture to get the final product as a pale yellow solid. Recrystallization using ethanol gave yellow block-like crystals of the title compound suitable for X-ray diffraction analysis.

Structure description top

For the biological properties of [1,6]naphthyridine derivatives, see: Zhuang et al. (2003); Bedard et al. (2003); Hinschberger et al. (2003); Naik et al. (2006). For the synthesis of the precursor of the title compound, see: Nandha Kumar et al. (2007). For the crystal structures of other naphthrydine derivatives, see: Sivakumar et al. (2003); Fun et al. (2009); Vennila et al. (2010). For standard bond lengths, see: Allen et al. (1987).

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 displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The crystal packing of the title compound illustrating the formation of the C-H···N hydrogen bonded (dashed lines) chain propagating along [100], and the π–π interactions (dashed lines); see Tables 1 and 2 for details.

12-(2-chlorophenyl)-2,7,11-trimethyl-5,10-diazatetraphene top

Crystal data top

C₂₅H₁₉ClN₂	Z = 2
M_r = 382.87	F(000) = 400
Triclinic, P1	D_x = 1.341 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5575 (4) Å	Cell parameters from 4797 reflections
b = 10.6538 (7) Å	θ = 1.5–28.5°
c = 14.3522 (9) Å	µ = 0.21 mm⁻¹
α = 93.755 (3)°	T = 293 K
β = 103.099 (3)°	Block, yellow
γ = 102.074 (3)°	0.27 × 0.25 × 0.23 mm
V = 948.25 (10) Å³

Data collection top

Bruker SMART APEXII area-detector diffractometer	4771 independent reflections
Radiation source: fine-focus sealed tube	3514 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scans	θ_max = 28.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.944, T_max = 0.952	k = −14→14
17317 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0694P)² + 0.2763P] where P = (F_o² + 2F_c²)/3
4771 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₅H₁₉ClN₂	γ = 102.074 (3)°
M_r = 382.87	V = 948.25 (10) Å³
Triclinic, P1	Z = 2
a = 6.5575 (4) Å	Mo Kα radiation
b = 10.6538 (7) Å	µ = 0.21 mm⁻¹
c = 14.3522 (9) Å	T = 293 K
α = 93.755 (3)°	0.27 × 0.25 × 0.23 mm
β = 103.099 (3)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	4771 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3514 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.952	R_int = 0.025
17317 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
4771 reflections	Δρ_min = −0.51 e Å⁻³
255 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	Occ. (<1)
Cl1	0.22259 (9)	0.49217 (5)	0.41457 (4)	0.0809 (2)
C9	0.1060 (2)	0.63949 (13)	0.20011 (10)	0.0345 (3)
C14	−0.0361 (2)	0.61889 (13)	0.25997 (11)	0.0354 (3)
N11	0.1756 (2)	0.87266 (11)	0.24184 (9)	0.0396 (3)
C10	0.2149 (2)	0.77063 (13)	0.19709 (10)	0.0353 (3)
C13	−0.0816 (2)	0.72702 (14)	0.30668 (11)	0.0371 (3)
C6	0.3810 (2)	0.79371 (14)	0.14465 (10)	0.0367 (3)
C1	0.4188 (2)	0.68758 (14)	0.09475 (11)	0.0382 (3)
C12	0.0265 (2)	0.85236 (14)	0.29330 (11)	0.0379 (3)
N7	0.2977 (2)	0.56271 (12)	0.09035 (9)	0.0405 (3)
C5	0.5087 (3)	0.91727 (15)	0.14455 (12)	0.0427 (3)
H5	0.4829	0.9885	0.1770	0.051*
C21	−0.1424 (2)	0.48827 (13)	0.28004 (11)	0.0383 (3)
C15	−0.2299 (3)	0.71701 (15)	0.36619 (12)	0.0426 (3)
H15	−0.2983	0.6356	0.3770	0.051*
C2	0.5826 (3)	0.70513 (17)	0.04574 (13)	0.0478 (4)
H2	0.6075	0.6347	0.0119	0.057*
C18	−0.0219 (3)	0.96186 (15)	0.33756 (12)	0.0459 (4)
H18	0.0465	1.0444	0.3289	0.055*
C8	0.1537 (2)	0.53873 (14)	0.13957 (11)	0.0376 (3)
C16	−0.2740 (3)	0.82394 (16)	0.40769 (12)	0.0435 (4)
C4	0.6710 (3)	0.93469 (16)	0.09730 (12)	0.0463 (4)
C26	−0.0401 (3)	0.42446 (15)	0.35054 (12)	0.0450 (4)
C17	−0.1666 (3)	0.94743 (16)	0.39226 (12)	0.0471 (4)
H17	−0.1960	1.0206	0.4204	0.057*
C22	−0.3525 (3)	0.42820 (16)	0.23021 (15)	0.0529 (4)
H22	−0.4273	0.4693	0.1833	0.063*
C3	0.7064 (3)	0.82702 (17)	0.04798 (13)	0.0512 (4)
H3	0.8162	0.8381	0.0160	0.061*
C23	−0.4512 (3)	0.30820 (18)	0.24972 (17)	0.0622 (5)
H23	−0.5900	0.2684	0.2146	0.075*
C19	0.0335 (3)	0.39954 (15)	0.12548 (14)	0.0502 (4)
H19A	0.0790	0.3520	0.0779	0.075*
H19B	−0.1181	0.3942	0.1043	0.075*
H19C	0.0630	0.3635	0.1853	0.075*
C25	−0.1401 (3)	0.30526 (16)	0.37131 (14)	0.0563 (5)
H25	−0.0683	0.2646	0.4195	0.068*
C24	−0.3463 (3)	0.24775 (17)	0.32009 (15)	0.0583 (5)
H24	−0.4144	0.1676	0.3334	0.070*
C20	0.8124 (3)	1.06674 (18)	0.10020 (15)	0.0613 (5)
H20A	0.9161	1.0606	0.0635	0.092*	0.50
H20B	0.8857	1.0999	0.1658	0.092*	0.50
H20C	0.7254	1.1239	0.0732	0.092*	0.50
H20D	0.7687	1.1290	0.1382	0.092*	0.50
H20E	0.7992	1.0897	0.0359	0.092*	0.50
H20F	0.9594	1.0657	0.1284	0.092*	0.50
C27	−0.4337 (3)	0.81378 (19)	0.46916 (15)	0.0603 (5)
H27A	−0.5716	0.8179	0.4303	0.090*
H27B	−0.3858	0.8839	0.5203	0.090*
H27C	−0.4454	0.7331	0.4960	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0751 (4)	0.0620 (3)	0.0805 (4)	−0.0032 (2)	−0.0189 (3)	0.0237 (3)
C9	0.0369 (7)	0.0290 (6)	0.0383 (7)	0.0081 (5)	0.0095 (6)	0.0067 (5)
C14	0.0374 (7)	0.0284 (7)	0.0415 (8)	0.0080 (5)	0.0105 (6)	0.0080 (6)
N11	0.0477 (7)	0.0294 (6)	0.0430 (7)	0.0072 (5)	0.0149 (6)	0.0055 (5)
C10	0.0388 (7)	0.0309 (7)	0.0359 (7)	0.0069 (6)	0.0089 (6)	0.0071 (5)
C13	0.0415 (8)	0.0318 (7)	0.0391 (8)	0.0092 (6)	0.0111 (6)	0.0063 (6)
C6	0.0393 (7)	0.0333 (7)	0.0366 (7)	0.0048 (6)	0.0098 (6)	0.0074 (6)
C1	0.0400 (8)	0.0353 (7)	0.0388 (8)	0.0057 (6)	0.0110 (6)	0.0062 (6)
C12	0.0451 (8)	0.0318 (7)	0.0372 (7)	0.0093 (6)	0.0103 (6)	0.0051 (6)
N7	0.0450 (7)	0.0326 (6)	0.0461 (7)	0.0072 (5)	0.0171 (6)	0.0044 (5)
C5	0.0490 (9)	0.0339 (7)	0.0428 (8)	0.0014 (6)	0.0137 (7)	0.0050 (6)
C21	0.0423 (8)	0.0293 (7)	0.0478 (8)	0.0088 (6)	0.0194 (6)	0.0061 (6)
C15	0.0464 (8)	0.0366 (8)	0.0481 (9)	0.0089 (6)	0.0180 (7)	0.0078 (6)
C2	0.0514 (9)	0.0449 (9)	0.0506 (9)	0.0080 (7)	0.0230 (7)	0.0033 (7)
C18	0.0616 (10)	0.0308 (7)	0.0475 (9)	0.0104 (7)	0.0181 (8)	0.0046 (6)
C8	0.0411 (8)	0.0308 (7)	0.0416 (8)	0.0083 (6)	0.0114 (6)	0.0057 (6)
C16	0.0455 (8)	0.0433 (8)	0.0435 (8)	0.0122 (7)	0.0131 (7)	0.0031 (7)
C4	0.0469 (9)	0.0426 (8)	0.0446 (9)	−0.0026 (7)	0.0128 (7)	0.0081 (7)
C26	0.0552 (9)	0.0343 (7)	0.0445 (9)	0.0064 (7)	0.0134 (7)	0.0069 (6)
C17	0.0599 (10)	0.0380 (8)	0.0470 (9)	0.0170 (7)	0.0165 (8)	0.0001 (7)
C22	0.0446 (9)	0.0416 (9)	0.0728 (12)	0.0090 (7)	0.0142 (8)	0.0142 (8)
C3	0.0487 (9)	0.0539 (10)	0.0520 (10)	0.0013 (7)	0.0239 (8)	0.0071 (8)
C23	0.0433 (9)	0.0473 (10)	0.0937 (15)	−0.0002 (8)	0.0221 (10)	0.0087 (10)
C19	0.0589 (10)	0.0321 (7)	0.0617 (11)	0.0036 (7)	0.0268 (8)	−0.0009 (7)
C25	0.0803 (13)	0.0368 (8)	0.0536 (10)	0.0088 (8)	0.0216 (9)	0.0145 (7)
C24	0.0701 (12)	0.0359 (8)	0.0749 (13)	0.0029 (8)	0.0367 (10)	0.0121 (8)
C20	0.0643 (12)	0.0476 (10)	0.0667 (12)	−0.0099 (8)	0.0265 (10)	0.0076 (9)
C27	0.0630 (11)	0.0554 (11)	0.0694 (12)	0.0128 (9)	0.0334 (10)	−0.0011 (9)

Geometric parameters (Å, º) top

Cl1—C26	1.7342 (18)	C8—C19	1.504 (2)
C9—C14	1.399 (2)	C16—C17	1.413 (2)
C9—C10	1.4381 (19)	C16—C27	1.507 (2)
C9—C8	1.465 (2)	C4—C3	1.397 (2)
C14—C13	1.414 (2)	C4—C20	1.507 (2)
C14—C21	1.4978 (19)	C26—C25	1.386 (2)
N11—C10	1.3272 (18)	C17—H17	0.9300
N11—C12	1.3449 (19)	C22—C23	1.384 (2)
C10—C6	1.448 (2)	C22—H22	0.9300
C13—C12	1.422 (2)	C3—H3	0.9300
C13—C15	1.425 (2)	C23—C24	1.365 (3)
C6—C1	1.395 (2)	C23—H23	0.9300
C6—C5	1.405 (2)	C19—H19A	0.9600
C1—N7	1.3888 (19)	C19—H19B	0.9600
C1—C2	1.399 (2)	C19—H19C	0.9600
C12—C18	1.419 (2)	C25—C24	1.374 (3)
N7—C8	1.2966 (19)	C25—H25	0.9300
C5—C4	1.374 (2)	C24—H24	0.9300
C5—H5	0.9300	C20—H20A	0.9600
C21—C26	1.382 (2)	C20—H20B	0.9600
C21—C22	1.394 (2)	C20—H20C	0.9600
C15—C16	1.365 (2)	C20—H20D	0.9600
C15—H15	0.9300	C20—H20E	0.9600
C2—C3	1.374 (2)	C20—H20F	0.9600
C2—H2	0.9300	C27—H27A	0.9600
C18—C17	1.353 (2)	C27—H27B	0.9600
C18—H18	0.9300	C27—H27C	0.9600

C14—C9—C10	117.59 (12)	C18—C17—H17	119.2
C14—C9—C8	125.62 (13)	C16—C17—H17	119.2
C10—C9—C8	116.79 (13)	C23—C22—C21	120.83 (17)
C9—C14—C13	118.93 (13)	C23—C22—H22	119.6
C9—C14—C21	124.24 (12)	C21—C22—H22	119.6
C13—C14—C21	116.82 (13)	C2—C3—C4	121.42 (15)
C10—N11—C12	118.23 (12)	C2—C3—H3	119.3
N11—C10—C9	123.65 (13)	C4—C3—H3	119.3
N11—C10—C6	117.60 (13)	C24—C23—C22	120.50 (18)
C9—C10—C6	118.73 (12)	C24—C23—H23	119.8
C14—C13—C12	118.07 (13)	C22—C23—H23	119.8
C14—C13—C15	123.54 (13)	C8—C19—H19A	109.5
C12—C13—C15	118.39 (13)	C8—C19—H19B	109.5
C1—C6—C5	119.07 (14)	H19A—C19—H19B	109.5
C1—C6—C10	118.10 (13)	C8—C19—H19C	109.5
C5—C6—C10	122.80 (14)	H19A—C19—H19C	109.5
N7—C1—C6	122.51 (13)	H19B—C19—H19C	109.5
N7—C1—C2	117.55 (13)	C24—C25—C26	119.42 (17)
C6—C1—C2	119.94 (14)	C24—C25—H25	120.3
N11—C12—C18	118.06 (13)	C26—C25—H25	120.3
N11—C12—C13	123.19 (13)	C23—C24—C25	120.02 (16)
C18—C12—C13	118.73 (14)	C23—C24—H24	120.0
C8—N7—C1	120.50 (13)	C25—C24—H24	120.0
C4—C5—C6	121.15 (15)	C4—C20—H20A	109.5
C4—C5—H5	119.4	C4—C20—H20B	109.5
C6—C5—H5	119.4	H20A—C20—H20B	109.5
C26—C21—C22	117.31 (14)	C4—C20—H20C	109.5
C26—C21—C14	121.67 (14)	H20A—C20—H20C	109.5
C22—C21—C14	120.98 (14)	H20B—C20—H20C	109.5
C16—C15—C13	121.68 (15)	C4—C20—H20D	109.5
C16—C15—H15	119.2	H20A—C20—H20D	141.1
C13—C15—H15	119.2	H20B—C20—H20D	56.3
C3—C2—C1	119.59 (15)	H20C—C20—H20D	56.3
C3—C2—H2	120.2	C4—C20—H20E	109.5
C1—C2—H2	120.2	H20A—C20—H20E	56.3
C17—C18—C12	120.70 (15)	H20B—C20—H20E	141.1
C17—C18—H18	119.6	H20C—C20—H20E	56.3
C12—C18—H18	119.6	H20D—C20—H20E	109.5
N7—C8—C9	122.88 (13)	C4—C20—H20F	109.5
N7—C8—C19	114.02 (13)	H20A—C20—H20F	56.3
C9—C8—C19	123.05 (13)	H20B—C20—H20F	56.3
C15—C16—C17	118.83 (15)	H20C—C20—H20F	141.1
C15—C16—C27	121.87 (15)	H20D—C20—H20F	109.5
C17—C16—C27	119.31 (14)	H20E—C20—H20F	109.5
C5—C4—C3	118.82 (15)	C16—C27—H27A	109.5
C5—C4—C20	120.96 (16)	C16—C27—H27B	109.5
C3—C4—C20	120.20 (15)	H27A—C27—H27B	109.5
C21—C26—C25	121.90 (16)	C16—C27—H27C	109.5
C21—C26—Cl1	119.98 (12)	H27A—C27—H27C	109.5
C25—C26—Cl1	118.11 (14)	H27B—C27—H27C	109.5
C18—C17—C16	121.65 (14)

C10—C9—C14—C13	6.1 (2)	C13—C14—C21—C22	82.85 (19)
C8—C9—C14—C13	−173.70 (13)	C14—C13—C15—C16	−178.02 (15)
C10—C9—C14—C21	−172.70 (13)	C12—C13—C15—C16	1.9 (2)
C8—C9—C14—C21	7.5 (2)	N7—C1—C2—C3	179.93 (16)
C12—N11—C10—C9	0.4 (2)	C6—C1—C2—C3	0.6 (3)
C12—N11—C10—C6	−177.97 (13)	N11—C12—C18—C17	−178.30 (15)
C14—C9—C10—N11	−5.4 (2)	C13—C12—C18—C17	0.6 (2)
C8—C9—C10—N11	174.47 (13)	C1—N7—C8—C9	1.4 (2)
C14—C9—C10—C6	172.95 (13)	C1—N7—C8—C19	178.83 (14)
C8—C9—C10—C6	−7.2 (2)	C14—C9—C8—N7	−175.27 (14)
C9—C14—C13—C12	−2.4 (2)	C10—C9—C8—N7	4.9 (2)
C21—C14—C13—C12	176.51 (13)	C14—C9—C8—C19	7.5 (2)
C9—C14—C13—C15	177.54 (14)	C10—C9—C8—C19	−172.28 (14)
C21—C14—C13—C15	−3.6 (2)	C13—C15—C16—C17	−1.1 (2)
N11—C10—C6—C1	−177.95 (13)	C13—C15—C16—C27	178.85 (16)
C9—C10—C6—C1	3.6 (2)	C6—C5—C4—C3	0.6 (3)
N11—C10—C6—C5	4.1 (2)	C6—C5—C4—C20	−177.91 (16)
C9—C10—C6—C5	−174.35 (14)	C22—C21—C26—C25	0.3 (2)
C5—C6—C1—N7	−179.11 (14)	C14—C21—C26—C25	178.09 (15)
C10—C6—C1—N7	2.8 (2)	C22—C21—C26—Cl1	179.19 (13)
C5—C6—C1—C2	0.1 (2)	C14—C21—C26—Cl1	−3.0 (2)
C10—C6—C1—C2	−177.91 (14)	C12—C18—C17—C16	0.2 (3)
C10—N11—C12—C18	−177.28 (14)	C15—C16—C17—C18	0.0 (3)
C10—N11—C12—C13	3.8 (2)	C27—C16—C17—C18	−179.91 (17)
C14—C13—C12—N11	−2.8 (2)	C26—C21—C22—C23	−1.4 (3)
C15—C13—C12—N11	177.25 (14)	C14—C21—C22—C23	−179.24 (16)
C14—C13—C12—C18	178.29 (14)	C1—C2—C3—C4	−0.8 (3)
C15—C13—C12—C18	−1.6 (2)	C5—C4—C3—C2	0.2 (3)
C6—C1—N7—C8	−5.5 (2)	C20—C4—C3—C2	178.72 (18)
C2—C1—N7—C8	175.23 (15)	C21—C22—C23—C24	1.7 (3)
C1—C6—C5—C4	−0.8 (2)	C21—C26—C25—C24	0.6 (3)
C10—C6—C5—C4	177.17 (14)	Cl1—C26—C25—C24	−178.38 (14)
C9—C14—C21—C26	83.9 (2)	C22—C23—C24—C25	−0.9 (3)
C13—C14—C21—C26	−94.89 (17)	C26—C25—C24—C23	−0.3 (3)
C9—C14—C21—C22	−98.31 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N7ⁱ	0.93	2.42	3.318 (2)	162

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉ClN₂
M_r	382.87
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.5575 (4), 10.6538 (7), 14.3522 (9)
α, β, γ (°)	93.755 (3), 103.099 (3), 102.074 (3)
V (Å³)	948.25 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.27 × 0.25 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.944, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	17317, 4771, 3514
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.143, 1.00
No. of reflections	4771
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.51

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N7ⁱ	0.93	2.42	3.318 (2)	162

Symmetry code: (i) x−1, y, z.

π–π interactions [Å]
Cg2 is centroid of ring N11,C9,C10,C12-C14; Cg3 is centroid of ring C1-C6; Cg4 is centroid of ring C12,C13,C15-C18.
Symmetry codes : (i) -1+x, y,z; (ii) 1+x, y,z. top

Cg(I)	Cg(J)	Centroid-to-Centroid
Cg(2)	Cg(3ⁱ)	3.8531 (1)
Cg(3)	Cg(2ⁱⁱ)	3.8531 (1)
Cg(3)	Cg(4ⁱⁱ)	3.7631 (1)
Cg(4)	Cg(3ⁱ)	3.7631 (1)

Acknowledgements

KNV thanks the CSIR for providing a Senior Research Fellowship. DV acknowledges the Department of Science and Technology (DST) for providing data collection facilities under major research projects and is also thankful for the financial support to the Department under UGC–SAP and DST–FIST programs.

References

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