3-[(2-Chloro-6-methyl­quinolin-3-yl)meth­yl]quinazolin-4(3H)-one

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

doi:10.1107/S1600536810020830

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1545

doi:10.1107/S1600536810020830

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3-[(2-Chloro-6-methylquinolin-3-yl)methyl]quinazolin-4(3H)-one

S. Mohana Roopan,^a F. Nawaz Khan,^a Sriramakrishnaswamy Kone,^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 May 2010; accepted 1 June 2010; online 5 June 2010)

In the title molecule, C₁₉H₁₄ClN₃O, the quinoline and quinazoline ring systems form a dihedral angle of 80.75 (4)°. In the crystal, the molecules are linked by pairs of C—H⋯N hydrogen bonds into centrosymmetric dimers, generating R₂²(6) ring motifs. The structure is further stabilized by C—H⋯π interactions and π–π stacking interactions [centroid–centroid distances = 3.7869 (8) and 3.8490 (8) Å].

Related literature

For quinoline analogues, see: Roopan et al. (2009 ); Khan et al. (2009 , 2010a ,b ). For quinazolinone analogues, see: Roopan et al. (2008a ,b ). For the properties and applications of related compounds, see: Abdel-Hamide et al. (1996 ); Bekhit & Khalil (1998 ); Chapman et al. (1963 ); Honda et al. (1979 ).

Experimental

Crystal data

C₁₉H₁₄ClN₃O
M_r = 335.78
Monoclinic, P 2₁ /c
a = 7.86728 (14) Å
b = 14.7098 (3) Å
c = 13.7055 (3) Å
β = 102.1500 (17)°
V = 1550.56 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 K
0.25 × 0.21 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur E CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.938, T_max = 0.960
15755 measured reflections
3048 independent reflections
2417 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.14
3048 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1–C4/C9 and N2/N3/C12/C13/C18/C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯N3ⁱ	0.93	2.51	3.271 (2)	139
C8—H8⋯Cg2ⁱⁱ	0.93	2.89	3.6598 (16)	142
C10—H10A⋯Cg1ⁱⁱⁱ	0.96	2.68	3.5189 (17)	146
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+2.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020830/gk2276sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020830/gk2276Isup2.hkl

checkCIF report

Comment top

Heterocyclic chemistry comprises at least half of all organic chemistry research worldwide (Roopan et al., 2008a,b). In particular, heterocyclic structures form the basis of many pharmaceutical, agrochemical and veterinary products. 4(3H)-quinazolinones and quinolines (Roopan et al., 2009) are classes of fused heterocycles that are of considerable interest because of their biological properties. Some are endowed with antimicrobial, aniconvulsant, antihistamine and anti-inflammatory properties (Abdel-Hamide et al., 1996, Chapman et al., 1963, Bekhit et al., 1998). On the other hand, some quinoline derivatives also have various biological properties like antioxidant, hemolytic and cytotoxicity. These observations prompted us to synthesized heterocyclic compounds containing a quinolinyl-quinazolinone moiety.

As shown in Fig. 1, the quinoline (N1/C1–C9) and quinazoline (N2/N3/C12–C19) ring systems of the title molecule (I) are almost planar with maximum deviations of -0.016 (1) Å for C2 and 0.065 (1) Å for N2, respectively, and there is a dihedral angle of 80.75 (4)° between them.

Two neighbouring molecules are linked by a pair of C—H···N hydrogen bonds into a pseudo-centrosymmetric dimer, generating an R²₂(6) ring motif (Table 1, Fig. 2). In addition, the structure is stabilized by C—H···π interactions (Table 1) and π-π stacking interactions [Cg1···Cg3(2 - x,-y, 2 - z) = 3.7869 (8) Å and Cg3···Cg3(1 - x, -y, 2 - z) = 3.8490 (8) Å; where Cg1 and Cg3 are centroids of the N1/C1–C4/C9 and C4–C9 rings, respectively].

Related literature top

For quinoline analogues, see: Roopan et al. (2009); Khan et al. (2009, 2010a,b). For quinazolinone analogues, see: Roopan et al. (2008a,b). For the properties and applications of related compounds, see: Abdel-Hamide et al. (1996); Bekhit & Khalil (1998); Chapman et al. (1963); Honda et al. (1979).

Experimental top

To a solution of 4(3H)-quinazolinone (146 mg, 1 mmol) in 2 ml of DMF were added KOtBu (112 mg, 1 mmol) in 10 ml of THF and 2-chloro-3-(chloromethyl)-6-methylquinoline (225 mg, 1 mmol) and the resulting mixture was refluxed at 343 K for 1 h. After the completion, the reaction was cooled and the excess of solvent removed under reduced pressure. Crushed ice was mixed with the residue. White solid was formed which was 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 diethyl ether.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (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 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed down a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

3-[(2-Chloro-6-methylquinolin-3-yl)methyl]quinazolin-4(3H)-one top

Crystal data top

C₁₉H₁₄ClN₃O	F(000) = 696
M_r = 335.78	D_x = 1.438 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1326 reflections
a = 7.86728 (14) Å	θ = 2.0–20.7°
b = 14.7098 (3) Å	µ = 0.26 mm⁻¹
c = 13.7055 (3) Å	T = 295 K
β = 102.1500 (17)°	Needle, colourless
V = 1550.56 (5) Å³	0.25 × 0.21 × 0.16 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur E CCD diffractometer	3048 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2417 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→9
T_min = 0.938, T_max = 0.960	k = −18→18
15755 measured reflections	l = −16→16

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0511P)² + 0.0739P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
3048 reflections	Δρ_max = 0.18 e Å⁻³
219 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0123 (15)

Crystal data top

C₁₉H₁₄ClN₃O	V = 1550.56 (5) Å³
M_r = 335.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.86728 (14) Å	µ = 0.26 mm⁻¹
b = 14.7098 (3) Å	T = 295 K
c = 13.7055 (3) Å	0.25 × 0.21 × 0.16 mm
β = 102.1500 (17)°

Data collection top

Oxford Diffraction Xcalibur E CCD diffractometer	3048 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2417 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.960	R_int = 0.026
15755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.14	Δρ_max = 0.18 e Å⁻³
3048 reflections	Δρ_min = −0.19 e Å⁻³
219 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 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	1.05099 (5)	0.28142 (3)	1.12633 (3)	0.0552 (2)
O1	0.60460 (15)	0.24457 (8)	0.79970 (8)	0.0550 (4)
N1	0.90795 (14)	0.12379 (9)	1.13506 (8)	0.0409 (4)
N2	0.82439 (14)	0.32871 (8)	0.89095 (8)	0.0368 (4)
N3	0.79403 (17)	0.48498 (9)	0.92418 (9)	0.0453 (4)
C1	0.94294 (18)	0.18353 (10)	1.07237 (11)	0.0389 (5)
C2	0.90272 (18)	0.17726 (10)	0.96669 (10)	0.0374 (5)
C3	0.82067 (18)	0.09933 (10)	0.92894 (10)	0.0395 (5)
C4	0.77799 (17)	0.03094 (10)	0.99195 (10)	0.0366 (4)
C5	0.69103 (18)	−0.05001 (10)	0.95563 (11)	0.0413 (5)
C6	0.64859 (18)	−0.11435 (10)	1.01883 (11)	0.0403 (5)
C7	0.6946 (2)	−0.09747 (11)	1.12254 (11)	0.0461 (5)
C8	0.77957 (19)	−0.02054 (11)	1.16013 (11)	0.0444 (5)
C9	0.82367 (17)	0.04583 (10)	1.09569 (10)	0.0373 (5)
C10	0.5554 (2)	−0.20015 (11)	0.97943 (13)	0.0519 (6)
C11	0.9436 (2)	0.25093 (11)	0.89857 (12)	0.0442 (5)
C12	0.65169 (19)	0.31653 (10)	0.84072 (10)	0.0383 (4)
C13	0.54199 (18)	0.39518 (10)	0.84513 (10)	0.0376 (5)
C14	0.3617 (2)	0.38997 (12)	0.80976 (11)	0.0497 (6)
C15	0.2604 (2)	0.46424 (15)	0.81376 (12)	0.0613 (7)
C16	0.3351 (3)	0.54611 (15)	0.85043 (13)	0.0658 (7)
C17	0.5113 (2)	0.55297 (12)	0.88491 (12)	0.0571 (6)
C18	0.61654 (19)	0.47690 (10)	0.88456 (10)	0.0406 (5)
C19	0.88460 (19)	0.41208 (11)	0.92637 (11)	0.0415 (5)
H3	0.79220	0.09100	0.86020	0.0470*
H5	0.66180	−0.06000	0.88710	0.0500*
H7	0.66590	−0.14020	1.16640	0.0550*
H8	0.80880	−0.01170	1.22880	0.0530*
H10A	0.44010	−0.19950	0.99230	0.0780*
H10B	0.61780	−0.25170	1.01190	0.0780*
H10C	0.54880	−0.20420	0.90880	0.0780*
H11A	1.06170	0.27200	0.92330	0.0530*
H11B	0.93730	0.22560	0.83250	0.0530*
H14	0.31130	0.33570	0.78350	0.0600*
H15	0.14040	0.46010	0.79180	0.0740*
H16	0.26500	0.59680	0.85160	0.0790*
H17	0.56050	0.60830	0.90850	0.0690*
H19	1.00250	0.41650	0.95480	0.0500*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0554 (3)	0.0545 (3)	0.0522 (3)	−0.0078 (2)	0.0032 (2)	−0.0056 (2)
O1	0.0623 (7)	0.0417 (7)	0.0540 (7)	−0.0106 (5)	−0.0034 (5)	−0.0054 (5)
N1	0.0375 (7)	0.0482 (8)	0.0363 (7)	0.0036 (6)	0.0060 (5)	−0.0013 (6)
N2	0.0353 (6)	0.0375 (7)	0.0368 (6)	−0.0034 (5)	0.0059 (5)	0.0015 (5)
N3	0.0483 (8)	0.0392 (8)	0.0451 (7)	−0.0082 (6)	0.0021 (6)	0.0015 (6)
C1	0.0316 (7)	0.0426 (9)	0.0422 (8)	0.0051 (6)	0.0068 (6)	−0.0016 (7)
C2	0.0347 (8)	0.0412 (9)	0.0377 (8)	0.0094 (6)	0.0110 (6)	0.0016 (6)
C3	0.0442 (8)	0.0435 (9)	0.0320 (7)	0.0103 (7)	0.0109 (6)	−0.0005 (6)
C4	0.0365 (8)	0.0397 (8)	0.0347 (7)	0.0109 (6)	0.0100 (6)	0.0001 (6)
C5	0.0440 (8)	0.0446 (9)	0.0361 (8)	0.0083 (7)	0.0105 (6)	−0.0042 (7)
C6	0.0358 (8)	0.0401 (9)	0.0468 (9)	0.0088 (6)	0.0128 (6)	0.0002 (7)
C7	0.0449 (9)	0.0495 (10)	0.0467 (9)	0.0038 (7)	0.0158 (7)	0.0083 (7)
C8	0.0439 (8)	0.0557 (10)	0.0341 (8)	0.0024 (7)	0.0096 (6)	0.0028 (7)
C9	0.0326 (7)	0.0436 (9)	0.0369 (8)	0.0087 (6)	0.0099 (6)	0.0007 (6)
C10	0.0519 (10)	0.0455 (10)	0.0604 (10)	0.0026 (8)	0.0169 (8)	−0.0015 (8)
C11	0.0436 (9)	0.0479 (9)	0.0436 (8)	0.0035 (7)	0.0152 (7)	0.0017 (7)
C12	0.0430 (8)	0.0383 (8)	0.0317 (7)	−0.0078 (7)	0.0038 (6)	0.0041 (6)
C13	0.0392 (8)	0.0436 (9)	0.0293 (7)	−0.0041 (7)	0.0054 (6)	0.0083 (6)
C14	0.0414 (9)	0.0646 (11)	0.0400 (9)	−0.0059 (8)	0.0015 (7)	0.0123 (8)
C15	0.0433 (10)	0.0941 (15)	0.0460 (10)	0.0117 (10)	0.0084 (7)	0.0210 (10)
C16	0.0701 (13)	0.0799 (14)	0.0482 (10)	0.0341 (11)	0.0143 (9)	0.0114 (10)
C17	0.0739 (12)	0.0484 (10)	0.0478 (10)	0.0125 (9)	0.0101 (8)	0.0022 (8)
C18	0.0475 (9)	0.0425 (9)	0.0318 (7)	−0.0007 (7)	0.0083 (6)	0.0046 (6)
C19	0.0386 (8)	0.0432 (9)	0.0402 (8)	−0.0114 (7)	0.0028 (6)	0.0039 (7)

Geometric parameters (Å, º) top

Cl1—C1	1.7545 (15)	C13—C14	1.401 (2)
O1—C12	1.2191 (19)	C13—C18	1.396 (2)
N1—C1	1.2984 (19)	C14—C15	1.360 (3)
N1—C9	1.3767 (19)	C15—C16	1.387 (3)
N2—C11	1.469 (2)	C16—C17	1.371 (3)
N2—C12	1.3994 (19)	C17—C18	1.393 (2)
N2—C19	1.367 (2)	C3—H3	0.9300
N3—C18	1.393 (2)	C5—H5	0.9300
N3—C19	1.284 (2)	C7—H7	0.9300
C1—C2	1.419 (2)	C8—H8	0.9300
C2—C3	1.363 (2)	C10—H10A	0.9600
C2—C11	1.509 (2)	C10—H10B	0.9600
C3—C4	1.412 (2)	C10—H10C	0.9600
C4—C5	1.411 (2)	C11—H11A	0.9700
C4—C9	1.4084 (19)	C11—H11B	0.9700
C5—C6	1.371 (2)	C14—H14	0.9300
C6—C7	1.413 (2)	C15—H15	0.9300
C6—C10	1.502 (2)	C16—H16	0.9300
C7—C8	1.359 (2)	C17—H17	0.9300
C8—C9	1.408 (2)	C19—H19	0.9300
C12—C13	1.452 (2)

Cl1···N2	3.4130 (12)	C15···H3^ix	2.9900
Cl1···C19	3.3776 (16)	C16···H3^ix	2.9200
Cl1···H11A	2.8000	C18···H8^vi	2.9100
Cl1···H19	3.0400	C19···H15^x	3.0800
Cl1···H16ⁱ	3.1300	C19···H19^iv	3.0300
Cl1···H11Bⁱⁱ	3.1400	C19···H8^vi	3.0300
O1···C2	3.0757 (18)	H3···O1	2.7300
O1···C3	3.0535 (18)	H3···H5	2.5100
O1···H3	2.7300	H3···H11B	2.3600
O1···H11B	2.5800	H3···C15^xi	2.9900
O1···H14	2.6400	H3···C16^xi	2.9200
O1···H7ⁱⁱⁱ	2.7400	H5···H3	2.5100
N2···Cl1	3.4130 (12)	H5···H10C	2.3400
N3···C19^iv	3.271 (2)	H5···C14^xi	2.7700
N1···H15^v	2.8000	H5···C15^xi	2.9600
N3···H19^iv	2.5100	H7···O1ⁱⁱⁱ	2.7400
N3···H8^vi	2.7300	H8···N3ⁱⁱ	2.7300
C1···C5^vii	3.573 (2)	H8···C18ⁱⁱ	2.9100
C2···O1	3.0757 (18)	H8···C19ⁱⁱ	3.0300
C3···O1	3.0535 (18)	H10A···C1ⁱⁱⁱ	2.9700
C3···C9^vii	3.592 (2)	H10A···C2ⁱⁱⁱ	2.8900
C3···C12	3.572 (2)	H10A···C3ⁱⁱⁱ	2.9100
C4···C4^vii	3.5715 (19)	H10A···C4ⁱⁱⁱ	3.0500
C4···C6ⁱⁱⁱ	3.547 (2)	H10A···C12ⁱⁱⁱ	3.0700
C5···C1^vii	3.572 (2)	H10B···H17^viii	2.4900
C6···C4ⁱⁱⁱ	3.547 (2)	H10B···H11A^vii	2.5100
C9···C3^vii	3.592 (2)	H10C···H5	2.3400
C12···C3	3.572 (2)	H11A···Cl1	2.8000
C16···C18ⁱ	3.587 (2)	H11A···H19	2.2400
C17···C18ⁱ	3.539 (2)	H11A···H10B^vii	2.5100
C17···C17ⁱ	3.557 (2)	H11B···O1	2.5800
C18···C17ⁱ	3.539 (2)	H11B···H3	2.3600
C18···C16ⁱ	3.587 (2)	H11B···Cl1^vi	3.1400
C19···N3^iv	3.271 (2)	H14···O1	2.6400
C19···Cl1	3.3776 (16)	H15···C19^xii	3.0800
C19···C19^iv	3.538 (2)	H15···N1^xiii	2.8000
C1···H10Aⁱⁱⁱ	2.9700	H16···Cl1ⁱ	3.1300
C2···H10Aⁱⁱⁱ	2.8900	H17···C10^xiv	2.9800
C3···H10Aⁱⁱⁱ	2.9100	H17···H10B^xiv	2.4900
C4···H10Aⁱⁱⁱ	3.0500	H19···Cl1	3.0400
C10···H17^viii	2.9800	H19···H11A	2.2400
C12···H10Aⁱⁱⁱ	3.0700	H19···N3^iv	2.5100
C14···H5^ix	2.7700	H19···C19^iv	3.0300
C15···H5^ix	2.9600

C1—N1—C9	117.14 (12)	C16—C17—C18	119.90 (17)
C11—N2—C12	118.32 (12)	N3—C18—C13	121.98 (13)
C11—N2—C19	120.35 (12)	N3—C18—C17	118.56 (14)
C12—N2—C19	121.18 (12)	C13—C18—C17	119.46 (14)
C18—N3—C19	116.34 (13)	N2—C19—N3	126.29 (14)
Cl1—C1—N1	115.34 (11)	C2—C3—H3	119.00
Cl1—C1—C2	117.89 (11)	C4—C3—H3	119.00
N1—C1—C2	126.78 (14)	C4—C5—H5	119.00
C1—C2—C3	115.35 (13)	C6—C5—H5	119.00
C1—C2—C11	123.66 (13)	C6—C7—H7	119.00
C3—C2—C11	120.99 (13)	C8—C7—H7	119.00
C2—C3—C4	121.45 (13)	C7—C8—H8	120.00
C3—C4—C5	123.08 (13)	C9—C8—H8	120.00
C3—C4—C9	117.63 (13)	C6—C10—H10A	110.00
C5—C4—C9	119.29 (13)	C6—C10—H10B	109.00
C4—C5—C6	121.62 (13)	C6—C10—H10C	109.00
C5—C6—C7	118.00 (14)	H10A—C10—H10B	109.00
C5—C6—C10	121.23 (14)	H10A—C10—H10C	109.00
C7—C6—C10	120.78 (14)	H10B—C10—H10C	109.00
C6—C7—C8	121.94 (14)	N2—C11—H11A	109.00
C7—C8—C9	120.39 (14)	N2—C11—H11B	109.00
N1—C9—C4	121.65 (13)	C2—C11—H11A	109.00
N1—C9—C8	119.58 (12)	C2—C11—H11B	109.00
C4—C9—C8	118.76 (13)	H11A—C11—H11B	108.00
N2—C11—C2	112.79 (12)	C13—C14—H14	120.00
O1—C12—N2	120.49 (14)	C15—C14—H14	120.00
O1—C12—C13	125.83 (14)	C14—C15—H15	120.00
N2—C12—C13	113.67 (12)	C16—C15—H15	120.00
C12—C13—C14	120.61 (14)	C15—C16—H16	120.00
C12—C13—C18	119.82 (13)	C17—C16—H16	120.00
C14—C13—C18	119.57 (14)	C16—C17—H17	120.00
C13—C14—C15	120.08 (16)	C18—C17—H17	120.00
C14—C15—C16	120.32 (17)	N2—C19—H19	117.00
C15—C16—C17	120.62 (19)	N3—C19—H19	117.00

C9—N1—C1—Cl1	−179.80 (10)	C3—C4—C9—N1	−0.4 (2)
C9—N1—C1—C2	0.3 (2)	C3—C4—C9—C8	178.79 (13)
C1—N1—C9—C4	0.4 (2)	C5—C4—C9—N1	−179.72 (13)
C1—N1—C9—C8	−178.82 (13)	C5—C4—C9—C8	−0.5 (2)
C12—N2—C11—C2	−69.62 (16)	C4—C5—C6—C7	0.0 (2)
C19—N2—C11—C2	114.68 (14)	C4—C5—C6—C10	179.76 (14)
C11—N2—C12—O1	−4.0 (2)	C5—C6—C7—C8	−0.5 (2)
C11—N2—C12—C13	174.94 (12)	C10—C6—C7—C8	179.74 (15)
C19—N2—C12—O1	171.64 (13)	C6—C7—C8—C9	0.5 (2)
C19—N2—C12—C13	−9.40 (18)	C7—C8—C9—N1	179.26 (14)
C11—N2—C19—N3	−179.97 (14)	C7—C8—C9—C4	0.1 (2)
C12—N2—C19—N3	4.5 (2)	O1—C12—C13—C14	7.1 (2)
C19—N3—C18—C13	−2.9 (2)	O1—C12—C13—C18	−172.61 (14)
C19—N3—C18—C17	176.95 (14)	N2—C12—C13—C14	−171.76 (13)
C18—N3—C19—N2	2.1 (2)	N2—C12—C13—C18	8.50 (19)
Cl1—C1—C2—C3	179.26 (11)	C12—C13—C14—C15	−179.62 (14)
Cl1—C1—C2—C11	−1.6 (2)	C18—C13—C14—C15	0.1 (2)
N1—C1—C2—C3	−0.8 (2)	C12—C13—C18—N3	−2.7 (2)
N1—C1—C2—C11	178.31 (14)	C12—C13—C18—C17	177.48 (13)
C1—C2—C3—C4	0.7 (2)	C14—C13—C18—N3	177.54 (13)
C11—C2—C3—C4	−178.43 (14)	C14—C13—C18—C17	−2.3 (2)
C1—C2—C11—N2	−75.60 (18)	C13—C14—C15—C16	1.7 (2)
C3—C2—C11—N2	103.49 (16)	C14—C15—C16—C17	−1.3 (3)
C2—C3—C4—C5	179.10 (14)	C15—C16—C17—C18	−0.9 (3)
C2—C3—C4—C9	−0.2 (2)	C16—C17—C18—N3	−177.16 (15)
C3—C4—C5—C6	−178.76 (14)	C16—C17—C18—C13	2.7 (2)
C9—C4—C5—C6	0.5 (2)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C1–C4/C9 and N2/N3/C12/C13/C18/C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N3^iv	0.93	2.51	3.271 (2)	139
C8—H8···Cg2ⁱⁱ	0.93	2.89	3.6598 (16)	142
C10—H10A···Cg1ⁱⁱⁱ	0.96	2.68	3.5189 (17)	146

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄ClN₃O
M_r	335.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.86728 (14), 14.7098 (3), 13.7055 (3)
β (°)	102.1500 (17)
V (Å³)	1550.56 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.25 × 0.21 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur E CCD diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.938, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	15755, 3048, 2417
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.14
No. of reflections	3048
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C1–C4/C9 and N2/N3/C12/C13/C18/C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N3ⁱ	0.93	2.51	3.271 (2)	139
C8—H8···Cg2ⁱⁱ	0.93	2.89	3.6598 (16)	142
C10—H10A···Cg1ⁱⁱⁱ	0.96	2.68	3.5189 (17)	146

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+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 also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

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