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

In the title compound, C(23)H(15)ClN(2)O, 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 inter-actions 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 = 370.82

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.138

S = 1.00

5019 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H15ClN2O	Z = 2
Mr = 370.82	F(000) = 384
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0812P)2 + 0.1735P] where P = (Fo2 + 2Fc2)/3
5019 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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.