12-Benzoyl-2-methyl-naphtho-[2,3-b]indolizine-6,11-dione.

In the title compound, C(24)H(15)NO(3), the fused naphthaquin-one-pyrrole unit is approximately planar, the naphthaquinone ring system making a dihedral angle of 2.91 (10)° with the pyrrole ring. The plane of the pyrrole ring makes a dihedral angle 61.64 (14)° with that of the benzene ring of the benzoyl-methyl-ene group. The crystal structure is stablized by intra-molecular C-H⋯O inter-actions.

Related literature

For the properties of indolizine, see Olden et al. (1991 ▶); Jaffrezou et al. (1992 ▶). For the preparation of benzo[f]pyrido[1,2-a]indole-6,11-dione, see Pratt et al. (1957 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H15NO3

M = 365.37

Monoclinic,

a = 7.1260 (14) Å

b = 10.125 (2) Å

c = 24.352 (5) Å

β = 90.22 (3)°

V = 1757.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ▶) T min = 0.973, T max = 0.991

3371 measured reflections

3103 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.062

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.169

S = 1.02

3103 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019623/ds2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019623/ds2112Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019623/ds2112Isup3.cml

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

C24H15NO3	F(000) = 760
Mr = 365.37	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Melting point: 538 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1260 (14) Å	Cell parameters from 25 reflections
b = 10.125 (2) Å	θ = 9–12°
c = 24.352 (5) Å	µ = 0.09 mm−1
β = 90.22 (3)°	T = 295 K
V = 1757.0 (6) Å3	Block, red
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
graphite	θmax = 25.0°, θmin = 1.7°
ω/2θ scans	h = −8→0
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = −12→0
Tmin = 0.973, Tmax = 0.991	l = −28→28
3371 measured reflections	3 standard reflections every 200 reflections
3103 independent reflections	intensity decay: none

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.0651P] where P = (Fo2 + 2Fc2)/3
3103 reflections	(Δ/σ)max = 0.006
254 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N	0.1808 (3)	0.6115 (3)	0.44928 (11)	0.0478 (7)
C24	0.2311 (4)	0.4972 (3)	0.47630 (13)	0.0446 (8)
O3	0.2792 (4)	0.5789 (3)	0.56513 (10)	0.0699 (8)
O2	0.2339 (4)	0.1643 (3)	0.42739 (10)	0.0806 (9)
C23	0.3188 (4)	0.2429 (3)	0.51506 (14)	0.0492 (9)
C22	0.3265 (4)	0.3501 (3)	0.55128 (14)	0.0494 (9)
C21	0.2309 (4)	0.3959 (3)	0.43837 (13)	0.0470 (8)
C20	0.1497 (4)	0.5816 (3)	0.39425 (14)	0.0490 (9)
C19	0.3601 (5)	0.1177 (4)	0.53431 (16)	0.0630 (10)
H19	0.3511	0.0459	0.5107	0.076*
C18	0.2598 (5)	0.2599 (4)	0.45665 (15)	0.0571 (10)
C17	0.2775 (5)	0.4848 (4)	0.53324 (14)	0.0508 (9)
C16	0.1643 (5)	0.7379 (4)	0.46870 (15)	0.0553 (9)
H16	0.1848	0.7557	0.5057	0.066*
C15	0.1807 (5)	0.4458 (4)	0.38678 (13)	0.0525 (9)
C14	0.3024 (6)	0.2844 (3)	0.31344 (13)	0.0572 (10)
O1	0.0328 (4)	0.4141 (3)	0.30306 (11)	0.0967 (10)
C13	0.1000 (5)	0.6856 (4)	0.35921 (15)	0.0594 (10)
H13	0.0775	0.6684	0.3223	0.071*
C12	0.1184 (5)	0.8354 (4)	0.43411 (17)	0.0633 (11)
H12	0.1092	0.9213	0.4475	0.076*
C11	0.3777 (5)	0.3285 (4)	0.60562 (14)	0.0621 (10)
H11	0.3820	0.3988	0.6302	0.075*
C10	0.4852 (6)	0.2881 (4)	0.33161 (15)	0.0648 (11)
H10	0.5208	0.3493	0.3582	0.078*
C9	0.0840 (5)	0.8116 (4)	0.37831 (17)	0.0617 (10)
C8	0.1615 (5)	0.3819 (4)	0.33307 (15)	0.0611 (10)
C7	0.4220 (5)	0.2029 (5)	0.62324 (17)	0.0725 (12)
H7	0.4577	0.1894	0.6596	0.087*
C6	0.2519 (7)	0.1918 (4)	0.27499 (15)	0.0780 (13)
H6	0.1291	0.1897	0.2619	0.094*
C5	0.3799 (9)	0.1024 (5)	0.25553 (18)	0.0969 (17)
H5	0.3424	0.0377	0.2307	0.116*
C4	0.4142 (5)	0.0979 (4)	0.58804 (17)	0.0733 (12)
H4	0.4453	0.0137	0.6003	0.088*
C3	0.6168 (7)	0.2010 (4)	0.31047 (18)	0.0839 (13)
H3	0.7413	0.2054	0.3219	0.101*
C2	0.5615 (9)	0.1081 (5)	0.2725 (2)	0.0987 (17)
H2	0.6488	0.0491	0.2583	0.118*
C1	0.0376 (6)	0.9245 (4)	0.34044 (18)	0.0885 (14)
H1A	0.0216	0.8917	0.3037	0.133*
H1B	0.1379	0.9877	0.3412	0.133*
H1C	−0.0765	0.9660	0.3523	0.133*

	U11	U22	U33	U12	U13	U23
N	0.0436 (17)	0.0484 (18)	0.0514 (18)	−0.0055 (14)	0.0046 (13)	−0.0026 (15)
C24	0.0354 (18)	0.048 (2)	0.050 (2)	0.0007 (16)	0.0012 (16)	−0.0009 (18)
O3	0.083 (2)	0.0695 (18)	0.0574 (16)	−0.0013 (15)	−0.0041 (13)	−0.0141 (14)
O2	0.123 (3)	0.0532 (17)	0.0652 (17)	−0.0080 (16)	−0.0049 (16)	−0.0040 (14)
C23	0.0345 (19)	0.055 (2)	0.058 (2)	0.0068 (17)	0.0040 (15)	0.0040 (19)
C22	0.037 (2)	0.059 (2)	0.051 (2)	0.0021 (17)	0.0061 (16)	0.0020 (19)
C21	0.040 (2)	0.049 (2)	0.052 (2)	−0.0050 (17)	0.0013 (16)	−0.0032 (18)
C20	0.039 (2)	0.058 (2)	0.050 (2)	−0.0035 (17)	0.0000 (16)	0.0002 (19)
C19	0.056 (2)	0.061 (3)	0.072 (3)	0.010 (2)	0.004 (2)	0.003 (2)
C18	0.058 (2)	0.058 (2)	0.055 (2)	−0.008 (2)	0.0059 (18)	−0.003 (2)
C17	0.041 (2)	0.056 (2)	0.055 (2)	−0.0032 (17)	0.0051 (17)	−0.005 (2)
C16	0.050 (2)	0.055 (2)	0.060 (2)	−0.0076 (18)	0.0073 (18)	−0.007 (2)
C15	0.052 (2)	0.059 (2)	0.046 (2)	−0.0061 (18)	−0.0012 (16)	−0.0006 (19)
C14	0.079 (3)	0.053 (2)	0.040 (2)	−0.011 (2)	0.0035 (19)	0.0030 (18)
O1	0.099 (2)	0.114 (3)	0.077 (2)	0.009 (2)	−0.0381 (18)	−0.0112 (18)
C13	0.054 (2)	0.067 (3)	0.057 (2)	−0.001 (2)	−0.0025 (18)	0.009 (2)
C12	0.062 (3)	0.050 (2)	0.077 (3)	−0.011 (2)	0.004 (2)	0.004 (2)
C11	0.054 (2)	0.081 (3)	0.051 (2)	−0.002 (2)	0.0008 (18)	0.006 (2)
C10	0.082 (3)	0.055 (2)	0.057 (2)	−0.001 (2)	0.004 (2)	−0.001 (2)
C9	0.050 (2)	0.059 (3)	0.076 (3)	−0.002 (2)	0.0022 (19)	0.011 (2)
C8	0.068 (3)	0.065 (3)	0.049 (2)	−0.011 (2)	−0.012 (2)	0.003 (2)
C7	0.058 (3)	0.098 (3)	0.062 (3)	0.007 (2)	0.002 (2)	0.020 (3)
C6	0.119 (4)	0.069 (3)	0.046 (2)	−0.012 (3)	−0.001 (2)	−0.004 (2)
C5	0.166 (6)	0.070 (3)	0.056 (3)	−0.010 (4)	0.017 (3)	−0.015 (2)
C4	0.072 (3)	0.076 (3)	0.072 (3)	0.018 (2)	0.008 (2)	0.020 (3)
C3	0.089 (3)	0.079 (3)	0.084 (3)	0.012 (3)	0.025 (3)	0.009 (3)
C2	0.143 (5)	0.075 (3)	0.079 (4)	0.014 (4)	0.046 (3)	−0.002 (3)
C1	0.091 (3)	0.072 (3)	0.102 (3)	0.000 (3)	−0.003 (3)	0.030 (3)

N—C16	1.369 (4)	O1—C8	1.215 (4)
N—C24	1.379 (4)	C13—C9	1.363 (5)
N—C20	1.391 (4)	C13—H13	0.9300
C24—C21	1.380 (4)	C12—C9	1.401 (5)
C24—C17	1.430 (5)	C12—H12	0.9300
O3—C17	1.230 (4)	C11—C7	1.378 (5)
O2—C18	1.215 (4)	C11—H11	0.9300
C23—C19	1.382 (5)	C10—C3	1.388 (5)
C23—C22	1.400 (4)	C10—H10	0.9300
C23—C18	1.492 (5)	C9—C1	1.505 (5)
C22—C11	1.389 (5)	C7—C4	1.366 (5)
C22—C17	1.474 (5)	C7—H7	0.9300
C21—C15	1.399 (4)	C6—C5	1.372 (6)
C21—C18	1.462 (5)	C6—H6	0.9300
C20—C13	1.400 (4)	C5—C2	1.358 (6)
C20—C15	1.404 (5)	C5—H5	0.9300
C19—C4	1.377 (5)	C4—H4	0.9300
C19—H19	0.9300	C3—C2	1.376 (6)
C16—C12	1.338 (5)	C3—H3	0.9300
C16—H16	0.9300	C2—H2	0.9300
C15—C8	1.465 (5)	C1—H1A	0.9600
C14—C6	1.372 (5)	C1—H1B	0.9600
C14—C10	1.375 (5)	C1—H1C	0.9600
C14—C8	1.488 (5)
C16—N—C24	130.0 (3)	C16—C12—C9	121.7 (4)
C16—N—C20	121.5 (3)	C16—C12—H12	119.2
C24—N—C20	108.5 (3)	C9—C12—H12	119.2
N—C24—C21	107.7 (3)	C7—C11—C22	120.1 (4)
N—C24—C17	126.5 (3)	C7—C11—H11	120.0
C21—C24—C17	125.7 (3)	C22—C11—H11	120.0
C19—C23—C22	119.3 (3)	C14—C10—C3	120.3 (4)
C19—C23—C18	119.2 (3)	C14—C10—H10	119.9
C22—C23—C18	121.4 (3)	C3—C10—H10	119.9
C11—C22—C23	119.2 (3)	C13—C9—C12	118.5 (4)
C11—C22—C17	119.4 (3)	C13—C9—C1	121.3 (4)
C23—C22—C17	121.4 (3)	C12—C9—C1	120.1 (4)
C24—C21—C15	109.4 (3)	O1—C8—C15	119.1 (4)
C24—C21—C18	119.8 (3)	O1—C8—C14	119.6 (3)
C15—C21—C18	130.5 (3)	C15—C8—C14	121.3 (3)
N—C20—C13	117.6 (3)	C4—C7—C11	120.9 (4)
N—C20—C15	108.3 (3)	C4—C7—H7	119.6
C13—C20—C15	134.2 (3)	C11—C7—H7	119.5
C23—C19—C4	120.9 (4)	C14—C6—C5	120.9 (5)
C23—C19—H19	119.5	C14—C6—H6	119.5
C4—C19—H19	119.5	C5—C6—H6	119.5
O2—C18—C21	123.4 (3)	C2—C5—C6	120.1 (5)
O2—C18—C23	120.6 (3)	C2—C5—H5	120.0
C21—C18—C23	116.0 (3)	C6—C5—H5	120.0
O3—C17—C24	123.1 (3)	C7—C4—C19	119.6 (4)
O3—C17—C22	121.8 (3)	C7—C4—H4	120.2
C24—C17—C22	115.1 (3)	C19—C4—H4	120.2
C12—C16—N	119.6 (3)	C2—C3—C10	119.5 (5)
C12—C16—H16	120.2	C2—C3—H3	120.3
N—C16—H16	120.2	C10—C3—H3	120.3
C21—C15—C20	106.1 (3)	C5—C2—C3	120.2 (5)
C21—C15—C8	131.6 (3)	C5—C2—H2	119.9
C20—C15—C8	122.3 (3)	C3—C2—H2	119.9
C6—C14—C10	119.0 (4)	C9—C1—H1A	109.5
C6—C14—C8	119.8 (4)	C9—C1—H1B	109.5
C10—C14—C8	121.2 (3)	H1A—C1—H1B	109.5
C9—C13—C20	121.1 (4)	C9—C1—H1C	109.5
C9—C13—H13	119.4	H1A—C1—H1C	109.5
C20—C13—H13	119.4	H1B—C1—H1C	109.5
C16—N—C24—C21	−178.7 (3)	C24—C21—C15—C20	−0.1 (4)
C20—N—C24—C21	−0.2 (3)	C18—C21—C15—C20	172.7 (3)
C16—N—C24—C17	0.7 (5)	C24—C21—C15—C8	179.2 (3)
C20—N—C24—C17	179.2 (3)	C18—C21—C15—C8	−8.0 (6)
C19—C23—C22—C11	0.7 (5)	N—C20—C15—C21	0.0 (4)
C18—C23—C22—C11	178.3 (3)	C13—C20—C15—C21	178.8 (4)
C19—C23—C22—C17	−177.9 (3)	N—C20—C15—C8	−179.4 (3)
C18—C23—C22—C17	−0.2 (5)	C13—C20—C15—C8	−0.6 (6)
N—C24—C21—C15	0.2 (4)	N—C20—C13—C9	0.4 (5)
C17—C24—C21—C15	−179.2 (3)	C15—C20—C13—C9	−178.3 (4)
N—C24—C21—C18	−173.5 (3)	N—C16—C12—C9	0.9 (5)
C17—C24—C21—C18	7.1 (5)	C23—C22—C11—C7	0.7 (5)
C16—N—C20—C13	−0.2 (4)	C17—C22—C11—C7	179.3 (3)
C24—N—C20—C13	−178.9 (3)	C6—C14—C10—C3	1.2 (5)
C16—N—C20—C15	178.8 (3)	C8—C14—C10—C3	−176.3 (3)
C24—N—C20—C15	0.1 (3)	C20—C13—C9—C12	0.0 (5)
C22—C23—C19—C4	−2.1 (5)	C20—C13—C9—C1	177.8 (3)
C18—C23—C19—C4	−179.7 (3)	C16—C12—C9—C13	−0.7 (5)
C24—C21—C18—O2	168.7 (3)	C16—C12—C9—C1	−178.5 (4)
C15—C21—C18—O2	−3.5 (6)	C21—C15—C8—O1	140.5 (4)
C24—C21—C18—C23	−9.5 (5)	C20—C15—C8—O1	−40.3 (5)
C15—C21—C18—C23	178.3 (3)	C21—C15—C8—C14	−43.1 (6)
C19—C23—C18—O2	5.7 (5)	C20—C15—C8—C14	136.1 (4)
C22—C23—C18—O2	−171.9 (3)	C6—C14—C8—O1	−27.8 (5)
C19—C23—C18—C21	−176.0 (3)	C10—C14—C8—O1	149.7 (4)
C22—C23—C18—C21	6.4 (4)	C6—C14—C8—C15	155.8 (3)
N—C24—C17—O3	−0.8 (5)	C10—C14—C8—C15	−26.7 (5)
C21—C24—C17—O3	178.5 (3)	C22—C11—C7—C4	−0.8 (6)
N—C24—C17—C22	−179.9 (3)	C10—C14—C6—C5	1.3 (5)
C21—C24—C17—C22	−0.7 (5)	C8—C14—C6—C5	178.8 (4)
C11—C22—C17—O3	−0.5 (5)	C14—C6—C5—C2	−2.9 (7)
C23—C22—C17—O3	178.1 (3)	C11—C7—C4—C19	−0.5 (6)
C11—C22—C17—C24	178.6 (3)	C23—C19—C4—C7	1.9 (6)
C23—C22—C17—C24	−2.8 (4)	C14—C10—C3—C2	−2.1 (6)
C24—N—C16—C12	177.9 (3)	C6—C5—C2—C3	2.0 (7)
C20—N—C16—C12	−0.5 (5)	C10—C3—C2—C5	0.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3i	0.93	2.45	3.305 (5)	152
C16—H16···O3	0.93	2.40	2.960 (5)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3i	0.93	2.45	3.305 (5)	152

Symmetry code: (i) .