12-(4-Meth-oxy-benzo-yl)-2-methyl-benzo[f]pyrido[1,2-a]indole-6,11-dione.

In the title compound, C(25)H(17)NO(4), the indolizine fused naphthaquinone unit is approximately planar [r.m.s deviation = 0.0678 Å] and makes a dihedral angle of 57.82 (5)° with the benzene ring of the meth-oxy-benzene group. The naphtho-quinone O atoms deviate, in the same sense, from the mean plane of the fused six-membered rings by 0.2001 (14) and 0.0516 (14) Å. In the crystal there is π-π stacking of inversion-related pairs of mol-ecules [inter-planar spacing = 3.514 (2) Å].

Related literature

For general background to the applications and biological activity of indolizine derivatives, see: Švorc et al. (2009 ▶). For the synthesis of indolizines, see: Babaev et al. (2005 ▶), and for their use as inter­mediates in the synthesis of indolizidines, see: Kloubert et al. (2012 ▶). For the crystal structures of similar compounds, see: Liu et al. (2011 ▶); Ramesh et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H17NO4

M = 395.40

Monoclinic,

a = 8.1346 (3) Å

b = 23.2926 (8) Å

c = 10.1505 (3) Å

β = 97.304 (2)°

V = 1907.67 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.972, T max = 0.982

18096 measured reflections

3852 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.04

3852 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040408/pk2443sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040408/pk2443Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040408/pk2443Isup3.cml

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

C25H17NO4	F(000) = 824
Mr = 395.40	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5015 reflections
a = 8.1346 (3) Å	θ = 2.2–26.3°
b = 23.2926 (8) Å	µ = 0.09 mm−1
c = 10.1505 (3) Å	T = 293 K
β = 97.304 (2)°	Block, brown
V = 1907.67 (11) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3852 independent reflections
Radiation source: fine-focus sealed tube	2856 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scan	θmax = 26.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.972, Tmax = 0.982	k = −28→29
18096 measured reflections	l = −12→10

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.4967P] where P = (Fo2 + 2Fc2)/3
3852 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.20 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	0.17994 (16)	0.53308 (6)	0.57068 (13)	0.0388 (3)
O2	0.34773 (17)	0.42161 (6)	0.56349 (14)	0.0628 (4)
C8	0.24197 (19)	0.50723 (7)	0.46488 (15)	0.0376 (4)
C9	0.21764 (19)	0.54500 (7)	0.35825 (16)	0.0383 (4)
O1	0.2104 (2)	0.55356 (6)	0.12630 (12)	0.0652 (4)
C6	0.3785 (2)	0.43608 (7)	0.33619 (18)	0.0435 (4)
C18	0.0992 (2)	0.64903 (7)	0.32447 (17)	0.0439 (4)
C19	0.2224 (2)	0.67504 (7)	0.24748 (16)	0.0379 (4)
C1	0.3460 (2)	0.47115 (7)	0.22307 (18)	0.0443 (4)
C21	0.5041 (2)	0.68874 (7)	0.20229 (17)	0.0431 (4)
H21	0.6165	0.6806	0.2219	0.052*
O3	−0.03169 (17)	0.67344 (7)	0.33481 (16)	0.0714 (5)
C16	0.1778 (2)	0.51365 (9)	0.69868 (16)	0.0477 (4)
H16	0.2195	0.4776	0.7238	0.057*
C10	0.2554 (2)	0.52654 (7)	0.22716 (17)	0.0444 (4)
C12	0.11594 (19)	0.58666 (7)	0.53067 (16)	0.0399 (4)
C7	0.3231 (2)	0.45262 (8)	0.46517 (17)	0.0426 (4)
C14	0.0491 (2)	0.60280 (9)	0.75177 (18)	0.0509 (5)
C23	0.2821 (2)	0.74026 (8)	0.0772 (2)	0.0539 (5)
H23	0.2453	0.7662	0.0101	0.065*
O4	0.54786 (16)	0.75454 (6)	0.02430 (14)	0.0634 (4)
C20	0.3900 (2)	0.66254 (7)	0.27206 (16)	0.0409 (4)
H20	0.4265	0.6358	0.3373	0.049*
C13	0.0496 (2)	0.62101 (8)	0.62437 (18)	0.0464 (4)
H13	0.0052	0.6567	0.5991	0.056*
C22	0.4494 (2)	0.72723 (7)	0.10299 (17)	0.0443 (4)
C2	0.3967 (2)	0.45322 (9)	0.1042 (2)	0.0553 (5)
H2	0.3732	0.4758	0.0285	0.066*
C11	0.14110 (19)	0.59490 (7)	0.39734 (16)	0.0403 (4)
C24	0.1712 (2)	0.71529 (8)	0.14967 (18)	0.0483 (4)
H24	0.0598	0.7253	0.1334	0.058*
C15	0.1142 (2)	0.54769 (9)	0.78676 (18)	0.0539 (5)
H15	0.1129	0.5346	0.8732	0.065*
C4	0.5135 (3)	0.36798 (9)	0.2080 (2)	0.0644 (6)
H4	0.5702	0.3335	0.2030	0.077*
C5	0.4614 (2)	0.38467 (8)	0.3266 (2)	0.0538 (5)
H5	0.4824	0.3611	0.4008	0.065*
C17	−0.0160 (3)	0.63983 (11)	0.8546 (2)	0.0731 (7)
H17A	−0.0058	0.6197	0.9379	0.110*
H17B	−0.1305	0.6486	0.8270	0.110*
H17C	0.0467	0.6748	0.8649	0.110*
C3	0.4816 (3)	0.40227 (9)	0.0974 (2)	0.0646 (6)
H3	0.5174	0.3911	0.0178	0.077*
C25	0.7210 (2)	0.74482 (11)	0.0475 (3)	0.0754 (7)
H25A	0.7748	0.7666	−0.0149	0.113*
H25B	0.7430	0.7047	0.0368	0.113*
H25C	0.7624	0.7565	0.1362	0.113*

	U11	U22	U33	U12	U13	U23
N	0.0378 (7)	0.0458 (8)	0.0328 (7)	−0.0053 (6)	0.0042 (6)	0.0017 (6)
O2	0.0696 (9)	0.0613 (9)	0.0577 (8)	0.0171 (7)	0.0086 (7)	0.0195 (7)
C8	0.0367 (8)	0.0409 (9)	0.0352 (9)	−0.0036 (7)	0.0045 (7)	0.0012 (7)
C9	0.0375 (8)	0.0406 (9)	0.0370 (9)	−0.0022 (7)	0.0061 (7)	0.0005 (7)
O1	0.1040 (11)	0.0559 (8)	0.0363 (7)	0.0112 (8)	0.0117 (7)	0.0047 (6)
C6	0.0366 (9)	0.0411 (10)	0.0529 (11)	−0.0042 (7)	0.0058 (8)	−0.0034 (8)
C18	0.0452 (10)	0.0427 (10)	0.0444 (10)	0.0067 (8)	0.0081 (8)	0.0021 (8)
C19	0.0417 (9)	0.0344 (9)	0.0377 (9)	0.0031 (7)	0.0049 (7)	−0.0014 (7)
C1	0.0436 (9)	0.0431 (10)	0.0479 (10)	−0.0067 (7)	0.0123 (8)	−0.0052 (8)
C21	0.0389 (9)	0.0444 (10)	0.0453 (10)	0.0049 (7)	0.0033 (7)	−0.0012 (8)
O3	0.0561 (8)	0.0741 (10)	0.0893 (11)	0.0229 (7)	0.0302 (8)	0.0266 (8)
C16	0.0476 (10)	0.0604 (12)	0.0346 (9)	−0.0068 (9)	0.0031 (8)	0.0086 (9)
C10	0.0543 (10)	0.0411 (10)	0.0388 (10)	−0.0048 (8)	0.0097 (8)	0.0002 (8)
C12	0.0353 (8)	0.0445 (9)	0.0402 (9)	−0.0055 (7)	0.0056 (7)	−0.0012 (8)
C7	0.0374 (9)	0.0446 (10)	0.0447 (10)	−0.0034 (7)	0.0014 (7)	0.0053 (8)
C14	0.0436 (10)	0.0670 (13)	0.0433 (10)	−0.0125 (9)	0.0095 (8)	−0.0108 (9)
C23	0.0517 (11)	0.0515 (11)	0.0579 (12)	0.0064 (9)	0.0044 (9)	0.0211 (9)
O4	0.0549 (8)	0.0670 (9)	0.0710 (9)	−0.0051 (7)	0.0179 (7)	0.0200 (7)
C20	0.0460 (9)	0.0394 (9)	0.0365 (9)	0.0073 (7)	0.0017 (7)	0.0036 (7)
C13	0.0422 (9)	0.0507 (10)	0.0473 (10)	−0.0040 (8)	0.0102 (8)	−0.0081 (8)
C22	0.0485 (10)	0.0394 (9)	0.0462 (10)	−0.0028 (8)	0.0108 (8)	−0.0006 (8)
C2	0.0608 (12)	0.0542 (11)	0.0543 (11)	−0.0064 (9)	0.0202 (9)	−0.0091 (9)
C11	0.0399 (9)	0.0423 (9)	0.0395 (9)	−0.0012 (7)	0.0079 (7)	0.0011 (7)
C24	0.0383 (9)	0.0473 (10)	0.0582 (11)	0.0071 (8)	0.0024 (8)	0.0112 (9)
C15	0.0534 (11)	0.0751 (14)	0.0335 (9)	−0.0127 (10)	0.0073 (8)	−0.0006 (9)
C4	0.0555 (12)	0.0530 (12)	0.0865 (16)	0.0040 (10)	0.0153 (11)	−0.0176 (12)
C5	0.0478 (10)	0.0449 (10)	0.0682 (13)	0.0010 (8)	0.0054 (9)	−0.0037 (9)
C17	0.0779 (15)	0.0912 (17)	0.0537 (12)	−0.0094 (13)	0.0219 (11)	−0.0256 (12)
C3	0.0655 (13)	0.0615 (13)	0.0712 (14)	−0.0054 (11)	0.0266 (11)	−0.0222 (12)
C25	0.0506 (12)	0.0877 (17)	0.0921 (17)	−0.0101 (11)	0.0251 (12)	0.0067 (14)

N—C16	1.378 (2)	C14—C13	1.361 (3)
N—C8	1.381 (2)	C14—C15	1.416 (3)
N—C12	1.393 (2)	C14—C17	1.502 (3)
O2—C7	1.228 (2)	C23—C24	1.365 (2)
C8—C9	1.389 (2)	C23—C22	1.386 (3)
C8—C7	1.433 (2)	C23—H23	0.9300
C9—C11	1.400 (2)	O4—C22	1.359 (2)
C9—C10	1.467 (2)	O4—C25	1.416 (2)
O1—C10	1.218 (2)	C20—H20	0.9300
C6—C5	1.384 (2)	C13—H13	0.9300
C6—C1	1.407 (2)	C2—C3	1.379 (3)
C6—C7	1.489 (2)	C2—H2	0.9300
C18—O3	1.223 (2)	C24—H24	0.9300
C18—C19	1.477 (2)	C15—H15	0.9300
C18—C11	1.479 (2)	C4—C3	1.375 (3)
C19—C20	1.385 (2)	C4—C5	1.382 (3)
C19—C24	1.390 (2)	C4—H4	0.9300
C1—C2	1.388 (2)	C5—H5	0.9300
C1—C10	1.489 (2)	C17—H17A	0.9600
C21—C20	1.379 (2)	C17—H17B	0.9600
C21—C22	1.380 (2)	C17—H17C	0.9600
C21—H21	0.9300	C3—H3	0.9300
C16—C15	1.347 (3)	C25—H25A	0.9600
C16—H16	0.9300	C25—H25B	0.9600
C12—C13	1.402 (2)	C25—H25C	0.9600
C12—C11	1.407 (2)
C16—N—C8	129.76 (15)	C21—C20—C19	121.72 (15)
C16—N—C12	121.34 (15)	C21—C20—H20	119.1
C8—N—C12	108.89 (13)	C19—C20—H20	119.1
N—C8—C9	107.44 (14)	C14—C13—C12	120.95 (18)
N—C8—C7	126.80 (14)	C14—C13—H13	119.5
C9—C8—C7	125.71 (15)	C12—C13—H13	119.5
C8—C9—C11	109.24 (14)	O4—C22—C21	125.05 (16)
C8—C9—C10	119.70 (15)	O4—C22—C23	115.09 (16)
C11—C9—C10	130.71 (15)	C21—C22—C23	119.86 (16)
C5—C6—C1	119.22 (17)	C3—C2—C1	120.6 (2)
C5—C6—C7	119.38 (17)	C3—C2—H2	119.7
C1—C6—C7	121.39 (15)	C1—C2—H2	119.7
O3—C18—C19	120.77 (16)	C9—C11—C12	106.48 (14)
O3—C18—C11	120.06 (16)	C9—C11—C18	130.43 (15)
C19—C18—C11	119.03 (14)	C12—C11—C18	122.99 (15)
C20—C19—C24	117.97 (15)	C23—C24—C19	120.92 (16)
C20—C19—C18	122.49 (15)	C23—C24—H24	119.5
C24—C19—C18	119.50 (15)	C19—C24—H24	119.5
C2—C1—C6	119.25 (17)	C16—C15—C14	122.00 (17)
C2—C1—C10	119.19 (17)	C16—C15—H15	119.0
C6—C1—C10	121.54 (15)	C14—C15—H15	119.0
C20—C21—C22	119.14 (16)	C3—C4—C5	120.08 (19)
C20—C21—H21	120.4	C3—C4—H4	120.0
C22—C21—H21	120.4	C5—C4—H4	120.0
C15—C16—N	119.00 (18)	C4—C5—C6	120.7 (2)
C15—C16—H16	120.5	C4—C5—H5	119.6
N—C16—H16	120.5	C6—C5—H5	119.6
O1—C10—C9	122.39 (16)	C14—C17—H17A	109.5
O1—C10—C1	121.42 (16)	C14—C17—H17B	109.5
C9—C10—C1	116.13 (15)	H17A—C17—H17B	109.5
N—C12—C13	118.38 (15)	C14—C17—H17C	109.5
N—C12—C11	107.93 (14)	H17A—C17—H17C	109.5
C13—C12—C11	133.63 (17)	H17B—C17—H17C	109.5
O2—C7—C8	123.46 (17)	C4—C3—C2	120.1 (2)
O2—C7—C6	121.77 (16)	C4—C3—H3	119.9
C8—C7—C6	114.76 (15)	C2—C3—H3	119.9
C13—C14—C15	118.33 (17)	O4—C25—H25A	109.5
C13—C14—C17	121.7 (2)	O4—C25—H25B	109.5
C15—C14—C17	119.98 (18)	H25A—C25—H25B	109.5
C24—C23—C22	120.34 (17)	O4—C25—H25C	109.5
C24—C23—H23	119.8	H25A—C25—H25C	109.5
C22—C23—H23	119.8	H25B—C25—H25C	109.5
C22—O4—C25	118.39 (16)
C16—N—C8—C9	−178.53 (15)	C22—C21—C20—C19	−1.8 (3)
C12—N—C8—C9	0.38 (17)	C24—C19—C20—C21	−0.2 (3)
C16—N—C8—C7	−1.0 (3)	C18—C19—C20—C21	−177.69 (16)
C12—N—C8—C7	177.96 (15)	C15—C14—C13—C12	−1.4 (3)
N—C8—C9—C11	0.40 (18)	C17—C14—C13—C12	177.84 (17)
C7—C8—C9—C11	−177.21 (15)	N—C12—C13—C14	0.7 (2)
N—C8—C9—C10	−173.46 (14)	C11—C12—C13—C14	−176.11 (17)
C7—C8—C9—C10	8.9 (2)	C25—O4—C22—C21	−2.3 (3)
O3—C18—C19—C20	154.62 (18)	C25—O4—C22—C23	178.04 (18)
C11—C18—C19—C20	−21.0 (2)	C20—C21—C22—O4	−177.84 (17)
O3—C18—C19—C24	−22.9 (3)	C20—C21—C22—C23	1.8 (3)
C11—C18—C19—C24	161.52 (16)	C24—C23—C22—O4	179.80 (17)
C5—C6—C1—C2	0.4 (3)	C24—C23—C22—C21	0.1 (3)
C7—C6—C1—C2	−178.47 (16)	C6—C1—C2—C3	−1.5 (3)
C5—C6—C1—C10	179.22 (16)	C10—C1—C2—C3	179.66 (17)
C7—C6—C1—C10	0.3 (2)	C8—C9—C11—C12	−1.00 (18)
C8—N—C16—C15	177.94 (16)	C10—C9—C11—C12	171.95 (17)
C12—N—C16—C15	−0.9 (2)	C8—C9—C11—C18	175.43 (16)
C8—C9—C10—O1	167.00 (17)	C10—C9—C11—C18	−11.6 (3)
C11—C9—C10—O1	−5.3 (3)	N—C12—C11—C9	1.22 (18)
C8—C9—C10—C1	−10.4 (2)	C13—C12—C11—C9	178.26 (17)
C11—C9—C10—C1	177.31 (16)	N—C12—C11—C18	−175.55 (14)
C2—C1—C10—O1	7.4 (3)	C13—C12—C11—C18	1.5 (3)
C6—C1—C10—O1	−171.35 (17)	O3—C18—C11—C9	140.6 (2)
C2—C1—C10—C9	−175.19 (16)	C19—C18—C11—C9	−43.8 (3)
C6—C1—C10—C9	6.0 (2)	O3—C18—C11—C12	−43.5 (3)
C16—N—C12—C13	0.5 (2)	C19—C18—C11—C12	132.13 (17)
C8—N—C12—C13	−178.57 (14)	C22—C23—C24—C19	−2.1 (3)
C16—N—C12—C11	178.02 (14)	C20—C19—C24—C23	2.1 (3)
C8—N—C12—C11	−1.00 (17)	C18—C19—C24—C23	179.74 (17)
N—C8—C7—O2	−0.2 (3)	N—C16—C15—C14	0.2 (3)
C9—C8—C7—O2	176.99 (17)	C13—C14—C15—C16	1.0 (3)
N—C8—C7—C6	−179.40 (14)	C17—C14—C15—C16	−178.26 (18)
C9—C8—C7—C6	−2.2 (2)	C3—C4—C5—C6	−0.7 (3)
C5—C6—C7—O2	−0.6 (3)	C1—C6—C5—C4	0.7 (3)
C1—C6—C7—O2	178.29 (16)	C7—C6—C5—C4	179.60 (16)
C5—C6—C7—C8	178.63 (15)	C5—C4—C3—C2	−0.4 (3)
C1—C6—C7—C8	−2.5 (2)	C1—C2—C3—C4	1.5 (3)