Ethyl 9-fluoro-5,12-dioxo-5,12-dihydro-indolizino[2,3-g]quinoline-6-carboxyl-ate.

In the title mol-ecule, C(18)H(11)FN(2)O(4), the fused four- ring system is essentially planar, with an r.m.s. deviation of 0.032 Å. In the crystal, mol-ecules are connected by π-π stacking inter-actions [centroid-centroid distances = 3.5684 (9) and 3.8247 (9) Å] into chains along [100].

Related literature

The title compound was obtained in an attempt to synthesize a Top1 (DNA topoisomerase IB) inhibitor. For general background to Top1, see: Pommier (2006 ▶). For the synthesis, see: Shen et al. (2008 ▶); Cheng et al. (2008 ▶). For a related structure, see: Wu et al. (2011 ▶). For the Top1 inhibitory activity of a related indolizinoquinoline-5,12-dione derivative, see: Wu et al. (2010 ▶).

Experimental

Crystal data

C18H11FN2O4

M = 338.29

Monoclinic,

a = 6.85562 (10) Å

b = 12.12898 (16) Å

c = 17.0304 (2) Å

β = 94.2306 (13)°

V = 1412.25 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.04 mm−1

T = 136 K

0.30 × 0.20 × 0.20 mm

Data collection

Agilent Xcalibur Onyx Nova diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.550, T max = 1.000

5740 measured reflections

2723 independent reflections

2278 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.08

2723 reflections

270 parameters

All H-atom parameters refined

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202692X/lh5489sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202692X/lh5489Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202692X/lh5489Isup3.cml

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

C18H11FN2O4	F(000) = 696
Mr = 338.29	Dx = 1.591 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 3543 reflections
a = 6.85562 (10) Å	θ = 2.6–72.7°
b = 12.12898 (16) Å	µ = 1.04 mm−1
c = 17.0304 (2) Å	T = 136 K
β = 94.2306 (13)°	Needle, orange
V = 1412.25 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Agilent Xcalibur Onyx Nova diffractometer	2723 independent reflections
Radiation source: Nova (Cu) X-ray Source	2278 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 8.2417 pixels mm-1	θmax = 72.9°, θmin = 5.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −14→10
Tmin = 0.550, Tmax = 1.000	l = −20→20
5740 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.8533P] where P = (Fo2 + 2Fc2)/3
2723 reflections	(Δ/σ)max = 0.001
270 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.24 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
F1	0.02823 (18)	0.90196 (9)	0.34624 (7)	0.0382 (3)
O2	0.28727 (18)	0.79052 (10)	0.60332 (7)	0.0266 (3)
O3	0.1029 (2)	0.36760 (11)	0.33751 (7)	0.0301 (3)
O1	0.3911 (2)	0.34756 (10)	0.58977 (7)	0.0307 (3)
N1	0.4460 (2)	0.68373 (12)	0.73454 (9)	0.0241 (3)
O4	0.2439 (2)	0.28907 (10)	0.44611 (8)	0.0291 (3)
C4	0.4124 (2)	0.51043 (14)	0.66509 (10)	0.0199 (4)
N2	0.1785 (2)	0.66666 (11)	0.45980 (8)	0.0195 (3)
C13	0.2564 (2)	0.62440 (14)	0.53105 (10)	0.0192 (4)
C6	0.2735 (2)	0.51065 (14)	0.52314 (10)	0.0193 (4)
C16	0.1782 (2)	0.37539 (14)	0.40402 (10)	0.0204 (4)
C14	0.3084 (2)	0.68974 (14)	0.60029 (10)	0.0199 (4)
C7	0.2028 (2)	0.48181 (14)	0.44537 (10)	0.0199 (4)
C5	0.3582 (2)	0.44629 (14)	0.59152 (10)	0.0202 (4)
C15	0.3912 (2)	0.62469 (14)	0.66995 (10)	0.0206 (4)
C12	0.1396 (3)	0.77509 (15)	0.44053 (11)	0.0238 (4)
C1	0.5239 (3)	0.62799 (15)	0.79713 (11)	0.0270 (4)
C10	0.0304 (3)	0.71363 (16)	0.30895 (11)	0.0286 (4)
C3	0.4925 (2)	0.45453 (15)	0.73164 (10)	0.0223 (4)
C18	0.2975 (3)	0.09848 (17)	0.46821 (13)	0.0328 (5)
C8	0.1448 (2)	0.58082 (14)	0.40663 (10)	0.0204 (4)
C2	0.5502 (3)	0.51463 (15)	0.79815 (11)	0.0253 (4)
C9	0.0689 (2)	0.60677 (15)	0.32938 (11)	0.0231 (4)
C17	0.2236 (3)	0.18208 (15)	0.40799 (12)	0.0265 (4)
C11	0.0667 (3)	0.79580 (15)	0.36591 (11)	0.0266 (4)
H1	0.568 (3)	0.6713 (18)	0.8436 (12)	0.028 (5)*
H17A	0.302 (3)	0.1835 (16)	0.3619 (12)	0.023 (5)*
H2	0.607 (3)	0.4777 (17)	0.8449 (12)	0.026 (5)*
H9	0.043 (3)	0.5454 (19)	0.2945 (13)	0.033 (6)*
H3	0.513 (3)	0.3732 (18)	0.7311 (12)	0.031 (5)*
H12	0.167 (3)	0.8305 (18)	0.4819 (13)	0.032 (6)*
H10	−0.018 (3)	0.7362 (18)	0.2575 (13)	0.034 (6)*
H17B	0.079 (3)	0.1699 (18)	0.3898 (12)	0.033 (6)*
H18A	0.439 (4)	0.117 (2)	0.4875 (15)	0.052 (7)*
H18B	0.217 (4)	0.099 (2)	0.5139 (15)	0.045 (7)*
H18C	0.291 (3)	0.022 (2)	0.4457 (13)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
F1	0.0529 (7)	0.0221 (6)	0.0372 (7)	0.0044 (5)	−0.0126 (5)	0.0072 (5)
O2	0.0321 (7)	0.0185 (6)	0.0281 (7)	0.0017 (5)	−0.0049 (5)	−0.0011 (5)
O3	0.0403 (7)	0.0246 (7)	0.0237 (7)	−0.0013 (6)	−0.0091 (6)	−0.0024 (5)
O1	0.0468 (8)	0.0173 (7)	0.0265 (7)	0.0026 (6)	−0.0071 (6)	0.0008 (5)
N1	0.0267 (8)	0.0217 (8)	0.0235 (8)	0.0003 (6)	−0.0008 (6)	−0.0025 (6)
O4	0.0408 (8)	0.0168 (6)	0.0278 (7)	0.0042 (6)	−0.0096 (6)	−0.0034 (5)
C4	0.0181 (8)	0.0186 (8)	0.0229 (9)	−0.0005 (6)	0.0003 (6)	−0.0009 (7)
N2	0.0178 (7)	0.0175 (7)	0.0229 (7)	0.0000 (5)	−0.0005 (5)	0.0003 (6)
C13	0.0175 (8)	0.0178 (8)	0.0218 (9)	0.0005 (6)	−0.0015 (6)	0.0025 (6)
C6	0.0169 (8)	0.0202 (8)	0.0208 (8)	0.0004 (6)	0.0009 (6)	−0.0008 (7)
C16	0.0165 (8)	0.0220 (9)	0.0227 (9)	−0.0015 (6)	0.0012 (6)	−0.0008 (7)
C14	0.0183 (8)	0.0160 (8)	0.0252 (9)	−0.0001 (6)	0.0010 (7)	−0.0008 (7)
C7	0.0173 (8)	0.0196 (8)	0.0223 (8)	−0.0005 (6)	−0.0016 (6)	−0.0004 (7)
C5	0.0201 (8)	0.0179 (9)	0.0225 (9)	−0.0007 (7)	0.0012 (7)	0.0019 (7)
C15	0.0212 (8)	0.0181 (8)	0.0219 (9)	−0.0023 (7)	−0.0010 (7)	−0.0002 (7)
C12	0.0235 (9)	0.0192 (9)	0.0284 (9)	0.0015 (7)	−0.0011 (7)	0.0025 (7)
C1	0.0330 (10)	0.0241 (9)	0.0231 (9)	−0.0005 (8)	−0.0046 (8)	−0.0025 (7)
C10	0.0277 (9)	0.0320 (10)	0.0251 (9)	0.0004 (8)	−0.0049 (7)	0.0037 (8)
C3	0.0230 (8)	0.0194 (9)	0.0243 (9)	−0.0006 (7)	0.0003 (7)	0.0020 (7)
C18	0.0386 (11)	0.0218 (10)	0.0375 (12)	0.0030 (8)	−0.0018 (9)	0.0016 (8)
C8	0.0174 (8)	0.0199 (9)	0.0237 (9)	−0.0011 (6)	−0.0001 (7)	−0.0002 (7)
C2	0.0297 (9)	0.0226 (9)	0.0229 (9)	0.0005 (7)	−0.0027 (7)	0.0028 (7)
C9	0.0219 (8)	0.0235 (9)	0.0234 (9)	−0.0002 (7)	−0.0023 (7)	0.0005 (7)
C17	0.0309 (10)	0.0186 (9)	0.0293 (10)	0.0002 (7)	−0.0023 (8)	−0.0053 (7)
C11	0.0286 (9)	0.0183 (9)	0.0320 (10)	0.0021 (7)	−0.0029 (8)	0.0069 (7)

F1—C11	1.352 (2)	C7—C8	1.413 (2)
O2—C14	1.232 (2)	C12—C11	1.354 (3)
O3—C16	1.213 (2)	C12—H12	0.98 (2)
O1—C5	1.219 (2)	C1—C2	1.387 (3)
N1—C15	1.343 (2)	C1—H1	0.98 (2)
N1—C1	1.339 (2)	C10—C9	1.363 (3)
O4—C16	1.329 (2)	C10—C11	1.400 (3)
O4—C17	1.453 (2)	C10—H10	0.95 (2)
C4—C5	1.498 (2)	C3—C2	1.380 (3)
C4—C15	1.397 (2)	C3—H3	1.00 (2)
C4—C3	1.398 (2)	C18—C17	1.503 (3)
N2—C13	1.387 (2)	C18—H18A	1.02 (3)
N2—C12	1.377 (2)	C18—H18B	0.99 (3)
N2—C8	1.388 (2)	C18—H18C	1.00 (2)
C13—C6	1.392 (2)	C8—C9	1.414 (2)
C13—C14	1.443 (2)	C2—H2	0.97 (2)
C6—C7	1.420 (2)	C9—H9	0.96 (2)
C6—C5	1.484 (2)	C17—H17A	0.98 (2)
C16—C7	1.474 (2)	C17—H17B	1.02 (2)
C14—C15	1.501 (2)
C1—N1—C15	116.99 (15)	N1—C1—H1	117.0 (12)
C16—O4—C17	116.44 (13)	C2—C1—H1	119.3 (12)
C15—C4—C5	122.98 (15)	C9—C10—C11	118.60 (17)
C15—C4—C3	118.01 (16)	C9—C10—H10	123.7 (14)
C3—C4—C5	118.99 (15)	C11—C10—H10	117.7 (13)
C13—N2—C8	109.17 (14)	C4—C3—H3	121.3 (12)
C12—N2—C13	128.08 (15)	C2—C3—C4	118.75 (16)
C12—N2—C8	122.75 (15)	C2—C3—H3	119.9 (12)
N2—C13—C6	108.13 (14)	C17—C18—H18A	109.7 (15)
N2—C13—C14	124.58 (15)	C17—C18—H18B	110.7 (14)
C6—C13—C14	127.29 (15)	C17—C18—H18C	111.0 (13)
C13—C6—C7	108.00 (15)	H18A—C18—H18B	109 (2)
C13—C6—C5	118.44 (15)	H18A—C18—H18C	109.6 (19)
C7—C6—C5	133.55 (16)	H18B—C18—H18C	107.2 (19)
O3—C16—O4	123.11 (16)	N2—C8—C7	107.77 (14)
O3—C16—C7	122.68 (16)	N2—C8—C9	118.18 (15)
O4—C16—C7	114.21 (14)	C7—C8—C9	134.04 (16)
O2—C14—C13	123.79 (16)	C1—C2—H2	120.8 (12)
O2—C14—C15	121.81 (15)	C3—C2—C1	118.96 (17)
C13—C14—C15	114.40 (14)	C3—C2—H2	120.2 (12)
C6—C7—C16	132.87 (15)	C10—C9—C8	120.02 (17)
C8—C7—C6	106.93 (14)	C10—C9—H9	123.8 (13)
C8—C7—C16	120.18 (15)	C8—C9—H9	116.1 (13)
O1—C5—C4	119.70 (15)	O4—C17—C18	106.34 (15)
O1—C5—C6	124.04 (16)	O4—C17—H17A	107.5 (12)
C6—C5—C4	116.21 (14)	O4—C17—H17B	108.8 (12)
N1—C15—C4	123.62 (16)	C18—C17—H17A	112.4 (11)
N1—C15—C14	115.71 (15)	C18—C17—H17B	112.2 (12)
C4—C15—C14	120.65 (15)	H17A—C17—H17B	109.3 (16)
N2—C12—H12	117.3 (13)	F1—C11—C12	117.46 (17)
C11—C12—N2	116.90 (17)	F1—C11—C10	118.99 (16)
C11—C12—H12	125.8 (13)	C12—C11—C10	123.55 (17)
N1—C1—C2	123.66 (17)
O2—C14—C15—N1	−2.0 (2)	C14—C13—C6—C5	−1.6 (3)
O2—C14—C15—C4	179.59 (17)	C7—C6—C5—O1	3.6 (3)
O3—C16—C7—C6	175.43 (17)	C7—C6—C5—C4	−179.07 (17)
O3—C16—C7—C8	−2.5 (3)	C7—C8—C9—C10	−178.48 (19)
N1—C1—C2—C3	−0.5 (3)	C5—C4—C15—N1	−177.38 (16)
O4—C16—C7—C6	−4.0 (3)	C5—C4—C15—C14	0.9 (3)
O4—C16—C7—C8	178.07 (15)	C5—C4—C3—C2	177.18 (16)
C4—C3—C2—C1	1.0 (3)	C5—C6—C7—C16	3.4 (3)
N2—C13—C6—C7	−0.53 (19)	C5—C6—C7—C8	−178.46 (17)
N2—C13—C6—C5	178.65 (14)	C15—N1—C1—C2	0.2 (3)
N2—C13—C14—O2	0.6 (3)	C15—C4—C5—O1	175.68 (17)
N2—C13—C14—C15	−179.64 (15)	C15—C4—C5—C6	−1.8 (2)
N2—C12—C11—F1	−179.88 (16)	C15—C4—C3—C2	−1.3 (2)
N2—C12—C11—C10	0.0 (3)	C12—N2—C13—C6	−178.91 (16)
N2—C8—C9—C10	−0.2 (3)	C12—N2—C13—C14	1.3 (3)
C13—N2—C12—C11	178.63 (17)	C12—N2—C8—C7	179.30 (15)
C13—N2—C8—C7	0.03 (18)	C12—N2—C8—C9	0.6 (2)
C13—N2—C8—C9	−178.66 (15)	C1—N1—C15—C4	−0.4 (3)
C13—C6—C7—C16	−177.61 (17)	C1—N1—C15—C14	−178.78 (16)
C13—C6—C7—C8	0.54 (19)	C3—C4—C5—O1	−2.7 (2)
C13—C6—C5—O1	−175.32 (17)	C3—C4—C5—C6	179.87 (15)
C13—C6—C5—C4	2.0 (2)	C3—C4—C15—N1	1.0 (3)
C13—C14—C15—N1	178.18 (15)	C3—C4—C15—C14	179.27 (15)
C13—C14—C15—C4	−0.2 (2)	C8—N2—C13—C6	0.31 (19)
C6—C13—C14—O2	−179.20 (17)	C8—N2—C13—C14	−179.48 (16)
C6—C13—C14—C15	0.6 (3)	C8—N2—C12—C11	−0.5 (3)
C6—C7—C8—N2	−0.35 (18)	C9—C10—C11—F1	−179.75 (17)
C6—C7—C8—C9	178.04 (18)	C9—C10—C11—C12	0.4 (3)
C16—O4—C17—C18	−177.06 (16)	C17—O4—C16—O3	0.8 (3)
C16—C7—C8—N2	178.08 (15)	C17—O4—C16—C7	−179.83 (15)
C16—C7—C8—C9	−3.5 (3)	C11—C10—C9—C8	−0.2 (3)
C14—C13—C6—C7	179.26 (16)