organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Ethyl 9-fluoro-5,12-dioxo-5,12-di­hydro­indolizino[2,3-g]quinoline-6-carboxyl­ate

aSchool of Pharmaceutical Science, Sun Yat-Sen University, Guangzhou 510006, People's Republic of China, and bSchool of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China
*Correspondence e-mail: lssalk@mail.sysu.edu.cn

(Received 4 June 2012; accepted 14 June 2012; online 25 July 2012)

In the title mol­ecule, C18H11FN2O4, the fused four- ring system is essentially planar, with an r.m.s. deviation of 0.032 Å. In the crystal, mol­ecules are connected by ππ stacking inter­actions [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[Pommier, Y. (2006). Nat. Rev. Cancer, 6, 789-802.]). For the synthesis, see: Shen et al. (2008[Shen, D. Q., Cheng, Y., An, L. K., Bu, X. Z., Huang, Z. S. & Gu, L. Q. (2008). Chin. Chem. Lett. 19, 533-536.]); Cheng et al. (2008[Cheng, Y., An, L. K., Wu, N., Wang, X. D., Bu, X. Z., Huang, Z. S. & Gu, L. Q. (2008). Bioorg. Med. Chem. 16, 4617-4625.]). For a related structure, see: Wu et al. (2011[Wu, X. W., Wu, Z. P., Wang, L. X., Zhang, H. B., Chen, J. W., Zhang, W., Gu, L. Q., Huang, Z. S. & An, L. K. (2011). Eur. J. Med. Chem. 46, 4625-4633.]). For the Top1 inhibitory activity of a related indolizinoquinoline-5,12-dione derivative, see: Wu et al. (2010[Wu, N., Wu, X. W., Agama, K., Pommier, Y., Du, J., Li, D., Gu, L. Q., Huang, Z. S. & An, L. K. (2010). Biochemistry, 49, 10131-10136.]).

[Scheme 1]

Experimental

Crystal data
  • C18H11FN2O4

  • Mr = 338.29

  • Monoclinic, P 21 /c

  • 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[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.550, Tmax = 1.000

  • 5740 measured reflections

  • 2723 independent reflections

  • 2278 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 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[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Top1 is an essential nuclear enzyme, and can be used as a target to discover anticancer agents (Pommier, 2006). In our previous research, we found ethyl 7-fluoro-5,12-dioxo-5,12-dihydroindolizino[2,3-g] quinoline-6-carboxylate is a strong Top1 inhibitor with a different inhibitory mechanism from camptothecin, a well known Top1 inhibitor (Wu et al. 2010). In order to investigate the Top1 inhibitory activity of the 9-fluoro substituted isomer, the title compound was synthesized according to a modified literature method (Shen et al. 2008; Cheng et al. 2008; Wu et al. 2011) and its crystal structure was determined.

The asymmetric unit of the title compound is shown in figure 1. In the molecule the four fused aromatic rings system is approximately planar with an r.m.s. deviation = 0.032 Å. In the crystal, molecules are connected by ππ stacking interactions to form chains along [100]. Cg1···Cg1i = 3.5684 (9)Å and Cg1···Cg4ii = 3.8247 (9) Å, where Cg1 and Cg2 are the centroids of the N2/C8/C7/C6/C13 and C4/C5/C6/C13/C14/C15 rings [symmetry codes: (i) -x, 1-y, 1-z, (ii) 1-x, 1-y, 1-z].

Related literature top

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 top

According to a modified literature method (Shen et al., 2008; Cheng et al., 2008; Wu et al., 2011), 12 equivalents of 3-fluoropyridine reacted with 6,7-dichloroquinoline-5,8-dione and ethyl acetoacetate to give the title compound as orange solid. Needle-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in chloroform-ethyl acetate (20/1, v/v).

Refinement top

All H atoms were refined indpendently with isotropic displacement parameters.

Structure description top

Top1 is an essential nuclear enzyme, and can be used as a target to discover anticancer agents (Pommier, 2006). In our previous research, we found ethyl 7-fluoro-5,12-dioxo-5,12-dihydroindolizino[2,3-g] quinoline-6-carboxylate is a strong Top1 inhibitor with a different inhibitory mechanism from camptothecin, a well known Top1 inhibitor (Wu et al. 2010). In order to investigate the Top1 inhibitory activity of the 9-fluoro substituted isomer, the title compound was synthesized according to a modified literature method (Shen et al. 2008; Cheng et al. 2008; Wu et al. 2011) and its crystal structure was determined.

The asymmetric unit of the title compound is shown in figure 1. In the molecule the four fused aromatic rings system is approximately planar with an r.m.s. deviation = 0.032 Å. In the crystal, molecules are connected by ππ stacking interactions to form chains along [100]. Cg1···Cg1i = 3.5684 (9)Å and Cg1···Cg4ii = 3.8247 (9) Å, where Cg1 and Cg2 are the centroids of the N2/C8/C7/C6/C13 and C4/C5/C6/C13/C14/C15 rings [symmetry codes: (i) -x, 1-y, 1-z, (ii) 1-x, 1-y, 1-z].

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. The displacement ellipsoids are at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
Ethyl 9-fluoro-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylate top
Crystal data top
C18H11FN2O4F(000) = 696
Mr = 338.29Dx = 1.591 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 3543 reflections
a = 6.85562 (10) Åθ = 2.6–72.7°
b = 12.12898 (16) ŵ = 1.04 mm1
c = 17.0304 (2) ÅT = 136 K
β = 94.2306 (13)°Needle, orange
V = 1412.25 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Agilent Xcalibur Onyx Nova
diffractometer
2723 independent reflections
Radiation source: Nova (Cu) X-ray Source2278 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.025
Detector resolution: 8.2417 pixels mm-1θmax = 72.9°, θmin = 5.2°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 1410
Tmin = 0.550, Tmax = 1.000l = 2020
5740 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101All 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 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C18H11FN2O4V = 1412.25 (3) Å3
Mr = 338.29Z = 4
Monoclinic, P21/cCu Kα radiation
a = 6.85562 (10) ŵ = 1.04 mm1
b = 12.12898 (16) ÅT = 136 K
c = 17.0304 (2) Å0.30 × 0.20 × 0.20 mm
β = 94.2306 (13)°
Data collection top
Agilent Xcalibur Onyx Nova
diffractometer
2723 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
2278 reflections with I > 2σ(I)
Tmin = 0.550, Tmax = 1.000Rint = 0.025
5740 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.101All H-atom parameters refined
S = 1.08Δρmax = 0.30 e Å3
2723 reflectionsΔρmin = 0.24 e Å3
270 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.02823 (18)0.90196 (9)0.34624 (7)0.0382 (3)
O20.28727 (18)0.79052 (10)0.60332 (7)0.0266 (3)
O30.1029 (2)0.36760 (11)0.33751 (7)0.0301 (3)
O10.3911 (2)0.34756 (10)0.58977 (7)0.0307 (3)
N10.4460 (2)0.68373 (12)0.73454 (9)0.0241 (3)
O40.2439 (2)0.28907 (10)0.44611 (8)0.0291 (3)
C40.4124 (2)0.51043 (14)0.66509 (10)0.0199 (4)
N20.1785 (2)0.66666 (11)0.45980 (8)0.0195 (3)
C130.2564 (2)0.62440 (14)0.53105 (10)0.0192 (4)
C60.2735 (2)0.51065 (14)0.52314 (10)0.0193 (4)
C160.1782 (2)0.37539 (14)0.40402 (10)0.0204 (4)
C140.3084 (2)0.68974 (14)0.60029 (10)0.0199 (4)
C70.2028 (2)0.48181 (14)0.44537 (10)0.0199 (4)
C50.3582 (2)0.44629 (14)0.59152 (10)0.0202 (4)
C150.3912 (2)0.62469 (14)0.66995 (10)0.0206 (4)
C120.1396 (3)0.77509 (15)0.44053 (11)0.0238 (4)
C10.5239 (3)0.62799 (15)0.79713 (11)0.0270 (4)
C100.0304 (3)0.71363 (16)0.30895 (11)0.0286 (4)
C30.4925 (2)0.45453 (15)0.73164 (10)0.0223 (4)
C180.2975 (3)0.09848 (17)0.46821 (13)0.0328 (5)
C80.1448 (2)0.58082 (14)0.40663 (10)0.0204 (4)
C20.5502 (3)0.51463 (15)0.79815 (11)0.0253 (4)
C90.0689 (2)0.60677 (15)0.32938 (11)0.0231 (4)
C170.2236 (3)0.18208 (15)0.40799 (12)0.0265 (4)
C110.0667 (3)0.79580 (15)0.36591 (11)0.0266 (4)
H10.568 (3)0.6713 (18)0.8436 (12)0.028 (5)*
H17A0.302 (3)0.1835 (16)0.3619 (12)0.023 (5)*
H20.607 (3)0.4777 (17)0.8449 (12)0.026 (5)*
H90.043 (3)0.5454 (19)0.2945 (13)0.033 (6)*
H30.513 (3)0.3732 (18)0.7311 (12)0.031 (5)*
H120.167 (3)0.8305 (18)0.4819 (13)0.032 (6)*
H100.018 (3)0.7362 (18)0.2575 (13)0.034 (6)*
H17B0.079 (3)0.1699 (18)0.3898 (12)0.033 (6)*
H18A0.439 (4)0.117 (2)0.4875 (15)0.052 (7)*
H18B0.217 (4)0.099 (2)0.5139 (15)0.045 (7)*
H18C0.291 (3)0.022 (2)0.4457 (13)0.039 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0529 (7)0.0221 (6)0.0372 (7)0.0044 (5)0.0126 (5)0.0072 (5)
O20.0321 (7)0.0185 (6)0.0281 (7)0.0017 (5)0.0049 (5)0.0011 (5)
O30.0403 (7)0.0246 (7)0.0237 (7)0.0013 (6)0.0091 (6)0.0024 (5)
O10.0468 (8)0.0173 (7)0.0265 (7)0.0026 (6)0.0071 (6)0.0008 (5)
N10.0267 (8)0.0217 (8)0.0235 (8)0.0003 (6)0.0008 (6)0.0025 (6)
O40.0408 (8)0.0168 (6)0.0278 (7)0.0042 (6)0.0096 (6)0.0034 (5)
C40.0181 (8)0.0186 (8)0.0229 (9)0.0005 (6)0.0003 (6)0.0009 (7)
N20.0178 (7)0.0175 (7)0.0229 (7)0.0000 (5)0.0005 (5)0.0003 (6)
C130.0175 (8)0.0178 (8)0.0218 (9)0.0005 (6)0.0015 (6)0.0025 (6)
C60.0169 (8)0.0202 (8)0.0208 (8)0.0004 (6)0.0009 (6)0.0008 (7)
C160.0165 (8)0.0220 (9)0.0227 (9)0.0015 (6)0.0012 (6)0.0008 (7)
C140.0183 (8)0.0160 (8)0.0252 (9)0.0001 (6)0.0010 (7)0.0008 (7)
C70.0173 (8)0.0196 (8)0.0223 (8)0.0005 (6)0.0016 (6)0.0004 (7)
C50.0201 (8)0.0179 (9)0.0225 (9)0.0007 (7)0.0012 (7)0.0019 (7)
C150.0212 (8)0.0181 (8)0.0219 (9)0.0023 (7)0.0010 (7)0.0002 (7)
C120.0235 (9)0.0192 (9)0.0284 (9)0.0015 (7)0.0011 (7)0.0025 (7)
C10.0330 (10)0.0241 (9)0.0231 (9)0.0005 (8)0.0046 (8)0.0025 (7)
C100.0277 (9)0.0320 (10)0.0251 (9)0.0004 (8)0.0049 (7)0.0037 (8)
C30.0230 (8)0.0194 (9)0.0243 (9)0.0006 (7)0.0003 (7)0.0020 (7)
C180.0386 (11)0.0218 (10)0.0375 (12)0.0030 (8)0.0018 (9)0.0016 (8)
C80.0174 (8)0.0199 (9)0.0237 (9)0.0011 (6)0.0001 (7)0.0002 (7)
C20.0297 (9)0.0226 (9)0.0229 (9)0.0005 (7)0.0027 (7)0.0028 (7)
C90.0219 (8)0.0235 (9)0.0234 (9)0.0002 (7)0.0023 (7)0.0005 (7)
C170.0309 (10)0.0186 (9)0.0293 (10)0.0002 (7)0.0023 (8)0.0053 (7)
C110.0286 (9)0.0183 (9)0.0320 (10)0.0021 (7)0.0029 (8)0.0069 (7)
Geometric parameters (Å, º) top
F1—C111.352 (2)C7—C81.413 (2)
O2—C141.232 (2)C12—C111.354 (3)
O3—C161.213 (2)C12—H120.98 (2)
O1—C51.219 (2)C1—C21.387 (3)
N1—C151.343 (2)C1—H10.98 (2)
N1—C11.339 (2)C10—C91.363 (3)
O4—C161.329 (2)C10—C111.400 (3)
O4—C171.453 (2)C10—H100.95 (2)
C4—C51.498 (2)C3—C21.380 (3)
C4—C151.397 (2)C3—H31.00 (2)
C4—C31.398 (2)C18—C171.503 (3)
N2—C131.387 (2)C18—H18A1.02 (3)
N2—C121.377 (2)C18—H18B0.99 (3)
N2—C81.388 (2)C18—H18C1.00 (2)
C13—C61.392 (2)C8—C91.414 (2)
C13—C141.443 (2)C2—H20.97 (2)
C6—C71.420 (2)C9—H90.96 (2)
C6—C51.484 (2)C17—H17A0.98 (2)
C16—C71.474 (2)C17—H17B1.02 (2)
C14—C151.501 (2)
C1—N1—C15116.99 (15)N1—C1—H1117.0 (12)
C16—O4—C17116.44 (13)C2—C1—H1119.3 (12)
C15—C4—C5122.98 (15)C9—C10—C11118.60 (17)
C15—C4—C3118.01 (16)C9—C10—H10123.7 (14)
C3—C4—C5118.99 (15)C11—C10—H10117.7 (13)
C13—N2—C8109.17 (14)C4—C3—H3121.3 (12)
C12—N2—C13128.08 (15)C2—C3—C4118.75 (16)
C12—N2—C8122.75 (15)C2—C3—H3119.9 (12)
N2—C13—C6108.13 (14)C17—C18—H18A109.7 (15)
N2—C13—C14124.58 (15)C17—C18—H18B110.7 (14)
C6—C13—C14127.29 (15)C17—C18—H18C111.0 (13)
C13—C6—C7108.00 (15)H18A—C18—H18B109 (2)
C13—C6—C5118.44 (15)H18A—C18—H18C109.6 (19)
C7—C6—C5133.55 (16)H18B—C18—H18C107.2 (19)
O3—C16—O4123.11 (16)N2—C8—C7107.77 (14)
O3—C16—C7122.68 (16)N2—C8—C9118.18 (15)
O4—C16—C7114.21 (14)C7—C8—C9134.04 (16)
O2—C14—C13123.79 (16)C1—C2—H2120.8 (12)
O2—C14—C15121.81 (15)C3—C2—C1118.96 (17)
C13—C14—C15114.40 (14)C3—C2—H2120.2 (12)
C6—C7—C16132.87 (15)C10—C9—C8120.02 (17)
C8—C7—C6106.93 (14)C10—C9—H9123.8 (13)
C8—C7—C16120.18 (15)C8—C9—H9116.1 (13)
O1—C5—C4119.70 (15)O4—C17—C18106.34 (15)
O1—C5—C6124.04 (16)O4—C17—H17A107.5 (12)
C6—C5—C4116.21 (14)O4—C17—H17B108.8 (12)
N1—C15—C4123.62 (16)C18—C17—H17A112.4 (11)
N1—C15—C14115.71 (15)C18—C17—H17B112.2 (12)
C4—C15—C14120.65 (15)H17A—C17—H17B109.3 (16)
N2—C12—H12117.3 (13)F1—C11—C12117.46 (17)
C11—C12—N2116.90 (17)F1—C11—C10118.99 (16)
C11—C12—H12125.8 (13)C12—C11—C10123.55 (17)
N1—C1—C2123.66 (17)
O2—C14—C15—N12.0 (2)C14—C13—C6—C51.6 (3)
O2—C14—C15—C4179.59 (17)C7—C6—C5—O13.6 (3)
O3—C16—C7—C6175.43 (17)C7—C6—C5—C4179.07 (17)
O3—C16—C7—C82.5 (3)C7—C8—C9—C10178.48 (19)
N1—C1—C2—C30.5 (3)C5—C4—C15—N1177.38 (16)
O4—C16—C7—C64.0 (3)C5—C4—C15—C140.9 (3)
O4—C16—C7—C8178.07 (15)C5—C4—C3—C2177.18 (16)
C4—C3—C2—C11.0 (3)C5—C6—C7—C163.4 (3)
N2—C13—C6—C70.53 (19)C5—C6—C7—C8178.46 (17)
N2—C13—C6—C5178.65 (14)C15—N1—C1—C20.2 (3)
N2—C13—C14—O20.6 (3)C15—C4—C5—O1175.68 (17)
N2—C13—C14—C15179.64 (15)C15—C4—C5—C61.8 (2)
N2—C12—C11—F1179.88 (16)C15—C4—C3—C21.3 (2)
N2—C12—C11—C100.0 (3)C12—N2—C13—C6178.91 (16)
N2—C8—C9—C100.2 (3)C12—N2—C13—C141.3 (3)
C13—N2—C12—C11178.63 (17)C12—N2—C8—C7179.30 (15)
C13—N2—C8—C70.03 (18)C12—N2—C8—C90.6 (2)
C13—N2—C8—C9178.66 (15)C1—N1—C15—C40.4 (3)
C13—C6—C7—C16177.61 (17)C1—N1—C15—C14178.78 (16)
C13—C6—C7—C80.54 (19)C3—C4—C5—O12.7 (2)
C13—C6—C5—O1175.32 (17)C3—C4—C5—C6179.87 (15)
C13—C6—C5—C42.0 (2)C3—C4—C15—N11.0 (3)
C13—C14—C15—N1178.18 (15)C3—C4—C15—C14179.27 (15)
C13—C14—C15—C40.2 (2)C8—N2—C13—C60.31 (19)
C6—C13—C14—O2179.20 (17)C8—N2—C13—C14179.48 (16)
C6—C13—C14—C150.6 (3)C8—N2—C12—C110.5 (3)
C6—C7—C8—N20.35 (18)C9—C10—C11—F1179.75 (17)
C6—C7—C8—C9178.04 (18)C9—C10—C11—C120.4 (3)
C16—O4—C17—C18177.06 (16)C17—O4—C16—O30.8 (3)
C16—C7—C8—N2178.08 (15)C17—O4—C16—C7179.83 (15)
C16—C7—C8—C93.5 (3)C11—C10—C9—C80.2 (3)
C14—C13—C6—C7179.26 (16)

Experimental details

Crystal data
Chemical formulaC18H11FN2O4
Mr338.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)136
a, b, c (Å)6.85562 (10), 12.12898 (16), 17.0304 (2)
β (°) 94.2306 (13)
V3)1412.25 (3)
Z4
Radiation typeCu Kα
µ (mm1)1.04
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerAgilent Xcalibur Onyx Nova
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.550, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
5740, 2723, 2278
Rint0.025
(sin θ/λ)max1)0.620
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.101, 1.08
No. of reflections2723
No. of parameters270
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.30, 0.24

Computer programs: CrysAlis PRO (Agilent, 2011), CrysAlis RED (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010).

 

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 30801425) and the Guangdong Natural Science Fund (No. 10151008901000022).

References

First citationAgilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.  Google Scholar
First citationCheng, Y., An, L. K., Wu, N., Wang, X. D., Bu, X. Z., Huang, Z. S. & Gu, L. Q. (2008). Bioorg. Med. Chem. 16, 4617–4625.  Web of Science CrossRef PubMed CAS Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationPommier, Y. (2006). Nat. Rev. Cancer, 6, 789–802.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShen, D. Q., Cheng, Y., An, L. K., Bu, X. Z., Huang, Z. S. & Gu, L. Q. (2008). Chin. Chem. Lett. 19, 533–536.  Web of Science CrossRef CAS Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, N., Wu, X. W., Agama, K., Pommier, Y., Du, J., Li, D., Gu, L. Q., Huang, Z. S. & An, L. K. (2010). Biochemistry, 49, 10131–10136.  Web of Science CrossRef CAS PubMed Google Scholar
First citationWu, X. W., Wu, Z. P., Wang, L. X., Zhang, H. B., Chen, J. W., Zhang, W., Gu, L. Q., Huang, Z. S. & An, L. K. (2011). Eur. J. Med. Chem. 46, 4625–4633.  Web of Science CSD CrossRef CAS PubMed Google Scholar

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