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In the title compound, C19H13NO5, the five fused rings are essentially coplanar, while one of the O—Me bonds lies almost perpendicular to that plane. The mol­ecule is stabilized by C—H...O inter­molecular hydrogen bonds, which form zigzag polymeric chains parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012195/sj6062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012195/sj6062Isup2.hkl
Contains datablock I

CCDC reference: 272109

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.051
  • wR factor = 0.144
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1A -C11A 1.45 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

8H-Benzo[g][1,3]benzodioxolo[6,5,4-de]quinolin-8-one top
Crystal data top
C19H13NO5F(000) = 696
Mr = 335.30Dx = 1.517 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.370 (2) ÅCell parameters from 808 reflections
b = 11.847 (3) Åθ = 2.2–1.5°
c = 14.825 (4) ŵ = 0.11 mm1
β = 93.096 (5)°T = 298 K
V = 1467.8 (7) Å3Block, orange–red
Z = 40.39 × 0.31 × 0.28 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2894 independent reflections
Radiation source: fine-focus sealed tube2142 reflections with I > 2σ(I)
Detector resolution: 83.66 pixels mm-1Rint = 0.023
ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 810
Tmin = 0.958, Tmax = 0.970k = 1414
8071 measured reflectionsl = 1818
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0801P)2 + 0.1614P]
where P = (Fo2 + 2Fc2)/3
2894 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.15 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.29835 (15)1.18225 (10)0.12171 (9)0.0513 (4)
O20.42115 (17)1.33849 (10)0.18600 (9)0.0552 (4)
O30.80385 (19)0.76981 (14)0.11369 (15)0.0951 (7)
O40.55491 (16)0.65775 (10)0.04145 (9)0.0520 (4)
N10.93520 (18)0.94488 (14)0.20062 (11)0.0535 (4)
C10.4527 (2)1.15551 (14)0.14706 (11)0.0391 (4)
C1A0.5274 (2)1.05327 (13)0.13989 (11)0.0362 (4)
C1B0.6915 (2)1.05211 (14)0.17355 (11)0.0375 (4)
C20.5278 (2)1.25129 (15)0.18647 (12)0.0441 (4)
C30.6794 (2)1.25201 (16)0.22083 (12)0.0488 (5)
H3A0.72551.31640.24700.059*
C3A0.7658 (2)1.14919 (15)0.21515 (12)0.0436 (5)
C40.9241 (2)1.13755 (19)0.24958 (14)0.0561 (5)
H4A0.97681.19820.27770.067*
C51.0003 (2)1.0368 (2)0.24151 (15)0.0603 (6)
H5A1.10471.03100.26600.072*
C6A0.7850 (2)0.95395 (15)0.16788 (12)0.0412 (4)
C70.7170 (2)0.85012 (16)0.12293 (13)0.0478 (5)
C7A0.5451 (2)0.85083 (14)0.09385 (11)0.0376 (4)
C80.4705 (2)0.75324 (14)0.05855 (11)0.0398 (4)
C90.3065 (2)0.75238 (15)0.03514 (12)0.0443 (4)
C100.2172 (2)0.84817 (16)0.04611 (12)0.0472 (5)
H10A0.10770.84730.03160.057*
C110.2897 (2)0.94572 (15)0.07858 (12)0.0432 (4)
H11A0.22821.01050.08420.052*
C11A0.4523 (2)0.94977 (13)0.10307 (11)0.0353 (4)
C120.2792 (3)1.30051 (16)0.13869 (14)0.0532 (5)
H12A0.26261.34120.08220.064*
H12B0.18741.31310.17470.064*
C130.5502 (3)0.57191 (17)0.10880 (15)0.0713 (7)
H13A0.61270.50840.09130.107*
H13B0.44150.54860.11500.107*
H13C0.59330.60100.16550.107*
C140.0831 (3)0.6502 (2)0.02828 (17)0.0721 (7)
H14A0.05550.57610.05000.108*
H14B0.06500.70400.07620.108*
H14C0.01800.66920.02090.108*
O50.24740 (17)0.65240 (11)0.00210 (10)0.0604 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0499 (8)0.0378 (7)0.0652 (8)0.0082 (6)0.0057 (7)0.0060 (6)
O20.0674 (9)0.0356 (7)0.0625 (9)0.0037 (6)0.0026 (7)0.0083 (6)
O30.0598 (11)0.0590 (11)0.1626 (18)0.0225 (8)0.0295 (11)0.0335 (11)
O40.0658 (9)0.0366 (7)0.0545 (8)0.0068 (6)0.0103 (6)0.0046 (6)
N10.0385 (9)0.0587 (11)0.0628 (10)0.0024 (7)0.0017 (8)0.0061 (8)
C10.0434 (10)0.0384 (10)0.0354 (9)0.0018 (8)0.0023 (7)0.0004 (7)
C1A0.0416 (10)0.0329 (9)0.0341 (8)0.0031 (7)0.0023 (7)0.0023 (7)
C1B0.0395 (10)0.0402 (10)0.0327 (8)0.0055 (7)0.0022 (7)0.0032 (7)
C20.0568 (12)0.0353 (10)0.0409 (9)0.0041 (8)0.0071 (8)0.0001 (8)
C30.0584 (12)0.0423 (11)0.0459 (10)0.0144 (9)0.0054 (9)0.0067 (8)
C3A0.0454 (11)0.0471 (11)0.0385 (9)0.0113 (8)0.0033 (8)0.0006 (8)
C40.0488 (12)0.0615 (13)0.0575 (12)0.0194 (10)0.0034 (9)0.0030 (10)
C50.0385 (11)0.0761 (15)0.0652 (13)0.0091 (10)0.0076 (9)0.0056 (12)
C6A0.0368 (10)0.0439 (10)0.0430 (10)0.0015 (8)0.0024 (7)0.0058 (8)
C70.0439 (11)0.0413 (10)0.0577 (11)0.0073 (8)0.0014 (9)0.0001 (9)
C7A0.0410 (10)0.0371 (9)0.0346 (8)0.0003 (7)0.0023 (7)0.0011 (7)
C80.0477 (10)0.0360 (9)0.0362 (9)0.0028 (8)0.0058 (7)0.0006 (7)
C90.0532 (11)0.0379 (10)0.0417 (9)0.0081 (8)0.0016 (8)0.0039 (8)
C100.0397 (10)0.0489 (11)0.0522 (11)0.0042 (8)0.0048 (8)0.0030 (9)
C110.0417 (10)0.0377 (10)0.0499 (10)0.0025 (8)0.0005 (8)0.0015 (8)
C11A0.0399 (10)0.0332 (9)0.0328 (8)0.0001 (7)0.0006 (7)0.0018 (7)
C120.0648 (14)0.0378 (11)0.0571 (12)0.0098 (9)0.0030 (10)0.0040 (9)
C130.1055 (19)0.0414 (12)0.0679 (14)0.0181 (11)0.0120 (13)0.0063 (10)
C140.0661 (16)0.0651 (15)0.0838 (16)0.0245 (12)0.0062 (12)0.0161 (13)
O50.0630 (10)0.0456 (8)0.0719 (10)0.0124 (6)0.0043 (7)0.0163 (7)
Geometric parameters (Å, º) top
O1—C11.364 (2)C5—H5A0.9300
O1—C121.434 (2)C6A—C71.497 (3)
O2—C21.365 (2)C7—C7A1.480 (2)
O2—C121.420 (2)C7A—C81.402 (2)
O3—C71.209 (2)C7A—C11A1.416 (2)
O4—C81.365 (2)C8—C91.397 (3)
O4—C131.427 (2)C9—O51.364 (2)
N1—C6A1.327 (2)C9—C101.373 (3)
N1—C51.347 (3)C10—C111.380 (2)
C1—C1A1.370 (2)C10—H10A0.9300
C1—C21.409 (2)C11—C11A1.390 (2)
C1A—C1B1.436 (2)C11—H11A0.9300
C1A—C11A1.469 (2)C12—H12A0.9700
C1B—C6A1.407 (2)C12—H12B0.9700
C1B—C3A1.431 (2)C13—H13A0.9600
C2—C31.341 (3)C13—H13B0.9600
C3—C3A1.421 (3)C13—H13C0.9600
C3—H3A0.9300C14—O51.424 (3)
C3A—C41.401 (3)C14—H14A0.9600
C4—C51.362 (3)C14—H14B0.9600
C4—H4A0.9300C14—H14C0.9600
C1—O1—C12106.98 (14)C11A—C7A—C7120.38 (15)
C2—O2—C12107.00 (14)O4—C8—C9117.34 (15)
C8—O4—C13115.26 (15)O4—C8—C7A121.90 (17)
C6A—N1—C5116.82 (17)C9—C8—C7A120.68 (15)
O1—C1—C1A127.86 (15)O5—C9—C10124.82 (17)
O1—C1—C2108.79 (15)O5—C9—C8115.31 (16)
C1A—C1—C2123.32 (17)C10—C9—C8119.87 (16)
C1—C1A—C1B114.42 (15)C9—C10—C11120.10 (17)
C1—C1A—C11A125.38 (16)C9—C10—H10A120.0
C1B—C1A—C11A120.20 (15)C11—C10—H10A120.0
C6A—C1B—C3A117.38 (16)C10—C11—C11A121.73 (16)
C6A—C1B—C1A120.79 (15)C10—C11—H11A119.1
C3A—C1B—C1A121.82 (16)C11A—C11—H11A119.1
C3—C2—O2127.02 (16)C11—C11A—C7A118.68 (15)
C3—C2—C1123.66 (17)C11—C11A—C1A121.24 (15)
O2—C2—C1109.29 (17)C7A—C11A—C1A120.06 (15)
C2—C3—C3A116.47 (16)O2—C12—O1107.32 (15)
C2—C3—H3A121.8O2—C12—H12A110.3
C3A—C3—H3A121.8O1—C12—H12A110.3
C4—C3A—C3122.48 (17)O2—C12—H12B110.3
C4—C3A—C1B117.27 (18)O1—C12—H12B110.3
C3—C3A—C1B120.25 (17)H12A—C12—H12B108.5
C5—C4—C3A119.51 (18)O4—C13—H13A109.5
C5—C4—H4A120.2O4—C13—H13B109.5
C3A—C4—H4A120.2H13A—C13—H13B109.5
N1—C5—C4124.63 (19)O4—C13—H13C109.5
N1—C5—H5A117.7H13A—C13—H13C109.5
C4—C5—H5A117.7H13B—C13—H13C109.5
N1—C6A—C1B124.34 (16)O5—C14—H14A109.5
N1—C6A—C7115.22 (15)O5—C14—H14B109.5
C1B—C6A—C7120.45 (16)H14A—C14—H14B109.5
O3—C7—C7A123.52 (17)O5—C14—H14C109.5
O3—C7—C6A118.74 (17)H14A—C14—H14C109.5
C7A—C7—C6A117.73 (15)H14B—C14—H14C109.5
C8—C7A—C11A118.91 (16)C9—O5—C14117.02 (16)
C8—C7A—C7120.70 (15)
C12—O1—C1—C1A177.19 (18)C1B—C6A—C7—O3175.0 (2)
C12—O1—C1—C24.81 (19)N1—C6A—C7—C7A173.55 (16)
O1—C1—C1A—C1B179.52 (15)C1B—C6A—C7—C7A6.3 (3)
C2—C1—C1A—C1B1.8 (2)O3—C7—C7A—C84.2 (3)
O1—C1—C1A—C11A0.6 (3)C6A—C7—C7A—C8174.40 (15)
C2—C1—C1A—C11A177.15 (16)O3—C7—C7A—C11A177.1 (2)
C1—C1A—C1B—C6A177.86 (15)C6A—C7—C7A—C11A4.3 (2)
C11A—C1A—C1B—C6A3.1 (2)C13—O4—C8—C983.5 (2)
C1—C1A—C1B—C3A3.1 (2)C13—O4—C8—C7A99.7 (2)
C11A—C1A—C1B—C3A175.93 (15)C11A—C7A—C8—O4174.92 (14)
C12—O2—C2—C3177.16 (18)C7—C7A—C8—O46.4 (3)
C12—O2—C2—C14.8 (2)C11A—C7A—C8—C91.8 (2)
O1—C1—C2—C3178.08 (16)C7—C7A—C8—C9176.91 (16)
C1A—C1—C2—C30.0 (3)O4—C8—C9—O53.6 (2)
O1—C1—C2—O20.0 (2)C7A—C8—C9—O5179.56 (15)
C1A—C1—C2—O2178.14 (15)O4—C8—C9—C10176.36 (16)
O2—C2—C3—C3A178.41 (17)C7A—C8—C9—C100.5 (3)
C1—C2—C3—C3A0.6 (3)O5—C9—C10—C11178.75 (17)
C2—C3—C3A—C4178.97 (17)C8—C9—C10—C111.2 (3)
C2—C3—C3A—C1B0.7 (3)C9—C10—C11—C11A1.6 (3)
C6A—C1B—C3A—C42.1 (2)C10—C11—C11A—C7A0.3 (3)
C1A—C1B—C3A—C4177.04 (16)C10—C11—C11A—C1A178.32 (17)
C6A—C1B—C3A—C3178.26 (16)C8—C7A—C11A—C111.4 (2)
C1A—C1B—C3A—C32.6 (3)C7—C7A—C11A—C11177.29 (16)
C3—C3A—C4—C5179.67 (19)C8—C7A—C11A—C1A180.00 (15)
C1B—C3A—C4—C50.7 (3)C7—C7A—C11A—C1A1.3 (2)
C6A—N1—C5—C41.4 (3)C1—C1A—C11A—C115.5 (3)
C3A—C4—C5—N11.2 (3)C1B—C1A—C11A—C11173.40 (15)
C5—N1—C6A—C1B0.2 (3)C1—C1A—C11A—C7A175.95 (15)
C5—N1—C6A—C7179.97 (17)C1B—C1A—C11A—C7A5.2 (2)
C3A—C1B—C6A—N11.9 (3)C2—O2—C12—O17.7 (2)
C1A—C1B—C6A—N1177.20 (16)C1—O1—C12—O27.7 (2)
C3A—C1B—C6A—C7178.25 (15)C10—C9—O5—C144.1 (3)
C1A—C1B—C6A—C72.6 (2)C8—C9—O5—C14175.84 (17)
N1—C6A—C7—O35.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O10.932.182.874 (2)131
C13—H13B···O50.962.583.066 (3)112
C4—H4A···O3i0.932.523.354 (3)149
C12—H12A···O4ii0.972.453.115 (3)126
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+1, y+2, z.
 

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