In the title compound, C
19H
13NO
5, 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
CCDC reference: 272109
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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).
8
H-Benzo[
g][1,3]benzodioxolo[6,5,4-de]quinolin-8-one
top
Crystal data top
C19H13NO5 | F(000) = 696 |
Mr = 335.30 | Dx = 1.517 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.370 (2) Å | Cell parameters from 808 reflections |
b = 11.847 (3) Å | θ = 2.2–1.5° |
c = 14.825 (4) Å | µ = 0.11 mm−1 |
β = 93.096 (5)° | T = 298 K |
V = 1467.8 (7) Å3 | Block, orange–red |
Z = 4 | 0.39 × 0.31 × 0.28 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2894 independent reflections |
Radiation source: fine-focus sealed tube | 2142 reflections with I > 2σ(I) |
Detector resolution: 83.66 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→10 |
Tmin = 0.958, Tmax = 0.970 | k = −14→14 |
8071 measured reflections | l = −18→18 |
Refinement top
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.29835 (15) | 1.18225 (10) | 0.12171 (9) | 0.0513 (4) | |
O2 | 0.42115 (17) | 1.33849 (10) | 0.18600 (9) | 0.0552 (4) | |
O3 | 0.80385 (19) | 0.76981 (14) | 0.11369 (15) | 0.0951 (7) | |
O4 | 0.55491 (16) | 0.65775 (10) | 0.04145 (9) | 0.0520 (4) | |
N1 | 0.93520 (18) | 0.94488 (14) | 0.20062 (11) | 0.0535 (4) | |
C1 | 0.4527 (2) | 1.15551 (14) | 0.14706 (11) | 0.0391 (4) | |
C1A | 0.5274 (2) | 1.05327 (13) | 0.13989 (11) | 0.0362 (4) | |
C1B | 0.6915 (2) | 1.05211 (14) | 0.17355 (11) | 0.0375 (4) | |
C2 | 0.5278 (2) | 1.25129 (15) | 0.18647 (12) | 0.0441 (4) | |
C3 | 0.6794 (2) | 1.25201 (16) | 0.22083 (12) | 0.0488 (5) | |
H3A | 0.7255 | 1.3164 | 0.2470 | 0.059* | |
C3A | 0.7658 (2) | 1.14919 (15) | 0.21515 (12) | 0.0436 (5) | |
C4 | 0.9241 (2) | 1.13755 (19) | 0.24958 (14) | 0.0561 (5) | |
H4A | 0.9768 | 1.1982 | 0.2777 | 0.067* | |
C5 | 1.0003 (2) | 1.0368 (2) | 0.24151 (15) | 0.0603 (6) | |
H5A | 1.1047 | 1.0310 | 0.2660 | 0.072* | |
C6A | 0.7850 (2) | 0.95395 (15) | 0.16788 (12) | 0.0412 (4) | |
C7 | 0.7170 (2) | 0.85012 (16) | 0.12293 (13) | 0.0478 (5) | |
C7A | 0.5451 (2) | 0.85083 (14) | 0.09385 (11) | 0.0376 (4) | |
C8 | 0.4705 (2) | 0.75324 (14) | 0.05855 (11) | 0.0398 (4) | |
C9 | 0.3065 (2) | 0.75238 (15) | 0.03514 (12) | 0.0443 (4) | |
C10 | 0.2172 (2) | 0.84817 (16) | 0.04611 (12) | 0.0472 (5) | |
H10A | 0.1077 | 0.8473 | 0.0316 | 0.057* | |
C11 | 0.2897 (2) | 0.94572 (15) | 0.07858 (12) | 0.0432 (4) | |
H11A | 0.2282 | 1.0105 | 0.0842 | 0.052* | |
C11A | 0.4523 (2) | 0.94977 (13) | 0.10307 (11) | 0.0353 (4) | |
C12 | 0.2792 (3) | 1.30051 (16) | 0.13869 (14) | 0.0532 (5) | |
H12A | 0.2626 | 1.3412 | 0.0822 | 0.064* | |
H12B | 0.1874 | 1.3131 | 0.1747 | 0.064* | |
C13 | 0.5502 (3) | 0.57191 (17) | 0.10880 (15) | 0.0713 (7) | |
H13A | 0.6127 | 0.5084 | 0.0913 | 0.107* | |
H13B | 0.4415 | 0.5486 | 0.1150 | 0.107* | |
H13C | 0.5933 | 0.6010 | 0.1655 | 0.107* | |
C14 | 0.0831 (3) | 0.6502 (2) | −0.02828 (17) | 0.0721 (7) | |
H14A | 0.0555 | 0.5761 | −0.0500 | 0.108* | |
H14B | 0.0650 | 0.7040 | −0.0762 | 0.108* | |
H14C | 0.0180 | 0.6692 | 0.0209 | 0.108* | |
O5 | 0.24740 (17) | 0.65240 (11) | 0.00210 (10) | 0.0604 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0499 (8) | 0.0378 (7) | 0.0652 (8) | 0.0082 (6) | −0.0057 (7) | −0.0060 (6) |
O2 | 0.0674 (9) | 0.0356 (7) | 0.0625 (9) | 0.0037 (6) | 0.0026 (7) | −0.0083 (6) |
O3 | 0.0598 (11) | 0.0590 (11) | 0.1626 (18) | 0.0225 (8) | −0.0295 (11) | −0.0335 (11) |
O4 | 0.0658 (9) | 0.0366 (7) | 0.0545 (8) | 0.0068 (6) | 0.0103 (6) | −0.0046 (6) |
N1 | 0.0385 (9) | 0.0587 (11) | 0.0628 (10) | −0.0024 (7) | −0.0017 (8) | 0.0061 (8) |
C1 | 0.0434 (10) | 0.0384 (10) | 0.0354 (9) | −0.0018 (8) | 0.0023 (7) | 0.0004 (7) |
C1A | 0.0416 (10) | 0.0329 (9) | 0.0341 (8) | −0.0031 (7) | 0.0023 (7) | 0.0023 (7) |
C1B | 0.0395 (10) | 0.0402 (10) | 0.0327 (8) | −0.0055 (7) | 0.0022 (7) | 0.0032 (7) |
C2 | 0.0568 (12) | 0.0353 (10) | 0.0409 (9) | −0.0041 (8) | 0.0071 (8) | 0.0001 (8) |
C3 | 0.0584 (12) | 0.0423 (11) | 0.0459 (10) | −0.0144 (9) | 0.0054 (9) | −0.0067 (8) |
C3A | 0.0454 (11) | 0.0471 (11) | 0.0385 (9) | −0.0113 (8) | 0.0033 (8) | −0.0006 (8) |
C4 | 0.0488 (12) | 0.0615 (13) | 0.0575 (12) | −0.0194 (10) | −0.0034 (9) | −0.0030 (10) |
C5 | 0.0385 (11) | 0.0761 (15) | 0.0652 (13) | −0.0091 (10) | −0.0076 (9) | 0.0056 (12) |
C6A | 0.0368 (10) | 0.0439 (10) | 0.0430 (10) | −0.0015 (8) | 0.0024 (7) | 0.0058 (8) |
C7 | 0.0439 (11) | 0.0413 (10) | 0.0577 (11) | 0.0073 (8) | −0.0014 (9) | −0.0001 (9) |
C7A | 0.0410 (10) | 0.0371 (9) | 0.0346 (8) | −0.0003 (7) | 0.0023 (7) | 0.0011 (7) |
C8 | 0.0477 (10) | 0.0360 (9) | 0.0362 (9) | 0.0028 (8) | 0.0058 (7) | −0.0006 (7) |
C9 | 0.0532 (11) | 0.0379 (10) | 0.0417 (9) | −0.0081 (8) | 0.0016 (8) | −0.0039 (8) |
C10 | 0.0397 (10) | 0.0489 (11) | 0.0522 (11) | −0.0042 (8) | −0.0048 (8) | −0.0030 (9) |
C11 | 0.0417 (10) | 0.0377 (10) | 0.0499 (10) | 0.0025 (8) | −0.0005 (8) | −0.0015 (8) |
C11A | 0.0399 (10) | 0.0332 (9) | 0.0328 (8) | 0.0001 (7) | 0.0006 (7) | 0.0018 (7) |
C12 | 0.0648 (14) | 0.0378 (11) | 0.0571 (12) | 0.0098 (9) | 0.0030 (10) | −0.0040 (9) |
C13 | 0.1055 (19) | 0.0414 (12) | 0.0679 (14) | 0.0181 (11) | 0.0120 (13) | 0.0063 (10) |
C14 | 0.0661 (16) | 0.0651 (15) | 0.0838 (16) | −0.0245 (12) | −0.0062 (12) | −0.0161 (13) |
O5 | 0.0630 (10) | 0.0456 (8) | 0.0719 (10) | −0.0124 (6) | −0.0043 (7) | −0.0163 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.364 (2) | C5—H5A | 0.9300 |
O1—C12 | 1.434 (2) | C6A—C7 | 1.497 (3) |
O2—C2 | 1.365 (2) | C7—C7A | 1.480 (2) |
O2—C12 | 1.420 (2) | C7A—C8 | 1.402 (2) |
O3—C7 | 1.209 (2) | C7A—C11A | 1.416 (2) |
O4—C8 | 1.365 (2) | C8—C9 | 1.397 (3) |
O4—C13 | 1.427 (2) | C9—O5 | 1.364 (2) |
N1—C6A | 1.327 (2) | C9—C10 | 1.373 (3) |
N1—C5 | 1.347 (3) | C10—C11 | 1.380 (2) |
C1—C1A | 1.370 (2) | C10—H10A | 0.9300 |
C1—C2 | 1.409 (2) | C11—C11A | 1.390 (2) |
C1A—C1B | 1.436 (2) | C11—H11A | 0.9300 |
C1A—C11A | 1.469 (2) | C12—H12A | 0.9700 |
C1B—C6A | 1.407 (2) | C12—H12B | 0.9700 |
C1B—C3A | 1.431 (2) | C13—H13A | 0.9600 |
C2—C3 | 1.341 (3) | C13—H13B | 0.9600 |
C3—C3A | 1.421 (3) | C13—H13C | 0.9600 |
C3—H3A | 0.9300 | C14—O5 | 1.424 (3) |
C3A—C4 | 1.401 (3) | C14—H14A | 0.9600 |
C4—C5 | 1.362 (3) | C14—H14B | 0.9600 |
C4—H4A | 0.9300 | C14—H14C | 0.9600 |
| | | |
C1—O1—C12 | 106.98 (14) | C11A—C7A—C7 | 120.38 (15) |
C2—O2—C12 | 107.00 (14) | O4—C8—C9 | 117.34 (15) |
C8—O4—C13 | 115.26 (15) | O4—C8—C7A | 121.90 (17) |
C6A—N1—C5 | 116.82 (17) | C9—C8—C7A | 120.68 (15) |
O1—C1—C1A | 127.86 (15) | O5—C9—C10 | 124.82 (17) |
O1—C1—C2 | 108.79 (15) | O5—C9—C8 | 115.31 (16) |
C1A—C1—C2 | 123.32 (17) | C10—C9—C8 | 119.87 (16) |
C1—C1A—C1B | 114.42 (15) | C9—C10—C11 | 120.10 (17) |
C1—C1A—C11A | 125.38 (16) | C9—C10—H10A | 120.0 |
C1B—C1A—C11A | 120.20 (15) | C11—C10—H10A | 120.0 |
C6A—C1B—C3A | 117.38 (16) | C10—C11—C11A | 121.73 (16) |
C6A—C1B—C1A | 120.79 (15) | C10—C11—H11A | 119.1 |
C3A—C1B—C1A | 121.82 (16) | C11A—C11—H11A | 119.1 |
C3—C2—O2 | 127.02 (16) | C11—C11A—C7A | 118.68 (15) |
C3—C2—C1 | 123.66 (17) | C11—C11A—C1A | 121.24 (15) |
O2—C2—C1 | 109.29 (17) | C7A—C11A—C1A | 120.06 (15) |
C2—C3—C3A | 116.47 (16) | O2—C12—O1 | 107.32 (15) |
C2—C3—H3A | 121.8 | O2—C12—H12A | 110.3 |
C3A—C3—H3A | 121.8 | O1—C12—H12A | 110.3 |
C4—C3A—C3 | 122.48 (17) | O2—C12—H12B | 110.3 |
C4—C3A—C1B | 117.27 (18) | O1—C12—H12B | 110.3 |
C3—C3A—C1B | 120.25 (17) | H12A—C12—H12B | 108.5 |
C5—C4—C3A | 119.51 (18) | O4—C13—H13A | 109.5 |
C5—C4—H4A | 120.2 | O4—C13—H13B | 109.5 |
C3A—C4—H4A | 120.2 | H13A—C13—H13B | 109.5 |
N1—C5—C4 | 124.63 (19) | O4—C13—H13C | 109.5 |
N1—C5—H5A | 117.7 | H13A—C13—H13C | 109.5 |
C4—C5—H5A | 117.7 | H13B—C13—H13C | 109.5 |
N1—C6A—C1B | 124.34 (16) | O5—C14—H14A | 109.5 |
N1—C6A—C7 | 115.22 (15) | O5—C14—H14B | 109.5 |
C1B—C6A—C7 | 120.45 (16) | H14A—C14—H14B | 109.5 |
O3—C7—C7A | 123.52 (17) | O5—C14—H14C | 109.5 |
O3—C7—C6A | 118.74 (17) | H14A—C14—H14C | 109.5 |
C7A—C7—C6A | 117.73 (15) | H14B—C14—H14C | 109.5 |
C8—C7A—C11A | 118.91 (16) | C9—O5—C14 | 117.02 (16) |
C8—C7A—C7 | 120.70 (15) | | |
| | | |
C12—O1—C1—C1A | −177.19 (18) | C1B—C6A—C7—O3 | 175.0 (2) |
C12—O1—C1—C2 | 4.81 (19) | N1—C6A—C7—C7A | 173.55 (16) |
O1—C1—C1A—C1B | −179.52 (15) | C1B—C6A—C7—C7A | −6.3 (3) |
C2—C1—C1A—C1B | −1.8 (2) | O3—C7—C7A—C8 | 4.2 (3) |
O1—C1—C1A—C11A | −0.6 (3) | C6A—C7—C7A—C8 | −174.40 (15) |
C2—C1—C1A—C11A | 177.15 (16) | O3—C7—C7A—C11A | −177.1 (2) |
C1—C1A—C1B—C6A | −177.86 (15) | C6A—C7—C7A—C11A | 4.3 (2) |
C11A—C1A—C1B—C6A | 3.1 (2) | C13—O4—C8—C9 | −83.5 (2) |
C1—C1A—C1B—C3A | 3.1 (2) | C13—O4—C8—C7A | 99.7 (2) |
C11A—C1A—C1B—C3A | −175.93 (15) | C11A—C7A—C8—O4 | 174.92 (14) |
C12—O2—C2—C3 | 177.16 (18) | C7—C7A—C8—O4 | −6.4 (3) |
C12—O2—C2—C1 | −4.8 (2) | C11A—C7A—C8—C9 | −1.8 (2) |
O1—C1—C2—C3 | 178.08 (16) | C7—C7A—C8—C9 | 176.91 (16) |
C1A—C1—C2—C3 | 0.0 (3) | O4—C8—C9—O5 | 3.6 (2) |
O1—C1—C2—O2 | 0.0 (2) | C7A—C8—C9—O5 | −179.56 (15) |
C1A—C1—C2—O2 | −178.14 (15) | O4—C8—C9—C10 | −176.36 (16) |
O2—C2—C3—C3A | 178.41 (17) | C7A—C8—C9—C10 | 0.5 (3) |
C1—C2—C3—C3A | 0.6 (3) | O5—C9—C10—C11 | −178.75 (17) |
C2—C3—C3A—C4 | −178.97 (17) | C8—C9—C10—C11 | 1.2 (3) |
C2—C3—C3A—C1B | 0.7 (3) | C9—C10—C11—C11A | −1.6 (3) |
C6A—C1B—C3A—C4 | −2.1 (2) | C10—C11—C11A—C7A | 0.3 (3) |
C1A—C1B—C3A—C4 | 177.04 (16) | C10—C11—C11A—C1A | −178.32 (17) |
C6A—C1B—C3A—C3 | 178.26 (16) | C8—C7A—C11A—C11 | 1.4 (2) |
C1A—C1B—C3A—C3 | −2.6 (3) | C7—C7A—C11A—C11 | −177.29 (16) |
C3—C3A—C4—C5 | −179.67 (19) | C8—C7A—C11A—C1A | 180.00 (15) |
C1B—C3A—C4—C5 | 0.7 (3) | C7—C7A—C11A—C1A | 1.3 (2) |
C6A—N1—C5—C4 | −1.4 (3) | C1—C1A—C11A—C11 | −5.5 (3) |
C3A—C4—C5—N1 | 1.2 (3) | C1B—C1A—C11A—C11 | 173.40 (15) |
C5—N1—C6A—C1B | −0.2 (3) | C1—C1A—C11A—C7A | 175.95 (15) |
C5—N1—C6A—C7 | 179.97 (17) | C1B—C1A—C11A—C7A | −5.2 (2) |
C3A—C1B—C6A—N1 | 1.9 (3) | C2—O2—C12—O1 | 7.7 (2) |
C1A—C1B—C6A—N1 | −177.20 (16) | C1—O1—C12—O2 | −7.7 (2) |
C3A—C1B—C6A—C7 | −178.25 (15) | C10—C9—O5—C14 | 4.1 (3) |
C1A—C1B—C6A—C7 | 2.6 (2) | C8—C9—O5—C14 | −175.84 (17) |
N1—C6A—C7—O3 | −5.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···O1 | 0.93 | 2.18 | 2.874 (2) | 131 |
C13—H13B···O5 | 0.96 | 2.58 | 3.066 (3) | 112 |
C4—H4A···O3i | 0.93 | 2.52 | 3.354 (3) | 149 |
C12—H12A···O4ii | 0.97 | 2.45 | 3.115 (3) | 126 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, −y+2, −z. |