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In the title compound, C12H15NO3, the iso­quinoline moiety is essentially planar, except for the N and adjacent Csp3 atoms, which deviate from the mean plane by 0.198 (2) and 0.686 (2) Å, respectively. The bond length between the N and carbonyl C atoms [1.353 (3) Å] is close to a double-bond value, indicating electron delocalization. No significant intermolecular interactions are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005787/cv6461sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005787/cv6461Isup2.hkl
Contains datablock I

CCDC reference: 270283

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.145
  • Data-to-parameter ratio = 15.8

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 ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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).

6,7-Dimethoxy-2-methyl-3,4-dihydroisoquinolin-1(2H)-one top
Crystal data top
C12H15NO3F(000) = 472
Mr = 221.25Dx = 1.331 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.7846 (17) ÅCell parameters from 912 reflections
b = 16.865 (3) Åθ = 2.1–26.5°
c = 6.8914 (12) ŵ = 0.10 mm1
β = 103.934 (3)°T = 273 K
V = 1103.7 (3) Å3Plate, colourless
Z = 40.31 × 0.11 × 0.06 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2285 independent reflections
Radiation source: fine-focus sealed tube1673 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 83.66 pixels mm-1θmax = 26.5°, θmin = 2.1°
ω scansh = 1012
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2120
Tmin = 0.971, Tmax = 0.994l = 68
6118 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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2375P]
where P = (Fo2 + 2Fc2)/3
2285 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.15 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.56580 (17)0.08915 (10)0.2136 (2)0.0672 (5)
O21.01861 (15)0.17575 (8)0.5321 (2)0.0620 (4)
O30.85128 (16)0.16425 (9)0.1858 (2)0.0649 (5)
N20.60556 (18)0.11541 (10)0.5436 (3)0.0571 (5)
C10.6259 (2)0.07281 (12)0.3866 (3)0.0504 (5)
C30.6599 (2)0.08909 (14)0.7492 (3)0.0615 (6)
H3A0.65880.13320.83920.074*
H3B0.59920.04790.77990.074*
C40.8069 (2)0.05778 (13)0.7825 (3)0.0570 (5)
H4A0.87130.10130.78060.068*
H4B0.83400.03260.91270.068*
C50.9155 (2)0.06187 (12)0.6580 (3)0.0494 (5)
H5A0.97620.06690.78400.059*
C60.9255 (2)0.11468 (11)0.5105 (3)0.0478 (5)
C70.8338 (2)0.10780 (12)0.3194 (3)0.0478 (5)
C80.73702 (19)0.04734 (11)0.2833 (3)0.0461 (5)
H8A0.67690.04200.15710.055*
C90.7280 (2)0.00628 (11)0.4345 (3)0.0452 (5)
C100.8168 (2)0.00121 (11)0.6231 (3)0.0460 (5)
C110.5020 (3)0.17871 (14)0.5088 (4)0.0732 (7)
H11A0.47470.19050.36850.110*
H11B0.42080.16230.55370.110*
H11C0.54200.22520.58120.110*
C121.1050 (2)0.19050 (14)0.7269 (3)0.0670 (6)
H12A1.16560.23480.72190.100*
H12B1.16120.14450.77310.100*
H12C1.04660.20210.81690.100*
C130.7513 (2)0.16698 (14)0.0011 (3)0.0614 (6)
H13A0.77500.20890.07920.092*
H13B0.65960.17660.02350.092*
H13C0.75100.11730.06700.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0702 (10)0.0759 (11)0.0495 (9)0.0194 (8)0.0025 (7)0.0059 (7)
O20.0592 (9)0.0580 (9)0.0606 (9)0.0125 (7)0.0017 (7)0.0025 (7)
O30.0604 (9)0.0709 (10)0.0561 (9)0.0139 (8)0.0003 (7)0.0159 (7)
N20.0579 (11)0.0601 (11)0.0534 (11)0.0112 (9)0.0137 (8)0.0005 (8)
C10.0462 (11)0.0550 (12)0.0489 (12)0.0007 (9)0.0092 (9)0.0043 (9)
C30.0645 (14)0.0710 (15)0.0487 (12)0.0042 (11)0.0134 (10)0.0067 (10)
C40.0594 (13)0.0606 (13)0.0486 (12)0.0006 (10)0.0081 (10)0.0049 (10)
C50.0470 (11)0.0550 (12)0.0414 (10)0.0044 (9)0.0011 (8)0.0021 (9)
C60.0423 (10)0.0466 (11)0.0515 (11)0.0001 (8)0.0055 (9)0.0048 (9)
C70.0444 (11)0.0525 (12)0.0453 (11)0.0035 (9)0.0084 (8)0.0041 (9)
C80.0418 (10)0.0540 (12)0.0395 (10)0.0021 (9)0.0041 (8)0.0023 (8)
C90.0435 (10)0.0479 (11)0.0446 (10)0.0029 (8)0.0112 (8)0.0033 (8)
C100.0440 (10)0.0484 (11)0.0445 (11)0.0046 (8)0.0085 (9)0.0006 (8)
C110.0754 (16)0.0715 (16)0.0732 (16)0.0216 (13)0.0190 (13)0.0015 (12)
C120.0572 (13)0.0631 (14)0.0702 (15)0.0094 (11)0.0048 (11)0.0120 (11)
C130.0659 (14)0.0655 (14)0.0480 (12)0.0046 (11)0.0044 (10)0.0092 (10)
Geometric parameters (Å, º) top
O1—C11.227 (2)C5—C101.388 (3)
O2—C61.359 (2)C5—H5A0.9300
O2—C121.426 (2)C6—C71.409 (3)
O3—C71.364 (2)C7—C81.373 (3)
O3—C131.407 (2)C8—C91.398 (3)
N2—C11.353 (3)C8—H8A0.9300
N2—C111.451 (3)C9—C101.385 (3)
N2—C31.458 (3)C11—H11A0.9600
C1—C91.486 (3)C11—H11B0.9600
C3—C41.497 (3)C11—H11C0.9600
C3—H3A0.9700C12—H12A0.9600
C3—H3B0.9700C12—H12B0.9600
C4—C101.502 (3)C12—H12C0.9600
C4—H4A0.9700C13—H13A0.9600
C4—H4B0.9700C13—H13B0.9600
C5—C61.373 (3)C13—H13C0.9600
C6—O2—C12117.75 (16)C8—C7—C6119.15 (17)
C7—O3—C13117.41 (16)C7—C8—C9120.68 (17)
C1—N2—C11119.30 (18)C7—C8—H8A119.7
C1—N2—C3121.76 (17)C9—C8—H8A119.7
C11—N2—C3117.48 (17)C10—C9—C8120.16 (18)
O1—C1—N2121.99 (19)C10—C9—C1120.92 (17)
O1—C1—C9121.63 (18)C8—C9—C1118.88 (17)
N2—C1—C9116.36 (17)C9—C10—C5118.89 (18)
N2—C3—C4111.62 (17)C9—C10—C4119.31 (18)
N2—C3—H3A109.3C5—C10—C4121.77 (17)
C4—C3—H3A109.3N2—C11—H11A109.5
N2—C3—H3B109.3N2—C11—H11B109.5
C4—C3—H3B109.3H11A—C11—H11B109.5
H3A—C3—H3B108.0N2—C11—H11C109.5
C3—C4—C10110.52 (17)H11A—C11—H11C109.5
C3—C4—H4A109.5H11B—C11—H11C109.5
C10—C4—H4A109.5O2—C12—H12A109.5
C3—C4—H4B109.5O2—C12—H12B109.5
C10—C4—H4B109.5H12A—C12—H12B109.5
H4A—C4—H4B108.1O2—C12—H12C109.5
C6—C5—C10121.39 (18)H12A—C12—H12C109.5
C6—C5—H5A119.3H12B—C12—H12C109.5
C10—C5—H5A119.3O3—C13—H13A109.5
O2—C6—C5125.15 (18)O3—C13—H13B109.5
O2—C6—C7115.12 (17)H13A—C13—H13B109.5
C5—C6—C7119.72 (18)O3—C13—H13C109.5
O3—C7—C8126.13 (17)H13A—C13—H13C109.5
O3—C7—C6114.71 (17)H13B—C13—H13C109.5
C11—N2—C1—O14.7 (3)O3—C7—C8—C9178.96 (18)
C3—N2—C1—O1170.6 (2)C6—C7—C8—C90.8 (3)
C11—N2—C1—C9176.90 (19)C7—C8—C9—C100.1 (3)
C3—N2—C1—C911.0 (3)C7—C8—C9—C1177.46 (18)
C1—N2—C3—C442.8 (3)O1—C1—C9—C10166.03 (19)
C11—N2—C3—C4151.0 (2)N2—C1—C9—C1012.4 (3)
N2—C3—C4—C1049.5 (2)O1—C1—C9—C811.5 (3)
C12—O2—C6—C55.5 (3)N2—C1—C9—C8170.04 (17)
C12—O2—C6—C7174.07 (18)C8—C9—C10—C50.9 (3)
C10—C5—C6—O2179.79 (18)C1—C9—C10—C5176.65 (17)
C10—C5—C6—C70.3 (3)C8—C9—C10—C4179.05 (17)
C13—O3—C7—C87.9 (3)C1—C9—C10—C41.5 (3)
C13—O3—C7—C6171.89 (18)C6—C5—C10—C90.7 (3)
O2—C6—C7—O30.8 (3)C6—C5—C10—C4178.81 (18)
C5—C6—C7—O3178.79 (17)C3—C4—C10—C929.6 (3)
O2—C6—C7—C8179.40 (17)C3—C4—C10—C5152.30 (19)
C5—C6—C7—C81.0 (3)
 

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