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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
CCDC reference: 270283
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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(2
H)-one
top
Crystal data top
C12H15NO3 | F(000) = 472 |
Mr = 221.25 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7846 (17) Å | Cell parameters from 912 reflections |
b = 16.865 (3) Å | θ = 2.1–26.5° |
c = 6.8914 (12) Å | µ = 0.10 mm−1 |
β = 103.934 (3)° | T = 273 K |
V = 1103.7 (3) Å3 | Plate, colourless |
Z = 4 | 0.31 × 0.11 × 0.06 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2285 independent reflections |
Radiation source: fine-focus sealed tube | 1673 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 2.1° |
ω scans | h = −10→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −21→20 |
Tmin = 0.971, Tmax = 0.994 | l = −6→8 |
6118 measured reflections | |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.56580 (17) | −0.08915 (10) | 0.2136 (2) | 0.0672 (5) | |
O2 | 1.01861 (15) | 0.17575 (8) | 0.5321 (2) | 0.0620 (4) | |
O3 | 0.85128 (16) | 0.16425 (9) | 0.1858 (2) | 0.0649 (5) | |
N2 | 0.60556 (18) | −0.11541 (10) | 0.5436 (3) | 0.0571 (5) | |
C1 | 0.6259 (2) | −0.07281 (12) | 0.3866 (3) | 0.0504 (5) | |
C3 | 0.6599 (2) | −0.08909 (14) | 0.7492 (3) | 0.0615 (6) | |
H3A | 0.6588 | −0.1332 | 0.8392 | 0.074* | |
H3B | 0.5992 | −0.0479 | 0.7799 | 0.074* | |
C4 | 0.8069 (2) | −0.05778 (13) | 0.7825 (3) | 0.0570 (5) | |
H4A | 0.8713 | −0.1013 | 0.7806 | 0.068* | |
H4B | 0.8340 | −0.0326 | 0.9127 | 0.068* | |
C5 | 0.9155 (2) | 0.06187 (12) | 0.6580 (3) | 0.0494 (5) | |
H5A | 0.9762 | 0.0669 | 0.7840 | 0.059* | |
C6 | 0.9255 (2) | 0.11468 (11) | 0.5105 (3) | 0.0478 (5) | |
C7 | 0.8338 (2) | 0.10780 (12) | 0.3194 (3) | 0.0478 (5) | |
C8 | 0.73702 (19) | 0.04734 (11) | 0.2833 (3) | 0.0461 (5) | |
H8A | 0.6769 | 0.0420 | 0.1571 | 0.055* | |
C9 | 0.7280 (2) | −0.00628 (11) | 0.4345 (3) | 0.0452 (5) | |
C10 | 0.8168 (2) | 0.00121 (11) | 0.6231 (3) | 0.0460 (5) | |
C11 | 0.5020 (3) | −0.17871 (14) | 0.5088 (4) | 0.0732 (7) | |
H11A | 0.4747 | −0.1905 | 0.3685 | 0.110* | |
H11B | 0.4208 | −0.1623 | 0.5537 | 0.110* | |
H11C | 0.5420 | −0.2252 | 0.5812 | 0.110* | |
C12 | 1.1050 (2) | 0.19050 (14) | 0.7269 (3) | 0.0670 (6) | |
H12A | 1.1656 | 0.2348 | 0.7219 | 0.100* | |
H12B | 1.1612 | 0.1445 | 0.7731 | 0.100* | |
H12C | 1.0466 | 0.2021 | 0.8169 | 0.100* | |
C13 | 0.7513 (2) | 0.16698 (14) | 0.0011 (3) | 0.0614 (6) | |
H13A | 0.7750 | 0.2089 | −0.0792 | 0.092* | |
H13B | 0.6596 | 0.1766 | 0.0235 | 0.092* | |
H13C | 0.7510 | 0.1173 | −0.0670 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0702 (10) | 0.0759 (11) | 0.0495 (9) | −0.0194 (8) | 0.0025 (7) | −0.0059 (7) |
O2 | 0.0592 (9) | 0.0580 (9) | 0.0606 (9) | −0.0125 (7) | −0.0017 (7) | 0.0025 (7) |
O3 | 0.0604 (9) | 0.0709 (10) | 0.0561 (9) | −0.0139 (8) | −0.0003 (7) | 0.0159 (7) |
N2 | 0.0579 (11) | 0.0601 (11) | 0.0534 (11) | −0.0112 (9) | 0.0137 (8) | 0.0005 (8) |
C1 | 0.0462 (11) | 0.0550 (12) | 0.0489 (12) | −0.0007 (9) | 0.0092 (9) | −0.0043 (9) |
C3 | 0.0645 (14) | 0.0710 (15) | 0.0487 (12) | −0.0042 (11) | 0.0134 (10) | 0.0067 (10) |
C4 | 0.0594 (13) | 0.0606 (13) | 0.0486 (12) | 0.0006 (10) | 0.0081 (10) | 0.0049 (10) |
C5 | 0.0470 (11) | 0.0550 (12) | 0.0414 (10) | 0.0044 (9) | 0.0011 (8) | −0.0021 (9) |
C6 | 0.0423 (10) | 0.0466 (11) | 0.0515 (11) | −0.0001 (8) | 0.0055 (9) | −0.0048 (9) |
C7 | 0.0444 (11) | 0.0525 (12) | 0.0453 (11) | 0.0035 (9) | 0.0084 (8) | 0.0041 (9) |
C8 | 0.0418 (10) | 0.0540 (12) | 0.0395 (10) | 0.0021 (9) | 0.0041 (8) | −0.0023 (8) |
C9 | 0.0435 (10) | 0.0479 (11) | 0.0446 (10) | 0.0029 (8) | 0.0112 (8) | −0.0033 (8) |
C10 | 0.0440 (10) | 0.0484 (11) | 0.0445 (11) | 0.0046 (8) | 0.0085 (9) | −0.0006 (8) |
C11 | 0.0754 (16) | 0.0715 (16) | 0.0732 (16) | −0.0216 (13) | 0.0190 (13) | −0.0015 (12) |
C12 | 0.0572 (13) | 0.0631 (14) | 0.0702 (15) | −0.0094 (11) | −0.0048 (11) | −0.0120 (11) |
C13 | 0.0659 (14) | 0.0655 (14) | 0.0480 (12) | 0.0046 (11) | 0.0044 (10) | 0.0092 (10) |
Geometric parameters (Å, º) top
O1—C1 | 1.227 (2) | C5—C10 | 1.388 (3) |
O2—C6 | 1.359 (2) | C5—H5A | 0.9300 |
O2—C12 | 1.426 (2) | C6—C7 | 1.409 (3) |
O3—C7 | 1.364 (2) | C7—C8 | 1.373 (3) |
O3—C13 | 1.407 (2) | C8—C9 | 1.398 (3) |
N2—C1 | 1.353 (3) | C8—H8A | 0.9300 |
N2—C11 | 1.451 (3) | C9—C10 | 1.385 (3) |
N2—C3 | 1.458 (3) | C11—H11A | 0.9600 |
C1—C9 | 1.486 (3) | C11—H11B | 0.9600 |
C3—C4 | 1.497 (3) | C11—H11C | 0.9600 |
C3—H3A | 0.9700 | C12—H12A | 0.9600 |
C3—H3B | 0.9700 | C12—H12B | 0.9600 |
C4—C10 | 1.502 (3) | C12—H12C | 0.9600 |
C4—H4A | 0.9700 | C13—H13A | 0.9600 |
C4—H4B | 0.9700 | C13—H13B | 0.9600 |
C5—C6 | 1.373 (3) | C13—H13C | 0.9600 |
| | | |
C6—O2—C12 | 117.75 (16) | C8—C7—C6 | 119.15 (17) |
C7—O3—C13 | 117.41 (16) | C7—C8—C9 | 120.68 (17) |
C1—N2—C11 | 119.30 (18) | C7—C8—H8A | 119.7 |
C1—N2—C3 | 121.76 (17) | C9—C8—H8A | 119.7 |
C11—N2—C3 | 117.48 (17) | C10—C9—C8 | 120.16 (18) |
O1—C1—N2 | 121.99 (19) | C10—C9—C1 | 120.92 (17) |
O1—C1—C9 | 121.63 (18) | C8—C9—C1 | 118.88 (17) |
N2—C1—C9 | 116.36 (17) | C9—C10—C5 | 118.89 (18) |
N2—C3—C4 | 111.62 (17) | C9—C10—C4 | 119.31 (18) |
N2—C3—H3A | 109.3 | C5—C10—C4 | 121.77 (17) |
C4—C3—H3A | 109.3 | N2—C11—H11A | 109.5 |
N2—C3—H3B | 109.3 | N2—C11—H11B | 109.5 |
C4—C3—H3B | 109.3 | H11A—C11—H11B | 109.5 |
H3A—C3—H3B | 108.0 | N2—C11—H11C | 109.5 |
C3—C4—C10 | 110.52 (17) | H11A—C11—H11C | 109.5 |
C3—C4—H4A | 109.5 | H11B—C11—H11C | 109.5 |
C10—C4—H4A | 109.5 | O2—C12—H12A | 109.5 |
C3—C4—H4B | 109.5 | O2—C12—H12B | 109.5 |
C10—C4—H4B | 109.5 | H12A—C12—H12B | 109.5 |
H4A—C4—H4B | 108.1 | O2—C12—H12C | 109.5 |
C6—C5—C10 | 121.39 (18) | H12A—C12—H12C | 109.5 |
C6—C5—H5A | 119.3 | H12B—C12—H12C | 109.5 |
C10—C5—H5A | 119.3 | O3—C13—H13A | 109.5 |
O2—C6—C5 | 125.15 (18) | O3—C13—H13B | 109.5 |
O2—C6—C7 | 115.12 (17) | H13A—C13—H13B | 109.5 |
C5—C6—C7 | 119.72 (18) | O3—C13—H13C | 109.5 |
O3—C7—C8 | 126.13 (17) | H13A—C13—H13C | 109.5 |
O3—C7—C6 | 114.71 (17) | H13B—C13—H13C | 109.5 |
| | | |
C11—N2—C1—O1 | −4.7 (3) | O3—C7—C8—C9 | −178.96 (18) |
C3—N2—C1—O1 | −170.6 (2) | C6—C7—C8—C9 | 0.8 (3) |
C11—N2—C1—C9 | 176.90 (19) | C7—C8—C9—C10 | 0.1 (3) |
C3—N2—C1—C9 | 11.0 (3) | C7—C8—C9—C1 | −177.46 (18) |
C1—N2—C3—C4 | −42.8 (3) | O1—C1—C9—C10 | −166.03 (19) |
C11—N2—C3—C4 | 151.0 (2) | N2—C1—C9—C10 | 12.4 (3) |
N2—C3—C4—C10 | 49.5 (2) | O1—C1—C9—C8 | 11.5 (3) |
C12—O2—C6—C5 | −5.5 (3) | N2—C1—C9—C8 | −170.04 (17) |
C12—O2—C6—C7 | 174.07 (18) | C8—C9—C10—C5 | −0.9 (3) |
C10—C5—C6—O2 | 179.79 (18) | C1—C9—C10—C5 | 176.65 (17) |
C10—C5—C6—C7 | 0.3 (3) | C8—C9—C10—C4 | −179.05 (17) |
C13—O3—C7—C8 | 7.9 (3) | C1—C9—C10—C4 | −1.5 (3) |
C13—O3—C7—C6 | −171.89 (18) | C6—C5—C10—C9 | 0.7 (3) |
O2—C6—C7—O3 | −0.8 (3) | C6—C5—C10—C4 | 178.81 (18) |
C5—C6—C7—O3 | 178.79 (17) | C3—C4—C10—C9 | −29.6 (3) |
O2—C6—C7—C8 | 179.40 (17) | C3—C4—C10—C5 | 152.30 (19) |
C5—C6—C7—C8 | −1.0 (3) | | |
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