organic compounds
The title compound, C11H13N2O5, was obtained during the preparation of 3,4-dihydro-6,7-dimethoxy-8-nitroisoquinoline from 3,4-dihydro-6,7-dimethoxyisoquinoline using NO2BF4 as a source of NO2+. 1H/13C NMR and X-ray analysis confirm the presence of a hydroxy group at position 1. The structure consists of layers of molecules parallel to the (12) plane.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601693X/bt2065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601693X/bt2065IIIasup2.hkl |
CCDC reference: 610705
Computing details top
Data collection: CAD-4-PC (Kretschmar, 1996); cell refinement: CAD-4-PC; data reduction: CFEO (Solans, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1998); molecular graphics: ORTEP-3.2 (Brueggemann & Schmid, 1990); software used to prepare material for publication: PLATON (Spek, 2003).
1-Hydroxy-6,7-dimethoxy-8-nitro-1,2,3,4-tetrahydroisoquinoline top
Crystal data top
C11H14N2O5 | Z = 2 |
Mr = 254.24 | F(000) = 268 |
Triclinic, P1 | Dx = 1.462 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.587 (7) Å | Cell parameters from 25 reflections |
b = 8.636 (5) Å | θ = 8–18° |
c = 8.746 (14) Å | µ = 0.12 mm−1 |
α = 80.04 (9)° | T = 293 K |
β = 64.67 (8)° | Prism, colourless |
γ = 85.18 (6)° | 0.4 × 0.2 × 0.2 mm |
V = 577.4 (11) Å3 |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.4° |
Graphite monochromator | h = −10→12 |
ω/2θ scans | k = −11→12 |
3356 measured reflections | l = 0→12 |
3356 independent reflections | 3 standard reflections every 120 min |
2298 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.040 | Hydrogen site location: mixed |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0292P)2 + 0.1026P] where P = (Fo2 + 2Fc2)/3 |
3356 reflections | (Δ/σ)max < 0.001 |
170 parameters | Δρmax = 0.23 e Å−3 |
3 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.4941 (2) | 0.28513 (18) | −0.00715 (17) | 0.0978 (5) | |
O2 | 0.37603 (17) | 0.06798 (18) | 0.13553 (15) | 0.0835 (4) | |
O3 | 0.22759 (11) | 0.38794 (12) | 0.64649 (12) | 0.0505 (2) | |
O4 | 0.19553 (11) | 0.32718 (12) | 0.36703 (12) | 0.0498 (2) | |
O5 | 0.85478 (15) | 0.19743 (13) | 0.00296 (13) | 0.0597 (3) | |
N1 | 0.44888 (14) | 0.18835 (16) | 0.11867 (14) | 0.0482 (3) | |
N2 | 0.88701 (13) | 0.00174 (13) | 0.20820 (13) | 0.0413 (2) | |
H2N | 0.8327 (15) | −0.0867 (9) | 0.2887 (14) | 0.050* | |
C1 | 0.47871 (15) | 0.21569 (14) | 0.26640 (15) | 0.0361 (3) | |
C2 | 0.63061 (14) | 0.16565 (14) | 0.28067 (15) | 0.0358 (3) | |
C3 | 0.64549 (15) | 0.19049 (14) | 0.42675 (15) | 0.0373 (3) | |
C4 | 0.51163 (15) | 0.26338 (15) | 0.55289 (15) | 0.0384 (3) | |
H4 | 0.5229 | 0.2776 | 0.6507 | 0.046* | |
C5 | 0.36255 (15) | 0.31454 (15) | 0.53348 (15) | 0.0376 (3) | |
C6 | 0.34426 (14) | 0.28961 (15) | 0.38693 (15) | 0.0375 (3) | |
C7 | 0.77265 (16) | 0.08480 (16) | 0.14437 (16) | 0.0428 (3) | |
H7 | 0.7195 | 0.0090 | 0.1103 | 0.051* | |
C8 | 0.94764 (17) | 0.0979 (2) | 0.29013 (19) | 0.0580 (4) | |
H8 | 0.9946 | 0.1944 | 0.2132 | 0.070* | |
H8A | 1.0392 | 0.0426 | 0.3151 | 0.070* | |
C9 | 0.80529 (16) | 0.13640 (18) | 0.45218 (17) | 0.0471 (3) | |
H9 | 0.8423 | 0.2185 | 0.4918 | 0.056* | |
H9A | 0.7791 | 0.0441 | 0.5394 | 0.056* | |
C10 | 0.1826 (2) | 0.4874 (2) | 0.2966 (2) | 0.0705 (5) | |
H10 | 0.2813 | 0.5130 | 0.1898 | 0.085* | |
H10A | 0.1780 | 0.5548 | 0.3749 | 0.085* | |
H10B | 0.0798 | 0.5019 | 0.2776 | 0.085* | |
C11 | 0.2369 (2) | 0.41194 (18) | 0.79995 (17) | 0.0534 (4) | |
H11 | 0.2311 | 0.3124 | 0.8707 | 0.064* | |
H11A | 0.1423 | 0.4777 | 0.8606 | 0.064* | |
H11B | 0.3436 | 0.4619 | 0.7716 | 0.064* | |
H5O | 0.937 (2) | 0.154 (2) | −0.069 (2) | 0.067 (5)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1473 (13) | 0.1080 (11) | 0.0671 (8) | −0.0123 (10) | −0.0786 (9) | 0.0090 (8) |
O2 | 0.0737 (8) | 0.1224 (11) | 0.0679 (8) | −0.0239 (8) | −0.0277 (6) | −0.0434 (8) |
O3 | 0.0393 (5) | 0.0701 (6) | 0.0483 (5) | 0.0175 (4) | −0.0217 (4) | −0.0241 (5) |
O4 | 0.0328 (4) | 0.0679 (6) | 0.0578 (6) | 0.0118 (4) | −0.0278 (4) | −0.0150 (5) |
O5 | 0.0583 (6) | 0.0655 (7) | 0.0437 (6) | 0.0202 (5) | −0.0151 (5) | −0.0066 (5) |
N1 | 0.0390 (6) | 0.0727 (8) | 0.0437 (6) | 0.0121 (5) | −0.0255 (5) | −0.0207 (6) |
N2 | 0.0395 (5) | 0.0442 (6) | 0.0432 (6) | 0.0174 (4) | −0.0219 (5) | −0.0106 (5) |
C1 | 0.0325 (6) | 0.0462 (7) | 0.0361 (6) | 0.0049 (5) | −0.0204 (5) | −0.0096 (5) |
C2 | 0.0315 (5) | 0.0435 (6) | 0.0369 (6) | 0.0068 (5) | −0.0185 (5) | −0.0098 (5) |
C3 | 0.0337 (6) | 0.0444 (7) | 0.0413 (6) | 0.0072 (5) | −0.0234 (5) | −0.0088 (5) |
C4 | 0.0353 (6) | 0.0490 (7) | 0.0377 (6) | 0.0058 (5) | −0.0209 (5) | −0.0117 (5) |
C5 | 0.0314 (6) | 0.0456 (7) | 0.0378 (6) | 0.0054 (5) | −0.0166 (5) | −0.0089 (5) |
C6 | 0.0299 (5) | 0.0466 (7) | 0.0419 (6) | 0.0057 (5) | −0.0209 (5) | −0.0090 (5) |
C7 | 0.0372 (6) | 0.0526 (7) | 0.0445 (7) | 0.0155 (5) | −0.0224 (5) | −0.0159 (6) |
C8 | 0.0388 (7) | 0.0877 (11) | 0.0593 (9) | 0.0186 (7) | −0.0308 (7) | −0.0226 (8) |
C9 | 0.0387 (6) | 0.0655 (9) | 0.0469 (7) | 0.0116 (6) | −0.0283 (6) | −0.0120 (6) |
C10 | 0.0585 (9) | 0.0732 (11) | 0.0861 (12) | 0.0190 (8) | −0.0434 (9) | −0.0026 (9) |
C11 | 0.0544 (8) | 0.0645 (9) | 0.0408 (7) | 0.0130 (7) | −0.0182 (6) | −0.0185 (7) |
Geometric parameters (Å, º) top
O1—N1 | 1.196 (2) | C3—C9 | 1.5061 (19) |
O2—N1 | 1.2129 (18) | C4—C5 | 1.3884 (19) |
O3—C5 | 1.355 (2) | C4—H4 | 0.9300 |
O3—C11 | 1.429 (3) | C5—C6 | 1.410 (3) |
O4—C6 | 1.3666 (17) | C7—H7 | 0.9800 |
O4—C10 | 1.430 (2) | C8—C9 | 1.492 (3) |
O5—C7 | 1.388 (3) | C8—H8 | 0.9700 |
O5—H5O | 0.835 (17) | C8—H8A | 0.9700 |
N1—C1 | 1.480 (3) | C9—H9 | 0.9700 |
N2—C7 | 1.4151 (19) | C9—H9A | 0.9700 |
N2—C8 | 1.439 (2) | C10—H10 | 0.9600 |
N2—H2N | 0.943 (7) | C10—H10A | 0.9600 |
C1—C6 | 1.385 (2) | C10—H10B | 0.9600 |
C1—C2 | 1.3891 (18) | C11—H11 | 0.9600 |
C2—C3 | 1.391 (3) | C11—H11A | 0.9600 |
C2—C7 | 1.516 (3) | C11—H11B | 0.9600 |
C3—C4 | 1.403 (2) | ||
C5—O3—C11 | 117.71 (13) | N2—C7—C2 | 111.12 (14) |
C6—O4—C10 | 114.66 (13) | O5—C7—H7 | 108.2 |
C7—O5—H5O | 107.9 (12) | N2—C7—H7 | 108.2 |
O1—N1—O2 | 124.10 (15) | C2—C7—H7 | 108.2 |
O1—N1—C1 | 119.21 (16) | N2—C8—C9 | 111.03 (15) |
O2—N1—C1 | 116.68 (15) | N2—C8—H8 | 109.4 |
C7—N2—C8 | 112.20 (12) | C9—C8—H8 | 109.4 |
C7—N2—H2N | 110.7 (6) | N2—C8—H8A | 109.4 |
C8—N2—H2N | 108.0 (6) | C9—C8—H8A | 109.4 |
C6—C1—C2 | 124.02 (13) | H8—C8—H8A | 108.0 |
C6—C1—N1 | 115.14 (13) | C8—C9—C3 | 111.32 (14) |
C2—C1—N1 | 120.82 (13) | C8—C9—H9 | 109.4 |
C1—C2—C3 | 117.14 (13) | C3—C9—H9 | 109.4 |
C1—C2—C7 | 121.40 (13) | C8—C9—H9A | 109.4 |
C3—C2—C7 | 121.45 (13) | C3—C9—H9A | 109.4 |
C2—C3—C4 | 120.69 (13) | H9—C9—H9A | 108.0 |
C2—C3—C9 | 119.97 (13) | O4—C10—H10 | 109.5 |
C4—C3—C9 | 119.33 (13) | O4—C10—H10A | 109.5 |
C5—C4—C3 | 120.79 (13) | H10—C10—H10A | 109.5 |
C5—C4—H4 | 119.6 | O4—C10—H10B | 109.5 |
C3—C4—H4 | 119.6 | H10—C10—H10B | 109.5 |
O3—C5—C4 | 125.21 (13) | H10A—C10—H10B | 109.5 |
O3—C5—C6 | 115.33 (13) | O3—C11—H11 | 109.5 |
C4—C5—C6 | 119.46 (13) | O3—C11—H11A | 109.5 |
O4—C6—C1 | 120.05 (13) | H11—C11—H11A | 109.5 |
O4—C6—C5 | 121.95 (13) | O3—C11—H11B | 109.5 |
C1—C6—C5 | 117.88 (13) | H11—C11—H11B | 109.5 |
O5—C7—N2 | 112.82 (14) | H11A—C11—H11B | 109.5 |
O5—C7—C2 | 108.22 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5O···N2i | 0.832 (17) | 2.056 (18) | 2.870 (5) | 166.2 (17) |
Symmetry code: (i) −x+2, −y, −z. |