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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\overline{1}) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601693X/bt2065sup1.cif
Contains datablocks IIIa, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601693X/bt2065IIIasup2.hkl
Contains datablock IIIa

CCDC reference: 610705

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.097
  • Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found




Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C8 .. 8.41 su PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O2 .. 2.79 Ang.
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2N ... ?
0 ALERT level A = In general: serious problem 2 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 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion

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
C11H14N2O5Z = 2
Mr = 254.24F(000) = 268
Triclinic, P1Dx = 1.462 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.587 (7) ÅCell parameters from 25 reflections
b = 8.636 (5) Åθ = 8–18°
c = 8.746 (14) ŵ = 0.12 mm1
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 tubeθmax = 30.0°, θmin = 2.4°
Graphite monochromatorh = 1012
ω/2θ scansk = 1112
3356 measured reflectionsl = 012
3356 independent reflections3 standard reflections every 120 min
2298 reflections with I > 2σ(I) intensity decay: none
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)] = 0.040Hydrogen site location: mixed
wR(F2) = 0.097H 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 parametersΔρmax = 0.23 e Å3
3 restraintsΔρmin = 0.18 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4941 (2)0.28513 (18)0.00715 (17)0.0978 (5)
O20.37603 (17)0.06798 (18)0.13553 (15)0.0835 (4)
O30.22759 (11)0.38794 (12)0.64649 (12)0.0505 (2)
O40.19553 (11)0.32718 (12)0.36703 (12)0.0498 (2)
O50.85478 (15)0.19743 (13)0.00296 (13)0.0597 (3)
N10.44888 (14)0.18835 (16)0.11867 (14)0.0482 (3)
N20.88701 (13)0.00174 (13)0.20820 (13)0.0413 (2)
H2N0.8327 (15)0.0867 (9)0.2887 (14)0.050*
C10.47871 (15)0.21569 (14)0.26640 (15)0.0361 (3)
C20.63061 (14)0.16565 (14)0.28067 (15)0.0358 (3)
C30.64549 (15)0.19049 (14)0.42675 (15)0.0373 (3)
C40.51163 (15)0.26338 (15)0.55289 (15)0.0384 (3)
H40.52290.27760.65070.046*
C50.36255 (15)0.31454 (15)0.53348 (15)0.0376 (3)
C60.34426 (14)0.28961 (15)0.38693 (15)0.0375 (3)
C70.77265 (16)0.08480 (16)0.14437 (16)0.0428 (3)
H70.71950.00900.11030.051*
C80.94764 (17)0.0979 (2)0.29013 (19)0.0580 (4)
H80.99460.19440.21320.070*
H8A1.03920.04260.31510.070*
C90.80529 (16)0.13640 (18)0.45218 (17)0.0471 (3)
H90.84230.21850.49180.056*
H9A0.77910.04410.53940.056*
C100.1826 (2)0.4874 (2)0.2966 (2)0.0705 (5)
H100.28130.51300.18980.085*
H10A0.17800.55480.37490.085*
H10B0.07980.50190.27760.085*
C110.2369 (2)0.41194 (18)0.79995 (17)0.0534 (4)
H110.23110.31240.87070.064*
H11A0.14230.47770.86060.064*
H11B0.34360.46190.77160.064*
H5O0.937 (2)0.154 (2)0.069 (2)0.067 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1473 (13)0.1080 (11)0.0671 (8)0.0123 (10)0.0786 (9)0.0090 (8)
O20.0737 (8)0.1224 (11)0.0679 (8)0.0239 (8)0.0277 (6)0.0434 (8)
O30.0393 (5)0.0701 (6)0.0483 (5)0.0175 (4)0.0217 (4)0.0241 (5)
O40.0328 (4)0.0679 (6)0.0578 (6)0.0118 (4)0.0278 (4)0.0150 (5)
O50.0583 (6)0.0655 (7)0.0437 (6)0.0202 (5)0.0151 (5)0.0066 (5)
N10.0390 (6)0.0727 (8)0.0437 (6)0.0121 (5)0.0255 (5)0.0207 (6)
N20.0395 (5)0.0442 (6)0.0432 (6)0.0174 (4)0.0219 (5)0.0106 (5)
C10.0325 (6)0.0462 (7)0.0361 (6)0.0049 (5)0.0204 (5)0.0096 (5)
C20.0315 (5)0.0435 (6)0.0369 (6)0.0068 (5)0.0185 (5)0.0098 (5)
C30.0337 (6)0.0444 (7)0.0413 (6)0.0072 (5)0.0234 (5)0.0088 (5)
C40.0353 (6)0.0490 (7)0.0377 (6)0.0058 (5)0.0209 (5)0.0117 (5)
C50.0314 (6)0.0456 (7)0.0378 (6)0.0054 (5)0.0166 (5)0.0089 (5)
C60.0299 (5)0.0466 (7)0.0419 (6)0.0057 (5)0.0209 (5)0.0090 (5)
C70.0372 (6)0.0526 (7)0.0445 (7)0.0155 (5)0.0224 (5)0.0159 (6)
C80.0388 (7)0.0877 (11)0.0593 (9)0.0186 (7)0.0308 (7)0.0226 (8)
C90.0387 (6)0.0655 (9)0.0469 (7)0.0116 (6)0.0283 (6)0.0120 (6)
C100.0585 (9)0.0732 (11)0.0861 (12)0.0190 (8)0.0434 (9)0.0026 (9)
C110.0544 (8)0.0645 (9)0.0408 (7)0.0130 (7)0.0182 (6)0.0185 (7)
Geometric parameters (Å, º) top
O1—N11.196 (2)C3—C91.5061 (19)
O2—N11.2129 (18)C4—C51.3884 (19)
O3—C51.355 (2)C4—H40.9300
O3—C111.429 (3)C5—C61.410 (3)
O4—C61.3666 (17)C7—H70.9800
O4—C101.430 (2)C8—C91.492 (3)
O5—C71.388 (3)C8—H80.9700
O5—H5O0.835 (17)C8—H8A0.9700
N1—C11.480 (3)C9—H90.9700
N2—C71.4151 (19)C9—H9A0.9700
N2—C81.439 (2)C10—H100.9600
N2—H2N0.943 (7)C10—H10A0.9600
C1—C61.385 (2)C10—H10B0.9600
C1—C21.3891 (18)C11—H110.9600
C2—C31.391 (3)C11—H11A0.9600
C2—C71.516 (3)C11—H11B0.9600
C3—C41.403 (2)
C5—O3—C11117.71 (13)N2—C7—C2111.12 (14)
C6—O4—C10114.66 (13)O5—C7—H7108.2
C7—O5—H5O107.9 (12)N2—C7—H7108.2
O1—N1—O2124.10 (15)C2—C7—H7108.2
O1—N1—C1119.21 (16)N2—C8—C9111.03 (15)
O2—N1—C1116.68 (15)N2—C8—H8109.4
C7—N2—C8112.20 (12)C9—C8—H8109.4
C7—N2—H2N110.7 (6)N2—C8—H8A109.4
C8—N2—H2N108.0 (6)C9—C8—H8A109.4
C6—C1—C2124.02 (13)H8—C8—H8A108.0
C6—C1—N1115.14 (13)C8—C9—C3111.32 (14)
C2—C1—N1120.82 (13)C8—C9—H9109.4
C1—C2—C3117.14 (13)C3—C9—H9109.4
C1—C2—C7121.40 (13)C8—C9—H9A109.4
C3—C2—C7121.45 (13)C3—C9—H9A109.4
C2—C3—C4120.69 (13)H9—C9—H9A108.0
C2—C3—C9119.97 (13)O4—C10—H10109.5
C4—C3—C9119.33 (13)O4—C10—H10A109.5
C5—C4—C3120.79 (13)H10—C10—H10A109.5
C5—C4—H4119.6O4—C10—H10B109.5
C3—C4—H4119.6H10—C10—H10B109.5
O3—C5—C4125.21 (13)H10A—C10—H10B109.5
O3—C5—C6115.33 (13)O3—C11—H11109.5
C4—C5—C6119.46 (13)O3—C11—H11A109.5
O4—C6—C1120.05 (13)H11—C11—H11A109.5
O4—C6—C5121.95 (13)O3—C11—H11B109.5
C1—C6—C5117.88 (13)H11—C11—H11B109.5
O5—C7—N2112.82 (14)H11A—C11—H11B109.5
O5—C7—C2108.22 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···N2i0.832 (17)2.056 (18)2.870 (5)166.2 (17)
Symmetry code: (i) x+2, y, z.
 

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