1-Hydr­oxy-6,7-dimeth­oxy-8-nitro-1,2,3,4-tetra­hydro­isoquinoline

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.

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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: mixed
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0292P)^2 + 0.1026P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···N2^i	0.832 (17)	2.056 (18)	2.870 (5)	166.2 (17)

Symmetry code: (i) −x+2, −y, −z.