Literature DB >> 21523004

6,9-Dimeth-oxy-3,4-dihydro-1H-1,4-oxazino[4,3-a]indol-1-one.

Cristian O Salas1, Ricardo A Tapia, Yolanda Prieto.   

Abstract

The title compound, C(13)H(13)NO(4), is one cyclization product of the reaction of ethyl 1-(2-bromo-eth-yl)-4,7-dimeth-oxy-1H-indole-2-carboxyl-ate with sodium azide in refluxing dioxane and was synthesized with the aim of finding new compounds with biological properties. Bond lengths and angles are within the expected values and confirm the bond orders giving in the scheme. The shortest contacts between mol-ecules are set along the a axis, where stacked mol-ecules related by an inversion center form an ABAB array through π-π stacking inter-actions with centroid-centroid distances ranging from 3.922 (2) to 4.396 (2) Å. Weak C-H⋯O hydrogen bonds further stabilize the structure.

Entities:  

Year:  2011        PMID： 21523004      PMCID： PMC3051655          DOI： 10.1107/S1600536811000249

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to oxazinoindoles as inter­mediates in the chemistry of bioactive compounds, see: Demerson et al. (1975 ▶); Fedouloff et al. (2001 ▶); Shchekotikhin et al. (2004 ▶). Several synthetic strategies for the preparation of oxazinoindoles have been reported, for some examples, see: Abbiati et al. (2005 ▶); Brudeli et al. (2010 ▶); Fu et al. (2010 ▶).

Experimental

Crystal data

C13H13NO4 M = 247.24 Monoclinic, a = 8.414 (2) Å b = 6.9722 (19) Å c = 19.331 (5) Å β = 101.276 (4)° V = 1112.1 (5) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 100 K 0.72 × 0.27 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.925, T max = 0.972 10088 measured reflections 2277 independent reflections 1922 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.102 S = 1.06 2277 reflections 165 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000249/sj5085sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000249/sj5085Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H13NO4Dx = 1.477 Mg m−3
Mr = 247.24Melting point = 419.0–419.5 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.414 (2) ÅCell parameters from 1832 reflections
b = 6.9722 (19) Åθ = 2.5–27.5°
c = 19.331 (5) ŵ = 0.11 mm−1
β = 101.276 (4)°T = 100 K
V = 1112.1 (5) Å3Prism, colourless
Z = 40.72 × 0.27 × 0.26 mm
F(000) = 520
Bruker APEXII CCD diffractometer2277 independent reflections
Radiation source: fine-focus sealed tube1922 reflections with I > 2σ(I)
graphiteRint = 0.030
φ and ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −10→10
Tmin = 0.925, Tmax = 0.972k = 0→8
10088 measured reflectionsl = 0→24
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0537P)2 + 0.3721P] where P = (Fo2 + 2Fc2)/3
2277 reflections(Δ/σ)max = 0.001
165 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Experimental. 6,9-Dimethoxy-3,4-dihydro-1H-[1,4]oxazino[4,3-a]indol-1-one (2) IR (NaCl, cm-1): 1730 (CO). 1H RMN (CDCl3, 200 MHz) d 3.89 (s, 6H, 3xOCH3); 4.63–4.76 (m, 4H, 2xCH2); 6.34 (d, 1H, J =8.3 Hz, H-6); 6.61 (d, 1H, J =8.3 Hz, H7); 7.50 (s, 1H, H9). 13C RMN (CDCl3, 50 MHz) d 42.8 (CH2); 55.6 (OCH3); 55.7 (OCH3); 66.9 (CH2); 99.1 (C9); 105.5 (C6); 108.5 (C7); 120.3 (C8a); 123.0 (C9a); 128.1 (C5a); 142.1 (C5); 148.7 (C8); 159.7 (CO). MS (CI) m/z 248.1 [(M+1)+, 100].
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
N10.79680 (13)0.12018 (17)0.99864 (6)0.0178 (3)
C20.86881 (15)0.3060 (2)1.02003 (7)0.0199 (3)
H2A0.86310.39070.97850.024*
H2B0.98390.29081.04320.024*
C30.77300 (16)0.3898 (2)1.07063 (7)0.0212 (3)
H3A0.81960.51571.08740.025*
H3B0.65980.41101.04580.025*
O40.77361 (12)0.26469 (14)1.13077 (5)0.0230 (2)
O50.69846 (12)−0.01995 (15)1.16341 (5)0.0258 (3)
C50.72921 (15)0.0798 (2)1.11666 (7)0.0197 (3)
C60.72754 (15)0.0118 (2)1.04487 (7)0.0183 (3)
C70.66807 (15)−0.1555 (2)1.01289 (7)0.0182 (3)
H70.6138−0.25421.03300.022*
C80.70291 (15)−0.1534 (2)0.94399 (7)0.0179 (3)
C90.67102 (15)−0.2832 (2)0.88665 (7)0.0192 (3)
C100.72240 (16)−0.2367 (2)0.82573 (7)0.0221 (3)
H100.7025−0.32270.78690.026*
C110.80488 (16)−0.0619 (2)0.81999 (8)0.0225 (3)
H110.8394−0.03400.77710.027*
C120.83662 (15)0.0683 (2)0.87398 (7)0.0195 (3)
C130.78441 (15)0.0205 (2)0.93686 (7)0.0176 (3)
O140.59004 (11)−0.44721 (14)0.89811 (5)0.0225 (2)
C150.52860 (17)−0.5606 (2)0.83664 (8)0.0259 (3)
H15A0.4598−0.48060.80120.039*
H15B0.4647−0.66750.84960.039*
H15C0.6194−0.61090.81720.039*
O160.91115 (11)0.24306 (15)0.87236 (5)0.0228 (3)
C170.94995 (18)0.2967 (2)0.80615 (7)0.0256 (3)
H17A1.03700.21420.79610.038*
H17B0.98560.43070.80830.038*
H17C0.85380.28190.76870.038*
U11U22U33U12U13U23
N10.0153 (5)0.0198 (6)0.0184 (6)−0.0006 (4)0.0035 (4)0.0009 (4)
C20.0163 (6)0.0198 (7)0.0227 (7)−0.0024 (5)0.0019 (5)0.0000 (6)
C30.0218 (7)0.0199 (7)0.0212 (7)0.0007 (5)0.0023 (5)0.0006 (6)
O40.0275 (5)0.0220 (5)0.0192 (5)−0.0008 (4)0.0039 (4)−0.0007 (4)
O50.0297 (5)0.0293 (6)0.0185 (5)−0.0027 (4)0.0049 (4)0.0024 (4)
C50.0145 (6)0.0228 (7)0.0208 (7)0.0019 (5)0.0010 (5)0.0003 (6)
C60.0143 (6)0.0220 (7)0.0185 (7)0.0032 (5)0.0031 (5)0.0034 (5)
C70.0137 (6)0.0200 (7)0.0204 (7)0.0020 (5)0.0023 (5)0.0024 (5)
C80.0115 (6)0.0215 (7)0.0201 (7)0.0035 (5)0.0013 (5)0.0014 (5)
C90.0127 (6)0.0209 (7)0.0235 (7)0.0018 (5)0.0020 (5)−0.0010 (6)
C100.0175 (7)0.0271 (8)0.0214 (7)0.0021 (6)0.0032 (5)−0.0051 (6)
C110.0180 (6)0.0299 (8)0.0206 (7)0.0029 (6)0.0062 (5)0.0010 (6)
C120.0134 (6)0.0241 (7)0.0213 (7)0.0013 (5)0.0040 (5)0.0024 (6)
C130.0127 (6)0.0214 (7)0.0180 (7)0.0028 (5)0.0013 (5)0.0002 (5)
O140.0210 (5)0.0230 (5)0.0232 (5)−0.0037 (4)0.0040 (4)−0.0039 (4)
C150.0229 (7)0.0273 (8)0.0273 (8)−0.0038 (6)0.0044 (6)−0.0083 (6)
O160.0222 (5)0.0270 (6)0.0200 (5)−0.0043 (4)0.0063 (4)0.0019 (4)
C170.0237 (7)0.0331 (9)0.0212 (7)−0.0012 (6)0.0076 (6)0.0053 (6)
N1—C131.3678 (17)C9—C101.370 (2)
N1—C61.3830 (17)C9—O141.3712 (17)
N1—C21.4557 (18)C10—C111.418 (2)
C2—C31.5019 (19)C10—H100.9500
C2—H2A0.9900C11—C121.369 (2)
C2—H2B0.9900C11—H110.9500
C3—O41.4525 (17)C12—O161.3736 (18)
C3—H3A0.9900C12—C131.4108 (19)
C3—H3B0.9900O14—C151.4365 (17)
O4—C51.3552 (18)C15—H15A0.9800
O5—C51.2077 (17)C15—H15B0.9800
C5—C61.4638 (19)C15—H15C0.9800
C6—C71.368 (2)O16—C171.4310 (17)
C7—C81.4188 (19)C17—H17A0.9800
C7—H70.9500C17—H17B0.9800
C8—C131.413 (2)C17—H17C0.9800
C8—C91.4156 (19)
C13—N1—C6108.48 (12)C10—C9—C8118.59 (13)
C13—N1—C2131.04 (12)O14—C9—C8115.52 (12)
C6—N1—C2120.48 (12)C9—C10—C11120.80 (13)
N1—C2—C3106.52 (11)C9—C10—H10119.6
N1—C2—H2A110.4C11—C10—H10119.6
C3—C2—H2A110.4C12—C11—C10122.39 (13)
N1—C2—H2B110.4C12—C11—H11118.8
C3—C2—H2B110.4C10—C11—H11118.8
H2A—C2—H2B108.6C11—C12—O16126.33 (13)
O4—C3—C2111.70 (11)C11—C12—C13116.95 (13)
O4—C3—H3A109.3O16—C12—C13116.70 (12)
C2—C3—H3A109.3N1—C13—C12130.47 (13)
O4—C3—H3B109.3N1—C13—C8107.84 (12)
C2—C3—H3B109.3C12—C13—C8121.69 (12)
H3A—C3—H3B107.9C9—O14—C15115.79 (11)
C5—O4—C3116.89 (11)O14—C15—H15A109.5
O5—C5—O4119.21 (13)O14—C15—H15B109.5
O5—C5—C6124.02 (14)H15A—C15—H15B109.5
O4—C5—C6116.73 (12)O14—C15—H15C109.5
C7—C6—N1109.68 (12)H15A—C15—H15C109.5
C7—C6—C5129.72 (13)H15B—C15—H15C109.5
N1—C6—C5120.58 (13)C12—O16—C17115.93 (11)
C6—C7—C8106.91 (12)O16—C17—H17A109.5
C6—C7—H7126.5O16—C17—H17B109.5
C8—C7—H7126.5H17A—C17—H17B109.5
C13—C8—C9119.58 (13)O16—C17—H17C109.5
C13—C8—C7107.08 (12)H17A—C17—H17C109.5
C9—C8—C7133.33 (13)H17B—C17—H17C109.5
C10—C9—O14125.89 (13)
C13—N1—C2—C3149.07 (13)O14—C9—C10—C11179.79 (12)
C6—N1—C2—C3−32.03 (15)C8—C9—C10—C11−0.4 (2)
N1—C2—C3—O457.70 (13)C9—C10—C11—C12−0.3 (2)
C2—C3—O4—C5−52.35 (15)C10—C11—C12—O16−177.91 (12)
C3—O4—C5—O5−166.24 (12)C10—C11—C12—C130.5 (2)
C3—O4—C5—C615.92 (16)C6—N1—C13—C12−179.71 (13)
C13—N1—C6—C7−1.05 (15)C2—N1—C13—C12−0.7 (2)
C2—N1—C6—C7179.83 (11)C6—N1—C13—C81.00 (14)
C13—N1—C6—C5177.50 (11)C2—N1—C13—C8180.00 (12)
C2—N1—C6—C5−1.62 (18)C11—C12—C13—N1−179.28 (13)
O5—C5—C6—C712.2 (2)O16—C12—C13—N1−0.7 (2)
O4—C5—C6—C7−170.05 (13)C11—C12—C13—C8−0.07 (19)
O5—C5—C6—N1−166.01 (12)O16—C12—C13—C8178.48 (11)
O4—C5—C6—N111.72 (18)C9—C8—C13—N1178.81 (11)
N1—C6—C7—C80.66 (14)C7—C8—C13—N1−0.59 (14)
C5—C6—C7—C8−177.72 (12)C9—C8—C13—C12−0.56 (19)
C6—C7—C8—C13−0.04 (14)C7—C8—C13—C12−179.96 (12)
C6—C7—C8—C9−179.33 (13)C10—C9—O14—C15−12.25 (19)
C13—C8—C9—C100.77 (18)C8—C9—O14—C15167.92 (12)
C7—C8—C9—C10179.98 (13)C11—C12—O16—C173.90 (19)
C13—C8—C9—O14−179.38 (11)C13—C12—O16—C17−174.50 (11)
C7—C8—C9—O14−0.2 (2)
D—H···AD—HH···AD···AD—H···A
C2—H2a···O160.992.402.9776 (18)117
C3—H3B···O14i0.992.563.2524 (19)127 (4)
C15—H15B···O5ii0.982.563.493 (2)159 (4)
C17—H17A···O5iii0.982.593.484 (2)151 (4)
CgI-CgJ*CgI-CgJ(Å)**Alpha(°)***Beta(°)****CgI_Perp(Å)*****
Cg(1)-Cg(1)4.1164 (14)(a)034.50-3.3925 (6)
Cg(1)-Cg(1)4.3962 (14)(b)035.723.5692 (6)
Cg(1)-Cg(3)4.6434 (15)(b)0.50 (7)40.183.5476 (6)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2a⋯O160.992.402.9776 (18)117
C3—H3B⋯O14i0.992.563.2524 (19)127 (4)
C15—H15B⋯O5ii0.982.563.493 (2)159 (4)
C17—H17A⋯O5iii0.982.593.484 (2)151 (4)

Symmetry codes: (i) ; (ii) ; (iii) .

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