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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o913.
Published online 2008 April 26. doi:  10.1107/S1600536808011185
PMCID: PMC2961249

2-[2-(1H-indol-3-yl)ethyl­iminiomethyl]-4-nitro­phenolate

Abstract

The title Schiff base, C17H15N3O3, exists in the zwitterionic form with the phenol H atom transferred to the imine group. Adjacent zwitterions are linked into a linear chain running along the a axis by an indole–hydr­oxy N—H(...)O hydrogen bond [3.100 (2) Å].

Related literature

For the structure of the zwitterionic 2-{[3-(indol-3-yl)propen­yl]methyl­ammonio}-4-methyl­phenolate, see: Ali et al. (2007 [triangle]).

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Object name is e-64-0o913-scheme1.jpg

Experimental

Crystal data

  • C17H15N3O3
  • M r = 309.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o913-efi1.jpg
  • a = 14.5990 (7) Å
  • b = 9.5027 (5) Å
  • c = 21.5373 (10) Å
  • β = 95.712 (2)°
  • V = 2973.0 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 139 (2) K
  • 0.51 × 0.30 × 0.19 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 6383 measured reflections
  • 3312 independent reflections
  • 2403 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.161
  • S = 1.06
  • 3312 reflections
  • 216 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.18 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011185/bv2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011185/bv2090Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02-03–2031) and the Fundamental Research Grant Scheme (FP064/2006 A) for supporting this study.

supplementary crystallographic information

Experimental

Tryptamine (0.32 g, 2 mmol) and 5-nitrosalisylaldehyde (0.33 g, 21.9 mmol) were refluxed in ethanol (50 ml) for 2 h. The solvent was removed to give the product Schiff base, and crystals were obtained by recrystallization from THF.

Refinement

The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2Ueq(C). The amino hydrogen atom was located in a difference Fouier map, and was refined with a distance restraint of N–H 0.88±0.01 Å.

The final difference Fourier map had a large peak at 1.5 Å from O1 and H2n. This peak is not near the the nitro group even though this group has larger thermal parameters than the rest of the molecule.

Figures

Fig. 1.
Thermal ellipsoid plot of C17H15N3O3. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii.

Crystal data

C17H15N3O3F(000) = 1296
Mr = 309.32Dx = 1.382 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -c 2ycCell parameters from 2068 reflections
a = 14.5990 (7) Åθ = 5.1–59.5°
b = 9.5027 (5) ŵ = 0.10 mm1
c = 21.5373 (10) ÅT = 139 K
β = 95.712 (2)°Irregular, yellow
V = 2973.0 (3) Å30.51 × 0.30 × 0.19 mm
Z = 8

Data collection

Bruker APEXII diffractometer2403 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.023
graphiteθmax = 27.5°, θmin = 1.9°
[var phi] and ω scansh = −14→18
6383 measured reflectionsk = −12→9
3312 independent reflectionsl = −27→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0911P)2 + 1.065P] where P = (Fo2 + 2Fc2)/3
3312 reflections(Δ/σ)max = 0.001
216 parametersΔρmax = 1.18 e Å3
2 restraintsΔρmin = −0.27 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.60196 (9)0.52975 (15)0.49373 (6)0.0348 (3)
O21.01389 (10)0.6546 (2)0.56727 (9)0.0596 (5)
O30.95763 (10)0.75509 (18)0.64477 (7)0.0501 (5)
N10.94781 (11)0.68697 (19)0.59563 (8)0.0377 (4)
N20.53650 (11)0.61992 (16)0.59452 (7)0.0278 (4)
N30.16678 (11)0.81046 (17)0.64386 (8)0.0308 (4)
C10.68118 (12)0.56415 (18)0.51803 (8)0.0254 (4)
C20.76150 (13)0.54714 (19)0.48512 (8)0.0286 (4)
H20.75470.50850.44420.034*
C30.84661 (13)0.58457 (19)0.51059 (9)0.0283 (4)
H30.89860.57050.48800.034*
C40.85759 (12)0.64418 (19)0.57044 (9)0.0273 (4)
C50.78428 (12)0.66384 (18)0.60489 (8)0.0258 (4)
H50.79350.70370.64550.031*
C60.69633 (12)0.62481 (18)0.57975 (8)0.0241 (4)
C70.62047 (12)0.65009 (18)0.61477 (8)0.0258 (4)
H70.63210.69110.65500.031*
C80.45617 (12)0.6528 (2)0.62664 (9)0.0285 (4)
H8A0.47610.68350.66980.034*
H8B0.41770.56750.62880.034*
C90.39951 (13)0.7694 (2)0.59244 (9)0.0303 (4)
H9A0.43750.85560.59180.036*
H9B0.38230.74020.54870.036*
C100.31404 (12)0.80148 (19)0.62293 (8)0.0253 (4)
C110.22563 (13)0.77101 (19)0.60122 (9)0.0298 (4)
H110.20720.72840.56210.036*
C120.21685 (12)0.86790 (19)0.69435 (9)0.0269 (4)
C130.18875 (15)0.9262 (2)0.74883 (10)0.0391 (5)
H130.12590.92620.75670.047*
C140.25584 (18)0.9837 (3)0.79057 (10)0.0482 (6)
H140.23871.02380.82810.058*
C150.34794 (18)0.9848 (2)0.77940 (10)0.0467 (6)
H150.39231.02670.80900.056*
C160.37574 (14)0.9260 (2)0.72603 (9)0.0349 (5)
H160.43890.92650.71880.042*
C170.30999 (12)0.86553 (18)0.68270 (8)0.0240 (4)
H2N0.5301 (16)0.578 (2)0.5578 (6)0.047 (7)*
H3N0.1078 (8)0.790 (3)0.6400 (11)0.052 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0221 (7)0.0421 (8)0.0390 (8)−0.0044 (6)−0.0020 (6)−0.0080 (6)
O20.0177 (8)0.0831 (13)0.0789 (12)−0.0053 (8)0.0097 (8)−0.0235 (10)
O30.0286 (9)0.0690 (12)0.0514 (9)−0.0109 (8)−0.0022 (7)−0.0173 (8)
N10.0197 (9)0.0436 (10)0.0493 (10)−0.0028 (7)0.0012 (7)−0.0020 (8)
N20.0194 (8)0.0308 (8)0.0334 (8)0.0039 (6)0.0040 (6)−0.0015 (6)
N30.0162 (8)0.0303 (8)0.0452 (9)−0.0007 (6)0.0001 (7)−0.0016 (7)
C10.0211 (9)0.0229 (8)0.0316 (9)0.0007 (7)−0.0006 (7)0.0002 (7)
C20.0290 (10)0.0274 (9)0.0298 (9)0.0004 (8)0.0041 (8)−0.0010 (7)
C30.0229 (9)0.0273 (9)0.0357 (10)0.0014 (7)0.0076 (7)0.0024 (8)
C40.0164 (9)0.0269 (9)0.0378 (10)−0.0005 (7)−0.0007 (7)0.0025 (7)
C50.0216 (9)0.0243 (9)0.0311 (9)−0.0001 (7)0.0004 (7)0.0001 (7)
C60.0194 (9)0.0224 (8)0.0305 (9)0.0013 (7)0.0020 (7)0.0017 (7)
C70.0225 (10)0.0241 (8)0.0305 (9)0.0029 (7)0.0013 (7)0.0016 (7)
C80.0202 (10)0.0343 (10)0.0319 (9)0.0042 (7)0.0069 (7)0.0022 (7)
C90.0269 (10)0.0329 (10)0.0319 (9)0.0082 (8)0.0063 (8)0.0027 (8)
C100.0226 (9)0.0255 (8)0.0275 (9)0.0044 (7)0.0012 (7)0.0012 (7)
C110.0281 (10)0.0276 (9)0.0323 (9)0.0039 (8)−0.0047 (8)−0.0027 (7)
C120.0209 (9)0.0258 (9)0.0341 (9)0.0029 (7)0.0031 (7)0.0033 (7)
C130.0362 (12)0.0413 (11)0.0422 (11)0.0092 (9)0.0162 (9)0.0023 (9)
C140.0619 (16)0.0498 (13)0.0336 (11)0.0158 (12)0.0087 (11)−0.0085 (10)
C150.0499 (14)0.0478 (13)0.0388 (11)0.0072 (11)−0.0129 (10)−0.0144 (10)
C160.0262 (10)0.0361 (10)0.0406 (11)0.0029 (8)−0.0063 (8)−0.0047 (8)
C170.0190 (9)0.0239 (8)0.0286 (9)0.0034 (7)0.0005 (7)0.0006 (7)

Geometric parameters (Å, °)

O1—C11.264 (2)C7—H70.9500
O2—N11.231 (2)C8—C91.527 (3)
O3—N11.237 (2)C8—H8A0.9900
N1—C41.433 (2)C8—H8B0.9900
N2—C71.292 (2)C9—C101.498 (2)
N2—C81.454 (2)C9—H9A0.9900
N2—H2N0.883 (10)C9—H9B0.9900
N3—C121.363 (3)C10—C111.359 (3)
N3—C111.371 (2)C10—C171.430 (2)
N3—H3N0.879 (10)C11—H110.9500
C1—C21.439 (2)C12—C131.396 (3)
C1—C61.446 (3)C12—C171.407 (2)
C2—C31.355 (3)C13—C141.375 (3)
C2—H20.9500C13—H130.9500
C3—C41.402 (3)C14—C151.389 (4)
C3—H30.9500C14—H140.9500
C4—C51.375 (2)C15—C161.375 (3)
C5—C61.393 (3)C15—H150.9500
C5—H50.9500C16—C171.394 (3)
C6—C71.421 (2)C16—H160.9500
O2—N1—O3121.71 (18)N2—C8—H8B109.5
O2—N1—C4118.51 (17)C9—C8—H8B109.5
O3—N1—C4119.78 (16)H8A—C8—H8B108.1
C7—N2—C8125.09 (16)C10—C9—C8111.78 (14)
C7—N2—H2N114.5 (16)C10—C9—H9A109.3
C8—N2—H2N120.4 (16)C8—C9—H9A109.3
C12—N3—C11108.79 (15)C10—C9—H9B109.3
C12—N3—H3N127.4 (16)C8—C9—H9B109.3
C11—N3—H3N123.3 (16)H9A—C9—H9B107.9
O1—C1—C2121.60 (16)C11—C10—C17106.10 (15)
O1—C1—C6122.27 (16)C11—C10—C9127.56 (17)
C2—C1—C6116.12 (16)C17—C10—C9126.29 (17)
C3—C2—C1122.05 (17)C10—C11—N3110.38 (16)
C3—C2—H2119.0C10—C11—H11124.8
C1—C2—H2119.0N3—C11—H11124.8
C2—C3—C4119.64 (16)N3—C12—C13130.60 (18)
C2—C3—H3120.2N3—C12—C17107.60 (15)
C4—C3—H3120.2C13—C12—C17121.76 (19)
C5—C4—C3121.81 (17)C14—C13—C12117.22 (19)
C5—C4—N1119.53 (17)C14—C13—H13121.4
C3—C4—N1118.65 (16)C12—C13—H13121.4
C4—C5—C6119.41 (17)C13—C14—C15121.91 (19)
C4—C5—H5120.3C13—C14—H14119.0
C6—C5—H5120.3C15—C14—H14119.0
C5—C6—C7119.05 (16)C16—C15—C14120.9 (2)
C5—C6—C1120.95 (16)C16—C15—H15119.6
C7—C6—C1119.97 (16)C14—C15—H15119.6
N2—C7—C6123.14 (17)C15—C16—C17119.08 (19)
N2—C7—H7118.4C15—C16—H16120.5
C6—C7—H7118.4C17—C16—H16120.5
N2—C8—C9110.52 (14)C16—C17—C12119.15 (17)
N2—C8—H8A109.5C16—C17—C10133.65 (16)
C9—C8—H8A109.5C12—C17—C10107.12 (16)
O1—C1—C2—C3179.54 (17)C8—C9—C10—C11−108.7 (2)
C6—C1—C2—C30.6 (3)C8—C9—C10—C1768.3 (2)
C1—C2—C3—C4−1.2 (3)C17—C10—C11—N3−0.7 (2)
C2—C3—C4—C51.2 (3)C9—C10—C11—N3176.80 (17)
C2—C3—C4—N1−178.08 (17)C12—N3—C11—C100.1 (2)
O2—N1—C4—C5172.08 (18)C11—N3—C12—C13178.3 (2)
O3—N1—C4—C5−8.1 (3)C11—N3—C12—C170.5 (2)
O2—N1—C4—C3−8.7 (3)N3—C12—C13—C14−176.5 (2)
O3—N1—C4—C3171.20 (18)C17—C12—C13—C141.0 (3)
C3—C4—C5—C6−0.5 (3)C12—C13—C14—C150.2 (3)
N1—C4—C5—C6178.68 (16)C13—C14—C15—C16−0.9 (4)
C4—C5—C6—C7−177.79 (16)C14—C15—C16—C170.4 (3)
C4—C5—C6—C1−0.1 (3)C15—C16—C17—C120.8 (3)
O1—C1—C6—C5−178.92 (17)C15—C16—C17—C10177.4 (2)
C2—C1—C6—C50.1 (2)N3—C12—C17—C16176.45 (17)
O1—C1—C6—C7−1.2 (3)C13—C12—C17—C16−1.5 (3)
C2—C1—C6—C7177.77 (16)N3—C12—C17—C10−0.9 (2)
C8—N2—C7—C6−175.39 (16)C13—C12—C17—C10−178.93 (18)
C5—C6—C7—N2178.55 (16)C11—C10—C17—C16−175.9 (2)
C1—C6—C7—N20.8 (3)C9—C10—C17—C166.6 (3)
C7—N2—C8—C9109.1 (2)C11—C10—C17—C121.0 (2)
N2—C8—C9—C10177.58 (15)C9—C10—C17—C12−176.53 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2n···O10.88 (1)1.87 (2)2.602 (2)139 (2)
N3—H3n···O2i0.88 (1)2.36 (2)3.027 (2)133 (2)
N3—H3n···O3i0.88 (1)2.23 (1)3.100 (2)171 (2)

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2090).

References

  • Ali, H. M., Emmy Maryati, O. & Ng, S. W. (2007). Acta Cryst. E63, o3458.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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