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Acta Cryst. (2008). E64, o913    [ doi:10.1107/S1600536808011185 ]

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

H. M. Ali, M. I. Mohamed Mustafa, M. R. Rizal and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate top
Crystal data top
C17H15N3O3F(000) = 1296
Mr = 309.32Dx = 1.382 Mg m−3
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 mm−1
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 top
Bruker APEXII
diffractometer		2403 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.023
graphiteθmax = 27.5°, θmin = 1.9°
φ and ω scansh = −14→18
6383 measured reflectionsk = −12→9
3312 independent reflectionsl = −27→26
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 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 Å−3
2 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C17H15N3O3V = 2973.0 (3) Å3
Mr = 309.32Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.5990 (7) ŵ = 0.10 mm−1
b = 9.5027 (5) ÅT = 139 K
c = 21.5373 (10) Å0.51 × 0.30 × 0.19 mm
β = 95.712 (2)°
Data collection top
Bruker APEXII
diffractometer		Rint = 0.023
6383 measured reflectionsθmax = 27.5°
3312 independent reflectionsStandard reflections: 0
2403 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161Δρmax = 1.18 e Å−3
S = 1.06Δρmin = −0.27 e Å−3
3312 reflectionsAbsolute structure: ?
216 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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.

references
References top

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.

Westrip, S. P. (2008). publCIF. In preparation.