organic compounds
2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The title Schiff base, C17H15N3O3, exists in the zwitterionic form with the phenol H atom transferred to the imine group. Adjacent 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).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; 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).
Supporting information
10.1107/S1600536808011185/bv2090sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011185/bv2090Isup2.hkl
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.
The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and were included in the
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.
Data collection: APEX2 (Bruker, 2005); cell
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).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. |
C17H15N3O3 | F(000) = 1296 |
Mr = 309.32 | Dx = 1.382 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -c 2yc | Cell parameters from 2068 reflections |
a = 14.5990 (7) Å | θ = 5.1–59.5° |
b = 9.5027 (5) Å | µ = 0.10 mm−1 |
c = 21.5373 (10) Å | T = 139 K |
β = 95.712 (2)° | Irregular, yellow |
V = 2973.0 (3) Å3 | 0.51 × 0.30 × 0.19 mm |
Z = 8 |
Bruker APEXII diffractometer | 2403 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
ϕ and ω scans | h = −14→18 |
6383 measured reflections | k = −12→9 |
3312 independent reflections | l = −27→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H 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 parameters | Δρmax = 1.18 e Å−3 |
2 restraints | Δρmin = −0.27 e Å−3 |
C17H15N3O3 | V = 2973.0 (3) Å3 |
Mr = 309.32 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.5990 (7) Å | µ = 0.10 mm−1 |
b = 9.5027 (5) Å | T = 139 K |
c = 21.5373 (10) Å | 0.51 × 0.30 × 0.19 mm |
β = 95.712 (2)° |
Bruker APEXII diffractometer | 2403 reflections with I > 2σ(I) |
6383 measured reflections | Rint = 0.023 |
3312 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 2 restraints |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 1.18 e Å−3 |
3312 reflections | Δρmin = −0.27 e Å−3 |
216 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.60196 (9) | 0.52975 (15) | 0.49373 (6) | 0.0348 (3) | |
O2 | 1.01389 (10) | 0.6546 (2) | 0.56727 (9) | 0.0596 (5) | |
O3 | 0.95763 (10) | 0.75509 (18) | 0.64477 (7) | 0.0501 (5) | |
N1 | 0.94781 (11) | 0.68697 (19) | 0.59563 (8) | 0.0377 (4) | |
N2 | 0.53650 (11) | 0.61992 (16) | 0.59452 (7) | 0.0278 (4) | |
N3 | 0.16678 (11) | 0.81046 (17) | 0.64386 (8) | 0.0308 (4) | |
C1 | 0.68118 (12) | 0.56415 (18) | 0.51803 (8) | 0.0254 (4) | |
C2 | 0.76150 (13) | 0.54714 (19) | 0.48512 (8) | 0.0286 (4) | |
H2 | 0.7547 | 0.5085 | 0.4442 | 0.034* | |
C3 | 0.84661 (13) | 0.58457 (19) | 0.51059 (9) | 0.0283 (4) | |
H3 | 0.8986 | 0.5705 | 0.4880 | 0.034* | |
C4 | 0.85759 (12) | 0.64418 (19) | 0.57044 (9) | 0.0273 (4) | |
C5 | 0.78428 (12) | 0.66384 (18) | 0.60489 (8) | 0.0258 (4) | |
H5 | 0.7935 | 0.7037 | 0.6455 | 0.031* | |
C6 | 0.69633 (12) | 0.62481 (18) | 0.57975 (8) | 0.0241 (4) | |
C7 | 0.62047 (12) | 0.65009 (18) | 0.61477 (8) | 0.0258 (4) | |
H7 | 0.6321 | 0.6911 | 0.6550 | 0.031* | |
C8 | 0.45617 (12) | 0.6528 (2) | 0.62664 (9) | 0.0285 (4) | |
H8A | 0.4761 | 0.6835 | 0.6698 | 0.034* | |
H8B | 0.4177 | 0.5675 | 0.6288 | 0.034* | |
C9 | 0.39951 (13) | 0.7694 (2) | 0.59244 (9) | 0.0303 (4) | |
H9A | 0.4375 | 0.8556 | 0.5918 | 0.036* | |
H9B | 0.3823 | 0.7402 | 0.5487 | 0.036* | |
C10 | 0.31404 (12) | 0.80148 (19) | 0.62293 (8) | 0.0253 (4) | |
C11 | 0.22563 (13) | 0.77101 (19) | 0.60122 (9) | 0.0298 (4) | |
H11 | 0.2072 | 0.7284 | 0.5621 | 0.036* | |
C12 | 0.21685 (12) | 0.86790 (19) | 0.69435 (9) | 0.0269 (4) | |
C13 | 0.18875 (15) | 0.9262 (2) | 0.74883 (10) | 0.0391 (5) | |
H13 | 0.1259 | 0.9262 | 0.7567 | 0.047* | |
C14 | 0.25584 (18) | 0.9837 (3) | 0.79057 (10) | 0.0482 (6) | |
H14 | 0.2387 | 1.0238 | 0.8281 | 0.058* | |
C15 | 0.34794 (18) | 0.9848 (2) | 0.77940 (10) | 0.0467 (6) | |
H15 | 0.3923 | 1.0267 | 0.8090 | 0.056* | |
C16 | 0.37574 (14) | 0.9260 (2) | 0.72603 (9) | 0.0349 (5) | |
H16 | 0.4389 | 0.9265 | 0.7188 | 0.042* | |
C17 | 0.30999 (12) | 0.86553 (18) | 0.68270 (8) | 0.0240 (4) | |
H2N | 0.5301 (16) | 0.578 (2) | 0.5578 (6) | 0.047 (7)* | |
H3N | 0.1078 (8) | 0.790 (3) | 0.6400 (11) | 0.052 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0221 (7) | 0.0421 (8) | 0.0390 (8) | −0.0044 (6) | −0.0020 (6) | −0.0080 (6) |
O2 | 0.0177 (8) | 0.0831 (13) | 0.0789 (12) | −0.0053 (8) | 0.0097 (8) | −0.0235 (10) |
O3 | 0.0286 (9) | 0.0690 (12) | 0.0514 (9) | −0.0109 (8) | −0.0022 (7) | −0.0173 (8) |
N1 | 0.0197 (9) | 0.0436 (10) | 0.0493 (10) | −0.0028 (7) | 0.0012 (7) | −0.0020 (8) |
N2 | 0.0194 (8) | 0.0308 (8) | 0.0334 (8) | 0.0039 (6) | 0.0040 (6) | −0.0015 (6) |
N3 | 0.0162 (8) | 0.0303 (8) | 0.0452 (9) | −0.0007 (6) | 0.0001 (7) | −0.0016 (7) |
C1 | 0.0211 (9) | 0.0229 (8) | 0.0316 (9) | 0.0007 (7) | −0.0006 (7) | 0.0002 (7) |
C2 | 0.0290 (10) | 0.0274 (9) | 0.0298 (9) | 0.0004 (8) | 0.0041 (8) | −0.0010 (7) |
C3 | 0.0229 (9) | 0.0273 (9) | 0.0357 (10) | 0.0014 (7) | 0.0076 (7) | 0.0024 (8) |
C4 | 0.0164 (9) | 0.0269 (9) | 0.0378 (10) | −0.0005 (7) | −0.0007 (7) | 0.0025 (7) |
C5 | 0.0216 (9) | 0.0243 (9) | 0.0311 (9) | −0.0001 (7) | 0.0004 (7) | 0.0001 (7) |
C6 | 0.0194 (9) | 0.0224 (8) | 0.0305 (9) | 0.0013 (7) | 0.0020 (7) | 0.0017 (7) |
C7 | 0.0225 (10) | 0.0241 (8) | 0.0305 (9) | 0.0029 (7) | 0.0013 (7) | 0.0016 (7) |
C8 | 0.0202 (10) | 0.0343 (10) | 0.0319 (9) | 0.0042 (7) | 0.0069 (7) | 0.0022 (7) |
C9 | 0.0269 (10) | 0.0329 (10) | 0.0319 (9) | 0.0082 (8) | 0.0063 (8) | 0.0027 (8) |
C10 | 0.0226 (9) | 0.0255 (8) | 0.0275 (9) | 0.0044 (7) | 0.0012 (7) | 0.0012 (7) |
C11 | 0.0281 (10) | 0.0276 (9) | 0.0323 (9) | 0.0039 (8) | −0.0047 (8) | −0.0027 (7) |
C12 | 0.0209 (9) | 0.0258 (9) | 0.0341 (9) | 0.0029 (7) | 0.0031 (7) | 0.0033 (7) |
C13 | 0.0362 (12) | 0.0413 (11) | 0.0422 (11) | 0.0092 (9) | 0.0162 (9) | 0.0023 (9) |
C14 | 0.0619 (16) | 0.0498 (13) | 0.0336 (11) | 0.0158 (12) | 0.0087 (11) | −0.0085 (10) |
C15 | 0.0499 (14) | 0.0478 (13) | 0.0388 (11) | 0.0072 (11) | −0.0129 (10) | −0.0144 (10) |
C16 | 0.0262 (10) | 0.0361 (10) | 0.0406 (11) | 0.0029 (8) | −0.0063 (8) | −0.0047 (8) |
C17 | 0.0190 (9) | 0.0239 (8) | 0.0286 (9) | 0.0034 (7) | 0.0005 (7) | 0.0006 (7) |
O1—C1 | 1.264 (2) | C7—H7 | 0.9500 |
O2—N1 | 1.231 (2) | C8—C9 | 1.527 (3) |
O3—N1 | 1.237 (2) | C8—H8A | 0.9900 |
N1—C4 | 1.433 (2) | C8—H8B | 0.9900 |
N2—C7 | 1.292 (2) | C9—C10 | 1.498 (2) |
N2—C8 | 1.454 (2) | C9—H9A | 0.9900 |
N2—H2N | 0.883 (10) | C9—H9B | 0.9900 |
N3—C12 | 1.363 (3) | C10—C11 | 1.359 (3) |
N3—C11 | 1.371 (2) | C10—C17 | 1.430 (2) |
N3—H3N | 0.879 (10) | C11—H11 | 0.9500 |
C1—C2 | 1.439 (2) | C12—C13 | 1.396 (3) |
C1—C6 | 1.446 (3) | C12—C17 | 1.407 (2) |
C2—C3 | 1.355 (3) | C13—C14 | 1.375 (3) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C4 | 1.402 (3) | C14—C15 | 1.389 (4) |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.375 (2) | C15—C16 | 1.375 (3) |
C5—C6 | 1.393 (3) | C15—H15 | 0.9500 |
C5—H5 | 0.9500 | C16—C17 | 1.394 (3) |
C6—C7 | 1.421 (2) | C16—H16 | 0.9500 |
O2—N1—O3 | 121.71 (18) | N2—C8—H8B | 109.5 |
O2—N1—C4 | 118.51 (17) | C9—C8—H8B | 109.5 |
O3—N1—C4 | 119.78 (16) | H8A—C8—H8B | 108.1 |
C7—N2—C8 | 125.09 (16) | C10—C9—C8 | 111.78 (14) |
C7—N2—H2N | 114.5 (16) | C10—C9—H9A | 109.3 |
C8—N2—H2N | 120.4 (16) | C8—C9—H9A | 109.3 |
C12—N3—C11 | 108.79 (15) | C10—C9—H9B | 109.3 |
C12—N3—H3N | 127.4 (16) | C8—C9—H9B | 109.3 |
C11—N3—H3N | 123.3 (16) | H9A—C9—H9B | 107.9 |
O1—C1—C2 | 121.60 (16) | C11—C10—C17 | 106.10 (15) |
O1—C1—C6 | 122.27 (16) | C11—C10—C9 | 127.56 (17) |
C2—C1—C6 | 116.12 (16) | C17—C10—C9 | 126.29 (17) |
C3—C2—C1 | 122.05 (17) | C10—C11—N3 | 110.38 (16) |
C3—C2—H2 | 119.0 | C10—C11—H11 | 124.8 |
C1—C2—H2 | 119.0 | N3—C11—H11 | 124.8 |
C2—C3—C4 | 119.64 (16) | N3—C12—C13 | 130.60 (18) |
C2—C3—H3 | 120.2 | N3—C12—C17 | 107.60 (15) |
C4—C3—H3 | 120.2 | C13—C12—C17 | 121.76 (19) |
C5—C4—C3 | 121.81 (17) | C14—C13—C12 | 117.22 (19) |
C5—C4—N1 | 119.53 (17) | C14—C13—H13 | 121.4 |
C3—C4—N1 | 118.65 (16) | C12—C13—H13 | 121.4 |
C4—C5—C6 | 119.41 (17) | C13—C14—C15 | 121.91 (19) |
C4—C5—H5 | 120.3 | C13—C14—H14 | 119.0 |
C6—C5—H5 | 120.3 | C15—C14—H14 | 119.0 |
C5—C6—C7 | 119.05 (16) | C16—C15—C14 | 120.9 (2) |
C5—C6—C1 | 120.95 (16) | C16—C15—H15 | 119.6 |
C7—C6—C1 | 119.97 (16) | C14—C15—H15 | 119.6 |
N2—C7—C6 | 123.14 (17) | C15—C16—C17 | 119.08 (19) |
N2—C7—H7 | 118.4 | C15—C16—H16 | 120.5 |
C6—C7—H7 | 118.4 | C17—C16—H16 | 120.5 |
N2—C8—C9 | 110.52 (14) | C16—C17—C12 | 119.15 (17) |
N2—C8—H8A | 109.5 | C16—C17—C10 | 133.65 (16) |
C9—C8—H8A | 109.5 | C12—C17—C10 | 107.12 (16) |
O1—C1—C2—C3 | 179.54 (17) | C8—C9—C10—C11 | −108.7 (2) |
C6—C1—C2—C3 | 0.6 (3) | C8—C9—C10—C17 | 68.3 (2) |
C1—C2—C3—C4 | −1.2 (3) | C17—C10—C11—N3 | −0.7 (2) |
C2—C3—C4—C5 | 1.2 (3) | C9—C10—C11—N3 | 176.80 (17) |
C2—C3—C4—N1 | −178.08 (17) | C12—N3—C11—C10 | 0.1 (2) |
O2—N1—C4—C5 | 172.08 (18) | C11—N3—C12—C13 | 178.3 (2) |
O3—N1—C4—C5 | −8.1 (3) | C11—N3—C12—C17 | 0.5 (2) |
O2—N1—C4—C3 | −8.7 (3) | N3—C12—C13—C14 | −176.5 (2) |
O3—N1—C4—C3 | 171.20 (18) | C17—C12—C13—C14 | 1.0 (3) |
C3—C4—C5—C6 | −0.5 (3) | C12—C13—C14—C15 | 0.2 (3) |
N1—C4—C5—C6 | 178.68 (16) | C13—C14—C15—C16 | −0.9 (4) |
C4—C5—C6—C7 | −177.79 (16) | C14—C15—C16—C17 | 0.4 (3) |
C4—C5—C6—C1 | −0.1 (3) | C15—C16—C17—C12 | 0.8 (3) |
O1—C1—C6—C5 | −178.92 (17) | C15—C16—C17—C10 | 177.4 (2) |
C2—C1—C6—C5 | 0.1 (2) | N3—C12—C17—C16 | 176.45 (17) |
O1—C1—C6—C7 | −1.2 (3) | C13—C12—C17—C16 | −1.5 (3) |
C2—C1—C6—C7 | 177.77 (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—N2 | 178.55 (16) | C11—C10—C17—C16 | −175.9 (2) |
C1—C6—C7—N2 | 0.8 (3) | C9—C10—C17—C16 | 6.6 (3) |
C7—N2—C8—C9 | 109.1 (2) | C11—C10—C17—C12 | 1.0 (2) |
N2—C8—C9—C10 | 177.58 (15) | C9—C10—C17—C12 | −176.53 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O1 | 0.88 (1) | 1.87 (2) | 2.602 (2) | 139 (2) |
N3—H3n···O2i | 0.88 (1) | 2.36 (2) | 3.027 (2) | 133 (2) |
N3—H3n···O3i | 0.88 (1) | 2.23 (1) | 3.100 (2) | 171 (2) |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H15N3O3 |
Mr | 309.32 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 139 |
a, b, c (Å) | 14.5990 (7), 9.5027 (5), 21.5373 (10) |
β (°) | 95.712 (2) |
V (Å3) | 2973.0 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.51 × 0.30 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6383, 3312, 2403 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.161, 1.06 |
No. of reflections | 3312 |
No. of parameters | 216 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.18, −0.27 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O1 | 0.88 (1) | 1.87 (2) | 2.602 (2) | 139 (2) |
N3—H3n···O2i | 0.88 (1) | 2.36 (2) | 3.027 (2) | 133 (2) |
N3—H3n···O3i | 0.88 (1) | 2.23 (1) | 3.100 (2) | 171 (2) |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
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
Ali, H. M., Emmy Maryati, O. & Ng, S. W. (2007). Acta Cryst. E63, o3458. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
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