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The title compound, N-[2-(5-methoxy-1-nitroso-1H-indol-3-yl)ethyl]acetamide, C13H15N3O3, an N-nitroso derivative of melatonin, crystallizes in the monoclinic C2/c space group. The molecules are arranged in such a way that the aromatic rings are in a planar conformation, with the alkylamide side chains in a different plane, at a dihedral angle of 108.60 (6)°. The alkylamide chains are interconnected by hydrogen bonds, constituting an infinite array.
Supporting information
CCDC reference: 146053
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP (Frenz, 1983); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL93.
Crystal data top
C13H15N3O3 | F(000) = 1104 |
Mr = 261.28 | Dx = 1.349 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.580 (5) Å | Cell parameters from 23 reflections |
b = 9.488 (2) Å | θ = 9.8–15.7° |
c = 20.266 (7) Å | µ = 0.10 mm−1 |
β = 99.73 (3)° | T = 293 K |
V = 2574 (1) Å3 | Triangular prism, yellow |
Z = 8 | 0.44 × 0.44 × 0.28 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | Rint = 0.011 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.0° |
Graphite monochromator | h = −17→17 |
ω/2θ scan | k = 0→12 |
3178 measured reflections | l = 0→26 |
3094 independent reflections | 1 standard reflections every 30 min |
2015 reflections with I > 2σ(I) | intensity decay: 1.1% |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0594P)2 + 1.79P] where P = (Fo2 + 2Fc2)/3 |
3085 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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. |
Refinement. Refinement on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > 2σ(F2) is used only for calculating R factor
obs 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.87455 (14) | 0.2415 (2) | 0.59395 (9) | 0.0417 (4) | |
C2 | 0.88099 (13) | 0.2435 (2) | 0.52626 (9) | 0.0391 (4) | |
H2 | 0.88781 (13) | 0.3277 (2) | 0.50398 (9) | 0.051 (3)* | |
C3 | 0.87684 (13) | 0.1146 (2) | 0.49309 (8) | 0.0361 (4) | |
C4 | 0.86632 (13) | −0.0097 (2) | 0.52732 (9) | 0.0382 (4) | |
C5 | 0.85724 (14) | −0.0128 (2) | 0.59424 (9) | 0.0445 (4) | |
H5 | 0.84818 (14) | −0.0968 (2) | 0.61607 (9) | 0.051 (3)* | |
C6 | 0.8623 (2) | 0.1148 (2) | 0.62691 (9) | 0.0465 (5) | |
H6 | 0.8574 (2) | 0.1169 (2) | 0.67213 (9) | 0.051 (3)* | |
O1 | 0.87852 (12) | 0.35842 (15) | 0.63327 (7) | 0.0552 (4) | |
C7 | 0.8877 (2) | 0.4916 (2) | 0.60300 (11) | 0.0563 (5) | |
H7A | 0.8868 (14) | 0.5647 (2) | 0.6356 (3) | 0.093 (4)* | |
H7B | 0.8330 (7) | 0.5048 (8) | 0.5668 (6) | 0.093 (4)* | |
H7C | 0.9496 (6) | 0.4953 (7) | 0.5861 (8) | 0.093 (4)* | |
C8 | 0.88287 (13) | 0.0770 (2) | 0.42409 (8) | 0.0380 (4) | |
C9 | 0.87660 (14) | −0.0640 (2) | 0.41879 (9) | 0.0413 (4) | |
H9 | 0.87845 (14) | −0.1156 (2) | 0.38001 (9) | 0.051 (3)* | |
N1 | 0.86679 (12) | −0.1208 (2) | 0.48136 (8) | 0.0413 (4) | |
C10 | 0.8950 (2) | 0.1828 (2) | 0.37167 (9) | 0.0433 (4) | |
H10A | 0.9575 (2) | 0.2324 (2) | 0.38548 (9) | 0.050 (3)* | |
H10B | 0.8415 (2) | 0.2514 (2) | 0.36917 (9) | 0.050 (3)* | |
C11 | 0.8943 (2) | 0.1224 (2) | 0.30197 (9) | 0.0454 (5) | |
H11A | 0.9152 (2) | 0.1952 (2) | 0.27370 (9) | 0.050 (3)* | |
H11B | 0.9427 (2) | 0.0465 (2) | 0.30501 (9) | 0.050 (3)* | |
N2 | 0.79779 (13) | 0.0692 (2) | 0.27069 (7) | 0.0421 (4) | |
H2A | 0.78426 (13) | −0.0183 (2) | 0.27553 (7) | 0.051 (3)* | |
C12 | 0.7294 (2) | 0.1507 (2) | 0.23482 (9) | 0.0456 (5) | |
C13 | 0.6325 (2) | 0.0817 (3) | 0.20683 (11) | 0.0620 (6) | |
H13A | 0.6306 (6) | −0.0110 (8) | 0.2255 (7) | 0.093 (4)* | |
H13B | 0.6264 (6) | 0.0750 (17) | 0.15904 (14) | 0.093 (4)* | |
H13C | 0.5783 (2) | 0.1368 (10) | 0.2180 (8) | 0.093 (4)* | |
O2 | 0.74487 (14) | 0.2758 (2) | 0.22447 (9) | 0.0688 (5) | |
N3 | 0.86643 (14) | −0.2560 (2) | 0.50033 (9) | 0.0500 (4) | |
O3 | 0.87183 (13) | −0.3404 (2) | 0.45566 (8) | 0.0644 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0428 (10) | 0.0445 (10) | 0.0380 (9) | 0.0015 (8) | 0.0071 (8) | 0.0021 (8) |
C2 | 0.0399 (9) | 0.0409 (9) | 0.0359 (9) | −0.0030 (8) | 0.0049 (7) | 0.0055 (7) |
C3 | 0.0336 (8) | 0.0426 (9) | 0.0312 (8) | −0.0015 (7) | 0.0027 (6) | 0.0051 (7) |
C4 | 0.0346 (9) | 0.0424 (10) | 0.0371 (9) | −0.0025 (7) | 0.0042 (7) | 0.0045 (8) |
C5 | 0.0502 (11) | 0.0457 (11) | 0.0387 (10) | −0.0001 (9) | 0.0108 (8) | 0.0116 (8) |
C6 | 0.0536 (11) | 0.0539 (12) | 0.0339 (9) | 0.0007 (9) | 0.0129 (8) | 0.0066 (8) |
O1 | 0.0809 (11) | 0.0457 (8) | 0.0406 (7) | −0.0011 (7) | 0.0151 (7) | −0.0015 (6) |
C7 | 0.0720 (14) | 0.0437 (11) | 0.0531 (12) | −0.0030 (10) | 0.0102 (10) | −0.0004 (9) |
C8 | 0.0371 (9) | 0.0434 (10) | 0.0323 (8) | −0.0026 (7) | 0.0024 (7) | 0.0019 (7) |
C9 | 0.0457 (10) | 0.0441 (10) | 0.0335 (9) | −0.0029 (8) | 0.0045 (7) | 0.0020 (8) |
N1 | 0.0439 (9) | 0.0407 (8) | 0.0385 (8) | −0.0033 (7) | 0.0050 (6) | 0.0056 (6) |
C10 | 0.0515 (11) | 0.0436 (10) | 0.0341 (9) | −0.0066 (8) | 0.0050 (8) | 0.0045 (8) |
C11 | 0.0538 (11) | 0.0478 (11) | 0.0366 (9) | 0.0025 (9) | 0.0136 (8) | 0.0071 (8) |
N2 | 0.0594 (10) | 0.0324 (8) | 0.0341 (7) | 0.0027 (7) | 0.0067 (7) | 0.0014 (6) |
C12 | 0.0663 (13) | 0.0378 (10) | 0.0316 (9) | 0.0057 (9) | 0.0050 (8) | −0.0021 (7) |
C13 | 0.0700 (15) | 0.0652 (14) | 0.0456 (12) | 0.0000 (12) | −0.0055 (10) | 0.0015 (11) |
O2 | 0.0976 (13) | 0.0358 (8) | 0.0649 (10) | 0.0057 (8) | −0.0095 (9) | 0.0075 (7) |
N3 | 0.0577 (10) | 0.0395 (9) | 0.0526 (10) | −0.0032 (8) | 0.0091 (8) | 0.0049 (8) |
O3 | 0.0900 (12) | 0.0437 (8) | 0.0608 (10) | −0.0044 (8) | 0.0163 (9) | −0.0018 (7) |
Geometric parameters (Å, º) top
C1—O1 | 1.362 (2) | C8—C9 | 1.344 (3) |
C1—C2 | 1.389 (3) | C8—C10 | 1.491 (2) |
C1—C6 | 1.398 (3) | C9—N1 | 1.404 (2) |
C2—C3 | 1.392 (3) | N1—N3 | 1.339 (2) |
C3—C4 | 1.388 (2) | C10—C11 | 1.523 (3) |
C3—C8 | 1.459 (2) | C11—N2 | 1.447 (3) |
C4—C5 | 1.383 (3) | N2—C12 | 1.327 (2) |
C4—N1 | 1.407 (2) | C12—O2 | 1.229 (2) |
C5—C6 | 1.376 (3) | C12—C13 | 1.493 (3) |
O1—C7 | 1.419 (2) | N3—O3 | 1.221 (2) |
| | | |
O1—C1—C2 | 124.3 (2) | C9—C8—C10 | 128.8 (2) |
O1—C1—C6 | 114.6 (2) | C3—C8—C10 | 123.3 (2) |
C2—C1—C6 | 121.1 (2) | C8—C9—N1 | 108.9 (2) |
C1—C2—C3 | 117.4 (2) | N3—N1—C9 | 129.2 (2) |
C4—C3—C2 | 120.3 (2) | N3—N1—C4 | 121.8 (2) |
C4—C3—C8 | 107.3 (2) | C9—N1—C4 | 108.80 (15) |
C2—C3—C8 | 132.3 (2) | C8—C10—C11 | 115.0 (2) |
C5—C4—C3 | 122.8 (2) | N2—C11—C10 | 113.6 (2) |
C5—C4—N1 | 130.1 (2) | C12—N2—C11 | 122.4 (2) |
C3—C4—N1 | 107.1 (2) | O2—C12—N2 | 122.1 (2) |
C4—C5—C6 | 116.6 (2) | O2—C12—C13 | 121.6 (2) |
C5—C6—C1 | 121.8 (2) | N2—C12—C13 | 116.3 (2) |
C1—O1—C7 | 118.0 (2) | O3—N3—N1 | 114.4 (2) |
C9—C8—C3 | 107.9 (2) | | |
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