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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000456X/bk1515sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000456X/bk1515Isup2.hkl
Contains datablock I

CCDC reference: 146053

Computing details top

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.

N-nitrosomelatonin top
Crystal data top
C13H15N3O3F(000) = 1104
Mr = 261.28Dx = 1.349 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 13.580 (5) ÅCell parameters from 23 reflections
b = 9.488 (2) Åθ = 9.8–15.7°
c = 20.266 (7) ŵ = 0.10 mm1
β = 99.73 (3)°T = 293 K
V = 2574 (1) Å3Triangular prism, yellow
Z = 80.44 × 0.44 × 0.28 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.011
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.0°
Graphite monochromatorh = 1717
ω/2θ scank = 012
3178 measured reflectionsl = 026
3094 independent reflections1 standard reflections every 30 min
2015 reflections with I > 2σ(I) intensity decay: 1.1%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-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 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
C10.87455 (14)0.2415 (2)0.59395 (9)0.0417 (4)
C20.88099 (13)0.2435 (2)0.52626 (9)0.0391 (4)
H20.88781 (13)0.3277 (2)0.50398 (9)0.051 (3)*
C30.87684 (13)0.1146 (2)0.49309 (8)0.0361 (4)
C40.86632 (13)0.0097 (2)0.52732 (9)0.0382 (4)
C50.85724 (14)0.0128 (2)0.59424 (9)0.0445 (4)
H50.84818 (14)0.0968 (2)0.61607 (9)0.051 (3)*
C60.8623 (2)0.1148 (2)0.62691 (9)0.0465 (5)
H60.8574 (2)0.1169 (2)0.67213 (9)0.051 (3)*
O10.87852 (12)0.35842 (15)0.63327 (7)0.0552 (4)
C70.8877 (2)0.4916 (2)0.60300 (11)0.0563 (5)
H7A0.8868 (14)0.5647 (2)0.6356 (3)0.093 (4)*
H7B0.8330 (7)0.5048 (8)0.5668 (6)0.093 (4)*
H7C0.9496 (6)0.4953 (7)0.5861 (8)0.093 (4)*
C80.88287 (13)0.0770 (2)0.42409 (8)0.0380 (4)
C90.87660 (14)0.0640 (2)0.41879 (9)0.0413 (4)
H90.87845 (14)0.1156 (2)0.38001 (9)0.051 (3)*
N10.86679 (12)0.1208 (2)0.48136 (8)0.0413 (4)
C100.8950 (2)0.1828 (2)0.37167 (9)0.0433 (4)
H10A0.9575 (2)0.2324 (2)0.38548 (9)0.050 (3)*
H10B0.8415 (2)0.2514 (2)0.36917 (9)0.050 (3)*
C110.8943 (2)0.1224 (2)0.30197 (9)0.0454 (5)
H11A0.9152 (2)0.1952 (2)0.27370 (9)0.050 (3)*
H11B0.9427 (2)0.0465 (2)0.30501 (9)0.050 (3)*
N20.79779 (13)0.0692 (2)0.27069 (7)0.0421 (4)
H2A0.78426 (13)0.0183 (2)0.27553 (7)0.051 (3)*
C120.7294 (2)0.1507 (2)0.23482 (9)0.0456 (5)
C130.6325 (2)0.0817 (3)0.20683 (11)0.0620 (6)
H13A0.6306 (6)0.0110 (8)0.2255 (7)0.093 (4)*
H13B0.6264 (6)0.0750 (17)0.15904 (14)0.093 (4)*
H13C0.5783 (2)0.1368 (10)0.2180 (8)0.093 (4)*
O20.74487 (14)0.2758 (2)0.22447 (9)0.0688 (5)
N30.86643 (14)0.2560 (2)0.50033 (9)0.0500 (4)
O30.87183 (13)0.3404 (2)0.45566 (8)0.0644 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0428 (10)0.0445 (10)0.0380 (9)0.0015 (8)0.0071 (8)0.0021 (8)
C20.0399 (9)0.0409 (9)0.0359 (9)0.0030 (8)0.0049 (7)0.0055 (7)
C30.0336 (8)0.0426 (9)0.0312 (8)0.0015 (7)0.0027 (6)0.0051 (7)
C40.0346 (9)0.0424 (10)0.0371 (9)0.0025 (7)0.0042 (7)0.0045 (8)
C50.0502 (11)0.0457 (11)0.0387 (10)0.0001 (9)0.0108 (8)0.0116 (8)
C60.0536 (11)0.0539 (12)0.0339 (9)0.0007 (9)0.0129 (8)0.0066 (8)
O10.0809 (11)0.0457 (8)0.0406 (7)0.0011 (7)0.0151 (7)0.0015 (6)
C70.0720 (14)0.0437 (11)0.0531 (12)0.0030 (10)0.0102 (10)0.0004 (9)
C80.0371 (9)0.0434 (10)0.0323 (8)0.0026 (7)0.0024 (7)0.0019 (7)
C90.0457 (10)0.0441 (10)0.0335 (9)0.0029 (8)0.0045 (7)0.0020 (8)
N10.0439 (9)0.0407 (8)0.0385 (8)0.0033 (7)0.0050 (6)0.0056 (6)
C100.0515 (11)0.0436 (10)0.0341 (9)0.0066 (8)0.0050 (8)0.0045 (8)
C110.0538 (11)0.0478 (11)0.0366 (9)0.0025 (9)0.0136 (8)0.0071 (8)
N20.0594 (10)0.0324 (8)0.0341 (7)0.0027 (7)0.0067 (7)0.0014 (6)
C120.0663 (13)0.0378 (10)0.0316 (9)0.0057 (9)0.0050 (8)0.0021 (7)
C130.0700 (15)0.0652 (14)0.0456 (12)0.0000 (12)0.0055 (10)0.0015 (11)
O20.0976 (13)0.0358 (8)0.0649 (10)0.0057 (8)0.0095 (9)0.0075 (7)
N30.0577 (10)0.0395 (9)0.0526 (10)0.0032 (8)0.0091 (8)0.0049 (8)
O30.0900 (12)0.0437 (8)0.0608 (10)0.0044 (8)0.0163 (9)0.0018 (7)
Geometric parameters (Å, º) top
C1—O11.362 (2)C8—C91.344 (3)
C1—C21.389 (3)C8—C101.491 (2)
C1—C61.398 (3)C9—N11.404 (2)
C2—C31.392 (3)N1—N31.339 (2)
C3—C41.388 (2)C10—C111.523 (3)
C3—C81.459 (2)C11—N21.447 (3)
C4—C51.383 (3)N2—C121.327 (2)
C4—N11.407 (2)C12—O21.229 (2)
C5—C61.376 (3)C12—C131.493 (3)
O1—C71.419 (2)N3—O31.221 (2)
O1—C1—C2124.3 (2)C9—C8—C10128.8 (2)
O1—C1—C6114.6 (2)C3—C8—C10123.3 (2)
C2—C1—C6121.1 (2)C8—C9—N1108.9 (2)
C1—C2—C3117.4 (2)N3—N1—C9129.2 (2)
C4—C3—C2120.3 (2)N3—N1—C4121.8 (2)
C4—C3—C8107.3 (2)C9—N1—C4108.80 (15)
C2—C3—C8132.3 (2)C8—C10—C11115.0 (2)
C5—C4—C3122.8 (2)N2—C11—C10113.6 (2)
C5—C4—N1130.1 (2)C12—N2—C11122.4 (2)
C3—C4—N1107.1 (2)O2—C12—N2122.1 (2)
C4—C5—C6116.6 (2)O2—C12—C13121.6 (2)
C5—C6—C1121.8 (2)N2—C12—C13116.3 (2)
C1—O1—C7118.0 (2)O3—N3—N1114.4 (2)
C9—C8—C3107.9 (2)
 

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