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The crystal structure of the title compound, C16H11N3O3, has been determined from X-ray powder data. The mol­ecule is slightly non-planar. The structure adopts a stacking arrangement, with the stacks extended along [001]. The AM1 calculations of the crystal electrostatic potential show that the crystal environment causes only a moderate (23%) increase in the molecular dipole moment of the title compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018268/ya6065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018268/ya6065Isup2.hkl
Contains datablock I

CCDC reference: 177198

Key indicators

  • Powder X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.045
  • wR factor = 0.060

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: local program; cell refinement: LSPAID (Visser, 1986); program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; molecular graphics: PLUTON (Spek, 1992); software used to prepare material for publication: PARST (Nardelli, 1983).

1-[(2-nitrophenyl)hydrazono]-1H-naphthalen-2-one top
Crystal data top
C16H11N3O3F(000) = 608
Mr = 293.28Dx = 1.446 Mg m3
Orthorhombic, P212121Melting point: 487 K
a = 15.036 (5) ÅCu Kα radiation, λ = 1.5418 Å
b = 12.722 (4) ÅT = 295 K
c = 7.042 (3) ÅParticle morphology: fibre-like needles
V = 1347.1 (8) Å3orange-red
Z = 4flat_sheet, 25 × 25 mm
Data collection top
DRON-3M
diffractometer (Burevestnik, Russia)
Data collection mode: reflection
Radiation source: X-ray sealed tubeScan method: step
Ni filtered monochromator2θmin = 8.0°, 2θmax = 66.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder
Refinement top
Refinement on Inet112 parameters
Least-squares matrix: full with fixed elements per cycle14 restraints
Rp = 0.0450 constraints
Rwp = 0.060H-atom parameters not refined
Rexp = 0.016Weighting scheme based on measured s.u.'s
3101 data points(Δ/σ)max = 0.042
Excluded region(s): 66.02 - 70.0Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-VoigtPreferred orientation correction: March-Dollase (Dollase, 1986) along [001], G1 = 1.210(1)
Special details top

Experimental. specimen was rotated in its plane

Refinement. Hydrogen atoms were placed in calculated positions. The planarity of the phenyl and nitro groups and of the naphthalene fragment was restrained.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1068 (3)0.5962 (4)0.1680 (7)0.094 (2)*
O20.2187 (3)0.7735 (4)0.0969 (11)0.110 (2)*
O30.3150 (4)0.8961 (3)0.0785 (11)0.110 (2)*
N10.2717 (3)0.5780 (4)0.1271 (9)0.062 (2)*
N20.2677 (4)0.4717 (5)0.1146 (7)0.062 (2)*
N30.2957 (3)0.8031 (3)0.0932 (9)0.110 (2)*
C10.1843 (3)0.4366 (3)0.1272 (5)0.094 (2)*
C20.1008 (3)0.4962 (3)0.1551 (8)0.094 (2)*
C30.0164 (3)0.4387 (3)0.1684 (9)0.094 (2)*
C40.0131 (3)0.3350 (3)0.1522 (7)0.094 (2)*
C50.0869 (3)0.1652 (4)0.1082 (9)0.094 (2)*
C60.1625 (3)0.1050 (3)0.0817 (6)0.094 (2)*
C70.2468 (3)0.1537 (3)0.0677 (8)0.094 (2)*
C80.2547 (3)0.2622 (3)0.0827 (8)0.094 (2)*
C90.1782 (3)0.3231 (3)0.1123 (8)0.094 (2)*
C100.0937 (3)0.2751 (3)0.1226 (7)0.094 (2)*
C110.3558 (3)0.6169 (4)0.1309 (9)0.062 (2)*
C120.3693 (3)0.7258 (4)0.1181 (7)0.062 (2)*
C130.4559 (3)0.7671 (3)0.1258 (10)0.062 (2)*
C140.5279 (3)0.7012 (3)0.1426 (8)0.062 (2)*
C150.5144 (3)0.5924 (3)0.1549 (10)0.062 (2)*
C160.4299 (3)0.5506 (3)0.1550 (9)0.062 (2)*
H10.22360.61860.14470.074*
H30.03360.48390.18670.11*
H40.03980.29330.15900.11*
H50.03000.13350.11820.11*
H60.15930.03080.07180.11*
H70.29740.11080.04940.11*
H80.31090.29550.07500.11*
H130.46350.84110.11290.074*
H140.58700.72800.14370.074*
H150.56500.54790.17030.074*
H160.42000.47720.16880.074*
Geometric parameters (Å, º) top
O1—C21.279 (6)C11—C121.403 (7)
O2—N31.218 (6)C11—C161.408 (6)
O3—N31.223 (6)C12—C131.405 (6)
N1—N21.357 (8)C13—C141.374 (6)
N1—C111.358 (7)C14—C151.402 (6)
N2—C11.334 (8)C15—C161.377 (6)
N3—C121.491 (6)N1—H10.897
C1—C21.480 (6)C3—H30.955
C1—C91.451 (5)C4—H40.957
C2—C31.468 (6)C5—H50.949
C3—C41.325 (5)C6—H60.948
C4—C101.447 (6)C7—H70.945
C5—C61.383 (6)C8—H80.947
C5—C101.406 (6)C13—H130.953
C6—C71.414 (6)C14—H140.952
C7—C81.390 (5)C15—H150.955
C8—C91.402 (6)C16—H160.951
C9—C101.412 (6)
N2—N1—C11113.9 (5)N3—C12—C13116.5 (4)
N1—N2—C1111.8 (5)C12—C13—C14120.3 (4)
O2—N3—O3121.8 (5)C13—C14—C15119.6 (4)
O3—N3—C12118.2 (4)C14—C15—C16121.0 (4)
O2—N3—C12120.0 (4)C11—C16—C15119.9 (4)
N2—C1—C9112.8 (4)C11—N1—H1122.5
N2—C1—C2129.4 (5)N2—N1—H1123.2
C2—C1—C9117.8 (3)C2—C3—H3112.9
O1—C2—C1117.4 (4)C4—C3—H3125.6
C1—C2—C3119.1 (4)C3—C4—H4125.4
O1—C2—C3123.5 (4)C10—C4—H4114.3
C2—C3—C4121.5 (4)C10—C5—H5118.9
C3—C4—C10120.4 (4)C6—C5—H5121.1
C6—C5—C10120.1 (4)C7—C6—H6118.5
C5—C6—C7120.2 (4)C5—C6—H6121.3
C6—C7—C8120.4 (4)C8—C7—H7121.0
C7—C8—C9119.3 (4)C6—C7—H7118.6
C1—C9—C8120.6 (4)C7—C8—H8121.1
C8—C9—C10120.5 (4)C9—C8—H8119.6
C1—C9—C10118.9 (4)C12—C13—H13118.5
C5—C10—C9119.5 (4)C14—C13—H13121.1
C4—C10—C9122.3 (4)C13—C14—H14121.2
C4—C10—C5118.3 (4)C15—C14—H14119.2
N1—C11—C16121.4 (4)C14—C15—H15118.5
N1—C11—C12119.6 (5)C16—C15—H15120.4
C12—C11—C16119.0 (4)C15—C16—H16121.6
N3—C12—C11123.5 (4)C11—C16—H16118.5
C11—C12—C13120.1 (4)
 

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