1-[(2-Nitro­phenyl)­hydrazono]-1H-naphthalen-2-one (Pigment Orange 2) from powder data

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.

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

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Computing details

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

Crystal data

C16H11N3O3	F(000) = 608
Mr = 293.28	Dx = 1.446 Mg m^−3
Orthorhombic, P212121	Melting point: 487 K
a = 15.036 (5) Å	Cu Kα radiation, λ = 1.5418 Å
b = 12.722 (4) Å	T = 295 K
c = 7.042 (3) Å	Particle morphology: fibre-like needles
V = 1347.1 (8) Å^3	orange-red
Z = 4	flat_sheet, 25 × 25 mm

Data collection

DRON-3M diffractometer (Burevestnik, Russia)	Data collection mode: reflection
Radiation source: X-ray sealed tube	Scan method: step
Ni filtered monochromator	2θmin = 8.0°, 2θmax = 66.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder

Refinement

Refinement on Inet	112 parameters
Least-squares matrix: full with fixed elements per cycle	14 restraints
Rp = 0.045	0 constraints
Rwp = 0.060	H-atom parameters not refined
Rexp = 0.016	Weighting scheme based on measured s.u.'s
3101 data points	(Δ/σ)max = 0.042
Excluded region(s): 66.02 - 70.0	Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt	Preferred orientation correction: March-Dollase (Dollase, 1986) along [001], G1 = 1.210(1)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1068 (3)	0.5962 (4)	0.1680 (7)	0.094 (2)*
O2	0.2187 (3)	0.7735 (4)	0.0969 (11)	0.110 (2)*
O3	0.3150 (4)	0.8961 (3)	0.0785 (11)	0.110 (2)*
N1	0.2717 (3)	0.5780 (4)	0.1271 (9)	0.062 (2)*
N2	0.2677 (4)	0.4717 (5)	0.1146 (7)	0.062 (2)*
N3	0.2957 (3)	0.8031 (3)	0.0932 (9)	0.110 (2)*
C1	0.1843 (3)	0.4366 (3)	0.1272 (5)	0.094 (2)*
C2	0.1008 (3)	0.4962 (3)	0.1551 (8)	0.094 (2)*
C3	0.0164 (3)	0.4387 (3)	0.1684 (9)	0.094 (2)*
C4	0.0131 (3)	0.3350 (3)	0.1522 (7)	0.094 (2)*
C5	0.0869 (3)	0.1652 (4)	0.1082 (9)	0.094 (2)*
C6	0.1625 (3)	0.1050 (3)	0.0817 (6)	0.094 (2)*
C7	0.2468 (3)	0.1537 (3)	0.0677 (8)	0.094 (2)*
C8	0.2547 (3)	0.2622 (3)	0.0827 (8)	0.094 (2)*
C9	0.1782 (3)	0.3231 (3)	0.1123 (8)	0.094 (2)*
C10	0.0937 (3)	0.2751 (3)	0.1226 (7)	0.094 (2)*
C11	0.3558 (3)	0.6169 (4)	0.1309 (9)	0.062 (2)*
C12	0.3693 (3)	0.7258 (4)	0.1181 (7)	0.062 (2)*
C13	0.4559 (3)	0.7671 (3)	0.1258 (10)	0.062 (2)*
C14	0.5279 (3)	0.7012 (3)	0.1426 (8)	0.062 (2)*
C15	0.5144 (3)	0.5924 (3)	0.1549 (10)	0.062 (2)*
C16	0.4299 (3)	0.5506 (3)	0.1550 (9)	0.062 (2)*
H1	0.2236	0.6186	0.1447	0.074*
H3	−0.0336	0.4839	0.1867	0.11*
H4	−0.0398	0.2933	0.1590	0.11*
H5	0.0300	0.1335	0.1182	0.11*
H6	0.1593	0.0308	0.0718	0.11*
H7	0.2974	0.1108	0.0494	0.11*
H8	0.3109	0.2955	0.0750	0.11*
H13	0.4635	0.8411	0.1129	0.074*
H14	0.5870	0.7280	0.1437	0.074*
H15	0.5650	0.5479	0.1703	0.074*
H16	0.4200	0.4772	0.1688	0.074*

Geometric parameters (Å, º)

O1—C2	1.279 (6)	C11—C12	1.403 (7)
O2—N3	1.218 (6)	C11—C16	1.408 (6)
O3—N3	1.223 (6)	C12—C13	1.405 (6)
N1—N2	1.357 (8)	C13—C14	1.374 (6)
N1—C11	1.358 (7)	C14—C15	1.402 (6)
N2—C1	1.334 (8)	C15—C16	1.377 (6)
N3—C12	1.491 (6)	N1—H1	0.897
C1—C2	1.480 (6)	C3—H3	0.955
C1—C9	1.451 (5)	C4—H4	0.957
C2—C3	1.468 (6)	C5—H5	0.949
C3—C4	1.325 (5)	C6—H6	0.948
C4—C10	1.447 (6)	C7—H7	0.945
C5—C6	1.383 (6)	C8—H8	0.947
C5—C10	1.406 (6)	C13—H13	0.953
C6—C7	1.414 (6)	C14—H14	0.952
C7—C8	1.390 (5)	C15—H15	0.955
C8—C9	1.402 (6)	C16—H16	0.951
C9—C10	1.412 (6)
N2—N1—C11	113.9 (5)	N3—C12—C13	116.5 (4)
N1—N2—C1	111.8 (5)	C12—C13—C14	120.3 (4)
O2—N3—O3	121.8 (5)	C13—C14—C15	119.6 (4)
O3—N3—C12	118.2 (4)	C14—C15—C16	121.0 (4)
O2—N3—C12	120.0 (4)	C11—C16—C15	119.9 (4)
N2—C1—C9	112.8 (4)	C11—N1—H1	122.5
N2—C1—C2	129.4 (5)	N2—N1—H1	123.2
C2—C1—C9	117.8 (3)	C2—C3—H3	112.9
O1—C2—C1	117.4 (4)	C4—C3—H3	125.6
C1—C2—C3	119.1 (4)	C3—C4—H4	125.4
O1—C2—C3	123.5 (4)	C10—C4—H4	114.3
C2—C3—C4	121.5 (4)	C10—C5—H5	118.9
C3—C4—C10	120.4 (4)	C6—C5—H5	121.1
C6—C5—C10	120.1 (4)	C7—C6—H6	118.5
C5—C6—C7	120.2 (4)	C5—C6—H6	121.3
C6—C7—C8	120.4 (4)	C8—C7—H7	121.0
C7—C8—C9	119.3 (4)	C6—C7—H7	118.6
C1—C9—C8	120.6 (4)	C7—C8—H8	121.1
C8—C9—C10	120.5 (4)	C9—C8—H8	119.6
C1—C9—C10	118.9 (4)	C12—C13—H13	118.5
C5—C10—C9	119.5 (4)	C14—C13—H13	121.1
C4—C10—C9	122.3 (4)	C13—C14—H14	121.2
C4—C10—C5	118.3 (4)	C15—C14—H14	119.2
N1—C11—C16	121.4 (4)	C14—C15—H15	118.5
N1—C11—C12	119.6 (5)	C16—C15—H15	120.4
C12—C11—C16	119.0 (4)	C15—C16—H16	121.6
N3—C12—C11	123.5 (4)	C11—C16—H16	118.5
C11—C12—C13	120.1 (4)