1-Diazo-naphthalen-2(1H)-one.

The mol-ecule of the title compound, C(10)H(6)N(2)O, is nearly planar [maximum deviation = 0.030 (1) Å]. The CN(2) moiety is almost linear, with a C-N-N angle of 175.50 (14)°. A single inter-molecular C-H⋯O hydrogen bond is observed in the crystal structure. A π-π inter-action is also observed with the shortest distance being 3.6832 (12) Å between the the centroids of the six-membered rings.

Related literature

For the synthesis, see: Kitamura et al. (2010 ▶). For the crystal structure of related diazo­naphtho­quinones, see: Seidel et al. (1989 ▶); Ferreira et al. (2006 ▶). For an example of the utility of the diazo­naphtho­quinones, see Reiser et al. (1996 ▶).

Experimental

Crystal data

C10H6N2O

M = 170.17

Orthorhombic,

a = 11.900 (2) Å

b = 9.1978 (15) Å

c = 14.521 (3) Å

V = 1589.4 (5) Å3

Z = 8

Cu Kα radiation

μ = 0.78 mm−1

T = 123 K

0.50 × 0.40 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.566, T max = 0.731

18038 measured reflections

1456 independent reflections

1359 reflections with F 2 > 2σ(F 2)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.08

1456 reflections

119 parameters

All H-atom parameters refined

Δρmax = 0.29 e Å−3

Δρmin = −0.13 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku Americas and Rigaku, 2007 ▶); program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: CrystalStructure and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026377/pv2420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026377/pv2420Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026377/pv2420Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H6N2O	F(000) = 704.00
Mr = 170.17	Dx = 1.422 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17442 reflections
a = 11.900 (2) Å	θ = 3.0–68.2°
b = 9.1978 (15) Å	µ = 0.78 mm−1
c = 14.521 (3) Å	T = 123 K
V = 1589.4 (5) Å3	Prism, brown
Z = 8	0.50 × 0.40 × 0.40 mm

Rigaku R-AXIS RAPID diffractometer	1359 reflections with F2 > 2σ(F2)
Detector resolution: 5.00 pixels mm-1	Rint = 0.018
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.566, Tmax = 0.731	k = −10→10
18038 measured reflections	l = −17→17
1456 independent reflections

Refinement on F2	0 restraints
R[F2 > 2σ(F2)] = 0.044	All H-atom parameters refined
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.5878P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1456 reflections	Δρmax = 0.29 e Å−3
119 parameters	Δρmin = −0.13 e Å−3

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 mat- rix. 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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O(1)	0.41204 (11)	1.07612 (13)	0.22608 (7)	0.0476 (3)
N(1)	0.55271 (11)	0.89513 (13)	0.31064 (8)	0.0327 (3)
N(2)	0.63438 (13)	0.87983 (16)	0.27341 (9)	0.0441 (3)
C(1)	0.45523 (13)	0.92398 (16)	0.35238 (10)	0.0336 (3)
C(2)	0.38659 (14)	1.02931 (17)	0.30396 (11)	0.0390 (4)
C(3)	0.28687 (14)	1.07339 (17)	0.35513 (11)	0.0406 (4)
C(4)	0.26340 (13)	1.01769 (18)	0.43965 (12)	0.0419 (4)
C(5)	0.33263 (12)	0.91102 (16)	0.48560 (10)	0.0344 (3)
C(6)	0.30613 (13)	0.85591 (18)	0.57389 (11)	0.0389 (4)
C(7)	0.37387 (14)	0.75293 (19)	0.61482 (11)	0.0395 (4)
C(8)	0.46903 (13)	0.70173 (19)	0.56895 (11)	0.0388 (4)
C(9)	0.49762 (13)	0.75479 (17)	0.48334 (10)	0.0343 (3)
C(10)	0.43117 (12)	0.85986 (16)	0.44128 (10)	0.0310 (3)
H(1)	0.2371	1.1427	0.3288	0.049*
H(2)	0.1977	1.0508	0.4703	0.050*
H(3)	0.2412	0.8901	0.6052	0.047*
H(4)	0.3558	0.7168	0.6743	0.047*
H(5)	0.5146	0.6295	0.5971	0.047*
H(6)	0.5629	0.7195	0.4530	0.041*

	U11	U22	U33	U12	U13	U23
O(1)	0.0703 (8)	0.0379 (6)	0.0347 (6)	0.0036 (5)	−0.0079 (5)	0.0033 (4)
N(1)	0.0406 (7)	0.0295 (6)	0.0279 (6)	−0.0016 (5)	0.0014 (5)	0.0001 (4)
N(2)	0.0509 (8)	0.0411 (8)	0.0403 (7)	−0.0027 (6)	0.0117 (6)	0.0025 (6)
C(1)	0.0362 (8)	0.0325 (7)	0.0320 (7)	−0.0001 (6)	−0.0012 (6)	−0.0042 (5)
C(2)	0.0501 (9)	0.0313 (8)	0.0355 (8)	−0.0008 (6)	−0.0102 (7)	−0.0042 (6)
C(3)	0.0414 (8)	0.0361 (8)	0.0442 (9)	0.0067 (6)	−0.0124 (7)	−0.0073 (6)
C(4)	0.0327 (7)	0.0423 (8)	0.0506 (9)	0.0021 (6)	−0.0036 (6)	−0.0167 (7)
C(5)	0.0317 (7)	0.0345 (8)	0.0371 (8)	−0.0045 (6)	−0.0059 (6)	−0.0105 (6)
C(6)	0.0305 (7)	0.0483 (9)	0.0379 (8)	−0.0096 (6)	0.0041 (6)	−0.0150 (7)
C(7)	0.0428 (8)	0.0484 (9)	0.0274 (7)	−0.0132 (7)	0.0011 (6)	−0.0029 (6)
C(8)	0.0388 (8)	0.0428 (9)	0.0349 (8)	−0.0056 (6)	−0.0043 (6)	0.0004 (6)
C(9)	0.0300 (6)	0.0384 (8)	0.0344 (8)	−0.0019 (6)	−0.0001 (6)	−0.0027 (6)
C(10)	0.0308 (7)	0.0336 (7)	0.0288 (7)	−0.0074 (5)	−0.0015 (5)	−0.0071 (5)

O(1)—C(2)	1.2474 (19)	C(6)—C(7)	1.378 (2)
N(1)—N(2)	1.1210 (19)	C(7)—C(8)	1.396 (2)
N(1)—C(1)	1.3355 (19)	C(8)—C(9)	1.378 (2)
C(1)—C(2)	1.449 (2)	C(9)—C(10)	1.390 (2)
C(1)—C(10)	1.448 (2)	C(3)—H(1)	0.950
C(2)—C(3)	1.458 (2)	C(4)—H(2)	0.950
C(3)—C(4)	1.359 (2)	C(6)—H(3)	0.950
C(4)—C(5)	1.444 (2)	C(7)—H(4)	0.950
C(5)—C(6)	1.414 (2)	C(8)—H(5)	0.950
C(5)—C(10)	1.418 (2)	C(9)—H(6)	0.950
N(2)—N(1)—C(1)	175.50 (14)	C(1)—C(10)—C(5)	115.66 (12)
N(1)—C(1)—C(2)	113.72 (13)	C(1)—C(10)—C(9)	124.23 (13)
N(1)—C(1)—C(10)	119.70 (13)	C(5)—C(10)—C(9)	120.11 (13)
C(2)—C(1)—C(10)	126.40 (13)	C(2)—C(3)—H(1)	119.2
O(1)—C(2)—C(1)	122.26 (14)	C(4)—C(3)—H(1)	119.2
O(1)—C(2)—C(3)	124.32 (14)	C(3)—C(4)—H(2)	118.1
C(1)—C(2)—C(3)	113.42 (13)	C(5)—C(4)—H(2)	118.1
C(2)—C(3)—C(4)	121.52 (14)	C(5)—C(6)—H(3)	119.8
C(3)—C(4)—C(5)	123.78 (14)	C(7)—C(6)—H(3)	119.8
C(4)—C(5)—C(6)	122.35 (13)	C(6)—C(7)—H(4)	120.0
C(4)—C(5)—C(10)	119.17 (13)	C(8)—C(7)—H(4)	120.0
C(6)—C(5)—C(10)	118.48 (13)	C(7)—C(8)—H(5)	119.6
C(5)—C(6)—C(7)	120.45 (14)	C(9)—C(8)—H(5)	119.6
C(6)—C(7)—C(8)	120.04 (14)	C(8)—C(9)—H(6)	119.9
C(7)—C(8)—C(9)	120.75 (15)	C(10)—C(9)—H(6)	119.9
C(8)—C(9)—C(10)	120.14 (14)
N(2)—N(1)—C(1)—C(2)	29.7 (19)	C(3)—C(4)—C(5)—C(6)	179.60 (15)
N(2)—N(1)—C(1)—C(10)	−145.8 (18)	C(3)—C(4)—C(5)—C(10)	−0.0 (2)
N(1)—C(1)—C(2)—O(1)	7.0 (2)	C(4)—C(5)—C(6)—C(7)	179.26 (15)
N(1)—C(1)—C(2)—C(3)	−173.04 (13)	C(4)—C(5)—C(10)—C(1)	1.5 (2)
N(1)—C(1)—C(10)—C(5)	172.20 (13)	C(4)—C(5)—C(10)—C(9)	−178.53 (14)
N(1)—C(1)—C(10)—C(9)	−7.8 (2)	C(6)—C(5)—C(10)—C(1)	−178.15 (13)
C(2)—C(1)—C(10)—C(5)	−2.6 (2)	C(6)—C(5)—C(10)—C(9)	1.8 (2)
C(2)—C(1)—C(10)—C(9)	177.38 (15)	C(10)—C(5)—C(6)—C(7)	−1.1 (2)
C(10)—C(1)—C(2)—O(1)	−177.92 (14)	C(5)—C(6)—C(7)—C(8)	−0.3 (2)
C(10)—C(1)—C(2)—C(3)	2.1 (2)	C(6)—C(7)—C(8)—C(9)	1.1 (2)
O(1)—C(2)—C(3)—C(4)	179.61 (15)	C(7)—C(8)—C(9)—C(10)	−0.4 (2)
C(1)—C(2)—C(3)—C(4)	−0.4 (2)	C(8)—C(9)—C(10)—C(1)	178.89 (14)
C(2)—C(3)—C(4)—C(5)	−0.6 (2)	C(8)—C(9)—C(10)—C(5)	−1.1 (2)

D—H···A

—···

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H3⋯O1i	0.95	2.55	3.466 (2)	162

Symmetry code: (i) .