(E)-1-(2-Phenyl-diazen-2-ium-1-yl)naph-thalen-2-olate.

In the title zwitterionic compound, C16H12N2O, the dihedral angle between the phenyl ring and the naphthalene ring system is 17.85 (8)°; an intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, π-π stacking is observed between naphthalene ring systems of adjacent mol-ecules, the centroid-centroid distance being 3.6486 (11) Å.

Related literature

For general background to azo compounds and their applications in the fields of dyes, pigments and advanced materials, see: Biswas & Umapathy (2000 ▶); Willner & Rubin (1996 ▶); Hunger (2003 ▶); Catino & Farris (1985 ▶); Zollinger (2003 ▶); Bahatti & Seshadri (2004 ▶); Taniike et al. (1996 ▶); Fadda et al. (1994 ▶); Bach et al. (1996 ▶); Clark & Hester (1993 ▶). For the synthesis, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C16H12N2O

M = 248.28

Monoclinic,

a = 13.0800 (12) Å

b = 13.5170 (13) Å

c = 7.0080 (4) Å

β = 94.140 (6)°

V = 1235.80 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.26 × 0.22 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer

4092 measured reflections

2139 independent reflections

1546 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.144

S = 1.06

2139 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1999 ▶); cell refinement: KappaCCD Server Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813020102/xu5718sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020102/xu5718Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020102/xu5718Isup3.cml

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

C16H12N2O	F(000) = 520
Mr = 248.28	Dx = 1.334 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2200 reflections
a = 13.0800 (12) Å	θ = 1.0–25.4°
b = 13.5170 (13) Å	µ = 0.09 mm−1
c = 7.0080 (4) Å	T = 150 K
β = 94.140 (6)°	Prism, red
V = 1235.80 (18) Å3	0.26 × 0.22 × 0.17 mm
Z = 4

Nonius KappaCCD diffractometer	1546 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 25.4°, θmin = 2.2°
Detector resolution: 9 pixels mm-1	h = −15→15
CCD scans	k = −16→16
4092 measured reflections	l = −7→7
2139 independent reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0756P)2 + 0.113P] where P = (Fo2 + 2Fc2)/3
2139 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except those 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
N1	0.20061 (11)	0.46423 (10)	0.4042 (2)	0.0542 (4)
H1	0.1287	0.4666	0.4047	0.065*
N2	0.23990 (12)	0.37596 (10)	0.4036 (2)	0.0524 (4)
O1	0.02112 (10)	0.39323 (10)	0.3599 (2)	0.0688 (4)
C1	0.26520 (14)	0.54729 (12)	0.4226 (2)	0.0510 (4)
C2	0.36888 (15)	0.54252 (15)	0.3965 (3)	0.0630 (5)
H2	0.3987	0.4832	0.3627	0.076*
C3	0.42736 (16)	0.62723 (15)	0.4215 (3)	0.0700 (6)
H3	0.4972	0.6246	0.4052	0.084*
C4	0.38374 (17)	0.71530 (16)	0.4701 (3)	0.0727 (6)
H4	0.4240	0.7718	0.4868	0.087*
C5	0.28076 (17)	0.71967 (15)	0.4938 (3)	0.0718 (6)
H5	0.2511	0.7792	0.5267	0.086*
C6	0.22090 (15)	0.63589 (13)	0.4690 (3)	0.0603 (5)
H6	0.1509	0.6392	0.4836	0.072*
C7	0.17482 (13)	0.29843 (12)	0.3881 (2)	0.0490 (4)
C8	0.06510 (15)	0.30859 (14)	0.3645 (3)	0.0563 (5)
C9	0.00491 (15)	0.22000 (16)	0.3455 (3)	0.0651 (5)
H9	−0.0660	0.2249	0.3272	0.078*
C10	0.04871 (16)	0.12996 (15)	0.3537 (3)	0.0634 (5)
H10	0.0069	0.0744	0.3419	0.076*
C11	0.15749 (15)	0.11656 (13)	0.3798 (2)	0.0543 (5)
C12	0.22131 (14)	0.20077 (12)	0.3962 (2)	0.0509 (4)
C13	0.32739 (15)	0.18637 (15)	0.4207 (3)	0.0635 (5)
H13	0.3709	0.2408	0.4328	0.076*
C14	0.36788 (17)	0.09244 (15)	0.4270 (3)	0.0728 (6)
H14	0.4385	0.0840	0.4437	0.087*
C15	0.30467 (18)	0.01006 (16)	0.4088 (3)	0.0723 (6)
H15	0.3329	−0.0531	0.4119	0.087*
C16	0.20132 (17)	0.02215 (14)	0.3865 (3)	0.0647 (5)
H16	0.1591	−0.0332	0.3755	0.078*

	U11	U22	U33	U12	U13	U23
N1	0.0545 (9)	0.0442 (9)	0.0639 (10)	0.0000 (7)	0.0040 (7)	0.0008 (6)
N2	0.0613 (9)	0.0424 (9)	0.0534 (9)	0.0008 (7)	0.0040 (6)	−0.0001 (6)
O1	0.0601 (8)	0.0556 (9)	0.0902 (10)	0.0066 (7)	0.0019 (7)	−0.0011 (7)
C1	0.0580 (10)	0.0412 (10)	0.0534 (10)	−0.0017 (8)	0.0010 (8)	0.0031 (7)
C2	0.0625 (12)	0.0510 (12)	0.0760 (13)	0.0055 (9)	0.0072 (9)	−0.0013 (9)
C3	0.0567 (11)	0.0630 (14)	0.0899 (15)	−0.0042 (10)	0.0027 (10)	0.0022 (10)
C4	0.0723 (14)	0.0514 (12)	0.0939 (16)	−0.0106 (11)	0.0019 (11)	−0.0008 (10)
C5	0.0777 (14)	0.0455 (11)	0.0925 (16)	0.0029 (10)	0.0086 (11)	−0.0029 (10)
C6	0.0580 (11)	0.0488 (11)	0.0743 (13)	0.0035 (9)	0.0071 (9)	0.0036 (9)
C7	0.0558 (10)	0.0446 (10)	0.0466 (10)	−0.0025 (8)	0.0039 (7)	−0.0027 (7)
C8	0.0641 (12)	0.0525 (11)	0.0523 (11)	−0.0002 (9)	0.0044 (8)	−0.0025 (8)
C9	0.0586 (11)	0.0626 (13)	0.0739 (13)	−0.0071 (10)	0.0031 (9)	−0.0106 (9)
C10	0.0699 (13)	0.0528 (12)	0.0679 (12)	−0.0153 (10)	0.0065 (9)	−0.0085 (9)
C11	0.0702 (12)	0.0464 (11)	0.0467 (10)	−0.0040 (9)	0.0061 (8)	−0.0048 (7)
C12	0.0628 (11)	0.0451 (10)	0.0450 (10)	−0.0017 (8)	0.0059 (7)	−0.0012 (7)
C13	0.0623 (12)	0.0501 (12)	0.0780 (13)	−0.0001 (9)	0.0039 (10)	0.0015 (9)
C14	0.0701 (13)	0.0554 (13)	0.0928 (16)	0.0097 (11)	0.0050 (11)	0.0043 (11)
C15	0.0933 (16)	0.0450 (12)	0.0788 (14)	0.0100 (11)	0.0081 (11)	0.0016 (9)
C16	0.0843 (14)	0.0447 (11)	0.0654 (12)	−0.0052 (10)	0.0079 (10)	−0.0032 (8)

N1—N2	1.2993 (19)	C7—C12	1.453 (2)
N1—C1	1.405 (2)	C8—C9	1.434 (3)
N1—H1	0.9418	C9—C10	1.345 (3)
N2—C7	1.350 (2)	C9—H9	0.9300
O1—C8	1.280 (2)	C10—C11	1.433 (3)
C1—C6	1.380 (2)	C10—H10	0.9300
C1—C2	1.383 (3)	C11—C16	1.398 (3)
C2—C3	1.381 (3)	C11—C12	1.411 (2)
C2—H2	0.9300	C12—C13	1.399 (3)
C3—C4	1.374 (3)	C13—C14	1.375 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.370 (3)	C14—C15	1.387 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.381 (3)	C15—C16	1.359 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.439 (3)
N2—N1—C1	119.91 (15)	O1—C8—C7	122.06 (16)
N2—N1—H1	115.2	C9—C8—C7	117.85 (17)
C1—N1—H1	124.6	C10—C9—C8	121.51 (18)
N1—N2—C7	117.78 (15)	C10—C9—H9	119.2
C6—C1—C2	120.28 (17)	C8—C9—H9	119.2
C6—C1—N1	117.08 (16)	C9—C10—C11	122.41 (18)
C2—C1—N1	122.64 (16)	C9—C10—H10	118.8
C3—C2—C1	118.96 (18)	C11—C10—H10	118.8
C3—C2—H2	120.5	C16—C11—C12	119.65 (18)
C1—C2—H2	120.5	C16—C11—C10	121.37 (17)
C4—C3—C2	120.9 (2)	C12—C11—C10	118.98 (16)
C4—C3—H3	119.5	C13—C12—C11	118.24 (16)
C2—C3—H3	119.5	C13—C12—C7	122.67 (16)
C5—C4—C3	119.80 (19)	C11—C12—C7	119.09 (17)
C5—C4—H4	120.1	C14—C13—C12	120.57 (18)
C3—C4—H4	120.1	C14—C13—H13	119.7
C4—C5—C6	120.19 (19)	C12—C13—H13	119.7
C4—C5—H5	119.9	C13—C14—C15	120.8 (2)
C6—C5—H5	119.9	C13—C14—H14	119.6
C1—C6—C5	119.85 (18)	C15—C14—H14	119.6
C1—C6—H6	120.1	C16—C15—C14	119.7 (2)
C5—C6—H6	120.1	C16—C15—H15	120.2
N2—C7—C8	123.58 (16)	C14—C15—H15	120.2
N2—C7—C12	116.27 (16)	C15—C16—C11	121.02 (19)
C8—C7—C12	120.16 (16)	C15—C16—H16	119.5
O1—C8—C9	120.09 (18)	C11—C16—H16	119.5
C1—N1—N2—C7	179.15 (14)	C8—C9—C10—C11	−0.6 (3)
N2—N1—C1—C6	−164.58 (16)	C9—C10—C11—C16	−179.56 (17)
N2—N1—C1—C2	15.3 (2)	C9—C10—C11—C12	−0.5 (3)
C6—C1—C2—C3	1.3 (3)	C16—C11—C12—C13	−0.6 (2)
N1—C1—C2—C3	−178.58 (17)	C10—C11—C12—C13	−179.67 (16)
C1—C2—C3—C4	−0.5 (3)	C16—C11—C12—C7	179.69 (14)
C2—C3—C4—C5	−0.2 (3)	C10—C11—C12—C7	0.6 (2)
C3—C4—C5—C6	0.0 (3)	N2—C7—C12—C13	0.7 (2)
C2—C1—C6—C5	−1.5 (3)	C8—C7—C12—C13	−179.37 (16)
N1—C1—C6—C5	178.41 (17)	N2—C7—C12—C11	−179.68 (14)
C4—C5—C6—C1	0.8 (3)	C8—C7—C12—C11	0.3 (2)
N1—N2—C7—C8	2.6 (2)	C11—C12—C13—C14	0.5 (3)
N1—N2—C7—C12	−177.42 (13)	C7—C12—C13—C14	−179.82 (17)
N2—C7—C8—O1	−1.2 (3)	C12—C13—C14—C15	0.1 (3)
C12—C7—C8—O1	178.80 (15)	C13—C14—C15—C16	−0.7 (3)
N2—C7—C8—C9	178.63 (15)	C14—C15—C16—C11	0.6 (3)
C12—C7—C8—C9	−1.3 (2)	C12—C11—C16—C15	0.1 (3)
O1—C8—C9—C10	−178.64 (17)	C10—C11—C16—C15	179.11 (18)
C7—C8—C9—C10	1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.94	1.73	2.5346 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.94	1.73	2.5346 (19)	141