1-[(Phenyl-iminio)amino]-2-naphtho-late.

In the zwitterionic title compound, C(16)H(12)N(2)O, the dihedral angle between the benzene ring and naphthalene ring system is 2.0 (1)°. The azo group adopts a trans configuration and an intra-molecular N-H⋯O hydrogen bond is found. In the crystal, the mol-ecules are packed by strong π-π inter-actions [centroid-centroid distance between aromatic rings = 3.375 (3) Å].

Related literature

For general background to the use of azo compounds as dyes, pigments and advanced materials, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶). Many azo compounds have been synthesized by diazo­tization and diazo coupling reactions, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C16H12N2O

M = 248.28

Monoclinic,

a = 27.8713 (4) Å

b = 6.0248 (1) Å

c = 14.9199 (2) Å

β = 103.570 (2)°

V = 2435.40 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.989, T max = 0.993

8859 measured reflections

3002 independent reflections

2536 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.169

S = 1.08

3002 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023329/rk2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023329/rk2210Isup2.hkl

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

C16H12N2O	F(000) = 1040
Mr = 248.28	Dx = 1.354 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2783 reflections
a = 27.8713 (4) Å	θ = 2.8–28.2°
b = 6.0248 (1) Å	µ = 0.09 mm−1
c = 14.9199 (2) Å	T = 200 K
β = 103.570 (2)°	Block, red
V = 2435.40 (7) Å3	0.13 × 0.10 × 0.08 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	3002 independent reflections
Radiation source: fine–focus sealed tube	2536 reflections with I > 2σ(I)
graphite	Rint = 0.088
φ and ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −35→36
Tmin = 0.989, Tmax = 0.993	k = −8→8
8859 measured reflections	l = −15→19

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0799P)2 + 1.0846P] where P = (Fo2 + 2Fc2)/3
3002 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R–factors(gt) 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
C1	0.14696 (5)	0.0629 (2)	0.09018 (10)	0.0244 (3)
C2	0.19947 (5)	0.0124 (3)	0.11604 (10)	0.0287 (3)
C3	0.21439 (6)	−0.1846 (3)	0.17062 (11)	0.0330 (4)
H3	0.2485	−0.2197	0.1901	0.040*
C4	0.18102 (6)	−0.3195 (3)	0.19449 (11)	0.0319 (4)
H4	0.1924	−0.4484	0.2298	0.038*
C5	0.12895 (5)	−0.2771 (2)	0.16900 (10)	0.0256 (3)
C6	0.09522 (6)	−0.4260 (3)	0.19251 (11)	0.0314 (4)
H6	0.1070	−0.5575	0.2256	0.038*
C7	0.04557 (6)	−0.3840 (3)	0.16840 (11)	0.0337 (4)
H7	0.0230	−0.4870	0.1839	0.040*
C8	0.02823 (6)	−0.1896 (3)	0.12098 (11)	0.0324 (4)
H8	−0.0062	−0.1594	0.1052	0.039*
C9	0.06067 (5)	−0.0409 (2)	0.09676 (10)	0.0282 (3)
H9	0.0484	0.0912	0.0648	0.034*
C10	0.11155 (5)	−0.0826 (2)	0.11877 (9)	0.0237 (3)
C11	0.13828 (6)	0.5505 (2)	−0.04777 (9)	0.0255 (3)
C12	0.17170 (6)	0.6926 (3)	−0.07488 (11)	0.0311 (4)
H12	0.2061	0.6623	−0.0576	0.037*
C13	0.15433 (7)	0.8788 (3)	−0.12732 (11)	0.0355 (4)
H13	0.1769	0.9765	−0.1460	0.043*
C14	0.10432 (6)	0.9226 (3)	−0.15249 (11)	0.0340 (4)
H14	0.0925	1.0507	−0.1879	0.041*
C15	0.07150 (6)	0.7790 (3)	−0.12588 (11)	0.0329 (4)
H15	0.0371	0.8088	−0.1438	0.039*
C16	0.08806 (6)	0.5922 (2)	−0.07338 (11)	0.0292 (3)
H16	0.0653	0.4944	−0.0553	0.035*
N1	0.12797 (5)	0.23592 (19)	0.03768 (8)	0.0253 (3)
N2	0.15775 (5)	0.3675 (2)	0.00730 (9)	0.0268 (3)
H2A	0.1899 (7)	0.333 (3)	0.0227 (13)	0.032*
O1	0.23107 (4)	0.1341 (2)	0.09144 (9)	0.0387 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0285 (7)	0.0253 (7)	0.0190 (7)	0.0024 (5)	0.0050 (5)	−0.0008 (5)
C2	0.0281 (7)	0.0323 (8)	0.0243 (7)	0.0009 (6)	0.0030 (6)	−0.0012 (6)
C3	0.0263 (7)	0.0406 (9)	0.0288 (8)	0.0067 (6)	−0.0003 (6)	0.0043 (7)
C4	0.0357 (8)	0.0321 (8)	0.0255 (8)	0.0084 (6)	0.0020 (6)	0.0068 (6)
C5	0.0327 (8)	0.0274 (7)	0.0166 (7)	0.0027 (6)	0.0058 (6)	−0.0008 (5)
C6	0.0416 (9)	0.0292 (7)	0.0250 (8)	0.0036 (6)	0.0110 (6)	0.0037 (6)
C7	0.0381 (9)	0.0335 (8)	0.0329 (9)	−0.0032 (6)	0.0151 (7)	0.0020 (6)
C8	0.0292 (8)	0.0388 (9)	0.0306 (8)	0.0029 (6)	0.0097 (6)	0.0001 (6)
C9	0.0300 (7)	0.0307 (7)	0.0241 (7)	0.0059 (6)	0.0069 (6)	0.0034 (6)
C10	0.0292 (7)	0.0258 (7)	0.0163 (6)	0.0032 (5)	0.0059 (5)	−0.0013 (5)
C11	0.0351 (8)	0.0239 (7)	0.0184 (7)	0.0026 (6)	0.0080 (6)	−0.0009 (5)
C12	0.0343 (8)	0.0324 (8)	0.0284 (8)	0.0010 (6)	0.0113 (6)	0.0007 (6)
C13	0.0489 (10)	0.0314 (8)	0.0304 (8)	−0.0022 (7)	0.0180 (7)	0.0031 (6)
C14	0.0521 (10)	0.0271 (7)	0.0232 (8)	0.0076 (7)	0.0100 (7)	0.0030 (6)
C15	0.0387 (8)	0.0315 (8)	0.0274 (8)	0.0071 (6)	0.0057 (7)	−0.0008 (6)
C16	0.0340 (8)	0.0273 (7)	0.0276 (8)	0.0001 (6)	0.0101 (6)	0.0001 (6)
N1	0.0317 (7)	0.0257 (6)	0.0192 (6)	0.0011 (5)	0.0073 (5)	−0.0017 (4)
N2	0.0284 (6)	0.0271 (6)	0.0253 (7)	0.0019 (5)	0.0071 (5)	0.0023 (5)
O1	0.0284 (6)	0.0426 (7)	0.0437 (7)	−0.0017 (5)	0.0058 (5)	0.0084 (5)

C1—N1	1.3364 (18)	C9—C10	1.401 (2)
C1—C2	1.455 (2)	C9—H9	0.9500
C1—C10	1.457 (2)	C11—C16	1.385 (2)
C2—O1	1.2650 (18)	C11—C12	1.393 (2)
C2—C3	1.444 (2)	C11—N2	1.4058 (18)
C3—C4	1.344 (2)	C12—C13	1.389 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.434 (2)	C13—C14	1.381 (2)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.402 (2)	C14—C15	1.383 (2)
C5—C10	1.4141 (19)	C14—H14	0.9500
C6—C7	1.369 (2)	C15—C16	1.387 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.395 (2)	C16—H16	0.9500
C7—H7	0.9500	N1—N2	1.3033 (17)
C8—C9	1.380 (2)	N2—H2A	0.895 (19)
C8—H8	0.9500
N1—C1—C2	123.63 (13)	C10—C9—H9	119.6
N1—C1—C10	116.02 (13)	C9—C10—C5	118.37 (13)
C2—C1—C10	120.32 (13)	C9—C10—C1	122.79 (13)
O1—C2—C3	120.81 (14)	C5—C10—C1	118.82 (13)
O1—C2—C1	121.82 (13)	C16—C11—C12	120.65 (13)
C3—C2—C1	117.37 (13)	C16—C11—N2	122.01 (13)
C4—C3—C2	121.37 (14)	C12—C11—N2	117.33 (14)
C4—C3—H3	119.3	C13—C12—C11	119.46 (15)
C2—C3—H3	119.3	C13—C12—H12	120.3
C3—C4—C5	122.82 (14)	C11—C12—H12	120.3
C3—C4—H4	118.6	C14—C13—C12	120.23 (15)
C5—C4—H4	118.6	C14—C13—H13	119.9
C6—C5—C10	119.73 (14)	C12—C13—H13	119.9
C6—C5—C4	121.06 (13)	C13—C14—C15	119.73 (14)
C10—C5—C4	119.21 (13)	C13—C14—H14	120.1
C7—C6—C5	120.78 (14)	C15—C14—H14	120.1
C7—C6—H6	119.6	C14—C15—C16	120.98 (15)
C5—C6—H6	119.6	C14—C15—H15	119.5
C6—C7—C8	119.79 (14)	C16—C15—H15	119.5
C6—C7—H7	120.1	C11—C16—C15	118.95 (14)
C8—C7—H7	120.1	C11—C16—H16	120.5
C9—C8—C7	120.52 (14)	C15—C16—H16	120.5
C9—C8—H8	119.7	N2—N1—C1	118.77 (12)
C7—C8—H8	119.7	N1—N2—C11	119.36 (13)
C8—C9—C10	120.77 (14)	N1—N2—H2A	116.7 (11)
C8—C9—H9	119.6	C11—N2—H2A	123.9 (11)
N1—C1—C2—O1	1.5 (2)	C4—C5—C10—C1	3.3 (2)
C10—C1—C2—O1	179.23 (13)	N1—C1—C10—C9	−2.8 (2)
N1—C1—C2—C3	−177.99 (13)	C2—C1—C10—C9	179.28 (13)
C10—C1—C2—C3	−0.2 (2)	N1—C1—C10—C5	175.65 (12)
O1—C2—C3—C4	−177.66 (15)	C2—C1—C10—C5	−2.3 (2)
C1—C2—C3—C4	1.8 (2)	C16—C11—C12—C13	0.6 (2)
C2—C3—C4—C5	−0.8 (2)	N2—C11—C12—C13	−178.35 (13)
C3—C4—C5—C6	177.74 (15)	C11—C12—C13—C14	−0.1 (2)
C3—C4—C5—C10	−1.8 (2)	C12—C13—C14—C15	−0.5 (2)
C10—C5—C6—C7	−0.8 (2)	C13—C14—C15—C16	0.6 (2)
C4—C5—C6—C7	179.65 (15)	C12—C11—C16—C15	−0.6 (2)
C5—C6—C7—C8	−0.9 (2)	N2—C11—C16—C15	178.39 (13)
C6—C7—C8—C9	1.1 (2)	C14—C15—C16—C11	−0.1 (2)
C7—C8—C9—C10	0.4 (2)	C2—C1—N1—N2	0.2 (2)
C8—C9—C10—C5	−2.0 (2)	C10—C1—N1—N2	−177.61 (12)
C8—C9—C10—C1	176.43 (13)	C1—N1—N2—C11	−179.81 (12)
C6—C5—C10—C9	2.2 (2)	C16—C11—N2—N1	−2.1 (2)
C4—C5—C10—C9	−178.23 (13)	C12—C11—N2—N1	176.92 (12)
C6—C5—C10—C1	−176.27 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.895 (19)	1.803 (18)	2.5545 (17)	140.0 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.895 (19)	1.803 (18)	2.5545 (17)	140.0 (16)