1-(4-Cyano-phenyl-diazen-2-ium-1-yl)-2-naphtholate.

In the mol-ecule of the zwitterionic title compound, C(17)H(11)N(3)O, the naphthalene ring system is planar [maximum deviation = 0.029 (3) Å] and is oriented at a dihedral angle of 3.55 (3)° with respect to the benzene ring. An intra-molecular N-H⋯O hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into centrosymmetric dimers.

Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶). For a related structure, see: Rădulescu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H11N3O

M = 273.29

Monoclinic,

a = 5.2673 (11) Å

b = 9.910 (2) Å

c = 25.239 (6) Å

β = 96.13 (3)°

V = 1309.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.35 × 0.10 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.973, T max = 0.979

13086 measured reflections

2998 independent reflections

1941 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.148

S = 1.02

2998 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028438/hk2742sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028438/hk2742Isup2.hkl

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

C17H11N3O	F(000) = 568
Mr = 273.29	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1658 reflections
a = 5.2673 (11) Å	θ = 3.2–28.9°
b = 9.910 (2) Å	µ = 0.09 mm−1
c = 25.239 (6) Å	T = 294 K
β = 96.13 (3)°	Block, red
V = 1309.9 (5) Å3	0.35 × 0.10 × 0.10 mm
Z = 4

Rigaku SCXmini diffractometer	2998 independent reflections
Radiation source: fine-focus sealed tube	1941 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.973, Tmax = 0.979	l = −32→32
13086 measured 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) = 0.148	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0717P)2 + 0.0861P] where P = (Fo2 + 2Fc2)/3
2998 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.25 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 matrix. 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 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
O1	0.2630 (3)	−0.03169 (14)	0.45197 (5)	0.0627 (4)
N1	0.3499 (3)	0.15188 (14)	0.36889 (6)	0.0424 (4)
N2	0.5123 (3)	0.16008 (14)	0.41170 (5)	0.0444 (4)
H2A	0.4994	0.1072	0.4383	0.053*
N3	1.4464 (4)	0.62761 (18)	0.42541 (8)	0.0731 (5)
C1	0.1628 (3)	0.06230 (17)	0.36607 (7)	0.0427 (4)
C2	0.1200 (4)	−0.03101 (18)	0.40895 (7)	0.0503 (5)
C3	−0.0963 (4)	−0.12070 (19)	0.39970 (8)	0.0576 (5)
H3A	−0.1284	−0.1821	0.4261	0.069*
C4	−0.2519 (4)	−0.11777 (18)	0.35418 (8)	0.0542 (5)
H4A	−0.3884	−0.1777	0.3501	0.065*
C5	−0.2179 (3)	−0.02633 (17)	0.31131 (7)	0.0456 (4)
C6	−0.3895 (3)	−0.02176 (19)	0.26515 (7)	0.0534 (5)
H6A	−0.5266	−0.0814	0.2614	0.064*
C7	−0.3597 (4)	0.0688 (2)	0.22535 (7)	0.0554 (5)
H7A	−0.4760	0.0711	0.1949	0.066*
C8	−0.1543 (4)	0.15722 (19)	0.23078 (7)	0.0514 (5)
H8A	−0.1329	0.2185	0.2037	0.062*
C9	0.0175 (3)	0.15515 (18)	0.27562 (7)	0.0474 (4)
H9A	0.1544	0.2149	0.2786	0.057*
C10	−0.0106 (3)	0.06409 (16)	0.31707 (6)	0.0410 (4)
C11	0.7076 (3)	0.25635 (16)	0.41359 (6)	0.0398 (4)
C12	0.8755 (3)	0.26618 (19)	0.45927 (7)	0.0505 (5)
H12A	0.8579	0.2089	0.4878	0.061*
C13	1.0691 (4)	0.36029 (19)	0.46282 (7)	0.0514 (5)
H13A	1.1819	0.3666	0.4937	0.062*
C14	1.0948 (3)	0.44545 (17)	0.42018 (7)	0.0446 (4)
C15	0.9273 (3)	0.43388 (19)	0.37409 (7)	0.0509 (5)
H15A	0.9456	0.4904	0.3453	0.061*
C16	0.7350 (3)	0.33980 (18)	0.37050 (7)	0.0477 (4)
H16A	0.6240	0.3321	0.3394	0.057*
C17	1.2921 (4)	0.5465 (2)	0.42332 (7)	0.0533 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0707 (9)	0.0608 (8)	0.0547 (8)	−0.0102 (7)	−0.0025 (7)	0.0170 (6)
N1	0.0445 (8)	0.0398 (8)	0.0427 (8)	0.0009 (6)	0.0035 (6)	−0.0017 (6)
N2	0.0509 (9)	0.0406 (8)	0.0417 (8)	−0.0023 (6)	0.0044 (7)	0.0056 (6)
N3	0.0691 (11)	0.0661 (12)	0.0849 (14)	−0.0198 (10)	0.0124 (10)	−0.0066 (10)
C1	0.0452 (10)	0.0373 (9)	0.0464 (9)	0.0016 (7)	0.0087 (8)	−0.0003 (7)
C2	0.0557 (11)	0.0443 (10)	0.0515 (11)	0.0010 (8)	0.0091 (9)	0.0054 (8)
C3	0.0612 (12)	0.0487 (11)	0.0638 (12)	−0.0088 (9)	0.0104 (10)	0.0127 (9)
C4	0.0503 (11)	0.0446 (10)	0.0680 (13)	−0.0085 (8)	0.0084 (10)	0.0016 (9)
C5	0.0459 (10)	0.0413 (10)	0.0505 (10)	−0.0009 (8)	0.0100 (8)	−0.0057 (8)
C6	0.0474 (10)	0.0532 (11)	0.0591 (12)	−0.0049 (9)	0.0031 (9)	−0.0092 (9)
C7	0.0531 (11)	0.0616 (12)	0.0501 (11)	0.0027 (10)	−0.0005 (9)	−0.0086 (9)
C8	0.0563 (11)	0.0534 (11)	0.0448 (10)	0.0023 (9)	0.0064 (9)	−0.0002 (8)
C9	0.0486 (10)	0.0461 (10)	0.0481 (10)	−0.0027 (8)	0.0084 (8)	−0.0017 (8)
C10	0.0426 (9)	0.0376 (9)	0.0436 (9)	0.0025 (7)	0.0087 (7)	−0.0034 (7)
C11	0.0425 (9)	0.0354 (9)	0.0421 (9)	0.0019 (7)	0.0080 (7)	−0.0002 (7)
C12	0.0621 (12)	0.0494 (11)	0.0392 (9)	−0.0036 (9)	0.0021 (9)	0.0042 (8)
C13	0.0551 (11)	0.0540 (11)	0.0436 (10)	−0.0057 (9)	−0.0016 (8)	−0.0025 (8)
C14	0.0435 (9)	0.0422 (9)	0.0488 (10)	0.0004 (8)	0.0090 (8)	−0.0023 (8)
C15	0.0520 (11)	0.0498 (10)	0.0517 (10)	−0.0005 (9)	0.0088 (9)	0.0122 (8)
C16	0.0483 (10)	0.0505 (10)	0.0429 (9)	−0.0007 (8)	−0.0007 (8)	0.0074 (8)
C17	0.0523 (11)	0.0541 (11)	0.0543 (11)	−0.0045 (9)	0.0098 (9)	−0.0034 (9)

O1—C2	1.254 (2)	C7—C8	1.387 (3)
N1—N2	1.3072 (19)	C7—H7A	0.9300
N1—C1	1.323 (2)	C8—C9	1.372 (2)
N2—C11	1.400 (2)	C8—H8A	0.9300
N2—H2A	0.8600	C9—C10	1.401 (2)
N3—C17	1.141 (2)	C9—H9A	0.9300
C1—C10	1.457 (2)	C11—C12	1.380 (2)
C1—C2	1.459 (2)	C11—C16	1.386 (2)
C2—C3	1.444 (3)	C12—C13	1.378 (2)
C3—C4	1.338 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.386 (2)
C4—C5	1.437 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.387 (2)
C5—C6	1.397 (2)	C14—C17	1.439 (3)
C5—C10	1.408 (2)	C15—C16	1.373 (2)
C6—C7	1.369 (3)	C15—H15A	0.9300
C6—H6A	0.9300	C16—H16A	0.9300
N2—N1—C1	120.28 (14)	C7—C8—H8A	119.6
N1—N2—C11	118.95 (14)	C8—C9—C10	120.83 (17)
N1—N2—H2A	120.5	C8—C9—H9A	119.6
C11—N2—H2A	120.5	C10—C9—H9A	119.6
N1—C1—C10	115.69 (15)	C9—C10—C5	118.39 (16)
N1—C1—C2	123.97 (16)	C9—C10—C1	122.33 (15)
C10—C1—C2	120.31 (15)	C5—C10—C1	119.27 (15)
O1—C2—C3	121.83 (17)	C12—C11—C16	120.16 (16)
O1—C2—C1	121.30 (16)	C12—C11—N2	118.66 (15)
C3—C2—C1	116.86 (17)	C16—C11—N2	121.18 (16)
C4—C3—C2	121.70 (18)	C13—C12—C11	120.41 (16)
C4—C3—H3A	119.1	C13—C12—H12A	119.8
C2—C3—H3A	119.1	C11—C12—H12A	119.8
C3—C4—C5	123.09 (17)	C12—C13—C14	119.67 (17)
C3—C4—H4A	118.5	C12—C13—H13A	120.2
C5—C4—H4A	118.5	C14—C13—H13A	120.2
C6—C5—C10	119.42 (16)	C13—C14—C15	119.65 (16)
C6—C5—C4	121.78 (16)	C13—C14—C17	120.72 (17)
C10—C5—C4	118.76 (16)	C15—C14—C17	119.63 (16)
C7—C6—C5	121.22 (17)	C16—C15—C14	120.67 (16)
C7—C6—H6A	119.4	C16—C15—H15A	119.7
C5—C6—H6A	119.4	C14—C15—H15A	119.7
C6—C7—C8	119.42 (18)	C15—C16—C11	119.44 (16)
C6—C7—H7A	120.3	C15—C16—H16A	120.3
C8—C7—H7A	120.3	C11—C16—H16A	120.3
C9—C8—C7	120.72 (18)	N3—C17—C14	179.1 (2)
C9—C8—H8A	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.91	2.580 (2)	133
C12—H12A···O1i	0.93	2.45	3.362 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.91	2.580 (2)	133
C12—H12A⋯O1i	0.93	2.45	3.362 (2)	166

Symmetry code: (i) .