(E)-1-(4-Fluoro­phen­yl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

Bougueria, H.; Chetioui, S.; Mili, A.; Bouaoud, S. eddine; Merazig, H.

doi:10.1107/S2414314617000396

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170039

https://doi.org/10.1107/S2414314617000396

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(E)-1-(4-Fluorophenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

Hassiba Bougueria,^a,^b ^* Souheyla Chetioui,^a Assia Mili,^a Salah eddine Bouaoud ^a and Hocine Merazig ^a

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Département de Chimie, Université Mentouri de Constantine, 25000 Constantine, Algeria, and ^bCentre Universitaire Abd El Hafid Boussouf, Mila, 43000 Mila, Algeria
^*Correspondence e-mail: naadia.saadouni@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 December 2016; accepted 9 January 2017; online 13 January 2017)

In the title zwitterion, C₁₆H₁₁FN₂O, which belongs to the family of azo dyes, the dihedral angle between the benzene ring and the naphthalene ring system is 15.33 (7)° and an intramolecular N—H⋯O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by weak C—H⋯O hydrogen bonds generate R₂²(16) loops. Aromatic π–π stacking [centroid–centroid distance = 3.585 (11) Å] is also observed.

Keywords: crystal structure; hydrogen bonding; π–π stacking; zwitterion.

CCDC reference: 1526368

Structure description

The structures and properties of azo dyes (solubility, habit, stability, colour) are dependent on their solid-state structures (Kennedy et al., 2004 ). As part of our studies in this area, we now describe the structure of the title compound, which shows zwitterionic behaviour (i.e. proton transfer from the naphthol group to the azo group) in the solid state.

The dihedral angle between the benzene ring and the naphthalene ring system is 15.33 (7)° and an intramolecular N—H⋯O hydrogen bond (Fig. 1 and Table 1) closes an S(6) ring. In the crystal, inversion dimers linked by weak C—H⋯O hydrogen bonds generate $[R_{2}^{2}]$ (16) loops. The dimers are linked through π–π stacking between the benzene ring and naphthalene ring systems of adjacent molecules, the centroid–centroid distance between the C1-ring and C9-ring being 3.585 (11) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.86	1.83	2.5342 (18)	138
C3—H3⋯O1ⁱ	0.93	2.54	3.417 (2)	157
Symmetry code: (i) -x+1, -y+1, -z.

Figure 1
The molecular structure with displacement ellipsoids drawn at the 50% probability level.

Synthesis and crystallization

The title compound was obtained through the diazotization of 4-fluoroaniline followed by a coupling reaction with 2-naphthol according to the established procedure (Wang et al., 2003 ). Colourless prisms of were obtained by slow evaporation of THF–H₂O (1:1 v/v) solution at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₁FN₂O
M_r	266.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.211 (3), 13.685 (2), 6.8580 (14)
β (°)	92.971 (11)
V (Å³)	1238.2 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.1 × 0.1 × 0.1

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2006 )
T_min, T_max	0.990, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	10648, 2815, 1886
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.124, 0.97
No. of reflections	2817
No. of parameters	182
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2006), SHELXS86 and SHELXL97 (Sheldrick, 2008 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1526368

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617000396/hb4108sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617000396/hb4108Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617000396/hb4108Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

(E)-1-(4-Fluorophenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium top

Crystal data top

C₁₆H₁₁FN₂O	F(000) = 552
M_r = 266.27	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2528 reflections
a = 13.211 (3) Å	θ = 3.0–27.1°
b = 13.685 (2) Å	µ = 0.10 mm⁻¹
c = 6.8580 (14) Å	T = 293 K
β = 92.971 (11)°	Prism, colourless
V = 1238.2 (4) Å³	0.1 × 0.1 × 0.1 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	1886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −15→17
T_min = 0.990, T_max = 0.990	k = −17→13
10648 measured reflections	l = −8→7
2815 independent reflections

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0721P)² + 0.0881P] where P = (F_o² + 2F_c²)/3
2817 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.06264 (7)	0.21274 (7)	0.05713 (17)	0.0439 (4)
O1	0.48253 (8)	0.60742 (7)	0.13349 (17)	0.0293 (4)
N1	0.30356 (10)	0.54101 (8)	0.09440 (18)	0.0228 (4)
N2	0.26550 (10)	0.62815 (8)	0.09470 (18)	0.0218 (4)
C1	0.12128 (12)	0.29487 (11)	0.0642 (3)	0.0280 (5)
C2	0.22314 (12)	0.28554 (11)	0.0370 (3)	0.0290 (5)
C3	0.28263 (12)	0.36936 (11)	0.0479 (2)	0.0259 (5)
C4	0.23846 (11)	0.45913 (10)	0.0844 (2)	0.0216 (4)
C5	0.13491 (12)	0.46609 (11)	0.1111 (2)	0.0261 (5)
C6	0.07590 (13)	0.38305 (11)	0.1005 (3)	0.0290 (5)
C9	0.44015 (12)	0.69218 (11)	0.1297 (2)	0.0232 (5)
C10	0.50143 (12)	0.77902 (11)	0.1477 (2)	0.0276 (5)
C11	0.45942 (12)	0.86927 (11)	0.1419 (2)	0.0259 (5)
C12	0.35172 (12)	0.88390 (10)	0.1183 (2)	0.0227 (5)
C13	0.30979 (13)	0.97866 (11)	0.1140 (2)	0.0267 (5)
C14	0.20713 (13)	0.99159 (11)	0.0913 (2)	0.0300 (5)
C15	0.14335 (12)	0.91015 (11)	0.0711 (2)	0.0286 (5)
C16	0.18212 (12)	0.81701 (11)	0.0766 (2)	0.0258 (5)
C17	0.28710 (12)	0.80125 (10)	0.1012 (2)	0.0209 (5)
C18	0.33171 (11)	0.70416 (10)	0.1080 (2)	0.0205 (4)
H1N	0.36822	0.53301	0.10028	0.0274*
H2	0.25148	0.22489	0.01198	0.0348*
H3	0.35187	0.36530	0.03071	0.0311*
H5	0.10579	0.52639	0.13602	0.0313*
H6	0.00662	0.38655	0.11756	0.0347*
H10	0.57148	0.77297	0.16368	0.0331*
H11	0.50162	0.92359	0.15343	0.0311*
H13	0.35220	1.03278	0.12652	0.0320*
H14	0.17985	1.05425	0.08938	0.0360*
H15	0.07371	0.91924	0.05368	0.0343*
H16	0.13844	0.76383	0.06400	0.0309*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0319 (6)	0.0280 (5)	0.0717 (8)	−0.0104 (4)	0.0010 (5)	−0.0031 (5)
O1	0.0253 (6)	0.0244 (6)	0.0381 (7)	0.0032 (5)	0.0011 (5)	0.0011 (5)
N1	0.0210 (7)	0.0209 (7)	0.0265 (7)	0.0009 (5)	0.0008 (5)	0.0009 (5)
N2	0.0278 (8)	0.0183 (7)	0.0194 (7)	0.0002 (5)	0.0015 (5)	−0.0003 (5)
C1	0.0265 (9)	0.0210 (8)	0.0360 (9)	−0.0070 (7)	−0.0019 (7)	0.0014 (7)
C2	0.0284 (9)	0.0189 (8)	0.0398 (10)	0.0022 (7)	0.0018 (8)	−0.0008 (7)
C3	0.0237 (9)	0.0239 (8)	0.0301 (9)	0.0009 (6)	0.0021 (7)	0.0020 (6)
C4	0.0245 (8)	0.0206 (7)	0.0194 (8)	−0.0029 (6)	−0.0008 (6)	0.0021 (6)
C5	0.0267 (9)	0.0216 (8)	0.0299 (9)	0.0036 (7)	0.0009 (7)	−0.0009 (6)
C6	0.0214 (8)	0.0295 (9)	0.0360 (10)	0.0000 (7)	0.0012 (7)	−0.0002 (7)
C9	0.0247 (9)	0.0253 (8)	0.0197 (8)	0.0003 (7)	0.0023 (6)	0.0006 (6)
C10	0.0225 (8)	0.0312 (9)	0.0289 (9)	−0.0045 (7)	0.0005 (7)	−0.0041 (7)
C11	0.0285 (9)	0.0245 (8)	0.0248 (8)	−0.0082 (7)	0.0018 (7)	−0.0041 (6)
C12	0.0281 (9)	0.0235 (8)	0.0166 (8)	−0.0031 (7)	0.0029 (7)	−0.0006 (6)
C13	0.0335 (10)	0.0211 (8)	0.0256 (8)	−0.0058 (7)	0.0031 (7)	−0.0016 (6)
C14	0.0411 (10)	0.0206 (8)	0.0285 (9)	0.0042 (7)	0.0036 (7)	0.0011 (6)
C15	0.0253 (9)	0.0254 (8)	0.0352 (9)	0.0032 (7)	0.0018 (7)	0.0013 (7)
C16	0.0262 (9)	0.0211 (8)	0.0300 (9)	−0.0035 (7)	0.0018 (7)	−0.0002 (6)
C17	0.0248 (9)	0.0210 (8)	0.0170 (7)	−0.0009 (6)	0.0027 (6)	0.0001 (6)
C18	0.0244 (8)	0.0203 (7)	0.0170 (7)	−0.0019 (6)	0.0026 (6)	0.0001 (6)

Geometric parameters (Å, º) top

F1—C1	1.3645 (18)	C12—C13	1.410 (2)
O1—C9	1.2877 (18)	C13—C14	1.369 (2)
N1—N2	1.2942 (16)	C14—C15	1.400 (2)
N1—C4	1.4120 (19)	C15—C16	1.374 (2)
N2—C18	1.3591 (19)	C16—C17	1.405 (2)
N1—H1N	0.8600	C17—C18	1.453 (2)
C1—C2	1.374 (2)	C2—H2	0.9300
C1—C6	1.376 (2)	C3—H3	0.9300
C2—C3	1.390 (2)	C5—H5	0.9300
C3—C4	1.388 (2)	C6—H6	0.9300
C4—C5	1.393 (2)	C10—H10	0.9300
C5—C6	1.378 (2)	C11—H11	0.9300
C9—C10	1.440 (2)	C13—H13	0.9300
C9—C18	1.442 (2)	C14—H14	0.9300
C10—C11	1.354 (2)	C15—H15	0.9300
C11—C12	1.438 (2)	C16—H16	0.9300
C12—C17	1.418 (2)

N2—N1—C4	119.71 (13)	C12—C17—C18	119.02 (14)
N1—N2—C18	117.17 (13)	C16—C17—C18	122.71 (13)
C4—N1—H1N	120.00	C12—C17—C16	118.27 (13)
N2—N1—H1N	120.00	C9—C18—C17	120.42 (13)
F1—C1—C6	118.49 (14)	N2—C18—C9	123.53 (13)
C2—C1—C6	123.03 (15)	N2—C18—C17	116.05 (13)
F1—C1—C2	118.48 (13)	C1—C2—H2	121.00
C1—C2—C3	118.09 (14)	C3—C2—H2	121.00
C2—C3—C4	119.87 (14)	C2—C3—H3	120.00
N1—C4—C3	116.76 (13)	C4—C3—H3	120.00
C3—C4—C5	120.60 (13)	C4—C5—H5	120.00
N1—C4—C5	122.63 (13)	C6—C5—H5	120.00
C4—C5—C6	119.57 (14)	C1—C6—H6	121.00
C1—C6—C5	118.83 (15)	C5—C6—H6	121.00
C10—C9—C18	117.79 (13)	C9—C10—H10	119.00
O1—C9—C10	119.99 (14)	C11—C10—H10	119.00
O1—C9—C18	122.22 (13)	C10—C11—H11	119.00
C9—C10—C11	121.52 (15)	C12—C11—H11	119.00
C10—C11—C12	122.15 (14)	C12—C13—H13	120.00
C11—C12—C17	119.09 (13)	C14—C13—H13	120.00
C13—C12—C17	119.85 (14)	C13—C14—H14	120.00
C11—C12—C13	121.06 (14)	C15—C14—H14	120.00
C12—C13—C14	120.48 (14)	C14—C15—H15	120.00
C13—C14—C15	119.75 (14)	C16—C15—H15	120.00
C14—C15—C16	120.96 (15)	C15—C16—H16	120.00
C15—C16—C17	120.67 (14)	C17—C16—H16	120.00

C4—N1—N2—C18	178.88 (12)	C10—C9—C18—C17	1.1 (2)
N2—N1—C4—C3	168.30 (13)	C9—C10—C11—C12	0.2 (2)
N2—N1—C4—C5	−12.3 (2)	C10—C11—C12—C13	179.58 (13)
N1—N2—C18—C9	−2.7 (2)	C10—C11—C12—C17	0.2 (2)
N1—N2—C18—C17	177.94 (12)	C11—C12—C13—C14	179.94 (15)
F1—C1—C2—C3	−178.87 (16)	C17—C12—C13—C14	−0.7 (2)
C6—C1—C2—C3	0.3 (3)	C11—C12—C17—C16	−179.48 (13)
F1—C1—C6—C5	178.93 (16)	C11—C12—C17—C18	−0.02 (19)
C2—C1—C6—C5	−0.3 (3)	C13—C12—C17—C16	1.2 (2)
C1—C2—C3—C4	−0.3 (3)	C13—C12—C17—C18	−179.37 (13)
C2—C3—C4—N1	179.71 (14)	C12—C13—C14—C15	−0.4 (2)
C2—C3—C4—C5	0.3 (2)	C13—C14—C15—C16	1.0 (2)
N1—C4—C5—C6	−179.62 (15)	C14—C15—C16—C17	−0.5 (2)
C3—C4—C5—C6	−0.2 (2)	C15—C16—C17—C12	−0.6 (2)
C4—C5—C6—C1	0.2 (3)	C15—C16—C17—C18	179.97 (14)
O1—C9—C10—C11	179.18 (13)	C12—C17—C18—N2	178.74 (13)
C18—C9—C10—C11	−0.9 (2)	C12—C17—C18—C9	−0.7 (2)
O1—C9—C18—N2	1.7 (2)	C16—C17—C18—N2	−1.8 (2)
O1—C9—C18—C17	−178.98 (13)	C16—C17—C18—C9	178.78 (13)
C10—C9—C18—N2	−178.25 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.86	1.83	2.5342 (18)	138
C3—H3···O1ⁱ	0.93	2.54	3.417 (2)	157

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

We thank all researchers of the CHEMS Research Unit of the University of Constantine Algeria for the valuable assistance they have provided us throughout the realization of this work.

References

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