organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

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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 ππ stacking [centroid–centroid distance = 3.585 (11) Å] is also observed.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The structures and properties of azo dyes (solubility, habit, stability, colour) are dependent on their solid-state structures (Kennedy et al., 2004[Kennedy, A. R., Kirkhouse, J. B. A., McCarney, K. M., Puissegur, O., Smith, W. E., Staunton, E., Teat, S. J., Cherryman, J. C. & James, R. (2004). Chem. Eur. J. 10, 4606-4615.]). 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[link] and Table 1[link]) 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 ππ 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 DA 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]
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[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigments, 57, 77-86.]). 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[link].

Table 2
Experimental details

Crystal data
Chemical formula C16H11FN2O
Mr 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)
V3) 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[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.990, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections 10648, 2815, 1886
Rint 0.033
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.26, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS86 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data


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
C16H11FN2OF(000) = 552
Mr = 266.27Dx = 1.428 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2528 reflections
a = 13.211 (3) Åθ = 3.0–27.1°
b = 13.685 (2) ŵ = 0.10 mm1
c = 6.8580 (14) ÅT = 293 K
β = 92.971 (11)°Prism, colourless
V = 1238.2 (4) Å30.1 × 0.1 × 0.1 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
1886 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1517
Tmin = 0.990, Tmax = 0.990k = 1713
10648 measured reflectionsl = 87
2815 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.0721P)2 + 0.0881P]
where P = (Fo2 + 2Fc2)/3
2817 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
F10.06264 (7)0.21274 (7)0.05713 (17)0.0439 (4)
O10.48253 (8)0.60742 (7)0.13349 (17)0.0293 (4)
N10.30356 (10)0.54101 (8)0.09440 (18)0.0228 (4)
N20.26550 (10)0.62815 (8)0.09470 (18)0.0218 (4)
C10.12128 (12)0.29487 (11)0.0642 (3)0.0280 (5)
C20.22314 (12)0.28554 (11)0.0370 (3)0.0290 (5)
C30.28263 (12)0.36936 (11)0.0479 (2)0.0259 (5)
C40.23846 (11)0.45913 (10)0.0844 (2)0.0216 (4)
C50.13491 (12)0.46609 (11)0.1111 (2)0.0261 (5)
C60.07590 (13)0.38305 (11)0.1005 (3)0.0290 (5)
C90.44015 (12)0.69218 (11)0.1297 (2)0.0232 (5)
C100.50143 (12)0.77902 (11)0.1477 (2)0.0276 (5)
C110.45942 (12)0.86927 (11)0.1419 (2)0.0259 (5)
C120.35172 (12)0.88390 (10)0.1183 (2)0.0227 (5)
C130.30979 (13)0.97866 (11)0.1140 (2)0.0267 (5)
C140.20713 (13)0.99159 (11)0.0913 (2)0.0300 (5)
C150.14335 (12)0.91015 (11)0.0711 (2)0.0286 (5)
C160.18212 (12)0.81701 (11)0.0766 (2)0.0258 (5)
C170.28710 (12)0.80125 (10)0.1012 (2)0.0209 (5)
C180.33171 (11)0.70416 (10)0.1080 (2)0.0205 (4)
H1N0.368220.533010.100280.0274*
H20.251480.224890.011980.0348*
H30.351870.365300.030710.0311*
H50.105790.526390.136020.0313*
H60.006620.386550.117560.0347*
H100.571480.772970.163680.0331*
H110.501620.923590.153430.0311*
H130.352201.032780.126520.0320*
H140.179851.054250.089380.0360*
H150.073710.919240.053680.0343*
H160.138440.763830.064000.0309*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0319 (6)0.0280 (5)0.0717 (8)0.0104 (4)0.0010 (5)0.0031 (5)
O10.0253 (6)0.0244 (6)0.0381 (7)0.0032 (5)0.0011 (5)0.0011 (5)
N10.0210 (7)0.0209 (7)0.0265 (7)0.0009 (5)0.0008 (5)0.0009 (5)
N20.0278 (8)0.0183 (7)0.0194 (7)0.0002 (5)0.0015 (5)0.0003 (5)
C10.0265 (9)0.0210 (8)0.0360 (9)0.0070 (7)0.0019 (7)0.0014 (7)
C20.0284 (9)0.0189 (8)0.0398 (10)0.0022 (7)0.0018 (8)0.0008 (7)
C30.0237 (9)0.0239 (8)0.0301 (9)0.0009 (6)0.0021 (7)0.0020 (6)
C40.0245 (8)0.0206 (7)0.0194 (8)0.0029 (6)0.0008 (6)0.0021 (6)
C50.0267 (9)0.0216 (8)0.0299 (9)0.0036 (7)0.0009 (7)0.0009 (6)
C60.0214 (8)0.0295 (9)0.0360 (10)0.0000 (7)0.0012 (7)0.0002 (7)
C90.0247 (9)0.0253 (8)0.0197 (8)0.0003 (7)0.0023 (6)0.0006 (6)
C100.0225 (8)0.0312 (9)0.0289 (9)0.0045 (7)0.0005 (7)0.0041 (7)
C110.0285 (9)0.0245 (8)0.0248 (8)0.0082 (7)0.0018 (7)0.0041 (6)
C120.0281 (9)0.0235 (8)0.0166 (8)0.0031 (7)0.0029 (7)0.0006 (6)
C130.0335 (10)0.0211 (8)0.0256 (8)0.0058 (7)0.0031 (7)0.0016 (6)
C140.0411 (10)0.0206 (8)0.0285 (9)0.0042 (7)0.0036 (7)0.0011 (6)
C150.0253 (9)0.0254 (8)0.0352 (9)0.0032 (7)0.0018 (7)0.0013 (7)
C160.0262 (9)0.0211 (8)0.0300 (9)0.0035 (7)0.0018 (7)0.0002 (6)
C170.0248 (9)0.0210 (8)0.0170 (7)0.0009 (6)0.0027 (6)0.0001 (6)
C180.0244 (8)0.0203 (7)0.0170 (7)0.0019 (6)0.0026 (6)0.0001 (6)
Geometric parameters (Å, º) top
F1—C11.3645 (18)C12—C131.410 (2)
O1—C91.2877 (18)C13—C141.369 (2)
N1—N21.2942 (16)C14—C151.400 (2)
N1—C41.4120 (19)C15—C161.374 (2)
N2—C181.3591 (19)C16—C171.405 (2)
N1—H1N0.8600C17—C181.453 (2)
C1—C21.374 (2)C2—H20.9300
C1—C61.376 (2)C3—H30.9300
C2—C31.390 (2)C5—H50.9300
C3—C41.388 (2)C6—H60.9300
C4—C51.393 (2)C10—H100.9300
C5—C61.378 (2)C11—H110.9300
C9—C101.440 (2)C13—H130.9300
C9—C181.442 (2)C14—H140.9300
C10—C111.354 (2)C15—H150.9300
C11—C121.438 (2)C16—H160.9300
C12—C171.418 (2)
N2—N1—C4119.71 (13)C12—C17—C18119.02 (14)
N1—N2—C18117.17 (13)C16—C17—C18122.71 (13)
C4—N1—H1N120.00C12—C17—C16118.27 (13)
N2—N1—H1N120.00C9—C18—C17120.42 (13)
F1—C1—C6118.49 (14)N2—C18—C9123.53 (13)
C2—C1—C6123.03 (15)N2—C18—C17116.05 (13)
F1—C1—C2118.48 (13)C1—C2—H2121.00
C1—C2—C3118.09 (14)C3—C2—H2121.00
C2—C3—C4119.87 (14)C2—C3—H3120.00
N1—C4—C3116.76 (13)C4—C3—H3120.00
C3—C4—C5120.60 (13)C4—C5—H5120.00
N1—C4—C5122.63 (13)C6—C5—H5120.00
C4—C5—C6119.57 (14)C1—C6—H6121.00
C1—C6—C5118.83 (15)C5—C6—H6121.00
C10—C9—C18117.79 (13)C9—C10—H10119.00
O1—C9—C10119.99 (14)C11—C10—H10119.00
O1—C9—C18122.22 (13)C10—C11—H11119.00
C9—C10—C11121.52 (15)C12—C11—H11119.00
C10—C11—C12122.15 (14)C12—C13—H13120.00
C11—C12—C17119.09 (13)C14—C13—H13120.00
C13—C12—C17119.85 (14)C13—C14—H14120.00
C11—C12—C13121.06 (14)C15—C14—H14120.00
C12—C13—C14120.48 (14)C14—C15—H15120.00
C13—C14—C15119.75 (14)C16—C15—H15120.00
C14—C15—C16120.96 (15)C15—C16—H16120.00
C15—C16—C17120.67 (14)C17—C16—H16120.00
C4—N1—N2—C18178.88 (12)C10—C9—C18—C171.1 (2)
N2—N1—C4—C3168.30 (13)C9—C10—C11—C120.2 (2)
N2—N1—C4—C512.3 (2)C10—C11—C12—C13179.58 (13)
N1—N2—C18—C92.7 (2)C10—C11—C12—C170.2 (2)
N1—N2—C18—C17177.94 (12)C11—C12—C13—C14179.94 (15)
F1—C1—C2—C3178.87 (16)C17—C12—C13—C140.7 (2)
C6—C1—C2—C30.3 (3)C11—C12—C17—C16179.48 (13)
F1—C1—C6—C5178.93 (16)C11—C12—C17—C180.02 (19)
C2—C1—C6—C50.3 (3)C13—C12—C17—C161.2 (2)
C1—C2—C3—C40.3 (3)C13—C12—C17—C18179.37 (13)
C2—C3—C4—N1179.71 (14)C12—C13—C14—C150.4 (2)
C2—C3—C4—C50.3 (2)C13—C14—C15—C161.0 (2)
N1—C4—C5—C6179.62 (15)C14—C15—C16—C170.5 (2)
C3—C4—C5—C60.2 (2)C15—C16—C17—C120.6 (2)
C4—C5—C6—C10.2 (3)C15—C16—C17—C18179.97 (14)
O1—C9—C10—C11179.18 (13)C12—C17—C18—N2178.74 (13)
C18—C9—C10—C110.9 (2)C12—C17—C18—C90.7 (2)
O1—C9—C18—N21.7 (2)C16—C17—C18—N21.8 (2)
O1—C9—C18—C17178.98 (13)C16—C17—C18—C9178.78 (13)
C10—C9—C18—N2178.25 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.861.832.5342 (18)138
C3—H3···O1i0.932.543.417 (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

First citationBruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationKennedy, A. R., Kirkhouse, J. B. A., McCarney, K. M., Puissegur, O., Smith, W. E., Staunton, E., Teat, S. J., Cherryman, J. C. & James, R. (2004). Chem. Eur. J. 10, 4606–4615.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigments, 57, 77–86.  Web of Science CrossRef CAS Google Scholar

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