organic compounds
(E)-1-(4-Fluorophenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium
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
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 (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.
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 .
details are summarized in Table 2Structural data
CCDC reference: 1526368
https://doi.org/10.1107/S2414314617000396/hb4108sup1.cif
contains datablock I. DOI: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
Data collection: APEX2 (Bruker, 2006); cell
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).C16H11FN2O | F(000) = 552 |
Mr = 266.27 | Dx = 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 |
Bruker APEXII diffractometer | 1886 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | h = −15→17 |
Tmin = 0.990, Tmax = 0.990 | k = −17→13 |
10648 measured reflections | l = −8→7 |
2815 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)] = 0.042 | 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(Fo2) + (0.0721P)2 + 0.0881P] where P = (Fo2 + 2Fc2)/3 |
2817 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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 |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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.
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