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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o218.
Published online 2007 December 6. doi:  10.1107/S1600536807064549
PMCID: PMC2915279

1-(4-Methyl­phenyl­diazo­nium­yl)-2-naphtholate

Abstract

In the title compound, C17H14N2O, the dihedral angle between the benzene ring and naphthalene ring system is 11.0 (3)°. The azo group adopts an anti configuration and an intra­molecular N—H(...)O hydrogen bond exists. Mol­ecules are packed by π–π inter­actions between adjacent mol­ecule (closest approach between centroids of benzene and naphthalene rings of 3.501 Å).

Related literature

For related literature, see: Lee et al. (2004 [triangle]); Oueslati et al. (2004 [triangle]); Wang et al. (2003 [triangle]).

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Object name is e-64-0o218-scheme1.jpg

Experimental

Crystal data

  • C17H14N2O
  • M r = 262.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o218-efi1.jpg
  • a = 13.6740 (4) Å
  • b = 13.8000 (4) Å
  • c = 7.1430 (2) Å
  • β = 95.752 (2)°
  • V = 1341.11 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.984, T max = 0.992
  • 14681 measured reflections
  • 2913 independent reflections
  • 1802 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.149
  • S = 1.04
  • 2913 reflections
  • 185 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2001 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064549/hj2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064549/hj2006Isup2.hkl

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

Acknowledgments

We gratefully acknowledge the financial support of the National Science Funds for Distinguished Young Scholars of Hubei Province, People’s Republic of China (Grant No. 2006ABB038), the Outstanding Mid-Young Scholars’ Programs, Hubei Provincial Department of Education (Q20072203) and the Project sponsored by SRF for ROCS, SEM (200724).

supplementary crystallographic information

Comment

Azo compounds are very important in the fields of dyes, pigments and advanced materials (Lee et al., 2004; Oueslati et al., 2004). Azo dyes are synthetic colours that contain an azo group, as part of the structure. Azo groups do not occur naturally. Many azo compounds have been synthesized by the diazotization and diazo coupling reaction (Wang et al., 2003). The title compound (I) was obtained through the diazotization of 4-methylaniline followed by a coupling reaction with 2-naphthol.

The molecular structure of the title compound is illustrated in figure 1, where the molecule adopts an anti configuration with the two aryl groups residing on the opposite sides of azo group. The dihedral angle between the benzene ring and naphthalene ring is 11.0 (3)°. An intramolecular N—H···O hydrogen bond exists in each molecule (Table 1). Interestingly, the hydrogen atom in the OH group has transfer to the N atom in the azo group to form a dipolar ion; the difference Fourier map indicated that the hydrogen site location is closer to nitrogen atom of the azo group. The molecules are packed by the π···π interactions with the closest approach between centroids of aromatic rings of 3.501Å (symmetry equivalent x, -y + 1, z - 1/2).

Experimental

The title compound was prepared by a similar method of other aromatic azo compounds(Wang et al., 2003). Single crystals of (I) were obtained by slow evaporation from a petroleum ether-ethyl acetate (2:1 v/v) solution system.

Refinement

H atoms were positioned geometrically at distances of 0.93 (CH), and 0.96Å (CH3) from the parent C atoms, a riding model was used during the refinement process. The Uiso values were constrained to be 1.2Ueq of the carrier atom, except for methyl H atoms that were constrained to 1.5Ueq of the C atom.

Figures

Fig. 1.
The structure of (I) showing the atom-numbering with Displacement ellipsoids are drawn at the 30% probability level. The intramolecular H bonded is shown with a dashed line.

Crystal data

C17H14N2OF000 = 552
Mr = 262.30Dx = 1.299 Mg m3
Monoclinic, P2(1)/cMelting point: 407 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 13.6740 (4) ÅCell parameters from 2246 reflections
b = 13.8000 (4) Åθ = 3.0–23.4º
c = 7.1430 (2) ŵ = 0.08 mm1
β = 95.752 (2)ºT = 293 (2) K
V = 1341.11 (7) Å3Needle, red
Z = 40.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART Apex CCD area detector diffractometer2913 independent reflections
Radiation source: fine-focus sealed tube1802 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 293(2) Kθmax = 27.0º
phi and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.984, Tmax = 0.992k = −17→16
14681 measured reflectionsl = −9→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149  w = 1/[σ2(Fo2) + (0.0816P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2913 reflectionsΔρmax = 0.18 e Å3
185 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

xyzUiso*/Ueq
C10.75809 (11)−0.03170 (11)0.1047 (2)0.0516 (4)
C20.72115 (12)−0.12434 (12)0.0942 (3)0.0649 (5)
H20.6535−0.13420.08350.078*
C30.78410 (13)−0.20284 (12)0.0996 (3)0.0687 (5)
H30.7580−0.26510.09420.082*
C40.88439 (12)−0.19111 (12)0.1126 (2)0.0574 (4)
C50.91975 (12)−0.09723 (12)0.1207 (2)0.0641 (5)
H50.9873−0.08720.12860.077*
C60.85837 (11)−0.01801 (12)0.1176 (2)0.0611 (5)
H60.88440.04430.12410.073*
C70.65467 (11)0.20510 (11)0.1130 (2)0.0508 (4)
C80.55267 (12)0.18838 (12)0.1327 (2)0.0581 (4)
C90.49147 (13)0.27144 (14)0.1539 (2)0.0689 (5)
H90.42530.26250.16900.083*
C100.52800 (13)0.36158 (13)0.1524 (2)0.0689 (5)
H100.48600.41350.16670.083*
C110.62899 (12)0.38124 (11)0.1296 (2)0.0580 (4)
C120.66538 (15)0.47637 (13)0.1275 (3)0.0735 (5)
H120.62340.52820.14190.088*
C130.76133 (15)0.49346 (13)0.1045 (3)0.0803 (6)
H130.78480.55670.10420.096*
C140.82436 (14)0.41645 (13)0.0816 (3)0.0744 (5)
H140.88980.42840.06420.089*
C150.79103 (12)0.32326 (12)0.0843 (2)0.0638 (5)
H150.83430.27250.06960.077*
C160.69297 (11)0.30295 (11)0.1089 (2)0.0522 (4)
C170.95297 (13)−0.27743 (13)0.1212 (3)0.0742 (5)
H17A0.9433−0.31590.22980.111*
H17B1.0198−0.25520.12950.111*
H17C0.9393−0.31590.00970.111*
N10.69010 (9)0.04469 (9)0.10377 (18)0.0561 (4)
H1A0.6116 (12)0.0421 (10)0.109 (2)0.067*
N20.72155 (9)0.13342 (9)0.10388 (17)0.0531 (4)
O10.51595 (8)0.10306 (8)0.13228 (18)0.0726 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0530 (9)0.0517 (9)0.0499 (9)0.0026 (7)0.0044 (7)0.0032 (7)
C20.0512 (9)0.0586 (11)0.0846 (13)−0.0007 (8)0.0055 (8)0.0000 (9)
C30.0636 (11)0.0507 (10)0.0915 (14)−0.0012 (8)0.0071 (9)−0.0010 (9)
C40.0636 (11)0.0586 (11)0.0506 (10)0.0090 (8)0.0090 (7)0.0010 (7)
C50.0497 (9)0.0699 (12)0.0732 (12)0.0028 (8)0.0089 (8)0.0042 (9)
C60.0538 (9)0.0549 (10)0.0749 (12)−0.0034 (8)0.0084 (8)0.0030 (8)
C70.0528 (9)0.0539 (10)0.0449 (9)0.0069 (7)0.0005 (7)0.0001 (7)
C80.0580 (10)0.0647 (11)0.0511 (10)0.0056 (8)0.0030 (7)0.0014 (8)
C90.0545 (10)0.0796 (13)0.0727 (12)0.0137 (9)0.0069 (8)−0.0056 (9)
C100.0704 (12)0.0710 (12)0.0646 (12)0.0213 (9)0.0029 (9)−0.0069 (9)
C110.0690 (11)0.0560 (10)0.0471 (9)0.0095 (8)−0.0028 (7)−0.0016 (7)
C120.0913 (14)0.0554 (11)0.0708 (12)0.0138 (10)−0.0060 (10)−0.0029 (9)
C130.0980 (15)0.0557 (12)0.0844 (14)−0.0077 (10)−0.0045 (11)0.0005 (9)
C140.0726 (12)0.0633 (12)0.0858 (13)−0.0067 (9)0.0014 (9)0.0053 (10)
C150.0634 (11)0.0575 (11)0.0697 (12)0.0017 (8)0.0022 (8)0.0010 (8)
C160.0571 (10)0.0551 (10)0.0430 (8)0.0065 (7)−0.0020 (7)0.0000 (7)
C170.0766 (12)0.0733 (12)0.0735 (12)0.0201 (9)0.0111 (9)−0.0002 (9)
N10.0504 (8)0.0528 (9)0.0650 (9)0.0024 (6)0.0056 (6)0.0043 (6)
N20.0571 (8)0.0510 (8)0.0507 (8)0.0023 (6)0.0034 (6)0.0015 (6)
O10.0574 (7)0.0664 (8)0.0945 (10)−0.0048 (6)0.0099 (6)0.0028 (6)

Geometric parameters (Å, °)

C1—C21.374 (2)C9—H90.9300
C1—C61.378 (2)C10—C111.432 (2)
C1—N11.4051 (19)C10—H100.9300
C2—C31.382 (2)C11—C121.405 (2)
C2—H20.9300C11—C161.407 (2)
C3—C41.375 (2)C12—C131.359 (3)
C3—H30.9300C12—H120.9300
C4—C51.382 (2)C13—C141.388 (3)
C4—C171.513 (2)C13—H130.9300
C5—C61.377 (2)C14—C151.365 (2)
C5—H50.9300C14—H140.9300
C6—H60.9300C15—C161.398 (2)
C7—N21.3531 (18)C15—H150.9300
C7—C81.435 (2)C17—H17A0.9600
C7—C161.450 (2)C17—H17B0.9600
C8—O11.2799 (18)C17—H17C0.9600
C8—C91.436 (2)N1—N21.2978 (16)
C9—C101.341 (2)N1—H1A1.078 (16)
C2—C1—C6119.29 (14)C11—C10—H10118.6
C2—C1—N1117.28 (14)C12—C11—C16119.45 (16)
C6—C1—N1123.43 (14)C12—C11—C10121.66 (15)
C1—C2—C3120.22 (15)C16—C11—C10118.89 (15)
C1—C2—H2119.9C13—C12—C11120.72 (17)
C3—C2—H2119.9C13—C12—H12119.6
C4—C3—C2121.60 (15)C11—C12—H12119.6
C4—C3—H3119.2C12—C13—C14119.98 (17)
C2—C3—H3119.2C12—C13—H13120.0
C3—C4—C5117.10 (14)C14—C13—H13120.0
C3—C4—C17121.33 (15)C15—C14—C13120.49 (18)
C5—C4—C17121.56 (15)C15—C14—H14119.8
C6—C5—C4122.24 (15)C13—C14—H14119.8
C6—C5—H5118.9C14—C15—C16121.10 (16)
C4—C5—H5118.9C14—C15—H15119.5
C5—C6—C1119.54 (15)C16—C15—H15119.5
C5—C6—H6120.2C15—C16—C11118.26 (15)
C1—C6—H6120.2C15—C16—C7122.84 (14)
N2—C7—C8123.75 (14)C11—C16—C7118.90 (14)
N2—C7—C16115.64 (13)C4—C17—H17A109.5
C8—C7—C16120.57 (14)C4—C17—H17B109.5
O1—C8—C7122.20 (14)H17A—C17—H17B109.5
O1—C8—C9120.12 (15)C4—C17—H17C109.5
C7—C8—C9117.68 (15)H17A—C17—H17C109.5
C10—C9—C8121.20 (16)H17B—C17—H17C109.5
C10—C9—H9119.4N2—N1—C1119.26 (13)
C8—C9—H9119.4N2—N1—H1A111.2 (8)
C9—C10—C11122.74 (15)C1—N1—H1A129.5 (8)
C9—C10—H10118.6N1—N2—C7117.67 (13)
C6—C1—C2—C31.0 (3)C10—C11—C12—C13−179.58 (17)
N1—C1—C2—C3−178.25 (14)C11—C12—C13—C140.4 (3)
C1—C2—C3—C4−1.0 (3)C12—C13—C14—C15−0.9 (3)
C2—C3—C4—C50.2 (3)C13—C14—C15—C160.4 (3)
C2—C3—C4—C17179.13 (15)C14—C15—C16—C110.4 (2)
C3—C4—C5—C60.5 (3)C14—C15—C16—C7−179.87 (15)
C17—C4—C5—C6−178.43 (15)C12—C11—C16—C15−0.8 (2)
C4—C5—C6—C1−0.4 (3)C10—C11—C16—C15179.18 (14)
C2—C1—C6—C5−0.3 (2)C12—C11—C16—C7179.46 (14)
N1—C1—C6—C5178.88 (14)C10—C11—C16—C7−0.6 (2)
N2—C7—C8—O1−4.1 (2)N2—C7—C16—C154.2 (2)
C16—C7—C8—O1178.26 (13)C8—C7—C16—C15−178.03 (14)
N2—C7—C8—C9175.69 (14)N2—C7—C16—C11−176.08 (12)
C16—C7—C8—C9−1.9 (2)C8—C7—C16—C111.7 (2)
O1—C8—C9—C10−179.15 (15)C2—C1—N1—N2−176.56 (13)
C7—C8—C9—C101.0 (2)C6—C1—N1—N24.2 (2)
C8—C9—C10—C110.1 (3)C1—N1—N2—C7−176.60 (12)
C9—C10—C11—C12179.64 (16)C8—C7—N2—N13.5 (2)
C9—C10—C11—C16−0.3 (2)C16—C7—N2—N1−178.79 (12)
C16—C11—C12—C130.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O11.078 (16)1.578 (16)2.5414 (16)145.5 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HJ2006).

References

  • Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Lee, S. H., Kim, J. Y., Ko, J., Lee, J. Y. & Kim, J. S. (2004). J. Org. Chem.69, 2902–2905. [PubMed]
  • Oueslati, F., Dumazet-Bonnamour, I. & Lamartine, R. (2004). New J. Chem.28, 1575–1578.
  • Sheldrick, G. M. (1996). SADABS Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm.57, 77–86.

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