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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o218
https://doi.org/10.1107/S1600536807064549

1-(4-Methyl­phenyl­diazo­nium­yl)-2-naphtholate

Chuan-Ming Jin,a* Hao Li,a Zhen-Xing Zhonga and Ling-Yan Wua

aHubei Key Laboratory of Bioanalytic Techniques, Department of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China
*Correspondence e-mail: cmjin@email.hbnu.edu.cn

(Received 23 November 2007; accepted 29 November 2007; online 6 December 2007)

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[Lee, S. H., Kim, J. Y., Ko, J., Lee, J. Y. & Kim, J. S. (2004). J. Org. Chem. 69, 2902-2905.]); Oueslati et al. (2004[Oueslati, F., Dumazet-Bonnamour, I. & Lamartine, R. (2004). New J. Chem. 28, 1575-1578.]); Wang et al. (2003[Wang, M., Funabiki, K. & Matsui, M. (2003). Dyes Pigm. 57, 77-86.]).

[Scheme 1]

Experimental

Crystal data

  • C17H14N2O

  • Mr = 262.30

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.992

  • 14681 measured reflections

  • 2913 independent reflections

  • 1802 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O1 1.078 (16) 1.578 (16) 2.5414 (16) 145.5 (12)

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2001[Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS, Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064549/hj2006Isup2.hkl

checkCIF report


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Structure description top

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).

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

Computing details top

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

Figures top
[Figure 1] 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.
-(4-Methylphenyldiazoniumyl)-2-naphtholate top
Crystal data top
C17H14N2OF(000) = 552
Mr = 262.30Dx = 1.299 Mg m−3
Monoclinic, P21/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 = 3.0–23.4°
c = 7.1430 (2) ŵ = 0.08 mm−1
β = 95.752 (2)°T = 293 K
V = 1341.11 (7) Å3Needle, red
Z = 40.20 × 0.10 × 0.10 mm
Data collection top
Bruker SMART Apex CCD area detector
diffractometer		2913 independent reflections
Radiation source: fine-focus sealed tube1802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
phi and ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.984, Tmax = 0.992k = −17→16
14681 measured reflectionsl = −9→9
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0816P)2]
where P = (Fo2 + 2Fc2)/3
2913 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C17H14N2OV = 1341.11 (7) Å3
Mr = 262.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.6740 (4) ŵ = 0.08 mm−1
b = 13.8000 (4) ÅT = 293 K
c = 7.1430 (2) Å0.20 × 0.10 × 0.10 mm
β = 95.752 (2)°
Data collection top
Bruker SMART Apex CCD area detector
diffractometer		2913 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1802 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.992Rint = 0.033
14681 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å−3
2913 reflectionsΔρmin = −0.20 e Å−3
185 parameters
Special details top

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

Experimental details

Crystal data
Chemical formulaC17H14N2O
Mr262.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.6740 (4), 13.8000 (4), 7.1430 (2)
β (°) 95.752 (2)
V (Å3)1341.11 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART Apex CCD area detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.984, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections		14681, 2913, 1802
Rint0.033
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.149, 1.04
No. of reflections2913
No. of parameters185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.18, −0.20

Computer programs: SMART, (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O11.078 (16)1.578 (16)2.5414 (16)145.5 (12)
 

Acknowledgements

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).

References

First citationBruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLee, S. H., Kim, J. Y., Ko, J., Lee, J. Y. & Kim, J. S. (2004). J. Org. Chem. 69, 2902–2905.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationOueslati, F., Dumazet-Bonnamour, I. & Lamartine, R. (2004). New J. Chem. 28, 1575–1578.  Web of Science CrossRef CAS Google Scholar
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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o218
https://doi.org/10.1107/S1600536807064549
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