PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o2033.
Published online 2009 July 29. doi:  10.1107/S1600536809028438
PMCID: PMC2977113

1-(4-Cyano­phenyl­diazen-2-ium-1-yl)-2-naphtholate

Abstract

In the mol­ecule of the zwitterionic title compound, C17H11N3O, the naphthalene ring system is planar [maximum deviation = 0.029 (3) Å] and is oriented at a dihedral angle of 3.55 (3)° with respect to the benzene ring. An intra­molecular N—H(...)O hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, inter­molecular C—H(...)O inter­actions link the mol­ecules into centrosymmetric dimers.

Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 [triangle]); Oueslati et al. (2004 [triangle]). For a related structure, see: Rădulescu et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2033-scheme1.jpg

Experimental

Crystal data

  • C17H11N3O
  • M r = 273.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2033-efi1.jpg
  • a = 5.2673 (11) Å
  • b = 9.910 (2) Å
  • c = 25.239 (6) Å
  • β = 96.13 (3)°
  • V = 1309.9 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 294 K
  • 0.35 × 0.10 × 0.10 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.973, T max = 0.979
  • 13086 measured reflections
  • 2998 independent reflections
  • 1941 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.148
  • S = 1.02
  • 2998 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028438/hk2742sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028438/hk2742Isup2.hkl

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

supplementary crystallographic information

Comment

Azo compounds are characterized by the azo linkage (–N=N–) and are very important in the fields of dyes, pigments and advanced materials (Lee et al., 2004; Oueslati et al., 2004). We report herein the crystal structure of the title compound, obtained through the diazotization of 4-aminobenzonitrile followed by a coupling reaction with 2-naphthol.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C5/C10), B (C5-C10) and C (C11-C16) are, of course, planar, and they are oriented at dihedral angles of A/B = 2.32 (3), A/C = 2.58 (3) and B/C = 4.59 (3) °. The naphthalene ring system is planar with a maximum deviation of 0.029 (3) Å for atom C5. Intramolecular N-H···O hydrogen bond (Table 1) results in the formation of planar six-membered ring D (O1/N1/N2/C1/C2/H2A), which is oriented with respect to rings A, B and C at dihedral angles of A/D = 1.12 (3), B/D = 3.29 (3) and C/D = 1.47 (3) °. So, rings A, B, C and D are almost coplanar.

In the crystal structure, intermolecular C-H···O interactions link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared according to a literature method (Rădulescu et al., 2006). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement

H atoms were positioned geometrically with N-H = 0.86 Å (for NH) and C-H = 0.93 Å for aromatic H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Hydrogen bond is shown as dashed line.
Fig. 2.
A partial packing diagram. Hydrogen bonds are shown as dashed lines.

Crystal data

C17H11N3OF(000) = 568
Mr = 273.29Dx = 1.386 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1658 reflections
a = 5.2673 (11) Åθ = 3.2–28.9°
b = 9.910 (2) ŵ = 0.09 mm1
c = 25.239 (6) ÅT = 294 K
β = 96.13 (3)°Block, red
V = 1309.9 (5) Å30.35 × 0.10 × 0.10 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer2998 independent reflections
Radiation source: fine-focus sealed tube1941 reflections with I > 2σ(I)
graphiteRint = 0.059
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −12→12
Tmin = 0.973, Tmax = 0.979l = −32→32
13086 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0717P)2 + 0.0861P] where P = (Fo2 + 2Fc2)/3
2998 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.25 e Å3

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
O10.2630 (3)−0.03169 (14)0.45197 (5)0.0627 (4)
N10.3499 (3)0.15188 (14)0.36889 (6)0.0424 (4)
N20.5123 (3)0.16008 (14)0.41170 (5)0.0444 (4)
H2A0.49940.10720.43830.053*
N31.4464 (4)0.62761 (18)0.42541 (8)0.0731 (5)
C10.1628 (3)0.06230 (17)0.36607 (7)0.0427 (4)
C20.1200 (4)−0.03101 (18)0.40895 (7)0.0503 (5)
C3−0.0963 (4)−0.12070 (19)0.39970 (8)0.0576 (5)
H3A−0.1284−0.18210.42610.069*
C4−0.2519 (4)−0.11777 (18)0.35418 (8)0.0542 (5)
H4A−0.3884−0.17770.35010.065*
C5−0.2179 (3)−0.02633 (17)0.31131 (7)0.0456 (4)
C6−0.3895 (3)−0.02176 (19)0.26515 (7)0.0534 (5)
H6A−0.5266−0.08140.26140.064*
C7−0.3597 (4)0.0688 (2)0.22535 (7)0.0554 (5)
H7A−0.47600.07110.19490.066*
C8−0.1543 (4)0.15722 (19)0.23078 (7)0.0514 (5)
H8A−0.13290.21850.20370.062*
C90.0175 (3)0.15515 (18)0.27562 (7)0.0474 (4)
H9A0.15440.21490.27860.057*
C10−0.0106 (3)0.06409 (16)0.31707 (6)0.0410 (4)
C110.7076 (3)0.25635 (16)0.41359 (6)0.0398 (4)
C120.8755 (3)0.26618 (19)0.45927 (7)0.0505 (5)
H12A0.85790.20890.48780.061*
C131.0691 (4)0.36029 (19)0.46282 (7)0.0514 (5)
H13A1.18190.36660.49370.062*
C141.0948 (3)0.44545 (17)0.42018 (7)0.0446 (4)
C150.9273 (3)0.43388 (19)0.37409 (7)0.0509 (5)
H15A0.94560.49040.34530.061*
C160.7350 (3)0.33980 (18)0.37050 (7)0.0477 (4)
H16A0.62400.33210.33940.057*
C171.2921 (4)0.5465 (2)0.42332 (7)0.0533 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0707 (9)0.0608 (8)0.0547 (8)−0.0102 (7)−0.0025 (7)0.0170 (6)
N10.0445 (8)0.0398 (8)0.0427 (8)0.0009 (6)0.0035 (6)−0.0017 (6)
N20.0509 (9)0.0406 (8)0.0417 (8)−0.0023 (6)0.0044 (7)0.0056 (6)
N30.0691 (11)0.0661 (12)0.0849 (14)−0.0198 (10)0.0124 (10)−0.0066 (10)
C10.0452 (10)0.0373 (9)0.0464 (9)0.0016 (7)0.0087 (8)−0.0003 (7)
C20.0557 (11)0.0443 (10)0.0515 (11)0.0010 (8)0.0091 (9)0.0054 (8)
C30.0612 (12)0.0487 (11)0.0638 (12)−0.0088 (9)0.0104 (10)0.0127 (9)
C40.0503 (11)0.0446 (10)0.0680 (13)−0.0085 (8)0.0084 (10)0.0016 (9)
C50.0459 (10)0.0413 (10)0.0505 (10)−0.0009 (8)0.0100 (8)−0.0057 (8)
C60.0474 (10)0.0532 (11)0.0591 (12)−0.0049 (9)0.0031 (9)−0.0092 (9)
C70.0531 (11)0.0616 (12)0.0501 (11)0.0027 (10)−0.0005 (9)−0.0086 (9)
C80.0563 (11)0.0534 (11)0.0448 (10)0.0023 (9)0.0064 (9)−0.0002 (8)
C90.0486 (10)0.0461 (10)0.0481 (10)−0.0027 (8)0.0084 (8)−0.0017 (8)
C100.0426 (9)0.0376 (9)0.0436 (9)0.0025 (7)0.0087 (7)−0.0034 (7)
C110.0425 (9)0.0354 (9)0.0421 (9)0.0019 (7)0.0080 (7)−0.0002 (7)
C120.0621 (12)0.0494 (11)0.0392 (9)−0.0036 (9)0.0021 (9)0.0042 (8)
C130.0551 (11)0.0540 (11)0.0436 (10)−0.0057 (9)−0.0016 (8)−0.0025 (8)
C140.0435 (9)0.0422 (9)0.0488 (10)0.0004 (8)0.0090 (8)−0.0023 (8)
C150.0520 (11)0.0498 (10)0.0517 (10)−0.0005 (9)0.0088 (9)0.0122 (8)
C160.0483 (10)0.0505 (10)0.0429 (9)−0.0007 (8)−0.0007 (8)0.0074 (8)
C170.0523 (11)0.0541 (11)0.0543 (11)−0.0045 (9)0.0098 (9)−0.0034 (9)

Geometric parameters (Å, °)

O1—C21.254 (2)C7—C81.387 (3)
N1—N21.3072 (19)C7—H7A0.9300
N1—C11.323 (2)C8—C91.372 (2)
N2—C111.400 (2)C8—H8A0.9300
N2—H2A0.8600C9—C101.401 (2)
N3—C171.141 (2)C9—H9A0.9300
C1—C101.457 (2)C11—C121.380 (2)
C1—C21.459 (2)C11—C161.386 (2)
C2—C31.444 (3)C12—C131.378 (2)
C3—C41.338 (3)C12—H12A0.9300
C3—H3A0.9300C13—C141.386 (2)
C4—C51.437 (3)C13—H13A0.9300
C4—H4A0.9300C14—C151.387 (2)
C5—C61.397 (2)C14—C171.439 (3)
C5—C101.408 (2)C15—C161.373 (2)
C6—C71.369 (3)C15—H15A0.9300
C6—H6A0.9300C16—H16A0.9300
N2—N1—C1120.28 (14)C7—C8—H8A119.6
N1—N2—C11118.95 (14)C8—C9—C10120.83 (17)
N1—N2—H2A120.5C8—C9—H9A119.6
C11—N2—H2A120.5C10—C9—H9A119.6
N1—C1—C10115.69 (15)C9—C10—C5118.39 (16)
N1—C1—C2123.97 (16)C9—C10—C1122.33 (15)
C10—C1—C2120.31 (15)C5—C10—C1119.27 (15)
O1—C2—C3121.83 (17)C12—C11—C16120.16 (16)
O1—C2—C1121.30 (16)C12—C11—N2118.66 (15)
C3—C2—C1116.86 (17)C16—C11—N2121.18 (16)
C4—C3—C2121.70 (18)C13—C12—C11120.41 (16)
C4—C3—H3A119.1C13—C12—H12A119.8
C2—C3—H3A119.1C11—C12—H12A119.8
C3—C4—C5123.09 (17)C12—C13—C14119.67 (17)
C3—C4—H4A118.5C12—C13—H13A120.2
C5—C4—H4A118.5C14—C13—H13A120.2
C6—C5—C10119.42 (16)C13—C14—C15119.65 (16)
C6—C5—C4121.78 (16)C13—C14—C17120.72 (17)
C10—C5—C4118.76 (16)C15—C14—C17119.63 (16)
C7—C6—C5121.22 (17)C16—C15—C14120.67 (16)
C7—C6—H6A119.4C16—C15—H15A119.7
C5—C6—H6A119.4C14—C15—H15A119.7
C6—C7—C8119.42 (18)C15—C16—C11119.44 (16)
C6—C7—H7A120.3C15—C16—H16A120.3
C8—C7—H7A120.3C11—C16—H16A120.3
C9—C8—C7120.72 (18)N3—C17—C14179.1 (2)
C9—C8—H8A119.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.912.580 (2)133
C12—H12A···O1i0.932.453.362 (2)166

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2742).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • 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.
  • Rădulescu, C., Hossu, A. M. & Ioniţă, I. (2006). Dyes Pigments, 71, 123–129.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography