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

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ISSN: 2056-9890

N,N′-(Pyridine-2,6-di­yl)dibenzamide

aSama Technical and Vocational Training College, Islamic Azad University, Mamaghan Branch, Mamaghan, Iran, bDepartment of Chemistry, University of Zanjan, 45195-313 Zanjan, Iran, and cChemistry Department, The University of Warsaw, Pasteura 1, 02093 Warszawa, Poland
*Correspondence e-mail: nadernoshiranzadeh@yahoo.com

(Received 5 December 2012; accepted 8 December 2012; online 19 December 2012)

The mol­ecule of the title compound, C19H15N3O2, is completed by the application of crystallographic twofold symmetry, with the pyridine N atom lying on the rotation axis. The mol­ecular structure is approximately planar, the dihedral angle between the mean planes of the pyridine and benzene rings being 7.53 (11)°. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into a two-dimensional array perpendicular to the c axis.

Related literature

For metal complexes of carboxamide ligands, see: Adolph et al. (2012[Adolph, M., Zevaco, T. A., Walter, O., Dinjus, E. & Döring, M. (2012). Polyhedron, 48, 92-98.]); Amiri et al. (2009[Amiri, A., Amirnasr, M., Meghdadi, S., Mereiter, K., Ghodsi, V. & Gholami, A. (2009). Inorg. Chim. Acta, 362, 3934-3940.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O2

  • Mr = 317.34

  • Tetragonal, P 41 21 2

  • a = 5.0314 (1) Å

  • c = 58.701 (3) Å

  • V = 1486.02 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.21 × 0.09 × 0.02 mm

Data collection
  • Oxford Diffraction Xcalibur Opal diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.986, Tmax = 1.000

  • 1298 measured reflections

  • 16463 independent reflections

  • 1168 reflections with I > 2σ(I)

  • Rint = 0.065

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.090

  • S = 1.23

  • 1298 reflections

  • 112 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.86 2.25 3.030 (2) 151
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2006[Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Carboxamides are compounds which are prepared by the reaction of amines and acylhalides. They are important N,O-donor ligands and have widespread applications in fields such as in coordination chemistry (Adolph et al. 2012 & Amiri et al. 2009). As biologically active compounds, carboxamides find application in the treatment of diseases such as cancer, rheumatic disorders and inhibitors of calpain (calcium dependant cysteine proteases).

The molecular structure of the title compound is shown in Fig. 1. The molecule is approximately planar with the dihedral angle between the mean planes of the pyridine and benzene rings being 7.53 (11)°. Intermolecular N—H···O hydrogen bonds, with the carbonyl-O atoms acting as acceptors, link molecules into a two-dimensional array perpendicular to the c axis as illustrated in Fig. 2.

Related literature top

For metal complexes of carboxamide ligands, see: Adolph et al. (2012); Amiri et al. (2009).

Experimental top

All reagents were commercially available and used as received. To a magnetically stirred solution of 2,6-diaminopyridine (0.109 g, 1 mmol) and triethylamine (0.277 ml, 2 mmol) in dichloromethane (5 ml) was added drop-wise a mixture of benzoyl chloride (0.232 ml, 2 mmol) in dichloromethane (2 ml) at -10 °C over 15 min. The mixture was allowed to warm to room temperature and stirred for 48 h at room temperature. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel; petroleum ether-ethyl acetate) to give the title compound as a yellow powder. Crystals of the title compound were obtained from its methanol solution by slow solvent evaporation. Yield: 85%. Melting point: 407–408 K. Selected IR (KBr, cm-1): 3245 (N—H), 3061 (C—H), 1653 (COamide), 1584 (CN), 1461 (CC).

Refinement top

The hydrogen atom of the N—H group was positioned geometrically and refined as a riding atoms with N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(N). The C—H hydrogen atoms were positioned geometrically and refined as riding atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis CCD (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 50% probability level. The molecule has twofold symmetry and the unlabelled atoms are related by the symmetry operation y, x, -z.
[Figure 2] Fig. 2. Hydrogen bonding in the title compound leading to supramolecular layers in the ab plane. The green dashed lines indicate N—H···O hydrogen bonds.
N,N'-(Pyridine-2,6-diyl)dibenzamide top
Crystal data top
C19H15N3O2Dx = 1.418 Mg m3
Mr = 317.34Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 3266 reflections
Hall symbol: P 4abw 2nwθ = 1.7–28.5°
a = 5.0314 (1) ŵ = 0.10 mm1
c = 58.701 (3) ÅT = 100 K
V = 1486.02 (8) Å3Block, yellow
Z = 40.21 × 0.09 × 0.02 mm
F(000) = 664
Data collection top
Oxford Diffraction Xcalibur Opal
diffractometer
1298 independent reflections
Radiation source: fine-focus sealed tube1168 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 8.4441 pixels mm-1θmax = 24.9°, θmin = 2.8°
ω scanh = 05
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)
k = 04
Tmin = 0.986, Tmax = 1.000l = 6468
16463 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.P)2 + 0.9748P]
where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max < 0.001
1298 reflectionsΔρmax = 0.18 e Å3
112 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0091 (16)
Crystal data top
C19H15N3O2Z = 4
Mr = 317.34Mo Kα radiation
Tetragonal, P41212µ = 0.10 mm1
a = 5.0314 (1) ÅT = 100 K
c = 58.701 (3) Å0.21 × 0.09 × 0.02 mm
V = 1486.02 (8) Å3
Data collection top
Oxford Diffraction Xcalibur Opal
diffractometer
1298 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)
1168 reflections with I > 2σ(I)
Tmin = 0.986, Tmax = 1.000Rint = 0.065
16463 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.23Δρmax = 0.18 e Å3
1298 reflectionsΔρmin = 0.16 e Å3
112 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
O11.3618 (3)0.6195 (3)0.04884 (3)0.0204 (4)
N10.8073 (4)0.8073 (4)0.00000.0135 (6)
N20.9407 (4)0.6428 (4)0.03476 (3)0.0143 (5)
H20.78190.58190.03620.017*
C71.0307 (5)0.3655 (5)0.06778 (4)0.0144 (5)
C50.9853 (5)0.8265 (5)0.01690 (3)0.0138 (5)
C80.8160 (5)0.1943 (5)0.06481 (4)0.0171 (5)
H80.71800.19970.05140.020*
C31.1969 (5)1.1969 (5)0.00000.0159 (7)
H31.32761.32760.00000.019*
C61.1258 (5)0.5538 (5)0.04983 (4)0.0143 (5)
C121.1738 (5)0.3566 (5)0.08806 (4)0.0168 (5)
H121.31870.46900.09010.020*
C41.1857 (5)1.0149 (5)0.01758 (4)0.0154 (5)
H41.30821.01880.02940.018*
C111.1026 (5)0.1821 (5)0.10523 (4)0.0210 (6)
H111.19670.18020.11890.025*
C90.7480 (5)0.0157 (5)0.08184 (4)0.0186 (6)
H90.60660.10070.07970.022*
C100.8902 (5)0.0100 (5)0.10204 (4)0.0200 (6)
H100.84340.10910.11350.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0118 (9)0.0265 (10)0.0231 (9)0.0002 (7)0.0012 (7)0.0046 (8)
N10.0144 (9)0.0144 (9)0.0118 (13)0.0035 (12)0.0000 (8)0.0000 (8)
N20.0115 (11)0.0178 (11)0.0135 (9)0.0022 (9)0.0010 (8)0.0016 (8)
C70.0149 (12)0.0137 (12)0.0147 (12)0.0023 (10)0.0005 (10)0.0025 (10)
C50.0164 (12)0.0140 (13)0.0110 (11)0.0045 (10)0.0008 (10)0.0007 (9)
C80.0165 (13)0.0180 (13)0.0167 (12)0.0031 (11)0.0013 (10)0.0004 (10)
C30.0157 (11)0.0157 (11)0.0162 (17)0.0016 (14)0.0011 (10)0.0011 (10)
C60.0175 (13)0.0160 (13)0.0094 (11)0.0022 (10)0.0003 (10)0.0033 (9)
C120.0197 (13)0.0164 (13)0.0143 (11)0.0016 (11)0.0006 (10)0.0013 (10)
C40.0144 (13)0.0181 (13)0.0136 (11)0.0018 (10)0.0018 (10)0.0024 (10)
C110.0262 (14)0.0210 (14)0.0158 (12)0.0011 (11)0.0039 (10)0.0007 (11)
C90.0175 (13)0.0173 (13)0.0211 (12)0.0003 (11)0.0018 (11)0.0015 (10)
C100.0254 (14)0.0162 (13)0.0184 (12)0.0024 (11)0.0062 (11)0.0038 (11)
Geometric parameters (Å, º) top
O1—C61.234 (3)C3—C4i1.381 (3)
N1—C51.340 (3)C3—C41.381 (3)
N1—C5i1.340 (3)C3—H30.9300
N2—C61.360 (3)C12—C111.384 (3)
N2—C51.415 (3)C12—H120.9300
N2—H20.8600C4—H40.9300
C7—C121.392 (3)C11—C101.388 (3)
C7—C81.393 (3)C11—H110.9300
C7—C61.496 (3)C9—C101.385 (3)
C5—C41.385 (3)C9—H90.9300
C8—C91.387 (3)C10—H100.9300
C8—H80.9300
C5—N1—C5i116.9 (3)O1—C6—C7120.7 (2)
C6—N2—C5126.0 (2)N2—C6—C7116.6 (2)
C6—N2—H2117.0C11—C12—C7120.6 (2)
C5—N2—H2117.0C11—C12—H12119.7
C12—C7—C8119.2 (2)C7—C12—H12119.7
C12—C7—C6117.2 (2)C3—C4—C5117.5 (2)
C8—C7—C6123.5 (2)C3—C4—H4121.2
N1—C5—C4123.9 (2)C5—C4—H4121.2
N1—C5—N2113.3 (2)C12—C11—C10119.8 (2)
C4—C5—N2122.8 (2)C12—C11—H11120.1
C9—C8—C7120.1 (2)C10—C11—H11120.1
C9—C8—H8119.9C10—C9—C8120.2 (2)
C7—C8—H8119.9C10—C9—H9119.9
C4i—C3—C4120.3 (3)C8—C9—H9119.9
C4i—C3—H3119.9C9—C10—C11120.0 (2)
C4—C3—H3119.9C9—C10—H10120.0
O1—C6—N2122.7 (2)C11—C10—H10120.0
C5i—N1—C5—C40.84 (17)C8—C7—C6—N228.4 (3)
C5i—N1—C5—N2176.1 (2)C8—C7—C12—C110.7 (4)
C6—N2—C5—N1156.80 (19)C6—C7—C12—C11178.2 (2)
C6—N2—C5—C426.3 (3)C4i—C3—C4—C50.75 (15)
C12—C7—C8—C90.6 (3)N1—C5—C4—C31.6 (3)
C6—C7—C8—C9176.7 (2)N2—C5—C4—C3174.99 (17)
C5—N2—C6—O12.8 (4)C7—C12—C11—C101.5 (4)
C5—N2—C6—C7178.16 (19)C7—C8—C9—C101.2 (3)
C12—C7—C6—O126.8 (3)C8—C9—C10—C110.4 (4)
C8—C7—C6—O1150.6 (2)C12—C11—C10—C90.9 (4)
C12—C7—C6—N2154.2 (2)
Symmetry code: (i) y, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1ii0.862.253.030 (2)151
Symmetry code: (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC19H15N3O2
Mr317.34
Crystal system, space groupTetragonal, P41212
Temperature (K)100
a, c (Å)5.0314 (1), 58.701 (3)
V3)1486.02 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.21 × 0.09 × 0.02
Data collection
DiffractometerOxford Diffraction Xcalibur Opal
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2010)
Tmin, Tmax0.986, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
16463, 1298, 1168
Rint0.065
(sin θ/λ)max1)0.593
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.090, 1.23
No. of reflections1298
No. of parameters112
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.253.030 (2)151.2
Symmetry code: (i) x1, y, z.
 

Footnotes

Additional correspondence author, e-mail: mahboubi_p@yahoo.com.

Acknowledgements

The authors are grateful to the University of Zanjan, Islamic Azad University (Mamagghan Branch) and the University of Warsaw for financial support.

References

First citationAdolph, M., Zevaco, T. A., Walter, O., Dinjus, E. & Döring, M. (2012). Polyhedron, 48, 92–98.  Web of Science CSD CrossRef CAS
First citationAmiri, A., Amirnasr, M., Meghdadi, S., Mereiter, K., Ghodsi, V. & Gholami, A. (2009). Inorg. Chim. Acta, 362, 3934–3940.  Web of Science CSD CrossRef CAS
First citationBrandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationOxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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