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The title mol­ecule, C21H19N3O2, lies on a crystallographic twofold axis which runs through the central C and N atoms of the pyridine ring. The aryl rings are slightly twisted out of the pyridine-ring plane by an angle of 15.7 (14)°. Molecules are linked by N—H...O intermolecular hydrogen bonds to form chains in the c direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004604/lh6033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004604/lh6033Isup2.hkl
Contains datablock I

CCDC reference: 209917

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.089
  • wR factor = 0.181
  • Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.137
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Our research has shown that the previously reported ligands (II) and (III) (Qi et al., 2001; Yang et al., 2001) easily form CoIII complexes via the coordination of the pyridine N and the amide N atoms. However, these CoIII complexes are difficult to crystallize and this may be due to the steric effect of the bulky naphthyl ring of ligand (II) or the 2-methoxy group on the phenyl ring of ligand (III). Therefore, ligand (I), with less steric hindrance of the coordinated amide N atom, was prepared. We expect that it will be easier to form metal complexes of this ligand and grow single crystals for X-ray analysis.

Compound (I) has the similar plane structures to those in (II) and (III). The two phenyl rings are twisted from coplanarity with the pyridine-ring plane and form dihedral angles of 15.7 (14)°. The dihedral angle between the two phenyl rings is 25.0 (15)°. Intermolecular N—H···O, hydrogen bonds, formed via the carbonyl O and amide H atoms, link molecules into chains in the c direction (see Table 1).

Experimental top

The title compound was synthesized from 2,6-pyridinedicarboxylic acid and 4-toluidine by following a published procedure (Ray et al., 1997). The crystal used for the data collection was obtained by slow evaporation from a dimethylformamide/water saturated solution at room temperature.

Refinement top

The H atoms were placed in their geometrically calculated positions and included in the final refinement in the riding-model approximation. The percentage of observed data, collected by our diffractometer, was only 35% of the unique data available to a θmax of 27.5°. Inclusion of such a high percentage of essentially unobserved data into the structure refinement restricts the precision of the results. The weak data also leads to a high value of Rint of 0.137.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing ellipsoids at the 30% probability level (Siemens, 1995). The unlabeled part of the molecule is related to the labeled part by the symmetry code (-x, y, −z + 1/2).
[Figure 2] Fig. 2. The molecular packing, showing the hydrogen bonding (dashed lines) in the c direction.
N,N'-Di-4-methylphenylpyridine-2,6-dicarboxamide top
Crystal data top
C21H19N3O2F(000) = 728
Mr = 345.39Dx = 1.251 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2125 reflections
a = 25.140 (5) Åθ = 1–27.5°
b = 8.5779 (17) ŵ = 0.08 mm1
c = 8.5295 (17) ÅT = 294 K
β = 94.46 (3)°Prism, yellow
V = 1833.8 (6) Å30.22 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
2084 independent reflections
Radiation source: fine-focus sealed tube734 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.137
ϕ and ω scansθmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3225
Tmin = 0.982, Tmax = 0.992k = 1011
5712 measured reflectionsl = 1111
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.089H-atom parameters constrained
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2084 reflectionsΔρmax = 0.22 e Å3
120 parametersΔρmin = 0.25 e Å3
Crystal data top
C21H19N3O2V = 1833.8 (6) Å3
Mr = 345.39Z = 4
Monoclinic, C2/cMo Kα radiation
a = 25.140 (5) ŵ = 0.08 mm1
b = 8.5779 (17) ÅT = 294 K
c = 8.5295 (17) Å0.22 × 0.20 × 0.10 mm
β = 94.46 (3)°
Data collection top
Bruker CCD area-detector
diffractometer
2084 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
734 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.992Rint = 0.137
5712 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0890 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.02Δρmax = 0.22 e Å3
2084 reflectionsΔρmin = 0.25 e Å3
120 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
O10.07266 (11)0.1728 (3)0.0835 (3)0.0712 (9)
N10.07286 (11)0.0329 (3)0.0855 (3)0.0479 (8)
H10.05860.06560.16780.058*
N20.00000.1195 (4)0.25000.0437 (10)
C10.21858 (19)0.4737 (6)0.1486 (6)0.130 (2)
H1A0.24690.48730.06740.195*
H1B0.23290.43250.24110.195*
H1C0.20200.57250.17280.195*
C20.17732 (17)0.3609 (6)0.0922 (5)0.0796 (14)
C30.17786 (18)0.2080 (6)0.1422 (5)0.0873 (15)
H30.20180.17910.21480.105*
C40.14395 (15)0.0954 (5)0.0882 (4)0.0675 (12)
H40.14560.00710.12280.081*
C50.10785 (13)0.1386 (4)0.0178 (4)0.0466 (9)
C60.10708 (15)0.2910 (5)0.0688 (4)0.0638 (11)
H60.08360.32110.14210.077*
C70.14110 (17)0.3980 (5)0.0112 (5)0.0791 (14)
H70.13920.50090.04460.095*
C80.05902 (14)0.1121 (4)0.0376 (4)0.0479 (9)
C90.02741 (13)0.2001 (4)0.1502 (4)0.0426 (9)
C100.02767 (14)0.3605 (4)0.1440 (4)0.0569 (10)
H100.04620.41260.06970.068*
C110.00000.4418 (6)0.25000.080 (2)
H110.00000.55030.25000.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.117 (2)0.0570 (17)0.0430 (16)0.0104 (13)0.0277 (16)0.0098 (12)
N10.068 (2)0.0464 (18)0.0313 (17)0.0017 (14)0.0145 (16)0.0002 (13)
N20.052 (3)0.044 (2)0.035 (2)0.0000.001 (2)0.000
C10.104 (4)0.175 (5)0.111 (5)0.053 (4)0.003 (4)0.065 (4)
C20.059 (3)0.115 (4)0.063 (3)0.019 (3)0.006 (2)0.041 (3)
C30.066 (3)0.142 (4)0.056 (3)0.002 (3)0.021 (2)0.023 (3)
C40.055 (3)0.095 (3)0.054 (3)0.001 (2)0.018 (2)0.007 (2)
C50.044 (2)0.062 (3)0.034 (2)0.0009 (17)0.0055 (18)0.0124 (18)
C60.063 (3)0.066 (3)0.065 (3)0.007 (2)0.023 (2)0.002 (2)
C70.083 (4)0.073 (3)0.083 (4)0.010 (2)0.020 (3)0.024 (2)
C80.060 (2)0.045 (2)0.039 (2)0.0084 (18)0.0027 (19)0.0040 (18)
C90.059 (2)0.042 (2)0.0253 (18)0.0063 (17)0.0073 (17)0.0017 (16)
C100.087 (3)0.037 (2)0.047 (2)0.0024 (18)0.005 (2)0.0042 (18)
C110.137 (6)0.026 (3)0.078 (5)0.0000.010 (4)0.000
Geometric parameters (Å, º) top
O1—C81.229 (3)C3—H30.9300
N1—C81.346 (4)C4—C51.380 (4)
N1—C51.417 (4)C4—H40.9300
N1—H10.8600C5—C61.378 (4)
N2—C9i1.330 (3)C6—C71.372 (5)
N2—C91.330 (3)C6—H60.9300
C1—C21.524 (5)C7—H70.9300
C1—H1A0.9600C8—C91.497 (4)
C1—H1B0.9600C9—C101.377 (4)
C1—H1C0.9600C10—C111.373 (4)
C2—C71.353 (5)C10—H100.9300
C2—C31.380 (5)C11—C10i1.373 (4)
C3—C41.390 (5)C11—H110.9300
C8—N1—C5128.4 (3)C6—C5—N1117.0 (3)
C8—N1—H1115.8C4—C5—N1123.8 (4)
C5—N1—H1115.8C7—C6—C5119.8 (3)
C9i—N2—C9117.3 (4)C7—C6—H6120.1
C2—C1—H1A109.5C5—C6—H6120.1
C2—C1—H1B109.5C2—C7—C6123.1 (4)
H1A—C1—H1B109.5C2—C7—H7118.5
C2—C1—H1C109.5C6—C7—H7118.5
H1A—C1—H1C109.5O1—C8—N1124.3 (3)
H1B—C1—H1C109.5O1—C8—C9121.5 (3)
C7—C2—C3116.6 (4)N1—C8—C9114.1 (3)
C7—C2—C1124.4 (5)N2—C9—C10123.2 (3)
C3—C2—C1118.9 (4)N2—C9—C8118.4 (3)
C2—C3—C4122.4 (4)C10—C9—C8118.3 (3)
C2—C3—H3118.8C11—C10—C9118.6 (4)
C4—C3—H3118.8C11—C10—H10120.7
C5—C4—C3118.8 (4)C9—C10—H10120.7
C5—C4—H4120.6C10—C11—C10i118.9 (5)
C3—C4—H4120.6C10—C11—H11120.5
C6—C5—C4119.2 (3)C10i—C11—H11120.5
C7—C2—C3—C41.3 (6)C5—N1—C8—O15.3 (6)
C1—C2—C3—C4175.6 (4)C5—N1—C8—C9171.4 (3)
C2—C3—C4—C51.0 (6)C9i—N2—C9—C101.3 (2)
C3—C4—C5—C61.1 (5)C9i—N2—C9—C8179.4 (3)
C3—C4—C5—N1177.4 (4)O1—C8—C9—N2159.4 (3)
C8—N1—C5—C6167.0 (4)N1—C8—C9—N223.9 (4)
C8—N1—C5—C416.6 (5)O1—C8—C9—C1019.9 (5)
C4—C5—C6—C71.6 (5)N1—C8—C9—C10156.9 (3)
N1—C5—C6—C7178.1 (3)N2—C9—C10—C112.6 (5)
C3—C2—C7—C61.7 (6)C8—C9—C10—C11178.2 (3)
C1—C2—C7—C6175.0 (4)C9—C10—C11—C10i1.2 (2)
C5—C6—C7—C22.0 (6)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.862.313.068 (4)147
Symmetry code: (ii) x, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC21H19N3O2
Mr345.39
Crystal system, space groupMonoclinic, C2/c
Temperature (K)294
a, b, c (Å)25.140 (5), 8.5779 (17), 8.5295 (17)
β (°) 94.46 (3)
V3)1833.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.22 × 0.20 × 0.10
Data collection
DiffractometerBruker CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
5712, 2084, 734
Rint0.137
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.089, 0.181, 1.02
No. of reflections2084
No. of parameters120
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.25

Computer programs: SMART (Siemens, 1995), SMART, SHELXTL-NT (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-NT.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.313.068 (4)147
Symmetry code: (i) x, y, z+1/2.
 

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