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In the title tridentate ligand, C21H19N3O4, the phenyl rings are slightly twisted out of the pyridine-ring plane. C—H...O intramolecular and intermolecular hydrogen bonds are observed in the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018694/ci6065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018694/ci6065Isup2.hkl
Contains datablock I

CCDC reference: 177202

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.041
  • wR factor = 0.104
  • Data-to-parameter ratio = 10.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.53 From the CIF: _reflns_number_total 2571 Count of symmetry unique reflns 2579 Completeness (_total/calc) 99.69% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N,N'-Di-2-methoxyphenylpyridine-2,6-dicarboxamide top
Crystal data top
C21H19N3O4Dx = 1.314 Mg m3
Mr = 377.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4522 reflections
a = 4.7919 (9) Åθ = 1–27.5°
b = 15.775 (3) ŵ = 0.09 mm1
c = 25.228 (5) ÅT = 294 K
V = 1907.1 (6) Å3Plate, colourless
Z = 40.24 × 0.20 × 0.18 mm
F(000) = 792
Data collection top
Siemens CCD area-detector
diffractometer
2571 independent reflections
Radiation source: fine-focus sealed tube1007 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
Detector resolution: 8.3 pixels mm-1θmax = 27.5°, θmin = 2.1°
ω scansh = 65
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 2019
Tmin = 0.978, Tmax = 0.984l = 2932
12538 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max < 0.001
2571 reflectionsΔρmax = 0.14 e Å3
253 parametersΔρmin = 0.20 e Å3
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
O10.3689 (8)0.20900 (18)0.25572 (11)0.1129 (13)
O21.0181 (7)0.02251 (16)0.23433 (10)0.0797 (8)
O31.1365 (7)0.10741 (15)0.48373 (10)0.0982 (11)
O41.0396 (6)0.11966 (15)0.36016 (9)0.0738 (8)
N10.7888 (6)0.13141 (16)0.36080 (11)0.0543 (8)
N20.6785 (7)0.10072 (17)0.25762 (10)0.0636 (9)
H2A0.78900.07410.27870.076*
N31.1108 (7)0.01954 (17)0.41213 (10)0.0630 (9)
H3A1.04910.01710.38010.076*
C11.2034 (10)0.0912 (2)0.22548 (16)0.0900 (15)
H1B1.30660.10250.25730.135*
H1C1.33040.07690.19740.135*
H1D1.09850.14060.21570.135*
C20.8516 (9)0.0033 (3)0.19318 (16)0.0662 (11)
C30.8550 (10)0.0318 (2)0.14311 (18)0.0794 (14)
H3B0.97650.07580.13500.095*
C40.6727 (12)0.0001 (3)0.10503 (18)0.0898 (17)
H4A0.67460.02310.07110.108*
C50.4911 (11)0.0645 (3)0.11623 (16)0.0862 (15)
H5A0.36900.08460.09050.103*
C60.4926 (10)0.0994 (2)0.16694 (15)0.0725 (12)
H6A0.37110.14350.17500.087*
C70.6699 (9)0.0697 (2)0.20503 (14)0.0591 (11)
C80.5389 (10)0.1658 (2)0.27928 (15)0.0675 (12)
C90.6133 (9)0.1839 (2)0.33589 (14)0.0582 (11)
C100.5008 (9)0.2547 (2)0.35993 (15)0.0725 (12)
H10A0.37450.28900.34190.087*
C110.5789 (10)0.2738 (2)0.41112 (15)0.0801 (13)
H11A0.50920.32190.42780.096*
C120.7589 (10)0.2216 (2)0.43699 (14)0.0742 (13)
H12A0.81290.23310.47170.089*
C130.8609 (9)0.1505 (2)0.41071 (14)0.0589 (11)
C141.0511 (9)0.0906 (2)0.43950 (15)0.0642 (11)
C151.2627 (8)0.0510 (2)0.43016 (13)0.0539 (10)
C161.4442 (9)0.0510 (2)0.47177 (14)0.0701 (12)
H16A1.47460.00130.49070.084*
C171.5841 (9)0.1246 (3)0.48614 (15)0.0755 (12)
H17A1.70640.12430.51480.091*
C181.5413 (9)0.1976 (2)0.45809 (15)0.0731 (12)
H18A1.63580.24680.46760.088*
C191.3606 (9)0.1988 (2)0.41614 (14)0.0665 (11)
H19A1.33150.24880.39750.080*
C201.2214 (8)0.1260 (2)0.40137 (13)0.0565 (10)
C210.9571 (11)0.1966 (2)0.33382 (14)0.0881 (15)
H21B0.82910.18340.30570.132*
H21C0.86800.23370.35880.132*
H21A1.11890.22400.31940.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.161 (3)0.093 (2)0.084 (2)0.064 (3)0.041 (2)0.0022 (17)
O20.082 (2)0.0748 (18)0.082 (2)0.0167 (19)0.0105 (18)0.0082 (15)
O30.155 (3)0.0761 (17)0.0634 (17)0.027 (2)0.036 (2)0.0266 (15)
O40.093 (2)0.0621 (15)0.0660 (16)0.0006 (17)0.0252 (16)0.0161 (13)
N10.069 (2)0.0438 (16)0.0495 (18)0.0060 (18)0.0004 (16)0.0019 (15)
N20.087 (3)0.0550 (18)0.0489 (19)0.013 (2)0.0097 (18)0.0037 (16)
N30.087 (3)0.0553 (18)0.0465 (18)0.005 (2)0.0158 (17)0.0090 (15)
C10.080 (3)0.064 (3)0.126 (4)0.014 (3)0.025 (3)0.001 (2)
C20.072 (3)0.064 (3)0.063 (3)0.012 (3)0.008 (3)0.003 (2)
C30.101 (4)0.069 (3)0.068 (3)0.026 (3)0.034 (3)0.013 (3)
C40.129 (5)0.085 (3)0.055 (3)0.049 (4)0.017 (3)0.002 (3)
C50.118 (4)0.084 (3)0.057 (3)0.035 (4)0.005 (3)0.008 (2)
C60.094 (4)0.060 (2)0.063 (3)0.010 (3)0.013 (3)0.011 (2)
C70.076 (3)0.052 (2)0.049 (2)0.006 (2)0.002 (2)0.0013 (19)
C80.090 (4)0.047 (2)0.065 (3)0.012 (3)0.001 (3)0.001 (2)
C90.076 (3)0.044 (2)0.055 (2)0.001 (2)0.004 (2)0.0013 (19)
C100.093 (4)0.053 (2)0.072 (3)0.021 (3)0.007 (3)0.004 (2)
C110.116 (4)0.058 (2)0.066 (3)0.019 (3)0.008 (3)0.012 (2)
C120.111 (4)0.052 (2)0.060 (3)0.004 (3)0.004 (3)0.007 (2)
C130.081 (3)0.044 (2)0.052 (2)0.002 (2)0.001 (2)0.0060 (19)
C140.084 (3)0.057 (2)0.051 (2)0.005 (3)0.006 (2)0.009 (2)
C150.062 (3)0.053 (2)0.048 (2)0.002 (2)0.008 (2)0.0011 (19)
C160.082 (3)0.067 (2)0.061 (2)0.001 (3)0.020 (2)0.009 (2)
C170.075 (3)0.085 (3)0.067 (3)0.006 (3)0.018 (2)0.007 (2)
C180.083 (3)0.067 (3)0.069 (3)0.012 (3)0.005 (3)0.003 (2)
C190.073 (3)0.060 (3)0.067 (3)0.003 (3)0.000 (2)0.001 (2)
C200.064 (3)0.057 (2)0.048 (2)0.002 (2)0.005 (2)0.002 (2)
C210.100 (4)0.081 (3)0.083 (3)0.028 (3)0.011 (3)0.029 (2)
Geometric parameters (Å, º) top
O1—C81.217 (4)C4—C51.368 (6)
O2—C21.371 (4)C5—C61.393 (5)
O2—C11.418 (4)C6—C71.366 (5)
O3—C141.218 (4)C8—C91.499 (5)
O4—C201.360 (4)C9—C101.381 (4)
O4—C211.439 (4)C10—C111.378 (5)
N1—C91.337 (4)C11—C121.360 (5)
N1—C131.340 (4)C12—C131.391 (4)
N2—C81.342 (4)C13—C141.500 (5)
N2—C71.415 (4)C15—C161.363 (4)
N3—C141.348 (4)C15—C201.402 (4)
N3—C151.405 (4)C16—C171.390 (5)
C2—C31.379 (5)C17—C181.367 (4)
C2—C71.394 (5)C18—C191.368 (5)
C3—C41.392 (5)C19—C201.380 (5)
C2—O2—C1118.2 (3)C10—C9—C8118.7 (4)
C20—O4—C21117.9 (3)C11—C10—C9118.8 (4)
C9—N1—C13117.7 (3)C12—C11—C10119.4 (4)
C8—N2—C7129.2 (3)C11—C12—C13118.8 (4)
C14—N3—C15127.1 (3)N1—C13—C12122.6 (4)
O2—C2—C3124.5 (4)N1—C13—C14118.0 (3)
O2—C2—C7115.1 (4)C12—C13—C14119.3 (3)
C3—C2—C7120.3 (4)O3—C14—N3125.4 (4)
C2—C3—C4118.7 (4)O3—C14—C13120.7 (3)
C5—C4—C3121.7 (4)N3—C14—C13113.9 (3)
C4—C5—C6118.7 (5)C16—C15—C20119.3 (4)
C7—C6—C5120.9 (4)C16—C15—N3125.5 (3)
C6—C7—C2119.7 (4)C20—C15—N3115.3 (3)
C6—C7—N2124.0 (4)C15—C16—C17120.6 (4)
C2—C7—N2116.3 (4)C18—C17—C16119.8 (4)
O1—C8—N2124.3 (4)C17—C18—C19120.4 (4)
O1—C8—C9121.1 (4)C18—C19—C20120.3 (4)
N2—C8—C9114.6 (4)O4—C20—C19125.2 (3)
N1—C9—C10122.7 (3)O4—C20—C15115.1 (3)
N1—C9—C8118.6 (3)C19—C20—C15119.6 (4)
C1—O2—C2—C31.3 (5)C10—C11—C12—C130.5 (6)
C1—O2—C2—C7178.5 (3)C9—N1—C13—C120.5 (5)
O2—C2—C3—C4179.4 (3)C9—N1—C13—C14178.3 (3)
C7—C2—C3—C40.3 (5)C11—C12—C13—N10.0 (6)
C2—C3—C4—C50.4 (6)C11—C12—C13—C14177.7 (4)
C3—C4—C5—C60.8 (6)C15—N3—C14—O35.1 (7)
C4—C5—C6—C70.5 (6)C15—N3—C14—C13174.3 (3)
C5—C6—C7—C20.2 (6)N1—C13—C14—O3175.6 (4)
C5—C6—C7—N2178.5 (4)C12—C13—C14—O36.6 (6)
O2—C2—C7—C6179.2 (3)N1—C13—C14—N34.9 (5)
C3—C2—C7—C60.6 (5)C12—C13—C14—N3172.9 (4)
O2—C2—C7—N20.7 (5)C14—N3—C15—C1620.5 (6)
C3—C2—C7—N2179.1 (3)C14—N3—C15—C20160.5 (4)
C8—N2—C7—C65.1 (6)C20—C15—C16—C170.9 (6)
C8—N2—C7—C2176.6 (3)N3—C15—C16—C17179.9 (4)
C7—N2—C8—O12.0 (7)C15—C16—C17—C180.5 (6)
C7—N2—C8—C9176.5 (3)C16—C17—C18—C190.4 (6)
C13—N1—C9—C101.6 (5)C17—C18—C19—C200.6 (6)
C13—N1—C9—C8177.5 (4)C21—O4—C20—C198.4 (5)
O1—C8—C9—N1176.1 (4)C21—O4—C20—C15171.2 (4)
N2—C8—C9—N15.4 (5)C18—C19—C20—O4179.4 (4)
O1—C8—C9—C104.8 (6)C18—C19—C20—C151.0 (6)
N2—C8—C9—C10173.8 (3)C16—C15—C20—O4179.2 (3)
N1—C9—C10—C112.1 (6)N3—C15—C20—O40.1 (5)
C8—C9—C10—C11177.0 (4)C16—C15—C20—C191.2 (6)
C9—C10—C11—C121.5 (6)N3—C15—C20—C19179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.862.192.602 (4)110
N2—H2A···N10.862.262.700 (4)112
N3—H3A···O40.862.222.580 (4)105
N3—H3A···N10.862.252.678 (4)111
C6—H6A···O10.932.282.891 (5)123
C11—H11A···O3i0.932.573.260 (4)132
C16—H16A···O30.932.372.917 (4)118
C21—H21B···O1ii0.962.493.124 (5)124
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y1/2, z+1/2.
 

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