In the title tridentate ligand, C
21H
19N
3O
4, 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
CCDC reference: 177202
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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.
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
C21H19N3O4 | Dx = 1.314 Mg m−3 |
Mr = 377.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4522 reflections |
a = 4.7919 (9) Å | θ = 1–27.5° |
b = 15.775 (3) Å | µ = 0.09 mm−1 |
c = 25.228 (5) Å | T = 294 K |
V = 1907.1 (6) Å3 | Plate, colourless |
Z = 4 | 0.24 × 0.20 × 0.18 mm |
F(000) = 792 | |
Data collection top
Siemens CCD area-detector diffractometer | 2571 independent reflections |
Radiation source: fine-focus sealed tube | 1007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
Detector resolution: 8.3 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans | h = −6→5 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −20→19 |
Tmin = 0.978, Tmax = 0.984 | l = −29→32 |
12538 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-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 reflections | Δρmax = 0.14 e Å−3 |
253 parameters | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.3689 (8) | 0.20900 (18) | 0.25572 (11) | 0.1129 (13) | |
O2 | 1.0181 (7) | −0.02251 (16) | 0.23433 (10) | 0.0797 (8) | |
O3 | 1.1365 (7) | 0.10741 (15) | 0.48373 (10) | 0.0982 (11) | |
O4 | 1.0396 (6) | −0.11966 (15) | 0.36016 (9) | 0.0738 (8) | |
N1 | 0.7888 (6) | 0.13141 (16) | 0.36080 (11) | 0.0543 (8) | |
N2 | 0.6785 (7) | 0.10072 (17) | 0.25762 (10) | 0.0636 (9) | |
H2A | 0.7890 | 0.0741 | 0.2787 | 0.076* | |
N3 | 1.1108 (7) | 0.01954 (17) | 0.41213 (10) | 0.0630 (9) | |
H3A | 1.0491 | 0.0171 | 0.3801 | 0.076* | |
C1 | 1.2034 (10) | −0.0912 (2) | 0.22548 (16) | 0.0900 (15) | |
H1B | 1.3066 | −0.1025 | 0.2573 | 0.135* | |
H1C | 1.3304 | −0.0769 | 0.1974 | 0.135* | |
H1D | 1.0985 | −0.1406 | 0.2157 | 0.135* | |
C2 | 0.8516 (9) | 0.0033 (3) | 0.19318 (16) | 0.0662 (11) | |
C3 | 0.8550 (10) | −0.0318 (2) | 0.14311 (18) | 0.0794 (14) | |
H3B | 0.9765 | −0.0758 | 0.1350 | 0.095* | |
C4 | 0.6727 (12) | 0.0001 (3) | 0.10503 (18) | 0.0898 (17) | |
H4A | 0.6746 | −0.0231 | 0.0711 | 0.108* | |
C5 | 0.4911 (11) | 0.0645 (3) | 0.11623 (16) | 0.0862 (15) | |
H5A | 0.3690 | 0.0846 | 0.0905 | 0.103* | |
C6 | 0.4926 (10) | 0.0994 (2) | 0.16694 (15) | 0.0725 (12) | |
H6A | 0.3711 | 0.1435 | 0.1750 | 0.087* | |
C7 | 0.6699 (9) | 0.0697 (2) | 0.20503 (14) | 0.0591 (11) | |
C8 | 0.5389 (10) | 0.1658 (2) | 0.27928 (15) | 0.0675 (12) | |
C9 | 0.6133 (9) | 0.1839 (2) | 0.33589 (14) | 0.0582 (11) | |
C10 | 0.5008 (9) | 0.2547 (2) | 0.35993 (15) | 0.0725 (12) | |
H10A | 0.3745 | 0.2890 | 0.3419 | 0.087* | |
C11 | 0.5789 (10) | 0.2738 (2) | 0.41112 (15) | 0.0801 (13) | |
H11A | 0.5092 | 0.3219 | 0.4278 | 0.096* | |
C12 | 0.7589 (10) | 0.2216 (2) | 0.43699 (14) | 0.0742 (13) | |
H12A | 0.8129 | 0.2331 | 0.4717 | 0.089* | |
C13 | 0.8609 (9) | 0.1505 (2) | 0.41071 (14) | 0.0589 (11) | |
C14 | 1.0511 (9) | 0.0906 (2) | 0.43950 (15) | 0.0642 (11) | |
C15 | 1.2627 (8) | −0.0510 (2) | 0.43016 (13) | 0.0539 (10) | |
C16 | 1.4442 (9) | −0.0510 (2) | 0.47177 (14) | 0.0701 (12) | |
H16A | 1.4746 | −0.0013 | 0.4907 | 0.084* | |
C17 | 1.5841 (9) | −0.1246 (3) | 0.48614 (15) | 0.0755 (12) | |
H17A | 1.7064 | −0.1243 | 0.5148 | 0.091* | |
C18 | 1.5413 (9) | −0.1976 (2) | 0.45809 (15) | 0.0731 (12) | |
H18A | 1.6358 | −0.2468 | 0.4676 | 0.088* | |
C19 | 1.3606 (9) | −0.1988 (2) | 0.41614 (14) | 0.0665 (11) | |
H19A | 1.3315 | −0.2488 | 0.3975 | 0.080* | |
C20 | 1.2214 (8) | −0.1260 (2) | 0.40137 (13) | 0.0565 (10) | |
C21 | 0.9571 (11) | −0.1966 (2) | 0.33382 (14) | 0.0881 (15) | |
H21B | 0.8291 | −0.1834 | 0.3057 | 0.132* | |
H21C | 0.8680 | −0.2337 | 0.3588 | 0.132* | |
H21A | 1.1189 | −0.2240 | 0.3194 | 0.132* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.161 (3) | 0.093 (2) | 0.084 (2) | 0.064 (3) | −0.041 (2) | −0.0022 (17) |
O2 | 0.082 (2) | 0.0748 (18) | 0.082 (2) | 0.0167 (19) | 0.0105 (18) | −0.0082 (15) |
O3 | 0.155 (3) | 0.0761 (17) | 0.0634 (17) | 0.027 (2) | −0.036 (2) | −0.0266 (15) |
O4 | 0.093 (2) | 0.0621 (15) | 0.0660 (16) | 0.0006 (17) | −0.0252 (16) | −0.0161 (13) |
N1 | 0.069 (2) | 0.0438 (16) | 0.0495 (18) | 0.0060 (18) | 0.0004 (16) | −0.0019 (15) |
N2 | 0.087 (3) | 0.0550 (18) | 0.0489 (19) | 0.013 (2) | −0.0097 (18) | −0.0037 (16) |
N3 | 0.087 (3) | 0.0553 (18) | 0.0465 (18) | 0.005 (2) | −0.0158 (17) | −0.0090 (15) |
C1 | 0.080 (3) | 0.064 (3) | 0.126 (4) | 0.014 (3) | 0.025 (3) | −0.001 (2) |
C2 | 0.072 (3) | 0.064 (3) | 0.063 (3) | −0.012 (3) | 0.008 (3) | 0.003 (2) |
C3 | 0.101 (4) | 0.069 (3) | 0.068 (3) | −0.026 (3) | 0.034 (3) | −0.013 (3) |
C4 | 0.129 (5) | 0.085 (3) | 0.055 (3) | −0.049 (4) | 0.017 (3) | −0.002 (3) |
C5 | 0.118 (4) | 0.084 (3) | 0.057 (3) | −0.035 (4) | −0.005 (3) | 0.008 (2) |
C6 | 0.094 (4) | 0.060 (2) | 0.063 (3) | −0.010 (3) | −0.013 (3) | 0.011 (2) |
C7 | 0.076 (3) | 0.052 (2) | 0.049 (2) | −0.006 (2) | 0.002 (2) | −0.0013 (19) |
C8 | 0.090 (4) | 0.047 (2) | 0.065 (3) | 0.012 (3) | −0.001 (3) | −0.001 (2) |
C9 | 0.076 (3) | 0.044 (2) | 0.055 (2) | 0.001 (2) | 0.004 (2) | 0.0013 (19) |
C10 | 0.093 (4) | 0.053 (2) | 0.072 (3) | 0.021 (3) | 0.007 (3) | 0.004 (2) |
C11 | 0.116 (4) | 0.058 (2) | 0.066 (3) | 0.019 (3) | 0.008 (3) | −0.012 (2) |
C12 | 0.111 (4) | 0.052 (2) | 0.060 (3) | 0.004 (3) | 0.004 (3) | −0.007 (2) |
C13 | 0.081 (3) | 0.044 (2) | 0.052 (2) | −0.002 (2) | 0.001 (2) | −0.0060 (19) |
C14 | 0.084 (3) | 0.057 (2) | 0.051 (2) | 0.005 (3) | −0.006 (2) | −0.009 (2) |
C15 | 0.062 (3) | 0.053 (2) | 0.048 (2) | 0.002 (2) | −0.008 (2) | −0.0011 (19) |
C16 | 0.082 (3) | 0.067 (2) | 0.061 (2) | 0.001 (3) | −0.020 (2) | −0.009 (2) |
C17 | 0.075 (3) | 0.085 (3) | 0.067 (3) | 0.006 (3) | −0.018 (2) | 0.007 (2) |
C18 | 0.083 (3) | 0.067 (3) | 0.069 (3) | 0.012 (3) | −0.005 (3) | 0.003 (2) |
C19 | 0.073 (3) | 0.060 (3) | 0.067 (3) | −0.003 (3) | 0.000 (2) | −0.001 (2) |
C20 | 0.064 (3) | 0.057 (2) | 0.048 (2) | −0.002 (2) | −0.005 (2) | −0.002 (2) |
C21 | 0.100 (4) | 0.081 (3) | 0.083 (3) | −0.028 (3) | −0.011 (3) | −0.029 (2) |
Geometric parameters (Å, º) top
O1—C8 | 1.217 (4) | C4—C5 | 1.368 (6) |
O2—C2 | 1.371 (4) | C5—C6 | 1.393 (5) |
O2—C1 | 1.418 (4) | C6—C7 | 1.366 (5) |
O3—C14 | 1.218 (4) | C8—C9 | 1.499 (5) |
O4—C20 | 1.360 (4) | C9—C10 | 1.381 (4) |
O4—C21 | 1.439 (4) | C10—C11 | 1.378 (5) |
N1—C9 | 1.337 (4) | C11—C12 | 1.360 (5) |
N1—C13 | 1.340 (4) | C12—C13 | 1.391 (4) |
N2—C8 | 1.342 (4) | C13—C14 | 1.500 (5) |
N2—C7 | 1.415 (4) | C15—C16 | 1.363 (4) |
N3—C14 | 1.348 (4) | C15—C20 | 1.402 (4) |
N3—C15 | 1.405 (4) | C16—C17 | 1.390 (5) |
C2—C3 | 1.379 (5) | C17—C18 | 1.367 (4) |
C2—C7 | 1.394 (5) | C18—C19 | 1.368 (5) |
C3—C4 | 1.392 (5) | C19—C20 | 1.380 (5) |
| | | |
C2—O2—C1 | 118.2 (3) | C10—C9—C8 | 118.7 (4) |
C20—O4—C21 | 117.9 (3) | C11—C10—C9 | 118.8 (4) |
C9—N1—C13 | 117.7 (3) | C12—C11—C10 | 119.4 (4) |
C8—N2—C7 | 129.2 (3) | C11—C12—C13 | 118.8 (4) |
C14—N3—C15 | 127.1 (3) | N1—C13—C12 | 122.6 (4) |
O2—C2—C3 | 124.5 (4) | N1—C13—C14 | 118.0 (3) |
O2—C2—C7 | 115.1 (4) | C12—C13—C14 | 119.3 (3) |
C3—C2—C7 | 120.3 (4) | O3—C14—N3 | 125.4 (4) |
C2—C3—C4 | 118.7 (4) | O3—C14—C13 | 120.7 (3) |
C5—C4—C3 | 121.7 (4) | N3—C14—C13 | 113.9 (3) |
C4—C5—C6 | 118.7 (5) | C16—C15—C20 | 119.3 (4) |
C7—C6—C5 | 120.9 (4) | C16—C15—N3 | 125.5 (3) |
C6—C7—C2 | 119.7 (4) | C20—C15—N3 | 115.3 (3) |
C6—C7—N2 | 124.0 (4) | C15—C16—C17 | 120.6 (4) |
C2—C7—N2 | 116.3 (4) | C18—C17—C16 | 119.8 (4) |
O1—C8—N2 | 124.3 (4) | C17—C18—C19 | 120.4 (4) |
O1—C8—C9 | 121.1 (4) | C18—C19—C20 | 120.3 (4) |
N2—C8—C9 | 114.6 (4) | O4—C20—C19 | 125.2 (3) |
N1—C9—C10 | 122.7 (3) | O4—C20—C15 | 115.1 (3) |
N1—C9—C8 | 118.6 (3) | C19—C20—C15 | 119.6 (4) |
| | | |
C1—O2—C2—C3 | −1.3 (5) | C10—C11—C12—C13 | 0.5 (6) |
C1—O2—C2—C7 | 178.5 (3) | C9—N1—C13—C12 | 0.5 (5) |
O2—C2—C3—C4 | 179.4 (3) | C9—N1—C13—C14 | 178.3 (3) |
C7—C2—C3—C4 | −0.3 (5) | C11—C12—C13—N1 | 0.0 (6) |
C2—C3—C4—C5 | −0.4 (6) | C11—C12—C13—C14 | −177.7 (4) |
C3—C4—C5—C6 | 0.8 (6) | C15—N3—C14—O3 | 5.1 (7) |
C4—C5—C6—C7 | −0.5 (6) | C15—N3—C14—C13 | −174.3 (3) |
C5—C6—C7—C2 | −0.2 (6) | N1—C13—C14—O3 | 175.6 (4) |
C5—C6—C7—N2 | −178.5 (4) | C12—C13—C14—O3 | −6.6 (6) |
O2—C2—C7—C6 | −179.2 (3) | N1—C13—C14—N3 | −4.9 (5) |
C3—C2—C7—C6 | 0.6 (5) | C12—C13—C14—N3 | 172.9 (4) |
O2—C2—C7—N2 | −0.7 (5) | C14—N3—C15—C16 | −20.5 (6) |
C3—C2—C7—N2 | 179.1 (3) | C14—N3—C15—C20 | 160.5 (4) |
C8—N2—C7—C6 | −5.1 (6) | C20—C15—C16—C17 | −0.9 (6) |
C8—N2—C7—C2 | 176.6 (3) | N3—C15—C16—C17 | −179.9 (4) |
C7—N2—C8—O1 | 2.0 (7) | C15—C16—C17—C18 | 0.5 (6) |
C7—N2—C8—C9 | −176.5 (3) | C16—C17—C18—C19 | −0.4 (6) |
C13—N1—C9—C10 | −1.6 (5) | C17—C18—C19—C20 | 0.6 (6) |
C13—N1—C9—C8 | 177.5 (4) | C21—O4—C20—C19 | 8.4 (5) |
O1—C8—C9—N1 | 176.1 (4) | C21—O4—C20—C15 | −171.2 (4) |
N2—C8—C9—N1 | −5.4 (5) | C18—C19—C20—O4 | 179.4 (4) |
O1—C8—C9—C10 | −4.8 (6) | C18—C19—C20—C15 | −1.0 (6) |
N2—C8—C9—C10 | 173.8 (3) | C16—C15—C20—O4 | −179.2 (3) |
N1—C9—C10—C11 | 2.1 (6) | N3—C15—C20—O4 | −0.1 (5) |
C8—C9—C10—C11 | −177.0 (4) | C16—C15—C20—C19 | 1.2 (6) |
C9—C10—C11—C12 | −1.5 (6) | N3—C15—C20—C19 | −179.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.19 | 2.602 (4) | 110 |
N2—H2A···N1 | 0.86 | 2.26 | 2.700 (4) | 112 |
N3—H3A···O4 | 0.86 | 2.22 | 2.580 (4) | 105 |
N3—H3A···N1 | 0.86 | 2.25 | 2.678 (4) | 111 |
C6—H6A···O1 | 0.93 | 2.28 | 2.891 (5) | 123 |
C11—H11A···O3i | 0.93 | 2.57 | 3.260 (4) | 132 |
C16—H16A···O3 | 0.93 | 2.37 | 2.917 (4) | 118 |
C21—H21B···O1ii | 0.96 | 2.49 | 3.124 (5) | 124 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1/2. |