organic compounds
N,N′-Diethyl-N,N′-diphenylpyridine-2,6-dicarboxamide
aInstitute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo sq. 2, 166 10 Prague 6, Czech Republic, bFaculty of Environmental Sciences, Czech University of Life Sciences, Prague, Kamýcká 129, 165 21 Prague 6, Czech Republic, and cKhlopin Radium Institute, Research and Production Association, 2nd Murinskiy Prospect b. 28, 194021 St Petersburg, Russian Federation
*Correspondence e-mail: klepetab@centrum.cz
The 23H23N3O2, contains two molecules in both of which, one amide N atom is in a syn position with respect to the pyridine N atom, while the other amide N atom is in an anti position (the syn--anti conformation). There are minor conformational differences between the two molecules, as reflected in the Npyridine—C—C—Namide torsion angles of −44.9 (3) and 136.0 (2)° for one molecule and 43.5 (3) and −131.1 (2)° for the other molecule. However, the two molecules show significant differences in the orientation of an ethyl group, with corresponding C—C—N—C torsion angles of 86.6 (3)° for one molecule and 79.6 (3)° for the other molecule. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular network.
of the title compound, CRelated literature
For the extractive properties of some pyridine-dicarboxamides, see: Alyapyshev et al. (2004); Du Preez et al. (1987). For synthetic details, see: Shimada et al. (2004); Nikitskaya et al. (1958). For related structures, see: Malone et al. (1997); Fujiwara et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: CRYSTALS, PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812009026/pv2514sup1.cif
contains datablocks global, I. DOI:Supporting information file. DOI: 10.1107/S1600536812009026/pv2514Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812009026/pv2514Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812009026/pv2514Isup4.cml
The title compound was synthesized as described in Shimada et al., (2004), and Nikitskaya et al., (1958). Colourless crystals were prepared by slow evaporation from acetonitrile.
The hydrogen atoms were located in in the Δρ map, but were repositioned geometrically. They were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (Cmethyl—H = 0.96, Cmethylene—H = 0.97, Caryl—H = 0.93 Å) and fixed at those positions in the final cycles of refinements. The Uiso(H) were allowed in the range 1.2–1.5 times Ueq of the parent atom.
Pyridine-dicarboxamides have been studied recently for significant extractive properties (Alyapyshev et al., 2004). The factors which lead to stabilization of low symmetry five-coordinate complexes, when using neutral donor ligands, have been reported (Du Preez et al., 1987).
The title compound crystallizes with two independent molecules (1 and 2) (Figs. 1 & 2) in an
The molecules consist of a pyridine ring between two amide groups in the ortho positions of this ring and ethyl and phenyl groups on the amide nitrogen. Both molecules in the adopt a syn-anti conformation, in contrast to the syn-syn conformation found in N,N'-diphenylpyridine-2,6-dicarboxamide (Malone et al., 1997), but analogous to that observed in N,N'-dimethyl-N,N'-diphenylpyridine-2,6-dicarboxamide (Fujiwara et al., 2008).There are minor conformational differences in the two molecules as reflected in the torsion angles Npyridine—C—C—Namide being -44.9 (3) and 136.0 (2)° for molecule 1 and 43.5 (3) and -131.1 (2)° for molecule 2 and the torsion angles Npyridine—C—C—Oamide being 134.1 (3) and -46.8 (3)° for molecule 1 and -132.6 (3) and 51.2 (3)° for molecule 2. However, the two molecules show significant differences in the orientation of an ethyl group (the corresponding torsion angles are C17—C16—N3—C15 86.6 (3)° for molecule 1 and C40—C39—N6—C38 79.6 (3)° for molecule 2).
The molecules are connected via weak intermolecular C—H···O interactions between the amide oxygen atoms and ethyl and phenyl groups, forming a three-dimensional network (Fig. 3).
For the extractive properties of some pyridine-dicarboxamides, see: Alyapyshev et al. (2004); Du Preez et al. (1987). For synthetic details, see: Shimada et al. (2004); Nikitskaya et al. (1958). For related structures, see: Malone et al. (1997); Fujiwara et al. (2008).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. Molecule 1 of the title compound viewed perpendicular to the pyridine ring plane. Displacement ellipsoids are drawn at the 50% probability level, H atoms are shown as spheres of arbitrary radius. | |
Fig. 2. Molecule 2 of the title compound viewed perpendicular to the pyridine ring plane. Displacement ellipsoids are drawn at the 50% probability level, H atoms are shown as spheres of arbitrary radius. | |
Fig. 3. Projection along the a axis with highlighted hydrogen bonds between the molecules (H atoms not involved in hydrogen bonds were omitted for clarity). |
C23H23N3O2 | Z = 4 |
Mr = 373.45 | F(000) = 792 |
Triclinic, P1 | Dx = 1.225 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 12.1879 (17) Å | Cell parameters from 6449 reflections |
b = 12.2371 (15) Å | θ = 4.6–85.1° |
c = 13.6798 (17) Å | µ = 0.63 mm−1 |
α = 83.971 (10)° | T = 170 K |
β = 86.919 (11)° | Prism, colourless |
γ = 87.744 (10)° | 0.37 × 0.19 × 0.15 mm |
V = 2024.9 (5) Å3 |
Oxford Diffraction Xcalibur diffractometer | 4586 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.111 |
φ & ω scans | θmax = 85.7°, θmin = 4.6° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −15→14 |
Tmin = 0.496, Tmax = 1.000 | k = −15→15 |
51216 measured reflections | l = −17→17 |
8553 independent reflections |
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.062 | Method, part 1, Chebychev polynomial, [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 15.1 3.75 12.4 3.85 |
S = 1.14 | (Δ/σ)max = 0.003 |
4586 reflections | Δρmax = 0.24 e Å−3 |
505 parameters | Δρmin = −0.25 e Å−3 |
0 restraints |
C23H23N3O2 | γ = 87.744 (10)° |
Mr = 373.45 | V = 2024.9 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.1879 (17) Å | Cu Kα radiation |
b = 12.2371 (15) Å | µ = 0.63 mm−1 |
c = 13.6798 (17) Å | T = 170 K |
α = 83.971 (10)° | 0.37 × 0.19 × 0.15 mm |
β = 86.919 (11)° |
Oxford Diffraction Xcalibur diffractometer | 8553 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 4586 reflections with I > 2σ(I) |
Tmin = 0.496, Tmax = 1.000 | Rint = 0.111 |
51216 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.24 e Å−3 |
4586 reflections | Δρmin = −0.25 e Å−3 |
505 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4330 (2) | 0.2215 (2) | 0.95742 (19) | 0.0386 | |
C2 | 0.4133 (2) | 0.1145 (2) | 0.9394 (2) | 0.0470 | |
C3 | 0.3268 (2) | 0.0603 (2) | 0.9907 (2) | 0.0466 | |
C4 | 0.2643 (2) | 0.1148 (2) | 1.0583 (2) | 0.0419 | |
C5 | 0.2913 (2) | 0.21987 (19) | 1.07487 (18) | 0.0360 | |
C6 | 0.5312 (2) | 0.2762 (2) | 0.9039 (2) | 0.0419 | |
C7 | 0.6225 (2) | 0.4370 (2) | 0.8246 (2) | 0.0498 | |
C8 | 0.6299 (3) | 0.4396 (3) | 0.7145 (2) | 0.0742 | |
C9 | 0.4200 (2) | 0.4453 (2) | 0.86369 (18) | 0.0389 | |
C10 | 0.4104 (2) | 0.5463 (2) | 0.9016 (2) | 0.0498 | |
C11 | 0.3109 (3) | 0.6049 (2) | 0.8987 (2) | 0.0580 | |
C12 | 0.2219 (3) | 0.5641 (3) | 0.8578 (2) | 0.0575 | |
C13 | 0.2333 (2) | 0.4658 (2) | 0.8175 (2) | 0.0526 | |
C14 | 0.3322 (2) | 0.4063 (2) | 0.81921 (19) | 0.0425 | |
C15 | 0.2394 (2) | 0.2773 (2) | 1.15845 (19) | 0.0375 | |
C16 | 0.0788 (2) | 0.3366 (3) | 1.2565 (2) | 0.0514 | |
C17 | 0.0639 (3) | 0.4588 (3) | 1.2328 (3) | 0.0633 | |
C18 | 0.0545 (2) | 0.2535 (2) | 1.10042 (19) | 0.0418 | |
C19 | 0.0553 (2) | 0.3071 (2) | 1.0066 (2) | 0.0507 | |
C20 | −0.0191 (3) | 0.2776 (3) | 0.9415 (2) | 0.0609 | |
C21 | −0.0940 (3) | 0.1977 (3) | 0.9701 (2) | 0.0662 | |
C22 | −0.0940 (3) | 0.1460 (3) | 1.0641 (3) | 0.0677 | |
C23 | −0.0199 (2) | 0.1736 (3) | 1.1292 (2) | 0.0544 | |
O1 | 0.61698 (16) | 0.22033 (17) | 0.89549 (17) | 0.0626 | |
O2 | 0.29906 (15) | 0.31442 (15) | 1.21633 (13) | 0.0468 | |
N3 | 0.12827 (17) | 0.28338 (18) | 1.17164 (15) | 0.0424 | |
N1 | 0.37461 (16) | 0.27412 (16) | 1.02507 (15) | 0.0357 | |
N2 | 0.52272 (17) | 0.38349 (17) | 0.86884 (16) | 0.0418 | |
C24 | 0.0880 (2) | 0.7024 (2) | 0.49936 (19) | 0.0397 | |
C25 | 0.1251 (2) | 0.5935 (2) | 0.4997 (2) | 0.0451 | |
C26 | 0.2181 (2) | 0.5602 (2) | 0.5492 (2) | 0.0496 | |
C27 | 0.2706 (2) | 0.6350 (2) | 0.5969 (2) | 0.0444 | |
C28 | 0.2275 (2) | 0.7416 (2) | 0.59462 (18) | 0.0380 | |
C29 | −0.0175 (2) | 0.7392 (2) | 0.4509 (2) | 0.0436 | |
C30 | −0.1313 (2) | 0.8812 (2) | 0.3630 (2) | 0.0513 | |
C31 | −0.1468 (3) | 0.8498 (3) | 0.2607 (3) | 0.0708 | |
C32 | 0.0714 (2) | 0.9001 (2) | 0.36448 (19) | 0.0387 | |
C33 | 0.1532 (2) | 0.8537 (2) | 0.30747 (19) | 0.0442 | |
C34 | 0.2459 (2) | 0.9125 (3) | 0.2747 (2) | 0.0564 | |
C35 | 0.2549 (3) | 1.0171 (3) | 0.2993 (2) | 0.0597 | |
C36 | 0.1719 (3) | 1.0653 (2) | 0.3539 (2) | 0.0550 | |
C37 | 0.0792 (2) | 1.0082 (2) | 0.3859 (2) | 0.0463 | |
C38 | 0.2727 (2) | 0.8246 (2) | 0.65339 (18) | 0.0401 | |
C39 | 0.4275 (2) | 0.9181 (2) | 0.7089 (2) | 0.0497 | |
C40 | 0.4483 (3) | 0.8608 (3) | 0.8096 (2) | 0.0637 | |
C41 | 0.4545 (2) | 0.8057 (2) | 0.5676 (2) | 0.0425 | |
C42 | 0.5530 (2) | 0.7520 (2) | 0.5924 (2) | 0.0500 | |
C43 | 0.6267 (3) | 0.7185 (3) | 0.5201 (2) | 0.0598 | |
C44 | 0.6015 (3) | 0.7378 (3) | 0.4228 (2) | 0.0631 | |
C45 | 0.5031 (3) | 0.7917 (3) | 0.3978 (2) | 0.0583 | |
C46 | 0.4301 (2) | 0.8273 (2) | 0.4697 (2) | 0.0489 | |
O3 | −0.09683 (16) | 0.67804 (17) | 0.46445 (18) | 0.0632 | |
O4 | 0.21148 (15) | 0.87033 (16) | 0.71207 (14) | 0.0519 | |
N4 | 0.13673 (16) | 0.77617 (16) | 0.54716 (16) | 0.0382 | |
N5 | −0.02370 (16) | 0.83951 (17) | 0.39990 (16) | 0.0415 | |
N6 | 0.38214 (17) | 0.84479 (18) | 0.64277 (16) | 0.0423 | |
H231 | −0.0210 | 0.1386 | 1.1936 | 0.0654* | |
H221 | −0.1462 | 0.0916 | 1.0845 | 0.0811* | |
H211 | −0.1445 | 0.1790 | 0.9260 | 0.0788* | |
H201 | −0.0173 | 0.3119 | 0.8768 | 0.0734* | |
H191 | 0.1060 | 0.3630 | 0.9869 | 0.0616* | |
H161 | 0.1259 | 0.3218 | 1.3129 | 0.0612* | |
H162 | 0.0068 | 0.3057 | 1.2741 | 0.0615* | |
H173 | 0.0244 | 0.4913 | 1.2878 | 0.0944* | |
H172 | 0.1344 | 0.4930 | 1.2207 | 0.0951* | |
H171 | 0.0213 | 0.4736 | 1.1745 | 0.0948* | |
H141 | 0.3408 | 0.3384 | 0.7909 | 0.0512* | |
H131 | 0.1734 | 0.4373 | 0.7870 | 0.0622* | |
H121 | 0.1543 | 0.6034 | 0.8558 | 0.0680* | |
H111 | 0.3023 | 0.6723 | 0.9263 | 0.0698* | |
H101 | 0.4709 | 0.5746 | 0.9310 | 0.0594* | |
H71 | 0.6189 | 0.5137 | 0.8412 | 0.0594* | |
H72 | 0.6863 | 0.3958 | 0.8527 | 0.0604* | |
H83 | 0.6934 | 0.4796 | 0.6865 | 0.1108* | |
H82 | 0.5637 | 0.4769 | 0.6886 | 0.1109* | |
H81 | 0.6339 | 0.3658 | 0.6952 | 0.1106* | |
H21 | 0.4576 | 0.0801 | 0.8922 | 0.0559* | |
H31 | 0.3093 | −0.0123 | 0.9805 | 0.0562* | |
H41 | 0.2054 | 0.0799 | 1.0950 | 0.0511* | |
H421 | 0.5689 | 0.7381 | 0.6588 | 0.0599* | |
H431 | 0.6959 | 0.6849 | 0.5362 | 0.0718* | |
H441 | 0.6513 | 0.7140 | 0.3732 | 0.0760* | |
H451 | 0.4856 | 0.8042 | 0.3310 | 0.0698* | |
H461 | 0.3646 | 0.8654 | 0.4525 | 0.0592* | |
H391 | 0.3780 | 0.9818 | 0.7126 | 0.0601* | |
H392 | 0.4953 | 0.9472 | 0.6771 | 0.0601* | |
H403 | 0.4874 | 0.9106 | 0.8475 | 0.0956* | |
H402 | 0.3775 | 0.8418 | 0.8441 | 0.0962* | |
H401 | 0.4928 | 0.7931 | 0.8025 | 0.0955* | |
H251 | 0.0875 | 0.5434 | 0.4674 | 0.0537* | |
H261 | 0.2456 | 0.4864 | 0.5501 | 0.0607* | |
H271 | 0.3332 | 0.6137 | 0.6301 | 0.0538* | |
H331 | 0.1465 | 0.7825 | 0.2921 | 0.0536* | |
H341 | 0.3009 | 0.8793 | 0.2351 | 0.0679* | |
H351 | 0.3176 | 1.0570 | 0.2771 | 0.0718* | |
H361 | 0.1779 | 1.1372 | 0.3689 | 0.0659* | |
H371 | 0.0216 | 1.0420 | 0.4232 | 0.0553* | |
H301 | −0.1352 | 0.9625 | 0.3612 | 0.0615* | |
H302 | −0.1898 | 0.8524 | 0.4087 | 0.0618* | |
H311 | −0.2184 | 0.8768 | 0.2392 | 0.1055* | |
H313 | −0.0901 | 0.8829 | 0.2156 | 0.1060* | |
H312 | −0.1410 | 0.7692 | 0.2607 | 0.1061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0370 (13) | 0.0365 (13) | 0.0422 (14) | −0.0022 (11) | −0.0021 (11) | −0.0034 (11) |
C2 | 0.0490 (16) | 0.0411 (15) | 0.0518 (16) | −0.0016 (12) | 0.0018 (13) | −0.0109 (12) |
C3 | 0.0500 (16) | 0.0362 (14) | 0.0552 (17) | −0.0078 (12) | −0.0048 (14) | −0.0080 (12) |
C4 | 0.0372 (14) | 0.0418 (14) | 0.0463 (15) | −0.0073 (11) | −0.0030 (12) | −0.0002 (12) |
C5 | 0.0339 (13) | 0.0349 (13) | 0.0384 (13) | −0.0022 (10) | −0.0046 (11) | 0.0014 (11) |
C6 | 0.0373 (14) | 0.0418 (15) | 0.0480 (15) | −0.0032 (12) | 0.0014 (12) | −0.0120 (12) |
C7 | 0.0425 (15) | 0.0523 (16) | 0.0553 (17) | −0.0139 (13) | 0.0059 (13) | −0.0093 (13) |
C8 | 0.071 (2) | 0.090 (3) | 0.062 (2) | −0.031 (2) | 0.0159 (18) | −0.0085 (18) |
C9 | 0.0411 (14) | 0.0384 (14) | 0.0365 (13) | −0.0055 (11) | 0.0037 (11) | −0.0027 (11) |
C10 | 0.0523 (17) | 0.0406 (15) | 0.0574 (17) | −0.0071 (13) | −0.0044 (14) | −0.0057 (13) |
C11 | 0.068 (2) | 0.0381 (15) | 0.067 (2) | 0.0043 (14) | −0.0023 (16) | −0.0062 (14) |
C12 | 0.0490 (17) | 0.0528 (18) | 0.067 (2) | 0.0027 (14) | −0.0016 (15) | 0.0064 (15) |
C13 | 0.0479 (17) | 0.0573 (18) | 0.0521 (17) | −0.0078 (14) | −0.0087 (14) | 0.0013 (14) |
C14 | 0.0462 (15) | 0.0427 (14) | 0.0388 (14) | −0.0084 (12) | −0.0022 (12) | −0.0036 (11) |
C15 | 0.0372 (14) | 0.0351 (13) | 0.0397 (14) | −0.0040 (11) | −0.0031 (12) | 0.0002 (11) |
C16 | 0.0459 (16) | 0.0668 (19) | 0.0413 (15) | −0.0031 (14) | 0.0078 (13) | −0.0092 (14) |
C17 | 0.0520 (18) | 0.066 (2) | 0.075 (2) | 0.0078 (16) | −0.0089 (16) | −0.0252 (17) |
C18 | 0.0321 (13) | 0.0548 (16) | 0.0390 (14) | −0.0035 (12) | −0.0009 (11) | −0.0063 (12) |
C19 | 0.0468 (16) | 0.0563 (17) | 0.0468 (16) | −0.0020 (13) | −0.0008 (13) | 0.0041 (13) |
C20 | 0.0582 (19) | 0.079 (2) | 0.0453 (17) | 0.0049 (17) | −0.0091 (15) | −0.0032 (15) |
C21 | 0.0454 (17) | 0.099 (3) | 0.058 (2) | −0.0085 (18) | −0.0122 (15) | −0.0158 (19) |
C22 | 0.0478 (18) | 0.095 (3) | 0.062 (2) | −0.0235 (18) | −0.0053 (16) | −0.0051 (18) |
C23 | 0.0424 (15) | 0.075 (2) | 0.0447 (16) | −0.0145 (15) | −0.0021 (13) | 0.0042 (14) |
O1 | 0.0434 (11) | 0.0531 (12) | 0.0899 (16) | 0.0060 (10) | 0.0121 (11) | −0.0106 (11) |
O2 | 0.0454 (11) | 0.0521 (11) | 0.0443 (10) | −0.0057 (9) | −0.0053 (9) | −0.0085 (9) |
N3 | 0.0366 (12) | 0.0524 (13) | 0.0379 (12) | −0.0026 (10) | 0.0004 (9) | −0.0042 (10) |
N1 | 0.0316 (11) | 0.0365 (11) | 0.0387 (11) | −0.0043 (9) | −0.0029 (9) | −0.0009 (9) |
N2 | 0.0364 (12) | 0.0399 (12) | 0.0492 (13) | −0.0060 (9) | 0.0038 (10) | −0.0059 (10) |
C24 | 0.0377 (14) | 0.0335 (13) | 0.0462 (15) | −0.0051 (11) | 0.0063 (12) | 0.0016 (11) |
C25 | 0.0454 (15) | 0.0366 (14) | 0.0525 (16) | −0.0032 (12) | 0.0006 (13) | −0.0021 (12) |
C26 | 0.0493 (17) | 0.0334 (14) | 0.0635 (18) | 0.0034 (12) | 0.0046 (14) | 0.0016 (13) |
C27 | 0.0401 (14) | 0.0397 (14) | 0.0512 (16) | 0.0030 (12) | −0.0020 (12) | 0.0038 (12) |
C28 | 0.0304 (13) | 0.0411 (14) | 0.0400 (14) | 0.0019 (11) | 0.0050 (11) | 0.0027 (11) |
C29 | 0.0354 (14) | 0.0361 (14) | 0.0598 (17) | −0.0027 (11) | −0.0029 (13) | −0.0066 (12) |
C30 | 0.0409 (15) | 0.0528 (17) | 0.0599 (18) | 0.0059 (13) | −0.0098 (14) | −0.0035 (14) |
C31 | 0.057 (2) | 0.090 (3) | 0.068 (2) | 0.0091 (18) | −0.0196 (17) | −0.0150 (19) |
C32 | 0.0352 (14) | 0.0394 (14) | 0.0409 (14) | −0.0020 (11) | −0.0024 (11) | −0.0016 (11) |
C33 | 0.0418 (15) | 0.0526 (16) | 0.0379 (14) | 0.0072 (12) | −0.0043 (12) | −0.0059 (12) |
C34 | 0.0431 (16) | 0.077 (2) | 0.0449 (16) | 0.0075 (15) | 0.0045 (13) | 0.0064 (15) |
C35 | 0.0513 (18) | 0.070 (2) | 0.0541 (18) | −0.0158 (16) | −0.0105 (15) | 0.0211 (16) |
C36 | 0.068 (2) | 0.0455 (16) | 0.0504 (17) | −0.0169 (15) | −0.0076 (15) | 0.0072 (13) |
C37 | 0.0547 (17) | 0.0388 (14) | 0.0441 (15) | −0.0022 (12) | 0.0050 (13) | −0.0009 (12) |
C38 | 0.0399 (15) | 0.0416 (14) | 0.0378 (14) | 0.0021 (12) | 0.0011 (12) | −0.0016 (11) |
C39 | 0.0452 (16) | 0.0491 (16) | 0.0571 (17) | 0.0001 (13) | −0.0043 (13) | −0.0162 (13) |
C40 | 0.076 (2) | 0.0602 (19) | 0.0578 (19) | 0.0018 (17) | −0.0152 (17) | −0.0145 (15) |
C41 | 0.0374 (14) | 0.0478 (15) | 0.0421 (15) | −0.0052 (12) | −0.0010 (12) | −0.0033 (12) |
C42 | 0.0441 (15) | 0.0633 (18) | 0.0442 (15) | 0.0039 (14) | −0.0061 (13) | −0.0134 (13) |
C43 | 0.0410 (16) | 0.077 (2) | 0.066 (2) | 0.0029 (15) | −0.0003 (14) | −0.0306 (17) |
C44 | 0.0497 (18) | 0.083 (2) | 0.059 (2) | −0.0124 (17) | 0.0142 (15) | −0.0242 (17) |
C45 | 0.061 (2) | 0.076 (2) | 0.0401 (16) | −0.0208 (17) | 0.0019 (15) | −0.0080 (15) |
C46 | 0.0440 (15) | 0.0582 (17) | 0.0440 (16) | −0.0073 (13) | −0.0012 (13) | −0.0012 (13) |
O3 | 0.0422 (11) | 0.0507 (12) | 0.0963 (17) | −0.0131 (10) | −0.0086 (11) | 0.0009 (11) |
O4 | 0.0453 (11) | 0.0564 (12) | 0.0540 (11) | 0.0051 (9) | 0.0069 (9) | −0.0139 (9) |
N4 | 0.0321 (11) | 0.0354 (11) | 0.0456 (12) | −0.0013 (9) | 0.0040 (9) | −0.0003 (9) |
N5 | 0.0318 (11) | 0.0397 (12) | 0.0528 (13) | −0.0015 (9) | −0.0021 (10) | −0.0044 (10) |
N6 | 0.0360 (12) | 0.0512 (13) | 0.0410 (12) | 0.0003 (10) | −0.0020 (10) | −0.0108 (10) |
C1—C2 | 1.390 (4) | C24—C25 | 1.390 (4) |
C1—C6 | 1.510 (4) | C24—C29 | 1.509 (4) |
C1—N1 | 1.340 (3) | C24—N4 | 1.343 (3) |
C2—C3 | 1.387 (4) | C25—C26 | 1.377 (4) |
C2—H21 | 0.942 | C25—H251 | 0.939 |
C3—C4 | 1.376 (4) | C26—C27 | 1.375 (4) |
C3—H31 | 0.948 | C26—H261 | 0.950 |
C4—C5 | 1.385 (4) | C27—C28 | 1.385 (4) |
C4—H41 | 0.944 | C27—H271 | 0.923 |
C5—C15 | 1.502 (4) | C28—C38 | 1.498 (4) |
C5—N1 | 1.349 (3) | C28—N4 | 1.344 (3) |
C6—O1 | 1.233 (3) | C29—O3 | 1.240 (3) |
C6—N2 | 1.352 (3) | C29—N5 | 1.349 (3) |
C7—C8 | 1.502 (4) | C30—C31 | 1.513 (4) |
C7—N2 | 1.475 (3) | C30—N5 | 1.482 (3) |
C7—H71 | 0.987 | C30—H301 | 0.992 |
C7—H72 | 0.983 | C30—H302 | 0.975 |
C8—H83 | 0.971 | C31—H311 | 0.971 |
C8—H82 | 0.975 | C31—H313 | 0.972 |
C8—H81 | 0.966 | C31—H312 | 0.985 |
C9—C10 | 1.389 (4) | C32—C33 | 1.375 (4) |
C9—C14 | 1.384 (4) | C32—C37 | 1.392 (4) |
C9—N2 | 1.438 (3) | C32—N5 | 1.436 (3) |
C10—C11 | 1.384 (4) | C33—C34 | 1.392 (4) |
C10—H101 | 0.952 | C33—H331 | 0.924 |
C11—C12 | 1.380 (5) | C34—C35 | 1.368 (5) |
C11—H111 | 0.943 | C34—H341 | 0.944 |
C12—C13 | 1.374 (4) | C35—C36 | 1.376 (5) |
C12—H121 | 0.938 | C35—H351 | 0.942 |
C13—C14 | 1.384 (4) | C36—C37 | 1.379 (4) |
C13—H131 | 0.955 | C36—H361 | 0.930 |
C14—H141 | 0.952 | C37—H371 | 0.953 |
C15—O2 | 1.235 (3) | C38—O4 | 1.229 (3) |
C15—N3 | 1.357 (3) | C38—N6 | 1.364 (3) |
C16—C17 | 1.502 (4) | C39—C40 | 1.507 (4) |
C16—N3 | 1.480 (3) | C39—N6 | 1.481 (3) |
C16—H161 | 0.983 | C39—H391 | 0.970 |
C16—H162 | 0.978 | C39—H392 | 0.975 |
C17—H173 | 0.981 | C40—H403 | 0.992 |
C17—H172 | 0.970 | C40—H402 | 0.985 |
C17—H171 | 0.972 | C40—H401 | 0.982 |
C18—C19 | 1.379 (4) | C41—C42 | 1.387 (4) |
C18—C23 | 1.373 (4) | C41—C46 | 1.383 (4) |
C18—N3 | 1.444 (3) | C41—N6 | 1.428 (3) |
C19—C20 | 1.388 (4) | C42—C43 | 1.383 (4) |
C19—H191 | 0.949 | C42—H421 | 0.936 |
C20—C21 | 1.376 (5) | C43—C44 | 1.376 (5) |
C20—H201 | 0.939 | C43—H431 | 0.950 |
C21—C22 | 1.372 (5) | C44—C45 | 1.388 (5) |
C21—H211 | 0.935 | C44—H441 | 0.947 |
C22—C23 | 1.377 (4) | C45—C46 | 1.384 (4) |
C22—H221 | 0.949 | C45—H451 | 0.944 |
C23—H231 | 0.937 | C46—H461 | 0.938 |
C2—C1—C6 | 117.6 (2) | C25—C24—C29 | 119.5 (2) |
C2—C1—N1 | 123.1 (2) | C25—C24—N4 | 123.2 (2) |
C6—C1—N1 | 119.1 (2) | C29—C24—N4 | 117.1 (2) |
C1—C2—C3 | 119.0 (3) | C24—C25—C26 | 118.5 (3) |
C1—C2—H21 | 120.2 | C24—C25—H251 | 120.9 |
C3—C2—H21 | 120.8 | C26—C25—H251 | 120.6 |
C2—C3—C4 | 118.3 (2) | C25—C26—C27 | 119.3 (3) |
C2—C3—H31 | 122.4 | C25—C26—H261 | 120.3 |
C4—C3—H31 | 119.3 | C27—C26—H261 | 120.5 |
C3—C4—C5 | 119.4 (2) | C26—C27—C28 | 118.8 (3) |
C3—C4—H41 | 120.5 | C26—C27—H271 | 120.0 |
C5—C4—H41 | 120.1 | C28—C27—H271 | 121.2 |
C4—C5—C15 | 122.5 (2) | C27—C28—C38 | 122.1 (2) |
C4—C5—N1 | 123.0 (2) | C27—C28—N4 | 123.1 (2) |
C15—C5—N1 | 114.1 (2) | C38—C28—N4 | 114.5 (2) |
C1—C6—O1 | 117.9 (2) | C24—C29—O3 | 118.3 (2) |
C1—C6—N2 | 119.4 (2) | C24—C29—N5 | 118.8 (2) |
O1—C6—N2 | 122.7 (2) | O3—C29—N5 | 122.8 (2) |
C8—C7—N2 | 112.2 (2) | C31—C30—N5 | 111.6 (2) |
C8—C7—H71 | 107.9 | C31—C30—H301 | 108.9 |
N2—C7—H71 | 107.6 | N5—C30—H301 | 109.0 |
C8—C7—H72 | 110.0 | C31—C30—H302 | 110.6 |
N2—C7—H72 | 107.5 | N5—C30—H302 | 109.1 |
H71—C7—H72 | 111.6 | H301—C30—H302 | 107.6 |
C7—C8—H83 | 110.9 | C30—C31—H311 | 109.5 |
C7—C8—H82 | 108.6 | C30—C31—H313 | 109.2 |
H83—C8—H82 | 108.5 | H311—C31—H313 | 109.0 |
C7—C8—H81 | 110.5 | C30—C31—H312 | 110.0 |
H83—C8—H81 | 109.9 | H311—C31—H312 | 109.8 |
H82—C8—H81 | 108.4 | H313—C31—H312 | 109.2 |
C10—C9—C14 | 120.0 (3) | C33—C32—C37 | 119.8 (3) |
C10—C9—N2 | 119.4 (2) | C33—C32—N5 | 120.7 (2) |
C14—C9—N2 | 120.6 (2) | C37—C32—N5 | 119.5 (2) |
C9—C10—C11 | 119.5 (3) | C32—C33—C34 | 120.3 (3) |
C9—C10—H101 | 120.5 | C32—C33—H331 | 119.2 |
C11—C10—H101 | 120.0 | C34—C33—H331 | 120.4 |
C10—C11—C12 | 120.6 (3) | C33—C34—C35 | 119.5 (3) |
C10—C11—H111 | 120.4 | C33—C34—H341 | 119.0 |
C12—C11—H111 | 119.0 | C35—C34—H341 | 121.5 |
C11—C12—C13 | 119.5 (3) | C34—C35—C36 | 120.5 (3) |
C11—C12—H121 | 120.9 | C34—C35—H351 | 119.6 |
C13—C12—H121 | 119.6 | C36—C35—H351 | 119.9 |
C12—C13—C14 | 120.8 (3) | C35—C36—C37 | 120.4 (3) |
C12—C13—H131 | 120.8 | C35—C36—H361 | 120.0 |
C14—C13—H131 | 118.4 | C37—C36—H361 | 119.7 |
C13—C14—C9 | 119.5 (3) | C32—C37—C36 | 119.4 (3) |
C13—C14—H141 | 121.2 | C32—C37—H371 | 120.3 |
C9—C14—H141 | 119.3 | C36—C37—H371 | 120.2 |
C5—C15—O2 | 119.2 (2) | C28—C38—O4 | 119.6 (2) |
C5—C15—N3 | 119.6 (2) | C28—C38—N6 | 118.8 (2) |
O2—C15—N3 | 121.1 (2) | O4—C38—N6 | 121.5 (2) |
C17—C16—N3 | 111.8 (2) | C40—C39—N6 | 112.8 (2) |
C17—C16—H161 | 109.0 | C40—C39—H391 | 111.7 |
N3—C16—H161 | 109.7 | N6—C39—H391 | 108.6 |
C17—C16—H162 | 108.6 | C40—C39—H392 | 110.7 |
N3—C16—H162 | 108.4 | N6—C39—H392 | 107.7 |
H161—C16—H162 | 109.2 | H391—C39—H392 | 105.0 |
C16—C17—H173 | 110.4 | C39—C40—H403 | 109.2 |
C16—C17—H172 | 110.8 | C39—C40—H402 | 109.3 |
H173—C17—H172 | 108.5 | H403—C40—H402 | 109.6 |
C16—C17—H171 | 109.1 | C39—C40—H401 | 109.3 |
H173—C17—H171 | 108.8 | H403—C40—H401 | 110.3 |
H172—C17—H171 | 109.2 | H402—C40—H401 | 109.2 |
C19—C18—C23 | 120.4 (3) | C42—C41—C46 | 119.9 (3) |
C19—C18—N3 | 120.9 (2) | C42—C41—N6 | 119.7 (2) |
C23—C18—N3 | 118.6 (2) | C46—C41—N6 | 120.3 (2) |
C18—C19—C20 | 118.8 (3) | C41—C42—C43 | 120.6 (3) |
C18—C19—H191 | 120.5 | C41—C42—H421 | 119.2 |
C20—C19—H191 | 120.7 | C43—C42—H421 | 120.3 |
C19—C20—C21 | 120.9 (3) | C42—C43—C44 | 119.7 (3) |
C19—C20—H201 | 119.2 | C42—C43—H431 | 121.1 |
C21—C20—H201 | 119.8 | C44—C43—H431 | 119.2 |
C20—C21—C22 | 119.3 (3) | C43—C44—C45 | 119.9 (3) |
C20—C21—H211 | 120.4 | C43—C44—H441 | 119.9 |
C22—C21—H211 | 120.4 | C45—C44—H441 | 120.3 |
C21—C22—C23 | 120.5 (3) | C44—C45—C46 | 120.6 (3) |
C21—C22—H221 | 119.6 | C44—C45—H451 | 119.8 |
C23—C22—H221 | 119.9 | C46—C45—H451 | 119.6 |
C22—C23—C18 | 120.0 (3) | C45—C46—C41 | 119.4 (3) |
C22—C23—H231 | 120.1 | C45—C46—H461 | 120.5 |
C18—C23—H231 | 119.9 | C41—C46—H461 | 120.2 |
C16—N3—C18 | 117.2 (2) | C28—N4—C24 | 117.1 (2) |
C16—N3—C15 | 118.9 (2) | C30—N5—C32 | 117.3 (2) |
C18—N3—C15 | 123.4 (2) | C30—N5—C29 | 118.7 (2) |
C5—N1—C1 | 117.1 (2) | C32—N5—C29 | 123.1 (2) |
C7—N2—C9 | 118.0 (2) | C39—N6—C41 | 117.7 (2) |
C7—N2—C6 | 118.2 (2) | C39—N6—C38 | 118.1 (2) |
C9—N2—C6 | 123.5 (2) | C41—N6—C38 | 124.1 (2) |
C2—C1—N1—C5 | −2.0 (4) | C25—C24—N4—C28 | 2.0 (4) |
C6—C1—N1—C5 | −176.5 (2) | C29—C24—N4—C28 | 176.6 (2) |
N1—C1—C2—C3 | 2.5 (4) | N4—C24—C25—C26 | −1.8 (4) |
C6—C1—C2—C3 | 177.1 (2) | C29—C24—C25—C26 | −176.3 (2) |
N1—C1—C6—O1 | 134.1 (3) | N4—C24—C29—O3 | −132.6 (3) |
N1—C1—C6—N2 | −44.9 (3) | N4—C24—C29—N5 | 43.5 (3) |
C2—C1—C6—O1 | −40.8 (4) | C25—C24—C29—O3 | 42.3 (4) |
C2—C1—C6—N2 | 140.3 (3) | C25—C24—C29—N5 | −141.7 (3) |
C1—C2—C3—C4 | −0.5 (4) | C24—C25—C26—C27 | 0.4 (4) |
C2—C3—C4—C5 | −1.8 (4) | C25—C26—C27—C28 | 0.7 (4) |
C3—C4—C5—N1 | 2.4 (4) | C26—C27—C28—N4 | −0.5 (4) |
C3—C4—C5—C15 | −169.7 (2) | C26—C27—C28—C38 | 173.4 (2) |
C4—C5—N1—C1 | −0.5 (4) | C27—C28—N4—C24 | −0.8 (4) |
C15—C5—N1—C1 | 172.2 (2) | C38—C28—N4—C24 | −175.2 (2) |
N1—C5—C15—O2 | −46.8 (3) | N4—C28—C38—O4 | 51.2 (3) |
N1—C5—C15—N3 | 136.0 (2) | N4—C28—C38—N6 | −131.1 (2) |
C4—C5—C15—O2 | 125.9 (3) | C27—C28—C38—O4 | −123.2 (3) |
C4—C5—C15—N3 | −51.2 (3) | C27—C28—C38—N6 | 54.5 (3) |
O1—C6—N2—C7 | −4.1 (4) | O3—C29—N5—C30 | 3.4 (4) |
O1—C6—N2—C9 | 169.7 (2) | O3—C29—N5—C32 | −165.3 (3) |
C1—C6—N2—C7 | 174.8 (2) | C24—C29—N5—C30 | −172.4 (2) |
C1—C6—N2—C9 | −11.4 (4) | C24—C29—N5—C32 | 18.9 (4) |
C8—C7—N2—C6 | 96.7 (3) | C31—C30—N5—C29 | −90.4 (3) |
C8—C7—N2—C9 | −77.4 (3) | C31—C30—N5—C32 | 78.9 (3) |
C10—C9—N2—C6 | 130.0 (3) | C33—C32—N5—C29 | 53.8 (4) |
C10—C9—N2—C7 | −56.2 (3) | C33—C32—N5—C30 | −115.1 (3) |
C14—C9—N2—C6 | −51.7 (4) | C37—C32—N5—C29 | −128.1 (3) |
C14—C9—N2—C7 | 122.1 (3) | C37—C32—N5—C30 | 63.1 (3) |
N2—C9—C10—C11 | −178.6 (2) | N5—C32—C33—C34 | −179.0 (2) |
C14—C9—C10—C11 | 3.1 (4) | C37—C32—C33—C34 | 2.8 (4) |
N2—C9—C14—C13 | 178.3 (2) | N5—C32—C37—C36 | 178.4 (2) |
C10—C9—C14—C13 | −3.4 (4) | C33—C32—C37—C36 | −3.4 (4) |
C9—C10—C11—C12 | −0.5 (4) | C32—C33—C34—C35 | −0.3 (4) |
C10—C11—C12—C13 | −1.6 (4) | C33—C34—C35—C36 | −1.7 (4) |
C11—C12—C13—C14 | 1.3 (4) | C34—C35—C36—C37 | 1.0 (5) |
C12—C13—C14—C9 | 1.2 (4) | C35—C36—C37—C32 | 1.6 (4) |
O2—C15—N3—C16 | 0.6 (4) | O4—C38—N6—C39 | 4.1 (4) |
O2—C15—N3—C18 | 172.3 (2) | O4—C38—N6—C41 | −171.5 (2) |
C5—C15—N3—C16 | 177.8 (2) | C28—C38—N6—C39 | −173.7 (2) |
C5—C15—N3—C18 | −10.6 (4) | C28—C38—N6—C41 | 10.7 (4) |
C17—C16—N3—C15 | 86.6 (3) | C40—C39—N6—C38 | 79.6 (3) |
C17—C16—N3—C18 | −85.7 (3) | C40—C39—N6—C41 | −104.5 (3) |
C19—C18—N3—C15 | −60.3 (3) | C42—C41—N6—C38 | −130.0 (3) |
C19—C18—N3—C16 | 111.5 (3) | C42—C41—N6—C39 | 54.3 (3) |
C23—C18—N3—C15 | 122.4 (3) | C46—C41—N6—C38 | 54.1 (3) |
C23—C18—N3—C16 | −65.8 (3) | C46—C41—N6—C39 | −121.5 (3) |
N3—C18—C19—C20 | −178.3 (3) | N6—C41—C42—C43 | −176.7 (3) |
C23—C18—C19—C20 | −1.0 (4) | C46—C41—C42—C43 | −0.8 (4) |
N3—C18—C23—C22 | 177.7 (3) | N6—C41—C46—C45 | 177.9 (3) |
C19—C18—C23—C22 | 0.4 (4) | C42—C41—C46—C45 | 2.1 (4) |
C18—C19—C20—C21 | 1.2 (5) | C41—C42—C43—C44 | −0.6 (5) |
C19—C20—C21—C22 | −0.7 (5) | C42—C43—C44—C45 | 0.7 (5) |
C20—C21—C22—C23 | 0.0 (5) | C43—C44—C45—C46 | 0.6 (5) |
C21—C22—C23—C18 | 0.2 (5) | C44—C45—C46—C41 | −2.0 (5) |
N1—C1—C2—H21 | −178 | N4—C24—C25—H251 | 178 |
C6—C1—C2—H21 | −4 | C29—C24—C25—H251 | 3 |
C1—C2—C3—H31 | 179 | C24—C25—C26—H261 | −179 |
H21—C2—C3—C4 | −180 | H251—C25—C26—C27 | −179 |
H21—C2—C3—H31 | 0 | H251—C25—C26—H261 | 1 |
C2—C3—C4—H41 | −179 | C25—C26—C27—H271 | −180 |
H31—C3—C4—C5 | 179 | H261—C26—C27—C28 | −179 |
H31—C3—C4—H41 | 1 | H261—C26—C27—H271 | 0 |
H41—C4—C5—N1 | 180 | H271—C27—C28—N4 | 180 |
H41—C4—C5—C15 | 8 | H271—C27—C28—C38 | −6 |
H71—C7—N2—C6 | −145 | H301—C30—N5—C29 | 149 |
H71—C7—N2—C9 | 41 | H301—C30—N5—C32 | −41 |
H72—C7—N2—C6 | −24 | H302—C30—N5—C29 | 32 |
H72—C7—N2—C9 | 161 | H302—C30—N5—C32 | −159 |
N2—C7—C8—H81 | −62 | N5—C30—C31—H311 | 179 |
N2—C7—C8—H82 | 57 | N5—C30—C31—H312 | 58 |
N2—C7—C8—H83 | 176 | N5—C30—C31—H313 | −62 |
H71—C7—C8—H81 | 180 | H301—C30—C31—H311 | −61 |
H71—C7—C8—H82 | −62 | H301—C30—C31—H312 | 178 |
H71—C7—C8—H83 | 58 | H301—C30—C31—H313 | 59 |
H72—C7—C8—H81 | 58 | H302—C30—C31—H311 | 57 |
H72—C7—C8—H82 | 177 | H302—C30—C31—H312 | −63 |
H72—C7—C8—H83 | −64 | H302—C30—C31—H313 | 177 |
N2—C9—C10—H101 | 0 | N5—C32—C33—H331 | 0 |
C14—C9—C10—H101 | −179 | C37—C32—C33—H331 | −178 |
N2—C9—C14—H141 | −1 | N5—C32—C37—H371 | −1 |
C10—C9—C14—H141 | 177 | C33—C32—C37—H371 | 178 |
C9—C10—C11—H111 | 178 | C32—C33—C34—H341 | −179 |
H101—C10—C11—C12 | −179 | H331—C33—C34—C35 | −179 |
H101—C10—C11—H111 | −1 | H331—C33—C34—H341 | 2 |
C10—C11—C12—H121 | 180 | C33—C34—C35—H351 | −180 |
H111—C11—C12—C13 | −180 | H341—C34—C35—C36 | 178 |
H111—C11—C12—H121 | 2 | H341—C34—C35—H351 | −1 |
C11—C12—C13—H131 | −178 | C34—C35—C36—H361 | −178 |
H121—C12—C13—C14 | 180 | H351—C35—C36—C37 | 179 |
H121—C12—C13—H131 | 1 | H351—C35—C36—H361 | 0 |
C12—C13—C14—H141 | −179 | C35—C36—C37—H371 | −179 |
H131—C13—C14—C9 | −179 | H361—C36—C37—C32 | −179 |
H131—C13—C14—H141 | 0 | H361—C36—C37—H371 | 0 |
H161—C16—N3—C15 | −35 | H391—C39—N6—C38 | −45 |
H161—C16—N3—C18 | 153 | H391—C39—N6—C41 | 131 |
H162—C16—N3—C15 | −154 | H392—C39—N6—C38 | −158 |
H162—C16—N3—C18 | 34 | H392—C39—N6—C41 | 18 |
N3—C16—C17—H171 | 55 | N6—C39—C40—H401 | 52 |
N3—C16—C17—H172 | −65 | N6—C39—C40—H402 | −67 |
N3—C16—C17—H173 | 174 | N6—C39—C40—H403 | 173 |
H161—C16—C17—H171 | 176 | H391—C39—C40—H401 | 175 |
H161—C16—C17—H172 | 56 | H391—C39—C40—H402 | 55 |
H161—C16—C17—H173 | −64 | H391—C39—C40—H403 | −65 |
H162—C16—C17—H171 | −65 | H392—C39—C40—H401 | −69 |
H162—C16—C17—H172 | 175 | H392—C39—C40—H402 | 172 |
H162—C16—C17—H173 | 55 | H392—C39—C40—H403 | 52 |
N3—C18—C19—H191 | 2 | N6—C41—C42—H421 | 4 |
C23—C18—C19—H191 | 179 | C46—C41—C42—H421 | 180 |
N3—C18—C23—H231 | −1 | N6—C41—C46—H461 | −2 |
C19—C18—C23—H231 | −179 | C42—C41—C46—H461 | −178 |
C18—C19—C20—H201 | −178 | C41—C42—C43—H431 | 177 |
H191—C19—C20—C21 | −179 | H421—C42—C43—C44 | 179 |
H191—C19—C20—H201 | 2 | H421—C42—C43—H431 | −4 |
C19—C20—C21—H211 | 179 | C42—C43—C44—H441 | −179 |
H201—C20—C21—C22 | 178 | H431—C43—C44—C45 | −177 |
H201—C20—C21—H211 | −2 | H431—C43—C44—H441 | 3 |
C20—C21—C22—H221 | 179 | C43—C44—C45—H451 | −179 |
H211—C21—C22—C23 | −180 | H441—C44—C45—C46 | −180 |
H211—C21—C22—H221 | −1 | H441—C44—C45—H451 | 0 |
C21—C22—C23—H231 | 179 | C44—C45—C46—H461 | 178 |
H221—C22—C23—C18 | −179 | H451—C45—C46—C41 | 178 |
H221—C22—C23—H231 | 0 | H451—C45—C46—H461 | −2 |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H341···O1i | 0.94 | 2.42 | 3.319 (4) | 159 |
C42—H421···O2ii | 0.94 | 2.43 | 3.271 (4) | 150 |
C7—H71···O2ii | 0.99 | 2.40 | 3.208 (4) | 138 |
C43—H431···O3iii | 0.95 | 2.66 | 3.443 (4) | 140 |
C30—H301···O4iv | 0.99 | 2.36 | 3.237 (4) | 147 |
C23—H231···O4v | 0.94 | 2.60 | 3.125 (3) | 116 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z; (iv) −x, −y+2, −z+1; (v) −x, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C23H23N3O2 |
Mr | 373.45 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 170 |
a, b, c (Å) | 12.1879 (17), 12.2371 (15), 13.6798 (17) |
α, β, γ (°) | 83.971 (10), 86.919 (11), 87.744 (10) |
V (Å3) | 2024.9 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.63 |
Crystal size (mm) | 0.37 × 0.19 × 0.15 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.496, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 51216, 8553, 4586 |
Rint | 0.111 |
(sin θ/λ)max (Å−1) | 0.647 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.062, 1.14 |
No. of reflections | 4586 |
No. of parameters | 505 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.25 |
Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), Mercury (Macrae et al., 2006), CRYSTALS (Betteridge et al., 2003), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H341···O1i | 0.944 | 2.419 | 3.319 (4) | 159.24 |
C42—H421···O2ii | 0.936 | 2.430 | 3.271 (4) | 149.57 |
C7—H71···O2ii | 0.987 | 2.403 | 3.208 (4) | 138.29 |
C43—H431···O3iii | 0.950 | 2.662 | 3.443 (4) | 139.78 |
C30—H301···O4iv | 0.992 | 2.361 | 3.237 (4) | 146.77 |
C23—H231···O4v | 0.938 | 2.595 | 3.125 (3) | 116.21 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z; (iv) −x, −y+2, −z+1; (v) −x, −y+1, −z+2. |
Acknowledgements
This work was supported by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, project No. 42900/1312/3114 "Environmental Aspects of Sustainable Development of Society".
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyridine-dicarboxamides have been studied recently for significant extractive properties (Alyapyshev et al., 2004). The factors which lead to stabilization of low symmetry five-coordinate complexes, when using neutral donor ligands, have been reported (Du Preez et al., 1987).
The title compound crystallizes with two independent molecules (1 and 2) (Figs. 1 & 2) in an asymmetric unit. The molecules consist of a pyridine ring between two amide groups in the ortho positions of this ring and ethyl and phenyl groups on the amide nitrogen. Both molecules in the asymmetric unit adopt a syn-anti conformation, in contrast to the syn-syn conformation found in N,N'-diphenylpyridine-2,6-dicarboxamide (Malone et al., 1997), but analogous to that observed in N,N'-dimethyl-N,N'-diphenylpyridine-2,6-dicarboxamide (Fujiwara et al., 2008).
There are minor conformational differences in the two molecules as reflected in the torsion angles Npyridine—C—C—Namide being -44.9 (3) and 136.0 (2)° for molecule 1 and 43.5 (3) and -131.1 (2)° for molecule 2 and the torsion angles Npyridine—C—C—Oamide being 134.1 (3) and -46.8 (3)° for molecule 1 and -132.6 (3) and 51.2 (3)° for molecule 2. However, the two molecules show significant differences in the orientation of an ethyl group (the corresponding torsion angles are C17—C16—N3—C15 86.6 (3)° for molecule 1 and C40—C39—N6—C38 79.6 (3)° for molecule 2).
The molecules are connected via weak intermolecular C—H···O interactions between the amide oxygen atoms and ethyl and phenyl groups, forming a three-dimensional network (Fig. 3).