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N-[2-(4-Methyl-2-quinolyl)phenyl]acetamide: a P1 structure with Z = 4
aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
The title compound, C18H16N2O, crystallizes in the triclinic P1, with four independent molecules in the wherein two molecules have an irregular -ac, -ac, +ap conformation (ap, antiperiplanar; ac, anticlinal), while the other molecules exhibit a different, +ac, +ac, +ap conformation. The planar (r.m.s. deviation = 0.006 Å in each of the four molecules) quinoline ring systems of the four molecules are oriented at dihedral angles of 32.8 (2), 33.4 (2), 31.7 (2) and 32.3 (2)° with respect to the benzene rings. Intramolecular N—H⋯N interactions occur in all four independent molecules. The crystal packing is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds, and are further consolidated by C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.728 (3), 3.722 (3), 3.758 (3) and 3.705 (3) Å].
Related literature
For the biological activity of quinolines, see: Roopan & Khan (2009); Roopan et al. (2010
); Yates (1984
). For the crystal structures of substituted quinolines, see: Khan et al. (2010
); Kushwaha et al. (2010
); Subashini et al. (2009
). For another with Z′ = 4 in P1, see: Bernès et al. (2003
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
); software used to prepare material for publication: WinGX (Farrugia, 1999
).
Supporting information
https://doi.org/10.1107/S1600536810027650/pv2303sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027650/pv2303Isup2.hkl
About 1 mmol of 2-aminoacetophenone in 10 ml of glacial acetic acid and 2 drops of concentrated sulfuric acid were refluxed at 393 K for 8 h. After the completion of the reaction (monitored by TLC) the mixture was poured in to crushed ice to afford the crude product which was purified by
on silica gel. The pure compound was dissolved in ethanol to get single crystals.An analysis of the E-statistics indicated the structure to be non-centrosymmetric. The centrosymmetric
P -1 was attempted but it was not successful. However, the crystal was twinned and TWIN and BASF instructions were used in the procedure. The H atoms were positioned geometrically with N—H = 0.86 Å, C—H = 0.93 and 0.96 Å, and refined a riding model, with Uiso(H) = 1.2–1.5Ueq(C). In the absence of significant effects, Freidel pairs were merged using the MERG 4 command in SHELXL97; Sheldrick, 2008).Quinolines and their derivatives occur in numerous natural products, many of which possess interesting physiological and biological properties. Quinoline derivatives have been developed for the treatment of many diseases like malaria, HIV, tumor, and antibacterial infections (Yates, 1984). Since the turn of the century, the development of concise and effective methodologies for the preparation of libraries of small molecules for research in drug discovery has remained a major challenge. A number of strategies have been developed to address this challenge (Roopan et al., 2009, Roopan et al., 2010). We herewith reporting the synthesis of 2-substituted quinoline using 1-(2-aminophenyl)ethanone in acetic acid and drop of sulphuric acid at 453 K.
The title compound crystallizes in the triclinic
P 1 with four independent molecules, A, B, C and D with O1, O2, O3 and O4, respectively, in the (Figs. 1-4) with no evidence of pseudo- or Crystals belonging to this class, namely Z' = 4 in P 1, are not uncommon (Bernés et al., 2003). The molecules A and B have an irregular -ac, -ac, +ap conformation (C2-C1-C11-C16, C11-C16-N2-C17, C16-N2-C17-C18 in molecule A and C20-C19-C29-C34, C29-C34-N4-C35, C34-N4-C35-C36 in molecule B) while the other molecules C and D exhibit a different, +ac, +ac, +ap conformation (C38-C37-C47-C52, C47-C52-N6-C53, C52-N6-C53-C54 in molecule C and C56-C55-C65-C70, C65-C70-N8-C71, C70-N8-C71-C72 in molecule D). The planar quinoline ring system of each molecule makes a dihedral angle of 32.8 (2)° for A, 33.4 (2)° for B, 31.7 (2)° for C and 32.3 (2)° for D with the benzene ring [C11–C16 for A, C29–C34 for B, C47–C52 for C and C65–C70 for D] bound to it.The crystal packing is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 5), and are further consolidated by C—H···π (Table 1) and π-π stacking interactions [Cg1···Cg14(x, -1 + y, z) = 3.728 (3), Cg2···Cg13 (1 + x, -1 + y, z) = 3.722 (3), Cg5···Cg10(-1 + x, y, z) = 3.758 (3), Cg6···Cg9(x, y, z) = 3.705 (3) Å; where Cg1, Cg2, Cg5, Cg6, Cg9, Cg10, Cg13 and Cg14 are the centroids of N1/C1–C4/C9, C4–C9, N3/C19–C22/C27, C22–C27, N5/C37–C40/C45, C40–C45, N7/C55–C58/C63 and C58–C63 rings, respectively].
For the biological activity of quinolines, see: Roopan & Khan (2009); Roopan et al. (2010); Yates (1984). For the crystal structures of substituted quinolines, see: Khan et al. (2010); Kushwaha et al. (2010); Subashini et al. (2009). For a
with Z' = 4 in P1, see: Bernès et al. (2003).Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell
CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C18H16N2O | Z = 4 |
Mr = 276.33 | F(000) = 584 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7383 (5) Å | Cell parameters from 1432 reflections |
b = 9.9035 (6) Å | θ = 2.0–20.5° |
c = 15.2809 (9) Å | µ = 0.08 mm−1 |
α = 101.414 (5)° | T = 295 K |
β = 99.188 (5)° | Block, colourless |
γ = 90.065 (5)° | 0.20 × 0.10 × 0.10 mm |
V = 1425.24 (14) Å3 |
Oxford Xcalibur Eos(Nova) CCD detector diffractometer | 5290 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3314 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | h = −11→11 |
Tmin = 0.984, Tmax = 0.992 | k = −11→11 |
29328 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.1055P)2] where P = (Fo2 + 2Fc2)/3 |
5290 reflections | (Δ/σ)max < 0.001 |
766 parameters | Δρmax = 0.23 e Å−3 |
3 restraints | Δρmin = −0.24 e Å−3 |
C18H16N2O | γ = 90.065 (5)° |
Mr = 276.33 | V = 1425.24 (14) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7383 (5) Å | Mo Kα radiation |
b = 9.9035 (6) Å | µ = 0.08 mm−1 |
c = 15.2809 (9) Å | T = 295 K |
α = 101.414 (5)° | 0.20 × 0.10 × 0.10 mm |
β = 99.188 (5)° |
Oxford Xcalibur Eos(Nova) CCD detector diffractometer | 5290 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | 3314 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.992 | Rint = 0.079 |
29328 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 3 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.23 e Å−3 |
5290 reflections | Δρmin = −0.24 e Å−3 |
766 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5433 (4) | 0.3283 (5) | −0.0893 (3) | 0.0679 (16) | |
N1 | 0.9301 (5) | 0.0670 (5) | 0.0014 (3) | 0.0477 (17) | |
N2 | 0.7568 (5) | 0.2789 (5) | −0.0233 (3) | 0.0479 (17) | |
C1 | 0.8509 (5) | 0.0467 (6) | 0.0608 (4) | 0.0447 (19) | |
C2 | 0.8302 (6) | −0.0875 (6) | 0.0787 (4) | 0.049 (2) | |
C3 | 0.8889 (5) | −0.2001 (6) | 0.0339 (4) | 0.050 (2) | |
C4 | 0.9720 (5) | −0.1799 (6) | −0.0317 (4) | 0.0468 (19) | |
C5 | 1.0340 (6) | −0.2906 (7) | −0.0856 (4) | 0.058 (2) | |
C6 | 1.1092 (7) | −0.2636 (7) | −0.1487 (4) | 0.064 (3) | |
C7 | 1.1259 (7) | −0.1275 (7) | −0.1600 (4) | 0.063 (3) | |
C8 | 1.0672 (6) | −0.0231 (7) | −0.1108 (4) | 0.057 (2) | |
C9 | 0.9890 (5) | −0.0465 (6) | −0.0459 (4) | 0.047 (2) | |
C10 | 0.8644 (7) | −0.3407 (7) | 0.0521 (5) | 0.066 (3) | |
C11 | 0.7762 (6) | 0.1633 (5) | 0.1048 (4) | 0.0446 (17) | |
C12 | 0.7446 (7) | 0.1650 (6) | 0.1914 (4) | 0.057 (2) | |
C13 | 0.6635 (7) | 0.2636 (8) | 0.2323 (4) | 0.065 (3) | |
C14 | 0.6128 (7) | 0.3667 (7) | 0.1878 (4) | 0.062 (2) | |
C15 | 0.6434 (6) | 0.3709 (6) | 0.1040 (4) | 0.0507 (19) | |
C16 | 0.7258 (5) | 0.2726 (6) | 0.0623 (4) | 0.0442 (17) | |
C17 | 0.6659 (6) | 0.3079 (6) | −0.0933 (4) | 0.049 (2) | |
C18 | 0.7213 (6) | 0.3083 (8) | −0.1781 (4) | 0.066 (2) | |
O2 | 0.2107 (4) | 0.0456 (6) | 0.5805 (3) | 0.0728 (18) | |
N3 | 0.5519 (5) | 0.3067 (5) | 0.4898 (3) | 0.0489 (17) | |
N4 | 0.3917 (5) | 0.0960 (5) | 0.5163 (3) | 0.0500 (17) | |
C19 | 0.4453 (6) | 0.3265 (6) | 0.4306 (4) | 0.0429 (17) | |
C20 | 0.4127 (6) | 0.4601 (6) | 0.4125 (4) | 0.051 (2) | |
C21 | 0.4952 (6) | 0.5736 (6) | 0.4563 (4) | 0.0477 (19) | |
C22 | 0.6121 (5) | 0.5530 (6) | 0.5222 (4) | 0.0435 (17) | |
C23 | 0.7021 (7) | 0.6627 (7) | 0.5749 (4) | 0.059 (2) | |
C24 | 0.8104 (7) | 0.6361 (7) | 0.6365 (4) | 0.063 (3) | |
C25 | 0.8316 (6) | 0.5019 (7) | 0.6502 (4) | 0.061 (3) | |
C26 | 0.7462 (6) | 0.3954 (7) | 0.6017 (4) | 0.057 (2) | |
C27 | 0.6368 (6) | 0.4191 (5) | 0.5363 (4) | 0.0437 (17) | |
C28 | 0.4617 (7) | 0.7137 (6) | 0.4391 (5) | 0.068 (3) | |
C29 | 0.3475 (6) | 0.2082 (6) | 0.3856 (4) | 0.0465 (19) | |
C30 | 0.2745 (7) | 0.2048 (7) | 0.2995 (4) | 0.061 (2) | |
C31 | 0.1718 (7) | 0.1061 (8) | 0.2583 (5) | 0.070 (3) | |
C32 | 0.1437 (7) | 0.0043 (7) | 0.3041 (5) | 0.065 (3) | |
C33 | 0.2144 (6) | 0.0003 (6) | 0.3879 (4) | 0.0527 (19) | |
C34 | 0.3185 (5) | 0.1019 (6) | 0.4296 (4) | 0.050 (2) | |
C35 | 0.3340 (6) | 0.0675 (6) | 0.5860 (4) | 0.051 (2) | |
C36 | 0.4340 (6) | 0.0684 (8) | 0.6700 (4) | 0.066 (3) | |
O3 | 0.7086 (4) | 1.0413 (5) | 0.5781 (3) | 0.0692 (16) | |
N5 | 1.0455 (4) | 0.7212 (5) | 0.4866 (3) | 0.0451 (16) | |
N6 | 0.8859 (5) | 0.9444 (5) | 0.5108 (3) | 0.0479 (16) | |
C37 | 0.9378 (5) | 0.6617 (6) | 0.4268 (3) | 0.0423 (17) | |
C38 | 0.9110 (6) | 0.5172 (6) | 0.4096 (4) | 0.0480 (17) | |
C39 | 0.9949 (6) | 0.4330 (6) | 0.4534 (4) | 0.050 (2) | |
C40 | 1.1085 (6) | 0.4948 (6) | 0.5202 (4) | 0.0474 (19) | |
C41 | 1.1998 (7) | 0.4191 (7) | 0.5722 (4) | 0.057 (2) | |
C42 | 1.3077 (7) | 0.4881 (8) | 0.6362 (5) | 0.064 (3) | |
C43 | 1.3243 (6) | 0.6285 (8) | 0.6493 (4) | 0.064 (3) | |
C44 | 1.2377 (6) | 0.7027 (7) | 0.5996 (4) | 0.054 (2) | |
C45 | 1.1293 (5) | 0.6383 (6) | 0.5340 (4) | 0.0441 (19) | |
C46 | 0.9622 (7) | 0.2814 (7) | 0.4362 (5) | 0.069 (3) | |
C47 | 0.8399 (6) | 0.7511 (6) | 0.3819 (4) | 0.0448 (17) | |
C48 | 0.7663 (7) | 0.7020 (7) | 0.2959 (4) | 0.057 (2) | |
C49 | 0.6643 (7) | 0.7741 (8) | 0.2551 (4) | 0.067 (3) | |
C50 | 0.6357 (6) | 0.9044 (7) | 0.2999 (5) | 0.061 (3) | |
C51 | 0.7087 (6) | 0.9602 (7) | 0.3832 (4) | 0.053 (2) | |
C52 | 0.8113 (5) | 0.8866 (6) | 0.4248 (4) | 0.0446 (17) | |
C53 | 0.8323 (6) | 1.0137 (6) | 0.5815 (4) | 0.050 (2) | |
C54 | 0.9305 (7) | 1.0539 (8) | 0.6673 (4) | 0.070 (3) | |
O4 | 0.0423 (4) | 0.3327 (6) | −0.0889 (3) | 0.0733 (18) | |
N7 | 0.4267 (5) | 0.6515 (5) | 0.0017 (3) | 0.0443 (16) | |
N8 | 0.2536 (5) | 0.4286 (5) | −0.0231 (3) | 0.0471 (16) | |
C55 | 0.3477 (6) | 0.7108 (6) | 0.0610 (3) | 0.0449 (17) | |
C56 | 0.3282 (6) | 0.8550 (6) | 0.0788 (4) | 0.049 (2) | |
C57 | 0.3881 (6) | 0.9399 (6) | 0.0347 (4) | 0.0529 (19) | |
C58 | 0.4710 (5) | 0.8799 (6) | −0.0307 (4) | 0.0443 (19) | |
C59 | 0.5375 (6) | 0.9536 (7) | −0.0836 (5) | 0.060 (2) | |
C60 | 0.6132 (6) | 0.8888 (7) | −0.1453 (4) | 0.060 (3) | |
C61 | 0.6281 (6) | 0.7468 (8) | −0.1591 (4) | 0.060 (2) | |
C62 | 0.5646 (6) | 0.6722 (7) | −0.1089 (4) | 0.056 (2) | |
C63 | 0.4868 (5) | 0.7360 (6) | −0.0448 (4) | 0.0447 (19) | |
C64 | 0.3641 (7) | 1.0908 (7) | 0.0524 (5) | 0.069 (3) | |
C65 | 0.2726 (5) | 0.6201 (5) | 0.1057 (3) | 0.0419 (17) | |
C66 | 0.2424 (6) | 0.6714 (7) | 0.1922 (4) | 0.058 (2) | |
C67 | 0.1606 (7) | 0.5957 (8) | 0.2330 (4) | 0.064 (3) | |
C68 | 0.1105 (7) | 0.4662 (7) | 0.1882 (5) | 0.062 (3) | |
C69 | 0.1415 (6) | 0.4109 (6) | 0.1048 (4) | 0.0527 (19) | |
C70 | 0.2233 (5) | 0.4852 (6) | 0.0627 (4) | 0.0461 (19) | |
C71 | 0.1644 (6) | 0.3579 (6) | −0.0941 (4) | 0.050 (2) | |
C72 | 0.2186 (7) | 0.3182 (8) | −0.1798 (5) | 0.067 (3) | |
H2 | 0.77570 | −0.09830 | 0.12170 | 0.0580* | |
H2N | 0.84080 | 0.26300 | −0.03210 | 0.0580* | |
H5 | 1.02300 | −0.38050 | −0.07780 | 0.0690* | |
H6 | 1.14940 | −0.33520 | −0.18410 | 0.0770* | |
H7 | 1.17860 | −0.10960 | −0.20240 | 0.0760* | |
H8 | 1.07860 | 0.06600 | −0.11990 | 0.0680* | |
H10A | 0.93300 | −0.35620 | 0.10140 | 0.0990* | |
H10B | 0.87120 | −0.40900 | −0.00100 | 0.0990* | |
H10C | 0.77320 | −0.34690 | 0.06770 | 0.0990* | |
H12 | 0.77970 | 0.09710 | 0.22210 | 0.0680* | |
H13 | 0.64290 | 0.26120 | 0.28930 | 0.0770* | |
H14 | 0.55760 | 0.43360 | 0.21500 | 0.0750* | |
H15 | 0.60850 | 0.44050 | 0.07480 | 0.0610* | |
H18A | 0.64540 | 0.30660 | −0.22690 | 0.0980* | |
H18B | 0.77600 | 0.22850 | −0.19150 | 0.0980* | |
H18C | 0.77850 | 0.39000 | −0.17100 | 0.0980* | |
H4N | 0.48020 | 0.11190 | 0.52570 | 0.0600* | |
H20 | 0.33480 | 0.47020 | 0.37070 | 0.0620* | |
H23 | 0.68700 | 0.75260 | 0.56720 | 0.0710* | |
H24 | 0.87060 | 0.70770 | 0.66970 | 0.0750* | |
H25 | 0.90530 | 0.48520 | 0.69310 | 0.0730* | |
H26 | 0.76060 | 0.30680 | 0.61210 | 0.0680* | |
H28A | 0.37030 | 0.71110 | 0.40410 | 0.1020* | |
H28B | 0.52860 | 0.74310 | 0.40630 | 0.1020* | |
H28C | 0.46460 | 0.77720 | 0.49570 | 0.1020* | |
H30 | 0.29560 | 0.27170 | 0.26820 | 0.0730* | |
H31 | 0.12250 | 0.10780 | 0.20120 | 0.0840* | |
H32 | 0.07490 | −0.06290 | 0.27700 | 0.0780* | |
H33 | 0.19410 | −0.06910 | 0.41740 | 0.0630* | |
H36A | 0.41260 | 0.14110 | 0.71710 | 0.0980* | |
H36B | 0.52680 | 0.08330 | 0.65930 | 0.0980* | |
H36C | 0.42730 | −0.01850 | 0.68810 | 0.0980* | |
H6N | 0.97440 | 0.93430 | 0.51890 | 0.0570* | |
H38 | 0.83430 | 0.47900 | 0.36750 | 0.0580* | |
H41 | 1.18780 | 0.32400 | 0.56370 | 0.0690* | |
H42 | 1.36880 | 0.43880 | 0.67010 | 0.0780* | |
H43 | 1.39590 | 0.67370 | 0.69300 | 0.0770* | |
H44 | 1.25110 | 0.79790 | 0.60960 | 0.0650* | |
H46A | 0.88630 | 0.25780 | 0.38680 | 0.1030* | |
H46B | 0.93660 | 0.25760 | 0.48950 | 0.1030* | |
H46C | 1.04260 | 0.23170 | 0.42120 | 0.1030* | |
H48 | 0.78730 | 0.61610 | 0.26460 | 0.0690* | |
H49 | 0.61470 | 0.73650 | 0.19830 | 0.0800* | |
H50 | 0.56610 | 0.95420 | 0.27290 | 0.0740* | |
H51 | 0.68940 | 1.04830 | 0.41210 | 0.0640* | |
H54A | 0.91000 | 1.14440 | 0.69750 | 0.1050* | |
H54B | 1.02400 | 1.05440 | 0.65470 | 0.1050* | |
H54C | 0.92150 | 0.98920 | 0.70530 | 0.1050* | |
H8N | 0.33780 | 0.44010 | −0.03140 | 0.0560* | |
H56 | 0.27320 | 0.89230 | 0.12150 | 0.0590* | |
H59 | 0.52900 | 1.04860 | −0.07570 | 0.0720* | |
H60 | 0.65590 | 0.93980 | −0.17910 | 0.0710* | |
H61 | 0.68030 | 0.70290 | −0.20170 | 0.0730* | |
H62 | 0.57400 | 0.57730 | −0.11810 | 0.0670* | |
H64A | 0.29360 | 1.11030 | 0.09000 | 0.1040* | |
H64B | 0.33430 | 1.11930 | −0.00390 | 0.1040* | |
H64C | 0.44910 | 1.14000 | 0.08250 | 0.1040* | |
H66 | 0.27770 | 0.75810 | 0.22310 | 0.0690* | |
H67 | 0.13980 | 0.63210 | 0.29020 | 0.0770* | |
H68 | 0.05490 | 0.41570 | 0.21510 | 0.0740* | |
H69 | 0.10780 | 0.32280 | 0.07580 | 0.0630* | |
H72A | 0.24060 | 0.22250 | −0.18900 | 0.1010* | |
H72B | 0.30100 | 0.37300 | −0.17740 | 0.1010* | |
H72C | 0.14950 | 0.33340 | −0.22890 | 0.1010* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.037 (2) | 0.086 (3) | 0.087 (3) | 0.012 (2) | 0.013 (2) | 0.030 (3) |
N1 | 0.042 (3) | 0.044 (3) | 0.059 (3) | −0.001 (2) | 0.009 (2) | 0.014 (2) |
N2 | 0.041 (3) | 0.050 (3) | 0.056 (3) | 0.000 (2) | 0.010 (2) | 0.017 (2) |
C1 | 0.034 (3) | 0.053 (4) | 0.045 (3) | −0.003 (3) | −0.001 (2) | 0.011 (3) |
C2 | 0.040 (3) | 0.050 (4) | 0.059 (4) | 0.003 (3) | 0.007 (3) | 0.019 (3) |
C3 | 0.036 (3) | 0.051 (4) | 0.062 (4) | 0.001 (3) | −0.003 (3) | 0.021 (3) |
C4 | 0.033 (3) | 0.054 (4) | 0.050 (3) | 0.008 (3) | −0.003 (2) | 0.010 (3) |
C5 | 0.050 (4) | 0.049 (4) | 0.069 (4) | 0.010 (3) | −0.007 (3) | 0.014 (3) |
C6 | 0.064 (4) | 0.062 (5) | 0.065 (4) | 0.027 (3) | 0.014 (3) | 0.007 (3) |
C7 | 0.052 (4) | 0.071 (5) | 0.067 (4) | 0.007 (3) | 0.014 (3) | 0.015 (4) |
C8 | 0.050 (4) | 0.063 (4) | 0.061 (4) | 0.002 (3) | 0.011 (3) | 0.016 (3) |
C9 | 0.033 (3) | 0.050 (4) | 0.055 (4) | 0.007 (3) | −0.005 (3) | 0.012 (3) |
C10 | 0.059 (4) | 0.055 (4) | 0.091 (5) | 0.002 (3) | 0.009 (4) | 0.034 (4) |
C11 | 0.044 (3) | 0.038 (3) | 0.050 (3) | 0.001 (2) | 0.006 (3) | 0.006 (3) |
C12 | 0.063 (4) | 0.046 (4) | 0.059 (4) | −0.004 (3) | 0.007 (3) | 0.009 (3) |
C13 | 0.067 (4) | 0.075 (5) | 0.051 (4) | −0.010 (4) | 0.022 (3) | 0.001 (3) |
C14 | 0.060 (4) | 0.056 (4) | 0.067 (4) | −0.005 (3) | 0.025 (3) | −0.008 (3) |
C15 | 0.044 (3) | 0.036 (3) | 0.072 (4) | −0.001 (3) | 0.014 (3) | 0.007 (3) |
C16 | 0.036 (3) | 0.038 (3) | 0.057 (3) | −0.006 (2) | 0.007 (2) | 0.006 (3) |
C17 | 0.046 (4) | 0.045 (3) | 0.059 (4) | −0.003 (3) | 0.006 (3) | 0.017 (3) |
C18 | 0.047 (3) | 0.091 (5) | 0.061 (4) | 0.011 (3) | 0.011 (3) | 0.017 (3) |
O2 | 0.038 (2) | 0.097 (4) | 0.090 (3) | −0.011 (2) | 0.015 (2) | 0.031 (3) |
N3 | 0.043 (3) | 0.052 (3) | 0.056 (3) | −0.001 (2) | 0.011 (2) | 0.019 (2) |
N4 | 0.039 (3) | 0.048 (3) | 0.067 (3) | 0.004 (2) | 0.013 (2) | 0.018 (2) |
C19 | 0.042 (3) | 0.045 (3) | 0.047 (3) | 0.002 (3) | 0.018 (3) | 0.013 (3) |
C20 | 0.051 (3) | 0.051 (4) | 0.058 (4) | 0.000 (3) | 0.015 (3) | 0.021 (3) |
C21 | 0.048 (3) | 0.040 (3) | 0.064 (4) | 0.001 (3) | 0.025 (3) | 0.019 (3) |
C22 | 0.040 (3) | 0.047 (3) | 0.050 (3) | −0.003 (3) | 0.020 (3) | 0.015 (3) |
C23 | 0.056 (4) | 0.049 (4) | 0.079 (4) | −0.003 (3) | 0.027 (4) | 0.018 (3) |
C24 | 0.056 (4) | 0.069 (5) | 0.064 (4) | −0.022 (3) | 0.014 (3) | 0.011 (3) |
C25 | 0.052 (4) | 0.072 (5) | 0.059 (4) | −0.012 (3) | 0.005 (3) | 0.014 (3) |
C26 | 0.045 (3) | 0.059 (4) | 0.072 (4) | 0.002 (3) | 0.017 (3) | 0.022 (3) |
C27 | 0.044 (3) | 0.040 (3) | 0.052 (3) | −0.005 (3) | 0.020 (3) | 0.011 (3) |
C28 | 0.070 (4) | 0.048 (4) | 0.095 (5) | −0.001 (3) | 0.020 (4) | 0.030 (4) |
C29 | 0.041 (3) | 0.046 (3) | 0.054 (4) | 0.011 (3) | 0.012 (3) | 0.010 (3) |
C30 | 0.063 (4) | 0.059 (4) | 0.061 (4) | 0.000 (3) | 0.011 (3) | 0.010 (3) |
C31 | 0.062 (4) | 0.071 (5) | 0.064 (4) | 0.005 (4) | −0.006 (3) | −0.003 (4) |
C32 | 0.060 (4) | 0.051 (4) | 0.077 (5) | 0.005 (3) | 0.006 (4) | 0.000 (3) |
C33 | 0.042 (3) | 0.040 (3) | 0.074 (4) | 0.005 (3) | 0.010 (3) | 0.006 (3) |
C34 | 0.037 (3) | 0.051 (4) | 0.059 (4) | 0.011 (3) | 0.008 (3) | 0.007 (3) |
C35 | 0.046 (4) | 0.037 (3) | 0.074 (4) | 0.002 (3) | 0.013 (3) | 0.018 (3) |
C36 | 0.051 (4) | 0.086 (5) | 0.063 (4) | −0.006 (3) | 0.010 (3) | 0.022 (4) |
O3 | 0.036 (2) | 0.081 (3) | 0.087 (3) | 0.014 (2) | 0.014 (2) | 0.005 (2) |
N5 | 0.039 (2) | 0.043 (3) | 0.055 (3) | 0.001 (2) | 0.013 (2) | 0.010 (2) |
N6 | 0.035 (2) | 0.047 (3) | 0.060 (3) | 0.002 (2) | 0.006 (2) | 0.008 (2) |
C37 | 0.040 (3) | 0.046 (3) | 0.042 (3) | −0.001 (3) | 0.011 (2) | 0.008 (2) |
C38 | 0.043 (3) | 0.046 (3) | 0.052 (3) | 0.000 (3) | 0.012 (3) | −0.001 (3) |
C39 | 0.054 (4) | 0.041 (3) | 0.058 (4) | 0.009 (3) | 0.020 (3) | 0.007 (3) |
C40 | 0.043 (3) | 0.053 (4) | 0.052 (3) | 0.013 (3) | 0.021 (3) | 0.014 (3) |
C41 | 0.059 (4) | 0.048 (4) | 0.074 (4) | 0.013 (3) | 0.029 (3) | 0.019 (3) |
C42 | 0.051 (4) | 0.079 (5) | 0.072 (4) | 0.016 (4) | 0.012 (3) | 0.035 (4) |
C43 | 0.043 (3) | 0.086 (6) | 0.064 (4) | 0.000 (3) | 0.008 (3) | 0.020 (4) |
C44 | 0.043 (3) | 0.053 (4) | 0.068 (4) | 0.005 (3) | 0.009 (3) | 0.014 (3) |
C45 | 0.036 (3) | 0.047 (4) | 0.054 (3) | 0.007 (3) | 0.017 (3) | 0.014 (3) |
C46 | 0.075 (5) | 0.045 (4) | 0.085 (5) | 0.002 (3) | 0.015 (4) | 0.010 (3) |
C47 | 0.041 (3) | 0.046 (3) | 0.050 (3) | −0.001 (3) | 0.009 (3) | 0.015 (3) |
C48 | 0.062 (4) | 0.056 (4) | 0.055 (4) | −0.001 (3) | 0.010 (3) | 0.015 (3) |
C49 | 0.060 (4) | 0.081 (5) | 0.059 (4) | −0.015 (4) | −0.010 (3) | 0.028 (4) |
C50 | 0.052 (4) | 0.064 (5) | 0.075 (4) | −0.002 (3) | 0.001 (3) | 0.038 (4) |
C51 | 0.047 (3) | 0.055 (4) | 0.065 (4) | 0.002 (3) | 0.007 (3) | 0.030 (3) |
C52 | 0.042 (3) | 0.040 (3) | 0.054 (3) | −0.006 (3) | 0.011 (3) | 0.012 (3) |
C53 | 0.047 (4) | 0.040 (3) | 0.063 (4) | −0.001 (3) | 0.015 (3) | 0.009 (3) |
C54 | 0.054 (4) | 0.088 (5) | 0.061 (4) | 0.013 (4) | 0.011 (3) | −0.004 (4) |
O4 | 0.037 (2) | 0.096 (4) | 0.085 (3) | −0.015 (2) | 0.013 (2) | 0.011 (3) |
N7 | 0.040 (2) | 0.039 (3) | 0.054 (3) | 0.001 (2) | 0.007 (2) | 0.010 (2) |
N8 | 0.041 (2) | 0.042 (3) | 0.059 (3) | −0.003 (2) | 0.014 (2) | 0.007 (2) |
C55 | 0.042 (3) | 0.047 (3) | 0.045 (3) | 0.003 (3) | 0.007 (3) | 0.008 (3) |
C56 | 0.045 (3) | 0.046 (4) | 0.057 (4) | −0.005 (3) | 0.011 (3) | 0.008 (3) |
C57 | 0.046 (3) | 0.043 (3) | 0.066 (4) | −0.008 (3) | 0.001 (3) | 0.009 (3) |
C58 | 0.032 (3) | 0.049 (4) | 0.048 (3) | −0.010 (2) | −0.005 (2) | 0.010 (3) |
C59 | 0.049 (3) | 0.053 (4) | 0.076 (4) | −0.018 (3) | −0.003 (3) | 0.022 (3) |
C60 | 0.052 (4) | 0.065 (5) | 0.066 (4) | −0.013 (3) | 0.006 (3) | 0.026 (3) |
C61 | 0.040 (3) | 0.085 (5) | 0.061 (4) | 0.002 (3) | 0.014 (3) | 0.022 (4) |
C62 | 0.045 (3) | 0.061 (4) | 0.062 (4) | 0.004 (3) | 0.007 (3) | 0.014 (3) |
C63 | 0.032 (3) | 0.045 (4) | 0.056 (3) | −0.004 (3) | 0.000 (3) | 0.013 (3) |
C64 | 0.059 (4) | 0.051 (4) | 0.097 (5) | −0.010 (3) | 0.014 (4) | 0.012 (4) |
C65 | 0.038 (3) | 0.041 (3) | 0.047 (3) | −0.003 (2) | 0.008 (2) | 0.009 (3) |
C66 | 0.058 (4) | 0.056 (4) | 0.060 (4) | −0.002 (3) | 0.014 (3) | 0.011 (3) |
C67 | 0.066 (4) | 0.083 (5) | 0.052 (4) | 0.016 (4) | 0.021 (3) | 0.027 (4) |
C68 | 0.059 (4) | 0.064 (5) | 0.074 (4) | 0.009 (3) | 0.023 (3) | 0.033 (4) |
C69 | 0.049 (3) | 0.040 (3) | 0.075 (4) | 0.003 (3) | 0.016 (3) | 0.021 (3) |
C70 | 0.041 (3) | 0.041 (3) | 0.058 (4) | 0.003 (3) | 0.007 (3) | 0.015 (3) |
C71 | 0.040 (3) | 0.046 (4) | 0.062 (4) | 0.000 (3) | 0.006 (3) | 0.008 (3) |
C72 | 0.047 (4) | 0.076 (5) | 0.074 (4) | −0.007 (3) | 0.010 (3) | 0.003 (3) |
O1—C17 | 1.220 (7) | C25—H25 | 0.9300 |
O2—C35 | 1.207 (7) | C26—H26 | 0.9300 |
O3—C53 | 1.231 (7) | C28—H28A | 0.9600 |
O4—C71 | 1.233 (7) | C28—H28B | 0.9600 |
N1—C9 | 1.388 (8) | C28—H28C | 0.9600 |
N1—C1 | 1.325 (7) | C30—H30 | 0.9300 |
N2—C17 | 1.353 (8) | C31—H31 | 0.9300 |
N2—C16 | 1.402 (7) | C32—H32 | 0.9300 |
N2—H2N | 0.8600 | C33—H33 | 0.9300 |
N3—C19 | 1.306 (8) | C36—H36B | 0.9600 |
N3—C27 | 1.387 (7) | C36—H36A | 0.9600 |
N4—C35 | 1.356 (8) | C36—H36C | 0.9600 |
N4—C34 | 1.413 (7) | C37—C47 | 1.482 (8) |
N4—H4N | 0.8600 | C37—C38 | 1.419 (8) |
N5—C45 | 1.383 (7) | C38—C39 | 1.363 (8) |
N5—C37 | 1.327 (6) | C39—C46 | 1.497 (9) |
N6—C53 | 1.341 (8) | C39—C40 | 1.425 (8) |
N6—C52 | 1.407 (7) | C40—C45 | 1.404 (9) |
N6—H6N | 0.8600 | C40—C41 | 1.413 (9) |
N7—C63 | 1.384 (8) | C41—C42 | 1.390 (10) |
N7—C55 | 1.331 (7) | C42—C43 | 1.371 (11) |
N8—C71 | 1.349 (8) | C43—C44 | 1.359 (9) |
N8—C70 | 1.398 (7) | C44—C45 | 1.391 (8) |
N8—H8N | 0.8600 | C47—C48 | 1.387 (8) |
C1—C11 | 1.472 (8) | C47—C52 | 1.421 (8) |
C1—C2 | 1.429 (9) | C48—C49 | 1.366 (10) |
C2—C3 | 1.365 (8) | C49—C50 | 1.387 (10) |
C3—C10 | 1.499 (9) | C50—C51 | 1.365 (9) |
C3—C4 | 1.428 (8) | C51—C52 | 1.384 (8) |
C4—C5 | 1.431 (9) | C53—C54 | 1.478 (9) |
C4—C9 | 1.394 (9) | C38—H38 | 0.9300 |
C5—C6 | 1.366 (9) | C41—H41 | 0.9300 |
C6—C7 | 1.405 (10) | C42—H42 | 0.9300 |
C7—C8 | 1.339 (9) | C43—H43 | 0.9300 |
C8—C9 | 1.396 (8) | C44—H44 | 0.9300 |
C11—C12 | 1.403 (8) | C46—H46B | 0.9600 |
C11—C16 | 1.419 (8) | C46—H46A | 0.9600 |
C12—C13 | 1.373 (10) | C46—H46C | 0.9600 |
C13—C14 | 1.385 (10) | C48—H48 | 0.9300 |
C14—C15 | 1.369 (9) | C49—H49 | 0.9300 |
C15—C16 | 1.385 (8) | C50—H50 | 0.9300 |
C17—C18 | 1.482 (8) | C51—H51 | 0.9300 |
C2—H2 | 0.9300 | C54—H54B | 0.9600 |
C5—H5 | 0.9300 | C54—H54A | 0.9600 |
C6—H6 | 0.9300 | C54—H54C | 0.9600 |
C7—H7 | 0.9300 | C55—C65 | 1.486 (8) |
C8—H8 | 0.9300 | C55—C56 | 1.419 (8) |
C10—H10A | 0.9600 | C56—C57 | 1.360 (8) |
C10—H10C | 0.9600 | C57—C64 | 1.491 (9) |
C10—H10B | 0.9600 | C57—C58 | 1.424 (8) |
C12—H12 | 0.9300 | C58—C63 | 1.411 (9) |
C13—H13 | 0.9300 | C58—C59 | 1.416 (9) |
C14—H14 | 0.9300 | C59—C60 | 1.352 (9) |
C15—H15 | 0.9300 | C60—C61 | 1.391 (11) |
C18—H18A | 0.9600 | C61—C62 | 1.375 (9) |
C18—H18B | 0.9600 | C62—C63 | 1.388 (8) |
C18—H18C | 0.9600 | C65—C70 | 1.413 (8) |
C19—C20 | 1.430 (9) | C65—C66 | 1.397 (7) |
C19—C29 | 1.491 (8) | C66—C67 | 1.388 (10) |
C20—C21 | 1.373 (8) | C67—C68 | 1.377 (10) |
C21—C22 | 1.438 (8) | C68—C69 | 1.365 (9) |
C21—C28 | 1.490 (9) | C69—C70 | 1.393 (8) |
C22—C23 | 1.422 (9) | C71—C72 | 1.472 (9) |
C22—C27 | 1.400 (8) | C56—H56 | 0.9300 |
C23—C24 | 1.360 (9) | C59—H59 | 0.9300 |
C24—C25 | 1.396 (10) | C60—H60 | 0.9300 |
C25—C26 | 1.358 (9) | C61—H61 | 0.9300 |
C26—C27 | 1.394 (8) | C62—H62 | 0.9300 |
C29—C34 | 1.407 (8) | C64—H64A | 0.9600 |
C29—C30 | 1.386 (8) | C64—H64B | 0.9600 |
C30—C31 | 1.380 (10) | C64—H64C | 0.9600 |
C31—C32 | 1.386 (11) | C66—H66 | 0.9300 |
C32—C33 | 1.362 (9) | C67—H67 | 0.9300 |
C33—C34 | 1.409 (8) | C68—H68 | 0.9300 |
C35—C36 | 1.481 (8) | C69—H69 | 0.9300 |
C20—H20 | 0.9300 | C72—H72A | 0.9600 |
C23—H23 | 0.9300 | C72—H72B | 0.9600 |
C24—H24 | 0.9300 | C72—H72C | 0.9600 |
O1···N8 | 3.239 (6) | C59···H64B | 2.8400 |
O1···C15 | 2.905 (7) | C59···H64C | 3.0700 |
O1···C72 | 3.236 (8) | C61···H43xii | 2.9100 |
O2···N6i | 3.262 (6) | C64···H59 | 2.7000 |
O2···C33 | 2.894 (7) | C66···H56 | 2.6600 |
O2···C54i | 3.213 (8) | C66···H10Av | 3.1000 |
O3···C51 | 2.927 (7) | C67···H20 | 2.9600 |
O3···C36ii | 3.201 (7) | C67···H28A | 3.0700 |
O3···N4ii | 3.160 (6) | C67···H10Av | 2.8500 |
O4···C18iii | 3.193 (7) | C68···H30 | 2.9500 |
O4···N2iii | 3.181 (6) | C68···H10Av | 2.8400 |
O4···C69 | 2.911 (7) | C69···H10Av | 3.0800 |
O1···H8N | 2.4900 | C71···H69 | 2.8200 |
O1···H15 | 2.5100 | C71···H8iii | 2.9400 |
O1···H72B | 2.6100 | C71···H5v | 2.9200 |
O1···H62 | 2.6100 | C72···H36Axiii | 3.0000 |
O1···H59iv | 2.8200 | H2···C12 | 2.6500 |
O2···H54Bi | 2.2800 | H2···H12 | 2.2100 |
O2···H33 | 2.5100 | H2···C49iv | 2.9400 |
O2···H44i | 2.6000 | H2···H10C | 2.4400 |
O2···H6Ni | 2.5100 | H2N···O4vi | 2.4200 |
O2···H41iii | 2.8300 | H2N···C1 | 2.7900 |
O3···H51 | 2.5300 | H2N···N1 | 2.2500 |
O3···H26ii | 2.6100 | H2N···H18B | 2.3700 |
O3···H4Nii | 2.3900 | H4N···H36B | 2.0900 |
O3···H36Bii | 2.3100 | H4N···C19 | 2.7900 |
O3···H23 | 2.8400 | H4N···O3iv | 2.3900 |
O4···H8iii | 2.6200 | H4N···N3 | 2.2500 |
O4···H5v | 2.8200 | H5···C71viii | 2.9200 |
O4···H69 | 2.5200 | H5···H10B | 2.0800 |
O4···H2Niii | 2.4200 | H5···C10 | 2.6700 |
O4···H18Ciii | 2.7800 | H5···O4viii | 2.8200 |
O4···H18Biii | 2.8800 | H6N···C37 | 2.7800 |
N1···N2 | 2.741 (7) | H6N···O2vii | 2.5100 |
N2···O4vi | 3.181 (6) | H6N···N5 | 2.2100 |
N2···N1 | 2.741 (7) | H6N···H54B | 2.1600 |
N3···N4 | 2.735 (7) | H8···O4vi | 2.6200 |
N4···O3iv | 3.160 (6) | H8···C71vi | 2.9400 |
N4···N3 | 2.735 (7) | H8N···O1 | 2.4900 |
N5···N6 | 2.703 (7) | H8N···N7 | 2.2000 |
N6···O2vii | 3.262 (6) | H8N···H72B | 2.1700 |
N6···N5 | 2.703 (7) | H8N···C55 | 2.7700 |
N7···N8 | 2.705 (7) | H10A···C69viii | 3.0800 |
N8···O1 | 3.239 (6) | H10A···C66viii | 3.1000 |
N8···N7 | 2.705 (7) | H10A···C67viii | 2.8500 |
N1···H2N | 2.2500 | H10A···C68viii | 2.8400 |
N3···H4N | 2.2500 | H10B···C5 | 2.6100 |
N5···H6N | 2.2100 | H10B···H5 | 2.0800 |
N7···H8N | 2.2000 | H10C···H2 | 2.4400 |
C1···C59iv | 3.474 (8) | H12···C50iv | 2.9100 |
C2···C59iv | 3.548 (9) | H12···H2 | 2.2100 |
C3···C61iv | 3.524 (8) | H12···C2 | 2.6700 |
C4···C61iv | 3.590 (8) | H13···C19 | 3.0900 |
C4···C56viii | 3.592 (8) | H13···H46A | 2.5900 |
C5···C56viii | 3.586 (8) | H15···C17 | 2.7900 |
C5···C55viii | 3.486 (8) | H15···O1 | 2.5100 |
C7···C57viii | 3.550 (9) | H18B···C54ix | 3.0800 |
C8···C64viii | 3.525 (9) | H18B···H2N | 2.3700 |
C8···C57viii | 3.599 (8) | H18B···H54Aix | 2.3300 |
C10···C62iv | 3.525 (9) | H18B···O4vi | 2.8800 |
C12···C50iv | 3.575 (9) | H18C···O4vi | 2.7800 |
C15···O1 | 2.905 (7) | H20···H30 | 2.2500 |
C18···O4vi | 3.193 (7) | H20···C30 | 2.6600 |
C19···C41iii | 3.480 (9) | H20···H28A | 2.3500 |
C20···C40iii | 3.597 (8) | H20···C67 | 2.9600 |
C20···C41iii | 3.525 (9) | H23···O3 | 2.8400 |
C21···C43iii | 3.563 (8) | H23···H28C | 2.3000 |
C22···C38 | 3.594 (8) | H23···C28 | 2.6700 |
C23···C38 | 3.578 (9) | H23···C53 | 2.9000 |
C23···C37 | 3.470 (8) | H26···H54Aiv | 2.5800 |
C25···C40 | 3.589 (8) | H26···O3iv | 2.6100 |
C25···C39 | 3.572 (8) | H26···C53iv | 2.9500 |
C26···C46 | 3.559 (9) | H28A···C67 | 3.0700 |
C28···C44iii | 3.550 (9) | H28A···H20 | 2.3500 |
C33···O2 | 2.894 (7) | H28B···C52 | 3.0400 |
C36···O3iv | 3.201 (7) | H28B···C23 | 3.0900 |
C37···C23 | 3.470 (8) | H28B···C48 | 3.0600 |
C38···C23 | 3.578 (9) | H28B···C49 | 2.9000 |
C38···C22 | 3.594 (8) | H28B···C50 | 2.8000 |
C39···C25 | 3.572 (8) | H28B···C51 | 2.8800 |
C40···C20vi | 3.597 (8) | H28C···H23 | 2.3000 |
C40···C25 | 3.589 (8) | H28C···C44iii | 3.0900 |
C41···C20vi | 3.525 (9) | H28C···C23 | 2.7800 |
C41···C19vi | 3.480 (9) | H30···C68 | 2.9500 |
C43···C21vi | 3.563 (8) | H30···H20 | 2.2500 |
C44···C28vi | 3.550 (9) | H30···C20 | 2.6800 |
C46···C26 | 3.559 (9) | H31···H64Aiv | 2.5700 |
C50···C12ii | 3.575 (9) | H33···C35 | 2.8000 |
C51···O3 | 2.927 (7) | H33···O2 | 2.5100 |
C54···O2vii | 3.213 (8) | H36A···H72Ax | 2.4100 |
C55···C5v | 3.486 (8) | H36A···C72x | 3.0000 |
C56···C5v | 3.586 (8) | H36B···O3iv | 2.3100 |
C56···C4v | 3.592 (8) | H36B···H4N | 2.0900 |
C57···C7v | 3.550 (9) | H36C···H44i | 2.4800 |
C57···C8v | 3.599 (8) | H38···H46A | 2.3100 |
C59···C2ii | 3.548 (9) | H38···H48 | 2.2700 |
C59···C1ii | 3.474 (8) | H38···C13 | 2.9600 |
C61···C4ii | 3.590 (8) | H38···C48 | 2.6900 |
C61···C3ii | 3.524 (8) | H41···C46 | 2.6700 |
C62···C10ii | 3.525 (9) | H41···O2vi | 2.8300 |
C64···C8v | 3.525 (9) | H41···C35vi | 2.9700 |
C69···O4 | 2.911 (7) | H41···H46C | 2.4100 |
C72···O1 | 3.236 (8) | H41···H46B | 2.5500 |
C1···H2N | 2.7900 | H43···C61xiv | 2.9100 |
C2···H12 | 2.6700 | H44···O2vii | 2.6000 |
C5···H10B | 2.6100 | H44···C35vii | 2.8900 |
C7···H54Cix | 3.0300 | H44···H36Cvii | 2.4800 |
C8···H64Bviii | 3.0200 | H46A···C12 | 3.0400 |
C8···H54Cix | 2.9600 | H46A···C13 | 2.9500 |
C10···H5 | 2.6700 | H46A···H38 | 2.3100 |
C12···H46A | 3.0400 | H46A···H13 | 2.5900 |
C12···H64Civ | 3.0700 | H46B···C26 | 2.8900 |
C12···H2 | 2.6500 | H46B···C41 | 2.9800 |
C13···H38 | 2.9600 | H46B···H41 | 2.5500 |
C13···H46A | 2.9500 | H46C···C31vi | 3.0200 |
C13···H64Civ | 2.9100 | H46C···C32vi | 2.8700 |
C14···H48 | 2.9300 | H46C···H41 | 2.4100 |
C14···H64Civ | 2.8100 | H46C···C41 | 2.8800 |
C15···H64Civ | 2.9000 | H46C···C34vi | 2.9800 |
C16···H64Civ | 3.0800 | H46C···C33vi | 2.8500 |
C17···H62 | 2.8900 | H48···H38 | 2.2700 |
C17···H15 | 2.7900 | H48···C38 | 2.7100 |
C17···H59iv | 2.9700 | H48···C14 | 2.9300 |
C18···H62 | 3.0800 | H49···C55 | 3.0500 |
C18···H54Aix | 3.0900 | H51···O3 | 2.5300 |
C19···H13 | 3.0900 | H51···C53 | 2.8200 |
C19···H4N | 2.7900 | H54A···H26ii | 2.5800 |
C20···H30 | 2.6800 | H54A···C18xi | 3.0900 |
C23···H28C | 2.7800 | H54A···H18Bxi | 2.3300 |
C23···H28B | 3.0900 | H54B···O2vii | 2.2800 |
C24···H61x | 2.9200 | H54B···H6N | 2.1600 |
C26···H46B | 2.8900 | H54C···C7xi | 3.0300 |
C28···H23 | 2.6700 | H54C···C8xi | 2.9600 |
C30···H20 | 2.6600 | H56···C31ii | 2.9600 |
C31···H64Aiv | 3.0100 | H56···C66 | 2.6600 |
C31···H46Ciii | 3.0200 | H56···H64A | 2.3200 |
C31···H56iv | 2.9600 | H56···H66 | 2.2300 |
C32···H66iv | 2.9200 | H59···O1ii | 2.8200 |
C32···H46Ciii | 2.8700 | H59···C17ii | 2.9700 |
C33···H46Ciii | 2.8500 | H59···C64 | 2.7000 |
C34···H46Ciii | 2.9800 | H59···H64B | 2.3800 |
C35···H33 | 2.8000 | H61···C24xiii | 2.9200 |
C35···H41iii | 2.9700 | H62···O1 | 2.6100 |
C35···H44i | 2.8900 | H62···C17 | 2.8900 |
C37···H6N | 2.7800 | H62···C18 | 3.0800 |
C37···H67vi | 3.0600 | H64A···C31ii | 3.0100 |
C38···H48 | 2.7100 | H64A···H31ii | 2.5700 |
C41···H46B | 2.9800 | H64A···H56 | 2.3200 |
C41···H46C | 2.8800 | H64B···C8v | 3.0200 |
C44···H28Cvi | 3.0900 | H64B···C59 | 2.8400 |
C46···H41 | 2.6700 | H64B···H59 | 2.3800 |
C48···H28B | 3.0600 | H64C···C12ii | 3.0700 |
C48···H38 | 2.6900 | H64C···C13ii | 2.9100 |
C49···H2ii | 2.9400 | H64C···C14ii | 2.8100 |
C49···H28B | 2.9000 | H64C···C15ii | 2.9000 |
C50···H12ii | 2.9100 | H64C···C16ii | 3.0800 |
C50···H28B | 2.8000 | H64C···C59 | 3.0700 |
C51···H28B | 2.8800 | H66···C32ii | 2.9200 |
C52···H28B | 3.0400 | H66···C56 | 2.6800 |
C53···H26ii | 2.9500 | H66···H56 | 2.2300 |
C53···H23 | 2.9000 | H67···C37iii | 3.0600 |
C53···H51 | 2.8200 | H69···O4 | 2.5200 |
C54···H18Bxi | 3.0800 | H69···C71 | 2.8200 |
C55···H49 | 3.0500 | H72A···H36Axiii | 2.4100 |
C55···H8N | 2.7700 | H72B···O1 | 2.6100 |
C56···H66 | 2.6800 | H72B···H8N | 2.1700 |
C1—N1—C9 | 118.3 (5) | C32—C33—H33 | 120.00 |
C16—N2—C17 | 125.6 (5) | C34—C33—H33 | 120.00 |
C17—N2—H2N | 117.00 | H36B—C36—H36C | 110.00 |
C16—N2—H2N | 117.00 | C35—C36—H36B | 109.00 |
C19—N3—C27 | 118.8 (5) | C35—C36—H36A | 109.00 |
C34—N4—C35 | 125.4 (5) | H36A—C36—H36C | 109.00 |
C34—N4—H4N | 117.00 | C35—C36—H36C | 109.00 |
C35—N4—H4N | 117.00 | H36A—C36—H36B | 109.00 |
C37—N5—C45 | 117.9 (5) | N5—C37—C38 | 121.5 (5) |
C52—N6—C53 | 126.3 (5) | N5—C37—C47 | 118.3 (5) |
C53—N6—H6N | 117.00 | C38—C37—C47 | 120.1 (5) |
C52—N6—H6N | 117.00 | C37—C38—C39 | 121.6 (5) |
C55—N7—C63 | 117.2 (5) | C38—C39—C46 | 120.7 (6) |
C70—N8—C71 | 126.7 (5) | C40—C39—C46 | 121.2 (5) |
C71—N8—H8N | 117.00 | C38—C39—C40 | 118.0 (6) |
C70—N8—H8N | 117.00 | C39—C40—C41 | 123.3 (6) |
N1—C1—C2 | 121.3 (5) | C41—C40—C45 | 119.2 (5) |
N1—C1—C11 | 119.1 (5) | C39—C40—C45 | 117.5 (5) |
C2—C1—C11 | 119.6 (5) | C40—C41—C42 | 119.4 (6) |
C1—C2—C3 | 121.3 (5) | C41—C42—C43 | 120.2 (7) |
C4—C3—C10 | 121.3 (5) | C42—C43—C44 | 121.1 (6) |
C2—C3—C4 | 117.9 (5) | C43—C44—C45 | 120.9 (6) |
C2—C3—C10 | 120.8 (5) | N5—C45—C40 | 123.4 (5) |
C3—C4—C9 | 118.2 (5) | N5—C45—C44 | 117.3 (5) |
C5—C4—C9 | 118.7 (5) | C40—C45—C44 | 119.2 (6) |
C3—C4—C5 | 123.1 (6) | C48—C47—C52 | 116.7 (6) |
C4—C5—C6 | 119.7 (6) | C37—C47—C48 | 120.4 (5) |
C5—C6—C7 | 119.9 (6) | C37—C47—C52 | 122.8 (5) |
C6—C7—C8 | 121.1 (6) | C47—C48—C49 | 123.0 (6) |
C7—C8—C9 | 120.8 (6) | C48—C49—C50 | 118.9 (6) |
C4—C9—C8 | 119.8 (5) | C49—C50—C51 | 120.6 (6) |
N1—C9—C8 | 117.2 (5) | C50—C51—C52 | 120.4 (6) |
N1—C9—C4 | 123.0 (5) | N6—C52—C47 | 119.5 (5) |
C1—C11—C12 | 119.5 (5) | N6—C52—C51 | 120.2 (5) |
C1—C11—C16 | 123.6 (5) | C47—C52—C51 | 120.3 (5) |
C12—C11—C16 | 116.9 (5) | N6—C53—C54 | 116.1 (5) |
C11—C12—C13 | 122.2 (6) | O3—C53—C54 | 120.3 (6) |
C12—C13—C14 | 119.4 (6) | O3—C53—N6 | 123.6 (5) |
C13—C14—C15 | 120.5 (6) | C37—C38—H38 | 119.00 |
C14—C15—C16 | 120.7 (6) | C39—C38—H38 | 119.00 |
N2—C16—C15 | 120.0 (5) | C40—C41—H41 | 120.00 |
N2—C16—C11 | 119.7 (5) | C42—C41—H41 | 120.00 |
C11—C16—C15 | 120.3 (5) | C43—C42—H42 | 120.00 |
O1—C17—C18 | 120.7 (5) | C41—C42—H42 | 120.00 |
O1—C17—N2 | 122.8 (5) | C42—C43—H43 | 119.00 |
N2—C17—C18 | 116.5 (5) | C44—C43—H43 | 119.00 |
C3—C2—H2 | 119.00 | C43—C44—H44 | 120.00 |
C1—C2—H2 | 119.00 | C45—C44—H44 | 120.00 |
C4—C5—H5 | 120.00 | H46A—C46—H46C | 109.00 |
C6—C5—H5 | 120.00 | C39—C46—H46C | 109.00 |
C7—C6—H6 | 120.00 | H46A—C46—H46B | 109.00 |
C5—C6—H6 | 120.00 | C39—C46—H46A | 109.00 |
C6—C7—H7 | 119.00 | C39—C46—H46B | 109.00 |
C8—C7—H7 | 119.00 | H46B—C46—H46C | 110.00 |
C9—C8—H8 | 120.00 | C49—C48—H48 | 119.00 |
C7—C8—H8 | 120.00 | C47—C48—H48 | 119.00 |
C3—C10—H10A | 109.00 | C48—C49—H49 | 121.00 |
H10B—C10—H10C | 109.00 | C50—C49—H49 | 120.00 |
H10A—C10—H10B | 110.00 | C51—C50—H50 | 120.00 |
C3—C10—H10B | 110.00 | C49—C50—H50 | 120.00 |
C3—C10—H10C | 109.00 | C50—C51—H51 | 120.00 |
H10A—C10—H10C | 109.00 | C52—C51—H51 | 120.00 |
C11—C12—H12 | 119.00 | H54A—C54—H54C | 110.00 |
C13—C12—H12 | 119.00 | H54B—C54—H54C | 109.00 |
C14—C13—H13 | 120.00 | H54A—C54—H54B | 109.00 |
C12—C13—H13 | 120.00 | C53—C54—H54A | 109.00 |
C15—C14—H14 | 120.00 | C53—C54—H54B | 109.00 |
C13—C14—H14 | 120.00 | C53—C54—H54C | 110.00 |
C16—C15—H15 | 120.00 | C56—C55—C65 | 119.8 (5) |
C14—C15—H15 | 120.00 | N7—C55—C56 | 122.2 (5) |
C17—C18—H18B | 110.00 | N7—C55—C65 | 117.9 (5) |
C17—C18—H18A | 110.00 | C55—C56—C57 | 121.4 (5) |
H18A—C18—H18B | 109.00 | C56—C57—C58 | 118.1 (6) |
H18A—C18—H18C | 109.00 | C56—C57—C64 | 120.9 (6) |
C17—C18—H18C | 110.00 | C58—C57—C64 | 121.0 (6) |
H18B—C18—H18C | 109.00 | C57—C58—C59 | 124.9 (6) |
N3—C19—C20 | 122.3 (5) | C59—C58—C63 | 117.4 (5) |
N3—C19—C29 | 119.1 (5) | C57—C58—C63 | 117.7 (5) |
C20—C19—C29 | 118.5 (5) | C58—C59—C60 | 121.4 (6) |
C19—C20—C21 | 120.7 (5) | C59—C60—C61 | 120.9 (6) |
C20—C21—C22 | 117.5 (5) | C60—C61—C62 | 119.1 (6) |
C20—C21—C28 | 121.4 (6) | C61—C62—C63 | 121.2 (6) |
C22—C21—C28 | 121.2 (5) | N7—C63—C58 | 123.4 (5) |
C21—C22—C23 | 123.0 (6) | C58—C63—C62 | 119.9 (5) |
C21—C22—C27 | 118.4 (5) | N7—C63—C62 | 116.7 (6) |
C23—C22—C27 | 118.5 (5) | C55—C65—C70 | 122.9 (4) |
C22—C23—C24 | 120.0 (6) | C66—C65—C70 | 117.8 (5) |
C23—C24—C25 | 120.3 (6) | C55—C65—C66 | 119.3 (5) |
C24—C25—C26 | 120.9 (6) | C65—C66—C67 | 121.3 (6) |
C25—C26—C27 | 120.0 (6) | C66—C67—C68 | 119.5 (6) |
N3—C27—C22 | 122.4 (5) | C67—C68—C69 | 120.9 (6) |
N3—C27—C26 | 117.4 (5) | C68—C69—C70 | 120.6 (6) |
C22—C27—C26 | 120.2 (5) | N8—C70—C69 | 120.3 (5) |
C30—C29—C34 | 117.5 (6) | C65—C70—C69 | 119.9 (5) |
C19—C29—C34 | 122.4 (5) | N8—C70—C65 | 119.7 (5) |
C19—C29—C30 | 120.0 (6) | N8—C71—C72 | 116.4 (5) |
C29—C30—C31 | 122.6 (6) | O4—C71—N8 | 122.1 (5) |
C30—C31—C32 | 118.4 (7) | O4—C71—C72 | 121.5 (6) |
C31—C32—C33 | 121.6 (6) | C55—C56—H56 | 119.00 |
C32—C33—C34 | 119.6 (6) | C57—C56—H56 | 119.00 |
N4—C34—C29 | 120.8 (5) | C58—C59—H59 | 119.00 |
N4—C34—C33 | 119.0 (5) | C60—C59—H59 | 119.00 |
C29—C34—C33 | 120.2 (5) | C59—C60—H60 | 120.00 |
N4—C35—C36 | 114.6 (5) | C61—C60—H60 | 119.00 |
O2—C35—N4 | 122.7 (6) | C60—C61—H61 | 120.00 |
O2—C35—C36 | 122.7 (6) | C62—C61—H61 | 120.00 |
C21—C20—H20 | 120.00 | C61—C62—H62 | 119.00 |
C19—C20—H20 | 120.00 | C63—C62—H62 | 119.00 |
C22—C23—H23 | 120.00 | C57—C64—H64A | 109.00 |
C24—C23—H23 | 120.00 | C57—C64—H64B | 109.00 |
C25—C24—H24 | 120.00 | C57—C64—H64C | 109.00 |
C23—C24—H24 | 120.00 | H64A—C64—H64B | 109.00 |
C26—C25—H25 | 120.00 | H64A—C64—H64C | 110.00 |
C24—C25—H25 | 120.00 | H64B—C64—H64C | 109.00 |
C25—C26—H26 | 120.00 | C65—C66—H66 | 119.00 |
C27—C26—H26 | 120.00 | C67—C66—H66 | 119.00 |
H28A—C28—H28C | 109.00 | C66—C67—H67 | 120.00 |
C21—C28—H28A | 109.00 | C68—C67—H67 | 120.00 |
H28A—C28—H28B | 109.00 | C67—C68—H68 | 120.00 |
C21—C28—H28B | 109.00 | C69—C68—H68 | 120.00 |
H28B—C28—H28C | 109.00 | C68—C69—H69 | 120.00 |
C21—C28—H28C | 110.00 | C70—C69—H69 | 120.00 |
C29—C30—H30 | 119.00 | C71—C72—H72A | 109.00 |
C31—C30—H30 | 119.00 | C71—C72—H72B | 109.00 |
C32—C31—H31 | 121.00 | C71—C72—H72C | 109.00 |
C30—C31—H31 | 121.00 | H72A—C72—H72B | 110.00 |
C33—C32—H32 | 119.00 | H72A—C72—H72C | 110.00 |
C31—C32—H32 | 119.00 | H72B—C72—H72C | 109.00 |
C9—N1—C1—C2 | 2.3 (8) | C22—C23—C24—C25 | −1.8 (9) |
C9—N1—C1—C11 | −173.9 (5) | C23—C24—C25—C26 | 0.9 (10) |
C1—N1—C9—C4 | −2.0 (8) | C24—C25—C26—C27 | 0.9 (9) |
C1—N1—C9—C8 | 177.4 (5) | C25—C26—C27—N3 | −179.1 (5) |
C17—N2—C16—C11 | 136.2 (6) | C25—C26—C27—C22 | −1.9 (9) |
C17—N2—C16—C15 | −42.2 (8) | C30—C29—C34—N4 | 178.0 (5) |
C16—N2—C17—O1 | −2.1 (10) | C34—C29—C30—C31 | 3.1 (10) |
C16—N2—C17—C18 | −179.7 (6) | C19—C29—C34—N4 | −6.1 (9) |
C27—N3—C19—C20 | −0.4 (8) | C30—C29—C34—C33 | −2.7 (8) |
C27—N3—C19—C29 | −175.4 (5) | C19—C29—C34—C33 | 173.2 (5) |
C19—N3—C27—C22 | 0.2 (8) | C19—C29—C30—C31 | −172.9 (6) |
C19—N3—C27—C26 | 177.4 (5) | C29—C30—C31—C32 | −1.9 (11) |
C35—N4—C34—C33 | −42.6 (8) | C30—C31—C32—C33 | 0.2 (11) |
C34—N4—C35—O2 | −1.0 (10) | C31—C32—C33—C34 | 0.2 (10) |
C35—N4—C34—C29 | 136.7 (6) | C32—C33—C34—N4 | −179.6 (6) |
C34—N4—C35—C36 | −179.7 (6) | C32—C33—C34—C29 | 1.1 (9) |
C37—N5—C45—C44 | −176.9 (5) | C47—C37—C38—C39 | −176.5 (5) |
C37—N5—C45—C40 | 1.9 (8) | N5—C37—C47—C48 | 151.7 (6) |
C45—N5—C37—C47 | 174.4 (5) | N5—C37—C38—C39 | −0.3 (8) |
C45—N5—C37—C38 | −1.9 (7) | C38—C37—C47—C52 | 145.0 (6) |
C53—N6—C52—C47 | −135.1 (6) | N5—C37—C47—C52 | −31.3 (8) |
C52—N6—C53—O3 | −3.6 (10) | C38—C37—C47—C48 | −32.0 (8) |
C53—N6—C52—C51 | 43.5 (9) | C37—C38—C39—C40 | 2.4 (9) |
C52—N6—C53—C54 | 174.8 (6) | C37—C38—C39—C46 | 178.2 (5) |
C55—N7—C63—C58 | 1.6 (8) | C46—C39—C40—C45 | −178.1 (6) |
C55—N7—C63—C62 | −177.6 (5) | C38—C39—C40—C41 | 177.8 (6) |
C63—N7—C55—C65 | 174.9 (5) | C38—C39—C40—C45 | −2.3 (8) |
C63—N7—C55—C56 | −1.9 (8) | C46—C39—C40—C41 | 2.1 (9) |
C70—N8—C71—C72 | 175.2 (6) | C45—C40—C41—C42 | 0.4 (9) |
C71—N8—C70—C65 | −135.5 (6) | C39—C40—C45—N5 | 0.2 (8) |
C70—N8—C71—O4 | −1.8 (10) | C39—C40—C45—C44 | 179.0 (5) |
C71—N8—C70—C69 | 42.6 (9) | C41—C40—C45—N5 | −179.9 (5) |
C11—C1—C2—C3 | 174.8 (5) | C41—C40—C45—C44 | −1.1 (8) |
N1—C1—C11—C12 | −152.0 (6) | C39—C40—C41—C42 | −179.8 (6) |
C2—C1—C11—C12 | 31.8 (8) | C40—C41—C42—C43 | 0.7 (10) |
N1—C1—C11—C16 | 31.9 (8) | C41—C42—C43—C44 | −0.9 (10) |
C2—C1—C11—C16 | −144.3 (6) | C42—C43—C44—C45 | 0.1 (9) |
N1—C1—C2—C3 | −1.4 (9) | C43—C44—C45—N5 | 179.8 (5) |
C1—C2—C3—C4 | 0.0 (8) | C43—C44—C45—C40 | 0.9 (9) |
C1—C2—C3—C10 | −178.9 (6) | C37—C47—C48—C49 | 172.9 (6) |
C10—C3—C4—C9 | 179.2 (5) | C52—C47—C48—C49 | −4.2 (10) |
C2—C3—C4—C9 | 0.3 (8) | C37—C47—C52—N6 | 5.1 (8) |
C10—C3—C4—C5 | 1.6 (9) | C48—C47—C52—N6 | −177.8 (5) |
C2—C3—C4—C5 | −177.3 (5) | C48—C47—C52—C51 | 3.6 (8) |
C3—C4—C9—C8 | −178.7 (5) | C37—C47—C52—C51 | −173.5 (5) |
C5—C4—C9—N1 | 178.4 (5) | C47—C48—C49—C50 | 2.3 (11) |
C9—C4—C5—C6 | 0.7 (8) | C48—C49—C50—C51 | 0.4 (10) |
C5—C4—C9—C8 | −1.0 (8) | C49—C50—C51—C52 | −0.9 (10) |
C3—C4—C9—N1 | 0.7 (8) | C50—C51—C52—N6 | −179.8 (6) |
C3—C4—C5—C6 | 178.3 (6) | C50—C51—C52—C47 | −1.2 (9) |
C4—C5—C6—C7 | 0.4 (9) | N7—C55—C56—C57 | 1.0 (9) |
C5—C6—C7—C8 | −1.1 (10) | C65—C55—C56—C57 | −175.7 (5) |
C6—C7—C8—C9 | 0.8 (10) | N7—C55—C65—C66 | 151.4 (5) |
C7—C8—C9—C4 | 0.2 (9) | N7—C55—C65—C70 | −32.0 (7) |
C7—C8—C9—N1 | −179.2 (6) | C56—C55—C65—C66 | −31.7 (7) |
C12—C11—C16—N2 | 178.4 (5) | C56—C55—C65—C70 | 144.9 (5) |
C16—C11—C12—C13 | 2.9 (9) | C55—C56—C57—C58 | 0.3 (9) |
C1—C11—C16—C15 | 173.0 (5) | C55—C56—C57—C64 | 178.5 (6) |
C1—C11—C16—N2 | −5.4 (8) | C56—C57—C58—C59 | 178.5 (6) |
C12—C11—C16—C15 | −3.3 (8) | C56—C57—C58—C63 | −0.7 (8) |
C1—C11—C12—C13 | −173.5 (6) | C64—C57—C58—C59 | 0.3 (9) |
C11—C12—C13—C14 | −1.2 (10) | C64—C57—C58—C63 | −178.9 (5) |
C12—C13—C14—C15 | −0.2 (10) | C57—C58—C59—C60 | −179.1 (6) |
C13—C14—C15—C16 | −0.2 (10) | C63—C58—C59—C60 | 0.0 (9) |
C14—C15—C16—C11 | 2.0 (9) | C57—C58—C63—N7 | −0.3 (8) |
C14—C15—C16—N2 | −179.6 (6) | C57—C58—C63—C62 | 178.9 (5) |
N3—C19—C20—C21 | 1.2 (9) | C59—C58—C63—N7 | −179.5 (5) |
C29—C19—C20—C21 | 176.2 (5) | C59—C58—C63—C62 | −0.3 (8) |
C20—C19—C29—C34 | −142.6 (6) | C58—C59—C60—C61 | 0.2 (10) |
C20—C19—C29—C30 | 33.1 (8) | C59—C60—C61—C62 | 0.0 (9) |
N3—C19—C29—C30 | −151.7 (6) | C60—C61—C62—C63 | −0.3 (9) |
N3—C19—C29—C34 | 32.5 (8) | C61—C62—C63—N7 | 179.7 (5) |
C19—C20—C21—C22 | −1.7 (9) | C61—C62—C63—C58 | 0.5 (9) |
C19—C20—C21—C28 | −179.2 (6) | C55—C65—C66—C67 | 173.5 (6) |
C28—C21—C22—C27 | 179.0 (6) | C70—C65—C66—C67 | −3.3 (9) |
C28—C21—C22—C23 | 0.2 (9) | C55—C65—C70—N8 | 4.7 (8) |
C20—C21—C22—C23 | −177.3 (6) | C55—C65—C70—C69 | −173.5 (5) |
C20—C21—C22—C27 | 1.5 (8) | C66—C65—C70—N8 | −178.7 (5) |
C21—C22—C23—C24 | 179.6 (6) | C66—C65—C70—C69 | 3.2 (8) |
C21—C22—C27—C26 | −177.8 (5) | C65—C66—C67—C68 | 1.4 (10) |
C27—C22—C23—C24 | 0.9 (9) | C66—C67—C68—C69 | 0.7 (10) |
C21—C22—C27—N3 | −0.7 (8) | C67—C68—C69—C70 | −0.8 (10) |
C23—C22—C27—C26 | 1.0 (9) | C68—C69—C70—N8 | −179.4 (6) |
C23—C22—C27—N3 | 178.1 (5) | C68—C69—C70—C65 | −1.2 (9) |
Symmetry codes: (i) x−1, y−1, z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) x, y−1, z; (v) x−1, y+1, z; (vi) x+1, y, z; (vii) x+1, y+1, z; (viii) x+1, y−1, z; (ix) x, y−1, z−1; (x) x, y, z+1; (xi) x, y+1, z+1; (xii) x−1, y, z−1; (xiii) x, y, z−1; (xiv) x+1, y, z+1. |
Cg3, Cg7, Cg11, Cg15 are the centroids of the C11–C16, C29–C34, C47–C52 and C65–C70 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O4vi | 0.86 | 2.42 | 3.181 (6) | 148 |
N2—H2N···N1 | 0.86 | 2.25 | 2.741 (7) | 117 |
N4—H4N···O3iv | 0.86 | 2.39 | 3.160 (6) | 149 |
N4—H4N···N3 | 0.86 | 2.25 | 2.735 (7) | 116 |
N6—H6N···O2vii | 0.86 | 2.51 | 3.262 (6) | 147 |
N6—H6N···N5 | 0.86 | 2.21 | 2.703 (7) | 116 |
N8—H8N···O1 | 0.86 | 2.49 | 3.239 (6) | 146 |
N8—H8N···N7 | 0.86 | 2.20 | 2.705 (7) | 118 |
C15—H15···O1 | 0.93 | 2.51 | 2.905 (7) | 106 |
C33—H33···O2 | 0.93 | 2.51 | 2.894 (7) | 105 |
C36—H36B···O3iv | 0.96 | 2.31 | 3.201 (7) | 154 |
C44—H44···O2vii | 0.93 | 2.60 | 3.472 (9) | 157 |
C51—H51···O3 | 0.93 | 2.53 | 2.927 (7) | 106 |
C54—H54B···O2vii | 0.96 | 2.28 | 3.213 (8) | 162 |
C69—H69···O4 | 0.93 | 2.52 | 2.911 (7) | 106 |
C10—H10A···Cg15viii | 0.96 | 2.76 | 3.586 (7) | 145 |
C28—H28B···Cg11 | 0.96 | 2.63 | 3.579 (7) | 171 |
C46—H46C···Cg7vi | 0.96 | 2.65 | 3.594 (7) | 168 |
C64—H64C···Cg3ii | 0.96 | 2.65 | 3.604 (7) | 173 |
Symmetry codes: (ii) x, y+1, z; (iv) x, y−1, z; (vi) x+1, y, z; (vii) x+1, y+1, z; (viii) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H16N2O |
Mr | 276.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 9.7383 (5), 9.9035 (6), 15.2809 (9) |
α, β, γ (°) | 101.414 (5), 99.188 (5), 90.065 (5) |
V (Å3) | 1425.24 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Oxford Xcalibur Eos(Nova) CCD detector |
Absorption correction | Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.984, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29328, 5290, 3314 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.164, 0.94 |
No. of reflections | 5290 |
No. of parameters | 766 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
Cg3, Cg7, Cg11, Cg15 are the centroids of the C11–C16, C29–C34, C47–C52 and C65–C70 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O4i | 0.86 | 2.42 | 3.181 (6) | 148 |
N2—H2N···N1 | 0.86 | 2.25 | 2.741 (7) | 117 |
N4—H4N···O3ii | 0.86 | 2.39 | 3.160 (6) | 149 |
N4—H4N···N3 | 0.86 | 2.25 | 2.735 (7) | 116 |
N6—H6N···O2iii | 0.86 | 2.51 | 3.262 (6) | 147 |
N6—H6N···N5 | 0.86 | 2.21 | 2.703 (7) | 116 |
N8—H8N···O1 | 0.86 | 2.49 | 3.239 (6) | 146 |
N8—H8N···N7 | 0.86 | 2.20 | 2.705 (7) | 118 |
C36—H36B···O3ii | 0.96 | 2.31 | 3.201 (7) | 154 |
C44—H44···O2iii | 0.93 | 2.60 | 3.472 (9) | 157 |
C54—H54B···O2iii | 0.96 | 2.28 | 3.213 (8) | 162 |
C10—H10A···Cg15iv | 0.96 | 2.76 | 3.586 (7) | 145 |
C28—H28B···Cg11 | 0.96 | 2.63 | 3.579 (7) | 171 |
C46—H46C···Cg7i | 0.96 | 2.65 | 3.594 (7) | 168 |
C64—H64C···Cg3v | 0.96 | 2.65 | 3.604 (7) | 173 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x+1, y+1, z; (iv) x+1, y−1, z; (v) x, y+1, z. |
Acknowledgements
We thank the DDepartment of Science and Technology (DST), India, and Professor T. N. Guru Row, IISc, Bangalore, for use of the CCD facility set up under the IRHPA–DST program at IISc. FNK thanks the DST for Fast Track Proposal funding.
References
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Quinolines and their derivatives occur in numerous natural products, many of which possess interesting physiological and biological properties. Quinoline derivatives have been developed for the treatment of many diseases like malaria, HIV, tumor, and antibacterial infections (Yates, 1984). Since the turn of the century, the development of concise and effective methodologies for the preparation of libraries of small molecules for research in drug discovery has remained a major challenge. A number of strategies have been developed to address this challenge (Roopan et al., 2009, Roopan et al., 2010). We herewith reporting the synthesis of 2-substituted quinoline using 1-(2-aminophenyl)ethanone in acetic acid and drop of sulphuric acid at 453 K.
The title compound crystallizes in the triclinic space group P 1 with four independent molecules, A, B, C and D with O1, O2, O3 and O4, respectively, in the asymmetric unit (Figs. 1-4) with no evidence of pseudo- or non-crystallographic symmetry. Crystals belonging to this class, namely Z' = 4 in space group P 1, are not uncommon (Bernés et al., 2003). The molecules A and B have an irregular -ac, -ac, +ap conformation (C2-C1-C11-C16, C11-C16-N2-C17, C16-N2-C17-C18 in molecule A and C20-C19-C29-C34, C29-C34-N4-C35, C34-N4-C35-C36 in molecule B) while the other molecules C and D exhibit a different, +ac, +ac, +ap conformation (C38-C37-C47-C52, C47-C52-N6-C53, C52-N6-C53-C54 in molecule C and C56-C55-C65-C70, C65-C70-N8-C71, C70-N8-C71-C72 in molecule D). The planar quinoline ring system of each molecule makes a dihedral angle of 32.8 (2)° for A, 33.4 (2)° for B, 31.7 (2)° for C and 32.3 (2)° for D with the benzene ring [C11–C16 for A, C29–C34 for B, C47–C52 for C and C65–C70 for D] bound to it.
The crystal packing is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 5), and are further consolidated by C—H···π (Table 1) and π-π stacking interactions [Cg1···Cg14(x, -1 + y, z) = 3.728 (3), Cg2···Cg13 (1 + x, -1 + y, z) = 3.722 (3), Cg5···Cg10(-1 + x, y, z) = 3.758 (3), Cg6···Cg9(x, y, z) = 3.705 (3) Å; where Cg1, Cg2, Cg5, Cg6, Cg9, Cg10, Cg13 and Cg14 are the centroids of N1/C1–C4/C9, C4–C9, N3/C19–C22/C27, C22–C27, N5/C37–C40/C45, C40–C45, N7/C55–C58/C63 and C58–C63 rings, respectively].