organic compounds
Ethyl 5-[(1H-benzoimidazol-2-yl)aminocarbonyl]-4-hydroxy-2-methyl-6-oxo-1-propyl-1,6-dihydropyridine-3-carboxylate–ethanol–methanol (4/2/1)
aSTC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine, and bNational University of Pharmacy, 4 Blyukhera ave., Kharkiv 61002, Ukraine
*Correspondence e-mail: sveta@xray.isc.kharkov.com
The 20H22N4O5·2C2H6O·CH4O, contains two pyridine-3-carboxylate molecules, one ethanol molecule and one methanol molecule disordered about in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in both independent molecules are planar within 0.03 Å due to the formation of intramolecular O—H⋯O and N—H⋯O hydrogen bonds. The formation of these latter interactions also causes the redistribution of the electron density within the hydroxypyridone fragment, with the result that some bonds are elongated compared with values in the literature and some others are shorter. In the crystal phase, the pyridine-3-carboxylate molecules form layers parallel to (010), which are interlinked through hydrogen bonds mediated by the bridging solvate molecules. A terminal ethyl group in one of the molecules is disordered over two sites of equally occupancy.
of the title compound, 4CRelated literature
For general properties of N-acylic derivatives of 2-aminobenzoimidazole, see: Ukrainets et al. (1993, 2006). For the geometrical properties of related compounds, see: Bürgi & Dunitz (1994); Low & Wilson (1983).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809026816/bg2271sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809026816/bg2271Isup2.hkl
A mixture of diethyl 4-hydroxy-2-methyl-6-oxo-1-propyl-1,6-dihydro- pyridine-3,5-dicarboxylate (Ukrainets et al., 2006) (3.11 g, 10.0 mmol), 2-aminobenzimidazole (1.33 g, 10.0 mmol), and DMF (1 ml) was stirred an kept on a metal bath at 160%A C for 5 min. The mixture was cooled, ethanol (30 ml) was added, the mixture was thoroughly mixed and filtered. The amino-ester obtained was washed on the filter with ethanol and dried. Yield 3.58 g (83%). m.p. 154–156%A C.
Crystals were multiple and poorly diffracting: in the specimen used no reflections appeared above 2θ = 50°, for what this was taken as the integration limit. Besides, some reflections were rejected in the integration process due to overlap with minor components. Restrictions on bond lengths (Csp3—Csp3 1.54 (1) Å, Csp3—O 1.43 (1) Å) in the solvate molecules and the disordered fragment were applied during The occupation factor for the latter group were refined for a few cycles, rounded up and kept fixed for the rest of the process. Hydrogen atoms were located from electron density difference maps and further idealized, or were calculated geometrically for the disordered fragment and solvate molecules, and were refined in the riding motion approximation with Uiso constrained to be 1.5 times Ueq of the for the methyl and hydroxyl groups and 1.2 times Ueq of the for the other atoms.
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell
CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Molecular view of the title compound with atomic labelling. All atoms are shown with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms and minor components of disordered ethyl group in molecule A omitted for clarity. | |
Fig. 2. The packing of the molecules in the crystal phase. Hydrogen bonds between molecules of (I) and bridging solvate molecules are shown by dashed lines. |
4C20H22N4O5·2C2H6O·CH4O | Z = 1 |
Mr = 1717.84 | F(000) = 910 |
Triclinic, P1 | Dx = 1.303 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5527 (4) Å | Cell parameters from 6420 reflections |
b = 13.9720 (4) Å | θ = 2.7–32.1° |
c = 16.0242 (5) Å | µ = 0.10 mm−1 |
α = 86.804 (3)° | T = 293 K |
β = 70.980 (3)° | Plate, colourless |
γ = 78.652 (3)° | 0.40 × 0.30 × 0.10 mm |
V = 2189.90 (12) Å3 |
Oxford Diffraction Xcalibur3 diffractometer | 3785 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 2.8° |
Detector resolution: 16.1827 pixels mm-1 | h = −12→12 |
ω scans | k = −16→16 |
23866 measured reflections | l = −19→19 |
7499 independent reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.1051P)2] where P = (Fo2 + 2Fc2)/3 |
7499 reflections | (Δ/σ)max = 0.001 |
596 parameters | Δρmax = 0.44 e Å−3 |
9 restraints | Δρmin = −0.35 e Å−3 |
4C20H22N4O5·2C2H6O·CH4O | γ = 78.652 (3)° |
Mr = 1717.84 | V = 2189.90 (12) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.5527 (4) Å | Mo Kα radiation |
b = 13.9720 (4) Å | µ = 0.10 mm−1 |
c = 16.0242 (5) Å | T = 293 K |
α = 86.804 (3)° | 0.40 × 0.30 × 0.10 mm |
β = 70.980 (3)° |
Oxford Diffraction Xcalibur3 diffractometer | 3785 reflections with I > 2σ(I) |
23866 measured reflections | Rint = 0.030 |
7499 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 9 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.44 e Å−3 |
7499 reflections | Δρmin = −0.35 e Å−3 |
596 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.8136 (6) | −0.0281 (4) | 0.5379 (4) | 0.1256 (19) | 0.50 |
H1 | 0.7474 | 0.0031 | 0.5752 | 0.188* | 0.50 |
C1 | 0.9280 (7) | 0.0168 (6) | 0.5292 (5) | 0.104 (3) | 0.50 |
H13 | 1.0073 | −0.0184 | 0.4859 | 0.156* | 0.50 |
H12 | 0.9102 | 0.0834 | 0.5112 | 0.156* | 0.50 |
H11 | 0.9436 | 0.0148 | 0.5851 | 0.156* | 0.50 |
O2 | 0.7030 (3) | 0.5258 (2) | −0.04837 (18) | 0.1089 (9) | |
H2 | 0.7304 | 0.5775 | −0.0542 | 0.163* | |
C2 | 0.6397 (5) | 0.5185 (4) | −0.1135 (3) | 0.1353 (17) | |
H22 | 0.5414 | 0.5338 | −0.0861 | 0.162* | |
H21 | 0.6637 | 0.4517 | −0.1349 | 0.162* | |
C3 | 0.6811 (5) | 0.5866 (4) | −0.1923 (3) | 0.1401 (19) | |
H33 | 0.6254 | 0.5856 | −0.2291 | 0.210* | |
H32 | 0.7753 | 0.5648 | −0.2260 | 0.210* | |
H31 | 0.6683 | 0.6519 | −0.1712 | 0.210* | |
O1A | 0.93576 (19) | 0.61024 (15) | 0.32098 (12) | 0.0634 (5) | |
H1A | 0.9905 | 0.6073 | 0.2709 | 0.095* | |
O2A | 0.61620 (18) | 0.64723 (13) | 0.16678 (12) | 0.0577 (5) | |
O3A | 1.0200 (2) | 0.62015 (14) | 0.15611 (12) | 0.0619 (5) | |
O4A | 0.6881 (3) | 0.55814 (18) | 0.53908 (16) | 0.1086 (10) | |
O5A | 0.8100 (2) | 0.67441 (14) | 0.49024 (12) | 0.0663 (6) | |
N1A | 0.5464 (2) | 0.63870 (14) | 0.31662 (13) | 0.0470 (5) | |
N2A | 0.8745 (2) | 0.62809 (14) | 0.07776 (13) | 0.0491 (5) | |
H2A | 0.7905 | 0.6334 | 0.0810 | 0.059* | |
N3A | 1.1051 (2) | 0.61149 (14) | −0.02264 (14) | 0.0507 (5) | |
H3A | 1.1476 | 0.6071 | 0.0154 | 0.061* | |
N4A | 0.9310 (2) | 0.62716 (15) | −0.07671 (14) | 0.0518 (6) | |
C1A | 0.5712 (3) | 0.63431 (17) | 0.39529 (16) | 0.0464 (6) | |
C2A | 0.7019 (3) | 0.62597 (17) | 0.39704 (16) | 0.0478 (6) | |
C3A | 0.8109 (3) | 0.62374 (17) | 0.31688 (16) | 0.0454 (6) | |
C4A | 0.7849 (3) | 0.63165 (16) | 0.23636 (15) | 0.0439 (6) | |
C5A | 0.6497 (3) | 0.64032 (16) | 0.23452 (17) | 0.0432 (6) | |
C6A | 0.9007 (3) | 0.62683 (17) | 0.15455 (17) | 0.0469 (6) | |
C7A | 0.9693 (3) | 0.62164 (16) | −0.00579 (16) | 0.0452 (6) | |
C8A | 1.1622 (3) | 0.60966 (17) | −0.11410 (17) | 0.0493 (7) | |
C9A | 1.2972 (3) | 0.60238 (19) | −0.16880 (19) | 0.0610 (8) | |
H9A | 1.3695 | 0.5956 | −0.1465 | 0.073* | |
C10A | 1.3164 (3) | 0.60597 (19) | −0.2586 (2) | 0.0650 (8) | |
H10A | 1.4045 | 0.6019 | −0.2979 | 0.078* | |
C11A | 1.2089 (3) | 0.61542 (19) | −0.29163 (19) | 0.0622 (8) | |
H11A | 1.2267 | 0.6175 | −0.3524 | 0.075* | |
C12A | 1.0771 (3) | 0.62182 (19) | −0.23733 (18) | 0.0596 (7) | |
H12A | 1.0057 | 0.6276 | −0.2604 | 0.072* | |
C13A | 1.0530 (3) | 0.61940 (17) | −0.14619 (17) | 0.0480 (6) | |
C14A | 0.4088 (3) | 0.6390 (2) | 0.31050 (19) | 0.0567 (7) | |
H14B | 0.3559 | 0.6091 | 0.3630 | 0.068* | |
H14A | 0.4185 | 0.5996 | 0.2600 | 0.068* | |
C15A | 0.3321 (3) | 0.7395 (2) | 0.3014 (2) | 0.0699 (8) | |
H15B | 0.3144 | 0.7773 | 0.3543 | 0.084* | |
H15A | 0.3880 | 0.7719 | 0.2519 | 0.084* | |
C16A | 0.1993 (3) | 0.7370 (3) | 0.2871 (3) | 0.0963 (11) | |
H16C | 0.1430 | 0.7058 | 0.3363 | 0.144* | |
H16B | 0.2164 | 0.7010 | 0.2339 | 0.144* | |
H16A | 0.1533 | 0.8024 | 0.2819 | 0.144* | |
C17A | 0.7317 (3) | 0.6147 (2) | 0.48234 (18) | 0.0608 (8) | |
C18A | 0.8539 (4) | 0.6630 (3) | 0.5673 (2) | 0.0959 (12) | |
H18A | 0.8992 | 0.5962 | 0.5711 | 0.115* | 0.50 |
H18B | 0.7759 | 0.6785 | 0.6203 | 0.115* | 0.50 |
H18E | 0.8463 | 0.5990 | 0.5928 | 0.115* | 0.25 |
H18F | 0.7993 | 0.7123 | 0.6115 | 0.115* | 0.25 |
H18G | 0.7882 | 0.6362 | 0.6156 | 0.115* | 0.25 |
H18H | 0.8628 | 0.7256 | 0.5858 | 0.115* | 0.25 |
C19A | 0.9530 (10) | 0.7334 (8) | 0.5579 (7) | 0.107 (4) | 0.50 |
H19A | 0.9841 | 0.7275 | 0.6083 | 0.161* | 0.50 |
H19B | 0.9070 | 0.7992 | 0.5542 | 0.161* | 0.50 |
H19C | 1.0298 | 0.7173 | 0.5053 | 0.161* | 0.50 |
C19C | 1.0040 (8) | 0.6754 (17) | 0.5334 (12) | 0.098 (7) | 0.25 |
H19G | 1.0080 | 0.7426 | 0.5190 | 0.146* | 0.25 |
H19H | 1.0521 | 0.6356 | 0.4816 | 0.146* | 0.25 |
H19I | 1.0454 | 0.6558 | 0.5783 | 0.146* | 0.25 |
C19D | 0.9929 (14) | 0.5928 (15) | 0.5406 (10) | 0.129 (7) | 0.25 |
H19J | 0.9796 | 0.5276 | 0.5575 | 0.194* | 0.25 |
H19K | 1.0502 | 0.6121 | 0.5699 | 0.194* | 0.25 |
H19L | 1.0357 | 0.5950 | 0.4779 | 0.194* | 0.25 |
C20A | 0.4504 (3) | 0.6403 (2) | 0.47764 (18) | 0.0637 (8) | |
H20C | 0.3804 | 0.6940 | 0.4734 | 0.095* | |
H20B | 0.4775 | 0.6500 | 0.5277 | 0.095* | |
H20A | 0.4158 | 0.5807 | 0.4845 | 0.095* | |
O1B | 0.5138 (2) | 0.15276 (16) | 0.20358 (12) | 0.0661 (5) | |
H1B | 0.4590 | 0.1567 | 0.2537 | 0.099* | |
O2B | 0.83685 (19) | 0.12699 (14) | 0.35437 (12) | 0.0621 (5) | |
O3B | 0.4315 (2) | 0.14907 (14) | 0.36909 (11) | 0.0626 (5) | |
O4B | 0.7561 (3) | 0.0800 (2) | −0.01009 (16) | 0.1132 (10) | |
O5B | 0.6275 (2) | 0.22567 (15) | 0.03465 (13) | 0.0774 (6) | |
N1B | 0.9037 (2) | 0.13316 (15) | 0.20430 (13) | 0.0495 (5) | |
N2B | 0.5847 (2) | 0.12074 (14) | 0.44403 (12) | 0.0470 (5) | |
H2B | 0.6698 | 0.1119 | 0.4392 | 0.056* | |
N3B | 0.3573 (2) | 0.12625 (14) | 0.54523 (13) | 0.0469 (5) | |
H3B | 0.3142 | 0.1335 | 0.5074 | 0.056* | |
N4B | 0.5335 (2) | 0.10497 (15) | 0.59801 (13) | 0.0496 (5) | |
C1B | 0.8763 (3) | 0.13635 (17) | 0.12602 (16) | 0.0501 (7) | |
C2B | 0.7451 (3) | 0.14426 (17) | 0.12605 (16) | 0.0477 (6) | |
C3B | 0.6372 (3) | 0.14685 (17) | 0.20741 (16) | 0.0454 (6) | |
C4B | 0.6659 (3) | 0.13928 (16) | 0.28656 (15) | 0.0423 (6) | |
C5B | 0.8017 (3) | 0.13273 (17) | 0.28661 (16) | 0.0449 (6) | |
C6B | 0.5526 (3) | 0.13693 (17) | 0.36914 (16) | 0.0466 (6) | |
C7B | 0.4930 (3) | 0.11702 (16) | 0.52847 (16) | 0.0439 (6) | |
C8B | 0.3012 (3) | 0.12150 (17) | 0.63690 (16) | 0.0454 (6) | |
C9B | 0.1684 (3) | 0.1288 (2) | 0.69188 (18) | 0.0568 (7) | |
H9B | 0.0954 | 0.1380 | 0.6701 | 0.068* | |
C10B | 0.1500 (3) | 0.1216 (2) | 0.78080 (19) | 0.0612 (8) | |
H10B | 0.0620 | 0.1263 | 0.8202 | 0.073* | |
C11B | 0.2572 (3) | 0.1078 (2) | 0.81315 (18) | 0.0589 (7) | |
H11B | 0.2398 | 0.1037 | 0.8739 | 0.071* | |
C12B | 0.3898 (3) | 0.09979 (19) | 0.75866 (17) | 0.0553 (7) | |
H12B | 0.4622 | 0.0891 | 0.7813 | 0.066* | |
C13B | 0.4118 (3) | 0.10834 (17) | 0.66814 (16) | 0.0446 (6) | |
C14B | 1.0427 (3) | 0.1290 (2) | 0.20801 (19) | 0.0586 (7) | |
H14D | 1.0369 | 0.1665 | 0.2587 | 0.070* | |
H14C | 1.0953 | 0.1592 | 0.1555 | 0.070* | |
C15B | 1.1158 (3) | 0.0272 (2) | 0.2143 (2) | 0.0689 (8) | |
H15D | 1.1263 | −0.0096 | 0.1622 | 0.083* | |
H15C | 1.0619 | −0.0042 | 0.2654 | 0.083* | |
C16B | 1.2553 (4) | 0.0263 (3) | 0.2224 (3) | 0.1056 (13) | |
H16F | 1.3074 | 0.0599 | 0.1733 | 0.158* | |
H16E | 1.3020 | −0.0399 | 0.2228 | 0.158* | |
H16D | 1.2447 | 0.0584 | 0.2764 | 0.158* | |
C17B | 0.7118 (3) | 0.1451 (2) | 0.04263 (18) | 0.0646 (8) | |
C18B | 0.5741 (4) | 0.2295 (3) | −0.0391 (2) | 0.1005 (12) | |
H18D | 0.6441 | 0.1966 | −0.0901 | 0.121* | |
H18C | 0.5483 | 0.2969 | −0.0546 | 0.121* | |
C19B | 0.4490 (4) | 0.1798 (3) | −0.0134 (3) | 0.1195 (15) | |
H19F | 0.4750 | 0.1130 | 0.0015 | 0.179* | |
H19E | 0.4146 | 0.1822 | −0.0622 | 0.179* | |
H19D | 0.3793 | 0.2132 | 0.0365 | 0.179* | |
C20B | 0.9947 (3) | 0.1321 (2) | 0.04247 (17) | 0.0620 (8) | |
H20F | 0.9628 | 0.1339 | −0.0074 | 0.093* | |
H20E | 1.0593 | 0.0727 | 0.0407 | 0.093* | |
H20D | 1.0379 | 0.1869 | 0.0406 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.101 (5) | 0.156 (5) | 0.125 (5) | −0.011 (4) | −0.047 (4) | −0.017 (4) |
C1 | 0.079 (5) | 0.173 (8) | 0.062 (5) | −0.006 (6) | −0.039 (4) | 0.014 (5) |
O2 | 0.098 (2) | 0.142 (2) | 0.0954 (19) | −0.0334 (19) | −0.0382 (16) | 0.0141 (17) |
C2 | 0.130 (4) | 0.168 (4) | 0.140 (4) | −0.030 (3) | −0.088 (4) | 0.005 (4) |
C3 | 0.123 (4) | 0.218 (5) | 0.106 (3) | −0.073 (4) | −0.055 (3) | 0.036 (4) |
O1A | 0.0518 (13) | 0.0949 (14) | 0.0495 (11) | −0.0165 (11) | −0.0226 (9) | −0.0021 (11) |
O2A | 0.0486 (11) | 0.0806 (12) | 0.0461 (11) | −0.0094 (10) | −0.0201 (9) | 0.0013 (9) |
O3A | 0.0469 (12) | 0.0902 (14) | 0.0488 (11) | −0.0154 (10) | −0.0135 (9) | −0.0049 (9) |
O4A | 0.165 (3) | 0.1181 (19) | 0.0764 (16) | −0.0805 (19) | −0.0612 (17) | 0.0487 (15) |
O5A | 0.0851 (15) | 0.0796 (13) | 0.0487 (11) | −0.0282 (12) | −0.0345 (11) | 0.0049 (9) |
N1A | 0.0458 (14) | 0.0497 (12) | 0.0455 (13) | −0.0111 (10) | −0.0133 (11) | 0.0000 (9) |
N2A | 0.0455 (14) | 0.0633 (13) | 0.0397 (13) | −0.0116 (11) | −0.0144 (11) | 0.0010 (10) |
N3A | 0.0497 (15) | 0.0588 (13) | 0.0433 (13) | −0.0082 (11) | −0.0163 (11) | 0.0026 (10) |
N4A | 0.0543 (15) | 0.0599 (13) | 0.0421 (13) | −0.0104 (11) | −0.0166 (11) | −0.0010 (10) |
C1A | 0.0564 (18) | 0.0459 (14) | 0.0375 (14) | −0.0170 (13) | −0.0117 (13) | 0.0006 (11) |
C2A | 0.0608 (19) | 0.0454 (14) | 0.0415 (15) | −0.0173 (13) | −0.0183 (14) | 0.0031 (11) |
C3A | 0.0476 (17) | 0.0447 (14) | 0.0473 (15) | −0.0126 (12) | −0.0177 (13) | −0.0001 (11) |
C4A | 0.0479 (17) | 0.0436 (13) | 0.0410 (14) | −0.0095 (12) | −0.0149 (12) | −0.0006 (11) |
C5A | 0.0421 (16) | 0.0444 (14) | 0.0434 (15) | −0.0084 (12) | −0.0138 (13) | −0.0007 (11) |
C6A | 0.0456 (17) | 0.0496 (14) | 0.0459 (16) | −0.0090 (12) | −0.0150 (13) | −0.0013 (11) |
C7A | 0.0462 (17) | 0.0444 (14) | 0.0447 (16) | −0.0107 (12) | −0.0132 (13) | 0.0017 (11) |
C8A | 0.0530 (18) | 0.0456 (14) | 0.0432 (15) | −0.0104 (13) | −0.0061 (14) | −0.0014 (11) |
C9A | 0.0568 (19) | 0.0632 (17) | 0.0613 (19) | −0.0146 (15) | −0.0148 (16) | −0.0011 (14) |
C10A | 0.065 (2) | 0.0574 (17) | 0.0575 (19) | −0.0117 (15) | −0.0001 (17) | 0.0017 (14) |
C11A | 0.074 (2) | 0.0570 (17) | 0.0461 (17) | −0.0107 (16) | −0.0081 (17) | 0.0026 (13) |
C12A | 0.074 (2) | 0.0584 (16) | 0.0443 (16) | −0.0114 (15) | −0.0167 (16) | 0.0019 (13) |
C13A | 0.0531 (18) | 0.0440 (14) | 0.0440 (15) | −0.0084 (12) | −0.0120 (14) | 0.0005 (11) |
C14A | 0.0465 (17) | 0.0657 (17) | 0.0585 (17) | −0.0180 (14) | −0.0133 (14) | −0.0005 (13) |
C15A | 0.058 (2) | 0.075 (2) | 0.079 (2) | −0.0153 (16) | −0.0236 (17) | −0.0028 (16) |
C16A | 0.052 (2) | 0.118 (3) | 0.120 (3) | −0.019 (2) | −0.029 (2) | 0.000 (2) |
C17A | 0.074 (2) | 0.0634 (17) | 0.0479 (17) | −0.0168 (16) | −0.0222 (16) | 0.0069 (14) |
C18A | 0.118 (3) | 0.130 (3) | 0.057 (2) | −0.022 (3) | −0.051 (2) | −0.003 (2) |
C19A | 0.152 (9) | 0.124 (8) | 0.090 (7) | −0.065 (7) | −0.076 (6) | 0.003 (6) |
C19C | 0.135 (17) | 0.103 (16) | 0.107 (16) | −0.062 (14) | −0.089 (14) | 0.021 (13) |
C19D | 0.103 (15) | 0.21 (2) | 0.097 (13) | −0.015 (16) | −0.075 (12) | 0.031 (14) |
C20A | 0.065 (2) | 0.0704 (18) | 0.0517 (17) | −0.0201 (16) | −0.0096 (15) | −0.0001 (14) |
O1B | 0.0506 (13) | 0.1019 (15) | 0.0473 (11) | −0.0132 (11) | −0.0191 (9) | 0.0058 (11) |
O2B | 0.0503 (12) | 0.0938 (14) | 0.0428 (11) | −0.0131 (10) | −0.0158 (9) | −0.0005 (10) |
O3B | 0.0459 (12) | 0.0921 (14) | 0.0451 (11) | −0.0093 (10) | −0.0110 (9) | 0.0031 (9) |
O4B | 0.135 (2) | 0.124 (2) | 0.0706 (16) | 0.0405 (18) | −0.0494 (16) | −0.0471 (15) |
O5B | 0.0963 (17) | 0.0793 (14) | 0.0563 (12) | 0.0021 (13) | −0.0361 (12) | 0.0090 (10) |
N1B | 0.0418 (13) | 0.0587 (13) | 0.0433 (13) | −0.0083 (10) | −0.0079 (10) | 0.0002 (10) |
N2B | 0.0383 (12) | 0.0632 (13) | 0.0355 (12) | −0.0065 (10) | −0.0078 (10) | −0.0026 (10) |
N3B | 0.0404 (13) | 0.0600 (13) | 0.0396 (12) | −0.0076 (10) | −0.0125 (10) | −0.0022 (9) |
N4B | 0.0455 (14) | 0.0619 (13) | 0.0379 (12) | −0.0119 (11) | −0.0075 (11) | −0.0014 (10) |
C1B | 0.060 (2) | 0.0448 (14) | 0.0390 (15) | −0.0048 (13) | −0.0100 (13) | 0.0027 (11) |
C2B | 0.0543 (18) | 0.0487 (14) | 0.0363 (14) | −0.0011 (13) | −0.0143 (13) | −0.0012 (11) |
C3B | 0.0486 (17) | 0.0464 (14) | 0.0410 (15) | −0.0072 (12) | −0.0149 (13) | −0.0016 (11) |
C4B | 0.0495 (17) | 0.0408 (13) | 0.0340 (13) | −0.0077 (12) | −0.0101 (12) | −0.0016 (10) |
C5B | 0.0411 (16) | 0.0509 (15) | 0.0390 (15) | −0.0064 (12) | −0.0092 (13) | 0.0009 (11) |
C6B | 0.0485 (18) | 0.0477 (14) | 0.0418 (15) | −0.0068 (13) | −0.0128 (13) | −0.0038 (11) |
C7B | 0.0437 (16) | 0.0440 (14) | 0.0405 (15) | −0.0096 (12) | −0.0079 (13) | −0.0020 (11) |
C8B | 0.0459 (16) | 0.0456 (14) | 0.0405 (14) | −0.0082 (12) | −0.0083 (13) | −0.0015 (11) |
C9B | 0.0425 (17) | 0.0750 (18) | 0.0515 (17) | −0.0170 (14) | −0.0100 (14) | 0.0013 (14) |
C10B | 0.0529 (19) | 0.0715 (18) | 0.0512 (18) | −0.0178 (15) | −0.0016 (15) | −0.0046 (14) |
C11B | 0.066 (2) | 0.0674 (17) | 0.0369 (15) | −0.0182 (15) | −0.0051 (15) | 0.0001 (13) |
C12B | 0.0562 (19) | 0.0634 (17) | 0.0446 (16) | −0.0141 (14) | −0.0119 (14) | −0.0017 (13) |
C13B | 0.0489 (17) | 0.0452 (14) | 0.0363 (14) | −0.0100 (12) | −0.0082 (13) | −0.0024 (11) |
C14B | 0.0518 (17) | 0.0687 (18) | 0.0515 (16) | −0.0154 (15) | −0.0090 (14) | −0.0001 (13) |
C15B | 0.057 (2) | 0.078 (2) | 0.067 (2) | −0.0133 (16) | −0.0121 (16) | −0.0038 (15) |
C16B | 0.059 (2) | 0.123 (3) | 0.138 (4) | −0.021 (2) | −0.037 (2) | 0.014 (3) |
C17B | 0.068 (2) | 0.081 (2) | 0.0361 (16) | −0.0040 (18) | −0.0108 (15) | −0.0032 (15) |
C18B | 0.126 (3) | 0.118 (3) | 0.062 (2) | −0.001 (2) | −0.051 (2) | 0.012 (2) |
C19B | 0.140 (4) | 0.147 (4) | 0.101 (3) | −0.032 (3) | −0.077 (3) | 0.013 (3) |
C20B | 0.062 (2) | 0.0698 (18) | 0.0427 (16) | −0.0084 (15) | −0.0031 (14) | 0.0028 (13) |
O1—C1 | 1.4313 (10) | C18A—H18H | 0.9700 |
O1—H1 | 0.8200 | C19A—H19A | 0.9600 |
C1—C1i | 1.500 (14) | C19A—H19B | 0.9600 |
C1—H13 | 0.9600 | C19A—H19C | 0.9600 |
C1—H12 | 0.9601 | C19C—H19G | 0.9600 |
C1—H11 | 0.9599 | C19C—H19H | 0.9600 |
O2—C2 | 1.428 (6) | C19C—H19I | 0.9600 |
O2—H2 | 0.8200 | C19D—H19J | 0.9600 |
C2—C3 | 1.537 (7) | C19D—H19K | 0.9600 |
C2—H22 | 0.9700 | C19D—H19L | 0.9600 |
C2—H21 | 0.9700 | C20A—H20C | 0.9600 |
C3—H33 | 0.9600 | C20A—H20B | 0.9600 |
C3—H32 | 0.9600 | C20A—H20A | 0.9600 |
C3—H31 | 0.9600 | O1B—C3B | 1.310 (3) |
O1A—C3A | 1.316 (3) | O1B—H1B | 0.8200 |
O1A—H1A | 0.8200 | O2B—C5B | 1.250 (3) |
O2A—C5A | 1.240 (3) | O3B—C6B | 1.256 (3) |
O3A—C6A | 1.252 (3) | O4B—C17B | 1.191 (3) |
O4A—C17A | 1.205 (3) | O5B—C17B | 1.319 (4) |
O5A—C17A | 1.322 (3) | O5B—C18B | 1.461 (4) |
O5A—C18A | 1.444 (3) | N1B—C1B | 1.373 (3) |
N1A—C1A | 1.364 (3) | N1B—C5B | 1.405 (3) |
N1A—C5A | 1.411 (3) | N1B—C14B | 1.478 (3) |
N1A—C14A | 1.486 (3) | N2B—C6B | 1.345 (3) |
N2A—C6A | 1.345 (3) | N2B—C7B | 1.388 (3) |
N2A—C7A | 1.380 (3) | N2B—H2B | 0.8600 |
N2A—H2A | 0.8600 | N3B—C7B | 1.350 (3) |
N3A—C7A | 1.349 (3) | N3B—C8B | 1.396 (3) |
N3A—C8A | 1.391 (3) | N3B—H3B | 0.8600 |
N3A—H3A | 0.8600 | N4B—C7B | 1.309 (3) |
N4A—C7A | 1.318 (3) | N4B—C13B | 1.399 (3) |
N4A—C13A | 1.390 (3) | C1B—C2B | 1.367 (4) |
C1A—C2A | 1.371 (4) | C1B—C20B | 1.499 (4) |
C1A—C20A | 1.499 (4) | C2B—C3B | 1.421 (3) |
C2A—C3A | 1.415 (4) | C2B—C17B | 1.488 (4) |
C2A—C17A | 1.493 (4) | C3B—C4B | 1.391 (3) |
C3A—C4A | 1.399 (3) | C4B—C5B | 1.418 (4) |
C4A—C5A | 1.417 (3) | C4B—C6B | 1.470 (3) |
C4A—C6A | 1.466 (4) | C8B—C9B | 1.378 (4) |
C8A—C13A | 1.388 (4) | C8B—C13B | 1.391 (4) |
C8A—C9A | 1.395 (4) | C9B—C10B | 1.375 (4) |
C9A—C10A | 1.386 (4) | C9B—H9B | 0.9300 |
C9A—H9A | 0.9300 | C10B—C11B | 1.368 (4) |
C10A—C11A | 1.381 (4) | C10B—H10B | 0.9300 |
C10A—H10A | 0.9300 | C11B—C12B | 1.373 (4) |
C11A—C12A | 1.368 (4) | C11B—H11B | 0.9300 |
C11A—H11A | 0.9300 | C12B—C13B | 1.394 (3) |
C12A—C13A | 1.398 (4) | C12B—H12B | 0.9300 |
C12A—H12A | 0.9300 | C14B—C15B | 1.494 (4) |
C14A—C15A | 1.502 (4) | C14B—H14D | 0.9700 |
C14A—H14B | 0.9700 | C14B—H14C | 0.9700 |
C14A—H14A | 0.9700 | C15B—C16B | 1.516 (4) |
C15A—C16A | 1.499 (4) | C15B—H15D | 0.9700 |
C15A—H15B | 0.9700 | C15B—H15C | 0.9700 |
C15A—H15A | 0.9700 | C16B—H16F | 0.9600 |
C16A—H16C | 0.9600 | C16B—H16E | 0.9600 |
C16A—H16B | 0.9600 | C16B—H16D | 0.9600 |
C16A—H16A | 0.9600 | C18B—C19B | 1.539 (6) |
C18A—C19A | 1.5390 (10) | C18B—H18D | 0.9700 |
C18A—C19D | 1.5396 (11) | C18B—H18C | 0.9700 |
C18A—C19C | 1.5396 (11) | C19B—H19F | 0.9600 |
C18A—H18A | 0.9700 | C19B—H19E | 0.9600 |
C18A—H18B | 0.9700 | C19B—H19D | 0.9600 |
C18A—H18E | 0.9700 | C20B—H20F | 0.9600 |
C18A—H18F | 0.9700 | C20B—H20E | 0.9600 |
C18A—H18G | 0.9700 | C20B—H20D | 0.9600 |
C1—O1—H1 | 107.4 | H18A—C18A—H18G | 76.3 |
O1—C1—C1i | 126.6 (9) | H18F—C18A—H18G | 68.3 |
O1—C1—H13 | 109.2 | O5A—C18A—H18H | 110.4 |
O1—C1—H12 | 110.2 | C19D—C18A—H18H | 110.4 |
C1i—C1—H12 | 101.3 | C19C—C18A—H18H | 69.3 |
H13—C1—H12 | 109.5 | H18A—C18A—H18H | 133.8 |
O1—C1—H11 | 109.0 | H18B—C18A—H18H | 76.6 |
C1i—C1—H11 | 99.1 | H18E—C18A—H18H | 137.0 |
H13—C1—H11 | 109.5 | H18G—C18A—H18H | 108.6 |
H12—C1—H11 | 109.5 | C18A—C19A—H19A | 109.5 |
C2—O2—H2 | 109.5 | C18A—C19A—H19B | 109.5 |
O2—C2—C3 | 113.5 (3) | H19A—C19A—H19B | 109.5 |
O2—C2—H22 | 108.9 | C18A—C19A—H19C | 109.5 |
C3—C2—H22 | 108.9 | H19A—C19A—H19C | 109.5 |
O2—C2—H21 | 108.9 | H19B—C19A—H19C | 109.5 |
C3—C2—H21 | 108.9 | C18A—C19C—H19G | 109.5 |
H22—C2—H21 | 107.7 | C18A—C19C—H19H | 109.5 |
C2—C3—H33 | 109.5 | H19G—C19C—H19H | 109.5 |
C2—C3—H32 | 109.5 | C18A—C19C—H19I | 109.5 |
H33—C3—H32 | 109.5 | H19G—C19C—H19I | 109.5 |
C2—C3—H31 | 109.5 | H19H—C19C—H19I | 109.5 |
H33—C3—H31 | 109.5 | C18A—C19D—H19J | 109.5 |
H32—C3—H31 | 109.5 | C18A—C19D—H19K | 109.5 |
C3A—O1A—H1A | 109.5 | H19J—C19D—H19K | 109.5 |
C17A—O5A—C18A | 116.9 (2) | C18A—C19D—H19L | 109.5 |
C1A—N1A—C5A | 122.9 (2) | H19J—C19D—H19L | 109.5 |
C1A—N1A—C14A | 122.5 (2) | H19K—C19D—H19L | 109.5 |
C5A—N1A—C14A | 114.6 (2) | C1A—C20A—H20C | 109.5 |
C6A—N2A—C7A | 126.5 (2) | C1A—C20A—H20B | 109.5 |
C6A—N2A—H2A | 116.8 | H20C—C20A—H20B | 109.5 |
C7A—N2A—H2A | 116.8 | C1A—C20A—H20A | 109.5 |
C7A—N3A—C8A | 105.9 (2) | H20C—C20A—H20A | 109.5 |
C7A—N3A—H3A | 127.1 | H20B—C20A—H20A | 109.5 |
C8A—N3A—H3A | 127.1 | C3B—O1B—H1B | 109.5 |
C7A—N4A—C13A | 103.8 (2) | C17B—O5B—C18B | 116.8 (2) |
N1A—C1A—C2A | 120.2 (2) | C1B—N1B—C5B | 122.4 (2) |
N1A—C1A—C20A | 117.2 (2) | C1B—N1B—C14B | 122.4 (2) |
C2A—C1A—C20A | 122.6 (2) | C5B—N1B—C14B | 115.2 (2) |
C1A—C2A—C3A | 119.7 (2) | C6B—N2B—C7B | 126.0 (2) |
C1A—C2A—C17A | 120.8 (2) | C6B—N2B—H2B | 117.0 |
C3A—C2A—C17A | 119.4 (3) | C7B—N2B—H2B | 117.0 |
O1A—C3A—C4A | 122.0 (2) | C7B—N3B—C8B | 105.7 (2) |
O1A—C3A—C2A | 118.0 (2) | C7B—N3B—H3B | 127.2 |
C4A—C3A—C2A | 120.0 (2) | C8B—N3B—H3B | 127.2 |
C3A—C4A—C5A | 120.3 (2) | C7B—N4B—C13B | 103.4 (2) |
C3A—C4A—C6A | 118.5 (2) | C2B—C1B—N1B | 120.2 (2) |
C5A—C4A—C6A | 121.2 (2) | C2B—C1B—C20B | 122.4 (2) |
O2A—C5A—N1A | 118.0 (2) | N1B—C1B—C20B | 117.4 (3) |
O2A—C5A—C4A | 125.2 (2) | C1B—C2B—C3B | 119.8 (2) |
N1A—C5A—C4A | 116.8 (2) | C1B—C2B—C17B | 121.8 (2) |
O3A—C6A—N2A | 121.2 (2) | C3B—C2B—C17B | 118.3 (3) |
O3A—C6A—C4A | 121.2 (2) | O1B—C3B—C4B | 122.8 (2) |
N2A—C6A—C4A | 117.6 (2) | O1B—C3B—C2B | 117.3 (2) |
N4A—C7A—N3A | 114.5 (2) | C4B—C3B—C2B | 119.8 (2) |
N4A—C7A—N2A | 121.1 (2) | C3B—C4B—C5B | 120.3 (2) |
N3A—C7A—N2A | 124.4 (2) | C3B—C4B—C6B | 118.3 (2) |
C13A—C8A—N3A | 105.5 (2) | C5B—C4B—C6B | 121.4 (2) |
C13A—C8A—C9A | 123.1 (2) | O2B—C5B—N1B | 117.9 (2) |
N3A—C8A—C9A | 131.4 (3) | O2B—C5B—C4B | 124.8 (2) |
C10A—C9A—C8A | 115.6 (3) | N1B—C5B—C4B | 117.3 (2) |
C10A—C9A—H9A | 122.2 | O3B—C6B—N2B | 121.9 (2) |
C8A—C9A—H9A | 122.2 | O3B—C6B—C4B | 121.0 (2) |
C11A—C10A—C9A | 122.1 (3) | N2B—C6B—C4B | 117.1 (2) |
C11A—C10A—H10A | 119.0 | N4B—C7B—N3B | 115.3 (2) |
C9A—C10A—H10A | 119.0 | N4B—C7B—N2B | 121.6 (2) |
C12A—C11A—C10A | 121.8 (3) | N3B—C7B—N2B | 123.2 (2) |
C12A—C11A—H11A | 119.1 | C9B—C8B—C13B | 122.8 (2) |
C10A—C11A—H11A | 119.1 | C9B—C8B—N3B | 132.0 (2) |
C11A—C12A—C13A | 118.0 (3) | C13B—C8B—N3B | 105.2 (2) |
C11A—C12A—H12A | 121.0 | C10B—C9B—C8B | 116.2 (3) |
C13A—C12A—H12A | 121.0 | C10B—C9B—H9B | 121.9 |
C8A—C13A—N4A | 110.3 (2) | C8B—C9B—H9B | 121.9 |
C8A—C13A—C12A | 119.5 (3) | C11B—C10B—C9B | 122.1 (3) |
N4A—C13A—C12A | 130.2 (3) | C11B—C10B—H10B | 119.0 |
N1A—C14A—C15A | 113.3 (2) | C9B—C10B—H10B | 119.0 |
N1A—C14A—H14B | 108.9 | C10B—C11B—C12B | 122.0 (3) |
C15A—C14A—H14B | 108.9 | C10B—C11B—H11B | 119.0 |
N1A—C14A—H14A | 108.9 | C12B—C11B—H11B | 119.0 |
C15A—C14A—H14A | 108.9 | C11B—C12B—C13B | 117.4 (3) |
H14B—C14A—H14A | 107.7 | C11B—C12B—H12B | 121.3 |
C16A—C15A—C14A | 112.1 (3) | C13B—C12B—H12B | 121.3 |
C16A—C15A—H15B | 109.2 | C8B—C13B—C12B | 119.5 (2) |
C14A—C15A—H15B | 109.2 | C8B—C13B—N4B | 110.5 (2) |
C16A—C15A—H15A | 109.2 | C12B—C13B—N4B | 130.1 (2) |
C14A—C15A—H15A | 109.2 | N1B—C14B—C15B | 112.9 (2) |
H15B—C15A—H15A | 107.9 | N1B—C14B—H14D | 109.0 |
C15A—C16A—H16C | 109.5 | C15B—C14B—H14D | 109.0 |
C15A—C16A—H16B | 109.5 | N1B—C14B—H14C | 109.0 |
H16C—C16A—H16B | 109.5 | C15B—C14B—H14C | 109.0 |
C15A—C16A—H16A | 109.5 | H14D—C14B—H14C | 107.8 |
H16C—C16A—H16A | 109.5 | C14B—C15B—C16B | 111.3 (3) |
H16B—C16A—H16A | 109.5 | C14B—C15B—H15D | 109.4 |
O4A—C17A—O5A | 122.9 (3) | C16B—C15B—H15D | 109.4 |
O4A—C17A—C2A | 124.1 (3) | C14B—C15B—H15C | 109.4 |
O5A—C17A—C2A | 113.0 (2) | C16B—C15B—H15C | 109.4 |
O5A—C18A—C19A | 107.5 (5) | H15D—C15B—H15C | 108.0 |
O5A—C18A—C19D | 106.6 (6) | C15B—C16B—H16F | 109.5 |
C19A—C18A—C19D | 78.2 (10) | C15B—C16B—H16E | 109.5 |
O5A—C18A—C19C | 104.9 (8) | H16F—C16B—H16E | 109.5 |
C19D—C18A—C19C | 45.0 (10) | C15B—C16B—H16D | 109.5 |
O5A—C18A—H18A | 110.2 | H16F—C16B—H16D | 109.5 |
C19A—C18A—H18A | 110.2 | H16E—C16B—H16D | 109.5 |
C19C—C18A—H18A | 79.8 | O4B—C17B—O5B | 124.5 (3) |
O5A—C18A—H18B | 110.2 | O4B—C17B—C2B | 123.6 (3) |
C19A—C18A—H18B | 110.2 | O5B—C17B—C2B | 112.0 (2) |
C19D—C18A—H18B | 137.0 | O5B—C18B—C19B | 109.9 (3) |
C19C—C18A—H18B | 137.6 | O5B—C18B—H18D | 109.7 |
H18A—C18A—H18B | 108.5 | C19B—C18B—H18D | 109.7 |
O5A—C18A—H18E | 110.8 | O5B—C18B—H18C | 109.7 |
C19A—C18A—H18E | 134.7 | C19B—C18B—H18C | 109.7 |
C19D—C18A—H18E | 68.4 | H18D—C18B—H18C | 108.2 |
C19C—C18A—H18E | 110.8 | C18B—C19B—H19F | 109.5 |
H18B—C18A—H18E | 78.2 | C18B—C19B—H19E | 109.5 |
O5A—C18A—H18F | 110.8 | H19F—C19B—H19E | 109.5 |
C19A—C18A—H18F | 78.4 | C18B—C19B—H19D | 109.5 |
C19D—C18A—H18F | 140.3 | H19F—C19B—H19D | 109.5 |
C19C—C18A—H18F | 110.8 | H19E—C19B—H19D | 109.5 |
H18A—C18A—H18F | 132.8 | C1B—C20B—H20F | 109.5 |
H18E—C18A—H18F | 108.8 | C1B—C20B—H20E | 109.5 |
O5A—C18A—H18G | 110.4 | H20F—C20B—H20E | 109.5 |
C19A—C18A—H18G | 136.2 | C1B—C20B—H20D | 109.5 |
C19D—C18A—H18G | 110.4 | H20F—C20B—H20D | 109.5 |
C19C—C18A—H18G | 142.4 | H20E—C20B—H20D | 109.5 |
C5A—N1A—C1A—C2A | −3.5 (3) | C17A—O5A—C18A—C19C | 139.4 (9) |
C14A—N1A—C1A—C2A | 174.5 (2) | C5B—N1B—C1B—C2B | 3.3 (3) |
C5A—N1A—C1A—C20A | 175.7 (2) | C14B—N1B—C1B—C2B | −177.2 (2) |
C14A—N1A—C1A—C20A | −6.2 (3) | C5B—N1B—C1B—C20B | −177.4 (2) |
N1A—C1A—C2A—C3A | 1.2 (3) | C14B—N1B—C1B—C20B | 2.0 (3) |
C20A—C1A—C2A—C3A | −178.0 (2) | N1B—C1B—C2B—C3B | −1.5 (4) |
N1A—C1A—C2A—C17A | −176.1 (2) | C20B—C1B—C2B—C3B | 179.3 (2) |
C20A—C1A—C2A—C17A | 4.7 (4) | N1B—C1B—C2B—C17B | −178.2 (2) |
C1A—C2A—C3A—O1A | −176.3 (2) | C20B—C1B—C2B—C17B | 2.6 (4) |
C17A—C2A—C3A—O1A | 1.0 (3) | C1B—C2B—C3B—O1B | −178.8 (2) |
C1A—C2A—C3A—C4A | 1.1 (3) | C17B—C2B—C3B—O1B | −2.0 (4) |
C17A—C2A—C3A—C4A | 178.3 (2) | C1B—C2B—C3B—C4B | −1.3 (4) |
O1A—C3A—C4A—C5A | 176.2 (2) | C17B—C2B—C3B—C4B | 175.5 (2) |
C2A—C3A—C4A—C5A | −1.0 (3) | O1B—C3B—C4B—C5B | 179.8 (2) |
O1A—C3A—C4A—C6A | −1.4 (3) | C2B—C3B—C4B—C5B | 2.4 (3) |
C2A—C3A—C4A—C6A | −178.6 (2) | O1B—C3B—C4B—C6B | 0.6 (3) |
C1A—N1A—C5A—O2A | −177.9 (2) | C2B—C3B—C4B—C6B | −176.8 (2) |
C14A—N1A—C5A—O2A | 3.9 (3) | C1B—N1B—C5B—O2B | 178.1 (2) |
C1A—N1A—C5A—C4A | 3.4 (3) | C14B—N1B—C5B—O2B | −1.4 (3) |
C14A—N1A—C5A—C4A | −174.7 (2) | C1B—N1B—C5B—C4B | −2.2 (3) |
C3A—C4A—C5A—O2A | −179.6 (2) | C14B—N1B—C5B—C4B | 178.3 (2) |
C6A—C4A—C5A—O2A | −2.1 (4) | C3B—C4B—C5B—O2B | 179.0 (2) |
C3A—C4A—C5A—N1A | −1.1 (3) | C6B—C4B—C5B—O2B | −1.8 (4) |
C6A—C4A—C5A—N1A | 176.44 (19) | C3B—C4B—C5B—N1B | −0.7 (3) |
C7A—N2A—C6A—O3A | 0.7 (4) | C6B—C4B—C5B—N1B | 178.46 (19) |
C7A—N2A—C6A—C4A | −178.2 (2) | C7B—N2B—C6B—O3B | −1.2 (4) |
C3A—C4A—C6A—O3A | −3.1 (3) | C7B—N2B—C6B—C4B | 179.1 (2) |
C5A—C4A—C6A—O3A | 179.3 (2) | C3B—C4B—C6B—O3B | −5.5 (3) |
C3A—C4A—C6A—N2A | 175.7 (2) | C5B—C4B—C6B—O3B | 175.4 (2) |
C5A—C4A—C6A—N2A | −1.9 (3) | C3B—C4B—C6B—N2B | 174.2 (2) |
C13A—N4A—C7A—N3A | 0.3 (3) | C5B—C4B—C6B—N2B | −5.0 (3) |
C13A—N4A—C7A—N2A | 179.0 (2) | C13B—N4B—C7B—N3B | −1.2 (3) |
C8A—N3A—C7A—N4A | −0.3 (3) | C13B—N4B—C7B—N2B | 178.3 (2) |
C8A—N3A—C7A—N2A | −179.0 (2) | C8B—N3B—C7B—N4B | 1.2 (3) |
C6A—N2A—C7A—N4A | −177.6 (2) | C8B—N3B—C7B—N2B | −178.3 (2) |
C6A—N2A—C7A—N3A | 1.0 (4) | C6B—N2B—C7B—N4B | −177.0 (2) |
C7A—N3A—C8A—C13A | 0.2 (2) | C6B—N2B—C7B—N3B | 2.4 (4) |
C7A—N3A—C8A—C9A | 178.7 (3) | C7B—N3B—C8B—C9B | 178.3 (3) |
C13A—C8A—C9A—C10A | 0.3 (4) | C7B—N3B—C8B—C13B | −0.7 (2) |
N3A—C8A—C9A—C10A | −178.0 (2) | C13B—C8B—C9B—C10B | −0.4 (4) |
C8A—C9A—C10A—C11A | −0.5 (4) | N3B—C8B—C9B—C10B | −179.3 (2) |
C9A—C10A—C11A—C12A | 0.0 (4) | C8B—C9B—C10B—C11B | −0.2 (4) |
C10A—C11A—C12A—C13A | 0.6 (4) | C9B—C10B—C11B—C12B | −0.3 (4) |
N3A—C8A—C13A—N4A | 0.0 (3) | C10B—C11B—C12B—C13B | 1.3 (4) |
C9A—C8A—C13A—N4A | −178.7 (2) | C9B—C8B—C13B—C12B | 1.5 (4) |
N3A—C8A—C13A—C12A | 178.9 (2) | N3B—C8B—C13B—C12B | −179.4 (2) |
C9A—C8A—C13A—C12A | 0.2 (4) | C9B—C8B—C13B—N4B | −179.1 (2) |
C7A—N4A—C13A—C8A | −0.2 (3) | N3B—C8B—C13B—N4B | 0.0 (3) |
C7A—N4A—C13A—C12A | −179.0 (2) | C11B—C12B—C13B—C8B | −1.9 (4) |
C11A—C12A—C13A—C8A | −0.7 (4) | C11B—C12B—C13B—N4B | 178.8 (2) |
C11A—C12A—C13A—N4A | 178.0 (2) | C7B—N4B—C13B—C8B | 0.7 (3) |
C1A—N1A—C14A—C15A | 97.7 (3) | C7B—N4B—C13B—C12B | 180.0 (2) |
C5A—N1A—C14A—C15A | −84.2 (3) | C1B—N1B—C14B—C15B | −94.4 (3) |
N1A—C14A—C15A—C16A | 174.8 (3) | C5B—N1B—C14B—C15B | 85.0 (3) |
C18A—O5A—C17A—O4A | 6.0 (5) | N1B—C14B—C15B—C16B | −177.3 (3) |
C18A—O5A—C17A—C2A | −174.9 (3) | C18B—O5B—C17B—O4B | 7.1 (5) |
C1A—C2A—C17A—O4A | 47.2 (4) | C18B—O5B—C17B—C2B | −172.5 (3) |
C3A—C2A—C17A—O4A | −130.0 (3) | C1B—C2B—C17B—O4B | 59.4 (4) |
C1A—C2A—C17A—O5A | −131.9 (3) | C3B—C2B—C17B—O4B | −117.4 (4) |
C3A—C2A—C17A—O5A | 50.9 (3) | C1B—C2B—C17B—O5B | −121.0 (3) |
C17A—O5A—C18A—C19A | 175.1 (5) | C3B—C2B—C17B—O5B | 62.3 (3) |
C17A—O5A—C18A—C19D | 92.5 (11) | C17B—O5B—C18B—C19B | 84.1 (4) |
Symmetry code: (i) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O3A | 0.82 | 1.77 | 2.503 (2) | 149 |
O1B—H1B···O3B | 0.82 | 1.78 | 2.508 (2) | 148 |
N2A—H2A···O2A | 0.86 | 1.88 | 2.600 (3) | 140 |
N2B—H2B···O2B | 0.86 | 1.88 | 2.596 (3) | 139 |
N3A—H3A···O2ii | 0.86 | 2.34 | 2.968 (3) | 130 |
N3A—H3A···O3A | 0.86 | 2.21 | 2.710 (3) | 117 |
N3B—H3B···O1iii | 0.86 | 2.46 | 3.106 (6) | 132 |
N3B—H3B···O3B | 0.86 | 2.18 | 2.691 (3) | 118 |
O2—H2···N4A | 0.82 | 2.27 | 2.926 (3) | 138 |
O1—H1···N4B | 0.82 | 2.35 | 3.050 (6) | 144 |
Symmetry codes: (ii) −x+2, −y+1, −z; (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | 4C20H22N4O5·2C2H6O·CH4O |
Mr | 1717.84 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.5527 (4), 13.9720 (4), 16.0242 (5) |
α, β, γ (°) | 86.804 (3), 70.980 (3), 78.652 (3) |
V (Å3) | 2189.90 (12) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur3 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23866, 7499, 3785 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.170, 0.89 |
No. of reflections | 7499 |
No. of parameters | 596 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.35 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXTL (Sheldrick, 2008), XP (Bruker, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O3A | 0.82 | 1.77 | 2.503 (2) | 148.5 |
O1B—H1B···O3B | 0.82 | 1.78 | 2.508 (2) | 147.9 |
N2A—H2A···O2A | 0.86 | 1.88 | 2.600 (3) | 139.6 |
N2B—H2B···O2B | 0.86 | 1.88 | 2.596 (3) | 139.0 |
N3A—H3A···O2i | 0.86 | 2.34 | 2.968 (3) | 129.7 |
N3A—H3A···O3A | 0.86 | 2.21 | 2.710 (3) | 116.6 |
N3B—H3B···O1ii | 0.86 | 2.46 | 3.106 (6) | 132.4 |
N3B—H3B···O3B | 0.86 | 2.18 | 2.691 (3) | 117.8 |
O2—H2···N4A | 0.82 | 2.27 | 2.926 (3) | 137.5 |
O1—H1···N4B | 0.82 | 2.35 | 3.050 (6) | 144.2 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z+1. |
References
Bruker (1998). XP. Bruker AXS Inc., Karlsruhe, Germany. Google Scholar
Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767–784. Weinheim: VCH. Google Scholar
Low, J. N. & Wilson, C. C. (1983). Acta Cryst. C39, 1688–1690. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ukrainets, I. V., Bezugly, P. A., Gorokhova, O. V., Treskach, V. I. & Turov, A. V. (1993). Khim. Geterotsikl. Soedin. pp. 105–108. Google Scholar
Ukrainets, I. V., Sidorenko, L. V., Gorokhova, O. V. & Shishkin, O. V. (2006). Khim. Geterotsikl. Soedin. pp. 217–223. Google Scholar
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.
N-acylic derivatives of 2-aminobenzoimidazole are considered as potential antithyroid drugs (Ukrainets et al., 1993), for what the structures of these compounds are of particular interest. In the present paper, we report the crystal structure of ethyl-5(1H- benzoimidazol-2-ylcarbamoyl)-4-hydroxy-2-methyl-6-oxo-1-propyl-1,6- dihydropyridine-3-carboxylate (I). The compound exists as a ethanol:methanol solvate in a 4:2:1 ratio. The asymmetric unit contains two molecules (A and B) of I, one ethanol molecule and one methanol molecule located in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in molecules A and B lie in a plane within 0.03 Å due to the formation of many O—H···O, N—H···O intramolecular hydrogen bonds (Table 1, top eight entries). The formation of these hydrogen bonds causes also the redistribution of the electron density within the hydroxypyridone fragment. The O2—C5, O3—C6 and C3—C4 bonds (See Supplementary Material) are elongated as compared with reported value (mean values in the literature: 1.210 Å for the C=O and 1.326 Å for the C—C bond; Bürgi & Dunitz, 1994) and the O1—C3 and C4—C5 bonds are, instead, shorter (mean values in the literature: 1.362 Å and 1.455 Å). Some elongation of the C1—C2 bond and shortening of the C2—C3 bond can be caused, probably, by the strong conjugation between endocyclic double bonds which is typical for the pyridinone ring (Low & Wilson, 1983). The substituent at the C2 atom is turned relatively to the plane of the heterocycle (C1—C2—C17—O4 torsion angle: 47.2 (4) ° in A and 59.3 (4) ° in B). The ethyl group has sp-conformation relatively to the C17—O4 bond (C18—O5—C17—O4 torsion angle: 6.0 (5) Å (A) 7.3 (5) Å (B)). In molecule B the ethyl group is orthogonal to the C17—O5 bond (C17—O5—C18—C19 torsion angle: 84.0 (4) °) while in the molecule A this group is disordered over three positions due to the rotation around the O5—C18 bond with populations 0.50:0.25:0.25 and C17—O5—C18—C19 torsion angle: 175.0 (5) °, 139.3 (9) %A and 92 (1) °, respectively. In the crystal phase the molecules of I form layers parallel to (010). Neighbouring layers are interlinked through H-bonds mediated by the bridging solvate molecules (Table 1, last two entries).