organic compounds
4-N-Acetylamino-5-[N-acetyl-N-(tetra-O-acetyl-β-D-glucopyranosyl)amino]-1,3-dimethyluracil
aDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk
The title compound, C24H32N4O13, crystallizes with two molecules in the These have very similar conformations, and each contains an intramolecular N—H⋯O hydrogen bond. There are no significant intermolecular interactions.
Comment
The title compound, (I), has been prepared for use as an intermediate in the synthesis of nucleoside analogues with potential antitumour or antiviral applications.
Compound (I) crystallizes with two independent molecules (Fig. 1) in the P21, and the two molecules have very similar conformations. In the glucopyranose rings, the ring-puckering parameters (Cremer & Pople, 1975) in molecules 1 and 2 (containing N11 and N31 respectively, Fig. 1) are, for the atom sequences (O25, C21–C25) and (O45, C41–C45), θ = 3.5 (2) and 4.5 (2)°, respectively, and φ = 104 (4) and 342 (3)°, respectively: thus each ring has an almost perfect chair conformation, for which the ideal value of θ is zero.
The conformation adopted by all the substituents exocyclic to these chair rings are again similar for the two molecules, as shown by the leading torsion angles (Table 1), but the differences between them are sufficient to preclude any additional symmetry. The bond distances within the uracil rings are also very similar for the two molecules.
In each molecule there is a single intramolecular N—H⋯O hydrogen bond (Table 2), forming an S(7) motif (Bernstein et al., 1995), and these interactions may have an influence on the overall molecular conformations.
There are no significant direction-specific intermolecular interactions.
Experimental
Crystals of compound (I) were prepared according to a published procedure (Melgarejo Sampedro et al., 1982).
Crystal data
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Refinement
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All H atoms were located in difference maps, and then treated as riding atoms with distances C—H = 0.98 (CH3), 0.99 (CH2) or 1.00 Å (CH), and N—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C). In the absence of significant the Flack (1983) parameter was indeterminate (Flack & Bernardinelli, 2000); hence, the Friedel equivalents were merged prior to the final refinements. The was assigned by reference to the known configuration of the chiral starting material. There is evidence for considerable libration of the acetyl groups bonded to O26 and O46.
Data collection: COLLECT (Hooft, 1999); cell DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
Supporting information
https://doi.org/10.1107/S1600536806004223/lh6596sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806004223/lh6596Isup2.hkl
Data collection: COLLECT (Hooft, 1999); cell
DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).C24H32N4O13 | F(000) = 1232 |
Mr = 584.54 | Dx = 1.383 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 6642 reflections |
a = 8.8490 (1) Å | θ = 2.9–27.5° |
b = 17.8429 (2) Å | µ = 0.11 mm−1 |
c = 18.3058 (2) Å | T = 120 K |
β = 103.7830 (8)° | Block, colourless |
V = 2807.11 (6) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Bruker–Nonius KappaCCD diffractometer | 6642 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 5791 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
φ and ω scans | h = −11→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −22→23 |
Tmin = 0.954, Tmax = 0.980 | l = −23→23 |
46614 measured 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0458P)2 + 0.4658P] where P = (Fo2 + 2Fc2)/3 |
6642 reflections | (Δ/σ)max < 0.001 |
755 parameters | Δρmax = 0.25 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
x | y | z | Uiso*/Ueq | ||
N11 | 0.9337 (2) | 0.42742 (12) | 0.83728 (10) | 0.0222 (4) | |
C11 | 0.8141 (3) | 0.38198 (16) | 0.85942 (15) | 0.0339 (6) | |
C12 | 1.0086 (2) | 0.48112 (14) | 0.88748 (12) | 0.0225 (5) | |
O12 | 0.96987 (19) | 0.49537 (11) | 0.94561 (9) | 0.0310 (4) | |
N13 | 1.1308 (2) | 0.51828 (11) | 0.86795 (10) | 0.0221 (4) | |
C13 | 1.1979 (3) | 0.58236 (15) | 0.91553 (14) | 0.0294 (5) | |
C14 | 1.1807 (2) | 0.50003 (13) | 0.80455 (12) | 0.0201 (4) | |
N14 | 1.3161 (2) | 0.53533 (11) | 0.79646 (11) | 0.0230 (4) | |
C141 | 1.4590 (3) | 0.52158 (14) | 0.84579 (13) | 0.0238 (5) | |
O141 | 1.47059 (19) | 0.48102 (11) | 0.89996 (9) | 0.0308 (4) | |
C142 | 1.5929 (3) | 0.56229 (16) | 0.82671 (15) | 0.0307 (5) | |
C15 | 1.0978 (2) | 0.45189 (12) | 0.75244 (12) | 0.0190 (4) | |
N15 | 1.1450 (2) | 0.43373 (10) | 0.68527 (10) | 0.0185 (4) | |
C151 | 1.2325 (3) | 0.37007 (13) | 0.67975 (13) | 0.0238 (5) | |
O151 | 1.2766 (2) | 0.35754 (10) | 0.62307 (10) | 0.0310 (4) | |
C152 | 1.2678 (3) | 0.31951 (16) | 0.74688 (17) | 0.0383 (7) | |
C21 | 1.1210 (2) | 0.48574 (12) | 0.62313 (12) | 0.0190 (4) | |
C22 | 0.9712 (2) | 0.53131 (12) | 0.61122 (11) | 0.0183 (4) | |
O22 | 0.84262 (17) | 0.47985 (9) | 0.59061 (8) | 0.0210 (3) | |
C221 | 0.7297 (3) | 0.48458 (14) | 0.62960 (13) | 0.0246 (5) | |
O221 | 0.7331 (2) | 0.53006 (11) | 0.67844 (10) | 0.0335 (4) | |
C222 | 0.6069 (3) | 0.42667 (17) | 0.60451 (15) | 0.0356 (6) | |
C23 | 0.9632 (3) | 0.58685 (13) | 0.54700 (12) | 0.0202 (4) | |
O23 | 0.82640 (17) | 0.63257 (9) | 0.54400 (8) | 0.0209 (3) | |
C231 | 0.7520 (3) | 0.66120 (13) | 0.47597 (12) | 0.0227 (5) | |
O231 | 0.7882 (2) | 0.64737 (11) | 0.41852 (9) | 0.0351 (4) | |
C232 | 0.6224 (3) | 0.71199 (16) | 0.48277 (14) | 0.0309 (5) | |
C24 | 1.1071 (3) | 0.63619 (13) | 0.56516 (12) | 0.0211 (4) | |
O24 | 1.1150 (2) | 0.68135 (9) | 0.50130 (9) | 0.0276 (4) | |
C241 | 1.0788 (3) | 0.75487 (14) | 0.50305 (16) | 0.0316 (6) | |
O241 | 1.0356 (3) | 0.78322 (11) | 0.55370 (13) | 0.0471 (5) | |
C242 | 1.0978 (4) | 0.79121 (19) | 0.4323 (2) | 0.0530 (9) | |
C25 | 1.2550 (3) | 0.58918 (14) | 0.58160 (14) | 0.0254 (5) | |
C26 | 1.3980 (3) | 0.63618 (16) | 0.60911 (17) | 0.0363 (6) | |
O26 | 1.3865 (2) | 0.67209 (11) | 0.67852 (12) | 0.0399 (5) | |
C261 | 1.4265 (3) | 0.74464 (17) | 0.6863 (2) | 0.0535 (9) | |
O261 | 1.4703 (3) | 0.77954 (14) | 0.6391 (2) | 0.0902 (11) | |
C262 | 1.4111 (4) | 0.7743 (2) | 0.7600 (3) | 0.0689 (12) | |
O25 | 1.25068 (17) | 0.53662 (9) | 0.63982 (9) | 0.0223 (3) | |
C16 | 0.9674 (2) | 0.41112 (13) | 0.76804 (12) | 0.0200 (4) | |
O16 | 0.89333 (18) | 0.36325 (9) | 0.72684 (9) | 0.0256 (3) | |
N31 | 0.7874 (2) | 0.58238 (13) | 0.27061 (12) | 0.0281 (4) | |
C31 | 0.9234 (3) | 0.61973 (18) | 0.25399 (18) | 0.0394 (7) | |
C32 | 0.8188 (3) | 0.52956 (15) | 0.32636 (14) | 0.0301 (5) | |
O32 | 0.9519 (2) | 0.51303 (12) | 0.35935 (12) | 0.0414 (5) | |
N33 | 0.6916 (2) | 0.49383 (12) | 0.34391 (11) | 0.0258 (4) | |
C33 | 0.7291 (3) | 0.43388 (16) | 0.40016 (14) | 0.0348 (6) | |
C34 | 0.5417 (2) | 0.51248 (13) | 0.30817 (12) | 0.0215 (4) | |
N34 | 0.4231 (2) | 0.47380 (11) | 0.33021 (10) | 0.0232 (4) | |
C341 | 0.3989 (3) | 0.47838 (14) | 0.40223 (13) | 0.0260 (5) | |
O341 | 0.4779 (2) | 0.51943 (11) | 0.44949 (9) | 0.0341 (4) | |
C342 | 0.2728 (3) | 0.42821 (16) | 0.41584 (14) | 0.0330 (6) | |
C35 | 0.5133 (2) | 0.56315 (12) | 0.25089 (12) | 0.0202 (4) | |
N35 | 0.3594 (2) | 0.57824 (11) | 0.20807 (10) | 0.0197 (4) | |
C351 | 0.2876 (3) | 0.64703 (13) | 0.21261 (13) | 0.0234 (5) | |
O351 | 0.1687 (2) | 0.66401 (10) | 0.16741 (10) | 0.0317 (4) | |
C352 | 0.3607 (3) | 0.69583 (15) | 0.27864 (16) | 0.0345 (6) | |
C41 | 0.2791 (2) | 0.52555 (13) | 0.15225 (12) | 0.0197 (4) | |
C42 | 0.3861 (2) | 0.47726 (13) | 0.11738 (12) | 0.0198 (4) | |
O42 | 0.46192 (17) | 0.52602 (9) | 0.07462 (8) | 0.0230 (3) | |
C421 | 0.6186 (3) | 0.51840 (16) | 0.08439 (14) | 0.0308 (6) | |
O421 | 0.6951 (2) | 0.47453 (13) | 0.12746 (11) | 0.0405 (5) | |
C422 | 0.6813 (3) | 0.5733 (2) | 0.03738 (16) | 0.0430 (7) | |
C43 | 0.2922 (2) | 0.41926 (13) | 0.06475 (12) | 0.0205 (4) | |
O43 | 0.40424 (18) | 0.37114 (10) | 0.04277 (9) | 0.0241 (3) | |
C431 | 0.3674 (3) | 0.34180 (14) | −0.02775 (13) | 0.0267 (5) | |
O431 | 0.2442 (2) | 0.35106 (10) | −0.07145 (9) | 0.0313 (4) | |
C432 | 0.5003 (3) | 0.29657 (17) | −0.04135 (16) | 0.0381 (6) | |
C44 | 0.1912 (2) | 0.37420 (13) | 0.10573 (12) | 0.0208 (4) | |
O44 | 0.08784 (18) | 0.32624 (9) | 0.05350 (9) | 0.0238 (3) | |
C441 | 0.1278 (3) | 0.25301 (14) | 0.05120 (14) | 0.0268 (5) | |
O441 | 0.2397 (2) | 0.22611 (11) | 0.09376 (12) | 0.0431 (5) | |
C442 | 0.0179 (3) | 0.21355 (16) | −0.01072 (15) | 0.0343 (6) | |
C45 | 0.0903 (2) | 0.42695 (13) | 0.13932 (12) | 0.0210 (4) | |
C46 | −0.0091 (3) | 0.38646 (14) | 0.18349 (14) | 0.0269 (5) | |
O46 | 0.0868 (2) | 0.33473 (10) | 0.23564 (9) | 0.0303 (4) | |
C461 | 0.0440 (3) | 0.26187 (16) | 0.23186 (16) | 0.0362 (6) | |
O461 | −0.0687 (3) | 0.23867 (12) | 0.18726 (14) | 0.0560 (6) | |
C462 | 0.1527 (4) | 0.2170 (2) | 0.2892 (2) | 0.0630 (10) | |
O45 | 0.19311 (17) | 0.47638 (9) | 0.19027 (8) | 0.0208 (3) | |
C36 | 0.6397 (3) | 0.60310 (13) | 0.23045 (12) | 0.0231 (5) | |
O36 | 0.6200 (2) | 0.65264 (10) | 0.18299 (9) | 0.0288 (4) | |
H11A | 0.8177 | 0.3906 | 0.9127 | 0.051* | |
H11B | 0.8332 | 0.3288 | 0.8515 | 0.051* | |
H11C | 0.7114 | 0.3961 | 0.8289 | 0.051* | |
H13A | 1.2222 | 0.6227 | 0.8838 | 0.044* | |
H13B | 1.2934 | 0.5665 | 0.9514 | 0.044* | |
H13C | 1.1229 | 0.6005 | 0.9431 | 0.044* | |
H14 | 1.3170 | 0.5518 | 0.7513 | 0.028* | |
H14A | 1.6909 | 0.5433 | 0.8582 | 0.046* | |
H14B | 1.5840 | 0.6160 | 0.8359 | 0.046* | |
H14C | 1.5913 | 0.5541 | 0.7736 | 0.046* | |
H15A | 1.3369 | 0.3454 | 0.7891 | 0.057* | |
H15B | 1.3188 | 0.2739 | 0.7349 | 0.057* | |
H15C | 1.1708 | 0.3061 | 0.7606 | 0.057* | |
H21 | 1.1220 | 0.4577 | 0.5759 | 0.023* | |
H22 | 0.9669 | 0.5585 | 0.6584 | 0.022* | |
H22A | 0.5070 | 0.4459 | 0.6106 | 0.053* | |
H22B | 0.6344 | 0.3813 | 0.6350 | 0.053* | |
H22C | 0.5987 | 0.4147 | 0.5515 | 0.053* | |
H23 | 0.9550 | 0.5599 | 0.4983 | 0.024* | |
H23A | 0.5233 | 0.6851 | 0.4677 | 0.046* | |
H23B | 0.6206 | 0.7556 | 0.4501 | 0.046* | |
H23C | 0.6381 | 0.7287 | 0.5351 | 0.046* | |
H24 | 1.1052 | 0.6690 | 0.6092 | 0.025* | |
H24A | 1.0866 | 0.8456 | 0.4362 | 0.080* | |
H24B | 1.0181 | 0.7723 | 0.3896 | 0.080* | |
H24C | 1.2013 | 0.7796 | 0.4248 | 0.080* | |
H25 | 1.2631 | 0.5617 | 0.5351 | 0.030* | |
H26A | 1.4922 | 0.6043 | 0.6180 | 0.044* | |
H26B | 1.4057 | 0.6745 | 0.5710 | 0.044* | |
H26C | 1.3990 | 0.8289 | 0.7569 | 0.103* | |
H26D | 1.5045 | 0.7616 | 0.7989 | 0.103* | |
H26E | 1.3197 | 0.7519 | 0.7729 | 0.103* | |
H31A | 0.8885 | 0.6570 | 0.2143 | 0.059* | |
H31B | 0.9891 | 0.5824 | 0.2372 | 0.059* | |
H31C | 0.9832 | 0.6446 | 0.2995 | 0.059* | |
H33A | 0.6442 | 0.3973 | 0.3913 | 0.052* | |
H33B | 0.7426 | 0.4553 | 0.4506 | 0.052* | |
H33C | 0.8256 | 0.4090 | 0.3962 | 0.052* | |
H34 | 0.3436 | 0.4602 | 0.2938 | 0.028* | |
H34A | 0.2798 | 0.4250 | 0.4700 | 0.050* | |
H34B | 0.2849 | 0.3781 | 0.3961 | 0.050* | |
H34C | 0.1712 | 0.4487 | 0.3903 | 0.050* | |
H35A | 0.2964 | 0.7406 | 0.2787 | 0.052* | |
H35B | 0.4650 | 0.7109 | 0.2749 | 0.052* | |
H35C | 0.3681 | 0.6678 | 0.3254 | 0.052* | |
H41 | 0.2047 | 0.5533 | 0.1115 | 0.024* | |
H42 | 0.4655 | 0.4518 | 0.1579 | 0.024* | |
H42A | 0.7429 | 0.5467 | 0.0077 | 0.065* | |
H42B | 0.7474 | 0.6099 | 0.0701 | 0.065* | |
H42C | 0.5948 | 0.5994 | 0.0035 | 0.065* | |
H43 | 0.2256 | 0.4444 | 0.0195 | 0.025* | |
H43A | 0.5783 | 0.3301 | −0.0537 | 0.057* | |
H43B | 0.4623 | 0.2620 | −0.0833 | 0.057* | |
H43C | 0.5475 | 0.2679 | 0.0040 | 0.057* | |
H44 | 0.2586 | 0.3434 | 0.1464 | 0.025* | |
H44A | 0.0343 | 0.1593 | −0.0050 | 0.051* | |
H44B | 0.0359 | 0.2297 | −0.0591 | 0.051* | |
H44C | −0.0892 | 0.2256 | −0.0089 | 0.051* | |
H45 | 0.0221 | 0.4570 | 0.0983 | 0.025* | |
H46A | −0.0574 | 0.4232 | 0.2115 | 0.032* | |
H46B | −0.0932 | 0.3587 | 0.1487 | 0.032* | |
H46C | 0.1498 | 0.1646 | 0.2727 | 0.095* | |
H46D | 0.1219 | 0.2199 | 0.3371 | 0.095* | |
H46E | 0.2585 | 0.2367 | 0.2957 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0198 (9) | 0.0288 (10) | 0.0191 (9) | 0.0010 (8) | 0.0065 (7) | 0.0038 (8) |
C11 | 0.0324 (13) | 0.0385 (15) | 0.0363 (14) | −0.0042 (12) | 0.0191 (11) | 0.0055 (12) |
C12 | 0.0204 (10) | 0.0279 (12) | 0.0197 (10) | 0.0061 (9) | 0.0056 (8) | 0.0028 (9) |
O12 | 0.0294 (9) | 0.0424 (11) | 0.0227 (8) | 0.0060 (8) | 0.0094 (7) | 0.0000 (7) |
N13 | 0.0214 (9) | 0.0252 (10) | 0.0196 (8) | 0.0030 (8) | 0.0049 (7) | −0.0017 (8) |
C13 | 0.0330 (13) | 0.0272 (13) | 0.0285 (12) | −0.0001 (11) | 0.0087 (10) | −0.0056 (10) |
C14 | 0.0204 (10) | 0.0189 (11) | 0.0213 (10) | 0.0029 (8) | 0.0053 (8) | 0.0028 (8) |
N14 | 0.0225 (9) | 0.0246 (10) | 0.0225 (9) | −0.0028 (8) | 0.0065 (7) | 0.0024 (8) |
C141 | 0.0238 (10) | 0.0222 (11) | 0.0262 (11) | −0.0005 (9) | 0.0072 (9) | −0.0056 (10) |
O141 | 0.0261 (8) | 0.0342 (10) | 0.0306 (9) | −0.0010 (8) | 0.0037 (7) | 0.0067 (8) |
C142 | 0.0260 (12) | 0.0341 (14) | 0.0338 (13) | −0.0020 (11) | 0.0105 (10) | −0.0003 (11) |
C15 | 0.0186 (10) | 0.0201 (11) | 0.0188 (10) | 0.0033 (8) | 0.0054 (8) | 0.0033 (8) |
N15 | 0.0222 (9) | 0.0158 (9) | 0.0189 (8) | 0.0023 (7) | 0.0075 (7) | 0.0020 (7) |
C151 | 0.0245 (11) | 0.0189 (11) | 0.0311 (12) | 0.0010 (9) | 0.0124 (9) | 0.0022 (9) |
O151 | 0.0367 (9) | 0.0242 (9) | 0.0385 (10) | 0.0059 (8) | 0.0214 (8) | 0.0011 (8) |
C152 | 0.0442 (15) | 0.0298 (14) | 0.0467 (16) | 0.0162 (12) | 0.0221 (13) | 0.0153 (12) |
C21 | 0.0223 (10) | 0.0171 (10) | 0.0190 (10) | −0.0006 (9) | 0.0079 (8) | 0.0013 (8) |
C22 | 0.0202 (10) | 0.0169 (11) | 0.0178 (9) | −0.0009 (8) | 0.0048 (8) | 0.0004 (8) |
O22 | 0.0218 (7) | 0.0201 (8) | 0.0210 (7) | −0.0037 (6) | 0.0051 (6) | 0.0012 (6) |
C221 | 0.0204 (10) | 0.0288 (13) | 0.0250 (11) | 0.0041 (9) | 0.0059 (9) | 0.0088 (10) |
O221 | 0.0314 (9) | 0.0349 (10) | 0.0395 (10) | 0.0028 (8) | 0.0190 (8) | 0.0008 (9) |
C222 | 0.0237 (12) | 0.0434 (16) | 0.0364 (14) | −0.0070 (11) | 0.0011 (10) | 0.0132 (12) |
C23 | 0.0242 (11) | 0.0181 (10) | 0.0192 (10) | 0.0018 (9) | 0.0071 (8) | 0.0008 (9) |
O23 | 0.0228 (7) | 0.0210 (8) | 0.0187 (7) | 0.0027 (6) | 0.0044 (6) | 0.0022 (6) |
C231 | 0.0270 (11) | 0.0170 (11) | 0.0214 (11) | −0.0030 (9) | 0.0002 (9) | 0.0027 (9) |
O231 | 0.0504 (11) | 0.0337 (10) | 0.0195 (8) | 0.0097 (9) | 0.0051 (8) | 0.0009 (7) |
C232 | 0.0283 (12) | 0.0347 (14) | 0.0296 (12) | 0.0053 (11) | 0.0071 (10) | 0.0105 (11) |
C24 | 0.0272 (11) | 0.0168 (11) | 0.0212 (10) | 0.0014 (9) | 0.0095 (9) | 0.0046 (9) |
O24 | 0.0358 (9) | 0.0216 (8) | 0.0277 (8) | 0.0004 (7) | 0.0123 (7) | 0.0083 (7) |
C241 | 0.0246 (12) | 0.0198 (12) | 0.0477 (16) | −0.0014 (10) | 0.0036 (11) | 0.0078 (11) |
O241 | 0.0585 (13) | 0.0217 (10) | 0.0628 (13) | 0.0037 (9) | 0.0181 (11) | 0.0002 (10) |
C242 | 0.0512 (18) | 0.0389 (17) | 0.073 (2) | 0.0054 (15) | 0.0228 (16) | 0.0313 (17) |
C25 | 0.0278 (12) | 0.0217 (12) | 0.0303 (12) | 0.0021 (9) | 0.0143 (10) | 0.0090 (10) |
C26 | 0.0249 (12) | 0.0330 (14) | 0.0540 (17) | 0.0003 (11) | 0.0153 (12) | 0.0174 (13) |
O26 | 0.0329 (10) | 0.0285 (10) | 0.0522 (12) | −0.0107 (8) | −0.0019 (9) | 0.0062 (9) |
C261 | 0.0239 (13) | 0.0250 (15) | 0.109 (3) | 0.0006 (12) | 0.0101 (16) | 0.0023 (18) |
O261 | 0.0767 (18) | 0.0241 (12) | 0.191 (3) | −0.0010 (12) | 0.073 (2) | 0.0165 (17) |
C262 | 0.0379 (17) | 0.045 (2) | 0.112 (3) | −0.0048 (15) | −0.0069 (19) | −0.020 (2) |
O25 | 0.0213 (7) | 0.0208 (8) | 0.0259 (8) | −0.0002 (6) | 0.0080 (6) | 0.0073 (7) |
C16 | 0.0186 (10) | 0.0198 (11) | 0.0210 (10) | 0.0028 (9) | 0.0034 (8) | 0.0054 (9) |
O16 | 0.0275 (8) | 0.0236 (9) | 0.0254 (8) | −0.0045 (7) | 0.0058 (7) | 0.0024 (7) |
N31 | 0.0203 (9) | 0.0318 (11) | 0.0322 (10) | −0.0026 (9) | 0.0063 (8) | −0.0091 (9) |
C31 | 0.0235 (12) | 0.0430 (16) | 0.0549 (17) | −0.0101 (12) | 0.0154 (12) | −0.0140 (14) |
C32 | 0.0247 (12) | 0.0291 (13) | 0.0343 (13) | 0.0048 (10) | 0.0028 (10) | −0.0119 (11) |
O32 | 0.0220 (8) | 0.0410 (11) | 0.0568 (12) | 0.0068 (8) | 0.0005 (8) | −0.0081 (10) |
N33 | 0.0237 (10) | 0.0252 (10) | 0.0246 (9) | 0.0021 (8) | −0.0020 (8) | −0.0033 (8) |
C33 | 0.0359 (14) | 0.0311 (14) | 0.0311 (13) | 0.0067 (11) | −0.0042 (11) | 0.0029 (11) |
C34 | 0.0221 (10) | 0.0201 (11) | 0.0200 (10) | 0.0014 (9) | 0.0003 (8) | −0.0051 (9) |
N34 | 0.0239 (9) | 0.0248 (10) | 0.0182 (9) | −0.0022 (8) | −0.0002 (7) | 0.0012 (8) |
C341 | 0.0274 (11) | 0.0242 (12) | 0.0244 (11) | 0.0062 (10) | 0.0023 (9) | 0.0039 (10) |
O341 | 0.0427 (10) | 0.0342 (10) | 0.0238 (8) | −0.0014 (9) | 0.0049 (7) | −0.0037 (8) |
C342 | 0.0338 (13) | 0.0368 (15) | 0.0287 (12) | −0.0002 (11) | 0.0080 (10) | 0.0050 (11) |
C35 | 0.0188 (10) | 0.0199 (11) | 0.0210 (10) | −0.0015 (9) | 0.0026 (8) | −0.0052 (9) |
N35 | 0.0195 (8) | 0.0187 (9) | 0.0194 (9) | 0.0000 (7) | 0.0014 (7) | −0.0017 (7) |
C351 | 0.0246 (11) | 0.0203 (11) | 0.0278 (11) | 0.0009 (9) | 0.0111 (9) | 0.0027 (9) |
O351 | 0.0300 (9) | 0.0290 (9) | 0.0345 (9) | 0.0103 (8) | 0.0045 (7) | 0.0023 (8) |
C352 | 0.0339 (13) | 0.0267 (13) | 0.0436 (15) | −0.0003 (11) | 0.0104 (12) | −0.0106 (11) |
C41 | 0.0199 (10) | 0.0195 (11) | 0.0191 (10) | −0.0016 (9) | 0.0034 (8) | 0.0013 (9) |
C42 | 0.0217 (10) | 0.0196 (11) | 0.0181 (10) | −0.0007 (9) | 0.0047 (8) | 0.0017 (9) |
O42 | 0.0218 (7) | 0.0267 (9) | 0.0213 (7) | −0.0036 (7) | 0.0066 (6) | 0.0003 (7) |
C421 | 0.0238 (11) | 0.0411 (15) | 0.0292 (12) | −0.0053 (11) | 0.0094 (10) | −0.0156 (12) |
O421 | 0.0231 (8) | 0.0505 (12) | 0.0469 (11) | 0.0029 (9) | 0.0061 (8) | −0.0090 (10) |
C422 | 0.0385 (15) | 0.060 (2) | 0.0354 (14) | −0.0221 (14) | 0.0191 (12) | −0.0139 (14) |
C43 | 0.0212 (10) | 0.0201 (11) | 0.0191 (10) | 0.0021 (9) | 0.0028 (8) | 0.0001 (9) |
O43 | 0.0256 (8) | 0.0252 (9) | 0.0217 (7) | 0.0024 (7) | 0.0060 (6) | −0.0028 (7) |
C431 | 0.0357 (13) | 0.0224 (12) | 0.0242 (11) | −0.0041 (10) | 0.0114 (10) | −0.0015 (9) |
O431 | 0.0372 (10) | 0.0328 (10) | 0.0234 (8) | −0.0057 (8) | 0.0064 (7) | −0.0040 (7) |
C432 | 0.0443 (15) | 0.0375 (15) | 0.0370 (14) | 0.0038 (13) | 0.0185 (12) | −0.0096 (12) |
C44 | 0.0218 (10) | 0.0193 (11) | 0.0191 (10) | −0.0022 (9) | 0.0007 (8) | −0.0010 (9) |
O44 | 0.0254 (8) | 0.0209 (8) | 0.0230 (8) | −0.0033 (7) | 0.0016 (6) | −0.0020 (6) |
C441 | 0.0327 (13) | 0.0197 (12) | 0.0287 (12) | −0.0023 (10) | 0.0089 (10) | −0.0006 (10) |
O441 | 0.0492 (12) | 0.0245 (10) | 0.0480 (11) | 0.0074 (9) | −0.0038 (9) | −0.0015 (9) |
C442 | 0.0391 (14) | 0.0262 (13) | 0.0376 (14) | −0.0090 (11) | 0.0091 (11) | −0.0087 (11) |
C45 | 0.0188 (10) | 0.0213 (11) | 0.0211 (10) | −0.0021 (9) | 0.0014 (8) | −0.0010 (9) |
C46 | 0.0237 (11) | 0.0282 (13) | 0.0290 (12) | −0.0030 (10) | 0.0067 (9) | 0.0000 (10) |
O46 | 0.0324 (9) | 0.0314 (10) | 0.0257 (8) | −0.0070 (8) | 0.0041 (7) | 0.0058 (7) |
C461 | 0.0409 (15) | 0.0307 (14) | 0.0413 (15) | −0.0063 (12) | 0.0183 (12) | 0.0046 (12) |
O461 | 0.0584 (14) | 0.0305 (11) | 0.0720 (15) | −0.0144 (11) | 0.0011 (12) | −0.0006 (11) |
C462 | 0.057 (2) | 0.056 (2) | 0.073 (2) | −0.0048 (18) | 0.0116 (18) | 0.040 (2) |
O45 | 0.0211 (7) | 0.0202 (8) | 0.0209 (7) | −0.0042 (6) | 0.0049 (6) | −0.0013 (6) |
C36 | 0.0235 (11) | 0.0236 (12) | 0.0223 (11) | −0.0033 (9) | 0.0055 (9) | −0.0094 (9) |
O36 | 0.0332 (9) | 0.0261 (9) | 0.0283 (8) | −0.0067 (7) | 0.0097 (7) | −0.0033 (7) |
N11—C12 | 1.382 (3) | N31—C32 | 1.368 (4) |
C12—N13 | 1.386 (3) | C32—N33 | 1.396 (3) |
N13—C14 | 1.376 (3) | N33—C34 | 1.374 (3) |
C14—C15 | 1.361 (3) | C34—C35 | 1.362 (3) |
C15—C16 | 1.449 (3) | C35—C36 | 1.448 (3) |
C16—N11 | 1.400 (3) | C36—N31 | 1.389 (3) |
N11—C11 | 1.465 (3) | N31—C31 | 1.469 (3) |
C11—H11A | 0.98 | C31—H31A | 0.98 |
C11—H11B | 0.98 | C31—H31B | 0.98 |
C11—H11C | 0.98 | C31—H31C | 0.98 |
C12—O12 | 1.220 (3) | C32—O32 | 1.225 (3) |
N13—C13 | 1.474 (3) | N33—C33 | 1.467 (3) |
C13—H13A | 0.98 | C33—H33A | 0.98 |
C13—H13B | 0.98 | C33—H33B | 0.98 |
C13—H13C | 0.98 | C33—H33C | 0.98 |
C14—N14 | 1.392 (3) | C34—N34 | 1.394 (3) |
N14—C141 | 1.389 (3) | N34—C341 | 1.387 (3) |
N14—H14 | 0.88 | N34—H34 | 0.8799 |
C141—O141 | 1.212 (3) | C341—O341 | 1.219 (3) |
C141—C142 | 1.500 (3) | C341—C342 | 1.497 (4) |
C142—H14A | 0.98 | C342—H34A | 0.98 |
C142—H14B | 0.98 | C342—H34B | 0.98 |
C142—H14C | 0.98 | C342—H34C | 0.98 |
C15—N15 | 1.427 (3) | C35—N35 | 1.426 (3) |
N15—C151 | 1.392 (3) | N35—C351 | 1.394 (3) |
N15—C21 | 1.444 (3) | N35—C41 | 1.445 (3) |
C151—O151 | 1.213 (3) | C351—O351 | 1.212 (3) |
C151—C152 | 1.496 (3) | C351—C352 | 1.505 (3) |
C152—H15A | 0.98 | C352—H35A | 0.98 |
C152—H15B | 0.98 | C352—H35B | 0.98 |
C152—H15C | 0.98 | C352—H35C | 0.98 |
C21—O25 | 1.438 (3) | C41—O45 | 1.444 (3) |
C21—C22 | 1.526 (3) | C41—C42 | 1.528 (3) |
C21—H21 | 1.00 | C41—H41 | 1.00 |
C22—O22 | 1.441 (3) | C42—O42 | 1.439 (3) |
C22—C23 | 1.526 (3) | C42—C43 | 1.520 (3) |
C22—H22 | 1.00 | C42—H42 | 1.00 |
O22—C221 | 1.362 (3) | O42—C421 | 1.362 (3) |
C221—O221 | 1.202 (3) | C421—O421 | 1.199 (3) |
C221—C222 | 1.491 (4) | C421—C422 | 1.496 (4) |
C222—H22A | 0.98 | C422—H42A | 0.98 |
C222—H22B | 0.98 | C422—H42B | 0.98 |
C222—H22C | 0.98 | C422—H42C | 0.98 |
C23—O23 | 1.450 (3) | C43—O43 | 1.440 (3) |
C23—C24 | 1.518 (3) | C43—C44 | 1.525 (3) |
C23—H23 | 1.00 | C43—H43 | 1.00 |
O23—C231 | 1.362 (3) | O43—C431 | 1.359 (3) |
C231—O231 | 1.196 (3) | C431—O431 | 1.201 (3) |
C231—C232 | 1.490 (3) | C431—C432 | 1.495 (4) |
C232—H23A | 0.98 | C432—H43A | 0.98 |
C232—H23B | 0.98 | C432—H43B | 0.98 |
C232—H23C | 0.98 | C432—H43C | 0.98 |
C24—O24 | 1.435 (3) | C44—O44 | 1.438 (3) |
C24—C25 | 1.523 (3) | C44—C45 | 1.524 (3) |
C24—H24 | 1.00 | C44—H44 | 1.00 |
O24—C241 | 1.353 (3) | O44—C441 | 1.357 (3) |
C241—O241 | 1.196 (3) | C441—O441 | 1.205 (3) |
C241—C242 | 1.493 (4) | C441—C442 | 1.484 (4) |
C242—H24A | 0.98 | C442—H44A | 0.98 |
C242—H24B | 0.98 | C442—H44B | 0.98 |
C242—H24C | 0.98 | C442—H44C | 0.98 |
C25—O25 | 1.427 (3) | C45—O45 | 1.439 (3) |
C25—C26 | 1.501 (4) | C45—C46 | 1.512 (3) |
C25—H25 | 1.00 | C45—H45 | 1.00 |
C26—O26 | 1.448 (4) | C46—O46 | 1.448 (3) |
C26—H26A | 0.99 | C46—H46A | 0.99 |
C26—H26B | 0.99 | C46—H46B | 0.99 |
O26—C261 | 1.340 (4) | O46—C461 | 1.351 (3) |
C261—O261 | 1.203 (5) | C461—O461 | 1.202 (4) |
C261—C262 | 1.485 (6) | C461—C462 | 1.478 (4) |
C262—H26C | 0.98 | C462—H46C | 0.98 |
C262—H26D | 0.98 | C462—H46D | 0.98 |
C262—H26E | 0.98 | C462—H46E | 0.98 |
C16—O16 | 1.222 (3) | C36—O36 | 1.222 (3) |
C12—N11—C16 | 125.05 (19) | C32—N31—C36 | 125.2 (2) |
C12—N11—C11 | 117.59 (18) | C32—N31—C31 | 115.9 (2) |
C16—N11—C11 | 117.3 (2) | C36—N31—C31 | 118.9 (2) |
N11—C11—H11A | 109.5 | N31—C31—H31A | 109.5 |
N11—C11—H11B | 109.5 | N31—C31—H31B | 109.5 |
H11A—C11—H11B | 109.5 | H31A—C31—H31B | 109.5 |
N11—C11—H11C | 109.5 | N31—C31—H31C | 109.5 |
H11A—C11—H11C | 109.5 | H31A—C31—H31C | 109.5 |
H11B—C11—H11C | 109.5 | H31B—C31—H31C | 109.5 |
O12—C12—N11 | 122.3 (2) | O32—C32—N31 | 122.3 (2) |
O12—C12—N13 | 121.6 (2) | O32—C32—N33 | 120.7 (2) |
N11—C12—N13 | 116.10 (18) | N31—C32—N33 | 117.1 (2) |
C14—N13—C12 | 122.11 (19) | C34—N33—C32 | 121.4 (2) |
C14—N13—C13 | 121.10 (19) | C34—N33—C33 | 122.8 (2) |
C12—N13—C13 | 116.64 (18) | C32—N33—C33 | 115.8 (2) |
N13—C13—H13A | 109.5 | N33—C33—H33A | 109.5 |
N13—C13—H13B | 109.5 | N33—C33—H33B | 109.5 |
H13A—C13—H13B | 109.5 | H33A—C33—H33B | 109.5 |
N13—C13—H13C | 109.5 | N33—C33—H33C | 109.5 |
H13A—C13—H13C | 109.5 | H33A—C33—H33C | 109.5 |
H13B—C13—H13C | 109.5 | H33B—C33—H33C | 109.5 |
C15—C14—N13 | 120.84 (19) | C35—C34—N33 | 120.5 (2) |
C15—C14—N14 | 123.00 (19) | C35—C34—N34 | 122.57 (19) |
N13—C14—N14 | 116.12 (19) | N33—C34—N34 | 116.8 (2) |
C141—N14—C14 | 121.60 (19) | C341—N34—C34 | 122.88 (19) |
C141—N14—H14 | 117.4 | C341—N34—H34 | 117.4 |
C14—N14—H14 | 116.9 | C34—N34—H34 | 116.0 |
O141—C141—N14 | 121.6 (2) | O341—C341—N34 | 121.2 (2) |
O141—C141—C142 | 124.2 (2) | O341—C341—C342 | 124.4 (2) |
N14—C141—C142 | 114.2 (2) | N34—C341—C342 | 114.4 (2) |
C141—C142—H14A | 109.5 | C341—C342—H34A | 109.5 |
C141—C142—H14B | 109.5 | C341—C342—H34B | 109.5 |
H14A—C142—H14B | 109.5 | H34A—C342—H34B | 109.5 |
C141—C142—H14C | 109.5 | C341—C342—H34C | 109.5 |
H14A—C142—H14C | 109.5 | H34A—C342—H34C | 109.5 |
H14B—C142—H14C | 109.5 | H34B—C342—H34C | 109.5 |
C14—C15—N15 | 121.86 (19) | C34—C35—N35 | 121.69 (19) |
C14—C15—C16 | 120.02 (19) | C34—C35—C36 | 120.9 (2) |
N15—C15—C16 | 117.79 (19) | N35—C35—C36 | 117.39 (19) |
C151—N15—C15 | 122.01 (18) | C351—N35—C35 | 121.52 (18) |
C151—N15—C21 | 116.55 (17) | C351—N35—C41 | 117.44 (18) |
C15—N15—C21 | 120.98 (17) | C35—N35—C41 | 120.70 (18) |
O151—C151—N15 | 120.7 (2) | O351—C351—N35 | 120.9 (2) |
O151—C151—C152 | 123.0 (2) | O351—C351—C352 | 122.7 (2) |
N15—C151—C152 | 116.3 (2) | N35—C351—C352 | 116.3 (2) |
C151—C152—H15A | 109.5 | C351—C352—H35A | 109.5 |
C151—C152—H15B | 109.5 | C351—C352—H35B | 109.5 |
H15A—C152—H15B | 109.5 | H35A—C352—H35B | 109.5 |
C151—C152—H15C | 109.5 | C351—C352—H35C | 109.5 |
H15A—C152—H15C | 109.5 | H35A—C352—H35C | 109.5 |
H15B—C152—H15C | 109.5 | H35B—C352—H35C | 109.5 |
O25—C21—N15 | 106.16 (17) | O45—C41—N35 | 106.34 (16) |
O25—C21—C22 | 108.43 (17) | O45—C41—C42 | 107.99 (18) |
N15—C21—C22 | 114.49 (17) | N35—C41—C42 | 114.37 (17) |
O25—C21—H21 | 109.2 | O45—C41—H41 | 109.3 |
N15—C21—H21 | 109.2 | N35—C41—H41 | 109.3 |
C22—C21—H21 | 109.2 | C42—C41—H41 | 109.3 |
O22—C22—C21 | 107.64 (17) | O42—C42—C43 | 108.81 (16) |
O22—C22—C23 | 108.88 (16) | O42—C42—C41 | 107.58 (18) |
C21—C22—C23 | 109.58 (17) | C43—C42—C41 | 110.40 (17) |
O22—C22—H22 | 110.2 | O42—C42—H42 | 110.0 |
C21—C22—H22 | 110.2 | C43—C42—H42 | 110.0 |
C23—C22—H22 | 110.2 | C41—C42—H42 | 110.0 |
C221—O22—C22 | 117.10 (17) | C421—O42—C42 | 117.39 (19) |
O221—C221—O22 | 122.7 (2) | O421—C421—O42 | 123.3 (2) |
O221—C221—C222 | 125.7 (2) | O421—C421—C422 | 125.3 (2) |
O22—C221—C222 | 111.6 (2) | O42—C421—C422 | 111.4 (2) |
C221—C222—H22A | 109.5 | C421—C422—H42A | 109.5 |
C221—C222—H22B | 109.5 | C421—C422—H42B | 109.5 |
H22A—C222—H22B | 109.5 | H42A—C422—H42B | 109.5 |
C221—C222—H22C | 109.5 | C421—C422—H42C | 109.5 |
H22A—C222—H22C | 109.5 | H42A—C422—H42C | 109.5 |
H22B—C222—H22C | 109.5 | H42B—C422—H42C | 109.5 |
O23—C23—C24 | 109.34 (18) | O43—C43—C42 | 105.90 (17) |
O23—C23—C22 | 106.22 (16) | O43—C43—C44 | 110.25 (18) |
C24—C23—C22 | 108.99 (17) | C42—C43—C44 | 110.08 (17) |
O23—C23—H23 | 110.7 | O43—C43—H43 | 110.2 |
C24—C23—H23 | 110.7 | C42—C43—H43 | 110.2 |
C22—C23—H23 | 110.7 | C44—C43—H43 | 110.2 |
C231—O23—C23 | 117.58 (16) | C431—O43—C43 | 118.04 (17) |
O231—C231—O23 | 123.7 (2) | O431—C431—O43 | 123.7 (2) |
O231—C231—C232 | 124.9 (2) | O431—C431—C432 | 126.1 (2) |
O23—C231—C232 | 111.46 (19) | O43—C431—C432 | 110.2 (2) |
C231—C232—H23A | 109.5 | C431—C432—H43A | 109.5 |
C231—C232—H23B | 109.5 | C431—C432—H43B | 109.5 |
H23A—C232—H23B | 109.5 | H43A—C432—H43B | 109.5 |
C231—C232—H23C | 109.5 | C431—C432—H43C | 109.5 |
H23A—C232—H23C | 109.5 | H43A—C432—H43C | 109.5 |
H23B—C232—H23C | 109.5 | H43B—C432—H43C | 109.5 |
O24—C24—C23 | 110.38 (18) | O44—C44—C45 | 107.13 (17) |
O24—C24—C25 | 105.31 (17) | O44—C44—C43 | 109.95 (17) |
C23—C24—C25 | 111.12 (19) | C45—C44—C43 | 109.94 (19) |
O24—C24—H24 | 110.0 | O44—C44—H44 | 109.9 |
C23—C24—H24 | 110.0 | C45—C44—H44 | 109.9 |
C25—C24—H24 | 110.0 | C43—C44—H44 | 109.9 |
C241—O24—C24 | 117.9 (2) | C441—O44—C44 | 117.69 (18) |
O241—C241—O24 | 123.4 (2) | O441—C441—O44 | 122.9 (2) |
O241—C241—C242 | 127.7 (3) | O441—C441—C442 | 126.4 (2) |
O24—C241—C242 | 108.9 (2) | O44—C441—C442 | 110.6 (2) |
C241—C242—H24A | 109.5 | C441—C442—H44A | 109.5 |
C241—C242—H24B | 109.5 | C441—C442—H44B | 109.5 |
H24A—C242—H24B | 109.5 | H44A—C442—H44B | 109.5 |
C241—C242—H24C | 109.5 | C441—C442—H44C | 109.5 |
H24A—C242—H24C | 109.5 | H44A—C442—H44C | 109.5 |
H24B—C242—H24C | 109.5 | H44B—C442—H44C | 109.5 |
O25—C25—C26 | 106.7 (2) | O45—C45—C46 | 107.73 (18) |
O25—C25—C24 | 109.56 (17) | O45—C45—C44 | 107.40 (17) |
C26—C25—C24 | 112.0 (2) | C46—C45—C44 | 113.1 (2) |
O25—C25—H25 | 109.5 | O45—C45—H45 | 109.5 |
C26—C25—H25 | 109.5 | C46—C45—H45 | 109.5 |
C24—C25—H25 | 109.5 | C44—C45—H45 | 109.5 |
O26—C26—C25 | 108.2 (2) | O46—C46—C45 | 109.44 (18) |
O26—C26—H26A | 110.1 | O46—C46—H46A | 109.8 |
C25—C26—H26A | 110.1 | C45—C46—H46A | 109.8 |
O26—C26—H26B | 110.1 | O46—C46—H46B | 109.8 |
C25—C26—H26B | 110.1 | C45—C46—H46B | 109.8 |
H26A—C26—H26B | 108.4 | H46A—C46—H46B | 108.2 |
C261—O26—C26 | 116.7 (3) | C461—O46—C46 | 117.8 (2) |
O261—C261—O26 | 123.0 (4) | O461—C461—O46 | 122.9 (3) |
O261—C261—C262 | 125.7 (3) | O461—C461—C462 | 126.1 (3) |
O26—C261—C262 | 111.2 (3) | O46—C461—C462 | 111.0 (3) |
C261—C262—H26C | 109.5 | C461—C462—H46C | 109.5 |
C261—C262—H26D | 109.5 | C461—C462—H46D | 109.5 |
H26C—C262—H26D | 109.5 | H46C—C462—H46D | 109.5 |
C261—C262—H26E | 109.5 | C461—C462—H46E | 109.5 |
H26C—C262—H26E | 109.5 | H46C—C462—H46E | 109.5 |
H26D—C262—H26E | 109.5 | H46D—C462—H46E | 109.5 |
C25—O25—C21 | 114.74 (17) | C45—O45—C41 | 112.60 (15) |
O16—C16—N11 | 120.4 (2) | O36—C36—N31 | 121.7 (2) |
O16—C16—C15 | 124.4 (2) | O36—C36—C35 | 123.5 (2) |
N11—C16—C15 | 115.17 (19) | N31—C36—C35 | 114.8 (2) |
C16—N11—C12—O12 | 176.6 (2) | C36—N31—C32—O32 | 179.2 (2) |
C11—N11—C12—O12 | −5.9 (3) | C31—N31—C32—O32 | −1.6 (3) |
C16—N11—C12—N13 | −3.2 (3) | C36—N31—C32—N33 | 0.1 (3) |
C11—N11—C12—N13 | 174.2 (2) | C31—N31—C32—N33 | 179.3 (2) |
O12—C12—N13—C14 | 176.5 (2) | O32—C32—N33—C34 | 179.1 (2) |
N11—C12—N13—C14 | −3.6 (3) | N31—C32—N33—C34 | −1.8 (3) |
O12—C12—N13—C13 | −7.8 (3) | O32—C32—N33—C33 | −3.2 (3) |
N11—C12—N13—C13 | 172.08 (19) | N31—C32—N33—C33 | 175.9 (2) |
C12—N13—C14—C15 | 9.6 (3) | C32—N33—C34—C35 | 4.4 (3) |
C13—N13—C14—C15 | −165.9 (2) | C33—N33—C34—C35 | −173.1 (2) |
C12—N13—C14—N14 | −172.39 (19) | C32—N33—C34—N34 | −179.6 (2) |
C13—N13—C14—N14 | 12.1 (3) | C33—N33—C34—N34 | 2.9 (3) |
C15—C14—N14—C141 | −116.1 (2) | C35—C34—N34—C341 | −120.4 (2) |
N13—C14—N14—C141 | 65.9 (3) | N33—C34—N34—C341 | 63.6 (3) |
C14—N14—C141—O141 | −3.5 (3) | C34—N34—C341—O341 | 3.0 (3) |
C14—N14—C141—C142 | 177.8 (2) | C34—N34—C341—C342 | −175.8 (2) |
N13—C14—C15—N15 | 178.24 (19) | N33—C34—C35—N35 | 173.9 (2) |
N14—C14—C15—N15 | 0.3 (3) | N34—C34—C35—N35 | −1.9 (3) |
N13—C14—C15—C16 | −8.6 (3) | N33—C34—C35—C36 | −5.2 (3) |
N14—C14—C15—C16 | 173.5 (2) | N34—C34—C35—C36 | 179.0 (2) |
C14—C15—N15—C151 | 95.6 (3) | C34—C35—N35—C351 | 111.6 (2) |
C16—C15—N15—C151 | −77.7 (3) | C36—C35—N35—C351 | −69.3 (3) |
C14—C15—N15—C21 | −76.4 (3) | C34—C35—N35—C41 | −75.3 (3) |
C16—C15—N15—C21 | 110.3 (2) | C36—C35—N35—C41 | 103.8 (2) |
C15—N15—C151—O151 | −176.9 (2) | C35—N35—C351—O351 | 167.5 (2) |
C21—N15—C151—O151 | −4.7 (3) | C41—N35—C351—O351 | −5.8 (3) |
C15—N15—C151—C152 | 3.0 (3) | C35—N35—C351—C352 | −15.9 (3) |
C21—N15—C151—C152 | 175.3 (2) | C41—N35—C351—C352 | 170.74 (19) |
C151—N15—C21—O25 | −88.4 (2) | C351—N35—C41—O45 | −95.2 (2) |
C15—N15—C21—O25 | 83.9 (2) | C35—N35—C41—O45 | 91.4 (2) |
C15—N15—C21—C22 | −35.7 (3) | C35—N35—C41—C42 | −27.7 (3) |
C22—C21—N15—C151 | 151.98 (19) | C42—C41—N35—C351 | 145.74 (19) |
O25—C21—C22—O22 | 176.96 (15) | O45—C41—C42—O42 | 175.45 (15) |
N15—C21—C22—O22 | −64.7 (2) | N35—C41—C42—O42 | −66.4 (2) |
O25—C21—C22—C23 | 58.7 (2) | O45—C41—C42—C43 | 56.9 (2) |
N15—C21—C22—C23 | 177.02 (18) | N35—C41—C42—C43 | 175.01 (17) |
C21—C22—O22—C221 | 129.62 (18) | C43—C42—O42—C421 | −107.5 (2) |
C23—C22—O22—C221 | −111.7 (2) | C41—C42—O42—C421 | 132.84 (19) |
C22—O22—C221—O221 | 1.3 (3) | C42—O42—C421—O421 | −1.5 (3) |
C22—O22—C221—C222 | −178.03 (19) | C42—O42—C421—C422 | −179.14 (19) |
O22—C22—C23—O23 | 67.9 (2) | O42—C42—C43—O43 | 69.3 (2) |
C21—C22—C23—O23 | −174.63 (16) | C41—C42—C43—O43 | −172.81 (16) |
O22—C22—C23—C24 | −174.41 (17) | O42—C42—C43—C44 | −171.48 (17) |
C21—C22—C23—C24 | −56.9 (2) | C41—C42—C43—C44 | −53.6 (2) |
C24—C23—O23—C231 | 91.9 (2) | C42—C43—O43—C431 | −146.41 (19) |
C22—C23—O23—C231 | −150.68 (18) | C44—C43—O43—C431 | 94.5 (2) |
C23—O23—C231—O231 | 4.2 (3) | C43—O43—C431—O431 | −3.4 (3) |
C23—O23—C231—C232 | −175.15 (19) | C43—O43—C431—C432 | 177.3 (2) |
O23—C23—C24—O24 | −72.9 (2) | O43—C43—C44—O44 | −71.0 (2) |
C22—C23—C24—O24 | 171.37 (17) | C42—C43—C44—O44 | 172.54 (17) |
O23—C23—C24—C25 | 170.63 (17) | O43—C43—C44—C45 | 171.30 (16) |
C22—C23—C24—C25 | 54.9 (2) | C42—C43—C44—C45 | 54.8 (2) |
C23—C24—O24—C241 | 104.9 (2) | C45—C44—O44—C441 | −140.4 (2) |
C25—C24—O24—C241 | −135.0 (2) | C43—C44—O44—C441 | 100.1 (2) |
C24—O24—C241—O241 | −2.7 (4) | C44—O44—C441—O441 | 4.7 (3) |
C24—O24—C241—C242 | 178.8 (2) | C44—O44—C441—C442 | −174.13 (19) |
O24—C24—C25—O25 | −174.16 (18) | O44—C44—C45—O45 | −178.58 (16) |
C23—C24—C25—O25 | −54.6 (2) | C43—C44—C45—O45 | −59.1 (2) |
O24—C24—C25—C26 | 67.7 (2) | O44—C44—C45—C46 | 62.7 (2) |
C23—C24—C25—C26 | −172.82 (19) | C43—C44—C45—C46 | −177.84 (18) |
O25—C25—C26—O26 | −58.6 (2) | O45—C45—C46—O46 | −69.2 (2) |
C24—C25—C26—O26 | 61.3 (3) | C44—C45—C46—O46 | 49.3 (3) |
C25—C26—O26—C261 | −136.4 (2) | C45—C46—O46—C461 | −124.2 (2) |
C26—O26—C261—O261 | −0.2 (4) | C46—O46—C461—O461 | 0.3 (4) |
C26—O26—C261—C262 | −179.4 (2) | C46—O46—C461—C462 | −179.4 (2) |
C26—C25—O25—C21 | −179.44 (19) | C46—C45—O45—C41 | −172.08 (18) |
C24—C25—O25—C21 | 59.1 (2) | C44—C45—O45—C41 | 65.8 (2) |
N15—C21—O25—C25 | 175.11 (17) | N35—C41—O45—C45 | 172.14 (16) |
C22—C21—O25—C25 | −61.4 (2) | C42—C41—O45—C45 | −64.7 (2) |
C12—N11—C16—O16 | −179.0 (2) | C32—N31—C36—O36 | 177.5 (2) |
C11—N11—C16—O16 | 3.5 (3) | C31—N31—C36—O36 | −1.7 (3) |
C12—N11—C16—C15 | 3.9 (3) | C32—N31—C36—C35 | −0.8 (3) |
C11—N11—C16—C15 | −173.5 (2) | C31—N31—C36—C35 | −180.0 (2) |
C14—C15—C16—O16 | −174.9 (2) | C34—C35—C36—O36 | −174.9 (2) |
N15—C15—C16—O16 | −1.4 (3) | N35—C35—C36—O36 | 6.0 (3) |
C14—C15—C16—N11 | 2.1 (3) | C34—C35—C36—N31 | 3.4 (3) |
N15—C15—C16—N11 | 175.51 (18) | N35—C35—C36—N31 | −175.75 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O25 | 0.88 | 2.00 | 2.787 (3) | 148 |
N34—H34···O45 | 0.88 | 2.06 | 2.867 (2) | 152 |
Acknowledgements
X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. The authors thank the staff for all their help and advice. ASR, MNM and JC thank the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support.
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