organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-N-Acetyl­amino-5-[N-acetyl-N-(tetra-O-acetyl-β-D-gluco­pyranos­yl)amino]-1,3-di­methyl­uracil

CROSSMARK_Color_square_no_text.svg

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

(Received 1 February 2006; accepted 3 February 2006; online 8 February 2006)

The title compound, C24H32N4O13, crystallizes with two molecules in the asymmetric unit. 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)[link], has been prepared for use as an inter­mediate in the synthesis of nucleoside analogues with potential anti­tumour or anti­viral applications.

[Scheme 1]

Compound (I)[link] crystallizes with two independent mol­ecules (Fig. 1[link]) in the space group P21, and the two mol­ecules have very similar conformations. In the glucopyran­ose rings, the ring-puckering parameters (Cremer & Pople, 1975[Cremer, D. & Pople, J. A. (1975). J. Amer. Chem. Soc. 97, 1354-1358.]) in mol­ecules 1 and 2 (containing N11 and N31 respectively, Fig. 1[link]) 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[link]), 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[link]), forming an S(7) motif (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]), and these inter­actions may have an influence on the overall mol­ecular conformations.

There are no significant direction-specific inter­molecular inter­actions.

[Figure 1]
Figure 1
One of the two independent mol­ecules of compound (I)[link], viz. mol­ecule 1, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
One of the two independent mol­ecules of compound (I)[link], viz. mol­ecule 2, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Experimental

Crystals of compound (I)[link] were prepared according to a published procedure (Melgarejo Sampedro et al., 1982[Melgarejo Sampedro, M., Rodríguez Melgarejo, C., Rico Gomez, R. & Sánchez Rodrigo, A. (1982). An. Quim. Ser. C, 78, 93-97.]).

Crystal data
  • C24H32N4O13

  • Mr = 584.54

  • Monoclinic, P 21

  • a = 8.8490 (1) Å

  • b = 17.8429 (2) Å

  • c = 18.3058 (2) Å

  • β = 103.7830 (8)°

  • V = 2807.11 (6) Å3

  • Z = 4

  • Dx = 1.383 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 6642 reflections

  • θ = 2.9–27.5°

  • μ = 0.11 mm−1

  • T = 120 (2) K

  • Block, colourless

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker–Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan(SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.])Tmin = 0.954, Tmax = 0.980

  • 46614 measured reflections

  • 6642 independent reflections

  • 5791 reflections with I > 2σ(I)

  • Rint = 0.037

  • θmax = 27.5°

  • h = −11 → 10

  • k = −22 → 23

  • l = −23 → 23

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.087

  • S = 1.08

  • 6642 reflections

  • 755 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0458P)2 + 0.4658P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Selected geometric parameters (Å, °)

N11—C12 1.382 (3)
C12—N13 1.386 (3)
N13—C14 1.376 (3)
C14—C15 1.361 (3)
C15—C16 1.449 (3)
C16—N11 1.400 (3)
N31—C32 1.368 (4)
C32—N33 1.396 (3)
N33—C34 1.374 (3)
C34—C35 1.362 (3)
C35—C36 1.448 (3)
C36—N31 1.389 (3)
C15—C14—N14—C141 −116.1 (2)
C15—N15—C21—C22 −35.7 (3)
C22—C21—N15—C151 151.98 (19)
C21—C22—O22—C221 129.62 (18)
C22—C23—O23—C231 −150.68 (18)
C23—C24—O24—C241 104.9 (2)
C24—C25—C26—O26 61.3 (3)
C25—C26—O26—C261 −136.4 (2)
C35—C34—N34—C341 −120.4 (2)
C35—N35—C41—C42 −27.7 (3)
C42—C41—N35—C351 145.74 (19)
C41—C42—O42—C421 132.84 (19)
C42—C43—O43—C431 −146.41 (19)
C43—C44—O44—C441 100.1 (2)
C44—C45—C46—O46 49.3 (3)
C45—C46—O46—C461 −124.2 (2)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA 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

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 anomalous scattering, the Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) parameter was indeterminate (Flack & Bernard­inelli, 2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]); hence, the Friedel equivalents were merged prior to the final refinements. The absolute configuration 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[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10, Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: 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).

4-N-Acetylamino-5-[N-acetyl-N-(tetra-O-acetyl-β-D– glucopyranosyl)amino]-1,3-dimethyluracil top
Crystal data top
C24H32N4O13F(000) = 1232
Mr = 584.54Dx = 1.383 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6642 reflections
a = 8.8490 (1) Åθ = 2.9–27.5°
b = 17.8429 (2) ŵ = 0.11 mm1
c = 18.3058 (2) ÅT = 120 K
β = 103.7830 (8)°Block, colourless
V = 2807.11 (6) Å30.22 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker–Nonius KappaCCD
diffractometer
6642 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode5791 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
φ and ω scansh = 1110
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 2223
Tmin = 0.954, Tmax = 0.980l = 2323
46614 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-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 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.27 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.9337 (2)0.42742 (12)0.83728 (10)0.0222 (4)
C110.8141 (3)0.38198 (16)0.85942 (15)0.0339 (6)
C121.0086 (2)0.48112 (14)0.88748 (12)0.0225 (5)
O120.96987 (19)0.49537 (11)0.94561 (9)0.0310 (4)
N131.1308 (2)0.51828 (11)0.86795 (10)0.0221 (4)
C131.1979 (3)0.58236 (15)0.91553 (14)0.0294 (5)
C141.1807 (2)0.50003 (13)0.80455 (12)0.0201 (4)
N141.3161 (2)0.53533 (11)0.79646 (11)0.0230 (4)
C1411.4590 (3)0.52158 (14)0.84579 (13)0.0238 (5)
O1411.47059 (19)0.48102 (11)0.89996 (9)0.0308 (4)
C1421.5929 (3)0.56229 (16)0.82671 (15)0.0307 (5)
C151.0978 (2)0.45189 (12)0.75244 (12)0.0190 (4)
N151.1450 (2)0.43373 (10)0.68527 (10)0.0185 (4)
C1511.2325 (3)0.37007 (13)0.67975 (13)0.0238 (5)
O1511.2766 (2)0.35754 (10)0.62307 (10)0.0310 (4)
C1521.2678 (3)0.31951 (16)0.74688 (17)0.0383 (7)
C211.1210 (2)0.48574 (12)0.62313 (12)0.0190 (4)
C220.9712 (2)0.53131 (12)0.61122 (11)0.0183 (4)
O220.84262 (17)0.47985 (9)0.59061 (8)0.0210 (3)
C2210.7297 (3)0.48458 (14)0.62960 (13)0.0246 (5)
O2210.7331 (2)0.53006 (11)0.67844 (10)0.0335 (4)
C2220.6069 (3)0.42667 (17)0.60451 (15)0.0356 (6)
C230.9632 (3)0.58685 (13)0.54700 (12)0.0202 (4)
O230.82640 (17)0.63257 (9)0.54400 (8)0.0209 (3)
C2310.7520 (3)0.66120 (13)0.47597 (12)0.0227 (5)
O2310.7882 (2)0.64737 (11)0.41852 (9)0.0351 (4)
C2320.6224 (3)0.71199 (16)0.48277 (14)0.0309 (5)
C241.1071 (3)0.63619 (13)0.56516 (12)0.0211 (4)
O241.1150 (2)0.68135 (9)0.50130 (9)0.0276 (4)
C2411.0788 (3)0.75487 (14)0.50305 (16)0.0316 (6)
O2411.0356 (3)0.78322 (11)0.55370 (13)0.0471 (5)
C2421.0978 (4)0.79121 (19)0.4323 (2)0.0530 (9)
C251.2550 (3)0.58918 (14)0.58160 (14)0.0254 (5)
C261.3980 (3)0.63618 (16)0.60911 (17)0.0363 (6)
O261.3865 (2)0.67209 (11)0.67852 (12)0.0399 (5)
C2611.4265 (3)0.74464 (17)0.6863 (2)0.0535 (9)
O2611.4703 (3)0.77954 (14)0.6391 (2)0.0902 (11)
C2621.4111 (4)0.7743 (2)0.7600 (3)0.0689 (12)
O251.25068 (17)0.53662 (9)0.63982 (9)0.0223 (3)
C160.9674 (2)0.41112 (13)0.76804 (12)0.0200 (4)
O160.89333 (18)0.36325 (9)0.72684 (9)0.0256 (3)
N310.7874 (2)0.58238 (13)0.27061 (12)0.0281 (4)
C310.9234 (3)0.61973 (18)0.25399 (18)0.0394 (7)
C320.8188 (3)0.52956 (15)0.32636 (14)0.0301 (5)
O320.9519 (2)0.51303 (12)0.35935 (12)0.0414 (5)
N330.6916 (2)0.49383 (12)0.34391 (11)0.0258 (4)
C330.7291 (3)0.43388 (16)0.40016 (14)0.0348 (6)
C340.5417 (2)0.51248 (13)0.30817 (12)0.0215 (4)
N340.4231 (2)0.47380 (11)0.33021 (10)0.0232 (4)
C3410.3989 (3)0.47838 (14)0.40223 (13)0.0260 (5)
O3410.4779 (2)0.51943 (11)0.44949 (9)0.0341 (4)
C3420.2728 (3)0.42821 (16)0.41584 (14)0.0330 (6)
C350.5133 (2)0.56315 (12)0.25089 (12)0.0202 (4)
N350.3594 (2)0.57824 (11)0.20807 (10)0.0197 (4)
C3510.2876 (3)0.64703 (13)0.21261 (13)0.0234 (5)
O3510.1687 (2)0.66401 (10)0.16741 (10)0.0317 (4)
C3520.3607 (3)0.69583 (15)0.27864 (16)0.0345 (6)
C410.2791 (2)0.52555 (13)0.15225 (12)0.0197 (4)
C420.3861 (2)0.47726 (13)0.11738 (12)0.0198 (4)
O420.46192 (17)0.52602 (9)0.07462 (8)0.0230 (3)
C4210.6186 (3)0.51840 (16)0.08439 (14)0.0308 (6)
O4210.6951 (2)0.47453 (13)0.12746 (11)0.0405 (5)
C4220.6813 (3)0.5733 (2)0.03738 (16)0.0430 (7)
C430.2922 (2)0.41926 (13)0.06475 (12)0.0205 (4)
O430.40424 (18)0.37114 (10)0.04277 (9)0.0241 (3)
C4310.3674 (3)0.34180 (14)0.02775 (13)0.0267 (5)
O4310.2442 (2)0.35106 (10)0.07145 (9)0.0313 (4)
C4320.5003 (3)0.29657 (17)0.04135 (16)0.0381 (6)
C440.1912 (2)0.37420 (13)0.10573 (12)0.0208 (4)
O440.08784 (18)0.32624 (9)0.05350 (9)0.0238 (3)
C4410.1278 (3)0.25301 (14)0.05120 (14)0.0268 (5)
O4410.2397 (2)0.22611 (11)0.09376 (12)0.0431 (5)
C4420.0179 (3)0.21355 (16)0.01072 (15)0.0343 (6)
C450.0903 (2)0.42695 (13)0.13932 (12)0.0210 (4)
C460.0091 (3)0.38646 (14)0.18349 (14)0.0269 (5)
O460.0868 (2)0.33473 (10)0.23564 (9)0.0303 (4)
C4610.0440 (3)0.26187 (16)0.23186 (16)0.0362 (6)
O4610.0687 (3)0.23867 (12)0.18726 (14)0.0560 (6)
C4620.1527 (4)0.2170 (2)0.2892 (2)0.0630 (10)
O450.19311 (17)0.47638 (9)0.19027 (8)0.0208 (3)
C360.6397 (3)0.60310 (13)0.23045 (12)0.0231 (5)
O360.6200 (2)0.65264 (10)0.18299 (9)0.0288 (4)
H11A0.81770.39060.91270.051*
H11B0.83320.32880.85150.051*
H11C0.71140.39610.82890.051*
H13A1.22220.62270.88380.044*
H13B1.29340.56650.95140.044*
H13C1.12290.60050.94310.044*
H141.31700.55180.75130.028*
H14A1.69090.54330.85820.046*
H14B1.58400.61600.83590.046*
H14C1.59130.55410.77360.046*
H15A1.33690.34540.78910.057*
H15B1.31880.27390.73490.057*
H15C1.17080.30610.76060.057*
H211.12200.45770.57590.023*
H220.96690.55850.65840.022*
H22A0.50700.44590.61060.053*
H22B0.63440.38130.63500.053*
H22C0.59870.41470.55150.053*
H230.95500.55990.49830.024*
H23A0.52330.68510.46770.046*
H23B0.62060.75560.45010.046*
H23C0.63810.72870.53510.046*
H241.10520.66900.60920.025*
H24A1.08660.84560.43620.080*
H24B1.01810.77230.38960.080*
H24C1.20130.77960.42480.080*
H251.26310.56170.53510.030*
H26A1.49220.60430.61800.044*
H26B1.40570.67450.57100.044*
H26C1.39900.82890.75690.103*
H26D1.50450.76160.79890.103*
H26E1.31970.75190.77290.103*
H31A0.88850.65700.21430.059*
H31B0.98910.58240.23720.059*
H31C0.98320.64460.29950.059*
H33A0.64420.39730.39130.052*
H33B0.74260.45530.45060.052*
H33C0.82560.40900.39620.052*
H340.34360.46020.29380.028*
H34A0.27980.42500.47000.050*
H34B0.28490.37810.39610.050*
H34C0.17120.44870.39030.050*
H35A0.29640.74060.27870.052*
H35B0.46500.71090.27490.052*
H35C0.36810.66780.32540.052*
H410.20470.55330.11150.024*
H420.46550.45180.15790.024*
H42A0.74290.54670.00770.065*
H42B0.74740.60990.07010.065*
H42C0.59480.59940.00350.065*
H430.22560.44440.01950.025*
H43A0.57830.33010.05370.057*
H43B0.46230.26200.08330.057*
H43C0.54750.26790.00400.057*
H440.25860.34340.14640.025*
H44A0.03430.15930.00500.051*
H44B0.03590.22970.05910.051*
H44C0.08920.22560.00890.051*
H450.02210.45700.09830.025*
H46A0.05740.42320.21150.032*
H46B0.09320.35870.14870.032*
H46C0.14980.16460.27270.095*
H46D0.12190.21990.33710.095*
H46E0.25850.23670.29570.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0198 (9)0.0288 (10)0.0191 (9)0.0010 (8)0.0065 (7)0.0038 (8)
C110.0324 (13)0.0385 (15)0.0363 (14)0.0042 (12)0.0191 (11)0.0055 (12)
C120.0204 (10)0.0279 (12)0.0197 (10)0.0061 (9)0.0056 (8)0.0028 (9)
O120.0294 (9)0.0424 (11)0.0227 (8)0.0060 (8)0.0094 (7)0.0000 (7)
N130.0214 (9)0.0252 (10)0.0196 (8)0.0030 (8)0.0049 (7)0.0017 (8)
C130.0330 (13)0.0272 (13)0.0285 (12)0.0001 (11)0.0087 (10)0.0056 (10)
C140.0204 (10)0.0189 (11)0.0213 (10)0.0029 (8)0.0053 (8)0.0028 (8)
N140.0225 (9)0.0246 (10)0.0225 (9)0.0028 (8)0.0065 (7)0.0024 (8)
C1410.0238 (10)0.0222 (11)0.0262 (11)0.0005 (9)0.0072 (9)0.0056 (10)
O1410.0261 (8)0.0342 (10)0.0306 (9)0.0010 (8)0.0037 (7)0.0067 (8)
C1420.0260 (12)0.0341 (14)0.0338 (13)0.0020 (11)0.0105 (10)0.0003 (11)
C150.0186 (10)0.0201 (11)0.0188 (10)0.0033 (8)0.0054 (8)0.0033 (8)
N150.0222 (9)0.0158 (9)0.0189 (8)0.0023 (7)0.0075 (7)0.0020 (7)
C1510.0245 (11)0.0189 (11)0.0311 (12)0.0010 (9)0.0124 (9)0.0022 (9)
O1510.0367 (9)0.0242 (9)0.0385 (10)0.0059 (8)0.0214 (8)0.0011 (8)
C1520.0442 (15)0.0298 (14)0.0467 (16)0.0162 (12)0.0221 (13)0.0153 (12)
C210.0223 (10)0.0171 (10)0.0190 (10)0.0006 (9)0.0079 (8)0.0013 (8)
C220.0202 (10)0.0169 (11)0.0178 (9)0.0009 (8)0.0048 (8)0.0004 (8)
O220.0218 (7)0.0201 (8)0.0210 (7)0.0037 (6)0.0051 (6)0.0012 (6)
C2210.0204 (10)0.0288 (13)0.0250 (11)0.0041 (9)0.0059 (9)0.0088 (10)
O2210.0314 (9)0.0349 (10)0.0395 (10)0.0028 (8)0.0190 (8)0.0008 (9)
C2220.0237 (12)0.0434 (16)0.0364 (14)0.0070 (11)0.0011 (10)0.0132 (12)
C230.0242 (11)0.0181 (10)0.0192 (10)0.0018 (9)0.0071 (8)0.0008 (9)
O230.0228 (7)0.0210 (8)0.0187 (7)0.0027 (6)0.0044 (6)0.0022 (6)
C2310.0270 (11)0.0170 (11)0.0214 (11)0.0030 (9)0.0002 (9)0.0027 (9)
O2310.0504 (11)0.0337 (10)0.0195 (8)0.0097 (9)0.0051 (8)0.0009 (7)
C2320.0283 (12)0.0347 (14)0.0296 (12)0.0053 (11)0.0071 (10)0.0105 (11)
C240.0272 (11)0.0168 (11)0.0212 (10)0.0014 (9)0.0095 (9)0.0046 (9)
O240.0358 (9)0.0216 (8)0.0277 (8)0.0004 (7)0.0123 (7)0.0083 (7)
C2410.0246 (12)0.0198 (12)0.0477 (16)0.0014 (10)0.0036 (11)0.0078 (11)
O2410.0585 (13)0.0217 (10)0.0628 (13)0.0037 (9)0.0181 (11)0.0002 (10)
C2420.0512 (18)0.0389 (17)0.073 (2)0.0054 (15)0.0228 (16)0.0313 (17)
C250.0278 (12)0.0217 (12)0.0303 (12)0.0021 (9)0.0143 (10)0.0090 (10)
C260.0249 (12)0.0330 (14)0.0540 (17)0.0003 (11)0.0153 (12)0.0174 (13)
O260.0329 (10)0.0285 (10)0.0522 (12)0.0107 (8)0.0019 (9)0.0062 (9)
C2610.0239 (13)0.0250 (15)0.109 (3)0.0006 (12)0.0101 (16)0.0023 (18)
O2610.0767 (18)0.0241 (12)0.191 (3)0.0010 (12)0.073 (2)0.0165 (17)
C2620.0379 (17)0.045 (2)0.112 (3)0.0048 (15)0.0069 (19)0.020 (2)
O250.0213 (7)0.0208 (8)0.0259 (8)0.0002 (6)0.0080 (6)0.0073 (7)
C160.0186 (10)0.0198 (11)0.0210 (10)0.0028 (9)0.0034 (8)0.0054 (9)
O160.0275 (8)0.0236 (9)0.0254 (8)0.0045 (7)0.0058 (7)0.0024 (7)
N310.0203 (9)0.0318 (11)0.0322 (10)0.0026 (9)0.0063 (8)0.0091 (9)
C310.0235 (12)0.0430 (16)0.0549 (17)0.0101 (12)0.0154 (12)0.0140 (14)
C320.0247 (12)0.0291 (13)0.0343 (13)0.0048 (10)0.0028 (10)0.0119 (11)
O320.0220 (8)0.0410 (11)0.0568 (12)0.0068 (8)0.0005 (8)0.0081 (10)
N330.0237 (10)0.0252 (10)0.0246 (9)0.0021 (8)0.0020 (8)0.0033 (8)
C330.0359 (14)0.0311 (14)0.0311 (13)0.0067 (11)0.0042 (11)0.0029 (11)
C340.0221 (10)0.0201 (11)0.0200 (10)0.0014 (9)0.0003 (8)0.0051 (9)
N340.0239 (9)0.0248 (10)0.0182 (9)0.0022 (8)0.0002 (7)0.0012 (8)
C3410.0274 (11)0.0242 (12)0.0244 (11)0.0062 (10)0.0023 (9)0.0039 (10)
O3410.0427 (10)0.0342 (10)0.0238 (8)0.0014 (9)0.0049 (7)0.0037 (8)
C3420.0338 (13)0.0368 (15)0.0287 (12)0.0002 (11)0.0080 (10)0.0050 (11)
C350.0188 (10)0.0199 (11)0.0210 (10)0.0015 (9)0.0026 (8)0.0052 (9)
N350.0195 (8)0.0187 (9)0.0194 (9)0.0000 (7)0.0014 (7)0.0017 (7)
C3510.0246 (11)0.0203 (11)0.0278 (11)0.0009 (9)0.0111 (9)0.0027 (9)
O3510.0300 (9)0.0290 (9)0.0345 (9)0.0103 (8)0.0045 (7)0.0023 (8)
C3520.0339 (13)0.0267 (13)0.0436 (15)0.0003 (11)0.0104 (12)0.0106 (11)
C410.0199 (10)0.0195 (11)0.0191 (10)0.0016 (9)0.0034 (8)0.0013 (9)
C420.0217 (10)0.0196 (11)0.0181 (10)0.0007 (9)0.0047 (8)0.0017 (9)
O420.0218 (7)0.0267 (9)0.0213 (7)0.0036 (7)0.0066 (6)0.0003 (7)
C4210.0238 (11)0.0411 (15)0.0292 (12)0.0053 (11)0.0094 (10)0.0156 (12)
O4210.0231 (8)0.0505 (12)0.0469 (11)0.0029 (9)0.0061 (8)0.0090 (10)
C4220.0385 (15)0.060 (2)0.0354 (14)0.0221 (14)0.0191 (12)0.0139 (14)
C430.0212 (10)0.0201 (11)0.0191 (10)0.0021 (9)0.0028 (8)0.0001 (9)
O430.0256 (8)0.0252 (9)0.0217 (7)0.0024 (7)0.0060 (6)0.0028 (7)
C4310.0357 (13)0.0224 (12)0.0242 (11)0.0041 (10)0.0114 (10)0.0015 (9)
O4310.0372 (10)0.0328 (10)0.0234 (8)0.0057 (8)0.0064 (7)0.0040 (7)
C4320.0443 (15)0.0375 (15)0.0370 (14)0.0038 (13)0.0185 (12)0.0096 (12)
C440.0218 (10)0.0193 (11)0.0191 (10)0.0022 (9)0.0007 (8)0.0010 (9)
O440.0254 (8)0.0209 (8)0.0230 (8)0.0033 (7)0.0016 (6)0.0020 (6)
C4410.0327 (13)0.0197 (12)0.0287 (12)0.0023 (10)0.0089 (10)0.0006 (10)
O4410.0492 (12)0.0245 (10)0.0480 (11)0.0074 (9)0.0038 (9)0.0015 (9)
C4420.0391 (14)0.0262 (13)0.0376 (14)0.0090 (11)0.0091 (11)0.0087 (11)
C450.0188 (10)0.0213 (11)0.0211 (10)0.0021 (9)0.0014 (8)0.0010 (9)
C460.0237 (11)0.0282 (13)0.0290 (12)0.0030 (10)0.0067 (9)0.0000 (10)
O460.0324 (9)0.0314 (10)0.0257 (8)0.0070 (8)0.0041 (7)0.0058 (7)
C4610.0409 (15)0.0307 (14)0.0413 (15)0.0063 (12)0.0183 (12)0.0046 (12)
O4610.0584 (14)0.0305 (11)0.0720 (15)0.0144 (11)0.0011 (12)0.0006 (11)
C4620.057 (2)0.056 (2)0.073 (2)0.0048 (18)0.0116 (18)0.040 (2)
O450.0211 (7)0.0202 (8)0.0209 (7)0.0042 (6)0.0049 (6)0.0013 (6)
C360.0235 (11)0.0236 (12)0.0223 (11)0.0033 (9)0.0055 (9)0.0094 (9)
O360.0332 (9)0.0261 (9)0.0283 (8)0.0067 (7)0.0097 (7)0.0033 (7)
Geometric parameters (Å, º) top
N11—C121.382 (3)N31—C321.368 (4)
C12—N131.386 (3)C32—N331.396 (3)
N13—C141.376 (3)N33—C341.374 (3)
C14—C151.361 (3)C34—C351.362 (3)
C15—C161.449 (3)C35—C361.448 (3)
C16—N111.400 (3)C36—N311.389 (3)
N11—C111.465 (3)N31—C311.469 (3)
C11—H11A0.98C31—H31A0.98
C11—H11B0.98C31—H31B0.98
C11—H11C0.98C31—H31C0.98
C12—O121.220 (3)C32—O321.225 (3)
N13—C131.474 (3)N33—C331.467 (3)
C13—H13A0.98C33—H33A0.98
C13—H13B0.98C33—H33B0.98
C13—H13C0.98C33—H33C0.98
C14—N141.392 (3)C34—N341.394 (3)
N14—C1411.389 (3)N34—C3411.387 (3)
N14—H140.88N34—H340.8799
C141—O1411.212 (3)C341—O3411.219 (3)
C141—C1421.500 (3)C341—C3421.497 (4)
C142—H14A0.98C342—H34A0.98
C142—H14B0.98C342—H34B0.98
C142—H14C0.98C342—H34C0.98
C15—N151.427 (3)C35—N351.426 (3)
N15—C1511.392 (3)N35—C3511.394 (3)
N15—C211.444 (3)N35—C411.445 (3)
C151—O1511.213 (3)C351—O3511.212 (3)
C151—C1521.496 (3)C351—C3521.505 (3)
C152—H15A0.98C352—H35A0.98
C152—H15B0.98C352—H35B0.98
C152—H15C0.98C352—H35C0.98
C21—O251.438 (3)C41—O451.444 (3)
C21—C221.526 (3)C41—C421.528 (3)
C21—H211.00C41—H411.00
C22—O221.441 (3)C42—O421.439 (3)
C22—C231.526 (3)C42—C431.520 (3)
C22—H221.00C42—H421.00
O22—C2211.362 (3)O42—C4211.362 (3)
C221—O2211.202 (3)C421—O4211.199 (3)
C221—C2221.491 (4)C421—C4221.496 (4)
C222—H22A0.98C422—H42A0.98
C222—H22B0.98C422—H42B0.98
C222—H22C0.98C422—H42C0.98
C23—O231.450 (3)C43—O431.440 (3)
C23—C241.518 (3)C43—C441.525 (3)
C23—H231.00C43—H431.00
O23—C2311.362 (3)O43—C4311.359 (3)
C231—O2311.196 (3)C431—O4311.201 (3)
C231—C2321.490 (3)C431—C4321.495 (4)
C232—H23A0.98C432—H43A0.98
C232—H23B0.98C432—H43B0.98
C232—H23C0.98C432—H43C0.98
C24—O241.435 (3)C44—O441.438 (3)
C24—C251.523 (3)C44—C451.524 (3)
C24—H241.00C44—H441.00
O24—C2411.353 (3)O44—C4411.357 (3)
C241—O2411.196 (3)C441—O4411.205 (3)
C241—C2421.493 (4)C441—C4421.484 (4)
C242—H24A0.98C442—H44A0.98
C242—H24B0.98C442—H44B0.98
C242—H24C0.98C442—H44C0.98
C25—O251.427 (3)C45—O451.439 (3)
C25—C261.501 (4)C45—C461.512 (3)
C25—H251.00C45—H451.00
C26—O261.448 (4)C46—O461.448 (3)
C26—H26A0.99C46—H46A0.99
C26—H26B0.99C46—H46B0.99
O26—C2611.340 (4)O46—C4611.351 (3)
C261—O2611.203 (5)C461—O4611.202 (4)
C261—C2621.485 (6)C461—C4621.478 (4)
C262—H26C0.98C462—H46C0.98
C262—H26D0.98C462—H46D0.98
C262—H26E0.98C462—H46E0.98
C16—O161.222 (3)C36—O361.222 (3)
C12—N11—C16125.05 (19)C32—N31—C36125.2 (2)
C12—N11—C11117.59 (18)C32—N31—C31115.9 (2)
C16—N11—C11117.3 (2)C36—N31—C31118.9 (2)
N11—C11—H11A109.5N31—C31—H31A109.5
N11—C11—H11B109.5N31—C31—H31B109.5
H11A—C11—H11B109.5H31A—C31—H31B109.5
N11—C11—H11C109.5N31—C31—H31C109.5
H11A—C11—H11C109.5H31A—C31—H31C109.5
H11B—C11—H11C109.5H31B—C31—H31C109.5
O12—C12—N11122.3 (2)O32—C32—N31122.3 (2)
O12—C12—N13121.6 (2)O32—C32—N33120.7 (2)
N11—C12—N13116.10 (18)N31—C32—N33117.1 (2)
C14—N13—C12122.11 (19)C34—N33—C32121.4 (2)
C14—N13—C13121.10 (19)C34—N33—C33122.8 (2)
C12—N13—C13116.64 (18)C32—N33—C33115.8 (2)
N13—C13—H13A109.5N33—C33—H33A109.5
N13—C13—H13B109.5N33—C33—H33B109.5
H13A—C13—H13B109.5H33A—C33—H33B109.5
N13—C13—H13C109.5N33—C33—H33C109.5
H13A—C13—H13C109.5H33A—C33—H33C109.5
H13B—C13—H13C109.5H33B—C33—H33C109.5
C15—C14—N13120.84 (19)C35—C34—N33120.5 (2)
C15—C14—N14123.00 (19)C35—C34—N34122.57 (19)
N13—C14—N14116.12 (19)N33—C34—N34116.8 (2)
C141—N14—C14121.60 (19)C341—N34—C34122.88 (19)
C141—N14—H14117.4C341—N34—H34117.4
C14—N14—H14116.9C34—N34—H34116.0
O141—C141—N14121.6 (2)O341—C341—N34121.2 (2)
O141—C141—C142124.2 (2)O341—C341—C342124.4 (2)
N14—C141—C142114.2 (2)N34—C341—C342114.4 (2)
C141—C142—H14A109.5C341—C342—H34A109.5
C141—C142—H14B109.5C341—C342—H34B109.5
H14A—C142—H14B109.5H34A—C342—H34B109.5
C141—C142—H14C109.5C341—C342—H34C109.5
H14A—C142—H14C109.5H34A—C342—H34C109.5
H14B—C142—H14C109.5H34B—C342—H34C109.5
C14—C15—N15121.86 (19)C34—C35—N35121.69 (19)
C14—C15—C16120.02 (19)C34—C35—C36120.9 (2)
N15—C15—C16117.79 (19)N35—C35—C36117.39 (19)
C151—N15—C15122.01 (18)C351—N35—C35121.52 (18)
C151—N15—C21116.55 (17)C351—N35—C41117.44 (18)
C15—N15—C21120.98 (17)C35—N35—C41120.70 (18)
O151—C151—N15120.7 (2)O351—C351—N35120.9 (2)
O151—C151—C152123.0 (2)O351—C351—C352122.7 (2)
N15—C151—C152116.3 (2)N35—C351—C352116.3 (2)
C151—C152—H15A109.5C351—C352—H35A109.5
C151—C152—H15B109.5C351—C352—H35B109.5
H15A—C152—H15B109.5H35A—C352—H35B109.5
C151—C152—H15C109.5C351—C352—H35C109.5
H15A—C152—H15C109.5H35A—C352—H35C109.5
H15B—C152—H15C109.5H35B—C352—H35C109.5
O25—C21—N15106.16 (17)O45—C41—N35106.34 (16)
O25—C21—C22108.43 (17)O45—C41—C42107.99 (18)
N15—C21—C22114.49 (17)N35—C41—C42114.37 (17)
O25—C21—H21109.2O45—C41—H41109.3
N15—C21—H21109.2N35—C41—H41109.3
C22—C21—H21109.2C42—C41—H41109.3
O22—C22—C21107.64 (17)O42—C42—C43108.81 (16)
O22—C22—C23108.88 (16)O42—C42—C41107.58 (18)
C21—C22—C23109.58 (17)C43—C42—C41110.40 (17)
O22—C22—H22110.2O42—C42—H42110.0
C21—C22—H22110.2C43—C42—H42110.0
C23—C22—H22110.2C41—C42—H42110.0
C221—O22—C22117.10 (17)C421—O42—C42117.39 (19)
O221—C221—O22122.7 (2)O421—C421—O42123.3 (2)
O221—C221—C222125.7 (2)O421—C421—C422125.3 (2)
O22—C221—C222111.6 (2)O42—C421—C422111.4 (2)
C221—C222—H22A109.5C421—C422—H42A109.5
C221—C222—H22B109.5C421—C422—H42B109.5
H22A—C222—H22B109.5H42A—C422—H42B109.5
C221—C222—H22C109.5C421—C422—H42C109.5
H22A—C222—H22C109.5H42A—C422—H42C109.5
H22B—C222—H22C109.5H42B—C422—H42C109.5
O23—C23—C24109.34 (18)O43—C43—C42105.90 (17)
O23—C23—C22106.22 (16)O43—C43—C44110.25 (18)
C24—C23—C22108.99 (17)C42—C43—C44110.08 (17)
O23—C23—H23110.7O43—C43—H43110.2
C24—C23—H23110.7C42—C43—H43110.2
C22—C23—H23110.7C44—C43—H43110.2
C231—O23—C23117.58 (16)C431—O43—C43118.04 (17)
O231—C231—O23123.7 (2)O431—C431—O43123.7 (2)
O231—C231—C232124.9 (2)O431—C431—C432126.1 (2)
O23—C231—C232111.46 (19)O43—C431—C432110.2 (2)
C231—C232—H23A109.5C431—C432—H43A109.5
C231—C232—H23B109.5C431—C432—H43B109.5
H23A—C232—H23B109.5H43A—C432—H43B109.5
C231—C232—H23C109.5C431—C432—H43C109.5
H23A—C232—H23C109.5H43A—C432—H43C109.5
H23B—C232—H23C109.5H43B—C432—H43C109.5
O24—C24—C23110.38 (18)O44—C44—C45107.13 (17)
O24—C24—C25105.31 (17)O44—C44—C43109.95 (17)
C23—C24—C25111.12 (19)C45—C44—C43109.94 (19)
O24—C24—H24110.0O44—C44—H44109.9
C23—C24—H24110.0C45—C44—H44109.9
C25—C24—H24110.0C43—C44—H44109.9
C241—O24—C24117.9 (2)C441—O44—C44117.69 (18)
O241—C241—O24123.4 (2)O441—C441—O44122.9 (2)
O241—C241—C242127.7 (3)O441—C441—C442126.4 (2)
O24—C241—C242108.9 (2)O44—C441—C442110.6 (2)
C241—C242—H24A109.5C441—C442—H44A109.5
C241—C242—H24B109.5C441—C442—H44B109.5
H24A—C242—H24B109.5H44A—C442—H44B109.5
C241—C242—H24C109.5C441—C442—H44C109.5
H24A—C242—H24C109.5H44A—C442—H44C109.5
H24B—C242—H24C109.5H44B—C442—H44C109.5
O25—C25—C26106.7 (2)O45—C45—C46107.73 (18)
O25—C25—C24109.56 (17)O45—C45—C44107.40 (17)
C26—C25—C24112.0 (2)C46—C45—C44113.1 (2)
O25—C25—H25109.5O45—C45—H45109.5
C26—C25—H25109.5C46—C45—H45109.5
C24—C25—H25109.5C44—C45—H45109.5
O26—C26—C25108.2 (2)O46—C46—C45109.44 (18)
O26—C26—H26A110.1O46—C46—H46A109.8
C25—C26—H26A110.1C45—C46—H46A109.8
O26—C26—H26B110.1O46—C46—H46B109.8
C25—C26—H26B110.1C45—C46—H46B109.8
H26A—C26—H26B108.4H46A—C46—H46B108.2
C261—O26—C26116.7 (3)C461—O46—C46117.8 (2)
O261—C261—O26123.0 (4)O461—C461—O46122.9 (3)
O261—C261—C262125.7 (3)O461—C461—C462126.1 (3)
O26—C261—C262111.2 (3)O46—C461—C462111.0 (3)
C261—C262—H26C109.5C461—C462—H46C109.5
C261—C262—H26D109.5C461—C462—H46D109.5
H26C—C262—H26D109.5H46C—C462—H46D109.5
C261—C262—H26E109.5C461—C462—H46E109.5
H26C—C262—H26E109.5H46C—C462—H46E109.5
H26D—C262—H26E109.5H46D—C462—H46E109.5
C25—O25—C21114.74 (17)C45—O45—C41112.60 (15)
O16—C16—N11120.4 (2)O36—C36—N31121.7 (2)
O16—C16—C15124.4 (2)O36—C36—C35123.5 (2)
N11—C16—C15115.17 (19)N31—C36—C35114.8 (2)
C16—N11—C12—O12176.6 (2)C36—N31—C32—O32179.2 (2)
C11—N11—C12—O125.9 (3)C31—N31—C32—O321.6 (3)
C16—N11—C12—N133.2 (3)C36—N31—C32—N330.1 (3)
C11—N11—C12—N13174.2 (2)C31—N31—C32—N33179.3 (2)
O12—C12—N13—C14176.5 (2)O32—C32—N33—C34179.1 (2)
N11—C12—N13—C143.6 (3)N31—C32—N33—C341.8 (3)
O12—C12—N13—C137.8 (3)O32—C32—N33—C333.2 (3)
N11—C12—N13—C13172.08 (19)N31—C32—N33—C33175.9 (2)
C12—N13—C14—C159.6 (3)C32—N33—C34—C354.4 (3)
C13—N13—C14—C15165.9 (2)C33—N33—C34—C35173.1 (2)
C12—N13—C14—N14172.39 (19)C32—N33—C34—N34179.6 (2)
C13—N13—C14—N1412.1 (3)C33—N33—C34—N342.9 (3)
C15—C14—N14—C141116.1 (2)C35—C34—N34—C341120.4 (2)
N13—C14—N14—C14165.9 (3)N33—C34—N34—C34163.6 (3)
C14—N14—C141—O1413.5 (3)C34—N34—C341—O3413.0 (3)
C14—N14—C141—C142177.8 (2)C34—N34—C341—C342175.8 (2)
N13—C14—C15—N15178.24 (19)N33—C34—C35—N35173.9 (2)
N14—C14—C15—N150.3 (3)N34—C34—C35—N351.9 (3)
N13—C14—C15—C168.6 (3)N33—C34—C35—C365.2 (3)
N14—C14—C15—C16173.5 (2)N34—C34—C35—C36179.0 (2)
C14—C15—N15—C15195.6 (3)C34—C35—N35—C351111.6 (2)
C16—C15—N15—C15177.7 (3)C36—C35—N35—C35169.3 (3)
C14—C15—N15—C2176.4 (3)C34—C35—N35—C4175.3 (3)
C16—C15—N15—C21110.3 (2)C36—C35—N35—C41103.8 (2)
C15—N15—C151—O151176.9 (2)C35—N35—C351—O351167.5 (2)
C21—N15—C151—O1514.7 (3)C41—N35—C351—O3515.8 (3)
C15—N15—C151—C1523.0 (3)C35—N35—C351—C35215.9 (3)
C21—N15—C151—C152175.3 (2)C41—N35—C351—C352170.74 (19)
C151—N15—C21—O2588.4 (2)C351—N35—C41—O4595.2 (2)
C15—N15—C21—O2583.9 (2)C35—N35—C41—O4591.4 (2)
C15—N15—C21—C2235.7 (3)C35—N35—C41—C4227.7 (3)
C22—C21—N15—C151151.98 (19)C42—C41—N35—C351145.74 (19)
O25—C21—C22—O22176.96 (15)O45—C41—C42—O42175.45 (15)
N15—C21—C22—O2264.7 (2)N35—C41—C42—O4266.4 (2)
O25—C21—C22—C2358.7 (2)O45—C41—C42—C4356.9 (2)
N15—C21—C22—C23177.02 (18)N35—C41—C42—C43175.01 (17)
C21—C22—O22—C221129.62 (18)C43—C42—O42—C421107.5 (2)
C23—C22—O22—C221111.7 (2)C41—C42—O42—C421132.84 (19)
C22—O22—C221—O2211.3 (3)C42—O42—C421—O4211.5 (3)
C22—O22—C221—C222178.03 (19)C42—O42—C421—C422179.14 (19)
O22—C22—C23—O2367.9 (2)O42—C42—C43—O4369.3 (2)
C21—C22—C23—O23174.63 (16)C41—C42—C43—O43172.81 (16)
O22—C22—C23—C24174.41 (17)O42—C42—C43—C44171.48 (17)
C21—C22—C23—C2456.9 (2)C41—C42—C43—C4453.6 (2)
C24—C23—O23—C23191.9 (2)C42—C43—O43—C431146.41 (19)
C22—C23—O23—C231150.68 (18)C44—C43—O43—C43194.5 (2)
C23—O23—C231—O2314.2 (3)C43—O43—C431—O4313.4 (3)
C23—O23—C231—C232175.15 (19)C43—O43—C431—C432177.3 (2)
O23—C23—C24—O2472.9 (2)O43—C43—C44—O4471.0 (2)
C22—C23—C24—O24171.37 (17)C42—C43—C44—O44172.54 (17)
O23—C23—C24—C25170.63 (17)O43—C43—C44—C45171.30 (16)
C22—C23—C24—C2554.9 (2)C42—C43—C44—C4554.8 (2)
C23—C24—O24—C241104.9 (2)C45—C44—O44—C441140.4 (2)
C25—C24—O24—C241135.0 (2)C43—C44—O44—C441100.1 (2)
C24—O24—C241—O2412.7 (4)C44—O44—C441—O4414.7 (3)
C24—O24—C241—C242178.8 (2)C44—O44—C441—C442174.13 (19)
O24—C24—C25—O25174.16 (18)O44—C44—C45—O45178.58 (16)
C23—C24—C25—O2554.6 (2)C43—C44—C45—O4559.1 (2)
O24—C24—C25—C2667.7 (2)O44—C44—C45—C4662.7 (2)
C23—C24—C25—C26172.82 (19)C43—C44—C45—C46177.84 (18)
O25—C25—C26—O2658.6 (2)O45—C45—C46—O4669.2 (2)
C24—C25—C26—O2661.3 (3)C44—C45—C46—O4649.3 (3)
C25—C26—O26—C261136.4 (2)C45—C46—O46—C461124.2 (2)
C26—O26—C261—O2610.2 (4)C46—O46—C461—O4610.3 (4)
C26—O26—C261—C262179.4 (2)C46—O46—C461—C462179.4 (2)
C26—C25—O25—C21179.44 (19)C46—C45—O45—C41172.08 (18)
C24—C25—O25—C2159.1 (2)C44—C45—O45—C4165.8 (2)
N15—C21—O25—C25175.11 (17)N35—C41—O45—C45172.14 (16)
C22—C21—O25—C2561.4 (2)C42—C41—O45—C4564.7 (2)
C12—N11—C16—O16179.0 (2)C32—N31—C36—O36177.5 (2)
C11—N11—C16—O163.5 (3)C31—N31—C36—O361.7 (3)
C12—N11—C16—C153.9 (3)C32—N31—C36—C350.8 (3)
C11—N11—C16—C15173.5 (2)C31—N31—C36—C35180.0 (2)
C14—C15—C16—O16174.9 (2)C34—C35—C36—O36174.9 (2)
N15—C15—C16—O161.4 (3)N35—C35—C36—O366.0 (3)
C14—C15—C16—N112.1 (3)C34—C35—C36—N313.4 (3)
N15—C15—C16—N11175.51 (18)N35—C35—C36—N31175.75 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N14—H14···O250.882.002.787 (3)148
N34—H34···O450.882.062.867 (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.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Amer. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFlack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143–1148.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10, Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
First citationMelgarejo Sampedro, M., Rodríguez Melgarejo, C., Rico Gomez, R. & Sánchez Rodrigo, A. (1982). An. Quim. Ser. C, 78, 93–97.  CAS Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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