supplementary materials


pv2644 scheme

Acta Cryst. (2013). E69, o1517-o1518    [ doi:10.1107/S1600536813024586 ]

Ethyl 1'-methyl-2-oxo-4'-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl]-2H-spiro[acenaphthylene-1,2'-pyrrolidine]-3'-carboxylate

G. Jagadeesan, K. Sethusankar, R. Prasanna and R. Raghunathan

Abstract top

In the title molecule, C30H35NO8, the acenaphthylenone moiety, two atoms of a methyl pyrrolidine ring (N and C atoms) and four atoms of an ethyl acetate moiety (two C and two O atoms) are disordered over two sets of sites in ratio 0.532 (7):0.468 (7). The three C atoms of a dimethoxyethane ring and dioxolane ring attached with two methyl groups are disordered over two sets of sites in 0.66 (2):0.34 (2) and 0.62 (2):0.38 (2) ratios, respectively. The major and minor components of the acenaphthylene ring are essentially planar (r.m.s. deviations = 0.0254 and 0.0436 Å, respectively). The major and minor components of the pyrrolidine ring adopt C-envelope conformations with C atoms displaced by 0.492 (11) and 0.595 (7) Å from the remaining ring atoms. One of the dioxolane rings is disordered with its major component in an envelope conformation [C displaced by 0.511 (11) Å] and the minor fraction is more or less planar with an r.m.s. deviation of 0.070 Å. The other dioxolane ring is in an envelope conformation, with a C atom displaced by 0.438 (3) Å from the remainder of the ring atoms. The crystal packing features C-H...O interactions, which generate C(9) chains.

Comment top

The design and novel synthesis of glycospiroheterocycles are interesting because of the synthetic challenges they present and their biological profile against viruses, bacteria, and cancer cells (Ferguson et al., 2005). Pyrrolidines and pyrroles are common structural motifs in drugs and drug candidates owing to their ability to act as selective glycosidase inhibitors, which are used in the treatment of diabetes, cancer, malaria and viral infections, including AIDS (Kilonda et al., 1995).

In the title molecule, the acenaphthylenone moiety (O1, C1–C12), two atoms of a methyl pyrrolidine ring (N1 & C11) and four atoms of an ethyl acetate moiety (O2, O3, C18 & C19) were disordered over two sites in ratio 0.531 (7):0.469 (7). The three C atoms of a dimethoxyethane ring (C25, C26 & C27) and two methyl C atoms (C29 & C30) attached to a dioxolane ring were disordered over two sites in ratios 0.659 (2):0.341 (2) and 0.615 (7): 0.385 (7), respectively. The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in a closely related compound (Jagadeesan et al., 2012).

The major and minor components of the acenaphthylene ring (O1/C1–C12 and O1'/C1'–C12') are essentially planar (rmsd 0.0254 and 0.0436 Å, respectively). The major and minor components of pyrrolidine (C11/C14–C16/N1 & C11'/C14–C16/N1') adopt C11- and C14-envelope conformations with C atoms displaced by 0.492 (11) and 0.595 (7) °, respectively, from the remaining ring atoms. One of the dioxolane rings is disordered with major component (O5/O6/C21/C22/C25) in a C25-envelope conformation (C25 displaced by 0.511 (11) Å from the remining ring atoms) and the minor fraction (O5/O6/C21/C22/C25') is more or less planar with rmsd 0.070 Å. The other dioxolane ring (O7/O8/C23/C24/C28) is in a C28-envepole conmformation with C28 displaced by 0.438 (3) Å from the rest of the ring atoms.

The dihedral angle between the mean planes of the major acenaphthylenone moiety (C1–C12/O1) and major pyrrolidine ring (C11/C14/C15/C16/N1) is 82.91 (2)°, which shows they are almost orthogonal to each other. The mean plane of the pyran ring (C20–C24/O4) forms dihedral angles of 71.40 (2)° and 73.35 (1)° with the mean planes of the major dioxolane ring (C21/C22/C25/O5/O6) and undisordered dioxolane ring (C23/C24/C28/O7/O8), respectively.

The crystal packing is stabilized by C23—H23···O1 intermolecular interaction (Table 1 & Fig. 2) that generates a C(9) chain running along the c-axis.

Related literature top

For biological properties of spiroheterocycles, see: Kilonda et al. (1995); Ferguson et al. (2005). For a related crystal structure, see: Jagadeesan et al. (2012).

Experimental top

A mixture of (E)-ethyl 3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7 -tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5 - b:4',5'-d] pyran-5-yl)acrylate (0.915 mmol, 300 mg), acenaphthenequinone (0.915 mmol, 166 mg) and sarcosine (1.0 mmol, 97 mg) was refluxed in toluene for about 7 h under Dean stark reaction condition to give the title compound in good yield. After the completion of reaction as indicated by TLC, solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using hexane: EtOAc (7:3) as eluent.

Refinement top

In the acenaphthylenone moiety (C1–C12/O1), N1 and C13 atoms of the methyl pyrrolidine ring and C18/C19/O2/O3 atoms of the ethyl acetate moiety were disordered over two positions with the site occupancy factors 0.531 (7):0.469 (7). The dimethoxyethane ring C25/C26/C27 atoms and dioxolane ring attached with two methyl groups C29/C30 atoms were disordered over two positions with the site occupancy factors 0.659 (2):0.341 (2) and 0.615 (7): 0.385 (7). The bond distances of the major and minor components were restrained to a value of d(C–C) =1.39 (1) Å for aromatic ring, d(C–C) = 1.50 (1) Å for aliphatic ring and d(C–O) = 1.30 (1) Å, respectively. The bond distances of the disordered components were restrained using standard similarity restraint SADI [SHELXL97, Sheldrick, 2008] with s.u. of 0.01 Å. Hydrogen atoms were placed in calculated positions with C–H = 0.93 to 0.98 Å refined in the riding model with fixed isotropic displacement parameters: Uiso(H) = 1.5 Ueq(C) for methyl group and Uiso(H) = 1.2 Ueq(C) for other groups. In the absence of significant anomalous dispersion effects, an absolute structure was not deternined and 1505 Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme, displacement ellipsoids are drawn at 30% probability level. H–atoms are present as small spheres of arbitary radius. The minor fractions of the disordered carbon atoms have been represented by broken bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down c axis. Dashed lines indicates C23—H23···O1 interaction generates a C(9) chain, H–atoms not involved in hydrogen bonds have been excluded for clarity.
Ethyl 1'-methyl-2-oxo-4'-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl]-2H-spiro[acenaphthylene-1,2'-pyrrolidine]-3'-carboxylate top
Crystal data top
C30H35NO8F(000) = 1144
Mr = 537.59Dx = 1.243 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 5184 reflections
a = 17.3582 (15) Åθ = 2.2–25.2°
b = 18.5489 (13) ŵ = 0.09 mm1
c = 8.9213 (8) ÅT = 293 K
V = 2872.4 (4) Å3Block, colourless
Z = 40.30 × 0.25 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5184 independent reflections
Radiation source: fine-focus sealed tube3771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
/w scansθmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 2020
Tmin = 0.974, Tmax = 0.978k = 1322
14399 measured reflectionsl = 106
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.2077P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.004
5184 reflectionsΔρmax = 0.13 e Å3
572 parametersΔρmin = 0.11 e Å3
332 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0099 (8)
Crystal data top
C30H35NO8V = 2872.4 (4) Å3
Mr = 537.59Z = 4
Orthorhombic, P21212Mo Kα radiation
a = 17.3582 (15) ŵ = 0.09 mm1
b = 18.5489 (13) ÅT = 293 K
c = 8.9213 (8) Å0.30 × 0.25 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5184 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
3771 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.978Rint = 0.030
14399 measured reflectionsθmax = 25.2°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.099Δρmax = 0.13 e Å3
S = 1.03Δρmin = 0.11 e Å3
5184 reflectionsAbsolute structure: ?
572 parametersAbsolute structure parameter: ?
332 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C160.15148 (12)0.19659 (12)0.2054 (3)0.0535 (6)
H160.17710.21190.29790.064*
C150.06795 (12)0.18045 (12)0.2491 (3)0.0491 (6)
H150.03500.18720.16100.059*
C140.07115 (14)0.10032 (12)0.2866 (3)0.0587 (7)
H14A0.05720.09260.39060.070*0.532 (7)
H14B0.03530.07380.22390.070*0.532 (7)
H14C0.05740.09260.39080.070*0.468 (7)
H14D0.03510.07390.22420.070*0.468 (7)
C170.16164 (17)0.25778 (15)0.0965 (4)0.0683 (8)
C200.04071 (11)0.23067 (12)0.3727 (3)0.0463 (6)
H200.05130.28020.34050.056*
C210.08472 (12)0.27183 (12)0.6098 (3)0.0529 (6)
H210.10400.25320.70550.064*
C220.00533 (13)0.30468 (12)0.6337 (3)0.0614 (7)
H220.00380.31220.74100.074*
C230.06041 (12)0.26220 (12)0.5663 (3)0.0572 (6)
H230.10620.29290.55810.069*
C240.04390 (11)0.22622 (12)0.4148 (3)0.0526 (6)
H240.07530.24880.33650.063*
C280.10639 (14)0.14752 (14)0.5737 (4)0.0681 (7)
O40.08668 (8)0.21659 (8)0.50278 (16)0.0480 (4)
O50.13093 (8)0.33014 (8)0.5643 (2)0.0675 (5)
O60.00947 (8)0.37183 (9)0.5595 (3)0.0797 (6)
O70.06725 (9)0.15371 (8)0.4351 (2)0.0636 (5)
O80.07565 (10)0.20380 (9)0.6640 (2)0.0694 (5)
O10.3046 (4)0.1229 (5)0.3207 (9)0.0774 (19)0.532 (7)
C110.1889 (7)0.1245 (6)0.1623 (12)0.049 (2)0.532 (7)
C10.1841 (6)0.1164 (10)0.0021 (11)0.058 (3)0.532 (7)
C20.1246 (4)0.1115 (3)0.1031 (7)0.0631 (17)0.532 (7)
H20.07390.11290.06990.076*0.532 (7)
C30.1407 (5)0.1041 (3)0.2559 (8)0.078 (2)0.532 (7)
H30.09970.10130.32290.093*0.532 (7)
C40.2155 (6)0.1009 (6)0.3116 (12)0.078 (3)0.532 (7)
H40.22410.09750.41430.093*0.532 (7)
C50.2777 (5)0.1028 (4)0.2117 (9)0.0700 (19)0.532 (7)
C60.3561 (6)0.1006 (4)0.2442 (11)0.087 (3)0.532 (7)
H60.37080.09720.34410.104*0.532 (7)
C70.4139 (7)0.1034 (8)0.1350 (12)0.086 (3)0.532 (7)
H70.46550.10190.16310.103*0.532 (7)
C80.3941 (5)0.1083 (5)0.0151 (11)0.077 (2)0.532 (7)
H80.43240.10920.08800.092*0.532 (7)
C90.3175 (6)0.1119 (10)0.0562 (14)0.052 (3)0.532 (7)
C120.2596 (7)0.1098 (10)0.057 (2)0.056 (3)0.532 (7)
C100.2752 (5)0.1185 (8)0.1970 (10)0.047 (2)0.532 (7)
N10.1465 (3)0.0764 (2)0.2608 (7)0.0540 (14)0.532 (7)
C130.1440 (10)0.0046 (9)0.1778 (15)0.082 (4)0.532 (7)
H13A0.19570.02080.15910.124*0.532 (7)
H13B0.11670.00100.08450.124*0.532 (7)
H13C0.11840.03840.24210.124*0.532 (7)
O20.1136 (5)0.2854 (7)0.0177 (18)0.079 (2)0.532 (7)
O30.2367 (3)0.2687 (6)0.0732 (13)0.056 (2)0.532 (7)
C180.2624 (5)0.3178 (6)0.0435 (13)0.074 (2)0.532 (7)
H18A0.24710.36680.02010.088*0.532 (7)
H18B0.24020.30450.13940.088*0.532 (7)
C190.3474 (4)0.3117 (7)0.0484 (11)0.084 (3)0.532 (7)
H19A0.36760.34550.11980.125*0.532 (7)
H19B0.36150.26370.07750.125*0.532 (7)
H19C0.36820.32210.04890.125*0.532 (7)
O1'0.2724 (5)0.1030 (5)0.3368 (9)0.085 (3)0.468 (7)
C11'0.1821 (9)0.1253 (7)0.1322 (13)0.049 (3)0.468 (7)
C1'0.2002 (6)0.1177 (11)0.0318 (10)0.044 (2)0.468 (7)
C2'0.1593 (4)0.1205 (4)0.1638 (9)0.0592 (19)0.468 (7)
H2'0.10630.12740.15880.071*0.468 (7)
C3'0.1933 (6)0.1136 (8)0.3043 (12)0.067 (3)0.468 (7)
H3'0.16270.11170.38980.080*0.468 (7)
C4'0.2739 (5)0.1096 (4)0.3166 (8)0.069 (2)0.468 (7)
H4'0.29650.10880.41110.082*0.468 (7)
C5'0.3204 (5)0.1068 (4)0.1898 (9)0.0534 (18)0.468 (7)
C6'0.4005 (6)0.1004 (8)0.1857 (11)0.058 (2)0.468 (7)
H6'0.42840.09960.27460.069*0.468 (7)
C7'0.4388 (4)0.0952 (4)0.0480 (9)0.0644 (19)0.468 (7)
H7'0.49220.09110.04740.077*0.468 (7)
C8'0.3991 (5)0.0959 (4)0.0894 (8)0.0536 (18)0.468 (7)
H8'0.42530.09050.17970.064*0.468 (7)
C9'0.3192 (7)0.1050 (12)0.0864 (16)0.051 (3)0.468 (7)
C12'0.2810 (6)0.1100 (11)0.054 (2)0.042 (2)0.468 (7)
C10'0.2599 (8)0.1107 (11)0.1996 (11)0.064 (3)0.468 (7)
N1'0.1207 (3)0.0695 (2)0.1654 (8)0.0585 (17)0.468 (7)
C13'0.1557 (12)0.0010 (11)0.2335 (15)0.058 (3)0.468 (7)
H13D0.18840.02190.16090.087*0.468 (7)
H13E0.11520.03150.26170.087*0.468 (7)
H13F0.18540.01350.32040.087*0.468 (7)
O2'0.1099 (8)0.2973 (9)0.059 (2)0.129 (8)0.468 (7)
O3'0.2356 (4)0.2741 (9)0.085 (2)0.105 (5)0.468 (7)
C18'0.2517 (10)0.3333 (8)0.016 (2)0.129 (5)0.468 (7)
H18C0.26340.37680.03930.155*0.468 (7)
H18D0.20790.34250.08110.155*0.468 (7)
C19'0.3189 (10)0.3102 (9)0.1052 (19)0.170 (7)0.468 (7)
H19D0.32910.34510.18210.256*0.468 (7)
H19E0.30840.26420.15040.256*0.468 (7)
H19F0.36310.30610.04080.256*0.468 (7)
C250.0875 (2)0.3946 (3)0.5826 (13)0.061 (2)0.66 (2)
C260.1071 (7)0.4412 (6)0.4537 (17)0.101 (3)0.66 (2)
H26A0.15910.45830.46400.152*0.66 (2)
H26B0.07250.48160.45070.152*0.66 (2)
H26C0.10250.41410.36250.152*0.66 (2)
C270.1041 (6)0.4301 (5)0.7319 (14)0.085 (3)0.66 (2)
H27A0.15730.44400.73610.128*0.66 (2)
H27B0.09310.39690.81150.128*0.66 (2)
H27C0.07230.47220.74280.128*0.66 (2)
C25'0.0876 (4)0.3935 (6)0.528 (2)0.070 (4)0.34 (2)
C26'0.1038 (12)0.4293 (11)0.382 (3)0.087 (5)0.34 (2)
H26D0.15760.44080.37540.131*0.34 (2)
H26E0.07410.47280.37430.131*0.34 (2)
H26F0.09010.39750.30110.131*0.34 (2)
C27'0.0992 (11)0.4457 (10)0.656 (3)0.090 (4)0.34 (2)
H27D0.15000.46600.65030.136*0.34 (2)
H27E0.09330.42060.74950.136*0.34 (2)
H27F0.06170.48360.64970.136*0.34 (2)
C290.1910 (4)0.1618 (14)0.539 (3)0.087 (4)0.62 (7)
H29A0.22080.15810.62890.130*0.62 (7)
H29B0.20900.12690.46720.130*0.62 (7)
H29C0.19650.20930.49730.130*0.62 (7)
C300.0907 (13)0.0786 (8)0.658 (3)0.099 (5)0.62 (7)
H30A0.11890.07880.75060.148*0.62 (7)
H30B0.03650.07490.67890.148*0.62 (7)
H30C0.10660.03820.59840.148*0.62 (7)
C29'0.1936 (5)0.151 (3)0.576 (6)0.114 (9)0.38 (7)
H29D0.21170.14560.67690.171*0.38 (7)
H29E0.21430.11350.51450.171*0.38 (7)
H29F0.21010.19720.53770.171*0.38 (7)
C30'0.076 (3)0.0750 (12)0.623 (5)0.102 (7)0.38 (7)
H30D0.09610.06390.72090.153*0.38 (7)
H30E0.02100.07630.62660.153*0.38 (7)
H30F0.09260.03870.55330.153*0.38 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C160.0525 (13)0.0476 (14)0.0605 (16)0.0024 (10)0.0128 (12)0.0054 (11)
C150.0474 (12)0.0501 (14)0.0497 (14)0.0003 (10)0.0018 (12)0.0016 (11)
C140.0614 (15)0.0507 (15)0.0639 (16)0.0090 (11)0.0201 (13)0.0079 (12)
C170.0784 (19)0.0495 (17)0.077 (2)0.0011 (14)0.0238 (18)0.0040 (14)
C200.0404 (11)0.0421 (12)0.0565 (15)0.0036 (9)0.0029 (11)0.0053 (11)
C210.0498 (12)0.0470 (14)0.0621 (16)0.0004 (10)0.0026 (12)0.0089 (11)
C220.0536 (13)0.0470 (15)0.0836 (19)0.0000 (10)0.0104 (14)0.0166 (13)
C230.0389 (11)0.0485 (14)0.0841 (18)0.0018 (9)0.0092 (13)0.0101 (14)
C240.0403 (11)0.0522 (14)0.0652 (16)0.0022 (10)0.0047 (12)0.0021 (12)
C280.0573 (14)0.0652 (17)0.082 (2)0.0200 (12)0.0146 (15)0.0097 (15)
O40.0451 (8)0.0437 (9)0.0551 (9)0.0092 (6)0.0045 (7)0.0042 (7)
O50.0417 (8)0.0460 (9)0.1148 (15)0.0002 (7)0.0007 (10)0.0064 (10)
O60.0441 (9)0.0443 (10)0.1506 (18)0.0040 (7)0.0031 (12)0.0044 (11)
O70.0514 (9)0.0599 (11)0.0795 (12)0.0121 (7)0.0149 (10)0.0162 (9)
O80.0685 (11)0.0665 (12)0.0732 (12)0.0185 (9)0.0115 (10)0.0105 (10)
O10.067 (4)0.104 (4)0.061 (4)0.002 (3)0.015 (3)0.007 (3)
C110.048 (5)0.050 (4)0.050 (4)0.002 (3)0.011 (3)0.011 (3)
C10.070 (5)0.042 (3)0.061 (5)0.000 (4)0.009 (4)0.000 (4)
C20.080 (4)0.054 (3)0.055 (4)0.002 (3)0.004 (3)0.002 (3)
C30.116 (5)0.067 (3)0.051 (4)0.002 (4)0.020 (4)0.002 (3)
C40.129 (7)0.064 (5)0.039 (4)0.002 (6)0.001 (5)0.010 (3)
C50.111 (5)0.044 (3)0.055 (4)0.004 (4)0.027 (4)0.005 (3)
C60.119 (7)0.062 (4)0.080 (5)0.002 (4)0.047 (5)0.014 (4)
C70.085 (6)0.084 (5)0.089 (7)0.001 (5)0.046 (6)0.007 (6)
C80.065 (4)0.079 (4)0.087 (6)0.005 (3)0.023 (5)0.012 (5)
C90.047 (4)0.051 (5)0.057 (6)0.004 (3)0.018 (4)0.017 (4)
C120.092 (6)0.039 (3)0.038 (4)0.005 (6)0.014 (6)0.006 (3)
C100.040 (3)0.055 (4)0.045 (5)0.005 (3)0.013 (3)0.013 (3)
N10.051 (2)0.048 (2)0.064 (3)0.0023 (17)0.014 (2)0.010 (2)
C130.097 (9)0.040 (5)0.110 (11)0.007 (5)0.055 (8)0.005 (7)
O20.070 (4)0.074 (4)0.093 (5)0.013 (3)0.018 (4)0.032 (4)
O30.060 (4)0.049 (4)0.057 (4)0.006 (3)0.017 (3)0.007 (3)
C180.080 (4)0.049 (4)0.092 (5)0.004 (3)0.045 (4)0.017 (4)
C190.082 (4)0.094 (5)0.075 (6)0.021 (4)0.031 (4)0.025 (4)
O1'0.092 (6)0.126 (7)0.036 (3)0.042 (5)0.003 (4)0.009 (3)
C11'0.050 (5)0.046 (4)0.050 (6)0.000 (3)0.005 (4)0.006 (4)
C1'0.054 (5)0.047 (4)0.032 (4)0.008 (4)0.007 (4)0.006 (3)
C2'0.064 (4)0.065 (4)0.048 (4)0.014 (3)0.015 (4)0.010 (4)
C3'0.089 (6)0.070 (5)0.041 (5)0.034 (4)0.020 (4)0.002 (4)
C4'0.104 (5)0.062 (4)0.039 (4)0.017 (4)0.001 (4)0.004 (3)
C5'0.065 (4)0.048 (3)0.048 (4)0.010 (4)0.013 (4)0.002 (3)
C6'0.058 (5)0.063 (4)0.052 (5)0.003 (4)0.017 (4)0.007 (4)
C7'0.060 (4)0.070 (4)0.063 (5)0.000 (3)0.014 (4)0.007 (3)
C8'0.066 (4)0.046 (3)0.049 (4)0.003 (3)0.003 (4)0.001 (3)
C9'0.065 (5)0.041 (4)0.047 (5)0.000 (4)0.002 (4)0.002 (4)
C12'0.059 (4)0.033 (4)0.034 (4)0.004 (4)0.010 (4)0.001 (3)
C10'0.085 (7)0.072 (6)0.036 (5)0.016 (6)0.015 (4)0.008 (4)
N1'0.061 (3)0.043 (3)0.072 (4)0.010 (2)0.020 (3)0.013 (3)
C13'0.072 (5)0.042 (4)0.060 (7)0.011 (3)0.014 (5)0.009 (5)
O2'0.132 (8)0.100 (8)0.155 (15)0.055 (6)0.069 (7)0.067 (9)
O3'0.116 (8)0.082 (8)0.117 (9)0.040 (6)0.047 (6)0.008 (6)
C18'0.164 (9)0.085 (8)0.139 (9)0.023 (7)0.088 (7)0.021 (6)
C19'0.273 (17)0.091 (8)0.147 (13)0.052 (10)0.113 (12)0.041 (8)
C250.045 (3)0.041 (3)0.098 (6)0.003 (2)0.003 (2)0.004 (3)
C260.083 (5)0.080 (5)0.141 (9)0.003 (4)0.003 (5)0.024 (5)
C270.081 (4)0.063 (4)0.112 (7)0.004 (3)0.019 (5)0.027 (4)
C25'0.044 (5)0.049 (6)0.115 (10)0.004 (4)0.008 (5)0.009 (5)
C26'0.050 (5)0.063 (7)0.148 (13)0.025 (5)0.018 (9)0.034 (9)
C27'0.061 (6)0.085 (8)0.125 (12)0.003 (5)0.016 (8)0.022 (8)
C290.041 (4)0.120 (7)0.099 (9)0.026 (4)0.030 (3)0.033 (7)
C300.114 (6)0.066 (5)0.117 (13)0.023 (4)0.036 (6)0.000 (5)
C29'0.073 (9)0.147 (15)0.122 (17)0.042 (8)0.020 (8)0.019 (13)
C30'0.159 (17)0.074 (8)0.072 (12)0.011 (8)0.019 (13)0.011 (7)
Geometric parameters (Å, º) top
C16—C171.504 (4)O3—C181.454 (6)
C16—C151.531 (3)C18—C191.480 (8)
C16—C111.535 (8)C18—H18A0.9700
C16—C11'1.568 (9)C18—H18B0.9700
C16—H160.9800C19—H19A0.9600
C15—C201.519 (3)C19—H19B0.9600
C15—C141.524 (3)C19—H19C0.9600
C15—H150.9800O1'—C10'1.251 (9)
C14—N11.400 (4)C11'—C10'1.503 (9)
C14—N1'1.496 (6)C11'—C1'1.503 (9)
C14—H14A0.9700C11'—N1'1.515 (18)
C14—H14B0.9700C1'—C2'1.376 (8)
C14—H14C0.9700C1'—C12'1.422 (9)
C14—H14D0.9700C2'—C3'1.391 (9)
C17—O21.204 (7)C2'—H2'0.9300
C17—O2'1.208 (8)C3'—C4'1.406 (9)
C17—O3'1.323 (7)C3'—H3'0.9300
C17—O31.335 (6)C4'—C5'1.391 (8)
C20—O41.433 (2)C4'—H4'0.9300
C20—C241.518 (3)C5'—C6'1.395 (9)
C20—H200.9800C5'—C12'1.40 (2)
C21—O41.401 (3)C6'—C7'1.401 (8)
C21—O51.406 (3)C6'—H6'0.9300
C21—C221.522 (3)C7'—C8'1.407 (8)
C21—H210.9800C7'—H7'0.9300
C22—O61.412 (3)C8'—C9'1.398 (9)
C22—C231.512 (3)C8'—H8'0.9300
C22—H220.9800C9'—C12'1.42 (2)
C23—O81.415 (3)C9'—C10'1.445 (9)
C23—C241.534 (3)N1'—C13'1.53 (2)
C23—H230.9800C13'—H13D0.9600
C24—O71.416 (3)C13'—H13E0.9600
C24—H240.9800C13'—H13F0.9600
C28—O71.415 (3)O3'—C18'1.447 (8)
C28—O81.423 (3)C18'—C19'1.474 (10)
C28—C301.509 (7)C18'—H18C0.9700
C28—C30'1.508 (9)C18'—H18D0.9700
C28—C29'1.516 (9)C19'—H19D0.9600
C28—C291.525 (7)C19'—H19E0.9600
O5—C251.423 (5)C19'—H19F0.9600
O5—C25'1.433 (8)C25—C261.479 (8)
O6—C251.435 (5)C25—C271.513 (7)
O6—C25'1.442 (8)C26—H26A0.9600
O1—C101.219 (8)C26—H26B0.9600
C11—N11.453 (15)C26—H26C0.9600
C11—C11.477 (8)C27—H27A0.9600
C11—C101.533 (9)C27—H27B0.9600
C1—C21.373 (8)C27—H27C0.9600
C1—C121.405 (9)C25'—C26'1.489 (11)
C2—C31.398 (7)C25'—C27'1.513 (10)
C2—H20.9300C26'—H26D0.9600
C3—C41.392 (8)C26'—H26E0.9600
C3—H30.9300C26'—H26F0.9600
C4—C51.401 (9)C27'—H27D0.9600
C4—H40.9300C27'—H27E0.9600
C5—C61.391 (8)C27'—H27F0.9600
C5—C121.42 (2)C29—H29A0.9600
C6—C71.400 (9)C29—H29B0.9600
C6—H60.9300C29—H29C0.9600
C7—C81.385 (9)C30—H30A0.9600
C7—H70.9300C30—H30B0.9600
C8—C91.381 (8)C30—H30C0.9600
C8—H80.9300C29'—H29D0.9600
C9—C121.43 (2)C29'—H29E0.9600
C9—C101.461 (8)C29'—H29F0.9600
N1—C131.675 (16)C30'—H30D0.9600
C13—H13A0.9600C30'—H30E0.9600
C13—H13B0.9600C30'—H30F0.9600
C13—H13C0.9600
C17—C16—C15115.0 (2)H13A—C13—H13C109.5
C17—C16—C11116.5 (5)H13B—C13—H13C109.5
C15—C16—C11107.1 (6)C17—O3—C18120.4 (7)
C17—C16—C11'109.2 (6)O3—C18—C19106.2 (7)
C15—C16—C11'105.2 (7)O3—C18—H18A110.5
C17—C16—H16105.8C19—C18—H18A110.5
C15—C16—H16105.8O3—C18—H18B110.5
C11—C16—H16105.8C19—C18—H18B110.5
C11'—C16—H16116.2H18A—C18—H18B108.7
C20—C15—C14116.78 (19)C18—C19—H19A109.5
C20—C15—C16111.10 (19)C18—C19—H19B109.5
C14—C15—C16102.25 (17)H19A—C19—H19B109.5
C20—C15—H15108.8C18—C19—H19C109.5
C14—C15—H15108.8H19A—C19—H19C109.5
C16—C15—H15108.8H19B—C19—H19C109.5
N1—C14—C15107.9 (2)C10'—C11'—C1'100.6 (9)
N1'—C14—C15103.6 (3)C10'—C11'—N1'115.5 (11)
N1—C14—H14A110.1C1'—C11'—N1'105.8 (10)
N1'—C14—H14A141.2C10'—C11'—C16106.9 (11)
C15—C14—H14A110.1C1'—C11'—C16123.8 (12)
N1—C14—H14B110.1N1'—C11'—C16104.9 (8)
N1'—C14—H14B76.0C2'—C1'—C12'113.3 (11)
C15—C14—H14B110.1C2'—C1'—C11'136.2 (10)
H14A—C14—H14B108.4C12'—C1'—C11'110.4 (12)
N1—C14—H14C109.8C1'—C2'—C3'123.3 (8)
N1'—C14—H14C141.0C1'—C2'—H2'118.3
C15—C14—H14C110.1C3'—C2'—H2'118.3
H14B—C14—H14C108.7C2'—C3'—C4'119.8 (9)
N1—C14—H14D110.3C2'—C3'—H3'120.1
N1'—C14—H14D76.3C4'—C3'—H3'120.1
C15—C14—H14D110.1C5'—C4'—C3'121.1 (9)
H14A—C14—H14D108.2C5'—C4'—H4'119.5
H14C—C14—H14D108.5C3'—C4'—H4'119.5
O2—C17—O3'121.8 (9)C6'—C5'—C4'127.0 (8)
O2'—C17—O3'124.1 (11)C6'—C5'—C12'118.0 (9)
O2—C17—O3121.3 (8)C4'—C5'—C12'115.0 (9)
O2'—C17—O3126.2 (10)C5'—C6'—C7'120.2 (9)
O2—C17—C16128.0 (6)C5'—C6'—H6'119.9
O2'—C17—C16123.4 (10)C7'—C6'—H6'119.9
O3'—C17—C16109.8 (7)C6'—C7'—C8'122.1 (8)
O3—C17—C16109.2 (5)C6'—C7'—H7'119.0
O4—C20—C24109.18 (18)C8'—C7'—H7'119.0
O4—C20—C15107.62 (16)C9'—C8'—C7'118.1 (8)
C24—C20—C15116.58 (19)C9'—C8'—H8'121.0
O4—C20—H20107.7C7'—C8'—H8'121.0
C24—C20—H20107.7C8'—C9'—C12'119.3 (11)
C15—C20—H20107.7C8'—C9'—C10'134.6 (12)
O4—C21—O5110.61 (19)C12'—C9'—C10'106.1 (10)
O4—C21—C22114.25 (19)C5'—C12'—C9'122.4 (9)
O5—C21—C22104.42 (19)C5'—C12'—C1'127.3 (15)
O4—C21—H21109.1C9'—C12'—C1'110.3 (14)
O5—C21—H21109.1O1'—C10'—C9'123.5 (12)
C22—C21—H21109.1O1'—C10'—C11'124.5 (10)
O6—C22—C23108.2 (2)C9'—C10'—C11'111.9 (10)
O6—C22—C21103.96 (19)C14—N1'—C11'106.5 (5)
C23—C22—C21114.76 (19)C14—N1'—C13'105.0 (8)
O6—C22—H22109.9C11'—N1'—C13'111.4 (9)
C23—C22—H22109.9N1'—C13'—H13D109.5
C21—C22—H22109.9N1'—C13'—H13E109.5
O8—C23—C22107.2 (2)H13D—C13'—H13E109.5
O8—C23—C24104.16 (18)N1'—C13'—H13F109.5
C22—C23—C24115.87 (18)H13D—C13'—H13F109.5
O8—C23—H23109.8H13E—C13'—H13F109.5
C22—C23—H23109.8C17—O3'—C18'114.3 (12)
C24—C23—H23109.8O3'—C18'—C19'105.5 (12)
O7—C24—C20111.12 (17)O3'—C18'—H18C110.6
O7—C24—C23104.28 (19)C19'—C18'—H18C110.6
C20—C24—C23112.02 (18)O3'—C18'—H18D110.6
O7—C24—H24109.8C19'—C18'—H18D110.6
C20—C24—H24109.8H18C—C18'—H18D108.8
C23—C24—H24109.8C18'—C19'—H19D109.5
O7—C28—O8104.78 (17)C18'—C19'—H19E109.5
O7—C28—C30114.7 (12)H19D—C19'—H19E109.5
O8—C28—C30105.8 (11)C18'—C19'—H19F109.5
O7—C28—C30'99.3 (19)H19D—C19'—H19F109.5
O8—C28—C30'111.0 (17)H19E—C19'—H19F109.5
O7—C28—C29'119 (2)O5—C25—O6103.7 (3)
O8—C28—C29'109.5 (17)O5—C25—C26106.3 (7)
C30—C28—C29'102 (2)O6—C25—C26106.1 (6)
C30'—C28—C29'113 (2)O5—C25—C27111.5 (5)
O7—C28—C29105.6 (10)O6—C25—C27115.7 (7)
O8—C28—C29110.5 (9)C26—C25—C27112.7 (5)
C30—C28—C29115.1 (13)C25—C26—H26A109.5
C30'—C28—C29123.2 (19)C25—C26—H26B109.5
C21—O4—C20113.90 (16)H26A—C26—H26B109.5
C21—O5—C25108.1 (3)C25—C26—H26C109.5
C21—O5—C25'113.4 (4)H26A—C26—H26C109.5
C22—O6—C25103.9 (3)H26B—C26—H26C109.5
C22—O6—C25'112.7 (4)C25—C27—H27A109.5
C28—O7—C24109.05 (18)C25—C27—H27B109.5
C23—O8—C28106.4 (2)H27A—C27—H27B109.5
N1—C11—C1120.7 (11)C25—C27—H27C109.5
N1—C11—C10109.2 (8)H27A—C27—H27C109.5
C1—C11—C10104.3 (8)H27B—C27—H27C109.5
N1—C11—C1699.8 (7)O5—C25'—O6102.7 (6)
C1—C11—C16108.2 (10)O5—C25'—C26'117.8 (12)
C10—C11—C16115.2 (10)O6—C25'—C26'118.3 (12)
C2—C1—C12117.8 (11)O5—C25'—C27'106.4 (11)
C2—C1—C11134.5 (10)O6—C25'—C27'98.9 (11)
C12—C1—C11107.7 (11)C26'—C25'—C27'110.6 (11)
C1—C2—C3119.8 (8)C25'—C26'—H26D109.5
C1—C2—H2120.1C25'—C26'—H26E109.5
C3—C2—H2120.1H26D—C26'—H26E109.5
C4—C3—C2122.6 (8)C25'—C26'—H26F109.5
C4—C3—H3118.7H26D—C26'—H26F109.5
C2—C3—H3118.7H26E—C26'—H26F109.5
C3—C4—C5119.4 (9)C25'—C27'—H27D109.5
C3—C4—H4120.3C25'—C27'—H27E109.5
C5—C4—H4120.3H27D—C27'—H27E109.5
C6—C5—C4128.4 (8)C25'—C27'—H27F109.5
C6—C5—C12114.9 (9)H27D—C27'—H27F109.5
C4—C5—C12116.7 (8)H27E—C27'—H27F109.5
C5—C6—C7123.7 (9)C28—C29—H29A109.5
C5—C6—H6118.1C28—C29—H29B109.5
C7—C6—H6118.1H29A—C29—H29B109.5
C8—C7—C6119.8 (10)C28—C29—H29C109.5
C8—C7—H7120.1H29A—C29—H29C109.5
C6—C7—H7120.1H29B—C29—H29C109.5
C7—C8—C9119.9 (9)C28—C30—H30A109.5
C7—C8—H8120.0C28—C30—H30B109.5
C9—C8—H8120.0H30A—C30—H30B109.5
C8—C9—C12119.3 (11)C28—C30—H30C109.5
C8—C9—C10135.8 (11)H30A—C30—H30C109.5
C12—C9—C10104.9 (9)H30B—C30—H30C109.5
C1—C12—C5123.6 (13)C28—C29'—H29D109.5
C1—C12—C9114.1 (14)C28—C29'—H29E109.5
C5—C12—C9122.3 (10)H29D—C29'—H29E109.5
O1—C10—C9124.9 (10)C28—C29'—H29F109.5
O1—C10—C11126.0 (9)H29D—C29'—H29F109.5
C9—C10—C11108.9 (8)H29E—C29'—H29F109.5
C14—N1—C11112.2 (5)C28—C30'—H30D109.5
C14—N1—C13109.5 (8)C28—C30'—H30E109.5
C11—N1—C13107.2 (8)H30D—C30'—H30E109.5
N1—C13—H13A109.5C28—C30'—H30F109.5
N1—C13—H13B109.5H30D—C30'—H30F109.5
H13A—C13—H13B109.5H30E—C30'—H30F109.5
N1—C13—H13C109.5
C17—C16—C15—C2082.5 (3)C12—C9—C10—C113.1 (17)
C11—C16—C15—C20146.3 (4)N1—C11—C10—O150.4 (17)
C11'—C16—C15—C20157.3 (5)C1—C11—C10—O1179.3 (14)
C17—C16—C15—C14152.2 (2)C16—C11—C10—O160.8 (18)
C11—C16—C15—C1421.0 (5)N1—C11—C10—C9133.7 (11)
C11'—C16—C15—C1432.0 (5)C1—C11—C10—C93.4 (16)
C20—C15—C14—N1123.3 (3)C16—C11—C10—C9115.1 (12)
C16—C15—C14—N11.8 (4)N1'—C14—N1—C1169.9 (6)
C20—C15—C14—N1'163.6 (3)C15—C14—N1—C1119.8 (7)
C16—C15—C14—N1'42.1 (4)N1'—C14—N1—C1349.0 (8)
C15—C16—C17—O216.5 (11)C15—C14—N1—C13138.7 (6)
C11—C16—C17—O2110.0 (12)C1—C11—N1—C1486.4 (10)
C11'—C16—C17—O2101.5 (12)C10—C11—N1—C14152.9 (7)
C15—C16—C17—O2'8.5 (12)C16—C11—N1—C1431.7 (8)
C11—C16—C17—O2'135.0 (13)C1—C11—N1—C1333.8 (12)
C11'—C16—C17—O2'126.4 (13)C10—C11—N1—C1386.9 (10)
C15—C16—C17—O3'170.4 (10)C16—C11—N1—C13151.9 (8)
C11—C16—C17—O3'63.0 (11)O2—C17—O3—C183.6 (16)
C11'—C16—C17—O3'71.6 (11)O2'—C17—O3—C1820.7 (18)
C15—C16—C17—O3177.0 (6)O3'—C17—O3—C1893 (9)
C11—C16—C17—O356.4 (8)C16—C17—O3—C18171.2 (8)
C11'—C16—C17—O365.0 (9)C17—O3—C18—C19174.7 (12)
C14—C15—C20—O453.0 (2)C17—C16—C11'—C10'102.4 (10)
C16—C15—C20—O463.7 (2)C15—C16—C11'—C10'133.6 (10)
C14—C15—C20—C2470.0 (3)C11—C16—C11'—C10'32 (6)
C16—C15—C20—C24173.3 (2)C17—C16—C11'—C1'13.4 (15)
O4—C21—C22—O6104.8 (2)C15—C16—C11'—C1'110.6 (13)
O5—C21—C22—O616.2 (3)C11—C16—C11'—C1'148 (7)
O4—C21—C22—C2313.2 (3)C17—C16—C11'—N1'134.5 (6)
O5—C21—C22—C23134.1 (2)C15—C16—C11'—N1'10.5 (8)
O6—C22—C23—O8166.06 (18)C11—C16—C11'—N1'91 (6)
C21—C22—C23—O878.4 (3)C10'—C11'—C1'—C2'177 (2)
O6—C22—C23—C2478.2 (2)N1'—C11'—C1'—C2'57 (2)
C21—C22—C23—C2437.3 (3)C16—C11'—C1'—C2'64 (3)
O4—C20—C24—O774.5 (2)C10'—C11'—C1'—C12'7.6 (19)
C15—C20—C24—O747.7 (3)N1'—C11'—C1'—C12'128.1 (14)
O4—C20—C24—C2341.7 (2)C16—C11'—C1'—C12'111.2 (16)
C15—C20—C24—C23163.89 (19)C12'—C1'—C2'—C3'2 (2)
O8—C23—C24—O711.9 (2)C11'—C1'—C2'—C3'177.6 (18)
C22—C23—C24—O7129.3 (2)C1'—C2'—C3'—C4'5.6 (18)
O8—C23—C24—C20108.4 (2)C2'—C3'—C4'—C5'5.0 (15)
C22—C23—C24—C209.0 (3)C3'—C4'—C5'—C6'177.7 (12)
O5—C21—O4—C2076.6 (2)C3'—C4'—C5'—C12'1.4 (14)
C22—C21—O4—C2040.9 (3)C4'—C5'—C6'—C7'177.2 (9)
C24—C20—O4—C2170.7 (2)C12'—C5'—C6'—C7'1.9 (18)
C15—C20—O4—C21161.89 (17)C5'—C6'—C7'—C8'0.2 (17)
O4—C21—O5—C25132.1 (5)C6'—C7'—C8'—C9'2.6 (15)
C22—C21—O5—C258.8 (5)C7'—C8'—C9'—C12'3 (2)
O4—C21—O5—C25'111.7 (10)C7'—C8'—C9'—C10'177.9 (19)
C22—C21—O5—C25'11.6 (10)C6'—C5'—C12'—C9'2 (2)
C23—C22—O6—C25157.0 (4)C4'—C5'—C12'—C9'177.5 (16)
C21—C22—O6—C2534.6 (5)C6'—C5'—C12'—C1'178.9 (17)
C23—C22—O6—C25'138.5 (9)C4'—C5'—C12'—C1'2 (2)
C21—C22—O6—C25'16.1 (10)C8'—C9'—C12'—C5'1 (3)
O8—C28—O7—C2426.9 (3)C10'—C9'—C12'—C5'179.8 (16)
C30—C28—O7—C24142.4 (11)C8'—C9'—C12'—C1'178.9 (16)
C30'—C28—O7—C24141.7 (17)C10'—C9'—C12'—C1'1 (2)
C29'—C28—O7—C2496 (2)C2'—C1'—C12'—C5'1 (3)
C29—C28—O7—C2489.8 (10)C11'—C1'—C12'—C5'175.0 (17)
C20—C24—O7—C28130.0 (2)C2'—C1'—C12'—C9'178.1 (17)
C23—C24—O7—C289.2 (2)C11'—C1'—C12'—C9'6 (2)
C22—C23—O8—C28151.80 (19)C8'—C9'—C10'—O1'5 (3)
C24—C23—O8—C2828.5 (2)C12'—C9'—C10'—O1'174.4 (19)
O7—C28—O8—C2334.8 (2)C8'—C9'—C10'—C11'176 (2)
C30—C28—O8—C23156.3 (11)C12'—C9'—C10'—C11'4 (2)
C30'—C28—O8—C23141 (2)C1'—C11'—C10'—O1'171.6 (18)
C29'—C28—O8—C2394 (2)N1'—C11'—C10'—O1'58 (2)
C29—C28—O8—C2378.5 (12)C16—C11'—C10'—O1'58 (2)
C17—C16—C11—N1161.8 (4)C1'—C11'—C10'—C9'7 (2)
C15—C16—C11—N131.4 (7)N1'—C11'—C10'—C9'120.7 (15)
C11'—C16—C11—N1113 (7)C16—C11'—C10'—C9'123.1 (15)
C17—C16—C11—C134.8 (12)N1—C14—N1'—C11'65.4 (6)
C15—C16—C11—C195.6 (10)C15—C14—N1'—C11'36.3 (7)
C11'—C16—C11—C114 (6)N1—C14—N1'—C13'52.9 (8)
C17—C16—C11—C1081.5 (9)C15—C14—N1'—C13'154.6 (7)
C15—C16—C11—C10148.1 (8)C10'—C11'—N1'—C14101.7 (9)
C11'—C16—C11—C10130 (7)C1'—C11'—N1'—C14148.0 (8)
N1—C11—C1—C251 (2)C16—C11'—N1'—C1415.7 (9)
C10—C11—C1—C2174.5 (17)C10'—C11'—N1'—C13'12.3 (12)
C16—C11—C1—C262 (2)C1'—C11'—N1'—C13'98.0 (11)
N1—C11—C1—C12125.4 (12)C16—C11'—N1'—C13'129.7 (8)
C10—C11—C1—C122.3 (17)O2—C17—O3'—C18'7 (2)
C16—C11—C1—C12120.8 (13)O2'—C17—O3'—C18'17 (2)
C12—C1—C2—C33.6 (19)O3—C17—O3'—C18'95 (10)
C11—C1—C2—C3179.9 (15)C16—C17—O3'—C18'179.2 (12)
C1—C2—C3—C40.6 (13)C17—O3'—C18'—C19'136.3 (18)
C2—C3—C4—C52.0 (13)C21—O5—C25—O630.3 (7)
C3—C4—C5—C6179.6 (8)C25'—O5—C25—O678.6 (14)
C3—C4—C5—C121.5 (15)C21—O5—C25—C26141.9 (6)
C4—C5—C6—C7179.5 (11)C25'—O5—C25—C2633.1 (14)
C12—C5—C6—C71.4 (15)C21—O5—C25—C2794.9 (5)
C5—C6—C7—C80.2 (19)C25'—O5—C25—C27156.3 (17)
C6—C7—C8—C91.2 (19)C22—O6—C25—O540.5 (7)
C7—C8—C9—C121 (2)C25'—O6—C25—O578.8 (14)
C7—C8—C9—C10178.7 (18)C22—O6—C25—C26152.2 (6)
C2—C1—C12—C54 (2)C25'—O6—C25—C2633.0 (15)
C11—C1—C12—C5178.5 (15)C22—O6—C25—C2781.9 (5)
C2—C1—C12—C9176.9 (15)C25'—O6—C25—C27158.8 (17)
C11—C1—C12—C91 (2)C21—O5—C25'—O62.3 (15)
C6—C5—C12—C1176.8 (14)C25—O5—C25'—O676.2 (14)
C4—C5—C12—C12 (2)C21—O5—C25'—C26'129.7 (9)
C6—C5—C12—C92 (2)C25—O5—C25'—C26'152 (2)
C4—C5—C12—C9179.6 (15)C21—O5—C25'—C27'105.7 (10)
C8—C9—C12—C1177.8 (15)C25—O5—C25'—C27'27.2 (15)
C10—C9—C12—C12 (2)C22—O6—C25'—O59.3 (15)
C8—C9—C12—C51 (3)C25—O6—C25'—O575.9 (13)
C10—C9—C12—C5179.4 (14)C22—O6—C25'—C26'140.9 (11)
C8—C9—C10—O10 (3)C25—O6—C25'—C26'153 (2)
C12—C9—C10—O1179.1 (15)C22—O6—C25'—C27'99.9 (10)
C8—C9—C10—C11176.3 (17)C25—O6—C25'—C27'33.3 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O1i0.982.453.324 (7)148
Symmetry code: (i) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O1i0.982.453.324 (7)148.2
Symmetry code: (i) x1/2, y+1/2, z+1.
Acknowledgements top

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection. KS thanks the University Grant Commission (UGC), India, for a Minor Research Project.

references
References top

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature. 437, 209–214.

Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012). Acta Cryst. E68, o2505–o2506.

Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820–5824.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.