supplementary materials


lh5596 scheme

Acta Cryst. (2013). E69, o746-o747    [ doi:10.1107/S1600536813009987 ]

4'-(4-Fluorophenyl)-1'-methyldispiro[indane-2,2'-pyrrolidine-3',2''-indane]-1,3,1''-trione methanol hemisolvate

M. A. Ali, E. Manogaran, T. S. Choon, M. M. Rosli and I. A. Razak

Abstract top

The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent molecules and a one methanol solvent molecule. The methanol molecule is O-H...O hydrogen bonded to one of the independent molecules. The pyrrolidine rings in both molecules adopt half-chair conformations, while the cyclopentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent molecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one molecule, and 72.78 (8) and 77.27 (8)° in the other. In each molecule, a weak intramolecular C-H...O hydrogen bond forms an S(6) ring motif. In the crystal, weak C-H...O, C-H...N and C-H...F hydrogen bonds link the molecules into a three-dimensional network.

Comment top

Tuberculosis (TB) remains a global health problem and has infected about one third of the world population. No new drugs have been discovered for the past 40 years and therefore new anti-TB agents are desperately needed (Ali et al., 2011). As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei et al., 2011, 2012) the crystal structure of the title compound (I) has been determined.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules and a molecule of methanol (Fig. 1). In both molecules, the intramolecular interactions of C8A—H8AA···O5A and C8B—H8BA···O5B (Table 1) form an S(6) ring motif (Fig. 2) (Bernstein et al. 1995). The pyrrolidine ring for both molecules A and B adopt a half-chair conformation with the puckering parameters Q = 0.4612 (16) Å, φ = 127.36 (19)° for molecule A and Q = 0.4332 (16) Å, φ = 125.2 (2)° for molecule B. In both molecules, A and B, the cyclopentane rings (C1—C2/C7—C9 & C12—C14/C19—C20) within the indane moiety (C1—C9 & C12—C20) form flattened envelope conformations (C9 and C12 at the flap) with the puckering parameters Q = 0.1587 (16) Å, φ 146.2 (6)° and Q = 0.1910 (16) Å, φ = 175.0 (5)° for molecule A and Q = 0.1338 (15)å, φ = 155.5 (6)° and Q = 0.2232 (16) Å, φ = 173.6 (4)° for molecule B.

In each molecule, the benzene rings of the indane ring systems form dihedral angles of 35.06 (7) ° [C2A-C7A/C14A-C19A] and 31.16 (8)° [C2B-C7B/C14B-C19B] with each other. The fluoro-substituted benzene ring forms diedral angles of 65.35 (6)° [C14A-C19A/C21A-C26A] and 85.87 (7)° [C2A-C7A/C21A-C26A] with the indane group benzene rings of one molecule and 72.78 (8)° [C14B-C19B/C21B-C26B] and 77.27 (8)° [C2B-C7B/C21B-C26B] in the other.

In the crystal, molecules are connected by weak C—H···Oi, iii, iv, C—H···Nii and C—H···Fv (Table 1) hydrogen bonds into a three-dimensional network (Fig. 3).

Related literature top

For background to compounds with antitubercular activity, see: Ali et al. (2011). For related structures, see: Wei et al. (2011, 2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 5,6-dimethoxy(E)-2-(4-fluorobenzylidene)-2,3-dihydro-1H-indene-1-one (0.001 mol), ninhydrin (0.001 mol) and sarcosine (0.002 mol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the excess solvent was evaporated slowly and the product was separated and recrystallized from methanol to reveal the title compound as yellow crystals.

Refinement top

O bound H atoms were located from a difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C-methyl).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecule A of the title compound, showing 50% probability displacement ellipsoids. The dashed lines indicate hydrogen bonds. The solvent molecule is also shown.
[Figure 2] Fig. 2. Molecule B of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a weak hydrogen bond.
[Figure 3] Fig. 3. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
4'-(4-Fluorophenyl)-1'-methyldispiro[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione methanol hemisolvate top
Crystal data top
C29H24FNO5·0.5CH4OF(000) = 2104
Mr = 501.52Dx = 1.390 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9905 reflections
a = 14.6385 (6) Åθ = 2.3–30.1°
b = 12.5099 (6) ŵ = 0.10 mm1
c = 26.2017 (10) ÅT = 100 K
β = 92.645 (1)°Block, yellow
V = 4793.1 (4) Å30.44 × 0.21 × 0.15 mm
Z = 8
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
14094 independent reflections
Radiation source: fine-focus sealed tube10283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 30.2°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2019
Tmin = 0.957, Tmax = 0.985k = 1717
53390 measured reflectionsl = 3737
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0784P)2 + 0.9156P]
where P = (Fo2 + 2Fc2)/3
14094 reflections(Δ/σ)max = 0.001
678 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C29H24FNO5·0.5CH4OV = 4793.1 (4) Å3
Mr = 501.52Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.6385 (6) ŵ = 0.10 mm1
b = 12.5099 (6) ÅT = 100 K
c = 26.2017 (10) Å0.44 × 0.21 × 0.15 mm
β = 92.645 (1)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
14094 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
10283 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.985Rint = 0.046
53390 measured reflectionsθmax = 30.2°
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147Δρmax = 0.40 e Å3
S = 1.04Δρmin = 0.27 e Å3
14094 reflectionsAbsolute structure: ?
678 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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*/Ueq
F1A0.64124 (8)0.50699 (10)1.07056 (4)0.0408 (3)
O1A0.57712 (7)0.75263 (10)0.83001 (4)0.0224 (2)
O2A0.90976 (7)0.94421 (10)0.81133 (4)0.0217 (2)
O3A0.92179 (7)1.05466 (10)0.89424 (4)0.0230 (2)
O4A0.36455 (7)0.82926 (10)0.82207 (4)0.0235 (2)
O5A0.52744 (8)1.12958 (10)0.87961 (4)0.0297 (3)
N1A0.40617 (8)0.96181 (12)0.91618 (4)0.0213 (3)
C1A0.60138 (9)0.82167 (13)0.86036 (5)0.0169 (3)
C2A0.68848 (9)0.87866 (12)0.86443 (5)0.0159 (3)
C3A0.75949 (9)0.87575 (13)0.83026 (5)0.0166 (3)
H3AA0.75490.83250.80050.020*
C4A0.83602 (9)0.93716 (13)0.84103 (5)0.0170 (3)
C5A0.84241 (9)0.99947 (13)0.88693 (5)0.0179 (3)
C6A0.77115 (9)1.00136 (13)0.92012 (5)0.0190 (3)
H6AA0.77561.04290.95050.023*
C7A0.69312 (9)0.94131 (13)0.90805 (5)0.0168 (3)
C8A0.60674 (9)0.93285 (14)0.93741 (5)0.0199 (3)
H8AA0.58201.00460.94490.024*
H8AB0.61830.89390.96990.024*
C9A0.54029 (9)0.86988 (13)0.90093 (5)0.0177 (3)
C10A0.47557 (9)0.78925 (13)0.92612 (5)0.0186 (3)
H10A0.45090.74140.89820.022*
C11A0.39533 (10)0.85875 (14)0.94223 (5)0.0230 (3)
H11A0.33620.82520.93160.028*
H11B0.39760.86860.97980.028*
C12A0.46681 (9)0.94658 (13)0.87478 (5)0.0188 (3)
C13A0.42549 (9)0.89548 (13)0.82479 (5)0.0187 (3)
C14A0.46926 (9)0.94764 (13)0.78149 (5)0.0192 (3)
C15A0.46305 (10)0.92065 (14)0.72959 (5)0.0225 (3)
H15A0.42940.86000.71770.027*
C16A0.50824 (11)0.98630 (15)0.69640 (6)0.0265 (3)
H16A0.50480.97070.66090.032*
C17A0.55860 (11)1.07468 (15)0.71386 (6)0.0283 (4)
H17A0.58881.11770.69000.034*
C18A0.56576 (11)1.10154 (14)0.76558 (6)0.0251 (3)
H18A0.60051.16140.77750.030*
C19A0.51950 (10)1.03640 (13)0.79895 (5)0.0203 (3)
C20A0.50932 (10)1.05031 (14)0.85470 (5)0.0213 (3)
C21A0.52098 (9)0.71733 (13)0.96626 (5)0.0194 (3)
C22A0.56305 (10)0.62396 (14)0.95030 (5)0.0228 (3)
H22A0.56300.60820.91480.027*
C23A0.60491 (11)0.55361 (15)0.98488 (6)0.0280 (3)
H23A0.63380.49050.97350.034*
C24A0.60348 (11)0.57771 (15)1.03629 (6)0.0264 (3)
C25A0.56456 (11)0.66976 (15)1.05385 (6)0.0266 (3)
H25A0.56580.68531.08940.032*
C26A0.52338 (10)0.73952 (14)1.01870 (5)0.0232 (3)
H26A0.49630.80351.03040.028*
C27A0.90161 (11)0.88598 (15)0.76404 (5)0.0241 (3)
H27A0.95850.89270.74600.036*
H27B0.85080.91510.74270.036*
H27C0.89000.81040.77110.036*
C28A0.94184 (11)1.09428 (14)0.94499 (5)0.0241 (3)
H28A1.00311.12620.94680.036*
H28B0.93961.03520.96940.036*
H28C0.89661.14850.95330.036*
C29A0.32106 (11)1.01814 (16)0.90408 (6)0.0301 (4)
H29A0.33441.08730.88850.045*
H29B0.28851.02960.93550.045*
H29C0.28290.97540.88010.045*
F1B0.73958 (9)0.84660 (11)0.64602 (4)0.0508 (3)
O1B0.70176 (7)0.52113 (10)0.86215 (4)0.0209 (2)
O2B0.87193 (7)0.80278 (10)0.99446 (3)0.0214 (2)
O3B1.01505 (7)0.84762 (9)0.94574 (4)0.0201 (2)
O4B0.72154 (7)0.27525 (10)0.83132 (4)0.0265 (2)
O5B1.01994 (7)0.37946 (11)0.87438 (4)0.0271 (3)
N1B0.89700 (8)0.33138 (11)0.78465 (4)0.0196 (3)
C1B0.78116 (9)0.54550 (12)0.85591 (4)0.0152 (3)
C2B0.83736 (9)0.62300 (12)0.88429 (5)0.0147 (3)
C3B0.81686 (9)0.67684 (13)0.92947 (5)0.0163 (3)
H3BA0.76100.66420.94550.020*
C4B0.88014 (9)0.74835 (12)0.94969 (4)0.0162 (3)
C5B0.96145 (9)0.77097 (12)0.92353 (5)0.0163 (3)
C6B0.98171 (9)0.71501 (12)0.87953 (5)0.0161 (3)
H6BA1.03680.72830.86280.019*
C7B0.91913 (9)0.63893 (12)0.86061 (5)0.0147 (3)
C8B0.92686 (9)0.56662 (12)0.81472 (5)0.0162 (3)
H8BA0.98380.52390.81760.019*
H8BB0.92640.60870.78270.019*
C9B0.84145 (9)0.49360 (12)0.81595 (5)0.0152 (3)
C10B0.79019 (9)0.47193 (13)0.76358 (5)0.0171 (3)
H10B0.72750.44670.77130.021*
C11B0.84021 (11)0.37537 (15)0.74183 (5)0.0246 (3)
H11C0.79580.32130.72850.030*
H11D0.87890.39780.71370.030*
C12B0.86621 (9)0.37560 (13)0.83180 (5)0.0168 (3)
C13B0.78331 (10)0.31936 (13)0.85524 (5)0.0195 (3)
C14B0.79773 (10)0.32678 (13)0.91197 (5)0.0217 (3)
C15B0.73581 (12)0.30775 (15)0.94960 (6)0.0293 (4)
H15B0.67580.28240.94130.035*
C16B0.76572 (14)0.32748 (16)1.00007 (6)0.0356 (4)
H16B0.72480.31651.02670.043*
C17B0.85401 (14)0.36275 (16)1.01225 (6)0.0349 (4)
H17B0.87200.37631.04700.042*
C18B0.91653 (12)0.37851 (15)0.97473 (5)0.0285 (4)
H18B0.97760.40020.98310.034*
C19B0.88584 (10)0.36111 (13)0.92418 (5)0.0211 (3)
C20B0.93768 (10)0.37345 (13)0.87703 (5)0.0190 (3)
C21B0.77768 (10)0.57045 (13)0.73034 (5)0.0180 (3)
C22B0.70115 (10)0.63458 (14)0.73650 (5)0.0215 (3)
H22B0.65760.61440.76050.026*
C23B0.68725 (12)0.72781 (15)0.70811 (6)0.0289 (4)
H23B0.63450.77080.71210.035*
C24B0.75230 (13)0.75584 (15)0.67412 (6)0.0332 (4)
C25B0.82992 (12)0.69646 (16)0.66743 (5)0.0303 (4)
H25B0.87390.71870.64410.036*
C26B0.84227 (10)0.60341 (15)0.69561 (5)0.0236 (3)
H26B0.89530.56120.69140.028*
C27B0.80001 (11)0.76736 (16)1.02551 (5)0.0270 (4)
H27D0.80310.80651.05790.041*
H27E0.80690.69061.03220.041*
H27F0.74080.78071.00760.041*
C28B1.09083 (10)0.88541 (14)0.91793 (6)0.0246 (3)
H28D1.11960.94600.93610.037*
H28E1.06900.90820.88370.037*
H28F1.13560.82780.91500.037*
C29B0.91046 (12)0.21643 (14)0.78356 (6)0.0261 (3)
H29D0.94980.19480.81300.039*
H29E0.93950.19650.75200.039*
H29F0.85120.18040.78490.039*
O60.22217 (10)0.69772 (12)0.86621 (5)0.0390 (3)
C300.21176 (13)0.59596 (17)0.84332 (7)0.0352 (4)
H30A0.15910.55950.85720.053*
H30B0.26710.55350.85060.053*
H30C0.20190.60420.80630.053*
H1O60.277 (2)0.733 (3)0.8553 (10)0.072 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0473 (6)0.0336 (7)0.0402 (5)0.0073 (5)0.0137 (5)0.0095 (5)
O1A0.0207 (5)0.0232 (6)0.0233 (5)0.0028 (4)0.0017 (4)0.0061 (4)
O2A0.0180 (5)0.0276 (7)0.0198 (4)0.0052 (4)0.0042 (3)0.0008 (4)
O3A0.0200 (5)0.0278 (7)0.0209 (4)0.0085 (5)0.0032 (4)0.0018 (4)
O4A0.0189 (5)0.0248 (6)0.0268 (5)0.0033 (5)0.0000 (4)0.0022 (4)
O5A0.0339 (6)0.0223 (7)0.0331 (5)0.0023 (5)0.0060 (5)0.0066 (5)
N1A0.0189 (6)0.0227 (7)0.0229 (5)0.0055 (5)0.0067 (4)0.0016 (5)
C1A0.0153 (6)0.0192 (8)0.0163 (5)0.0008 (6)0.0012 (4)0.0002 (5)
C2A0.0143 (6)0.0167 (7)0.0168 (5)0.0009 (5)0.0003 (4)0.0005 (5)
C3A0.0166 (6)0.0176 (7)0.0157 (5)0.0013 (5)0.0007 (4)0.0012 (5)
C4A0.0149 (6)0.0189 (8)0.0171 (5)0.0003 (5)0.0009 (4)0.0017 (5)
C5A0.0169 (6)0.0175 (8)0.0189 (5)0.0025 (6)0.0030 (5)0.0011 (5)
C6A0.0199 (6)0.0189 (8)0.0179 (5)0.0004 (6)0.0016 (5)0.0029 (5)
C7A0.0154 (6)0.0187 (8)0.0162 (5)0.0020 (6)0.0005 (4)0.0005 (5)
C8A0.0179 (6)0.0231 (8)0.0187 (5)0.0001 (6)0.0021 (5)0.0046 (5)
C9A0.0147 (6)0.0209 (8)0.0178 (5)0.0014 (6)0.0031 (4)0.0014 (5)
C10A0.0164 (6)0.0212 (8)0.0184 (5)0.0000 (6)0.0024 (4)0.0002 (5)
C11A0.0195 (6)0.0270 (9)0.0230 (6)0.0040 (6)0.0063 (5)0.0044 (6)
C12A0.0165 (6)0.0203 (8)0.0199 (6)0.0020 (6)0.0041 (5)0.0004 (5)
C13A0.0156 (6)0.0188 (8)0.0218 (6)0.0020 (6)0.0022 (5)0.0028 (5)
C14A0.0166 (6)0.0197 (8)0.0215 (6)0.0026 (6)0.0023 (5)0.0030 (5)
C15A0.0214 (7)0.0236 (9)0.0226 (6)0.0046 (6)0.0006 (5)0.0017 (6)
C16A0.0268 (7)0.0305 (10)0.0226 (6)0.0064 (7)0.0040 (5)0.0048 (6)
C17A0.0262 (7)0.0288 (10)0.0305 (7)0.0042 (7)0.0089 (6)0.0118 (7)
C18A0.0228 (7)0.0200 (9)0.0328 (7)0.0009 (6)0.0041 (6)0.0032 (6)
C19A0.0179 (6)0.0187 (8)0.0245 (6)0.0037 (6)0.0030 (5)0.0013 (6)
C20A0.0182 (6)0.0191 (8)0.0266 (6)0.0027 (6)0.0036 (5)0.0004 (6)
C21A0.0168 (6)0.0210 (8)0.0204 (6)0.0007 (6)0.0021 (5)0.0011 (5)
C22A0.0210 (7)0.0243 (9)0.0232 (6)0.0001 (6)0.0026 (5)0.0029 (6)
C23A0.0248 (7)0.0234 (9)0.0356 (8)0.0026 (7)0.0002 (6)0.0019 (7)
C24A0.0236 (7)0.0252 (9)0.0298 (7)0.0006 (7)0.0040 (6)0.0069 (6)
C25A0.0272 (7)0.0306 (10)0.0220 (6)0.0000 (7)0.0012 (5)0.0016 (6)
C26A0.0253 (7)0.0244 (9)0.0201 (6)0.0029 (7)0.0034 (5)0.0013 (6)
C27A0.0239 (7)0.0297 (9)0.0193 (6)0.0036 (7)0.0068 (5)0.0014 (6)
C28A0.0241 (7)0.0224 (9)0.0249 (6)0.0032 (6)0.0077 (5)0.0046 (6)
C29A0.0239 (7)0.0332 (11)0.0338 (8)0.0120 (7)0.0092 (6)0.0071 (7)
F1B0.0692 (8)0.0313 (7)0.0496 (6)0.0141 (6)0.0230 (6)0.0227 (5)
O1B0.0152 (4)0.0251 (6)0.0226 (4)0.0025 (4)0.0032 (3)0.0027 (4)
O2B0.0222 (5)0.0258 (6)0.0163 (4)0.0008 (5)0.0024 (3)0.0082 (4)
O3B0.0190 (5)0.0203 (6)0.0212 (4)0.0058 (4)0.0014 (3)0.0047 (4)
O4B0.0228 (5)0.0242 (7)0.0325 (5)0.0055 (5)0.0006 (4)0.0008 (5)
O5B0.0192 (5)0.0313 (7)0.0305 (5)0.0025 (5)0.0009 (4)0.0025 (5)
N1B0.0228 (6)0.0196 (7)0.0167 (5)0.0028 (5)0.0027 (4)0.0037 (5)
C1B0.0147 (6)0.0165 (7)0.0146 (5)0.0004 (5)0.0011 (4)0.0012 (5)
C2B0.0150 (6)0.0147 (7)0.0144 (5)0.0001 (5)0.0013 (4)0.0006 (5)
C3B0.0147 (6)0.0184 (8)0.0159 (5)0.0015 (5)0.0025 (4)0.0008 (5)
C4B0.0181 (6)0.0165 (7)0.0138 (5)0.0024 (5)0.0008 (4)0.0020 (5)
C5B0.0167 (6)0.0156 (7)0.0164 (5)0.0018 (5)0.0015 (4)0.0001 (5)
C6B0.0159 (6)0.0167 (7)0.0159 (5)0.0010 (5)0.0026 (4)0.0000 (5)
C7B0.0149 (6)0.0149 (7)0.0142 (5)0.0001 (5)0.0014 (4)0.0004 (5)
C8B0.0156 (6)0.0172 (7)0.0159 (5)0.0025 (5)0.0032 (4)0.0024 (5)
C9B0.0150 (6)0.0153 (7)0.0155 (5)0.0011 (5)0.0019 (4)0.0022 (5)
C10B0.0184 (6)0.0170 (8)0.0160 (5)0.0020 (6)0.0004 (4)0.0026 (5)
C11B0.0308 (8)0.0253 (9)0.0175 (6)0.0058 (7)0.0025 (5)0.0066 (6)
C12B0.0165 (6)0.0176 (8)0.0165 (5)0.0003 (6)0.0018 (4)0.0018 (5)
C13B0.0188 (6)0.0177 (8)0.0221 (6)0.0013 (6)0.0033 (5)0.0010 (5)
C14B0.0262 (7)0.0172 (8)0.0223 (6)0.0033 (6)0.0057 (5)0.0027 (6)
C15B0.0337 (8)0.0252 (9)0.0298 (7)0.0049 (7)0.0115 (6)0.0092 (7)
C16B0.0518 (11)0.0295 (10)0.0269 (7)0.0137 (9)0.0181 (7)0.0110 (7)
C17B0.0586 (12)0.0276 (10)0.0184 (6)0.0126 (9)0.0022 (7)0.0034 (6)
C18B0.0405 (9)0.0243 (9)0.0200 (6)0.0078 (7)0.0044 (6)0.0006 (6)
C19B0.0289 (7)0.0162 (8)0.0183 (6)0.0059 (6)0.0014 (5)0.0019 (5)
C20B0.0189 (6)0.0180 (8)0.0200 (6)0.0019 (6)0.0002 (5)0.0027 (5)
C21B0.0209 (6)0.0181 (8)0.0148 (5)0.0034 (6)0.0017 (4)0.0022 (5)
C22B0.0224 (7)0.0202 (8)0.0215 (6)0.0024 (6)0.0019 (5)0.0016 (6)
C23B0.0337 (8)0.0184 (9)0.0334 (7)0.0004 (7)0.0112 (6)0.0002 (6)
C24B0.0471 (10)0.0220 (9)0.0288 (7)0.0124 (8)0.0166 (7)0.0098 (7)
C25B0.0365 (9)0.0349 (11)0.0191 (6)0.0173 (8)0.0046 (6)0.0044 (6)
C26B0.0242 (7)0.0312 (10)0.0155 (5)0.0076 (7)0.0002 (5)0.0017 (6)
C27B0.0257 (7)0.0367 (11)0.0193 (6)0.0002 (7)0.0067 (5)0.0064 (6)
C28B0.0212 (7)0.0237 (9)0.0291 (7)0.0072 (6)0.0040 (5)0.0031 (6)
C29B0.0307 (8)0.0212 (9)0.0267 (7)0.0043 (7)0.0023 (6)0.0046 (6)
O60.0455 (8)0.0322 (8)0.0409 (7)0.0065 (6)0.0185 (6)0.0034 (6)
C300.0367 (9)0.0344 (11)0.0346 (8)0.0034 (8)0.0009 (7)0.0008 (8)
Geometric parameters (Å, º) top
F1A—C24A1.3597 (19)O2B—C27B1.4302 (18)
O1A—C1A1.2158 (18)O3B—C5B1.3534 (17)
O2A—C4A1.3624 (16)O3B—C28B1.4351 (18)
O2A—C27A1.4376 (18)O4B—C13B1.2093 (18)
O3A—C5A1.3575 (17)O5B—C20B1.2116 (18)
O3A—C28A1.4366 (17)N1B—C12B1.4446 (17)
O4A—C13A1.2170 (19)N1B—C29B1.452 (2)
O5A—C20A1.210 (2)N1B—C11B1.4719 (18)
N1A—C12A1.4455 (17)C1B—C2B1.4538 (19)
N1A—C29A1.453 (2)C1B—C9B1.5433 (18)
N1A—C11A1.471 (2)C2B—C7B1.3877 (18)
C1A—C2A1.4604 (19)C2B—C3B1.4064 (18)
C1A—C9A1.5432 (18)C3B—C4B1.376 (2)
C2A—C7A1.3848 (19)C3B—H3BA0.9500
C2A—C3A1.4034 (18)C4B—C5B1.4290 (19)
C3A—C4A1.377 (2)C5B—C6B1.3924 (18)
C3A—H3AA0.9500C6B—C7B1.396 (2)
C4A—C5A1.4326 (19)C6B—H6BA0.9500
C5A—C6A1.3888 (19)C7B—C8B1.5132 (18)
C6A—C7A1.391 (2)C8B—C9B1.5499 (19)
C6A—H6AA0.9500C8B—H8BA0.9900
C7A—C8A1.5138 (19)C8B—H8BB0.9900
C8A—C9A1.547 (2)C9B—C10B1.5570 (17)
C8A—H8AA0.9900C9B—C12B1.571 (2)
C8A—H8AB0.9900C10B—C21B1.515 (2)
C9A—C10A1.552 (2)C10B—C11B1.536 (2)
C9A—C12A1.575 (2)C10B—H10B1.0000
C10A—C21A1.514 (2)C11B—H11C0.9900
C10A—C11A1.536 (2)C11B—H11D0.9900
C10A—H10A1.0000C12B—C20B1.5446 (18)
C11A—H11A0.9900C12B—C13B1.554 (2)
C11A—H11B0.9900C13B—C14B1.4944 (19)
C12A—C20A1.542 (2)C14B—C19B1.383 (2)
C12A—C13A1.555 (2)C14B—C15B1.390 (2)
C13A—C14A1.4801 (19)C15B—C16B1.396 (2)
C14A—C19A1.397 (2)C15B—H15B0.9500
C14A—C15A1.4000 (19)C16B—C17B1.389 (3)
C15A—C16A1.386 (2)C16B—H16B0.9500
C15A—H15A0.9500C17B—C18B1.388 (2)
C16A—C17A1.394 (3)C17B—H17B0.9500
C16A—H16A0.9500C18B—C19B1.3959 (19)
C17A—C18A1.395 (2)C18B—H18B0.9500
C17A—H17A0.9500C19B—C20B1.4874 (19)
C18A—C19A1.393 (2)C21B—C22B1.393 (2)
C18A—H18A0.9500C21B—C26B1.404 (2)
C19A—C20A1.4853 (19)C22B—C23B1.393 (2)
C21A—C22A1.394 (2)C22B—H22B0.9500
C21A—C26A1.4004 (19)C23B—C24B1.379 (3)
C22A—C23A1.385 (2)C23B—H23B0.9500
C22A—H22A0.9500C24B—C25B1.375 (3)
C23A—C24A1.382 (2)C25B—C26B1.386 (2)
C23A—H23A0.9500C25B—H25B0.9500
C24A—C25A1.373 (3)C26B—H26B0.9500
C25A—C26A1.386 (2)C27B—H27D0.9800
C25A—H25A0.9500C27B—H27E0.9800
C26A—H26A0.9500C27B—H27F0.9800
C27A—H27A0.9800C28B—H28D0.9800
C27A—H27B0.9800C28B—H28E0.9800
C27A—H27C0.9800C28B—H28F0.9800
C28A—H28A0.9800C29B—H29D0.9800
C28A—H28B0.9800C29B—H29E0.9800
C28A—H28C0.9800C29B—H29F0.9800
C29A—H29A0.9800O6—C301.412 (2)
C29A—H29B0.9800O6—H1O60.97 (3)
C29A—H29C0.9800C30—H30A0.9800
F1B—C24B1.361 (2)C30—H30B0.9800
O1B—C1B1.2199 (16)C30—H30C0.9800
O2B—C4B1.3666 (15)
C4A—O2A—C27A115.02 (11)C29B—N1B—C11B115.32 (12)
C5A—O3A—C28A116.30 (11)O1B—C1B—C2B128.19 (12)
C12A—N1A—C29A116.75 (12)O1B—C1B—C9B124.33 (13)
C12A—N1A—C11A108.41 (12)C2B—C1B—C9B107.44 (11)
C29A—N1A—C11A114.61 (13)C7B—C2B—C3B121.97 (12)
O1A—C1A—C2A128.48 (12)C7B—C2B—C1B110.27 (11)
O1A—C1A—C9A124.55 (13)C3B—C2B—C1B127.75 (12)
C2A—C1A—C9A106.89 (12)C4B—C3B—C2B117.99 (12)
C7A—C2A—C3A122.12 (13)C4B—C3B—H3BA121.0
C7A—C2A—C1A110.24 (12)C2B—C3B—H3BA121.0
C3A—C2A—C1A127.63 (12)O2B—C4B—C3B124.76 (12)
C4A—C3A—C2A118.32 (12)O2B—C4B—C5B114.92 (12)
C4A—C3A—H3AA120.8C3B—C4B—C5B120.32 (12)
C2A—C3A—H3AA120.8O3B—C5B—C6B124.81 (12)
O2A—C4A—C3A125.29 (12)O3B—C5B—C4B114.41 (11)
O2A—C4A—C5A114.93 (12)C6B—C5B—C4B120.77 (13)
C3A—C4A—C5A119.78 (12)C5B—C6B—C7B118.38 (12)
O3A—C5A—C6A124.46 (13)C5B—C6B—H6BA120.8
O3A—C5A—C4A114.67 (12)C7B—C6B—H6BA120.8
C6A—C5A—C4A120.87 (13)C2B—C7B—C6B120.30 (12)
C5A—C6A—C7A118.75 (13)C2B—C7B—C8B111.54 (12)
C5A—C6A—H6AA120.6C6B—C7B—C8B128.16 (12)
C7A—C6A—H6AA120.6C7B—C8B—C9B104.23 (10)
C2A—C7A—C6A120.11 (12)C7B—C8B—H8BA110.9
C2A—C7A—C8A111.69 (12)C9B—C8B—H8BA110.9
C6A—C7A—C8A128.20 (12)C7B—C8B—H8BB110.9
C7A—C8A—C9A103.75 (10)C9B—C8B—H8BB110.9
C7A—C8A—H8AA111.0H8BA—C8B—H8BB108.9
C9A—C8A—H8AA111.0C1B—C9B—C8B104.67 (11)
C7A—C8A—H8AB111.0C1B—C9B—C10B113.81 (11)
C9A—C8A—H8AB111.0C8B—C9B—C10B116.14 (11)
H8AA—C8A—H8AB109.0C1B—C9B—C12B110.37 (11)
C1A—C9A—C8A104.88 (11)C8B—C9B—C12B112.50 (11)
C1A—C9A—C10A115.06 (13)C10B—C9B—C12B99.51 (11)
C8A—C9A—C10A116.55 (11)C21B—C10B—C11B118.27 (11)
C1A—C9A—C12A110.14 (10)C21B—C10B—C9B113.91 (12)
C8A—C9A—C12A110.85 (13)C11B—C10B—C9B104.20 (11)
C10A—C9A—C12A99.37 (11)C21B—C10B—H10B106.6
C21A—C10A—C11A117.53 (11)C11B—C10B—H10B106.6
C21A—C10A—C9A115.12 (11)C9B—C10B—H10B106.6
C11A—C10A—C9A103.80 (13)N1B—C11B—C10B105.86 (11)
C21A—C10A—H10A106.5N1B—C11B—H11C110.6
C11A—C10A—H10A106.5C10B—C11B—H11C110.6
C9A—C10A—H10A106.5N1B—C11B—H11D110.6
N1A—C11A—C10A105.57 (11)C10B—C11B—H11D110.6
N1A—C11A—H11A110.6H11C—C11B—H11D108.7
C10A—C11A—H11A110.6N1B—C12B—C20B114.99 (11)
N1A—C11A—H11B110.6N1B—C12B—C13B116.42 (12)
C10A—C11A—H11B110.6C20B—C12B—C13B101.69 (11)
H11A—C11A—H11B108.8N1B—C12B—C9B102.18 (10)
N1A—C12A—C20A114.62 (13)C20B—C12B—C9B111.04 (12)
N1A—C12A—C13A117.24 (12)C13B—C12B—C9B110.80 (11)
C20A—C12A—C13A101.88 (11)O4B—C13B—C14B127.71 (14)
N1A—C12A—C9A100.64 (10)O4B—C13B—C12B125.50 (12)
C20A—C12A—C9A112.52 (11)C14B—C13B—C12B106.74 (12)
C13A—C12A—C9A110.33 (12)C19B—C14B—C15B121.37 (14)
O4A—C13A—C14A126.67 (13)C19B—C14B—C13B109.69 (12)
O4A—C13A—C12A125.80 (12)C15B—C14B—C13B128.90 (15)
C14A—C13A—C12A107.41 (12)C14B—C15B—C16B117.09 (17)
C19A—C14A—C15A121.28 (14)C14B—C15B—H15B121.5
C19A—C14A—C13A109.84 (12)C16B—C15B—H15B121.5
C15A—C14A—C13A128.85 (15)C17B—C16B—C15B121.47 (15)
C16A—C15A—C14A117.07 (15)C17B—C16B—H16B119.3
C16A—C15A—H15A121.5C15B—C16B—H16B119.3
C14A—C15A—H15A121.5C18B—C17B—C16B121.29 (15)
C15A—C16A—C17A121.62 (14)C18B—C17B—H17B119.4
C15A—C16A—H16A119.2C16B—C17B—H17B119.4
C17A—C16A—H16A119.2C17B—C18B—C19B117.14 (16)
C16A—C17A—C18A121.63 (15)C17B—C18B—H18B121.4
C16A—C17A—H17A119.2C19B—C18B—H18B121.4
C18A—C17A—H17A119.2C14B—C19B—C18B121.59 (14)
C19A—C18A—C17A116.85 (16)C14B—C19B—C20B110.25 (12)
C19A—C18A—H18A121.6C18B—C19B—C20B128.15 (15)
C17A—C18A—H18A121.6O5B—C20B—C19B126.90 (13)
C18A—C19A—C14A121.54 (13)O5B—C20B—C12B126.49 (12)
C18A—C19A—C20A128.48 (15)C19B—C20B—C12B106.60 (11)
C14A—C19A—C20A109.87 (13)C22B—C21B—C26B118.36 (15)
O5A—C20A—C19A126.67 (15)C22B—C21B—C10B118.58 (12)
O5A—C20A—C12A125.97 (13)C26B—C21B—C10B122.96 (14)
C19A—C20A—C12A107.30 (13)C23B—C22B—C21B121.25 (15)
C22A—C21A—C26A117.97 (14)C23B—C22B—H22B119.4
C22A—C21A—C10A118.39 (12)C21B—C22B—H22B119.4
C26A—C21A—C10A123.64 (14)C24B—C23B—C22B118.00 (17)
C23A—C22A—C21A121.63 (14)C24B—C23B—H23B121.0
C23A—C22A—H22A119.2C22B—C23B—H23B121.0
C21A—C22A—H22A119.2F1B—C24B—C25B118.34 (17)
C24A—C23A—C22A118.22 (16)F1B—C24B—C23B118.70 (18)
C24A—C23A—H23A120.9C25B—C24B—C23B122.96 (16)
C22A—C23A—H23A120.9C24B—C25B—C26B118.30 (15)
F1A—C24A—C25A119.12 (14)C24B—C25B—H25B120.8
F1A—C24A—C23A118.55 (16)C26B—C25B—H25B120.8
C25A—C24A—C23A122.33 (15)C25B—C26B—C21B121.11 (16)
C24A—C25A—C26A118.66 (14)C25B—C26B—H26B119.4
C24A—C25A—H25A120.7C21B—C26B—H26B119.4
C26A—C25A—H25A120.7O2B—C27B—H27D109.5
C25A—C26A—C21A121.16 (15)O2B—C27B—H27E109.5
C25A—C26A—H26A119.4H27D—C27B—H27E109.5
C21A—C26A—H26A119.4O2B—C27B—H27F109.5
O2A—C27A—H27A109.5H27D—C27B—H27F109.5
O2A—C27A—H27B109.5H27E—C27B—H27F109.5
H27A—C27A—H27B109.5O3B—C28B—H28D109.5
O2A—C27A—H27C109.5O3B—C28B—H28E109.5
H27A—C27A—H27C109.5H28D—C28B—H28E109.5
H27B—C27A—H27C109.5O3B—C28B—H28F109.5
O3A—C28A—H28A109.5H28D—C28B—H28F109.5
O3A—C28A—H28B109.5H28E—C28B—H28F109.5
H28A—C28A—H28B109.5N1B—C29B—H29D109.5
O3A—C28A—H28C109.5N1B—C29B—H29E109.5
H28A—C28A—H28C109.5H29D—C29B—H29E109.5
H28B—C28A—H28C109.5N1B—C29B—H29F109.5
N1A—C29A—H29A109.5H29D—C29B—H29F109.5
N1A—C29A—H29B109.5H29E—C29B—H29F109.5
H29A—C29A—H29B109.5C30—O6—H1O6111.3 (18)
N1A—C29A—H29C109.5O6—C30—H30A109.5
H29A—C29A—H29C109.5O6—C30—H30B109.5
H29B—C29A—H29C109.5H30A—C30—H30B109.5
C4B—O2B—C27B115.48 (12)O6—C30—H30C109.5
C5B—O3B—C28B117.48 (11)H30A—C30—H30C109.5
C12B—N1B—C29B116.36 (12)H30B—C30—H30C109.5
C12B—N1B—C11B108.74 (11)
O1A—C1A—C2A—C7A172.47 (15)O1B—C1B—C2B—C7B171.09 (14)
C9A—C1A—C2A—C7A10.63 (16)C9B—C1B—C2B—C7B10.90 (15)
O1A—C1A—C2A—C3A8.6 (3)O1B—C1B—C2B—C3B9.2 (2)
C9A—C1A—C2A—C3A168.33 (14)C9B—C1B—C2B—C3B168.79 (14)
C7A—C2A—C3A—C4A0.3 (2)C7B—C2B—C3B—C4B1.0 (2)
C1A—C2A—C3A—C4A179.15 (14)C1B—C2B—C3B—C4B179.30 (14)
C27A—O2A—C4A—C3A3.5 (2)C27B—O2B—C4B—C3B11.1 (2)
C27A—O2A—C4A—C5A177.05 (13)C27B—O2B—C4B—C5B169.22 (13)
C2A—C3A—C4A—O2A178.90 (13)C2B—C3B—C4B—O2B176.79 (13)
C2A—C3A—C4A—C5A1.7 (2)C2B—C3B—C4B—C5B3.6 (2)
C28A—O3A—C5A—C6A16.5 (2)C28B—O3B—C5B—C6B10.0 (2)
C28A—O3A—C5A—C4A163.83 (13)C28B—O3B—C5B—C4B171.30 (13)
O2A—C4A—C5A—O3A1.07 (19)O2B—C4B—C5B—O3B3.72 (18)
C3A—C4A—C5A—O3A178.39 (13)C3B—C4B—C5B—O3B175.95 (13)
O2A—C4A—C5A—C6A178.61 (13)O2B—C4B—C5B—C6B175.04 (13)
C3A—C4A—C5A—C6A1.9 (2)C3B—C4B—C5B—C6B5.3 (2)
O3A—C5A—C6A—C7A179.75 (14)O3B—C5B—C6B—C7B179.17 (13)
C4A—C5A—C6A—C7A0.1 (2)C4B—C5B—C6B—C7B2.2 (2)
C3A—C2A—C7A—C6A2.1 (2)C3B—C2B—C7B—C6B4.1 (2)
C1A—C2A—C7A—C6A178.83 (13)C1B—C2B—C7B—C6B176.18 (13)
C3A—C2A—C7A—C8A178.17 (13)C3B—C2B—C7B—C8B176.41 (13)
C1A—C2A—C7A—C8A0.85 (17)C1B—C2B—C7B—C8B3.30 (16)
C5A—C6A—C7A—C2A1.9 (2)C5B—C6B—C7B—C2B2.4 (2)
C5A—C6A—C7A—C8A178.49 (14)C5B—C6B—C7B—C8B178.24 (14)
C2A—C7A—C8A—C9A9.12 (17)C2B—C7B—C8B—C9B5.56 (15)
C6A—C7A—C8A—C9A171.23 (15)C6B—C7B—C8B—C9B175.01 (14)
O1A—C1A—C9A—C8A167.21 (15)O1B—C1B—C9B—C8B168.11 (13)
C2A—C1A—C9A—C8A15.74 (15)C2B—C1B—C9B—C8B13.78 (14)
O1A—C1A—C9A—C10A37.81 (19)O1B—C1B—C9B—C10B40.27 (19)
C2A—C1A—C9A—C10A145.14 (12)C2B—C1B—C9B—C10B141.62 (12)
O1A—C1A—C9A—C12A73.47 (19)O1B—C1B—C9B—C12B70.62 (16)
C2A—C1A—C9A—C12A103.58 (13)C2B—C1B—C9B—C12B107.49 (12)
C7A—C8A—C9A—C1A14.71 (15)C7B—C8B—C9B—C1B11.48 (14)
C7A—C8A—C9A—C10A143.22 (13)C7B—C8B—C9B—C10B137.88 (12)
C7A—C8A—C9A—C12A104.13 (13)C7B—C8B—C9B—C12B108.38 (12)
C1A—C9A—C10A—C21A77.09 (15)C1B—C9B—C10B—C21B78.01 (15)
C8A—C9A—C10A—C21A46.31 (18)C8B—C9B—C10B—C21B43.66 (17)
C12A—C9A—C10A—C21A165.37 (12)C12B—C9B—C10B—C21B164.63 (11)
C1A—C9A—C10A—C11A153.05 (11)C1B—C9B—C10B—C11B151.70 (13)
C8A—C9A—C10A—C11A83.55 (14)C8B—C9B—C10B—C11B86.63 (15)
C12A—C9A—C10A—C11A35.51 (13)C12B—C9B—C10B—C11B34.33 (13)
C12A—N1A—C11A—C10A17.98 (15)C12B—N1B—C11B—C10B15.16 (17)
C29A—N1A—C11A—C10A150.38 (13)C29B—N1B—C11B—C10B147.94 (13)
C21A—C10A—C11A—N1A141.21 (13)C21B—C10B—C11B—N1B141.35 (13)
C9A—C10A—C11A—N1A12.82 (14)C9B—C10B—C11B—N1B13.70 (16)
C29A—N1A—C12A—C20A67.19 (18)C29B—N1B—C12B—C20B70.02 (17)
C11A—N1A—C12A—C20A161.56 (12)C11B—N1B—C12B—C20B157.75 (13)
C29A—N1A—C12A—C13A52.2 (2)C29B—N1B—C12B—C13B48.74 (17)
C11A—N1A—C12A—C13A79.06 (15)C11B—N1B—C12B—C13B83.49 (16)
C29A—N1A—C12A—C9A171.83 (14)C29B—N1B—C12B—C9B169.60 (12)
C11A—N1A—C12A—C9A40.58 (14)C11B—N1B—C12B—C9B37.37 (15)
C1A—C9A—C12A—N1A167.34 (12)C1B—C9B—C12B—N1B163.49 (10)
C8A—C9A—C12A—N1A77.04 (14)C8B—C9B—C12B—N1B80.01 (12)
C10A—C9A—C12A—N1A46.16 (13)C10B—C9B—C12B—N1B43.56 (12)
C1A—C9A—C12A—C20A70.19 (15)C1B—C9B—C12B—C20B73.41 (13)
C8A—C9A—C12A—C20A45.42 (14)C8B—C9B—C12B—C20B43.09 (14)
C10A—C9A—C12A—C20A168.62 (11)C10B—C9B—C12B—C20B166.66 (10)
C1A—C9A—C12A—C13A42.84 (16)C1B—C9B—C12B—C13B38.82 (14)
C8A—C9A—C12A—C13A158.46 (11)C8B—C9B—C12B—C13B155.32 (10)
C10A—C9A—C12A—C13A78.34 (13)C10B—C9B—C12B—C13B81.11 (12)
N1A—C12A—C13A—O4A32.5 (2)N1B—C12B—C13B—O4B31.6 (2)
C20A—C12A—C13A—O4A158.50 (15)C20B—C12B—C13B—O4B157.37 (16)
C9A—C12A—C13A—O4A81.81 (18)C9B—C12B—C13B—O4B84.55 (18)
N1A—C12A—C13A—C14A143.58 (13)N1B—C12B—C13B—C14B145.98 (13)
C20A—C12A—C13A—C14A17.63 (14)C20B—C12B—C13B—C14B20.21 (15)
C9A—C12A—C13A—C14A102.07 (14)C9B—C12B—C13B—C14B97.87 (13)
O4A—C13A—C14A—C19A165.60 (15)O4B—C13B—C14B—C19B165.96 (17)
C12A—C13A—C14A—C19A10.48 (16)C12B—C13B—C14B—C19B11.55 (18)
O4A—C13A—C14A—C15A12.3 (3)O4B—C13B—C14B—C15B16.3 (3)
C12A—C13A—C14A—C15A171.57 (15)C12B—C13B—C14B—C15B166.19 (17)
C19A—C14A—C15A—C16A0.5 (2)C19B—C14B—C15B—C16B1.6 (3)
C13A—C14A—C15A—C16A177.23 (15)C13B—C14B—C15B—C16B175.89 (17)
C14A—C15A—C16A—C17A0.7 (2)C14B—C15B—C16B—C17B1.1 (3)
C15A—C16A—C17A—C18A0.2 (3)C15B—C16B—C17B—C18B0.8 (3)
C16A—C17A—C18A—C19A0.6 (2)C16B—C17B—C18B—C19B2.2 (3)
C17A—C18A—C19A—C14A0.8 (2)C15B—C14B—C19B—C18B0.2 (3)
C17A—C18A—C19A—C20A174.99 (15)C13B—C14B—C19B—C18B177.76 (15)
C15A—C14A—C19A—C18A0.2 (2)C15B—C14B—C19B—C20B179.10 (15)
C13A—C14A—C19A—C18A178.36 (14)C13B—C14B—C19B—C20B2.96 (19)
C15A—C14A—C19A—C20A176.23 (13)C17B—C18B—C19B—C14B1.8 (3)
C13A—C14A—C19A—C20A1.90 (17)C17B—C18B—C19B—C20B179.11 (17)
C18A—C19A—C20A—O5A12.4 (3)C14B—C19B—C20B—O5B162.86 (17)
C14A—C19A—C20A—O5A163.70 (15)C18B—C19B—C20B—O5B16.4 (3)
C18A—C19A—C20A—C12A170.24 (15)C14B—C19B—C20B—C12B16.38 (18)
C14A—C19A—C20A—C12A13.61 (16)C18B—C19B—C20B—C12B164.40 (16)
N1A—C12A—C20A—O5A31.0 (2)N1B—C12B—C20B—O5B30.7 (2)
C13A—C12A—C20A—O5A158.67 (15)C13B—C12B—C20B—O5B157.38 (17)
C9A—C12A—C20A—O5A83.19 (18)C9B—C12B—C20B—O5B84.71 (19)
N1A—C12A—C20A—C19A146.33 (12)N1B—C12B—C20B—C19B148.57 (13)
C13A—C12A—C20A—C19A18.67 (14)C13B—C12B—C20B—C19B21.86 (16)
C9A—C12A—C20A—C19A99.47 (13)C9B—C12B—C20B—C19B96.05 (14)
C11A—C10A—C21A—C22A152.37 (15)C11B—C10B—C21B—C22B149.87 (13)
C9A—C10A—C21A—C22A84.84 (17)C9B—C10B—C21B—C22B87.23 (15)
C11A—C10A—C21A—C26A27.8 (2)C11B—C10B—C21B—C26B33.80 (19)
C9A—C10A—C21A—C26A94.95 (17)C9B—C10B—C21B—C26B89.10 (16)
C26A—C21A—C22A—C23A1.1 (2)C26B—C21B—C22B—C23B1.6 (2)
C10A—C21A—C22A—C23A179.15 (14)C10B—C21B—C22B—C23B178.14 (13)
C21A—C22A—C23A—C24A0.5 (2)C21B—C22B—C23B—C24B0.9 (2)
C22A—C23A—C24A—F1A177.43 (15)C22B—C23B—C24B—F1B179.86 (14)
C22A—C23A—C24A—C25A1.9 (3)C22B—C23B—C24B—C25B0.5 (2)
F1A—C24A—C25A—C26A177.74 (15)F1B—C24B—C25B—C26B179.24 (14)
C23A—C24A—C25A—C26A1.6 (3)C23B—C24B—C25B—C26B1.1 (2)
C24A—C25A—C26A—C21A0.1 (2)C24B—C25B—C26B—C21B0.3 (2)
C22A—C21A—C26A—C25A1.4 (2)C22B—C21B—C26B—C25B1.0 (2)
C10A—C21A—C26A—C25A178.84 (15)C10B—C21B—C26B—C25B177.34 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H1O6···O4A0.97 (3)1.99 (3)2.9346 (18)164 (3)
C8A—H8AA···O5A0.992.433.088 (2)124
C8B—H8BA···O5B0.992.383.0960 (19)128
C26A—H26A···O5Ai0.952.543.2430 (18)131
C27A—H27A···N1Bii0.982.423.337 (2)155
C28A—H28A···O2Biii0.982.503.3478 (19)145
C28B—H28F···O6iv0.982.463.360 (2)153
C30—H30B···F1Av0.982.533.307 (2)136
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y+2, z+2; (iv) x+1, y, z; (v) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H1O6···O4A0.97 (3)1.99 (3)2.9346 (18)164 (3)
C8A—H8AA···O5A0.992.433.088 (2)124
C8B—H8BA···O5B0.992.383.0960 (19)128
C26A—H26A···O5Ai0.952.543.2430 (18)131
C27A—H27A···N1Bii0.982.423.337 (2)155
C28A—H28A···O2Biii0.982.503.3478 (19)145
C28B—H28F···O6iv0.982.463.360 (2)153
C30—H30B···F1Av0.982.533.307 (2)136
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+1/2, z+3/2; (iii) x+2, y+2, z+2; (iv) x+1, y, z; (v) x+1, y+1, z+2.
Acknowledgements top

The authors wish to express their gratitude and appreciation to the Pharmacogenetics and Novel Therapeutics Research Cluster, Institute for Research in Molecular Medicine, Universiti Sains Malaysia (USM), Penang, for support of this work. This work was funded through Research Grant No. RUC (1001/PSK/8620012) and HiCoE Research Grant No (311.CIPPM.4401005). IAR also thanks USM for the Short Term Grant, No. 304/PFIZIK/6312078.

references
References top

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