supplementary materials


xu5738 scheme

Acta Cryst. (2013). E69, o1626-o1627    [ doi:10.1107/S1600536813027281 ]

2,2'-Bis{8-[(benzyl­amino)­methyl­idene]-1,6-dihy­droxy-5-isopropyl-3-methyl­naphthalen-7(8H)-one}

S. M. Hakberdiev, S. A. Talipov, D. N. Dalimov and B. T. Ibragimov

Abstract top

The asymmetric unit of the title compound, C44H44N2O6, contains two independent mol­ecules with similar conformations. The di­hydro­naphthalene ring systems are approximately planar [maximum deviations = 0.036 (2), 0.128 (2), 0.0.24 (2) and 0.075 (2) Å]. The dihedral angle between two di­hydro­naphthalene ring systems is 83.37 (4)° in one mol­ecule and 88.99 (4)° in the other. The carbonyl O atom is linked with the adjacent hy­droxy and imino groups via intra­molecular O-H...O and N-H...O hydrogen bonds. In the crystal, mol­ecules are linked through O-H...O hydrogen bonds into layers parallel to (001), and adjacent layers are further stacked by [pi]-[pi] inter­actions between di­hydro­naphthalene and phenyl rings into a three-dimensional supra­molecular architecture. In the crystal, one of the isopropyl groups is disordered over two positions with an occupancy ratio of 0.684 (8):0.316 (8).

Comment top

Bis-benzylaminogossypol (2,2'-bis(1,6-dihydroxy,-5-isopropyl 8-methine-aminobenzyl-3-methylnaphthalene-7-one), C44H44O6N2) is Shiff base derivative of gossypol, a phenolic pigment extracted from cotton seeds (Kenar, 2006). Gossypol demonstrates wide range of biological activities (Polsky et al., 1989: Radloff et al., 1985) and versatile host properties (Ibragimov & Talipov, 1999; 2004). Herein, we describe the crystal structure of bis-benzylaminogossypol. The asymmetric unit of the crystal structure consists of two independent molecules A and B which are linked by a pair of strong O5A—H···O3B and O5B—H···O3A hydrogen bonds and the molecules form a dimer. Molecules of the title compound is racemic and in the enamine tautomer form. The naphthyl moieties of both molecules are planar and nearly perpendicular, the dihedral angles between their least-squares planes are 83.36 (5)° and 89.04 (5)° in the molecules A and B (Fig.1), respectively. The tilt angle between the benzyl rings and corresponding naphtyl moiety are different: (C1A—C10A)/(C31A—C37A) - 9.14 (16)°; (C11A—C20A)/(C38A—C44A) -52.66 (11)°; (C1B—C10B)/(C31B—C37B) -4.41 (14)°; (C11B—C20B)/(C38B—C44B) -65.51 (11)°. Isopropyl group (to C15A) are disordered. In the crystal structure (Fig.2), the dimers of title compound are linked through O1A—H···O7B, O1B—H···O7A, O8A—H···O1B and O8B—H···O1A hydrogen bonds into layers parallel to (0 0 1) (Table 1).

Related literature top

For details of extraction and synthesis of gossypol and its derivatives, see: Kenar (2006). For synthesis and biological activities, see: Polsky et al. (1989); Radloff et al. (1985). For formation of crystalline forms of inclusion compounds, see: Ibragimov & Talipov (1999, 2004).

Experimental top

Gossypol was obtained from the Experimental Plant of the Institute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan where it was produced from by-products of the cottonseed oil industry. To prepare the Schiff base compound, gossypol was mixed with benzylamine in a 1:3 molar ratio in the acetone. This reaction solution was allowed to stand in the dark for 3 days, during which crystalline precipitate formed within solution. The precipitate was recovered by filtration and air-dried. Suitable crystals were selected from the precipitate and were used for diffraction without additional recrystallization.

Refinement top

The H atoms attached to oxygen atoms were found from the difference Fourier maps and were refined isotropically, other H atoms were placed in geometrically idealized positions (N—H = 0.86, C—H = 0.93–0.96 Å, and treated as riding on their parent atoms with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(C). One of isopropyl group is disordered over two positions, occupancies were refined to 0.684 (8):0.316 (8).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram for title compound.
2,2'-Bis{8-[(benzylamino)methylidene]-1,6-dihydroxy-5-isopropyl-8-[(benzylamino)methylidene]-3-methylnaphthalen-7(8H)-one} top
Crystal data top
C44H44N2O6F(000) = 2960
Mr = 696.81Dx = 1.271 Mg m3
Dm = 1.271 Mg m3
Dm measured by not measured
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.8118 (8) ÅCell parameters from 3347 reflections
b = 29.014 (2) Åθ = 3.5–36.0°
c = 25.5854 (17) ŵ = 0.68 mm1
β = 90.196 (6)°T = 293 K
V = 7283.6 (9) Å3Prism, brown
Z = 80.6 × 0.3 × 0.2 mm
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
15043 independent reflections
Radiation source: fine-focus sealed tube7763 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 10.2576 pixels mm-1θmax = 76.8°, θmin = 3.5°
ω scansh = 1112
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 3336
Tmin = 0.66, Tmax = 0.88l = 3131
54670 measured reflections
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)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.106P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.002
15043 reflectionsΔρmax = 0.22 e Å3
1001 parametersΔρmin = 0.26 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00014 (3)
Crystal data top
C44H44N2O6V = 7283.6 (9) Å3
Mr = 696.81Z = 8
Monoclinic, P21/cCu Kα radiation
a = 9.8118 (8) ŵ = 0.68 mm1
b = 29.014 (2) ÅT = 293 K
c = 25.5854 (17) Å0.6 × 0.3 × 0.2 mm
β = 90.196 (6)°
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
15043 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
7763 reflections with I > 2σ(I)
Tmin = 0.66, Tmax = 0.88Rint = 0.049
54670 measured reflectionsθmax = 76.8°
Refinement top
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.191Δρmax = 0.22 e Å3
S = 0.94Δρmin = 0.26 e Å3
15043 reflectionsAbsolute structure: ?
1001 parametersAbsolute structure parameter: ?
3 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)
O1A0.3398 (2)0.50674 (7)0.30051 (8)0.0599 (5)
O3A0.51864 (19)0.35070 (6)0.23365 (8)0.0662 (5)
O4A0.3897 (3)0.28774 (7)0.28570 (10)0.0758 (7)
O5A0.0079 (2)0.54677 (7)0.30415 (8)0.0600 (5)
O7A0.1016 (2)0.71837 (6)0.31337 (8)0.0670 (5)
O8A0.0477 (2)0.75200 (6)0.38755 (10)0.0760 (6)
N1A0.5755 (2)0.43231 (8)0.21212 (9)0.0612 (6)
H1AN0.58110.40320.20600.073*
N2A0.2222 (2)0.65010 (8)0.26806 (9)0.0620 (6)
H2AN0.21130.67950.26930.074*
C1A0.2683 (2)0.47309 (8)0.32578 (9)0.0449 (5)
C2A0.1730 (2)0.48497 (8)0.36297 (9)0.0442 (5)
C3A0.1000 (2)0.44951 (8)0.38860 (9)0.0463 (6)
C4A0.1287 (2)0.40481 (8)0.37605 (10)0.0484 (6)
H40.08010.38170.39300.058*
C5A0.2540 (3)0.34321 (8)0.32885 (10)0.0538 (6)
C6A0.3536 (3)0.33248 (8)0.29462 (11)0.0549 (7)
C7A0.4285 (3)0.36623 (9)0.26604 (10)0.0522 (6)
C8A0.4036 (2)0.41362 (8)0.27448 (9)0.0469 (6)
C9A0.3011 (2)0.42680 (8)0.31242 (9)0.0422 (5)
C10A0.2273 (2)0.39184 (8)0.33906 (9)0.0452 (6)
C11A0.0709 (2)0.56317 (8)0.34810 (9)0.0449 (5)
C12A0.1535 (2)0.53450 (8)0.37748 (9)0.0456 (6)
C13A0.2189 (3)0.55251 (8)0.42227 (10)0.0507 (6)
C14A0.2018 (3)0.59822 (8)0.43407 (10)0.0527 (6)
H14A0.24560.61000.46340.063*
C15A0.1140 (3)0.67728 (8)0.41650 (11)0.0537 (6)
C16A0.0481 (3)0.70493 (8)0.38213 (11)0.0550 (7)
C17A0.0340 (3)0.68878 (8)0.33948 (10)0.0524 (6)
C18A0.0404 (3)0.64017 (8)0.33049 (9)0.0472 (6)
C19A0.0487 (2)0.61000 (8)0.36051 (9)0.0452 (5)
C20A0.1213 (3)0.62822 (8)0.40407 (10)0.0478 (6)
C21A0.0057 (3)0.46067 (9)0.42926 (11)0.0617 (7)
H21A0.07880.47760.41340.093*
H21B0.04070.43260.44390.093*
H21C0.03470.47890.45640.093*
C22A0.4844 (3)0.44502 (9)0.24534 (10)0.0574 (7)
H22A0.47080.47640.25050.069*
C23A0.1769 (4)0.30519 (9)0.35660 (13)0.0762 (9)
H23A0.09820.31970.37360.091*
C24A0.1200 (4)0.26728 (11)0.32034 (16)0.0973 (12)
H24A0.19340.24820.30810.146*
H24B0.05570.24870.33930.146*
H24C0.07550.28130.29100.146*
C25A0.2630 (6)0.28451 (14)0.39965 (15)0.1304 (18)
H25A0.28120.30750.42560.196*
H25B0.21500.25920.41540.196*
H25C0.34760.27370.38520.196*
C26A0.3089 (3)0.52265 (9)0.45625 (11)0.0675 (8)
H26A0.38930.51420.43710.101*
H26B0.33430.53950.48700.101*
H26C0.26000.49530.46620.101*
C27A0.1424 (3)0.62403 (9)0.29687 (10)0.0519 (6)
H27A0.15460.59230.29470.062*
C28A0.1746 (4)0.69730 (10)0.46614 (13)0.0785 (9)
H28A0.14500.72950.46470.094*0.684 (8)
H28C0.24810.67470.47010.094*0.316 (8)
C29A0.1023 (9)0.6797 (3)0.5133 (3)0.076 (2)0.684 (8)
H29A0.12950.64840.51980.114*0.684 (8)
H29B0.12520.69850.54290.114*0.684 (8)
H29C0.00570.68080.50760.114*0.684 (8)
C30A0.3198 (5)0.7014 (2)0.4704 (2)0.0801 (19)0.684 (8)
H30A0.36130.67210.46350.120*0.684 (8)
H30B0.35230.72360.44550.120*0.684 (8)
H30C0.34290.71130.50510.120*0.684 (8)
C29C0.2682 (13)0.7406 (4)0.4553 (5)0.096 (5)0.316 (8)
H29G0.30450.73880.42040.143*0.316 (8)
H29H0.21520.76830.45880.143*0.316 (8)
H29I0.34170.74110.47990.143*0.316 (8)
C30C0.114 (3)0.6915 (10)0.5192 (6)0.181 (15)0.316 (8)
H30G0.06400.66320.52060.271*0.316 (8)
H30H0.18590.69080.54470.271*0.316 (8)
H30I0.05440.71690.52650.271*0.316 (8)
C31A0.6679 (4)0.46109 (12)0.18448 (16)0.0955 (12)
H31A0.61650.48550.16770.115*
H31B0.72870.47550.20950.115*
C32A0.7541 (3)0.43661 (13)0.14295 (14)0.0817 (9)
C33A0.7725 (4)0.38898 (14)0.14119 (16)0.0953 (12)
H33A0.72680.36980.16450.114*
C34A0.8578 (5)0.37130 (18)0.10505 (19)0.1115 (14)
H34A0.87190.33960.10540.134*
C35A0.9227 (5)0.3955 (2)0.0693 (2)0.1365 (19)
H35A0.97670.38140.04400.164*
C36A0.9066 (7)0.4430 (2)0.0712 (2)0.163 (2)
H36A0.95410.46200.04820.196*
C37A0.8190 (5)0.46168 (19)0.10773 (19)0.1387 (19)
H37A0.80510.49340.10760.166*
C38A0.3275 (3)0.63183 (12)0.23430 (12)0.0745 (9)
H38A0.35790.60240.24810.089*
H38B0.40480.65270.23480.089*
C39A0.2821 (3)0.62517 (11)0.17855 (13)0.0731 (8)
C40A0.1828 (5)0.59550 (17)0.16518 (17)0.1199 (16)
H40A0.13860.57840.19080.144*
C41A0.1461 (6)0.5904 (2)0.1129 (2)0.149 (2)
H41A0.07640.57020.10370.179*
C42A0.2109 (8)0.6145 (2)0.0753 (2)0.150 (3)
H42A0.18720.61080.04040.180*
C43A0.3105 (7)0.6441 (2)0.0893 (2)0.156 (2)
H43A0.35540.66120.06390.187*
C44A0.3451 (5)0.64900 (15)0.13937 (16)0.1105 (14)
H44A0.41470.66940.14800.133*
H1A0.319 (3)0.5272 (9)0.3076 (10)0.043 (9)*
H4AB0.437 (3)0.2912 (11)0.2635 (13)0.075 (13)*
H5A0.019 (3)0.5211 (10)0.2998 (11)0.070 (10)*
H8A0.009 (6)0.7604 (18)0.361 (2)0.19 (2)*
O1B0.1752 (2)0.31302 (6)0.17875 (8)0.0614 (5)
O3B0.0174 (2)0.47414 (7)0.23736 (8)0.0749 (6)
O4B0.1476 (3)0.53280 (7)0.18104 (13)0.0950 (8)
O5B0.5256 (2)0.27491 (6)0.17625 (8)0.0617 (5)
O7B0.6126 (2)0.10094 (6)0.19258 (8)0.0639 (5)
O8B0.4496 (2)0.06113 (6)0.12801 (10)0.0781 (7)
N1B0.0548 (2)0.39295 (8)0.26071 (9)0.0612 (6)
H1BN0.05980.42200.26690.073*
N2B0.7309 (2)0.17165 (8)0.23157 (9)0.0591 (6)
H2BN0.72220.14220.23130.071*
C1B0.2491 (3)0.34500 (8)0.15120 (10)0.0482 (6)
C2B0.3468 (3)0.33002 (8)0.11598 (9)0.0476 (6)
C3B0.4201 (3)0.36252 (9)0.08731 (10)0.0530 (6)
C4B0.3928 (3)0.40850 (9)0.09530 (11)0.0610 (7)
H4B0.44170.43000.07590.073*
C5B0.2728 (3)0.47405 (9)0.13804 (13)0.0672 (8)
C6B0.1792 (3)0.48738 (9)0.17298 (13)0.0680 (8)
C7B0.1010 (3)0.45603 (9)0.20466 (11)0.0582 (7)
C8B0.1189 (2)0.40818 (8)0.19770 (10)0.0483 (6)
C9B0.2192 (2)0.39209 (8)0.16036 (10)0.0468 (6)
C10B0.2958 (3)0.42474 (8)0.13102 (11)0.0540 (6)
C11B0.4478 (2)0.25358 (8)0.13916 (9)0.0464 (6)
C12B0.3616 (3)0.27949 (8)0.10783 (10)0.0479 (6)
C13B0.2832 (3)0.25708 (9)0.06921 (10)0.0516 (6)
C14B0.2905 (3)0.20996 (8)0.06589 (10)0.0531 (6)
H14B0.23850.19520.04060.064*
C15B0.3681 (3)0.13275 (8)0.09532 (10)0.0499 (6)
C16B0.4483 (3)0.10820 (8)0.12741 (11)0.0540 (6)
C17B0.5413 (3)0.12858 (8)0.16441 (10)0.0496 (6)
C18B0.5507 (2)0.17727 (8)0.16775 (9)0.0461 (6)
C19B0.4589 (2)0.20484 (8)0.13539 (9)0.0452 (5)
C20B0.3724 (2)0.18272 (8)0.09873 (9)0.0463 (6)
C21B0.5251 (3)0.34706 (11)0.04815 (12)0.0731 (9)
H21D0.48240.32830.02200.110*
H21F0.56560.37350.03180.110*
H21E0.59430.32950.06560.110*
C22B0.0336 (3)0.37892 (9)0.22677 (11)0.0568 (7)
H22B0.04130.34730.22120.068*
C23B0.3500 (4)0.50935 (11)0.10536 (19)0.1092 (14)
H23B0.43020.49310.09180.131*
C24B0.2709 (7)0.52298 (19)0.0589 (2)0.181 (3)
H24D0.18360.53460.06970.272*
H24E0.31920.54660.04010.272*
H24F0.25840.49670.03660.272*
C25B0.4062 (5)0.55037 (14)0.1370 (3)0.165 (2)
H25D0.44310.53940.16940.247*
H25E0.47660.56540.11720.247*
H25F0.33390.57180.14400.247*
C26B0.1927 (3)0.28431 (10)0.03317 (11)0.0665 (8)
H26F0.24790.30350.01100.100*
H26D0.14020.26350.01210.100*
H26E0.13240.30330.05350.100*
C27B0.6516 (3)0.19577 (9)0.20076 (10)0.0515 (6)
H27B0.66280.22760.20070.062*
C28B0.2757 (3)0.11051 (9)0.05479 (11)0.0603 (7)
H28B0.19750.13120.05080.072*
C29B0.3490 (4)0.11025 (11)0.00226 (12)0.0783 (9)
H29E0.42270.08850.00330.117*
H29D0.28610.10160.02470.117*
H29F0.38420.14050.00490.117*
C30B0.2174 (3)0.06336 (10)0.06733 (13)0.0739 (9)
H30D0.19350.06200.10370.111*
H30E0.13770.05810.04660.111*
H30F0.28430.04010.05970.111*
C31B0.1449 (3)0.36288 (11)0.28869 (14)0.0822 (10)
H31C0.20160.34670.26370.099*
H31D0.09100.34010.30700.099*
C32B0.2354 (3)0.38680 (11)0.32731 (12)0.0679 (8)
C33B0.3082 (4)0.36054 (14)0.36087 (14)0.0946 (11)
H33B0.29740.32870.36010.114*
C34B0.3972 (5)0.37956 (18)0.39591 (17)0.1196 (15)
H34B0.44700.36080.41840.144*
C35B0.4129 (4)0.42655 (17)0.39777 (15)0.0977 (13)
H35B0.47260.43990.42170.117*
C36B0.3420 (4)0.45267 (14)0.36510 (16)0.0928 (11)
H36B0.35280.48450.36630.111*
C37B0.2527 (3)0.43390 (12)0.32942 (13)0.0789 (9)
H37B0.20420.45290.30680.095*
C38B0.8325 (3)0.19135 (11)0.26616 (11)0.0678 (8)
H38C0.91600.17360.26310.081*
H38D0.85220.22260.25490.081*
C39B0.7893 (3)0.19230 (11)0.32213 (13)0.0679 (8)
C40B0.8537 (6)0.16527 (16)0.35764 (17)0.1373 (19)
H40B0.92300.14560.34670.165*
C41B0.8171 (10)0.1668 (2)0.4103 (2)0.195 (3)
H41B0.86230.14840.43440.234*
C42B0.7170 (8)0.1947 (3)0.4261 (3)0.167 (3)
H42B0.69090.19510.46100.200*
C43B0.6554 (6)0.2217 (3)0.3926 (3)0.160 (3)
H43B0.58740.24160.40420.192*
C44B0.6911 (4)0.22078 (17)0.33914 (18)0.1212 (17)
H44B0.64650.24000.31570.145*
H1B0.209 (3)0.2892 (11)0.1740 (12)0.081 (11)*
H4BC0.090 (5)0.5312 (16)0.2050 (18)0.14 (2)*
H5B0.509 (3)0.3021 (10)0.1796 (11)0.063 (9)*
H8B0.512 (5)0.0569 (16)0.1514 (19)0.17 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0747 (13)0.0302 (11)0.0748 (13)0.0014 (9)0.0184 (10)0.0040 (9)
O3A0.0655 (12)0.0554 (12)0.0777 (13)0.0064 (9)0.0126 (10)0.0225 (10)
O4A0.0997 (18)0.0342 (11)0.0932 (17)0.0114 (10)0.0250 (15)0.0085 (10)
O5A0.0788 (13)0.0384 (11)0.0629 (12)0.0152 (9)0.0150 (10)0.0141 (9)
O7A0.0913 (14)0.0373 (10)0.0722 (12)0.0152 (9)0.0054 (11)0.0070 (9)
O8A0.0984 (17)0.0290 (10)0.1005 (17)0.0028 (10)0.0002 (14)0.0069 (10)
N1A0.0600 (14)0.0557 (14)0.0679 (15)0.0071 (11)0.0175 (12)0.0110 (11)
N2A0.0710 (15)0.0531 (14)0.0619 (14)0.0147 (11)0.0034 (12)0.0032 (11)
C1A0.0496 (14)0.0322 (12)0.0529 (14)0.0008 (10)0.0018 (12)0.0004 (10)
C2A0.0508 (14)0.0316 (12)0.0502 (13)0.0063 (10)0.0029 (11)0.0014 (10)
C3A0.0511 (14)0.0375 (13)0.0504 (14)0.0025 (10)0.0010 (11)0.0007 (10)
C4A0.0534 (15)0.0339 (13)0.0577 (15)0.0007 (10)0.0036 (12)0.0030 (10)
C5A0.0647 (16)0.0337 (13)0.0630 (16)0.0017 (11)0.0029 (14)0.0017 (11)
C6A0.0656 (17)0.0340 (13)0.0650 (17)0.0052 (11)0.0005 (14)0.0085 (11)
C7A0.0553 (15)0.0452 (15)0.0559 (15)0.0039 (11)0.0005 (13)0.0116 (12)
C8A0.0490 (14)0.0406 (13)0.0510 (14)0.0014 (10)0.0031 (11)0.0057 (10)
C9A0.0436 (13)0.0348 (12)0.0483 (13)0.0016 (9)0.0025 (11)0.0056 (10)
C10A0.0498 (14)0.0343 (12)0.0516 (14)0.0036 (10)0.0013 (11)0.0016 (10)
C11A0.0512 (14)0.0355 (13)0.0480 (13)0.0034 (10)0.0029 (11)0.0025 (10)
C12A0.0526 (14)0.0328 (12)0.0513 (14)0.0051 (10)0.0054 (12)0.0021 (10)
C13A0.0610 (16)0.0375 (14)0.0536 (14)0.0044 (11)0.0007 (12)0.0008 (11)
C14A0.0672 (17)0.0371 (13)0.0540 (15)0.0012 (11)0.0036 (13)0.0052 (11)
C15A0.0597 (16)0.0374 (14)0.0641 (16)0.0016 (11)0.0076 (13)0.0078 (11)
C16A0.0663 (17)0.0295 (13)0.0690 (17)0.0013 (11)0.0144 (14)0.0037 (11)
C17A0.0663 (17)0.0336 (13)0.0573 (15)0.0062 (11)0.0098 (13)0.0025 (11)
C18A0.0565 (15)0.0374 (13)0.0476 (13)0.0053 (11)0.0088 (12)0.0005 (10)
C19A0.0514 (14)0.0349 (13)0.0493 (14)0.0026 (10)0.0093 (11)0.0014 (10)
C20A0.0551 (15)0.0337 (13)0.0545 (14)0.0004 (10)0.0063 (12)0.0023 (10)
C21A0.0690 (18)0.0488 (16)0.0674 (18)0.0068 (13)0.0127 (15)0.0020 (13)
C22A0.0607 (17)0.0467 (16)0.0649 (17)0.0000 (12)0.0036 (14)0.0068 (13)
C23A0.099 (2)0.0349 (15)0.094 (2)0.0027 (14)0.0294 (19)0.0025 (14)
C24A0.106 (3)0.048 (2)0.138 (3)0.0174 (18)0.002 (2)0.004 (2)
C25A0.234 (6)0.078 (3)0.079 (3)0.025 (3)0.007 (3)0.019 (2)
C26A0.087 (2)0.0476 (16)0.0678 (18)0.0081 (14)0.0175 (16)0.0005 (13)
C27A0.0596 (16)0.0432 (14)0.0528 (15)0.0100 (12)0.0082 (13)0.0021 (11)
C28A0.103 (3)0.0453 (17)0.088 (2)0.0086 (16)0.018 (2)0.0123 (15)
C29A0.090 (5)0.080 (4)0.059 (4)0.011 (3)0.009 (3)0.024 (3)
C30A0.069 (3)0.077 (4)0.094 (4)0.009 (3)0.011 (3)0.019 (3)
C29C0.088 (9)0.083 (10)0.116 (10)0.035 (7)0.001 (7)0.040 (8)
C30C0.16 (2)0.28 (4)0.103 (15)0.10 (2)0.037 (13)0.103 (17)
C31A0.096 (3)0.073 (2)0.118 (3)0.0041 (19)0.034 (2)0.001 (2)
C32A0.072 (2)0.093 (3)0.081 (2)0.0022 (19)0.0079 (18)0.002 (2)
C33A0.087 (3)0.099 (3)0.101 (3)0.024 (2)0.012 (2)0.017 (2)
C34A0.103 (3)0.122 (4)0.109 (3)0.021 (3)0.002 (3)0.021 (3)
C35A0.122 (4)0.180 (6)0.107 (4)0.017 (4)0.028 (3)0.019 (4)
C36A0.183 (6)0.161 (6)0.145 (5)0.000 (5)0.079 (4)0.014 (4)
C37A0.152 (4)0.135 (4)0.129 (4)0.005 (3)0.070 (4)0.012 (3)
C38A0.0644 (19)0.089 (2)0.070 (2)0.0120 (16)0.0059 (16)0.0070 (17)
C39A0.075 (2)0.074 (2)0.071 (2)0.0008 (16)0.0025 (17)0.0031 (16)
C40A0.122 (4)0.147 (4)0.090 (3)0.043 (3)0.009 (3)0.016 (3)
C41A0.148 (5)0.171 (6)0.128 (4)0.005 (4)0.054 (4)0.041 (4)
C42A0.211 (7)0.162 (6)0.075 (3)0.048 (5)0.025 (4)0.011 (4)
C43A0.212 (7)0.171 (6)0.086 (4)0.019 (5)0.009 (4)0.030 (4)
C44A0.141 (4)0.110 (3)0.081 (3)0.015 (3)0.001 (3)0.026 (2)
O1B0.0779 (13)0.0323 (10)0.0738 (13)0.0018 (9)0.0263 (10)0.0036 (9)
O3B0.0786 (14)0.0537 (12)0.0922 (15)0.0171 (10)0.0036 (12)0.0267 (11)
O4B0.112 (2)0.0351 (12)0.137 (2)0.0174 (12)0.0101 (19)0.0076 (13)
O5B0.0749 (13)0.0356 (11)0.0748 (13)0.0057 (9)0.0098 (10)0.0152 (9)
O7B0.0749 (13)0.0391 (10)0.0778 (13)0.0067 (9)0.0053 (11)0.0017 (9)
O8B0.0873 (16)0.0312 (10)0.1159 (19)0.0006 (9)0.0212 (14)0.0076 (10)
N1B0.0565 (13)0.0566 (14)0.0703 (15)0.0042 (11)0.0132 (12)0.0166 (11)
N2B0.0639 (14)0.0479 (13)0.0655 (14)0.0018 (10)0.0047 (12)0.0057 (11)
C1B0.0580 (15)0.0344 (13)0.0521 (14)0.0001 (11)0.0017 (12)0.0023 (10)
C2B0.0589 (15)0.0339 (13)0.0501 (14)0.0030 (10)0.0030 (12)0.0037 (10)
C3B0.0570 (15)0.0451 (15)0.0570 (15)0.0003 (11)0.0072 (13)0.0004 (11)
C4B0.0673 (18)0.0450 (16)0.0706 (18)0.0029 (13)0.0094 (15)0.0078 (13)
C5B0.0669 (18)0.0341 (14)0.101 (2)0.0012 (12)0.0011 (17)0.0011 (14)
C6B0.075 (2)0.0330 (14)0.096 (2)0.0094 (13)0.0088 (18)0.0084 (14)
C7B0.0585 (16)0.0462 (15)0.0699 (18)0.0091 (12)0.0072 (14)0.0109 (13)
C8B0.0484 (14)0.0404 (14)0.0562 (15)0.0051 (10)0.0031 (12)0.0104 (11)
C9B0.0506 (14)0.0341 (13)0.0556 (14)0.0020 (10)0.0046 (12)0.0048 (10)
C10B0.0564 (16)0.0340 (13)0.0717 (17)0.0005 (11)0.0006 (14)0.0019 (12)
C11B0.0530 (14)0.0364 (13)0.0496 (14)0.0032 (10)0.0082 (12)0.0097 (10)
C12B0.0557 (15)0.0368 (13)0.0511 (14)0.0019 (10)0.0127 (12)0.0040 (10)
C13B0.0617 (16)0.0439 (15)0.0493 (14)0.0033 (11)0.0053 (12)0.0038 (11)
C14B0.0624 (16)0.0440 (15)0.0528 (15)0.0003 (12)0.0027 (13)0.0100 (11)
C15B0.0522 (15)0.0368 (13)0.0606 (15)0.0018 (10)0.0070 (12)0.0111 (11)
C16B0.0566 (15)0.0326 (13)0.0727 (18)0.0005 (11)0.0036 (14)0.0083 (12)
C17B0.0507 (14)0.0396 (14)0.0585 (15)0.0024 (11)0.0072 (12)0.0033 (11)
C18B0.0499 (14)0.0353 (13)0.0530 (14)0.0010 (10)0.0094 (11)0.0070 (10)
C19B0.0510 (14)0.0365 (13)0.0480 (13)0.0009 (10)0.0093 (11)0.0042 (10)
C20B0.0494 (14)0.0403 (13)0.0492 (13)0.0004 (10)0.0092 (11)0.0082 (10)
C21B0.079 (2)0.066 (2)0.075 (2)0.0026 (16)0.0229 (17)0.0000 (16)
C22B0.0565 (16)0.0476 (16)0.0664 (17)0.0060 (12)0.0010 (14)0.0139 (13)
C23B0.130 (3)0.0405 (19)0.157 (4)0.0075 (19)0.042 (3)0.008 (2)
C24B0.225 (7)0.156 (5)0.164 (5)0.033 (5)0.007 (5)0.093 (4)
C25B0.133 (4)0.057 (3)0.304 (8)0.026 (3)0.022 (5)0.004 (4)
C26B0.083 (2)0.0548 (18)0.0620 (17)0.0074 (14)0.0072 (16)0.0031 (13)
C27B0.0553 (15)0.0392 (14)0.0598 (16)0.0000 (11)0.0042 (13)0.0066 (11)
C28B0.0679 (18)0.0410 (15)0.0719 (18)0.0004 (12)0.0026 (15)0.0086 (13)
C29B0.102 (2)0.065 (2)0.068 (2)0.0100 (17)0.0082 (18)0.0068 (15)
C30B0.077 (2)0.0592 (19)0.086 (2)0.0146 (15)0.0040 (17)0.0182 (16)
C31B0.078 (2)0.070 (2)0.098 (3)0.0057 (17)0.025 (2)0.0113 (18)
C32B0.0563 (17)0.078 (2)0.0694 (19)0.0081 (15)0.0024 (15)0.0118 (16)
C33B0.095 (3)0.100 (3)0.089 (3)0.010 (2)0.030 (2)0.001 (2)
C34B0.133 (4)0.126 (4)0.099 (3)0.017 (3)0.044 (3)0.006 (3)
C35B0.080 (3)0.135 (4)0.078 (2)0.024 (2)0.015 (2)0.022 (2)
C36B0.083 (2)0.096 (3)0.099 (3)0.018 (2)0.003 (2)0.026 (2)
C37B0.066 (2)0.081 (2)0.089 (2)0.0139 (17)0.0082 (18)0.0185 (18)
C38B0.0587 (17)0.075 (2)0.0698 (19)0.0017 (14)0.0018 (15)0.0074 (16)
C39B0.0688 (19)0.0627 (19)0.072 (2)0.0074 (15)0.0046 (16)0.0122 (15)
C40B0.214 (6)0.112 (4)0.086 (3)0.042 (4)0.014 (3)0.015 (3)
C41B0.358 (12)0.143 (6)0.084 (4)0.003 (6)0.031 (5)0.021 (3)
C42B0.212 (8)0.175 (7)0.112 (5)0.069 (6)0.072 (5)0.037 (5)
C43B0.112 (4)0.237 (9)0.131 (5)0.003 (4)0.025 (4)0.086 (5)
C44B0.093 (3)0.162 (5)0.109 (3)0.031 (3)0.001 (3)0.055 (3)
Geometric parameters (Å, º) top
O1A—C1A1.364 (3)C42A—H42A0.9300
O1A—H1A0.65 (2)C43A—C44A1.331 (6)
O3A—C7A1.291 (3)C43A—H43A0.9300
O4A—C6A1.365 (3)C44A—H44A0.9300
O4A—H4AB0.74 (3)O1B—C1B1.371 (3)
O5A—C11A1.370 (3)O1B—H1B0.77 (3)
O5A—H5A0.76 (3)O3B—C7B1.282 (3)
O7A—C17A1.275 (3)O4B—C6B1.369 (3)
O8A—C16A1.373 (3)O4B—H4BC0.83 (4)
O8A—H8A0.92 (5)O5B—C11B1.368 (3)
N1A—C22A1.286 (3)O5B—H5B0.81 (3)
N1A—C31A1.419 (4)O7B—C17B1.287 (3)
N1A—H1AN0.8600O8B—C16B1.366 (3)
N2A—C27A1.316 (3)O8B—H8B0.86 (5)
N2A—C38A1.449 (4)N1B—C22B1.291 (3)
N2A—H2AN0.8600N1B—C31B1.432 (4)
C1A—C2A1.376 (3)N1B—H1BN0.8600
C1A—C9A1.423 (3)N2B—C27B1.312 (3)
C2A—C3A1.413 (3)N2B—C38B1.452 (3)
C2A—C12A1.496 (3)N2B—H2BN0.8600
C3A—C4A1.365 (3)C1B—C2B1.383 (3)
C3A—C21A1.502 (3)C1B—C9B1.417 (3)
C4A—C10A1.403 (3)C2B—C3B1.393 (3)
C4A—H40.9300C2B—C12B1.488 (3)
C5A—C6A1.347 (4)C3B—C4B1.376 (4)
C5A—C10A1.458 (3)C3B—C21B1.503 (4)
C5A—C23A1.513 (4)C4B—C10B1.399 (4)
C6A—C7A1.425 (4)C4B—H4B0.9300
C7A—C8A1.413 (3)C5B—C6B1.336 (4)
C8A—C22A1.418 (3)C5B—C10B1.459 (3)
C8A—C9A1.447 (3)C5B—C23B1.522 (4)
C9A—C10A1.419 (3)C6B—C7B1.438 (4)
C11A—C12A1.385 (3)C7B—C8B1.411 (3)
C11A—C19A1.412 (3)C8B—C22B1.403 (4)
C12A—C13A1.415 (3)C8B—C9B1.447 (3)
C13A—C14A1.370 (3)C9B—C10B1.422 (3)
C13A—C26A1.514 (3)C11B—C12B1.388 (3)
C14A—C20A1.405 (3)C11B—C19B1.422 (3)
C14A—H14A0.9300C12B—C13B1.413 (3)
C15A—C16A1.356 (4)C13B—C14B1.372 (3)
C15A—C20A1.460 (3)C13B—C26B1.506 (4)
C15A—C28A1.519 (4)C14B—C20B1.408 (3)
C16A—C17A1.437 (4)C14B—H14B0.9300
C17A—C18A1.430 (3)C15B—C16B1.344 (4)
C18A—C27A1.402 (3)C15B—C20B1.453 (3)
C18A—C19A1.458 (3)C15B—C28B1.523 (4)
C19A—C20A1.426 (3)C16B—C17B1.444 (3)
C21A—H21A0.9600C17B—C18B1.418 (3)
C21A—H21B0.9600C18B—C27B1.410 (3)
C21A—H21C0.9600C18B—C19B1.464 (3)
C22A—H22A0.9300C19B—C20B1.420 (3)
C23A—C25A1.515 (5)C21B—H21D0.9600
C23A—C24A1.544 (4)C21B—H21F0.9600
C23A—H23A0.9800C21B—H21E0.9600
C24A—H24A0.9600C22B—H22B0.9300
C24A—H24B0.9600C23B—C24B1.476 (6)
C24A—H24C0.9600C23B—C25B1.542 (6)
C25A—H25A0.9600C23B—H23B0.9800
C25A—H25B0.9600C24B—H24D0.9600
C25A—H25C0.9600C24B—H24E0.9600
C26A—H26A0.9600C24B—H24F0.9600
C26A—H26B0.9600C25B—H25D0.9600
C26A—H26C0.9600C25B—H25E0.9600
C27A—H27A0.9300C25B—H25F0.9600
C28A—C30A1.434 (6)C26B—H26F0.9600
C28A—C30C1.488 (9)C26B—H26D0.9600
C28A—C29A1.488 (7)C26B—H26E0.9600
C28A—C29C1.581 (8)C27B—H27B0.9300
C28A—H28A0.9800C28B—C30B1.517 (4)
C28A—H28C0.9800C28B—C29B1.522 (4)
C29A—H29A0.9600C28B—H28B0.9800
C29A—H29B0.9600C29B—H29E0.9600
C29A—H29C0.9600C29B—H29D0.9600
C30A—H30A0.9600C29B—H29F0.9600
C30A—H30B0.9600C30B—H30D0.9600
C30A—H30C0.9600C30B—H30E0.9600
C29C—H29G0.9600C30B—H30F0.9600
C29C—H29H0.9600C31B—C32B1.497 (4)
C29C—H29I0.9600C31B—H31C0.9700
C30C—H30G0.9600C31B—H31D0.9700
C30C—H30H0.9600C32B—C33B1.350 (5)
C30C—H30I0.9600C32B—C37B1.378 (4)
C31A—C32A1.531 (5)C33B—C34B1.366 (5)
C31A—H31A0.9700C33B—H33B0.9300
C31A—H31B0.9700C34B—C35B1.373 (6)
C32A—C37A1.320 (5)C34B—H34B0.9300
C32A—C33A1.394 (5)C35B—C36B1.324 (5)
C33A—C34A1.346 (5)C35B—H35B0.9300
C33A—H33A0.9300C36B—C37B1.375 (4)
C34A—C35A1.315 (6)C36B—H36B0.9300
C34A—H34A0.9300C37B—H37B0.9300
C35A—C36A1.389 (7)C38B—C39B1.492 (4)
C35A—H35A0.9300C38B—H38C0.9700
C36A—C37A1.378 (6)C38B—H38D0.9700
C36A—H36A0.9300C39B—C44B1.341 (5)
C37A—H37A0.9300C39B—C40B1.358 (5)
C38A—C39A1.506 (4)C40B—C41B1.394 (7)
C38A—H38A0.9700C40B—H40B0.9300
C38A—H38B0.9700C41B—C42B1.335 (9)
C39A—C40A1.343 (5)C41B—H41B0.9300
C39A—C44A1.367 (5)C42B—C43B1.308 (8)
C40A—C41A1.392 (6)C42B—H42B0.9300
C40A—H40A0.9300C43B—C44B1.412 (7)
C41A—C42A1.349 (7)C43B—H43B0.9300
C41A—H41A0.9300C44B—H44B0.9300
C42A—C43A1.348 (8)
C1A—O1A—H1A111 (3)C40A—C41A—H41A119.7
C6A—O4A—H4AB99 (3)C43A—C42A—C41A118.9 (6)
C11A—O5A—H5A113 (2)C43A—C42A—H42A120.5
C16A—O8A—H8A101 (3)C41A—C42A—H42A120.5
C22A—N1A—C31A127.0 (3)C44A—C43A—C42A120.4 (6)
C22A—N1A—H1AN116.5C44A—C43A—H43A119.8
C31A—N1A—H1AN116.5C42A—C43A—H43A119.8
C27A—N2A—C38A123.4 (3)C43A—C44A—C39A122.5 (5)
C27A—N2A—H2AN118.3C43A—C44A—H44A118.8
C38A—N2A—H2AN118.3C39A—C44A—H44A118.8
O1A—C1A—C2A119.7 (2)C1B—O1B—H1B107 (2)
O1A—C1A—C9A116.5 (2)C6B—O4B—H4BC102 (3)
C2A—C1A—C9A123.7 (2)C11B—O5B—H5B114 (2)
C1A—C2A—C3A118.7 (2)C16B—O8B—H8B99 (3)
C1A—C2A—C12A119.9 (2)C22B—N1B—C31B123.8 (3)
C3A—C2A—C12A121.3 (2)C22B—N1B—H1BN118.1
C4A—C3A—C2A118.6 (2)C31B—N1B—H1BN118.1
C4A—C3A—C21A120.6 (2)C27B—N2B—C38B124.5 (2)
C2A—C3A—C21A120.8 (2)C27B—N2B—H2BN117.8
C3A—C4A—C10A123.7 (2)C38B—N2B—H2BN117.8
C3A—C4A—H4118.2O1B—C1B—C2B119.1 (2)
C10A—C4A—H4118.2O1B—C1B—C9B117.3 (2)
C6A—C5A—C10A118.0 (2)C2B—C1B—C9B123.6 (2)
C6A—C5A—C23A119.8 (2)C1B—C2B—C3B119.0 (2)
C10A—C5A—C23A122.2 (2)C1B—C2B—C12B117.9 (2)
C5A—C6A—O4A121.1 (3)C3B—C2B—C12B122.9 (2)
C5A—C6A—C7A123.2 (2)C4B—C3B—C2B118.6 (2)
O4A—C6A—C7A115.8 (2)C4B—C3B—C21B121.4 (2)
O3A—C7A—C8A123.7 (2)C2B—C3B—C21B120.0 (2)
O3A—C7A—C6A116.1 (2)C3B—C4B—C10B123.7 (3)
C8A—C7A—C6A120.1 (2)C3B—C4B—H4B118.1
C7A—C8A—C22A116.7 (2)C10B—C4B—H4B118.1
C7A—C8A—C9A118.6 (2)C6B—C5B—C10B118.1 (3)
C22A—C8A—C9A124.7 (2)C6B—C5B—C23B120.8 (3)
C10A—C9A—C1A116.4 (2)C10B—C5B—C23B121.0 (3)
C10A—C9A—C8A119.1 (2)C5B—C6B—O4B122.3 (3)
C1A—C9A—C8A124.5 (2)C5B—C6B—C7B123.9 (2)
C4A—C10A—C9A118.8 (2)O4B—C6B—C7B113.8 (3)
C4A—C10A—C5A120.2 (2)O3B—C7B—C8B124.3 (3)
C9A—C10A—C5A121.0 (2)O3B—C7B—C6B116.6 (2)
O5A—C11A—C12A120.2 (2)C8B—C7B—C6B119.1 (3)
O5A—C11A—C19A116.7 (2)C22B—C8B—C7B117.1 (2)
C12A—C11A—C19A123.1 (2)C22B—C8B—C9B123.9 (2)
C11A—C12A—C13A119.0 (2)C7B—C8B—C9B119.0 (2)
C11A—C12A—C2A121.1 (2)C1B—C9B—C10B116.5 (2)
C13A—C12A—C2A119.9 (2)C1B—C9B—C8B124.1 (2)
C14A—C13A—C12A118.7 (2)C10B—C9B—C8B119.4 (2)
C14A—C13A—C26A119.9 (2)C4B—C10B—C9B118.5 (2)
C12A—C13A—C26A121.4 (2)C4B—C10B—C5B121.0 (3)
C13A—C14A—C20A123.2 (2)C9B—C10B—C5B120.5 (2)
C13A—C14A—H14A118.4O5B—C11B—C12B119.9 (2)
C20A—C14A—H14A118.4O5B—C11B—C19B117.0 (2)
C16A—C15A—C20A117.3 (2)C12B—C11B—C19B123.1 (2)
C16A—C15A—C28A120.3 (2)C11B—C12B—C13B119.3 (2)
C20A—C15A—C28A122.4 (2)C11B—C12B—C2B120.8 (2)
C15A—C16A—O8A121.6 (3)C13B—C12B—C2B119.9 (2)
C15A—C16A—C17A124.7 (2)C14B—C13B—C12B118.3 (2)
O8A—C16A—C17A113.6 (2)C14B—C13B—C26B121.0 (2)
O7A—C17A—C18A123.8 (2)C12B—C13B—C26B120.7 (2)
O7A—C17A—C16A118.2 (2)C13B—C14B—C20B123.5 (2)
C18A—C17A—C16A118.0 (2)C13B—C14B—H14B118.2
C27A—C18A—C17A117.4 (2)C20B—C14B—H14B118.2
C27A—C18A—C19A123.6 (2)C16B—C15B—C20B118.3 (2)
C17A—C18A—C19A118.7 (2)C16B—C15B—C28B122.9 (2)
C11A—C19A—C20A117.1 (2)C20B—C15B—C28B118.8 (2)
C11A—C19A—C18A123.5 (2)C15B—C16B—O8B122.9 (2)
C20A—C19A—C18A119.4 (2)C15B—C16B—C17B123.8 (2)
C14A—C20A—C19A118.7 (2)O8B—C16B—C17B113.3 (2)
C14A—C20A—C15A120.8 (2)O7B—C17B—C18B123.5 (2)
C19A—C20A—C15A120.5 (2)O7B—C17B—C16B117.2 (2)
C3A—C21A—H21A109.5C18B—C17B—C16B119.3 (2)
C3A—C21A—H21B109.5C27B—C18B—C17B117.5 (2)
H21A—C21A—H21B109.5C27B—C18B—C19B124.4 (2)
C3A—C21A—H21C109.5C17B—C18B—C19B118.0 (2)
H21A—C21A—H21C109.5C20B—C19B—C11B116.6 (2)
H21B—C21A—H21C109.5C20B—C19B—C18B119.8 (2)
N1A—C22A—C8A123.4 (3)C11B—C19B—C18B123.6 (2)
N1A—C22A—H22A118.3C14B—C20B—C19B119.0 (2)
C8A—C22A—H22A118.3C14B—C20B—C15B120.5 (2)
C5A—C23A—C25A110.5 (3)C19B—C20B—C15B120.6 (2)
C5A—C23A—C24A114.7 (3)C3B—C21B—H21D109.5
C25A—C23A—C24A111.0 (3)C3B—C21B—H21F109.5
C5A—C23A—H23A106.7H21D—C21B—H21F109.5
C25A—C23A—H23A106.7C3B—C21B—H21E109.5
C24A—C23A—H23A106.7H21D—C21B—H21E109.5
C23A—C24A—H24A109.5H21F—C21B—H21E109.5
C23A—C24A—H24B109.5N1B—C22B—C8B124.3 (3)
H24A—C24A—H24B109.5N1B—C22B—H22B117.8
C23A—C24A—H24C109.5C8B—C22B—H22B117.8
H24A—C24A—H24C109.5C24B—C23B—C5B111.1 (4)
H24B—C24A—H24C109.5C24B—C23B—C25B113.9 (4)
C23A—C25A—H25A109.5C5B—C23B—C25B114.2 (4)
C23A—C25A—H25B109.5C24B—C23B—H23B105.6
H25A—C25A—H25B109.5C5B—C23B—H23B105.6
C23A—C25A—H25C109.5C25B—C23B—H23B105.6
H25A—C25A—H25C109.5C23B—C24B—H24D109.5
H25B—C25A—H25C109.5C23B—C24B—H24E109.5
C13A—C26A—H26A109.5H24D—C24B—H24E109.5
C13A—C26A—H26B109.5C23B—C24B—H24F109.5
H26A—C26A—H26B109.5H24D—C24B—H24F109.5
C13A—C26A—H26C109.5H24E—C24B—H24F109.5
H26A—C26A—H26C109.5C23B—C25B—H25D109.5
H26B—C26A—H26C109.5C23B—C25B—H25E109.5
N2A—C27A—C18A125.4 (2)H25D—C25B—H25E109.5
N2A—C27A—H27A117.3C23B—C25B—H25F109.5
C18A—C27A—H27A117.3H25D—C25B—H25F109.5
C30A—C28A—C30C109.3 (12)H25E—C25B—H25F109.5
C30A—C28A—C29A115.9 (5)C13B—C26B—H26F109.5
C30C—C28A—C29A15.2 (12)C13B—C26B—H26D109.5
C30A—C28A—C15A119.1 (3)H26F—C26B—H26D109.5
C30C—C28A—C15A124.4 (10)C13B—C26B—H26E109.5
C29A—C28A—C15A111.1 (4)H26F—C26B—H26E109.5
C30A—C28A—C29C51.0 (5)H26D—C26B—H26E109.5
C30C—C28A—C29C118.6 (10)N2B—C27B—C18B125.2 (2)
C29A—C28A—C29C133.7 (6)N2B—C27B—H27B117.4
C15A—C28A—C29C112.7 (5)C18B—C27B—H27B117.4
C30A—C28A—H28A102.6C30B—C28B—C29B111.0 (2)
C30C—C28A—H28A91.4C30B—C28B—C15B117.6 (2)
C29A—C28A—H28A102.6C29B—C28B—C15B108.9 (2)
C15A—C28A—H28A102.6C30B—C28B—H28B106.2
C29C—C28A—H28A53.6C29B—C28B—H28B106.2
C30A—C28A—H28C46.8C15B—C28B—H28B106.2
C30C—C28A—H28C97.0C28B—C29B—H29E109.5
C29A—C28A—H28C92.1C28B—C29B—H29D109.5
C15A—C28A—H28C97.0H29E—C29B—H29D109.5
C29C—C28A—H28C97.0C28B—C29B—H29F109.5
H28A—C28A—H28C149.2H29E—C29B—H29F109.5
C28A—C29A—H29A109.5H29D—C29B—H29F109.5
C28A—C29A—H29B109.5C28B—C30B—H30D109.5
C28A—C29A—H29C109.5C28B—C30B—H30E109.5
C28A—C30A—H30A109.5H30D—C30B—H30E109.5
C28A—C30A—H30B109.5C28B—C30B—H30F109.5
C28A—C30A—H30C109.5H30D—C30B—H30F109.5
C28A—C29C—H29G109.5H30E—C30B—H30F109.5
C28A—C29C—H29H109.5N1B—C31B—C32B114.3 (3)
H29G—C29C—H29H109.5N1B—C31B—H31C108.7
C28A—C29C—H29I109.5C32B—C31B—H31C108.7
H29G—C29C—H29I109.5N1B—C31B—H31D108.7
H29H—C29C—H29I109.5C32B—C31B—H31D108.7
C28A—C30C—H30G109.5H31C—C31B—H31D107.6
C28A—C30C—H30H109.5C33B—C32B—C37B118.0 (3)
H30G—C30C—H30H109.5C33B—C32B—C31B118.0 (3)
C28A—C30C—H30I109.5C37B—C32B—C31B123.9 (3)
H30G—C30C—H30I109.5C32B—C33B—C34B121.6 (4)
H30H—C30C—H30I109.5C32B—C33B—H33B119.2
N1A—C31A—C32A115.0 (3)C34B—C33B—H33B119.2
N1A—C31A—H31A108.5C33B—C34B—C35B119.7 (4)
C32A—C31A—H31A108.5C33B—C34B—H34B120.2
N1A—C31A—H31B108.5C35B—C34B—H34B120.2
C32A—C31A—H31B108.5C36B—C35B—C34B119.2 (4)
H31A—C31A—H31B107.5C36B—C35B—H35B120.4
C37A—C32A—C33A117.5 (4)C34B—C35B—H35B120.4
C37A—C32A—C31A118.8 (4)C35B—C36B—C37B121.6 (4)
C33A—C32A—C31A123.6 (3)C35B—C36B—H36B119.2
C34A—C33A—C32A118.7 (4)C37B—C36B—H36B119.2
C34A—C33A—H33A120.7C36B—C37B—C32B119.8 (4)
C32A—C33A—H33A120.7C36B—C37B—H37B120.1
C35A—C34A—C33A124.9 (5)C32B—C37B—H37B120.1
C35A—C34A—H34A117.5N2B—C38B—C39B113.5 (2)
C33A—C34A—H34A117.5N2B—C38B—H38C108.9
C34A—C35A—C36A116.8 (5)C39B—C38B—H38C108.9
C34A—C35A—H35A121.6N2B—C38B—H38D108.9
C36A—C35A—H35A121.6C39B—C38B—H38D108.9
C37A—C36A—C35A119.0 (5)H38C—C38B—H38D107.7
C37A—C36A—H36A120.5C44B—C39B—C40B118.3 (4)
C35A—C36A—H36A120.5C44B—C39B—C38B121.6 (4)
C32A—C37A—C36A123.0 (5)C40B—C39B—C38B120.0 (3)
C32A—C37A—H37A118.5C39B—C40B—C41B120.6 (5)
C36A—C37A—H37A118.5C39B—C40B—H40B119.7
N2A—C38A—C39A113.7 (3)C41B—C40B—H40B119.7
N2A—C38A—H38A108.8C42B—C41B—C40B119.9 (7)
C39A—C38A—H38A108.8C42B—C41B—H41B120.0
N2A—C38A—H38B108.8C40B—C41B—H41B120.0
C39A—C38A—H38B108.8C43B—C42B—C41B120.4 (7)
H38A—C38A—H38B107.7C43B—C42B—H42B119.8
C40A—C39A—C44A117.8 (4)C41B—C42B—H42B119.8
C40A—C39A—C38A122.4 (3)C42B—C43B—C44B120.6 (6)
C44A—C39A—C38A119.8 (3)C42B—C43B—H43B119.7
C39A—C40A—C41A119.8 (5)C44B—C43B—H43B119.7
C39A—C40A—H40A120.1C39B—C44B—C43B120.1 (5)
C41A—C40A—H40A120.1C39B—C44B—H44B119.9
C42A—C41A—C40A120.6 (6)C43B—C44B—H44B119.9
C42A—C41A—H41A119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AN···O3A0.861.792.494 (3)138
N1B—H1BN···O3B0.861.852.531 (3)135
N2A—H2AN···O7A0.861.932.584 (3)132
N2B—H2BN···O7B0.861.892.561 (3)134
O1A—H1A···O7Bi0.65 (2)2.24 (3)2.778 (3)141 (3)
O1B—H1B···O7Aii0.77 (3)2.33 (3)2.846 (2)125 (3)
O4A—H4AB···O3A0.74 (3)2.05 (3)2.588 (3)130 (3)
O4B—H4BC···O3B0.83 (4)1.98 (4)2.568 (4)126 (4)
O5A—H5A···O3B0.76 (3)2.10 (3)2.714 (3)138 (3)
O5B—H5B···O3A0.81 (3)1.98 (3)2.645 (3)139 (3)
O8A—H8A···O1Biii0.92 (5)2.45 (5)3.290 (3)151 (4)
O8A—H8A···O7A0.92 (5)1.95 (5)2.592 (3)126 (4)
O8B—H8B···O1Aiv0.86 (5)2.40 (5)3.183 (3)151 (4)
O8B—H8B···O7B0.86 (5)1.93 (5)2.577 (3)130 (4)
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AN···O3A0.861.792.494 (3)137.9
N1B—H1BN···O3B0.861.852.531 (3)134.7
N2A—H2AN···O7A0.861.932.584 (3)132.3
N2B—H2BN···O7B0.861.892.561 (3)133.7
O1A—H1A···O7Bi0.65 (2)2.24 (3)2.778 (3)141 (3)
O1B—H1B···O7Aii0.77 (3)2.33 (3)2.846 (2)125 (3)
O4A—H4AB···O3A0.74 (3)2.05 (3)2.588 (3)130 (3)
O4B—H4BC···O3B0.83 (4)1.98 (4)2.568 (4)126 (4)
O5A—H5A···O3B0.76 (3)2.10 (3)2.714 (3)138 (3)
O5B—H5B···O3A0.81 (3)1.98 (3)2.645 (3)139 (3)
O8A—H8A···O1Biii0.92 (5)2.45 (5)3.290 (3)151 (4)
O8A—H8A···O7A0.92 (5)1.95 (5)2.592 (3)126 (4)
O8B—H8B···O1Aiv0.86 (5)2.40 (5)3.183 (3)151 (4)
O8B—H8B···O7B0.86 (5)1.93 (5)2.577 (3)130 (4)
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x1, y1/2, z+1/2.
Acknowledgements top

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study F7–T048

references
References top

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