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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 11| November 2013| Pages o1626-o1627

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

aNational University of Uzbekistan, Faculty of Chemistry, Vuzgorodok, Tashkent 100095, Uzbekistan, and bInstitute of Bioorganic Chemistry, Mirzo-Ulugbek St. 83, Tashkent 100125, Uzbekistan
*Correspondence e-mail: h.shuxrat81@mail.ru

(Received 3 September 2013; accepted 3 October 2013; online 9 October 2013)

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 ππ 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).

Related literature

For details of extraction and synthesis of gossypol and its derivatives, see: Kenar (2006[Kenar, J. A. (2006). J. Am. Oil Chem. Soc. 83, 269-303.]). For synthesis and biological activities, see: Polsky et al. (1989[Polsky, B., Segal, S. J., Baron, P. A., Gold, J. W., Ueno, H. & Armstrong, D. (1989). Contraception, 39, 579-587.]); Radloff et al. (1985[Radloff, R. I., Deck, L. M., Royer, R. E. & Vander Jagt, D. L. (1985). Pharmacol. Res. Commun. 18, 1063-1073.]). For formation of crystalline forms of inclusion compounds, see: Ibragimov & Talipov (1999[Ibragimov, B. T. & Talipov, S. A. (1999). J. Struct. Chem. 40, 686-704.], 2004[Ibragimov, B. T. & Talipov, S. A. (2004). Gossypol, in Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 606-614. New York: Dekker.]).

[Scheme 1]

Experimental

Crystal data
  • C44H44N2O6

  • Mr = 696.81

  • Monoclinic, P 21 /c

  • a = 9.8118 (8) Å

  • b = 29.014 (2) Å

  • c = 25.5854 (17) Å

  • β = 90.196 (6)°

  • V = 7283.6 (9) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.68 mm−1

  • T = 293 K

  • 0.6 × 0.3 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.66, Tmax = 0.88

  • 54670 measured reflections

  • 15043 independent reflections

  • 7763 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.191

  • S = 0.94

  • 15043 reflections

  • 1001 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1AN⋯O3A 0.86 1.79 2.494 (3) 138
N1B—H1BN⋯O3B 0.86 1.85 2.531 (3) 135
N2A—H2AN⋯O7A 0.86 1.93 2.584 (3) 132
N2B—H2BN⋯O7B 0.86 1.89 2.561 (3) 134
O1A—H1A⋯O7Bi 0.65 (2) 2.24 (3) 2.778 (3) 141 (3)
O1B—H1B⋯O7Aii 0.77 (3) 2.33 (3) 2.846 (2) 125 (3)
O4A—H4AB⋯O3A 0.74 (3) 2.05 (3) 2.588 (3) 130 (3)
O4B—H4BC⋯O3B 0.83 (4) 1.98 (4) 2.568 (4) 126 (4)
O5A—H5A⋯O3B 0.76 (3) 2.10 (3) 2.714 (3) 138 (3)
O5B—H5B⋯O3A 0.81 (3) 1.98 (3) 2.645 (3) 139 (3)
O8A—H8A⋯O1Biii 0.92 (5) 2.45 (5) 3.290 (3) 151 (4)
O8A—H8A⋯O7A 0.92 (5) 1.95 (5) 2.592 (3) 126 (4)
O8B—H8B⋯O1Aiv 0.86 (5) 2.40 (5) 3.183 (3) 151 (4)
O8B—H8B⋯O7B 0.86 (5) 1.93 (5) 2.577 (3) 130 (4)
Symmetry codes: (i) [-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Bruker, 1998[Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0623 restraints
wR(F2) = 0.191H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.22 e Å3
15043 reflectionsΔρmin = 0.26 e Å3
1001 parameters
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

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

References

First citationBruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationIbragimov, B. T. & Talipov, S. A. (1999). J. Struct. Chem. 40, 686–704.  Web of Science CrossRef CAS
First citationIbragimov, B. T. & Talipov, S. A. (2004). Gossypol, in Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 606-614. New York: Dekker.
First citationKenar, J. A. (2006). J. Am. Oil Chem. Soc. 83, 269–303.  Web of Science CrossRef CAS
First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
First citationPolsky, B., Segal, S. J., Baron, P. A., Gold, J. W., Ueno, H. & Armstrong, D. (1989). Contraception, 39, 579–587.  CrossRef CAS PubMed Web of Science
First citationRadloff, R. I., Deck, L. M., Royer, R. E. & Vander Jagt, D. L. (1985). Pharmacol. Res. Commun. 18, 1063–1073.  CrossRef Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 11| November 2013| Pages o1626-o1627
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds