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(5S,6S,10R)-10-(2,4-Di­chloro­phen­yl)-14-[(E)-(2,4-di­chloro­phen­yl)methyl­­idene]-3,9-di­phenyl-12-[(R)-1-phenyl­ethyl]-1,4,7-trioxa-2,8,12-tri­aza­di­spiro­[4.0.4.4]tetra­deca-2,8-diene

aDepartment of Physics, Madurai Kamaraj University, Madurai 625021, India, bSchool of Chemistry, Madurai Kamaraj University, Madurai 625021, India, and cDepartment of Physics, The Madura College, Madurai 625011, India
*Correspondence e-mail: ambujasureshj@yahoo.com

(Received 13 November 2007; accepted 26 November 2007; online 6 December 2007)

The asymmetric unit of the title compound, C41H31Cl4N3O3, contains two independent mol­ecules with almost identical geometries. The piperidine ring adopts a chair conformation in both mol­ecules, and the dihydro­isoxazole rings adopt envelope conformations. The crystal structure is stabilized by C—H⋯N hydrogen bonds and C—H⋯π inter­actions.

Related literature

For related literature, see: Curran (1983[Curran, D. P. (1983). J. Am. Chem. Soc. 105, 5826-5833.]); De Amici et al. (1990[De Amici, M., De Micheli, M. & Misani, V. (1990). Tetrahedron, 46, 1975-1986.]); Diana et al. (1985[Diana, G. D., McKinlay, M. A., Brisson, C. J., Zalay, E. S., Miralles, J. V. & Salvador, U. J. (1985). J. Med. Chem. 28, 748-752.]); Faulkner (2001[Faulkner, J. (2001). Nat. Prod. Rep. 18, 1-49.]); Gothelf & Jorgensen (1998[Gothelf, K. V. & Jorgensen, K. A. (1998). Chem. Rev. 98, 863-910.]); Howe & Shelton (1990[Howe, R. K. & Shelton, B. R. (1990). J. Org. Chem. 55, 4603-4607.]); Jager & Muller (1985[Jager, V. & Muller, I. (1985). Tetrahedron, 41, 3519-3528.]); Kang et al. (2000[Kang, Y. K., Shin, K. J., Yoo, K. H., Seo, K. J., Hong, C. Y., Lee, C., Park, S. Y., Kim, D. J. & Park, S. W. (2000). Biorg. Med. Chem. Lett. 10, 95-99.]); Konig et al. (1990[Konig, G. M., Wright, A. D. & Sticher, O. (1990). J. Nat. Prod. 53, 1615-1618.]); Kozikowski & Stein (1982[Kozikowski, A. P. & Stein, P. D. (1982). J. Am. Chem. Soc. 104, 4023-4024.]); Lepage et al. (1992[Lepage, F., Tombert, F., Cuvier, G., Marivain, A. & Gillardin, J. M. (1992). Eur. J. Med. Chem. 27, 581-593.]). Martin et al. (1989[Martin, S. F., Colapret, J. A., Dappen, M. S., Dupre, B. & Murphy, C. J. (1989). J. Org. Chem. 54, 2209-2216.]); Nair et al. (1999[Nair, V., Radhakrishnan, K. V., Sheela, K. C. & Rath, N. P. (1999). Tetrahedron, 55, 14199-14210.]); Padwa (1984[Padwa, A. (1984). Editor. 1,3-Dipolar Cycloaddition Chemistry. New York: Wiley.]); Xue et al. (1998[Xue, C., Roderick, J., Mousa, S., Olson, R. E. & DeGrado, W. F. (1998). Biorg. Med. Chem. Lett. 8, 3499-3504.]).

[Scheme 1]

Experimental

Crystal data
  • C41H31Cl4N3O3

  • Mr = 755.49

  • Monoclinic, P 21

  • a = 13.302 (6) Å

  • b = 12.551 (9) Å

  • c = 22.650 (11) Å

  • β = 105.55 (4)°

  • V = 3643 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 293 (2) K

  • 0.25 × 0.18 × 0.13 mm

Data collection
  • Nonius MACH-3 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.923, Tmax = 0.953

  • 7698 measured reflections

  • 7370 independent reflections

  • 3074 reflections with I > 2σ(I)

  • Rint = 0.052

  • 2 standard reflections frequency: 60 min intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.096

  • S = 0.99

  • 7370 reflections

  • 921 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.22 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 639 Friedel pairs

  • Flack parameter: 0.05 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10B—H10D⋯N2Bi 0.96 2.61 3.560 (10) 173
C34B—H34BCg1ii 0.93 2.68 3.495 (10) 147
C74A—H74ACg2iii 0.93 2.85 3.601 (10) 139
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{1\over 2}}, -z]; (iii) x, y-1, z. Cg1 is the centroid of the C91B–C96B ring. Cg2 is the centroid of the ring C12B–C17B ring.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.0. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

1,3-Dipolar cycloaddition reactions afford complex heterocycles with multiple stereocentres, which are useful in the construction of many natural products and pharmaceuticals (Kozikowski & Stein, 1982; Curran, 1983; Jager & Muller, 1985; Martin et al., 1989). 1,3-Dipolar cycloaddition of nitrile oxides to alkenes and α, β -unsaturated carbonyl compounds afford isoxazolines, spiroisoxazolines and dioxazoles (Padwa, 1984; Gothelf & Jorgensen, 1998; Nair et al., 1999). Isoxazolines exhibit antibacterial, antiplatelet, antiviral and anticonvulsant activities, while compounds incorporating spiroisoxazoline sub-structure have stimulated much interest in medicinal and biological chemistry, and hence the structure determination of these compounds is of paramount importance (Diana et al., 1985; De Amici et al., 1990; Howe & Shelton, 1990; Konig et al., 1990; Lepage et al., 1992; Xue et al., 1998; Kang et al., 2000; Faulkner, 2001).

The asymmetric unit of the title compound contains two independent molecules (A and B), with almost identical geometry (Fig.1 and Fig.2). The piperidine ring adopts a chair conformation in both molecules. The olefinic double bonds in molecule A and molecule B have an E configuration and the aryl rings are not coplanar with the adjacent olefinic double bond. The dioxazole ring is essentially planar in both molecules and it forms a dihedral angle of 5.1 (5)° with the attached C12—C17 phenyl ring in molecule A and the corresponding angle is 33.0 (4)° in molecule B. The dihydroisoxazole ring adopts an envelope conformation in both molecules. As a result of steric repulsions the C3—C31—C32 bond angle is widened to 128.5 (8)° in molecule A and 128.6 (8)° in B.

Crystal packing reveals that molecules B are linked by C10B—H10D···N2B (Table 1) hydrogen bonds, generating a C(9) chain along the b axis. In addition, weak C—H···π interactions are observed (Table 1).

Related literature top

For related literature, see: Curran (1983); De Amici et al. (1990); Diana et al. (1985); Faulkner (2001); Gothelf & Jorgensen (1998); Howe & Shelton (1990); Jager & Muller (1985); Kang et al. (2000); Konig et al. (1990); Kozikowski & Stein (1982); Lepage et al. (1992). Martin et al. (1989); Nair et al. (1999); Padwa (1984); Xue et al. (1998). Cg1 is the centroid of the C91B–C96B ring.

Cg2 is the centroid of the ring C12B–C17B ring.

Experimental top

To a solution of 3,5-bis[(E)-(2,4-dichlorophenyl)methylidene]-1-[(R)-1-phenylethyl]-tetrahydro-4(1H)-pyridinone (0.30 g, 0.58 mmol)in benzene (20 ml), benzohydroximoyl chloride (0.316 g, 2.33 mmol) was added and the mixture stirred at room temperature. A solution of triethylamine (0.235 g, 2.33 mmol) in benzene (5 ml) was added dropwise to the above mixture and the stirring was continued for 10 h. The progress of the reaction was monitored by thin-layer chromatography (TLC) with petrolium ether-ethyl acetate (4:1 v/v) mixture as eluent. After completion of the reaction as evident from TLC, the resulting mixture was filtered to remove the triethylamine hydrochloride, the solvent evaporated in vacuo and the residue subjected to flash column chromatography on silica gel (petrolim ether-ethyl acetate, 10:1). The product was recrystallized from ethanol.

Refinement top

H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å, and Uiso = 1.2Ueq(C) for CH2 and CH groups, and 1.5Ueq for CH3 groups. The absolute configuration expected from the starting reagents was confirmed by the refinement of the Flack (1983) parameter.

Structure description top

1,3-Dipolar cycloaddition reactions afford complex heterocycles with multiple stereocentres, which are useful in the construction of many natural products and pharmaceuticals (Kozikowski & Stein, 1982; Curran, 1983; Jager & Muller, 1985; Martin et al., 1989). 1,3-Dipolar cycloaddition of nitrile oxides to alkenes and α, β -unsaturated carbonyl compounds afford isoxazolines, spiroisoxazolines and dioxazoles (Padwa, 1984; Gothelf & Jorgensen, 1998; Nair et al., 1999). Isoxazolines exhibit antibacterial, antiplatelet, antiviral and anticonvulsant activities, while compounds incorporating spiroisoxazoline sub-structure have stimulated much interest in medicinal and biological chemistry, and hence the structure determination of these compounds is of paramount importance (Diana et al., 1985; De Amici et al., 1990; Howe & Shelton, 1990; Konig et al., 1990; Lepage et al., 1992; Xue et al., 1998; Kang et al., 2000; Faulkner, 2001).

The asymmetric unit of the title compound contains two independent molecules (A and B), with almost identical geometry (Fig.1 and Fig.2). The piperidine ring adopts a chair conformation in both molecules. The olefinic double bonds in molecule A and molecule B have an E configuration and the aryl rings are not coplanar with the adjacent olefinic double bond. The dioxazole ring is essentially planar in both molecules and it forms a dihedral angle of 5.1 (5)° with the attached C12—C17 phenyl ring in molecule A and the corresponding angle is 33.0 (4)° in molecule B. The dihydroisoxazole ring adopts an envelope conformation in both molecules. As a result of steric repulsions the C3—C31—C32 bond angle is widened to 128.5 (8)° in molecule A and 128.6 (8)° in B.

Crystal packing reveals that molecules B are linked by C10B—H10D···N2B (Table 1) hydrogen bonds, generating a C(9) chain along the b axis. In addition, weak C—H···π interactions are observed (Table 1).

For related literature, see: Curran (1983); De Amici et al. (1990); Diana et al. (1985); Faulkner (2001); Gothelf & Jorgensen (1998); Howe & Shelton (1990); Jager & Muller (1985); Kang et al. (2000); Konig et al. (1990); Kozikowski & Stein (1982); Lepage et al. (1992). Martin et al. (1989); Nair et al. (1999); Padwa (1984); Xue et al. (1998). Cg1 is the centroid of the C91B–C96B ring.

Cg2 is the centroid of the ring C12B–C17B ring.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. One of the two independent molecules (molecule A), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 25% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. One of the two independent molecules (molecule B), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 25% probability level. H atoms have been omitted for clarity.
(5S,6S,10R)-10-(2,4-Dichlorophenyl)-14-[(E)-(2,4- dichlorophenyl)methylidene]-3,9-diphenyl-12-[(R)-1-phenylethyl]- 1,4,7-trioxa-2,8,12-triazadispiro[4.0.4.4]tetradeca-2,8-diene top
Crystal data top
C41H31Cl4N3O3F(000) = 1560
Mr = 755.49Dx = 1.378 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 13.302 (6) Åθ = 2–25°
b = 12.551 (9) ŵ = 0.37 mm1
c = 22.650 (11) ÅT = 293 K
β = 105.55 (4)°Needle, colourless
V = 3643 (4) Å30.25 × 0.18 × 0.13 mm
Z = 4
Data collection top
Nonius MACH-3
diffractometer
3074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 015
Absorption correction: ψ scan
(North et al., 1968)
k = 114
Tmin = 0.923, Tmax = 0.953l = 2625
7698 measured reflections2 standard reflections every 60 min
7370 independent reflections intensity decay: none
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0239P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
7370 reflectionsΔρmax = 0.26 e Å3
921 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Flack (1983), 639 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (7)
Crystal data top
C41H31Cl4N3O3V = 3643 (4) Å3
Mr = 755.49Z = 4
Monoclinic, P21Mo Kα radiation
a = 13.302 (6) ŵ = 0.37 mm1
b = 12.551 (9) ÅT = 293 K
c = 22.650 (11) Å0.25 × 0.18 × 0.13 mm
β = 105.55 (4)°
Data collection top
Nonius MACH-3
diffractometer
3074 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.052
Tmin = 0.923, Tmax = 0.9532 standard reflections every 60 min
7698 measured reflections intensity decay: none
7370 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.096Δρmax = 0.26 e Å3
S = 0.99Δρmin = 0.22 e Å3
7370 reflectionsAbsolute structure: Flack (1983), 639 Friedel pairs
921 parametersAbsolute structure parameter: 0.05 (7)
1 restraint
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*/Ueq
C2A0.7448 (6)0.1884 (6)0.5804 (3)0.044 (2)
H2A10.74930.24170.61200.053*
H2A20.81210.15340.58790.053*
C2B0.2439 (5)0.9198 (6)0.0689 (3)0.042 (2)
H2B10.24360.97050.10120.050*
H2B20.31210.88630.07840.050*
C3A0.6623 (6)0.1075 (7)0.5832 (3)0.041 (2)
C3B0.1621 (6)0.8369 (7)0.0663 (3)0.039 (2)
C4A0.5545 (6)0.1555 (7)0.5696 (3)0.046 (2)
C4B0.0520 (6)0.8768 (7)0.0449 (3)0.045 (2)
C5A0.5307 (5)0.2178 (7)0.5086 (3)0.043 (2)
C5B0.0344 (5)0.9472 (6)0.0122 (3)0.039 (2)
C6A0.6179 (6)0.2936 (7)0.5094 (3)0.046 (2)
H6A10.60290.33120.47060.055*
H6A20.62190.34590.54150.055*
C6B0.1215 (5)1.0290 (6)0.0029 (3)0.040 (2)
H6B10.11051.07320.03920.049*
H6B20.12011.07470.03140.049*
C7A0.3800 (6)0.1536 (7)0.4382 (3)0.045 (2)
C7B0.1079 (6)0.8727 (7)0.0824 (4)0.042 (2)
C8A0.4970 (5)0.1388 (6)0.4544 (3)0.037 (2)
H8A0.51450.06610.46930.044*
C8B0.0108 (5)0.8765 (6)0.0700 (3)0.039 (2)
H8B0.04040.80530.05960.047*
C9A0.8018 (6)0.3189 (7)0.5168 (4)0.051 (2)
H9A0.80800.37090.54990.061*
C9B0.3081 (6)1.0556 (7)0.0103 (4)0.049 (2)
H9B0.30751.10930.04160.059*
C10A0.7746 (6)0.3782 (7)0.4560 (4)0.077 (3)
H10A0.71250.41950.45230.115*
H10B0.76300.32780.42290.115*
H10C0.83110.42460.45430.115*
C10B0.2886 (6)1.1112 (7)0.0518 (4)0.070 (3)
H10D0.22761.15520.05840.105*
H10E0.27831.05870.08370.105*
H10F0.34781.15460.05230.105*
C11A0.4721 (6)0.1831 (8)0.6417 (3)0.047 (2)
C11B0.0421 (6)0.8770 (7)0.1138 (3)0.043 (2)
C12A0.4510 (6)0.2360 (8)0.6957 (4)0.052 (2)
C12B0.0760 (6)0.9107 (8)0.1653 (4)0.045 (2)
C13A0.5074 (7)0.3262 (9)0.7204 (4)0.069 (3)
H13A0.55540.35590.70190.082*
C13B0.0806 (6)1.0207 (8)0.1768 (4)0.067 (3)
H13B0.06201.07000.15090.080*
C14A0.4911 (8)0.3715 (8)0.7730 (4)0.085 (3)
H14A0.52900.43150.79000.102*
C14B0.1127 (6)1.0549 (9)0.2265 (4)0.076 (3)
H14B0.11621.12760.23360.092*
C15A0.4202 (9)0.3289 (10)0.8003 (5)0.089 (4)
H15A0.40970.35920.83560.107*
C15B0.1396 (8)0.9849 (13)0.2658 (5)0.090 (4)
H15B0.15981.00900.29970.109*
C16A0.3662 (8)0.2431 (10)0.7751 (5)0.087 (4)
H16A0.31680.21510.79300.105*
C16B0.1361 (8)0.8784 (12)0.2540 (5)0.096 (4)
H16B0.15510.82970.28000.116*
C17A0.3815 (6)0.1935 (8)0.7225 (4)0.063 (3)
H17A0.34430.13250.70660.076*
C17B0.1049 (6)0.8417 (8)0.2040 (4)0.070 (3)
H17B0.10360.76880.19680.084*
C31A0.6800 (6)0.0071 (7)0.5988 (3)0.046 (2)
H31A0.62170.03280.60000.055*
C31B0.1801 (6)0.7363 (7)0.0844 (3)0.053 (2)
H31B0.12120.69490.08200.064*
C32A0.7818 (6)0.0515 (7)0.6149 (4)0.048 (2)
C32B0.2813 (6)0.6817 (6)0.1076 (4)0.042 (2)
C33A0.8438 (7)0.0550 (7)0.5740 (3)0.057 (3)
H33A0.82100.02130.53620.069*
C33B0.3431 (6)0.6561 (7)0.0694 (4)0.056 (2)
H33B0.32610.68270.02960.067*
C34A0.9375 (7)0.1072 (7)0.5887 (4)0.060 (3)
H34A0.97950.10720.56180.073*
C34B0.4300 (7)0.5915 (8)0.0894 (4)0.068 (3)
H34B0.47070.57350.06330.082*
C35A0.9690 (6)0.1605 (7)0.6447 (4)0.054 (2)
C35B0.4549 (6)0.5545 (7)0.1489 (5)0.062 (3)
C36A0.9103 (6)0.1583 (6)0.6848 (4)0.050 (2)
H36A0.93300.19260.72250.060*
C36B0.3974 (7)0.5809 (8)0.1887 (4)0.058 (2)
H36B0.41570.55710.22900.070*
C37A0.8167 (6)0.1051 (7)0.6696 (3)0.046 (2)
C37B0.3120 (6)0.6436 (7)0.1663 (4)0.048 (2)
C71A0.3001 (6)0.0902 (7)0.3964 (3)0.039 (2)
C71B0.1767 (6)0.7966 (7)0.1227 (3)0.043 (2)
C72A0.1961 (7)0.1077 (7)0.3899 (4)0.056 (2)
H72A0.17530.16190.41210.067*
C72B0.2835 (7)0.8010 (8)0.1312 (4)0.062 (3)
H72B0.31190.85170.11040.075*
C73A0.1214 (6)0.0451 (9)0.3504 (4)0.067 (3)
H73A0.05100.05670.34680.081*
C73B0.3483 (7)0.7300 (9)0.1705 (4)0.072 (3)
H73B0.42020.73310.17650.087*
C74A0.1507 (7)0.0327 (7)0.3170 (4)0.056 (2)
H74A0.10020.07290.28970.068*
C74B0.3051 (9)0.6547 (9)0.2005 (4)0.078 (3)
H74B0.34850.60830.22790.093*
C75A0.2542 (7)0.0522 (7)0.3233 (4)0.056 (3)
H75A0.27400.10680.30110.068*
C75B0.2008 (8)0.6473 (8)0.1909 (4)0.073 (3)
H75B0.17290.59420.21030.088*
C76A0.3291 (6)0.0088 (7)0.3627 (3)0.052 (3)
H76A0.39940.00450.36670.062*
C76B0.1347 (6)0.7186 (7)0.1520 (4)0.059 (2)
H76B0.06290.71370.14570.071*
C81A0.5389 (5)0.1586 (6)0.3992 (3)0.0343 (19)
C81B0.0419 (6)0.9192 (7)0.1235 (4)0.043 (2)
C82A0.5102 (6)0.2491 (7)0.3633 (3)0.050 (2)
H82A0.46630.29890.37400.060*
C82B0.0123 (6)1.0065 (6)0.1562 (4)0.047 (2)
H82B0.06701.03640.14360.056*
C83A0.5454 (6)0.2664 (7)0.3123 (3)0.051 (2)
H83A0.52550.32740.28880.062*
C83B0.0132 (6)1.0487 (8)0.2060 (4)0.064 (3)
H83B0.02561.10510.22720.077*
C84A0.6094 (6)0.1939 (8)0.2964 (3)0.053 (2)
C84B0.0942 (7)1.0091 (9)0.2247 (4)0.063 (3)
C85A0.6396 (6)0.1031 (7)0.3295 (3)0.046 (2)
H85A0.68190.05310.31760.055*
C85B0.1506 (7)0.9227 (8)0.1950 (4)0.062 (3)
H85B0.20540.89410.20810.074*
C86A0.6058 (5)0.0880 (6)0.3808 (3)0.041 (2)
C86B0.1226 (6)0.8801 (6)0.1448 (3)0.046 (2)
C91A0.9062 (6)0.2626 (7)0.5259 (4)0.047 (2)
C91B0.4147 (6)1.0043 (7)0.0253 (4)0.045 (2)
C92A0.9181 (7)0.1753 (8)0.4907 (4)0.057 (2)
H92A0.86020.14700.46240.069*
C92B0.4330 (7)0.9131 (7)0.0037 (4)0.054 (2)
H92B0.37780.87760.03040.064*
C93A1.0149 (8)0.1304 (8)0.4974 (4)0.080 (3)
H93A1.02150.07060.47440.096*
C93B0.5328 (8)0.8741 (8)0.0066 (5)0.075 (3)
H93B0.54390.81220.01330.090*
C94A1.1030 (8)0.1734 (10)0.5381 (5)0.083 (3)
H94A1.16840.14310.54220.100*
C94B0.6155 (9)0.9233 (10)0.0450 (5)0.085 (4)
H94B0.68240.89610.05090.102*
C95A1.0924 (8)0.2594 (10)0.5714 (5)0.086 (3)
H95A1.15100.28970.59800.103*
C95B0.5995 (7)1.0142 (9)0.0755 (4)0.074 (3)
H95B0.65521.04880.10220.089*
C96A0.9953 (7)0.3029 (8)0.5665 (4)0.065 (3)
H96A0.98940.36080.59100.079*
C96B0.4992 (7)1.0529 (7)0.0654 (4)0.054 (2)
H96B0.48811.11360.08640.064*
Cl10.64483 (17)0.02951 (19)0.42243 (9)0.0663 (7)
Cl20.19462 (16)0.7703 (2)0.10886 (10)0.0697 (7)
Cl30.24123 (17)0.6809 (2)0.21877 (10)0.0753 (8)
Cl40.65079 (16)0.2120 (2)0.23013 (9)0.0729 (8)
Cl50.73986 (17)0.1046 (2)0.72106 (9)0.0732 (8)
Cl61.08791 (18)0.2274 (2)0.66324 (10)0.0768 (8)
Cl70.1266 (2)1.0614 (3)0.28807 (11)0.1020 (10)
Cl80.56087 (19)0.4679 (2)0.17350 (12)0.1020 (10)
N1A0.7191 (5)0.2401 (5)0.5198 (3)0.0442 (18)
N1B0.2240 (4)0.9766 (5)0.0091 (3)0.0394 (16)
N2A0.4279 (5)0.1012 (6)0.6167 (3)0.054 (2)
N2B0.0751 (4)0.7926 (6)0.0825 (3)0.0460 (18)
N3A0.3514 (5)0.2335 (6)0.4662 (3)0.054 (2)
N3B0.1465 (5)0.9463 (6)0.0560 (3)0.054 (2)
O1A0.5491 (4)0.2254 (4)0.6190 (2)0.0480 (15)
O1B0.0286 (4)0.9362 (4)0.0949 (2)0.0491 (15)
O2A0.4750 (4)0.0771 (4)0.5682 (2)0.0495 (14)
O2B0.0216 (4)0.7894 (4)0.0356 (2)0.0500 (14)
O3A0.4388 (4)0.2818 (5)0.5056 (2)0.0536 (15)
O3B0.0621 (4)1.0063 (4)0.0180 (2)0.0520 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2A0.050 (5)0.042 (6)0.038 (5)0.003 (5)0.009 (4)0.008 (5)
C2B0.044 (5)0.030 (5)0.054 (5)0.009 (4)0.019 (4)0.006 (4)
C3A0.056 (6)0.035 (6)0.035 (5)0.004 (5)0.018 (4)0.001 (4)
C3B0.045 (6)0.037 (6)0.037 (5)0.010 (5)0.014 (4)0.000 (4)
C4A0.052 (6)0.042 (6)0.045 (5)0.021 (5)0.016 (5)0.015 (5)
C4B0.038 (5)0.042 (6)0.058 (6)0.012 (5)0.019 (4)0.021 (5)
C5A0.038 (5)0.043 (5)0.052 (5)0.004 (5)0.019 (4)0.005 (5)
C5B0.039 (5)0.028 (5)0.049 (5)0.013 (4)0.012 (4)0.002 (4)
C6A0.057 (6)0.032 (6)0.046 (5)0.002 (5)0.009 (4)0.011 (4)
C6B0.050 (5)0.020 (5)0.054 (5)0.011 (4)0.018 (4)0.005 (4)
C7A0.039 (5)0.047 (6)0.051 (5)0.012 (5)0.014 (4)0.002 (5)
C7B0.046 (5)0.028 (5)0.051 (5)0.008 (5)0.012 (4)0.000 (4)
C8A0.036 (5)0.040 (5)0.034 (4)0.009 (4)0.008 (4)0.002 (4)
C8B0.033 (5)0.035 (5)0.049 (5)0.010 (4)0.009 (4)0.003 (4)
C9A0.057 (6)0.042 (6)0.059 (6)0.009 (5)0.022 (5)0.001 (5)
C9B0.050 (5)0.035 (6)0.069 (6)0.014 (5)0.025 (5)0.006 (5)
C10A0.065 (6)0.069 (7)0.101 (8)0.002 (6)0.031 (6)0.039 (6)
C10B0.063 (6)0.045 (7)0.104 (8)0.003 (5)0.023 (5)0.031 (6)
C11A0.031 (5)0.073 (8)0.041 (5)0.006 (5)0.020 (4)0.003 (5)
C11B0.033 (5)0.055 (7)0.045 (5)0.005 (5)0.016 (4)0.003 (5)
C12A0.042 (5)0.069 (8)0.045 (5)0.002 (5)0.013 (5)0.004 (5)
C12B0.042 (5)0.056 (7)0.041 (5)0.009 (5)0.016 (4)0.006 (5)
C13A0.078 (7)0.084 (8)0.052 (6)0.002 (7)0.032 (6)0.004 (6)
C13B0.067 (7)0.069 (9)0.065 (7)0.001 (6)0.020 (6)0.008 (6)
C14A0.111 (9)0.073 (9)0.077 (8)0.003 (7)0.037 (7)0.017 (7)
C14B0.060 (7)0.091 (9)0.078 (8)0.024 (6)0.019 (6)0.026 (7)
C15A0.125 (11)0.090 (10)0.067 (7)0.014 (8)0.050 (8)0.032 (7)
C15B0.057 (7)0.165 (15)0.052 (7)0.001 (9)0.019 (5)0.019 (9)
C16A0.090 (8)0.108 (11)0.085 (8)0.030 (8)0.060 (7)0.005 (8)
C16B0.078 (8)0.144 (13)0.084 (9)0.037 (9)0.051 (7)0.001 (9)
C17A0.062 (6)0.069 (7)0.068 (6)0.007 (6)0.034 (5)0.008 (6)
C17B0.066 (7)0.081 (8)0.068 (7)0.024 (6)0.027 (6)0.009 (6)
C31A0.063 (6)0.036 (6)0.038 (5)0.011 (5)0.011 (4)0.001 (4)
C31B0.051 (6)0.061 (7)0.047 (5)0.014 (5)0.012 (5)0.002 (5)
C32A0.044 (5)0.053 (7)0.039 (5)0.006 (5)0.002 (5)0.002 (5)
C32B0.043 (5)0.027 (5)0.049 (5)0.002 (4)0.001 (4)0.005 (4)
C33A0.066 (6)0.058 (7)0.041 (5)0.000 (6)0.002 (5)0.017 (5)
C33B0.061 (6)0.051 (6)0.061 (6)0.007 (5)0.026 (5)0.004 (5)
C34A0.063 (6)0.071 (7)0.049 (6)0.002 (6)0.016 (5)0.007 (6)
C34B0.061 (6)0.078 (8)0.068 (7)0.029 (6)0.023 (5)0.008 (6)
C35A0.060 (6)0.052 (6)0.048 (5)0.004 (5)0.011 (5)0.013 (5)
C35B0.045 (6)0.052 (7)0.086 (7)0.013 (5)0.008 (6)0.003 (6)
C36A0.065 (6)0.032 (5)0.049 (5)0.006 (5)0.008 (5)0.021 (4)
C36B0.066 (6)0.061 (7)0.045 (5)0.009 (6)0.008 (5)0.009 (5)
C37A0.060 (6)0.043 (6)0.033 (5)0.005 (5)0.009 (4)0.000 (5)
C37B0.044 (5)0.049 (6)0.048 (5)0.004 (5)0.010 (4)0.001 (5)
C71A0.041 (5)0.035 (6)0.042 (5)0.006 (5)0.011 (4)0.011 (5)
C71B0.034 (5)0.047 (6)0.046 (5)0.001 (5)0.006 (4)0.009 (5)
C72A0.047 (6)0.050 (6)0.070 (6)0.020 (5)0.014 (5)0.008 (5)
C72B0.047 (6)0.068 (8)0.062 (6)0.005 (6)0.002 (5)0.013 (6)
C73A0.037 (6)0.082 (8)0.075 (7)0.000 (6)0.003 (5)0.008 (6)
C73B0.051 (6)0.094 (10)0.063 (7)0.027 (7)0.002 (5)0.029 (6)
C74A0.067 (7)0.044 (6)0.054 (6)0.004 (6)0.009 (5)0.008 (5)
C74B0.088 (9)0.066 (8)0.064 (7)0.031 (8)0.005 (7)0.012 (6)
C75A0.059 (6)0.049 (7)0.066 (6)0.008 (6)0.025 (5)0.005 (5)
C75B0.080 (8)0.051 (7)0.076 (7)0.010 (7)0.001 (6)0.001 (6)
C76A0.035 (5)0.065 (7)0.051 (6)0.006 (5)0.004 (5)0.008 (5)
C76B0.054 (6)0.048 (6)0.070 (6)0.008 (6)0.007 (5)0.004 (6)
C81A0.031 (4)0.038 (5)0.032 (5)0.005 (4)0.003 (4)0.001 (4)
C81B0.038 (5)0.037 (6)0.056 (6)0.000 (5)0.017 (5)0.006 (5)
C82A0.056 (6)0.046 (7)0.046 (5)0.006 (5)0.013 (5)0.007 (5)
C82B0.056 (6)0.033 (6)0.061 (6)0.003 (5)0.029 (5)0.000 (5)
C83A0.063 (6)0.046 (6)0.044 (5)0.013 (5)0.012 (5)0.019 (5)
C83B0.052 (6)0.064 (7)0.073 (7)0.004 (6)0.012 (5)0.008 (6)
C84A0.057 (6)0.064 (7)0.041 (5)0.008 (6)0.022 (5)0.007 (5)
C84B0.061 (7)0.073 (9)0.058 (6)0.027 (6)0.022 (6)0.010 (6)
C85A0.047 (5)0.049 (6)0.048 (5)0.003 (5)0.024 (4)0.002 (5)
C85B0.056 (6)0.073 (8)0.062 (6)0.022 (6)0.025 (5)0.032 (6)
C86A0.044 (5)0.041 (6)0.040 (5)0.010 (5)0.012 (4)0.006 (4)
C86B0.037 (5)0.042 (6)0.049 (5)0.005 (5)0.003 (4)0.007 (5)
C91A0.055 (6)0.039 (6)0.054 (6)0.002 (5)0.030 (5)0.000 (5)
C91B0.038 (5)0.044 (6)0.052 (5)0.002 (5)0.012 (5)0.015 (5)
C92A0.061 (6)0.055 (7)0.060 (6)0.001 (6)0.024 (5)0.001 (5)
C92B0.047 (6)0.041 (6)0.074 (7)0.002 (5)0.016 (5)0.001 (5)
C93A0.073 (7)0.074 (9)0.105 (9)0.008 (7)0.043 (7)0.011 (7)
C93B0.077 (7)0.050 (8)0.099 (9)0.004 (7)0.023 (7)0.008 (6)
C94A0.062 (7)0.093 (10)0.101 (9)0.034 (8)0.032 (7)0.036 (8)
C94B0.070 (8)0.082 (10)0.107 (10)0.014 (8)0.029 (8)0.036 (8)
C95A0.057 (7)0.102 (10)0.101 (8)0.001 (7)0.027 (6)0.002 (8)
C95B0.039 (6)0.097 (10)0.078 (8)0.014 (7)0.001 (6)0.019 (7)
C96A0.072 (7)0.067 (8)0.060 (6)0.002 (7)0.021 (6)0.006 (6)
C96B0.056 (6)0.048 (6)0.053 (6)0.014 (6)0.007 (5)0.006 (5)
Cl10.0870 (17)0.0475 (16)0.0696 (15)0.0249 (14)0.0300 (13)0.0126 (14)
Cl20.0575 (14)0.0606 (17)0.0890 (17)0.0147 (14)0.0160 (13)0.0193 (16)
Cl30.0742 (16)0.089 (2)0.0697 (15)0.0038 (16)0.0318 (13)0.0080 (15)
Cl40.0707 (15)0.094 (2)0.0623 (15)0.0114 (16)0.0325 (13)0.0181 (15)
Cl50.0824 (17)0.085 (2)0.0567 (15)0.0028 (16)0.0262 (14)0.0154 (15)
Cl60.0818 (17)0.0712 (18)0.0769 (16)0.0228 (16)0.0205 (14)0.0162 (16)
Cl70.127 (2)0.110 (3)0.0870 (19)0.045 (2)0.0584 (18)0.0013 (18)
Cl80.092 (2)0.091 (2)0.119 (2)0.043 (2)0.0213 (17)0.018 (2)
N1A0.039 (4)0.050 (5)0.043 (4)0.008 (4)0.012 (3)0.007 (4)
N1B0.037 (4)0.034 (4)0.048 (4)0.003 (4)0.013 (3)0.001 (4)
N2A0.053 (5)0.060 (6)0.052 (5)0.010 (4)0.018 (4)0.007 (4)
N2B0.043 (4)0.044 (5)0.053 (4)0.008 (4)0.016 (4)0.005 (4)
N3A0.048 (4)0.058 (6)0.057 (5)0.014 (4)0.014 (4)0.004 (4)
N3B0.052 (5)0.043 (5)0.063 (5)0.004 (4)0.009 (4)0.003 (4)
O1A0.054 (3)0.049 (4)0.045 (3)0.008 (3)0.022 (3)0.015 (3)
O1B0.056 (3)0.041 (4)0.057 (4)0.020 (3)0.025 (3)0.017 (3)
O2A0.054 (3)0.049 (4)0.049 (3)0.014 (3)0.021 (3)0.014 (3)
O2B0.050 (3)0.044 (4)0.059 (3)0.012 (3)0.020 (3)0.009 (3)
O3A0.057 (4)0.045 (4)0.057 (4)0.010 (3)0.011 (3)0.019 (3)
O3B0.048 (3)0.039 (4)0.070 (4)0.007 (3)0.018 (3)0.004 (3)
Geometric parameters (Å, º) top
C2A—N1A1.474 (8)C32B—C33B1.382 (9)
C2A—C3A1.508 (10)C33A—C34A1.368 (9)
C2A—H2A10.97C33A—H33A0.93
C2A—H2A20.97C33B—C34B1.385 (10)
C2B—N1B1.491 (8)C33B—H33B0.93
C2B—C3B1.495 (9)C34A—C35A1.394 (10)
C2B—H2B10.97C34A—H34A0.93
C2B—H2B20.97C34B—C35B1.380 (11)
C3A—C31A1.312 (10)C34B—H34B0.93
C3A—C4A1.509 (10)C35A—C36A1.348 (9)
C3B—C31B1.329 (10)C35A—Cl61.740 (8)
C3B—C4B1.500 (10)C35B—C36B1.370 (10)
C4A—O2A1.438 (8)C35B—Cl81.749 (9)
C4A—O1A1.438 (8)C36A—C37A1.373 (10)
C4A—C5A1.546 (10)C36A—H36A0.93
C4B—O2B1.447 (8)C36B—C37B1.363 (10)
C4B—O1B1.456 (8)C36B—H36B0.93
C4B—C5B1.532 (9)C37A—Cl51.745 (7)
C5A—O3A1.449 (8)C37B—Cl31.766 (7)
C5A—C6A1.496 (9)C71A—C72A1.369 (9)
C5A—C8A1.548 (9)C71A—C76A1.391 (10)
C5B—O3B1.458 (7)C71B—C76B1.382 (10)
C5B—C6B1.520 (9)C71B—C72B1.383 (9)
C5B—C8B1.542 (9)C72A—C73A1.389 (10)
C6A—N1A1.465 (8)C72A—H72A0.93
C6A—H6A10.97C72B—C73B1.386 (11)
C6A—H6A20.97C72B—H72B0.93
C6B—N1B1.473 (8)C73A—C74A1.355 (11)
C6B—H6B10.97C73A—H73A0.93
C6B—H6B20.97C73B—C74B1.377 (12)
C7A—N3A1.297 (9)C73B—H73B0.93
C7A—C71A1.456 (10)C74A—C75A1.368 (9)
C7A—C8A1.512 (9)C74A—H74A0.93
C7B—N3B1.279 (9)C74B—C75B1.348 (11)
C7B—C71B1.461 (10)C74B—H74B0.93
C7B—C8B1.529 (9)C75A—C76A1.377 (9)
C8A—C81A1.518 (8)C75A—H75A0.93
C8A—H8A0.98C75B—C76B1.390 (10)
C8B—C81B1.482 (9)C75B—H75B0.93
C8B—H8B0.98C76A—H76A0.93
C9A—N1A1.495 (8)C76B—H76B0.93
C9A—C10A1.522 (9)C81A—C82A1.389 (10)
C9A—C91A1.523 (10)C81A—C86A1.396 (9)
C9A—H9A0.98C81B—C86B1.379 (9)
C9B—N1B1.488 (9)C81B—C82B1.408 (10)
C9B—C91B1.511 (10)C82A—C83A1.376 (9)
C9B—C10B1.529 (9)C82A—H82A0.93
C9B—H9B0.98C82B—C83B1.369 (10)
C10A—H10A0.96C82B—H82B0.93
C10A—H10B0.96C83A—C84A1.358 (10)
C10A—H10C0.96C83A—H83A0.93
C10B—H10D0.96C83B—C84B1.354 (10)
C10B—H10E0.96C83B—H83B0.93
C10B—H10F0.96C84A—C85A1.365 (11)
C11A—N2A1.243 (10)C84A—Cl41.747 (8)
C11A—O1A1.370 (8)C84B—C85B1.385 (11)
C11A—C12A1.482 (11)C84B—Cl71.734 (9)
C11B—N2B1.285 (9)C85A—C86A1.367 (9)
C11B—O1B1.357 (8)C85A—H85A0.93
C11B—C12B1.422 (10)C85B—C86B1.395 (10)
C12A—C17A1.346 (10)C85B—H85B0.93
C12A—C13A1.389 (11)C86A—Cl11.753 (8)
C12B—C17B1.359 (11)C86B—Cl21.750 (8)
C12B—C13B1.409 (11)C91A—C96A1.385 (10)
C13A—C14A1.388 (11)C91A—C92A1.390 (11)
C13A—H13A0.93C91B—C92B1.374 (10)
C13B—C14B1.376 (11)C91B—C96B1.383 (10)
C13B—H13B0.93C92A—C93A1.377 (10)
C14A—C15A1.367 (12)C92A—H92A0.93
C14A—H14A0.93C92B—C93B1.375 (10)
C14B—C15B1.364 (14)C92B—H92B0.93
C14B—H14B0.93C93A—C94A1.391 (12)
C15A—C16A1.335 (13)C93A—H93A0.93
C15A—H15A0.93C93B—C94B1.355 (12)
C15B—C16B1.366 (15)C93B—H93B0.93
C15B—H15B0.93C94A—C95A1.346 (13)
C16A—C17A1.406 (11)C94A—H94A0.93
C16A—H16A0.93C94B—C95B1.378 (13)
C16B—C17B1.387 (12)C94B—H94B0.93
C16B—H16B0.93C95A—C96A1.379 (11)
C17A—H17A0.93C95A—H95A0.93
C17B—H17B0.93C95B—C96B1.379 (11)
C31A—C32A1.498 (10)C95B—H95B0.93
C31A—H31A0.93C96A—H96A0.93
C31B—C32B1.475 (10)C96B—H96B0.93
C31B—H31B0.93N2A—O2A1.435 (7)
C32A—C37A1.376 (9)N2B—O2B1.429 (7)
C32A—C33A1.396 (9)N3A—O3A1.400 (7)
C32B—C37B1.367 (9)N3B—O3B1.432 (7)
N1A—C2A—C3A110.2 (6)C32A—C33A—H33A119.5
N1A—C2A—H2A1109.6C32B—C33B—C34B121.1 (8)
C3A—C2A—H2A1109.6C32B—C33B—H33B119.5
N1A—C2A—H2A2109.6C34B—C33B—H33B119.5
C3A—C2A—H2A2109.6C33A—C34A—C35A118.8 (8)
H2A1—C2A—H2A2108.1C33A—C34A—H34A120.6
N1B—C2B—C3B110.3 (6)C35A—C34A—H34A120.6
N1B—C2B—H2B1109.6C35B—C34B—C33B118.5 (8)
C3B—C2B—H2B1109.6C35B—C34B—H34B120.8
N1B—C2B—H2B2109.6C33B—C34B—H34B120.8
C3B—C2B—H2B2109.6C36A—C35A—C34A121.1 (8)
H2B1—C2B—H2B2108.1C36A—C35A—Cl6120.0 (7)
C31A—C3A—C2A125.3 (8)C34A—C35A—Cl6118.9 (7)
C31A—C3A—C4A122.0 (8)C36B—C35B—C34B122.1 (8)
C2A—C3A—C4A112.7 (7)C36B—C35B—Cl8119.1 (8)
C31B—C3B—C2B125.4 (8)C34B—C35B—Cl8118.8 (7)
C31B—C3B—C4B119.7 (8)C35A—C36A—C37A119.3 (7)
C2B—C3B—C4B114.7 (7)C35A—C36A—H36A120.4
O2A—C4A—O1A104.2 (5)C37A—C36A—H36A120.4
O2A—C4A—C3A112.6 (7)C37B—C36B—C35B116.8 (8)
O1A—C4A—C3A109.2 (6)C37B—C36B—H36B121.6
O2A—C4A—C5A110.6 (6)C35B—C36B—H36B121.6
O1A—C4A—C5A110.2 (6)C36A—C37A—C32A121.9 (7)
C3A—C4A—C5A109.9 (6)C36A—C37A—Cl5119.2 (6)
O2B—C4B—O1B103.0 (5)C32A—C37A—Cl5118.9 (7)
O2B—C4B—C3B111.0 (7)C36B—C37B—C32B124.5 (7)
O1B—C4B—C3B108.3 (6)C36B—C37B—Cl3116.3 (7)
O2B—C4B—C5B111.6 (6)C32B—C37B—Cl3119.1 (7)
O1B—C4B—C5B110.1 (6)C72A—C71A—C76A118.7 (8)
C3B—C4B—C5B112.3 (6)C72A—C71A—C7A121.5 (8)
O3A—C5A—C6A106.9 (7)C76A—C71A—C7A119.8 (7)
O3A—C5A—C4A106.9 (6)C76B—C71B—C72B119.6 (8)
C6A—C5A—C4A109.7 (6)C76B—C71B—C7B119.9 (7)
O3A—C5A—C8A104.9 (6)C72B—C71B—C7B120.5 (8)
C6A—C5A—C8A118.4 (6)C71A—C72A—C73A120.4 (8)
C4A—C5A—C8A109.3 (6)C71A—C72A—H72A119.8
O3B—C5B—C6B106.8 (6)C73A—C72A—H72A119.8
O3B—C5B—C4B107.5 (6)C71B—C72B—C73B120.2 (9)
C6B—C5B—C4B109.5 (6)C71B—C72B—H72B119.9
O3B—C5B—C8B104.0 (5)C73B—C72B—H72B119.9
C6B—C5B—C8B118.7 (6)C74A—C73A—C72A120.3 (8)
C4B—C5B—C8B109.6 (6)C74A—C73A—H73A119.8
N1A—C6A—C5A112.7 (7)C72A—C73A—H73A119.8
N1A—C6A—H6A1109.0C74B—C73B—C72B119.3 (9)
C5A—C6A—H6A1109.0C74B—C73B—H73B120.4
N1A—C6A—H6A2109.0C72B—C73B—H73B120.4
C5A—C6A—H6A2109.0C73A—C74A—C75A120.2 (9)
H6A1—C6A—H6A2107.8C73A—C74A—H74A119.9
N1B—C6B—C5B111.0 (6)C75A—C74A—H74A119.9
N1B—C6B—H6B1109.4C75B—C74B—C73B120.9 (10)
C5B—C6B—H6B1109.4C75B—C74B—H74B119.5
N1B—C6B—H6B2109.4C73B—C74B—H74B119.5
C5B—C6B—H6B2109.4C74A—C75A—C76A120.1 (8)
H6B1—C6B—H6B2108.0C74A—C75A—H75A120.0
N3A—C7A—C71A118.8 (7)C76A—C75A—H75A120.0
N3A—C7A—C8A113.3 (7)C74B—C75B—C76B120.5 (10)
C71A—C7A—C8A128.0 (7)C74B—C75B—H75B119.7
N3B—C7B—C71B120.1 (8)C76B—C75B—H75B119.7
N3B—C7B—C8B114.5 (7)C75A—C76A—C71A120.3 (8)
C71B—C7B—C8B125.3 (7)C75A—C76A—H76A119.8
C7A—C8A—C81A111.2 (6)C71A—C76A—H76A119.8
C7A—C8A—C5A100.0 (6)C71B—C76B—C75B119.4 (8)
C81A—C8A—C5A117.1 (6)C71B—C76B—H76B120.3
C7A—C8A—H8A109.4C75B—C76B—H76B120.3
C81A—C8A—H8A109.4C82A—C81A—C86A116.1 (7)
C5A—C8A—H8A109.4C82A—C81A—C8A120.8 (7)
C81B—C8B—C7B111.2 (6)C86A—C81A—C8A123.1 (7)
C81B—C8B—C5B116.6 (7)C86B—C81B—C82B115.4 (7)
C7B—C8B—C5B98.1 (6)C86B—C81B—C8B124.9 (8)
C81B—C8B—H8B110.1C82B—C81B—C8B119.7 (7)
C7B—C8B—H8B110.1C83A—C82A—C81A121.3 (8)
C5B—C8B—H8B110.1C83A—C82A—H82A119.4
N1A—C9A—C10A111.4 (6)C81A—C82A—H82A119.4
N1A—C9A—C91A110.0 (7)C83B—C82B—C81B122.0 (8)
C10A—C9A—C91A109.7 (6)C83B—C82B—H82B119.0
N1A—C9A—H9A108.6C81B—C82B—H82B119.0
C10A—C9A—H9A108.6C84A—C83A—C82A119.7 (8)
C91A—C9A—H9A108.6C84A—C83A—H83A120.2
N1B—C9B—C91B112.1 (7)C82A—C83A—H83A120.2
N1B—C9B—C10B110.2 (6)C84B—C83B—C82B120.6 (9)
C91B—C9B—C10B108.5 (6)C84B—C83B—H83B119.7
N1B—C9B—H9B108.7C82B—C83B—H83B119.7
C91B—C9B—H9B108.7C83A—C84A—C85A121.8 (7)
C10B—C9B—H9B108.7C83A—C84A—Cl4120.3 (8)
C9A—C10A—H10A109.5C85A—C84A—Cl4117.8 (7)
C9A—C10A—H10B109.5C83B—C84B—C85B120.5 (9)
H10A—C10A—H10B109.5C83B—C84B—Cl7121.0 (9)
C9A—C10A—H10C109.5C85B—C84B—Cl7118.4 (8)
H10A—C10A—H10C109.5C84A—C85A—C86A117.8 (7)
H10B—C10A—H10C109.5C84A—C85A—H85A121.1
C9B—C10B—H10D109.5C86A—C85A—H85A121.1
C9B—C10B—H10E109.5C84B—C85B—C86B117.9 (8)
H10D—C10B—H10E109.5C84B—C85B—H85B121.1
C9B—C10B—H10F109.5C86B—C85B—H85B121.1
H10D—C10B—H10F109.5C85A—C86A—C81A123.2 (7)
H10E—C10B—H10F109.5C85A—C86A—Cl1117.1 (6)
N2A—C11A—O1A117.3 (7)C81A—C86A—Cl1119.6 (6)
N2A—C11A—C12A125.2 (8)C81B—C86B—C85B123.5 (8)
O1A—C11A—C12A117.5 (8)C81B—C86B—Cl2119.9 (7)
N2B—C11B—O1B116.1 (7)C85B—C86B—Cl2116.6 (7)
N2B—C11B—C12B124.2 (8)C96A—C91A—C92A117.4 (8)
O1B—C11B—C12B119.7 (8)C96A—C91A—C9A120.5 (8)
C17A—C12A—C13A120.2 (9)C92A—C91A—C9A121.9 (8)
C17A—C12A—C11A120.0 (9)C92B—C91B—C96B117.7 (8)
C13A—C12A—C11A119.8 (8)C92B—C91B—C9B121.6 (8)
C17B—C12B—C13B118.2 (9)C96B—C91B—C9B120.6 (8)
C17B—C12B—C11B123.0 (9)C93A—C92A—C91A120.4 (9)
C13B—C12B—C11B118.8 (9)C93A—C92A—H92A119.8
C12A—C13A—C14A119.2 (9)C91A—C92A—H92A119.8
C12A—C13A—H13A120.4C91B—C92B—C93B120.1 (9)
C14A—C13A—H13A120.4C91B—C92B—H92B120.0
C14B—C13B—C12B119.6 (10)C93B—C92B—H92B120.0
C14B—C13B—H13B120.2C92A—C93A—C94A120.8 (10)
C12B—C13B—H13B120.2C92A—C93A—H93A119.6
C15A—C14A—C13A120.8 (10)C94A—C93A—H93A119.6
C15A—C14A—H14A119.6C94B—C93B—C92B121.8 (10)
C13A—C14A—H14A119.6C94B—C93B—H93B119.1
C15B—C14B—C13B121.7 (11)C92B—C93B—H93B119.1
C15B—C14B—H14B119.1C95A—C94A—C93A119.1 (10)
C13B—C14B—H14B119.1C95A—C94A—H94A120.5
C16A—C15A—C14A118.7 (10)C93A—C94A—H94A120.5
C16A—C15A—H15A120.7C93B—C94B—C95B119.4 (11)
C14A—C15A—H15A120.7C93B—C94B—H94B120.3
C14B—C15B—C16B118.3 (11)C95B—C94B—H94B120.3
C14B—C15B—H15B120.8C94A—C95A—C96A120.6 (11)
C16B—C15B—H15B120.8C94A—C95A—H95A119.7
C15A—C16A—C17A122.4 (10)C96A—C95A—H95A119.7
C15A—C16A—H16A118.8C94B—C95B—C96B118.7 (10)
C17A—C16A—H16A118.8C94B—C95B—H95B120.6
C15B—C16B—C17B121.2 (11)C96B—C95B—H95B120.6
C15B—C16B—H16B119.4C95A—C96A—C91A121.7 (9)
C17B—C16B—H16B119.4C95A—C96A—H96A119.2
C12A—C17A—C16A118.6 (10)C91A—C96A—H96A119.2
C12A—C17A—H17A120.7C95B—C96B—C91B122.2 (9)
C16A—C17A—H17A120.7C95B—C96B—H96B118.9
C12B—C17B—C16B120.9 (10)C91B—C96B—H96B118.9
C12B—C17B—H17B119.6C6A—N1A—C2A109.0 (6)
C16B—C17B—H17B119.6C6A—N1A—C9A110.2 (6)
C3A—C31A—C32A128.4 (8)C2A—N1A—C9A110.1 (6)
C3A—C31A—H31A115.8C6B—N1B—C9B111.1 (6)
C32A—C31A—H31A115.8C6B—N1B—C2B108.1 (5)
C3B—C31B—C32B128.5 (8)C9B—N1B—C2B110.6 (6)
C3B—C31B—H31B115.7C11A—N2A—O2A105.9 (6)
C32B—C31B—H31B115.7C11B—N2B—O2B105.7 (6)
C37A—C32A—C33A117.7 (8)C7A—N3A—O3A110.1 (6)
C37A—C32A—C31A121.6 (8)C7B—N3B—O3B108.3 (6)
C33A—C32A—C31A120.7 (7)C11A—O1A—C4A104.7 (6)
C37B—C32B—C33B117.0 (7)C11B—O1B—C4B106.0 (6)
C37B—C32B—C31B121.1 (7)N2A—O2A—C4A107.9 (5)
C33B—C32B—C31B121.5 (7)N2B—O2B—C4B108.8 (5)
C34A—C33A—C32A121.1 (8)N3A—O3A—C5A109.6 (6)
C34A—C33A—H33A119.5N3B—O3B—C5B108.4 (5)
N1A—C2A—C3A—C31A126.3 (8)C8B—C7B—C71B—C72B179.4 (7)
N1A—C2A—C3A—C4A57.1 (8)C76A—C71A—C72A—C73A0.1 (12)
N1B—C2B—C3B—C31B131.5 (8)C7A—C71A—C72A—C73A179.0 (7)
N1B—C2B—C3B—C4B52.6 (8)C76B—C71B—C72B—C73B2.4 (12)
C31A—C3A—C4A—O2A7.4 (10)C7B—C71B—C72B—C73B178.6 (7)
C2A—C3A—C4A—O2A176.0 (6)C71A—C72A—C73A—C74A1.2 (13)
C31A—C3A—C4A—O1A107.9 (8)C71B—C72B—C73B—C74B0.6 (12)
C2A—C3A—C4A—O1A68.8 (8)C72A—C73A—C74A—C75A1.9 (13)
C31A—C3A—C4A—C5A131.2 (8)C72B—C73B—C74B—C75B1.9 (14)
C2A—C3A—C4A—C5A52.2 (8)C73A—C74A—C75A—C76A1.5 (13)
C31B—C3B—C4B—O2B11.9 (10)C73B—C74B—C75B—C76B2.5 (14)
C2B—C3B—C4B—O2B171.9 (6)C74A—C75A—C76A—C71A0.4 (12)
C31B—C3B—C4B—O1B100.5 (8)C72A—C71A—C76A—C75A0.3 (11)
C2B—C3B—C4B—O1B75.7 (8)C7A—C71A—C76A—C75A179.5 (7)
C31B—C3B—C4B—C5B137.6 (8)C72B—C71B—C76B—C75B1.8 (12)
C2B—C3B—C4B—C5B46.2 (9)C7B—C71B—C76B—C75B179.2 (7)
O2A—C4A—C5A—O3A68.4 (8)C74B—C75B—C76B—C71B0.7 (13)
O1A—C4A—C5A—O3A46.3 (8)C7A—C8A—C81A—C82A48.5 (10)
C3A—C4A—C5A—O3A166.6 (6)C5A—C8A—C81A—C82A65.5 (9)
O2A—C4A—C5A—C6A176.1 (6)C7A—C8A—C81A—C86A130.3 (7)
O1A—C4A—C5A—C6A69.2 (8)C5A—C8A—C81A—C86A115.7 (8)
C3A—C4A—C5A—C6A51.1 (8)C7B—C8B—C81B—C86B139.2 (8)
O2A—C4A—C5A—C8A44.7 (8)C5B—C8B—C81B—C86B109.5 (8)
O1A—C4A—C5A—C8A159.4 (5)C7B—C8B—C81B—C82B41.1 (10)
C3A—C4A—C5A—C8A80.3 (8)C5B—C8B—C81B—C82B70.2 (9)
O2B—C4B—C5B—O3B71.4 (7)C86A—C81A—C82A—C83A0.7 (11)
O1B—C4B—C5B—O3B42.4 (8)C8A—C81A—C82A—C83A178.2 (7)
C3B—C4B—C5B—O3B163.2 (6)C86B—C81B—C82B—C83B0.5 (11)
O2B—C4B—C5B—C6B173.0 (5)C8B—C81B—C82B—C83B179.8 (7)
O1B—C4B—C5B—C6B73.2 (7)C81A—C82A—C83A—C84A0.1 (12)
C3B—C4B—C5B—C6B47.6 (8)C81B—C82B—C83B—C84B1.7 (13)
O2B—C4B—C5B—C8B41.1 (8)C82A—C83A—C84A—C85A0.5 (12)
O1B—C4B—C5B—C8B154.9 (5)C82A—C83A—C84A—Cl4177.5 (6)
C3B—C4B—C5B—C8B84.3 (8)C82B—C83B—C84B—C85B2.2 (13)
O3A—C5A—C6A—N1A173.1 (5)C82B—C83B—C84B—Cl7179.6 (6)
C4A—C5A—C6A—N1A57.6 (8)C83A—C84A—C85A—C86A1.8 (12)
C8A—C5A—C6A—N1A68.9 (9)Cl4—C84A—C85A—C86A178.9 (6)
O3B—C5B—C6B—N1B174.9 (5)C83B—C84B—C85B—C86B1.4 (12)
C4B—C5B—C6B—N1B58.8 (8)Cl7—C84B—C85B—C86B178.9 (6)
C8B—C5B—C6B—N1B68.1 (8)C84A—C85A—C86A—C81A2.7 (12)
N3A—C7A—C8A—C81A114.3 (7)C84A—C85A—C86A—Cl1179.6 (6)
C71A—C7A—C8A—C81A65.6 (10)C82A—C81A—C86A—C85A2.1 (11)
N3A—C7A—C8A—C5A10.0 (8)C8A—C81A—C86A—C85A176.8 (7)
C71A—C7A—C8A—C5A170.0 (7)C82A—C81A—C86A—Cl1179.0 (5)
O3A—C5A—C8A—C7A13.7 (7)C8A—C81A—C86A—Cl10.1 (10)
C6A—C5A—C8A—C7A132.7 (7)C82B—C81B—C86B—C85B0.2 (11)
C4A—C5A—C8A—C7A100.7 (6)C8B—C81B—C86B—C85B179.4 (7)
O3A—C5A—C8A—C81A106.5 (7)C82B—C81B—C86B—Cl2178.9 (5)
C6A—C5A—C8A—C81A12.5 (10)C8B—C81B—C86B—Cl21.4 (10)
C4A—C5A—C8A—C81A139.1 (6)C84B—C85B—C86B—C81B0.2 (12)
N3B—C7B—C8B—C81B104.0 (8)C84B—C85B—C86B—Cl2179.4 (6)
C71B—C7B—C8B—C81B73.3 (10)N1A—C9A—C91A—C96A132.5 (7)
N3B—C7B—C8B—C5B18.7 (8)C10A—C9A—C91A—C96A104.6 (8)
C71B—C7B—C8B—C5B164.0 (7)N1A—C9A—C91A—C92A53.1 (9)
O3B—C5B—C8B—C81B94.4 (7)C10A—C9A—C91A—C92A69.8 (9)
C6B—C5B—C8B—C81B24.0 (10)N1B—C9B—C91B—C92B47.5 (10)
C4B—C5B—C8B—C81B150.9 (6)C10B—C9B—C91B—C92B74.4 (9)
O3B—C5B—C8B—C7B24.3 (7)N1B—C9B—C91B—C96B137.5 (7)
C6B—C5B—C8B—C7B142.7 (7)C10B—C9B—C91B—C96B100.6 (8)
C4B—C5B—C8B—C7B90.5 (7)C96A—C91A—C92A—C93A1.3 (11)
N2A—C11A—C12A—C17A2.1 (13)C9A—C91A—C92A—C93A175.8 (8)
O1A—C11A—C12A—C17A175.4 (7)C96B—C91B—C92B—C93B1.3 (12)
N2A—C11A—C12A—C13A178.6 (9)C9B—C91B—C92B—C93B173.8 (8)
O1A—C11A—C12A—C13A1.1 (11)C91A—C92A—C93A—C94A2.0 (13)
N2B—C11B—C12B—C17B31.9 (13)C91B—C92B—C93B—C94B0.1 (14)
O1B—C11B—C12B—C17B148.9 (8)C92A—C93A—C94A—C95A0.5 (15)
N2B—C11B—C12B—C13B147.8 (9)C92B—C93B—C94B—C95B1.0 (15)
O1B—C11B—C12B—C13B31.4 (11)C93A—C94A—C95A—C96A1.5 (15)
C17A—C12A—C13A—C14A0.1 (13)C93B—C94B—C95B—C96B0.4 (15)
C11A—C12A—C13A—C14A176.3 (8)C94A—C95A—C96A—C91A2.3 (14)
C17B—C12B—C13B—C14B0.6 (13)C92A—C91A—C96A—C95A0.8 (12)
C11B—C12B—C13B—C14B179.7 (7)C9A—C91A—C96A—C95A173.8 (8)
C12A—C13A—C14A—C15A0.5 (15)C94B—C95B—C96B—C91B1.0 (14)
C12B—C13B—C14B—C15B0.6 (14)C92B—C91B—C96B—C95B1.8 (12)
C13A—C14A—C15A—C16A0.3 (17)C9B—C91B—C96B—C95B173.3 (8)
C13B—C14B—C15B—C16B1.3 (16)C5A—C6A—N1A—C2A62.1 (8)
C14A—C15A—C16A—C17A1.5 (17)C5A—C6A—N1A—C9A177.0 (6)
C14B—C15B—C16B—C17B0.8 (18)C3A—C2A—N1A—C6A59.9 (8)
C13A—C12A—C17A—C16A1.0 (13)C3A—C2A—N1A—C9A179.1 (6)
C11A—C12A—C17A—C16A177.4 (8)C10A—C9A—N1A—C6A56.6 (8)
C15A—C16A—C17A—C12A1.9 (15)C91A—C9A—N1A—C6A178.5 (6)
C13B—C12B—C17B—C16B1.1 (14)C10A—C9A—N1A—C2A176.9 (6)
C11B—C12B—C17B—C16B179.2 (8)C91A—C9A—N1A—C2A61.3 (8)
C15B—C16B—C17B—C12B0.4 (16)C5B—C6B—N1B—C9B172.8 (6)
C2A—C3A—C31A—C32A2.4 (13)C5B—C6B—N1B—C2B65.7 (7)
C4A—C3A—C31A—C32A178.6 (7)C91B—C9B—N1B—C6B177.5 (6)
C2B—C3B—C31B—C32B3.3 (14)C10B—C9B—N1B—C6B61.5 (8)
C4B—C3B—C31B—C32B179.1 (7)C91B—C9B—N1B—C2B57.4 (8)
C3A—C31A—C32A—C37A124.6 (9)C10B—C9B—N1B—C2B178.4 (6)
C3A—C31A—C32A—C33A56.6 (12)C3B—C2B—N1B—C6B60.9 (7)
C3B—C31B—C32B—C37B115.8 (10)C3B—C2B—N1B—C9B177.2 (6)
C3B—C31B—C32B—C33B71.7 (12)O1A—C11A—N2A—O2A0.7 (10)
C37A—C32A—C33A—C34A2.0 (13)C12A—C11A—N2A—O2A178.2 (7)
C31A—C32A—C33A—C34A179.2 (8)O1B—C11B—N2B—O2B0.6 (9)
C37B—C32B—C33B—C34B2.3 (12)C12B—C11B—N2B—O2B179.8 (7)
C31B—C32B—C33B—C34B170.5 (8)C71A—C7A—N3A—O3A178.1 (6)
C32A—C33A—C34A—C35A2.2 (13)C8A—C7A—N3A—O3A2.0 (9)
C32B—C33B—C34B—C35B1.2 (14)C71B—C7B—N3B—O3B178.0 (6)
C33A—C34A—C35A—C36A2.1 (13)C8B—C7B—N3B—O3B4.6 (9)
C33A—C34A—C35A—Cl6179.7 (7)N2A—C11A—O1A—C4A0.3 (9)
C33B—C34B—C35B—C36B0.9 (15)C12A—C11A—O1A—C4A177.4 (7)
C33B—C34B—C35B—Cl8177.1 (7)O2A—C4A—O1A—C11A1.0 (7)
C34A—C35A—C36A—C37A1.7 (13)C3A—C4A—O1A—C11A119.5 (7)
Cl6—C35A—C36A—C37A179.9 (6)C5A—C4A—O1A—C11A119.7 (6)
C34B—C35B—C36B—C37B1.7 (14)N2B—C11B—O1B—C4B4.7 (9)
Cl8—C35B—C36B—C37B176.3 (7)C12B—C11B—O1B—C4B176.0 (7)
C35A—C36A—C37A—C32A1.6 (13)O2B—C4B—O1B—C11B6.5 (7)
C35A—C36A—C37A—Cl5178.8 (6)C3B—C4B—O1B—C11B111.1 (7)
C33A—C32A—C37A—C36A1.6 (12)C5B—C4B—O1B—C11B125.7 (6)
C31A—C32A—C37A—C36A179.5 (8)C11A—N2A—O2A—C4A1.3 (8)
C33A—C32A—C37A—Cl5178.7 (6)O1A—C4A—O2A—N2A1.4 (7)
C31A—C32A—C37A—Cl50.2 (11)C3A—C4A—O2A—N2A116.7 (6)
C35B—C36B—C37B—C32B0.4 (13)C5A—C4A—O2A—N2A119.8 (6)
C35B—C36B—C37B—Cl3177.8 (7)C11B—N2B—O2B—C4B3.9 (8)
C33B—C32B—C37B—C36B1.5 (12)O1B—C4B—O2B—N2B6.4 (7)
C31B—C32B—C37B—C36B171.3 (8)C3B—C4B—O2B—N2B109.3 (6)
C33B—C32B—C37B—Cl3175.8 (6)C5B—C4B—O2B—N2B124.5 (6)
C31B—C32B—C37B—Cl311.4 (11)C7A—N3A—O3A—C5A8.0 (8)
N3A—C7A—C71A—C72A5.4 (11)C6A—C5A—O3A—N3A140.4 (6)
C8A—C7A—C71A—C72A174.7 (7)C4A—C5A—O3A—N3A102.1 (6)
N3A—C7A—C71A—C76A175.5 (7)C8A—C5A—O3A—N3A13.9 (7)
C8A—C7A—C71A—C76A4.4 (12)C7B—N3B—O3B—C5B13.1 (8)
N3B—C7B—C71B—C76B178.8 (7)C6B—C5B—O3B—N3B150.8 (5)
C8B—C7B—C71B—C76B1.6 (12)C4B—C5B—O3B—N3B91.8 (6)
N3B—C7B—C71B—C72B2.2 (11)C8B—C5B—O3B—N3B24.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10B—H10D···N2Bi0.962.613.560 (10)173
C34B—H34B···Cg1ii0.932.683.495 (10)147
C74A—H74A···Cg2iii0.932.853.601 (10)139
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y1/2, z; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC41H31Cl4N3O3
Mr755.49
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)13.302 (6), 12.551 (9), 22.650 (11)
β (°) 105.55 (4)
V3)3643 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.25 × 0.18 × 0.13
Data collection
DiffractometerNonius MACH-3
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.923, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections
7698, 7370, 3074
Rint0.052
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.096, 0.99
No. of reflections7370
No. of parameters921
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.22
Absolute structureFlack (1983), 639 Friedel pairs
Absolute structure parameter0.05 (7)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10B—H10D···N2Bi0.962.613.560 (10)173
C34B—H34B···Cg1ii0.932.683.495 (10)147
C74A—H74A···Cg2iii0.932.853.601 (10)139
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y1/2, z; (iii) x, y1, z.
 

Acknowledgements

SP thanks CSIR, New Delhi, for a Major Research Project.

References

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