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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o199–o200.
Published online 2007 December 6. doi:  10.1107/S1600536807063477
PMCID: PMC2915262

(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

Abstract

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 [triangle]); De Amici et al. (1990 [triangle]); Diana et al. (1985 [triangle]); Faulkner (2001 [triangle]); Gothelf & Jorgensen (1998 [triangle]); Howe & Shelton (1990 [triangle]); Jager & Muller (1985 [triangle]); Kang et al. (2000 [triangle]); Konig et al. (1990 [triangle]); Kozikowski & Stein (1982 [triangle]); Lepage et al. (1992 [triangle]). Martin et al. (1989 [triangle]); Nair et al. (1999 [triangle]); Padwa (1984 [triangle]); Xue et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o199-scheme1.jpg

Experimental

Crystal data

  • C41H31Cl4N3O3
  • M r = 755.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o199-efi1.jpg
  • 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 [triangle]) T min = 0.923, T max = 0.953
  • 7698 measured reflections
  • 7370 independent reflections
  • 3074 reflections with I > 2σ(I)
  • R int = 0.052
  • 2 standard reflections frequency: 60 min intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 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 [triangle]), 639 Friedel pairs
  • Flack parameter: 0.05 (7)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063477/ci2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063477/ci2522Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.
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.

Crystal data

C41H31Cl4N3O3F000 = 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 = 2–25º
b = 12.551 (9) ŵ = 0.37 mm1
c = 22.650 (11) ÅT = 293 (2) K
β = 105.55 (4)ºNeedle, colourless
V = 3643 (4) Å30.25 × 0.18 × 0.13 mm
Z = 4

Data collection

Nonius MACH-3 diffractometerRint = 0.052
Radiation source: fine-focus sealed tubeθmax = 25.0º
Monochromator: graphiteθmin = 2.1º
T = 293(2) Kh = 0→15
ω–2θ scansk = −1→14
Absorption correction: ψ scan(North et al., 1968)l = −26→25
Tmin = 0.923, Tmax = 0.9532 standard reflections
7698 measured reflections every 60 min
7370 independent reflections intensity decay: none
3074 reflections with I > 2σ(I)

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044  w = 1/[σ2(Fo2) + (0.0239P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max = 0.001
S = 0.99Δρmax = 0.26 e Å3
7370 reflectionsΔρmin = −0.22 e Å3
921 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 639 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.05 (7)
Secondary atom site location: difference Fourier map

Special details

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)

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)
H6B10.11051.0732−0.03920.049*
H6B20.12011.07470.03140.049*
C7A0.3800 (6)0.1536 (7)0.4382 (3)0.045 (2)
C7B−0.1079 (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)
H8B0.04040.8053−0.05960.047*
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)
H10D0.22761.1552−0.05840.105*
H10E0.27831.0587−0.08370.105*
H10F0.34781.1546−0.05230.105*
C11A0.4721 (6)0.1831 (8)0.6417 (3)0.047 (2)
C11B−0.0421 (6)0.8770 (7)0.1138 (3)0.043 (2)
C12A0.4510 (6)0.2360 (8)0.6957 (4)0.052 (2)
C12B−0.0760 (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*
C13B−0.0806 (6)1.0207 (8)0.1768 (4)0.067 (3)
H13B−0.06201.07000.15090.080*
C14A0.4911 (8)0.3715 (8)0.7730 (4)0.085 (3)
H14A0.52900.43150.79000.102*
C14B−0.1127 (6)1.0549 (9)0.2265 (4)0.076 (3)
H14B−0.11621.12760.23360.092*
C15A0.4202 (9)0.3289 (10)0.8003 (5)0.089 (4)
H15A0.40970.35920.83560.107*
C15B−0.1396 (8)0.9849 (13)0.2658 (5)0.090 (4)
H15B−0.15981.00900.29970.109*
C16A0.3662 (8)0.2431 (10)0.7751 (5)0.087 (4)
H16A0.31680.21510.79300.105*
C16B−0.1361 (8)0.8784 (12)0.2540 (5)0.096 (4)
H16B−0.15510.82970.28000.116*
C17A0.3815 (6)0.1935 (8)0.7225 (4)0.063 (3)
H17A0.34430.13250.70660.076*
C17B−0.1049 (6)0.8417 (8)0.2040 (4)0.070 (3)
H17B−0.10360.76880.19680.084*
C31A0.6800 (6)0.0071 (7)0.5988 (3)0.046 (2)
H31A0.6217−0.03280.60000.055*
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)
H33A0.8210−0.02130.53620.069*
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)
H34A0.9795−0.10720.56180.073*
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)
H36A0.9330−0.19260.72250.060*
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)
C71B−0.1767 (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*
C72B−0.2835 (7)0.8010 (8)−0.1312 (4)0.062 (3)
H72B−0.31190.8517−0.11040.075*
C73A0.1214 (6)0.0451 (9)0.3504 (4)0.067 (3)
H73A0.05100.05670.34680.081*
C73B−0.3483 (7)0.7300 (9)−0.1705 (4)0.072 (3)
H73B−0.42020.7331−0.17650.087*
C74A0.1507 (7)−0.0327 (7)0.3170 (4)0.056 (2)
H74A0.1002−0.07290.28970.068*
C74B−0.3051 (9)0.6547 (9)−0.2005 (4)0.078 (3)
H74B−0.34850.6083−0.22790.093*
C75A0.2542 (7)−0.0522 (7)0.3233 (4)0.056 (3)
H75A0.2740−0.10680.30110.068*
C75B−0.2008 (8)0.6473 (8)−0.1909 (4)0.073 (3)
H75B−0.17290.5942−0.21030.088*
C76A0.3291 (6)0.0088 (7)0.3627 (3)0.052 (3)
H76A0.3994−0.00450.36670.062*
C76B−0.1347 (6)0.7186 (7)−0.1520 (4)0.059 (2)
H76B−0.06290.7137−0.14570.071*
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*
C82B−0.0123 (6)1.0065 (6)−0.1562 (4)0.047 (2)
H82B−0.06701.0364−0.14360.056*
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)
H83B−0.02561.1051−0.22720.077*
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)
H85B0.20540.8941−0.20810.074*
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)
H92B0.37780.8776−0.03040.064*
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)
H93B0.54390.8122−0.01330.090*
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)
N2B−0.0751 (4)0.7926 (6)0.0825 (3)0.0460 (18)
N3A0.3514 (5)0.2335 (6)0.4662 (3)0.054 (2)
N3B−0.1465 (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)
O2B−0.0216 (4)0.7894 (4)0.0356 (2)0.0500 (14)
O3A0.4388 (4)0.2818 (5)0.5056 (2)0.0536 (15)
O3B−0.0621 (4)1.0063 (4)−0.0180 (2)0.0520 (15)

Atomic displacement parameters (Å2)

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, °)

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—C72B−179.4 (7)
N1A—C2A—C3A—C4A−57.1 (8)C76A—C71A—C72A—C73A0.1 (12)
N1B—C2B—C3B—C31B131.5 (8)C7A—C71A—C72A—C73A−179.0 (7)
N1B—C2B—C3B—C4B−52.6 (8)C76B—C71B—C72B—C73B−2.4 (12)
C31A—C3A—C4A—O2A−7.4 (10)C7B—C71B—C72B—C73B178.6 (7)
C2A—C3A—C4A—O2A176.0 (6)C71A—C72A—C73A—C74A−1.2 (13)
C31A—C3A—C4A—O1A107.9 (8)C71B—C72B—C73B—C74B0.6 (12)
C2A—C3A—C4A—O1A−68.8 (8)C72A—C73A—C74A—C75A1.9 (13)
C31A—C3A—C4A—C5A−131.2 (8)C72B—C73B—C74B—C75B1.9 (14)
C2A—C3A—C4A—C5A52.2 (8)C73A—C74A—C75A—C76A−1.5 (13)
C31B—C3B—C4B—O2B−11.9 (10)C73B—C74B—C75B—C76B−2.5 (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—O1B−75.7 (8)C7A—C71A—C76A—C75A179.5 (7)
C31B—C3B—C4B—C5B−137.6 (8)C72B—C71B—C76B—C75B1.8 (12)
C2B—C3B—C4B—C5B46.2 (9)C7B—C71B—C76B—C75B−179.2 (7)
O2A—C4A—C5A—O3A68.4 (8)C74B—C75B—C76B—C71B0.7 (13)
O1A—C4A—C5A—O3A−46.3 (8)C7A—C8A—C81A—C82A48.5 (10)
C3A—C4A—C5A—O3A−166.6 (6)C5A—C8A—C81A—C82A−65.5 (9)
O2A—C4A—C5A—C6A−176.1 (6)C7A—C8A—C81A—C86A−130.3 (7)
O1A—C4A—C5A—C6A69.2 (8)C5A—C8A—C81A—C86A115.7 (8)
C3A—C4A—C5A—C6A−51.1 (8)C7B—C8B—C81B—C86B−139.2 (8)
O2A—C4A—C5A—C8A−44.7 (8)C5B—C8B—C81B—C86B109.5 (8)
O1A—C4A—C5A—C8A−159.4 (5)C7B—C8B—C81B—C82B41.1 (10)
C3A—C4A—C5A—C8A80.3 (8)C5B—C8B—C81B—C82B−70.2 (9)
O2B—C4B—C5B—O3B71.4 (7)C86A—C81A—C82A—C83A0.7 (11)
O1B—C4B—C5B—O3B−42.4 (8)C8A—C81A—C82A—C83A−178.2 (7)
C3B—C4B—C5B—O3B−163.2 (6)C86B—C81B—C82B—C83B0.5 (11)
O2B—C4B—C5B—C6B−173.0 (5)C8B—C81B—C82B—C83B−179.8 (7)
O1B—C4B—C5B—C6B73.2 (7)C81A—C82A—C83A—C84A0.1 (12)
C3B—C4B—C5B—C6B−47.6 (8)C81B—C82B—C83B—C84B−1.7 (13)
O2B—C4B—C5B—C8B−41.1 (8)C82A—C83A—C84A—C85A0.5 (12)
O1B—C4B—C5B—C8B−154.9 (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—C86A−1.8 (12)
C8A—C5A—C6A—N1A−68.9 (9)Cl4—C84A—C85A—C86A−178.9 (6)
O3B—C5B—C6B—N1B174.9 (5)C83B—C84B—C85B—C86B−1.4 (12)
C4B—C5B—C6B—N1B58.8 (8)Cl7—C84B—C85B—C86B−178.9 (6)
C8B—C5B—C6B—N1B−68.1 (8)C84A—C85A—C86A—C81A2.7 (12)
N3A—C7A—C8A—C81A−114.3 (7)C84A—C85A—C86A—Cl1179.6 (6)
C71A—C7A—C8A—C81A65.6 (10)C82A—C81A—C86A—C85A−2.1 (11)
N3A—C7A—C8A—C5A10.0 (8)C8A—C81A—C86A—C85A176.8 (7)
C71A—C7A—C8A—C5A−170.0 (7)C82A—C81A—C86A—Cl1−179.0 (5)
O3A—C5A—C8A—C7A−13.7 (7)C8A—C81A—C86A—Cl1−0.1 (10)
C6A—C5A—C8A—C7A−132.7 (7)C82B—C81B—C86B—C85B0.2 (11)
C4A—C5A—C8A—C7A100.7 (6)C8B—C81B—C86B—C85B−179.4 (7)
O3A—C5A—C8A—C81A106.5 (7)C82B—C81B—C86B—Cl2−178.9 (5)
C6A—C5A—C8A—C81A−12.5 (10)C8B—C81B—C86B—Cl21.4 (10)
C4A—C5A—C8A—C81A−139.1 (6)C84B—C85B—C86B—C81B0.2 (12)
N3B—C7B—C8B—C81B−104.0 (8)C84B—C85B—C86B—Cl2179.4 (6)
C71B—C7B—C8B—C81B73.3 (10)N1A—C9A—C91A—C96A−132.5 (7)
N3B—C7B—C8B—C5B18.7 (8)C10A—C9A—C91A—C96A104.6 (8)
C71B—C7B—C8B—C5B−164.0 (7)N1A—C9A—C91A—C92A53.1 (9)
O3B—C5B—C8B—C81B94.4 (7)C10A—C9A—C91A—C92A−69.8 (9)
C6B—C5B—C8B—C81B−24.0 (10)N1B—C9B—C91B—C92B47.5 (10)
C4B—C5B—C8B—C81B−150.9 (6)C10B—C9B—C91B—C92B−74.4 (9)
O3B—C5B—C8B—C7B−24.3 (7)N1B—C9B—C91B—C96B−137.5 (7)
C6B—C5B—C8B—C7B−142.7 (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—C17A−175.4 (7)C96B—C91B—C92B—C93B−1.3 (12)
N2A—C11A—C12A—C13A178.6 (9)C9B—C91B—C92B—C93B173.8 (8)
O1A—C11A—C12A—C13A1.1 (11)C91A—C92A—C93A—C94A−2.0 (13)
N2B—C11B—C12B—C17B31.9 (13)C91B—C92B—C93B—C94B−0.1 (14)
O1B—C11B—C12B—C17B−148.9 (8)C92A—C93A—C94A—C95A0.5 (15)
N2B—C11B—C12B—C13B−147.8 (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—C96B−0.4 (15)
C11A—C12A—C13A—C14A−176.3 (8)C94A—C95A—C96A—C91A−2.3 (14)
C17B—C12B—C13B—C14B0.6 (13)C92A—C91A—C96A—C95A0.8 (12)
C11B—C12B—C13B—C14B−179.7 (7)C9A—C91A—C96A—C95A−173.8 (8)
C12A—C13A—C14A—C15A−0.5 (15)C94B—C95B—C96B—C91B−1.0 (14)
C12B—C13B—C14B—C15B0.6 (14)C92B—C91B—C96B—C95B1.8 (12)
C13A—C14A—C15A—C16A−0.3 (17)C9B—C91B—C96B—C95B−173.3 (8)
C13B—C14B—C15B—C16B−1.3 (16)C5A—C6A—N1A—C2A−62.1 (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—C9A−179.1 (6)
C11A—C12A—C17A—C16A177.4 (8)C10A—C9A—N1A—C6A−56.6 (8)
C15A—C16A—C17A—C12A−1.9 (15)C91A—C9A—N1A—C6A−178.5 (6)
C13B—C12B—C17B—C16B−1.1 (14)C10A—C9A—N1A—C2A−176.9 (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—C32A−2.4 (13)C5B—C6B—N1B—C2B−65.7 (7)
C4A—C3A—C31A—C32A−178.6 (7)C91B—C9B—N1B—C6B177.5 (6)
C2B—C3B—C31B—C32B−3.3 (14)C10B—C9B—N1B—C6B−61.5 (8)
C4B—C3B—C31B—C32B−179.1 (7)C91B—C9B—N1B—C2B57.4 (8)
C3A—C31A—C32A—C37A124.6 (9)C10B—C9B—N1B—C2B178.4 (6)
C3A—C31A—C32A—C33A−56.6 (12)C3B—C2B—N1B—C6B60.9 (7)
C3B—C31B—C32B—C37B115.8 (10)C3B—C2B—N1B—C9B−177.2 (6)
C3B—C31B—C32B—C33B−71.7 (12)O1A—C11A—N2A—O2A−0.7 (10)
C37A—C32A—C33A—C34A−2.0 (13)C12A—C11A—N2A—O2A−178.2 (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—C34B−170.5 (8)C71A—C7A—N3A—O3A178.1 (6)
C32A—C33A—C34A—C35A2.2 (13)C8A—C7A—N3A—O3A−2.0 (9)
C32B—C33B—C34B—C35B−1.2 (14)C71B—C7B—N3B—O3B178.0 (6)
C33A—C34A—C35A—C36A−2.1 (13)C8B—C7B—N3B—O3B−4.6 (9)
C33A—C34A—C35A—Cl6179.7 (7)N2A—C11A—O1A—C4A−0.3 (9)
C33B—C34B—C35B—C36B−0.9 (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—C11A−119.5 (7)
Cl6—C35A—C36A—C37A179.9 (6)C5A—C4A—O1A—C11A119.7 (6)
C34B—C35B—C36B—C37B1.7 (14)N2B—C11B—O1B—C4B−4.7 (9)
Cl8—C35B—C36B—C37B−176.3 (7)C12B—C11B—O1B—C4B176.0 (7)
C35A—C36A—C37A—C32A−1.6 (13)O2B—C4B—O1B—C11B6.5 (7)
C35A—C36A—C37A—Cl5178.8 (6)C3B—C4B—O1B—C11B−111.1 (7)
C33A—C32A—C37A—C36A1.6 (12)C5B—C4B—O1B—C11B125.7 (6)
C31A—C32A—C37A—C36A−179.5 (8)C11A—N2A—O2A—C4A1.3 (8)
C33A—C32A—C37A—Cl5−178.7 (6)O1A—C4A—O2A—N2A−1.4 (7)
C31A—C32A—C37A—Cl50.2 (11)C3A—C4A—O2A—N2A116.7 (6)
C35B—C36B—C37B—C32B−0.4 (13)C5A—C4A—O2A—N2A−119.8 (6)
C35B—C36B—C37B—Cl3−177.8 (7)C11B—N2B—O2B—C4B3.9 (8)
C33B—C32B—C37B—C36B−1.5 (12)O1B—C4B—O2B—N2B−6.4 (7)
C31B—C32B—C37B—C36B171.3 (8)C3B—C4B—O2B—N2B109.3 (6)
C33B—C32B—C37B—Cl3175.8 (6)C5B—C4B—O2B—N2B−124.5 (6)
C31B—C32B—C37B—Cl3−11.4 (11)C7A—N3A—O3A—C5A−8.0 (8)
N3A—C7A—C71A—C72A−5.4 (11)C6A—C5A—O3A—N3A140.4 (6)
C8A—C7A—C71A—C72A174.7 (7)C4A—C5A—O3A—N3A−102.1 (6)
N3A—C7A—C71A—C76A175.5 (7)C8A—C5A—O3A—N3A13.9 (7)
C8A—C7A—C71A—C76A−4.4 (12)C7B—N3B—O3B—C5B−13.1 (8)
N3B—C7B—C71B—C76B178.8 (7)C6B—C5B—O3B—N3B150.8 (5)
C8B—C7B—C71B—C76B1.6 (12)C4B—C5B—O3B—N3B−91.8 (6)
N3B—C7B—C71B—C72B−2.2 (11)C8B—C5B—O3B—N3B24.4 (7)

Hydrogen-bond geometry (Å, °)

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, y−1/2, −z; (iii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2522).

References

  • Curran, D. P. (1983). J. Am. Chem. Soc.105, 5826–5833.
  • De Amici, M., De Micheli, M. & Misani, V. (1990). Tetrahedron, 46, 1975–1986.
  • 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. [PubMed]
  • Enraf–Nonius (1994). CAD-4 EXPRESS Version 5.0. Enraf–Nonius, Delft, The Netherlands.
  • Faulkner, J. (2001). Nat. Prod. Rep.18, 1–49. [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gothelf, K. V. & Jorgensen, K. A. (1998). Chem. Rev.98, 863–910. [PubMed]
  • Harms, K. & Wocadlo, S. (1996). XCAD4 University of Marburg, Germany.
  • Howe, R. K. & Shelton, B. R. (1990). J. Org. Chem.55, 4603–4607.
  • Jager, V. & Muller, I. (1985). Tetrahedron, 41, 3519–3528.
  • 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. [PubMed]
  • Konig, G. M., Wright, A. D. & Sticher, O. (1990). J. Nat. Prod.53, 1615–1618. [PubMed]
  • Kozikowski, A. P. & Stein, P. D. (1982). J. Am. Chem. Soc.104, 4023–4024.
  • Lepage, F., Tombert, F., Cuvier, G., Marivain, A. & Gillardin, J. M. (1992). Eur. J. Med. Chem.27, 581–593.
  • Martin, S. F., Colapret, J. A., Dappen, M. S., Dupre, B. & Murphy, C. J. (1989). J. Org. Chem.54, 2209–2216.
  • Nair, V., Radhakrishnan, K. V., Sheela, K. C. & Rath, N. P. (1999). Tetrahedron, 55, 14199–14210.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Padwa, A. (1984). Editor. 1,3-Dipolar Cycloaddition Chemistry. New York: Wiley.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Xue, C., Roderick, J., Mousa, S., Olson, R. E. & DeGrado, W. F. (1998). Biorg. Med. Chem. Lett.8, 3499–3504. [PubMed]

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