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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o139.
Published online 2009 December 16. doi:  10.1107/S1600536809053276
PMCID: PMC2980235

1′-Benzyl-4,4′′-bis­(4-chloro­phen­yl)-3-(2,6-dichloro­phen­yl)-1′′-methyl-4,5-dihydro­isoxazole-5-spiro-3′-piperidine-5′-spiro-3′′-pyrrolidine-2′′-spiro-3′′′-indoline-2′′′,4′-dione

Abstract

The asymmetric unit of the title compound, C43H34Cl4N4O3, contains two crystallographically independent mol­ecules. In both mol­ecules, the pyrrolidine ring adopts a twist conformation, the oxindole units are slightly distorted from planarity and the isoxazoline ring adopts an envelope conformation. The crystal structure is stabilized by N—H(...)O hydrogen-bonding inter­actions giving one-dimensional chain structures.

Related literature

For the biological activity of spiro compounds, see: James et al. (1991 [triangle]); Kobayashi et al. (1991 [triangle]). For the use of 1,3-dipolar cyclo­addition reactions in the construction of spiro compounds, see: Caramella & Grunanger (1984 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o139-scheme1.jpg

Experimental

Crystal data

  • C43H34Cl4N4O3
  • M r = 796.54
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o139-efi1.jpg
  • a = 25.588 (5) Å
  • b = 8.8028 (18) Å
  • c = 33.195 (7) Å
  • V = 7477 (3) Å3
  • Z = 8
  • Cu Kα radiation
  • μ = 3.26 mm−1
  • T = 113 K
  • 0.38 × 0.20 × 0.18 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2001 [triangle]) T min = 0.371, T max = 0.592
  • 35641 measured reflections
  • 12162 independent reflections
  • 10126 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.128
  • S = 1.00
  • 12162 reflections
  • 982 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.68 e Å−3
  • Δρmin = −0.65 e Å−3
  • Absolute structure: Flack (1983), 4589 Friedel pairs
  • Flack parameter: 0.187 (12)

Data collection: CrystalClear (Rigaku, 2001 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053276/zs2026sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053276/zs2026Isup2.hkl

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

supplementary crystallographic information

Comment

Spiro-compounds represent an important class of naturally occurring substances, which in many cases exhibit useful biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are widely used for the construction of spiro-compounds (Caramella & Grunanger,1984). In this paper, the structure of the synthetic title compound C43H34Cl4N4O3 (I) is reported. In (I) the asymmetric unit contains two crystallographically independent spiro molecules (Fig. 1). In both molecules, the pyrrolidine ring adopts a twist conformation, the oxindole moieties are slightly distorted from planarity and the isoxazoline ring adopts an envelope conformation. The molecular structure is stabilized by intermolecular N—H···O hydrogen-bonding interactions (Table 1) giving one-dimensional chain structures. The absolute configuration for (I) was not confirmed in this analysis, the Flack parameter (Flack, 1983) [0.187 (12): 4589 Friedel pairs] for the configuration reported [C1,C44(S, C3,C46R, C6,C49R, C27,C70(S, C29,C72(S)] being inconclusive.

Experimental

A mixture of 1''-Benzyl-5''-(4-chlorobenzylidene)-4'-(4-chlorophenyl)-1'-methyl-2,3-\ dihydro-1H-indole-3-spiro-2'-pyrrolidine-3'-spiro-3''-piperidine-2,\ 3''-dione (1 mmol) and 2,6-dichloro-benzonitrile oxide (1.5 mmol) were dissolved in dry benzene (30 ml) and heated under reflux for 24 h. After completion of the reaction as indicated by TLC, the solvent was evaporated under vacuum. The residue was purified by column chromatography employing a petroleum ether/ethyl acetate mixture (5:1 v/v) as eluent, to obtain the title compound (I). A 20 mg sample of (I) was dissolved in 15 ml of a petroleum ether-ethyl acetate mixture which was allowed to evaporate at room temperature over 15 days, giving colorless single crystals suitable for X-ray analysis.

Refinement

All H atoms attached to C were fixed geometrically and treated as riding with C—H = 0.95 Å (aromatic), 0.98 Å (methyl), 0.99 Å (methylene), 1.00 Å (methine) with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methane C). The H atoms on N4 and N8 were located in a difference Fourier and both positional and isotropic displacement parameters were refined. The absolute configuration for both molecules [C1, C44(S, C3, C46R, C6, C49R, C27, C70(S, C29, C72(S)], as indicated by the Flack parameter [0.187 (12): 4589 Friedel pairs], was not conclusive but was adopted as a better alternative to that for the enantiomer.

Figures

Fig. 1.
The molecular structure of (I) with the atom-labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Crystal data

C43H34Cl4N4O3Dx = 1.415 Mg m3
Mr = 796.54Melting point: 515 K
Orthorhombic, Pca21Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2c -2acCell parameters from 8065 reflections
a = 25.588 (5) Åθ = 27.6–72.7°
b = 8.8028 (18) ŵ = 3.26 mm1
c = 33.195 (7) ÅT = 113 K
V = 7477 (3) Å3Prism, colorless
Z = 80.38 × 0.20 × 0.18 mm
F(000) = 3296

Data collection

Rigaku Saturn CCD area-detector diffractometer12162 independent reflections
Radiation source: fine-focus sealed tube10126 reflections with I > 2σ(I)
graphiteRint = 0.059
Detector resolution: 11.11 pixels mm-1θmax = 72.7°, θmin = 2.7°
ω and [var phi] scansh = −31→31
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)k = −7→10
Tmin = 0.371, Tmax = 0.592l = −40→33
35641 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128w = 1/[σ2(Fo2) + (0.0763P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
12162 reflectionsΔρmax = 0.68 e Å3
982 parametersΔρmin = −0.65 e Å3
1 restraintAbsolute structure: Flack (1983), 4589 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.187 (12)

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
Cl10.40006 (4)1.32448 (11)0.48020 (3)0.0316 (2)
Cl20.43932 (4)0.71264 (10)0.47298 (3)0.0312 (2)
Cl30.32260 (6)1.08502 (16)0.28205 (4)0.0699 (5)
Cl40.80487 (5)1.45614 (14)0.43692 (4)0.0504 (3)
Cl50.65692 (4)0.15562 (12)0.54840 (3)0.0357 (2)
Cl60.69754 (4)0.76332 (11)0.53592 (3)0.0358 (2)
Cl70.58501 (5)0.43025 (14)0.74233 (4)0.0507 (3)
Cl81.06625 (5)0.06761 (15)0.58627 (4)0.0514 (3)
N10.49888 (11)1.1480 (3)0.46582 (8)0.0230 (6)
N20.57768 (10)1.0529 (3)0.33825 (8)0.0195 (6)
N30.65828 (12)0.6533 (4)0.38483 (9)0.0260 (7)
N40.58478 (12)0.6975 (4)0.30111 (9)0.0242 (6)
H40.5815 (17)0.697 (5)0.2750 (14)0.029*
N50.75677 (11)0.3436 (3)0.55589 (8)0.0222 (6)
N60.83536 (11)0.4556 (4)0.68193 (9)0.0223 (6)
N70.91228 (12)0.8600 (4)0.63442 (9)0.0247 (7)
N80.83980 (13)0.8136 (4)0.71811 (9)0.0252 (7)
H80.8372 (18)0.820 (5)0.7383 (15)0.030*
O10.53832 (9)1.1680 (3)0.43659 (7)0.0216 (5)
O20.57444 (9)0.8760 (3)0.44919 (7)0.0248 (5)
O30.66436 (10)0.8166 (3)0.30265 (7)0.0270 (6)
O40.79718 (9)0.3346 (3)0.58406 (7)0.0230 (5)
O50.83066 (10)0.6288 (3)0.57014 (7)0.0262 (6)
O60.91991 (10)0.6987 (3)0.71672 (7)0.0271 (6)
C10.53390 (13)1.0508 (4)0.40508 (9)0.0198 (7)
C20.57813 (13)0.9369 (4)0.41662 (10)0.0183 (7)
C30.62505 (13)0.9098 (4)0.38905 (9)0.0184 (7)
C40.62789 (13)1.0431 (5)0.35943 (10)0.0223 (7)
H4A0.63481.13880.37410.027*
H4B0.65651.02650.33990.027*
C50.54139 (13)1.1343 (4)0.36490 (10)0.0211 (7)
H5A0.50711.14480.35130.025*
H5B0.55511.23760.37020.025*
C60.48014 (13)0.9751 (4)0.41316 (9)0.0192 (7)
H60.48520.86330.41660.023*
C70.46662 (13)1.0452 (4)0.45370 (10)0.0196 (7)
C80.41806 (13)1.0165 (4)0.47611 (10)0.0223 (7)
C90.38395 (15)1.1351 (4)0.48791 (11)0.0254 (8)
C100.33538 (15)1.1067 (5)0.50485 (11)0.0283 (8)
H100.31261.18850.51120.034*
C110.32043 (15)0.9595 (5)0.51246 (11)0.0304 (9)
H110.28740.94040.52450.036*
C120.35266 (15)0.8391 (5)0.50285 (10)0.0262 (8)
H120.34240.73780.50880.031*
C130.40018 (14)0.8682 (4)0.48447 (10)0.0224 (7)
C140.43769 (13)1.0022 (4)0.38233 (9)0.0193 (7)
C150.42652 (14)0.8877 (4)0.35449 (11)0.0249 (8)
H150.44360.79220.35640.030*
C160.39001 (17)0.9140 (5)0.32358 (12)0.0356 (10)
H160.38270.83740.30420.043*
C170.36537 (17)1.0505 (5)0.32185 (13)0.0370 (10)
C180.37413 (15)1.1647 (5)0.35003 (13)0.0346 (9)
H180.35571.25830.34860.042*
C190.41041 (14)1.1385 (4)0.38032 (11)0.0251 (8)
H190.41671.21480.40000.030*
C200.58312 (14)1.1354 (5)0.29984 (10)0.0261 (8)
H20A0.61371.09410.28520.031*
H20B0.59041.24350.30580.031*
C210.53567 (14)1.1266 (4)0.27248 (10)0.0239 (8)
C220.50555 (15)0.9968 (5)0.26976 (11)0.0297 (9)
H220.51180.91440.28760.036*
C230.46609 (17)0.9858 (5)0.24113 (13)0.0370 (10)
H230.44560.89610.23950.044*
C240.45640 (17)1.1063 (6)0.21469 (12)0.0379 (10)
H240.42981.09820.19480.046*
C250.48567 (16)1.2362 (5)0.21780 (11)0.0331 (9)
H250.47911.31890.20010.040*
C260.52473 (14)1.2475 (5)0.24656 (11)0.0282 (8)
H260.54431.33880.24870.034*
C270.61786 (13)0.7504 (4)0.36647 (10)0.0203 (7)
C280.70261 (14)0.7521 (4)0.39313 (11)0.0264 (8)
H28A0.72030.78360.36800.032*
H28B0.72830.70190.41110.032*
C290.67655 (13)0.8865 (4)0.41392 (10)0.0221 (7)
H290.66590.85140.44140.027*
C300.70972 (13)1.0271 (5)0.41960 (10)0.0241 (8)
C310.75910 (14)1.0404 (5)0.40336 (12)0.0326 (9)
H310.77330.95830.38830.039*
C320.78855 (15)1.1720 (6)0.40857 (13)0.0400 (10)
H320.82241.17970.39690.048*
C330.76842 (16)1.2909 (5)0.43067 (12)0.0339 (9)
C340.71960 (16)1.2802 (5)0.44791 (12)0.0334 (9)
H340.70581.36230.46310.040*
C350.69082 (15)1.1476 (5)0.44278 (11)0.0303 (9)
H350.65761.13880.45530.036*
C360.67124 (17)0.5140 (5)0.36293 (13)0.0339 (9)
H36A0.68470.54010.33620.051*
H36B0.63980.45130.36010.051*
H36C0.69790.45730.37790.051*
C370.62585 (14)0.7643 (4)0.31973 (10)0.0242 (8)
C380.54876 (14)0.6387 (4)0.32859 (10)0.0231 (7)
C390.56571 (14)0.6681 (4)0.36807 (10)0.0217 (7)
C400.53884 (15)0.6023 (4)0.39984 (11)0.0261 (8)
H400.55070.61520.42670.031*
C410.49401 (15)0.5165 (4)0.39183 (12)0.0287 (8)
H410.47500.47270.41350.034*
C420.47716 (15)0.4949 (4)0.35261 (12)0.0276 (8)
H420.44620.43820.34770.033*
C430.50477 (15)0.5549 (4)0.32021 (11)0.0277 (8)
H430.49360.53850.29330.033*
C440.79140 (13)0.4535 (4)0.61487 (10)0.0193 (7)
C450.83470 (14)0.5699 (4)0.60303 (10)0.0201 (7)
C460.88109 (13)0.6011 (4)0.63086 (10)0.0198 (7)
C470.88525 (13)0.4686 (4)0.66056 (10)0.0224 (7)
H47A0.89290.37320.64590.027*
H47B0.91390.48740.68000.027*
C480.79913 (14)0.3729 (4)0.65574 (10)0.0228 (7)
H48A0.76490.36340.66940.027*
H48B0.81280.26920.65100.027*
C490.73631 (13)0.5233 (4)0.60600 (9)0.0190 (7)
H490.74050.63440.60060.023*
C500.72359 (13)0.4432 (4)0.56665 (10)0.0193 (7)
C510.67364 (14)0.4640 (4)0.54461 (10)0.0229 (7)
C520.63953 (15)0.3428 (5)0.53677 (11)0.0271 (8)
C530.59018 (16)0.3613 (5)0.51950 (11)0.0339 (10)
H530.56820.27650.51440.041*
C540.57427 (15)0.5080 (6)0.50999 (12)0.0400 (11)
H540.54000.52430.49980.048*
C550.60715 (16)0.6298 (5)0.51511 (11)0.0318 (9)
H550.59660.72880.50720.038*
C560.65580 (15)0.6062 (4)0.53197 (10)0.0264 (8)
C570.69461 (13)0.5022 (4)0.63777 (10)0.0196 (7)
C580.68451 (15)0.6202 (5)0.66496 (11)0.0277 (8)
H580.70140.71540.66160.033*
C590.65006 (16)0.5992 (5)0.69671 (12)0.0314 (9)
H590.64360.67890.71540.038*
C600.62538 (16)0.4612 (6)0.70081 (12)0.0354 (10)
C610.63297 (15)0.3444 (5)0.67353 (12)0.0304 (9)
H610.61450.25130.67620.037*
C620.66825 (14)0.3660 (4)0.64202 (11)0.0263 (8)
H620.67420.28640.62330.032*
C630.84205 (14)0.3750 (5)0.72034 (10)0.0242 (7)
H63A0.87160.42150.73510.029*
H63B0.85150.26820.71450.029*
C640.79431 (13)0.3761 (4)0.74757 (10)0.0229 (7)
C650.76286 (15)0.5042 (5)0.75104 (11)0.0298 (8)
H650.76890.58920.73400.036*
C660.72235 (16)0.5091 (6)0.77933 (13)0.0383 (10)
H660.70080.59670.78130.046*
C670.71373 (16)0.3854 (6)0.80454 (12)0.0374 (10)
H670.68650.38840.82400.045*
C680.74494 (16)0.2583 (5)0.80107 (12)0.0356 (10)
H680.73940.17400.81840.043*
C690.78424 (15)0.2527 (5)0.77249 (10)0.0261 (8)
H690.80470.16310.76990.031*
C700.87270 (14)0.7620 (4)0.65290 (10)0.0211 (7)
C710.95743 (14)0.7652 (5)0.62621 (11)0.0262 (8)
H71A0.97550.73550.65140.031*
H71B0.98250.81690.60810.031*
C720.93233 (13)0.6284 (4)0.60569 (10)0.0217 (7)
H720.92130.66180.57820.026*
C730.96695 (14)0.4906 (4)0.60042 (10)0.0236 (8)
C741.01649 (15)0.4805 (5)0.61742 (11)0.0319 (9)
H741.02960.56420.63240.038*
C751.04736 (16)0.3514 (5)0.61315 (12)0.0348 (10)
H751.08110.34700.62510.042*
C761.02857 (16)0.2313 (5)0.59157 (12)0.0358 (10)
C770.97972 (16)0.2368 (5)0.57354 (12)0.0350 (9)
H770.96700.15310.55840.042*
C780.94980 (15)0.3666 (5)0.57807 (11)0.0307 (9)
H780.91650.37120.56550.037*
C790.92313 (16)1.0007 (5)0.65661 (12)0.0335 (9)
H79A0.93710.97560.68330.050*
H79B0.89071.05900.65960.050*
H79C0.94881.06120.64170.050*
C800.88097 (14)0.7476 (4)0.69968 (10)0.0224 (7)
C810.80291 (15)0.8700 (4)0.69060 (10)0.0242 (8)
C820.81982 (14)0.8396 (4)0.65138 (10)0.0205 (7)
C830.79248 (15)0.9015 (4)0.61928 (10)0.0253 (8)
H830.80450.88730.59250.030*
C840.74746 (16)0.9845 (5)0.62673 (11)0.0295 (8)
H840.72821.02560.60480.035*
C850.73009 (16)1.0081 (5)0.66622 (12)0.0303 (8)
H850.69861.06230.67080.036*
C860.75858 (15)0.9528 (4)0.69889 (11)0.0268 (8)
H860.74780.97160.72580.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0311 (5)0.0255 (5)0.0383 (5)0.0028 (4)0.0114 (4)−0.0008 (4)
Cl20.0335 (5)0.0263 (5)0.0339 (4)0.0032 (4)0.0095 (4)0.0046 (4)
Cl30.0757 (9)0.0570 (8)0.0770 (9)−0.0234 (7)−0.0587 (8)0.0254 (7)
Cl40.0384 (6)0.0441 (7)0.0687 (8)−0.0124 (5)−0.0201 (5)0.0121 (6)
Cl50.0363 (5)0.0324 (5)0.0383 (5)−0.0095 (4)−0.0095 (4)0.0021 (4)
Cl60.0390 (5)0.0309 (5)0.0375 (5)−0.0006 (4)−0.0046 (4)0.0103 (4)
Cl70.0486 (6)0.0523 (7)0.0513 (6)0.0114 (5)0.0312 (5)0.0121 (5)
Cl80.0383 (6)0.0486 (7)0.0673 (7)0.0163 (5)0.0163 (5)0.0060 (6)
N10.0177 (14)0.0324 (17)0.0188 (13)0.0003 (13)0.0047 (11)−0.0002 (12)
N20.0122 (13)0.0309 (17)0.0153 (13)−0.0001 (12)−0.0013 (10)0.0037 (11)
N30.0230 (15)0.0328 (18)0.0223 (15)0.0080 (14)−0.0031 (12)0.0004 (12)
N40.0259 (15)0.0313 (18)0.0152 (14)0.0008 (14)−0.0036 (11)−0.0002 (12)
N50.0216 (15)0.0264 (16)0.0186 (13)−0.0011 (13)−0.0039 (11)−0.0037 (11)
N60.0172 (14)0.0323 (18)0.0173 (13)0.0018 (13)−0.0014 (11)0.0022 (12)
N70.0236 (15)0.0285 (17)0.0220 (14)−0.0067 (13)0.0038 (12)−0.0042 (12)
N80.0245 (15)0.0361 (19)0.0149 (13)0.0017 (14)0.0006 (12)−0.0023 (13)
O10.0162 (11)0.0264 (13)0.0221 (11)−0.0071 (10)0.0067 (9)−0.0041 (10)
O20.0234 (13)0.0345 (15)0.0166 (11)0.0050 (11)0.0012 (9)0.0066 (10)
O30.0226 (13)0.0400 (16)0.0185 (12)−0.0018 (12)0.0023 (9)−0.0023 (11)
O40.0195 (12)0.0253 (14)0.0242 (12)0.0022 (10)−0.0051 (10)−0.0067 (10)
O50.0222 (12)0.0373 (15)0.0192 (12)−0.0010 (11)−0.0009 (10)0.0030 (11)
O60.0223 (13)0.0407 (16)0.0184 (11)−0.0014 (12)−0.0015 (10)−0.0009 (10)
C10.0183 (16)0.0254 (19)0.0156 (15)0.0014 (14)0.0004 (12)0.0006 (13)
C20.0154 (16)0.0220 (18)0.0175 (15)−0.0007 (14)−0.0026 (12)0.0004 (13)
C30.0144 (15)0.0279 (19)0.0128 (14)0.0038 (14)−0.0018 (12)0.0007 (13)
C40.0160 (17)0.035 (2)0.0157 (15)−0.0017 (15)−0.0001 (12)0.0025 (14)
C50.0160 (16)0.027 (2)0.0200 (16)0.0026 (14)0.0024 (12)0.0045 (14)
C60.0198 (16)0.0199 (18)0.0180 (15)0.0036 (14)0.0023 (13)0.0004 (13)
C70.0180 (16)0.0242 (18)0.0165 (15)0.0028 (14)0.0019 (12)0.0002 (12)
C80.0154 (15)0.036 (2)0.0154 (15)−0.0058 (15)−0.0007 (12)−0.0012 (14)
C90.0267 (19)0.029 (2)0.0208 (16)−0.0013 (16)0.0011 (14)−0.0015 (14)
C100.0215 (18)0.039 (2)0.0244 (17)−0.0001 (17)0.0045 (14)−0.0091 (16)
C110.0221 (18)0.046 (2)0.0231 (18)−0.0059 (18)0.0088 (14)−0.0052 (16)
C120.0288 (19)0.032 (2)0.0178 (16)−0.0109 (16)0.0031 (14)−0.0037 (14)
C130.0229 (18)0.027 (2)0.0176 (15)0.0015 (15)−0.0004 (13)−0.0026 (13)
C140.0164 (15)0.0255 (19)0.0161 (15)−0.0011 (15)0.0011 (12)0.0008 (13)
C150.0236 (18)0.026 (2)0.0250 (17)−0.0054 (16)−0.0018 (14)0.0002 (15)
C160.036 (2)0.042 (3)0.029 (2)−0.016 (2)−0.0129 (17)−0.0025 (18)
C170.035 (2)0.036 (2)0.039 (2)−0.0099 (19)−0.0204 (18)0.0119 (18)
C180.0225 (19)0.036 (2)0.046 (2)−0.0018 (17)−0.0060 (17)0.0115 (19)
C190.0210 (17)0.028 (2)0.0267 (17)−0.0033 (16)−0.0006 (14)0.0013 (14)
C200.0227 (17)0.037 (2)0.0186 (16)−0.0016 (17)0.0018 (14)0.0080 (15)
C210.0209 (17)0.035 (2)0.0162 (15)0.0048 (16)0.0026 (13)0.0037 (14)
C220.0254 (19)0.036 (2)0.0282 (18)−0.0026 (18)−0.0064 (15)0.0049 (16)
C230.035 (2)0.040 (3)0.036 (2)−0.003 (2)−0.0102 (18)0.0049 (18)
C240.029 (2)0.057 (3)0.0271 (18)0.005 (2)−0.0114 (16)0.0000 (18)
C250.029 (2)0.048 (3)0.0227 (17)0.0109 (19)−0.0007 (15)0.0078 (17)
C260.0230 (18)0.037 (2)0.0249 (17)0.0060 (16)0.0026 (15)0.0083 (16)
C270.0178 (16)0.027 (2)0.0159 (15)0.0016 (14)0.0007 (12)−0.0011 (13)
C280.0205 (17)0.037 (2)0.0214 (16)0.0066 (16)−0.0031 (13)0.0008 (15)
C290.0157 (16)0.035 (2)0.0158 (15)0.0065 (15)−0.0026 (12)0.0012 (14)
C300.0190 (17)0.040 (2)0.0136 (15)−0.0015 (16)−0.0068 (12)0.0006 (14)
C310.0198 (18)0.048 (3)0.0302 (19)−0.0002 (18)−0.0001 (15)0.0022 (18)
C320.0192 (19)0.063 (3)0.038 (2)−0.003 (2)−0.0019 (16)0.006 (2)
C330.033 (2)0.038 (2)0.0314 (19)−0.0047 (18)−0.0120 (17)0.0037 (17)
C340.029 (2)0.039 (2)0.0327 (19)−0.0004 (18)−0.0050 (16)−0.0026 (17)
C350.0239 (18)0.042 (2)0.0247 (17)−0.0024 (17)−0.0009 (15)−0.0066 (16)
C360.037 (2)0.032 (2)0.033 (2)0.0097 (18)−0.0045 (17)−0.0062 (17)
C370.0220 (17)0.031 (2)0.0191 (16)0.0053 (16)0.0009 (13)−0.0031 (14)
C380.0218 (17)0.029 (2)0.0189 (15)0.0064 (15)−0.0015 (13)−0.0012 (13)
C390.0200 (17)0.0264 (19)0.0188 (16)0.0042 (15)−0.0013 (13)−0.0009 (13)
C400.031 (2)0.023 (2)0.0244 (17)0.0002 (16)0.0031 (15)0.0008 (14)
C410.033 (2)0.0201 (19)0.0330 (19)−0.0019 (17)0.0091 (16)0.0033 (15)
C420.0247 (18)0.0208 (19)0.037 (2)0.0021 (16)−0.0025 (16)−0.0029 (16)
C430.0286 (19)0.029 (2)0.0259 (17)0.0031 (17)−0.0050 (15)−0.0051 (15)
C440.0171 (16)0.0237 (19)0.0170 (15)0.0033 (14)−0.0015 (12)−0.0037 (13)
C450.0202 (17)0.0240 (19)0.0159 (15)0.0000 (14)0.0020 (12)−0.0014 (13)
C460.0167 (16)0.0247 (19)0.0178 (15)0.0011 (14)0.0006 (12)0.0019 (13)
C470.0135 (16)0.034 (2)0.0197 (16)−0.0021 (14)0.0017 (12)0.0010 (14)
C480.0177 (16)0.028 (2)0.0232 (16)0.0009 (15)−0.0044 (13)0.0039 (14)
C490.0181 (16)0.0252 (19)0.0137 (14)0.0054 (14)0.0000 (12)−0.0016 (13)
C500.0146 (15)0.0266 (19)0.0167 (14)0.0004 (14)0.0022 (12)0.0029 (13)
C510.0211 (17)0.031 (2)0.0165 (15)−0.0021 (15)−0.0001 (13)0.0023 (13)
C520.0214 (18)0.039 (2)0.0206 (16)−0.0067 (17)−0.0070 (14)0.0004 (15)
C530.026 (2)0.052 (3)0.0238 (19)−0.0073 (19)−0.0087 (15)0.0017 (17)
C540.022 (2)0.073 (3)0.025 (2)0.007 (2)−0.0047 (15)0.010 (2)
C550.031 (2)0.043 (2)0.0209 (17)0.0121 (19)−0.0033 (15)0.0104 (16)
C560.030 (2)0.032 (2)0.0170 (15)0.0005 (17)0.0013 (14)0.0017 (15)
C570.0173 (16)0.0251 (19)0.0166 (14)0.0019 (14)0.0003 (12)0.0053 (13)
C580.0234 (18)0.030 (2)0.0298 (18)0.0012 (16)0.0015 (15)0.0001 (15)
C590.030 (2)0.037 (2)0.0279 (19)0.0077 (18)0.0057 (16)−0.0012 (16)
C600.025 (2)0.046 (3)0.035 (2)0.0063 (19)0.0117 (17)0.0111 (18)
C610.0231 (18)0.029 (2)0.040 (2)0.0047 (16)0.0063 (16)0.0135 (16)
C620.0210 (18)0.029 (2)0.0286 (18)0.0024 (15)0.0017 (14)0.0011 (15)
C630.0186 (16)0.034 (2)0.0202 (16)0.0032 (16)0.0011 (13)0.0059 (15)
C640.0190 (16)0.032 (2)0.0178 (15)−0.0026 (15)−0.0016 (13)0.0022 (14)
C650.0280 (19)0.034 (2)0.0270 (19)0.0040 (18)0.0046 (15)0.0083 (16)
C660.031 (2)0.042 (3)0.041 (2)0.006 (2)0.0082 (18)−0.0003 (19)
C670.028 (2)0.057 (3)0.0266 (19)−0.007 (2)0.0083 (16)0.0031 (19)
C680.031 (2)0.051 (3)0.0247 (18)−0.010 (2)0.0022 (16)0.0116 (18)
C690.0245 (18)0.032 (2)0.0222 (16)0.0009 (16)−0.0017 (13)0.0045 (14)
C700.0212 (17)0.026 (2)0.0163 (15)−0.0049 (15)0.0016 (13)−0.0016 (13)
C710.0172 (17)0.039 (2)0.0230 (16)−0.0067 (16)0.0022 (13)−0.0052 (15)
C720.0174 (16)0.033 (2)0.0145 (15)−0.0008 (15)−0.0004 (12)−0.0017 (13)
C730.0187 (17)0.033 (2)0.0194 (16)−0.0012 (16)0.0027 (13)−0.0001 (14)
C740.0215 (18)0.048 (3)0.0263 (18)−0.0052 (19)−0.0021 (15)0.0012 (17)
C750.0209 (19)0.050 (3)0.034 (2)0.0040 (18)−0.0005 (16)0.0011 (18)
C760.030 (2)0.040 (3)0.037 (2)0.0104 (19)0.0123 (17)0.0080 (18)
C770.031 (2)0.040 (2)0.034 (2)0.0011 (19)0.0073 (17)−0.0073 (17)
C780.0239 (18)0.043 (2)0.0248 (18)0.0043 (17)0.0000 (15)−0.0027 (16)
C790.040 (2)0.033 (2)0.027 (2)−0.0118 (19)0.0028 (17)−0.0044 (16)
C800.0229 (17)0.026 (2)0.0185 (15)−0.0044 (15)0.0000 (13)−0.0010 (13)
C810.0262 (18)0.0244 (19)0.0219 (16)−0.0047 (16)−0.0007 (14)−0.0022 (14)
C820.0255 (17)0.0189 (18)0.0172 (15)−0.0038 (15)0.0038 (13)0.0000 (12)
C830.0305 (19)0.026 (2)0.0189 (16)−0.0002 (16)−0.0004 (14)0.0023 (14)
C840.031 (2)0.032 (2)0.0259 (18)0.0022 (18)−0.0022 (15)0.0019 (15)
C850.030 (2)0.025 (2)0.036 (2)0.0067 (17)0.0040 (16)0.0011 (16)
C860.029 (2)0.026 (2)0.0257 (17)−0.0023 (16)0.0055 (15)−0.0010 (15)

Geometric parameters (Å, °)

Cl1—C91.737 (4)C32—H320.9500
Cl2—C131.739 (4)C33—C341.377 (6)
Cl3—C171.742 (4)C34—C351.390 (6)
Cl4—C331.740 (4)C34—H340.9500
Cl5—C521.749 (4)C35—H350.9500
Cl6—C561.752 (4)C36—H36A0.9800
Cl7—C601.744 (4)C36—H36B0.9800
Cl8—C761.742 (4)C36—H36C0.9800
N1—C71.289 (5)C38—C431.374 (5)
N1—O11.411 (3)C38—C391.404 (5)
N2—C41.467 (4)C39—C401.386 (5)
N2—C51.469 (4)C40—C411.399 (5)
N2—C201.474 (4)C40—H400.9500
N3—C281.455 (5)C41—C421.384 (6)
N3—C361.464 (5)C41—H410.9500
N3—C271.474 (4)C42—C431.391 (5)
N4—C371.354 (5)C42—H420.9500
N4—C381.396 (5)C43—H430.9500
N4—H40.87 (4)C44—C481.544 (5)
N5—C501.272 (4)C44—C451.560 (5)
N5—O41.396 (4)C44—C491.566 (4)
N6—C481.465 (4)C45—C461.529 (5)
N6—C471.465 (4)C46—C471.531 (5)
N6—C631.469 (4)C46—C721.573 (5)
N7—C711.451 (5)C46—C701.608 (5)
N7—C701.466 (4)C47—H47A0.9900
N7—C791.467 (5)C47—H47B0.9900
N8—C801.350 (5)C48—H48A0.9900
N8—C811.404 (5)C48—H48B0.9900
N8—H80.68 (5)C49—C571.512 (4)
O1—C11.474 (4)C49—C501.520 (4)
O2—C21.211 (4)C49—H491.0000
O3—C371.227 (4)C50—C511.484 (5)
O4—C441.471 (4)C51—C561.396 (5)
O5—C451.213 (4)C51—C521.403 (5)
O6—C801.224 (4)C52—C531.396 (5)
C1—C51.535 (4)C53—C541.390 (7)
C1—C61.552 (5)C53—H530.9500
C1—C21.560 (5)C54—C551.373 (7)
C2—C31.528 (4)C54—H540.9500
C3—C41.532 (5)C55—C561.381 (5)
C3—C291.569 (4)C55—H550.9500
C3—C271.601 (5)C57—C621.383 (5)
C4—H4A0.9900C57—C581.400 (5)
C4—H4B0.9900C58—C591.386 (5)
C5—H5A0.9900C58—H580.9500
C5—H5B0.9900C59—C601.376 (6)
C6—C141.511 (4)C59—H590.9500
C6—C71.520 (4)C60—C611.384 (6)
C6—H61.0000C61—C621.395 (5)
C7—C81.470 (5)C61—H610.9500
C8—C131.411 (5)C62—H620.9500
C8—C91.416 (5)C63—C641.520 (5)
C9—C101.387 (5)C63—H63A0.9900
C10—C111.374 (6)C63—H63B0.9900
C10—H100.9500C64—C691.390 (5)
C11—C121.381 (6)C64—C651.390 (5)
C11—H110.9500C65—C661.399 (5)
C12—C131.384 (5)C65—H650.9500
C12—H120.9500C66—C671.391 (6)
C14—C191.389 (5)C66—H660.9500
C14—C151.397 (5)C67—C681.380 (6)
C15—C161.407 (5)C67—H670.9500
C15—H150.9500C68—C691.383 (5)
C16—C171.358 (6)C68—H680.9500
C16—H160.9500C69—H690.9500
C17—C181.392 (6)C70—C821.517 (5)
C18—C191.388 (5)C70—C801.572 (4)
C18—H180.9500C71—C721.525 (5)
C19—H190.9500C71—H71A0.9900
C20—C211.518 (5)C71—H71B0.9900
C20—H20A0.9900C72—C731.513 (5)
C20—H20B0.9900C72—H721.0000
C21—C221.381 (6)C73—C781.390 (5)
C21—C261.397 (5)C73—C741.391 (5)
C22—C231.390 (5)C74—C751.391 (6)
C22—H220.9500C74—H740.9500
C23—C241.398 (6)C75—C761.365 (6)
C23—H230.9500C75—H750.9500
C24—C251.371 (6)C76—C771.387 (6)
C24—H240.9500C77—C781.383 (6)
C25—C261.386 (5)C77—H770.9500
C25—H250.9500C78—H780.9500
C26—H260.9500C79—H79A0.9800
C27—C391.520 (5)C79—H79B0.9800
C27—C371.570 (4)C79—H79C0.9800
C28—C291.523 (5)C81—C861.376 (5)
C28—H28A0.9900C81—C821.398 (5)
C28—H28B0.9900C82—C831.386 (5)
C29—C301.513 (5)C83—C841.386 (5)
C29—H291.0000C83—H830.9500
C30—C311.379 (5)C84—C851.400 (5)
C30—C351.397 (5)C84—H840.9500
C31—C321.393 (6)C85—C861.394 (5)
C31—H310.9500C85—H850.9500
C32—C331.378 (6)C86—H860.9500
C7—N1—O1109.3 (3)C39—C40—H40120.4
C4—N2—C5107.1 (3)C41—C40—H40120.4
C4—N2—C20111.1 (3)C42—C41—C40120.5 (4)
C5—N2—C20109.9 (3)C42—C41—H41119.7
C28—N3—C36114.7 (3)C40—C41—H41119.7
C28—N3—C27106.2 (3)C41—C42—C43121.1 (4)
C36—N3—C27116.1 (3)C41—C42—H42119.4
C37—N4—C38112.0 (3)C43—C42—H42119.4
C37—N4—H4122 (3)C38—C43—C42117.6 (3)
C38—N4—H4126 (3)C38—C43—H43121.2
C50—N5—O4110.2 (3)C42—C43—H43121.2
C48—N6—C47107.6 (3)O4—C44—C48105.8 (3)
C48—N6—C63110.4 (3)O4—C44—C45102.8 (3)
C47—N6—C63110.9 (3)C48—C44—C45115.6 (3)
C71—N7—C70106.9 (3)O4—C44—C49103.8 (2)
C71—N7—C79115.4 (3)C48—C44—C49117.4 (3)
C70—N7—C79114.7 (3)C45—C44—C49109.5 (3)
C80—N8—C81112.5 (3)O5—C45—C46122.2 (3)
C80—N8—H8124 (4)O5—C45—C44116.6 (3)
C81—N8—H8123 (4)C46—C45—C44121.2 (3)
N1—O1—C1110.2 (2)C45—C46—C47107.8 (3)
N5—O4—C44110.5 (2)C45—C46—C72110.7 (3)
O1—C1—C5105.8 (3)C47—C46—C72113.6 (3)
O1—C1—C6104.2 (2)C45—C46—C70109.2 (3)
C5—C1—C6117.8 (3)C47—C46—C70112.8 (3)
O1—C1—C2102.7 (2)C72—C46—C70102.6 (3)
C5—C1—C2115.5 (3)N6—C47—C46108.1 (3)
C6—C1—C2109.0 (3)N6—C47—H47A110.1
O2—C2—C3121.8 (3)C46—C47—H47A110.1
O2—C2—C1116.6 (3)N6—C47—H47B110.1
C3—C2—C1121.5 (3)C46—C47—H47B110.1
C2—C3—C4107.6 (3)H47A—C47—H47B108.4
C2—C3—C29111.4 (3)N6—C48—C44112.0 (3)
C4—C3—C29113.5 (3)N6—C48—H48A109.2
C2—C3—C27109.1 (3)C44—C48—H48A109.2
C4—C3—C27112.1 (3)N6—C48—H48B109.2
C29—C3—C27103.2 (3)C44—C48—H48B109.2
N2—C4—C3108.1 (3)H48A—C48—H48B107.9
N2—C4—H4A110.1C57—C49—C50113.1 (3)
C3—C4—H4A110.1C57—C49—C44117.1 (3)
N2—C4—H4B110.1C50—C49—C4499.9 (3)
C3—C4—H4B110.1C57—C49—H49108.7
H4A—C4—H4B108.4C50—C49—H49108.7
N2—C5—C1111.6 (3)C44—C49—H49108.7
N2—C5—H5A109.3N5—C50—C51121.4 (3)
C1—C5—H5A109.3N5—C50—C49114.7 (3)
N2—C5—H5B109.3C51—C50—C49123.4 (3)
C1—C5—H5B109.3C56—C51—C52115.0 (3)
H5A—C5—H5B108.0C56—C51—C50122.7 (3)
C14—C6—C7111.8 (3)C52—C51—C50122.2 (3)
C14—C6—C1116.9 (3)C53—C52—C51123.3 (4)
C7—C6—C1100.4 (3)C53—C52—Cl5115.5 (3)
C14—C6—H6109.1C51—C52—Cl5121.2 (3)
C7—C6—H6109.1C54—C53—C52117.8 (4)
C1—C6—H6109.1C54—C53—H53121.1
N1—C7—C8120.3 (3)C52—C53—H53121.1
N1—C7—C6114.5 (3)C55—C54—C53121.2 (4)
C8—C7—C6124.8 (3)C55—C54—H54119.4
C13—C8—C9115.3 (3)C53—C54—H54119.4
C13—C8—C7122.2 (3)C54—C55—C56119.0 (4)
C9—C8—C7122.3 (3)C54—C55—H55120.5
C10—C9—C8122.1 (4)C56—C55—H55120.5
C10—C9—Cl1116.4 (3)C55—C56—C51123.5 (4)
C8—C9—Cl1121.4 (3)C55—C56—Cl6117.5 (3)
C11—C10—C9119.6 (4)C51—C56—Cl6119.1 (3)
C11—C10—H10120.2C62—C57—C58119.2 (3)
C9—C10—H10120.2C62—C57—C49121.4 (3)
C10—C11—C12121.0 (4)C58—C57—C49119.3 (3)
C10—C11—H11119.5C59—C58—C57120.6 (4)
C12—C11—H11119.5C59—C58—H58119.7
C11—C12—C13119.0 (4)C57—C58—H58119.7
C11—C12—H12120.5C60—C59—C58119.0 (4)
C13—C12—H12120.5C60—C59—H59120.5
C12—C13—C8122.9 (3)C58—C59—H59120.5
C12—C13—Cl2117.2 (3)C59—C60—C61121.8 (4)
C8—C13—Cl2119.9 (3)C59—C60—Cl7119.2 (3)
C19—C14—C15119.2 (3)C61—C60—Cl7119.0 (3)
C19—C14—C6122.0 (3)C60—C61—C62118.7 (4)
C15—C14—C6118.8 (3)C60—C61—H61120.7
C14—C15—C16120.0 (4)C62—C61—H61120.7
C14—C15—H15120.0C57—C62—C61120.7 (4)
C16—C15—H15120.0C57—C62—H62119.6
C17—C16—C15119.0 (4)C61—C62—H62119.6
C17—C16—H16120.5N6—C63—C64114.8 (3)
C15—C16—H16120.5N6—C63—H63A108.6
C16—C17—C18122.4 (4)C64—C63—H63A108.6
C16—C17—Cl3118.6 (3)N6—C63—H63B108.6
C18—C17—Cl3119.0 (3)C64—C63—H63B108.6
C19—C18—C17118.3 (4)H63A—C63—H63B107.5
C19—C18—H18120.8C69—C64—C65118.5 (3)
C17—C18—H18120.8C69—C64—C63119.9 (3)
C18—C19—C14120.9 (4)C65—C64—C63121.3 (3)
C18—C19—H19119.5C64—C65—C66120.6 (4)
C14—C19—H19119.5C64—C65—H65119.7
N2—C20—C21114.6 (3)C66—C65—H65119.7
N2—C20—H20A108.6C67—C66—C65119.8 (4)
C21—C20—H20A108.6C67—C66—H66120.1
N2—C20—H20B108.6C65—C66—H66120.1
C21—C20—H20B108.6C68—C67—C66119.5 (4)
H20A—C20—H20B107.6C68—C67—H67120.2
C22—C21—C26118.6 (3)C66—C67—H67120.2
C22—C21—C20121.8 (3)C67—C68—C69120.5 (4)
C26—C21—C20119.4 (3)C67—C68—H68119.8
C21—C22—C23120.5 (4)C69—C68—H68119.8
C21—C22—H22119.7C68—C69—C64121.0 (4)
C23—C22—H22119.7C68—C69—H69119.5
C22—C23—C24120.4 (4)C64—C69—H69119.5
C22—C23—H23119.8N7—C70—C82109.7 (3)
C24—C23—H23119.8N7—C70—C80111.6 (3)
C25—C24—C23119.2 (4)C82—C70—C80100.9 (3)
C25—C24—H24120.4N7—C70—C46103.6 (3)
C23—C24—H24120.4C82—C70—C46120.0 (3)
C24—C25—C26120.4 (4)C80—C70—C46111.1 (3)
C24—C25—H25119.8N7—C71—C72101.7 (3)
C26—C25—H25119.8N7—C71—H71A111.4
C25—C26—C21120.9 (4)C72—C71—H71A111.4
C25—C26—H26119.5N7—C71—H71B111.4
C21—C26—H26119.5C72—C71—H71B111.4
N3—C27—C39109.0 (3)H71A—C71—H71B109.3
N3—C27—C37111.3 (3)C73—C72—C71116.0 (3)
C39—C27—C37100.7 (3)C73—C72—C46115.3 (3)
N3—C27—C3103.5 (3)C71—C72—C46103.6 (3)
C39—C27—C3120.1 (3)C73—C72—H72107.2
C37—C27—C3112.3 (3)C71—C72—H72107.2
N3—C28—C29102.0 (3)C46—C72—H72107.2
N3—C28—H28A111.4C78—C73—C74117.0 (4)
C29—C28—H28A111.4C78—C73—C72120.4 (3)
N3—C28—H28B111.4C74—C73—C72122.5 (4)
C29—C28—H28B111.4C73—C74—C75121.9 (4)
H28A—C28—H28B109.2C73—C74—H74119.1
C30—C29—C28116.5 (3)C75—C74—H74119.1
C30—C29—C3115.4 (3)C76—C75—C74119.1 (4)
C28—C29—C3103.4 (3)C76—C75—H75120.4
C30—C29—H29107.0C74—C75—H75120.4
C28—C29—H29107.0C75—C76—C77121.1 (4)
C3—C29—H29107.0C75—C76—Cl8119.9 (3)
C31—C30—C35117.9 (4)C77—C76—Cl8119.0 (4)
C31—C30—C29122.3 (4)C78—C77—C76118.8 (4)
C35—C30—C29119.7 (3)C78—C77—H77120.6
C30—C31—C32121.2 (4)C76—C77—H77120.6
C30—C31—H31119.4C77—C78—C73122.1 (4)
C32—C31—H31119.4C77—C78—H78119.0
C33—C32—C31119.7 (4)C73—C78—H78119.0
C33—C32—H32120.1N7—C79—H79A109.5
C31—C32—H32120.1N7—C79—H79B109.5
C34—C33—C32120.5 (4)H79A—C79—H79B109.5
C34—C33—Cl4119.6 (3)N7—C79—H79C109.5
C32—C33—Cl4119.9 (3)H79A—C79—H79C109.5
C33—C34—C35119.2 (4)H79B—C79—H79C109.5
C33—C34—H34120.4O6—C80—N8125.3 (3)
C35—C34—H34120.4O6—C80—C70126.5 (3)
C34—C35—C30121.4 (4)N8—C80—C70107.9 (3)
C34—C35—H35119.3C86—C81—C82122.9 (3)
C30—C35—H35119.3C86—C81—N8127.7 (3)
N3—C36—H36A109.5C82—C81—N8109.3 (3)
N3—C36—H36B109.5C83—C82—C81119.0 (3)
H36A—C36—H36B109.5C83—C82—C70130.8 (3)
N3—C36—H36C109.5C81—C82—C70109.4 (3)
H36A—C36—H36C109.5C84—C83—C82119.3 (3)
H36B—C36—H36C109.5C84—C83—H83120.4
O3—C37—N4125.1 (3)C82—C83—H83120.4
O3—C37—C27126.2 (3)C83—C84—C85120.6 (4)
N4—C37—C27108.4 (3)C83—C84—H84119.7
C43—C38—N4127.4 (3)C85—C84—H84119.7
C43—C38—C39122.7 (3)C86—C85—C84120.7 (4)
N4—C38—C39109.7 (3)C86—C85—H85119.6
C40—C39—C38118.7 (3)C84—C85—H85119.6
C40—C39—C27131.4 (3)C81—C86—C85117.4 (3)
C38—C39—C27109.1 (3)C81—C86—H86121.3
C39—C40—C41119.2 (3)C85—C86—H86121.3
C7—N1—O1—C1−8.1 (4)C41—C42—C43—C38−1.2 (6)
C50—N5—O4—C44−5.8 (4)N5—O4—C44—C48133.0 (3)
N1—O1—C1—C5136.3 (3)N5—O4—C44—C45−105.4 (3)
N1—O1—C1—C611.4 (3)N5—O4—C44—C498.7 (3)
N1—O1—C1—C2−102.2 (3)O4—C44—C45—O561.8 (4)
O1—C1—C2—O261.5 (4)C48—C44—C45—O5176.5 (3)
C5—C1—C2—O2176.1 (3)C49—C44—C45—O5−48.1 (4)
C6—C1—C2—O2−48.7 (4)O4—C44—C45—C46−115.2 (3)
O1—C1—C2—C3−115.6 (3)C48—C44—C45—C46−0.6 (5)
C5—C1—C2—C3−0.9 (5)C49—C44—C45—C46134.9 (3)
C6—C1—C2—C3134.3 (3)O5—C45—C46—C47−158.2 (3)
O2—C2—C3—C4−159.0 (3)C44—C45—C46—C4718.6 (4)
C1—C2—C3—C417.8 (4)O5—C45—C46—C72−33.4 (5)
O2—C2—C3—C29−34.1 (5)C44—C45—C46—C72143.5 (3)
C1—C2—C3—C29142.8 (3)O5—C45—C46—C7078.9 (4)
O2—C2—C3—C2779.2 (4)C44—C45—C46—C70−104.2 (3)
C1—C2—C3—C27−104.0 (3)C48—N6—C47—C4681.0 (3)
C5—N2—C4—C381.5 (3)C63—N6—C47—C46−158.1 (3)
C20—N2—C4—C3−158.5 (3)C45—C46—C47—N6−57.0 (3)
C2—C3—C4—N2−56.2 (3)C72—C46—C47—N6179.9 (3)
C29—C3—C4—N2−179.9 (3)C70—C46—C47—N663.7 (3)
C27—C3—C4—N263.7 (3)C47—N6—C48—C44−58.4 (4)
C4—N2—C5—C1−60.1 (4)C63—N6—C48—C44−179.5 (3)
C20—N2—C5—C1179.1 (3)O4—C44—C48—N6132.4 (3)
O1—C1—C5—N2133.9 (3)C45—C44—C48—N619.4 (4)
C6—C1—C5—N2−110.1 (3)C49—C44—C48—N6−112.4 (3)
C2—C1—C5—N221.0 (4)O4—C44—C49—C57114.6 (3)
O1—C1—C6—C14111.3 (3)C48—C44—C49—C57−1.7 (5)
C5—C1—C6—C14−5.5 (4)C45—C44—C49—C57−136.2 (3)
C2—C1—C6—C14−139.6 (3)O4—C44—C49—C50−7.8 (3)
O1—C1—C6—C7−9.8 (3)C48—C44—C49—C50−124.1 (3)
C5—C1—C6—C7−126.6 (3)C45—C44—C49—C50101.4 (3)
C2—C1—C6—C799.3 (3)O4—N5—C50—C51−173.0 (3)
O1—N1—C7—C8−172.0 (3)O4—N5—C50—C490.0 (4)
O1—N1—C7—C60.9 (4)C57—C49—C50—N5−120.1 (3)
C14—C6—C7—N1−118.8 (3)C44—C49—C50—N55.2 (4)
C1—C6—C7—N15.9 (4)C57—C49—C50—C5152.8 (4)
C14—C6—C7—C853.8 (5)C44—C49—C50—C51178.1 (3)
C1—C6—C7—C8178.5 (3)N5—C50—C51—C56−130.9 (4)
N1—C7—C8—C13−136.2 (4)C49—C50—C51—C5656.7 (5)
C6—C7—C8—C1351.6 (5)N5—C50—C51—C5252.5 (5)
N1—C7—C8—C949.1 (5)C49—C50—C51—C52−119.9 (4)
C6—C7—C8—C9−123.2 (4)C56—C51—C52—C53−3.1 (5)
C13—C8—C9—C10−2.8 (5)C50—C51—C52—C53173.8 (3)
C7—C8—C9—C10172.3 (3)C56—C51—C52—Cl5176.9 (3)
C13—C8—C9—Cl1179.5 (3)C50—C51—C52—Cl5−6.2 (5)
C7—C8—C9—Cl1−5.4 (5)C51—C52—C53—C54−0.5 (6)
C8—C9—C10—C113.3 (6)Cl5—C52—C53—C54179.5 (3)
Cl1—C9—C10—C11−178.9 (3)C52—C53—C54—C553.9 (6)
C9—C10—C11—C12−1.1 (6)C53—C54—C55—C56−3.4 (6)
C10—C11—C12—C13−1.4 (6)C54—C55—C56—C51−0.5 (6)
C11—C12—C13—C82.0 (5)C54—C55—C56—Cl6177.3 (3)
C11—C12—C13—Cl2−180.0 (3)C52—C51—C56—C553.6 (5)
C9—C8—C13—C120.1 (5)C50—C51—C56—C55−173.2 (3)
C7—C8—C13—C12−175.0 (3)C52—C51—C56—Cl6−174.2 (3)
C9—C8—C13—Cl2−177.9 (3)C50—C51—C56—Cl69.0 (5)
C7—C8—C13—Cl27.0 (5)C50—C49—C57—C6237.4 (4)
C7—C6—C14—C1938.1 (4)C44—C49—C57—C62−78.0 (4)
C1—C6—C14—C19−76.8 (4)C50—C49—C57—C58−146.2 (3)
C7—C6—C14—C15−143.4 (3)C44—C49—C57—C5898.4 (4)
C1—C6—C14—C15101.7 (4)C62—C57—C58—C592.5 (5)
C19—C14—C15—C163.3 (5)C49—C57—C58—C59−173.9 (3)
C6—C14—C15—C16−175.2 (3)C57—C58—C59—C60−0.9 (6)
C14—C15—C16—C17−1.3 (6)C58—C59—C60—C61−1.7 (6)
C15—C16—C17—C18−1.3 (7)C58—C59—C60—Cl7176.2 (3)
C15—C16—C17—Cl3177.0 (3)C59—C60—C61—C622.6 (6)
C16—C17—C18—C191.6 (7)Cl7—C60—C61—C62−175.4 (3)
Cl3—C17—C18—C19−176.6 (3)C58—C57—C62—C61−1.6 (5)
C17—C18—C19—C140.6 (6)C49—C57—C62—C61174.7 (3)
C15—C14—C19—C18−3.0 (5)C60—C61—C62—C57−0.9 (6)
C6—C14—C19—C18175.5 (3)C48—N6—C63—C64−69.4 (4)
C4—N2—C20—C21169.5 (3)C47—N6—C63—C64171.4 (3)
C5—N2—C20—C21−72.1 (4)N6—C63—C64—C69147.5 (3)
N2—C20—C21—C22−36.1 (5)N6—C63—C64—C65−38.7 (5)
N2—C20—C21—C26149.8 (3)C69—C64—C65—C660.7 (6)
C26—C21—C22—C231.6 (6)C63—C64—C65—C66−173.2 (4)
C20—C21—C22—C23−172.5 (4)C64—C65—C66—C670.6 (7)
C21—C22—C23—C240.0 (7)C65—C66—C67—C68−0.7 (7)
C22—C23—C24—C25−1.1 (7)C66—C67—C68—C69−0.7 (6)
C23—C24—C25—C260.6 (6)C67—C68—C69—C642.1 (6)
C24—C25—C26—C211.0 (6)C65—C64—C69—C68−2.1 (5)
C22—C21—C26—C25−2.1 (5)C63—C64—C69—C68172.0 (4)
C20—C21—C26—C25172.1 (3)C71—N7—C70—C82−163.8 (3)
C28—N3—C27—C39−163.8 (3)C79—N7—C70—C8266.9 (4)
C36—N3—C27—C3967.4 (4)C71—N7—C70—C8085.2 (3)
C28—N3—C27—C3786.0 (3)C79—N7—C70—C80−44.1 (4)
C36—N3—C27—C37−42.8 (4)C71—N7—C70—C46−34.5 (3)
C28—N3—C27—C3−34.8 (3)C79—N7—C70—C46−163.7 (3)
C36—N3—C27—C3−163.6 (3)C45—C46—C70—N7−109.9 (3)
C2—C3—C27—N3−110.2 (3)C47—C46—C70—N7130.3 (3)
C4—C3—C27—N3130.7 (3)C72—C46—C70—N77.6 (3)
C29—C3—C27—N38.3 (3)C45—C46—C70—C8212.9 (4)
C2—C3—C27—C3911.6 (4)C47—C46—C70—C82−107.0 (3)
C4—C3—C27—C39−107.5 (3)C72—C46—C70—C82130.4 (3)
C29—C3—C27—C39130.1 (3)C45—C46—C70—C80130.2 (3)
C2—C3—C27—C37129.7 (3)C47—C46—C70—C8010.3 (4)
C4—C3—C27—C3710.6 (4)C72—C46—C70—C80−112.3 (3)
C29—C3—C27—C37−111.8 (3)C70—N7—C71—C7247.9 (3)
C36—N3—C28—C29177.6 (3)C79—N7—C71—C72176.8 (3)
C27—N3—C28—C2948.0 (3)N7—C71—C72—C73−167.9 (3)
N3—C28—C29—C30−168.2 (3)N7—C71—C72—C46−40.6 (3)
N3—C28—C29—C3−40.4 (3)C45—C46—C72—C73−96.1 (3)
C2—C3—C29—C30−95.6 (3)C47—C46—C72—C7325.4 (4)
C4—C3—C29—C3026.0 (4)C70—C46—C72—C73147.5 (3)
C27—C3—C29—C30147.5 (3)C45—C46—C72—C71136.2 (3)
C2—C3—C29—C28136.0 (3)C47—C46—C72—C71−102.4 (3)
C4—C3—C29—C28−102.4 (3)C70—C46—C72—C7119.7 (3)
C27—C3—C29—C2819.1 (3)C71—C72—C73—C78−172.6 (3)
C28—C29—C30—C316.5 (5)C46—C72—C73—C7866.1 (4)
C3—C29—C30—C31−115.1 (4)C71—C72—C73—C747.7 (5)
C28—C29—C30—C35−172.0 (3)C46—C72—C73—C74−113.6 (4)
C3—C29—C30—C3566.4 (4)C78—C73—C74—C75−1.3 (6)
C35—C30—C31—C32−2.4 (6)C72—C73—C74—C75178.4 (4)
C29—C30—C31—C32179.1 (3)C73—C74—C75—C760.2 (6)
C30—C31—C32—C330.7 (6)C74—C75—C76—C770.8 (6)
C31—C32—C33—C340.5 (6)C74—C75—C76—Cl8−179.3 (3)
C31—C32—C33—Cl4−179.5 (3)C75—C76—C77—C78−0.6 (6)
C32—C33—C34—C350.1 (6)Cl8—C76—C77—C78179.5 (3)
Cl4—C33—C34—C35−179.9 (3)C76—C77—C78—C73−0.7 (6)
C33—C34—C35—C30−1.8 (6)C74—C73—C78—C771.6 (6)
C31—C30—C35—C343.0 (6)C72—C73—C78—C77−178.1 (3)
C29—C30—C35—C34−178.5 (3)C81—N8—C80—O6174.9 (4)
C38—N4—C37—O3175.4 (4)C81—N8—C80—C701.3 (4)
C38—N4—C37—C270.2 (4)N7—C70—C80—O6−59.4 (5)
N3—C27—C37—O3−60.6 (5)C82—C70—C80—O6−175.9 (4)
C39—C27—C37—O3−176.0 (4)C46—C70—C80—O655.7 (5)
C3—C27—C37—O354.9 (5)N7—C70—C80—N8114.2 (3)
N3—C27—C37—N4114.5 (3)C82—C70—C80—N8−2.3 (4)
C39—C27—C37—N4−0.9 (4)C46—C70—C80—N8−130.7 (3)
C3—C27—C37—N4−130.0 (3)C80—N8—C81—C86−174.9 (4)
C37—N4—C38—C43−175.1 (4)C80—N8—C81—C820.4 (5)
C37—N4—C38—C390.6 (4)C86—C81—C82—C833.4 (6)
C43—C38—C39—C404.1 (6)N8—C81—C82—C83−172.3 (3)
N4—C38—C39—C40−171.9 (3)C86—C81—C82—C70173.6 (3)
C43—C38—C39—C27174.7 (3)N8—C81—C82—C70−2.0 (4)
N4—C38—C39—C27−1.2 (4)N7—C70—C82—C8353.4 (5)
N3—C27—C39—C4053.2 (5)C80—C70—C82—C83171.3 (4)
C37—C27—C39—C40170.3 (4)C46—C70—C82—C83−66.3 (5)
C3—C27—C39—C40−65.9 (5)N7—C70—C82—C81−115.3 (3)
N3—C27—C39—C38−115.8 (3)C80—C70—C82—C812.6 (4)
C37—C27—C39—C381.3 (4)C46—C70—C82—C81125.0 (3)
C3—C27—C39—C38125.1 (3)C81—C82—C83—C84−3.7 (5)
C38—C39—C40—C41−3.8 (5)C70—C82—C83—C84−171.5 (4)
C27—C39—C40—C41−172.0 (4)C82—C83—C84—C851.1 (6)
C39—C40—C41—C421.3 (6)C83—C84—C85—C862.0 (6)
C40—C41—C42—C431.3 (6)C82—C81—C86—C85−0.3 (6)
N4—C38—C43—C42173.7 (4)N8—C81—C86—C85174.5 (4)
C39—C38—C43—C42−1.5 (6)C84—C85—C86—C81−2.4 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4···O6i0.87 (5)1.94 (5)2.804 (4)176 (4)
N8—H8···O3ii0.68 (5)2.14 (5)2.808 (4)173 (5)

Symmetry codes: (i) −x+3/2, y, z−1/2; (ii) −x+3/2, y, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2026).

References

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  • Kobayashi, J., Tsuda, M., Agemi, K., Shigemori, H., Ishibashi, M., Sasaki, T. & Mikamiy, Y. (1991). Tetrahedron, 47, 6617–6622.
  • Rigaku (2001). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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