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The title compound, C40H29Cl4N3O3.CHCl3, was synthesized by the intermolecular [3 + 2]-cyclo­addition of 2,6-di­chloro­benzo­nitrile oxide and 1-benzyl-3,5-di­benzyl­idene­piperidin-4-one. There are three rings linked by two spiro-C atoms. The piperidin-4-one ring adopts a chair conformation and the two five-membered isoxazoline rings are envelopes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009516/cv6189sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009516/cv6189Isup2.hkl
Contains datablock I

CCDC reference: 214824

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.064
  • wR factor = 0.196
  • Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.697 0.909 Tmin' and Tmax expected: 0.887 0.909 RR' = 0.786 Please check that your absorption correction is appropriate. PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Spiro-compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important process for the construction of spiro-compounds (Caramella & Grunanger., 1984). The structure of the title compound, (I), is reported here.

The molecular structure of (I) is illustrated in Fig. 1. (I) contains three spiro-linked rings, viz. a piperidin-4-one ring and two isoxazoline rings. The six-membered piperidin-4-one ring has the chair conformation. Attached to the isoxazoline rings are phenyl and 2,6-dichlorophenyl substituents.

The two isoxazoline rings (A and B) are non-planar, with envelope conformations. O2/N2/C7/C6 (ring A) and O3/N3/C9/C8 (ring B) form nearly planar arrangements, with mean derivations of 0.0088 and 0.0060 Å, respectively. The spiro-atom C2 lies 0.3436 (3) Å out from the plane of ring A and C5 is −0.3772 (3) Å out from the plane of ring B, forming the flaps of the envelopes. The dihedral angle between the C6/C2/O2 and O2/N2/C7/C6 mean planes is 21.9 (4)°. The same angle between the C8/C5/O3 and O3/N3/C9/C8 mean planes is 24.1 (4)°. The dihedral angle between the two substituted phenyl rings on ring A is 97.7 (3)°, while the same angle between the two substituted phenyl rings on ring B is 78.8 (3)°.

Experimental top

A mixture of 2,6-dichlorobenzonitrile oxide (3 mmol) and 1-benzyl-3,5-dibenzylidenepiperidin-4-one (1.5 mmol) in dry benzene (30 ml) was heated under reflux for 40 h. After evaporation of the solvent, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the title compound, (I). M.p. 442–443 K; IR (KBr): 1736 (CO), 1602, 1580 (CN, CC) cm−1; 1H NMR (CDCl3, p.p.m.): 2.42 (2H, d), 2.79 (2H, d), 3.10 (2H, m), 6.13 (2H, s), 6.94–7.37 (21H, m). 20 mg of (I) was dissolved in 15 ml chloroform, the solution was kept at room temperature for 10 d by natural evaporation to give colorless single crystals of (I) suitable for X-ray analysis.

Refinement top

H atoms were positioned geometrically and refined with riding-model constraints.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT and SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 30% probability level. H atoms and CHCl3 molecules have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the b axis, with CHCl3 molecules omitted.
13-Benzyl-3,10-bis-(2,6-dichloro-phenyl)-4,11-diphenyl −1,8-dioxa-2,9,13-triaza-dispiro[4.1.4.3] tetradeca-2,9-dien-6-one top
Crystal data top
C40H29Cl4N3O3·CHCl3Z = 2
Mr = 860.83F(000) = 880
Triclinic, P1Dx = 1.414 Mg m3
a = 11.905 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.046 (17) ÅCell parameters from 688 reflections
c = 15.17 (2) Åθ = 2.1–19.7°
α = 87.89 (3)°µ = 0.53 mm1
β = 81.20 (3)°T = 293 K
γ = 70.20 (3)°Plate, colorless
V = 2022 (5) Å30.22 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
7038 independent reflections
Radiation source: fine-focus sealed tube3463 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ϕ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1413
Tmin = 0.697, Tmax = 0.909k = 1410
10516 measured reflectionsl = 1816
Refinement top
Refinement on F278 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.064 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.196(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.35 e Å3
7038 reflectionsΔρmin = 0.31 e Å3
504 parameters
Crystal data top
C40H29Cl4N3O3·CHCl3γ = 70.20 (3)°
Mr = 860.83V = 2022 (5) Å3
Triclinic, P1Z = 2
a = 11.905 (18) ÅMo Kα radiation
b = 12.046 (17) ŵ = 0.53 mm1
c = 15.17 (2) ÅT = 293 K
α = 87.89 (3)°0.22 × 0.20 × 0.18 mm
β = 81.20 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7038 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
3463 reflections with I > 2σ(I)
Tmin = 0.697, Tmax = 0.909Rint = 0.039
10516 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06478 restraints
wR(F2) = 0.196H-atom parameters constrained
S = 1.07Δρmax = 0.35 e Å3
7038 reflectionsΔρmin = 0.31 e Å3
504 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl11.18974 (13)0.24329 (12)0.48262 (9)0.0670 (4)
Cl20.99328 (19)0.45635 (14)0.26948 (11)0.0965 (6)
Cl31.41005 (15)0.22579 (15)0.12547 (11)0.0862 (5)
Cl41.35066 (14)0.17778 (13)0.25401 (11)0.0800 (5)
O11.0840 (3)0.0054 (3)0.4048 (2)0.0516 (9)
O21.0159 (3)0.1084 (3)0.23324 (18)0.0434 (8)
O31.1101 (3)0.1922 (3)0.31799 (19)0.0456 (8)
N10.8665 (3)0.1345 (3)0.2263 (2)0.0436 (10)
N21.0754 (3)0.2248 (3)0.2582 (2)0.0444 (10)
N31.2365 (4)0.1483 (3)0.2918 (3)0.0483 (10)
C11.0391 (4)0.0257 (4)0.3380 (3)0.0369 (11)
C20.9537 (4)0.0377 (4)0.3142 (3)0.0366 (11)
C30.8374 (4)0.0546 (4)0.2933 (3)0.0449 (12)
H3A0.78750.01610.27110.054*
H3B0.79260.09870.34710.054*
C40.9309 (4)0.2034 (4)0.2596 (3)0.0432 (12)
H4A0.88650.24230.31550.052*
H4B0.93830.26350.21700.052*
C51.0559 (4)0.1219 (4)0.2741 (3)0.0383 (11)
C60.9397 (4)0.1284 (4)0.3841 (3)0.0380 (11)
H60.96250.11020.43990.046*
C71.0377 (4)0.2370 (4)0.3401 (3)0.0409 (11)
C81.1497 (4)0.0693 (4)0.1902 (3)0.0378 (11)
H81.15990.01420.18270.045*
C91.2585 (4)0.0804 (4)0.2236 (3)0.0415 (11)
C101.0853 (4)0.3521 (4)0.3835 (3)0.0470 (12)
C111.1506 (4)0.3619 (4)0.4538 (3)0.0519 (13)
C121.1937 (5)0.4649 (5)0.4990 (4)0.0681 (16)
H121.23600.46780.54630.082*
C131.1730 (5)0.5641 (5)0.4728 (5)0.0787 (19)
H131.20030.63420.50330.094*
C141.1124 (6)0.5597 (5)0.4021 (4)0.0758 (19)
H141.10090.62740.38380.091*
C151.0686 (5)0.4553 (4)0.3580 (3)0.0595 (14)
C160.8170 (4)0.1437 (4)0.4036 (3)0.0388 (11)
C170.7482 (4)0.1142 (4)0.4858 (3)0.0450 (12)
H170.77850.08670.53030.054*
C180.6351 (5)0.1243 (5)0.5041 (4)0.0636 (15)
H180.59030.10420.56050.076*
C190.5885 (5)0.1634 (5)0.4401 (5)0.0715 (17)
H190.51180.16930.45240.086*
C200.6557 (6)0.1942 (5)0.3566 (4)0.0719 (17)
H200.62440.22120.31260.086*
C210.7692 (5)0.1849 (5)0.3388 (3)0.0596 (14)
H210.81450.20650.28260.072*
C220.7601 (5)0.2097 (5)0.1872 (3)0.0615 (15)
H22A0.72020.15940.16670.074*
H22B0.78770.24840.13540.074*
C230.6691 (5)0.3024 (5)0.2497 (3)0.0565 (14)
C240.6760 (6)0.4151 (6)0.2546 (4)0.0802 (19)
H240.73680.43390.21770.096*
C250.5938 (7)0.4999 (7)0.3137 (6)0.105 (3)
H250.59990.57460.31620.126*
C260.5057 (9)0.4744 (9)0.3669 (6)0.127 (3)
H260.45120.53110.40690.153*
C270.4961 (7)0.3656 (9)0.3625 (6)0.130 (4)
H270.43360.34930.39910.156*
C280.5771 (6)0.2781 (6)0.3048 (5)0.087 (2)
H280.56940.20390.30340.104*
C291.3846 (4)0.0175 (4)0.1815 (3)0.0470 (12)
C301.4582 (5)0.0755 (5)0.1330 (3)0.0600 (15)
C311.5715 (5)0.0095 (7)0.0886 (4)0.0793 (19)
H311.62040.04770.05650.095*
C321.6117 (5)0.1115 (7)0.0917 (4)0.086 (2)
H321.68660.15440.06030.103*
C331.5426 (5)0.1702 (6)0.1408 (4)0.0723 (17)
H331.57030.25220.14310.087*
C341.4324 (5)0.1053 (5)0.1860 (3)0.0544 (13)
C351.1245 (4)0.1333 (4)0.1040 (3)0.0435 (12)
C361.1149 (4)0.2505 (5)0.0925 (3)0.0545 (13)
H361.12980.29180.13740.065*
C371.0834 (5)0.3058 (5)0.0151 (4)0.0721 (17)
H371.07600.38490.00820.086*
C381.0623 (5)0.2457 (7)0.0532 (4)0.081 (2)
H381.03990.28450.10520.098*
C391.0742 (5)0.1304 (7)0.0441 (3)0.080 (2)
H391.06190.08960.09050.096*
C401.1049 (4)0.0723 (5)0.0348 (3)0.0577 (14)
H401.11230.00680.04110.069*
C410.2860 (7)0.6084 (6)0.0946 (5)0.083 (2)0.810 (10)
H41A0.21380.66080.13150.100*0.810 (10)
Cl50.3587 (6)0.6925 (5)0.0280 (3)0.1390 (17)0.810 (10)
Cl60.2439 (4)0.5187 (3)0.0265 (3)0.1287 (14)0.810 (10)
Cl70.3856 (7)0.5236 (4)0.1627 (4)0.169 (2)0.810 (10)
C41'0.2557 (19)0.6032 (14)0.0890 (11)0.096 (5)*0.190 (10)
H41B0.16980.62550.11330.115*0.190 (10)
Cl5'0.2894 (15)0.7305 (9)0.0482 (8)0.091 (4)*0.190 (10)
Cl6'0.291 (2)0.4992 (15)0.0007 (12)0.151 (7)*0.190 (10)
Cl7'0.3440 (13)0.5394 (13)0.1737 (8)0.071 (4)*0.190 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0747 (10)0.0601 (9)0.0689 (9)0.0187 (7)0.0293 (7)0.0056 (7)
Cl20.1501 (17)0.0663 (10)0.0929 (12)0.0522 (11)0.0389 (11)0.0077 (9)
Cl30.0874 (12)0.0905 (12)0.0955 (12)0.0539 (10)0.0053 (9)0.0128 (9)
Cl40.0738 (10)0.0567 (9)0.0994 (12)0.0112 (8)0.0115 (9)0.0183 (8)
O10.070 (2)0.058 (2)0.0379 (18)0.0308 (18)0.0218 (17)0.0097 (16)
O20.062 (2)0.0414 (19)0.0292 (16)0.0206 (16)0.0076 (15)0.0017 (14)
O30.054 (2)0.0424 (19)0.0435 (18)0.0213 (16)0.0018 (16)0.0069 (15)
N10.047 (2)0.046 (2)0.039 (2)0.0149 (19)0.0137 (18)0.0102 (18)
N20.058 (3)0.036 (2)0.041 (2)0.019 (2)0.005 (2)0.0003 (18)
N30.054 (3)0.054 (3)0.043 (2)0.027 (2)0.007 (2)0.000 (2)
C10.040 (3)0.036 (3)0.032 (3)0.010 (2)0.003 (2)0.004 (2)
C20.050 (3)0.036 (3)0.026 (2)0.015 (2)0.007 (2)0.000 (2)
C30.048 (3)0.047 (3)0.043 (3)0.020 (2)0.013 (2)0.007 (2)
C40.052 (3)0.034 (3)0.040 (3)0.011 (2)0.004 (2)0.002 (2)
C50.045 (3)0.038 (3)0.035 (2)0.018 (2)0.005 (2)0.000 (2)
C60.048 (3)0.038 (3)0.030 (2)0.016 (2)0.010 (2)0.000 (2)
C70.051 (3)0.040 (3)0.037 (3)0.020 (2)0.011 (2)0.001 (2)
C80.043 (3)0.039 (3)0.034 (2)0.016 (2)0.008 (2)0.001 (2)
C90.048 (3)0.046 (3)0.035 (3)0.020 (2)0.011 (2)0.008 (2)
C100.048 (3)0.042 (3)0.043 (3)0.009 (2)0.004 (2)0.003 (2)
C110.047 (3)0.048 (3)0.053 (3)0.005 (2)0.010 (3)0.007 (3)
C120.060 (4)0.057 (4)0.070 (4)0.000 (3)0.008 (3)0.015 (3)
C130.070 (4)0.049 (4)0.093 (5)0.005 (3)0.003 (4)0.018 (3)
C140.083 (5)0.033 (3)0.098 (5)0.012 (3)0.012 (4)0.008 (3)
C150.070 (4)0.047 (3)0.059 (3)0.017 (3)0.004 (3)0.010 (3)
C160.049 (3)0.037 (3)0.034 (2)0.018 (2)0.012 (2)0.006 (2)
C170.048 (3)0.046 (3)0.042 (3)0.016 (2)0.009 (2)0.009 (2)
C180.049 (3)0.068 (4)0.070 (4)0.018 (3)0.001 (3)0.005 (3)
C190.051 (4)0.078 (4)0.094 (5)0.031 (3)0.018 (4)0.017 (4)
C200.084 (4)0.070 (4)0.085 (5)0.045 (4)0.040 (4)0.015 (3)
C210.072 (4)0.071 (4)0.049 (3)0.039 (3)0.015 (3)0.001 (3)
C220.071 (4)0.064 (4)0.054 (3)0.022 (3)0.025 (3)0.018 (3)
C230.044 (3)0.059 (4)0.060 (3)0.005 (3)0.022 (3)0.015 (3)
C240.063 (4)0.063 (4)0.104 (5)0.004 (3)0.022 (4)0.012 (4)
C250.082 (5)0.075 (5)0.139 (7)0.005 (5)0.030 (5)0.012 (5)
C260.101 (7)0.111 (8)0.125 (7)0.020 (6)0.007 (6)0.005 (6)
C270.070 (5)0.144 (8)0.126 (7)0.006 (6)0.025 (5)0.042 (7)
C280.056 (4)0.082 (5)0.108 (5)0.010 (4)0.005 (4)0.024 (4)
C290.042 (3)0.064 (4)0.039 (3)0.022 (3)0.008 (2)0.000 (2)
C300.053 (3)0.085 (4)0.049 (3)0.031 (3)0.011 (3)0.000 (3)
C310.052 (4)0.131 (6)0.062 (4)0.041 (4)0.004 (3)0.001 (4)
C320.045 (4)0.116 (6)0.079 (5)0.003 (4)0.005 (3)0.020 (4)
C330.048 (4)0.083 (4)0.076 (4)0.007 (3)0.013 (3)0.010 (4)
C340.048 (3)0.060 (4)0.054 (3)0.016 (3)0.008 (3)0.001 (3)
C350.037 (3)0.058 (3)0.034 (3)0.017 (2)0.001 (2)0.001 (2)
C360.058 (3)0.055 (3)0.052 (3)0.020 (3)0.010 (3)0.012 (3)
C370.058 (4)0.076 (4)0.071 (4)0.013 (3)0.007 (3)0.034 (4)
C380.059 (4)0.129 (6)0.061 (4)0.035 (4)0.026 (3)0.044 (4)
C390.067 (4)0.150 (7)0.038 (3)0.053 (4)0.019 (3)0.014 (4)
C400.053 (3)0.084 (4)0.046 (3)0.039 (3)0.000 (3)0.003 (3)
C410.079 (5)0.075 (4)0.090 (5)0.020 (4)0.008 (4)0.000 (4)
Cl50.171 (5)0.178 (4)0.103 (2)0.105 (4)0.027 (3)0.039 (2)
Cl60.109 (3)0.120 (2)0.166 (3)0.039 (2)0.036 (2)0.038 (2)
Cl70.229 (6)0.096 (2)0.171 (3)0.003 (3)0.120 (4)0.011 (2)
Geometric parameters (Å, º) top
Cl1—C111.735 (6)C19—C201.379 (8)
Cl2—C151.727 (6)C19—H190.9300
Cl3—C301.709 (6)C20—C211.379 (8)
Cl4—C341.725 (6)C20—H200.9300
O1—C11.196 (5)C21—H210.9300
O2—N21.407 (5)C22—C231.504 (7)
O2—C21.468 (5)C22—H22A0.9700
O3—N31.413 (5)C22—H22B0.9700
O3—C51.456 (5)C23—C281.380 (8)
N1—C41.453 (6)C23—C241.394 (8)
N1—C31.458 (5)C24—C251.387 (9)
N1—C221.480 (6)C24—H240.9300
N2—C71.276 (5)C25—C261.336 (11)
N3—C91.280 (6)C25—H250.9300
C1—C51.529 (6)C26—C271.359 (12)
C1—C21.550 (6)C26—H260.9300
C2—C31.523 (6)C27—C281.387 (10)
C2—C61.527 (6)C27—H270.9300
C3—H3A0.9700C28—H280.9300
C3—H3B0.9700C29—C341.397 (7)
C4—C51.523 (6)C29—C301.406 (7)
C4—H4A0.9700C30—C311.393 (8)
C4—H4B0.9700C31—C321.373 (9)
C5—C81.553 (6)C31—H310.9300
C6—C161.517 (6)C32—C331.377 (8)
C6—C71.520 (6)C32—H320.9300
C6—H60.9800C33—C341.368 (7)
C7—C101.480 (7)C33—H330.9300
C8—C91.508 (6)C35—C361.384 (7)
C8—C351.511 (6)C35—C401.395 (7)
C8—H80.9800C36—C371.367 (7)
C9—C291.486 (7)C36—H360.9300
C10—C111.392 (7)C37—C381.385 (9)
C10—C151.400 (7)C37—H370.9300
C11—C121.373 (7)C38—C391.351 (9)
C12—C131.384 (9)C38—H380.9300
C12—H120.9300C39—C401.397 (8)
C13—C141.370 (9)C39—H390.9300
C13—H130.9300C40—H400.9300
C14—C151.380 (8)C41—Cl71.730 (7)
C14—H140.9300C41—Cl51.746 (7)
C16—C171.369 (6)C41—Cl61.759 (7)
C16—C211.391 (6)C41—H41A0.9800
C17—C181.379 (7)C41'—Cl6'1.770 (11)
C17—H170.9300C41'—Cl7'1.772 (11)
C18—C191.358 (8)C41'—Cl5'1.779 (11)
C18—H180.9300C41'—H41B0.9800
N2—O2—C2108.6 (3)C18—C19—H19120.2
N3—O3—C5108.8 (3)C20—C19—H19120.2
C4—N1—C3112.0 (4)C19—C20—C21119.8 (5)
C4—N1—C22112.1 (4)C19—C20—H20120.1
C3—N1—C22112.9 (4)C21—C20—H20120.1
C7—N2—O2108.8 (3)C20—C21—C16120.9 (5)
C9—N3—O3107.8 (4)C20—C21—H21119.5
O1—C1—C5121.7 (4)C16—C21—H21119.5
O1—C1—C2122.2 (4)N1—C22—C23114.7 (4)
C5—C1—C2115.9 (4)N1—C22—H22A108.6
O2—C2—C3108.8 (3)C23—C22—H22A108.6
O2—C2—C6104.3 (3)N1—C22—H22B108.6
C3—C2—C6116.3 (4)C23—C22—H22B108.6
O2—C2—C1106.3 (3)H22A—C22—H22B107.6
C3—C2—C1109.0 (4)C28—C23—C24117.8 (6)
C6—C2—C1111.5 (4)C28—C23—C22121.1 (6)
N1—C3—C2109.4 (4)C24—C23—C22121.0 (5)
N1—C3—H3A109.8C25—C24—C23121.1 (7)
C2—C3—H3A109.8C25—C24—H24119.5
N1—C3—H3B109.8C23—C24—H24119.5
C2—C3—H3B109.8C26—C25—C24120.2 (8)
H3A—C3—H3B108.2C26—C25—H25119.9
N1—C4—C5109.3 (4)C24—C25—H25119.9
N1—C4—H4A109.8C25—C26—C27119.8 (9)
C5—C4—H4A109.8C25—C26—H26120.1
N1—C4—H4B109.8C27—C26—H26120.1
C5—C4—H4B109.8C26—C27—C28121.8 (8)
H4A—C4—H4B108.3C26—C27—H27119.1
O3—C5—C4106.9 (4)C28—C27—H27119.1
O3—C5—C1108.3 (3)C23—C28—C27119.3 (7)
C4—C5—C1107.6 (4)C23—C28—H28120.4
O3—C5—C8104.0 (3)C27—C28—H28120.4
C4—C5—C8117.8 (4)C34—C29—C30117.4 (5)
C1—C5—C8111.7 (4)C34—C29—C9119.6 (4)
C16—C6—C7112.8 (4)C30—C29—C9122.9 (5)
C16—C6—C2116.8 (4)C31—C30—C29119.6 (6)
C7—C6—C298.7 (3)C31—C30—Cl3119.2 (5)
C16—C6—H6109.3C29—C30—Cl3121.2 (4)
C7—C6—H6109.3C32—C31—C30120.6 (6)
C2—C6—H6109.3C32—C31—H31119.7
N2—C7—C10120.1 (4)C30—C31—H31119.7
N2—C7—C6114.6 (4)C31—C32—C33120.9 (6)
C10—C7—C6125.2 (4)C31—C32—H32119.5
C9—C8—C35113.1 (4)C33—C32—H32119.5
C9—C8—C597.5 (3)C34—C33—C32118.6 (6)
C35—C8—C5115.9 (4)C34—C33—H33120.7
C9—C8—H8109.9C32—C33—H33120.7
C35—C8—H8109.9C33—C34—C29122.8 (5)
C5—C8—H8109.9C33—C34—Cl4118.6 (5)
N3—C9—C29120.8 (4)C29—C34—Cl4118.5 (4)
N3—C9—C8115.9 (4)C36—C35—C40119.0 (5)
C29—C9—C8123.2 (4)C36—C35—C8122.9 (4)
C11—C10—C15116.4 (5)C40—C35—C8118.0 (5)
C11—C10—C7120.1 (4)C37—C36—C35120.1 (5)
C15—C10—C7123.5 (5)C37—C36—H36120.0
C12—C11—C10123.1 (5)C35—C36—H36120.0
C12—C11—Cl1117.0 (5)C36—C37—C38120.9 (6)
C10—C11—Cl1119.8 (4)C36—C37—H37119.5
C11—C12—C13118.5 (6)C38—C37—H37119.5
C11—C12—H12120.7C39—C38—C37119.9 (6)
C13—C12—H12120.7C39—C38—H38120.1
C14—C13—C12120.4 (5)C37—C38—H38120.1
C14—C13—H13119.8C38—C39—C40120.3 (6)
C12—C13—H13119.8C38—C39—H39119.9
C13—C14—C15120.3 (6)C40—C39—H39119.9
C13—C14—H14119.9C35—C40—C39119.8 (6)
C15—C14—H14119.9C35—C40—H40120.1
C14—C15—C10121.2 (5)C39—C40—H40120.1
C14—C15—Cl2117.7 (5)Cl7—C41—Cl5107.6 (4)
C10—C15—Cl2121.1 (4)Cl7—C41—Cl6111.0 (4)
C17—C16—C21117.8 (5)Cl5—C41—Cl6109.6 (4)
C17—C16—C6120.5 (4)Cl7—C41—H41A109.5
C21—C16—C6121.7 (4)Cl5—C41—H41A109.5
C16—C17—C18121.4 (5)Cl6—C41—H41A109.5
C16—C17—H17119.3Cl6'—C41'—Cl7'109.1 (9)
C18—C17—H17119.3Cl6'—C41'—Cl5'109.3 (9)
C19—C18—C17120.4 (5)Cl7'—C41'—Cl5'109.3 (8)
C19—C18—H18119.8Cl6'—C41'—H41B109.7
C17—C18—H18119.8Cl7'—C41'—H41B109.7
C18—C19—C20119.6 (6)Cl5'—C41'—H41B109.7
C2—O2—N2—C712.5 (5)Cl1—C11—C12—C13174.6 (4)
C5—O3—N3—C914.6 (4)C11—C12—C13—C141.1 (9)
N2—O2—C2—C3146.2 (3)C12—C13—C14—C151.8 (9)
N2—O2—C2—C621.4 (4)C13—C14—C15—C100.5 (9)
N2—O2—C2—C196.6 (4)C13—C14—C15—Cl2180.0 (5)
O1—C1—C2—O2114.9 (4)C11—C10—C15—C141.5 (7)
C5—C1—C2—O269.2 (4)C7—C10—C15—C14178.4 (5)
O1—C1—C2—C3128.0 (4)C11—C10—C15—Cl2178.0 (4)
C5—C1—C2—C348.0 (5)C7—C10—C15—Cl22.1 (7)
O1—C1—C2—C61.8 (6)C7—C6—C16—C17131.8 (4)
C5—C1—C2—C6177.8 (3)C2—C6—C16—C17114.8 (5)
C4—N1—C3—C265.3 (5)C7—C6—C16—C2149.7 (6)
C22—N1—C3—C2167.0 (4)C2—C6—C16—C2163.6 (6)
O2—C2—C3—N163.2 (4)C21—C16—C17—C180.3 (7)
C6—C2—C3—N1179.5 (3)C6—C16—C17—C18178.2 (4)
C1—C2—C3—N152.3 (5)C16—C17—C18—C190.4 (8)
C3—N1—C4—C567.9 (4)C17—C18—C19—C200.7 (8)
C22—N1—C4—C5164.0 (4)C18—C19—C20—C210.1 (9)
N3—O3—C5—C4149.1 (3)C19—C20—C21—C160.6 (8)
N3—O3—C5—C195.2 (4)C17—C16—C21—C200.8 (7)
N3—O3—C5—C823.8 (4)C6—C16—C21—C20177.6 (5)
N1—C4—C5—O3172.8 (3)C4—N1—C22—C2357.7 (6)
N1—C4—C5—C156.7 (4)C3—N1—C22—C2369.9 (6)
N1—C4—C5—C870.7 (5)N1—C22—C23—C2888.1 (6)
O1—C1—C5—O311.2 (6)N1—C22—C23—C2491.0 (6)
C2—C1—C5—O3164.8 (3)C28—C23—C24—C250.6 (9)
O1—C1—C5—C4126.4 (4)C22—C23—C24—C25178.5 (5)
C2—C1—C5—C449.6 (5)C23—C24—C25—C260.2 (11)
O1—C1—C5—C8102.8 (5)C24—C25—C26—C270.7 (14)
C2—C1—C5—C881.2 (5)C25—C26—C27—C281.2 (15)
O2—C2—C6—C16100.7 (4)C24—C23—C28—C270.1 (9)
C3—C2—C6—C1619.1 (5)C22—C23—C28—C27179.0 (6)
C1—C2—C6—C16145.0 (4)C26—C27—C28—C230.8 (12)
O2—C2—C6—C720.4 (4)N3—C9—C29—C34112.5 (5)
C3—C2—C6—C7140.2 (4)C8—C9—C29—C3467.4 (6)
C1—C2—C6—C793.9 (4)N3—C9—C29—C3070.4 (6)
O2—N2—C7—C10179.6 (4)C8—C9—C29—C30109.7 (5)
O2—N2—C7—C62.3 (5)C34—C29—C30—C313.0 (7)
C16—C6—C7—N2109.1 (4)C9—C29—C30—C31174.1 (5)
C2—C6—C7—N214.9 (5)C34—C29—C30—Cl3178.4 (4)
C16—C6—C7—C1068.1 (6)C9—C29—C30—Cl34.5 (7)
C2—C6—C7—C10167.9 (4)C29—C30—C31—C320.1 (8)
O3—C5—C8—C922.0 (4)Cl3—C30—C31—C32178.6 (5)
C4—C5—C8—C9140.0 (4)C30—C31—C32—C331.8 (10)
C1—C5—C8—C994.6 (4)C31—C32—C33—C340.4 (9)
O3—C5—C8—C3598.3 (4)C32—C33—C34—C292.9 (8)
C4—C5—C8—C3519.7 (6)C32—C33—C34—Cl4175.3 (5)
C1—C5—C8—C35145.1 (4)C30—C29—C34—C334.6 (8)
O3—N3—C9—C29178.3 (4)C9—C29—C34—C33172.6 (5)
O3—N3—C9—C81.6 (5)C30—C29—C34—Cl4173.6 (4)
C35—C8—C9—N3107.0 (5)C9—C29—C34—Cl49.1 (6)
C5—C8—C9—N315.4 (5)C9—C8—C35—C3651.9 (6)
C35—C8—C9—C2973.2 (6)C5—C8—C35—C3659.6 (6)
C5—C8—C9—C29164.5 (4)C9—C8—C35—C40131.1 (4)
N2—C7—C10—C11116.3 (5)C5—C8—C35—C40117.4 (5)
C6—C7—C10—C1166.6 (6)C40—C35—C36—C371.7 (7)
N2—C7—C10—C1563.8 (7)C8—C35—C36—C37175.3 (4)
C6—C7—C10—C15113.2 (5)C35—C36—C37—C380.9 (8)
C15—C10—C11—C122.2 (7)C36—C37—C38—C390.8 (9)
C7—C10—C11—C12177.7 (5)C37—C38—C39—C401.5 (9)
C15—C10—C11—Cl1173.2 (4)C36—C35—C40—C391.0 (7)
C7—C10—C11—Cl16.9 (6)C8—C35—C40—C39176.2 (4)
C10—C11—C12—C131.0 (8)C38—C39—C40—C350.7 (8)

Experimental details

Crystal data
Chemical formulaC40H29Cl4N3O3·CHCl3
Mr860.83
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.905 (18), 12.046 (17), 15.17 (2)
α, β, γ (°)87.89 (3), 81.20 (3), 70.20 (3)
V3)2022 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.53
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.697, 0.909
No. of measured, independent and
observed [I > 2σ(I)] reflections
10516, 7038, 3463
Rint0.039
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.196, 1.07
No. of reflections7038
No. of parameters504
No. of restraints78
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.31

Computer programs: SMART (Bruker, 1998), SMART, SAINT and SHELXTL (Bruker, 1998), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C11.196 (5)N1—C41.453 (6)
O2—N21.407 (5)N2—C71.276 (5)
O3—N31.413 (5)N3—C91.280 (6)
N2—O2—C2108.6 (3)C7—N2—O2108.8 (3)
N3—O3—C5108.8 (3)C9—N3—O3107.8 (4)
C4—N1—C3112.0 (4)
C2—O2—N2—C712.5 (5)O1—C1—C2—C61.8 (6)
C5—O3—N3—C914.6 (4)
 

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