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The title compound, C34H22Cl6N2O3·0.75H2O, was synthesized by the intermolecular [3+2]-cyclo­addition of 2,6-di­chloro­benzo­nitrile oxide and 2,6-bis(4-chloro­benzyl­idene)­cyclo­hexanone. There are three rings linked by two spiro-C atoms, with approximate C2 symmetry. The cyclo­hexane ring has a chair conformation and the two five-membered isoxazoline rings adopt envelope conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002034/cf6232sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002034/cf6232Isup2.hkl
Contains datablock I

CCDC reference: 204721

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • H-atom completeness 94%
  • Disorder in solvent or counterion
  • R factor = 0.068
  • wR factor = 0.186
  • Data-to-parameter ratio = 14.1

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: 0.770 0.918 Tmin' and Tmax expected: 0.877 0.918 RR' = 0.878 Please check that your absorption correction is appropriate. PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc. PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 32.00 A   3 General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C34 H23.5 Cl6 N2 O3.75 Atom count from the _atom_site data: C34 H22 Cl6 N2 O3.75 CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C34 H23.5 Cl6 N2 O3.75 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 68.00 68.00 0.00 H 47.00 44.00 3.00 Cl 12.00 12.00 0.00 N 4.00 4.00 0.00 O 7.50 7.50 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 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). They are found as pheromones, antibiotics, alkaloids (Gore et al., 1990), and antitumor agents (Tietze et al., 1998; Araki et al., 2002). 1,3-Dipolar cycloaddition reactions are considered the most important process for the construction of spiro-compounds containing five-membered rings, due to the high regio- and stereoselective properties of these reactions (Carmella & Grunanger, 1984).

The structure of the title compound, (I), is reported here. The molecular structure of (I) is illustrated in Fig. 1. Compound (I) contains three spiro-linked rings, viz. a cyclohexanone ring and two isoxazoline rings. The six-membered cyclohexanone ring has the usual chair conformation. The two isoxazoline rings are attached to this central ring through spiro-C atoms, giving approximate C2 symmetry. Attached to the isoxazoline rings are 4-chlorophenyl and 2,6-dichlorophenyl substituents.

The two isoxazoline rings (A and B) are non-planar, with envelope conformations. Rings O2/N1/C8/C7 (ring A) and O3/N2/C10/C9 (ring B) form almost exactly planar arrangements; the torsion angles O2—-N1—-C8—-C7 of −0.9 (5)° and O3—N2—C10—C9 of 1.9 (5)° are similar to that of 1.4 (3)° in a related structure (Feng et al., 1997). The spiro-atom C2 lies 0.190 (3) Å from the O2/N1/C8/C7 plane in ring A and atom C6 is 0.419 (3) Å from the O3/N2/C10/C9 plane in ring B, these two atoms forming the flaps of the envelopes. The dihedral angle between the C7/C2/O2 plane and the C7/C8/N1/O2 mean plane is 12.0 (4)°, and that between the C9/C6/O3 plane and the C9/C10/N2/O3 mean plane is 26.7 (4)°. The bond lengths O2—N1 and O3—N2 are 1.427 (5) and 1.416 (5) Å, respectively, and are comparable to that of 1.413 (2) Å in the related structure (Feng et al., 1997).

The dihedral angle between the two substituted phenyl rings on ring A is 95.5 (2)°, while that between the two subsituted phenyl rings on ring B is 91.2 (2)°; in each case, the 2,6-dichlorophenyl ring is oriented approximately perpendicular to the 4-chlorophenyl ring. The dihedral angle between the planar part (O2/N1/C8/C7) of ring A and its 4-chlorophenyl substituent ring is 88.2 (3)° and that between the planar part of ring B and its 4-chlorophenyl substituent ring is 89.2 (3)°. The dihedral angle between the two isoxazoline ring envelope flaps (C7/C2/O2 and C9/C6/O3), which form the spiro linkages with the central ring, is 66.2 (3)°.

The Cl—C bond lengths are in the range 1.732 (6)–1.746 (7) Å, in agreement with values reported in the literature (Busetti et al., 1980; Sutherland & Ali-Adib, 1987).

Experimental top

A mixture of 2,6-dichlorobenzonitrile oxide (3 mmol) and 2,6-bis(4-chlorobenzylidene)cyclohexanone (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. 498–499 K; IR (KBr): 1736 (CO), 1602, 1580 (CN, CC) cm−1; 1H NMR (CDCl3, p.p.m.): 1.57 (4H, m), 1.94 (2H, m), 6.18 (2H, s), 7.13–7.34 (14H, m); 13C NMR (CDCl3, p.p.m.): 17.71, 30.78, 57.39, 94.87, 126.71, 128.71, 130.08, 131.11, 132.34, 132.67, 134.54, 135.32, 135.97, 136.74, 156.36, 198.62, 206.84. 20 mg of (I) was dissolved in 15 ml chloroform, and the solution was kept at room temperature for 10 d, to give colorless single crystals of (I) by evaporation.

Refinement top

H atoms were positioned geometrically and refined with riding-model constraints. Residual electron-density features were interpreted as water molecules, disordered over three partially occupied sites, one of them on an inversion centre and the other two related by it. Occupancies of 0.5 were assigned on the basis of reasonable refined displacement parameters, corresponding to 0.75 molecules of water in the asymmetric unit. H atoms were not included for these water molecules, which are presumed to derive from the undried chloroform solvent used for recrystallization.

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), drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the a axis, without the disordered water molecules.
4,11-Bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa- 2,9-diaza-dispiro[4.1.4.3]tetradeca-2,9-dien-6-one hydrate top
Crystal data top
C34H22Cl6N2O3·0.75H2OF(000) = 744
Mr = 732.75Dx = 1.402 Mg m3
Triclinic, P1Melting point = 498–499 K
a = 8.834 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.304 (3) ÅCell parameters from 747 reflections
c = 20.576 (6) Åθ = 2.8–21.4°
α = 91.915 (7)°µ = 0.53 mm1
β = 96.371 (7)°T = 293 K
γ = 110.718 (10)°Plate, colorless
V = 1735.7 (10) Å30.24 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
5928 independent reflections
Radiation source: fine-focus sealed tube3052 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 25.0°, θmin = 4.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1010
Tmin = 0.770, Tmax = 0.918k = 1212
8673 measured reflectionsl = 1224
Refinement top
Refinement on F249 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.186(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.51 e Å3
5928 reflectionsΔρmin = 0.42 e Å3
421 parameters
Crystal data top
C34H22Cl6N2O3·0.75H2Oγ = 110.718 (10)°
Mr = 732.75V = 1735.7 (10) Å3
Triclinic, P1Z = 2
a = 8.834 (3) ÅMo Kα radiation
b = 10.304 (3) ŵ = 0.53 mm1
c = 20.576 (6) ÅT = 293 K
α = 91.915 (7)°0.24 × 0.20 × 0.16 mm
β = 96.371 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5928 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
3052 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 0.918Rint = 0.034
8673 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06849 restraints
wR(F2) = 0.186H-atom parameters constrained
S = 1.02Δρmax = 0.51 e Å3
5928 reflectionsΔρmin = 0.42 e Å3
421 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)
N10.5047 (5)0.8085 (4)0.76958 (19)0.0484 (10)
N21.0439 (5)0.9456 (5)0.6326 (2)0.0570 (11)
O10.9024 (4)1.0924 (4)0.73460 (18)0.0782 (12)
O20.5206 (4)0.8588 (3)0.70596 (14)0.0479 (8)
O30.9730 (4)1.0462 (3)0.61719 (16)0.0589 (9)
Cl10.2735 (4)1.4464 (3)0.83911 (13)0.1747 (14)
Cl20.22170 (18)0.78122 (18)0.86357 (8)0.0874 (5)
Cl30.8832 (2)0.9862 (3)0.89438 (8)0.1097 (7)
Cl40.4646 (2)0.56384 (14)0.34339 (7)0.0739 (5)
Cl50.8455 (2)0.71902 (19)0.76222 (7)0.0802 (5)
Cl61.1063 (2)0.70888 (19)0.53636 (8)0.0874 (6)
C10.7853 (6)1.0321 (5)0.6963 (2)0.0435 (11)
C20.6110 (6)1.0077 (5)0.7126 (2)0.0428 (11)
C30.5278 (7)1.0741 (6)0.6621 (2)0.0572 (14)
H3A0.57951.17450.66860.069*
H3B0.41411.04940.66840.069*
C40.5379 (7)1.0264 (5)0.5922 (2)0.0579 (14)
H4A0.47900.92680.58470.070*
H4B0.48561.07190.56150.070*
C50.7130 (7)1.0592 (5)0.5792 (2)0.0541 (14)
H5A0.77041.15920.58440.065*
H5B0.71341.02760.53440.065*
C60.8024 (6)0.9899 (5)0.6258 (2)0.0460 (12)
C70.6171 (6)1.0520 (5)0.7857 (2)0.0438 (11)
H70.73181.09860.80430.053*
C80.5550 (5)0.9117 (5)0.8119 (2)0.0460 (12)
C90.7595 (5)0.8307 (4)0.6148 (2)0.0397 (11)
H90.68810.78210.64650.048*
C100.9304 (6)0.8285 (5)0.6328 (2)0.0440 (11)
C110.5247 (6)1.1469 (5)0.8009 (2)0.0472 (12)
C120.3574 (7)1.1040 (6)0.7914 (3)0.0649 (15)
H120.29521.01220.77660.078*
C130.2806 (9)1.1978 (9)0.8039 (3)0.090 (2)
H130.16731.16920.79790.108*
C140.3738 (14)1.3314 (9)0.8249 (3)0.089 (2)
C150.5378 (14)1.3750 (7)0.8345 (3)0.096 (2)
H150.59901.46700.84920.115*
C160.6145 (8)1.2839 (6)0.8228 (3)0.0677 (16)
H160.72791.31430.82950.081*
C170.5526 (6)0.8856 (5)0.8832 (2)0.0514 (13)
C180.4108 (7)0.8282 (5)0.9115 (3)0.0611 (14)
C190.4134 (9)0.8064 (6)0.9775 (3)0.0787 (18)
H190.31620.76520.99480.094*
C200.5575 (11)0.8452 (8)1.0166 (3)0.089 (2)
H200.55890.83181.06110.107*
C210.7001 (9)0.9034 (7)0.9918 (3)0.0829 (19)
H210.79910.93061.01910.100*
C220.6970 (7)0.9220 (6)0.9255 (3)0.0699 (16)
C230.6846 (5)0.7683 (4)0.5453 (2)0.0393 (11)
C240.5204 (5)0.6848 (4)0.5330 (2)0.0428 (11)
H240.45680.66900.56710.051*
C250.4508 (6)0.6251 (5)0.4708 (2)0.0473 (12)
H250.34040.57060.46260.057*
C260.5484 (6)0.6477 (5)0.4206 (2)0.0450 (12)
C270.7065 (6)0.7348 (5)0.4310 (2)0.0473 (12)
H270.76840.75410.39640.057*
C280.7745 (5)0.7943 (5)0.4931 (2)0.0439 (11)
H280.88340.85330.50030.053*
C290.9711 (5)0.7045 (5)0.6495 (2)0.0475 (12)
C300.9347 (6)0.6451 (6)0.7082 (3)0.0595 (14)
C310.9686 (8)0.5288 (7)0.7260 (3)0.0797 (18)
H310.94190.49090.76540.096*
C321.0431 (9)0.4700 (7)0.6840 (4)0.089 (2)
H321.06680.39210.69540.106*
C331.0817 (8)0.5250 (7)0.6265 (3)0.0790 (18)
H331.13060.48440.59830.095*
C341.0480 (6)0.6413 (6)0.6100 (3)0.0583 (14)
O41.00000.50001.00000.256 (14)0.50
O4'1.119 (3)0.382 (2)1.0168 (11)0.237 (8)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.044 (2)0.053 (3)0.047 (3)0.017 (2)0.002 (2)0.003 (2)
N20.050 (3)0.062 (3)0.054 (3)0.013 (2)0.009 (2)0.004 (2)
O10.047 (2)0.111 (3)0.053 (2)0.005 (2)0.0019 (19)0.020 (2)
O20.0418 (18)0.055 (2)0.0365 (18)0.0072 (15)0.0024 (15)0.0041 (15)
O30.057 (2)0.049 (2)0.063 (2)0.0053 (18)0.0207 (18)0.0079 (17)
Cl10.286 (4)0.197 (3)0.1229 (19)0.203 (3)0.017 (2)0.0159 (17)
Cl20.0620 (9)0.1000 (13)0.0880 (12)0.0123 (9)0.0142 (9)0.0137 (9)
Cl30.0594 (10)0.201 (2)0.0660 (10)0.0458 (12)0.0060 (8)0.0267 (12)
Cl40.0966 (11)0.0592 (9)0.0491 (8)0.0162 (8)0.0177 (8)0.0041 (6)
Cl50.0926 (11)0.1196 (13)0.0472 (8)0.0571 (10)0.0177 (8)0.0247 (8)
Cl60.0959 (12)0.1228 (14)0.0736 (10)0.0655 (11)0.0402 (9)0.0318 (9)
C10.048 (3)0.040 (3)0.033 (3)0.006 (2)0.005 (2)0.002 (2)
C20.049 (3)0.043 (3)0.034 (3)0.016 (2)0.005 (2)0.001 (2)
C30.076 (4)0.072 (4)0.034 (3)0.045 (3)0.007 (3)0.000 (2)
C40.088 (4)0.056 (3)0.039 (3)0.042 (3)0.011 (3)0.002 (2)
C50.091 (4)0.038 (3)0.034 (3)0.025 (3)0.004 (3)0.006 (2)
C60.048 (3)0.041 (3)0.042 (3)0.007 (2)0.007 (2)0.006 (2)
C70.043 (3)0.050 (3)0.035 (3)0.016 (2)0.006 (2)0.001 (2)
C80.038 (3)0.052 (3)0.045 (3)0.015 (2)0.001 (2)0.001 (2)
C90.036 (2)0.041 (3)0.037 (3)0.007 (2)0.005 (2)0.008 (2)
C100.043 (3)0.048 (3)0.037 (3)0.010 (2)0.010 (2)0.007 (2)
C110.065 (3)0.051 (3)0.026 (2)0.025 (3)0.001 (2)0.001 (2)
C120.062 (4)0.073 (4)0.061 (4)0.031 (3)0.012 (3)0.003 (3)
C130.091 (5)0.131 (7)0.070 (4)0.074 (5)0.011 (4)0.004 (4)
C140.148 (7)0.083 (5)0.058 (4)0.072 (6)0.003 (5)0.001 (4)
C150.170 (9)0.059 (4)0.060 (4)0.043 (5)0.014 (5)0.001 (3)
C160.090 (4)0.055 (4)0.053 (3)0.019 (3)0.012 (3)0.001 (3)
C170.060 (3)0.057 (3)0.042 (3)0.029 (3)0.002 (3)0.007 (2)
C180.076 (4)0.056 (3)0.055 (3)0.026 (3)0.014 (3)0.012 (3)
C190.105 (5)0.079 (4)0.062 (4)0.038 (4)0.030 (4)0.029 (3)
C200.126 (6)0.114 (6)0.047 (4)0.067 (5)0.010 (4)0.022 (4)
C210.091 (5)0.119 (6)0.048 (4)0.051 (4)0.002 (4)0.020 (4)
C220.084 (4)0.094 (4)0.042 (3)0.046 (4)0.001 (3)0.014 (3)
C230.042 (3)0.038 (3)0.040 (3)0.016 (2)0.005 (2)0.007 (2)
C240.038 (3)0.038 (3)0.051 (3)0.012 (2)0.006 (2)0.008 (2)
C250.038 (3)0.035 (3)0.062 (3)0.010 (2)0.011 (3)0.000 (2)
C260.059 (3)0.036 (3)0.039 (3)0.018 (2)0.003 (2)0.006 (2)
C270.054 (3)0.042 (3)0.043 (3)0.014 (2)0.008 (2)0.002 (2)
C280.034 (2)0.049 (3)0.045 (3)0.009 (2)0.007 (2)0.008 (2)
C290.031 (2)0.062 (3)0.043 (3)0.011 (2)0.003 (2)0.004 (2)
C300.049 (3)0.083 (4)0.050 (3)0.028 (3)0.003 (3)0.015 (3)
C310.085 (4)0.100 (5)0.071 (4)0.049 (4)0.018 (4)0.038 (4)
C320.100 (5)0.091 (5)0.093 (5)0.057 (4)0.005 (4)0.028 (4)
C330.083 (4)0.097 (5)0.078 (4)0.057 (4)0.010 (4)0.018 (4)
C340.052 (3)0.077 (4)0.051 (3)0.030 (3)0.004 (3)0.009 (3)
O40.20 (2)0.21 (2)0.41 (4)0.059 (15)0.25 (3)0.15 (2)
O4'0.28 (2)0.188 (16)0.236 (19)0.074 (14)0.050 (16)0.032 (13)
Geometric parameters (Å, º) top
N1—C81.267 (6)C12—C131.396 (8)
N1—O21.427 (5)C12—H120.930
N2—C101.267 (6)C13—C141.356 (10)
N2—O31.416 (5)C13—H130.930
O1—C11.187 (5)C14—C151.346 (11)
O2—C21.450 (5)C15—C161.368 (9)
O3—C61.445 (6)C15—H150.930
Cl1—C141.746 (7)C16—H160.930
Cl2—C181.740 (6)C17—C221.386 (7)
Cl3—C221.745 (7)C17—C181.385 (7)
Cl4—C261.735 (5)C18—C191.382 (8)
Cl5—C301.732 (6)C19—C201.349 (9)
Cl6—C341.743 (6)C19—H190.930
C1—C61.539 (6)C20—C211.355 (9)
C1—C21.547 (7)C20—H200.930
C2—C31.524 (6)C21—C221.382 (8)
C2—C71.546 (6)C21—H210.930
C3—C41.527 (6)C23—C281.382 (6)
C3—H3A0.970C23—C241.389 (6)
C3—H3B0.970C24—C251.378 (6)
C4—C51.518 (8)C24—H240.930
C4—H4A0.970C25—C261.392 (7)
C4—H4B0.970C25—H250.930
C5—C61.526 (6)C26—C271.355 (7)
C5—H5A0.970C27—C281.375 (6)
C5—H5B0.970C27—H270.930
C6—C91.550 (6)C28—H280.930
C7—C81.497 (7)C29—C301.390 (7)
C7—C111.523 (6)C29—C341.395 (7)
C7—H70.980C30—C311.385 (8)
C8—C171.501 (7)C31—C321.386 (9)
C9—C101.522 (6)C31—H310.930
C9—C231.526 (6)C32—C331.355 (9)
C9—H90.980C32—H320.930
C10—C291.485 (7)C33—C341.377 (8)
C11—C121.373 (7)C33—H330.930
C11—C161.382 (7)
C8—N1—O2108.7 (4)C15—C14—C13121.6 (7)
C10—N2—O3108.6 (4)C15—C14—Cl1120.7 (7)
N1—O2—C2109.3 (3)C13—C14—Cl1117.7 (8)
N2—O3—C6108.8 (3)C14—C15—C16120.0 (7)
O1—C1—C6120.8 (4)C14—C15—H15120.0
O1—C1—C2121.5 (4)C16—C15—H15120.0
C6—C1—C2117.3 (4)C15—C16—C11120.5 (7)
O2—C2—C3107.9 (4)C15—C16—H16119.8
O2—C2—C7105.0 (3)C11—C16—H16119.8
C3—C2—C7117.1 (4)C22—C17—C18115.7 (5)
O2—C2—C1107.8 (3)C22—C17—C8120.6 (5)
C3—C2—C1108.6 (4)C18—C17—C8123.7 (5)
C7—C2—C1110.1 (4)C19—C18—C17122.1 (6)
C2—C3—C4111.5 (4)C19—C18—Cl2118.0 (5)
C2—C3—H3A109.3C17—C18—Cl2119.9 (4)
C4—C3—H3A109.3C20—C19—C18119.7 (7)
C2—C3—H3B109.3C20—C19—H19120.1
C4—C3—H3B109.3C18—C19—H19120.1
H3A—C3—H3B108.0C19—C20—C21120.8 (6)
C5—C4—C3112.1 (4)C19—C20—H20119.6
C5—C4—H4A109.2C21—C20—H20119.6
C3—C4—H4A109.2C20—C21—C22119.3 (6)
C5—C4—H4B109.2C20—C21—H21120.4
C3—C4—H4B109.2C22—C21—H21120.4
H4A—C4—H4B107.9C21—C22—C17122.4 (6)
C4—C5—C6111.8 (4)C21—C22—Cl3118.0 (5)
C4—C5—H5A109.2C17—C22—Cl3119.5 (4)
C6—C5—H5A109.2C28—C23—C24118.3 (4)
C4—C5—H5B109.2C28—C23—C9122.0 (4)
C6—C5—H5B109.2C24—C23—C9119.6 (4)
H5A—C5—H5B107.9C25—C24—C23120.7 (4)
O3—C6—C5107.3 (4)C25—C24—H24119.7
O3—C6—C1108.5 (4)C23—C24—H24119.7
C5—C6—C1107.6 (4)C24—C25—C26119.0 (4)
O3—C6—C9103.0 (4)C24—C25—H25120.5
C5—C6—C9118.4 (4)C26—C25—H25120.5
C1—C6—C9111.5 (4)C27—C26—C25121.0 (4)
C8—C7—C11114.8 (4)C27—C26—Cl4119.8 (4)
C8—C7—C299.7 (4)C25—C26—Cl4119.2 (4)
C11—C7—C2117.0 (4)C26—C27—C28119.4 (4)
C8—C7—H7108.3C26—C27—H27120.3
C11—C7—H7108.3C28—C27—H27120.3
C2—C7—H7108.3C27—C28—C23121.4 (4)
N1—C8—C7115.9 (4)C27—C28—H28119.3
N1—C8—C17118.9 (4)C23—C28—H28119.3
C7—C8—C17125.2 (4)C30—C29—C34115.6 (5)
C10—C9—C23112.8 (4)C30—C29—C10120.1 (5)
C10—C9—C698.0 (3)C34—C29—C10124.3 (4)
C23—C9—C6115.0 (4)C31—C30—C29122.6 (5)
C10—C9—H9110.2C31—C30—Cl5118.0 (4)
C23—C9—H9110.2C29—C30—Cl5119.4 (4)
C6—C9—H9110.2C30—C31—C32118.8 (6)
N2—C10—C29119.8 (4)C30—C31—H31120.6
N2—C10—C9114.3 (4)C32—C31—H31120.6
C29—C10—C9126.0 (4)C33—C32—C31120.6 (6)
C12—C11—C16118.8 (5)C33—C32—H32119.7
C12—C11—C7123.1 (5)C31—C32—H32119.7
C16—C11—C7118.0 (5)C32—C33—C34119.6 (6)
C11—C12—C13120.1 (6)C32—C33—H33120.2
C11—C12—H12119.9C34—C33—H33120.2
C13—C12—H12119.9C33—C34—C29122.8 (5)
C14—C13—C12118.9 (7)C33—C34—Cl6116.9 (4)
C14—C13—H13120.5C29—C34—Cl6120.2 (4)
C12—C13—H13120.5
C8—N1—O2—C28.7 (5)C11—C12—C13—C140.6 (9)
C10—N2—O3—C616.3 (5)C12—C13—C14—C150.6 (11)
N1—O2—C2—C3137.9 (3)C12—C13—C14—Cl1179.2 (5)
N1—O2—C2—C712.3 (4)C13—C14—C15—C160.3 (11)
N1—O2—C2—C1105.0 (4)Cl1—C14—C15—C16179.5 (4)
O1—C1—C2—O2122.3 (5)C14—C15—C16—C110.1 (10)
C6—C1—C2—O264.4 (5)C12—C11—C16—C150.2 (8)
O1—C1—C2—C3121.1 (5)C7—C11—C16—C15177.2 (5)
C6—C1—C2—C352.2 (5)N1—C8—C17—C22114.4 (6)
O1—C1—C2—C78.3 (6)C7—C8—C17—C2263.9 (7)
C6—C1—C2—C7178.4 (4)N1—C8—C17—C1867.1 (7)
O2—C2—C3—C464.7 (5)C7—C8—C17—C18114.7 (6)
C7—C2—C3—C4177.2 (4)C22—C17—C18—C191.0 (8)
C1—C2—C3—C451.8 (5)C8—C17—C18—C19179.6 (5)
C2—C3—C4—C557.9 (6)C22—C17—C18—Cl2178.8 (4)
C3—C4—C5—C659.2 (5)C8—C17—C18—Cl20.2 (7)
N2—O3—C6—C5152.1 (3)C17—C18—C19—C201.8 (9)
N2—O3—C6—C191.9 (4)Cl2—C18—C19—C20178.1 (5)
N2—O3—C6—C926.4 (4)C18—C19—C20—C211.0 (10)
C4—C5—C6—O3170.4 (4)C19—C20—C21—C220.5 (10)
C4—C5—C6—C153.8 (5)C20—C21—C22—C171.2 (10)
C4—C5—C6—C973.7 (5)C20—C21—C22—Cl3175.7 (5)
O1—C1—C6—O34.8 (6)C18—C17—C22—C210.5 (8)
C2—C1—C6—O3168.5 (4)C8—C17—C22—C21178.2 (5)
O1—C1—C6—C5120.6 (5)C18—C17—C22—Cl3176.4 (4)
C2—C1—C6—C552.7 (5)C8—C17—C22—Cl35.0 (7)
O1—C1—C6—C9108.0 (5)C10—C9—C23—C2841.2 (6)
C2—C1—C6—C978.7 (5)C6—C9—C23—C2870.0 (5)
O2—C2—C7—C810.8 (4)C10—C9—C23—C24140.0 (4)
C3—C2—C7—C8130.4 (4)C6—C9—C23—C24108.7 (5)
C1—C2—C7—C8105.0 (4)C28—C23—C24—C252.5 (6)
O2—C2—C7—C11113.6 (4)C9—C23—C24—C25178.7 (4)
C3—C2—C7—C116.0 (6)C23—C24—C25—C261.2 (6)
C1—C2—C7—C11130.6 (4)C24—C25—C26—C274.7 (7)
O2—N1—C8—C70.9 (5)C24—C25—C26—Cl4175.9 (3)
O2—N1—C8—C17179.3 (4)C25—C26—C27—C284.4 (7)
C11—C7—C8—N1119.4 (4)Cl4—C26—C27—C28176.1 (3)
C2—C7—C8—N16.5 (5)C26—C27—C28—C230.6 (7)
C11—C7—C8—C1762.3 (6)C24—C23—C28—C272.8 (7)
C2—C7—C8—C17171.8 (4)C9—C23—C28—C27178.5 (4)
O3—C6—C9—C1024.6 (4)N2—C10—C29—C30110.2 (5)
C5—C6—C9—C10142.8 (4)C9—C10—C29—C3070.1 (6)
C1—C6—C9—C1091.5 (4)N2—C10—C29—C3468.9 (6)
O3—C6—C9—C2395.2 (4)C9—C10—C29—C34110.9 (5)
C5—C6—C9—C2323.0 (6)C34—C29—C30—C311.5 (8)
C1—C6—C9—C23148.6 (4)C10—C29—C30—C31179.4 (5)
O3—N2—C10—C29178.3 (4)C34—C29—C30—Cl5177.8 (4)
O3—N2—C10—C91.9 (5)C10—C29—C30—Cl51.3 (7)
C23—C9—C10—N2104.2 (5)C29—C30—C31—C320.6 (9)
C6—C9—C10—N217.3 (5)Cl5—C30—C31—C32178.7 (5)
C23—C9—C10—C2975.6 (5)C30—C31—C32—C330.2 (10)
C6—C9—C10—C29162.9 (4)C31—C32—C33—C340.7 (10)
C8—C7—C11—C1247.9 (6)C32—C33—C34—C291.7 (9)
C2—C7—C11—C1268.5 (6)C32—C33—C34—Cl6178.2 (5)
C8—C7—C11—C16134.9 (5)C30—C29—C34—C332.0 (7)
C2—C7—C11—C16108.8 (5)C10—C29—C34—C33178.9 (5)
C16—C11—C12—C130.2 (8)C30—C29—C34—Cl6177.9 (4)
C7—C11—C12—C13177.4 (5)C10—C29—C34—Cl61.1 (7)

Experimental details

Crystal data
Chemical formulaC34H22Cl6N2O3·0.75H2O
Mr732.75
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.834 (3), 10.304 (3), 20.576 (6)
α, β, γ (°)91.915 (7), 96.371 (7), 110.718 (10)
V3)1735.7 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.53
Crystal size (mm)0.24 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.770, 0.918
No. of measured, independent and
observed [I > 2σ(I)] reflections
8673, 5928, 3052
Rint0.034
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.186, 1.02
No. of reflections5928
No. of parameters421
No. of restraints49
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.42

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

Selected geometric parameters (Å, º) top
N1—C81.267 (6)C1—C21.547 (7)
N1—O21.427 (5)C2—C31.524 (6)
O1—C11.187 (5)C2—C71.546 (6)
O2—C21.450 (5)C7—C81.497 (7)
Cl1—C141.746 (7)C7—C111.523 (6)
Cl2—C181.740 (6)
C8—N1—O2108.7 (4)O3—C6—C9103.0 (4)
C10—N2—O3108.6 (4)C5—C6—C9118.4 (4)
N1—O2—C2109.3 (3)C1—C6—C9111.5 (4)
N2—O3—C6108.8 (3)C8—C7—C11114.8 (4)
O1—C1—C6120.8 (4)C8—C7—C299.7 (4)
O1—C1—C2121.5 (4)C11—C7—C2117.0 (4)
C6—C1—C2117.3 (4)N1—C8—C7115.9 (4)
O2—C2—C3107.9 (4)N1—C8—C17118.9 (4)
O2—C2—C7105.0 (3)C7—C8—C17125.2 (4)
C3—C2—C7117.1 (4)C10—C9—C23112.8 (4)
O2—C2—C1107.8 (3)C10—C9—C698.0 (3)
C3—C2—C1108.6 (4)C23—C9—C6115.0 (4)
C7—C2—C1110.1 (4)N2—C10—C29119.8 (4)
O3—C6—C5107.3 (4)N2—C10—C9114.3 (4)
O3—C6—C1108.5 (4)C29—C10—C9126.0 (4)
C5—C6—C1107.6 (4)
 

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