4,11-Bis(4-chloro­phenyl)-3,10-bis(2,6-di­chloro­phenyl)-1,8-dioxa-2,9-di­aza­di­spiro­[4.1.4.2]­trideca-2,9-dien-6-one–chloro­form–methanol (1/1/0.75)

Li, X.-F.; Feng, Y.-Q.; Xiao-Fen, H.

doi:10.1107/S1600536803005543

4,11-Bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9-diazadispiro[4.1.4.2]trideca-2,9-dien-6-one-chloroform-methanol (1/1/0.75)

The title compound, C₃₂H₂₀Cl₆N₂O₃·CHCl₃·0.75CH₄O, was synthesized by the intermolecular [3 + 2]-cycloaddition of 2,6-dichlorobenzonitrile oxide and 2,5-bis(4-chlorobenzylidene)cyclopentanone. There are three five-membered rings linked by two spiro-C atoms, with approximate C₂ symmetry. The cyclopentane ring has a twist conformation and the two isoxazoline rings are envelopes.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005543/ww6065sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005543/ww6065Isup2.hkl Contains datablock I

CCDC reference: 214621

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
H-atom completeness 88%
Disorder in solvent or counterion
R factor = 0.056
wR factor = 0.195
Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      27.00 Perc.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #    118
                   C35 -O4  -O5  -O4   -127.00 54.00   1.555   1.555   1.555   2.667

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:C34.75 H24 Cl9 N2 O3.75
          Atom count from the _atom_site data:  C34.75 H21 Cl9 N2 O3.75

CELLZ_01
         From the CIF: _cell_formula_units_Z    2
         From the CIF: _chemical_formula_sum  C34.75 H24 Cl9 N2 O3.75
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         69.50     69.50    0.00
         H         48.00     42.00    6.00
         Cl        18.00     18.00    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

 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).

Compound (I) contains three spiro-linked rings, namely a cyclopentanone ring and two isoxazoline rings. The five-membered cyclopentanone ring has a twist 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. O2—N1—C7—C6 (ring A) and O3—N2—C21—C20 (ring B) form almost exactly planar arrangements; the torsion angle O2—N1—C7—C6 of −2.9 (5)° and O3—N2—C21—C20 of −3.0 (5)° are different from that of −0.9 (5)° in a related structure, viz. 4,11-bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9- diazadispiro[4.1.4.3]tetradeca-2,9-dien-6-one 0.75-hydrate (Li et al., 2003). Spiro-atom C2 lies 0.168 (3) Å from the O2/N1/C7/C6 plane in ring A and C5 is 0.345 (3) Å from the O3/N2/C21/C20 plane in ring B, these two atoms forming the flaps of the envelopes.

The bond lengths O2—N1 and O3—N2 are both 1.410 (4) Å, comparable to that of 1.413 (2) Å in a related structure, viz. 8-methyl-3-phenyl-1-oxa-2,8-diaza-spiro[4.5]dec-2-ene (Feng et al., 1997).

The dihedral angle between the two substituted phenyl rings on ring A is 94.9 (3)°, while that between the two substituted phenyl rings on ring B is 74.8 (3)°. The dihedral angle between the two isoxazoline ring envelope flaps (C6/C2/O2 and C20/C5/O3), which form the spiro linkages with the central ring, is 44.5 (3)°.

Experimental top

A mixture of 2,6-dichlorobenzonitrile oxide (3 mmol) and 2,5-bis(4-chlorobenzylidene)cyclopentanone (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. 535–536 K; IR (KBr): 1765 (C═O), 1595, 1581 (C═N and C═C) cm⁻¹; ¹H NMR (CDCl₃, p.p.m.): 1.77–1.81 (2H, m), 1.99–2.02 (2H, m), 5.62 (2H, s), 7.18–7.37 (14H, m); 20 mg of (I) was dissolved in 15 ml chloroform and methanol mixed solvent, and the solution was kept at room temperature for 10 d, to give colorless single crystals of (I) by evaporation.

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

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. The crystal structure of (I), viewed along the a axis, omitting the solvent molecules.

4,11-Bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9- diazadispiro[4.1.4.2]trideca-2,9-dien-6-one chloroform methanol solvate top

Crystal data top

C₃₃H₂₀Cl₆N₂O₃·CHCl₃·0.75CH₄O	Z = 2
M_r = 848.61	F(000) = 859
Triclinic, P1	D_x = 1.456 Mg m⁻³
Hall symbol: -P 1	Melting point = 535–536 K
a = 9.896 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.724 (4) Å	Cell parameters from 983 reflections
c = 15.550 (5) Å	θ = 3.2–25.4°
α = 111.815 (5)°	µ = 0.69 mm⁻¹
β = 101.814 (5)°	T = 293 K
γ = 103.510 (5)°	Plate, colorless
V = 1935.5 (10) Å³	0.28 × 0.18 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6787 independent reflections
Radiation source: fine-focus sealed tube	4617 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
T_min = 0.804, T_max = 0.908	k = −16→17
10032 measured reflections	l = −18→14

Refinement top

Refinement on F²	49 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.195	(Δ/σ)_max = 0.001
S = 1.10	Δρ_max = 0.87 e Å⁻³
6787 reflections	Δρ_min = −0.39 e Å⁻³
467 parameters

Crystal data top

C₃₃H₂₀Cl₆N₂O₃·CHCl₃·0.75CH₄O	γ = 103.510 (5)°
M_r = 848.61	V = 1935.5 (10) Å³
Triclinic, P1	Z = 2
a = 9.896 (3) Å	Mo Kα radiation
b = 14.724 (4) Å	µ = 0.69 mm⁻¹
c = 15.550 (5) Å	T = 293 K
α = 111.815 (5)°	0.28 × 0.18 × 0.14 mm
β = 101.814 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6787 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4617 reflections with I > 2σ(I)
T_min = 0.804, T_max = 0.908	R_int = 0.020
10032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	49 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.10	Δρ_max = 0.87 e Å⁻³
6787 reflections	Δρ_min = −0.39 e Å⁻³
467 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	1.43071 (16)	0.80436 (12)	0.93787 (13)	0.0848 (5)
Cl2	0.80995 (15)	0.47773 (11)	0.48562 (10)	0.0645 (4)
Cl3	0.5833 (2)	0.55659 (15)	0.78489 (13)	0.0894 (5)
Cl4	0.62958 (18)	−0.23588 (12)	0.36408 (10)	0.0832 (5)
Cl5	1.21776 (17)	0.04500 (14)	0.83836 (12)	0.0828 (5)
Cl6	0.69207 (15)	0.00826 (11)	0.89947 (11)	0.0703 (4)
O1	0.7322 (4)	0.2990 (3)	0.8195 (3)	0.0656 (10)
O2	0.7584 (3)	0.2869 (2)	0.6236 (2)	0.0473 (7)
O3	1.0241 (3)	0.2756 (2)	0.8806 (2)	0.0504 (8)
N1	0.6962 (4)	0.3497 (3)	0.5905 (3)	0.0429 (8)
N2	1.0459 (4)	0.1997 (3)	0.9111 (3)	0.0480 (9)
C1	0.8236 (5)	0.2923 (3)	0.7803 (3)	0.0405 (10)
C2	0.8673 (5)	0.3514 (3)	0.7219 (3)	0.0382 (9)
C3	1.0151 (5)	0.3413 (3)	0.7165 (4)	0.0476 (11)
H3A	1.0942	0.3945	0.7746	0.057*
H3B	1.0334	0.3466	0.6593	0.057*
C4	1.0001 (5)	0.2323 (3)	0.7095 (3)	0.0450 (10)
H4A	0.9444	0.1790	0.6435	0.054*
H4B	1.0959	0.2259	0.7283	0.054*
C5	0.9193 (5)	0.2231 (3)	0.7806 (3)	0.0393 (9)
C6	0.8462 (4)	0.4586 (3)	0.7540 (3)	0.0360 (9)
H6	0.7927	0.4662	0.8013	0.043*
C7	0.7448 (4)	0.4427 (3)	0.6582 (3)	0.0361 (9)
C8	0.9889 (5)	0.5500 (3)	0.7996 (3)	0.0377 (9)
C9	1.0475 (5)	0.6066 (3)	0.9004 (3)	0.0472 (11)
H9	0.9949	0.5918	0.9396	0.057*
C10	1.1826 (6)	0.6843 (4)	0.9433 (3)	0.0560 (12)
H10	1.2214	0.7217	1.0111	0.067*
C11	1.2597 (5)	0.7062 (4)	0.8849 (4)	0.0506 (11)
C12	1.2032 (5)	0.6521 (4)	0.7852 (4)	0.0522 (11)
H12	1.2561	0.6674	0.7464	0.063*
C13	1.0679 (5)	0.5749 (3)	0.7427 (3)	0.0477 (11)
H13	1.0290	0.5388	0.6749	0.057*
C14	0.6989 (4)	0.5233 (3)	0.6367 (3)	0.0413 (10)
C15	0.7234 (5)	0.5449 (4)	0.5600 (3)	0.0488 (11)
C16	0.6810 (6)	0.6204 (4)	0.5403 (4)	0.0652 (15)
H16	0.6985	0.6333	0.4888	0.078*
C17	0.6124 (6)	0.6761 (4)	0.5982 (5)	0.0744 (17)
H17	0.5849	0.7274	0.5858	0.089*
C18	0.5846 (6)	0.6569 (4)	0.6731 (4)	0.0659 (15)
H18	0.5374	0.6943	0.7113	0.079*
C19	0.6272 (5)	0.5814 (4)	0.6918 (4)	0.0528 (12)
C20	0.8377 (4)	0.1155 (3)	0.7700 (3)	0.0372 (9)
H20	0.7505	0.1191	0.7898	0.045*
C21	0.9490 (5)	0.1117 (3)	0.8510 (3)	0.0398 (9)
C22	0.7882 (4)	0.0254 (3)	0.6694 (3)	0.0371 (9)
C23	0.8840 (5)	−0.0169 (4)	0.6304 (3)	0.0493 (11)
H23	0.9827	0.0085	0.6675	0.059*
C24	0.8357 (5)	−0.0975 (4)	0.5360 (3)	0.0522 (12)
H24	0.9015	−0.1253	0.5100	0.063*
C25	0.6894 (5)	−0.1351 (3)	0.4818 (3)	0.0488 (11)
C26	0.5906 (5)	−0.0948 (4)	0.5189 (3)	0.0494 (11)
H26	0.4919	−0.1212	0.4816	0.059*
C27	0.6400 (5)	−0.0143 (3)	0.6126 (3)	0.0451 (10)
H27	0.5738	0.0136	0.6380	0.054*
C28	0.9493 (5)	0.0167 (3)	0.8628 (3)	0.0442 (11)
C29	1.0644 (6)	−0.0218 (4)	0.8551 (3)	0.0591 (13)
C30	1.0588 (9)	−0.1149 (5)	0.8610 (4)	0.082 (2)
H30	1.1353	−0.1406	0.8539	0.099*
C31	0.9427 (10)	−0.1682 (5)	0.8770 (4)	0.092 (2)
H31	0.9401	−0.2303	0.8803	0.110*
C32	0.8290 (8)	−0.1315 (4)	0.8884 (4)	0.0759 (18)
H32	0.7508	−0.1672	0.9012	0.091*
C33	0.8329 (6)	−0.0396 (4)	0.8804 (3)	0.0562 (13)
C34	0.2388 (5)	0.8183 (4)	0.5982 (3)	0.0537 (12)
H34	0.2587	0.7695	0.5434	0.064*
Cl7	0.06771 (16)	0.75603 (13)	0.60192 (14)	0.0853 (5)
Cl8	0.23653 (15)	0.92778 (11)	0.57808 (10)	0.0666 (4)
Cl9	0.37803 (15)	0.85353 (12)	0.70606 (10)	0.0685 (4)
O4	0.4023 (19)	0.4088 (13)	0.8868 (14)	0.192 (5)	0.50
C35	0.4291 (18)	0.3249 (15)	0.9069 (13)	0.126 (5)	0.50
O5	0.5000	0.5000	1.0000	0.160 (6)	0.50
C36	0.354 (2)	0.504 (3)	0.992 (3)	0.135 (9)	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0544 (8)	0.0721 (10)	0.0903 (11)	−0.0021 (7)	0.0050 (8)	0.0209 (8)
Cl2	0.0686 (8)	0.0847 (9)	0.0585 (7)	0.0304 (7)	0.0291 (6)	0.0432 (7)
Cl3	0.1173 (13)	0.1138 (13)	0.0987 (12)	0.0812 (11)	0.0748 (11)	0.0646 (10)
Cl4	0.0803 (10)	0.0779 (10)	0.0473 (7)	0.0046 (8)	0.0114 (7)	0.0002 (7)
Cl5	0.0749 (10)	0.1027 (12)	0.0828 (10)	0.0555 (9)	0.0256 (8)	0.0379 (9)
Cl6	0.0626 (8)	0.0763 (9)	0.0743 (9)	0.0117 (7)	0.0186 (7)	0.0446 (8)
O1	0.084 (2)	0.074 (2)	0.093 (3)	0.053 (2)	0.063 (2)	0.060 (2)
O2	0.064 (2)	0.0342 (15)	0.0413 (16)	0.0199 (14)	0.0103 (15)	0.0154 (13)
O3	0.0608 (19)	0.0349 (16)	0.0466 (17)	0.0123 (14)	0.0025 (15)	0.0189 (14)
N1	0.048 (2)	0.043 (2)	0.043 (2)	0.0189 (17)	0.0134 (17)	0.0226 (17)
N2	0.058 (2)	0.043 (2)	0.042 (2)	0.0199 (19)	0.0078 (18)	0.0206 (18)
C1	0.049 (2)	0.039 (2)	0.042 (2)	0.0198 (19)	0.018 (2)	0.0219 (19)
C2	0.044 (2)	0.037 (2)	0.038 (2)	0.0174 (18)	0.0152 (19)	0.0182 (18)
C3	0.050 (3)	0.044 (2)	0.056 (3)	0.018 (2)	0.025 (2)	0.024 (2)
C4	0.044 (2)	0.044 (2)	0.058 (3)	0.024 (2)	0.023 (2)	0.025 (2)
C5	0.043 (2)	0.038 (2)	0.038 (2)	0.0158 (18)	0.0119 (18)	0.0175 (18)
C6	0.046 (2)	0.034 (2)	0.037 (2)	0.0186 (18)	0.0190 (18)	0.0196 (17)
C7	0.040 (2)	0.035 (2)	0.037 (2)	0.0146 (18)	0.0141 (18)	0.0179 (18)
C8	0.047 (2)	0.032 (2)	0.038 (2)	0.0170 (18)	0.0116 (18)	0.0182 (17)
C9	0.062 (3)	0.044 (2)	0.037 (2)	0.019 (2)	0.017 (2)	0.017 (2)
C10	0.060 (3)	0.052 (3)	0.037 (2)	0.014 (2)	0.004 (2)	0.010 (2)
C11	0.044 (3)	0.043 (3)	0.057 (3)	0.013 (2)	0.008 (2)	0.020 (2)
C12	0.053 (3)	0.052 (3)	0.054 (3)	0.014 (2)	0.018 (2)	0.028 (2)
C13	0.056 (3)	0.046 (3)	0.037 (2)	0.008 (2)	0.012 (2)	0.020 (2)
C14	0.038 (2)	0.038 (2)	0.050 (2)	0.0127 (18)	0.0093 (19)	0.0232 (19)
C15	0.040 (2)	0.053 (3)	0.055 (3)	0.013 (2)	0.008 (2)	0.031 (2)
C16	0.056 (3)	0.071 (4)	0.076 (4)	0.018 (3)	0.006 (3)	0.051 (3)
C17	0.067 (3)	0.061 (3)	0.102 (5)	0.030 (3)	0.006 (3)	0.050 (3)
C18	0.058 (3)	0.058 (3)	0.083 (4)	0.032 (3)	0.015 (3)	0.030 (3)
C19	0.050 (3)	0.053 (3)	0.063 (3)	0.025 (2)	0.018 (2)	0.028 (2)
C20	0.041 (2)	0.038 (2)	0.040 (2)	0.0179 (18)	0.0111 (18)	0.0216 (18)
C21	0.046 (2)	0.041 (2)	0.034 (2)	0.020 (2)	0.0090 (19)	0.0179 (19)
C22	0.040 (2)	0.035 (2)	0.038 (2)	0.0137 (18)	0.0071 (18)	0.0207 (18)
C23	0.043 (2)	0.052 (3)	0.047 (3)	0.020 (2)	0.004 (2)	0.019 (2)
C24	0.055 (3)	0.052 (3)	0.044 (2)	0.024 (2)	0.012 (2)	0.014 (2)
C25	0.056 (3)	0.043 (2)	0.040 (2)	0.009 (2)	0.010 (2)	0.017 (2)
C26	0.038 (2)	0.051 (3)	0.048 (3)	0.004 (2)	0.004 (2)	0.023 (2)
C27	0.039 (2)	0.048 (3)	0.050 (3)	0.014 (2)	0.012 (2)	0.025 (2)
C28	0.063 (3)	0.038 (2)	0.031 (2)	0.025 (2)	0.006 (2)	0.0153 (18)
C29	0.082 (4)	0.055 (3)	0.039 (2)	0.034 (3)	0.008 (2)	0.019 (2)
C30	0.135 (6)	0.068 (4)	0.051 (3)	0.069 (4)	0.012 (4)	0.022 (3)
C31	0.170 (8)	0.046 (3)	0.058 (3)	0.043 (4)	0.015 (4)	0.028 (3)
C32	0.118 (5)	0.043 (3)	0.054 (3)	0.014 (3)	0.009 (3)	0.026 (2)
C33	0.080 (4)	0.039 (2)	0.037 (2)	0.013 (2)	0.005 (2)	0.016 (2)
C34	0.062 (3)	0.056 (3)	0.048 (3)	0.025 (2)	0.021 (2)	0.023 (2)
Cl7	0.0625 (9)	0.0808 (10)	0.1117 (13)	0.0098 (7)	0.0162 (8)	0.0567 (10)
Cl8	0.0662 (8)	0.0770 (9)	0.0775 (9)	0.0284 (7)	0.0251 (7)	0.0522 (8)
Cl9	0.0648 (8)	0.0807 (9)	0.0688 (8)	0.0330 (7)	0.0145 (7)	0.0407 (7)
O4	0.166 (9)	0.175 (8)	0.202 (9)	0.020 (7)	0.081 (7)	0.061 (6)
C35	0.084 (8)	0.147 (8)	0.118 (9)	0.047 (7)	0.031 (7)	0.024 (6)
O5	0.158 (9)	0.164 (8)	0.151 (9)	0.079 (8)	0.033 (7)	0.056 (7)
C36	0.129 (11)	0.135 (13)	0.142 (13)	0.054 (10)	0.023 (9)	0.068 (8)

Geometric parameters (Å, º) top

Cl1—C11	1.742 (5)	C15—C16	1.386 (7)
Cl2—C15	1.733 (5)	C16—C17	1.379 (8)
Cl3—C19	1.730 (5)	C16—H16	0.9300
Cl4—C25	1.741 (5)	C17—C18	1.360 (9)
Cl5—C29	1.730 (6)	C17—H17	0.9300
Cl6—C33	1.731 (6)	C18—C19	1.382 (7)
O1—C1	1.192 (5)	C18—H18	0.9300
O2—N1	1.410 (4)	C20—C22	1.513 (6)
O2—C2	1.472 (5)	C20—C21	1.521 (5)
O3—N2	1.410 (4)	C20—H20	0.9800
O3—C5	1.471 (5)	C21—C28	1.476 (6)
N1—C7	1.276 (5)	C22—C23	1.373 (6)
N2—C21	1.274 (6)	C22—C27	1.400 (6)
C1—C2	1.531 (6)	C23—C24	1.394 (6)
C1—C5	1.544 (6)	C23—H23	0.9300
C2—C3	1.521 (6)	C24—C25	1.375 (6)
C2—C6	1.547 (5)	C24—H24	0.9300
C3—C4	1.537 (6)	C25—C26	1.374 (7)
C3—H3A	0.9700	C26—C27	1.385 (6)
C3—H3B	0.9700	C26—H26	0.9300
C4—C5	1.517 (6)	C27—H27	0.9300
C4—H4A	0.9700	C28—C33	1.393 (7)
C4—H4B	0.9700	C28—C29	1.393 (7)
C5—C20	1.532 (6)	C29—C30	1.397 (8)
C6—C7	1.516 (5)	C30—C31	1.356 (10)
C6—C8	1.517 (6)	C30—H30	0.9300
C6—H6	0.9800	C31—C32	1.372 (10)
C7—C14	1.487 (5)	C31—H31	0.9300
C8—C13	1.384 (6)	C32—C33	1.397 (7)
C8—C9	1.386 (6)	C32—H32	0.9300
C9—C10	1.377 (7)	C34—Cl9	1.748 (5)
C9—H9	0.9300	C34—Cl7	1.751 (5)
C10—C11	1.377 (7)	C34—Cl8	1.756 (5)
C10—H10	0.9300	C34—H34	0.9800
C11—C12	1.368 (7)	O4—C35	1.449 (10)
C12—C13	1.374 (6)	O4—O5	1.667 (18)
C12—H12	0.9300	O5—C36ⁱ	1.438 (10)
C13—H13	0.9300	O5—C36	1.438 (10)
C14—C15	1.395 (6)	O5—O4ⁱ	1.667 (18)
C14—C19	1.399 (6)

N1—O2—C2	109.9 (3)	C18—C17—C16	120.9 (5)
N2—O3—C5	108.9 (3)	C18—C17—H17	119.6
C7—N1—O2	109.6 (3)	C16—C17—H17	119.6
C21—N2—O3	109.1 (3)	C17—C18—C19	119.3 (5)
O1—C1—C2	125.9 (4)	C17—C18—H18	120.3
O1—C1—C5	125.8 (4)	C19—C18—H18	120.3
C2—C1—C5	108.2 (3)	C18—C19—C14	122.6 (5)
O2—C2—C3	108.1 (3)	C18—C19—Cl3	117.6 (4)
O2—C2—C1	103.3 (3)	C14—C19—Cl3	119.8 (3)
C3—C2—C1	103.7 (3)	C22—C20—C21	116.7 (3)
O2—C2—C6	104.5 (3)	C22—C20—C5	116.8 (3)
C3—C2—C6	120.8 (4)	C21—C20—C5	99.2 (3)
C1—C2—C6	115.0 (3)	C22—C20—H20	107.8
C2—C3—C4	103.6 (3)	C21—C20—H20	107.8
C2—C3—H3A	111.0	C5—C20—H20	107.8
C4—C3—H3A	111.0	N2—C21—C28	120.8 (4)
C2—C3—H3B	111.0	N2—C21—C20	114.2 (4)
C4—C3—H3B	111.0	C28—C21—C20	125.0 (4)
H3A—C3—H3B	109.0	C23—C22—C27	118.6 (4)
C5—C4—C3	104.4 (3)	C23—C22—C20	122.5 (4)
C5—C4—H4A	110.9	C27—C22—C20	118.8 (4)
C3—C4—H4A	110.9	C22—C23—C24	121.0 (4)
C5—C4—H4B	110.9	C22—C23—H23	119.5
C3—C4—H4B	110.9	C24—C23—H23	119.5
H4A—C4—H4B	108.9	C25—C24—C23	119.1 (4)
O3—C5—C4	109.4 (3)	C25—C24—H24	120.5
O3—C5—C20	103.7 (3)	C23—C24—H24	120.5
C4—C5—C20	119.8 (3)	C26—C25—C24	121.3 (4)
O3—C5—C1	104.3 (3)	C26—C25—Cl4	119.8 (4)
C4—C5—C1	104.1 (3)	C24—C25—Cl4	118.9 (4)
C20—C5—C1	114.5 (3)	C25—C26—C27	119.2 (4)
C7—C6—C8	116.2 (3)	C25—C26—H26	120.4
C7—C6—C2	100.1 (3)	C27—C26—H26	120.4
C8—C6—C2	113.8 (3)	C26—C27—C22	120.8 (4)
C7—C6—H6	108.8	C26—C27—H27	119.6
C8—C6—H6	108.8	C22—C27—H27	119.6
C2—C6—H6	108.8	C33—C28—C29	116.9 (4)
N1—C7—C14	118.4 (4)	C33—C28—C21	121.4 (4)
N1—C7—C6	114.8 (3)	C29—C28—C21	121.7 (4)
C14—C7—C6	126.8 (3)	C28—C29—C30	120.8 (6)
C13—C8—C9	118.5 (4)	C28—C29—Cl5	120.6 (4)
C13—C8—C6	121.3 (4)	C30—C29—Cl5	118.6 (5)
C9—C8—C6	120.1 (4)	C31—C30—C29	120.5 (6)
C10—C9—C8	120.8 (4)	C31—C30—H30	119.7
C10—C9—H9	119.6	C29—C30—H30	119.7
C8—C9—H9	119.6	C30—C31—C32	120.8 (5)
C9—C10—C11	119.3 (4)	C30—C31—H31	119.6
C9—C10—H10	120.3	C32—C31—H31	119.6
C11—C10—H10	120.3	C31—C32—C33	118.7 (6)
C12—C11—C10	120.8 (4)	C31—C32—H32	120.6
C12—C11—Cl1	119.2 (4)	C33—C32—H32	120.6
C10—C11—Cl1	120.0 (4)	C28—C33—C32	122.2 (6)
C11—C12—C13	119.6 (5)	C28—C33—Cl6	119.6 (3)
C11—C12—H12	120.2	C32—C33—Cl6	118.2 (5)
C13—C12—H12	120.2	Cl9—C34—Cl7	110.8 (3)
C12—C13—C8	120.9 (4)	Cl9—C34—Cl8	110.7 (3)
C12—C13—H13	119.6	Cl7—C34—Cl8	110.5 (3)
C8—C13—H13	119.6	Cl9—C34—H34	108.3
C15—C14—C19	115.9 (4)	Cl7—C34—H34	108.3
C15—C14—C7	122.2 (4)	Cl8—C34—H34	108.3
C19—C14—C7	121.8 (4)	C35—O4—O5	93.8 (13)
C16—C15—C14	122.1 (5)	C36ⁱ—O5—C36	180.000 (15)
C16—C15—Cl2	117.4 (4)	C36ⁱ—O5—O4	102.6 (18)
C14—C15—Cl2	120.5 (3)	C36—O5—O4	77.4 (18)
C17—C16—C15	119.2 (5)	C36ⁱ—O5—O4ⁱ	77.4 (18)
C17—C16—H16	120.4	C36—O5—O4ⁱ	102.6 (18)
C15—C16—H16	120.4	O4—O5—O4ⁱ	180.000 (7)

C2—O2—N1—C7	−4.7 (4)	C19—C14—C15—Cl2	−179.5 (3)
C5—O3—N2—C21	−12.0 (5)	C7—C14—C15—Cl2	−0.1 (6)
N1—O2—C2—C3	−120.1 (3)	C14—C15—C16—C17	0.0 (8)
N1—O2—C2—C1	130.4 (3)	Cl2—C15—C16—C17	−179.6 (4)
N1—O2—C2—C6	9.7 (4)	C15—C16—C17—C18	−0.8 (8)
O1—C1—C2—O2	−84.5 (5)	C16—C17—C18—C19	0.7 (9)
C5—C1—C2—O2	96.1 (4)	C17—C18—C19—C14	0.2 (8)
O1—C1—C2—C3	162.8 (5)	C17—C18—C19—Cl3	−177.7 (4)
C5—C1—C2—C3	−16.7 (4)	C15—C14—C19—C18	−0.9 (7)
O1—C1—C2—C6	28.7 (6)	C7—C14—C19—C18	179.7 (4)
C5—C1—C2—C6	−150.8 (3)	C15—C14—C19—Cl3	176.9 (3)
O2—C2—C3—C4	−74.5 (4)	C7—C14—C19—Cl3	−2.6 (6)
C1—C2—C3—C4	34.7 (4)	O3—C5—C20—C22	−146.8 (3)
C6—C2—C3—C4	165.4 (4)	C4—C5—C20—C22	−24.6 (5)
C2—C3—C4—C5	−40.7 (4)	C1—C5—C20—C22	100.2 (4)
N2—O3—C5—C4	−107.8 (4)	O3—C5—C20—C21	−20.5 (4)
N2—O3—C5—C20	21.1 (4)	C4—C5—C20—C21	101.7 (4)
N2—O3—C5—C1	141.3 (3)	C1—C5—C20—C21	−133.5 (3)
C3—C4—C5—O3	−81.5 (4)	O3—N2—C21—C28	177.4 (4)
C3—C4—C5—C20	159.1 (4)	O3—N2—C21—C20	−3.0 (5)
C3—C4—C5—C1	29.6 (4)	C22—C20—C21—N2	141.8 (4)
O1—C1—C5—O3	−72.9 (5)	C5—C20—C21—N2	15.5 (5)
C2—C1—C5—O3	106.6 (4)	C22—C20—C21—C28	−38.5 (6)
O1—C1—C5—C4	172.4 (5)	C5—C20—C21—C28	−164.9 (4)
C2—C1—C5—C4	−8.1 (4)	C21—C20—C22—C23	−42.4 (6)
O1—C1—C5—C20	39.7 (6)	C5—C20—C22—C23	74.7 (5)
C2—C1—C5—C20	−140.8 (3)	C21—C20—C22—C27	139.6 (4)
O2—C2—C6—C7	−10.2 (4)	C5—C20—C22—C27	−103.3 (4)
C3—C2—C6—C7	111.6 (4)	C27—C22—C23—C24	0.3 (7)
C1—C2—C6—C7	−122.7 (4)	C20—C22—C23—C24	−177.6 (4)
O2—C2—C6—C8	−134.8 (3)	C22—C23—C24—C25	−0.4 (7)
C3—C2—C6—C8	−13.0 (5)	C23—C24—C25—C26	0.1 (7)
C1—C2—C6—C8	112.7 (4)	C23—C24—C25—Cl4	−179.8 (4)
O2—N1—C7—C14	176.8 (3)	C24—C25—C26—C27	0.3 (7)
O2—N1—C7—C6	−2.9 (5)	Cl4—C25—C26—C27	−179.8 (3)
C8—C6—C7—N1	131.5 (4)	C25—C26—C27—C22	−0.4 (7)
C2—C6—C7—N1	8.5 (5)	C23—C22—C27—C26	0.1 (6)
C8—C6—C7—C14	−48.1 (5)	C20—C22—C27—C26	178.1 (4)
C2—C6—C7—C14	−171.1 (4)	N2—C21—C28—C33	117.0 (5)
C7—C6—C8—C13	−39.8 (5)	C20—C21—C28—C33	−62.6 (6)
C2—C6—C8—C13	75.7 (5)	N2—C21—C28—C29	−64.1 (6)
C7—C6—C8—C9	144.3 (4)	C20—C21—C28—C29	116.3 (5)
C2—C6—C8—C9	−100.3 (4)	C33—C28—C29—C30	2.5 (7)
C13—C8—C9—C10	−1.3 (6)	C21—C28—C29—C30	−176.4 (4)
C6—C8—C9—C10	174.7 (4)	C33—C28—C29—Cl5	−177.3 (3)
C8—C9—C10—C11	0.3 (7)	C21—C28—C29—Cl5	3.8 (6)
C9—C10—C11—C12	0.4 (7)	C28—C29—C30—C31	−1.8 (8)
C9—C10—C11—Cl1	180.0 (4)	Cl5—C29—C30—C31	178.1 (5)
C10—C11—C12—C13	0.0 (7)	C29—C30—C31—C32	−0.4 (9)
Cl1—C11—C12—C13	−179.6 (4)	C30—C31—C32—C33	1.8 (9)
C11—C12—C13—C8	−1.0 (7)	C29—C28—C33—C32	−1.1 (7)
C9—C8—C13—C12	1.7 (6)	C21—C28—C33—C32	177.8 (4)
C6—C8—C13—C12	−174.3 (4)	C29—C28—C33—Cl6	175.4 (3)
N1—C7—C14—C15	−57.0 (6)	C21—C28—C33—Cl6	−5.7 (6)
C6—C7—C14—C15	122.6 (5)	C31—C32—C33—C28	−1.0 (8)
N1—C7—C14—C19	122.3 (5)	C31—C32—C33—Cl6	−177.6 (4)
C6—C7—C14—C19	−58.0 (6)	C35—O4—O5—C36ⁱ	64 (2)
C19—C14—C15—C16	0.8 (7)	C35—O4—O5—C36	−116 (2)
C7—C14—C15—C16	−179.8 (4)	C35—O4—O5—O4ⁱ	−127 (54)

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₃₃H₂₀Cl₆N₂O₃·CHCl₃·0.75CH₄O
M_r	848.61
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.896 (3), 14.724 (4), 15.550 (5)
α, β, γ (°)	111.815 (5), 101.814 (5), 103.510 (5)
V (Å³)	1935.5 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.28 × 0.18 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.804, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	10032, 6787, 4617
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.195, 1.10
No. of reflections	6787
No. of parameters	467
No. of restraints	49
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.39

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

Selected geometric parameters (Å, º) top

Cl1—C11	1.742 (5)	O2—N1	1.410 (4)
O1—C1	1.192 (5)	O3—N2	1.410 (4)

N1—O2—C2	109.9 (3)	O2—C2—C1	103.3 (3)
N2—O3—C5	108.9 (3)	O2—C2—C6	104.5 (3)
C7—N1—O2	109.6 (3)	O3—C5—C20	103.7 (3)
C21—N2—O3	109.1 (3)	C7—C6—C2	100.1 (3)
O1—C1—C5	125.8 (4)

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

4,11-Bis(4-chloro­phenyl)-3,10-bis(2,6-di­chloro­phenyl)-1,8-dioxa-2,9-di­aza­di­spiro­[4.1.4.2]­trideca-2,9-dien-6-one-chloro­form-methanol (1/1/0.75)

Supporting information

Key indicators

checkCIF results

4,11-Bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9-diazadispiro[4.1.4.2]trideca-2,9-dien-6-one-chloroform-methanol (1/1/0.75)