4,11-Bis(4-chloro­phenyl)-3,10-bis(2,6-di­chloro­phenyl)-1,8-dioxa-2,9-di­aza­di­spiro­[4.1.4.4]­pentadeca-2,9-dien-6-one

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

doi:10.1107/S1600536803008535

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4,11-Bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9-diazadispiro[4.1.4.4]pentadeca-2,9-dien-6-one

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

The title compound, C₃₅H₂₄Cl₆N₂O₃, which was synthesized by the [3 + 2]-cycloaddition of 2,6-dichlorobenzonitrile oxide and 2,7-bis(4-chlorobenzylidene)cycloheptanone, contains two independent molecules in the asymmetric unit. Three rings are linked by two spiro-C atoms. The cycloheptanone ring adopts a chair conformation and the two five-membered isoxazoline rings have envelope conformations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008535/cv6183sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008535/cv6183Isup2.hkl Contains datablock I

CCDC reference: 214639

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.065
wR factor = 0.099
Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      49.00 A   3


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 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 cycloheptanone ring and two isoxazoline rings. The seven-membered cycloheptanone ring has the chair conformation. The two isoxazoline rings are attached to this central ring through spiro-C atoms, with a pseudosymmetric centre at the carbonyl carbon of the cycloheptanone ring, which is different from the similar structure in literature (Li et al., 2003), which is 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/C8/C9 (ring A) and O3/N2/C10/C11 (ring B) form nearly planar arrangements. The spiro-atom C2 lies −0.440 (3) Å from the O2/N1/C8/C9 plane in ring A and C7 lies 3.019 (3) Å from the O3/N2/C10/C11 plane in ring B, forming the flaps of the envelopes. The dihedral angle between the C9/C2/O2 plane and the O2/N1/C8/C9 mean plane is 28.6 (4)°, and that between the C11/C7/O3 plane and the O3/N2/C10/C11 mean plane is 12.2 (4)°, similar to 12.0 (4) and 26.7 (4)° reported in the literature (Li et al., 2003)

The dihedral angles between the two substituted phenyl rings on rings A and B are 90.4 (3) and 104.2 (3)°, respectively. The dihedral angle between the two isoxazoline ring envelope flaps (C9/C2/O2 and C11/C7/O3), which form the spiro linkages with the central ring, is 86.7 (3)°.

The differences between the two independent molecules in the asymmetric unit are shown in Fig. 2 and Table 1.

Experimental top

A mixture of 2,6-dichlorobenzonitrile oxide (3 mmol) and 2,7-bis(4-chlorobenzylidene)cycloheptanone (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): 1718 (C═O), 1598, 1582 (C═N, C═C) cm⁻¹; ¹H NMR (CDCl₃, p.p.m.): 1.10–1.61 (4H, m), 1.71–2.22 (4H, m), 5.68 (1H, s), 5.91 (1H, s), 7.15–7.35 (14H, m); 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.

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) with 30% probability displacement ellipsoids.
	Fig. 2. The molecular fitting diagram of two independent molecules in the asymmetric unit.

4,11-Bis(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9- diazadispiro[4.1.4.4]pentadeca-2,9-dien-6-one top

Crystal data top

C₃₅H₂₄Cl₆N₂O₃	D_x = 1.427 Mg m⁻³
M_r = 733.26	Melting point = 535–536 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 33.510 (9) Å	Cell parameters from 914 reflections
b = 12.419 (5) Å	θ = 3.3–23.7°
c = 32.946 (9) Å	µ = 0.54 mm⁻¹
β = 95.152 (8)°	T = 293 K
V = 13655 (8) Å³	Plate, colorless
Z = 16	0.30 × 0.20 × 0.10 mm
F(000) = 5984

Data collection top

Bruker SMART CCD area-detector diffractometer	11983 independent reflections
Radiation source: fine-focus sealed tube	5317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −39→39
T_min = 0.835, T_max = 0.947	k = −9→14
27390 measured reflections	l = −39→35

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.065	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max = 0.001
S = 0.97	Δρ_max = 0.25 e Å⁻³
11983 reflections	Δρ_min = −0.36 e Å⁻³
829 parameters

Crystal data top

C₃₅H₂₄Cl₆N₂O₃	V = 13655 (8) Å³
M_r = 733.26	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 33.510 (9) Å	µ = 0.54 mm⁻¹
b = 12.419 (5) Å	T = 293 K
c = 32.946 (9) Å	0.30 × 0.20 × 0.10 mm
β = 95.152 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	11983 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	5317 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.947	R_int = 0.099
27390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.97	Δρ_max = 0.25 e Å⁻³
11983 reflections	Δρ_min = −0.36 e Å⁻³
829 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
Cl1	0.40710 (3)	0.83068 (11)	0.57929 (4)	0.0876 (5)
Cl2	0.46373 (4)	0.56448 (10)	0.70237 (4)	0.0810 (4)
Cl3	0.57987 (4)	0.94525 (12)	0.78535 (4)	0.0943 (5)
Cl4	0.41756 (4)	0.95667 (9)	0.47522 (5)	0.0827 (4)
Cl5	0.40670 (4)	0.54960 (10)	0.41623 (4)	0.0908 (5)
Cl6	0.55635 (4)	0.74111 (12)	0.31164 (4)	0.1024 (5)
Cl7	0.65533 (3)	0.64167 (10)	0.35321 (4)	0.0716 (4)
Cl8	0.72812 (4)	0.35607 (10)	0.46015 (4)	0.0873 (4)
Cl9	0.83983 (4)	0.70066 (13)	0.55369 (4)	0.1083 (5)
Cl10	0.63353 (4)	0.41158 (12)	0.19446 (5)	0.0994 (5)
Cl11	0.65573 (3)	0.80557 (9)	0.26534 (4)	0.0757 (4)
Cl12	0.75857 (6)	0.55152 (12)	0.06655 (4)	0.1361 (7)
N1	0.48867 (11)	0.6193 (3)	0.61244 (10)	0.0496 (9)
N2	0.44196 (9)	0.6511 (3)	0.49800 (11)	0.0451 (9)
N3	0.74391 (9)	0.4470 (2)	0.37017 (10)	0.0412 (9)
N4	0.68698 (10)	0.4954 (3)	0.26976 (10)	0.0466 (9)
O1	0.49824 (8)	0.8879 (2)	0.54396 (8)	0.0553 (8)
O2	0.52583 (8)	0.6456 (2)	0.59711 (8)	0.0464 (7)
O3	0.47821 (8)	0.63281 (19)	0.52157 (8)	0.0473 (7)
O4	0.74209 (8)	0.7388 (2)	0.31184 (8)	0.0507 (8)
O5	0.77834 (7)	0.4878 (2)	0.35331 (7)	0.0430 (7)
O6	0.72768 (8)	0.47857 (19)	0.28283 (8)	0.0438 (7)
C1	0.50866 (10)	0.7956 (3)	0.54901 (13)	0.0381 (11)
C2	0.52650 (11)	0.7611 (3)	0.59170 (12)	0.0384 (10)
C3	0.56996 (11)	0.7992 (3)	0.59522 (13)	0.0531 (12)
H3A	0.5812	0.7892	0.6231	0.064*
H3B	0.5703	0.8758	0.5894	0.064*
C4	0.59693 (11)	0.7421 (3)	0.56699 (14)	0.0571 (13)
H4A	0.6227	0.7780	0.5698	0.069*
H4B	0.6012	0.6693	0.5771	0.069*
C5	0.58375 (12)	0.7344 (3)	0.52189 (13)	0.0545 (12)
H5A	0.6062	0.7085	0.5079	0.065*
H5B	0.5773	0.8062	0.5117	0.065*
C6	0.54769 (11)	0.6612 (3)	0.51067 (12)	0.0434 (11)
H6A	0.5494	0.6341	0.4833	0.052*
H6B	0.5492	0.5999	0.5290	0.052*
C7	0.50730 (11)	0.7159 (3)	0.51264 (12)	0.0378 (10)
C8	0.47305 (12)	0.7049 (4)	0.62576 (12)	0.0450 (11)
C9	0.49937 (11)	0.8035 (3)	0.62338 (12)	0.0396 (11)
H9	0.4832	0.8633	0.6115	0.047*
C10	0.44641 (11)	0.7252 (3)	0.47215 (13)	0.0379 (10)
C11	0.48823 (11)	0.7729 (3)	0.47390 (12)	0.0371 (10)
H11	0.4863	0.8499	0.4799	0.045*
C12	0.43341 (13)	0.6990 (3)	0.64172 (14)	0.0479 (12)
C13	0.40087 (15)	0.7552 (4)	0.62269 (14)	0.0639 (14)
C14	0.36320 (15)	0.7481 (4)	0.63566 (18)	0.0811 (16)
H14	0.3420	0.7864	0.6224	0.097*
C15	0.35698 (17)	0.6833 (5)	0.66875 (19)	0.0889 (19)
H15	0.3315	0.6781	0.6778	0.107*
C16	0.38822 (18)	0.6271 (4)	0.68812 (16)	0.0758 (16)
H16	0.3839	0.5829	0.7101	0.091*
C17	0.42588 (14)	0.6358 (4)	0.67519 (14)	0.0582 (13)
C18	0.51919 (11)	0.8371 (3)	0.66433 (13)	0.0397 (11)
C19	0.51906 (12)	0.9426 (4)	0.67620 (15)	0.0629 (13)
H19	0.5066	0.9935	0.6587	0.075*
C20	0.53712 (15)	0.9756 (4)	0.71389 (18)	0.0777 (16)
H20	0.5360	1.0474	0.7217	0.093*
C21	0.55631 (12)	0.9025 (4)	0.73890 (14)	0.0549 (13)
C22	0.55705 (13)	0.7980 (4)	0.72800 (15)	0.0614 (13)
H22	0.5702	0.7478	0.7453	0.074*
C23	0.53834 (13)	0.7658 (3)	0.69127 (14)	0.0584 (13)
H23	0.5387	0.6932	0.6844	0.070*
C24	0.41272 (11)	0.7570 (3)	0.44264 (13)	0.0423 (11)
C25	0.39852 (12)	0.8617 (3)	0.44007 (14)	0.0525 (12)
C26	0.36833 (14)	0.8936 (4)	0.41124 (17)	0.0722 (16)
H26	0.3604	0.9653	0.4095	0.087*
C27	0.35019 (14)	0.8187 (5)	0.38519 (18)	0.0867 (18)
H27	0.3297	0.8395	0.3659	0.104*
C28	0.36218 (13)	0.7136 (4)	0.38757 (16)	0.0773 (16)
H28	0.3497	0.6626	0.3701	0.093*
C29	0.39279 (13)	0.6832 (3)	0.41594 (15)	0.0561 (13)
C30	0.50742 (11)	0.7609 (3)	0.43448 (13)	0.0391 (11)
C31	0.50563 (11)	0.6655 (3)	0.41262 (14)	0.0476 (12)
H31	0.4936	0.6054	0.4232	0.057*
C32	0.52136 (12)	0.6581 (4)	0.37537 (15)	0.0567 (13)
H32	0.5199	0.5937	0.3609	0.068*
C33	0.53905 (13)	0.7465 (5)	0.35993 (14)	0.0598 (14)
C34	0.54317 (13)	0.8408 (4)	0.38183 (17)	0.0666 (14)
H34	0.5567	0.8992	0.3719	0.080*
C35	0.52684 (12)	0.8473 (3)	0.41870 (14)	0.0532 (12)
H35	0.5290	0.9114	0.4333	0.064*
C36	0.75297 (10)	0.6462 (3)	0.31288 (12)	0.0346 (10)
C37	0.77538 (10)	0.6037 (3)	0.35270 (12)	0.0346 (10)
C38	0.81763 (11)	0.6520 (3)	0.35458 (12)	0.0493 (12)
H38A	0.8153	0.7297	0.3528	0.059*
H38B	0.8315	0.6350	0.3809	0.059*
C39	0.84312 (12)	0.6130 (4)	0.32132 (14)	0.0668 (14)
H39A	0.8681	0.6527	0.3240	0.080*
H39B	0.8496	0.5379	0.3266	0.080*
C40	0.82552 (12)	0.6223 (4)	0.27717 (13)	0.0603 (13)
H40A	0.8468	0.6124	0.2594	0.072*
H40B	0.8149	0.6944	0.2726	0.072*
C41	0.79202 (11)	0.5405 (3)	0.26522 (12)	0.0528 (12)
H41A	0.7918	0.5258	0.2363	0.063*
H41B	0.7984	0.4737	0.2796	0.063*
C42	0.75021 (11)	0.5754 (3)	0.27404 (12)	0.0355 (10)
C43	0.72768 (11)	0.5229 (3)	0.38888 (12)	0.0362 (10)
C44	0.75082 (10)	0.6287 (3)	0.38907 (11)	0.0366 (10)
H44	0.7325	0.6890	0.3825	0.044*
C45	0.68386 (12)	0.5793 (3)	0.24748 (12)	0.0396 (11)
C46	0.72329 (10)	0.6309 (3)	0.23994 (11)	0.0343 (10)
H46	0.7222	0.7085	0.2452	0.041*
C47	0.69066 (13)	0.5035 (3)	0.40897 (13)	0.0447 (11)
C48	0.65578 (14)	0.5572 (3)	0.39466 (14)	0.0567 (13)
C49	0.61994 (16)	0.5441 (4)	0.41223 (19)	0.0872 (18)
H49	0.5970	0.5805	0.4018	0.105*
C50	0.61878 (19)	0.4776 (5)	0.4447 (2)	0.103 (2)
H50	0.5950	0.4703	0.4571	0.123*
C51	0.65188 (19)	0.4211 (4)	0.45975 (17)	0.0830 (18)
H51	0.6506	0.3747	0.4817	0.100*
C52	0.68750 (15)	0.4343 (3)	0.44155 (15)	0.0604 (13)
C53	0.77419 (11)	0.6468 (3)	0.42988 (12)	0.0393 (10)
C54	0.79384 (12)	0.5633 (4)	0.45111 (14)	0.0521 (12)
H54	0.7931	0.4946	0.4399	0.063*
C55	0.81460 (12)	0.5807 (4)	0.48903 (15)	0.0600 (13)
H55	0.8277	0.5241	0.5031	0.072*
C56	0.81561 (13)	0.6814 (5)	0.50539 (14)	0.0586 (14)
C57	0.79760 (14)	0.7657 (4)	0.48500 (16)	0.0646 (14)
H57	0.7993	0.8345	0.4962	0.078*
C58	0.77666 (12)	0.7485 (3)	0.44732 (14)	0.0527 (12)
H58	0.7640	0.8062	0.4335	0.063*
C59	0.64382 (13)	0.6103 (4)	0.22842 (13)	0.0500 (12)
C60	0.61853 (15)	0.5403 (4)	0.20475 (15)	0.0730 (16)
C61	0.58138 (18)	0.5715 (6)	0.18808 (18)	0.110 (2)
H61	0.5652	0.5238	0.1723	0.132*
C62	0.56846 (19)	0.6740 (8)	0.1950 (2)	0.134 (3)
H62	0.5430	0.6946	0.1842	0.160*
C63	0.59192 (18)	0.7468 (5)	0.2173 (2)	0.104 (2)
H63	0.5832	0.8171	0.2207	0.124*
C64	0.62870 (13)	0.7132 (4)	0.23456 (14)	0.0638 (14)
C65	0.73278 (10)	0.6111 (3)	0.19656 (12)	0.0363 (10)
C66	0.74258 (10)	0.6947 (3)	0.17164 (13)	0.0414 (11)
H66	0.7439	0.7644	0.1820	0.050*
C67	0.75047 (12)	0.6773 (3)	0.13161 (13)	0.0551 (13)
H67	0.7569	0.7345	0.1152	0.066*
C68	0.74869 (14)	0.5742 (4)	0.11660 (13)	0.0668 (14)
C69	0.73989 (15)	0.4888 (3)	0.14085 (15)	0.0785 (16)
H69	0.7398	0.4189	0.1307	0.094*
C70	0.73121 (13)	0.5077 (3)	0.18019 (13)	0.0586 (13)
H70	0.7241	0.4503	0.1962	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0563 (8)	0.1194 (12)	0.0859 (12)	−0.0003 (8)	0.0009 (7)	0.0310 (9)
Cl2	0.1116 (11)	0.0767 (9)	0.0573 (10)	−0.0021 (8)	0.0221 (8)	0.0114 (7)
Cl3	0.0819 (9)	0.1316 (13)	0.0675 (11)	−0.0149 (9)	−0.0041 (8)	−0.0398 (9)
Cl4	0.0774 (9)	0.0468 (8)	0.1226 (13)	0.0110 (7)	0.0025 (8)	−0.0113 (8)
Cl5	0.1079 (10)	0.0535 (8)	0.1011 (12)	0.0153 (7)	−0.0460 (9)	−0.0132 (7)
Cl6	0.1125 (11)	0.1367 (13)	0.0650 (11)	0.0273 (10)	0.0462 (9)	0.0242 (9)
Cl7	0.0525 (7)	0.0838 (9)	0.0779 (10)	0.0063 (7)	0.0026 (7)	0.0104 (8)
Cl8	0.1310 (12)	0.0760 (9)	0.0559 (10)	0.0039 (8)	0.0140 (9)	0.0205 (7)
Cl9	0.1090 (11)	0.1651 (15)	0.0480 (10)	−0.0409 (10)	−0.0084 (9)	−0.0203 (9)
Cl10	0.1105 (11)	0.0966 (12)	0.0873 (12)	−0.0380 (9)	−0.0127 (9)	−0.0175 (9)
Cl11	0.0690 (8)	0.0616 (9)	0.0994 (12)	0.0129 (7)	0.0236 (8)	−0.0009 (7)
Cl12	0.276 (2)	0.0876 (11)	0.0553 (11)	−0.0265 (12)	0.0745 (13)	−0.0123 (8)
N1	0.059 (3)	0.049 (3)	0.041 (3)	−0.009 (2)	0.009 (2)	0.0042 (19)
N2	0.045 (2)	0.045 (2)	0.044 (3)	−0.0047 (18)	0.002 (2)	0.0062 (19)
N3	0.045 (2)	0.043 (2)	0.037 (2)	0.0048 (19)	0.0101 (18)	0.0065 (17)
N4	0.054 (3)	0.046 (2)	0.040 (3)	−0.0125 (19)	0.005 (2)	0.0028 (18)
O1	0.080 (2)	0.0351 (19)	0.050 (2)	0.0067 (16)	0.0028 (16)	0.0012 (15)
O2	0.0502 (18)	0.0417 (19)	0.048 (2)	0.0021 (15)	0.0076 (15)	0.0044 (14)
O3	0.0496 (18)	0.0444 (18)	0.046 (2)	−0.0105 (15)	−0.0064 (15)	0.0113 (14)
O4	0.069 (2)	0.0333 (18)	0.049 (2)	0.0058 (15)	−0.0005 (16)	−0.0015 (15)
O5	0.0476 (18)	0.0451 (19)	0.038 (2)	0.0133 (14)	0.0122 (15)	0.0020 (13)
O6	0.0560 (19)	0.0347 (18)	0.041 (2)	−0.0034 (15)	0.0028 (16)	0.0040 (13)
C1	0.030 (2)	0.040 (3)	0.045 (3)	−0.004 (2)	0.009 (2)	0.005 (2)
C2	0.038 (3)	0.041 (3)	0.037 (3)	−0.005 (2)	0.005 (2)	0.001 (2)
C3	0.044 (3)	0.069 (3)	0.047 (3)	−0.009 (2)	0.006 (2)	−0.004 (2)
C4	0.037 (3)	0.070 (3)	0.064 (4)	−0.010 (2)	0.006 (3)	−0.004 (3)
C5	0.051 (3)	0.062 (3)	0.052 (4)	0.004 (2)	0.016 (3)	−0.006 (2)
C6	0.049 (3)	0.043 (3)	0.038 (3)	0.006 (2)	0.001 (2)	0.001 (2)
C7	0.040 (3)	0.034 (3)	0.039 (3)	−0.006 (2)	0.005 (2)	0.003 (2)
C8	0.050 (3)	0.049 (3)	0.036 (3)	−0.006 (3)	0.006 (2)	0.001 (2)
C9	0.040 (2)	0.035 (3)	0.044 (3)	0.000 (2)	0.005 (2)	0.004 (2)
C10	0.038 (3)	0.035 (3)	0.041 (3)	0.004 (2)	0.008 (2)	−0.003 (2)
C11	0.044 (3)	0.028 (2)	0.040 (3)	0.002 (2)	0.009 (2)	0.0029 (19)
C12	0.052 (3)	0.053 (3)	0.040 (3)	−0.016 (3)	0.014 (3)	−0.010 (2)
C13	0.048 (3)	0.085 (4)	0.059 (4)	−0.013 (3)	0.009 (3)	0.001 (3)
C14	0.052 (4)	0.112 (5)	0.081 (5)	−0.014 (3)	0.011 (3)	−0.003 (4)
C15	0.064 (4)	0.131 (6)	0.075 (5)	−0.035 (4)	0.026 (4)	−0.017 (4)
C16	0.087 (4)	0.088 (4)	0.054 (4)	−0.043 (4)	0.016 (4)	−0.006 (3)
C17	0.062 (3)	0.068 (3)	0.048 (4)	−0.027 (3)	0.019 (3)	−0.015 (3)
C18	0.045 (3)	0.032 (3)	0.043 (3)	−0.001 (2)	0.009 (2)	−0.003 (2)
C19	0.073 (3)	0.046 (3)	0.066 (4)	0.004 (3)	−0.014 (3)	0.006 (3)
C20	0.093 (4)	0.045 (3)	0.091 (5)	0.000 (3)	−0.014 (4)	−0.021 (3)
C21	0.047 (3)	0.077 (4)	0.041 (3)	−0.007 (3)	0.002 (2)	−0.011 (3)
C22	0.076 (3)	0.059 (4)	0.047 (4)	−0.002 (3)	−0.008 (3)	0.007 (3)
C23	0.084 (3)	0.037 (3)	0.052 (4)	−0.002 (3)	−0.006 (3)	−0.003 (3)
C24	0.033 (2)	0.043 (3)	0.052 (3)	0.006 (2)	0.008 (2)	0.007 (2)
C25	0.046 (3)	0.042 (3)	0.071 (4)	0.007 (2)	0.006 (3)	0.000 (2)
C26	0.058 (3)	0.056 (4)	0.101 (5)	0.021 (3)	0.002 (3)	0.018 (3)
C27	0.065 (4)	0.088 (5)	0.102 (5)	0.032 (3)	−0.022 (3)	0.007 (4)
C28	0.064 (3)	0.075 (4)	0.087 (5)	0.020 (3)	−0.027 (3)	−0.010 (3)
C29	0.052 (3)	0.049 (3)	0.065 (4)	0.015 (2)	−0.007 (3)	0.004 (3)
C30	0.034 (2)	0.040 (3)	0.044 (3)	0.006 (2)	0.002 (2)	0.010 (2)
C31	0.048 (3)	0.047 (3)	0.049 (3)	−0.001 (2)	0.014 (2)	0.009 (2)
C32	0.054 (3)	0.061 (3)	0.057 (4)	0.003 (3)	0.013 (3)	−0.001 (3)
C33	0.055 (3)	0.078 (4)	0.050 (4)	0.022 (3)	0.020 (3)	0.016 (3)
C34	0.061 (3)	0.063 (4)	0.080 (4)	0.005 (3)	0.027 (3)	0.030 (3)
C35	0.057 (3)	0.043 (3)	0.061 (4)	−0.001 (2)	0.015 (3)	0.010 (2)
C36	0.031 (2)	0.040 (3)	0.034 (3)	−0.008 (2)	0.011 (2)	0.004 (2)
C37	0.033 (2)	0.041 (3)	0.031 (3)	0.002 (2)	0.006 (2)	−0.0001 (19)
C38	0.038 (3)	0.070 (3)	0.041 (3)	−0.006 (2)	0.005 (2)	0.000 (2)
C39	0.042 (3)	0.102 (4)	0.057 (4)	−0.002 (3)	0.006 (3)	0.001 (3)
C40	0.043 (3)	0.094 (4)	0.045 (4)	0.005 (3)	0.016 (3)	−0.001 (3)
C41	0.057 (3)	0.060 (3)	0.043 (3)	0.019 (3)	0.010 (2)	0.000 (2)
C42	0.040 (3)	0.036 (3)	0.032 (3)	0.003 (2)	0.010 (2)	0.000 (2)
C43	0.036 (3)	0.043 (3)	0.031 (3)	0.006 (2)	0.009 (2)	−0.003 (2)
C44	0.038 (2)	0.038 (3)	0.034 (3)	0.002 (2)	0.005 (2)	−0.001 (2)
C45	0.045 (3)	0.043 (3)	0.032 (3)	−0.007 (2)	0.006 (2)	−0.001 (2)
C46	0.043 (3)	0.029 (2)	0.031 (3)	0.000 (2)	0.008 (2)	0.0009 (19)
C47	0.057 (3)	0.038 (3)	0.041 (3)	−0.008 (2)	0.013 (3)	−0.006 (2)
C48	0.053 (3)	0.053 (3)	0.067 (4)	−0.015 (3)	0.021 (3)	−0.009 (3)
C49	0.069 (4)	0.079 (4)	0.118 (6)	−0.005 (3)	0.035 (4)	0.003 (4)
C50	0.094 (5)	0.087 (5)	0.138 (7)	−0.016 (4)	0.070 (5)	−0.002 (4)
C51	0.118 (5)	0.059 (4)	0.081 (5)	−0.025 (4)	0.060 (4)	0.002 (3)
C52	0.087 (4)	0.042 (3)	0.054 (4)	−0.005 (3)	0.018 (3)	0.000 (2)
C53	0.038 (3)	0.050 (3)	0.031 (3)	−0.005 (2)	0.010 (2)	−0.004 (2)
C54	0.057 (3)	0.057 (3)	0.043 (3)	0.006 (3)	0.004 (3)	−0.005 (3)
C55	0.056 (3)	0.081 (4)	0.042 (4)	0.003 (3)	−0.001 (3)	0.001 (3)
C56	0.057 (3)	0.087 (4)	0.033 (3)	−0.020 (3)	0.009 (3)	−0.013 (3)
C57	0.082 (4)	0.066 (4)	0.048 (4)	−0.025 (3)	0.019 (3)	−0.024 (3)
C58	0.066 (3)	0.049 (3)	0.045 (4)	−0.010 (2)	0.015 (3)	−0.007 (2)
C59	0.041 (3)	0.068 (4)	0.043 (3)	−0.001 (3)	0.014 (2)	0.009 (2)
C60	0.049 (3)	0.108 (5)	0.061 (4)	−0.019 (3)	−0.002 (3)	−0.003 (3)
C61	0.063 (5)	0.185 (8)	0.078 (5)	−0.018 (5)	−0.014 (4)	−0.017 (5)
C62	0.062 (5)	0.228 (10)	0.106 (7)	0.027 (6)	−0.019 (4)	−0.013 (6)
C63	0.068 (4)	0.145 (6)	0.097 (6)	0.047 (4)	0.004 (4)	−0.004 (4)
C64	0.042 (3)	0.099 (4)	0.051 (4)	0.007 (3)	0.009 (3)	0.008 (3)
C65	0.038 (2)	0.035 (3)	0.036 (3)	−0.007 (2)	0.007 (2)	0.005 (2)
C66	0.050 (3)	0.036 (3)	0.040 (3)	−0.004 (2)	0.010 (2)	0.002 (2)
C67	0.089 (4)	0.039 (3)	0.041 (3)	−0.006 (2)	0.024 (3)	0.012 (2)
C68	0.117 (4)	0.053 (3)	0.034 (3)	−0.012 (3)	0.026 (3)	0.000 (2)
C69	0.145 (5)	0.040 (3)	0.056 (4)	−0.016 (3)	0.043 (4)	−0.007 (3)
C70	0.102 (4)	0.036 (3)	0.042 (3)	−0.018 (3)	0.029 (3)	0.007 (2)

Geometric parameters (Å, º) top

Cl1—C13	1.738 (5)	C27—H27	0.9300
Cl2—C17	1.729 (5)	C28—C29	1.377 (6)
Cl3—C21	1.741 (4)	C28—H28	0.9300
Cl4—C25	1.734 (4)	C30—C35	1.380 (5)
Cl5—C29	1.723 (4)	C30—C31	1.385 (5)
Cl6—C33	1.743 (4)	C31—C32	1.382 (5)
Cl7—C48	1.721 (5)	C31—H31	0.9300
Cl8—C52	1.739 (5)	C32—C33	1.367 (5)
Cl9—C56	1.737 (5)	C32—H32	0.9300
Cl10—C60	1.719 (5)	C33—C34	1.376 (6)
Cl11—C64	1.732 (5)	C34—C35	1.379 (6)
Cl12—C68	1.734 (4)	C34—H34	0.9300
N1—C8	1.280 (4)	C35—H35	0.9300
N1—O2	1.423 (4)	C36—C37	1.545 (5)
N2—C10	1.271 (4)	C36—C42	1.548 (5)
N2—O3	1.400 (4)	C37—C38	1.534 (5)
N3—C43	1.274 (4)	C37—C44	1.545 (5)
N3—O5	1.418 (3)	C38—C39	1.527 (5)
N4—C45	1.273 (4)	C38—H38A	0.9700
N4—O6	1.409 (4)	C38—H38B	0.9700
O1—C1	1.206 (4)	C39—C40	1.524 (5)
O2—C2	1.445 (4)	C39—H39A	0.9700
O3—C7	1.467 (4)	C39—H39B	0.9700
O4—C36	1.205 (4)	C40—C41	1.538 (5)
O5—C37	1.443 (4)	C40—H40A	0.9700
O6—C42	1.463 (4)	C40—H40B	0.9700
C1—C2	1.539 (5)	C41—C42	1.519 (5)
C1—C7	1.552 (5)	C41—H41A	0.9700
C2—C3	1.526 (5)	C41—H41B	0.9700
C2—C9	1.538 (5)	C42—C46	1.539 (5)
C3—C4	1.528 (5)	C43—C47	1.477 (5)
C3—H3A	0.9700	C43—C44	1.526 (5)
C3—H3B	0.9700	C44—C53	1.511 (5)
C4—C5	1.515 (5)	C44—H44	0.9800
C4—H4A	0.9700	C45—C59	1.480 (5)
C4—H4B	0.9700	C45—C46	1.509 (5)
C5—C6	1.531 (5)	C46—C65	1.512 (5)
C5—H5A	0.9700	C46—H46	0.9800
C5—H5B	0.9700	C47—C52	1.386 (5)
C6—C7	1.521 (5)	C47—C48	1.391 (5)
C6—H6A	0.9700	C48—C49	1.389 (6)
C6—H6B	0.9700	C49—C50	1.356 (7)
C7—C11	1.547 (5)	C49—H49	0.9300
C8—C12	1.474 (5)	C50—C51	1.367 (7)
C8—C9	1.515 (5)	C50—H50	0.9300
C9—C18	1.508 (5)	C51—C52	1.393 (6)
C9—H9	0.9800	C51—H51	0.9300
C10—C24	1.476 (5)	C53—C54	1.384 (5)
C10—C11	1.518 (5)	C53—C58	1.387 (5)
C11—C30	1.507 (5)	C54—C55	1.391 (5)
C11—H11	0.9800	C54—H54	0.9300
C12—C17	1.395 (6)	C55—C56	1.361 (6)
C12—C13	1.395 (5)	C55—H55	0.9300
C13—C14	1.372 (6)	C56—C57	1.356 (6)
C14—C15	1.385 (7)	C57—C58	1.386 (6)
C14—H14	0.9300	C57—H57	0.9300
C15—C16	1.368 (6)	C58—H58	0.9300
C15—H15	0.9300	C59—C64	1.396 (6)
C16—C17	1.372 (6)	C59—C60	1.401 (6)
C16—H16	0.9300	C60—C61	1.371 (6)
C18—C19	1.367 (5)	C61—C62	1.370 (8)
C18—C23	1.372 (5)	C61—H61	0.9300
C19—C20	1.394 (6)	C62—C63	1.369 (8)
C19—H19	0.9300	C62—H62	0.9300
C20—C21	1.350 (6)	C63—C64	1.376 (6)
C20—H20	0.9300	C63—H63	0.9300
C21—C22	1.347 (5)	C65—C66	1.381 (5)
C22—C23	1.372 (5)	C65—C70	1.392 (5)
C22—H22	0.9300	C66—C67	1.385 (5)
C23—H23	0.9300	C66—H66	0.9300
C24—C25	1.385 (5)	C67—C68	1.372 (5)
C24—C29	1.398 (5)	C67—H67	0.9300
C25—C26	1.382 (6)	C68—C69	1.375 (5)
C26—C27	1.370 (6)	C69—C70	1.374 (5)
C26—H26	0.9300	C69—H69	0.9300
C27—C28	1.367 (6)	C70—H70	0.9300

C8—N1—O2	109.2 (3)	C35—C34—H34	120.6
C10—N2—O3	109.9 (3)	C34—C35—C30	121.6 (4)
C43—N3—O5	108.9 (3)	C34—C35—H35	119.2
C45—N4—O6	109.0 (3)	C30—C35—H35	119.2
N1—O2—C2	107.2 (3)	O4—C36—C37	118.2 (3)
N2—O3—C7	109.5 (3)	O4—C36—C42	121.5 (4)
N3—O5—C37	107.7 (2)	C37—C36—C42	119.8 (3)
N4—O6—C42	108.7 (3)	O5—C37—C38	109.1 (3)
O1—C1—C2	118.3 (4)	O5—C37—C36	112.4 (3)
O1—C1—C7	120.8 (4)	C38—C37—C36	106.1 (3)
C2—C1—C7	120.7 (4)	O5—C37—C44	103.3 (3)
O2—C2—C3	108.9 (3)	C38—C37—C44	116.4 (3)
O2—C2—C9	103.9 (3)	C36—C37—C44	109.7 (3)
C3—C2—C9	117.4 (3)	C39—C38—C37	114.9 (3)
O2—C2—C1	112.3 (3)	C39—C38—H38A	108.5
C3—C2—C1	105.8 (3)	C37—C38—H38A	108.5
C9—C2—C1	108.7 (3)	C39—C38—H38B	108.5
C2—C3—C4	115.0 (3)	C37—C38—H38B	108.5
C2—C3—H3A	108.5	H38A—C38—H38B	107.5
C4—C3—H3A	108.5	C40—C39—C38	117.9 (3)
C2—C3—H3B	108.5	C40—C39—H39A	107.8
C4—C3—H3B	108.5	C38—C39—H39A	107.8
H3A—C3—H3B	107.5	C40—C39—H39B	107.8
C5—C4—C3	119.3 (3)	C38—C39—H39B	107.8
C5—C4—H4A	107.5	H39A—C39—H39B	107.2
C3—C4—H4A	107.5	C39—C40—C41	113.9 (4)
C5—C4—H4B	107.5	C39—C40—H40A	108.8
C3—C4—H4B	107.5	C41—C40—H40A	108.8
H4A—C4—H4B	107.0	C39—C40—H40B	108.8
C4—C5—C6	115.4 (3)	C41—C40—H40B	108.8
C4—C5—H5A	108.4	H40A—C40—H40B	107.7
C6—C5—H5A	108.4	C42—C41—C40	115.3 (3)
C4—C5—H5B	108.4	C42—C41—H41A	108.5
C6—C5—H5B	108.4	C40—C41—H41A	108.5
H5A—C5—H5B	107.5	C42—C41—H41B	108.5
C7—C6—C5	114.3 (3)	C40—C41—H41B	108.5
C7—C6—H6A	108.7	H41A—C41—H41B	107.5
C5—C6—H6A	108.7	O6—C42—C41	107.7 (3)
C7—C6—H6B	108.7	O6—C42—C46	103.5 (3)
C5—C6—H6B	108.7	C41—C42—C46	118.6 (3)
H6A—C6—H6B	107.6	O6—C42—C36	107.3 (3)
O3—C7—C6	107.7 (3)	C41—C42—C36	109.4 (3)
O3—C7—C11	104.8 (3)	C46—C42—C36	109.7 (3)
C6—C7—C11	118.2 (3)	N3—C43—C47	120.5 (4)
O3—C7—C1	105.5 (3)	N3—C43—C44	113.6 (3)
C6—C7—C1	110.7 (3)	C47—C43—C44	125.8 (3)
C11—C7—C1	109.0 (3)	C53—C44—C43	110.8 (3)
N1—C8—C12	119.4 (4)	C53—C44—C37	116.8 (3)
N1—C8—C9	113.3 (4)	C43—C44—C37	97.4 (3)
C12—C8—C9	127.3 (4)	C53—C44—H44	110.4
C18—C9—C8	112.9 (3)	C43—C44—H44	110.4
C18—C9—C2	117.5 (3)	C37—C44—H44	110.4
C8—C9—C2	98.1 (3)	N4—C45—C59	118.8 (4)
C18—C9—H9	109.2	N4—C45—C46	114.5 (4)
C8—C9—H9	109.2	C59—C45—C46	126.4 (4)
C2—C9—H9	109.2	C45—C46—C65	110.4 (3)
N2—C10—C24	120.4 (4)	C45—C46—C42	98.9 (3)
N2—C10—C11	114.9 (4)	C65—C46—C42	117.3 (3)
C24—C10—C11	124.7 (4)	C45—C46—H46	109.9
C30—C11—C10	113.1 (3)	C65—C46—H46	109.9
C30—C11—C7	119.3 (3)	C42—C46—H46	109.9
C10—C11—C7	99.4 (3)	C52—C47—C48	116.1 (4)
C30—C11—H11	108.1	C52—C47—C43	125.0 (4)
C10—C11—H11	108.1	C48—C47—C43	118.9 (4)
C7—C11—H11	108.1	C49—C48—C47	122.3 (5)
C17—C12—C13	116.6 (4)	C49—C48—Cl7	117.1 (4)
C17—C12—C8	122.9 (4)	C47—C48—Cl7	120.6 (4)
C13—C12—C8	120.5 (4)	C50—C49—C48	119.2 (5)
C14—C13—C12	122.1 (5)	C50—C49—H49	120.4
C14—C13—Cl1	118.2 (4)	C48—C49—H49	120.4
C12—C13—Cl1	119.5 (4)	C49—C50—C51	121.2 (6)
C13—C14—C15	119.4 (5)	C49—C50—H50	119.4
C13—C14—H14	120.3	C51—C50—H50	119.4
C15—C14—H14	120.3	C50—C51—C52	118.9 (5)
C16—C15—C14	120.1 (5)	C50—C51—H51	120.6
C16—C15—H15	120.0	C52—C51—H51	120.6
C14—C15—H15	120.0	C47—C52—C51	122.3 (5)
C15—C16—C17	120.1 (5)	C47—C52—Cl8	120.5 (4)
C15—C16—H16	120.0	C51—C52—Cl8	117.2 (4)
C17—C16—H16	120.0	C54—C53—C58	117.7 (4)
C16—C17—C12	121.8 (5)	C54—C53—C44	121.5 (4)
C16—C17—Cl2	116.8 (4)	C58—C53—C44	120.7 (4)
C12—C17—Cl2	121.4 (4)	C53—C54—C55	120.9 (4)
C19—C18—C23	116.5 (4)	C53—C54—H54	119.5
C19—C18—C9	120.6 (4)	C55—C54—H54	119.5
C23—C18—C9	122.9 (4)	C56—C55—C54	119.4 (5)
C18—C19—C20	121.7 (4)	C56—C55—H55	120.3
C18—C19—H19	119.2	C54—C55—H55	120.3
C20—C19—H19	119.2	C57—C56—C55	121.3 (5)
C21—C20—C19	119.4 (4)	C57—C56—Cl9	119.9 (4)
C21—C20—H20	120.3	C55—C56—Cl9	118.8 (4)
C19—C20—H20	120.3	C56—C57—C58	119.4 (4)
C22—C21—C20	120.3 (5)	C56—C57—H57	120.3
C22—C21—Cl3	120.7 (4)	C58—C57—H57	120.3
C20—C21—Cl3	119.0 (4)	C57—C58—C53	121.2 (4)
C21—C22—C23	119.9 (4)	C57—C58—H58	119.4
C21—C22—H22	120.1	C53—C58—H58	119.4
C23—C22—H22	120.1	C64—C59—C60	116.1 (4)
C22—C23—C18	122.2 (4)	C64—C59—C45	120.2 (4)
C22—C23—H23	118.9	C60—C59—C45	123.7 (4)
C18—C23—H23	118.9	C61—C60—C59	122.0 (5)
C25—C24—C29	115.8 (4)	C61—C60—Cl10	117.1 (5)
C25—C24—C10	122.0 (4)	C59—C60—Cl10	120.9 (4)
C29—C24—C10	122.2 (4)	C62—C61—C60	119.0 (7)
C26—C25—C24	122.5 (4)	C62—C61—H61	120.5
C26—C25—Cl4	117.8 (4)	C60—C61—H61	120.5
C24—C25—Cl4	119.6 (4)	C63—C62—C61	121.9 (7)
C27—C26—C25	119.5 (5)	C63—C62—H62	119.0
C27—C26—H26	120.3	C61—C62—H62	119.0
C25—C26—H26	120.3	C62—C63—C64	118.1 (6)
C28—C27—C26	120.1 (5)	C62—C63—H63	120.9
C28—C27—H27	120.0	C64—C63—H63	120.9
C26—C27—H27	120.0	C63—C64—C59	122.8 (5)
C27—C28—C29	119.9 (5)	C63—C64—Cl11	116.3 (5)
C27—C28—H28	120.1	C59—C64—Cl11	120.9 (4)
C29—C28—H28	120.1	C66—C65—C70	117.8 (4)
C28—C29—C24	122.1 (4)	C66—C65—C46	121.4 (4)
C28—C29—Cl5	116.9 (4)	C70—C65—C46	120.8 (3)
C24—C29—Cl5	120.9 (3)	C65—C66—C67	121.6 (4)
C35—C30—C31	118.0 (4)	C65—C66—H66	119.2
C35—C30—C11	120.0 (4)	C67—C66—H66	119.2
C31—C30—C11	122.0 (4)	C68—C67—C66	118.9 (4)
C32—C31—C30	121.1 (4)	C68—C67—H67	120.6
C32—C31—H31	119.5	C66—C67—H67	120.6
C30—C31—H31	119.5	C67—C68—C69	121.0 (4)
C33—C32—C31	119.4 (4)	C67—C68—Cl12	119.2 (3)
C33—C32—H32	120.3	C69—C68—Cl12	119.8 (4)
C31—C32—H32	120.3	C70—C69—C68	119.4 (4)
C32—C33—C34	121.0 (5)	C70—C69—H69	120.3
C32—C33—Cl6	120.0 (4)	C68—C69—H69	120.3
C34—C33—Cl6	119.1 (4)	C69—C70—C65	121.3 (4)
C33—C34—C35	118.8 (4)	C69—C70—H70	119.4
C33—C34—H34	120.6	C65—C70—H70	119.4

C8—N1—O2—C2	−16.0 (4)	C31—C30—C35—C34	1.7 (6)
C10—N2—O3—C7	8.4 (4)	C11—C30—C35—C34	−177.0 (4)
C43—N3—O5—C37	−17.2 (4)	N3—O5—C37—C38	153.4 (3)
C45—N4—O6—C42	12.8 (4)	N3—O5—C37—C36	−89.3 (3)
N1—O2—C2—C3	153.4 (3)	N3—O5—C37—C44	29.0 (3)
N1—O2—C2—C9	27.5 (3)	O4—C36—C37—O5	166.4 (3)
N1—O2—C2—C1	−89.7 (3)	C42—C36—C37—O5	−22.0 (4)
O1—C1—C2—O2	161.6 (3)	O4—C36—C37—C38	−74.5 (4)
C7—C1—C2—O2	−23.2 (5)	C42—C36—C37—C38	97.2 (4)
O1—C1—C2—C3	−79.7 (4)	O4—C36—C37—C44	52.0 (4)
C7—C1—C2—C3	95.5 (4)	C42—C36—C37—C44	−136.3 (3)
O1—C1—C2—C9	47.3 (4)	O5—C37—C38—C39	55.4 (4)
C7—C1—C2—C9	−137.6 (3)	C36—C37—C38—C39	−65.8 (4)
O2—C2—C3—C4	53.9 (4)	C44—C37—C38—C39	171.8 (3)
C9—C2—C3—C4	171.4 (4)	C37—C38—C39—C40	53.1 (5)
C1—C2—C3—C4	−67.1 (4)	C38—C39—C40—C41	−72.9 (5)
C2—C3—C4—C5	51.4 (5)	C39—C40—C41—C42	86.6 (4)
C3—C4—C5—C6	−68.8 (5)	N4—O6—C42—C41	−148.7 (3)
C4—C5—C6—C7	85.5 (4)	N4—O6—C42—C46	−22.3 (3)
N2—O3—C7—C6	−139.0 (3)	N4—O6—C42—C36	93.6 (3)
N2—O3—C7—C11	−12.4 (4)	C40—C41—C42—O6	−149.2 (3)
N2—O3—C7—C1	102.7 (3)	C40—C41—C42—C46	93.8 (4)
C5—C6—C7—O3	−152.2 (3)	C40—C41—C42—C36	−32.9 (5)
C5—C6—C7—C11	89.4 (4)	O4—C36—C42—O6	−125.6 (4)
C5—C6—C7—C1	−37.3 (5)	C37—C36—C42—O6	63.0 (4)
O1—C1—C7—O3	−116.5 (4)	O4—C36—C42—C41	117.8 (4)
C2—C1—C7—O3	68.4 (4)	C37—C36—C42—C41	−53.6 (4)
O1—C1—C7—C6	127.2 (4)	O4—C36—C42—C46	−13.9 (5)
C2—C1—C7—C6	−47.9 (4)	C37—C36—C42—C46	174.8 (3)
O1—C1—C7—C11	−4.5 (5)	O5—N3—C43—C47	179.1 (3)
C2—C1—C7—C11	−179.5 (3)	O5—N3—C43—C44	−2.8 (4)
O2—N1—C8—C12	177.5 (3)	N3—C43—C44—C53	−102.7 (4)
O2—N1—C8—C9	−3.3 (5)	C47—C43—C44—C53	75.2 (5)
N1—C8—C9—C18	−105.2 (4)	N3—C43—C44—C37	19.6 (4)
C12—C8—C9—C18	74.0 (5)	C47—C43—C44—C37	−162.4 (4)
N1—C8—C9—C2	19.3 (4)	O5—C37—C44—C53	90.2 (4)
C12—C8—C9—C2	−161.5 (4)	C38—C37—C44—C53	−29.4 (5)
O2—C2—C9—C18	94.3 (4)	C36—C37—C44—C53	−149.8 (3)
C3—C2—C9—C18	−26.0 (5)	O5—C37—C44—C43	−27.6 (3)
C1—C2—C9—C18	−146.0 (3)	C38—C37—C44—C43	−147.2 (3)
O2—C2—C9—C8	−26.9 (3)	C36—C37—C44—C43	92.4 (3)
C3—C2—C9—C8	−147.1 (3)	O6—N4—C45—C59	177.0 (3)
C1—C2—C9—C8	92.9 (3)	O6—N4—C45—C46	3.0 (5)
O3—N2—C10—C24	177.9 (3)	N4—C45—C46—C65	107.3 (4)
O3—N2—C10—C11	−0.5 (5)	C59—C45—C46—C65	−66.1 (5)
N2—C10—C11—C30	120.6 (4)	N4—C45—C46—C42	−16.2 (4)
C24—C10—C11—C30	−57.7 (5)	C59—C45—C46—C42	170.4 (4)
N2—C10—C11—C7	−6.9 (4)	O6—C42—C46—C45	21.7 (3)
C24—C10—C11—C7	174.7 (4)	C41—C42—C46—C45	140.8 (3)
O3—C7—C11—C30	−112.4 (4)	C36—C42—C46—C45	−92.5 (3)
C6—C7—C11—C30	7.6 (5)	O6—C42—C46—C65	−96.8 (3)
C1—C7—C11—C30	135.1 (3)	C41—C42—C46—C65	22.4 (5)
O3—C7—C11—C10	10.9 (3)	C36—C42—C46—C65	149.0 (3)
C6—C7—C11—C10	130.9 (3)	N3—C43—C47—C52	64.0 (6)
C1—C7—C11—C10	−101.6 (3)	C44—C43—C47—C52	−113.9 (5)
N1—C8—C12—C17	61.1 (6)	N3—C43—C47—C48	−115.7 (4)
C9—C8—C12—C17	−118.1 (5)	C44—C43—C47—C48	66.4 (5)
N1—C8—C12—C13	−116.9 (5)	C52—C47—C48—C49	1.0 (7)
C9—C8—C12—C13	64.0 (6)	C43—C47—C48—C49	−179.3 (4)
C17—C12—C13—C14	−0.8 (7)	C52—C47—C48—Cl7	−177.7 (3)
C8—C12—C13—C14	177.2 (4)	C43—C47—C48—Cl7	2.0 (5)
C17—C12—C13—Cl1	−176.9 (3)	C47—C48—C49—C50	0.7 (8)
C8—C12—C13—Cl1	1.2 (6)	Cl7—C48—C49—C50	179.4 (5)
C12—C13—C14—C15	0.1 (8)	C48—C49—C50—C51	−1.9 (9)
Cl1—C13—C14—C15	176.2 (4)	C49—C50—C51—C52	1.2 (9)
C13—C14—C15—C16	−0.1 (8)	C48—C47—C52—C51	−1.6 (7)
C14—C15—C16—C17	0.9 (8)	C43—C47—C52—C51	178.7 (4)
C15—C16—C17—C12	−1.7 (7)	C48—C47—C52—Cl8	175.9 (3)
C15—C16—C17—Cl2	178.3 (4)	C43—C47—C52—Cl8	−3.8 (6)
C13—C12—C17—C16	1.6 (6)	C50—C51—C52—C47	0.6 (8)
C8—C12—C17—C16	−176.4 (4)	C50—C51—C52—Cl8	−177.0 (4)
C13—C12—C17—Cl2	−178.4 (3)	C43—C44—C53—C54	40.0 (5)
C8—C12—C17—Cl2	3.6 (6)	C37—C44—C53—C54	−70.3 (5)
C8—C9—C18—C19	−133.4 (4)	C43—C44—C53—C58	−140.1 (4)
C2—C9—C18—C19	113.5 (4)	C37—C44—C53—C58	109.7 (4)
C8—C9—C18—C23	47.2 (5)	C58—C53—C54—C55	1.3 (6)
C2—C9—C18—C23	−65.9 (5)	C44—C53—C54—C55	−178.7 (3)
C23—C18—C19—C20	−0.6 (6)	C53—C54—C55—C56	−0.1 (6)
C9—C18—C19—C20	179.9 (4)	C54—C55—C56—C57	−1.7 (7)
C18—C19—C20—C21	2.0 (7)	C54—C55—C56—Cl9	177.3 (3)
C19—C20—C21—C22	−1.8 (7)	C55—C56—C57—C58	2.1 (7)
C19—C20—C21—Cl3	178.4 (3)	Cl9—C56—C57—C58	−176.8 (3)
C20—C21—C22—C23	0.2 (7)	C56—C57—C58—C53	−0.8 (6)
Cl3—C21—C22—C23	−180.0 (3)	C54—C53—C58—C57	−0.9 (6)
C21—C22—C23—C18	1.3 (7)	C44—C53—C58—C57	179.2 (3)
C19—C18—C23—C22	−1.0 (6)	N4—C45—C59—C64	125.1 (4)
C9—C18—C23—C22	178.4 (4)	C46—C45—C59—C64	−61.8 (6)
N2—C10—C24—C25	122.4 (4)	N4—C45—C59—C60	−52.9 (6)
C11—C10—C24—C25	−59.4 (6)	C46—C45—C59—C60	120.2 (5)
N2—C10—C24—C29	−56.7 (6)	C64—C59—C60—C61	1.0 (7)
C11—C10—C24—C29	121.5 (4)	C45—C59—C60—C61	179.0 (5)
C29—C24—C25—C26	−4.2 (6)	C64—C59—C60—Cl10	179.5 (3)
C10—C24—C25—C26	176.7 (4)	C45—C59—C60—Cl10	−2.4 (6)
C29—C24—C25—Cl4	173.4 (3)	C59—C60—C61—C62	−0.4 (9)
C10—C24—C25—Cl4	−5.8 (5)	Cl10—C60—C61—C62	−179.0 (5)
C24—C25—C26—C27	3.1 (7)	C60—C61—C62—C63	1.5 (12)
Cl4—C25—C26—C27	−174.5 (4)	C61—C62—C63—C64	−3.0 (11)
C25—C26—C27—C28	−0.6 (8)	C62—C63—C64—C59	3.6 (9)
C26—C27—C28—C29	−0.6 (8)	C62—C63—C64—Cl11	−175.7 (5)
C27—C28—C29—C24	−0.6 (7)	C60—C59—C64—C63	−2.6 (7)
C27—C28—C29—Cl5	−178.8 (4)	C45—C59—C64—C63	179.3 (5)
C25—C24—C29—C28	2.9 (6)	C60—C59—C64—Cl11	176.7 (3)
C10—C24—C29—C28	−177.9 (4)	C45—C59—C64—Cl11	−1.5 (6)
C25—C24—C29—Cl5	−179.0 (3)	C45—C46—C65—C66	128.1 (4)
C10—C24—C29—Cl5	0.1 (6)	C42—C46—C65—C66	−119.8 (4)
C10—C11—C30—C35	134.5 (4)	C45—C46—C65—C70	−50.7 (5)
C7—C11—C30—C35	−109.2 (4)	C42—C46—C65—C70	61.4 (5)
C10—C11—C30—C31	−44.2 (5)	C70—C65—C66—C67	0.3 (6)
C7—C11—C30—C31	72.1 (5)	C46—C65—C66—C67	−178.6 (4)
C35—C30—C31—C32	−2.6 (6)	C65—C66—C67—C68	−0.4 (6)
C11—C30—C31—C32	176.1 (4)	C66—C67—C68—C69	−1.1 (7)
C30—C31—C32—C33	0.2 (6)	C66—C67—C68—Cl12	−179.9 (3)
C31—C32—C33—C34	3.3 (7)	C67—C68—C69—C70	2.6 (8)
C31—C32—C33—Cl6	−176.1 (3)	Cl12—C68—C69—C70	−178.5 (4)
C32—C33—C34—C35	−4.1 (7)	C68—C69—C70—C65	−2.7 (8)
Cl6—C33—C34—C35	175.3 (3)	C66—C65—C70—C69	1.3 (7)
C33—C34—C35—C30	1.6 (7)	C46—C65—C70—C69	−179.8 (4)

Experimental details

Crystal data
Chemical formula	C₃₅H₂₄Cl₆N₂O₃
M_r	733.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	33.510 (9), 12.419 (5), 32.946 (9)
β (°)	95.152 (8)
V (Å³)	13655 (8)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.835, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	27390, 11983, 5317
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.099, 0.97
No. of reflections	11983
No. of parameters	829
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.36

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

Selected geometric parameters (Å, º) top

N1—O2	1.423 (4)	N3—O5	1.418 (3)
N2—O3	1.400 (4)	N4—O6	1.409 (4)

N2—O3—C7	109.5 (3)	N4—O6—C42	108.7 (3)

N2—O3—C7—C11	−12.4 (4)	N4—O6—C42—C46	−22.3 (3)
O2—N1—C8—C9	−3.3 (5)	O5—N3—C43—C47	179.1 (3)
O3—N2—C10—C24	177.9 (3)	O5—N3—C43—C44	−2.8 (4)
O3—N2—C10—C11	−0.5 (5)	O6—N4—C45—C59	177.0 (3)
N4—O6—C42—C41	−148.7 (3)	O6—N4—C45—C46	3.0 (5)

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