13-Benzyl-4,11-bis-(4-chloro­phenyl)-3,10-bis(2,6-di­chloro­phenyl)-1,8-dioxa-2,9,13-tri­aza­di­spiro­[4.1.4.3]­tetradeca-2,9-dien-6-one chloro­form solvate

Li, X.-F.; Feng, Y.-Q.; Gao, B.; Li, N.

doi:10.1107/S1600536803023791

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13-Benzyl-4,11-bis-(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa-2,9,13-triazadispiro[4.1.4.3]tetradeca-2,9-dien-6-one chloroform solvate

X.-F. Li, Y.-Q. Feng, B. Gao and N. Li

The title compound, C₄₀H₂₇Cl₆N₃O₃·CHCl₃, was synthesized by the intermolecular [3 + 2]-cycloaddition of 2,6-dichlorobenzonitrile oxide and 1-benzyl-3,5-bis(4-chlorobenzylidene)piperidin-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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023791/ya6179sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023791/ya6179Isup2.hkl Contains datablock I

CCDC reference: 227021

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.048
wR factor = 0.132
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....         24
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C36'
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C39'
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       C10'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C9'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C13'
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C41
PLAT301_ALERT_3_C Main Residue  Disorder .........................      22.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  Cl5      =       3.32 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl9    ..  Cl1'     =       3.43 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       4.30 Deg.
              C34' -N1   -C34     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      14.40 Deg.
              C8'  -C7   -C8      1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

13-Benzyl-4,11-bis-(4-chlorophenyl)-3,10-bis(2,6-dichlorophenyl)-1,8-dioxa- 2,9,13-triazadispiro[4.1.4.3]tetradeca-2,9-dien-6-one chloroform solvate top

Crystal data top

C₄₀H₂₇Cl₆N₃O₃·CHCl₃	Z = 2
M_r = 929.71	F(000) = 944
Triclinic, P1	D_x = 1.484 Mg m⁻³
Hall symbol: -P 1	Melting point: 442 K
a = 11.948 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.066 (4) Å	Cell parameters from 866 reflections
c = 15.674 (5) Å	θ = 3.4–25.2°
α = 97.542 (5)°	µ = 0.65 mm⁻¹
β = 92.617 (5)°	T = 293 K
γ = 111.000 (5)°	Block, colorless
V = 2080.8 (11) Å³	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	8424 independent reflections
Radiation source: fine-focus sealed tube	5461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 26.4°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −14→14
T_min = 0.759, T_max = 0.878	k = −13→15
12075 measured reflections	l = −19→17

Refinement top

Refinement on F²	478 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.132	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.40 e Å⁻³
8424 reflections	Δρ_min = −0.58 e Å⁻³
594 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)
Cl3	0.66654 (8)	0.55328 (8)	0.61243 (5)	0.0642 (2)
Cl4	1.23374 (7)	0.68985 (7)	0.01524 (5)	0.0548 (2)
Cl5	1.48079 (8)	0.50086 (10)	0.21368 (6)	0.0751 (3)
Cl6	1.19288 (9)	−0.03384 (8)	0.04080 (8)	0.0798 (3)
N1	0.88600 (19)	0.37197 (19)	0.27215 (13)	0.0384 (5)
N2	0.8709 (2)	0.7340 (2)	0.20323 (15)	0.0473 (6)
N3	1.24964 (18)	0.58513 (19)	0.23367 (13)	0.0366 (5)
O1	0.99680 (17)	0.58268 (18)	0.09635 (12)	0.0469 (5)
O2	0.81865 (16)	0.60701 (17)	0.17853 (11)	0.0437 (5)
O3	1.13487 (14)	0.52445 (16)	0.26130 (10)	0.0363 (4)
C1	0.9839 (2)	0.5396 (2)	0.16139 (15)	0.0310 (5)
C2	0.8915 (2)	0.5543 (2)	0.22228 (15)	0.0346 (6)
C3	0.8112 (2)	0.4292 (2)	0.23562 (17)	0.0392 (6)
H3A	0.7518	0.4344	0.2745	0.047*
H3B	0.7691	0.3822	0.1808	0.047*
C4	0.9617 (2)	0.3430 (2)	0.20919 (17)	0.0381 (6)
H4A	0.9115	0.2929	0.1578	0.046*
H4B	1.0050	0.2983	0.2335	0.046*
C5	1.0510 (2)	0.4576 (2)	0.18486 (15)	0.0312 (5)
C6	0.9502 (2)	0.6472 (2)	0.30475 (15)	0.0344 (6)
H6	1.0338	0.6552	0.3184	0.041*
C7	0.9443 (3)	0.7563 (2)	0.27017 (17)	0.0423 (6)
Cl1	0.8232 (7)	0.9177 (5)	0.3664 (4)	0.0973 (11)	0.81 (2)
Cl2	1.2069 (5)	0.8347 (4)	0.2440 (3)	0.0672 (8)	0.81 (2)
C8	1.0240 (6)	0.8837 (4)	0.3112 (5)	0.0509 (15)	0.81 (2)
C9	0.9760 (7)	0.9583 (5)	0.3590 (6)	0.0684 (18)	0.81 (2)
C10	1.0515 (9)	1.0710 (4)	0.4012 (5)	0.092 (3)	0.81 (2)
H10	1.0194	1.1209	0.4332	0.110*	0.81 (2)
C11	1.1750 (8)	1.1092 (4)	0.3956 (5)	0.097 (3)	0.81 (2)
H11	1.2255	1.1847	0.4239	0.117*	0.81 (2)
C12	1.2230 (7)	1.0347 (5)	0.3478 (5)	0.0755 (19)	0.81 (2)
H12	1.3056	1.0602	0.3441	0.091*	0.81 (2)
C13	1.1475 (6)	0.9219 (4)	0.3056 (4)	0.0513 (14)	0.81 (2)
Cl1'	0.776 (3)	0.889 (3)	0.355 (2)	0.109 (5)	0.19 (2)
Cl2'	1.1934 (18)	0.865 (3)	0.2545 (16)	0.084 (4)	0.19 (2)
C8'	0.9938 (19)	0.8866 (14)	0.315 (2)	0.042 (6)	0.19 (2)
C9'	0.931 (2)	0.9482 (19)	0.360 (2)	0.068 (7)	0.19 (2)
C10'	0.993 (3)	1.0604 (17)	0.4095 (18)	0.100 (9)	0.19 (2)
H10'	0.9516	1.1015	0.4401	0.119*	0.19 (2)
C11'	1.118 (3)	1.1110 (14)	0.4128 (17)	0.093 (11)	0.19 (2)
H11'	1.1600	1.1861	0.4457	0.112*	0.19 (2)
C12'	1.181 (3)	1.0494 (19)	0.367 (2)	0.078 (9)	0.19 (2)
H12'	1.2644	1.0833	0.3693	0.094*	0.19 (2)
C13'	1.1186 (19)	0.9372 (17)	0.318 (2)	0.046 (6)	0.19 (2)
C14	0.8797 (2)	0.6253 (2)	0.38307 (15)	0.0343 (6)
C15	0.7618 (3)	0.6196 (3)	0.38009 (17)	0.0445 (7)
H15	0.7267	0.6325	0.3300	0.053*
C16	0.6954 (3)	0.5955 (3)	0.44930 (17)	0.0464 (7)
H16	0.6158	0.5906	0.4461	0.056*
C17	0.7493 (3)	0.5786 (2)	0.52368 (16)	0.0427 (6)
C18	0.8661 (3)	0.5837 (3)	0.52908 (17)	0.0449 (7)
H18	0.9013	0.5721	0.5796	0.054*
C19	0.9306 (2)	0.6063 (2)	0.45828 (16)	0.0391 (6)
H19	1.0094	0.6087	0.4611	0.047*
C20	1.1334 (2)	0.4433 (2)	0.11474 (15)	0.0310 (5)
H20	1.1061	0.4626	0.0607	0.037*
C21	1.2500 (2)	0.5437 (2)	0.15462 (16)	0.0332 (5)
C22	1.3597 (2)	0.5919 (2)	0.10858 (16)	0.0368 (6)
C23	1.3589 (2)	0.6551 (2)	0.04043 (17)	0.0415 (6)
C24	1.4568 (3)	0.6969 (3)	−0.0064 (2)	0.0535 (8)
H24	1.4529	0.7377	−0.0521	0.064*
C25	1.5600 (3)	0.6771 (3)	0.0158 (2)	0.0581 (8)
H25	1.6258	0.7035	−0.0160	0.070*
C26	1.5671 (3)	0.6190 (3)	0.0843 (2)	0.0565 (8)
H26	1.6380	0.6083	0.1001	0.068*
C27	1.4676 (2)	0.5764 (3)	0.12938 (18)	0.0465 (7)
C28	1.1480 (2)	0.3229 (2)	0.09696 (15)	0.0327 (5)
C29	1.1155 (2)	0.2553 (2)	0.01526 (16)	0.0379 (6)
H29	1.0844	0.2844	−0.0285	0.046*
C30	1.1282 (3)	0.1455 (2)	−0.00268 (19)	0.0456 (7)
H30	1.1067	0.1013	−0.0581	0.055*
C31	1.1728 (3)	0.1025 (2)	0.0624 (2)	0.0479 (7)
C32	1.2050 (3)	0.1668 (3)	0.1445 (2)	0.0531 (8)
H32	1.2345	0.1364	0.1882	0.064*
C33	1.1932 (3)	0.2768 (3)	0.16150 (18)	0.0456 (7)
H33	1.2158	0.3209	0.2169	0.055*
C34	0.815 (2)	0.2715 (17)	0.3179 (13)	0.059 (7)	0.43 (4)
H34A	0.7825	0.3035	0.3665	0.071*	0.43 (4)
H34B	0.8683	0.2348	0.3402	0.071*	0.43 (4)
C35	0.7122 (12)	0.1760 (16)	0.2569 (13)	0.053 (5)	0.43 (4)
C36	0.5949 (13)	0.1697 (15)	0.2390 (14)	0.056 (4)	0.43 (4)
H36	0.5714	0.2313	0.2637	0.067*	0.43 (4)
C37	0.5126 (13)	0.0713 (19)	0.1842 (14)	0.084 (5)	0.43 (4)
H37	0.4341	0.0671	0.1723	0.101*	0.43 (4)
C38	0.548 (2)	−0.0207 (17)	0.1472 (13)	0.095 (6)	0.43 (4)
H38	0.4927	−0.0866	0.1106	0.114*	0.43 (4)
C39	0.665 (3)	−0.0144 (15)	0.1651 (18)	0.093 (5)	0.43 (4)
H39	0.6886	−0.0760	0.1404	0.112*	0.43 (4)
C40	0.7473 (16)	0.0840 (18)	0.2199 (17)	0.084 (5)	0.43 (4)
H40	0.8259	0.0882	0.2318	0.101*	0.43 (4)
C34'	0.8160 (13)	0.2673 (12)	0.3110 (9)	0.047 (4)	0.57 (4)
H34C	0.7813	0.2960	0.3599	0.056*	0.57 (4)
H34D	0.8719	0.2341	0.3338	0.056*	0.57 (4)
C35'	0.7151 (10)	0.1652 (13)	0.2546 (10)	0.054 (4)	0.57 (4)
C36'	0.6041 (14)	0.1778 (13)	0.2567 (13)	0.088 (5)	0.57 (4)
H36'	0.5959	0.2399	0.2947	0.106*	0.57 (4)
C37'	0.5053 (9)	0.0978 (17)	0.2021 (14)	0.087 (4)	0.57 (4)
H37'	0.4310	0.1062	0.2036	0.105*	0.57 (4)
C38'	0.5175 (13)	0.0050 (17)	0.1454 (10)	0.090 (4)	0.57 (4)
H38'	0.4514	−0.0485	0.1089	0.108*	0.57 (4)
C39'	0.6285 (17)	−0.0076 (12)	0.1432 (10)	0.094 (4)	0.57 (4)
H39'	0.6367	−0.0697	0.1053	0.113*	0.57 (4)
C40'	0.7273 (11)	0.0725 (12)	0.1978 (12)	0.066 (3)	0.57 (4)
H40'	0.8016	0.0640	0.1963	0.079*	0.57 (4)
C41	0.4011 (4)	0.7773 (4)	0.4266 (3)	0.1000 (14)
H41	0.3659	0.7034	0.3843	0.120*
Cl7	0.28470 (14)	0.81526 (18)	0.46714 (10)	0.1378 (6)
Cl8	0.48069 (17)	0.74809 (15)	0.51180 (11)	0.1473 (7)
Cl9	0.49127 (15)	0.8886 (2)	0.37495 (14)	0.1783 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl3	0.0668 (5)	0.0824 (6)	0.0400 (4)	0.0201 (4)	0.0188 (4)	0.0144 (4)
Cl4	0.0530 (4)	0.0559 (5)	0.0634 (5)	0.0230 (4)	0.0110 (4)	0.0263 (4)
Cl5	0.0477 (5)	0.1282 (8)	0.0657 (5)	0.0410 (5)	0.0098 (4)	0.0450 (5)
Cl6	0.0813 (7)	0.0468 (5)	0.1203 (8)	0.0359 (5)	0.0054 (6)	0.0103 (5)
N1	0.0352 (12)	0.0419 (13)	0.0351 (11)	0.0084 (10)	0.0084 (9)	0.0102 (10)
N2	0.0607 (16)	0.0527 (15)	0.0385 (13)	0.0318 (13)	0.0066 (11)	0.0093 (11)
N3	0.0292 (11)	0.0437 (12)	0.0347 (12)	0.0109 (10)	0.0024 (9)	0.0061 (10)
O1	0.0530 (12)	0.0649 (13)	0.0379 (10)	0.0341 (10)	0.0138 (9)	0.0213 (9)
O2	0.0409 (11)	0.0575 (12)	0.0382 (10)	0.0262 (9)	−0.0013 (8)	0.0046 (9)
O3	0.0304 (9)	0.0510 (11)	0.0257 (8)	0.0128 (8)	0.0027 (7)	0.0055 (8)
C1	0.0283 (12)	0.0309 (13)	0.0293 (13)	0.0067 (10)	−0.0022 (10)	0.0026 (10)
C2	0.0315 (13)	0.0430 (15)	0.0307 (13)	0.0155 (11)	0.0018 (10)	0.0056 (11)
C3	0.0296 (13)	0.0457 (16)	0.0353 (14)	0.0074 (12)	0.0044 (11)	0.0007 (12)
C4	0.0373 (14)	0.0396 (14)	0.0384 (14)	0.0135 (12)	0.0070 (11)	0.0101 (11)
C5	0.0309 (13)	0.0363 (13)	0.0255 (12)	0.0117 (11)	0.0014 (10)	0.0044 (10)
C6	0.0359 (14)	0.0361 (14)	0.0319 (13)	0.0139 (11)	0.0034 (10)	0.0064 (11)
C7	0.0557 (18)	0.0436 (16)	0.0335 (14)	0.0234 (14)	0.0093 (13)	0.0099 (12)
Cl1	0.119 (3)	0.096 (2)	0.1051 (16)	0.075 (2)	0.026 (2)	0.0061 (14)
Cl2	0.0613 (13)	0.0505 (14)	0.0781 (12)	0.0071 (9)	0.0198 (8)	0.0049 (10)
C8	0.082 (4)	0.044 (3)	0.040 (3)	0.036 (3)	0.008 (4)	0.013 (3)
C9	0.107 (5)	0.059 (3)	0.057 (3)	0.051 (3)	0.015 (4)	0.010 (3)
C10	0.153 (8)	0.043 (4)	0.080 (4)	0.042 (4)	0.014 (5)	−0.007 (3)
C11	0.159 (7)	0.041 (3)	0.075 (4)	0.025 (4)	−0.001 (5)	−0.009 (3)
C12	0.102 (5)	0.045 (3)	0.064 (4)	0.010 (3)	0.000 (3)	0.008 (2)
C13	0.075 (4)	0.032 (2)	0.045 (3)	0.016 (3)	0.009 (3)	0.0072 (19)
Cl1'	0.113 (11)	0.113 (11)	0.136 (11)	0.077 (9)	0.032 (10)	0.032 (8)
Cl2'	0.060 (5)	0.066 (9)	0.122 (10)	0.013 (5)	0.028 (5)	0.022 (7)
C8'	0.037 (9)	0.054 (14)	0.025 (10)	0.006 (9)	−0.002 (7)	0.010 (10)
C9'	0.110 (18)	0.070 (14)	0.054 (14)	0.075 (13)	−0.007 (15)	0.003 (11)
C10'	0.15 (2)	0.081 (16)	0.075 (16)	0.046 (15)	−0.011 (17)	0.028 (13)
C11'	0.13 (2)	0.036 (13)	0.088 (18)	−0.009 (14)	0.017 (17)	0.016 (11)
C12'	0.092 (17)	0.026 (11)	0.085 (18)	−0.009 (12)	−0.006 (14)	−0.003 (11)
C13'	0.055 (12)	0.050 (11)	0.048 (12)	0.040 (10)	0.015 (10)	0.000 (8)
C14	0.0388 (14)	0.0361 (14)	0.0292 (13)	0.0162 (11)	0.0023 (10)	0.0030 (10)
C15	0.0453 (16)	0.0636 (19)	0.0320 (14)	0.0281 (14)	0.0043 (12)	0.0089 (13)
C16	0.0413 (16)	0.0618 (19)	0.0396 (15)	0.0235 (14)	0.0069 (12)	0.0061 (13)
C17	0.0517 (17)	0.0431 (16)	0.0304 (13)	0.0133 (13)	0.0105 (12)	0.0059 (12)
C18	0.0544 (18)	0.0509 (17)	0.0318 (14)	0.0218 (14)	−0.0007 (12)	0.0094 (12)
C19	0.0405 (15)	0.0426 (15)	0.0353 (14)	0.0174 (12)	−0.0003 (11)	0.0047 (12)
C20	0.0304 (13)	0.0349 (13)	0.0281 (12)	0.0118 (11)	0.0033 (10)	0.0071 (10)
C21	0.0331 (13)	0.0358 (14)	0.0318 (13)	0.0134 (11)	0.0025 (10)	0.0073 (11)
C22	0.0325 (13)	0.0377 (14)	0.0339 (13)	0.0073 (11)	0.0042 (10)	0.0004 (11)
C23	0.0390 (15)	0.0366 (15)	0.0424 (15)	0.0058 (12)	0.0049 (12)	0.0062 (12)
C24	0.0499 (18)	0.0481 (17)	0.0537 (18)	0.0037 (14)	0.0144 (14)	0.0155 (14)
C25	0.0383 (17)	0.062 (2)	0.063 (2)	0.0024 (15)	0.0185 (14)	0.0116 (16)
C26	0.0321 (15)	0.071 (2)	0.0601 (19)	0.0125 (15)	0.0057 (13)	0.0082 (17)
C27	0.0336 (15)	0.0601 (19)	0.0423 (15)	0.0129 (13)	0.0028 (12)	0.0092 (14)
C28	0.0297 (13)	0.0365 (13)	0.0330 (13)	0.0124 (11)	0.0053 (10)	0.0076 (11)
C29	0.0374 (14)	0.0395 (15)	0.0363 (14)	0.0133 (12)	0.0016 (11)	0.0071 (11)
C30	0.0461 (16)	0.0403 (16)	0.0477 (16)	0.0157 (13)	0.0009 (13)	−0.0002 (13)
C31	0.0422 (16)	0.0352 (15)	0.070 (2)	0.0163 (13)	0.0112 (14)	0.0126 (14)
C32	0.0610 (19)	0.0592 (19)	0.0554 (19)	0.0355 (16)	0.0079 (15)	0.0255 (15)
C33	0.0519 (17)	0.0556 (18)	0.0362 (15)	0.0270 (14)	0.0021 (12)	0.0100 (13)
C34	0.061 (11)	0.045 (9)	0.061 (10)	−0.003 (8)	0.026 (8)	0.026 (7)
C35	0.068 (10)	0.036 (6)	0.050 (8)	0.008 (6)	0.019 (8)	0.019 (6)
C36	0.029 (6)	0.050 (7)	0.070 (7)	−0.004 (5)	0.012 (5)	−0.001 (5)
C37	0.056 (7)	0.050 (8)	0.106 (9)	−0.017 (5)	0.013 (6)	−0.025 (7)
C38	0.083 (11)	0.056 (8)	0.109 (10)	−0.007 (8)	0.015 (9)	−0.018 (7)
C39	0.082 (11)	0.075 (8)	0.100 (11)	0.010 (7)	0.017 (9)	−0.012 (8)
C40	0.083 (9)	0.062 (8)	0.062 (9)	−0.023 (7)	0.013 (6)	−0.005 (6)
C34'	0.046 (7)	0.068 (8)	0.028 (5)	0.022 (6)	0.008 (4)	0.011 (5)
C35'	0.043 (6)	0.048 (6)	0.062 (7)	0.002 (5)	0.022 (6)	0.016 (6)
C36'	0.063 (8)	0.077 (8)	0.094 (9)	−0.009 (6)	0.002 (6)	0.010 (6)
C37'	0.054 (6)	0.073 (8)	0.124 (10)	0.010 (5)	0.008 (6)	0.012 (7)
C38'	0.062 (6)	0.067 (8)	0.113 (8)	−0.002 (6)	−0.009 (6)	−0.004 (6)
C39'	0.069 (9)	0.074 (6)	0.104 (9)	−0.002 (5)	−0.001 (7)	−0.019 (6)
C40'	0.053 (5)	0.040 (5)	0.086 (8)	0.003 (4)	0.006 (5)	−0.017 (5)
C41	0.094 (3)	0.093 (3)	0.100 (3)	0.026 (3)	−0.012 (3)	0.000 (3)
Cl7	0.1180 (11)	0.2078 (18)	0.1184 (11)	0.0802 (12)	0.0296 (9)	0.0675 (11)
Cl8	0.1649 (15)	0.1452 (13)	0.1411 (13)	0.0932 (12)	−0.0548 (11)	−0.0261 (10)
Cl9	0.0993 (12)	0.217 (2)	0.1862 (18)	0.0059 (12)	0.0347 (11)	0.0665 (16)

Geometric parameters (Å, º) top

Cl3—C17	1.740 (3)	C18—C19	1.381 (4)
Cl4—C23	1.734 (3)	C18—H18	0.9300
Cl5—C27	1.733 (3)	C19—H19	0.9300
Cl6—C31	1.739 (3)	C20—C28	1.515 (3)
N1—C3	1.450 (3)	C20—C21	1.521 (3)
N1—C4	1.460 (3)	C20—H20	0.9800
N1—C34'	1.468 (11)	C21—C22	1.492 (3)
N1—C34	1.500 (13)	C22—C23	1.393 (4)
N2—C7	1.270 (3)	C22—C27	1.398 (4)
N2—O2	1.423 (3)	C23—C24	1.383 (4)
N3—C21	1.275 (3)	C24—C25	1.375 (4)
N3—O3	1.422 (3)	C24—H24	0.9300
O1—C1	1.195 (3)	C25—C26	1.372 (4)
O2—C2	1.445 (3)	C25—H25	0.9300
O3—C5	1.465 (3)	C26—C27	1.382 (4)
C1—C2	1.534 (3)	C26—H26	0.9300
C1—C5	1.548 (3)	C28—C29	1.382 (3)
C2—C3	1.518 (4)	C28—C33	1.392 (3)
C2—C6	1.547 (3)	C29—C30	1.381 (4)
C3—H3A	0.9700	C29—H29	0.9300
C3—H3B	0.9700	C30—C31	1.372 (4)
C4—C5	1.521 (3)	C30—H30	0.9300
C4—H4A	0.9700	C31—C32	1.372 (4)
C4—H4B	0.9700	C32—C33	1.377 (4)
C5—C20	1.542 (3)	C32—H32	0.9300
C6—C7	1.511 (4)	C33—H33	0.9300
C6—C14	1.518 (3)	C34—C35	1.531 (9)
C6—H6	0.9800	C34—H34A	0.9700
C7—C8'	1.521 (8)	C34—H34B	0.9700
C7—C8	1.523 (4)	C35—C36	1.3900
Cl1—C9	1.726 (4)	C35—C40	1.3900
Cl2—C13	1.696 (4)	C36—C37	1.3900
C8—C9	1.3900	C36—H36	0.9300
C8—C13	1.3900	C37—C38	1.3900
C9—C10	1.3900	C37—H37	0.9300
C10—C11	1.3900	C38—C39	1.3900
C10—H10	0.9300	C38—H38	0.9300
C11—C12	1.3900	C39—C40	1.3900
C11—H11	0.9300	C39—H39	0.9300
C12—C13	1.3900	C40—H40	0.9300
C12—H12	0.9300	C34'—C35'	1.519 (7)
Cl1'—C9'	1.724 (8)	C34'—H34C	0.9700
Cl2'—C13'	1.720 (8)	C34'—H34D	0.9700
C8'—C9'	1.3900	C35'—C36'	1.3900
C8'—C13'	1.3900	C35'—C40'	1.3900
C9'—C10'	1.3900	C36'—C37'	1.3900
C10'—C11'	1.3900	C36'—H36'	0.9300
C10'—H10'	0.9300	C37'—C38'	1.3900
C11'—C12'	1.3900	C37'—H37'	0.9300
C11'—H11'	0.9300	C38'—C39'	1.3900
C12'—C13'	1.3900	C38'—H38'	0.9300
C12'—H12'	0.9300	C39'—C40'	1.3900
C14—C15	1.384 (4)	C39'—H39'	0.9300
C14—C19	1.385 (3)	C40'—H40'	0.9300
C15—C16	1.374 (4)	C41—Cl9	1.717 (5)
C15—H15	0.9300	C41—Cl7	1.735 (5)
C16—C17	1.380 (4)	C41—Cl8	1.750 (5)
C16—H16	0.9300	C41—H41	0.9800
C17—C18	1.373 (4)

C3—N1—C4	111.4 (2)	C18—C19—H19	119.5
C3—N1—C34'	112.6 (7)	C14—C19—H19	119.5
C4—N1—C34'	112.2 (9)	C28—C20—C21	112.1 (2)
C3—N1—C34	112.2 (11)	C28—C20—C5	116.9 (2)
C4—N1—C34	115.8 (13)	C21—C20—C5	98.93 (19)
C34'—N1—C34	4.3 (16)	C28—C20—H20	109.5
C7—N2—O2	107.9 (2)	C21—C20—H20	109.5
C21—N3—O3	108.99 (19)	C5—C20—H20	109.5
N2—O2—C2	108.18 (18)	N3—C21—C22	120.5 (2)
N3—O3—C5	108.51 (16)	N3—C21—C20	114.7 (2)
O1—C1—C2	121.4 (2)	C22—C21—C20	124.8 (2)
O1—C1—C5	122.1 (2)	C23—C22—C27	115.9 (2)
C2—C1—C5	116.3 (2)	C23—C22—C21	120.7 (2)
O2—C2—C3	108.5 (2)	C27—C22—C21	123.3 (2)
O2—C2—C1	107.45 (19)	C24—C23—C22	122.7 (3)
C3—C2—C1	107.3 (2)	C24—C23—Cl4	117.7 (2)
O2—C2—C6	103.64 (19)	C22—C23—Cl4	119.5 (2)
C3—C2—C6	116.7 (2)	C25—C24—C23	119.0 (3)
C1—C2—C6	112.8 (2)	C25—C24—H24	120.5
N1—C3—C2	108.5 (2)	C23—C24—H24	120.5
N1—C3—H3A	110.0	C26—C25—C24	120.7 (3)
C2—C3—H3A	110.0	C26—C25—H25	119.6
N1—C3—H3B	110.0	C24—C25—H25	119.6
C2—C3—H3B	110.0	C25—C26—C27	119.3 (3)
H3A—C3—H3B	108.4	C25—C26—H26	120.3
N1—C4—C5	110.3 (2)	C27—C26—H26	120.3
N1—C4—H4A	109.6	C26—C27—C22	122.3 (3)
C5—C4—H4A	109.6	C26—C27—Cl5	117.2 (2)
N1—C4—H4B	109.6	C22—C27—Cl5	120.5 (2)
C5—C4—H4B	109.6	C29—C28—C33	118.1 (2)
H4A—C4—H4B	108.1	C29—C28—C20	120.2 (2)
O3—C5—C4	108.44 (19)	C33—C28—C20	121.7 (2)
O3—C5—C20	104.17 (18)	C30—C29—C28	121.3 (2)
C4—C5—C20	117.2 (2)	C30—C29—H29	119.3
O3—C5—C1	106.00 (18)	C28—C29—H29	119.3
C4—C5—C1	109.6 (2)	C31—C30—C29	119.1 (3)
C20—C5—C1	110.73 (19)	C31—C30—H30	120.5
C7—C6—C14	110.7 (2)	C29—C30—H30	120.5
C7—C6—C2	97.41 (19)	C32—C31—C30	121.1 (3)
C14—C6—C2	114.6 (2)	C32—C31—Cl6	119.0 (2)
C7—C6—H6	111.1	C30—C31—Cl6	119.9 (2)
C14—C6—H6	111.1	C31—C32—C33	119.3 (3)
C2—C6—H6	111.1	C31—C32—H32	120.3
N2—C7—C6	115.3 (2)	C33—C32—H32	120.3
N2—C7—C8'	115.2 (13)	C32—C33—C28	121.0 (3)
C6—C7—C8'	128.2 (14)	C32—C33—H33	119.5
N2—C7—C8	122.7 (4)	C28—C33—H33	119.5
C6—C7—C8	122.0 (4)	N1—C34—C35	111.1 (14)
C8'—C7—C8	14.4 (8)	N1—C34—H34A	109.4
C9—C8—C13	120.0	C35—C34—H34A	109.4
C9—C8—C7	120.8 (3)	N1—C34—H34B	109.4
C13—C8—C7	119.0 (3)	C35—C34—H34B	109.4
C10—C9—C8	120.0	H34A—C34—H34B	108.0
C10—C9—Cl1	117.7 (3)	C36—C35—C40	120.0
C8—C9—Cl1	122.3 (3)	C36—C35—C34	129.0 (17)
C9—C10—C11	120.0	C40—C35—C34	110.9 (17)
C9—C10—H10	120.0	C35—C36—C37	120.0
C11—C10—H10	120.0	C35—C36—H36	120.0
C12—C11—C10	120.0	C37—C36—H36	120.0
C12—C11—H11	120.0	C38—C37—C36	120.0
C10—C11—H11	120.0	C38—C37—H37	120.0
C11—C12—C13	120.0	C36—C37—H37	120.0
C11—C12—H12	120.0	C37—C38—C39	120.0
C13—C12—H12	120.0	C37—C38—H38	120.0
C12—C13—C8	120.0	C39—C38—H38	120.0
C12—C13—Cl2	119.3 (3)	C40—C39—C38	120.0
C8—C13—Cl2	120.6 (3)	C40—C39—H39	120.0
C9'—C8'—C13'	120.0	C38—C39—H39	120.0
C9'—C8'—C7	127.1 (9)	C39—C40—C35	120.0
C13'—C8'—C7	112.1 (9)	C39—C40—H40	120.0
C8'—C9'—C10'	120.0	C35—C40—H40	120.0
C8'—C9'—Cl1'	120.9 (6)	N1—C34'—C35'	118.4 (11)
C10'—C9'—Cl1'	119.1 (6)	N1—C34'—H34C	107.7
C11'—C10'—C9'	120.0	C35'—C34'—H34C	107.7
C11'—C10'—H10'	120.0	N1—C34'—H34D	107.7
C9'—C10'—H10'	120.0	C35'—C34'—H34D	107.7
C12'—C11'—C10'	120.0	H34C—C34'—H34D	107.1
C12'—C11'—H11'	120.0	C36'—C35'—C40'	120.0
C10'—C11'—H11'	120.0	C36'—C35'—C34'	113.2 (13)
C11'—C12'—C13'	120.0	C40'—C35'—C34'	126.4 (13)
C11'—C12'—H12'	120.0	C35'—C36'—C37'	120.0
C13'—C12'—H12'	120.0	C35'—C36'—H36'	120.0
C12'—C13'—C8'	120.0	C37'—C36'—H36'	120.0
C12'—C13'—Cl2'	120.6 (6)	C38'—C37'—C36'	120.0
C8'—C13'—Cl2'	119.3 (7)	C38'—C37'—H37'	120.0
C15—C14—C19	118.4 (2)	C36'—C37'—H37'	120.0
C15—C14—C6	120.9 (2)	C39'—C38'—C37'	120.0
C19—C14—C6	120.7 (2)	C39'—C38'—H38'	120.0
C16—C15—C14	121.6 (2)	C37'—C38'—H38'	120.0
C16—C15—H15	119.2	C38'—C39'—C40'	120.0
C14—C15—H15	119.2	C38'—C39'—H39'	120.0
C15—C16—C17	118.5 (3)	C40'—C39'—H39'	120.0
C15—C16—H16	120.7	C39'—C40'—C35'	120.0
C17—C16—H16	120.7	C39'—C40'—H40'	120.0
C18—C17—C16	121.5 (2)	C35'—C40'—H40'	120.0
C18—C17—Cl3	120.1 (2)	Cl9—C41—Cl7	110.6 (3)
C16—C17—Cl3	118.4 (2)	Cl9—C41—Cl8	112.6 (3)
C17—C18—C19	119.0 (2)	Cl7—C41—Cl8	108.4 (3)
C17—C18—H18	120.5	Cl9—C41—H41	108.3
C19—C18—H18	120.5	Cl7—C41—H41	108.3
C18—C19—C14	121.0 (3)	Cl8—C41—H41	108.3

C7—N2—O2—C2	−15.9 (3)	C7—C8'—C13'—Cl2'	14 (3)
C21—N3—O3—C5	−13.0 (3)	C7—C6—C14—C15	51.5 (3)
N2—O2—C2—C3	151.3 (2)	C2—C6—C14—C15	−57.5 (3)
N2—O2—C2—C1	−93.0 (2)	C7—C6—C14—C19	−130.8 (3)
N2—O2—C2—C6	26.6 (2)	C2—C6—C14—C19	120.2 (3)
O1—C1—C2—O2	9.3 (3)	C19—C14—C15—C16	−0.2 (4)
C5—C1—C2—O2	−165.76 (19)	C6—C14—C15—C16	177.6 (3)
O1—C1—C2—C3	125.8 (3)	C14—C15—C16—C17	1.1 (4)
C5—C1—C2—C3	−49.3 (3)	C15—C16—C17—C18	−1.0 (4)
O1—C1—C2—C6	−104.3 (3)	C15—C16—C17—Cl3	177.8 (2)
C5—C1—C2—C6	80.6 (3)	C16—C17—C18—C19	0.0 (4)
C4—N1—C3—C2	−69.9 (3)	Cl3—C17—C18—C19	−178.7 (2)
C34'—N1—C3—C2	163.0 (7)	C17—C18—C19—C14	0.9 (4)
C34—N1—C3—C2	158.4 (10)	C15—C14—C19—C18	−0.8 (4)
O2—C2—C3—N1	174.74 (19)	C6—C14—C19—C18	−178.6 (2)
C1—C2—C3—N1	58.9 (2)	O3—C5—C20—C28	100.6 (2)
C6—C2—C3—N1	−68.7 (3)	C4—C5—C20—C28	−19.1 (3)
C3—N1—C4—C5	64.6 (3)	C1—C5—C20—C28	−145.9 (2)
C34'—N1—C4—C5	−168.2 (5)	O3—C5—C20—C21	−19.8 (2)
C34—N1—C4—C5	−165.6 (8)	C4—C5—C20—C21	−139.6 (2)
N3—O3—C5—C4	146.61 (19)	C1—C5—C20—C21	93.7 (2)
N3—O3—C5—C20	21.1 (2)	O3—N3—C21—C22	179.7 (2)
N3—O3—C5—C1	−95.8 (2)	O3—N3—C21—C20	−1.4 (3)
N1—C4—C5—O3	66.0 (2)	C28—C20—C21—N3	−110.0 (2)
N1—C4—C5—C20	−176.53 (19)	C5—C20—C21—N3	13.9 (3)
N1—C4—C5—C1	−49.3 (3)	C28—C20—C21—C22	68.8 (3)
O1—C1—C5—O3	113.0 (2)	C5—C20—C21—C22	−167.3 (2)
C2—C1—C5—O3	−72.0 (2)	N3—C21—C22—C23	−113.9 (3)
O1—C1—C5—C4	−130.2 (2)	C20—C21—C22—C23	67.4 (3)
C2—C1—C5—C4	44.9 (3)	N3—C21—C22—C27	66.7 (4)
O1—C1—C5—C20	0.6 (3)	C20—C21—C22—C27	−112.0 (3)
C2—C1—C5—C20	175.65 (19)	C27—C22—C23—C24	2.2 (4)
O2—C2—C6—C7	−25.2 (2)	C21—C22—C23—C24	−177.2 (3)
C3—C2—C6—C7	−144.4 (2)	C27—C22—C23—Cl4	−174.8 (2)
C1—C2—C6—C7	90.7 (2)	C21—C22—C23—Cl4	5.9 (3)
O2—C2—C6—C14	91.7 (2)	C22—C23—C24—C25	−1.0 (4)
C3—C2—C6—C14	−27.5 (3)	Cl4—C23—C24—C25	176.0 (2)
C1—C2—C6—C14	−152.4 (2)	C23—C24—C25—C26	−1.3 (5)
O2—N2—C7—C6	−2.5 (3)	C24—C25—C26—C27	2.2 (5)
O2—N2—C7—C8'	−170.5 (12)	C25—C26—C27—C22	−0.9 (5)
O2—N2—C7—C8	175.4 (4)	C25—C26—C27—Cl5	178.6 (3)
C14—C6—C7—N2	−101.9 (3)	C23—C22—C27—C26	−1.2 (4)
C2—C6—C7—N2	18.0 (3)	C21—C22—C27—C26	178.1 (3)
C14—C6—C7—C8'	64.2 (12)	C23—C22—C27—Cl5	179.3 (2)
C2—C6—C7—C8'	−175.9 (12)	C21—C22—C27—Cl5	−1.4 (4)
C14—C6—C7—C8	80.1 (4)	C21—C20—C28—C29	−126.2 (2)
C2—C6—C7—C8	−160.0 (4)	C5—C20—C28—C29	120.6 (2)
N2—C7—C8—C9	74.5 (5)	C21—C20—C28—C33	54.2 (3)
C6—C7—C8—C9	−107.7 (5)	C5—C20—C28—C33	−59.0 (3)
C8'—C7—C8—C9	12 (7)	C33—C28—C29—C30	−0.6 (4)
N2—C7—C8—C13	−110.1 (5)	C20—C28—C29—C30	179.8 (2)
C6—C7—C8—C13	67.7 (6)	C28—C29—C30—C31	0.7 (4)
C8'—C7—C8—C13	−173 (7)	C29—C30—C31—C32	−0.1 (4)
C13—C8—C9—C10	0.0	C29—C30—C31—Cl6	−178.5 (2)
C7—C8—C9—C10	175.4 (7)	C30—C31—C32—C33	−0.6 (5)
C13—C8—C9—Cl1	178.4 (7)	Cl6—C31—C32—C33	177.8 (2)
C7—C8—C9—Cl1	−6.2 (6)	C31—C32—C33—C28	0.7 (5)
C8—C9—C10—C11	0.0	C29—C28—C33—C32	−0.1 (4)
Cl1—C9—C10—C11	−178.5 (7)	C20—C28—C33—C32	179.5 (3)
C9—C10—C11—C12	0.0	C3—N1—C34—C35	58 (2)
C10—C11—C12—C13	0.0	C4—N1—C34—C35	−72 (2)
C11—C12—C13—C8	0.0	C34'—N1—C34—C35	−38 (21)
C11—C12—C13—Cl2	177.3 (6)	N1—C34—C35—C36	−89 (2)
C9—C8—C13—C12	0.0	N1—C34—C35—C40	94 (2)
C7—C8—C13—C12	−175.4 (7)	C40—C35—C36—C37	0.0
C9—C8—C13—Cl2	−177.2 (6)	C34—C35—C36—C37	−177 (2)
C7—C8—C13—Cl2	7.3 (7)	C35—C36—C37—C38	0.0
N2—C7—C8'—C9'	70 (2)	C36—C37—C38—C39	0.0
C6—C7—C8'—C9'	−96.2 (19)	C37—C38—C39—C40	0.0
C8—C7—C8'—C9'	−166 (8)	C38—C39—C40—C35	0.0
N2—C7—C8'—C13'	−120.4 (15)	C36—C35—C40—C39	0.0
C6—C7—C8'—C13'	74 (2)	C34—C35—C40—C39	177.3 (18)
C8—C7—C8'—C13'	4 (6)	C3—N1—C34'—C35'	57.5 (17)
C13'—C8'—C9'—C10'	0.0	C4—N1—C34'—C35'	−69.1 (16)
C7—C8'—C9'—C10'	169 (3)	C34—N1—C34'—C35'	143 (24)
C13'—C8'—C9'—Cl1'	178 (3)	N1—C34'—C35'—C36'	−91.1 (17)
C7—C8'—C9'—Cl1'	−13 (3)	N1—C34'—C35'—C40'	82 (2)
C8'—C9'—C10'—C11'	0.0	C40'—C35'—C36'—C37'	0.0
Cl1'—C9'—C10'—C11'	−178 (3)	C34'—C35'—C36'—C37'	173.8 (15)
C9'—C10'—C11'—C12'	0.0	C35'—C36'—C37'—C38'	0.0
C10'—C11'—C12'—C13'	0.0	C36'—C37'—C38'—C39'	0.0
C11'—C12'—C13'—C8'	0.0	C37'—C38'—C39'—C40'	0.0
C11'—C12'—C13'—Cl2'	175 (2)	C38'—C39'—C40'—C35'	0.0
C9'—C8'—C13'—C12'	0.0	C36'—C35'—C40'—C39'	0.0
C7—C8'—C13'—C12'	−171 (3)	C34'—C35'—C40'—C39'	−173.0 (17)
C9'—C8'—C13'—Cl2'	−175 (2)

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