10′′-(4-Chlorobenzyl­idene)-5′′-(4-chlorophen­yl)-4′-(2,4-dichlorophenyl)-1′-methyl-2,3,2′′,3′′,7′′,8′′,9′′,10′′-octa­hydro-1H,5′′H,6′′H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-cyclo­hepteno[1,2-d]thia­zolo[3,2-a]pyrimidine-2,3′′-dione

Hu, X.-F.; Feng, Y.-Q.; Liu, X.-G.; Qiao, K.-J.

doi:10.1107/S1600536805011621

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10′′-(4-Chlorobenzylidene)-5′′-(4-chlorophenyl)-4′-(2,4-dichlorophenyl)-1′-methyl-2,3,2′′,3′′,7′′,8′′,9′′,10′′-octahydro-1H,5′′H,6′′H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-cyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidine-2,3′′-dione

X.-F. Hu, Y.-Q. Feng, X.-G. Liu and K.-J. Qiao

The title compound, C₄₁H₃₂Cl₄N₄O₂S, was synthesized by the intermolecular [3 + 2] cycloaddition of azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 5-(4-chloro)phenyl-10-(4-chloro)benzylidene-2-(2,4-dichloro)benzylidene-2,3,6,7,8,9-hexahydro-5H,10H-cyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidin-3-one. In the molecule, the two spiro junctions link a planar 2-oxindole ring, a pyrrolidine ring in an envelope conformation and a 10-(arylmethylene)hexahydrocyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidin-3-one ring. The packing of the molecules in the crystal structure is mainly due to N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011621/hg6161sup1.cif Contains datablocks DS, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011621/hg6161Isup2.hkl Contains datablock I

CCDC reference: 271892

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.049
wR factor = 0.168
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.03 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C35
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C35'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C30'

Alert level C
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.15
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C36
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C39
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C38'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C39'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C39"
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C32'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C21    -   C22    ...       1.35 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.80 Deg.
              C30" -C21  -C30     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       5.10 Deg.
              C30" -C21  -C30'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      22.60 Deg.
              C30  -C21  -C30'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.10 Deg.
              C30  -C31  -C30'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.20 Deg.
              C30  -C31  -C30"    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       6.30 Deg.
              C30' -C31  -C30"    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.20 Deg.
              C32' -C31  -C32     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.20 Deg.
              H31A -C31  -H31B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.20 Deg.
              H31A -C31  -H31C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              H31B -C31  -H31C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.20 Deg.
              C41  -C40  -H41D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.20 Deg.
              C41  -C40  -H41E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.70 Deg.
              C41  -C40' -H41A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.50 Deg.
              C41  -C40' -H41E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.20 Deg.
              H41A -C40' -H41E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.20 Deg.
              C41  -C40" -H41B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.60 Deg.
              C41  -C40" -H41D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.80 Deg.
              H41B -C40" -H41D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.80 Deg.
              C40' -C41  -C40     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.80 Deg.
              C40  -C41  -C40"    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.10 Deg.
              H41A -C41  -H41C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.60 Deg.
              C40" -C41  -H41D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.80 Deg.
              H41B -C41  -H41D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      22.90 Deg.
              C40' -C41  -H41E    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.70 Deg.
              H41C -C41  -H41F    1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.41
           From the CIF: _reflns_number_total               7655
           Count of symmetry unique reflns         4046
           Completeness (_total/calc)            189.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3609
           Fraction of Friedel pairs measured     0.892
           Are heavy atom types Z>Si present        yes

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  39 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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.

1-N-methyl-spiro[2.3']oxindole-spiro[3.2"]5"-(4-chloro)phenyl -10"-(4-chloro)benzylidene-2",3",6",7",8",9"-hexahydro-5H,10H- cyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidin-3"-one-4-(2,4- dichloro)phenyl-pyrrolidine top

Crystal data top

C₄₁H₃₂Cl₄N₄O₂S	D_x = 1.396 Mg m⁻³
M_r = 786.6	Melting point: 214 K
Tetragonal, I4	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I-4	Cell parameters from 2525 reflections
a = 25.035 (2) Å	θ = 2.5–20.9°
c = 11.929 (2) Å	µ = 0.42 mm⁻¹
V = 7476.6 (16) Å³	T = 293 K
Z = 8	Block, colorless
F(000) = 3248	0.40 × 0.36 × 0.24 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7655 independent reflections
Radiation source: fine-focus sealed tube	4391 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 26.4°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −29→31
T_min = 0.826, T_max = 0.905	k = −31→29
21971 measured reflections	l = −14→10

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0888P)² + 0.1414P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.049	(Δ/σ)_max = 0.004
wR(F²) = 0.168	Δρ_max = 0.49 e Å⁻³
S = 1.00	Δρ_min = −0.23 e Å⁻³
7655 reflections	Absolute structure: Flack (1983), 3609 Friedel pairs
562 parameters	Absolute structure parameter: −0.10 (8)
66 restraints

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)
S1	0.87734 (5)	0.13344 (4)	1.01907 (10)	0.0499 (3)
Cl1	0.71898 (7)	0.15396 (8)	1.1140 (2)	0.1322 (9)
Cl2	0.68229 (8)	0.01616 (8)	0.78233 (19)	0.1154 (7)
Cl3	0.61103 (5)	0.32349 (6)	1.16351 (14)	0.0787 (4)
N1	0.88644 (14)	0.23506 (14)	0.9567 (3)	0.0472 (9)
N2	0.85879 (14)	0.21629 (14)	1.1432 (3)	0.0488 (9)
N3	0.87956 (17)	0.06058 (17)	1.3141 (4)	0.0640 (11)
N4	0.99220 (16)	0.07382 (17)	1.1524 (4)	0.0649 (11)
H4	1.0177	0.0601	1.1135	0.078*
O1	0.92356 (14)	0.02172 (14)	1.0872 (3)	0.0677 (9)
O2	0.82943 (14)	0.18224 (14)	1.3074 (3)	0.0657 (9)
C1	0.85993 (17)	0.12016 (18)	1.1656 (4)	0.0493 (11)
C2	0.81117 (19)	0.08106 (19)	1.1861 (5)	0.0599 (13)
H2A	0.7863	0.1006	1.2346	0.072*
C3	0.8340 (2)	0.0363 (2)	1.2579 (5)	0.0732 (16)
H3A	0.8078	0.0239	1.3120	0.088*
H3B	0.8451	0.0064	1.2118	0.088*
C4	0.90755 (18)	0.09250 (18)	1.2305 (4)	0.0516 (11)
C5	0.9403 (2)	0.0578 (2)	1.1460 (4)	0.0575 (12)
C6	0.99917 (19)	0.1155 (2)	1.2301 (4)	0.0581 (12)
C7	0.95037 (19)	0.12851 (19)	1.2783 (4)	0.0542 (12)
C8	0.9490 (2)	0.1661 (2)	1.3623 (5)	0.0672 (14)
H8A	0.9172	0.1743	1.3987	0.081*
C9	0.9969 (2)	0.1920 (3)	1.3919 (5)	0.0820 (17)
H9A	0.9964	0.2184	1.4468	0.098*
C10	1.0438 (2)	0.1790 (3)	1.3411 (6)	0.0878 (19)
H10A	1.0750	0.1964	1.3622	0.105*
C11	1.0458 (2)	0.1403 (3)	1.2588 (6)	0.0844 (18)
H11A	1.0778	0.1314	1.2239	0.101*
C12	0.9130 (3)	0.0236 (3)	1.3768 (5)	0.0877 (18)
H12A	0.9419	0.0428	1.4109	0.132*
H12B	0.9270	−0.0030	1.3269	0.132*
H12C	0.8920	0.0066	1.4340	0.132*
C13	0.77989 (18)	0.06592 (18)	1.0845 (5)	0.0566 (12)
C14	0.7367 (2)	0.0950 (2)	1.0464 (6)	0.0814 (18)
C15	0.7059 (2)	0.0799 (3)	0.9552 (6)	0.0869 (19)
H15A	0.6759	0.0996	0.9352	0.104*
C16	0.7199 (2)	0.0362 (2)	0.8959 (6)	0.0788 (17)
C17	0.7635 (2)	0.0068 (2)	0.9262 (6)	0.0767 (17)
H17A	0.7735	−0.0229	0.8842	0.092*
C18	0.7929 (2)	0.0213 (2)	1.0199 (5)	0.0710 (15)
H18A	0.8223	0.0008	1.0403	0.085*
C19	0.84756 (18)	0.17511 (19)	1.2151 (4)	0.0506 (11)
C20	0.87453 (16)	0.20302 (17)	1.0346 (4)	0.0458 (10)
C21	0.8869 (2)	0.29103 (18)	0.9842 (4)	0.0576 (12)
C22	0.8721 (2)	0.30919 (18)	1.0862 (5)	0.0606 (13)
C23	0.84585 (17)	0.27262 (18)	1.1698 (4)	0.0513 (11)
H23A	0.8599	0.2809	1.2445	0.062*
C24	0.78635 (18)	0.28248 (18)	1.1703 (4)	0.0520 (11)
C25	0.7593 (2)	0.2937 (2)	1.2681 (4)	0.0611 (13)
H25A	0.7774	0.2927	1.3361	0.073*
C26	0.7055 (2)	0.3064 (2)	1.2665 (5)	0.0678 (14)
H26A	0.6878	0.3147	1.3329	0.081*
C27	0.67852 (19)	0.30681 (18)	1.1667 (5)	0.0573 (12)
C28	0.7031 (2)	0.2953 (2)	1.0702 (5)	0.0757 (16)
H28A	0.6842	0.2953	1.0030	0.091*
C29	0.7582 (2)	0.2831 (2)	1.0716 (5)	0.0792 (18)
H29A	0.7756	0.2755	1.0047	0.095*
Cl4	0.953 (3)	0.4309 (11)	0.3672 (15)	0.106 (3)	0.50
C32	0.9339 (8)	0.3445 (7)	0.6961 (12)	0.094 (10)	0.50
C33	0.9278 (9)	0.3172 (5)	0.5954 (16)	0.074 (8)	0.50
H33A	0.9182	0.2814	0.5955	0.088*	0.50
C34	0.9360 (8)	0.3437 (7)	0.4944 (12)	0.082 (9)	0.50
H34A	0.9320	0.3255	0.4269	0.099*	0.50
C35	0.9504 (9)	0.3973 (7)	0.4941 (10)	0.137 (14)	0.50
C36	0.9565 (7)	0.4245 (5)	0.5949 (13)	0.113 (9)	0.50
H36A	0.9660	0.4604	0.5947	0.136*	0.50
C37	0.9482 (5)	0.3981 (7)	0.6959 (10)	0.098 (6)	0.50
H37A	0.9523	0.4163	0.7633	0.118*	0.50
Cl4'	0.958 (3)	0.4283 (11)	0.3637 (16)	0.106 (3)	0.50
C32'	0.9229 (7)	0.3403 (6)	0.6855 (9)	0.056 (4)	0.50
C33'	0.9332 (9)	0.3122 (4)	0.5873 (13)	0.080 (10)	0.50
H33B	0.9333	0.2751	0.5878	0.096*	0.50
C34'	0.9433 (8)	0.3397 (4)	0.4883 (9)	0.080 (9)	0.50
H34B	0.9502	0.3209	0.4226	0.096*	0.50
C35'	0.9431 (6)	0.3952 (4)	0.4875 (8)	0.051 (4)	0.50
C36'	0.9328 (6)	0.4232 (4)	0.5857 (10)	0.082 (5)	0.50
H36B	0.9327	0.4604	0.5852	0.099*	0.50
C37'	0.9227 (5)	0.3958 (6)	0.6847 (8)	0.077 (5)	0.50
H37B	0.9158	0.4145	0.7504	0.093*	0.50
C31	0.9144 (3)	0.3121 (2)	0.7952 (4)	0.086 (2)
H31A	0.8974	0.2784	0.7814	0.103*	0.50
H31B	0.9237	0.2749	0.7915	0.103*	0.30
H31C	0.9237	0.2749	0.7915	0.103*	0.20
C30	0.9177 (3)	0.3236 (4)	0.9009 (8)	0.064 (4)	0.50
C38	0.9523 (4)	0.3689 (4)	0.9341 (10)	0.079 (3)	0.50
H38A	0.9760	0.3568	0.9932	0.095*	0.50
H38B	0.9743	0.3786	0.8704	0.095*	0.50
C39	0.9241 (6)	0.4170 (4)	0.9735 (11)	0.107 (7)	0.50
H39A	0.9178	0.4399	0.9092	0.128*	0.50
H39B	0.9478	0.4361	1.0237	0.128*	0.50
C40	0.8728 (5)	0.4090 (5)	1.0317 (11)	0.086 (4)	0.50
H40A	0.8460	0.3994	0.9765	0.103*	0.50
H40B	0.8620	0.4427	1.0647	0.103*	0.50
C30'	0.8957 (6)	0.3301 (7)	0.8904 (11)	0.034 (4)	0.30
C38'	0.8600 (9)	0.3781 (9)	0.8937 (18)	0.092 (6)	0.30
H38C	0.8269	0.3692	0.9313	0.110*	0.30
H38D	0.8516	0.3893	0.8179	0.110*	0.30
C39'	0.8875 (12)	0.4233 (6)	0.9555 (11)	0.119 (14)	0.30
H39C	0.8619	0.4515	0.9708	0.143*	0.30
H39D	0.9157	0.4381	0.9090	0.143*	0.30
C40'	0.9111 (7)	0.4033 (7)	1.0653 (14)	0.087 (7)	0.30
H40C	0.9442	0.3844	1.0504	0.104*	0.30
H40D	0.9192	0.4334	1.1136	0.104*	0.30
C30"	0.8910 (7)	0.3266 (15)	0.8900 (19)	0.064 (4)	0.20
C38"	0.8706 (16)	0.3843 (19)	0.882 (3)	0.092 (6)	0.20
H38E	0.8972	0.4089	0.9104	0.110*	0.20
H38F	0.8633	0.3934	0.8041	0.110*	0.20
C39"	0.8201 (10)	0.3880 (12)	0.9503 (15)	0.106 (11)	0.20
H39E	0.7964	0.4141	0.9165	0.127*	0.20
H39F	0.8022	0.3537	0.9496	0.127*	0.20
C40"	0.8312 (11)	0.4039 (10)	1.0693 (16)	0.079 (9)	0.20
H40E	0.7983	0.4025	1.1122	0.095*	0.20
H40F	0.8442	0.4404	1.0711	0.095*	0.20
C41	0.8728 (3)	0.3667 (2)	1.1232 (5)	0.0809 (17)
H41A	0.9041	0.3716	1.1686	0.097*	0.50
H41B	0.8423	0.3725	1.1704	0.097*	0.50
H41C	0.8812	0.3672	1.2017	0.097*	0.30
H41D	0.8378	0.3817	1.1143	0.097*	0.30
H41E	0.9068	0.3823	1.1050	0.097*	0.20
H41F	0.8688	0.3676	1.2032	0.097*	0.20

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0590 (7)	0.0495 (6)	0.0410 (6)	0.0031 (5)	0.0016 (5)	−0.0026 (5)
Cl1	0.0925 (12)	0.1111 (14)	0.193 (2)	0.0435 (11)	−0.0403 (14)	−0.0532 (16)
Cl2	0.1005 (13)	0.1114 (13)	0.1343 (17)	−0.0073 (10)	−0.0487 (13)	−0.0048 (12)
Cl3	0.0586 (8)	0.0682 (8)	0.1093 (12)	0.0072 (6)	−0.0049 (8)	−0.0023 (8)
N1	0.055 (2)	0.046 (2)	0.041 (2)	−0.0061 (17)	0.0010 (17)	0.0006 (17)
N2	0.051 (2)	0.054 (2)	0.042 (2)	0.0080 (18)	0.0027 (17)	−0.0059 (18)
N3	0.067 (3)	0.072 (3)	0.052 (2)	0.002 (2)	0.008 (2)	0.017 (2)
N4	0.052 (2)	0.080 (3)	0.063 (3)	0.016 (2)	0.010 (2)	−0.015 (2)
O1	0.078 (2)	0.061 (2)	0.064 (2)	0.0044 (18)	−0.0014 (19)	−0.0130 (19)
O2	0.074 (2)	0.080 (2)	0.0426 (19)	0.0193 (18)	0.0127 (17)	0.0001 (17)
C1	0.050 (2)	0.053 (3)	0.045 (3)	0.008 (2)	0.007 (2)	0.003 (2)
C2	0.053 (3)	0.059 (3)	0.068 (3)	0.006 (2)	0.010 (3)	0.007 (3)
C3	0.077 (4)	0.071 (4)	0.072 (4)	−0.009 (3)	0.006 (3)	0.019 (3)
C4	0.055 (3)	0.058 (3)	0.042 (3)	0.006 (2)	0.007 (2)	0.004 (2)
C5	0.061 (3)	0.063 (3)	0.049 (3)	0.019 (3)	0.002 (2)	0.004 (3)
C6	0.054 (3)	0.068 (3)	0.052 (3)	0.008 (2)	−0.004 (2)	−0.006 (2)
C7	0.060 (3)	0.061 (3)	0.042 (3)	0.013 (2)	−0.004 (2)	0.001 (2)
C8	0.061 (3)	0.079 (4)	0.062 (3)	0.015 (3)	−0.006 (3)	−0.007 (3)
C9	0.085 (4)	0.097 (4)	0.064 (4)	0.013 (4)	−0.020 (3)	−0.016 (3)
C10	0.066 (4)	0.113 (5)	0.084 (4)	−0.001 (4)	−0.015 (3)	−0.018 (4)
C11	0.053 (3)	0.119 (5)	0.081 (4)	0.007 (3)	−0.003 (3)	−0.018 (4)
C12	0.096 (4)	0.098 (4)	0.069 (4)	0.014 (4)	0.002 (3)	0.032 (3)
C13	0.045 (3)	0.051 (3)	0.074 (3)	−0.005 (2)	−0.001 (2)	0.008 (3)
C14	0.053 (3)	0.066 (3)	0.125 (6)	0.008 (3)	0.005 (3)	−0.005 (4)
C15	0.056 (3)	0.085 (4)	0.119 (6)	0.005 (3)	−0.021 (4)	0.000 (4)
C16	0.069 (4)	0.066 (4)	0.102 (5)	−0.009 (3)	−0.017 (3)	0.010 (4)
C17	0.076 (4)	0.060 (3)	0.094 (5)	0.002 (3)	−0.013 (3)	−0.004 (3)
C18	0.063 (3)	0.057 (3)	0.093 (4)	0.004 (2)	−0.005 (3)	−0.001 (3)
C19	0.046 (3)	0.063 (3)	0.043 (3)	0.007 (2)	−0.002 (2)	0.003 (2)
C20	0.041 (2)	0.051 (3)	0.045 (3)	0.0018 (19)	−0.006 (2)	−0.013 (2)
C21	0.071 (3)	0.050 (3)	0.052 (3)	−0.005 (2)	−0.002 (3)	−0.004 (2)
C22	0.069 (3)	0.051 (3)	0.062 (3)	0.003 (2)	0.001 (3)	−0.005 (3)
C23	0.055 (3)	0.056 (3)	0.043 (3)	0.003 (2)	−0.005 (2)	−0.014 (2)
C24	0.053 (3)	0.052 (3)	0.051 (3)	0.008 (2)	−0.005 (2)	−0.005 (2)
C25	0.066 (3)	0.072 (3)	0.045 (3)	0.011 (3)	0.000 (2)	0.008 (2)
C26	0.070 (4)	0.077 (4)	0.056 (3)	0.010 (3)	0.017 (3)	0.008 (3)
C27	0.057 (3)	0.049 (3)	0.066 (3)	0.004 (2)	−0.005 (3)	0.003 (2)
C28	0.068 (4)	0.098 (4)	0.061 (4)	0.018 (3)	−0.016 (3)	−0.017 (3)
C29	0.078 (4)	0.108 (5)	0.052 (3)	0.030 (3)	−0.016 (3)	−0.024 (3)
Cl4	0.140 (8)	0.099 (2)	0.0795 (13)	−0.005 (3)	−0.0026 (18)	0.0287 (14)
C32	0.123 (18)	0.062 (13)	0.097 (16)	−0.034 (11)	0.011 (12)	0.015 (12)
C33	0.059 (11)	0.060 (12)	0.10 (2)	0.001 (9)	0.027 (12)	−0.010 (13)
C34	0.053 (9)	0.13 (2)	0.060 (14)	−0.007 (10)	0.022 (9)	−0.024 (13)
C35	0.149 (16)	0.128 (16)	0.134 (16)	−0.002 (9)	0.004 (9)	0.002 (10)
C36	0.18 (3)	0.070 (11)	0.085 (13)	−0.022 (10)	0.023 (13)	0.010 (10)
C37	0.104 (13)	0.087 (11)	0.104 (12)	−0.034 (10)	−0.003 (10)	0.012 (9)
Cl4'	0.140 (8)	0.099 (2)	0.0795 (13)	−0.005 (3)	−0.0026 (18)	0.0287 (14)
C32'	0.077 (9)	0.041 (9)	0.049 (9)	−0.013 (7)	0.019 (7)	−0.008 (7)
C33'	0.15 (3)	0.047 (10)	0.048 (12)	−0.018 (11)	0.039 (13)	−0.006 (9)
C34'	0.121 (19)	0.047 (10)	0.073 (15)	0.000 (10)	0.038 (12)	0.012 (9)
C35'	0.059 (7)	0.037 (7)	0.057 (7)	−0.012 (5)	0.005 (5)	0.005 (5)
C36'	0.109 (14)	0.040 (7)	0.099 (13)	−0.011 (7)	−0.004 (9)	0.007 (8)
C37'	0.107 (9)	0.062 (7)	0.063 (7)	−0.016 (7)	0.008 (6)	−0.002 (6)
C31	0.137 (6)	0.045 (3)	0.076 (4)	−0.004 (3)	0.031 (4)	−0.002 (3)
C30	0.062 (7)	0.057 (6)	0.073 (7)	0.004 (6)	0.003 (6)	−0.005 (5)
C38	0.088 (8)	0.083 (8)	0.068 (7)	−0.016 (7)	0.010 (6)	−0.001 (6)
C39	0.20 (2)	0.066 (10)	0.055 (8)	−0.034 (11)	−0.005 (11)	0.016 (7)
C40	0.092 (8)	0.073 (7)	0.094 (8)	−0.006 (7)	0.019 (7)	−0.018 (7)
C30'	0.040 (8)	0.028 (9)	0.033 (9)	−0.001 (7)	−0.016 (7)	0.003 (7)
C38'	0.108 (15)	0.077 (11)	0.091 (11)	0.020 (10)	0.038 (10)	0.002 (9)
C39'	0.23 (4)	0.048 (14)	0.080 (19)	0.042 (19)	−0.02 (2)	−0.030 (13)
C40'	0.117 (19)	0.040 (10)	0.103 (18)	−0.034 (12)	0.018 (15)	−0.009 (11)
C30"	0.062 (7)	0.057 (6)	0.073 (7)	0.004 (6)	0.003 (6)	−0.005 (5)
C38"	0.108 (15)	0.077 (11)	0.091 (11)	0.020 (10)	0.038 (10)	0.002 (9)
C39"	0.106 (14)	0.100 (14)	0.111 (14)	0.001 (9)	−0.004 (10)	−0.002 (9)
C40"	0.11 (2)	0.056 (16)	0.070 (19)	0.044 (17)	0.004 (17)	−0.006 (14)
C41	0.104 (4)	0.061 (3)	0.078 (4)	0.006 (3)	0.003 (3)	−0.024 (3)

Geometric parameters (Å, º) top

S1—C20	1.753 (4)	Cl4—C35	1.733 (8)
S1—C1	1.832 (5)	C32—C33	1.3900
Cl1—C14	1.739 (6)	C32—C37	1.3900
Cl2—C16	1.724 (7)	C32—C31	1.513 (8)
Cl3—C27	1.741 (5)	C33—C34	1.3900
N1—C20	1.264 (6)	C33—H33A	0.9300
N1—C21	1.439 (6)	C34—C35	1.3900
N2—C19	1.370 (6)	C34—H34A	0.9300
N2—C20	1.394 (6)	C35—C36	1.3900
N2—C23	1.481 (6)	C36—C37	1.3900
N3—C12	1.455 (7)	C36—H36A	0.9300
N3—C3	1.456 (7)	C37—H37A	0.9300
N3—C4	1.457 (6)	Cl4'—C35'	1.732 (8)
N4—C5	1.363 (6)	C32'—C33'	1.3900
N4—C6	1.406 (6)	C32'—C37'	1.3900
N4—H4	0.8600	C32'—C31	1.502 (7)
O1—C5	1.217 (6)	C33'—C34'	1.3900
O2—C19	1.204 (5)	C33'—H33B	0.9300
C1—C19	1.529 (7)	C34'—C35'	1.3900
C1—C4	1.581 (6)	C34'—H34B	0.9300
C1—C2	1.584 (7)	C35'—C36'	1.3900
C2—C13	1.492 (7)	C36'—C37'	1.3900
C2—C3	1.521 (7)	C36'—H36B	0.9300
C2—H2A	0.9800	C37'—H37B	0.9300
C3—H3A	0.9700	C31—C30	1.296 (9)
C3—H3B	0.9700	C31—C30'	1.309 (9)
C4—C7	1.512 (7)	C31—C30"	1.324 (10)
C4—C5	1.563 (7)	C31—H31A	0.9600
C6—C11	1.366 (8)	C31—H31B	0.9600
C6—C7	1.389 (7)	C31—H31C	0.9600
C7—C8	1.376 (7)	C30—C38	1.480 (9)
C8—C9	1.407 (8)	C38—C39	1.472 (8)
C8—H8A	0.9300	C38—H38A	0.9700
C9—C10	1.362 (8)	C38—H38B	0.9700
C9—H9A	0.9300	C39—C40	1.475 (9)
C10—C11	1.380 (9)	C39—H39A	0.9700
C10—H10A	0.9300	C39—H39B	0.9700
C11—H11A	0.9300	C40—C41	1.521 (9)
C12—H12A	0.9600	C40—H40A	0.9700
C12—H12B	0.9600	C40—H40B	0.9700
C12—H12C	0.9600	C30'—C38'	1.498 (10)
C13—C14	1.381 (7)	C38'—C39'	1.516 (10)
C13—C18	1.395 (7)	C38'—H38C	0.9700
C14—C15	1.386 (9)	C38'—H38D	0.9700
C15—C16	1.350 (9)	C39'—C40'	1.522 (9)
C15—H15A	0.9300	C39'—H39C	0.9700
C16—C17	1.365 (8)	C39'—H39D	0.9700
C17—C18	1.388 (8)	C40'—C41	1.495 (9)
C17—H17A	0.9300	C40'—H40C	0.9700
C18—H18A	0.9300	C40'—H40D	0.9700
C21—C22	1.351 (7)	C40'—H41E	0.7161
C21—C30"	1.44 (4)	C30"—C38"	1.54 (5)
C21—C30	1.499 (13)	C38"—C39"	1.508 (10)
C21—C30'	1.50 (2)	C38"—H38E	0.9700
C22—C23	1.505 (7)	C38"—H38F	0.9700
C22—C41	1.505 (7)	C39"—C40"	1.500 (10)
C23—C24	1.510 (6)	C39"—H39E	0.9700
C23—H23A	0.9800	C39"—H39F	0.9700
C24—C29	1.372 (7)	C40"—C41	1.540 (10)
C24—C25	1.378 (7)	C40"—H40E	0.9700
C25—C26	1.383 (7)	C40"—H40F	0.9700
C25—H25A	0.9300	C40"—H41D	0.7908
C26—C27	1.369 (7)	C41—H41A	0.9602
C26—H26A	0.9300	C41—H41B	0.9600
C27—C28	1.337 (7)	C41—H41C	0.9601
C28—C29	1.413 (8)	C41—H41D	0.9599
C28—H28A	0.9300	C41—H41E	0.9602
C29—H29A	0.9300	C41—H41F	0.9600

C20—S1—C1	94.0 (2)	C30'—C31—C30"	6.3 (13)
C20—N1—C21	116.9 (4)	C30—C31—C32'	137.2 (9)
C19—N2—C20	117.4 (4)	C30'—C31—C32'	130.2 (12)
C19—N2—C23	122.5 (4)	C30"—C31—C32'	133 (2)
C20—N2—C23	119.2 (4)	C30—C31—C32	128.3 (11)
C12—N3—C3	114.9 (5)	C30'—C31—C32	127.5 (13)
C12—N3—C4	115.1 (4)	C30"—C31—C32	132 (2)
C3—N3—C4	106.9 (4)	C32'—C31—C32	12.2 (14)
C5—N4—C6	112.0 (4)	C30—C31—H31A	113.0
C5—N4—H4	124.0	C30'—C31—H31A	107.0
C6—N4—H4	124.0	C30"—C31—H31A	101.1
C19—C1—C4	111.0 (4)	C32'—C31—H31A	109.0
C19—C1—C2	109.9 (4)	C32—C31—H31A	118.7
C4—C1—C2	103.6 (3)	C30—C31—H31B	104.2
C19—C1—S1	104.7 (3)	C30'—C31—H31B	117.4
C4—C1—S1	111.6 (3)	C30"—C31—H31B	114.3
C2—C1—S1	116.3 (3)	C32'—C31—H31B	112.4
C13—C2—C3	117.9 (4)	C32—C31—H31B	113.9
C13—C2—C1	115.8 (4)	H31A—C31—H31B	41.2
C3—C2—C1	104.6 (4)	C30—C31—H31C	104.2
C13—C2—H2A	105.8	C30'—C31—H31C	117.4
C3—C2—H2A	105.8	C30"—C31—H31C	114.3
C1—C2—H2A	105.8	C32'—C31—H31C	112.4
N3—C3—C2	104.2 (4)	C32—C31—H31C	113.9
N3—C3—H3A	110.9	H31A—C31—H31C	41.2
C2—C3—H3A	110.9	H31B—C31—H31C	0.0
N3—C3—H3B	110.9	C31—C30—C38	117.9 (11)
C2—C3—H3B	110.9	C31—C30—C21	119.4 (8)
H3A—C3—H3B	108.9	C38—C30—C21	122.7 (8)
N3—C4—C7	114.2 (4)	C39—C38—C30	115.6 (7)
N3—C4—C5	112.9 (4)	C39—C38—H38A	108.4
C7—C4—C5	101.7 (4)	C30—C38—H38A	108.4
N3—C4—C1	102.3 (3)	C39—C38—H38B	108.4
C7—C4—C1	117.2 (4)	C30—C38—H38B	108.4
C5—C4—C1	108.8 (4)	H38A—C38—H38B	107.4
O1—C5—N4	125.4 (4)	C38—C39—C40	117.2 (7)
O1—C5—C4	127.2 (5)	C38—C39—H39A	108.0
N4—C5—C4	107.4 (4)	C40—C39—H39A	108.0
C11—C6—C7	122.8 (5)	C38—C39—H39B	108.0
C11—C6—N4	127.5 (5)	C40—C39—H39B	108.0
C7—C6—N4	109.7 (4)	H39A—C39—H39B	107.2
C8—C7—C6	118.9 (5)	C39—C40—C41	115.5 (8)
C8—C7—C4	131.7 (4)	C39—C40—H40A	108.4
C6—C7—C4	109.1 (4)	C41—C40—H40A	108.4
C7—C8—C9	118.5 (5)	C39—C40—H40B	108.4
C7—C8—H8A	120.8	C41—C40—H40B	108.4
C9—C8—H8A	120.8	H40A—C40—H40B	107.5
C10—C9—C8	120.8 (6)	C39—C40—H41D	152.7
C10—C9—H9A	119.6	C41—C40—H41D	37.2
C8—C9—H9A	119.6	H40A—C40—H41D	86.0
C9—C10—C11	121.1 (6)	H40B—C40—H41D	88.2
C9—C10—H10A	119.4	C39—C40—H41E	80.0
C11—C10—H10A	119.4	C41—C40—H41E	38.2
C6—C11—C10	117.8 (5)	H40A—C40—H41E	136.9
C6—C11—H11A	121.1	H40B—C40—H41E	109.5
C10—C11—H11A	121.1	H41D—C40—H41E	73.9
N3—C12—H12A	109.5	C31—C30'—C38'	120.9 (16)
N3—C12—H12B	109.5	C31—C30'—C21	118.3 (13)
H12A—C12—H12B	109.5	C38'—C30'—C21	114.6 (12)
N3—C12—H12C	109.5	C30'—C38'—C39'	110.0 (9)
H12A—C12—H12C	109.5	C30'—C38'—H38C	109.7
H12B—C12—H12C	109.5	C39'—C38'—H38C	109.7
C14—C13—C18	115.1 (5)	C30'—C38'—H38D	109.7
C14—C13—C2	123.0 (5)	C39'—C38'—H38D	109.7
C18—C13—C2	121.9 (4)	H38C—C38'—H38D	108.2
C13—C14—C15	123.4 (6)	C38'—C39'—C40'	110.4 (8)
C13—C14—Cl1	119.6 (5)	C38'—C39'—H39C	109.6
C15—C14—Cl1	117.0 (5)	C40'—C39'—H39C	109.6
C16—C15—C14	119.2 (5)	C38'—C39'—H39D	109.6
C16—C15—H15A	120.4	C40'—C39'—H39D	109.6
C14—C15—H15A	120.4	H39C—C39'—H39D	108.1
C15—C16—C17	120.4 (6)	C41—C40'—C39'	110.5 (9)
C15—C16—Cl2	120.4 (5)	C41—C40'—H40C	109.6
C17—C16—Cl2	119.2 (5)	C39'—C40'—H40C	109.6
C16—C17—C18	119.7 (6)	C41—C40'—H40D	109.6
C16—C17—H17A	120.1	C39'—C40'—H40D	109.6
C18—C17—H17A	120.1	H40C—C40'—H40D	108.1
C17—C18—C13	122.1 (5)	C41—C40'—H41A	37.7
C17—C18—H18A	119.0	C39'—C40'—H41A	148.1
C13—C18—H18A	119.0	H40C—C40'—H41A	89.6
O2—C19—N2	122.6 (4)	H40D—C40'—H41A	86.9
O2—C19—C1	124.3 (4)	C41—C40'—H41E	31.5
N2—C19—C1	113.2 (4)	C39'—C40'—H41E	138.8
N1—C20—N2	126.8 (4)	H40C—C40'—H41E	83.9
N1—C20—S1	122.9 (3)	H40D—C40'—H41E	102.1
N2—C20—S1	110.3 (3)	H41A—C40'—H41E	15.2
C22—C21—C30"	121.1 (9)	C31—C30"—C21	122 (3)
C22—C21—N1	122.1 (4)	C31—C30"—C38"	110 (3)
C30"—C21—N1	115.2 (9)	C21—C30"—C38"	127.5 (11)
C22—C21—C30	123.7 (5)	C39"—C38"—C30"	108 (3)
C30"—C21—C30	26.8 (8)	C39"—C38"—H38E	110.2
N1—C21—C30	112.5 (4)	C30"—C38"—H38E	110.2
C22—C21—C30'	119.5 (6)	C39"—C38"—H38F	110.2
C30"—C21—C30'	5.1 (9)	C30"—C38"—H38F	110.2
N1—C21—C30'	117.7 (6)	H38E—C38"—H38F	108.5
C30—C21—C30'	22.6 (6)	C40"—C39"—C38"	112.1 (10)
C21—C22—C23	120.8 (4)	C40"—C39"—H39E	109.2
C21—C22—C41	125.6 (5)	C38"—C39"—H39E	109.2
C23—C22—C41	113.1 (4)	C40"—C39"—H39F	109.2
N2—C23—C22	110.0 (4)	C38"—C39"—H39F	109.2
N2—C23—C24	111.9 (4)	H39E—C39"—H39F	107.9
C22—C23—C24	109.5 (4)	C39"—C40"—C41	111.0 (9)
N2—C23—H23A	108.5	C39"—C40"—H40E	109.4
C22—C23—H23A	108.5	C41—C40"—H40E	109.4
C24—C23—H23A	108.5	C39"—C40"—H40F	109.4
C29—C24—C25	118.1 (4)	C41—C40"—H40F	109.4
C29—C24—C23	120.4 (5)	H40E—C40"—H40F	108.0
C25—C24—C23	121.5 (4)	C39"—C40"—H41B	132.2
C24—C25—C26	120.9 (5)	C41—C40"—H41B	37.2
C24—C25—H25A	119.5	H40E—C40"—H41B	73.0
C26—C25—H25A	119.5	H40F—C40"—H41B	115.0
C27—C26—C25	119.6 (5)	C39"—C40"—H41D	119.6
C27—C26—H26A	120.2	C41—C40"—H41D	31.6
C25—C26—H26A	120.2	H40E—C40"—H41D	78.2
C28—C27—C26	121.4 (5)	H40F—C40"—H41D	125.3
C28—C27—Cl3	118.6 (4)	H41B—C40"—H41D	12.8
C26—C27—Cl3	120.0 (4)	C40'—C41—C22	117.3 (9)
C27—C28—C29	119.0 (5)	C40'—C41—C40	40.8 (8)
C27—C28—H28A	120.5	C22—C41—C40	117.1 (7)
C29—C28—H28A	120.5	C40'—C41—C40"	82.6 (15)
C24—C29—C28	121.0 (5)	C22—C41—C40"	116.7 (10)
C24—C29—H29A	119.5	C40—C41—C40"	43.8 (13)
C28—C29—H29A	119.5	C40'—C41—H41A	70.0
C33—C32—C37	120.0	C22—C41—H41A	107.3
C33—C32—C31	112.2 (13)	C40—C41—H41A	108.4
C37—C32—C31	127.0 (13)	C40"—C41—H41A	135.3
C34—C33—C32	120.0	C40'—C41—H41B	133.4
C34—C33—H33A	120.0	C22—C41—H41B	108.0
C32—C33—H33A	120.0	C40—C41—H41B	108.3
C35—C34—C33	120.0	C40"—C41—H41B	67.2
C35—C34—H34A	120.0	H41A—C41—H41B	107.4
C33—C34—H34A	120.0	C40'—C41—H41C	107.7
C34—C35—C36	120.0	C22—C41—H41C	107.5
C34—C35—Cl4	118.7 (7)	C40—C41—H41C	133.8
C36—C35—Cl4	120.9 (7)	C40"—C41—H41C	123.2
C37—C36—C35	120.0	H41A—C41—H41C	43.1
C37—C36—H36A	120.0	H41B—C41—H41C	66.4
C35—C36—H36A	120.0	C40'—C41—H41D	107.2
C36—C37—C32	120.0	C22—C41—H41D	109.3
C36—C37—H37A	120.0	C40—C41—H41D	69.3
C32—C37—H37A	120.0	C40"—C41—H41D	25.6
C33'—C32'—C37'	120.0	H41A—C41—H41D	139.3
C33'—C32'—C31	121.6 (10)	H41B—C41—H41D	43.8
C37'—C32'—C31	118.4 (10)	H41C—C41—H41D	107.6
C34'—C33'—C32'	120.0	C40'—C41—H41E	22.9
C34'—C33'—H33B	120.0	C22—C41—H41E	109.4
C32'—C33'—H33B	120.0	C40—C41—H41E	63.6
C33'—C34'—C35'	120.0	C40"—C41—H41E	105.1
C33'—C34'—H34B	120.0	H41A—C41—H41E	49.7
C35'—C34'—H34B	120.0	H41B—C41—H41E	140.8
C36'—C35'—C34'	120.0	H41C—C41—H41E	91.3
C36'—C35'—Cl4'	121.0 (7)	H41D—C41—H41E	128.7
C34'—C35'—Cl4'	118.9 (7)	C40'—C41—H41F	120.8
C35'—C36'—C37'	120.0	C22—C41—H41F	108.3
C35'—C36'—H36B	120.0	C40—C41—H41F	134.1
C37'—C36'—H36B	120.0	C40"—C41—H41F	109.1
C36'—C37'—C32'	120.0	H41A—C41—H41F	61.5
C36'—C37'—H37B	120.0	H41B—C41—H41F	47.8
C32'—C37'—H37B	120.0	H41C—C41—H41F	18.7
C30—C31—C30'	26.1 (8)	H41D—C41—H41F	90.2
C30—C31—C30"	30.2 (10)	H41E—C41—H41F	108.0

C20—S1—C1—C19	5.4 (3)	C24—C25—C26—C27	1.3 (8)
C20—S1—C1—C4	−114.7 (3)	C25—C26—C27—C28	−0.3 (8)
C20—S1—C1—C2	126.8 (3)	C25—C26—C27—Cl3	−179.3 (4)
C19—C1—C2—C13	109.9 (5)	C26—C27—C28—C29	−0.7 (9)
C4—C1—C2—C13	−131.5 (4)	Cl3—C27—C28—C29	178.3 (5)
S1—C1—C2—C13	−8.8 (5)	C25—C24—C29—C28	0.4 (8)
C19—C1—C2—C3	−118.6 (4)	C23—C24—C29—C28	−176.4 (5)
C4—C1—C2—C3	0.0 (5)	C27—C28—C29—C24	0.6 (9)
S1—C1—C2—C3	122.8 (4)	C37—C32—C33—C34	0.0
C12—N3—C3—C2	−172.0 (4)	C31—C32—C33—C34	170.4 (17)
C4—N3—C3—C2	−42.8 (5)	C32—C33—C34—C35	0.0
C13—C2—C3—N3	154.9 (4)	C33—C34—C35—C36	0.0
C1—C2—C3—N3	24.5 (5)	C33—C34—C35—Cl4	−173 (3)
C12—N3—C4—C7	−61.3 (6)	C34—C35—C36—C37	0.0
C3—N3—C4—C7	169.6 (4)	Cl4—C35—C36—C37	173 (3)
C12—N3—C4—C5	54.2 (6)	C35—C36—C37—C32	0.0
C3—N3—C4—C5	−74.8 (5)	C33—C32—C37—C36	0.0
C12—N3—C4—C1	170.9 (5)	C31—C32—C37—C36	−168.8 (19)
C3—N3—C4—C1	41.9 (5)	C37'—C32'—C33'—C34'	0.0
C19—C1—C4—N3	93.5 (4)	C31—C32'—C33'—C34'	−177.0 (15)
C2—C1—C4—N3	−24.3 (5)	C32'—C33'—C34'—C35'	0.0
S1—C1—C4—N3	−150.2 (3)	C33'—C34'—C35'—C36'	0.0
C19—C1—C4—C7	−32.3 (5)	C33'—C34'—C35'—Cl4'	178 (3)
C2—C1—C4—C7	−150.1 (4)	C34'—C35'—C36'—C37'	0.0
S1—C1—C4—C7	84.0 (4)	Cl4'—C35'—C36'—C37'	−178 (3)
C19—C1—C4—C5	−146.9 (4)	C35'—C36'—C37'—C32'	0.0
C2—C1—C4—C5	95.3 (4)	C33'—C32'—C37'—C36'	0.0
S1—C1—C4—C5	−30.6 (4)	C31—C32'—C37'—C36'	177.1 (14)
C6—N4—C5—O1	−178.3 (5)	C33'—C32'—C31—C30	158.0 (10)
C6—N4—C5—C4	−0.4 (5)	C37'—C32'—C31—C30	−19 (2)
N3—C4—C5—O1	55.8 (7)	C33'—C32'—C31—C30'	−166.9 (12)
C7—C4—C5—O1	178.7 (5)	C37'—C32'—C31—C30'	16 (2)
C1—C4—C5—O1	−57.0 (6)	C33'—C32'—C31—C30"	−159.2 (11)
N3—C4—C5—N4	−122.0 (4)	C37'—C32'—C31—C30"	24 (2)
C7—C4—C5—N4	0.9 (5)	C33'—C32'—C31—C32	111 (7)
C1—C4—C5—N4	125.2 (4)	C37'—C32'—C31—C32	−66 (6)
C5—N4—C6—C11	178.8 (6)	C33—C32—C31—C30	174.6 (8)
C5—N4—C6—C7	−0.2 (6)	C37—C32—C31—C30	−16 (2)
C11—C6—C7—C8	−3.3 (8)	C33—C32—C31—C30'	−152.2 (13)
N4—C6—C7—C8	175.8 (5)	C37—C32—C31—C30'	17 (2)
C11—C6—C7—C4	−178.3 (5)	C33—C32—C31—C30"	−145.9 (15)
N4—C6—C7—C4	0.8 (6)	C37—C32—C31—C30"	24 (2)
N3—C4—C7—C8	−53.2 (7)	C33—C32—C31—C32'	−45 (6)
C5—C4—C7—C8	−175.1 (5)	C37—C32—C31—C32'	125 (7)
C1—C4—C7—C8	66.4 (7)	C30'—C31—C30—C38	−110 (2)
N3—C4—C7—C6	120.9 (4)	C30"—C31—C30—C38	−120 (4)
C5—C4—C7—C6	−1.0 (5)	C32'—C31—C30—C38	−23.0 (13)
C1—C4—C7—C6	−119.5 (4)	C32—C31—C30—C38	−11.6 (12)
C6—C7—C8—C9	3.4 (8)	C30'—C31—C30—C21	70 (2)
C4—C7—C8—C9	177.1 (5)	C30"—C31—C30—C21	60 (4)
C7—C8—C9—C10	−2.1 (9)	C32'—C31—C30—C21	157.3 (12)
C8—C9—C10—C11	0.4 (10)	C32—C31—C30—C21	168.7 (12)
C7—C6—C11—C10	1.6 (10)	C22—C21—C30—C31	−156.0 (6)
N4—C6—C11—C10	−177.3 (6)	C30"—C21—C30—C31	−62.8 (19)
C9—C10—C11—C6	−0.1 (10)	N1—C21—C30—C31	38.8 (5)
C3—C2—C13—C14	145.8 (5)	C30'—C21—C30—C31	−69.6 (15)
C1—C2—C13—C14	−89.2 (6)	C22—C21—C30—C38	24.3 (6)
C3—C2—C13—C18	−35.2 (7)	C30"—C21—C30—C38	117.5 (19)
C1—C2—C13—C18	89.8 (6)	N1—C21—C30—C38	−140.9 (5)
C18—C13—C14—C15	4.1 (9)	C30'—C21—C30—C38	110.7 (15)
C2—C13—C14—C15	−176.8 (6)	C31—C30—C38—C39	109.1 (10)
C18—C13—C14—Cl1	−175.8 (4)	C21—C30—C38—C39	−71.2 (10)
C2—C13—C14—Cl1	3.3 (8)	C30—C38—C39—C40	31.4 (17)
C13—C14—C15—C16	−3.8 (10)	C38—C39—C40—C41	47.9 (18)
Cl1—C14—C15—C16	176.1 (5)	C30—C31—C30'—C38'	141 (3)
C14—C15—C16—C17	0.9 (10)	C32'—C31—C30'—C38'	24 (2)
C14—C15—C16—Cl2	179.8 (5)	C32—C31—C30'—C38'	39 (2)
C15—C16—C17—C18	1.3 (9)	C30—C31—C30'—C21	−68 (2)
Cl2—C16—C17—C18	−177.6 (5)	C32'—C31—C30'—C21	174.4 (12)
C16—C17—C18—C13	−0.8 (9)	C32—C31—C30'—C21	−170.3 (12)
C14—C13—C18—C17	−1.8 (8)	C22—C21—C30'—C31	174.1 (9)
C2—C13—C18—C17	179.1 (5)	C30"—C21—C30'—C31	−76 (14)
C20—N2—C19—O2	−173.7 (4)	N1—C21—C30'—C31	−15.4 (15)
C23—N2—C19—O2	−4.7 (7)	C30—C21—C30'—C31	66.7 (16)
C20—N2—C19—C1	5.8 (5)	C22—C21—C30'—C38'	−33.3 (13)
C23—N2—C19—C1	174.9 (4)	C30"—C21—C30'—C38'	76 (15)
C4—C1—C19—O2	−67.1 (6)	N1—C21—C30'—C38'	137.1 (9)
C2—C1—C19—O2	46.8 (6)	C30—C21—C30'—C38'	−141 (2)
S1—C1—C19—O2	172.4 (4)	C31—C30'—C38'—C39'	−115.0 (17)
C4—C1—C19—N2	113.4 (4)	C21—C30'—C38'—C39'	93.2 (16)
C2—C1—C19—N2	−132.7 (4)	C30'—C38'—C39'—C40'	−48 (2)
S1—C1—C19—N2	−7.1 (4)	C38'—C39'—C40'—C41	−43 (2)
C21—N1—C20—N2	3.9 (6)	C30—C31—C30"—C21	−68 (4)
C21—N1—C20—S1	−174.7 (3)	C32'—C31—C30"—C21	178.4 (12)
C19—N2—C20—N1	179.9 (4)	C32—C31—C30"—C21	−165.2 (13)
C23—N2—C20—N1	10.5 (6)	C30—C31—C30"—C38"	112 (4)
C19—N2—C20—S1	−1.4 (5)	C32'—C31—C30"—C38"	−1.6 (12)
C23—N2—C20—S1	−170.8 (3)	C32—C31—C30"—C38"	14.8 (13)
C1—S1—C20—N1	176.1 (4)	C22—C21—C30"—C31	167.5 (9)
C1—S1—C20—N2	−2.7 (3)	N1—C21—C30"—C31	−27.0 (14)
C20—N1—C21—C22	−4.0 (7)	C30—C21—C30"—C31	63 (2)
C20—N1—C21—C30"	−169.3 (9)	C30'—C21—C30"—C31	94 (15)
C20—N1—C21—C30	161.5 (4)	C22—C21—C30"—C38"	−12.4 (9)
C20—N1—C21—C30'	−174.2 (8)	N1—C21—C30"—C38"	153.0 (14)
C30"—C21—C22—C23	154.1 (8)	C30—C21—C30"—C38"	−117 (2)
N1—C21—C22—C23	−10.3 (7)	C30'—C21—C30"—C38"	−86 (15)
C30—C21—C22—C23	−174.2 (4)	C31—C30"—C38"—C39"	147 (2)
C30'—C21—C22—C23	159.7 (8)	C21—C30"—C38"—C39"	−33 (2)
C30"—C21—C22—C41	−17.4 (10)	C30"—C38"—C39"—C40"	90.9 (18)
N1—C21—C22—C41	178.2 (5)	C38"—C39"—C40"—C41	−54 (3)
C30—C21—C22—C41	14.3 (8)	C39'—C40'—C41—C22	83.0 (15)
C30'—C21—C22—C41	−11.8 (10)	C39'—C40'—C41—C40	−17.8 (11)
C19—N2—C23—C22	169.2 (4)	C39'—C40'—C41—C40"	−33.2 (16)
C20—N2—C23—C22	−22.0 (5)	C21—C22—C41—C40'	−25.5 (11)
C19—N2—C23—C24	−68.9 (5)	C23—C22—C41—C40'	162.4 (9)
C20—N2—C23—C24	100.0 (5)	C21—C22—C41—C40	20.6 (9)
C21—C22—C23—N2	22.1 (6)	C23—C22—C41—C40	−151.5 (6)
C41—C22—C23—N2	−165.3 (4)	C21—C22—C41—C40"	70.0 (14)
C21—C22—C23—C24	−101.2 (5)	C23—C22—C41—C40"	−102.1 (14)
C41—C22—C23—C24	71.4 (5)	C39—C40—C41—C40'	25.2 (13)
N2—C23—C24—C29	−72.0 (6)	C39—C40—C41—C22	−76.0 (13)
C22—C23—C24—C29	50.2 (6)	C39—C40—C41—C40"	−177 (2)
N2—C23—C24—C25	111.4 (5)	C39"—C40"—C41—C40'	83 (2)
C22—C23—C24—C25	−126.4 (5)	C39"—C40"—C41—C22	−34 (3)
C29—C24—C25—C26	−1.4 (8)	C39"—C40"—C41—C40	69 (2)
C23—C24—C25—C26	175.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.86	2.43	2.952 (6)	120
N4—H4···O1ⁱⁱ	0.86	2.54	3.282 (5)	145

Symmetry codes: (i) y+1, −x+1, −z+2; (ii) −x+2, −y, z.

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