5-[4-Chloro-2-(4-chloro­benzyl­sulfan­yl)thia­zol-5-ylmethyl­ene]-3-(2,4-dichloro­benz­yl)thia­zolidine-2,4-dione

There are two mol­ecules in the asymmetric unit of the title compound, C₂₁H₁₂Cl₄N₂O₂S₃, which differ in the orientation of the chloro­benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.076
• wR factor = 0.221
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         13

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.111
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.75
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C2'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3'
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2'    in Main Residue .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O2'     ..       3.11 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3'   ..  O2      ..       3.16 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C21 H12 Cl4 N2 O2 S3

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.751
            Tmax scaled      0.260 Tmin scaled      0.178
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

5-[4-Chloro-2-(4-chlorobenzylsulfanyl)thiazol-5-ylmethylene]-3-(2,4- dichlorobenzyl)thiazolidine-2,4-dione

Crystal data

C21H12Cl4N2O2S3	Z = 4
Mr = 562.31	F(000) = 1136
Triclinic, P1	Dx = 1.636 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.0420 (7) Å	Cell parameters from 15 reflections
b = 14.359 (2) Å	θ = 12.8–23.6°
c = 21.2641 (15) Å	µ = 7.49 mm^−1
α = 100.386 (8)°	T = 293 K
β = 99.594 (7)°	Prism, yellow
γ = 104.237 (10)°	0.27 × 0.24 × 0.18 mm
V = 2283.0 (4) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	3186 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.111
Graphite monochromator	θmax = 70.8°, θmin = 2.2°
Nonprofiled ω scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
Tmin = 0.237, Tmax = 0.346	l = −26→25
9143 measured reflections	3 standard reflections every 120 min
8769 independent reflections	intensity decay: −14%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.221	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 1.0407P] where P = (Fo^2 + 2Fc^2)/3
8769 reflections	(Δ/σ)max = 0.012
577 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

Experimental. Spectroscopic analysis: νIR (cm-1)(CO):1739, 1679; 1H-NMR (CDCl3, 400 MHz, δ, p.p.m.): 4.48 (s, 2H, S—CH2), 4.99 (s, 2H, N—CH2), 7.16 (d, 1H, 2''-H), 7.22 (dd, 1H, 3''-H), 7.31 (d, 2H,2',6'-H),7.35 (d, 2H, 3',5'-H), 7.41(d, 1H, 5''-H), 8.03 (s, 1H, H—C═C).

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 (Ų)

	x	y	z	Uiso*/Ueq
S2	0.0495 (3)	0.15695 (17)	0.40492 (11)	0.0518 (6)
S1'	−0.2860 (3)	0.53137 (18)	0.56354 (11)	0.0545 (7)
S3'	−0.1692 (3)	0.33630 (18)	0.29760 (11)	0.0568 (7)
Cl3'	−0.5312 (3)	0.10816 (17)	0.42955 (11)	0.0552 (6)
S2'	−0.2544 (3)	0.39635 (17)	0.42791 (11)	0.0488 (6)
S1	0.0481 (3)	0.29483 (18)	0.54350 (11)	0.0563 (7)
Cl2'	−0.5598 (3)	0.54508 (18)	0.86087 (11)	0.0604 (7)
Cl2	−0.1912 (3)	0.3199 (2)	0.84627 (12)	0.0677 (8)
S3	0.1275 (3)	0.08479 (18)	0.27410 (12)	0.0592 (7)
Cl3	−0.3067 (3)	−0.11438 (18)	0.39718 (12)	0.0666 (8)
Cl1	0.4679 (4)	0.3150 (2)	0.93491 (13)	0.0933 (10)
Cl1'	0.1191 (4)	0.6053 (3)	0.96624 (13)	0.1019 (12)
Cl4'	−0.8824 (4)	0.1699 (2)	0.02897 (14)	0.1004 (11)
Cl4	0.7011 (4)	−0.0388 (2)	0.10048 (14)	0.0947 (10)
N1'	−0.4106 (9)	0.5087 (5)	0.6667 (3)	0.0448 (18)
N2'	−0.3566 (9)	0.2153 (5)	0.3613 (3)	0.0492 (19)
O2'	−0.5094 (8)	0.3398 (5)	0.6500 (3)	0.0631 (19)
O1'	−0.2981 (8)	0.6699 (5)	0.6631 (3)	0.0633 (19)
N1	−0.0775 (10)	0.2763 (6)	0.6473 (3)	0.053 (2)
O2	−0.2361 (8)	0.1138 (5)	0.6218 (3)	0.068 (2)
N2	−0.0955 (9)	−0.0171 (6)	0.3338 (3)	0.054 (2)
C13'	−0.4131 (10)	0.2190 (6)	0.4173 (4)	0.039 (2)
O1	0.0880 (9)	0.4321 (5)	0.6510 (3)	0.082 (2)
C6	0.0293 (10)	0.2951 (6)	0.7652 (4)	0.044 (2)
C12'	−0.3739 (10)	0.3073 (7)	0.4613 (4)	0.047 (2)
C12	−0.0970 (10)	0.0741 (6)	0.4348 (4)	0.038 (2)
C11	−0.1354 (11)	0.0957 (7)	0.4983 (4)	0.054 (3)
H11	−0.2060	0.0420	0.5092	0.065*
C9	−0.0879 (11)	0.1788 (6)	0.5441 (4)	0.046 (2)
C1	0.0059 (11)	0.3096 (6)	0.8290 (4)	0.045 (2)
C14'	−0.2692 (10)	0.3043 (6)	0.3596 (4)	0.045 (2)
C7'	−0.4621 (11)	0.5279 (7)	0.7298 (3)	0.048 (2)
H7'1	−0.5579	0.4721	0.7307	0.057*
H7'2	−0.5052	0.5856	0.7334	0.057*
C16	0.2488 (12)	−0.0475 (6)	0.1989 (4)	0.049 (2)
C1'	−0.3501 (11)	0.5521 (6)	0.8489 (4)	0.046 (2)
C6'	−0.3134 (11)	0.5447 (6)	0.7881 (4)	0.042 (2)
C13	−0.1593 (11)	−0.0128 (7)	0.3890 (4)	0.050 (2)
C8'	−0.4460 (11)	0.4100 (7)	0.6321 (4)	0.044 (2)
C4'	−0.0063 (12)	0.5732 (7)	0.8367 (4)	0.061 (3)
H4'	0.1093	0.5811	0.8324	0.074*
C2'	−0.2185 (14)	0.5710 (7)	0.9041 (5)	0.067 (3)
H2'	−0.2443	0.5764	0.9454	0.081*
C10'	−0.3277 (12)	0.5843 (8)	0.6398 (4)	0.057 (3)
C11'	−0.4206 (10)	0.3252 (6)	0.5240 (4)	0.044 (2)
H11'	−0.4868	0.2698	0.5347	0.053*
C21'	−0.5565 (12)	0.2094 (6)	0.2011 (4)	0.053 (3)
H21'	−0.5659	0.2142	0.2445	0.063*
C19	0.5250 (14)	−0.0467 (7)	0.1383 (5)	0.063 (3)
C8	−0.1392 (12)	0.1823 (8)	0.6072 (5)	0.058 (3)
C5'	−0.1446 (11)	0.5521 (6)	0.7825 (4)	0.053 (3)
H5'	−0.1209	0.5427	0.7409	0.063*
C9'	−0.3823 (10)	0.4099 (6)	0.5689 (4)	0.038 (2)
C15'	−0.2391 (11)	0.2201 (6)	0.2374 (4)	0.056 (3)
H15A	−0.1425	0.2131	0.2168	0.067*
H15B	−0.2664	0.1667	0.2596	0.067*
C2	0.1381 (13)	0.3106 (6)	0.8806 (5)	0.058 (3)
H2	0.1192	0.3173	0.9230	0.070*
C20	0.5451 (13)	−0.0427 (7)	0.2038 (4)	0.061 (3)
H20	0.6545	−0.0401	0.2279	0.074*
C16'	−0.3974 (13)	0.2108 (6)	0.1851 (4)	0.055 (3)
C21	0.4124 (13)	−0.0424 (7)	0.2346 (5)	0.058 (3)
H21	0.4303	−0.0389	0.2794	0.070*
C14	0.0149 (12)	0.0666 (7)	0.3338 (4)	0.055 (3)
C20'	−0.7030 (13)	0.2008 (6)	0.1533 (5)	0.062 (3)
H20'	−0.8073	0.2049	0.1655	0.074*
C18	0.3612 (14)	−0.0508 (7)	0.1025 (5)	0.065 (3)
H18	0.3456	−0.0524	0.0579	0.078*
C7	−0.1141 (11)	0.3000 (7)	0.7112 (4)	0.056 (3)
H7A	−0.2243	0.2544	0.7123	0.067*
H7B	−0.1280	0.3661	0.7192	0.067*
C10	0.0196 (14)	0.3460 (9)	0.6234 (5)	0.067 (3)
C3'	−0.0499 (12)	0.5817 (7)	0.8971 (4)	0.056 (3)
C17'	−0.3881 (13)	0.1995 (7)	0.1204 (4)	0.061 (3)
H17'	−0.2820	0.1995	0.1085	0.074*
C3	0.2952 (12)	0.3017 (7)	0.8688 (4)	0.056 (3)
C5	0.1889 (12)	0.2823 (6)	0.7551 (4)	0.052 (2)
H5	0.2065	0.2702	0.7126	0.062*
C19'	−0.6962 (15)	0.1860 (8)	0.0867 (5)	0.071 (3)
C15	0.0985 (12)	−0.0412 (6)	0.2326 (5)	0.067 (3)
H15C	0.0944	−0.0825	0.2640	0.080*
H15D	−0.0121	−0.0654	0.2003	0.080*
C4	0.3224 (13)	0.2871 (7)	0.8068 (4)	0.064 (3)
H4	0.4300	0.2804	0.7992	0.077*
C17	0.2238 (13)	−0.0527 (7)	0.1321 (4)	0.065 (3)
H17	0.1135	−0.0574	0.1077	0.077*
C18'	−0.5361 (15)	0.1881 (7)	0.0730 (5)	0.067 (3)
H18'	−0.5260	0.1815	0.0296	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0522 (15)	0.0487 (15)	0.0524 (15)	0.0088 (12)	0.0175 (12)	0.0089 (12)
S1'	0.0673 (17)	0.0528 (16)	0.0406 (14)	0.0097 (13)	0.0135 (12)	0.0126 (12)
S3'	0.0587 (16)	0.0590 (17)	0.0449 (14)	0.0018 (13)	0.0172 (12)	0.0076 (13)
Cl3'	0.0543 (14)	0.0528 (15)	0.0536 (15)	0.0085 (12)	0.0084 (11)	0.0129 (12)
S2'	0.0537 (15)	0.0485 (15)	0.0389 (13)	0.0060 (12)	0.0081 (11)	0.0110 (12)
S1	0.0637 (17)	0.0532 (16)	0.0464 (15)	0.0075 (13)	0.0073 (12)	0.0148 (12)
Cl2'	0.0619 (16)	0.0712 (18)	0.0559 (15)	0.0245 (14)	0.0302 (12)	0.0111 (13)
Cl2	0.0618 (16)	0.083 (2)	0.0602 (16)	0.0240 (15)	0.0231 (13)	0.0073 (14)
S3	0.0768 (19)	0.0528 (17)	0.0517 (15)	0.0154 (14)	0.0296 (14)	0.0115 (13)
Cl3	0.0662 (17)	0.0551 (16)	0.0680 (17)	−0.0040 (13)	0.0222 (14)	0.0109 (14)
Cl1	0.073 (2)	0.132 (3)	0.0682 (19)	0.0209 (19)	−0.0100 (15)	0.0419 (19)
Cl1'	0.069 (2)	0.160 (3)	0.0603 (19)	0.011 (2)	−0.0088 (15)	0.036 (2)
Cl4'	0.106 (3)	0.110 (3)	0.0633 (19)	0.025 (2)	−0.0186 (17)	0.0086 (18)
Cl4	0.083 (2)	0.114 (3)	0.086 (2)	0.0312 (19)	0.0386 (18)	−0.0025 (19)
N1'	0.048 (5)	0.050 (5)	0.036 (4)	0.017 (4)	0.001 (3)	0.015 (4)
N2'	0.046 (5)	0.047 (5)	0.048 (5)	0.000 (4)	0.022 (4)	0.002 (4)
O2'	0.082 (5)	0.053 (4)	0.043 (4)	0.001 (4)	0.014 (3)	0.009 (3)
O1'	0.078 (5)	0.044 (4)	0.068 (5)	0.019 (4)	0.011 (4)	0.014 (4)
N1	0.067 (5)	0.066 (6)	0.022 (4)	0.023 (5)	0.005 (4)	−0.001 (4)
O2	0.065 (5)	0.068 (5)	0.058 (4)	−0.001 (4)	0.017 (4)	0.007 (4)
N2	0.052 (5)	0.066 (6)	0.043 (4)	0.008 (4)	0.006 (4)	0.023 (4)
C13'	0.031 (5)	0.050 (6)	0.040 (5)	0.016 (4)	0.008 (4)	0.010 (4)
O1	0.103 (6)	0.037 (4)	0.081 (5)	−0.012 (4)	0.008 (4)	0.011 (4)
C6	0.029 (5)	0.063 (6)	0.039 (5)	0.020 (5)	−0.004 (4)	0.008 (5)
C12'	0.028 (5)	0.069 (7)	0.052 (6)	0.013 (5)	0.013 (4)	0.033 (5)
C12	0.034 (5)	0.038 (5)	0.041 (5)	0.009 (4)	0.001 (4)	0.012 (4)
C11	0.062 (6)	0.055 (7)	0.036 (5)	0.013 (5)	−0.001 (5)	0.003 (5)
C9	0.060 (6)	0.042 (6)	0.037 (5)	0.018 (5)	0.004 (4)	0.012 (4)
C1	0.040 (5)	0.049 (6)	0.040 (5)	0.008 (4)	0.003 (4)	0.009 (4)
C14'	0.037 (5)	0.046 (6)	0.043 (5)	−0.002 (4)	0.003 (4)	0.014 (5)
C7'	0.060 (6)	0.067 (7)	0.028 (5)	0.034 (5)	0.014 (4)	0.016 (5)
C16	0.056 (6)	0.047 (6)	0.050 (6)	0.018 (5)	0.014 (5)	0.016 (5)
C1'	0.051 (6)	0.033 (5)	0.057 (6)	0.012 (4)	0.020 (5)	0.011 (5)
C6'	0.040 (5)	0.050 (6)	0.040 (5)	0.019 (4)	0.007 (4)	0.015 (4)
C13	0.048 (6)	0.052 (6)	0.045 (5)	−0.003 (5)	0.011 (4)	0.025 (5)
C8'	0.032 (5)	0.060 (7)	0.040 (5)	0.017 (5)	0.007 (4)	0.010 (5)
C4'	0.048 (6)	0.097 (9)	0.044 (6)	0.025 (6)	0.004 (5)	0.030 (6)
C2'	0.080 (8)	0.069 (7)	0.048 (6)	0.011 (6)	0.020 (6)	0.010 (5)
C10'	0.057 (6)	0.075 (8)	0.039 (6)	0.021 (6)	0.004 (5)	0.016 (6)
C11'	0.035 (5)	0.048 (6)	0.043 (5)	−0.002 (4)	0.003 (4)	0.016 (5)
C21'	0.070 (7)	0.051 (6)	0.028 (5)	0.003 (5)	0.006 (5)	0.009 (4)
C19	0.089 (8)	0.072 (7)	0.047 (6)	0.053 (6)	0.024 (6)	0.012 (5)
C8	0.053 (6)	0.060 (7)	0.042 (6)	0.000 (5)	−0.008 (5)	0.002 (5)
C5'	0.053 (6)	0.073 (7)	0.039 (5)	0.021 (5)	0.020 (5)	0.014 (5)
C9'	0.028 (4)	0.041 (5)	0.036 (5)	−0.001 (4)	−0.003 (4)	0.006 (4)
C15'	0.072 (7)	0.057 (6)	0.042 (5)	0.035 (5)	0.012 (5)	−0.004 (5)
C2	0.069 (7)	0.036 (5)	0.058 (6)	−0.014 (5)	0.018 (5)	0.019 (5)
C20	0.072 (7)	0.072 (7)	0.039 (6)	0.021 (6)	0.010 (5)	0.010 (5)
C16'	0.076 (7)	0.035 (5)	0.050 (6)	0.001 (5)	0.026 (5)	0.012 (5)
C21	0.065 (7)	0.071 (7)	0.045 (6)	0.034 (6)	0.012 (5)	0.009 (5)
C14	0.065 (7)	0.062 (7)	0.047 (6)	0.021 (6)	0.020 (5)	0.024 (5)
C20'	0.061 (7)	0.051 (7)	0.068 (7)	0.004 (5)	0.018 (6)	0.014 (6)
C18	0.095 (9)	0.062 (7)	0.058 (7)	0.048 (6)	0.020 (6)	0.023 (5)
C7	0.040 (6)	0.058 (7)	0.066 (7)	0.020 (5)	0.004 (5)	0.005 (5)
C10	0.071 (7)	0.072 (8)	0.040 (6)	0.006 (6)	−0.014 (5)	0.019 (6)
C3'	0.045 (6)	0.072 (7)	0.046 (6)	0.019 (5)	−0.012 (5)	0.017 (5)
C17'	0.078 (8)	0.064 (7)	0.038 (6)	0.015 (6)	0.007 (5)	0.014 (5)
C3	0.049 (6)	0.071 (7)	0.048 (6)	0.012 (5)	0.000 (5)	0.028 (5)
C5	0.066 (7)	0.040 (6)	0.045 (6)	0.018 (5)	0.010 (5)	0.001 (4)
C19'	0.091 (9)	0.072 (8)	0.046 (6)	0.033 (7)	−0.003 (6)	0.006 (6)
C15	0.074 (7)	0.046 (6)	0.069 (7)	0.008 (5)	0.019 (6)	−0.006 (5)
C4	0.059 (7)	0.085 (8)	0.039 (6)	0.004 (6)	0.004 (5)	0.018 (6)
C17	0.062 (7)	0.084 (8)	0.046 (6)	0.033 (6)	0.007 (5)	0.000 (6)
C18'	0.104 (9)	0.058 (7)	0.042 (6)	0.027 (7)	0.018 (6)	0.007 (5)

Geometric parameters (Å, º)

S2—C12	1.742 (8)	C7'—H7'2	0.9700
S2—C14	1.738 (9)	C16—C21	1.383 (11)
S1'—C9'	1.757 (8)	C16—C17	1.388 (11)
S1'—C10'	1.785 (10)	C16—C15	1.516 (11)
S3'—C14'	1.728 (8)	C1'—C6'	1.365 (10)
S3'—C15'	1.806 (8)	C1'—C2'	1.379 (11)
Cl3'—C13'	1.729 (9)	C6'—C5'	1.363 (10)
S2'—C12'	1.736 (8)	C8'—C9'	1.514 (11)
S2'—C14'	1.744 (9)	C4'—C5'	1.392 (10)
S1—C9	1.756 (9)	C4'—C3'	1.379 (11)
S1—C10	1.800 (10)	C4'—H4'	0.9300
Cl2'—C1'	1.729 (8)	C2'—C3'	1.363 (11)
Cl2—C1	1.721 (8)	C2'—H2'	0.9300
S3—C14	1.700 (9)	C11'—C9'	1.338 (10)
S3—C15	1.804 (8)	C11'—H11'	0.9300
Cl3—C13	1.695 (8)	C21'—C16'	1.375 (11)
Cl1—C3	1.749 (9)	C21'—C20'	1.386 (11)
Cl1'—C3'	1.746 (8)	C21'—H21'	0.9300
Cl4'—C19'	1.707 (10)	C19—C18	1.389 (12)
Cl4—C19	1.732 (10)	C19—C20	1.363 (11)
N1'—C10'	1.394 (11)	C5'—H5'	0.9300
N1'—C8'	1.408 (10)	C15'—C16'	1.506 (12)
N1'—C7'	1.468 (9)	C15'—H15A	0.9700
N2'—C14'	1.308 (9)	C15'—H15B	0.9700
N2'—C13'	1.340 (9)	C2—C3	1.360 (11)
O2'—C8'	1.173 (10)	C2—H2	0.9300
O1'—C10'	1.187 (10)	C20—C21	1.343 (11)
N1—C10	1.342 (11)	C20—H20	0.9300
N1—C8	1.381 (11)	C16'—C17'	1.373 (11)
N1—C7	1.437 (10)	C21—H21	0.9300
O2—C8	1.218 (10)	C20'—C19'	1.407 (12)
N2—C14	1.305 (10)	C20'—H20'	0.9300
N2—C13	1.355 (10)	C18—C17	1.357 (11)
C13'—C12'	1.363 (11)	C18—H18	0.9300
O1—C10	1.213 (11)	C7—H7A	0.9700
C6—C5	1.385 (10)	C7—H7B	0.9700
C6—C1	1.387 (11)	C17'—C18'	1.379 (12)
C6—C7	1.510 (10)	C17'—H17'	0.9300
C12'—C11'	1.439 (11)	C3—C4	1.362 (11)
C12—C13	1.359 (10)	C5—C4	1.381 (11)
C12—C11	1.432 (10)	C5—H5	0.9300
C11—C9	1.324 (10)	C19'—C18'	1.361 (13)
C11—H11	0.9300	C15—H15C	0.9700
C9—C8	1.464 (12)	C15—H15D	0.9700
C1—C2	1.391 (11)	C4—H4	0.9300
C7'—C6'	1.511 (10)	C17—H17	0.9300
C7'—H7'1	0.9700	C18'—H18'	0.9300
C12—S2—C14	89.8 (4)	C20—C19—Cl4	121.6 (8)
C9'—S1'—C10'	93.1 (5)	O2—C8—N1	122.7 (9)
C14'—S3'—C15'	101.5 (4)	O2—C8—C9	125.2 (9)
C12'—S2'—C14'	89.3 (4)	N1—C8—C9	111.8 (9)
C9—S1—C10	90.5 (5)	C6'—C5'—C4'	122.5 (8)
C14—S3—C15	100.7 (5)	C6'—C5'—H5'	118.7
C10'—N1'—C8'	118.8 (8)	C4'—C5'—H5'	118.7
C10'—N1'—C7'	122.5 (8)	C11'—C9'—C8'	119.6 (8)
C8'—N1'—C7'	118.7 (7)	C11'—C9'—S1'	129.4 (7)
C14'—N2'—C13'	109.2 (7)	C8'—C9'—S1'	110.5 (6)
C10—N1—C8	116.3 (8)	C16'—C15'—S3'	113.4 (6)
C10—N1—C7	120.9 (8)	C16'—C15'—H15A	108.9
C8—N1—C7	122.8 (9)	S3'—C15'—H15A	108.9
C14—N2—C13	112.2 (8)	C16'—C15'—H15B	108.9
N2'—C13'—C12'	119.6 (8)	S3'—C15'—H15B	108.9
N2'—C13'—Cl3'	116.6 (7)	H15A—C15'—H15B	107.7
C12'—C13'—Cl3'	123.8 (7)	C3—C2—C1	119.6 (9)
C5—C6—C1	117.5 (8)	C3—C2—H2	120.2
C5—C6—C7	123.5 (8)	C1—C2—H2	120.2
C1—C6—C7	118.9 (8)	C21—C20—C19	122.3 (10)
C13'—C12'—C11'	127.4 (8)	C21—C20—H20	118.9
C13'—C12'—S2'	107.0 (6)	C19—C20—H20	118.9
C11'—C12'—S2'	125.6 (7)	C21'—C16'—C17'	118.7 (10)
C13—C12—C11	127.5 (8)	C21'—C16'—C15'	120.2 (8)
C13—C12—S2	108.2 (6)	C17'—C16'—C15'	121.1 (9)
C11—C12—S2	124.2 (7)	C20—C21—C16	119.2 (9)
C9—C11—C12	131.3 (9)	C20—C21—H21	120.4
C9—C11—H11	114.4	C16—C21—H21	120.4
C12—C11—H11	114.4	N2—C14—S3	124.4 (7)
C11—C9—C8	121.4 (9)	N2—C14—S2	113.1 (7)
C11—C9—S1	128.5 (8)	S3—C14—S2	122.4 (6)
C8—C9—S1	110.0 (7)	C19'—C20'—C21'	121.0 (9)
C2—C1—C6	120.9 (8)	C19'—C20'—H20'	119.5
C2—C1—Cl2	117.9 (7)	C21'—C20'—H20'	119.5
C6—C1—Cl2	121.2 (7)	C19—C18—C17	120.4 (10)
N2'—C14'—S3'	126.1 (7)	C19—C18—H18	119.8
N2'—C14'—S2'	114.8 (6)	C17—C18—H18	119.8
S3'—C14'—S2'	119.0 (5)	N1—C7—C6	112.6 (7)
N1'—C7'—C6'	113.3 (7)	N1—C7—H7A	109.1
N1'—C7'—H7'1	108.9	C6—C7—H7A	109.1
C6'—C7'—H7'1	108.9	N1—C7—H7B	109.1
N1'—C7'—H7'2	108.9	C6—C7—H7B	109.1
C6'—C7'—H7'2	108.9	H7A—C7—H7B	107.8
H7'1—C7'—H7'2	107.7	O1—C10—N1	126.6 (10)
C21—C16—C17	119.8 (9)	O1—C10—S1	122.1 (9)
C21—C16—C15	120.8 (9)	N1—C10—S1	111.2 (8)
C17—C16—C15	119.3 (9)	C2'—C3'—C4'	122.4 (8)
C6'—C1'—C2'	121.0 (8)	C2'—C3'—Cl1'	119.7 (8)
C6'—C1'—Cl2'	121.9 (7)	C4'—C3'—Cl1'	117.9 (7)
C2'—C1'—Cl2'	117.0 (7)	C16'—C17'—C18'	120.1 (10)
C5'—C6'—C1'	118.7 (8)	C16'—C17'—H17'	120.0
C5'—C6'—C7'	122.7 (7)	C18'—C17'—H17'	120.0
C1'—C6'—C7'	118.6 (8)	C2—C3—C4	121.0 (9)
N2—C13—C12	116.6 (8)	C2—C3—Cl1	119.3 (8)
N2—C13—Cl3	118.9 (7)	C4—C3—Cl1	119.6 (8)
C12—C13—Cl3	124.5 (7)	C6—C5—C4	121.6 (9)
O2'—C8'—N1'	125.7 (8)	C6—C5—H5	119.2
O2'—C8'—C9'	125.7 (9)	C4—C5—H5	119.2
N1'—C8'—C9'	108.6 (8)	C18'—C19'—C20'	116.2 (10)
C5'—C4'—C3'	116.4 (8)	C18'—C19'—Cl4'	124.3 (9)
C5'—C4'—H4'	121.8	C20'—C19'—Cl4'	119.5 (9)
C3'—C4'—H4'	121.8	C16—C15—S3	110.3 (6)
C3'—C2'—C1'	118.8 (9)	C16—C15—H15C	109.6
C3'—C2'—H2'	120.6	S3—C15—H15C	109.6
C1'—C2'—H2'	120.6	C16—C15—H15D	109.6
O1'—C10'—N1'	124.7 (9)	S3—C15—H15D	109.6
O1'—C10'—S1'	126.1 (8)	H15C—C15—H15D	108.1
N1'—C10'—S1'	109.0 (7)	C3—C4—C5	119.4 (9)
C9'—C11'—C12'	129.3 (8)	C3—C4—H4	120.3
C9'—C11'—H11'	115.4	C5—C4—H4	120.3
C12'—C11'—H11'	115.4	C18—C17—C16	119.6 (9)
C16'—C21'—C20'	120.7 (8)	C18—C17—H17	120.2
C16'—C21'—H21'	119.7	C16—C17—H17	120.2
C20'—C21'—H21'	119.7	C19'—C18'—C17'	123.2 (10)
C18—C19—C20	118.6 (9)	C19'—C18'—H18'	118.4
C18—C19—Cl4	119.7 (8)	C17'—C18'—H18'	118.4
C14'—N2'—C13'—C12'	−0.5 (11)	C3'—C4'—C5'—C6'	3.0 (15)
C14'—N2'—C13'—Cl3'	−179.6 (6)	C12'—C11'—C9'—C8'	−179.6 (8)
N2'—C13'—C12'—C11'	−178.9 (8)	C12'—C11'—C9'—S1'	8.9 (14)
Cl3'—C13'—C12'—C11'	0.1 (12)	O2'—C8'—C9'—C11'	10.1 (14)
N2'—C13'—C12'—S2'	0.8 (9)	N1'—C8'—C9'—C11'	−171.9 (7)
Cl3'—C13'—C12'—S2'	179.9 (4)	O2'—C8'—C9'—S1'	−176.9 (8)
C14'—S2'—C12'—C13'	−0.7 (6)	N1'—C8'—C9'—S1'	1.1 (8)
C14'—S2'—C12'—C11'	179.1 (7)	C10'—S1'—C9'—C11'	171.1 (8)
C14—S2—C12—C13	−0.5 (7)	C10'—S1'—C9'—C8'	−1.0 (6)
C14—S2—C12—C11	177.0 (7)	C14'—S3'—C15'—C16'	96.8 (7)
C13—C12—C11—C9	−176.2 (9)	C6—C1—C2—C3	2.9 (14)
S2—C12—C11—C9	6.8 (14)	Cl2—C1—C2—C3	179.4 (7)
C12—C11—C9—C8	−177.8 (9)	C18—C19—C20—C21	−0.1 (15)
C12—C11—C9—S1	−1.8 (15)	Cl4—C19—C20—C21	175.7 (8)
C10—S1—C9—C11	179.6 (9)	C20'—C21'—C16'—C17'	−2.6 (14)
C10—S1—C9—C8	−4.0 (7)	C20'—C21'—C16'—C15'	180.0 (8)
C5—C6—C1—C2	−0.3 (14)	S3'—C15'—C16'—C21'	−64.3 (10)
C7—C6—C1—C2	−176.8 (8)	S3'—C15'—C16'—C17'	118.3 (9)
C5—C6—C1—Cl2	−176.7 (7)	C19—C20—C21—C16	0.7 (15)
C7—C6—C1—Cl2	6.9 (12)	C17—C16—C21—C20	0.0 (14)
C13'—N2'—C14'—S3'	179.2 (6)	C15—C16—C21—C20	−176.4 (9)
C13'—N2'—C14'—S2'	−0.1 (9)	C13—N2—C14—S3	176.5 (7)
C15'—S3'—C14'—N2'	5.7 (9)	C13—N2—C14—S2	1.1 (10)
C15'—S3'—C14'—S2'	−175.1 (5)	C15—S3—C14—N2	−15.5 (9)
C12'—S2'—C14'—N2'	0.4 (7)	C15—S3—C14—S2	159.5 (6)
C12'—S2'—C14'—S3'	−178.9 (5)	C12—S2—C14—N2	−0.3 (7)
C10'—N1'—C7'—C6'	−83.0 (10)	C12—S2—C14—S3	−175.8 (6)
C8'—N1'—C7'—C6'	96.8 (9)	C16'—C21'—C20'—C19'	4.7 (14)
C2'—C1'—C6'—C5'	2.9 (14)	C20—C19—C18—C17	−1.2 (15)
Cl2'—C1'—C6'—C5'	179.2 (7)	Cl4—C19—C18—C17	−177.1 (8)
C2'—C1'—C6'—C7'	−177.6 (8)	C10—N1—C7—C6	−86.1 (11)
Cl2'—C1'—C6'—C7'	−1.3 (12)	C8—N1—C7—C6	94.2 (10)
N1'—C7'—C6'—C5'	6.9 (12)	C5—C6—C7—N1	8.2 (13)
N1'—C7'—C6'—C1'	−172.6 (7)	C1—C6—C7—N1	−175.6 (8)
C14—N2—C13—C12	−1.6 (12)	C8—N1—C10—O1	−178.7 (10)
C14—N2—C13—Cl3	179.3 (7)	C7—N1—C10—O1	1.6 (16)
C11—C12—C13—N2	−176.1 (8)	C8—N1—C10—S1	−1.6 (11)
S2—C12—C13—N2	1.3 (10)	C7—N1—C10—S1	178.7 (6)
C11—C12—C13—Cl3	2.9 (14)	C9—S1—C10—O1	−179.5 (9)
S2—C12—C13—Cl3	−179.7 (5)	C9—S1—C10—N1	3.3 (7)
C10'—N1'—C8'—O2'	177.3 (9)	C1'—C2'—C3'—C4'	−0.8 (15)
C7'—N1'—C8'—O2'	−2.5 (13)	C1'—C2'—C3'—Cl1'	−179.7 (7)
C10'—N1'—C8'—C9'	−0.6 (10)	C5'—C4'—C3'—C2'	−0.5 (15)
C7'—N1'—C8'—C9'	179.5 (6)	C5'—C4'—C3'—Cl1'	178.5 (7)
C6'—C1'—C2'—C3'	−0.4 (14)	C21'—C16'—C17'—C18'	0.7 (14)
Cl2'—C1'—C2'—C3'	−177.0 (7)	C15'—C16'—C17'—C18'	178.1 (8)
C8'—N1'—C10'—O1'	176.6 (9)	C1—C2—C3—C4	−3.1 (15)
C7'—N1'—C10'—O1'	−3.5 (14)	C1—C2—C3—Cl1	173.8 (7)
C8'—N1'—C10'—S1'	−0.1 (9)	C1—C6—C5—C4	−2.2 (14)
C7'—N1'—C10'—S1'	179.7 (6)	C7—C6—C5—C4	174.1 (9)
C9'—S1'—C10'—O1'	−176.0 (9)	C21'—C20'—C19'—C18'	−4.7 (15)
C9'—S1'—C10'—N1'	0.6 (7)	C21'—C20'—C19'—Cl4'	176.9 (7)
C13'—C12'—C11'—C9'	178.7 (8)	C21—C16—C15—S3	76.3 (10)
S2'—C12'—C11'—C9'	−1.0 (13)	C17—C16—C15—S3	−100.1 (9)
C10—N1—C8—O2	−176.1 (9)	C14—S3—C15—C16	−153.9 (7)
C7—N1—C8—O2	3.7 (15)	C2—C3—C4—C5	0.7 (15)
C10—N1—C8—C9	−1.6 (12)	Cl1—C3—C4—C5	−176.3 (7)
C7—N1—C8—C9	178.2 (7)	C6—C5—C4—C3	2.0 (15)
C11—C9—C8—O2	−4.9 (16)	C19—C18—C17—C16	1.9 (15)
S1—C9—C8—O2	178.4 (9)	C21—C16—C17—C18	−1.3 (15)
C11—C9—C8—N1	−179.3 (8)	C15—C16—C17—C18	175.1 (9)
S1—C9—C8—N1	4.0 (10)	C20'—C19'—C18'—C17'	2.8 (16)
C1'—C6'—C5'—C4'	−4.2 (14)	Cl4'—C19'—C18'—C17'	−178.8 (8)
C7'—C6'—C5'—C4'	176.3 (9)	C16'—C17'—C18'—C19'	−0.9 (16)