A second polymorph of 1,2-bis­[4-(4-chloro­phen­yl)-1,3-thia­zol-2-yl]disulfane

The asymmetric unit of the title compound, C₁₈H₁₀Cl₂N₂S₄, consists of one full mol­ecule and two half mol­ecules, which are completed by twofold rotation symmetry.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.039
• wR factor = 0.123
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5493

Author Response: Since the compound was prepared in a project that ended some years ago, the meassurement was performed using the theta range that was routinely applied at that time. In view of the fact that the structure is an organic compound, which scatters with minor intensity at high theta values we feel that the presented structural information on this compound is reliable enough in order to unambigiously solve the structure and refine the structure model reliably.

PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      22.98 Deg.

Author Response: see vrf_THETM01_Har62

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      22.98 Deg.

Author Response: see vrf_THETM01_Har62

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S4     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S5     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S7     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C18 H10 Cl2 N2 S4

   3 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,2-bis[4-(p-chlorophenyl)-1,3-thiazol-2-yl]disulfane

Crystal data

C18H10Cl2N2S4	Dx = 1.580 Mg m^−3
Mr = 453.44	Melting point: 430 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.293 (3) Å	Cell parameters from 25 reflections
b = 9.999 (3) Å	θ = 4.3–12.3°
c = 37.594 (3) Å	µ = 0.78 mm^−1
β = 91.53 (1)°	T = 299 K
V = 7625 (3) Å^3	Needle, colourless
Z = 16	0.55 × 0.22 × 0.05 mm
F(000) = 3680

Data collection

Enraf–Nonius CAD-4 diffractometer	3152 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 23.0°, θmin = 1.1°
ω/2θ scans	h = −22→6
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.696, Tmax = 0.965	l = −41→41
7300 measured reflections	3 standard reflections every 120 min
5282 independent reflections	intensity decay: 3.1%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.057P)^2 + 7.2189P] where P = (Fo^2 + 2Fc^2)/3
5282 reflections	(Δ/σ)max = 0.005
469 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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
C2	0.23621 (19)	0.5095 (4)	0.30600 (10)	0.0481 (11)
C4	0.21253 (19)	0.3816 (5)	0.35206 (10)	0.0466 (11)
C5	0.2634 (2)	0.3099 (5)	0.33867 (11)	0.0593 (12)
H5	0.2791	0.2300	0.3483	0.071*
C6	0.1762 (2)	0.3493 (4)	0.38414 (11)	0.0498 (11)
C7	0.13737 (19)	0.4463 (5)	0.40022 (11)	0.0537 (12)
H7	0.1346	0.5318	0.3906	0.064*
C8	0.1031 (2)	0.4156 (5)	0.43042 (12)	0.0608 (13)
H8	0.0767	0.4799	0.4408	0.073*
C9	0.1080 (2)	0.2909 (6)	0.44494 (12)	0.0641 (13)
C10	0.1471 (3)	0.1945 (5)	0.43014 (13)	0.0749 (15)
H10	0.1507	0.1100	0.4404	0.090*
C11	0.1810 (2)	0.2255 (5)	0.39995 (13)	0.0666 (13)
H11	0.2078	0.1609	0.3900	0.080*
C12	0.27528 (19)	0.5296 (4)	0.21004 (11)	0.0499 (11)
C14	0.2774 (2)	0.4309 (4)	0.15766 (12)	0.0494 (11)
C15	0.2116 (2)	0.4252 (5)	0.16358 (12)	0.0587 (12)
H15	0.1808	0.3872	0.1478	0.070*
C16	0.3120 (2)	0.3813 (4)	0.12632 (11)	0.0484 (11)
C17	0.2796 (2)	0.3591 (5)	0.09377 (12)	0.0634 (13)
H17	0.2342	0.3703	0.0919	0.076*
C18	0.3137 (3)	0.3206 (5)	0.06418 (13)	0.0697 (14)
H18	0.2915	0.3044	0.0427	0.084*
C19	0.3805 (3)	0.3066 (5)	0.06697 (13)	0.0653 (13)
C20	0.4139 (2)	0.3235 (5)	0.09880 (13)	0.0646 (13)
H20	0.4592	0.3096	0.1004	0.078*
C21	0.3799 (2)	0.3612 (5)	0.12842 (12)	0.0563 (12)
H21	0.4026	0.3734	0.1500	0.068*
C22	−0.0157 (2)	−0.2194 (5)	0.29745 (12)	0.0630 (13)
C24	−0.0281 (2)	−0.3492 (5)	0.34423 (12)	0.0531 (12)
C25	0.0279 (2)	−0.4031 (5)	0.33132 (12)	0.0660 (14)
H25	0.0503	−0.4750	0.3416	0.079*
C26	−0.0619 (2)	−0.3890 (5)	0.37662 (11)	0.0543 (12)
C27	−0.0532 (2)	−0.5141 (5)	0.39174 (14)	0.0669 (14)
H27	−0.0254	−0.5754	0.3812	0.080*
C28	−0.0853 (3)	−0.5490 (6)	0.42218 (14)	0.0758 (15)
H28	−0.0793	−0.6338	0.4319	0.091*
C29	−0.1258 (2)	−0.4593 (6)	0.43822 (13)	0.0673 (14)
C30	−0.1351 (2)	−0.3334 (6)	0.42400 (13)	0.0672 (14)
H30	−0.1628	−0.2726	0.4348	0.081*
C31	−0.1027 (2)	−0.2989 (5)	0.39362 (12)	0.0601 (12)
H31	−0.1082	−0.2134	0.3843	0.072*
C32	0.52153 (19)	0.2338 (4)	0.70055 (10)	0.0464 (11)
C34	0.5359 (2)	0.3393 (4)	0.65003 (11)	0.0495 (11)
C35	0.4702 (2)	0.3569 (5)	0.65346 (13)	0.0726 (15)
H35	0.4436	0.4027	0.6371	0.087*
C36	0.5761 (2)	0.3837 (4)	0.62026 (11)	0.0507 (11)
C37	0.5468 (2)	0.4209 (5)	0.58790 (12)	0.0613 (13)
H37	0.5011	0.4196	0.5853	0.074*
C38	0.5842 (3)	0.4596 (5)	0.55974 (13)	0.0720 (15)
H38	0.5642	0.4843	0.5382	0.086*
C39	0.6517 (3)	0.4612 (5)	0.56399 (13)	0.0669 (14)
C40	0.6820 (2)	0.4259 (5)	0.59541 (13)	0.0594 (12)
H40	0.7278	0.4273	0.5977	0.071*
C41	0.6441 (2)	0.3881 (4)	0.62384 (11)	0.0543 (11)
H41	0.6646	0.3656	0.6455	0.065*
N3	0.19706 (15)	0.4963 (4)	0.33278 (9)	0.0491 (9)
N13	0.31345 (15)	0.4908 (4)	0.18487 (9)	0.0481 (9)
N23	−0.05268 (17)	−0.2434 (4)	0.32436 (10)	0.0612 (10)
N33	0.56512 (15)	0.2667 (3)	0.67752 (9)	0.0463 (9)
S1	0.29449 (6)	0.38522 (13)	0.30202 (3)	0.0637 (4)
S2	0.22901 (6)	0.64708 (13)	0.27738 (3)	0.0629 (4)
S3	0.30801 (6)	0.62241 (14)	0.24611 (3)	0.0617 (4)
S4	0.19239 (5)	0.49524 (13)	0.20293 (3)	0.0625 (4)
S5	0.05192 (6)	−0.32252 (15)	0.29385 (3)	0.0715 (4)
S6	−0.03809 (8)	−0.09363 (15)	0.26688 (4)	0.0874 (5)
S7	0.44198 (5)	0.28546 (15)	0.69124 (4)	0.0726 (4)
S8	0.54226 (5)	0.12598 (13)	0.73614 (3)	0.0564 (3)
Cl1	0.06298 (7)	0.25013 (18)	0.48215 (4)	0.0941 (5)
Cl2	0.42503 (8)	0.26578 (17)	0.02928 (4)	0.0997 (5)
Cl3	−0.16723 (8)	−0.50437 (18)	0.47611 (4)	0.0983 (5)
Cl4	0.70001 (8)	0.50883 (18)	0.52844 (4)	0.0993 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.046 (2)	0.055 (3)	0.044 (3)	−0.001 (2)	0.006 (2)	−0.010 (2)
C4	0.045 (2)	0.052 (3)	0.043 (2)	−0.005 (2)	0.0014 (19)	−0.008 (2)
C5	0.067 (3)	0.054 (3)	0.057 (3)	0.010 (2)	0.010 (2)	−0.004 (2)
C6	0.048 (2)	0.053 (3)	0.048 (3)	−0.003 (2)	0.001 (2)	−0.004 (2)
C7	0.044 (2)	0.067 (3)	0.050 (3)	0.002 (2)	0.003 (2)	0.002 (2)
C8	0.056 (3)	0.073 (4)	0.054 (3)	0.005 (3)	0.009 (2)	−0.005 (3)
C9	0.057 (3)	0.083 (4)	0.052 (3)	−0.018 (3)	0.006 (2)	0.002 (3)
C10	0.095 (4)	0.060 (3)	0.070 (4)	−0.010 (3)	0.011 (3)	0.003 (3)
C11	0.082 (3)	0.052 (3)	0.067 (3)	0.001 (3)	0.017 (3)	0.002 (3)
C12	0.037 (2)	0.052 (3)	0.061 (3)	−0.003 (2)	0.009 (2)	0.010 (2)
C14	0.045 (2)	0.047 (3)	0.057 (3)	−0.005 (2)	0.005 (2)	0.007 (2)
C15	0.042 (2)	0.063 (3)	0.071 (3)	−0.012 (2)	0.001 (2)	−0.001 (3)
C16	0.050 (3)	0.044 (3)	0.052 (3)	−0.005 (2)	0.006 (2)	0.008 (2)
C17	0.052 (3)	0.076 (4)	0.063 (3)	−0.006 (3)	0.000 (2)	0.002 (3)
C18	0.078 (4)	0.074 (4)	0.057 (3)	−0.009 (3)	−0.003 (3)	−0.005 (3)
C19	0.076 (4)	0.055 (3)	0.065 (3)	−0.004 (3)	0.013 (3)	0.002 (3)
C20	0.056 (3)	0.067 (3)	0.072 (3)	0.010 (2)	0.010 (3)	0.007 (3)
C21	0.051 (3)	0.061 (3)	0.057 (3)	0.006 (2)	0.003 (2)	0.004 (2)
C22	0.055 (3)	0.069 (3)	0.067 (3)	0.002 (2)	0.019 (2)	−0.013 (3)
C24	0.042 (2)	0.063 (3)	0.055 (3)	0.003 (2)	−0.002 (2)	−0.019 (3)
C25	0.057 (3)	0.082 (4)	0.059 (3)	0.016 (3)	−0.006 (2)	−0.022 (3)
C26	0.045 (2)	0.065 (3)	0.053 (3)	−0.002 (2)	−0.006 (2)	−0.013 (3)
C27	0.062 (3)	0.065 (4)	0.074 (4)	0.007 (3)	−0.005 (3)	−0.007 (3)
C28	0.083 (4)	0.067 (4)	0.076 (4)	−0.004 (3)	−0.012 (3)	0.003 (3)
C29	0.061 (3)	0.083 (4)	0.058 (3)	−0.011 (3)	−0.005 (2)	0.000 (3)
C30	0.061 (3)	0.078 (4)	0.063 (3)	0.000 (3)	0.006 (3)	−0.006 (3)
C31	0.055 (3)	0.065 (3)	0.062 (3)	0.006 (3)	0.005 (2)	−0.007 (3)
C32	0.040 (2)	0.059 (3)	0.040 (2)	0.001 (2)	0.0033 (19)	−0.008 (2)
C34	0.047 (3)	0.054 (3)	0.048 (3)	0.010 (2)	0.005 (2)	−0.003 (2)
C35	0.049 (3)	0.094 (4)	0.076 (3)	0.017 (3)	0.006 (2)	0.023 (3)
C36	0.048 (3)	0.053 (3)	0.051 (3)	0.004 (2)	0.003 (2)	−0.006 (2)
C37	0.054 (3)	0.074 (3)	0.057 (3)	0.006 (2)	0.001 (2)	0.000 (3)
C38	0.077 (4)	0.082 (4)	0.057 (3)	0.013 (3)	0.007 (3)	0.006 (3)
C39	0.082 (4)	0.058 (3)	0.062 (3)	−0.003 (3)	0.024 (3)	−0.003 (3)
C40	0.054 (3)	0.058 (3)	0.067 (3)	−0.005 (2)	0.013 (2)	−0.007 (3)
C41	0.052 (3)	0.058 (3)	0.053 (3)	−0.003 (2)	0.004 (2)	−0.005 (2)
N3	0.0416 (19)	0.053 (2)	0.053 (2)	0.0007 (17)	0.0089 (17)	−0.002 (2)
N13	0.0369 (18)	0.055 (2)	0.052 (2)	−0.0030 (17)	0.0052 (17)	0.0033 (19)
N23	0.050 (2)	0.067 (3)	0.067 (3)	0.005 (2)	0.015 (2)	−0.007 (2)
N33	0.0360 (18)	0.056 (2)	0.047 (2)	0.0015 (17)	0.0061 (16)	−0.0043 (18)
S1	0.0606 (7)	0.0703 (9)	0.0610 (8)	0.0150 (6)	0.0192 (6)	−0.0071 (7)
S2	0.0601 (7)	0.0636 (9)	0.0664 (8)	0.0067 (6)	0.0265 (6)	0.0051 (7)
S3	0.0492 (6)	0.0779 (9)	0.0590 (7)	−0.0133 (6)	0.0177 (5)	−0.0070 (7)
S4	0.0391 (6)	0.0745 (9)	0.0745 (8)	−0.0071 (6)	0.0155 (5)	0.0060 (7)
S5	0.0476 (7)	0.0974 (11)	0.0700 (8)	0.0079 (7)	0.0116 (6)	−0.0276 (8)
S6	0.0915 (10)	0.0767 (10)	0.0966 (11)	0.0182 (8)	0.0527 (9)	0.0121 (8)
S7	0.0380 (6)	0.1040 (11)	0.0764 (9)	0.0151 (7)	0.0151 (6)	0.0177 (8)
S8	0.0433 (6)	0.0743 (8)	0.0522 (7)	0.0097 (6)	0.0136 (5)	0.0046 (6)
Cl1	0.0906 (10)	0.1284 (14)	0.0643 (8)	−0.0295 (9)	0.0219 (7)	0.0091 (9)
Cl2	0.1194 (12)	0.1083 (13)	0.0734 (10)	0.0060 (10)	0.0381 (9)	−0.0087 (9)
Cl3	0.1054 (11)	0.1229 (13)	0.0670 (9)	−0.0287 (10)	0.0094 (8)	0.0124 (9)
Cl4	0.1069 (11)	0.1182 (13)	0.0750 (10)	−0.0046 (10)	0.0447 (8)	0.0084 (9)

Geometric parameters (Å, º)

C2—N3	1.306 (5)	C22—S6	1.756 (5)
C2—S1	1.725 (4)	C24—C25	1.360 (6)
C2—S2	1.750 (4)	C24—N23	1.381 (6)
C4—C5	1.364 (6)	C24—C26	1.468 (6)
C4—N3	1.388 (5)	C25—S5	1.705 (5)
C4—C6	1.466 (6)	C25—H25	0.9300
C5—S1	1.707 (5)	C26—C27	1.383 (6)
C5—H5	0.9300	C26—C31	1.391 (6)
C6—C11	1.375 (6)	C27—C28	1.376 (7)
C6—C7	1.398 (6)	C27—H27	0.9300
C7—C8	1.382 (6)	C28—C29	1.367 (7)
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.363 (7)	C29—C30	1.379 (7)
C8—H8	0.9300	C29—Cl3	1.733 (5)
C9—C10	1.376 (7)	C30—C31	1.377 (6)
C9—Cl1	1.739 (5)	C30—H30	0.9300
C10—C11	1.377 (6)	C31—H31	0.9300
C10—H10	0.9300	C32—N33	1.296 (5)
C11—H11	0.9300	C32—S7	1.722 (4)
C12—N13	1.298 (5)	C32—S8	1.761 (4)
C12—S4	1.731 (4)	C34—C35	1.355 (6)
C12—S3	1.759 (5)	C34—N33	1.383 (5)
C14—C15	1.359 (6)	C34—C36	1.471 (6)
C14—N13	1.379 (5)	C35—S7	1.702 (5)
C14—C16	1.474 (6)	C35—H35	0.9300
C15—S4	1.692 (5)	C36—C41	1.385 (6)
C15—H15	0.9300	C36—C37	1.390 (6)
C16—C17	1.391 (6)	C37—C38	1.375 (6)
C16—C21	1.393 (5)	C37—H37	0.9300
C17—C18	1.381 (6)	C38—C39	1.375 (7)
C17—H17	0.9300	C38—H38	0.9300
C18—C19	1.363 (7)	C39—C40	1.364 (6)
C18—H18	0.9300	C39—Cl4	1.745 (5)
C19—C20	1.370 (6)	C40—C41	1.386 (6)
C19—Cl2	1.749 (5)	C40—H40	0.9300
C20—C21	1.377 (6)	C41—H41	0.9300
C20—H20	0.9300	S2—S3	2.0281 (16)
C21—H21	0.9300	S6—S6^i	2.026 (2)
C22—N23	1.297 (5)	S8—S8^ii	2.031 (2)
C22—S5	1.725 (5)
N3—C2—S1	115.3 (3)	C24—C25—S5	111.6 (4)
N3—C2—S2	120.7 (3)	C24—C25—H25	124.2
S1—C2—S2	124.0 (2)	S5—C25—H25	124.2
C5—C4—N3	113.9 (4)	C27—C26—C31	117.9 (4)
C5—C4—C6	126.1 (4)	C27—C26—C24	122.0 (4)
N3—C4—C6	120.0 (4)	C31—C26—C24	120.1 (5)
C4—C5—S1	111.4 (4)	C28—C27—C26	120.9 (5)
C4—C5—H5	124.3	C28—C27—H27	119.5
S1—C5—H5	124.3	C26—C27—H27	119.5
C11—C6—C7	118.1 (4)	C29—C28—C27	120.2 (5)
C11—C6—C4	121.5 (4)	C29—C28—H28	119.9
C7—C6—C4	120.3 (4)	C27—C28—H28	119.9
C8—C7—C6	120.2 (4)	C28—C29—C30	120.3 (5)
C8—C7—H7	119.9	C28—C29—Cl3	120.2 (5)
C6—C7—H7	119.9	C30—C29—Cl3	119.5 (4)
C9—C8—C7	120.0 (5)	C31—C30—C29	119.2 (5)
C9—C8—H8	120.0	C31—C30—H30	120.4
C7—C8—H8	120.0	C29—C30—H30	120.4
C8—C9—C10	121.0 (4)	C30—C31—C26	121.4 (5)
C8—C9—Cl1	120.2 (4)	C30—C31—H31	119.3
C10—C9—Cl1	118.8 (4)	C26—C31—H31	119.3
C11—C10—C9	118.8 (5)	N33—C32—S7	116.2 (3)
C11—C10—H10	120.6	N33—C32—S8	120.6 (3)
C9—C10—H10	120.6	S7—C32—S8	122.8 (2)
C6—C11—C10	121.9 (5)	C35—C34—N33	113.6 (4)
C6—C11—H11	119.1	C35—C34—C36	126.9 (4)
C10—C11—H11	119.1	N33—C34—C36	119.5 (3)
N13—C12—S4	115.1 (3)	C34—C35—S7	112.3 (4)
N13—C12—S3	120.0 (3)	C34—C35—H35	123.9
S4—C12—S3	124.7 (2)	S7—C35—H35	123.9
C15—C14—N13	113.6 (4)	C41—C36—C37	118.6 (4)
C15—C14—C16	127.4 (4)	C41—C36—C34	120.5 (4)
N13—C14—C16	118.9 (4)	C37—C36—C34	121.0 (4)
C14—C15—S4	112.1 (3)	C38—C37—C36	121.2 (4)
C14—C15—H15	124.0	C38—C37—H37	119.4
S4—C15—H15	124.0	C36—C37—H37	119.4
C17—C16—C21	118.0 (4)	C37—C38—C39	118.9 (5)
C17—C16—C14	122.2 (4)	C37—C38—H38	120.6
C21—C16—C14	119.7 (4)	C39—C38—H38	120.6
C18—C17—C16	121.2 (4)	C40—C39—C38	121.5 (4)
C18—C17—H17	119.4	C40—C39—Cl4	118.9 (4)
C16—C17—H17	119.4	C38—C39—Cl4	119.5 (4)
C19—C18—C17	119.0 (5)	C39—C40—C41	119.5 (4)
C19—C18—H18	120.5	C39—C40—H40	120.3
C17—C18—H18	120.5	C41—C40—H40	120.3
C18—C19—C20	121.5 (5)	C36—C41—C40	120.4 (4)
C18—C19—Cl2	119.7 (4)	C36—C41—H41	119.8
C20—C19—Cl2	118.8 (4)	C40—C41—H41	119.8
C19—C20—C21	119.6 (4)	C2—N3—C4	110.6 (3)
C19—C20—H20	120.2	C12—N13—C14	110.8 (3)
C21—C20—H20	120.2	C22—N23—C24	110.8 (4)
C20—C21—C16	120.6 (4)	C32—N33—C34	110.2 (3)
C20—C21—H21	119.7	C5—S1—C2	88.8 (2)
C16—C21—H21	119.7	C2—S2—S3	101.91 (14)
N23—C22—S5	115.4 (4)	C12—S3—S2	102.89 (14)
N23—C22—S6	119.9 (4)	C15—S4—C12	88.3 (2)
S5—C22—S6	124.7 (3)	C25—S5—C22	88.4 (2)
C25—C24—N23	113.8 (4)	C22—S6—S6^i	102.81 (16)
C25—C24—C26	127.0 (5)	C35—S7—C32	87.8 (2)
N23—C24—C26	119.1 (4)	C32—S8—S8^ii	101.66 (14)
N3—C4—C5—S1	1.1 (5)	N33—C34—C36—C41	−18.4 (6)
C6—C4—C5—S1	−177.3 (3)	C35—C34—C36—C37	−16.2 (7)
C5—C4—C6—C11	−14.4 (7)	N33—C34—C36—C37	161.0 (4)
N3—C4—C6—C11	167.2 (4)	C41—C36—C37—C38	0.9 (7)
C5—C4—C6—C7	163.4 (4)	C34—C36—C37—C38	−178.5 (5)
N3—C4—C6—C7	−15.0 (6)	C36—C37—C38—C39	0.0 (8)
C11—C6—C7—C8	−2.3 (6)	C37—C38—C39—C40	−0.3 (8)
C4—C6—C7—C8	179.9 (4)	C37—C38—C39—Cl4	179.5 (4)
C6—C7—C8—C9	1.0 (7)	C38—C39—C40—C41	−0.3 (8)
C7—C8—C9—C10	0.6 (7)	Cl4—C39—C40—C41	179.9 (4)
C7—C8—C9—Cl1	−178.0 (3)	C37—C36—C41—C40	−1.5 (7)
C8—C9—C10—C11	−0.9 (8)	C34—C36—C41—C40	177.9 (4)
Cl1—C9—C10—C11	177.8 (4)	C39—C40—C41—C36	1.2 (7)
C7—C6—C11—C10	2.0 (7)	S1—C2—N3—C4	0.0 (4)
C4—C6—C11—C10	179.8 (4)	S2—C2—N3—C4	−178.9 (3)
C9—C10—C11—C6	−0.5 (8)	C5—C4—N3—C2	−0.7 (5)
N13—C14—C15—S4	0.5 (5)	C6—C4—N3—C2	177.9 (4)
C16—C14—C15—S4	−179.5 (4)	S4—C12—N13—C14	0.5 (5)
C15—C14—C16—C17	20.6 (7)	S3—C12—N13—C14	−174.3 (3)
N13—C14—C16—C17	−159.4 (4)	C15—C14—N13—C12	−0.6 (5)
C15—C14—C16—C21	−162.3 (5)	C16—C14—N13—C12	179.3 (4)
N13—C14—C16—C21	17.7 (6)	S5—C22—N23—C24	−0.1 (5)
C21—C16—C17—C18	−1.2 (7)	S6—C22—N23—C24	177.4 (3)
C14—C16—C17—C18	175.9 (4)	C25—C24—N23—C22	−0.1 (6)
C16—C17—C18—C19	−1.2 (8)	C26—C24—N23—C22	177.9 (4)
C17—C18—C19—C20	3.3 (8)	S7—C32—N33—C34	0.5 (5)
C17—C18—C19—Cl2	−176.9 (4)	S8—C32—N33—C34	173.3 (3)
C18—C19—C20—C21	−2.9 (8)	C35—C34—N33—C32	−0.7 (6)
Cl2—C19—C20—C21	177.2 (4)	C36—C34—N33—C32	−178.2 (4)
C19—C20—C21—C16	0.5 (7)	C4—C5—S1—C2	−0.9 (4)
C17—C16—C21—C20	1.5 (7)	N3—C2—S1—C5	0.6 (4)
C14—C16—C21—C20	−175.7 (4)	S2—C2—S1—C5	179.4 (3)
N23—C24—C25—S5	0.2 (5)	N3—C2—S2—S3	173.5 (3)
C26—C24—C25—S5	−177.6 (4)	S1—C2—S2—S3	−5.2 (3)
C25—C24—C26—C27	−22.0 (7)	N13—C12—S3—S2	−177.5 (3)
N23—C24—C26—C27	160.3 (4)	S4—C12—S3—S2	8.1 (3)
C25—C24—C26—C31	156.3 (5)	C2—S2—S3—C12	92.2 (2)
N23—C24—C26—C31	−21.4 (6)	C14—C15—S4—C12	−0.2 (4)
C31—C26—C27—C28	1.4 (7)	N13—C12—S4—C15	−0.2 (4)
C24—C26—C27—C28	179.8 (4)	S3—C12—S4—C15	174.4 (3)
C26—C27—C28—C29	−0.7 (7)	C24—C25—S5—C22	−0.2 (4)
C27—C28—C29—C30	0.2 (8)	N23—C22—S5—C25	0.2 (4)
C27—C28—C29—Cl3	178.9 (4)	S6—C22—S5—C25	−177.2 (3)
C28—C29—C30—C31	−0.4 (7)	N23—C22—S6—S6^i	177.0 (4)
Cl3—C29—C30—C31	−179.1 (4)	S5—C22—S6—S6^i	−5.8 (4)
C29—C30—C31—C26	1.2 (7)	C34—C35—S7—C32	−0.3 (4)
C27—C26—C31—C30	−1.7 (7)	N33—C32—S7—C35	−0.1 (4)
C24—C26—C31—C30	179.9 (4)	S8—C32—S7—C35	−172.7 (3)
N33—C34—C35—S7	0.6 (6)	N33—C32—S8—S8^ii	175.7 (3)
C36—C34—C35—S7	177.9 (4)	S7—C32—S8—S8^ii	−12.0 (3)
C35—C34—C36—C41	164.4 (5)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1, y, −z+3/2.