2,3,7,8-Tetra­kis(5-chloro­thien-2-yl)pyrazino[2,3-g]quinoxaline–para-xylene (3/2)

Bellizzi, M.; Crundwell, G.; Zeller, M.; Hunter, A.D.; McBurney, B.

doi:10.1107/S1600536806043248

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2,3,7,8-Tetrakis(5-chlorothien-2-yl)pyrazino[2,3-g]quinoxaline-para-xylene (3/2)

M. Bellizzi, G. Crundwell, M. Zeller, A. D. Hunter and B. McBurney

The asymmetric unit of the title compound, 3C₂₆H₁₀Cl₄N₄S₄·2C₈H₁₀, contains 1.5 quinoxaline molecules, one molecule having crystallographic inversion symmetry, and one para-xylene solvent molecule. The solvent molecules lie in channels along the [010] direction of the unit cell.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043248/fl2061sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043248/fl2061Isup2.hkl Contains datablock I

CCDC reference: 268585

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.039
wR factor = 0.105
Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.23
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit       P -1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT391_ALERT_3_C Deviating Methyl C47     H-C-H Bond Angle ......     101.00 Deg.
PLAT432_ALERT_2_C Short Inter X...Y Contact  Cl6    ..  C44     ..       3.23 Ang.

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      1.228
            Tmax scaled      0.826 Tmin scaled      0.722

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; 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: SHELXTL (Bruker, 1997).

2,3,7,8-Tetrakis(5-chlorothien-2-yl)pyrazino[2,3-g]quinoxaline– para-xylene (3/2) top

Crystal data top

3C₂₆H₁₀Cl₄N₄S₄·2C₈H₁₀	Z = 1
M_r = 2157.70	F(000) = 1094
Triclinic, P1	D_x = 1.596 Mg m⁻³
Hall symbol: P -1	Melting point: 373 K
a = 11.4457 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1201 (18) Å	Cell parameters from 21624 reflections
c = 17.054 (3) Å	θ = 2.4–30.5°
α = 80.079 (2)°	µ = 0.71 mm⁻¹
β = 75.752 (2)°	T = 100 K
γ = 81.631 (2)°	Block, red
V = 2245.5 (6) Å³	0.55 × 0.32 × 0.27 mm

Data collection top

Bruker SMART APEX diffractometer	13521 independent reflections
Radiation source: sealed tube	12535 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 30.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
T_min = 0.588, T_max = 0.673	k = −17→17
26805 measured reflections	l = −24→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0553P)² + 1.273P] where P = (F_o² + 2F_c²)/3
13521 reflections	(Δ/σ)_max = 0.001
686 parameters	Δρ_max = 1.20 e Å⁻³
0 restraints	Δρ_min = −0.80 e Å⁻³

Special details top

Experimental. All H were found in initial difference maps and refined isotropically. ¹H NMR (300 MHz, CDCl₃) δ 8.638 (s, 2H), 7.302 (d, 4H), 6.902 (d, 4H); ¹³C NMR (300 MHz, CDCl₃) δ 146.8, 140.2, 139.9, 135.7, 130.1, 127.7, 127.1.

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
N1	0.45455 (10)	−0.14299 (9)	0.27709 (7)	0.0134 (2)
C1	0.55096 (12)	−0.17750 (11)	0.30745 (8)	0.0131 (2)
C2	0.67058 (12)	−0.14714 (11)	0.26267 (8)	0.0135 (2)
N2	0.68295 (10)	−0.07016 (9)	0.19760 (7)	0.0131 (2)
C3	0.58199 (11)	−0.02803 (11)	0.16795 (8)	0.0123 (2)
C4	0.59334 (11)	0.05271 (11)	0.09841 (8)	0.0125 (2)
C5	0.49222 (11)	0.09248 (10)	0.06550 (8)	0.0117 (2)
N3	0.50424 (10)	0.17061 (9)	−0.00301 (7)	0.0126 (2)
C6	0.40770 (11)	0.20931 (11)	−0.03286 (8)	0.0118 (2)
C7	0.28968 (11)	0.17091 (11)	0.00806 (8)	0.0129 (2)
N4	0.27799 (10)	0.09189 (9)	0.07181 (7)	0.0134 (2)
C8	0.37836 (11)	0.05022 (11)	0.10255 (8)	0.0125 (2)
C9	0.36708 (11)	−0.03098 (11)	0.17171 (8)	0.0134 (2)
C10	0.46766 (12)	−0.06955 (11)	0.20547 (8)	0.0126 (2)
S1	0.39720 (3)	−0.31010 (3)	0.42079 (2)	0.01681 (7)
C11	0.52781 (12)	−0.24304 (11)	0.38947 (8)	0.0137 (2)
C12	0.58734 (13)	−0.25300 (13)	0.45163 (9)	0.0191 (3)
C13	0.52854 (13)	−0.31627 (13)	0.52514 (9)	0.0193 (3)
C14	0.42618 (13)	−0.35259 (12)	0.51615 (8)	0.0168 (2)
Cl1	0.32792 (3)	−0.43002 (3)	0.58965 (2)	0.02468 (8)
S2	0.90893 (3)	−0.12556 (3)	0.25637 (2)	0.01856 (7)
C15	0.78440 (12)	−0.20095 (11)	0.28399 (8)	0.0142 (2)
C16	0.81521 (13)	−0.30993 (12)	0.31638 (9)	0.0198 (3)
C17	0.93859 (13)	−0.33323 (12)	0.32081 (9)	0.0198 (3)
C18	0.99884 (12)	−0.24060 (12)	0.29167 (8)	0.0173 (2)
Cl2	1.14731 (3)	−0.23035 (3)	0.28872 (2)	0.02337 (8)
S3	0.58126 (3)	0.32556 (3)	−0.136966 (19)	0.01312 (7)
C19	0.43338 (11)	0.29006 (11)	−0.10797 (8)	0.0122 (2)
C20	0.36543 (12)	0.34620 (11)	−0.16195 (8)	0.0144 (2)
C21	0.43125 (13)	0.42064 (12)	−0.22548 (8)	0.0165 (2)
C22	0.54769 (12)	0.41788 (11)	−0.21862 (8)	0.0151 (2)
Cl3	0.65639 (3)	0.49634 (3)	−0.28131 (2)	0.02065 (7)
S4	0.08414 (3)	0.11952 (3)	−0.02758 (2)	0.01701 (7)
C23	0.17637 (12)	0.21509 (11)	−0.01843 (8)	0.0138 (2)
C24	0.12213 (12)	0.32384 (12)	−0.02921 (9)	0.0176 (2)
C25	0.00537 (13)	0.33031 (13)	−0.04596 (9)	0.0201 (3)
C26	−0.02520 (12)	0.22657 (13)	−0.04749 (9)	0.0187 (3)
Cl4	−0.15767 (3)	0.19619 (4)	−0.06473 (2)	0.02695 (9)
N5	0.70443 (10)	0.42337 (10)	0.06188 (7)	0.0141 (2)
C27	0.69469 (12)	0.34390 (11)	0.12533 (8)	0.0141 (2)
C28	0.57862 (12)	0.30221 (11)	0.16607 (8)	0.0132 (2)
N6	0.48150 (10)	0.33666 (9)	0.13601 (7)	0.0135 (2)
C29	0.49109 (12)	0.41575 (11)	0.06811 (8)	0.0126 (2)
C30	0.38864 (12)	0.45416 (11)	0.03598 (8)	0.0135 (2)
C31	0.39689 (11)	0.53778 (11)	−0.03159 (8)	0.0127 (2)
S5	0.89183 (3)	0.39871 (4)	0.17099 (3)	0.02435 (8)
C32	0.80871 (12)	0.30248 (12)	0.15186 (8)	0.0169 (2)
C33	0.87003 (13)	0.19667 (14)	0.15472 (9)	0.0216 (3)
C34	0.98581 (14)	0.19173 (16)	0.17286 (10)	0.0268 (3)
C35	1.00792 (14)	0.29417 (17)	0.18355 (10)	0.0287 (4)
Cl5	1.13613 (4)	0.32627 (6)	0.20598 (3)	0.04727 (14)
S6	0.40885 (3)	0.18880 (3)	0.27795 (2)	0.01609 (7)
C36	0.55583 (12)	0.22492 (11)	0.24284 (8)	0.0145 (2)
C37	0.62806 (13)	0.17320 (14)	0.29532 (9)	0.0212 (3)
C38	0.56604 (14)	0.10240 (14)	0.36310 (9)	0.0234 (3)
C39	0.44800 (13)	0.10316 (12)	0.36086 (8)	0.0183 (3)
Cl6	0.34076 (4)	0.03127 (3)	0.43074 (2)	0.02496 (8)
C40	0.94049 (14)	0.40998 (14)	0.49701 (10)	0.0236 (3)
C41	0.87515 (14)	0.50810 (14)	0.52316 (9)	0.0227 (3)
C42	0.93313 (14)	0.59977 (14)	0.52677 (9)	0.0220 (3)
C43	0.86224 (17)	0.70704 (17)	0.55333 (13)	0.0320 (4)
C44	1.08929 (15)	−0.07988 (15)	0.46680 (10)	0.0266 (3)
C45	1.02487 (16)	−0.00511 (15)	0.41732 (10)	0.0268 (3)
C46	0.93469 (15)	0.07590 (15)	0.44950 (10)	0.0250 (3)
C47	0.86613 (19)	0.15709 (19)	0.39554 (12)	0.0357 (4)
H4	0.6710 (18)	0.0784 (17)	0.0733 (12)	0.022 (5)*
H9	0.2922 (19)	−0.0591 (18)	0.1968 (13)	0.024 (5)*
H12	0.653 (2)	−0.2225 (19)	0.4459 (13)	0.030 (5)*
H13	0.555 (2)	−0.325 (2)	0.5732 (15)	0.036 (6)*
H16	0.7590 (19)	−0.3633 (18)	0.3336 (13)	0.028 (5)*
H17	0.972 (2)	−0.4010 (19)	0.3427 (14)	0.031 (6)*
H20	0.2814 (19)	0.3360 (17)	−0.1583 (13)	0.023 (5)*
H21	0.3957 (19)	0.4681 (18)	−0.2668 (13)	0.027 (5)*
H24	0.1601 (18)	0.3865 (17)	−0.0251 (12)	0.021 (5)*
H25	−0.0458 (18)	0.3988 (17)	−0.0542 (12)	0.020 (5)*
H30	0.3104 (19)	0.4221 (17)	0.0616 (12)	0.022 (5)*
H33	0.837 (2)	0.1291 (19)	0.1456 (13)	0.028 (5)*
H34	1.043 (2)	0.1256 (19)	0.1762 (14)	0.031 (6)*
H37	0.710 (2)	0.183 (2)	0.2865 (14)	0.033 (6)*
H38	0.603 (2)	0.055 (2)	0.4036 (15)	0.036 (6)*
H40	0.897 (2)	0.349 (2)	0.4945 (14)	0.033 (6)*
H41	0.791 (2)	0.5112 (18)	0.5385 (13)	0.027 (5)*
H44	1.155 (2)	−0.135 (2)	0.4437 (14)	0.034 (6)*
H45	1.041 (2)	−0.003 (2)	0.3560 (15)	0.041 (6)*
H43A	0.885 (3)	0.728 (3)	0.592 (2)	0.064 (9)*
H43B	0.869 (3)	0.766 (3)	0.5073 (19)	0.058 (8)*
H43C	0.777 (3)	0.698 (2)	0.5714 (18)	0.056 (8)*
H47A	0.866 (3)	0.127 (2)	0.3455 (18)	0.058 (8)*
H47B	0.777 (3)	0.172 (2)	0.4228 (17)	0.053 (8)*
H47C	0.907 (3)	0.230 (3)	0.3706 (18)	0.057 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0137 (5)	0.0127 (5)	0.0125 (5)	−0.0016 (4)	−0.0028 (4)	0.0014 (4)
C1	0.0146 (6)	0.0121 (5)	0.0120 (5)	−0.0015 (4)	−0.0033 (4)	0.0006 (4)
C2	0.0128 (5)	0.0138 (5)	0.0133 (5)	−0.0005 (4)	−0.0038 (4)	0.0000 (4)
N2	0.0122 (5)	0.0132 (5)	0.0134 (5)	−0.0009 (4)	−0.0039 (4)	0.0009 (4)
C3	0.0124 (5)	0.0121 (5)	0.0121 (5)	−0.0008 (4)	−0.0034 (4)	−0.0002 (4)
C4	0.0108 (5)	0.0125 (5)	0.0133 (5)	−0.0014 (4)	−0.0031 (4)	0.0009 (4)
C5	0.0117 (5)	0.0117 (5)	0.0114 (5)	−0.0013 (4)	−0.0032 (4)	0.0000 (4)
N3	0.0124 (5)	0.0128 (5)	0.0121 (5)	−0.0017 (4)	−0.0033 (4)	0.0010 (4)
C6	0.0128 (5)	0.0115 (5)	0.0110 (5)	−0.0015 (4)	−0.0035 (4)	−0.0001 (4)
C7	0.0119 (5)	0.0129 (5)	0.0141 (5)	−0.0009 (4)	−0.0044 (4)	−0.0008 (4)
N4	0.0114 (5)	0.0140 (5)	0.0141 (5)	−0.0013 (4)	−0.0042 (4)	0.0016 (4)
C8	0.0126 (5)	0.0119 (5)	0.0128 (5)	−0.0015 (4)	−0.0039 (4)	0.0006 (4)
C9	0.0108 (5)	0.0135 (5)	0.0147 (5)	−0.0021 (4)	−0.0029 (4)	0.0018 (4)
C10	0.0137 (5)	0.0113 (5)	0.0122 (5)	−0.0011 (4)	−0.0033 (4)	0.0003 (4)
S1	0.01593 (15)	0.02155 (16)	0.01274 (14)	−0.00611 (12)	−0.00526 (11)	0.00450 (11)
C11	0.0124 (5)	0.0142 (5)	0.0133 (5)	−0.0015 (4)	−0.0030 (4)	0.0019 (4)
C12	0.0180 (6)	0.0256 (7)	0.0145 (6)	−0.0062 (5)	−0.0060 (5)	0.0012 (5)
C13	0.0206 (6)	0.0245 (7)	0.0128 (6)	−0.0034 (5)	−0.0069 (5)	0.0028 (5)
C14	0.0179 (6)	0.0178 (6)	0.0126 (5)	−0.0028 (5)	−0.0033 (4)	0.0041 (5)
Cl1	0.02342 (17)	0.03060 (18)	0.01734 (15)	−0.00989 (14)	−0.00523 (12)	0.01063 (13)
S2	0.01338 (15)	0.01654 (15)	0.02412 (17)	−0.00262 (12)	−0.00633 (12)	0.00542 (12)
C15	0.0125 (5)	0.0147 (6)	0.0148 (5)	−0.0022 (4)	−0.0043 (4)	0.0024 (4)
C16	0.0165 (6)	0.0167 (6)	0.0247 (7)	−0.0029 (5)	−0.0069 (5)	0.0051 (5)
C17	0.0159 (6)	0.0179 (6)	0.0227 (7)	0.0017 (5)	−0.0060 (5)	0.0044 (5)
C18	0.0119 (5)	0.0211 (6)	0.0171 (6)	0.0006 (5)	−0.0042 (4)	0.0019 (5)
Cl2	0.01281 (14)	0.02818 (18)	0.02712 (17)	−0.00122 (12)	−0.00597 (12)	0.00274 (14)
S3	0.01263 (14)	0.01280 (14)	0.01313 (14)	−0.00210 (11)	−0.00324 (10)	0.00138 (10)
C19	0.0118 (5)	0.0128 (5)	0.0116 (5)	−0.0019 (4)	−0.0028 (4)	0.0000 (4)
C20	0.0148 (6)	0.0162 (6)	0.0121 (5)	−0.0009 (4)	−0.0051 (4)	0.0003 (4)
C21	0.0193 (6)	0.0155 (6)	0.0136 (6)	0.0003 (5)	−0.0055 (5)	0.0019 (5)
C22	0.0182 (6)	0.0126 (5)	0.0127 (5)	−0.0025 (5)	−0.0019 (4)	0.0016 (4)
Cl3	0.02328 (16)	0.01737 (15)	0.01772 (15)	−0.00627 (12)	0.00048 (12)	0.00323 (11)
S4	0.01250 (14)	0.01889 (15)	0.02032 (16)	−0.00292 (12)	−0.00606 (11)	−0.00018 (12)
C23	0.0112 (5)	0.0164 (6)	0.0133 (5)	−0.0028 (4)	−0.0038 (4)	0.0020 (4)
C24	0.0136 (6)	0.0187 (6)	0.0186 (6)	−0.0011 (5)	−0.0041 (5)	0.0028 (5)
C25	0.0138 (6)	0.0227 (7)	0.0206 (6)	0.0018 (5)	−0.0050 (5)	0.0041 (5)
C26	0.0110 (5)	0.0270 (7)	0.0169 (6)	−0.0016 (5)	−0.0055 (5)	0.0028 (5)
Cl4	0.01368 (15)	0.0414 (2)	0.02670 (18)	−0.00579 (14)	−0.00944 (13)	0.00207 (15)
N5	0.0136 (5)	0.0147 (5)	0.0140 (5)	−0.0009 (4)	−0.0047 (4)	0.0002 (4)
C27	0.0129 (5)	0.0148 (6)	0.0144 (6)	0.0001 (4)	−0.0045 (4)	−0.0009 (4)
C28	0.0146 (6)	0.0121 (5)	0.0123 (5)	−0.0002 (4)	−0.0034 (4)	−0.0005 (4)
N6	0.0147 (5)	0.0127 (5)	0.0131 (5)	−0.0015 (4)	−0.0041 (4)	−0.0002 (4)
C29	0.0142 (5)	0.0119 (5)	0.0120 (5)	−0.0014 (4)	−0.0041 (4)	−0.0009 (4)
C30	0.0125 (5)	0.0139 (5)	0.0143 (5)	−0.0017 (4)	−0.0041 (4)	−0.0001 (4)
C31	0.0127 (5)	0.0126 (5)	0.0130 (5)	−0.0011 (4)	−0.0039 (4)	−0.0012 (4)
S5	0.01927 (17)	0.02848 (19)	0.02710 (19)	−0.00778 (14)	−0.01155 (14)	0.00460 (15)
C32	0.0130 (6)	0.0214 (6)	0.0150 (6)	−0.0022 (5)	−0.0044 (4)	0.0030 (5)
C33	0.0173 (6)	0.0249 (7)	0.0185 (6)	0.0042 (5)	−0.0042 (5)	0.0024 (5)
C34	0.0161 (6)	0.0382 (9)	0.0193 (7)	0.0063 (6)	−0.0041 (5)	0.0068 (6)
C35	0.0132 (6)	0.0475 (10)	0.0221 (7)	−0.0061 (6)	−0.0075 (5)	0.0112 (7)
Cl5	0.0211 (2)	0.0793 (4)	0.0421 (3)	−0.0177 (2)	−0.01808 (18)	0.0155 (2)
S6	0.01552 (15)	0.01575 (15)	0.01576 (15)	−0.00234 (11)	−0.00364 (11)	0.00185 (11)
C36	0.0144 (6)	0.0149 (6)	0.0134 (5)	−0.0020 (4)	−0.0036 (4)	0.0007 (4)
C37	0.0165 (6)	0.0290 (7)	0.0160 (6)	−0.0022 (5)	−0.0061 (5)	0.0057 (5)
C38	0.0232 (7)	0.0268 (7)	0.0168 (6)	−0.0003 (6)	−0.0062 (5)	0.0071 (5)
C39	0.0214 (6)	0.0158 (6)	0.0148 (6)	−0.0022 (5)	−0.0017 (5)	0.0023 (5)
Cl6	0.02660 (18)	0.02193 (17)	0.02095 (16)	−0.00561 (14)	0.00096 (13)	0.00493 (13)
C40	0.0202 (7)	0.0279 (8)	0.0232 (7)	−0.0057 (6)	−0.0060 (5)	−0.0011 (6)
C41	0.0158 (6)	0.0317 (8)	0.0199 (7)	−0.0046 (6)	−0.0032 (5)	−0.0009 (6)
C42	0.0192 (6)	0.0281 (7)	0.0187 (6)	−0.0017 (6)	−0.0058 (5)	−0.0016 (5)
C43	0.0239 (8)	0.0327 (9)	0.0411 (10)	0.0015 (7)	−0.0084 (7)	−0.0122 (8)
C44	0.0240 (7)	0.0305 (8)	0.0259 (8)	−0.0023 (6)	−0.0069 (6)	−0.0047 (6)
C45	0.0283 (8)	0.0328 (8)	0.0207 (7)	−0.0056 (6)	−0.0068 (6)	−0.0038 (6)
C46	0.0224 (7)	0.0299 (8)	0.0244 (7)	−0.0063 (6)	−0.0086 (6)	−0.0008 (6)
C47	0.0358 (10)	0.0429 (11)	0.0292 (9)	0.0046 (8)	−0.0155 (7)	−0.0027 (8)

Geometric parameters (Å, º) top

N1—C1	1.3164 (17)	C25—H25	0.95 (2)
N1—C10	1.3714 (16)	C26—Cl4	1.7146 (14)
C1—C2	1.4589 (18)	N5—C27	1.3129 (17)
C1—C11	1.4674 (17)	N5—C31ⁱ	1.3731 (16)
C2—N2	1.3139 (16)	C27—C28	1.4571 (18)
C2—C15	1.4693 (18)	C27—C32	1.4770 (18)
N2—C3	1.3707 (16)	C28—N6	1.3208 (17)
C3—C4	1.3937 (17)	C28—C36	1.4628 (18)
C3—C10	1.4295 (18)	N6—C29	1.3630 (16)
C4—C5	1.3968 (17)	C29—C30	1.4004 (18)
C4—H4	0.96 (2)	C29—C31ⁱ	1.4302 (18)
C5—N3	1.3631 (16)	C30—C31	1.3913 (18)
C5—C8	1.4274 (17)	C30—H30	1.00 (2)
N3—C6	1.3205 (16)	C31—N5ⁱ	1.3731 (16)
C6—C7	1.4613 (17)	C31—C29ⁱ	1.4302 (18)
C6—C19	1.4667 (17)	S5—C35	1.7243 (18)
C7—N4	1.3131 (16)	S5—C32	1.7258 (15)
C7—C23	1.4750 (18)	C32—C33	1.369 (2)
N4—C8	1.3734 (16)	C33—C34	1.424 (2)
C8—C9	1.3922 (17)	C33—H33	1.00 (2)
C9—C10	1.3972 (17)	C34—C35	1.353 (3)
C9—H9	0.94 (2)	C34—H34	0.96 (2)
S1—C14	1.7167 (14)	C35—Cl5	1.7160 (17)
S1—C11	1.7297 (14)	S6—C39	1.7170 (15)
C11—C12	1.3749 (19)	S6—C36	1.7345 (14)
C12—C13	1.420 (2)	C36—C37	1.3775 (19)
C12—H12	0.86 (2)	C37—C38	1.417 (2)
C13—C14	1.361 (2)	C37—H37	0.93 (2)
C13—H13	0.92 (2)	C38—C39	1.360 (2)
C14—Cl1	1.7102 (14)	C38—H38	0.96 (2)
S2—C18	1.7216 (14)	C39—Cl6	1.7086 (14)
S2—C15	1.7288 (14)	C40—C41	1.390 (2)
C15—C16	1.3722 (19)	C40—C42ⁱⁱ	1.396 (2)
C16—C17	1.417 (2)	C40—H40	0.96 (2)
C16—H16	0.94 (2)	C41—C42	1.392 (2)
C17—C18	1.359 (2)	C41—H41	0.93 (2)
C17—H17	0.92 (2)	C42—C40ⁱⁱ	1.396 (2)
C18—Cl2	1.7096 (14)	C42—C43	1.506 (2)
S3—C22	1.7147 (14)	C43—H43A	0.86 (3)
S3—C19	1.7381 (13)	C43—H43B	0.96 (3)
C19—C20	1.3777 (17)	C43—H43C	0.97 (3)
C20—C21	1.4194 (19)	C44—C45	1.388 (2)
C20—H20	0.97 (2)	C44—C46ⁱⁱⁱ	1.394 (2)
C21—C22	1.3614 (19)	C44—H44	0.99 (2)
C21—H21	0.96 (2)	C45—C46	1.394 (2)
C22—Cl3	1.7131 (14)	C45—H45	1.01 (2)
S4—C26	1.7175 (15)	C46—C44ⁱⁱⁱ	1.394 (2)
S4—C23	1.7262 (14)	C46—C47	1.500 (2)
C23—C24	1.3751 (19)	C47—H47A	0.98 (3)
C24—C25	1.4225 (19)	C47—H47B	1.01 (3)
C24—H24	0.95 (2)	C47—H47C	1.04 (3)
C25—C26	1.359 (2)

C1—N1—C10	118.11 (11)	C26—C25—C24	111.59 (13)
N1—C1—C2	121.10 (11)	C26—C25—H25	124.1 (12)
N1—C1—C11	115.35 (11)	C24—C25—H25	124.3 (12)
C2—C1—C11	123.49 (11)	C25—C26—Cl4	126.85 (11)
N2—C2—C1	120.90 (12)	C25—C26—S4	113.12 (11)
N2—C2—C15	115.27 (11)	Cl4—C26—S4	120.02 (9)
C1—C2—C15	123.79 (11)	C27—N5—C31ⁱ	118.11 (12)
C2—N2—C3	118.04 (11)	N5—C27—C28	121.47 (12)
N2—C3—C4	118.99 (11)	N5—C27—C32	114.99 (12)
N2—C3—C10	120.69 (11)	C28—C27—C32	123.53 (12)
C4—C3—C10	120.27 (12)	N6—C28—C27	120.71 (12)
C3—C4—C5	119.48 (12)	N6—C28—C36	113.97 (12)
C3—C4—H4	119.2 (12)	C27—C28—C36	125.28 (12)
C5—C4—H4	121.3 (12)	C28—N6—C29	118.49 (11)
N3—C5—C4	119.18 (11)	N6—C29—C30	119.23 (12)
N3—C5—C8	120.59 (11)	N6—C29—C31ⁱ	120.60 (12)
C4—C5—C8	120.22 (11)	C30—C29—C31ⁱ	120.14 (11)
C6—N3—C5	118.80 (11)	C31—C30—C29	119.44 (12)
N3—C6—C7	120.46 (11)	C31—C30—H30	120.4 (12)
N3—C6—C19	113.47 (11)	C29—C30—H30	120.2 (12)
C7—C6—C19	126.07 (11)	N5ⁱ—C31—C30	119.19 (12)
N4—C7—C6	121.26 (11)	N5ⁱ—C31—C29ⁱ	120.38 (12)
N4—C7—C23	114.96 (11)	C30—C31—C29ⁱ	120.42 (11)
C6—C7—C23	123.77 (11)	C35—S5—C32	90.68 (8)
C7—N4—C8	118.43 (11)	C33—C32—C27	129.16 (14)
N4—C8—C9	119.36 (11)	C33—C32—S5	111.49 (11)
N4—C8—C5	120.26 (11)	C27—C32—S5	118.83 (11)
C9—C8—C5	120.36 (11)	C32—C33—C34	113.23 (15)
C8—C9—C10	119.50 (12)	C32—C33—H33	123.6 (13)
C8—C9—H9	121.0 (13)	C34—C33—H33	123.2 (13)
C10—C9—H9	119.5 (13)	C35—C34—C33	111.23 (14)
N1—C10—C9	119.58 (11)	C35—C34—H34	123.3 (14)
N1—C10—C3	120.17 (11)	C33—C34—H34	125.4 (14)
C9—C10—C3	120.16 (11)	C34—C35—Cl5	126.69 (13)
C14—S1—C11	90.66 (7)	C34—C35—S5	113.36 (12)
C12—C11—C1	130.69 (12)	Cl5—C35—S5	119.94 (12)
C12—C11—S1	111.42 (10)	C39—S6—C36	90.77 (7)
C1—C11—S1	117.56 (10)	C37—C36—C28	133.12 (13)
C11—C12—C13	113.14 (13)	C37—C36—S6	111.11 (10)
C11—C12—H12	122.4 (15)	C28—C36—S6	115.77 (10)
C13—C12—H12	124.4 (15)	C36—C37—C38	113.19 (13)
C14—C13—C12	111.14 (12)	C36—C37—H37	123.4 (15)
C14—C13—H13	126.0 (15)	C38—C37—H37	123.4 (15)
C12—C13—H13	122.7 (15)	C39—C38—C37	111.45 (13)
C13—C14—Cl1	126.41 (11)	C39—C38—H38	123.3 (14)
C13—C14—S1	113.62 (10)	C37—C38—H38	125.1 (14)
Cl1—C14—S1	119.95 (8)	C38—C39—Cl6	126.97 (12)
C18—S2—C15	91.09 (7)	C38—C39—S6	113.46 (11)
C16—C15—C2	130.21 (12)	Cl6—C39—S6	119.56 (9)
C16—C15—S2	110.86 (10)	C41—C40—C42ⁱⁱ	120.98 (15)
C2—C15—S2	118.55 (10)	C41—C40—H40	118.8 (14)
C15—C16—C17	113.68 (13)	C42ⁱⁱ—C40—H40	120.2 (14)
C15—C16—H16	122.4 (13)	C40—C41—C42	121.33 (14)
C17—C16—H16	123.9 (13)	C40—C41—H41	118.3 (13)
C18—C17—C16	111.33 (13)	C42—C41—H41	120.4 (13)
C18—C17—H17	124.3 (14)	C41—C42—C40ⁱⁱ	117.69 (15)
C16—C17—H17	124.3 (14)	C41—C42—C43	121.35 (14)
C17—C18—Cl2	126.74 (11)	C40ⁱⁱ—C42—C43	120.94 (15)
C17—C18—S2	113.00 (10)	C42—C43—H43A	113 (2)
Cl2—C18—S2	120.25 (9)	C42—C43—H43B	109.8 (18)
C22—S3—C19	90.76 (6)	H43A—C43—H43B	110 (3)
C20—C19—C6	134.17 (12)	C42—C43—H43C	110.1 (17)
C20—C19—S3	111.16 (10)	H43A—C43—H43C	108 (3)
C6—C19—S3	114.66 (9)	H43B—C43—H43C	106 (2)
C19—C20—C21	113.01 (12)	C45—C44—C46ⁱⁱⁱ	120.66 (16)
C19—C20—H20	124.5 (12)	C45—C44—H44	121.3 (13)
C21—C20—H20	122.5 (12)	C46ⁱⁱⁱ—C44—H44	118.0 (13)
C22—C21—C20	111.53 (12)	C44—C45—C46	121.27 (15)
C22—C21—H21	125.3 (13)	C44—C45—H45	123.3 (14)
C20—C21—H21	123.1 (13)	C46—C45—H45	115.4 (14)
C21—C22—Cl3	126.59 (11)	C45—C46—C44ⁱⁱⁱ	118.07 (15)
C21—C22—S3	113.50 (10)	C45—C46—C47	120.99 (16)
Cl3—C22—S3	119.91 (8)	C44ⁱⁱⁱ—C46—C47	120.94 (16)
C26—S4—C23	91.01 (7)	C46—C47—H47A	111.8 (17)
C24—C23—C7	130.04 (12)	C46—C47—H47B	112.2 (16)
C24—C23—S4	111.44 (10)	H47A—C47—H47B	105 (2)
C7—C23—S4	118.08 (10)	C46—C47—H47C	113.7 (16)
C23—C24—C25	112.83 (13)	H47A—C47—H47C	100 (2)
C23—C24—H24	122.2 (12)	H47B—C47—H47C	113 (2)
C25—C24—H24	125.0 (12)

C10—N1—C1—C2	−5.62 (19)	C7—C6—C19—S3	175.68 (10)
C10—N1—C1—C11	171.83 (11)	C22—S3—C19—C20	1.80 (11)
N1—C1—C2—N2	11.2 (2)	C22—S3—C19—C6	−177.83 (10)
C11—C1—C2—N2	−166.02 (12)	C6—C19—C20—C21	177.72 (14)
N1—C1—C2—C15	−166.66 (13)	S3—C19—C20—C21	−1.82 (15)
C11—C1—C2—C15	16.1 (2)	C19—C20—C21—C22	0.81 (17)
C1—C2—N2—C3	−6.85 (19)	C20—C21—C22—Cl3	−178.72 (10)
C15—C2—N2—C3	171.19 (11)	C20—C21—C22—S3	0.60 (16)
C2—N2—C3—C4	−179.23 (12)	C19—S3—C22—C21	−1.38 (11)
C2—N2—C3—C10	−1.94 (18)	C19—S3—C22—Cl3	177.99 (9)
N2—C3—C4—C5	177.10 (12)	N4—C7—C23—C24	124.56 (15)
C10—C3—C4—C5	−0.20 (19)	C6—C7—C23—C24	−56.2 (2)
C3—C4—C5—N3	−179.35 (12)	N4—C7—C23—S4	−47.17 (15)
C3—C4—C5—C8	−0.38 (19)	C6—C7—C23—S4	132.05 (11)
C4—C5—N3—C6	−178.77 (12)	C26—S4—C23—C24	0.96 (11)
C8—C5—N3—C6	2.27 (18)	C26—S4—C23—C7	174.16 (11)
C5—N3—C6—C7	1.45 (18)	C7—C23—C24—C25	−172.84 (13)
C5—N3—C6—C19	−178.17 (11)	S4—C23—C24—C25	−0.68 (16)
N3—C6—C7—N4	−4.71 (19)	C23—C24—C25—C26	−0.09 (18)
C19—C6—C7—N4	174.85 (12)	C24—C25—C26—Cl4	179.52 (11)
N3—C6—C7—C23	176.12 (12)	C24—C25—C26—S4	0.83 (17)
C19—C6—C7—C23	−4.3 (2)	C23—S4—C26—C25	−1.03 (12)
C6—C7—N4—C8	3.79 (19)	C23—S4—C26—Cl4	−179.82 (9)
C23—C7—N4—C8	−176.97 (11)	C31ⁱ—N5—C27—C28	−3.67 (19)
C7—N4—C8—C9	177.93 (12)	C31ⁱ—N5—C27—C32	177.09 (12)
C7—N4—C8—C5	−0.04 (19)	N5—C27—C28—N6	5.7 (2)
N3—C5—C8—N4	−3.14 (19)	C32—C27—C28—N6	−175.09 (13)
C4—C5—C8—N4	177.90 (12)	N5—C27—C28—C36	−171.73 (13)
N3—C5—C8—C9	178.91 (12)	C32—C27—C28—C36	7.4 (2)
C4—C5—C8—C9	−0.05 (19)	C27—C28—N6—C29	−2.85 (19)
N4—C8—C9—C10	−176.91 (12)	C36—C28—N6—C29	174.89 (11)
C5—C8—C9—C10	1.06 (19)	C28—N6—C29—C30	−179.28 (12)
C1—N1—C10—C9	−179.80 (12)	C28—N6—C29—C31ⁱ	−1.52 (18)
C1—N1—C10—C3	−3.16 (18)	N6—C29—C30—C31	177.72 (12)
C8—C9—C10—N1	175.01 (12)	C31ⁱ—C29—C30—C31	0.0 (2)
C8—C9—C10—C3	−1.63 (19)	C29—C30—C31—N5ⁱ	−178.77 (12)
N2—C3—C10—N1	7.34 (19)	C29—C30—C31—C29ⁱ	0.0 (2)
C4—C3—C10—N1	−175.41 (12)	N5—C27—C32—C33	−117.91 (17)
N2—C3—C10—C9	−176.04 (12)	C28—C27—C32—C33	62.9 (2)
C4—C3—C10—C9	1.21 (19)	N5—C27—C32—S5	53.00 (16)
N1—C1—C11—C12	−149.88 (15)	C28—C27—C32—S5	−126.22 (12)
C2—C1—C11—C12	27.5 (2)	C35—S5—C32—C33	−0.53 (12)
N1—C1—C11—S1	22.92 (16)	C35—S5—C32—C27	−172.97 (12)
C2—C1—C11—S1	−159.70 (10)	C27—C32—C33—C34	171.68 (14)
C14—S1—C11—C12	−1.06 (12)	S5—C32—C33—C34	0.22 (17)
C14—S1—C11—C1	−175.20 (11)	C32—C33—C34—C35	0.32 (19)
C1—C11—C12—C13	173.85 (14)	C33—C34—C35—Cl5	−179.83 (12)
S1—C11—C12—C13	0.70 (17)	C33—C34—C35—S5	−0.73 (18)
C11—C12—C13—C14	0.18 (19)	C32—S5—C35—C34	0.73 (13)
C12—C13—C14—Cl1	−179.29 (11)	C32—S5—C35—Cl5	179.90 (11)
C12—C13—C14—S1	−1.01 (17)	N6—C28—C36—C37	−177.30 (15)
C11—S1—C14—C13	1.20 (12)	C27—C28—C36—C37	0.3 (2)
C11—S1—C14—Cl1	179.60 (9)	N6—C28—C36—S6	2.34 (16)
N2—C2—C15—C16	−144.49 (15)	C27—C28—C36—S6	179.96 (10)
C1—C2—C15—C16	33.5 (2)	C39—S6—C36—C37	−1.15 (12)
N2—C2—C15—S2	27.74 (16)	C39—S6—C36—C28	179.13 (11)
C1—C2—C15—S2	−154.28 (11)	C28—C36—C37—C38	−179.08 (15)
C18—S2—C15—C16	−1.70 (12)	S6—C36—C37—C38	1.27 (18)
C18—S2—C15—C2	−175.35 (11)	C36—C37—C38—C39	−0.7 (2)
C2—C15—C16—C17	173.90 (14)	C37—C38—C39—Cl6	−179.29 (12)
S2—C15—C16—C17	1.21 (17)	C37—C38—C39—S6	−0.21 (19)
C15—C16—C17—C18	0.2 (2)	C36—S6—C39—C38	0.78 (13)
C16—C17—C18—Cl2	177.83 (12)	C36—S6—C39—Cl6	179.94 (9)
C16—C17—C18—S2	−1.49 (17)	C42ⁱⁱ—C40—C41—C42	−0.2 (3)
C15—S2—C18—C17	1.85 (12)	C40—C41—C42—C40ⁱⁱ	0.2 (3)
C15—S2—C18—Cl2	−177.51 (9)	C40—C41—C42—C43	178.63 (16)
N3—C6—C19—C20	175.74 (14)	C46ⁱⁱⁱ—C44—C45—C46	0.0 (3)
C7—C6—C19—C20	−3.8 (2)	C44—C45—C46—C44ⁱⁱⁱ	0.0 (3)
N3—C6—C19—S3	−4.73 (15)	C44—C45—C46—C47	179.48 (17)

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

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