4,10-Bis(pyridin-2-ylmeth-yl)-1,7-dithia-4,10-diazo-niacyclo-dodecane bis(perchlorate).

The asymmetric unit of the title compound C(20)H(30)N(4)S(2) (+). 2ClO(4) (-) comprises one macrocyclic cation and two perchlorate anions. In the cation, one of the protonated H atoms bound to the amide N atom is involved in an intra-molecular N-H⋯N hydrogen bond. The O atoms in the two perchlorate anions are disordered over two sets of sites with occupancy ratios of 0.65 (3):0.35 (3) and 0.640 (15):0.360 (15).

Related literature

For tunable physicochemical and functional properties of macrocyclic ligands, see: Fabbrizzi et al. (1999 ▶). For applications of transition metal complexes with macrocyclic ligands, see: De Silva et al. (2003 ▶); Habata et al. (2006 ▶); Bilgin et al. (2009 ▶); Bernier et al. (2011 ▶). For similar structures, see: Peng et al. (2009 ▶); Wasitlewski & Mattes (1990 ▶); Funkemeier & Mattes (1993 ▶); Chak & McAuley (2006 ▶).

Experimental

Crystal data

C20H30N4S2 2+·2ClO4 −

M = 589.52

Triclinic,

a = 10.4491 (6) Å

b = 11.6146 (7) Å

c = 11.7795 (7) Å

α = 96.167 (1)°

β = 90.340 (1)°

γ = 113.830 (1)°

V = 1298.23 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.850, T max = 0.891

12276 measured reflections

6516 independent reflections

4865 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.04

6516 reflections

407 parameters

84 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032715/jj2097sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032715/jj2097Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032715/jj2097Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H30N4S22+·2(ClO4−)	Z = 2
Mr = 589.52	F(000) = 616
Triclinic, P1	Dx = 1.508 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4491 (6) Å	Cell parameters from 5215 reflections
b = 11.6146 (7) Å	θ = 2.4–27.9°
c = 11.7795 (7) Å	µ = 0.46 mm−1
α = 96.167 (1)°	T = 296 K
β = 90.340 (1)°	Block, colorless
γ = 113.830 (1)°	0.35 × 0.30 × 0.25 mm
V = 1298.23 (13) Å3

Bruker APEXII CCD diffractometer	6516 independent reflections
Radiation source: fine-focus sealed tube	4865 reflections with I > 2σ(I)
graphite	Rint = 0.018
Thin slice φ & ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→12
Tmin = 0.850, Tmax = 0.891	k = −15→15
12276 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.4486P] where P = (Fo2 + 2Fc2)/3
6516 reflections	(Δ/σ)max = 0.001
407 parameters	Δρmax = 0.37 e Å−3
84 restraints	Δρmin = −0.37 e Å−3

Experimental. Characterization of ligand: 4,10-bis(pyridin-2-ylmethyl)-1,7-dithia-4,10-diazacyclododecane: 1H NMR (CDCl3): 8.455 (d, J = 4.52, py—H), 7.604 (t, J = 15.08, py—H), 7.475 (d, J = 7.79, py—H), 7.097 (t, J = 12.18, py—H), 3.739 (s, py—CH2), 2.802 (t, J = 13.08, NCH2CH2), 2.729 (t, J = 13.02, NCH2CH2). 13C NMR (CDCl3): 159.26, 149.06, 136.50, 123.05, 122.12, 61.35, 52.54, 26.66.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.39671 (6)	0.14286 (5)	0.65754 (5)	0.05266 (15)
S2	0.48251 (5)	0.13448 (5)	1.00606 (5)	0.04540 (14)
N1	0.21785 (17)	−0.03948 (15)	0.83251 (14)	0.0387 (3)
N2	0.61643 (17)	0.35034 (16)	0.84963 (16)	0.0444 (4)
N3	0.34391 (19)	−0.16697 (17)	0.71127 (16)	0.0513 (4)
N4	0.7232 (2)	0.19581 (18)	0.74762 (17)	0.0541 (4)
C1	0.4072 (3)	−0.2237 (3)	0.6405 (2)	0.0610 (6)
H1	0.4842	−0.1727	0.6033	0.073*
C2	0.3645 (3)	−0.3522 (2)	0.6201 (2)	0.0595 (6)
H2	0.4120	−0.3872	0.5709	0.071*
C3	0.2501 (3)	−0.4286 (2)	0.6738 (2)	0.0600 (6)
H3	0.2181	−0.5164	0.6609	0.072*
C4	0.1835 (2)	−0.3728 (2)	0.7471 (2)	0.0519 (5)
H4	0.1064	−0.4221	0.7852	0.062*
C5	0.23386 (19)	−0.24212 (18)	0.76281 (16)	0.0398 (4)
C6	0.1675 (2)	−0.17756 (18)	0.84537 (18)	0.0438 (4)
H6A	0.0665	−0.2179	0.8320	0.053*
H6B	0.1898	−0.1870	0.9229	0.053*
C7	0.1455 (2)	−0.0218 (2)	0.7285 (2)	0.0515 (5)
H7A	0.1414	−0.0853	0.6663	0.062*
H7B	0.0499	−0.0362	0.7458	0.062*
C8	0.2161 (2)	0.1076 (2)	0.6893 (2)	0.0532 (5)
H8A	0.2133	0.1712	0.7485	0.064*
H8B	0.1655	0.1112	0.6214	0.064*
C9	0.1998 (2)	0.0353 (2)	0.93856 (18)	0.0469 (5)
H9A	0.1049	−0.0067	0.9622	0.056*
H9B	0.2121	0.1186	0.9207	0.056*
C10	0.3007 (2)	0.05079 (19)	1.03664 (17)	0.0460 (5)
H10A	0.2865	−0.0324	1.0561	0.055*
H10B	0.2800	0.0965	1.1027	0.055*
C11	0.4678 (3)	0.3147 (2)	0.6720 (2)	0.0606 (6)
H11A	0.5516	0.3453	0.6291	0.073*
H11B	0.4001	0.3403	0.6381	0.073*
C12	0.5040 (2)	0.3773 (2)	0.7943 (2)	0.0543 (5)
H12A	0.5350	0.4682	0.7953	0.065*
H12B	0.4207	0.3470	0.8378	0.065*
C13	0.5041 (2)	0.29796 (19)	1.03629 (19)	0.0521 (5)
H13A	0.4205	0.3061	1.0094	0.063*
H13B	0.5174	0.3235	1.1182	0.063*
C14	0.6293 (2)	0.3825 (2)	0.9775 (2)	0.0533 (5)
H14A	0.6412	0.4698	0.9958	0.064*
H14B	0.7125	0.3757	1.0069	0.064*
C15	0.7559 (2)	0.4119 (2)	0.7978 (2)	0.0571 (6)
H15A	0.8295	0.4504	0.8579	0.069*
H15B	0.7552	0.4780	0.7543	0.069*
C16	0.7840 (2)	0.3135 (2)	0.72044 (18)	0.0479 (5)
C17	0.7505 (3)	0.1055 (3)	0.6860 (2)	0.0642 (6)
H17	0.7076	0.0225	0.7034	0.077*
C18	0.8396 (3)	0.1311 (3)	0.5980 (2)	0.0791 (9)
H18	0.8592	0.0671	0.5581	0.095*
C19	0.8991 (3)	0.2522 (4)	0.5698 (2)	0.0868 (10)
H19	0.9586	0.2712	0.5096	0.104*
C20	0.8703 (3)	0.3455 (3)	0.6311 (2)	0.0677 (7)
H20	0.9082	0.4282	0.6126	0.081*
Cl1	0.07973 (5)	0.30206 (4)	0.92855 (4)	0.04391 (13)
O1	0.1496 (11)	0.2960 (8)	1.0304 (5)	0.0704 (15)	0.65 (3)
O2	−0.0140 (9)	0.1779 (8)	0.8848 (8)	0.0671 (19)	0.65 (3)
O3	0.0093 (11)	0.3821 (9)	0.9534 (8)	0.0776 (19)	0.65 (3)
O4	0.1840 (8)	0.3539 (7)	0.8490 (7)	0.077 (2)	0.65 (3)
O1A	0.1935 (18)	0.3149 (12)	1.003 (2)	0.082 (5)	0.35 (3)
O2A	−0.0087 (13)	0.1694 (11)	0.9035 (16)	0.057 (3)	0.35 (3)
O3A	0.0013 (17)	0.3660 (14)	0.9828 (18)	0.075 (4)	0.35 (3)
O4A	0.130 (3)	0.3533 (14)	0.8256 (12)	0.106 (5)	0.35 (3)
Cl2	0.77446 (5)	0.71112 (5)	0.63800 (4)	0.04936 (14)
O5	0.7051 (8)	0.7250 (11)	0.7361 (3)	0.143 (5)	0.640 (15)
O6	0.8883 (4)	0.6809 (5)	0.6678 (5)	0.074 (2)	0.640 (15)
O7	0.8261 (6)	0.8223 (5)	0.5868 (9)	0.136 (4)	0.640 (15)
O8	0.6782 (6)	0.6138 (6)	0.5611 (5)	0.111 (3)	0.640 (15)
O5A	0.7899 (12)	0.8133 (10)	0.7147 (11)	0.124 (5)	0.360 (15)
O6A	0.8869 (9)	0.6775 (10)	0.6571 (9)	0.086 (5)	0.360 (15)
O7A	0.7803 (15)	0.7432 (18)	0.5294 (7)	0.152 (8)	0.360 (15)
O8A	0.6522 (6)	0.6099 (9)	0.6511 (16)	0.146 (10)	0.360 (15)
H1A	0.304 (2)	−0.011 (2)	0.8194 (19)	0.047 (6)*
H1B	0.594 (2)	0.268 (2)	0.8319 (19)	0.054 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0584 (3)	0.0548 (3)	0.0439 (3)	0.0224 (3)	0.0024 (2)	0.0043 (2)
S2	0.0438 (3)	0.0413 (3)	0.0502 (3)	0.0173 (2)	−0.0050 (2)	0.0018 (2)
N1	0.0315 (8)	0.0370 (8)	0.0453 (9)	0.0132 (6)	−0.0011 (7)	−0.0012 (7)
N2	0.0392 (9)	0.0323 (8)	0.0586 (11)	0.0122 (7)	0.0048 (7)	0.0023 (7)
N3	0.0492 (10)	0.0452 (9)	0.0525 (10)	0.0128 (8)	0.0094 (8)	0.0020 (8)
N4	0.0549 (11)	0.0486 (10)	0.0573 (11)	0.0211 (9)	0.0074 (9)	−0.0002 (8)
C1	0.0543 (13)	0.0687 (15)	0.0564 (14)	0.0219 (12)	0.0157 (11)	0.0039 (12)
C2	0.0682 (15)	0.0702 (15)	0.0518 (13)	0.0427 (13)	0.0046 (11)	−0.0035 (11)
C3	0.0730 (16)	0.0469 (12)	0.0644 (15)	0.0312 (12)	0.0016 (12)	−0.0018 (11)
C4	0.0514 (12)	0.0419 (11)	0.0581 (13)	0.0150 (9)	0.0062 (10)	0.0043 (9)
C5	0.0371 (9)	0.0387 (9)	0.0408 (10)	0.0136 (8)	−0.0026 (8)	0.0004 (8)
C6	0.0413 (10)	0.0366 (9)	0.0485 (11)	0.0113 (8)	0.0059 (8)	0.0023 (8)
C7	0.0433 (11)	0.0504 (12)	0.0571 (13)	0.0170 (9)	−0.0137 (9)	0.0002 (10)
C8	0.0517 (12)	0.0557 (13)	0.0560 (13)	0.0262 (10)	−0.0088 (10)	0.0051 (10)
C9	0.0407 (10)	0.0459 (11)	0.0560 (12)	0.0220 (9)	0.0065 (9)	−0.0047 (9)
C10	0.0532 (12)	0.0428 (10)	0.0397 (10)	0.0182 (9)	0.0102 (9)	0.0003 (8)
C11	0.0657 (15)	0.0578 (13)	0.0571 (14)	0.0208 (11)	−0.0007 (11)	0.0194 (11)
C12	0.0530 (12)	0.0455 (11)	0.0679 (15)	0.0236 (10)	−0.0001 (11)	0.0076 (10)
C13	0.0576 (13)	0.0412 (11)	0.0509 (12)	0.0167 (9)	0.0003 (10)	−0.0085 (9)
C14	0.0490 (12)	0.0411 (11)	0.0590 (13)	0.0107 (9)	−0.0052 (10)	−0.0081 (9)
C15	0.0444 (11)	0.0405 (11)	0.0772 (16)	0.0078 (9)	0.0129 (11)	0.0068 (10)
C16	0.0371 (10)	0.0536 (12)	0.0489 (12)	0.0151 (9)	0.0006 (9)	0.0020 (9)
C17	0.0759 (17)	0.0615 (15)	0.0601 (15)	0.0366 (13)	−0.0060 (13)	−0.0072 (12)
C18	0.0822 (19)	0.105 (2)	0.0592 (16)	0.0554 (19)	−0.0064 (14)	−0.0240 (16)
C19	0.0719 (19)	0.119 (3)	0.0550 (16)	0.0290 (19)	0.0155 (14)	−0.0095 (17)
C20	0.0587 (15)	0.0762 (17)	0.0548 (14)	0.0143 (13)	0.0084 (11)	0.0054 (12)
Cl1	0.0434 (3)	0.0362 (2)	0.0537 (3)	0.01821 (19)	0.0054 (2)	0.00373 (19)
O1	0.068 (4)	0.084 (3)	0.060 (3)	0.034 (3)	−0.012 (2)	0.0022 (18)
O2	0.057 (3)	0.047 (3)	0.086 (3)	0.012 (2)	−0.016 (2)	−0.003 (2)
O3	0.088 (4)	0.071 (3)	0.101 (4)	0.060 (3)	0.009 (3)	0.005 (3)
O4	0.076 (3)	0.060 (2)	0.079 (3)	0.0132 (19)	0.033 (2)	0.003 (2)
O1A	0.050 (6)	0.044 (4)	0.148 (11)	0.021 (4)	−0.039 (6)	−0.013 (5)
O2A	0.040 (5)	0.033 (4)	0.098 (8)	0.013 (3)	0.009 (5)	0.007 (4)
O3A	0.097 (6)	0.057 (4)	0.091 (8)	0.049 (4)	0.029 (5)	0.014 (5)
O4A	0.151 (14)	0.085 (6)	0.086 (6)	0.043 (8)	0.051 (7)	0.051 (5)
Cl2	0.0486 (3)	0.0477 (3)	0.0509 (3)	0.0183 (2)	−0.0043 (2)	0.0072 (2)
O5	0.141 (7)	0.260 (13)	0.065 (2)	0.127 (9)	0.025 (3)	−0.008 (4)
O6	0.054 (3)	0.069 (4)	0.092 (4)	0.015 (3)	−0.022 (3)	0.026 (3)
O7	0.135 (4)	0.090 (4)	0.179 (9)	0.028 (3)	−0.035 (5)	0.073 (4)
O8	0.091 (4)	0.101 (5)	0.120 (5)	0.035 (3)	−0.048 (3)	−0.053 (4)
O5A	0.108 (7)	0.107 (7)	0.154 (10)	0.055 (6)	0.017 (7)	−0.047 (7)
O6A	0.070 (8)	0.124 (11)	0.099 (8)	0.070 (7)	0.039 (6)	0.035 (7)
O7A	0.176 (14)	0.24 (2)	0.073 (6)	0.104 (16)	−0.007 (6)	0.081 (8)
O8A	0.039 (3)	0.096 (8)	0.30 (3)	0.005 (4)	0.001 (7)	0.101 (13)

S1—C8	1.813 (2)	C11—C12	1.514 (3)
S1—C11	1.814 (2)	C11—H11A	0.9700
S2—C10	1.810 (2)	C11—H11B	0.9700
S2—C13	1.814 (2)	C12—H12A	0.9700
N1—C6	1.498 (2)	C12—H12B	0.9700
N1—C9	1.501 (3)	C13—C14	1.508 (3)
N1—C7	1.511 (3)	C13—H13A	0.9700
N1—H1A	0.85 (2)	C13—H13B	0.9700
N2—C12	1.495 (3)	C14—H14A	0.9700
N2—C14	1.504 (3)	C14—H14B	0.9700
N2—C15	1.507 (3)	C15—C16	1.508 (3)
N2—H1B	0.89 (2)	C15—H15A	0.9700
N3—C5	1.328 (3)	C15—H15B	0.9700
N3—C1	1.344 (3)	C16—C20	1.373 (3)
N4—C16	1.330 (3)	C17—C18	1.373 (4)
N4—C17	1.338 (3)	C17—H17	0.9300
C1—C2	1.367 (3)	C18—C19	1.368 (5)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.374 (4)	C19—C20	1.373 (4)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.378 (3)	C20—H20	0.9300
C3—H3	0.9300	Cl1—O3	1.410 (6)
C4—C5	1.381 (3)	Cl1—O2	1.413 (7)
C4—H4	0.9300	Cl1—O4A	1.418 (10)
C5—C6	1.503 (3)	Cl1—O1A	1.422 (10)
C6—H6A	0.9700	Cl1—O1	1.423 (6)
C6—H6B	0.9700	Cl1—O3A	1.424 (11)
C7—C8	1.508 (3)	Cl1—O4	1.425 (6)
C7—H7A	0.9700	Cl1—O2A	1.437 (11)
C7—H7B	0.9700	Cl2—O5A	1.365 (6)
C8—H8A	0.9700	Cl2—O7A	1.365 (6)
C8—H8B	0.9700	Cl2—O8A	1.366 (5)
C9—C10	1.505 (3)	Cl2—O7	1.389 (4)
C9—H9A	0.9700	Cl2—O5	1.396 (4)
C9—H9B	0.9700	Cl2—O8	1.400 (4)
C10—H10A	0.9700	Cl2—O6A	1.403 (7)
C10—H10B	0.9700	Cl2—O6	1.421 (4)
C8—S1—C11	100.22 (12)	H13A—C13—H13B	108.2
C10—S2—C13	101.11 (10)	N2—C14—C13	113.20 (17)
C6—N1—C9	111.86 (16)	N2—C14—H14A	108.9
C6—N1—C7	110.19 (15)	C13—C14—H14A	108.9
C9—N1—C7	111.66 (16)	N2—C14—H14B	108.9
C6—N1—H1A	108.5 (15)	C13—C14—H14B	108.9
C9—N1—H1A	108.7 (15)	H14A—C14—H14B	107.8
C7—N1—H1A	105.7 (15)	N2—C15—C16	109.51 (17)
C12—N2—C14	112.94 (17)	N2—C15—H15A	109.8
C12—N2—C15	112.52 (18)	C16—C15—H15A	109.8
C14—N2—C15	111.17 (17)	N2—C15—H15B	109.8
C12—N2—H1B	106.4 (15)	C16—C15—H15B	109.8
C14—N2—H1B	109.7 (15)	H15A—C15—H15B	108.2
C15—N2—H1B	103.5 (15)	N4—C16—C20	123.1 (2)
C5—N3—C1	116.90 (19)	N4—C16—C15	115.22 (19)
C16—N4—C17	118.0 (2)	C20—C16—C15	121.6 (2)
N3—C1—C2	123.6 (2)	N4—C17—C18	122.2 (3)
N3—C1—H1	118.2	N4—C17—H17	118.9
C2—C1—H1	118.2	C18—C17—H17	118.9
C1—C2—C3	118.7 (2)	C19—C18—C17	119.1 (3)
C1—C2—H2	120.6	C19—C18—H18	120.5
C3—C2—H2	120.6	C17—C18—H18	120.5
C2—C3—C4	118.8 (2)	C18—C19—C20	119.4 (3)
C2—C3—H3	120.6	C18—C19—H19	120.3
C4—C3—H3	120.6	C20—C19—H19	120.3
C3—C4—C5	118.6 (2)	C16—C20—C19	118.2 (3)
C3—C4—H4	120.7	C16—C20—H20	120.9
C5—C4—H4	120.7	C19—C20—H20	120.9
N3—C5—C4	123.37 (19)	O3—Cl1—O2	111.7 (3)
N3—C5—C6	116.43 (17)	O3—Cl1—O4A	93.2 (8)
C4—C5—C6	120.16 (18)	O2—Cl1—O4A	100.5 (9)
N1—C6—C5	111.39 (16)	O3—Cl1—O1A	119.0 (9)
N1—C6—H6A	109.4	O2—Cl1—O1A	117.5 (7)
C5—C6—H6A	109.4	O4A—Cl1—O1A	110.3 (5)
N1—C6—H6B	109.4	O3—Cl1—O1	109.2 (3)
C5—C6—H6B	109.4	O2—Cl1—O1	108.7 (3)
H6A—C6—H6B	108.0	O4A—Cl1—O1	132.2 (10)
C8—C7—N1	113.97 (16)	O2—Cl1—O3A	108.6 (10)
C8—C7—H7A	108.8	O4A—Cl1—O3A	109.5 (5)
N1—C7—H7A	108.8	O1A—Cl1—O3A	110.0 (5)
C8—C7—H7B	108.8	O1—Cl1—O3A	96.1 (9)
N1—C7—H7B	108.8	O3—Cl1—O4	109.7 (3)
H7A—C7—H7B	107.7	O2—Cl1—O4	110.1 (3)
C7—C8—S1	111.49 (15)	O1A—Cl1—O4	85.3 (9)
C7—C8—H8A	109.3	O1—Cl1—O4	107.4 (3)
S1—C8—H8A	109.3	O3A—Cl1—O4	124.4 (7)
C7—C8—H8B	109.3	O3—Cl1—O2A	115.5 (9)
S1—C8—H8B	109.3	O4A—Cl1—O2A	109.6 (5)
H8A—C8—H8B	108.0	O1A—Cl1—O2A	108.1 (5)
N1—C9—C10	113.65 (16)	O1—Cl1—O2A	98.1 (8)
N1—C9—H9A	108.8	O3A—Cl1—O2A	109.4 (5)
C10—C9—H9A	108.8	O4—Cl1—O2A	115.9 (8)
N1—C9—H9B	108.8	O5A—Cl2—O7A	109.7 (5)
C10—C9—H9B	108.8	O5A—Cl2—O8A	111.1 (5)
H9A—C9—H9B	107.7	O7A—Cl2—O8A	111.1 (5)
C9—C10—S2	113.47 (14)	O5A—Cl2—O7	69.0 (5)
C9—C10—H10A	108.9	O8A—Cl2—O7	141.3 (4)
S2—C10—H10A	108.9	O5A—Cl2—O5	47.2 (4)
C9—C10—H10B	108.9	O7A—Cl2—O5	136.7 (5)
S2—C10—H10B	108.9	O8A—Cl2—O5	65.0 (5)
H10A—C10—H10B	107.7	O7—Cl2—O5	110.9 (3)
C12—C11—S1	114.19 (15)	O5A—Cl2—O8	143.4 (4)
C12—C11—H11A	108.7	O7A—Cl2—O8	67.6 (6)
S1—C11—H11A	108.7	O8A—Cl2—O8	46.7 (6)
C12—C11—H11B	108.7	O7—Cl2—O8	109.0 (3)
S1—C11—H11B	108.7	O5—Cl2—O8	108.0 (3)
H11A—C11—H11B	107.6	O5A—Cl2—O6A	108.4 (5)
N2—C12—C11	111.90 (19)	O7A—Cl2—O6A	107.7 (4)
N2—C12—H12A	109.2	O8A—Cl2—O6A	108.7 (4)
C11—C12—H12A	109.2	O7—Cl2—O6A	107.5 (5)
N2—C12—H12B	109.2	O5—Cl2—O6A	114.3 (5)
C11—C12—H12B	109.2	O8—Cl2—O6A	106.9 (5)
H12A—C12—H12B	107.9	O5A—Cl2—O6	104.1 (5)
C14—C13—S2	109.68 (15)	O7A—Cl2—O6	112.2 (6)
C14—C13—H13A	109.7	O8A—Cl2—O6	108.6 (4)
S2—C13—H13A	109.7	O7—Cl2—O6	108.8 (3)
C14—C13—H13B	109.7	O5—Cl2—O6	109.5 (3)
S2—C13—H13B	109.7	O8—Cl2—O6	110.6 (3)
C5—N3—C1—C2	−0.3 (4)	C8—S1—C11—C12	80.8 (2)
N3—C1—C2—C3	0.5 (4)	C14—N2—C12—C11	−165.53 (18)
C1—C2—C3—C4	−0.7 (4)	C15—N2—C12—C11	67.6 (2)
C2—C3—C4—C5	0.6 (4)	S1—C11—C12—N2	62.8 (2)
C1—N3—C5—C4	0.2 (3)	C10—S2—C13—C14	−159.75 (16)
C1—N3—C5—C6	177.6 (2)	C12—N2—C14—C13	67.5 (2)
C3—C4—C5—N3	−0.4 (3)	C15—N2—C14—C13	−164.93 (18)
C3—C4—C5—C6	−177.7 (2)	S2—C13—C14—N2	60.1 (2)
C9—N1—C6—C5	−157.83 (16)	C12—N2—C15—C16	−103.4 (2)
C7—N1—C6—C5	77.3 (2)	C14—N2—C15—C16	128.8 (2)
N3—C5—C6—N1	13.8 (2)	C17—N4—C16—C20	1.5 (3)
C4—C5—C6—N1	−168.68 (18)	C17—N4—C16—C15	−176.4 (2)
C6—N1—C7—C8	−163.84 (18)	N2—C15—C16—N4	−27.6 (3)
C9—N1—C7—C8	71.2 (2)	N2—C15—C16—C20	154.5 (2)
N1—C7—C8—S1	57.5 (2)	C16—N4—C17—C18	0.9 (4)
C11—S1—C8—C7	−157.69 (17)	N4—C17—C18—C19	−2.1 (4)
C6—N1—C9—C10	72.1 (2)	C17—C18—C19—C20	1.0 (5)
C7—N1—C9—C10	−163.87 (17)	N4—C16—C20—C19	−2.5 (4)
N1—C9—C10—S2	61.1 (2)	C15—C16—C20—C19	175.2 (2)
C13—S2—C10—C9	83.22 (16)	C18—C19—C20—C16	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1B···N4	0.89 (2)	2.06 (2)	2.661 (3)	123.6 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1B⋯N4	0.89 (2)	2.06 (2)	2.661 (3)	123.6 (19)