2-{[2,2-Bis(diethyl-amino)-ethan-2-ylium-thio-yl]sulfan-yl}-1,1-bis-(diethyl-amino)-ethyl-ium bis-(perchlorate).

The title salt, C(20)H(42)N(4)S(2) (2+)·2ClO(4) (-), was obtained from the reaction of bis-(diethyl-amino)-carbeniumdithio-carboxyl-ate, (Et(2)N)(2)C(2)S(2), with Fe(ClO(4))(2)·6H(2)O in CH(2)Cl(2). The title compound, in which one of the S atoms of (Et(2)N)(2)C(2)S(2) is bound to a 1,1-bis-(diethyl-amino)-ethane moiety, has two carbenium C atoms, and the charge compensation is provided by two perchlorate anions. The N(2)C-CS(2) bond length is 1.512 (4) Å, corresponding to a C-C single bond, and the dihedral angle between N(2)C- and -CS(2) planes [72.0 (2)°] is smaller than that of (Et(2)N)(2)C(2)S(2) [82.0 (1)°]. The crystal structure features C-H⋯S hydrogen bonds.

Related literature

For general background to bis­(N,N-disubstituted amino)­carbeniumdithio­carboxyl­ates, see: Winberg & Coffman (1965 ▶); Nagasawa et al. (1995 ▶); Nakayama & Akiyama (1992 ▶); Nakayama et al. (1997 ▶, 2000 ▶); Nakayama (2000 ▶, 2002 ▶); Miller et al. (2000 ▶); Fujihara et al. (2002 ▶); Siemeling et al. (2012 ▶). For transition metal complexes, see: Miyashita et al. (1998 ▶); Banerjee et al. (2002 ▶); Fujihara et al. (2004 ▶); Sugaya et al. (2009 ▶). For the cationic dimer of bis­(N,N-disubstituted amino)­carbeniumdithio­carboxyl­ates, see: Otani et al. (1998 ▶); Banerjee & Zubieta (2004 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H42N4S2 2+·2ClO4 −

M = 601.62

Orthorhombic,

a = 8.4158 (7) Å

b = 16.1889 (13) Å

c = 21.7213 (18) Å

V = 2959.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 150 K

0.32 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.881, T max = 0.923

21803 measured reflections

7058 independent reflections

5641 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.140

S = 1.02

7058 reflections

333 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 3081 Friedel pairs

Flack parameter: 0.00 (7)

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035453/rk2371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035453/rk2371Isup2.hkl

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

C20H42N4S22+·2ClO4−	F(000) = 1280
Mr = 601.62	Dx = 1.350 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3791 reflections
a = 8.4158 (7) Å	θ = 2.3–25.2°
b = 16.1889 (13) Å	µ = 0.41 mm−1
c = 21.7213 (18) Å	T = 150 K
V = 2959.4 (4) Å3	Block, red
Z = 4	0.32 × 0.21 × 0.20 mm

Bruker SMART APEX CCD diffractometer	7058 independent reflections
Radiation source: fine-focus sealed tube	5641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 8.366 pixels mm-1	θmax = 27.9°, θmin = 1.6°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→21
Tmin = 0.881, Tmax = 0.923	l = −18→28
21803 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0814P)2P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.003
7058 reflections	Δρmax = 0.70 e Å−3
333 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 3081 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (7)

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)- 6.5375 (0.0177) x + 3.5865 (0.0590) y + 12.8042 (0.0841) z = 5.1962 (0.0328)* 0.0000 (0.0000) N1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) N2Rms deviation of fitted atoms = 0.00006.1258 (0.0105) x + 10.6803 (0.0361) y + 4.0595 (0.0680) z = 11.1638 (0.0232)Angle to previous plane (with approximate e.s.d.) = 71.99 (0.22)* 0.0000 (0.0000) S1 * 0.0000 (0.0000) C1 * 0.0000 (0.0000) S2Rms deviation of fitted atoms = 0.0000

	x	y	z	Uiso*/Ueq
C1	0.0803 (3)	0.92906 (17)	0.18456 (13)	0.0266 (6)
C2	0.1428 (3)	0.87247 (17)	0.23435 (13)	0.0275 (6)
C3	−0.0518 (4)	0.7694 (2)	0.20201 (15)	0.0402 (8)
H3A	−0.0328	0.7193	0.1769	0.048*
H3B	−0.0864	0.8142	0.1741	0.048*
C4	−0.1802 (6)	0.7523 (4)	0.2484 (2)	0.0905 (19)
H4A	−0.1428	0.7108	0.2779	0.136*
H4B	−0.2750	0.7315	0.2272	0.136*
H4C	−0.2066	0.8033	0.2703	0.136*
C5	0.1951 (5)	0.7249 (2)	0.25762 (18)	0.0510 (9)
H5A	0.1389	0.6720	0.2506	0.061*
H5B	0.2093	0.7319	0.3026	0.061*
C6	0.3555 (7)	0.7219 (3)	0.2270 (2)	0.0891 (19)
H6A	0.3418	0.7134	0.1826	0.134*
H6B	0.4176	0.6762	0.2443	0.134*
H6C	0.4116	0.7741	0.2341	0.134*
C7	0.2630 (4)	0.8720 (2)	0.33875 (14)	0.0381 (8)
H7A	0.3331	0.9100	0.3619	0.046*
H7B	0.3157	0.8174	0.3369	0.046*
C8	0.1063 (5)	0.8636 (2)	0.37214 (16)	0.0456 (8)
H8A	0.0482	0.9160	0.3698	0.068*
H8B	0.1260	0.8496	0.4154	0.068*
H8C	0.0432	0.8198	0.3529	0.068*
C9	0.3319 (4)	0.98111 (19)	0.26184 (16)	0.0378 (7)
H9A	0.3147	1.0217	0.2953	0.045*
H9B	0.2930	1.0058	0.2230	0.045*
C10	0.5082 (5)	0.9627 (3)	0.2561 (2)	0.0628 (11)
H10A	0.5488	0.9430	0.2958	0.094*
H10B	0.5649	1.0131	0.2442	0.094*
H10C	0.5247	0.9201	0.2248	0.094*
C11	0.1161 (3)	0.98670 (17)	0.06450 (13)	0.0274 (6)
H11A	0.1500	1.0391	0.0841	0.033*
H11B	0.1794	0.9803	0.0264	0.033*
C12	−0.0572 (3)	0.99655 (17)	0.04567 (12)	0.0258 (6)
C13	−0.3217 (4)	0.9369 (2)	0.04633 (17)	0.0427 (8)
H13A	−0.3786	0.9335	0.0065	0.051*
H13B	−0.3464	0.9911	0.0652	0.051*
C14	−0.3781 (5)	0.8689 (3)	0.0880 (2)	0.0585 (11)
H14A	−0.3607	0.8154	0.0680	0.088*
H14B	−0.4917	0.8761	0.0964	0.088*
H14C	−0.3187	0.8708	0.1268	0.088*
C15	−0.0855 (4)	0.85068 (19)	0.01460 (15)	0.0334 (7)
H15A	−0.1061	0.8083	0.0465	0.040*
H15B	0.0309	0.8551	0.0090	0.040*
C16	−0.1614 (5)	0.8243 (2)	−0.04533 (17)	0.0479 (9)
H16A	−0.2754	0.8154	−0.0390	0.072*
H16B	−0.1123	0.7728	−0.0595	0.072*
H16C	−0.1457	0.8675	−0.0763	0.072*
C17	−0.2247 (5)	1.0945 (3)	−0.01183 (18)	0.0527 (10)
H17A	−0.2348	1.1554	−0.0140	0.063*
H17B	−0.3297	1.0719	−0.0001	0.063*
C18	−0.1813 (5)	1.0624 (3)	−0.07407 (18)	0.0593 (11)
H18A	−0.0680	1.0720	−0.0816	0.089*
H18B	−0.2440	1.0912	−0.1055	0.089*
H18C	−0.2035	1.0031	−0.0760	0.089*
C19	−0.0413 (5)	1.1461 (2)	0.06844 (18)	0.0482 (9)
H19A	0.0134	1.1278	0.1064	0.058*
H19B	−0.1296	1.1830	0.0807	0.058*
C20	0.0738 (6)	1.1938 (2)	0.0293 (2)	0.0675 (13)
H20A	0.1609	1.1574	0.0166	0.101*
H20B	0.1165	1.2402	0.0530	0.101*
H20C	0.0188	1.2148	−0.0073	0.101*
N1	0.0976 (3)	0.79387 (15)	0.23329 (12)	0.0338 (6)
N2	0.2405 (3)	0.90405 (16)	0.27537 (11)	0.0304 (5)
N3	−0.1489 (3)	0.93085 (14)	0.03540 (12)	0.0282 (5)
N4	−0.1076 (3)	1.07317 (15)	0.03665 (13)	0.0372 (7)
O1	0.6764 (4)	0.61374 (17)	0.34864 (12)	0.0564 (7)
O2	0.4000 (4)	0.6153 (3)	0.35918 (17)	0.0945 (12)
O3	0.5508 (5)	0.73360 (19)	0.37979 (16)	0.0918 (12)
O4	0.5645 (4)	0.6189 (2)	0.44602 (13)	0.0710 (9)
O5	0.6992 (4)	0.53757 (17)	0.07763 (13)	0.0663 (9)
O6	0.9442 (4)	0.58632 (19)	0.11349 (17)	0.0749 (9)
O7	0.7235 (4)	0.6719 (2)	0.11376 (18)	0.0878 (11)
O8	0.8378 (4)	0.6359 (2)	0.02204 (14)	0.0705 (9)
Cl1	0.54701 (11)	0.64601 (6)	0.38326 (4)	0.0490 (2)
Cl2	0.80215 (10)	0.60677 (5)	0.08213 (4)	0.0389 (2)
S1	0.16983 (8)	0.90400 (4)	0.11539 (3)	0.02782 (16)
S2	−0.05125 (11)	0.99911 (6)	0.19878 (4)	0.0407 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0269 (15)	0.0247 (14)	0.0283 (14)	−0.0014 (11)	−0.0026 (12)	−0.0001 (12)
C2	0.0311 (15)	0.0273 (14)	0.0242 (14)	0.0008 (12)	−0.0004 (12)	0.0014 (12)
C3	0.0454 (19)	0.0397 (17)	0.0354 (17)	−0.0164 (16)	−0.0078 (15)	0.0043 (15)
C4	0.072 (3)	0.147 (5)	0.053 (3)	−0.055 (4)	0.005 (3)	0.008 (3)
C5	0.078 (3)	0.0277 (16)	0.047 (2)	0.0047 (18)	−0.012 (2)	0.0011 (15)
C6	0.121 (5)	0.085 (3)	0.061 (3)	0.061 (3)	0.021 (3)	0.016 (3)
C7	0.0467 (19)	0.0410 (18)	0.0266 (15)	0.0019 (15)	−0.0076 (14)	0.0004 (14)
C8	0.060 (2)	0.0443 (19)	0.0328 (18)	−0.0042 (17)	0.0051 (16)	0.0030 (16)
C9	0.0430 (18)	0.0341 (16)	0.0362 (17)	−0.0109 (15)	−0.0032 (15)	−0.0036 (14)
C10	0.046 (2)	0.083 (3)	0.059 (3)	−0.014 (2)	0.0002 (19)	0.000 (2)
C11	0.0263 (14)	0.0280 (14)	0.0279 (15)	−0.0055 (11)	0.0043 (11)	0.0046 (12)
C12	0.0285 (14)	0.0261 (13)	0.0228 (13)	0.0040 (12)	0.0070 (12)	0.0036 (12)
C13	0.0271 (16)	0.052 (2)	0.049 (2)	0.0059 (15)	−0.0021 (15)	−0.0039 (17)
C14	0.0356 (19)	0.075 (3)	0.065 (3)	−0.0094 (19)	0.0131 (19)	0.005 (2)
C15	0.0310 (16)	0.0314 (16)	0.0377 (16)	−0.0018 (13)	−0.0020 (13)	−0.0010 (13)
C16	0.050 (2)	0.048 (2)	0.046 (2)	0.0013 (18)	−0.0098 (18)	−0.0121 (17)
C17	0.048 (2)	0.052 (2)	0.058 (2)	0.0180 (19)	0.0010 (18)	0.0167 (19)
C18	0.047 (2)	0.083 (3)	0.047 (2)	0.017 (2)	−0.0052 (19)	0.021 (2)
C19	0.065 (2)	0.0273 (16)	0.052 (2)	0.0037 (17)	0.012 (2)	−0.0016 (16)
C20	0.097 (4)	0.036 (2)	0.069 (3)	−0.011 (2)	0.008 (3)	0.0147 (19)
N1	0.0466 (16)	0.0240 (12)	0.0306 (14)	−0.0041 (11)	−0.0069 (12)	0.0060 (11)
N2	0.0334 (13)	0.0315 (13)	0.0263 (12)	0.0000 (11)	−0.0033 (10)	0.0040 (11)
N3	0.0217 (12)	0.0288 (12)	0.0342 (13)	0.0015 (10)	−0.0012 (10)	0.0016 (11)
N4	0.0410 (15)	0.0299 (13)	0.0407 (16)	0.0100 (12)	0.0044 (13)	0.0078 (12)
O1	0.0625 (17)	0.0525 (15)	0.0543 (16)	0.0216 (14)	0.0191 (14)	0.0003 (13)
O2	0.0563 (19)	0.143 (3)	0.084 (2)	0.002 (2)	−0.0089 (17)	0.042 (2)
O3	0.143 (3)	0.0545 (17)	0.078 (2)	0.049 (2)	0.012 (3)	0.0031 (17)
O4	0.0634 (19)	0.102 (2)	0.0473 (16)	0.0145 (18)	0.0108 (14)	0.0237 (17)
O5	0.093 (2)	0.0591 (16)	0.0472 (15)	−0.0381 (17)	−0.0234 (16)	0.0195 (13)
O6	0.0643 (19)	0.0660 (17)	0.094 (2)	0.0070 (16)	−0.0421 (19)	0.0015 (18)
O7	0.066 (2)	0.096 (2)	0.102 (3)	0.0200 (18)	−0.016 (2)	−0.057 (2)
O8	0.071 (2)	0.086 (2)	0.0544 (16)	−0.0347 (18)	−0.0061 (15)	0.0210 (16)
Cl1	0.0517 (5)	0.0519 (5)	0.0434 (5)	0.0224 (4)	0.0125 (4)	0.0125 (4)
Cl2	0.0420 (4)	0.0345 (4)	0.0402 (4)	−0.0056 (3)	−0.0080 (3)	0.0004 (3)
S1	0.0269 (3)	0.0302 (3)	0.0263 (3)	0.0038 (3)	−0.0007 (3)	0.0006 (3)
S2	0.0430 (5)	0.0411 (4)	0.0380 (4)	0.0119 (4)	0.0069 (4)	0.0016 (4)

C1—C2	1.512 (4)	C12—N3	1.333 (4)
C1—S2	1.615 (3)	C13—N3	1.476 (4)
C1—S1	1.729 (3)	C13—C14	1.503 (5)
C2—N2	1.316 (4)	C13—H13A	0.9900
C2—N1	1.328 (4)	C13—H13B	0.9900
C3—N1	1.483 (4)	C14—H14A	0.9800
C3—C4	1.504 (6)	C14—H14B	0.9800
C3—H3A	0.9900	C14—H14C	0.9800
C3—H3B	0.9900	C15—N3	1.474 (4)
C4—H4A	0.9800	C15—C16	1.512 (5)
C4—H4B	0.9800	C15—H15A	0.9900
C4—H4C	0.9800	C15—H15B	0.9900
C5—N1	1.483 (4)	C16—H16A	0.9800
C5—C6	1.506 (7)	C16—H16B	0.9800
C5—H5A	0.9900	C16—H16C	0.9800
C5—H5B	0.9900	C17—N4	1.483 (5)
C6—H6A	0.9800	C17—C18	1.494 (5)
C6—H6B	0.9800	C17—H17A	0.9900
C6—H6C	0.9800	C17—H17B	0.9900
C7—N2	1.483 (4)	C18—H18A	0.9800
C7—C8	1.511 (5)	C18—H18B	0.9800
C7—H7A	0.9900	C18—H18C	0.9800
C7—H7B	0.9900	C19—N4	1.477 (4)
C8—H8A	0.9800	C19—C20	1.503 (5)
C8—H8B	0.9800	C19—H19A	0.9900
C8—H8C	0.9800	C19—H19B	0.9900
C9—N2	1.495 (4)	C20—H20A	0.9800
C9—C10	1.518 (5)	C20—H20B	0.9800
C9—H9A	0.9900	C20—H20C	0.9800
C9—H9B	0.9900	Cl1—O3	1.420 (3)
C10—H10A	0.9800	Cl1—O1	1.423 (3)
C10—H10B	0.9800	Cl1—O2	1.432 (4)
C10—H10C	0.9800	Cl1—O4	1.439 (3)
C11—C12	1.523 (4)	Cl2—O6	1.415 (3)
C11—S1	1.794 (3)	Cl2—O5	1.420 (3)
C11—H11A	0.9900	Cl2—O8	1.420 (3)
C11—H11B	0.9900	Cl2—O7	1.422 (3)
C12—N4	1.326 (4)
C2—C1—S2	121.8 (2)	H13A—C13—H13B	108.0
C2—C1—S1	109.1 (2)	C13—C14—H14A	109.5
S2—C1—S1	129.03 (18)	C13—C14—H14B	109.5
N2—C2—N1	124.3 (3)	H14A—C14—H14B	109.5
N2—C2—C1	117.8 (2)	C13—C14—H14C	109.5
N1—C2—C1	117.9 (3)	H14A—C14—H14C	109.5
N1—C3—C4	110.6 (3)	H14B—C14—H14C	109.5
N1—C3—H3A	109.5	N3—C15—C16	111.1 (3)
C4—C3—H3A	109.5	N3—C15—H15A	109.4
N1—C3—H3B	109.5	C16—C15—H15A	109.4
C4—C3—H3B	109.5	N3—C15—H15B	109.4
H3A—C3—H3B	108.1	C16—C15—H15B	109.4
C3—C4—H4A	109.5	H15A—C15—H15B	108.0
C3—C4—H4B	109.5	C15—C16—H16A	109.5
H4A—C4—H4B	109.5	C15—C16—H16B	109.5
C3—C4—H4C	109.5	H16A—C16—H16B	109.5
H4A—C4—H4C	109.5	C15—C16—H16C	109.5
H4B—C4—H4C	109.5	H16A—C16—H16C	109.5
N1—C5—C6	111.3 (3)	H16B—C16—H16C	109.5
N1—C5—H5A	109.4	N4—C17—C18	113.5 (3)
C6—C5—H5A	109.4	N4—C17—H17A	108.9
N1—C5—H5B	109.4	C18—C17—H17A	108.9
C6—C5—H5B	109.4	N4—C17—H17B	108.9
H5A—C5—H5B	108.0	C18—C17—H17B	108.9
C5—C6—H6A	109.5	H17A—C17—H17B	107.7
C5—C6—H6B	109.5	C17—C18—H18A	109.5
H6A—C6—H6B	109.5	C17—C18—H18B	109.5
C5—C6—H6C	109.5	H18A—C18—H18B	109.5
H6A—C6—H6C	109.5	C17—C18—H18C	109.5
H6B—C6—H6C	109.5	H18A—C18—H18C	109.5
N2—C7—C8	111.4 (3)	H18B—C18—H18C	109.5
N2—C7—H7A	109.3	N4—C19—C20	112.9 (3)
C8—C7—H7A	109.3	N4—C19—H19A	109.0
N2—C7—H7B	109.3	C20—C19—H19A	109.0
C8—C7—H7B	109.3	N4—C19—H19B	109.0
H7A—C7—H7B	108.0	C20—C19—H19B	109.0
C7—C8—H8A	109.5	H19A—C19—H19B	107.8
C7—C8—H8B	109.5	C19—C20—H20A	109.5
H8A—C8—H8B	109.5	C19—C20—H20B	109.5
C7—C8—H8C	109.5	H20A—C20—H20B	109.5
H8A—C8—H8C	109.5	C19—C20—H20C	109.5
H8B—C8—H8C	109.5	H20A—C20—H20C	109.5
N2—C9—C10	110.8 (3)	H20B—C20—H20C	109.5
N2—C9—H9A	109.5	O3—Cl1—O1	108.8 (2)
C10—C9—H9A	109.5	O3—Cl1—O2	110.2 (3)
N2—C9—H9B	109.5	O1—Cl1—O2	109.9 (2)
C10—C9—H9B	109.5	O3—Cl1—O4	110.6 (2)
H9A—C9—H9B	108.1	O1—Cl1—O4	108.10 (18)
C9—C10—H10A	109.5	O2—Cl1—O4	109.2 (2)
C9—C10—H10B	109.5	O6—Cl2—O5	111.35 (18)
H10A—C10—H10B	109.5	O6—Cl2—O8	110.0 (2)
C9—C10—H10C	109.5	O5—Cl2—O8	109.14 (17)
H10A—C10—H10C	109.5	O6—Cl2—O7	109.5 (2)
H10B—C10—H10C	109.5	O5—Cl2—O7	109.5 (2)
C12—C11—S1	119.01 (19)	O8—Cl2—O7	107.2 (2)
C12—C11—H11A	107.6	C2—N1—C5	123.8 (3)
S1—C11—H11A	107.6	C2—N1—C3	120.5 (3)
C12—C11—H11B	107.6	C5—N1—C3	115.5 (3)
S1—C11—H11B	107.6	C2—N2—C7	124.9 (3)
H11A—C11—H11B	107.0	C2—N2—C9	120.8 (3)
N4—C12—N3	122.4 (3)	C7—N2—C9	114.1 (3)
N4—C12—C11	116.4 (3)	C12—N3—C15	122.9 (2)
N3—C12—C11	121.1 (2)	C12—N3—C13	119.4 (3)
N3—C13—C14	111.1 (3)	C15—N3—C13	117.7 (2)
N3—C13—H13A	109.4	C12—N4—C19	123.9 (3)
C14—C13—H13A	109.4	C12—N4—C17	122.4 (3)
N3—C13—H13B	109.4	C19—N4—C17	113.4 (3)
C14—C13—H13B	109.4	C1—S1—C11	104.50 (14)
S2—C1—C2—N2	−73.0 (3)	C10—C9—N2—C7	72.0 (4)
S1—C1—C2—N2	107.7 (3)	N4—C12—N3—C15	148.3 (3)
S2—C1—C2—N1	108.1 (3)	C11—C12—N3—C15	−27.5 (4)
S1—C1—C2—N1	−71.2 (3)	N4—C12—N3—C13	−33.0 (4)
S1—C11—C12—N4	146.7 (2)	C11—C12—N3—C13	151.1 (3)
S1—C11—C12—N3	−37.2 (4)	C16—C15—N3—C12	−122.3 (3)
N2—C2—N1—C5	−27.7 (5)	C16—C15—N3—C13	59.0 (4)
C1—C2—N1—C5	151.2 (3)	C14—C13—N3—C12	−127.1 (3)
N2—C2—N1—C3	157.5 (3)	C14—C13—N3—C15	51.6 (4)
C1—C2—N1—C3	−23.6 (4)	N3—C12—N4—C19	155.1 (3)
C6—C5—N1—C2	−57.2 (5)	C11—C12—N4—C19	−28.8 (4)
C6—C5—N1—C3	117.8 (4)	N3—C12—N4—C17	−31.9 (4)
C4—C3—N1—C2	−103.8 (4)	C11—C12—N4—C17	144.2 (3)
C4—C3—N1—C5	81.1 (5)	C20—C19—N4—C12	100.6 (4)
N1—C2—N2—C7	−26.8 (5)	C20—C19—N4—C17	−72.9 (4)
C1—C2—N2—C7	154.3 (3)	C18—C17—N4—C12	−51.3 (5)
N1—C2—N2—C9	157.3 (3)	C18—C17—N4—C19	122.4 (4)
C1—C2—N2—C9	−21.6 (4)	C2—C1—S1—C11	−169.24 (19)
C8—C7—N2—C2	−52.6 (4)	S2—C1—S1—C11	11.5 (3)
C8—C7—N2—C9	123.5 (3)	C12—C11—S1—C1	−67.1 (3)
C10—C9—N2—C2	−111.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···S1i	0.98	2.91	3.893 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯S1i	0.98	2.91	3.893 (4)	177

Symmetry code: (i) .