Triethyl­ammonium 2,4,6-trisulfanylidene-1,3,5-triazinan-1-ide

Li, H.-P.; Ng, S.W.

doi:10.1107/S1600536811034271

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2473

doi:10.1107/S1600536811034271

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Triethylammonium 2,4,6-trisulfanylidene-1,3,5-triazinan-1-ide

He-Ping Li ^a and Seik Weng Ng ^b,^c ^*

^aHenan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 18 August 2011; accepted 21 August 2011; online 27 August 2011)

The asymmetric unit of the title compound, C₆H₁₆N⁺·C₃H₂N₃S₃⁻, contains two independent ion pairs. The 2,4,6-trithioxo-1,3,5-triazinan-1-ide anion features an almost planar six-membered ring (r.m.s. deviations = 0.009 and 0.018 Å) having exocyclic double-bond S atoms. The anions interact by N—H⋯S hydrogen bonds to generate a chain running along [110]. The triethylammonium cations are hydrogen bonded to the anions with the ammonium H atom forming a hydrogen bond to the negatively-charged N atom of the anion. In the crystal structure, both triethylammonium cations are disordered over two orientations with equal occupancies.

Related literature

For trimethylammonium 2,4,6-trithioxo-1,3,5-triazinan-1-ide monohydrate, see: Hou & Yang (2011 ).

Experimental

Crystal data

C₆H₁₆N⁺·C₃H₂N₃S₃⁻
M_r = 278.45
Monoclinic, P 2₁ /n
a = 13.1648 (3) Å
b = 13.0636 (3) Å
c = 16.9552 (4) Å
β = 93.779 (2)°
V = 2909.61 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.828, T_max = 0.908
13126 measured reflections
5978 independent reflections
3218 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.196
S = 1.02
5978 reflections
347 parameters
136 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4	0.88	2.03	2.89 (1)	163
N1′—H1′⋯N4	0.88	2.08	2.95 (1)	166
N2—H2⋯N7	0.88	2.02	2.88 (1)	165
N2′—H2′⋯N7	0.88	2.04	2.89 (1)	163
N3—H3⋯S4	0.88 (1)	2.38 (1)	3.248 (3)	169 (4)
N5—H5⋯S2ⁱ	0.88 (1)	2.44 (1)	3.319 (4)	171 (3)
N6—H6⋯S1	0.87 (1)	2.58 (1)	3.446 (3)	170 (3)
N8—H8⋯S6ⁱⁱ	0.88 (1)	2.47 (2)	3.326 (3)	164 (4)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1.

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034271/xu5300sup1.cif

Supporting information file. DOI: 10.1107/S1600536811034271/xu5300Isup3.cml

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034271/xu5300Isup2.hkl

checkCIF report

Comment top

This study is an extension of a study on the amine salts of 1,3,5-triazinane-2,4,6-trithione (thiocyanuric acid). The previous study described the monohydrated trimethylammonium salt (Hou & Yang, 2011). The triethylammonium analog (Scheme I) does not crystallize with water. Its anion features a planar six-membered ring having exocyclic double-bond S atoms (Fig. 1). The anions interact by N–H···S hydrogen bonds to generate a chain running along [1 1 0] (Table 1). The cations are hydrogen bonded to the anions with the ammonium H forming a hydrogen bond to the negatively-charged N atom of the anion.

Related literature top

For trimethylammonium 2,4,6-trithioxo-1,3,5-triazinan-1-ide monohydrate, see: Hou & Yang (2011).

Experimental top

1,3,5-Triazin-2,4,6-trithione (0.25 mmol, 0.045 g) was dissolved in a water-ethanol (50/100 v/v) mixture. Triethylamine (0.75 mmol, 0.076 g) was added to the solution. The mixture was stirred and then set aside for the growth of colorless crystals, which appeared after several weeks.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent ion-pairs of C₆H₁₆N^.C₃H₂N₃S₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the cations is not shown.

Triethylammonium 2,4,6-trisulfanylidene-1,3,5-triazinan-1-ide top

Crystal data top

C₆H₁₆N⁺·C₃H₂N₃S₃⁻	F(000) = 1184
M_r = 278.45	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2936 reflections
a = 13.1648 (3) Å	θ = 2.5–24.1°
b = 13.0636 (3) Å	µ = 0.49 mm⁻¹
c = 16.9552 (4) Å	T = 293 K
β = 93.779 (2)°	Prism, colorless
V = 2909.61 (12) Å³	0.40 × 0.30 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	5978 independent reflections
Radiation source: fine-focus sealed tube	3218 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 26.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
T_min = 0.828, T_max = 0.908	k = −13→16
13126 measured reflections	l = −21→21

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0954P)² + 0.927P] where P = (F_o² + 2F_c²)/3
5978 reflections	(Δ/σ)_max = 0.001
347 parameters	Δρ_max = 0.41 e Å⁻³
136 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₆H₁₆N⁺·C₃H₂N₃S₃⁻	V = 2909.61 (12) Å³
M_r = 278.45	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.1648 (3) Å	µ = 0.49 mm⁻¹
b = 13.0636 (3) Å	T = 293 K
c = 16.9552 (4) Å	0.40 × 0.30 × 0.20 mm
β = 93.779 (2)°

Data collection top

Bruker SMART APEX diffractometer	5978 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3218 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.908	R_int = 0.026
13126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	136 restraints
wR(F²) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.41 e Å⁻³
5978 reflections	Δρ_min = −0.29 e Å⁻³
347 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.56457 (8)	0.44837 (8)	0.61142 (7)	0.0707 (3)
S2	0.39743 (9)	0.12143 (9)	0.47969 (8)	0.0934 (5)
S3	0.77911 (9)	0.10693 (11)	0.59146 (9)	0.0958 (5)
S4	0.26844 (8)	0.35815 (9)	0.50491 (8)	0.0850 (4)
S5	0.39625 (9)	0.69261 (12)	0.65071 (9)	0.1040 (5)
S6	0.00526 (8)	0.63977 (11)	0.56829 (9)	0.1017 (5)
N1	0.8202 (8)	0.3621 (7)	0.7084 (6)	0.076 (2)	0.50
H1	0.7845	0.3346	0.6682	0.091*	0.50
N1'	0.8362 (8)	0.3333 (8)	0.7120 (6)	0.076 (2)	0.50
H1'	0.7947	0.3129	0.6722	0.091*	0.50
N2	0.1569 (6)	0.8543 (8)	0.6796 (6)	0.1009 (14)	0.50
H2	0.1816	0.8015	0.6550	0.121*	0.50
N2'	0.1547 (6)	0.8603 (8)	0.6708 (6)	0.1009 (14)	0.50
H2'	0.1577	0.8023	0.6447	0.121*	0.50
N3	0.5004 (2)	0.2787 (3)	0.54226 (18)	0.0621 (8)
N4	0.6686 (2)	0.2755 (3)	0.59703 (17)	0.0624 (8)
N5	0.5888 (2)	0.1310 (3)	0.5391 (2)	0.0669 (9)
N6	0.3181 (2)	0.5339 (3)	0.57618 (18)	0.0604 (8)
N7	0.2027 (2)	0.6633 (3)	0.60457 (18)	0.0640 (8)
N8	0.1518 (2)	0.5117 (2)	0.53993 (19)	0.0620 (8)
C1	0.7544 (7)	0.3568 (7)	0.7780 (5)	0.108 (3)	0.50
H1A	0.7888	0.3916	0.8228	0.129*	0.50
H1B	0.6909	0.3924	0.7648	0.129*	0.50
C2	0.7317 (11)	0.2483 (8)	0.8011 (8)	0.121 (4)	0.50
H2A	0.6885	0.2486	0.8445	0.182*	0.50
H2B	0.7942	0.2137	0.8165	0.182*	0.50
H2C	0.6981	0.2134	0.7569	0.182*	0.50
C3	0.9125 (11)	0.2955 (13)	0.7237 (8)	0.122 (3)	0.50
H3A	0.9463	0.3149	0.7740	0.147*	0.50
H3B	0.8904	0.2250	0.7281	0.147*	0.50
C4	0.9878 (11)	0.3016 (15)	0.6613 (7)	0.142 (4)	0.50
H4A	1.0450	0.2583	0.6757	0.213*	0.50
H4B	1.0106	0.3710	0.6566	0.213*	0.50
H4C	0.9561	0.2795	0.6116	0.213*	0.50
C5	0.8420 (11)	0.4699 (8)	0.6851 (7)	0.097 (3)	0.50
H5A	0.7780	0.5064	0.6769	0.117*	0.50
H5B	0.8739	0.4689	0.6351	0.117*	0.50
C6	0.9096 (18)	0.5278 (12)	0.7443 (11)	0.124 (5)	0.50
H6A	0.9188	0.5965	0.7258	0.186*	0.50
H6B	0.9746	0.4944	0.7509	0.186*	0.50
H6C	0.8788	0.5296	0.7940	0.186*	0.50
C7	0.2470 (8)	0.9181 (9)	0.7086 (6)	0.136 (3)	0.50
H7A	0.2235	0.9747	0.7397	0.163*	0.50
H7B	0.2923	0.8766	0.7428	0.163*	0.50
C8	0.3050 (12)	0.9597 (14)	0.6424 (10)	0.203 (6)	0.50
H8A	0.3612	1.0000	0.6638	0.305*	0.50
H8B	0.2608	1.0018	0.6087	0.305*	0.50
H8C	0.3300	0.9040	0.6122	0.305*	0.50
C9	0.0883 (8)	0.9094 (9)	0.6200 (5)	0.119 (3)	0.50
H9A	0.0346	0.8634	0.6005	0.143*	0.50
H9B	0.1270	0.9289	0.5756	0.143*	0.50
C10	0.0415 (12)	1.0034 (10)	0.6533 (10)	0.181 (5)	0.50
H10A	−0.0038	1.0345	0.6136	0.271*	0.50
H10B	0.0942	1.0511	0.6698	0.271*	0.50
H10C	0.0042	0.9848	0.6979	0.271*	0.50
C11	0.0997 (8)	0.8114 (10)	0.7461 (7)	0.143 (4)	0.50
H11A	0.0848	0.8665	0.7819	0.171*	0.50
H11B	0.0354	0.7836	0.7246	0.171*	0.50
C12	0.1574 (12)	0.7292 (13)	0.7917 (10)	0.156 (5)	0.50
H12A	0.1333	0.7246	0.8438	0.234*	0.50
H12B	0.2286	0.7457	0.7955	0.234*	0.50
H12C	0.1471	0.6649	0.7651	0.234*	0.50
C1'	0.8025 (7)	0.2833 (8)	0.7858 (5)	0.108 (3)	0.50
H1'A	0.8058	0.2097	0.7790	0.129*	0.50
H1'B	0.8507	0.3013	0.8293	0.129*	0.50
C2'	0.6989 (8)	0.3099 (11)	0.8085 (8)	0.121 (4)	0.50
H2'A	0.6834	0.2709	0.8541	0.182*	0.50
H2'B	0.6502	0.2944	0.7655	0.182*	0.50
H2'C	0.6960	0.3816	0.8205	0.182*	0.50
C3'	0.9402 (10)	0.2901 (14)	0.6995 (8)	0.122 (3)	0.50
H3'A	0.9880	0.3147	0.7411	0.147*	0.50
H3'B	0.9375	0.2161	0.7033	0.147*	0.50
C4'	0.9777 (12)	0.3186 (15)	0.6218 (7)	0.142 (4)	0.50
H4'A	1.0491	0.3037	0.6218	0.213*	0.50
H4'B	0.9668	0.3903	0.6126	0.213*	0.50
H4'C	0.9415	0.2800	0.5807	0.213*	0.50
C5'	0.8326 (11)	0.4481 (8)	0.7142 (8)	0.097 (3)	0.50
H5'A	0.7668	0.4692	0.7309	0.117*	0.50
H5'B	0.8388	0.4741	0.6611	0.117*	0.50
C6'	0.9144 (17)	0.4957 (12)	0.7684 (12)	0.124 (5)	0.50
H6'A	0.9082	0.5688	0.7663	0.186*	0.50
H6'B	0.9800	0.4759	0.7521	0.186*	0.50
H6'C	0.9072	0.4726	0.8216	0.186*	0.50
C7'	0.2308 (8)	0.9288 (8)	0.6358 (7)	0.136 (3)	0.50
H7'A	0.2105	0.9400	0.5805	0.163*	0.50
H7'B	0.2965	0.8949	0.6387	0.163*	0.50
C8'	0.2415 (14)	1.0306 (9)	0.6767 (11)	0.203 (6)	0.50
H8'A	0.2899	1.0718	0.6510	0.305*	0.50
H8'B	0.2647	1.0203	0.7310	0.305*	0.50
H8'C	0.1767	1.0646	0.6741	0.305*	0.50
C9'	0.0469 (7)	0.8951 (10)	0.6579 (6)	0.119 (3)	0.50
H9'A	0.0363	0.9524	0.6929	0.143*	0.50
H9'B	0.0025	0.8400	0.6726	0.143*	0.50
C10'	0.0164 (11)	0.9271 (14)	0.5749 (7)	0.181 (5)	0.50
H10D	−0.0533	0.9490	0.5716	0.271*	0.50
H10E	0.0241	0.8703	0.5399	0.271*	0.50
H10F	0.0590	0.9825	0.5600	0.271*	0.50
C11'	0.1796 (9)	0.8327 (10)	0.7566 (6)	0.143 (4)	0.50
H11C	0.2496	0.8095	0.7636	0.171*	0.50
H11D	0.1723	0.8927	0.7895	0.171*	0.50
C12'	0.1092 (12)	0.7493 (13)	0.7816 (10)	0.156 (5)	0.50
H12D	0.1256	0.7323	0.8360	0.234*	0.50
H12E	0.1172	0.6897	0.7494	0.234*	0.50
H12F	0.0400	0.7727	0.7753	0.234*	0.50
C13	0.5803 (3)	0.3276 (3)	0.5823 (2)	0.0592 (9)
C14	0.5002 (3)	0.1797 (3)	0.5217 (2)	0.0636 (10)
C15	0.6742 (3)	0.1784 (3)	0.5752 (2)	0.0640 (10)
C16	0.2983 (3)	0.6290 (3)	0.6081 (2)	0.0633 (10)
C17	0.1280 (3)	0.6037 (3)	0.5719 (2)	0.0641 (10)
C18	0.2463 (3)	0.4720 (3)	0.5414 (2)	0.0573 (9)
H3	0.4412 (16)	0.309 (3)	0.532 (2)	0.075 (12)*
H5	0.589 (3)	0.0647 (10)	0.529 (2)	0.058 (11)*
H6	0.3782 (15)	0.506 (3)	0.581 (2)	0.071 (12)*
H8	0.101 (2)	0.475 (3)	0.519 (2)	0.093 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0648 (6)	0.0647 (7)	0.0806 (7)	−0.0049 (5)	−0.0096 (5)	−0.0097 (6)
S2	0.0712 (7)	0.0719 (8)	0.1298 (11)	0.0086 (5)	−0.0474 (7)	−0.0257 (7)
S3	0.0604 (7)	0.1016 (10)	0.1215 (10)	0.0198 (6)	−0.0237 (6)	−0.0220 (8)
S4	0.0596 (6)	0.0703 (8)	0.1218 (10)	0.0075 (5)	−0.0196 (6)	−0.0299 (7)
S5	0.0692 (7)	0.1147 (11)	0.1265 (11)	−0.0177 (7)	−0.0060 (7)	−0.0590 (9)
S6	0.0572 (6)	0.1002 (10)	0.1459 (12)	0.0125 (6)	−0.0065 (7)	−0.0554 (9)
N1	0.066 (3)	0.081 (5)	0.077 (2)	−0.008 (3)	−0.023 (2)	−0.001 (3)
N1'	0.066 (3)	0.081 (5)	0.077 (2)	−0.008 (3)	−0.023 (2)	−0.001 (3)
N2	0.115 (3)	0.091 (3)	0.099 (3)	0.003 (3)	0.028 (3)	−0.028 (3)
N2'	0.115 (3)	0.091 (3)	0.099 (3)	0.003 (3)	0.028 (3)	−0.028 (3)
N3	0.0509 (18)	0.063 (2)	0.071 (2)	0.0060 (15)	−0.0113 (15)	−0.0105 (17)
N4	0.0521 (17)	0.071 (2)	0.0620 (18)	0.0003 (15)	−0.0100 (13)	−0.0100 (17)
N5	0.0577 (19)	0.061 (2)	0.079 (2)	0.0062 (16)	−0.0188 (16)	−0.0142 (18)
N6	0.0460 (17)	0.070 (2)	0.0646 (19)	0.0004 (15)	−0.0022 (14)	−0.0133 (17)
N7	0.0582 (18)	0.070 (2)	0.0633 (19)	−0.0020 (16)	0.0029 (14)	−0.0212 (17)
N8	0.0449 (17)	0.062 (2)	0.078 (2)	−0.0008 (15)	−0.0038 (15)	−0.0179 (18)
C1	0.107 (6)	0.122 (7)	0.089 (4)	−0.013 (5)	−0.027 (4)	0.003 (5)
C2	0.120 (7)	0.143 (9)	0.102 (5)	−0.014 (6)	0.013 (5)	0.005 (7)
C3	0.117 (7)	0.106 (5)	0.137 (8)	0.007 (5)	−0.041 (5)	−0.003 (6)
C4	0.185 (7)	0.155 (7)	0.094 (8)	−0.018 (5)	0.071 (7)	0.015 (7)
C5	0.086 (4)	0.096 (6)	0.107 (8)	−0.026 (4)	−0.011 (5)	0.031 (5)
C6	0.125 (5)	0.114 (8)	0.130 (9)	−0.035 (6)	−0.001 (6)	−0.013 (7)
C7	0.142 (6)	0.122 (6)	0.146 (7)	0.014 (5)	0.018 (7)	−0.042 (7)
C8	0.203 (9)	0.183 (9)	0.225 (9)	−0.031 (8)	0.034 (8)	−0.022 (8)
C9	0.122 (7)	0.108 (5)	0.127 (7)	0.018 (6)	0.005 (5)	−0.028 (6)
C10	0.168 (8)	0.164 (8)	0.210 (9)	0.045 (7)	0.002 (7)	−0.015 (7)
C11	0.150 (8)	0.158 (7)	0.125 (6)	0.013 (7)	0.049 (7)	−0.044 (6)
C12	0.182 (10)	0.164 (8)	0.126 (6)	0.042 (8)	0.043 (8)	−0.010 (6)
C1'	0.107 (6)	0.122 (7)	0.089 (4)	−0.013 (5)	−0.027 (4)	0.003 (5)
C2'	0.120 (7)	0.143 (9)	0.102 (5)	−0.014 (6)	0.013 (5)	0.005 (7)
C3'	0.117 (7)	0.106 (5)	0.137 (8)	0.007 (5)	−0.041 (5)	−0.003 (6)
C4'	0.185 (7)	0.155 (7)	0.094 (8)	−0.018 (5)	0.071 (7)	0.015 (7)
C5'	0.086 (4)	0.096 (6)	0.107 (8)	−0.026 (4)	−0.011 (5)	0.031 (5)
C6'	0.125 (5)	0.114 (8)	0.130 (9)	−0.035 (6)	−0.001 (6)	−0.013 (7)
C7'	0.142 (6)	0.122 (6)	0.146 (7)	0.014 (5)	0.018 (7)	−0.042 (7)
C8'	0.203 (9)	0.183 (9)	0.225 (9)	−0.031 (8)	0.034 (8)	−0.022 (8)
C9'	0.122 (7)	0.108 (5)	0.127 (7)	0.018 (6)	0.005 (5)	−0.028 (6)
C10'	0.168 (8)	0.164 (8)	0.210 (9)	0.045 (7)	0.002 (7)	−0.015 (7)
C11'	0.150 (8)	0.158 (7)	0.125 (6)	0.013 (7)	0.049 (7)	−0.044 (6)
C12'	0.182 (10)	0.164 (8)	0.126 (6)	0.042 (8)	0.043 (8)	−0.010 (6)
C13	0.051 (2)	0.075 (3)	0.051 (2)	−0.0053 (18)	−0.0031 (15)	−0.0016 (19)
C14	0.060 (2)	0.067 (3)	0.061 (2)	0.0059 (18)	−0.0141 (17)	−0.007 (2)
C15	0.052 (2)	0.078 (3)	0.060 (2)	0.0025 (18)	−0.0090 (16)	−0.009 (2)
C16	0.062 (2)	0.074 (3)	0.054 (2)	−0.0113 (19)	0.0054 (17)	−0.016 (2)
C17	0.057 (2)	0.070 (3)	0.064 (2)	−0.0033 (19)	0.0018 (18)	−0.013 (2)
C18	0.052 (2)	0.060 (2)	0.059 (2)	−0.0046 (17)	−0.0047 (16)	−0.0050 (18)

Geometric parameters (Å, º) top

S1—C13	1.669 (4)	C6—H6C	0.9600
S2—C14	1.670 (4)	C7—C8	1.501 (5)
S3—C15	1.675 (4)	C7—H7A	0.9700
S4—C18	1.645 (4)	C7—H7B	0.9700
S5—C16	1.659 (4)	C8—H8A	0.9600
S6—C17	1.681 (4)	C8—H8B	0.9600
N1—C5	1.496 (5)	C8—H8C	0.9600
N1—C3	1.502 (5)	C9—C10	1.501 (5)
N1—C1	1.511 (5)	C9—H9A	0.9700
N1—H1	0.8800	C9—H9B	0.9700
N1'—C5'	1.501 (5)	C10—H10A	0.9600
N1'—C1'	1.505 (5)	C10—H10B	0.9600
N1'—C3'	1.508 (5)	C10—H10C	0.9600
N1'—H1'	0.8800	C11—C12	1.499 (5)
N2—C9	1.495 (5)	C11—H11A	0.9700
N2—C11	1.505 (5)	C11—H11B	0.9700
N2—C7	1.505 (5)	C12—H12A	0.9600
N2—H2	0.8800	C12—H12B	0.9600
N2'—C9'	1.493 (5)	C12—H12C	0.9600
N2'—C7'	1.494 (5)	C1'—C2'	1.482 (5)
N2'—C11'	1.514 (5)	C1'—H1'A	0.9700
N2'—H2'	0.8800	C1'—H1'B	0.9700
N3—C14	1.339 (5)	C2'—H2'A	0.9600
N3—C13	1.373 (4)	C2'—H2'B	0.9600
N3—H3	0.881 (10)	C2'—H2'C	0.9600
N4—C15	1.325 (5)	C3'—C4'	1.484 (5)
N4—C13	1.356 (4)	C3'—H3'A	0.9700
N5—C14	1.345 (4)	C3'—H3'B	0.9700
N5—C15	1.389 (4)	C4'—H4'A	0.9600
N5—H5	0.883 (10)	C4'—H4'B	0.9600
N6—C18	1.350 (4)	C4'—H4'C	0.9600
N6—C16	1.387 (5)	C5'—C6'	1.504 (5)
N6—H6	0.873 (10)	C5'—H5'A	0.9700
N7—C16	1.333 (5)	C5'—H5'B	0.9700
N7—C17	1.345 (5)	C6'—H6'A	0.9600
N8—C18	1.347 (5)	C6'—H6'B	0.9600
N8—C17	1.362 (5)	C6'—H6'C	0.9600
N8—H8	0.881 (10)	C7'—C8'	1.501 (5)
C1—C2	1.506 (5)	C7'—H7'A	0.9700
C1—H1A	0.9700	C7'—H7'B	0.9700
C1—H1B	0.9700	C8'—H8'A	0.9600
C2—H2A	0.9600	C8'—H8'B	0.9600
C2—H2B	0.9600	C8'—H8'C	0.9600
C2—H2C	0.9600	C9'—C10'	1.498 (5)
C3—C4	1.500 (5)	C9'—H9'A	0.9700
C3—H3A	0.9700	C9'—H9'B	0.9700
C3—H3B	0.9700	C10'—H10D	0.9600
C4—H4A	0.9600	C10'—H10E	0.9600
C4—H4B	0.9600	C10'—H10F	0.9600
C4—H4C	0.9600	C11'—C12'	1.510 (5)
C5—C6	1.502 (5)	C11'—H11C	0.9700
C5—H5A	0.9700	C11'—H11D	0.9700
C5—H5B	0.9700	C12'—H12D	0.9600
C6—H6A	0.9600	C12'—H12E	0.9600
C6—H6B	0.9600	C12'—H12F	0.9600

C5—N1—C3	115.1 (6)	N2—C11—H11A	109.0
C5—N1—C1	112.3 (6)	C12—C11—H11B	109.0
C3—N1—C1	109.7 (6)	N2—C11—H11B	109.0
C5—N1—H1	106.4	H11A—C11—H11B	107.8
C3—N1—H1	106.4	C11—C12—H12A	109.5
C1—N1—H1	106.4	C11—C12—H12B	109.5
C5'—N1'—C1'	113.7 (6)	H12A—C12—H12B	109.5
C5'—N1'—C3'	114.1 (7)	C11—C12—H12C	109.5
C1'—N1'—C3'	106.0 (5)	H12A—C12—H12C	109.5
C5'—N1'—H1'	107.6	H12B—C12—H12C	109.5
C1'—N1'—H1'	107.6	C2'—C1'—N1'	116.2 (7)
C3'—N1'—H1'	107.6	C2'—C1'—H1'A	108.2
C9—N2—C11	112.1 (6)	N1'—C1'—H1'A	108.2
C9—N2—C7	112.5 (6)	C2'—C1'—H1'B	108.2
C11—N2—C7	112.6 (7)	N1'—C1'—H1'B	108.2
C9—N2—H2	106.4	H1'A—C1'—H1'B	107.4
C11—N2—H2	106.4	C1'—C2'—H2'A	109.5
C7—N2—H2	106.4	C1'—C2'—H2'B	109.5
C9'—N2'—C7'	114.6 (6)	H2'A—C2'—H2'B	109.5
C9'—N2'—C11'	110.9 (6)	C1'—C2'—H2'C	109.5
C7'—N2'—C11'	114.6 (6)	H2'A—C2'—H2'C	109.5
C9'—N2'—H2'	105.3	H2'B—C2'—H2'C	109.5
C7'—N2'—H2'	105.3	C4'—C3'—N1'	112.9 (7)
C11'—N2'—H2'	105.3	C4'—C3'—H3'A	109.0
C14—N3—C13	124.6 (3)	N1'—C3'—H3'A	109.0
C14—N3—H3	113 (3)	C4'—C3'—H3'B	109.0
C13—N3—H3	122 (3)	N1'—C3'—H3'B	109.0
C15—N4—C13	119.5 (3)	H3'A—C3'—H3'B	107.8
C14—N5—C15	123.4 (4)	C3'—C4'—H4'A	109.5
C14—N5—H5	115 (2)	C3'—C4'—H4'B	109.5
C15—N5—H5	121 (2)	H4'A—C4'—H4'B	109.5
C18—N6—C16	124.2 (3)	C3'—C4'—H4'C	109.5
C18—N6—H6	113 (3)	H4'A—C4'—H4'C	109.5
C16—N6—H6	123 (3)	H4'B—C4'—H4'C	109.5
C16—N7—C17	119.1 (3)	N1'—C5'—C6'	113.9 (7)
C18—N8—C17	124.6 (3)	N1'—C5'—H5'A	108.8
C18—N8—H8	118 (3)	C6'—C5'—H5'A	108.8
C17—N8—H8	117 (3)	N1'—C5'—H5'B	108.8
C2—C1—N1	112.3 (6)	C6'—C5'—H5'B	108.8
C2—C1—H1A	109.1	H5'A—C5'—H5'B	107.7
N1—C1—H1A	109.1	C5'—C6'—H6'A	109.5
C2—C1—H1B	109.1	C5'—C6'—H6'B	109.5
N1—C1—H1B	109.1	H6'A—C6'—H6'B	109.5
H1A—C1—H1B	107.9	C5'—C6'—H6'C	109.5
C1—C2—H2A	109.5	H6'A—C6'—H6'C	109.5
C1—C2—H2B	109.5	H6'B—C6'—H6'C	109.5
H2A—C2—H2B	109.5	N2'—C7'—C8'	113.1 (7)
C1—C2—H2C	109.5	N2'—C7'—H7'A	109.0
H2A—C2—H2C	109.5	C8'—C7'—H7'A	109.0
H2B—C2—H2C	109.5	N2'—C7'—H7'B	109.0
C4—C3—N1	114.3 (7)	C8'—C7'—H7'B	109.0
C4—C3—H3A	108.7	H7'A—C7'—H7'B	107.8
N1—C3—H3A	108.7	C7'—C8'—H8'A	109.5
C4—C3—H3B	108.7	C7'—C8'—H8'B	109.5
N1—C3—H3B	108.7	H8'A—C8'—H8'B	109.5
H3A—C3—H3B	107.6	C7'—C8'—H8'C	109.5
C3—C4—H4A	109.5	H8'A—C8'—H8'C	109.5
C3—C4—H4B	109.5	H8'B—C8'—H8'C	109.5
H4A—C4—H4B	109.5	N2'—C9'—C10'	114.5 (7)
C3—C4—H4C	109.5	N2'—C9'—H9'A	108.6
H4A—C4—H4C	109.5	C10'—C9'—H9'A	108.6
H4B—C4—H4C	109.5	N2'—C9'—H9'B	108.6
N1—C5—C6	114.4 (7)	C10'—C9'—H9'B	108.6
N1—C5—H5A	108.7	H9'A—C9'—H9'B	107.6
C6—C5—H5A	108.7	C9'—C10'—H10D	109.5
N1—C5—H5B	108.7	C9'—C10'—H10E	109.5
C6—C5—H5B	108.7	H10D—C10'—H10E	109.5
H5A—C5—H5B	107.6	C9'—C10'—H10F	109.5
C5—C6—H6A	109.5	H10D—C10'—H10F	109.5
C5—C6—H6B	109.5	H10E—C10'—H10F	109.5
H6A—C6—H6B	109.5	C12'—C11'—N2'	110.1 (7)
C5—C6—H6C	109.5	C12'—C11'—H11C	109.6
H6A—C6—H6C	109.5	N2'—C11'—H11C	109.6
H6B—C6—H6C	109.5	C12'—C11'—H11D	109.6
C8—C7—N2	112.6 (7)	N2'—C11'—H11D	109.6
C8—C7—H7A	109.1	H11C—C11'—H11D	108.1
N2—C7—H7A	109.1	C11'—C12'—H12D	109.5
C8—C7—H7B	109.1	C11'—C12'—H12E	109.5
N2—C7—H7B	109.1	H12D—C12'—H12E	109.5
H7A—C7—H7B	107.8	C11'—C12'—H12F	109.5
C7—C8—H8A	109.5	H12D—C12'—H12F	109.5
C7—C8—H8B	109.5	H12E—C12'—H12F	109.5
H8A—C8—H8B	109.5	N4—C13—N3	118.5 (4)
C7—C8—H8C	109.5	N4—C13—S1	122.8 (3)
H8A—C8—H8C	109.5	N3—C13—S1	118.7 (3)
H8B—C8—H8C	109.5	N3—C14—N5	114.4 (3)
N2—C9—C10	112.6 (7)	N3—C14—S2	122.6 (3)
N2—C9—H9A	109.1	N5—C14—S2	123.0 (3)
C10—C9—H9A	109.1	N4—C15—N5	119.5 (3)
N2—C9—H9B	109.1	N4—C15—S3	123.2 (3)
C10—C9—H9B	109.1	N5—C15—S3	117.3 (3)
H9A—C9—H9B	107.8	N7—C16—N6	119.0 (3)
C9—C10—H10A	109.5	N7—C16—S5	123.8 (3)
C9—C10—H10B	109.5	N6—C16—S5	117.2 (3)
H10A—C10—H10B	109.5	N7—C17—N8	119.6 (3)
C9—C10—H10C	109.5	N7—C17—S6	121.8 (3)
H10A—C10—H10C	109.5	N8—C17—S6	118.6 (3)
H10B—C10—H10C	109.5	N8—C18—N6	113.4 (3)
C12—C11—N2	113.1 (7)	N8—C18—S4	121.9 (3)
C12—C11—H11A	109.0	N6—C18—S4	124.7 (3)

C5—N1—C1—C2	179.5 (10)	C15—N4—C13—N3	−2.5 (5)
C3—N1—C1—C2	−51.2 (14)	C15—N4—C13—S1	177.1 (3)
C5—N1—C3—C4	−47.4 (19)	C14—N3—C13—N4	5.6 (6)
C1—N1—C3—C4	−175.2 (16)	C14—N3—C13—S1	−174.1 (3)
C3—N1—C5—C6	−58.1 (17)	C13—N3—C14—N5	−4.0 (6)
C1—N1—C5—C6	68.3 (15)	C13—N3—C14—S2	174.7 (3)
C9—N2—C7—C8	−53.0 (15)	C15—N5—C14—N3	−0.2 (6)
C11—N2—C7—C8	179.2 (12)	C15—N5—C14—S2	−179.0 (3)
C11—N2—C9—C10	65.1 (13)	C13—N4—C15—N5	−1.4 (6)
C7—N2—C9—C10	−62.9 (13)	C13—N4—C15—S3	−179.3 (3)
C9—N2—C11—C12	161.5 (13)	C14—N5—C15—N4	2.9 (6)
C7—N2—C11—C12	−70.5 (15)	C14—N5—C15—S3	−179.1 (3)
C5'—N1'—C1'—C2'	56.9 (13)	C17—N7—C16—N6	1.6 (6)
C3'—N1'—C1'—C2'	−177.0 (12)	C17—N7—C16—S5	−176.9 (3)
C5'—N1'—C3'—C4'	−63.6 (18)	C18—N6—C16—N7	−0.3 (6)
C1'—N1'—C3'—C4'	170.6 (16)	C18—N6—C16—S5	178.3 (3)
C1'—N1'—C5'—C6'	72.4 (15)	C16—N7—C17—N8	−2.9 (6)
C3'—N1'—C5'—C6'	−49.3 (16)	C16—N7—C17—S6	177.7 (3)
C9'—N2'—C7'—C8'	68.6 (15)	C18—N8—C17—N7	3.2 (6)
C11'—N2'—C7'—C8'	−61.2 (15)	C18—N8—C17—S6	−177.4 (3)
C7'—N2'—C9'—C10'	46.7 (15)	C17—N8—C18—N6	−1.9 (6)
C11'—N2'—C9'—C10'	178.3 (12)	C17—N8—C18—S4	177.3 (3)
C9'—N2'—C11'—C12'	58.6 (14)	C16—N6—C18—N8	0.4 (5)
C7'—N2'—C11'—C12'	−169.8 (11)	C16—N6—C18—S4	−178.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.88	2.03	2.89 (1)	163
N1′—H1′···N4	0.88	2.08	2.95 (1)	166
N2—H2···N7	0.88	2.02	2.88 (1)	165
N2′—H2′···N7	0.88	2.04	2.89 (1)	163
N3—H3···S4	0.88 (1)	2.38 (1)	3.248 (3)	169 (4)
N5—H5···S2ⁱ	0.88 (1)	2.44 (1)	3.319 (4)	171 (3)
N6—H6···S1	0.87 (1)	2.58 (1)	3.446 (3)	170 (3)
N8—H8···S6ⁱⁱ	0.88 (1)	2.47 (2)	3.326 (3)	164 (4)

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

Experimental details

Crystal data
Chemical formula	C₆H₁₆N⁺·C₃H₂N₃S₃⁻
M_r	278.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.1648 (3), 13.0636 (3), 16.9552 (4)
β (°)	93.779 (2)
V (Å³)	2909.61 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.828, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	13126, 5978, 3218
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.196, 1.02
No. of reflections	5978
No. of parameters	347
No. of restraints	136
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.88	2.03	2.89 (1)	163
N1'—H1'···N4	0.88	2.08	2.95 (1)	166
N2—H2···N7	0.88	2.02	2.88 (1)	165
N2'—H2'···N7	0.88	2.04	2.89 (1)	163
N3—H3···S4	0.88 (1)	2.38 (1)	3.248 (3)	169 (4)
N5—H5···S2ⁱ	0.88 (1)	2.44 (1)	3.319 (4)	171 (3)
N6—H6···S1	0.87 (1)	2.58 (1)	3.446 (3)	170 (3)
N8—H8···S6ⁱⁱ	0.88 (1)	2.47 (2)	3.326 (3)	164 (4)

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

Acknowledgements

We thank Henan University of Traditional Medicine and the University of Malaya for supporting this study.

References

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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