3,3′-(Hexane-1,6-di­yl)bis­(1-vinyl-4-imidazoline-2-thione)

Partl, G.; Laus, G.; Kahlenberg, V.; Huppertz, H.; Schottenberger, H.

doi:10.1107/S2414314617005995

organic compounds

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ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170599

https://doi.org/10.1107/S2414314617005995

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3,3′-(Hexane-1,6-diyl)bis(1-vinyl-4-imidazoline-2-thione)

Gabriel Partl,^a Gerhard Laus,^a Volker Kahlenberg,^b Hubert Huppertz ^a and Herwig Schottenberger ^a ^*

^aUniversity of Innsbruck, Faculty of Chemistry and Pharmacy, Innrain 80, 6020 Innsbruck, Austria, and ^bUniversity of Innsbruck, Institute of Mineralogy and Petrography, Innrain 52, 6020 Innsbruck, Austria
^*Correspondence e-mail: herwig.schottenberger@uibk.ac.at

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 13 April 2017; accepted 20 April 2017; online 28 April 2017)

The title compound, C₁₆H₂₂N₄S₂, was obtained by the reaction of sulfur with the corresponding quaternary salt in the presence of K₂CO₃. It crystallizes with two half-molecules in the asymmetric unit; the complete molecules are generated by inversion symmetry with the central CH₂—CH₂ bonds of the hexane bridges being located on inversion centres. In each molecule, the C₆-alkyl chain adopts a typical antiperiplanar conformation and the two heterocyclic rings are oriented antiparallel to each other. In the crystal, molecules are linked by C—H⋯π interactions, forming layers lying parallel to the ac plane.

Keywords: crystal structure; cross-linker; imidazole; poly(ionic liquid); thione; vinyl; C—H⋯π interactions.

CCDC reference: 1545075

Structure description

The title compound was obtained from 3,3′-(hexane-1,6-diyl)bis(1-vinylimidazolium) dibromide (Cui et al., 2014 ) by reaction with elemental sulfur in the presence of K₂CO₃. Imidazoline-2-thiones (Laus et al., 2013 ) are versatile building blocks whose properties have been reviewed by Trzhtsinskaya & Abramova (1991 ). The crucial advantages of these thiones are simple synthesis and simple derivation in the realm of imidazole chemistry, a mainstay of ionic liquid research. A field of current relevance, poly(ionic liquids) are macromolecules derived from organic salts which are liquid below 373 K (Yuan & Antonietti, 2011 ). The vinyl substituent renders the title molecule polymerizable, and the bidentate nature of the molecule facilitates cross-linking, thus giving access to a plethora of functionalized imidazolium-containing polymers (Anderson & Long, 2010 ). They in turn offer a multitude of applications and represent major advances in materials science.

The unit cell contains two independent half-molecules (Fig. 1), which are completed by inversion symmetry. The centres of symmetry lie at the mid-point of the (CH₂)₆ spacer between the two imidazoline-2-thione rings. As in other bridged bis(imidazoline-2-thiones), the C₆-alkyl chain adopts a typical antiperiplanar conformation (Bhabak et al., 2011 ; Beheshti et al., 2016 ), and the two heterocyclic rings are oriented antiparallel to each other, as can be seen in Fig. 1. The lengths of the C=S bonds are 1.680 (1) and 1.682 (1) Å, in perfect accordance with the mean value (Laus et al., 2013) in the Cambridge Structural Database (Groom et al., 2016 ). Related structures have been reported with short methylene or ethylene bridges (Liu et al., 2003 ; Jia et al., 2008 ), C₃-to-C₅ bridges (Bhabak et al., 2011; Beheshti et al., 2016), and longer linkers (Marshall et al., 2005 ; Marshall & Harrison, 2007 ).

Figure 1
A view of the molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level. The unlabelled atoms are related to the labelled atoms by symmetry operations (−x + 1, −y + 1, −z + 2) for molecule A and (−x, −y + 1, −z + 1) for molecule B.

In the crystal, molecules are linked by C—H⋯π interactions, forming layers lying parallel to the ac plane (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and N3/N4/C9–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg2ⁱ	0.99	2.75	3.628 (2)	148
C15—H15B⋯Cg1ⁱⁱ	0.99	2.76	3.589 (2)	142
Symmetry codes: (i) x, y, z+1; (ii) -x, -y+1, -z+1.

Figure 2
A view along the b axis of the crystal packing of the title compound, (colour code: blue A molecules, red B molecules). The C—H⋯π interactions are shown as dashed lines, and only H atoms H8B and H15B (blue and red balls, respectively) have been included.

Synthesis and crystallization

A mixture of 3,3′-(hexane-1,6-diyl)bis(1-vinylimidazolium) dibromide (55.6 g, 129 mmol), sulfur (8.25 g, 257 mmol) and K₂CO₃ (35.6 g, 257 mmol) in MeOH (200 ml) was refluxed for 3 h. After evaporation of the solvent under reduced pressure, the residue was extracted with hot CHCl₃ (3 × 250 ml), followed by hot filtration and evaporation of the solvent. To the residue, EtOH (200 ml) was added and the mixture was ultrasonicated for 30 min. The product was collected by filtration and dried in high vacuum for 24 h (yield 40.0 g, 93%; m.p. 423 K). Single crystals were obtained by slow evaporation of a CHCl₃ solution. ¹H NMR (300 MHz, CDCl₃): δ 1.29 (m, 4H), 1.68 (m, 4H), 3.92 (t, J = 7.4 Hz, 4H), 4.80 (dd, J = 9.0, 1.8 Hz, 2H), 5.05 (dd, J = 16.1, 1.8 Hz, 2H), 6.68 (d, J = 2.6 Hz, 2H), 6.91 (d, J = 2.6 Hz, 2H), 7.44 (dd, J = 16.1, 9.0 Hz, 2H) p.p.m. ¹³C NMR (75 MHz, CDCl₃): δ 25.7, 28.2, 47.2, 100.6, 112.4, 118.1, 130.0, 162.3 p.p.m. IR (neat): ν 3126, 3092, 2943, 2855, 1639, 1454, 1421, 1401, 1363, 1288, 1259, 1233, 1160, 975, 875, 831, 762, 742, 718, 697, 659, 518, 486 cm⁻¹.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₂₂N₄S₂
M_r	334.5
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	7.1335 (5), 10.6863 (5), 11.8830 (6)
α, β, γ (°)	99.856 (4), 93.530 (5), 101.937 (5)
V (Å³)	868.75 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.31
Crystal size (mm)	0.54 × 0.2 × 0.14

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini ultra
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.880, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	5545, 3151, 2821
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.072, 1.05
No. of reflections	3151
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20
Computer programs: (CrysAlis PRO; Agilent, 2014), SIR2002 (Burla et al., 2003 ), Mercury (Macrae et al., 2008 ), WinGX (Farrugia, 2012 ), SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1545075

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617005995/su4149sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005995/su4149Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005995/su4149Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005995/su4149Isup4.cml

checkCIF report

Computing details top

Data collection: (CrysAlis PRO; Agilent, 2014); cell refinement: (CrysAlis PRO; Agilent, 2014); data reduction: (CrysAlis PRO; Agilent, 2014); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

3,3'-(Hexane-1,6-diyl)bis(1-vinyl-4-imidazoline-2-thione) top

Crystal data top

C₁₆H₂₂N₄S₂	Z = 2
M_r = 334.5	F(000) = 356
Triclinic, P1	D_x = 1.279 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1335 (5) Å	Cell parameters from 3343 reflections
b = 10.6863 (5) Å	θ = 4.0–28.5°
c = 11.8830 (6) Å	µ = 0.31 mm⁻¹
α = 99.856 (4)°	T = 173 K
β = 93.530 (5)°	Prismatic fragment, colourless
γ = 101.937 (5)°	0.54 × 0.2 × 0.14 mm
V = 868.75 (9) Å³

Data collection top

Agilent Xcalibur Ruby Gemini ultra diffractometer	3151 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 10.3575 pixels mm^-1	θ_max = 25.4°, θ_min = 3.5°
ω scans	h = −6→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→11
T_min = 0.880, T_max = 1	l = −14→13
5545 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0287P)² + 0.3242P] where P = (F_o² + 2F_c²)/3
3151 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.42181 (5)	0.23294 (4)	0.56557 (3)	0.03198 (11)
S2	−0.05723 (5)	0.23677 (4)	0.07703 (3)	0.03264 (11)
N4	0.22259 (16)	0.40254 (11)	0.23089 (10)	0.0230 (3)
N3	0.28775 (16)	0.21338 (11)	0.17699 (10)	0.0234 (3)
N2	0.16867 (17)	0.19534 (11)	0.72562 (10)	0.0237 (3)
N1	0.02845 (16)	0.16137 (10)	0.55287 (10)	0.0216 (2)
C1	0.20569 (19)	0.19571 (12)	0.61534 (11)	0.0212 (3)
C14	0.1222 (2)	0.50945 (14)	0.24615 (12)	0.0270 (3)
H14A	0.0525	0.5112	0.172	0.032*
H14B	0.2178	0.593	0.2699	0.032*
C9	0.15171 (19)	0.28462 (13)	0.16221 (11)	0.0231 (3)
C7	0.3279 (2)	0.37721 (14)	0.87953 (12)	0.0268 (3)
H7A	0.2061	0.3851	0.9129	0.032*
H7B	0.3436	0.4314	0.8195	0.032*
C8	0.4943 (2)	0.42931 (14)	0.97290 (12)	0.0269 (3)
H8A	0.6164	0.422	0.9397	0.032*
H8B	0.479	0.3754	1.0331	0.032*
C11	0.3978 (2)	0.40436 (14)	0.28805 (12)	0.0263 (3)
H11	0.475	0.4756	0.3414	0.032*
C10	0.4393 (2)	0.28843 (14)	0.25507 (12)	0.0268 (3)
H10	0.5515	0.262	0.2802	0.032*
C15	−0.0198 (2)	0.49571 (14)	0.33577 (12)	0.0252 (3)
H15A	−0.1108	0.41	0.3133	0.03*
H15B	−0.0952	0.5638	0.3362	0.03*
C12	0.2730 (2)	0.08475 (14)	0.11905 (13)	0.0279 (3)
H12	0.1562	0.0426	0.0729	0.033*
C13	0.4068 (3)	0.01920 (17)	0.12376 (17)	0.0465 (5)
H13A	0.5258	0.0579	0.169	0.056*
H13B	0.3857	−0.0675	0.082	0.056*
C16	0.07338 (19)	0.50680 (13)	0.45661 (12)	0.0240 (3)
H16A	0.1478	0.4383	0.457	0.029*
H16B	0.1645	0.5924	0.4796	0.029*
C6	0.3136 (2)	0.23646 (14)	0.82447 (12)	0.0292 (3)
H6A	0.4403	0.2258	0.7997	0.035*
H6B	0.2797	0.1803	0.8817	0.035*
C5	−0.1648 (2)	0.12107 (15)	0.37121 (14)	0.0354 (4)
H5A	−0.2801	0.1019	0.407	0.042*
H5B	−0.1707	0.1173	0.2906	0.042*
C3	−0.0276 (2)	0.16310 (14)	0.73221 (13)	0.0287 (3)
H3	−0.0894	0.1575	0.8003	0.034*
C2	−0.1148 (2)	0.14119 (14)	0.62602 (13)	0.0275 (3)
H2	−0.2497	0.1164	0.6044	0.033*
C4	0.0022 (2)	0.15270 (13)	0.43297 (12)	0.0260 (3)
H4	0.1142	0.1712	0.3941	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02078 (19)	0.0399 (2)	0.0333 (2)	0.00365 (15)	0.00389 (15)	0.00479 (17)
S2	0.0251 (2)	0.0409 (2)	0.0281 (2)	0.00743 (16)	−0.00448 (15)	−0.00125 (16)
N4	0.0222 (6)	0.0255 (6)	0.0207 (6)	0.0046 (5)	0.0047 (5)	0.0026 (5)
N3	0.0205 (6)	0.0255 (6)	0.0233 (6)	0.0037 (5)	0.0020 (5)	0.0037 (5)
N2	0.0252 (6)	0.0235 (6)	0.0210 (6)	0.0047 (5)	−0.0004 (5)	0.0025 (5)
N1	0.0202 (6)	0.0207 (6)	0.0229 (6)	0.0043 (4)	−0.0004 (5)	0.0027 (4)
C1	0.0229 (7)	0.0174 (6)	0.0227 (7)	0.0053 (5)	−0.0008 (5)	0.0018 (5)
C14	0.0310 (8)	0.0257 (7)	0.0262 (7)	0.0091 (6)	0.0047 (6)	0.0059 (6)
C9	0.0224 (7)	0.0277 (7)	0.0194 (7)	0.0041 (6)	0.0060 (5)	0.0052 (5)
C7	0.0282 (7)	0.0297 (8)	0.0209 (7)	0.0040 (6)	−0.0020 (6)	0.0048 (6)
C8	0.0273 (7)	0.0335 (8)	0.0188 (7)	0.0041 (6)	−0.0005 (6)	0.0059 (6)
C11	0.0217 (7)	0.0307 (8)	0.0227 (7)	0.0000 (6)	0.0014 (6)	0.0023 (6)
C10	0.0212 (7)	0.0310 (8)	0.0265 (8)	0.0038 (6)	−0.0011 (6)	0.0045 (6)
C15	0.0248 (7)	0.0248 (7)	0.0265 (7)	0.0084 (6)	0.0035 (6)	0.0020 (6)
C12	0.0269 (8)	0.0253 (7)	0.0289 (8)	0.0019 (6)	0.0024 (6)	0.0029 (6)
C13	0.0357 (9)	0.0348 (9)	0.0623 (12)	0.0109 (7)	−0.0056 (8)	−0.0091 (8)
C16	0.0218 (7)	0.0231 (7)	0.0262 (7)	0.0056 (5)	0.0035 (6)	0.0016 (6)
C6	0.0327 (8)	0.0325 (8)	0.0219 (7)	0.0077 (6)	−0.0047 (6)	0.0053 (6)
C5	0.0386 (9)	0.0352 (8)	0.0305 (8)	0.0084 (7)	−0.0077 (7)	0.0045 (7)
C3	0.0280 (8)	0.0278 (7)	0.0303 (8)	0.0044 (6)	0.0078 (6)	0.0058 (6)
C2	0.0198 (7)	0.0268 (7)	0.0350 (8)	0.0038 (6)	0.0035 (6)	0.0044 (6)
C4	0.0316 (8)	0.0219 (7)	0.0237 (7)	0.0066 (6)	−0.0004 (6)	0.0024 (6)

Geometric parameters (Å, º) top

S1—C1	1.6805 (14)	C8—H8B	0.99
S2—C9	1.6820 (14)	C11—C10	1.333 (2)
N4—C9	1.3576 (18)	C11—H11	0.95
N4—C11	1.3799 (18)	C10—H10	0.95
N4—C14	1.4609 (18)	C15—C16	1.5196 (19)
N3—C9	1.3721 (18)	C15—H15A	0.99
N3—C10	1.3914 (18)	C15—H15B	0.99
N3—C12	1.4078 (18)	C12—C13	1.299 (2)
N2—C1	1.3531 (18)	C12—H12	0.95
N2—C3	1.3812 (18)	C13—H13A	0.95
N2—C6	1.4585 (18)	C13—H13B	0.95
N1—C1	1.3724 (17)	C16—C16ⁱⁱ	1.517 (3)
N1—C2	1.3889 (18)	C16—H16A	0.99
N1—C4	1.4101 (18)	C16—H16B	0.99
C14—C15	1.5188 (19)	C6—H6A	0.99
C14—H14A	0.99	C6—H6B	0.99
C14—H14B	0.99	C5—C4	1.309 (2)
C7—C6	1.514 (2)	C5—H5A	0.95
C7—C8	1.5178 (19)	C5—H5B	0.95
C7—H7A	0.99	C3—C2	1.333 (2)
C7—H7B	0.99	C3—H3	0.95
C8—C8ⁱ	1.521 (3)	C2—H2	0.95
C8—H8A	0.99	C4—H4	0.95

C9—N4—C11	110.30 (12)	C11—C10—N3	107.23 (13)
C9—N4—C14	124.54 (12)	C11—C10—H10	126.4
C11—N4—C14	125.10 (12)	N3—C10—H10	126.4
C9—N3—C10	109.60 (12)	C14—C15—C16	114.16 (12)
C9—N3—C12	123.89 (12)	C14—C15—H15A	108.7
C10—N3—C12	126.51 (12)	C16—C15—H15A	108.7
C1—N2—C3	110.19 (12)	C14—C15—H15B	108.7
C1—N2—C6	124.83 (12)	C16—C15—H15B	108.7
C3—N2—C6	124.68 (12)	H15A—C15—H15B	107.6
C1—N1—C2	109.63 (11)	C13—C12—N3	125.10 (14)
C1—N1—C4	123.53 (12)	C13—C12—H12	117.4
C2—N1—C4	126.82 (12)	N3—C12—H12	117.4
N2—C1—N1	105.20 (11)	C12—C13—H13A	120
N2—C1—S1	127.50 (10)	C12—C13—H13B	120
N1—C1—S1	127.29 (10)	H13A—C13—H13B	120
N4—C14—C15	111.76 (11)	C16ⁱⁱ—C16—C15	112.40 (14)
N4—C14—H14A	109.3	C16ⁱⁱ—C16—H16A	109.1
C15—C14—H14A	109.3	C15—C16—H16A	109.1
N4—C14—H14B	109.3	C16ⁱⁱ—C16—H16B	109.1
C15—C14—H14B	109.3	C15—C16—H16B	109.1
H14A—C14—H14B	107.9	H16A—C16—H16B	107.9
N4—C9—N3	105.07 (12)	N2—C6—C7	111.33 (12)
N4—C9—S2	127.37 (11)	N2—C6—H6A	109.4
N3—C9—S2	127.56 (11)	C7—C6—H6A	109.4
C6—C7—C8	113.07 (12)	N2—C6—H6B	109.4
C6—C7—H7A	109	C7—C6—H6B	109.4
C8—C7—H7A	109	H6A—C6—H6B	108
C6—C7—H7B	109	C4—C5—H5A	120
C8—C7—H7B	109	C4—C5—H5B	120
H7A—C7—H7B	107.8	H5A—C5—H5B	120
C7—C8—C8ⁱ	112.14 (15)	C2—C3—N2	107.85 (13)
C7—C8—H8A	109.2	C2—C3—H3	126.1
C8ⁱ—C8—H8A	109.2	N2—C3—H3	126.1
C7—C8—H8B	109.2	C3—C2—N1	107.13 (12)
C8ⁱ—C8—H8B	109.2	C3—C2—H2	126.4
H8A—C8—H8B	107.9	N1—C2—H2	126.4
C10—C11—N4	107.79 (12)	C5—C4—N1	124.94 (14)
C10—C11—H11	126.1	C5—C4—H4	117.5
N4—C11—H11	126.1	N1—C4—H4	117.5

C3—N2—C1—N1	−0.75 (15)	C9—N4—C11—C10	0.59 (15)
C6—N2—C1—N1	−174.72 (12)	C14—N4—C11—C10	177.66 (12)
C3—N2—C1—S1	178.20 (10)	N4—C11—C10—N3	−0.32 (15)
C6—N2—C1—S1	4.2 (2)	C9—N3—C10—C11	−0.04 (16)
C2—N1—C1—N2	0.35 (14)	C12—N3—C10—C11	178.96 (13)
C4—N1—C1—N2	178.70 (11)	N4—C14—C15—C16	65.34 (16)
C2—N1—C1—S1	−178.60 (10)	C9—N3—C12—C13	173.65 (16)
C4—N1—C1—S1	−0.25 (19)	C10—N3—C12—C13	−5.2 (2)
C9—N4—C14—C15	83.69 (16)	C14—C15—C16—C16ⁱⁱ	179.71 (14)
C11—N4—C14—C15	−92.97 (15)	C1—N2—C6—C7	95.37 (16)
C11—N4—C9—N3	−0.59 (14)	C3—N2—C6—C7	−77.73 (17)
C14—N4—C9—N3	−177.68 (11)	C8—C7—C6—N2	−172.50 (12)
C11—N4—C9—S2	179.67 (10)	C1—N2—C3—C2	0.89 (16)
C14—N4—C9—S2	2.58 (19)	C6—N2—C3—C2	174.87 (13)
C10—N3—C9—N4	0.39 (14)	N2—C3—C2—N1	−0.64 (16)
C12—N3—C9—N4	−178.64 (12)	C1—N1—C2—C3	0.18 (15)
C10—N3—C9—S2	−179.88 (10)	C4—N1—C2—C3	−178.10 (13)
C12—N3—C9—S2	1.09 (19)	C1—N1—C4—C5	−179.54 (14)
C6—C7—C8—C8ⁱ	−179.90 (15)	C2—N1—C4—C5	−1.5 (2)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and N3/N4/C9–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg2ⁱⁱⁱ	0.99	2.75	3.628 (2)	148
C15—H15B···Cg1ⁱⁱ	0.99	2.76	3.589 (2)	142

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

References

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Volume 2| Part 4| April 2017| x170599

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,3′-(Hexane-1,6-di­yl)bis­­(1-vinyl-4-imidazoline-2-thione)

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

3,3′-(Hexane-1,6-diyl)bis(1-vinyl-4-imidazoline-2-thione)