Tripropyl­ammonium trithio­cyanurate

Yang, Y.

doi:10.1107/S1600536810038924

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2793

https://doi.org/10.1107/S1600536810038924

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Tripropylammonium trithiocyanurate

Yunxia Yang ^a ^*

^aKey Laboratory of Eco-environment-related Polymer Materials, Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, Gansu, People's Republic of China
^*Correspondence e-mail: yangyx80@nwnu.edu.cn

(Received 20 September 2010; accepted 29 September 2010; online 13 October 2010)

In the title compound (systematic name: tripropylazanium 2,4,6-trisulfanylidenecyclohexan-1-ide), (C₃H₇)₃HN⁺·C₃H₂N₃S₃⁻, one H atom of trithiocyanuric acid is accepted by tripropylamine to form the ammonium ion. Coplanar trithiocyanurate and tripropylammonium ions [dihedral angle = 82.33 (8)°] form the salt, which is stabilised by various N—H⋯S and N—H⋯N contacts.

Related literature

For the crystal structures of tetraphenylphosphonium salts of trithiocyanuric acid, see: Dean et al. (2004 ).

Experimental

Crystal data

C₉H₂₂N⁺·C₃H₂N₃S₃⁻
M_r = 320.53
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.3677 (5) Å
b = 12.8827 (8) Å
c = 16.5339 (10) Å
V = 1782.33 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 296 K
0.61 × 0.27 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.788, T_max = 0.919
5690 measured reflections
3675 independent reflections
3232 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.097
S = 1.03
3675 reflections
181 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 1316 Friedel pairs
Flack parameter: −0.04 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N3	0.93 (1)	1.95 (1)	2.867 (2)	172 (3)
N1—H1⋯S2ⁱ	0.92 (1)	2.51 (1)	3.4037 (17)	167 (2)
N2—H2⋯S1ⁱⁱ	0.91 (1)	2.39 (1)	3.2911 (17)	170 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810038924/rn2070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038924/rn2070Isup2.hkl

checkCIF report

Comment top

Trithiocyanuric acid, which can be regarded as the polymer of three thiourea molecules, tends to form various hydrogen bonds with its hydrogen-bond donor and acceptor (Dean et al. 2004). Here we reported the cocrystal of the tripropylammonium cation and trithiocyanurate with a molar ratio of 1:1, (C₃H₇)₃HN⁺.C₃H₂N₃S₃^-. In this structure, the independent planar trithiocyanurate anion only form a pair of N—H···S hydrogen bonds, of which N···S distances are 3.404 (2) Å and 3.291 (2) Å and the corresponding angles 166.6° and 169.7°, to generate the hydrogen-bonded ribbons along the b axis, and these ribbons which are translated by 2₁ rotation axis are orderly arranged almost along the (101) and (101)directions. Subsequently, the central N—H group of the ammonium cation can form an N—H···N donor hydrogen bond (N···N distance is 2.867 (2) Å and the related angle is 172.5°) with one of the nitrogen atom located in the trithiocyanurate to generate the final stable cocrystal.

Related literature top

For the crystal structures of tetraphenylphosphonium salts of trithiocyanuric acid, see: Dean et al. (2004).

Experimental top

Trithiocyanuric acid (0.044 g, 0.25 mmol) was dissolved in a water-ethanol (1:2 v/v) mixture and tripropylamine was added to neutralize the acid. Colorless block crystals formed after several weeks.

Structure description top

For the crystal structures of tetraphenylphosphonium salts of trithiocyanuric acid, see: Dean et al. (2004).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at the 30% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen bond pattern in the crystal structure of the title compound; all hydrogen atoms bonded to carbon and carbon atoms of the tripropylammonium cation are omitted for clarity and the cations are represented with the hatched spheres.

Tripropylazanium 2,4,6-trisulfanylidenecyclohexan-1-ide top

Crystal data top

C₉H₂₂N⁺·C₃H₂N₃S₃⁻	F(000) = 688
M_r = 320.53	D_x = 1.195 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.3677 (5) Å	µ = 0.41 mm⁻¹
b = 12.8827 (8) Å	T = 296 K
c = 16.5339 (10) Å	Block, colorless
V = 1782.33 (19) Å³	0.61 × 0.27 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3675 independent reflections
Radiation source: fine-focus sealed tube	3232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
phi and ω scans	θ_max = 27.6°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→10
T_min = 0.788, T_max = 0.919	k = −16→16
5690 measured reflections	l = −17→19

Refinement top

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.057P)² + 0.1498P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3675 reflections	Δρ_max = 0.24 e Å⁻³
181 parameters	Δρ_min = −0.20 e Å⁻³
3 restraints	Absolute structure: Flack & Bernardinelli (2000), 1316 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (8)

Crystal data top

C₉H₂₂N⁺·C₃H₂N₃S₃⁻	V = 1782.33 (19) Å³
M_r = 320.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.3677 (5) Å	µ = 0.41 mm⁻¹
b = 12.8827 (8) Å	T = 296 K
c = 16.5339 (10) Å	0.61 × 0.27 × 0.21 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3675 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3232 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.919	R_int = 0.013
5690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	Δρ_max = 0.24 e Å⁻³
S = 1.03	Δρ_min = −0.20 e Å⁻³
3675 reflections	Absolute structure: Flack & Bernardinelli (2000), 1316 Friedel pairs
181 parameters	Absolute structure parameter: −0.04 (8)
3 restraints

Special details top

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
N4	0.25770 (18)	0.02494 (16)	0.48456 (11)	0.0513 (4)
H4	0.307 (3)	0.020 (2)	0.5345 (9)	0.077*
C4	0.3656 (3)	0.0945 (2)	0.43528 (14)	0.0603 (6)
H4A	0.3771	0.1602	0.4634	0.072*
H4B	0.4706	0.0629	0.4324	0.072*
C5	0.3087 (3)	0.1159 (2)	0.35052 (17)	0.0726 (7)
H5A	0.2116	0.1570	0.3525	0.087*
H5B	0.2843	0.0509	0.3237	0.087*
C7	0.2386 (3)	−0.0818 (2)	0.44928 (15)	0.0596 (5)
H7A	0.1680	−0.0775	0.4029	0.072*
H7B	0.1872	−0.1259	0.4891	0.072*
C8	0.3920 (3)	−0.1327 (2)	0.42319 (19)	0.0756 (7)
H8A	0.4343	−0.0967	0.3763	0.091*
H8B	0.4700	−0.1275	0.4664	0.091*
C9	0.3658 (6)	−0.2448 (3)	0.4026 (3)	0.1228 (14)
H9A	0.4652	−0.2754	0.3862	0.184*
H9B	0.2899	−0.2500	0.3593	0.184*
H9C	0.3255	−0.2807	0.4492	0.184*
C10	0.0991 (2)	0.0762 (2)	0.50164 (16)	0.0605 (5)
H10A	0.1181	0.1469	0.5194	0.073*
H10B	0.0380	0.0794	0.4518	0.073*
C11	0.0026 (4)	0.0216 (3)	0.5642 (2)	0.0995 (11)
H11A	−0.0111	−0.0501	0.5476	0.119*
H11B	0.0620	0.0215	0.6145	0.119*
C12	−0.1564 (4)	0.0668 (4)	0.5792 (3)	0.1253 (15)
H12A	−0.2104	0.0272	0.6201	0.188*
H12B	−0.2178	0.0655	0.5302	0.188*
H12C	−0.1446	0.1373	0.5972	0.188*
C6	0.4346 (4)	0.1736 (3)	0.3029 (2)	0.1079 (12)
H6A	0.3962	0.1865	0.2492	0.162*
H6B	0.5302	0.1325	0.3003	0.162*
H6C	0.4576	0.2385	0.3291	0.162*
N1	0.5530 (2)	−0.05504 (13)	0.74298 (10)	0.0468 (4)
H1	0.579 (3)	−0.1170 (12)	0.7667 (15)	0.070*
N2	0.5353 (2)	0.12080 (13)	0.74422 (11)	0.0456 (4)
H2	0.556 (3)	0.1813 (12)	0.7704 (14)	0.068*
N3	0.40788 (18)	0.02890 (11)	0.64040 (10)	0.0449 (3)
S1	0.40179 (9)	−0.17606 (4)	0.63935 (4)	0.06707 (19)
C1	0.4565 (2)	−0.05976 (15)	0.67496 (12)	0.0451 (4)
S2	0.37526 (8)	0.23360 (4)	0.63897 (4)	0.06029 (17)
C2	0.5970 (2)	0.03521 (15)	0.77943 (11)	0.0433 (4)
S3	0.71163 (7)	0.03940 (5)	0.86074 (4)	0.06204 (17)
C3	0.4425 (2)	0.12015 (15)	0.67552 (13)	0.0433 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0444 (8)	0.0640 (11)	0.0455 (10)	−0.0042 (8)	−0.0042 (7)	0.0042 (9)
C4	0.0544 (12)	0.0713 (15)	0.0551 (14)	−0.0120 (11)	−0.0025 (10)	0.0083 (11)
C5	0.0656 (15)	0.0872 (18)	0.0652 (17)	−0.0049 (12)	−0.0052 (13)	0.0186 (14)
C7	0.0542 (12)	0.0604 (14)	0.0644 (14)	−0.0008 (10)	−0.0020 (10)	0.0050 (12)
C8	0.0701 (16)	0.0829 (19)	0.0738 (18)	0.0131 (14)	0.0119 (14)	0.0102 (14)
C9	0.135 (3)	0.081 (2)	0.153 (4)	0.027 (2)	0.041 (3)	−0.012 (2)
C10	0.0527 (11)	0.0668 (14)	0.0620 (14)	0.0011 (11)	0.0006 (10)	−0.0056 (12)
C11	0.0817 (19)	0.111 (3)	0.106 (2)	0.0086 (19)	0.0401 (18)	0.022 (2)
C12	0.090 (2)	0.151 (4)	0.135 (3)	0.003 (2)	0.051 (2)	−0.023 (3)
C6	0.101 (2)	0.139 (3)	0.085 (2)	−0.013 (2)	0.012 (2)	0.042 (2)
N1	0.0544 (9)	0.0391 (9)	0.0470 (10)	0.0028 (7)	−0.0065 (7)	0.0042 (7)
N2	0.0514 (9)	0.0403 (9)	0.0452 (10)	−0.0020 (7)	−0.0070 (7)	−0.0003 (7)
N3	0.0556 (8)	0.0365 (7)	0.0425 (8)	−0.0003 (7)	−0.0068 (7)	0.0030 (8)
S1	0.1045 (5)	0.0372 (3)	0.0596 (4)	−0.0009 (3)	−0.0251 (4)	−0.0006 (3)
C1	0.0522 (10)	0.0395 (10)	0.0435 (11)	0.0010 (8)	−0.0003 (8)	0.0020 (8)
S2	0.0818 (4)	0.0363 (2)	0.0627 (4)	0.0006 (2)	−0.0236 (3)	0.0047 (2)
C2	0.0377 (8)	0.0468 (10)	0.0454 (11)	−0.0006 (8)	0.0006 (7)	0.0032 (9)
S3	0.0603 (3)	0.0634 (3)	0.0624 (4)	0.0002 (3)	−0.0234 (3)	0.0022 (3)
C3	0.0455 (10)	0.0404 (9)	0.0441 (11)	−0.0015 (7)	−0.0009 (9)	0.0029 (8)

Geometric parameters (Å, º) top

N4—C7	1.503 (3)	C10—H10B	0.9700
N4—C10	1.509 (3)	C11—C12	1.474 (5)
N4—C4	1.511 (3)	C11—H11A	0.9700
N4—H4	0.925 (10)	C11—H11B	0.9700
C4—C5	1.506 (4)	C12—H12A	0.9600
C4—H4A	0.9700	C12—H12B	0.9600
C4—H4B	0.9700	C12—H12C	0.9600
C5—C6	1.510 (4)	C6—H6A	0.9600
C5—H5A	0.9700	C6—H6B	0.9600
C5—H5B	0.9700	C6—H6C	0.9600
C7—C8	1.504 (3)	N1—C2	1.360 (3)
C7—H7A	0.9700	N1—C1	1.386 (3)
C7—H7B	0.9700	N1—H1	0.915 (10)
C8—C9	1.499 (5)	N2—C2	1.350 (2)
C8—H8A	0.9700	N2—C3	1.376 (3)
C8—H8B	0.9700	N2—H2	0.908 (10)
C9—H9A	0.9600	N3—C1	1.341 (2)
C9—H9B	0.9600	N3—C3	1.343 (2)
C9—H9C	0.9600	S1—C1	1.674 (2)
C10—C11	1.489 (4)	S2—C3	1.679 (2)
C10—H10A	0.9700	C2—S3	1.6525 (19)

C7—N4—C10	112.32 (16)	N4—C10—H10A	108.9
C7—N4—C4	113.42 (18)	C11—C10—H10B	108.9
C10—N4—C4	111.51 (19)	N4—C10—H10B	108.9
C7—N4—H4	109.2 (19)	H10A—C10—H10B	107.7
C10—N4—H4	104.8 (17)	C12—C11—C10	114.8 (3)
C4—N4—H4	104.9 (17)	C12—C11—H11A	108.6
C5—C4—N4	114.92 (18)	C10—C11—H11A	108.6
C5—C4—H4A	108.5	C12—C11—H11B	108.6
N4—C4—H4A	108.5	C10—C11—H11B	108.6
C5—C4—H4B	108.5	H11A—C11—H11B	107.5
N4—C4—H4B	108.5	C11—C12—H12A	109.5
H4A—C4—H4B	107.5	C11—C12—H12B	109.5
C4—C5—C6	110.7 (2)	H12A—C12—H12B	109.5
C4—C5—H5A	109.5	C11—C12—H12C	109.5
C6—C5—H5A	109.5	H12A—C12—H12C	109.5
C4—C5—H5B	109.5	H12B—C12—H12C	109.5
C6—C5—H5B	109.5	C5—C6—H6A	109.5
H5A—C5—H5B	108.1	C5—C6—H6B	109.5
N4—C7—C8	114.8 (2)	H6A—C6—H6B	109.5
N4—C7—H7A	108.6	C5—C6—H6C	109.5
C8—C7—H7A	108.6	H6A—C6—H6C	109.5
N4—C7—H7B	108.6	H6B—C6—H6C	109.5
C8—C7—H7B	108.6	C2—N1—C1	123.70 (17)
H7A—C7—H7B	107.5	C2—N1—H1	119.4 (17)
C9—C8—C7	111.1 (3)	C1—N1—H1	116.6 (17)
C9—C8—H8A	109.4	C2—N2—C3	124.54 (17)
C7—C8—H8A	109.4	C2—N2—H2	115.0 (17)
C9—C8—H8B	109.4	C3—N2—H2	120.4 (17)
C7—C8—H8B	109.4	C1—N3—C3	119.75 (16)
H8A—C8—H8B	108.0	N3—C1—N1	119.04 (17)
C8—C9—H9A	109.5	N3—C1—S1	121.99 (15)
C8—C9—H9B	109.5	N1—C1—S1	118.96 (15)
H9A—C9—H9B	109.5	N2—C2—N1	113.81 (16)
C8—C9—H9C	109.5	N2—C2—S3	123.12 (15)
H9A—C9—H9C	109.5	N1—C2—S3	123.06 (15)
H9B—C9—H9C	109.5	N3—C3—N2	118.95 (17)
C11—C10—N4	113.6 (2)	N3—C3—S2	122.30 (15)
C11—C10—H10A	108.9	N2—C3—S2	118.75 (15)

C7—N4—C4—C5	61.7 (3)	C2—N1—C1—N3	2.8 (3)
C10—N4—C4—C5	−66.3 (3)	C2—N1—C1—S1	−176.22 (15)
N4—C4—C5—C6	−172.3 (3)	C3—N2—C2—N1	−3.0 (3)
C10—N4—C7—C8	174.1 (2)	C3—N2—C2—S3	178.48 (15)
C4—N4—C7—C8	46.6 (3)	C1—N1—C2—N2	1.3 (3)
N4—C7—C8—C9	170.0 (3)	C1—N1—C2—S3	179.77 (16)
C7—N4—C10—C11	63.9 (3)	C1—N3—C3—N2	3.6 (3)
C4—N4—C10—C11	−167.5 (2)	C1—N3—C3—S2	−175.92 (16)
N4—C10—C11—C12	−177.1 (3)	C2—N2—C3—N3	0.7 (3)
C3—N3—C1—N1	−5.2 (3)	C2—N2—C3—S2	−179.76 (16)
C3—N3—C1—S1	173.75 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3	0.93 (1)	1.95 (1)	2.867 (2)	172 (3)
N1—H1···S2ⁱ	0.92 (1)	2.51 (1)	3.4037 (17)	167 (2)
N2—H2···S1ⁱⁱ	0.91 (1)	2.39 (1)	3.2911 (17)	170 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₉H₂₂N⁺·C₃H₂N₃S₃⁻
M_r	320.53
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.3677 (5), 12.8827 (8), 16.5339 (10)
V (Å³)	1782.33 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.61 × 0.27 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.788, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	5690, 3675, 3232
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.03
No. of reflections	3675
No. of parameters	181
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20
Absolute structure	Flack & Bernardinelli (2000), 1316 Friedel pairs
Absolute structure parameter	−0.04 (8)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3	0.925 (10)	1.947 (11)	2.867 (2)	172 (3)
N1—H1···S2ⁱ	0.915 (10)	2.507 (12)	3.4037 (17)	167 (2)
N2—H2···S1ⁱⁱ	0.908 (10)	2.393 (11)	3.2911 (17)	170 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2.

Acknowledgements

The author thanks the Key Laboratory of Eco-environment-related Polymer Materials of Northwest Normal University for supporting this work.

References

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