Tris(2-hydroxy-ethyl)ammonium 1,3-benzo-thia-zole-2-thiol-ate.

In the title compound, C(6)H(16)NO(3) (+)·C(7)H(4)NS(2) (-), the cations and anions are connected by O-H⋯N and O-H⋯S hydrogen bonding. Weak C-H⋯O hydrogen bonding between adjacent cations helps to stabilize the crystal structure.

Related literature

For related structures, see Bethge et al. (2008 ▶); Siracusa et al. (2008 ▶); Solar et al. (2008 ▶); Varlamov et al. (2005 ▶).

Experimental

Crystal data

C6H16NO3 +·C7H4NS2 −

M = 316.43

Monoclinic,

a = 16.496 (2) Å

b = 5.7184 (8) Å

c = 17.462 (3) Å

β = 111.524 (2)°

V = 1532.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.56 × 0.38 × 0.23 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.803, T max = 0.921

7572 measured reflections

2827 independent reflections

2185 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.04

2827 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902248X/xu2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902248X/xu2531Isup2.hkl

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

C6H16NO3+·C7H4NS2−	F(000) = 672
Mr = 316.43	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 236 reflections
a = 16.496 (2) Å	θ = 2.4–25.5°
b = 5.7184 (8) Å	µ = 0.36 mm−1
c = 17.462 (3) Å	T = 296 K
β = 111.524 (2)°	Block, colorless
V = 1532.3 (4) Å3	0.56 × 0.38 × 0.23 mm
Z = 4

Bruker SMART area-detector diffractometer	2827 independent reflections
Radiation source: fine-focus sealed tube	2185 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.803, Tmax = 0.921	k = −6→6
7572 measured reflections	l = −20→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.2793P] where P = (Fo2 + 2Fc2)/3
2827 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
C1	0.26675 (13)	1.1324 (4)	0.12815 (11)	0.0361 (5)
C2	0.39268 (13)	0.8624 (4)	0.15930 (11)	0.0347 (5)
C3	0.39516 (12)	1.0658 (3)	0.11586 (11)	0.0347 (5)
C4	0.46629 (14)	1.1048 (4)	0.09259 (13)	0.0459 (5)
H4	0.4692	1.2382	0.0632	0.055*
C5	0.53229 (15)	0.9413 (5)	0.11398 (14)	0.0521 (6)
H5	0.5803	0.9667	0.0992	0.062*
C6	0.52890 (15)	0.7410 (4)	0.15671 (13)	0.0498 (6)
H6	0.5743	0.6335	0.1699	0.060*
C7	0.45902 (14)	0.6983 (4)	0.18000 (12)	0.0445 (5)
H7	0.4565	0.5634	0.2088	0.053*
C8	0.25776 (13)	0.6974 (4)	0.44442 (12)	0.0412 (5)
H8A	0.2820	0.5472	0.4383	0.049*
H8B	0.2541	0.7025	0.4986	0.049*
C9	0.31648 (14)	0.8890 (4)	0.43727 (13)	0.0451 (5)
H9A	0.3726	0.8760	0.4819	0.054*
H9B	0.3257	0.8727	0.3858	0.054*
C10	0.09961 (15)	0.6154 (4)	0.40603 (14)	0.0501 (6)
H10A	0.1175	0.4593	0.4272	0.060*
H10B	0.0458	0.6019	0.3585	0.060*
C11	0.08354 (14)	0.7592 (4)	0.47092 (14)	0.0485 (6)
H11A	0.0323	0.7022	0.4798	0.058*
H11B	0.1330	0.7479	0.5224	0.058*
C12	0.16366 (15)	0.6302 (4)	0.29797 (12)	0.0477 (6)
H12A	0.1524	0.4633	0.2951	0.057*
H12B	0.2190	0.6556	0.2916	0.057*
C13	0.09228 (15)	0.7522 (5)	0.22968 (13)	0.0537 (6)
H13A	0.0969	0.7155	0.1772	0.064*
H13B	0.0359	0.6984	0.2282	0.064*
N1	0.32350 (11)	1.2134 (3)	0.09787 (10)	0.0371 (4)
N2	0.16844 (9)	0.7219 (3)	0.38008 (9)	0.0318 (4)
H2A	0.1569	0.8778	0.3736	0.038*
O1	0.28024 (11)	1.1097 (3)	0.44019 (9)	0.0515 (4)
H1	0.2898	1.1449	0.4882	0.077*
O2	0.07100 (11)	0.9936 (3)	0.44415 (9)	0.0581 (4)
H2	0.0927	1.0808	0.4837	0.087*
O3	0.09930 (10)	0.9968 (3)	0.24292 (9)	0.0533 (4)
H3	0.1244	1.0551	0.2148	0.080*
S1	0.29720 (3)	0.86166 (10)	0.17920 (3)	0.04177 (18)
S2	0.16918 (4)	1.25406 (11)	0.11908 (4)	0.04881 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0443 (12)	0.0320 (12)	0.0297 (10)	−0.0048 (9)	0.0107 (9)	−0.0028 (9)
C2	0.0382 (11)	0.0340 (12)	0.0270 (9)	−0.0052 (9)	0.0063 (8)	−0.0007 (9)
C3	0.0405 (11)	0.0326 (11)	0.0289 (9)	−0.0054 (9)	0.0103 (8)	−0.0021 (9)
C4	0.0496 (13)	0.0463 (15)	0.0453 (12)	−0.0018 (11)	0.0215 (10)	0.0073 (11)
C5	0.0451 (13)	0.0620 (17)	0.0543 (14)	−0.0008 (11)	0.0245 (11)	−0.0012 (12)
C6	0.0465 (13)	0.0513 (16)	0.0478 (13)	0.0115 (11)	0.0128 (11)	−0.0004 (11)
C7	0.0509 (13)	0.0388 (13)	0.0379 (11)	0.0017 (10)	0.0094 (10)	0.0031 (10)
C8	0.0392 (12)	0.0404 (13)	0.0411 (11)	0.0054 (9)	0.0114 (9)	0.0034 (10)
C9	0.0449 (12)	0.0458 (14)	0.0457 (12)	−0.0063 (10)	0.0181 (10)	−0.0091 (11)
C10	0.0506 (13)	0.0500 (15)	0.0526 (13)	−0.0124 (11)	0.0225 (11)	−0.0010 (11)
C11	0.0449 (13)	0.0574 (16)	0.0485 (13)	−0.0021 (11)	0.0234 (11)	0.0049 (12)
C12	0.0649 (15)	0.0422 (14)	0.0375 (11)	0.0001 (11)	0.0204 (11)	−0.0070 (10)
C13	0.0533 (14)	0.0671 (18)	0.0342 (11)	−0.0093 (12)	0.0082 (10)	0.0001 (11)
N1	0.0436 (10)	0.0307 (10)	0.0375 (9)	−0.0019 (8)	0.0154 (8)	0.0030 (7)
N2	0.0351 (9)	0.0275 (9)	0.0319 (8)	0.0001 (7)	0.0110 (7)	0.0011 (7)
O1	0.0690 (10)	0.0380 (10)	0.0454 (8)	−0.0041 (8)	0.0186 (8)	−0.0074 (7)
O2	0.0705 (11)	0.0570 (12)	0.0490 (9)	0.0164 (9)	0.0244 (8)	0.0038 (8)
O3	0.0591 (10)	0.0590 (12)	0.0462 (9)	0.0122 (8)	0.0244 (7)	0.0144 (8)
S1	0.0457 (3)	0.0401 (3)	0.0402 (3)	−0.0032 (2)	0.0166 (2)	0.0092 (2)
S2	0.0518 (4)	0.0470 (4)	0.0536 (4)	0.0074 (3)	0.0263 (3)	0.0074 (3)

C1—N1	1.317 (2)	C9—H9A	0.9700
C1—S2	1.707 (2)	C9—H9B	0.9700
C1—S1	1.765 (2)	C10—N2	1.497 (2)
C2—C7	1.385 (3)	C10—C11	1.500 (3)
C2—C3	1.398 (3)	C10—H10A	0.9700
C2—S1	1.733 (2)	C10—H10B	0.9700
C3—N1	1.391 (2)	C11—O2	1.410 (3)
C3—C4	1.393 (3)	C11—H11A	0.9700
C4—C5	1.379 (3)	C11—H11B	0.9700
C4—H4	0.9300	C12—N2	1.501 (2)
C5—C6	1.379 (3)	C12—C13	1.505 (3)
C5—H5	0.9300	C12—H12A	0.9700
C6—C7	1.378 (3)	C12—H12B	0.9700
C6—H6	0.9300	C13—O3	1.415 (3)
C7—H7	0.9300	C13—H13A	0.9700
C8—N2	1.496 (2)	C13—H13B	0.9700
C8—C9	1.497 (3)	N2—H2A	0.9100
C8—H8A	0.9700	O1—H1	0.8200
C8—H8B	0.9700	O2—H2	0.8200
C9—O1	1.405 (3)	O3—H3	0.8200
N1—C1—S2	127.19 (16)	N2—C10—H10A	109.3
N1—C1—S1	113.51 (15)	C11—C10—H10A	109.3
S2—C1—S1	119.24 (11)	N2—C10—H10B	109.3
C7—C2—C3	121.86 (19)	C11—C10—H10B	109.3
C7—C2—S1	129.44 (16)	H10A—C10—H10B	107.9
C3—C2—S1	108.70 (15)	O2—C11—C10	108.40 (17)
N1—C3—C4	125.02 (18)	O2—C11—H11A	110.0
N1—C3—C2	115.84 (17)	C10—C11—H11A	110.0
C4—C3—C2	119.13 (19)	O2—C11—H11B	110.0
C5—C4—C3	118.6 (2)	C10—C11—H11B	110.0
C5—C4—H4	120.7	H11A—C11—H11B	108.4
C3—C4—H4	120.7	N2—C12—C13	110.28 (18)
C4—C5—C6	121.7 (2)	N2—C12—H12A	109.6
C4—C5—H5	119.2	C13—C12—H12A	109.6
C6—C5—H5	119.2	N2—C12—H12B	109.6
C7—C6—C5	120.7 (2)	C13—C12—H12B	109.6
C7—C6—H6	119.6	H12A—C12—H12B	108.1
C5—C6—H6	119.6	O3—C13—C12	109.59 (18)
C6—C7—C2	118.0 (2)	O3—C13—H13A	109.8
C6—C7—H7	121.0	C12—C13—H13A	109.8
C2—C7—H7	121.0	O3—C13—H13B	109.8
N2—C8—C9	110.98 (17)	C12—C13—H13B	109.8
N2—C8—H8A	109.4	H13A—C13—H13B	108.2
C9—C8—H8A	109.4	C1—N1—C3	111.49 (17)
N2—C8—H8B	109.4	C8—N2—C10	112.46 (15)
C9—C8—H8B	109.4	C8—N2—C12	112.13 (15)
H8A—C8—H8B	108.0	C10—N2—C12	111.54 (16)
O1—C9—C8	110.92 (17)	C8—N2—H2A	106.8
O1—C9—H9A	109.5	C10—N2—H2A	106.8
C8—C9—H9A	109.5	C12—N2—H2A	106.8
O1—C9—H9B	109.5	C9—O1—H1	109.5
C8—C9—H9B	109.5	C11—O2—H2	109.5
H9A—C9—H9B	108.0	C13—O3—H3	109.5
N2—C10—C11	111.68 (18)	C2—S1—C1	90.44 (9)
C7—C2—C3—N1	178.88 (18)	S2—C1—N1—C3	−178.71 (15)
S1—C2—C3—N1	−1.0 (2)	S1—C1—N1—C3	−1.5 (2)
C7—C2—C3—C4	0.1 (3)	C4—C3—N1—C1	−179.62 (19)
S1—C2—C3—C4	−179.79 (15)	C2—C3—N1—C1	1.7 (2)
N1—C3—C4—C5	−179.2 (2)	C9—C8—N2—C10	−153.34 (17)
C2—C3—C4—C5	−0.5 (3)	C9—C8—N2—C12	80.0 (2)
C3—C4—C5—C6	0.7 (3)	C11—C10—N2—C8	72.5 (2)
C4—C5—C6—C7	−0.4 (3)	C11—C10—N2—C12	−160.57 (18)
C5—C6—C7—C2	−0.1 (3)	C13—C12—N2—C8	−153.34 (18)
C3—C2—C7—C6	0.2 (3)	C13—C12—N2—C10	79.5 (2)
S1—C2—C7—C6	−179.94 (16)	C7—C2—S1—C1	−179.76 (19)
N2—C8—C9—O1	55.1 (2)	C3—C2—S1—C1	0.09 (14)
N2—C10—C11—O2	49.9 (2)	N1—C1—S1—C2	0.85 (15)
N2—C12—C13—O3	48.2 (2)	S2—C1—S1—C2	178.27 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.96	2.770 (2)	168
O2—H2···S2i	0.82	2.43	3.2258 (17)	165
O3—H3···S2	0.82	2.35	3.1621 (16)	169
C8—H8A···O1ii	0.97	2.50	3.385 (3)	151
C10—H10B···O3iii	0.97	2.47	3.425 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.96	2.770 (2)	168
O2—H2⋯S2i	0.82	2.43	3.2258 (17)	165
O3—H3⋯S2	0.82	2.35	3.1621 (16)	169
C8—H8A⋯O1ii	0.97	2.50	3.385 (3)	151
C10—H10B⋯O3iii	0.97	2.47	3.425 (3)	167

Symmetry codes: (i) ; (ii) ; (iii) .