2-Anilino-3-(2-hy-droxy-prop-yl)-4-methyl-1,3-thia-zol-3-ium chloride.

In the title compound, C(13)H(17)N(2)OS(+)·Cl(-), the thia-zolium ring mean plane makes a dihedral angle of 55.46 (9)° with the benzene ring. In the propanol group, the N-C-C-C and N-C-C-O torsion angles are 172.58 (15) and 52.9 (2)°, respectively, and the S-C-C-C torsion angle is 178.99 (18)°. In the crystal, mol-ecules are linked by O-H⋯Cl and N-H⋯Cl hydrogen bonds, forming zigzag chains along [001]. There is also a C-H⋯Cl inter-action present.

Related literature

The title compound was prepared as part of an ongoing investigation into the synthesis and biological properties of thia­zole compounds: see; Abdel-Wahab et al. (2009 ▶); Baia et al. (2008 ▶); Lesyk et al. (2007 ▶); Mohamed et al. (2012a ▶,b ▶); Potikha et al. (2008 ▶); Shiradkar et al. (2007 ▶); Soliman et al. (2012 ▶); Wu & Yang (2007 ▶). For related structures, see: Lynch & McClenaghan (2004 ▶); Liu et al. (2011 ▶); Wang (2011 ▶).

Experimental

Crystal data

C13H17N2OS+·Cl−

M = 284.81

Monoclinic,

a = 11.7570 (4) Å

b = 12.2477 (4) Å

c = 10.2954 (3) Å

β = 106.532 (1)°

V = 1421.21 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 K

0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.898, T max = 0.922

10535 measured reflections

2641 independent reflections

2172 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.03

2641 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023197/su2431sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023197/su2431Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023197/su2431Isup3.cml

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

C13H17N2OS+·Cl−	F(000) = 600
Mr = 284.81	Dx = 1.331 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 447 reflections
a = 11.7570 (4) Å	θ = 3.5–21.2°
b = 12.2477 (4) Å	µ = 0.41 mm−1
c = 10.2954 (3) Å	T = 296 K
β = 106.532 (1)°	Rod, colourless
V = 1421.21 (8) Å3	0.35 × 0.22 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2641 independent reflections
Radiation source: fine-focus sealed tube	2172 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 0.81 pixels mm-1	θmax = 25.5°, θmin = 2.5°
ω scans	h = −14→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.898, Tmax = 0.922	l = −12→12
10535 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3249P] where P = (Fo2 + 2Fc2)/3
2641 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	0.53335 (4)	0.36209 (4)	−0.02819 (4)	0.0436 (2)
O1	0.92376 (12)	0.25939 (14)	0.20894 (15)	0.0722 (6)
N1	0.58597 (12)	0.35477 (12)	0.24335 (13)	0.0424 (4)
N2	0.73113 (12)	0.41117 (12)	0.13880 (14)	0.0447 (5)
C1	0.47013 (14)	0.31414 (14)	0.23234 (15)	0.0382 (5)
C2	0.40120 (15)	0.36823 (15)	0.30052 (17)	0.0455 (6)
C3	0.29021 (17)	0.3281 (2)	0.29410 (19)	0.0586 (7)
C4	0.24821 (17)	0.2359 (2)	0.22085 (19)	0.0673 (8)
C5	0.31707 (18)	0.18174 (19)	0.15336 (18)	0.0612 (7)
C6	0.42873 (16)	0.22021 (15)	0.15893 (16)	0.0471 (6)
C7	0.62227 (15)	0.37561 (13)	0.13445 (16)	0.0384 (5)
C8	0.74511 (17)	0.42898 (16)	0.00903 (19)	0.0522 (7)
C9	0.64774 (18)	0.40625 (15)	−0.08878 (19)	0.0527 (7)
C10	0.8594 (2)	0.4705 (2)	−0.0071 (2)	0.0812 (9)
C11	0.82819 (15)	0.41979 (16)	0.26481 (18)	0.0509 (6)
C12	0.88729 (16)	0.31168 (18)	0.31206 (19)	0.0544 (7)
C13	0.99588 (18)	0.3309 (2)	0.4314 (2)	0.0775 (9)
Cl1	0.71127 (4)	0.10568 (4)	0.05541 (4)	0.0553 (2)
H1	0.63390	0.36620	0.32250	0.0510*
H1A	0.86790	0.22510	0.16010	0.1080*
H2	0.42940	0.43100	0.35010	0.0550*
H3	0.24340	0.36390	0.33990	0.0700*
H4	0.17300	0.20970	0.21670	0.0810*
H5	0.28820	0.11910	0.10390	0.0730*
H6	0.47560	0.18360	0.11400	0.0560*
H9	0.64160	0.41330	−0.18050	0.0630*
H10A	0.85460	0.47390	−0.10170	0.1220*
H10B	0.92260	0.42230	0.03820	0.1220*
H10C	0.87460	0.54220	0.03170	0.1220*
H11A	0.79720	0.44960	0.33520	0.0610*
H11B	0.88720	0.47040	0.25100	0.0610*
H12	0.83160	0.26440	0.34050	0.0650*
H13A	1.05130	0.37610	0.40350	0.1160*
H13B	1.03240	0.26220	0.46350	0.1160*
H13C	0.97260	0.36660	0.50290	0.1160*

	U11	U22	U33	U12	U13	U23
S1	0.0486 (3)	0.0486 (3)	0.0332 (2)	−0.0003 (2)	0.0112 (2)	0.0015 (2)
O1	0.0544 (8)	0.0909 (12)	0.0737 (10)	0.0018 (8)	0.0221 (8)	−0.0187 (8)
N1	0.0389 (7)	0.0577 (9)	0.0305 (7)	−0.0068 (7)	0.0095 (6)	−0.0046 (6)
N2	0.0429 (8)	0.0501 (9)	0.0424 (8)	−0.0073 (7)	0.0145 (6)	0.0013 (6)
C1	0.0368 (9)	0.0496 (10)	0.0277 (8)	−0.0008 (8)	0.0083 (7)	0.0037 (7)
C2	0.0466 (10)	0.0562 (11)	0.0339 (9)	0.0062 (8)	0.0120 (8)	0.0041 (8)
C3	0.0417 (10)	0.0936 (16)	0.0433 (11)	0.0091 (11)	0.0167 (9)	0.0074 (10)
C4	0.0415 (11)	0.1137 (19)	0.0455 (11)	−0.0179 (12)	0.0106 (9)	0.0083 (12)
C5	0.0641 (13)	0.0781 (15)	0.0387 (10)	−0.0288 (11)	0.0103 (9)	−0.0025 (9)
C6	0.0539 (11)	0.0570 (11)	0.0318 (9)	−0.0069 (9)	0.0146 (8)	−0.0020 (8)
C7	0.0415 (9)	0.0381 (9)	0.0364 (9)	−0.0001 (7)	0.0123 (7)	−0.0007 (7)
C8	0.0578 (11)	0.0555 (12)	0.0491 (11)	−0.0065 (9)	0.0245 (10)	0.0092 (9)
C9	0.0665 (12)	0.0551 (12)	0.0417 (10)	−0.0017 (9)	0.0239 (10)	0.0093 (8)
C10	0.0748 (15)	0.1027 (19)	0.0776 (15)	−0.0227 (14)	0.0402 (13)	0.0156 (14)
C11	0.0423 (10)	0.0619 (12)	0.0494 (11)	−0.0140 (9)	0.0144 (8)	−0.0084 (9)
C12	0.0401 (10)	0.0747 (14)	0.0485 (11)	−0.0024 (9)	0.0127 (8)	−0.0044 (9)
C13	0.0479 (12)	0.117 (2)	0.0612 (13)	−0.0011 (13)	0.0050 (10)	−0.0043 (13)
Cl1	0.0614 (3)	0.0629 (3)	0.0409 (3)	0.0018 (2)	0.0135 (2)	0.0051 (2)

S1—C7	1.7111 (17)	C11—C12	1.510 (3)
S1—C9	1.723 (2)	C12—C13	1.517 (3)
O1—C12	1.407 (2)	C2—H2	0.9300
O1—H1A	0.8200	C3—H3	0.9300
N1—C7	1.333 (2)	C4—H4	0.9300
N1—C1	1.424 (2)	C5—H5	0.9300
N2—C8	1.409 (2)	C6—H6	0.9300
N2—C11	1.468 (2)	C9—H9	0.9300
N2—C7	1.341 (2)	C10—H10A	0.9600
N1—H1	0.8600	C10—H10B	0.9600
C1—C2	1.383 (2)	C10—H10C	0.9600
C1—C6	1.387 (2)	C11—H11A	0.9700
C2—C3	1.378 (3)	C11—H11B	0.9700
C3—C4	1.370 (3)	C12—H12	0.9800
C4—C5	1.378 (3)	C13—H13A	0.9600
C5—C6	1.381 (3)	C13—H13B	0.9600
C8—C9	1.321 (3)	C13—H13C	0.9600
C8—C10	1.490 (3)
C7—S1—C9	90.08 (9)	C4—C3—H3	120.00
C12—O1—H1A	109.00	C3—C4—H4	120.00
C1—N1—C7	121.86 (14)	C5—C4—H4	120.00
C7—N2—C11	123.21 (14)	C4—C5—H5	120.00
C8—N2—C11	123.78 (15)	C6—C5—H5	120.00
C7—N2—C8	112.74 (14)	C1—C6—H6	120.00
C7—N1—H1	119.00	C5—C6—H6	120.00
C1—N1—H1	119.00	S1—C9—H9	124.00
N1—C1—C2	118.53 (15)	C8—C9—H9	124.00
N1—C1—C6	120.85 (15)	C8—C10—H10A	109.00
C2—C1—C6	120.58 (16)	C8—C10—H10B	110.00
C1—C2—C3	119.24 (17)	C8—C10—H10C	109.00
C2—C3—C4	120.57 (19)	H10A—C10—H10B	109.00
C3—C4—C5	120.2 (2)	H10A—C10—H10C	109.00
C4—C5—C6	120.2 (2)	H10B—C10—H10C	109.00
C1—C6—C5	119.21 (17)	N2—C11—H11A	109.00
S1—C7—N1	123.50 (14)	N2—C11—H11B	109.00
S1—C7—N2	112.07 (12)	C12—C11—H11A	109.00
N1—C7—N2	124.42 (15)	C12—C11—H11B	109.00
N2—C8—C9	112.37 (18)	H11A—C11—H11B	108.00
N2—C8—C10	120.73 (16)	O1—C12—H12	109.00
C9—C8—C10	126.90 (18)	C11—C12—H12	109.00
S1—C9—C8	112.74 (15)	C13—C12—H12	109.00
N2—C11—C12	113.11 (15)	C12—C13—H13A	109.00
O1—C12—C11	111.54 (16)	C12—C13—H13B	109.00
O1—C12—C13	108.34 (16)	C12—C13—H13C	109.00
C11—C12—C13	109.20 (18)	H13A—C13—H13B	109.00
C1—C2—H2	120.00	H13A—C13—H13C	109.00
C3—C2—H2	120.00	H13B—C13—H13C	109.00
C2—C3—H3	120.00
C9—S1—C7—N1	178.77 (15)	C8—N2—C7—N1	−178.65 (16)
C9—S1—C7—N2	−0.17 (14)	C8—N2—C11—C12	−94.2 (2)
C7—S1—C9—C8	0.00 (17)	N1—C1—C2—C3	−178.13 (16)
C7—N1—C1—C2	−127.80 (17)	C2—C1—C6—C5	0.7 (3)
C7—N1—C1—C6	54.5 (2)	N1—C1—C6—C5	178.37 (16)
C1—N1—C7—S1	3.0 (2)	C6—C1—C2—C3	−0.4 (3)
C1—N1—C7—N2	−178.18 (16)	C1—C2—C3—C4	−0.2 (3)
C8—N2—C7—S1	0.27 (19)	C2—C3—C4—C5	0.4 (3)
C11—N2—C7—S1	−173.96 (13)	C3—C4—C5—C6	−0.1 (3)
C11—N2—C7—N1	7.1 (3)	C4—C5—C6—C1	−0.4 (3)
C7—N2—C8—C9	−0.3 (2)	N2—C8—C9—S1	0.1 (2)
C11—N2—C8—C9	173.93 (17)	C10—C8—C9—S1	−178.99 (18)
C7—N2—C8—C10	178.92 (18)	N2—C11—C12—O1	52.9 (2)
C11—N2—C8—C10	−6.9 (3)	N2—C11—C12—C13	172.58 (15)
C7—N2—C11—C12	79.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1	0.82	2.36	3.1681 (16)	169
N1—H1···Cl1i	0.86	2.34	3.1675 (14)	163
C11—H11A···Cl1i	0.97	2.81	3.6440 (19)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1	0.82	2.36	3.1681 (16)	169
N1—H1⋯Cl1i	0.86	2.34	3.1675 (14)	163
C11—H11A⋯Cl1i	0.97	2.81	3.6440 (19)	144

Symmetry code: (i) .