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The structure of the title compound, C12H15ClN2OS, (I), comprises a twisted thia­zolium base that associates to a free Cl ion via N—H...Cl hydrogen-bonding interactions. The dihedral angle between the two ring systems is 79.65 (7)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800017876/ob6000sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800017876/ob6000Isup2.hkl
Contains datablock I

CCDC reference: 155863

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.136
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

NO COMMENT

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from a dimethylformamide -solution.

Refinement top

All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H), 0.98 (CH3) and 0.99 Å (CH2), except for the H atoms involved in the hydrogen-bonding interactions which were located on difference syntheses and both positional and displacement parameters refined.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZOand COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2-Amino-5-(4-methoxybenzyl)-4-methyl-1,3-thiazolium chloride top
Crystal data top
C12H15ClN2OSDx = 1.400 Mg m3
Mr = 270.77Melting point: 489 - 493 K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.5746 (15) ÅCell parameters from 10172 reflections
b = 11.878 (2) Åθ = 1.0–27.5°
c = 14.519 (3) ŵ = 0.45 mm1
β = 100.47 (3)°T = 150 K
V = 1284.6 (4) Å3Needle, colourless
Z = 40.20 × 0.08 × 0.06 mm
F(000) = 568
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
2796 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2125 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.2°
ϕ and ω scansh = 99
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1415
Tmin = 0.916, Tmax = 0.974l = 1818
6971 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0691P)2 + 0.162P]
where P = (Fo2 + 2Fc2)/3
2796 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
C12H15ClN2OSV = 1284.6 (4) Å3
Mr = 270.77Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5746 (15) ŵ = 0.45 mm1
b = 11.878 (2) ÅT = 150 K
c = 14.519 (3) Å0.20 × 0.08 × 0.06 mm
β = 100.47 (3)°
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
2796 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
2125 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.974Rint = 0.073
6971 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.40 e Å3
2796 reflectionsΔρmin = 0.55 e Å3
168 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 0.9154 (0.0059) x - 9.5063 (0.0092) y + 8.7040 (0.0135) z = 5.1034 (0.0111)

* 0.0004 (0.0010) S1 * -0.0017 (0.0012) C2 * 0.0026 (0.0014) N3 * -0.0022 (0.0015) C4 * 0.0010 (0.0014) C5

Rms deviation of fitted atoms = 0.0018

- 1.0226 (0.0075) x + 8.7142 (0.0091) y + 9.8653 (0.0116) z = 11.4669 (0.0109)

Angle to previous plane (with approximate e.s.d.) = 79.65 (0.07)

* 0.0042 (0.0016) C7 * -0.0007 (0.0017) C8 * -0.0028 (0.0017) C9 * 0.0029 (0.0018) C10 * 0.0007 (0.0018) C11 * -0.0042 (0.0017) C12

Rms deviation of fitted atoms = 0.0030

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20074 (8)0.56421 (5)0.90658 (4)0.0323 (2)
S10.02394 (8)0.15154 (5)0.75439 (4)0.0270 (2)
C20.1444 (3)0.09324 (19)0.67277 (15)0.0240 (5)
N210.1131 (3)0.02602 (18)0.60550 (15)0.0293 (5)
H210.198 (4)0.014 (2)0.5597 (18)0.033 (7)*
H220.003 (4)0.026 (2)0.5980 (19)0.044 (8)*
N30.3039 (3)0.12351 (18)0.68956 (14)0.0261 (5)
H30.402 (4)0.098 (3)0.660 (2)0.040 (8)*
C40.2999 (3)0.1947 (2)0.76714 (16)0.0265 (5)
C50.1334 (3)0.2181 (2)0.81063 (16)0.0267 (5)
C60.0676 (3)0.2906 (2)0.89428 (16)0.0302 (6)
H610.17050.31230.92380.038*
H620.01480.36040.87360.038*
C70.0710 (3)0.2316 (2)0.96556 (15)0.0272 (5)
C80.2520 (3)0.2491 (2)0.96837 (16)0.0302 (6)
H80.28860.30120.92590.038*
C90.3825 (3)0.1929 (2)1.03128 (16)0.0315 (6)
H90.50630.20641.03170.039*
C100.3299 (3)0.1171 (2)1.09339 (17)0.0309 (6)
O10.4440 (3)0.05801 (15)1.16006 (13)0.0414 (5)
C110.1490 (4)0.0980 (2)1.09124 (18)0.0364 (6)
H110.11250.04591.13370.045*
C120.0218 (4)0.1539 (2)1.02825 (18)0.0346 (6)
H120.10180.13931.02740.043*
C130.4737 (3)0.2328 (2)0.79016 (18)0.0364 (6)
H1310.52960.17060.81860.046*
H1320.55360.25710.73270.046*
H1330.45250.29590.83430.046*
C140.6315 (4)0.0671 (3)1.1596 (2)0.0446 (7)
H1410.65930.02941.10390.056*
H1420.69920.03141.21590.056*
H1430.66490.14671.15850.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0237 (3)0.0452 (4)0.0281 (3)0.0040 (3)0.0048 (2)0.0053 (3)
S10.0204 (3)0.0343 (4)0.0261 (3)0.0002 (2)0.0039 (2)0.0042 (2)
C20.0217 (12)0.0260 (12)0.0248 (12)0.0010 (10)0.0056 (9)0.0029 (9)
N210.0242 (12)0.0387 (13)0.0256 (11)0.0035 (10)0.0060 (9)0.0064 (9)
N30.0194 (10)0.0348 (11)0.0239 (10)0.0005 (9)0.0037 (8)0.0014 (9)
C40.0258 (12)0.0302 (13)0.0243 (12)0.0013 (10)0.0067 (9)0.0002 (10)
C50.0256 (12)0.0292 (13)0.0265 (12)0.0007 (10)0.0074 (9)0.0009 (10)
C60.0281 (13)0.0342 (14)0.0281 (12)0.0012 (11)0.0044 (10)0.0051 (10)
C70.0286 (13)0.0302 (13)0.0233 (12)0.0003 (10)0.0059 (9)0.0059 (10)
C80.0304 (13)0.0353 (14)0.0257 (12)0.0027 (11)0.0073 (10)0.0011 (10)
C90.0253 (13)0.0397 (14)0.0307 (13)0.0018 (11)0.0080 (10)0.0036 (11)
C100.0334 (14)0.0315 (13)0.0267 (12)0.0003 (11)0.0027 (10)0.0035 (10)
O10.0364 (11)0.0451 (11)0.0412 (11)0.0050 (9)0.0029 (8)0.0116 (9)
C110.0378 (15)0.0368 (15)0.0353 (14)0.0065 (12)0.0089 (12)0.0048 (12)
C120.0284 (14)0.0414 (16)0.0344 (14)0.0052 (12)0.0069 (11)0.0019 (11)
C130.0257 (13)0.0481 (16)0.0373 (14)0.0004 (12)0.0106 (11)0.0074 (12)
C140.0371 (16)0.0478 (18)0.0460 (16)0.0068 (13)0.0002 (13)0.0042 (13)
Geometric parameters (Å, º) top
S1—C21.721 (2)C8—C91.388 (3)
S1—C51.751 (2)C8—H80.9500
C2—N211.316 (3)C9—C101.383 (4)
C2—N31.324 (3)C9—H90.9500
N21—H210.85 (3)C10—O11.368 (3)
N21—H220.91 (3)C10—C111.384 (4)
N3—C41.404 (3)O1—C141.426 (3)
N3—H30.84 (3)C11—C121.373 (4)
C4—C51.333 (3)C11—H110.9500
C4—C131.487 (3)C12—H120.9500
C5—C61.499 (3)C13—H1310.9800
C6—C71.507 (3)C13—H1320.9800
C6—H610.9900C13—H1330.9800
C6—H620.9900C14—H1410.9800
C7—C81.380 (3)C14—H1420.9800
C7—C121.394 (3)C14—H1430.9800
C2—S1—C591.19 (11)C9—C8—H8118.9
N21—C2—N3126.5 (2)C10—C9—C8119.1 (2)
N21—C2—S1122.97 (19)C10—C9—H9120.4
N3—C2—S1110.52 (17)C8—C9—H9120.4
C2—N21—H21118.4 (18)O1—C10—C11115.3 (2)
C2—N21—H22113.4 (18)O1—C10—C9125.1 (2)
H21—N21—H22121 (3)C11—C10—C9119.5 (2)
C2—N3—C4115.1 (2)C10—O1—C14117.3 (2)
C2—N3—H3124 (2)C12—C11—C10120.6 (2)
C4—N3—H3120 (2)C12—C11—H11119.7
C5—C4—N3112.7 (2)C10—C11—H11119.7
C5—C4—C13129.1 (2)C11—C12—C7121.1 (2)
N3—C4—C13118.2 (2)C11—C12—H12119.5
C4—C5—C6130.6 (2)C7—C12—H12119.5
C4—C5—S1110.50 (18)C4—C13—H131109.5
C6—C5—S1118.88 (17)C4—C13—H132109.5
C5—C6—C7112.1 (2)H131—C13—H132109.5
C5—C6—H61109.2C4—C13—H133109.5
C7—C6—H61109.2H131—C13—H133109.5
C5—C6—H62109.2H132—C13—H133109.5
C7—C6—H62109.2O1—C14—H141109.5
H61—C6—H62107.9O1—C14—H142109.5
C8—C7—C12117.5 (2)H141—C14—H142109.5
C8—C7—C6121.0 (2)O1—C14—H143109.5
C12—C7—C6121.4 (2)H141—C14—H143109.5
C7—C8—C9122.1 (2)H142—C14—H143109.5
C7—C8—H8118.9
C5—S1—C2—N21178.6 (2)C5—C6—C7—C897.2 (3)
C5—S1—C2—N30.21 (18)C5—C6—C7—C1280.0 (3)
N21—C2—N3—C4178.8 (2)C12—C7—C8—C90.5 (4)
S1—C2—N3—C40.5 (3)C6—C7—C8—C9177.8 (2)
C2—N3—C4—C50.5 (3)C7—C8—C9—C100.1 (4)
C2—N3—C4—C13179.7 (2)C8—C9—C10—O1178.6 (2)
N3—C4—C5—C6179.1 (2)C8—C9—C10—C110.5 (4)
C13—C4—C5—C61.2 (5)C11—C10—O1—C14174.5 (2)
N3—C4—C5—S10.3 (3)C9—C10—O1—C146.4 (4)
C13—C4—C5—S1179.9 (2)O1—C10—C11—C12179.0 (2)
C2—S1—C5—C40.09 (19)C9—C10—C11—C120.1 (4)
C2—S1—C5—C6179.0 (2)C10—C11—C12—C70.5 (4)
C4—C5—C6—C7131.3 (3)C8—C7—C12—C110.9 (4)
S1—C5—C6—C750.1 (3)C6—C7—C12—C11178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···Cl1i0.84 (3)2.33 (3)3.155 (2)167 (3)
N21—H21···Cl1ii0.85 (3)2.40 (3)3.162 (2)150 (2)
N21—H22···Cl1iii0.91 (3)2.30 (3)3.193 (2)168 (3)
Symmetry codes: (i) x1/2, y1/2, z+3/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC12H15ClN2OS
Mr270.77
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)7.5746 (15), 11.878 (2), 14.519 (3)
β (°) 100.47 (3)
V3)1284.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.45
Crystal size (mm)0.20 × 0.08 × 0.06
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.916, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
6971, 2796, 2125
Rint0.073
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.136, 1.01
No. of reflections2796
No. of parameters168
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.55

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, DENZOand COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···Cl1i0.84 (3)2.33 (3)3.155 (2)167 (3)
N21—H21···Cl1ii0.85 (3)2.40 (3)3.162 (2)150 (2)
N21—H22···Cl1iii0.91 (3)2.30 (3)3.193 (2)168 (3)
Symmetry codes: (i) x1/2, y1/2, z+3/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+3/2.
 

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