Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Benzo­thia­zole derivatives are a class of privileged mol­ecules due to their biological activity and pharmaceutical applications. One route to these mol­ecules is via intra­molecular cyclization of thio­ureas to form substituted 2-amino­benzo­thia­zoles, but this often requires harsh conditions or employs expensive metal catalysts. Herein, the copper(II)- and gold(III)-mediated cyclizations of thio­ureas to substituted 2-amino­benzo­thia­zoles are reported. The single-crystal X-ray structures of the thio­urea N-(3-meth­oxy­phen­yl)-N′-(pyridin-2-yl)thio­urea, C13H13N3OS, and the inter­mediate metal complexes aqua­bis­[5-meth­oxy-N-(pyridin-2-yl-κN)-1,3-benzo­thia­zol-2-amine-κN3]copper(II)­ dinitrate, [Cu(C13H11N3OS)2(H2O)](NO3)2, and bis­{2-[(5-meth­oxy-1,3-benzo­thia­zol-2-yl)amino]­pyridin-1-ium} di­chlorido­gold(I) chloride monohydrate, (C13H12N3OS)2[AuCl2]Cl·H2O, are reported. The copper complex exhibits a distorted trigonal–bipyramidal geometry, with direct metal-to-benzo­thia­zole-ligand coordination, while the gold complex is a salt containing the protonated uncoordinated benzo­thia­zole, and offers evidence that metal reduction (in this case, AuIII to AuI) is required for the cyclization to proceed. As such, this study provides further mechanistic insight into the role of the metal cations in these transformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961701381X/yf3126sup1.cif
Contains datablocks n17037, b17199, b18056, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701381X/yf3126n17037sup2.hkl
Contains datablock n17037

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701381X/yf3126b17199sup3.hkl
Contains datablock b17199

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701381X/yf3126b18056sup4.hkl
Contains datablock b18056

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205322961701381X/yf3126sup5.pdf
Additional experimental details and an NMR spectrum

CCDC references: 1576424; 1576423; 1576422

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-(3-Methoxyphenyl)-N'-(pyridin-2-yl)thiourea (n17037) top
Crystal data top
C13H13N3OSZ = 2
Mr = 259.32F(000) = 272
Triclinic, P1Dx = 1.374 Mg m3
a = 8.4341 (2) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.6991 (2) ÅCell parameters from 11716 reflections
c = 10.1083 (2) Åθ = 4.8–65.6°
α = 91.249 (2)°µ = 2.22 mm1
β = 113.506 (2)°T = 173 K
γ = 110.292 (2)°Prism, colorless
V = 626.73 (3) Å30.50 × 0.32 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer
2125 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source2096 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 65.6°, θmin = 4.9°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 99
Tmin = 0.668, Tmax = 1.000k = 109
12480 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2867P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2125 reflectionsΔρmax = 0.25 e Å3
172 parametersΔρmin = 0.26 e Å3
1 restraint
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.37970 (5)0.74874 (4)0.88794 (4)0.02876 (15)
O10.28022 (18)0.16770 (13)0.55060 (13)0.0385 (3)
N10.87028 (18)1.03625 (15)0.77940 (14)0.0266 (3)
N20.69580 (18)0.98474 (15)0.91734 (14)0.0236 (3)
H20.680 (3)1.026 (2)0.9837 (19)0.031 (5)*
N30.55882 (18)0.76960 (15)0.71919 (14)0.0244 (3)
H30.648 (3)0.821 (2)0.701 (2)0.040 (5)*
C11.0155 (2)1.1378 (2)0.75682 (18)0.0305 (4)
H11.0328371.1022590.6758410.037*
C21.1401 (2)1.29027 (19)0.84484 (18)0.0303 (4)
H2A1.2408601.3584620.8253160.036*
C31.1143 (2)1.34169 (19)0.96316 (18)0.0297 (4)
H3A1.1975441.4465261.0259150.036*
C40.9675 (2)1.23997 (19)0.98894 (17)0.0268 (3)
H40.9481821.2724571.0698140.032*
C50.84737 (19)1.08752 (17)0.89301 (15)0.0215 (3)
C60.5532 (2)0.83663 (17)0.83584 (15)0.0215 (3)
C70.4118 (2)0.62124 (18)0.61906 (16)0.0225 (3)
C80.4249 (2)0.46847 (18)0.64025 (16)0.0239 (3)
H80.5284260.4616360.7210880.029*
C90.2840 (2)0.32518 (18)0.54118 (16)0.0247 (3)
C100.1332 (2)0.33607 (19)0.42311 (17)0.0297 (4)
H100.0368180.2380220.3559950.036*
C110.1238 (2)0.4893 (2)0.40360 (18)0.0349 (4)
H110.0208190.4964610.3224310.042*
C120.2633 (2)0.6337 (2)0.50136 (18)0.0313 (4)
H120.2566190.7393420.4874190.038*
C130.4251 (3)0.1471 (2)0.6749 (2)0.0457 (5)
H13A0.4025960.0283610.6703130.069*
H13B0.4254430.1909580.7651380.069*
H13C0.5468030.2079550.6743840.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0302 (2)0.0208 (2)0.0309 (2)0.00158 (16)0.01936 (18)0.00503 (15)
O10.0508 (7)0.0212 (6)0.0308 (6)0.0126 (5)0.0071 (5)0.0007 (5)
N10.0268 (7)0.0217 (6)0.0297 (7)0.0043 (5)0.0155 (6)0.0001 (5)
N20.0258 (6)0.0191 (6)0.0226 (6)0.0028 (5)0.0126 (5)0.0036 (5)
N30.0230 (7)0.0203 (6)0.0260 (7)0.0017 (5)0.0131 (5)0.0042 (5)
C10.0311 (8)0.0276 (8)0.0350 (9)0.0076 (7)0.0198 (7)0.0035 (7)
C20.0268 (8)0.0248 (8)0.0388 (9)0.0057 (6)0.0174 (7)0.0077 (7)
C30.0252 (8)0.0206 (7)0.0316 (8)0.0014 (6)0.0076 (7)0.0001 (6)
C40.0270 (8)0.0235 (8)0.0246 (8)0.0053 (6)0.0100 (6)0.0012 (6)
C50.0210 (7)0.0193 (7)0.0220 (7)0.0070 (6)0.0082 (6)0.0034 (6)
C60.0232 (7)0.0165 (7)0.0220 (7)0.0063 (6)0.0087 (6)0.0005 (6)
C70.0224 (7)0.0202 (7)0.0232 (7)0.0035 (6)0.0127 (6)0.0041 (6)
C80.0257 (8)0.0252 (8)0.0198 (7)0.0088 (6)0.0101 (6)0.0002 (6)
C90.0329 (8)0.0196 (7)0.0218 (7)0.0076 (6)0.0145 (6)0.0006 (6)
C100.0281 (8)0.0245 (8)0.0253 (8)0.0037 (6)0.0072 (6)0.0058 (6)
C110.0292 (8)0.0332 (9)0.0304 (9)0.0116 (7)0.0024 (7)0.0021 (7)
C120.0332 (9)0.0240 (8)0.0338 (9)0.0126 (7)0.0107 (7)0.0002 (7)
C130.0624 (12)0.0315 (9)0.0382 (10)0.0249 (9)0.0114 (9)0.0076 (8)
Geometric parameters (Å, º) top
S1—C61.6910 (15)C3—C41.375 (2)
O1—C91.3655 (19)C4—H40.9500
O1—C131.428 (2)C4—C51.398 (2)
N1—C11.347 (2)C7—C81.386 (2)
N1—C51.3303 (19)C7—C121.381 (2)
N2—H20.833 (17)C8—H80.9500
N2—C51.4007 (19)C8—C91.392 (2)
N2—C61.3689 (19)C9—C101.389 (2)
N3—H30.828 (17)C10—H100.9500
N3—C61.3290 (19)C10—C111.377 (2)
N3—C71.4352 (18)C11—H110.9500
C1—H10.9500C11—C121.390 (2)
C1—C21.375 (2)C12—H120.9500
C2—H2A0.9500C13—H13A0.9800
C2—C31.389 (2)C13—H13B0.9800
C3—H3A0.9500C13—H13C0.9800
C9—O1—C13117.87 (13)N3—C6—N2117.86 (13)
C5—N1—C1117.73 (13)C8—C7—N3119.07 (13)
C5—N2—H2115.5 (13)C12—C7—N3119.58 (13)
C6—N2—H2113.8 (13)C12—C7—C8121.32 (14)
C6—N2—C5129.96 (13)C7—C8—H8120.5
C6—N3—H3117.5 (14)C7—C8—C9118.93 (14)
C6—N3—C7123.30 (13)C9—C8—H8120.5
C7—N3—H3119.1 (14)O1—C9—C8124.51 (14)
N1—C1—H1118.3O1—C9—C10115.24 (13)
N1—C1—C2123.43 (15)C10—C9—C8120.24 (14)
C2—C1—H1118.3C9—C10—H10120.1
C1—C2—H2A121.0C11—C10—C9119.82 (14)
C1—C2—C3118.07 (14)C11—C10—H10120.1
C3—C2—H2A121.0C10—C11—H11119.6
C2—C3—H3A120.2C10—C11—C12120.72 (15)
C4—C3—C2119.63 (14)C12—C11—H11119.6
C4—C3—H3A120.2C7—C12—C11118.96 (15)
C3—C4—H4120.9C7—C12—H12120.5
C3—C4—C5118.25 (14)C11—C12—H12120.5
C5—C4—H4120.9O1—C13—H13A109.5
N1—C5—N2118.64 (13)O1—C13—H13B109.5
N1—C5—C4122.89 (13)O1—C13—H13C109.5
C4—C5—N2118.47 (13)H13A—C13—H13B109.5
N2—C6—S1118.69 (11)H13A—C13—H13C109.5
N3—C6—S1123.46 (11)H13B—C13—H13C109.5
O1—C9—C10—C11179.94 (15)C6—N2—C5—C4175.50 (14)
N1—C1—C2—C30.0 (2)C6—N3—C7—C894.15 (17)
N3—C7—C8—C9178.66 (13)C6—N3—C7—C1287.82 (19)
N3—C7—C12—C11178.71 (14)C7—N3—C6—S14.4 (2)
C1—N1—C5—N2179.20 (13)C7—N3—C6—N2175.49 (13)
C1—N1—C5—C40.5 (2)C7—C8—C9—O1179.53 (14)
C1—C2—C3—C40.2 (2)C7—C8—C9—C100.1 (2)
C2—C3—C4—C50.6 (2)C8—C7—C12—C110.7 (2)
C3—C4—C5—N10.7 (2)C8—C9—C10—C110.4 (2)
C3—C4—C5—N2178.94 (13)C9—C10—C11—C120.3 (3)
C5—N1—C1—C20.1 (2)C10—C11—C12—C70.2 (3)
C5—N2—C6—S1175.35 (12)C12—C7—C8—C90.7 (2)
C5—N2—C6—N34.6 (2)C13—O1—C9—C83.6 (2)
C6—N2—C5—N14.2 (2)C13—O1—C9—C10176.05 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···S1i0.83 (2)2.62 (2)3.3882 (13)154 (2)
N3—H3···N10.83 (2)1.99 (2)2.6624 (17)138 (2)
Symmetry code: (i) x+1, y+2, z+2.
Aquabis[5-methoxy-N-(pyridin-2-yl-κN)benzothiazol-2-amine-κN3]copper(II) dinitrate (b17199) top
Crystal data top
[Cu(C13H11N3OS)2(H2O)](NO3)2Dx = 1.679 Mg m3
Mr = 720.19Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 62086 reflections
a = 18.1534 (4) Åθ = 2.2–39.5°
b = 7.1814 (1) ŵ = 0.98 mm1
c = 21.8523 (4) ÅT = 110 K
V = 2848.81 (9) Å3Prism, green
Z = 40.33 × 0.23 × 0.17 mm
F(000) = 1476
Data collection top
Bruker APEXII CCD
diffractometer
2703 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2703 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω and φ scansθmax = 25.7°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 2217
Tmin = 0.835, Tmax = 1.000k = 88
72311 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0189P)2 + 9.2626P]
where P = (Fo2 + 2Fc2)/3
S = 1.34(Δ/σ)max < 0.001
2703 reflectionsΔρmax = 0.79 e Å3
215 parametersΔρmin = 0.66 e Å3
3 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.5000000.47025 (8)0.7500000.01397 (16)
S10.35592 (5)0.40264 (13)0.58540 (4)0.0215 (2)
O10.66894 (15)0.2340 (4)0.56003 (12)0.0299 (6)
O20.5000000.1889 (5)0.7500000.0364 (10)
H2A0.5393 (11)0.1272 (12)0.759 (3)0.055*0.5
H2B0.468 (2)0.1274 (12)0.729 (2)0.055*0.5
N10.41384 (14)0.6490 (4)0.77375 (12)0.0149 (6)
N20.33369 (15)0.5337 (4)0.69802 (13)0.0179 (6)
H20.2892 (12)0.525 (6)0.6845 (16)0.021*
N30.45591 (15)0.4536 (4)0.66819 (12)0.0145 (6)
C10.42390 (19)0.7627 (5)0.82261 (15)0.0190 (7)
H10.4725900.7820920.8372170.023*
C20.3669 (2)0.8512 (5)0.85188 (16)0.0238 (8)
H2C0.3759350.9313560.8856210.029*
C30.2957 (2)0.8207 (5)0.83105 (16)0.0245 (8)
H30.2550620.8736490.8521650.029*
C40.28424 (18)0.7144 (5)0.78011 (16)0.0204 (7)
H40.2360040.6958420.7643970.024*
C50.34564 (18)0.6334 (4)0.75162 (15)0.0166 (7)
C60.38493 (18)0.4711 (5)0.65788 (14)0.0159 (7)
C70.49227 (19)0.3806 (4)0.61717 (15)0.0179 (7)
C80.5671 (2)0.3422 (5)0.61330 (15)0.0209 (7)
H80.5987380.3649500.6470940.025*
C90.5946 (2)0.2700 (5)0.55917 (16)0.0229 (8)
C100.5492 (2)0.2336 (5)0.50918 (16)0.0248 (8)
H100.5692350.1832350.4726010.030*
C110.4744 (2)0.2715 (5)0.51330 (16)0.0246 (8)
H110.4427960.2480010.4795450.030*
C120.44650 (19)0.3441 (5)0.56721 (15)0.0199 (7)
C130.7001 (2)0.1407 (6)0.50876 (18)0.0347 (10)
H13A0.6962660.2203850.4725040.052*
H13B0.6734520.0240680.5015160.052*
H13C0.7520630.1133050.5169610.052*
O30.36773 (14)0.0698 (4)0.70721 (12)0.0281 (6)
O40.29737 (14)0.0570 (4)0.63928 (12)0.0302 (6)
O50.41492 (14)0.0873 (4)0.63256 (13)0.0340 (7)
N40.36037 (15)0.0238 (4)0.65980 (13)0.0197 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0135 (3)0.0163 (3)0.0122 (3)0.0000.0014 (2)0.000
S10.0219 (4)0.0260 (5)0.0168 (4)0.0031 (4)0.0056 (3)0.0002 (3)
O10.0295 (14)0.0349 (15)0.0252 (13)0.0057 (12)0.0083 (11)0.0043 (12)
O20.046 (3)0.0155 (18)0.048 (2)0.0000.033 (2)0.000
N10.0120 (13)0.0151 (13)0.0177 (13)0.0017 (11)0.0007 (10)0.0004 (11)
N20.0121 (13)0.0196 (15)0.0218 (14)0.0023 (11)0.0011 (11)0.0020 (12)
N30.0183 (14)0.0141 (14)0.0112 (12)0.0012 (11)0.0000 (10)0.0014 (11)
C10.0197 (17)0.0173 (16)0.0200 (16)0.0001 (13)0.0019 (13)0.0021 (14)
C20.032 (2)0.0183 (18)0.0214 (17)0.0021 (15)0.0020 (15)0.0016 (14)
C30.0248 (18)0.0224 (18)0.0264 (18)0.0071 (15)0.0091 (15)0.0028 (15)
C40.0143 (16)0.0193 (17)0.0276 (18)0.0011 (13)0.0016 (14)0.0063 (15)
C50.0180 (16)0.0117 (15)0.0202 (16)0.0021 (12)0.0008 (13)0.0037 (13)
C60.0215 (16)0.0136 (16)0.0127 (15)0.0039 (13)0.0017 (13)0.0024 (13)
C70.0266 (18)0.0109 (15)0.0162 (15)0.0008 (14)0.0011 (13)0.0016 (12)
C80.0248 (18)0.0191 (17)0.0189 (16)0.0013 (15)0.0002 (14)0.0018 (14)
C90.0259 (18)0.0180 (17)0.0249 (18)0.0003 (15)0.0053 (15)0.0007 (15)
C100.038 (2)0.0168 (17)0.0194 (18)0.0019 (16)0.0061 (15)0.0022 (14)
C110.038 (2)0.0204 (18)0.0155 (17)0.0066 (16)0.0015 (15)0.0000 (14)
C120.0251 (18)0.0169 (16)0.0178 (16)0.0037 (14)0.0003 (14)0.0029 (14)
C130.040 (2)0.036 (2)0.028 (2)0.0104 (19)0.0169 (17)0.0028 (18)
O30.0310 (14)0.0261 (14)0.0272 (13)0.0052 (11)0.0005 (11)0.0018 (12)
O40.0180 (13)0.0412 (17)0.0314 (14)0.0043 (12)0.0017 (11)0.0054 (13)
O50.0202 (13)0.0452 (17)0.0367 (15)0.0088 (13)0.0059 (11)0.0007 (14)
N40.0165 (14)0.0191 (15)0.0234 (15)0.0001 (12)0.0011 (12)0.0047 (12)
Geometric parameters (Å, º) top
Cu1—O22.020 (4)C2—H2C0.9500
Cu1—N1i2.089 (3)C2—C31.387 (5)
Cu1—N12.089 (3)C3—H30.9500
Cu1—N3i1.962 (3)C3—C41.366 (5)
Cu1—N31.962 (3)C4—H40.9500
S1—C61.740 (3)C4—C51.403 (5)
S1—C121.743 (4)C7—C81.388 (5)
O1—C91.374 (4)C7—C121.397 (5)
O1—C131.423 (4)C8—H80.9500
O2—H2Ai0.861 (7)C8—C91.385 (5)
O2—H2A0.861 (14)C9—C101.393 (5)
O2—H2Bi0.861 (7)C10—H100.9500
O2—H2B0.861 (14)C10—C111.387 (5)
N1—C11.357 (4)C11—H110.9500
N1—C51.334 (4)C11—C121.384 (5)
N2—H20.861 (18)C13—H13A0.9800
N2—C51.390 (4)C13—H13B0.9800
N2—C61.355 (4)C13—H13C0.9800
N3—C61.314 (4)O3—N41.242 (4)
N3—C71.398 (4)O4—N41.251 (4)
C1—H10.9500O5—N41.242 (4)
C1—C21.372 (5)
O2—Cu1—N1127.91 (8)C4—C3—H3120.1
O2—Cu1—N1i127.91 (7)C3—C4—H4120.9
N1i—Cu1—N1104.18 (15)C3—C4—C5118.2 (3)
N3—Cu1—O286.51 (8)C5—C4—H4120.9
N3i—Cu1—O286.51 (8)N1—C5—N2119.6 (3)
N3—Cu1—N187.61 (11)N1—C5—C4122.8 (3)
N3—Cu1—N1i96.69 (11)N2—C5—C4117.6 (3)
N3i—Cu1—N1i87.61 (11)N2—C6—S1118.4 (2)
N3i—Cu1—N196.69 (11)N3—C6—S1115.2 (2)
N3—Cu1—N3i173.03 (16)N3—C6—N2126.4 (3)
C6—S1—C1289.44 (16)C8—C7—N3125.8 (3)
C9—O1—C13117.9 (3)C8—C7—C12119.8 (3)
Cu1—O2—H2A121.0C12—C7—N3114.4 (3)
Cu1—O2—H2Ai121.0 (8)C7—C8—H8120.7
Cu1—O2—H2B120.9C9—C8—C7118.6 (3)
Cu1—O2—H2Bi120.9 (8)C9—C8—H8120.7
H2A—O2—H2Ai118.0O1—C9—C8114.4 (3)
H2A—O2—H2B114.6O1—C9—C10123.8 (3)
H2Ai—O2—H2Bi114.6C8—C9—C10121.8 (3)
H2B—O2—H2Bi118.2C9—C10—H10120.3
C1—N1—Cu1117.7 (2)C11—C10—C9119.4 (3)
C5—N1—Cu1123.6 (2)C11—C10—H10120.3
C5—N1—C1117.4 (3)C10—C11—H11120.4
C5—N2—H2118 (3)C12—C11—C10119.2 (3)
C6—N2—H2113 (3)C12—C11—H11120.4
C6—N2—C5127.5 (3)C7—C12—S1109.7 (3)
C6—N3—Cu1123.4 (2)C11—C12—S1129.1 (3)
C6—N3—C7111.2 (3)C11—C12—C7121.2 (3)
C7—N3—Cu1123.8 (2)O1—C13—H13A109.5
N1—C1—H1118.5O1—C13—H13B109.5
N1—C1—C2122.9 (3)O1—C13—H13C109.5
C2—C1—H1118.5H13A—C13—H13B109.5
C1—C2—H2C120.8H13A—C13—H13C109.5
C1—C2—C3118.5 (3)H13B—C13—H13C109.5
C3—C2—H2C120.8O3—N4—O4120.0 (3)
C2—C3—H3120.1O3—N4—O5120.8 (3)
C4—C3—C2119.9 (3)O5—N4—O4119.1 (3)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O30.861.922.715 (3)151 (3)
O2—H2A···O3i0.861.892.715 (3)160
N2—H2···O4ii0.86 (2)1.95 (2)2.781 (4)162 (4)
C1—H1···O5iii0.952.343.268 (4)165
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1/2, y+1/2, z; (iii) x+1, y+1, z+3/2.
Bis{2-[(5-methoxy-1,3-benzothiazol-2-yl)amino]pyridin-1-ium} dichloridogold(I) chloride monohydrate (b18056) top
Crystal data top
(C13H12N3OS)2[AuCl2]Cl·H2OZ = 2
Mr = 837.96F(000) = 820
Triclinic, P1Dx = 1.907 Mg m3
a = 10.0052 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5940 (2) ÅCell parameters from 104589 reflections
c = 12.9412 (1) Åθ = 2.0–50.4°
α = 111.867 (1)°µ = 5.50 mm1
β = 97.271 (1)°T = 110 K
γ = 99.755 (1)°Prism, colorless
V = 1459.03 (3) Å30.31 × 0.11 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
5973 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source5961 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω and φ scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1212
Tmin = 0.473, Tmax = 1.000k = 1515
85384 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.018H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.041 w = 1/[σ2(Fo2) + (0.0122P)2 + 2.4258P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.004
5973 reflectionsΔρmax = 0.76 e Å3
396 parametersΔρmin = 0.85 e Å3
5 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S20.41939 (6)0.75769 (5)0.72552 (5)0.01731 (12)
O20.69431 (19)0.54362 (16)0.99756 (15)0.0200 (4)
N40.6790 (2)0.59876 (18)0.46614 (18)0.0151 (4)
H40.685 (3)0.588 (3)0.524 (2)0.026 (9)*
N50.5244 (2)0.71619 (19)0.53596 (18)0.0166 (4)
H50.475 (3)0.762 (2)0.527 (3)0.030 (9)*
N60.6055 (2)0.63748 (18)0.66463 (17)0.0162 (4)
C140.7519 (3)0.5493 (2)0.3865 (2)0.0188 (5)
H140.8098580.5007150.3983920.023*
C150.7421 (3)0.5692 (2)0.2899 (2)0.0203 (5)
H150.7922970.5343570.2336770.024*
C160.6570 (3)0.6418 (2)0.2745 (2)0.0192 (5)
H160.6502520.6573220.2078530.023*
C170.5831 (3)0.6909 (2)0.3550 (2)0.0176 (5)
H170.5248680.7396850.3440540.021*
C180.5944 (2)0.6682 (2)0.4532 (2)0.0147 (5)
C190.5267 (2)0.6976 (2)0.6343 (2)0.0151 (5)
C200.5867 (2)0.6376 (2)0.7700 (2)0.0154 (5)
C210.6560 (2)0.5815 (2)0.8265 (2)0.0158 (5)
H210.7191880.5371890.7936010.019*
C220.6301 (2)0.5923 (2)0.9322 (2)0.0162 (5)
C230.5347 (3)0.6558 (2)0.9798 (2)0.0169 (5)
H230.5183750.6614931.0522170.020*
C240.4644 (3)0.7100 (2)0.9233 (2)0.0180 (5)
H240.3995450.7525260.9555700.022*
C250.4912 (2)0.7005 (2)0.8175 (2)0.0149 (5)
C260.7772 (3)0.4653 (3)0.9462 (2)0.0249 (6)
H26A0.7211120.4014570.8759880.037*
H26B0.8118270.4322010.9989160.037*
H26C0.8557570.5083480.9282600.037*
S10.67232 (6)1.00715 (5)0.96345 (5)0.01600 (12)
O10.93392 (19)0.79817 (16)1.24720 (14)0.0197 (4)
N10.9505 (2)0.85301 (18)0.71852 (18)0.0162 (4)
H10.960 (3)0.849 (3)0.779 (2)0.025 (8)*
N20.7788 (2)0.95630 (18)0.77372 (17)0.0158 (4)
H20.723 (3)0.993 (3)0.755 (3)0.041 (10)*
N30.8627 (2)0.88981 (18)0.91125 (17)0.0149 (4)
C11.0317 (3)0.8078 (2)0.6446 (2)0.0195 (5)
H1A1.0971520.7680190.6635290.023*
C21.0195 (3)0.8194 (2)0.5435 (2)0.0219 (5)
H2A1.0759070.7878380.4914320.026*
C30.9224 (3)0.8786 (2)0.5176 (2)0.0204 (5)
H30.9118220.8863350.4469180.024*
C40.8424 (3)0.9256 (2)0.5936 (2)0.0182 (5)
H4A0.7776860.9669030.5765470.022*
C50.8574 (2)0.9118 (2)0.6971 (2)0.0155 (5)
C60.7823 (2)0.9451 (2)0.8760 (2)0.0140 (5)
C70.8413 (2)0.8923 (2)1.0163 (2)0.0143 (5)
C80.9101 (2)0.8387 (2)1.0766 (2)0.0148 (5)
H80.9786270.7984341.0484710.018*
C90.8748 (3)0.8464 (2)1.1788 (2)0.0161 (5)
C100.7728 (3)0.9049 (2)1.2202 (2)0.0177 (5)
H100.7501850.9079101.2902120.021*
C110.7047 (3)0.9584 (2)1.1609 (2)0.0179 (5)
H110.6358120.9980711.1890500.021*
C120.7408 (2)0.9520 (2)1.0584 (2)0.0146 (5)
C131.0300 (3)0.7290 (2)1.2054 (2)0.0228 (5)
H13A0.9849460.6646471.1317470.034*
H13B1.0607460.6963651.2596370.034*
H13C1.1102500.7786321.1960260.034*
Au10.95986 (2)0.55935 (2)0.71308 (2)0.01682 (3)
Cl11.11166 (7)0.70866 (6)0.86031 (6)0.02465 (13)
Cl20.80710 (7)0.41058 (6)0.56663 (6)0.02767 (14)
O30.3768 (2)0.87843 (19)0.5227 (2)0.0272 (4)
H3A0.425 (4)0.938 (3)0.566 (3)0.037 (11)*
H3B0.380 (4)0.885 (4)0.465 (3)0.053 (13)*
Cl30.58921 (7)1.10213 (6)0.71166 (6)0.02530 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0189 (3)0.0197 (3)0.0165 (3)0.0097 (2)0.0050 (2)0.0082 (2)
O20.0229 (9)0.0241 (9)0.0196 (9)0.0095 (8)0.0066 (7)0.0135 (8)
N40.0166 (10)0.0163 (10)0.0163 (10)0.0052 (8)0.0042 (8)0.0099 (8)
N50.0184 (10)0.0189 (10)0.0182 (10)0.0090 (8)0.0051 (8)0.0113 (9)
N60.0172 (10)0.0193 (10)0.0150 (10)0.0059 (8)0.0044 (8)0.0091 (8)
C140.0179 (12)0.0181 (12)0.0214 (13)0.0056 (10)0.0050 (10)0.0080 (10)
C150.0219 (13)0.0198 (12)0.0187 (12)0.0054 (10)0.0069 (10)0.0061 (10)
C160.0213 (13)0.0181 (12)0.0168 (12)0.0013 (10)0.0019 (10)0.0074 (10)
C170.0189 (12)0.0182 (12)0.0170 (12)0.0045 (10)0.0012 (10)0.0093 (10)
C180.0133 (11)0.0129 (11)0.0173 (12)0.0018 (9)0.0022 (9)0.0064 (9)
C190.0142 (11)0.0149 (11)0.0175 (12)0.0036 (9)0.0033 (9)0.0080 (10)
C200.0142 (11)0.0154 (11)0.0151 (11)0.0001 (9)0.0018 (9)0.0063 (9)
C210.0146 (11)0.0182 (12)0.0180 (12)0.0049 (9)0.0047 (9)0.0104 (10)
C220.0153 (11)0.0149 (11)0.0187 (12)0.0005 (9)0.0016 (9)0.0089 (10)
C230.0167 (12)0.0183 (12)0.0150 (11)0.0018 (9)0.0043 (9)0.0066 (10)
C240.0172 (12)0.0188 (12)0.0178 (12)0.0046 (10)0.0054 (10)0.0064 (10)
C250.0137 (11)0.0140 (11)0.0173 (12)0.0035 (9)0.0024 (9)0.0068 (9)
C260.0271 (14)0.0308 (15)0.0249 (14)0.0147 (12)0.0070 (11)0.0162 (12)
S10.0184 (3)0.0168 (3)0.0156 (3)0.0082 (2)0.0054 (2)0.0073 (2)
O10.0275 (10)0.0230 (9)0.0139 (8)0.0104 (8)0.0053 (7)0.0108 (7)
N10.0191 (10)0.0169 (10)0.0148 (10)0.0046 (8)0.0040 (8)0.0086 (9)
N20.0180 (10)0.0185 (10)0.0160 (10)0.0078 (8)0.0051 (8)0.0104 (8)
N30.0169 (10)0.0155 (10)0.0144 (10)0.0039 (8)0.0041 (8)0.0081 (8)
C10.0207 (13)0.0183 (12)0.0217 (13)0.0058 (10)0.0083 (10)0.0088 (10)
C20.0269 (14)0.0206 (13)0.0181 (12)0.0048 (11)0.0099 (11)0.0065 (10)
C30.0241 (13)0.0212 (13)0.0149 (12)0.0002 (10)0.0039 (10)0.0087 (10)
C40.0195 (12)0.0189 (12)0.0172 (12)0.0030 (10)0.0019 (10)0.0095 (10)
C50.0159 (11)0.0140 (11)0.0153 (11)0.0004 (9)0.0017 (9)0.0061 (9)
C60.0124 (11)0.0136 (11)0.0154 (11)0.0016 (9)0.0030 (9)0.0060 (9)
C70.0150 (11)0.0135 (11)0.0122 (11)0.0005 (9)0.0021 (9)0.0040 (9)
C80.0158 (11)0.0154 (11)0.0153 (11)0.0048 (9)0.0046 (9)0.0076 (9)
C90.0182 (12)0.0146 (11)0.0147 (11)0.0021 (9)0.0015 (9)0.0063 (9)
C100.0218 (13)0.0179 (12)0.0130 (11)0.0036 (10)0.0066 (10)0.0053 (10)
C110.0197 (12)0.0161 (12)0.0167 (12)0.0053 (10)0.0059 (10)0.0043 (10)
C120.0156 (11)0.0122 (11)0.0145 (11)0.0025 (9)0.0017 (9)0.0044 (9)
C130.0249 (13)0.0271 (14)0.0240 (13)0.0124 (11)0.0062 (11)0.0158 (11)
Au10.01572 (5)0.01910 (5)0.01926 (5)0.00721 (4)0.00532 (4)0.00985 (4)
Cl10.0202 (3)0.0280 (3)0.0226 (3)0.0066 (3)0.0017 (2)0.0073 (3)
Cl20.0290 (3)0.0211 (3)0.0284 (3)0.0057 (3)0.0016 (3)0.0074 (3)
O30.0301 (11)0.0249 (11)0.0333 (12)0.0103 (9)0.0100 (10)0.0163 (10)
Cl30.0242 (3)0.0298 (3)0.0319 (3)0.0131 (3)0.0070 (3)0.0202 (3)
Geometric parameters (Å, º) top
S2—C191.747 (2)O1—C91.376 (3)
S2—C251.746 (2)O1—C131.428 (3)
O2—C221.373 (3)N1—H10.80 (3)
O2—C261.426 (3)N1—C11.359 (3)
N4—H40.81 (3)N1—C51.347 (3)
N4—C141.360 (3)N2—H20.852 (15)
N4—C181.354 (3)N2—C51.360 (3)
N5—H50.851 (15)N2—C61.379 (3)
N5—C181.361 (3)N3—C61.294 (3)
N5—C191.375 (3)N3—C71.393 (3)
N6—C191.301 (3)C1—H1A0.9500
N6—C201.400 (3)C1—C21.363 (4)
C14—H140.9500C2—H2A0.9500
C14—C151.358 (4)C2—C31.401 (4)
C15—H150.9500C3—H30.9500
C15—C161.400 (4)C3—C41.373 (4)
C16—H160.9500C4—H4A0.9500
C16—C171.372 (4)C4—C51.406 (3)
C17—H170.9500C7—C81.397 (3)
C17—C181.398 (3)C7—C121.401 (3)
C20—C211.392 (3)C8—H80.9500
C20—C251.400 (3)C8—C91.385 (3)
C21—H210.9500C9—C101.404 (3)
C21—C221.386 (3)C10—H100.9500
C22—C231.403 (3)C10—C111.383 (4)
C23—H230.9500C11—H110.9500
C23—C241.378 (4)C11—C121.396 (3)
C24—H240.9500C13—H13A0.9800
C24—C251.394 (3)C13—H13B0.9800
C26—H26A0.9800C13—H13C0.9800
C26—H26B0.9800Au1—Cl12.2592 (7)
C26—H26C0.9800Au1—Cl22.2560 (7)
S1—C61.747 (2)O3—H3A0.78 (3)
S1—C121.745 (2)O3—H3B0.78 (3)
C25—S2—C1988.15 (11)C9—O1—C13117.33 (19)
C22—O2—C26117.14 (19)C1—N1—H1120 (2)
C14—N4—H4121 (2)C5—N1—H1117 (2)
C18—N4—H4117 (2)C5—N1—C1122.5 (2)
C18—N4—C14122.3 (2)C5—N2—H2115 (2)
C18—N5—H5118 (2)C5—N2—C6125.4 (2)
C18—N5—C19125.7 (2)C6—N2—H2119 (2)
C19—N5—H5117 (2)C6—N3—C7110.1 (2)
C19—N6—C20109.9 (2)N1—C1—H1A119.9
N4—C14—H14119.9N1—C1—C2120.3 (2)
C15—C14—N4120.2 (2)C2—C1—H1A119.9
C15—C14—H14119.9C1—C2—H2A120.6
C14—C15—H15120.6C1—C2—C3118.8 (2)
C14—C15—C16118.9 (2)C3—C2—H2A120.6
C16—C15—H15120.6C2—C3—H3119.8
C15—C16—H16119.7C4—C3—C2120.5 (2)
C17—C16—C15120.6 (2)C4—C3—H3119.8
C17—C16—H16119.7C3—C4—H4A120.4
C16—C17—H17120.4C3—C4—C5119.2 (2)
C16—C17—C18119.3 (2)C5—C4—H4A120.4
C18—C17—H17120.4N1—C5—N2120.6 (2)
N4—C18—N5119.9 (2)N1—C5—C4118.7 (2)
N4—C18—C17118.7 (2)N2—C5—C4120.6 (2)
N5—C18—C17121.3 (2)N2—C6—S1119.11 (18)
N5—C19—S2119.11 (18)N3—C6—S1117.41 (18)
N6—C19—S2117.11 (18)N3—C6—N2123.5 (2)
N6—C19—N5123.8 (2)N3—C7—C8124.4 (2)
N6—C20—C25114.7 (2)N3—C7—C12114.6 (2)
C21—C20—N6124.3 (2)C8—C7—C12121.0 (2)
C21—C20—C25120.9 (2)C7—C8—H8121.2
C20—C21—H21121.0C9—C8—C7117.5 (2)
C22—C21—C20117.9 (2)C9—C8—H8121.2
C22—C21—H21121.0O1—C9—C8124.0 (2)
O2—C22—C21123.5 (2)O1—C9—C10114.6 (2)
O2—C22—C23115.5 (2)C8—C9—C10121.5 (2)
C21—C22—C23121.0 (2)C9—C10—H10119.4
C22—C23—H23119.4C11—C10—C9121.2 (2)
C24—C23—C22121.2 (2)C11—C10—H10119.4
C24—C23—H23119.4C10—C11—H11121.1
C23—C24—H24121.0C10—C11—C12117.7 (2)
C23—C24—C25118.1 (2)C12—C11—H11121.1
C25—C24—H24121.0C7—C12—S1110.12 (17)
C20—C25—S2110.04 (18)C11—C12—S1128.73 (19)
C24—C25—S2129.11 (19)C11—C12—C7121.1 (2)
C24—C25—C20120.9 (2)O1—C13—H13A109.5
O2—C26—H26A109.5O1—C13—H13B109.5
O2—C26—H26B109.5O1—C13—H13C109.5
O2—C26—H26C109.5H13A—C13—H13B109.5
H26A—C26—H26B109.5H13A—C13—H13C109.5
H26A—C26—H26C109.5H13B—C13—H13C109.5
H26B—C26—H26C109.5Cl2—Au1—Cl1179.62 (3)
C12—S1—C687.80 (11)H3A—O3—H3B102 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O30.85 (2)1.91 (2)2.758 (3)173 (3)
N2—H2···Cl30.85 (2)2.23 (2)3.084 (2)176 (4)
C3—H3···O1i0.952.463.284 (3)145
O3—H3A···Cl30.78 (3)2.39 (3)3.155 (2)171 (4)
O3—H3B···Cl3ii0.78 (3)2.41 (3)3.188 (2)174 (4)
Symmetry codes: (i) x, y, z1; (ii) x+1, y+2, z+1.
Selected short intermolecular interactions for (HBL1)2[AuCl2]Cl.H2O, (II) top
Cg1 is the centroid of the N1/C1–C5] ring, Cg2that of the C7–C12 ring, Cg3 that of the N4/C14–C18] ring and Cg4 that of the C20–C25 ring.
CentroidsCg···Cg (Å)Dihedral Angle between Planes (°)
Cg1···Cg33.8422 (14)6.43 (8)
Cg2···Cg43.7491 (14)3.38 (8)
Cg1—Cg2i3.8172 (14)3.92 (8)
Cg3···Cg4ii3.7667 (14)3.00 (8)
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+1, -z+1.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds