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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
CCDC references: 1576424; 1576423; 1576422
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
C13H13N3OS | Z = 2 |
Mr = 259.32 | F(000) = 272 |
Triclinic, P1 | Dx = 1.374 Mg m−3 |
a = 8.4341 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.6991 (2) Å | Cell parameters from 11716 reflections |
c = 10.1083 (2) Å | θ = 4.8–65.6° |
α = 91.249 (2)° | µ = 2.22 mm−1 |
β = 113.506 (2)° | T = 173 K |
γ = 110.292 (2)° | Prism, colorless |
V = 626.73 (3) Å3 | 0.50 × 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 Source | 2096 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and φ scans | θmax = 65.6°, θmin = 4.9° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −9→9 |
Tmin = 0.668, Tmax = 1.000 | k = −10→9 |
12480 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H 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 reflections | Δρmax = 0.25 e Å−3 |
172 parameters | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.37970 (5) | 0.74874 (4) | 0.88794 (4) | 0.02876 (15) | |
O1 | 0.28022 (18) | 0.16770 (13) | 0.55060 (13) | 0.0385 (3) | |
N1 | 0.87028 (18) | 1.03625 (15) | 0.77940 (14) | 0.0266 (3) | |
N2 | 0.69580 (18) | 0.98474 (15) | 0.91734 (14) | 0.0236 (3) | |
H2 | 0.680 (3) | 1.026 (2) | 0.9837 (19) | 0.031 (5)* | |
N3 | 0.55882 (18) | 0.76960 (15) | 0.71919 (14) | 0.0244 (3) | |
H3 | 0.648 (3) | 0.821 (2) | 0.701 (2) | 0.040 (5)* | |
C1 | 1.0155 (2) | 1.1378 (2) | 0.75682 (18) | 0.0305 (4) | |
H1 | 1.032837 | 1.102259 | 0.675841 | 0.037* | |
C2 | 1.1401 (2) | 1.29027 (19) | 0.84484 (18) | 0.0303 (4) | |
H2A | 1.240860 | 1.358462 | 0.825316 | 0.036* | |
C3 | 1.1143 (2) | 1.34169 (19) | 0.96316 (18) | 0.0297 (4) | |
H3A | 1.197544 | 1.446526 | 1.025915 | 0.036* | |
C4 | 0.9675 (2) | 1.23997 (19) | 0.98894 (17) | 0.0268 (3) | |
H4 | 0.948182 | 1.272457 | 1.069814 | 0.032* | |
C5 | 0.84737 (19) | 1.08752 (17) | 0.89301 (15) | 0.0215 (3) | |
C6 | 0.5532 (2) | 0.83663 (17) | 0.83584 (15) | 0.0215 (3) | |
C7 | 0.4118 (2) | 0.62124 (18) | 0.61906 (16) | 0.0225 (3) | |
C8 | 0.4249 (2) | 0.46847 (18) | 0.64025 (16) | 0.0239 (3) | |
H8 | 0.528426 | 0.461636 | 0.721088 | 0.029* | |
C9 | 0.2840 (2) | 0.32518 (18) | 0.54118 (16) | 0.0247 (3) | |
C10 | 0.1332 (2) | 0.33607 (19) | 0.42311 (17) | 0.0297 (4) | |
H10 | 0.036818 | 0.238022 | 0.355995 | 0.036* | |
C11 | 0.1238 (2) | 0.4893 (2) | 0.40360 (18) | 0.0349 (4) | |
H11 | 0.020819 | 0.496461 | 0.322431 | 0.042* | |
C12 | 0.2633 (2) | 0.6337 (2) | 0.50136 (18) | 0.0313 (4) | |
H12 | 0.256619 | 0.739342 | 0.487419 | 0.038* | |
C13 | 0.4251 (3) | 0.1471 (2) | 0.6749 (2) | 0.0457 (5) | |
H13A | 0.402596 | 0.028361 | 0.670313 | 0.069* | |
H13B | 0.425443 | 0.190958 | 0.765138 | 0.069* | |
H13C | 0.546803 | 0.207955 | 0.674384 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0302 (2) | 0.0208 (2) | 0.0309 (2) | −0.00158 (16) | 0.01936 (18) | −0.00503 (15) |
O1 | 0.0508 (7) | 0.0212 (6) | 0.0308 (6) | 0.0126 (5) | 0.0071 (5) | −0.0007 (5) |
N1 | 0.0268 (7) | 0.0217 (6) | 0.0297 (7) | 0.0043 (5) | 0.0155 (6) | −0.0001 (5) |
N2 | 0.0258 (6) | 0.0191 (6) | 0.0226 (6) | 0.0028 (5) | 0.0126 (5) | −0.0036 (5) |
N3 | 0.0230 (7) | 0.0203 (6) | 0.0260 (7) | 0.0017 (5) | 0.0131 (5) | −0.0042 (5) |
C1 | 0.0311 (8) | 0.0276 (8) | 0.0350 (9) | 0.0076 (7) | 0.0198 (7) | 0.0035 (7) |
C2 | 0.0268 (8) | 0.0248 (8) | 0.0388 (9) | 0.0057 (6) | 0.0174 (7) | 0.0077 (7) |
C3 | 0.0252 (8) | 0.0206 (7) | 0.0316 (8) | 0.0014 (6) | 0.0076 (7) | −0.0001 (6) |
C4 | 0.0270 (8) | 0.0235 (8) | 0.0246 (8) | 0.0053 (6) | 0.0100 (6) | −0.0012 (6) |
C5 | 0.0210 (7) | 0.0193 (7) | 0.0220 (7) | 0.0070 (6) | 0.0082 (6) | 0.0034 (6) |
C6 | 0.0232 (7) | 0.0165 (7) | 0.0220 (7) | 0.0063 (6) | 0.0087 (6) | 0.0005 (6) |
C7 | 0.0224 (7) | 0.0202 (7) | 0.0232 (7) | 0.0035 (6) | 0.0127 (6) | −0.0041 (6) |
C8 | 0.0257 (8) | 0.0252 (8) | 0.0198 (7) | 0.0088 (6) | 0.0101 (6) | 0.0002 (6) |
C9 | 0.0329 (8) | 0.0196 (7) | 0.0218 (7) | 0.0076 (6) | 0.0145 (6) | −0.0006 (6) |
C10 | 0.0281 (8) | 0.0245 (8) | 0.0253 (8) | 0.0037 (6) | 0.0072 (6) | −0.0058 (6) |
C11 | 0.0292 (8) | 0.0332 (9) | 0.0304 (9) | 0.0116 (7) | 0.0024 (7) | −0.0021 (7) |
C12 | 0.0332 (9) | 0.0240 (8) | 0.0338 (9) | 0.0126 (7) | 0.0107 (7) | 0.0002 (7) |
C13 | 0.0624 (12) | 0.0315 (9) | 0.0382 (10) | 0.0249 (9) | 0.0114 (9) | 0.0076 (8) |
Geometric parameters (Å, º) top
S1—C6 | 1.6910 (15) | C3—C4 | 1.375 (2) |
O1—C9 | 1.3655 (19) | C4—H4 | 0.9500 |
O1—C13 | 1.428 (2) | C4—C5 | 1.398 (2) |
N1—C1 | 1.347 (2) | C7—C8 | 1.386 (2) |
N1—C5 | 1.3303 (19) | C7—C12 | 1.381 (2) |
N2—H2 | 0.833 (17) | C8—H8 | 0.9500 |
N2—C5 | 1.4007 (19) | C8—C9 | 1.392 (2) |
N2—C6 | 1.3689 (19) | C9—C10 | 1.389 (2) |
N3—H3 | 0.828 (17) | C10—H10 | 0.9500 |
N3—C6 | 1.3290 (19) | C10—C11 | 1.377 (2) |
N3—C7 | 1.4352 (18) | C11—H11 | 0.9500 |
C1—H1 | 0.9500 | C11—C12 | 1.390 (2) |
C1—C2 | 1.375 (2) | C12—H12 | 0.9500 |
C2—H2A | 0.9500 | C13—H13A | 0.9800 |
C2—C3 | 1.389 (2) | C13—H13B | 0.9800 |
C3—H3A | 0.9500 | C13—H13C | 0.9800 |
| | | |
C9—O1—C13 | 117.87 (13) | N3—C6—N2 | 117.86 (13) |
C5—N1—C1 | 117.73 (13) | C8—C7—N3 | 119.07 (13) |
C5—N2—H2 | 115.5 (13) | C12—C7—N3 | 119.58 (13) |
C6—N2—H2 | 113.8 (13) | C12—C7—C8 | 121.32 (14) |
C6—N2—C5 | 129.96 (13) | C7—C8—H8 | 120.5 |
C6—N3—H3 | 117.5 (14) | C7—C8—C9 | 118.93 (14) |
C6—N3—C7 | 123.30 (13) | C9—C8—H8 | 120.5 |
C7—N3—H3 | 119.1 (14) | O1—C9—C8 | 124.51 (14) |
N1—C1—H1 | 118.3 | O1—C9—C10 | 115.24 (13) |
N1—C1—C2 | 123.43 (15) | C10—C9—C8 | 120.24 (14) |
C2—C1—H1 | 118.3 | C9—C10—H10 | 120.1 |
C1—C2—H2A | 121.0 | C11—C10—C9 | 119.82 (14) |
C1—C2—C3 | 118.07 (14) | C11—C10—H10 | 120.1 |
C3—C2—H2A | 121.0 | C10—C11—H11 | 119.6 |
C2—C3—H3A | 120.2 | C10—C11—C12 | 120.72 (15) |
C4—C3—C2 | 119.63 (14) | C12—C11—H11 | 119.6 |
C4—C3—H3A | 120.2 | C7—C12—C11 | 118.96 (15) |
C3—C4—H4 | 120.9 | C7—C12—H12 | 120.5 |
C3—C4—C5 | 118.25 (14) | C11—C12—H12 | 120.5 |
C5—C4—H4 | 120.9 | O1—C13—H13A | 109.5 |
N1—C5—N2 | 118.64 (13) | O1—C13—H13B | 109.5 |
N1—C5—C4 | 122.89 (13) | O1—C13—H13C | 109.5 |
C4—C5—N2 | 118.47 (13) | H13A—C13—H13B | 109.5 |
N2—C6—S1 | 118.69 (11) | H13A—C13—H13C | 109.5 |
N3—C6—S1 | 123.46 (11) | H13B—C13—H13C | 109.5 |
| | | |
O1—C9—C10—C11 | −179.94 (15) | C6—N2—C5—C4 | 175.50 (14) |
N1—C1—C2—C3 | 0.0 (2) | C6—N3—C7—C8 | −94.15 (17) |
N3—C7—C8—C9 | −178.66 (13) | C6—N3—C7—C12 | 87.82 (19) |
N3—C7—C12—C11 | 178.71 (14) | C7—N3—C6—S1 | 4.4 (2) |
C1—N1—C5—N2 | 179.20 (13) | C7—N3—C6—N2 | −175.49 (13) |
C1—N1—C5—C4 | −0.5 (2) | C7—C8—C9—O1 | −179.53 (14) |
C1—C2—C3—C4 | 0.2 (2) | C7—C8—C9—C10 | 0.1 (2) |
C2—C3—C4—C5 | −0.6 (2) | C8—C7—C12—C11 | 0.7 (2) |
C3—C4—C5—N1 | 0.7 (2) | C8—C9—C10—C11 | 0.4 (2) |
C3—C4—C5—N2 | −178.94 (13) | C9—C10—C11—C12 | −0.3 (3) |
C5—N1—C1—C2 | 0.1 (2) | C10—C11—C12—C7 | −0.2 (3) |
C5—N2—C6—S1 | −175.35 (12) | C12—C7—C8—C9 | −0.7 (2) |
C5—N2—C6—N3 | 4.6 (2) | C13—O1—C9—C8 | 3.6 (2) |
C6—N2—C5—N1 | −4.2 (2) | C13—O1—C9—C10 | −176.05 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.83 (2) | 2.62 (2) | 3.3882 (13) | 154 (2) |
N3—H3···N1 | 0.83 (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)2 | Dx = 1.679 Mg m−3 |
Mr = 720.19 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 62086 reflections |
a = 18.1534 (4) Å | θ = 2.2–39.5° |
b = 7.1814 (1) Å | µ = 0.98 mm−1 |
c = 21.8523 (4) Å | T = 110 K |
V = 2848.81 (9) Å3 | Prism, green |
Z = 4 | 0.33 × 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 Source | 2703 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω and φ scans | θmax = 25.7°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −22→17 |
Tmin = 0.835, Tmax = 1.000 | k = −8→8 |
72311 measured reflections | l = −26→26 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H 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 reflections | Δρmax = 0.79 e Å−3 |
215 parameters | Δρmin = −0.66 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.500000 | 0.47025 (8) | 0.750000 | 0.01397 (16) | |
S1 | 0.35592 (5) | 0.40264 (13) | 0.58540 (4) | 0.0215 (2) | |
O1 | 0.66894 (15) | 0.2340 (4) | 0.56003 (12) | 0.0299 (6) | |
O2 | 0.500000 | 0.1889 (5) | 0.750000 | 0.0364 (10) | |
H2A | 0.5393 (11) | 0.1272 (12) | 0.759 (3) | 0.055* | 0.5 |
H2B | 0.468 (2) | 0.1274 (12) | 0.729 (2) | 0.055* | 0.5 |
N1 | 0.41384 (14) | 0.6490 (4) | 0.77375 (12) | 0.0149 (6) | |
N2 | 0.33369 (15) | 0.5337 (4) | 0.69802 (13) | 0.0179 (6) | |
H2 | 0.2892 (12) | 0.525 (6) | 0.6845 (16) | 0.021* | |
N3 | 0.45591 (15) | 0.4536 (4) | 0.66819 (12) | 0.0145 (6) | |
C1 | 0.42390 (19) | 0.7627 (5) | 0.82261 (15) | 0.0190 (7) | |
H1 | 0.472590 | 0.782092 | 0.837217 | 0.023* | |
C2 | 0.3669 (2) | 0.8512 (5) | 0.85188 (16) | 0.0238 (8) | |
H2C | 0.375935 | 0.931356 | 0.885621 | 0.029* | |
C3 | 0.2957 (2) | 0.8207 (5) | 0.83105 (16) | 0.0245 (8) | |
H3 | 0.255062 | 0.873649 | 0.852165 | 0.029* | |
C4 | 0.28424 (18) | 0.7144 (5) | 0.78011 (16) | 0.0204 (7) | |
H4 | 0.236004 | 0.695842 | 0.764397 | 0.024* | |
C5 | 0.34564 (18) | 0.6334 (4) | 0.75162 (15) | 0.0166 (7) | |
C6 | 0.38493 (18) | 0.4711 (5) | 0.65788 (14) | 0.0159 (7) | |
C7 | 0.49227 (19) | 0.3806 (4) | 0.61717 (15) | 0.0179 (7) | |
C8 | 0.5671 (2) | 0.3422 (5) | 0.61330 (15) | 0.0209 (7) | |
H8 | 0.598738 | 0.364950 | 0.647094 | 0.025* | |
C9 | 0.5946 (2) | 0.2700 (5) | 0.55917 (16) | 0.0229 (8) | |
C10 | 0.5492 (2) | 0.2336 (5) | 0.50918 (16) | 0.0248 (8) | |
H10 | 0.569235 | 0.183235 | 0.472601 | 0.030* | |
C11 | 0.4744 (2) | 0.2715 (5) | 0.51330 (16) | 0.0246 (8) | |
H11 | 0.442796 | 0.248001 | 0.479545 | 0.030* | |
C12 | 0.44650 (19) | 0.3441 (5) | 0.56721 (15) | 0.0199 (7) | |
C13 | 0.7001 (2) | 0.1407 (6) | 0.50876 (18) | 0.0347 (10) | |
H13A | 0.696266 | 0.220385 | 0.472504 | 0.052* | |
H13B | 0.673452 | 0.024068 | 0.501516 | 0.052* | |
H13C | 0.752063 | 0.113305 | 0.516961 | 0.052* | |
O3 | 0.36773 (14) | 0.0698 (4) | 0.70721 (12) | 0.0281 (6) | |
O4 | 0.29737 (14) | −0.0570 (4) | 0.63928 (12) | 0.0302 (6) | |
O5 | 0.41492 (14) | −0.0873 (4) | 0.63256 (13) | 0.0340 (7) | |
N4 | 0.36037 (15) | −0.0238 (4) | 0.65980 (13) | 0.0197 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0135 (3) | 0.0163 (3) | 0.0122 (3) | 0.000 | −0.0014 (2) | 0.000 |
S1 | 0.0219 (4) | 0.0260 (5) | 0.0168 (4) | −0.0031 (4) | −0.0056 (3) | 0.0002 (3) |
O1 | 0.0295 (14) | 0.0349 (15) | 0.0252 (13) | 0.0057 (12) | 0.0083 (11) | −0.0043 (12) |
O2 | 0.046 (3) | 0.0155 (18) | 0.048 (2) | 0.000 | −0.033 (2) | 0.000 |
N1 | 0.0120 (13) | 0.0151 (13) | 0.0177 (13) | 0.0017 (11) | 0.0007 (10) | 0.0004 (11) |
N2 | 0.0121 (13) | 0.0196 (15) | 0.0218 (14) | −0.0023 (11) | −0.0011 (11) | 0.0020 (12) |
N3 | 0.0183 (14) | 0.0141 (14) | 0.0112 (12) | −0.0012 (11) | 0.0000 (10) | 0.0014 (11) |
C1 | 0.0197 (17) | 0.0173 (16) | 0.0200 (16) | 0.0001 (13) | −0.0019 (13) | −0.0021 (14) |
C2 | 0.032 (2) | 0.0183 (18) | 0.0214 (17) | 0.0021 (15) | 0.0020 (15) | −0.0016 (14) |
C3 | 0.0248 (18) | 0.0224 (18) | 0.0264 (18) | 0.0071 (15) | 0.0091 (15) | 0.0028 (15) |
C4 | 0.0143 (16) | 0.0193 (17) | 0.0276 (18) | 0.0011 (13) | 0.0016 (14) | 0.0063 (15) |
C5 | 0.0180 (16) | 0.0117 (15) | 0.0202 (16) | −0.0021 (12) | 0.0008 (13) | 0.0037 (13) |
C6 | 0.0215 (16) | 0.0136 (16) | 0.0127 (15) | −0.0039 (13) | −0.0017 (13) | 0.0024 (13) |
C7 | 0.0266 (18) | 0.0109 (15) | 0.0162 (15) | −0.0008 (14) | 0.0011 (13) | 0.0016 (12) |
C8 | 0.0248 (18) | 0.0191 (17) | 0.0189 (16) | −0.0013 (15) | 0.0002 (14) | −0.0018 (14) |
C9 | 0.0259 (18) | 0.0180 (17) | 0.0249 (18) | 0.0003 (15) | 0.0053 (15) | 0.0007 (15) |
C10 | 0.038 (2) | 0.0168 (17) | 0.0194 (18) | −0.0019 (16) | 0.0061 (15) | −0.0022 (14) |
C11 | 0.038 (2) | 0.0204 (18) | 0.0155 (17) | −0.0066 (16) | −0.0015 (15) | 0.0000 (14) |
C12 | 0.0251 (18) | 0.0169 (16) | 0.0178 (16) | −0.0037 (14) | 0.0003 (14) | 0.0029 (14) |
C13 | 0.040 (2) | 0.036 (2) | 0.028 (2) | 0.0104 (19) | 0.0169 (17) | −0.0028 (18) |
O3 | 0.0310 (14) | 0.0261 (14) | 0.0272 (13) | −0.0052 (11) | 0.0005 (11) | −0.0018 (12) |
O4 | 0.0180 (13) | 0.0412 (17) | 0.0314 (14) | −0.0043 (12) | −0.0017 (11) | −0.0054 (13) |
O5 | 0.0202 (13) | 0.0452 (17) | 0.0367 (15) | 0.0088 (13) | 0.0059 (11) | 0.0007 (14) |
N4 | 0.0165 (14) | 0.0191 (15) | 0.0234 (15) | −0.0001 (12) | 0.0011 (12) | 0.0047 (12) |
Geometric parameters (Å, º) top
Cu1—O2 | 2.020 (4) | C2—H2C | 0.9500 |
Cu1—N1i | 2.089 (3) | C2—C3 | 1.387 (5) |
Cu1—N1 | 2.089 (3) | C3—H3 | 0.9500 |
Cu1—N3i | 1.962 (3) | C3—C4 | 1.366 (5) |
Cu1—N3 | 1.962 (3) | C4—H4 | 0.9500 |
S1—C6 | 1.740 (3) | C4—C5 | 1.403 (5) |
S1—C12 | 1.743 (4) | C7—C8 | 1.388 (5) |
O1—C9 | 1.374 (4) | C7—C12 | 1.397 (5) |
O1—C13 | 1.423 (4) | C8—H8 | 0.9500 |
O2—H2Ai | 0.861 (7) | C8—C9 | 1.385 (5) |
O2—H2A | 0.861 (14) | C9—C10 | 1.393 (5) |
O2—H2Bi | 0.861 (7) | C10—H10 | 0.9500 |
O2—H2B | 0.861 (14) | C10—C11 | 1.387 (5) |
N1—C1 | 1.357 (4) | C11—H11 | 0.9500 |
N1—C5 | 1.334 (4) | C11—C12 | 1.384 (5) |
N2—H2 | 0.861 (18) | C13—H13A | 0.9800 |
N2—C5 | 1.390 (4) | C13—H13B | 0.9800 |
N2—C6 | 1.355 (4) | C13—H13C | 0.9800 |
N3—C6 | 1.314 (4) | O3—N4 | 1.242 (4) |
N3—C7 | 1.398 (4) | O4—N4 | 1.251 (4) |
C1—H1 | 0.9500 | O5—N4 | 1.242 (4) |
C1—C2 | 1.372 (5) | | |
| | | |
O2—Cu1—N1 | 127.91 (8) | C4—C3—H3 | 120.1 |
O2—Cu1—N1i | 127.91 (7) | C3—C4—H4 | 120.9 |
N1i—Cu1—N1 | 104.18 (15) | C3—C4—C5 | 118.2 (3) |
N3—Cu1—O2 | 86.51 (8) | C5—C4—H4 | 120.9 |
N3i—Cu1—O2 | 86.51 (8) | N1—C5—N2 | 119.6 (3) |
N3—Cu1—N1 | 87.61 (11) | N1—C5—C4 | 122.8 (3) |
N3—Cu1—N1i | 96.69 (11) | N2—C5—C4 | 117.6 (3) |
N3i—Cu1—N1i | 87.61 (11) | N2—C6—S1 | 118.4 (2) |
N3i—Cu1—N1 | 96.69 (11) | N3—C6—S1 | 115.2 (2) |
N3—Cu1—N3i | 173.03 (16) | N3—C6—N2 | 126.4 (3) |
C6—S1—C12 | 89.44 (16) | C8—C7—N3 | 125.8 (3) |
C9—O1—C13 | 117.9 (3) | C8—C7—C12 | 119.8 (3) |
Cu1—O2—H2A | 121.0 | C12—C7—N3 | 114.4 (3) |
Cu1—O2—H2Ai | 121.0 (8) | C7—C8—H8 | 120.7 |
Cu1—O2—H2B | 120.9 | C9—C8—C7 | 118.6 (3) |
Cu1—O2—H2Bi | 120.9 (8) | C9—C8—H8 | 120.7 |
H2A—O2—H2Ai | 118.0 | O1—C9—C8 | 114.4 (3) |
H2A—O2—H2B | 114.6 | O1—C9—C10 | 123.8 (3) |
H2Ai—O2—H2Bi | 114.6 | C8—C9—C10 | 121.8 (3) |
H2B—O2—H2Bi | 118.2 | C9—C10—H10 | 120.3 |
C1—N1—Cu1 | 117.7 (2) | C11—C10—C9 | 119.4 (3) |
C5—N1—Cu1 | 123.6 (2) | C11—C10—H10 | 120.3 |
C5—N1—C1 | 117.4 (3) | C10—C11—H11 | 120.4 |
C5—N2—H2 | 118 (3) | C12—C11—C10 | 119.2 (3) |
C6—N2—H2 | 113 (3) | C12—C11—H11 | 120.4 |
C6—N2—C5 | 127.5 (3) | C7—C12—S1 | 109.7 (3) |
C6—N3—Cu1 | 123.4 (2) | C11—C12—S1 | 129.1 (3) |
C6—N3—C7 | 111.2 (3) | C11—C12—C7 | 121.2 (3) |
C7—N3—Cu1 | 123.8 (2) | O1—C13—H13A | 109.5 |
N1—C1—H1 | 118.5 | O1—C13—H13B | 109.5 |
N1—C1—C2 | 122.9 (3) | O1—C13—H13C | 109.5 |
C2—C1—H1 | 118.5 | H13A—C13—H13B | 109.5 |
C1—C2—H2C | 120.8 | H13A—C13—H13C | 109.5 |
C1—C2—C3 | 118.5 (3) | H13B—C13—H13C | 109.5 |
C3—C2—H2C | 120.8 | O3—N4—O4 | 120.0 (3) |
C2—C3—H3 | 120.1 | O3—N4—O5 | 120.8 (3) |
C4—C3—C2 | 119.9 (3) | O5—N4—O4 | 119.1 (3) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2B···O3 | 0.86 | 1.92 | 2.715 (3) | 151 (3) |
O2—H2A···O3i | 0.86 | 1.89 | 2.715 (3) | 160 |
N2—H2···O4ii | 0.86 (2) | 1.95 (2) | 2.781 (4) | 162 (4) |
C1—H1···O5iii | 0.95 | 2.34 | 3.268 (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·H2O | Z = 2 |
Mr = 837.96 | F(000) = 820 |
Triclinic, P1 | Dx = 1.907 Mg m−3 |
a = 10.0052 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5940 (2) Å | Cell parameters from 104589 reflections |
c = 12.9412 (1) Å | θ = 2.0–50.4° |
α = 111.867 (1)° | µ = 5.50 mm−1 |
β = 97.271 (1)° | T = 110 K |
γ = 99.755 (1)° | Prism, colorless |
V = 1459.03 (3) Å3 | 0.31 × 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 Source | 5961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω and φ scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −12→12 |
Tmin = 0.473, Tmax = 1.000 | k = −15→15 |
85384 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.018 | H 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 reflections | Δρmax = 0.76 e Å−3 |
396 parameters | Δρmin = −0.85 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S2 | 0.41939 (6) | 0.75769 (5) | 0.72552 (5) | 0.01731 (12) | |
O2 | 0.69431 (19) | 0.54362 (16) | 0.99756 (15) | 0.0200 (4) | |
N4 | 0.6790 (2) | 0.59876 (18) | 0.46614 (18) | 0.0151 (4) | |
H4 | 0.685 (3) | 0.588 (3) | 0.524 (2) | 0.026 (9)* | |
N5 | 0.5244 (2) | 0.71619 (19) | 0.53596 (18) | 0.0166 (4) | |
H5 | 0.475 (3) | 0.762 (2) | 0.527 (3) | 0.030 (9)* | |
N6 | 0.6055 (2) | 0.63748 (18) | 0.66463 (17) | 0.0162 (4) | |
C14 | 0.7519 (3) | 0.5493 (2) | 0.3865 (2) | 0.0188 (5) | |
H14 | 0.809858 | 0.500715 | 0.398392 | 0.023* | |
C15 | 0.7421 (3) | 0.5692 (2) | 0.2899 (2) | 0.0203 (5) | |
H15 | 0.792297 | 0.534357 | 0.233677 | 0.024* | |
C16 | 0.6570 (3) | 0.6418 (2) | 0.2745 (2) | 0.0192 (5) | |
H16 | 0.650252 | 0.657322 | 0.207853 | 0.023* | |
C17 | 0.5831 (3) | 0.6909 (2) | 0.3550 (2) | 0.0176 (5) | |
H17 | 0.524868 | 0.739685 | 0.344054 | 0.021* | |
C18 | 0.5944 (2) | 0.6682 (2) | 0.4532 (2) | 0.0147 (5) | |
C19 | 0.5267 (2) | 0.6976 (2) | 0.6343 (2) | 0.0151 (5) | |
C20 | 0.5867 (2) | 0.6376 (2) | 0.7700 (2) | 0.0154 (5) | |
C21 | 0.6560 (2) | 0.5815 (2) | 0.8265 (2) | 0.0158 (5) | |
H21 | 0.719188 | 0.537189 | 0.793601 | 0.019* | |
C22 | 0.6301 (2) | 0.5923 (2) | 0.9322 (2) | 0.0162 (5) | |
C23 | 0.5347 (3) | 0.6558 (2) | 0.9798 (2) | 0.0169 (5) | |
H23 | 0.518375 | 0.661493 | 1.052217 | 0.020* | |
C24 | 0.4644 (3) | 0.7100 (2) | 0.9233 (2) | 0.0180 (5) | |
H24 | 0.399545 | 0.752526 | 0.955570 | 0.022* | |
C25 | 0.4912 (2) | 0.7005 (2) | 0.8175 (2) | 0.0149 (5) | |
C26 | 0.7772 (3) | 0.4653 (3) | 0.9462 (2) | 0.0249 (6) | |
H26A | 0.721112 | 0.401457 | 0.875988 | 0.037* | |
H26B | 0.811827 | 0.432201 | 0.998916 | 0.037* | |
H26C | 0.855757 | 0.508348 | 0.928260 | 0.037* | |
S1 | 0.67232 (6) | 1.00715 (5) | 0.96345 (5) | 0.01600 (12) | |
O1 | 0.93392 (19) | 0.79817 (16) | 1.24720 (14) | 0.0197 (4) | |
N1 | 0.9505 (2) | 0.85301 (18) | 0.71852 (18) | 0.0162 (4) | |
H1 | 0.960 (3) | 0.849 (3) | 0.779 (2) | 0.025 (8)* | |
N2 | 0.7788 (2) | 0.95630 (18) | 0.77372 (17) | 0.0158 (4) | |
H2 | 0.723 (3) | 0.993 (3) | 0.755 (3) | 0.041 (10)* | |
N3 | 0.8627 (2) | 0.88981 (18) | 0.91125 (17) | 0.0149 (4) | |
C1 | 1.0317 (3) | 0.8078 (2) | 0.6446 (2) | 0.0195 (5) | |
H1A | 1.097152 | 0.768019 | 0.663529 | 0.023* | |
C2 | 1.0195 (3) | 0.8194 (2) | 0.5435 (2) | 0.0219 (5) | |
H2A | 1.075907 | 0.787838 | 0.491432 | 0.026* | |
C3 | 0.9224 (3) | 0.8786 (2) | 0.5176 (2) | 0.0204 (5) | |
H3 | 0.911822 | 0.886335 | 0.446918 | 0.024* | |
C4 | 0.8424 (3) | 0.9256 (2) | 0.5936 (2) | 0.0182 (5) | |
H4A | 0.777686 | 0.966903 | 0.576547 | 0.022* | |
C5 | 0.8574 (2) | 0.9118 (2) | 0.6971 (2) | 0.0155 (5) | |
C6 | 0.7823 (2) | 0.9451 (2) | 0.8760 (2) | 0.0140 (5) | |
C7 | 0.8413 (2) | 0.8923 (2) | 1.0163 (2) | 0.0143 (5) | |
C8 | 0.9101 (2) | 0.8387 (2) | 1.0766 (2) | 0.0148 (5) | |
H8 | 0.978627 | 0.798434 | 1.048471 | 0.018* | |
C9 | 0.8748 (3) | 0.8464 (2) | 1.1788 (2) | 0.0161 (5) | |
C10 | 0.7728 (3) | 0.9049 (2) | 1.2202 (2) | 0.0177 (5) | |
H10 | 0.750185 | 0.907910 | 1.290212 | 0.021* | |
C11 | 0.7047 (3) | 0.9584 (2) | 1.1609 (2) | 0.0179 (5) | |
H11 | 0.635812 | 0.998071 | 1.189050 | 0.021* | |
C12 | 0.7408 (2) | 0.9520 (2) | 1.0584 (2) | 0.0146 (5) | |
C13 | 1.0300 (3) | 0.7290 (2) | 1.2054 (2) | 0.0228 (5) | |
H13A | 0.984946 | 0.664647 | 1.131747 | 0.034* | |
H13B | 1.060746 | 0.696365 | 1.259637 | 0.034* | |
H13C | 1.110250 | 0.778632 | 1.196026 | 0.034* | |
Au1 | 0.95986 (2) | 0.55935 (2) | 0.71308 (2) | 0.01682 (3) | |
Cl1 | 1.11166 (7) | 0.70866 (6) | 0.86031 (6) | 0.02465 (13) | |
Cl2 | 0.80710 (7) | 0.41058 (6) | 0.56663 (6) | 0.02767 (14) | |
O3 | 0.3768 (2) | 0.87843 (19) | 0.5227 (2) | 0.0272 (4) | |
H3A | 0.425 (4) | 0.938 (3) | 0.566 (3) | 0.037 (11)* | |
H3B | 0.380 (4) | 0.885 (4) | 0.465 (3) | 0.053 (13)* | |
Cl3 | 0.58921 (7) | 1.10213 (6) | 0.71166 (6) | 0.02530 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S2 | 0.0189 (3) | 0.0197 (3) | 0.0165 (3) | 0.0097 (2) | 0.0050 (2) | 0.0082 (2) |
O2 | 0.0229 (9) | 0.0241 (9) | 0.0196 (9) | 0.0095 (8) | 0.0066 (7) | 0.0135 (8) |
N4 | 0.0166 (10) | 0.0163 (10) | 0.0163 (10) | 0.0052 (8) | 0.0042 (8) | 0.0099 (8) |
N5 | 0.0184 (10) | 0.0189 (10) | 0.0182 (10) | 0.0090 (8) | 0.0051 (8) | 0.0113 (9) |
N6 | 0.0172 (10) | 0.0193 (10) | 0.0150 (10) | 0.0059 (8) | 0.0044 (8) | 0.0091 (8) |
C14 | 0.0179 (12) | 0.0181 (12) | 0.0214 (13) | 0.0056 (10) | 0.0050 (10) | 0.0080 (10) |
C15 | 0.0219 (13) | 0.0198 (12) | 0.0187 (12) | 0.0054 (10) | 0.0069 (10) | 0.0061 (10) |
C16 | 0.0213 (13) | 0.0181 (12) | 0.0168 (12) | 0.0013 (10) | 0.0019 (10) | 0.0074 (10) |
C17 | 0.0189 (12) | 0.0182 (12) | 0.0170 (12) | 0.0045 (10) | 0.0012 (10) | 0.0093 (10) |
C18 | 0.0133 (11) | 0.0129 (11) | 0.0173 (12) | 0.0018 (9) | 0.0022 (9) | 0.0064 (9) |
C19 | 0.0142 (11) | 0.0149 (11) | 0.0175 (12) | 0.0036 (9) | 0.0033 (9) | 0.0080 (10) |
C20 | 0.0142 (11) | 0.0154 (11) | 0.0151 (11) | 0.0001 (9) | 0.0018 (9) | 0.0063 (9) |
C21 | 0.0146 (11) | 0.0182 (12) | 0.0180 (12) | 0.0049 (9) | 0.0047 (9) | 0.0104 (10) |
C22 | 0.0153 (11) | 0.0149 (11) | 0.0187 (12) | 0.0005 (9) | 0.0016 (9) | 0.0089 (10) |
C23 | 0.0167 (12) | 0.0183 (12) | 0.0150 (11) | 0.0018 (9) | 0.0043 (9) | 0.0066 (10) |
C24 | 0.0172 (12) | 0.0188 (12) | 0.0178 (12) | 0.0046 (10) | 0.0054 (10) | 0.0064 (10) |
C25 | 0.0137 (11) | 0.0140 (11) | 0.0173 (12) | 0.0035 (9) | 0.0024 (9) | 0.0068 (9) |
C26 | 0.0271 (14) | 0.0308 (15) | 0.0249 (14) | 0.0147 (12) | 0.0070 (11) | 0.0162 (12) |
S1 | 0.0184 (3) | 0.0168 (3) | 0.0156 (3) | 0.0082 (2) | 0.0054 (2) | 0.0073 (2) |
O1 | 0.0275 (10) | 0.0230 (9) | 0.0139 (8) | 0.0104 (8) | 0.0053 (7) | 0.0108 (7) |
N1 | 0.0191 (10) | 0.0169 (10) | 0.0148 (10) | 0.0046 (8) | 0.0040 (8) | 0.0086 (9) |
N2 | 0.0180 (10) | 0.0185 (10) | 0.0160 (10) | 0.0078 (8) | 0.0051 (8) | 0.0104 (8) |
N3 | 0.0169 (10) | 0.0155 (10) | 0.0144 (10) | 0.0039 (8) | 0.0041 (8) | 0.0081 (8) |
C1 | 0.0207 (13) | 0.0183 (12) | 0.0217 (13) | 0.0058 (10) | 0.0083 (10) | 0.0088 (10) |
C2 | 0.0269 (14) | 0.0206 (13) | 0.0181 (12) | 0.0048 (11) | 0.0099 (11) | 0.0065 (10) |
C3 | 0.0241 (13) | 0.0212 (13) | 0.0149 (12) | −0.0002 (10) | 0.0039 (10) | 0.0087 (10) |
C4 | 0.0195 (12) | 0.0189 (12) | 0.0172 (12) | 0.0030 (10) | 0.0019 (10) | 0.0095 (10) |
C5 | 0.0159 (11) | 0.0140 (11) | 0.0153 (11) | 0.0004 (9) | 0.0017 (9) | 0.0061 (9) |
C6 | 0.0124 (11) | 0.0136 (11) | 0.0154 (11) | 0.0016 (9) | 0.0030 (9) | 0.0060 (9) |
C7 | 0.0150 (11) | 0.0135 (11) | 0.0122 (11) | 0.0005 (9) | 0.0021 (9) | 0.0040 (9) |
C8 | 0.0158 (11) | 0.0154 (11) | 0.0153 (11) | 0.0048 (9) | 0.0046 (9) | 0.0076 (9) |
C9 | 0.0182 (12) | 0.0146 (11) | 0.0147 (11) | 0.0021 (9) | 0.0015 (9) | 0.0063 (9) |
C10 | 0.0218 (13) | 0.0179 (12) | 0.0130 (11) | 0.0036 (10) | 0.0066 (10) | 0.0053 (10) |
C11 | 0.0197 (12) | 0.0161 (12) | 0.0167 (12) | 0.0053 (10) | 0.0059 (10) | 0.0043 (10) |
C12 | 0.0156 (11) | 0.0122 (11) | 0.0145 (11) | 0.0025 (9) | 0.0017 (9) | 0.0044 (9) |
C13 | 0.0249 (13) | 0.0271 (14) | 0.0240 (13) | 0.0124 (11) | 0.0062 (11) | 0.0158 (11) |
Au1 | 0.01572 (5) | 0.01910 (5) | 0.01926 (5) | 0.00721 (4) | 0.00532 (4) | 0.00985 (4) |
Cl1 | 0.0202 (3) | 0.0280 (3) | 0.0226 (3) | 0.0066 (3) | 0.0017 (2) | 0.0073 (3) |
Cl2 | 0.0290 (3) | 0.0211 (3) | 0.0284 (3) | 0.0057 (3) | −0.0016 (3) | 0.0074 (3) |
O3 | 0.0301 (11) | 0.0249 (11) | 0.0333 (12) | 0.0103 (9) | 0.0100 (10) | 0.0163 (10) |
Cl3 | 0.0242 (3) | 0.0298 (3) | 0.0319 (3) | 0.0131 (3) | 0.0070 (3) | 0.0202 (3) |
Geometric parameters (Å, º) top
S2—C19 | 1.747 (2) | O1—C9 | 1.376 (3) |
S2—C25 | 1.746 (2) | O1—C13 | 1.428 (3) |
O2—C22 | 1.373 (3) | N1—H1 | 0.80 (3) |
O2—C26 | 1.426 (3) | N1—C1 | 1.359 (3) |
N4—H4 | 0.81 (3) | N1—C5 | 1.347 (3) |
N4—C14 | 1.360 (3) | N2—H2 | 0.852 (15) |
N4—C18 | 1.354 (3) | N2—C5 | 1.360 (3) |
N5—H5 | 0.851 (15) | N2—C6 | 1.379 (3) |
N5—C18 | 1.361 (3) | N3—C6 | 1.294 (3) |
N5—C19 | 1.375 (3) | N3—C7 | 1.393 (3) |
N6—C19 | 1.301 (3) | C1—H1A | 0.9500 |
N6—C20 | 1.400 (3) | C1—C2 | 1.363 (4) |
C14—H14 | 0.9500 | C2—H2A | 0.9500 |
C14—C15 | 1.358 (4) | C2—C3 | 1.401 (4) |
C15—H15 | 0.9500 | C3—H3 | 0.9500 |
C15—C16 | 1.400 (4) | C3—C4 | 1.373 (4) |
C16—H16 | 0.9500 | C4—H4A | 0.9500 |
C16—C17 | 1.372 (4) | C4—C5 | 1.406 (3) |
C17—H17 | 0.9500 | C7—C8 | 1.397 (3) |
C17—C18 | 1.398 (3) | C7—C12 | 1.401 (3) |
C20—C21 | 1.392 (3) | C8—H8 | 0.9500 |
C20—C25 | 1.400 (3) | C8—C9 | 1.385 (3) |
C21—H21 | 0.9500 | C9—C10 | 1.404 (3) |
C21—C22 | 1.386 (3) | C10—H10 | 0.9500 |
C22—C23 | 1.403 (3) | C10—C11 | 1.383 (4) |
C23—H23 | 0.9500 | C11—H11 | 0.9500 |
C23—C24 | 1.378 (4) | C11—C12 | 1.396 (3) |
C24—H24 | 0.9500 | C13—H13A | 0.9800 |
C24—C25 | 1.394 (3) | C13—H13B | 0.9800 |
C26—H26A | 0.9800 | C13—H13C | 0.9800 |
C26—H26B | 0.9800 | Au1—Cl1 | 2.2592 (7) |
C26—H26C | 0.9800 | Au1—Cl2 | 2.2560 (7) |
S1—C6 | 1.747 (2) | O3—H3A | 0.78 (3) |
S1—C12 | 1.745 (2) | O3—H3B | 0.78 (3) |
| | | |
C25—S2—C19 | 88.15 (11) | C9—O1—C13 | 117.33 (19) |
C22—O2—C26 | 117.14 (19) | C1—N1—H1 | 120 (2) |
C14—N4—H4 | 121 (2) | C5—N1—H1 | 117 (2) |
C18—N4—H4 | 117 (2) | C5—N1—C1 | 122.5 (2) |
C18—N4—C14 | 122.3 (2) | C5—N2—H2 | 115 (2) |
C18—N5—H5 | 118 (2) | C5—N2—C6 | 125.4 (2) |
C18—N5—C19 | 125.7 (2) | C6—N2—H2 | 119 (2) |
C19—N5—H5 | 117 (2) | C6—N3—C7 | 110.1 (2) |
C19—N6—C20 | 109.9 (2) | N1—C1—H1A | 119.9 |
N4—C14—H14 | 119.9 | N1—C1—C2 | 120.3 (2) |
C15—C14—N4 | 120.2 (2) | C2—C1—H1A | 119.9 |
C15—C14—H14 | 119.9 | C1—C2—H2A | 120.6 |
C14—C15—H15 | 120.6 | C1—C2—C3 | 118.8 (2) |
C14—C15—C16 | 118.9 (2) | C3—C2—H2A | 120.6 |
C16—C15—H15 | 120.6 | C2—C3—H3 | 119.8 |
C15—C16—H16 | 119.7 | C4—C3—C2 | 120.5 (2) |
C17—C16—C15 | 120.6 (2) | C4—C3—H3 | 119.8 |
C17—C16—H16 | 119.7 | C3—C4—H4A | 120.4 |
C16—C17—H17 | 120.4 | C3—C4—C5 | 119.2 (2) |
C16—C17—C18 | 119.3 (2) | C5—C4—H4A | 120.4 |
C18—C17—H17 | 120.4 | N1—C5—N2 | 120.6 (2) |
N4—C18—N5 | 119.9 (2) | N1—C5—C4 | 118.7 (2) |
N4—C18—C17 | 118.7 (2) | N2—C5—C4 | 120.6 (2) |
N5—C18—C17 | 121.3 (2) | N2—C6—S1 | 119.11 (18) |
N5—C19—S2 | 119.11 (18) | N3—C6—S1 | 117.41 (18) |
N6—C19—S2 | 117.11 (18) | N3—C6—N2 | 123.5 (2) |
N6—C19—N5 | 123.8 (2) | N3—C7—C8 | 124.4 (2) |
N6—C20—C25 | 114.7 (2) | N3—C7—C12 | 114.6 (2) |
C21—C20—N6 | 124.3 (2) | C8—C7—C12 | 121.0 (2) |
C21—C20—C25 | 120.9 (2) | C7—C8—H8 | 121.2 |
C20—C21—H21 | 121.0 | C9—C8—C7 | 117.5 (2) |
C22—C21—C20 | 117.9 (2) | C9—C8—H8 | 121.2 |
C22—C21—H21 | 121.0 | O1—C9—C8 | 124.0 (2) |
O2—C22—C21 | 123.5 (2) | O1—C9—C10 | 114.6 (2) |
O2—C22—C23 | 115.5 (2) | C8—C9—C10 | 121.5 (2) |
C21—C22—C23 | 121.0 (2) | C9—C10—H10 | 119.4 |
C22—C23—H23 | 119.4 | C11—C10—C9 | 121.2 (2) |
C24—C23—C22 | 121.2 (2) | C11—C10—H10 | 119.4 |
C24—C23—H23 | 119.4 | C10—C11—H11 | 121.1 |
C23—C24—H24 | 121.0 | C10—C11—C12 | 117.7 (2) |
C23—C24—C25 | 118.1 (2) | C12—C11—H11 | 121.1 |
C25—C24—H24 | 121.0 | C7—C12—S1 | 110.12 (17) |
C20—C25—S2 | 110.04 (18) | C11—C12—S1 | 128.73 (19) |
C24—C25—S2 | 129.11 (19) | C11—C12—C7 | 121.1 (2) |
C24—C25—C20 | 120.9 (2) | O1—C13—H13A | 109.5 |
O2—C26—H26A | 109.5 | O1—C13—H13B | 109.5 |
O2—C26—H26B | 109.5 | O1—C13—H13C | 109.5 |
O2—C26—H26C | 109.5 | H13A—C13—H13B | 109.5 |
H26A—C26—H26B | 109.5 | H13A—C13—H13C | 109.5 |
H26A—C26—H26C | 109.5 | H13B—C13—H13C | 109.5 |
H26B—C26—H26C | 109.5 | Cl2—Au1—Cl1 | 179.62 (3) |
C12—S1—C6 | 87.80 (11) | H3A—O3—H3B | 102 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O3 | 0.85 (2) | 1.91 (2) | 2.758 (3) | 173 (3) |
N2—H2···Cl3 | 0.85 (2) | 2.23 (2) | 3.084 (2) | 176 (4) |
C3—H3···O1i | 0.95 | 2.46 | 3.284 (3) | 145 |
O3—H3A···Cl3 | 0.78 (3) | 2.39 (3) | 3.155 (2) | 171 (4) |
O3—H3B···Cl3ii | 0.78 (3) | 2.41 (3) | 3.188 (2) | 174 (4) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z+1. |
Selected short intermolecular interactions for
(HBL1)2[AuCl2]Cl.H2O,
(II) topCg1 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. |
Centroids | Cg···Cg (Å) | Dihedral Angle between Planes (°) |
Cg1···Cg3 | 3.8422 (14) | 6.43 (8) |
Cg2···Cg4 | 3.7491 (14) | 3.38 (8) |
Cg1—Cg2i | 3.8172 (14) | 3.92 (8) |
Cg3···Cg4ii | 3.7667 (14) | 3.00 (8) |
Symmetry codes: (i) -x+2, -y+2, -z+2;
(ii) -x+1, -y+1, -z+1. |
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