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The cationic pseudo-square-planar complex tetra­kis­(1-methyl-2,3-di­hydro-1H-imidazole-2-thione-κS)gold(III) trichloride sesquihydrate, [Au(C4H6N2S)4]Cl3·1.5H2O, was isolated as dark-red crystals from the reaction of chloro­auric acid trihydrate (HAuCl4·3H2O) with four equivalents of methimazole in methanol. The AuIII atoms reside at the corners of the unit cell on an inversion center and are bound by the S atoms of four methimazole ligands in a planar arrangement, with S—Au—S bond angles of approximately 90°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961500474X/ly3007sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961500474X/ly3007Isup2.hkl
Contains datablock I

CCDC reference: 1052635

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010) and Marvinsketch (ChemAxon, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Tetrakis(1-methyl-2,3-dihydro-1H-imidazole-2-thione-κS)gold(III) trichloride sesquihydrate top
Crystal data top
[Au(C4H6N2S)4]Cl3·1.5H2OZ = 1
Mr = 787.05F(000) = 385.00
Triclinic, P1Dx = 1.739 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 8.153 (11) ÅCell parameters from 2388 reflections
b = 9.866 (12) Åθ = 2.7–27.5°
c = 9.969 (12) ŵ = 5.49 mm1
α = 90.179 (12)°T = 173 K
β = 96.892 (14)°Prism, red
γ = 109.15 (2)°0.19 × 0.10 × 0.08 mm
V = 751.3 (17) Å3
Data collection top
Rigaku XtaLAB mini
diffractometer
3254 reflections with F2 > 2σ(F2)
Detector resolution: 6.827 pixels mm-1Rint = 0.041
ω scansθmax = 27.6°
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)
h = 1010
Tmin = 0.491, Tmax = 0.645k = 1212
7972 measured reflectionsl = 1212
3439 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.9654P]
where P = (Fo2 + 2Fc2)/3
3439 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 1.49 e Å3
0 restraintsΔρmin = 1.74 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Au11.00001.00001.00000.03430 (12)
Cl10.6005 (11)0.4011 (10)0.4594 (8)0.0516 (15)0.5000
Cl21.5118 (10)0.8495 (9)0.9627 (8)0.0515 (14)0.5000
Cl30.5192 (5)0.8748 (6)0.6579 (5)0.0674 (12)0.5000
S11.0128 (3)0.92339 (17)0.77963 (15)0.0506 (5)
S20.9997 (3)0.77422 (16)1.07689 (15)0.0437 (4)
O10.649 (3)0.431 (3)0.481 (3)0.077 (8)0.5000
O21.472 (6)0.825 (6)0.988 (6)0.085 (17)0.2500
N11.1393 (7)1.1656 (6)0.6377 (5)0.0381 (11)
N20.8580 (8)1.0781 (6)0.6102 (6)0.0417 (12)
N30.8649 (8)0.5827 (6)0.8576 (6)0.0410 (12)
N41.1459 (8)0.6641 (6)0.8894 (6)0.0412 (12)
C11.0025 (9)1.0606 (7)0.6752 (6)0.0373 (13)
C21.0773 (11)1.2484 (7)0.5488 (7)0.0460 (16)
C30.9027 (10)1.1950 (7)0.5311 (7)0.0438 (15)
C41.3237 (13)1.1892 (12)0.6904 (10)0.079 (3)
C51.0038 (8)0.6731 (6)0.9367 (6)0.0345 (13)
C60.9239 (11)0.5192 (7)0.7591 (7)0.0489 (18)
C71.1016 (11)0.5709 (7)0.7800 (7)0.0488 (17)
C80.6757 (12)0.5606 (11)0.8712 (11)0.075 (3)
H10.75031.02300.61720.0501*
H21.14671.32990.50690.0552*
H30.82491.23080.47500.0525*
H4A1.35351.10360.66950.0946*
H4B1.34091.20750.78860.0946*
H4C1.39941.27200.64810.0946*
H51.25410.71200.92440.0495*
H60.85350.45170.68970.0587*
H71.17940.54680.72830.0585*
H8A0.65360.65200.86040.0899*
H8B0.65050.52520.96070.0899*
H8C0.60010.49020.80130.0899*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.0618 (3)0.02442 (17)0.02127 (17)0.01898 (14)0.00965 (13)0.00366 (11)
Cl10.048 (4)0.052 (3)0.048 (3)0.007 (3)0.007 (2)0.0020 (19)
Cl20.042 (2)0.053 (3)0.054 (3)0.0103 (18)0.001 (2)0.005 (3)
Cl30.0431 (18)0.098 (4)0.054 (3)0.011 (2)0.0086 (16)0.002 (3)
S10.1108 (15)0.0316 (8)0.0226 (8)0.0378 (9)0.0184 (8)0.0057 (6)
S20.0883 (12)0.0261 (7)0.0256 (7)0.0285 (8)0.0140 (8)0.0046 (6)
O10.045 (13)0.083 (17)0.119 (18)0.039 (12)0.024 (11)0.005 (12)
O20.10 (4)0.09 (3)0.08 (3)0.07 (3)0.00 (3)0.03 (2)
N10.055 (3)0.034 (3)0.027 (3)0.016 (3)0.009 (3)0.002 (2)
N20.058 (4)0.035 (3)0.034 (3)0.017 (3)0.006 (3)0.001 (3)
N30.064 (4)0.030 (3)0.034 (3)0.023 (3)0.005 (3)0.000 (2)
N40.062 (4)0.032 (3)0.034 (3)0.022 (3)0.007 (3)0.006 (3)
C10.063 (4)0.029 (3)0.022 (3)0.017 (3)0.009 (3)0.001 (3)
C20.085 (5)0.028 (3)0.030 (4)0.023 (4)0.019 (4)0.008 (3)
C30.065 (5)0.043 (4)0.029 (3)0.026 (4)0.005 (3)0.004 (3)
C40.088 (7)0.089 (8)0.061 (6)0.030 (6)0.016 (5)0.003 (5)
C50.054 (4)0.024 (3)0.029 (3)0.018 (3)0.007 (3)0.001 (3)
C60.093 (6)0.030 (3)0.028 (4)0.028 (4)0.004 (4)0.002 (3)
C70.088 (6)0.037 (4)0.035 (4)0.036 (4)0.016 (4)0.002 (3)
C80.066 (6)0.067 (6)0.091 (8)0.021 (5)0.008 (5)0.002 (5)
Geometric parameters (Å, º) top
Au1—S12.346 (3)N4—C71.359 (9)
Au1—S1i2.346 (3)C2—C31.335 (11)
Au1—S22.357 (3)C6—C71.358 (12)
Au1—S2i2.357 (3)N2—H10.880
S1—C11.728 (7)N4—H50.880
S2—C51.724 (7)C2—H20.950
N1—C11.343 (8)C3—H30.950
N1—C21.369 (10)C4—H4A0.980
N1—C41.473 (12)C4—H4B0.980
N2—C11.337 (10)C4—H4C0.980
N2—C31.372 (9)C6—H60.950
N3—C51.349 (7)C7—H70.950
N3—C61.376 (11)C8—H8A0.980
N3—C81.508 (12)C8—H8B0.980
N4—C51.330 (10)C8—H8C0.980
Au1···C1i3.296 (7)Cl2···H4Bv2.7643
Au1···C5i3.295 (8)Cl2···H52.0824
S1···N33.307 (7)Cl2···H8Avi2.8136
S1···N43.237 (8)Cl3···H12.0569
S1···C43.208 (10)Cl3···H3viii2.8093
S1···C52.914 (7)Cl3···H4Avii2.9945
S2···N1i3.307 (7)Cl3···H4Aix3.5285
S2···N2i3.345 (7)Cl3···H4Cix3.5966
S2···C1i2.962 (7)Cl3···H8A3.3446
S2···C83.262 (9)S1···H3ix3.5511
N2···C43.577 (13)S2···H6x3.5962
Cl1···Cl1ii3.092 (15)O1···H2ix2.3881
Cl1···Cl3ii2.774 (11)O1···H3xi2.8022
Cl1···O1ii3.12 (3)O1···H4Ciii2.8534
Cl1···C4iii3.599 (13)O1···H4Cix3.3203
Cl1···C7iv3.553 (13)O1···H62.4698
Cl2···Cl2v3.132 (14)O1···H7iv2.6153
Cl2···Cl3vi3.056 (10)O1···H8C3.3407
Cl2···O2v3.21 (6)O1···H8Cii3.5080
Cl2···N42.944 (9)O2···H4Av3.5179
Cl3···Cl1ii2.774 (11)O2···H4Bv2.6314
Cl3···Cl2vii3.056 (10)O2···H51.7920
Cl3···O1ii3.12 (3)O2···H8Avi2.9672
Cl3···O2vii3.37 (6)O2···H8Bx3.3241
Cl3···N22.927 (7)N1···H1ix3.5137
Cl3···C3viii3.569 (9)N2···H4Aix3.2795
S1···C2ix3.564 (8)N3···H5x3.5801
S1···C3ix3.529 (8)N4···H8Bx3.1510
S2···C6x3.523 (9)C2···H6xii3.5106
S2···C7x3.575 (8)C2···H7xii3.2504
O1···Cl1ii3.12 (3)C3···H4Aix3.4595
O1···Cl3ii3.12 (3)C3···H6xii3.1414
O1···O1ii3.21 (4)C4···H1ix3.5828
O1···C2ix3.25 (3)C4···H8Cxiii3.1802
O1···C3xi3.59 (3)C6···H2ix3.1308
O1···C63.27 (3)C7···H3ix3.2054
O1···C7iv3.49 (3)C7···H8Bx3.4185
O2···Cl2v3.21 (6)C8···H4Ciii3.5606
O2···Cl3vi3.37 (6)C8···H5x3.5325
O2···O2v3.34 (8)C8···H8Bxiv3.1932
O2···N42.67 (5)H1···Cl32.0569
O2···C4v3.46 (5)H1···N1ix3.5137
O2···C53.58 (5)H1···C4ix3.5828
N1···N2ix3.450 (9)H1···H4Aix3.0253
N2···Cl32.927 (7)H2···Cl1ix2.7646
N2···N1ix3.450 (9)H2···O1ix2.3881
N3···N4x3.500 (9)H2···C6ix3.1308
N4···Cl22.944 (9)H2···H6ix2.9169
N4···O22.67 (5)H2···H7xii2.9960
N4···N3x3.500 (9)H3···Cl1xii2.8538
C1···C3ix3.580 (11)H3···Cl3viii2.8093
C2···S1ix3.564 (8)H3···S1ix3.5511
C2···O1ix3.25 (3)H3···O1xii2.8022
C3···Cl3viii3.569 (9)H3···C7ix3.2054
C3···S1ix3.529 (8)H3···H4Aix3.3758
C3···O1xii3.59 (3)H3···H6xii2.9841
C3···C1ix3.580 (11)H3···H7ix2.9972
C4···Cl1xiii3.599 (13)H4A···Cl3vi2.9945
C4···O2v3.46 (5)H4A···Cl3ix3.5285
C5···O23.58 (5)H4A···O2v3.5179
C6···S2x3.523 (9)H4A···N2ix3.2795
C6···O13.27 (3)H4A···C3ix3.4595
C7···Cl1iv3.553 (13)H4A···H1ix3.0253
C7···S2x3.575 (8)H4A···H3ix3.3758
C7···O1iv3.49 (3)H4B···Cl2v2.7643
S1···H12.9538H4B···O2v2.6314
S1···H4A3.0961H4B···H8Bxiii3.5878
S1···H4B3.1693H4B···H8Cxiii2.8858
S1···H53.5117H4C···Cl1xiii2.6899
S1···H8A3.4393H4C···Cl1ix3.4012
S2···H4Bi3.2804H4C···Cl3ix3.5966
S2···H52.9289H4C···O1xiii2.8534
S2···H8A3.2192H4C···O1ix3.3203
S2···H8B3.1757H4C···C8xiii3.5606
N1···H12.9998H4C···H6xiii3.5138
N1···H33.1152H4C···H8Cxiii2.5911
N2···H23.0876H5···Cl22.0824
N3···H52.9949H5···O21.7920
N3···H73.1224H5···N3x3.5801
N4···H63.0973H5···C8x3.5325
C1···H23.1160H5···H8Bx2.8963
C1···H33.1339H6···Cl12.8205
C1···H4A2.7595H6···S2x3.5962
C1···H4B2.7586H6···O12.4698
C1···H4C3.2678H6···C2xi3.5106
C2···H13.0124H6···C3xi3.1414
C2···H4A3.1673H6···H2ix2.9169
C2···H4B3.1366H6···H3xi2.9841
C2···H4C2.6271H6···H4Ciii3.5138
C4···H22.8382H7···Cl1iv2.6812
C5···H63.1341H7···O1iv2.6153
C5···H73.1287H7···C2xi3.2504
C5···H8A2.8045H7···H2xi2.9960
C5···H8B2.8101H7···H3ix2.9972
C5···H8C3.3066H7···H8Bx3.4157
C6···H53.0223H8A···Cl1ii3.5245
C6···H8A3.1646H8A···Cl2vii2.8136
C6···H8B3.1894H8A···Cl33.3446
C6···H8C2.6454H8A···O2vii2.9672
C8···H62.8581H8A···H8Bxiv3.2584
H1···H32.4479H8B···O2x3.3241
H2···H32.4603H8B···N4x3.1510
H2···H4A3.5065H8B···C7x3.4185
H2···H4B3.4730H8B···C8xiv3.1932
H2···H4C2.5753H8B···H4Biii3.5878
H5···H72.4270H8B···H5x2.8963
H6···H72.4911H8B···H7x3.4157
H6···H8A3.4952H8B···H8Axiv3.2584
H6···H8B3.5235H8B···H8Bxiv2.5580
H6···H8C2.5911H8B···H8Cxiv3.2844
Cl1···H2ix2.7646H8C···Cl13.5181
Cl1···H3xi2.8538H8C···Cl1ii3.2753
Cl1···H4Ciii2.6899H8C···O13.3407
Cl1···H4Cix3.4012H8C···O1ii3.5080
Cl1···H62.8205H8C···C4iii3.1802
Cl1···H7iv2.6812H8C···H4Biii2.8858
Cl1···H8Aii3.5245H8C···H4Ciii2.5911
Cl1···H8C3.5181H8C···H8Bxiv3.2844
Cl1···H8Cii3.2753
S1—Au1—S1i180.00 (10)N4—C7—C6106.4 (8)
S1—Au1—S289.47 (9)C1—N2—H1125.035
S1—Au1—S2i90.53 (9)C3—N2—H1125.031
S1i—Au1—S290.53 (9)C5—N4—H5124.534
S1i—Au1—S2i89.47 (9)C7—N4—H5124.532
S2—Au1—S2i180.00 (9)N1—C2—H2125.792
Au1—S1—C1107.0 (3)C3—C2—H2125.788
Au1—S2—C5106.6 (3)N2—C3—H3126.876
C1—N1—C2108.6 (6)C2—C3—H3126.870
C1—N1—C4124.5 (7)N1—C4—H4A109.470
C2—N1—C4126.8 (6)N1—C4—H4B109.469
C1—N2—C3109.9 (6)N1—C4—H4C109.471
C5—N3—C6109.0 (6)H4A—C4—H4B109.473
C5—N3—C8125.3 (7)H4A—C4—H4C109.471
C6—N3—C8125.7 (6)H4B—C4—H4C109.472
C5—N4—C7110.9 (6)N3—C6—H6126.437
S1—C1—N1126.3 (6)C7—C6—H6126.432
S1—C1—N2126.8 (5)N4—C7—H7126.797
N1—C1—N2106.8 (6)C6—C7—H7126.796
N1—C2—C3108.4 (6)N3—C8—H8A109.472
N2—C3—C2106.3 (7)N3—C8—H8B109.471
S2—C5—N3127.0 (6)N3—C8—H8C109.470
S2—C5—N4126.4 (5)H8A—C8—H8B109.474
N3—C5—N4106.5 (6)H8A—C8—H8C109.474
N3—C6—C7107.1 (6)H8B—C8—H8C109.467
S1—Au1—S2—C51.26 (10)C4—N1—C1—N2177.4 (7)
S2—Au1—S1—C1176.45 (11)C4—N1—C2—C3177.2 (7)
S1—Au1—S2i—C5i178.74 (10)C1—N2—C3—C20.1 (8)
S2i—Au1—S1—C13.55 (11)C3—N2—C1—S1176.7 (5)
S1i—Au1—S2—C5178.74 (10)C3—N2—C1—N10.1 (7)
S2—Au1—S1i—C1i3.55 (11)C5—N3—C6—C70.6 (7)
S1i—Au1—S2i—C5i1.26 (10)C6—N3—C5—S2178.0 (5)
S2i—Au1—S1i—C1i176.45 (11)C6—N3—C5—N40.9 (7)
Au1—S1—C1—N193.7 (5)C8—N3—C5—S24.6 (10)
Au1—S1—C1—N290.4 (5)C8—N3—C5—N4178.2 (7)
Au1—S2—C5—N392.5 (5)C8—N3—C6—C7178.0 (7)
Au1—S2—C5—N490.9 (5)C5—N4—C7—C60.4 (8)
C1—N1—C2—C30.0 (7)C7—N4—C5—S2177.9 (5)
C2—N1—C1—S1176.7 (5)C7—N4—C5—N30.8 (7)
C2—N1—C1—N20.1 (7)N1—C2—C3—N20.0 (8)
C4—N1—C1—S16.0 (10)N3—C6—C7—N40.1 (8)
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+1, z+1; (iii) x1, y1, z; (iv) x+2, y+1, z+1; (v) x+3, y+2, z+2; (vi) x+1, y, z; (vii) x1, y, z; (viii) x+1, y+2, z+1; (ix) x+2, y+2, z+1; (x) x+2, y+1, z+2; (xi) x, y1, z; (xii) x, y+1, z; (xiii) x+1, y+1, z; (xiv) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···Cl30.882.062.927 (7)170
N4—H5···Cl20.882.082.944 (9)166
N4—H5···O20.881.792.67 (5)174
 

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