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The structures of five gold complexes involving piperidine or pyrrolidine, either as neutral ligands or protonated counter-cations, are presented.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902300854X/yz2040sup1.cif
Contains datablocks 2, 3, 4, 6, 7, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902300854X/yz20402sup2.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902300854X/yz20403sup3.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902300854X/yz20404sup4.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902300854X/yz20406sup5.hkl
Contains datablock 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902300854X/yz20407sup6.hkl
Contains datablock 7

CCDC references: 2113940; 2113939; 2113938; 2113937; 2297985

Computing details top

Data collection: CrysAlis PRO, Version 1.171.36.28 (Agilent, 2014) for (2); CrysAlis PRO, Version 1.171.37.35 (Agilent, 2014) for (3), (4), (6), (7). Cell refinement: CrysAlis PRO, Version 1.171.36.28 (Agilent, 2014) for (2); CrysAlis PRO, Version 1.171.37.35 (Agilent, 2014) for (3), (4), (6), (7). Data reduction: CrysAlis PRO, Version 1.171.36.28 (Agilent, 2014) for (2); CrysAlis PRO, Version 1.171.37.35 (Agilent, 2014) for (3), (4), (6), (7). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Siemens XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015).

Bromido(pyrrolidine-κN)gold(I) bis(pyrrolidine-κN)gold(I) bromide (2) top
Crystal data top
[AuBr(C4H9N)]·[Au(C4H9N)2]BrDx = 2.840 Mg m3
Mr = 767.12Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 7080 reflections
a = 14.8040 (11) Åθ = 2.5–29.3°
b = 12.4631 (6) ŵ = 20.78 mm1
c = 19.4486 (8) ÅT = 100 K
V = 3588.3 (3) Å3Plate, colourless
Z = 80.08 × 0.08 × 0.01 mm
F(000) = 2784
Data collection top
Oxford Diffraction Xcalibur, Eos
diffractometer
4461 independent reflections
Radiation source: fine-focus sealed tube3055 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm-1Rint = 0.143
ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(CrysAlisPro; Agilent, 2014)
h = 1919
Tmin = 0.287, Tmax = 0.819k = 1616
129826 measured reflectionsl = 2525
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)] = 0.051Hydrogen site location: mixed
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0601P)2 + 57.3562P]
where P = (Fo2 + 2Fc2)/3
4461 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 7.82 e Å3
90 restraintsΔρmin = 2.45 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Au10.22755 (3)0.62223 (3)0.35070 (2)0.01738 (12)
Au20.24402 (3)0.37177 (3)0.36733 (2)0.02106 (13)
Br10.24081 (9)0.62289 (10)0.47285 (6)0.0319 (3)
Br20.47574 (7)0.62096 (9)0.29066 (7)0.0265 (3)
N110.2072 (6)0.6225 (7)0.2457 (5)0.0198 (18)
H010.154 (5)0.613 (8)0.238 (5)0.00 (3)*
C120.2422 (9)0.7142 (9)0.2053 (6)0.024 (3)
H12A0.3060330.7288190.2172890.029*
H12B0.2061370.7795400.2143220.029*
C130.2342 (13)0.6814 (11)0.1315 (7)0.051 (4)
H13A0.2857010.7095930.1045280.061*
H13B0.1773880.7091070.1114260.061*
C140.2346 (11)0.5599 (10)0.1315 (7)0.042 (4)
H14A0.1782280.5316390.1109690.051*
H14B0.2867000.5321250.1050080.051*
C150.2417 (10)0.5284 (9)0.2057 (7)0.030 (4)
H15A0.2047790.4638190.2150900.036*
H15B0.3052810.5128310.2180520.036*
N210.3785 (7)0.3993 (7)0.3701 (5)0.026 (2)
H020.396 (7)0.459 (7)0.359 (6)0.01 (3)*
C220.4148 (9)0.3975 (12)0.4418 (6)0.040 (3)
H22A0.3976470.3304680.4657780.047*
H22B0.3923870.4595980.4686090.047*
C230.5151 (9)0.4038 (11)0.4319 (8)0.046 (4)
H23A0.5474900.3730810.4718740.055*
H23B0.5348420.4790340.4253490.055*
C240.5321 (8)0.3377 (11)0.3674 (8)0.046 (4)
H24A0.5757590.3743220.3367880.056*
H24B0.5563290.2660400.3794090.056*
C250.4417 (8)0.3276 (11)0.3330 (7)0.038 (3)
H25A0.4461560.3489980.2840580.046*
H25B0.4202350.2524150.3351480.046*
N310.1091 (8)0.3412 (8)0.3728 (6)0.033 (2)
H030.105 (11)0.278 (7)0.362 (8)0.05 (5)*
C320.0779 (10)0.3300 (13)0.4453 (7)0.050 (3)
H32A0.0947690.2590620.4642010.060*0.64 (2)
H32B0.1043740.3867780.4746780.060*0.64 (2)
H32C0.0287840.2762810.4481430.060*0.36 (2)
H32D0.1283720.3058670.4748690.060*0.36 (2)
C330.0217 (12)0.341 (2)0.4413 (11)0.051 (6)0.64 (2)
H33A0.0448270.3799240.4821760.061*0.64 (2)
H33B0.0507300.2699180.4392480.061*0.64 (2)
C340.0420 (11)0.404 (2)0.3768 (13)0.058 (8)0.64 (2)
H34A0.0831970.3633280.3464410.070*0.64 (2)
H34B0.0706570.4737160.3883090.070*0.64 (2)
C350.0453 (8)0.4212 (10)0.3433 (7)0.032 (3)
H35A0.0672220.4949430.3520720.039*0.64 (2)
H35B0.0396760.4108290.2930190.039*0.64 (2)
H35C0.0066570.3847120.3213480.039*0.36 (2)
H35D0.0759750.4662000.3084900.039*0.36 (2)
C33'0.045 (4)0.435 (3)0.4683 (12)0.072 (17)*0.36 (2)
H33C0.0941190.4760470.4906510.087*0.36 (2)
H33D0.0054920.4264700.5011450.087*0.36 (2)
C34'0.014 (2)0.488 (2)0.4031 (12)0.035 (10)*0.36 (2)
H34C0.0523310.4947910.4027250.042*0.36 (2)
H34D0.0405000.5613370.3998370.042*0.36 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.0260 (2)0.01228 (19)0.0139 (2)0.00333 (18)0.00074 (14)0.00077 (16)
Au20.0371 (3)0.0123 (2)0.0138 (2)0.00283 (16)0.00284 (15)0.0012 (2)
Br10.0612 (8)0.0222 (6)0.0122 (6)0.0090 (6)0.0032 (5)0.0016 (5)
Br20.0183 (5)0.0201 (5)0.0410 (7)0.0001 (5)0.0013 (4)0.0055 (5)
N110.018 (4)0.017 (4)0.024 (5)0.003 (4)0.003 (4)0.003 (4)
C120.030 (8)0.024 (6)0.017 (8)0.007 (5)0.005 (5)0.001 (5)
C130.076 (12)0.058 (10)0.020 (9)0.018 (9)0.007 (8)0.000 (8)
C140.062 (10)0.047 (9)0.018 (8)0.020 (7)0.004 (7)0.015 (7)
C150.042 (9)0.027 (6)0.021 (9)0.013 (5)0.004 (5)0.004 (6)
N210.045 (6)0.009 (4)0.023 (6)0.001 (4)0.011 (5)0.000 (4)
C220.051 (9)0.048 (8)0.019 (7)0.013 (7)0.020 (6)0.009 (6)
C230.037 (8)0.039 (8)0.063 (11)0.006 (6)0.026 (7)0.004 (7)
C240.029 (7)0.032 (7)0.078 (13)0.004 (6)0.008 (8)0.014 (8)
C250.031 (7)0.038 (7)0.045 (9)0.006 (6)0.008 (6)0.014 (6)
N310.047 (6)0.024 (5)0.027 (5)0.007 (5)0.006 (5)0.001 (5)
C320.048 (5)0.061 (5)0.042 (5)0.009 (4)0.005 (4)0.008 (4)
C330.041 (8)0.064 (16)0.048 (13)0.003 (10)0.012 (8)0.021 (11)
C340.033 (8)0.073 (18)0.069 (16)0.001 (10)0.010 (9)0.040 (14)
C350.037 (7)0.028 (6)0.033 (7)0.001 (5)0.004 (5)0.003 (5)
Geometric parameters (Å, º) top
Au1—N112.065 (9)C24—H24A0.9900
Au1—Br12.3837 (12)C24—H24B0.9900
Au1—Au23.1476 (6)C25—H25A0.9900
Au1—Au2i3.1551 (6)C25—H25B0.9900
Au2—N212.021 (11)N31—C351.488 (13)
Au2—N312.036 (12)N31—C321.490 (14)
N11—C121.480 (12)N31—H030.81 (7)
N11—C151.497 (12)C32—C33'1.460 (19)
N11—H010.81 (7)C32—C331.483 (17)
C12—C131.496 (16)C32—H32A0.9900
C12—H12A0.9900C32—H32B0.9900
C12—H12B0.9900C32—H32C0.9900
C13—C141.514 (17)C32—H32D0.9900
C13—H13A0.9900C33—C341.508 (19)
C13—H13B0.9900C33—H33A0.9900
C14—C151.500 (16)C33—H33B0.9900
C14—H14A0.9900C34—C351.463 (17)
C14—H14B0.9900C34—H34A0.9900
C15—H15A0.9900C34—H34B0.9900
C15—H15B0.9900C35—C34'1.504 (18)
N21—C251.481 (13)C35—H35A0.9900
N21—C221.496 (12)C35—H35B0.9900
N21—H020.81 (7)C35—H35C0.9900
C22—C231.500 (15)C35—H35D0.9900
C22—H22A0.9900C33'—C34'1.51 (2)
C22—H22B0.9900C33'—H33C0.9900
C23—C241.523 (17)C33'—H33D0.9900
C23—H23A0.9900C34'—H34C0.9900
C23—H23B0.9900C34'—H34D0.9900
C24—C251.501 (15)
N11—Au1—Br1176.3 (3)C25—C24—H24B110.7
N11—Au1—Au296.6 (2)C23—C24—H24B110.7
Br1—Au1—Au283.95 (3)H24A—C24—H24B108.8
N11—Au1—Au2i96.8 (2)N21—C25—C24107.2 (9)
Br1—Au1—Au2i83.31 (3)N21—C25—H25A110.3
Au2—Au1—Au2i163.074 (19)C24—C25—H25A110.3
N21—Au2—N31175.4 (4)N21—C25—H25B110.3
N21—Au2—Au184.9 (2)C24—C25—H25B110.3
N31—Au2—Au196.6 (3)H25A—C25—H25B108.5
N21—Au2—Au1ii92.2 (2)C35—N31—C32103.3 (9)
N31—Au2—Au1ii87.2 (3)C35—N31—Au2118.5 (8)
Au1—Au2—Au1ii167.78 (2)C32—N31—Au2111.8 (9)
C12—N11—C15102.1 (8)C35—N31—H03119 (10)
C12—N11—Au1118.3 (7)C32—N31—H0398 (10)
C15—N11—Au1117.5 (7)Au2—N31—H03104 (10)
C12—N11—H01111 (7)C33'—C32—N31108.0 (14)
C15—N11—H0197 (7)C33—C32—N31104.4 (11)
Au1—N11—H01109 (8)C33—C32—H32A110.9
N11—C12—C13105.7 (9)N31—C32—H32A110.9
N11—C12—H12A110.6C33—C32—H32B110.9
C13—C12—H12A110.6N31—C32—H32B110.9
N11—C12—H12B110.6H32A—C32—H32B108.9
C13—C12—H12B110.6C33'—C32—H32C110.1
H12A—C12—H12B108.7N31—C32—H32C110.1
C12—C13—C14105.9 (11)C33'—C32—H32D110.1
C12—C13—H13A110.6N31—C32—H32D110.1
C14—C13—H13A110.6H32C—C32—H32D108.4
C12—C13—H13B110.6C32—C33—C34107.0 (13)
C14—C13—H13B110.6C32—C33—H33A110.3
H13A—C13—H13B108.7C34—C33—H33A110.3
C15—C14—C13105.2 (10)C32—C33—H33B110.3
C15—C14—H14A110.7C34—C33—H33B110.3
C13—C14—H14A110.7H33A—C33—H33B108.6
C15—C14—H14B110.7C35—C34—C33105.6 (12)
C13—C14—H14B110.7C35—C34—H34A110.6
H14A—C14—H14B108.8C33—C34—H34A110.6
N11—C15—C14105.7 (9)C35—C34—H34B110.6
N11—C15—H15A110.6C33—C34—H34B110.6
C14—C15—H15A110.6H34A—C34—H34B108.7
N11—C15—H15B110.6C34—C35—N31107.0 (11)
C14—C15—H15B110.6N31—C35—C34'105.6 (12)
H15A—C15—H15B108.7C34—C35—H35A110.3
C25—N21—C22102.6 (9)N31—C35—H35A110.3
C25—N21—Au2120.5 (7)C34—C35—H35B110.3
C22—N21—Au2112.1 (8)N31—C35—H35B110.3
C25—N21—H02103 (8)H35A—C35—H35B108.6
C22—N21—H0298 (8)N31—C35—H35C110.6
Au2—N21—H02117 (8)C34'—C35—H35C110.6
N21—C22—C23103.6 (10)N31—C35—H35D110.6
N21—C22—H22A111.0C34'—C35—H35D110.6
C23—C22—H22A111.0H35C—C35—H35D108.8
N21—C22—H22B111.0C32—C33'—C34'103.8 (15)
C23—C22—H22B111.0C32—C33'—H33C111.0
H22A—C22—H22B109.0C34'—C33'—H33C111.0
C22—C23—C24103.9 (10)C32—C33'—H33D111.0
C22—C23—H23A111.0C34'—C33'—H33D111.0
C24—C23—H23A111.0H33C—C33'—H33D109.0
C22—C23—H23B111.0C35—C34'—C33'108.1 (14)
C24—C23—H23B111.0C35—C34'—H34C110.1
H23A—C23—H23B109.0C33'—C34'—H34C110.1
C25—C24—C23105.4 (10)C35—C34'—H34D110.1
C25—C24—H24A110.7C33'—C34'—H34D110.1
C23—C24—H24A110.7H34C—C34'—H34D108.4
N11—Au1—Au2—N21100.5 (4)Au2—N21—C22—C23172.4 (8)
Br1—Au1—Au2—N2183.2 (3)N21—C22—C23—C2436.5 (14)
Au2i—Au1—Au2—N2141.9 (3)C22—C23—C24—C2517.2 (16)
N11—Au1—Au2—N3183.9 (4)C22—N21—C25—C2431.0 (14)
Br1—Au1—Au2—N3192.4 (3)Au2—N21—C25—C24156.3 (9)
Au2i—Au1—Au2—N31133.7 (3)C23—C24—C25—N218.6 (16)
N11—Au1—Au2—Au1ii23.8 (3)Au1—Au2—N31—C3522.3 (9)
Br1—Au1—Au2—Au1ii159.83 (9)Au1ii—Au2—N31—C35146.0 (9)
Au2i—Au1—Au2—Au1ii118.48 (12)Au1—Au2—N31—C3297.7 (8)
Au2—Au1—N11—C12147.6 (8)Au1ii—Au2—N31—C3294.0 (8)
Au2i—Au1—N11—C1222.1 (8)C35—N31—C32—C33'35 (2)
Au2—Au1—N11—C1524.3 (8)Au2—N31—C32—C33'94 (2)
Au2i—Au1—N11—C15145.4 (8)C35—N31—C32—C3334.9 (16)
C15—N11—C12—C1338.1 (13)Au2—N31—C32—C33163.4 (13)
Au1—N11—C12—C13168.8 (9)N31—C32—C33—C3424 (2)
N11—C12—C13—C1424.3 (17)C32—C33—C34—C354 (3)
C12—C13—C14—C150.7 (19)C33—C34—C35—N3119 (3)
C12—N11—C15—C1437.7 (13)C32—N31—C35—C3433.4 (18)
Au1—N11—C15—C14169.0 (9)Au2—N31—C35—C34157.7 (15)
C13—C14—C15—N1122.9 (17)C32—N31—C35—C34'27.0 (19)
Au1—Au2—N21—C25138.4 (9)Au2—N31—C35—C34'97.3 (18)
Au1ii—Au2—N21—C2529.7 (9)N31—C32—C33'—C34'28 (4)
Au1—Au2—N21—C22100.7 (7)N31—C35—C34'—C33'11 (4)
Au1ii—Au2—N21—C2291.2 (7)C32—C33'—C34'—C3510 (4)
C25—N21—C22—C2341.7 (13)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H01···Br2iii0.81 (7)2.70 (7)3.498 (9)169 (9)
N21—H02···Br20.81 (7)2.69 (8)3.477 (10)162 (11)
C22—H22B···Br10.993.033.859 (13)142
N31—H03···Br2ii0.81 (7)2.68 (10)3.416 (12)151 (14)
C32—H32A···Br1ii0.992.973.763 (14)138
C33—H33A···Br1iv0.993.033.675 (18)124
Symmetry codes: (ii) x+1/2, y1/2, z; (iii) x1/2, y, z+1/2; (iv) x, y+1, z+1.
Trichlorido(piperidine-κN)gold(III) (3) top
Crystal data top
[AuCl3(C5H11N)]F(000) = 712
Mr = 388.46Dx = 2.729 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.47646 (16) ÅCell parameters from 13188 reflections
b = 6.57436 (11) Åθ = 2.4–30.7°
c = 16.9961 (3) ŵ = 16.34 mm1
β = 93.5133 (16)°T = 100 K
V = 945.36 (3) Å3Irregular, yellow
Z = 40.17 × 0.17 × 0.15 mm
Data collection top
Oxford Diffraction Xcalibur, Eos
diffractometer
2853 independent reflections
Radiation source: Enhance (Mo) X-ray Source2690 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm-1Rint = 0.037
ω scanθmax = 31.1°, θmin = 2.4°
Absorption correction: multi-scan
(CrysAlisPro; Agilent, 2014)
h = 1212
Tmin = 0.689, Tmax = 1.000k = 99
24604 measured reflectionsl = 2324
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.017H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.030 w = 1/[σ2(Fo2) + (0.0085P)2 + 0.3159P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.003
2853 reflectionsΔρmax = 0.92 e Å3
96 parametersΔρmin = 0.80 e Å3
0 restraintsExtinction correction: SHELXL2018/3 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00109 (7)
Special details top

Geometry. Non-bonded contacts:

3.7100 (0.0006) Au1 - Cl2_$2 3.3365 (0.0006) Au1 - Cl3_$5 3.8344 (0.0008) Cl1 - Cl2_$6 3.8204 (0.0009) Cl1 - Cl3_$5 3.8344 (0.0008) Cl2 - Cl1_$6 3.9775 (0.0012) Cl2 - Cl2_$2 3.8204 (0.0009) Cl3 - Cl1_$1 3.8012 (0.0006) Cl3 - Cl3_$1 3.8012 (0.0006) Cl3 - Cl3_$5

112.26 ( 0.02) Au1 - Cl1 - Cl2_$6 60.17 ( 0.02) Au1 - Cl1 - Cl3_$5 152.87 ( 0.03) Au1 - Cl2 - Cl1_$6 66.44 ( 0.02) Au1 - Cl2 - Cl2_$2 109.01 ( 0.02) Au1 - Cl3 - Cl1_$1 101.40 ( 0.03) Au1 - Cl3 - Cl3_$1 60.57 ( 0.02) Au1 - Cl3 - Cl3_$5 133.79 ( 0.02) Au1 - Cl3 - Au1_$1

Operators for generating equivalent atoms: $1 -x+1, y-1/2, -z+3/2 $2 -x+1, -y+1, -z+2 $5 -x+1, y+1/2, -z+3/2 $6 -x+1, -y+2, -z+2

Dihedral angle -8.35 ( 2.02) H01 - N11 - Au1 - Cl3

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.7482 (0.0032) x - 4.6421 (0.0018) y + 9.8430 (0.0029) z = 3.8214 (0.0031)

* 0.0275 (0.0005) Au1 * -0.0055 (0.0007) N11 * -0.0051 (0.0006) Cl1 * -0.0085 (0.0005) Cl2 * -0.0083 (0.0005) Cl3

Rms deviation of fitted atoms = 0.0138

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.50340 (2)0.60493 (2)0.86802 (2)0.00923 (4)
Cl10.28810 (7)0.81001 (9)0.87943 (4)0.01663 (12)
Cl20.62533 (7)0.74686 (9)0.97772 (3)0.01580 (12)
Cl30.38860 (7)0.46665 (9)0.75544 (3)0.01487 (12)
N110.6977 (2)0.4215 (3)0.85214 (12)0.0099 (4)
H010.659 (3)0.348 (4)0.8139 (18)0.023 (8)*
C120.7391 (3)0.2837 (4)0.92065 (15)0.0162 (5)
H12A0.6473010.1960290.9302910.019*
H12B0.7630170.3667290.9685010.019*
C130.8809 (3)0.1509 (4)0.90554 (16)0.0169 (5)
H13A0.8518420.0544010.8623440.020*
H13B0.9104810.0706640.9534890.020*
C141.0226 (3)0.2774 (4)0.88339 (15)0.0190 (6)
H14A1.0592990.3643320.9284300.023*
H14B1.1104770.1863970.8706360.023*
C150.9751 (3)0.4096 (4)0.81249 (16)0.0174 (5)
H15A0.9464030.3217520.7665220.021*
H15B1.0659060.4951270.7993040.021*
C160.8357 (3)0.5454 (4)0.82901 (15)0.0145 (5)
H16A0.8672520.6414100.8720080.017*
H16B0.8047040.6258740.7813170.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.00840 (5)0.00890 (5)0.01038 (5)0.00117 (3)0.00037 (3)0.00010 (3)
Cl10.0149 (3)0.0182 (3)0.0168 (3)0.0078 (2)0.0008 (2)0.0010 (2)
Cl20.0155 (3)0.0165 (3)0.0150 (3)0.0008 (2)0.0019 (2)0.0042 (2)
Cl30.0127 (3)0.0159 (3)0.0155 (3)0.0016 (2)0.0026 (2)0.0045 (2)
N110.0087 (10)0.0085 (10)0.0123 (10)0.0009 (8)0.0009 (8)0.0002 (7)
C120.0169 (13)0.0133 (12)0.0186 (13)0.0035 (10)0.0032 (10)0.0064 (10)
C130.0158 (13)0.0142 (12)0.0202 (13)0.0056 (10)0.0026 (10)0.0019 (10)
C140.0120 (13)0.0178 (13)0.0266 (14)0.0045 (10)0.0031 (11)0.0023 (11)
C150.0098 (12)0.0177 (13)0.0250 (14)0.0025 (10)0.0039 (10)0.0011 (10)
C160.0113 (12)0.0114 (11)0.0214 (13)0.0012 (10)0.0053 (10)0.0029 (10)
Geometric parameters (Å, º) top
Au1—N112.0718 (19)C12—H12A0.9900
Au1—Cl22.2757 (6)C12—H12B0.9900
Au1—Cl32.2817 (6)C13—H13A0.9900
Au1—Cl12.2868 (6)C13—H13B0.9900
N11—C161.498 (3)C14—H14A0.9900
N11—C121.500 (3)C14—H14B0.9900
C12—C131.520 (3)C15—H15A0.9900
C13—C141.527 (4)C15—H15B0.9900
C14—C151.520 (4)C16—H16A0.9900
C15—C161.520 (3)C16—H16B0.9900
N11—H010.86 (3)
N11—Au1—Cl291.19 (6)H12A—C12—H12B108.0
N11—Au1—Cl387.73 (6)C12—C13—H13A109.3
Cl2—Au1—Cl3177.91 (2)C14—C13—H13A109.3
N11—Au1—Cl1177.36 (6)C12—C13—H13B109.3
Cl2—Au1—Cl190.77 (2)C14—C13—H13B109.3
Cl3—Au1—Cl190.25 (2)H13A—C13—H13B107.9
C16—N11—C12112.49 (19)C15—C14—H14A109.8
C16—N11—Au1110.96 (14)C13—C14—H14A109.8
C12—N11—Au1113.61 (15)C15—C14—H14B109.8
N11—C12—C13111.5 (2)C13—C14—H14B109.8
C12—C13—C14111.8 (2)H14A—C14—H14B108.2
C15—C14—C13109.4 (2)C14—C15—H15A109.4
C14—C15—C16111.1 (2)C16—C15—H15A109.4
N11—C16—C15110.96 (19)C14—C15—H15B109.4
C16—N11—H01112 (2)C16—C15—H15B109.4
C12—N11—H01108 (2)H15A—C15—H15B108.0
Au1—N11—H0199 (2)N11—C16—H16A109.4
N11—C12—H12A109.3C15—C16—H16A109.4
C13—C12—H12A109.3N11—C16—H16B109.4
N11—C12—H12B109.3C15—C16—H16B109.4
C13—C12—H12B109.3H16A—C16—H16B108.0
C16—N11—C12—C1353.6 (3)C13—C14—C15—C1657.1 (3)
Au1—N11—C12—C13179.30 (16)C12—N11—C16—C1554.9 (3)
N11—C12—C13—C1454.2 (3)Au1—N11—C16—C15176.54 (17)
C12—C13—C14—C1555.8 (3)C14—C15—C16—N1157.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H01···Cl30.86 (3)2.57 (3)3.021 (2)114 (2)
N11—H01···Cl3i0.86 (3)2.79 (3)3.558 (2)150 (3)
C12—H12B···Cl1ii0.992.893.475 (3)119
C14—H14B···Cl1iii0.992.903.812 (3)154
C12—H12A···Cl2ii0.992.893.636 (3)133
C13—H13A···Cl3i0.992.833.661 (3)142
C15—H15B···Cl3iv0.992.883.713 (3)142
C16—H16B···Cl3v0.992.823.607 (2)137
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1, z+2; (iii) x+1, y1, z; (iv) x+1, y, z; (v) x+1, y+1/2, z+3/2.
Bis(piperidinium) tetrachloridoaurate(III) chloride (4) top
Crystal data top
(C5H12N)2[AuCl4]ClDx = 1.998 Mg m3
Mr = 546.53Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Iba2Cell parameters from 2523 reflections
a = 19.4014 (15) Åθ = 3.0–24.5°
b = 9.7612 (6) ŵ = 8.82 mm1
c = 19.1922 (11) ÅT = 100 K
V = 3634.6 (4) Å3Plate, yellow
Z = 80.10 × 0.05 × 0.03 mm
F(000) = 2096
Data collection top
Oxford Diffraction Xcalibur, Eos
diffractometer
4242 independent reflections
Radiation source: Enhance (Mo) X-ray Source2632 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm-1Rint = 0.075
ω scanθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan
(CrysAlisPro; Agilent, 2014)
h = 2425
Tmin = 0.718, Tmax = 1.000k = 1212
19554 measured reflectionsl = 2524
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0131P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4242 reflectionsΔρmax = 0.84 e Å3
105 parametersΔρmin = 0.86 e Å3
59 restraintsAbsolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.45 (3)
Special details top

Geometry. Non-bonded contacts:

3.9947 (0.0026) Au1 - Cl1_$1 3.8135 (0.0004) Au1 - Cl6_$4 3.0850 (0.0053) Cl3 - Cl3_$5

164.57 ( 0.12) Au1 - Cl1_$1 - Au1_$1 168.05 ( 0.18) Cl3 - Cl3_$5 - Au1_$5

Operators for generating equivalent atoms: $1 -x+1/2, y-1/2, z $4 x-1/2, -y+3/2, z $5 -x, -y+1, z

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.15024 (2)0.74808 (5)0.5000 (4)0.01752 (11)
Cl10.23809 (15)0.9043 (3)0.5022 (7)0.0293 (7)
Cl20.1479 (5)0.7502 (5)0.3813 (3)0.041 (4)
Cl30.06697 (15)0.5852 (3)0.5004 (8)0.0363 (8)
Cl40.1459 (5)0.7478 (6)0.6189 (2)0.041 (4)
Cl50.5000000.5000000.7497 (9)0.0209 (8)
Cl60.5000000.5000000.4997 (9)0.0212 (8)
N110.4450 (6)0.6793 (10)0.6243 (7)0.019 (3)*
H11A0.4702890.6555840.5862530.023*
H11B0.4631810.6356130.6619430.023*
C120.3724 (9)0.6341 (16)0.6143 (9)0.041 (5)*
H12A0.3712300.5337000.6069080.049*
H12B0.3530760.6786080.5722270.049*
C130.3277 (9)0.6715 (13)0.6786 (9)0.032 (5)*
H13A0.2794770.6419260.6708410.038*
H13B0.3454300.6236150.7204100.038*
C140.3301 (7)0.8260 (12)0.6901 (9)0.014 (4)*
H14A0.3072560.8731040.6507000.017*
H14B0.3048740.8494960.7333310.017*
C150.4040 (8)0.8740 (15)0.6958 (8)0.028 (4)*
H15A0.4240400.8376550.7395490.033*
H15B0.4044830.9752560.6989610.033*
C160.4494 (7)0.8302 (12)0.6350 (8)0.026 (4)*
H16A0.4344760.8780410.5921510.031*
H16B0.4978500.8562310.6445710.031*
N210.4104 (6)0.6232 (10)0.3780 (7)0.024 (3)*
H22A0.4284020.5830840.3392870.028*
H22B0.4228090.5714870.4154220.028*
C220.3351 (7)0.6233 (14)0.3724 (9)0.035 (4)*
H23A0.3146920.6573010.4163770.042*
H23B0.3184570.5285850.3646360.042*
C230.3127 (10)0.7123 (14)0.3134 (9)0.052 (6)*
H24A0.2616990.7157980.3123860.062*
H24B0.3284820.6712090.2690460.062*
C240.3408 (8)0.8578 (14)0.3190 (11)0.037 (5)*
H25A0.3272450.9107840.2772070.045*
H25B0.3207730.9034120.3603780.045*
C250.4187 (8)0.8560 (14)0.3252 (9)0.033 (4)*
H26A0.4359240.9498810.3340720.040*
H26B0.4392820.8230890.2810000.040*
C260.4402 (8)0.7603 (14)0.3857 (8)0.036 (4)*
H21A0.4910800.7530180.3869220.043*
H21B0.4248170.8005770.4303850.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01711 (19)0.02022 (19)0.01522 (17)0.0008 (2)0.0003 (10)0.0000 (6)
Cl10.0294 (18)0.0271 (14)0.0313 (16)0.0094 (12)0.006 (5)0.000 (4)
Cl20.054 (10)0.041 (6)0.027 (7)0.015 (4)0.005 (5)0.008 (3)
Cl30.0258 (19)0.0326 (16)0.0503 (18)0.0116 (13)0.003 (6)0.012 (5)
Cl40.046 (9)0.071 (8)0.006 (5)0.003 (4)0.004 (4)0.003 (4)
Cl50.024 (2)0.0228 (18)0.0163 (17)0.003 (7)0.0000.000
Cl60.031 (2)0.0233 (18)0.0098 (16)0.0116 (16)0.0000.000
Geometric parameters (Å, º) top
Au1—Cl32.267 (3)C13—H13A0.9900
Au1—Cl22.278 (13)C13—H13B0.9900
Au1—Cl42.284 (11)C14—H14A0.9900
Au1—Cl12.287 (3)C14—H14B0.9900
N11—C121.489 (15)C15—H15A0.9900
N11—C161.490 (13)C15—H15B0.9900
C12—C131.553 (16)C16—H16A0.9900
C13—C141.525 (14)C16—H16B0.9900
C14—C151.514 (15)N21—H22A0.9100
C15—C161.523 (14)N21—H22B0.9100
N21—C221.465 (14)C22—H23A0.9900
N21—C261.466 (13)C22—H23B0.9900
C22—C231.491 (15)C23—H24A0.9900
C23—C241.526 (15)C23—H24B0.9900
C24—C251.517 (15)C24—H25A0.9900
C25—C261.547 (14)C24—H25B0.9900
N11—H11A0.9100C25—H26A0.9900
N11—H11B0.9100C25—H26B0.9900
C12—H12A0.9900C26—H21A0.9900
C12—H12B0.9900C26—H21B0.9900
Cl3—Au1—Cl289.8 (4)C16—C15—H15A108.8
Cl3—Au1—Cl488.2 (4)C14—C15—H15B108.8
Cl2—Au1—Cl4176.70 (12)C16—C15—H15B108.8
Cl3—Au1—Cl1177.0 (3)H15A—C15—H15B107.7
Cl2—Au1—Cl191.6 (3)N11—C16—H16A109.6
Cl4—Au1—Cl190.6 (4)C15—C16—H16A109.6
C12—N11—C16111.5 (11)N11—C16—H16B109.6
N11—C12—C13110.8 (12)C15—C16—H16B109.6
C14—C13—C12109.3 (11)H16A—C16—H16B108.1
C15—C14—C13110.2 (12)C22—N21—H22A108.8
C14—C15—C16113.9 (11)C26—N21—H22A108.8
N11—C16—C15110.5 (10)C22—N21—H22B108.8
C22—N21—C26113.6 (10)C26—N21—H22B108.8
N21—C22—C23110.3 (12)H22A—N21—H22B107.7
C22—C23—C24112.7 (12)N21—C22—H23A109.6
C25—C24—C23110.6 (12)C23—C22—H23A109.6
C24—C25—C26109.5 (12)N21—C22—H23B109.6
N21—C26—C25111.7 (11)C23—C22—H23B109.6
C12—N11—H11A109.3H23A—C22—H23B108.1
C16—N11—H11A109.3C22—C23—H24A109.1
C12—N11—H11B109.3C24—C23—H24A109.1
C16—N11—H11B109.3C22—C23—H24B109.1
H11A—N11—H11B108.0C24—C23—H24B109.1
N11—C12—H12A109.5H24A—C23—H24B107.8
C13—C12—H12A109.5C25—C24—H25A109.5
N11—C12—H12B109.5C23—C24—H25A109.5
C13—C12—H12B109.5C25—C24—H25B109.5
H12A—C12—H12B108.1C23—C24—H25B109.5
C14—C13—H13A109.8H25A—C24—H25B108.1
C12—C13—H13A109.8C24—C25—H26A109.8
C14—C13—H13B109.8C26—C25—H26A109.8
C12—C13—H13B109.8C24—C25—H26B109.8
H13A—C13—H13B108.3C26—C25—H26B109.8
C15—C14—H14A109.6H26A—C25—H26B108.2
C13—C14—H14A109.6N21—C26—H21A109.3
C15—C14—H14B109.6C25—C26—H21A109.3
C13—C14—H14B109.6N21—C26—H21B109.3
H14A—C14—H14B108.1C25—C26—H21B109.3
C14—C15—H15A108.8H21A—C26—H21B107.9
C16—N11—C12—C1359.6 (17)C26—N21—C22—C2356.0 (16)
N11—C12—C13—C1458.7 (17)N21—C22—C23—C2455.1 (18)
C12—C13—C14—C1554.6 (17)C22—C23—C24—C2555 (2)
C13—C14—C15—C1653.4 (16)C23—C24—C25—C2653.1 (18)
C12—N11—C16—C1555.6 (16)C22—N21—C26—C2556.3 (16)
C14—C15—C16—N1153.2 (16)C24—C25—C26—N2154.1 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···Cl60.912.323.150 (16)151
N11—H11B···Cl50.912.263.161 (16)172
C12—H12A···Cl4i0.992.823.788 (17)166
C13—H13A···Cl40.992.963.78 (2)141
C16—H16A···Cl3ii0.992.683.601 (16)155
N21—H22B···Cl60.912.313.150 (15)153
N21—H22A···Cl5iii0.912.353.246 (17)166
C22—H23B···Cl2i0.992.813.661 (14)144
C23—H24A···Cl20.992.603.47 (2)148
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x, y+1, z1/2.
Bis(pyrrolidinium) tetrabromidoaurate(III) bromide (6) top
Crystal data top
(C4H10N)2[AuBr4]BrDx = 2.880 Mg m3
Mr = 740.78Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, IbamCell parameters from 6924 reflections
a = 19.1275 (7) Åθ = 2.4–30.3°
b = 9.4396 (13) ŵ = 20.28 mm1
c = 18.9259 (17) ÅT = 100 K
V = 3417.2 (6) Å3Plate, red
Z = 80.15 × 0.12 × 0.03 mm
F(000) = 2688
Data collection top
Oxford Diffraction Xcalibur, Eos
diffractometer
2689 independent reflections
Radiation source: Enhance (Mo) X-ray Source2205 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.085
Detector resolution: 16.1419 pixels mm-1θmax = 31.0°, θmin = 2.1°
ω scanh = 2727
Absorption correction: multi-scan
(CrysAlisPro; Agilent, 2014)
k = 1213
Tmin = 0.177, Tmax = 1.000l = 2726
35669 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)] = 0.034Hydrogen site location: mixed
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0204P)2 + 17.1013P]
where P = (Fo2 + 2Fc2)/3
2689 reflections(Δ/σ)max = 0.001
88 parametersΔρmax = 2.21 e Å3
1 restraintΔρmin = 1.24 e Å3
Special details top

Geometry. Au···Br and Br···Br contacts:

3.6997 (0.0008) Au1 - Br2_$5 3.4585 (0.0003) Au1 - Br4 3.6997 (0.0008) Br2 - Au1_$3 3.3201 (0.0013) Br3 - Br3_$6 3.4585 (0.0003) Br4 - Au1_$7

171.61 ( 0.03) Au1 - Br2 - Au1_$3 149.92 ( 0.04) Au1 - Br3 - Br3_$6

Operators for generating equivalent atoms: $3 -x+1/2, y-1/2, z $4 x, y-1, z $5 -x+1/2, y+1/2, z $6 -x, -y+2, -z $7 -x, -y+1, -z $8 x, y, -z

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.14803 (2)0.71040 (3)0.0000000.01444 (7)
Br10.14858 (2)0.71441 (5)0.12839 (3)0.02063 (12)
Br20.22029 (4)0.49747 (8)0.0000000.02791 (18)
Br30.07792 (3)0.92257 (7)0.0000000.02033 (15)
Br40.0000000.5000000.0000000.01607 (19)
Br50.0000000.5000000.2500000.0268 (2)
N110.0999 (2)0.3577 (5)0.1304 (3)0.0271 (10)
H010.069 (3)0.423 (6)0.161 (3)0.05 (2)*
H020.101 (3)0.392 (7)0.079 (2)0.05 (2)*
C120.0578 (3)0.2271 (5)0.1206 (3)0.0299 (13)
H12A0.0645380.1875770.0726660.036*
H12B0.0074660.2465550.1279320.036*
C130.0852 (3)0.1262 (5)0.1763 (3)0.0248 (11)
H13A0.0765950.0263270.1628910.030*
H13B0.0635190.1448500.2228960.030*
C140.1628 (3)0.1595 (5)0.1772 (3)0.0280 (13)
H14A0.1870670.1125650.1373890.034*
H14B0.1844470.1283750.2221310.034*
C150.1659 (3)0.3205 (6)0.1699 (4)0.0316 (14)
H15A0.1668240.3666710.2168000.038*
H15B0.2078000.3498320.1428850.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01035 (12)0.01443 (13)0.01854 (14)0.00078 (9)0.0000.000
Br10.0196 (2)0.0233 (3)0.0190 (3)0.00056 (19)0.00249 (19)0.0003 (2)
Br20.0256 (4)0.0281 (4)0.0300 (4)0.0144 (3)0.0000.000
Br30.0190 (3)0.0160 (3)0.0260 (4)0.0047 (2)0.0000.000
Br40.0138 (4)0.0170 (4)0.0174 (5)0.0002 (3)0.0000.000
Br50.0195 (5)0.0433 (6)0.0177 (5)0.0000.0000.000
N110.023 (2)0.030 (3)0.028 (3)0.005 (2)0.002 (2)0.007 (2)
C120.033 (3)0.021 (3)0.036 (3)0.002 (2)0.012 (3)0.003 (2)
C130.031 (3)0.017 (2)0.027 (3)0.001 (2)0.001 (2)0.005 (2)
C140.024 (3)0.021 (3)0.039 (3)0.006 (2)0.003 (2)0.013 (3)
C150.016 (2)0.032 (3)0.046 (4)0.001 (2)0.002 (3)0.012 (3)
Geometric parameters (Å, º) top
Au1—Br32.4102 (7)C12—H12B0.9900
Au1—Br12.4303 (5)C13—C141.517 (7)
Au1—Br1i2.4303 (5)C13—H13A0.9900
Au1—Br22.4393 (8)C13—H13B0.9900
N11—C121.484 (7)C14—C151.527 (7)
N11—C151.508 (7)C14—H14A0.9900
N11—H011.03 (4)C14—H14B0.9900
N11—H021.02 (4)C15—H15A0.9900
C12—C131.514 (7)C15—H15B0.9900
C12—H12A0.9900
Br3—Au1—Br189.399 (13)C12—C13—C14102.5 (4)
Br3—Au1—Br1i89.399 (13)C12—C13—H13A111.3
Br1—Au1—Br1i178.15 (3)C14—C13—H13A111.3
Br3—Au1—Br2179.29 (3)C12—C13—H13B111.3
Br1—Au1—Br290.592 (13)C14—C13—H13B111.3
Br1i—Au1—Br290.593 (13)H13A—C13—H13B109.2
C12—N11—C15108.8 (4)C13—C14—C15104.1 (4)
C12—N11—H01105 (4)C13—C14—H14A110.9
C15—N11—H01110 (4)C15—C14—H14A110.9
C12—N11—H0299 (4)C13—C14—H14B110.9
C15—N11—H02122 (4)C15—C14—H14B110.9
H01—N11—H02111 (5)H14A—C14—H14B109.0
N11—C12—C13104.4 (4)N11—C15—C14104.2 (4)
N11—C12—H12A110.9N11—C15—H15A110.9
C13—C12—H12A110.9C14—C15—H15A110.9
N11—C12—H12B110.9N11—C15—H15B110.9
C13—C12—H12B110.9C14—C15—H15B110.9
H12A—C12—H12B108.9H15A—C15—H15B108.9
C15—N11—C12—C1320.1 (6)C12—N11—C15—C144.5 (6)
N11—C12—C13—C1436.7 (6)C13—C14—C15—N1127.3 (6)
C12—C13—C14—C1539.7 (6)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H01···Br51.03 (4)2.26 (5)3.253 (5)161 (5)
N11—H02···Br21.02 (4)2.90 (6)3.624 (5)128 (5)
N11—H02···Br41.02 (4)2.65 (6)3.398 (5)130 (5)
C12—H12B···Br1ii0.993.013.989 (6)171
C15—H15A···Br1iii0.993.053.847 (7)139
C15—H15B···Br1iv0.993.043.770 (5)131
C15—H15B···Br20.993.053.769 (6)130
C12—H12A···Br3v0.992.873.691 (6)141
Symmetry codes: (ii) x, y+1, z; (iii) x, y+1, z+1/2; (iv) x+1/2, y1/2, z; (v) x, y1, z.
Tribromido(piperidine-κN)gold(III) dichloromethane monosolvate (7) top
Crystal data top
[AuBr3(C5H11N)]·CH2Cl2F(000) = 1096
Mr = 606.77Dx = 2.938 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.3473 (3) ÅCell parameters from 8200 reflections
b = 22.0860 (8) Åθ = 2.7–30.8°
c = 8.5066 (3) ŵ = 19.82 mm1
β = 96.423 (3)°T = 100 K
V = 1371.71 (9) Å3Block, red
Z = 40.15 × 0.12 × 0.10 mm
Data collection top
Oxford Diffraction Xcalibur, Eos
diffractometer
4139 independent reflections
Radiation source: Enhance (Mo) X-ray Source3658 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm-1Rint = 0.043
ω scanθmax = 30.9°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlisPro; Agilent, 2014)
h = 1010
Tmin = 0.574, Tmax = 1.000k = 3131
36043 measured reflectionsl = 1211
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.024H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.039 w = 1/[σ2(Fo2) + (0.0061P)2 + 2.1369P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
4139 reflectionsΔρmax = 0.84 e Å3
123 parametersΔρmin = 0.83 e Å3
0 restraintsExtinction correction: SHELXL2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00041 (2)
Special details top

Geometry. Non-bonded contacts:

3.5658 (0.0004) Au1 - Br2_$3 3.4678 (0.0004) Au1 - Br3_$1 3.5658 (0.0004) Br2 - Au1_$1 3.3817 (0.0004) Br2 - Br3_$5 3.4678 (0.0004) Br3 - Au1_$3 3.3817 (0.0004) Br3 - Br2_$6 3.5618 (0.0021) Cl1 - Cl1_$7

88.50 ( 0.01) Au1 - Br2 - Au1_$1 158.46 ( 0.01) Au1 - Br2 - Br3_$5 90.79 ( 0.01) Au1 - Br3 - Au1_$3 155.37 ( 0.01) Au1 - Br3 - Br2_$6 146.38 ( 0.13) C1 - Cl1 - Cl1_$7

Operators for generating equivalent atoms: $1 x, -y+1/2, z+1/2 $3 x, -y+1/2, z-1/2 $5 x+1, -y+1/2, z+1/2 $6 x-1, -y+1/2, z-1/2 $7 -x, -y+1, -z+1

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.51277 (2)0.24454 (2)0.25555 (2)0.00781 (4)
Br10.52418 (4)0.35307 (2)0.21990 (4)0.01219 (7)
Br20.79078 (4)0.24741 (2)0.43841 (4)0.01246 (7)
Br30.24299 (4)0.24137 (2)0.06300 (4)0.01363 (7)
N110.5152 (4)0.15094 (13)0.2928 (3)0.0105 (6)
H010.564 (5)0.1462 (17)0.388 (4)0.010 (9)*
C120.3327 (5)0.12067 (16)0.2919 (4)0.0166 (7)
H12A0.2626600.1253370.1862720.020*
H12B0.2626250.1404850.3704570.020*
C130.3548 (5)0.05401 (17)0.3310 (4)0.0206 (8)
H13A0.2326560.0346500.3245840.025*
H13B0.4145080.0493130.4405580.025*
C140.4697 (5)0.02288 (17)0.2170 (4)0.0219 (8)
H14A0.4882690.0201150.2475790.026*
H14B0.4046730.0242180.1086120.026*
C150.6531 (5)0.05400 (17)0.2194 (4)0.0212 (8)
H15A0.7243000.0346100.1410070.025*
H15B0.7225660.0491340.3253120.025*
C160.6307 (5)0.12090 (16)0.1816 (4)0.0158 (7)
H16A0.7525870.1404700.1899690.019*
H16B0.5725960.1258820.0716250.019*
C10.0245 (5)0.37793 (17)0.2600 (4)0.0185 (7)
H1A0.1451170.3574390.2730570.022*
H1B0.0718600.3464080.2526390.022*
Cl10.00338 (15)0.42462 (5)0.42603 (12)0.0294 (2)
Cl20.00380 (16)0.42122 (5)0.08506 (12)0.0327 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.00905 (6)0.00586 (6)0.00833 (6)0.00023 (5)0.00018 (4)0.00005 (5)
Br10.01637 (16)0.00648 (16)0.01348 (16)0.00051 (12)0.00062 (12)0.00047 (12)
Br20.01135 (14)0.01168 (17)0.01346 (15)0.00178 (12)0.00249 (11)0.00151 (12)
Br30.01223 (15)0.01432 (18)0.01331 (15)0.00090 (13)0.00310 (12)0.00090 (13)
N110.0165 (14)0.0063 (14)0.0080 (13)0.0013 (11)0.0018 (11)0.0003 (10)
C120.0186 (18)0.0109 (18)0.0216 (18)0.0050 (14)0.0082 (14)0.0023 (14)
C130.032 (2)0.0105 (19)0.0203 (18)0.0055 (15)0.0068 (16)0.0003 (15)
C140.038 (2)0.0085 (18)0.0198 (19)0.0001 (16)0.0037 (17)0.0009 (14)
C150.031 (2)0.0091 (19)0.0233 (19)0.0028 (15)0.0042 (16)0.0017 (15)
C160.0212 (18)0.0104 (18)0.0162 (17)0.0036 (14)0.0038 (14)0.0002 (14)
C10.0178 (18)0.0147 (18)0.0239 (19)0.0012 (14)0.0061 (15)0.0030 (15)
Cl10.0363 (6)0.0285 (6)0.0232 (5)0.0024 (4)0.0023 (4)0.0021 (4)
Cl20.0477 (7)0.0282 (6)0.0239 (5)0.0064 (5)0.0118 (5)0.0081 (4)
Geometric parameters (Å, º) top
Au1—N112.091 (3)C12—H12A0.9900
Au1—Br12.4187 (4)C12—H12B0.9900
Au1—Br22.4260 (3)C13—H13A0.9900
Au1—Br32.4270 (3)C13—H13B0.9900
N11—C161.495 (4)C14—H14A0.9900
N11—C121.497 (4)C14—H14B0.9900
C12—C131.514 (5)C15—H15A0.9900
C13—C141.520 (5)C15—H15B0.9900
C14—C151.511 (5)C16—H16A0.9900
C15—C161.517 (5)C16—H16B0.9900
C1—Cl21.761 (4)C1—H1A0.9900
C1—Cl11.769 (4)C1—H1B0.9900
N11—H010.85 (4)
N11—Au1—Br1177.24 (8)C14—C13—H13A109.5
N11—Au1—Br286.35 (8)C12—C13—H13B109.5
Br1—Au1—Br290.913 (12)C14—C13—H13B109.5
N11—Au1—Br393.80 (8)H13A—C13—H13B108.1
Br1—Au1—Br388.920 (12)C15—C14—H14A109.6
Br2—Au1—Br3177.454 (13)C13—C14—H14A109.6
C16—N11—C12111.7 (3)C15—C14—H14B109.6
C16—N11—Au1109.8 (2)C13—C14—H14B109.6
C12—N11—Au1116.6 (2)H14A—C14—H14B108.2
N11—C12—C13111.1 (3)C14—C15—H15A109.4
C12—C13—C14110.7 (3)C16—C15—H15A109.4
C15—C14—C13110.1 (3)C14—C15—H15B109.4
C14—C15—C16111.4 (3)C16—C15—H15B109.4
N11—C16—C15110.7 (3)H15A—C15—H15B108.0
Cl2—C1—Cl1110.5 (2)N11—C16—H16A109.5
C16—N11—H01110 (2)C15—C16—H16A109.5
C12—N11—H01104 (2)N11—C16—H16B109.5
Au1—N11—H01105 (3)C15—C16—H16B109.5
N11—C12—H12A109.4H16A—C16—H16B108.1
C13—C12—H12A109.4Cl2—C1—H1A109.5
N11—C12—H12B109.4Cl1—C1—H1A109.5
C13—C12—H12B109.4Cl2—C1—H1B109.5
H12A—C12—H12B108.0Cl1—C1—H1B109.5
C12—C13—H13A109.5H1A—C1—H1B108.1
C16—N11—C12—C1356.4 (4)C13—C14—C15—C1656.3 (4)
Au1—N11—C12—C13176.2 (2)C12—N11—C16—C1555.8 (4)
N11—C12—C13—C1456.4 (4)Au1—N11—C16—C15173.2 (2)
C12—C13—C14—C1556.3 (4)C14—C15—C16—N1156.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H01···Br1i0.85 (4)2.87 (4)3.627 (3)148 (3)
C14—H14A···Br1ii0.992.823.788 (4)167
C16—H16B···Br1iii0.993.013.960 (3)161
C1—H1B···Br1iv0.992.953.695 (4)133
C1—H1B···Br2iv0.992.943.761 (4)141
C12—H12A···Cl1iii0.992.973.855 (4)150
C15—H15B···Cl2v0.992.933.849 (4)156
C1—H1A···Br10.992.873.765 (4)150
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x1, y, z; (v) x+1, y+1/2, z+1/2.
 

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