Crystal structures of five halido gold complexes involving piperidine or pyrrolidine as ligands or (protonated) as cations

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

Key indicators

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.019 Å
• Disorder in main residue
• R factor = 0.051
• wR factor = 0.130
• Data-to-parameter ratio = 23.1

Structure: 3

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.017
• wR factor = 0.030
• Data-to-parameter ratio = 29.7

Structure: 4

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.020 Å
• R factor = 0.041
• wR factor = 0.067
• Data-to-parameter ratio = 40.4

Structure: 6

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.034
• wR factor = 0.065
• Data-to-parameter ratio = 30.6

Structure: 7

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.024
• wR factor = 0.039
• Data-to-parameter ratio = 33.7

Computing details

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)

Crystal data

[AuBr(C4H9N)]·[Au(C4H9N)2]Br	Dx = 2.840 Mg m^−3
Mr = 767.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7080 reflections
a = 14.8040 (11) Å	θ = 2.5–29.3°
b = 12.4631 (6) Å	µ = 20.78 mm^−1
c = 19.4486 (8) Å	T = 100 K
V = 3588.3 (3) Å^3	Plate, colourless
Z = 8	0.08 × 0.08 × 0.01 mm
F(000) = 2784

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	4461 independent reflections
Radiation source: fine-focus sealed tube	3055 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.143
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	h = −19→19
Tmin = 0.287, Tmax = 0.819	k = −16→16
129826 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: mixed
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 57.3562P] where P = (Fo^2 + 2Fc^2)/3
4461 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 7.82 e Å^−3
90 restraints	Δρmin = −2.45 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Au1	0.22755 (3)	0.62223 (3)	0.35070 (2)	0.01738 (12)
Au2	0.24402 (3)	0.37177 (3)	0.36733 (2)	0.02106 (13)
Br1	0.24081 (9)	0.62289 (10)	0.47285 (6)	0.0319 (3)
Br2	0.47574 (7)	0.62096 (9)	0.29066 (7)	0.0265 (3)
N11	0.2072 (6)	0.6225 (7)	0.2457 (5)	0.0198 (18)
H01	0.154 (5)	0.613 (8)	0.238 (5)	0.00 (3)*
C12	0.2422 (9)	0.7142 (9)	0.2053 (6)	0.024 (3)
H12A	0.306033	0.728819	0.217289	0.029*
H12B	0.206137	0.779540	0.214322	0.029*
C13	0.2342 (13)	0.6814 (11)	0.1315 (7)	0.051 (4)
H13A	0.285701	0.709593	0.104528	0.061*
H13B	0.177388	0.709107	0.111426	0.061*
C14	0.2346 (11)	0.5599 (10)	0.1315 (7)	0.042 (4)
H14A	0.178228	0.531639	0.110969	0.051*
H14B	0.286700	0.532125	0.105008	0.051*
C15	0.2417 (10)	0.5284 (9)	0.2057 (7)	0.030 (4)
H15A	0.204779	0.463819	0.215090	0.036*
H15B	0.305281	0.512831	0.218052	0.036*
N21	0.3785 (7)	0.3993 (7)	0.3701 (5)	0.026 (2)
H02	0.396 (7)	0.459 (7)	0.359 (6)	0.01 (3)*
C22	0.4148 (9)	0.3975 (12)	0.4418 (6)	0.040 (3)
H22A	0.397647	0.330468	0.465778	0.047*
H22B	0.392387	0.459598	0.468609	0.047*
C23	0.5151 (9)	0.4038 (11)	0.4319 (8)	0.046 (4)
H23A	0.547490	0.373081	0.471874	0.055*
H23B	0.534842	0.479034	0.425349	0.055*
C24	0.5321 (8)	0.3377 (11)	0.3674 (8)	0.046 (4)
H24A	0.575759	0.374322	0.336788	0.056*
H24B	0.556329	0.266040	0.379409	0.056*
C25	0.4417 (8)	0.3276 (11)	0.3330 (7)	0.038 (3)
H25A	0.446156	0.348998	0.284058	0.046*
H25B	0.420235	0.252415	0.335148	0.046*
N31	0.1091 (8)	0.3412 (8)	0.3728 (6)	0.033 (2)
H03	0.105 (11)	0.278 (7)	0.362 (8)	0.05 (5)*
C32	0.0779 (10)	0.3300 (13)	0.4453 (7)	0.050 (3)
H32A	0.094769	0.259062	0.464201	0.060*	0.64 (2)
H32B	0.104374	0.386778	0.474678	0.060*	0.64 (2)
H32C	0.028784	0.276281	0.448143	0.060*	0.36 (2)
H32D	0.128372	0.305867	0.474869	0.060*	0.36 (2)
C33	−0.0217 (12)	0.341 (2)	0.4413 (11)	0.051 (6)	0.64 (2)
H33A	−0.044827	0.379924	0.482176	0.061*	0.64 (2)
H33B	−0.050730	0.269918	0.439248	0.061*	0.64 (2)
C34	−0.0420 (11)	0.404 (2)	0.3768 (13)	0.058 (8)	0.64 (2)
H34A	−0.083197	0.363328	0.346441	0.070*	0.64 (2)
H34B	−0.070657	0.473716	0.388309	0.070*	0.64 (2)
C35	0.0453 (8)	0.4212 (10)	0.3433 (7)	0.032 (3)
H35A	0.067222	0.494943	0.352072	0.039*	0.64 (2)
H35B	0.039676	0.410829	0.293019	0.039*	0.64 (2)
H35C	−0.006657	0.384712	0.321348	0.039*	0.36 (2)
H35D	0.075975	0.466200	0.308490	0.039*	0.36 (2)
C33'	0.045 (4)	0.435 (3)	0.4683 (12)	0.072 (17)*	0.36 (2)
H33C	0.094119	0.476047	0.490651	0.087*	0.36 (2)
H33D	−0.005492	0.426470	0.501145	0.087*	0.36 (2)
C34'	0.014 (2)	0.488 (2)	0.4031 (12)	0.035 (10)*	0.36 (2)
H34C	−0.052331	0.494791	0.402725	0.042*	0.36 (2)
H34D	0.040500	0.561337	0.399837	0.042*	0.36 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0260 (2)	0.01228 (19)	0.0139 (2)	0.00333 (18)	−0.00074 (14)	−0.00077 (16)
Au2	0.0371 (3)	0.0123 (2)	0.0138 (2)	0.00283 (16)	−0.00284 (15)	−0.0012 (2)
Br1	0.0612 (8)	0.0222 (6)	0.0122 (6)	0.0090 (6)	−0.0032 (5)	−0.0016 (5)
Br2	0.0183 (5)	0.0201 (5)	0.0410 (7)	0.0001 (5)	0.0013 (4)	0.0055 (5)
N11	0.018 (4)	0.017 (4)	0.024 (5)	−0.003 (4)	0.003 (4)	−0.003 (4)
C12	0.030 (8)	0.024 (6)	0.017 (8)	−0.007 (5)	−0.005 (5)	−0.001 (5)
C13	0.076 (12)	0.058 (10)	0.020 (9)	−0.018 (9)	−0.007 (8)	0.000 (8)
C14	0.062 (10)	0.047 (9)	0.018 (8)	0.020 (7)	−0.004 (7)	−0.015 (7)
C15	0.042 (9)	0.027 (6)	0.021 (9)	0.013 (5)	0.004 (5)	−0.004 (6)
N21	0.045 (6)	0.009 (4)	0.023 (6)	0.001 (4)	−0.011 (5)	0.000 (4)
C22	0.051 (9)	0.048 (8)	0.019 (7)	0.013 (7)	−0.020 (6)	−0.009 (6)
C23	0.037 (8)	0.039 (8)	0.063 (11)	0.006 (6)	−0.026 (7)	0.004 (7)
C24	0.029 (7)	0.032 (7)	0.078 (13)	0.004 (6)	−0.008 (8)	−0.014 (8)
C25	0.031 (7)	0.038 (7)	0.045 (9)	−0.006 (6)	0.008 (6)	−0.014 (6)
N31	0.047 (6)	0.024 (5)	0.027 (5)	0.007 (5)	0.006 (5)	0.001 (5)
C32	0.048 (5)	0.061 (5)	0.042 (5)	0.009 (4)	0.005 (4)	0.008 (4)
C33	0.041 (8)	0.064 (16)	0.048 (13)	0.003 (10)	0.012 (8)	0.021 (11)
C34	0.033 (8)	0.073 (18)	0.069 (16)	0.001 (10)	0.010 (9)	0.040 (14)
C35	0.037 (7)	0.028 (6)	0.033 (7)	0.001 (5)	−0.004 (5)	0.003 (5)

Geometric parameters (Å, º)

Au1—N11	2.065 (9)	C24—H24A	0.9900
Au1—Br1	2.3837 (12)	C24—H24B	0.9900
Au1—Au2	3.1476 (6)	C25—H25A	0.9900
Au1—Au2^i	3.1551 (6)	C25—H25B	0.9900
Au2—N21	2.021 (11)	N31—C35	1.488 (13)
Au2—N31	2.036 (12)	N31—C32	1.490 (14)
N11—C12	1.480 (12)	N31—H03	0.81 (7)
N11—C15	1.497 (12)	C32—C33'	1.460 (19)
N11—H01	0.81 (7)	C32—C33	1.483 (17)
C12—C13	1.496 (16)	C32—H32A	0.9900
C12—H12A	0.9900	C32—H32B	0.9900
C12—H12B	0.9900	C32—H32C	0.9900
C13—C14	1.514 (17)	C32—H32D	0.9900
C13—H13A	0.9900	C33—C34	1.508 (19)
C13—H13B	0.9900	C33—H33A	0.9900
C14—C15	1.500 (16)	C33—H33B	0.9900
C14—H14A	0.9900	C34—C35	1.463 (17)
C14—H14B	0.9900	C34—H34A	0.9900
C15—H15A	0.9900	C34—H34B	0.9900
C15—H15B	0.9900	C35—C34'	1.504 (18)
N21—C25	1.481 (13)	C35—H35A	0.9900
N21—C22	1.496 (12)	C35—H35B	0.9900
N21—H02	0.81 (7)	C35—H35C	0.9900
C22—C23	1.500 (15)	C35—H35D	0.9900
C22—H22A	0.9900	C33'—C34'	1.51 (2)
C22—H22B	0.9900	C33'—H33C	0.9900
C23—C24	1.523 (17)	C33'—H33D	0.9900
C23—H23A	0.9900	C34'—H34C	0.9900
C23—H23B	0.9900	C34'—H34D	0.9900
C24—C25	1.501 (15)
N11—Au1—Br1	176.3 (3)	C25—C24—H24B	110.7
N11—Au1—Au2	96.6 (2)	C23—C24—H24B	110.7
Br1—Au1—Au2	83.95 (3)	H24A—C24—H24B	108.8
N11—Au1—Au2^i	96.8 (2)	N21—C25—C24	107.2 (9)
Br1—Au1—Au2^i	83.31 (3)	N21—C25—H25A	110.3
Au2—Au1—Au2^i	163.074 (19)	C24—C25—H25A	110.3
N21—Au2—N31	175.4 (4)	N21—C25—H25B	110.3
N21—Au2—Au1	84.9 (2)	C24—C25—H25B	110.3
N31—Au2—Au1	96.6 (3)	H25A—C25—H25B	108.5
N21—Au2—Au1^ii	92.2 (2)	C35—N31—C32	103.3 (9)
N31—Au2—Au1^ii	87.2 (3)	C35—N31—Au2	118.5 (8)
Au1—Au2—Au1^ii	167.78 (2)	C32—N31—Au2	111.8 (9)
C12—N11—C15	102.1 (8)	C35—N31—H03	119 (10)
C12—N11—Au1	118.3 (7)	C32—N31—H03	98 (10)
C15—N11—Au1	117.5 (7)	Au2—N31—H03	104 (10)
C12—N11—H01	111 (7)	C33'—C32—N31	108.0 (14)
C15—N11—H01	97 (7)	C33—C32—N31	104.4 (11)
Au1—N11—H01	109 (8)	C33—C32—H32A	110.9
N11—C12—C13	105.7 (9)	N31—C32—H32A	110.9
N11—C12—H12A	110.6	C33—C32—H32B	110.9
C13—C12—H12A	110.6	N31—C32—H32B	110.9
N11—C12—H12B	110.6	H32A—C32—H32B	108.9
C13—C12—H12B	110.6	C33'—C32—H32C	110.1
H12A—C12—H12B	108.7	N31—C32—H32C	110.1
C12—C13—C14	105.9 (11)	C33'—C32—H32D	110.1
C12—C13—H13A	110.6	N31—C32—H32D	110.1
C14—C13—H13A	110.6	H32C—C32—H32D	108.4
C12—C13—H13B	110.6	C32—C33—C34	107.0 (13)
C14—C13—H13B	110.6	C32—C33—H33A	110.3
H13A—C13—H13B	108.7	C34—C33—H33A	110.3
C15—C14—C13	105.2 (10)	C32—C33—H33B	110.3
C15—C14—H14A	110.7	C34—C33—H33B	110.3
C13—C14—H14A	110.7	H33A—C33—H33B	108.6
C15—C14—H14B	110.7	C35—C34—C33	105.6 (12)
C13—C14—H14B	110.7	C35—C34—H34A	110.6
H14A—C14—H14B	108.8	C33—C34—H34A	110.6
N11—C15—C14	105.7 (9)	C35—C34—H34B	110.6
N11—C15—H15A	110.6	C33—C34—H34B	110.6
C14—C15—H15A	110.6	H34A—C34—H34B	108.7
N11—C15—H15B	110.6	C34—C35—N31	107.0 (11)
C14—C15—H15B	110.6	N31—C35—C34'	105.6 (12)
H15A—C15—H15B	108.7	C34—C35—H35A	110.3
C25—N21—C22	102.6 (9)	N31—C35—H35A	110.3
C25—N21—Au2	120.5 (7)	C34—C35—H35B	110.3
C22—N21—Au2	112.1 (8)	N31—C35—H35B	110.3
C25—N21—H02	103 (8)	H35A—C35—H35B	108.6
C22—N21—H02	98 (8)	N31—C35—H35C	110.6
Au2—N21—H02	117 (8)	C34'—C35—H35C	110.6
N21—C22—C23	103.6 (10)	N31—C35—H35D	110.6
N21—C22—H22A	111.0	C34'—C35—H35D	110.6
C23—C22—H22A	111.0	H35C—C35—H35D	108.8
N21—C22—H22B	111.0	C32—C33'—C34'	103.8 (15)
C23—C22—H22B	111.0	C32—C33'—H33C	111.0
H22A—C22—H22B	109.0	C34'—C33'—H33C	111.0
C22—C23—C24	103.9 (10)	C32—C33'—H33D	111.0
C22—C23—H23A	111.0	C34'—C33'—H33D	111.0
C24—C23—H23A	111.0	H33C—C33'—H33D	109.0
C22—C23—H23B	111.0	C35—C34'—C33'	108.1 (14)
C24—C23—H23B	111.0	C35—C34'—H34C	110.1
H23A—C23—H23B	109.0	C33'—C34'—H34C	110.1
C25—C24—C23	105.4 (10)	C35—C34'—H34D	110.1
C25—C24—H24A	110.7	C33'—C34'—H34D	110.1
C23—C24—H24A	110.7	H34C—C34'—H34D	108.4
N11—Au1—Au2—N21	100.5 (4)	Au2—N21—C22—C23	172.4 (8)
Br1—Au1—Au2—N21	−83.2 (3)	N21—C22—C23—C24	−36.5 (14)
Au2^i—Au1—Au2—N21	−41.9 (3)	C22—C23—C24—C25	17.2 (16)
N11—Au1—Au2—N31	−83.9 (4)	C22—N21—C25—C24	−31.0 (14)
Br1—Au1—Au2—N31	92.4 (3)	Au2—N21—C25—C24	−156.3 (9)
Au2^i—Au1—Au2—N31	133.7 (3)	C23—C24—C25—N21	8.6 (16)
N11—Au1—Au2—Au1^ii	23.8 (3)	Au1—Au2—N31—C35	22.3 (9)
Br1—Au1—Au2—Au1^ii	−159.83 (9)	Au1^ii—Au2—N31—C35	−146.0 (9)
Au2^i—Au1—Au2—Au1^ii	−118.48 (12)	Au1—Au2—N31—C32	−97.7 (8)
Au2—Au1—N11—C12	−147.6 (8)	Au1^ii—Au2—N31—C32	94.0 (8)
Au2^i—Au1—N11—C12	22.1 (8)	C35—N31—C32—C33'	−35 (2)
Au2—Au1—N11—C15	−24.3 (8)	Au2—N31—C32—C33'	94 (2)
Au2^i—Au1—N11—C15	145.4 (8)	C35—N31—C32—C33	34.9 (16)
C15—N11—C12—C13	38.1 (13)	Au2—N31—C32—C33	163.4 (13)
Au1—N11—C12—C13	168.8 (9)	N31—C32—C33—C34	−24 (2)
N11—C12—C13—C14	−24.3 (17)	C32—C33—C34—C35	4 (3)
C12—C13—C14—C15	0.7 (19)	C33—C34—C35—N31	19 (3)
C12—N11—C15—C14	−37.7 (13)	C32—N31—C35—C34	−33.4 (18)
Au1—N11—C15—C14	−169.0 (9)	Au2—N31—C35—C34	−157.7 (15)
C13—C14—C15—N11	22.9 (17)	C32—N31—C35—C34'	27.0 (19)
Au1—Au2—N21—C25	−138.4 (9)	Au2—N31—C35—C34'	−97.3 (18)
Au1^ii—Au2—N21—C25	29.7 (9)	N31—C32—C33'—C34'	28 (4)
Au1—Au2—N21—C22	100.7 (7)	N31—C35—C34'—C33'	−11 (4)
Au1^ii—Au2—N21—C22	−91.2 (7)	C32—C33'—C34'—C35	−10 (4)
C25—N21—C22—C23	41.7 (13)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Br2^iii	0.81 (7)	2.70 (7)	3.498 (9)	169 (9)
N21—H02···Br2	0.81 (7)	2.69 (8)	3.477 (10)	162 (11)
C22—H22B···Br1	0.99	3.03	3.859 (13)	142
N31—H03···Br2^ii	0.81 (7)	2.68 (10)	3.416 (12)	151 (14)
C32—H32A···Br1^ii	0.99	2.97	3.763 (14)	138
C33—H33A···Br1^iv	0.99	3.03	3.675 (18)	124

Symmetry codes: (ii) −x+1/2, y−1/2, z; (iii) x−1/2, y, −z+1/2; (iv) −x, −y+1, −z+1.

Trichlorido(piperidine-κN)gold(III) (3)

Crystal data

[AuCl3(C5H11N)]	F(000) = 712
Mr = 388.46	Dx = 2.729 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.47646 (16) Å	Cell parameters from 13188 reflections
b = 6.57436 (11) Å	θ = 2.4–30.7°
c = 16.9961 (3) Å	µ = 16.34 mm^−1
β = 93.5133 (16)°	T = 100 K
V = 945.36 (3) Å^3	Irregular, yellow
Z = 4	0.17 × 0.17 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	2853 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2690 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.037
ω scan	θmax = 31.1°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	h = −12→12
Tmin = 0.689, Tmax = 1.000	k = −9→9
24604 measured reflections	l = −23→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.017	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.030	w = 1/[σ^2(Fo^2) + (0.0085P)^2 + 0.3159P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.003
2853 reflections	Δρmax = 0.92 e Å^−3
96 parameters	Δρmin = −0.80 e Å^−3
0 restraints	Extinction correction: SHELXL2018/3 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00109 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.50340 (2)	0.60493 (2)	0.86802 (2)	0.00923 (4)
Cl1	0.28810 (7)	0.81001 (9)	0.87943 (4)	0.01663 (12)
Cl2	0.62533 (7)	0.74686 (9)	0.97772 (3)	0.01580 (12)
Cl3	0.38860 (7)	0.46665 (9)	0.75544 (3)	0.01487 (12)
N11	0.6977 (2)	0.4215 (3)	0.85214 (12)	0.0099 (4)
H01	0.659 (3)	0.348 (4)	0.8139 (18)	0.023 (8)*
C12	0.7391 (3)	0.2837 (4)	0.92065 (15)	0.0162 (5)
H12A	0.647301	0.196029	0.930291	0.019*
H12B	0.763017	0.366729	0.968501	0.019*
C13	0.8809 (3)	0.1509 (4)	0.90554 (16)	0.0169 (5)
H13A	0.851842	0.054401	0.862344	0.020*
H13B	0.910481	0.070664	0.953489	0.020*
C14	1.0226 (3)	0.2774 (4)	0.88339 (15)	0.0190 (6)
H14A	1.059299	0.364332	0.928430	0.023*
H14B	1.110477	0.186397	0.870636	0.023*
C15	0.9751 (3)	0.4096 (4)	0.81249 (16)	0.0174 (5)
H15A	0.946403	0.321752	0.766522	0.021*
H15B	1.065906	0.495127	0.799304	0.021*
C16	0.8357 (3)	0.5454 (4)	0.82901 (15)	0.0145 (5)
H16A	0.867252	0.641410	0.872008	0.017*
H16B	0.804704	0.625874	0.781317	0.017*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.00840 (5)	0.00890 (5)	0.01038 (5)	0.00117 (3)	0.00037 (3)	0.00010 (3)
Cl1	0.0149 (3)	0.0182 (3)	0.0168 (3)	0.0078 (2)	0.0008 (2)	−0.0010 (2)
Cl2	0.0155 (3)	0.0165 (3)	0.0150 (3)	0.0008 (2)	−0.0019 (2)	−0.0042 (2)
Cl3	0.0127 (3)	0.0159 (3)	0.0155 (3)	0.0016 (2)	−0.0026 (2)	−0.0045 (2)
N11	0.0087 (10)	0.0085 (10)	0.0123 (10)	0.0009 (8)	−0.0009 (8)	−0.0002 (7)
C12	0.0169 (13)	0.0133 (12)	0.0186 (13)	0.0035 (10)	0.0032 (10)	0.0064 (10)
C13	0.0158 (13)	0.0142 (12)	0.0202 (13)	0.0056 (10)	−0.0026 (10)	0.0019 (10)
C14	0.0120 (13)	0.0178 (13)	0.0266 (14)	0.0045 (10)	−0.0031 (11)	−0.0023 (11)
C15	0.0098 (12)	0.0177 (13)	0.0250 (14)	0.0025 (10)	0.0039 (10)	0.0011 (10)
C16	0.0113 (12)	0.0114 (11)	0.0214 (13)	0.0012 (10)	0.0053 (10)	0.0029 (10)

Geometric parameters (Å, º)

Au1—N11	2.0718 (19)	C12—H12A	0.9900
Au1—Cl2	2.2757 (6)	C12—H12B	0.9900
Au1—Cl3	2.2817 (6)	C13—H13A	0.9900
Au1—Cl1	2.2868 (6)	C13—H13B	0.9900
N11—C16	1.498 (3)	C14—H14A	0.9900
N11—C12	1.500 (3)	C14—H14B	0.9900
C12—C13	1.520 (3)	C15—H15A	0.9900
C13—C14	1.527 (4)	C15—H15B	0.9900
C14—C15	1.520 (4)	C16—H16A	0.9900
C15—C16	1.520 (3)	C16—H16B	0.9900
N11—H01	0.86 (3)
N11—Au1—Cl2	91.19 (6)	H12A—C12—H12B	108.0
N11—Au1—Cl3	87.73 (6)	C12—C13—H13A	109.3
Cl2—Au1—Cl3	177.91 (2)	C14—C13—H13A	109.3
N11—Au1—Cl1	177.36 (6)	C12—C13—H13B	109.3
Cl2—Au1—Cl1	90.77 (2)	C14—C13—H13B	109.3
Cl3—Au1—Cl1	90.25 (2)	H13A—C13—H13B	107.9
C16—N11—C12	112.49 (19)	C15—C14—H14A	109.8
C16—N11—Au1	110.96 (14)	C13—C14—H14A	109.8
C12—N11—Au1	113.61 (15)	C15—C14—H14B	109.8
N11—C12—C13	111.5 (2)	C13—C14—H14B	109.8
C12—C13—C14	111.8 (2)	H14A—C14—H14B	108.2
C15—C14—C13	109.4 (2)	C14—C15—H15A	109.4
C14—C15—C16	111.1 (2)	C16—C15—H15A	109.4
N11—C16—C15	110.96 (19)	C14—C15—H15B	109.4
C16—N11—H01	112 (2)	C16—C15—H15B	109.4
C12—N11—H01	108 (2)	H15A—C15—H15B	108.0
Au1—N11—H01	99 (2)	N11—C16—H16A	109.4
N11—C12—H12A	109.3	C15—C16—H16A	109.4
C13—C12—H12A	109.3	N11—C16—H16B	109.4
N11—C12—H12B	109.3	C15—C16—H16B	109.4
C13—C12—H12B	109.3	H16A—C16—H16B	108.0
C16—N11—C12—C13	−53.6 (3)	C13—C14—C15—C16	57.1 (3)
Au1—N11—C12—C13	179.30 (16)	C12—N11—C16—C15	54.9 (3)
N11—C12—C13—C14	54.2 (3)	Au1—N11—C16—C15	−176.54 (17)
C12—C13—C14—C15	−55.8 (3)	C14—C15—C16—N11	−57.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Cl3	0.86 (3)	2.57 (3)	3.021 (2)	114 (2)
N11—H01···Cl3^i	0.86 (3)	2.79 (3)	3.558 (2)	150 (3)
C12—H12B···Cl1^ii	0.99	2.89	3.475 (3)	119
C14—H14B···Cl1^iii	0.99	2.90	3.812 (3)	154
C12—H12A···Cl2^ii	0.99	2.89	3.636 (3)	133
C13—H13A···Cl3^i	0.99	2.83	3.661 (3)	142
C15—H15B···Cl3^iv	0.99	2.88	3.713 (3)	142
C16—H16B···Cl3^v	0.99	2.82	3.607 (2)	137

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) x+1, y−1, z; (iv) x+1, y, z; (v) −x+1, y+1/2, −z+3/2.

Bis(piperidinium) tetrachloridoaurate(III) chloride (4)

Crystal data

(C5H12N)2[AuCl4]Cl	Dx = 1.998 Mg m^−3
Mr = 546.53	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Iba2	Cell parameters from 2523 reflections
a = 19.4014 (15) Å	θ = 3.0–24.5°
b = 9.7612 (6) Å	µ = 8.82 mm^−1
c = 19.1922 (11) Å	T = 100 K
V = 3634.6 (4) Å^3	Plate, yellow
Z = 8	0.10 × 0.05 × 0.03 mm
F(000) = 2096

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	4242 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2632 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.075
ω scan	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	h = −24→25
Tmin = 0.718, Tmax = 1.000	k = −12→12
19554 measured reflections	l = −25→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0131P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4242 reflections	Δρmax = 0.84 e Å^−3
105 parameters	Δρmin = −0.86 e Å^−3
59 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.45 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.15024 (2)	0.74808 (5)	0.5000 (4)	0.01752 (11)
Cl1	0.23809 (15)	0.9043 (3)	0.5022 (7)	0.0293 (7)
Cl2	0.1479 (5)	0.7502 (5)	0.3813 (3)	0.041 (4)
Cl3	0.06697 (15)	0.5852 (3)	0.5004 (8)	0.0363 (8)
Cl4	0.1459 (5)	0.7478 (6)	0.6189 (2)	0.041 (4)
Cl5	0.500000	0.500000	0.7497 (9)	0.0209 (8)
Cl6	0.500000	0.500000	0.4997 (9)	0.0212 (8)
N11	0.4450 (6)	0.6793 (10)	0.6243 (7)	0.019 (3)*
H11A	0.470289	0.655584	0.586253	0.023*
H11B	0.463181	0.635613	0.661943	0.023*
C12	0.3724 (9)	0.6341 (16)	0.6143 (9)	0.041 (5)*
H12A	0.371230	0.533700	0.606908	0.049*
H12B	0.353076	0.678608	0.572227	0.049*
C13	0.3277 (9)	0.6715 (13)	0.6786 (9)	0.032 (5)*
H13A	0.279477	0.641926	0.670841	0.038*
H13B	0.345430	0.623615	0.720410	0.038*
C14	0.3301 (7)	0.8260 (12)	0.6901 (9)	0.014 (4)*
H14A	0.307256	0.873104	0.650700	0.017*
H14B	0.304874	0.849496	0.733331	0.017*
C15	0.4040 (8)	0.8740 (15)	0.6958 (8)	0.028 (4)*
H15A	0.424040	0.837655	0.739549	0.033*
H15B	0.404483	0.975256	0.698961	0.033*
C16	0.4494 (7)	0.8302 (12)	0.6350 (8)	0.026 (4)*
H16A	0.434476	0.878041	0.592151	0.031*
H16B	0.497850	0.856231	0.644571	0.031*
N21	0.4104 (6)	0.6232 (10)	0.3780 (7)	0.024 (3)*
H22A	0.428402	0.583084	0.339287	0.028*
H22B	0.422809	0.571487	0.415422	0.028*
C22	0.3351 (7)	0.6233 (14)	0.3724 (9)	0.035 (4)*
H23A	0.314692	0.657301	0.416377	0.042*
H23B	0.318457	0.528585	0.364636	0.042*
C23	0.3127 (10)	0.7123 (14)	0.3134 (9)	0.052 (6)*
H24A	0.261699	0.715798	0.312386	0.062*
H24B	0.328482	0.671209	0.269046	0.062*
C24	0.3408 (8)	0.8578 (14)	0.3190 (11)	0.037 (5)*
H25A	0.327245	0.910784	0.277207	0.045*
H25B	0.320773	0.903412	0.360378	0.045*
C25	0.4187 (8)	0.8560 (14)	0.3252 (9)	0.033 (4)*
H26A	0.435924	0.949881	0.334072	0.040*
H26B	0.439282	0.823089	0.281000	0.040*
C26	0.4402 (8)	0.7603 (14)	0.3857 (8)	0.036 (4)*
H21A	0.491080	0.753018	0.386922	0.043*
H21B	0.424817	0.800577	0.430385	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01711 (19)	0.02022 (19)	0.01522 (17)	0.0008 (2)	−0.0003 (10)	0.0000 (6)
Cl1	0.0294 (18)	0.0271 (14)	0.0313 (16)	−0.0094 (12)	−0.006 (5)	0.000 (4)
Cl2	0.054 (10)	0.041 (6)	0.027 (7)	−0.015 (4)	0.005 (5)	−0.008 (3)
Cl3	0.0258 (19)	0.0326 (16)	0.0503 (18)	−0.0116 (13)	0.003 (6)	−0.012 (5)
Cl4	0.046 (9)	0.071 (8)	0.006 (5)	−0.003 (4)	0.004 (4)	0.003 (4)
Cl5	0.024 (2)	0.0228 (18)	0.0163 (17)	−0.003 (7)	0.000	0.000
Cl6	0.031 (2)	0.0233 (18)	0.0098 (16)	0.0116 (16)	0.000	0.000

Geometric parameters (Å, º)

Au1—Cl3	2.267 (3)	C13—H13A	0.9900
Au1—Cl2	2.278 (13)	C13—H13B	0.9900
Au1—Cl4	2.284 (11)	C14—H14A	0.9900
Au1—Cl1	2.287 (3)	C14—H14B	0.9900
N11—C12	1.489 (15)	C15—H15A	0.9900
N11—C16	1.490 (13)	C15—H15B	0.9900
C12—C13	1.553 (16)	C16—H16A	0.9900
C13—C14	1.525 (14)	C16—H16B	0.9900
C14—C15	1.514 (15)	N21—H22A	0.9100
C15—C16	1.523 (14)	N21—H22B	0.9100
N21—C22	1.465 (14)	C22—H23A	0.9900
N21—C26	1.466 (13)	C22—H23B	0.9900
C22—C23	1.491 (15)	C23—H24A	0.9900
C23—C24	1.526 (15)	C23—H24B	0.9900
C24—C25	1.517 (15)	C24—H25A	0.9900
C25—C26	1.547 (14)	C24—H25B	0.9900
N11—H11A	0.9100	C25—H26A	0.9900
N11—H11B	0.9100	C25—H26B	0.9900
C12—H12A	0.9900	C26—H21A	0.9900
C12—H12B	0.9900	C26—H21B	0.9900
Cl3—Au1—Cl2	89.8 (4)	C16—C15—H15A	108.8
Cl3—Au1—Cl4	88.2 (4)	C14—C15—H15B	108.8
Cl2—Au1—Cl4	176.70 (12)	C16—C15—H15B	108.8
Cl3—Au1—Cl1	177.0 (3)	H15A—C15—H15B	107.7
Cl2—Au1—Cl1	91.6 (3)	N11—C16—H16A	109.6
Cl4—Au1—Cl1	90.6 (4)	C15—C16—H16A	109.6
C12—N11—C16	111.5 (11)	N11—C16—H16B	109.6
N11—C12—C13	110.8 (12)	C15—C16—H16B	109.6
C14—C13—C12	109.3 (11)	H16A—C16—H16B	108.1
C15—C14—C13	110.2 (12)	C22—N21—H22A	108.8
C14—C15—C16	113.9 (11)	C26—N21—H22A	108.8
N11—C16—C15	110.5 (10)	C22—N21—H22B	108.8
C22—N21—C26	113.6 (10)	C26—N21—H22B	108.8
N21—C22—C23	110.3 (12)	H22A—N21—H22B	107.7
C22—C23—C24	112.7 (12)	N21—C22—H23A	109.6
C25—C24—C23	110.6 (12)	C23—C22—H23A	109.6
C24—C25—C26	109.5 (12)	N21—C22—H23B	109.6
N21—C26—C25	111.7 (11)	C23—C22—H23B	109.6
C12—N11—H11A	109.3	H23A—C22—H23B	108.1
C16—N11—H11A	109.3	C22—C23—H24A	109.1
C12—N11—H11B	109.3	C24—C23—H24A	109.1
C16—N11—H11B	109.3	C22—C23—H24B	109.1
H11A—N11—H11B	108.0	C24—C23—H24B	109.1
N11—C12—H12A	109.5	H24A—C23—H24B	107.8
C13—C12—H12A	109.5	C25—C24—H25A	109.5
N11—C12—H12B	109.5	C23—C24—H25A	109.5
C13—C12—H12B	109.5	C25—C24—H25B	109.5
H12A—C12—H12B	108.1	C23—C24—H25B	109.5
C14—C13—H13A	109.8	H25A—C24—H25B	108.1
C12—C13—H13A	109.8	C24—C25—H26A	109.8
C14—C13—H13B	109.8	C26—C25—H26A	109.8
C12—C13—H13B	109.8	C24—C25—H26B	109.8
H13A—C13—H13B	108.3	C26—C25—H26B	109.8
C15—C14—H14A	109.6	H26A—C25—H26B	108.2
C13—C14—H14A	109.6	N21—C26—H21A	109.3
C15—C14—H14B	109.6	C25—C26—H21A	109.3
C13—C14—H14B	109.6	N21—C26—H21B	109.3
H14A—C14—H14B	108.1	C25—C26—H21B	109.3
C14—C15—H15A	108.8	H21A—C26—H21B	107.9
C16—N11—C12—C13	−59.6 (17)	C26—N21—C22—C23	56.0 (16)
N11—C12—C13—C14	58.7 (17)	N21—C22—C23—C24	−55.1 (18)
C12—C13—C14—C15	−54.6 (17)	C22—C23—C24—C25	55 (2)
C13—C14—C15—C16	53.4 (16)	C23—C24—C25—C26	−53.1 (18)
C12—N11—C16—C15	55.6 (16)	C22—N21—C26—C25	−56.3 (16)
C14—C15—C16—N11	−53.2 (16)	C24—C25—C26—N21	54.1 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···Cl6	0.91	2.32	3.150 (16)	151
N11—H11B···Cl5	0.91	2.26	3.161 (16)	172
C12—H12A···Cl4^i	0.99	2.82	3.788 (17)	166
C13—H13A···Cl4	0.99	2.96	3.78 (2)	141
C16—H16A···Cl3^ii	0.99	2.68	3.601 (16)	155
N21—H22B···Cl6	0.91	2.31	3.150 (15)	153
N21—H22A···Cl5^iii	0.91	2.35	3.246 (17)	166
C22—H23B···Cl2^i	0.99	2.81	3.661 (14)	144
C23—H24A···Cl2	0.99	2.60	3.47 (2)	148

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, z; (iii) x, −y+1, z−1/2.

Bis(pyrrolidinium) tetrabromidoaurate(III) bromide (6)

Crystal data

(C4H10N)2[AuBr4]Br	Dx = 2.880 Mg m^−3
Mr = 740.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Ibam	Cell parameters from 6924 reflections
a = 19.1275 (7) Å	θ = 2.4–30.3°
b = 9.4396 (13) Å	µ = 20.28 mm^−1
c = 18.9259 (17) Å	T = 100 K
V = 3417.2 (6) Å^3	Plate, red
Z = 8	0.15 × 0.12 × 0.03 mm
F(000) = 2688

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	2689 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
Detector resolution: 16.1419 pixels mm^-1	θmax = 31.0°, θmin = 2.1°
ω scan	h = −27→27
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	k = −12→13
Tmin = 0.177, Tmax = 1.000	l = −27→26
35669 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: mixed
wR(F^2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0204P)^2 + 17.1013P] where P = (Fo^2 + 2Fc^2)/3
2689 reflections	(Δ/σ)max = 0.001
88 parameters	Δρmax = 2.21 e Å^−3
1 restraint	Δρmin = −1.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.14803 (2)	0.71040 (3)	0.000000	0.01444 (7)
Br1	0.14858 (2)	0.71441 (5)	0.12839 (3)	0.02063 (12)
Br2	0.22029 (4)	0.49747 (8)	0.000000	0.02791 (18)
Br3	0.07792 (3)	0.92257 (7)	0.000000	0.02033 (15)
Br4	0.000000	0.500000	0.000000	0.01607 (19)
Br5	0.000000	0.500000	0.250000	0.0268 (2)
N11	0.0999 (2)	0.3577 (5)	0.1304 (3)	0.0271 (10)
H01	0.069 (3)	0.423 (6)	0.161 (3)	0.05 (2)*
H02	0.101 (3)	0.392 (7)	0.079 (2)	0.05 (2)*
C12	0.0578 (3)	0.2271 (5)	0.1206 (3)	0.0299 (13)
H12A	0.064538	0.187577	0.072666	0.036*
H12B	0.007466	0.246555	0.127932	0.036*
C13	0.0852 (3)	0.1262 (5)	0.1763 (3)	0.0248 (11)
H13A	0.076595	0.026327	0.162891	0.030*
H13B	0.063519	0.144850	0.222896	0.030*
C14	0.1628 (3)	0.1595 (5)	0.1772 (3)	0.0280 (13)
H14A	0.187067	0.112565	0.137389	0.034*
H14B	0.184447	0.128375	0.222131	0.034*
C15	0.1659 (3)	0.3205 (6)	0.1699 (4)	0.0316 (14)
H15A	0.166824	0.366671	0.216800	0.038*
H15B	0.207800	0.349832	0.142885	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01035 (12)	0.01443 (13)	0.01854 (14)	0.00078 (9)	0.000	0.000
Br1	0.0196 (2)	0.0233 (3)	0.0190 (3)	−0.00056 (19)	−0.00249 (19)	0.0003 (2)
Br2	0.0256 (4)	0.0281 (4)	0.0300 (4)	0.0144 (3)	0.000	0.000
Br3	0.0190 (3)	0.0160 (3)	0.0260 (4)	0.0047 (2)	0.000	0.000
Br4	0.0138 (4)	0.0170 (4)	0.0174 (5)	0.0002 (3)	0.000	0.000
Br5	0.0195 (5)	0.0433 (6)	0.0177 (5)	0.000	0.000	0.000
N11	0.023 (2)	0.030 (3)	0.028 (3)	0.005 (2)	−0.002 (2)	0.007 (2)
C12	0.033 (3)	0.021 (3)	0.036 (3)	−0.002 (2)	−0.012 (3)	−0.003 (2)
C13	0.031 (3)	0.017 (2)	0.027 (3)	−0.001 (2)	−0.001 (2)	0.005 (2)
C14	0.024 (3)	0.021 (3)	0.039 (3)	0.006 (2)	0.003 (2)	0.013 (3)
C15	0.016 (2)	0.032 (3)	0.046 (4)	−0.001 (2)	−0.002 (3)	0.012 (3)

Geometric parameters (Å, º)

Au1—Br3	2.4102 (7)	C12—H12B	0.9900
Au1—Br1	2.4303 (5)	C13—C14	1.517 (7)
Au1—Br1^i	2.4303 (5)	C13—H13A	0.9900
Au1—Br2	2.4393 (8)	C13—H13B	0.9900
N11—C12	1.484 (7)	C14—C15	1.527 (7)
N11—C15	1.508 (7)	C14—H14A	0.9900
N11—H01	1.03 (4)	C14—H14B	0.9900
N11—H02	1.02 (4)	C15—H15A	0.9900
C12—C13	1.514 (7)	C15—H15B	0.9900
C12—H12A	0.9900
Br3—Au1—Br1	89.399 (13)	C12—C13—C14	102.5 (4)
Br3—Au1—Br1^i	89.399 (13)	C12—C13—H13A	111.3
Br1—Au1—Br1^i	178.15 (3)	C14—C13—H13A	111.3
Br3—Au1—Br2	179.29 (3)	C12—C13—H13B	111.3
Br1—Au1—Br2	90.592 (13)	C14—C13—H13B	111.3
Br1^i—Au1—Br2	90.593 (13)	H13A—C13—H13B	109.2
C12—N11—C15	108.8 (4)	C13—C14—C15	104.1 (4)
C12—N11—H01	105 (4)	C13—C14—H14A	110.9
C15—N11—H01	110 (4)	C15—C14—H14A	110.9
C12—N11—H02	99 (4)	C13—C14—H14B	110.9
C15—N11—H02	122 (4)	C15—C14—H14B	110.9
H01—N11—H02	111 (5)	H14A—C14—H14B	109.0
N11—C12—C13	104.4 (4)	N11—C15—C14	104.2 (4)
N11—C12—H12A	110.9	N11—C15—H15A	110.9
C13—C12—H12A	110.9	C14—C15—H15A	110.9
N11—C12—H12B	110.9	N11—C15—H15B	110.9
C13—C12—H12B	110.9	C14—C15—H15B	110.9
H12A—C12—H12B	108.9	H15A—C15—H15B	108.9
C15—N11—C12—C13	20.1 (6)	C12—N11—C15—C14	4.5 (6)
N11—C12—C13—C14	−36.7 (6)	C13—C14—C15—N11	−27.3 (6)
C12—C13—C14—C15	39.7 (6)

Symmetry code: (i) x, y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Br5	1.03 (4)	2.26 (5)	3.253 (5)	161 (5)
N11—H02···Br2	1.02 (4)	2.90 (6)	3.624 (5)	128 (5)
N11—H02···Br4	1.02 (4)	2.65 (6)	3.398 (5)	130 (5)
C12—H12B···Br1^ii	0.99	3.01	3.989 (6)	171
C15—H15A···Br1^iii	0.99	3.05	3.847 (7)	139
C15—H15B···Br1^iv	0.99	3.04	3.770 (5)	131
C15—H15B···Br2	0.99	3.05	3.769 (6)	130
C12—H12A···Br3^v	0.99	2.87	3.691 (6)	141

Symmetry codes: (ii) −x, −y+1, z; (iii) x, −y+1, −z+1/2; (iv) −x+1/2, y−1/2, z; (v) x, y−1, z.

Tribromido(piperidine-κN)gold(III) dichloromethane monosolvate (7)

Crystal data

[AuBr3(C5H11N)]·CH2Cl2	F(000) = 1096
Mr = 606.77	Dx = 2.938 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3473 (3) Å	Cell parameters from 8200 reflections
b = 22.0860 (8) Å	θ = 2.7–30.8°
c = 8.5066 (3) Å	µ = 19.82 mm^−1
β = 96.423 (3)°	T = 100 K
V = 1371.71 (9) Å^3	Block, red
Z = 4	0.15 × 0.12 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	4139 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3658 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.043
ω scan	θmax = 30.9°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	h = −10→10
Tmin = 0.574, Tmax = 1.000	k = −31→31
36043 measured reflections	l = −12→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.039	w = 1/[σ^2(Fo^2) + (0.0061P)^2 + 2.1369P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.001
4139 reflections	Δρmax = 0.84 e Å^−3
123 parameters	Δρmin = −0.83 e Å^−3
0 restraints	Extinction correction: SHELXL2018/3 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00041 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.51277 (2)	0.24454 (2)	0.25555 (2)	0.00781 (4)
Br1	0.52418 (4)	0.35307 (2)	0.21990 (4)	0.01219 (7)
Br2	0.79078 (4)	0.24741 (2)	0.43841 (4)	0.01246 (7)
Br3	0.24299 (4)	0.24137 (2)	0.06300 (4)	0.01363 (7)
N11	0.5152 (4)	0.15094 (13)	0.2928 (3)	0.0105 (6)
H01	0.564 (5)	0.1462 (17)	0.388 (4)	0.010 (9)*
C12	0.3327 (5)	0.12067 (16)	0.2919 (4)	0.0166 (7)
H12A	0.262660	0.125337	0.186272	0.020*
H12B	0.262625	0.140485	0.370457	0.020*
C13	0.3548 (5)	0.05401 (17)	0.3310 (4)	0.0206 (8)
H13A	0.232656	0.034650	0.324584	0.025*
H13B	0.414508	0.049313	0.440558	0.025*
C14	0.4697 (5)	0.02288 (17)	0.2170 (4)	0.0219 (8)
H14A	0.488269	−0.020115	0.247579	0.026*
H14B	0.404673	0.024218	0.108612	0.026*
C15	0.6531 (5)	0.05400 (17)	0.2194 (4)	0.0212 (8)
H15A	0.724300	0.034610	0.141007	0.025*
H15B	0.722566	0.049134	0.325312	0.025*
C16	0.6307 (5)	0.12090 (16)	0.1816 (4)	0.0158 (7)
H16A	0.752587	0.140470	0.189969	0.019*
H16B	0.572596	0.125882	0.071625	0.019*
C1	0.0245 (5)	0.37793 (17)	0.2600 (4)	0.0185 (7)
H1A	0.145117	0.357439	0.273057	0.022*
H1B	−0.071860	0.346408	0.252639	0.022*
Cl1	0.00338 (15)	0.42462 (5)	0.42603 (12)	0.0294 (2)
Cl2	0.00380 (16)	0.42122 (5)	0.08506 (12)	0.0327 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.00905 (6)	0.00586 (6)	0.00833 (6)	−0.00023 (5)	0.00018 (4)	0.00005 (5)
Br1	0.01637 (16)	0.00648 (16)	0.01348 (16)	0.00051 (12)	0.00062 (12)	0.00047 (12)
Br2	0.01135 (14)	0.01168 (17)	0.01346 (15)	−0.00178 (12)	−0.00249 (11)	0.00151 (12)
Br3	0.01223 (15)	0.01432 (18)	0.01331 (15)	−0.00090 (13)	−0.00310 (12)	0.00090 (13)
N11	0.0165 (14)	0.0063 (14)	0.0080 (13)	0.0013 (11)	−0.0018 (11)	−0.0003 (10)
C12	0.0186 (18)	0.0109 (18)	0.0216 (18)	−0.0050 (14)	0.0082 (14)	−0.0023 (14)
C13	0.032 (2)	0.0105 (19)	0.0203 (18)	−0.0055 (15)	0.0068 (16)	−0.0003 (15)
C14	0.038 (2)	0.0085 (18)	0.0198 (19)	0.0001 (16)	0.0037 (17)	−0.0009 (14)
C15	0.031 (2)	0.0091 (19)	0.0233 (19)	0.0028 (15)	0.0042 (16)	−0.0017 (15)
C16	0.0212 (18)	0.0104 (18)	0.0162 (17)	0.0036 (14)	0.0038 (14)	0.0002 (14)
C1	0.0178 (18)	0.0147 (18)	0.0239 (19)	0.0012 (14)	0.0061 (15)	0.0030 (15)
Cl1	0.0363 (6)	0.0285 (6)	0.0232 (5)	0.0024 (4)	0.0023 (4)	−0.0021 (4)
Cl2	0.0477 (7)	0.0282 (6)	0.0239 (5)	0.0064 (5)	0.0118 (5)	0.0081 (4)

Geometric parameters (Å, º)

Au1—N11	2.091 (3)	C12—H12A	0.9900
Au1—Br1	2.4187 (4)	C12—H12B	0.9900
Au1—Br2	2.4260 (3)	C13—H13A	0.9900
Au1—Br3	2.4270 (3)	C13—H13B	0.9900
N11—C16	1.495 (4)	C14—H14A	0.9900
N11—C12	1.497 (4)	C14—H14B	0.9900
C12—C13	1.514 (5)	C15—H15A	0.9900
C13—C14	1.520 (5)	C15—H15B	0.9900
C14—C15	1.511 (5)	C16—H16A	0.9900
C15—C16	1.517 (5)	C16—H16B	0.9900
C1—Cl2	1.761 (4)	C1—H1A	0.9900
C1—Cl1	1.769 (4)	C1—H1B	0.9900
N11—H01	0.85 (4)
N11—Au1—Br1	177.24 (8)	C14—C13—H13A	109.5
N11—Au1—Br2	86.35 (8)	C12—C13—H13B	109.5
Br1—Au1—Br2	90.913 (12)	C14—C13—H13B	109.5
N11—Au1—Br3	93.80 (8)	H13A—C13—H13B	108.1
Br1—Au1—Br3	88.920 (12)	C15—C14—H14A	109.6
Br2—Au1—Br3	177.454 (13)	C13—C14—H14A	109.6
C16—N11—C12	111.7 (3)	C15—C14—H14B	109.6
C16—N11—Au1	109.8 (2)	C13—C14—H14B	109.6
C12—N11—Au1	116.6 (2)	H14A—C14—H14B	108.2
N11—C12—C13	111.1 (3)	C14—C15—H15A	109.4
C12—C13—C14	110.7 (3)	C16—C15—H15A	109.4
C15—C14—C13	110.1 (3)	C14—C15—H15B	109.4
C14—C15—C16	111.4 (3)	C16—C15—H15B	109.4
N11—C16—C15	110.7 (3)	H15A—C15—H15B	108.0
Cl2—C1—Cl1	110.5 (2)	N11—C16—H16A	109.5
C16—N11—H01	110 (2)	C15—C16—H16A	109.5
C12—N11—H01	104 (2)	N11—C16—H16B	109.5
Au1—N11—H01	105 (3)	C15—C16—H16B	109.5
N11—C12—H12A	109.4	H16A—C16—H16B	108.1
C13—C12—H12A	109.4	Cl2—C1—H1A	109.5
N11—C12—H12B	109.4	Cl1—C1—H1A	109.5
C13—C12—H12B	109.4	Cl2—C1—H1B	109.5
H12A—C12—H12B	108.0	Cl1—C1—H1B	109.5
C12—C13—H13A	109.5	H1A—C1—H1B	108.1
C16—N11—C12—C13	56.4 (4)	C13—C14—C15—C16	−56.3 (4)
Au1—N11—C12—C13	−176.2 (2)	C12—N11—C16—C15	−55.8 (4)
N11—C12—C13—C14	−56.4 (4)	Au1—N11—C16—C15	173.2 (2)
C12—C13—C14—C15	56.3 (4)	C14—C15—C16—N11	56.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Br1^i	0.85 (4)	2.87 (4)	3.627 (3)	148 (3)
C14—H14A···Br1^ii	0.99	2.82	3.788 (4)	167
C16—H16B···Br1^iii	0.99	3.01	3.960 (3)	161
C1—H1B···Br1^iv	0.99	2.95	3.695 (4)	133
C1—H1B···Br2^iv	0.99	2.94	3.761 (4)	141
C12—H12A···Cl1^iii	0.99	2.97	3.855 (4)	150
C15—H15B···Cl2^v	0.99	2.93	3.849 (4)	156
C1—H1A···Br1	0.99	2.87	3.765 (4)	150

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x−1, y, z; (v) x+1, −y+1/2, z+1/2.