Crystal structures of five gold(I) complexes with methyl­piperidine ligands

Five structures with methyl­piperidine ligands and gold(I) centres all exhibit linear geometry at the Au atom, and equatorial and axial positions, respectively, for the methyl groups and Au atoms at the piperidine rings. The packing involves hydrogen bonding and aurophilic inter­actions.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.048
• Data-to-parameter ratio = 27.4

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.029
• wR factor = 0.064
• Data-to-parameter ratio = 28.0

Structure: 3

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.023
• wR factor = 0.041
• Data-to-parameter ratio = 30.0

Structure: 4

• Single-crystal X-ray study
• T = 101 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.040
• wR factor = 0.070
• Data-to-parameter ratio = 25.3

Structure: 5

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.029
• wR factor = 0.049
• Data-to-parameter ratio = 29.3

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.256 Check
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.52Ang From Cl1            -1.51 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H22B      .      -0.31 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H16A     ..CL1      .       2.85 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H22B     ..AU1      .       2.80 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H23A     ..AU1      .       2.85 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
              H01     H02
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  2  0,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         28 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        4.1 Ratio
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0128 Ang.

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       9.04 Why ?
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13A     ..CL2      .       2.91 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
              H01     H02
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio
PLAT794_ALERT_5_G Tentative Bond Valency for Au2       (I)       .       0.98 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  0  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         69 Note
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 1-1 0)         Est.d BASF       0.30 Check
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          5 Note
                4 -4 12,  -2  4 11,  -3  5 11,   5 -2 10,   4  0  9,
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  16 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: 3


Alert level C
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........     Please Do !

Author Response: The cell is presented in a non-standard form (b < a) to facilitate comparison with the isotypic compound 2.

PLAT977_ALERT_2_C Check Negative Difference Density on H25B      .      -0.33 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H27A      .      -0.36 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13A     ..BR2      .       3.19 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
              H01     H02
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  0  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        324 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 4


Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.122
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0156 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
                1  0  0,   1  1  0,   2  0  0,  -1  1  1,   0  1  1,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
                0  2  0,   1  3  0,   3  1  0,   3  3  0,   5  1  0,   7  1  0,

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.122 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.02 Why ?
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H36B     ..AU1      .       2.87 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H66A     ..AU3      .       2.91 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H46B     ..AU4      .       2.75 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H34      ..CL1      .       2.86 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H36A     ..CL3      .       2.88 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H42B     ..CL3      .       2.95 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H37A     ..CL5      .       2.90 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H37B     ..CL6      .       2.94 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H67C     ..CL7      .       2.95 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15B     ..CL8      .       2.89 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H55B     ..CL8      .       2.94 Ang.
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          7 Note
              Cl
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         15 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 1 0 0)         Est.d BASF       0.46 Check
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          6 Note
                3  1  0,   5  1  0,   7  1  0,   1  3  0,   3  3  0,   0  2  0,

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  20 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 5


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.35 Report
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        7.7 Ratio
PLAT245_ALERT_2_C U(iso) H01       Smaller than U(eq) N11       by      0.015 Ang   2
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     13.402 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.916 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.79Ang From Au2             2.19 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.76Ang From Au1             1.63 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      14.30 Why ?
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H27A     ..CL1      .       2.92 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H17B     ..CL1      .       2.84 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H25B     ..CL1      .       2.96 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13A     ..AU1      .       3.01 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H15B     ..AU1      .       2.94 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H17C     ..AU1      .       2.85 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H23B     ..AU2      .       3.03 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H25A     ..AU2      .       2.94 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H27C     ..AU2      .       2.85 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
              H01     H02
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        219 Note
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  18 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  13 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Bis(4-methylpiperidine-κN)gold(I) chloride (1)

Crystal data

[Au(C6H13N)2]Cl	F(000) = 832
Mr = 430.76	Dx = 1.951 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.4068 (3) Å	Cell parameters from 8714 reflections
b = 25.2542 (15) Å	θ = 2.2–30.9°
c = 9.3395 (4) Å	µ = 10.19 mm^−1
β = 103.946 (4)°	T = 100 K
V = 1466.57 (12) Å^3	Lath, colourless
Z = 4	0.21 × 0.03 × 0.01 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	4248 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3650 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 16.1419 pixels mm^-1	θmax = 30.0°, θmin = 2.4°
ω scan	h = −9→8
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −35→35
Tmin = 0.398, Tmax = 1.000	l = −13→12
49187 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)] = 0.033	Hydrogen site location: mixed
wR(F^2) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0141P)^2 + 1.4591P] where P = (Fo^2 + 2Fc^2)/3
4248 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 1.13 e Å^−3
1 restraint	Δρmin = −1.57 e Å^−3

Special details

Geometry. Additional structural data:

Distance 5.9269 (0.0003) Au1 - Au1_$1

Angle 135.26 ( 1.44) H02 - Cl1 - H01_$1

Torsion angles 2.93 ( 0.32) C26 - N21 - N11 - C12 2.19 ( 0.31) C22 - N21 - N11 - C16

Operator for generating equivalent atoms: $1 -x, -y+1, -z+1

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

	x	y	z	Uiso*/Ueq
Au1	0.27850 (2)	0.58105 (2)	0.41086 (2)	0.01228 (4)
Cl1	0.07333 (15)	0.42372 (4)	0.25393 (10)	0.01992 (19)
N11	0.2215 (5)	0.63222 (12)	0.5676 (3)	0.0128 (6)
H01	0.139 (6)	0.6124 (15)	0.613 (4)	0.018 (11)*
C12	0.0986 (6)	0.68027 (15)	0.5052 (4)	0.0161 (8)
H12A	0.058954	0.700496	0.585531	0.019*
H12B	−0.035734	0.669534	0.434086	0.019*
C13	0.2293 (6)	0.71521 (14)	0.4282 (4)	0.0142 (7)
H13A	0.145689	0.747515	0.391848	0.017*
H13B	0.255772	0.696126	0.341629	0.017*
C14	0.4460 (6)	0.73133 (13)	0.5300 (4)	0.0132 (7)
H14	0.415702	0.754449	0.609509	0.016*
C15	0.5635 (6)	0.68186 (14)	0.6033 (4)	0.0140 (7)
H15A	0.609429	0.660305	0.527799	0.017*
H15B	0.694185	0.692767	0.677764	0.017*
C16	0.4233 (6)	0.64834 (14)	0.6774 (4)	0.0147 (7)
H16A	0.503518	0.616358	0.720715	0.018*
H16B	0.385848	0.668775	0.758154	0.018*
C17	0.5835 (7)	0.76300 (15)	0.4479 (4)	0.0220 (8)
H17A	0.719934	0.772491	0.516224	0.033*
H17B	0.506738	0.795302	0.407423	0.033*
H17C	0.612007	0.741537	0.367261	0.033*
N21	0.3334 (5)	0.52931 (12)	0.2545 (3)	0.0130 (6)
H02	0.263 (6)	0.4985 (13)	0.266 (4)	0.013 (10)*
C22	0.5644 (6)	0.51457 (15)	0.2782 (4)	0.0179 (8)
H22A	0.580427	0.486931	0.206434	0.021*
H22B	0.617710	0.499995	0.378789	0.021*
C23	0.6963 (6)	0.56314 (14)	0.2590 (4)	0.0153 (7)
H23A	0.848096	0.552454	0.270366	0.018*
H23B	0.691474	0.589011	0.337743	0.018*
C24	0.6152 (6)	0.58985 (13)	0.1087 (4)	0.0136 (7)
H24	0.644492	0.565394	0.031584	0.016*
C25	0.3730 (6)	0.59872 (14)	0.0763 (4)	0.0135 (7)
H25A	0.342750	0.627499	0.140439	0.016*
H25B	0.320515	0.610250	−0.027422	0.016*
C26	0.2515 (6)	0.54938 (14)	0.1015 (4)	0.0152 (7)
H26A	0.096396	0.557673	0.084466	0.018*
H26B	0.268389	0.521627	0.030228	0.018*
C27	0.7347 (7)	0.64190 (15)	0.0996 (5)	0.0230 (9)
H27A	0.692865	0.655692	−0.001365	0.035*
H27B	0.890107	0.635485	0.126803	0.035*
H27C	0.697421	0.667793	0.167558	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01176 (6)	0.01306 (6)	0.01248 (7)	−0.00121 (6)	0.00385 (4)	0.00032 (6)
Cl1	0.0163 (4)	0.0183 (5)	0.0256 (5)	−0.0030 (4)	0.0060 (4)	0.0074 (4)
N11	0.0093 (14)	0.0160 (15)	0.0139 (16)	−0.0032 (13)	0.0042 (12)	0.0016 (12)
C12	0.0098 (17)	0.0218 (19)	0.0162 (18)	0.0029 (15)	0.0022 (14)	−0.0013 (15)
C13	0.0143 (19)	0.0125 (17)	0.0146 (18)	0.0033 (14)	0.0009 (14)	0.0003 (14)
C14	0.0140 (18)	0.0106 (16)	0.0150 (17)	0.0010 (14)	0.0035 (14)	−0.0013 (13)
C15	0.0134 (18)	0.0145 (17)	0.0141 (18)	0.0020 (14)	0.0033 (14)	−0.0013 (14)
C16	0.0149 (18)	0.0167 (18)	0.0114 (17)	0.0015 (15)	0.0010 (14)	0.0011 (14)
C17	0.022 (2)	0.019 (2)	0.025 (2)	−0.0019 (17)	0.0065 (17)	−0.0006 (16)
N21	0.0144 (15)	0.0098 (14)	0.0162 (15)	−0.0034 (12)	0.0062 (12)	0.0018 (12)
C22	0.020 (2)	0.0163 (19)	0.0183 (19)	0.0056 (15)	0.0064 (16)	0.0030 (15)
C23	0.0125 (18)	0.0165 (17)	0.0168 (18)	0.0012 (14)	0.0032 (14)	0.0021 (14)
C24	0.0188 (19)	0.0071 (17)	0.0167 (17)	−0.0019 (14)	0.0077 (14)	−0.0024 (13)
C25	0.0154 (18)	0.0157 (17)	0.0089 (16)	−0.0015 (14)	0.0018 (14)	0.0024 (13)
C26	0.0126 (19)	0.0157 (17)	0.0162 (18)	−0.0006 (14)	0.0016 (15)	−0.0011 (15)
C27	0.024 (2)	0.0202 (19)	0.026 (2)	−0.0067 (18)	0.0080 (17)	0.0010 (18)

Geometric parameters (Å, º)

Au1—N11	2.051 (3)	C14—H14	1.0000
Au1—N21	2.052 (3)	C15—H15A	0.9900
N11—C12	1.487 (5)	C15—H15B	0.9900
N11—C16	1.499 (5)	C16—H16A	0.9900
C12—C13	1.513 (5)	C16—H16B	0.9900
C13—C14	1.536 (5)	C17—H17A	0.9800
C14—C17	1.526 (5)	C17—H17B	0.9800
C14—C15	1.532 (5)	C17—H17C	0.9800
C15—C16	1.517 (5)	N21—H02	0.92 (3)
N21—C26	1.488 (4)	C22—H22A	0.9900
N21—C22	1.490 (5)	C22—H22B	0.9900
C22—C23	1.524 (5)	C23—H23A	0.9900
C23—C24	1.531 (5)	C23—H23B	0.9900
C24—C25	1.524 (5)	C24—H24	1.0000
C24—C27	1.534 (5)	C25—H25A	0.9900
C25—C26	1.517 (5)	C25—H25B	0.9900
N11—H01	0.90 (3)	C26—H26A	0.9900
C12—H12A	0.9900	C26—H26B	0.9900
C12—H12B	0.9900	C27—H27A	0.9800
C13—H13A	0.9900	C27—H27B	0.9800
C13—H13B	0.9900	C27—H27C	0.9800
N11—Au1—N21	179.43 (12)	C15—C16—H16A	109.6
C12—N11—C16	109.5 (3)	N11—C16—H16B	109.6
C12—N11—Au1	113.8 (2)	C15—C16—H16B	109.6
C16—N11—Au1	112.8 (2)	H16A—C16—H16B	108.1
N11—C12—C13	111.2 (3)	C14—C17—H17A	109.5
C12—C13—C14	112.4 (3)	C14—C17—H17B	109.5
C17—C14—C15	111.8 (3)	H17A—C17—H17B	109.5
C17—C14—C13	111.9 (3)	C14—C17—H17C	109.5
C15—C14—C13	109.5 (3)	H17A—C17—H17C	109.5
C16—C15—C14	112.2 (3)	H17B—C17—H17C	109.5
N11—C16—C15	110.3 (3)	C26—N21—H02	109 (2)
C26—N21—C22	109.6 (3)	C22—N21—H02	106 (3)
C26—N21—Au1	112.7 (2)	Au1—N21—H02	106 (3)
C22—N21—Au1	112.8 (2)	N21—C22—H22A	109.7
N21—C22—C23	109.9 (3)	C23—C22—H22A	109.7
C22—C23—C24	112.8 (3)	N21—C22—H22B	109.7
C25—C24—C23	110.5 (3)	C23—C22—H22B	109.7
C25—C24—C27	111.2 (3)	H22A—C22—H22B	108.2
C23—C24—C27	111.4 (3)	C22—C23—H23A	109.0
C26—C25—C24	112.6 (3)	C24—C23—H23A	109.0
N21—C26—C25	110.7 (3)	C22—C23—H23B	109.0
C12—N11—H01	109 (3)	C24—C23—H23B	109.0
C16—N11—H01	109 (3)	H23A—C23—H23B	107.8
Au1—N11—H01	102 (3)	C25—C24—H24	107.9
N11—C12—H12A	109.4	C23—C24—H24	107.9
C13—C12—H12A	109.4	C27—C24—H24	107.9
N11—C12—H12B	109.4	C26—C25—H25A	109.1
C13—C12—H12B	109.4	C24—C25—H25A	109.1
H12A—C12—H12B	108.0	C26—C25—H25B	109.1
C12—C13—H13A	109.1	C24—C25—H25B	109.1
C14—C13—H13A	109.1	H25A—C25—H25B	107.8
C12—C13—H13B	109.1	N21—C26—H26A	109.5
C14—C13—H13B	109.1	C25—C26—H26A	109.5
H13A—C13—H13B	107.9	N21—C26—H26B	109.5
C17—C14—H14	107.8	C25—C26—H26B	109.5
C15—C14—H14	107.8	H26A—C26—H26B	108.1
C13—C14—H14	107.8	C24—C27—H27A	109.5
C16—C15—H15A	109.2	C24—C27—H27B	109.5
C14—C15—H15A	109.2	H27A—C27—H27B	109.5
C16—C15—H15B	109.2	C24—C27—H27C	109.5
C14—C15—H15B	109.2	H27A—C27—H27C	109.5
H15A—C15—H15B	107.9	H27B—C27—H27C	109.5
N11—C16—H16A	109.6
C16—N11—C12—C13	60.1 (4)	C26—N21—C22—C23	61.4 (4)
Au1—N11—C12—C13	−67.1 (3)	Au1—N21—C22—C23	−65.0 (3)
N11—C12—C13—C14	−56.3 (4)	N21—C22—C23—C24	−56.1 (4)
C12—C13—C14—C17	175.6 (3)	C22—C23—C24—C25	49.5 (4)
C12—C13—C14—C15	51.1 (4)	C22—C23—C24—C27	173.6 (3)
C17—C14—C15—C16	−176.5 (3)	C23—C24—C25—C26	−49.2 (4)
C13—C14—C15—C16	−52.0 (4)	C27—C24—C25—C26	−173.4 (3)
C12—N11—C16—C15	−60.6 (4)	C22—N21—C26—C25	−61.6 (4)
Au1—N11—C16—C15	67.2 (3)	Au1—N21—C26—C25	64.9 (3)
C14—C15—C16—N11	57.6 (4)	C24—C25—C26—N21	56.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H02···Cl1	0.92 (3)	2.23 (3)	3.144 (3)	171 (3)
N11—H01···Cl1^i	0.90 (3)	2.25 (3)	3.140 (3)	170 (4)
C16—H16A···Cl1^ii	0.99	2.85	3.623 (4)	136
C22—H22B···Au1^ii	0.99	2.80	3.724 (4)	155
C23—H23A···Au1^iii	0.99	2.85	3.685 (4)	143

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

Bis(4-methylpiperidine-κN)gold(I) dichloridoaurate(I) (2)

Crystal data

[Au(C6H13N)2][AuCl2]	Z = 2
Mr = 663.18	F(000) = 608
Triclinic, P1	Dx = 2.607 Mg m^−3
a = 9.6998 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7001 (8) Å	Cell parameters from 20172 reflections
c = 10.7194 (5) Å	θ = 2.4–30.8°
α = 102.218 (6)°	µ = 17.65 mm^−1
β = 101.893 (5)°	T = 100 K
γ = 114.695 (8)°	Block, colourless
V = 844.89 (11) Å^3	0.15 × 0.03 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	4874 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4690 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.080
ω scan	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −13→13
Tmin = 0.388, Tmax = 1.000	k = −13→13
54252 measured reflections	l = −15→15

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)] = 0.029	Hydrogen site location: mixed
wR(F^2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0107P)^2 + 9.0373P] where P = (Fo^2 + 2Fc^2)/3
4874 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 2.02 e Å^−3
1 restraint	Δρmin = −2.52 e Å^−3

Special details

Geometry. Additional structural data:

Torsion angles: -3.13 ( 0.18) N11 - Au1 - Au2 - Cl1 -177.48 ( 0.18) N11 - Au1 - Au2 - Cl2 176.53 ( 0.19) N21 - Au1 - Au2 - Cl1 2.18 ( 0.19) N21 - Au1 - Au2 - Cl2 0.00 ( 0.00) Au2_$1 - Au1 - Au2 - Au1_$1 0.00 ( 0.00) Au2 - Au1 - Au2_$1 - Au1_$1 0.55 ( 0.66) C12 - N11 - N21 - C22 -0.66 ( 0.65) C16 - N11 - N21 - C26

Non-bonded distance: 5.3963 (0.0006) Au1 - Au1_$1 3.5051 (0.0008) Au2 - Au2_S1

Angles in H2Cl2 ring: 88.83 ( 2.82) H01 - Cl1 - H02_$1 88.51 ( 2.89) H01_$1 - Cl2 - H02 91.43 ( 2.06) Cl1 - H01 - Cl2_$1 91.13 ( 2.23) Cl1_$1 - H02 - Cl2

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

	x	y	z	Uiso*/Ueq
Au1	0.34494 (3)	0.35477 (3)	0.15546 (3)	0.01219 (6)
Au2	0.61479 (3)	0.67852 (3)	0.13899 (3)	0.01717 (7)
Cl1	0.8285 (2)	0.6453 (3)	0.2297 (2)	0.0231 (4)
Cl2	0.4149 (2)	0.7390 (2)	0.0684 (2)	0.0198 (4)
N11	0.5267 (7)	0.3046 (7)	0.2280 (6)	0.0112 (11)
H01	0.606 (9)	0.357 (10)	0.190 (8)	0.01 (2)*
C12	0.4725 (9)	0.1288 (9)	0.1908 (8)	0.0160 (14)
H12A	0.566659	0.111854	0.217324	0.019*
H12B	0.419603	0.076605	0.091666	0.019*
C13	0.3549 (9)	0.0532 (9)	0.2624 (8)	0.0162 (14)
H13A	0.322562	−0.062807	0.239218	0.019*
H13B	0.257095	0.062502	0.229561	0.019*
C14	0.4282 (10)	0.1339 (10)	0.4167 (8)	0.0179 (15)
H14	0.518867	0.112370	0.449831	0.022*
C15	0.4954 (9)	0.3159 (9)	0.4524 (7)	0.0157 (14)
H15A	0.405314	0.339488	0.428818	0.019*
H15B	0.551936	0.368507	0.551193	0.019*
C16	0.6112 (9)	0.3857 (9)	0.3783 (8)	0.0168 (15)
H16A	0.650234	0.503004	0.402217	0.020*
H16B	0.705164	0.368771	0.405836	0.020*
C17	0.3025 (11)	0.0634 (11)	0.4841 (9)	0.0271 (19)
H17A	0.352868	0.111307	0.582603	0.041*
H17B	0.259608	−0.053520	0.457264	0.041*
H17C	0.214780	0.087344	0.455363	0.041*
N21	0.1546 (7)	0.3937 (7)	0.0850 (6)	0.0127 (12)
H02	0.182 (13)	0.453 (12)	0.025 (9)	0.03 (3)*
C22	0.0007 (9)	0.2393 (10)	0.0106 (8)	0.0196 (15)
H22A	0.015903	0.171266	−0.062462	0.023*
H22B	−0.084368	0.262574	−0.031300	0.023*
C23	−0.0507 (9)	0.1495 (10)	0.1071 (9)	0.0209 (16)
H23A	0.030961	0.119174	0.143159	0.025*
H23B	−0.153749	0.049084	0.056799	0.025*
C24	−0.0713 (9)	0.2496 (10)	0.2247 (8)	0.0194 (16)
H24	−0.164643	0.265908	0.187621	0.023*
C25	0.0786 (9)	0.4153 (10)	0.2927 (8)	0.0184 (15)
H25A	0.057033	0.483991	0.359758	0.022*
H25B	0.168456	0.402692	0.341894	0.022*
C26	0.1285 (9)	0.4984 (9)	0.1924 (8)	0.0174 (15)
H26A	0.043789	0.521809	0.149634	0.021*
H26B	0.228953	0.601968	0.240362	0.021*
C27	−0.1075 (11)	0.1642 (12)	0.3275 (10)	0.0276 (19)
H27A	−0.207149	0.061261	0.283271	0.041*
H27B	−0.119850	0.231831	0.401554	0.041*
H27C	−0.018602	0.144513	0.363625	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01125 (12)	0.01256 (13)	0.01533 (12)	0.00698 (9)	0.00522 (9)	0.00603 (10)
Au2	0.01947 (14)	0.01454 (14)	0.01872 (13)	0.00773 (10)	0.00946 (11)	0.00583 (11)
Cl1	0.0200 (9)	0.0265 (10)	0.0237 (9)	0.0100 (8)	0.0095 (7)	0.0102 (8)
Cl2	0.0241 (9)	0.0173 (9)	0.0241 (9)	0.0119 (7)	0.0132 (8)	0.0091 (7)
N11	0.008 (2)	0.012 (3)	0.011 (3)	0.004 (2)	0.000 (2)	0.001 (2)
C12	0.017 (3)	0.014 (3)	0.020 (4)	0.010 (3)	0.008 (3)	0.005 (3)
C13	0.014 (3)	0.014 (3)	0.020 (4)	0.007 (3)	0.005 (3)	0.005 (3)
C14	0.023 (4)	0.020 (4)	0.018 (4)	0.014 (3)	0.010 (3)	0.010 (3)
C15	0.020 (3)	0.018 (4)	0.014 (3)	0.013 (3)	0.007 (3)	0.007 (3)
C16	0.013 (3)	0.015 (3)	0.020 (4)	0.007 (3)	0.005 (3)	0.004 (3)
C17	0.034 (5)	0.027 (4)	0.028 (4)	0.015 (4)	0.018 (4)	0.016 (4)
N21	0.012 (3)	0.010 (3)	0.012 (3)	0.004 (2)	0.002 (2)	0.003 (2)
C22	0.016 (3)	0.022 (4)	0.016 (3)	0.010 (3)	0.001 (3)	0.001 (3)
C23	0.010 (3)	0.022 (4)	0.029 (4)	0.006 (3)	0.003 (3)	0.013 (3)
C24	0.014 (3)	0.024 (4)	0.028 (4)	0.012 (3)	0.008 (3)	0.014 (3)
C25	0.018 (3)	0.024 (4)	0.019 (4)	0.013 (3)	0.008 (3)	0.010 (3)
C26	0.016 (3)	0.018 (4)	0.022 (4)	0.009 (3)	0.008 (3)	0.008 (3)
C27	0.022 (4)	0.035 (5)	0.037 (5)	0.015 (4)	0.018 (4)	0.023 (4)

Geometric parameters (Å, º)

Au1—N21	2.062 (7)	C13—H13A	0.9900
Au1—N11	2.064 (6)	C13—H13B	0.9900
Au1—Au2	3.2096 (5)	C14—H14	1.0000
Au1—Au2^i	3.2252 (4)	C15—H15A	0.9900
Au2—Cl1	2.282 (2)	C15—H15B	0.9900
Au2—Cl2	2.282 (2)	C16—H16A	0.9900
N11—C12	1.490 (9)	C16—H16B	0.9900
N11—C16	1.506 (9)	C17—H17A	0.9800
C12—C13	1.525 (10)	C17—H17B	0.9800
C13—C14	1.535 (11)	C17—H17C	0.9800
C14—C15	1.529 (10)	N21—H02	0.95 (6)
C14—C17	1.533 (11)	C22—H22A	0.9900
C15—C16	1.520 (10)	C22—H22B	0.9900
N21—C22	1.498 (9)	C23—H23A	0.9900
N21—C26	1.504 (10)	C23—H23B	0.9900
C22—C23	1.520 (11)	C24—H24	1.0000
C23—C24	1.523 (12)	C25—H25A	0.9900
C24—C27	1.525 (11)	C25—H25B	0.9900
C24—C25	1.531 (11)	C26—H26A	0.9900
C25—C26	1.516 (11)	C26—H26B	0.9900
N11—H01	0.95 (6)	C27—H27A	0.9800
C12—H12A	0.9900	C27—H27B	0.9800
C12—H12B	0.9900	C27—H27C	0.9800
N21—Au1—N11	176.8 (2)	C17—C14—H14	108.5
N21—Au1—Au2	95.61 (17)	C13—C14—H14	108.5
N11—Au1—Au2	87.59 (17)	C16—C15—H15A	109.2
N21—Au1—Au2^i	87.50 (18)	C14—C15—H15A	109.2
N11—Au1—Au2^i	94.13 (17)	C16—C15—H15B	109.2
Au2—Au1—Au2^i	66.011 (12)	C14—C15—H15B	109.2
Cl1—Au2—Cl2	173.42 (7)	H15A—C15—H15B	107.9
Cl1—Au2—Au1	96.01 (5)	N11—C16—H16A	109.8
Cl2—Au2—Au1	87.38 (5)	C15—C16—H16A	109.8
Cl1—Au2—Au1^i	95.47 (5)	N11—C16—H16B	109.8
Cl2—Au2—Au1^i	88.25 (5)	C15—C16—H16B	109.8
Au1—Au2—Au1^i	113.989 (13)	H16A—C16—H16B	108.2
Cl1—Au2—Au2^i	100.58 (6)	C14—C17—H17A	109.5
Cl2—Au2—Au2^i	85.99 (5)	C14—C17—H17B	109.5
Au1—Au2—Au2^i	57.208 (12)	H17A—C17—H17B	109.5
Au1^i—Au2—Au2^i	56.781 (11)	C14—C17—H17C	109.5
C12—N11—C16	110.0 (6)	H17A—C17—H17C	109.5
C12—N11—Au1	113.2 (4)	H17B—C17—H17C	109.5
C16—N11—Au1	113.2 (5)	C22—N21—H02	110 (7)
N11—C12—C13	110.0 (6)	C26—N21—H02	105 (7)
C12—C13—C14	112.1 (6)	Au1—N21—H02	106 (7)
C15—C14—C17	111.4 (7)	N21—C22—H22A	109.6
C15—C14—C13	109.5 (6)	C23—C22—H22A	109.6
C17—C14—C13	110.5 (7)	N21—C22—H22B	109.6
C16—C15—C14	112.0 (6)	C23—C22—H22B	109.6
N11—C16—C15	109.5 (6)	H22A—C22—H22B	108.1
C22—N21—C26	109.1 (6)	C22—C23—H23A	109.1
C22—N21—Au1	112.1 (5)	C24—C23—H23A	109.1
C26—N21—Au1	114.3 (5)	C22—C23—H23B	109.1
N21—C22—C23	110.2 (6)	C24—C23—H23B	109.1
C22—C23—C24	112.3 (7)	H23A—C23—H23B	107.9
C23—C24—C27	111.7 (7)	C23—C24—H24	108.0
C23—C24—C25	110.2 (6)	C27—C24—H24	108.0
C27—C24—C25	110.7 (7)	C25—C24—H24	108.0
C26—C25—C24	112.6 (7)	C26—C25—H25A	109.1
N21—C26—C25	110.5 (6)	C24—C25—H25A	109.1
C12—N11—H01	112 (5)	C26—C25—H25B	109.1
C16—N11—H01	104 (5)	C24—C25—H25B	109.1
Au1—N11—H01	104 (5)	H25A—C25—H25B	107.8
N11—C12—H12A	109.7	N21—C26—H26A	109.6
C13—C12—H12A	109.7	C25—C26—H26A	109.6
N11—C12—H12B	109.7	N21—C26—H26B	109.6
C13—C12—H12B	109.7	C25—C26—H26B	109.6
H12A—C12—H12B	108.2	H26A—C26—H26B	108.1
C12—C13—H13A	109.2	C24—C27—H27A	109.5
C14—C13—H13A	109.2	C24—C27—H27B	109.5
C12—C13—H13B	109.2	H27A—C27—H27B	109.5
C14—C13—H13B	109.2	C24—C27—H27C	109.5
H13A—C13—H13B	107.9	H27A—C27—H27C	109.5
C15—C14—H14	108.5	H27B—C27—H27C	109.5
C16—N11—C12—C13	60.8 (8)	C26—N21—C22—C23	−61.3 (8)
Au1—N11—C12—C13	−66.9 (7)	Au1—N21—C22—C23	66.3 (7)
N11—C12—C13—C14	−57.1 (8)	N21—C22—C23—C24	57.5 (8)
C12—C13—C14—C15	52.6 (8)	C22—C23—C24—C27	−174.6 (7)
C12—C13—C14—C17	175.7 (7)	C22—C23—C24—C25	−51.2 (9)
C17—C14—C15—C16	−175.9 (7)	C23—C24—C25—C26	50.6 (9)
C13—C14—C15—C16	−53.4 (8)	C27—C24—C25—C26	174.6 (7)
C12—N11—C16—C15	−61.3 (8)	C22—N21—C26—C25	60.7 (8)
Au1—N11—C16—C15	66.4 (7)	Au1—N21—C26—C25	−65.7 (7)
C14—C15—C16—N11	58.1 (8)	C24—C25—C26—N21	−56.1 (9)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Cl1	0.95 (6)	2.59 (7)	3.370 (6)	139 (7)
N11—H01···Cl2^i	0.95 (6)	2.66 (8)	3.312 (7)	126 (6)
N21—H02···Cl2	0.95 (6)	2.61 (9)	3.316 (7)	131 (8)
N21—H02···Cl1^i	0.95 (6)	2.66 (9)	3.360 (7)	130 (8)
C13—H13A···Cl2^ii	0.99	2.91	3.640 (8)	131

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

Bis(4-methylpiperidine-κN)gold(I) dibromidoaurate(I) (3)

Crystal data

[Au(C6H13N)2][AuBr2]	Z = 2
Mr = 752.10	F(000) = 680
Triclinic, P1	Dx = 2.876 Mg m^−3
a = 9.8461 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7728 (4) Å	Cell parameters from 12875 reflections
c = 10.9461 (5) Å	θ = 2.6–30.3°
α = 100.136 (4)°	µ = 21.46 mm^−1
β = 103.685 (5)°	T = 100 K
γ = 116.287 (5)°	Block, colourless
V = 868.59 (9) Å^3	0.08 × 0.06 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	5188 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4466 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.050
ω scan	θmax = 31.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −14→14
Tmin = 0.576, Tmax = 1.000	k = −14→13
48187 measured reflections	l = −15→15

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)] = 0.023	Hydrogen site location: mixed
wR(F^2) = 0.041	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0127P)^2 + 1.3346P] where P = (Fo^2 + 2Fc^2)/3
5188 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 1.02 e Å^−3
1 restraint	Δρmin = −1.15 e Å^−3

Special details

Geometry. Additional structural data:

Non-bonded distance: 5.5563 (0.0004) Au1 - Au1_$1

Torsion angles: -3.06 ( 0.09) N11 - Au1 - Au2 - Br1 -175.21 ( 0.09) N11 - Au1 - Au2 - Br2 175.95 ( 0.08) N21 - Au1 - Au2 - Br1 3.79 ( 0.08) N21 - Au1 - Au2 - Br2 0.00 ( 0.00) Au2_$1 - Au1 - Au2 - Au1_$1 0.00 ( 0.00) Au2 - Au1 - Au2_$1 - Au1_$1 2.08 ( 0.31) C12 - N11 - N21 - C22 0.99 ( 0.32) C16 - N11 - N21 - C26

Operators for generating equivalent atoms: $1 -x+1, -y+1, -z

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

	x	y	z	Uiso*/Ueq
Au1	0.34246 (2)	0.35042 (2)	0.15864 (2)	0.01326 (4)
Au2	0.62704 (2)	0.68148 (2)	0.13846 (2)	0.01800 (4)
Br1	0.85675 (5)	0.65879 (5)	0.24231 (4)	0.02139 (8)
Br2	0.42027 (5)	0.74623 (5)	0.06245 (4)	0.01870 (8)
N11	0.5261 (4)	0.3083 (4)	0.2396 (3)	0.0146 (6)
H01	0.597 (5)	0.352 (5)	0.199 (4)	0.031 (13)*
C12	0.4724 (5)	0.1335 (4)	0.2092 (4)	0.0174 (8)
H12A	0.568195	0.120983	0.238943	0.021*
H12B	0.418198	0.078799	0.112095	0.021*
C13	0.3569 (5)	0.0555 (4)	0.2781 (4)	0.0172 (8)
H13A	0.326771	−0.059071	0.259395	0.021*
H13B	0.256719	0.058865	0.241634	0.021*
C14	0.4302 (5)	0.1390 (5)	0.4283 (4)	0.0187 (8)
H14	0.522920	0.122592	0.465036	0.022*
C15	0.4963 (5)	0.3198 (4)	0.4574 (4)	0.0170 (8)
H15A	0.404566	0.338866	0.430613	0.020*
H15B	0.554663	0.375071	0.554164	0.020*
C16	0.6104 (4)	0.3918 (4)	0.3849 (3)	0.0158 (7)
H16A	0.647748	0.508115	0.404629	0.019*
H16B	0.706631	0.380388	0.416039	0.019*
C17	0.3069 (5)	0.0671 (5)	0.4946 (4)	0.0272 (9)
H17A	0.359292	0.118548	0.591142	0.041*
H17B	0.265399	−0.049068	0.472803	0.041*
H17C	0.216830	0.085712	0.462499	0.041*
N21	0.1493 (4)	0.3816 (4)	0.0822 (3)	0.0151 (6)
H02	0.171 (6)	0.430 (5)	0.021 (4)	0.033 (13)*
C22	−0.0056 (5)	0.2246 (5)	0.0142 (4)	0.0194 (8)
H22A	0.007975	0.154374	−0.053028	0.023*
H22B	−0.091892	0.243355	−0.032194	0.023*
C23	−0.0549 (5)	0.1417 (5)	0.1134 (4)	0.0226 (8)
H23A	0.027452	0.115019	0.153904	0.027*
H23B	−0.159362	0.039296	0.066307	0.027*
C24	−0.0728 (5)	0.2453 (5)	0.2231 (4)	0.0207 (8)
H24	−0.166501	0.258762	0.182547	0.025*
C25	0.0802 (5)	0.4118 (5)	0.2853 (4)	0.0184 (8)
H25A	0.061751	0.482870	0.347349	0.022*
H25B	0.170552	0.401935	0.337243	0.022*
C26	0.1279 (5)	0.4885 (5)	0.1823 (4)	0.0180 (8)
H26A	0.042993	0.509416	0.136656	0.022*
H26B	0.230477	0.593130	0.226770	0.022*
C27	−0.1067 (5)	0.1650 (6)	0.3281 (5)	0.0303 (10)
H27A	−0.205630	0.058909	0.286356	0.045*
H27B	−0.121036	0.232218	0.395758	0.045*
H27C	−0.015303	0.152108	0.369797	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01451 (7)	0.01374 (7)	0.01331 (7)	0.00839 (6)	0.00551 (5)	0.00415 (5)
Au2	0.02091 (8)	0.01803 (8)	0.01796 (8)	0.01101 (7)	0.00943 (6)	0.00563 (6)
Br1	0.01983 (19)	0.0256 (2)	0.01905 (19)	0.01164 (17)	0.00751 (16)	0.00668 (16)
Br2	0.0237 (2)	0.01820 (19)	0.01945 (18)	0.01302 (17)	0.01113 (16)	0.00622 (15)
N11	0.0174 (16)	0.0147 (16)	0.0156 (15)	0.0109 (14)	0.0062 (13)	0.0056 (13)
C12	0.0201 (19)	0.017 (2)	0.0172 (18)	0.0114 (17)	0.0070 (16)	0.0030 (15)
C13	0.0181 (19)	0.0107 (18)	0.0208 (19)	0.0073 (16)	0.0052 (16)	0.0029 (15)
C14	0.0190 (19)	0.021 (2)	0.0200 (19)	0.0128 (17)	0.0076 (16)	0.0083 (16)
C15	0.0174 (19)	0.018 (2)	0.0134 (17)	0.0084 (16)	0.0043 (15)	0.0044 (15)
C16	0.0159 (18)	0.0138 (19)	0.0117 (17)	0.0056 (16)	0.0016 (14)	0.0010 (14)
C17	0.033 (2)	0.029 (2)	0.022 (2)	0.014 (2)	0.0141 (19)	0.0124 (19)
N21	0.0174 (16)	0.0162 (17)	0.0123 (15)	0.0092 (14)	0.0055 (13)	0.0038 (13)
C22	0.0160 (19)	0.024 (2)	0.0132 (18)	0.0102 (17)	0.0010 (15)	0.0012 (15)
C23	0.017 (2)	0.018 (2)	0.026 (2)	0.0055 (17)	0.0049 (17)	0.0050 (17)
C24	0.0137 (19)	0.023 (2)	0.025 (2)	0.0086 (17)	0.0069 (16)	0.0090 (17)
C25	0.019 (2)	0.021 (2)	0.0171 (18)	0.0115 (17)	0.0081 (16)	0.0043 (16)
C26	0.020 (2)	0.019 (2)	0.0216 (19)	0.0137 (17)	0.0107 (16)	0.0084 (16)
C27	0.025 (2)	0.038 (3)	0.034 (3)	0.015 (2)	0.015 (2)	0.021 (2)

Geometric parameters (Å, º)

Au1—N11	2.062 (3)	C13—H13A	0.9900
Au1—N21	2.064 (3)	C13—H13B	0.9900
Au1—Au2	3.2988 (3)	C14—H14	1.0000
Au1—Au2^i	3.3094 (2)	C15—H15A	0.9900
Au2—Br2	2.4006 (4)	C15—H15B	0.9900
Au2—Br1	2.4027 (4)	C16—H16A	0.9900
N11—C16	1.485 (5)	C16—H16B	0.9900
N11—C12	1.492 (5)	C17—H17A	0.9800
C12—C13	1.511 (5)	C17—H17B	0.9800
C13—C14	1.527 (5)	C17—H17C	0.9800
C14—C15	1.527 (5)	N21—H02	0.89 (3)
C14—C17	1.529 (5)	C22—H22A	0.9900
C15—C16	1.518 (5)	C22—H22B	0.9900
N21—C22	1.491 (5)	C23—H23A	0.9900
N21—C26	1.496 (5)	C23—H23B	0.9900
C22—C23	1.511 (5)	C24—H24	1.0000
C23—C24	1.526 (6)	C25—H25A	0.9900
C24—C27	1.521 (5)	C25—H25B	0.9900
C24—C25	1.528 (5)	C26—H26A	0.9900
C25—C26	1.513 (5)	C26—H26B	0.9900
N11—H01	0.90 (3)	C27—H27A	0.9800
C12—H12A	0.9900	C27—H27B	0.9800
C12—H12B	0.9900	C27—H27C	0.9800
N11—Au1—N21	176.30 (13)	C16—C15—H15A	109.1
N11—Au1—Au2	86.25 (9)	C14—C15—H15A	109.1
N21—Au1—Au2	97.32 (9)	C16—C15—H15B	109.1
N11—Au1—Au2^i	96.43 (9)	C14—C15—H15B	109.1
N21—Au1—Au2^i	85.98 (8)	H15A—C15—H15B	107.8
Au2—Au1—Au2^i	65.548 (9)	N11—C16—H16A	109.7
Br2—Au2—Br1	170.628 (15)	C15—C16—H16A	109.7
Br2—Au2—Au1	87.120 (12)	N11—C16—H16B	109.7
Br1—Au2—Au1	98.067 (12)	C15—C16—H16B	109.7
Br2—Au2—Au1^i	87.536 (11)	H16A—C16—H16B	108.2
Br1—Au2—Au1^i	97.312 (11)	C14—C17—H17A	109.5
Au1—Au2—Au1^i	114.452 (8)	C14—C17—H17B	109.5
C16—N11—C12	109.8 (3)	H17A—C17—H17B	109.5
C16—N11—Au1	113.2 (2)	C14—C17—H17C	109.5
C12—N11—Au1	113.4 (2)	H17A—C17—H17C	109.5
N11—C12—C13	110.8 (3)	H17B—C17—H17C	109.5
C12—C13—C14	112.3 (3)	C22—N21—H02	108 (3)
C15—C14—C13	109.3 (3)	C26—N21—H02	107 (3)
C15—C14—C17	111.5 (3)	Au1—N21—H02	106 (3)
C13—C14—C17	111.5 (3)	N21—C22—H22A	109.5
C16—C15—C14	112.4 (3)	C23—C22—H22A	109.5
N11—C16—C15	110.0 (3)	N21—C22—H22B	109.5
C22—N21—C26	109.5 (3)	C23—C22—H22B	109.5
C22—N21—Au1	111.9 (2)	H22A—C22—H22B	108.1
C26—N21—Au1	114.0 (2)	C22—C23—H23A	109.1
N21—C22—C23	110.6 (3)	C24—C23—H23A	109.1
C22—C23—C24	112.6 (3)	C22—C23—H23B	109.1
C27—C24—C23	111.1 (3)	C24—C23—H23B	109.1
C27—C24—C25	110.8 (3)	H23A—C23—H23B	107.8
C23—C24—C25	109.7 (3)	C27—C24—H24	108.4
C26—C25—C24	112.4 (3)	C23—C24—H24	108.4
N21—C26—C25	111.1 (3)	C25—C24—H24	108.4
C16—N11—H01	108 (3)	C26—C25—H25A	109.1
C12—N11—H01	109 (3)	C24—C25—H25A	109.1
Au1—N11—H01	103 (3)	C26—C25—H25B	109.1
N11—C12—H12A	109.5	C24—C25—H25B	109.1
C13—C12—H12A	109.5	H25A—C25—H25B	107.9
N11—C12—H12B	109.5	N21—C26—H26A	109.4
C13—C12—H12B	109.5	C25—C26—H26A	109.4
H12A—C12—H12B	108.1	N21—C26—H26B	109.4
C12—C13—H13A	109.1	C25—C26—H26B	109.4
C14—C13—H13A	109.1	H26A—C26—H26B	108.0
C12—C13—H13B	109.1	C24—C27—H27A	109.5
C14—C13—H13B	109.1	C24—C27—H27B	109.5
H13A—C13—H13B	107.9	H27A—C27—H27B	109.5
C15—C14—H14	108.2	C24—C27—H27C	109.5
C13—C14—H14	108.2	H27A—C27—H27C	109.5
C17—C14—H14	108.2	H27B—C27—H27C	109.5
C16—N11—C12—C13	60.2 (4)	C26—N21—C22—C23	−60.0 (4)
Au1—N11—C12—C13	−67.5 (3)	Au1—N21—C22—C23	67.3 (3)
N11—C12—C13—C14	−56.5 (4)	N21—C22—C23—C24	57.3 (4)
C12—C13—C14—C15	51.7 (4)	C22—C23—C24—C27	−174.6 (3)
C12—C13—C14—C17	175.4 (3)	C22—C23—C24—C25	−51.7 (4)
C13—C14—C15—C16	−52.4 (4)	C27—C24—C25—C26	174.0 (3)
C17—C14—C15—C16	−176.1 (3)	C23—C24—C25—C26	51.0 (4)
C12—N11—C16—C15	−60.4 (4)	C22—N21—C26—C25	59.7 (4)
Au1—N11—C16—C15	67.4 (3)	Au1—N21—C26—C25	−66.5 (3)
C14—C15—C16—N11	57.7 (4)	C24—C25—C26—N21	−56.1 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Br2^i	0.90 (3)	2.80 (4)	3.457 (3)	131 (4)
N11—H01···Br1	0.90 (3)	2.81 (4)	3.518 (3)	136 (4)
N21—H02···Br1^i	0.89 (3)	2.77 (4)	3.487 (3)	138 (4)
N21—H02···Br2	0.89 (3)	2.84 (4)	3.462 (3)	128 (4)
C13—H13A···Br2^ii	0.99	3.19	3.867 (4)	127

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

Chlorido(4-methylpiperidine-κN)gold(I) bis(4-methylpiperidine-κN)gold(I) chloride dichloromethane monosolvate (4)

Crystal data

[Au(C6H13N)2]Cl·[AuCl(C6H13N)]·CH2Cl2	F(000) = 3216
Mr = 847.28	Dx = 2.079 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.5785 (7) Å	Cell parameters from 14529 reflections
b = 16.0876 (4) Å	θ = 2.4–26.3°
c = 18.2247 (7) Å	µ = 11.23 mm^−1
β = 116.196 (5)°	T = 101 K
V = 5413.7 (4) Å^3	Block, colourless
Z = 8	0.25 × 0.1 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	13423 independent reflections
Radiation source: Enhance (Mo) X-ray Source	11445 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.122
ω scan	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −27→27
Tmin = 0.580, Tmax = 1.000	k = −21→21
134776 measured reflections	l = −24→24

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)] = 0.040	Hydrogen site location: mixed
wR(F^2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0102P)^2 + 6.0221P] where P = (Fo^2 + 2Fc^2)/3
13423 reflections	(Δ/σ)max = 0.001
530 parameters	Δρmax = 2.02 e Å^−3
15 restraints	Δρmin = −1.91 e Å^−3

Special details

Geometry. Additional structural data:

Torsion angles:

85.28 ( 0.32) N11 - Au1 - Au2 - N31 -93.19 ( 0.24) N11 - Au1 - Au2 - Cl1 -93.64 ( 0.31) N21 - Au1 - Au2 - N31 87.89 ( 0.24) N21 - Au1 - Au2 - Cl1 -84.62 ( 0.33) N41 - Au3 - Au4 - N61 95.00 ( 0.24) N41 - Au3 - Au4 - Cl2 93.92 ( 0.33) N51 - Au3 - Au4 - N61 -86.46 ( 0.25) N51 - Au3 - Au4 - Cl2 5.18 ( 0.90) C12 - N11 - N21 - C22 -119.25 ( 0.81) C16 - N11 - N21 - C22 132.02 ( 0.84) C12 - N11 - N21 - C26 132.02 ( 0.84) C12 - N11 - N21 - C26 -4.21 ( 0.93) C42 - N41 - N51 - C52 120.72 ( 0.84) C46 - N41 - N51 - C52 -129.55 ( 0.85) C42 - N41 - N51 - C56 -129.55 ( 0.85) C42 - N41 - N51 - C56

Angles H···Cl···H:

82.86 ( 3.36) H11 - Cl3 - H31 80.32 ( 3.36) H41 - Cl4 - H61

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

	x	y	z	Uiso*/Ueq
Au1	−0.00202 (2)	0.49114 (2)	0.16824 (2)	0.01553 (10)
Au2	0.02294 (2)	0.29093 (2)	0.14623 (2)	0.01759 (10)
Au3	0.49092 (2)	0.48860 (2)	0.32562 (2)	0.01468 (9)
Au4	0.51565 (2)	0.29110 (2)	0.36978 (2)	0.01682 (10)
Cl1	0.04557 (13)	0.26028 (15)	0.27672 (17)	0.0199 (6)
Cl2	0.54217 (14)	0.25973 (15)	0.26510 (18)	0.0210 (6)
Cl3	−0.14385 (12)	0.43026 (14)	−0.06278 (14)	0.0176 (5)
Cl4	0.35323 (12)	0.43684 (14)	0.42016 (14)	0.0171 (5)
N11	−0.1105 (4)	0.4626 (6)	0.1235 (5)	0.022 (2)
H11	−0.120 (5)	0.454 (7)	0.076 (3)	0.026*
C12	−0.1544 (6)	0.5345 (7)	0.1302 (7)	0.027 (3)
H12A	−0.206637	0.520966	0.101332	0.033*
H12B	−0.145464	0.584359	0.104040	0.033*
C13	−0.1337 (5)	0.5525 (6)	0.2192 (7)	0.022 (2)
H13A	−0.164700	0.597953	0.222449	0.027*
H13B	−0.082917	0.572198	0.245668	0.027*
C14	−0.1409 (6)	0.4778 (6)	0.2667 (6)	0.021 (2)
H14	−0.193596	0.464758	0.245235	0.025*
C15	−0.1037 (5)	0.4015 (6)	0.2513 (6)	0.019 (2)
H15A	−0.050539	0.408929	0.280040	0.023*
H15B	−0.116234	0.351498	0.274063	0.023*
C16	−0.1262 (5)	0.3883 (6)	0.1614 (7)	0.021 (2)
H16A	−0.099997	0.339687	0.154181	0.025*
H16B	−0.178699	0.376047	0.133246	0.025*
C17	−0.1125 (6)	0.4981 (7)	0.3567 (7)	0.035 (3)
H17A	−0.060280	0.508489	0.380120	0.052*
H17B	−0.121780	0.451130	0.385027	0.052*
H17C	−0.137105	0.547699	0.363137	0.052*
N21	0.1035 (4)	0.5275 (5)	0.2110 (5)	0.0165 (17)
H21	0.115 (5)	0.526 (6)	0.174 (4)	0.020*
C22	0.1166 (6)	0.6129 (6)	0.2472 (6)	0.023 (3)
H22A	0.081939	0.652411	0.207607	0.027*
H22B	0.166235	0.631089	0.259354	0.027*
C23	0.1073 (6)	0.6127 (6)	0.3247 (7)	0.023 (2)
H23A	0.055927	0.601273	0.310880	0.028*
H23B	0.119230	0.668603	0.349868	0.028*
C24	0.1545 (5)	0.5488 (6)	0.3866 (7)	0.020 (2)
H24	0.206050	0.567176	0.407701	0.024*
C25	0.1476 (5)	0.4645 (6)	0.3464 (6)	0.017 (2)
H25A	0.184207	0.426436	0.385755	0.021*
H25B	0.099169	0.441272	0.333286	0.021*
C26	0.1574 (5)	0.4675 (6)	0.2695 (7)	0.019 (2)
H26A	0.149851	0.411470	0.244571	0.022*
H26B	0.207262	0.485668	0.282373	0.022*
C27	0.1364 (5)	0.5440 (7)	0.4586 (6)	0.027 (2)
H27A	0.086038	0.525884	0.439523	0.041*
H27B	0.142650	0.598881	0.484136	0.041*
H27C	0.168704	0.504023	0.498717	0.041*
N31	−0.0004 (4)	0.3160 (5)	0.0252 (5)	0.0177 (19)
H31	−0.044 (2)	0.322 (6)	0.001 (5)	0.021*
C32	−0.0067 (5)	0.2378 (6)	−0.0234 (7)	0.020 (2)
H32A	−0.023819	0.251855	−0.081915	0.024*
H32B	−0.042413	0.199609	−0.018603	0.024*
C33	0.0673 (5)	0.1952 (6)	0.0091 (6)	0.023 (2)
H33A	0.081313	0.176391	0.065813	0.027*
H33B	0.063100	0.145339	−0.024515	0.027*
C34	0.1270 (6)	0.2507 (6)	0.0086 (8)	0.020 (3)
H34	0.115419	0.263182	−0.049648	0.024*
C35	0.1277 (5)	0.3334 (6)	0.0513 (6)	0.022 (2)
H35A	0.145567	0.323307	0.110620	0.026*
H35B	0.161797	0.372206	0.044044	0.026*
C36	0.0532 (5)	0.3737 (6)	0.0181 (6)	0.023 (2)
H36A	0.056125	0.425300	0.048931	0.027*
H36B	0.037044	0.388730	−0.040052	0.027*
C37	0.2005 (6)	0.2085 (7)	0.0476 (7)	0.032 (3)
H37A	0.209469	0.187211	0.101577	0.048*
H37B	0.238254	0.248766	0.053413	0.048*
H37C	0.201261	0.162363	0.012866	0.048*
N41	0.3823 (4)	0.4645 (6)	0.2614 (5)	0.0184 (19)
H41	0.370 (5)	0.457 (7)	0.298 (4)	0.022*
C42	0.3432 (6)	0.5369 (7)	0.2122 (7)	0.027 (3)
H42A	0.354037	0.586613	0.247699	0.032*
H42B	0.290341	0.526656	0.188180	0.032*
C43	0.3652 (6)	0.5527 (6)	0.1447 (6)	0.025 (3)
H43A	0.416765	0.569628	0.169228	0.030*
H43B	0.336110	0.599171	0.110332	0.030*
C44	0.3551 (5)	0.4764 (6)	0.0906 (6)	0.020 (2)
H44	0.301876	0.466137	0.059446	0.024*
C45	0.3880 (6)	0.4011 (6)	0.1415 (7)	0.022 (2)
H45A	0.441445	0.405876	0.166272	0.026*
H45B	0.373881	0.351296	0.105944	0.026*
C46	0.3642 (6)	0.3904 (7)	0.2087 (7)	0.030 (3)
H46A	0.311222	0.380915	0.184035	0.036*
H46B	0.388377	0.341123	0.242155	0.036*
C47	0.3849 (6)	0.4921 (7)	0.0284 (6)	0.032 (3)
H47A	0.436949	0.503463	0.057320	0.048*
H47B	0.360123	0.540071	−0.005628	0.048*
H47C	0.376662	0.442945	−0.006287	0.048*
N51	0.5979 (5)	0.5227 (5)	0.3903 (5)	0.0198 (19)
H51	0.607 (5)	0.524 (6)	0.438 (3)	0.024*
C52	0.6127 (6)	0.6070 (6)	0.3682 (7)	0.025 (3)
H52A	0.662321	0.624190	0.406880	0.030*
H52B	0.578269	0.647171	0.372847	0.030*
C53	0.6055 (5)	0.6089 (6)	0.2811 (7)	0.023 (3)
H53A	0.554437	0.598064	0.242136	0.028*
H53B	0.618337	0.665074	0.269491	0.028*
C54	0.6537 (5)	0.5451 (6)	0.2678 (7)	0.022 (2)
H54	0.705285	0.562158	0.300923	0.026*
C55	0.6428 (5)	0.4593 (6)	0.2985 (6)	0.018 (2)
H55A	0.594170	0.437916	0.261311	0.022*
H55B	0.679171	0.419995	0.296918	0.022*
C56	0.6497 (5)	0.4630 (7)	0.3839 (7)	0.024 (3)
H56A	0.640831	0.407025	0.400193	0.029*
H56B	0.699679	0.479645	0.421893	0.029*
C57	0.6394 (6)	0.5406 (7)	0.1787 (6)	0.031 (3)
H57A	0.589309	0.523066	0.145183	0.046*
H57B	0.672562	0.500343	0.172767	0.046*
H57C	0.647231	0.595475	0.160586	0.046*
N61	0.4912 (4)	0.3156 (5)	0.4659 (6)	0.022 (2)
H61	0.449 (2)	0.330 (6)	0.445 (6)	0.026*
C62	0.4842 (6)	0.2387 (6)	0.5079 (8)	0.027 (3)
H62A	0.448181	0.200933	0.467391	0.033*
H62B	0.466938	0.253585	0.548994	0.033*
C63	0.5584 (6)	0.1942 (6)	0.5504 (7)	0.029 (3)
H63A	0.553716	0.144733	0.580026	0.035*
H63B	0.573431	0.175051	0.508530	0.035*
C64	0.6159 (6)	0.2519 (6)	0.6101 (8)	0.026 (3)
H64	0.604230	0.263581	0.656895	0.031*
C65	0.6170 (5)	0.3349 (6)	0.5682 (6)	0.019 (2)
H65A	0.650288	0.374174	0.609564	0.023*
H65B	0.635429	0.325182	0.527126	0.023*
C66	0.5420 (5)	0.3729 (5)	0.5268 (6)	0.017 (2)
H66A	0.524759	0.385862	0.568291	0.020*
H66B	0.544164	0.425494	0.499714	0.020*
C67	0.6890 (6)	0.2084 (7)	0.6427 (7)	0.036 (3)
H67A	0.688606	0.159580	0.674544	0.054*
H67B	0.727128	0.246804	0.677648	0.054*
H67C	0.698462	0.190978	0.596735	0.054*
C1	0.2418 (5)	0.2663 (7)	0.3577 (7)	0.026 (3)
H1A	0.261404	0.321997	0.379147	0.031*
H1B	0.189596	0.266190	0.343926	0.031*
Cl5	0.25277 (16)	0.24644 (16)	0.2668 (2)	0.0367 (8)
Cl6	0.28565 (14)	0.19267 (16)	0.43223 (16)	0.0308 (6)
C2	0.7414 (6)	0.2375 (6)	0.3816 (8)	0.024 (3)
H2A	0.690937	0.247144	0.340229	0.029*
H2B	0.753370	0.178499	0.377869	0.029*
Cl7	0.74773 (16)	0.25645 (18)	0.4784 (2)	0.0346 (8)
Cl8	0.80057 (14)	0.30207 (16)	0.35950 (16)	0.0285 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01286 (18)	0.0209 (2)	0.0121 (2)	0.00020 (14)	0.00482 (15)	0.00123 (15)
Au2	0.01393 (18)	0.0174 (2)	0.0192 (2)	0.00127 (14)	0.00528 (16)	0.00212 (16)
Au3	0.01280 (17)	0.0194 (2)	0.0115 (2)	0.00030 (14)	0.00511 (15)	0.00025 (15)
Au4	0.01545 (19)	0.0153 (2)	0.0196 (2)	0.00096 (14)	0.00757 (15)	−0.00137 (15)
Cl1	0.0172 (12)	0.0207 (12)	0.0178 (15)	−0.0011 (9)	0.0040 (11)	0.0016 (10)
Cl2	0.0221 (13)	0.0219 (13)	0.0203 (15)	0.0032 (9)	0.0105 (12)	−0.0024 (10)
Cl3	0.0168 (12)	0.0178 (11)	0.0171 (12)	−0.0010 (9)	0.0066 (10)	0.0009 (10)
Cl4	0.0145 (12)	0.0192 (12)	0.0173 (12)	−0.0008 (9)	0.0068 (10)	−0.0017 (9)
N11	0.013 (4)	0.039 (5)	0.010 (4)	0.000 (4)	0.001 (4)	−0.004 (4)
C12	0.014 (5)	0.039 (7)	0.023 (6)	0.008 (4)	0.002 (5)	0.009 (5)
C13	0.012 (5)	0.021 (6)	0.031 (7)	0.002 (4)	0.007 (5)	−0.001 (5)
C14	0.024 (5)	0.027 (6)	0.012 (5)	−0.008 (4)	0.007 (5)	−0.004 (4)
C15	0.021 (5)	0.018 (5)	0.019 (6)	−0.005 (4)	0.010 (5)	−0.004 (4)
C16	0.015 (5)	0.014 (5)	0.037 (7)	−0.008 (4)	0.014 (5)	−0.012 (5)
C17	0.046 (7)	0.030 (6)	0.028 (7)	−0.005 (5)	0.017 (6)	0.003 (5)
N21	0.011 (4)	0.031 (5)	0.009 (4)	0.001 (3)	0.007 (3)	0.001 (4)
C22	0.026 (6)	0.020 (6)	0.012 (6)	−0.006 (4)	−0.002 (5)	−0.001 (4)
C23	0.027 (6)	0.013 (5)	0.027 (6)	0.004 (4)	0.009 (5)	−0.006 (4)
C24	0.013 (5)	0.024 (6)	0.023 (6)	−0.001 (4)	0.008 (5)	−0.005 (5)
C25	0.020 (5)	0.010 (5)	0.021 (6)	0.002 (4)	0.009 (5)	0.000 (4)
C26	0.015 (5)	0.016 (5)	0.022 (6)	0.005 (4)	0.006 (4)	−0.003 (4)
C27	0.022 (6)	0.038 (6)	0.016 (6)	−0.006 (4)	0.004 (5)	−0.001 (5)
N31	0.016 (4)	0.008 (4)	0.018 (5)	−0.001 (3)	−0.002 (4)	0.002 (4)
C32	0.022 (5)	0.020 (5)	0.018 (6)	−0.003 (4)	0.008 (5)	0.004 (5)
C33	0.034 (6)	0.013 (5)	0.018 (5)	0.007 (4)	0.008 (5)	0.001 (4)
C34	0.020 (5)	0.029 (7)	0.013 (6)	0.002 (4)	0.009 (5)	−0.001 (4)
C35	0.012 (5)	0.028 (6)	0.021 (6)	0.001 (4)	0.004 (4)	0.009 (5)
C36	0.022 (5)	0.016 (5)	0.019 (6)	−0.003 (4)	−0.001 (4)	0.009 (4)
C37	0.028 (6)	0.036 (7)	0.034 (7)	0.012 (5)	0.015 (5)	−0.009 (5)
N41	0.012 (4)	0.033 (5)	0.009 (4)	0.000 (3)	0.004 (4)	0.000 (4)
C42	0.021 (6)	0.034 (7)	0.024 (6)	0.012 (5)	0.008 (5)	−0.001 (5)
C43	0.031 (6)	0.018 (6)	0.020 (6)	0.011 (4)	0.006 (5)	0.000 (5)
C44	0.017 (5)	0.022 (5)	0.013 (5)	−0.004 (4)	−0.002 (4)	0.008 (4)
C45	0.030 (6)	0.014 (5)	0.016 (6)	0.002 (4)	0.006 (5)	−0.004 (4)
C46	0.021 (6)	0.031 (6)	0.029 (7)	−0.011 (5)	0.001 (5)	0.004 (5)
C47	0.043 (7)	0.031 (6)	0.013 (6)	−0.008 (5)	0.004 (5)	0.000 (5)
N51	0.024 (5)	0.016 (4)	0.020 (5)	−0.007 (3)	0.010 (4)	0.000 (4)
C52	0.035 (6)	0.015 (5)	0.029 (7)	−0.010 (4)	0.018 (5)	−0.006 (5)
C53	0.021 (6)	0.016 (5)	0.035 (7)	−0.003 (4)	0.014 (5)	−0.005 (5)
C54	0.018 (5)	0.018 (5)	0.028 (6)	0.001 (4)	0.010 (5)	0.008 (5)
C55	0.019 (5)	0.012 (5)	0.028 (6)	0.000 (4)	0.015 (5)	−0.003 (4)
C56	0.010 (5)	0.032 (6)	0.028 (7)	−0.001 (4)	0.006 (5)	0.011 (5)
C57	0.045 (7)	0.026 (6)	0.025 (7)	−0.003 (5)	0.018 (6)	0.002 (5)
N61	0.021 (5)	0.023 (5)	0.023 (5)	−0.002 (4)	0.011 (4)	−0.002 (4)
C62	0.033 (6)	0.018 (6)	0.048 (8)	−0.007 (5)	0.032 (6)	−0.005 (5)
C63	0.036 (7)	0.025 (6)	0.032 (6)	0.005 (5)	0.020 (6)	0.007 (5)
C64	0.026 (6)	0.030 (7)	0.026 (7)	0.003 (4)	0.017 (6)	0.001 (5)
C65	0.024 (5)	0.025 (5)	0.015 (5)	−0.010 (4)	0.016 (4)	−0.006 (4)
C66	0.017 (5)	0.006 (4)	0.025 (6)	0.000 (3)	0.008 (4)	−0.001 (4)
C67	0.034 (7)	0.040 (7)	0.029 (6)	0.008 (5)	0.009 (5)	0.017 (6)
C1	0.021 (6)	0.029 (6)	0.026 (7)	0.001 (4)	0.009 (5)	−0.005 (5)
Cl5	0.046 (2)	0.037 (2)	0.028 (2)	0.0022 (13)	0.0183 (17)	0.0111 (12)
Cl6	0.0321 (15)	0.0336 (15)	0.0241 (15)	0.0045 (11)	0.0099 (12)	0.0058 (12)
C2	0.016 (5)	0.021 (5)	0.032 (7)	−0.001 (4)	0.007 (5)	0.001 (5)
Cl7	0.0447 (19)	0.0321 (18)	0.037 (2)	0.0010 (12)	0.0266 (17)	−0.0001 (14)
Cl8	0.0232 (14)	0.0354 (15)	0.0258 (14)	−0.0068 (11)	0.0098 (11)	0.0026 (12)

Geometric parameters (Å, º)

Au1—N21	2.042 (8)	C37—H37C	0.9800
Au1—N11	2.061 (8)	N41—C46	1.471 (13)
Au1—Au2	3.3138 (6)	N41—C42	1.475 (13)
Au2—N31	2.078 (9)	N41—H41	0.81 (3)
Au2—Cl1	2.267 (3)	C42—C43	1.508 (14)
Au3—N41	2.051 (8)	C42—H42A	0.9900
Au3—N51	2.060 (9)	C42—H42B	0.9900
Au3—Au4	3.2619 (5)	C43—C44	1.529 (13)
Au4—N61	2.062 (9)	C43—H43A	0.9900
Au4—Cl2	2.261 (3)	C43—H43B	0.9900
N11—C16	1.486 (13)	C44—C45	1.493 (13)
N11—C12	1.507 (14)	C44—C47	1.530 (14)
N11—H11	0.82 (3)	C44—H44	1.0000
C12—C13	1.512 (14)	C45—C46	1.519 (15)
C12—H12A	0.9900	C45—H45A	0.9900
C12—H12B	0.9900	C45—H45B	0.9900
C13—C14	1.526 (13)	C46—H46A	0.9900
C13—H13A	0.9900	C46—H46B	0.9900
C13—H13B	0.9900	C47—H47A	0.9800
C14—C17	1.513 (14)	C47—H47B	0.9800
C14—C15	1.536 (14)	C47—H47C	0.9800
C14—H14	1.0000	N51—C56	1.478 (13)
C15—C16	1.509 (14)	N51—C52	1.486 (12)
C15—H15A	0.9900	N51—H51	0.81 (3)
C15—H15B	0.9900	C52—C53	1.527 (15)
C16—H16A	0.9900	C52—H52A	0.9900
C16—H16B	0.9900	C52—H52B	0.9900
C17—H17A	0.9800	C53—C54	1.520 (14)
C17—H17B	0.9800	C53—H53A	0.9900
C17—H17C	0.9800	C53—H53B	0.9900
N21—C22	1.497 (12)	C54—C57	1.519 (14)
N21—C26	1.502 (12)	C54—C55	1.543 (13)
N21—H21	0.81 (3)	C54—H54	1.0000
C22—C23	1.506 (14)	C55—C56	1.500 (14)
C22—H22A	0.9900	C55—H55A	0.9900
C22—H22B	0.9900	C55—H55B	0.9900
C23—C24	1.519 (14)	C56—H56A	0.9900
C23—H23A	0.9900	C56—H56B	0.9900
C23—H23B	0.9900	C57—H57A	0.9800
C24—C27	1.516 (14)	C57—H57B	0.9800
C24—C25	1.518 (13)	C57—H57C	0.9800
C24—H24	1.0000	N61—C66	1.467 (12)
C25—C26	1.501 (14)	N61—C62	1.494 (13)
C25—H25A	0.9900	N61—H61	0.81 (3)
C25—H25B	0.9900	C62—C63	1.550 (14)
C26—H26A	0.9900	C62—H62A	0.9900
C26—H26B	0.9900	C62—H62B	0.9900
C27—H27A	0.9800	C63—C64	1.520 (15)
C27—H27B	0.9800	C63—H63A	0.9900
C27—H27C	0.9800	C63—H63B	0.9900
N31—C36	1.492 (12)	C64—C67	1.523 (14)
N31—C32	1.512 (13)	C64—C65	1.543 (13)
N31—H31	0.82 (3)	C64—H64	1.0000
C32—C33	1.531 (13)	C65—C66	1.515 (12)
C32—H32A	0.9900	C65—H65A	0.9900
C32—H32B	0.9900	C65—H65B	0.9900
C33—C34	1.523 (14)	C66—H66A	0.9900
C33—H33A	0.9900	C66—H66B	0.9900
C33—H33B	0.9900	C67—H67A	0.9800
C34—C37	1.518 (13)	C67—H67B	0.9800
C34—C35	1.538 (13)	C67—H67C	0.9800
C34—H34	1.0000	C1—Cl6	1.726 (11)
C35—C36	1.522 (12)	C1—Cl5	1.796 (13)
C35—H35A	0.9900	C1—H1A	0.9900
C35—H35B	0.9900	C1—H1B	0.9900
C36—H36A	0.9900	C2—Cl7	1.738 (13)
C36—H36B	0.9900	C2—Cl8	1.777 (11)
C37—H37A	0.9800	C2—H2A	0.9900
C37—H37B	0.9800	C2—H2B	0.9900
N21—Au1—N11	176.2 (4)	C46—N41—C42	109.3 (8)
N21—Au1—Au2	97.4 (2)	C46—N41—Au3	115.1 (6)
N11—Au1—Au2	86.2 (3)	C42—N41—Au3	111.3 (7)
N31—Au2—Cl1	178.1 (2)	C46—N41—H41	109 (8)
N31—Au2—Au1	88.0 (2)	C42—N41—H41	110 (8)
Cl1—Au2—Au1	93.18 (6)	Au3—N41—H41	102 (7)
N41—Au3—N51	175.4 (3)	N41—C42—C43	110.4 (9)
N41—Au3—Au4	88.2 (3)	N41—C42—H42A	109.6
N51—Au3—Au4	96.1 (2)	C43—C42—H42A	109.6
N61—Au4—Cl2	178.1 (3)	N41—C42—H42B	109.6
N61—Au4—Au3	87.3 (2)	C43—C42—H42B	109.6
Cl2—Au4—Au3	94.52 (6)	H42A—C42—H42B	108.1
C16—N11—C12	108.6 (8)	C42—C43—C44	112.7 (9)
C16—N11—Au1	114.5 (6)	C42—C43—H43A	109.1
C12—N11—Au1	112.4 (7)	C44—C43—H43A	109.1
C16—N11—H11	111 (8)	C42—C43—H43B	109.1
C12—N11—H11	111 (8)	C44—C43—H43B	109.1
Au1—N11—H11	100 (7)	H43A—C43—H43B	107.8
N11—C12—C13	109.8 (8)	C45—C44—C43	110.8 (8)
N11—C12—H12A	109.7	C45—C44—C47	111.9 (9)
C13—C12—H12A	109.7	C43—C44—C47	111.1 (8)
N11—C12—H12B	109.7	C45—C44—H44	107.6
C13—C12—H12B	109.7	C43—C44—H44	107.6
H12A—C12—H12B	108.2	C47—C44—H44	107.6
C12—C13—C14	114.0 (9)	C44—C45—C46	111.9 (9)
C12—C13—H13A	108.7	C44—C45—H45A	109.2
C14—C13—H13A	108.7	C46—C45—H45A	109.2
C12—C13—H13B	108.7	C44—C45—H45B	109.2
C14—C13—H13B	108.7	C46—C45—H45B	109.2
H13A—C13—H13B	107.6	H45A—C45—H45B	107.9
C17—C14—C13	111.0 (8)	N41—C46—C45	110.8 (8)
C17—C14—C15	112.7 (9)	N41—C46—H46A	109.5
C13—C14—C15	110.1 (8)	C45—C46—H46A	109.5
C17—C14—H14	107.6	N41—C46—H46B	109.5
C13—C14—H14	107.6	C45—C46—H46B	109.5
C15—C14—H14	107.6	H46A—C46—H46B	108.1
C16—C15—C14	111.9 (9)	C44—C47—H47A	109.5
C16—C15—H15A	109.2	C44—C47—H47B	109.5
C14—C15—H15A	109.2	H47A—C47—H47B	109.5
C16—C15—H15B	109.2	C44—C47—H47C	109.5
C14—C15—H15B	109.2	H47A—C47—H47C	109.5
H15A—C15—H15B	107.9	H47B—C47—H47C	109.5
N11—C16—C15	111.5 (8)	C56—N51—C52	109.3 (8)
N11—C16—H16A	109.3	C56—N51—Au3	114.1 (6)
C15—C16—H16A	109.3	C52—N51—Au3	112.5 (7)
N11—C16—H16B	109.3	C56—N51—H51	106 (8)
C15—C16—H16B	109.3	C52—N51—H51	107 (8)
H16A—C16—H16B	108.0	Au3—N51—H51	108 (8)
C14—C17—H17A	109.5	N51—C52—C53	111.3 (9)
C14—C17—H17B	109.5	N51—C52—H52A	109.4
H17A—C17—H17B	109.5	C53—C52—H52A	109.4
C14—C17—H17C	109.5	N51—C52—H52B	109.4
H17A—C17—H17C	109.5	C53—C52—H52B	109.4
H17B—C17—H17C	109.5	H52A—C52—H52B	108.0
C22—N21—C26	110.1 (8)	C54—C53—C52	112.4 (9)
C22—N21—Au1	112.6 (6)	C54—C53—H53A	109.1
C26—N21—Au1	114.5 (6)	C52—C53—H53A	109.1
C22—N21—H21	110 (7)	C54—C53—H53B	109.1
C26—N21—H21	100 (7)	C52—C53—H53B	109.1
Au1—N21—H21	109 (7)	H53A—C53—H53B	107.8
N21—C22—C23	109.9 (8)	C57—C54—C53	111.8 (9)
N21—C22—H22A	109.7	C57—C54—C55	110.8 (9)
C23—C22—H22A	109.7	C53—C54—C55	109.6 (8)
N21—C22—H22B	109.7	C57—C54—H54	108.2
C23—C22—H22B	109.7	C53—C54—H54	108.2
H22A—C22—H22B	108.2	C55—C54—H54	108.2
C22—C23—C24	113.2 (9)	C56—C55—C54	112.3 (9)
C22—C23—H23A	108.9	C56—C55—H55A	109.2
C24—C23—H23A	108.9	C54—C55—H55A	109.2
C22—C23—H23B	108.9	C56—C55—H55B	109.2
C24—C23—H23B	108.9	C54—C55—H55B	109.2
H23A—C23—H23B	107.8	H55A—C55—H55B	107.9
C27—C24—C25	111.5 (9)	N51—C56—C55	111.5 (9)
C27—C24—C23	110.9 (9)	N51—C56—H56A	109.3
C25—C24—C23	110.7 (9)	C55—C56—H56A	109.3
C27—C24—H24	107.9	N51—C56—H56B	109.3
C25—C24—H24	107.9	C55—C56—H56B	109.3
C23—C24—H24	107.9	H56A—C56—H56B	108.0
C26—C25—C24	113.6 (9)	C54—C57—H57A	109.5
C26—C25—H25A	108.9	C54—C57—H57B	109.5
C24—C25—H25A	108.9	H57A—C57—H57B	109.5
C26—C25—H25B	108.9	C54—C57—H57C	109.5
C24—C25—H25B	108.9	H57A—C57—H57C	109.5
H25A—C25—H25B	107.7	H57B—C57—H57C	109.5
C25—C26—N21	108.8 (8)	C66—N61—C62	109.3 (8)
C25—C26—H26A	109.9	C66—N61—Au4	113.8 (6)
N21—C26—H26A	109.9	C62—N61—Au4	113.1 (7)
C25—C26—H26B	109.9	C66—N61—H61	116 (7)
N21—C26—H26B	109.9	C62—N61—H61	99 (7)
H26A—C26—H26B	108.3	Au4—N61—H61	105 (8)
C24—C27—H27A	109.5	N61—C62—C63	110.0 (8)
C24—C27—H27B	109.5	N61—C62—H62A	109.7
H27A—C27—H27B	109.5	C63—C62—H62A	109.7
C24—C27—H27C	109.5	N61—C62—H62B	109.7
H27A—C27—H27C	109.5	C63—C62—H62B	109.7
H27B—C27—H27C	109.5	H62A—C62—H62B	108.2
C36—N31—C32	110.0 (8)	C64—C63—C62	111.0 (9)
C36—N31—Au2	112.3 (6)	C64—C63—H63A	109.4
C32—N31—Au2	112.4 (6)	C62—C63—H63A	109.4
C36—N31—H31	124 (7)	C64—C63—H63B	109.4
C32—N31—H31	90 (7)	C62—C63—H63B	109.4
Au2—N31—H31	106 (7)	H63A—C63—H63B	108.0
N31—C32—C33	109.4 (8)	C63—C64—C67	108.7 (9)
N31—C32—H32A	109.8	C63—C64—C65	110.6 (10)
C33—C32—H32A	109.8	C67—C64—C65	111.2 (9)
N31—C32—H32B	109.8	C63—C64—H64	108.8
C33—C32—H32B	109.8	C67—C64—H64	108.8
H32A—C32—H32B	108.2	C65—C64—H64	108.8
C34—C33—C32	113.8 (8)	C66—C65—C64	111.2 (8)
C34—C33—H33A	108.8	C66—C65—H65A	109.4
C32—C33—H33A	108.8	C64—C65—H65A	109.4
C34—C33—H33B	108.8	C66—C65—H65B	109.4
C32—C33—H33B	108.8	C64—C65—H65B	109.4
H33A—C33—H33B	107.7	H65A—C65—H65B	108.0
C37—C34—C33	112.0 (9)	N61—C66—C65	110.6 (7)
C37—C34—C35	111.4 (9)	N61—C66—H66A	109.5
C33—C34—C35	109.4 (9)	C65—C66—H66A	109.5
C37—C34—H34	108.0	N61—C66—H66B	109.5
C33—C34—H34	108.0	C65—C66—H66B	109.5
C35—C34—H34	108.0	H66A—C66—H66B	108.1
C36—C35—C34	112.6 (8)	C64—C67—H67A	109.5
C36—C35—H35A	109.1	C64—C67—H67B	109.5
C34—C35—H35A	109.1	H67A—C67—H67B	109.5
C36—C35—H35B	109.1	C64—C67—H67C	109.5
C34—C35—H35B	109.1	H67A—C67—H67C	109.5
H35A—C35—H35B	107.8	H67B—C67—H67C	109.5
N31—C36—C35	110.8 (7)	Cl6—C1—Cl5	111.7 (6)
N31—C36—H36A	109.5	Cl6—C1—H1A	109.3
C35—C36—H36A	109.5	Cl5—C1—H1A	109.3
N31—C36—H36B	109.5	Cl6—C1—H1B	109.3
C35—C36—H36B	109.5	Cl5—C1—H1B	109.3
H36A—C36—H36B	108.1	H1A—C1—H1B	107.9
C34—C37—H37A	109.5	Cl7—C2—Cl8	112.1 (6)
C34—C37—H37B	109.5	Cl7—C2—H2A	109.2
H37A—C37—H37B	109.5	Cl8—C2—H2A	109.2
C34—C37—H37C	109.5	Cl7—C2—H2B	109.2
H37A—C37—H37C	109.5	Cl8—C2—H2B	109.2
H37B—C37—H37C	109.5	H2A—C2—H2B	107.9
C16—N11—C12—C13	60.7 (11)	C46—N41—C42—C43	−60.9 (11)
Au1—N11—C12—C13	−67.1 (10)	Au3—N41—C42—C43	67.3 (10)
N11—C12—C13—C14	−55.7 (11)	N41—C42—C43—C44	55.2 (12)
C12—C13—C14—C17	174.6 (9)	C42—C43—C44—C45	−49.4 (12)
C12—C13—C14—C15	49.1 (11)	C42—C43—C44—C47	−174.5 (9)
C17—C14—C15—C16	−173.3 (8)	C43—C44—C45—C46	49.7 (12)
C13—C14—C15—C16	−48.8 (11)	C47—C44—C45—C46	174.3 (8)
C12—N11—C16—C15	−62.6 (10)	C42—N41—C46—C45	62.0 (11)
Au1—N11—C16—C15	63.9 (9)	Au3—N41—C46—C45	−64.0 (10)
C14—C15—C16—N11	57.3 (11)	C44—C45—C46—N41	−57.2 (11)
C26—N21—C22—C23	−61.3 (10)	C56—N51—C52—C53	59.5 (11)
Au1—N21—C22—C23	67.9 (9)	Au3—N51—C52—C53	−68.4 (10)
N21—C22—C23—C24	55.0 (11)	N51—C52—C53—C54	−55.7 (12)
C22—C23—C24—C27	−173.0 (9)	C52—C53—C54—C57	173.2 (9)
C22—C23—C24—C25	−48.8 (12)	C52—C53—C54—C55	50.0 (12)
C27—C24—C25—C26	174.0 (8)	C57—C54—C55—C56	−174.7 (9)
C23—C24—C25—C26	50.1 (11)	C53—C54—C55—C56	−50.9 (11)
C24—C25—C26—N21	−56.7 (11)	C52—N51—C56—C55	−60.7 (11)
C22—N21—C26—C25	61.7 (10)	Au3—N51—C56—C55	66.3 (10)
Au1—N21—C26—C25	−66.4 (9)	C54—C55—C56—N51	57.3 (11)
C36—N31—C32—C33	59.5 (10)	C66—N61—C62—C63	−62.0 (11)
Au2—N31—C32—C33	−66.5 (9)	Au4—N61—C62—C63	65.8 (10)
N31—C32—C33—C34	−56.3 (12)	N61—C62—C63—C64	56.7 (13)
C32—C33—C34—C37	175.4 (9)	C62—C63—C64—C67	−173.6 (10)
C32—C33—C34—C35	51.4 (12)	C62—C63—C64—C65	−51.3 (13)
C37—C34—C35—C36	−175.3 (9)	C63—C64—C65—C66	52.1 (12)
C33—C34—C35—C36	−50.9 (12)	C67—C64—C65—C66	173.0 (9)
C32—N31—C36—C35	−60.6 (10)	C62—N61—C66—C65	63.2 (10)
Au2—N31—C36—C35	65.4 (9)	Au4—N61—C66—C65	−64.3 (9)
C34—C35—C36—N31	56.8 (11)	C64—C65—C66—N61	−58.3 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···Cl3	0.82 (3)	2.38 (4)	3.195 (9)	178 (11)
N21—H21···Cl3^i	0.81 (3)	2.45 (5)	3.229 (8)	161 (9)
N31—H31···Cl3	0.82 (3)	2.55 (6)	3.238 (8)	143 (8)
N41—H41···Cl4	0.81 (3)	2.43 (4)	3.234 (8)	172 (10)
N51—H51···Cl4^ii	0.81 (3)	2.42 (4)	3.209 (9)	165 (10)
N61—H61···Cl4	0.81 (3)	2.50 (6)	3.237 (9)	151 (9)
C1—H1B···Cl1	0.99	2.66	3.638 (11)	169
C1—H1A···Cl4	0.99	2.51	3.432 (11)	155
C2—H2A···Cl2	0.99	2.75	3.710 (11)	162
C2—H2B···Cl3^iii	0.99	2.59	3.431 (10)	143
C36—H36B···Au1^i	0.99	2.87	3.770 (9)	152
C16—H16A···Au2	0.99	2.71	3.562 (10)	144
C66—H66A···Au3^ii	0.99	2.91	3.778 (9)	147
C46—H46B···Au4	0.99	2.75	3.579 (11)	142
C34—H34···Cl1^iv	1.00	2.86	3.801 (13)	156
C64—H64···Cl2^v	1.00	2.81	3.755 (14)	158
C36—H36A···Cl3^i	0.99	2.88	3.571 (9)	127
C42—H42B···Cl3^i	0.99	2.95	3.828 (11)	148
C37—H37A···Cl5	0.98	2.90	3.701 (12)	140
C37—H37B···Cl6^iv	0.98	2.94	3.642 (12)	130
C47—H47C···Cl6^iv	0.98	2.77	3.595 (11)	142
C67—H67C···Cl7	0.98	2.95	3.770 (12)	142
C15—H15B···Cl8^vi	0.99	2.89	3.709 (11)	141
C17—H17B···Cl8^vi	0.98	2.80	3.637 (11)	143
C55—H55B···Cl8	0.99	2.94	3.872 (10)	158

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

Bis(2-methylpiperidine-κN)gold(I) chloride (5)

Crystal data

[Au(C6H13N)2]Cl	F(000) = 1664
Mr = 430.76	Dx = 1.896 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.6978 (7) Å	Cell parameters from 10304 reflections
b = 11.2748 (5) Å	θ = 2.2–30.9°
c = 16.5620 (6) Å	µ = 9.90 mm^−1
β = 114.013 (5)°	T = 100 K
V = 3018.8 (2) Å^3	Prism, colourless
Z = 8	0.2 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	4576 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3012 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.051
ω scan	θmax = 31.0°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	h = −24→24
Tmin = 0.472, Tmax = 1.000	k = −16→16
56753 measured reflections	l = −23→23

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)] = 0.029	Hydrogen site location: mixed
wR(F^2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0126P)^2 + 14.3004P] where P = (Fo^2 + 2Fc^2)/3
4576 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 2.19 e Å^−3
1 restraint	Δρmin = −0.93 e Å^−3

Special details

Geometry. Additional structural data:

H bonding angle at Cl1: 75.38 ( 1.57) H01 - Cl1 - H02

Torsion angles:

-51.28 ( 0.54) C12 - N11 - N11_$1 - C12_$1 74.61 ( 0.32) C12 - N11 - N11_$1 - C16_$1 74.61 ( 0.32) C16 - N11 - N11_$1 - C12_$1 -159.50 ( 0.50) C16 - N11 - N11_$1 - C16_$1 -15.23 ( 0.57) C22 - N21 - N21_$1 - C22_$1 112.02 ( 0.33) C22 - N21 - N21_$1 - C26_$1 112.02 ( 0.33) C26 - N21 - N21_$1 - C22_$1 -120.74 ( 0.55) C26 - N21 - N21_$1 - C26_$1

Symmetry operator: $1 1-x, y, 0.5-z

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

	x	y	z	Uiso*/Ueq
Au1	0.500000	0.65143 (2)	0.250000	0.01876 (6)
Au2	0.500000	0.35117 (2)	0.250000	0.02050 (6)
Cl1	0.67903 (7)	0.47503 (9)	0.49927 (7)	0.0351 (3)
N11	0.5458 (2)	0.6563 (3)	0.3855 (2)	0.0230 (7)
H01	0.580 (2)	0.605 (3)	0.404 (3)	0.008 (10)*
C12	0.5930 (3)	0.7669 (4)	0.4251 (3)	0.0304 (10)
H12	0.619005	0.756294	0.490706	0.037*
C13	0.5343 (4)	0.8710 (4)	0.4048 (3)	0.0409 (12)
H13A	0.511008	0.886761	0.340446	0.049*
H13B	0.565607	0.942291	0.435336	0.049*
C14	0.4640 (4)	0.8502 (5)	0.4332 (4)	0.0489 (14)
H14A	0.486069	0.848206	0.498521	0.059*
H14B	0.424028	0.916594	0.412179	0.059*
C15	0.4203 (3)	0.7355 (5)	0.3964 (3)	0.0421 (12)
H15A	0.378272	0.720215	0.420272	0.050*
H15B	0.391556	0.741606	0.331276	0.050*
C16	0.4805 (3)	0.6345 (4)	0.4200 (3)	0.0321 (10)
H16A	0.450750	0.560046	0.394545	0.039*
H16B	0.507020	0.625443	0.485098	0.039*
C17	0.6612 (3)	0.7837 (5)	0.3944 (3)	0.0410 (13)
H17A	0.692056	0.709351	0.401775	0.062*
H17B	0.698704	0.846202	0.429470	0.062*
H17C	0.637539	0.806470	0.331875	0.062*
N21	0.6268 (2)	0.3476 (3)	0.3152 (2)	0.0254 (7)
H02	0.635 (3)	0.385 (4)	0.359 (3)	0.038 (15)*
C22	0.6615 (3)	0.2274 (4)	0.3441 (3)	0.0323 (10)
H22	0.722096	0.236541	0.381045	0.039*
C23	0.6517 (3)	0.1515 (4)	0.2636 (3)	0.0385 (11)
H23A	0.679751	0.074390	0.283897	0.046*
H23B	0.592258	0.135776	0.228271	0.046*
C24	0.6881 (3)	0.2127 (5)	0.2056 (3)	0.0467 (14)
H24A	0.749179	0.213737	0.236952	0.056*
H24B	0.673745	0.166454	0.150513	0.056*
C25	0.6573 (3)	0.3380 (5)	0.1823 (3)	0.0428 (12)
H25A	0.597619	0.336758	0.143016	0.051*
H25B	0.687020	0.376581	0.150080	0.051*
C26	0.6706 (3)	0.4085 (5)	0.2647 (3)	0.0357 (11)
H26A	0.648562	0.489794	0.248173	0.043*
H26B	0.730526	0.414383	0.302433	0.043*
C27	0.6239 (3)	0.1748 (5)	0.4001 (3)	0.0410 (12)
H27A	0.625069	0.232562	0.444791	0.062*
H27B	0.655037	0.103917	0.429337	0.062*
H27C	0.566468	0.152896	0.363420	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01855 (13)	0.01891 (12)	0.01442 (13)	0.000	0.00220 (10)	0.000
Au2	0.01296 (12)	0.02646 (13)	0.01988 (14)	0.000	0.00442 (11)	0.000
Cl1	0.0340 (5)	0.0342 (7)	0.0243 (5)	0.0089 (4)	−0.0014 (4)	−0.0024 (4)
N11	0.0233 (17)	0.0216 (17)	0.0199 (16)	0.0011 (15)	0.0044 (14)	0.0024 (15)
C12	0.036 (2)	0.033 (2)	0.019 (2)	−0.012 (2)	0.0077 (18)	−0.0035 (18)
C13	0.069 (4)	0.022 (2)	0.038 (3)	−0.004 (2)	0.028 (3)	−0.0012 (19)
C14	0.062 (4)	0.049 (3)	0.047 (3)	0.011 (3)	0.034 (3)	0.003 (3)
C15	0.037 (3)	0.067 (4)	0.025 (2)	0.005 (3)	0.016 (2)	0.003 (2)
C16	0.032 (2)	0.041 (3)	0.021 (2)	−0.012 (2)	0.0074 (18)	0.0022 (19)
C17	0.032 (3)	0.064 (3)	0.026 (3)	−0.021 (2)	0.011 (2)	−0.011 (2)
N21	0.0184 (16)	0.034 (2)	0.0215 (17)	−0.0005 (16)	0.0061 (14)	−0.0041 (17)
C22	0.026 (2)	0.038 (3)	0.030 (2)	0.008 (2)	0.008 (2)	0.005 (2)
C23	0.034 (3)	0.035 (3)	0.040 (3)	0.004 (2)	0.009 (2)	0.000 (2)
C24	0.040 (3)	0.072 (4)	0.029 (3)	0.006 (3)	0.015 (2)	−0.002 (3)
C25	0.033 (3)	0.066 (4)	0.033 (3)	0.004 (3)	0.017 (2)	0.005 (3)
C26	0.021 (2)	0.054 (3)	0.030 (2)	−0.004 (2)	0.0096 (19)	0.001 (2)
C27	0.034 (3)	0.045 (3)	0.043 (3)	0.007 (2)	0.014 (2)	0.012 (2)

Geometric parameters (Å, º)

Au1—N11^i	2.053 (3)	C14—H14A	0.9900
Au1—N11	2.053 (3)	C14—H14B	0.9900
Au1—Au2	3.3854 (3)	C15—H15A	0.9900
Au2—N21	2.057 (3)	C15—H15B	0.9900
Au2—N21^i	2.057 (3)	C16—H16A	0.9900
N11—C12	1.496 (5)	C16—H16B	0.9900
N11—C16	1.503 (6)	C17—H17A	0.9800
C12—C17	1.501 (6)	C17—H17B	0.9800
C12—C13	1.512 (7)	C17—H17C	0.9800
C13—C14	1.518 (7)	N21—H02	0.80 (3)
C14—C15	1.503 (8)	C22—H22	1.0000
C15—C16	1.498 (7)	C23—H23A	0.9900
N21—C22	1.485 (6)	C23—H23B	0.9900
N21—C26	1.517 (6)	C24—H24A	0.9900
C22—C27	1.469 (7)	C24—H24B	0.9900
C22—C23	1.534 (7)	C25—H25A	0.9900
C23—C24	1.521 (7)	C25—H25B	0.9900
C24—C25	1.507 (7)	C26—H26A	0.9900
C25—C26	1.512 (7)	C26—H26B	0.9900
N11—H01	0.80 (3)	C27—H27A	0.9800
C12—H12	1.0000	C27—H27B	0.9800
C13—H13A	0.9900	C27—H27C	0.9800
C13—H13B	0.9900
N11^i—Au1—N11	176.9 (2)	C14—C15—H15B	109.5
N11^i—Au1—Au2	91.54 (10)	H15A—C15—H15B	108.1
N11—Au1—Au2	91.54 (10)	C15—C16—H16A	109.5
N21—Au2—N21^i	177.8 (2)	N11—C16—H16A	109.5
N21—Au2—Au1	91.11 (11)	C15—C16—H16B	109.5
N21^i—Au2—Au1	91.11 (11)	N11—C16—H16B	109.5
C12—N11—C16	110.4 (3)	H16A—C16—H16B	108.1
C12—N11—Au1	113.8 (3)	C12—C17—H17A	109.5
C16—N11—Au1	112.9 (3)	C12—C17—H17B	109.5
N11—C12—C17	109.9 (4)	H17A—C17—H17B	109.5
N11—C12—C13	109.8 (4)	C12—C17—H17C	109.5
C17—C12—C13	113.7 (4)	H17A—C17—H17C	109.5
C12—C13—C14	112.8 (4)	H17B—C17—H17C	109.5
C15—C14—C13	111.0 (4)	C22—N21—H02	107 (4)
C16—C15—C14	110.8 (4)	C26—N21—H02	109 (4)
C15—C16—N11	110.5 (4)	Au2—N21—H02	103 (4)
C22—N21—C26	110.6 (4)	C27—C22—H22	107.7
C22—N21—Au2	114.0 (3)	N21—C22—H22	107.7
C26—N21—Au2	113.3 (3)	C23—C22—H22	107.7
C27—C22—N21	109.7 (4)	C24—C23—H23A	109.3
C27—C22—C23	113.8 (4)	C22—C23—H23A	109.3
N21—C22—C23	110.1 (4)	C24—C23—H23B	109.3
C24—C23—C22	111.6 (4)	C22—C23—H23B	109.3
C25—C24—C23	112.6 (4)	H23A—C23—H23B	108.0
C24—C25—C26	110.8 (4)	C25—C24—H24A	109.1
C25—C26—N21	109.4 (4)	C23—C24—H24A	109.1
C12—N11—H01	104 (3)	C25—C24—H24B	109.1
C16—N11—H01	108 (3)	C23—C24—H24B	109.1
Au1—N11—H01	107 (3)	H24A—C24—H24B	107.8
N11—C12—H12	107.8	C24—C25—H25A	109.5
C17—C12—H12	107.8	C26—C25—H25A	109.5
C13—C12—H12	107.8	C24—C25—H25B	109.5
C12—C13—H13A	109.0	C26—C25—H25B	109.5
C14—C13—H13A	109.0	H25A—C25—H25B	108.1
C12—C13—H13B	109.0	C25—C26—H26A	109.8
C14—C13—H13B	109.0	N21—C26—H26A	109.8
H13A—C13—H13B	107.8	C25—C26—H26B	109.8
C15—C14—H14A	109.4	N21—C26—H26B	109.8
C13—C14—H14A	109.4	H26A—C26—H26B	108.2
C15—C14—H14B	109.4	C22—C27—H27A	109.5
C13—C14—H14B	109.4	C22—C27—H27B	109.5
H14A—C14—H14B	108.0	H27A—C27—H27B	109.5
C16—C15—H15A	109.5	C22—C27—H27C	109.5
C14—C15—H15A	109.5	H27A—C27—H27C	109.5
C16—C15—H15B	109.5	H27B—C27—H27C	109.5
N11—Au1—Au2—N21^i	115.79 (14)	C13—C14—C15—C16	53.9 (6)
N11^i—Au1—Au2—N21^i	−64.21 (14)	C14—C15—C16—N11	−58.4 (5)
N11—Au1—Au2—N21	−64.21 (14)	C12—N11—C16—C15	60.7 (5)
N11^i—Au1—Au2—N21	115.79 (14)	Au1—N11—C16—C15	−67.9 (4)
Au2—Au1—N11—C12	154.1 (3)	C26—N21—C22—C27	174.5 (4)
Au2—Au1—N11—C16	−79.1 (3)	Au2—N21—C22—C27	−56.4 (5)
Au1—Au2—N21—C22	172.3 (3)	C26—N21—C22—C23	−59.5 (5)
Au1—Au2—N21—C26	−60.0 (3)	Au2—N21—C22—C23	69.6 (4)
C16—N11—C12—C17	176.6 (4)	C27—C22—C23—C24	177.3 (4)
Au1—N11—C12—C17	−55.3 (4)	N21—C22—C23—C24	53.7 (5)
C16—N11—C12—C13	−57.7 (4)	C22—C23—C24—C25	−50.9 (6)
Au1—N11—C12—C13	70.4 (4)	C23—C24—C25—C26	53.3 (6)
N11—C12—C13—C14	54.2 (5)	C24—C25—C26—N21	−57.8 (5)
C17—C12—C13—C14	177.8 (4)	C22—N21—C26—C25	61.9 (5)
C12—C13—C14—C15	−52.5 (6)	Au2—N21—C26—C25	−67.5 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H01···Cl1	0.80 (3)	2.34 (3)	3.110 (4)	162 (4)
N21—H02···Cl1	0.80 (3)	2.36 (3)	3.149 (4)	170 (5)
C27—H27A···Cl1	0.98	2.92	3.715 (6)	140
C17—H17B···Cl1^ii	0.98	2.84	3.800 (5)	167
C25—H25B···Cl1^iii	0.99	2.96	3.839 (5)	148
C27—H27B···Cl1^iv	0.98	2.83	3.615 (5)	138
C13—H13A···Au1	0.99	3.01	3.436 (5)	107
C15—H15B···Au1	0.99	2.94	3.398 (5)	109
C17—H17C···Au1	0.98	2.85	3.245 (5)	105
C23—H23B···Au2	0.99	3.03	3.440 (5)	106
C25—H25A···Au2	0.99	2.94	3.401 (5)	110
C27—H27C···Au2	0.98	2.85	3.241 (5)	105

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