#------------------------------------------------------------------------------
#$Date: 2024-03-05 22:43:10 +0200 (Tue, 05 Mar 2024) $
#$Revision: 290331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023013
loop_
_publ_author_name
'Döring, Cindy'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structures of five gold(I) complexes with methyl-piperidine
 ligands.
;
_journal_coeditor_code           YZ2046
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              157
_journal_page_last               165
_journal_paper_doi               10.1107/S2056989023010940
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          '[Au (C6 H13 N)2] [Au Cl2]'
_chemical_formula_moiety         'C12 H26 Au N2 +, Au Cl2 -'
_chemical_formula_sum            'C12 H26 Au2 Cl2 N2'
_chemical_formula_weight         663.18
_chemical_name_systematic
;
Bis(4-methylpiperidine-κN)gold(I) dichloridoaurate(I)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.218(6)
_cell_angle_beta                 101.893(5)
_cell_angle_gamma                114.695(8)
_cell_formula_units_Z            2
_cell_length_a                   9.6998(7)
_cell_length_b                   9.7001(8)
_cell_length_c                   10.7194(5)
_cell_measurement_reflns_used    20172
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8327
_cell_measurement_theta_min      2.4448
_cell_volume                     844.89(13)
_computing_cell_refinement
;
CrysAlisPro, Version 1.171.35.21. Rigaku OD (2020)
;
_computing_data_collection
;
CrysAlisPro, Version 1.171.35.21. Rigaku OD (2020)
;
_computing_data_reduction
;
CrysAlisPro, Version 1.171.35.21. Rigaku OD (2020)
;
_computing_molecular_graphics
;
Siemens XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL-2018/3 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL-2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            54252
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.016
_diffrn_reflns_theta_min         2.450
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    17.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.017
_refine_diff_density_min         -2.524
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4874
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0107P)²+9.0373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0635
_reflns_number_gt                4690
_reflns_number_total             4874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2046sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2023012--2023016.cif.'
_cod_original_cell_volume        844.89(11)
_cod_database_code               2023013
_cod_database_fobs_code          2023013
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.177
_shelx_estimated_absorpt_t_max   0.620
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au Au1 0.34494(3) 0.35477(3) 0.15546(3) 0.01219(6) Uani d 1 . .
Au Au2 0.61479(3) 0.67852(3) 0.13899(3) 0.01717(7) Uani d 1 . .
Cl Cl1 0.8285(2) 0.6453(3) 0.2297(2) 0.0231(4) Uani d 1 . .
Cl Cl2 0.4149(2) 0.7390(2) 0.0684(2) 0.0198(4) Uani d 1 . .
N N11 0.5267(7) 0.3046(7) 0.2280(6) 0.0112(11) Uani d 1 . .
H H01 0.606(9) 0.357(10) 0.190(8) 0.01(2) Uiso d 1 . .
C C12 0.4725(9) 0.1288(9) 0.1908(8) 0.0160(14) Uani d 1 . .
H H12A 0.566659 0.111854 0.217324 0.019 Uiso calc 1 . .
H H12B 0.419603 0.076605 0.091666 0.019 Uiso calc 1 . .
C C13 0.3549(9) 0.0532(9) 0.2624(8) 0.0162(14) Uani d 1 . .
H H13A 0.322562 -0.062807 0.239218 0.019 Uiso calc 1 . .
H H13B 0.257095 0.062502 0.229561 0.019 Uiso calc 1 . .
C C14 0.4282(10) 0.1339(10) 0.4167(8) 0.0179(15) Uani d 1 . .
H H14 0.518867 0.112370 0.449831 0.022 Uiso calc 1 . .
C C15 0.4954(9) 0.3159(9) 0.4524(7) 0.0157(14) Uani d 1 . .
H H15A 0.405314 0.339488 0.428818 0.019 Uiso calc 1 . .
H H15B 0.551936 0.368507 0.551193 0.019 Uiso calc 1 . .
C C16 0.6112(9) 0.3857(9) 0.3783(8) 0.0168(15) Uani d 1 . .
H H16A 0.650234 0.503004 0.402217 0.020 Uiso calc 1 . .
H H16B 0.705164 0.368771 0.405836 0.020 Uiso calc 1 . .
C C17 0.3025(11) 0.0634(11) 0.4841(9) 0.0271(19) Uani d 1 . .
H H17A 0.352868 0.111307 0.582603 0.041 Uiso calc 1 . .
H H17B 0.259608 -0.053520 0.457264 0.041 Uiso calc 1 . .
H H17C 0.214780 0.087344 0.455363 0.041 Uiso calc 1 . .
N N21 0.1546(7) 0.3937(7) 0.0850(6) 0.0127(12) Uani d 1 . .
H H02 0.182(13) 0.453(12) 0.025(9) 0.03(3) Uiso d 1 . .
C C22 0.0007(9) 0.2393(10) 0.0106(8) 0.0196(15) Uani d 1 . .
H H22A 0.015903 0.171266 -0.062462 0.023 Uiso calc 1 . .
H H22B -0.084368 0.262574 -0.031300 0.023 Uiso calc 1 . .
C C23 -0.0507(9) 0.1495(10) 0.1071(9) 0.0209(16) Uani d 1 . .
H H23A 0.030961 0.119174 0.143159 0.025 Uiso calc 1 . .
H H23B -0.153749 0.049084 0.056799 0.025 Uiso calc 1 . .
C C24 -0.0713(9) 0.2496(10) 0.2247(8) 0.0194(16) Uani d 1 . .
H H24 -0.164643 0.265908 0.187621 0.023 Uiso calc 1 . .
C C25 0.0786(9) 0.4153(10) 0.2927(8) 0.0184(15) Uani d 1 . .
H H25A 0.057033 0.483991 0.359758 0.022 Uiso calc 1 . .
H H25B 0.168456 0.402692 0.341894 0.022 Uiso calc 1 . .
C C26 0.1285(9) 0.4984(9) 0.1924(8) 0.0174(15) Uani d 1 . .
H H26A 0.043789 0.521809 0.149634 0.021 Uiso calc 1 . .
H H26B 0.228953 0.601968 0.240362 0.021 Uiso calc 1 . .
C C27 -0.1075(11) 0.1642(12) 0.3275(10) 0.0276(19) Uani d 1 . .
H H27A -0.207149 0.061261 0.283271 0.041 Uiso calc 1 . .
H H27B -0.119850 0.231831 0.401554 0.041 Uiso calc 1 . .
H H27C -0.018602 0.144513 0.363625 0.041 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N21 Au1 N11 . . 176.8(2) y
N21 Au1 Au2 . . 95.61(17) y
N11 Au1 Au2 . . 87.59(17) y
N21 Au1 Au2 . 2_665 87.50(18) y
N11 Au1 Au2 . 2_665 94.13(17) y
Au2 Au1 Au2 . 2_665 66.011(12) y
Cl1 Au2 Cl2 . . 173.42(7) y
Cl1 Au2 Au1 . . 96.01(5) y
Cl2 Au2 Au1 . . 87.38(5) y
Cl1 Au2 Au1 . 2_665 95.47(5) y
Cl2 Au2 Au1 . 2_665 88.25(5) y
Au1 Au2 Au1 . 2_665 113.989(13) y
Cl1 Au2 Au2 . 2_665 100.58(6) ?
Cl2 Au2 Au2 . 2_665 85.99(5) ?
Au1 Au2 Au2 . 2_665 57.208(12) ?
Au1 Au2 Au2 2_665 2_665 56.781(11) ?
C12 N11 C16 . . 110.0(6) ?
C12 N11 Au1 . . 113.2(4) ?
C16 N11 Au1 . . 113.2(5) ?
N11 C12 C13 . . 110.0(6) ?
C12 C13 C14 . . 112.1(6) ?
C15 C14 C17 . . 111.4(7) ?
C15 C14 C13 . . 109.5(6) ?
C17 C14 C13 . . 110.5(7) ?
C16 C15 C14 . . 112.0(6) ?
N11 C16 C15 . . 109.5(6) ?
C22 N21 C26 . . 109.1(6) ?
C22 N21 Au1 . . 112.1(5) ?
C26 N21 Au1 . . 114.3(5) ?
N21 C22 C23 . . 110.2(6) ?
C22 C23 C24 . . 112.3(7) ?
C23 C24 C27 . . 111.7(7) ?
C23 C24 C25 . . 110.2(6) ?
C27 C24 C25 . . 110.7(7) ?
C26 C25 C24 . . 112.6(7) ?
N21 C26 C25 . . 110.5(6) ?
C12 N11 H01 . . 112(5) ?
C16 N11 H01 . . 104(5) ?
Au1 N11 H01 . . 104(5) ?
N11 C12 H12A . . 109.7 ?
C13 C12 H12A . . 109.7 ?
N11 C12 H12B . . 109.7 ?
C13 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C15 C14 H14 . . 108.5 ?
C17 C14 H14 . . 108.5 ?
C13 C14 H14 . . 108.5 ?
C16 C15 H15A . . 109.2 ?
C14 C15 H15A . . 109.2 ?
C16 C15 H15B . . 109.2 ?
C14 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
N11 C16 H16A . . 109.8 ?
C15 C16 H16A . . 109.8 ?
N11 C16 H16B . . 109.8 ?
C15 C16 H16B . . 109.8 ?
H16A C16 H16B . . 108.2 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C22 N21 H02 . . 110(7) ?
C26 N21 H02 . . 105(7) ?
Au1 N21 H02 . . 106(7) ?
N21 C22 H22A . . 109.6 ?
C23 C22 H22A . . 109.6 ?
N21 C22 H22B . . 109.6 ?
C23 C22 H22B . . 109.6 ?
H22A C22 H22B . . 108.1 ?
C22 C23 H23A . . 109.1 ?
C24 C23 H23A . . 109.1 ?
C22 C23 H23B . . 109.1 ?
C24 C23 H23B . . 109.1 ?
H23A C23 H23B . . 107.9 ?
C23 C24 H24 . . 108.0 ?
C27 C24 H24 . . 108.0 ?
C25 C24 H24 . . 108.0 ?
C26 C25 H25A . . 109.1 ?
C24 C25 H25A . . 109.1 ?
C26 C25 H25B . . 109.1 ?
C24 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.8 ?
N21 C26 H26A . . 109.6 ?
C25 C26 H26A . . 109.6 ?
N21 C26 H26B . . 109.6 ?
C25 C26 H26B . . 109.6 ?
H26A C26 H26B . . 108.1 ?
C24 C27 H27A . . 109.5 ?
C24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Au1 N21 . 2.062(7) y
Au1 N11 . 2.064(6) y
Au1 Au2 . 3.2096(5) y
Au1 Au2 2_665 3.2252(4) y
Au2 Cl1 . 2.282(2) y
Au2 Cl2 . 2.282(2) y
N11 C12 . 1.490(9) ?
N11 C16 . 1.506(9) ?
C12 C13 . 1.525(10) ?
C13 C14 . 1.535(11) ?
C14 C15 . 1.529(10) ?
C14 C17 . 1.533(11) ?
C15 C16 . 1.520(10) ?
N21 C22 . 1.498(9) ?
N21 C26 . 1.504(10) ?
C22 C23 . 1.520(11) ?
C23 C24 . 1.523(12) ?
C24 C27 . 1.525(11) ?
C24 C25 . 1.531(11) ?
C25 C26 . 1.516(11) ?
N11 H01 . 0.95(6) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14 . 1.0000 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
N21 H02 . 0.95(6) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 H24 . 1.0000 ?
C25 H25A . 0.9900 ?
C25 H25B . 0.9900 ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N11 H01 Cl1 . 0.95(6) 2.59(7) 3.370(6) 139(7) yes
N11 H01 Cl2 2_665 0.95(6) 2.66(8) 3.312(7) 126(6) yes
N21 H02 Cl2 . 0.95(6) 2.61(9) 3.316(7) 131(8) yes
N21 H02 Cl1 2_665 0.95(6) 2.66(9) 3.360(7) 130(8) yes
C13 H13A Cl2 1_545 0.99 2.91 3.640(8) 131.1 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 N11 C12 C13 . . . . 60.8(8) ?
Au1 N11 C12 C13 . . . . -66.9(7) y
N11 C12 C13 C14 . . . . -57.1(8) ?
C12 C13 C14 C15 . . . . 52.6(8) ?
C12 C13 C14 C17 . . . . 175.7(7) y
C17 C14 C15 C16 . . . . -175.9(7) y
C13 C14 C15 C16 . . . . -53.4(8) ?
C12 N11 C16 C15 . . . . -61.3(8) ?
Au1 N11 C16 C15 . . . . 66.4(7) y
C14 C15 C16 N11 . . . . 58.1(8) ?
C26 N21 C22 C23 . . . . -61.3(8) ?
Au1 N21 C22 C23 . . . . 66.3(7) y
N21 C22 C23 C24 . . . . 57.5(8) ?
C22 C23 C24 C27 . . . . -174.6(7) y
C22 C23 C24 C25 . . . . -51.2(9) ?
C23 C24 C25 C26 . . . . 50.6(9) ?
C27 C24 C25 C26 . . . . 174.6(7) y
C22 N21 C26 C25 . . . . 60.7(8) ?
Au1 N21 C26 C25 . . . . -65.7(7) y
C24 C25 C26 N21 . . . . -56.1(9) ?
