#------------------------------------------------------------------------------
#$Date: 2024-03-05 22:43:10 +0200 (Tue, 05 Mar 2024) $
#$Revision: 290331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023014.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_2023014
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 Br2]'
_chemical_formula_moiety         'C12 H26 Au N2 +, Au Br2 -'
_chemical_formula_sum            'C12 H26 Au2 Br2 N2'
_chemical_formula_weight         752.10
_chemical_name_systematic
;
Bis(4-methylpiperidine-κN)gold(I) dibromidoaurate(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                100.136(4)
_cell_angle_beta                 103.685(5)
_cell_angle_gamma                116.287(5)
_cell_formula_units_Z            2
_cell_length_a                   9.8461(6)
_cell_length_b                   9.7728(4)
_cell_length_c                   10.9461(5)
_cell_measurement_reflns_used    12875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3270
_cell_measurement_theta_min      2.5690
_cell_volume                     868.58(10)
_computing_cell_refinement
;
CrysAlisPro, Version 1.171.36.28. Rigaku OD (2020)
;
_computing_data_collection
;
CrysAlisPro, Version 1.171.36.28. Rigaku OD (2020)
;
_computing_data_reduction
;
CrysAlisPro, Version 1.171.36.28. 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 0.989
_diffrn_measured_fraction_theta_max 0.941
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            48187
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.970
_diffrn_reflns_theta_min         2.446
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    21.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.876
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.020
_refine_diff_density_min         -1.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         5188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0127P)²+1.3346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0385
_refine_ls_wR_factor_ref         0.0409
_reflns_number_gt                4466
_reflns_number_total             5188
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2046sup1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 2023012--2023016.cif.'
_cod_original_cell_volume        868.59(9)
_cod_database_code               2023014
_cod_database_fobs_code          2023014
_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   0.279
_shelx_estimated_absorpt_t_max   0.413
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 0.34246(2) 0.35042(2) 0.15864(2) 0.01326(4) Uani d 1 . .
Au Au2 0.62704(2) 0.68148(2) 0.13846(2) 0.01800(4) Uani d 1 . .
Br Br1 0.85675(5) 0.65879(5) 0.24231(4) 0.02139(8) Uani d 1 . .
Br Br2 0.42027(5) 0.74623(5) 0.06245(4) 0.01870(8) Uani d 1 . .
N N11 0.5261(4) 0.3083(4) 0.2396(3) 0.0146(6) Uani d 1 . .
H H01 0.597(5) 0.352(5) 0.199(4) 0.031(13) Uiso d 1 . .
C C12 0.4724(5) 0.1335(4) 0.2092(4) 0.0174(8) Uani d 1 . .
H H12A 0.568195 0.120983 0.238943 0.021 Uiso calc 1 . .
H H12B 0.418198 0.078799 0.112095 0.021 Uiso calc 1 . .
C C13 0.3569(5) 0.0555(4) 0.2781(4) 0.0172(8) Uani d 1 . .
H H13A 0.326771 -0.059071 0.259395 0.021 Uiso calc 1 . .
H H13B 0.256719 0.058865 0.241634 0.021 Uiso calc 1 . .
C C14 0.4302(5) 0.1390(5) 0.4283(4) 0.0187(8) Uani d 1 . .
H H14 0.522920 0.122592 0.465036 0.022 Uiso calc 1 . .
C C15 0.4963(5) 0.3198(4) 0.4574(4) 0.0170(8) Uani d 1 . .
H H15A 0.404566 0.338866 0.430613 0.020 Uiso calc 1 . .
H H15B 0.554663 0.375071 0.554164 0.020 Uiso calc 1 . .
C C16 0.6104(4) 0.3918(4) 0.3849(3) 0.0158(7) Uani d 1 . .
H H16A 0.647748 0.508115 0.404629 0.019 Uiso calc 1 . .
H H16B 0.706631 0.380388 0.416039 0.019 Uiso calc 1 . .
C C17 0.3069(5) 0.0671(5) 0.4946(4) 0.0272(9) Uani d 1 . .
H H17A 0.359292 0.118548 0.591142 0.041 Uiso calc 1 . .
H H17B 0.265399 -0.049068 0.472803 0.041 Uiso calc 1 . .
H H17C 0.216830 0.085712 0.462499 0.041 Uiso calc 1 . .
N N21 0.1493(4) 0.3816(4) 0.0822(3) 0.0151(6) Uani d 1 . .
H H02 0.171(6) 0.430(5) 0.021(4) 0.033(13) Uiso d 1 . .
C C22 -0.0056(5) 0.2246(5) 0.0142(4) 0.0194(8) Uani d 1 . .
H H22A 0.007975 0.154374 -0.053028 0.023 Uiso calc 1 . .
H H22B -0.091892 0.243355 -0.032194 0.023 Uiso calc 1 . .
C C23 -0.0549(5) 0.1417(5) 0.1134(4) 0.0226(8) Uani d 1 . .
H H23A 0.027452 0.115019 0.153904 0.027 Uiso calc 1 . .
H H23B -0.159362 0.039296 0.066307 0.027 Uiso calc 1 . .
C C24 -0.0728(5) 0.2453(5) 0.2231(4) 0.0207(8) Uani d 1 . .
H H24 -0.166501 0.258762 0.182547 0.025 Uiso calc 1 . .
C C25 0.0802(5) 0.4118(5) 0.2853(4) 0.0184(8) Uani d 1 . .
H H25A 0.061751 0.482870 0.347349 0.022 Uiso calc 1 . .
H H25B 0.170552 0.401935 0.337243 0.022 Uiso calc 1 . .
C C26 0.1279(5) 0.4885(5) 0.1823(4) 0.0180(8) Uani d 1 . .
H H26A 0.042993 0.509416 0.136656 0.022 Uiso calc 1 . .
H H26B 0.230477 0.593130 0.226770 0.022 Uiso calc 1 . .
C C27 -0.1067(5) 0.1650(6) 0.3281(5) 0.0303(10) Uani d 1 . .
H H27A -0.205630 0.058909 0.286356 0.045 Uiso calc 1 . .
H H27B -0.121036 0.232218 0.395758 0.045 Uiso calc 1 . .
H H27C -0.015303 0.152108 0.369797 0.045 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'
Br Br -0.2901 2.4595 '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
N11 Au1 N21 . . 176.30(13) y
N11 Au1 Au2 . . 86.25(9) ?
N21 Au1 Au2 . . 97.32(9) ?
N11 Au1 Au2 . 2_665 96.43(9) ?
N21 Au1 Au2 . 2_665 85.98(8) ?
Au2 Au1 Au2 . 2_665 65.548(9) ?
Br2 Au2 Br1 . . 170.628(15) y
Br2 Au2 Au1 . . 87.120(12) ?
Br1 Au2 Au1 . . 98.067(12) ?
Br2 Au2 Au1 . 2_665 87.536(11) ?
Br1 Au2 Au1 . 2_665 97.312(11) ?
Au1 Au2 Au1 . 2_665 114.452(8) ?
C16 N11 C12 . . 109.8(3) ?
C16 N11 Au1 . . 113.2(2) ?
C12 N11 Au1 . . 113.4(2) ?
N11 C12 C13 . . 110.8(3) ?
C12 C13 C14 . . 112.3(3) ?
C15 C14 C13 . . 109.3(3) ?
C15 C14 C17 . . 111.5(3) ?
C13 C14 C17 . . 111.5(3) ?
C16 C15 C14 . . 112.4(3) ?
N11 C16 C15 . . 110.0(3) ?
C22 N21 C26 . . 109.5(3) ?
C22 N21 Au1 . . 111.9(2) ?
C26 N21 Au1 . . 114.0(2) ?
N21 C22 C23 . . 110.6(3) ?
C22 C23 C24 . . 112.6(3) ?
C27 C24 C23 . . 111.1(3) ?
C27 C24 C25 . . 110.8(3) ?
C23 C24 C25 . . 109.7(3) ?
C26 C25 C24 . . 112.4(3) ?
N21 C26 C25 . . 111.1(3) ?
C16 N11 H01 . . 108(3) ?
C12 N11 H01 . . 109(3) ?
Au1 N11 H01 . . 103(3) ?
N11 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
N11 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C12 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
C12 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.9 ?
C15 C14 H14 . . 108.2 ?
C13 C14 H14 . . 108.2 ?
C17 C14 H14 . . 108.2 ?
C16 C15 H15A . . 109.1 ?
C14 C15 H15A . . 109.1 ?
C16 C15 H15B . . 109.1 ?
C14 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.8 ?
N11 C16 H16A . . 109.7 ?
C15 C16 H16A . . 109.7 ?
N11 C16 H16B . . 109.7 ?
C15 C16 H16B . . 109.7 ?
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 . . 108(3) ?
C26 N21 H02 . . 107(3) ?
Au1 N21 H02 . . 106(3) ?
N21 C22 H22A . . 109.5 ?
C23 C22 H22A . . 109.5 ?
N21 C22 H22B . . 109.5 ?
C23 C22 H22B . . 109.5 ?
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 . . 107.8 ?
C27 C24 H24 . . 108.4 ?
C23 C24 H24 . . 108.4 ?
C25 C24 H24 . . 108.4 ?
C26 C25 H25A . . 109.1 ?
C24 C25 H25A . . 109.1 ?
C26 C25 H25B . . 109.1 ?
C24 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.9 ?
N21 C26 H26A . . 109.4 ?
C25 C26 H26A . . 109.4 ?
N21 C26 H26B . . 109.4 ?
C25 C26 H26B . . 109.4 ?
H26A C26 H26B . . 108.0 ?
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 N11 . 2.062(3) y
Au1 N21 . 2.064(3) y
Au1 Au2 . 3.2988(3) y
Au1 Au2 2_665 3.3094(2) y
Au2 Br2 . 2.4006(4) y
Au2 Br1 . 2.4027(4) y
N11 C16 . 1.485(5) ?
N11 C12 . 1.492(5) ?
C12 C13 . 1.511(5) ?
C13 C14 . 1.527(5) ?
C14 C15 . 1.527(5) ?
C14 C17 . 1.529(5) ?
C15 C16 . 1.518(5) ?
N21 C22 . 1.491(5) ?
N21 C26 . 1.496(5) ?
C22 C23 . 1.511(5) ?
C23 C24 . 1.526(6) ?
C24 C27 . 1.521(5) ?
C24 C25 . 1.528(5) ?
C25 C26 . 1.513(5) ?
N11 H01 . 0.90(3) ?
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 . 0.89(3) ?
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 Br2 2_665 0.90(3) 2.80(4) 3.457(3) 131(4) yes
N11 H01 Br1 . 0.90(3) 2.81(4) 3.518(3) 136(4) yes
N21 H02 Br1 2_665 0.89(3) 2.77(4) 3.487(3) 138(4) yes
N21 H02 Br2 . 0.89(3) 2.84(4) 3.462(3) 128(4) yes
C13 H13A Br2 1_545 0.99 3.19 3.867(4) 127.1 ?
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 . . . . 60.2(4) ?
Au1 N11 C12 C13 . . . . -67.5(3) y
N11 C12 C13 C14 . . . . -56.5(4) ?
C12 C13 C14 C15 . . . . 51.7(4) ?
C12 C13 C14 C17 . . . . 175.4(3) y
C13 C14 C15 C16 . . . . -52.4(4) ?
C17 C14 C15 C16 . . . . -176.1(3) y
C12 N11 C16 C15 . . . . -60.4(4) ?
Au1 N11 C16 C15 . . . . 67.4(3) y
C14 C15 C16 N11 . . . . 57.7(4) ?
C26 N21 C22 C23 . . . . -60.0(4) ?
Au1 N21 C22 C23 . . . . 67.3(3) y
N21 C22 C23 C24 . . . . 57.3(4) ?
C22 C23 C24 C27 . . . . -174.6(3) y
C22 C23 C24 C25 . . . . -51.7(4) ?
C27 C24 C25 C26 . . . . 174.0(3) y
C23 C24 C25 C26 . . . . 51.0(4) ?
C22 N21 C26 C25 . . . . 59.7(4) ?
Au1 N21 C26 C25 . . . . -66.5(3) y
C24 C25 C26 N21 . . . . -56.1(4) ?
