#------------------------------------------------------------------------------
#$Date: 2024-03-05 22:43:10 +0200 (Tue, 05 Mar 2024) $
#$Revision: 290331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023012.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_2023012
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] Cl'
_chemical_formula_moiety         'C12 H26 Au N2 +, Cl -'
_chemical_formula_sum            'C12 H26 Au Cl N2'
_chemical_formula_weight         430.76
_chemical_name_systematic
;
Bis(4-methylpiperidine-κN)gold(I) chloride
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 103.946(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4068(3)
_cell_length_b                   25.2542(15)
_cell_length_c                   9.3395(4)
_cell_measurement_reflns_used    8714
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9001
_cell_measurement_theta_min      2.2423
_cell_volume                     1466.58(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 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49187
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.387
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    10.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.128
_refine_diff_density_min         -1.569
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0326
_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)+(0.0141P)²+1.4591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0482
_reflns_number_gt                3650
_reflns_number_total             4248
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2046sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2023012--2023016.cif.'
_cod_original_cell_volume        1466.57(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2023012
_cod_database_fobs_code          2023012
_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   0.223
_shelx_estimated_absorpt_t_max   0.905
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.27850(2) 0.58105(2) 0.41086(2) 0.01228(4) Uani d 1 . .
Cl Cl1 0.07333(15) 0.42372(4) 0.25393(10) 0.01992(19) Uani d 1 . .
N N11 0.2215(5) 0.63222(12) 0.5676(3) 0.0128(6) Uani d 1 . .
H H01 0.139(6) 0.6124(15) 0.613(4) 0.018(11) Uiso d 1 . .
C C12 0.0986(6) 0.68027(15) 0.5052(4) 0.0161(8) Uani d 1 . .
H H12A 0.058954 0.700496 0.585531 0.019 Uiso calc 1 . .
H H12B -0.035734 0.669534 0.434086 0.019 Uiso calc 1 . .
C C13 0.2293(6) 0.71521(14) 0.4282(4) 0.0142(7) Uani d 1 . .
H H13A 0.145689 0.747515 0.391848 0.017 Uiso calc 1 . .
H H13B 0.255772 0.696126 0.341629 0.017 Uiso calc 1 . .
C C14 0.4460(6) 0.73133(13) 0.5300(4) 0.0132(7) Uani d 1 . .
H H14 0.415702 0.754449 0.609509 0.016 Uiso calc 1 . .
C C15 0.5635(6) 0.68186(14) 0.6033(4) 0.0140(7) Uani d 1 . .
H H15A 0.609429 0.660305 0.527799 0.017 Uiso calc 1 . .
H H15B 0.694185 0.692767 0.677764 0.017 Uiso calc 1 . .
C C16 0.4233(6) 0.64834(14) 0.6774(4) 0.0147(7) Uani d 1 . .
H H16A 0.503518 0.616358 0.720715 0.018 Uiso calc 1 . .
H H16B 0.385848 0.668775 0.758154 0.018 Uiso calc 1 . .
C C17 0.5835(7) 0.76300(15) 0.4479(4) 0.0220(8) Uani d 1 . .
H H17A 0.719934 0.772491 0.516224 0.033 Uiso calc 1 . .
H H17B 0.506738 0.795302 0.407423 0.033 Uiso calc 1 . .
H H17C 0.612007 0.741537 0.367261 0.033 Uiso calc 1 . .
N N21 0.3334(5) 0.52931(12) 0.2545(3) 0.0130(6) Uani d 1 . .
H H02 0.263(6) 0.4985(13) 0.266(4) 0.013(10) Uiso d 1 . .
C C22 0.5644(6) 0.51457(15) 0.2782(4) 0.0179(8) Uani d 1 . .
H H22A 0.580427 0.486931 0.206434 0.021 Uiso calc 1 . .
H H22B 0.617710 0.499995 0.378789 0.021 Uiso calc 1 . .
C C23 0.6963(6) 0.56314(14) 0.2590(4) 0.0153(7) Uani d 1 . .
H H23A 0.848096 0.552454 0.270366 0.018 Uiso calc 1 . .
H H23B 0.691474 0.589011 0.337743 0.018 Uiso calc 1 . .
C C24 0.6152(6) 0.58985(13) 0.1087(4) 0.0136(7) Uani d 1 . .
H H24 0.644492 0.565394 0.031584 0.016 Uiso calc 1 . .
C C25 0.3730(6) 0.59872(14) 0.0763(4) 0.0135(7) Uani d 1 . .
H H25A 0.342750 0.627499 0.140439 0.016 Uiso calc 1 . .
H H25B 0.320515 0.610250 -0.027422 0.016 Uiso calc 1 . .
C C26 0.2515(6) 0.54938(14) 0.1015(4) 0.0152(7) Uani d 1 . .
H H26A 0.096396 0.557673 0.084466 0.018 Uiso calc 1 . .
H H26B 0.268389 0.521627 0.030228 0.018 Uiso calc 1 . .
C C27 0.7347(7) 0.64190(15) 0.0996(5) 0.0230(9) Uani d 1 . .
H H27A 0.692865 0.655692 -0.001365 0.035 Uiso calc 1 . .
H H27B 0.890107 0.635485 0.126803 0.035 Uiso calc 1 . .
H H27C 0.697421 0.667793 0.167558 0.035 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
N11 Au1 N21 . . 179.43(12) y
C12 N11 C16 . . 109.5(3) ?
C12 N11 Au1 . . 113.8(2) ?
C16 N11 Au1 . . 112.8(2) ?
N11 C12 C13 . . 111.2(3) ?
C12 C13 C14 . . 112.4(3) ?
C17 C14 C15 . . 111.8(3) ?
C17 C14 C13 . . 111.9(3) ?
C15 C14 C13 . . 109.5(3) ?
C16 C15 C14 . . 112.2(3) ?
N11 C16 C15 . . 110.3(3) ?
C26 N21 C22 . . 109.6(3) ?
C26 N21 Au1 . . 112.7(2) ?
C22 N21 Au1 . . 112.8(2) ?
N21 C22 C23 . . 109.9(3) ?
C22 C23 C24 . . 112.8(3) ?
C25 C24 C23 . . 110.5(3) ?
C25 C24 C27 . . 111.2(3) ?
C23 C24 C27 . . 111.4(3) ?
C26 C25 C24 . . 112.6(3) ?
N21 C26 C25 . . 110.7(3) ?
C12 N11 H01 . . 109(3) ?
C16 N11 H01 . . 109(3) ?
Au1 N11 H01 . . 102(3) ?
N11 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
N11 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
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 ?
C17 C14 H14 . . 107.8 ?
C15 C14 H14 . . 107.8 ?
C13 C14 H14 . . 107.8 ?
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 . . 109.6 ?
C15 C16 H16A . . 109.6 ?
N11 C16 H16B . . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
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 ?
C26 N21 H02 . . 109(2) ?
C22 N21 H02 . . 106(3) ?
Au1 N21 H02 . . 106(3) ?
N21 C22 H22A . . 109.7 ?
C23 C22 H22A . . 109.7 ?
N21 C22 H22B . . 109.7 ?
C23 C22 H22B . . 109.7 ?
H22A C22 H22B . . 108.2 ?
C22 C23 H23A . . 109.0 ?
C24 C23 H23A . . 109.0 ?
C22 C23 H23B . . 109.0 ?
C24 C23 H23B . . 109.0 ?
H23A C23 H23B . . 107.8 ?
C25 C24 H24 . . 107.9 ?
C23 C24 H24 . . 107.9 ?
C27 C24 H24 . . 107.9 ?
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 . . 109.5 ?
C25 C26 H26A . . 109.5 ?
N21 C26 H26B . . 109.5 ?
C25 C26 H26B . . 109.5 ?
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 N11 . 2.051(3) y
Au1 N21 . 2.052(3) y
N11 C12 . 1.487(5) ?
N11 C16 . 1.499(5) ?
C12 C13 . 1.513(5) ?
C13 C14 . 1.536(5) ?
C14 C17 . 1.526(5) ?
C14 C15 . 1.532(5) ?
C15 C16 . 1.517(5) ?
N21 C26 . 1.488(4) ?
N21 C22 . 1.490(5) ?
C22 C23 . 1.524(5) ?
C23 C24 . 1.531(5) ?
C24 C25 . 1.524(5) ?
C24 C27 . 1.534(5) ?
C25 C26 . 1.517(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 . 0.92(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
N21 H02 Cl1 . 0.92(3) 2.23(3) 3.144(3) 171(3) yes
N11 H01 Cl1 3_566 0.90(3) 2.25(3) 3.140(3) 170(4) yes
C16 H16A Cl1 3_666 0.99 2.85 3.623(4) 135.5 yes
C22 H22B Au1 3_666 0.99 2.80 3.724(4) 154.9 yes
C23 H23A Au1 1_655 0.99 2.85 3.685(4) 142.9 yes
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 . . . . 60.1(4) ?
Au1 N11 C12 C13 . . . . -67.1(3) y
N11 C12 C13 C14 . . . . -56.3(4) ?
C12 C13 C14 C17 . . . . 175.6(3) y
C12 C13 C14 C15 . . . . 51.1(4) ?
C17 C14 C15 C16 . . . . -176.5(3) y
C13 C14 C15 C16 . . . . -52.0(4) ?
C12 N11 C16 C15 . . . . -60.6(4) ?
Au1 N11 C16 C15 . . . . 67.2(3) y
C14 C15 C16 N11 . . . . 57.6(4) ?
C26 N21 C22 C23 . . . . 61.4(4) ?
Au1 N21 C22 C23 . . . . -65.0(3) y
N21 C22 C23 C24 . . . . -56.1(4) ?
C22 C23 C24 C25 . . . . 49.5(4) ?
C22 C23 C24 C27 . . . . 173.6(3) y
C23 C24 C25 C26 . . . . -49.2(4) ?
C27 C24 C25 C26 . . . . -173.4(3) y
C22 N21 C26 C25 . . . . -61.6(4) ?
Au1 N21 C26 C25 . . . . 64.9(3) y
C24 C25 C26 N21 . . . . 56.0(4) ?
