#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:20:15 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/66/4036670.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4036670
loop_
_publ_author_name
'Mir, Roya'
'Dudding, Travis'
_publ_section_title
;
 A Au(I)-Precatalyst with a Cyclopropenium Counterion: An Unusual Ion
 Pair.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2675
_journal_page_last               2679
_journal_paper_doi               10.1021/acs.joc.6b00241
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C16 H8 Au N2 O4, C15 H29 N2'
_chemical_formula_sum            'C31 H37 Au N4 O4'
_chemical_formula_weight         726.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.1382(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7379(5)
_cell_length_b                   9.4418(3)
_cell_length_c                   18.8452(6)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.73
_cell_measurement_theta_min      2.39
_cell_volume                     3031.78(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            42033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.171
_diffrn_reflns_theta_min         2.250
_exptl_absorpt_coefficient_mu    4.893
_exptl_absorpt_correction_T_max  0.4046
_exptl_absorpt_correction_T_min  0.1321
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.126
_refine_diff_density_max         1.502
_refine_diff_density_min         -1.202
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0303
_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)+(0.0376P)²+8.1360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4379
_reflns_number_total             5803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00241_si_001.cif
_cod_data_source_block           RM08729b_0m_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036670
_shelx_shelxl_version_number     2014/7
_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   0.215
_shelx_estimated_absorpt_t_max   0.578
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.2500 0.7500 0.0000 0.03187(5) Uani 1 2 d S . P . .
O1 O 0.31076(19) 0.4966(4) 0.1267(2) 0.0802(10) Uani 1 1 d . . . . .
O2 O 0.11167(15) 0.8173(3) 0.07988(16) 0.0550(7) Uani 1 1 d . . . . .
N1 N 0.21775(13) 0.6712(2) 0.08581(13) 0.0309(4) Uani 1 1 d . . . . .
C1 C 0.25342(18) 0.5622(3) 0.13162(19) 0.0422(7) Uani 1 1 d . . . . .
C2 C 0.21023(16) 0.5412(3) 0.18822(16) 0.0356(6) Uani 1 1 d . . . . .
C3 C 0.15045(15) 0.6382(3) 0.17409(14) 0.0297(5) Uani 1 1 d . . . . .
C4 C 0.15506(16) 0.7220(3) 0.10820(16) 0.0298(5) Uani 1 1 d . . . . .
C5 C 0.1007(2) 0.6485(4) 0.2184(2) 0.0479(8) Uani 1 1 d . . . . .
H5 H 0.062(4) 0.716(6) 0.208(3) 0.081(18) Uiso 1 1 d . . . . .
C6 C 0.1132(3) 0.5559(5) 0.2781(2) 0.0587(10) Uani 1 1 d . . . . .
H6 H 0.083(3) 0.555(5) 0.309(2) 0.066(13) Uiso 1 1 d . . . . .
C7 C 0.1727(3) 0.4575(5) 0.2916(2) 0.0632(11) Uani 1 1 d . . . . .
H7 H 0.180(3) 0.398(5) 0.329(3) 0.069(13) Uiso 1 1 d . . . . .
C8 C 0.2223(2) 0.4475(4) 0.2467(2) 0.0576(10) Uani 1 1 d . . . . .
H8 H 0.265(3) 0.377(5) 0.252(3) 0.078(15) Uiso 1 1 d . . . . .
C1A C 0.0385(3) 1.0721(5) -0.0044(3) 0.0257(9) Uani 0.5 1 d . . P A -1
C3A C -0.0019(3) 0.9593(5) -0.0461(3) 0.0268(9) Uani 0.5 1 d . . P A -1
C2A C 0.0591(3) 1.0223(6) -0.0645(3) 0.0302(10) Uani 0.5 1 d . . P A -1
H2A H 0.0923 1.0277 -0.0963 0.036 Uiso 0.5 1 calc R U P A -1
N1A N 0.0505(2) 1.1609(3) 0.0506(2) 0.0350(7) Uani 0.5 1 d G . P A -1
N2A N -0.0574(2) 0.8654(3) -0.0603(2) 0.0350(7) Uani 0.5 1 d G . P A -1
C4A C 0.1186(2) 1.2590(3) 0.0604(3) 0.0516(18) Uani 0.5 1 d G . P A -1
H4A H 0.1259 1.3090 0.1087 0.062 Uiso 0.5 1 calc R U P A -1
C5A C 0.1928(2) 1.1814(4) 0.0637(3) 0.062(2) Uani 0.5 1 d G . P A -1
H5C H 0.2002 1.1053 0.1004 0.094 Uiso 0.5 1 calc R U P A -1
H5B H 0.2372 1.2472 0.0778 0.094 Uiso 0.5 1 calc R U P A -1
H5A H 0.1897 1.1408 0.0151 0.094 Uiso 0.5 1 calc R U P A -1
C6A C 0.0993(3) 1.3710(3) -0.0007(3) 0.090(3) Uani 0.5 1 d G . P A -1
H6C H 0.0809 1.3243 -0.0489 0.135 Uiso 0.5 1 calc R U P A -1
H6B H 0.1465 1.4265 0.0011 0.135 Uiso 0.5 1 calc R U P A -1
H6A H 0.0581 1.4340 0.0066 0.135 Uiso 0.5 1 calc R U P A -1
C7A C 0.0074(2) 1.1585(4) 0.1063(2) 0.078(3) Uani 0.5 1 d G . P A -1
H7A H -0.0327 1.0814 0.0926 0.093 Uiso 0.5 1 calc R U P A -1
C8A C -0.0360(3) 1.2970(4) 0.1066(3) 0.099(2) Uani 0.5 1 d G . P A -1
H8C H -0.0452 1.3431 0.0583 0.149 Uiso 0.5 1 calc R U P A -1
H8B H -0.0043 1.3593 0.1451 0.149 Uiso 0.5 1 calc R U P A -1
H8A H -0.0864 1.2780 0.1166 0.149 Uiso 0.5 1 calc R U P A -1
C9A C 0.0619(3) 1.1229(4) 0.1815(2) 0.102(4) Uani 0.5 1 d G . P A -1
H9C H 0.1093 1.0771 0.1753 0.153 Uiso 0.5 1 calc R U P A -1
H9B H 0.0353 1.0586 0.2074 0.153 Uiso 0.5 1 calc R U P A -1
H9A H 0.0765 1.2101 0.2102 0.153 Uiso 0.5 1 calc R U P A -1
C10A C -0.1092(2) 0.8367(3) -0.0123(2) 0.0524(18) Uani 0.5 1 d G . P A -1
H10A H -0.0932 0.9011 0.0314 0.063 Uiso 0.5 1 calc R U P A -1
C11A C -0.1955(2) 0.8754(4) -0.0568(3) 0.062(2) Uani 0.5 1 d G . P A -1
H11C H -0.1971 0.9730 -0.0748 0.094 Uiso 0.5 1 calc R U P A -1
H11B H -0.2300 0.8665 -0.0244 0.094 Uiso 0.5 1 calc R U P A -1
H11A H -0.2133 0.8107 -0.0988 0.094 Uiso 0.5 1 calc R U P A -1
C12A C -0.1035(3) 0.6866(3) 0.0153(3) 0.090(3) Uani 0.5 1 d G . P A -1
H12C H -0.1473 0.6312 -0.0153 0.135 Uiso 0.5 1 calc R U P A -1
H12B H -0.1059 0.6857 0.0667 0.135 Uiso 0.5 1 calc R U P A -1
H12A H -0.0538 0.6451 0.0126 0.135 Uiso 0.5 1 calc R U P A -1
C13A C -0.0615(3) 0.7689(4) -0.1253(3) 0.071(3) Uani 0.5 1 d G . P A -1
H13A H -0.0997 0.6916 -0.1243 0.085 Uiso 0.5 1 calc R U P A -1
C14A C -0.0906(3) 0.8450(5) -0.1980(2) 0.102(4) Uani 0.5 1 d G . P A -1
H14C H -0.1392 0.8957 -0.1993 0.153 Uiso 0.5 1 calc R U P A -1
H14B H -0.1009 0.7761 -0.2384 0.153 Uiso 0.5 1 calc R U P A -1
H14A H -0.0508 0.9127 -0.2035 0.153 Uiso 0.5 1 calc R U P A -1
C15A C 0.0185(3) 0.7005(4) -0.1165(3) 0.099(2) Uani 0.5 1 d G . P A -1
H15C H 0.0591 0.7740 -0.1068 0.149 Uiso 0.5 1 calc R U P A -1
H15B H 0.0182 0.6500 -0.1620 0.149 Uiso 0.5 1 calc R U P A -1
H15A H 0.0295 0.6336 -0.0752 0.149 Uiso 0.5 1 calc R U P A -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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
N1 Au1 N1 180.0 7_565
C1 N1 C4 109.6(2) .
C1 N1 Au1 126.77(19) .
C4 N1 Au1 123.58(18) .
O1 C1 N1 125.5(3) .
O1 C1 C2 126.5(3) .
N1 C1 C2 108.1(2) .
C3 C2 C8 121.5(3) .
C3 C2 C1 107.2(2) .
C8 C2 C1 131.3(3) .
C2 C3 C5 121.4(3) .
C2 C3 C4 107.3(2) .
C5 C3 C4 131.2(3) .
O2 C4 N1 126.3(3) .
O2 C4 C3 125.9(3) .
N1 C4 C3 107.8(2) .
C3 C5 C6 117.4(4) .
C3 C5 H5 119(4) .
C6 C5 H5 124(4) .
C7 C6 C5 121.1(4) .
C7 C6 H6 116(3) .
C5 C6 H6 123(3) .
C6 C7 C8 121.2(3) .
C6 C7 H7 121(3) .
C8 C7 H7 118(3) .
C7 C8 C2 117.4(4) .
C7 C8 H8 126(3) .
C2 C8 H8 117(3) .
N1A C1A C2A 149.0(5) .
N1A C1A C3A 151.9(5) .
C2A C1A C3A 59.0(4) .
N2A C3A C2A 149.0(5) .
N2A C3A C1A 151.5(5) .
C2A C3A C1A 59.4(4) .
C3A C2A C1A 61.5(4) .
C3A C2A H2A 149.2 .
C1A C2A H2A 149.2 .
C1A N1A C7A 123.9(2) .
C1A N1A C4A 116.5(3) .
C7A N1A C4A 119.2 .
C3A N2A C10A 124.2(3) .
C3A N2A C13A 116.3(3) .
C10A N2A C13A 119.1 .
N1A C4A C5A 112.0 .
N1A C4A C6A 109.4 .
C5A C4A C6A 112.4 .
N1A C4A H4A 107.6 .
C5A C4A H4A 107.6 .
C6A C4A H4A 107.6 .
C4A C5A H5C 109.5 .
C4A C5A H5B 109.5 .
H5C C5A H5B 109.5 .
C4A C5A H5A 109.5 .
H5C C5A H5A 109.5 .
H5B C5A H5A 109.5 .
C4A C6A H6C 109.5 .
C4A C6A H6B 109.5 .
H6C C6A H6B 109.5 .
C4A C6A H6A 109.5 .
H6C C6A H6A 109.5 .
H6B C6A H6A 109.5 .
N1A C7A C9A 110.4 .
N1A C7A C8A 110.9 .
C9A C7A C8A 112.3 .
N1A C7A H7A 107.6 .
C9A C7A H7A 107.6 .
C8A C7A H7A 107.6 .
C7A C8A H8C 109.5 .
C7A C8A H8B 109.5 .
H8C C8A H8B 109.5 .
C7A C8A H8A 109.5 .
H8C C8A H8A 109.5 .
H8B C8A H8A 109.5 .
C7A C9A H9C 109.5 .
C7A C9A H9B 109.5 .
H9C C9A H9B 109.5 .
C7A C9A H9A 109.5 .
H9C C9A H9A 109.5 .
H9B C9A H9A 109.5 .
N2A C10A C12A 113.0 .
N2A C10A C11A 108.1 .
C12A C10A C11A 111.4 .
N2A C10A H10A 108.1 .
C12A C10A H10A 108.1 .
C11A C10A H10A 108.1 .
C10A C11A H11C 109.5 .
C10A C11A H11B 109.5 .
H11C C11A H11B 109.5 .
C10A C11A H11A 109.5 .
H11C C11A H11A 109.5 .
H11B C11A H11A 109.5 .
C10A C12A H12C 109.5 .
C10A C12A H12B 109.5 .
H12C C12A H12B 109.5 .
C10A C12A H12A 109.5 .
H12C C12A H12A 109.5 .
H12B C12A H12A 109.5 .
C14A C13A N2A 112.1 .
C14A C13A C15A 112.0 .
N2A C13A C15A 109.5 .
C14A C13A H13A 107.7 .
N2A C13A H13A 107.7 .
C15A C13A H13A 107.7 .
C13A C14A H14C 109.5 .
C13A C14A H14B 109.5 .
H14C C14A H14B 109.5 .
C13A C14A H14A 109.5 .
H14C C14A H14A 109.5 .
H14B C14A H14A 109.5 .
C13A C15A H15C 109.5 .
C13A C15A H15B 109.5 .
H15C C15A H15B 109.5 .
C13A C15A H15A 109.5 .
H15C C15A H15A 109.5 .
H15B C15A H15A 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 N1 2.002(2) 7_565
Au1 N1 2.003(2) .
O1 C1 1.217(4) .
O2 C4 1.208(3) .
N1 C1 1.379(4) .
N1 C4 1.380(3) .
C1 C2 1.489(5) .
C2 C3 1.370(4) .
C2 C8 1.383(4) .
C3 C5 1.378(4) .
C3 C4 1.493(4) .
C5 C6 1.393(5) .
C5 H5 0.92(6) .
C6 C7 1.374(6) .
C6 H6 0.90(4) .
C7 C8 1.384(6) .
C7 H7 0.89(5) .
C8 H8 0.99(5) .
C1A N1A 1.304(6) .
C1A C2A 1.368(7) .
C1A C3A 1.397(7) .
C3A N2A 1.297(6) .
C3A C2A 1.362(7) .
C2A H2A 0.9500 .
N1A C7A 1.4603 .
N1A C4A 1.4916 .
N2A C10A 1.4816 .
N2A C13A 1.5124 .
C4A C5A 1.4927 .
C4A C6A 1.5309 .
C4A H4A 1.0000 .
C5A H5C 0.9800 .
C5A H5B 0.9800 .
C5A H5A 0.9800 .
C6A H6C 0.9800 .
C6A H6B 0.9800 .
C6A H6A 0.9800 .
C7A C9A 1.5142 .
C7A C8A 1.5181 .
C7A H7A 1.0000 .
C8A H8C 0.9800 .
C8A H8B 0.9800 .
C8A H8A 0.9800 .
C9A H9C 0.9800 .
C9A H9B 0.9800 .
C9A H9A 0.9800 .
C10A C12A 1.5036 .
C10A C11A 1.5705 .
C10A H10A 1.0000 .
C11A H11C 0.9800 .
C11A H11B 0.9800 .
C11A H11A 0.9800 .
C12A H12C 0.9800 .
C12A H12B 0.9800 .
C12A H12A 0.9800 .
C13A C14A 1.5045 .
C13A C15A 1.5253 .
C13A H13A 1.0000 .
C14A H14C 0.9800 .
C14A H14B 0.9800 .
C14A H14A 0.9800 .
C15A H15C 0.9800 .
C15A H15B 0.9800 .
C15A H15A 0.9800 .
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
C4 N1 C1 O1 -179.3(4)
Au1 N1 C1 O1 0.0(5)
C4 N1 C1 C2 -0.1(3)
Au1 N1 C1 C2 179.19(18)
O1 C1 C2 C3 179.2(4)
N1 C1 C2 C3 0.0(3)
O1 C1 C2 C8 -0.2(6)
N1 C1 C2 C8 -179.4(3)
C8 C2 C3 C5 1.3(5)
C1 C2 C3 C5 -178.2(3)
C8 C2 C3 C4 179.5(3)
C1 C2 C3 C4 0.0(3)
C1 N1 C4 O2 179.9(3)
Au1 N1 C4 O2 0.6(5)
C1 N1 C4 C3 0.1(3)
Au1 N1 C4 C3 -179.20(17)
C2 C3 C4 O2 -179.9(3)
C5 C3 C4 O2 -1.9(6)
C2 C3 C4 N1 -0.1(3)
C5 C3 C4 N1 177.9(3)
C2 C3 C5 C6 -0.3(5)
C4 C3 C5 C6 -178.0(3)
C3 C5 C6 C7 -0.5(6)
C5 C6 C7 C8 0.3(7)
C6 C7 C8 C2 0.6(6)
C3 C2 C8 C7 -1.4(5)
C1 C2 C8 C7 177.9(4)
N1A C1A C3A N2A 3.3(16)
C2A C1A C3A N2A -177.5(10)
N1A C1A C3A C2A -179.2(10)
N2A C3A C2A C1A 177.6(9)
N1A C1A C2A C3A 179.3(9)
C2A C1A N1A C7A -175.6(7)
C3A C1A N1A C7A 3.1(11)
C2A C1A N1A C4A -2.4(10)
C3A C1A N1A C4A 176.3(8)
C2A C3A N2A C10A 176.1(7)
C1A C3A N2A C10A -8.2(11)
C2A C3A N2A C13A 3.8(10)
C1A C3A N2A C13A 179.5(8)
C1A N1A C4A C5A -52.9(3)
C7A N1A C4A C5A 120.6
C1A N1A C4A C6A 72.4(3)
C7A N1A C4A C6A -114.1
C1A N1A C7A C9A 114.9(3)
C4A N1A C7A C9A -58.0
C1A N1A C7A C8A -119.9(3)
C4A N1A C7A C8A 67.2
C3A N2A C10A C12A -119.9(3)
C13A N2A C10A C12A 52.2
C3A N2A C10A C11A 116.4(3)
C13A N2A C10A C11A -71.5
C3A N2A C13A C14A -72.1(3)
C10A N2A C13A C14A 115.2
C3A N2A C13A C15A 52.9(3)
C10A N2A C13A C15A -119.9
