#------------------------------------------------------------------------------
#$Date: 2019-11-23 04:29:17 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232121 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/70/4347028.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_4347028
loop_
_publ_author_name
'Hu, Ji-Yun'
'Zhang, Jing'
'Wang, Gao-Xiang'
'Sun, Hao-Ling'
'Zhang, Jun-Long'
_publ_section_title
;
 Constructing a Catalytic Cycle for C-F to C-X (X = O, S, N) Bond
 Transformation Based on Gold-Mediated Ligand Nucleophilic Attack.
;
_journal_issue                   5
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2274
_journal_page_last               2283
_journal_paper_doi               10.1021/acs.inorgchem.5b02634
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C16.5 H26 Au0.5 Cl2 Ga0.5 O0.75 P'
_chemical_formula_weight         471.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.1617(17)
_cell_length_b                   15.9205(12)
_cell_length_c                   11.9664(9)
_cell_measurement_temperature    296(2)
_cell_volume                     4222.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0391
_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       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24850
_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         26.039
_diffrn_reflns_theta_min         1.838
_exptl_absorpt_coefficient_mu    4.462
_exptl_absorpt_correction_T_max  0.640
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             1880
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0398
_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)+(0.0750P)²+3.0976P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3254
_reflns_number_total             4319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b02634_si_004.cif
_cod_data_source_block           6
_cod_original_formula_sum        'C16.50 H26 Au0.50 Cl2 Ga0.50 O0.75 P'
_cod_database_code               4347028
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
C1 C 0.5091(3) 0.3250(3) 0.7319(5) 0.0386(13) Uani 1 1 d . . .
C2 C 0.4709(3) 0.3942(4) 0.7399(5) 0.0415(13) Uani 1 1 d . . .
C3 C 0.4968(3) 0.4684(4) 0.7741(6) 0.0585(18) Uani 1 1 d . . .
H3A H 0.4732 0.5166 0.7782 0.070 Uiso 1 1 calc R U .
C4 C 0.5570(4) 0.4729(5) 0.8022(6) 0.071(2) Uani 1 1 d . . .
H4A H 0.5731 0.5237 0.8265 0.085 Uiso 1 1 calc R U .
C5 C 0.5925(3) 0.4051(5) 0.7952(6) 0.0613(19) Uani 1 1 d . . .
H5A H 0.6330 0.4092 0.8149 0.074 Uiso 1 1 calc R U .
C6 C 0.5696(3) 0.3291(4) 0.7590(6) 0.0466(14) Uani 1 1 d . . .
C7 C 0.6086(4) 0.2500 0.7410(8) 0.053(2) Uani 1 2 d S T P
C8 C 0.6648(5) 0.2500 0.8177(11) 0.084(4) Uani 1 2 d S T P
H8A H 0.6522 0.2500 0.8945 0.126 Uiso 1 2 calc R U P
H8B H 0.6885 0.2992 0.8032 0.126 Uiso 0.5 1 calc R U P
H8C H 0.6885 0.2008 0.8032 0.126 Uiso 0.5 1 calc R U P
C9 C 0.6295(5) 0.2500 0.6161(10) 0.078(3) Uani 1 2 d S T P
H9A H 0.5948 0.2500 0.5681 0.118 Uiso 1 2 calc R U P
H9B H 0.6533 0.2008 0.6018 0.118 Uiso 0.5 1 calc R U P
H9C H 0.6533 0.2992 0.6018 0.118 Uiso 0.5 1 calc R U P
C10 C 0.3493(4) 0.4404(5) 0.8301(8) 0.072(2) Uani 1 1 d . . .
C11 C 0.2843(4) 0.4091(7) 0.8265(9) 0.114(4) Uani 1 1 d . . .
H11A H 0.2624 0.4321 0.8885 0.172 Uiso 1 1 calc R U .
H11B H 0.2839 0.3489 0.8309 0.172 Uiso 1 1 calc R U .
H11C H 0.2658 0.4266 0.7578 0.172 Uiso 1 1 calc R U .
C12 C 0.3494(5) 0.5360(6) 0.8353(10) 0.113(4) Uani 1 1 d . . .
H12A H 0.3283 0.5542 0.9010 0.170 Uiso 1 1 calc R U .
H12B H 0.3298 0.5582 0.7701 0.170 Uiso 1 1 calc R U .
H12C H 0.3903 0.5560 0.8379 0.170 Uiso 1 1 calc R U .
C13 C 0.3777(4) 0.4019(8) 0.9341(7) 0.109(4) Uani 1 1 d . . .
H13A H 0.3588 0.4248 0.9995 0.164 Uiso 1 1 calc R U .
H13B H 0.4201 0.4146 0.9355 0.164 Uiso 1 1 calc R U .
H13C H 0.3722 0.3421 0.9329 0.164 Uiso 1 1 calc R U .
C14 C 0.3818(4) 0.4462(4) 0.5711(6) 0.065(2) Uani 1 1 d . . .
C15 C 0.4122(4) 0.3886(5) 0.4882(6) 0.080(2) Uani 1 1 d . . .
H15A H 0.4099 0.4128 0.4148 0.120 Uiso 1 1 calc R U .
H15B H 0.3924 0.3350 0.4883 0.120 Uiso 1 1 calc R U .
H15C H 0.4538 0.3814 0.5087 0.120 Uiso 1 1 calc R U .
C16 C 0.3152(4) 0.4533(6) 0.5416(8) 0.105(3) Uani 1 1 d . . .
H16A H 0.3110 0.4812 0.4709 0.158 Uiso 1 1 calc R U .
H16B H 0.2947 0.4850 0.5983 0.158 Uiso 1 1 calc R U .
H16C H 0.2979 0.3981 0.5368 0.158 Uiso 1 1 calc R U .
C17 C 0.4126(5) 0.5318(5) 0.5637(8) 0.097(3) Uani 1 1 d . . .
H17A H 0.4063 0.5550 0.4906 0.145 Uiso 1 1 calc R U .
H17B H 0.4550 0.5253 0.5770 0.145 Uiso 1 1 calc R U .
H17C H 0.3957 0.5688 0.6188 0.145 Uiso 1 1 calc R U .
O1 O 0.4862(2) 0.2500 0.6903(4) 0.0374(12) Uani 1 2 d S T P
Cl1 Cl 0.6785(3) 0.2500 0.3392(5) 0.166(2) Uani 1 2 d S T P
Cl2 Cl 0.7426(2) 0.2500 0.0728(3) 0.1045(12) Uani 1 2 d S T P
Cl3 Cl 0.81073(18) 0.3642(3) 0.2847(3) 0.1548(16) Uani 1 1 d . . .
P1 P 0.38958(8) 0.39130(10) 0.70862(14) 0.0418(4) Uani 1 1 d . . .
Ga1 Ga 0.76190(6) 0.2500 0.24789(11) 0.0698(3) Uani 1 2 d S T P
Au1 Au 0.36785(2) 0.2500 0.69907(3) 0.04291(14) Uani 1 2 d S T P
O2 O 0.4900(10) 0.6644(11) 0.857(2) 0.069(6) Uani 0.25 1 d . . P
C19 C 0.4733(10) 0.7114(11) 0.9261(16) 0.104(6) Uani 0.5 1 d . . P
H19A H 0.4954 0.6957 0.9928 0.125 Uiso 0.5 1 calc R U P
H19B H 0.4317 0.6957 0.9400 0.125 Uiso 0.5 1 calc R U P
C18 C 0.4992(10) 0.7087(12) 0.7878(18) 0.099(7) Uani 0.5 1 d . . P
H18A H 0.4711 0.6931 0.7293 0.119 Uiso 0.5 1 calc R U P
H18B H 0.5389 0.6931 0.7604 0.119 Uiso 0.5 1 calc R U P
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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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'
Ga Ga 0.2307 1.6083 '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
_geom_angle_site_symmetry_3
C6 C1 O1 118.6(5) . .
C6 C1 C2 122.4(5) . .
O1 C1 C2 118.9(5) . .
C3 C2 C1 116.5(6) . .
C3 C2 P1 119.3(5) . .
C1 C2 P1 124.1(4) . .
C2 C3 C4 121.4(7) . .
C5 C4 C3 120.8(7) . .
C4 C5 C6 120.6(6) . .
C1 C6 C5 118.2(6) . .
C1 C6 C7 118.2(6) . .
C5 C6 C7 123.5(6) . .
C6 C7 C6 109.4(7) . 7_565
C6 C7 C8 111.6(5) . .
C6 C7 C8 111.6(5) 7_565 .
C6 C7 C9 107.4(5) . .
C6 C7 C9 107.4(5) 7_565 .
C8 C7 C9 109.1(9) . .
C13 C10 C11 106.4(9) . .
C13 C10 C12 111.5(8) . .
C11 C10 C12 109.2(8) . .
C13 C10 P1 105.6(6) . .
C11 C10 P1 107.0(6) . .
C12 C10 P1 116.5(7) . .
C15 C14 C16 109.0(7) . .
C15 C14 C17 107.7(7) . .
C16 C14 C17 110.7(7) . .
C15 C14 P1 104.6(5) . .
C16 C14 P1 109.2(6) . .
C17 C14 P1 115.3(6) . .
C1 O1 C1 118.5(6) . 7_565
C2 P1 C14 104.9(3) . .
C2 P1 C10 107.3(3) . .
C14 P1 C10 116.3(4) . .
C2 P1 Au1 103.82(19) . .
C14 P1 Au1 113.2(2) . .
C10 P1 Au1 110.2(3) . .
Cl2 Ga1 Cl1 109.1(2) . .
Cl2 Ga1 Cl3 107.44(11) . .
Cl1 Ga1 Cl3 109.10(15) . .
Cl2 Ga1 Cl3 107.44(11) . 7_565
Cl1 Ga1 Cl3 109.10(15) . 7_565
Cl3 Ga1 Cl3 114.6(3) . 7_565
P1 Au1 P1 155.18(8) 7_565 .
C18 O2 C19 100.3(19) . .
O2 C19 C19 129.5(14) . 7_575
O2 C19 C18 38.4(12) . .
C19 C19 C18 91.4(9) 7_575 .
O2 C18 C18 129.7(15) . 7_575
O2 C18 C19 41.3(13) . .
C18 C18 C19 88.6(9) 7_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.381(8) .
C1 O1 1.389(6) .
C1 C2 1.392(8) .
C2 C3 1.377(8) .
C2 P1 1.841(6) .
C3 C4 1.377(10) .
C4 C5 1.339(11) .
C5 C6 1.383(9) .
C6 C7 1.543(8) .
C7 C6 1.543(8) 7_565
C7 C8 1.547(13) .
C7 C9 1.565(15) .
C10 C13 1.524(13) .
C10 C11 1.524(12) .
C10 C12 1.525(13) .
C10 P1 1.876(8) .
C14 C15 1.511(10) .
C14 C16 1.521(11) .
C14 C17 1.526(10) .
C14 P1 1.871(7) .
O1 C1 1.390(6) 7_565
Cl1 Ga1 2.147(4) .
Cl2 Ga1 2.138(3) .
Cl3 Ga1 2.161(3) .
P1 Au1 2.3033(15) .
Ga1 Cl3 2.161(3) 7_565
Au1 P1 2.3033(15) 7_565
O2 C18 1.11(3) .
O2 C19 1.18(2) .
C19 C19 1.23(3) 7_575
C19 C18 1.75(3) .
C18 C18 1.31(4) 7_575
