#------------------------------------------------------------------------------
#$Date: 2019-11-25 15:45:31 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241239 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/08/4130881.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_4130881
loop_
_publ_author_name
'Kumar, Roopender'
'Linden, Anthony'
'Nevado, Cristina'
_publ_section_title
;
 Evidence for Direct Transmetalation of AuIII-F with Boronic
 Acids.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13790
_journal_page_last               13793
_journal_paper_doi               10.1021/jacs.6b07763
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C15 H16 Au F2 N O3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C15.5 H17 Au Cl F2 N O3'
_chemical_formula_weight         535.72
_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                 101.2087(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7561(2)
_cell_length_b                   16.1000(8)
_cell_length_c                   14.8396(2)
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      29.3690
_cell_measurement_theta_min      2.2310
_cell_volume                     3223.88(17)
_computing_cell_refinement
'CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)'
_computing_data_collection
'CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)'
_computing_data_reduction
'CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2014 and PLATON (Spek, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 'Atlas CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8280
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.419
_diffrn_reflns_theta_min         2.239
_exptl_absorpt_coefficient_mu    9.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.37.35g (Agilent Technologies, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_description       prism
_exptl_crystal_F_000             2040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         3.055
_refine_diff_density_min         -2.998
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0206P)²+42.4267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3745
_reflns_number_total             4068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b07763_si_005.cif
_cod_data_source_block           nv1508
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_hydrogens' value 'geom & difmap' was
changed to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        3223.86(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4130881
_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.
;
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
Au1 Au 0.63902(2) 0.58046(2) 0.66935(2) 0.03677(8) Uani 1 1 d . . .
F1 F 0.7816(3) 0.6050(2) 0.7281(3) 0.0509(9) Uani 1 1 d . . .
F2 F 0.6291(3) 0.6988(2) 0.6446(3) 0.0637(11) Uani 1 1 d . . .
N1 N 0.6538(3) 0.4598(2) 0.6926(3) 0.0313(9) Uani 1 1 d . . .
O1 O 0.4379(4) 0.6797(3) 0.5666(3) 0.0573(13) Uani 1 1 d . . .
O2 O 0.2583(4) 0.6151(3) 0.4978(4) 0.0664(15) Uani 1 1 d . . .
O3 O 0.2242(3) 0.4501(3) 0.5031(4) 0.0594(13) Uani 1 1 d . . .
C1 C 0.7414(4) 0.4306(3) 0.7354(4) 0.0371(12) Uani 1 1 d . . .
H1 H 0.7945 0.4678 0.7565 0.045 Uiso 1 1 calc R U .
C2 C 0.7550(4) 0.3465(3) 0.7490(4) 0.0407(13) Uani 1 1 d . . .
H2 H 0.8165 0.3251 0.7807 0.049 Uiso 1 1 calc R U .
C3 C 0.6774(4) 0.2942(3) 0.7156(4) 0.0387(12) Uani 1 1 d . . .
H3 H 0.6862 0.2360 0.7247 0.046 Uiso 1 1 calc R U .
C4 C 0.5860(4) 0.3239(3) 0.6686(4) 0.0310(10) Uani 1 1 d . . .
C5 C 0.5743(4) 0.4101(3) 0.6592(4) 0.0303(10) Uani 1 1 d . . .
C6 C 0.5075(4) 0.2617(3) 0.6301(4) 0.0379(12) Uani 1 1 d . . .
H61 H 0.4503 0.2686 0.6598 0.057 Uiso 1 1 calc R U .
H62 H 0.5342 0.2054 0.6415 0.057 Uiso 1 1 calc R U .
H63 H 0.4868 0.2705 0.5638 0.057 Uiso 1 1 calc R U .
C7 C 0.4866(4) 0.4587(3) 0.6174(4) 0.0316(11) Uani 1 1 d . . .
C8 C 0.5021(4) 0.5451(3) 0.6148(4) 0.0361(12) Uani 1 1 d . . .
C9 C 0.4237(5) 0.5965(3) 0.5754(4) 0.0438(14) Uani 1 1 d . . .
C10 C 0.3312(5) 0.5630(4) 0.5400(4) 0.0458(15) Uani 1 1 d . . .
C11 C 0.3161(4) 0.4770(4) 0.5420(4) 0.0423(13) Uani 1 1 d . . .
C12 C 0.3933(4) 0.4252(3) 0.5809(4) 0.0369(12) Uani 1 1 d . . .
H12 H 0.3829 0.3669 0.5829 0.044 Uiso 1 1 calc R U .
C13 C 0.4010(10) 0.7299(5) 0.6320(7) 0.111(4) Uani 1 1 d . . .
H131 H 0.3301 0.7402 0.6102 0.166 Uiso 1 1 calc R U .
H132 H 0.4366 0.7830 0.6394 0.166 Uiso 1 1 calc R U .
H133 H 0.4111 0.7010 0.6912 0.166 Uiso 1 1 calc R U .
C14 C 0.1710(7) 0.6185(7) 0.5375(6) 0.087(3) Uani 1 1 d . . .
H141 H 0.1225 0.5778 0.5070 0.131 Uiso 1 1 calc R U .
H142 H 0.1423 0.6743 0.5295 0.131 Uiso 1 1 calc R U .
H143 H 0.1888 0.6055 0.6032 0.131 Uiso 1 1 calc R U .
C15 C 0.2054(5) 0.3628(5) 0.4973(6) 0.067(2) Uani 1 1 d . . .
H151 H 0.2504 0.3364 0.4622 0.100 Uiso 1 1 calc R U .
H152 H 0.1367 0.3530 0.4665 0.100 Uiso 1 1 calc R U .
H153 H 0.2163 0.3391 0.5593 0.100 Uiso 1 1 calc R U .
Cl1 Cl 1.0032(2) 0.4798(2) 0.6532(3) 0.1440(17) Uani 1 1 d . . .
C16 C 1.0000 0.5384(6) 0.7500 0.064(3) Uani 1 2 d S T P
H161 H 1.0592 0.5746 0.7623 0.077 Uiso 1 1 d R U .
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'
Au Au -2.0133 8.8022 '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'
F F 0.0171 0.0103 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-15 14 1 0.0407 -14.9904 14.0066 1.0148 -0.2047 0.7386 0.6334
19 0 0 0.0950 18.9960 -0.0084 -0.0341 0.3866 -0.9196 -0.0295
15 -7 9 0.0954 15.0059 -7.0075 8.9690 -0.1157 -0.9890 -0.2250
-6 -7 20 0.1001 -5.9755 -6.9994 19.9948 -0.9723 -0.2698 -0.0725
2 -22 -5 0.0982 1.9851 -22.0005 -4.9809 0.0165 -0.0241 -0.9992
7 10 -18 0.0925 6.9790 9.9988 -18.0011 0.9445 0.1759 0.2212
-15 -13 -3 0.0672 -15.0055 -12.9932 -2.9596 -0.3178 0.7702 -0.5657
14 14 3 0.0770 14.0061 13.9936 2.9606 0.3074 -0.7189 0.6101
0 -1 -21 0.0974 -0.0275 -0.9979 -20.9767 0.8095 0.5646 -0.2714
0 4 20 0.0763 0.0273 3.9980 19.9754 -0.7405 -0.5290 0.3889
14 -15 -2 0.1053 13.9890 -15.0060 -2.0111 0.2134 -0.6661 -0.6856
1 22 5 0.0743 1.0143 21.9992 4.9755 0.0445 -0.1211 0.9945
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
F2 Au1 N1 177.81(18) .
F2 Au1 C8 100.3(2) .
N1 Au1 C8 81.17(19) .
F2 Au1 F1 85.18(17) .
N1 Au1 F1 93.38(16) .
C8 Au1 F1 174.55(17) .
C1 N1 C5 123.4(4) .
C1 N1 Au1 118.8(4) .
C5 N1 Au1 117.7(3) .
C9 O1 C13 114.4(5) .
C10 O2 C14 115.6(5) .
C11 O3 C15 118.9(5) .
N1 C1 C2 120.0(5) .
N1 C1 H1 120.0 .
C2 C1 H1 120.0 .
C3 C2 C1 118.5(5) .
C3 C2 H2 120.8 .
C1 C2 H2 120.8 .
C2 C3 C4 122.0(5) .
C2 C3 H3 119.0 .
C4 C3 H3 119.0 .
C3 C4 C5 117.6(5) .
C3 C4 C6 118.2(4) .
C5 C4 C6 124.2(5) .
N1 C5 C4 118.4(5) .
N1 C5 C7 111.9(4) .
C4 C5 C7 129.7(5) .
C4 C6 H61 109.5 .
C4 C6 H62 109.5 .
H61 C6 H62 109.5 .
C4 C6 H63 109.5 .
H61 C6 H63 109.5 .
H62 C6 H63 109.5 .
C12 C7 C8 120.1(5) .
C12 C7 C5 124.9(4) .
C8 C7 C5 115.0(5) .
C9 C8 C7 119.3(6) .
C9 C8 Au1 126.7(4) .
C7 C8 Au1 114.1(4) .
O1 C9 C10 118.9(5) .
O1 C9 C8 120.6(6) .
C10 C9 C8 120.4(5) .
O2 C10 C9 118.2(6) .
O2 C10 C11 121.3(7) .
C9 C10 C11 120.3(5) .
O3 C11 C12 124.2(6) .
O3 C11 C10 115.9(5) .
C12 C11 C10 119.9(6) .
C11 C12 C7 120.0(5) .
C11 C12 H12 120.0 .
C7 C12 H12 120.0 .
O1 C13 H131 109.5 .
O1 C13 H132 109.5 .
H131 C13 H132 109.5 .
O1 C13 H133 109.5 .
H131 C13 H133 109.5 .
H132 C13 H133 109.5 .
O2 C14 H141 109.5 .
O2 C14 H142 109.5 .
H141 C14 H142 109.5 .
O2 C14 H143 109.5 .
H141 C14 H143 109.5 .
H142 C14 H143 109.5 .
O3 C15 H151 109.5 .
O3 C15 H152 109.5 .
H151 C15 H152 109.5 .
O3 C15 H153 109.5 .
H151 C15 H153 109.5 .
H152 C15 H153 109.5 .
Cl1 C16 Cl1 113.8(7) 2_756
Cl1 C16 H161 108.8 2_756
Cl1 C16 H161 108.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 F2 1.940(3) .
Au1 N1 1.977(4) .
Au1 C8 1.984(6) .
Au1 F1 2.025(4) .
N1 C1 1.334(7) .
N1 C5 1.368(6) .
O1 C9 1.365(7) .
O1 C13 1.430(9) .
O2 C10 1.363(7) .
O2 C14 1.438(10) .
O3 C11 1.354(8) .
O3 C15 1.428(10) .
C1 C2 1.376(7) .
C1 H1 0.9500 .
C2 C3 1.374(8) .
C2 H2 0.9500 .
C3 C4 1.398(7) .
C3 H3 0.9500 .
C4 C5 1.401(6) .
C4 C6 1.502(7) .
C5 C7 1.470(7) .
C6 H61 0.9800 .
C6 H62 0.9800 .
C6 H63 0.9800 .
C7 C12 1.401(8) .
C7 C8 1.409(7) .
C8 C9 1.394(8) .
C9 C10 1.387(10) .
C10 C11 1.402(9) .
C11 C12 1.385(7) .
C12 H12 0.9500 .
C13 H131 0.9800 .
C13 H132 0.9800 .
C13 H133 0.9800 .
C14 H141 0.9800 .
C14 H142 0.9800 .
C14 H143 0.9800 .
C15 H151 0.9800 .
C15 H152 0.9800 .
C15 H153 0.9800 .
Cl1 C16 1.726(6) .
C16 Cl1 1.726(6) 2_756
C16 H161 0.9900 .
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
C5 N1 C1 C2 -0.9(9)
Au1 N1 C1 C2 -177.2(4)
N1 C1 C2 C3 1.6(9)
C1 C2 C3 C4 0.0(9)
C2 C3 C4 C5 -2.2(9)
C2 C3 C4 C6 176.6(6)
C1 N1 C5 C4 -1.3(8)
Au1 N1 C5 C4 175.0(4)
C1 N1 C5 C7 178.6(5)
Au1 N1 C5 C7 -5.1(6)
C3 C4 C5 N1 2.8(8)
C6 C4 C5 N1 -176.0(5)
C3 C4 C5 C7 -177.1(5)
C6 C4 C5 C7 4.1(9)
N1 C5 C7 C12 -177.2(5)
C4 C5 C7 C12 2.7(9)
N1 C5 C7 C8 3.5(7)
C4 C5 C7 C8 -176.6(5)
C12 C7 C8 C9 -0.2(8)
C5 C7 C8 C9 179.2(5)
C12 C7 C8 Au1 -179.8(4)
C5 C7 C8 Au1 -0.4(6)
C13 O1 C9 C10 79.5(9)
C13 O1 C9 C8 -103.8(8)
C7 C8 C9 O1 -175.8(5)
Au1 C8 C9 O1 3.7(8)
C7 C8 C9 C10 0.8(8)
Au1 C8 C9 C10 -179.7(4)
C14 O2 C10 C9 -120.5(8)
C14 O2 C10 C11 64.3(9)
O1 C9 C10 O2 0.1(9)
C8 C9 C10 O2 -176.5(5)
O1 C9 C10 C11 175.4(6)
C8 C9 C10 C11 -1.3(9)
C15 O3 C11 C12 -3.1(9)
C15 O3 C11 C10 176.0(6)
O2 C10 C11 O3 -2.8(9)
C9 C10 C11 O3 -177.9(5)
O2 C10 C11 C12 176.3(5)
C9 C10 C11 C12 1.2(9)
O3 C11 C12 C7 178.3(5)
C10 C11 C12 C7 -0.7(9)
C8 C7 C12 C11 0.2(8)
C5 C7 C12 C11 -179.1(5)
