#------------------------------------------------------------------------------
#$Date: 2019-11-23 04:29:34 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232122 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/70/4347029.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_4347029
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            'C34 H48 Au Cl F2.5 N0.5 O2 P2'
_chemical_formula_weight         837.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 117.926(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0778(4)
_cell_length_b                   26.4908(7)
_cell_length_c                   12.2698(5)
_cell_measurement_reflns_used    11230
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      28.2290
_cell_measurement_theta_min      3.5770
_cell_volume                     3468.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22702
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.376
_diffrn_reflns_theta_min         2.975
_exptl_absorpt_coefficient_mu    4.454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         7498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0261
_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)+(0.0224P)²+5.0247P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6619
_reflns_number_total             7498
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b02634_si_003.cif
_cod_data_source_block           1
_cod_original_cell_volume        3468.6(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C34 H48 Au Cl F2.50 N0.50 O2 P2'
_cod_database_code               4347029
_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.
;
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.69170(2) 0.15454(2) 0.35711(2) 0.01930(5) Uani 1 1 d . . . . .
P1 P 0.90586(8) 0.16027(3) 0.48671(7) 0.01828(17) Uani 1 1 d . . . . .
P2 P 0.55076(7) 0.15009(3) 0.14779(7) 0.01806(17) Uani 1 1 d . . . . .
C1 C 0.9965(3) 0.14746(12) 0.4042(3) 0.0185(6) Uani 1 1 d . . . . .
C2 C 1.1249(3) 0.15849(13) 0.4563(3) 0.0260(7) Uani 1 1 d . . . . .
H2A H 1.1646 0.1735 0.5338 0.031 Uiso 1 1 calc R U . . .
C3 C 1.1942(3) 0.14774(13) 0.3958(3) 0.0277(8) Uani 1 1 d . . . . .
H3A H 1.2788 0.1560 0.4320 0.033 Uiso 1 1 calc R U . . .
C4 C 1.1381(3) 0.12487(13) 0.2824(3) 0.0253(7) Uani 1 1 d . . . . .
H4A H 1.1852 0.1177 0.2422 0.030 Uiso 1 1 calc R U . . .
C5 C 1.0114(3) 0.11230(12) 0.2266(3) 0.0191(6) Uani 1 1 d . . . . .
C6 C 0.9431(3) 0.12465(11) 0.2884(3) 0.0161(6) Uani 1 1 d . . . . .
C7 C 0.9406(3) 0.08441(13) 0.1045(3) 0.0219(7) Uani 1 1 d . . . . .
C8 C 0.8144(3) 0.11097(12) 0.0366(3) 0.0205(7) Uani 1 1 d . . . . .
C9 C 0.7544(3) 0.12270(13) -0.0881(3) 0.0262(7) Uani 1 1 d . . . . .
H9A H 0.7937 0.1159 -0.1360 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6366(4) 0.14440(15) -0.1415(3) 0.0319(8) Uani 1 1 d . . . . .
H10A H 0.5978 0.1528 -0.2247 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5764(3) 0.15357(13) -0.0717(3) 0.0267(8) Uani 1 1 d . . . . .
H11A H 0.4961 0.1672 -0.1100 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6325(3) 0.14302(12) 0.0552(3) 0.0197(7) Uani 1 1 d . . . . .
C13 C 0.7533(3) 0.12269(12) 0.1057(3) 0.0170(6) Uani 1 1 d . . . . .
C14 C 0.9184(3) 0.02944(13) 0.1314(3) 0.0304(8) Uani 1 1 d . . . . .
H14A H 0.8738 0.0115 0.0551 0.046 Uiso 1 1 calc R U . . .
H14B H 0.8701 0.0294 0.1752 0.046 Uiso 1 1 calc R U . . .
H14C H 0.9976 0.0133 0.1808 0.046 Uiso 1 1 calc R U . . .
C15 C 1.0125(3) 0.08306(15) 0.0302(3) 0.0320(8) Uani 1 1 d . . . . .
H15A H 1.0267 0.1169 0.0117 0.048 Uiso 1 1 calc R U . . .
H15B H 0.9645 0.0649 -0.0453 0.048 Uiso 1 1 calc R U . . .
H15C H 1.0915 0.0665 0.0774 0.048 Uiso 1 1 calc R U . . .
C16 C 0.9490(3) 0.22569(14) 0.5532(3) 0.0283(8) Uani 1 1 d . . . . .
C17 C 1.0727(4) 0.23172(17) 0.6726(4) 0.0454(11) Uani 1 1 d . . . . .
H17A H 1.0843 0.2665 0.6971 0.068 Uiso 1 1 calc R U . . .
H17B H 1.1410 0.2208 0.6588 0.068 Uiso 1 1 calc R U . . .
H17C H 1.0704 0.2116 0.7365 0.068 Uiso 1 1 calc R U . . .
C18 C 0.8416(4) 0.24272(15) 0.5796(4) 0.0382(9) Uani 1 1 d . . . . .
H18A H 0.8586 0.2761 0.6139 0.057 Uiso 1 1 calc R U . . .
H18B H 0.8353 0.2199 0.6371 0.057 Uiso 1 1 calc R U . . .
H18C H 0.7641 0.2428 0.5041 0.057 Uiso 1 1 calc R U . . .
C19 C 0.9485(4) 0.25941(14) 0.4526(4) 0.0401(9) Uani 1 1 d . . . . .
H19A H 0.9701 0.2933 0.4832 0.060 Uiso 1 1 calc R U . . .
H19B H 0.8665 0.2592 0.3825 0.060 Uiso 1 1 calc R U . . .
H19C H 1.0085 0.2470 0.4285 0.060 Uiso 1 1 calc R U . . .
C20 C 0.9605(3) 0.10872(14) 0.6059(3) 0.0310(8) Uani 1 1 d . . . . .
C21 C 1.1024(4) 0.10197(18) 0.6790(4) 0.0516(12) Uani 1 1 d . . . . .
H21A H 1.1212 0.0751 0.7377 0.077 Uiso 1 1 calc R U . . .
H21B H 1.1399 0.1327 0.7218 0.077 Uiso 1 1 calc R U . . .
H21C H 1.1354 0.0938 0.6236 0.077 Uiso 1 1 calc R U . . .
C22 C 0.9046(5) 0.11789(19) 0.6938(4) 0.0487(11) Uani 1 1 d . . . . .
H22A H 0.9319 0.0918 0.7551 0.073 Uiso 1 1 calc R U . . .
H22B H 0.8148 0.1176 0.6478 0.073 Uiso 1 1 calc R U . . .
H22C H 0.9321 0.1501 0.7333 0.073 Uiso 1 1 calc R U . . .
C23 C 0.9040(4) 0.06050(14) 0.5324(4) 0.0381(9) Uani 1 1 d . . . . .
H23A H 0.9276 0.0322 0.5877 0.057 Uiso 1 1 calc R U . . .
H23B H 0.9346 0.0556 0.4737 0.057 Uiso 1 1 calc R U . . .
H23C H 0.8144 0.0634 0.4897 0.057 Uiso 1 1 calc R U . . .
C24 C 0.4505(3) 0.20867(13) 0.0942(3) 0.0263(7) Uani 1 1 d . . . . .
C25 C 0.5338(4) 0.25043(14) 0.0863(3) 0.0343(8) Uani 1 1 d . . . . .
H25A H 0.4865 0.2811 0.0589 0.051 Uiso 1 1 calc R U . . .
H25B H 0.5631 0.2407 0.0288 0.051 Uiso 1 1 calc R U . . .
H25C H 0.6042 0.2556 0.1661 0.051 Uiso 1 1 calc R U . . .
C26 C 0.3287(3) 0.20584(16) -0.0275(4) 0.0413(10) Uani 1 1 d . . . . .
H26A H 0.2869 0.2379 -0.0442 0.062 Uiso 1 1 calc R U . . .
H26B H 0.2753 0.1804 -0.0216 0.062 Uiso 1 1 calc R U . . .
H26C H 0.3475 0.1975 -0.0932 0.062 Uiso 1 1 calc R U . . .
C27 C 0.4173(4) 0.22263(16) 0.1972(4) 0.0383(9) Uani 1 1 d . . . . .
H27A H 0.3659 0.2523 0.1738 0.057 Uiso 1 1 calc R U . . .
H27B H 0.4929 0.2290 0.2722 0.057 Uiso 1 1 calc R U . . .
H27C H 0.3726 0.1952 0.2098 0.057 Uiso 1 1 calc R U . . .
C28 C 0.4576(3) 0.08969(13) 0.1088(3) 0.0258(7) Uani 1 1 d . . . . .
C29 C 0.5527(3) 0.04793(14) 0.1782(4) 0.0334(8) Uani 1 1 d . . . . .
H29A H 0.5105 0.0160 0.1619 0.050 Uiso 1 1 calc R U . . .
H29B H 0.5920 0.0547 0.2651 0.050 Uiso 1 1 calc R U . . .
H29C H 0.6153 0.0470 0.1509 0.050 Uiso 1 1 calc R U . . .
C30 C 0.3623(3) 0.09232(16) 0.1578(4) 0.0401(10) Uani 1 1 d . . . . .
H30A H 0.3148 0.0616 0.1381 0.060 Uiso 1 1 calc R U . . .
H30B H 0.3068 0.1203 0.1205 0.060 Uiso 1 1 calc R U . . .
H30C H 0.4056 0.0967 0.2457 0.060 Uiso 1 1 calc R U . . .
C31 C 0.3911(4) 0.07669(16) -0.0292(4) 0.0423(10) Uani 1 1 d . . . . .
H31A H 0.3457 0.0456 -0.0418 0.063 Uiso 1 1 calc R U . . .
H31B H 0.4521 0.0730 -0.0580 0.063 Uiso 1 1 calc R U . . .
H31C H 0.3339 0.1033 -0.0742 0.063 Uiso 1 1 calc R U . . .
C32 C 0.6268(5) -0.00611(18) 0.5755(5) 0.0588(13) Uani 1 1 d . . . . .
C33 C 0.5538(5) 0.01879(16) 0.6154(4) 0.0468(11) Uani 1 1 d . . . . .
C34 C 0.4289(5) 0.02501(18) 0.5444(5) 0.0584(13) Uani 1 1 d . . . . .
F1 F 0.7493(3) -0.01275(13) 0.6521(3) 0.0849(10) Uani 1 1 d . . . . .
F2 F 0.6093(3) 0.03617(11) 0.7317(3) 0.0792(9) Uani 1 1 d . . . . .
F3 F 0.3546(5) 0.04944(16) 0.5856(5) 0.0905(14) Uani 0.5 1 d . . P A 1
O1 O 0.81666(18) 0.11245(8) 0.23146(18) 0.0170(4) Uani 1 1 d . . . . .
O2 O 0.4024(7) 0.0874(3) 0.6624(7) 0.079(2) Uani 0.5 1 d . . P A 2
O3 O 0.2498(9) 0.0349(3) 0.5524(13) 0.133(5) Uani 0.5 1 d . . P A 2
N1 N 0.3546(5) 0.04944(16) 0.5856(5) 0.0905(14) Uani 0.5 1 d . . P A 2
Cl1 Cl 0.56901(9) 0.12665(3) 0.47836(8) 0.0336(2) Uani 1 1 d . . . . .
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'
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'
P P 0.1023 0.0942 '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'
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_3
P1 Au1 P2 139.81(3) .
P1 Au1 Cl1 111.74(3) .
P2 Au1 Cl1 107.05(3) .
C1 P1 C20 102.21(15) .
C1 P1 C16 107.07(15) .
C20 P1 C16 113.98(16) .
C1 P1 Au1 111.78(10) .
C20 P1 Au1 110.97(12) .
C16 P1 Au1 110.52(11) .
C12 P2 C28 100.78(15) .
C12 P2 C24 108.21(15) .
C28 P2 C24 113.61(16) .
C12 P2 Au1 111.21(10) .
C28 P2 Au1 111.36(11) .
C24 P2 Au1 111.19(11) .
C6 C1 C2 116.1(3) .
C6 C1 P1 122.1(2) .
C2 C1 P1 121.8(2) .
C3 C2 C1 122.0(3) .
C4 C3 C2 120.0(3) .
C3 C4 C5 120.8(3) .
C4 C5 C6 118.0(3) .
C4 C5 C7 125.5(3) .
C6 C5 C7 116.4(3) .
O1 C6 C1 119.2(3) .
O1 C6 C5 117.6(3) .
C1 C6 C5 123.1(3) .
C5 C7 C8 105.7(2) .
C5 C7 C15 112.6(3) .
C8 C7 C15 112.8(3) .
C5 C7 C14 108.7(3) .
C8 C7 C14 108.9(3) .
C15 C7 C14 108.1(3) .
C9 C8 C13 118.0(3) .
C9 C8 C7 125.3(3) .
C13 C8 C7 116.6(3) .
C10 C9 C8 120.4(3) .
C11 C10 C9 120.2(3) .
C10 C11 C12 122.2(3) .
C13 C12 C11 115.3(3) .
C13 C12 P2 121.3(2) .
C11 C12 P2 123.2(3) .
O1 C13 C8 117.3(3) .
O1 C13 C12 118.9(3) .
C8 C13 C12 123.7(3) .
C19 C16 C17 110.2(3) .
C19 C16 C18 108.3(3) .
C17 C16 C18 108.0(3) .
C19 C16 P1 107.1(2) .
C17 C16 P1 117.3(3) .
C18 C16 P1 105.7(2) .
C23 C20 C21 108.5(3) .
C23 C20 C22 108.9(3) .
C21 C20 C22 110.3(3) .
C23 C20 P1 104.6(2) .
C21 C20 P1 115.5(3) .
C22 C20 P1 108.8(3) .
C25 C24 C26 109.5(3) .
C25 C24 C27 108.1(3) .
C26 C24 C27 108.2(3) .
C25 C24 P2 106.4(2) .
C26 C24 P2 117.8(3) .
C27 C24 P2 106.4(2) .
C30 C28 C29 108.7(3) .
C30 C28 C31 110.0(3) .
C29 C28 C31 108.6(3) .
C30 C28 P2 109.4(3) .
C29 C28 P2 105.6(2) .
C31 C28 P2 114.3(3) .
F1 C32 C33 119.9(5) .
F1 C32 C34 121.4(5) 3_656
C33 C32 C34 118.7(5) 3_656
F2 C33 C34 119.6(5) .
F2 C33 C32 117.6(5) .
C34 C33 C32 122.8(5) .
C33 C34 F3 122.8(5) .
C33 C34 C32 118.5(5) 3_656
F3 C34 C32 118.7(5) 3_656
C6 O1 C13 114.6(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 P1 2.3215(8) .
Au1 P2 2.3266(8) .
Au1 Cl1 2.6495(8) .
P1 C1 1.837(3) .
P1 C20 1.880(3) .
P1 C16 1.882(4) .
P2 C12 1.830(3) .
P2 C28 1.884(3) .
P2 C24 1.887(3) .
C1 C6 1.394(4) .
C1 C2 1.403(5) .
C2 C3 1.385(5) .
C3 C4 1.371(5) .
C4 C5 1.392(4) .
C5 C6 1.396(4) .
C5 C7 1.524(4) .
C6 O1 1.388(3) .
C7 C8 1.524(5) .
C7 C15 1.526(4) .
C7 C14 1.544(5) .
C8 C9 1.387(4) .
C8 C13 1.394(4) .
C9 C10 1.382(5) .
C10 C11 1.379(5) .
C11 C12 1.406(5) .
C12 C13 1.399(4) .
C13 O1 1.390(3) .
C16 C19 1.522(5) .
C16 C17 1.534(5) .
C16 C18 1.544(5) .
C20 C23 1.527(5) .
C20 C21 1.528(5) .
C20 C22 1.537(5) .
C24 C25 1.529(5) .
C24 C26 1.530(5) .
C24 C27 1.539(5) .
C28 C30 1.530(5) .
C28 C29 1.533(5) .
C28 C31 1.536(5) .
C32 F1 1.342(6) .
C32 C33 1.362(7) .
C32 C34 1.393(7) 3_656
C33 F2 1.342(5) .
C33 C34 1.353(7) .
C34 F3 1.380(6) .
C34 C32 1.393(7) 3_656
