Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes
Yazdani, Sima; Junor, Glen P.; Peltier, Jesse L.; Gembicky, Milan; Jazzar, Rodolphe; Grotjahn, Douglas B.; Bertrand, Guy; ACS Catalysis  (2020) 5190–; doi:10.1021/acscatal.0c01352

data_4517585
_publ_section_title
;
 Influence of Carbene and Phosphine Ligands on the Catalytic Activity of
 Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5190
_journal_paper_doi               10.1021/acscatal.0c01352
_journal_year                    2020
_chemical_formula_moiety         'C44 H66 Au N2, B F4, 2(C6 H6)'
_chemical_formula_sum            'C56 H78 Au B F4 N2'
_chemical_formula_weight         1062.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.402(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9392(11)
_cell_length_b                   18.2892(10)
_cell_length_c                   17.3878(10)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.23
_cell_volume                     5018.1(5)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44280
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         1.704
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.985
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0451 before and 0.0417 after correction. The Ratio of minimum to maximum transmission is 0.9612. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         10265
_refine_ls_number_restraints     278
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0188
_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/[\s^2^(Fo^2^)+(0.0178P)^2^+3.5773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0427
_refine_ls_wR_factor_ref         0.0476
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7867
_reflns_number_total             10265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            '[(L6)2Au][BF4].cif'
_cod_data_source_block           '[(l6)2au][bf4]'
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4517585
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.716
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.48(2)
 0.52(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 F1-B1 \\sim F3-B1 \\sim F2-B1 \\sim F4-B1
 with sigma of 0.02
 F4-B2 \\sim F2-B2 \\sim F1-B2 \\sim F6-B2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C2A) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(N2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C26) = Uanis(C27A)
Uanis(C6) = Uanis(C6A)
Uanis(C4A) = Uanis(C4)
Uanis(C8) = Uanis(C8A)
Uanis(F5) = Uanis(F4)
Uanis(B1) = Uanis(B2)
Uanis(C7A) = Uanis(C3)
5. Rigid body (RIGU) restrains
 F1, F2, F3, F4, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F5, F6, B2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C23, C24A, C25A, C26A, C27A, C28A, C29A, C31
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C2A, C3A, C4A, C5, C6A, C7A, C9A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C24, C25, C26, C27, C28, C30, C31
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C2, C3, C4, C5, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C2)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C6)=Sof(H6A)=
 Sof(H6B)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(H9C)=1-FVAR(1)
 Sof(C2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C6A)=
 Sof(H6AA)=Sof(H6AB)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=FVAR(1)
 Sof(C24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=1-FVAR(2)
 Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=
 Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=
 Sof(H29E)=Sof(H29F)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=FVAR(2)
 Sof(F3)=Sof(F4)=Sof(B1)=1-FVAR(3)
 Sof(F5)=Sof(F6)=Sof(B2)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C7(H7), C7A(H7A), C17(H17), C20(H20), C25(H25), C25A(H25A), C39(H39), C42(H42)
7.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3A(H3AA,H3AB), C4(H4A,H4B), C4A(H4AA,H4AB), C6(H6A,H6B),
 C6A(H6AA,H6AB), C26(H26A,H26B), C26A(H26C,H26D), C27(H27A,H27B), C27A(H27C,
 H27D), C28(H28A,H28B), C28A(H28C,H28D)
7.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C35(H35), C36(H36), C37(H37), C2S(H2S),
 C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S), C1S(H1S), C12S(H12S), C7S(H7S),
 C8S(H8S), C9S(H9S), C10S(H10S), C11S(H11S)
7.d Fitted hexagon refined as free rotating group:
 C2S(C3S,C4S,C5S,C6S,C1S), C12S(C7S,C8S,C9S,C10S,C11S)
7.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC),
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F),
 C30(H30A,H30B,H30C), C30A(H30D,H30E,H30F), C32(H32A,H32B,H32C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              20609
_shelx_hkl_checksum              40171
_olex2_submission_special_instructions 'No special instructions were received'