Catalytic domino amination and oxidative coupling of gold acetylides and isolation of key vinylene digold intermediates as a new class of ditopic N-heterocyclic carbene complexes
Zhang, Jun; Chen, Haifeng; Wang, Jiwei; Hu, Zejun; Xu, Sheng; Shi, Min; Chem. Commun.  (2017) –; doi:10.1039/C7CC06069F

data_7120642
_publ_section_title
;
 Catalytic domino amination and oxidative coupling of gold acetylides and
 isolation of key vinylene digold intermediates as a new class of ditopic
 N-heterocyclic carbene complexes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06069F
_journal_year                    2017
_chemical_formula_moiety         'C64 H65 Au2 N2 O P2, C F3 O3 S, C H2 Cl2'
_chemical_formula_sum            'C66 H67 Au2 Cl2 F3 N2 O4 P2 S'
_chemical_formula_weight         1568.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-11-02 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.0470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1480(12)
_cell_length_b                   18.4838(12)
_cell_length_c                   19.8362(14)
_cell_measurement_reflns_used    9790
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.544
_cell_measurement_theta_min      2.39
_cell_volume                     6326.6(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0222
_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       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45853
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.999
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.614
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.858
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0692 before and 0.0350 after correction.
The Ratio of minimum to maximum transmission is 0.7759.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       block
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         3.320
_refine_diff_density_min         -1.888
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     747
_refine_ls_number_reflns         12444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0251
_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/[\s^2^(Fo^2^)+(0.0192P)^2^+21.1044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10868
_reflns_number_total             12444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06069f2.cif
_cod_data_source_block           mo_dm16665_0m
_cod_database_code               7120642
_shelx_estimated_absorpt_t_max   0.443
_shelx_estimated_absorpt_t_min   0.324
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C23(H23), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C66(H66A,H66B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C30(H30),
 C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39),
  C40(H40), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48),
 C49(H49), C50(H50), C51(H51), C52(H52), C54(H54), C55(H55), C56(H56), C57(H57),
  C58(H58), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'