Mechanism of Au(III)-Mediated Alkoxycyclization of a 1,6-Enyne.
Reiersølmoen, Ann Christin; Csókás, Dániel; Pápai, Imre; Fiksdahl, Anne; Erdélyi, Máté; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b09108

data_4127328
_publ_section_title
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 Mechanism of Au(III)-Mediated Alkoxycyclization of a 1,6-Enyne.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b09108
_journal_year                    2019
_chemical_formula_moiety         'C14 H16 Au Br2 F3 N2 O3'
_chemical_formula_sum            'C14 H16 Au Br2 F3 N2 O3'
_chemical_formula_weight         674.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.585(3)
_cell_length_b                   8.843(3)
_cell_length_c                   28.858(11)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      31.53
_cell_measurement_theta_min      2.40
_cell_volume                     1935.6(12)
_computing_cell_refinement       'SAINT V8.38A (Sheldrick, 2016)'
_computing_data_reduction        'SAINT V8.38A (Sheldrick, 2016)'
_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      101.11
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            21650
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.583
_diffrn_reflns_theta_min         2.702
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    23.531
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1308 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.6354.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    4.420
_exptl_crystal_description       plate
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.775
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details
;
 Flack x determined using 2388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0141P)^2^+0.2398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0502
_refine_ls_wR_factor_ref         0.0513
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5923
_reflns_number_total             6418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09108_si_004.cif
_cod_data_source_block           acr_11_22_100k_0m_a
_cod_depositor_comments
;

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         337.04
_cod_original_formula_moiety         '0.5(C14 H16 Au Br2 F3 N2 O3)'
_cod_original_formula_units_Z            8
_cod_original_cell_volume        1935.7(13)
_cod_original_formula_sum        'C7 H8 Au0.50 Br F1.50 N O1.50'
_cod_database_code               4127328
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.539
_shelx_estimated_absorpt_t_min   0.105
_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:
 C0D(H0D)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              75137
_shelx_hkl_checksum              83820
_olex2_submission_special_instructions 'No special instructions were received'