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_4127324
_publ_section_title
;
 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         'C12 H16 Au Cl2 N2 O, B F4, C2 H3 N'
_chemical_formula_sum            'C15 H19 Au B Cl2 F4 N2 O'
_chemical_formula_weight         598.00
_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             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_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                   7.4334(5)
_cell_length_b                   8.6838(6)
_cell_length_c                   30.722(2)
_cell_measurement_reflns_used    9365
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.44
_cell_volume                     1983.1(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            12099
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.676
_diffrn_reflns_theta_min         2.652
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.730
_exptl_absorpt_correction_T_max  0.8333
_exptl_absorpt_correction_T_min  0.4145
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0836 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.4974.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.309
_refine_diff_density_min         -1.763
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details
;
 Flack x determined using 1871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0194P)^2^+11.2301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                4708
_reflns_number_total             5070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09108_si_005.cif
_cod_data_source_block           eo02-76-outrjx
_cod_database_code               4127324
_shelx_estimated_absorpt_t_max   0.768
_shelx_estimated_absorpt_t_min   0.219
_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:
 C00L(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00F,H00G)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00H(H00H), C00K(H00L)
2.d Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00D), C00I(H00I,H00J,H00K), C4(H4A,H4B,H4C), C00P(H00N,H00O,
 H00P)
;
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'