Gold(I)-Catalyzed Cyclization/Carbonylation Cascade Reaction of 1,6-Diynes: An Access to β,γ-Unsaturated Ketones.
Bao, Ming; Lu, Wei; Cai, Yanping; Qiu, Lihua; Xu, Xinfang; The Journal of organic chemistry 82 (2017) 13386–13395; doi:10.1021/acs.joc.7b02461

data_4033256
_publ_section_title
;
 Gold(I)-Catalyzed Cyclization/Carbonylation Cascade Reaction of
 1,6-Diynes: An Access to \b,\g-Unsaturated Ketones.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13386
_journal_page_last               13395
_journal_paper_doi               10.1021/acs.joc.7b02461
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C27 H25 Br N2 O4 S'
_chemical_formula_sum            'C27 H25 Br N2 O4 S'
_chemical_formula_weight         553.46
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.375(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8905(4)
_cell_length_b                   22.4857(12)
_cell_length_c                   16.6825(8)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.61
_cell_volume                     2580.3(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0772
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50317
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_min         2.446
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1461 before and 0.0693 after correction. The Ratio of minimum to maximum transmission is 0.6937. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0761
_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^)+(0.0373P)^2^+3.3678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4489
_reflns_number_total             5936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02461_si_002.cif
_cod_data_source_block           b170515a_0m_a
_cod_depositor_comments
'Adding full bibliography for 4033256--4033257.cif.'
_cod_database_code               4033256
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.821
_shelx_estimated_absorpt_t_min   0.548
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16),
  C17(H17), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'