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_4033257
_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         'C18 H19 Br N O2 S'
_chemical_formula_sum            'C18 H19 Br N O2 S'
_chemical_formula_weight         393.31
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.29 svn.r3433 for OlexSys, GUI svn.r5356)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.753(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2655(4)
_cell_length_b                   8.5522(4)
_cell_length_c                   27.6699(19)
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.2030
_cell_measurement_theta_min      3.8320
_cell_volume                     1707.37(17)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10659
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.82
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+31.7585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2483
_refine_ls_wR_factor_ref         0.2578
_reflns_number_gt                2752
_reflns_number_total             3476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02461_si_003.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 4033256--4033257.cif.'
_cod_database_code               4033257
_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:
 N1(H1), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'