Copper-Catalyzed Cascade Radical Addition–Cyclization Halogen Atom Transfer between Alkynes and Unsaturated α-Halogenocarbonyls
Gao, Yuzhen; Zhang, Pengbo; Ji, Zhe; Tang, Guo; Zhao, Yufen; ACS Catalysis  (2016) 186–; doi:10.1021/acscatal.6b03033

data_4513995
_publ_section_title
;
 Copper-Catalyzed Cascade Radical Addition--Cyclization Halogen Atom
 Transfer between Alkynes and Unsaturated \a-Halogenocarbonyls
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              186
_journal_paper_doi               10.1021/acscatal.6b03033
_journal_year                    2016
_chemical_formula_sum            'C18 H20 Br Cl O4'
_chemical_formula_weight         415.70
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.405(5)
_cell_angle_beta                 96.467(5)
_cell_angle_gamma                113.588(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6779(5)
_cell_length_b                   9.0204(6)
_cell_length_c                   12.8020(6)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      62.211
_cell_measurement_theta_min      5.35
_cell_volume                     908.37(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4761
_diffrn_reflns_theta_full        62.19
_diffrn_reflns_theta_max         62.19
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    4.599
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.32225
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.939
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1173P)^2^+0.2616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1657
_reflns_number_gt                2614
_reflns_number_total             2813
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs6b03033_si_002.cif
_cod_data_source_block           t0830
_cod_original_cell_volume        908.37(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4513995