Cu-Catalyzed Multicomponent Reaction of Styrenes, Perfluoroalkyl Halide, Alcohol, and tert-Butyl Hydroperoxide: One-Pot Synthesis of (Z)-β-Alkoxyperfluoroalkenone.
Luo, Qiang; Liu, Chunmei; Tong, Jingjing; Shao, Ying; Shan, Wenyu; Wang, Hanghang; Zheng, Hao; Cheng, Jiang; Wan, Xiaobing; The Journal of organic chemistry 81 (2016) 3103–3111; doi:10.1021/acs.joc.5b02664

data_4036542
_publ_section_title
;
 Cu-Catalyzed Multicomponent Reaction of Styrenes, Perfluoroalkyl Halide,
 Alcohol, and tert-Butyl Hydroperoxide: One-Pot Synthesis of
 (Z)-\b-Alkoxyperfluoroalkenone.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3103
_journal_page_last               3111
_journal_paper_doi               10.1021/acs.joc.5b02664
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H16 Cl F7 N4 O6'
_chemical_formula_sum            'C21 H16 Cl F7 N4 O6'
_chemical_formula_weight         588.83
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.7040(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1005(6)
_cell_length_b                   15.4782(8)
_cell_length_c                   11.8098(6)
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.56
_cell_volume                     2378.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26228
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+0.9225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                4032
_reflns_number_total             5482
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02664_si_002.cif
_cod_data_source_block           b140424b_0ma_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036542