Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.
Zhang, Hai-Jun; Schuppe, Alexander W.; Pan, Shi-Tao; Chen, Jin-Xiang; Wang, Bo-Ran; Newhouse, Timothy R.; Yin, Liang; Journal of the American Chemical Society 140 (2018) 5300–5310; doi:10.1021/jacs.8b01886

data_4132152
_publ_section_title
;
 Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds
 with Air.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5300
_journal_page_last               5310
_journal_paper_doi               10.1021/jacs.8b01886
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H28 O3'
_chemical_formula_weight         328.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.4890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.47080(10)
_cell_length_b                   20.0417(4)
_cell_length_c                   7.2325(2)
_cell_measurement_reflns_used    6875
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      140.248
_cell_measurement_theta_min      8.824
_cell_volume                     894.60(3)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7525
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_min         4.412
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+0.1209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.886
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                2899
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01886_si_001.cif
_cod_data_source_block           cu_d8v17401_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132152
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.957
_shelxl_version_number           2013-4
_shelx_res_checksum              83732
_shelx_hkl_checksum              97908