Total Synthesis of Macrocarpines D and E via an Enolate-Driven Copper-Mediated Cross-Coupling Process: Replacement of Catalytic Palladium with Copper Iodide.
Rahman, M. Toufiqur; Deschamps, Jeffrey R.; Imler, Gregory H.; Schwabacher, Alan W.; Cook, James M.; Organic letters 18 (2016) 4174–4177; doi:10.1021/acs.orglett.6b01526

data_1555599
_publ_section_title
;
 Total Synthesis of Macrocarpines D and E via an Enolate-Driven
 Copper-Mediated Cross-Coupling Process: Replacement of Catalytic
 Palladium with Copper Iodide.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4174
_journal_page_last               4177
_journal_paper_doi               10.1021/acs.orglett.6b01526
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H20 N2 O'
_chemical_formula_sum            'C19 H20 N2 O'
_chemical_formula_weight         292.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8328(5)
_cell_length_b                   11.6515(6)
_cell_length_c                   19.2975(7)
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.15
_cell_measurement_theta_min      2.74
_cell_volume                     1536.32(15)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX 2 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.147
_diffrn_reflns_theta_min         2.042
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prisim
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0606P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                3644
_reflns_number_total             4097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01526_si_005.cif
_cod_data_source_block           cook144
_cod_database_code               1555599
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014/6
_shelx_res_checksum              47028
_shelx_hkl_checksum              21063