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_1555598
_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, 0.76(O)'
_chemical_formula_sum            'C19 H20 N2 O1.76'
_chemical_formula_weight         304.53
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   24.3768(13)
_cell_length_b                   24.3768(13)
_cell_length_c                   7.2197(5)
_cell_measurement_reflns_used    7019
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.414
_cell_measurement_theta_min      3.627
_cell_volume                     3715.4(4)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7328
_diffrn_reflns_point_group_measured_fraction_full 0.784
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.414
_diffrn_reflns_theta_min         3.626
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       rod
_exptl_crystal_F_000             1458.7
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.122
_refine_diff_density_max         1.708
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(2)
_refine_ls_extinction_coef       0.0034(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.776
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.776
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.1219
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3453
_refine_ls_wR_factor_ref         0.3510
_reflns_Friedel_coverage         0.544
_reflns_Friedel_fraction_full    0.582
_reflns_Friedel_fraction_max     0.532
_reflns_number_gt                2463
_reflns_number_total             2553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01526_si_002.cif
_cod_data_source_block           cook122b
_cod_original_cell_volume        3715.4(5)
_cod_database_code               1555598
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.927
_shelx_res_checksum              35488
_shelx_hkl_checksum              44166