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_1555600
_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_formula_moiety         'C19 H21 I N2 O'
_chemical_formula_sum            'C19 H21 I N2 O'
_chemical_formula_weight         420.28
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.735(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2720(10)
_cell_length_b                   9.1963(12)
_cell_length_c                   13.4788(18)
_cell_measurement_reflns_used    4699
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.01
_cell_measurement_theta_min      3.35
_cell_volume                     882.6(2)
_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 0.927
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3852
_diffrn_reflns_point_group_measured_fraction_full 0.722
_diffrn_reflns_point_group_measured_fraction_max 0.717
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.197
_diffrn_reflns_theta_min         3.349
_exptl_absorpt_coefficient_mu    14.293
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       blade
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.681
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.179
_refine_ls_abs_structure_details
;
 Flack x determined using 697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.278(13)
_refine_ls_extinction_coef       0.0038(12)
_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   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0648
_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^)+(0.1455P)^2^+0.0814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.1873
_reflns_Friedel_coverage         0.457
_reflns_Friedel_fraction_full    0.487
_reflns_Friedel_fraction_max     0.483
_reflns_number_gt                2273
_reflns_number_total             2307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01526_si_004.cif
_cod_data_source_block           cook120
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555600
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.062
_shelx_estimated_absorpt_t_max   0.627
_shelx_res_checksum              31948
_shelx_hkl_checksum              18645