Reversal of Diastereoselection in the Conjugate Addition of Cuprates to Unsaturated Lactams.
Wright, Stephen W.; Choi, Chulho; Chung, Seungwon; Boscoe, Brian P.; Drozda, Susan E.; Mousseau, James J.; Trzupek, John D.; Organic letters 17 (2015) 5204–5207; doi:10.1021/acs.orglett.5b02533

data_1555346
_publ_section_title
;
 Reversal of Diastereoselection in the Conjugate Addition of Cuprates to
 Unsaturated Lactams.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5204
_journal_page_last               5207
_journal_paper_doi               10.1021/acs.orglett.5b02533
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H15 N O2'
_chemical_formula_weight         169.22
_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                 102.426(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1254(3)
_cell_length_b                   6.9441(4)
_cell_length_c                   10.8047(6)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      69.79
_cell_measurement_theta_min      4.19
_cell_volume                     448.82(4)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_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  0.0748
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5783
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.618
_diffrn_reflns_theta_min         4.190
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             184
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
; 
 Flack x determined using 670 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(16)
_refine_ls_extinction_coef       0.051(9)
_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   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0767P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                1604
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02533_si_005.cif
_cod_data_source_block           Z594_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555346
_shelx_res_checksum              49139
_shelx_hkl_checksum              44390