Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature.
Do, Hien-Quang; Bachman, Shoshana; Bissember, Alex C.; Peters, Jonas C.; Fu, Gregory C.; Journal of the American Chemical Society 136 (2014) 2162–2167; doi:10.1021/ja4126609

data_4120590
_publ_section_title
;
 Photoinduced, copper-catalyzed alkylation of amides with unactivated
 secondary alkyl halides at room temperature.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2162
_journal_page_last               2167
_journal_paper_doi               10.1021/ja4126609
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C6 H8 Cu2 N2 O4)'
_chemical_formula_sum            'C12 H16 Cu4 N4 O8'
_chemical_formula_weight         598.45
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           122
_space_group_name_Hall           'I -4 2bw'
_space_group_name_H-M_alt        'I -4 2 d'
_symmetry_space_group_name_Hall  'I -4 2bw'
_symmetry_space_group_name_H-M   'I -4 2 d'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.2871(2)
_cell_length_b                   12.2871(2)
_cell_length_c                   46.5540(12)
_cell_measurement_temperature    100
_cell_volume                     7028.4(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            33381
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.863
_diffrn_reflns_theta_min         1.714
_exptl_absorpt_coefficient_mu    4.828
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.262
_exptl_crystal_description       block
_exptl_crystal_F_000             4736
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 1436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.8567P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.001
_reflns_number_gt                3603
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4126609_si_001.cif
_cod_data_source_block           crystal_001
_cod_original_cell_volume        7028.4(3)
_cod_database_code               4120590
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B), C11(H11A,H11B), C9(H9A,H9B), C6(H6A,H6B), C3(H3A,
 H3B), C8(H8A,H8B), C2(H2A,H2B)
;