Copper Catalyzed sp(3) C-H Etherification with Acyl Protected Phenols.
Salvador, Tolani K.; Arnett, Charles H.; Kundu, Subrata; Sapiezynski, Nicholas G.; Bertke, Jeffery A.; Raghibi Boroujeni, Mahdi; Warren, Timothy H.; Journal of the American Chemical Society 138 (2016) 16580–16583; doi:10.1021/jacs.6b09057

data_4125403
_publ_contact_author             'Timothy H. Warren'
_publ_section_title
;
 Copper Catalyzed sp(3) C-H Etherification with Acyl Protected Phenols.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16580
_journal_page_last               16583
_journal_paper_doi               10.1021/jacs.6b09057
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C28 H33 Cu N2 O4'
_chemical_formula_sum            'C28 H33 Cu N2 O4'
_chemical_formula_weight         525.10
_chemical_name_systematic        '[MeO2NN]Cu-tol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.8970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2015(10)
_cell_length_b                   12.9974(12)
_cell_length_c                   18.0731(16)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.1875
_cell_measurement_theta_min      2.332
_cell_volume                     2542.8(4)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_molecular_graphics
'XSEED; Barbour, L. J. (2001) J. Supramol. Chem. 1, 189-191.'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19849
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.942
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.810
_refine_diff_density_min         -1.201
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     250
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0634
_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^)+(0.1098P)^2^+15.1274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.1992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4019
_reflns_number_total             4486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09057_si_003.cif
_cod_data_source_block           MeO2NNCu-tol
_cod_database_code               4125403
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.814
_shelx_estimated_absorpt_t_max   0.892
_shelx_res_checksum              95867
_shelx_hkl_checksum              8281