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_4125404
_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         'C25 H34 Cu N2 O5, C8 H18 O2'
_chemical_formula_sum            'C33 H52 Cu N2 O7'
_chemical_formula_weight         652.30
_chemical_name_systematic        '[MeO2NN]CuOtBu'
_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                 90.730(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.8733(5)
_cell_length_b                   19.3641(7)
_cell_length_c                   26.6621(9)
_cell_measurement_reflns_used    6562
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.51
_cell_measurement_theta_min      2.24
_cell_volume                     7162.0(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_molecular_graphics    'SHELXTL v2014-4 (Bruker, 2014)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1266
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            65826
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.431
_diffrn_reflns_theta_min         1.528
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1216
_refine_ls_number_reflns         13195
_refine_ls_number_restraints     1664
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+11.5268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7620
_reflns_number_total             13195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09057_si_004.cif
_cod_data_source_block           MeO2NNCu-OtBu
_cod_database_code               4125404
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              691
_shelx_hkl_checksum              73723