Experimental and mechanistic insights into copper(ii)–dioxygen catalyzed oxidative N-dealkylation of N-(2-pyridylmethyl)phenylamine and its derivatives
Wang, Yang; Liu, Haixiong; Zhang, Xiaofeng; Zhang, Zilong; Huang, Deguang; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02192E

data_7155934
_publ_section_title
;
 Experimental and mechanistic insights into copper(ii)--dioxygen catalyzed
 oxidative N-dealkylation of N-(2-pyridylmethyl)phenylamine and its
 derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02192E
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 Cu F3 N3 O4 S, C F3 S O3'
_chemical_formula_sum            'C20 H19 Cu F6 N3 O7 S2'
_chemical_formula_weight         655.04
_chemical_name_common            '[Cu(DPA-Ph)(H2O)(OTf)](OTf)'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-07-07 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.68300(16)
_cell_length_b                   10.2079(2)
_cell_length_c                   27.0713(6)
_cell_measurement_reflns_used    4141
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8410
_cell_measurement_theta_min      4.6230
_cell_volume                     2399.47(8)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6327
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    3.810
_exptl_absorpt_correction_T_max  0.5808
_exptl_absorpt_correction_T_min  0.3408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.4632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                3643
_reflns_number_total             3815
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02192e2.cif
_cod_data_source_block           full
_cod_database_code               7155934