Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N–N bonds
Ryan, Michael C.; Kim, Yeon Jung; Gerken, James B.; Wang, Fei; Aristov, Michael M.; Martinelli, Joseph R.; Stahl, Shannon S.; Chemical Science 11 (2020) 1170–1175; doi:10.1039/C9SC04305E

data_1556874
_publ_section_title
;
 Mechanistic insights into copper-catalyzed aerobic oxidative coupling of
 N--N bonds
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1170
_journal_page_last               1175
_journal_paper_doi               10.1039/C9SC04305E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C40 H34 Cu F12 N6 P2, 2(C4 H10 O)'
_chemical_formula_sum            'C48 H54 Cu F12 N6 O2 P2'
_chemical_formula_weight         1100.45
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2019-08-26 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.778(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.313(6)
_cell_length_b                   9.951(3)
_cell_length_c                   24.687(6)
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.125
_cell_measurement_theta_min      2.280
_cell_volume                     4986(2)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\ \w and 0.5\ \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            112793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.151
_diffrn_reflns_theta_min         1.107
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.2612
_exptl_absorpt_correction_T_min  0.2331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2268
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         11042
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0275
_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^+3.3876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9758
_reflns_number_total             11042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04305e2.cif
_cod_data_source_block           stahl236
_cod_depositor_comments
;Adding full bibliography for 1556874.cif.

 Adding full bibliography for 1556874.cif.
;
_cod_database_code               1556874
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Same fragment restrains
{C46, O2, C47A, C48A} sigma for 1-2: 0.01, 1-3: 0.02
as
{C46, O2, C47, C48}
3. Others
 Sof(C47A)=Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(1)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B), C47A(H47C,H47D)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5A), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32),
 C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
4.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C48(H48A,H48B,
 H48C), C48A(H48D,H48E,H48F)
;
_shelx_res_checksum              3286
_olex2_submission_special_instructions 'No special instructions were received'