Direct C(sp2)–H amination of aryl aldehyde-derived hydrazones via visible light promoted photoredox catalysis
Zhu, Xin; He, Zhi; Li, Qiu-Yan; Wang, Xiao-Jun; RSC Advances 7 (2017) 25171–; doi:10.1039/C7RA01229B

data_7236502
_publ_section_title
;
 Direct C(sp2)--H amination of aryl aldehyde-derived hydrazones via
 visible light promoted photoredox catalysis
;
_journal_issue                   40
_journal_name_full               'RSC Advances'
_journal_page_first              25171
_journal_paper_doi               10.1039/C7RA01229B
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C20 H16 F3 N3 O3'
_chemical_formula_sum            'C20 H16 F3 N3 O3'
_chemical_formula_weight         403.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-11 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.520(4)
_cell_length_b                   13.946(3)
_cell_length_c                   13.312(3)
_cell_measurement_reflns_used    8781
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.4602
_cell_volume                     3623.9(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20719
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.921
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0339P)^2^+2.4370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3943
_reflns_number_total             4113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra01229b2.cif
_cod_data_source_block           a
_cod_original_cell_volume        3623.8(13)
_cod_database_code               7236502
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'