Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
Wu, Cunluo; Bian, Qilong; Ding, Tao; Tang, Mingming; Zhang, Wenkai; Xu, Yuanqing; Liu, Baoying; Xu, Hao; Li, Hai-Bei; Fu, Hua; ACS Catalysis  (2021) 9561–9568; doi:10.1021/acscatal.1c02272

data_4518903
_publ_section_title
;
 Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via
 Single-Electron Transfer
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9561
_journal_page_last               9568
_journal_paper_doi               10.1021/acscatal.1c02272
_journal_year                    2021
_chemical_formula_moiety         'C8 H6 N2 O2'
_chemical_formula_sum            'C8 H6 N2 O2'
_chemical_formula_weight         162.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.991(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4501(15)
_cell_length_b                   5.9208(10)
_cell_length_c                   15.748(3)
_cell_measurement_reflns_used    4663
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      5.32
_cell_volume                     775.9(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5543
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.221
_diffrn_reflns_theta_min         5.315
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0948P)^2^+0.1090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1305
_reflns_number_total             1397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02272_si_002.cif
_cod_data_source_block           1
_cod_database_code               4518903
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.867
_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:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_shelx_res_checksum              94496
_shelx_hkl_checksum              15627
_olex2_submission_special_instructions 'No special instructions were received'