Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis.
Tay, Nicholas E. S.; Nicewicz, David A.; Journal of the American Chemical Society 139 (2017) 16100–16104; doi:10.1021/jacs.7b10076

data_4131749
_publ_section_title
;
 Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic
 Photoredox Catalysis.
;
_journal_issue                   45
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16100
_journal_page_last               16104
_journal_paper_doi               10.1021/jacs.7b10076
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C14 H17 Cl N2'
_chemical_formula_sum            'C14 H17 Cl N2'
_chemical_formula_weight         248.74
_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     iterative
_audit_creation_date             2016-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.394(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1835(6)
_cell_length_b                   14.6901(10)
_cell_length_c                   11.1371(8)
_cell_measurement_reflns_used    6970
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.42
_cell_measurement_theta_min      3.01
_cell_volume                     1338.83(16)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13641
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.947
_diffrn_reflns_theta_min         4.983
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.347
_exptl_absorpt_correction_T_max  0.9055
_exptl_absorpt_correction_T_min  0.7717
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.8522.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0534P)^2^+0.3979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2385
_reflns_number_total             2631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10076_si_002.cif
_cod_data_source_block           x1605003
_cod_database_code               4131749
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.679
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              16691
_shelx_hkl_checksum              27693
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-17
_olex2_date_sample_submission    2016-05-17
_olex2_submission_original_sample_id 141-D
_olex2_submission_special_instructions 'No special instructions were received'