Divergent C(sp2)–H arylation of heterocycles via organic photoredox catalysis
Ren, Jie; Pi, Chao; Cui, Xiuling; Wu, Yangjie; Green Chemistry 24 (2022) 3017–3022; doi:10.1039/D1GC04825B

data_7244580
_publ_section_title
;
 Divergent C(sp2)--H arylation of heterocycles via organic photoredox
 catalysis
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              3017
_journal_page_last               3022
_journal_paper_doi               10.1039/D1GC04825B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.662(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3920(6)
_cell_length_b                   7.1332(4)
_cell_length_c                   20.1084(8)
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8070
_cell_measurement_theta_min      4.4000
_cell_volume                     2339.75(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -49.00 -22.00   1.00    1.50    --  -33.50 -77.00-180.00   27
  2  \w    -98.00 -33.00   1.00    1.50    --  -33.50 178.00-180.00   65
  3  \w      8.00  35.00   1.00    1.50    --  -33.50  37.00 150.00   27
  4  \w      4.00  33.00   1.00    1.50    --  -33.50  57.00  60.00   29
  5  \w    -55.00 -22.00   1.00    1.50    --  -33.50  37.00 150.00   33
  6  \w    -34.00  56.00   1.00    1.50    --   36.47 -37.00  90.00   90
  7  \w     25.00  50.00   1.00    1.50    --   36.47 -57.00-120.00   25
  8  \w     41.00  76.00   1.00    1.50    --   36.47 -99.00-180.00   35
  9  \w     29.00  70.00   1.00    1.50    --   36.47 -99.00 120.00   41
 10  \w     -3.00  23.00   1.00    1.50    --   36.47 -99.00 120.00   26
 11  \w    -27.00  13.00   1.00    1.50    --   36.47 -57.00-120.00   40
 12  \w    120.00 146.00   1.00    6.00    --  108.00 111.00-120.00   26
 13  \w    115.00 169.00   1.00    6.00    --  108.00 111.00   0.00   54
 14  \w     51.00 111.00   1.00    6.00    --  108.00-111.00 120.00   60
 15  \w    123.00 176.00   1.00    6.00    --  108.00  77.00-150.00   53
 16  \w     73.00 106.00   1.00    6.00    --  108.00 -94.00-180.00   33
 17  \w     92.00 149.00   1.00    6.00    --  108.00  61.00-150.00   57
 18  \w    109.00 168.00   1.00    6.00    --  108.00  61.00 120.00   59
 19  \w     91.00 160.00   1.00    6.00    --  108.00  45.00-180.00   69
 20  \w     41.00 128.00   1.00    6.00    --  108.00 -61.00  90.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0422225000
_diffrn_orient_matrix_UB_12      0.1933813000
_diffrn_orient_matrix_UB_13      -0.0038562000
_diffrn_orient_matrix_UB_21      -0.0841647000
_diffrn_orient_matrix_UB_22      -0.0959885000
_diffrn_orient_matrix_UB_23      -0.0004316000
_diffrn_orient_matrix_UB_31      0.0067161000
_diffrn_orient_matrix_UB_32      0.0091763000
_diffrn_orient_matrix_UB_33      0.0768810000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8634
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.322
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0680P)^2^+0.0639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3055
_reflns_number_total             4191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04825b2.cif
_cod_data_source_block           202105142
_cod_depositor_comments          'Adding full bibliography for 7244580.cif.'
_cod_original_cell_volume        2339.77(18)
_cod_database_code               7244580
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.898
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C1'(H1'), C2(H2), C2'(H2'), C3(H3), C3'(H3'), C4(H4), C4'(H4'),
 C10(H10), C10'(H10'), C11(H11), C11'(H11'), C12(H12), C12'(H12'), C13(H13),
 C13'(H13'), C14(H14), C14'(H14')
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15'(H15D,H15E,H15F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.893