Deprotonation of isoazatruxene enables photocatalytic arylation and phosphorylation of (hetero)aryl halides.
Zhou, Cen; Chen, Xi-Xian; An, Bohang; Wu, Ling-Wei; Cui, Hao; Zhang, Xiao; Organic & biomolecular chemistry 23 (2025) 9883–9889; doi:10.1039/d5ob00537j

data_7160586
_publ_section_title
;
 Deprotonation of isoazatruxene enables photocatalytic arylation and
 phosphorylation of (hetero)aryl halides.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9883
_journal_page_last               9889
_journal_paper_doi               10.1039/d5ob00537j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C13 H13 N O2'
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24
_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             2025-05-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-05-13 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.902(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5980(4)
_cell_length_b                   6.6697(2)
_cell_length_c                   14.8861(5)
_cell_measurement_reflns_used    5163
_cell_measurement_temperature    298.81(10)
_cell_measurement_theta_max      75.4060
_cell_measurement_theta_min      3.8500
_cell_volume                     1130.73(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.142a 64-bit (release 17-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.81(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.928
_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     33.00 119.00   0.50    0.15    --   45.63  52.00 176.00  172
  2  \w    116.00 176.00   0.50    0.62    --  103.81  61.00  90.00  120
  3  \w    109.00 134.00   0.50    0.62    --  103.81  52.00 176.00   50
  4  \w     33.00  62.00   0.50    0.62    --  103.81 -52.00  31.00   58
  5  \w     37.00  75.00   0.50    0.62    --  103.81 -61.00  60.00   76
  6  \w     37.00 104.00   0.50    0.62    --  103.81 -77.00 -30.00  134
  7  \w     44.00  73.00   0.50    0.62    --  103.81 -61.00-120.00   58
  8  \w    -26.00  53.00   0.50    0.15    --   45.63 -52.00  31.00  158
  9  \w    -89.00 -63.00   0.50    0.15    --  -45.63 -52.00  31.00   52
 10  \w   -171.00 -90.00   0.50    0.62    -- -103.81 -52.00  31.00  162
 11  \w   -172.00 -87.00   0.50    0.62    -- -103.81 -61.00 120.00  170
 12  \w   -107.00 -37.00   0.50    0.62    -- -103.81 125.00-150.00  140
 13  \w    -69.00 -32.00   0.50    0.62    -- -103.81  77.00 -60.00   74
 14  \w    -66.00 -35.00   0.50    0.62    -- -103.81  61.00-180.00   62
 15  \w    -98.00 -31.00   0.50    0.62    -- -103.81  77.00-150.00  134
 16  \w    -21.00  29.00   0.50    0.15    --  -45.63  19.00 -30.00  100
 17  \w    -29.00  27.00   0.50    0.15    --  -45.63  52.00 176.00  112
 18  \w    -67.00 -39.00   0.50    0.62    -- -103.81  61.00  90.00   56
 19  \w    -57.00 -32.00   0.50    0.62    -- -103.81  61.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1234863000
_diffrn_orient_matrix_UB_12      0.0426712000
_diffrn_orient_matrix_UB_13      -0.0558339000
_diffrn_orient_matrix_UB_21      -0.0539657000
_diffrn_orient_matrix_UB_22      -0.1377278000
_diffrn_orient_matrix_UB_23      0.0641922000
_diffrn_orient_matrix_UB_31      -0.0118156000
_diffrn_orient_matrix_UB_32      0.1804369000
_diffrn_orient_matrix_UB_33      0.0621979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6234
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.485
_diffrn_reflns_theta_min         3.881
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1143P)^2^+0.1294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1975
_reflns_number_total             2182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00537j2.cif
_cod_data_source_block           cxx-0429-1_auto
_cod_depositor_comments          'Adding full bibliography for 7160586.cif.'
_cod_database_code               7160586
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.846
_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:
 C4(H4), C8(H8), C12(H12), C13(H13), C2(H2), C9(H9), C5(H5)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              31539
_shelx_hkl_checksum              29999
_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 5.606
_oxdiff_exptl_absorpt_empirical_full_min 0.169