Visible-light-induced aerobic oxidative cyclization of nitroarenes with triethylamine using an organophotocatalyst.
Zhou, Yazheng; He, Yutong; Huang, Huawen; Deng, Guo-Jun; Organic & biomolecular chemistry 23 (2025) 1338–1341; doi:10.1039/d4ob01714e

data_7160307
_publ_section_title
;
 Visible-light-induced aerobic oxidative cyclization of nitroarenes with
 triethylamine using an organophotocatalyst.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1338
_journal_page_last               1341
_journal_paper_doi               10.1039/d4ob01714e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C10 H11 Br F N O2'
_chemical_formula_sum            'C10 H11 Br F N O2'
_chemical_formula_weight         276.11
_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             2023-12-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-09-29 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.740(3)
_cell_length_b                   7.5412(12)
_cell_length_c                   12.056(4)
_cell_measurement_reflns_used    976
_cell_measurement_temperature    292.99(10)
_cell_measurement_theta_max      23.0320
_cell_measurement_theta_min      3.1910
_cell_volume                     1092.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     71.00  97.00   1.00    8.00    --   12.05-178.00 120.00   26
  2  \w    -70.00  80.00   1.00    8.00    --   12.05   0.00-180.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0240087000
_diffrn_orient_matrix_UB_12      0.0559606000
_diffrn_orient_matrix_UB_13      -0.0324441000
_diffrn_orient_matrix_UB_21      0.0204706000
_diffrn_orient_matrix_UB_22      0.0565947000
_diffrn_orient_matrix_UB_23      0.0494130000
_diffrn_orient_matrix_UB_31      0.0498374000
_diffrn_orient_matrix_UB_32      -0.0503263000
_diffrn_orient_matrix_UB_33      0.0197663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.1315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4036
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.189
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.0060(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.0777
_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^)+(0.0887P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.2287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                825
_reflns_number_total             1907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01714e2.cif
_cod_data_source_block           5704-br
_cod_depositor_comments          'Adding full bibliography for 7160307.cif.'
_cod_database_code               7160307
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O2B)=Sof(H2B)=Sof(H7B)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(H7A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C7(H7A), C7(H7B), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
3.d Tetrahedral OH refined with riding coordinates:
 O2B(H2B)
3.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              43358
_olex2_date_sample_data_collection 2023-12-08
_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 15.001
_oxdiff_exptl_absorpt_empirical_full_min 0.209