Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
Pan, Feng; Li, Haohu; Wang, Xiaohua; Luo, Liwen; Lin, Yanfei; Yu, Qingkai; Xie, Wenlin; Zhang, Lianpeng; RSC Advances 13 (2023) 13911–13918; doi:10.1039/D3RA02247A

data_7246792
_publ_section_title
;
 Synthesis of sulfur-containing
 benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted
 radical cyclization process
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              13911
_journal_page_last               13918
_journal_paper_doi               10.1039/D3RA02247A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C24 H20 Br N O3 S'
_chemical_formula_sum            'C24 H20 Br N O3 S'
_chemical_formula_weight         482.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-25 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                73.186(4)
_cell_angle_beta                 77.982(5)
_cell_angle_gamma                87.462(5)
_cell_formula_units_Z            4
_cell_length_a                   9.3901(8)
_cell_length_b                   15.1733(8)
_cell_length_c                   16.2514(7)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5000
_cell_measurement_theta_min      3.6110
_cell_volume                     2167.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -22.00  22.00   1.00    8.34    --  -15.89 -99.00-150.00   44
  2  \w     36.00  84.00   1.00    8.34    --   16.20  77.00-150.00   48
  3  \w    -52.00   7.00   1.00    8.34    --   16.20 -38.00 -90.00   59
  4  \w      0.00  83.00   1.00    8.34    --   16.20  57.00  90.00   83
  5  \w     43.00  70.00   1.00    8.34    --   16.20 178.00 -60.00   27
  6  \w     11.00  79.00   1.00    8.34    --   16.20  57.00-180.00   68
  7  \w    -24.00  53.00   1.00    8.34    --   16.20 -99.00   0.00   77
;
_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      0.0101679000
_diffrn_orient_matrix_UB_12      0.0473021000
_diffrn_orient_matrix_UB_13      -0.0043597000
_diffrn_orient_matrix_UB_21      -0.0361998000
_diffrn_orient_matrix_UB_22      0.0121595000
_diffrn_orient_matrix_UB_23      -0.0358169000
_diffrn_orient_matrix_UB_31      -0.0674712000
_diffrn_orient_matrix_UB_32      -0.0003478000
_diffrn_orient_matrix_UB_33      0.0294552000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16234
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                4496
_reflns_number_total             7620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ra02247a2.cif
_cod_data_source_block           20210608
_cod_database_code               7246792
_chemical_oxdiff_formula         'C H O N S Br'
_chemical_oxdiff_usercomment     'C H O N S P F Pt'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C14(H14), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C33(H33A,H33B), C38(H38A,H38B), C41(H41A,H41B), C43(H43A,
 H43B), C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C18(H18), C22(H22), C28(H28), C29(H29), C32(H32),
 C36(H36), C37(H37), C40(H40), C42(H42), C44(H44), C45(H45), C46(H46), C48(H48),
  C52(H52), C54(H54), C55(H55), C58(H58), C65(H65)
2.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C53(H53A,H53B,H53C)
;
_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 1.461
_oxdiff_exptl_absorpt_empirical_full_min 0.752