Accessing oxy-functionalized N-heterocycles through rose bengal and TBHP integrated photoredox C(sp<sup>3</sup>)-O cross-coupling.
Mandal, Rahul Dev; Saha, Moumita; Das, Asish R.; Organic & biomolecular chemistry 20 (2022) 2939–2963; doi:10.1039/d2ob00381c

data_7158627
_publ_section_title
;
 Accessing oxy-functionalized N-heterocycles through rose bengal and TBHP
 integrated photoredox C(sp<sup>3</sup>)-O cross-coupling.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2939
_journal_page_last               2963
_journal_paper_doi               10.1039/d2ob00381c
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C36 H23 Br N4 O5'
_chemical_formula_sum            'C36 H23 Br N4 O5'
_chemical_formula_weight         671.49
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-08-18 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.723(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.543(3)
_cell_length_b                   10.328(2)
_cell_length_c                   22.564(5)
_cell_measurement_reflns_used    8891
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      2.56
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_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            44463
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.837
_exptl_absorpt_coefficient_mu    1.376
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5198
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       Square
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0098(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0509
_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^)+(0.1000P)^2^+0.5157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3433
_reflns_number_total             5462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00381c2.cif
_cod_data_source_block           MP
_cod_original_cell_volume        3101.0(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158627
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              9353