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_7158626
_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 H22 Cl2 N4 O5'
_chemical_formula_sum            'C36 H22 Cl2 N4 O5'
_chemical_formula_weight         661.47
_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
_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                92.200(7)
_cell_angle_beta                 101.408(7)
_cell_angle_gamma                92.387(7)
_cell_formula_units_Z            2
_cell_length_a                   8.346(4)
_cell_length_b                   12.269(6)
_cell_length_c                   14.899(7)
_cell_measurement_reflns_used    5760
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.72
_cell_volume                     1492.5(12)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.396
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_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^+0.9785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4292
_reflns_number_total             5261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00381c2.cif
_cod_data_source_block           ARDRDMCL_0m
_cod_original_cell_volume        1492.5(13)
_cod_database_code               7158626
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              84990