Photochemical and electrochemical regioselective cross-dehydrogenative C(sp2)–H sulfenylation and selenylation of substituted benzo[a]phenazin-5-ols
Nayek, Nayana; Karmakar, Pintu; Mandal, Mullicka; Karmakar, Indrajit; Brahmachari, Goutam; New Journal of Chemistry 46 (2022) 13483–13497; doi:10.1039/D2NJ02224A

data_7061597
_publ_section_title
;
 Photochemical and electrochemical regioselective cross-dehydrogenative
 C(sp2)--H sulfenylation and selenylation of substituted
 benzo[a]phenazin-5-ols
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13483
_journal_page_last               13497
_journal_paper_doi               10.1039/D2NJ02224A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C22 H14 N2 O S'
_chemical_formula_sum            'C22 H14 N2 O S'
_chemical_formula_weight         354.41
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2021-11-30 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.399(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9621(4)
_cell_length_b                   8.5724(3)
_cell_length_c                   14.8322(6)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    150.02(18)
_cell_measurement_theta_max      27.9140
_cell_measurement_theta_min      2.7390
_cell_volume                     1647.61(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.02(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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    -36.00  62.00   1.00  110.66    --   26.84 -37.00-180.00   98
  2  \w    -32.00  50.00   1.00  110.66    --   26.84 -60.00 -56.00   82
  3  \w     82.00 119.00   1.00  110.66    --   26.84 178.00   0.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0382393000
_diffrn_orient_matrix_UB_12      0.0222058000
_diffrn_orient_matrix_UB_13      -0.0325559000
_diffrn_orient_matrix_UB_21      -0.0108342000
_diffrn_orient_matrix_UB_22      -0.0797241000
_diffrn_orient_matrix_UB_23      -0.0088224000
_diffrn_orient_matrix_UB_31      -0.0376029000
_diffrn_orient_matrix_UB_32      0.0004589000
_diffrn_orient_matrix_UB_33      0.0339353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5264
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0673
_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^)+(0.1110P)^2^+0.4404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2057
_reflns_number_gt                2722
_reflns_number_total             3561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj02224a2.cif
_cod_data_source_block           gb_1852_lt_mo
_cod_depositor_comments          'Adding full bibliography for 7061597.cif.'
_cod_original_cell_volume        1647.60(10)
_cod_database_code               7061597
_chemical_oxdiff_formula         'C88 H56 N8 O4 S4'
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C13(H13), C11(H11), C18(H18), C6(H6), C10(H10), C3(H3), C19(H19),
 C5(H5), C20(H20), C21(H21), C4(H4), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2021-04-09
_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 4.454
_oxdiff_exptl_absorpt_empirical_full_min 0.649