Extended phenothiazines: synthesis, photophysical and redox properties, and efficient photocatalytic oxidative coupling of amines
Zhou, Jun; Mao, Lijun; Wu, Meng-Xiang; Peng, Zhiyong; Yang, Yiming; Zhou, Manfei; Zhao, Xiao-Li; Shi, Xueliang; Yang, Hai-Bo; Chemical Science  (2022) –; doi:10.1039/D2SC01086K

data_1566819
_publ_section_title
;
 Extended phenothiazines: synthesis, photophysical and redox properties,
 and efficient photocatalytic oxidative coupling of amines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01086K
_journal_year                    2022
_chemical_formula_moiety         'F6 Sb, C30 H25 N S'
_chemical_formula_sum            'C30 H25 F6 N S Sb'
_chemical_formula_weight         667.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-20 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.104(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8665(18)
_cell_length_b                   24.950(2)
_cell_length_c                   16.2233(13)
_cell_measurement_reflns_used    3192
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      69.2760
_cell_measurement_theta_min      3.3270
_cell_volume                     6341.4(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -23.00  55.00   1.00    5.00    --    0.00  19.00 -30.00   78
  2  \w    -82.00 -56.00   1.00    5.00    --    0.00 -38.00  30.00   26
  3  \w    -89.00 -18.00   1.00    5.00    --    0.00 -38.00-180.00   71
  4  \w    -27.00  16.00   1.00    5.00    --    0.00 -38.00  90.00   43
  5  \w    -52.00  18.00   1.00    5.00    --    0.00 -38.00  30.00   70
  6  \w    -62.00 -27.00   1.00    5.00    --    0.00 -38.00 -30.00   35
  7  \w      6.00 116.00   1.00    5.00    --   95.80 -45.00  90.00  110
  8  \w     70.00 114.00   1.00    5.00    --   95.80 -61.00-150.00   44
  9  \w     13.00  38.00   1.00    5.00    --   95.80 -82.00  90.00   25
 10  \w     95.00 120.00   1.00    5.00    --   95.80 -61.00 -60.00   25
 11  \w     32.00 103.00   1.00    5.00    --   95.80 -61.00  90.00   71
 12  \w     66.00 128.00   1.00    5.00    --   95.80 -82.00-150.00   62
 13  \w      9.00  35.00   1.00    5.00    --   95.80 -61.00 -60.00   26
 14  \w      7.00 110.00   1.00    5.00    --   95.80 -30.00-120.00  103
 15  \w     35.00  63.00   1.00    5.00    --   95.80 -61.00-150.00   28
 16  \w      7.00 110.00   1.00    5.00    --   95.80 -61.00   0.00  103
 17  \w    134.00 185.00   1.00    5.00    --   95.80  15.00  30.00   51
 18  \w     76.00 114.00   1.00    5.00    --   95.80 -82.00 150.00   38
 19  \w     82.00 107.00   1.00    5.00    --   95.80 -82.00 -90.00   25
 20  \w     77.00 126.00   1.00    5.00    --   95.80  30.00-150.00   49
 21  \w    157.00 183.00   1.00    5.00    --   95.80  30.00-150.00   26
 22  \w    125.00 183.00   1.00    5.00    --   95.80  30.00  90.00   58
 23  \w     69.00 106.00   1.00    5.00    --   95.80  15.00  30.00   37
 24  \w     61.00 118.00   1.00    5.00    --   95.80 -82.00  90.00   57
 25  \w     38.00 117.00   1.00    5.00    --   95.80 -82.00   0.00   79
 26  \w      8.00  73.00   1.00    5.00    --   95.80 -30.00-180.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0780857000
_diffrn_orient_matrix_UB_12      0.0321932000
_diffrn_orient_matrix_UB_13      -0.0420542000
_diffrn_orient_matrix_UB_21      0.0587129000
_diffrn_orient_matrix_UB_22      0.0474297000
_diffrn_orient_matrix_UB_23      -0.0127796000
_diffrn_orient_matrix_UB_31      0.0121994000
_diffrn_orient_matrix_UB_32      -0.0227915000
_diffrn_orient_matrix_UB_33      -0.0854955000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1462
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30155
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.331
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             2664
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.675
_refine_diff_density_min         -1.718
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0832P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3064
_reflns_number_total             5659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           exp_2096
_cod_database_code               1566819
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.567
_shelx_estimated_absorpt_t_min   0.213
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), C2(H2), C12(H12), C9(H9), C14(H14), C17(H17), C19(H19),
 C22(H22), C25(H25), C15(H15), C5(H5), C16(H16), C7(H7), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              99452
_shelx_hkl_checksum              35052
_shelx_fab_checksum              46572
_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 3.401
_oxdiff_exptl_absorpt_empirical_full_min 0.452