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_1566827
_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         'C18 H10 F6 O6 S3'
_chemical_formula_sum            'C18 H10 F6 O6 S3'
_chemical_formula_weight         532.44
_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     dual
_audit_creation_date             2022-01-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                100.265(2)
_cell_angle_beta                 102.985(2)
_cell_angle_gamma                94.205(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4229(2)
_cell_length_b                   10.6178(2)
_cell_length_c                   12.2594(2)
_cell_measurement_reflns_used    14180
_cell_measurement_temperature    230(80)
_cell_measurement_theta_max      74.2270
_cell_measurement_theta_min      3.7540
_cell_volume                     1043.88(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230(80)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -16.00  49.00   0.50    2.00    --    0.00  36.00 -60.00  130
  2  \w     76.00 153.00   0.50    4.00    --   95.80  36.00 -60.00  154
  3  \w     89.00 115.00   0.50    4.00    --   95.80 -36.00 142.00   52
  4  \w     17.00  69.00   0.50    4.00    --   95.80 -36.00 142.00  104
  5  \w    -21.00   5.00   0.50    2.00    --    0.00 -57.00 150.00   52
  6  \w    -85.00 -26.00   0.50    2.00    --    0.00 -19.00  60.00  118
  7  \w     41.00  87.00   0.50    2.00    --    0.00  37.00 150.00   92
  8  \w    -53.00 -28.00   0.50    2.00    --    0.00 -36.00 142.00   50
  9  \w    -19.00  15.00   0.50    2.00    --    0.00  37.00 150.00   68
 10  \w     52.00  84.00   0.50    2.00    --    0.00  57.00-120.00   64
 11  \w    -22.00  42.00   0.50    2.00    --    0.00  57.00-120.00  128
 12  \w    -21.00   9.00   0.50    2.00    --    0.00  57.00-150.00   60
 13  \w    -29.00  25.00   0.50    2.00    --    0.00  77.00 150.00  108
 14  \w    -20.00  24.00   0.50    2.00    --    0.00 -19.00  60.00   88
 15  \w    -75.00 -50.00   0.50    2.00    --    0.00 -57.00 150.00   50
 16  \w     29.00  83.00   0.50    2.00    --    0.00  37.00   0.00  108
 17  \w     41.00  85.00   0.50    2.00    --    0.00  77.00 150.00   88
 18  \w    -19.00  16.00   0.50    2.00    --    0.00  37.00   0.00   70
 19  \w    126.00 152.00   0.50    4.00    --   95.80  61.00 101.41   52
 20  \w     71.00 108.00   0.50    4.00    --   95.80  61.00 101.41   74
 21  \w     48.00 128.00   0.50    4.00    --   95.80 -82.00  60.00  160
 22  \w    133.00 183.00   0.50    4.00    --   95.80  63.00-109.00  100
 23  \w     70.00 129.00   0.50    4.00    --   95.80  63.00-109.00  118
 24  \w      6.00  44.00   0.50    4.00    --   95.80 -82.00  60.00   76
 25  \w     65.00  91.00   0.50    4.00    --   95.80  77.00-150.00   52
 26  \w     64.00 185.00   0.50    4.00    --   95.80  82.00  90.00  242
 27  \w     75.00 152.00   0.50    4.00    --   95.80  45.00  60.00  154
 28  \w    160.00 185.00   0.50    4.00    --   95.80  45.00  60.00   50
 29  \w     11.00  46.00   0.50    4.00    --   95.80 -82.00 150.00   70
 30  \w     53.00 127.00   0.50    4.00    --   95.80 -82.00 150.00  148
 31  \w     75.00 169.00   0.50    4.00    --   95.80  45.00 150.00  188
 32  \w     71.00 184.00   0.50    4.00    --   95.80  61.00  30.00  226
 33  \w     72.00 110.00   0.50    4.00    --   95.80  61.00-120.00   76
 34  \w    136.00 167.00   0.50    4.00    --   95.80  61.00-120.00   62
 35  \w      6.00 121.00   0.50    4.00    --   95.80 -77.00   0.00  230
 36  \w    149.00 174.00   0.50    4.00    --   95.80  82.00  30.00   50
 37  \w     65.00  90.00   0.50    4.00    --   95.80  77.00 -60.00   50
 38  \w     65.00  90.00   0.50    4.00    --   95.80  77.00 -30.00   50
 39  \w     65.00  90.00   0.50    4.00    --   95.80  82.00  30.00   50
 40  \w     65.00  91.00   0.50    4.00    --   95.80  77.00  60.00   52
 41  \w    104.00 181.00   0.50    4.00    --   95.80  82.00 -60.00  154
 42  \w     63.00  91.00   0.50    4.00    --   95.80  82.00 -60.00   56
 43  \w     71.00 107.00   0.50    4.00    --   95.80  61.00-180.00   72
 44  \w     65.00  91.00   0.50    4.00    --   95.80  77.00  30.00   52
 45  \w     78.00 104.00   0.50    4.00    --   95.80  45.00  90.00   52
 46  \w    133.00 158.00   0.50    4.00    --   95.80  45.00  90.00   50
 47  \w     74.00 101.00   0.50    4.00    --   95.80  48.00  -6.58   54
 48  \w     68.00 118.00   0.50    4.00    --   95.80  69.00 154.93  100
 49  \w     65.00  90.00   0.50    4.00    --   95.80  77.00 120.00   50
 50  \w    138.00 163.00   0.50    4.00    --   95.80  77.00 150.00   50
 51  \w     73.00  98.00   0.50    4.00    --   95.80  56.00  -8.60   50
 52  \w    135.00 160.00   0.50    4.00    --   95.80  56.00  -8.60   50
 53  \w     71.00 119.00   0.50    4.00    --   95.80  61.00-150.00   96
 54  \w     75.00 126.00   0.50    4.00    --   95.80  61.00   0.00  102
 55  \w     71.00  96.00   0.50    4.00    --   95.80  61.00  60.00   50
 56  \w     69.00  94.00   0.50    4.00    --   95.80  67.00 -60.48   50
 57  \w     64.00  89.00   0.50    4.00    --   95.80  80.00-126.83   50
 58  \w     31.00 128.00   0.50    4.00    --   95.80 -82.00-150.00  194
 59  \w     42.00 111.00   0.50    4.00    --   95.80 -82.00 -60.00  138
 60  \w     65.00  91.00   0.50    4.00    --   95.80  77.00 -90.00   52
 61  \w     66.00  92.00   0.50    4.00    --   95.80  77.00   0.00   52
 62  \w     65.00  90.00   0.50    4.00    --   95.80  77.00-180.00   50
 63  \w     63.00  88.00   0.50    4.00    --   95.80  82.00  60.00   50
 64  \w     68.00  93.00   0.50    4.00    --   95.80  70.00  -1.05   50
 65  \w     75.00 183.00   0.50    4.00    --   95.80  45.00-150.00  216
 66  \w     65.00  91.00   0.50    4.00    --   95.80  77.00 150.00   52
 67  \w    160.00 185.00   0.50    4.00    --   95.80  77.00-150.00   50
 68  \w     75.00 101.00   0.50    4.00    --   95.80  49.00 -65.41   52
 69  \w    148.00 174.00   0.50    4.00    --   95.80  49.00 -65.41   52
 70  \w     74.00  99.00   0.50    4.00    --   95.80  48.00  99.25   50
 71  \w     64.00  90.00   0.50    4.00    --   95.80  82.00 120.00   52
;
_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      0.1201403000
_diffrn_orient_matrix_UB_12      0.1244400000
_diffrn_orient_matrix_UB_13      0.0473561000
_diffrn_orient_matrix_UB_21      -0.1384990000
_diffrn_orient_matrix_UB_22      0.0710384000
_diffrn_orient_matrix_UB_23      0.0364985000
_diffrn_orient_matrix_UB_31      0.0459992000
_diffrn_orient_matrix_UB_32      -0.0389713000
_diffrn_orient_matrix_UB_33      0.1172682000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22837
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.777
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0485P)^2^+0.4372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3393
_reflns_number_total             3692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           exp_2557
_cod_database_code               1566827
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.526
_shelx_estimated_absorpt_t_min   0.354
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_shelx_res_checksum              97421
_shelx_hkl_checksum              93773
_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 1.805
_oxdiff_exptl_absorpt_empirical_full_min 0.647