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_1566826
_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 H16 O2 S'
_chemical_formula_sum            'C18 H16 O2 S'
_chemical_formula_weight         296.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-21 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.5758(2)
_cell_length_b                   8.45120(10)
_cell_length_c                   18.7056(2)
_cell_measurement_reflns_used    18536
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.8850
_cell_measurement_theta_min      4.5020
_cell_volume                     3094.64(6)
_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      173.00(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     52.00  84.00   1.00    2.00    --    0.00  57.00  30.00   32
  2  \w    -30.00  61.00   1.00    2.00    --    0.00  77.00  30.00   91
  3  \w    -20.00  40.00   1.00    2.00    --    0.00  82.00 -30.00   60
  4  \w     50.00  87.00   1.00    2.00    --    0.00  37.00 -30.00   37
  5  \w    -16.00  18.00   1.00    2.00    --    0.00  37.00 -60.00   34
  6  \w     38.00  77.00   1.00    2.00    --    0.00  37.00 -60.00   39
  7  \w    -22.00  12.00   1.00    2.00    --    0.00  57.00  30.00   34
  8  \w     50.00  89.00   1.00    2.00    --    0.00  82.00 -30.00   39
  9  \w    -19.00  42.00   1.00    2.00    --    0.00  37.00 120.00   61
 10  \w     41.00  88.00   1.00    2.00    --    0.00  37.00-180.00   47
 11  \w    -17.00  19.00   1.00    2.00    --    0.00  37.00-180.00   36
 12  \w     46.00  89.00   1.00    2.00    --    0.00  37.00 120.00   43
 13  \w     42.00  88.00   1.00    2.00    --    0.00  37.00-120.00   46
 14  \w    -19.00  20.00   1.00    2.00    --    0.00  37.00-120.00   39
 15  \w    -19.00  19.00   1.00    2.00    --    0.00  37.00 -30.00   38
 16  \w     70.00 185.00   1.00    3.00    --   95.80  64.00-106.01  115
 17  \w     68.00  94.00   1.00    3.00    --   95.80  69.00  34.65   26
 18  \w    110.00 183.00   1.00    3.00    --   95.80  81.00 -42.04   73
 19  \w     68.00  94.00   1.00    3.00    --   95.80  69.00   1.98   26
 20  \w     66.00 105.00   1.00    3.00    --   95.80  75.00 110.57   39
 21  \w     63.00  88.00   1.00    3.00    --   95.80  81.00 -42.04   25
 22  \w    158.00 184.00   1.00    3.00    --   95.80  66.00 104.72   26
 23  \w    100.00 126.00   1.00    3.00    --   95.80  82.00-150.00   26
 24  \w     38.00 126.00   1.00    3.00    --   95.80 -82.00-120.00   88
 25  \w     63.00  89.00   1.00    3.00    --   95.80  82.00  60.00   26
 26  \w     63.00  88.00   1.00    3.00    --   95.80  82.00 150.00   25
 27  \w     65.00  91.00   1.00    3.00    --   95.80  77.00 -90.00   26
 28  \w    116.00 154.00   1.00    3.00    --   95.80  77.00 -90.00   38
 29  \w     63.00  88.00   1.00    3.00    --   95.80  82.00 -30.00   25
 30  \w     49.00  75.00   1.00    3.00    --   95.80 -82.00-150.00   26
 31  \w     63.00  91.00   1.00    3.00    --   95.80  82.00-150.00   28
 32  \w     89.00 128.00   1.00    3.00    --   95.80 -82.00 -60.00   39
 33  \w     66.00  92.00   1.00    3.00    --   95.80  75.00 -68.00   26
 34  \w      6.00 117.00   1.00    3.00    --   95.80 -61.00  60.00  111
 35  \w     71.00 183.00   1.00    3.00    --   95.80  70.00 -57.06  112
 36  \w     67.00  92.00   1.00    3.00    --   95.80  72.00-179.48   25
 37  \w    115.00 185.00   1.00    3.00    --   95.80  63.00 157.41   70
 38  \w     65.00  91.00   1.00    3.00    --   95.80  77.00-150.00   26
 39  \w     63.00  88.00   1.00    3.00    --   95.80  82.00  90.00   25
 40  \w    156.00 185.00   1.00    3.00    --   95.80  82.00  90.00   29
 41  \w     63.00  88.00   1.00    3.00    --   95.80  82.00   0.00   25
 42  \w    114.00 144.00   1.00    3.00    --   95.80  82.00   0.00   30
 43  \w     63.00  88.00   1.00    3.00    --   95.80  82.00 -90.00   25
 44  \w     65.00  90.00   1.00    3.00    --   95.80  77.00 150.00   25
 45  \w     64.00  90.00   1.00    3.00    --   95.80  82.00 120.00   26
 46  \w     79.00 128.00   1.00    3.00    --   95.80 -82.00 123.19   49
 47  \w     71.00 184.00   1.00    3.00    --   95.80  61.00-180.00  113
 48  \w     69.00 116.00   1.00    3.00    --   95.80  66.00-116.68   47
 49  \w     65.00  91.00   1.00    3.00    --   95.80  77.00  60.00   26
 50  \w     63.00  89.00   1.00    3.00    --   95.80  82.00-120.00   26
 51  \w     65.00  90.00   1.00    3.00    --   95.80  77.00-180.00   25
 52  \w     63.00  88.00   1.00    3.00    --   95.80  82.00-180.00   25
 53  \w     71.00  97.00   1.00    3.00    --   95.80  61.00 -90.00   26
 54  \w     65.00 100.00   1.00    3.00    --   95.80  77.00 -30.00   35
 55  \w     37.00 117.00   1.00    3.00    --   95.80 -82.00  60.00   80
 56  \w     71.00 118.00   1.00    3.00    --   95.80  61.00  60.00   47
 57  \w    125.00 185.00   1.00    3.00    --   95.80  61.00  60.00   60
 58  \w     65.00 145.00   1.00    3.00    --   95.80  77.00 120.00   80
 59  \w    153.00 178.00   1.00    3.00    --   95.80  77.00 120.00   25
 60  \w     16.00  83.00   1.00    3.00    --   95.80 -77.00 -90.00   67
 61  \w     94.00 121.00   1.00    3.00    --   95.80 -77.00 -90.00   27
 62  \w     73.00 142.00   1.00    3.00    --   95.80  52.00 -66.93   69
 63  \w    104.00 153.00   1.00    3.00    --   95.80  60.00  29.46   49
 64  \w     63.00  89.00   1.00    3.00    --   95.80  82.00 -60.00   26
 65  \w    100.00 180.00   1.00    3.00    --   95.80  82.00  30.00   80
 66  \w     69.00  94.00   1.00    3.00    --   95.80  66.00  62.74   25
 67  \w     75.00 181.00   1.00    3.00    --   95.80  45.00   0.00  106
 68  \w     63.00  88.00   1.00    3.00    --   95.80  82.00  30.00   25
 69  \w     89.00 126.00   1.00    3.00    --   95.80 -82.00-150.00   37
 70  \w     63.00  89.00   1.00    3.00    --   95.80  81.00-170.98   26
 71  \w     71.00  97.00   1.00    3.00    --   95.80  60.00  29.46   26
 72  \w     70.00  98.00   1.00    3.00    --   95.80  63.00 157.41   28
 73  \w     69.00  94.00   1.00    3.00    --   95.80  66.00 104.72   25
 74  \w     72.00 176.00   1.00    3.00    --   95.80  55.00 111.64  104
;
_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      -0.0321498000
_diffrn_orient_matrix_UB_12      -0.0485875000
_diffrn_orient_matrix_UB_13      0.0718592000
_diffrn_orient_matrix_UB_21      -0.0705166000
_diffrn_orient_matrix_UB_22      0.0545690000
_diffrn_orient_matrix_UB_23      -0.0269837000
_diffrn_orient_matrix_UB_31      -0.0137473000
_diffrn_orient_matrix_UB_32      -0.1670640000
_diffrn_orient_matrix_UB_33      -0.0297497000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            69070
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.517
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43315
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0332P)^2^+1.5919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2595
_reflns_number_total             2759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           exp_2548
_cod_database_code               1566826
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.685
_shelx_estimated_absorpt_t_min   0.587
_reflns_odcompleteness_completeness 99.94
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              53170
_shelx_hkl_checksum              60117
_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 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.459