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_1566824
_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_absolute_configuration unk
_chemical_formula_moiety         'C11 H10 O S'
_chemical_formula_sum            'C11 H10 O S'
_chemical_formula_weight         190.25
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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                106.659(7)
_cell_angle_beta                 105.234(5)
_cell_angle_gamma                101.170(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0221(4)
_cell_length_b                   7.9102(7)
_cell_length_c                   9.5017(5)
_cell_measurement_reflns_used    4153
_cell_measurement_temperature    229(80)
_cell_measurement_theta_max      73.4170
_cell_measurement_theta_min      6.0250
_cell_volume                     466.74(6)
_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      229(80)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     55.00  80.00   0.50    2.00    --    0.00  82.00 150.00   50
  2  \w    -87.00 -57.00   0.50    2.00    --    0.00 -82.00 120.00   60
  3  \w    -32.00  19.00   0.50    2.00    --    0.00  82.00 150.00  102
  4  \w     15.00  77.00   0.50    2.00    --    0.00  37.00-120.00  124
  5  \w     20.00  87.00   0.50    2.00    --    0.00  57.00   0.00  134
  6  \w    -19.00   8.00   0.50    2.00    --    0.00  37.00-120.00   54
  7  \w    -23.00  11.00   0.50    2.00    --    0.00  57.00   0.00   68
  8  \w     39.00  64.00   0.50    2.00    --    0.00  37.00  90.00   50
  9  \w     -1.00  24.00   0.50    2.00    --    0.00 -82.00 120.00   50
 10  \w    -52.00 -26.00   0.50    2.00    --    0.00 -82.00 120.00   52
 11  \w    115.00 184.00   0.50    2.00    --   95.80  82.00-120.00  138
 12  \w     64.00  93.00   0.50    2.00    --   95.80  82.00-120.00   58
 13  \w     77.00 120.00   0.50    2.00    --   95.80  61.00   0.00   86
 14  \w      8.00 128.00   0.50    2.00    --   95.80 -82.00 -90.00  240
 15  \w    153.00 179.00   0.50    2.00    --   95.80  77.00-150.00   52
 16  \w     72.00 108.00   0.50    2.00    --   95.80  61.00 -60.00   72
 17  \w     63.00  88.00   0.50    2.00    --   95.80  82.00   0.00   50
 18  \w     77.00 124.00   0.50    2.00    --   95.80  30.00  90.00   94
 19  \w     29.00 127.00   0.50    2.00    --   95.80 -82.00  60.00  196
 20  \w     66.00  92.00   0.50    2.00    --   95.80  77.00 -60.00   52
 21  \w     71.00 116.00   0.50    2.00    --   95.80  61.00 -30.00   90
 22  \w     71.00 122.00   0.50    2.00    --   95.80  61.00 120.00  102
 23  \w     65.00  91.00   0.50    2.00    --   95.80  77.00 120.00   52
 24  \w     77.00 156.00   0.50    2.00    --   95.80  45.00-120.00  158
 25  \w     75.00 152.00   0.50    2.00    --   95.80  45.00 120.00  154
 26  \w    157.00 183.00   0.50    2.00    --   95.80  45.00 120.00   52
 27  \w    142.00 168.00   0.50    2.00    --   95.80  77.00 -30.00   52
 28  \w    128.00 175.00   0.50    2.00    --   95.80  61.00   0.00   94
 29  \w     71.00 123.00   0.50    2.00    --   95.80  61.00 150.00  104
 30  \w    128.00 182.00   0.50    2.00    --   95.80  61.00 150.00  108
 31  \w     72.00 103.00   0.50    2.00    --   95.80  61.00  60.00   62
 32  \w     66.00  92.00   0.50    2.00    --   95.80  77.00 -30.00   52
 33  \w    124.00 185.00   0.50    2.00    --   95.80  45.00 -60.00  122
 34  \w     75.00 101.00   0.50    2.00    --   95.80  45.00 -60.00   52
 35  \w     81.00 128.00   0.50    2.00    --   95.80 -82.00 150.00   94
 36  \w     68.00  94.00   0.50    2.00    --   95.80  77.00  30.00   52
 37  \w     17.00  47.00   0.50    2.00    --   95.80 -30.00   0.00   60
 38  \w     75.00 101.00   0.50    2.00    --   95.80  45.00 -90.00   52
 39  \w     48.00 115.00   0.50    2.00    --   95.80 -61.00 -90.00  134
 40  \w     66.00  96.00   0.50    2.00    --   95.80  77.00  60.00   60
 41  \w     65.00  91.00   0.50    2.00    --   95.80  77.00 150.00   52
 42  \w    103.00 128.00   0.50    2.00    --   95.80 -82.00  90.00   50
 43  \w      6.00  41.00   0.50    2.00    --   95.80 -61.00 -90.00   70
 44  \w     66.00 121.00   0.50    2.00    --   95.80  82.00 150.00  110
 45  \w     13.00  49.00   0.50    2.00    --   95.80 -82.00 150.00   72
 46  \w     67.00  92.00   0.50    2.00    --   95.80  77.00-150.00   50
 47  \w     63.00 115.00   0.50    2.00    --   95.80  82.00-180.00  104
 48  \w     73.00  98.00   0.50    2.00    --   95.80  53.00 -63.66   50
 49  \w     73.00 147.00   0.50    2.00    --   95.80  54.00  25.66  148
;
_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      -0.1542613000
_diffrn_orient_matrix_UB_12      -0.1763539000
_diffrn_orient_matrix_UB_13      -0.1304545000
_diffrn_orient_matrix_UB_21      0.1082687000
_diffrn_orient_matrix_UB_22      -0.1185177000
_diffrn_orient_matrix_UB_23      0.0772652000
_diffrn_orient_matrix_UB_31      -0.1448000000
_diffrn_orient_matrix_UB_32      -0.0022557000
_diffrn_orient_matrix_UB_33      0.0967681000
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6840
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.037
_diffrn_reflns_theta_max         67.037
_diffrn_reflns_theta_min         5.164
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53540
_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    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0794
_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^)+(0.1896P)^2^+0.2547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2415
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.773
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                2683
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           exp_2558
_cod_depositor_comments
;

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H20 O2 S2'
_cod_original_formula_weight         380.50
_cod_original_formula_moiety         '2(C11 H10 O S)'
_cod_original_formula_units_Z            1
_cod_database_code               1566824
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.739
_shelx_estimated_absorpt_t_min   0.542
_reflns_odcompleteness_completeness 99.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All S(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), C7(H7), C10(H10), C13(H13), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 S1(H1), S2(H2A)
;
_shelx_res_checksum              28506
_shelx_hkl_checksum              87340
_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 3.023
_oxdiff_exptl_absorpt_empirical_full_min 0.609