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_1566825
_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         'C26 H23 N S'
_chemical_formula_sum            'C26 H23 N S'
_chemical_formula_weight         381.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-28 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                   23.8497(9)
_cell_length_b                   21.8615(7)
_cell_length_c                   7.9142(3)
_cell_measurement_reflns_used    4242
_cell_measurement_temperature    201(40)
_cell_measurement_theta_max      72.7470
_cell_measurement_theta_min      3.6830
_cell_volume                     4126.4(3)
_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      201(40)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  49.00   0.50    2.00    --    0.00  16.00 -29.00   52
  2  \w    -32.00  -7.00   0.50    2.00    --    0.00 -16.00 160.00   50
  3  \w    127.00 152.00   0.50   10.00    --   95.80  16.00 -29.00   50
  4  \w     92.00 119.00   0.50   10.00    --   95.80 -16.00 160.00   54
  5  \w    -66.00  21.00   0.50    2.00    --    0.00 -57.00  60.00  174
  6  \w    -60.00 -30.00   0.50    2.00    --    0.00 -37.00   0.00   60
  7  \w     84.00 182.00   0.50   10.00    --   95.80  30.00  60.00  196
  8  \w     56.00 107.00   0.50   10.00    --   95.80 -82.00 -30.00  102
  9  \w      8.00  34.00   0.50   10.00    --   95.80 -82.00 -30.00   52
 10  \w      7.00  90.00   0.50   10.00    --   95.80 -30.00  90.00  166
 11  \w     79.00 104.00   0.50   10.00    --   95.80  30.00-150.00   50
 12  \w    121.00 147.00   0.50   10.00    --   95.80  30.00-150.00   52
 13  \w     14.00 114.00   0.50   10.00    --   95.80 -61.00  30.00  200
;
_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      -0.0445297000
_diffrn_orient_matrix_UB_12      -0.0505982000
_diffrn_orient_matrix_UB_13      -0.0180589000
_diffrn_orient_matrix_UB_21      -0.0448418000
_diffrn_orient_matrix_UB_22      0.0487576000
_diffrn_orient_matrix_UB_23      -0.0386521000
_diffrn_orient_matrix_UB_31      0.0133256000
_diffrn_orient_matrix_UB_32      -0.0051118000
_diffrn_orient_matrix_UB_33      -0.1900000000
_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  0.0673
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16520
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.707
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64509
_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    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0834
_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^)+(0.0806P)^2^+9.4770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2974
_reflns_number_total             3670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           exp_2556
_cod_database_code               1566825
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.623
_reflns_odcompleteness_completeness 99.71
_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. Rigid bond restraints
 C15, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C14 \\sim C15: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C16 \\sim C15: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C10(H10), C2(H2), C8(H8), C21(H21), C22(H22), C18(H18),
 C19(H19), C12(H12), C5(H5), C11(H11), C3(H3), C4(H4)
4.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              8653
_shelx_hkl_checksum              30093
_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.655