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_1566820
_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         'C48 H45 N S'
_chemical_formula_sum            'C48 H45 N S'
_chemical_formula_weight         667.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-10
_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                 113.172(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8923(2)
_cell_length_b                   13.29240(10)
_cell_length_c                   17.9856(3)
_cell_measurement_reflns_used    16974
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.1050
_cell_measurement_theta_min      4.2830
_cell_volume                     3712.68(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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -68.00  -6.00   1.00    1.00    --    0.00 -38.00  60.00   62
  2  \w    -89.00  15.00   1.00    1.00    --    0.00 -57.00 -60.00  104
  3  \w     38.00  77.00   1.00    1.00    --    0.00  38.00-180.00   39
  4  \w     39.00  89.00   1.00    1.00    --    0.00  38.00  60.00   50
  5  \w    -89.00  18.00   1.00    1.00    --    0.00 -38.00-180.00  107
  6  \w     89.00 120.00   1.00    2.00    --   95.80 -61.00-180.00   31
  7  \w      9.00  60.00   1.00    2.00    --   95.80 -61.00-180.00   51
  8  \w     53.00 114.00   1.00    2.00    --   95.80 -45.00  30.00   61
  9  \w     83.00 128.00   1.00    2.00    --   95.80 -82.00 -90.00   45
 10  \w     72.00 115.00   1.00    2.00    --   95.80 -30.00-120.00   43
 11  \w     14.00  54.00   1.00    2.00    --   95.80 -82.00 150.00   40
 12  \w     58.00 128.00   1.00    2.00    --   95.80 -82.00 150.00   70
 13  \w     52.00 102.00   1.00    2.00    --   95.80 -82.00  60.00   50
 14  \w     68.00 172.00   1.00    2.00    --   95.80  15.00  90.00  104
 15  \w     31.00  57.00   1.00    2.00    --   95.80 -30.00-120.00   26
 16  \w      6.00 120.00   1.00    2.00    --   95.80 -61.00 150.00  114
 17  \w     95.00 126.00   1.00    2.00    --   95.80 -82.00  30.00   31
 18  \w     76.00 185.00   1.00    2.00    --   95.80  30.00   0.00  109
 19  \w     23.00 122.00   1.00    2.00    --   95.80 -15.00-180.00   99
 20  \w     88.00 122.00   1.00    2.00    --   95.80 -82.00-150.00   34
 21  \w     46.00 121.00   1.00    2.00    --   95.80 -82.00   0.00   75
 22  \w     25.00  51.00   1.00    2.00    --   95.80 -45.00  30.00   26
 23  \w    115.00 140.00   1.00    2.00    --   95.80  30.00-150.00   25
 24  \w     92.00 117.00   1.00    2.00    --   95.80 -82.00 -60.00   25
 25  \w     26.00  73.00   1.00    2.00    --   95.80 -82.00  90.00   47
 26  \w     93.00 118.00   1.00    2.00    --   95.80 -82.00  90.00   25
 27  \w     60.00 117.00   1.00    2.00    --   95.80 -61.00-120.00   57
;
_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      -0.0243152000
_diffrn_orient_matrix_UB_12      0.0506447000
_diffrn_orient_matrix_UB_13      -0.0831374000
_diffrn_orient_matrix_UB_21      -0.0125868000
_diffrn_orient_matrix_UB_22      -0.1042588000
_diffrn_orient_matrix_UB_23      -0.0404180000
_diffrn_orient_matrix_UB_31      -0.0953519000
_diffrn_orient_matrix_UB_32      0.0007800000
_diffrn_orient_matrix_UB_33      -0.0116363000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40600
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.042
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84655
_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 green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0573P)^2^+1.2341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5804
_reflns_number_total             6597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           exp_2184
_cod_database_code               1566820
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.58
_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:
 C10(H10), C40(H40), C13(H13), C41(H41), C44(H44), C43(H43), C19(H19),
 C16(H16), C6(H6), C17(H17), C23(H23), C25(H25), C18(H18), C3(H3), C31(H31),
 C33(H33), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C46(H46A,H46B,
 H46C), C37(H37A,H37B,H37C), C48(H48A,H48B,H48C), C28(H28A,H28B,H28C), C47(H47A,
 H47B,H47C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              73523
_shelx_hkl_checksum              48860
_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.545