Ruthenium-catalyzed C-H bond activation and annulation of phenothiazine-3-carbaldehydes: facile access to dual-emission materials.
Liu, Junxiang; Wang, Kangmin; Wan, Liqiu; Yang, Xianhui; Li, Bijin; Chemical science 16 (2025) 3107–3113; doi:10.1039/d4sc07825j

data_1573703
_publ_section_title
;
 Ruthenium-catalyzed C-H bond activation and annulation of
 phenothiazine-3-carbaldehydes: facile access to dual-emission materials.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              3107
_journal_page_last               3113
_journal_paper_doi               10.1039/d4sc07825j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C71 H54 N5 O S, C F3 O3 S'
_chemical_formula_sum            'C72 H54 F3 N5 O4 S2'
_chemical_formula_weight         1174.32
_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             2024-05-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-10 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                100.582(2)
_cell_angle_beta                 94.663(2)
_cell_angle_gamma                108.170(2)
_cell_formula_units_Z            2
_cell_length_a                   11.8230(3)
_cell_length_b                   13.6657(3)
_cell_length_c                   23.0648(6)
_cell_measurement_reflns_used    14178
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      69.9930
_cell_measurement_theta_min      5.1800
_cell_volume                     3442.01(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_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    -20.00  60.00   1.00    1.49    --    0.00  77.00-150.00   80
  2  \w     27.00  65.00   1.00    1.49    --    0.00  57.00 -90.00   38
  3  \w    -10.00  32.00   1.00    1.49    --    0.00 -89.00  68.00   42
  4  \w    -12.00  80.00   1.00    5.95    --   54.00 -38.00 -90.00   92
  5  \w     19.00  53.00   1.00    5.95    --   54.00 -77.00 150.00   34
  6  \w     47.00 114.00   1.00    5.95    --   54.00  57.00-150.00   67
  7  \w     26.00 115.00   1.00    5.95    --   54.00  77.00 120.00   89
  8  \w     25.00 122.00   1.00    5.95    --   54.00  77.00  60.00   97
  9  \w     23.00  63.00   1.00    5.95    --   54.00-125.00 -60.00   40
 10  \w     46.00 111.00   1.00    5.95    --   54.00-125.00   0.00   65
 11  \w    101.00 135.00   1.00    5.95    --  108.00 -25.00-150.00   34
 12  \w     73.00 115.00   1.00    5.95    --  108.00 178.00-150.00   42
 13  \w     36.00 113.00   1.00    5.95    --  108.00-111.00-120.00   77
 14  \w     63.00 113.00   1.00    5.95    --  108.00-111.00  30.00   50
 15  \w    112.00 178.00   1.00    5.95    --  108.00  38.00  30.00   66
 16  \w     78.00 109.00   1.00    5.95    --  108.00 -38.00  90.00   31
 17  \w     47.00  73.00   1.00    5.95    --  108.00 -83.00-124.20   26
 18  \w     78.00 111.00   1.00    5.95    --  108.00-111.00 150.00   33
 19  \w     39.00  85.00   1.00    5.95    --  108.00 -50.00-150.00   46
 20  \w     83.00 112.00   1.00    5.95    --  108.00-111.00 -60.00   29
 21  \w     75.00 105.00   1.00    5.95    --  108.00  25.00  90.00   30
 22  \w    114.00 140.00   1.00    5.95    --  108.00  25.00  90.00   26
 23  \w    102.00 129.00   1.00    5.95    --  108.00 -50.00   0.00   27
 24  \w     83.00 113.00   1.00    5.95    --  108.00-111.00-180.00   30
 25  \w     37.00  72.00   1.00    5.95    --  108.00-111.00 -30.00   35
 26  \w     86.00 133.00   1.00    5.95    --  108.00  63.00   0.00   47
 27  \w     46.00 113.00   1.00    5.95    --  108.00-111.00  90.00   67
 28  \w     63.00 129.00   1.00    5.95    --  108.00 -38.00  30.00   66
 29  \w    119.00 150.00   1.00    5.95    --  108.00 178.00-120.00   31
 30  \w     64.00 129.00   1.00    5.95    --  108.00 -63.00-150.00   65
 31  \w     37.00  62.00   1.00    5.95    --  108.00 -38.00  90.00   25
 32  \w    104.00 129.00   1.00    5.95    --  108.00 -91.00-180.00   25
 33  \w    135.00 178.00   1.00    5.95    --  108.00 -12.00-180.00   43
 34  \w    127.00 175.00   1.00    5.95    --  108.00  25.00 150.00   48
 35  \w     55.00  85.00   1.00    5.95    --  108.00 -12.00-180.00   30
 36  \w     45.00 114.00   1.00    5.95    --  108.00 -77.00 150.00   69
 37  \w    120.00 161.00   1.00    5.95    --  108.00 111.00 -60.00   41
 38  \w    133.00 175.00   1.00    5.95    --  108.00  38.00-150.00   42
 39  \w     68.00 114.00   1.00    5.95    --  108.00 -63.00  30.00   46
 40  \w     96.00 122.00   1.00    5.95    --  108.00 -83.00-124.20   26
 41  \w     40.00  74.00   1.00    5.95    --  108.00 -63.00 -60.00   34
 42  \w    102.00 127.00   1.00    5.95    --  108.00 -63.00 -60.00   25
 43  \w     39.00 119.00   1.00    5.95    --  108.00 -77.00   0.00   80
 44  \w    101.00 127.00   1.00    5.95    --  108.00 111.00-180.00   26
 45  \w     87.00 139.00   1.00    5.95    --  108.00  50.00-120.00   52
 46  \w     87.00 177.00   1.00    5.95    --  108.00  50.00  90.00   90
 47  \w     83.00 121.00   1.00    5.95    --  108.00 -48.00 -26.05   38
 48  \w     93.00 122.00   1.00    5.95    --  108.00  38.00 -60.00   29
 49  \w    135.00 177.00   1.00    5.95    --  108.00  38.00 -60.00   42
 50  \w    100.00 130.00   1.00    5.95    --  108.00 -38.00 -60.00   30
 51  \w     69.00 120.00   1.00    5.95    --  108.00 -77.00 -90.00   51
 52  \w     44.00  82.00   1.00    5.95    --  108.00 -25.00  60.00   38
 53  \w     93.00 141.00   1.00    5.95    --  108.00 -25.00  60.00   48
 54  \w     88.00 113.00   1.00    5.95    --  108.00-111.00-150.00   25
 55  \w     69.00 107.00   1.00    5.95    --  108.00-111.00   0.00   38
 56  \w    145.00 176.00   1.00    5.95    --  108.00 111.00 -90.00   31
 57  \w     97.00 122.00   1.00    5.95    --  108.00 -89.00  68.00   25
 58  \w     45.00  72.00   1.00    5.95    --  108.00 -48.00 -26.05   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0666688000
_diffrn_orient_matrix_UB_12      -0.1127117000
_diffrn_orient_matrix_UB_13      -0.0370260000
_diffrn_orient_matrix_UB_21      -0.0751909000
_diffrn_orient_matrix_UB_22      -0.0242296000
_diffrn_orient_matrix_UB_23      0.0503375000
_diffrn_orient_matrix_UB_31      -0.0955635000
_diffrn_orient_matrix_UB_32      0.0388219000
_diffrn_orient_matrix_UB_33      -0.0285674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.293
_diffrn_reflns_theta_min         1.970
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_F_000             1224
_refine_diff_density_max         10.275
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.421
_refine_ls_extinction_coef       0.0027(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   3.328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         13073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.328
_refine_ls_R_factor_all          0.3465
_refine_ls_R_factor_gt           0.3244
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6657
_refine_ls_wR_factor_ref         0.6974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9985
_reflns_number_total             13073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07825j2.cif
_cod_data_source_block           20240514-libijin-jxl-22889-200k
_cod_depositor_comments          'Adding full bibliography for 1573703.cif.'
_cod_original_cell_volume        3442.01(15)
_cod_database_code               1573703
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C72 H54 O4 F3 N5 S2'
_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:
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00W(H00W),
 C00X(H00X), C00Z(H00Z), C010(H010), C012(H012), C014(H014), C015(H015),
 C016(H016), C01B(H01B), C01C(H01C), C01H(H01H), C01I(H01I), C01J(H01J),
 C01K(H01K), C01L(H01L), C01N(H01N), C01O(H01O), C01Q(H01Q), C01T(H01T),
 C01U(H01U), C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y), C020(H020),
 C021(H021), C022(H022), C023(H023), C024(H024), C025(H025), C026(H026),
 C027(H027), C028(H028), C029(H029), C02A(H02A), C02B(H02B), C02C(H02C),
 C02D(H02D), C02F(H02F), C02G(H02G), C02I(H02I), C02J(H02J), C02K(H02K)
2.b Idealised Me refined as rotating group:
 C01P(H01A,H01D,H01E), C01Z(H01F,H01G,H01M)
;
_shelx_res_checksum              92909
_shelx_hkl_checksum              67020
_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 3.004
_oxdiff_exptl_absorpt_empirical_full_min 0.469