Three-component selective synthesis of phenothiazines and bis-phenothiazines under metal-free conditions.
Chen, Shanping; Li, Zhuoqin; Hu, Kai; Feng, Wei; Mao, Guojiang; Xiao, Fuhong; Deng, Guo-Jun; Organic & biomolecular chemistry 21 (2023) 1920–1926; doi:10.1039/d3ob00055a

data_7159140
_publ_section_title
;
 Three-component selective synthesis of phenothiazines and
 bis-phenothiazines under metal-free conditions.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1920
_journal_page_last               1926
_journal_paper_doi               10.1039/d3ob00055a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H17 N S2'
_chemical_formula_sum            'C21 H17 N S2'
_chemical_formula_weight         347.48
_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     direct
_audit_creation_date             2021-09-26
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-09-29 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                83.056(7)
_cell_angle_beta                 82.898(6)
_cell_angle_gamma                89.355(6)
_cell_formula_units_Z            4
_cell_length_a                   7.6322(5)
_cell_length_b                   14.8230(11)
_cell_length_c                   15.0281(12)
_cell_measurement_reflns_used    4754
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1780
_cell_measurement_theta_min      2.0880
_cell_volume                     1674.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -55.00  34.00   1.00    2.00    --   12.05 -57.00-120.00   89
  2  \w    -19.00  80.00   1.00    2.00    --   12.05  77.00 150.00   99
  3  \w    -16.00  85.00   1.00    2.00    --   12.05  57.00  30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0492492000
_diffrn_orient_matrix_UB_12      0.0197778000
_diffrn_orient_matrix_UB_13      -0.0406680000
_diffrn_orient_matrix_UB_21      -0.0243701000
_diffrn_orient_matrix_UB_22      -0.0365841000
_diffrn_orient_matrix_UB_23      -0.0223395000
_diffrn_orient_matrix_UB_31      -0.0758397000
_diffrn_orient_matrix_UB_32      0.0243760000
_diffrn_orient_matrix_UB_33      -0.0119424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.166
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1076P)^2^+1.9245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4765
_reflns_number_total             5879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00055a2.cif
_cod_data_source_block           1471
_cod_depositor_comments          'Adding full bibliography for 7159140.cif.'
_cod_database_code               7159140
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.762(5)
 0.238(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C12(H12), C15(H15), C17(H17), C18(H18),
 C23(H23), C24(H24), C26(H26), C31(H31), C33(H33), C38(H38), C40(H40), C41(H41)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              80727
_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 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.458