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_1566828
_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         '2(F1.5 Sb0.25), C13 H11.5 N0.5 S0.5'
_chemical_formula_sum            'C13 H11.5 F3 N0.5 S0.5 Sb0.5'
_chemical_formula_weight         308.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 133.036(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.184(5)
_cell_length_b                   6.8384(13)
_cell_length_c                   19.415(4)
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.835
_cell_measurement_theta_min      2.871
_cell_volume                     2638.0(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10582
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.638
_diffrn_reflns_theta_min         3.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.182
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1500 before and 0.0401 after correction. The Ratio of minimum to maximum transmission is 0.8314. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.585
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0590
_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^)+(0.1278P)^2^+0.6385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             3204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01086k2.cif
_cod_data_source_block           mo_dm21091_0m
_cod_original_cell_volume        2638.1(9)
_cod_original_formula_sum        'C13 H11.50 F3 N0.50 S0.50 Sb0.50'
_cod_database_code               1566828
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.932
_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. Restrained distances
 F6-F4 \\sim F7-F5
 with sigma of 0.02
3. Rigid bond restraints
 Sb2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Sb2, F7, F6, F4, F5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F8, Sb2, F5, F6, F4, F7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
F6 \\sim F5 \\sim F4 \\sim F7 \\sim Sb2: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
F8 \\sim Sb2 \\sim F5 \\sim F6 \\sim F4 \\sim F7: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
Sb2 \\sim F8 \\sim F4 \\sim F6 \\sim F5 \\sim F7: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Fixed Sof: Sb2(0.25) H23A(0.5) H23B(0.5) H23C(0.5) F4(0.25) F7(0.25) F6(0.5)
 F5(0.25) F8(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C8(H8), C2(H2), C13(H13), C5(H5), C10(H10),
 C4(H4), C12(H12), C11(H11), C3(H3)
6.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              47598
_shelx_hkl_checksum              17037
_olex2_submission_special_instructions 'No special instructions were received'