Facile modification of phosphole-based aggregation-induced emission luminogens with sulfonyl isocyanates
König, Nils; Godínez-Loyola, Yokari; Yang, Fangshun; Laube, Christian; Laue, Michael; Lönnecke, Peter; Strassert, Cristian A.; Hey-Hawkins, Evamarie; Chemical Science 14 (2023) 2267–2274; doi:10.1039/D3SC00308F

data_1568554
_publ_section_title
;
 Facile modification of phosphole-based aggregation-induced emission
 luminogens with sulfonyl isocyanates
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2267
_journal_page_last               2274
_journal_paper_doi               10.1039/D3SC00308F
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H17 Cl N1 O2 P S,0.5(C2 H3 N)'
_chemical_formula_sum            'C23 H18.5 Cl N1.5 O2 P S'
_chemical_formula_weight         446.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-11 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.813(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0545(2)
_cell_length_b                   27.2503(6)
_cell_length_c                   18.9144(5)
_cell_measurement_reflns_used    6832
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.4720
_cell_measurement_theta_min      2.6160
_cell_volume                     4149.40(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
 or
 DIAMOND Version 4.5.3
 K. Brandenburg, Crystal Impact GbR, Bonn, Germany
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT-2018-2
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.3560
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13347
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        28.285
_diffrn_reflns_theta_max         30.228
_diffrn_reflns_theta_min         1.842
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       prism
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         13347
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.773
_reflns_Friedel_fraction_max     0.670
_reflns_number_gt                8958
_reflns_number_total             13347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00308f2.cif
_cod_data_source_block           comp_8a_x3313fin
_cod_original_sg_symbol_H-M      'C c'
_cod_original_formula_sum        'C23 H18.50 Cl N1.50 O2 P S'
_cod_database_code               1568554
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              17365