Synthesis and reactivity of donor stabilized thionylium (SO2+) dications
Andrews, Ryan; De Backere, John; Stephan, Douglas W.; Chemical Communications  (2022) –; doi:10.1039/D2CC04129D

data_7130583
_publ_section_title
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 Synthesis and reactivity of donor stabilized thionylium (SO2+) dications
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04129D
_journal_year                    2022
_chemical_formula_moiety         'C21 H15 N3 O S, 2(C F3 O3 S), C2 H3 N'
_chemical_formula_sum            'C25 H18 F6 N4 O7 S3'
_chemical_formula_weight         696.61
_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
_audit_creation_date             2022-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                89.126(5)
_cell_angle_beta                 78.034(5)
_cell_angle_gamma                87.794(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5676(9)
_cell_length_b                   12.7491(10)
_cell_length_c                   13.1888(13)
_cell_measurement_reflns_used    3603
_cell_measurement_temperature    150.71
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.24
_cell_volume                     1408.2(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.71
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24139
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.128
_diffrn_reflns_theta_min         1.598
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0765 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9260.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       Needle
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.076
_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     427
_refine_ls_number_reflns         6741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0507P)^2^+0.5366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3948
_reflns_number_total             6741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04129d2.cif
_cod_data_source_block           ra034_a
_cod_database_code               7130583
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.958
_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,H,H,H) groups
2. Others
 Sof(N4)=1-FVAR(1)
 Sof(N24)=FVAR(1)
 Sof(C27)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(2)
 Sof(C5)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C7(H7), C3(H3), C1(H1), C10(H10), C4(H4), C21(H21),
 C11(H11), C14(H14), C18(H18), C13(H13), C12(H12), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C26(H26D,H26E,H26F), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'