Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position.
Lv, Fan; Guo, Xing; Wu, Hao; Li, Heng; Tang, Bing; Yu, Changjiang; Hao, Erhong; Jiao, Lijuan; Chemical communications (Cambridge, England) 56 (2020) 15577–15580; doi:10.1039/d0cc07259a

data_7127470
_publ_section_title
;
 Direct sulfonylation of BODIPY dyes with sodium sulfinates through
 oxidative radical hydrogen substitution at the \a-position.
;
_journal_issue                   99
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15577
_journal_page_last               15580
_journal_paper_doi               10.1039/d0cc07259a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H21 B F2 N2 O2 S'
_chemical_formula_sum            'C24 H21 B F2 N2 O2 S'
_chemical_formula_weight         450.334
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_audit_creation_date             2020-10-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-10-16 deposited with the CCDC.	2020-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7927(4)
_cell_length_b                   13.0246(5)
_cell_length_c                   19.6787(9)
_cell_measurement_reflns_used    9556
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.11
_cell_volume                     2253.63(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.9940
_diffrn_measured_fraction_theta_max 0.9932
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.9940
_diffrn_reflns_Laue_measured_fraction_max 0.9932
_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       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            92714
_diffrn_reflns_point_group_measured_fraction_full 0.9958
_diffrn_reflns_point_group_measured_fraction_max 0.9939
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.98
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0726 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.9380.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       plate
_exptl_crystal_F_000             936.983
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.2061
_refine_diff_density_min         -0.1932
_refine_diff_density_rms         0.0396
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_d_res_high            0.7674
_refine_ls_d_res_low             6.8340
_refine_ls_goodness_of_fit_ref   1.0620
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0620
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.5107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              25
_reflns_limit_l_min              -25
_reflns_number_gt                4976
_reflns_number_total             5196
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc07259a2.cif
_cod_data_source_block           mo_20190802a_0m
_cod_depositor_comments          'Adding full bibliography for 7127470.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7127470
_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:
 C00A(H00A), C00C(H00C), C00G(H00G), C00H(H00H), C00J(H00J), C00N(H00N),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W)
2.b Idealised Me refined as rotating group:
 C00M(H00b,H00d,H00e), C00P(H00f,H00i,H00k), C00U(H00l,H00m,H00o)
;
_olex2_submission_special_instructions 'No special instructions were received'