Silver-mediated, direct phosphorylation of BODIPY dyes at the 3- or 3,5-positions with H-phosphonates.
Lv, Fan; Li, Heng; Wu, Qinghua; Guo, Xing; Zhang, Hongtao; Yu, Changjiang; Jiao, Lijuan; Hao, Erhong; Chemical communications (Cambridge, England) 58 (2022) 3937–3940; doi:10.1039/d2cc00297c

data_7129755
_publ_section_title
;
 Silver-mediated, direct phosphorylation of BODIPY dyes at the 3- or
 3,5-positions with H-phosphonates.
;
_journal_issue                   24
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3937
_journal_page_last               3940
_journal_paper_doi               10.1039/d2cc00297c
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C22 H27 B F2 N2 O6 P2'
_chemical_formula_sum            'C22 H27 B F2 N2 O6 P2'
_chemical_formula_weight         526.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-18 deposited with the CCDC.	2022-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.7800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4985(5)
_cell_length_b                   15.0627(5)
_cell_length_c                   11.9448(4)
_cell_measurement_reflns_used    9576
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.97
_cell_volume                     2483.99(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      298.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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  0.0726
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            119295
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.971
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_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    1.407
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+2.0397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5030
_reflns_number_total             5704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00297c2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7129755.cif.'
_cod_database_code               7129755
_shelx_shelxl_version_number     2014/7
_publ_section_exptl
;
Any special experimental details
;
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.953
_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:
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00R(H00R)
2.b Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C), C00U(H00D,H00E,H00F), C00V(H00G,H00H,H00I), C00W(H00J,
 H00O,H00Q), C00X(H00S,H00T,H00U), C00Y(H00V,H00W,H00X), C00Z(H00Y,H,HA)
;
_shelx_res_checksum              93776
_olex2_submission_special_instructions 'No special instructions were received'