BODIPY(aryl)iodonium salts in the efficient synthesis of diversely functionalized BODIPYs and selective detection of serum albumin.
Kumar, Bintu; Bhatta, Anindita; Saraf, Prakriti; Pandurang, Taur Prakash; Rangan, Krishnan; Sarkar, Madhushree; Mitra, Sivaprasad; Kumar, Dalip; Organic & biomolecular chemistry 22 (2024) 3405–3414; doi:10.1039/d4ob00336e

data_7159866
_publ_section_title
;
 BODIPY(aryl)iodonium salts in the efficient synthesis of diversely
 functionalized BODIPYs and selective detection of serum albumin.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3405
_journal_page_last               3414
_journal_paper_doi               10.1039/d4ob00336e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C30 H33 B F2 I N2, C7 H7 O3 S, C H Cl3'
_chemical_formula_sum            'C38 H41 B Cl3 F2 I N2 O3 S'
_chemical_formula_weight         887.85
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-09-13 deposited with the CCDC.	2024-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                109.4650(10)
_cell_angle_beta                 94.5770(10)
_cell_angle_gamma                105.5260(10)
_cell_formula_units_Z            2
_cell_length_a                   8.40960(10)
_cell_length_b                   14.7442(2)
_cell_length_c                   17.5925(2)
_cell_measurement_reflns_used    16490
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.2650
_cell_measurement_theta_min      5.1820
_cell_volume                     1947.03(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_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      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     62.00  89.00   0.50    1.12    --    0.00  37.00-150.00   54
  2  \w    -48.00  24.00   0.50    1.12    --    0.00 -19.00-150.00  144
  3  \w    -70.00  18.00   0.50    1.12    --    0.00 -82.00-120.00  176
  4  \w    -18.00  50.00   0.50    1.12    --    0.00  37.00-150.00  136
  5  \w    -49.00  18.00   0.50    1.12    --    0.00 -37.00 -60.00  134
  6  \w     26.00  88.00   0.50    4.46    --  107.20 -45.00-150.00  124
  7  \w     36.00 132.00   0.50    4.46    --  107.20 -61.00  60.00  192
  8  \w    152.00 196.00   0.50    4.46    --  107.20  82.00   0.00   88
  9  \w     23.00 110.00   0.50    4.46    --  107.20 -61.00 -60.00  174
 10  \w     94.00 123.00   0.50    4.46    --  107.20 -82.00   0.00   58
 11  \w     80.00 197.00   0.50    4.46    --  107.20  15.00 150.00  234
 12  \w     21.00 100.00   0.50    4.46    --  107.20 -82.00  60.00  158
 13  \w     26.00 139.00   0.50    4.46    --  107.20 -82.00 -60.00  226
 14  \w     65.00 137.00   0.50    4.46    --  107.20 -82.00 150.00  144
 15  \w     18.00  56.00   0.50    4.46    --  107.20 -30.00-180.00   76
 16  \w     90.00 116.00   0.50    4.46    --  107.20 -82.00-150.00   52
 17  \w     79.00 104.00   0.50    4.46    --  107.20 -30.00-180.00   50
 18  \w     89.00 196.00   0.50    4.46    --  107.20  15.00-150.00  214
 19  \w     18.00 119.00   0.50    4.46    --  107.20 -30.00  30.00  202
 20  \w    100.00 125.00   0.50    4.46    --  107.20  61.00 -30.00   50
 21  \w    163.00 195.00   0.50    4.46    --  107.20  61.00 -30.00   64
 22  \w     63.00 128.00   0.50    4.46    --  107.20 -82.00  90.00  130
 23  \w     82.00 107.00   0.50    4.46    --  107.20  82.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1673500000
_diffrn_orient_matrix_UB_12      -0.0494912000
_diffrn_orient_matrix_UB_13      -0.0618370000
_diffrn_orient_matrix_UB_21      0.0954147000
_diffrn_orient_matrix_UB_22      0.0075175000
_diffrn_orient_matrix_UB_23      -0.0699913000
_diffrn_orient_matrix_UB_31      0.0183079000
_diffrn_orient_matrix_UB_32      -0.1054040000
_diffrn_orient_matrix_UB_33      -0.0145937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21257
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.880
_diffrn_reflns_theta_min         3.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       plate
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.863
_refine_diff_density_min         -1.903
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         8171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0662P)^2^+3.2322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7912
_reflns_number_total             8171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00336e3.cif
_cod_data_source_block           exp_814_c-h
_cod_depositor_comments          'Adding full bibliography for 7159866.cif.'
_cod_original_cell_volume        1947.03(4)
_cod_database_code               7159866
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C38 H41 B Cl3 F2 I N2 O3 S'
_shelx_estimated_absorpt_t_max   0.769
_shelx_estimated_absorpt_t_min   0.337
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 Ternary CH refined with riding coordinates:
 C22(H22), C28(H28), C25(H25), C38(H38)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C18(H18), C9(H9), C32(H32), C3(H3), C2(H2), C36(H36),
 C15(H15), C20(H20), C11(H11), C12(H12), C33(H33), C14(H14), C35(H35), C13(H13)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C27(H27A,H27B,H27C), C37(H37A,H37B,H37C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              44438
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.609