Pd-Catalyzed Direct C-H Functionalization/Annulation of BODIPYs with Alkynes to Access Unsymmetrical Benzo[ b]-Fused BODIPYs: Discovery of Lysosome-Targeted Turn-On Fluorescent Probes.
Yang, Xiuguang; Jiang, Linfeng; Yang, Mufan; Zhang, Huaxing; Lan, Jingbo; Zhou, Fulin; Chen, Xingyu; Wu, Di; You, Jingsong; The Journal of organic chemistry 83 (2018) 9538–9546; doi:10.1021/acs.joc.8b01239

data_4035293
_publ_section_title
;
 Pd-Catalyzed Direct C-H Functionalization/Annulation of BODIPYs with
 Alkynes to Access Unsymmetrical Benzo[ b]-Fused BODIPYs: Discovery of
 Lysosome-Targeted Turn-On Fluorescent Probes.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9538
_journal_page_last               9546
_journal_paper_doi               10.1021/acs.joc.8b01239
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C44 H31 B F2 N2'
_chemical_formula_sum            'C44 H31 B F2 N2'
_chemical_formula_weight         636.52
_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     direct
_audit_creation_date             2018-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                96.328(3)
_cell_angle_beta                 104.212(3)
_cell_angle_gamma                92.839(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9158(4)
_cell_length_b                   12.3528(4)
_cell_length_c                   13.1488(5)
_cell_measurement_reflns_used    7045
_cell_measurement_temperature    139.3(3)
_cell_measurement_theta_max      72.5620
_cell_measurement_theta_min      4.2150
_cell_volume                     1702.85(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.3(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_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   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00   0.00   95
  2  \w   -104.00 -19.00   1.00    1.00    --  -36.04 -46.00  95.00   85
  3  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00 -60.00   84
  4  \w    -55.00  33.00   1.00    1.00    --  -36.04  38.00  90.00   88
  5  \w    -55.00  33.00   1.00    1.00    --  -36.04  38.00 -90.00   88
  6  \w     23.00  89.00   1.00    1.00    --   36.04-125.00 -30.00   66
  7  \w     23.00  89.00   1.00    1.00    --   36.04-125.00  90.00   66
  8  \w    -31.00  53.00   1.00    1.00    --   36.04 -57.00-180.00   84
  9  \w     23.00  89.00   1.00    1.00    --   36.04-125.00-180.00   66
 10  \w     40.00 126.00   1.00    1.57    --  108.71 -45.00 150.00   86
 11  \w     42.00 127.00   1.00    1.57    --  108.71 -61.00 -30.00   85
 12  \w     39.00 109.00   1.00    1.57    --  108.71 -94.00  90.00   70
 13  \w     39.00 109.00   1.00    1.57    --  108.71 -94.00-180.00   70
 14  \w     37.00 147.00   1.00    1.57    --  108.71 -15.00 -60.00  110
 15  \w    100.00 178.00   1.00    1.57    --  108.71 111.00-120.00   78
 16  \w     39.00 109.00   1.00    1.57    --  108.71 -94.00  60.00   70
 17  \w     91.00 176.00   1.00    1.57    --  108.71  61.00 -90.00   85
 18  \w     40.00 126.00   1.00    1.57    --  108.71 -45.00-120.00   86
 19  \w     39.00 115.00   1.00    1.57    --  108.71-111.00   0.00   76
 20  \w     91.00 177.00   1.00    1.57    --  108.71  45.00   0.00   86
 21  \w     82.00 176.00   1.00    1.57    --  108.71  77.00 -60.00   94
 22  \w     39.00 130.00   1.00    1.57    --  108.71 -30.00 120.00   91
 23  \w     39.00 109.00   1.00    1.57    --  108.71 -94.00 -90.00   70
 24  \w   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00-150.00   95
 25  \w   -104.00  -9.00   1.00    1.00    --  -36.04 -77.00  90.00   95
 26  \w    -55.00  33.00   1.00    1.00    --  -36.04  38.00   0.00   88
 27  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00-120.00   84
 28  \w      9.00 104.00   1.00    1.00    --   36.04  77.00   0.00   95
 29  \w     17.00 101.00   1.00    1.00    --   36.04  38.00-150.00   84
 30  \w    -31.00  53.00   1.00    1.00    --   36.04 -57.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0776411000
_diffrn_orient_matrix_UB_12      -0.0612365000
_diffrn_orient_matrix_UB_13      -0.0678840000
_diffrn_orient_matrix_UB_21      -0.0662718000
_diffrn_orient_matrix_UB_22      -0.1095232000
_diffrn_orient_matrix_UB_23      0.0110916000
_diffrn_orient_matrix_UB_31      -0.1044516000
_diffrn_orient_matrix_UB_32      0.0099801000
_diffrn_orient_matrix_UB_33      -0.1005675000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19010
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.877
_diffrn_reflns_theta_min         3.496
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0983P)^2^+0.6073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5608
_reflns_number_total             6634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01239_si_002.cif
_cod_data_source_block           yjs-yxg-1671-139k_sq
_cod_original_cell_volume        1702.86(11)
_cod_database_code               4035293
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.787
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00D(H00D), C00F(H00F), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C016(H016), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01C)
2.b Idealised Me refined as rotating group:
 C01E(H01D,H01E,H01F)
;
_shelx_res_checksum              30917
_shelx_hkl_checksum              37276
_shelx_fab_checksum              8390
_olex2_date_sample_data_collection 2018-01-22
_olex2_submission_special_instructions 'No special instructions were received'