8-Functionalization of alkyl-substituted-3,8-dimethyl BODIPYs by Knoevenagel condensation.
Palao, Eduardo; Agarrabeitia, Antonia R.; Bañuelos-Prieto, Jorge; Lopez, Teresa Arbeloa; Lopez-Arbeloa, Iñigo; Armesto, Diego; Ortiz, Maria J.; Organic letters 15 (2013) 4454–4457; doi:10.1021/ol401993p

data_1556222
_publ_section_title
;
 8-Functionalization of alkyl-substituted-3,8-dimethyl BODIPYs by
 Knoevenagel condensation.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4454
_journal_page_last               4457
_journal_paper_doi               10.1021/ol401993p
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H24 B F2 N3 O, C2 H6 O'
_chemical_formula_sum            'C25 H30 B F2 N3 O2'
_chemical_formula_weight         906.66
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-12T09:46:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                73.603(2)
_cell_angle_beta                 80.954(3)
_cell_angle_gamma                72.955(2)
_cell_formula_units_Z            4
_cell_length_a                   11.1938(4)
_cell_length_b                   12.4627(3)
_cell_length_c                   18.0716(7)
_cell_measurement_reflns_used    7424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.874
_cell_measurement_theta_min      3.803
_cell_measurement_wavelength     1.54184
_cell_volume                     2304.67(14)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2010)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -67.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756   57.0000 -150.0000 92

  2 omega -115.00  -20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -57.0000   60.0000 95

  3 omega  -89.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  110.0000  -72.0000 40

  4 omega   39.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000   30.0000 26

  5 omega  -35.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -38.0000  -90.0000 102

  6 omega   38.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -90.0000 31

  7 omega   41.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -180.0000 35

  8 omega   78.00  158.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000  120.0000 80

  9 omega   93.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000   60.0000 26

 10 omega   61.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000   60.0000 26

 11 omega   78.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  150.0000 26

 12 omega   37.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 28

 13 omega   30.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 34

 14 omega   46.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   60.0000 30

 15 omega   45.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   90.0000 64

 16 omega   33.00   59.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -120.0000 26

 17 omega   39.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000  -60.0000 91

 18 omega   32.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 33

 19 omega   48.00  154.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -120.0000 106

 20 omega   42.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -120.0000 25

 21 omega   70.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -120.0000 44

 22 omega   35.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -180.0000 34

 23 omega   33.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -30.0000 29

 24 omega   44.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -90.0000 55

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1204153
_diffrn_orient_matrix_UB_12      0.0302289
_diffrn_orient_matrix_UB_13      -0.0434558
_diffrn_orient_matrix_UB_21      0.0381089
_diffrn_orient_matrix_UB_22      0.0099887
_diffrn_orient_matrix_UB_23      0.0755794
_diffrn_orient_matrix_UB_31      0.0700482
_diffrn_orient_matrix_UB_32      -0.1296884
_diffrn_orient_matrix_UB_33      0.0186582
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8668
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         2.56
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2374
_exptl_crystal_size_mid          0.1668
_exptl_crystal_size_min          0.1461
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         8668
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.6482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                7214
_reflns_number_total             8668
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol401993p_si_002.cif
_cod_data_source_block           8acetam
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H60 B2 F4 N6 O4'
_cod_original_formula_weight         906.66
_cod_original_formula_moiety         'C50 H60 B2 F4 N6 O4'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2304.67(13)
_cod_database_code               1556222