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_1556224
_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'
_chemical_formula_sum            'C23 H24 B F2 N3 O'
_chemical_formula_weight         407.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-09T13:09:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 117.842(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.6729(10)
_cell_length_b                   7.6463(2)
_cell_length_c                   22.0381(7)
_cell_measurement_reflns_used    6677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9249
_cell_measurement_theta_min      3.3513
_cell_measurement_wavelength     1.54184
_cell_volume                     3974.3(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -35.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000   30.0000 87

  2 omega   21.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   38.0000  150.0000 91

  3 omega   41.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000  -30.0000 50

  4 omega   44.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000    0.0000 32

  5 omega   26.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -120.0000 68

  6 omega   49.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -30.0000 28

  7 omega   30.00   68.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   30.0000 38

  8 omega   29.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -25.0000   60.0000 37

  9 omega   30.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -90.0000 32

 10 omega   32.00   58.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 26

 11 omega   88.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  -60.0000 25

 12 omega   62.00  139.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000   30.0000 77

 13 omega   30.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 39

 14 omega   37.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  150.0000 39

 15 omega  -16.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -99.0000 -180.0000 82

 16 omega  -24.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000 -120.0000 62

 17 omega    9.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000    0.0000 39

 18 omega   46.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -30.0000 63

 19 omega  130.00  157.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   30.0000 27

 20 omega   56.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -150.0000 56

 21 omega   34.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -120.0000 32

 22 omega   60.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   60.0000 44

 23 omega   79.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000   30.0000 32

 24 omega   43.00   68.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -180.0000 25

 25 omega   40.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000  -90.0000 31

 26 omega  101.00  127.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000  -90.0000 26

 27 omega   51.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -150.0000 45

 28 omega  105.00  156.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -150.0000 51

 29 omega   32.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 37

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0550588
_diffrn_orient_matrix_UB_12      0.0525128
_diffrn_orient_matrix_UB_13      0.001872
_diffrn_orient_matrix_UB_21      -0.0282804
_diffrn_orient_matrix_UB_22      0.0389858
_diffrn_orient_matrix_UB_23      -0.0775217
_diffrn_orient_matrix_UB_31      -0.0208565
_diffrn_orient_matrix_UB_32      -0.1905421
_diffrn_orient_matrix_UB_33      -0.0153702
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14384
_diffrn_reflns_theta_full        71.99
_diffrn_reflns_theta_max         71.99
_diffrn_reflns_theta_min         3.75
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
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    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.4651
_exptl_crystal_size_mid          0.0846
_exptl_crystal_size_min          0.0311
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+3.0963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                3343
_reflns_number_total             3896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401993p_si_007.cif
_cod_data_source_block           8aceto
_cod_original_cell_volume        3974.3(2)
_cod_database_code               1556224