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_1556225
_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 H26 B1 F2 N3'
_chemical_formula_sum            'C25 H26 B F2 N'
_chemical_formula_weight         389.28
_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             2013-07-12T11:42:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                84.772(7)
_cell_angle_beta                 84.730(7)
_cell_angle_gamma                72.022(7)
_cell_formula_units_Z            2
_cell_length_a                   6.3964(5)
_cell_length_b                   10.0934(9)
_cell_length_c                   16.1699(14)
_cell_measurement_reflns_used    1867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9785
_cell_measurement_theta_min      2.7437
_cell_measurement_wavelength     1.54184
_cell_volume                     986.61(15)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega -115.00  -14.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -38.0000 -150.0000 101

  2 omega  -30.00   -4.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  125.0000  -60.0000 26

  3 omega -116.00  -14.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -35.0000  120.0000 102

  4 omega   47.00  158.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000   30.0000 111

  5 omega   43.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  150.0000 26

  6 omega   36.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 32

  7 omega   83.00  129.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  150.0000 46

  8 omega   41.00  118.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -120.0000 77

  9 omega   34.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -120.0000 25

 10 omega   37.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 26

 11 omega   34.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  150.0000 29

 12 omega   86.00  135.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  150.0000 49

 13 omega   30.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   30.0000 29

 14 omega   20.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000    0.0000 77

 15 omega    6.00   44.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000   90.0000 38

 16 omega   15.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000  120.0000 64

 17 omega   48.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -60.0000 43

 18 omega  128.00  154.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -150.0000 26

 19 omega   51.00   77.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   90.0000 26

 20 omega   42.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -180.0000 26

 21 omega  105.00  152.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  -90.0000 47

 22 omega   68.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -150.0000 41

 23 omega   47.00  103.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   90.0000 56

 24 omega   40.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   60.0000 29

 25 omega   40.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  -60.0000 81

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1348602
_diffrn_orient_matrix_UB_12      -0.1011966
_diffrn_orient_matrix_UB_13      0.066683
_diffrn_orient_matrix_UB_21      -0.1029514
_diffrn_orient_matrix_UB_22      0.1068075
_diffrn_orient_matrix_UB_23      0.0658539
_diffrn_orient_matrix_UB_31      -0.1888352
_diffrn_orient_matrix_UB_32      -0.0651898
_diffrn_orient_matrix_UB_33      0.0201513
_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_unetI/netI     0.0471
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6151
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         2.75
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.856
_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    1.31
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.4312
_exptl_crystal_size_mid          0.0575
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         6153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.093
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.5308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1871
_reflns_number_gt                4477
_reflns_number_total             6153
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol401993p_si_004.cif
_cod_data_source_block           8_dimetil_2
_cod_original_cell_volume        986.61(14)
_cod_database_code               1556225