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_1556226
_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         'C20 H19 B F2 N2 O'
_chemical_formula_sum            'C20 H19 B F2 N2 O'
_chemical_formula_weight         352.18
_space_group_crystal_system      triclinic
_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             2013-07-09T23:04:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                91.434(3)
_cell_angle_beta                 98.156(4)
_cell_angle_gamma                105.154(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4834(4)
_cell_length_b                   10.5795(4)
_cell_length_c                   11.2482(5)
_cell_measurement_reflns_used    3472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8268
_cell_measurement_theta_min      3.9753
_cell_measurement_wavelength     1.54184
_cell_volume                     849.07(7)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -19.00    7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -57.0000   90.0000 26

  2 omega  -34.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000  120.0000 101

  3 omega  -37.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000 -120.0000 103

  4 omega  -29.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -57.0000  -30.0000 98

  5 omega   83.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   30.0000 42

  6 omega   39.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 27

  7 omega   30.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -90.0000 38

  8 omega   31.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   90.0000 30

  9 omega   40.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -150.0000 38

 10 omega   30.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 37

 11 omega   50.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -30.0000 39

 12 omega   38.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   30.0000 27

 13 omega   48.00  155.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -120.0000 107

 14 omega   42.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -30.0000 30

 15 omega   24.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -120.0000 85

 16 omega   88.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -180.0000 32

 17 omega   35.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -120.0000 42

 18 omega   88.00  158.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000  -90.0000 70

 19 omega   40.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  120.0000 25

 20 omega   73.00  101.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000    0.0000 28

 21 omega   49.00  130.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   30.0000 81

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.202378
_diffrn_orient_matrix_UB_12      0.0115174
_diffrn_orient_matrix_UB_13      -0.0290585
_diffrn_orient_matrix_UB_21      -0.0304183
_diffrn_orient_matrix_UB_22      -0.0883619
_diffrn_orient_matrix_UB_23      -0.1160619
_diffrn_orient_matrix_UB_31      -0.0686187
_diffrn_orient_matrix_UB_32      -0.122131
_diffrn_orient_matrix_UB_33      0.0700725
_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  0.0189
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5196
_diffrn_reflns_theta_full        66.45
_diffrn_reflns_theta_max         66.45
_diffrn_reflns_theta_min         3.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.88
_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    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3012
_exptl_crystal_size_mid          0.0801
_exptl_crystal_size_min          0.0257
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0444P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                2652
_reflns_number_total             2977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401993p_si_006.cif
_cod_data_source_block           8meo
_cod_database_code               1556226