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_1556223
_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         'C21 H20 B F2 N3 O'
_chemical_formula_sum            'C21 H20 B F2 N3 O'
_chemical_formula_weight         379.21
_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             2013-07-09T22:39:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                81.335(15)
_cell_angle_beta                 74.018(16)
_cell_angle_gamma                72.150(16)
_cell_formula_units_Z            2
_cell_length_a                   8.2072(15)
_cell_length_b                   10.1894(18)
_cell_length_c                   11.851(2)
_cell_measurement_reflns_used    1738
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8168
_cell_measurement_theta_min      3.8831
_cell_measurement_wavelength     1.54184
_cell_volume                     904.5(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -38.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000   30.0000 107

  2 omega  -29.00   71.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000  -90.0000 100

  3 omega  -32.00   -5.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -57.0000 -120.0000 27

  4 omega  -31.00   70.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -57.0000  120.0000 101

  5 omega   35.00   62.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   90.0000 27

  6 omega   39.00   77.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   60.0000 38

  7 omega   78.00  158.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000  120.0000 80

  8 omega   33.00   58.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -32.0000  -78.0000 25

  9 omega   25.00  109.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -30.0000 84

 10 omega   45.00  103.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   60.0000 58

 11 omega   30.00   68.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 38

 12 omega   35.00   65.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 30

 13 omega   36.00   63.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  150.0000 27

 14 omega   34.00  112.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  -30.0000 78

 15 omega   31.00   66.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 35

 16 omega   37.00   70.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -30.0000 33

 17 omega   71.00  115.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -180.0000 44

 18 omega  109.00  141.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   30.0000 32

 19 omega   90.00  134.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -120.0000 44

 20 omega   33.00   60.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 27

 21 omega   41.00  125.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000  150.0000 84

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1902311
_diffrn_orient_matrix_UB_12      0.0050876
_diffrn_orient_matrix_UB_13      -0.05953
_diffrn_orient_matrix_UB_21      -0.0615396
_diffrn_orient_matrix_UB_22      0.1590453
_diffrn_orient_matrix_UB_23      -0.0019754
_diffrn_orient_matrix_UB_31      0.0376826
_diffrn_orient_matrix_UB_32      -0.0079793
_diffrn_orient_matrix_UB_33      0.1216426
_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  0.038
_diffrn_reflns_av_unetI/netI     0.1373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5436
_diffrn_reflns_theta_full        66.48
_diffrn_reflns_theta_max         66.48
_diffrn_reflns_theta_min         3.89
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.916
_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    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.1555
_exptl_crystal_size_mid          0.0664
_exptl_crystal_size_min          0.0351
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0544P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2320
_reflns_number_total             3164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401993p_si_005.cif
_cod_data_source_block           8acet
_cod_database_code               1556223