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_1556227
_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         'C22 H23 B F2 N2 O'
_chemical_formula_sum            'C22 H23 B F2 N2 O'
_chemical_formula_weight         380.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-10T10:15:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.1680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.24780(10)
_cell_length_b                   18.8922(2)
_cell_length_c                   9.13090(10)
_cell_measurement_reflns_used    8515
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0229
_cell_measurement_theta_min      3.9896
_cell_measurement_wavelength     1.54184
_cell_volume                     1909.80(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -76.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5756  -38.0000  150.0000 59

  2 omega  -32.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -57.0000    0.0000 93

  3 omega   28.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756   38.0000  150.0000 87

  4 omega   30.00   64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -120.0000 34

  5 omega   30.00   55.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   90.0000 25

  6 omega   34.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000    0.0000 87

  7 omega   52.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   90.0000 25

  8 omega   46.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  120.0000 31

  9 omega   35.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -180.0000 30

 10 omega   35.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000   60.0000 27

 11 omega   46.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -150.0000 31

 12 omega   42.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000    0.0000 29

 13 omega   85.00  154.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   30.0000 69

 14 omega   26.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   90.0000 54

 15 omega  -37.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756  -77.0000  -90.0000 108

 16 omega   41.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5756 -125.0000 -180.0000 48

 17 omega   48.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -150.0000 61

 18 omega   38.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 27

 19 omega   33.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  150.0000 32

 20 omega   57.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  120.0000 49

 21 omega   59.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000    0.0000 41

 22 omega   25.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   60.0000 38

 23 omega   41.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000 -150.0000 26

 24 omega   84.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000 -150.0000 39

 25 omega   48.00   74.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -180.0000 26

 26 omega   87.00  154.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   15.0000 -180.0000 67

 27 omega  126.00  155.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -120.0000 29

 28 omega   84.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -180.0000 29

 29 omega   34.00   70.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -60.0000 36

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0957392
_diffrn_orient_matrix_UB_12      -0.0576791
_diffrn_orient_matrix_UB_13      0.0067455
_diffrn_orient_matrix_UB_21      0.0987063
_diffrn_orient_matrix_UB_22      -0.0495585
_diffrn_orient_matrix_UB_23      0.0816997
_diffrn_orient_matrix_UB_31      -0.0213586
_diffrn_orient_matrix_UB_32      0.0294313
_diffrn_orient_matrix_UB_33      0.1505226
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14615
_diffrn_reflns_theta_full        70.97
_diffrn_reflns_theta_max         70.97
_diffrn_reflns_theta_min         3.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.873
_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    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3009
_exptl_crystal_size_mid          0.0664
_exptl_crystal_size_min          0.0464
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0416P)^2^+0.6306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.083
_reflns_number_gt                3255
_reflns_number_total             3670
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401993p_si_003.cif
_cod_data_source_block           8meo_2
_cod_database_code               1556227