Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes.
Niu, Songlin; Ulrich, Gilles; Retailleau, Pascal; Ziessel, Raymond; Organic letters 13 (2011) 4996–4999; doi:10.1021/ol201600s

data_1502335
_publ_section_title
;
 Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY
 dyes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4996
_journal_page_last               4999
_journal_paper_doi               10.1021/ol201600s
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C23 H25 B F2 I N3'
_chemical_formula_sum            'C23 H25 B F2 I N3'
_chemical_formula_weight         519.17
_chemical_name_systematic
; 
(E)-3-(4-(dimethylamino)styryl)-5,5-difluoro-8-iodo-1,7,9,10-
tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.68(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.429(7)
_cell_length_b                   9.844(7)
_cell_length_c                   27.51(2)
_cell_measurement_reflns_used    79
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      58.0
_cell_measurement_theta_min      6.9
_cell_volume                     2198(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 34
               Slice: 20.0000 - 190.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 42.0000 - 132.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 15
               Slice: 39.0000 - 114.0000
         Image width: 5.0000
            Exp time: 360.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8753
_diffrn_reflns_theta_full        47.99
_diffrn_reflns_theta_max         47.99
_diffrn_reflns_theta_min         6.69
_exptl_absorpt_coefficient_mu    11.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'little cube'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+4.8510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                1461
_reflns_number_total             2051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201600s_si_002.cif
_cod_data_source_block           compound_4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1502335