Chemistry at Boron: Synthesis and Properties of Red to Near-IR Fluorescent Dyes Based on Boron-Substituted Diisoindolomethene Frameworks
Gilles Ulrich; Sébastien Goeb; Antoinette De Nicola; Pascal Retailleau; Raymond Ziessel; Journal of Organic Chemistry 76 (2011) 4489–4505; doi:10.1021/jo200246q

data_4026355
_publ_section_title
;
 Chemistry at Boron: Synthesis and Properties of Red to Near-IR
 Fluorescent Dyes Based on Boron-Substituted Diisoindolomethene Frameworks
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4489
_journal_page_last               4505
_journal_paper_doi               10.1021/jo200246q
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C51 H41 B N2 O2 S2, 0.5(C H2 Cl2), C H4 O'
_chemical_formula_sum            'C52.5 H46 B Cl N2 O3 S2'
_chemical_formula_weight         863.29
_chemical_name_common            'Bodipy-pyrene complex'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                111.176(3)
_cell_angle_beta                 90.737(2)
_cell_angle_gamma                98.606(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0225(6)
_cell_length_b                   12.7998(7)
_cell_length_c                   17.1352(10)
_cell_measurement_reflns_used    4340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.713
_cell_measurement_theta_min      0.998
_cell_volume                     2223.0(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16350
_diffrn_reflns_theta_full        24.80
_diffrn_reflns_theta_max         24.80
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.23
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       prism
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         7519
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0763
_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^)+(0.1649P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2284
_refine_ls_wR_factor_ref         0.2515
_reflns_number_gt                5056
_reflns_number_total             7519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200246q_si_005.cif
_cod_data_source_block           compound_15_squeezed
_cod_database_code               4026355