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_4026352
_publ_contact_author_address
;
Laboratoire de Chimie
Universit\'e Louis Pasteur, d'Electronique et de Photonique Moleculaires
ECPM, 1 rue Blaise Pascal
Strasbourg
F-67008
FRANCE
;
_publ_contact_author_email       ZIESSEL@CHIMIE.U-STRASBG.FR
_publ_contact_author_fax         0390241232
_publ_contact_author_name        'Raymond Ziessel'
_publ_contact_author_phone       0390241593
_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         'C49 H41 B N2 O2 S2'
_chemical_formula_sum            'C49 H41 B N2 O2 S2'
_chemical_formula_weight         764.77
_chemical_name_systematic
; 
 ? 
;
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
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_atom_sites_solution_secondary   difmap
_audit_creation_date             01-01-05
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.988(3)
_cell_angle_beta                 67.773(4)
_cell_angle_gamma                67.228(4)
_cell_formula_units_Z            2
_cell_length_a                   12.2879(7)
_cell_length_b                   13.5015(10)
_cell_length_c                   14.9489(12)
_cell_measurement_reflns_used    3523
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.980
_cell_measurement_theta_min      0.998
_cell_volume                     2039.7(3)
_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 .994
_diffrn_measured_fraction_theta_max .994
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12015
_diffrn_reflns_theta_full        20.09
_diffrn_reflns_theta_max         20.09
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .210
_refine_diff_density_min         -.242
_refine_diff_density_rms         .032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         3833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.8052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                2882
_reflns_number_total             3833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200246q_si_002.cif
_cod_data_source_block           sg196f1
_cod_database_code               4026352