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_4026356
_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
gulrich@chimie.u-strasbg.fr;ziessel@chimie.u-strasbg.fr
_publ_contact_author_fax         0390242635
_publ_contact_author_name
;
Ulrich Gilles;Ziessel Raymond
;
_publ_contact_author_phone       0390242696
_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         'C35 H37 B N2 O2 S2'
_chemical_formula_sum            'C35 H37 B N2 O2 S2'
_chemical_formula_weight         592.60
_chemical_name_systematic
; 
 ? 
;
_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_date             31-08-06
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.34(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.602(3)
_cell_length_b                   22.532(5)
_cell_length_c                   13.602(4)
_cell_measurement_reflns_used    3893
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.967
_cell_measurement_theta_min      0.998
_cell_volume                     3129.6(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21635
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack,(Otwinowski & Minor, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0078(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0843P)^2^+1.6645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                3020
_reflns_number_total             3816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200246q_si_006.cif
_cod_data_source_block           compound_14
_cod_original_cell_volume        3129.6(14)
_cod_database_code               4026356