Isocyanate-, Isothiocyanate-, Urea-, and Thiourea-Substituted Boron Dipyrromethene Dyes as Fluorescent Probes
Raymond Ziessel; Laure Bonardi; Pascal Retailleau; Gilles Ulrich; Journal of Organic Chemistry 71 (2006) 3093–3102; doi:10.1021/jo0600151

data_4021628
_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
;
 Isocyanate-, Isothiocyanate-, Urea-, and Thiourea-Substituted
 Boron Dipyrromethene Dyes as Fluorescent Probes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3093
_journal_page_last               3102
_journal_paper_doi               10.1021/jo0600151
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C23 H25 B F2 N4 O4'
_chemical_formula_sum            'C23 H25 B F2 N4 O4'
_chemical_formula_weight         470.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             10-05-05
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.345(3)
_cell_length_b                   8.431(4)
_cell_length_c                   41.094(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.0
_cell_measurement_theta_min      11.7
_cell_volume                     4624(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.015427
_diffrn_orient_matrix_UB_12      0.033979
_diffrn_orient_matrix_UB_13      -0.021401
_diffrn_orient_matrix_UB_21      0.011558
_diffrn_orient_matrix_UB_22      0.065847
_diffrn_orient_matrix_UB_23      0.011373
_diffrn_orient_matrix_UB_31      0.117057
_diffrn_orient_matrix_UB_32      -0.011000
_diffrn_orient_matrix_UB_33      0.001724
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            7816
_diffrn_reflns_theta_full        67.15
_diffrn_reflns_theta_max         67.15
_diffrn_reflns_theta_min         2.15
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         .228
_refine_diff_density_min         -.277
_refine_diff_density_rms         .047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0814P)^2^+0.9651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                2958
_reflns_number_total             4109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0600151si20060104_094848.cif
_cod_database_code               4021628