Borondifluoride complexes of hemicurcuminoids as bio-inspired push-pull dyes for bioimaging.
Kim, Eunsun; Felouat, Abdellah; Zaborova, Elena; Ribierre, Jean-Charles; Wu, Jeong Weon; Senatore, Sébastien; Matthews, Cédric; Lenne, Pierre-François; Baffert, Carole; Karapetyan, Artak; Giorgi, Michel; Jacquemin, Denis; Ponce-Vargas, Miguel; Guennic, Boris Le; Fages, Frédéric; D'Aléo, Anthony; Organic & biomolecular chemistry 14 (2016) 1311–1324; doi:10.1039/c5ob02295a

data_7154821
_publ_section_title
;
 Borondifluoride complexes of hemicurcuminoids as bio-inspired push-pull
 dyes for bioimaging.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1311
_journal_page_last               1324
_journal_paper_doi               10.1039/c5ob02295a
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H15 B1 F2 O2 S1'
_chemical_formula_sum            'C18 H15 B F2 O2 S'
_chemical_formula_weight         344.17
_chemical_melting_point          536.6(15)
_chemical_name_systematic
(E)-2,2-difluoro-6-(4-(methylthio)styryl)-4-phenyl-2H-1,3,2-dioxaborinin-1-ium-2-uide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2013-10-01T16:13:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.565(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0580(2)
_cell_length_b                   11.8497(3)
_cell_length_c                   17.4330(5)
_cell_measurement_reflns_used    15748
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.013
_cell_measurement_theta_min      3.106
_cell_measurement_wavelength     0.71073
_cell_volume                     1611.09(7)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15748
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29.013
_diffrn_reflns_theta_min         3.106
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.5137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                2616
_reflns_number_total             4145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02295a2.cif
_cod_data_source_block           ad741
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '262-265\%C' was changed to
'536.6(15)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154817--7154821.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C18 H15 B1 F2 O2 S1'
_cod_database_code               7154821
_audit_block_doi                 10.5517/cc1k232t