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_7154819
_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         'C25 H21 B1 F2 O2'
_chemical_formula_sum            'C25 H21 B F2 O2'
_chemical_formula_weight         402.23
_chemical_melting_point          424.1(10)
_chemical_name_systematic
(E)-2,2-difluoro-4-isobutyl-6-(2-(pyren-1-yl)vinyl)-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             2013-10-07T14:33:41-00:00
_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                 117.760(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5387(4)
_cell_length_b                   9.8453(4)
_cell_length_c                   19.8519(9)
_cell_measurement_reflns_used    19127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.022
_cell_measurement_theta_min      2.246
_cell_measurement_wavelength     0.71073
_cell_volume                     1995.65(14)
_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 0.997
_diffrn_measured_fraction_theta_max 0.965
_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  0.0840
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19127
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29.022
_diffrn_reflns_theta_min         2.246
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.47
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2017
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1198P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2477
_reflns_number_gt                2092
_reflns_number_total             5138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02295a2.cif
_cod_data_source_block           ad762
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '150-152\%C' was changed to
'424.1(10)' - 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        'C25 H21 B1 F2 O2'
_cod_database_code               7154819
_audit_block_doi                 10.5517/cc11g2cy