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_7154817
_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         'C20 H16 F3 N1 O2'
_chemical_formula_sum            'C20 H16 F3 N O2'
_chemical_formula_weight         359.34
_chemical_melting_point          369.1(10)
_chemical_name_systematic
(1E,4Z)-1-(9-ethyl-9H-carbazol-3-yl)-6,6,6-trifluoro-5-hydroxyhexa-1,4-dien-3-one
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc11g29w
_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
_audit_creation_date             2013-04-04T14:34:22-00:00
_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                 91.431(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2632(2)
_cell_length_b                   14.5322(4)
_cell_length_c                   16.5698(6)
_cell_measurement_reflns_used    16427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      1.86
_cell_measurement_wavelength     0.71073
_cell_volume                     1748.40(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16427
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+0.4701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.2309
_reflns_number_gt                2462
_reflns_number_total             4436
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ob02295a2.cif
_cod_data_source_block           ad783
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '95-97\%C' was changed to '369.1(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        'C20 H16 F3 N1 O2'
_cod_database_code               7154817