<i>o</i>-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose: <i>o</i>-Azophenylboronic Acids with Inserted Protic Solvent Are the Key Species for a Large Color Change.
Suzuki, Yota; Ikeda, Ayumi; Ohno, Keiji; Fujihara, Takashi; Sugaya, Tomoaki; Ishihara, Koji; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01011

data_4038600
_publ_section_title
;
 <i>o</i>-Azophenylboronic Acid-Based Colorimetric Sensors for d-Fructose:
 <i>o</i>-Azophenylboronic Acids with Inserted Protic Solvent Are the Key
 Species for a Large Color Change.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01011
_journal_year                    2020
_chemical_formula_sum            'C15 H16 B N5 O6'
_chemical_formula_weight         373.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 104.652(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.151(7)
_cell_length_b                   6.869(4)
_cell_length_c                   20.974(11)
_cell_measurement_reflns_used    516
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.16
_cell_measurement_theta_min      2.97
_cell_volume                     1693.7(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1768
_diffrn_reflns_av_unetI/netI     0.2177
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7620
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         1.732
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.2620
_refine_ls_R_factor_gt           0.0900
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0877P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.2432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                947
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            CIF_N5.cif
_cod_data_source_block           DiNitroPh_azoPhB_200
_cod_original_cell_volume        1693.6(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038600
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014-3
_shelx_res_checksum              83853
_shelx_hkl_checksum              69612