Torsionally Responsive C3-Symmetric Azo Dyes: Azo-Hydrazone Tautomerism, Conformational Switching, and Application for Chemical Sensing
Ho Yong Lee; Xinli Song; Hyunsoo Park; Mu-Hyun Baik; Dongwhan Lee; Journal of the American Chemical Society 132 (2010) 12133–12144; doi:10.1021/ja105121z

data_4102968
_publ_section_title
;
 Torsionally Responsive C3-Symmetric Azo Dyes: Azo-Hydrazone Tautomerism,
 Conformational Switching, and Application for Chemical Sensing
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12133
_journal_page_last               12144
_journal_paper_doi               10.1021/ja105121z
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C66 H78 N6 O9, C2 H3 N'
_chemical_formula_sum            'C68 H81 N7 O9'
_chemical_formula_weight         1140.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.6650(10)
_cell_angle_beta                 105.0540(10)
_cell_angle_gamma                111.7840(10)
_cell_formula_units_Z            2
_cell_length_a                   14.8322(5)
_cell_length_b                   15.7438(6)
_cell_length_c                   16.0370(10)
_cell_measurement_reflns_used    2509
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      15.99
_cell_measurement_theta_min      0.81
_cell_volume                     3188.4(3)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    'Diamond 3.2'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  'diamond 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            81234
_diffrn_reflns_theta_full        15.99
_diffrn_reflns_theta_max         15.99
_diffrn_reflns_theta_min         0.81
_diffrn_source                   synchrotron
_diffrn_source_type              'APS 15-ID'
_exptl_absorpt_coefficient_mu    0.050
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (R. Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.080
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         15449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+2.0681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2192
_reflns_number_gt                10427
_reflns_number_total             15449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105121z_si_002.cif
_cod_data_source_block           hydrz
_cod_database_code               4102968