Controlled tautomerism – switching caused by an “underground” anionic effect
Antonov, Liudmil; Deneva, Vera; Kurteva, Vanya; Nedeltcheva, Daniela; Crochet, Aurelien; Fromm, Katharina M.; RSC Advances 3 (2013) 25410–; doi:10.1039/c3ra45326j

data_7239367
_publ_section_title
;
 Controlled tautomerism -- switching caused by an
 &#x201C;underground&#x201D; anionic effect
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              25410
_journal_paper_doi               10.1039/c3ra45326j
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C22 H23 N4 O3, H O4 S'
_chemical_formula_sum            'C22 H24 N4 O7 S'
_chemical_formula_weight         488.51
_chemical_name_systematic
;
1-((4-(2-(4-nitrophenyl)hydrazono)-1-oxo-1,4-dihydronaphthalen-2-yl)
methyl)piperidin-1-ium hydrogensulfate'
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.611(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.498(5)
_cell_length_b                   21.404(5)
_cell_length_c                   13.732(5)
_cell_measurement_reflns_used    15514
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      1.48
_cell_volume                     2202.9(18)
_computing_cell_refinement       X-Area
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28678
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method 'MeOH, H2SO4'
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.42(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         7748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                5188
_reflns_number_total             7748
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3ra45326j.txt
_cod_data_source_block           no2piph2so4
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7239367