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_7239362
_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         'C23 H22 N4 O'
_chemical_formula_sum            'C23 H22 N4 O'
_chemical_formula_weight         370.45
_chemical_name_systematic
4-((4-hydroxy-3-(piperidin-1-ylmethyl)naphthalen-1-yl)diazenyl)benzonitrile
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                92.331(10)
_cell_angle_beta                 93.567(10)
_cell_angle_gamma                101.183(10)
_cell_formula_units_Z            2
_cell_length_a                   5.0932(6)
_cell_length_b                   11.5499(14)
_cell_length_c                   16.654(2)
_cell_measurement_reflns_used    11349
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.90
_cell_measurement_theta_min      2.66
_cell_volume                     957.8(2)
_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 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7121
_diffrn_reflns_theta_full        65.67
_diffrn_reflns_theta_max         65.67
_diffrn_reflns_theta_min         2.66
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.9211
_exptl_absorpt_correction_T_min  0.5954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0938P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                2196
_reflns_number_total             2964
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3ra45326j.txt
_cod_data_source_block           CNpip_in_acetone
_cod_database_code               7239362