The Nature of Solid-State N-H...O/O-H...N Tautomeric Competition in Resonant Systems. Intramolecular Proton Transfer in Low-Barrier Hydrogen Bonds Formed by the ...OC-CN-NH... <‒> ...HO-CC-NN... Ketohydrazone-Azoenol System. A Variable-Temperature X-ray Crystallographic and DFT Computational Study
Paola Gilli; Valerio Bertolasi; Loretta Pretto; Antonín Lyčka; Gastone Gilli; Journal of the American Chemical Society 124 (2002) 13554–13567; doi:10.1021/ja020589x

data_4115264
_publ_section_title
;
 The Nature of Solid-State N-H...O/O-H...N Tautomeric Competition in
 Resonant Systems. Intramolecular Proton Transfer in Low-Barrier Hydrogen
 Bonds Formed by the ...OC-CN-NH... <--> ...HO-CC-NN...
 Ketohydrazone-Azoenol System. A Variable-Temperature X-ray
 Crystallographic and DFT Computational Study
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13554
_journal_page_last               13567
_journal_paper_doi               10.1021/ja020589x
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C16 H11 F N2 O'
_chemical_formula_sum            'C16 H11 F N2 O'
_chemical_formula_weight         266.27
_chemical_name_systematic
;
(1Z)-naphthalene-1,2-dione 1-[(2-fluorophenyl)hydrazone]
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.7800(10)
_cell_length_b                   7.2962(4)
_cell_length_c                   7.3283(5)
_cell_measurement_reflns_used    5993
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.92
_cell_volume                     1271.49(12)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa CCd server software (Nonius, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP II (Johnson, 1976)'
_computing_publication_material
;
  SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '\f scans and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5993
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0319P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                1847
_reflns_number_total             2169
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ja020589x_8.cif
_cod_data_source_block           oF(295K)
_cod_database_code               4115264