Evidence for Intramolecular N-H...O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation
Paola Gilli; Valerio Bertolasi; Valeria Ferretti; Gastone Gilli; Journal of the American Chemical Society 122 (2000) 10405–10417; doi:10.1021/ja000921+

data_4116199
_publ_section_title
;
 Evidence for Intramolecular N-H...O Resonance-Assisted Hydrogen Bonding
 in \b-Enaminones and Related Heterodienes. A Combined Crystal-Structural,
 IR and NMR Spectroscopic, and Quantum-Mechanical Investigation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10405
_journal_page_last               10417
_journal_paper_doi               10.1021/ja000921+
_journal_volume                  122
_journal_year                    2000
_chemical_compound_source        ' ......'
_chemical_formula_analytical     'C14 H13 N1 O3'
_chemical_formula_sum            'C14 H13 N O3'
_chemical_formula_weight         243.26
_chemical_name_systematic
;
3-[1-(Phenylamino) ethylidene]-6-methyl-3H-pyran-2,4-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   Fourier
_cell_angle_alpha                90.00(0)
_cell_angle_beta                 91.10(3)
_cell_angle_gamma                90.00(0)
_cell_formula_units_Z            4.00
_cell_length_a                   11.881(1)
_cell_length_b                   7.921(1)
_cell_length_c                   12.893(7)
_cell_measurement_radiation      'Mo K\a'
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_measurement_wavelength     0.71069
_cell_volume                     1213.1(7)
_diffrn_ambient_temperature      295
_diffrn_measurement_device_type  'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3677
_diffrn_reflns_reduction_process ' ......'
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.0944
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3319
_exptl_crystal_description       ' ......'
_exptl_crystal_F_000             512.0
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.02
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2145
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.03
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w= 4F^2^/(\s^2^(I) + (0.04F^2^)^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.060
_reflns_number_gt                2145
_reflns_number_total             3516
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            ja0009212B_01.cif
_cod_data_source_block           (a)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w= 4F^2^/(\s^2^(I) +
(0.04F^2^)^2^)' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w= 4F^2^/(\s^2^(I) + (0.04F^2^)^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'direct methods' was changed to
'direct'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      ' P 1 21/c 1 '
_cod_original_formula_sum        'C14 H13 N1 O3 '
_cod_database_code               4116199