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_4116204
_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_formula_analytical     'C14 H12 Cl N O3'
_chemical_formula_sum            'C14 H12 Cl N O3'
_chemical_formula_weight         277.71
_chemical_name_systematic
; 
3-[1-(4-Chlorophanylamino) ethylidene]-6-methyl-3H-pyran-2,4-dione 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                98.525(9)
_cell_angle_beta                 102.805(5)
_cell_angle_gamma                91.989(7)
_cell_formula_units_Z            2
_cell_length_a                   7.3373(5)
_cell_length_b                   8.2919(5)
_cell_length_c                   10.590(9)
_cell_measurement_reflns_used    75
_cell_measurement_temperature    150
_cell_measurement_theta_max      45
_cell_measurement_theta_min      6
_cell_volume                     619.8(5)
_computing_data_reduction        'XTAL3.2 (hall et al., 1994)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      150
_diffrn_measurement_device       'Philips PW1100 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0090
_diffrn_reflns_av_sigmaI/netI    0.0031
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2198
_diffrn_reflns_theta_max         65.08
_diffrn_reflns_theta_min         4.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.772
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0237(17)
_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_all   1.162
_refine_ls_goodness_of_fit_obs   1.164
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_restrained_S_obs      1.164
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_obs          0.0359
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.4555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1074
_refine_ls_wR_factor_obs         0.1074
_reflns_number_observed          2110
_reflns_number_total             2118
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja0009212B_06.cif
_cod_data_source_block           (c')
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.4555P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.4555P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4116204