Exploiting Intramolecular Hydrogen Bond for Highly (Z)-Selective & Metal Free Synthesis of Amide Substituted β-aminoenones
Subramaniam, Palaniraja; Ramasubbu, Chandrasekaran; Athiramu, Selvaraj; Green Chem.  (2017) –; doi:10.1039/C7GC00909G

data_7228229
_publ_section_title
;
 Exploiting Intramolecular Hydrogen Bond for Highly (Z)-Selective &amp;
 Metal Free Synthesis of Amide Substituted \b-aminoenones
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC00909G
_journal_year                    2017
_chemical_formula_sum            'C12 H11 F3 N2 O2'
_chemical_formula_weight         272.23
_chemical_melting_point          493.9(3)
_chemical_name_common
(Z)-2-(aminomethylene)-3-oxo-N-(4-(trifluoromethyl)phenyl)butanamide
_chemical_name_systematic
(2Z)-2-(aminomethylidene)-3-oxo-N-[4-(trifluoromethyl)phenyl]butanamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-04 deposited with the CCDC.
2017-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.918(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1752(11)
_cell_length_b                   13.714(2)
_cell_length_c                   12.346(2)
_cell_measurement_reflns_used    2641
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.58
_cell_measurement_theta_min      3.2
_cell_volume                     1214.2(3)
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13410
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.220
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.9021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+2.0296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1396
_reflns_number_total             2383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc00909g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '493.65-494.25' was changed to
'493.9(3)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1214.1(3)
_cod_database_code               7228229
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              9322
_solvent_exptl_crystal_recrystallization_method Ethanol