1,2-Addition to trifluoromethylated β-enamino diketones: regioselective synthesis of trifluoromethyl-containing azomethine pyrazoles and isoxazoles.
Pianoski, Karlos Eduardo; Poletto, Julia; Vieira da Silva, Michael Jackson; Ascencio Camargo, Jeniffer Nascimento; Jacomini, Andrey Petita; Gonçalves, Davana Silva; Back, Davi Fernando; Moura, Sidnei; Rosa, Fernanda Andreia; Organic & biomolecular chemistry 18 (2020) 2524–2537; doi:10.1039/d0ob00319k

data_7157393
_publ_section_title
;
 1,2-Addition to trifluoromethylated \b-enamino diketones: regioselective
 synthesis of trifluoromethyl-containing azomethine pyrazoles and
 isoxazoles.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2524
_journal_page_last               2537
_journal_paper_doi               10.1039/d0ob00319k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H12 Br F3 N2 O2'
_chemical_formula_sum            'C18 H12 Br F3 N2 O2'
_chemical_formula_weight         425.21
_chemical_melting_point          ?
_chemical_name_common
'trifluormethyl methoxyphenyl iminomethyl bromophenyl isoxal'
_chemical_name_systematic
;
3-trifluormethyl-4-(2-methoxyphenyl)iminomethyl-5-(4-bromophenyl)-isoxal
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2019-10-15T14:35:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-10-15 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.851(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.889(2)
_cell_length_b                   5.2686(10)
_cell_length_c                   25.153(5)
_cell_measurement_reflns_used    3977
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.751
_cell_measurement_theta_min      2.737
_cell_volume                     1692.1(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14746
_diffrn_reflns_theta_full        27.2
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_min         2.74
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_T_max  0.7177
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.8323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                2246
_reflns_number_total             3750
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            d0ob00319k2.cif
_cod_data_source_block           dfbkibri_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157391--7157393.cif.
;
_cod_original_cell_volume        1692.0(5)
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7157393