Transformation of 5-acylated <i>N</i>-fluoroalkyl-1,2,3-triazoles to trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and 1,3-oxazin-6-ones <i>via</i> ketenimines.
Janecký, Lukáš; Klepetářová, Blanka; Beier, Petr; RSC advances 14 (2024) 26938–26942; doi:10.1039/d4ra04794j

data_7249248
_publ_section_title
;
 Transformation of 5-acylated <i>N</i>-fluoroalkyl-1,2,3-triazoles to
 trifluoromethylated ring-fused isoquinolines, 1,3-oxazines, and
 1,3-oxazin-6-ones <i>via</i> ketenimines.
;
_journal_issue                   37
_journal_name_full               'RSC advances'
_journal_page_first              26938
_journal_page_last               26942
_journal_paper_doi               10.1039/d4ra04794j
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H8 F3 N O2 S'
_chemical_formula_sum            'C15 H8 F3 N O2 S'
_chemical_formula_weight         323.29
_chemical_name_systematic
5-phenyl-4-(thiophen-2-yl)-2-(trifluoromethyl)-6H-1,3-oxazin-6-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.1605(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2617(4)
_cell_length_b                   14.3039(5)
_cell_length_c                   9.1250(3)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    180
_cell_measurement_theta_max      70.0287
_cell_measurement_theta_min      4.1558
_cell_volume                     1388.48(8)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_unetI/netI     0.048
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            32093
_diffrn_reflns_theta_full        70.075
_diffrn_reflns_theta_max         70.075
_diffrn_reflns_theta_min         4.156
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.516
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9336
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.0004784
_refine_ls_shift/su_mean         0.0000485
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.55P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0738
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0738
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2497
_reflns_number_total             2637
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.37
_oxford_diffrn_Wilson_scale      26.91
_oxford_refine_ls_scale          0.20519(14)
_cod_data_source_file            d4ra04794j2.cif
_cod_data_source_block           I_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249248
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0298
_reflns_number_all               2637