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_7249246
_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         'C19 H14 F5 N O2'
_chemical_formula_sum            'C19 H14 F5 N O2'
_chemical_formula_weight         383.32
_chemical_name_systematic
6,6-difluoro-4-(4-methoxyphenyl)-5-(p-tolyl)-2-(trifluoromethyl)-6H-1,3-oxazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7156(7)
_cell_length_b                   8.5123(3)
_cell_length_c                   21.5158(9)
_cell_measurement_reflns_used    9323
_cell_measurement_temperature    180
_cell_measurement_theta_max      72.2033
_cell_measurement_theta_min      4.1094
_cell_volume                     3427.7(2)
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.047
_diffrn_reflns_av_unetI/netI     0.071
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            46820
_diffrn_reflns_theta_full        72.321
_diffrn_reflns_theta_max         72.321
_diffrn_reflns_theta_min         4.109
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.44
_refine_ls_extinction_coef       64(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.0004765
_refine_ls_shift/su_mean         0.0000679
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.96P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1099
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1098
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2934
_reflns_number_total             3381
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.12
_oxford_diffrn_Wilson_scale      68.56
_oxford_refine_ls_scale          0.12223(7)
_cod_data_source_file            d4ra04794j2.cif
_cod_data_source_block           I
_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_database_code               7249246
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0451
_reflns_number_all               3381