Regio- and stereoselective synthesis of 5-(trichloromethyl)-isoxazolines
Efimov, Ilya V.; Sokolov, Vladislav A.; Vasilyev, Aleksander V.; Kumar, Yogesh; Khushal,; D’Alterio, Massimo Christian; Talarico, Giovanni; Voskressensky, Leonid G.; New Journal of Chemistry 49 (2025) 17987–17996; doi:10.1039/D5NJ03070F

data_7064016
_publ_section_title
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 Regio- and stereoselective synthesis of 5-(trichloromethyl)-isoxazolines
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17987
_journal_page_last               17996
_journal_paper_doi               10.1039/D5NJ03070F
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C21 H14 Cl3 N O2'
_chemical_formula_sum            'C21 H14 Cl3 N O2'
_chemical_formula_weight         418.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-11 deposited with the CCDC.	2025-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                91.529(4)
_cell_angle_beta                 108.508(4)
_cell_angle_gamma                113.373(4)
_cell_formula_units_Z            4
_cell_length_a                   11.4185(12)
_cell_length_b                   13.3983(14)
_cell_length_c                   14.4111(15)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.26
_cell_volume                     1889.4(4)
_computing_cell_refinement       'SAINT V8.30A (22 Oct 2012)'
_computing_data_reduction        'SAINT V8.30A (22 Oct 2012)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23523
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.514
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1412 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.8390.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0764
_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^)+(0.0546P)^2^+24.1493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2348
_refine_ls_wR_factor_ref         0.2381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6138
_reflns_number_total             7315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03070f2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7064016.cif.'
_cod_original_cell_volume        1889.4(3)
_cod_database_code               7064016
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.848
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C12A(H12A), C13A(H13A), C12B(H12B), C13B(H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C3B(H3B), C4B(H4B),
  C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C11B(H11B), C17B(H17B), C18B(H18B),
 C19B(H19B), C20B(H20B), C21B(H21B)
;
_shelx_res_checksum              62199
_olex2_submission_special_instructions 'No special instructions were received'