Copper-catalyzed enantioselective propargylic [3 + 2] cycloaddition: access to oxygen heterocycles featuring a CF<sub>3</sub>-substituted quaternary stereocenter.
Rohilla, Shweta; Khan, Zahid Ahmad; Singh, Vinod K.; Organic & biomolecular chemistry 23 (2025) 2731–2736; doi:10.1039/d4ob02043j

data_7160387
_publ_section_title
;
 Copper-catalyzed enantioselective propargylic [3 + 2] cycloaddition:
 access to oxygen heterocycles featuring a CF<sub>3</sub>-substituted
 quaternary stereocenter.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2731
_journal_page_last               2736
_journal_paper_doi               10.1039/d4ob02043j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H12 Br F3 N2 O3'
_chemical_formula_sum            'C16 H12 Br F3 N2 O3'
_chemical_formula_weight         417.19
_chemical_name_systematic        shweta
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.4398(3)
_cell_length_b                   10.4398(3)
_cell_length_c                   28.3533(9)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.42
_cell_volume                     3090.21(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            64032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.423
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4663
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0822 after correction.
The Ratio of minimum to maximum transmission is 0.6254.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_description       cube
_exptl_crystal_F_000             1664
_exptl_crystal_preparation       'pentane slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_refine_diff_density_max         0.500
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 3092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.053(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7099
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0407P)^2^+2.5701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6762
_reflns_number_total             7099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02043j2.cif
_cod_data_source_block           8febb_0m
_cod_depositor_comments
'Adding full bibliography for 7160387--7160388.cif.'
_cod_original_cell_volume        3090.2(2)
_cod_database_code               7160387
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00Q(H00Q), C00V(H00V), C00X(H00X), C010(H010), C013(H013),
 C016(H016), C01A(H01D)
1.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00Z(H00D,H00E,H00F), C019(H01A,H01B,H01C), C01B(H01E,
 H01F,H01G)
1.c Idealised tetrahedral OH refined as rotating group:
 C20(H20A), C01D(H01H)
;
_shelx_res_checksum              29897
_olex2_submission_special_instructions 'No special instructions were received'