Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles
Cristóbal, Christian; Gaviña, Daniel; Alonso, Inés; Ribagorda, María; Carretero, Juan C.; del Pozo, Carlos; Adrio, Javier; Chemical Communications  (2022) –; doi:10.1039/D2CC02902B

data_7130276
_publ_section_title
;
 Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of
 azomethine ylides with fluorinated dipolarophiles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02902B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H12 Cl2 F3 N O3'
_chemical_formula_weight         370.15
_chemical_name_common            JASOdiCl
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.35(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.577(7)
_cell_length_b                   11.122(7)
_cell_length_c                   12.605(8)
_cell_measurement_reflns_used    1507
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      17.8801
_cell_measurement_theta_min      2.5073
_cell_volume                     1531.3(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.1625
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13716
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details
;

Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1828
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0197P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                2310
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02902b2.cif
_cod_data_source_block           03196
_cod_original_cell_volume        1531.3(16)
_cod_database_code               7130276
_shelx_res_checksum              16700
_shelx_hkl_checksum              34254