Squaramide-catalyzed domino Michael/aza-Henry [3 + 2] cycloaddition: asymmetric synthesis of functionalized 5-trifluoromethyl and 3-nitro substituted pyrrolidines
Liu, Qiang; Zhao, Kun; Zhi, Ying; Raabe, Gerhard; Enders, Dieter; Organic Chemistry Frontiers 4 (2017) 1416–; doi:10.1039/C7QO00161D

data_1553758
_publ_section_title
;
 Squaramide-catalyzed domino Michael/aza-Henry [3 + 2] cycloaddition:
 asymmetric synthesis of functionalized 5-trifluoromethyl and 3-nitro
 substituted pyrrolidines
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1416
_journal_paper_doi               10.1039/C7QO00161D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C17 H18 Br F3 N2 O6'
_chemical_formula_weight         483.27
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_update_record
;
2016-12-22 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   8.3955(2)
_cell_length_b                   14.0900(4)
_cell_length_c                   16.7651(5)
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.84
_cell_measurement_theta_min      4.10
_cell_volume                     1983.19(9)
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_max 67.43
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_detector       'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'micro source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .03
_diffrn_reflns_av_sigmaI/netI    .031
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24836
_diffrn_reflns_theta_max         67.43
_diffrn_reflns_theta_min         4.1
_exptl_absorpt_coefficient_mu    3.43
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       irregular
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         .734
_refine_diff_density_min         -.442
_refine_ls_abs_structure_details 'Flack parameter'
_refine_ls_abs_structure_Flack   0.048(16)
_refine_ls_extinction_coef       831(160)
_refine_ls_extinction_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970'
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   1.002
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .028
_refine_ls_R_factor_gt           .028
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
1/[1.5s^2^(F)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .031
_refine_ls_wR_factor_ref         .031
_reflns_d_resolution_high        .835
_reflns_d_resolution_low         10.763
_reflns_Friedel_coverage         .744
_reflns_limit_h_max              10
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3387
_reflns_number_total             3417
_reflns_threshold_expression     'I > 2.00 sig(I)'
_cod_data_source_file            c7qo00161d2.cif
_cod_data_source_block           gr0838
_cod_original_sg_symbol_Hall     p_2ac_2ab
_cod_original_sg_symbol_H-M      P_21_21_21
_cod_original_formula_sum        'C17 H18 Br1 F3 N2 O6'
_cod_database_code               1553758