Proline Bulky Substituents Consecutively Act as Steric Hindrances and Directing Groups in a Michael/Conia-Ene Cascade Reaction under Synergistic Catalysis
Putatunda, Salil; Alegre-Requena, Juan V; Meazza, Marta; Franc, Michael; Rohalova, Dominika; Vemuri, Pooja Y.; Císařová, Ivana; Herrera, Raquel P.; Rios, Ramon; Vesely, Jan; Chemical Science  (2019) –; doi:10.1039/C8SC05258A

data_1550702
_publ_section_title
;
 Proline Bulky Substituents Consecutively Act as Steric Hindrances and
 Directing Groups in a Michael/Conia-Ene Cascade Reaction under
 Synergistic Catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05258A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C22 H19 Br N2 O3'
_chemical_formula_sum            'C22 H19 Br N2 O3'
_chemical_formula_weight         439.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-07-29 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3176(3)
_cell_length_b                   10.5583(3)
_cell_length_c                   18.2395(5)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4783
_cell_measurement_theta_min      2.2288
_cell_volume                     1986.94(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.229
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  0.70
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.3255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0561
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4322
_reflns_number_total             4570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05258a2.cif
_cod_data_source_block           mo_sp17_57_vesely
_cod_database_code               1550702
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.592
_shelx_estimated_absorpt_t_max   0.699
_shelx_res_checksum              46622