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_1550701
_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      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 117.882(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6491(7)
_cell_length_b                   12.1125(9)
_cell_length_c                   9.7759(6)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.3255
_cell_measurement_theta_min      2.3880
_cell_volume                     1009.92(12)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.357
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.60
_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            colourless-yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0293P)^2^+0.3375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0650
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4266
_reflns_number_total             4657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc05258a2.cif
_cod_data_source_block           mo_sp17_56_vesely
_cod_database_code               1550701
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.526
_shelx_estimated_absorpt_t_max   0.930
_shelx_res_checksum              99262