Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines
De Munck, Lode; Sukowski, Verena; Vila, Carlos; Muñoz, M. Carmen; Pedro, José R.; Organic Chemistry Frontiers 4 (2017) 1624–; doi:10.1039/C7QO00329C

data_1553796
_publ_section_title
;
 Catalytic enantioselective aza-Reformatsky reaction with seven-membered
 cyclic imines dibenzo[b,f][1,4]oxazepines
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1624
_journal_paper_doi               10.1039/C7QO00329C
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H18 Br N O3'
_chemical_formula_weight         412.27
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-01-31 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.537(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4368(4)
_cell_length_b                   6.0294(2)
_cell_length_c                   15.7294(5)
_cell_measurement_reflns_used    5566
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      24.8580
_cell_measurement_theta_min      3.6410
_cell_volume                     943.81(6)
_computing_cell_refinement       'CrysAlisPro 2015'
_computing_data_collection       'CrysAlisPro 2015'
_computing_data_reduction        'CrysAlisPro 2015'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14905
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.837
_diffrn_reflns_theta_min         3.642
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.41q'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4862
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0432P)^2^+0.2194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                4081
_reflns_number_total             4862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00329c2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1553796
_shelx_estimated_absorpt_t_min   0.693
_shelx_estimated_absorpt_t_max   0.810
_shelxl_version_number           2014-1
_shelx_res_checksum              49519
_shelx_hkl_checksum              6707