Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies.
Stark, Daniel G.; Williamson, Patrick; Gayner, Emma R.; Musolino, Stefania F.; Kerr, Ryan W. F.; Taylor, James E.; Slawin, Alexandra M. Z.; O'Riordan, Timothy J C; Macgregor, Stuart A.; Smith, Andrew D.; Organic & biomolecular chemistry 14 (2016) 8957–8965; doi:10.1039/c6ob01557c

data_7155211
_publ_section_title
;
 Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic
 and computational studies.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8957
_journal_page_last               8965
_journal_paper_doi               10.1039/c6ob01557c
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Br N O3'
_chemical_formula_sum            'C17 H16 Br N O3'
_chemical_formula_weight         362.22
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-29
_audit_creation_method           'by CrystalStructure 4.1'
_audit_update_record
;
2016-06-06 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.5275(14)
_cell_length_b                   13.374(3)
_cell_length_c                   15.278(3)
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.00
_cell_volume                     1538.1(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7486
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_min         2.024
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.692
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.47
_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   0.003(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0314P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                2251
_reflns_number_total             2746
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6ob01557c3.cif
_cod_data_source_block           23
_cod_depositor_comments          'Adding full bibliography for 7155211.cif.'
_cod_database_code               7155211
_shelx_res_checksum              32265