Enantioselective Organocatalytic Amine-Isocyanate Capture-Cyclization: Regioselective Alkene Iodoamination for the Synthesis of Chiral Cyclic Ureas.
Struble, Thomas J.; Lankswert, Hannah M.; Pink, Maren; Johnston, Jeffrey N.; ACS catalysis 8 (2018) 11926–11931; doi:10.1021/acscatal.8b03708

data_4515776
_publ_section_title
;
 Enantioselective Organocatalytic Amine-Isocyanate Capture-Cyclization:
 Regioselective Alkene Iodoamination for the Synthesis of Chiral Cyclic
 Ureas.
;
_journal_issue                   12
_journal_name_full               'ACS catalysis'
_journal_page_first              11926
_journal_page_last               11931
_journal_paper_doi               10.1021/acscatal.8b03708
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 Br I N2 O4 S'
_chemical_formula_sum            'C24 H22 Br I N2 O4 S'
_chemical_formula_weight         641.30
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4546(12)
_cell_length_b                   13.367(2)
_cell_length_c                   24.063(4)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.86
_cell_volume                     2397.8(7)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_collection       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2013)'
_computing_publication_material  'SHELXTL (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 83.33
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
'0.50 degree frames measured for 10 seconds each'
_diffrn_measurement_device       'APEX Kappa Duo'
_diffrn_measurement_device_type  Kappa
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22668
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         1.743
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2014'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 2015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0344P)^2^+0.0995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0694
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                5092
_reflns_number_total             5492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03708_si_003.cif
_cod_data_source_block           16055
_cod_original_cell_volume        2397.7(7)
_cod_database_code               4515776
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.444
_shelx_estimated_absorpt_t_max   0.859
_shelx_res_checksum              66342
_shelx_hkl_checksum              32496