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_4515777
_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         'C26 H25 I N2 O4 S'
_chemical_formula_sum            'C26 H25 I N2 O4 S'
_chemical_formula_weight         588.44
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.7165(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8374(3)
_cell_length_b                   14.8665(6)
_cell_length_c                   12.6176(6)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.17
_cell_volume                     1234.61(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
'0.50 degree frames measured for 20 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  0.0321
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25107
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.103
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.417
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2014'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 3152 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         7073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0200
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+0.1906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0527
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                6970
_reflns_number_total             7073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03708_si_004.cif
_cod_data_source_block           16052
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4515777
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.660
_shelx_estimated_absorpt_t_max   0.736
_shelx_res_checksum              43012
_shelx_hkl_checksum              65726