Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO<sub>2</sub>-Capture: Discovery, Development, and Mechanism.
Yousefi, Roozbeh; Struble, Thomas J.; Payne, Jenna L.; Vishe, Mahesh; Schley, Nathan D.; Johnston, Jeffrey N.; Journal of the American Chemical Society 141 (2019) 618–625; doi:10.1021/jacs.8b11793

data_4133619
_publ_section_title
;
 Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl
 Amines by CO<sub>2</sub>-Capture: Discovery, Development, and Mechanism.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              618
_journal_page_last               625
_journal_paper_doi               10.1021/jacs.8b11793
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 F3 I N O2'
_chemical_formula_sum            'C19 H17 F3 I N O2'
_chemical_formula_weight         475.24
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_audit_update_record
;
2015-07-13 # Formatted by publCIF

;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8606(4)
_cell_length_b                   9.1352(4)
_cell_length_c                   25.0134(12)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.76
_cell_volume                     1796.17(15)
_computing_cell_refinement       'APEX II v2010.11.3 (Bruker, 2013)'
_computing_data_collection       'APEX II v2010.11.3 (Bruker, 2013)'
_computing_data_reduction        'APEX II v2010.11.3 (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2013)'
_computing_publication_material  'SHELXTL (Bruker, 2013)'
_computing_structure_refinement  'SHELXTL (Bruker, 2012)'
_computing_structure_solution    'SHELXTL (Bruker, 2013)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            37866
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  0.7973
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G Sheldrick; 2012'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.4853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0468
_reflns_number_gt                5217
_reflns_number_total             5251
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {3ff15624-dc66-4c44-9cdd-1fa35bc878cf}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            ja8b11793_si_003.cif
_cod_data_source_block           14048
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4133619