Enantioselective domino reaction of CO2, amines and allyl chlorides under iridium catalysis: formation of allyl carbamates
Min Zhang; Xiaoming Zhao; Shengcai Zheng; Chem.Commun. 50 (2014) 4455–; doi:10.1039/C4CC00413B

data_7112255
_publ_section_title
;
 Enantioselective domino reaction of CO2, amines and allyl chlorides under
 iridium catalysis: formation of allyl carbamates
;
_journal_name_full               Chem.Commun.
_journal_page_first              4455
_journal_paper_doi               10.1039/C4CC00413B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C13 H16 Br N O2'
_chemical_formula_weight         298.18
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   9.4480(7)
_cell_length_b                   14.9400(10)
_cell_length_c                   28.8691(15)
_cell_measurement_reflns_used    8854
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.06
_cell_volume                     4075.0(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17237
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.990
_diffrn_reflns_theta_min         3.061
_exptl_absorpt_coefficient_mu    4.052
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       rod
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.353
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.199
_refine_ls_abs_structure_details
; 
 Flack x determined using 2421 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.145(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6977
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.1024
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+46.5625P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2680
_refine_ls_wR_factor_ref         0.2743
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                6253
_reflns_number_total             6977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc00413b2.cif
_cod_data_source_block           cu_30926b
_cod_database_code               7112255
_shelx_estimated_absorpt_t_min   0.195
_shelx_estimated_absorpt_t_max   0.793
_shelxl_version_number           2013-2
_shelx_res_checksum              77003
_shelx_hkl_checksum              9948