Pd-catalyzed enantioselective cyclopropanation of nitriles with mono substituted allyl carbonates enabled by the bulky N-heterocyclic carbene ligand
Zhang, Gao-Peng; Huang, Shuai; Jiang, Yang-Jie; Liu, Xiu-Yan; Ding, Chang-Hua; Wei, Yin; Hou, Xue-Long; Chemical Communications  (2019) –; doi:10.1039/C9CC01960J

data_7123483
_publ_section_title
;
 Pd-catalyzed enantioselective cyclopropanation of nitriles with mono
 substituted allyl carbonates enabled by the bulky N-heterocyclic carbene
 ligand
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01960J
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H22 Br N O2 S'
_chemical_formula_weight         408.34
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-07-20 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                85.185(3)
_cell_angle_beta                 81.590(3)
_cell_angle_gamma                82.894(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4750(9)
_cell_length_b                   9.6439(9)
_cell_length_c                   10.8290(10)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.256
_cell_measurement_theta_min      4.374
_cell_volume                     969.16(16)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37202
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.696
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 2498 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         7458
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.2222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5921
_reflns_number_total             7458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01960j2.cif
_cod_data_source_block           mo_d8v18407_0m
_cod_database_code               7123483
_shelx_estimated_absorpt_t_min   0.663
_shelx_estimated_absorpt_t_max   0.760
_shelxl_version_number           2013-4
_shelx_res_checksum              17815
_shelx_hkl_checksum              99991