Pd-Catalyzed Asymmetric Cyclopropanation Reaction of Acyclic Amides with Allyl and Polyenyl Carbonates. Experimental and Computational Studies for the Origin of Cyclopropane Formation
Huang, Jian-Qiang; Liu, Wei; Zheng, Bao-Hui; Liu, Xiu Yan; Yang, Zhen; Ding, Chang-Hua; Li, Hao; Peng, Qian; Hou, Xue-Long; ACS Catalysis 8 (2018) 1964–; doi:10.1021/acscatal.7b03744

data_4514387
_publ_section_title
;
 Pd-Catalyzed Asymmetric Cyclopropanation Reaction of Acyclic Amides with
 Allyl and Polyenyl Carbonates. Experimental and Computational Studies for
 the Origin of Cyclopropane Formation
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1964
_journal_paper_doi               10.1021/acscatal.7b03744
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H24 Br N O'
_chemical_formula_weight         446.37
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.875(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.693(4)
_cell_length_b                   6.314(2)
_cell_length_c                   15.570(5)
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.705
_cell_measurement_theta_min      4.978
_cell_volume                     1116.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6405
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2158
_reflns_number_total             3567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs7b03744_si_002.cif
_cod_data_source_block           cd212102
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4514387--4514388.cif.
;
_cod_original_cell_volume        1116.1(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4514387