Asymmetric cyclopropanation of electron-rich alkenes by the racemic diene rhodium catalyst: the chiral poisoning approach
Trifonova, Evgeniya A.; Ankudinov, Nikita M.; Chusov, Denis; Nelyubina, Yulia V.; Perekalin, Dmitry S.; Chemical Communications  (2022) –; doi:10.1039/D2CC01648F

data_7130074
_publ_section_title
;
 Asymmetric cyclopropanation of electron-rich alkenes by the racemic diene
 rhodium catalyst: the chiral poisoning approach
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01648F
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37
_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-2014/6
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.66(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1340(18)
_cell_length_b                   6.2150(12)
_cell_length_c                   14.976(3)
_cell_measurement_reflns_used    3026
_cell_measurement_temperature    120
_cell_measurement_theta_max      14.85
_cell_measurement_theta_min      2.26
_cell_volume                     814.5(3)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
'MarExperts mardtb goniostat and Rayonix SX 165 detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.745
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8466
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        26.551
_diffrn_reflns_theta_max         31.098
_diffrn_reflns_theta_min         2.467
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5296
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1825 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0790P)^2^+0.0622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                4250
_reflns_number_total             4400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01648f3.cif
_cod_data_source_block           9a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130074
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.964
_shelxl_version_number           2014/6
_shelx_res_checksum              96337