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_7130073
_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 ad
_chemical_formula_moiety         'C29 H32 F4 N O2 Rh S'
_chemical_formula_sum            'C29 H32 F4 N O2 Rh S'
_chemical_formula_weight         637.52
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8702(10)
_cell_length_b                   14.0428(12)
_cell_length_c                   18.3564(16)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.37
_cell_volume                     2802.1(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_min         1.826
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1494 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.8081.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0304P)^2^+0.2673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6433
_reflns_number_total             6771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01648f3.cif
_cod_data_source_block           2c
_cod_database_code               7130073
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.782
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C13(H13), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              69077
_olex2_submission_special_instructions 'No special instructions were received'