Asymmetric synthesis of dihydro-1,3-dioxepines by Rh(II)/Sm(III) relay catalytic three-component tandem [4+3]-cycloaddition
Xu, Chaoran; Qiao, Jianglin; Dong, Shunxi; Zhou, Yuqiao; Liu, Xiaohua; Feng, Xiaoming; Chemical Science  (2021) –; doi:10.1039/D1SC01019K

data_1560951
_publ_section_title
;
 Asymmetric synthesis of dihydro-1,3-dioxepines by Rh(II)/Sm(III) relay
 catalytic three-component tandem [4+3]-cycloaddition
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01019K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H58 N4 O4 Sm, 3(C F3 O3 S), 2(C2 H5 O)'
_chemical_formula_sum            'C88 H136 F18 N8 O30 S6 Sm2'
_chemical_formula_weight         2621.10
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-02 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.980(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.6883(9)
_cell_length_b                   20.9229(13)
_cell_length_c                   21.4877(13)
_cell_measurement_reflns_used    9577
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.48
_cell_volume                     5971.8(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      148(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            268014
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         2.381
_exptl_absorpt_coefficient_mu    1.177
_exptl_absorpt_correction_T_max  0.8883
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       flake
_exptl_crystal_F_000             2684
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH, Ether'
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 9611 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.0089(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1461
_refine_ls_number_reflns         21553
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+1.3101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0495
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                20675
_reflns_number_total             21553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01019k2.cif
_cod_data_source_block           ktf011
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1560951
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.847
_shelx_res_checksum              68930
_shelx_hkl_checksum              96333
_shelx_fab_checksum              64083