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_1560947
_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         'C28 H25 Br O6'
_chemical_formula_sum            'C28 H25 Br O6'
_chemical_formula_weight         537.39
_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_method           SHELXL-2018/3
_audit_update_record
;
2020-07-11 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6194(5)
_cell_length_b                   15.9110(9)
_cell_length_c                   16.4920(9)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.84
_cell_measurement_theta_min      2.47
_cell_volume                     2524.2(2)
_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      170(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            115413
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.138
_diffrn_reflns_theta_min         2.474
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_max  0.7116
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.455
_exptl_crystal_size_min          0.272
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
; 
 Flack x determined using 3157 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.011(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         9563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0192P)^2^+0.7606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                8101
_reflns_number_total             9563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01019k2.cif
_cod_data_source_block           zhy006
_cod_database_code               1560947
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.660
_shelx_res_checksum              4488
_shelx_hkl_checksum              2490