New conformationally flexible and recyclable aryl iodine catalysts from an inexpensive chiral source for asymmetric oxidations
Zhou, Hai-Jie; Yao, Yi-Ping; Zhang, Tonghui; Chen, Biao; Wang, Xu; Zhao, Hang; Zeng, Jie; Chen, Jian-Ai; Xiao, Xiao; Chen, Fen-Er; Green Chemistry 25 (2023) 10447–10457; doi:10.1039/D3GC02429F

data_7247573
_publ_section_title
;
 New conformationally flexible and recyclable aryl iodine catalysts from
 an inexpensive chiral source for asymmetric oxidations
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              10447
_journal_page_last               10457
_journal_paper_doi               10.1039/D3GC02429F
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C76 H81 I N4 O10 Si2'
_chemical_formula_sum            'C76 H81 I N4 O10 Si2'
_chemical_formula_weight         1393.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-14 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3936(3)
_cell_length_b                   27.4740(6)
_cell_length_c                   9.5840(2)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.59
_cell_volume                     3526.68(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            54725
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.124
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.9103.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1452
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         8123
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.5841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0584
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7539
_reflns_number_total             8123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02429f2.cif
_cod_data_source_block           mo_230104_zhj_mes
_cod_depositor_comments
'Adding full bibliography for 7247573--7247574.cif.'
_cod_database_code               7247573
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Si1-C34 \\sim Si1-C34A
 with sigma of 0.02
 C38-C36 \\sim C38A-C36A
 with sigma of 0.04
 C39-C34 \\sim C39A-C34A
 with sigma of 0.02
 C34-C38 \\sim C34A-C38A
 with sigma of 0.04
 C39-C38 \\sim C39A-C38A
 with sigma of 0.02
 C34-C35 \\sim C34A-C35A
 with sigma of 0.02
 C38-C37 \\sim C38A-C37A
 with sigma of 0.02
 C37-C35 \\sim C37A-C35A
 with sigma of 0.04
 C37-C36 \\sim C37A-C36A
 with sigma of 0.02
 C34-C36 \\sim C34A-C36A
 with sigma of 0.04
 C35-C36 \\sim C35A-C36A
 with sigma of 0.02
 Si1-C39 \\sim Si1-C39A
 with sigma of 0.04
 Si1-C35 \\sim Si1-C35A
 with sigma of 0.04
 C39-C37 \\sim C39A-C37A
 with sigma of 0.04
 C39-C35 \\sim C39A-C35A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Si1 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C34A
\\sim C39A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
4. Others
 Sof(C34A)=Sof(C39A)=Sof(H39A)=Sof(C38A)=Sof(H38A)=Sof(C37A)=Sof(H37A)=
 Sof(C36A)=Sof(H36A)=Sof(C35A)=Sof(H35A)=1-FVAR(1)
 Sof(C34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=Sof(C38)=
 Sof(H38)=Sof(C39)=Sof(H39)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C16(H16),
 C18(H18), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
  C37(H37), C38(H38), C39(H39), C39A(H39A), C38A(H38A), C37A(H37A), C36A(H36A),
 C35A(H35A)
5.d Fitted hexagon refined as free rotating group:
 C34A(C39A,C38A,C37A,C36A,C35A)
5.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              46767
_olex2_submission_special_instructions 'No special instructions were received'