Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp<sup>3</sup>)-H Acetalization.
Ye, Baihua; Zhao, Jie; Zhao, Ke; McKenna, Jeffrey M.; Toste, F. Dean; Journal of the American Chemical Society 140 (2018) 8350–8356; doi:10.1021/jacs.8b05962

data_4132743
_publ_section_title
;
 Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective
 \a-C(sp<sup>3</sup>)-H Acetalization.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8350
_journal_page_last               8356
_journal_paper_doi               10.1021/jacs.8b05962
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 I, C50 H56 O4 P, H2 O'
_chemical_formula_sum            'C62 H68 I O5 P'
_chemical_formula_weight         1051.03
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.5441(18)
_cell_length_b                   26.5441(18)
_cell_length_c                   22.7499(17)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.050
_cell_measurement_theta_min      2.480
_cell_volume                     16029.3(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            61389
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.087
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_min         2.348
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  0.4285
_exptl_absorpt_correction_T_min  0.3128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0982 before and 0.0613 after correction. The Ratio of minimum to maximum transmission is 0.7300. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.871
_exptl_crystal_description       block
_exptl_crystal_F_000             4384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.016
_refine_diff_density_min         -0.991
_refine_diff_density_rms         0.183
_refine_ls_abs_structure_details
;
 Flack x determined using 4836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         14197
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0935
_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^)+(0.1650P)^2^+50.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2621
_refine_ls_wR_factor_ref         0.2770
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                12782
_reflns_number_total             14197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05962_si_001.cif
_cod_data_source_block           Compound1
_cod_original_cell_volume        16029(2)
_cod_database_code               4132743
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.876
_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, All O(H,H) groups
2. Restrained distances
 C14-C13 = C15-C13 = C3-C2 = C2-C1 = C12-C10 = C11-C10 = C61-C60 = C62-C61 =
 C58-C57 = C59-C58 = C55-C54 = C56-C54
 1.5 with sigma of 0.02
3. Rigid bond restraints
 C59, C58, C57
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C57, C58, C59
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C59 \\sim C58 \\sim C57: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C1 \\sim C2 \\sim C3: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C57 \\sim C58 \\sim C59: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(C59) \\sim Ueq, Uanis(C57) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5.a Free rotating group:
 O5(H5A,H5B)
5.b Ternary CH refined with riding coordinates:
 C54(H54), C10(H10), C13(H13), C61(H61), C58(H58), C2(H2)
5.c Me refined with riding coordinates:
 C56(H56A,H56B,H56C), C62(H62A,H62B,H62C), C11(H11A,H11B,H11C), C55(H55A,H55B,
 H55C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C60(H60A,H60B,H60C), C15(H15A,
 H15B,H15C), C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C59(H59A,H59B,H59C), C57(H57A,
 H57B,H57C)
5.d Aromatic/amide H refined with riding coordinates:
 C43(H43), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C47(H47),
 C52(H52), C27(H27), C45(H45), C34(H34), C23(H23), C46(H46), C25(H25), C26(H26),
  C50(H50), C44(H44), C30(H30), C36(H36), C37(H37), C24(H24), C9(H9), C35(H35),
 C5(H5)
5.e Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C21)
;
_olex2_submission_special_instructions 'No special instructions were received'