Enantioselective Ring-Opening/Oxidative Phosphorylation and P-Transfer Reaction of Cyclic Diaryliodoniums
Duan, Longhui; Zhao, Kun; Wang, Zhonggui; Zhang, Feng-Lian; Gu, Zhenhua; ACS Catalysis  (2019) 9852–; doi:10.1021/acscatal.9b03454

data_4514901
_publ_section_title
;
 Enantioselective Ring-Opening/Oxidative Phosphorylation and P-Transfer
 Reaction of Cyclic Diaryliodoniums
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9852
_journal_paper_doi               10.1021/acscatal.9b03454
_journal_year                    2019
_chemical_formula_moiety         'C28 H27 O2 P'
_chemical_formula_sum            'C28 H27 O2 P'
_chemical_formula_weight         426.46
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7237(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.27489(12)
_cell_length_b                   7.39505(10)
_cell_length_c                   16.7947(2)
_cell_measurement_reflns_used    6445
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5140
_cell_measurement_theta_min      2.5840
_cell_volume                     1148.01(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     47.00  78.00   1.00    1.00    --   41.11 -99.00-180.00   31
  2  \w     26.00 100.00   1.00    1.00    --  106.95 -95.00 -60.00   74
  3  \w    107.00 135.00   1.00    1.00    --  106.95 -61.00 -60.00   28
  4  \w     88.00 119.00   1.00    1.00    --  106.95 -45.00-150.00   31
  5  \w     84.00 177.00   1.00    1.00    --  106.95  30.00 -90.00   93
  6  \w     53.00  78.00   1.00    1.00    --  106.95 -61.00 -60.00   25
  7  \w     34.00 123.00   1.00    1.00    --  106.95 -30.00  90.00   89
  8  \w    120.00 177.00   1.00    1.00    --  106.95 125.00 150.00   57
  9  \w   -104.00 -23.00   1.00    1.00    --  -41.11 -38.00  30.00   81
 10  \w   -110.00 -17.00   1.00    1.00    --  -41.11 -38.00 -60.00   93
 11  \w    -14.00  30.00   1.00    1.00    --  -41.23  57.00-180.00   44
 12  \w   -100.00 -71.00   1.00    1.00    --  -41.23-148.00 129.00   29
 13  \w    -60.00 -18.00   1.00    1.00    --  -41.23  57.00-180.00   42
 14  \w     42.00  91.00   1.00    1.00    --   41.23-125.00 -30.00   49
 15  \w    151.00 177.00   1.00    1.00    --  106.95  15.00  90.00   26
 16  \w     37.00 138.00   1.00    1.00    --  106.95 -77.00 120.00  101
 17  \w     81.00 134.00   1.00    1.00    --  106.95  30.00   0.00   53
 18  \w     54.00 129.00   1.00    1.00    --  106.95  15.00  90.00   75
 19  \w     76.00 119.00   1.00    1.00    --  106.95-125.00 120.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0614218000
_diffrn_orient_matrix_UB_12      -0.0195856000
_diffrn_orient_matrix_UB_13      0.0820426000
_diffrn_orient_matrix_UB_21      -0.1548663000
_diffrn_orient_matrix_UB_22      0.0016607000
_diffrn_orient_matrix_UB_23      -0.0409596000
_diffrn_orient_matrix_UB_31      0.0045721000
_diffrn_orient_matrix_UB_32      -0.2073835000
_diffrn_orient_matrix_UB_33      -0.0080275000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7337
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.634
_diffrn_reflns_theta_min         2.640
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1235 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0529P)^2^+0.1764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.513
_reflns_Friedel_fraction_full    0.631
_reflns_Friedel_fraction_max     0.590
_reflns_number_gt                3675
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03454_si_003.cif
_cod_data_source_block           dlh-5-109
_cod_original_cell_volume        1148.00(3)
_cod_database_code               4514901
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C11(H11), C18(H18), C2(H2), C20(H20), C21(H21), C14(H14), C10(H10),
 C3(H3), C23(H23), C4(H4), C24(H24), C15(H15), C9(H9)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C25(H25A,H25B,
 H25C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.562