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_4514902
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H27 O2 P'
_chemical_formula_sum            'C24 H27 O2 P'
_chemical_formula_weight         378.42
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.18064(10)
_cell_length_b                   15.0632(2)
_cell_length_c                   19.4179(3)
_cell_measurement_reflns_used    6097
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5140
_cell_measurement_theta_min      3.6790
_cell_volume                     2100.31(5)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_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    -66.00  31.00   1.00    1.00    --  -40.98  57.00 150.00   97
  2  \w    -68.00  31.00   1.00    1.00    --  -40.98  57.00  60.00   99
  3  \w     61.00 108.00   1.00    1.00    --  106.95 -94.00 -60.00   47
  4  \w     35.00 121.00   1.00    1.00    --  106.95 -45.00-150.00   86
  5  \w     91.00 133.00   1.00    1.00    --  106.95  45.00  62.00   42
  6  \w    105.00 155.00   1.00    1.00    --  106.95 125.00 -60.00   50
  7  \w     25.00 105.00   1.00    1.00    --  106.95 -94.00-150.00   80
  8  \w     56.00 135.00   1.00    1.00    --  106.95 -61.00 -30.00   79
;
_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      0.1152281000
_diffrn_orient_matrix_UB_12      0.0758517000
_diffrn_orient_matrix_UB_13      -0.0318531000
_diffrn_orient_matrix_UB_21      -0.0244506000
_diffrn_orient_matrix_UB_22      -0.0417542000
_diffrn_orient_matrix_UB_23      -0.0718598000
_diffrn_orient_matrix_UB_31      -0.1793295000
_diffrn_orient_matrix_UB_32      0.0544431000
_diffrn_orient_matrix_UB_33      -0.0107029000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.576
_diffrn_reflns_theta_min         3.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73494
_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    1.197
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0613P)^2^+1.0701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4049
_reflns_number_total             4108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03454_si_004.cif
_cod_data_source_block           74-1
_cod_original_cell_volume        2100.30(5)
_cod_database_code               4514902
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C17(H17), C10(H10), C8(H8), C2(H2A), C16(H16), C9(H9),
 C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              57512
_shelx_hkl_checksum              29877
_olex2_date_sample_data_collection 2019-09-23
_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 1.578
_oxdiff_exptl_absorpt_empirical_full_min 0.581