Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine
Payne, Jenna L.; Deng, Zihang; Flach, Andrew L.; Johnston, Jeffrey N.; Chemical Science 13 (2022) 7318–7324; doi:10.1039/D2SC01587K

data_1567088
_publ_section_title
;
 Enantioselective iodolactonization to prepare \e-lactone rings using
 hypervalent iodine
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              7318
_journal_page_last               7324
_journal_paper_doi               10.1039/D2SC01587K
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H14 Cl I O2'
_chemical_formula_sum            'C13 H14 Cl I O2'
_chemical_formula_weight         364.59
_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_date             2021-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2022-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9639(3)
_cell_length_b                   11.1228(3)
_cell_length_c                   13.2590(4)
_cell_measurement_reflns_used    6156
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.9060
_cell_measurement_theta_min      3.0720
_cell_volume                     1321.97(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_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 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_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    -42.00   8.00   1.00   12.00    --  -19.12 -77.00 -30.00   50
  2  \w    -48.00  36.00   1.00   12.00    --   19.27 -57.00 -60.00   84
  3  \w    -50.00  89.00   1.00   12.00    --   19.27   0.00 -90.00  139
  4  \w    -42.00   8.00   1.00   12.00    --  -19.12 -77.00-120.00   50
  5  \w      3.00  56.00   1.00   12.00    --   19.27  57.00  90.00   53
  6  \w     39.00  91.00   1.00   12.00    --   19.27 178.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0433870000
_diffrn_orient_matrix_UB_12      0.0496201000
_diffrn_orient_matrix_UB_13      -0.0165327000
_diffrn_orient_matrix_UB_21      0.0584108000
_diffrn_orient_matrix_UB_22      -0.0176347000
_diffrn_orient_matrix_UB_23      0.0328924000
_diffrn_orient_matrix_UB_31      0.0309474000
_diffrn_orient_matrix_UB_32      -0.0360736000
_diffrn_orient_matrix_UB_33      -0.0387988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.620
_diffrn_reflns_theta_min         2.390
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.832
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details
;
 Flack x determined using 1306 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+0.5157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                3467
_reflns_number_total             3681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01587k3.cif
_cod_data_source_block           zd-2-227_auto
_cod_depositor_comments          'Adding full bibliography for 1567088.cif.'
_cod_database_code               1567088
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C13H14ClIO2
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
;
_shelx_res_checksum              7693
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.478