Synthesis of seven-membered lactones by regioselective and stereoselective iodolactonization of electron-deficient olefins.
Tang, Pan-Ting; Shao, You-Xiang; Wang, Liang-Neng; Wei, Yi; Li, Ming; Zhang, Ni-Juan; Luo, Xiao-Peng; Ke, Zhuofeng; Liu, Yue-Jin; Zeng, Ming-Hua; Chemical communications (Cambridge, England) 56 (2020) 6680–6683; doi:10.1039/c9cc10080f

data_7126467
_publ_section_title
;
 Synthesis of seven-membered lactones by regioselective and
 stereoselective iodolactonization of electron-deficient olefins.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6680
_journal_page_last               6683
_journal_paper_doi               10.1039/c9cc10080f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C19 H15 I O4'
_chemical_formula_sum            'C19 H15 I O4'
_chemical_formula_weight         434.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-31 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.09310(10)
_cell_length_b                   13.1306(2)
_cell_length_c                   15.5266(2)
_cell_measurement_reflns_used    5993
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.7390
_cell_measurement_theta_min      4.4070
_cell_volume                     1642.41(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     22.00  48.00   0.50    0.05    --   43.18  57.00 120.00   52
  2  \w     62.00 114.00   0.50    0.05    --   43.18  57.00 120.00  104
  3  \w     91.00 173.00   0.50    0.06    --  109.88  45.00 -60.00  164
  4  \w    114.00 139.00   0.50    0.06    --  109.88 115.00-157.00   50
  5  \w     97.00 166.00   0.50    0.06    --  109.88 125.00-180.00  138
  6  \w    133.00 159.00   0.50    0.06    --  109.88  45.00-180.00   52
  7  \w     90.00 126.00   0.50    0.06    --  109.88  45.00-180.00   72
  8  \w     88.00 178.00   0.50    0.06    --  109.88  61.00 -90.00  180
  9  \w     85.00 137.00   0.50    0.06    --  109.88 -77.00  90.00  104
 10  \w     83.00 146.00   0.50    0.06    --  109.88-166.00 -33.00  126
 11  \w     34.00  59.00   0.50    0.05    --   43.18-115.00 113.00   50
 12  \w     48.00 109.00   0.50    0.06    --  109.88-115.00 113.00  122
 13  \w     37.00 108.00   0.50    0.06    --  109.88 -94.00 -30.00  142
 14  \w    -93.00 -47.00   0.50    0.05    --  -43.18-166.00 -33.00   92
 15  \w    -64.00 -38.00   0.50    0.06    --  -90.25  61.00  30.00   52
 16  \w    -99.00 -74.00   0.50    0.05    --  -43.18 166.00 -11.00   50
 17  \w    -99.00 -74.00   0.50    0.06    --  -90.25 166.00 -11.00   50
 18  \w    -88.00  -8.00   0.50    0.05    --  -43.18 115.00-157.00  160
 19  \w    -77.00 -52.00   0.50    0.06    --  -90.25 115.00-157.00   50
 20  \w   -109.00 -18.00   0.50    0.05    --  -43.18 -77.00  30.00  182
 21  \w   -139.00 -83.00   0.50    0.06    --  -90.25-115.00 113.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0691118000
_diffrn_orient_matrix_UB_12      -0.1070727000
_diffrn_orient_matrix_UB_13      -0.0225744000
_diffrn_orient_matrix_UB_21      -0.1066144000
_diffrn_orient_matrix_UB_22      0.0442284000
_diffrn_orient_matrix_UB_23      -0.0786396000
_diffrn_orient_matrix_UB_31      0.1428805000
_diffrn_orient_matrix_UB_32      -0.0186191000
_diffrn_orient_matrix_UB_33      -0.0569399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            9809
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.418
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.872
_refine_diff_density_min         -2.405
_refine_diff_density_rms         0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0891P)^2^+1.4317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2753
_reflns_number_total             2932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10080f2.cif
_cod_data_source_block           hubu-lyj-tpt-i
_cod_depositor_comments
'Adding full bibliography for 7126465--7126470.cif.'
_cod_database_code               7126467
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'I C N H O'
_shelx_estimated_absorpt_t_max   0.148
_shelx_estimated_absorpt_t_min   0.148
_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
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              77517
_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 2.759
_oxdiff_exptl_absorpt_empirical_full_min 0.590