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_7126465
_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         'C17 H13 I O4'
_chemical_formula_sum            'C17 H13 I O4'
_chemical_formula_weight         408.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-26 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                74.922(2)
_cell_angle_beta                 85.722(2)
_cell_angle_gamma                61.931(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5534(3)
_cell_length_b                   9.6302(3)
_cell_length_c                   10.2451(2)
_cell_measurement_reflns_used    9496
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.4640
_cell_measurement_theta_min      4.4100
_cell_volume                     801.80(5)
_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_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_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    -24.00  59.00   0.50    0.17    --   43.80 -55.00  43.00  166
  2  \w     92.00 120.00   0.50    0.69    --  111.75 -55.00  43.00   56
  3  \w     75.00 139.00   0.50    0.69    --  111.75 -77.00  60.00  128
  4  \w     64.00 177.00   0.50    0.69    --  111.75  15.00  30.00  226
  5  \w     94.00 176.00   0.50    0.69    --  111.75  45.00 -90.00  164
  6  \w     95.00 177.00   0.50    0.69    --  111.75  77.00-150.00  164
  7  \w     91.00 176.00   0.50    0.69    --  111.75  55.00-173.00  170
  8  \w     61.00  88.00   0.50    0.17    --   43.80  55.00-173.00   54
  9  \w     24.00  50.00   0.50    0.17    --   43.80  55.00-173.00   52
 10  \w     17.00  58.00   0.50    0.17    --   43.80  77.00 -90.00   82
 11  \w     17.00  61.00   0.50    0.17    --   43.80  78.00-164.72   88
 12  \w      0.00  29.00   0.50    0.17    --  -43.80  55.00-173.00   58
 13  \w    -34.00  -2.00   0.50    0.17    --  -43.80  55.00-173.00   64
 14  \w    -78.00 -21.00   0.50    0.17    --  -43.80 -57.00 -30.00  114
 15  \w    -43.00 -18.00   0.50    0.17    --  -43.80 -77.00 -30.00   50
 16  \w    -52.00 -15.00   0.50    0.17    --  -43.80 -77.00  60.00   74
 17  \w    -61.00 -27.00   0.50    0.17    --  -43.80 -37.00  60.00   68
 18  \w    -68.00 -24.00   0.50    0.17    --  -43.80 -55.00  43.00   88
 19  \w    -66.00 -19.00   0.50    0.17    --  -43.80 -77.00 -60.00   94
 20  \w    -87.00 -61.00   0.50    0.69    --  -90.25 -77.00-150.00   52
 21  \w    -87.00 -60.00   0.50    0.69    --  -90.25 -82.00-151.41   54
 22  \w    -92.00 -61.00   0.50    0.69    --  -90.25 -77.00-110.46   62
 23  \w    -87.00 -61.00   0.50    0.69    --  -90.25 -77.00 -60.00   52
 24  \w    -91.00 -64.00   0.50    0.69    --  -90.25 -77.00   0.00   54
 25  \w    -90.00 -61.00   0.50    0.69    --  -90.25 -77.00  30.00   58
 26  \w    -87.00 -62.00   0.50    0.69    --  -90.25 -74.00  84.53   50
 27  \w    -91.00 -60.00   0.50    0.69    --  -90.25 -79.00 111.17   62
 28  \w   -104.00 -63.00   0.50    0.69    --  -90.25 -75.00  74.77   82
 29  \w    -92.00 -59.00   0.50    0.69    --  -90.25 -81.00  63.03   66
 30  \w    -98.00 -62.00   0.50    0.69    --  -90.25 -74.00 -15.60   72
 31  \w   -106.00 -68.00   0.50    0.69    --  -90.25 -57.00  20.43   76
 32  \w    -98.00 -62.00   0.50    0.69    --  -90.25 -77.00 -30.00   72
 33  \w    -94.00 -62.00   0.50    0.69    --  -90.25 -74.00 -76.74   64
 34  \w   -101.00 -59.00   0.50    0.69    --  -90.25 -81.00-125.94   84
 35  \w   -114.00 -16.00   0.50    0.17    --  -43.80 -19.00-180.00  196
 36  \w    -88.00 -63.00   0.50    0.69    --  -90.25  55.00-173.00   50
 37  \w   -118.00 -15.00   0.50    0.17    --  -43.80 -77.00-180.00  206
 38  \w     31.00  97.00   0.50    0.17    --   43.80-125.00 -90.00  132
 39  \w     39.00  82.00   0.50    0.69    --  111.75 -55.00  43.00   86
 40  \w     39.00 106.00   0.50    0.69    --  111.75 -94.00  30.00  134
 41  \w     39.00 117.00   0.50    0.69    --  111.75-125.00 -60.00  156
 42  \w     41.00 121.00   0.50    0.69    --  111.75-125.00-120.00  160
 43  \w     44.00 103.00   0.50    0.69    --  111.75 -94.00 -30.00  118
 44  \w     89.00 177.00   0.50    0.69    --  111.75  61.00 120.00  176
 45  \w    147.00 174.00   0.50    0.69    --  111.75 125.00 120.00   54
 46  \w    107.00 143.00   0.50    0.69    --  111.75 125.00 120.00   72
 47  \w     86.00 176.00   0.50    0.69    --  111.75  77.00  60.00  180
 48  \w    -95.00 -59.00   0.50    0.69    --  -90.25 -82.00 177.82   72
 49  \w   -101.00 -59.00   0.50    0.69    --  -90.25 -81.00 133.69   84
 50  \w   -114.00 -77.00   0.50    0.17    --  -43.80 -55.00  43.00   74
 51  \w   -111.00 -61.00   0.50    0.69    --  -90.25 -77.00-180.00  100
 52  \w   -109.00 -62.00   0.50    0.69    --  -90.25 -77.00 -90.00   94
 53  \w   -131.00 -68.00   0.50    0.69    --  -90.25 -61.00 -60.00  126
 54  \w   -122.00 -95.00   0.50    0.69    --  -90.25 -77.00-150.00   54
 55  \w   -158.00-132.00   0.50    0.69    --  -90.25 -77.00-110.46   52
 56  \w   -159.00-134.00   0.50    0.69    --  -90.25 -77.00 -90.00   50
 57  \w   -158.00-131.00   0.50    0.69    --  -90.25 -77.00 -30.00   54
 58  \w   -134.00 -64.00   0.50    0.69    --  -90.25 -70.00   0.67  140
 59  \w   -121.00 -64.00   0.50    0.17    --  -43.80 -37.00  60.00  114
 60  \w   -124.00 -61.00   0.50    0.69    --  -90.25 -77.00 150.00  126
 61  \w   -140.00-113.00   0.50    0.69    --  -90.25 -74.00  84.53   54
 62  \w   -140.00-113.00   0.50    0.69    --  -90.25 -77.00  30.00   54
 63  \w   -163.00-113.00   0.50    0.69    --  -90.25 -55.00  43.00  100
 64  \w   -151.00-123.00   0.50    0.69    --  -90.25 -81.00 133.69   56
 65  \w   -162.00-130.00   0.50    0.69    --  -90.25 -75.00  74.77   64
 66  \w   -164.00-108.00   0.50    0.69    --  -90.25 -79.00 111.17  112
 67  \w   -160.00-133.00   0.50    0.69    --  -90.25 -81.00-125.94   54
 68  \w   -163.00-104.00   0.50    0.69    --  -90.25-125.00-180.00  118
 69  \w   -109.00 -16.00   0.50    0.69    --  -90.25  77.00 150.00  186
;
_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      0.1726221000
_diffrn_orient_matrix_UB_12      -0.0663760000
_diffrn_orient_matrix_UB_13      -0.0434945000
_diffrn_orient_matrix_UB_21      0.0402530000
_diffrn_orient_matrix_UB_22      -0.1688262000
_diffrn_orient_matrix_UB_23      0.0942076000
_diffrn_orient_matrix_UB_31      -0.0456662000
_diffrn_orient_matrix_UB_32      -0.0475432000
_diffrn_orient_matrix_UB_33      -0.1164583000
_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     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.634
_diffrn_reflns_theta_min         4.477
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68369
_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    1.691
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.049
_refine_diff_density_min         -1.272
_refine_diff_density_rms         0.095
_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     200
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0607P)^2^+0.8048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3043
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10080f2.cif
_cod_data_source_block           hubu-lyj-tpt-jacs-20190512
_cod_depositor_comments
'Adding full bibliography for 7126465--7126470.cif.'
_cod_original_cell_volume        801.80(4)
_cod_database_code               7126465
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'I C O N H'
_chemical_oxdiff_usercomment     colorless
_shelx_estimated_absorpt_t_max   0.144
_shelx_estimated_absorpt_t_min   0.144
_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.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C8(H8), C4(H4), C9(H9), C1(H1), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              61141
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.664