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_7126468
_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 H17 I O5'
_chemical_formula_sum            'C19 H17 I O5'
_chemical_formula_weight         452.22
_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             2019-06-14
_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                111.642(2)
_cell_angle_beta                 106.312(2)
_cell_angle_gamma                106.245(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8357(2)
_cell_length_b                   10.4353(3)
_cell_length_c                   10.4634(3)
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      30.0630
_cell_measurement_theta_min      2.3080
_cell_volume                     865.10(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_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 0.842
_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     -3.00  31.00   0.50    0.53    --   10.30 -57.00 -30.00   68
  2  \w     -5.00  21.00   0.50    0.53    --   10.30 -99.00 -30.00   52
  3  \w    -14.00  30.00   0.50    0.53    --   -9.20 -99.00 -90.00   88
  4  \w     22.00  48.00   0.50    0.53    --   10.30-104.00-179.00   52
  5  \w    -17.00   9.00   0.50    0.53    --   -9.20 -99.00 -30.00   52
  6  \w    -26.00   6.00   0.50    0.53    --   -9.20 -99.00  60.00   64
  7  \w    -25.00  48.00   0.50    0.53    --   10.30 -99.00 120.00  146
  8  \w    -64.00 -31.00   0.50    0.53    --   10.30 -57.00 -30.00   66
  9  \w     -3.00  22.00   0.50    0.53    --   -9.20 -19.00 -30.00   50
 10  \w     38.00  64.00   0.50    0.53    --   -9.20  57.00-180.00   52
 11  \w    -23.00  10.00   0.50    0.53    --   -9.20  57.00-180.00   66
 12  \w    -85.00 -39.00   0.50    0.53    --   -9.20 -19.00 -30.00   92
 13  \w    -60.00 -25.00   0.50    0.53    --   10.30 -57.00   0.00   70
 14  \w    -64.00  29.00   0.50    0.53    --   10.30 -57.00-120.00  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      -0.0108288000
_diffrn_orient_matrix_UB_12      -0.0768852000
_diffrn_orient_matrix_UB_13      -0.0268588000
_diffrn_orient_matrix_UB_21      0.0352445000
_diffrn_orient_matrix_UB_22      0.0148909000
_diffrn_orient_matrix_UB_23      0.0761901000
_diffrn_orient_matrix_UB_31      -0.0745981000
_diffrn_orient_matrix_UB_32      -0.0206194000
_diffrn_orient_matrix_UB_33      0.0011126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.126
_diffrn_reflns_theta_min         2.320
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17551
_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    1.736
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.876
_refine_diff_density_min         -1.700
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0425P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3978
_reflns_number_total             4297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10080f2.cif
_cod_data_source_block           tpt-9-7
_cod_depositor_comments
'Adding full bibliography for 7126465--7126470.cif.'
_cod_original_cell_volume        865.10(4)
_cod_database_code               7126468
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.705
_shelx_estimated_absorpt_t_min   0.705
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_res_checksum              30636
_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 2.219
_oxdiff_exptl_absorpt_empirical_full_min 0.517