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_7126469
_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_absolute_configuration S
_chemical_formula_moiety         'C19 H14 F3 I O4'
_chemical_formula_sum            'C19 H14 F3 I O4'
_chemical_formula_weight         490.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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
;
2019-12-23 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.504(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2645(2)
_cell_length_b                   22.2327(6)
_cell_length_c                   18.2492(5)
_cell_measurement_reflns_used    14088
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      30.2730
_cell_measurement_theta_min      2.1370
_cell_volume                     3683.36(17)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.881
_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  84.00   0.50    3.06    --   10.14  57.00 -90.00  162
  2  \w    -12.00  81.00   0.50    3.06    --   10.14  57.00  90.00  186
  3  \w    -26.00  -1.00   0.50    3.06    --   -9.05 -99.00  30.00   50
  4  \w    -24.00  28.00   0.50    3.06    --   10.14 -99.00  90.00  104
  5  \w     33.00  59.00   0.50    3.06    --   10.14-143.00  89.00   52
  6  \w    -26.00  15.00   0.50    3.06    --   -9.05 -99.00 -90.00   82
  7  \w     11.00  54.00   0.50    3.06    --   10.14-127.00-100.00   86
  8  \w    -25.00  42.00   0.50    3.06    --   10.14 -99.00 -30.00  134
  9  \w    -24.00  46.00   0.50    3.06    --   10.14 -99.00 -60.00  140
 10  \w    -13.00  48.00   0.50    3.06    --   10.14 -99.00 120.00  122
 11  \w    -73.00 -31.00   0.50    3.06    --   -9.05 -57.00-180.00   84
;
_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      0.0606674000
_diffrn_orient_matrix_UB_12      0.0148044000
_diffrn_orient_matrix_UB_13      0.0226757000
_diffrn_orient_matrix_UB_21      0.0294529000
_diffrn_orient_matrix_UB_22      -0.0282118000
_diffrn_orient_matrix_UB_23      0.0136900000
_diffrn_orient_matrix_UB_31      0.0394532000
_diffrn_orient_matrix_UB_32      -0.0017124000
_diffrn_orient_matrix_UB_33      -0.0294997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28911
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.345
_diffrn_reflns_theta_min         2.157
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54322
_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    1.768
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.060
_refine_diff_density_min         -1.779
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         8822
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0867P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.711
_reflns_number_gt                7925
_reflns_number_total             8822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10080f2.cif
_cod_data_source_block           tpt-14-10
_cod_depositor_comments
'Adding full bibliography for 7126465--7126470.cif.'
_cod_database_code               7126469
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.716
_shelx_estimated_absorpt_t_min   0.716
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.91(3)
 0.09(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C00O(H00O), C012(H012), C01A(H01A), C01C(H01H)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00N(H00N), C00X(H00X), C00Z(H00Z), C013(H013), C014(H014),
 C015(H015), C016(H016), C018(H018), C019(H019), C01G(H01L), C01H(H01M)
3.c Idealised Me refined as rotating group:
 C00J(H00A,H00B,H00C), C01B(H01E,H01F,H01G), C01E(H01I,H01J,H01K), C01F(H01B,
 H01C,H01D)
;
_shelx_res_checksum              20981
_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 2.361
_oxdiff_exptl_absorpt_empirical_full_min 0.463