Macrocyclization of 3-triflyloxybenzynes with tetrahydrofuran via an anionic thia-Fries rearrangement.
Cheng, Ruixiang; Xiong, Wenfang; Qi, Chaorong; Wang, Lu; Ren, Yanwei; Jiang, Huanfeng; Chemical communications (Cambridge, England) 56 (2020) 6495–6498; doi:10.1039/d0cc00135j

data_7126494
_publ_section_title
;
 Macrocyclization of 3-triflyloxybenzynes with tetrahydrofuran via an
 anionic thia-Fries rearrangement.
;
_journal_issue                   48
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6495
_journal_page_last               6498
_journal_paper_doi               10.1039/d0cc00135j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C19 H23.27 F3 O6 S'
_chemical_formula_sum            'C19 H24.04 F3 O6 S'
_chemical_formula_weight         437.48
_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     direct
_audit_creation_date             2018-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-12-23 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                94.471(5)
_cell_angle_beta                 104.322(6)
_cell_angle_gamma                108.484(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3575(6)
_cell_length_b                   10.2713(6)
_cell_length_c                   11.5278(7)
_cell_measurement_reflns_used    4707
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.1110
_cell_measurement_theta_min      2.5890
_cell_volume                     1003.31(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -88.00  21.00   1.00    5.00    --  -11.59 -77.00-150.00  109
  2  \w    -60.00  40.00   1.00    5.00    --   11.74 -57.00 -30.00  100
  3  \w    -16.00  85.00   1.00    5.00    --   11.74  57.00 120.00  101
  4  \w     34.00  99.00   1.00    5.00    --   11.74-178.00 -30.00   65
  5  \w    -13.00  28.00   1.00    5.00    --   11.74  37.00  30.00   41
  6  \w    -20.00  53.00   1.00    5.00    --   11.74 -99.00 150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0765336000
_diffrn_orient_matrix_UB_12      -0.0187115000
_diffrn_orient_matrix_UB_13      0.0074777000
_diffrn_orient_matrix_UB_21      0.0256426000
_diffrn_orient_matrix_UB_22      -0.0268836000
_diffrn_orient_matrix_UB_23      0.0530161000
_diffrn_orient_matrix_UB_31      0.0212010000
_diffrn_orient_matrix_UB_32      0.0662341000
_diffrn_orient_matrix_UB_33      0.0358648000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.122
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.589
_refine_diff_density_min         -1.564
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1776P)^2^+7.5871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3224
_refine_ls_wR_factor_ref         0.3380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2932
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00135j2.cif
_cod_data_source_block           crx-440
_cod_depositor_comments          'Adding full bibliography for 7126494.cif.'
_cod_database_code               7126494
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.98
_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
2. Rigid bond restraints
 C14, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim O5: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
S1 \\sim C19: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
O5 \\sim C15: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C19) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(H12A)=Sof(H12B)=Sof(H14A)=Sof(C00V)=1-FVAR(1)
 Sof(H14)=Sof(C13)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C7(H7A,H7B), C16(H16A,H16B), C15(H15A,H15B),
 C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3), C14(H14), C14(H14A), C13(H13), C00V(H00V)
;
_olex2_date_sample_data_collection 2018-02-26
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.608