Macrocyclization of carbon dioxide with 3-triflyloxybenzynes and tetrahydrofuran: straightforward access to 14-membered macrolactones.
Liu, Hongjian; Jiang, Huanfeng; Qi, Chaorong; Chemical communications (Cambridge, England) 60 (2024) 6639–6642; doi:10.1039/d4cc01229a

data_7133134
_publ_section_title
;
 Macrocyclization of carbon dioxide with 3-triflyloxybenzynes and
 tetrahydrofuran: straightforward access to 14-membered macrolactones.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6639
_journal_page_last               6642
_journal_paper_doi               10.1039/d4cc01229a
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H23 F3 O7 S'
_chemical_formula_sum            'C18 H23 F3 O7 S'
_chemical_formula_weight         440.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-03-12 deposited with the CCDC.	2024-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8302(5)
_cell_length_b                   11.4492(6)
_cell_length_c                   20.2930(10)
_cell_measurement_reflns_used    2868
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.642
_cell_measurement_theta_min      2.515
_cell_volume                     2051.60(19)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10948
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.042
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1249 before and 0.0580 after correction. The Ratio of minimum to maximum transmission is 0.8712. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0373P)^2^+0.1806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2990
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01229a2.cif
_cod_data_source_block           et_0m
_cod_depositor_comments
'Adding full bibliography for 7133133--7133135.cif.'
_cod_database_code               7133134
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.968
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C4(H4A,H4B), C2(H2A,H2B), C8(H8A,H8B), C3(H3A,
 H3B), C6(H6A,H6B), C7(H7A,H7B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'