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_7133133
_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_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_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             2020-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-15 deposited with the CCDC.	2024-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                88.037(2)
_cell_angle_beta                 83.186(3)
_cell_angle_gamma                89.353(3)
_cell_formula_units_Z            4
_cell_length_a                   10.7822(9)
_cell_length_b                   10.9047(9)
_cell_length_c                   12.0558(10)
_cell_measurement_reflns_used    1974
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.867
_cell_measurement_theta_min      2.398
_cell_volume                     1406.6(2)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_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  0.0960
_diffrn_reflns_av_unetI/netI     0.1324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16097
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.398
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0962 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.8884. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5707
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1937
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0412P)^2^+0.1113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2546
_reflns_number_total             5707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01229a2.cif
_cod_data_source_block           0914lhj1_0m
_cod_depositor_comments
'Adding full bibliography for 7133133--7133135.cif.'
_cod_database_code               7133133
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C25-C28 \\sim C26-C28 \\sim C24-C23 \\sim C27-C23 \\sim C24-C25 \\sim C26-C27
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C25) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C24)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: H23C(0.6) H23D(0.6) H23A(0.4) H23B(0.4) H28C(0.6) H28D(0.6)
 H28A(0.4) H28B(0.4) C27(0.6) H27A(0.6) H27B(0.6) C26(0.6) H26A(0.6) H26B(0.6)
 C25(0.4) H25A(0.4) H25B(0.4) C24(0.4) H24A(0.4) H24B(0.4)
5.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C3(H3A,H3B), C31(H31A,H31B), C30(H30A,H30B), C14(H14A,H14B),
 C29(H29A,H29B), C4(H4A,H4B), C13(H13A,H13B), C15(H15A,H15B), C2(H2A,H2B),
 C12(H12A,H12B), C1(H1A,H1B), C23(H23C,H23D), C23(H23A,H23B), C28(H28C,H28D),
 C28(H28A,H28B), C27(H27A,H27B), C26(H26A,H26B), C25(H25A,H25B), C24(H24A,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C9(H9), C10(H10), C8(H8), C18(H18)
5.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'