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_7133135
_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         'C24 H27 F3 O7 S'
_chemical_formula_sum            'C24 H27 F3 O7 S'
_chemical_formula_weight         516.51
_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             2021-01-01
_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                65.885(2)
_cell_angle_beta                 84.653(2)
_cell_angle_gamma                77.547(2)
_cell_formula_units_Z            4
_cell_length_a                   13.4729(8)
_cell_length_b                   13.6729(8)
_cell_length_c                   14.8740(8)
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    171
_cell_measurement_theta_max      24.794
_cell_measurement_theta_min      2.485
_cell_volume                     2442.0(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      171.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_av_unetI/netI     0.1163
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28161
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_min         2.039
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1387 before and 0.0673 after correction. The Ratio of minimum to maximum transmission is 0.8410. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     707
_refine_ls_number_reflns         9942
_refine_ls_number_restraints     886
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.8987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5085
_reflns_number_total             9942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01229a2.cif
_cod_data_source_block           lhj_0m
_cod_depositor_comments
'Adding full bibliography for 7133133--7133135.cif.'
_cod_database_code               7133135
_shelx_shelxl_version_number     2018/3
_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 C(H,H,H) groups
2. Restrained distances
 C24-C25 \\sim C25-C23
 with sigma of 0.02
 C24-C21 \\sim C22-C23
 with sigma of 0.02
 O6-C22 \\sim O6-C21
 with sigma of 0.02
3. Rigid bond restraints
 S2, C03P
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C03P \\sim S2: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O14) \\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(O15)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C24) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C03P) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(S2) \\sim Ueq: with sigma of 0 and sigma for terminal atoms of 0
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: C22(0.6) H22A(0.6) H22B(0.6) C23(0.6) H23A(0.6) H23B(0.6)
 H25A(0.6) H25B(0.6) H25C(0.4) H25D(0.4) F4(0.5) F6(0.5) F5(0.5) O15(0.5)
 O13(0.5) O16(0.5) O14(0.5) C03P(0.5) C24(0.4) H24A(0.4) H24B(0.4) C21(0.4)
 H21A(0.4) H21B(0.4) F1AA(0.5) F0AA(0.5) C0AA(0.5) F15(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C23(H23A,H23B), C25(H25A,H25B), C25(H25C,H25D), C26(H26A,H26B),
 C01E(H01A,H01B), C029(H02D,H02E), C02D(H02G,H02H), C02L(H02I,H02J), C02M(H02K,
 H02L), C037(H03A,H03B), C03B(H03C,H03D), C03H(H03E,H03G), C24(H24A,H24B),
 C21(H21A,H21B)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C5(H5), C14(H14), C10(H10), C00V(H00V), C011(H011),
 C01O(H01O), C02B(H02F), C03F(H03F)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C026(H02A,H02B,H02C), C02T(H02M,H02N,H02O)
;
_olex2_submission_special_instructions 'No special instructions were received'