Three-component heteroannulation for tetrasubstituted furan construction enabled by successive defluorination and dual sulfonylation relay
Cai, Song-Zhou; Ge, Danhua; Sun, Li-Wen; Rao, Weidong; Wang, Xin; Shen, Zhi-Liang; Chu, Xue-Qiang; Green Chemistry 23 (2021) 935–941; doi:10.1039/D0GC03922E

data_7241886
_publ_section_title
;
 Three-component heteroannulation for tetrasubstituted furan construction
 enabled by successive defluorination and dual sulfonylation relay
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              935
_journal_page_last               941
_journal_paper_doi               10.1039/D0GC03922E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C20 H11 F5 O5 S4'
_chemical_formula_sum            'C20 H11 F5 O5 S4'
_chemical_formula_weight         554.53
_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             2020-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-26 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                72.297(3)
_cell_angle_beta                 85.352(3)
_cell_angle_gamma                85.778(3)
_cell_formula_units_Z            6
_cell_length_a                   7.7476(7)
_cell_length_b                   18.5104(19)
_cell_length_c                   23.642(2)
_cell_measurement_reflns_used    5894
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.51
_cell_measurement_theta_min      2.31
_cell_volume                     3215.1(5)
_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      296.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1083
_diffrn_reflns_av_unetI/netI     0.1558
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            40398
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.438
_diffrn_reflns_theta_min         2.425
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1564 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.8531. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.087
_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     1104
_refine_ls_number_reflns         13988
_refine_ls_number_restraints     713
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+1.6555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7325
_reflns_number_total             13988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03922e2.cif
_cod_data_source_block           b190729a_0m_a
_cod_depositor_comments          'Adding full bibliography for 7241886.cif.'
_cod_original_cell_volume        3215.0(5)
_cod_database_code               7241886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C37-S8 = S8-C0AA = S8-C0AA = S8-C37 = C37-S8A = S8A-C0AB = S8A-C37 = S8A-C0AB
 = S1A-C14A = S1A-C11
 1.76 with sigma of 0.02
 C37-C38A = C0AB-C39A = C33-C34 = C36-C35 = C11-C12 = C14-C13 = C17-C20 = C15-
 C16
 1.34 with sigma of 0.02
 C33-S10 = S10-C36 = C11-S1 = S1-C14 = C17-S3 = S3-C15 = C50-S14 = S14-C53 =
 S10-C36 = S10-C33 = S1-C11 = S1-C14 = S3-C17 = S3-C15 = S14-C50 = S14-C53
 1.76 with sigma of 0.02
 C33-S10A = S10A-C36A = C50-S14A = S14A-C53A = C17-S3A = S3A-C15A = C14A-S1A =
 S1A-C11
 1.76 with sigma of 0.02
 C17-C20A = C15A-C16A = C33-C34A = C36A-C35A = C50-C51 = C53-C52 = C50-C51A =
 C53A-C52A
 1.34 with sigma of 0.02
 C33-C36 = C11-C14 = C17-C15 = C50-C53 = S10-C35 = C33-C36A = C50-C53A = C17-
 C15A = C14A-C11 = C37-C0AA = C37-C0AB
 3.048 with sigma of 0.04
 S10-C34 = S1-C12 = S1-C13 = S3-C20 = S3-C16 = S14-C51 = S14-C52 = S1A-C13A =
 S1A-C12A = S8-C39 = S8-C38 = S8A-C38A = S8A-C39A
 2.693 with sigma of 0.04
 C33-C35 = C36-C34 = C11-C13 = C14-C12 = C17-C16 = C15-C20 = C17-C16A = C15A-
 C20A = C33-C35A = C36A-C34A = C50-C52 = C53-C51 = C50-C52A = C53A-C51A = C11-
 C13A = C14A-C12A = C37-C39 = C0AA-C38 = C37-C39A = C0AB-C38A
 2.434 with sigma of 0.04
3. Restrained planarity
 C37, S8A, C0AB, C39A, C38A
 with sigma of 0.1
 S8, C37, C0AA, C39, C38, S6
 with sigma of 0.1
 S10, C33, C34, C35, C36, S9
 with sigma of 0.1
 S14, S16, C50, C51, C52, C53
 with sigma of 0.1
 S4, C17, C20, C16, C15, S3
 with sigma of 0.1
 S2, C11, C12, C13, C14, S1
 with sigma of 0.1
 C33, S10A, C36A, C35A, C34A, S9
 with sigma of 0.1
 S2, C11, S1A, C14A, C13A, C12A
 with sigma of 0.1
 S4, C17, S3A, C15A, C16A, C20A
 with sigma of 0.1
 S16, C50, C51A, C52A, C53A, S14A
 with sigma of 0.1
 S2, C11, C12A, C13A, C14A, S1A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
S8 \\sim C0AA \\sim C39 \\sim C0AB \\sim C39A \\sim C38A \\sim C38 \\sim S8A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C51 \\sim C52 \\sim C53 \\sim S14A \\sim C53A \\sim C52A \\sim S14 \\sim C51A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
S1 \\sim C13 \\sim C14 \\sim C14A \\sim C13A \\sim C12A \\sim C12 \\sim S1A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C36) \\sim Ueq,
Uanis(S10) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(S3) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.002 and
sigma for terminal atoms of 0.004
5. Rigid body (RIGU) restrains
 S1, S3, C20, S10, C12, C13, C14, S14, C15, C16, C34, C35, C36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S8, C37, C0AA, C39, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C37, S8A, C0AB, C39A, C38A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C33, C34A, C35A, C36A, S10A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C11, S1A, C14A, C13A, C12A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C17, S3A, C15A, C16A, C20A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C50, C51A, C52A, C53A, S14A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S14, C51, C52, C53, S14A, C53A, C52A, C51A, S10, C34, C35, C36, C34A, C35A,
 C36A, S10A, S3, C15, C16, C20A, C16A, C15A, C20, S3A, S1, C12, C13, C14, S1A,
 C14A, C13A, C12A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C50, S14A, C53A, C52A, C51A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S14, C50, C51, C52, C53
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(S8A)=Sof(C0AB)=Sof(H0AB)=Sof(C39A)=Sof(H39A)=Sof(C38A)=Sof(H38A)=1-FVAR(1)
 Sof(S8)=Sof(C0AA)=Sof(H0AA)=Sof(C39)=Sof(H39)=Sof(C38)=Sof(H38)=FVAR(1)
 Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(H36A)=Sof(S10A)=1-FVAR(2)
 Sof(S10)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=FVAR(2)
 Sof(C20A)=Sof(H20A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(S3A)=1-FVAR(3)
 Sof(S3)=Sof(C20)=Sof(H20)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=FVAR(3)
 Sof(S1A)=Sof(C14A)=Sof(H14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=1-FVAR(4)
 Sof(S1)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=FVAR(4)
 Sof(S14A)=Sof(C53A)=Sof(H53A)=Sof(C52A)=Sof(H52A)=Sof(C51A)=Sof(H51A)=1-FVAR(5)
 Sof(S14)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=FVAR(5)
7.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C20(H20), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C34(H34), C35(H35), C36(H36), C0AA(H0AA), C39(H39), C40(H40), C41(H41),
 C42(H42), C51(H51), C52(H52), C53(H53), C55(H55), C56(H56), C57(H57), C58(H58),
  C59(H59), C38(H38), C0AB(H0AB), C39A(H39A), C38A(H38A), C34A(H34A),
 C35A(H35A), C36A(H36A), C20A(H20A), C16A(H16A), C15A(H15A), C14A(H14A),
 C13A(H13A), C12A(H12A), C53A(H53A), C52A(H52A), C51A(H51A)
;
_shelx_res_checksum              7988
_olex2_submission_special_instructions 'No special instructions were received'