Iron-catalyzed cascade C-C/C-O bond formation of 2,4-dienals with donor-acceptor cyclopropanes: access to functionalized hexahydrocyclopentapyrans.
Mishra, Manmath; Verma, Kshitiz; Banerjee, Sonbidya; Punniyamurthy, Tharmalingam; Chemical communications (Cambridge, England) 60 (2024) 2788–2791; doi:10.1039/d3cc06261a

data_7132698
_publ_section_title
;
 Iron-catalyzed cascade C-C/C-O bond formation of 2,4-dienals with
 donor-acceptor cyclopropanes: access to functionalized
 hexahydrocyclopentapyrans.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2788
_journal_page_last               2791
_journal_paper_doi               10.1039/d3cc06261a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H26 O5 S'
_chemical_formula_sum            'C24 H26 O5 S'
_chemical_formula_weight         426.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-09-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-10-03 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.372(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.416(4)
_cell_length_b                   19.090(8)
_cell_length_c                   11.659(5)
_cell_measurement_reflns_used    5870
_cell_measurement_temperature    137.00
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.22
_cell_volume                     2128.1(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      137.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52329
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.105
_diffrn_reflns_theta_min         2.134
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6950
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1142 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9323.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.131
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0633
_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^)+(0.1161P)^2^+2.5829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.1949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4194
_reflns_number_total             4663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06261a2.cif
_cod_data_source_block           mm_0m_a
_cod_depositor_comments          'Adding full bibliography for 7132698.cif.'
_cod_original_cell_volume        2128.2(15)
_cod_database_code               7132698
_shelx_shelxl_version_number     2019/1
_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 Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              88832
_shelx_hkl_checksum              15721
_olex2_submission_special_instructions 'No special instructions were received'