AgOTf-catalyzed cascade annulation of 5-hexyn-1-ols and aldehydes: enabling the diastereoselective synthesis of [6,6,6]-trioxa-fused ketals and hexahydro-2<i>H</i>-chromenes.
Vinodkumar, Ramavath; Nakate, Ashwini K.; Krishna, Gamidi Rama; Kontham, Ravindar; Chemical communications (Cambridge, England) 61 (2025) 973–976; doi:10.1039/d4cc05546b

data_7134047
_publ_section_title
;
 AgOTf-catalyzed cascade annulation of 5-hexyn-1-ols and aldehydes:
 enabling the diastereoselective synthesis of [6,6,6]-trioxa-fused ketals
 and hexahydro-2<i>H</i>-chromenes.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              973
_journal_page_last               976
_journal_paper_doi               10.1039/d4cc05546b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C19 H25 Cl O3'
_chemical_formula_sum            'C19 H25 Cl O3'
_chemical_formula_weight         336.84
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-02-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.719(3)
_cell_length_b                   12.729(2)
_cell_length_c                   8.8925(17)
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.79
_cell_volume                     1666.1(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.1605
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            54108
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.676
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1352 before and 0.0961 after correction.
The Ratio of minimum to maximum transmission is 0.8778.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       Plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.949
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0903
_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^)+(0.0638P)^2^+8.3943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1612
_reflns_number_total             1885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05546b2.cif
_cod_data_source_block           5as
_cod_depositor_comments
'Adding full bibliography for 7134046--7134049.cif.'
_cod_database_code               7134047
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              59737
_shelx_hkl_checksum              26835
_olex2_submission_special_instructions 'No special instructions were received'