Lewis acid-promoted cascade reactions of cyclopropenes: a unified approach to stereoselective synthesis of cyclic ethers and oxaspirolactones
Gharpure, Santosh J.; Gupta, Krishna S.; Yadav, Rakhi; Chemical Communications 61 (2025) 9705–9708; doi:10.1039/D5CC00925A

data_7134627
_publ_section_title
;
 Lewis acid-promoted cascade reactions of cyclopropenes: a unified
 approach to stereoselective synthesis of cyclic ethers and
 oxaspirolactones
;
_journal_issue                   53
_journal_name_full               'Chemical Communications'
_journal_page_first              9705
_journal_page_last               9708
_journal_paper_doi               10.1039/D5CC00925A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '4(C14 H16 O3)'
_chemical_formula_sum            'C56 H64 O12'
_chemical_formula_weight         929.07
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-09-15 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.356(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0684(3)
_cell_length_b                   17.5734(5)
_cell_length_c                   26.7319(9)
_cell_measurement_reflns_used    4132
_cell_measurement_temperature    105.00(10)
_cell_measurement_theta_max      24.8080
_cell_measurement_theta_min      2.4310
_cell_volume                     4700.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      105.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f     54.27 238.27   1.00    2.00   9.42 -12.98 -31.50    --   184
  2  \f   -111.92  72.08   1.00    2.00  16.12 -12.98 -59.25    --   184
  3  \f    -58.56 126.44   1.00    2.00  77.88 -12.98  31.50    --   185
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0612122000
_diffrn_orient_matrix_UB_12      0.0190579000
_diffrn_orient_matrix_UB_13      -0.0021335000
_diffrn_orient_matrix_UB_21      0.0309741000
_diffrn_orient_matrix_UB_22      -0.0212474000
_diffrn_orient_matrix_UB_23      0.0206416000
_diffrn_orient_matrix_UB_31      0.0178442000
_diffrn_orient_matrix_UB_32      -0.0285357000
_diffrn_orient_matrix_UB_33      -0.0167972000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1180
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            65522
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.922
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053
_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     613
_refine_ls_number_reflns         8251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0611P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4721
_reflns_number_total             8251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00925a2.cif
_cod_data_source_block           sjg_ksg_11_1430_a_1h_autored
_cod_depositor_comments          'Adding full bibliography for 7134627.cif.'
_cod_database_code               7134627
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.940
_reflns_odcompleteness_completeness 86.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.25
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00Q), C00H(H00H), C00I(H00I), C00Y(H00Y)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00M,H00N), C00O(H00R,H00S), C00Q(H00O,H00P), C00T(H00C,H00D), C00U(H00E,
 H00F), C00V(H00G,H00J), C00W(H00A,H00B), C00X(H00K,H00L), C00Z(H00T,H00U),
 C012(H01A,H01B), C013(H1,H), C016(H01I,H01J), C01A(H01P,H01Q), C01B(H2,HA),
 C01C(H3,HB), C01E(H01C,H01D), C01F(H01S,H01T), C01H(H01U,H01V), C01J(H01E,
 H01F), C01S(H01G,H01H)
2.c Aromatic/amide H refined with riding coordinates:
 C011(H011), C014(H014), C015(H015), C018(H018), C019(H019), C01D(H4),
 C01G(H01K), C01I(H01N), C01K(H5), C01L(H01L), C01M(H01M), C01N(H01O), C01O(H6),
  C01P(H01W), C01Q(H01X), C01R(H01R), C01T(H7), C01U(H01Y), C01V(H01Z),
 C01W(H01)
;
_shelx_res_checksum              6490
_shelx_hkl_checksum              21427
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.757