Bi(OTf)3-catalysed intramolecular cyclisation of unsaturated acetals
Saget, Raphaël; Jaunky, Piotr; Duñach, Elisabet; RSC Advances 11 (2021) 21066–21072; doi:10.1039/D1RA03686F

data_7243055
_publ_section_title
;
 Bi(OTf)3-catalysed intramolecular cyclisation of unsaturated acetals
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              21066
_journal_page_last               21072
_journal_paper_doi               10.1039/D1RA03686F
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C15 H24 O5'
_chemical_formula_sum            'C15 H24 O5'
_chemical_formula_weight         284.34
_chemical_name_common            'cyclic diester'
_chemical_name_systematic        2c
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7684(2)
_cell_length_b                   7.58720(10)
_cell_length_c                   12.5827(2)
_cell_measurement_reflns_used    15263
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.7540
_cell_measurement_theta_min      2.5720
_cell_volume                     1597.48(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00  32.00   1.00    1.00    --  -40.54  65.00 -31.00  102
  2  \w   -113.00 -11.00   1.00    1.00    --  -40.54 -65.00-167.00  102
  3  \w    -32.00  70.00   1.00    1.00    --   40.54 -65.00-167.00  102
  4  \w     76.00 178.00   1.00    5.00    --  105.59  65.00 -31.00  102
  5  \w     33.00 135.00   1.00    5.00    --  105.59 -65.00-167.00  102
  6  \w     23.00  97.00   1.00    1.00    --   40.54-125.00-150.00   74
  7  \w     11.00 113.00   1.00    1.00    --   40.54  65.00 -31.00  102
  8  \w     23.00  97.00   1.00    1.00    --   40.54-125.00 120.00   74
  9  \w     16.00 115.00   1.00    1.00    --   40.54  38.00  90.00   99
 10  \w     32.00 118.00   1.00    5.00    --  105.59-125.00-150.00   86
 11  \w     76.00 178.00   1.00    5.00    --  105.59  61.00  90.00  102
 12  \w     80.00 178.00   1.00    5.00    --  105.59  45.00 -90.00   98
 13  \w     33.00 131.00   1.00    5.00    --  105.59 -45.00 -30.00   98
 14  \w     76.00 178.00   1.00    5.00    --  105.59  61.00  60.00  102
 15  \w     76.00 178.00   1.00    5.00    --  105.59  61.00  30.00  102
 16  \w     80.00 178.00   1.00    5.00    --  105.59  45.00 -60.00   98
 17  \w     80.00 178.00   1.00    5.00    --  105.59  45.00   0.00   98
 18  \w     77.00 178.00   1.00    5.00    --  105.59  30.00 120.00  101
 19  \w     80.00 178.00   1.00    5.00    --  105.59  45.00  90.00   98
 20  \w     94.00 178.00   1.00    5.00    --  105.59 125.00-120.00   84
 21  \w   -113.00 -12.00   1.00    1.00    --  -40.54 -57.00 -30.00  101
 22  \w    -65.00  34.00   1.00    1.00    --  -40.54  38.00  90.00   99
 23  \w   -117.00  -8.00   1.00    1.00    --  -40.54 -77.00 -60.00  109
 24  \w      8.00 117.00   1.00    1.00    --   40.54  77.00 120.00  109
 25  \w      1.00  81.00   1.00    1.00    --   40.54 -99.00  30.00   80
 26  \w      8.00 117.00   1.00    1.00    --   40.54  77.00-150.00  109
 27  \w     80.00 178.00   1.00    5.00    --  105.59  45.00-180.00   98
 28  \w     76.00 178.00   1.00    5.00    --  105.59  61.00-180.00  102
 29  \w     76.00 178.00   1.00    5.00    --  105.59  61.00 -60.00  102
 30  \w     76.00 178.00   1.00    5.00    --  105.59  61.00-120.00  102
 31  \w     73.00 178.00   1.00    5.00    --  105.59  77.00 120.00  105
 32  \w     76.00 178.00   1.00    5.00    --  105.59  61.00-150.00  102
 33  \w     23.00 109.00   1.00    5.00    --  105.59 -94.00   0.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0876795000
_diffrn_orient_matrix_UB_12      0.0327538000
_diffrn_orient_matrix_UB_13      0.0392654000
_diffrn_orient_matrix_UB_21      0.0048898000
_diffrn_orient_matrix_UB_22      0.1518246000
_diffrn_orient_matrix_UB_23      -0.0806226000
_diffrn_orient_matrix_UB_31      -0.0276337000
_diffrn_orient_matrix_UB_32      0.1308561000
_diffrn_orient_matrix_UB_33      0.0837087000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29075
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.838
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: cyclohexane'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0557
_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^)+(0.0837P)^2^+0.3904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             3175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra03686f2.cif
_cod_data_source_block           ref2c
_cod_database_code               7243055
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.823
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.c X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              58067
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.755