Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes.
Nicolai, Stefano; Waser, Jérôme; Chemical science 15 (2024) 10823–10829; doi:10.1039/d4sc02767a

data_1571891
_publ_section_title
;
 Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol
 ethers for the synthesis of bicyclo[4.1.1]octanes.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              10823
_journal_page_last               10829
_journal_paper_doi               10.1039/d4sc02767a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C14 H22 O2'
_chemical_formula_sum            'C14 H22 O2'
_chemical_formula_weight         222.31
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-05 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6839(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.17394(11)
_cell_length_b                   8.78352(19)
_cell_length_c                   24.0129(5)
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.7020
_cell_measurement_theta_min      5.3370
_cell_volume                     1301.63(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -17.00   9.00   1.00    4.00    --  -40.91 105.00 -83.00   26
  2  \w     33.00  65.00   1.00    4.00    --   40.91-105.00 176.00   32
  3  \w     71.00  96.00   1.00   16.00    --  112.00-105.00 176.00   25
  4  \w    106.00 161.00   1.00   16.00    --  112.00 105.00 -83.00   55
  5  \w   -111.00 -86.00   1.00    4.00    --  -40.91 -38.00  90.00   25
  6  \w    -66.00 -17.00   1.00    4.00    --  -40.91 -38.00  90.00   49
  7  \w     18.00  98.00   1.00    4.00    --   40.91  38.00 120.00   80
  8  \w     32.00  95.00   1.00    4.00    --   40.91-125.00  30.00   63
  9  \w    112.00 158.00   1.00   16.00    --  112.00  77.00-150.00   46
 10  \w    109.00 177.00   1.00   16.00    --  112.00  77.00-120.00   68
 11  \w     40.00 136.00   1.00   16.00    --  112.00 -45.00-180.00   96
 12  \w    129.00 175.00   1.00   16.00    --  112.00 111.00 -60.00   46
 13  \w     36.00  88.00   1.00   16.00    --  112.00 -94.00-150.00   52
 14  \w     65.00  91.00   1.00   16.00    --  112.00-111.00 -30.00   26
 15  \w    140.00 175.00   1.00   16.00    --  112.00  45.00   0.00   35
 16  \w    106.00 149.00   1.00   16.00    --  112.00  77.00 -90.00   43
 17  \w     72.00 106.00   1.00   16.00    --  112.00 -94.00-120.00   34
 18  \w     48.00  73.00   1.00   16.00    --  112.00-111.00  60.00   25
 19  \w     88.00 117.00   1.00   16.00    --  112.00  45.00   0.00   29
;
_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      0.0878953000
_diffrn_orient_matrix_UB_12      -0.1168606000
_diffrn_orient_matrix_UB_13      -0.0415494000
_diffrn_orient_matrix_UB_21      0.0019760000
_diffrn_orient_matrix_UB_22      -0.1228121000
_diffrn_orient_matrix_UB_23      0.0458000000
_diffrn_orient_matrix_UB_31      -0.2335549000
_diffrn_orient_matrix_UB_32      -0.0450114000
_diffrn_orient_matrix_UB_33      -0.0172554000
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.945
_diffrn_reflns_theta_min         3.683
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.616
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0525P)^2^+0.2480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2387
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02767a2.cif
_cod_data_source_block           ste-23-991
_cod_depositor_comments
'Adding full bibliography for 1571891--1571893.cif.'
_cod_original_cell_volume        1301.63(4)
_cod_database_code               1571891
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C14 H22 O2'
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.717
_olex2_refinement_description
;
;
_shelx_res_checksum              12742
_olex2_date_sample_data_collection 2023-12-05
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.476
_oxdiff_exptl_absorpt_empirical_full_min 0.480