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_1571892
_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         'C21 H22 O2'
_chemical_formula_sum            'C21 H22 O2'
_chemical_formula_weight         306.38
_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             2024-05-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-21 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9318(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7615(2)
_cell_length_b                   6.40467(8)
_cell_length_c                   13.86477(15)
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.3010
_cell_measurement_theta_min      5.0060
_cell_volume                     1568.76(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.123a 64-bit (release 20-05-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -58.00  31.00   1.00    2.00    --  -40.91  56.00-122.00   89
  2  \w   -112.00 -19.00   1.00    2.00    --  -40.91 -56.00  95.00   93
  3  \w     91.00 171.00   1.00    8.00    --  112.00  56.00-122.00   80
  4  \w     56.00 127.00   1.00    8.00    --  112.00 -56.00  95.00   71
  5  \w     13.00  75.00   1.00    2.00    --   40.91 -99.00 -60.00   62
  6  \w     55.00  94.00   1.00    2.00    --   40.91-125.00  60.00   39
  7  \w     85.00 110.00   1.00    8.00    --  112.00  30.00-150.00   25
  8  \w    105.00 131.00   1.00    8.00    --  112.00  77.00 120.00   26
  9  \w    145.00 175.00   1.00    8.00    --  112.00  77.00 120.00   30
 10  \w    105.00 168.00   1.00    8.00    --  112.00 111.00-120.00   63
 11  \w    105.00 177.00   1.00    8.00    --  112.00  61.00 150.00   72
 12  \w    153.00 178.00   1.00    8.00    --  112.00  30.00-150.00   25
 13  \w     45.00  92.00   1.00    8.00    --  112.00-111.00  60.00   47
 14  \w     39.00 105.00   1.00    8.00    --  112.00-111.00  90.00   66
 15  \w     97.00 149.00   1.00    8.00    --  112.00  45.00-150.00   52
 16  \w    133.00 166.00   1.00    8.00    --  112.00 111.00-150.00   33
 17  \w    108.00 143.00   1.00    8.00    --  112.00 111.00 150.00   35
;
_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      -0.0644620000
_diffrn_orient_matrix_UB_12      -0.1574801000
_diffrn_orient_matrix_UB_13      0.0089572000
_diffrn_orient_matrix_UB_21      -0.0293318000
_diffrn_orient_matrix_UB_22      0.0377697000
_diffrn_orient_matrix_UB_23      -0.1070749000
_diffrn_orient_matrix_UB_31      0.0508459000
_diffrn_orient_matrix_UB_32      -0.1779010000
_diffrn_orient_matrix_UB_33      -0.0305985000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7738
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.026
_diffrn_reflns_theta_min         5.007
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.123a (Rigaku Oxford Diffraction, 2024)
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    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.673
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0008(3)
_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   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0442
_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^)+(0.0660P)^2^+0.2959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2925
_reflns_number_total             3208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02767a2.cif
_cod_data_source_block           ste-24-1162
_cod_depositor_comments
'Adding full bibliography for 1571891--1571893.cif.'
_cod_database_code               1571892
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C21 H22 O2'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.673
_olex2_refinement_description
;
;
_shelx_res_checksum              71283
_olex2_date_sample_data_collection 2024-05-21
_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 6.825
_oxdiff_exptl_absorpt_empirical_full_min 0.492