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_1571893
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-20 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                67.728(3)
_cell_angle_beta                 74.021(2)
_cell_angle_gamma                82.9324(19)
_cell_formula_units_Z            2
_cell_length_a                   8.11476(18)
_cell_length_b                   10.4720(2)
_cell_length_c                   10.7595(4)
_cell_measurement_reflns_used    11017
_cell_measurement_temperature    140.00(10)
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_cell_measurement_theta_min      4.5480
_cell_volume                     813.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.105a 64-bit (release 11-01-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
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_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_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   -108.00 -34.00   0.50    0.20    --  -76.25 132.00  74.01  148
  2  \w   -108.00 -34.00   0.50    0.20    --  -76.25 132.00  74.01  148
  3  \w   -108.00 -33.00   0.50    0.20    --  -70.95   0.00 -60.00  150
  4  \w   -108.00 -33.00   0.50    0.20    --  -70.95   0.00 -60.00  150
  5  \w   -112.00 -80.00   0.50    0.20    --  -76.25 -76.00 -62.27   64
  6  \w   -118.00 -86.00   0.50    0.20    --  -76.25 -60.00   7.60   64
  7  \w    -74.00 -43.00   0.50    0.20    --  -36.00 -69.00 132.42   62
  8  \w   -115.00 -84.00   0.50    0.20    --  -76.25 -67.00 149.39   62
  9  \w   -119.00 -86.00   0.50    0.20    --  -76.25 -56.00 139.53   66
 10  \w   -112.00 -79.00   0.50    0.20    --  -68.00 -52.00 104.70   66
 11  \w   -118.00 -85.00   0.50    0.20    --  -72.00 -41.00  65.33   66
 12  \w   -123.00 -86.00   0.50    0.20    --  -76.25 -36.00  71.26   74
 13  \w   -114.00 -81.00   0.50    0.20    --  -68.00 -41.00  27.86   66
 14  \w    -74.00 -43.00   0.50    0.20    --  -36.00 -69.00-154.64   62
 15  \w   -121.00 -87.00   0.50    0.20    --  -76.25 -50.00-175.47   68
 16  \w   -112.00 -79.00   0.50    0.20    --  -76.25 -90.00 -16.61   66
 17  \w     46.00  77.00   0.50    0.20    --   40.00  72.00-136.17   62
 18  \w     40.00  72.00   0.50    0.20    --   36.00  76.00  54.40   64
 19  \w     45.00  77.00   0.50    0.20    --   40.00  74.00 113.73   64
 20  \w     51.00  84.00   0.50    0.20    --   40.00  53.00  29.85   66
 21  \w     47.00  74.00   0.50    0.20    --   79.75   2.00 -37.28   54
 22  \w     62.00  94.00   0.50    0.20    --   52.00  58.00 -51.26   64
 23  \w     69.00 101.00   0.50    0.20    --   60.00  62.00-132.95   64
 24  \w     62.00  95.00   0.50    0.20    --   52.00  57.00 -93.10   66
 25  \w     91.00 116.00   0.50    0.20    --   79.75  49.00 -36.70   50
 26  \w     94.00 125.00   0.50    0.20    --   79.75  35.00 -51.64   62
 27  \w     77.00 105.00   0.50    0.20    --   79.75  26.00 -78.77   56
 28  \w     73.00 106.00   0.50    0.20    --   79.75  25.00 -44.42   66
 29  \w    100.00 126.00   0.50    0.20    --   79.75  32.00  -7.85   52
 30  \w     45.00 110.00   0.50    0.20    --   79.75   3.00-131.14  130
 31  \w     79.00 110.00   0.50    0.20    --   79.75   3.00-101.06   62
 32  \w     97.00 124.00   0.50    0.20    --   79.75  46.00  25.36   54
 33  \w     94.00 121.00   0.50    0.20    --   79.75   6.00 152.15   54
 34  \w     58.00  88.00   0.50    0.20    --   79.75   6.00 152.15   60
 35  \w     35.00 103.00   0.50    0.20    --   76.40-125.00  90.00  136
 36  \w     35.00 103.00   0.50    0.20    --   76.40-125.00 150.00  136
 37  \w     35.00 103.00   0.50    0.20    --   76.40-125.00 120.00  136
 38  \w     35.00 103.00   0.50    0.20    --   76.40-125.00  90.00  136
 39  \w     35.00 103.00   0.50    0.20    --   76.40-125.00 -30.00  136
 40  \w     35.00 103.00   0.50    0.20    --   76.40-125.00 -90.00  136
 41  \w     49.00 103.00   0.50    0.20    --   76.40-125.00-150.00  108
 42  \w     40.00 105.00   0.50    0.20    --   79.75-123.00-137.96  130
 43  \w     38.00  84.00   0.50    0.20    --   75.71 -95.00-150.00   92
 44  \w     48.00  99.00   0.50    0.20    --   79.75-113.00 -76.36  102
 45  \w     39.00  85.00   0.50    0.20    --   76.40 -95.00 -30.00   92
 46  \w     39.00  85.00   0.50    0.20    --   76.40 -95.00-120.00   92
 47  \w     41.00 105.00   0.50    0.20    --   79.75-122.00  36.50  128
 48  \w     46.00  91.00   0.50    0.20    --   79.75-100.00  71.83   90
 49  \w     39.00  85.00   0.50    0.20    --   76.40 -95.00  90.00   92
 50  \w     39.00  85.00   0.50    0.20    --   76.40 -95.00 150.00   92
 51  \w     39.00  85.00   0.50    0.20    --   76.40 -95.00 120.00   92
 52  \w     38.00  84.00   0.50    0.20    --   75.71 -95.00  30.00   92
 53  \w     39.00  85.00   0.50    0.20    --   76.40 -95.00   0.00   92
 54  \w     26.00  72.00   0.50    0.20    --   63.71 -95.00 -30.00   92
 55  \w     38.00  84.00   0.50    0.20    --   75.71 -95.00 -60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170050000
_diffrn_orient_matrix_UB_12      -0.0087649000
_diffrn_orient_matrix_UB_13      0.1421478000
_diffrn_orient_matrix_UB_21      0.0900846000
_diffrn_orient_matrix_UB_22      0.1399457000
_diffrn_orient_matrix_UB_23      -0.0691481000
_diffrn_orient_matrix_UB_31      -0.1749574000
_diffrn_orient_matrix_UB_32      0.0749796000
_diffrn_orient_matrix_UB_33      0.0231179000
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17602
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.563
_diffrn_reflns_theta_min         4.564
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (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    1.251
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0025(8)
_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     297
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0571P)^2^+0.2306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2901
_reflns_number_total             3274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02767a2.cif
_cod_data_source_block           ste-24-1037
_cod_depositor_comments
'Adding full bibliography for 1571891--1571893.cif.'
_cod_database_code               1571893
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C21 H22 O2'
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.880
_olex2_refinement_description
;
;
_shelx_res_checksum              88477
_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 1.814
_oxdiff_exptl_absorpt_empirical_full_min 0.519