Enolate addition to bicyclobutanes enables expedient access to 2-oxo-bicyclohexane scaffolds
Woelk, Kyla; Dhake, Kushal; Schley, Nathan D.; Leitch, David; Chemical Communications  (2023) –; doi:10.1039/D3CC04234K

data_7132199
_publ_section_title
;
 Enolate addition to bicyclobutanes enables expedient access to
 2-oxo-bicyclohexane scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04234K
_journal_year                    2023
_chemical_formula_moiety         'C18 H24 N2 O3'
_chemical_formula_sum            'C18 H24 N2 O3'
_chemical_formula_weight         316.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-29 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9398(2)
_cell_length_b                   12.0803(2)
_cell_length_c                   16.6377(3)
_cell_measurement_reflns_used    11115
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6720
_cell_measurement_theta_min      5.2750
_cell_volume                     3203.72(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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 -39.00   1.00    1.00    --  -35.84-178.00  30.00   69
  2  \w   -107.00  -6.00   1.00    1.00    --  -35.84 -19.00 -60.00  101
  3  \w   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00 150.00   88
  4  \w   -108.00 -39.00   1.00    1.00    --  -35.84-178.00 120.00   69
  5  \w     61.00 108.00   1.00    1.00    --   35.84 178.00 150.00   47
  6  \w     19.00 103.00   1.00    1.00    --   35.84  57.00  60.00   84
  7  \w      6.00  74.00   1.00    1.00    --   35.84 -99.00 -30.00   68
  8  \w     58.00 108.00   1.00    1.00    --   35.84-178.00-150.00   50
  9  \w     40.00 126.00   1.00    2.00    --  108.40 -45.00  60.00   86
 10  \w    103.00 176.00   1.00    2.00    --  108.40  77.00  90.00   73
 11  \w    103.00 176.00   1.00    2.00    --  108.40  77.00  30.00   73
 12  \w     40.00 124.00   1.00    2.00    --  108.40-140.00 -70.00   84
 13  \w    104.00 175.00   1.00    2.00    --  108.40 111.00  60.00   71
 14  \w     39.00 107.00   1.00    2.00    --  108.40 -94.00   0.00   68
 15  \w     39.00 107.00   1.00    2.00    --  108.40 -94.00 150.00   68
 16  \w     42.00 126.00   1.00    2.00    --  108.40 -61.00   0.00   84
 17  \w     39.00 107.00   1.00    2.00    --  108.40 -94.00 -90.00   68
 18  \w   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00-120.00   88
 19  \w    -55.00  -1.00   1.00    1.00    --  -35.84  38.00 -30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0276042000
_diffrn_orient_matrix_UB_12      -0.0743363000
_diffrn_orient_matrix_UB_13      0.0703169000
_diffrn_orient_matrix_UB_21      0.0370496000
_diffrn_orient_matrix_UB_22      -0.0839609000
_diffrn_orient_matrix_UB_23      -0.0601170000
_diffrn_orient_matrix_UB_31      0.0849046000
_diffrn_orient_matrix_UB_32      0.0607507000
_diffrn_orient_matrix_UB_33      0.0033883000
_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  0.0478
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.618
_diffrn_reflns_theta_min         5.308
_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  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.71a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0405P)^2^+1.3355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04234k2.cif
_cod_data_source_block           kjw-2023-423
_cod_database_code               7132199
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C18H25N2O3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              71860
_shelx_hkl_checksum              32812
_olex2_date_sample_data_collection 2023-09-27
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.900