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_7132197
_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         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2gw3gy
_audit_creation_date             2023-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-22 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                113.894(3)
_cell_angle_beta                 94.988(3)
_cell_angle_gamma                92.070(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4793(2)
_cell_length_b                   11.0980(4)
_cell_length_c                   12.6043(4)
_cell_measurement_reflns_used    5545
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.5090
_cell_measurement_theta_min      3.8390
_cell_volume                     695.97(5)
_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      100.01(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 0.983
_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   -105.00 -17.00   1.00    1.00    --  -35.82 -38.00  90.00   88
  2  \w   -105.00 -17.00   1.00    1.00    --  -35.82 -38.00  60.00   88
  3  \w   -105.00 -17.00   1.00    1.00    --  -35.82 -38.00 -30.00   88
  4  \w   -108.00 -37.00   1.00    1.00    --  -35.82 178.00-150.00   71
  5  \w    -21.00  63.00   1.00    1.00    --   35.82 -77.00-150.00   84
  6  \w      6.00  74.00   1.00    1.00    --   35.82 -99.00  90.00   68
  7  \w     61.00 108.00   1.00    1.00    --   35.82 178.00   0.00   47
  8  \w      6.00  74.00   1.00    1.00    --   35.82 -99.00  60.00   68
  9  \w      6.00  74.00   1.00    1.00    --   35.82 -99.00-180.00   68
 10  \w      6.00  74.00   1.00    1.00    --   35.82 -99.00 -60.00   68
 11  \w    103.00 176.00   1.00    1.00    --  108.40  77.00 -30.00   73
 12  \w     37.00 147.00   1.00    1.00    --  108.40 -15.00-120.00  110
 13  \w     42.00 126.00   1.00    1.00    --  108.40 -61.00 -90.00   84
 14  \w     41.00 109.00   1.00    1.00    --  108.40-111.00 -30.00   68
 15  \w    103.00 176.00   1.00    1.00    --  108.40  77.00 -90.00   73
 16  \w     41.00 135.00   1.00    1.00    --  108.40 -77.00  30.00   94
 17  \w     38.00 130.00   1.00    1.00    --  108.40 -30.00 -60.00   92
 18  \w     39.00 107.00   1.00    1.00    --  108.40 -94.00-120.00   68
 19  \w     39.00 107.00   1.00    1.00    --  108.40 -94.00 -30.00   68
 20  \w     38.00 130.00   1.00    1.00    --  108.40 -30.00  30.00   92
 21  \w     41.00 109.00   1.00    1.00    --  108.40-111.00 120.00   68
 22  \w     40.00 126.00   1.00    1.00    --  108.40 -45.00-180.00   86
 23  \w     91.00 177.00   1.00    1.00    --  108.40  45.00 -30.00   86
 24  \w     91.00 177.00   1.00    1.00    --  108.40  45.00-120.00   86
 25  \w     41.00 109.00   1.00    1.00    --  108.40-111.00-150.00   68
 26  \w   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00-150.00   84
 27  \w    -65.00  36.00   1.00    1.00    --  -35.82  19.00  90.00  101
 28  \w   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00 -90.00   84
 29  \w   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00 150.00   84
 30  \w   -103.00 -19.00   1.00    1.00    --  -35.82 -57.00 -30.00   84
 31  \w     19.00  93.00   1.00    1.00    --   35.82  57.00  90.00   74
 32  \w    -31.00  -3.00   1.00    1.00    --   35.82 -57.00 120.00   28
;
_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      -0.0369684000
_diffrn_orient_matrix_UB_12      0.1441723000
_diffrn_orient_matrix_UB_13      0.0196735000
_diffrn_orient_matrix_UB_21      -0.2793080000
_diffrn_orient_matrix_UB_22      -0.0346148000
_diffrn_orient_matrix_UB_23      -0.0305862000
_diffrn_orient_matrix_UB_31      -0.0276628000
_diffrn_orient_matrix_UB_32      0.0347807000
_diffrn_orient_matrix_UB_33      0.1295067000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.757
_diffrn_reflns_theta_min         3.860
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.630
_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    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0472P)^2^+0.2816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2501
_reflns_number_total             2683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04234k2.cif
_cod_data_source_block           kwj-2022-346
_cod_original_cell_volume        695.97(4)
_cod_database_code               7132197
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.834
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              13943
_shelx_hkl_checksum              85525
_olex2_date_sample_data_collection 2023-02-15
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.821