Asymmetric Synthesis of Cyclopentanones through Dual Lewis Acid-Catalysed [3 + 2]-Cycloaddition of Donor-Acceptor Cyclopropanes with Ketenes
Mondal, Mukulesh; Panda, Manashi; Davis, Nicholas; McKee, Vickie; Kerrigan, Nessan Joseph; Chemical Communications  (2019) –; doi:10.1039/C9CC07477E

data_7124357
_publ_section_title
;
 Asymmetric Synthesis of Cyclopentanones through Dual Lewis Acid-Catalysed
 [3 + 2]-Cycloaddition of Donor-Acceptor Cyclopropanes with Ketenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07477E
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-05 deposited with the CCDC.    2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.80413(3)
_cell_length_b                   12.83725(7)
_cell_length_c                   22.67679(12)
_cell_measurement_reflns_used    30382
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5360
_cell_measurement_theta_min      5.1880
_cell_volume                     1980.734(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     32.00  96.00   1.00    0.50    --   48.91-125.00 -30.00   64
  2  \w     33.00 115.00   1.00    0.50    --   48.91  38.00 120.00   82
  3  \w    -55.00 -30.00   1.00    0.50    --  -49.16 -57.00-150.00   25
  4  \w    -65.00 -22.00   1.00    0.50    --  -49.16 -77.00-150.00   43
  5  \w    -50.00 -23.00   1.00    0.50    --  -49.16 -77.00  30.00   27
  6  \w    -78.00 -22.00   1.00    0.50    --  -49.16 -77.00 150.00   56
  7  \w    -57.00 -22.00   1.00    0.50    --  -49.16 -77.00  90.00   35
  8  \w    -48.00 -22.00   1.00    0.50    --  -49.16 -77.00 -30.00   26
  9  \w    -55.00 -28.00   1.00    0.50    --  -49.16 -57.00   0.00   27
 10  \w    -70.00  19.00   1.00    0.50    --  -49.16  57.00 120.00   89
 11  \w   -104.00 -29.00   1.00    0.50    --  -49.16 -19.00   0.00   75
 12  \w   -117.00 -85.00   1.00    0.50    --  -49.16 -77.00 150.00   32
 13  \w    -48.00 -22.00   1.00    0.50    --  -49.16 -77.00 -90.00   26
 14  \w   -110.00 -35.00   1.00    0.50    --  -49.16 -38.00 -60.00   75
 15  \w   -147.00-121.00   1.00    1.06    --  -82.50 -74.00 160.00   26
 16  \w    -87.00 -58.00   1.00    1.06    --  -82.50 -68.00  20.96   29
 17  \w    -95.00 -55.00   1.00    1.06    --  -82.50 -77.00-180.00   40
 18  \w    -82.00 -56.00   1.00    1.06    --  -82.50 -76.00  52.90   26
 19  \w    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00 120.00   27
 20  \w    -82.00 -56.00   1.00    1.06    --  -82.50 -74.00 160.00   26
 21  \w    -81.00 -55.00   1.00    1.06    --  -82.50 -78.00 150.38   26
 22  \w    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00   0.00   27
 23  \w    -81.00 -55.00   1.00    1.06    --  -82.50 -77.00-150.00   26
 24  \w    -81.00 -55.00   1.00    1.06    --  -82.50 -77.00 -30.00   26
 25  \w    -79.00 -54.00   1.00    1.06    --  -82.50 -80.00  23.59   25
 26  \w    -87.00 -56.00   1.00    1.06    --  -82.50 -75.00  68.71   31
 27  \w    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00 -90.00   27
 28  \w    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00  90.00   27
 29  \w    -82.00 -55.00   1.00    1.06    --  -82.50 -79.00-103.47   27
 30  \w    -83.00 -57.00   1.00    1.06    --  -82.50 -76.00 134.06   26
 31  \w    -82.00 -57.00   1.00    1.06    --  -82.50 -70.00 -59.34   25
 32  \w   -112.00 -59.00   1.00    1.06    --  -82.50 -66.00-158.78   53
 33  \w    -83.00 -57.00   1.00    1.06    --  -82.50 -72.00 -75.95   26
 34  \w     74.00 155.00   1.00    1.06    --  100.40  77.00  90.00   81
 35  \w     74.00 160.00   1.00    1.06    --  100.40  77.00-150.00   86
 36  \w     76.00 159.00   1.00    1.06    --  100.40  77.00  30.00   83
 37  \w     73.00 121.00   1.00    1.06    --  100.40  77.00 -90.00   48
 38  \w     33.00  66.00   1.00    1.06    --  100.40 -61.00   0.00   33
 39  \w     37.00 108.00   1.00    1.06    --  100.40 -94.00  60.00   71
 40  \w     28.00  85.00   1.00    1.06    --  100.40 -94.00-120.00   57
 41  \w    107.00 154.00   1.00    1.06    --  100.40  77.00  60.00   47
 42  \w     75.00 102.00   1.00    1.06    --  100.40  77.00  60.00   27
 43  \w     74.00 149.00   1.00    1.06    --  100.40  77.00   0.00   75
 44  \w     75.00 153.00   1.00    1.06    --  100.40  77.00 -60.00   78
 45  \w     74.00 153.00   1.00    1.06    --  100.40  77.00-180.00   79
 46  \w     87.00 168.00   1.00    1.06    --  100.40  61.00 150.00   81
 47  \w     50.00 106.00   1.00    1.06    --  100.40 -94.00 150.00   56
 48  \w    121.00 167.00   1.00    1.06    --  100.40  62.00-106.25   46
 49  \w     36.00  66.00   1.00    1.06    --  100.40 -61.00-120.00   30
 50  \w     47.00 117.00   1.00    1.06    --  100.40-125.00 -30.00   70
 51  \w    129.00 168.00   1.00    1.06    --  100.40  77.00 120.00   39
 52  \w     38.00  64.00   1.00    1.06    --  100.40 -61.00  60.00   26
 53  \w     77.00 117.00   1.00    1.06    --  100.40  62.00-106.25   40
 54  \w     74.00 100.00   1.00    1.06    --  100.40  77.00 120.00   26
 55  \w     40.00  67.00   1.00    1.06    --  100.40 -61.00  90.00   27
 56  \w    126.00 160.00   1.00    1.06    --  100.40  77.00 -90.00   34
 57  \w     34.00 110.00   1.00    1.06    --  100.40 -94.00 -30.00   76
 58  \w     42.00  68.00   1.00    1.06    --  100.40 -61.00 150.00   26
 59  \w     76.00 151.00   1.00    1.06    --  100.40  77.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1824709000
_diffrn_orient_matrix_UB_12      0.0002966000
_diffrn_orient_matrix_UB_13      -0.0402215000
_diffrn_orient_matrix_UB_21      -0.0016613000
_diffrn_orient_matrix_UB_22      -0.1200057000
_diffrn_orient_matrix_UB_23      -0.0009728000
_diffrn_orient_matrix_UB_31      -0.1340005000
_diffrn_orient_matrix_UB_32      0.0018809000
_diffrn_orient_matrix_UB_33      -0.0547388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            43150
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.576
_diffrn_reflns_theta_min         3.899
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
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 yellow'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0381P)^2^+0.3410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3953
_reflns_number_total             4041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07477e3.cif
_cod_data_source_block           MM-XIV-9(exp_390)
_cod_original_cell_volume        1980.736(18)
_cod_database_code               7124357
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H23 O5'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              19454
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.106
_oxdiff_exptl_absorpt_empirical_full_min 0.925