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_7124358
_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                   6.80314(4)
_cell_length_b                   12.83574(7)
_cell_length_c                   22.67729(12)
_cell_measurement_reflns_used    34239
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      74.4570
_cell_measurement_theta_min      3.8850
_cell_volume                     1980.257(19)
_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      100.0(3)
_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 0.997
_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      6.00  31.00   1.00    0.50    --   38.00  90.00  26.87   25
  2  \w      9.00  34.00   1.00    0.50    --   42.00  92.00 115.26   25
  3  \w     13.00  38.00   1.00    0.50    --   46.00  92.00-127.95   25
  4  \w     34.00  65.00   1.00    0.50    --   48.91  38.00  30.00   31
  5  \w    -92.00  -9.00   1.00    0.50    --  -49.16 125.00-180.00   83
  6  \w    -60.00 -28.00   1.00    0.50    --  -49.16 -57.00 -90.00   32
  7  \w   -104.00 -29.00   1.00    0.50    --  -49.16 -19.00  90.00   75
  8  \w    -49.00 -23.00   1.00    0.50    --  -49.16 -77.00  30.00   26
  9  \w    -75.00 -31.00   1.00    0.50    --  -49.16 -48.00 -13.59   44
 10  \w   -115.00 -62.00   1.00    0.50    --  -49.16 -57.00 -90.00   53
 11  \w   -110.00 -30.00   1.00    0.50    --  -49.16 -51.00 176.93   80
 12  \w    -98.00 -55.00   1.00    0.50    --  -49.16 -77.00  30.00   43
 13  \w     19.00  44.00   1.00    0.50    --   50.00  89.00  20.20   25
 14  \w     19.00  44.00   1.00    0.50    --   50.00  90.00 129.59   25
 15  \w     18.00  43.00   1.00    0.50    --   50.00  91.00 -84.76   25
 16  \w     29.00  55.00   1.00    0.50    --   58.00  82.00 -40.71   26
 17  \w     35.00  61.00   1.00    0.50    --   62.00  78.00 -10.83   26
 18  \w     33.00  60.00   1.00    0.50    --   62.00  82.00-148.42   27
 19  \w     95.00 122.00   1.00    0.50    --   62.00  82.00-148.42   27
 20  \w     37.00  63.00   1.00    0.50    --   66.00  82.00  14.81   26
 21  \w     40.00  67.00   1.00    0.50    --   66.00  76.00-118.93   27
 22  \w    -63.00 -37.00   1.00    0.77    --  -66.00 -82.00-104.36   26
 23  \w    110.00 135.00   1.00    0.50    --   66.00  76.00-118.93   25
 24  \w     38.00  95.00   1.00    0.50    --   66.00  79.00  76.48   57
 25  \w     39.00  64.00   1.00    0.50    --   66.00  79.00 151.78   25
 26  \w     40.00  67.00   1.00    0.50    --   66.00  76.00  48.07   27
 27  \w    110.00 140.00   1.00    0.50    --   70.00  83.00 161.96   30
 28  \w     42.00  67.00   1.00    0.50    --   70.00  83.00 161.96   25
 29  \w     46.00  72.00   1.00    0.50    --   74.00  81.00-105.98   26
 30  \w    -72.00 -46.00   1.00    0.77    --  -74.00 -81.00 -99.09   26
 31  \w    -76.00 -50.00   1.00    0.77    --  -78.00 -81.00-167.38   26
 32  \w    -91.00 -22.00   1.00    0.77    --  -82.50 125.00  60.00   69
 33  \w    -81.00 -55.00   1.00    0.77    --  -82.50 -77.00   0.00   26
 34  \w    -82.00 -56.00   1.00    0.77    --  -82.50 -75.00-146.03   26
 35  \w   -105.00 -56.00   1.00    0.77    --  -82.50 -76.00  81.77   49
 36  \w    -82.00 -56.00   1.00    0.77    --  -82.50 -75.00  23.13   26
 37  \w    -81.00 -55.00   1.00    0.77    --  -82.50 -78.00-107.87   26
 38  \w    -83.00 -56.00   1.00    0.77    --  -82.50 -79.00  -9.71   27
 39  \w    -79.00 -54.00   1.00    0.77    --  -82.50 -80.00  54.40   25
 40  \w    -84.00 -57.00   1.00    0.77    --  -82.50 -72.00 127.57   27
 41  \w    -83.00 -57.00   1.00    0.77    --  -82.50 -72.00  92.79   26
 42  \w    -87.00 -55.00   1.00    0.77    --  -82.50 -78.00 116.22   32
 43  \w    -81.00 -55.00   1.00    0.77    --  -82.50 -77.00 -30.00   26
 44  \w    -82.00 -56.00   1.00    0.77    --  -82.50 -76.00 -70.97   26
 45  \w    -85.00 -58.00   1.00    0.77    --  -82.50 -69.00 -57.18   27
 46  \w    -82.00 -56.00   1.00    0.77    --  -82.50 -76.00 157.48   26
 47  \w     37.00 118.00   1.00    0.77    --  100.40-125.00  60.00   81
 48  \w     81.00 125.00   1.00    0.77    --  100.40  77.00 120.00   44
 49  \w     74.00 147.00   1.00    0.77    --  100.40  77.00 -90.00   73
 50  \w     73.00 159.00   1.00    0.77    --  100.40  77.00-180.00   86
 51  \w     98.00 164.00   1.00    0.77    --  100.40 125.00 -90.00   66
 52  \w     30.00  97.00   1.00    0.77    --  100.40 -94.00 -60.00   67
 53  \w     37.00  62.00   1.00    0.77    --  100.40 -61.00 150.00   25
 54  \w     74.00 149.00   1.00    0.77    --  100.40  77.00  60.00   75
 55  \w     75.00 156.00   1.00    0.77    --  100.40  77.00   0.00   81
 56  \w     33.00  59.00   1.00    0.77    --  100.40 -61.00 -30.00   26
 57  \w     73.00 142.00   1.00    0.77    --  100.40  77.00-150.00   69
 58  \w     38.00  91.00   1.00    0.77    --  100.40 -94.00-120.00   53
 59  \w     79.00 156.00   1.00    0.77    --  100.40  61.00 -30.00   77
 60  \w     28.00 108.00   1.00    0.77    --  100.40 -94.00  90.00   80
 61  \w    131.00 159.00   1.00    0.77    --  100.40  77.00 120.00   28
 62  \w     75.00 142.00   1.00    0.77    --  100.40  77.00 150.00   67
 63  \w     36.00  61.00   1.00    0.77    --  100.40 -61.00  90.00   25
 64  \w     73.00 166.00   1.00    0.77    --  100.40  77.00  90.00   93
 65  \w     35.00  61.00   1.00    0.77    --  100.40 -61.00  30.00   26
 66  \w     77.00 151.00   1.00    0.77    --  100.40  77.00-120.00   74
 67  \w     75.00 167.00   1.00    0.77    --  100.40  77.00  30.00   92
 68  \w     36.00 117.00   1.00    0.77    --  100.40-125.00-120.00   81
;
_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      0.1918661000
_diffrn_orient_matrix_UB_12      0.0133801000
_diffrn_orient_matrix_UB_13      -0.0352748000
_diffrn_orient_matrix_UB_21      -0.0505418000
_diffrn_orient_matrix_UB_22      0.1154347000
_diffrn_orient_matrix_UB_23      -0.0106859000
_diffrn_orient_matrix_UB_31      0.1091302000
_diffrn_orient_matrix_UB_32      0.0299586000
_diffrn_orient_matrix_UB_33      0.0570777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47572
_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         74.643
_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  0.598
_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            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       tablet
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0245
_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^)+(0.0369P)^2^+0.3681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0640
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3972
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07477e3.cif
_cod_data_source_block           MM-XIV-8-F2(exp_402)
_cod_original_cell_volume        1980.257(18)
_cod_database_code               7124358
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H23O5
_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), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              88385
_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 1.186
_oxdiff_exptl_absorpt_empirical_full_min 0.837