Catalytic asymmetric interrupted Attanasi reaction: access to fused 2,3-dihydropyrroles with vicinal quaternary carbons.
Chen, Yun-Xuan; Han, Tian-Jiao; Xiao, Xiao; Wang, Min-Can; Mei, Guang-Jian; Chemical communications (Cambridge, England) 59 (2023) 8103–8106; doi:10.1039/d3cc02172f

data_7131745
_publ_section_title
;
 Catalytic asymmetric interrupted Attanasi reaction: access to fused
 2,3-dihydropyrroles with vicinal quaternary carbons.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8103
_journal_page_last               8106
_journal_paper_doi               10.1039/d3cc02172f
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 N2 O7'
_chemical_formula_sum            'C15 H22 N2 O7'
_chemical_formula_weight         342.34
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-01 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.24888(18)
_cell_length_b                   8.64551(16)
_cell_length_c                   24.3498(5)
_cell_measurement_reflns_used    7994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0810
_cell_measurement_theta_min      5.4190
_cell_volume                     1736.52(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -89.00 -35.00   1.00    1.00    --  -33.50 178.00-180.00   54
  2  \w   -103.00 -11.00   1.00    1.00    --  -33.50 -37.00 150.00   92
  3  \w    -90.00 -40.00   1.00    1.00    --  -33.50 178.00   0.00   50
  4  \w    -69.00 -43.00   1.00    1.00    --  -33.50 -65.00  60.89   26
  5  \w    -53.00  -4.00   1.00    1.00    --  -33.50 -19.00   0.00   49
  6  \w   -105.00 -35.00   1.00    1.00    --  -33.50 178.00 -60.00   70
  7  \w    -88.00 -27.00   1.00    1.00    --  -33.50 -37.00  90.00   61
  8  \w   -105.00 -36.00   1.00    1.00    --  -33.50 178.00-120.00   69
  9  \w     61.00  87.00   1.00    1.00    --   36.47 178.00 -90.00   26
 10  \w     -2.00  24.00   1.00    1.00    --   36.47  95.00 139.57   26
 11  \w     68.00 108.00   1.00    1.00    --   36.47 178.00   0.00   40
 12  \w     88.00 114.00   1.00    5.00    --  108.00  45.00 150.00   26
 13  \w     88.00 119.00   1.00    5.00    --  108.00  45.00  60.00   31
 14  \w    108.00 144.00   1.00    5.00    --  108.00 111.00-150.00   36
 15  \w    140.00 166.00   1.00    5.00    --  108.00  30.00 150.00   26
 16  \w     85.00 119.00   1.00    5.00    --  108.00  30.00 150.00   34
 17  \w     88.00 114.00   1.00    5.00    --  108.00  61.00 150.00   26
 18  \w     53.00 101.00   1.00    5.00    --  108.00-111.00  30.00   48
 19  \w     88.00 114.00   1.00    5.00    --  108.00  61.00  60.00   26
 20  \w     37.00  99.00   1.00    5.00    --  108.00 -30.00 -30.00   62
 21  \w    122.00 178.00   1.00    5.00    --  108.00  30.00-180.00   56
 22  \w    122.00 176.00   1.00    5.00    --  108.00  61.00  60.00   54
 23  \w     53.00 104.00   1.00    5.00    --  108.00 -77.00-120.00   51
 24  \w     88.00 114.00   1.00    5.00    --  108.00  61.00 120.00   26
 25  \w     47.00 106.00   1.00    5.00    --  108.00 -94.00  30.00   59
 26  \w     88.00 114.00   1.00    5.00    --  108.00  45.00  90.00   26
 27  \w     83.00 108.00   1.00    5.00    --  108.00  30.00  60.00   25
 28  \w     88.00 132.00   1.00    5.00    --  108.00  45.00 120.00   44
 29  \w     52.00  78.00   1.00    5.00    --  108.00 -45.00   0.00   26
 30  \w    148.00 175.00   1.00    5.00    --  108.00 111.00-150.00   27
 31  \w    118.00 144.00   1.00    5.00    --  108.00 -15.00 150.00   26
 32  \w     82.00 117.00   1.00    5.00    --  108.00  30.00-180.00   35
 33  \w     56.00  98.00   1.00    5.00    --  108.00-111.00   0.00   42
 34  \w     93.00 118.00   1.00    5.00    --  108.00 -61.00-150.00   25
 35  \w     85.00 128.00   1.00    5.00    --  108.00 -45.00-150.00   43
 36  \w     40.00  66.00   1.00    5.00    --  108.00 -61.00-150.00   26
 37  \w    104.00 173.00   1.00    5.00    --  108.00  77.00 120.00   69
 38  \w     47.00  94.00   1.00    5.00    --  108.00 -15.00 150.00   47
 39  \w    152.00 177.00   1.00    5.00    --  108.00  77.00 -30.00   25
 40  \w    128.00 174.00   1.00    5.00    --  108.00  61.00  90.00   46
 41  \w     82.00 113.00   1.00    5.00    --  108.00  30.00  90.00   31
 42  \w     88.00 114.00   1.00    5.00    --  108.00  30.00 120.00   26
 43  \w     69.00  95.00   1.00    5.00    --  108.00 178.00  30.00   26
 44  \w     82.00 108.00   1.00    5.00    --  108.00  30.00-150.00   26
 45  \w    115.00 141.00   1.00    5.00    --  108.00  30.00-150.00   26
 46  \w     84.00 171.00   1.00    5.00    --  108.00  30.00-120.00   87
 47  \w    119.00 145.00   1.00    5.00    --  108.00  77.00 -30.00   26
 48  \w     88.00 114.00   1.00    5.00    --  108.00  61.00  90.00   26
 49  \w     56.00 101.00   1.00    5.00    --  108.00 -82.00  33.50   45
 50  \w     39.00  64.00   1.00    5.00    --  108.00 -45.00-150.00   25
 51  \w     40.00 108.00   1.00    5.00    --  108.00-111.00 -60.00   68
 52  \w    122.00 148.00   1.00    5.00    --  108.00 111.00-120.00   26
 53  \w    117.00 163.00   1.00    5.00    --  108.00  77.00  30.00   46
 54  \w     88.00 114.00   1.00    5.00    --  108.00  61.00-180.00   26
 55  \w     67.00 105.00   1.00    5.00    --  108.00 -82.00 179.36   38
 56  \w     70.00 103.00   1.00    5.00    --  108.00 -66.00  25.82   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268263000
_diffrn_orient_matrix_UB_12      0.0018154000
_diffrn_orient_matrix_UB_13      0.0626137000
_diffrn_orient_matrix_UB_21      -0.1034292000
_diffrn_orient_matrix_UB_22      0.1477928000
_diffrn_orient_matrix_UB_23      0.0045517000
_diffrn_orient_matrix_UB_31      -0.1531795000
_diffrn_orient_matrix_UB_32      -0.0994984000
_diffrn_orient_matrix_UB_33      0.0078883000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.400
_diffrn_reflns_theta_min         3.630
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0766P)^2^+0.1178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3117
_reflns_number_total             3330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02172f2.cif
_cod_data_source_block           20230358_auto
_cod_database_code               7131745
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N3O4
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.894
_reflns_odcompleteness_completeness 94.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-O1
 0.9 with sigma of 0.02
 C12A-C13A
 1.54 with sigma of 0.02
 C12-C13
 1.65 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(O5) = Uanis(O5A)
4. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=
 Sof(O5A)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(O5)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C12(H12A,H12B), C12A(H12C,H12D)
5.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C13A(H13D,H13E,
 H13F), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              15372
_shelx_hkl_checksum              83682
_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 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.929