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_7131746
_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_formula_moiety         'C32 H48 N4 O14'
_chemical_formula_sum            'C32 H48 N4 O14'
_chemical_formula_weight         712.74
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-03-17
_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                102.528(7)
_cell_angle_beta                 110.036(8)
_cell_angle_gamma                102.007(8)
_cell_formula_units_Z            1
_cell_length_a                   9.4928(9)
_cell_length_b                   9.8026(9)
_cell_length_c                   11.3802(8)
_cell_measurement_reflns_used    2550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1960
_cell_measurement_theta_min      4.3290
_cell_volume                     924.02(16)
_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 0.995
_diffrn_measured_fraction_theta_max 0.955
_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 -35.00   1.00    1.00    --  -33.50 178.00  90.00   73
  2  \w   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  30.00   73
  3  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -30.00   93
  4  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00-120.00   93
  5  \w    -52.00  35.00   1.00    1.00    --  -33.50  57.00 120.00   87
  6  \w    -62.00  36.00   1.00    1.00    --  -33.50  77.00-150.00   98
  7  \w      1.00  76.00   1.00    1.00    --   36.47 -99.00-150.00   75
  8  \w     61.00 110.00   1.00    1.00    --   36.47 178.00  60.00   49
  9  \w      1.00  76.00   1.00    1.00    --   36.47 -99.00  60.00   75
 10  \w     40.00 109.00   1.00    1.00    --  108.00-111.00 -90.00   69
 11  \w     66.00 104.00   1.00    1.00    --  108.00 178.00  30.00   38
 12  \w     88.00 178.00   1.00    1.00    --  108.00  45.00 150.00   90
 13  \w     49.00 128.00   1.00    1.00    --  108.00 -45.00  60.00   79
 14  \w     88.00 176.00   1.00    1.00    --  108.00  45.00  90.00   88
 15  \w     42.00 103.00   1.00    1.00    --  108.00 -94.00  30.00   61
 16  \w     95.00 136.00   1.00    1.00    --  108.00 -77.00  90.00   41
 17  \w    128.00 169.00   1.00    1.00    --  108.00  45.00   0.00   41
 18  \w     39.00  99.00   1.00    1.00    --  108.00 -94.00  90.00   60
 19  \w    110.00 176.00   1.00    1.00    --  108.00 111.00  30.00   66
 20  \w    133.00 175.00   1.00    1.00    --  108.00  74.00 123.00   42
 21  \w    126.00 177.00   1.00    1.00    --  108.00  77.00-180.00   51
 22  \w     80.00 106.00   1.00    1.00    --  108.00 -94.00 120.00   26
 23  \w     38.00 100.00   1.00    1.00    --  108.00 -94.00 -30.00   62
 24  \w    153.00 178.00   1.00    1.00    --  108.00  45.00-120.00   25
 25  \w     88.00 133.00   1.00    1.00    --  108.00  45.00-120.00   45
;
_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      -0.0054249000
_diffrn_orient_matrix_UB_12      0.1529011000
_diffrn_orient_matrix_UB_13      0.0649778000
_diffrn_orient_matrix_UB_21      0.1679945000
_diffrn_orient_matrix_UB_22      0.0353919000
_diffrn_orient_matrix_UB_23      0.1048260000
_diffrn_orient_matrix_UB_31      0.0686483000
_diffrn_orient_matrix_UB_32      0.0632519000
_diffrn_orient_matrix_UB_33      -0.0884148000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6573
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.583
_diffrn_reflns_theta_min         4.355
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91030
_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    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0076(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0664P)^2^+0.2851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2472
_reflns_number_total             3435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02172f2.cif
_cod_data_source_block           20230339
_cod_original_cell_volume        924.02(15)
_cod_database_code               7131746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N3O4
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.883
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Restrained distances
 C9-C10
 1.56 with sigma of 0.02
 C10A-C9A
 1.56 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
4. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C11(H11A,H11B)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              47145
_shelx_hkl_checksum              62272
_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 1.848
_oxdiff_exptl_absorpt_empirical_full_min 0.890