One-Pot Double [3 + 2] Cycloadditions for Diastereoselective Synthesis of Pyrrolidine-Based Polycyclic Systems.
Zhang, Xiaofeng; Qiu, Weiqi; Ma, Xiaoming; Evans, Jason; Kaur, Manpreet; Jasinski, Jerry P.; Zhang, Wei; The Journal of organic chemistry 83 (2018) 13536–13542; doi:10.1021/acs.joc.8b02046

data_4035727
_publ_section_title
;
 One-Pot Double [3 + 2] Cycloadditions for Diastereoselective Synthesis of
 Pyrrolidine-Based Polycyclic Systems.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13536
_journal_page_last               13542
_journal_paper_doi               10.1021/acs.joc.8b02046
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C27 H25 Br N2 O6'
_chemical_formula_sum            'C27 H25 Br N2 O6'
_chemical_formula_weight         553.40
_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_creation_date             2018-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                97.508(6)
_cell_angle_beta                 91.047(5)
_cell_angle_gamma                93.474(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1480(3)
_cell_length_b                   9.3553(7)
_cell_length_c                   21.4639(14)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3530
_cell_measurement_theta_min      4.1520
_cell_volume                     1221.26(14)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015a)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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     34.00  99.00   1.00    1.04    --   35.48  57.00 -60.00   65
  2  \w     95.00 142.00   1.00    4.16    --  108.00  61.00 -90.00   47
  3  \w    110.00 136.00   1.00    4.16    --  108.00  61.00 -30.00   26
  4  \w    108.00 175.00   1.00    4.16    --  108.00  61.00 -60.00   67
  5  \w     92.00 131.00   1.00    4.16    --  108.00 -77.00   0.00   39
  6  \w     79.00 109.00   1.00    4.16    --  108.00 -94.00-120.00   30
  7  \w     81.00 114.00   1.00    4.16    --  108.00-111.00-180.00   33
  8  \w     53.00  95.00   1.00    1.04    --   35.48-178.00-120.00   42
  9  \w     38.00  74.00   1.00    1.04    --   35.48 -99.00-180.00   36
 10  \w     42.00  74.00   1.00    1.04    --   35.48 -99.00 -60.00   32
 11  \w     21.00  72.00   1.00    1.04    --   35.48 -99.00  60.00   51
 12  \w     52.00 126.00   1.00    4.16    --  108.00 -30.00 120.00   74
 13  \w     67.00 102.00   1.00    4.16    --  108.00-111.00   0.00   35
 14  \w     71.00 104.00   1.00    4.16    --  108.00 -61.00   0.00   33
 15  \w     44.00 116.00   1.00    4.16    --  108.00 -45.00-120.00   72
 16  \w     42.00  82.00   1.00    4.16    --  108.00 -77.00   0.00   40
 17  \w     40.00 125.00   1.00    4.16    --  108.00 -30.00   0.00   85
 18  \w     40.00  80.00   1.00    4.16    --  108.00 -94.00 150.00   40
 19  \w     41.00 126.00   1.00    4.16    --  108.00 -61.00 150.00   85
 20  \w     38.00 115.00   1.00    4.16    --  108.00-111.00  60.00   77
 21  \w     37.00 130.00   1.00    4.16    --  108.00 -15.00 -60.00   93
 22  \w    -63.00  38.00   1.00    1.04    --  -33.50  19.00  60.00  101
 23  \w    -72.00 -47.00   1.00    1.04    --  -33.50 -77.00   0.00   25
 24  \w    -96.00 -17.00   1.00    1.04    --  -33.50 -57.00-120.00   79
 25  \w    -80.00 -52.00   1.00    1.04    --  -33.50-178.00  90.00   28
 26  \w    -79.00 -33.00   1.00    1.04    --  -33.50 178.00   0.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, Oxford diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1029744000
_diffrn_orient_matrix_UB_12      -0.0233548000
_diffrn_orient_matrix_UB_13      -0.0651376000
_diffrn_orient_matrix_UB_21      0.1037700000
_diffrn_orient_matrix_UB_22      0.1556741000
_diffrn_orient_matrix_UB_23      0.0108018000
_diffrn_orient_matrix_UB_31      0.2040873000
_diffrn_orient_matrix_UB_32      -0.0541884000
_diffrn_orient_matrix_UB_33      0.0297295000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8057
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.192
_diffrn_reflns_theta_min         4.156
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.505
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0590P)^2^+0.2989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3827
_reflns_number_total             4658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02046_si_002.cif
_cod_data_source_block           zhang-u127c-22-553
_cod_original_cell_volume        1221.27(13)
_cod_database_code               4035727
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C27 H25 N2 O6 Br'
_chemical_oxdiff_usercomment     'Zhang's Zhang-U127c-22-553'
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.565
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C4(H4), C5(H5), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              12662
_shelx_hkl_checksum              11399
_olex2_exptl_crystal_mounting_method 'polymer 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 2.080
_oxdiff_exptl_absorpt_empirical_full_min 0.731