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_4035728
_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         'C29 H29 Br N2 O7'
_chemical_formula_sum            'C29 H29 Br N2 O7'
_chemical_formula_weight         597.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.564(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6471(3)
_cell_length_b                   9.8270(2)
_cell_length_c                   19.3981(3)
_cell_measurement_reflns_used    4433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3810
_cell_measurement_theta_min      4.3360
_cell_volume                     2702.39(9)
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -19.00  26.00   1.00    1.24    --  -33.50  57.00  30.00   45
  2  \w    -53.00  36.00   1.00    1.24    --  -33.50  37.00   0.00   89
  3  \w    -23.00  46.00   1.00    1.24    --   35.36 -57.00  90.00   69
  4  \w     52.00 104.00   1.00    4.95    --  108.00 -94.00   0.00   52
  5  \w     84.00 124.00   1.00    4.95    --  108.00 -45.00   0.00   40
  6  \w     66.00 100.00   1.00    4.95    --  108.00 -94.00 -90.00   34
  7  \w     61.00 119.00   1.00    4.95    --  108.00 -45.00-120.00   58
  8  \w    142.00 175.00   1.00    4.95    --  108.00  30.00-180.00   33
  9  \w    103.00 138.00   1.00    4.95    --  108.00 109.00 -87.00   35
 10  \w     94.00 173.00   1.00    4.95    --  108.00  45.00-120.00   79
 11  \w    124.00 170.00   1.00    4.95    --  108.00  61.00  90.00   46
 12  \w     62.00 109.00   1.00    4.95    --  108.00 -94.00-150.00   47
 13  \w     43.00  92.00   1.00    4.95    --  108.00 -94.00-180.00   49
 14  \w     68.00  95.00   1.00    1.24    --   35.36-178.00 -90.00   27
 15  \w     42.00  69.00   1.00    1.24    --   35.36 -99.00-150.00   27
 16  \w     41.00  75.00   1.00    4.95    --  108.00 -45.00   0.00   34
 17  \w     43.00 124.00   1.00    4.95    --  108.00 -45.00  90.00   81
 18  \w    -40.00  -8.00   1.00    1.24    --  -33.50 -77.00-120.00   32
 19  \w    -99.00 -44.00   1.00    1.24    --  -33.50 -77.00-120.00   55
;
_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      0.0653775000
_diffrn_orient_matrix_UB_12      0.1098484000
_diffrn_orient_matrix_UB_13      -0.0180563000
_diffrn_orient_matrix_UB_21      -0.0791836000
_diffrn_orient_matrix_UB_22      0.1063534000
_diffrn_orient_matrix_UB_23      -0.0074090000
_diffrn_orient_matrix_UB_31      0.0355369000
_diffrn_orient_matrix_UB_32      0.0347933000
_diffrn_orient_matrix_UB_33      0.0796940000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.333
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56142
_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    1.468
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00158(11)
_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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+1.1066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4345
_reflns_number_total             5160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02046_si_003.cif
_cod_data_source_block           zhang-u127c-1-597
_cod_database_code               4035728
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C29 H29 N2 O7 Br'
_chemical_oxdiff_usercomment     'Zhang's Zhang-U127c-1-597'
_shelx_estimated_absorpt_t_max   0.609
_shelx_estimated_absorpt_t_min   0.466
_reflns_odcompleteness_completeness 99.94
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              79035
_shelx_hkl_checksum              62357
_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 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.789