Synthesis of 2-Unsubstituted Pyrrolidines and Piperidines from Donor-Acceptor Cyclopropanes and Cyclobutanes: 1,3,5-Triazinanes as Surrogates for Formylimines.
Garve, Lennart K. B.; Kreft, Alexander; Jones, Peter G.; Werz, Daniel B.; The Journal of organic chemistry 82 (2017) 9235–9242; doi:10.1021/acs.joc.7b01631

data_4032812
_publ_section_title
;
 Synthesis of 2-Unsubstituted Pyrrolidines and Piperidines from
 Donor-Acceptor Cyclopropanes and Cyclobutanes: 1,3,5-Triazinanes as
 Surrogates for Formylimines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9235
_journal_page_last               9242
_journal_paper_doi               10.1021/acs.joc.7b01631
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C20 H20 Br N O4'
_chemical_formula_weight         418.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.1564(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3569(2)
_cell_length_b                   8.15707(12)
_cell_length_c                   17.6178(3)
_cell_measurement_reflns_used    25264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9600
_cell_measurement_theta_min      3.4460
_cell_volume                     1834.10(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            54952
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.20
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+1.3205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                3445
_reflns_number_total             3838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01631_si_002.cif
_cod_data_source_block           varge
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032812