Spiropiperidine Sultam and Lactam Templates: Diastereoselective Overman Rearrangement and Metathesis followed by NH Arylation.
Martinez-Alsina, Luis A; Murray, John C.; Buzon, Leanne M.; Bundesmann, Mark W.; Young, Joseph M.; O'Neill, Brian T; The Journal of organic chemistry 82 (2017) 12246–12256; doi:10.1021/acs.joc.7b02096

data_4033141
_publ_section_title
;
 Spiropiperidine Sultam and Lactam Templates: Diastereoselective Overman
 Rearrangement and Metathesis followed by NH Arylation.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12246
_journal_page_last               12256
_journal_paper_doi               10.1021/acs.joc.7b02096
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H23 Cl3 N2 O3'
_chemical_formula_weight         385.70
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
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_atom_sites_solution_hydrogens   geom
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_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6324(6)
_cell_length_b                   26.0858(14)
_cell_length_c                   6.4645(4)
_cell_measurement_reflns_used    5826
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      64.64
_cell_measurement_theta_min      3.39
_cell_volume                     1961.59(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6899
_diffrn_reflns_theta_full        51.09
_diffrn_reflns_theta_max         51.09
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    4.352
_exptl_absorpt_correction_T_max  0.5810
_exptl_absorpt_correction_T_min  0.1799
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0812
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1640P)^2^+1.0914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2214
_refine_ls_wR_factor_ref         0.2256
_reflns_number_gt                1902
_reflns_number_total             2094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02096_si_001.cif
_cod_data_source_block           i952
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033141.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               4033141