Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization.
Leisering, Stefan; Riaño, Iker; Depken, Christian; Gross, Leona J.; Weber, Manuela; Lentz, Dieter; Zimmer, Reinhold; Stark, Christian B. W.; Breder, Alexander; Christmann, Mathias; Organic letters 19 (2017) 1478–1481; doi:10.1021/acs.orglett.7b00484

data_1545394
_publ_section_title
;
 Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative
 Epoxidation and a Selenium-Catalyzed Oxidative Cyclization.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1478
_journal_page_last               1481
_journal_paper_doi               10.1021/acs.orglett.7b00484
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C17 H22 N2 O7'
_chemical_formula_weight         366.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 93.062(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7132(6)
_cell_length_b                   5.9764(3)
_cell_length_c                   28.5202(17)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.1
_cell_volume                     1823.44(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            22869
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.379
_diffrn_reflns_theta_min         3.103
_diffrn_source                   'Incoatec Microfocus Source'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Burker-aXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6635
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0391P)^2^+0.1487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5186
_reflns_number_total             6635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00484_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1545392--1545395.cif.'
_cod_database_code               1545394
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.667
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              22715
_shelx_hkl_checksum              64105