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_1545392
_publ_contact_author
;
      Prof. Dr.Christian M\"uller
      Freie Universit\"at Berlin
      Institut f\"ur Chemie und Biochemie
      Anorganische Chemie      
      Fabeckstr. 34-36
      14195 Berlin
      Germany
;
_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_absolute_configuration ad
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 124.5300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6466(5)
_cell_length_b                   5.6440(2)
_cell_length_c                   13.4475(4)
_cell_measurement_reflns_used    2935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.45
_cell_volume                     1040.86(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  'X-STEP32, Microsoft Word'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6654
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.434
_diffrn_reflns_theta_min         2.452
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       platelet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.7037
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0385P)^2^+0.2162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                1922
_reflns_number_total             2118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00484_si_002.cif
_cod_data_source_block           IC0009b_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
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 1545392--1545395.cif.
;
_cod_database_code               1545392
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              49871
_shelx_hkl_checksum              12349