Total Synthesis and Structure Revision of (±)-Clavilactone D Through Selective Cyclization of an α,β-Dicarbonyl Peroxide.
Lv, Leiyang; Snider, Barry B.; Li, Zhiping; The Journal of organic chemistry 82 (2017) 5487–5491; doi:10.1021/acs.joc.7b00693

data_4032520
_publ_section_title
;
 Total Synthesis and Structure Revision of (+-)-Clavilactone D Through
 Selective Cyclization of an \a,\b-Dicarbonyl Peroxide.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5487
_journal_page_last               5491
_journal_paper_doi               10.1021/acs.joc.7b00693
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C9 H8 Br N O5 S0'
_chemical_formula_weight         290.07
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.739(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5498(9)
_cell_length_b                   4.0298(6)
_cell_length_c                   30.129(3)
_cell_measurement_reflns_used    2348
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.42
_cell_volume                     1030.9(2)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1860
_diffrn_reflns_av_sigmaI/netI    0.0947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9333
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    3.993
_exptl_absorpt_correction_T_max  0.5023
_exptl_absorpt_correction_T_min  0.3805
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.794
_refine_diff_density_min         -1.711
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_gt           0.0791
_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^)+(0.1210P)^2^+6.1089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2192
_refine_ls_wR_factor_ref         0.2303
_reflns_number_gt                1795
_reflns_number_total             2025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00693_si_002.cif
_cod_data_source_block           zzy
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/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 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4032520
_refine_ls_r_factor_ref          0.0866