Stereocontrolled construction of either stereoisomer of 12-oxatricyclo[6.3.1.0(2,7)]dodecanes using Prins-pinacol reactions.
Overman, Larry E.; Velthuisen, Emile J.; Organic letters 6 (2004) 3853–3856; doi:10.1021/ol0482745

data_1506963
_publ_section_title
;
 Stereocontrolled construction of either stereoisomer of
 12-oxatricyclo[6.3.1.0(2,7)]dodecanes using Prins-pinacol reactions.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              3853
_journal_page_last               3856
_journal_paper_doi               10.1021/ol0482745
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C23 H32 N2 O3 S3'
_chemical_formula_weight         480.69
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.8190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            32
_cell_length_a                   61.439(2)
_cell_length_b                   10.1168(4)
_cell_length_c                   31.4020(12)
_cell_measurement_temperature    163(2)
_cell_volume                     19337.0(12)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       76
_diffrn_reflns_limit_h_min       -76
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            90358
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         0.67
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.9123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             8192
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1133
_refine_ls_number_reflns         19720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0386P)^2^+43.5873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                12962
_reflns_number_total             19720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0482745si20040830_022042.cif
_cod_data_source_block           leo149
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        19336.9(13)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1506963