Dearomatizing cyclization of arylsulfonylalkoxymethyl lithiums: a route to the podophyllotoxin skeleton.
Clayden, Jonathan; Kenworthy, Martin N.; Helliwell, Madeleine; Organic letters 5 (2003) 831–834; doi:10.1021/ol0340585

data_1507264
_publ_section_title
;
 Dearomatizing cyclization of arylsulfonylalkoxymethyl lithiums: a route
 to the podophyllotoxin skeleton.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              831
_journal_page_last               834
_journal_paper_doi               10.1021/ol0340585
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C18 H16 O4 S'
_chemical_formula_weight         328.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.02(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.32(2)
_cell_length_b                   5.801(5)
_cell_length_c                   11.58(2)
_cell_measurement_reflns_used    12404
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      1.84
_cell_volume                     744(2)
_computing_cell_refinement       'DENZO (Otwinowski, Z. 1988)'
_computing_data_collection       'MSC RAXIS11 Control'
_computing_data_reduction        'DENZO (Otwinowski, Z. 1988)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.807
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measurement_device       'Rigaku RAXIS'
_diffrn_measurement_method       '60 x 5 degree phi scans'
_diffrn_radiation_detector       'image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12404
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0501P)^2^+0.0815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                1898
_reflns_number_total             1926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0340585si20030113_023233.cif
_cod_data_source_block           s1005
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.0815P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.0815P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        743.4(19)
_cod_original_sg_symbol_H-M      'P 21       '
_cod_database_code               1507264