Stereocontrolled Approach to Phenyl Cyclitols from (SR)-[(p-Tolylsulfinyl)methyl]-p-quinol
Estíbaliz Merino; Rosanne P. A. Melo; Montserrat Ortega-Guerra; María Ribagorda; M. Carmen Carreño; Journal of Organic Chemistry 74 (2009) 2824–2831; doi:10.1021/jo900109p

data_4024459
_publ_section_title
;
Stereocontrolled Approach to Phenyl Cyclitols from
(SR)-[(p-Tolylsulfinyl)methyl]-p-quinol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2824
_journal_page_last               2831
_journal_paper_doi               10.1021/jo900109p
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C21 H22 O3 S'
_chemical_formula_weight         354.45
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.6190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.36750(10)
_cell_length_b                   32.5836(6)
_cell_length_c                   7.58820(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1784.29(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9412
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         67.68
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     623
_refine_ls_number_reflns         5024
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0743
_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^)+(0.1547P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.1941
_reflns_number_gt                4454
_reflns_number_total             5024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900109p_si_001.cif
_cod_data_source_block           crist2_m
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024459