Expedient Two-Step Synthesis of Phenolic Cyclitols from Benzene
Crich, David; Grant, Daniel; Wink, Donald J.; The Journal of Organic Chemistry 71 (2006) 4521–4524; doi:10.1021/jo0603734

data_4028894
_publ_section_title
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 Expedient Two-Step Synthesis of Phenolic Cyclitols from Benzene
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_journal_issue                   12
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              4521
_journal_page_last               4524
_journal_paper_doi               10.1021/jo0603734
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C16 H21 O6'
_chemical_formula_weight         320.33
_chemical_name_systematic
; 
 (1R,2S,3r,4R,5S)-3-(2-Hydroxyphenyl)-1,2,4,5-cyclohexanetetraol  
;
_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           SHELXL-97
_audit_update_record
;
2006-02-27  Received for J. Org. Chem. manuscript jo0603734
            Minor syntax errors corrected (JOC/pH)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.194(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   19.799(3)
_cell_length_b                   6.5410(11)
_cell_length_c                   17.571(3)
_cell_measurement_reflns_used    1401
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.10
_cell_measurement_theta_min      2.73
_cell_volume                     2173.8(6)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2910
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0402P)^2^+7.8894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                1423
_reflns_number_total             1548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0603734sup2.cif
_cod_data_source_block           Compound13
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4028894
_cod_duplicate_entry 4021737