Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis.
Cho, Inhee; Meimetis, Labros; Belding, Lee; Katz, Michael J.; Dudding, Travis; Britton, Robert; Beilstein journal of organic chemistry 7 (2011) 1315–1322; doi:10.3762/bjoc.7.154

data_4029732
_publ_section_title
;
 Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to
 hydrobenzoin derivatives useful for asymmetric synthesis.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1315
_journal_page_last               1322
_journal_paper_doi               10.3762/bjoc.7.154
_journal_volume                  7
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 O2 Si1'
_chemical_formula_sum            'C18 H22 O2 Si'
_chemical_formula_weight         298.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.82150(10)
_cell_length_b                   13.4340(3)
_cell_length_c                   17.9267(4)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.68
_cell_measurement_theta_min      2.73
_cell_volume                     1642.80(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Ortep-3
_computing_structure_refinement  Crystals
_computing_structure_solution    'Sir 9x'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Apex II CCD (Bruker AXS)'
_diffrn_measurement_method       '0.5 degree \f & \w scans'
_diffrn_radiation_monochromator  'graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            63558
_diffrn_reflns_theta_full        33.219
_diffrn_reflns_theta_max         34.968
_diffrn_reflns_theta_min         1.894
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 3104 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.7515
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.000938
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0573
_refine_ls_wR_factor_gt          0.0342
_refine_ls_wR_factor_ref         0.0342
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                4784
_reflns_number_total             7111
_reflns_threshold_expression     I>2.5\s(I)
_oxford_diffrn_Wilson_B_factor   1.76
_oxford_diffrn_Wilson_scale      19.75
_oxford_refine_ls_scale          0.2346(2)
_cod_data_source_file            1860-5397-7-154-S2.cif
_cod_data_source_block           C18_H22_O2_Si1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C18 H22 O2 Si1'
_cod_database_code               4029732