Partial reduction of 3-heteroatom substituted 2-furoic acids: the role of an ortho group in viability and stereoselectivity
Timothy J. Donohoe; Andrew A. Calabrese; Jean-Baptiste Guillermin; Daryl Walter; J. Chem. Soc., Perkin Trans. 1  (2002) 1748–1756; doi:10.1039/b203437a

data_7204432
_publ_section_title
;
 Partial reduction of 3-heteroatom substituted 2-furoic acids: the role
 of an ortho group in viability and stereoselectivity
;
_journal_issue                   15
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              1748
_journal_page_last               1756
_journal_paper_doi               10.1039/b203437a
_journal_year                    2002
_chemical_formula_sum            'C14 H25 N O3 Si'
_chemical_formula_weight         283.44
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1439(11)
_cell_length_b                   11.6771(15)
_cell_length_c                   15.438(2)
_cell_measurement_reflns_used    969
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      28.945
_cell_measurement_theta_min      2.187
_cell_volume                     1648.4(4)
_computing_cell_refinement       'SMART V5.06/SAINT V6.02a (Bruker AXS, 1999)'
_computing_data_collection       'SMART V5.06 (Bruker AXS, 1999)'
_computing_data_reduction        'SAINT V6.02a (Bruker AXS, 1999)'
_computing_molecular_graphics    'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL V5.10 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL V5.10 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(1)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker AXS 1K CCD area detector'
_diffrn_measurement_method       'narrow frame \w 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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15940
_diffrn_reflns_theta_max         29.45
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_number         'see text'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.152
_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   0.03(9)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0755P)^2^+0.0750P] 
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                3901
_reflns_number_total             4186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b203437a.txt
_cod_data_source_block           0572s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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)2(1)2(1)
_cod_original_formula_sum        'C14 H25 N1 O3 Si1'
_cod_database_code               7204432