Flexible strategy for differentially 3,5-disubstituted 4-oxypyridin-2(1H)-ones based on site-selective Pd-catalyzed cross-coupling reactions.
Conreaux, David; Bossharth, Emmanuel; Monteiro, Nuno; Desbordes, Philippe; Vors, Jean-Pierre; Balme, Geneviève; Organic letters 9 (2007) 271–274; doi:10.1021/ol062721u

data_1505259
_publ_section_title
;
 Flexible strategy for differentially 3,5-disubstituted
 4-oxypyridin-2(1H)-ones based on site-selective Pd-catalyzed
 cross-coupling reactions.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              271
_journal_page_last               274
_journal_paper_doi               10.1021/ol062721u
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C14 H14 I1 N1 O3'
_chemical_formula_sum            'C14 H14 I N O3'
_chemical_formula_weight         371.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-03-09
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                90
_cell_angle_beta                 126.758(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.296(5)
_cell_length_b                   26.087(5)
_cell_length_c                   9.364(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1427.9(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10054
_diffrn_reflns_theta_full        27.878
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.825
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.246
_exptl_absorpt_correction_T_max  0.60
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000572
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.567 0.166 0.309 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0542
_refine_ls_wR_factor_gt          0.0308
_refine_ls_wR_factor_ref         0.0308
_reflns_limit_h_max              7
_reflns_limit_h_min              -9
_reflns_limit_k_max              34
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1767
_reflns_number_total             3321
_reflns_threshold_expression     I>3.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.3130(5)
_oxford_structure_analysis_title 'new in P 21/c'
_cod_data_source_file            ol062721usi20061107_083715.cif
_cod_data_source_block           CRYSTALS_cif
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C14 H14 I1 N1 O3'
_cod_database_code               1505259