Deprotonative Metalation of Five-Membered Aromatic Heterocycles Using Mixed Lithium-Zinc Species
Jean-Martial L'Helgoual'ch; Anne Seggio; Floris Chevallier; Mitsuhiro Yonehara; Erwann Jeanneau; Masanobu Uchiyama; Florence Mongin; Journal of Organic Chemistry 73 (2008) 177–183; doi:10.1021/jo7020345

data_4023175
_publ_contact_author_address
;     Synth\`ese et Electrosynth\`ese Organique
 UMR 6510 CNRS, Universit\'e de Rennes 1
 Avenue du G\'en\'eral Leclerc
 35042 Rennes Cedex, France.
;
_publ_contact_author_email       florence.mongin@univ-rennes1.fr
_publ_contact_author_name        'MONGIN, Florence'
_publ_section_title
;
 Deprotonative Metalation of Five-Membered Aromatic Heterocycles
 Using Mixed Lithium-Zinc Species
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              177
_journal_page_last               183
_journal_paper_doi               10.1021/jo7020345
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C3 H1 I2 N1 S1'
_chemical_formula_sum            'C3 H I2 N S'
_chemical_formula_weight         336.92
_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             07-08-28
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 117.33(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.363(4)
_cell_length_b                   13.529(6)
_cell_length_c                   7.998(1)
_cell_measurement_reflns_used    1263
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.730
_cell_volume                     707.8(5)
_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      295
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.968
_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  0.079
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3390
_diffrn_reflns_theta_full        26.996
_diffrn_reflns_theta_max         28.416
_diffrn_reflns_theta_min         3.011
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.069
_exptl_absorpt_correction_T_max  0.48
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'DIFABS (Walker & Stuart, 1983)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    3.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.11
_refine_diff_density_min         -1.52
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000248
_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: 
 2.31 0.631 1.53 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0835
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0637
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1069
_reflns_number_total             1720
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0549
_oxford_refine_ls_scale          0.725(4)
_oxford_reflns_number_all        1715
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            jo7020345-File003.cif
_cod_data_source_block           jml016
_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      'P 21/c'
_cod_original_formula_sum        'C3 H1 I2 N S'
_cod_database_code               4023175