N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides
Chevallier, Floris; Halauko, Yury S.; Pecceu, Christelle; Nassar, Ibrahim F.; Dam, To Uyen; Roisnel, Thierry; Matulis, Vadim E.; Ivashkevich, Oleg A.; Mongin, Florence; Organic & Biomolecular Chemistry 9 (2011) 4671–; doi:10.1039/c1ob05267e

data_7151883
_publ_section_title
;
 N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative
 metallation using a combination of lithium and zinc amides
;
_journal_issue                   12
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4671
_journal_paper_doi               10.1039/c1ob05267e
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C8 H3 Cl I3 N3'
_chemical_formula_sum            'C8 H3 Cl I3 N3'
_chemical_formula_weight         557.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-02-24T15:25:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.696(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8807(5)
_cell_length_b                   7.3931(3)
_cell_length_c                   14.3980(6)
_cell_measurement_reflns_used    5293
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.28
_cell_measurement_wavelength     0.71073
_cell_volume                     1263.25(9)
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10351
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.1
_exptl_absorpt_coefficient_mu    7.606
_exptl_absorpt_correction_T_max  0.088
_exptl_absorpt_correction_T_min  0.029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.93
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.32
_refine_diff_density_max         1.963
_refine_diff_density_min         -1.499
_refine_diff_density_rms         0.256
_refine_ls_extinction_coef       0.0063(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+4.4298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                2561
_reflns_number_total             2882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05267e.txt
_cod_data_source_block           9m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151883