Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium-zinc base and regioselectivity-computed CH acidity relationship.
Messaoud, Mohamed Yacine Ameur; Bentabed-Ababsa, Ghenia; Hedidi, Madani; Derdour, Aïcha; Chevallier, Floris; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Picot, Laurent; Thiéry, Valérie; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Beilstein journal of organic chemistry 11 (2015) 1475–1485; doi:10.3762/bjoc.11.160

data_1529453
_publ_section_title
;
 Deproto-metallation of N-arylated pyrroles and indoles using a mixed
 lithium-zinc base and regioselectivity-computed CH acidity relationship.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1475
_journal_page_last               1485
_journal_paper_doi               10.3762/bjoc.11.160
_journal_volume                  11
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27
_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             2014-10-28T15:05:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.562(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4222(6)
_cell_length_b                   5.4888(3)
_cell_length_c                   19.7338(12)
_cell_measurement_reflns_used    3354
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      3.33
_cell_measurement_wavelength     0.71073
_cell_volume                     1216.23(12)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.034
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10156
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.897
_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    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.2677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.101
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2281
_reflns_number_total             2777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-11-160-S2.cif
_cod_data_source_block           5d
_cod_depositor_comments
;Adding full bibliography for 1529449--1529453.cif.

 Adding full bibliography for 1529449--1529453.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1529453