Synthesis of a 7-Azaindole by Chichibabin Cyclization: Reversible Base-Mediated Dimerization of 3-Picolines
Yun Ma; Sean Breslin; Ivan Keresztes; Emil Lobkovsky; David B. Collum; Journal of Organic Chemistry 73 (2008) 9610–9618; doi:10.1021/jo801410s

data_4023920
_publ_section_title
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 Synthesis of a 7-Azaindole by Chichibabin Cyclization:
 Reversible Base-Mediated Dimerization of 3-Picolines
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9610
_journal_page_last               9618
_journal_paper_doi               10.1021/jo801410s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H10 F2 N2'
_chemical_formula_sum            'C12 H10 F2 N2'
_chemical_formula_weight         220.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.050(4)
_cell_angle_beta                 95.711(4)
_cell_angle_gamma                94.074(4)
_cell_formula_units_Z            4
_cell_length_a                   7.3370(8)
_cell_length_b                   10.6664(11)
_cell_length_c                   13.1655(14)
_cell_measurement_reflns_used    7542
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.80
_cell_volume                     1021.67(19)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21945
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.513
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.513
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.051
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2301
_reflns_number_gt                3596
_reflns_number_total             5007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801410s_si_002.cif
_cod_data_source_block           ym1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
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_cod_database_code               4023920