Copper-mediated synthesis of pyrazolo[1,5-a]pyridines through oxidative linkage of C-C/N-N bonds.
Mohan, Darapaneni Chandra; Ravi, Chitrakar; Rao, Sadu Nageswara; Adimurthy, Subbarayappa; Organic & biomolecular chemistry 13 (2015) 3556–3560; doi:10.1039/c5ob00018a

data_7154337
_publ_section_title
;
 Copper-mediated synthesis of pyrazolo[1,5-a]pyridines through oxidative
 linkage of C-C/N-N bonds.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3556
_journal_page_last               3560
_journal_paper_doi               10.1039/c5ob00018a
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        Synthesis
_chemical_formula_moiety         C16H14N2O2
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_chemical_name_systematic
'ethyl 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate'
_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_block_doi                 10.5517/cc13rbt0
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-21 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                78.727(2)
_cell_angle_beta                 85.961(2)
_cell_angle_gamma                86.336(2)
_cell_formula_units_Z            2
_cell_length_a                   3.8783(5)
_cell_length_b                   11.1617(14)
_cell_length_c                   15.3358(19)
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.71
_cell_volume                     648.58(14)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5041
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             280
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane-Ethyl acetate'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0191P)^2^+0.5609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2350
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00018a2.cif
_cod_data_source_block           cm152m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7154337.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154337