Synthesis and orthogonal functionalization of oxazolo[5',4':4,5]pyrano[2,3-b]pyridine by intra- and intermolecular Pd-catalyzed direct C-H bond heteroarylation.
Théveau, Laure; Schneider, Cédric; Querolle, Olivier; Meerpoel, Lieven; Levacher, Vincent; Hoarau, Christophe; Organic & biomolecular chemistry 14 (2016) 3459–3468; doi:10.1039/c6ob00227g

data_7155012
_publ_section_title
;
 Synthesis and orthogonal functionalization of
 oxazolo[5',4':4,5]pyrano[2,3-b]pyridine by intra- and intermolecular
 Pd-catalyzed direct C-H bond heteroarylation.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3459
_journal_page_last               3468
_journal_paper_doi               10.1039/c6ob00227g
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C9 H5 Cl1 N2 O2'
_chemical_formula_sum            'C9 H5 Cl N2 O2'
_chemical_formula_weight         208.6
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2015-01-23T14:31:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-07-15 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;
_cell_angle_alpha                111.248(2)
_cell_angle_beta                 92.409(2)
_cell_angle_gamma                91.899(2)
_cell_formula_units_Z            2
_cell_length_a                   4.6985(7)
_cell_length_b                   9.6719(14)
_cell_length_c                   9.8461(14)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     416.09(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  SMART
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         Molybdene
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3322
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0445P)^2^+0.1630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                1492
_reflns_number_total             1668
_reflns_threshold_expression     >2\s(I)
_publcif_datablock.id            {a6ec464d-e451-4258-a5bc-d6c38dde2ec0}
_cod_data_source_file            c6ob00227g2.cif
_cod_data_source_block           sc874
_cod_depositor_comments
'Adding full bibliography for 7155012--7155013.cif.'
_cod_database_code               7155012