Rhodium-Catalyzed/Copper-Mediated Tandem C(sp(2))-H Alkynylation and Annulation: Synthesis of 11-Acylated Imidazo[1,2-a:3,4-a']dipyridin-5-ium-4-olates from 2H-[1,2'-Bipyridin]-2-ones and Propargyl Alcohols.
Li, Ting; Wang, Zhiqiang; Xu, Kun; Liu, Wenmin; Zhang, Xu; Mao, Wutao; Guo, Yongming; Ge, Xiaolin; Pan, Fei; Organic letters 18 (2016) 1064–; doi:10.1021/acs.orglett.6b00177

data_1542443
_publ_section_title
;
 Rhodium-Catalyzed/Copper-Mediated Tandem C(sp(2))-H Alkynylation and
 Annulation: Synthesis of 11-Acylated
 Imidazo[1,2-a:3,4-a']dipyridin-5-ium-4-olates from
 2H-[1,2'-Bipyridin]-2-ones and Propargyl Alcohols.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1064
_journal_paper_doi               10.1021/acs.orglett.6b00177
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H11 F3 N2 O2'
_chemical_formula_sum            'C19 H11 F3 N2 O2'
_chemical_formula_weight         356.30
_chemical_name_systematic
; 
 ? 
;
_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                103.84(3)
_cell_angle_beta                 91.68(3)
_cell_angle_gamma                98.51(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5256(15)
_cell_length_b                   7.9629(16)
_cell_length_c                   13.641(3)
_cell_measurement_reflns_used    509
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      16.88
_cell_measurement_theta_min      3.12
_cell_volume                     783.2(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6630
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0667
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2539
_reflns_number_gt                2155
_reflns_number_total             3075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00177_si_003.cif
_cod_data_source_block           p
_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/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1542443--1542444.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1542443