Synthesis of Naphtho[1',2':4,5]imidazo[1,2-a]pyridines and Imidazo[5,1,2-cd]indolizines Through Pd-Catalyzed Cycloaromatization of 2-Phenylimidazo[1,2-a]pyridines with Alkynes.
Li, Peiyuan; Zhang, Xinying; Fan, Xuesen; The Journal of organic chemistry 80 (2015) 7508–7518; doi:10.1021/acs.joc.5b01092

data_4031318
_publ_section_title
;
 Synthesis of Naphtho[1',2':4,5]imidazo[1,2-a]pyridines and
 Imidazo[5,1,2-cd]indolizines Through Pd-Catalyzed Cycloaromatization of
 2-Phenylimidazo[1,2-a]pyridines with Alkynes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7508
_journal_page_last               7518
_journal_paper_doi               10.1021/acs.joc.5b01092
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 100.558(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5565(16)
_cell_length_b                   9.6319(15)
_cell_length_c                   20.534(3)
_cell_measurement_reflns_used    1357
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.72
_cell_measurement_theta_min      2.54
_cell_volume                     2052.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10591
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0500P)^2^+0.4384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                2076
_reflns_number_total             3827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01092_si_002.cif
_cod_data_source_block           c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031317--4031318.cif.
;
_cod_original_cell_volume        2052.6(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4031318