Iodine-catalyzed synthesis of dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide.
Feng, Bin-Bin; Lu, Lian; Li, Chao; Wang, Xiang-Shan; Organic & biomolecular chemistry 14 (2016) 2774–2779; doi:10.1039/c5ob02620b

data_7154956
_publ_section_title
;
 Iodine-catalyzed synthesis of
 dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction
 involving double elimination of hydrogen bromide.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2774
_journal_page_last               2779
_journal_paper_doi               10.1039/c5ob02620b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C27 H23 N3 O3'
_chemical_formula_weight         437.48
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-19 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   14.9522(6)
_cell_length_b                   14.9522(6)
_cell_length_c                   39.844(3)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.72
_cell_volume                     8907.9(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            52539
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3680
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0798P)^2^+4.2141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                3131
_reflns_number_total             3932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02620b2.cif
_cod_data_source_block           3k
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154956.cif.
;
_cod_original_cell_volume        8907.9(9)
_cod_original_sg_symbol_H-M      I4(1)/a
_cod_database_code               7154956