Synthesis of 2-pyridone-fused 2,2'-bipyridine derivatives. An unexpectedly complex solid state structure of 3,6-dimethyl-9H-4,5,9-triazaphenanthren-10-one.
Jónsson, Stefán; Arribas, Carlos Solano; Wendt, Ola F.; Siegel, Jay S.; Wärnmark, Kenneth; Organic & biomolecular chemistry 3 (2005) 996–1001; doi:10.1039/b417485b

data_7150119
_publ_section_title
;
 Synthesis of 2-pyridone-fused 2,2'-bipyridine derivatives. An
 unexpectedly complex solid state structure of
 3,6-dimethyl-9H-4,5,9-triazaphenanthren-10-one.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              996
_journal_page_last               1001
_journal_paper_doi               10.1039/b417485b
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C13 H9.43 N3 O'
_chemical_formula_weight         223.66
_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                72.17(3)
_cell_angle_beta                 80.39(3)
_cell_angle_gamma                86.90(3)
_cell_formula_units_Z            7
_cell_length_a                   10.057(2)
_cell_length_b                   13.722(3)
_cell_length_c                   15.423(3)
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.378
_cell_measurement_theta_min      2.298
_cell_volume                     1997.7(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond (Brandenburg)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21513
_diffrn_reflns_theta_full        31.17
_diffrn_reflns_theta_max         31.17
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             815
_exptl_crystal_size_max          1.02
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         11415
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.2038
_refine_ls_R_factor_gt           0.0977
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2830
_refine_ls_wR_factor_ref         0.3289
_reflns_number_gt                4583
_reflns_number_total             11415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b417485b.txt
_cod_data_source_block           sad2
_cod_original_cell_volume        1997.7(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150119