Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies.
Palazzo, Teresa A.; Patra, Digambara; Yang, Joung S.; El Khoury, Elsy; Appleton, Mackenzie G.; Haddadin, Makhluf J.; Tantillo, Dean J.; Kurth, Mark J.; Organic letters 17 (2015) 5732–5735; doi:10.1021/acs.orglett.5b02680

data_1555369
_publ_section_title
;
 Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies
 and Photophysical Studies.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5732
_journal_page_last               5735
_journal_paper_doi               10.1021/acs.orglett.5b02680
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         '3(C2 H6 O), C36 H28 N4 O2'
_chemical_formula_sum            'C42 H46 N4 O5'
_chemical_formula_weight         686.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.2480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.8506(5)
_cell_length_b                   6.80200(10)
_cell_length_c                   25.1773(5)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      71.86
_cell_measurement_theta_min      3.44
_cell_volume                     3438.21(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.15
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            31371
_diffrn_reflns_theta_full        71.89
_diffrn_reflns_theta_max         71.89
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  0.9133
_exptl_absorpt_correction_T_min  0.8049
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         6509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0975P)^2^+3.3278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1775
_reflns_number_gt                5680
_reflns_number_total             6509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02680_si_003.cif
_cod_data_source_block           tp14_1
_cod_database_code               1555369
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,
 H36B), C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C13(H13), C12(H12), C31(H31), C30(H30), C29(H29), C8(H8),
 C7(H7), C6(H6), C5(H5), C28(H28), N4(H4), C24(H24), C23(H23), C22(H22),
 C21(H21), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C40(H40A,H40B,H40C), C38(H38A,H38B,H38C)
;
_olex2_submission_special_instructions 'No special instructions were received'