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_1555368
_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_absolute_configuration unk
_chemical_formula_moiety         'C H4 O, 0.5(H2 O), C18 H16 N2 O'
_chemical_formula_sum            'C19 H21 N2 O2.5'
_chemical_formula_weight         317.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-30
_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                 90.682(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5014(10)
_cell_length_b                   17.2076(19)
_cell_length_c                   9.9401(10)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.36
_cell_volume                     1625.1(3)
_computing_cell_refinement       'SAINT (8.27b) (Bruker, 2012)'
_computing_data_collection       'Apex2 (2012.2-0) (Bruker, 2012)'
_computing_data_reduction        'SAINT (8.27b) (Bruker, 2012)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26894
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.14
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0300 before and 0.0234 after correction.
The Ratio of minimum to maximum transmission is 0.8961.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       "'irregular"
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         9944
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0668P)^2^+0.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                9658
_reflns_number_total             9944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02680_si_002.cif
_cod_data_source_block           tp2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2022-05-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C H4 O), H2 O, 2(C18 H16 N2 O)'
_cod_original_formula_sum        'C38 H42 N4 O5'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     634.76
_cod_database_code               1555368
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3B), O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3A), C12(H12), C13(H13), N2(H2), C3(H3), C4(H4), C10(H10),
 C11(H11), C5(H5), C6(H6), C22(H22), C21(H21), C28(H28), C29(H29), C30(H30),
 N4(H4A), C31(H31), C24(H24), C23(H23)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C38(H38A,H38B,H38C), C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'