An Unexpected Rearrangement That Disassembles Alkyne Moiety Through Formal Nitrogen Atom Insertion between Two Acetylenic Carbons and Related Cascade Transformations: New Approach toSampangineDerivatives and Polycyclic Aromatic Amides
Sergei F. Vasilevsky; Denis S. Baranov; Victor I. Mamatyuk; Yury V. Gatilov; Igor V. Alabugin; Journal of Organic Chemistry 74 (2009) 6143–6150; doi:10.1021/jo9008904

data_4024756
_publ_section_title
;
An Unexpected Rearrangement That Disassembles Alkyne Moiety Through Formal
Nitrogen Atom Insertion between Two Acetylenic Carbons and Related Cascade
Transformations: New Approach toSampangineDerivatives and Polycyclic
Aromatic Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6143
_journal_page_last               6150
_journal_paper_doi               10.1021/jo9008904
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H13 N O2'
_chemical_formula_sum            'C22 H13 N O2'
_chemical_formula_weight         323.33
_chemical_melting_point          623
_chemical_name_systematic
; 
 1-phenyl-3H-dibenzo[de,h]isoquinolin-3,7(2H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.808(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5227(15)
_cell_length_b                   14.0439(16)
_cell_length_c                   11.1407(14)
_cell_measurement_reflns_used    41
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      11.73
_cell_measurement_theta_min      2.02
_cell_volume                     1579.7(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        '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  'Bruker P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3673
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0.91
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_correction_T_min  0.8974
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0047(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0579P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1878
_reflns_number_total             3111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9008904_si_002.cif
_cod_data_source_block           vasi
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024756