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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/62/1506208.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506208
loop_
_publ_author_name
'Gryko, Daniel T.'
'Piechowska, Joanna'
'Tasior, Mariusz'
'Waluk, Jacek'
'Orzanowska, Grazyna'
_publ_section_title
;
 From bifunctional nucleophilic behavior of DBU to a new heterocyclic
 fluorescent platform.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4747
_journal_page_last               4750
_journal_paper_doi               10.1021/ol061827m
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C17 H18 N4'
_chemical_formula_weight         278.35
_chemical_name_common            amino-pyrrolo[2,3-b]quinoxaline
_chemical_name_systematic
;
 1H-3a,8,13,13b-tetraazabenzo[b]cyclohepta[1,2,3-jk]fluorene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.83(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4562(12)
_cell_length_b                   16.273(3)
_cell_length_c                   11.316(2)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      0.998
_cell_volume                     1365.9(5)
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3349
_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1130P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1954
_reflns_number_gt                955
_reflns_number_total             1756
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol061827msi20060904_103135.cif
_cod_data_source_block           shelxs97
_cod_original_cell_volume        1365.9
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1506208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N3 N 0.7124(5) 0.1245(2) 0.4365(3) 0.0381(10) Uani 1 1 d .
N2 N 0.7794(5) 0.0353(2) 0.6044(3) 0.0436(10) Uani 1 1 d .
C10 C 0.6676(5) 0.0452(3) 0.2510(4) 0.0367(11) Uani 1 1 d .
C5 C 0.6786(5) 0.1199(2) 0.3137(4) 0.0350(11) Uani 1 1 d .
C11 C 0.7236(5) -0.0260(2) 0.4236(4) 0.0333(11) Uani 1 1 d .
N4 N 0.6870(4) -0.0308(2) 0.3075(3) 0.0396(10) Uani 1 1 d .
C6 C 0.6614(5) 0.1945(3) 0.2487(4) 0.0392(12) Uani 1 1 d .
H6 H 0.6674 0.2453 0.2902 0.047 Uiso 1 1 calc R
C12 C 0.7579(5) -0.0891(3) 0.5051(4) 0.0319(11) Uani 1 1 d .
C8 C 0.6237(6) 0.1198(3) 0.0652(4) 0.0425(12) Uani 1 1 d .
H8 H 0.6050 0.1194 -0.0191 0.051 Uiso 1 1 calc R
C17 C 0.7946(5) -0.0510(3) 0.6161(4) 0.0403(12) Uani 1 1 d .
C4 C 0.7353(5) 0.0517(3) 0.4855(4) 0.0364(12) Uani 1 1 d .
C9 C 0.6384(6) 0.0472(3) 0.1265(4) 0.0424(12) Uani 1 1 d .
H9 H 0.6286 -0.0031 0.0837 0.051 Uiso 1 1 calc R
C3 C 0.7831(6) 0.0958(3) 0.6993(4) 0.0415(12) Uani 1 1 d .
H3A H 0.6598 0.1043 0.7221 0.050 Uiso 1 1 calc R
H3B H 0.8279 0.1490 0.6715 0.050 Uiso 1 1 calc R
C7 C 0.6361(5) 0.1944(3) 0.1262(4) 0.0442(13) Uani 1 1 d .
H7 H 0.6271 0.2448 0.0837 0.053 Uiso 1 1 calc R
N1 N 0.8525(5) -0.0791(3) 0.7287(4) 0.0659(14) Uani 1 1 d .
C14 C 0.7395(6) -0.2369(3) 0.5672(4) 0.0423(12) Uani 1 1 d .
H14A H 0.7512 -0.2934 0.5366 0.051 Uiso 1 1 calc R
H14B H 0.6146 -0.2300 0.5881 0.051 Uiso 1 1 calc R
C13 C 0.7731(6) -0.1763(3) 0.4709(4) 0.0440(13) Uani 1 1 d .
H13A H 0.8955 -0.1859 0.4471 0.053 Uiso 1 1 calc R
H13B H 0.6858 -0.1872 0.4007 0.053 Uiso 1 1 calc R
C1 C 0.8519(7) -0.0199(3) 0.8386(4) 0.0540(14) Uani 1 1 d .
H1A H 0.7300 -0.0187 0.8660 0.065 Uiso 1 1 calc R
H1B H 0.9373 -0.0406 0.9046 0.065 Uiso 1 1 calc R
C15 C 0.8693(7) -0.2259(3) 0.6776(4) 0.0528(14) Uani 1 1 d .
H15A H 0.8741 -0.2783 0.7222 0.063 Uiso 1 1 calc R
H15B H 0.9908 -0.2164 0.6522 0.063 Uiso 1 1 calc R
C16 C 0.8321(7) -0.1594(3) 0.7606(6) 0.0744(18) Uani 1 1 d .
H16A H 0.7063 -0.1663 0.7796 0.089 Uiso 1 1 calc R
H16B H 0.9109 -0.1686 0.8352 0.089 Uiso 1 1 calc R
C2 C 0.9055(6) 0.0658(3) 0.8057(4) 0.0426(12) Uani 1 1 d .
H2A H 1.0322 0.0658 0.7865 0.051 Uiso 1 1 calc R
H2B H 0.8965 0.1033 0.8738 0.051 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 N3 C5 112.1(4)
C4 N2 C17 107.0(4)
C4 N2 C3 125.1(4)
C17 N2 C3 127.4(4)
N4 C10 C9 118.6(4)
N4 C10 C5 122.6(4)
C9 C10 C5 118.8(4)
N3 C5 C10 123.2(4)
N3 C5 C6 118.1(4)
C10 C5 C6 118.7(4)
N4 C11 C12 128.6(4)
N4 C11 C4 122.2(4)
C12 C11 C4 109.1(4)
C11 N4 C10 113.9(4)
C7 C6 C5 121.1(4)
C11 C12 C17 105.9(4)
C11 C12 C13 123.4(4)
C17 C12 C13 130.2(4)
C9 C8 C7 120.2(4)
N1 C17 C12 133.9(4)
N1 C17 N2 115.5(4)
C12 C17 N2 110.4(4)
N3 C4 N2 126.5(4)
N3 C4 C11 125.9(4)
N2 C4 C11 107.5(4)
C8 C9 C10 121.6(4)
N2 C3 C2 109.5(3)
C6 C7 C8 119.5(4)
C16 N1 C17 121.8(5)
C16 N1 C1 111.6(4)
C17 N1 C1 120.0(4)
C13 C14 C15 112.4(4)
C12 C13 C14 114.6(4)
C2 C1 N1 110.5(4)
C16 C15 C14 117.9(4)
N1 C16 C15 119.9(5)
C1 C2 C3 109.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C4 1.312(5)
N3 C5 1.389(5)
N2 C4 1.378(5)
N2 C17 1.415(6)
N2 C3 1.455(5)
C10 N4 1.394(5)
C10 C9 1.405(6)
C10 C5 1.406(6)
C5 C6 1.418(6)
C11 N4 1.316(5)
C11 C12 1.388(6)
C11 C4 1.444(6)
C6 C7 1.381(6)
C12 C17 1.403(6)
C12 C13 1.478(6)
C8 C9 1.369(6)
C8 C7 1.394(6)
C17 N1 1.381(6)
C3 C2 1.515(6)
N1 C16 1.368(6)
N1 C1 1.574(6)
C14 C13 1.508(6)
C14 C15 1.511(6)
C1 C2 1.508(6)
C15 C16 1.477(7)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21151928 ChemSpider
2 101419367 PubChem
