#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/95/2219592.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2219592
loop_
_publ_author_name
'Liu, Chun-Bo'
'Wang, Jian'
'Li, Xiu-Ying'
'Che, Guang-Bo'
'Liu, Yang'
_publ_section_title
;10,11,12,13-Tetrahydro-4,5,9,14-tetraazadibenz[a,c]anthracene--benzene-1,4-dicarboxylic
 acid (2/1)
;
_journal_coeditor_code           HB2788
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1877
_journal_paper_doi               10.1107/S1600536808027785
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '2C18 H14 N4 , C8 H6 O4'
_chemical_formula_moiety         '2C18 H14 N4 , C8 H6 O4'
_chemical_formula_sum            'C44 H34 N8 O4'
_chemical_formula_weight         738.80
_chemical_name_systematic
;
10,11,12,13-Tetrahydro-4,5,9,14-tetraazadibenz[a,c]anthracene--
benzene-1,4-dicarboxylic acid (2/1)
;
_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           SHELXL97
_cell_angle_alpha                101.469(9)
_cell_angle_beta                 97.429(9)
_cell_angle_gamma                109.697(6)
_cell_formula_units_Z            1
_cell_length_a                   7.266(4)
_cell_length_b                   9.917(5)
_cell_length_c                   13.564(9)
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.26
_cell_volume                     881.2(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7636
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1800
_reflns_number_gt                1394
_reflns_number_total             3444
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2788.cif
_cod_data_source_block           I
_cod_database_code               2219592
_cod_database_fobs_code          2219592
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.7589(5) 0.5815(4) 1.2595(3) 0.0603(10) Uani d . 1
H H1 0.7594 0.6000 1.3295 0.072 Uiso calc R 1
C C2 0.7631(5) 0.6947(4) 1.2121(3) 0.0593(9) Uani d . 1
H H2 0.7692 0.7861 1.2495 0.071 Uiso calc R 1
C C3 0.7581(4) 0.6668(4) 1.1082(3) 0.0534(9) Uani d . 1
H H3 0.7589 0.7394 1.0739 0.064 Uiso calc R 1
C C4 0.7517(4) 0.5297(3) 1.0542(2) 0.0411(8) Uani d . 1
C C5 0.7492(4) 0.4942(3) 0.9448(2) 0.0418(8) Uani d . 1
C C6 0.7476(4) 0.5624(4) 0.7934(3) 0.0473(8) Uani d . 1
C C7 0.7508(5) 0.6785(4) 0.7365(2) 0.0607(10) Uani d . 1
H H7A 0.8810 0.7585 0.7590 0.073 Uiso calc R 1
H H7B 0.6518 0.7193 0.7543 0.073 Uiso calc R 1
C C8 0.7086(6) 0.6201(4) 0.6202(3) 0.0773(12) Uani d . 1
H H8A 0.5654 0.5694 0.5943 0.093 Uiso calc R 1
H H8B 0.7534 0.7030 0.5898 0.093 Uiso calc R 1
C C9 0.8103(6) 0.5164(4) 0.5882(3) 0.0779(12) Uani d . 1
H H9A 0.9537 0.5678 0.6125 0.093 Uiso calc R 1
H H9B 0.7826 0.4845 0.5137 0.093 Uiso calc R 1
C C10 0.7414(6) 0.3822(4) 0.6306(2) 0.0669(10) Uani d . 1
H H10A 0.6063 0.3186 0.5940 0.080 Uiso calc R 1
H H10B 0.8271 0.3265 0.6187 0.080 Uiso calc R 1
C C11 0.7453(4) 0.4230(4) 0.7430(2) 0.0485(8) Uani d . 1
C C12 0.7473(4) 0.3561(3) 0.8947(2) 0.0433(8) Uani d . 1
C C13 0.7493(4) 0.2468(3) 0.9524(2) 0.0439(8) Uani d . 1
C C14 0.7547(4) 0.1100(4) 0.9065(3) 0.0535(9) Uani d . 1
H H14 0.7545 0.0847 0.8367 0.064 Uiso calc R 1
C C15 0.7602(5) 0.0130(4) 0.9645(3) 0.0578(9) Uani d . 1
H H15 0.7664 -0.0782 0.9355 0.069 Uiso calc R 1
C C16 0.7563(5) 0.0539(4) 1.0681(3) 0.0622(10) Uani d . 1
H H16 0.7582 -0.0131 1.1071 0.075 Uiso calc R 1
C C17 0.7489(4) 0.2799(3) 1.0574(2) 0.0431(8) Uani d . 1
C C18 0.7504(4) 0.4245(3) 1.1102(2) 0.0429(8) Uani d . 1
C C19 0.7010(6) 0.0878(4) 1.3406(3) 0.0611(10) Uani d . 1
C C20 0.5949(5) 0.0433(3) 1.4226(2) 0.0527(9) Uani d . 1
C C21 0.4077(6) 0.0460(4) 1.4252(3) 0.0597(10) Uani d . 1
H H21 0.3439 0.0761 1.3747 0.072 Uiso calc R 1
C C22 0.6860(5) -0.0042(4) 1.4971(3) 0.0611(10) Uani d . 1
H H22 0.8116 -0.0082 1.4950 0.073 Uiso calc R 1
N N1 0.7543(4) 0.4499(3) 1.2122(2) 0.0533(7) Uani d . 1
N N2 0.7502(4) 0.1824(3) 1.1147(2) 0.0513(7) Uani d . 1
N N3 0.7496(4) 0.5981(3) 0.89318(19) 0.0472(7) Uani d . 1
N N4 0.7442(4) 0.3203(3) 0.79299(19) 0.0491(7) Uani d . 1
O O1 0.8422(4) 0.0570(3) 1.3217(2) 0.0853(9) Uani d . 1
O O2 0.6271(4) 0.1674(3) 1.29255(18) 0.0766(8) Uani d . 1
H H2A 0.6112 0.1355 1.2302 0.115 Uiso calc R 1
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 124.8(3)
N1 C1 H1 . . 117.6
C2 C1 H1 . . 117.6
C3 C2 C1 . . 117.8(3)
C3 C2 H2 . . 121.1
C1 C2 H2 . . 121.1
C2 C3 C4 . . 119.9(3)
C2 C3 H3 . . 120.1
C4 C3 H3 . . 120.1
C3 C4 C18 . . 117.4(3)
C3 C4 C5 . . 122.5(3)
C18 C4 C5 . . 120.1(3)
N3 C5 C12 . . 121.2(3)
N3 C5 C4 . . 118.5(3)
C12 C5 C4 . . 120.3(3)
N3 C6 C11 . . 121.7(3)
N3 C6 C7 . . 116.9(3)
C11 C6 C7 . . 121.4(3)
C6 C7 C8 . . 113.5(3)
C6 C7 H7A . . 108.9
C8 C7 H7A . . 108.9
C6 C7 H7B . . 108.9
C8 C7 H7B . . 108.9
H7A C7 H7B . . 107.7
C9 C8 C7 . . 112.1(3)
C9 C8 H8A . . 109.2
C7 C8 H8A . . 109.2
C9 C8 H8B . . 109.2
C7 C8 H8B . . 109.2
H8A C8 H8B . . 107.9
C8 C9 C10 . . 111.6(3)
C8 C9 H9A . . 109.3
C10 C9 H9A . . 109.3
C8 C9 H9B . . 109.3
C10 C9 H9B . . 109.3
H9A C9 H9B . . 108.0
C11 C10 C9 . . 112.4(3)
C11 C10 H10A . . 109.1
C9 C10 H10A . . 109.1
C11 C10 H10B . . 109.1
C9 C10 H10B . . 109.1
H10A C10 H10B . . 107.9
N4 C11 C6 . . 121.7(3)
N4 C11 C10 . . 116.5(3)
C6 C11 C10 . . 121.8(3)
N4 C12 C5 . . 121.5(3)
N4 C12 C13 . . 118.5(3)
C5 C12 C13 . . 120.1(3)
C14 C13 C17 . . 118.3(3)
C14 C13 C12 . . 122.0(3)
C17 C13 C12 . . 119.7(3)
C15 C14 C13 . . 119.6(3)
C15 C14 H14 . . 120.2
C13 C14 H14 . . 120.2
C14 C15 C16 . . 118.3(3)
C14 C15 H15 . . 120.8
C16 C15 H15 . . 120.8
N2 C16 C15 . . 124.0(3)
N2 C16 H16 . . 118.0
C15 C16 H16 . . 118.0
N2 C17 C13 . . 122.2(3)
N2 C17 C18 . . 117.4(3)
C13 C17 C18 . . 120.4(3)
N1 C18 C4 . . 123.4(3)
N1 C18 C17 . . 117.1(3)
C4 C18 C17 . . 119.4(3)
O1 C19 O2 . . 123.7(4)
O1 C19 C20 . . 123.6(4)
O2 C19 C20 . . 112.6(4)
C21 C20 C22 . . 119.2(3)
C21 C20 C19 . . 121.8(3)
C22 C20 C19 . . 119.0(4)
C20 C21 C22 . 2_658 120.1(3)
C20 C21 H21 . . 119.9
C22 C21 H21 2_658 . 119.9
C20 C22 C21 . 2_658 120.6(3)
C20 C22 H22 . . 119.7
C21 C22 H22 2_658 . 119.7
C1 N1 C18 . . 116.7(3)
C16 N2 C17 . . 117.6(3)
C6 N3 C5 . . 117.0(3)
C11 N4 C12 . . 116.9(3)
C19 O2 H2A . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.323(4)
C1 C2 . 1.393(4)
C1 H1 . 0.9300
C2 C3 . 1.375(4)
C2 H2 . 0.9300
C3 C4 . 1.393(4)
C3 H3 . 0.9300
C4 C18 . 1.405(4)
C4 C5 . 1.452(4)
C5 N3 . 1.355(3)
C5 C12 . 1.398(4)
C6 N3 . 1.327(4)
C6 C11 . 1.408(4)
C6 C7 . 1.504(4)
C7 C8 . 1.520(4)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.486(5)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.511(4)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.491(4)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 N4 . 1.329(4)
C12 N4 . 1.349(4)
C12 C13 . 1.461(4)
C13 C14 . 1.392(4)
C13 C17 . 1.397(4)
C14 C15 . 1.366(4)
C14 H14 . 0.9300
C15 C16 . 1.389(4)
C15 H15 . 0.9300
C16 N2 . 1.322(4)
C16 H16 . 0.9300
C17 N2 . 1.357(4)
C17 C18 . 1.466(4)
C18 N1 . 1.351(4)
C19 O1 . 1.208(4)
C19 O2 . 1.317(4)
C19 C20 . 1.488(5)
C20 C21 . 1.375(4)
C20 C22 . 1.381(4)
C21 C22 2_658 1.384(4)
C21 H21 . 0.9300
C22 C21 2_658 1.384(4)
C22 H22 . 0.9300
O2 H2A . 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A N2 0.82 2.02 2.694(4) 139
