#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229145.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_2229145
loop_
_publ_author_name
'Wu, Xiang-Yang'
'Xu, Xiang-Jun'
'Wang, Xiang-Cheng'
_publ_section_title
;
 4,5-Dicarboxynaphthalene-1,8-dicarboxylic
 anhydride--1,10-phenanthroline (1/1)
;
_journal_coeditor_code           LX2183
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o474
_journal_paper_doi               10.1107/S1600536811002492
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H8 N2, C14 H6 O7'
_chemical_formula_moiety         'C12 H8 N2, C14 H6 O7'
_chemical_formula_sum            'C26 H14 N2 O7'
_chemical_formula_weight         466.39
_chemical_name_systematic
;
4,5-Dicarboxynaphthalene-1,8-dicarboxylic anhydride--1,10-phenanthroline (1/1)
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.267(6)
_cell_angle_beta                 92.278(5)
_cell_angle_gamma                101.256(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0189(5)
_cell_length_b                   10.1588(7)
_cell_length_c                   11.2140(8)
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9554
_cell_measurement_theta_min      4.0818
_cell_volume                     972.42(12)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and  DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6756
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.09
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.414
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0558
_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)+(0.1188P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                2679
_reflns_number_total             3416
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2183.cif
_cod_data_source_block           I
_cod_original_cell_volume        972.42(11)
_cod_database_code               2229145
_cod_database_fobs_code          2229145
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.55753(16) 0.06531(14) 0.84023(14) 0.0425(4) Uani d . 1 . .
O O2 0.79210(15) 0.19823(17) 0.87789(16) 0.0469(4) Uani d . 1 . .
H H2A 0.8273 0.1546 0.8181 0.070 Uiso calc R 1 . .
O O3 0.57213(15) 0.23703(14) 1.08928(14) 0.0399(4) Uani d . 1 . .
O O4 0.33967(16) 0.10420(17) 1.07563(16) 0.0471(4) Uani d . 1 . .
H H4 0.3822 0.0657 1.1189 0.071 Uiso calc R 1 . .
O O5 0.04091(17) 0.56071(18) 0.81155(17) 0.0538(5) Uani d . 1 . .
O O6 0.23485(16) 0.57884(15) 0.70001(13) 0.0415(4) Uani d . 1 . .
O O7 0.4382(2) 0.6322(2) 0.60562(17) 0.0583(5) Uani d . 1 . .
N N1 -0.00536(18) 0.06070(18) 0.76513(16) 0.0364(4) Uani d . 1 . .
N N2 -0.0387(2) 0.2209(2) 0.60381(17) 0.0437(4) Uani d . 1 . .
C C1 -0.0510(3) 0.2947(3) 0.5239(2) 0.0510(6) Uani d . 1 . .
H H1 -0.1358 0.3342 0.5238 0.061 Uiso calc R 1 . .
C C2 0.0537(3) 0.3179(2) 0.4397(2) 0.0512(6) Uani d . 1 . .
H H2 0.0392 0.3718 0.3859 0.061 Uiso calc R 1 . .
C C3 0.1778(3) 0.2602(3) 0.4375(2) 0.0498(6) Uani d . 1 . .
H H3 0.2494 0.2740 0.3819 0.060 Uiso calc R 1 . .
C C4 0.1968(2) 0.1796(2) 0.5201(2) 0.0421(5) Uani d . 1 . .
C C5 0.3233(3) 0.1145(3) 0.5236(3) 0.0587(7) Uani d . 1 . .
H H5 0.3993 0.1286 0.4717 0.070 Uiso calc R 1 . .
C C6 0.3346(3) 0.0337(3) 0.6003(3) 0.0567(7) Uani d . 1 . .
H H6 0.4176 -0.0082 0.5995 0.068 Uiso calc R 1 . .
C C7 0.2219(2) 0.0106(2) 0.6831(2) 0.0385(5) Uani d . 1 . .
C C8 0.2284(2) -0.0737(2) 0.7640(2) 0.0422(5) Uani d . 1 . .
H H8 0.3086 -0.1189 0.7647 0.051 Uiso calc R 1 . .
C C9 0.1178(2) -0.0901(2) 0.8420(2) 0.0405(5) Uani d . 1 . .
H H9 0.1211 -0.1472 0.8949 0.049 Uiso calc R 1 . .
C C10 0.0006(2) -0.0202(2) 0.84104(19) 0.0395(5) Uani d . 1 . .
H H10 -0.0749 -0.0301 0.8942 0.047 Uiso calc R 1 . .
C C11 0.1000(2) 0.0779(2) 0.68408(18) 0.0325(4) Uani d . 1 . .
C C12 0.0848(2) 0.1632(2) 0.60101(18) 0.0348(4) Uani d . 1 . .
C C13 0.2358(2) 0.44630(19) 0.85406(18) 0.0314(4) Uani d . 1 . .
C C14 0.1623(2) 0.3913(2) 0.9408(2) 0.0375(5) Uani d . 1 . .
H H14 0.0672 0.4080 0.9601 0.045 Uiso calc R 1 . .
C C15 0.2311(2) 0.3098(2) 1.00005(19) 0.0361(4) Uani d . 1 . .
H H15 0.1822 0.2756 1.0611 0.043 Uiso calc R 1 . .
C C16 0.3691(2) 0.27875(19) 0.97076(17) 0.0303(4) Uani d . 1 . .
C C25 0.4381(2) 0.20230(19) 1.05024(17) 0.0316(4) Uani d . 1 . .
C C26 0.6530(2) 0.1802(2) 0.85624(19) 0.0350(4) Uani d . 1 . .
C C17 0.4462(2) 0.32898(18) 0.87661(17) 0.0282(4) Uani d . 1 . .
C C18 0.5859(2) 0.2975(2) 0.83327(18) 0.0330(4) Uani d . 1 . .
C C19 0.6576(2) 0.3638(2) 0.7515(2) 0.0417(5) Uani d . 1 . .
H H19 0.7522 0.3482 0.7293 0.050 Uiso calc R 1 . .
C C20 0.5921(2) 0.4540(2) 0.7011(2) 0.0419(5) Uani d . 1 . .
H H20 0.6428 0.4974 0.6459 0.050 Uiso calc R 1 . .
C C21 0.4528(2) 0.4785(2) 0.73298(18) 0.0338(4) Uani d . 1 . .
C C22 0.3780(2) 0.41784(18) 0.82119(17) 0.0289(4) Uani d . 1 . .
C C23 0.3816(2) 0.5682(2) 0.67520(19) 0.0389(5) Uani d . 1 . .
C C24 0.1622(2) 0.5316(2) 0.79219(19) 0.0371(5) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C26 O2 H2A . . 109.5 ?
C25 O4 H4 . . 109.5 ?
C24 O6 C23 . . 123.76(15) ?
C10 N1 C11 . . 122.47(17) ?
C1 N2 C12 . . 116.5(2) ?
N2 C1 C2 . . 124.6(2) ?
N2 C1 H1 . . 117.7 ?
C2 C1 H1 . . 117.7 ?
C3 C2 C1 . . 118.6(2) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 119.4(2) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C12 C4 C3 . . 117.3(2) ?
C12 C4 C5 . . 119.7(2) ?
C3 C4 C5 . . 123.1(2) ?
C6 C5 C4 . . 121.4(2) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 121.4(2) ?
C5 C6 H6 . . 119.3 ?
C7 C6 H6 . . 119.3 ?
C8 C7 C11 . . 118.72(19) ?
C8 C7 C6 . . 123.41(19) ?
C11 C7 C6 . . 117.86(19) ?
C9 C8 C7 . . 120.47(19) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 118.9(2) ?
C8 C9 H9 . . 120.6 ?
C10 C9 H9 . . 120.6 ?
N1 C10 C9 . . 120.8(2) ?
N1 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
N1 C11 C7 . . 118.59(18) ?
N1 C11 C12 . . 120.00(17) ?
C7 C11 C12 . . 121.40(18) ?
N2 C12 C4 . . 123.60(19) ?
N2 C12 C11 . . 118.22(18) ?
C4 C12 C11 . . 118.17(18) ?
C14 C13 C22 . . 120.67(17) ?
C14 C13 C24 . . 119.01(17) ?
C22 C13 C24 . . 120.29(17) ?
C13 C14 C15 . . 119.51(18) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C16 C15 C14 . . 121.89(18) ?
C16 C15 H15 . . 119.1 ?
C14 C15 H15 . . 119.1 ?
C15 C16 C17 . . 120.23(16) ?
C15 C16 C25 . . 116.49(16) ?
C17 C16 C25 . . 123.04(16) ?
O3 C25 O4 . . 125.51(17) ?
O3 C25 C16 . . 121.47(16) ?
O4 C25 C16 . . 112.93(16) ?
O2 C26 O1 . . 125.89(18) ?
O2 C26 C18 . . 119.39(17) ?
O1 C26 C18 . . 114.43(16) ?
C22 C17 C16 . . 117.17(16) ?
C22 C17 C18 . . 117.40(17) ?
C16 C17 C18 . . 125.43(16) ?
C19 C18 C17 . . 120.01(17) ?
C19 C18 C26 . . 114.89(17) ?
C17 C18 C26 . . 124.54(16) ?
C18 C19 C20 . . 121.70(18) ?
C18 C19 H19 . . 119.2 ?
C20 C19 H19 . . 119.2 ?
C21 C20 C19 . . 119.95(19) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C20 C21 C22 . . 120.37(18) ?
C20 C21 C23 . . 119.60(18) ?
C22 C21 C23 . . 120.03(17) ?
C13 C22 C21 . . 119.40(16) ?
C13 C22 C17 . . 120.38(17) ?
C21 C22 C17 . . 120.23(17) ?
O7 C23 O6 . . 116.28(18) ?
O7 C23 C21 . . 125.9(2) ?
O6 C23 C21 . . 117.81(17) ?
O5 C24 O6 . . 116.34(17) ?
O5 C24 C13 . . 125.90(19) ?
O6 C24 C13 . . 117.71(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C26 . 1.276(2) ?
O2 C26 . 1.237(2) ?
O2 H2A . 0.8200 ?
O3 C25 . 1.222(2) ?
O4 C25 . 1.295(2) ?
O4 H4 . 0.8200 ?
O5 C24 . 1.202(3) ?
O6 C24 . 1.380(3) ?
O6 C23 . 1.382(3) ?
O7 C23 . 1.201(3) ?
N1 C10 . 1.327(3) ?
N1 C11 . 1.357(3) ?
N2 C1 . 1.317(3) ?
N2 C12 . 1.354(3) ?
C1 C2 . 1.391(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.359(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.405(3) ?
C3 H3 . 0.9300 ?
C4 C12 . 1.398(3) ?
C4 C5 . 1.429(3) ?
C5 C6 . 1.341(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.428(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.399(3) ?
C7 C11 . 1.403(3) ?
C8 C9 . 1.365(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.384(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.439(3) ?
C13 C14 . 1.369(3) ?
C13 C22 . 1.412(3) ?
C13 C24 . 1.469(3) ?
C14 C15 . 1.396(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.376(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.430(3) ?
C16 C25 . 1.507(2) ?
C26 C18 . 1.508(3) ?
C17 C22 . 1.429(2) ?
C17 C18 . 1.434(3) ?
C18 C19 . 1.376(3) ?
C19 C20 . 1.396(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.372(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.416(3) ?
C21 C23 . 1.466(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A N1 1_655 0.82 1.97 2.683(2) 144
O4 H4 O1 2_657 0.82 1.69 2.4637(18) 158
C2 H2 O5 2_566 0.93 2.59 3.481(3) 161
C8 H8 O3 2_657 0.93 2.57 3.312(3) 137
C10 H10 O4 2_557 0.93 2.42 3.258(3) 150
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656475
