#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223860.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_2223860
loop_
_publ_author_name
'Deng, Ji-Hua'
'Guo, Meng-Ping'
'Zhang, Qiao-Chu'
'Yuan, Lin'
'Guo, Hui-Rui'
'Mei, Guang-Quan'
_publ_section_title
;
 Naphthalene-1,4,5,8-tetracarboxylic acid
 1,8-anhydride--4,4'-bipyridine (1/1)
;
_journal_coeditor_code           IM2151
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2912
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H6 O7, C10 H8 N2'
_chemical_formula_moiety         'C14 H6 O7, C10 H8 N2'
_chemical_formula_sum            'C24 H14 N2 O7'
_chemical_formula_weight         442.37
_chemical_name_systematic
;
Naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride--4,4'-bipyridine (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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.384(5)
_cell_angle_beta                 85.615(6)
_cell_angle_gamma                83.947(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6193(8)
_cell_length_b                   9.6964(3)
_cell_length_c                   10.1920(10)
_cell_measurement_reflns_used    5003
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.85
_cell_volume                     932.89(12)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6648
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998\\bbr00)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0329
_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/[\s^2^(Fo^2^)+(0.0664P)^2^+0.1626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                2772
_reflns_number_total             3240
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    im2151.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        932.90(10)
_cod_database_code               2223860
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
O O6 1.12369(10) 0.85984(10) 0.57565(9) 0.0273(2) Uani d . 1
O O3 0.55296(10) 0.61928(11) 0.24288(10) 0.0327(3) Uani d . 1
O O7 0.92667(10) 0.94482(10) 0.67238(10) 0.0299(3) Uani d . 1
O O1 0.83856(10) 0.51984(10) 0.08988(9) 0.0296(2) Uani d . 1
O O5 1.31804(10) 0.81386(10) 0.45444(10) 0.0304(3) Uani d . 1
C C8 0.90124(14) 0.79831(13) 0.50961(13) 0.0228(3) Uani d . 1
C C14 0.97444(13) 0.70939(13) 0.42367(13) 0.0207(3) Uani d . 1
C C13 0.89868(13) 0.63253(13) 0.34836(12) 0.0207(3) Uani d . 1
C C11 0.74906(14) 0.65192(13) 0.36207(13) 0.0226(3) Uani d . 1
C C2 0.98025(14) 0.54118(13) 0.26762(13) 0.0219(3) Uani d . 1
C C5 1.12245(14) 0.69889(13) 0.41277(13) 0.0230(3) Uani d . 1
C C10 0.68213(14) 0.74534(14) 0.44146(14) 0.0262(3) Uani d . 1
H H10 0.5828 0.7608 0.4452 0.031 Uiso calc R 1
C C7 0.97886(14) 0.87102(13) 0.59342(13) 0.0243(3) Uani d . 1
C C6 1.19789(14) 0.79167(14) 0.47810(13) 0.0246(3) Uani d . 1
C C12 0.65343(14) 0.56573(14) 0.30445(13) 0.0241(3) Uani d . 1
C C4 1.19675(14) 0.60634(14) 0.33777(14) 0.0261(3) Uani d . 1
H H4 1.2962 0.5972 0.3331 0.031 Uiso calc R 1
C C1 0.91902(14) 0.46243(14) 0.17226(13) 0.0229(3) Uani d . 1
C C9 0.75773(15) 0.81770(14) 0.51654(14) 0.0265(3) Uani d . 1
H H9 0.7098 0.8800 0.5721 0.032 Uiso calc R 1
C C3 1.12416(14) 0.52589(14) 0.26854(14) 0.0257(3) Uani d . 1
H H3 1.1757 0.4585 0.2205 0.031 Uiso calc R 1
N N1 0.46466(12) 0.72761(13) 0.75937(12) 0.0280(3) Uani d . 1
N N2 0.84743(12) 1.16076(13) 1.06975(12) 0.0298(3) Uani d . 1
C C17 0.62220(13) 0.89707(14) 0.87676(13) 0.0228(3) Uani d . 1
C C18 0.70313(13) 0.98835(14) 0.94187(13) 0.0227(3) Uani d . 1
C C23 0.52433(15) 0.95430(15) 0.78427(14) 0.0272(3) Uani d . 1
H H23 0.5101 1.0529 0.7596 0.033 Uiso calc R 1
C C22 0.68533(16) 1.13357(15) 0.91138(14) 0.0305(3) Uani d . 1
H H22 0.6234 1.1769 0.8457 0.037 Uiso calc R 1
C C15 0.55791(15) 0.67228(15) 0.84780(15) 0.0310(3) Uani d . 1
H H15 0.5694 0.5733 0.8706 0.037 Uiso calc R 1
C C24 0.44849(15) 0.86730(15) 0.72895(14) 0.0297(3) Uani d . 1
H H24 0.3820 0.9081 0.6667 0.036 Uiso calc R 1
C C16 0.63843(15) 0.75167(15) 0.90771(15) 0.0302(3) Uani d . 1
H H16 0.7043 0.7076 0.9694 0.036 Uiso calc R 1
C C21 0.75874(16) 1.21431(15) 0.97767(14) 0.0310(3) Uani d . 1
H H21 0.7449 1.3133 0.9561 0.037 Uiso calc R 1
C C20 0.86494(16) 1.02078(16) 1.10009(16) 0.0362(4) Uani d . 1
H H20 0.9275 0.9808 1.1663 0.043 Uiso calc R 1
C C19 0.79578(16) 0.93242(16) 1.03902(15) 0.0331(3) Uani d . 1
H H19 0.8113 0.8338 1.0632 0.040 Uiso calc R 1
O O4 0.68631(10) 0.43151(10) 0.33780(10) 0.0283(2) Uani d . 1
H H4A 0.6303 0.3865 0.3059 0.042 Uiso calc R 1
O O2 0.96983(10) 0.33081(10) 0.18631(10) 0.0280(2) Uani d . 1
H H2 0.9261 0.2867 0.1405 0.042 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O6 0.0303(5) 0.0273(5) 0.0267(5) -0.0074(4) -0.0067(4) -0.0057(4)
O3 0.0249(5) 0.0356(6) 0.0398(6) 0.0001(4) -0.0124(4) -0.0093(5)
O7 0.0389(6) 0.0248(5) 0.0279(5) 0.0009(4) -0.0085(4) -0.0093(4)
O1 0.0328(6) 0.0302(5) 0.0268(5) -0.0008(4) -0.0087(4) -0.0050(4)
O5 0.0256(5) 0.0315(5) 0.0358(6) -0.0100(4) -0.0071(4) -0.0028(4)
C8 0.0273(7) 0.0182(6) 0.0232(7) -0.0038(5) -0.0032(5) -0.0020(5)
C14 0.0237(7) 0.0173(6) 0.0213(6) -0.0036(5) -0.0038(5) -0.0005(5)
C13 0.0232(7) 0.0184(6) 0.0206(6) -0.0039(5) -0.0043(5) -0.0003(5)
C11 0.0235(7) 0.0208(6) 0.0234(7) -0.0028(5) -0.0041(5) -0.0012(5)
C2 0.0247(7) 0.0195(6) 0.0217(6) -0.0043(5) -0.0027(5) -0.0010(5)
C5 0.0247(7) 0.0208(6) 0.0236(7) -0.0050(5) -0.0050(5) 0.0002(5)
C10 0.0207(7) 0.0262(7) 0.0320(8) -0.0013(5) -0.0025(6) -0.0056(6)
C7 0.0289(7) 0.0194(6) 0.0246(7) -0.0027(5) -0.0064(6) -0.0007(5)
C6 0.0274(8) 0.0217(6) 0.0243(7) -0.0038(5) -0.0068(6) 0.0013(5)
C12 0.0203(7) 0.0285(7) 0.0244(7) -0.0039(5) -0.0010(5) -0.0054(6)
C4 0.0191(7) 0.0277(7) 0.0318(7) -0.0039(5) -0.0024(6) -0.0036(6)
C1 0.0230(7) 0.0239(7) 0.0224(7) -0.0045(5) 0.0001(5) -0.0042(5)
C9 0.0279(7) 0.0239(7) 0.0282(7) 0.0002(5) -0.0007(6) -0.0076(6)
C3 0.0239(7) 0.0252(7) 0.0286(7) -0.0013(5) -0.0001(6) -0.0071(6)
N1 0.0241(6) 0.0320(7) 0.0308(6) -0.0072(5) -0.0007(5) -0.0112(5)
N2 0.0283(6) 0.0332(7) 0.0314(7) -0.0050(5) -0.0024(5) -0.0141(5)
C17 0.0203(7) 0.0275(7) 0.0218(7) -0.0029(5) 0.0012(5) -0.0082(5)
C18 0.0205(7) 0.0274(7) 0.0217(7) -0.0027(5) 0.0008(5) -0.0086(5)
C23 0.0296(7) 0.0257(7) 0.0273(7) -0.0055(6) -0.0055(6) -0.0032(6)
C22 0.0365(8) 0.0295(7) 0.0270(7) -0.0056(6) -0.0094(6) -0.0033(6)
C15 0.0279(7) 0.0253(7) 0.0416(8) -0.0015(6) -0.0049(6) -0.0105(6)
C24 0.0279(7) 0.0350(8) 0.0280(7) -0.0072(6) -0.0060(6) -0.0052(6)
C16 0.0267(7) 0.0278(7) 0.0374(8) -0.0002(6) -0.0101(6) -0.0067(6)
C21 0.0391(8) 0.0258(7) 0.0296(8) -0.0083(6) -0.0029(6) -0.0056(6)
C20 0.0358(8) 0.0341(8) 0.0423(9) 0.0034(6) -0.0161(7) -0.0144(7)
C19 0.0363(8) 0.0268(7) 0.0388(8) 0.0013(6) -0.0136(7) -0.0103(6)
O4 0.0290(5) 0.0247(5) 0.0337(6) -0.0094(4) -0.0100(4) -0.0037(4)
O2 0.0312(5) 0.0230(5) 0.0329(6) -0.0025(4) -0.0097(4) -0.0100(4)
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
C7 O6 C6 123.44(11)
C9 C8 C14 120.75(12)
C9 C8 C7 119.01(12)
C14 C8 C7 120.24(12)
C5 C14 C8 119.17(12)
C5 C14 C13 120.74(12)
C8 C14 C13 120.09(12)
C11 C13 C14 117.33(12)
C11 C13 C2 125.99(12)
C14 C13 C2 116.68(12)
C10 C11 C13 120.61(12)
C10 C11 C12 114.95(12)
C13 C11 C12 124.19(11)
C3 C2 C13 120.43(12)
C3 C2 C1 115.54(12)
C13 C2 C1 123.96(12)
C4 C5 C14 120.61(12)
C4 C5 C6 119.51(12)
C14 C5 C6 119.84(12)
C11 C10 C9 121.30(13)
C11 C10 H10 119.3
C9 C10 H10 119.3
O7 C7 O6 116.81(12)
O7 C7 C8 125.34(13)
O6 C7 C8 117.76(12)
O5 C6 O6 116.80(12)
O5 C6 C5 125.81(13)
O6 C6 C5 117.39(12)
O3 C12 O4 126.01(12)
O3 C12 C11 122.11(12)
O4 C12 C11 111.69(11)
C5 C4 C3 119.14(12)
C5 C4 H4 120.4
C3 C4 H4 120.4
O1 C1 O2 126.31(12)
O1 C1 C2 122.40(12)
O2 C1 C2 111.18(11)
C8 C9 C10 119.78(12)
C8 C9 H9 120.1
C10 C9 H9 120.1
C2 C3 C4 122.08(12)
C2 C3 H3 119.0
C4 C3 H3 119.0
C15 N1 C24 117.78(12)
C21 N2 C20 117.59(12)
C16 C17 C23 117.10(12)
C16 C17 C18 121.60(12)
C23 C17 C18 121.28(12)
C22 C18 C19 117.07(12)
C22 C18 C17 121.26(12)
C19 C18 C17 121.63(12)
C24 C23 C17 119.81(13)
C24 C23 H23 120.1
C17 C23 H23 120.1
C21 C22 C18 119.32(13)
C21 C22 H22 120.3
C18 C22 H22 120.3
N1 C15 C16 123.30(13)
N1 C15 H15 118.4
C16 C15 H15 118.4
N1 C24 C23 122.70(13)
N1 C24 H24 118.7
C23 C24 H24 118.7
C15 C16 C17 119.31(13)
C15 C16 H16 120.3
C17 C16 H16 120.3
N2 C21 C22 123.50(13)
N2 C21 H21 118.2
C22 C21 H21 118.2
N2 C20 C19 122.72(14)
N2 C20 H20 118.6
C19 C20 H20 118.6
C20 C19 C18 119.80(14)
C20 C19 H19 120.1
C18 C19 H19 120.1
C12 O4 H4A 109.5
C1 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O6 C7 1.3859(17)
O6 C6 1.3870(17)
O3 C12 1.2193(16)
O7 C7 1.2028(16)
O1 C1 1.2175(16)
O5 C6 1.1977(16)
C8 C9 1.3713(19)
C8 C14 1.4179(19)
C8 C7 1.4742(18)
C14 C5 1.4136(19)
C14 C13 1.4308(18)
C13 C11 1.4305(18)
C13 C2 1.4319(19)
C11 C10 1.3808(19)
C11 C12 1.5105(18)
C2 C3 1.3771(19)
C2 C1 1.5098(18)
C5 C4 1.374(2)
C5 C6 1.4732(18)
C10 C9 1.4001(19)
C10 H10 0.9500
C12 O4 1.3064(16)
C4 C3 1.3961(19)
C4 H4 0.9500
C1 O2 1.3086(16)
C9 H9 0.9500
C3 H3 0.9500
N1 C15 1.3349(19)
N1 C24 1.3387(19)
N2 C21 1.3271(19)
N2 C20 1.342(2)
C17 C16 1.3926(19)
C17 C23 1.3970(19)
C17 C18 1.4933(18)
C18 C22 1.391(2)
C18 C19 1.393(2)
C23 C24 1.3772(19)
C23 H23 0.9500
C22 C21 1.384(2)
C22 H22 0.9500
C15 C16 1.380(2)
C15 H15 0.9500
C24 H24 0.9500
C16 H16 0.9500
C21 H21 0.9500
C20 C19 1.381(2)
C20 H20 0.9500
C19 H19 0.9500
O4 H4A 0.8400
O2 H2 0.8400
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 H2 N2 1_544 0.84 1.77 2.594(2) 167
O4 H4A N1 2_666 0.84 1.74 2.573(2) 171
C16 H16 O1 1_556 0.95 2.36 3.254(2) 157
C22 H22 O3 2_676 0.95 2.57 3.425(2) 150