##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
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data_global
_journal_date_recd_electronic     2009-01-13
_journal_date_accepted     2009-03-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      4
_journal_page_first     m411
_journal_page_last     m411
_journal_paper_category     QM
_journal_coeditor_code     BI2347
_publ_contact_author_name     'Professor Yuan-Fang Ma'
_publ_contact_author_address
;
The Institute of Immunology,
Key Laboratory of Natural Drugs and Immunological
Engineering of Henan Province,
College of Medicine,
Henan University,
Kaifeng 475003,
People's Republic of China
;
_publ_contact_author_email     mayf_hd@126.com
_publ_contact_author_fax     '086 378-3885036'
_publ_contact_author_phone     '086 378-3885036'
_publ_section_title
;\
catena-Poly[[[diaquathulium(III)]-μ-6-carboxynicotinato-μ-pyridine-2,\
5-dicarboxylato] dihydrate]
;
loop_
    _publ_author_name
    _publ_author_address
    'Sheng Li'
;
The Institute of Immunology,
Key Laboratory of Natural Drugs and Immunological Engineering of Henan Province,
College of Medicine,
Henan University,
Kaifeng 475003,
People's Republic of China
;
    'Yue Chen'
;
College of Medicine,
Henan University,
Kaifeng 475003,
People's Republic of China
;
    'Hong-Mei He'
;
College of Medicine,
Henan University,
Kaifeng 475003,
People's Republic of China
;
    'Yuan-Fang Ma'
;
The Institute of Immunology,
Key Laboratory of Natural Drugs and Immunological Engineering of Henan Province,
College of Medicine,
Henan University,
Kaifeng 475003,
People's Republic of China
;
data_I
_publ_section_title
;
catena-Poly[[[diaquathulium(III)]-μ-6-carboxynicotinato-μ-
pyridine-2,5-dicarboxylato] dihydrate]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 N2 O10 Tm, 2(H2 O)'
_chemical_formula_sum     'C14 H15 N2 O12 Tm'
_chemical_formula_iupac     '[Tm (C7 H3 N O4) (C7 H4 N O4) (H2 O)2], 2H2 O'
_chemical_formula_weight     572.21
_chemical_melting_point     ?
_symmetry_cell_setting     tetragonal
_symmetry_space_group_name_H-M     'I -4'
_symmetry_space_group_name_Hall     'I -4'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'y, -x, -z'
    '-y, x, -z'
    'x+1/2, y+1/2, z+1/2'
    '-x+1/2, -y+1/2, z+1/2'
    'y+1/2, -x+1/2, -z+1/2'
    '-y+1/2, x+1/2, -z+1/2'
_cell_length_a     15.1286(12)
_cell_length_b     15.1286(12)
_cell_length_c     14.849(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3398.6(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3085
_cell_measurement_theta_min     1.90
_cell_measurement_theta_max     25.50
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.12
_exptl_crystal_size_mid     0.11
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     2.237
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2224
_exptl_absorpt_coefficient_mu     5.296
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.5688
_exptl_absorpt_correction_T_max     0.6470
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     7093
_diffrn_reflns_av_R_equivalents     0.0314
_diffrn_reflns_av_sigmaI/netI     0.0347
_diffrn_reflns_theta_min     1.90
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3085
_reflns_number_gt     2977
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0447
_refine_ls_R_factor_gt     0.0427
_refine_ls_wR_factor_gt     0.1085
_refine_ls_wR_factor_ref     0.1109
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     3085
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0703P)²+51.4546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     6.957
_refine_diff_density_min     -1.184
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1444 Friedel pairs'
_refine_ls_abs_structure_Flack     0.49(2)
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'
    'Tm' 'Tm' -0.3139 5.2483
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    Tm Tm1 0.30232(3) 0.22523(3) 0.22714(3) 0.01768(14) Uani d . 1 . .
    C C1 0.1831(5) 0.4107(6) 0.1942(6) 0.0111(18) Uani d . 1 . .
    C C2 0.1327(6) 0.4765(6) 0.1551(6) 0.0164(19) Uani d . 1 . .
    H H2A 0.1115 0.5229 0.1900 0.020 Uiso calc R 1 . .
    C C3 0.1140(6) 0.4732(6) 0.0642(6) 0.0156(18) Uani d . 1 . .
    H H3A 0.0816 0.5185 0.0376 0.019 Uiso calc R 1 . .
    C C4 0.1428(6) 0.4034(6) 0.0126(6) 0.0132(17) Uani d . 1 . .
    C C5 0.1880(6) 0.3365(6) 0.0577(7) 0.0170(19) Uani d . 1 . .
    H H5A 0.2041 0.2864 0.0253 0.020 Uiso calc R 1 . .
    C C6 0.2156(6) 0.4129(6) 0.2916(5) 0.0115(19) Uani d . 1 . .
    C C7 0.1298(6) 0.3968(6) -0.0877(7) 0.017(2) Uani d . 1 . .
    C C8 0.1188(6) 0.1237(6) 0.1724(6) 0.0133(18) Uani d . 1 . .
    C C9 0.0969(5) 0.1481(5) 0.2698(7) 0.0091(15) Uani d . 1 . .
    C C10 0.0232(6) 0.1189(6) 0.3171(7) 0.0160(18) Uani d . 1 . .
    H H10A -0.0196 0.0856 0.2876 0.019 Uiso calc R 1 . .
    C C11 0.0128(6) 0.1380(6) 0.4051(7) 0.0160(19) Uani d . 1 . .
    H H11A -0.0358 0.1162 0.4364 0.019 Uiso calc R 1 . .
    C C12 0.0768(6) 0.1922(6) 0.4506(6) 0.0103(16) Uani d . 1 . .
    C C13 0.1453(6) 0.2202(6) 0.3982(6) 0.0136(18) Uani d . 1 . .
    H H13A 0.1868 0.2571 0.4251 0.016 Uiso calc R 1 . .
    C C14 0.0689(6) 0.2110(7) 0.5496(6) 0.016(2) Uani d . 1 . .
    N N1 0.1582(5) 0.1994(5) 0.3117(6) 0.0152(16) Uani d . 1 . .
    N N2 0.2099(5) 0.3404(5) 0.1464(5) 0.0117(15) Uani d . 1 . .
    O O1 0.2739(4) 0.3555(4) 0.3098(5) 0.0170(14) Uani d . 1 . .
    H H1 0.3059 0.3647 0.3559 0.025 Uiso d R 1 . .
    O O2 0.1850(6) 0.4687(6) 0.3432(5) 0.0315(18) Uani d . 1 . .
    O O3 0.1614(5) 0.3285(4) -0.1275(5) 0.0191(14) Uani d . 1 . .
    O O4 0.0916(5) 0.4563(5) -0.1268(5) 0.0221(15) Uani d . 1 . .
    O O5 0.1938(4) 0.1458(4) 0.1461(5) 0.0177(14) Uani d . 1 . .
    O O6 0.0627(5) 0.0860(5) 0.1274(5) 0.0221(15) Uani d . 1 . .
    O O7 0.0051(5) 0.1854(6) 0.5920(5) 0.0281(17) Uani d . 1 . .
    O O8 0.1335(4) 0.2552(5) 0.5835(5) 0.0215(15) Uani d . 1 . .
    O O9 0.3709(5) 0.0809(4) 0.2010(4) 0.0189(14) Uani d . 1 . .
    H H91 0.3827 0.0691 0.2556 0.028 Uiso d R 1 . .
    H H92 0.4227 0.0840 0.1790 0.028 Uiso d R 1 . .
    O O10 0.4516(4) 0.2745(5) 0.2619(5) 0.0217(15) Uani d . 1 . .
    H H101 0.4653 0.2877 0.2080 0.033 Uiso d R 1 . .
    H H102 0.4887 0.2336 0.2727 0.033 Uiso d R 1 . .
    O O11 0.2679(7) 0.0199(6) 0.0226(6) 0.042(2) Uani d . 1 . .
    H H111 0.2463 0.0571 0.0594 0.063 Uiso d R 1 . .
    H H112 0.2823 0.0234 -0.0326 0.063 Uiso d R 1 . .
    O O12 0.1257(6) -0.0911(6) 0.0638(6) 0.041(2) Uani d . 1 . .
    H H121 0.0724 -0.0900 0.0821 0.061 Uiso d R 1 . .
    H H122 0.1146 -0.0831 0.0083 0.061 Uiso d R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Tm1 O1 . 2.361(7) ?
    Tm1 O8 6_554 2.363(7) ?
    Tm1 O5 . 2.364(7) ?
    Tm1 O3 6 2.371(7) ?
    Tm1 O10 . 2.434(7) ?
    Tm1 O9 . 2.448(7) ?
    Tm1 N2 . 2.536(8) ?
    Tm1 N1 . 2.546(8) ?
    C1 N2 . 1.341(12) ?
    C1 C2 . 1.381(13) ?
    C1 C6 . 1.528(12) ?
    C2 C3 . 1.380(14) ?
    C2 H2A . 0.930 ?
    C3 C4 . 1.376(13) ?
    C3 H3A . 0.930 ?
    C4 C5 . 1.392(13) ?
    C4 C7 . 1.506(14) ?
    C5 N2 . 1.359(13) ?
    C5 H5A . 0.930 ?
    C6 O2 . 1.230(12) ?
    C6 O1 . 1.268(11) ?
    C7 O4 . 1.217(13) ?
    C7 O3 . 1.284(12) ?
    C8 O6 . 1.221(12) ?
    C8 O5 . 1.246(12) ?
    C8 C9 . 1.529(13) ?
    C9 N1 . 1.360(12) ?
    C9 C10 . 1.390(13) ?
    C10 C11 . 1.347(15) ?
    C10 H10A . 0.930 ?
    C11 C12 . 1.438(13) ?
    C11 H11A . 0.930 ?
    C12 C13 . 1.363(13) ?
    C12 C14 . 1.502(13) ?
    C13 N1 . 1.338(13) ?
    C13 H13A . 0.930 ?
    C14 O7 . 1.215(13) ?
    C14 O8 . 1.287(12) ?
    O1 H1 . 0.850 ?
    O3 Tm1 6_554 2.371(7) ?
    O8 Tm1 6 2.363(7) ?
    O9 H91 . 0.850 ?
    O9 H92 . 0.850 ?
    O10 H101 . 0.850 ?
    O10 H102 . 0.850 ?
    O11 H111 . 0.850 ?
    O11 H112 . 0.850 ?
    O12 H121 . 0.850 ?
    O12 H122 . 0.850 ?
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
    O1 Tm1 O8 . 6_554 116.1(3) ?
    O1 Tm1 O5 . . 124.3(2) ?
    O8 Tm1 O5 6_554 . 83.6(2) ?
    O1 Tm1 O3 . 6 81.6(2) ?
    O8 Tm1 O3 6_554 6 140.4(2) ?
    O5 Tm1 O3 . 6 116.7(2) ?
    O1 Tm1 O10 . . 78.6(2) ?
    O8 Tm1 O10 6_554 . 76.8(2) ?
    O5 Tm1 O10 . . 155.2(2) ?
    O3 Tm1 O10 6 . 72.4(2) ?
    O1 Tm1 O9 . . 154.7(2) ?
    O8 Tm1 O9 6_554 . 78.1(2) ?
    O5 Tm1 O9 . . 76.1(2) ?
    O3 Tm1 O9 6 . 75.0(2) ?
    O10 Tm1 O9 . . 85.1(2) ?
    O1 Tm1 N2 . . 64.7(2) ?
    O8 Tm1 N2 6_554 . 73.3(3) ?
    O5 Tm1 N2 . . 74.1(3) ?
    O3 Tm1 N2 6 . 142.5(2) ?
    O10 Tm1 N2 . . 113.6(3) ?
    O9 Tm1 N2 . . 140.5(2) ?
    O1 Tm1 N1 . . 73.5(3) ?
    O8 Tm1 N1 6_554 . 144.7(3) ?
    O5 Tm1 N1 . . 65.1(3) ?
    O3 Tm1 N1 6 . 72.3(3) ?
    O10 Tm1 N1 . . 137.5(3) ?
    O9 Tm1 N1 . . 107.7(2) ?
    N2 Tm1 N1 . . 82.3(3) ?
    N2 C1 C2 . . 121.0(8) ?
    N2 C1 C6 . . 114.9(7) ?
    C2 C1 C6 . . 124.0(8) ?
    C3 C2 C1 . . 119.9(8) ?
    C3 C2 H2A . . 120.0 ?
    C1 C2 H2A . . 120.0 ?
    C4 C3 C2 . . 120.4(8) ?
    C4 C3 H3A . . 119.8 ?
    C2 C3 H3A . . 119.8 ?
    C3 C4 C5 . . 116.5(8) ?
    C3 C4 C7 . . 124.0(9) ?
    C5 C4 C7 . . 119.5(8) ?
    N2 C5 C4 . . 123.6(8) ?
    N2 C5 H5A . . 118.2 ?
    C4 C5 H5A . . 118.2 ?
    O2 C6 O1 . . 126.8(8) ?
    O2 C6 C1 . . 119.0(8) ?
    O1 C6 C1 . . 114.3(8) ?
    O4 C7 O3 . . 123.6(9) ?
    O4 C7 C4 . . 119.1(9) ?
    O3 C7 C4 . . 117.4(9) ?
    O6 C8 O5 . . 126.0(9) ?
    O6 C8 C9 . . 118.6(9) ?
    O5 C8 C9 . . 115.4(8) ?
    N1 C9 C10 . . 119.8(9) ?
    N1 C9 C8 . . 115.0(8) ?
    C10 C9 C8 . . 125.1(8) ?
    C11 C10 C9 . . 121.0(9) ?
    C11 C10 H10A . . 119.5 ?
    C9 C10 H10A . . 119.5 ?
    C10 C11 C12 . . 120.0(9) ?
    C10 C11 H11A . . 120.0 ?
    C12 C11 H11A . . 120.0 ?
    C13 C12 C11 . . 114.9(8) ?
    C13 C12 C14 . . 124.1(8) ?
    C11 C12 C14 . . 120.9(8) ?
    N1 C13 C12 . . 125.9(9) ?
    N1 C13 H13A . . 117.0 ?
    C12 C13 H13A . . 117.0 ?
    O7 C14 O8 . . 124.5(9) ?
    O7 C14 C12 . . 120.7(9) ?
    O8 C14 C12 . . 114.8(8) ?
    C13 N1 C9 . . 118.3(8) ?
    C13 N1 Tm1 . . 124.2(6) ?
    C9 N1 Tm1 . . 116.5(7) ?
    C1 N2 C5 . . 118.3(8) ?
    C1 N2 Tm1 . . 117.5(6) ?
    C5 N2 Tm1 . . 124.2(6) ?
    C6 O1 Tm1 . . 126.0(6) ?
    C6 O1 H1 . . 117.1 ?
    Tm1 O1 H1 . . 116.9 ?
    C7 O3 Tm1 . 6_554 141.4(6) ?
    C8 O5 Tm1 . . 127.5(6) ?
    C14 O8 Tm1 . 6 136.9(6) ?
    Tm1 O9 H91 . . 97.2 ?
    Tm1 O9 H92 . . 113.8 ?
    H91 O9 H92 . . 100.6 ?
    Tm1 O10 H101 . . 95.7 ?
    Tm1 O10 H102 . . 115.4 ?
    H101 O10 H102 . . 100.8 ?
    H111 O11 H112 . . 132.5 ?
    H121 O12 H122 . . 96.9 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N2 C1 C2 C3 . . . . -4.1(14) ?
    C6 C1 C2 C3 . . . . 173.5(8) ?
    C1 C2 C3 C4 . . . . 2.0(14) ?
    C2 C3 C4 C5 . . . . 2.3(13) ?
    C2 C3 C4 C7 . . . . -176.5(9) ?
    C3 C4 C5 N2 . . . . -5.0(14) ?
    C7 C4 C5 N2 . . . . 173.9(9) ?
    N2 C1 C6 O2 . . . . -170.7(9) ?
    C2 C1 C6 O2 . . . . 11.5(14) ?
    N2 C1 C6 O1 . . . . 10.3(11) ?
    C2 C1 C6 O1 . . . . -167.5(8) ?
    C3 C4 C7 O4 . . . . 0.1(14) ?
    C5 C4 C7 O4 . . . . -178.7(9) ?
    C3 C4 C7 O3 . . . . 178.9(9) ?
    C5 C4 C7 O3 . . . . 0.2(13) ?
    O6 C8 C9 N1 . . . . -172.2(8) ?
    O5 C8 C9 N1 . . . . 7.3(11) ?
    O6 C8 C9 C10 . . . . 10.7(13) ?
    O5 C8 C9 C10 . . . . -169.9(9) ?
    N1 C9 C10 C11 . . . . -2.3(13) ?
    C8 C9 C10 C11 . . . . 174.7(8) ?
    C9 C10 C11 C12 . . . . 2.3(14) ?
    C10 C11 C12 C13 . . . . -0.2(13) ?
    C10 C11 C12 C14 . . . . -177.1(9) ?
    C11 C12 C13 N1 . . . . -2.1(14) ?
    C14 C12 C13 N1 . . . . 174.7(9) ?
    C13 C12 C14 O7 . . . . 178.6(9) ?
    C11 C12 C14 O7 . . . . -4.8(14) ?
    C13 C12 C14 O8 . . . . -1.2(13) ?
    C11 C12 C14 O8 . . . . 175.4(8) ?
    C12 C13 N1 C9 . . . . 2.2(14) ?
    C12 C13 N1 Tm1 . . . . -166.1(7) ?
    C10 C9 N1 C13 . . . . 0.1(13) ?
    C8 C9 N1 C13 . . . . -177.2(8) ?
    C10 C9 N1 Tm1 . . . . 169.3(6) ?
    C8 C9 N1 Tm1 . . . . -8.0(9) ?
    O1 Tm1 N1 C13 . . . . -44.8(7) ?
    O8 Tm1 N1 C13 6_554 . . . -156.8(7) ?
    O5 Tm1 N1 C13 . . . . 173.4(8) ?
    O3 Tm1 N1 C13 6 . . . 41.5(7) ?
    O10 Tm1 N1 C13 . . . . 6.3(9) ?
    O9 Tm1 N1 C13 . . . . 108.7(7) ?
    N2 Tm1 N1 C13 . . . . -110.6(8) ?
    O1 Tm1 N1 C9 . . . . 146.7(7) ?
    O8 Tm1 N1 C9 6_554 . . . 34.7(9) ?
    O5 Tm1 N1 C9 . . . . 4.9(6) ?
    O3 Tm1 N1 C9 6 . . . -127.0(7) ?
    O10 Tm1 N1 C9 . . . . -162.2(6) ?
    O9 Tm1 N1 C9 . . . . -59.8(7) ?
    N2 Tm1 N1 C9 . . . . 80.9(6) ?
    C2 C1 N2 C5 . . . . 1.6(13) ?
    C6 C1 N2 C5 . . . . -176.2(8) ?
    C2 C1 N2 Tm1 . . . . 179.9(7) ?
    C6 C1 N2 Tm1 . . . . 2.1(10) ?
    C4 C5 N2 C1 . . . . 3.1(14) ?
    C4 C5 N2 Tm1 . . . . -175.1(7) ?
    O1 Tm1 N2 C1 . . . . -7.8(6) ?
    O8 Tm1 N2 C1 6_554 . . . -138.3(7) ?
    O5 Tm1 N2 C1 . . . . 133.7(7) ?
    O3 Tm1 N2 C1 6 . . . 20.3(9) ?
    O10 Tm1 N2 C1 . . . . -71.3(7) ?
    O9 Tm1 N2 C1 . . . . 176.1(6) ?
    N1 Tm1 N2 C1 . . . . 67.5(7) ?
    O1 Tm1 N2 C5 . . . . 170.3(8) ?
    O8 Tm1 N2 C5 6_554 . . . 39.8(8) ?
    O5 Tm1 N2 C5 . . . . -48.2(8) ?
    O3 Tm1 N2 C5 6 . . . -161.6(7) ?
    O10 Tm1 N2 C5 . . . . 106.8(8) ?
    O9 Tm1 N2 C5 . . . . -5.7(10) ?
    N1 Tm1 N2 C5 . . . . -114.3(8) ?
    O2 C6 O1 Tm1 . . . . 161.1(8) ?
    C1 C6 O1 Tm1 . . . . -20.0(11) ?
    O8 Tm1 O1 C6 6_554 . . . 69.8(7) ?
    O5 Tm1 O1 C6 . . . . -30.8(8) ?
    O3 Tm1 O1 C6 6 . . . -147.5(7) ?
    O10 Tm1 O1 C6 . . . . 138.9(7) ?
    O9 Tm1 O1 C6 . . . . -170.2(6) ?
    N2 Tm1 O1 C6 . . . . 15.6(7) ?
    N1 Tm1 O1 C6 . . . . -73.6(7) ?
    O4 C7 O3 Tm1 . . . 6_554 14.3(17) ?
    C4 C7 O3 Tm1 . . . 6_554 -164.4(7) ?
    O6 C8 O5 Tm1 . . . . 176.6(7) ?
    C9 C8 O5 Tm1 . . . . -2.8(11) ?
    O1 Tm1 O5 C8 . . . . -46.8(8) ?
    O8 Tm1 O5 C8 6_554 . . . -164.2(8) ?
    O3 Tm1 O5 C8 6 . . . 51.6(8) ?
    O10 Tm1 O5 C8 . . . . 158.1(7) ?
    O9 Tm1 O5 C8 . . . . 116.5(8) ?
    N2 Tm1 O5 C8 . . . . -89.7(7) ?
    N1 Tm1 O5 C8 . . . . -0.9(7) ?
    O7 C14 O8 Tm1 . . . 6 23.9(16) ?
    C12 C14 O8 Tm1 . . . 6 -156.4(6) ?
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
    O1 H1 O12 7 0.85 1.97 2.788(11) 162.0
    O9 H91 O4 6 0.85 1.83 2.679(10) 179.9
    O9 H92 O4 4_655 0.85 1.99 2.842(10) 179.6
    O10 H101 O7 6_554 0.85 1.83 2.675(11) 179.3
    O10 H102 O9 7 0.85 2.14 2.996(10) 179.1
    O11 H111 O5 . 0.85 2.02 2.872(11) 179.4
    O11 H112 O2 6_554 0.85 1.91 2.763(11) 179.8
    O12 H121 O6 2 0.85 2.15 3.004(12) 179.3
    O12 H122 O6 3 0.85 2.08 2.933(12) 179.4
