##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.0.1.  #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_journal_date_recd_electronic     2000-02-04
_journal_date_accepted     2000-05-09
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      8
_journal_page_first     1021
_journal_page_last     1023
_journal_paper_category     FO
_publ_contact_author_name     'Dr. Roger E. Gerkin'
_publ_contact_author_address
;
Department of Chemistry
The Ohio State University
Columbus, Ohio  43210, USA
;
_publ_contact_author_email     'gerkin@chemistry.ohio-state.edu'
_publ_contact_author_fax     '614 292 1685'
_publ_contact_author_phone     '614 292 6053'
_publ_section_title
; Hydrogen bonding and C-H...O interactions in 3-(3-aminophthalimido)phthalic
acid dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Dobson, Allison J.'
;Department of Chemistry
The Ohio State University
Columbus, Ohio  43210, USA
;
    'Gerkin, Roger E.'
;Department of Chemistry
The Ohio State University
Columbus, Ohio  43210, USA
;
data_I
_chemical_name_systematic
; ?
;
_chemical_name_common
;3-(3-aminophthalimido)phthalic acid dihydrate
#
;
_chemical_formula_moiety     'C16 H10 N2 O6 , 2H2 O'
_chemical_formula_sum     'C16 H14 N2 O8'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     362.30
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     ?
loop_
    _symmetry_equiv_pos_as_xyz
    '   +x,   +y,   +z'
    '   -x,   -y,   -z'
_cell_length_a     7.5608(2)
_cell_length_b     9.0632(2)
_cell_length_c     12.7245(3)
_cell_angle_alpha     69.4810(10)
_cell_angle_beta     82.7640(10)
_cell_angle_gamma     76.229(2)
_cell_volume     792.29(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     20808
_cell_measurement_theta_min     1.71
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     150
_exptl_crystal_description     'uncut plate '
_exptl_crystal_colour     'yellow-orange (golden)'
_exptl_crystal_size_max      .31
_exptl_crystal_size_mid      .23
_exptl_crystal_size_min      .08
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.519
_exptl_crystal_density_meas     ' not measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu      .124
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
; The Laue group assignment, and the centrosymmetry indicated by the intensity
statistics led to assignment of the space group as P-1 (No. 2); since refinement
proceeded well, it was adopted. Fourier difference methods were used to locate
initial H atom positions, and these H atoms were refined. Refined C-H distances
ranged from 0.92(2) to 1.00(1) Å, with mean value 0.96(3) Å; their Uiso
values ranged from 0.4 to 1.4 times the Ueq values of the attached C atoms.
These H atoms were then made canonical, with C-H = 0.98 Å and Uiso = 1.2
× Ueq of the attached C atom. In the later stages of refinement the
extinction coefficient was predicted to be negative, so was not included in the
model. One reflection, 2 2 1, was removed early in the refinement since it was
grossly deviant. The maximum peak in the final difference map occurs ∼ 1.2
Å from O8, but not in a position to be a potential H atom, the maximum
negative peak ∼ 0.8 Å from O6.
;
_diffrn_ambient_temperature     150
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD diffractometer'
_diffrn_measurement_method     'omega scans with κ offsets'
_diffrn_reflns_number     20808
_diffrn_reflns_av_R_equivalents      .037
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     ?
_diffrn_measured_fraction_theta_max      .999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_reflns_reduction_process     ?
_refine_special_details
; ?
;
_reflns_number_total     3628
_reflns_number_gt     2917
_reflns_threshold_expression     'I > 2σI'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     ?
_refine_ls_R_factor_gt      .049
_refine_ls_wR_factor_ref      .125
_refine_ls_goodness_of_fit_ref     1.98
_refine_ls_restrained_S_all     ?
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     3627
_refine_ls_number_parameters     267
_refine_ls_number_restraints     ?
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     'mixed'
_refine_ls_weighting_scheme     sigma
_refine_ls_weighting_details     'w = 1/[σ²cs + (0.037I)²]'
_refine_ls_shift/su_max      .0004
_refine_ls_shift/esd_mean     ?
_refine_diff_density_max      .59
_refine_diff_density_min      -.33
_refine_ls_extinction_method     ' none'
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    H ? 0 0 'Stewart, Davidson and Simpson (1965)'
    C ?  .003  .002 'Creagh & McAuley (1992)'
    O ?  .011  .006 'Creagh & McAuley (1992)'
    N ?  .006  .003 'Creagh & McAuley (1992)'
_computing_data_collection
;  COLLECT (Nonius, 1999)
;
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1990)'
_computing_structure_refinement
                                'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'TEXSAN and  PLATON (Spek, 1990)'
loop_
    _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_calc_attached_atom
    _atom_site_refinement_flags
    _atom_site_occupancy
    O1  .7732(2)  .64920(10)
                            .21581(9)  .0317(3) Uani d ? . 1.000
    O2  .42370(10)
                  .91180(10)
                            .44394(9)  .0300(3) Uani d ? . 1.000
    O3  .8102(2) 1.08790(10)
                            .30240(10)
                                      .0353(3) Uani d ? . 1.000
    O4  .9659(2)  .94470(10)
                            .19580(10)
                                      .0355(3) Uani d ? . 1.000
    O5  .6786(2) 1.42200(10)
                            -.07808(9)  .0319(3) Uani d ? . 1.000
    O6  .8605(2) 1.30330(10)
                            .06540(10)
                                      .0431(4) Uani d ? . 1.000
    O7 1.0642(2) 1.42150(10)
                            .17240(10)
                                      .0299(3) Uani d ? . 1.000
    O8 1.1062(2) 1.12880(10)
                            .36340(10)
                                      .0376(4) Uani d ? . 1.000
    N1  .5299(2)  .6613(2)  .67460(10)
                                      .0383(4) Uani d ? . 1.000
    N2  .5906(2)  .81650(10)
                            .30610(10)
                                      .0230(3) Uani d ? . 1.000
    C1  .7352(2)  .5683(2)  .42090(10)
                                      .0241(4) Uani d ? . 1.000
    C2  .6318(2)  .6519(2)  .48900(10)
                                      .0236(4) Uani d ? . 1.000
    C3  .6284(2)  .5833(2)  .60630(10)
                                      .0266(4) Uani d ? . 1.000
    C4  .7367(2)  .4264(2)  .64860(10)
                                      .0301(4) Uani d ? . 1.000
    C5  .8355(2)  .3464(2)  .57940(10)
                                      .0306(4) Uani d ? . 1.000
    C6  .8371(2)  .4148(2)  .46300(10)
                                      .0285(4) Uani d ? . 1.000
    C7  .7095(2)  .6740(2)  .30220(10)
                                      .0244(4) Uani d ? . 1.000
    C8  .5342(2)  .8075(2)  .41810(10)
                                      .0236(4) Uani d ? . 1.000
    C9  .5361(2)  .9554(2)  .20880(10)
                                      .0225(4) Uani d ? . 1.000
    C10  .6517(2) 1.0634(2)  .16390(10)
                                       .0224(4) Uani d ? . 1.000
    C11  .6008(2) 1.1972(2)  .06850(10)
                                       .0233(4) Uani d ? . 1.000
    C12  .4358(2) 1.2210(2)  .02100(10)
                                       .0250(4) Uani d ? . 1.000
    C13  .3205(2) 1.1145(2)  .06800(10)
                                       .0265(4) Uani d ? . 1.000
    C14  .3710(2)  .9807(2)  .16240(10)
                                       .0258(4) Uani d ? . 1.000
    C15  .8291(2) 1.0276(2)  .21980(10)
                                       .0250(4) Uani d ? . 1.000
    C16  .7251(2) 1.3119(2)  .01960(10)
                                       .0257(4) Uani d ? . 1.000
    H1N1  .446(3)  .759(3)  .642(2)  .059(6) Uiso d ? . 1.000
    H1  .933(3) 1.083(3)  .330(2)  .075(7) Uiso d ? . 1.000
    H1O7  .975(3) 1.488(3)  .184(2)  .060(7) Uiso d ? . 1.000
    H1O8 1.227(4) 1.039(3)  .398(2)  .096(9) Uiso d ? . 1.000
    H2N1  .519(3)  .601(3)  .753(2)  .061(6) Uiso d ? . 1.000
    H2O7 1.011(3) 1.387(2)  .125(2)  .051(6) Uiso d ? . 1.000
    H2  .762(3) 1.478(2)  -.102(2)  .044(6) Uiso d ? . 1.000
    H2O8 1.138(5) 1.224(4)  .301(3)  .130(10)
                                            Uiso d ? . 1.000
    H4  .7412  .3730  .7301  .036 Uiso c ? . 1.000
    H5  .9073  .2375  .6131  .037 Uiso c ? . 1.000
    H6  .9070  .3569  .4139  .034 Uiso c ? . 1.000
    H12  .4009 1.3142  -.0464  .030 Uiso c ? . 1.000
    H13  .2036 1.1333  .0349  .032 Uiso c ? . 1.000
    H14  .2901  .9046  .1958  .031 Uiso c ? . 1.000
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
    O1  .0330(6)  .0313(6)  .0264(6)  -.0006(5)  -.0007(5)  -.0087(5)
    O2  .0287(6)  .0289(6)  .0310(6)  -.0010(5)  -.0028(5)  -.0109(5)
    O3  .0279(7)  .0470(7)  .0327(7)  -.0031(5)  -.0081(5)  -.0161(6)
    O4  .0210(6)  .0403(7)  .0447(8)  -.0034(5)  -.0037(5)  -.0148(6)
    O5  .0312(7)  .0328(6)  .0264(6)  -.0123(5)  -.0051(5)  .0017(5)
    O6  .0447(8)  .0431(7)  .0380(7)  -.0232(6)  -.0180(6)  .0053(6)
    O7  .0271(7)  .0293(6)  .0322(7)  -.0064(5)  -.0012(5)  -.0087(5)
    O8  .0322(7)  .0347(7)  .0434(8)  -.0031(5)  -.0086(6)  -.0102(6)
    N1  .0412(9)  .0399(9)  .0286(9)  -.0012(7)  -.0027(7)  -.0093(7)
    N2  .0214(7)  .0214(6)  .0224(7)  -.0027(5)  -.0019(5)  -.0035(5)
    C1  .0206(8)  .0256(8)  .0258(8)  -.0073(6)  -.0030(6)  -.0056(7)
    C2  .0214(8)  .0245(8)  .0242(8)  -.0071(6)  -.0057(6)  -.0041(7)
    C3  .0251(8)  .0302(8)  .0259(9)  -.0097(7)  -.0032(7)  -.0077(7)
    C4  .0327(9)  .0284(8)  .0248(9)  -.0100(7)  -.0094(7)  .0017(7)
    C5  .0307(9)  .0238(8)  .0340(10)
                                     -.0065(7)  -.0102(7)  -.0014(7)
    C6  .0259(8)  .0248(8)  .0319(9)  -.0050(6)  -.0071(7)  -.0040(7)
    C7  .0195(8)  .0249(8)  .0279(9)  -.0045(6)  -.0036(6)  -.0070(7)
    C8  .0213(8)  .0259(8)  .0249(8)  -.0083(6)  -.0019(6)  -.0076(7)
    C9  .0217(8)  .0224(8)  .0200(8)  -.0009(6)  -.0024(6)  -.0049(6)
    C10  .0198(8)  .0240(8)  .0221(8)  -.0019(6)  -.0016(6)  -.0077(6)
    C11  .0237(8)  .0231(8)  .0216(8)  -.0033(6)  -.0026(6)  -.0060(7)
    C12  .0251(8)  .0253(8)  .0216(8)  -.0013(6)  -.0036(6)  -.0061(6)
    C13  .0195(8)  .0298(8)  .0281(9)  -.0022(6)  -.0052(7)  -.0079(7)
    C14  .0202(8)  .0259(8)  .0301(9)  -.0048(6)  -.0007(6)  -.0080(7)
    C15  .0249(9)  .0228(8)  .0232(8)  -.0067(6)  -.0018(6)  -.0011(7)
    C16  .0289(9)  .0241(8)  .0221(8)  -.0064(6)  -.0045(7)  -.0035(7)
_geom_special_details
;
                       Table of Least-Squares Planes
                       ------------------------------
               -------------- Plane number  1 ---------------
               Atoms Defining Plane      Distance      esd
                        C1     (    1)     0.0067      0.0014
                        C2     (    1)    -0.0016      0.0014
                        C3     (    1)    -0.0045      0.0015
                        C4     (    1)     0.0066      0.0016
                        C5     (    1)     0.0000      0.0016
                        C6     (    1)    -0.0068      0.0015
               Mean deviation from plane is 0.0044  angstroms
                Chi-squared:        75.5
               -------------- Plane number  2 ---------------
               Atoms Defining Plane      Distance      esd
                        C1     (    1)    -0.0055      0.0014
                        C2     (    1)     0.0138      0.0014
                        C7     (    1)    -0.0060      0.0014
                        C8     (    1)    -0.0186      0.0014
                        N2     (    1)     0.0115      0.0012
               Additional Atoms          Distance
                        O1     (    1)    -0.0264
                        O2     (    1)    -0.0829
               Mean deviation from plane is 0.0111  angstroms
                Chi-squared:       417.4
               Dihedral angles between least-squares planes
                            plane  plane   angle
                              2      1      1.13
               -------------- Plane number  3 ---------------
               Atoms Defining Plane      Distance      esd
                        O1     (    1)    -0.0214      0.0012
                        O2     (    1)    -0.0292      0.0011
                        N2     (    1)     0.0466      0.0012
                        C1     (    1)    -0.0143      0.0014
                        C2     (    1)     0.0201      0.0014
                        C7     (    1)     0.0037      0.0014
                        C8     (    1)     0.0156      0.0014
               Mean deviation from plane is 0.0216  angstroms
                Chi-squared:      3147.4
               Dihedral angles between least-squares planes
                            plane  plane   angle
                              3      1      2.03
                              3      2      1.13
               -------------- Plane number  4 ---------------
               Atoms Defining Plane      Distance      esd
                        C1     (    1)     0.0032      0.0014
                        C2     (    1)     0.0068      0.0014
                        C3     (    1)     0.0088      0.0015
                        C4     (    1)     0.0118      0.0016
                        C5     (    1)    -0.0065      0.0016
                        C6     (    1)    -0.0179      0.0015
                        C7     (    1)     0.0076      0.0014
                        C8     (    1)    -0.0312      0.0014
                        N2     (    1)     0.0118      0.0012
               Additional Atoms          Distance
                        O1     (    1)    -0.0003
                        O2     (    1)    -0.1082
               Mean deviation from plane is 0.0117  angstroms
                Chi-squared:       867.8
               Dihedral angles between least-squares planes
                            plane  plane   angle
                              4      1      0.49
                              4      2      0.64
                              4      3      1.59
               -------------- Plane number  5 ---------------
               Atoms Defining Plane      Distance      esd
                        C9     (    1)     0.0092      0.0014
                        C10    (    1)    -0.0073      0.0014
                        C11    (    1)    -0.0006      0.0014
                        C12    (    1)     0.0075      0.0015
                        C13    (    1)    -0.0059      0.0015
                        C14    (    1)    -0.0029      0.0015
               Mean deviation from plane is 0.0056  angstroms
                Chi-squared:       111.7
               Dihedral angles between least-squares planes
                            plane  plane   angle
                              5      1     96.02
                              5      2     97.15
                              5      3     97.76
                              5      4     96.51
               -------------- Plane number  6 ---------------
               Atoms Defining Plane      Distance      esd
                        C15    (    1)     0.0000
                        O3     (    1)     0.0000
                        O4     (    1)     0.0000
               Mean deviation from plane is 0.0000  angstroms
                Chi-squared:         0.0
               Dihedral angles between least-squares planes
                            plane  plane   angle
                              6      1    130.49
                              6      2    130.49
                              6      3    131.38
                              6      4    130.53
                              6      5     88.90
               -------------- Plane number  7 ---------------
               Atoms Defining Plane      Distance      esd
                        O5     (    1)     0.0000
                        O6     (    1)     0.0000
                        C16    (    1)     0.0000
               Mean deviation from plane is 0.0000  angstroms
                Chi-squared:         0.0
               Dihedral angles between least-squares planes
                            plane  plane   angle
                              7      1     87.02
                              7      2     85.89
                              7      3     85.15
                              7      4     86.53
                              7      5    171.44
                              7      6     95.21
The C1-C6 ring is closely planar, the maximum deviation of any of its atoms from
the best-fit plane describing them being 0.007(2) Å. The dihedral angle
between this plane and the amino-group plane is 18(1) °. The dihedral
angle between these two planes is 0.4(1) °. The phthalimide core, atoms C1-C8
and N2, is described by a best-fit plane from which their maximum deviation is
0.032(2) Å. The C9-C14 phenyl ring is also closely planar, the maximum
deviation of any of its atoms from the best-fit plane describing them being
0.009(2) Å. The dihedral angle between this latter plane and the phthalimide
core plane is 83.5(1) °, between it and the plane of carboxyl group C15-O3-O4
is 88.9(2) ° , and between it and the plane of carboxyl group C16-O5-O6 is
8.6(2) °. These features can be seen in the packing diagram, Fig. 2.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . . 1.217(2) yes
    O2 C8 . . 1.213(2) yes
    O3 C15 . . 1.323(2) yes
    O3 H1 . . 1.02(3) no
    O4 C15 . . 1.200(2) yes
    O5 C16 . . 1.318(2) yes
    O5 H2 . .  .86(2) no
    O6 C16 . . 1.214(2) yes
    O7 H1O7 . .  .83(2) no
    O7 H2O7 . .  .93(2) no
    O8 H1O8 . . 1.09(3) no
    O8 H2O8 . . 1.00(3) no
    N1 C3 . . 1.352(2) yes
    N1 H1N1 . .  .95(2) no
    N1 H2N1 . .  .96(2) no
    N2 C7 . . 1.399(2) yes
    N2 C8 . . 1.415(2) yes
    N2 C9 . . 1.441(2) yes
    C1 C2 . . 1.395(2) no
    C1 C6 . . 1.374(2) no
    C1 C7 . . 1.485(2) no
    C2 C3 . . 1.401(2) no
    C2 C8 . . 1.458(2) no
    C3 C4 . . 1.415(2) no
    C4 C5 . . 1.372(2) no
    C4 H4 . .  .98 no
    C5 C6 . . 1.390(2) no
    C5 H5 . .  .98 no
    C6 H6 . .  .98 no
    C9 C10 . . 1.393(2) no
    C9 C14 . . 1.383(2) no
    C10 C11 . . 1.398(2) no
    C10 C15 . . 1.511(2) no
    C11 C12 . . 1.392(2) no
    C11 C16 . . 1.489(2) no
    C12 C13 . . 1.383(2) no
    C12 H12 . .  .98 no
    C13 C14 . . 1.390(2) no
    C13 H13 . .  .98 no
    C14 H14 . .  .98 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C15 O3 H1 . . . 112.0(10)
                           no
    C16 O5 H2 . . . 108.0(10)
                           no
    H1O7 O7 H2O7 . . . 99(2) no
    H1O8 O8 H2O8 . . . 112(2) no
    C3 N1 H1N1 . . . 118.0(10)
                            no
    C3 N1 H2N1 . . . 118.0(10)
                            no
    H1N1 N1 H2N1 . . . 121(2) no
    C7 N2 C8 . . . 111.10(10)
                            yes
    C7 N2 C9 . . . 124.40(10)
                            yes
    C8 N2 C9 . . . 124.50(10)
                            yes
    C2 C1 C6 . . . 123.00(10)
                            no
    C2 C1 C7 . . . 107.60(10)
                            no
    C6 C1 C7 . . . 129.40(10)
                            no
    C1 C2 C3 . . . 121.20(10)
                            no
    C1 C2 C8 . . . 109.10(10)
                            no
    C3 C2 C8 . . . 129.70(10)
                            no
    N1 C3 C2 . . . 122.6(2) yes
    N1 C3 C4 . . . 122.2(2) yes
    C2 C3 C4 . . . 115.20(10)
                            no
    C3 C4 C5 . . . 122.20(10)
                            no
    C3 C4 H4 . . . 118.9 no
    C5 C4 H4 . . . 118.9 no
    C4 C5 C6 . . . 122.20(10)
                            no
    C4 C5 H5 . . . 118.9 no
    C6 C5 H5 . . . 118.9 no
    C1 C6 C5 . . . 116.10(10)
                            no
    C1 C6 H6 . . . 121.9 no
    C5 C6 H6 . . . 121.9 no
    O1 C7 N2 . . . 124.10(10)
                            yes
    O1 C7 C1 . . . 129.80(10)
                            no
    N2 C7 C1 . . . 106.10(10)
                            no
    O2 C8 N2 . . . 124.10(10)
                            yes
    O2 C8 C2 . . . 129.90(10)
                            no
    N2 C8 C2 . . . 106.00(10)
                            no
    N2 C9 C10 . . . 118.60(10)
                             no
    N2 C9 C14 . . . 120.20(10)
                             no
    C10 C9 C14 . . . 121.10(10)
                              no
    C9 C10 C11 . . . 118.90(10)
                              no
    C9 C10 C15 . . . 117.90(10)
                              no
    C11 C10 C15 . . . 123.20(10)
                               no
    C10 C11 C12 . . . 119.80(10)
                               no
    C10 C11 C16 . . . 119.00(10)
                               no
    C12 C11 C16 . . . 121.20(10)
                               no
    C11 C12 C13 . . . 120.60(10)
                               no
    C11 C12 H12 . . . 119.7 no
    C13 C12 H12 . . . 119.7 no
    C12 C13 C14 . . . 119.80(10)
                               no
    C12 C13 H13 . . . 120.1 no
    C14 C13 H13 . . . 120.1 no
    C9 C14 C13 . . . 119.70(10)
                              no
    C9 C14 H14 . . . 120.2 no
    C13 C14 H14 . . . 120.2 no
    O3 C15 O4 . . . 125.10(10)
                             yes
    O3 C15 C10 . . . 111.90(10)
                              yes
    O4 C15 C10 . . . 122.80(10)
                              yes
    O5 C16 O6 . . . 122.50(10)
                             yes
    O5 C16 C11 . . . 114.90(10)
                              yes
    O6 C16 C11 . . . 122.50(10)
                              yes
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
    O1 C7 N2 C8 . . . . 177.70(10)
                                 no
    O1 C7 N2 C9 . . . . -3.5(2) no
    O1 C7 C1 C2 . . . . -179.6(2) no
    O1 C7 C1 C6 . . . .  -.4(3) no
    O2 C8 N2 C7 . . . . -175.90(10)
                                  no
    O2 C8 N2 C9 . . . . 5.4(2) no
    O2 C8 C2 C1 . . . . 175.80(10)
                                 no
    O2 C8 C2 C3 . . . . -2.4(3) no
    O3 C15 C10 C9 . . . . -88.0(2) no
    O3 C15 C10 C11 . . . . 93.4(2) no
    O4 C15 C10 C9 . . . . 87.3(2) no
    O4 C15 C10 C11 . . . . -91.3(2) no
    O5 C16 C11 C10 . . . . 171.40(10)
                                    no
    O5 C16 C11 C12 . . . . -8.6(2) no
    O6 C16 C11 C10 . . . . -7.6(2) no
    O6 C16 C11 C12 . . . . 172.4(2) no
    N1 C3 C2 C1 . . . . 179.90(10)
                                 no
    N1 C3 C2 C8 . . . . -2.1(3) no
    N1 C3 C4 C5 . . . . 179.4(2) no
    N2 C7 C1 C2 . . . .  -.1(2) no
    N2 C7 C1 C6 . . . . 179.10(10)
                                 no
    N2 C8 C2 C1 . . . . -2.9(2) no
    N2 C8 C2 C3 . . . . 178.90(10)
                                 no
    N2 C9 C10 C11 . . . . 179.10(10)
                                   no
    N2 C9 C10 C15 . . . .  .4(2) no
    N2 C9 C14 C13 . . . . -179.50(10)
                                    no
    C1 C2 C3 C4 . . . .  .2(2) no
    C1 C6 C5 C4 . . . .  .6(2) no
    C1 C7 N2 C8 . . . . -1.8(2) no
    C1 C7 N2 C9 . . . . 176.90(10)
                                 no
    C2 C1 C6 C5 . . . . -1.4(2) no
    C2 C3 C4 C5 . . . . -1.0(2) no
    C2 C8 N2 C7 . . . . 2.9(2) no
    C2 C8 N2 C9 . . . . -175.80(10)
                                  no
    C3 C2 C1 C6 . . . . 1.0(2) no
    C3 C2 C1 C7 . . . . -179.80(10)
                                  no
    C3 C4 C5 C6 . . . .  .6(2) no
    C4 C3 C2 C8 . . . . 178.20(10)
                                 no
    C5 C6 C1 C7 . . . . 179.60(10)
                                 no
    C6 C1 C2 C8 . . . . -177.40(10)
                                  no
    C7 N2 C9 C10 . . . . -82.3(2) no
    C7 N2 C9 C14 . . . . 98.4(2) no
    C7 C1 C2 C8 . . . . 1.9(2) no
    C8 N2 C9 C10 . . . . 96.2(2) no
    C8 N2 C9 C14 . . . . -83.0(2) no
    C9 C10 C11 C12 . . . .  .7(2) no
    C9 C10 C11 C16 . . . . -179.30(10)
                                     no
    C9 C14 C13 C12 . . . .  .2(2) no
    C10 C9 C14 C13 . . . . 1.2(2) no
    C10 C11 C12 C13 . . . .  .7(2) no
    C11 C10 C9 C14 . . . . -1.7(2) no
    C11 C12 C13 C14 . . . . -1.2(2) no
    C12 C11 C10 C15 . . . . 179.30(10)
                                     no
    C13 C12 C11 C16 . . . . -179.30(10)
                                      no
    C14 C9 C10 C15 . . . . 179.70(10)
                                    no
    C15 C10 C11 C16 . . . .  -.7(2) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O3 H1 O8 ? ? ? 1.02(3) 1.61(3) 2.604(2) 164(2) yes
    O8 H1O8 O2 ? ? 1_655 1.09(3) 1.68(3) 2.764(2) 175(2) yes
    O5 H2 O7 ? ? 2_785  .86(2) 1.75(2) 2.602(2) 169(2) yes
    O7 H2O7 O6 ? ? ?  .93(2) 1.87(2) 2.776(2) 164(2) yes
    O7 H1O7 O1 ? ? 1_565  .83(2) 1.95(2) 2.782(2) 177(2) yes
    O8 H2O8 O7 ? ? ? 1.00(3) 1.98(3) 2.884(2) 150(3) yes
    N1 H1N1 O3 ? ? 2_676  .95(2) 2.29(2) 3.059(2) 137(2) yes
    N1 H2N1 O5 ? ? 1_546  .96(2) 2.45(2) 3.289(2) 147(2) yes
    N1 H1N1 O2 ? ? ?  .95(2) 2.41(2) 3.077(2) 127(2) yes
    C14 H14 O4 ? ? 1_455  .98 2.39 3.118(2) 131 yes
    C6 H6 O8 ? ? 1_545  .98 2.48 3.408(2) 157 yes
    C12 H12 O1 ? ? 2_675  .98 2.55 3.285(2) 132 yes
    C5 H5 O4 ? ? 2_766  .98 2.57 3.363(2) 139 yes
    C4 H4 O5 ? ? 1_546  .98 2.60 3.438(2) 144 yes
    C13 H13 O6 ? ? 1_455  .98 2.74 3.490(2) 134 yes
