##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'APEX2 v2014.11-0'
_journal_date_recd_electronic     2016-01-22
_journal_date_accepted     2016-02-10
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      2
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616002522
_journal_coeditor_code     RZ4001
_publ_contact_author_name     'Takashiro Akitsu'
_publ_contact_author_address
;
Department of Chemistry
Faculty of Science
Tokyo University of Science
1-3 Kagurazaka
Shinjuku-ku
Tokyo 162-8601
Japan
;
_publ_contact_author_email     akitsu@rs.kagu.tus.ac.jp
_publ_contact_author_fax     '(81) 3 5228 8271'
_publ_contact_author_phone     '(81) 3 5261 4631'
_publ_section_title
;
4,4'-(1,2-Diazaniumylethane-1,2-diyl)dibenzoate trihydrate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Numata, Takashi'
;
Department of Chemistry
Faculty of Science
Tokyo University of Science
1-3 Kagurazaka
Shinjuku-ku
Tokyo 162-8601
Japan
;
    'Ikenomoto, Shun'
;
Department of Chemistry
Faculty of Science
Tokyo University of Science
1-3 Kagurazaka
Shinjuku-ku
Tokyo 162-8601
Japan
;
    'Akitsu, Takashiro'
;
Department of Chemistry
Faculty of Science
Tokyo University of Science
1-3 Kagurazaka
Shinjuku-ku
Tokyo 162-8601
Japan
;
_publ_section_synopsis
;
The molecule is a double zwitterion with two of the carboxylic acid H atoms
transferred to the two N atoms. Intermolecular N---H...O and O---H...O
hydrogen bond involving the ammonium groups, the carboxylate groups and the
water molecules are observed.
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1452936'
_chemical_name_systematic
;
4,4'-(1,2-Diazaniumylethane-1,2-diyl)dibenzoate trihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N2 O4, 3(H2 O)'
_chemical_formula_sum     'C16 H22 N2 O7'
_chemical_formula_iupac     'C16 H16 N2 O4, 3H2 O'
_chemical_formula_weight     354.35
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P 1'
_space_group_name_Hall     'P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
_cell_length_a     6.778(3)
_cell_length_b     6.953(3)
_cell_length_c     9.458(4)
_cell_angle_alpha     109.182(6)
_cell_angle_beta     93.369(6)
_cell_angle_gamma     98.437(6)
_cell_volume     413.7(3)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     2325
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     27.54
_cell_measurement_temperature     173
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.491
_exptl_crystal_size_mid     0.342
_exptl_crystal_size_min     0.074
_exptl_crystal_density_diffrn     1.422
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     188
_exptl_absorpt_coefficient_mu     0.112
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.946
_exptl_absorpt_correction_T_max     0.990
_exptl_special_details
;
;
_diffrn_ambient_temperature     173
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     ?
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.333
_diffrn_reflns_number     2325
_diffrn_reflns_av_R_equivalents     0.0194
_diffrn_reflns_theta_min     2.29
_diffrn_reflns_theta_max     27.54
_diffrn_reflns_theta_full     27.54
_diffrn_measured_fraction_theta_max     0.948
_diffrn_measured_fraction_theta_full     0.948
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     6
_refine_special_details
;
;
_reflns_number_total     2030
_reflns_number_gt     1969
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0394
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.1009
_refine_ls_wR_factor_ref     0.1025
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     2030
_refine_ls_number_parameters     253
_refine_ls_number_restraints     3
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0632P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.372
_refine_diff_density_min     -0.214
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick 2015)
;
_refine_ls_extinction_coef     0.061(11)
_refine_ls_abs_structure_details
;
Flack x determined using 217 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     -0.2(10)
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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.2668(4) -0.0431(4) 0.0660(3) 0.0148(5) Uani d 1 . .
    C C14 0.6379(4) 0.5409(4) 1.0399(3) 0.0186(6) Uani d 1 . .
    H H14 0.7642 0.6159 1.0928 0.022 Uiso calc 1 . .
    C C10 0.4424(4) 0.3099(4) 0.8089(3) 0.0150(5) Uani d 1 . .
    C C13 0.4672(4) 0.5516(4) 1.1153(3) 0.0154(5) Uani d 1 . .
    C C4 0.4811(4) 0.1770(4) 0.2925(3) 0.0165(5) Uani d 1 . .
    H H4 0.6097 0.2517 0.3405 0.02 Uiso calc 1 . .
    C C15 0.6259(4) 0.4219(4) 0.8886(3) 0.0180(5) Uani d 1 . .
    H H15 0.7439 0.4169 0.8389 0.022 Uiso calc 1 . .
    C C9 0.4215(4) 0.1817(4) 0.6422(3) 0.0155(5) Uani d 1 . .
    H H9 0.3206 0.054 0.6262 0.019 Uiso calc 1 . .
    C C1 0.2389(4) -0.1709(4) -0.1001(3) 0.0177(5) Uani d 1 . .
    C C12 0.2827(4) 0.4406(4) 1.0366(3) 0.0166(5) Uani d 1 . .
    H H12 0.1651 0.4459 1.0866 0.02 Uiso calc 1 . .
    C C8 0.3387(4) 0.2978(4) 0.5438(3) 0.0145(5) Uani d 1 . .
    H H8 0.2001 0.3148 0.5703 0.017 Uiso calc 1 . .
    C C6 0.1036(4) -0.0325(4) 0.1485(3) 0.0189(6) Uani d 1 . .
    H H6 -0.0263 -0.1009 0.0992 0.023 Uiso calc 1 . .
    C C5 0.1280(4) 0.0772(4) 0.3027(3) 0.0188(6) Uani d 1 . .
    H H5 0.0154 0.0814 0.3582 0.023 Uiso calc 1 . .
    C C3 0.4556(4) 0.0630(4) 0.1388(3) 0.0156(5) Uani d 1 . .
    H H3 0.5681 0.0577 0.0831 0.019 Uiso calc 1 . .
    C C16 0.4895(4) 0.6773(4) 1.2817(3) 0.0167(5) Uani d 1 . .
    C C11 0.2706(4) 0.3217(4) 0.8846(3) 0.0170(5) Uani d 1 . .
    H H11 0.1441 0.2476 0.8315 0.02 Uiso calc 1 . .
    C C7 0.3178(4) 0.1811(4) 0.3758(3) 0.0151(5) Uani d 1 . .
    O O4 0.0625(3) -0.2489(3) -0.1609(2) 0.0281(5) Uani d 1 . .
    O O1 0.6571(3) 0.7863(3) 1.3418(2) 0.0245(5) Uani d 1 . .
    O O3 0.3929(3) -0.1941(3) -0.1665(2) 0.0240(5) Uani d 1 . .
    O O2 0.3413(3) 0.6659(3) 1.3551(2) 0.0223(4) Uani d 1 . .
    O O6 0.7705(4) 0.9702(4) 0.8108(3) 0.0346(6) Uani d 1 . .
    O O5 0.8755(3) 0.4606(3) 0.5889(2) 0.0230(4) Uani d 1 . .
    O O7 0.9441(4) 0.5415(4) 0.3428(3) 0.0338(5) Uani d 1 . .
    N N1 0.4571(3) 0.5128(3) 0.5815(2) 0.0161(4) Uani d 1 . .
    H H1A 0.5904 0.5072 0.5822 0.024 Uiso calc 1 . .
    H H1B 0.4329 0.5936 0.674 0.024 Uiso calc 1 . .
    H H1C 0.4195 0.5676 0.5112 0.024 Uiso calc 1 . .
    N N2 0.6159(3) 0.1137(3) 0.5979(2) 0.0162(4) Uani d 1 . .
    H H2A 0.7043 0.2233 0.5941 0.024 Uiso calc 1 . .
    H H2B 0.5935 0.0126 0.5057 0.024 Uiso calc 1 . .
    H H2C 0.6677 0.064 0.6671 0.024 Uiso calc 1 . .
    H H19 0.875(7) 0.639(7) 0.346(5) 0.050(13) Uiso d 1 . .
    H H18 1.071(6) 0.586(5) 0.333(4) 0.026(9) Uiso d 1 . .
    H H20 0.867(8) 0.900(8) 0.812(6) 0.057(14) Uiso d 1 . .
    H H17 0.903(8) 0.478(8) 0.507(7) 0.068(16) Uiso d 1 . .
    H H21 0.667(8) 0.937(8) 0.842(6) 0.057(15) Uiso d 1 . .
    H H16 0.951(6) 0.543(7) 0.664(5) 0.042(11) Uiso d 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
    C2 C6 . 1.387(4) ?
    C2 C3 . 1.393(3) ?
    C2 C1 . 1.514(3) ?
    C14 C13 . 1.393(4) ?
    C14 C15 . 1.389(4) ?
    C14 H14 . 0.95 ?
    C10 C15 . 1.394(4) ?
    C10 C11 . 1.401(4) ?
    C10 C9 . 1.521(3) ?
    C13 C12 . 1.394(3) ?
    C13 C16 . 1.514(3) ?
    C4 C7 . 1.394(4) ?
    C4 C3 . 1.395(3) ?
    C4 H4 . 0.95 ?
    C15 H15 . 0.95 ?
    C9 N2 . 1.501(4) ?
    C9 C8 . 1.549(3) ?
    C9 H9 . 1.0 ?
    C1 O4 . 1.256(3) ?
    C1 O3 . 1.252(4) ?
    C12 C11 . 1.394(4) ?
    C12 H12 . 0.95 ?
    C8 N1 . 1.507(3) ?
    C8 C7 . 1.516(3) ?
    C8 H8 . 1.0 ?
    C6 C5 . 1.393(4) ?
    C6 H6 . 0.95 ?
    C5 C7 . 1.396(3) ?
    C5 H5 . 0.95 ?
    C3 H3 . 0.95 ?
    C16 O1 . 1.255(3) ?
    C16 O2 . 1.262(3) ?
    C11 H11 . 0.95 ?
    O6 H20 . 0.88(6) ?
    O6 H21 . 0.81(6) ?
    O5 H17 . 0.85(6) ?
    O5 H16 . 0.83(5) ?
    O7 H19 . 0.87(5) ?
    O7 H18 . 0.89(4) ?
    N1 H1A . 0.91 ?
    N1 H1B . 0.91 ?
    N1 H1C . 0.91 ?
    N2 H2A . 0.91 ?
    N2 H2B . 0.91 ?
    N2 H2C . 0.91 ?
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
    C6 C2 C3 . . 119.0(2) ?
    C6 C2 C1 . . 120.1(2) ?
    C3 C2 C1 . . 120.9(2) ?
    C13 C14 C15 . . 120.9(2) ?
    C13 C14 H14 . . 119.5 ?
    C15 C14 H14 . . 119.5 ?
    C15 C10 C11 . . 118.5(2) ?
    C15 C10 C9 . . 122.3(2) ?
    C11 C10 C9 . . 119.1(2) ?
    C14 C13 C12 . . 119.0(2) ?
    C14 C13 C16 . . 118.8(2) ?
    C12 C13 C16 . . 122.1(2) ?
    C7 C4 C3 . . 120.0(2) ?
    C7 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C14 C15 C10 . . 120.6(2) ?
    C14 C15 H15 . . 119.7 ?
    C10 C15 H15 . . 119.7 ?
    N2 C9 C10 . . 110.8(2) ?
    N2 C9 C8 . . 112.81(19) ?
    C10 C9 C8 . . 111.31(19) ?
    N2 C9 H9 . . 107.2 ?
    C10 C9 H9 . . 107.2 ?
    C8 C9 H9 . . 107.2 ?
    O4 C1 O3 . . 124.7(2) ?
    O4 C1 C2 . . 117.4(2) ?
    O3 C1 C2 . . 117.9(2) ?
    C11 C12 C13 . . 120.1(2) ?
    C11 C12 H12 . . 119.9 ?
    C13 C12 H12 . . 119.9 ?
    N1 C8 C7 . . 110.9(2) ?
    N1 C8 C9 . . 111.91(18) ?
    C7 C8 C9 . . 114.34(19) ?
    N1 C8 H8 . . 106.4 ?
    C7 C8 H8 . . 106.4 ?
    C9 C8 H8 . . 106.4 ?
    C2 C6 C5 . . 120.8(2) ?
    C2 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C6 C5 C7 . . 120.1(2) ?
    C6 C5 H5 . . 120.0 ?
    C7 C5 H5 . . 120.0 ?
    C2 C3 C4 . . 120.7(2) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    O1 C16 O2 . . 122.6(2) ?
    O1 C16 C13 . . 118.3(2) ?
    O2 C16 C13 . . 119.1(2) ?
    C12 C11 C10 . . 120.9(2) ?
    C12 C11 H11 . . 119.5 ?
    C10 C11 H11 . . 119.5 ?
    C4 C7 C5 . . 119.4(2) ?
    C4 C7 C8 . . 122.0(2) ?
    C5 C7 C8 . . 118.6(2) ?
    H20 O6 H21 . . 118.(5) ?
    H17 O5 H16 . . 113.(4) ?
    H19 O7 H18 . . 109.(4) ?
    C8 N1 H1A . . 109.5 ?
    C8 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C8 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
    C9 N2 H2A . . 109.5 ?
    C9 N2 H2B . . 109.5 ?
    H2A N2 H2B . . 109.5 ?
    C9 N2 H2C . . 109.5 ?
    H2A N2 H2C . . 109.5 ?
    H2B N2 H2C . . 109.5 ?
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
    C15 C14 C13 C12 . . . . 0.1(4) ?
    C15 C14 C13 C16 . . . . 177.8(2) ?
    C13 C14 C15 C10 . . . . -0.2(4) ?
    C11 C10 C15 C14 . . . . 0.6(4) ?
    C9 C10 C15 C14 . . . . 178.5(2) ?
    C15 C10 C9 N2 . . . . 26.1(3) ?
    C11 C10 C9 N2 . . . . -155.9(2) ?
    C15 C10 C9 C8 . . . . -100.3(3) ?
    C11 C10 C9 C8 . . . . 77.7(3) ?
    C6 C2 C1 O4 . . . . 6.4(4) ?
    C3 C2 C1 O4 . . . . -174.5(2) ?
    C6 C2 C1 O3 . . . . -172.6(3) ?
    C3 C2 C1 O3 . . . . 6.6(4) ?
    C14 C13 C12 C11 . . . . -0.3(4) ?
    C16 C13 C12 C11 . . . . -177.9(2) ?
    N2 C9 C8 N1 . . . . -73.5(2) ?
    C10 C9 C8 N1 . . . . 51.7(3) ?
    N2 C9 C8 C7 . . . . 53.6(3) ?
    C10 C9 C8 C7 . . . . 178.8(2) ?
    C3 C2 C6 C5 . . . . -1.9(4) ?
    C1 C2 C6 C5 . . . . 177.3(2) ?
    C2 C6 C5 C7 . . . . 1.1(4) ?
    C6 C2 C3 C4 . . . . 0.5(4) ?
    C1 C2 C3 C4 . . . . -178.6(2) ?
    C7 C4 C3 C2 . . . . 1.7(4) ?
    C14 C13 C16 O1 . . . . 8.0(4) ?
    C12 C13 C16 O1 . . . . -174.4(2) ?
    C14 C13 C16 O2 . . . . -170.7(2) ?
    C12 C13 C16 O2 . . . . 7.0(4) ?
    C13 C12 C11 C10 . . . . 0.6(4) ?
    C15 C10 C11 C12 . . . . -0.8(4) ?
    C9 C10 C11 C12 . . . . -178.8(2) ?
    C3 C4 C7 C5 . . . . -2.5(4) ?
    C3 C4 C7 C8 . . . . 178.3(2) ?
    C6 C5 C7 C4 . . . . 1.2(4) ?
    C6 C5 C7 C8 . . . . -179.6(2) ?
    N1 C8 C7 C4 . . . . 47.4(3) ?
    C9 C8 C7 C4 . . . . -80.3(3) ?
    N1 C8 C7 C5 . . . . -131.8(2) ?
    C9 C8 C7 C5 . . . . 100.6(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
    N1 H1A O5 1_555 0.91 2.01 2.911(3) 173
    N1 H1B O3 1_566 0.91 1.80 2.686(3) 165
    N1 H1C O2 1_554 0.91 1.90 2.807(3) 176
    N2 H2A O5 1_555 0.91 1.89 2.798(3) 177
    N2 H2B O1 1_544 0.91 1.93 2.787(3) 156
    N2 H2C O6 1_545 0.91 1.83 2.744(4) 178
    O7 H19 O1 1_554 0.87(5) 1.92(5) 2.768(4) 162(5)
    O7 H18 O2 1_654 0.89(4) 1.81(4) 2.688(3) 166(4)
    O6 H20 O4 1_666 0.87(6) 1.85(6) 2.720(4) 172(5)
    O5 H17 O7 1_555 0.85(7) 1.77(7) 2.619(4) 172(6)
    O6 H21 O3 1_566 0.81(6) 1.93(5) 2.696(3) 157(5)
    O5 H16 O4 1_666 0.84(4) 1.83(4) 2.654(2) 166(4)
