#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/87/2218748.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_2218748
loop_
_publ_author_name
'Habib, Hesham A.'
'Janiak, Christoph'
_publ_section_title
;
 Benzene-1,3,5-tricarboxylic
 acid--1,2-bis(1,2,4-triazol-4-yl)ethane--water (4/1/2)
;
_journal_coeditor_code           KJ2089
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1199
_journal_paper_doi               10.1107/S1600536808015808
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '4C9 H6 O6 , C6 H8 N6 , 2H2 O'
_chemical_formula_moiety         '4C9 H6 O6 , C6 H8 N6 , 2H2 O'
_chemical_formula_sum            'C21 H18 N3 O13'
_chemical_formula_weight         1040.76
_chemical_name_systematic
;
benzene-1,3,5-tricarboxylic acid--1,2-bis(1,2,4-triazol-4-yl)ethane--water
(4/1/2)
;
_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           SHELXL97
_cell_angle_alpha                108.8010(10)
_cell_angle_beta                 98.7370(10)
_cell_angle_gamma                113.3400(10)
_cell_formula_units_Z            1
_cell_length_a                   9.79890(10)
_cell_length_b                   10.7511(2)
_cell_length_c                   12.6578(2)
_cell_measurement_reflns_used    5028
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.23
_cell_volume                     1097.44(3)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20984
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0412
_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)+(0.0562P)²+0.0985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                3452
_reflns_number_total             4824
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2089.cif
_cod_data_source_block           I
_cod_database_code               2218748
_cod_database_fobs_code          2218748
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 O1 1.35077(13) 0.71622(12) 0.20868(9) 0.0281(3) Uani d . 1
O O2 1.12433(15) 0.50380(13) 0.11195(10) 0.0342(3) Uani d . 1
H H2 1.169(2) 0.490(2) 0.0526(19) 0.051 Uiso d . 1
O O3 0.72628(14) 0.32810(13) 0.28747(10) 0.0357(3) Uani d . 1
O O4 0.75183(14) 0.47603(13) 0.46864(10) 0.0295(3) Uani d . 1
H H4 0.658(3) 0.402(2) 0.4509(17) 0.044 Uiso d . 1
O O5 1.23563(17) 0.97506(14) 0.69889(11) 0.0479(4) Uani d . 1
O O6 1.41605(14) 1.03213(13) 0.61107(11) 0.0335(3) Uani d . 1
H H6 1.473(3) 1.117(2) 0.6791(19) 0.050 Uiso d . 1
C C1 1.15857(19) 0.65177(17) 0.30595(13) 0.0226(3) Uani d . 1
C C2 1.01588(19) 0.54260(17) 0.29865(13) 0.0241(4) Uani d . 1
H H2A 0.9603 0.4520 0.2306 0.031(5) Uiso calc R 1
C C3 0.95434(19) 0.56593(17) 0.39110(13) 0.0224(3) Uani d . 1
C C4 1.03774(18) 0.69911(17) 0.49313(13) 0.0230(3) Uani d . 1
H H4A 0.9963 0.7159 0.5555 0.028 Uiso calc R 1
C C5 1.18299(19) 0.80705(17) 0.50200(13) 0.0228(3) Uani d . 1
C C6 1.24244(19) 0.78375(17) 0.40836(13) 0.0230(3) Uani d . 1
H H6A 1.3397 0.8576 0.4144 0.028 Uiso calc R 1
C C7 1.22269(19) 0.62928(17) 0.20573(13) 0.0235(3) Uani d . 1
C C8 0.79976(19) 0.44429(17) 0.37606(14) 0.0237(3) Uani d . 1
C C9 1.2777(2) 0.94488(18) 0.61364(14) 0.0260(4) Uani d . 1
O O7 0.23309(14) 0.11931(13) 0.42638(10) 0.0327(3) Uani d . 1
H H7 0.230(2) 0.064(2) 0.349(2) 0.049 Uiso d . 1
O O8 0.47138(14) 0.26410(13) 0.43007(10) 0.0369(3) Uani d . 1
O O9 0.82100(16) 0.72343(14) 0.77430(11) 0.0405(3) Uani d . 1
H H9 0.916(3) 0.808(3) 0.814(2) 0.061 Uiso d . 1
O O10 0.75891(16) 0.79239(14) 0.93837(11) 0.0487(4) Uani d . 1
O O11 0.23548(16) 0.46243(14) 0.93776(11) 0.0443(4) Uani d . 1
O O12 0.10133(15) 0.22723(13) 0.79990(11) 0.0360(3) Uani d . 1
H H12 0.029(3) 0.214(2) 0.8372(19) 0.054 Uiso d . 1
C C11 0.40237(18) 0.33372(17) 0.60392(13) 0.0226(3) Uani d . 1
C C12 0.54215(19) 0.46733(17) 0.66014(14) 0.0248(4) Uani d . 1
H H12A 0.6137 0.4932 0.6193 0.030 Uiso calc R 1
C C13 0.57695(19) 0.56305(17) 0.77641(14) 0.0252(4) Uani d . 1
C C14 0.47026(19) 0.52582(17) 0.83609(14) 0.0259(4) Uani d . 1
H H14A 0.4929 0.5908 0.9144 0.031 Uiso calc R 1
C C15 0.33011(19) 0.39277(17) 0.78027(14) 0.0242(4) Uani d . 1
C C16 0.29563(19) 0.29562(17) 0.66414(13) 0.0226(3) Uani d . 1
H H16A 0.2012 0.2052 0.6267 0.027 Uiso calc R 1
C C17 0.37241(19) 0.23634(17) 0.47946(14) 0.0255(4) Uani d . 1
C C18 0.7287(2) 0.70561(18) 0.83851(15) 0.0295(4) Uani d . 1
C C19 0.2168(2) 0.36255(19) 0.84716(14) 0.0276(4) Uani d . 1
O O13 1.09496(16) 0.94370(15) 0.86765(12) 0.0442(4) Uani d . 1
H H13A 1.134(3) 1.031(3) 0.932(2) 0.066 Uiso d . 1
H H13B 1.129(3) 0.959(3) 0.813(2) 0.066 Uiso d . 1
C C21 0.2033(2) -0.17823(19) 0.03864(14) 0.0307(4) Uani d . 1
H H21A 0.1519 -0.2613 -0.0349 0.037 Uiso calc R 1
C C22 0.3793(2) 0.02501(18) 0.18472(14) 0.0277(4) Uani d . 1
H H22A 0.4747 0.1115 0.2332 0.033 Uiso calc R 1
C C23 0.4714(2) -0.0680(2) 0.01332(16) 0.0338(4) Uani d . 1
H H23A 0.4241 -0.1585 -0.0605 0.041 Uiso calc R 1
H H23B 0.5608 -0.0657 0.0623 0.041 Uiso calc R 1
N N1 0.25099(16) -0.01876(15) 0.21283(12) 0.0281(3) Uani d . 1
N N2 0.13810(16) -0.14927(15) 0.11899(12) 0.0293(3) Uani d . 1
N N3 0.35506(16) -0.07258(15) 0.07521(11) 0.0272(3) 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 O2 H2 . . 110.6(13)
C8 O4 H4 . . 107.2(13)
C9 O6 H6 . . 112.6(13)
C2 C1 C6 . . 119.32(14)
C2 C1 C7 . . 120.95(14)
C6 C1 C7 . . 119.73(14)
C1 C2 C3 . . 120.72(14)
C1 C2 H2A . . 119.6
C3 C2 H2A . . 119.6
C2 C3 C4 . . 119.85(14)
C2 C3 C8 . . 117.56(14)
C4 C3 C8 . . 122.59(14)
C5 C4 C3 . . 119.53(14)
C5 C4 H4A . . 120.2
C3 C4 H4A . . 120.2
C6 C5 C4 . . 120.21(14)
C6 C5 C9 . . 119.87(14)
C4 C5 C9 . . 119.88(13)
C1 C6 C5 . . 120.34(14)
C1 C6 H6A . . 119.8
C5 C6 H6A . . 119.8
O1 C7 O2 . . 123.19(14)
O1 C7 C1 . . 124.36(15)
O2 C7 C1 . . 112.45(13)
O3 C8 O4 . . 123.84(15)
O3 C8 C3 . . 123.02(14)
O4 C8 C3 . . 113.14(14)
O5 C9 O6 . . 122.58(16)
O5 C9 C5 . . 124.55(15)
O6 C9 C5 . . 112.86(13)
C17 O7 H7 . . 107.8(13)
C18 O9 H9 . . 112.4(14)
C19 O12 H12 . . 113.6(14)
C12 C11 C16 . . 119.86(14)
C12 C11 C17 . . 117.73(14)
C16 C11 C17 . . 122.41(14)
C11 C12 C13 . . 120.45(14)
C11 C12 H12A . . 119.8
C13 C12 H12A . . 119.8
C14 C13 C12 . . 119.73(15)
C14 C13 C18 . . 119.44(14)
C12 C13 C18 . . 120.83(14)
C13 C14 C15 . . 120.10(15)
C13 C14 H14A . . 120.0
C15 C14 H14A . . 120.0
C14 C15 C16 . . 120.34(14)
C14 C15 C19 . . 117.53(14)
C16 C15 C19 . . 122.06(15)
C15 C16 C11 . . 119.51(15)
C15 C16 H16A . . 120.2
C11 C16 H16A . . 120.2
O8 C17 O7 . . 122.24(14)
O8 C17 C11 . . 122.17(15)
O7 C17 C11 . . 115.59(13)
O10 C18 O9 . . 125.16(16)
O10 C18 C13 . . 121.74(15)
O9 C18 C13 . . 113.10(14)
O11 C19 O12 . . 125.08(15)
O11 C19 C15 . . 120.02(15)
O12 C19 C15 . . 114.90(14)
H13A O13 H13B . . 110(2)
N2 C21 N3 . . 110.82(14)
N2 C21 H21A . . 124.6
N3 C21 H21A . . 124.6
N1 C22 N3 . . 110.10(15)
N1 C22 H22A . . 124.9
N3 C22 H22A . . 124.9
N3 C23 C23 . 2_655 111.15(18)
N3 C23 H23A . . 109.4
C23 C23 H23A 2_655 . 109.4
N3 C23 H23B . . 109.4
C23 C23 H23B 2_655 . 109.4
H23A C23 H23B . . 108.0
C22 N1 N2 . . 107.37(13)
C21 N2 N1 . . 106.94(13)
C21 N3 C22 . . 104.77(13)
C21 N3 C23 . . 127.89(14)
C22 N3 C23 . . 127.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.2182(19)
O2 C7 . 1.3221(19)
O2 H2 . 0.92(2)
O3 C8 . 1.2147(19)
O4 C8 . 1.3217(19)
O4 H4 . 0.88(2)
O5 C9 . 1.2065(19)
O6 C9 . 1.3204(19)
O6 H6 . 0.91(2)
C1 C2 . 1.390(2)
C1 C6 . 1.391(2)
C1 C7 . 1.492(2)
C2 C3 . 1.393(2)
C2 H2A . 0.9400
C3 C4 . 1.395(2)
C3 C8 . 1.491(2)
C4 C5 . 1.394(2)
C4 H4A . 0.9400
C5 C6 . 1.393(2)
C5 C9 . 1.489(2)
C6 H6A . 0.9400
O7 C17 . 1.3090(19)
O7 H7 . 0.96(2)
O8 C17 . 1.2230(18)
O9 C18 . 1.304(2)
O9 H9 . 0.91(3)
O10 C18 . 1.210(2)
O11 C19 . 1.2201(19)
O12 C19 . 1.298(2)
O12 H12 . 0.90(2)
C11 C12 . 1.390(2)
C11 C16 . 1.395(2)
C11 C17 . 1.489(2)
C12 C13 . 1.391(2)
C12 H12A . 0.9400
C13 C14 . 1.388(2)
C13 C18 . 1.497(2)
C14 C15 . 1.389(2)
C14 H14A . 0.9400
C15 C16 . 1.395(2)
C15 C19 . 1.494(2)
C16 H16A . 0.9400
O13 H13A . 0.91(2)
O13 H13B . 0.85(3)
C21 N2 . 1.300(2)
C21 N3 . 1.353(2)
C21 H21A . 0.9400
C22 N1 . 1.306(2)
C22 N3 . 1.358(2)
C22 H22A . 0.9400
C23 N3 . 1.472(2)
C23 C23 2_655 1.513(3)
C23 H23A . 0.9800
C23 H23B . 0.9800
N1 N2 . 1.3784(18)
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 O11 1_654 0.92(2) 1.67(2) 2.594(2) 175(2)
O4 H4 O8 . 0.88(2) 1.75(2) 2.626(2) 174(2)
O6 H6 O1 2_876 0.91(2) 1.84(2) 2.699(2) 157(2)
O7 H7 N1 . 0.96(2) 1.75(2) 2.703(2) 172(2)
O9 H9 O13 . 0.91(3) 1.63(3) 2.531(2) 170(2)
O12 H12 N2 2_556 0.90(2) 1.76(2) 2.644(2) 167(2)
O13 H13A O10 2_777 0.91(2) 1.81(3) 2.711(2) 171(2)
O13 H13B O5 . 0.85(3) 1.92(3) 2.751(2) 167(2)
