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#$Date: 2023-05-04 11:21:34 +0300 (Thu, 04 May 2023) $
#$Revision: 282986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107127.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107127
loop_
_publ_author_name
'Sheng, Liang-Quan'
'Xu, Hua-Jie'
_publ_section_title
;
 Crystal structure of 5-(4-(1H-tetrazol-5-yl)phenyl)-1H-imidazol-3-ium
 7-carboxy-1,3-dioxo-1H,3H-benzo[de]isochromene-6-carboxylate monohydrate
 4,5-anhydride, C24H16N6O8
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1149
_journal_page_last               1151
_journal_paper_doi               10.1515/ncrs-2016-0095
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C24 H16 N6 O8'
_chemical_formula_weight         516.43
_chemical_name_systematic
; 
5-(4-(1H-tetrazol-5-yl)phenyl)-1H-
imidazol-3-ium 7-carboxy-1,3-dioxo-1H,3H-benzo[de]
isochromene-6-carboxylate monohydrate 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 112.888(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9705(10)
_cell_length_b                   25.494(3)
_cell_length_c                   10.2372(12)
_cell_measurement_reflns_used    116
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.45
_cell_measurement_theta_min      2.67
_cell_volume                     2156.9(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart Apex CCD '
_diffrn_measurement_method       'phi and omega scans'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15349
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0467
_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)+(0.0595P)²+0.3968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                3727
_reflns_number_total             5365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0095_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        2156.8(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107127
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9775(2) 0.15983(7) 0.2801(2) 0.0418(5) Uani 1 1 d . . .
H1 H 1.0570 0.1361 0.2821 0.050 Uiso 1 1 calc R . .
C2 C 0.8689(2) 0.14650(7) 0.3411(2) 0.0394(4) Uani 1 1 d . . .
H2 H 0.8772 0.1141 0.3851 0.047 Uiso 1 1 calc R . .
C3 C 0.7479(2) 0.18123(7) 0.3366(2) 0.0374(4) Uani 1 1 d . . .
C4 C 0.7401(3) 0.22992(8) 0.2734(3) 0.0579(6) Uani 1 1 d . . .
H4 H 0.6599 0.2536 0.2704 0.070 Uiso 1 1 calc R . .
C5 C 0.8491(3) 0.24358(8) 0.2153(3) 0.0566(6) Uani 1 1 d . . .
H5 H 0.8434 0.2766 0.1748 0.068 Uiso 1 1 calc R . .
C6 C 0.9682(2) 0.20826(7) 0.2166(2) 0.0405(4) Uani 1 1 d . . .
C7 C 1.0816(2) 0.22242(7) 0.1513(2) 0.0412(4) Uani 1 1 d . . .
C8 C 0.6309(2) 0.16930(7) 0.3999(2) 0.0368(4) Uani 1 1 d . . .
C9 C 0.5171(2) 0.20060(8) 0.4160(2) 0.0451(5) Uani 1 1 d . . .
H9 H 0.4950 0.2352 0.3861 0.054 Uiso 1 1 calc R . .
C10 C 0.5037(3) 0.12486(8) 0.5098(2) 0.0462(5) Uani 1 1 d . . .
H10 H 0.4721 0.0979 0.5547 0.055 Uiso 1 1 calc R . .
C11 C 0.8313(2) 0.09323(7) -0.0673(2) 0.0357(4) Uani 1 1 d . . .
C12 C 0.8035(2) 0.06284(6) 0.04371(18) 0.0299(4) Uani 1 1 d . . .
C13 C 0.65633(19) 0.06859(6) 0.06306(17) 0.0272(3) Uani 1 1 d . . .
C14 C 0.5385(2) 0.10438(6) -0.02162(18) 0.0315(4) Uani 1 1 d . . .
C15 C 0.5733(2) 0.13782(7) -0.1231(2) 0.0367(4) Uani 1 1 d . . .
C17 C 0.9214(2) 0.03010(7) 0.12865(19) 0.0341(4) Uani 1 1 d . . .
H17 H 1.0153 0.0251 0.1122 0.041 Uiso 1 1 calc R . .
C18 C 0.9010(2) 0.00396(7) 0.24069(19) 0.0340(4) Uani 1 1 d . . .
H18 H 0.9842 -0.0171 0.3004 0.041 Uiso 1 1 calc R . .
C19 C 0.7610(2) 0.00868(6) 0.26482(18) 0.0294(4) Uani 1 1 d . . .
C20 C 0.62954(19) 0.03924(6) 0.17086(17) 0.0263(3) Uani 1 1 d . . .
C21 C 0.47420(19) 0.04475(6) 0.17915(18) 0.0292(4) Uani 1 1 d . . .
C22 C 0.3635(2) 0.07996(7) 0.0946(2) 0.0365(4) Uani 1 1 d . . .
H22 H 0.2649 0.0837 0.1038 0.044 Uiso 1 1 calc R . .
C23 C 0.3951(2) 0.11045(7) -0.0055(2) 0.0376(4) Uani 1 1 d . . .
H23 H 0.3192 0.1347 -0.0606 0.045 Uiso 1 1 calc R . .
C24 C 0.4196(2) 0.00940(7) 0.26943(19) 0.0326(4) Uani 1 1 d . . .
C25 C 0.7664(2) -0.01363(7) 0.40364(19) 0.0337(4) Uani 1 1 d . . .
N1 N 0.6202(2) 0.12192(6) 0.46113(18) 0.0407(4) Uani 1 1 d . . .
N2 N 0.4403(2) 0.17174(7) 0.4847(2) 0.0482(4) Uani 1 1 d . . .
N3 N 1.1208(2) 0.27091(7) 0.12953(19) 0.0436(4) Uani 1 1 d . . .
N4 N 1.2454(3) 0.21945(7) 0.0464(2) 0.0641(6) Uani 1 1 d . . .
N5 N 1.1583(2) 0.18932(7) 0.1001(2) 0.0621(6) Uani 1 1 d . . .
N6 N 1.2228(2) 0.26830(7) 0.0636(2) 0.0503(4) Uani 1 1 d . . .
O1 O 0.44522(17) -0.03725(5) 0.27658(15) 0.0430(3) Uani 1 1 d . . .
O2 O 0.33379(16) 0.03381(5) 0.32937(15) 0.0447(3) Uani 1 1 d D . .
O3 O 0.81588(19) -0.05878(5) 0.43785(16) 0.0516(4) Uani 1 1 d . . .
O4 O 0.72694(15) 0.01845(5) 0.48173(13) 0.0363(3) Uani 1 1 d . . .
O5 O 0.48534(19) 0.17133(6) -0.19473(16) 0.0547(4) Uani 1 1 d . . .
O6 O 0.72044(16) 0.13194(5) -0.13537(15) 0.0431(3) Uani 1 1 d . . .
O7 O 0.94400(17) 0.08775(6) -0.10082(16) 0.0518(4) Uani 1 1 d . . .
O8 O 0.0431(2) 0.36853(6) 0.1834(2) 0.0587(5) Uani 1 1 d . . .
H7 H 0.675(3) 0.0905(9) 0.469(2) 0.059(7) Uiso 1 1 d . . .
H3 H 1.097(3) 0.3038(10) 0.153(3) 0.064(7) Uiso 1 1 d . . .
H8 H 0.352(3) 0.1853(10) 0.507(3) 0.083(8) Uiso 1 1 d . . .
H12 H 0.100(4) 0.3920(13) 0.150(4) 0.111(11) Uiso 1 1 d . . .
H13 H 0.017(3) 0.3791(11) 0.250(3) 0.084(9) Uiso 1 1 d . . .
H11 H 0.313(3) 0.0106(9) 0.391(3) 0.094(10) Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 120.36(17) . .
C6 C1 H1 119.8 . .
C2 C1 H1 119.8 . .
C3 C2 C1 120.39(17) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C2 C3 C4 118.84(17) . .
C2 C3 C8 122.64(16) . .
C4 C3 C8 118.50(16) . .
C5 C4 C3 120.90(18) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 120.30(19) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C1 C6 C5 119.18(17) . .
C1 C6 C7 120.64(17) . .
C5 C6 C7 120.17(17) . .
N5 C7 N3 108.41(17) . .
N5 C7 C6 125.90(17) . .
N3 C7 C6 125.67(17) . .
C9 C8 N1 105.74(16) . .
C9 C8 C3 129.43(17) . .
N1 C8 C3 124.80(16) . .
C8 C9 N2 107.35(17) . .
C8 C9 H9 126.3 . .
N2 C9 H9 126.3 . .
N2 C10 N1 108.98(17) . .
N2 C10 H10 125.5 . .
N1 C10 H10 125.5 . .
O7 C11 O6 117.47(16) . .
O7 C11 C12 125.11(17) . .
O6 C11 C12 117.40(14) . .
C17 C12 C13 120.54(15) . .
C17 C12 C11 119.50(15) . .
C13 C12 C11 119.95(15) . .
C14 C13 C12 119.84(14) . .
C14 C13 C20 120.17(14) . .
C12 C13 C20 119.97(15) . .
C23 C14 C13 120.94(15) . .
C23 C14 C15 119.26(16) . .
C13 C14 C15 119.70(15) . .
O5 C15 O6 116.53(16) . .
O5 C15 C14 125.09(17) . .
O6 C15 C14 118.35(15) . .
C12 C17 C18 119.95(15) . .
C12 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
C19 C18 C17 121.65(16) . .
C19 C18 H18 119.2 . .
C17 C18 H18 119.2 . .
C18 C19 C20 119.93(15) . .
C18 C19 C25 115.93(15) . .
C20 C19 C25 123.62(14) . .
C19 C20 C13 117.57(14) . .
C19 C20 C21 125.44(14) . .
C13 C20 C21 116.94(14) . .
C22 C21 C20 120.59(14) . .
C22 C21 C24 116.92(14) . .
C20 C21 C24 122.26(14) . .
C21 C22 C23 121.58(15) . .
C21 C22 H22 119.2 . .
C23 C22 H22 119.2 . .
C14 C23 C22 119.55(16) . .
C14 C23 H23 120.2 . .
C22 C23 H23 120.2 . .
O1 C24 O2 124.81(16) . .
O1 C24 C21 121.84(15) . .
O2 C24 C21 113.19(14) . .
O3 C25 O4 124.90(16) . .
O3 C25 C19 119.57(15) . .
O4 C25 C19 115.38(14) . .
C10 N1 C8 109.01(16) . .
C10 N1 H7 118.8(13) . .
C8 N1 H7 132.1(14) . .
C10 N2 C9 108.92(17) . .
C10 N2 H8 127.7(15) . .
C9 N2 H8 123.4(15) . .
C7 N3 N6 108.50(16) . .
C7 N3 H3 134.5(14) . .
N6 N3 H3 116.9(14) . .
N6 N4 N5 110.29(16) . .
C7 N5 N4 105.71(16) . .
N4 N6 N3 107.10(16) . .
C24 O2 H11 108.7(17) . .
C15 O6 C11 123.85(13) . .
H12 O8 H13 117(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.383(3) .
C1 C2 1.388(3) .
C1 H1 0.9300 .
C2 C3 1.388(3) .
C2 H2 0.9300 .
C3 C4 1.389(3) .
C3 C8 1.464(2) .
C4 C5 1.373(3) .
C4 H4 0.9300 .
C5 C6 1.393(3) .
C5 H5 0.9300 .
C6 C7 1.463(2) .
C7 N5 1.319(2) .
C7 N3 1.328(2) .
C8 C9 1.356(3) .
C8 N1 1.381(2) .
C9 N2 1.374(2) .
C9 H9 0.9300 .
C10 N2 1.305(3) .
C10 N1 1.324(2) .
C10 H10 0.9300 .
C11 O7 1.196(2) .
C11 O6 1.382(2) .
C11 C12 1.474(2) .
C12 C17 1.362(2) .
C12 C13 1.417(2) .
C13 C14 1.410(2) .
C13 C20 1.429(2) .
C14 C23 1.368(2) .
C14 C15 1.469(2) .
C15 O5 1.200(2) .
C15 O6 1.381(2) .
C17 C18 1.398(2) .
C17 H17 0.9300 .
C18 C19 1.376(2) .
C18 H18 0.9300 .
C19 C20 1.428(2) .
C19 C25 1.514(2) .
C20 C21 1.436(2) .
C21 C22 1.368(2) .
C21 C24 1.503(2) .
C22 C23 1.399(2) .
C22 H22 0.9300 .
C23 H23 0.9300 .
C24 O1 1.208(2) .
C24 O2 1.313(2) .
C25 O3 1.234(2) .
C25 O4 1.286(2) .
N1 H7 0.92(2) .
N2 H8 0.97(3) .
N3 N6 1.333(2) .
N3 H3 0.92(2) .
N4 N6 1.285(2) .
N4 N5 1.356(2) .
O2 H11 0.933(17) .
O8 H12 0.93(3) .
O8 H13 0.85(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 1.2(3) . . . .
C1 C2 C3 C4 -1.6(3) . . . .
C1 C2 C3 C8 -179.61(18) . . . .
C2 C3 C4 C5 0.4(4) . . . .
C8 C3 C4 C5 178.5(2) . . . .
C3 C4 C5 C6 1.1(4) . . . .
C2 C1 C6 C5 0.3(3) . . . .
C2 C1 C6 C7 -179.54(18) . . . .
C4 C5 C6 C1 -1.5(4) . . . .
C4 C5 C6 C7 178.4(2) . . . .
C1 C6 C7 N5 25.6(3) . . . .
C5 C6 C7 N5 -154.3(2) . . . .
C1 C6 C7 N3 -156.6(2) . . . .
C5 C6 C7 N3 23.5(3) . . . .
C2 C3 C8 C9 173.0(2) . . . .
C4 C3 C8 C9 -5.0(3) . . . .
C2 C3 C8 N1 -4.7(3) . . . .
C4 C3 C8 N1 177.3(2) . . . .
N1 C8 C9 N2 -0.4(2) . . . .
C3 C8 C9 N2 -178.48(19) . . . .
O7 C11 C12 C17 8.5(3) . . . .
O6 C11 C12 C17 -169.85(16) . . . .
O7 C11 C12 C13 -172.74(18) . . . .
O6 C11 C12 C13 9.0(2) . . . .
C17 C12 C13 C14 177.19(16) . . . .
C11 C12 C13 C14 -1.6(2) . . . .
C17 C12 C13 C20 -1.1(2) . . . .
C11 C12 C13 C20 -179.84(15) . . . .
C12 C13 C14 C23 179.66(17) . . . .
C20 C13 C14 C23 -2.1(3) . . . .
C12 C13 C14 C15 -3.8(2) . . . .
C20 C13 C14 C15 174.43(15) . . . .
C23 C14 C15 O5 0.6(3) . . . .
C13 C14 C15 O5 -175.96(18) . . . .
C23 C14 C15 O6 178.46(16) . . . .
C13 C14 C15 O6 1.9(3) . . . .
C13 C12 C17 C18 -3.4(3) . . . .
C11 C12 C17 C18 175.43(16) . . . .
C12 C17 C18 C19 2.7(3) . . . .
C17 C18 C19 C20 2.5(3) . . . .
C17 C18 C19 C25 -169.49(16) . . . .
C18 C19 C20 C13 -6.7(2) . . . .
C25 C19 C20 C13 164.65(15) . . . .
C18 C19 C20 C21 176.09(16) . . . .
C25 C19 C20 C21 -12.6(3) . . . .
C14 C13 C20 C19 -172.24(15) . . . .
C12 C13 C20 C19 6.0(2) . . . .
C14 C13 C20 C21 5.2(2) . . . .
C12 C13 C20 C21 -176.54(15) . . . .
C19 C20 C21 C22 172.02(17) . . . .
C13 C20 C21 C22 -5.2(2) . . . .
C19 C20 C21 C24 -13.7(3) . . . .
C13 C20 C21 C24 169.03(15) . . . .
C20 C21 C22 C23 2.1(3) . . . .
C24 C21 C22 C23 -172.49(16) . . . .
C13 C14 C23 C22 -1.3(3) . . . .
C15 C14 C23 C22 -177.82(17) . . . .
C21 C22 C23 C14 1.3(3) . . . .
C22 C21 C24 O1 133.30(19) . . . .
C20 C21 C24 O1 -41.2(3) . . . .
C22 C21 C24 O2 -42.3(2) . . . .
C20 C21 C24 O2 143.25(16) . . . .
C18 C19 C25 O3 -50.4(2) . . . .
C20 C19 C25 O3 137.96(18) . . . .
C18 C19 C25 O4 125.43(17) . . . .
C20 C19 C25 O4 -46.2(2) . . . .
N2 C10 N1 C8 -0.8(2) . . . .
C9 C8 N1 C10 0.7(2) . . . .
C3 C8 N1 C10 178.89(19) . . . .
N1 C10 N2 C9 0.5(3) . . . .
C8 C9 N2 C10 0.0(3) . . . .
N5 C7 N3 N6 0.2(2) . . . .
C6 C7 N3 N6 -177.9(2) . . . .
N3 C7 N5 N4 -0.1(3) . . . .
C6 C7 N5 N4 178.1(2) . . . .
N6 N4 N5 C7 -0.1(3) . . . .
N5 N4 N6 N3 0.2(3) . . . .
C7 N3 N6 N4 -0.3(2) . . . .
O5 C15 O6 C11 -175.87(17) . . . .
C14 C15 O6 C11 6.1(3) . . . .
O7 C11 O6 C15 170.18(17) . . . .
C12 C11 O6 C15 -11.4(3) . . . .
