#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226958.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_2226958
loop_
_publ_author_name
'Lin, Jin Rui'
_publ_section_title
;
 Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid)
 monohydrate
;
_journal_coeditor_code           JH2161
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1967
_journal_paper_doi               10.1107/S1600536810026243
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C10 H9 N3 O2, H2 O'
_chemical_formula_moiety         '2(C10 H9 N3 O2), H2 O'
_chemical_formula_sum            'C20 H20 N6 O5'
_chemical_formula_weight         424.42
_chemical_name_systematic
;
Bis(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid) monohydrate
;
_space_group_IT_number           14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7419(13)
_cell_length_b                   15.842(3)
_cell_length_c                   19.643(4)
_cell_measurement_reflns_used    8429
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6600
_cell_measurement_theta_min      3.0650
_cell_volume                     2067.2(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20838
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0522
_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)+(0.1083P)²+0.6293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                3206
_reflns_number_total             4733
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2161.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226958
_cod_database_fobs_code          2226958
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_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
O O4 -0.2245(3) 0.25435(10) 1.04831(9) 0.0616(5) Uani d . 1 . .
H H4 -0.3031 0.2478 1.0754 0.092 Uiso calc R 1 . .
N N1 0.3101(2) 0.21148(10) 0.20357(8) 0.0427(4) Uani d . 1 . .
O O1 0.2105(2) 0.44007(10) 0.09705(9) 0.0604(5) Uani d . 1 . .
H H1 0.2133 0.4802 0.0709 0.091 Uiso calc R 1 . .
O O2 0.4704(3) 0.39675(10) 0.05055(9) 0.0658(5) Uani d . 1 . .
N N3 0.4944(3) 0.25050(10) 0.13134(10) 0.0505(5) Uani d . 1 . .
O O3 -0.1197(3) 0.12701(11) 1.08533(9) 0.0725(5) Uani d . 1 . .
N N6 0.0253(3) 0.25962(11) 0.95482(10) 0.0515(5) Uani d . 1 . .
N N4 0.2420(2) 0.17006(10) 0.93228(9) 0.0426(4) Uani d . 1 . .
C C17 0.1698(3) 0.13594(13) 0.98605(10) 0.0416(5) Uani d . 1 . .
N N5 0.1530(3) 0.24561(11) 0.91340(10) 0.0542(5) Uani d . 1 . .
C C16 0.3809(3) 0.13618(13) 0.89167(10) 0.0427(5) Uani d . 1 . .
C C7 0.2327(3) 0.28716(12) 0.18016(10) 0.0387(4) Uani d . 1 . .
C C9 0.3516(3) 0.38637(12) 0.08889(11) 0.0438(5) Uani d . 1 . .
C C8 0.3532(3) 0.31110(12) 0.13320(10) 0.0407(4) Uani d . 1 . .
C C6 0.2526(3) 0.15587(12) 0.25486(10) 0.0406(4) Uani d . 1 . .
C C18 0.0303(3) 0.19342(12) 0.99957(10) 0.0397(4) Uani d . 1 . .
C C19 -0.1097(3) 0.18755(13) 1.04937(10) 0.0435(5) Uani d . 1 . .
N N2 0.4702(3) 0.18997(11) 0.17417(10) 0.0544(5) Uani d . 1 . .
C C4 0.0066(4) 0.07727(15) 0.30104(13) 0.0555(6) Uani d . 1 . .
H H4A -0.1262 0.0602 0.2992 0.067 Uiso calc R 1 . .
C C3 0.1503(4) 0.04942(14) 0.35351(12) 0.0539(6) Uani d . 1 . .
H H3 0.1157 0.0135 0.3871 0.065 Uiso calc R 1 . .
C C1 0.3999(3) 0.12818(13) 0.30735(11) 0.0468(5) Uani d . 1 . .
H H1A 0.5329 0.1452 0.3096 0.056 Uiso calc R 1 . .
C C11 0.5459(3) 0.18340(15) 0.88273(12) 0.0535(5) Uani d . 1 . .
H H11 0.5721 0.2350 0.9051 0.064 Uiso calc R 1 . .
C C5 0.0549(3) 0.13048(14) 0.25048(11) 0.0495(5) Uani d . 1 . .
H H5 -0.0435 0.1487 0.2144 0.059 Uiso calc R 1 . .
C C10 0.0630(3) 0.32936(14) 0.20576(12) 0.0515(5) Uani d . 1 . .
H H10A -0.0615 0.3140 0.1770 0.077 Uiso calc R 1 . .
H H10B 0.0802 0.3895 0.2044 0.077 Uiso calc R 1 . .
H H10C 0.0606 0.3119 0.2524 0.077 Uiso calc R 1 . .
C C15 0.3431(4) 0.05856(14) 0.86021(12) 0.0542(6) Uani d . 1 . .
H H15 0.2322 0.0268 0.8671 0.065 Uiso calc R 1 . .
C C2 0.3460(4) 0.07454(14) 0.35661(12) 0.0528(5) Uani d . 1 . .
H H2 0.4441 0.0552 0.3924 0.063 Uiso calc R 1 . .
C C13 0.6347(4) 0.0763(2) 0.80763(13) 0.0709(8) Uani d . 1 . .
H H13 0.7194 0.0565 0.7784 0.085 Uiso calc R 1 . .
C C20 0.2496(4) 0.05710(17) 1.02157(13) 0.0694(8) Uani d . 1 . .
H H20A 0.2171 0.0100 0.9909 0.104 Uiso calc R 1 . .
H H20B 0.1901 0.0490 1.0621 0.104 Uiso calc R 1 . .
H H20C 0.3931 0.0614 1.0346 0.104 Uiso calc R 1 . .
C C12 0.6716(4) 0.1527(2) 0.83991(14) 0.0705(7) Uani d . 1 . .
H H12 0.7827 0.1843 0.8329 0.085 Uiso calc R 1 . .
C C14 0.4724(4) 0.02880(17) 0.81842(12) 0.0644(7) Uani d . 1 . .
H H14 0.4496 -0.0237 0.7974 0.077 Uiso calc R 1 . .
O O5 0.2055(3) 0.58080(13) 0.02879(12) 0.0749(6) Uani d . 1 . .
H H5A 0.290(5) 0.591(2) 0.0025(18) 0.098(11) Uiso d . 1 . .
H H5B 0.131(6) 0.622(3) 0.0310(19) 0.111(13) Uiso 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
_geom_angle_publ_flag
C19 O4 H4 . . 109.5 ?
N2 N1 C7 . . 111.55(15) ?
N2 N1 C6 . . 118.32(15) ?
C7 N1 C6 . . 130.07(16) ?
C9 O1 H1 . . 109.5 ?
N2 N3 C8 . . 109.73(16) ?
N5 N6 C18 . . 109.01(16) ?
C17 N4 N5 . . 111.38(15) ?
C17 N4 C16 . . 129.99(17) ?
N5 N4 C16 . . 118.46(16) ?
N4 C17 C18 . . 103.72(17) ?
N4 C17 C20 . . 123.68(18) ?
C18 C17 C20 . . 132.41(19) ?
N6 N5 N4 . . 106.70(16) ?
C11 C16 C15 . . 121.2(2) ?
C11 C16 N4 . . 119.10(19) ?
C15 C16 N4 . . 119.62(19) ?
N1 C7 C8 . . 103.45(16) ?
N1 C7 C10 . . 123.88(17) ?
C8 C7 C10 . . 132.61(18) ?
O2 C9 O1 . . 124.44(19) ?
O2 C9 C8 . . 122.83(18) ?
O1 C9 C8 . . 112.72(17) ?
N3 C8 C7 . . 108.59(17) ?
N3 C8 C9 . . 119.39(17) ?
C7 C8 C9 . . 132.02(17) ?
C1 C6 C5 . . 121.31(19) ?
C1 C6 N1 . . 118.25(18) ?
C5 C6 N1 . . 120.44(19) ?
N6 C18 C17 . . 109.19(17) ?
N6 C18 C19 . . 121.87(17) ?
C17 C18 C19 . . 128.80(18) ?
O3 C19 O4 . . 124.27(19) ?
O3 C19 C18 . . 123.24(18) ?
O4 C19 C18 . . 112.46(17) ?
N3 N2 N1 . . 106.67(15) ?
C3 C4 C5 . . 121.1(2) ?
C3 C4 H4A . . 119.4 ?
C5 C4 H4A . . 119.4 ?
C4 C3 C2 . . 119.7(2) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C6 C1 C2 . . 118.6(2) ?
C6 C1 H1A . . 120.7 ?
C2 C1 H1A . . 120.7 ?
C16 C11 C12 . . 118.7(2) ?
C16 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
C6 C5 C4 . . 118.4(2) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C14 C15 C16 . . 119.0(2) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C3 C2 C1 . . 120.9(2) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C12 C13 C14 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C13 C12 C11 . . 120.7(3) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C13 C14 C15 . . 120.4(2) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
H5A O5 H5B . . 112(3) ?
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
O4 C19 . 1.309(2) ?
O4 H4 . 0.8200 ?
N1 N2 . 1.352(2) ?
N1 C7 . 1.356(3) ?
N1 C6 . 1.440(2) ?
O1 C9 . 1.306(2) ?
O1 H1 . 0.8200 ?
O2 C9 . 1.201(2) ?
N3 N2 . 1.304(2) ?
N3 C8 . 1.357(2) ?
O3 C19 . 1.200(2) ?
N6 N5 . 1.300(2) ?
N6 C18 . 1.365(3) ?
N4 C17 . 1.349(2) ?
N4 N5 . 1.362(2) ?
N4 C16 . 1.434(2) ?
C17 C18 . 1.367(3) ?
C17 C20 . 1.486(3) ?
C16 C11 . 1.376(3) ?
C16 C15 . 1.380(3) ?
C7 C8 . 1.382(3) ?
C7 C10 . 1.485(3) ?
C9 C8 . 1.475(3) ?
C6 C1 . 1.376(3) ?
C6 C5 . 1.381(3) ?
C18 C19 . 1.474(3) ?
C4 C3 . 1.362(3) ?
C4 C5 . 1.383(3) ?
C4 H4A . 0.9300 ?
C3 C2 . 1.370(3) ?
C3 H3 . 0.9300 ?
C1 C2 . 1.382(3) ?
C1 H1A . 0.9300 ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.9300 ?
C5 H5 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C15 C14 . 1.378(3) ?
C15 H15 . 0.9300 ?
C2 H2 . 0.9300 ?
C13 C12 . 1.370(4) ?
C13 C14 . 1.373(4) ?
C13 H13 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C12 H12 . 0.9300 ?
C14 H14 . 0.9300 ?
O5 H5A . 0.85(4) ?
O5 H5B . 0.83(4) ?
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
O4 H4 N3 1_456 0.82 1.89 2.704(2) 169.9
O1 H1 O5 . 0.82 1.79 2.599(2) 167.7
O5 H5A O2 3_665 0.85(4) 2.07(4) 2.914(3) 171(3)
O5 H5B N6 3_566 0.83(4) 2.20(4) 3.015(3) 171(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656160
2 PubChem 139079354
