#------------------------------------------------------------------------------
#$Date: 2022-12-13 10:22:53 +0200 (Tue, 13 Dec 2022) $
#$Revision: 279859 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106384.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_8106384
loop_
_publ_author_name
'Sheng, Liang-Quan'
_publ_section_title
;
 Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid,
 C10H9N3O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1021
_journal_page_last               1022
_journal_paper_doi               10.1515/ncrs-2018-0145
_journal_volume                  233
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H9 N3 O2'
_chemical_formula_weight         203.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3976(6)
_cell_length_b                   10.8753(14)
_cell_length_c                   19.678(3)
_cell_measurement_reflns_used    1765
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.79
_cell_volume                     941.1(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4647
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.140
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0522P)²+0.2111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.618
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                1805
_reflns_number_total             2085
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0145_suppl.cif
_cod_data_source_block           C
_cod_database_code               8106384
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2276(7) 1.0820(2) 0.90277(12) 0.0397(6) Uani 1 1 d . . . . .
H1 H 0.267291 1.165992 0.903731 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0353(6) 1.0358(2) 0.85355(12) 0.0389(6) Uani 1 1 d . . . . .
H2 H -0.055460 1.088230 0.822210 0.047 Uiso 1 1 calc R U . . .
C3 C -0.0210(5) 0.9108(2) 0.85129(11) 0.0300(5) Uani 1 1 d . . . . .
C4 C 0.1112(6) 0.8335(2) 0.89834(12) 0.0374(6) Uani 1 1 d . . . . .
H4 H 0.072820 0.749486 0.897004 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3008(6) 0.8819(2) 0.94741(12) 0.0378(6) Uani 1 1 d . . . . .
H5 H 0.389361 0.829461 0.979080 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3623(5) 1.0069(2) 0.95057(11) 0.0335(5) Uani 1 1 d . . . . .
C7 C 0.5688(6) 1.0587(2) 1.00496(12) 0.0408(6) Uani 1 1 d . . . . .
H7A H 0.756288 1.011771 1.006271 0.049 Uiso 1 1 calc R U . . .
H7B H 0.619375 1.143224 0.993988 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4174(6) 1.0540(2) 1.07379(12) 0.0373(6) Uani 1 1 d . . . . .
C9 C -0.3402(7) 0.9171(3) 0.74552(14) 0.0521(8) Uani 1 1 d . . . . .
H9 H -0.303864 0.998521 0.733678 0.062 Uiso 1 1 calc R U . . .
C10 C -0.3375(7) 0.7459(2) 0.79669(14) 0.0471(7) Uani 1 1 d . . . . .
H10 H -0.297610 0.684206 0.828178 0.057 Uiso 1 1 calc R U . . .
N1 N -0.5129(6) 0.8431(2) 0.71143(11) 0.0518(6) Uani 1 1 d . . . . .
N2 N -0.5114(6) 0.7319(2) 0.74443(11) 0.0491(6) Uani 1 1 d . . . . .
N3 N -0.2196(4) 0.86103(17) 0.80043(9) 0.0325(5) Uani 1 1 d . . . . .
O1 O 0.2792(6) 1.15451(18) 1.09051(10) 0.0610(6) Uani 1 1 d . . . . .
H1A H 0.221367 1.149714 1.130039 0.092 Uiso 1 1 calc R U . . .
O2 O 0.4278(8) 0.96670(19) 1.10946(11) 0.0884(10) Uani 1 1 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 121.7(2) . .
C6 C1 H1 119.1 . .
C2 C1 H1 119.1 . .
C1 C2 C3 119.4(2) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C4 C3 C2 120.1(2) . .
C4 C3 N3 119.7(2) . .
C2 C3 N3 120.2(2) . .
C3 C4 C5 119.5(2) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C4 C5 C6 121.5(2) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C1 C6 C5 117.8(2) . .
C1 C6 C7 121.3(2) . .
C5 C6 C7 120.9(2) . .
C8 C7 C6 110.9(2) . .
C8 C7 H7A 109.5 . .
C6 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.0 . .
O2 C8 O1 123.1(2) . .
O2 C8 C7 122.9(2) . .
O1 C8 C7 114.0(2) . .
N1 C9 N3 111.4(2) . .
N1 C9 H9 124.3 . .
N3 C9 H9 124.3 . .
N2 C10 N3 112.3(2) . .
N2 C10 H10 123.9 . .
N3 C10 H10 123.9 . .
C9 N1 N2 107.4(2) . .
C10 N2 N1 106.0(2) . .
C9 N3 C10 102.9(2) . .
C9 N3 C3 128.9(2) . .
C10 N3 C3 128.23(19) . .
C8 O1 H1A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.380(4) .
C1 C2 1.380(4) .
C1 H1 0.9300 .
C2 C3 1.382(3) .
C2 H2 0.9300 .
C3 C4 1.379(3) .
C3 N3 1.434(3) .
C4 C5 1.380(4) .
C4 H4 0.9300 .
C5 C6 1.388(3) .
C5 H5 0.9300 .
C6 C7 1.513(3) .
C7 C8 1.510(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 O2 1.181(3) .
C8 O1 1.293(3) .
C9 N1 1.294(4) .
C9 N3 1.349(3) .
C9 H9 0.9300 .
C10 N2 1.290(3) .
C10 N3 1.357(3) .
C10 H10 0.9300 .
N1 N2 1.373(3) .
O1 H1A 0.8200 .
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 -0.9(4) . . . .
C1 C2 C3 C4 0.8(4) . . . .
C1 C2 C3 N3 -179.9(2) . . . .
C2 C3 C4 C5 -0.3(4) . . . .
N3 C3 C4 C5 -179.6(2) . . . .
C3 C4 C5 C6 -0.1(4) . . . .
C2 C1 C6 C5 0.6(4) . . . .
C2 C1 C6 C7 -179.0(2) . . . .
C4 C5 C6 C1 -0.1(4) . . . .
C4 C5 C6 C7 179.6(2) . . . .
C1 C6 C7 C8 108.8(3) . . . .
C5 C6 C7 C8 -70.9(3) . . . .
C6 C7 C8 O2 86.4(4) . . . .
C6 C7 C8 O1 -94.5(3) . . . .
N3 C9 N1 N2 0.2(4) . . . .
N3 C10 N2 N1 -0.4(3) . . . .
C9 N1 N2 C10 0.1(4) . . . .
N1 C9 N3 C10 -0.4(3) . . . .
N1 C9 N3 C3 -179.2(2) . . . .
N2 C10 N3 C9 0.5(3) . . . .
N2 C10 N3 C3 179.3(2) . . . .
C4 C3 N3 C9 -171.0(3) . . . .
C2 C3 N3 C9 9.7(4) . . . .
C4 C3 N3 C10 10.5(4) . . . .
C2 C3 N3 C10 -168.8(3) . . . .
