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#$Date: 2023-05-10 10:29:45 +0300 (Wed, 10 May 2023) $
#$Revision: 283648 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107165.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_8107165
loop_
_publ_author_name
'Cui, Mengbing'
'Li, Yong'
'Chen, Heng'
'Wang, Hui'
'Zeng, Yan'
_publ_section_title
;
 The crystal structure of 3-amino-5-carboxypyridin-1-ium iodide, C6H7IN2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              605
_journal_page_last               606
_journal_paper_doi               10.1515/ncrs-2022-0168
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C6 H7 N2 O2, I'
_chemical_formula_sum            'C6 H7 I N2 O2'
_chemical_formula_weight         266.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90.036(3)
_cell_angle_beta                 99.808(3)
_cell_angle_gamma                117.724(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4522(4)
_cell_length_b                   7.4741(5)
_cell_length_c                   8.3144(5)
_cell_measurement_reflns_used    5758
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.50
_cell_volume                     402.25(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015) [1]'
_computing_data_collection       'Bruker APEX-II [1]'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015) [1]'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [4]'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8304
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_min         2.496
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.932
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0654 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.7796.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.196
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0156
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0130P)²+0.3857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0362
_refine_ls_wR_factor_ref         0.0367
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1583
_reflns_number_total             1656
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0168_suppl.cif
_cod_data_source_block           1
_cod_database_code               8107165
_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_max   0.695
_shelx_estimated_absorpt_t_min   0.507
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), N1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.8119(4) 0.7150(4) 0.2517(3) 0.0161(5) Uani 1 1 d . . . . .
C2 C 0.6551(3) 0.7259(3) 0.3367(3) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.4644(4) 0.6912(4) 0.2493(3) 0.0169(5) Uani 1 1 d . . . . .
H3 H 0.428817 0.659204 0.133927 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7037(3) 0.7709(4) 0.5048(3) 0.0154(5) Uani 1 1 d . . . . .
H4 H 0.834881 0.794433 0.563597 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3704(4) 0.7457(4) 0.4957(3) 0.0179(5) Uani 1 1 d . . . . .
H5 H 0.268128 0.750234 0.547437 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5610(4) 0.7820(4) 0.5894(3) 0.0155(5) Uani 1 1 d . . . . .
I1 I 0.12489(2) 0.78034(2) 0.87556(2) 0.01748(6) Uani 1 1 d . . . . .
N1 N 0.3326(3) 0.7044(3) 0.3329(3) 0.0188(4) Uani 1 1 d . . . . .
H1 H 0.212402 0.684639 0.277168 0.023 Uiso 1 1 calc R U . . .
N2 N 0.6044(3) 0.8273(4) 0.7538(3) 0.0256(5) Uani 1 1 d . . . . .
H2A H 0.489634 0.795466 0.790863 0.031 Uiso 1 1 d R U . . .
H2B H 0.662993 0.756820 0.801785 0.031 Uiso 1 1 d R U . . .
O1 O 0.7437(3) 0.6601(3) 0.0936(2) 0.0197(4) Uani 1 1 d . . . . .
H1A H 0.843744 0.685455 0.047467 0.030 Uiso 1 1 calc R U . . .
O2 O 0.9831(3) 0.7531(3) 0.3249(2) 0.0241(4) 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'
I I -0.4742 1.8119 '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'
N N 0.0061 0.0033 '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
O1 C1 C2 113.1(2) . .
O2 C1 C2 122.0(2) . .
O2 C1 O1 125.0(2) . .
C3 C2 C1 120.9(2) . .
C4 C2 C1 118.8(2) . .
C4 C2 C3 120.4(2) . .
C2 C3 H3 121.2 . .
N1 C3 C2 117.7(2) . .
N1 C3 H3 121.2 . .
C2 C4 H4 119.7 . .
C2 C4 C6 120.6(2) . .
C6 C4 H4 119.7 . .
C6 C5 H5 120.1 . .
N1 C5 H5 120.1 . .
N1 C5 C6 119.8(2) . .
C5 C6 C4 116.9(2) . .
N2 C6 C4 122.1(2) . .
N2 C6 C5 121.0(2) . .
C3 N1 C5 124.6(2) . .
C3 N1 H1 117.7 . .
C5 N1 H1 117.7 . .
C6 N2 H2A 110.4 . .
C6 N2 H2B 109.2 . .
H2A N2 H2B 108.7 . .
C1 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 C2 1.497(3) .
C1 O1 1.316(3) .
C1 O2 1.216(3) .
C2 C3 1.385(3) .
C2 C4 1.382(3) .
C3 H3 0.9500 .
C3 N1 1.334(3) .
C4 H4 0.9500 .
C4 C6 1.403(3) .
C5 H5 0.9500 .
C5 C6 1.401(3) .
C5 N1 1.340(3) .
C6 N2 1.355(3) .
N1 H1 0.8800 .
N2 H2A 0.8848 .
N2 H2B 0.8846 .
O1 H1A 0.8400 .
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
C1 C2 C3 N1 -179.7(2) . . . .
C1 C2 C4 C6 -179.8(2) . . . .
C2 C3 N1 C5 -1.1(4) . . . .
C2 C4 C6 C5 0.0(3) . . . .
C2 C4 C6 N2 -179.5(2) . . . .
C3 C2 C4 C6 0.0(4) . . . .
C4 C2 C3 N1 0.5(4) . . . .
C6 C5 N1 C3 1.2(4) . . . .
N1 C5 C6 C4 -0.6(3) . . . .
N1 C5 C6 N2 178.9(2) . . . .
O1 C1 C2 C3 -3.4(3) . . . .
O1 C1 C2 C4 176.4(2) . . . .
O2 C1 C2 C3 176.9(2) . . . .
O2 C1 C2 C4 -3.3(4) . . . .
