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#$Date: 2023-02-08 12:15:16 +0200 (Wed, 08 Feb 2023) $
#$Revision: 280825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106724.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_8106724
loop_
_publ_author_name
'Zeng, Huahui'
'Shen, Qianjin'
_publ_section_title
;
 Crystal structure of trimethyammonium 2,6-dicarboxyisonicotinate
 monohydrate, C11H16N2O7
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              929
_journal_page_last               930
_journal_paper_doi               10.1515/ncrs-2017-0085
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C8 H5 N O6, C3 H10 N, H2 O'
_chemical_formula_sum            'C11 H16 N2 O7'
_chemical_formula_weight         288.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.753(3)
_cell_length_b                   6.9471(15)
_cell_length_c                   13.797(3)
_cell_measurement_reflns_used    1091
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      3.27
_cell_volume                     1318.2(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.925
_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  0.0149
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2337
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.962
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.004(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.671
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1176
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.670
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0386
_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)+(0.1819P)²+0.8471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1650
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                952
_reflns_number_total             1176
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0085_suppl.cif
_cod_data_source_block           2
_cod_database_code               8106724
_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   0.963
_shelx_estimated_absorpt_t_max   0.989
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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
O1 O -0.00104(13) 0.7500 -0.24357(14) 0.0512(6) Uani 1 2 d DS T P . .
H1 H -0.050(2) 0.7500 -0.205(2) 0.077 Uiso 1 2 d DS U P . .
C1 C 0.08627(15) 0.7500 -0.0920(2) 0.0311(6) Uani 1 2 d S T P . .
O1W O 0.16822(18) 0.2500 0.1588(2) 0.1134(16) Uani 1 2 d DS T P . .
H1WA H 0.2249(19) 0.2500 0.184(4) 0.170 Uiso 1 2 d DS U P . .
H1WB H 0.171(4) 0.204(12) 0.101(2) 0.170 Uiso 0.5 1 d D U P . .
N1 N 0.00062(13) 0.7500 -0.04626(15) 0.0293(5) Uani 1 2 d S T P . .
O2 O 0.15759(15) 0.7500 -0.24728(16) 0.0771(9) Uani 1 2 d S T P . .
C2 C 0.08378(17) 0.7500 -0.2003(2) 0.0427(7) Uani 1 2 d S T P . .
N2 N 0.13312(14) 0.7500 0.42134(15) 0.0358(6) Uani 1 2 d S T P . .
H2 H 0.1964 0.7500 0.4264 0.043 Uiso 1 2 d R U P . .
O3 O -0.17174(12) 0.7500 0.04999(15) 0.0445(6) Uani 1 2 d S T P . .
C3 C 0.17511(16) 0.7500 -0.04319(19) 0.0328(6) Uani 1 2 d S T P . .
H3A H 0.2334 0.7500 -0.0774 0.039 Uiso 1 2 calc R U P . .
O4 O -0.09335(12) 0.7500 0.19156(16) 0.0584(7) Uani 1 2 d S T P . .
C4 C 0.17479(16) 0.7500 0.05624(19) 0.0310(6) Uani 1 2 d S T P . .
C5 C 0.08616(14) 0.7500 0.1041(2) 0.0319(6) Uani 1 2 d S T P . .
H5A H 0.0838 0.7500 0.1714 0.038 Uiso 1 2 calc R U P . .
O5 O 0.25857(12) 0.7500 0.20436(14) 0.0527(7) Uani 1 2 d DS T P . .
H5 H 0.3125(16) 0.7500 0.237(2) 0.079 Uiso 1 2 d DS U P . .
C6 C 0.00097(15) 0.7500 0.04994(19) 0.0286(6) Uani 1 2 d S T P . .
O6 O 0.34730(12) 0.7500 0.06927(15) 0.0526(6) Uani 1 2 d S T P . .
C7 C -0.09705(15) 0.7500 0.1010(2) 0.0333(6) Uani 1 2 d S T P . .
C8 C 0.26997(16) 0.7500 0.1110(2) 0.0354(6) Uani 1 2 d S T P . .
C9 C 0.10307(14) 0.5741(3) 0.36902(16) 0.0470(6) Uani 1 1 d . . . . .
H9A H 0.1377 0.5660 0.3087 0.070 Uiso 1 1 calc R U . . .
H9B H 0.0345 0.5790 0.3565 0.070 Uiso 1 1 calc R U . . .
H9C H 0.1176 0.4631 0.4078 0.070 Uiso 1 1 calc R U . . .
C11 C 0.0954(2) 0.7500 0.5219(2) 0.0535(9) Uani 1 2 d S T P . .
H11A H 0.1178 0.6373 0.5553 0.064 Uiso 1 1 d R U . . .
H11B H 0.0257 0.7500 0.5201 0.064 Uiso 1 2 d R U P . .
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
C2 O1 H1 115(3) . .
N1 C1 C3 122.9(3) . .
N1 C1 C2 116.9(2) . .
C3 C1 C2 120.2(2) . .
H1WA O1W H1WB 110(3) . .
C6 N1 C1 118.0(2) . .
O2 C2 O1 120.3(3) . .
O2 C2 C1 121.2(2) . .
O1 C2 C1 118.4(2) . .
C9 N2 C9 111.5(2) 8_575 .
C9 N2 C11 111.06(14) 8_575 .
C9 N2 C11 111.06(14) . .
C9 N2 H2 108.5 8_575 .
C9 N2 H2 108.5 . .
C11 N2 H2 105.9 . .
C4 C3 C1 118.7(2) . .
C4 C3 H3A 120.7 . .
C1 C3 H3A 120.7 . .
C3 C4 C5 118.6(2) . .
C3 C4 C8 119.8(2) . .
C5 C4 C8 121.6(2) . .
C4 C5 C6 119.0(3) . .
C4 C5 H5A 120.5 . .
C6 C5 H5A 120.5 . .
C8 O5 H5 114(3) . .
N1 C6 C5 122.7(2) . .
N1 C6 C7 117.4(2) . .
C5 C6 C7 119.9(2) . .
O3 C7 O4 126.8(2) . .
O3 C7 C6 118.0(3) . .
O4 C7 C6 115.3(2) . .
O6 C8 O5 125.4(2) . .
O6 C8 C4 121.6(2) . .
O5 C8 C4 113.0(2) . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N2 C11 H11A 109.7 . .
N2 C11 H11B 109.1 . .
H11A C11 H11B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.310(3) .
O1 H1 0.863(10) .
C1 N1 1.336(3) .
C1 C3 1.395(3) .
C1 C2 1.494(5) .
O1W H1WA 0.857(10) .
O1W H1WB 0.856(10) .
N1 C6 1.327(4) .
O2 C2 1.204(3) .
N2 C9 1.478(2) 8_575
N2 C9 1.478(2) .
N2 C11 1.481(4) .
N2 H2 0.8737 .
O3 C7 1.246(3) .
C3 C4 1.372(4) .
C3 H3A 0.9300 .
O4 C7 1.250(4) .
C4 C5 1.386(3) .
C4 C8 1.511(3) .
C5 C6 1.389(3) .
C5 H5A 0.9300 .
O5 C8 1.298(4) .
O5 H5 0.867(10) .
C6 C7 1.521(3) .
O6 C8 1.209(3) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C11 H11A 0.9594 .
C11 H11B 0.9590 .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{e764865f-1060-45de-83be-8369a8ce303e} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{e764865f-1060-45de-83be-8369a8ce303e} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
CE
