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#$Date: 2023-06-09 10:28:29 +0300 (Fri, 09 Jun 2023) $
#$Revision: 284429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107334.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_8107334
loop_
_publ_author_name
'Zhou, Qiang'
'Ou, Guang-Chuan'
_publ_section_title
;
 Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium
 bis(3,5-dicarboxybenzoate), C28H36N4O12
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1205
_journal_page_last               1206
_journal_paper_doi               10.1515/ncrs-2022-0445
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C9 H5 O6, C5 H13 N2'
_chemical_formula_sum            'C14 H18 N2 O6'
_chemical_formula_weight         310.30
_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
_atom_sites_solution_primary     iterative
_cell_angle_alpha                75.207(2)
_cell_angle_beta                 81.618(2)
_cell_angle_gamma                78.579(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4922(11)
_cell_length_b                   8.3435(12)
_cell_length_c                   12.1563(18)
_cell_measurement_reflns_used    2493
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.56
_cell_volume                     716.53(18)
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8047
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.414
_diffrn_reflns_theta_min         1.741
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            corlourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   0.75
_exptl_transmission_factor_min   0.64
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0461
_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)+(0.0680P)²+0.1637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2648
_reflns_number_total             3174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0445_suppl.cif
_cod_data_source_block           1905241_0m_a
_cod_database_code               8107334
_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   0.972
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H6 of O6, All C(H,H) groups, All N(H) groups, All N(H,H)
  groups
 At 1.5 times of:
  H2 of O2
2. Restrained distances
 N1-H1 = N2-H2A = N2-H2B = O6-H6 = O2-H2
 0.86 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C5(H5)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.5432(2) 0.69753(17) 0.65615(12) 0.0417(3) Uani 1 1 d . . . . .
C2 C 0.79566(18) 0.82057(16) 0.24088(10) 0.0330(3) Uani 1 1 d . . . . .
C3 C 0.8915(2) 0.23285(16) 0.48268(11) 0.0372(3) Uani 1 1 d . . . . .
C4 C 0.64456(19) 0.63776(16) 0.55489(11) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.66824(18) 0.75165(15) 0.44945(11) 0.0328(3) Uani 1 1 d . . . . .
H5 H 0.618750 0.864753 0.442448 0.039 Uiso 1 1 calc R U . . .
C6 C 0.76453(17) 0.69831(15) 0.35514(10) 0.0296(3) Uani 1 1 d . . . . .
C7 C 0.83679(18) 0.52861(16) 0.36689(11) 0.0317(3) Uani 1 1 d . . . . .
H7 H 0.902197 0.491384 0.304424 0.038 Uiso 1 1 calc R U . . .
C8 C 0.81226(18) 0.41365(15) 0.47127(11) 0.0321(3) Uani 1 1 d . . . . .
C9 C 0.71634(19) 0.46858(16) 0.56532(11) 0.0347(3) Uani 1 1 d . . . . .
H9 H 0.700284 0.392139 0.635079 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8501(3) -0.1163(2) 0.84942(14) 0.0556(4) Uani 1 1 d . . . . .
H10A H 0.910001 -0.053996 0.780052 0.067 Uiso 1 1 calc R U . . .
H10B H 0.749919 -0.156883 0.828687 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6581(3) 0.1465(3) 0.87629(16) 0.0626(5) Uani 1 1 d . . . . .
H11A H 0.555816 0.116421 0.850033 0.075 Uiso 1 1 calc R U . . .
H11B H 0.724259 0.210483 0.810530 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5872(2) 0.2534(2) 0.96058(18) 0.0659(6) Uani 1 1 d . . . . .
H12A H 0.531113 0.185048 1.028727 0.079 Uiso 1 1 calc R U . . .
H12B H 0.492275 0.342809 0.927909 0.079 Uiso 1 1 calc R U . . .
C13 C 0.7291(3) 0.33153(19) 0.99535(16) 0.0581(5) Uani 1 1 d . . . . .
H13A H 0.782603 0.404295 0.928362 0.070 Uiso 1 1 calc R U . . .
H13B H 0.670720 0.399968 1.048432 0.070 Uiso 1 1 calc R U . . .
C14 C 1.0158(3) 0.2629(2) 1.09482(14) 0.0543(4) Uani 1 1 d . . . . .
H14A H 0.957227 0.327545 1.150106 0.065 Uiso 1 1 calc R U . . .
H14B H 1.079381 0.335704 1.032785 0.065 Uiso 1 1 calc R U . . .
N1 N 0.77895(19) -0.00606(17) 0.92665(10) 0.0447(3) Uani 1 1 d D . . . .
H1 H 0.723(2) -0.062(2) 0.9872(11) 0.054 Uiso 1 1 d D U . . .
N2 N 0.87638(18) 0.20076(14) 1.05010(10) 0.0409(3) Uani 1 1 d D . . . .
H2A H 0.930(2) 0.144(2) 1.0001(13) 0.049 Uiso 1 1 d D U . . .
H2B H 0.821(2) 0.1286(19) 1.1024(12) 0.049 Uiso 1 1 d D U . . .
O1 O 0.5314(2) 0.61182(15) 0.75124(9) 0.0749(5) Uani 1 1 d . . . . .
O2 O 0.4681(3) 0.85440(15) 0.62885(10) 0.0864(6) Uani 1 1 d D . . . .
H2 H 0.416010 0.883790 0.686423 0.130 Uiso 1 1 calc DR U . . .
O3 O 0.72815(15) 0.97527(11) 0.23239(8) 0.0432(3) Uani 1 1 d . . . . .
O4 O 0.88515(18) 0.76383(13) 0.16150(9) 0.0550(3) Uani 1 1 d . . . . .
O5 O 0.98699(18) 0.18757(13) 0.39818(9) 0.0540(3) Uani 1 1 d . . . . .
O6 O 0.8612(2) 0.13295(13) 0.57798(9) 0.0589(4) Uani 1 1 d D . . . .
H6 H 0.905(3) 0.0313(15) 0.5749(18) 0.071 Uiso 1 1 d D U . . .
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
C3 O6 H6 111.1(15) . .
H2A N2 H2B 104.3(17) . .
C14 N2 H2A 109.0(11) . .
C14 N2 H2B 113.0(11) . .
C14 N2 C13 115.95(13) . .
C13 N2 H2A 107.9(12) . .
C13 N2 H2B 106.1(12) . .
C10 N1 H1 109.0(13) . .
C10 N1 C11 114.10(14) . .
C11 N1 H1 110.2(13) . .
C1 O2 H2 109.5 . .
C7 C6 C2 119.48(11) . .
C5 C6 C7 118.81(11) . .
C5 C6 C2 121.71(11) . .
C6 C7 H7 119.6 . .
C6 C7 C8 120.74(11) . .
C8 C7 H7 119.6 . .
C9 C4 C5 119.69(12) . .
C9 C4 C1 119.98(11) . .
C5 C4 C1 120.33(11) . .
O3 C2 C6 118.24(11) . .
O4 C2 O3 123.88(11) . .
O4 C2 C6 117.88(11) . .
C4 C9 H9 120.1 . .
C4 C9 C8 119.85(11) . .
C8 C9 H9 120.1 . .
O5 C3 O6 123.48(12) . .
O5 C3 C8 118.79(11) . .
O6 C3 C8 117.72(12) . .
C7 C8 C3 120.10(11) . .
C9 C8 C7 119.97(11) . .
C9 C8 C3 119.93(11) . .
C6 C5 C4 120.94(11) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
O1 C1 O2 123.57(13) . .
O1 C1 C4 124.48(13) . .
O2 C1 C4 111.95(11) . .
N2 C14 H14A 109.8 . .
N2 C14 H14B 109.8 . .
N2 C14 C10 109.44(13) . 2_757
H14A C14 H14B 108.2 . .
C10 C14 H14A 109.8 2_757 .
C10 C14 H14B 109.8 2_757 .
N2 C13 H13A 109.3 . .
N2 C13 H13B 109.3 . .
N2 C13 C12 111.39(13) . .
H13A C13 H13B 108.0 . .
C12 C13 H13A 109.3 . .
C12 C13 H13B 109.3 . .
N1 C10 C14 110.41(13) . 2_757
N1 C10 H10A 109.6 . .
N1 C10 H10B 109.6 . .
C14 C10 H10A 109.6 2_757 .
C14 C10 H10B 109.6 2_757 .
H10A C10 H10B 108.1 . .
N1 C11 H11A 109.3 . .
N1 C11 H11B 109.3 . .
N1 C11 C12 111.52(14) . .
H11A C11 H11B 108.0 . .
C12 C11 H11A 109.3 . .
C12 C11 H11B 109.3 . .
C13 C12 H12A 108.5 . .
C13 C12 H12B 108.5 . .
C11 C12 C13 115.14(15) . .
C11 C12 H12A 108.5 . .
C11 C12 H12B 108.5 . .
H12A C12 H12B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C2 1.2732(16) .
O4 C2 1.2344(16) .
O5 C3 1.2596(17) .
O6 H6 0.854(10) .
O6 C3 1.2625(16) .
N2 H2A 0.870(9) .
N2 H2B 0.876(9) .
N2 C14 1.476(2) .
N2 C13 1.489(2) .
O1 C1 1.1952(17) .
N1 H1 0.862(9) .
N1 C10 1.454(2) .
N1 C11 1.457(2) .
O2 H2 0.8200 .
O2 C1 1.2965(18) .
C6 C7 1.3906(17) .
C6 C2 1.5168(16) .
C6 C5 1.3875(17) .
C7 H7 0.9300 .
C7 C8 1.3943(17) .
C4 C9 1.3876(18) .
C4 C5 1.3985(17) .
C4 C1 1.4939(18) .
C9 H9 0.9300 .
C9 C8 1.3897(18) .
C3 C8 1.4866(17) .
C5 H5 0.9300 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C10 1.501(3) 2_757
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C12 1.510(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.499(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
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
O5 C3 C8 C7 3.0(2) . . . .
O5 C3 C8 C9 -175.87(14) . . . .
O6 C3 C8 C7 -178.02(14) . . . .
O6 C3 C8 C9 3.1(2) . . . .
N2 C13 C12 C11 -60.23(19) . . . .
N1 C11 C12 C13 67.8(2) . . . .
C6 C7 C8 C9 -0.7(2) . . . .
C6 C7 C8 C3 -179.55(13) . . . .
C7 C6 C2 O3 -179.97(13) . . . .
C7 C6 C2 O4 0.1(2) . . . .
C7 C6 C5 C4 0.4(2) . . . .
C4 C9 C8 C7 0.3(2) . . . .
C4 C9 C8 C3 179.14(13) . . . .
C2 C6 C7 C8 179.22(12) . . . .
C2 C6 C5 C4 -178.47(12) . . . .
C9 C4 C5 C6 -0.8(2) . . . .
C9 C4 C1 O1 7.0(3) . . . .
C9 C4 C1 O2 -172.78(16) . . . .
C5 C6 C7 C8 0.4(2) . . . .
C5 C6 C2 O3 -1.1(2) . . . .
C5 C6 C2 O4 178.88(13) . . . .
C5 C4 C9 C8 0.4(2) . . . .
C5 C4 C1 O1 -172.79(17) . . . .
C5 C4 C1 O2 7.5(2) . . . .
C1 C4 C9 C8 -179.30(13) . . . .
C1 C4 C5 C6 178.98(13) . . . .
C14 N2 C13 C12 -175.88(13) . . . .
C13 N2 C14 C10 178.05(13) . . . 2_757
C10 N1 C11 C12 179.16(15) . . . .
C11 N1 C10 C14 175.55(15) . . . 2_757
