Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3,5-dicarboxybenzoate), C28H36N4O12
Zhou, Qiang; Ou, Guang-Chuan; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 1205–1206; doi:10.1515/ncrs-2022-0445

data_8107334
_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 f\"ur 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/[\s^2^(Fo^2^)+(0.0680P)^2^+0.1637P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0445_suppl.cif
_cod_data_source_block           1905241_0m_a
_cod_database_code               8107334
_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)
;
_shelx_res_checksum              44594
_shelx_hkl_checksum              94517
_olex2_submission_special_instructions 'No special instructions were received'