#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/21/7052144.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_7052144
loop_
_publ_author_name
'Moulton, Brian'
'Luisi, Brian S.'
'Fonari, Marina S.'
'Basok, Stepan S.'
'Ganin, Eduard V.'
'Kravtsov, Victor Ch.'
_publ_section_title
;
 Supramolecular associates of para-aminobenzoic acid with N- and
 N,O-heterocyclic molecules
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              561
_journal_paper_doi               10.1039/b618207k
_journal_volume                  31
_journal_year                    2007
_chemical_formula_moiety         'C16 H38 N4, 2(C7 H6 N O2), H2 O'
_chemical_formula_sum            'C30 H52 N6 O5'
_chemical_formula_weight         576.78
_chemical_melting_point          543.6(5)
_chemical_name_common
;
meso-(5S,12S)-5,7,7,12,14,14-hexamethyl-4,11-diaza-1,8-
diazoniacyclotetradecane bis(4-aminobenzoate) hydrate
;
_chemical_name_systematic
;
meso-(5S,12S)-5,7,7,12,14,14-hexamethyl-4,11-diaza-1,8-diazoniacyclotetradecane
bis(4-aminobenzoate) hydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.7200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0506(13)
_cell_length_b                   12.1200(9)
_cell_length_c                   14.4397(10)
_cell_measurement_reflns_used    3244
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.303
_cell_volume                     3175.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13533
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.86956
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS - Area-Detector Absorption Correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0705P)²+1.4832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2940
_reflns_number_total             3646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b618207k.txt
_cod_data_source_block           m5msad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '270-271 \oC' was changed to
'543.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7052144
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42743(6) 0.25354(9) -0.14574(7) 0.0288(3) Uani 1 1 d . . .
O2 O 0.34192(6) 0.20107(8) -0.07946(7) 0.0269(2) Uani 1 1 d . . .
C1 C 0.37368(7) 0.19207(11) -0.14330(10) 0.0207(3) Uani 1 1 d . . .
C2 C 0.34956(7) 0.10337(11) -0.21800(9) 0.0200(3) Uani 1 1 d . . .
C3 C 0.38673(8) 0.08266(12) -0.28620(10) 0.0235(3) Uani 1 1 d . . .
H3 H 0.4257 0.1280 -0.2878 0.028 Uiso 1 1 calc R . .
C4 C 0.36661(8) -0.00375(12) -0.35112(10) 0.0247(3) Uani 1 1 d . . .
H4 H 0.3917 -0.0149 -0.3964 0.030 Uiso 1 1 calc R . .
C5 C 0.30897(7) -0.07490(11) -0.34982(10) 0.0224(3) Uani 1 1 d . . .
C6 C 0.27029(7) -0.05275(12) -0.28280(10) 0.0236(3) Uani 1 1 d . . .
H6 H 0.2309 -0.0973 -0.2815 0.028 Uiso 1 1 calc R . .
C7 C 0.29057(7) 0.03474(11) -0.21898(10) 0.0222(3) Uani 1 1 d . . .
H7 H 0.2642 0.0483 -0.1755 0.027 Uiso 1 1 calc R . .
N1 N 0.29234(7) -0.16550(11) -0.40910(10) 0.0289(3) Uani 1 1 d . . .
H1N1 H 0.3085(10) -0.1671(14) -0.4585(14) 0.033(5) Uiso 1 1 d . . .
H2N1 H 0.2527(11) -0.2043(16) -0.4092(14) 0.042(5) Uiso 1 1 d . . .
N2 N 0.58377(6) 0.45908(10) -0.04950(9) 0.0217(3) Uani 1 1 d . . .
H1N2 H 0.5589(8) 0.4407(13) -0.1099(12) 0.023(4) Uiso 1 1 d . . .
N3 N 0.49637(6) 0.33297(10) 0.03398(8) 0.0205(3) Uani 1 1 d . . .
H1N3 H 0.5146(9) 0.4007(15) 0.0201(12) 0.033(4) Uiso 1 1 d . . .
H2N3 H 0.4688(10) 0.3027(15) -0.0253(14) 0.039(5) Uiso 1 1 d . . .
C8 C 0.61332(8) 0.57052(12) -0.05127(11) 0.0256(3) Uani 1 1 d . . .
H8A H 0.6481 0.5699 -0.0883 0.031 Uiso 1 1 calc R . .
H8B H 0.6394 0.5936 0.0146 0.031 Uiso 1 1 calc R . .
C9 C 0.64150(8) 0.37339(13) -0.01590(11) 0.0273(3) Uani 1 1 d . . .
H9 H 0.6751 0.3962 0.0472 0.033 Uiso 1 1 calc R . .
C10 C 0.68668(9) 0.35688(15) -0.08686(13) 0.0370(4) Uani 1 1 d . . .
H10A H 0.6539 0.3497 -0.1518 0.055 Uiso 1 1 calc R . .
H10B H 0.7160 0.2913 -0.0695 0.055 Uiso 1 1 calc R . .
H10C H 0.7183 0.4194 -0.0834 0.055 Uiso 1 1 calc R . .
C11 C 0.60575(8) 0.26393(12) -0.00251(11) 0.0267(3) Uani 1 1 d . . .
H11A H 0.6440 0.2081 0.0149 0.032 Uiso 1 1 calc R . .
H11B H 0.5716 0.2429 -0.0648 0.032 Uiso 1 1 calc R . .
C12 C 0.56403(8) 0.26074(12) 0.07347(10) 0.0254(3) Uani 1 1 d . . .
C13 C 0.53923(9) 0.14250(13) 0.08300(13) 0.0352(4) Uani 1 1 d . . .
H13A H 0.5121 0.1404 0.1292 0.053 Uiso 1 1 calc R . .
H13B H 0.5817 0.0955 0.1049 0.053 Uiso 1 1 calc R . .
H13C H 0.5084 0.1172 0.0210 0.053 Uiso 1 1 calc R . .
C14 C 0.61128(9) 0.30528(15) 0.17156(11) 0.0359(4) Uani 1 1 d . . .
H14A H 0.6159 0.3839 0.1675 0.054 Uiso 1 1 calc R . .
H14B H 0.6593 0.2721 0.1883 0.054 Uiso 1 1 calc R . .
H14C H 0.5884 0.2878 0.2205 0.054 Uiso 1 1 calc R . .
C15 C 0.44749(8) 0.34882(12) 0.09613(10) 0.0249(3) Uani 1 1 d . . .
H15A H 0.4765 0.3756 0.1595 0.030 Uiso 1 1 calc R . .
H15B H 0.4262 0.2784 0.1052 0.030 Uiso 1 1 calc R . .
O1W O 0.5000 0.62839(13) 0.2500 0.0264(3) Uani 1 2 d S . .
H1W H 0.5272(11) 0.6745(17) 0.2221(15) 0.057(6) Uiso 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
_geom_angle_publ_flag
O2 C1 O1 122.78(12) . . ?
O2 C1 C2 118.91(12) . . ?
O1 C1 C2 118.28(12) . . ?
C7 C2 C3 117.68(12) . . ?
C7 C2 C1 120.44(12) . . ?
C3 C2 C1 121.82(12) . . ?
C4 C3 C2 121.25(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.00(12) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N1 C5 C4 121.24(13) . . ?
N1 C5 C6 120.83(13) . . ?
C4 C5 C6 117.88(12) . . ?
C7 C6 C5 120.41(13) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 121.72(12) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
C5 N1 H1N1 117.7(12) . . ?
C5 N1 H2N1 117.4(12) . . ?
H1N1 N1 H2N1 120.4(17) . . ?
C8 N2 C9 113.59(11) . . ?
C8 N2 H1N2 107.9(10) . . ?
C9 N2 H1N2 105.5(10) . . ?
C15 N3 C12 117.59(11) . . ?
C15 N3 H1N3 110.8(10) . . ?
C12 N3 H1N3 105.0(10) . . ?
C15 N3 H2N3 108.9(11) . . ?
C12 N3 H2N3 107.1(11) . . ?
H1N3 N3 H2N3 106.9(15) . . ?
N2 C8 C15 110.90(11) . 5_665 ?
N2 C8 H8A 109.5 . . ?
C15 C8 H8A 109.5 5_665 . ?
N2 C8 H8B 109.5 . . ?
C15 C8 H8B 109.5 5_665 . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C11 109.53(11) . . ?
N2 C9 C10 112.51(12) . . ?
C11 C9 C10 109.40(13) . . ?
N2 C9 H9 108.4 . . ?
C11 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 117.28(12) . . ?
C9 C11 H11A 108.0 . . ?
C12 C11 H11A 108.0 . . ?
C9 C11 H11B 108.0 . . ?
C12 C11 H11B 108.0 . . ?
H11A C11 H11B 107.2 . . ?
N3 C12 C14 109.75(12) . . ?
N3 C12 C13 108.91(12) . . ?
C14 C12 C13 111.04(13) . . ?
N3 C12 C11 106.35(11) . . ?
C14 C12 C11 111.46(12) . . ?
C13 C12 C11 109.19(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C8 111.44(11) . 5_665 ?
N3 C15 H15A 109.3 . . ?
C8 C15 H15A 109.3 5_665 . ?
N3 C15 H15B 109.3 . . ?
C8 C15 H15B 109.3 5_665 . ?
H15A C15 H15B 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2755(17) . ?
O2 C1 1.2519(16) . ?
C1 C2 1.4929(19) . ?
C2 C7 1.3947(19) . ?
C2 C3 1.3995(18) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.3689(18) . ?
C5 C6 1.4091(18) . ?
C6 C7 1.3806(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 H1N1 0.860(18) . ?
N1 H2N1 0.89(2) . ?
N2 C8 1.4665(18) . ?
N2 C9 1.4828(18) . ?
N2 H1N2 0.885(16) . ?
N3 C15 1.4892(17) . ?
N3 C12 1.5183(18) . ?
N3 H1N3 0.936(18) . ?
N3 H2N3 0.932(19) . ?
C8 C15 1.504(2) 5_665 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.530(2) . ?
C9 C10 1.539(2) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.5386(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.527(2) . ?
C12 C13 1.528(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C8 1.504(2) 5_665 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O1W H1W 0.932(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N1 O2 0.860(18) 2.073(19) 2.9230(17) 169.5(17) 6
N1 H2N1 O2 0.89(2) 2.10(2) 2.9877(17) 175.7(17) 4_544
N2 H1N2 O1W 0.885(16) 2.162(17) 3.0397(13) 171.8(14) 5_665
N3 H1N3 N2 0.936(18) 2.014(17) 2.7898(16) 139.1(14) .
N3 H2N3 O1 0.932(19) 1.78(2) 2.7039(16) 170.8(16) .
O1W H1W O1 0.932(19) 1.818(19) 2.7373(13) 168.1(19) 5_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175789
