#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/85/2008519.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008519
loop_
_publ_author_name
'Ferguson, George'
'Gregson, Richard M.'
'Glidewell, Christopher'
_publ_section_title
;
 A chain of fused R²₂(10) and R⁴₆(12) rings in
 the hydrogen-bonded structure of
 1,4,8,11-tetraazacyclotetradecane--2,2'-biphenol (1/2)
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              815
_journal_page_last               817
_journal_paper_doi               10.1107/S0108270199001833
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C10 H26 N4 2+, 2C12 H9 O2 1-'
_chemical_formula_moiety         'C10 H26 N4, 2(C12 H9 O2)'
_chemical_formula_sum            'C34 H44 N4 O4'
_chemical_formula_weight         572.73
_chemical_name_systematic
;
1,4,8,11-Tetraazacyclotetradecane--2,2'-biphenol (1/2)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                110.845(8)
_cell_angle_beta                 99.069(12)
_cell_angle_gamma                92.998(9)
_cell_formula_units_Z            1
_cell_length_a                   7.3635(7)
_cell_length_b                   9.8643(10)
_cell_length_c                   11.4142(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      17.58
_cell_measurement_theta_min      9.69
_cell_volume                     759.83(16)
_computing_cell_refinement       'SET4 and CELDIM in CAD-4-PC'
_computing_data_collection       'CAD-4-PC (Enraf-Nonius, 1992)'
_computing_data_reduction        'DATRD2 in NRCVAX96 (Gabe et al., 1989)'
_computing_molecular_graphics
'NRCVAX96, ORTEPII (Johnson, 1976) and PLATON (Spek, 1998)'
_computing_publication_material
'NRCVAX96, SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'NRCVAX96 and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SOLVER in NRCVAX96'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3486
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        'no decay, variation 0.6%'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.144
_refine_ls_extinction_coef       0.054(5)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.043
_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)+(0.0534P)²+0.0479P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.111
_reflns_number_gt                2278
_reflns_number_total             3486
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1271.cif
_cod_data_source_block           9897
_cod_original_cell_volume        759.83(15)
_cod_database_code               2008519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 -.04420(13) .58557(11) .39089(9) .0431(3) Uani d . 1 . . O
O2 -.29128(15) .37552(11) .31274(10) .0482(3) Uani d . 1 . . O
C11 -.19913(18) .57607(15) .18601(13) .0383(3) Uani d . 1 . . C
C12 -.10710(18) .65370(15) .31310(14) .0392(3) Uani d . 1 . . C
C13 -.0866(2) .80692(17) .35782(17) .0536(4) Uani d . 1 . . C
C14 -.1569(3) .88099(19) .2828(2) .0660(5) Uani d . 1 . . C
C15 -.2515(3) .8055(2) .1600(2) .0673(5) Uani d . 1 . . C
C16 -.2703(2) .65546(18) .11294(16) .0536(4) Uani d . 1 . . C
C21 -.22090(18) .41382(15) .12640(13) .0375(3) Uani d . 1 . . C
C22 -.26919(18) .32208(15) .18950(13) .0390(3) Uani d . 1 . . C
C23 -.2983(2) .17186(16) .12475(16) .0502(4) Uani d . 1 . . C
C24 -.2760(2) .11032(18) -.00005(17) .0614(5) Uani d . 1 . . C
C25 -.2219(3) .1978(2) -.06239(16) .0621(5) Uani d . 1 . . C
C26 -.1960(2) .34685(18) .00086(14) .0503(4) Uani d . 1 . . C
N1 .28039(16) .48409(14) .35080(11) .0460(3) Uani d . 1 . . N
C2 .3625(2) .6036(2) .31833(16) .0561(4) Uani d . 1 . . C
C3 .4382(2) .73362(19) .43724(17) .0573(4) Uani d . 1 . . C
N4 .59385(17) .69913(13) .51416(12) .0453(3) Uani d . 1 . . N
C5 .6697(2) .82096(18) .63333(17) .0586(4) Uani d . 1 . . C
C6 .8266(2) .77810(19) .71109(17) .0605(5) Uani d . 1 . . C
C7 .7661(2) .6601(2) .75662(14) .0569(5) Uani d . 1 . . C
H2 -.2119 .4447 .3541 .072 Uiso calc R 1 . . H
H13 -.0236 .8596 .4406 .064 Uiso calc R 1 . . H
H14 -.1407 .9826 .3149 .079 Uiso calc R 1 . . H
H15 -.3019 .8555 .1096 .081 Uiso calc R 1 . . H
H16 -.3326 .6050 .0296 .064 Uiso calc R 1 . . H
H23 -.3334 .1119 .1663 .060 Uiso calc R 1 . . H
H24 -.2974 .0095 -.0424 .074 Uiso calc R 1 . . H
H25 -.2032 .1566 -.1459 .074 Uiso calc R 1 . . H
H26 -.1604 .4054 -.0418 .060 Uiso calc R 1 . . H
H1A .1765 .5109 .3806 .055 Uiso calc R 1 . . H
H1E .3603 .4734 .4143 .055 Uiso calc R 1 . . H
H2A .2688 .6311 .2639 .067 Uiso calc R 1 . . H
H2B .4612 .5700 .2718 .067 Uiso calc R 1 . . H
H3A .4788 .8145 .4145 .069 Uiso calc R 1 . . H
H3B .3415 .7630 .4867 .069 Uiso calc R 1 . . H
H4A .6838 .6738 .4682 .054 Uiso calc R 1 . . H
H5A .5728 .8503 .6825 .070 Uiso calc R 1 . . H
H5B .7149 .9036 .6144 .070 Uiso calc R 1 . . H
H6A .9200 .7446 .6596 .073 Uiso calc R 1 . . H
H6B .8832 .8638 .7846 .073 Uiso calc R 1 . . H
H7A .8646 .6534 .8209 .068 Uiso calc R 1 . . H
H7B .6585 .6854 .7956 .068 Uiso calc R 1 . . H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 -1 2
4 -2 1
3 0 -4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 C11 C16 . . 118.44(14) no
C12 C11 C21 . . 122.76(12) no
C16 C11 C21 . . 118.79(13) no
O1 C12 C11 . . 121.91(12) no
O1 C12 C13 . . 120.03(13) no
C11 C12 C13 . . 118.04(14) no
C12 C13 C14 . . 121.78(16) no
C13 C14 C15 . . 120.27(16) no
C14 C15 C16 . . 119.13(16) no
C11 C16 C15 . . 122.28(16) no
C11 C21 C22 . . 123.33(12) no
C11 C21 C26 . . 119.45(13) no
C22 C21 C26 . . 117.21(13) no
O2 C22 C21 . . 122.07(12) no
O2 C22 C23 . . 118.03(13) no
C21 C22 C23 . . 119.89(13) no
C22 C23 C24 . . 121.00(15) no
C23 C24 C25 . . 120.13(16) no
C24 C25 C26 . . 118.98(16) no
C21 C26 C25 . . 122.72(15) no
C2 N1 C7 . 2_666 115.16(12) no
N1 C2 C3 . . 110.37(13) no
C2 C3 N4 . . 110.53(13) no
C3 N4 C5 . . 112.87(13) no
N4 C5 C6 . . 110.73(13) no
C7 C6 C5 . . 113.55(14) no
N1 C7 C6 2_666 . 111.25(12) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . 1.335(2) yes
O2 C22 . 1.355(2) yes
C11 C12 . 1.413(2) no
C11 C16 . 1.398(2) no
C11 C21 . 1.488(2) no
C12 C13 . 1.404(2) no
C13 C14 . 1.372(2) no
C14 C15 . 1.378(3) no
C15 C16 . 1.374(2) no
C21 C22 . 1.405(2) no
C21 C26 . 1.395(2) no
C22 C23 . 1.388(2) no
C23 C24 . 1.376(2) no
C24 C25 . 1.378(2) no
C25 C26 . 1.375(2) no
N1 C2 . 1.484(2) yes
N1 C7 2_666 1.489(2) yes
C2 C3 . 1.498(2) yes
C3 N4 . 1.462(2) yes
N4 C5 . 1.461(2) yes
C5 C6 . 1.515(2) yes
C6 C7 . 1.508(3) yes
C7 N1 2_666 1.489(2) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O1 . 0.82 1.70 2.486(2) 161 yes
N1 H1A O1 . 0.90 1.82 2.682(2) 159 yes
N1 H1E N4 2_666 0.90 2.15 2.865(2) 135 yes
N4 H4A O1 1_655 0.90 2.40 3.273(2) 165 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 C11 C12 O1 . . 176.34(13) no
C21 C11 C12 O1 . . -4.6(2) no
C16 C11 C12 C13 . . -2.1(2) no
C21 C11 C12 C13 . . 176.96(13) no
O1 C12 C13 C14 . . -176.93(14) no
C11 C12 C13 C14 . . 1.6(2) no
C12 C13 C14 C15 . . 0.3(3) no
C13 C14 C15 C16 . . -1.6(3) no
C14 C15 C16 C11 . . 1.0(3) no
C12 C11 C16 C15 . . 0.9(2) no
C21 C11 C16 C15 . . -178.22(15) no
C16 C11 C21 C26 . . 40.8(2) yes
C12 C11 C21 C26 . . -138.3(2) yes
C16 C11 C21 C22 . . -138.1(2) yes
C12 C11 C21 C22 . . 42.8(2) yes
C26 C21 C22 O2 . . 177.99(13) no
C11 C21 C22 O2 . . -3.2(2) no
C26 C21 C22 C23 . . -2.9(2) no
C11 C21 C22 C23 . . 175.94(13) no
O2 C22 C23 C24 . . -179.19(15) no
C21 C22 C23 C24 . . 1.7(2) no
C22 C23 C24 C25 . . 0.8(3) no
C23 C24 C25 C26 . . -1.8(3) no
C24 C25 C26 C21 . . 0.5(3) no
C22 C21 C26 C25 . . 1.9(2) no
C11 C21 C26 C25 . . -177.02(14) no
C7 N1 C2 C3 2_666 . -168.60(10) yes
N1 C2 C3 N4 . . 65.6(2) yes
C2 C3 N4 C5 . . -178.30(10) yes
C3 N4 C5 C6 . . 178.30(10) yes
N4 C5 C6 C7 . . -64.9(2) yes
C5 C6 C7 N1 . 2_666 72.0(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139056595
