#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/19/2101976.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_2101976
loop_
_publ_author_name
'Gregson, Richard M.'
'Glidewell, Christopher'
'Ferguson, George'
'Lough, Alan J.'
_publ_section_title
;
 meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane
 as a building block in supramolecular chemistry; salts formed with
 2,2'-biphenol, 4,4'-biphenol, 4,4'-thiodiphenol,
 4,4'-sulfonyldiphenol, 3- and 4-hydroxybenzoic acids,
 3,5-dihydroxybenzoic acid and phenylphosphonic acid; supramolecular
 structures in zero, one, two and three dimensions
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              39
_journal_page_last               57
_journal_paper_doi               10.1107/S0108768199006072
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C16 H38 N4 2+, 2(C12 H9 O2 -)'
_chemical_formula_sum            'C40 H56 N4 O4'
_chemical_formula_weight         656.89
_chemical_name_systematic
;
Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane-
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                98.783(17)
_cell_angle_beta                 102.785(15)
_cell_angle_gamma                115.746(11)
_cell_formula_units_Z            1
_cell_length_a                   8.6323(19)
_cell_length_b                   9.943(3)
_cell_length_c                   12.582(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      18.58
_cell_measurement_theta_min      7.89
_cell_volume                     909.8(4)
_computing_cell_refinement
'SET4 & CELDIM in CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'DATRD2 in NRCVAX96 (Gabe et al., 1989)'
_computing_molecular_graphics
'NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998)'
_computing_publication_material
'NRCVAX96, SHELXL97  and WordPerfect macro PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'NRCVAX96 and SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294.0(10)
_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     .71073
_diffrn_reflns_av_R_equivalents  .000
_diffrn_reflns_av_sigmaI/netI    .0334
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3375
_diffrn_reflns_theta_full        25.45
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        'no decay, variation  .2'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .077
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             356
_exptl_crystal_size_max          .39
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .17
_refine_diff_density_max         .156
_refine_diff_density_min         -.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          .0854
_refine_ls_R_factor_gt           .0523
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0684P)²+0.0289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1334
_reflns_number_gt                2146
_reflns_number_total             3375
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0090.cif
_cod_data_source_block           1
_cod_database_code               2101976
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_type_symbol
O1 .14207(18) .37187(15) .29777(11) .0556(4) Uani d . 1 O
O2 .0255(2) .16877(17) .39653(12) .0624(4) Uani d . 1 O
C11 -.0941(3) .1455(2) .15110(16) .0475(5) Uani d . 1 C
C12 .0069(3) .3086(2) .19977(16) .0468(5) Uani d . 1 C
C13 -.0374(3) .4035(3) .14253(18) .0586(6) Uani d . 1 C
C14 -.1790(3) .3434(3) .0434(2) .0680(6) Uani d . 1 C
C15 -.2817(3) .1857(3) -.00297(19) .0730(7) Uani d . 1 C
C16 -.2378(3) .0891(3) .05043(18) .0655(6) Uani d . 1 C
C21 -.0495(3) .0348(2) .20023(17) .0501(5) Uani d . 1 C
C22 .0041(3) .0482(2) .31663(18) .0510(5) Uani d . 1 C
C23 .0350(3) -.0651(3) .3548(2) .0617(6) Uani d . 1 C
C24 .0159(3) -.1912(3) .2793(3) .0754(7) Uani d . 1 C
C25 -.0316(4) -.2053(3) .1653(3) .0825(8) Uani d . 1 C
C26 -.0644(3) -.0942(2) .1266(2) .0712(7) Uani d . 1 C
N1 .4893(2) .53683(19) .34399(12) .0486(4) Uani d . 1 N
C2 .5633(3) .7076(2) .38016(18) .0643(6) Uani d . 1 C
C3 .4745(3) .7500(3) .45983(18) .0630(6) Uani d . 1 C
N4 .5138(2) .70499(18) .56377(13) .0489(4) Uani d . 1 N
C5 .4190(3) .7275(2) .64475(17) .0524(5) Uani d . 1 C
C51 .2156(3) .6176(3) .58954(19) .0642(6) Uani d . 1 C
C52 .4538(4) .8961(3) .6791(2) .0860(8) Uani d . 1 C
C6 .4952(3) .6904(3) .75197(17) .0619(6) Uani d . 1 C
C7 .4456(3) .5223(3) .74363(16) .0606(6) Uani d . 1 C
C71 .5275(4) .5047(4) .85817(19) .0989(10) Uani d . 1 C
H2 .0636 .2479 .3757 .094 Uiso calc R 1 H
H13 .0318 .5110 .1728 .070 Uiso calc R 1 H
H14 -.2054 .4097 .0076 .082 Uiso calc R 1 H
H15 -.3797 .1438 -.0695 .088 Uiso calc R 1 H
H16 -.3073 -.0179 .0177 .079 Uiso calc R 1 H
H23 .0689 -.0554 .4323 .074 Uiso calc R 1 H
H24 .0353 -.2669 .3057 .091 Uiso calc R 1 H
H25 -.0418 -.2892 .1141 .099 Uiso calc R 1 H
H26 -.0974 -.1055 .0489 .085 Uiso calc R 1 H
H1A .3673 .4914 .3164 .058 Uiso calc R 1 H
H1E .5175 .5061 .4058 .058 Uiso calc R 1 H
H2A .5419 .7440 .3140 .077 Uiso calc R 1 H
H2B .6934 .7581 .4179 .077 Uiso calc R 1 H
H3A .5186 .8613 .4790 .076 Uiso calc R 1 H
H3B .3441 .6977 .4225 .076 Uiso calc R 1 H
H4A .6343 .7601 .6001 .059 Uiso calc R 1 H
H51A .1671 .6555 .5324 .096 Uiso calc R 1 H
H51B .1565 .6123 .6463 .096 Uiso calc R 1 H
H51C .1951 .5156 .5552 .096 Uiso calc R 1 H
H52A .5823 .9661 .7105 .129 Uiso calc R 1 H
H52B .3968 .9069 .7348 .129 Uiso calc R 1 H
H52C .4041 .9205 .6133 .129 Uiso calc R 1 H
H6A .6267 .7513 .7765 .074 Uiso calc R 1 H
H6B .4555 .7262 .8114 .074 Uiso calc R 1 H
H7 .3130 .4597 .7203 .073 Uiso calc R 1 H
H71A .4878 .3965 .8517 .148 Uiso calc R 1 H
H71B .4885 .5457 .9146 .148 Uiso calc R 1 H
H71C .6577 .5609 .8800 .148 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
0 2 -5
-2 -2 2
-3 0 2
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
C16 C11 C12 . . 117.2(2) no
C16 C11 C21 . . 119.67(19) no
C12 C11 C21 . . 123.08(18) no
O1 C12 C13 . . 120.12(18) yes
O1 C12 C11 . . 121.16(18) yes
C13 C12 C11 . . 118.72(18) no
C14 C13 C12 . . 122.1(2) no
C13 C14 C15 . . 119.9(2) no
C14 C15 C16 . . 119.2(2) no
C15 C16 C11 . . 122.8(2) no
C26 C21 C22 . . 116.7(2) no
C26 C21 C11 . . 118.81(19) no
C22 C21 C11 . . 124.53(18) no
O2 C22 C23 . . 117.1(2) yes
O2 C22 C21 . . 122.25(19) yes
C23 C22 C21 . . 120.6(2) no
C24 C23 C22 . . 120.7(2) no
C25 C24 C23 . . 119.9(2) no
C24 C25 C26 . . 119.7(2) no
C25 C26 C21 . . 122.3(2) no
C2 N1 C7 . 2_666 115.86(16) no
N1 C2 C3 . . 110.43(17) no
N4 C3 C2 . . 110.83(18) no
C3 N4 C5 . . 115.82(16) no
N4 C5 C51 . . 108.78(16) no
N4 C5 C6 . . 106.95(16) no
C51 C5 C6 . . 111.20(18) no
N4 C5 C52 . . 112.33(18) no
C51 C5 C52 . . 109.28(19) no
C6 C5 C52 . . 108.31(18) no
C7 C6 C5 . . 117.79(17) no
N1 C7 C6 2_666 . 109.98(16) no
N1 C7 C71 2_666 . 109.72(19) no
C6 C7 C71 . . 111.2(2) 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 . 1.329(2) yes
O2 C22 . 1.357(2) yes
C11 C16 . 1.394(3) no
C11 C12 . 1.414(3) no
C11 C21 . 1.487(3) no
C12 C13 . 1.398(3) no
C13 C14 . 1.368(3) no
C14 C15 . 1.367(3) no
C15 C16 . 1.384(3) no
C21 C26 . 1.400(3) no
C21 C22 . 1.401(3) no
C22 C23 . 1.393(3) no
C23 C24 . 1.374(3) no
C24 C25 . 1.369(4) no
C25 C26 . 1.383(3) no
N1 C2 . 1.480(3) yes
N1 C7 2_666 1.497(2) yes
C2 C3 . 1.504(3) no
C3 N4 . 1.463(2) yes
N4 C5 . 1.488(2) yes
C5 C51 . 1.523(3) no
C5 C6 . 1.536(3) no
C5 C52 . 1.540(3) no
C6 C7 . 1.514(3) no
C7 N1 2_666 1.497(2) no
C7 C71 . 1.530(3) 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
N1 H1A O1 . .90 1.72 2.584(3) 160 yes
N1 H1E N4 2_666 .90 2.10 2.818(3) 136 yes
O2 H2 O1 . .82 1.70 2.488(2) 162 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 . . 177.59(18) no
C21 C11 C12 O1 . . -4.5(3) no
C16 C11 C12 C13 . . -2.7(3) no
C21 C11 C12 C13 . . 175.21(18) no
O1 C12 C13 C14 . . -177.85(19) no
C11 C12 C13 C14 . . 2.4(3) no
C12 C13 C14 C15 . . -.4(4) no
C13 C14 C15 C16 . . -1.3(4) no
C14 C15 C16 C11 . . .9(4) no
C12 C11 C16 C15 . . 1.1(3) no
C21 C11 C16 C15 . . -176.9(2) no
C16 C11 C21 C26 . . 37.6(3) no
C12 C11 C21 C26 . . -140.2(2) no
C16 C11 C21 C22 . . -141.2(2) no
C12 C11 C21 C22 . . 41.0(3) no
C26 C21 C22 O2 . . 179.21(19) no
C11 C21 C22 O2 . . -2.0(3) no
C26 C21 C22 C23 . . -1.9(3) no
C11 C21 C22 C23 . . 176.93(19) no
O2 C22 C23 C24 . . 179.9(2) no
C21 C22 C23 C24 . . .9(3) no
C22 C23 C24 C25 . . .8(4) no
C23 C24 C25 C26 . . -1.5(4) no
C24 C25 C26 C21 . . .5(4) no
C22 C21 C26 C25 . . 1.2(3) no
C11 C21 C26 C25 . . -177.7(2) no
C7 N1 C2 C3 2_666 . 174.80(17) no
N1 C2 C3 N4 . . 62.7(2) no
C2 C3 N4 C5 . . -174.49(17) no
C3 N4 C5 C51 . . 65.9(2) no
C3 N4 C5 C6 . . -173.95(16) no
C3 N4 C5 C52 . . -55.2(2) no
N4 C5 C6 C7 . . -70.1(2) no
C51 C5 C6 C7 . . 48.5(2) no
C52 C5 C6 C7 . . 168.59(19) no
C5 C6 C7 N1 . 2_666 59.9(2) no
C5 C6 C7 C71 . . -178.34(18) no
