#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/19/2101979.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_2101979
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(C7 H5 O3 -), 2(C H4 O)'
_chemical_formula_sum            'C32 H56 N4 O8'
_chemical_formula_weight         624.81
_chemical_name_systematic
;
Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane-
3-hydroxybenzoic acid-methanol (1/2/2)
;
_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                79.789(10)
_cell_angle_beta                 80.728(10)
_cell_angle_gamma                80.280(10)
_cell_formula_units_Z            1
_cell_length_a                   8.0814(9)
_cell_length_b                   10.1981(12)
_cell_length_c                   10.7800(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      17.36
_cell_measurement_theta_min      8.73
_cell_volume                     853.89(19)
_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    .0580
_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       -12
_diffrn_reflns_number            3169
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        'no decay, variation 1.0'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .087
_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    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .29
_exptl_crystal_size_min          .21
_refine_diff_density_max         .165
_refine_diff_density_min         -.142
_refine_ls_extinction_coef       .017(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   .943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .943
_refine_ls_R_factor_all          .0996
_refine_ls_R_factor_gt           .0482
_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)+(0.0589P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1183
_reflns_number_gt                1794
_reflns_number_total             3169
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0090.cif
_cod_data_source_block           4
_cod_database_code               2101979
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 .47787(18) .26972(16) .32017(15) .0462(4) Uani d . 1 O
O2 .63698(19) .18684(19) .15680(17) .0612(5) Uani d . 1 O
O3 -.11098(18) .20664(17) .27105(16) .0510(5) Uani d . 1 O
C1 .4970(3) .2153(2) .2215(2) .0393(6) Uani d . 1 C
C11 .3430(2) .18478(19) .1757(2) .0311(5) Uani d . 1 C
C12 .1828(2) .2100(2) .2434(2) .0351(5) Uani d . 1 C
C13 .0424(2) .1816(2) .1993(2) .0347(5) Uani d . 1 C
C14 .0622(3) .1292(2) .0874(2) .0395(6) Uani d . 1 C
C15 .2219(3) .1042(2) .0201(2) .0443(6) Uani d . 1 C
C16 .3614(3) .1321(2) .0638(2) .0378(5) Uani d . 1 C
N1 .6562(2) .48140(17) .32951(15) .0352(4) Uani d . 1 N
C2 .8148(3) .4710(2) .3854(2) .0396(5) Uani d . 1 C
C3 .8140(3) .3725(2) .5072(2) .0435(6) Uani d . 1 C
N4 .6864(2) .42249(17) .60766(16) .0360(4) Uani d . 1 N
C5 .6756(3) .3322(2) .7330(2) .0421(6) Uani d . 1 C
C51 .6327(3) .1976(2) .7142(3) .0623(8) Uani d . 1 C
C52 .8402(3) .3113(3) .7913(3) .0723(9) Uani d . 1 C
C6 .5360(3) .4017(2) .8239(2) .0422(6) Uani d . 1 C
C7 .3546(3) .4242(2) .7943(2) .0396(5) Uani d . 1 C
C71 .2298(3) .4802(3) .9007(2) .0558(7) Uani d . 1 C
O4 .2704(3) .22339(19) .54747(19) .0720(6) Uani d . 1 O
C41 .2467(5) .0892(3) .5848(3) .1010(12) Uani d . 1 C
H3 -.1862 .1979 .2317 .077 Uiso calc R 1 H
H12 .1693 .2459 .3185 .042 Uiso calc R 1 H
H14 -.0316 .1107 .0574 .047 Uiso calc R 1 H
H15 .2353 .0684 -.0550 .053 Uiso calc R 1 H
H16 .4684 .1154 .0178 .045 Uiso calc R 1 H
H1E .5684 .5085 .3865 .042 Uiso calc R 1 H
H1A .6442 .3987 .3170 .042 Uiso calc R 1 H
H2A .8275 .5589 .4021 .048 Uiso calc R 1 H
H2B .9108 .4421 .3249 .048 Uiso calc R 1 H
H3A .7901 .2870 .4923 .052 Uiso calc R 1 H
H3B .9251 .3577 .5347 .052 Uiso calc R 1 H
H4A .7090 .5025 .6194 .043 Uiso calc R 1 H
H51A .5398 .2132 .6655 .093 Uiso calc R 1 H
H51B .6016 .1458 .7956 .093 Uiso calc R 1 H
H51C .7297 .1490 .6697 .093 Uiso calc R 1 H
H52A .9307 .2682 .7364 .108 Uiso calc R 1 H
H52B .8270 .2557 .8730 .108 Uiso calc R 1 H
H52C .8665 .3970 .8011 .108 Uiso calc R 1 H
H6A .5378 .3489 .9080 .051 Uiso calc R 1 H
H6B .5659 .4887 .8284 .051 Uiso calc R 1 H
H7 .3250 .3377 .7844 .048 Uiso calc R 1 H
H71A .2598 .5635 .9136 .084 Uiso calc R 1 H
H71B .2337 .4166 .9778 .084 Uiso calc R 1 H
H71C .1174 .4957 .8778 .084 Uiso calc R 1 H
H4 .3396 .2301 .4829 .108 Uiso calc R 1 H
H41A .3545 .0327 .5786 .151 Uiso calc R 1 H
H41B .1770 .0656 .5303 .151 Uiso calc R 1 H
H41C .1921 .0768 .6711 .151 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 4 -1
3 4 2
3 1 3
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
O2 C1 O1 . . 123.9(2) yes
O2 C1 C11 . . 117.1(2) no
O1 C1 C11 . . 119.00(19) no
C16 C11 C12 . . 119.40(18) no
C16 C11 C1 . . 119.50(18) no
C12 C11 C1 . . 121.09(19) no
C11 C12 C13 . . 120.2(2) no
O3 C13 C14 . . 122.77(18) yes
O3 C13 C12 . . 117.34(19) yes
C14 C13 C12 . . 119.89(19) no
C13 C14 C15 . . 119.9(2) no
C16 C15 C14 . . 120.3(2) no
C15 C16 C11 . . 120.3(2) no
C2 N1 C7 . 2_666 115.56(16) no
N1 C2 C3 . . 111.30(17) no
N4 C3 C2 . . 111.17(18) no
C3 N4 C5 . . 115.45(16) no
N4 C5 C51 . . 108.61(18) no
N4 C5 C52 . . 111.95(19) no
C51 C5 C52 . . 110.5(2) no
N4 C5 C6 . . 107.40(17) no
C51 C5 C6 . . 111.06(18) no
C52 C5 C6 . . 107.30(19) no
C7 C6 C5 . . 118.41(18) no
N1 C7 C6 2_666 . 108.95(17) no
N1 C7 C71 2_666 . 110.52(18) no
C6 C7 C71 . . 111.69(19) 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 C1 . 1.261(3) yes
O2 C1 . 1.248(3) yes
O3 C13 . 1.361(2) yes
C1 C11 . 1.508(3) no
C11 C16 . 1.382(3) no
C11 C12 . 1.387(3) no
C12 C13 . 1.389(3) no
C13 C14 . 1.379(3) no
C14 C15 . 1.381(3) no
C15 C16 . 1.379(3) no
N1 C2 . 1.482(2) yes
N1 C7 2_666 1.506(3) yes
C2 C3 . 1.505(3) no
C3 N4 . 1.468(3) yes
N4 C5 . 1.493(3) yes
C5 C51 . 1.526(3) no
C5 C52 . 1.529(3) no
C5 C6 . 1.535(3) no
C6 C7 . 1.522(3) no
C7 N1 2_666 1.506(3) no
C7 C71 . 1.525(3) no
O4 C41 . 1.392(3) yes
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 2.03 2.815(2) 145 yes
N1 H1A O3 1_655 .90 2.59 3.202(2) 126 yes
N1 H1E N4 2_666 .90 2.06 2.793(2) 138 yes
O3 H3 O2 1_455 .82 1.78 2.596(2) 175 yes
O4 H4 O1 . .82 1.94 2.752(3) 171 yes
C2 H2A O4 2_666 .97 2.36 3.260(3) 155 no
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
O2 C1 C11 C16 . . -2.2(3) yes
O1 C1 C11 C16 . . 176.4(2) yes
O2 C1 C11 C12 . . 178.4(2) yes
O1 C1 C11 C12 . . -3.0(3) yes
C16 C11 C12 C13 . . .4(3) no
C1 C11 C12 C13 . . 179.76(19) no
C11 C12 C13 O3 . . 178.98(19) no
C11 C12 C13 C14 . . -.5(3) no
O3 C13 C14 C15 . . -179.0(2) no
C12 C13 C14 C15 . . .5(3) no
C13 C14 C15 C16 . . -.4(3) no
C14 C15 C16 C11 . . .3(3) no
C12 C11 C16 C15 . . -.3(3) no
C1 C11 C16 C15 . . -179.7(2) no
C7 N1 C2 C3 2_666 . -178.95(18) no
N1 C2 C3 N4 . . -67.5(2) no
C2 C3 N4 C5 . . -179.80(17) no
C3 N4 C5 C51 . . -59.7(2) no
C3 N4 C5 C52 . . 62.6(3) no
C3 N4 C5 C6 . . -179.86(17) no
N4 C5 C6 C7 . . 64.5(2) no
C51 C5 C6 C7 . . -54.2(3) no
C52 C5 C6 C7 . . -175.0(2) no
C5 C6 C7 N1 . 2_666 -63.8(2) no
C5 C6 C7 C71 . . 173.87(19) no
