#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/19/2101982.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_2101982
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 O4 -)'
_chemical_formula_sum            'C30 H48 N4 O8'
_chemical_formula_weight         592.72
_chemical_name_systematic
;
Meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazayclotetradecane-
3,5-dihydroxybenzoic acid (1/2)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.419(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9162(13)
_cell_length_b                   11.8903(10)
_cell_length_c                   14.5229(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      19.40
_cell_measurement_theta_min      9.59
_cell_volume                     1514.3(3)
_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  .009
_diffrn_reflns_av_sigmaI/netI    .0237
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3595
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        'no decay, variation 0.2'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .094
_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    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          .41
_exptl_crystal_size_mid          .41
_exptl_crystal_size_min          .29
_refine_diff_density_max         .213
_refine_diff_density_min         -.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          .0609
_refine_ls_R_factor_gt           .0419
_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)+(0.0539P)²+0.2636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1116
_reflns_number_gt                2576
_reflns_number_total             3470
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0090.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2101982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y+1/2, z+1/2'
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 .17725(12) .61562(9) .10997(7) .0393(3) Uani d . 1 O
O2 .33606(12) .56332(10) .23823(8) .0509(3) Uani d . 1 O
O3 -.19034(14) .28535(11) .05391(7) .0518(3) Uani d . 1 O
O5 .02568(15) .27834(11) .37796(7) .0540(3) Uani d . 1 O
C1 .21763(15) .55155(12) .17928(9) .0319(3) Uani d . 1 C
C11 .11094(14) .45609(12) .19206(9) .0301(3) Uani d . 1 C
C12 .00825(16) .41599(13) .11550(10) .0355(3) Uani d . 1 C
C13 -.08879(16) .32853(13) .12695(10) .0351(3) Uani d . 1 C
C14 -.08607(16) .28071(13) .21394(10) .0361(3) Uani d . 1 C
C15 .01691(17) .32110(13) .29050(9) .0350(3) Uani d . 1 C
C16 .11514(16) .40886(12) .27973(10) .0331(3) Uani d . 1 C
N1 .49503(13) .33192(9) .50291(8) .0286(2) Uani d . 1 N
C2 .50602(17) .30885(12) .40487(10) .0340(3) Uani d . 1 C
C3 .62426(17) .38170(12) .37278(11) .0371(3) Uani d . 1 C
C5 .70088(15) .58758(12) .35190(9) .0307(3) Uani d . 1 C
N4 .58177(12) .50317(9) .37138(7) .0270(2) Uani d . 1 N
C51 .84959(17) .56789(14) .42040(12) .0453(4) Uani d . 1 C
C52 .72246(19) .57140(14) .25080(10) .0421(4) Uani d . 1 C
C6 .63498(17) .70457(12) .36406(10) .0342(3) Uani d . 1 C
C7 .61803(16) .74121(12) .46240(10) .0344(3) Uani d . 1 C
C71 .5768(2) .86617(14) .46170(15) .0602(5) Uani d . 1 C
H3 -.1907 .3242 .0072 .078 Uiso calc R 1 H
H5 -.0354 .2265 .3766 .081 Uiso calc R 1 H
H12 .0049 .4480 .0567 .043 Uiso calc R 1 H
H14 -.1522 .2223 .2213 .043 Uiso calc R 1 H
H16 .1834 .4358 .3311 .040 Uiso calc R 1 H
H1A .5872 .3216 .5391 .034 Uiso calc R 1 H
H2A .4077 .3223 .3653 .041 Uiso calc R 1 H
H2B .5321 .2304 .3985 .041 Uiso calc R 1 H
H3A .7214 .3711 .4143 .045 Uiso calc R 1 H
H3B .6363 .3588 .3104 .045 Uiso calc R 1 H
H4E .5572 .5203 .4272 .032 Uiso calc R 1 H
H4A .4972 .5127 .3277 .032 Uiso calc R 1 H
H51A .8947 .4985 .4053 .068 Uiso calc R 1 H
H51B .8291 .5640 .4830 .068 Uiso calc R 1 H
H51C .9186 .6288 .4160 .068 Uiso calc R 1 H
H52A .7933 .6263 .2359 .063 Uiso calc R 1 H
H52B .6262 .5804 .2095 .063 Uiso calc R 1 H
H52C .7614 .4973 .2435 .063 Uiso calc R 1 H
H6A .6991 .7593 .3403 .041 Uiso calc R 1 H
H6B .5351 .7085 .3245 .041 Uiso calc R 1 H
H7 .7168 .7312 .5039 .041 Uiso calc R 1 H
H71A .4823 .8784 .4194 .090 Uiso calc R 1 H
H71B .6560 .9094 .4417 .090 Uiso calc R 1 H
H71C .5662 .8891 .5236 .090 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
4 3 -2
2 5 -1
2 4 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
O2 C1 O1 . . 124.51(14) yes
O2 C1 C11 . . 118.36(13) no
O1 C1 C11 . . 117.10(12) no
C16 C11 C12 . . 120.01(13) no
C16 C11 C1 . . 120.22(12) no
C12 C11 C1 . . 119.77(12) no
C13 C12 C11 . . 119.86(13) no
O3 C13 C14 . . 117.10(13) yes
O3 C13 C12 . . 122.11(13) yes
C14 C13 C12 . . 120.79(13) no
C13 C14 C15 . . 119.21(13) no
O5 C15 C16 . . 117.12(12) yes
O5 C15 C14 . . 122.41(14) yes
C16 C15 C14 . . 120.47(13) no
C11 C16 C15 . . 119.67(12) no
C2 N1 C7 . 3_666 112.77(11) no
N1 C2 C3 . . 111.48(12) no
N4 C3 C2 . . 111.81(11) no
N4 C5 C51 . . 109.31(11) no
N4 C5 C52 . . 107.98(11) no
C51 C5 C52 . . 111.23(12) no
N4 C5 C6 . . 106.36(10) no
C51 C5 C6 . . 111.74(12) no
C52 C5 C6 . . 110.05(12) no
C3 N4 C5 . . 117.13(10) no
C7 C6 C5 . . 118.15(12) no
N1 C7 C6 3_666 . 109.76(11) no
N1 C7 C71 3_666 . 113.16(12) no
C6 C7 C71 . . 109.59(13) 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 . 1.2618(17) yes
O2 C1 . 1.2413(16) yes
O3 C13 . 1.3643(16) yes
O5 C15 . 1.3572(17) yes
C1 C11 . 1.5137(19) no
C11 C16 . 1.3860(19) no
C11 C12 . 1.3906(19) no
C12 C13 . 1.382(2) no
C13 C14 . 1.382(2) no
C14 C15 . 1.393(2) no
C15 C16 . 1.389(2) no
N1 C2 . 1.4706(18) yes
N1 C7 3_666 1.4865(17) yes
C2 C3 . 1.502(2) no
C3 N4 . 1.4924(17) yes
C5 N4 . 1.5244(17) yes
C5 C51 . 1.5249(19) no
C5 C52 . 1.5270(19) no
C5 C6 . 1.533(2) no
C6 C7 . 1.527(2) no
C7 N1 3_666 1.4865(17) no
C7 C71 . 1.530(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
N1 H1A O3 4_655 .90 2.33 3.100(2) 143 yes
N4 H4A O2 . .90 1.85 2.742(2) 168 yes
N4 H4E N1 3_666 .90 2.12 2.846(2) 137 yes
O3 H3 O1 3_565 .82 1.87 2.677(2) 168 yes
O5 H5 O1 2_545 .82 1.86 2.676(2) 172 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
O2 C1 C11 C16 . . 21.9(2) yes
O1 C1 C11 C16 . . -156.36(13) yes
O2 C1 C11 C12 . . -158.22(14) yes
O1 C1 C11 C12 . . 23.50(19) yes
C16 C11 C12 C13 . . -.4(2) no
C1 C11 C12 C13 . . 179.72(13) no
C11 C12 C13 O3 . . -179.25(14) no
C11 C12 C13 C14 . . .5(2) no
O3 C13 C14 C15 . . 179.28(14) no
C12 C13 C14 C15 . . -.5(2) no
C13 C14 C15 O5 . . 179.85(14) no
C13 C14 C15 C16 . . .4(2) no
C12 C11 C16 C15 . . .3(2) no
C1 C11 C16 C15 . . -179.83(12) no
O5 C15 C16 C11 . . -179.79(13) no
C14 C15 C16 C11 . . -.3(2) no
C7 N1 C2 C3 3_666 . -178.36(11) no
N1 C2 C3 N4 . . -65.04(15) no
C2 C3 N4 C5 . . 172.57(11) no
C51 C5 N4 C3 . . -53.74(15) no
C52 C5 N4 C3 . . 67.40(15) no
C6 C5 N4 C3 . . -174.52(11) no
N4 C5 C6 C7 . . 68.59(15) no
C51 C5 C6 C7 . . -50.61(17) no
C52 C5 C6 C7 . . -174.69(12) no
C5 C6 C7 N1 . 3_666 -64.77(16) no
C5 C6 C7 C71 . . 170.38(13) no
