#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2101979.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_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) ; _symmetry_cell_setting triclinic _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 \q/2\q _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/[\s^2^(Fo^2^)+(0.0589P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1183 _reflns_number_gt 1794 _reflns_number_total 3169 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file na0090.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_ _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_ _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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0362(9) .0569(10) .0531(11) -.0154(7) -.0104(8) -.0164(9) O2 .0249(9) .0955(14) .0706(13) -.0115(8) -.0062(8) -.0302(10) O3 .0263(8) .0711(12) .0627(11) -.0086(8) -.0046(8) -.0288(9) C1 .0284(13) .0390(13) .0520(16) -.0068(10) -.0113(11) -.0041(11) C11 .0256(11) .0287(11) .0395(13) -.0045(8) -.0091(9) -.0020(9) C12 .0292(11) .0397(13) .0394(13) -.0055(9) -.0084(10) -.0102(10) C13 .0225(11) .0368(12) .0458(14) -.0028(9) -.0080(10) -.0077(10) C14 .0326(13) .0447(14) .0477(15) -.0094(10) -.0136(11) -.0136(11) C15 .0432(14) .0513(15) .0428(14) -.0104(11) -.0032(11) -.0184(11) C16 .0302(12) .0407(13) .0431(14) -.0069(9) -.0017(10) -.0097(11) N1 .0352(10) .0400(10) .0314(10) -.0076(8) -.0043(8) -.0068(8) C2 .0327(12) .0505(14) .0383(13) -.0092(10) -.0050(10) -.0109(11) C3 .0369(13) .0547(15) .0376(14) .0018(11) -.0092(10) -.0077(11) N4 .0402(10) .0381(11) .0302(10) -.0052(8) -.0068(8) -.0058(8) C5 .0438(13) .0458(14) .0357(13) -.0040(11) -.0112(11) -.0004(11) C51 .0751(19) .0445(16) .0588(18) -.0035(13) .0026(15) -.0007(13) C52 .0541(17) .109(3) .0469(17) .0013(16) -.0197(14) .0063(16) C6 .0519(15) .0468(14) .0280(12) -.0097(11) -.0115(11) .0020(10) C7 .0461(13) .0395(13) .0323(13) -.0094(10) -.0036(10) -.0011(10) C71 .0574(16) .0660(17) .0369(14) -.0035(13) .0032(12) -.0028(12) O4 .0839(15) .0652(13) .0659(14) -.0070(10) -.0030(11) -.0179(10) C41 .124(3) .074(2) .098(3) -.016(2) -.002(2) -.004(2) 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_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_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 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 _cod_database_code 2101979