#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/19/2101957.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_2101957 loop_ _publ_author_name 'Lough, Alan J.' 'Gregson, Richard M.' 'Ferguson, George' 'Glidewell, Christopher' _publ_section_title ;Two different three-dimensional hydrogen-bonded framework structures in two hydrated adducts meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane--terephthalic acid--water (1/1/4) and (1/1/6) ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 85 _journal_page_last 93 _journal_paper_doi 10.1107/S0108768199011544 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C16 H38 N4,C8 H4 O4,6H2 O' _chemical_formula_sum 'C24 H54 N4 O10' _chemical_formula_weight 558.71 _chemical_name_systematic ; meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra- azacyclotetradecane--terephthalic acid--water (1/1/6) ; _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 116.231(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.1772(3) _cell_length_b 12.3974(4) _cell_length_c 16.8804(5) _cell_measurement_reflns_used 3512 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 4.10 _cell_volume 1535.04(9) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1999)' _computing_publication_material 'NRCVAX96, SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'NRCVAX96 and SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SOLVER in NRCVAX96 (Gabe et al., 1989)' _diffrn_ambient_temperature 100.00(10) _diffrn_measured_fraction_theta_full .997 _diffrn_measured_fraction_theta_max .997 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .040 _diffrn_reflns_av_sigmaI/netI .0378 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 16757 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 4.10 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu .093 _exptl_absorpt_correction_T_max .9780 _exptl_absorpt_correction_T_min .9638 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 612 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .32 _exptl_crystal_size_min .24 _refine_diff_density_max .236 _refine_diff_density_min -.261 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .978 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 3512 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all .977 _refine_ls_R_factor_all .0534 _refine_ls_R_factor_gt .0380 _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^)+(0.0696P)^2^+0.1606P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1077 _reflns_number_gt 2756 _reflns_number_total 3512 _reflns_threshold_expression >2\s(I) _cod_data_source_file bm0023.cif _cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2101957 _cod_database_fobs_code 2101957 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 N1 .43906(13) .34031(7) .45781(6) .0186(2) Uani d . 1 N C2 .34495(16) .37368(9) .36312(7) .0229(3) Uani d . 1 C C3 .46504(17) .44708(9) .33952(8) .0218(3) Uani d . 1 C N4 .48453(13) .55262(7) .38237(6) .0181(2) Uani d . 1 N C5 .62579(15) .62579(9) .37848(7) .0202(2) Uani d . 1 C C51 .59812(18) .64618(11) .28345(8) .0277(3) Uani d . 1 C C52 .81481(16) .57641(10) .43225(8) .0258(3) Uani d . 1 C C6 .60556(16) .73514(9) .41699(8) .0217(2) Uani d . 1 C C7 .66696(16) .74052(9) .51631(8) .0219(3) Uani d . 1 C C71 .64470(19) .85370(10) .54544(9) .0306(3) Uani d . 1 C O11 .86632(13) .20922(7) .61269(6) .0290(2) Uani d . 1 O O12 .75750(11) .25689(6) .47077(5) .0236(2) Uani d . 1 O C11 .92580(15) .09386(9) .51667(7) .0176(2) Uani d . 1 C C12 1.06615(15) .03939(9) .58550(7) .0191(2) Uani d . 1 C C13 1.14005(15) -.05361(9) .56921(7) .0186(2) Uani d . 1 C C14 .84476(16) .19463(9) .53520(8) .0203(2) Uani d . 1 C O3 .90241(12) .36486(7) .73534(6) .0254(2) Uani d D 1 O O4 1.13898(14) .53980(7) .77455(6) .0309(2) Uani d D 1 O O5 .87974(13) .19899(7) .84420(6) .0282(2) Uani d D 1 O H1A .5480 .3116 .4686 .022 Uiso calc R 1 H H1B .4596 .3993 .4920 .022 Uiso calc R 1 H H2A .2327 .4110 .3522 .027 Uiso calc R 1 H H2B .3138 .3101 .3258 .027 Uiso calc R 1 H H3A .5842 .4144 .3585 .026 Uiso calc R 1 H H3B .4116 .4565 .2760 .026 Uiso calc R 1 H H4A .3762 .5866 .3572 .022 Uiso calc R 1 H H51A .5972 .5785 .2556 .042 Uiso calc R 1 H H51B .6958 .6902 .2847 .042 Uiso calc R 1 H H51C .4841 .6825 .2508 .042 Uiso calc R 1 H H52A .8253 .5528 .4885 .039 Uiso calc R 1 H H52B .9067 .6296 .4411 .039 Uiso calc R 1 H H52C .8309 .5160 .4008 .039 Uiso calc R 1 H H6A .6740 .7886 .4020 .026 Uiso calc R 1 H H6B .4782 .7560 .3875 .026 Uiso calc R 1 H H7 .7964 .7211 .5464 .026 Uiso calc R 1 H H71A .5205 .8766 .5126 .046 Uiso calc R 1 H H71B .7238 .9025 .5347 .046 Uiso calc R 1 H H71C .6758 .8532 .6073 .046 Uiso calc R 1 H H12 1.1105 .0657 .6428 .023 Uiso calc R 1 H H13 1.2337 -.0893 .6155 .022 Uiso calc R 1 H H3C .901(2) .3263(14) .6913(9) .054(2) Uiso d D 1 H H3D .984(2) .4159(12) .7468(12) .054(2) Uiso d D 1 H H4C 1.140(3) .5793(13) .7317(9) .054(2) Uiso d D 1 H H4D 1.136(2) .5849(13) .8140(10) .054(2) Uiso d D 1 H H5C .837(2) .2163(15) .8821(10) .054(2) Uiso d D 1 H H5D .889(3) .2556(11) .8152(11) .054(2) Uiso d D 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 N1 .0192(5) .0160(4) .0206(5) .0002(4) .0087(4) -.0018(4) C2 .0244(6) .0204(6) .0189(6) -.0010(5) .0050(5) -.0027(4) C3 .0276(6) .0195(6) .0181(6) .0013(5) .0099(5) -.0009(4) N4 .0174(5) .0169(5) .0197(5) .0011(4) .0078(4) -.0009(4) C5 .0190(5) .0226(6) .0200(6) -.0004(4) .0096(5) .0016(4) C51 .0301(6) .0325(7) .0224(6) -.0001(5) .0132(5) .0039(5) C52 .0201(6) .0308(6) .0255(6) .0025(5) .0091(5) -.0003(5) C6 .0221(6) .0191(5) .0250(6) -.0013(4) .0115(5) .0019(4) C7 .0207(6) .0203(6) .0262(6) -.0037(5) .0117(5) -.0019(4) C71 .0377(7) .0203(6) .0394(8) -.0091(5) .0222(6) -.0067(5) O11 .0462(5) .0216(4) .0258(5) .0051(4) .0219(4) -.0003(3) O12 .0268(4) .0204(4) .0284(5) .0058(3) .0166(4) .0056(3) C11 .0197(5) .0155(5) .0207(6) -.0017(4) .0117(5) .0009(4) C12 .0213(5) .0194(5) .0170(5) -.0020(4) .0088(5) -.0005(4) C13 .0182(5) .0181(5) .0183(5) .0010(4) .0069(4) .0033(4) C14 .0221(5) .0174(5) .0253(6) -.0002(5) .0140(5) .0013(4) O3 .0298(5) .0239(4) .0246(5) -.0012(4) .0140(4) -.0032(3) O4 .0484(6) .0222(5) .0290(5) -.0024(4) .0234(5) -.0007(4) O5 .0405(5) .0237(4) .0274(5) .0004(4) .0214(4) -.0014(4) 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 for Crystallography (199X, Vol C, Tables 4.2.6.8 and 6.1.1.4) ; H H .0000 .0000 ;International Tables for Crystallography (199X, Vol C, Tables 4.2.6.8 and 6.1.1.4) ; N N .0061 .0033 ;International Tables for Crystallography (199X, Vol C, Tables 4.2.6.8 and 6.1.1.4) ; O O .0106 .0060 ;International Tables for Crystallography (199X, Vol C, Tables 4.2.6.8 and 6.1.1.4) ; 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 C2 N1 C7 . 3_666 113.80(10) y N1 C2 C3 . . 111.12(9) no N4 C3 C2 . . 110.32(9) no C3 N4 C5 . . 115.90(10) n N4 C5 C52 . . 109.19(9) no N4 C5 C51 . . 112.69(9) no C52 C5 C51 . . 109.17(10) no N4 C5 C6 . . 106.62(9) no C52 C5 C6 . . 111.66(10) no C51 C5 C6 . . 107.51(9) no C7 C6 C5 . . 117.20(10) no N1 C7 C71 3_666 . 110.60(9) no N1 C7 C6 3_666 . 109.70(9) no C71 C7 C6 . . 111.52(10) no C12 C11 C13 . 3_756 119.32(10) no C12 C11 C14 . . 120.19(10) no C13 C11 C14 3_756 . 120.49(10) no C13 C12 C11 . . 120.56(10) no C12 C13 C11 . 3_756 120.12(10) no O11 C14 O12 . . 125.1(2) n O11 C14 C11 . . 117.60(10) no O12 C14 C11 . . 117.31(10) 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 N1 C2 . 1.494(2) n N1 C7 3_666 1.510(2) n C2 C3 . 1.5155(16) no C3 N4 . 1.469(2) n N4 C5 . 1.493(2) n C5 C52 . 1.5321(16) no C5 C51 . 1.5385(16) no C5 C6 . 1.5437(16) no C6 C7 . 1.5243(16) no C7 N1 3_666 1.5104(14) no C7 C71 . 1.5241(16) no O11 C14 . 1.254(2) n O12 C14 . 1.266(2) n C11 C12 . 1.3945(16) no C11 C13 3_756 1.3965(16) no C11 C14 . 1.5103(15) no C12 C13 . 1.3846(16) no C13 C11 3_756 1.3965(16) 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 O12 . .90 1.83 2.719(2) 170 no N1 H1B N4 3_666 .90 2.05 2.818(2) 142 no O3 H3C O11 . .88(2) 1.90(2) 2.749(2) 161 no O3 H3D O4 . .88(2) 1.91(2) 2.784(2) 172 no N4 H4A O3 3_666 .90 2.20 3.074(2) 163 no O4 H4C O5 2_756 .88(2) 1.92(2) 2.769(2) 163 no O4 H4D O11 2_756 .88(2) 1.98(2) 2.848(2) 169 no O5 H5C O12 4 .88(2) 1.91(2) 2.784(2) 175 no O5 H5D O3 . .88(2) 1.95(2) 2.818(2) 171 no C7 H7 O5 2_756 .98 2.49 3.440(2) 165 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 C7 N1 C2 C3 3_666 . -175.10(10) n N1 C2 C3 N4 . . -70.1(2) n C2 C3 N4 C5 . . 169.20(10) n C3 N4 C5 C52 . . -65.94(12) no C3 N4 C5 C51 . . 55.55(13) no C3 N4 C5 C6 . . 173.30(10) n N4 C5 C6 C7 . . 71.7(2) n C52 C5 C6 C7 . . -47.49(13) no C51 C5 C6 C7 . . -167.21(10) no C5 C6 C7 N1 . 3_666 -58.9(2) n C5 C6 C7 C71 . . 178.25(10) no C13 C11 C12 C13 3_756 . .08(18) no C14 C11 C12 C13 . . 179.39(10) no C11 C12 C13 C11 . 3_756 -.07(18) no C12 C11 C14 O11 . . -20.59(16) no C13 C11 C14 O11 3_756 . 158.72(11) no C12 C11 C14 O12 . . 160.60(10) n C13 C11 C14 O12 3_756 . -20.1(2) n loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063380