#------------------------------------------------------------------------------ #$Date: 2020-04-10 12:29:30 +0300 (Fri, 10 Apr 2020) $ #$Revision: 250667 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557779.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557779 loop_ _publ_author_name 'Aasen, Arne Jorgen' 'Groth, Per' 'Carvalho, Joan F.' 'Varadarajan, John' 'Klaveness, Jo' _publ_section_title ; Synthesis and Crystal Structure of a Macrotricyclic Chelating Agent ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 133 _journal_page_last 137 _journal_paper_doi 10.3891/acta.chem.scand.49-0133 _journal_volume 49 _journal_year 1995 _chemical_formula_sum 'C40 H62 N10 O4' _chemical_formula_weight 746.98 _chemical_name_common ; 7,23-dibenzy1-3,11,19,27-tetraoxo- 1,4,7,10,13,17,20,23,26,29-decaazatricyclo[27.3.2.213'17]hexatriacontane ; _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 94.44(2) _cell_angle_beta 100.84(2) _cell_angle_gamma 94.26(2) _cell_formula_units_Z 1 _cell_length_a 8.352(2) _cell_length_b 10.195(2) _cell_length_c 12.064(3) _cell_volume 1001.7(4) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _exptl_absorpt_coefficient_mu 0.082 _exptl_crystal_density_diffrn 1.238 _exptl_crystal_F_000 404 _refine_ls_number_reflns 3588 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_gt 0.0472 _cod_data_source_file Acta-Chem-Scand-1995-49-133.cif _cod_data_source_block 1 _cod_depositor_comments ; Said to be measured at low temperature without giving any value for T ; _cod_database_code 1557779 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,-y,-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uiso 0.70388(15) 0.61644(11) 0.63690(10) 1.000 0.0420 . . . . O2 O Uiso 0.13319(14) 0.28298(12) 0.69296(10) 1.000 0.0390 . . . . N1 N Uiso 0.67620(14) 0.00234(11) 0.38794(10) 1.000 0.0210 . . . . N2 N Uiso 0.76378(15) 0.32799(12) 0.45755(10) 1.000 0.0240 . . . . N3 N Uiso 0.85949(15) 0.44679(11) 0.67383(10) 1.000 0.0230 . . . . N4 N Uiso 0.73467(14) 0.33216(11) 0.86797(10) 1.000 0.0220 . . . . N5 N Uiso 0.39850(15) 0.24638(12) 0.73941(11) 1.000 0.0270 . . . . C1 C Uiso 0.71747(19) 0.06602(15) 0.28986(12) 1.000 0.0260 . . . . C2 C Uiso 0.8566(2) 0.1761(2) 0.31460(10) 1.000 0.0310 . . . . C3 C Uiso 0.8039(2) 0.3115(2) 0.34450(10) 1.000 0.0320 . . . . C4 C Uiso 0.63272(18) 0.22987(14) 0.47375(12) 1.000 0.0250 . . . . C5 C Uiso 0.69229(17) 0.09411(14) 0.49164(12) 1.000 0.0230 . . . . C6 C Uiso 0.7213(2) 0.4627(2) 0.48030(10) 1.000 0.0310 . . . . C7 C Uiso 0.75908(18) 0.51478(14) 0.60458(13) 1.000 0.0280 . . . . C8 C Uiso 0.91886(18) 0.49430(14) 0.79234(12) 1.000 0.0240 . . . . C9 C Uiso 0.79389(18) 0.47087(14) 0.86734(12) 1.000 0.0240 . . . . C10 C Uiso 0.58675(19) 0.32362(14) 0.91659(13) 1.000 0.0260 . . . . C11 C Uiso 0.43614(19) 0.34985(14) 0.83291(13) 1.000 0.0280 . . . . C12 C Uiso 0.24743(18) 0.21935(14) 0.67751(13) 1.000 0.0260 . . . . C13 C Uiso 0.86134(19) 0.25733(15) 0.92991(13) 1.000 0.0280 . . . . C14 C Uiso 0.81713(17) 0.11033(14) 0.90730(12) 1.000 0.0230 . . . . C15 C Uiso 0.80770(19) 0.04878(15) 0.79923(13) 1.000 0.0290 . . . . C16 C Uiso 0.7650(2) -0.0855(2) 0.77630(10) 1.000 0.0350 . . . . C17 C Uiso 0.7323(2) -0.1607(2) 0.8615(2) 1.000 0.0370 . . . . C18 C Uiso 0.7428(3) -0.1008(2) 0.9694(2) 1.000 0.0460 . . . . C19 C Uiso 0.7848(2) 0.0343(2) 0.99180(10) 1.000 0.0390 . . . . C20 C Uiso 0.22307(18) 0.10627(15) 0.58479(13) 1.000 0.0280 . . . . Hn3 H Uiso 0.906(6) 0.385(4) 0.646(4) 1.000 0.060(10) . . . . Hn5 H Uiso 0.480(6) 0.198(4) 0.722(4) 1.000 0.070(10) . . . . H2O1 H Uiso 0.111(6) 0.078(4) 0.573(4) 1.000 0.040(10) . . . . H2O2 H Uiso 0.253(6) 0.141(4) 0.523(4) 1.000 0.040(10) . . . . H11 H Uiso 0.627(6) 0.100(4) 0.251(4) 1.000 0.050(10) . . . . H12 H Uiso 0.749(6) -0.007(5) 0.240(4) 1.000 0.010(10) . . . . H15 H Uiso 0.834(6) 0.107(4) 0.740(4) 1.000 0.040(10) . . . . H16 H Uiso 0.758(5) -0.127(4) 0.696(4) 1.000 0.060(10) . . . . H17 H Uiso 0.694(6) -0.264(5) 0.843(4) 1.000 0.070(10) . . . . H18 H Uiso 0.723(5) -0.160(4) 1.037(4) 1.000 0.090(10) . . . . H19 H Uiso 0.793(5) 0.082(4) 1.069(4) 1.000 0.060(10) . . . . H21 H Uiso 0.909(6) 0.180(4) 0.243(4) 1.000 0.050(10) . . . . H22 H Uiso 0.943(6) 0.154(5) 0.365(4) 1.000 0.030(10) . . . . H31 H Uiso 0.897(6) 0.386(5) 0.341(4) 1.000 0.040(10) . . . . H32 H Uiso 0.711(6) 0.329(4) 0.293(4) 1.000 0.040(10) . . . . H41 H Uiso 0.540(6) 0.230(4) 0.414(4) 1.000 0.030(10) . . . . H42 H Uiso 0.607(6) 0.260(4) 0.547(4) 1.000 0.020(10) . . . . H51 H Uiso 0.809(6) 0.108(4) 0.534(4) 1.000 0.020(10) . . . . H52 H Uiso 0.632(6) 0.046(4) 0.537(4) 1.000 0.030(10) . . . . H61 H Uiso 0.608(6) 0.475(4) 0.455(4) 1.000 0.040(10) . . . . H62 H Uiso 0.788(6) 0.516(5) 0.451(4) 1.000 0.040(10) . . . . H81 H Uiso 0.942(6) 0.593(5) 0.798(4) 1.000 0.020(10) . . . . H82 H Uiso 1.015(6) 0.456(4) 0.818(4) 1.000 0.030(10) . . . . H91 H Uiso 0.841(6) 0.513(4) 0.948(4) 1.000 0.020(10) . . . . H92 H Uiso 0.706(6) 0.516(5) 0.838(4) 1.000 0.020(10) . . . . H101 H Uiso 0.594(6) 0.385(4) 0.988(4) 1.000 0.030(10) . . . . H102 H Uiso 0.573(6) 0.241(5) 0.941(4) 1.000 0.020(10) . . . . H111 H Uiso 0.342(6) 0.353(4) 0.868(4) 1.000 0.030(10) . . . . H112 H Uiso 0.445(5) 0.431(5) 0.803(4) 1.000 0.040(10) . . . . H131 H Uiso 0.876(6) 0.287(4) 1.014(4) 1.000 0.030(10) . . . . H132 H Uiso 0.955(6) 0.273(4) 0.902(4) 1.000 0.040(10) . . . . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' International Tables 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 113.88(11) . . . yes C1 N1 C20 111.28(12) . . 2_656 yes C5 N1 C20 108.36(11) . . 2_656 yes C3 N2 C4 113.12(12) . . . yes C3 N2 C6 109.71(12) . . . yes C4 N2 C6 111.06(12) . . . yes C7 N3 C8 121.30(12) . . . yes C9 N4 C10 109.81(11) . . . yes C9 N4 C13 111.62(12) . . . yes C10 N4 C13 110.89(11) . . . yes C11 N5 C12 121.88(13) . . . yes N1 C1 C2 116.91(12) . . . yes C1 C2 C3 114.14(14) . . . no N2 C3 C2 113.79(13) . . . yes C7 N3 Hn3 119(3) . . . no C8 N3 Hn3 118(3) . . . no N2 C4 C5 112.75(12) . . . yes C11 N5 Hn5 120(3) . . . no C12 N5 Hn5 119(3) . . . no N1 C5 C4 115.83(12) . . . yes N2 C6 C7 114.60(13) . . . yes O1 C7 N3 123.20(14) . . . yes N3 C7 C6 116.04(13) . . . yes O1 C7 C6 120.71(14) . . . yes N3 C8 C9 113.86(12) . . . yes N4 C9 C8 114.59(12) . . . yes N4 C10 C11 112.31(12) . . . yes N5 C11 C10 110.60(12) . . . yes N5 C12 C20 116.75(13) . . . yes O2 C12 N5 122.39(14) . . . yes O2 C12 C20 120.86(14) . . . yes N4 C13 C14 111.73(12) . . . yes C13 C14 C15 119.80(13) . . . no C13 C14 C19 121.59(14) . . . no C15 C14 C19 118.62(14) . . . no C14 C15 C16 120.72(14) . . . no C15 C16 C17 120.19(15) . . . no C16 C17 C18 119.57(19) . . . no C17 C18 C19 119.99(19) . . . no C14 C19 C18 120.91(15) . . . no N1 C20 C12 114.41(12) 2_656 . . yes N1 C1 H11 110(3) . . . no N1 C1 H12 105(3) . . . no C2 C1 H11 107(3) . . . no C2 C1 H12 108(3) . . . no H11 C1 H12 109(4) . . . no C1 C2 H21 108(2) . . . no C1 C2 H22 112(3) . . . no C3 C2 H21 109(2) . . . no C3 C2 H22 114(3) . . . no H21 C2 H22 100(4) . . . no N2 C3 H31 107(3) . . . no N2 C3 H32 107(3) . . . no C2 C3 H31 111(3) . . . no C2 C3 H32 111(3) . . . no H31 C3 H32 107(4) . . . no N2 C4 H41 110(3) . . . no N2 C4 H42 105(3) . . . no C5 C4 H41 114(2) . . . no C5 C4 H42 104(2) . . . no H41 C4 H42 111(4) . . . no N1 C5 H51 111(3) . . . no N1 C5 H52 103(3) . . . no C4 C5 H51 107(2) . . . no C4 C5 H52 112(3) . . . no H51 C5 H52 107(4) . . . no N2 C6 H61 115(2) . . . no N2 C6 H62 107(3) . . . no C7 C6 H61 105(3) . . . no C7 C6 H62 102(3) . . . no H61 C6 H62 113(4) . . . no N3 C8 H81 109(3) . . . no N3 C8 H82 108(3) . . . no C9 C8 H81 105(3) . . . no C9 C8 H82 112(3) . . . no H81 C8 H82 110(4) . . . no N4 C9 H91 111(2) . . . no N4 C9 H92 108(3) . . . no C8 C9 H91 109(3) . . . no C8 C9 H92 106(3) . . . no H91 C9 H92 108(4) . . . no N4 C10 H101 114(3) . . . no N4 C10 H102 109(3) . . . no C11 C10 H101 108(3) . . . no C11 C10 H102 110(3) . . . no H101 C10 H102 103(4) . . . no N5 C11 H111 108(3) . . . no N5 C11 H112 108(3) . . . no C10 C11 H111 112(3) . . . no C10 C11 H112 114(3) . . . no H111 C11 H112 104(4) . . . no N4 C13 H131 108(3) . . . no N4 C13 H132 108(3) . . . no C14 C13 H131 111(2) . . . no C14 C13 H132 105(3) . . . no H131 C13 H132 113(4) . . . no C14 C15 H15 117(3) . . . no C16 C15 H15 123(3) . . . no C15 C16 H16 119(2) . . . no C17 C16 H16 121(2) . . . no C16 C17 H17 120(3) . . . no C18 C17 H17 120(3) . . . no C17 C18 H18 120(2) . . . no C19 C18 H18 120(2) . . . no C14 C19 H19 117(2) . . . no C18 C19 H19 123(2) . . . no C12 C20 H2O1 105(3) . . . no C12 C20 H2O2 106(3) . . . no H2O1 C20 H2O2 113(4) . . . no N1 C20 H2O1 111(3) 2_656 . . no N1 C20 H2O2 107(3) 2_656 . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2308(19) . . yes O2 C12 1.227(2) . . yes N1 C1 1.4763(19) . . yes N1 C5 1.4817(19) . . yes N1 C20 1.460(2) . 2_656 yes N2 C3 1.4647(18) . . yes N2 C4 1.478(2) . . yes N2 C6 1.462(2) . . yes N3 C7 1.3395(19) . . yes N3 C8 1.4543(19) . . yes N4 C9 1.4641(19) . . yes N4 C10 1.464(2) . . yes N4 C13 1.473(2) . . yes N5 C11 1.455(2) . . yes N5 C12 1.337(2) . . yes C1 C2 1.524(2) . . no C2 C3 1.517(3) . . no N3 Hn3 0.84(5) . . no C4 C5 1.523(2) . . no N5 Hn5 0.92(5) . . no C6 C7 1.518(2) . . no C8 C9 1.522(2) . . no C10 C11 1.512(2) . . no C12 C20 1.517(2) . . no C13 C14 1.508(2) . . no C14 C19 1.381(2) . . no C14 C15 1.388(2) . . no C15 C16 1.382(3) . . no C16 C17 1.384(3) . . no C17 C18 1.379(3) . . no C18 C19 1.389(3) . . no C1 H11 0.92(5) . . no C1 H12 1.00(5) . . no C2 H21 1.04(5) . . no C2 H22 0.91(5) . . no C3 H31 1.06(5) . . no C3 H32 0.94(5) . . no C4 H41 0.95(5) . . no C4 H42 0.98(5) . . no C5 H51 1.01(5) . . no C5 H52 0.95(5) . . no C6 H61 0.96(5) . . no C6 H62 0.89(5) . . no C8 H81 1.01(5) . . no C8 H82 0.93(5) . . no C9 H91 1.03(5) . . no C9 H92 0.92(5) . . no C10 H101 1.01(5) . . no C10 H102 0.92(5) . . no C11 H111 0.96(5) . . no C11 H112 0.93(5) . . no C13 H131 1.02(5) . . no C13 H132 0.92(5) . . no C15 H15 1.01(5) . . no C16 H16 1.02(5) . . no C17 H17 1.07(5) . . no C18 H18 1.08(4) . . no C19 H19 1.01(5) . . no C20 H2O1 0.94(5) . . no C20 H2O2 0.92(5) . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N3 Hn3 O2 0.84(5) 2.23(5) 2.9148(19) 138(4) 1_655 yes N3 Hn3 N2 0.84(5) 2.37(5) 2.7379(18) 107(4) . yes N5 Hn5 N1 0.92(5) 2.48(4) 2.8250(18) 102(3) 2_656 yes C3 H31 N3 1.06(5) 2.60(5) 3.649(2) 175(4) 2_766 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 35.99(18) . . . . no C20 N1 C1 C2 -86.84(16) 2_656 . . . no C1 N1 C5 C4 40.42(17) . . . . no C20 N1 C5 C4 164.83(12) 2_656 . . . no C1 N1 C20 C12 -63.16(16) . . 2_656 2_656 no C5 N1 C20 C12 170.90(12) . . 2_656 2_656 no C4 N2 C3 C2 -57.76(17) . . . . no C6 N2 C3 C2 177.63(13) . . . . no C3 N2 C4 C5 76.08(16) . . . . no C6 N2 C4 C5 -160.05(11) . . . . no C3 N2 C6 C7 -150.96(14) . . . . no C4 N2 C6 C7 83.25(16) . . . . no C8 N3 C7 O1 -4.0(2) . . . . no C8 N3 C7 C6 173.41(13) . . . . no C7 N3 C8 C9 77.83(17) . . . . no C10 N4 C9 C8 -164.94(12) . . . . no C13 N4 C9 C8 71.67(15) . . . . no C9 N4 C10 C11 78.82(14) . . . . no C13 N4 C10 C11 -157.36(12) . . . . no C9 N4 C13 C14 -166.16(12) . . . . no C10 N4 C13 C14 71.06(15) . . . . no C12 N5 C11 C10 156.03(14) . . . . no C11 N5 C12 O2 2.7(2) . . . . no C11 N5 C12 C20 -178.12(13) . . . . no N1 C1 C2 C3 -86.10(16) . . . . no C1 C2 C3 N2 72.84(15) . . . . no N2 C4 C5 N1 -91.52(15) . . . . no N2 C6 C7 O1 -167.24(14) . . . . no N2 C6 C7 N3 15.3(2) . . . . no N3 C8 C9 N4 58.72(16) . . . . no N4 C10 C11 N5 65.95(15) . . . . no O2 C12 C20 N1 -146.61(14) . . . 2_656 no N5 C12 C20 N1 34.24(19) . . . 2_656 no N4 C13 C14 C15 65.62(18) . . . . no N4 C13 C14 C19 -114.14(16) . . . . no C13 C14 C15 C16 -179.03(15) . . . . no C19 C14 C15 C16 0.8(2) . . . . no C13 C14 C19 C18 179.41(18) . . . . no C15 C14 C19 C18 -0.4(3) . . . . no C14 C15 C16 C17 -0.5(3) . . . . no C15 C16 C17 C18 -0.1(3) . . . . no C16 C17 C18 C19 0.5(3) . . . . no C17 C18 C19 C14 -0.3(3) . . . . no