#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2010328.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_2010328 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1994 _journal_volume 50 _journal_page_first 1982 _journal_page_last 1985 _publ_section_title ; Tetraaza[3.3.3.3]- and Hexaaza[3.3.3.3.3.3]Paracyclophane Derivatives ; loop_ _publ_author_name 'Tinant, Bernard' 'Declercq, Jean-Paul' 'Lepropre, Guy' 'Fastrez, Jacques' _chemical_formula_moiety 'C44 H52 N4 O8' _chemical_formula_sum 'C44 H52 N4 O8' _chemical_formula_weight 764.90 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.6630(10) _cell_length_b 10.1090(10) _cell_length_c 14.8370(10) _cell_angle_alpha 80.760(10) _cell_angle_beta 81.710(10) _cell_angle_gamma 80.710(10) _cell_volume 2126.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.195 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs 0.0691 _refine_ls_wR_factor_obs 0.2002 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 0.4076(2) 0.3950(2) 0.7848(2) 0.0668(6) Uani d . 1 . N C2 0.3106(2) 0.4055(4) 0.7666(2) 0.0744(8) Uani d . 1 . C C3 0.2909(2) 0.5072(3) 0.6825(2) 0.0653(7) Uani d . 1 . C C4 0.3510(2) 0.5039(3) 0.6013(2) 0.0693(8) Uani d . 1 . C C5 0.3296(2) 0.5914(3) 0.5227(2) 0.0715(8) Uani d . 1 . C C6 0.2486(2) 0.6826(3) 0.5235(2) 0.0666(7) Uani d . 1 . C C7 0.1904(2) 0.6875(3) 0.6056(2) 0.0753(8) Uani d . 1 . C C8 0.2113(2) 0.6000(3) 0.6839(2) 0.0719(8) Uani d . 1 . C C9 0.2214(2) 0.7692(4) 0.4360(3) 0.0838(10) Uani d . 1 . C N10 0.3003(2) 0.8261(2) 0.3801(2) 0.0715(7) Uani d . 1 . N C11 0.3269(2) 0.9374(4) 0.4181(2) 0.0757(8) Uani d . 1 . C C12 0.4258(2) 0.9592(3) 0.3866(2) 0.0670(7) Uani d . 1 . C C13 0.4983(2) 0.8636(3) 0.4159(2) 0.0785(9) Uani d . 1 . C C14 0.5896(2) 0.8848(3) 0.3926(2) 0.0783(9) Uani d . 1 . C C15 0.6125(2) 1.0031(3) 0.3393(2) 0.0691(7) Uani d . 1 . C C16 0.5405(3) 1.0971(3) 0.3101(3) 0.0927(11) Uani d . 1 . C C17 0.4486(3) 1.0754(4) 0.3336(3) 0.0969(12) Uani d . 1 . C C18 0.7124(2) 1.0271(4) 0.3186(3) 0.0793(9) Uani d . 1 . C N19 0.7675(2) 0.9330(3) 0.2597(2) 0.0738(7) Uani d . 1 . N C20 0.8675(3) 0.9116(4) 0.2708(3) 0.0865(10) Uani d . 1 . C C21 0.8849(2) 0.8355(3) 0.3648(2) 0.0752(8) Uani d . 1 . C C22 0.8530(3) 0.7130(4) 0.3967(3) 0.0843(10) Uani d . 1 . C C23 0.8712(3) 0.6427(4) 0.4810(3) 0.0852(10) Uani d . 1 . C C24 0.9217(2) 0.6911(3) 0.5371(2) 0.0780(9) Uani d . 1 . C C25 0.9513(2) 0.8153(4) 0.5049(3) 0.0926(11) Uani d . 1 . C C26 0.9343(2) 0.8851(4) 0.4206(3) 0.0916(11) Uani d . 1 . C C27 0.9484(2) 0.6102(5) 0.6264(3) 0.0894(10) Uani d . 1 . C N28 0.8717(2) 0.5458(3) 0.6804(2) 0.0749(7) Uani d . 1 . N C29 0.8039(2) 0.6418(4) 0.7266(3) 0.0795(9) Uani d . 1 . C C30 0.7093(2) 0.5951(3) 0.7538(2) 0.0676(7) Uani d . 1 . C C31 0.6618(2) 0.5628(4) 0.6885(2) 0.0823(9) Uani d . 1 . C C32 0.5718(2) 0.5327(4) 0.7110(2) 0.0826(9) Uani d . 1 . C C33 0.5270(2) 0.5341(3) 0.7995(2) 0.0649(7) Uani d . 1 . C C34 0.5766(3) 0.5611(4) 0.8640(2) 0.0916(11) Uani d . 1 . C C35 0.6664(2) 0.5902(4) 0.8413(2) 0.0900(11) Uani d . 1 . C C36 0.4261(2) 0.5124(3) 0.8215(2) 0.0733(8) Uani d . 1 . C C37 0.4422(3) 0.2688(4) 0.8356(2) 0.0788(9) Uani d . 1 . C C38 0.3921(3) 0.2337(4) 0.9312(3) 0.0932(10) Uani d . 1 . C O39 0.3203(2) 0.2871(3) 0.9623(2) 0.1184(10) Uani d . 1 . O O40 0.4373(3) 0.1315(4) 0.9770(3) 0.215(2) Uani d . 1 . O C41 0.3980(6) 0.0808(7) 1.0680(4) 0.262(5) Uani d . 1 . C H41A 0.4394(6) 0.0048(7) 1.0932(4) 0.114(2) Uiso calc R 1 . H H41B 0.3390(6) 0.0529(7) 1.0650(4) 0.114(2) Uiso calc R 1 . H H41C 0.3892(6) 0.1508(7) 1.1064(4) 0.114(2) Uiso calc R 1 . H C42 0.2909(3) 0.8531(4) 0.2836(2) 0.0798(9) Uani d . 1 . C C43 0.2053(3) 0.9481(4) 0.2555(3) 0.0893(10) Uani d . 1 . C O44 0.1509(2) 1.0162(3) 0.3052(2) 0.1202(10) Uani d . 1 . O O45 0.1949(2) 0.9458(4) 0.1710(2) 0.1388(12) Uani d . 1 . O C46 0.1161(4) 1.0342(7) 0.1344(4) 0.178(3) Uani d . 1 . C H46A 0.1159(4) 1.0235(7) 0.0713(4) 0.114(2) Uiso calc R 1 . H H46B 0.1212(4) 1.1266(7) 0.1381(4) 0.114(2) Uiso calc R 1 . H H46C 0.0593(4) 1.0108(7) 0.1696(4) 0.114(2) Uiso calc R 1 . H C47 0.7485(3) 0.9633(4) 0.1654(2) 0.0918(10) Uani d . 1 . C C48 0.7738(5) 1.0978(7) 0.1132(3) 0.146(2) Uani d . 1 . C O49 0.8362(6) 1.1413(8) 0.1144(4) 0.346(6) Uani d . 1 . O O50 0.7158(3) 1.1490(4) 0.0547(3) 0.182(2) Uani d . 1 . O C51 0.7362(6) 1.2742(6) -0.0017(5) 0.262(5) Uani d . 1 . C H51A 0.6898(6) 1.3046(6) -0.0429(5) 0.114(2) Uiso calc R 1 . H H51B 0.7964(6) 1.2591(6) -0.0367(5) 0.114(2) Uiso calc R 1 . H H51C 0.7358(6) 1.3417(6) 0.0371(5) 0.114(2) Uiso calc R 1 . H C52 0.9012(3) 0.4237(4) 0.7402(3) 0.0886(10) Uani d . 1 . C C53 0.9546(3) 0.4363(5) 0.8164(3) 0.1043(12) Uani d . 1 . C O54 0.9796(3) 0.5374(4) 0.8317(2) 0.1484(14) Uani d . 1 . O O55 0.9709(3) 0.3183(3) 0.8688(2) 0.1500(13) Uani d . 1 . O C56 1.0237(8) 0.3137(8) 0.9471(6) 0.201(4) Uani d . 1 . C H02A 0.306(3) 0.310(4) 0.751(3) 0.114(2) Uiso d . 1 . H H02B 0.261(3) 0.434(4) 0.824(3) 0.114(2) Uiso d . 1 . H H04 0.413(3) 0.435(4) 0.599(3) 0.114(2) Uiso d . 1 . H H05 0.372(3) 0.579(4) 0.464(3) 0.114(2) Uiso d . 1 . H H07 0.135(3) 0.760(4) 0.609(3) 0.114(2) Uiso d . 1 . H H08 0.169(3) 0.605(4) 0.746(3) 0.114(2) Uiso d . 1 . H H09A 0.172(3) 0.835(4) 0.455(3) 0.114(2) Uiso d . 1 . H H09B 0.196(3) 0.719(4) 0.405(3) 0.114(2) Uiso d . 1 . H H11A 0.320(3) 0.916(4) 0.487(3) 0.114(2) Uiso d . 1 . H H11B 0.286(3) 1.024(4) 0.395(3) 0.114(2) Uiso d . 1 . H H13 0.480(3) 0.780(4) 0.456(3) 0.114(2) Uiso d . 1 . H H14 0.645(3) 0.813(4) 0.416(3) 0.114(2) Uiso d . 1 . H H16 0.559(3) 1.173(4) 0.265(3) 0.114(2) Uiso d . 1 . H H17 0.401(3) 1.151(4) 0.319(3) 0.114(2) Uiso d . 1 . H H18A 0.739(3) 1.018(4) 0.377(3) 0.114(2) Uiso d . 1 . H H18B 0.714(3) 1.122(4) 0.287(3) 0.114(2) Uiso d . 1 . H H20A 0.890(3) 0.853(4) 0.219(3) 0.114(2) Uiso d . 1 . H H20B 0.891(3) 1.000(4) 0.264(3) 0.114(2) Uiso d . 1 . H H22 0.815(3) 0.674(4) 0.356(3) 0.114(2) Uiso d . 1 . H H23 0.854(3) 0.560(4) 0.499(3) 0.114(2) Uiso d . 1 . H H25 0.980(3) 0.852(4) 0.554(3) 0.114(2) Uiso d . 1 . H H26 0.959(3) 0.969(4) 0.389(3) 0.114(2) Uiso d . 1 . H H27A 0.971(3) 0.670(4) 0.665(3) 0.114(2) Uiso d . 1 . H H27B 0.995(3) 0.536(4) 0.624(3) 0.114(2) Uiso d . 1 . H H29A 0.795(3) 0.729(4) 0.684(3) 0.114(2) Uiso d . 1 . H H29B 0.824(3) 0.658(4) 0.787(3) 0.114(2) Uiso d . 1 . H H31 0.692(3) 0.574(4) 0.625(3) 0.114(2) Uiso d . 1 . H H32 0.539(3) 0.516(4) 0.663(3) 0.114(2) Uiso d . 1 . H H34 0.554(3) 0.551(4) 0.926(3) 0.114(2) Uiso d . 1 . H H35 0.693(3) 0.615(4) 0.888(3) 0.114(2) Uiso d . 1 . H H56A 1.047(3) 0.235(5) 0.948(3) 0.114(2) Uiso d . 1 . H H56B 0.993(3) 0.390(5) 0.983(3) 0.114(2) Uiso d . 1 . H H56C 1.071(3) 0.388(5) 0.927(3) 0.114(2) Uiso d . 1 . H H36A 0.390(3) 0.586(4) 0.789(3) 0.114(2) Uiso d . 1 . H H36B 0.408(3) 0.505(4) 0.892(3) 0.114(2) Uiso d . 1 . H H37A 0.442(3) 0.192(4) 0.799(3) 0.114(2) Uiso d . 1 . H H37B 0.511(3) 0.269(4) 0.838(3) 0.114(2) Uiso d . 1 . H H42A 0.286(3) 0.774(4) 0.255(3) 0.114(2) Uiso d . 1 . H H42B 0.351(3) 0.888(4) 0.254(3) 0.114(2) Uiso d . 1 . H H47A 0.680(3) 0.958(4) 0.169(3) 0.114(2) Uiso d . 1 . H H47B 0.793(3) 0.872(4) 0.138(3) 0.114(2) Uiso d . 1 . H H52A 0.933(3) 0.369(4) 0.698(3) 0.114(2) Uiso d . 1 . H H52B 0.845(3) 0.382(4) 0.765(3) 0.114(2) Uiso 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 0.0719(15) 0.0658(14) 0.0620(13) -0.0145(11) -0.0121(11) 0.0019(11) C2 0.074(2) 0.083(2) 0.067(2) -0.027(2) -0.015(2) 0.009(2) C3 0.067(2) 0.063(2) 0.067(2) -0.0210(14) -0.0131(14) 0.0014(13) C4 0.071(2) 0.071(2) 0.064(2) -0.0123(15) -0.0076(15) -0.0026(14) C5 0.074(2) 0.077(2) 0.063(2) -0.015(2) -0.0079(15) -0.0041(15) C6 0.065(2) 0.070(2) 0.066(2) -0.0223(14) -0.0125(14) 0.0037(14) C7 0.061(2) 0.077(2) 0.085(2) -0.0163(15) -0.008(2) 0.002(2) C8 0.067(2) 0.080(2) 0.068(2) -0.023(2) -0.0052(15) 0.000(2) C9 0.070(2) 0.098(3) 0.080(2) -0.024(2) -0.016(2) 0.016(2) N10 0.073(2) 0.076(2) 0.0643(15) -0.0182(12) -0.0099(12) 0.0042(12) C11 0.074(2) 0.078(2) 0.073(2) -0.010(2) -0.001(2) -0.011(2) C12 0.074(2) 0.064(2) 0.061(2) -0.0130(14) -0.0050(14) -0.0051(13) C13 0.079(2) 0.061(2) 0.088(2) -0.011(2) -0.005(2) 0.009(2) C14 0.074(2) 0.067(2) 0.088(2) -0.011(2) -0.008(2) 0.006(2) C15 0.076(2) 0.061(2) 0.071(2) -0.0157(14) -0.0073(15) -0.0059(14) C16 0.090(2) 0.067(2) 0.109(3) -0.017(2) -0.009(2) 0.024(2) C17 0.080(2) 0.074(2) 0.124(3) -0.005(2) -0.018(2) 0.024(2) C18 0.080(2) 0.080(2) 0.081(2) -0.026(2) -0.008(2) -0.011(2) N19 0.077(2) 0.076(2) 0.0689(15) -0.0217(13) -0.0011(13) -0.0068(12) C20 0.082(2) 0.092(2) 0.085(2) -0.031(2) 0.005(2) -0.005(2) C21 0.059(2) 0.081(2) 0.085(2) -0.0182(15) -0.001(2) -0.011(2) C22 0.089(2) 0.088(2) 0.082(2) -0.035(2) -0.004(2) -0.013(2) C23 0.089(2) 0.082(2) 0.088(2) -0.034(2) -0.007(2) -0.006(2) C24 0.055(2) 0.088(2) 0.091(2) -0.015(2) -0.007(2) -0.010(2) C25 0.079(2) 0.093(3) 0.116(3) -0.029(2) -0.031(2) -0.010(2) C26 0.077(2) 0.083(2) 0.120(3) -0.028(2) -0.023(2) -0.003(2) C27 0.059(2) 0.111(3) 0.097(3) -0.018(2) -0.015(2) -0.002(2) N28 0.0618(14) 0.074(2) 0.087(2) -0.0067(12) -0.0140(13) -0.0042(13) C29 0.064(2) 0.077(2) 0.098(2) -0.015(2) -0.009(2) -0.009(2) C30 0.066(2) 0.063(2) 0.075(2) -0.0096(13) -0.0150(15) -0.0086(14) C31 0.070(2) 0.108(3) 0.072(2) -0.022(2) 0.002(2) -0.022(2) C32 0.069(2) 0.113(3) 0.072(2) -0.016(2) -0.009(2) -0.028(2) C33 0.064(2) 0.068(2) 0.063(2) -0.0115(13) -0.0091(14) -0.0076(13) C34 0.090(2) 0.133(3) 0.055(2) -0.033(2) -0.008(2) -0.007(2) C35 0.081(2) 0.129(3) 0.069(2) -0.035(2) -0.019(2) -0.011(2) C36 0.071(2) 0.077(2) 0.073(2) -0.015(2) -0.004(2) -0.012(2) C37 0.086(2) 0.076(2) 0.070(2) -0.012(2) -0.010(2) 0.006(2) C38 0.107(3) 0.088(2) 0.075(2) -0.008(2) -0.008(2) 0.008(2) O39 0.123(2) 0.152(3) 0.0649(15) -0.005(2) 0.0022(15) 0.003(2) O40 0.234(4) 0.179(3) 0.131(3) 0.091(3) 0.057(3) 0.090(3) C41 0.336(10) 0.204(7) 0.126(4) 0.101(7) 0.087(6) 0.094(5) C42 0.086(2) 0.086(2) 0.065(2) -0.013(2) -0.012(2) 0.002(2) C43 0.099(3) 0.094(2) 0.067(2) -0.012(2) -0.012(2) 0.010(2) O44 0.125(2) 0.121(2) 0.105(2) 0.017(2) -0.031(2) -0.004(2) O45 0.125(2) 0.202(3) 0.078(2) 0.018(2) -0.034(2) -0.008(2) C46 0.150(5) 0.254(7) 0.115(4) 0.030(5) -0.065(4) 0.001(4) C47 0.108(3) 0.097(3) 0.071(2) -0.032(2) -0.007(2) 0.001(2) C48 0.174(5) 0.191(6) 0.073(3) -0.076(5) -0.016(3) 0.036(3) O49 0.422(10) 0.400(9) 0.263(7) -0.334(9) -0.201(7) 0.227(7) O50 0.201(4) 0.152(3) 0.150(3) -0.003(3) 0.014(3) 0.051(3) C51 0.374(12) 0.145(5) 0.170(6) 0.058(7) 0.094(7) 0.058(5) C52 0.081(2) 0.085(2) 0.098(3) -0.006(2) -0.019(2) -0.006(2) C53 0.100(3) 0.106(3) 0.103(3) -0.009(2) -0.025(2) 0.001(2) O54 0.171(3) 0.149(3) 0.144(3) -0.055(3) -0.082(3) 0.011(2) O55 0.200(4) 0.122(2) 0.122(2) 0.016(2) -0.067(2) 0.006(2) C56 0.287(11) 0.151(7) 0.166(6) 0.033(6) -0.123(7) -0.005(5) 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 C37 . 1.430(4) yes N1 C36 . 1.461(4) yes N1 C2 . 1.469(4) yes C2 C3 . 1.514(4) yes C2 H02A . 1.04(4) ? C2 H02B . 1.09(4) ? C3 C8 . 1.374(4) no C3 C4 . 1.388(4) no C4 C5 . 1.388(4) no C4 H04 . 1.05(4) ? C5 C6 . 1.380(4) no C5 H05 . 1.01(4) ? C6 C7 . 1.386(4) no C6 C9 . 1.512(4) yes C7 C8 . 1.382(4) no C7 H07 . 1.01(4) ? C8 H08 . 1.04(4) ? C9 N10 . 1.464(4) yes C9 H09A . 0.94(4) ? C9 H09B . 0.89(4) ? N10 C42 . 1.437(4) yes N10 C11 . 1.464(4) yes C11 C12 . 1.498(4) yes C11 H11A . 1.00(4) ? C11 H11B . 1.02(4) ? C12 C17 . 1.365(4) no C12 C13 . 1.385(4) no C13 C14 . 1.376(4) no C13 H13 . 1.00(4) ? C14 C15 . 1.384(4) no C14 H14 . 1.06(4) ? C15 C16 . 1.372(4) no C15 C18 . 1.504(4) yes C16 C17 . 1.386(5) no C16 H16 . 0.98(4) ? C17 H17 . 0.97(4) ? C18 N19 . 1.462(4) yes C18 H18A . 0.98(4) ? C18 H18B . 1.01(4) ? N19 C47 . 1.441(4) yes N19 C20 . 1.477(4) yes C20 C21 . 1.514(5) yes C20 H20A . 1.03(4) ? C20 H20B . 0.99(4) ? C21 C26 . 1.373(5) no C21 C22 . 1.383(4) no C22 C23 . 1.375(5) no C22 H22 . 1.03(4) ? C23 C24 . 1.380(5) no C23 H23 . 0.90(4) ? C24 C25 . 1.384(5) no C24 C27 . 1.508(5) yes C25 C26 . 1.370(5) no C25 H25 . 1.03(4) ? C26 H26 . 1.00(4) ? C27 N28 . 1.462(4) yes C27 H27A . 1.02(4) ? C27 H27B . 0.93(4) ? N28 C52 . 1.444(4) yes N28 C29 . 1.451(4) yes C29 C30 . 1.515(4) yes C29 H29A . 1.00(4) ? C29 H29B . 1.02(4) ? C30 C35 . 1.355(5) no C30 C31 . 1.379(4) no C31 C32 . 1.384(4) no C31 H31 . 0.98(4) ? C32 C33 . 1.382(4) no C32 H32 . 0.97(4) ? C33 C34 . 1.367(4) no C33 C36 . 1.511(4) yes C34 C35 . 1.379(5) no C34 H34 . 0.92(4) ? C35 H35 . 0.92(4) ? C36 H36A . 0.95(4) ? C36 H36B . 1.03(4) ? C37 C38 . 1.517(5) yes C37 H37A . 1.02(4) ? C37 H37B . 1.01(4) ? C38 O39 . 1.169(4) yes C38 O40 . 1.285(5) yes O40 C41 . 1.437(5) yes C41 H41A . 0.96 ? C41 H41B . 0.96 ? C41 H41C . 0.96 ? C42 C43 . 1.518(5) yes C42 H42A . 0.98(4) ? C42 H42B . 1.01(4) ? C43 O44 . 1.213(4) yes C43 O45 . 1.289(4) yes O45 C46 . 1.456(5) yes C46 H46A . 0.96 ? C46 H46B . 0.96 ? C46 H46C . 0.96 ? C47 C48 . 1.525(7) yes C47 H47A . 1.00(4) ? C47 H47B . 1.13(4) ? C48 O49 . 1.080(6) yes C48 O50 . 1.293(6) yes O50 C51 . 1.449(6) yes C51 H51A . 0.96 ? C51 H51B . 0.96 ? C51 H51C . 0.96 ? C52 C53 . 1.496(6) yes C52 H52A . 0.93(4) ? C52 H52B . 0.99(4) ? C53 O54 . 1.204(5) yes C53 O55 . 1.323(5) yes O55 C56 . 1.478(8) yes C56 H56A . 0.81(4) ? C56 H56B . 1.01(4) ? C56 H56C . 1.08(4) ? _cod_database_code 2010328