data_2013216 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2003 _journal_volume 59 _journal_page_first o147 _journal_page_last o149 _publ_section_title ; Meso-5,5,7,12,12,14-hexamethyl-1,4-diaza-8,11-diazoniumcyclotetradecane bis(2-naphthoate) ethanol disolvate: centrosymmetric five-component aggregates linked into sheets by C-H...\p(arene) hydrogen bonding ; loop_ _publ_author_name 'Bowes, Katharine F.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _chemical_formula_moiety 'C16 H38 N4 2+ , 2C11 H7 O2 - , 2C2 H6 O' _chemical_formula_sum 'C42 H64 N4 O6' _chemical_formula_weight 720.97 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 10.9563(4) _cell_length_b 10.9584(5) _cell_length_c 17.1665(8) _cell_angle_alpha 90 _cell_angle_beta 101.446(2) _cell_angle_gamma 90 _cell_volume 2020.08(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(10) _exptl_crystal_density_diffrn 1.185 _diffrn_ambient_temperature 150.0(10) 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.59018(11) 0.52392(11) 0.61507(7) 0.0312(3) Uani d . 1 . . N C2 0.57058(15) 0.39781(14) 0.64207(9) 0.0356(4) Uani d . 1 . . C C3 0.43695(15) 0.35860(15) 0.61481(9) 0.0370(4) Uani d . 1 . . C N4 0.40393(11) 0.35695(11) 0.52786(7) 0.0325(3) Uani d . 1 . . N C5 0.27070(14) 0.33163(15) 0.49161(9) 0.0361(4) Uani d . 1 . . C C51 0.22189(17) 0.21533(17) 0.52546(11) 0.0480(4) Uani d . 1 . . C C52 0.19147(15) 0.44189(17) 0.50605(10) 0.0439(4) Uani d . 1 . . C C6 0.26297(15) 0.31186(15) 0.40202(9) 0.0368(4) Uani d . 1 . . C C7 0.28454(14) 0.42168(15) 0.35181(9) 0.0348(4) Uani d . 1 . . C C71 0.27610(16) 0.38570(16) 0.26513(9) 0.0429(4) Uani d . 1 . . C O1 0.41503(11) 0.66378(11) 0.65109(7) 0.0457(3) Uani d . 1 . . O O2 0.37126(11) 0.75854(11) 0.53397(7) 0.0440(3) Uani d . 1 . . O C11 0.21341(14) 0.76163(13) 0.70018(9) 0.0320(3) Uani d . 1 . . C C12 0.23857(13) 0.79095(13) 0.62741(9) 0.0310(3) Uani d . 1 . . C C13 0.16199(14) 0.87711(15) 0.57892(9) 0.0365(4) Uani d . 1 . . C C14 0.06376(14) 0.93073(15) 0.60461(9) 0.0385(4) Uani d . 1 . . C C15 -0.06156(15) 0.95855(16) 0.70949(11) 0.0430(4) Uani d . 1 . . C C16 -0.07952(16) 0.93351(17) 0.78424(11) 0.0466(4) Uani d . 1 . . C C17 -0.00250(16) 0.84944(16) 0.83312(10) 0.0432(4) Uani d . 1 . . C C18 0.09168(15) 0.79137(15) 0.80623(10) 0.0376(4) Uani d . 1 . . C C19 0.11366(13) 0.81656(13) 0.72887(9) 0.0319(3) Uani d . 1 . . C C110 0.03700(14) 0.90262(14) 0.68001(9) 0.0348(4) Uani d . 1 . . C C111 0.34968(14) 0.73366(14) 0.60124(9) 0.0340(3) Uani d . 1 . . C O3 0.32676(12) 0.89822(12) 0.39975(7) 0.0528(3) Uani d . 1 . . O C31 0.43030(16) 0.97600(16) 0.39884(10) 0.0444(4) Uani d . 1 . . C C32 0.42512(18) 1.02307(18) 0.31655(10) 0.0500(5) Uani d . 1 . . C H1A 0.5300 0.5736 0.6287 0.037 Uiso calc R 1 . . H H1B 0.5788 0.5237 0.5605 0.037 Uiso calc R 1 . . H H2A 0.5928 0.3942 0.7008 0.043 Uiso calc R 1 . . H H2B 0.6258 0.3409 0.6206 0.043 Uiso calc R 1 . . H H3A 0.4252 0.2762 0.6357 0.044 Uiso calc R 1 . . H H3B 0.3815 0.4157 0.6359 0.044 Uiso calc R 1 . . H H4 0.4522 0.2989 0.5097 0.039 Uiso calc R 1 . . H H51A 0.2711 0.1450 0.5146 0.072 Uiso calc R 1 . . H H51B 0.1344 0.2028 0.5004 0.072 Uiso calc R 1 . . H H51C 0.2291 0.2242 0.5830 0.072 Uiso calc R 1 . . H H52A 0.1888 0.4469 0.5627 0.066 Uiso calc R 1 . . H H52B 0.1067 0.4324 0.4750 0.066 Uiso calc R 1 . . H H52C 0.2284 0.5167 0.4897 0.066 Uiso calc R 1 . . H H6A 0.3246 0.2484 0.3956 0.044 Uiso calc R 1 . . H H6B 0.1795 0.2784 0.3795 0.044 Uiso calc R 1 . . H H7 0.2191 0.4842 0.3547 0.042 Uiso calc R 1 . . H H71A 0.2876 0.4582 0.2340 0.064 Uiso calc R 1 . . H H71B 0.1941 0.3499 0.2443 0.064 Uiso calc R 1 . . H H71C 0.3411 0.3258 0.2614 0.064 Uiso calc R 1 . . H H11 0.2641 0.7030 0.7323 0.038 Uiso calc R 1 . . H H13 0.1788 0.8979 0.5283 0.044 Uiso calc R 1 . . H H14 0.0128 0.9877 0.5712 0.046 Uiso calc R 1 . . H H15 -0.1156 1.0140 0.6768 0.052 Uiso calc R 1 . . H H16 -0.1447 0.9732 0.8035 0.056 Uiso calc R 1 . . H H17 -0.0160 0.8329 0.8851 0.052 Uiso calc R 1 . . H H18 0.1426 0.7340 0.8393 0.045 Uiso calc R 1 . . H H3 0.3368 0.8616 0.4435 0.079 Uiso calc R 1 . . H H31A 0.5087 0.9302 0.4168 0.053 Uiso calc R 1 . . H H31B 0.4288 1.0452 0.4357 0.053 Uiso calc R 1 . . H H32A 0.3463 1.0662 0.2984 0.075 Uiso calc R 1 . . H H32B 0.4311 0.9546 0.2808 0.075 Uiso calc R 1 . . H H32C 0.4947 1.0793 0.3166 0.075 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 N1 0.0325(7) 0.0346(7) 0.0276(6) 0.0034(5) 0.0087(5) 0.0004(5) C2 0.0434(9) 0.0331(8) 0.0308(8) 0.0040(7) 0.0085(6) 0.0039(6) C3 0.0445(9) 0.0376(9) 0.0317(8) -0.0017(7) 0.0141(7) 0.0026(7) N4 0.0341(7) 0.0344(7) 0.0311(6) 0.0002(5) 0.0119(5) -0.0018(5) C5 0.0334(8) 0.0382(9) 0.0390(9) -0.0030(6) 0.0127(7) 0.0007(7) C51 0.0469(10) 0.0466(10) 0.0527(11) -0.0106(8) 0.0152(8) 0.0039(8) C52 0.0399(9) 0.0511(10) 0.0443(9) 0.0053(8) 0.0169(7) 0.0001(8) C6 0.0357(8) 0.0360(8) 0.0385(9) -0.0010(6) 0.0070(7) -0.0031(7) C7 0.0314(8) 0.0383(9) 0.0343(8) 0.0030(6) 0.0059(6) -0.0020(7) C71 0.0463(10) 0.0466(10) 0.0340(8) 0.0035(8) 0.0036(7) -0.0038(7) O1 0.0469(7) 0.0525(7) 0.0414(6) 0.0206(6) 0.0177(5) 0.0117(6) O2 0.0492(7) 0.0488(7) 0.0388(6) 0.0102(5) 0.0207(5) 0.0083(5) C11 0.0318(8) 0.0282(7) 0.0360(8) 0.0019(6) 0.0069(6) 0.0010(6) C12 0.0305(8) 0.0294(8) 0.0336(8) 0.0004(6) 0.0074(6) -0.0015(6) C13 0.0391(9) 0.0384(9) 0.0324(8) 0.0031(7) 0.0079(7) 0.0017(7) C14 0.0370(8) 0.0384(9) 0.0389(9) 0.0072(7) 0.0047(7) 0.0039(7) C15 0.0368(9) 0.0424(9) 0.0507(10) 0.0091(7) 0.0106(7) 0.0021(8) C16 0.0395(9) 0.0513(10) 0.0539(11) 0.0066(8) 0.0206(8) -0.0022(9) C17 0.0424(9) 0.0467(10) 0.0446(9) -0.0014(8) 0.0187(8) -0.0007(8) C18 0.0373(8) 0.0374(9) 0.0397(9) -0.0010(7) 0.0117(7) 0.0028(7) C19 0.0294(7) 0.0299(7) 0.0373(8) -0.0020(6) 0.0086(6) -0.0010(6) C110 0.0311(8) 0.0339(8) 0.0398(8) 0.0004(6) 0.0079(6) -0.0029(7) C111 0.0351(8) 0.0317(8) 0.0366(8) 0.0012(6) 0.0103(7) -0.0016(7) O3 0.0558(8) 0.0567(8) 0.0439(7) -0.0062(6) 0.0052(6) 0.0125(6) C31 0.0484(10) 0.0435(10) 0.0400(9) 0.0004(8) 0.0058(7) -0.0043(8) C32 0.0579(11) 0.0538(11) 0.0409(9) -0.0116(9) 0.0165(8) -0.0085(8) 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 . 1.487(2) y N1 C7 3_666 1.501(2) y N1 H1A . 0.92 no N1 H1B . 0.92 no C2 C3 . 1.508(2) no C2 H2A . 0.99 no C2 H2B . 0.99 no N4 C3 . 1.465(2) y C3 H3A . 0.99 no C3 H3B . 0.99 no N4 C5 . 1.495(2) y N4 H4 . 0.92 no C5 C52 . 1.536(2) no C5 C6 . 1.539(2) no C5 C51 . 1.540(2) no C51 H51A . 0.98 no C51 H51B . 0.98 no C51 H51C . 0.98 no C52 H52A . 0.98 no C52 H52B . 0.98 no C52 H52C . 0.98 no C6 C7 . 1.526(2) no C6 H6A . 0.99 no C6 H6B . 0.99 no C7 C71 . 1.524(2) no C7 H7 . 1.00 no C71 H71A . 0.98 no C71 H71B . 0.98 no C71 H71C . 0.98 no O1 C111 . 1.2602(19) no O2 C111 . 1.2538(18) no C11 C12 . 1.370(2) no C11 C19 . 1.419(2) no C11 H11 . 0.95 no C12 C13 . 1.418(2) no C12 C111 . 1.515(2) no C13 C14 . 1.373(2) no C13 H13 . 0.95 no C14 C110 . 1.417(2) no C14 H14 . 0.95 no C15 C16 . 1.364(2) no C15 C110 . 1.419(2) no C15 H15 . 0.95 no C16 C17 . 1.409(2) no C16 H16 . 0.95 no C17 C18 . 1.368(2) no C17 H17 . 0.95 no C18 C19 . 1.423(2) no C18 H18 . 0.95 no C19 C110 . 1.421(2) no O3 C31 . 1.421(2) no O3 H3 . 0.84 no C31 C32 . 1.494(2) no C31 H31A . 0.99 no C31 H31B . 0.99 no C32 H32A . 0.98 no C32 H32B . 0.98 no C32 H32C . 0.98 no