data_2011713 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 88 _journal_page_last 91 _publ_section_title ; The hydrogen-bonded adduct 3,6,9,16,19,22-hexa-azatricyclo[22.2.2.2^11,14^]triaconta- 1(26),11(29),12,14(30),24,27-hexaene--3,5-dinitrobenzoic acid--methanol (1/4/2) contains seven-component supramolecular aggregates ; loop_ _publ_author_name 'Burchell, Colin J.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _chemical_formula_moiety 'C24 H42 N6 4+, 4C7 H3 N2 O6 - , 2C H4 O' _chemical_formula_sum 'C54 H62 N14 O26' _chemical_formula_weight 1323.18 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.6342(7) _cell_length_b 11.7501(2) _cell_length_c 21.4967(7) _cell_angle_alpha 90 _cell_angle_beta 102.3970(10) _cell_angle_gamma 90 _cell_volume 6077.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.446 _diffrn_ambient_temperature 150(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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N8 .17482(5) .36466(11) -.19969(6) .0214(3) Uani d . 1 . . N N11 .08358(6) .44525(12) -.15244(6) .0250(3) Uani d . 1 . . N N14 .09545(5) .37158(11) -.01941(6) .0203(3) Uani d . 1 . . N C1 .35895(7) .18968(15) -.09224(7) .0261(3) Uani d . 1 . . C C2 .35723(7) .30757(15) -.09678(9) .0331(4) Uani d . 1 . . C C3 .31457(7) .36108(15) -.13908(9) .0319(4) Uani d . 1 . . C C4 .27285(7) .29795(14) -.17799(8) .0257(3) Uani d . 1 . . C C5 .27454(7) .18024(15) -.17328(8) .0298(4) Uani d . 1 . . C C6 .31725(7) .12662(15) -.13065(8) .0292(4) Uani d . 1 . . C C7 .22699(7) .35751(16) -.22419(8) .0295(4) Uani d . 1 . . C C9 .13213(7) .43888(14) -.24003(8) .0252(3) Uani d . 1 . . C C10 .07729(7) .42458(15) -.22036(8) .0266(3) Uani d . 1 . . C C12 .03673(6) .40401(14) -.12788(8) .0245(3) Uani d . 1 . . C C13 .04456(6) .42690(13) -.05763(7) .0230(3) Uani d . 1 . . C C15 .09231(7) .36750(16) .04927(8) .0290(4) Uani d . 1 . . C O21 .21455(5) .50836(11) -.10152(6) .0369(3) Uani d . 1 . . O O22 .18626(5) .50095(10) -.00891(6) .0324(3) Uani d . 1 . . O O23 .30218(7) .67360(18) .17860(7) .0656(5) Uani d . 1 . . O O24 .37433(6) .77274(12) .17179(7) .0466(4) Uani d . 1 . . O O25 .41779(6) .83679(13) -.03275(8) .0520(4) Uani d . 1 . . O O26 .35892(8) .78649(18) -.11686(8) .0741(6) Uani d . 1 . . O N23 .33431(7) .71275(14) .14849(8) .0368(4) Uani d . 1 . . N N25 .37604(7) .78653(13) -.05973(9) .0382(4) Uani d . 1 . . N C21 .26814(6) .60204(13) -.01244(8) .0221(3) Uani d . 1 . . C C22 .27982(7) .61929(13) .05279(8) .0243(3) Uani d . 1 . . C C23 .32428(7) .68868(14) .08004(8) .0259(3) Uani d . 1 . . C C24 .35743(7) .74178(14) .04491(9) .0273(4) Uani d . 1 . . C C25 .34411(7) .72352(14) -.02010(8) .0263(3) Uani d . 1 . . C C26 .30075(7) .65473(13) -.04950(8) .0245(3) Uani d . 1 . . C C27 .21849(7) .52967(13) -.04411(8) .0250(3) Uani d . 1 . . C O51 .13197(6) .17955(13) -.07721(8) .0501(4) Uani d . 1 . . O C52 .18950(8) .18341(17) -.05248(10) .0382(4) Uani d . 1 . . C O31 .109(3) .026(5) -.1756(11) .046(3) Uani d PD .50 A -1 O O32 .125(3) .164(4) -.242(2) .044(3) Uani d PD .50 A -1 O O33 -.013(2) .176(2) -.448(2) .042(4) Uani d PD .50 A -1 O O34 -.0591(16) .024(3) -.4835(15) .041(4) Uani d PD .50 A -1 O O35 -.0132(15) -.331(2) -.3740(12) .0327(9) Uani d PD .50 A -1 O O36 .06511(12) -.3411(2) -.30487(13) .0400(4) Uani d PD .50 A -1 O N33 -.0261(8) .0766(17) -.4429(7) .0287(19) Uani d PD .50 A -1 N N35 .02760(14) -.2873(3) -.33845(17) .0262(6) Uani d PD .50 A -1 N C31 .0680(3) .0100(5) -.2860(4) .0299(4) Uani d PGD .50 A -1 C C32 .0360(3) .0721(4) -.3357(5) .0201(8) Uani d PGD .50 A -1 C C33 .0014(3) .0161(7) -.3859(4) .0187(9) Uani d PGD .50 A -1 C C34 -.0012(2) -.1021(7) -.3865(3) .0295(4) Uani d PGD .50 A -1 C C35 .0308(2) -.1642(4) -.3369(3) .0216(8) Uani d PGD .50 A -1 C C36 .0654(2) -.1082(5) -.2866(3) .0245(9) Uani d PGD .50 A -1 C C37 .1040(12) .072(2) -.2289(10) .0325(13) Uani d PD .50 A -1 C O41 .106(3) .032(5) -.1736(11) .046(3) Uani d PD .50 B -2 O O42 .121(3) .170(4) -.240(2) .044(3) Uani d PD .50 B -2 O O43 -.007(2) .176(2) -.453(2) .042(4) Uani d PD .50 B -2 O O44 -.0521(16) .023(3) -.4874(15) .041(4) Uani d PD .50 B -2 O O45 -.0109(15) -.327(2) -.3744(12) .0327(9) Uani d PD .50 B -2 O O46 .01862(12) -.3199(2) -.27186(13) .0400(4) Uani d PD .50 B -2 O N43 -.0176(8) .0746(17) -.4481(7) .0287(19) Uani d PD .50 B -2 N N45 .00775(14) -.2750(3) -.32428(17) .0262(6) Uani d PD .50 B -2 N C41 .0655(3) .0152(6) -.2840(4) .0299(4) Uani d PGD .50 B -2 C C42 .0458(3) .0714(5) -.3414(5) .0201(8) Uani d PGD .50 B -2 C C43 .0119(3) .0145(7) -.3918(4) .0187(9) Uani d PGD .50 B -2 C C44 -.0024(2) -.0985(7) -.3849(3) .0295(4) Uani d PGD .50 B -2 C C45 .0172(2) -.1547(4) -.3276(3) .0216(8) Uani d PGD .50 B -2 C C46 .0512(2) -.0978(5) -.2771(3) .0245(9) Uani d PGD .50 B -2 C C47 .1010(12) .078(2) -.2269(10) .0325(13) Uani d PD .50 B -2 C H8A .1604 .2927 -.1983 .026 Uiso calc R 1 . . H H8B .1830 .3929 -.1588 .026 Uiso calc R 1 . . H H11 .0875 .5222 -.1449 .030 Uiso calc R 1 . . H H14A .1264 .4120 -.0238 .024 Uiso calc R 1 . . H H14B .0985 .2989 -.0342 .024 Uiso calc R 1 . . H H2 .3855 .3518 -.0707 .040 Uiso calc R 1 . . H H3 .3138 .4418 -.1416 .038 Uiso calc R 1 . . H H5 .2463 .1360 -.1994 .036 Uiso calc R 1 . . H H6 .3179 .0459 -.1278 .035 Uiso calc R 1 . . H H7A .2393 .4353 -.2322 .035 Uiso calc R 1 . . H H7B .2194 .3159 -.2652 .035 Uiso calc R 1 . . H H9A .1279 .4179 -.2854 .030 Uiso calc R 1 . . H H9B .1441 .5194 -.2349 .030 Uiso calc R 1 . . H H10A .0498 .4786 -.2446 .032 Uiso calc R 1 . . H H10B .0632 .3464 -.2306 .032 Uiso calc R 1 . . H H12A .0324 .3211 -.1357 .029 Uiso calc R 1 . . H H12B .0023 .4419 -.1508 .029 Uiso calc R 1 . . H H13A .0471 .5101 -.0503 .028 Uiso calc R 1 . . H H13B .0116 .3987 -.0428 .028 Uiso calc R 1 . . H H15A .0579 .3268 .0529 .035 Uiso calc R 1 . . H H15B .0894 .4463 .0645 .035 Uiso calc R 1 . . H H22 .2577 .5842 .0786 .029 Uiso calc R 1 . . H H24 .3879 .7885 .0643 .033 Uiso calc R 1 . . H H26 .2933 .6435 -.0943 .029 Uiso calc R 1 . . H H51 .1253 .1371 -.1094 .075 Uiso calc R 1 . . H H52A .2017 .2629 -.0477 .057 Uiso calc R 1 . . H H52B .2089 .1443 -.0816 .057 Uiso calc R 1 . . H H52C .1981 .1457 -.0108 .057 Uiso calc R 1 . . H H32 .0378 .1529 -.3353 .024 Uiso calc PR .50 A -1 H H34 -.0249 -.1404 -.4209 .035 Uiso calc PR .50 A -1 H H36 .0873 -.1507 -.2527 .029 Uiso calc PR .50 A -1 H H42 .0556 .1486 -.3461 .024 Uiso calc PR .50 B -2 H H44 -.0257 -.1374 -.4193 .035 Uiso calc PR .50 B -2 H H46 .0646 -.1362 -.2380 .029 Uiso calc PR .50 B -2 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 N8 .0219(6) .0219(7) .0190(6) -.0018(5) .0014(5) -.0007(5) N11 .0248(7) .0266(7) .0230(7) -.0052(5) .0037(5) -.0028(5) N14 .0182(6) .0211(6) .0215(6) -.0012(5) .0036(5) .0003(5) C1 .0245(8) .0354(9) .0182(8) .0038(7) .0039(6) .0011(6) C2 .0276(9) .0343(10) .0326(10) -.0016(7) -.0040(7) -.0040(7) C3 .0302(9) .0294(9) .0339(10) .0004(7) .0020(7) -.0006(7) C4 .0224(8) .0339(9) .0215(8) .0035(6) .0065(6) .0027(6) C5 .0264(8) .0352(10) .0255(9) -.0035(7) .0003(7) -.0033(7) C6 .0311(9) .0286(9) .0270(9) .0004(7) .0043(7) .0005(7) C7 .0250(8) .0402(10) .0231(8) .0031(7) .0045(7) .0046(7) C9 .0262(8) .0270(8) .0206(8) .0037(6) .0011(6) .0038(6) C10 .0241(8) .0311(9) .0222(8) .0015(6) -.0007(6) -.0006(6) C12 .0207(7) .0253(8) .0252(8) -.0016(6) -.0002(6) .0017(6) C13 .0189(7) .0240(8) .0250(8) .0016(6) .0022(6) .0034(6) C15 .0245(8) .0405(10) .0220(8) .0061(7) .0054(7) .0021(7) O21 .0329(7) .0451(8) .0320(7) -.0130(6) .0058(6) -.0147(6) O22 .0266(6) .0358(7) .0342(7) -.0118(5) .0053(5) -.0014(5) O23 .0502(10) .1188(15) .0305(8) -.0182(10) .0147(7) -.0186(9) O24 .0514(9) .0411(8) .0365(8) -.0043(7) -.0145(7) -.0078(6) O25 .0381(8) .0525(9) .0723(11) -.0243(7) .0270(8) -.0210(8) O26 .0772(13) .1034(15) .0424(10) -.0467(11) .0142(9) .0126(9) N23 .0318(8) .0458(9) .0294(8) .0033(7) -.0009(7) -.0091(7) N25 .0337(8) .0343(9) .0507(11) -.0116(7) .0178(8) -.0046(7) C21 .0200(7) .0191(7) .0265(8) .0005(6) .0035(6) -.0016(6) C22 .0227(8) .0238(8) .0262(8) -.0002(6) .0047(6) -.0005(6) C23 .0233(8) .0286(9) .0238(8) .0030(6) .0003(6) -.0056(6) C24 .0191(7) .0249(8) .0361(9) -.0008(6) .0019(7) -.0080(7) C25 .0221(8) .0235(8) .0344(9) -.0023(6) .0087(7) -.0032(7) C26 .0244(8) .0226(8) .0265(8) -.0002(6) .0056(6) -.0033(6) C27 .0210(7) .0205(8) .0315(9) -.0022(6) .0010(7) -.0031(6) O51 .0355(8) .0545(9) .0554(10) .0090(6) -.0009(7) -.0278(7) C52 .0343(10) .0400(11) .0400(11) .0060(8) .0075(8) -.0016(8) O31 .062(6) .037(4) .0313(12) -.015(4) -.004(2) -.0024(18) O32 .056(6) .029(3) .043(2) -.017(4) -.001(3) -.005(2) O33 .061(8) .0232(7) .040(4) .007(2) .007(5) .0064(15) O34 .043(7) .0387(12) .033(3) .009(4) -.008(4) -.0009(19) O35 .038(2) .0250(14) .0333(7) -.0084(11) .0036(10) -.0072(9) O36 .0535(12) .0242(9) .0373(11) -.0017(8) -.0015(8) .0064(8) N33 .033(5) .0257(10) .027(2) .011(2) .007(2) .0012(15) N35 .0334(19) .0210(10) .0239(14) -.0011(12) .0055(10) -.0010(9) C31 .0340(10) .0238(10) .0291(10) -.0061(8) .0006(8) -.0025(7) C32 .018(3) .0192(8) .0272(17) -.0001(9) .0146(15) -.0023(7) C33 .013(3) .0241(9) .0227(15) .0056(13) .0122(13) .0004(9) C34 .0322(9) .0265(9) .0265(9) -.0043(7) -.0008(7) -.0006(7) C35 .022(2) .0189(11) .0248(19) -.0018(14) .0079(14) -.0034(10) C36 .024(2) .0257(14) .0233(18) -.0016(16) .0050(14) -.0006(12) C37 .036(2) .025(2) .0337(13) -.0042(18) -.0004(14) -.0061(10) O41 .062(6) .037(4) .0313(12) -.015(4) -.004(2) -.0024(18) O42 .056(6) .029(3) .043(2) -.017(4) -.001(3) -.005(2) O43 .061(8) .0232(7) .040(4) .007(2) .007(5) .0064(15) O44 .043(7) .0387(12) .033(3) .009(4) -.008(4) -.0009(19) O45 .038(2) .0250(14) .0333(7) -.0084(11) .0036(10) -.0072(9) O46 .0535(12) .0242(9) .0373(11) -.0017(8) -.0015(8) .0064(8) N43 .033(5) .0257(10) .027(2) .011(2) .007(2) .0012(15) N45 .0334(19) .0210(10) .0239(14) -.0011(12) .0055(10) -.0010(9) C41 .0340(10) .0238(10) .0291(10) -.0061(8) .0006(8) -.0025(7) C42 .018(3) .0192(8) .0272(17) -.0001(9) .0146(15) -.0023(7) C43 .013(3) .0241(9) .0227(15) .0056(13) .0122(13) .0004(9) C44 .0322(9) .0265(9) .0265(9) -.0043(7) -.0008(7) -.0006(7) C45 .022(2) .0189(11) .0248(19) -.0018(14) .0079(14) -.0034(10) C46 .024(2) .0257(14) .0233(18) -.0016(16) .0050(14) -.0006(12) C47 .036(2) .025(2) .0337(13) -.0042(18) -.0004(14) -.0061(10) 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 N8 C7 . 1.492(2) y N8 C9 . 1.492(2) y N8 H8A . .92 no N8 H8B . .92 no N11 C10 . 1.455(2) y N11 C12 . 1.452(2) y N11 H11 . .92 no N14 C13 . 1.492(2) y N14 C15 . 1.496(2) y N14 H14A . .92 no N14 H14B . .92 no C1 C6 . 1.386(2) no C1 C2 . 1.389(3) no C1 C15 7 1.507(2) no C2 C3 . 1.384(2) no C2 H2 . .95 no C3 C4 . 1.392(2) no C3 H3 . .95 no C4 C5 . 1.387(2) no C4 C7 . 1.507(2) no C5 C6 . 1.389(2) no C5 H5 . .95 no C6 H6 . .95 no C7 H7A . .99 no C7 H7B . .99 no C9 C10 . 1.509(2) no C9 H9A . .99 no C9 H9B . .99 no C10 H10A . .99 no C10 H10B . .99 no C12 C13 . 1.505(2) no C12 H12A . .99 no C12 H12B . .99 no C13 H13A . .99 no C13 H13B . .99 no C15 C1 7 1.507(2) no C15 H15A . .99 no C15 H15B . .99 no O21 C27 . 1.242(2) y O22 C27 . 1.255(2) y O23 N23 . 1.215(2) y O24 N23 . 1.228(2) y O25 N25 . 1.219(2) y O26 N25 . 1.210(2) y N23 C23 . 1.466(2) y N25 C25 . 1.476(2) y C21 C22 . 1.384(2) no C21 C26 . 1.392(2) no C21 C27 . 1.525(2) no C22 C23 . 1.390(2) no C22 H22 . .95 no C23 C24 . 1.375(2) no C24 C25 . 1.382(2) no C24 H24 . .95 no C25 C26 . 1.380(2) no C26 H26 . .95 no O51 C52 . 1.404(2) y O51 H51 . .84 no C52 H52A . .98 no C52 H52B . .98 no C52 H52C . .98 no O31 C37 . 1.248(10) no O32 C37 . 1.248(10) no O33 N33 . 1.229(10) no O34 N33 . 1.223(10) no O35 N35 . 1.235(15) no O36 N35 . 1.220(4) no N33 C33 . 1.451(8) no N35 C35 . 1.448(6) no C31 C32 . 1.39 no C31 C36 . 1.39 no C31 C37 . 1.537(9) no C32 C33 . 1.39 no C32 H32 . .95 no C33 C34 . 1.39 no C34 C35 . 1.39 no C34 H34 . .95 no C35 C36 . 1.39 no C36 H36 . .95 no O41 C47 . 1.248(10) no O42 C47 . 1.248(10) no O43 N43 . 1.227(10) no O44 N43 . 1.225(10) no O45 N45 . 1.235(15) no O46 N45 . 1.221(4) no N43 C43 . 1.453(8) no N45 C45 . 1.438(6) no C41 C42 . 1.39 no C41 C46 . 1.39 no C41 C47 . 1.537(9) no C42 C43 . 1.39 no C42 H42 . .95 no C43 C44 . 1.39 no C44 C45 . 1.39 no C44 H44 . .95 no C45 C46 . 1.39 no C46 H46 . .95 no