data_2011847 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 480 _journal_page_last 482 _publ_section_title ; Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa: uncarine C and uncarine E ; loop_ _publ_author_name ' Muhammad, Ilias ' 'Khan, Ikhlas A. ' 'Fischer, Nikolaus H. ' 'Fronczek, Frank R.' _chemical_name_common isopteropodine _chemical_formula_moiety 'C21 H24 N2 O4 ' _chemical_formula_sum 'C21 H24 N2 O4' _chemical_formula_weight 368.42 _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9943(8) _cell_length_b 21.062(3) _cell_length_c 12.3039(15) _cell_angle_alpha 90 _cell_angle_beta 96.860(6) _cell_angle_gamma 90 _cell_volume 2828.7(5) _cell_formula_units_Z 6 _cell_measurement_temperature 120 _exptl_crystal_density_diffrn 1.298 _diffrn_ambient_temperature 120 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 O1A .9823(3) .24244(16) .4239(3) .0312(9) Uani d . 1 . . O O2A .5102(3) .40584(16) .7357(3) .0351(9) Uani d . 1 . . O O3A .6383(3) .44231(17) .3848(3) .0330(9) Uani d . 1 . . O O4A .5253(3) .51349(15) .4653(3) .0325(9) Uani d . 1 . . O N1A 1.1035(3) .30046(19) .5535(3) .0289(11) Uani d . 1 . . N H1NA 1.1601 .3126 .5130 .035 Uiso calc R 1 . . H N2A .7344(3) .23825(18) .6632(3) .0246(10) Uani d . 1 . . N C2A 1.0062(4) .2633(2) .5175(5) .0261(13) Uani d . 1 . . C C3A .7953(4) .2729(2) .5821(4) .0222(12) Uani d . 1 . . C H3A .7658 .2555 .5080 .027 Uiso calc R 1 . . H C5A .7790(4) .1731(2) .6534(4) .0324(13) Uani d . 1 . . C H5A1 .7341 .1514 .5894 .039 Uiso calc R 1 . . H H5A2 .7697 .1483 .7203 .039 Uiso calc R 1 . . H C6A .9155(4) .1816(2) .6385(4) .0283(13) Uani d . 1 . . C H6A1 .9374 .1547 .5777 .034 Uiso calc R 1 . . H H6A2 .9684 .1698 .7063 .034 Uiso calc R 1 . . H C7A .9309(4) .2528(2) .6121(4) .0235(12) Uani d . 1 . . C C8A 1.0015(4) .2898(2) .7027(4) .0255(13) Uani d . 1 . . C C9A .9833(4) .2982(3) .8110(4) .0344(14) Uani d . 1 . . C H9A .9140 .2804 .8391 .041 Uiso calc R 1 . . H C10A 1.0702(5) .3338(3) .8784(5) .0423(15) Uani d . 1 . . C H10A 1.0603 .3398 .9534 .051 Uiso calc R 1 . . H C11A 1.1700(5) .3602(3) .8367(5) .0380(15) Uani d . 1 . . C H11A 1.2268 .3846 .8837 .046 Uiso calc R 1 . . H C12A 1.1899(4) .3521(2) .7277(4) .0310(13) Uani d . 1 . . C H12A 1.2591 .3695 .6991 .037 Uiso calc R 1 . . H C13A 1.1020(4) .3171(2) .6641(4) .0269(13) Uani d . 1 . . C C14A .7642(4) .3432(2) .5827(4) .0248(12) Uani d . 1 . . C H14A .8059 .3658 .5271 .030 Uiso calc R 1 . . H H14B .7919 .3617 .6554 .030 Uiso calc R 1 . . H C15A .6228(4) .3502(2) .5561(4) .0237(12) Uani d . 1 . . C H15A .5986 .3331 .4808 .028 Uiso calc R 1 . . H C16A .5796(4) .4179(2) .5587(4) .0222(12) Uani d . 1 . . C C17A .5246(4) .4387(3) .6425(4) .0309(13) Uani d . 1 . . C H17A .4921 .4805 .6369 .037 Uiso calc R 1 . . H C18A .5073(4) .3097(3) .8343(4) .0376(14) Uani d . 1 . . C H18A .5031 .3385 .8964 .056 Uiso calc R 1 . . H H18B .5545 .2718 .8591 .056 Uiso calc R 1 . . H H18C .4243 .2972 .8040 .056 Uiso calc R 1 . . H C19A .5695(4) .3433(2) .7467(4) .0297(13) Uani d . 1 . . C H19A .6583 .3490 .7736 .036 Uiso calc R 1 . . H C20A .5577(4) .3109(2) .6362(4) .0224(12) Uani d . 1 . . C H20A .4686 .3106 .6077 .027 Uiso calc R 1 . . H C21A .6009(4) .2425(2) .6384(4) .0268(13) Uani d . 1 . . C H21A .5619 .2188 .6946 .032 Uiso calc R 1 . . H H21B .5752 .2225 .5665 .032 Uiso calc R 1 . . H C22A .5871(4) .4571(2) .4614(5) .0274(13) Uani d . 1 . . C C23A .5237(4) .5518(2) .3683(4) .0346(14) Uani d . 1 . . C H23A .6073 .5561 .3490 .052 Uiso calc R 1 . . H H23B .4909 .5939 .3819 .052 Uiso calc R 1 . . H H23C .4719 .5315 .3078 .052 Uiso calc R 1 . . H O1B .6194(3) .29109(16) .2775(3) .0310(9) Uani d . 1 . . O O2B .1452(3) .03740(17) .3765(3) .0396(10) Uani d . 1 . . O O3B .3279(3) .20947(17) .5859(3) .0351(9) Uani d . 1 . . O O4B .2100(3) .13731(16) .6582(3) .0352(9) Uani d . 1 . . O N1B .7486(3) .20499(19) .3081(3) .0274(10) Uani d . 1 . . N H1NB .8133 .2252 .3401 .033 Uiso calc R 1 . . H N2B .3560(3) .1505(2) .1553(3) .0306(11) Uani d . 1 . . N C2B .6403(4) .2338(3) .2699(4) .0279(13) Uani d . 1 . . C C3B .4278(4) .1855(2) .2464(4) .0273(13) Uani d . 1 . . C H3B .3997 .2307 .2440 .033 Uiso calc R 1 . . H C5B .3952(4) .1781(3) .0558(4) .0427(15) Uani d . 1 . . C H5B1 .3434 .2151 .0312 .051 Uiso calc R 1 . . H H5B2 .3895 .1463 -.0039 .051 Uiso calc R 1 . . H C6B .5286(4) .1987(3) .0873(4) .0315(13) Uani d . 1 . . C H6B1 .5385 .2446 .0739 .038 Uiso calc R 1 . . H H6B2 .5842 .1747 .0447 .038 Uiso calc R 1 . . H C7B .5563(4) .1833(2) .2118(4) .0240(12) Uani d . 1 . . C C8B .6292(4) .1231(2) .2350(4) .0230(12) Uani d . 1 . . C C9B .6040(4) .0615(2) .2078(4) .0280(13) Uani d . 1 . . C H9B .5269 .0500 .1696 .034 Uiso calc R 1 . . H C10B .6934(4) .0156(2) .2369(4) .0317(13) Uani d . 1 . . C H10B .6764 -.0277 .2191 .038 Uiso calc R 1 . . H C11B .8061(5) .0321(2) .2913(4) .0328(14) Uani d . 1 . . C H11B .8658 .0001 .3099 .039 Uiso calc R 1 . . H C12B .8337(4) .0952(2) .3195(4) .0307(14) Uani d . 1 . . C H12B .9109 .1070 .3573 .037 Uiso calc R 1 . . H C13B .7437(4) .1395(2) .2899(4) .0248(12) Uani d . 1 . . C C14B .4041(4) .1573(2) .3546(4) .0272(12) Uani d . 1 . . C H14C .4509 .1810 .4154 .033 Uiso calc R 1 . . H H14D .4317 .1125 .3589 .033 Uiso calc R 1 . . H C15B .2650(4) .1607(2) .3658(4) .0281(13) Uani d . 1 . . C H15B .2414 .2066 .3674 .034 Uiso calc R 1 . . H C16B .2319(4) .1300(2) .4691(4) .0283(13) Uani d . 1 . . C C17B .1742(4) .0741(3) .4652(4) .0325(14) Uani d . 1 . . C H17B .1513 .0585 .5323 .039 Uiso calc R 1 . . H C18B .1217(5) .0219(3) .1860(5) .0561(18) Uani d . 1 . . C H18D .1164 -.0227 .2077 .084 Uiso calc R 1 . . H H18E .1621 .0247 .1193 .084 Uiso calc R 1 . . H H18F .0391 .0399 .1720 .084 Uiso calc R 1 . . H C19B .1942(4) .0582(2) .2758(4) .0346(14) Uani d . 1 . . C H19B .2819 .0448 .2800 .041 Uiso calc R 1 . . H C20B .1883(4) .1298(3) .2678(4) .0322(14) Uani d . 1 . . C H20B .1011 .1422 .2717 .039 Uiso calc R 1 . . H C21B .2245(4) .1571(3) .1602(4) .0347(14) Uani d . 1 . . C H21C .1790 .1345 .0974 .042 Uiso calc R 1 . . H H21D .2016 .2025 .1545 .042 Uiso calc R 1 . . H C22B .2621(4) .1639(3) .5727(4) .0289(13) Uani d . 1 . . C C23B .2466(4) .1669(3) .7629(4) .0391(15) Uani d . 1 . . C H23D .3357 .1637 .7807 .059 Uiso calc R 1 . . H H23E .2064 .1454 .8196 .059 Uiso calc R 1 . . H H23F .2226 .2117 .7596 .059 Uiso calc R 1 . . H O1C 1.3072(3) .33869(17) .4440(3) .0348(9) Uani d . 1 . . O O2C .7472(3) .40391(17) .0221(3) .0347(9) Uani d . 1 . . O O3C .9602(3) .21591(16) .1487(3) .0381(10) Uani d . 1 . . O O4C .8220(3) .21659(16) -.0024(3) .0370(9) Uani d . 1 . . O N1C 1.4011(3) .36389(19) .2925(3) .0278(10) Uani d . 1 . . N H1NC 1.4620 .3366 .3022 .033 Uiso calc R 1 . . H N2C 1.0237(3) .45901(18) .3033(3) .0270(10) Uani d . 1 . . N C2C 1.3138(4) .3703(2) .3616(4) .0281(13) Uani d . 1 . . C C3C 1.0923(4) .3994(2) .3013(4) .0225(12) Uani d . 1 . . C H3C 1.0780 .3738 .3672 .027 Uiso calc R 1 . . H C5C 1.0820(4) .4919(3) .3996(4) .0358(14) Uani d . 1 . . C H5C1 1.0512 .4757 .4667 .043 Uiso calc R 1 . . H H5C2 1.0662 .5381 .3938 .043 Uiso calc R 1 . . H C6C 1.2186(4) .4779(2) .4015(4) .0312(14) Uani d . 1 . . C H6C1 1.2544 .4642 .4755 .037 Uiso calc R 1 . . H H6C2 1.2629 .5161 .3805 .037 Uiso calc R 1 . . H C7C 1.2264(4) .4238(2) .3170(4) .0238(12) Uani d . 1 . . C C8C 1.2771(4) .4428(2) .2134(4) .0242(12) Uani d . 1 . . C C9C 1.2432(4) .4879(2) .1348(4) .0319(13) Uani d . 1 . . C H9C 1.1734 .5138 .1402 .038 Uiso calc R 1 . . H C10C 1.3102(4) .4956(3) .0483(5) .0367(14) Uani d . 1 . . C H10C 1.2859 .5263 -.0066 .044 Uiso calc R 1 . . H C11C 1.4129(4) .4588(3) .0410(4) .0377(14) Uani d . 1 . . C H11C 1.4586 .4650 -.0189 .045 Uiso calc R 1 . . H C12C 1.4511(4) .4129(2) .1188(4) .0283(13) Uani d . 1 . . C H12C 1.5215 .3876 .1134 .034 Uiso calc R 1 . . H C13C 1.3822(4) .4061(2) .2039(4) .0231(12) Uani d . 1 . . C C14C 1.0493(4) .3612(2) .2003(4) .0266(13) Uani d . 1 . . C H14E 1.0968 .3213 .2001 .032 Uiso calc R 1 . . H H14F 1.0620 .3856 .1339 .032 Uiso calc R 1 . . H C15C .9116(4) .3459(2) .1997(4) .0243(12) Uani d . 1 . . C H15C .9025 .3174 .2634 .029 Uiso calc R 1 . . H C16C .8578(4) .3127(2) .0979(4) .0234(12) Uani d . 1 . . C C17C .7784(4) .3419(3) .0219(4) .0323(13) Uani d . 1 . . C H17C .7412 .3167 -.0369 .039 Uiso calc R 1 . . H C18C .7445(5) .5037(2) .1080(5) .0414(15) Uani d . 1 . . C H18G .7127 .5162 .0332 .062 Uiso calc R 1 . . H H18H .7975 .5375 .1420 .062 Uiso calc R 1 . . H H18I .6760 .4969 .1508 .062 Uiso calc R 1 . . H C19C .8171(4) .4433(2) .1050(4) .0320(13) Uani d . 1 . . C H19C .8988 .4532 .0811 .038 Uiso calc R 1 . . H C20C .8355(4) .4071(2) .2130(4) .0253(12) Uani d . 1 . . C H20C .7528 .3934 .2298 .030 Uiso calc R 1 . . H C21C .8925(4) .4462(2) .3096(4) .0271(12) Uani d . 1 . . C H21E .8481 .4870 .3114 .032 Uiso calc R 1 . . H H21F .8837 .4231 .3783 .032 Uiso calc R 1 . . H C22C .8863(4) .2453(2) .0870(4) .0279(13) Uani d . 1 . . C C23C .8493(5) .1506(3) -.0161(5) .0567(19) Uani d . 1 . . C H23G .9328 .1464 -.0356 .085 Uiso calc R 1 . . H H23H .7911 .1326 -.0746 .085 Uiso calc R 1 . . H H23I .8428 .1279 .0524 .085 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 O1A .0217(17) .039(2) .032(2) .0032(16) .0035(16) -.0040(19) O2A .039(2) .036(2) .032(2) .0118(18) .0106(17) .0059(19) O3A .0325(19) .036(2) .032(2) .0016(17) .0105(18) .001(2) O4A .0322(19) .026(2) .040(2) .0071(17) .0066(17) .0057(19) N1A .021(2) .032(3) .036(3) -.008(2) .0076(19) .003(2) N2A .019(2) .027(3) .028(3) .0024(19) .0055(18) .005(2) C2A .021(3) .026(3) .030(4) .002(2) -.001(2) .003(3) C3A .018(2) .024(3) .025(3) .002(2) .004(2) .002(2) C5A .027(3) .026(3) .044(4) -.001(2) .004(2) .000(3) C6A .024(2) .023(3) .038(3) .007(2) .005(2) .004(3) C7A .014(2) .027(3) .029(3) .001(2) .002(2) -.002(3) C8A .022(3) .024(3) .030(3) .001(2) .001(2) .007(3) C9A .031(3) .043(4) .029(4) .002(3) .003(2) .002(3) C10A .038(3) .056(4) .032(4) -.005(3) .000(3) -.002(3) C11A .033(3) .041(4) .039(4) -.010(3) -.001(3) -.008(3) C12A .029(3) .030(3) .033(4) .003(2) .003(3) -.003(3) C13A .029(3) .029(3) .023(3) -.001(2) .002(2) .000(3) C14A .016(2) .028(3) .030(3) -.002(2) .000(2) -.003(3) C15A .015(2) .032(3) .024(3) -.003(2) .003(2) -.003(3) C16A .021(3) .023(3) .023(3) .001(2) .003(2) -.004(3) C17A .028(3) .027(3) .037(4) .005(2) .002(3) .001(3) C18A .030(3) .055(4) .029(3) .005(3) .005(2) .002(3) C19A .025(3) .034(3) .031(3) .007(2) .004(2) .006(3) C20A .011(2) .031(3) .025(3) -.003(2) .001(2) -.002(3) C21A .014(2) .038(3) .029(3) -.003(2) .006(2) .007(3) C22A .025(3) .024(3) .031(4) -.003(2) -.004(3) -.006(3) C23A .034(3) .032(3) .038(4) -.002(3) .001(3) .004(3) O1B .0295(19) .022(2) .043(2) -.0027(16) .0102(17) -.0004(18) O2B .035(2) .043(2) .041(3) -.0125(18) .0052(19) -.002(2) O3B .0296(19) .034(2) .042(2) -.0048(18) .0025(17) .0013(19) O4B .0371(19) .040(2) .029(2) -.0025(17) .0074(18) .0038(19) N1B .021(2) .025(3) .037(3) -.0034(19) .0031(19) .000(2) N2B .018(2) .049(3) .024(3) -.0038(19) .0018(19) .003(2) C2B .023(3) .034(4) .028(3) .003(2) .008(2) .003(3) C3B .023(3) .029(3) .030(3) .001(2) .004(2) -.001(3) C5B .034(3) .064(4) .032(4) -.008(3) .007(3) .008(3) C6B .022(3) .046(4) .027(3) .002(2) .005(2) .007(3) C7B .013(2) .029(3) .030(3) .000(2) .001(2) .001(3) C8B .024(3) .026(3) .020(3) -.004(2) .009(2) -.005(2) C9B .021(3) .039(4) .024(3) -.005(3) .003(2) -.008(3) C10B .031(3) .029(3) .037(4) .000(3) .013(3) -.003(3) C11B .035(3) .032(4) .031(3) .007(3) .004(3) .006(3) C12B .023(3) .038(4) .031(3) -.001(3) -.002(2) .005(3) C13B .020(3) .027(3) .027(3) -.002(2) .003(2) .000(3) C14B .022(2) .032(3) .028(3) .000(2) .004(2) -.001(3) C15B .021(2) .033(3) .031(3) .003(2) .007(2) .008(3) C16B .020(3) .030(3) .035(4) -.004(2) .005(2) .008(3) C17B .031(3) .042(4) .024(3) .005(3) .001(3) .002(3) C18B .058(4) .068(5) .043(4) -.027(4) .007(3) -.012(4) C19B .026(3) .042(4) .036(4) -.010(3) .007(3) -.003(3) C20B .020(2) .044(4) .032(3) -.005(3) .001(2) .003(3) C21B .016(2) .057(4) .031(3) -.001(3) .001(2) .003(3) C22B .022(3) .033(4) .032(4) .014(3) .006(3) .009(3) C23B .044(3) .042(4) .032(4) .009(3) .004(3) .001(3) O1C .0231(18) .043(2) .039(2) -.0007(17) .0047(17) .011(2) O2C .0325(19) .036(2) .034(2) .0034(18) -.0028(17) -.0011(19) O3C .038(2) .030(2) .044(3) .0054(18) -.0041(18) -.0004(19) O4C .044(2) .030(2) .037(2) -.0094(18) .0024(18) -.0092(18) N1C .020(2) .028(3) .036(3) .0004(19) .005(2) .007(2) N2C .023(2) .026(3) .032(3) .0011(19) .0040(19) -.009(2) C2C .023(3) .034(3) .026(3) -.004(2) .000(3) .006(3) C3C .025(3) .023(3) .021(3) .003(2) .007(2) -.001(2) C5C .028(3) .046(4) .035(3) -.004(3) .008(3) -.017(3) C6C .019(3) .040(4) .036(4) .001(2) .007(2) -.014(3) C7C .018(2) .026(3) .028(3) -.006(2) .005(2) -.007(3) C8C .026(3) .018(3) .029(3) -.006(2) .008(2) -.006(3) C9C .026(3) .026(3) .044(4) -.003(2) .005(3) .002(3) C10C .034(3) .035(4) .042(4) .007(3) .008(3) .010(3) C11C .035(3) .047(4) .032(3) .000(3) .010(3) -.003(3) C12C .030(3) .021(3) .033(3) .005(2) .003(3) -.002(3) C13C .019(3) .028(3) .023(3) -.005(2) .001(2) -.002(3) C14C .019(2) .028(3) .032(3) -.004(2) .003(2) -.004(2) C15C .022(2) .024(3) .027(3) .002(2) .003(2) -.003(2) C16C .022(3) .022(3) .027(3) -.002(2) .006(2) -.002(3) C17C .031(3) .035(3) .031(3) -.001(3) .002(3) -.003(3) C18C .044(3) .026(3) .053(4) .010(3) .001(3) .002(3) C19C .028(3) .029(3) .039(4) -.006(3) .004(2) .002(3) C20C .018(2) .031(3) .027(3) -.004(2) .006(2) -.001(3) C21C .020(2) .032(3) .030(3) -.006(2) .005(2) -.003(3) C22C .027(3) .031(3) .028(3) -.007(3) .016(3) -.008(3) C23C .060(4) .031(4) .078(5) -.008(3) .003(3) -.024(3) 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 O1A C2A . 1.231(5) ? O2A C17A . 1.365(6) ? O2A C19A . 1.470(6) ? O3A C22A . 1.196(6) ? O4A C22A . 1.372(6) ? O4A C23A . 1.439(6) ? N1A C2A . 1.356(6) ? N1A C13A . 1.407(6) ? N1A H1NA . .8800 ? N2A C3A . 1.461(6) ? N2A C21A . 1.467(5) ? N2A C5A . 1.466(6) ? C2A C7A . 1.523(7) ? C3A C14A . 1.519(6) ? C3A C7A . 1.552(6) ? C3A H3A . 1.0000 ? C5A C6A . 1.544(6) ? C5A H5A1 . .9900 ? C5A H5A2 . .9900 ? C6A C7A . 1.548(6) ? C6A H6A1 . .9900 ? C6A H6A2 . .9900 ? C7A C8A . 1.499(6) ? C8A C13A . 1.378(6) ? C8A C9A . 1.382(6) ? C9A C10A . 1.405(7) ? C9A H9A . .9500 ? C10A C11A . 1.382(7) ? C10A H10A . .9500 ? C11A C12A . 1.394(7) ? C11A H11A . .9500 ? C12A C13A . 1.382(6) ? C12A H12A . .9500 ? C14A C15A . 1.557(5) ? C14A H14A . .9900 ? C14A H14B . .9900 ? C15A C16A . 1.507(7) ? C15A C20A . 1.528(6) ? C15A H15A . 1.0000 ? C16A C17A . 1.329(6) ? C16A C22A . 1.464(7) ? C17A H17A . .9500 ? C18A C19A . 1.517(7) ? C18A H18A . .9800 ? C18A H18B . .9800 ? C18A H18C . .9800 ? C19A C20A . 1.513(6) ? C19A H19A . 1.0000 ? C20A C21A . 1.516(7) ? C20A H20A . 1.0000 ? C21A H21A . .9900 ? C21A H21B . .9900 ? C23A H23A . .9800 ? C23A H23B . .9800 ? C23A H23C . .9800 ? O1B C2B . 1.234(6) ? O2B C17B . 1.344(6) ? O2B C19B . 1.475(6) ? O3B C22B . 1.201(6) ? O4B C22B . 1.376(6) ? O4B C23B . 1.445(5) ? N1B C2B . 1.369(6) ? N1B C13B . 1.398(6) ? N1B H1NB . .8800 ? N2B C21B . 1.461(5) ? N2B C5B . 1.466(6) ? N2B C3B . 1.487(6) ? C2B C7B . 1.528(6) ? C3B C14B . 1.509(6) ? C3B C7B . 1.524(6) ? C3B H3B . 1.0000 ? C5B C6B . 1.535(6) ? C5B H5B1 . .9900 ? C5B H5B2 . .9900 ? C6B C7B . 1.559(6) ? C6B H6B1 . .9900 ? C6B H6B2 . .9900 ? C7B C8B . 1.509(6) ? C8B C9B . 1.359(6) ? C8B C13B . 1.399(6) ? C9B C10B . 1.395(6) ? C9B H9B . .9500 ? C10B C11B . 1.381(7) ? C10B H10B . .9500 ? C11B C12B . 1.398(7) ? C11B H11B . .9500 ? C12B C13B . 1.376(6) ? C12B H12B . .9500 ? C14B C15B . 1.554(6) ? C14B H14C . .9900 ? C14B H14D . .9900 ? C15B C16B . 1.510(6) ? C15B C20B . 1.531(6) ? C15B H15B . 1.0000 ? C16B C17B . 1.336(7) ? C16B C22B . 1.463(7) ? C17B H17B . .9500 ? C18B C19B . 1.493(7) ? C18B H18D . .9800 ? C18B H18E . .9800 ? C18B H18F . .9800 ? C19B C20B . 1.511(7) ? C19B H19B . 1.0000 ? C20B C21B . 1.539(6) ? C20B H20B . 1.0000 ? C21B H21C . .9900 ? C21B H21D . .9900 ? C23B H23D . .9800 ? C23B H23E . .9800 ? C23B H23F . .9800 ? O1C C2C . 1.222(6) ? O2C C17C . 1.349(6) ? O2C C19C . 1.459(5) ? O3C C22C . 1.213(5) ? O4C C22C . 1.374(5) ? O4C C23C . 1.436(6) ? N1C C2C . 1.362(6) ? N1C C13C . 1.402(6) ? N1C H1NC . .8800 ? N2C C5C . 1.453(6) ? N2C C3C . 1.467(5) ? N2C C21C . 1.479(5) ? C2C C7C . 1.539(6) ? C3C C14C . 1.508(6) ? C3C C7C . 1.552(6) ? C3C H3C . 1.0000 ? C5C C6C . 1.528(6) ? C5C H5C1 . .9900 ? C5C H5C2 . .9900 ? C6C C7C . 1.553(6) ? C6C H6C1 . .9900 ? C6C H6C2 . .9900 ? C7C C8C . 1.504(7) ? C8C C9C . 1.376(6) ? C8C C13C . 1.407(6) ? C9C C10C . 1.374(7) ? C9C H9C . .9500 ? C10C C11C . 1.381(7) ? C10C H10C . .9500 ? C11C C12C . 1.389(7) ? C11C H11C . .9500 ? C12C C13C . 1.371(6) ? C12C H12C . .9500 ? C14C C15C . 1.547(6) ? C14C H14E . .9900 ? C14C H14F . .9900 ? C15C C16C . 1.493(6) ? C15C C20C . 1.556(6) ? C15C H15C . 1.0000 ? C16C C17C . 1.349(6) ? C16C C22C . 1.463(7) ? C17C H17C . .9500 ? C18C C19C . 1.506(7) ? C18C H18G . .9800 ? C18C H18H . .9800 ? C18C H18I . .9800 ? C19C C20C . 1.524(6) ? C19C H19C . 1.0000 ? C20C C21C . 1.517(6) ? C20C H20C . 1.0000 ? C21C H21E . .9900 ? C21C H21F . .9900 ? C23C H23G . .9800 ? C23C H23H . .9800 ? C23C H23I . .9800 ?