#------------------------------------------------------------------------------ #$Date: 2016-02-20 01:53:41 +0100 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100544.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2100544 loop_ _publ_author_name 'V. Ferretti' 'L. Pretto' 'M. A. Tabrizi' 'P. Gilli' _publ_section_title ; Role of strong intramolecular N---H···N hydrogen bonds in determining the conformation of adenosine-receptor antagonists ; _journal_coeditor_code DE5026 _journal_date_accepted 2006-04-18 _journal_date_recd_electronic 2006-01-20 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 634 _journal_page_last 641 _journal_paper_category FA _journal_paper_doi 10.1107/S0108768106013966 _journal_volume 62 _journal_year 2006 _chemical_formula_moiety '(C22 H22 N8 O3), 0.5(C4 H8 O2)' _chemical_formula_sum 'C26 H30 N8 O5' _chemical_formula_weight 490.53 _chemical_name_systematic ; N-[8-butyl-2-(2-furyl)-8H-pyrazolo[4,3-e][1,2,4] triazolo[1,5-c]pyrimidin-5-yl]N-(2-methoxyphenyl)urea 0.5 dioxane solvate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 72.8670(7) _cell_angle_beta 71.3280(7) _cell_angle_gamma 70.6350(9) _cell_formula_units_Z 4 _cell_length_a 12.6218(2) _cell_length_b 14.0932(3) _cell_length_c 15.6948(4) _cell_measurement_reflns_used 15610 _cell_measurement_temperature 295 _cell_measurement_theta_max 27.0 _cell_measurement_theta_min 2.0 _cell_volume 2439.15(9) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPIII(Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WINGX (Farrugia, 1999) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 295 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15610 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.96 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1032 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.272 _refine_diff_density_min -0.199 _refine_ls_extinction_coef 0.054(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 889 _refine_ls_number_reflns 10558 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0609 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+0.5314P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1480 _refine_ls_wR_factor_ref 0.1829 _reflns_number_gt 6467 _reflns_number_total 10558 _reflns_threshold_expression I>2sigma(I) _cod_data_source_file de5026.cif _cod_data_source_block compound3 _cod_original_cell_volume 2439.16(9) _cod_database_code 2100544 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _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 O O1A 1.28893(15) 0.26617(15) -0.09746(13) 0.0801(5) Uani d . 1 O O2A 0.83391(15) 0.15403(14) 0.24399(11) 0.0783(5) Uani d . 1 O O3A 1.29417(16) 0.18973(14) -0.37575(11) 0.0766(5) Uani d . 1 N N1A 1.27861(17) 0.20955(15) -0.21577(13) 0.0633(5) Uani d . 1 N N2A 1.13523(17) 0.20846(16) -0.08019(14) 0.0652(5) Uani d . 1 N N3A 1.07998(16) 0.15832(14) -0.18595(12) 0.0595(5) Uani d . 1 N N4A 1.00524(17) 0.10412(14) -0.28009(13) 0.0649(5) Uani d . 1 N N5A 0.91157(18) 0.06644(15) -0.26095(13) 0.0659(5) Uani d . 1 N N6A 0.81605(16) 0.09127(15) 0.03984(12) 0.0637(5) Uani d . 1 N N7A 0.96959(15) 0.15020(13) -0.03305(12) 0.0563(4) Uani d . 1 N N8A 0.94590(15) 0.16261(14) 0.05526(12) 0.0603(5) Uani d . 1 C C1A 1.4751(2) 0.2423(2) -0.44474(19) 0.0768(7) Uani d . 1 C C2A 1.3835(2) 0.22130(17) -0.37188(16) 0.0633(6) Uani d . 1 C C3A 1.37741(18) 0.23070(17) -0.28404(15) 0.0592(5) Uani d . 1 C C4A 1.4644(2) 0.2586(2) -0.27045(19) 0.0694(6) Uani d . 1 C C5A 1.5568(2) 0.2793(2) -0.3441(2) 0.0797(7) Uani d . 1 C C6A 1.5616(2) 0.2712(2) -0.4298(2) 0.0828(8) Uani d . 1 C C7A 1.24083(19) 0.23127(17) -0.13209(16) 0.0601(5) Uani d . 1 C C8A 1.06366(18) 0.17239(16) -0.10458(15) 0.0560(5) Uani d . 1 C C9A 1.00097(19) 0.11965(16) -0.19892(15) 0.0570(5) Uani d . 1 C C10A 0.8514(2) 0.05770(19) -0.17312(16) 0.0669(6) Uani d . 1 C C11A 0.9056(2) 0.09250(17) -0.12981(15) 0.0588(5) Uani d . 1 C C12A 0.89075(18) 0.10777(16) -0.04093(15) 0.0566(5) Uani d . 1 C C13A 0.85326(19) 0.12591(17) 0.09490(15) 0.0588(5) Uani d . 1 C C14A 0.7926(2) 0.12113(19) 0.19094(15) 0.0646(6) Uani d . 1 C C15A 0.6993(3) 0.0874(2) 0.24127(19) 0.0844(8) Uani d . 1 C C16A 0.6803(3) 0.1005(3) 0.3317(2) 0.0943(9) Uani d . 1 C C17A 0.7622(3) 0.1399(3) 0.33005(19) 0.0890(9) Uani d . 1 C C18A 1.2889(4) 0.1795(3) -0.4606(2) 0.0944(9) Uani d . 1 C C19A 0.8914(3) 0.0366(2) -0.33535(19) 0.0781(7) Uani d . 1 C C20A 0.7725(3) 0.0201(2) -0.3120(2) 0.0757(7) Uani d . 1 C C21A 0.7471(3) -0.0041(3) -0.3900(3) 0.0960(10) Uani d . 1 C C22A 0.6300(4) -0.0260(4) -0.3629(4) 0.1158(14) Uani d . 1 O O1B 0.85787(15) 0.24873(14) -0.55214(11) 0.0771(5) Uani d . 1 O O2B 0.57986(15) 0.31651(15) -0.12631(12) 0.0829(5) Uani d . 1 O O3B 1.21344(15) 0.35088(18) -0.66246(13) 0.0947(6) Uani d . 1 N N1B 1.01712(16) 0.30987(15) -0.58938(13) 0.0605(5) Uani d . 1 N N2B 0.88489(16) 0.31312(15) -0.44787(13) 0.0599(5) Uani d . 1 N N3B 1.03549(15) 0.37727(14) -0.45036(12) 0.0574(4) Uani d . 1 N N4B 1.17808(15) 0.44127(14) -0.43220(13) 0.0601(5) Uani d . 1 N N5B 1.18979(15) 0.46648(14) -0.35848(13) 0.0591(5) Uani d . 1 N N6B 0.85096(15) 0.38809(14) -0.18119(12) 0.0604(5) Uani d . 1 N N7B 0.88282(14) 0.36002(13) -0.31875(11) 0.0528(4) Uani d . 1 N N8B 0.77962(14) 0.33578(14) -0.27164(12) 0.0571(4) Uani d . 1 C C1B 1.2444(3) 0.2883(3) -0.8021(2) 0.0897(9) Uani d . 1 C C2B 1.1810(2) 0.3098(2) -0.71638(16) 0.0704(6) Uani d . 1 C C3B 1.07312(18) 0.28892(17) -0.67781(14) 0.0585(5) Uani d . 1 C C4B 1.0305(2) 0.25047(19) -0.72733(16) 0.0656(6) Uani d . 1 C C5B 1.0945(3) 0.2300(2) -0.81245(18) 0.0801(7) Uani d . 1 C C6B 1.2014(3) 0.2480(3) -0.8489(2) 0.0918(9) Uani d . 1 C C7B 0.91880(18) 0.28774(17) -0.53427(14) 0.0573(5) Uani d . 1 C C8B 0.93964(17) 0.35111(15) -0.40910(14) 0.0525(5) Uani d . 1 C C9B 1.07977(17) 0.41167(16) -0.39875(15) 0.0545(5) Uani d . 1 C C10B 1.10419(19) 0.45399(17) -0.28249(17) 0.0604(6) Uani d . 1 C C11B 1.03001(18) 0.41875(16) -0.30628(15) 0.0556(5) Uani d . 1 C C12B 0.92377(18) 0.39100(16) -0.26342(14) 0.0541(5) Uani d . 1 C C13B 0.76576(18) 0.35480(17) -0.19028(15) 0.0567(5) Uani d . 1 C C14B 0.6663(2) 0.3447(2) -0.11459(16) 0.0663(6) Uani d . 1 C C15B 0.6222(14) 0.3839(12) -0.0354(14) 0.086(4) Uani d P 0.50 C C15C 0.6528(13) 0.3418(11) -0.0266(13) 0.076(3) Uani d P 0.50 C C16B 0.5166(17) 0.3651(11) 0.0087(13) 0.095(4) Uani d P 0.50 C C16C 0.5422(18) 0.3172(11) 0.0183(16) 0.103(5) Uani d P 0.50 C C17B 0.485(3) 0.331(3) -0.044(3) 0.091(6) Uani d P 0.50 C C17C 0.509(2) 0.304(3) -0.047(3) 0.093(7) Uani d P 0.50 C C18B 1.3233(3) 0.3724(4) -0.6945(3) 0.1020(11) Uani d . 1 C C19B 1.2914(2) 0.5024(2) -0.37002(18) 0.0659(6) Uani d . 1 C C20B 1.2907(2) 0.5286(2) -0.2837(2) 0.0694(6) Uani d . 1 C C21B 1.3957(3) 0.5645(3) -0.2930(2) 0.0898(9) Uani d . 1 C C22B 1.3902(4) 0.5925(4) -0.2052(3) 0.1091(12) Uani d . 1 O O50 1.3901(6) 0.0278(5) 0.0551(5) 0.106(2) Uani d P 0.50 O O50A 1.4158(7) -0.0344(7) 0.0750(5) 0.132(3) Uani d P 0.50 C C50 1.5102(4) -0.0104(4) -0.0876(3) 0.1274(14) Uani d . 1 C C51 1.4092(4) -0.0192(5) -0.0135(4) 0.161(2) Uani d . 1 O O60 1.0547(4) 0.4064(3) -0.0231(4) 0.1021(17) Uani d P 0.60 O O60A 1.0613(12) 0.4510(11) -0.0734(6) 0.163(5) Uani d P 0.40 C C60A 0.9371(7) 0.4840(10) -0.0501(7) 0.101(3) Uani d P 0.40 C C60 0.9325(6) 0.4312(5) 0.0293(8) 0.109(2) Uani d P 0.60 C C61 0.860(3) 0.515(3) 0.043(2) 0.203(17) Uani d P 0.30 C C61A 0.8868(5) 0.5329(6) 0.0057(8) 0.121(3) Uani d P 0.70 H H1 0.820(2) 0.2994(16) -0.4108(16) 0.059(6) Uiso d . 1 H H2 1.248(3) 0.230(2) -0.908(2) 0.099(9) Uiso d . 1 H H3 0.634(4) -0.107(3) -0.308(3) 0.163(16) Uiso d . 1 H H4 1.364(2) 0.4472(18) -0.3905(17) 0.073(7) Uiso d . 1 H H5 1.319(2) 0.406(2) -0.649(2) 0.082(9) Uiso d . 1 H H6 0.782(3) 0.162(2) 0.371(2) 0.104(10) Uiso d . 1 H H7 1.109(2) 0.2257(17) -0.0288(18) 0.067(7) Uiso d . 1 H H8 1.283(3) 0.244(2) -0.506(2) 0.114(12) Uiso d . 1 H H9 1.103(2) 0.4677(18) -0.2259(19) 0.077(7) Uiso d . 1 H H10 0.952(3) -0.029(2) -0.351(2) 0.095(9) Uiso d . 1 H H11 1.222(2) 0.583(2) -0.2691(18) 0.080(8) Uiso d . 1 H H12 1.313(3) 0.298(2) -0.816(2) 0.093(9) Uiso d . 1 H H13 0.957(2) 0.2395(18) -0.7034(19) 0.080(8) Uiso d . 1 H H14 1.478(2) 0.2307(19) -0.505(2) 0.086(8) Uiso d . 1 H H15 0.903(3) 0.093(2) -0.391(2) 0.111(10) Uiso d . 1 H H16 0.782(2) 0.0322(18) -0.1499(17) 0.074(7) Uiso d . 1 H H18 1.403(3) 0.617(3) -0.347(2) 0.113(11) Uiso d . 1 H H19 1.363(3) 0.125(2) -0.487(2) 0.112(10) Uiso d . 1 H H20 1.047(2) 0.3401(17) -0.5662(16) 0.064(7) Uiso d . 1 H H21 1.288(2) 0.469(2) -0.2359(18) 0.075(7) Uiso d . 1 H H22 0.483(4) 0.352(3) 0.070(3) 0.154(15) Uiso d . 1 H H23 1.619(3) 0.304(2) -0.330(2) 0.104(9) Uiso d . 1 H H25 1.220(3) 0.153(2) -0.448(2) 0.100(10) Uiso d . 1 H H26 1.627(3) 0.288(2) -0.481(2) 0.107(9) Uiso d . 1 H H27 0.818(3) -0.066(3) -0.415(2) 0.124(11) Uiso d . 1 H H28 0.619(3) 0.081(2) 0.387(2) 0.123(11) Uiso d . 1 H H29 0.656(3) 0.063(2) 0.217(2) 0.105(10) Uiso d . 1 H H30 1.2883(19) 0.5632(18) -0.4229(17) 0.069(7) Uiso d . 1 H H31 0.716(2) 0.079(2) -0.2944(19) 0.086(8) Uiso d . 1 H H32 0.678(3) 0.382(3) -0.008(3) 0.134(14) Uiso d . 1 H H34 0.763(2) -0.043(2) -0.255(2) 0.091(8) Uiso d . 1 H H35 1.231(2) 0.1896(18) -0.2318(17) 0.068(7) Uiso d . 1 H H36 1.303(4) 0.646(3) -0.178(3) 0.169(16) Uiso d . 1 H H37 1.064(3) 0.198(2) -0.844(2) 0.102(10) Uiso d . 1 H H38 0.435(3) 0.297(3) -0.049(2) 0.120(13) Uiso d . 1 H H39 0.610(4) -0.042(3) -0.409(3) 0.148(14) Uiso d . 1 H H40 1.388(3) 0.295(3) -0.702(2) 0.119(11) Uiso d . 1 H H41 1.448(4) 0.626(3) -0.215(3) 0.156(15) Uiso d . 1 H H42 1.472(4) 0.505(3) -0.319(3) 0.150(14) Uiso d . 1 H H43 1.328(3) 0.419(2) -0.750(2) 0.108(11) Uiso d . 1 H H44 0.573(3) 0.023(3) -0.336(3) 0.122(13) Uiso d . 1 H H45 1.400(3) 0.529(3) -0.158(3) 0.143(16) Uiso d . 1 H H48 0.757(3) 0.046(3) -0.439(3) 0.132(15) Uiso d . 1 H H51 1.463(2) 0.2659(19) -0.210(2) 0.087(8) Uiso d . 1 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 0.0636(10) 0.1176(14) 0.0770(11) -0.0392(9) -0.0016(8) -0.0463(10) O2A 0.0799(11) 0.1139(13) 0.0529(9) -0.0472(10) -0.0024(8) -0.0249(9) O3A 0.0827(12) 0.0999(12) 0.0569(10) -0.0395(9) -0.0071(8) -0.0242(8) N1A 0.0574(11) 0.0837(13) 0.0536(11) -0.0328(10) -0.0011(9) -0.0190(9) N2A 0.0599(11) 0.0922(14) 0.0525(11) -0.0349(10) 0.0034(9) -0.0301(10) N3A 0.0613(11) 0.0681(11) 0.0519(11) -0.0277(9) -0.0025(8) -0.0173(8) N4A 0.0751(13) 0.0694(11) 0.0547(11) -0.0302(9) -0.0060(9) -0.0175(9) N5A 0.0810(13) 0.0721(12) 0.0532(11) -0.0327(10) -0.0117(9) -0.0166(9) N6A 0.0645(11) 0.0817(12) 0.0508(10) -0.0348(9) -0.0030(9) -0.0169(9) N7A 0.0559(10) 0.0696(11) 0.0471(10) -0.0260(8) -0.0038(8) -0.0169(8) N8A 0.0591(11) 0.0771(12) 0.0475(10) -0.0270(9) -0.0017(8) -0.0194(8) C1A 0.0737(17) 0.0878(17) 0.0579(15) -0.0252(13) 0.0028(12) -0.0157(13) C2A 0.0580(13) 0.0683(13) 0.0585(14) -0.0197(10) -0.0040(10) -0.0139(10) C3A 0.0508(12) 0.0671(13) 0.0541(13) -0.0187(10) -0.0020(9) -0.0128(10) C4A 0.0560(14) 0.0880(17) 0.0649(16) -0.0261(12) -0.0074(11) -0.0171(13) C5A 0.0549(14) 0.0969(19) 0.0811(19) -0.0279(13) -0.0017(13) -0.0171(14) C6A 0.0579(15) 0.0975(19) 0.0767(19) -0.0273(13) 0.0074(13) -0.0129(14) C7A 0.0529(12) 0.0699(13) 0.0582(13) -0.0206(10) -0.0028(10) -0.0212(11) C8A 0.0537(12) 0.0618(12) 0.0520(12) -0.0219(9) -0.0013(9) -0.0166(9) C9A 0.0621(13) 0.0583(12) 0.0516(12) -0.0209(10) -0.0066(10) -0.0151(9) C10A 0.0769(16) 0.0784(15) 0.0536(13) -0.0360(13) -0.0088(12) -0.0160(11) C11A 0.0643(13) 0.0661(13) 0.0506(12) -0.0286(10) -0.0064(10) -0.0143(10) C12A 0.0565(12) 0.0634(12) 0.0533(12) -0.0260(10) -0.0064(10) -0.0133(9) C13A 0.0587(13) 0.0697(13) 0.0510(12) -0.0255(10) -0.0068(10) -0.0146(10) C14A 0.0633(14) 0.0845(15) 0.0515(13) -0.0325(12) -0.0033(10) -0.0193(11) C15A 0.0842(19) 0.115(2) 0.0645(16) -0.0549(17) 0.0062(14) -0.0291(15) C16A 0.101(2) 0.125(2) 0.0589(16) -0.0586(19) 0.0124(15) -0.0254(15) C17A 0.099(2) 0.125(2) 0.0508(15) -0.0506(19) 0.0020(14) -0.0289(15) C18A 0.100(2) 0.123(3) 0.074(2) -0.030(2) -0.0173(18) -0.043(2) C19A 0.109(2) 0.0799(18) 0.0597(15) -0.0383(16) -0.0186(15) -0.0219(14) C20A 0.0894(19) 0.0740(16) 0.0759(18) -0.0179(14) -0.0328(15) -0.0237(14) C21A 0.120(3) 0.098(2) 0.089(2) -0.018(2) -0.044(2) -0.039(2) C22A 0.119(3) 0.126(3) 0.143(4) -0.017(2) -0.066(3) -0.067(3) O1B 0.0685(10) 0.1187(13) 0.0632(10) -0.0503(10) -0.0013(8) -0.0339(9) O2B 0.0667(11) 0.1342(15) 0.0636(11) -0.0537(10) 0.0023(9) -0.0327(10) O3B 0.0652(11) 0.1592(18) 0.0675(11) -0.0609(12) -0.0012(9) -0.0159(11) N1B 0.0531(11) 0.0847(13) 0.0494(10) -0.0301(9) -0.0034(8) -0.0187(9) N2B 0.0503(10) 0.0886(13) 0.0491(10) -0.0339(9) -0.0010(8) -0.0211(9) N3B 0.0500(10) 0.0751(11) 0.0513(10) -0.0266(8) -0.0052(8) -0.0157(8) N4B 0.0504(10) 0.0743(11) 0.0596(11) -0.0260(8) -0.0092(8) -0.0139(9) N5B 0.0498(10) 0.0704(11) 0.0631(11) -0.0255(8) -0.0116(8) -0.0140(9) N6B 0.0554(10) 0.0809(12) 0.0511(10) -0.0296(9) -0.0057(8) -0.0178(9) N7B 0.0457(9) 0.0695(10) 0.0475(9) -0.0254(8) -0.0036(7) -0.0157(8) N8B 0.0485(10) 0.0757(11) 0.0506(10) -0.0280(8) -0.0016(8) -0.0167(8) C1B 0.0616(17) 0.125(2) 0.0634(17) -0.0294(16) 0.0067(13) -0.0112(16) C2B 0.0589(14) 0.0985(17) 0.0509(13) -0.0278(12) -0.0094(11) -0.0076(12) C3B 0.0525(12) 0.0708(13) 0.0442(11) -0.0167(10) -0.0041(9) -0.0087(10) C4B 0.0663(15) 0.0773(15) 0.0510(13) -0.0208(12) -0.0075(11) -0.0160(11) C5B 0.095(2) 0.0883(18) 0.0524(14) -0.0255(15) -0.0071(14) -0.0187(13) C6B 0.094(2) 0.114(2) 0.0533(16) -0.0215(17) 0.0019(15) -0.0248(15) C7B 0.0505(12) 0.0763(13) 0.0483(12) -0.0254(10) -0.0048(9) -0.0160(10) C8B 0.0478(11) 0.0645(12) 0.0466(11) -0.0192(9) -0.0064(9) -0.0146(9) C9B 0.0462(11) 0.0614(12) 0.0557(12) -0.0198(9) -0.0067(9) -0.0119(9) C10B 0.0544(13) 0.0740(14) 0.0590(14) -0.0263(10) -0.0107(11) -0.0158(11) C11B 0.0503(12) 0.0668(12) 0.0542(12) -0.0236(9) -0.0086(9) -0.0145(10) C12B 0.0502(11) 0.0656(12) 0.0500(12) -0.0222(9) -0.0089(9) -0.0134(9) C13B 0.0517(12) 0.0735(13) 0.0497(12) -0.0266(10) -0.0061(9) -0.0151(10) C14B 0.0575(13) 0.0978(17) 0.0533(13) -0.0379(12) -0.0023(10) -0.0224(12) C15B 0.066(8) 0.143(12) 0.065(5) -0.045(7) 0.003(5) -0.046(8) C15C 0.055(6) 0.126(10) 0.060(5) -0.039(5) 0.004(4) -0.039(7) C16B 0.088(9) 0.154(12) 0.058(5) -0.066(9) 0.022(5) -0.048(8) C16C 0.078(8) 0.159(13) 0.080(7) -0.062(9) 0.025(6) -0.052(10) C17B 0.059(10) 0.148(15) 0.070(7) -0.046(9) 0.017(7) -0.040(9) C17C 0.059(11) 0.17(2) 0.075(6) -0.066(13) 0.020(8) -0.056(11) C18B 0.072(2) 0.135(3) 0.098(3) -0.057(2) -0.0121(18) -0.001(3) C19B 0.0538(14) 0.0766(15) 0.0748(16) -0.0319(12) -0.0153(12) -0.0108(13) C20B 0.0572(15) 0.0782(17) 0.0818(18) -0.0298(13) -0.0145(13) -0.0189(14) C21B 0.079(2) 0.127(3) 0.087(2) -0.0608(19) -0.0094(16) -0.032(2) C22B 0.094(3) 0.162(4) 0.108(3) -0.073(3) -0.016(2) -0.044(3) O50 0.075(3) 0.136(5) 0.094(5) -0.029(3) 0.003(3) -0.029(4) O50A 0.127(6) 0.192(7) 0.096(4) -0.113(6) -0.026(4) 0.020(5) C50 0.104(3) 0.202(4) 0.098(3) -0.070(3) -0.011(2) -0.045(3) C51 0.129(4) 0.274(6) 0.129(4) -0.115(4) -0.010(3) -0.066(4) O60 0.072(3) 0.090(3) 0.169(5) -0.0003(19) -0.030(3) -0.087(3) O60A 0.147(8) 0.276(15) 0.107(7) -0.071(9) -0.008(6) -0.112(8) C60A 0.061(5) 0.170(9) 0.105(7) -0.022(5) -0.021(5) -0.086(7) C60 0.085(4) 0.095(4) 0.161(7) -0.028(3) -0.038(4) -0.033(4) C61 0.23(3) 0.32(4) 0.148(16) -0.21(3) 0.075(17) -0.16(2) C61A 0.051(3) 0.127(5) 0.212(10) -0.011(3) -0.014(4) -0.108(6) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C14A O2A C17A . . 105.9(2) C2A O3A C18A . . 119.4(2) C7A N1A C3A . . 126.6(2) C7A N1A H35 . . 115.0(17) C3A N1A H35 . . 117.6(17) C8A N2A C7A . . 129.4(2) C8A N2A H7 . . 115.0(16) C7A N2A H7 . . 115.2(16) C8A N3A C9A . . 116.88(18) C9A N4A N5A . . 103.09(17) C10A N5A N4A . . 113.87(19) C10A N5A C19A . . 127.9(2) N4A N5A C19A . . 118.2(2) C12A N6A C13A . . 102.87(17) C12A N7A N8A . . 110.43(16) C12A N7A C8A . . 123.98(18) N8A N7A C8A . . 125.52(17) C13A N8A N7A . . 100.98(17) C2A C1A C6A . . 119.6(3) C2A C1A H14 . . 116.8(16) C6A C1A H14 . . 123.5(16) O3A C2A C1A . . 126.1(2) O3A C2A C3A . . 113.88(19) C1A C2A C3A . . 120.1(2) C4A C3A C2A . . 119.5(2) C4A C3A N1A . . 125.7(2) C2A C3A N1A . . 114.9(2) C3A C4A C5A . . 120.2(3) C3A C4A H51 . . 121.6(16) C5A C4A H51 . . 118.2(16) C6A C5A C4A . . 120.0(3) C6A C5A H23 . . 123.1(17) C4A C5A H23 . . 116.8(17) C5A C6A C1A . . 120.6(2) C5A C6A H26 . . 118.4(18) C1A C6A H26 . . 120.9(18) O1A C7A N1A . . 126.8(2) O1A C7A N2A . . 118.5(2) N1A C7A N2A . . 114.8(2) N3A C8A N2A . . 124.04(19) N3A C8A N7A . . 121.70(19) N2A C8A N7A . . 114.26(19) N4A C9A N3A . . 123.30(19) N4A C9A C11A . . 111.71(19) N3A C9A C11A . . 125.0(2) N5A C10A C11A . . 106.4(2) N5A C10A H16 . . 122.6(15) C11A C10A H16 . . 131.0(15) C10A C11A C9A . . 105.0(2) C10A C11A C12A . . 138.3(2) C9A C11A C12A . . 116.76(19) N6A C12A N7A . . 109.37(19) N6A C12A C11A . . 135.0(2) N7A C12A C11A . . 115.59(18) N8A C13A N6A . . 116.35(19) N8A C13A C14A . . 123.6(2) N6A C13A C14A . . 120.02(19) C15A C14A O2A . . 110.3(2) C15A C14A C13A . . 131.4(2) O2A C14A C13A . . 118.26(19) C14A C15A C16A . . 106.2(3) C14A C15A H29 . . 124(2) C16A C15A H29 . . 129.5(19) C17A C16A C15A . . 106.8(3) C17A C16A H28 . . 126.4(19) C15A C16A H28 . . 126.7(19) C16A C17A O2A . . 110.8(3) C16A C17A H6 . . 137(2) O2A C17A H6 . . 112(2) O3A C18A H8 . . 113(2) O3A C18A H19 . . 110.1(18) H8 C18A H19 . . 108(3) O3A C18A H25 . . 106.3(18) H8 C18A H25 . . 110(3) H19 C18A H25 . . 108(2) N5A C19A C20A . . 112.5(2) N5A C19A H10 . . 110.6(16) C20A C19A H10 . . 108.9(16) N5A C19A H15 . . 106.0(18) C20A C19A H15 . . 111.6(18) H10 C19A H15 . . 107(2) C19A C20A C21A . . 113.4(3) C19A C20A H31 . . 109.5(16) C21A C20A H31 . . 109.6(17) C19A C20A H34 . . 110.5(15) C21A C20A H34 . . 106.4(15) H31 C20A H34 . . 107(2) C20A C21A C22A . . 112.2(3) C20A C21A H27 . . 108.7(18) C22A C21A H27 . . 113.5(18) C20A C21A H48 . . 109(2) C22A C21A H48 . . 114(3) H27 C21A H48 . . 99(3) C21A C22A H3 . . 108(2) C21A C22A H39 . . 116(3) H3 C22A H39 . . 99(3) C21A C22A H44 . . 112(2) H3 C22A H44 . . 108(3) H39 C22A H44 . . 112(3) C17C O2B C14B . . 106.4(16) C17C O2B C17B . . 15(3) C14B O2B C17B . . 105.5(17) C2B O3B C18B . . 118.4(3) C7B N1B C3B . . 127.0(2) C7B N1B H20 . . 113.9(16) C3B N1B H20 . . 119.1(16) C8B N2B C7B . . 129.99(18) C8B N2B H1 . . 113.4(15) C7B N2B H1 . . 116.5(15) C8B N3B C9B . . 116.14(18) C9B N4B N5B . . 103.05(17) C10B N5B N4B . . 113.87(17) C10B N5B C19B . . 127.8(2) N4B N5B C19B . . 118.37(18) C12B N6B C13B . . 102.85(17) C12B N7B N8B . . 110.53(16) C12B N7B C8B . . 124.68(17) N8B N7B C8B . . 124.76(17) C13B N8B N7B . . 100.76(16) C6B C1B C2B . . 120.6(3) C6B C1B H12 . . 128(2) C2B C1B H12 . . 111(2) O3B C2B C1B . . 126.6(2) O3B C2B C3B . . 113.9(2) C1B C2B C3B . . 119.5(3) C4B C3B C2B . . 118.8(2) C4B C3B N1B . . 125.8(2) C2B C3B N1B . . 115.4(2) C3B C4B C5B . . 120.9(3) C3B C4B H13 . . 119.3(17) C5B C4B H13 . . 119.7(17) C6B C5B C4B . . 120.1(3) C6B C5B H37 . . 121.0(19) C4B C5B H37 . . 118.8(19) C1B C6B C5B . . 120.1(3) C1B C6B H2 . . 120.6(17) C5B C6B H2 . . 119.2(17) O1B C7B N1B . . 126.6(2) O1B C7B N2B . . 118.19(18) N1B C7B N2B . . 115.18(19) N3B C8B N2B . . 124.54(19) N3B C8B N7B . . 121.84(19) N2B C8B N7B . . 113.61(17) N4B C9B N3B . . 122.82(19) N4B C9B C11B . . 111.92(19) N3B C9B C11B . . 125.26(18) N5B C10B C11B . . 105.8(2) N5B C10B H9 . . 121.9(15) C11B C10B H9 . . 132.3(15) C10B C11B C9B . . 105.39(19) C10B C11B C12B . . 137.4(2) C9B C11B C12B . . 117.17(19) N6B C12B N7B . . 109.42(17) N6B C12B C11B . . 135.8(2) N7B C12B C11B . . 114.81(18) N8B C13B N6B . . 116.44(18) N8B C13B C14B . . 123.57(19) N6B C13B C14B . . 120.0(2) C15C C14B O2B . . 111.0(8) C15C C14B C15B . . 25.2(9) O2B C14B C15B . . 106.8(8) C15C C14B C13B . . 128.7(8) O2B C14B C13B . . 119.2(2) C15B C14B C13B . . 131.6(9) C15C C15B C16B . . 100(4) C15C C15B C14B . . 72(3) C16B C15B C14B . . 109.3(16) C15C C15B C16C . . 75(4) C16B C15B C16C . . 25.4(11) C14B C15B C16C . . 98.9(14) C15C C15B H32 . . 67(4) C16B C15B H32 . . 127(3) C14B C15B H32 . . 114(3) C16C C15B H32 . . 116(3) C15B C15C C14B . . 83(4) C15B C15C C16C . . 82(4) C14B C15C C16C . . 103.8(16) C15B C15C C16B . . 58(3) C14B C15C C16B . . 100.7(13) C16C C15C C16B . . 23.9(9) C15B C15C H32 . . 74(4) C14B C15C H32 . . 123(3) C16C C15C H32 . . 123(3) C16B C15C H32 . . 109(3) C16C C16B C17B . . 80(4) C16C C16B C15B . . 89(4) C17B C16B C15B . . 109(2) C16C C16B C17C . . 65(4) C17B C16B C17C . . 16(3) C15B C16B C17C . . 101.6(19) C16C C16B C15C . . 67(3) C17B C16B C15C . . 105.2(17) C15B C16B C15C . . 21.8(11) C17C C16B C15C . . 93.2(16) C16C C16B H22 . . 81(4) C17B C16B H22 . . 118(4) C15B C16B H22 . . 129(3) C17C C16B H22 . . 118(3) C15C C16B H22 . . 120(3) C16B C16C C17C . . 89(5) C16B C16C C17B . . 72(4) C17C C16C C17B . . 18(3) C16B C16C C15C . . 89(4) C17C C16C C15C . . 105(2) C17B C16C C15C . . 110(2) C16B C16C C15B . . 66(3) C17C C16C C15B . . 102(2) C17B C16C C15B . . 100(2) C15C C16C C15B . . 23.2(8) C16B C16C H22 . . 61(4) C17C C16C H22 . . 121(3) C17B C16C H22 . . 106(3) C15C C16C H22 . . 122(3) C15B C16C H22 . . 108(3) C16B C17B C16C . . 28.3(14) C16B C17B O2B . . 108(3) C16C C17B O2B . . 101(2) C16B C17B H38 . . 147(5) C16C C17B H38 . . 134(5) O2B C17B H38 . . 102(4) O2B C17C C16C . . 113(2) O2B C17C C16B . . 110(2) C16C C17C C16B . . 26.3(12) O2B C17C H38 . . 114(4) C16C C17C H38 . . 132(4) C16B C17C H38 . . 123(3) O3B C18B H5 . . 100.4(18) O3B C18B H40 . . 104.8(17) H5 C18B H40 . . 121(2) O3B C18B H43 . . 111(2) H5 C18B H43 . . 108(3) H40 C18B H43 . . 111(3) N5B C19B C20B . . 111.9(2) N5B C19B H4 . . 108.3(13) C20B C19B H4 . . 111.7(14) N5B C19B H30 . . 105.1(13) C20B C19B H30 . . 112.6(13) H4 C19B H30 . . 106.8(19) C19B C20B C21B . . 113.2(2) C19B C20B H11 . . 108.1(16) C21B C20B H11 . . 108.5(15) C19B C20B H21 . . 108.0(15) C21B C20B H21 . . 109.3(15) H11 C20B H21 . . 110(2) C22B C21B C20B . . 111.5(3) C22B C21B H18 . . 116(2) C20B C21B H18 . . 108(2) C22B C21B H42 . . 117(2) C20B C21B H42 . . 106(2) H18 C21B H42 . . 97(3) C21B C22B H36 . . 112(2) C21B C22B H41 . . 111(3) H36 C22B H41 . . 107(3) C21B C22B H45 . . 108(2) H36 C22B H45 . . 107(3) H41 C22B H45 . . 111(3) O50A O50 C51 . . 73.9(10) O50A O50 C50 . 2_855 69.4(9) C51 O50 C50 . 2_855 114.5(5) O50 O50A C51 . . 70.6(9) O50 O50A C50 . 2_855 76.3(10) C51 O50A C50 . 2_855 116.3(5) O50A C50 O50 2_855 2_855 34.3(3) O50A C50 C51 2_855 . 116.0(5) O50 C50 C51 2_855 . 112.0(4) O50 C51 O50A . . 35.6(4) O50 C51 C50 . . 116.8(5) O50A C51 C50 . . 119.4(5) O60A O60 C61A . 2_765 78.9(11) O60A O60 C60 . . 107.9(12) C61A O60 C60 2_765 . 108.6(6) O60A O60 C60A . . 61.9(11) C61A O60 C60A 2_765 . 107.1(5) C60 O60 C60A . . 47.0(4) O60A O60 C61 . 2_765 61.3(18) C61A O60 C61 2_765 2_765 20.0(11) C60 O60 C61 . 2_765 121.3(10) C60A O60 C61 . 2_765 103.6(17) O60 O60A C60A . . 86.5(13) O60 O60A C61 . 2_765 88.4(19) C60A O60A C61 . 2_765 126.3(14) O60 O60A C61A . 2_765 67.6(10) C60A O60A C61A . 2_765 112.7(7) C61 O60A C61A 2_765 2_765 23.0(12) O60 O60A C60 . . 47.1(9) C60A O60A C60 . . 40.4(5) C61 O60A C60 2_765 . 107.8(11) C61A O60A C60 2_765 . 86.0(6) C61A C60A C60 . . 67.6(7) C61A C60A O60A . . 121.0(8) C60 C60A O60A . . 91.1(9) C61A C60A C61 . . 19.0(15) C60 C60A C61 . . 51.7(17) O60A C60A C61 . . 124.8(15) C61A C60A O60 . . 109.2(8) C60 C60A O60 . . 60.3(7) O60A C60A O60 . . 31.6(5) C61 C60A O60 . . 103.4(18) C60A C60 C61 . . 77.4(17) C60A C60 C61A . . 53.4(6) C61 C60 C61A . . 26.4(14) C60A C60 O60 . . 72.7(7) C61 C60 O60 . . 132.2(14) C61A C60 O60 . . 108.5(7) C60A C60 O60A . . 48.4(6) C61 C60 O60A . . 112.0(15) C61A C60 O60A . . 86.2(7) O60 C60 O60A . . 25.0(5) C61A C61 C60 . . 85(4) C61A C61 O60A . 2_765 82(3) C60 C61 O60A . 2_765 94(3) C61A C61 C60A . . 39(3) C60 C61 C60A . . 50.9(10) O60A C61 C60A 2_765 . 102.9(16) C61A C61 O60 . 2_765 55(3) C60 C61 O60 . 2_765 102.9(19) O60A C61 O60 2_765 2_765 30.3(6) C60A C61 O60 . 2_765 86.2(12) C61 C61A C60A . . 122(4) C61 C61A C60 . . 69(4) C60A C61A C60 . . 59.0(7) C61 C61A O60 . 2_765 105(3) C60A C61A O60 . 2_765 117.8(8) C60 C61A O60 . 2_765 113.7(6) C61 C61A O60A . 2_765 75(3) C60A C61A O60A . 2_765 125.1(7) C60 C61A O60A . 2_765 89.2(8) O60 C61A O60A 2_765 2_765 33.5(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1A C7A . 1.214(3) O2A C14A . 1.359(3) O2A C17A . 1.365(3) O3A C2A . 1.366(3) O3A C18A . 1.406(3) N1A C7A . 1.336(3) N1A C3A . 1.412(3) N1A H35 . 0.87(3) N2A C8A . 1.364(3) N2A C7A . 1.406(3) N2A H7 . 0.84(3) N3A C8A . 1.291(3) N3A C9A . 1.374(3) N4A C9A . 1.337(3) N4A N5A . 1.366(3) N5A C10A . 1.336(3) N5A C19A . 1.468(3) N6A C12A . 1.325(3) N6A C13A . 1.366(3) N7A C12A . 1.371(3) N7A N8A . 1.373(2) N7A C8A . 1.398(3) N8A C13A . 1.329(3) C1A C2A . 1.383(3) C1A C6A . 1.388(4) C1A H14 . 1.00(3) C2A C3A . 1.399(3) C3A C4A . 1.375(3) C4A C5A . 1.395(3) C4A H51 . 0.98(3) C5A C6A . 1.363(4) C5A H23 . 1.06(3) C6A H26 . 0.99(3) C9A C11A . 1.413(3) C10A C11A . 1.373(3) C10A H16 . 0.98(3) C11A C12A . 1.418(3) C13A C14A . 1.448(3) C14A C15A . 1.339(3) C15A C16A . 1.419(4) C15A H29 . 0.95(3) C16A C17A . 1.316(4) C16A H28 . 1.00(4) C17A H6 . 0.93(3) C18A H8 . 0.97(3) C18A H19 . 1.06(4) C18A H25 . 0.99(3) C19A C20A . 1.506(4) C19A H10 . 1.02(3) C19A H15 . 1.00(3) C20A C21A . 1.512(4) C20A H31 . 0.94(3) C20A H34 . 1.07(3) C21A C22A . 1.512(6) C21A H27 . 1.08(4) C21A H48 . 0.89(4) C22A H3 . 1.21(4) C22A H39 . 0.93(4) C22A H44 . 0.90(4) O1B C7B . 1.217(3) O2B C17C . 1.29(4) O2B C14B . 1.357(3) O2B C17B . 1.47(3) O3B C2B . 1.374(3) O3B C18B . 1.418(3) N1B C7B . 1.340(3) N1B C3B . 1.410(3) N1B H20 . 0.86(2) N2B C8B . 1.357(3) N2B C7B . 1.401(3) N2B H1 . 0.88(2) N3B C8B . 1.293(2) N3B C9B . 1.380(3) N4B C9B . 1.337(3) N4B N5B . 1.369(3) N5B C10B . 1.341(3) N5B C19B . 1.471(3) N6B C12B . 1.322(3) N6B C13B . 1.367(3) N7B C12B . 1.368(3) N7B N8B . 1.375(2) N7B C8B . 1.391(3) N8B C13B . 1.327(3) C1B C6B . 1.365(5) C1B C2B . 1.390(4) C1B H12 . 0.87(3) C2B C3B . 1.392(3) C3B C4B . 1.377(3) C4B C5B . 1.379(3) C4B H13 . 0.93(3) C5B C6B . 1.364(4) C5B H37 . 0.98(3) C6B H2 . 0.98(3) C9B C11B . 1.404(3) C10B C11B . 1.380(3) C10B H9 . 0.96(3) C11B C12B . 1.421(3) C13B C14B . 1.439(3) C14B C15C . 1.325(19) C14B C15B . 1.384(18) C15B C15C . 0.59(2) C15B C16B . 1.36(3) C15B C16C . 1.49(3) C15B H32 . 0.92(4) C15C C16C . 1.45(3) C15C C16B . 1.58(2) C15C H32 . 0.88(4) C16B C16C . 0.64(2) C16B C17B . 1.29(5) C16B C17C . 1.44(4) C16B H22 . 0.91(5) C16C C17C . 1.31(5) C16C C17B . 1.33(5) C16C H22 . 1.03(5) C17B H38 . 0.94(5) C17C H38 . 0.97(6) C18B H5 . 0.95(3) C18B H40 . 1.14(3) C18B H43 . 0.92(3) C19B C20B . 1.502(4) C19B H4 . 1.02(2) C19B H30 . 1.00(2) C20B C21B . 1.520(3) C20B H11 . 0.96(3) C20B H21 . 0.95(3) C21B C22B . 1.516(5) C21B H18 . 0.95(3) C21B H42 . 1.10(4) C22B H36 . 1.14(5) C22B H41 . 0.95(5) C22B H45 . 0.97(4) O50 O50A . 0.828(8) O50 C51 . 1.342(9) O50 C50 2_855 1.428(8) O50A C51 . 1.367(9) O50A C50 2_855 1.376(8) C50 O50A 2_855 1.376(8) C50 O50 2_855 1.428(8) C50 C51 . 1.437(6) O60 O60A . 0.852(11) O60 C61A 2_765 1.427(10) O60 C60 . 1.476(9) O60 C60A . 1.623(12) O60 C61 2_765 1.69(3) O60A C60A . 1.435(15) O60A C61 2_765 1.48(3) O60A C61A 2_765 1.514(14) O60A C60 . 1.917(14) C60A C61A . 1.164(11) C60A C60 . 1.244(11) C60A C61 . 1.56(2) C60 C61 . 1.26(4) C60 C61A . 1.341(11) C61 C61A . 0.60(3) C61 O60A 2_765 1.48(3) C61 O60 2_765 1.69(3) C61A O60 2_765 1.427(9) C61A O60A 2_765 1.514(14)