Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_date 2006-12-26 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Shin-ichi Kondo' _publ_contact_author_address ; Department of Chemistry Gunma University 1-5-1 Tenjin-cho Kiryu Gunma 376-8515 JAPAN ; _publ_contact_author_email KONDO@CHEM.GUNMA-U.AC.JP _publ_section_title ; Synthesis of Cyclic Bis- and Trismelamine Derivatives and Their Complexation Properties with Barbiturates ; loop_ _publ_author_name S.Kondo T.Hayashi Y.Sakuno Y.Takezawa M.Unno Y.Yano T.Yokoyama #============================================================================== data___Host-guest _database_code_depnum_ccdc_archive 'CCDC 625414' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C69 H100 N22 O6 ' _chemical_formula_moiety 'C69 H100 N22 O6 ' _chemical_formula_weight 1333.69 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 14.995(2) _cell_length_b 15.949(2) _cell_length_c 17.6433(4) _cell_angle_alpha 68.348(10) _cell_angle_beta 71.330(10) _cell_angle_gamma 88.860(10) _cell_volume 3692.2(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 20400 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 32.6 _cell_measurement_temperature 113.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432.00 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.271 _exptl_absorpt_correction_T_max 0.992 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku RAXIS-IV++' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 39399 _diffrn_reflns_av_R_equivalents 0.1245 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.730 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.927 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 15745 _reflns_number_gt 5059 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.1391 _refine_ls_R_factor_gt 0.0836 _refine_ls_wR_factor_ref 0.2368 _refine_ls_wR_factor_gt 0.2003 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 15745 _refine_ls_number_parameters 885 _refine_ls_goodness_of_fit_ref 0.830 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.414 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.069 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N31 N -0.4465(2) 0.2067(2) 1.0764(2) 0.0442(8) Uani 1 1 d . . . N41 N 0.1375(2) 0.0325(2) 0.46849(18) 0.0367(8) Uani 1 1 d . . . H115 H 0.0988 0.0153 0.4472 0.044 Uiso 1 1 calc R . . N34 N -0.0678(2) 0.1214(2) 0.8327(2) 0.0425(8) Uani 1 1 d . . . N42 N 0.1548(2) 0.0611(2) 0.58571(18) 0.0355(7) Uani 1 1 d . . . H96 H 0.1284 0.0665 0.6357 0.043 Uiso 1 1 calc R . . N40 N 0.1163(2) 0.4342(2) 0.9092(2) 0.0418(8) Uani 1 1 d . . . N36 N 0.2179(2) 0.1202(2) 0.7458(2) 0.0412(8) Uani 1 1 d . . . H108 H 0.2408 0.1027 0.7022 0.049 Uiso 1 1 calc R . . N7 N -0.3800(2) 0.3311(2) 0.81698(19) 0.0424(8) Uani 1 1 d . . . H103 H -0.3482 0.3855 0.7923 0.051 Uiso 1 1 calc R . . O6 O -0.13775(19) 0.39622(19) 0.95481(16) 0.0447(7) Uani 1 1 d . . . N9 N -0.4604(2) 0.2096(2) 0.9437(2) 0.0428(8) Uani 1 1 d . . . C102 C 0.3111(3) 0.3139(3) 0.7462(2) 0.0383(9) Uani 1 1 d . . . H116 H 0.2608 0.3047 0.7986 0.046 Uiso 1 1 calc R . . C101 C 0.2845(3) 0.1462(3) 0.7805(2) 0.0428(10) Uani 1 1 d . . . H117 H 0.3311 0.1014 0.7860 0.051 Uiso 1 1 calc R . . H118 H 0.2495 0.1447 0.8391 0.051 Uiso 1 1 calc R . . N12 N 0.1616(2) 0.3893(2) 1.03595(19) 0.0405(8) Uani 1 1 d . . . C104 C -0.1149(3) 0.4273(3) 0.8764(2) 0.0388(9) Uani 1 1 d . . . C103 C 0.0979(3) 0.4030(3) 0.9961(2) 0.0380(9) Uani 1 1 d . . . C105 C 0.0985(3) 0.0393(3) 0.5477(2) 0.0340(8) Uani 1 1 d . . . N16 N 0.0729(2) 0.0938(2) 0.73672(18) 0.0363(7) Uani 1 1 d . . . O8 O 0.00967(18) 0.0250(2) 0.58313(16) 0.0429(7) Uani 1 1 d . . . N18 N -0.1799(2) 0.4324(2) 0.8347(2) 0.0440(8) Uani 1 1 d . . . H97 H -0.2387 0.4093 0.8674 0.053 Uiso 1 1 calc R . . O9 O 0.25966(19) 0.0502(2) 0.34695(16) 0.0492(8) Uani 1 1 d . . . N20 N -0.3567(2) 0.3250(2) 0.94080(19) 0.0410(8) Uani 1 1 d . . . C98 C -0.3990(3) 0.2861(3) 0.9037(2) 0.0393(9) Uani 1 1 d . . . N22 N 0.0859(2) 0.1472(2) 0.8425(2) 0.0407(8) Uani 1 1 d . . . O10 O 0.30011(18) 0.0900(2) 0.58865(16) 0.0449(7) Uani 1 1 d . . . N24 N -0.0215(2) 0.4590(2) 0.82414(19) 0.0415(8) Uani 1 1 d . . . H98 H 0.0209 0.4526 0.8501 0.050 Uiso 1 1 calc R . . O7 O 0.0943(2) 0.5297(2) 0.69552(18) 0.0568(8) Uani 1 1 d . . . C100 C 0.1242(3) 0.1215(3) 0.7764(2) 0.0341(8) Uani 1 1 d . . . C99 C -0.0237(3) 0.0934(3) 0.7691(2) 0.0394(9) Uani 1 1 d . . . C106 C 0.2509(3) 0.0748(3) 0.5494(2) 0.0382(9) Uani 1 1 d . . . N38 N 0.2799(2) 0.4294(2) 0.8959(2) 0.0412(8) Uani 1 1 d . . . O5 O -0.2243(2) 0.4733(2) 0.71698(17) 0.0553(8) Uani 1 1 d . . . N30 N 0.0051(2) 0.3842(2) 1.0458(2) 0.0441(8) Uani 1 1 d . . . H119 H -0.0371 0.3998 1.0196 0.053 Uiso 1 1 calc R . . C32 C 0.4209(3) 0.3955(3) 0.9646(3) 0.0499(11) Uani 1 1 d . . . H120 H 0.4222 0.3616 0.9273 0.060 Uiso 1 1 calc R . . H121 H 0.4562 0.3636 1.0038 0.060 Uiso 1 1 calc R . . C33 C -0.1608(3) 0.4704(3) 0.7467(2) 0.0414(10) Uani 1 1 d . . . C34 C -0.2894(3) 0.1848(3) 0.7526(3) 0.0441(10) Uani 1 1 d . . . H132 H -0.3170 0.1551 0.8137 0.053 Uiso 1 1 calc R . . C35 C -0.1164(3) 0.2736(3) 1.1707(2) 0.0390(9) Uani 1 1 d . . . C36 C -0.4811(3) 0.1741(3) 1.0298(2) 0.0407(9) Uani 1 1 d . . . C37 C -0.1773(3) 0.0633(3) 0.7553(3) 0.0493(11) Uani 1 1 d . . . H109 H -0.2039 0.0496 0.8182 0.059 Uiso 1 1 calc R . . H110 H -0.2021 0.0131 0.7447 0.059 Uiso 1 1 calc R . . C38 C -0.0096(3) 0.1463(3) 0.8676(2) 0.0419(10) Uani 1 1 d . . . C39 C 0.3572(3) 0.4012(3) 0.6939(2) 0.0420(10) Uani 1 1 d . . . C40 C 0.3314(3) 0.4820(3) 0.7180(3) 0.0474(10) Uani 1 1 d . . . H122 H 0.3756 0.4927 0.7456 0.057 Uiso 1 1 calc R . . H123 H 0.3405 0.5361 0.6643 0.057 Uiso 1 1 calc R . . C41 C 0.2324(3) 0.0504(3) 0.4200(2) 0.0374(9) Uani 1 1 d . . . N32 N -0.5440(2) 0.0981(2) 1.0752(2) 0.0451(9) Uani 1 1 d . . . C43 C -0.3847(3) 0.2824(3) 1.0279(3) 0.0418(10) Uani 1 1 d . . . C44 C -0.5730(3) 0.0556(3) 1.1691(2) 0.0478(11) Uani 1 1 d . . . H111 H -0.6386 0.0258 1.1922 0.057 Uiso 1 1 calc R . . H112 H -0.5725 0.1031 1.1927 0.057 Uiso 1 1 calc R . . C45 C 0.3370(3) 0.2404(3) 0.7236(3) 0.0458(10) Uani 1 1 d . . . N29 N -0.3490(2) 0.3218(3) 1.0693(2) 0.0499(10) Uani 1 1 d . . . H113 H -0.3132 0.3739 1.0376 0.060 Uiso 1 1 calc R . . N37 N 0.2342(2) 0.4728(2) 0.7765(2) 0.0445(8) Uani 1 1 d . . . H124 H 0.1889 0.4868 0.7538 0.053 Uiso 1 1 calc R . . C49 C -0.1996(3) 0.3054(3) 1.1594(2) 0.0397(9) Uani 1 1 d . . . H133 H -0.2021 0.3690 1.1356 0.048 Uiso 1 1 calc R . . C50 C 0.0105(3) 0.4996(3) 0.7354(2) 0.0437(10) Uani 1 1 d . . . C51 C -0.0601(3) 0.5083(3) 0.6874(2) 0.0415(10) Uani 1 1 d . . . C52 C -0.2807(3) 0.2465(3) 1.1821(2) 0.0425(10) Uani 1 1 d . . . C53 C 0.2102(3) 0.4440(3) 0.8637(2) 0.0392(9) Uani 1 1 d . . . C54 C -0.1141(3) 0.1805(3) 1.2074(3) 0.0493(11) Uani 1 1 d . . . H134 H -0.0576 0.1572 1.2154 0.059 Uiso 1 1 calc R . . N39 N 0.3218(2) 0.3935(3) 1.0173(2) 0.0444(9) Uani 1 1 d . . . C56 C 0.3000(3) 0.0702(3) 0.4610(2) 0.0375(9) Uani 1 1 d . . . C57 C -0.4091(3) 0.2953(3) 0.7617(2) 0.0445(10) Uani 1 1 d . . . H104 H -0.4338 0.3437 0.7220 0.053 Uiso 1 1 calc R . . H105 H -0.4605 0.2450 0.7982 0.053 Uiso 1 1 calc R . . C58 C -0.1553(3) 0.1749(3) 0.9649(3) 0.0512(11) Uani 1 1 d . . . H135 H -0.1772 0.1966 0.9143 0.061 Uiso 1 1 calc R . . H136 H -0.1700 0.2189 0.9936 0.061 Uiso 1 1 calc R . . C59 C -0.0254(4) 0.4571(3) 0.6275(3) 0.0549(12) Uani 1 1 d . . . H152 H -0.0676 0.4650 0.5927 0.066 Uiso 1 1 calc R . . H153 H 0.0387 0.4855 0.5868 0.066 Uiso 1 1 calc R . . C60 C -0.3267(3) 0.2615(3) 0.7095(3) 0.0457(11) Uani 1 1 d . . . N35 N -0.0515(2) 0.1722(2) 0.9345(2) 0.0445(9) Uani 1 1 d . . . N33 N -0.0746(2) 0.0659(2) 0.7305(2) 0.0454(9) Uani 1 1 d . . . H114 H -0.0443 0.0486 0.6880 0.055 Uiso 1 1 calc R . . C63 C 0.2521(3) 0.4041(3) 0.9825(3) 0.0423(10) Uani 1 1 d . . . C64 C 0.3617(3) 0.1614(3) 0.4003(2) 0.0482(11) Uani 1 1 d . . . H125 H 0.4096 0.1705 0.4251 0.058 Uiso 1 1 calc R . . H126 H 0.3960 0.1577 0.3437 0.058 Uiso 1 1 calc R . . C65 C 0.3122(4) -0.1031(3) 0.5271(3) 0.0541(12) Uani 1 1 d . . . H99 H 0.2689 -0.1048 0.5835 0.065 Uiso 1 1 calc R . . H100 H 0.2734 -0.1182 0.4968 0.065 Uiso 1 1 calc R . . C66 C 0.0064(3) 0.1956(3) 0.9790(3) 0.0532(12) Uani 1 1 d . . . H137 H -0.0296 0.2312 1.0119 0.064 Uiso 1 1 calc R . . H138 H 0.0646 0.2344 0.9351 0.064 Uiso 1 1 calc R . . C67 C -0.2762(4) 0.1546(3) 1.2191(3) 0.0533(12) Uani 1 1 d . . . H139 H -0.3303 0.1134 1.2356 0.064 Uiso 1 1 calc R . . C68 C -0.0580(3) 0.6094(3) 0.6331(2) 0.0434(10) Uani 1 1 d . . . H68 H -0.0995 0.6155 0.5980 0.052 Uiso 1 1 calc R . . H69 H 0.0073 0.6332 0.5926 0.052 Uiso 1 1 calc R . . C69 C -0.2116(3) 0.1499(3) 0.7079(3) 0.0437(10) Uani 1 1 d . . . C70 C -0.0292(3) 0.3401(3) 1.1395(2) 0.0478(11) Uani 1 1 d . . . H57 H -0.0448 0.3865 1.1652 0.057 Uiso 1 1 calc R . . H58 H 0.0212 0.3074 1.1590 0.057 Uiso 1 1 calc R . . C71 C -0.5097(4) -0.0133(3) 1.1991(3) 0.0643(14) Uani 1 1 d . . . H32 H -0.5049 -0.0572 1.1714 0.096 Uiso 1 1 calc R . . H33 H -0.5362 -0.0451 1.2621 0.096 Uiso 1 1 calc R . . H34 H -0.4466 0.0172 1.1834 0.096 Uiso 1 1 calc R . . C72 C 0.0451(4) 0.7900(3) 0.6134(3) 0.0646(14) Uani 1 1 d . . . H70 H 0.0583 0.7821 0.6664 0.097 Uiso 1 1 calc R . . H71 H 0.0645 0.8532 0.5724 0.097 Uiso 1 1 calc R . . H72 H 0.0806 0.7496 0.5873 0.097 Uiso 1 1 calc R . . C73 C -0.5935(3) 0.0645(3) 1.0297(3) 0.0559(12) Uani 1 1 d . . . H106 H -0.6169 -0.0005 1.0641 0.067 Uiso 1 1 calc R . . H107 H -0.5479 0.0697 0.9729 0.067 Uiso 1 1 calc R . . C74 C -0.1731(3) 0.1955(4) 0.6182(3) 0.0592(13) Uani 1 1 d . . . H140 H -0.1220 0.1730 0.5858 0.071 Uiso 1 1 calc R . . C75 C -0.3645(3) 0.2860(3) 1.1616(2) 0.0555(13) Uani 1 1 d . . . H141 H -0.4195 0.2387 1.1919 0.067 Uiso 1 1 calc R . . H142 H -0.3799 0.3354 1.1833 0.067 Uiso 1 1 calc R . . C76 C -0.0210(4) 0.3560(3) 0.6719(3) 0.0652(14) Uani 1 1 d . . . H73 H -0.0860 0.3240 0.6989 0.078 Uiso 1 1 calc R . . H74 H 0.0062 0.3461 0.7184 0.078 Uiso 1 1 calc R . . C77 C 0.4591(4) 0.3399(4) 0.5939(3) 0.0695(15) Uani 1 1 d . . . H59 H 0.5095 0.3489 0.5416 0.083 Uiso 1 1 calc R . . C78 C 0.3644(3) -0.0074(3) 0.4728(3) 0.0509(11) Uani 1 1 d . . . H101 H 0.4032 -0.0053 0.4148 0.061 Uiso 1 1 calc R . . H102 H 0.4084 0.0040 0.5004 0.061 Uiso 1 1 calc R . . C79 C 0.4713(3) 0.4896(3) 0.9080(3) 0.0599(13) Uani 1 1 d . . . H127 H 0.4455 0.5172 0.8610 0.090 Uiso 1 1 calc R . . H128 H 0.5391 0.4859 0.8836 0.090 Uiso 1 1 calc R . . H129 H 0.4619 0.5269 0.9428 0.090 Uiso 1 1 calc R . . C80 C -0.2853(3) 0.3053(4) 0.6212(3) 0.0565(13) Uani 1 1 d . . . H143 H -0.3092 0.3581 0.5908 0.068 Uiso 1 1 calc R . . C81 C -0.1948(4) 0.1213(3) 1.2326(3) 0.0608(13) Uani 1 1 d . . . H144 H -0.1935 0.0577 1.2591 0.073 Uiso 1 1 calc R . . C82 C 0.4314(3) 0.4129(3) 0.6180(3) 0.0534(12) Uani 1 1 d . . . H60 H 0.4638 0.4718 0.5819 0.064 Uiso 1 1 calc R . . C83 C 0.4124(3) 0.2540(3) 0.6472(3) 0.0616(13) Uani 1 1 d . . . H61 H 0.4317 0.2037 0.6317 0.074 Uiso 1 1 calc R . . C84 C 0.2852(4) 0.2611(3) 1.1563(3) 0.0625(14) Uani 1 1 d . . . H45 H 0.2350 0.2361 1.1436 0.094 Uiso 1 1 calc R . . H46 H 0.2671 0.2448 1.2189 0.094 Uiso 1 1 calc R . . H47 H 0.3443 0.2361 1.1359 0.094 Uiso 1 1 calc R . . C85 C -0.2080(3) 0.2720(4) 0.5763(3) 0.0655(15) Uani 1 1 d . . . H145 H -0.1791 0.3031 0.5156 0.079 Uiso 1 1 calc R . . C86 C 0.0401(5) 0.3157(4) 0.6070(3) 0.0795(19) Uani 1 1 d . . . H75 H 0.0273 0.2486 0.6336 0.095 Uiso 1 1 calc R . . H76 H 0.0217 0.3370 0.5544 0.095 Uiso 1 1 calc R . . C87 C 0.2995(3) 0.3638(3) 1.1104(3) 0.0503(11) Uani 1 1 d . . . H130 H 0.2412 0.3889 1.1345 0.060 Uiso 1 1 calc R . . H131 H 0.3517 0.3884 1.1219 0.060 Uiso 1 1 calc R . . C88 C -0.2085(3) 0.0836(3) 1.0273(3) 0.0595(13) Uani 1 1 d . . . H146 H -0.1982 0.0409 0.9979 0.089 Uiso 1 1 calc R . . H147 H -0.2763 0.0896 1.0481 0.089 Uiso 1 1 calc R . . H148 H -0.1855 0.0608 1.0766 0.089 Uiso 1 1 calc R . . C89 C 0.3656(5) 0.3339(4) 0.3237(4) 0.0889(19) Uani 1 1 d . . . H77 H 0.4087 0.3257 0.2718 0.107 Uiso 1 1 calc R . . H78 H 0.3227 0.3787 0.3046 0.107 Uiso 1 1 calc R . . C90 C 0.3064(4) 0.2439(3) 0.3854(3) 0.0656(14) Uani 1 1 d . . . H79 H 0.2572 0.2338 0.3623 0.079 Uiso 1 1 calc R . . H80 H 0.2736 0.2483 0.4419 0.079 Uiso 1 1 calc R . . C91 C 0.3331(4) -0.2659(4) 0.5947(3) 0.0772(16) Uani 1 1 d . . . H81 H 0.2865 -0.2675 0.6490 0.116 Uiso 1 1 calc R . . H82 H 0.3804 -0.3071 0.6076 0.116 Uiso 1 1 calc R . . H83 H 0.3010 -0.2851 0.5624 0.116 Uiso 1 1 calc R . . C92 C -0.6767(4) 0.1172(4) 1.0154(3) 0.0656(14) Uani 1 1 d . . . H35 H -0.7232 0.1104 1.0716 0.098 Uiso 1 1 calc R . . H36 H -0.7065 0.0935 0.9843 0.098 Uiso 1 1 calc R . . H37 H -0.6538 0.1816 0.9812 0.098 Uiso 1 1 calc R . . C93 C -0.0596(4) 0.7673(3) 0.6350(3) 0.0645(14) Uani 1 1 d . . . H84 H -0.0956 0.8030 0.6678 0.077 Uiso 1 1 calc R . . H85 H -0.0743 0.7845 0.5807 0.077 Uiso 1 1 calc R . . C94 C 0.0337(4) 0.1135(4) 1.0402(3) 0.0620(14) Uani 1 1 d . . . H149 H -0.0236 0.0758 1.0850 0.093 Uiso 1 1 calc R . . H150 H 0.0725 0.1330 1.0674 0.093 Uiso 1 1 calc R . . H151 H 0.0701 0.0783 1.0079 0.093 Uiso 1 1 calc R . . C95 C 0.3806(5) -0.1723(4) 0.5421(4) 0.0869(19) Uani 1 1 d . . . H86 H 0.4236 -0.1702 0.4854 0.104 Uiso 1 1 calc R . . H87 H 0.4196 -0.1564 0.5717 0.104 Uiso 1 1 calc R . . C96 C 0.4214(5) 0.3709(5) 0.3595(5) 0.132(3) Uani 1 1 d . . . H88 H 0.3835 0.3636 0.4187 0.198 Uiso 1 1 calc R . . H89 H 0.4411 0.4355 0.3238 0.198 Uiso 1 1 calc R . . H90 H 0.4777 0.3387 0.3603 0.198 Uiso 1 1 calc R . . C97 C 0.1455(5) 0.3428(5) 0.5814(4) 0.106(2) Uani 1 1 d . . . H91 H 0.1588 0.4091 0.5535 0.158 Uiso 1 1 calc R . . H92 H 0.1815 0.3156 0.5410 0.158 Uiso 1 1 calc R . . H93 H 0.1641 0.3213 0.6332 0.158 Uiso 1 1 calc R . . C10 C -0.0902(4) 0.6680(3) 0.6878(3) 0.0573(12) Uani 1 1 d . . . H94 H -0.1601 0.6583 0.7140 0.069 Uiso 1 1 calc R . . H95 H -0.0635 0.6481 0.7354 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N31 0.0345(19) 0.052(2) 0.0443(19) -0.0183(16) -0.0111(15) -0.0017(17) N41 0.0345(18) 0.045(2) 0.0360(17) -0.0217(14) -0.0114(14) -0.0011(15) N34 0.0373(19) 0.053(2) 0.0445(19) -0.0307(17) -0.0092(15) 0.0012(17) N42 0.0336(18) 0.039(2) 0.0319(16) -0.0153(13) -0.0058(13) -0.0044(14) N40 0.0326(19) 0.044(2) 0.052(2) -0.0223(16) -0.0137(15) 0.0031(16) N36 0.0356(19) 0.051(2) 0.0506(19) -0.0325(17) -0.0161(15) 0.0054(16) N7 0.041(2) 0.049(2) 0.0341(17) -0.0164(15) -0.0077(14) -0.0042(16) O6 0.0435(17) 0.053(2) 0.0337(15) -0.0115(12) -0.0132(12) -0.0048(14) N9 0.0333(19) 0.049(2) 0.0441(19) -0.0215(16) -0.0063(14) -0.0039(16) C102 0.030(2) 0.046(3) 0.039(2) -0.0198(18) -0.0077(16) -0.0011(18) C101 0.043(2) 0.048(3) 0.044(2) -0.0220(19) -0.0175(18) -0.001(2) N12 0.0340(19) 0.047(2) 0.0377(17) -0.0169(15) -0.0078(14) 0.0002(16) C104 0.035(2) 0.042(3) 0.036(2) -0.0138(17) -0.0092(16) -0.0022(18) C103 0.038(2) 0.041(3) 0.040(2) -0.0204(17) -0.0137(17) 0.0027(18) C105 0.033(2) 0.035(2) 0.0293(18) -0.0128(15) -0.0041(15) -0.0024(17) N16 0.0327(18) 0.041(2) 0.0360(16) -0.0166(14) -0.0101(13) -0.0039(15) O8 0.0334(16) 0.056(2) 0.0441(15) -0.0274(13) -0.0090(12) -0.0037(13) N18 0.0383(19) 0.053(2) 0.0425(19) -0.0185(16) -0.0144(15) -0.0023(17) O9 0.0403(17) 0.069(2) 0.0372(15) -0.0264(14) -0.0043(12) -0.0087(15) N20 0.0366(19) 0.052(2) 0.0397(18) -0.0210(15) -0.0152(14) 0.0021(16) C98 0.033(2) 0.045(3) 0.036(2) -0.0148(17) -0.0076(16) 0.0029(18) N22 0.0370(19) 0.043(2) 0.0476(19) -0.0264(16) -0.0111(15) 0.0011(16) O10 0.0328(15) 0.062(2) 0.0450(15) -0.0265(14) -0.0116(12) -0.0036(14) N24 0.0348(19) 0.045(2) 0.0406(18) -0.0101(15) -0.0139(15) -0.0029(16) O7 0.0407(18) 0.064(2) 0.0473(17) -0.0067(14) -0.0067(14) -0.0090(16) C100 0.034(2) 0.037(2) 0.0291(18) -0.0126(15) -0.0079(15) -0.0027(17) C99 0.036(2) 0.043(3) 0.045(2) -0.0247(18) -0.0114(17) 0.0019(18) C106 0.038(2) 0.035(2) 0.045(2) -0.0172(17) -0.0143(18) -0.0012(18) N38 0.0367(19) 0.045(2) 0.0414(18) -0.0179(15) -0.0109(15) 0.0008(16) O5 0.0519(19) 0.067(2) 0.0402(16) -0.0089(14) -0.0194(14) -0.0121(16) N30 0.0318(18) 0.054(2) 0.0490(19) -0.0221(17) -0.0142(15) 0.0029(16) C32 0.036(2) 0.062(3) 0.057(3) -0.027(2) -0.016(2) 0.008(2) C33 0.048(3) 0.046(3) 0.0269(19) -0.0080(16) -0.0144(17) -0.007(2) C34 0.033(2) 0.061(3) 0.044(2) -0.027(2) -0.0128(18) 0.000(2) C35 0.041(2) 0.042(3) 0.036(2) -0.0174(17) -0.0114(17) 0.0034(19) C36 0.033(2) 0.048(3) 0.042(2) -0.0189(18) -0.0108(17) 0.0030(19) C37 0.035(2) 0.062(3) 0.059(3) -0.038(2) -0.010(2) -0.001(2) C38 0.044(2) 0.038(3) 0.043(2) -0.0189(18) -0.0087(18) -0.0008(19) C39 0.043(2) 0.041(3) 0.043(2) -0.0158(18) -0.0176(18) -0.0021(19) C40 0.039(2) 0.046(3) 0.051(2) -0.017(2) -0.0076(19) -0.002(2) C41 0.037(2) 0.040(2) 0.034(2) -0.0163(16) -0.0069(16) -0.0022(18) N32 0.0359(19) 0.049(2) 0.0444(19) -0.0177(16) -0.0060(15) -0.0050(17) C43 0.027(2) 0.059(3) 0.047(2) -0.027(2) -0.0147(17) 0.0046(19) C44 0.038(2) 0.053(3) 0.036(2) -0.0077(18) -0.0025(17) -0.008(2) C45 0.043(2) 0.047(3) 0.058(3) -0.026(2) -0.024(2) 0.002(2) N29 0.044(2) 0.070(3) 0.0356(18) -0.0201(17) -0.0131(15) -0.0062(19) N37 0.0325(19) 0.052(2) 0.0464(19) -0.0202(16) -0.0081(15) 0.0038(16) C49 0.042(2) 0.038(2) 0.044(2) -0.0200(18) -0.0154(18) 0.0017(19) C50 0.040(2) 0.045(3) 0.034(2) -0.0062(17) -0.0079(17) -0.003(2) C51 0.041(2) 0.042(3) 0.035(2) -0.0075(17) -0.0114(17) -0.0052(19) C52 0.044(2) 0.051(3) 0.034(2) -0.0192(18) -0.0092(17) -0.007(2) C53 0.043(2) 0.034(2) 0.040(2) -0.0139(17) -0.0145(18) -0.0009(18) C54 0.062(3) 0.052(3) 0.044(2) -0.023(2) -0.026(2) 0.019(2) N39 0.0354(19) 0.062(3) 0.0379(18) -0.0226(16) -0.0117(15) 0.0070(17) C56 0.031(2) 0.043(3) 0.040(2) -0.0200(17) -0.0091(16) -0.0007(18) C57 0.040(2) 0.061(3) 0.0274(19) -0.0125(17) -0.0089(16) -0.007(2) C58 0.049(3) 0.051(3) 0.049(2) -0.027(2) 0.000(2) 0.002(2) C59 0.065(3) 0.047(3) 0.055(3) -0.020(2) -0.024(2) 0.010(2) C60 0.037(2) 0.064(3) 0.044(2) -0.030(2) -0.0116(18) 0.001(2) N35 0.040(2) 0.051(2) 0.0433(18) -0.0277(16) -0.0031(15) -0.0037(17) N33 0.0313(18) 0.064(3) 0.0481(19) -0.0339(18) -0.0074(15) 0.0001(17) C63 0.039(2) 0.044(3) 0.048(2) -0.0217(19) -0.0149(18) 0.0057(19) C64 0.046(3) 0.058(3) 0.032(2) -0.0166(19) -0.0017(17) -0.013(2) C65 0.076(3) 0.042(3) 0.056(3) -0.027(2) -0.031(2) 0.018(3) C66 0.062(3) 0.058(3) 0.050(2) -0.035(2) -0.016(2) -0.002(2) C67 0.065(3) 0.048(3) 0.048(2) -0.019(2) -0.018(2) -0.012(2) C68 0.041(2) 0.043(3) 0.036(2) -0.0066(17) -0.0099(17) -0.0057(19) C69 0.032(2) 0.060(3) 0.046(2) -0.031(2) -0.0108(18) 0.000(2) C70 0.036(2) 0.069(3) 0.034(2) -0.0149(19) -0.0095(17) -0.007(2) C71 0.067(3) 0.058(3) 0.058(3) -0.014(2) -0.017(2) 0.007(3) C72 0.077(4) 0.048(3) 0.059(3) -0.019(2) -0.010(3) -0.013(3) C73 0.060(3) 0.053(3) 0.054(3) -0.025(2) -0.013(2) -0.008(2) C74 0.048(3) 0.090(4) 0.046(3) -0.036(3) -0.013(2) 0.012(3) C75 0.045(3) 0.083(4) 0.036(2) -0.025(2) -0.0072(19) -0.009(2) C76 0.083(4) 0.048(3) 0.058(3) -0.018(2) -0.018(3) 0.011(3) C77 0.069(4) 0.065(4) 0.063(3) -0.034(3) 0.006(3) -0.009(3) C78 0.050(3) 0.060(3) 0.061(3) -0.036(2) -0.027(2) 0.016(2) C79 0.050(3) 0.060(3) 0.075(3) -0.028(3) -0.024(2) -0.001(2) C80 0.045(3) 0.085(4) 0.039(2) -0.025(2) -0.0111(19) 0.011(3) C81 0.094(4) 0.039(3) 0.050(3) -0.015(2) -0.026(3) 0.001(3) C82 0.047(3) 0.057(3) 0.049(3) -0.023(2) -0.004(2) -0.003(2) C83 0.056(3) 0.056(3) 0.066(3) -0.034(3) 0.002(2) -0.007(3) C84 0.061(3) 0.065(4) 0.051(3) -0.018(2) -0.010(2) 0.018(3) C85 0.048(3) 0.100(5) 0.040(2) -0.026(3) -0.004(2) 0.010(3) C86 0.138(6) 0.054(4) 0.051(3) -0.022(2) -0.037(3) 0.028(4) C87 0.040(2) 0.065(3) 0.051(2) -0.028(2) -0.016(2) 0.005(2) C88 0.052(3) 0.064(4) 0.053(3) -0.026(2) 0.000(2) -0.007(2) C89 0.101(5) 0.053(4) 0.090(4) -0.018(3) -0.013(4) -0.015(4) C90 0.087(4) 0.042(3) 0.053(3) -0.014(2) -0.009(3) -0.001(3) C91 0.092(4) 0.058(4) 0.084(4) -0.023(3) -0.038(3) 0.023(3) C92 0.071(4) 0.066(4) 0.068(3) -0.024(3) -0.035(3) -0.008(3) C93 0.081(4) 0.046(3) 0.061(3) -0.017(2) -0.021(3) 0.012(3) C94 0.059(3) 0.084(4) 0.056(3) -0.040(3) -0.021(2) 0.013(3) C95 0.095(5) 0.045(4) 0.128(5) -0.024(3) -0.059(4) 0.026(3) C96 0.104(6) 0.138(7) 0.122(6) -0.020(5) -0.026(5) -0.075(5) C97 0.119(6) 0.092(6) 0.126(6) -0.052(4) -0.057(5) 0.032(5) C10 0.072(3) 0.045(3) 0.045(2) -0.013(2) -0.014(2) 0.009(3) #============================================================================== _computing_data_collection PROCESS _computing_cell_refinement PROCESS _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N31 C36 1.347(5) . ? N31 C43 1.350(5) . ? N41 C105 1.376(4) . ? N41 C41 1.376(5) . ? N34 C99 1.333(4) . ? N34 C38 1.357(5) . ? N42 C105 1.353(4) . ? N42 C106 1.361(5) . ? N40 C53 1.357(5) . ? N40 C103 1.359(5) . ? N36 C100 1.337(5) . ? N36 C101 1.464(4) . ? N7 C98 1.362(4) . ? N7 C57 1.470(5) . ? O6 C104 1.214(4) . ? N9 C36 1.341(5) . ? N9 C98 1.353(5) . ? C102 C45 1.383(6) . ? C102 C39 1.397(5) . ? C101 C45 1.521(6) . ? N12 C103 1.328(5) . ? N12 C63 1.347(5) . ? C104 N18 1.382(5) . ? C104 N24 1.387(5) . ? C103 N30 1.355(5) . ? C105 O8 1.261(4) . ? N16 C100 1.364(4) . ? N16 C99 1.375(5) . ? N18 C33 1.375(4) . ? O9 C41 1.222(4) . ? N20 C98 1.341(5) . ? N20 C43 1.351(5) . ? N22 C100 1.333(4) . ? N22 C38 1.356(5) . ? O10 C106 1.241(4) . ? N24 C50 1.372(5) . ? O7 C50 1.229(5) . ? C99 N33 1.344(4) . ? C106 C56 1.524(5) . ? N38 C53 1.319(5) . ? N38 C63 1.347(5) . ? O5 C33 1.218(4) . ? N30 C70 1.450(5) . ? C32 N39 1.473(5) . ? C32 C79 1.509(6) . ? C33 C51 1.515(5) . ? C34 C60 1.395(6) . ? C34 C69 1.416(5) . ? C35 C49 1.384(5) . ? C35 C54 1.388(6) . ? C35 C70 1.517(5) . ? C36 N32 1.358(5) . ? C37 N33 1.457(5) . ? C37 C69 1.505(6) . ? C38 N35 1.353(5) . ? C39 C82 1.391(5) . ? C39 C40 1.505(6) . ? C40 N37 1.464(5) . ? C41 C56 1.518(5) . ? N32 C44 1.455(5) . ? N32 C73 1.482(5) . ? C43 N29 1.349(5) . ? C44 C71 1.497(6) . ? C45 C83 1.400(6) . ? N29 C75 1.452(5) . ? N37 C53 1.356(5) . ? C49 C52 1.405(5) . ? C50 C51 1.531(5) . ? C51 C59 1.523(6) . ? C51 C68 1.538(6) . ? C52 C67 1.378(6) . ? C52 C75 1.484(6) . ? C54 C81 1.395(7) . ? N39 C63 1.351(5) . ? N39 C87 1.455(5) . ? C56 C64 1.545(5) . ? C56 C78 1.549(6) . ? C57 C60 1.508(6) . ? C58 N35 1.481(5) . ? C58 C88 1.507(6) . ? C59 C76 1.522(6) . ? C60 C80 1.378(6) . ? N35 C66 1.475(5) . ? C64 C90 1.525(6) . ? C65 C95 1.501(6) . ? C65 C78 1.533(6) . ? C66 C94 1.505(6) . ? C67 C81 1.377(7) . ? C68 C10 1.544(6) . ? C69 C74 1.396(6) . ? C72 C93 1.510(7) . ? C73 C92 1.527(7) . ? C74 C85 1.365(7) . ? C76 C86 1.553(7) . ? C77 C83 1.384(7) . ? C77 C82 1.395(6) . ? C80 C85 1.397(6) . ? C84 C87 1.520(6) . ? C86 C97 1.521(9) . ? C89 C96 1.442(8) . ? C89 C90 1.521(7) . ? C91 C95 1.481(7) . ? C93 C10 1.501(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C36 N31 C43 113.6(3) . . ? C105 N41 C41 125.1(3) . . ? C99 N34 C38 114.2(3) . . ? C105 N42 C106 122.4(3) . . ? C53 N40 C103 112.8(3) . . ? C100 N36 C101 123.9(3) . . ? C98 N7 C57 124.6(3) . . ? C36 N9 C98 113.3(3) . . ? C45 C102 C39 121.5(4) . . ? N36 C101 C45 112.5(3) . . ? C103 N12 C63 114.2(3) . . ? O6 C104 N18 122.0(4) . . ? O6 C104 N24 121.3(4) . . ? N18 C104 N24 116.7(3) . . ? N12 C103 N30 117.8(3) . . ? N12 C103 N40 126.3(4) . . ? N30 C103 N40 115.9(3) . . ? O8 C105 N42 121.5(3) . . ? O8 C105 N41 118.3(3) . . ? N42 C105 N41 120.2(3) . . ? C100 N16 C99 116.0(3) . . ? C33 N18 C104 125.6(3) . . ? C98 N20 C43 113.2(3) . . ? N20 C98 N9 127.0(3) . . ? N20 C98 N7 115.7(4) . . ? N9 C98 N7 117.3(4) . . ? C100 N22 C38 115.0(3) . . ? C50 N24 C104 125.7(3) . . ? N22 C100 N36 120.3(3) . . ? N22 C100 N16 123.9(3) . . ? N36 C100 N16 115.8(3) . . ? N34 C99 N33 119.4(4) . . ? N34 C99 N16 124.3(3) . . ? N33 C99 N16 116.2(3) . . ? O10 C106 N42 120.1(3) . . ? O10 C106 C56 118.9(3) . . ? N42 C106 C56 120.9(3) . . ? C53 N38 C63 114.6(3) . . ? C103 N30 C70 124.3(3) . . ? N39 C32 C79 114.4(4) . . ? O5 C33 N18 120.1(4) . . ? O5 C33 C51 120.6(3) . . ? N18 C33 C51 119.3(3) . . ? C60 C34 C69 121.9(4) . . ? C49 C35 C54 118.6(4) . . ? C49 C35 C70 119.8(4) . . ? C54 C35 C70 121.6(4) . . ? N9 C36 N31 126.6(4) . . ? N9 C36 N32 117.0(4) . . ? N31 C36 N32 116.4(3) . . ? N33 C37 C69 114.3(4) . . ? N35 C38 N22 117.1(4) . . ? N35 C38 N34 116.5(4) . . ? N22 C38 N34 126.4(3) . . ? C82 C39 C102 118.3(4) . . ? C82 C39 C40 119.2(4) . . ? C102 C39 C40 122.5(4) . . ? N37 C40 C39 114.7(4) . . ? O9 C41 N41 120.4(3) . . ? O9 C41 C56 122.3(3) . . ? N41 C41 C56 117.3(3) . . ? C36 N32 C44 121.3(3) . . ? C36 N32 C73 119.4(3) . . ? C44 N32 C73 118.8(3) . . ? N29 C43 N31 117.8(4) . . ? N29 C43 N20 115.9(4) . . ? N31 C43 N20 126.3(4) . . ? N32 C44 C71 112.5(4) . . ? C102 C45 C83 119.0(4) . . ? C102 C45 C101 120.7(4) . . ? C83 C45 C101 120.3(4) . . ? C43 N29 C75 125.8(4) . . ? C53 N37 C40 123.7(4) . . ? C35 C49 C52 122.1(4) . . ? O7 C50 N24 120.4(4) . . ? O7 C50 C51 120.8(3) . . ? N24 C50 C51 118.8(3) . . ? C33 C51 C59 109.6(4) . . ? C33 C51 C50 113.7(3) . . ? C59 C51 C50 106.6(4) . . ? C33 C51 C68 109.2(4) . . ? C59 C51 C68 109.5(3) . . ? C50 C51 C68 108.0(3) . . ? C67 C52 C49 117.8(4) . . ? C67 C52 C75 123.6(4) . . ? C49 C52 C75 118.6(4) . . ? N38 C53 N37 117.1(4) . . ? N38 C53 N40 126.5(4) . . ? N37 C53 N40 116.4(4) . . ? C35 C54 C81 120.0(4) . . ? C63 N39 C87 120.8(3) . . ? C63 N39 C32 120.8(3) . . ? C87 N39 C32 117.5(3) . . ? C41 C56 C106 113.9(3) . . ? C41 C56 C64 109.6(3) . . ? C106 C56 C64 108.4(3) . . ? C41 C56 C78 107.4(3) . . ? C106 C56 C78 108.0(3) . . ? C64 C56 C78 109.4(3) . . ? N7 C57 C60 110.8(3) . . ? N35 C58 C88 112.6(4) . . ? C76 C59 C51 115.7(4) . . ? C80 C60 C34 118.9(4) . . ? C80 C60 C57 122.2(4) . . ? C34 C60 C57 118.9(4) . . ? C38 N35 C66 119.8(3) . . ? C38 N35 C58 120.6(3) . . ? C66 N35 C58 119.6(3) . . ? C99 N33 C37 123.3(3) . . ? N12 C63 N38 125.4(4) . . ? N12 C63 N39 118.3(4) . . ? N38 C63 N39 116.3(4) . . ? C90 C64 C56 114.4(4) . . ? C95 C65 C78 111.1(4) . . ? N35 C66 C94 113.0(4) . . ? C81 C67 C52 121.3(4) . . ? C51 C68 C10 113.7(3) . . ? C74 C69 C34 117.2(4) . . ? C74 C69 C37 122.1(4) . . ? C34 C69 C37 120.6(4) . . ? N30 C70 C35 110.9(3) . . ? N32 C73 C92 112.3(4) . . ? C85 C74 C69 120.9(4) . . ? N29 C75 C52 112.4(3) . . ? C59 C76 C86 111.7(4) . . ? C83 C77 C82 119.2(5) . . ? C65 C78 C56 115.2(4) . . ? C60 C80 C85 119.8(5) . . ? C67 C81 C54 120.2(5) . . ? C39 C82 C77 121.3(5) . . ? C77 C83 C45 120.7(5) . . ? C74 C85 C80 121.3(4) . . ? C97 C86 C76 112.0(5) . . ? N39 C87 C84 112.8(4) . . ? C96 C89 C90 114.9(5) . . ? C89 C90 C64 115.1(5) . . ? C10 C93 C72 111.5(4) . . ? C91 C95 C65 113.0(5) . . ? C93 C10 C68 112.4(4) . . ? #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================