# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Juan Granja' _publ_contact_author_address ; Organic Chemistry University of Santiago Campus Sur Santiago de Compostela 15782 SPAIN ; _publ_contact_author_email QOJUANGG@USC.ES _publ_section_title ; New ?,?-cyclic peptides for large-diameter self-assembling peptide nanotubes ; loop_ _publ_author_name 'Juan Granja' 'Roberto J. Brea' 'Luis Castedo' data_jg05ro2n _database_code_depnum_ccdc_archive 'CCDC 635857' _audit_creation_date 2005-04-27T19:41:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C52 H88 N8 O8, 4(C2 H2 Cl2 O2)' _chemical_formula_sum 'C60 H96 Cl8 N8 O16' _chemical_formula_weight 1469.05 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 4' _symmetry_space_group_name_Hall 'I 4' _symmetry_Int_Tables_number 79 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' _cell_length_a 23.6648(9) _cell_length_b 23.6648(9) _cell_length_c 16.5051(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 9243.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2974 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 22.81 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.35 _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.056 _exptl_crystal_F_000 3104 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.709 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_process_details ; SADABS Sheldrick,G.M. (1997). University of Gottingen, Germany. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0409 _diffrn_reflns_number 34689 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 24.79 _diffrn_reflns_theta_full 24.79 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 7868 _reflns_number_gt 5748 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART (Bruker AXS)' _computing_cell_refinement 'SAINT+ (Bruker AXS)' _computing_data_reduction 'SAINT+ (Bruker AXS)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.039 1104.5 354.9 2 0.500 0.500 0.009 1104.5 354.9 _platon_squeeze_details ; ? ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7868 _refine_ls_number_parameters 424 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.2194 _refine_ls_wR_factor_gt 0.2042 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(10) _refine_diff_density_max 0.926 _refine_diff_density_min -0.62 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N101 N -0.07103(14) 0.25430(14) 0.0339(2) 0.0340(7) Uani 1 1 d . . . H101 H -0.075 0.2501 0.0866 0.041 Uiso 1 1 calc R . . C102 C -0.02219(18) 0.28550(18) 0.0046(3) 0.0366(9) Uani 1 1 d . . . H102 H -0.0203 0.2841 -0.0559 0.044 Uiso 1 1 calc R . . C103 C -0.0255(2) 0.34735(18) 0.0342(3) 0.0438(10) Uani 1 1 d . . . H10A H -0.0249 0.3475 0.0942 0.053 Uiso 1 1 calc R . . H10B H 0.0085 0.3677 0.0152 0.053 Uiso 1 1 calc R . . C104 C -0.0784(2) 0.3799(2) 0.0054(4) 0.0610(15) Uani 1 1 d . . . H104 H -0.1119 0.355 0.0149 0.073 Uiso 1 1 calc R . . C105 C -0.0760(3) 0.3925(3) -0.0820(4) 0.0691(16) Uani 1 1 d . . . H10C H -0.1117 0.4096 -0.0991 0.104 Uiso 1 1 calc R . . H10D H -0.0698 0.3574 -0.1123 0.104 Uiso 1 1 calc R . . H10E H -0.0449 0.4187 -0.0927 0.104 Uiso 1 1 calc R . . C106 C -0.0868(4) 0.4326(3) 0.0533(4) 0.088(2) Uani 1 1 d . . . H10F H -0.0512 0.4537 0.0557 0.132 Uiso 1 1 calc R . . H10G H -0.0989 0.4228 0.1083 0.132 Uiso 1 1 calc R . . H10H H -0.1158 0.4559 0.0273 0.132 Uiso 1 1 calc R . . C110 C 0.03027(18) 0.25819(19) 0.0417(3) 0.0377(9) Uani 1 1 d . . . O111 O 0.02817(14) 0.24551(17) 0.11322(18) 0.0537(9) Uani 1 1 d . . . N112 N 0.07611(15) 0.25056(15) -0.0036(2) 0.0389(8) Uani 1 1 d . . . C113 C 0.0782(2) 0.2645(2) -0.0912(3) 0.0510(12) Uani 1 1 d . . . H11A H 0.0545 0.2378 -0.1214 0.076 Uiso 1 1 calc R . . H11B H 0.1173 0.2618 -0.1104 0.076 Uiso 1 1 calc R . . H11C H 0.0643 0.303 -0.0996 0.076 Uiso 1 1 calc R . . C114 C 0.12507(17) 0.22276(19) 0.0319(3) 0.0389(9) Uani 1 1 d . . . H114 H 0.1154 0.2136 0.0894 0.047 Uiso 1 1 calc R . . C115 C 0.1410(2) 0.1681(2) -0.0093(4) 0.0607(14) Uani 1 1 d . . . H11D H 0.143 0.1726 -0.0689 0.073 Uiso 1 1 calc R . . H11E H 0.1141 0.1374 0.0041 0.073 Uiso 1 1 calc R . . C116 C 0.19959(19) 0.1568(2) 0.0273(3) 0.0444(11) Uani 1 1 d . . . H116 H 0.1945 0.1459 0.0854 0.053 Uiso 1 1 calc R . . C117 C 0.2271(2) 0.2136(3) 0.0247(6) 0.094(3) Uani 1 1 d . . . H11F H 0.2474 0.2188 -0.0272 0.112 Uiso 1 1 calc R . . H11G H 0.2544 0.2176 0.0697 0.112 Uiso 1 1 calc R . . C118 C 0.1793(2) 0.2575(2) 0.0329(4) 0.0593(13) Uani 1 1 d . . . H11H H 0.1828 0.2788 0.0843 0.071 Uiso 1 1 calc R . . H11I H 0.18 0.2845 -0.0129 0.071 Uiso 1 1 calc R . . C120 C 0.23149(19) 0.1105(2) -0.0146(3) 0.0403(10) Uani 1 1 d . . . O121 O 0.2366(2) 0.1107(2) -0.0895(2) 0.0754(13) Uani 1 1 d D . . N201 N 0.26418(15) 0.00224(14) 0.2831(2) 0.0338(7) Uani 1 1 d . . . H201 H 0.2603 -0.0023 0.2305 0.041 Uiso 1 1 calc R . . C202 C 0.27616(17) 0.05808(17) 0.3143(2) 0.0311(8) Uani 1 1 d . . . H202 H 0.2705 0.0588 0.3743 0.037 Uiso 1 1 calc R . . C203 C 0.33624(18) 0.07742(19) 0.2934(3) 0.0400(10) Uani 1 1 d . . . H20A H 0.3418 0.0737 0.2342 0.048 Uiso 1 1 calc R . . H20B H 0.3398 0.118 0.3071 0.048 Uiso 1 1 calc R . . C204 C 0.3825(2) 0.0457(2) 0.3357(3) 0.0547(12) Uani 1 1 d . . . H204 H 0.3753 0.0043 0.3297 0.066 Uiso 1 1 calc R . . C205 C 0.3845(3) 0.0603(3) 0.4273(4) 0.0758(19) Uani 1 1 d . . . H20C H 0.3924 0.1007 0.434 0.114 Uiso 1 1 calc R . . H20D H 0.4143 0.0382 0.4536 0.114 Uiso 1 1 calc R . . H20E H 0.3479 0.0513 0.4521 0.114 Uiso 1 1 calc R . . C206 C 0.4392(2) 0.0601(3) 0.2939(5) 0.0781(19) Uani 1 1 d . . . H20F H 0.4401 0.0431 0.2398 0.117 Uiso 1 1 calc R . . H20G H 0.4705 0.0451 0.3263 0.117 Uiso 1 1 calc R . . H20H H 0.443 0.1012 0.2893 0.117 Uiso 1 1 calc R . . C210 C 0.23506(16) 0.09951(16) 0.2730(2) 0.0311(8) Uani 1 1 d . . . O211 O 0.22327(14) 0.09320(13) 0.20234(19) 0.0478(8) Uani 1 1 d . . . N212 N 0.21562(15) 0.14271(16) 0.3182(2) 0.0402(8) Uani 1 1 d . . . C213 C 0.2265(3) 0.1467(3) 0.4069(3) 0.0589(14) Uani 1 1 d . . . H21A H 0.205 0.1173 0.4351 0.088 Uiso 1 1 calc R . . H21B H 0.2146 0.184 0.4265 0.088 Uiso 1 1 calc R . . H21C H 0.2669 0.1416 0.4173 0.088 Uiso 1 1 calc R . . C214 C 0.17871(19) 0.1859(2) 0.2805(3) 0.0447(10) Uani 1 1 d . . . H214 H 0.1761 0.1777 0.2212 0.054 Uiso 1 1 calc R . . C215 C 0.11847(19) 0.18531(19) 0.3160(3) 0.0476(11) Uani 1 1 d . . . H21D H 0.0951 0.1551 0.2916 0.057 Uiso 1 1 calc R . . H21E H 0.119 0.1807 0.3756 0.057 Uiso 1 1 calc R . . C216 C 0.09781(19) 0.2436(2) 0.2915(3) 0.0433(10) Uani 1 1 d . . . H216 H 0.0928 0.2448 0.2314 0.052 Uiso 1 1 calc R . . C217 C 0.1472(2) 0.2809(2) 0.3150(5) 0.0656(15) Uani 1 1 d . . . H21F H 0.1469 0.2888 0.3739 0.079 Uiso 1 1 calc R . . H21G H 0.1458 0.3173 0.2852 0.079 Uiso 1 1 calc R . . C218 C 0.1998(2) 0.2470(2) 0.2913(3) 0.0509(11) Uani 1 1 d . . . H21H H 0.2288 0.2491 0.3344 0.061 Uiso 1 1 calc R . . H21I H 0.2163 0.2615 0.2402 0.061 Uiso 1 1 calc R . . C220 C 0.04279(18) 0.25886(19) 0.3316(3) 0.0398(10) Uani 1 1 d . . . O221 O 0.03794(14) 0.26635(16) 0.40583(19) 0.0528(9) Uani 1 1 d D . . O11 O 0.27426(16) 0.10213(14) -0.2326(2) 0.0541(9) Uani 1 1 d . . . H11 H 0.2696 0.0988 -0.1824 0.081 Uiso 1 1 calc RD . . O12 O 0.2775(4) 0.0087(2) -0.2313(3) 0.139(3) Uani 1 1 d . . . C13 C 0.2841(3) 0.0517(2) -0.2648(3) 0.0635(15) Uani 1 1 d . . . C14 C 0.3103(3) 0.0542(3) -0.3451(3) 0.0670(16) Uani 1 1 d . . . H14 H 0.3123 0.0146 -0.3661 0.08 Uiso 1 1 calc R . . Cl15 Cl 0.37981(9) 0.08042(13) -0.34165(13) 0.1162(9) Uani 1 1 d . . . Cl16 Cl 0.26921(9) 0.09298(8) -0.41281(10) 0.0900(6) Uani 1 1 d . . . O21 O 0.06574(19) 0.2556(2) 0.5562(2) 0.0790(13) Uani 1 1 d . . . H21 H 0.0671 0.2645 0.5069 0.118 Uiso 1 1 calc RD . . O22 O 0.1448(2) 0.2093(3) 0.5344(3) 0.0966(17) Uani 1 1 d . . . C23 C 0.1105(2) 0.2337(3) 0.5761(3) 0.0560(14) Uani 1 1 d . . . C24 C 0.1182(3) 0.2337(3) 0.6664(4) 0.0734(18) Uani 1 1 d . . . H24 H 0.0801 0.2293 0.6919 0.088 Uiso 1 1 calc R . . Cl25 Cl 0.16262(10) 0.18092(9) 0.70573(13) 0.1013(7) Uani 1 1 d . . . Cl26 Cl 0.14493(16) 0.29736(9) 0.69519(15) 0.1544(15) Uani 1 1 d . . . 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 N101 0.0372(18) 0.0356(17) 0.0293(17) -0.0003(14) 0.0032(14) -0.0035(14) C102 0.040(2) 0.036(2) 0.033(2) 0.0041(17) 0.0069(18) 0.0003(18) C103 0.053(3) 0.034(2) 0.045(3) 0.0018(19) -0.002(2) 0.0024(19) C104 0.045(3) 0.038(3) 0.101(5) 0.017(3) 0.022(3) 0.001(2) C105 0.068(4) 0.054(3) 0.085(5) 0.008(3) -0.018(3) 0.009(3) C106 0.135(7) 0.065(4) 0.064(4) 0.001(3) 0.014(4) 0.035(4) C110 0.038(2) 0.045(2) 0.031(2) -0.0008(18) 0.0046(18) -0.0007(18) O111 0.0462(19) 0.087(3) 0.0282(17) 0.0138(16) 0.0058(13) 0.0019(17) N112 0.0365(19) 0.0374(19) 0.043(2) 0.0068(15) -0.0002(16) 0.0008(15) C113 0.049(3) 0.074(3) 0.030(2) 0.014(2) 0.006(2) 0.013(2) C114 0.033(2) 0.050(3) 0.033(2) 0.0082(19) -0.0010(17) 0.0031(18) C115 0.043(3) 0.054(3) 0.085(4) -0.005(3) -0.002(3) 0.008(2) C116 0.042(2) 0.059(3) 0.032(2) 0.003(2) 0.0064(19) 0.007(2) C117 0.035(3) 0.069(4) 0.177(8) -0.009(5) -0.002(4) -0.005(3) C118 0.046(3) 0.047(3) 0.085(4) -0.002(3) -0.008(3) -0.009(2) C120 0.043(2) 0.046(3) 0.032(2) 0.0085(18) 0.0090(18) 0.007(2) O121 0.087(3) 0.096(3) 0.043(2) 0.019(2) 0.0201(19) 0.047(2) N201 0.0434(19) 0.0332(18) 0.0247(16) 0.0011(13) 0.0010(14) -0.0063(14) C202 0.036(2) 0.040(2) 0.0178(18) 0.0032(15) -0.0030(15) -0.0006(17) C203 0.037(2) 0.044(2) 0.039(2) 0.0023(19) 0.0005(18) -0.0086(18) C204 0.047(3) 0.054(3) 0.063(3) 0.008(2) -0.012(2) -0.007(2) C205 0.069(4) 0.092(5) 0.066(4) 0.019(3) -0.037(3) -0.013(3) C206 0.037(3) 0.076(4) 0.121(6) 0.003(4) -0.006(3) 0.007(3) C210 0.033(2) 0.032(2) 0.028(2) -0.0039(16) -0.0004(16) 0.0007(16) O211 0.0597(19) 0.0504(18) 0.0332(17) 0.0004(14) -0.0092(14) 0.0198(15) N212 0.0350(19) 0.054(2) 0.0315(19) 0.0001(16) -0.0052(15) 0.0093(16) C213 0.080(4) 0.073(4) 0.024(2) -0.013(2) -0.011(2) 0.023(3) C214 0.040(2) 0.056(3) 0.038(2) -0.004(2) -0.0051(19) 0.010(2) C215 0.037(2) 0.042(3) 0.064(3) -0.011(2) 0.003(2) -0.0033(19) C216 0.044(2) 0.056(3) 0.031(2) 0.0006(19) -0.0052(18) 0.011(2) C217 0.049(3) 0.047(3) 0.101(5) 0.008(3) 0.000(3) 0.002(2) C218 0.040(3) 0.051(3) 0.061(3) 0.000(2) -0.005(2) -0.003(2) C220 0.037(2) 0.040(2) 0.042(3) -0.0020(19) 0.0004(19) 0.0092(18) O221 0.0481(19) 0.078(2) 0.0317(17) -0.0113(16) -0.0087(14) 0.0141(17) O11 0.078(2) 0.053(2) 0.0310(17) 0.0021(14) 0.0060(16) -0.0106(17) O12 0.302(10) 0.054(3) 0.061(3) 0.014(2) 0.048(4) 0.006(4) C13 0.094(4) 0.055(3) 0.041(3) -0.003(3) 0.008(3) 0.009(3) C14 0.096(5) 0.059(3) 0.045(3) 0.001(2) 0.006(3) -0.006(3) Cl15 0.0857(13) 0.187(2) 0.0756(12) -0.0427(14) 0.0215(10) -0.0112(14) Cl16 0.1245(15) 0.1047(13) 0.0408(7) 0.0161(8) -0.0072(9) 0.0131(11) O21 0.075(3) 0.124(4) 0.038(2) -0.012(2) -0.0023(19) 0.029(3) O22 0.075(3) 0.155(5) 0.060(3) -0.015(3) -0.004(2) 0.040(3) C23 0.052(3) 0.080(4) 0.036(3) -0.017(2) -0.006(2) -0.012(3) C24 0.062(4) 0.099(5) 0.059(4) -0.021(3) -0.016(3) 0.015(3) Cl25 0.1318(17) 0.0889(12) 0.0832(12) 0.0069(9) -0.0378(12) 0.0063(11) Cl26 0.278(4) 0.0758(12) 0.1094(17) -0.0350(12) -0.116(2) 0.0244(16) #----------------------------------------------------------------------------# # 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 N101 C120 1.343(6) 3 ? N101 C102 1.454(6) . ? N101 H101 0.88 . ? C102 C110 1.527(6) . ? C102 C103 1.545(6) . ? C102 H102 1 . ? C103 C104 1.543(7) . ? C103 H10A 0.99 . ? C103 H10B 0.99 . ? C104 C105 1.475(10) . ? C104 C106 1.490(9) . ? C104 H104 1 . ? C105 H10C 0.98 . ? C105 H10D 0.98 . ? C105 H10E 0.98 . ? C106 H10F 0.98 . ? C106 H10G 0.98 . ? C106 H10H 0.98 . ? C110 O111 1.220(5) . ? C110 N112 1.330(6) . ? N112 C114 1.456(6) . ? N112 C113 1.483(6) . ? C113 H11A 0.98 . ? C113 H11B 0.98 . ? C113 H11C 0.98 . ? C114 C115 1.510(7) . ? C114 C118 1.523(7) . ? C114 H114 1 . ? C115 C116 1.536(7) . ? C115 H11D 0.99 . ? C115 H11E 0.99 . ? C116 C117 1.493(8) . ? C116 C120 1.500(7) . ? C116 H116 1 . ? C117 C118 1.542(8) . ? C117 H11F 0.99 . ? C117 H11G 0.99 . ? C118 H11H 0.99 . ? C118 H11I 0.99 . ? C120 O121 1.243(6) . ? C120 N101 1.343(6) 4 ? N201 C220 1.339(6) 4 ? N201 C202 1.446(5) . ? N201 H201 0.88 . ? C202 C203 1.533(6) . ? C202 C210 1.540(6) . ? C202 H202 1 . ? C203 C204 1.500(7) . ? C203 H20A 0.99 . ? C203 H20B 0.99 . ? C204 C206 1.546(8) . ? C204 C205 1.552(9) . ? C204 H204 1 . ? C205 H20C 0.98 . ? C205 H20D 0.98 . ? C205 H20E 0.98 . ? C206 H20F 0.98 . ? C206 H20G 0.98 . ? C206 H20H 0.98 . ? C210 O211 1.208(5) . ? C210 N212 1.347(5) . ? N212 C214 1.481(6) . ? N212 C213 1.489(6) . ? C213 H21A 0.98 . ? C213 H21B 0.98 . ? C213 H21C 0.98 . ? C214 C218 1.541(7) . ? C214 C215 1.542(7) . ? C214 H214 1 . ? C215 C216 1.518(7) . ? C215 H21D 0.99 . ? C215 H21E 0.99 . ? C216 C220 1.505(6) . ? C216 C217 1.515(8) . ? C216 H216 1 . ? C217 C218 1.533(7) . ? C217 H21F 0.99 . ? C217 H21G 0.99 . ? C218 H21H 0.99 . ? C218 H21I 0.99 . ? C220 O221 1.243(6) . ? C220 N201 1.339(6) 3 ? O11 C13 1.327(7) . ? O11 H11 0.84 . ? O12 C13 1.167(7) . ? C13 C14 1.464(8) . ? C14 Cl16 1.743(7) . ? C14 Cl15 1.760(7) . ? C14 H14 1 . ? O21 C23 1.225(7) . ? O21 H21 0.84 . ? O22 C23 1.211(7) . ? C23 C24 1.501(8) . ? C24 Cl26 1.702(7) . ? C24 Cl25 1.757(7) . ? C24 H24 1 . ? 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 C120 N101 C102 123.9(4) 3 . ? C120 N101 H101 118 3 . ? C102 N101 H101 118 . . ? N101 C102 C110 107.3(3) . . ? N101 C102 C103 109.6(3) . . ? C110 C102 C103 108.4(4) . . ? N101 C102 H102 110.5 . . ? C110 C102 H102 110.5 . . ? C103 C102 H102 110.5 . . ? C104 C103 C102 114.6(4) . . ? C104 C103 H10A 108.6 . . ? C102 C103 H10A 108.6 . . ? C104 C103 H10B 108.6 . . ? C102 C103 H10B 108.6 . . ? H10A C103 H10B 107.6 . . ? C105 C104 C106 110.8(5) . . ? C105 C104 C103 111.8(5) . . ? C106 C104 C103 111.3(6) . . ? C105 C104 H104 107.6 . . ? C106 C104 H104 107.6 . . ? C103 C104 H104 107.6 . . ? C104 C105 H10C 109.5 . . ? C104 C105 H10D 109.5 . . ? H10C C105 H10D 109.5 . . ? C104 C105 H10E 109.5 . . ? H10C C105 H10E 109.5 . . ? H10D C105 H10E 109.5 . . ? C104 C106 H10F 109.5 . . ? C104 C106 H10G 109.5 . . ? H10F C106 H10G 109.5 . . ? C104 C106 H10H 109.5 . . ? H10F C106 H10H 109.5 . . ? H10G C106 H10H 109.5 . . ? O111 C110 N112 123.0(4) . . ? O111 C110 C102 117.3(4) . . ? N112 C110 C102 119.7(4) . . ? C110 N112 C114 119.0(4) . . ? C110 N112 C113 123.0(4) . . ? C114 N112 C113 117.8(4) . . ? N112 C113 H11A 109.5 . . ? N112 C113 H11B 109.5 . . ? H11A C113 H11B 109.5 . . ? N112 C113 H11C 109.5 . . ? H11A C113 H11C 109.5 . . ? H11B C113 H11C 109.5 . . ? N112 C114 C115 113.9(4) . . ? N112 C114 C118 115.5(4) . . ? C115 C114 C118 104.9(4) . . ? N112 C114 H114 107.4 . . ? C115 C114 H114 107.4 . . ? C118 C114 H114 107.4 . . ? C114 C115 C116 101.3(4) . . ? C114 C115 H11D 111.5 . . ? C116 C115 H11D 111.5 . . ? C114 C115 H11E 111.5 . . ? C116 C115 H11E 111.5 . . ? H11D C115 H11E 109.3 . . ? C117 C116 C120 115.2(4) . . ? C117 C116 C115 103.0(4) . . ? C120 C116 C115 113.5(4) . . ? C117 C116 H116 108.3 . . ? C120 C116 H116 108.3 . . ? C115 C116 H116 108.3 . . ? C116 C117 C118 106.5(4) . . ? C116 C117 H11F 110.4 . . ? C118 C117 H11F 110.4 . . ? C116 C117 H11G 110.4 . . ? C118 C117 H11G 110.4 . . ? H11F C117 H11G 108.6 . . ? C114 C118 C117 104.7(4) . . ? C114 C118 H11H 110.8 . . ? C117 C118 H11H 110.8 . . ? C114 C118 H11I 110.8 . . ? C117 C118 H11I 110.8 . . ? H11H C118 H11I 108.9 . . ? O121 C120 N101 123.8(4) . 4 ? O121 C120 C116 120.3(4) . . ? N101 C120 C116 115.8(4) 4 . ? C220 N201 C202 122.2(3) 4 . ? C220 N201 H201 118.9 4 . ? C202 N201 H201 118.9 . . ? N201 C202 C203 112.0(3) . . ? N201 C202 C210 107.5(3) . . ? C203 C202 C210 107.2(3) . . ? N201 C202 H202 110 . . ? C203 C202 H202 110 . . ? C210 C202 H202 110 . . ? C204 C203 C202 115.1(4) . . ? C204 C203 H20A 108.5 . . ? C202 C203 H20A 108.5 . . ? C204 C203 H20B 108.5 . . ? C202 C203 H20B 108.5 . . ? H20A C203 H20B 107.5 . . ? C203 C204 C206 108.5(5) . . ? C203 C204 C205 111.3(5) . . ? C206 C204 C205 111.1(5) . . ? C203 C204 H204 108.7 . . ? C206 C204 H204 108.7 . . ? C205 C204 H204 108.7 . . ? C204 C205 H20C 109.5 . . ? C204 C205 H20D 109.5 . . ? H20C C205 H20D 109.5 . . ? C204 C205 H20E 109.5 . . ? H20C C205 H20E 109.5 . . ? H20D C205 H20E 109.5 . . ? C204 C206 H20F 109.5 . . ? C204 C206 H20G 109.5 . . ? H20F C206 H20G 109.5 . . ? C204 C206 H20H 109.5 . . ? H20F C206 H20H 109.5 . . ? H20G C206 H20H 109.5 . . ? O211 C210 N212 123.3(4) . . ? O211 C210 C202 119.6(3) . . ? N212 C210 C202 117.0(3) . . ? C210 N212 C214 119.5(3) . . ? C210 N212 C213 122.3(4) . . ? C214 N212 C213 118.1(4) . . ? N212 C213 H21A 109.5 . . ? N212 C213 H21B 109.5 . . ? H21A C213 H21B 109.5 . . ? N212 C213 H21C 109.5 . . ? H21A C213 H21C 109.5 . . ? H21B C213 H21C 109.5 . . ? N212 C214 C218 114.1(4) . . ? N212 C214 C215 112.3(4) . . ? C218 C214 C215 105.3(4) . . ? N212 C214 H214 108.3 . . ? C218 C214 H214 108.3 . . ? C215 C214 H214 108.3 . . ? C216 C215 C214 100.9(4) . . ? C216 C215 H21D 111.6 . . ? C214 C215 H21D 111.6 . . ? C216 C215 H21E 111.6 . . ? C214 C215 H21E 111.6 . . ? H21D C215 H21E 109.4 . . ? C220 C216 C217 114.5(4) . . ? C220 C216 C215 112.3(4) . . ? C217 C216 C215 102.3(4) . . ? C220 C216 H216 109.1 . . ? C217 C216 H216 109.1 . . ? C215 C216 H216 109.1 . . ? C216 C217 C218 104.8(4) . . ? C216 C217 H21F 110.8 . . ? C218 C217 H21F 110.8 . . ? C216 C217 H21G 110.8 . . ? C218 C217 H21G 110.8 . . ? H21F C217 H21G 108.9 . . ? C217 C218 C214 104.9(4) . . ? C217 C218 H21H 110.8 . . ? C214 C218 H21H 110.8 . . ? C217 C218 H21I 110.8 . . ? C214 C218 H21I 110.8 . . ? H21H C218 H21I 108.8 . . ? O221 C220 N201 120.2(4) . 3 ? O221 C220 C216 123.2(4) . . ? N201 C220 C216 116.6(4) 3 . ? C13 O11 H11 109.5 . . ? O12 C13 O11 124.8(5) . . ? O12 C13 C14 121.3(6) . . ? O11 C13 C14 113.6(5) . . ? C13 C14 Cl16 111.5(5) . . ? C13 C14 Cl15 112.3(5) . . ? Cl16 C14 Cl15 110.8(3) . . ? C13 C14 H14 107.3 . . ? Cl16 C14 H14 107.3 . . ? Cl15 C14 H14 107.3 . . ? C23 O21 H21 109.5 . . ? O22 C23 O21 128.9(5) . . ? O22 C23 C24 119.0(6) . . ? O21 C23 C24 111.8(5) . . ? C23 C24 Cl26 108.8(5) . . ? C23 C24 Cl25 116.0(5) . . ? Cl26 C24 Cl25 107.7(3) . . ? C23 C24 H24 108 . . ? Cl26 C24 H24 108 . . ? Cl25 C24 H24 108 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C120 N101 C102 C110 -126.2(4) 3 . . . ? C120 N101 C102 C103 116.3(4) 3 . . . ? N101 C102 C103 C104 -60.1(5) . . . . ? C110 C102 C103 C104 -176.9(4) . . . . ? C102 C103 C104 C105 -71.0(6) . . . . ? C102 C103 C104 C106 164.6(5) . . . . ? N101 C102 C110 O111 -43.4(5) . . . . ? C103 C102 C110 O111 74.9(5) . . . . ? N101 C102 C110 N112 138.3(4) . . . . ? C103 C102 C110 N112 -103.5(5) . . . . ? O111 C110 N112 C114 3.8(7) . . . . ? C102 C110 N112 C114 -178.0(4) . . . . ? O111 C110 N112 C113 178.2(5) . . . . ? C102 C110 N112 C113 -3.5(6) . . . . ? C110 N112 C114 C115 118.1(5) . . . . ? C113 N112 C114 C115 -56.6(6) . . . . ? C110 N112 C114 C118 -120.3(5) . . . . ? C113 N112 C114 C118 64.9(6) . . . . ? N112 C114 C115 C116 167.7(4) . . . . ? C118 C114 C115 C116 40.4(5) . . . . ? C114 C115 C116 C117 -43.4(6) . . . . ? C114 C115 C116 C120 -168.6(4) . . . . ? C120 C116 C117 C118 154.2(5) . . . . ? C115 C116 C117 C118 30.0(8) . . . . ? N112 C114 C118 C117 -148.5(5) . . . . ? C115 C114 C118 C117 -22.2(7) . . . . ? C116 C117 C118 C114 -5.2(8) . . . . ? C117 C116 C120 O121 -68.2(7) . . . . ? C115 C116 C120 O121 50.2(7) . . . . ? C117 C116 C120 N101 110.3(6) . . . 4 ? C115 C116 C120 N101 -131.2(5) . . . 4 ? C220 N201 C202 C203 109.3(4) 4 . . . ? C220 N201 C202 C210 -133.1(4) 4 . . . ? N201 C202 C203 C204 -68.5(5) . . . . ? C210 C202 C203 C204 173.8(4) . . . . ? C202 C203 C204 C206 166.8(5) . . . . ? C202 C203 C204 C205 -70.7(6) . . . . ? N201 C202 C210 O211 -38.3(5) . . . . ? C203 C202 C210 O211 82.2(5) . . . . ? N201 C202 C210 N212 144.0(3) . . . . ? C203 C202 C210 N212 -95.4(4) . . . . ? O211 C210 N212 C214 -1.2(6) . . . . ? C202 C210 N212 C214 176.3(4) . . . . ? O211 C210 N212 C213 174.3(5) . . . . ? C202 C210 N212 C213 -8.1(6) . . . . ? C210 N212 C214 C218 -125.8(4) . . . . ? C213 N212 C214 C218 58.4(6) . . . . ? C210 N212 C214 C215 114.5(4) . . . . ? C213 N212 C214 C215 -61.3(6) . . . . ? N212 C214 C215 C216 160.6(4) . . . . ? C218 C214 C215 C216 35.9(5) . . . . ? C214 C215 C216 C220 -169.7(4) . . . . ? C214 C215 C216 C217 -46.4(5) . . . . ? C220 C216 C217 C218 161.7(4) . . . . ? C215 C216 C217 C218 39.9(6) . . . . ? C216 C217 C218 C214 -17.0(6) . . . . ? N212 C214 C218 C217 -135.4(5) . . . . ? C215 C214 C218 C217 -11.8(6) . . . . ? C217 C216 C220 O221 -49.9(7) . . . . ? C215 C216 C220 O221 66.3(6) . . . . ? C217 C216 C220 N201 130.2(5) . . . 3 ? C215 C216 C220 N201 -113.6(4) . . . 3 ? O12 C13 C14 Cl16 128.7(8) . . . . ? O11 C13 C14 Cl16 -57.2(7) . . . . ? O12 C13 C14 Cl15 -106.1(8) . . . . ? O11 C13 C14 Cl15 67.9(6) . . . . ? O22 C23 C24 Cl26 102.4(6) . . . . ? O21 C23 C24 Cl26 -83.7(6) . . . . ? O22 C23 C24 Cl25 -19.1(8) . . . . ? O21 C23 C24 Cl25 154.8(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N101 H101 O211 0.88 2.06 2.922(5) 166.8 3 N201 H201 O111 0.88 2.06 2.928(4) 169 4 O11 H11 O121 0.84 1.74 2.532(5) 155.7 . O21 H21 O221 0.84 1.81 2.580(5) 152.4 .