# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _audit_creation_date 2005-07-05 _publ_contact_letter ; This crystallographic data is for a paper submitted to Chem. Commun. by A. Ghasparian, K. Moehle, A. Linden and J.A. Robinson. ; # PROCESSING SUMMARY _journal_coden_Cambridge 182 _journal_name_full 'Chem. Commun.' _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? # SUBMISSION DETAILS _publ_contact_author_name 'John Robinson' _publ_contact_author_address ; Institute of Organic Chemistry University of Z\"urich Winterthurerstrasse 190 CH-8057 Z\"urich Switzerland ; _publ_contact_author_email ROBINSON@OCI.UNIZH.CH _publ_requested_journal 'Chem. Commun.' _publ_requested_category ? _publ_requested_coeditor_name ? # TITLE AND AUTHOR LIST _publ_section_title ; Crystal Structure of an NPNA-Repeat Motif from the Circumsporozoite Protein of the Malaria Parasite Plasmodium falciparum ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Ghasparian, Arin' . ; Institute of Organic Chemistry University of Z\"urich Winterthurerstrasse 190 CH-8057 Z\"urich Switzerland ; 'M\"ohle, Kerstin' . ; Institute of Organic Chemistry University of Z\"urich Winterthurerstrasse 190 CH-8057 Z\"urich Switzerland ; 'Linden, Anthony' . ; Institute of Organic Chemistry University of Z\"urich Winterthurerstrasse 190 CH-8057 Z\"urich Switzerland ; 'Robinson, John, A.' . ; Institute of Organic Chemistry University of Z\"urich Winterthurerstrasse 190 CH-8057 Z\"urich Switzerland ; # TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; The asymmetric unit contains one peptide and three water molecules. The space group permits the compound in the crystal to be enantiomerically pure, but the absolute configuration of the molecule has not been determined. The enantiomer used in the refinement was based on the expected S-configuration of all peptide units in the molecule. Friedel pairs were merged. ; _publ_section_acknowledgements ; ? ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Flack, H. D. & Bernardinelli, G. (1999). Acta Cryst. A55, 908--915. Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143--1148. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Sheldrick, G. M. (1997). SHELXL97. University of G\"ottingen, Germany. Spek, A. L. (2004). PLATON. University of Utrecht, The Netherlands. ; _publ_section_table_legends ; ? ; _publ_section_figure_captions ; ? ; #========================================================================== data_RO0402 _database_code_depnum_ccdc_archive 'CCDC 280279' _audit_creation_method SHELXL-97 _audit_creation_date 04-12-17 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_moiety 'C21 H34 N8 O8, 3(H2 O)' _chemical_formula_sum 'C21 H40 N8 O11' _chemical_formula_weight 580.59 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 21 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 40 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 8 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 11 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1 ' _symmetry_space_group_name_Hall ? _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.6005(3) _cell_length_b 9.0722(4) _cell_length_c 10.5034(5) _cell_angle_alpha 86.798(3) _cell_angle_beta 79.255(3) _cell_angle_gamma 79.767(3) _cell_volume 700.03(5) _cell_formula_units_Z 1 _cell_measurement_temperature 160(1) _cell_measurement_reflns_used 2373 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Solvent used: D2O Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (deg.): 0.527(3) Frames collected: 208 Seconds exposure per frame: 10 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0 ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_detector '65 mm CCD camera on \k goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 9712 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 24.94 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.989 _reflns_number_total 2415 _reflns_number_gt 2257 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2004)' _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 'w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.0568P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom & difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack & Bernardinelli (1999; 2000)' _refine_ls_abs_structure_Flack ? _chemical_absolute_configuration syn _refine_ls_number_reflns 2414 _refine_ls_number_parameters 412 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.267 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.064 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 O3 O 1.0253(3) -0.1612(3) 1.0200(2) 0.0268(5) Uani 1 1 d . . . O6 O 0.7981(3) -0.1081(3) 0.7132(2) 0.0290(5) Uani 1 1 d . . . O9 O 0.3275(3) 0.1927(3) 0.7515(3) 0.0354(6) Uani 1 1 d . . . O12 O 0.6520(4) 0.2466(3) 0.3096(2) 0.0323(6) Uani 1 1 d . . . O15 O 0.4568(3) -0.0863(3) 0.3346(3) 0.0361(6) Uani 1 1 d . . . O17 O 1.4173(4) -0.3051(3) 1.0597(3) 0.0369(6) Uani 1 1 d . . . O21 O 0.9864(3) 0.2141(3) 0.6253(2) 0.0277(5) Uani 1 1 d . . . O27 O 0.3815(3) 0.5834(3) 0.6395(2) 0.0323(6) Uani 1 1 d . . . N1 N 1.1987(4) -0.4460(3) 1.0867(3) 0.0276(6) Uani 1 1 d . . . H1 H 1.1342 -0.5041 1.1385 0.033 Uiso 1 1 calc R . . N4 N 1.1420(4) -0.2021(3) 0.8091(3) 0.0243(6) Uani 1 1 d . . . H4 H 1.2081 -0.2659 0.7517 0.029 Uiso 1 1 calc R . . N7 N 0.7621(3) 0.0744(3) 0.8579(3) 0.0216(6) Uani 1 1 d . . . N10 N 0.6142(4) 0.2213(3) 0.6582(3) 0.0220(6) Uani 1 1 d . . . H10 H 0.7282 0.2071 0.6689 0.026 Uiso 1 1 calc R . . N13 N 0.6981(4) 0.0447(3) 0.4419(3) 0.0261(6) Uani 1 1 d . . . H13 H 0.6899 0.0089 0.5220 0.031 Uiso 1 1 calc R . . N16 N 0.6694(5) -0.1637(4) 0.1617(3) 0.0357(7) Uani 1 1 d D . . H161 H 0.787(7) -0.163(5) 0.113(5) 0.042(12) Uiso 1 1 d . . . H162 H 0.603(8) -0.206(7) 0.126(6) 0.074(18) Uiso 1 1 d D . . N22 N 1.2087(4) 0.1518(4) 0.4546(3) 0.0288(7) Uani 1 1 d . . . H221 H 1.287(6) 0.088(5) 0.413(4) 0.028(11) Uiso 1 1 d . . . H222 H 1.168(7) 0.225(7) 0.416(5) 0.042(13) Uiso 1 1 d . . . N28 N 0.6568(5) 0.6191(4) 0.6713(3) 0.0353(7) Uani 1 1 d . . . H281 H 0.601(6) 0.696(6) 0.725(5) 0.042(12) Uiso 1 1 d . . . H282 H 0.772(7) 0.600(5) 0.641(4) 0.029(10) Uiso 1 1 d . . . C2 C 1.1655(5) -0.4145(3) 0.9562(3) 0.0249(7) Uani 1 1 d . . . H2 H 1.2789 -0.4515 0.8934 0.030 Uiso 1 1 calc R . . C3 C 1.1078(4) -0.2464(4) 0.9323(3) 0.0203(7) Uani 1 1 d . . . C5 C 1.0731(4) -0.0503(3) 0.7656(3) 0.0215(7) Uani 1 1 d . . . H5 H 1.1054 0.0247 0.8197 0.026 Uiso 1 1 calc R . . C6 C 0.8661(4) -0.0299(3) 0.7781(3) 0.0222(7) Uani 1 1 d . . . C8 C 0.5628(4) 0.1001(4) 0.8730(3) 0.0250(7) Uani 1 1 d . . . H8 H 0.5174 0.0031 0.8937 0.030 Uiso 1 1 calc R . . C9 C 0.4914(4) 0.1761(4) 0.7541(3) 0.0234(7) Uani 1 1 d . . . C11 C 0.5719(4) 0.2920(4) 0.5381(3) 0.0233(7) Uani 1 1 d . . . H11 H 0.4365 0.3152 0.5472 0.028 Uiso 1 1 calc R . . C12 C 0.6451(4) 0.1924(4) 0.4204(3) 0.0231(7) Uani 1 1 d . . . C14 C 0.7686(4) -0.0558(4) 0.3348(3) 0.0252(7) Uani 1 1 d . . . H14 H 0.8443 -0.0021 0.2656 0.030 Uiso 1 1 calc R . . C15 C 0.6166(5) -0.1024(4) 0.2760(3) 0.0273(7) Uani 1 1 d . . . C17 C 1.3263(5) -0.3881(4) 1.1300(4) 0.0307(8) Uani 1 1 d . . . C18 C 1.3527(6) -0.4335(5) 1.2655(4) 0.0400(9) Uani 1 1 d . . . H181 H 1.3757 -0.3477 1.3087 0.060 Uiso 1 1 calc R . . H182 H 1.4566 -0.5153 1.2628 0.060 Uiso 1 1 calc R . . H183 H 1.2431 -0.4673 1.3136 0.060 Uiso 1 1 calc R . . C19 C 1.0144(6) -0.4945(5) 0.9340(4) 0.0417(10) Uani 1 1 d . . . H191 H 0.9029 -0.4584 0.9952 0.063 Uiso 1 1 calc R . . H192 H 1.0502 -0.6026 0.9474 0.063 Uiso 1 1 calc R . . H193 H 0.9927 -0.4739 0.8451 0.063 Uiso 1 1 calc R . . C20 C 1.1642(5) -0.0325(4) 0.6248(3) 0.0248(7) Uani 1 1 d . . . H201 H 1.2976 -0.0552 0.6194 0.030 Uiso 1 1 calc R . . H202 H 1.1300 -0.1067 0.5724 0.030 Uiso 1 1 calc R . . C21 C 1.1141(4) 0.1217(4) 0.5673(3) 0.0229(7) Uani 1 1 d . . . C23 C 0.8259(5) 0.1793(4) 0.9346(3) 0.0272(7) Uani 1 1 d . . . H231 H 0.9225 0.2273 0.8808 0.033 Uiso 1 1 calc R . . H232 H 0.8728 0.1273 1.0100 0.033 Uiso 1 1 calc R . . C24 C 0.6554(5) 0.2941(4) 0.9781(3) 0.0296(8) Uani 1 1 d . . . H241 H 0.6417 0.3764 0.9129 0.036 Uiso 1 1 calc R . . H242 H 0.6584 0.3369 1.0622 0.036 Uiso 1 1 calc R . . C25 C 0.5018(5) 0.2025(4) 0.9907(3) 0.0301(8) Uani 1 1 d . . . H251 H 0.3840 0.2680 0.9865 0.036 Uiso 1 1 calc R . . H252 H 0.4909 0.1432 1.0730 0.036 Uiso 1 1 calc R . . C26 C 0.6440(4) 0.4405(4) 0.5131(3) 0.0238(7) Uani 1 1 d . . . H261 H 0.7762 0.4221 0.5135 0.029 Uiso 1 1 calc R . . H262 H 0.6250 0.4815 0.4264 0.029 Uiso 1 1 calc R . . C27 C 0.5497(5) 0.5535(4) 0.6143(3) 0.0257(7) Uani 1 1 d . . . C29 C 0.8902(6) -0.1949(4) 0.3772(4) 0.0408(9) Uani 1 1 d . . . H291 H 0.8198 -0.2477 0.4472 0.061 Uiso 1 1 calc R . . H292 H 0.9924 -0.1653 0.4083 0.061 Uiso 1 1 calc R . . H293 H 0.9365 -0.2613 0.3035 0.061 Uiso 1 1 calc R . . O30 O 0.0270(5) 0.3103(3) 0.2278(3) 0.0389(7) Uani 1 1 d . . . H301 H -0.089(8) 0.305(6) 0.256(5) 0.048(13) Uiso 1 1 d . . . H302 H 0.071(11) 0.234(11) 0.186(8) 0.10(3) Uiso 1 1 d . . . O31 O 0.0507(4) 0.5087(3) 0.5830(3) 0.0398(7) Uani 1 1 d . . . H311 H 0.149(9) 0.535(7) 0.583(6) 0.061(16) Uiso 1 1 d . . . H312 H 0.040(9) 0.421(9) 0.596(7) 0.08(2) Uiso 1 1 d . . . O32 O 0.1843(4) 0.0159(4) 0.1686(3) 0.0453(7) Uani 1 1 d . . . H321 H 0.263(8) -0.032(6) 0.217(6) 0.054(15) Uiso 1 1 d . . . H322 H 0.161(8) -0.046(7) 0.112(6) 0.063(16) Uiso 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 O3 0.0266(12) 0.0265(12) 0.0269(12) -0.0016(10) -0.0069(10) -0.0009(10) O6 0.0326(13) 0.0225(11) 0.0340(13) -0.0052(10) -0.0101(10) -0.0041(10) O9 0.0232(13) 0.0499(16) 0.0351(14) 0.0021(11) -0.0092(10) -0.0087(11) O12 0.0423(14) 0.0277(13) 0.0250(13) -0.0008(10) -0.0100(10) 0.0034(10) O15 0.0255(13) 0.0391(15) 0.0424(15) -0.0154(12) 0.0004(11) -0.0040(11) O17 0.0350(13) 0.0363(14) 0.0443(15) -0.0029(12) -0.0165(12) -0.0088(12) O21 0.0211(12) 0.0267(13) 0.0329(13) 0.0028(10) -0.0038(10) 0.0004(10) O27 0.0266(13) 0.0279(13) 0.0410(15) -0.0092(11) -0.0058(10) 0.0013(10) N1 0.0344(16) 0.0247(15) 0.0258(15) 0.0013(12) -0.0114(12) -0.0047(12) N4 0.0284(14) 0.0189(14) 0.0235(14) -0.0023(11) -0.0068(11) 0.0041(11) N7 0.0210(14) 0.0209(13) 0.0229(13) -0.0025(11) -0.0050(11) -0.0022(11) N10 0.0187(13) 0.0223(14) 0.0254(14) -0.0008(11) -0.0083(11) 0.0006(11) N13 0.0298(15) 0.0221(15) 0.0253(15) -0.0030(11) -0.0054(11) -0.0003(11) N16 0.0265(17) 0.048(2) 0.0341(17) -0.0167(14) -0.0035(14) -0.0067(14) N22 0.0290(16) 0.0278(18) 0.0270(16) 0.0046(15) -0.0059(14) 0.0015(14) N28 0.035(2) 0.0313(18) 0.0415(19) -0.0115(15) -0.0099(15) -0.0032(14) C2 0.0315(18) 0.0187(16) 0.0253(17) 0.0003(13) -0.0104(14) -0.0008(13) C3 0.0188(16) 0.0230(16) 0.0210(15) 0.0009(13) -0.0083(13) -0.0040(13) C5 0.0232(16) 0.0174(15) 0.0233(16) 0.0005(12) -0.0065(13) 0.0006(12) C6 0.0277(17) 0.0171(15) 0.0211(16) 0.0017(12) -0.0041(13) -0.0029(13) C8 0.0220(16) 0.0244(17) 0.0274(17) 0.0005(13) -0.0020(13) -0.0037(13) C9 0.0221(18) 0.0213(16) 0.0275(17) -0.0044(13) -0.0063(13) -0.0029(13) C11 0.0210(15) 0.0269(18) 0.0224(16) -0.0008(13) -0.0077(12) -0.0013(13) C12 0.0184(15) 0.0228(17) 0.0287(18) 0.0005(14) -0.0097(13) 0.0000(13) C14 0.0290(18) 0.0210(17) 0.0255(17) -0.0043(13) -0.0064(14) -0.0015(14) C15 0.0273(18) 0.0225(17) 0.0316(18) -0.0046(14) -0.0044(14) -0.0031(13) C17 0.0289(18) 0.0242(17) 0.040(2) -0.0042(15) -0.0155(15) 0.0052(14) C18 0.048(2) 0.038(2) 0.036(2) -0.0025(17) -0.0249(18) 0.0057(18) C19 0.057(3) 0.035(2) 0.043(2) 0.0073(17) -0.0273(19) -0.0193(19) C20 0.0262(16) 0.0201(16) 0.0261(17) -0.0011(13) -0.0044(13) 0.0008(13) C21 0.0207(16) 0.0232(16) 0.0260(17) 0.0004(13) -0.0084(13) -0.0027(13) C23 0.0310(18) 0.0252(17) 0.0268(18) -0.0057(14) -0.0084(14) -0.0033(14) C24 0.0318(18) 0.0275(18) 0.0280(17) -0.0055(14) -0.0069(14) 0.0021(14) C25 0.0285(18) 0.037(2) 0.0214(17) -0.0035(14) -0.0032(14) 0.0028(15) C26 0.0214(16) 0.0248(17) 0.0257(16) 0.0003(13) -0.0084(13) -0.0016(13) C27 0.0301(18) 0.0203(16) 0.0280(17) 0.0030(13) -0.0090(14) -0.0050(13) C29 0.049(2) 0.031(2) 0.040(2) -0.0072(17) -0.0190(18) 0.0134(17) O30 0.0421(18) 0.0334(15) 0.0411(16) 0.0034(13) -0.0070(13) -0.0080(13) O31 0.0373(17) 0.0278(15) 0.0580(18) 0.0031(13) -0.0187(14) -0.0063(13) O32 0.0395(16) 0.0406(16) 0.0590(19) -0.0159(14) -0.0176(15) -0.0018(13) _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 O3 C3 1.238(4) . ? O6 C6 1.245(4) . ? O9 C9 1.233(4) . ? O12 C12 1.233(4) . ? O15 C15 1.243(4) . ? O17 C17 1.235(5) . ? O21 C21 1.251(4) . ? O27 C27 1.239(4) . ? N1 C17 1.340(5) . ? N1 C2 1.444(4) . ? N1 H1 0.8800 . ? N4 C3 1.326(4) . ? N4 C5 1.464(4) . ? N4 H4 0.8800 . ? N7 C6 1.341(4) . ? N7 C8 1.471(4) . ? N7 C23 1.478(4) . ? N10 C9 1.339(4) . ? N10 C11 1.447(4) . ? N10 H10 0.8800 . ? N13 C12 1.348(4) . ? N13 C14 1.449(4) . ? N13 H13 0.8800 . ? N16 C15 1.314(5) . ? N16 H161 0.94(5) . ? N16 H162 0.83(4) . ? N22 C21 1.307(5) . ? N22 H221 0.83(5) . ? N22 H222 0.80(6) . ? N28 C27 1.330(5) . ? N28 H281 0.91(5) . ? N28 H282 0.86(5) . ? C2 C19 1.522(5) . ? C2 C3 1.530(4) . ? C2 H2 1.0000 . ? C5 C20 1.524(4) . ? C5 C6 1.533(4) . ? C5 H5 1.0000 . ? C8 C9 1.534(5) . ? C8 C25 1.539(5) . ? C8 H8 1.0000 . ? C11 C12 1.532(4) . ? C11 C26 1.534(5) . ? C11 H11 1.0000 . ? C14 C29 1.524(5) . ? C14 C15 1.537(5) . ? C14 H14 1.0000 . ? C17 C18 1.498(5) . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 H191 0.9800 . ? C19 H192 0.9800 . ? C19 H193 0.9800 . ? C20 C21 1.506(5) . ? C20 H201 0.9900 . ? C20 H202 0.9900 . ? C23 C24 1.525(5) . ? C23 H231 0.9900 . ? C23 H232 0.9900 . ? C24 C25 1.531(5) . ? C24 H241 0.9900 . ? C24 H242 0.9900 . ? C25 H251 0.9900 . ? C25 H252 0.9900 . ? C26 C27 1.508(5) . ? C26 H261 0.9900 . ? C26 H262 0.9900 . ? C29 H291 0.9800 . ? C29 H292 0.9800 . ? C29 H293 0.9800 . ? O30 H301 0.88(6) . ? O30 H302 0.82(10) . ? O31 H311 0.82(7) . ? O31 H312 0.81(8) . ? O32 H321 0.89(7) . ? O32 H322 0.90(7) . ? 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 C17 N1 C2 120.9(3) . . ? C17 N1 H1 119.5 . . ? C2 N1 H1 119.5 . . ? C3 N4 C5 122.0(3) . . ? C3 N4 H4 119.0 . . ? C5 N4 H4 119.0 . . ? C6 N7 C8 121.2(3) . . ? C6 N7 C23 126.7(3) . . ? C8 N7 C23 112.0(3) . . ? C9 N10 C11 124.3(3) . . ? C9 N10 H10 117.9 . . ? C11 N10 H10 117.9 . . ? C12 N13 C14 120.8(3) . . ? C12 N13 H13 119.6 . . ? C14 N13 H13 119.6 . . ? C15 N16 H161 122(3) . . ? C15 N16 H162 123(4) . . ? H161 N16 H162 115(5) . . ? C21 N22 H221 123(3) . . ? C21 N22 H222 117(3) . . ? H221 N22 H222 118(5) . . ? C27 N28 H281 117(3) . . ? C27 N28 H282 117(3) . . ? H281 N28 H282 124(4) . . ? N1 C2 C19 109.5(3) . . ? N1 C2 C3 111.3(3) . . ? C19 C2 C3 108.4(3) . . ? N1 C2 H2 109.2 . . ? C19 C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? O3 C3 N4 122.9(3) . . ? O3 C3 C2 122.4(3) . . ? N4 C3 C2 114.5(3) . . ? N4 C5 C20 107.1(2) . . ? N4 C5 C6 109.3(2) . . ? C20 C5 C6 111.0(3) . . ? N4 C5 H5 109.8 . . ? C20 C5 H5 109.8 . . ? C6 C5 H5 109.8 . . ? O6 C6 N7 121.5(3) . . ? O6 C6 C5 119.8(3) . . ? N7 C6 C5 118.7(3) . . ? N7 C8 C9 113.6(3) . . ? N7 C8 C25 102.9(3) . . ? C9 C8 C25 110.7(3) . . ? N7 C8 H8 109.8 . . ? C9 C8 H8 109.8 . . ? C25 C8 H8 109.8 . . ? O9 C9 N10 123.8(3) . . ? O9 C9 C8 119.4(3) . . ? N10 C9 C8 116.8(3) . . ? N10 C11 C12 113.4(3) . . ? N10 C11 C26 110.8(3) . . ? C12 C11 C26 109.3(3) . . ? N10 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? C26 C11 H11 107.7 . . ? O12 C12 N13 121.6(3) . . ? O12 C12 C11 120.4(3) . . ? N13 C12 C11 118.0(3) . . ? N13 C14 C29 110.7(3) . . ? N13 C14 C15 112.3(3) . . ? C29 C14 C15 109.7(3) . . ? N13 C14 H14 108.0 . . ? C29 C14 H14 108.0 . . ? C15 C14 H14 108.0 . . ? O15 C15 N16 122.9(3) . . ? O15 C15 C14 121.9(3) . . ? N16 C15 C14 115.1(3) . . ? O17 C17 N1 120.8(3) . . ? O17 C17 C18 123.2(3) . . ? N1 C17 C18 116.0(3) . . ? C17 C18 H181 109.5 . . ? C17 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C17 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C2 C19 H191 109.5 . . ? C2 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C2 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? C21 C20 C5 113.7(3) . . ? C21 C20 H201 108.8 . . ? C5 C20 H201 108.8 . . ? C21 C20 H202 108.8 . . ? C5 C20 H202 108.8 . . ? H201 C20 H202 107.7 . . ? O21 C21 N22 122.6(3) . . ? O21 C21 C20 120.7(3) . . ? N22 C21 C20 116.7(3) . . ? N7 C23 C24 103.4(3) . . ? N7 C23 H231 111.1 . . ? C24 C23 H231 111.1 . . ? N7 C23 H232 111.1 . . ? C24 C23 H232 111.1 . . ? H231 C23 H232 109.1 . . ? C23 C24 C25 103.3(3) . . ? C23 C24 H241 111.1 . . ? C25 C24 H241 111.1 . . ? C23 C24 H242 111.1 . . ? C25 C24 H242 111.1 . . ? H241 C24 H242 109.1 . . ? C24 C25 C8 102.8(3) . . ? C24 C25 H251 111.2 . . ? C8 C25 H251 111.2 . . ? C24 C25 H252 111.2 . . ? C8 C25 H252 111.2 . . ? H251 C25 H252 109.1 . . ? C27 C26 C11 111.4(3) . . ? C27 C26 H261 109.3 . . ? C11 C26 H261 109.3 . . ? C27 C26 H262 109.3 . . ? C11 C26 H262 109.3 . . ? H261 C26 H262 108.0 . . ? O27 C27 N28 123.2(3) . . ? O27 C27 C26 120.6(3) . . ? N28 C27 C26 116.2(3) . . ? C14 C29 H291 109.5 . . ? C14 C29 H292 109.5 . . ? H291 C29 H292 109.5 . . ? C14 C29 H293 109.5 . . ? H291 C29 H293 109.5 . . ? H292 C29 H293 109.5 . . ? H301 O30 H302 106(7) . . ? H311 O31 H312 120(7) . . ? H321 O32 H322 112(5) . . ? 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 C17 N1 C2 C19 180.0(3) . . . . ? C17 N1 C2 C3 -60.2(4) . . . . ? C5 N4 C3 O3 -4.4(5) . . . . ? C5 N4 C3 C2 171.0(3) . . . . ? N1 C2 C3 O3 -29.3(4) . . . . ? C19 C2 C3 O3 91.2(4) . . . . ? N1 C2 C3 N4 155.2(3) . . . . ? C19 C2 C3 N4 -84.3(3) . . . . ? C3 N4 C5 C20 170.8(3) . . . . ? C3 N4 C5 C6 -68.7(4) . . . . ? C8 N7 C6 O6 0.4(5) . . . . ? C23 N7 C6 O6 -176.6(3) . . . . ? C8 N7 C6 C5 179.4(3) . . . . ? C23 N7 C6 C5 2.4(5) . . . . ? N4 C5 C6 O6 -62.9(4) . . . . ? C20 C5 C6 O6 55.1(4) . . . . ? N4 C5 C6 N7 118.1(3) . . . . ? C20 C5 C6 N7 -123.9(3) . . . . ? C6 N7 C8 C9 -71.3(4) . . . . ? C23 N7 C8 C9 106.1(3) . . . . ? C6 N7 C8 C25 169.0(3) . . . . ? C23 N7 C8 C25 -13.6(3) . . . . ? C11 N10 C9 O9 -1.6(5) . . . . ? C11 N10 C9 C8 178.7(3) . . . . ? N7 C8 C9 O9 174.4(3) . . . . ? C25 C8 C9 O9 -70.4(4) . . . . ? N7 C8 C9 N10 -5.9(4) . . . . ? C25 C8 C9 N10 109.4(3) . . . . ? C9 N10 C11 C12 -109.9(3) . . . . ? C9 N10 C11 C26 126.9(3) . . . . ? C14 N13 C12 O12 1.1(5) . . . . ? C14 N13 C12 C11 180.0(3) . . . . ? N10 C11 C12 O12 -165.4(3) . . . . ? C26 C11 C12 O12 -41.3(4) . . . . ? N10 C11 C12 N13 15.7(4) . . . . ? C26 C11 C12 N13 139.8(3) . . . . ? C12 N13 C14 C29 155.8(3) . . . . ? C12 N13 C14 C15 -81.2(4) . . . . ? N13 C14 C15 O15 -17.0(5) . . . . ? C29 C14 C15 O15 106.6(4) . . . . ? N13 C14 C15 N16 164.8(3) . . . . ? C29 C14 C15 N16 -71.6(4) . . . . ? C2 N1 C17 O17 0.8(5) . . . . ? C2 N1 C17 C18 -177.8(3) . . . . ? N4 C5 C20 C21 -177.1(3) . . . . ? C6 C5 C20 C21 63.5(3) . . . . ? C5 C20 C21 O21 -11.4(4) . . . . ? C5 C20 C21 N22 169.4(3) . . . . ? C6 N7 C23 C24 166.2(3) . . . . ? C8 N7 C23 C24 -11.0(4) . . . . ? N7 C23 C24 C25 31.2(3) . . . . ? C23 C24 C25 C8 -39.8(3) . . . . ? N7 C8 C25 C24 32.6(3) . . . . ? C9 C8 C25 C24 -89.2(3) . . . . ? N10 C11 C26 C27 -64.9(3) . . . . ? C12 C11 C26 C27 169.5(3) . . . . ? C11 C26 C27 O27 -52.2(4) . . . . ? C11 C26 C27 N28 129.0(3) . . . . ? 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 _geom_hbond_publ_flag N1 H1 O30 0.88 2.10 2.954(4) 163.7 1_646 yes N4 H4 O27 0.88 1.99 2.863(4) 172.0 1_645 yes N10 H10 O21 0.88 1.94 2.774(3) 157.2 . yes N13 H13 O6 0.88 2.43 3.257(4) 156.9 . yes N16 H161 O3 0.94(5) 1.89(5) 2.837(4) 178(4) 1_554 yes N16 H162 O17 0.83(4) 2.05(4) 2.873(4) 173(6) 1_454 yes N22 H221 O15 0.83(5) 1.97(5) 2.790(4) 171(4) 1_655 yes N22 H222 O30 0.80(6) 2.44(6) 3.128(5) 144(5) 1_655 yes N28 H281 O6 0.91(5) 2.50(5) 2.952(4) 111(3) 1_565 yes N28 H282 O31 0.86(5) 2.12(5) 2.971(5) 168(4) 1_655 yes O30 H301 O12 0.88(6) 2.10(6) 2.969(4) 168(5) 1_455 yes O30 H302 O32 0.82(10) 2.02(10) 2.779(5) 154(8) . yes O31 H311 O27 0.82(7) 2.09(7) 2.888(4) 163(6) . yes O31 H312 O21 0.81(8) 1.99(8) 2.798(4) 174(7) 1_455 yes O32 H321 O15 0.89(7) 2.07(7) 2.945(4) 165(5) . yes O32 H322 O3 0.90(7) 1.99(7) 2.855(4) 161(5) 1_454 yes # End of CIF ============================================================