# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Nauha, Elisa' 'Kolehmainen, Erkki' 'Nissinen, Maija' _publ_contact_author_name 'Nissinen, Maija' _publ_contact_author_email maija.nissinen@jyu.fi _publ_section_title ; Packing incentives and a reliable N-H***N-pyridine synthon in co-crystallization of bipyridines with two agrochemical actives ; # Attachment '- bp_bpe_co-crystals.cif' data_TM-22bp _database_code_depnum_ccdc_archive 'CCDC 831123' #TrackingRef '- bp_bpe_co-crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H14 N4 O4 S2), 1.5(C10 H8 N2), C2 H3 N' _chemical_formula_sum 'C41 H43 N12 O8 S4' _chemical_formula_weight 960.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6193(3) _cell_length_b 15.0562(4) _cell_length_c 16.2601(4) _cell_angle_alpha 108.694(4) _cell_angle_beta 95.323(3) _cell_angle_gamma 109.312(4) _cell_volume 2265.87(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1002 _exptl_absorpt_coefficient_mu 2.480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7073 _exptl_absorpt_correction_T_max 0.7895 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10805 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 66.97 _reflns_number_total 7733 _reflns_number_gt 5900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0609P)^2^+2.0584P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7733 _refine_ls_number_parameters 615 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.52467(10) 0.79919(6) 0.36781(5) 0.0537(3) Uani 1 1 d . . . S2 S 0.78623(7) 0.92107(6) 0.10033(5) 0.0393(2) Uani 1 1 d . . . S3 S 0.48577(13) 0.64022(7) 0.50102(5) 0.0651(3) Uani 1 1 d . . . S4 S 0.90597(8) 0.78347(6) 0.83007(6) 0.0444(2) Uani 1 1 d . . . O1 O 0.6729(2) 1.10580(16) 0.33620(13) 0.0463(6) Uani 1 1 d . . . O2 O 0.7640(2) 1.15755(17) 0.48222(13) 0.0482(6) Uani 1 1 d . . . O3 O 0.58950(19) 1.15657(15) 0.17227(13) 0.0337(4) Uani 1 1 d . . . O4 O 0.8118(2) 1.26190(15) 0.20624(15) 0.0424(5) Uani 1 1 d . . . O5 O 0.6971(2) 0.95216(16) 0.72444(13) 0.0464(6) Uani 1 1 d . . . O6 O 0.6977(2) 1.00098(15) 0.60756(13) 0.0412(5) Uani 1 1 d . . . O7 O 0.71268(19) 1.01966(15) 0.92307(12) 0.0345(4) Uani 1 1 d . . . O8 O 0.9272(2) 1.12299(15) 0.92932(14) 0.0414(5) Uani 1 1 d . . . N1 N 0.6355(3) 0.9955(2) 0.40995(16) 0.0403(6) Uani 1 1 d D . . H1N H 0.663(3) 0.993(3) 0.4627(15) 0.048 Uiso 1 1 d D . . N2 N 0.5313(3) 0.90622(19) 0.26198(15) 0.0368(6) Uani 1 1 d D . . H2N H 0.570(3) 0.9661(17) 0.259(2) 0.044 Uiso 1 1 d D . . N3 N 0.5625(2) 0.96020(18) 0.11891(15) 0.0291(5) Uani 1 1 d D . . H3N H 0.518(3) 1.002(2) 0.124(2) 0.035 Uiso 1 1 d D . . N4 N 0.7630(2) 1.09835(18) 0.14544(15) 0.0311(5) Uani 1 1 d D . . H4N H 0.8533(19) 1.124(2) 0.152(2) 0.037 Uiso 1 1 d D . . N5 N 0.5927(3) 0.83702(19) 0.58182(16) 0.0388(6) Uani 1 1 d D . . H5N H 0.575(3) 0.830(3) 0.5245(14) 0.047 Uiso 1 1 d D . . N6 N 0.5759(3) 0.75134(19) 0.67708(15) 0.0350(6) Uani 1 1 d D . . H6N H 0.618(3) 0.8146(16) 0.7155(18) 0.042 Uiso 1 1 d D . . N7 N 0.6831(2) 0.82179(17) 0.85312(14) 0.0282(5) Uani 1 1 d D . . H7N H 0.641(3) 0.864(2) 0.8728(18) 0.034 Uiso 1 1 d D . . N8 N 0.8864(2) 0.96158(18) 0.89616(15) 0.0320(5) Uani 1 1 d D . . H8N H 0.9780(19) 0.988(2) 0.897(2) 0.038 Uiso 1 1 d D . . C1 C 0.8272(4) 1.2603(3) 0.4852(2) 0.0563(9) Uani 1 1 d . . . H1A H 0.8787 1.2603 0.4383 0.084 Uiso 1 1 calc R . . H1B H 0.8894 1.3036 0.5434 0.084 Uiso 1 1 calc R . . H1C H 0.7560 1.2864 0.4760 0.084 Uiso 1 1 calc R . . C2 C 0.6901(3) 1.0886(2) 0.4031(2) 0.0387(7) Uani 1 1 d . . . C3 C 0.5627(3) 0.9013(2) 0.34205(19) 0.0384(7) Uani 1 1 d . . . C4 C 0.4669(3) 0.8282(2) 0.17751(17) 0.0313(6) Uani 1 1 d . . . C5 C 0.3848(3) 0.7286(2) 0.16299(19) 0.0368(7) Uani 1 1 d . . . H5 H 0.3667 0.7090 0.2121 0.044 Uiso 1 1 calc R . . C6 C 0.3293(3) 0.6580(2) 0.07654(19) 0.0360(7) Uani 1 1 d . . . H6 H 0.2734 0.5900 0.0669 0.043 Uiso 1 1 calc R . . C7 C 0.3541(3) 0.6851(2) 0.00481(18) 0.0339(6) Uani 1 1 d . . . H7 H 0.3181 0.6355 -0.0540 0.041 Uiso 1 1 calc R . . C8 C 0.4316(3) 0.7849(2) 0.01831(18) 0.0313(6) Uani 1 1 d . . . H8 H 0.4470 0.8042 -0.0312 0.038 Uiso 1 1 calc R . . C9 C 0.4864(3) 0.8562(2) 0.10381(17) 0.0281(6) Uani 1 1 d . . . C10 C 0.6970(3) 0.9955(2) 0.12198(17) 0.0286(6) Uani 1 1 d . . . C11 C 0.7094(3) 1.1715(2) 0.17518(18) 0.0308(6) Uani 1 1 d . . . C12 C 0.7762(3) 1.3487(2) 0.2470(2) 0.0488(8) Uani 1 1 d . . . H12A H 0.7034 1.3482 0.2050 0.073 Uiso 1 1 calc R . . H12B H 0.8570 1.4113 0.2627 0.073 Uiso 1 1 calc R . . H12C H 0.7443 1.3450 0.3009 0.073 Uiso 1 1 calc R . . C13 C 0.7838(4) 1.1040(2) 0.6676(2) 0.0482(8) Uani 1 1 d . . . H13A H 0.8711 1.1051 0.6945 0.072 Uiso 1 1 calc R . . H13B H 0.7374 1.1273 0.7145 0.072 Uiso 1 1 calc R . . H13C H 0.8009 1.1490 0.6341 0.072 Uiso 1 1 calc R . . C14 C 0.6658(3) 0.9320(2) 0.64538(19) 0.0373(7) Uani 1 1 d . . . C15 C 0.5527(3) 0.7444(2) 0.59259(19) 0.0391(7) Uani 1 1 d . . . C16 C 0.5495(3) 0.6780(2) 0.71616(18) 0.0308(6) Uani 1 1 d . . . C17 C 0.4749(3) 0.5743(2) 0.6726(2) 0.0387(7) Uani 1 1 d . . . H17 H 0.4408 0.5466 0.6100 0.046 Uiso 1 1 calc R . . C18 C 0.4503(3) 0.5113(2) 0.7205(2) 0.0425(7) Uani 1 1 d . . . H18 H 0.3992 0.4406 0.6903 0.051 Uiso 1 1 calc R . . C19 C 0.4989(3) 0.5499(2) 0.8113(2) 0.0400(7) Uani 1 1 d . . . H19 H 0.4796 0.5064 0.8437 0.048 Uiso 1 1 calc R . . C20 C 0.5762(3) 0.6527(2) 0.8553(2) 0.0351(6) Uani 1 1 d . . . H20 H 0.6117 0.6795 0.9178 0.042 Uiso 1 1 calc R . . C21 C 0.6015(3) 0.7156(2) 0.80833(18) 0.0291(6) Uani 1 1 d . . . C22 C 0.8184(3) 0.8580(2) 0.86138(18) 0.0304(6) Uani 1 1 d . . . C23 C 0.8302(3) 1.0342(2) 0.91709(18) 0.0311(6) Uani 1 1 d . . . C24 C 0.8879(3) 1.2091(2) 0.9539(2) 0.0468(8) Uani 1 1 d . . . H24A H 0.8675 1.2221 1.0132 0.070 Uiso 1 1 calc R . . H24B H 0.8065 1.1950 0.9105 0.070 Uiso 1 1 calc R . . H24C H 0.9631 1.2688 0.9548 0.070 Uiso 1 1 calc R . . N101 N 1.0876(3) 0.6251(2) 0.26998(18) 0.0514(7) Uani 1 1 d . . . N102 N 0.8292(3) 0.5747(2) 0.08377(17) 0.0453(6) Uani 1 1 d . . . C101 C 1.1819(4) 0.5894(3) 0.2889(2) 0.0618(10) Uani 1 1 d . . . H101 H 1.2422 0.6241 0.3460 0.074 Uiso 1 1 calc R . . C102 C 1.1976(4) 0.5064(3) 0.2318(2) 0.0564(9) Uani 1 1 d . . . H102 H 1.2655 0.4839 0.2494 0.068 Uiso 1 1 calc R . . C103 C 1.1133(3) 0.4568(3) 0.1489(2) 0.0478(8) Uani 1 1 d . . . H103 H 1.1215 0.3990 0.1077 0.057 Uiso 1 1 calc R . . C104 C 1.0158(3) 0.4921(2) 0.1260(2) 0.0393(7) Uani 1 1 d . . . H104 H 0.9574 0.4598 0.0683 0.047 Uiso 1 1 calc R . . C105 C 1.0046(3) 0.5757(2) 0.1886(2) 0.0375(7) Uani 1 1 d . . . C106 C 0.8987(3) 0.6142(2) 0.1685(2) 0.0374(7) Uani 1 1 d . . . C107 C 0.8721(4) 0.6870(3) 0.2335(2) 0.0571(9) Uani 1 1 d . . . H107 H 0.9216 0.7136 0.2935 0.068 Uiso 1 1 calc R . . C108 C 0.7728(4) 0.7205(3) 0.2102(3) 0.0677(11) Uani 1 1 d . . . H108 H 0.7540 0.7709 0.2540 0.081 Uiso 1 1 calc R . . C109 C 0.7020(4) 0.6806(3) 0.1238(3) 0.0539(9) Uani 1 1 d . . . H109 H 0.6334 0.7024 0.1061 0.065 Uiso 1 1 calc R . . C110 C 0.7330(4) 0.6083(3) 0.0637(2) 0.0517(9) Uani 1 1 d . . . H110 H 0.6831 0.5801 0.0037 0.062 Uiso 1 1 calc R . . N200 N 0.9571(5) 0.9939(6) 0.3872(3) 0.137(3) Uani 1 1 d . . . C201 C 0.9931(10) 1.0637(11) 0.3440(5) 0.167(6) Uani 1 1 d . . . H201 H 0.9560 1.0408 0.2821 0.200 Uiso 1 1 calc R . . C202 C 1.0767(11) 1.1596(11) 0.3867(9) 0.166(5) Uani 1 1 d . . . H202 H 1.0983 1.2035 0.3547 0.199 Uiso 1 1 calc R . . C203 C 1.1332(8) 1.1973(9) 0.4770(8) 0.163(4) Uani 1 1 d . . . H203 H 1.1929 1.2663 0.5072 0.196 Uiso 1 1 calc R . . C204 C 1.1013(6) 1.1339(7) 0.5203(4) 0.110(2) Uani 1 1 d . . . H204 H 1.1381 1.1581 0.5825 0.132 Uiso 1 1 calc R . . C205 C 1.0161(5) 1.0345(6) 0.4761(3) 0.100(2) Uani 1 1 d . . . N300 N 0.8853(10) 0.5410(7) 0.4366(6) 0.287(7) Uani 1 1 d . . . C301 C 0.8704(9) 0.5508(6) 0.5090(5) 0.173(4) Uani 1 1 d . . . C302 C 0.8389(9) 0.5740(6) 0.5904(5) 0.159(4) Uani 1 1 d . . . H30A H 0.7423 0.5652 0.5835 0.239 Uiso 1 1 calc R . . H30B H 0.8964 0.6447 0.6278 0.239 Uiso 1 1 calc R . . H30C H 0.8551 0.5290 0.6185 0.239 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 S1 0.0774(6) 0.0408(5) 0.0337(4) 0.0157(4) -0.0030(4) 0.0138(4) S2 0.0305(4) 0.0328(4) 0.0565(5) 0.0138(3) 0.0108(3) 0.0167(3) S3 0.1107(9) 0.0369(5) 0.0326(4) 0.0058(4) 0.0003(5) 0.0210(5) S4 0.0300(4) 0.0331(4) 0.0697(5) 0.0132(4) 0.0131(3) 0.0169(3) O1 0.0600(14) 0.0379(12) 0.0320(12) 0.0108(10) 0.0034(10) 0.0118(11) O2 0.0576(14) 0.0378(12) 0.0327(11) 0.0031(9) -0.0004(10) 0.0105(11) O3 0.0270(10) 0.0353(11) 0.0437(11) 0.0166(9) 0.0092(8) 0.0159(9) O4 0.0319(11) 0.0275(11) 0.0646(14) 0.0106(10) 0.0141(10) 0.0130(9) O5 0.0634(15) 0.0378(12) 0.0284(12) 0.0107(9) 0.0027(10) 0.0112(11) O6 0.0560(13) 0.0325(11) 0.0313(10) 0.0121(9) 0.0045(9) 0.0136(10) O7 0.0312(11) 0.0357(11) 0.0384(11) 0.0117(9) 0.0099(8) 0.0165(9) O8 0.0298(11) 0.0289(11) 0.0590(13) 0.0076(10) 0.0095(9) 0.0119(9) N1 0.0508(16) 0.0389(15) 0.0243(12) 0.0089(11) 0.0019(11) 0.0133(12) N2 0.0450(15) 0.0341(14) 0.0263(12) 0.0108(11) 0.0056(10) 0.0103(12) N3 0.0265(12) 0.0299(13) 0.0331(12) 0.0122(10) 0.0073(9) 0.0128(10) N4 0.0240(12) 0.0311(13) 0.0401(13) 0.0141(11) 0.0084(10) 0.0120(10) N5 0.0520(16) 0.0365(14) 0.0262(12) 0.0108(11) 0.0038(11) 0.0170(12) N6 0.0441(15) 0.0314(13) 0.0261(13) 0.0085(10) 0.0057(10) 0.0128(11) N7 0.0278(12) 0.0295(13) 0.0295(12) 0.0095(10) 0.0079(9) 0.0145(10) N8 0.0238(12) 0.0308(13) 0.0392(13) 0.0092(11) 0.0057(10) 0.0119(10) C1 0.062(2) 0.0382(19) 0.046(2) 0.0021(16) 0.0009(17) 0.0081(17) C2 0.0369(16) 0.0390(18) 0.0352(17) 0.0074(14) 0.0072(13) 0.0146(14) C3 0.0404(17) 0.0436(18) 0.0300(15) 0.0117(13) 0.0055(12) 0.0172(14) C4 0.0339(15) 0.0335(15) 0.0263(14) 0.0098(12) 0.0067(11) 0.0141(13) C5 0.0415(17) 0.0359(16) 0.0323(15) 0.0154(13) 0.0091(12) 0.0113(14) C6 0.0361(16) 0.0286(15) 0.0386(16) 0.0105(13) 0.0055(12) 0.0096(13) C7 0.0338(15) 0.0338(16) 0.0296(15) 0.0060(12) 0.0060(12) 0.0134(13) C8 0.0315(15) 0.0376(16) 0.0276(14) 0.0120(12) 0.0087(11) 0.0161(13) C9 0.0248(13) 0.0306(15) 0.0321(15) 0.0130(12) 0.0084(11) 0.0127(12) C10 0.0307(14) 0.0307(15) 0.0268(14) 0.0119(12) 0.0071(11) 0.0133(12) C11 0.0330(16) 0.0319(15) 0.0326(15) 0.0156(12) 0.0105(12) 0.0144(13) C12 0.0435(19) 0.0303(17) 0.069(2) 0.0111(16) 0.0141(16) 0.0163(15) C13 0.060(2) 0.0365(18) 0.0383(17) 0.0100(14) 0.0063(15) 0.0109(16) C14 0.0422(17) 0.0407(18) 0.0323(17) 0.0148(14) 0.0098(13) 0.0182(14) C15 0.0450(18) 0.0405(18) 0.0347(17) 0.0142(14) 0.0085(13) 0.0199(15) C16 0.0306(14) 0.0302(15) 0.0325(15) 0.0104(12) 0.0092(11) 0.0136(12) C17 0.0383(16) 0.0352(17) 0.0367(16) 0.0085(13) 0.0066(13) 0.0121(14) C18 0.0418(17) 0.0307(16) 0.0510(19) 0.0123(14) 0.0135(14) 0.0111(14) C19 0.0408(17) 0.0373(17) 0.0500(19) 0.0223(15) 0.0171(14) 0.0171(14) C20 0.0344(15) 0.0394(17) 0.0391(16) 0.0187(14) 0.0129(12) 0.0181(13) C21 0.0246(13) 0.0296(15) 0.0329(15) 0.0082(12) 0.0078(11) 0.0133(12) C22 0.0297(14) 0.0318(15) 0.0306(14) 0.0120(12) 0.0052(11) 0.0131(12) C23 0.0299(15) 0.0318(16) 0.0306(14) 0.0084(12) 0.0052(11) 0.0141(13) C24 0.0418(18) 0.0299(16) 0.065(2) 0.0112(15) 0.0109(15) 0.0160(14) N101 0.0486(17) 0.0509(17) 0.0453(16) 0.0068(13) -0.0009(13) 0.0215(14) N102 0.0508(16) 0.0432(16) 0.0440(15) 0.0161(13) 0.0063(12) 0.0219(13) C101 0.055(2) 0.075(3) 0.049(2) 0.015(2) -0.0036(17) 0.028(2) C102 0.049(2) 0.070(3) 0.060(2) 0.026(2) 0.0109(17) 0.0335(19) C103 0.050(2) 0.046(2) 0.054(2) 0.0198(16) 0.0179(16) 0.0241(16) C104 0.0411(17) 0.0373(17) 0.0400(16) 0.0135(14) 0.0104(13) 0.0159(14) C105 0.0365(16) 0.0350(16) 0.0402(17) 0.0151(14) 0.0092(13) 0.0114(13) C106 0.0378(16) 0.0263(15) 0.0429(17) 0.0101(13) 0.0080(13) 0.0087(13) C107 0.053(2) 0.049(2) 0.053(2) -0.0011(17) 0.0002(16) 0.0232(18) C108 0.064(3) 0.053(2) 0.077(3) 0.002(2) 0.010(2) 0.035(2) C109 0.047(2) 0.043(2) 0.076(3) 0.0237(19) 0.0074(18) 0.0228(17) C110 0.055(2) 0.051(2) 0.056(2) 0.0248(17) 0.0035(16) 0.0251(18) N200 0.107(4) 0.274(8) 0.043(2) 0.020(3) 0.009(2) 0.130(5) C201 0.148(8) 0.360(17) 0.069(5) 0.076(8) 0.045(5) 0.188(10) C202 0.133(8) 0.295(16) 0.165(11) 0.119(10) 0.084(7) 0.152(10) C203 0.098(6) 0.237(12) 0.170(9) 0.053(9) 0.041(6) 0.101(7) C204 0.073(4) 0.178(7) 0.072(4) 0.011(4) 0.011(3) 0.075(5) C205 0.071(3) 0.192(7) 0.043(3) 0.013(3) 0.011(2) 0.087(4) N300 0.211(9) 0.220(9) 0.180(8) -0.081(7) 0.097(7) -0.086(7) C301 0.166(8) 0.120(6) 0.105(6) -0.014(5) 0.044(5) -0.050(5) C302 0.201(9) 0.120(6) 0.093(5) 0.037(4) 0.023(5) -0.009(6) _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 S1 C3 1.655(3) . ? S2 C10 1.670(3) . ? S3 C15 1.659(3) . ? S4 C22 1.672(3) . ? O1 C2 1.208(4) . ? O2 C2 1.329(4) . ? O2 C1 1.451(4) . ? O3 C11 1.211(3) . ? O4 C11 1.329(3) . ? O4 C12 1.451(4) . ? O5 C14 1.208(3) . ? O6 C14 1.336(4) . ? O6 C13 1.456(4) . ? O7 C23 1.213(3) . ? O8 C23 1.330(3) . ? O8 C24 1.439(4) . ? N1 C2 1.374(4) . ? N1 C3 1.393(4) . ? N1 H1N 0.897(18) . ? N2 C3 1.345(4) . ? N2 C4 1.412(4) . ? N2 H2N 0.877(18) . ? N3 C10 1.339(3) . ? N3 C9 1.430(4) . ? N3 H3N 0.890(18) . ? N4 C10 1.374(4) . ? N4 C11 1.377(4) . ? N4 H4N 0.888(18) . ? N5 C14 1.373(4) . ? N5 C15 1.391(4) . ? N5 H5N 0.897(18) . ? N6 C15 1.337(4) . ? N6 C16 1.406(4) . ? N6 H6N 0.884(18) . ? N7 C22 1.334(4) . ? N7 C21 1.434(4) . ? N7 H7N 0.890(18) . ? N8 C22 1.374(4) . ? N8 C23 1.377(4) . ? N8 H8N 0.917(18) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C4 C5 1.390(4) . ? C4 C9 1.403(4) . ? C5 C6 1.389(4) . ? C5 H5 0.9500 . ? C6 C7 1.374(4) . ? C6 H6 0.9500 . ? C7 C8 1.386(4) . ? C7 H7 0.9500 . ? C8 C9 1.380(4) . ? C8 H8 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C16 C17 1.391(4) . ? C16 C21 1.403(4) . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.376(4) . ? C18 H18 0.9500 . ? C19 C20 1.386(4) . ? C19 H19 0.9500 . ? C20 C21 1.373(4) . ? C20 H20 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N101 C101 1.338(5) . ? N101 C105 1.341(4) . ? N102 C106 1.338(4) . ? N102 C110 1.339(4) . ? C101 C102 1.369(5) . ? C101 H101 0.9500 . ? C102 C103 1.365(5) . ? C102 H102 0.9500 . ? C103 C104 1.383(4) . ? C103 H103 0.9500 . ? C104 C105 1.391(4) . ? C104 H104 0.9500 . ? C105 C106 1.481(4) . ? C106 C107 1.385(5) . ? C107 C108 1.381(5) . ? C107 H107 0.9500 . ? C108 C109 1.366(5) . ? C108 H108 0.9500 . ? C109 C110 1.364(5) . ? C109 H109 0.9500 . ? C110 H110 0.9500 . ? N200 C205 1.366(6) . ? N200 C201 1.415(13) . ? C201 C202 1.323(15) . ? C201 H201 0.9500 . ? C202 C203 1.383(13) . ? C202 H202 0.9500 . ? C203 C204 1.336(12) . ? C203 H203 0.9500 . ? C204 C205 1.367(10) . ? C204 H204 0.9500 . ? C205 C205 1.462(13) 2_776 ? N300 C301 1.171(11) . ? C301 C302 1.360(10) . ? C302 H30A 0.9800 . ? C302 H30B 0.9800 . ? C302 H30C 0.9800 . ? 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 C2 O2 C1 115.4(2) . . ? C11 O4 C12 116.2(2) . . ? C14 O6 C13 115.4(2) . . ? C23 O8 C24 116.1(2) . . ? C2 N1 C3 128.3(3) . . ? C2 N1 H1N 116(2) . . ? C3 N1 H1N 115(2) . . ? C3 N2 C4 130.5(3) . . ? C3 N2 H2N 115(2) . . ? C4 N2 H2N 113(2) . . ? C10 N3 C9 122.0(2) . . ? C10 N3 H3N 119(2) . . ? C9 N3 H3N 119(2) . . ? C10 N4 C11 127.1(2) . . ? C10 N4 H4N 119(2) . . ? C11 N4 H4N 113(2) . . ? C14 N5 C15 128.0(2) . . ? C14 N5 H5N 119(2) . . ? C15 N5 H5N 113(2) . . ? C15 N6 C16 132.7(3) . . ? C15 N6 H6N 113(2) . . ? C16 N6 H6N 114(2) . . ? C22 N7 C21 121.3(2) . . ? C22 N7 H7N 120(2) . . ? C21 N7 H7N 119(2) . . ? C22 N8 C23 127.6(2) . . ? C22 N8 H8N 119(2) . . ? C23 N8 H8N 113(2) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 125.0(3) . . ? O1 C2 N1 125.7(3) . . ? O2 C2 N1 109.3(3) . . ? N2 C3 N1 114.0(3) . . ? N2 C3 S1 128.0(2) . . ? N1 C3 S1 118.0(2) . . ? C5 C4 C9 118.9(2) . . ? C5 C4 N2 125.1(2) . . ? C9 C4 N2 116.0(2) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.9(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 120.6(3) . . ? C8 C9 N3 120.6(2) . . ? C4 C9 N3 118.8(2) . . ? N3 C10 N4 117.3(2) . . ? N3 C10 S2 123.1(2) . . ? N4 C10 S2 119.5(2) . . ? O3 C11 O4 125.7(3) . . ? O3 C11 N4 126.1(3) . . ? O4 C11 N4 108.3(2) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O6 C13 H13A 109.5 . . ? O6 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O6 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 O6 123.9(3) . . ? O5 C14 N5 125.8(3) . . ? O6 C14 N5 110.3(2) . . ? N6 C15 N5 114.7(3) . . ? N6 C15 S3 128.1(2) . . ? N5 C15 S3 117.2(2) . . ? C17 C16 C21 118.3(3) . . ? C17 C16 N6 126.3(3) . . ? C21 C16 N6 115.5(2) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 120.8(3) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 119.7(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C21 C20 C19 119.8(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C16 121.2(3) . . ? C20 C21 N7 120.2(2) . . ? C16 C21 N7 118.6(2) . . ? N7 C22 N8 117.4(2) . . ? N7 C22 S4 123.0(2) . . ? N8 C22 S4 119.6(2) . . ? O7 C23 O8 125.9(3) . . ? O7 C23 N8 126.0(3) . . ? O8 C23 N8 108.1(2) . . ? O8 C24 H24A 109.5 . . ? O8 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O8 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C101 N101 C105 116.7(3) . . ? C106 N102 C110 117.8(3) . . ? N101 C101 C102 124.6(3) . . ? N101 C101 H101 117.7 . . ? C102 C101 H101 117.7 . . ? C103 C102 C101 118.4(3) . . ? C103 C102 H102 120.8 . . ? C101 C102 H102 120.8 . . ? C102 C103 C104 118.9(3) . . ? C102 C103 H103 120.5 . . ? C104 C103 H103 120.5 . . ? C103 C104 C105 119.1(3) . . ? C103 C104 H104 120.5 . . ? C105 C104 H104 120.5 . . ? N101 C105 C104 122.2(3) . . ? N101 C105 C106 116.6(3) . . ? C104 C105 C106 121.2(3) . . ? N102 C106 C107 121.4(3) . . ? N102 C106 C105 116.5(3) . . ? C107 C106 C105 122.0(3) . . ? C108 C107 C106 119.2(3) . . ? C108 C107 H107 120.4 . . ? C106 C107 H107 120.4 . . ? C109 C108 C107 119.5(4) . . ? C109 C108 H108 120.3 . . ? C107 C108 H108 120.3 . . ? C110 C109 C108 117.9(3) . . ? C110 C109 H109 121.1 . . ? C108 C109 H109 121.1 . . ? N102 C110 C109 124.2(3) . . ? N102 C110 H110 117.9 . . ? C109 C110 H110 117.9 . . ? C205 N200 C201 114.1(7) . . ? C202 C201 N200 122.4(9) . . ? C202 C201 H201 118.8 . . ? N200 C201 H201 118.8 . . ? C201 C202 C203 121.4(13) . . ? C201 C202 H202 119.3 . . ? C203 C202 H202 119.3 . . ? C204 C203 C202 118.1(11) . . ? C204 C203 H203 121.0 . . ? C202 C203 H203 121.0 . . ? C203 C204 C205 120.6(7) . . ? C203 C204 H204 119.7 . . ? C205 C204 H204 119.7 . . ? N200 C205 C204 123.5(7) . . ? N200 C205 C205 116.4(8) . 2_776 ? C204 C205 C205 120.0(6) . 2_776 ? N300 C301 C302 168.2(15) . . ? C301 C302 H30A 109.5 . . ? C301 C302 H30B 109.5 . . ? H30A C302 H30B 109.5 . . ? C301 C302 H30C 109.5 . . ? H30A C302 H30C 109.5 . . ? H30B C302 H30C 109.5 . . ? 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 C1 O2 C2 O1 -0.2(5) . . . . ? C1 O2 C2 N1 -179.4(3) . . . . ? C3 N1 C2 O1 7.3(5) . . . . ? C3 N1 C2 O2 -173.5(3) . . . . ? C4 N2 C3 N1 175.6(3) . . . . ? C4 N2 C3 S1 -4.7(5) . . . . ? C2 N1 C3 N2 -7.6(5) . . . . ? C2 N1 C3 S1 172.7(3) . . . . ? C3 N2 C4 C5 20.9(5) . . . . ? C3 N2 C4 C9 -160.9(3) . . . . ? C9 C4 C5 C6 3.1(4) . . . . ? N2 C4 C5 C6 -178.7(3) . . . . ? C4 C5 C6 C7 -0.2(5) . . . . ? C5 C6 C7 C8 -2.2(4) . . . . ? C6 C7 C8 C9 1.6(4) . . . . ? C7 C8 C9 C4 1.4(4) . . . . ? C7 C8 C9 N3 -177.8(2) . . . . ? C5 C4 C9 C8 -3.7(4) . . . . ? N2 C4 C9 C8 177.9(2) . . . . ? C5 C4 C9 N3 175.4(3) . . . . ? N2 C4 C9 N3 -2.9(4) . . . . ? C10 N3 C9 C8 -86.7(3) . . . . ? C10 N3 C9 C4 94.1(3) . . . . ? C9 N3 C10 N4 -173.8(2) . . . . ? C9 N3 C10 S2 5.3(4) . . . . ? C11 N4 C10 N3 7.2(4) . . . . ? C11 N4 C10 S2 -172.0(2) . . . . ? C12 O4 C11 O3 5.7(4) . . . . ? C12 O4 C11 N4 -175.4(2) . . . . ? C10 N4 C11 O3 -12.7(4) . . . . ? C10 N4 C11 O4 168.5(2) . . . . ? C13 O6 C14 O5 4.6(4) . . . . ? C13 O6 C14 N5 -175.9(3) . . . . ? C15 N5 C14 O5 -7.6(5) . . . . ? C15 N5 C14 O6 172.9(3) . . . . ? C16 N6 C15 N5 178.9(3) . . . . ? C16 N6 C15 S3 -2.3(5) . . . . ? C14 N5 C15 N6 8.2(5) . . . . ? C14 N5 C15 S3 -170.8(3) . . . . ? C15 N6 C16 C17 -7.7(5) . . . . ? C15 N6 C16 C21 174.1(3) . . . . ? C21 C16 C17 C18 1.8(4) . . . . ? N6 C16 C17 C18 -176.3(3) . . . . ? C16 C17 C18 C19 -0.1(5) . . . . ? C17 C18 C19 C20 -1.5(5) . . . . ? C18 C19 C20 C21 1.3(4) . . . . ? C19 C20 C21 C16 0.5(4) . . . . ? C19 C20 C21 N7 -179.1(3) . . . . ? C17 C16 C21 C20 -2.0(4) . . . . ? N6 C16 C21 C20 176.3(3) . . . . ? C17 C16 C21 N7 177.5(3) . . . . ? N6 C16 C21 N7 -4.1(4) . . . . ? C22 N7 C21 C20 90.5(3) . . . . ? C22 N7 C21 C16 -89.0(3) . . . . ? C21 N7 C22 N8 172.8(2) . . . . ? C21 N7 C22 S4 -6.2(4) . . . . ? C23 N8 C22 N7 -6.0(4) . . . . ? C23 N8 C22 S4 173.1(2) . . . . ? C24 O8 C23 O7 1.6(4) . . . . ? C24 O8 C23 N8 -178.6(2) . . . . ? C22 N8 C23 O7 13.8(5) . . . . ? C22 N8 C23 O8 -166.0(2) . . . . ? C105 N101 C101 C102 -0.8(6) . . . . ? N101 C101 C102 C103 1.2(6) . . . . ? C101 C102 C103 C104 0.0(5) . . . . ? C102 C103 C104 C105 -1.4(5) . . . . ? C101 N101 C105 C104 -0.8(5) . . . . ? C101 N101 C105 C106 178.9(3) . . . . ? C103 C104 C105 N101 1.8(5) . . . . ? C103 C104 C105 C106 -177.8(3) . . . . ? C110 N102 C106 C107 0.3(5) . . . . ? C110 N102 C106 C105 -179.9(3) . . . . ? N101 C105 C106 N102 170.6(3) . . . . ? C104 C105 C106 N102 -9.7(4) . . . . ? N101 C105 C106 C107 -9.6(5) . . . . ? C104 C105 C106 C107 170.1(3) . . . . ? N102 C106 C107 C108 -0.8(5) . . . . ? C105 C106 C107 C108 179.4(3) . . . . ? C106 C107 C108 C109 0.6(6) . . . . ? C107 C108 C109 C110 0.1(6) . . . . ? C106 N102 C110 C109 0.4(5) . . . . ? C108 C109 C110 N102 -0.6(6) . . . . ? C205 N200 C201 C202 0.0(11) . . . . ? N200 C201 C202 C203 -0.4(14) . . . . ? C201 C202 C203 C204 0.1(13) . . . . ? C202 C203 C204 C205 0.6(10) . . . . ? C201 N200 C205 C204 0.7(7) . . . . ? C201 N200 C205 C205 -179.2(5) . . . 2_776 ? C203 C204 C205 N200 -1.0(9) . . . . ? C203 C204 C205 C205 178.9(6) . . . 2_776 ? 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 N1 H1N O6 0.897(18) 2.31(2) 3.189(3) 167(3) . N2 H2N O1 0.877(18) 1.93(3) 2.664(3) 141(3) . N2 H2N N3 0.877(18) 2.25(3) 2.713(3) 113(2) . N3 H3N O3 0.890(18) 2.04(3) 2.707(3) 130(3) . N3 H3N O7 0.890(18) 2.38(3) 3.074(3) 135(3) 2_676 N4 H4N S4 0.888(18) 2.410(19) 3.291(2) 171(3) 2_776 N5 H5N S1 0.897(18) 2.413(19) 3.309(2) 176(3) . N6 H6N O5 0.884(18) 1.91(2) 2.672(3) 143(3) . N6 H6N N7 0.884(18) 2.24(3) 2.695(3) 112(2) . N7 H7N O7 0.890(18) 2.05(3) 2.722(3) 131(3) . N7 H7N O3 0.890(18) 2.38(3) 3.024(3) 130(2) 2_676 N8 H8N S2 0.917(18) 2.412(19) 3.323(2) 172(3) 2_776 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 66.97 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.445 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.057 data_TE-22bp _database_code_depnum_ccdc_archive 'CCDC 831124' #TrackingRef '- bp_bpe_co-crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, 0.5(C10 H8 N2)' _chemical_formula_sum 'C19 H22 N5 O4 S2' _chemical_formula_weight 448.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3860(7) _cell_length_b 17.2950(12) _cell_length_c 15.4566(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.935(3) _cell_angle_gamma 90.00 _cell_volume 2214.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 2.482 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6366 _exptl_absorpt_correction_T_max 0.6366 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6504 _diffrn_reflns_av_R_equivalents 0.0975 _diffrn_reflns_av_sigmaI/netI 0.0931 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.34 _diffrn_reflns_theta_max 66.92 _reflns_number_total 3778 _reflns_number_gt 2565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0966P)^2^+2.2848P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3778 _refine_ls_number_parameters 286 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.2117 _refine_ls_wR_factor_gt 0.1812 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.18262(13) 0.36578(7) 0.19697(8) 0.0497(4) Uani 1 1 d . . . S2 S 0.33515(14) 0.34122(8) -0.16632(9) 0.0595(5) Uani 1 1 d . . . O1 O 0.6156(4) 0.26796(19) 0.0879(2) 0.0545(9) Uani 1 1 d . . . O2 O 0.6247(3) 0.18855(18) 0.2035(2) 0.0462(8) Uani 1 1 d . . . O3 O -0.1228(4) 0.26057(18) -0.0687(2) 0.0506(8) Uani 1 1 d . . . O4 O -0.1156(3) 0.16891(17) -0.1710(2) 0.0454(8) Uani 1 1 d . . . N1 N 0.4297(4) 0.2749(2) 0.1818(2) 0.0373(8) Uani 1 1 d D . . H1N H 0.400(5) 0.251(2) 0.229(2) 0.045 Uiso 1 1 d D . . N2 N 0.3796(4) 0.37105(19) 0.0782(2) 0.0356(8) Uani 1 1 d D . . H2N H 0.461(4) 0.347(2) 0.057(3) 0.043 Uiso 1 1 d D . . N3 N 0.1178(4) 0.3628(2) -0.0622(2) 0.0361(8) Uani 1 1 d D . . H3N H 0.029(4) 0.347(2) -0.042(3) 0.043 Uiso 1 1 d D . . N4 N 0.0802(4) 0.2555(2) -0.1522(2) 0.0398(9) Uani 1 1 d D . . H4N H 0.121(5) 0.225(2) -0.192(2) 0.048 Uiso 1 1 d D . . C1 C 0.8153(7) 0.0886(3) 0.2417(4) 0.0632(15) Uani 1 1 d . . . H1A H 0.8214 0.1085 0.3015 0.095 Uiso 1 1 calc R . . H1B H 0.9210 0.0685 0.2333 0.095 Uiso 1 1 calc R . . H1C H 0.7351 0.0470 0.2322 0.095 Uiso 1 1 calc R . . C2 C 0.7670(5) 0.1520(3) 0.1781(3) 0.0528(12) Uani 1 1 d . . . H2A H 0.8556 0.1901 0.1799 0.063 Uiso 1 1 calc R . . H2B H 0.7419 0.1311 0.1180 0.063 Uiso 1 1 calc R . . C3 C 0.5627(5) 0.2454(3) 0.1513(3) 0.0417(10) Uani 1 1 d . . . C4 C 0.3371(5) 0.3378(2) 0.1480(3) 0.0349(9) Uani 1 1 d . . . C5 C 0.3074(4) 0.4399(2) 0.0392(3) 0.0319(9) Uani 1 1 d . . . C6 C 0.3661(5) 0.5114(2) 0.0692(3) 0.0368(9) Uani 1 1 d . . . H6 H 0.4496 0.5145 0.1182 0.044 Uiso 1 1 calc R . . C7 C 0.3040(5) 0.5783(2) 0.0283(3) 0.0335(9) Uani 1 1 d . . . H7 H 0.3427 0.6272 0.0504 0.040 Uiso 1 1 calc R . . C8 C 0.1858(5) 0.5745(2) -0.0444(3) 0.0355(9) Uani 1 1 d . . . H8 H 0.1456 0.6203 -0.0738 0.043 Uiso 1 1 calc R . . C9 C 0.1264(5) 0.5027(2) -0.0741(3) 0.0349(9) Uani 1 1 d . . . H9 H 0.0434 0.4998 -0.1234 0.042 Uiso 1 1 calc R . . C10 C 0.1861(5) 0.4358(2) -0.0330(3) 0.0336(9) Uani 1 1 d . . . C11 C 0.1703(5) 0.3204(2) -0.1232(3) 0.0364(9) Uani 1 1 d . . . C12 C -0.0595(5) 0.2308(2) -0.1244(3) 0.0396(10) Uani 1 1 d . . . C13 C -0.2630(5) 0.1362(3) -0.1491(3) 0.0494(12) Uani 1 1 d . . . H13A H -0.3510 0.1748 -0.1582 0.059 Uiso 1 1 calc R . . H13B H -0.2470 0.1196 -0.0870 0.059 Uiso 1 1 calc R . . C14 C -0.3042(6) 0.0680(3) -0.2084(4) 0.0635(15) Uani 1 1 d . . . H14A H -0.3044 0.0838 -0.2693 0.095 Uiso 1 1 calc R . . H14B H -0.4112 0.0484 -0.2016 0.095 Uiso 1 1 calc R . . H14C H -0.2237 0.0271 -0.1930 0.095 Uiso 1 1 calc R . . N100 N 0.1861(7) 0.4966(4) 0.4579(4) 0.109(2) Uani 1 1 d . . . C100 C 0.3088(11) 0.4483(8) 0.4538(6) 0.148(4) Uani 1 1 d . . . H100 H 0.3919 0.4647 0.4226 0.177 Uiso 1 1 calc R . . C101 C 0.3222(11) 0.3792(6) 0.4903(7) 0.118(3) Uani 1 1 d . . . H101 H 0.4143 0.3482 0.4864 0.142 Uiso 1 1 calc R . . C102 C 0.2068(10) 0.3530(4) 0.5328(6) 0.109(3) Uani 1 1 d . . . H102 H 0.2124 0.3024 0.5570 0.130 Uiso 1 1 calc R . . C103 C 0.0729(8) 0.4035(4) 0.5409(5) 0.085(2) Uani 1 1 d . . . H103 H -0.0086 0.3889 0.5741 0.102 Uiso 1 1 calc R . . C104 C 0.0682(6) 0.4724(3) 0.4991(3) 0.0514(12) 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 S1 0.0471(6) 0.0508(7) 0.0567(7) 0.0218(6) 0.0252(5) 0.0176(5) S2 0.0516(7) 0.0613(8) 0.0736(9) -0.0350(7) 0.0350(6) -0.0250(6) O1 0.0596(19) 0.053(2) 0.058(2) 0.0228(17) 0.0326(17) 0.0202(16) O2 0.0465(17) 0.0457(18) 0.0487(17) 0.0118(15) 0.0144(14) 0.0178(14) O3 0.0506(18) 0.0417(18) 0.066(2) -0.0101(16) 0.0284(16) -0.0087(14) O4 0.0430(16) 0.0400(17) 0.0558(19) -0.0102(15) 0.0157(14) -0.0125(13) N1 0.0388(18) 0.035(2) 0.0404(19) 0.0116(16) 0.0142(15) 0.0078(15) N2 0.0411(19) 0.0299(18) 0.0388(19) 0.0060(15) 0.0149(15) 0.0067(15) N3 0.0359(18) 0.0347(19) 0.0407(19) -0.0056(16) 0.0157(15) -0.0043(15) N4 0.0406(19) 0.0327(19) 0.050(2) -0.0121(16) 0.0187(16) -0.0071(15) C1 0.072(3) 0.061(3) 0.059(3) 0.010(3) 0.016(3) 0.030(3) C2 0.052(3) 0.052(3) 0.058(3) 0.009(2) 0.021(2) 0.021(2) C3 0.038(2) 0.039(2) 0.050(3) 0.007(2) 0.010(2) 0.0046(19) C4 0.035(2) 0.030(2) 0.040(2) 0.0041(18) 0.0066(17) 0.0012(17) C5 0.036(2) 0.028(2) 0.034(2) 0.0025(17) 0.0127(17) 0.0027(16) C6 0.035(2) 0.042(2) 0.034(2) -0.0012(19) 0.0086(17) 0.0013(18) C7 0.035(2) 0.030(2) 0.038(2) -0.0003(17) 0.0123(17) -0.0011(16) C8 0.037(2) 0.034(2) 0.037(2) 0.0044(18) 0.0090(17) 0.0028(17) C9 0.036(2) 0.036(2) 0.033(2) -0.0019(18) 0.0075(17) 0.0037(18) C10 0.034(2) 0.029(2) 0.040(2) -0.0049(17) 0.0129(17) -0.0002(17) C11 0.041(2) 0.031(2) 0.038(2) -0.0018(18) 0.0112(18) -0.0034(18) C12 0.037(2) 0.035(2) 0.049(3) -0.005(2) 0.0122(19) -0.0024(18) C13 0.042(2) 0.048(3) 0.059(3) -0.002(2) 0.013(2) -0.012(2) C14 0.061(3) 0.061(3) 0.070(3) -0.011(3) 0.015(3) -0.026(3) N100 0.092(4) 0.138(6) 0.106(5) 0.042(4) 0.044(4) 0.034(4) C100 0.122(7) 0.218(13) 0.116(7) 0.041(8) 0.059(6) 0.089(8) C101 0.096(6) 0.100(7) 0.154(9) -0.029(6) 0.006(6) 0.037(5) C102 0.104(5) 0.059(4) 0.145(8) 0.033(5) -0.038(5) 0.004(4) C103 0.074(4) 0.074(4) 0.103(5) 0.042(4) 0.001(4) 0.000(3) C104 0.053(3) 0.055(3) 0.045(3) 0.004(2) 0.006(2) -0.004(2) _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 S1 C4 1.670(4) . ? S2 C11 1.664(4) . ? O1 C3 1.201(5) . ? O2 C3 1.326(5) . ? O2 C2 1.457(5) . ? O3 C12 1.196(5) . ? O4 C12 1.334(5) . ? O4 C13 1.447(5) . ? N1 C3 1.375(5) . ? N1 C4 1.390(5) . ? N1 H1N 0.908(19) . ? N2 C4 1.320(5) . ? N2 C5 1.426(5) . ? N2 H2N 0.902(19) . ? N3 C11 1.323(5) . ? N3 C10 1.431(5) . ? N3 H3N 0.898(19) . ? N4 C12 1.377(5) . ? N4 C11 1.388(5) . ? N4 H4N 0.911(19) . ? C1 C2 1.486(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.385(6) . ? C5 C10 1.390(6) . ? C6 C7 1.381(6) . ? C6 H6 0.9500 . ? C7 C8 1.380(6) . ? C7 H7 0.9500 . ? C8 C9 1.388(6) . ? C8 H8 0.9500 . ? C9 C10 1.377(6) . ? C9 H9 0.9500 . ? C13 C14 1.502(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N100 C104 1.325(7) . ? N100 C100 1.335(10) . ? C100 C101 1.319(13) . ? C100 H100 0.9500 . ? C101 C102 1.330(13) . ? C101 H101 0.9500 . ? C102 C103 1.444(10) . ? C102 H102 0.9500 . ? C103 C104 1.353(7) . ? C103 H103 0.9500 . ? C104 C104 1.493(10) 3_566 ? 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 C3 O2 C2 114.7(3) . . ? C12 O4 C13 115.4(3) . . ? C3 N1 C4 126.6(3) . . ? C3 N1 H1N 116(3) . . ? C4 N1 H1N 117(3) . . ? C4 N2 C5 124.0(3) . . ? C4 N2 H2N 114(3) . . ? C5 N2 H2N 122(3) . . ? C11 N3 C10 123.6(3) . . ? C11 N3 H3N 118(3) . . ? C10 N3 H3N 118(3) . . ? C12 N4 C11 126.7(4) . . ? C12 N4 H4N 117(3) . . ? C11 N4 H4N 116(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 107.0(4) . . ? O2 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? O2 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.6 . . ? O1 C3 O2 125.3(4) . . ? O1 C3 N1 125.5(4) . . ? O2 C3 N1 109.2(4) . . ? N2 C4 N1 116.2(3) . . ? N2 C4 S1 124.8(3) . . ? N1 C4 S1 118.9(3) . . ? C6 C5 C10 119.5(4) . . ? C6 C5 N2 119.9(4) . . ? C10 C5 N2 120.5(3) . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.3(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.2(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 120.8(4) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C5 119.8(4) . . ? C9 C10 N3 119.8(4) . . ? C5 C10 N3 120.3(3) . . ? N3 C11 N4 117.0(3) . . ? N3 C11 S2 123.7(3) . . ? N4 C11 S2 119.4(3) . . ? O3 C12 O4 125.1(4) . . ? O3 C12 N4 125.8(4) . . ? O4 C12 N4 109.0(4) . . ? O4 C13 C14 106.7(4) . . ? O4 C13 H13A 110.4 . . ? C14 C13 H13A 110.4 . . ? O4 C13 H13B 110.4 . . ? C14 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C104 N100 C100 117.6(8) . . ? C101 C100 N100 124.2(9) . . ? C101 C100 H100 117.9 . . ? N100 C100 H100 117.9 . . ? C100 C101 C102 120.0(8) . . ? C100 C101 H101 120.0 . . ? C102 C101 H101 120.0 . . ? C101 C102 C103 118.2(7) . . ? C101 C102 H102 120.9 . . ? C103 C102 H102 120.9 . . ? C104 C103 C102 117.1(6) . . ? C104 C103 H103 121.4 . . ? C102 C103 H103 121.4 . . ? N100 C104 C103 122.7(6) . . ? N100 C104 C104 115.9(6) . 3_566 ? C103 C104 C104 121.3(6) . 3_566 ? 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 C3 O2 C2 C1 -178.0(4) . . . . ? C2 O2 C3 O1 -0.8(7) . . . . ? C2 O2 C3 N1 179.9(4) . . . . ? C4 N1 C3 O1 -3.2(8) . . . . ? C4 N1 C3 O2 176.1(4) . . . . ? C5 N2 C4 N1 -174.6(4) . . . . ? C5 N2 C4 S1 5.5(6) . . . . ? C3 N1 C4 N2 1.8(6) . . . . ? C3 N1 C4 S1 -178.3(3) . . . . ? C4 N2 C5 C6 87.2(5) . . . . ? C4 N2 C5 C10 -97.5(5) . . . . ? C10 C5 C6 C7 0.6(6) . . . . ? N2 C5 C6 C7 175.9(3) . . . . ? C5 C6 C7 C8 -1.9(6) . . . . ? C6 C7 C8 C9 2.2(6) . . . . ? C7 C8 C9 C10 -1.3(6) . . . . ? C8 C9 C10 C5 0.0(6) . . . . ? C8 C9 C10 N3 177.1(3) . . . . ? C6 C5 C10 C9 0.3(6) . . . . ? N2 C5 C10 C9 -174.9(3) . . . . ? C6 C5 C10 N3 -176.7(3) . . . . ? N2 C5 C10 N3 8.0(6) . . . . ? C11 N3 C10 C9 89.9(5) . . . . ? C11 N3 C10 C5 -93.0(5) . . . . ? C10 N3 C11 N4 -172.5(4) . . . . ? C10 N3 C11 S2 7.1(6) . . . . ? C12 N4 C11 N3 0.5(6) . . . . ? C12 N4 C11 S2 -179.1(4) . . . . ? C13 O4 C12 O3 -1.4(6) . . . . ? C13 O4 C12 N4 180.0(4) . . . . ? C11 N4 C12 O3 -2.2(8) . . . . ? C11 N4 C12 O4 176.4(4) . . . . ? C12 O4 C13 C14 -179.9(4) . . . . ? C104 N100 C100 C101 -2.1(16) . . . . ? N100 C100 C101 C102 1.7(18) . . . . ? C100 C101 C102 C103 -2.9(15) . . . . ? C101 C102 C103 C104 4.6(12) . . . . ? C100 N100 C104 C103 4.0(11) . . . . ? C100 N100 C104 C104 -179.0(8) . . . 3_566 ? C102 C103 C104 N100 -5.2(10) . . . . ? C102 C103 C104 C104 177.9(6) . . . 3_566 ? 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 N1 H1N S2 0.908(19) 2.39(2) 3.279(4) 165(4) 4_566 N2 H2N O1 0.902(19) 1.89(3) 2.650(4) 140(4) . N3 H3N O3 0.898(19) 1.97(3) 2.673(4) 134(4) . N4 H4N S1 0.911(19) 2.44(2) 3.346(4) 170(4) 4_565 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 66.92 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.434 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.078 data_TM-44bp _database_code_depnum_ccdc_archive 'CCDC 831125' #TrackingRef '- bp_bpe_co-crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N4 O4 S2, 0.5(C10 H8 N2)' _chemical_formula_sum 'C17 H18 N5 O4 S2' _chemical_formula_weight 420.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0382(2) _cell_length_b 9.5723(2) _cell_length_c 12.5370(3) _cell_angle_alpha 100.183(3) _cell_angle_beta 104.203(3) _cell_angle_gamma 101.444(3) _cell_volume 1001.16(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 438 _exptl_absorpt_coefficient_mu 2.709 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6133 _exptl_absorpt_correction_T_max 0.6133 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4322 _diffrn_reflns_av_R_equivalents 0.1194 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 66.54 _reflns_number_total 3298 _reflns_number_gt 2873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1243P)^2^+0.4900P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3298 _refine_ls_number_parameters 268 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1788 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.39585(9) 0.69609(8) 0.33764(8) 0.0421(3) Uani 1 1 d . . . S2 S -0.19367(11) 0.18904(9) 0.24015(7) 0.0510(3) Uani 1 1 d . . . O1 O 0.2680(2) 0.2157(2) 0.3609(2) 0.0470(6) Uani 1 1 d . . . O2 O 0.5204(2) 0.2323(2) 0.3591(2) 0.0447(6) Uani 1 1 d . . . O3 O -0.0429(3) 0.3408(2) -0.05209(19) 0.0423(6) Uani 1 1 d . . . O4 O -0.1149(3) 0.0941(2) -0.12686(18) 0.0403(6) Uani 1 1 d . . . N1 N 0.4296(3) 0.4309(3) 0.3540(2) 0.0332(6) Uani 1 1 d D . . H1N H 0.526(3) 0.469(4) 0.353(3) 0.040 Uiso 1 1 d D . . N2 N 0.1826(3) 0.4664(3) 0.3500(2) 0.0323(6) Uani 1 1 d D . . H2N H 0.163(4) 0.374(2) 0.354(3) 0.039 Uiso 1 1 d D . . N3 N -0.0819(3) 0.4107(3) 0.1573(2) 0.0332(6) Uani 1 1 d D . . H3N H -0.048(4) 0.447(4) 0.103(2) 0.040 Uiso 1 1 d D . . N4 N -0.1510(3) 0.1754(3) 0.0386(2) 0.0344(6) Uani 1 1 d D . . H4N H -0.199(4) 0.082(2) 0.030(3) 0.041 Uiso 1 1 d D . . C1 C 0.4979(4) 0.0773(4) 0.3592(4) 0.0549(10) Uani 1 1 d . . . H1A H 0.4600 0.0589 0.4235 0.082 Uiso 1 1 calc R . . H1B H 0.5985 0.0506 0.3658 0.082 Uiso 1 1 calc R . . H1C H 0.4202 0.0180 0.2885 0.082 Uiso 1 1 calc R . . C2 C 0.3947(3) 0.2853(3) 0.3583(3) 0.0346(7) Uani 1 1 d . . . C3 C 0.3289(3) 0.5245(3) 0.3481(2) 0.0309(7) Uani 1 1 d . . . C4 C 0.0651(3) 0.5474(3) 0.3528(2) 0.0294(6) Uani 1 1 d . . . C5 C 0.0793(3) 0.6501(3) 0.4513(2) 0.0323(7) Uani 1 1 d . . . H5 H 0.1700 0.6712 0.5147 0.039 Uiso 1 1 calc R . . C6 C -0.0393(3) 0.7212(3) 0.4565(3) 0.0360(7) Uani 1 1 d . . . H6 H -0.0285 0.7929 0.5228 0.043 Uiso 1 1 calc R . . C7 C -0.1742(3) 0.6878(4) 0.3647(3) 0.0377(7) Uani 1 1 d . . . H7 H -0.2560 0.7357 0.3685 0.045 Uiso 1 1 calc R . . C8 C -0.1888(3) 0.5839(3) 0.2671(3) 0.0361(7) Uani 1 1 d . . . H8 H -0.2812 0.5606 0.2048 0.043 Uiso 1 1 calc R . . C9 C -0.0690(3) 0.5136(3) 0.2602(2) 0.0298(6) Uani 1 1 d . . . C10 C -0.1386(3) 0.2662(3) 0.1418(3) 0.0333(7) Uani 1 1 d . . . C11 C -0.0971(3) 0.2154(3) -0.0483(3) 0.0332(7) Uani 1 1 d . . . C12 C -0.0511(4) 0.1177(4) -0.2204(3) 0.0423(8) Uani 1 1 d . . . H12A H -0.1066 0.1790 -0.2617 0.063 Uiso 1 1 calc R . . H12B H -0.0655 0.0229 -0.2718 0.063 Uiso 1 1 calc R . . H12C H 0.0616 0.1670 -0.1904 0.063 Uiso 1 1 calc R . . N100 N 0.3296(3) 0.1314(3) 0.0070(2) 0.0415(7) Uani 1 1 d . . . C101 C 0.4656(3) 0.4231(3) 0.0022(2) 0.0320(7) Uani 1 1 d . . . C102 C 0.5064(4) 0.3028(4) -0.0528(3) 0.0434(8) Uani 1 1 d . . . H102 H 0.5825 0.3177 -0.0930 0.052 Uiso 1 1 calc R . . C103 C 0.4360(4) 0.1613(4) -0.0492(3) 0.0467(8) Uani 1 1 d . . . H103 H 0.4650 0.0816 -0.0885 0.056 Uiso 1 1 calc R . . C104 C 0.3547(4) 0.3912(4) 0.0611(3) 0.0391(7) Uani 1 1 d . . . H104 H 0.3218 0.4682 0.1002 0.047 Uiso 1 1 calc R . . C105 C 0.2929(4) 0.2464(3) 0.0622(3) 0.0408(8) Uani 1 1 d . . . H105 H 0.2203 0.2281 0.1046 0.049 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 S1 0.0369(5) 0.0335(5) 0.0640(6) 0.0180(4) 0.0253(4) 0.0080(3) S2 0.0717(6) 0.0394(5) 0.0369(5) 0.0093(4) 0.0246(4) -0.0085(4) O1 0.0371(12) 0.0346(12) 0.0728(17) 0.0130(11) 0.0240(11) 0.0063(10) O2 0.0405(12) 0.0377(13) 0.0680(16) 0.0218(11) 0.0257(11) 0.0167(10) O3 0.0591(14) 0.0251(11) 0.0400(13) 0.0059(9) 0.0219(11) -0.0033(9) O4 0.0559(13) 0.0285(11) 0.0344(12) 0.0039(9) 0.0205(10) -0.0002(9) N1 0.0282(12) 0.0317(13) 0.0410(15) 0.0099(11) 0.0142(10) 0.0042(10) N2 0.0288(12) 0.0277(13) 0.0412(14) 0.0075(11) 0.0145(10) 0.0040(10) N3 0.0396(13) 0.0301(13) 0.0274(13) 0.0056(10) 0.0131(11) 0.0001(10) N4 0.0436(14) 0.0245(12) 0.0330(13) 0.0066(10) 0.0165(11) -0.0029(10) C1 0.059(2) 0.0378(19) 0.083(3) 0.0226(19) 0.034(2) 0.0209(16) C2 0.0342(15) 0.0363(17) 0.0365(17) 0.0092(13) 0.0146(12) 0.0101(13) C3 0.0271(13) 0.0368(16) 0.0286(15) 0.0063(12) 0.0108(11) 0.0055(11) C4 0.0256(13) 0.0294(14) 0.0346(16) 0.0102(12) 0.0123(11) 0.0035(11) C5 0.0298(14) 0.0360(16) 0.0284(15) 0.0076(12) 0.0070(11) 0.0037(12) C6 0.0389(16) 0.0360(17) 0.0344(16) 0.0049(13) 0.0173(13) 0.0075(13) C7 0.0301(14) 0.0433(18) 0.0433(18) 0.0099(14) 0.0162(13) 0.0107(13) C8 0.0276(14) 0.0384(17) 0.0397(17) 0.0114(14) 0.0075(12) 0.0038(12) C9 0.0305(14) 0.0290(15) 0.0294(15) 0.0070(12) 0.0129(11) 0.0014(11) C10 0.0312(14) 0.0328(16) 0.0318(16) 0.0067(12) 0.0096(12) -0.0011(12) C11 0.0364(15) 0.0282(16) 0.0322(16) 0.0052(12) 0.0115(12) 0.0014(12) C12 0.0575(19) 0.0337(17) 0.0388(18) 0.0071(14) 0.0265(15) 0.0047(14) N100 0.0471(15) 0.0309(14) 0.0412(15) 0.0117(12) 0.0108(12) -0.0024(11) C101 0.0306(14) 0.0304(16) 0.0281(15) 0.0112(12) 0.0002(11) -0.0007(12) C102 0.0419(17) 0.0342(17) 0.058(2) 0.0189(15) 0.0202(15) 0.0051(13) C103 0.0506(18) 0.0300(17) 0.063(2) 0.0132(16) 0.0251(17) 0.0056(14) C104 0.0485(17) 0.0312(16) 0.0348(17) 0.0044(13) 0.0171(14) 0.0005(13) C105 0.0432(17) 0.0381(18) 0.0358(17) 0.0091(14) 0.0151(14) -0.0066(14) _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 S1 C3 1.674(3) . ? S2 C10 1.671(3) . ? O1 C2 1.216(4) . ? O2 C2 1.332(4) . ? O2 C1 1.457(4) . ? O3 C11 1.217(4) . ? O4 C11 1.337(4) . ? O4 C12 1.460(4) . ? N1 C2 1.380(4) . ? N1 C3 1.397(4) . ? N1 H1N 0.880(18) . ? N2 C3 1.336(4) . ? N2 C4 1.438(4) . ? N2 H2N 0.882(19) . ? N3 C10 1.337(4) . ? N3 C9 1.441(4) . ? N3 H3N 0.903(18) . ? N4 C11 1.381(4) . ? N4 C10 1.391(4) . ? N4 H4N 0.889(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C4 C9 1.394(4) . ? C4 C5 1.397(4) . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 C7 1.393(4) . ? C6 H6 0.9500 . ? C7 C8 1.393(4) . ? C7 H7 0.9500 . ? C8 C9 1.396(4) . ? C8 H8 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N100 C105 1.337(4) . ? N100 C103 1.340(5) . ? C101 C102 1.397(5) . ? C101 C104 1.402(4) . ? C101 C101 1.496(6) 2_665 ? C102 C103 1.392(5) . ? C102 H102 0.9500 . ? C103 H103 0.9500 . ? C104 C105 1.392(4) . ? C104 H104 0.9500 . ? C105 H105 0.9500 . ? 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 C2 O2 C1 115.6(2) . . ? C11 O4 C12 115.2(2) . . ? C2 N1 C3 127.8(2) . . ? C2 N1 H1N 116(2) . . ? C3 N1 H1N 116(2) . . ? C3 N2 C4 124.1(2) . . ? C3 N2 H2N 115(2) . . ? C4 N2 H2N 121(2) . . ? C10 N3 C9 122.1(2) . . ? C10 N3 H3N 121(2) . . ? C9 N3 H3N 117(2) . . ? C11 N4 C10 127.1(2) . . ? C11 N4 H4N 119(2) . . ? C10 N4 H4N 114(2) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 125.0(3) . . ? O1 C2 N1 125.0(3) . . ? O2 C2 N1 109.9(2) . . ? N2 C3 N1 115.6(3) . . ? N2 C3 S1 125.1(2) . . ? N1 C3 S1 119.3(2) . . ? C9 C4 C5 120.4(3) . . ? C9 C4 N2 119.4(3) . . ? C5 C4 N2 120.0(2) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.1(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.6(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C4 C9 C8 119.1(3) . . ? C4 C9 N3 120.5(3) . . ? C8 C9 N3 120.3(3) . . ? N3 C10 N4 118.2(3) . . ? N3 C10 S2 123.5(2) . . ? N4 C10 S2 118.3(2) . . ? O3 C11 O4 126.1(3) . . ? O3 C11 N4 125.2(3) . . ? O4 C11 N4 108.7(2) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C105 N100 C103 116.5(3) . . ? C102 C101 C104 116.0(3) . . ? C102 C101 C101 122.2(3) . 2_665 ? C104 C101 C101 121.8(4) . 2_665 ? C103 C102 C101 120.3(3) . . ? C103 C102 H102 119.9 . . ? C101 C102 H102 119.9 . . ? N100 C103 C102 123.5(3) . . ? N100 C103 H103 118.3 . . ? C102 C103 H103 118.3 . . ? C105 C104 C101 119.8(3) . . ? C105 C104 H104 120.1 . . ? C101 C104 H104 120.1 . . ? N100 C105 C104 123.9(3) . . ? N100 C105 H105 118.1 . . ? C104 C105 H105 118.1 . . ? 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 C1 O2 C2 O1 2.2(5) . . . . ? C1 O2 C2 N1 -177.8(3) . . . . ? C3 N1 C2 O1 -2.3(5) . . . . ? C3 N1 C2 O2 177.7(3) . . . . ? C4 N2 C3 N1 175.4(3) . . . . ? C4 N2 C3 S1 -5.4(4) . . . . ? C2 N1 C3 N2 2.0(4) . . . . ? C2 N1 C3 S1 -177.2(2) . . . . ? C3 N2 C4 C9 113.8(3) . . . . ? C3 N2 C4 C5 -71.7(4) . . . . ? C9 C4 C5 C6 -1.3(4) . . . . ? N2 C4 C5 C6 -175.7(3) . . . . ? C4 C5 C6 C7 1.6(5) . . . . ? C5 C6 C7 C8 -0.7(5) . . . . ? C6 C7 C8 C9 -0.4(5) . . . . ? C5 C4 C9 C8 0.1(4) . . . . ? N2 C4 C9 C8 174.6(2) . . . . ? C5 C4 C9 N3 178.3(2) . . . . ? N2 C4 C9 N3 -7.2(4) . . . . ? C7 C8 C9 C4 0.7(4) . . . . ? C7 C8 C9 N3 -177.4(3) . . . . ? C10 N3 C9 C4 86.9(3) . . . . ? C10 N3 C9 C8 -94.9(4) . . . . ? C9 N3 C10 N4 178.2(2) . . . . ? C9 N3 C10 S2 -2.3(4) . . . . ? C11 N4 C10 N3 6.7(5) . . . . ? C11 N4 C10 S2 -172.8(2) . . . . ? C12 O4 C11 O3 4.9(5) . . . . ? C12 O4 C11 N4 -175.2(3) . . . . ? C10 N4 C11 O3 -7.4(5) . . . . ? C10 N4 C11 O4 172.7(3) . . . . ? C104 C101 C102 C103 1.2(5) . . . . ? C101 C101 C102 C103 -178.1(3) 2_665 . . . ? C105 N100 C103 C102 -0.6(5) . . . . ? C101 C102 C103 N100 -1.0(6) . . . . ? C102 C101 C104 C105 0.1(4) . . . . ? C101 C101 C104 C105 179.5(3) 2_665 . . . ? C103 N100 C105 C104 2.0(5) . . . . ? C101 C104 C105 N100 -1.8(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 N2 H2N O1 0.882(19) 1.94(3) 2.677(3) 140(3) . N3 H3N O3 0.903(18) 2.05(3) 2.719(3) 130(3) . N3 H3N O3 0.903(18) 2.29(3) 3.074(3) 144(3) 2_565 N4 H4N N100 0.889(19) 2.05(2) 2.937(4) 173(3) 2 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 66.54 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.530 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.114 data_TE-44bp _database_code_depnum_ccdc_archive 'CCDC 831126' #TrackingRef '- bp_bpe_co-crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C10 H8 N2' _chemical_formula_sum 'C24 H26 N6 O4 S2' _chemical_formula_weight 526.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.8193(4) _cell_length_b 12.8098(5) _cell_length_c 26.3527(10) _cell_angle_alpha 91.574(2) _cell_angle_beta 95.655(2) _cell_angle_gamma 100.640(3) _cell_volume 3897.9(2) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 2.212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6078 _exptl_absorpt_correction_T_max 0.6660 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18442 _diffrn_reflns_av_R_equivalents 0.1463 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 67.08 _reflns_number_total 13511 _reflns_number_gt 9678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1463P)^2^+1.9774P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13511 _refine_ls_number_parameters 1021 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1094 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2389 _refine_ls_wR_factor_gt 0.2103 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.06145(9) 0.84758(9) 0.16047(4) 0.0326(3) Uani 1 1 d . . . S2 S 0.53622(8) 0.98099(9) 0.08260(4) 0.0341(3) Uani 1 1 d . . . S3 S 0.58159(9) 0.31077(9) 0.17369(4) 0.0346(3) Uani 1 1 d . . . S4 S 0.12170(8) 0.23473(9) 0.26559(4) 0.0331(3) Uani 1 1 d . . . S5 S 1.20365(9) 0.36595(10) 0.42465(4) 0.0362(3) Uani 1 1 d . . . S6 S 0.72972(9) 0.26303(9) 0.50737(4) 0.0364(3) Uani 1 1 d . . . O1 O 0.1855(2) 0.5355(2) 0.12964(11) 0.0333(7) Uani 1 1 d . . . O2 O -0.0016(2) 0.4859(2) 0.09642(12) 0.0371(8) Uani 1 1 d . . . O3 O 0.1444(2) 0.9008(3) 0.03527(11) 0.0358(7) Uani 1 1 d . . . O4 O 0.2081(2) 0.9578(3) -0.03907(11) 0.0359(7) Uani 1 1 d . . . O5 O 0.4446(2) 0.6210(2) 0.16731(12) 0.0331(7) Uani 1 1 d . . . O6 O 0.6330(2) 0.6895(2) 0.19169(12) 0.0361(7) Uani 1 1 d . . . O7 O 0.5150(3) 0.3269(3) 0.30358(12) 0.0464(9) Uani 1 1 d . . . O8 O 0.4596(2) 0.3524(3) 0.38163(11) 0.0368(7) Uani 1 1 d . . . O9 O 0.8124(3) 0.2691(3) 0.38192(12) 0.0479(9) Uani 1 1 d . . . O10 O 0.8725(3) 0.2641(3) 0.30318(12) 0.0455(9) Uani 1 1 d . . . O11 O 0.8737(2) -0.0405(3) 0.48323(12) 0.0391(8) Uani 1 1 d . . . O12 O 0.6909(3) -0.1006(3) 0.44734(14) 0.0452(9) Uani 1 1 d . A . N1 N 0.0555(3) 0.6504(3) 0.12765(13) 0.0285(8) Uani 1 1 d D . . H1N H -0.0198(19) 0.651(4) 0.1195(17) 0.034 Uiso 1 1 d D . . N2 N 0.2352(3) 0.7413(3) 0.16394(13) 0.0279(8) Uani 1 1 d D . . H2N H 0.260(4) 0.680(2) 0.1612(17) 0.033 Uiso 1 1 d D . . N3 N 0.3225(3) 0.9204(3) 0.11067(13) 0.0283(8) Uani 1 1 d D . . H3N H 0.2454(18) 0.911(4) 0.1014(17) 0.034 Uiso 1 1 d D . . N4 N 0.3374(3) 0.9599(3) 0.02636(13) 0.0306(8) Uani 1 1 d D . . H4N H 0.382(3) 0.976(4) 0.0004(13) 0.037 Uiso 1 1 d D . . N5 N 0.5810(3) 0.5151(3) 0.18393(14) 0.0293(8) Uani 1 1 d D . . H5N H 0.6583(18) 0.520(4) 0.1916(17) 0.035 Uiso 1 1 d D . . N6 N 0.4020(3) 0.4084(3) 0.15959(13) 0.0277(8) Uani 1 1 d D . . H6N H 0.376(4) 0.469(2) 0.1594(17) 0.033 Uiso 1 1 d D . . N7 N 0.3240(3) 0.2902(3) 0.31980(14) 0.0333(8) Uani 1 1 d D . . H7N H 0.277(3) 0.302(4) 0.3438(14) 0.040 Uiso 1 1 d D . . N8 N 0.3332(3) 0.2618(3) 0.23342(13) 0.0288(8) Uani 1 1 d D . . H8N H 0.4078(19) 0.287(4) 0.2424(17) 0.035 Uiso 1 1 d D . . N9 N 1.0038(3) 0.3191(3) 0.36761(14) 0.0324(8) Uani 1 1 d D . . H9N H 1.051(3) 0.311(4) 0.3434(13) 0.039 Uiso 1 1 d D . . N10 N 0.9892(3) 0.3277(3) 0.45427(13) 0.0298(8) Uani 1 1 d D . . H10N H 0.9120(17) 0.318(4) 0.4494(17) 0.036 Uiso 1 1 d D . . N11 N 0.9086(3) 0.1638(3) 0.51616(14) 0.0306(8) Uani 1 1 d D . . H11N H 0.936(4) 0.103(2) 0.5137(18) 0.037 Uiso 1 1 d D . . N12 N 0.7345(3) 0.0648(3) 0.47924(14) 0.0317(8) Uani 1 1 d D . . H12N H 0.6565(18) 0.060(4) 0.4720(18) 0.038 Uiso 1 1 d D . . C1 C 0.0545(5) 0.3761(4) 0.0300(2) 0.0479(13) Uani 1 1 d . . . H1A H -0.0013 0.4020 0.0058 0.072 Uiso 1 1 calc R . . H1B H 0.0582 0.3026 0.0201 0.072 Uiso 1 1 calc R . . H1C H 0.1311 0.4210 0.0298 0.072 Uiso 1 1 calc R . . C2 C 0.0171(4) 0.3801(4) 0.08214(19) 0.0390(11) Uani 1 1 d . . . H2A H -0.0555 0.3278 0.0834 0.047 Uiso 1 1 calc R . . H2B H 0.0771 0.3601 0.1070 0.047 Uiso 1 1 calc R . . C3 C 0.0892(3) 0.5551(3) 0.11921(16) 0.0288(9) Uani 1 1 d . . . C4 C 0.1229(3) 0.7420(3) 0.15068(15) 0.0282(9) Uani 1 1 d . . . C5 C 0.3117(3) 0.8298(3) 0.19038(16) 0.0280(9) Uani 1 1 d . . . C6 C 0.3426(4) 0.8276(4) 0.24244(16) 0.0364(10) Uani 1 1 d . . . H6 H 0.3127 0.7674 0.2606 0.044 Uiso 1 1 calc R . . C7 C 0.4175(4) 0.9135(4) 0.26805(18) 0.0419(12) Uani 1 1 d . . . H7 H 0.4400 0.9116 0.3036 0.050 Uiso 1 1 calc R . . C8 C 0.4591(4) 1.0017(4) 0.24167(17) 0.0372(11) Uani 1 1 d . . . H8 H 0.5086 1.0611 0.2594 0.045 Uiso 1 1 calc R . . C9 C 0.4298(3) 1.0044(4) 0.19023(17) 0.0324(10) Uani 1 1 d . . . H9 H 0.4590 1.0656 0.1725 0.039 Uiso 1 1 calc R . . C10 C 0.3573(3) 0.9181(3) 0.16375(15) 0.0268(9) Uani 1 1 d . . . C11 C 0.3921(3) 0.9523(3) 0.07513(16) 0.0285(9) Uani 1 1 d . . . C12 C 0.2210(3) 0.9350(3) 0.00994(16) 0.0287(9) Uani 1 1 d . . . C13 C 0.0939(3) 0.9253(4) -0.06633(17) 0.0384(11) Uani 1 1 d . . . H13A H 0.0458 0.9795 -0.0611 0.046 Uiso 1 1 calc R . . H13B H 0.0548 0.8568 -0.0541 0.046 Uiso 1 1 calc R . . C14 C 0.1110(4) 0.9138(6) -0.12102(19) 0.0646(18) Uani 1 1 d . . . H14A H 0.1486 0.9824 -0.1326 0.097 Uiso 1 1 calc R . . H14B H 0.0358 0.8905 -0.1411 0.097 Uiso 1 1 calc R . . H14C H 0.1600 0.8610 -0.1255 0.097 Uiso 1 1 calc R . . C15 C 0.7196(5) 0.8710(4) 0.2013(3) 0.0651(18) Uani 1 1 d . . . H15A H 0.7417 0.8657 0.2378 0.098 Uiso 1 1 calc R . . H15B H 0.7092 0.9438 0.1946 0.098 Uiso 1 1 calc R . . H15C H 0.7806 0.8533 0.1818 0.098 Uiso 1 1 calc R . . C16 C 0.6099(4) 0.7960(4) 0.1856(2) 0.0401(11) Uani 1 1 d . . . H16A H 0.5494 0.8088 0.2072 0.048 Uiso 1 1 calc R . . H16B H 0.5827 0.8054 0.1495 0.048 Uiso 1 1 calc R . . C17 C 0.5433(3) 0.6101(3) 0.17988(16) 0.0291(9) Uani 1 1 d . . . C18 C 0.5164(3) 0.4155(3) 0.17201(15) 0.0271(9) Uani 1 1 d . . . C19 C 0.3278(3) 0.3091(3) 0.14473(15) 0.0263(9) Uani 1 1 d . . . C20 C 0.2899(3) 0.2840(4) 0.09359(16) 0.0317(10) Uani 1 1 d . . . H20 H 0.3133 0.3333 0.0686 0.038 Uiso 1 1 calc R . . C21 C 0.2185(4) 0.1881(4) 0.07879(17) 0.0336(10) Uani 1 1 d . . . H21 H 0.1921 0.1719 0.0437 0.040 Uiso 1 1 calc R . . C22 C 0.1850(3) 0.1151(4) 0.11498(17) 0.0331(10) Uani 1 1 d . . . H22 H 0.1379 0.0480 0.1046 0.040 Uiso 1 1 calc R . . C23 C 0.2205(3) 0.1401(4) 0.16627(17) 0.0330(10) Uani 1 1 d . . . H23 H 0.1960 0.0908 0.1911 0.040 Uiso 1 1 calc R . . C24 C 0.2913(3) 0.2364(3) 0.18143(15) 0.0272(9) Uani 1 1 d . . . C25 C 0.2664(3) 0.2625(3) 0.27144(15) 0.0275(9) Uani 1 1 d . . . C26 C 0.4415(4) 0.3238(4) 0.33238(16) 0.0337(10) Uani 1 1 d . . . C27 C 0.5781(4) 0.4018(5) 0.40109(18) 0.0428(12) Uani 1 1 d . . . H27A H 0.6111 0.4560 0.3778 0.051 Uiso 1 1 calc R . . H27B H 0.6280 0.3477 0.4046 0.051 Uiso 1 1 calc R . . C28 C 0.5689(4) 0.4519(5) 0.4518(2) 0.0537(14) Uani 1 1 d . . . H28A H 0.5161 0.5024 0.4478 0.081 Uiso 1 1 calc R . . H28B H 0.6456 0.4894 0.4664 0.081 Uiso 1 1 calc R . . H28C H 0.5390 0.3967 0.4747 0.081 Uiso 1 1 calc R . . C29 C 0.7699(4) 0.1607(4) 0.23248(19) 0.0439(12) Uani 1 1 d . . . H29A H 0.8047 0.2133 0.2095 0.066 Uiso 1 1 calc R . . H29B H 0.6942 0.1239 0.2165 0.066 Uiso 1 1 calc R . . H29C H 0.8205 0.1089 0.2393 0.066 Uiso 1 1 calc R . . C30 C 0.7554(4) 0.2151(6) 0.28131(19) 0.0566(16) Uani 1 1 d . . . H30A H 0.7071 0.2698 0.2751 0.068 Uiso 1 1 calc R . . H30B H 0.7182 0.1633 0.3046 0.068 Uiso 1 1 calc R . . C31 C 0.8879(4) 0.2833(4) 0.35328(16) 0.0322(10) Uani 1 1 d . . . C32 C 1.0592(4) 0.3365(3) 0.41697(16) 0.0288(9) Uani 1 1 d . . . C33 C 1.0254(3) 0.3397(3) 0.50731(16) 0.0284(9) Uani 1 1 d . . . C34 C 1.0970(4) 0.4323(4) 0.52863(18) 0.0379(11) Uani 1 1 d . . . H34 H 1.1251 0.4882 0.5076 0.045 Uiso 1 1 calc R . . C35 C 1.1267(4) 0.4416(4) 0.58108(18) 0.0401(11) Uani 1 1 d . . . H35 H 1.1752 0.5046 0.5960 0.048 Uiso 1 1 calc R . . C36 C 1.0861(4) 0.3598(4) 0.61190(17) 0.0416(12) Uani 1 1 d . . . H36 H 1.1085 0.3660 0.6476 0.050 Uiso 1 1 calc R . . C37 C 1.0133(4) 0.2697(4) 0.59049(17) 0.0383(11) Uani 1 1 d . . . H37 H 0.9842 0.2146 0.6118 0.046 Uiso 1 1 calc R . . C38 C 0.9820(3) 0.2583(4) 0.53827(16) 0.0303(9) Uani 1 1 d . . . C39 C 0.7960(4) 0.1593(4) 0.50119(16) 0.0311(9) Uani 1 1 d . . . C40 C 0.7755(3) -0.0270(4) 0.47153(17) 0.0327(10) Uani 1 1 d . . . C41 C 0.7219(5) -0.2021(5) 0.4351(3) 0.070(2) Uani 1 1 d D . . H41A H 0.7438 -0.2363 0.4669 0.083 Uiso 0.761(18) 1 calc PR A 1 H41B H 0.7889 -0.1913 0.4148 0.083 Uiso 0.761(18) 1 calc PR A 1 H41C H 0.6875 -0.2572 0.4576 0.083 Uiso 0.239(18) 1 calc PR A 2 H41D H 0.8070 -0.1963 0.4391 0.083 Uiso 0.239(18) 1 calc PR A 2 C42A C 0.6220(9) -0.2701(8) 0.4058(6) 0.101(6) Uani 0.761(18) 1 d PD A 1 H42A H 0.5547 -0.2764 0.4252 0.151 Uiso 0.761(18) 1 calc PR A 1 H42B H 0.6398 -0.3407 0.3995 0.151 Uiso 0.761(18) 1 calc PR A 1 H42C H 0.6049 -0.2385 0.3732 0.151 Uiso 0.761(18) 1 calc PR A 1 C42B C 0.674(3) -0.228(3) 0.3810(9) 0.101(6) Uani 0.239(18) 1 d PD A 2 H42D H 0.6845 -0.2999 0.3711 0.151 Uiso 0.239(18) 1 calc PR A 2 H42E H 0.7144 -0.1767 0.3590 0.151 Uiso 0.239(18) 1 calc PR A 2 H42F H 0.5912 -0.2257 0.3772 0.151 Uiso 0.239(18) 1 calc PR A 2 N100 N 0.2613(3) 0.7078(3) -0.02505(15) 0.0387(9) Uani 1 1 d . . . N101 N 0.8185(3) 0.6555(3) 0.08731(14) 0.0365(9) Uani 1 1 d . . . C100 C 0.2751(4) 0.6551(4) 0.01760(19) 0.0466(13) Uani 1 1 d . . . H100 H 0.2076 0.6254 0.0329 0.056 Uiso 1 1 calc R . . C101 C 0.3812(4) 0.6411(4) 0.04097(19) 0.0426(12) Uani 1 1 d . . . H101 H 0.3855 0.6018 0.0709 0.051 Uiso 1 1 calc R . . C102 C 0.3567(4) 0.7476(4) -0.04469(17) 0.0365(10) Uani 1 1 d . . . H102 H 0.3495 0.7838 -0.0755 0.044 Uiso 1 1 calc R . . C103 C 0.4675(4) 0.7409(4) -0.02384(17) 0.0359(10) Uani 1 1 d . . . H103 H 0.5332 0.7740 -0.0394 0.043 Uiso 1 1 calc R . . C104 C 0.4808(4) 0.6854(3) 0.01993(16) 0.0314(9) Uani 1 1 d . . . C105 C 0.5982(4) 0.6747(4) 0.04354(16) 0.0319(10) Uani 1 1 d . . . C106 C 0.6883(3) 0.7610(4) 0.04939(17) 0.0337(10) Uani 1 1 d . . . H106 H 0.6766 0.8285 0.0383 0.040 Uiso 1 1 calc R . . C107 C 0.7968(4) 0.7482(4) 0.07175(18) 0.0376(11) Uani 1 1 d . . . H107 H 0.8577 0.8086 0.0760 0.045 Uiso 1 1 calc R . . C108 C 0.6205(4) 0.5775(4) 0.06056(17) 0.0352(10) Uani 1 1 d . . . H108 H 0.5607 0.5162 0.0578 0.042 Uiso 1 1 calc R . . C109 C 0.7314(4) 0.5719(4) 0.08165(17) 0.0374(11) Uani 1 1 d . . . H109 H 0.7461 0.5052 0.0926 0.045 Uiso 1 1 calc R . . N200 N -0.0815(3) -0.0173(4) 0.31704(17) 0.0450(10) Uani 1 1 d . . . N201 N 0.4911(3) 0.0416(3) 0.43984(15) 0.0380(9) Uani 1 1 d . . . C200 C 0.0007(4) -0.0529(4) 0.2959(2) 0.0471(13) Uani 1 1 d . . . H200 H -0.0182 -0.0880 0.2631 0.057 Uiso 1 1 calc R . . C201 C 0.1151(4) -0.0423(4) 0.31863(18) 0.0390(11) Uani 1 1 d . . . H201 H 0.1715 -0.0692 0.3015 0.047 Uiso 1 1 calc R . . C202 C -0.0514(4) 0.0323(4) 0.3628(2) 0.0449(12) Uani 1 1 d . . . H202 H -0.1094 0.0591 0.3789 0.054 Uiso 1 1 calc R . . C203 C 0.0587(4) 0.0474(4) 0.38864(18) 0.0360(10) Uani 1 1 d . . . H203 H 0.0752 0.0842 0.4211 0.043 Uiso 1 1 calc R . . C204 C 0.1437(4) 0.0078(4) 0.36637(17) 0.0321(10) Uani 1 1 d . . . C205 C 0.2645(4) 0.0200(4) 0.39267(16) 0.0323(10) Uani 1 1 d . . . C206 C 0.3238(4) -0.0645(4) 0.39176(17) 0.0359(10) Uani 1 1 d . . . H206 H 0.2885 -0.1309 0.3751 0.043 Uiso 1 1 calc R . . C207 C 0.4360(4) -0.0488(4) 0.41589(17) 0.0382(11) Uani 1 1 d . . . H207 H 0.4760 -0.1066 0.4152 0.046 Uiso 1 1 calc R . . C208 C 0.3195(4) 0.1125(4) 0.41849(18) 0.0395(11) Uani 1 1 d . . . H208 H 0.2805 0.1707 0.4209 0.047 Uiso 1 1 calc R . . C209 C 0.4319(4) 0.1212(4) 0.44102(18) 0.0413(11) Uani 1 1 d . . . H209 H 0.4688 0.1867 0.4581 0.050 Uiso 1 1 calc R . . N300 N 0.3997(3) 0.5842(3) 0.33309(15) 0.0413(10) Uani 1 1 d . . . N301 N -0.1729(3) 0.5440(3) 0.21259(15) 0.0385(9) Uani 1 1 d . . . C300 C 0.3168(4) 0.6178(4) 0.35607(19) 0.0443(12) Uani 1 1 d . . . H300 H 0.3358 0.6476 0.3899 0.053 Uiso 1 1 calc R . . C301 C 0.2038(4) 0.6123(4) 0.33365(19) 0.0410(11) Uani 1 1 d . . . H301 H 0.1488 0.6392 0.3517 0.049 Uiso 1 1 calc R . . C302 C 0.3691(4) 0.5405(4) 0.28563(18) 0.0392(11) Uani 1 1 d . . . H302 H 0.4264 0.5154 0.2683 0.047 Uiso 1 1 calc R . . C303 C 0.2580(4) 0.5299(4) 0.26048(17) 0.0324(10) Uani 1 1 d . . . H303 H 0.2404 0.4976 0.2270 0.039 Uiso 1 1 calc R . . C304 C 0.1732(4) 0.5672(3) 0.28493(17) 0.0315(10) Uani 1 1 d . . . C305 C 0.0541(3) 0.5592(4) 0.25877(16) 0.0310(9) Uani 1 1 d . . . C306 C -0.0028(4) 0.4688(4) 0.23156(19) 0.0394(11) Uani 1 1 d . . . H306 H 0.0350 0.4100 0.2279 0.047 Uiso 1 1 calc R . . C307 C -0.1152(4) 0.4628(4) 0.2093(2) 0.0433(12) Uani 1 1 d . . . H307 H -0.1531 0.3989 0.1910 0.052 Uiso 1 1 calc R . . C308 C -0.0037(4) 0.6442(4) 0.26108(17) 0.0349(10) Uani 1 1 d . . . H308 H 0.0331 0.7092 0.2787 0.042 Uiso 1 1 calc R . . C309 C -0.1158(4) 0.6330(4) 0.23738(18) 0.0391(11) Uani 1 1 d . . . H309 H -0.1537 0.6921 0.2389 0.047 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 S1 0.0241(5) 0.0302(6) 0.0442(6) 0.0003(4) 0.0033(4) 0.0068(4) S2 0.0198(5) 0.0474(7) 0.0352(6) 0.0082(5) 0.0007(4) 0.0066(5) S3 0.0237(5) 0.0319(6) 0.0489(7) 0.0005(5) -0.0012(4) 0.0096(4) S4 0.0208(5) 0.0415(6) 0.0368(6) 0.0006(5) 0.0016(4) 0.0062(4) S5 0.0214(5) 0.0478(7) 0.0387(6) -0.0043(5) 0.0004(4) 0.0069(5) S6 0.0257(5) 0.0386(6) 0.0457(7) 0.0004(5) 0.0007(4) 0.0101(5) O1 0.0224(15) 0.0331(16) 0.0441(18) 0.0009(13) -0.0025(12) 0.0081(13) O2 0.0241(15) 0.0297(16) 0.055(2) -0.0073(14) -0.0072(13) 0.0050(13) O3 0.0229(15) 0.0472(19) 0.0338(16) -0.0005(14) 0.0023(12) -0.0015(13) O4 0.0205(14) 0.0485(19) 0.0359(17) 0.0092(14) -0.0026(12) 0.0013(13) O5 0.0200(15) 0.0328(16) 0.0464(18) 0.0043(13) -0.0017(12) 0.0072(12) O6 0.0202(14) 0.0289(16) 0.057(2) 0.0020(14) -0.0063(13) 0.0043(13) O7 0.0239(16) 0.078(3) 0.0363(18) -0.0041(17) 0.0010(13) 0.0099(16) O8 0.0263(15) 0.054(2) 0.0298(16) -0.0021(14) -0.0021(12) 0.0091(14) O9 0.0250(16) 0.079(3) 0.0376(18) -0.0065(17) 0.0024(14) 0.0067(17) O10 0.0243(16) 0.078(3) 0.0305(17) -0.0004(16) -0.0007(12) 0.0035(16) O11 0.0228(15) 0.0431(19) 0.0511(19) -0.0033(15) -0.0034(13) 0.0100(14) O12 0.0284(16) 0.0345(18) 0.069(2) -0.0123(16) -0.0124(15) 0.0088(14) N1 0.0187(16) 0.0285(18) 0.037(2) -0.0017(15) -0.0026(14) 0.0055(15) N2 0.0262(18) 0.0229(18) 0.0341(19) 0.0024(14) -0.0011(14) 0.0054(14) N3 0.0182(16) 0.0332(19) 0.0334(19) 0.0039(15) 0.0015(14) 0.0053(15) N4 0.0193(17) 0.043(2) 0.0285(19) 0.0063(16) 0.0013(14) 0.0034(16) N5 0.0193(16) 0.0300(19) 0.038(2) 0.0053(15) -0.0021(14) 0.0053(15) N6 0.0203(17) 0.0270(18) 0.0358(19) 0.0042(15) -0.0002(14) 0.0059(14) N7 0.0231(18) 0.048(2) 0.0299(19) 0.0041(17) 0.0023(14) 0.0085(16) N8 0.0214(17) 0.035(2) 0.0286(18) 0.0018(15) 0.0017(14) 0.0030(15) N9 0.0233(18) 0.044(2) 0.0298(19) 0.0007(16) 0.0012(14) 0.0069(16) N10 0.0192(17) 0.038(2) 0.0318(19) -0.0014(15) -0.0011(14) 0.0059(15) N11 0.0216(17) 0.033(2) 0.037(2) 0.0003(16) -0.0010(14) 0.0073(15) N12 0.0197(17) 0.037(2) 0.037(2) 0.0016(16) -0.0032(14) 0.0052(16) C1 0.052(3) 0.037(3) 0.056(3) 0.003(2) -0.007(2) 0.018(2) C2 0.030(2) 0.027(2) 0.058(3) -0.004(2) -0.006(2) 0.0080(19) C3 0.021(2) 0.033(2) 0.032(2) 0.0029(18) 0.0030(16) 0.0035(17) C4 0.022(2) 0.032(2) 0.031(2) 0.0037(17) 0.0019(16) 0.0045(17) C5 0.0178(19) 0.032(2) 0.033(2) -0.0025(17) 0.0005(16) 0.0029(17) C6 0.032(2) 0.048(3) 0.030(2) 0.006(2) 0.0036(18) 0.008(2) C7 0.033(2) 0.059(3) 0.030(2) -0.002(2) -0.0010(19) -0.001(2) C8 0.027(2) 0.043(3) 0.038(3) -0.010(2) -0.0007(18) 0.001(2) C9 0.025(2) 0.033(2) 0.039(2) -0.0011(19) 0.0044(18) 0.0035(18) C10 0.021(2) 0.031(2) 0.028(2) 0.0043(17) -0.0009(16) 0.0070(17) C11 0.026(2) 0.027(2) 0.033(2) 0.0042(17) 0.0026(17) 0.0062(17) C12 0.023(2) 0.027(2) 0.035(2) 0.0002(17) 0.0018(17) 0.0043(17) C13 0.018(2) 0.057(3) 0.036(2) -0.004(2) -0.0060(17) 0.002(2) C14 0.031(3) 0.122(6) 0.037(3) -0.001(3) -0.002(2) 0.007(3) C15 0.044(3) 0.035(3) 0.110(5) 0.003(3) -0.008(3) 0.000(2) C16 0.032(2) 0.030(2) 0.058(3) 0.002(2) -0.004(2) 0.010(2) C17 0.022(2) 0.034(2) 0.032(2) 0.0031(18) 0.0014(16) 0.0090(18) C18 0.022(2) 0.032(2) 0.026(2) 0.0024(16) 0.0008(16) 0.0039(17) C19 0.0191(19) 0.028(2) 0.034(2) 0.0019(17) 0.0015(16) 0.0084(17) C20 0.024(2) 0.045(3) 0.027(2) 0.0033(19) 0.0002(16) 0.0095(19) C21 0.028(2) 0.041(3) 0.031(2) -0.0062(19) -0.0064(18) 0.014(2) C22 0.018(2) 0.035(2) 0.044(3) -0.0090(19) -0.0061(17) 0.0059(18) C23 0.023(2) 0.035(2) 0.042(3) 0.0025(19) 0.0019(18) 0.0092(18) C24 0.0203(19) 0.030(2) 0.030(2) -0.0044(17) -0.0023(16) 0.0052(17) C25 0.026(2) 0.028(2) 0.030(2) 0.0048(17) 0.0022(16) 0.0094(17) C26 0.027(2) 0.046(3) 0.030(2) 0.0030(19) 0.0011(18) 0.013(2) C27 0.019(2) 0.070(4) 0.036(3) -0.005(2) -0.0027(18) 0.005(2) C28 0.041(3) 0.068(4) 0.048(3) -0.015(3) -0.009(2) 0.010(3) C29 0.043(3) 0.038(3) 0.049(3) -0.005(2) -0.013(2) 0.012(2) C30 0.022(2) 0.106(5) 0.035(3) -0.003(3) -0.006(2) 0.002(3) C31 0.024(2) 0.047(3) 0.027(2) 0.0022(19) 0.0026(17) 0.0103(19) C32 0.030(2) 0.027(2) 0.029(2) 0.0024(17) 0.0020(17) 0.0074(18) C33 0.0191(19) 0.034(2) 0.032(2) 0.0006(18) -0.0012(16) 0.0071(17) C34 0.031(2) 0.045(3) 0.038(3) -0.002(2) -0.0014(19) 0.011(2) C35 0.027(2) 0.048(3) 0.041(3) -0.015(2) -0.0050(19) 0.005(2) C36 0.037(3) 0.057(3) 0.028(2) -0.007(2) -0.0048(19) 0.008(2) C37 0.031(2) 0.052(3) 0.032(2) 0.003(2) 0.0030(18) 0.009(2) C38 0.022(2) 0.036(2) 0.032(2) -0.0027(18) -0.0020(16) 0.0069(18) C39 0.026(2) 0.039(2) 0.028(2) 0.0034(18) -0.0001(17) 0.0057(19) C40 0.022(2) 0.037(2) 0.038(2) 0.0040(19) 0.0013(17) 0.0038(19) C41 0.046(3) 0.041(3) 0.117(5) -0.027(3) -0.020(3) 0.016(3) C42A 0.048(6) 0.038(6) 0.199(13) -0.041(7) -0.050(7) 0.003(4) C42B 0.048(6) 0.038(6) 0.199(13) -0.041(7) -0.050(7) 0.003(4) N100 0.0268(19) 0.049(2) 0.039(2) -0.0006(18) -0.0001(16) 0.0049(18) N101 0.0288(19) 0.041(2) 0.040(2) -0.0005(17) 0.0007(16) 0.0092(17) C100 0.029(2) 0.060(3) 0.046(3) 0.009(2) -0.002(2) -0.002(2) C101 0.029(2) 0.057(3) 0.040(3) 0.009(2) -0.0001(19) 0.004(2) C102 0.037(3) 0.040(3) 0.034(2) 0.0038(19) 0.0000(19) 0.012(2) C103 0.028(2) 0.045(3) 0.038(2) 0.004(2) 0.0076(18) 0.012(2) C104 0.028(2) 0.032(2) 0.033(2) -0.0003(18) -0.0016(17) 0.0044(18) C105 0.027(2) 0.042(3) 0.028(2) -0.0035(18) 0.0008(17) 0.0093(19) C106 0.024(2) 0.034(2) 0.043(3) 0.0027(19) 0.0020(18) 0.0071(19) C107 0.030(2) 0.037(3) 0.045(3) 0.007(2) -0.0009(19) 0.008(2) C108 0.030(2) 0.034(2) 0.040(3) -0.0004(19) -0.0020(19) 0.0043(19) C109 0.035(2) 0.036(2) 0.042(3) 0.002(2) -0.003(2) 0.012(2) N200 0.029(2) 0.052(3) 0.053(3) 0.007(2) -0.0043(18) 0.0099(19) N201 0.0256(19) 0.047(2) 0.042(2) 0.0061(18) -0.0004(16) 0.0094(17) C200 0.042(3) 0.054(3) 0.044(3) -0.002(2) -0.009(2) 0.012(2) C201 0.032(2) 0.044(3) 0.043(3) 0.007(2) 0.003(2) 0.011(2) C202 0.033(3) 0.052(3) 0.054(3) 0.011(2) 0.002(2) 0.018(2) C203 0.032(2) 0.034(2) 0.043(3) 0.005(2) 0.0001(19) 0.0092(19) C204 0.025(2) 0.036(2) 0.036(2) 0.0095(19) 0.0013(17) 0.0087(19) C205 0.025(2) 0.039(2) 0.034(2) 0.0084(19) 0.0018(17) 0.0058(19) C206 0.030(2) 0.041(3) 0.039(2) 0.002(2) -0.0019(18) 0.014(2) C207 0.033(2) 0.044(3) 0.039(3) 0.002(2) -0.0006(19) 0.014(2) C208 0.030(2) 0.040(3) 0.049(3) 0.008(2) -0.001(2) 0.012(2) C209 0.036(3) 0.044(3) 0.042(3) 0.003(2) -0.002(2) 0.006(2) N300 0.032(2) 0.047(2) 0.045(2) 0.0011(19) -0.0025(17) 0.0098(18) N301 0.0249(19) 0.043(2) 0.050(2) 0.0126(18) -0.0002(16) 0.0127(17) C300 0.037(3) 0.054(3) 0.039(3) 0.000(2) -0.008(2) 0.007(2) C301 0.028(2) 0.052(3) 0.045(3) 0.002(2) 0.002(2) 0.012(2) C302 0.030(2) 0.046(3) 0.043(3) 0.006(2) 0.0028(19) 0.011(2) C303 0.026(2) 0.034(2) 0.038(2) 0.0052(19) 0.0034(18) 0.0097(18) C304 0.025(2) 0.032(2) 0.038(2) 0.0086(19) 0.0024(17) 0.0057(18) C305 0.025(2) 0.033(2) 0.036(2) 0.0086(18) 0.0036(17) 0.0054(18) C306 0.025(2) 0.033(2) 0.060(3) 0.006(2) -0.001(2) 0.0071(19) C307 0.030(2) 0.038(3) 0.060(3) 0.002(2) -0.006(2) 0.005(2) C308 0.033(2) 0.035(2) 0.039(2) 0.0017(19) -0.0013(19) 0.015(2) C309 0.030(2) 0.046(3) 0.045(3) 0.006(2) 0.001(2) 0.015(2) _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 S1 C4 1.674(4) . ? S2 C11 1.666(4) . ? S3 C18 1.666(4) . ? S4 C25 1.673(4) . ? S5 C32 1.670(4) . ? S6 C39 1.675(4) . ? O1 C3 1.217(5) . ? O2 C3 1.338(5) . ? O2 C2 1.459(5) . ? O3 C12 1.202(5) . ? O4 C12 1.332(5) . ? O4 C13 1.449(5) . ? O5 C17 1.216(5) . ? O6 C17 1.332(5) . ? O6 C16 1.450(5) . ? O7 C26 1.204(5) . ? O8 C26 1.325(5) . ? O8 C27 1.462(5) . ? O9 C31 1.216(5) . ? O10 C31 1.325(5) . ? O10 C30 1.464(5) . ? O11 C40 1.216(5) . ? O12 C40 1.338(5) . ? O12 C41 1.450(6) . ? N1 C3 1.372(5) . ? N1 C4 1.379(5) . ? N1 H1N 0.895(19) . ? N2 C4 1.341(5) . ? N2 C5 1.429(5) . ? N2 H2N 0.894(19) . ? N3 C11 1.330(5) . ? N3 C10 1.421(5) . ? N3 H3N 0.904(19) . ? N4 C12 1.377(5) . ? N4 C11 1.395(5) . ? N4 H4N 0.911(19) . ? N5 C18 1.370(5) . ? N5 C17 1.375(5) . ? N5 H5N 0.907(19) . ? N6 C18 1.345(5) . ? N6 C19 1.426(5) . ? N6 H6N 0.890(19) . ? N7 C26 1.380(5) . ? N7 C25 1.389(5) . ? N7 H7N 0.911(19) . ? N8 C25 1.336(5) . ? N8 C24 1.418(5) . ? N8 H8N 0.888(19) . ? N9 C31 1.374(5) . ? N9 C32 1.390(5) . ? N9 H9N 0.904(19) . ? N10 C32 1.339(6) . ? N10 C33 1.416(5) . ? N10 H10N 0.894(19) . ? N11 C39 1.340(5) . ? N11 C38 1.425(5) . ? N11 H11N 0.901(19) . ? N12 C40 1.369(6) . ? N12 C39 1.372(6) . ? N12 H12N 0.914(19) . ? C1 C2 1.485(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.387(6) . ? C5 C10 1.398(6) . ? C6 C7 1.390(7) . ? C6 H6 0.9500 . ? C7 C8 1.381(7) . ? C7 H7 0.9500 . ? C8 C9 1.369(6) . ? C8 H8 0.9500 . ? C9 C10 1.390(6) . ? C9 H9 0.9500 . ? C13 C14 1.482(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.479(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C19 C20 1.387(6) . ? C19 C24 1.404(6) . ? C20 C21 1.379(6) . ? C20 H20 0.9500 . ? C21 C22 1.388(7) . ? C21 H21 0.9500 . ? C22 C23 1.386(6) . ? C22 H22 0.9500 . ? C23 C24 1.382(6) . ? C23 H23 0.9500 . ? C27 C28 1.490(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.486(7) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C33 C34 1.392(6) . ? C33 C38 1.395(6) . ? C34 C35 1.388(6) . ? C34 H34 0.9500 . ? C35 C36 1.388(7) . ? C35 H35 0.9500 . ? C36 C37 1.375(7) . ? C36 H36 0.9500 . ? C37 C38 1.386(6) . ? C37 H37 0.9500 . ? C41 C42A 1.467(9) . ? C41 C42B 1.487(19) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C41 H41C 0.9900 . ? C41 H41D 0.9900 . ? C42A H42A 0.9800 . ? C42A H42B 0.9800 . ? C42A H42C 0.9800 . ? C42B H42D 0.9800 . ? C42B H42E 0.9800 . ? C42B H42F 0.9800 . ? N100 C102 1.310(6) . ? N100 C100 1.339(6) . ? N101 C107 1.328(6) . ? N101 C109 1.336(6) . ? C100 C101 1.386(6) . ? C100 H100 0.9500 . ? C101 C104 1.383(6) . ? C101 H101 0.9500 . ? C102 C103 1.387(6) . ? C102 H102 0.9500 . ? C103 C104 1.383(6) . ? C103 H103 0.9500 . ? C104 C105 1.496(5) . ? C105 C106 1.379(6) . ? C105 C108 1.396(6) . ? C106 C107 1.397(6) . ? C106 H106 0.9500 . ? C107 H107 0.9500 . ? C108 C109 1.387(6) . ? C108 H108 0.9500 . ? C109 H109 0.9500 . ? N200 C200 1.311(7) . ? N200 C202 1.333(7) . ? N201 C207 1.328(6) . ? N201 C209 1.341(6) . ? C200 C201 1.404(6) . ? C200 H200 0.9500 . ? C201 C204 1.379(7) . ? C201 H201 0.9500 . ? C202 C203 1.385(6) . ? C202 H202 0.9500 . ? C203 C204 1.378(6) . ? C203 H203 0.9500 . ? C204 C205 1.503(6) . ? C205 C208 1.369(7) . ? C205 C206 1.395(6) . ? C206 C207 1.390(6) . ? C206 H206 0.9500 . ? C207 H207 0.9500 . ? C208 C209 1.384(6) . ? C208 H208 0.9500 . ? C209 H209 0.9500 . ? N300 C300 1.331(7) . ? N300 C302 1.344(6) . ? N301 C309 1.331(6) . ? N301 C307 1.351(6) . ? C300 C301 1.395(6) . ? C300 H300 0.9500 . ? C301 C304 1.380(7) . ? C301 H301 0.9500 . ? C302 C303 1.393(6) . ? C302 H302 0.9500 . ? C303 C304 1.392(6) . ? C303 H303 0.9500 . ? C304 C305 1.489(5) . ? C305 C306 1.371(6) . ? C305 C308 1.392(6) . ? C306 C307 1.386(6) . ? C306 H306 0.9500 . ? C307 H307 0.9500 . ? C308 C309 1.388(6) . ? C308 H308 0.9500 . ? C309 H309 0.9500 . ? 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 C3 O2 C2 117.4(3) . . ? C12 O4 C13 117.1(3) . . ? C17 O6 C16 116.1(3) . . ? C26 O8 C27 116.3(3) . . ? C31 O10 C30 116.5(4) . . ? C40 O12 C41 115.9(3) . . ? C3 N1 C4 126.9(3) . . ? C3 N1 H1N 116(3) . . ? C4 N1 H1N 117(3) . . ? C4 N2 C5 122.3(3) . . ? C4 N2 H2N 118(3) . . ? C5 N2 H2N 118(3) . . ? C11 N3 C10 125.6(3) . . ? C11 N3 H3N 117(3) . . ? C10 N3 H3N 116(3) . . ? C12 N4 C11 128.2(4) . . ? C12 N4 H4N 113(3) . . ? C11 N4 H4N 118(3) . . ? C18 N5 C17 126.8(3) . . ? C18 N5 H5N 117(3) . . ? C17 N5 H5N 115(3) . . ? C18 N6 C19 121.6(3) . . ? C18 N6 H6N 117(3) . . ? C19 N6 H6N 122(3) . . ? C26 N7 C25 127.3(4) . . ? C26 N7 H7N 117(3) . . ? C25 N7 H7N 114(3) . . ? C25 N8 C24 124.8(3) . . ? C25 N8 H8N 114(3) . . ? C24 N8 H8N 120(3) . . ? C31 N9 C32 127.4(4) . . ? C31 N9 H9N 115(3) . . ? C32 N9 H9N 114(3) . . ? C32 N10 C33 125.7(3) . . ? C32 N10 H10N 125(3) . . ? C33 N10 H10N 109(3) . . ? C39 N11 C38 122.4(4) . . ? C39 N11 H11N 117(3) . . ? C38 N11 H11N 120(3) . . ? C40 N12 C39 126.8(3) . . ? C40 N12 H12N 116(3) . . ? C39 N12 H12N 117(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 111.4(4) . . ? O2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? O2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? O1 C3 O2 124.8(4) . . ? O1 C3 N1 126.6(4) . . ? O2 C3 N1 108.6(3) . . ? N2 C4 N1 117.5(4) . . ? N2 C4 S1 123.5(3) . . ? N1 C4 S1 118.9(3) . . ? C6 C5 C10 119.7(4) . . ? C6 C5 N2 120.1(4) . . ? C10 C5 N2 120.2(4) . . ? C5 C6 C7 120.0(4) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.3(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.4(4) . . ? C9 C10 N3 121.4(4) . . ? C5 C10 N3 119.1(4) . . ? N3 C11 N4 115.8(3) . . ? N3 C11 S2 126.9(3) . . ? N4 C11 S2 117.3(3) . . ? O3 C12 O4 126.0(4) . . ? O3 C12 N4 126.5(4) . . ? O4 C12 N4 107.4(4) . . ? O4 C13 C14 106.4(4) . . ? O4 C13 H13A 110.5 . . ? C14 C13 H13A 110.5 . . ? O4 C13 H13B 110.5 . . ? C14 C13 H13B 110.5 . . ? H13A C13 H13B 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 C15 107.1(4) . . ? O6 C16 H16A 110.3 . . ? C15 C16 H16A 110.3 . . ? O6 C16 H16B 110.3 . . ? C15 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? O5 C17 O6 125.0(4) . . ? O5 C17 N5 126.0(4) . . ? O6 C17 N5 109.0(3) . . ? N6 C18 N5 117.2(4) . . ? N6 C18 S3 123.5(3) . . ? N5 C18 S3 119.4(3) . . ? C20 C19 C24 119.3(4) . . ? C20 C19 N6 120.0(4) . . ? C24 C19 N6 120.7(4) . . ? C21 C20 C19 120.4(4) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.2(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.9(4) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 120.2(4) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C19 119.9(4) . . ? C23 C24 N8 121.3(4) . . ? C19 C24 N8 118.8(4) . . ? N8 C25 N7 116.1(3) . . ? N8 C25 S4 125.9(3) . . ? N7 C25 S4 118.0(3) . . ? O7 C26 O8 125.8(4) . . ? O7 C26 N7 126.0(4) . . ? O8 C26 N7 108.2(4) . . ? O8 C27 C28 105.3(4) . . ? O8 C27 H27A 110.7 . . ? C28 C27 H27A 110.7 . . ? O8 C27 H27B 110.7 . . ? C28 C27 H27B 110.7 . . ? H27A C27 H27B 108.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O10 C30 C29 105.6(4) . . ? O10 C30 H30A 110.6 . . ? C29 C30 H30A 110.6 . . ? O10 C30 H30B 110.6 . . ? C29 C30 H30B 110.6 . . ? H30A C30 H30B 108.7 . . ? O9 C31 O10 125.7(4) . . ? O9 C31 N9 125.7(4) . . ? O10 C31 N9 108.5(4) . . ? N10 C32 N9 115.5(4) . . ? N10 C32 S5 126.2(3) . . ? N9 C32 S5 118.3(3) . . ? C34 C33 C38 120.5(4) . . ? C34 C33 N10 121.3(4) . . ? C38 C33 N10 118.1(4) . . ? C35 C34 C33 119.1(5) . . ? C35 C34 H34 120.5 . . ? C33 C34 H34 120.5 . . ? C36 C35 C34 120.6(4) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C37 C36 C35 119.7(4) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C38 120.9(5) . . ? C36 C37 H37 119.5 . . ? C38 C37 H37 119.5 . . ? C37 C38 C33 119.1(4) . . ? C37 C38 N11 120.7(4) . . ? C33 C38 N11 120.2(4) . . ? N11 C39 N12 117.3(4) . . ? N11 C39 S6 123.1(3) . . ? N12 C39 S6 119.6(3) . . ? O11 C40 O12 124.3(4) . . ? O11 C40 N12 126.4(4) . . ? O12 C40 N12 109.3(3) . . ? O12 C41 C42A 108.6(5) . . ? O12 C41 C42B 104.9(13) . . ? C42A C41 C42B 40.9(14) . . ? O12 C41 H41A 110.0 . . ? C42A C41 H41A 110.0 . . ? C42B C41 H41A 141.3 . . ? O12 C41 H41B 110.0 . . ? C42A C41 H41B 110.0 . . ? C42B C41 H41B 73.7 . . ? H41A C41 H41B 108.4 . . ? O12 C41 H41C 110.8 . . ? C42A C41 H41C 71.7 . . ? C42B C41 H41C 110.8 . . ? H41A C41 H41C 40.6 . . ? H41B C41 H41C 135.9 . . ? O12 C41 H41D 110.8 . . ? C42A C41 H41D 137.0 . . ? C42B C41 H41D 110.8 . . ? H41A C41 H41D 71.8 . . ? H41B C41 H41D 39.1 . . ? H41C C41 H41D 108.8 . . ? C41 C42A H42A 109.5 . . ? C41 C42A H42B 109.5 . . ? C41 C42A H42C 109.5 . . ? C41 C42B H42D 109.5 . . ? C41 C42B H42E 109.5 . . ? H42D C42B H42E 109.5 . . ? C41 C42B H42F 109.5 . . ? H42D C42B H42F 109.5 . . ? H42E C42B H42F 109.5 . . ? C102 N100 C100 115.6(4) . . ? C107 N101 C109 117.7(4) . . ? N100 C100 C101 124.4(5) . . ? N100 C100 H100 117.8 . . ? C101 C100 H100 117.8 . . ? C104 C101 C100 118.9(5) . . ? C104 C101 H101 120.6 . . ? C100 C101 H101 120.6 . . ? N100 C102 C103 124.9(4) . . ? N100 C102 H102 117.6 . . ? C103 C102 H102 117.6 . . ? C104 C103 C102 119.0(4) . . ? C104 C103 H103 120.5 . . ? C102 C103 H103 120.5 . . ? C103 C104 C101 117.2(4) . . ? C103 C104 C105 121.1(4) . . ? C101 C104 C105 121.7(4) . . ? C106 C105 C108 117.7(4) . . ? C106 C105 C104 120.9(4) . . ? C108 C105 C104 121.3(4) . . ? C105 C106 C107 119.4(4) . . ? C105 C106 H106 120.3 . . ? C107 C106 H106 120.3 . . ? N101 C107 C106 122.9(4) . . ? N101 C107 H107 118.5 . . ? C106 C107 H107 118.5 . . ? C109 C108 C105 118.9(4) . . ? C109 C108 H108 120.5 . . ? C105 C108 H108 120.5 . . ? N101 C109 C108 123.3(4) . . ? N101 C109 H109 118.3 . . ? C108 C109 H109 118.3 . . ? C200 N200 C202 116.2(4) . . ? C207 N201 C209 116.5(4) . . ? N200 C200 C201 124.2(5) . . ? N200 C200 H200 117.9 . . ? C201 C200 H200 117.9 . . ? C204 C201 C200 118.6(5) . . ? C204 C201 H201 120.7 . . ? C200 C201 H201 120.7 . . ? N200 C202 C203 124.4(5) . . ? N200 C202 H202 117.8 . . ? C203 C202 H202 117.8 . . ? C204 C203 C202 118.7(5) . . ? C204 C203 H203 120.6 . . ? C202 C203 H203 120.6 . . ? C203 C204 C201 117.9(4) . . ? C203 C204 C205 121.4(4) . . ? C201 C204 C205 120.7(4) . . ? C208 C205 C206 117.8(4) . . ? C208 C205 C204 121.9(4) . . ? C206 C205 C204 120.2(4) . . ? C207 C206 C205 118.1(4) . . ? C207 C206 H206 121.0 . . ? C205 C206 H206 121.0 . . ? N201 C207 C206 124.4(4) . . ? N201 C207 H207 117.8 . . ? C206 C207 H207 117.8 . . ? C205 C208 C209 120.0(4) . . ? C205 C208 H208 120.0 . . ? C209 C208 H208 120.0 . . ? N201 C209 C208 123.1(5) . . ? N201 C209 H209 118.5 . . ? C208 C209 H209 118.5 . . ? C300 N300 C302 116.3(4) . . ? C309 N301 C307 116.9(4) . . ? N300 C300 C301 124.2(5) . . ? N300 C300 H300 117.9 . . ? C301 C300 H300 117.9 . . ? C304 C301 C300 119.1(5) . . ? C304 C301 H301 120.5 . . ? C300 C301 H301 120.5 . . ? N300 C302 C303 123.6(4) . . ? N300 C302 H302 118.2 . . ? C303 C302 H302 118.2 . . ? C304 C303 C302 119.2(4) . . ? C304 C303 H303 120.4 . . ? C302 C303 H303 120.4 . . ? C301 C304 C303 117.7(4) . . ? C301 C304 C305 121.7(4) . . ? C303 C304 C305 120.6(4) . . ? C306 C305 C308 117.4(4) . . ? C306 C305 C304 121.8(4) . . ? C308 C305 C304 120.8(4) . . ? C305 C306 C307 120.2(4) . . ? C305 C306 H306 119.9 . . ? C307 C306 H306 119.9 . . ? N301 C307 C306 122.6(5) . . ? N301 C307 H307 118.7 . . ? C306 C307 H307 118.7 . . ? C309 C308 C305 119.2(4) . . ? C309 C308 H308 120.4 . . ? C305 C308 H308 120.4 . . ? N301 C309 C308 123.6(4) . . ? N301 C309 H309 118.2 . . ? C308 C309 H309 118.2 . . ? 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 C3 O2 C2 C1 -89.0(5) . . . . ? C2 O2 C3 O1 -1.3(6) . . . . ? C2 O2 C3 N1 177.6(4) . . . . ? C4 N1 C3 O1 -1.7(7) . . . . ? C4 N1 C3 O2 179.4(4) . . . . ? C5 N2 C4 N1 -176.7(4) . . . . ? C5 N2 C4 S1 3.5(6) . . . . ? C3 N1 C4 N2 4.1(6) . . . . ? C3 N1 C4 S1 -176.1(3) . . . . ? C4 N2 C5 C6 102.0(5) . . . . ? C4 N2 C5 C10 -79.2(5) . . . . ? C10 C5 C6 C7 0.9(6) . . . . ? N2 C5 C6 C7 179.7(4) . . . . ? C5 C6 C7 C8 1.2(7) . . . . ? C6 C7 C8 C9 -1.7(7) . . . . ? C7 C8 C9 C10 0.1(7) . . . . ? C8 C9 C10 C5 2.0(6) . . . . ? C8 C9 C10 N3 177.9(4) . . . . ? C6 C5 C10 C9 -2.5(6) . . . . ? N2 C5 C10 C9 178.7(4) . . . . ? C6 C5 C10 N3 -178.4(4) . . . . ? N2 C5 C10 N3 2.8(6) . . . . ? C11 N3 C10 C9 47.1(6) . . . . ? C11 N3 C10 C5 -137.1(4) . . . . ? C10 N3 C11 N4 -172.6(4) . . . . ? C10 N3 C11 S2 8.9(6) . . . . ? C12 N4 C11 N3 -2.6(6) . . . . ? C12 N4 C11 S2 176.1(3) . . . . ? C13 O4 C12 O3 -9.1(6) . . . . ? C13 O4 C12 N4 172.3(4) . . . . ? C11 N4 C12 O3 -0.5(7) . . . . ? C11 N4 C12 O4 178.1(4) . . . . ? C12 O4 C13 C14 -155.1(5) . . . . ? C17 O6 C16 C15 179.3(5) . . . . ? C16 O6 C17 O5 -4.1(6) . . . . ? C16 O6 C17 N5 175.5(4) . . . . ? C18 N5 C17 O5 3.9(7) . . . . ? C18 N5 C17 O6 -175.8(4) . . . . ? C19 N6 C18 N5 177.6(4) . . . . ? C19 N6 C18 S3 -2.6(6) . . . . ? C17 N5 C18 N6 -6.8(6) . . . . ? C17 N5 C18 S3 173.5(3) . . . . ? C18 N6 C19 C20 -102.6(5) . . . . ? C18 N6 C19 C24 78.1(5) . . . . ? C24 C19 C20 C21 -0.9(6) . . . . ? N6 C19 C20 C21 179.8(4) . . . . ? C19 C20 C21 C22 -0.8(6) . . . . ? C20 C21 C22 C23 2.1(6) . . . . ? C21 C22 C23 C24 -1.6(6) . . . . ? C22 C23 C24 C19 -0.2(6) . . . . ? C22 C23 C24 N8 -177.0(4) . . . . ? C20 C19 C24 C23 1.5(6) . . . . ? N6 C19 C24 C23 -179.3(3) . . . . ? C20 C19 C24 N8 178.3(3) . . . . ? N6 C19 C24 N8 -2.4(6) . . . . ? C25 N8 C24 C23 -57.1(6) . . . . ? C25 N8 C24 C19 126.0(4) . . . . ? C24 N8 C25 N7 -179.6(4) . . . . ? C24 N8 C25 S4 -0.4(6) . . . . ? C26 N7 C25 N8 4.6(6) . . . . ? C26 N7 C25 S4 -174.6(4) . . . . ? C27 O8 C26 O7 6.3(7) . . . . ? C27 O8 C26 N7 -173.4(4) . . . . ? C25 N7 C26 O7 -5.9(8) . . . . ? C25 N7 C26 O8 173.7(4) . . . . ? C26 O8 C27 C28 165.1(4) . . . . ? C31 O10 C30 C29 -156.2(4) . . . . ? C30 O10 C31 O9 -4.2(7) . . . . ? C30 O10 C31 N9 174.1(4) . . . . ? C32 N9 C31 O9 6.4(8) . . . . ? C32 N9 C31 O10 -171.9(4) . . . . ? C33 N10 C32 N9 178.6(4) . . . . ? C33 N10 C32 S5 -1.4(6) . . . . ? C31 N9 C32 N10 -7.4(6) . . . . ? C31 N9 C32 S5 172.5(4) . . . . ? C32 N10 C33 C34 56.5(6) . . . . ? C32 N10 C33 C38 -127.1(4) . . . . ? C38 C33 C34 C35 1.4(6) . . . . ? N10 C33 C34 C35 177.7(4) . . . . ? C33 C34 C35 C36 0.3(7) . . . . ? C34 C35 C36 C37 -1.7(7) . . . . ? C35 C36 C37 C38 1.6(7) . . . . ? C36 C37 C38 C33 0.1(7) . . . . ? C36 C37 C38 N11 178.6(4) . . . . ? C34 C33 C38 C37 -1.5(6) . . . . ? N10 C33 C38 C37 -178.0(4) . . . . ? C34 C33 C38 N11 179.9(4) . . . . ? N10 C33 C38 N11 3.4(6) . . . . ? C39 N11 C38 C37 102.8(5) . . . . ? C39 N11 C38 C33 -78.7(5) . . . . ? C38 N11 C39 N12 178.4(4) . . . . ? C38 N11 C39 S6 -0.7(6) . . . . ? C40 N12 C39 N11 1.0(7) . . . . ? C40 N12 C39 S6 -179.9(4) . . . . ? C41 O12 C40 O11 0.2(7) . . . . ? C41 O12 C40 N12 178.4(5) . . . . ? C39 N12 C40 O11 0.6(8) . . . . ? C39 N12 C40 O12 -177.6(4) . . . . ? C40 O12 C41 C42A -176.1(9) . . . . ? C40 O12 C41 C42B -133.5(18) . . . . ? C102 N100 C100 C101 -0.1(8) . . . . ? N100 C100 C101 C104 1.1(8) . . . . ? C100 N100 C102 C103 -1.7(7) . . . . ? N100 C102 C103 C104 2.4(7) . . . . ? C102 C103 C104 C101 -1.2(7) . . . . ? C102 C103 C104 C105 179.2(4) . . . . ? C100 C101 C104 C103 -0.4(7) . . . . ? C100 C101 C104 C105 179.2(5) . . . . ? C103 C104 C105 C106 44.7(6) . . . . ? C101 C104 C105 C106 -134.8(5) . . . . ? C103 C104 C105 C108 -135.6(5) . . . . ? C101 C104 C105 C108 44.9(7) . . . . ? C108 C105 C106 C107 0.0(7) . . . . ? C104 C105 C106 C107 179.8(4) . . . . ? C109 N101 C107 C106 -0.9(7) . . . . ? C105 C106 C107 N101 0.9(7) . . . . ? C106 C105 C108 C109 -1.0(7) . . . . ? C104 C105 C108 C109 179.3(4) . . . . ? C107 N101 C109 C108 -0.1(7) . . . . ? C105 C108 C109 N101 1.0(7) . . . . ? C202 N200 C200 C201 0.5(8) . . . . ? N200 C200 C201 C204 0.5(8) . . . . ? C200 N200 C202 C203 -0.4(8) . . . . ? N200 C202 C203 C204 -0.8(8) . . . . ? C202 C203 C204 C201 1.8(7) . . . . ? C202 C203 C204 C205 -179.1(4) . . . . ? C200 C201 C204 C203 -1.6(7) . . . . ? C200 C201 C204 C205 179.2(4) . . . . ? C203 C204 C205 C208 -41.3(7) . . . . ? C201 C204 C205 C208 137.8(5) . . . . ? C203 C204 C205 C206 138.0(5) . . . . ? C201 C204 C205 C206 -42.9(6) . . . . ? C208 C205 C206 C207 -1.7(7) . . . . ? C204 C205 C206 C207 178.9(4) . . . . ? C209 N201 C207 C206 1.2(7) . . . . ? C205 C206 C207 N201 0.0(7) . . . . ? C206 C205 C208 C209 2.4(7) . . . . ? C204 C205 C208 C209 -178.3(4) . . . . ? C207 N201 C209 C208 -0.5(7) . . . . ? C205 C208 C209 N201 -1.3(8) . . . . ? C302 N300 C300 C301 -1.4(8) . . . . ? N300 C300 C301 C304 1.5(8) . . . . ? C300 N300 C302 C303 0.2(7) . . . . ? N300 C302 C303 C304 0.8(7) . . . . ? C300 C301 C304 C303 -0.4(7) . . . . ? C300 C301 C304 C305 -179.8(4) . . . . ? C302 C303 C304 C301 -0.6(7) . . . . ? C302 C303 C304 C305 178.8(4) . . . . ? C301 C304 C305 C306 -136.8(5) . . . . ? C303 C304 C305 C306 43.8(6) . . . . ? C301 C304 C305 C308 43.3(7) . . . . ? C303 C304 C305 C308 -136.1(5) . . . . ? C308 C305 C306 C307 -2.5(7) . . . . ? C304 C305 C306 C307 177.6(5) . . . . ? C309 N301 C307 C306 1.8(8) . . . . ? C305 C306 C307 N301 0.8(8) . . . . ? C306 C305 C308 C309 1.8(7) . . . . ? C304 C305 C308 C309 -178.3(4) . . . . ? C307 N301 C309 C308 -2.5(7) . . . . ? C305 C308 C309 N301 0.8(8) . . . . ? 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 N1 H1N N101 0.895(19) 2.03(2) 2.909(5) 169(4) 1_455 N2 H2N O1 0.894(19) 2.01(4) 2.703(4) 133(4) . N2 H2N O5 0.894(19) 2.43(3) 3.143(4) 137(4) . N3 H3N O3 0.904(19) 2.00(3) 2.719(4) 135(4) . N3 H3N S1 0.904(19) 2.81(4) 3.452(4) 129(4) . N4 H4N S2 0.911(19) 2.51(2) 3.405(4) 167(4) 2_675 N5 H5N N301 0.907(19) 1.98(2) 2.885(5) 174(4) 1_655 N6 H6N O5 0.890(19) 1.96(3) 2.676(5) 136(4) . N6 H6N O1 0.890(19) 2.61(3) 3.322(4) 138(4) . N7 H7N S5 0.911(19) 2.55(2) 3.426(4) 163(4) 1_455 N8 H8N O7 0.888(19) 1.94(3) 2.684(4) 140(4) . N8 H8N S3 0.888(19) 2.85(4) 3.432(4) 124(4) . N9 H9N S4 0.904(19) 2.53(3) 3.387(4) 159(4) 1_655 N10 H10N O9 0.894(19) 2.05(4) 2.669(4) 126(4) . N10 H10N S6 0.894(19) 2.76(3) 3.467(4) 137(4) . N11 H11N O11 0.901(19) 1.97(4) 2.679(5) 135(4) . N11 H11N O11 0.901(19) 2.52(3) 3.258(4) 140(4) 2_756 N12 H12N N201 0.914(19) 2.02(2) 2.918(5) 167(4) . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 67.08 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.698 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.162 data_TM-44bpe _database_code_depnum_ccdc_archive 'CCDC 831127' #TrackingRef '- bp_bpe_co-crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H14 N4 O4 S2), C12 H12 N2' _chemical_formula_sum 'C36 H40 N10 O8 S4' _chemical_formula_weight 869.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0972(2) _cell_length_b 9.5762(2) _cell_length_c 23.8891(3) _cell_angle_alpha 86.2240(10) _cell_angle_beta 88.2730(10) _cell_angle_gamma 88.2140(10) _cell_volume 2074.79(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 2.632 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6211 _exptl_absorpt_correction_T_max 0.8581 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10604 _diffrn_reflns_av_R_equivalents 0.1069 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 66.84 _reflns_number_total 7144 _reflns_number_gt 5384 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0808P)^2^+1.5371P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7144 _refine_ls_number_parameters 551 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 S1 S 0.35892(12) -0.01462(9) 0.34917(5) 0.0448(3) Uani 1 1 d . . . S2 S -0.26125(11) 0.30570(9) 0.35597(4) 0.0359(2) Uani 1 1 d . . . S3 S -0.04832(11) 0.16910(11) 0.13855(5) 0.0452(3) Uani 1 1 d . . . S4 S 0.23989(11) 0.74252(11) 0.15153(4) 0.0413(3) Uani 1 1 d . . . O1 O 0.1701(3) 0.4270(2) 0.30868(12) 0.0412(6) Uani 1 1 d . . . O2 O 0.4075(3) 0.4813(2) 0.31739(11) 0.0363(6) Uani 1 1 d . . . O3 O -0.0350(3) 0.1396(2) 0.51708(10) 0.0399(7) Uani 1 1 d . . . O4 O -0.1097(3) 0.3526(2) 0.54376(10) 0.0369(6) Uani 1 1 d . . . O5 O 0.3823(3) 0.3197(3) 0.20403(11) 0.0426(7) Uani 1 1 d . . . O6 O 0.4531(3) 0.0969(3) 0.18867(12) 0.0462(7) Uani 1 1 d . . . O7 O 0.1498(3) 0.5436(3) -0.01327(10) 0.0371(6) Uani 1 1 d . . . O8 O 0.3739(3) 0.6283(3) -0.03572(10) 0.0333(6) Uani 1 1 d . . . N1 N 0.3468(4) 0.2598(3) 0.33429(13) 0.0322(7) Uani 1 1 d . . . H1N H 0.435(5) 0.263(4) 0.3414(18) 0.039 Uiso 1 1 d . . . N2 N 0.1251(3) 0.1523(3) 0.32685(13) 0.0327(7) Uani 1 1 d . . . H2N H 0.091(5) 0.230(4) 0.3206(17) 0.039 Uiso 1 1 d . . . N3 N -0.0998(3) 0.1052(3) 0.40938(12) 0.0286(6) Uani 1 1 d . . . H3N H -0.059(4) 0.066(4) 0.4416(17) 0.034 Uiso 1 1 d . . . N4 N -0.1645(3) 0.2980(3) 0.45913(12) 0.0298(6) Uani 1 1 d . . . H4N H -0.209(4) 0.391(4) 0.4577(16) 0.036 Uiso 1 1 d . . . N5 N 0.2284(3) 0.1678(4) 0.16639(13) 0.0362(7) Uani 1 1 d . . . H5N H 0.212(5) 0.086(5) 0.1575(18) 0.043 Uiso 1 1 d . . . N6 N 0.1001(3) 0.3784(3) 0.17635(13) 0.0337(7) Uani 1 1 d . . . H6N H 0.184(5) 0.412(4) 0.1864(17) 0.040 Uiso 1 1 d . . . N7 N 0.0617(3) 0.5973(3) 0.09221(12) 0.0295(6) Uani 1 1 d . . . H7N H 0.034(4) 0.560(4) 0.0611(17) 0.035 Uiso 1 1 d . . . N8 N 0.2811(3) 0.6640(3) 0.04831(12) 0.0300(6) Uani 1 1 d . . . H8N H 0.358(5) 0.710(4) 0.0503(16) 0.036 Uiso 1 1 d . . . C1 C 0.3717(5) 0.6244(4) 0.2983(2) 0.0478(10) Uani 1 1 d . . . H1A H 0.3483 0.6284 0.2584 0.072 Uiso 1 1 calc R . . H1B H 0.4561 0.6829 0.3035 0.072 Uiso 1 1 calc R . . H1C H 0.2866 0.6588 0.3200 0.072 Uiso 1 1 calc R . . C2 C 0.2961(4) 0.3937(4) 0.31865(14) 0.0315(8) Uani 1 1 d . . . C3 C 0.2686(4) 0.1374(3) 0.33552(14) 0.0297(8) Uani 1 1 d . . . C4 C 0.0262(4) 0.0408(3) 0.32255(14) 0.0286(7) Uani 1 1 d . . . C5 C 0.0418(4) -0.0459(4) 0.27772(15) 0.0364(8) Uani 1 1 d . . . H5 H 0.1226 -0.0355 0.2518 0.044 Uiso 1 1 calc R . . C6 C -0.0606(4) -0.1465(4) 0.27129(16) 0.0391(9) Uani 1 1 d . . . H6 H -0.0484 -0.2078 0.2417 0.047 Uiso 1 1 calc R . . C7 C -0.1809(4) -0.1581(4) 0.30785(17) 0.0411(9) Uani 1 1 d . . . H7 H -0.2529 -0.2254 0.3025 0.049 Uiso 1 1 calc R . . C8 C -0.1972(4) -0.0723(4) 0.35230(16) 0.0357(8) Uani 1 1 d . . . H8 H -0.2802 -0.0803 0.3773 0.043 Uiso 1 1 calc R . . C9 C -0.0915(4) 0.0250(3) 0.35996(14) 0.0273(7) Uani 1 1 d . . . C10 C -0.1704(4) 0.2283(3) 0.41024(14) 0.0267(7) Uani 1 1 d . . . C11 C -0.0976(4) 0.2519(3) 0.50758(14) 0.0287(7) Uani 1 1 d . . . C12 C -0.0392(5) 0.3208(4) 0.59730(15) 0.0412(9) Uani 1 1 d . . . H12A H -0.0831 0.2379 0.6165 0.062 Uiso 1 1 calc R . . H12B H -0.0535 0.4006 0.6207 0.062 Uiso 1 1 calc R . . H12C H 0.0663 0.3026 0.5907 0.062 Uiso 1 1 calc R . . C13 C 0.5940(4) 0.1161(5) 0.2140(2) 0.0533(11) Uani 1 1 d . . . H13A H 0.6339 0.2057 0.1996 0.080 Uiso 1 1 calc R . . H13B H 0.6627 0.0397 0.2045 0.080 Uiso 1 1 calc R . . H13C H 0.5803 0.1157 0.2548 0.080 Uiso 1 1 calc R . . C14 C 0.3582(4) 0.2060(4) 0.18838(15) 0.0360(8) Uani 1 1 d . . . C15 C 0.0970(4) 0.2462(4) 0.16216(14) 0.0324(8) Uani 1 1 d . . . C16 C -0.0277(4) 0.4702(4) 0.17777(14) 0.0290(7) Uani 1 1 d . . . C17 C -0.1348(4) 0.4488(4) 0.21990(16) 0.0368(8) Uani 1 1 d . . . H17 H -0.1246 0.3731 0.2474 0.044 Uiso 1 1 calc R . . C18 C -0.2565(4) 0.5390(4) 0.22136(15) 0.0360(8) Uani 1 1 d . . . H18 H -0.3315 0.5231 0.2494 0.043 Uiso 1 1 calc R . . C19 C -0.2705(4) 0.6516(4) 0.18267(15) 0.0353(8) Uani 1 1 d . . . H19 H -0.3540 0.7134 0.1844 0.042 Uiso 1 1 calc R . . C20 C -0.1625(4) 0.6744(4) 0.14122(15) 0.0314(8) Uani 1 1 d . . . H20 H -0.1706 0.7531 0.1150 0.038 Uiso 1 1 calc R . . C21 C -0.0415(4) 0.5813(4) 0.13814(14) 0.0282(7) Uani 1 1 d . . . C22 C 0.1879(4) 0.6624(3) 0.09506(14) 0.0286(7) Uani 1 1 d . . . C23 C 0.2565(4) 0.6060(3) -0.00153(14) 0.0255(7) Uani 1 1 d . . . C24 C 0.3697(4) 0.5709(4) -0.09037(15) 0.0350(8) Uani 1 1 d . . . H24A H 0.3639 0.4688 -0.0856 0.053 Uiso 1 1 calc R . . H24B H 0.4591 0.5956 -0.1122 0.053 Uiso 1 1 calc R . . H24C H 0.2833 0.6096 -0.1102 0.053 Uiso 1 1 calc R . . N30 N 0.6955(3) -0.4411(3) 0.46854(13) 0.0353(7) Uani 1 1 d . . . C30 C 0.4542(4) -0.0650(3) 0.50764(16) 0.0324(8) Uani 1 1 d . . . H30A H 0.4288 -0.0696 0.5483 0.039 Uiso 1 1 calc R . . H30B H 0.3613 -0.0570 0.4869 0.039 Uiso 1 1 calc R . . C31 C 0.5373(4) -0.1972(3) 0.49343(15) 0.0313(8) Uani 1 1 d . . . C32 C 0.6647(4) -0.2390(3) 0.52128(16) 0.0346(8) Uani 1 1 d . . . H32 H 0.7004 -0.1841 0.5494 0.041 Uiso 1 1 calc R . . C33 C 0.7391(4) -0.3607(4) 0.50792(16) 0.0367(9) Uani 1 1 d . . . H33 H 0.8253 -0.3884 0.5277 0.044 Uiso 1 1 calc R . . C34 C 0.5754(4) -0.4011(3) 0.44133(16) 0.0347(8) Uani 1 1 d . . . H34 H 0.5445 -0.4570 0.4127 0.042 Uiso 1 1 calc R . . C35 C 0.4918(4) -0.2816(3) 0.45248(15) 0.0333(8) Uani 1 1 d . . . H35 H 0.4049 -0.2580 0.4324 0.040 Uiso 1 1 calc R . . N40 N 0.4524(3) 0.1958(3) -0.04171(13) 0.0332(7) Uani 1 1 d . . . C40 C 0.0704(4) -0.0425(4) 0.00783(17) 0.0347(8) Uani 1 1 d . . . H40A H 0.0701 -0.0647 0.0489 0.042 Uiso 1 1 calc R . . H40B H 0.0727 -0.1319 -0.0108 0.042 Uiso 1 1 calc R . . C41 C 0.2052(4) 0.0383(3) -0.00979(15) 0.0294(7) Uani 1 1 d . . . C42 C 0.3066(4) -0.0047(4) -0.05016(15) 0.0312(8) Uani 1 1 d . . . H42 H 0.2934 -0.0895 -0.0676 0.037 Uiso 1 1 calc R . . C43 C 0.4267(4) 0.0760(4) -0.06497(16) 0.0352(8) Uani 1 1 d . . . H43 H 0.4942 0.0450 -0.0930 0.042 Uiso 1 1 calc R . . C44 C 0.3543(4) 0.2374(4) -0.00298(16) 0.0341(8) Uani 1 1 d . . . H44 H 0.3702 0.3227 0.0138 0.041 Uiso 1 1 calc R . . C45 C 0.2314(4) 0.1633(4) 0.01394(16) 0.0346(8) Uani 1 1 d . . . H45 H 0.1650 0.1975 0.0416 0.042 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 S1 0.0484(6) 0.0270(5) 0.0594(7) -0.0020(4) -0.0110(5) 0.0038(4) S2 0.0452(5) 0.0324(5) 0.0297(5) -0.0025(3) -0.0022(4) 0.0100(4) S3 0.0302(5) 0.0559(6) 0.0514(6) -0.0176(5) -0.0016(4) -0.0012(4) S4 0.0381(5) 0.0576(6) 0.0307(5) -0.0154(4) 0.0006(4) -0.0147(4) O1 0.0332(15) 0.0313(13) 0.0595(18) -0.0072(12) -0.0001(13) 0.0038(11) O2 0.0405(15) 0.0265(12) 0.0426(15) -0.0056(10) -0.0026(12) -0.0034(10) O3 0.0568(17) 0.0271(12) 0.0362(14) -0.0105(10) -0.0093(13) 0.0185(12) O4 0.0513(16) 0.0285(12) 0.0320(14) -0.0133(10) -0.0052(12) 0.0101(11) O5 0.0297(14) 0.0541(17) 0.0449(16) -0.0105(13) -0.0021(12) 0.0014(12) O6 0.0290(14) 0.0586(17) 0.0513(17) -0.0086(13) -0.0067(12) 0.0105(12) O7 0.0299(13) 0.0515(15) 0.0323(14) -0.0170(12) 0.0032(11) -0.0152(11) O8 0.0286(13) 0.0452(14) 0.0276(13) -0.0116(10) 0.0052(10) -0.0120(10) N1 0.0344(17) 0.0298(15) 0.0325(17) -0.0029(12) -0.0031(14) 0.0010(13) N2 0.0366(17) 0.0279(15) 0.0339(17) -0.0068(13) 0.0012(14) 0.0037(13) N3 0.0335(16) 0.0274(14) 0.0256(15) -0.0100(12) -0.0014(13) 0.0081(12) N4 0.0366(16) 0.0218(14) 0.0312(16) -0.0079(12) 0.0028(13) 0.0059(12) N5 0.0283(16) 0.0434(18) 0.0374(18) -0.0090(14) 0.0001(13) 0.0037(13) N6 0.0232(15) 0.0445(18) 0.0338(17) -0.0051(13) 0.0009(13) -0.0023(13) N7 0.0302(16) 0.0357(16) 0.0238(15) -0.0082(12) 0.0032(12) -0.0080(12) N8 0.0256(15) 0.0354(16) 0.0303(16) -0.0081(12) 0.0018(13) -0.0107(12) C1 0.048(2) 0.0290(19) 0.066(3) -0.0033(18) 0.002(2) -0.0029(17) C2 0.038(2) 0.0308(18) 0.0270(19) -0.0104(14) 0.0016(15) -0.0028(15) C3 0.039(2) 0.0287(17) 0.0225(17) -0.0078(13) 0.0021(15) -0.0020(15) C4 0.0357(19) 0.0214(16) 0.0295(19) -0.0060(13) -0.0055(15) -0.0019(13) C5 0.043(2) 0.0376(19) 0.029(2) -0.0091(15) 0.0042(17) -0.0008(16) C6 0.048(2) 0.038(2) 0.033(2) -0.0185(16) -0.0066(18) 0.0017(17) C7 0.038(2) 0.041(2) 0.048(2) -0.0209(18) -0.0091(18) -0.0001(17) C8 0.0286(19) 0.038(2) 0.042(2) -0.0126(16) 0.0013(16) -0.0002(15) C9 0.0335(18) 0.0251(16) 0.0235(17) -0.0064(13) -0.0015(14) 0.0069(14) C10 0.0264(17) 0.0247(16) 0.0293(18) -0.0052(13) 0.0013(14) 0.0005(13) C11 0.0333(18) 0.0254(17) 0.0280(18) -0.0103(14) 0.0012(15) 0.0027(14) C12 0.060(3) 0.035(2) 0.030(2) -0.0110(16) -0.0060(18) 0.0084(18) C13 0.028(2) 0.074(3) 0.056(3) 0.002(2) -0.0026(19) 0.010(2) C14 0.0269(19) 0.054(2) 0.0266(19) -0.0022(17) 0.0024(15) 0.0018(17) C15 0.0328(19) 0.043(2) 0.0206(17) -0.0013(15) 0.0042(14) -0.0017(15) C16 0.0262(18) 0.0392(19) 0.0221(17) -0.0058(14) 0.0020(14) -0.0026(14) C17 0.035(2) 0.044(2) 0.032(2) -0.0030(16) 0.0041(16) -0.0036(16) C18 0.0317(19) 0.051(2) 0.0265(19) -0.0099(16) 0.0089(15) -0.0054(16) C19 0.0317(19) 0.042(2) 0.034(2) -0.0169(16) 0.0022(16) -0.0027(15) C20 0.0327(19) 0.0355(18) 0.0271(18) -0.0090(14) -0.0033(15) -0.0033(15) C21 0.0251(17) 0.0390(18) 0.0219(17) -0.0086(14) 0.0013(14) -0.0096(14) C22 0.0255(17) 0.0307(17) 0.0303(19) -0.0054(14) -0.0035(14) -0.0047(13) C23 0.0238(17) 0.0286(16) 0.0248(17) -0.0055(13) -0.0001(13) -0.0038(13) C24 0.034(2) 0.047(2) 0.0248(18) -0.0107(16) 0.0052(15) -0.0059(16) N30 0.0399(18) 0.0270(15) 0.0389(18) -0.0075(13) -0.0002(14) 0.0074(13) C30 0.0350(19) 0.0203(16) 0.041(2) -0.0051(14) 0.0079(16) 0.0067(14) C31 0.037(2) 0.0198(16) 0.036(2) -0.0024(14) 0.0078(16) 0.0041(14) C32 0.044(2) 0.0241(17) 0.036(2) -0.0085(14) -0.0017(16) 0.0047(15) C33 0.042(2) 0.0268(17) 0.042(2) -0.0062(15) -0.0065(17) 0.0083(15) C34 0.042(2) 0.0244(17) 0.039(2) -0.0116(15) -0.0018(17) 0.0004(15) C35 0.0340(19) 0.0271(17) 0.039(2) -0.0036(15) -0.0005(16) 0.0038(14) N40 0.0256(15) 0.0370(16) 0.0377(17) -0.0070(13) 0.0006(13) -0.0043(12) C40 0.0274(19) 0.0318(18) 0.045(2) 0.0005(16) 0.0003(16) -0.0041(15) C41 0.0223(17) 0.0295(17) 0.036(2) -0.0001(14) -0.0050(14) -0.0022(13) C42 0.0262(18) 0.0281(17) 0.040(2) -0.0084(15) -0.0011(15) -0.0020(14) C43 0.0249(18) 0.042(2) 0.039(2) -0.0085(16) 0.0022(16) 0.0007(15) C44 0.0284(18) 0.0336(18) 0.042(2) -0.0106(15) -0.0027(16) -0.0033(14) C45 0.0277(18) 0.040(2) 0.037(2) -0.0112(16) 0.0014(15) -0.0017(15) _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 S1 C3 1.668(3) . ? S2 C10 1.677(3) . ? S3 C15 1.665(4) . ? S4 C22 1.682(3) . ? O1 C2 1.207(4) . ? O2 C2 1.333(4) . ? O2 C1 1.446(4) . ? O3 C11 1.212(4) . ? O4 C11 1.337(4) . ? O4 C12 1.458(4) . ? O5 C14 1.202(5) . ? O6 C14 1.335(4) . ? O6 C13 1.455(5) . ? O7 C23 1.205(4) . ? O8 C23 1.339(4) . ? O8 C24 1.451(4) . ? N1 C2 1.381(5) . ? N1 C3 1.388(5) . ? N2 C3 1.329(5) . ? N2 C4 1.428(5) . ? N3 C10 1.326(4) . ? N3 C9 1.449(4) . ? N4 C11 1.365(4) . ? N4 C10 1.386(4) . ? N5 C14 1.376(5) . ? N5 C15 1.395(5) . ? N6 C15 1.333(5) . ? N6 C16 1.437(4) . ? N7 C22 1.329(4) . ? N7 C21 1.426(4) . ? N8 C23 1.374(4) . ? N8 C22 1.381(4) . ? C4 C9 1.380(5) . ? C4 C5 1.399(5) . ? C5 C6 1.381(6) . ? C6 C7 1.382(6) . ? C7 C8 1.387(5) . ? C8 C9 1.384(5) . ? C16 C21 1.382(5) . ? C16 C17 1.389(5) . ? C17 C18 1.383(5) . ? C18 C19 1.379(5) . ? C19 C20 1.386(5) . ? C20 C21 1.399(5) . ? N30 C34 1.322(5) . ? N30 C33 1.331(5) . ? C30 C31 1.507(4) . ? C30 C30 1.537(7) 2_656 ? C31 C32 1.388(5) . ? C31 C35 1.390(5) . ? C32 C33 1.381(5) . ? C34 C35 1.390(5) . ? N40 C43 1.336(5) . ? N40 C44 1.337(5) . ? C40 C41 1.505(5) . ? C40 C40 1.538(7) 2 ? C41 C42 1.387(5) . ? C41 C45 1.387(5) . ? C42 C43 1.382(5) . ? C44 C45 1.380(5) . ? 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 C2 O2 C1 115.4(3) . . ? C11 O4 C12 115.5(3) . . ? C14 O6 C13 116.2(3) . . ? C23 O8 C24 116.3(3) . . ? C2 N1 C3 127.2(3) . . ? C3 N2 C4 125.6(3) . . ? C10 N3 C9 122.4(3) . . ? C11 N4 C10 127.1(3) . . ? C14 N5 C15 127.7(3) . . ? C15 N6 C16 123.5(3) . . ? C22 N7 C21 123.4(3) . . ? C23 N8 C22 126.7(3) . . ? O1 C2 O2 125.2(3) . . ? O1 C2 N1 125.4(3) . . ? O2 C2 N1 109.5(3) . . ? N2 C3 N1 116.4(3) . . ? N2 C3 S1 125.3(3) . . ? N1 C3 S1 118.3(3) . . ? C9 C4 C5 119.7(3) . . ? C9 C4 N2 120.2(3) . . ? C5 C4 N2 119.9(3) . . ? C6 C5 C4 119.7(4) . . ? C5 C6 C7 120.1(3) . . ? C6 C7 C8 120.4(4) . . ? C9 C8 C7 119.4(4) . . ? C4 C9 C8 120.5(3) . . ? C4 C9 N3 119.6(3) . . ? C8 C9 N3 119.8(3) . . ? N3 C10 N4 117.0(3) . . ? N3 C10 S2 124.4(3) . . ? N4 C10 S2 118.6(2) . . ? O3 C11 O4 124.4(3) . . ? O3 C11 N4 126.8(3) . . ? O4 C11 N4 108.8(3) . . ? O5 C14 O6 125.8(3) . . ? O5 C14 N5 125.5(3) . . ? O6 C14 N5 108.7(3) . . ? N6 C15 N5 116.6(3) . . ? N6 C15 S3 125.6(3) . . ? N5 C15 S3 117.7(3) . . ? C21 C16 C17 120.4(3) . . ? C21 C16 N6 119.8(3) . . ? C17 C16 N6 119.7(3) . . ? C18 C17 C16 119.3(4) . . ? C19 C18 C17 120.9(3) . . ? C18 C19 C20 119.8(3) . . ? C19 C20 C21 119.8(3) . . ? C16 C21 C20 119.7(3) . . ? C16 C21 N7 120.7(3) . . ? C20 C21 N7 119.5(3) . . ? N7 C22 N8 117.3(3) . . ? N7 C22 S4 124.2(3) . . ? N8 C22 S4 118.5(2) . . ? O7 C23 O8 124.7(3) . . ? O7 C23 N8 127.1(3) . . ? O8 C23 N8 108.2(3) . . ? C34 N30 C33 117.8(3) . . ? C31 C30 C30 111.2(4) . 2_656 ? C32 C31 C35 117.2(3) . . ? C32 C31 C30 120.4(3) . . ? C35 C31 C30 122.4(3) . . ? C33 C32 C31 119.7(3) . . ? N30 C33 C32 123.0(3) . . ? N30 C34 C35 123.4(3) . . ? C31 C35 C34 119.0(3) . . ? C43 N40 C44 117.0(3) . . ? C41 C40 C40 110.8(4) . 2 ? C42 C41 C45 116.9(3) . . ? C42 C41 C40 123.1(3) . . ? C45 C41 C40 120.0(3) . . ? C43 C42 C41 120.0(3) . . ? N40 C43 C42 123.0(3) . . ? N40 C44 C45 123.6(3) . . ? C44 C45 C41 119.6(3) . . ? 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 C1 O2 C2 O1 -4.9(5) . . . . ? C1 O2 C2 N1 176.4(3) . . . . ? C3 N1 C2 O1 7.7(6) . . . . ? C3 N1 C2 O2 -173.6(3) . . . . ? C4 N2 C3 N1 175.5(3) . . . . ? C4 N2 C3 S1 -6.2(5) . . . . ? C2 N1 C3 N2 -8.2(5) . . . . ? C2 N1 C3 S1 173.3(3) . . . . ? C3 N2 C4 C9 119.6(4) . . . . ? C3 N2 C4 C5 -65.4(5) . . . . ? C9 C4 C5 C6 0.0(5) . . . . ? N2 C4 C5 C6 -175.0(3) . . . . ? C4 C5 C6 C7 2.3(6) . . . . ? C5 C6 C7 C8 -2.2(6) . . . . ? C6 C7 C8 C9 -0.2(6) . . . . ? C5 C4 C9 C8 -2.4(5) . . . . ? N2 C4 C9 C8 172.5(3) . . . . ? C5 C4 C9 N3 174.0(3) . . . . ? N2 C4 C9 N3 -11.1(5) . . . . ? C7 C8 C9 C4 2.6(5) . . . . ? C7 C8 C9 N3 -173.8(3) . . . . ? C10 N3 C9 C4 92.5(4) . . . . ? C10 N3 C9 C8 -91.1(4) . . . . ? C9 N3 C10 N4 -176.9(3) . . . . ? C9 N3 C10 S2 1.3(5) . . . . ? C11 N4 C10 N3 -2.3(5) . . . . ? C11 N4 C10 S2 179.3(3) . . . . ? C12 O4 C11 O3 0.9(5) . . . . ? C12 O4 C11 N4 -178.2(3) . . . . ? C10 N4 C11 O3 -2.4(6) . . . . ? C10 N4 C11 O4 176.6(3) . . . . ? C13 O6 C14 O5 4.6(6) . . . . ? C13 O6 C14 N5 -176.3(3) . . . . ? C15 N5 C14 O5 -5.9(6) . . . . ? C15 N5 C14 O6 175.0(3) . . . . ? C16 N6 C15 N5 -175.9(3) . . . . ? C16 N6 C15 S3 5.7(5) . . . . ? C14 N5 C15 N6 6.6(6) . . . . ? C14 N5 C15 S3 -174.9(3) . . . . ? C15 N6 C16 C21 -110.0(4) . . . . ? C15 N6 C16 C17 71.7(5) . . . . ? C21 C16 C17 C18 0.8(5) . . . . ? N6 C16 C17 C18 179.1(3) . . . . ? C16 C17 C18 C19 -1.9(5) . . . . ? C17 C18 C19 C20 0.8(5) . . . . ? C18 C19 C20 C21 1.4(5) . . . . ? C17 C16 C21 C20 1.4(5) . . . . ? N6 C16 C21 C20 -176.9(3) . . . . ? C17 C16 C21 N7 -174.9(3) . . . . ? N6 C16 C21 N7 6.8(5) . . . . ? C19 C20 C21 C16 -2.5(5) . . . . ? C19 C20 C21 N7 173.8(3) . . . . ? C22 N7 C21 C16 -86.0(4) . . . . ? C22 N7 C21 C20 97.8(4) . . . . ? C21 N7 C22 N8 176.7(3) . . . . ? C21 N7 C22 S4 -3.6(5) . . . . ? C23 N8 C22 N7 0.6(5) . . . . ? C23 N8 C22 S4 -179.2(3) . . . . ? C24 O8 C23 O7 -0.5(5) . . . . ? C24 O8 C23 N8 178.5(3) . . . . ? C22 N8 C23 O7 -0.1(6) . . . . ? C22 N8 C23 O8 -179.1(3) . . . . ? C30 C30 C31 C32 65.3(5) 2_656 . . . ? C30 C30 C31 C35 -114.5(5) 2_656 . . . ? C35 C31 C32 C33 -0.5(6) . . . . ? C30 C31 C32 C33 179.7(4) . . . . ? C34 N30 C33 C32 0.0(6) . . . . ? C31 C32 C33 N30 0.8(6) . . . . ? C33 N30 C34 C35 -1.2(6) . . . . ? C32 C31 C35 C34 -0.5(5) . . . . ? C30 C31 C35 C34 179.3(3) . . . . ? N30 C34 C35 C31 1.4(6) . . . . ? C40 C40 C41 C42 -115.4(4) 2 . . . ? C40 C40 C41 C45 63.5(5) 2 . . . ? C45 C41 C42 C43 0.0(5) . . . . ? C40 C41 C42 C43 178.9(3) . . . . ? C44 N40 C43 C42 -0.9(5) . . . . ? C41 C42 C43 N40 0.6(6) . . . . ? C43 N40 C44 C45 0.6(5) . . . . ? N40 C44 C45 C41 0.0(6) . . . . ? C42 C41 C45 C44 -0.3(5) . . . . ? C40 C41 C45 C44 -179.2(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 N1 H1N S2 0.83(4) 2.84(4) 3.662(3) 172(4) 1_655 N2 H2N O1 0.80(4) 2.04(4) 2.680(4) 136(4) . N3 H3N O3 0.92(4) 2.00(4) 2.700(4) 132(3) . N3 H3N O3 0.92(4) 2.29(4) 3.081(4) 143(3) 2_556 N4 H4N N30 0.96(4) 1.84(4) 2.788(4) 169(3) 1_465 N6 H6N O5 0.88(4) 2.03(4) 2.703(4) 133(3) . N7 H7N O7 0.89(4) 2.05(4) 2.698(4) 129(3) . N7 H7N O7 0.89(4) 2.34(4) 3.130(4) 148(3) 2_565 N8 H8N N40 0.85(4) 1.97(4) 2.803(4) 170(4) 2_665 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 66.84 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.337 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.080