# Supplementary Material (ESI) for Soft Matter # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 777 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Steed, Jonathan' 'Lloyd, G.' _publ_contact_author_name 'Steed, Jonathan' _publ_contact_author_email jon.steed@durham.ac.uk _publ_section_title ; Anion Tuning of the Rheology, Morphology and Gelation of a Low Molecular Weight Salt Hydrogelator ; # Attachment '- 1 SO4.CIF' data_1SO4.CIF _database_code_depnum_ccdc_archive 'CCDC 783190' #TrackingRef '- 1 SO4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3.10H+)2(SO42).7H2O ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H38 N10 O17 S' _chemical_formula_weight 746.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 8.60190(10) _cell_length_b 16.2504(2) _cell_length_c 23.2724(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.1000(10) _cell_angle_gamma 90.00 _cell_volume 3252.52(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9308 _exptl_absorpt_correction_T_max 0.9555 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SMART1000 _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 33366 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 30.52 _reflns_number_total 9934 _reflns_number_gt 7653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Software' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _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^)+(0.0879P)^2^+1.2032P] 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 9934 _refine_ls_number_parameters 503 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1555 _refine_ls_wR_factor_gt 0.1414 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.129 _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 0.20133(5) 0.51058(2) 0.400818(17) 0.01750(10) Uani 1 1 d . . . O1 O 0.42053(19) 0.56368(8) 0.26966(6) 0.0305(3) Uani 1 1 d D . . N1 N 0.17171(17) 0.71473(9) 0.31312(6) 0.0191(3) Uani 1 1 d . . . H1N H 0.1620 0.6754 0.3388 0.023 Uiso 1 1 calc R . . C1 C 0.0017(2) 0.81186(11) 0.36393(7) 0.0229(3) Uani 1 1 d . . . H1A H -0.0314 0.7621 0.3841 0.034 Uiso 1 1 calc R . . H1B H -0.0900 0.8414 0.3492 0.034 Uiso 1 1 calc R . . H1C H 0.0602 0.8474 0.3906 0.034 Uiso 1 1 calc R . . H1WA H 0.389(4) 0.5304(18) 0.3009(10) 0.067(10) Uiso 1 1 d D . . H1WB H 0.5303(7) 0.563(3) 0.266(2) 0.122(18) Uiso 1 1 d D . . O2 O 0.84315(17) 0.59457(9) 0.45591(6) 0.0299(3) Uani 1 1 d D . . N2 N 0.25912(17) 0.70979(8) 0.26544(6) 0.0186(3) Uani 1 1 d . . . H2N H 0.3145 0.6670 0.2549 0.022 Uiso 1 1 calc R . . C2 C 0.1022(2) 0.78858(10) 0.31525(7) 0.0182(3) Uani 1 1 d . . . H2WA H 0.862(3) 0.5716(16) 0.4929(5) 0.047(8) Uiso 1 1 d D . . H2WB H 0.9369(18) 0.5945(19) 0.4350(11) 0.054(8) Uiso 1 1 d D . . H3WB H 0.144(4) 0.517(3) 0.2641(19) 0.14(2) Uiso 1 1 d D . . O3 O 0.0599(2) 0.50736(10) 0.23807(8) 0.0376(4) Uani 1 1 d D . . N3 N 0.31983(17) 0.79847(8) 0.18644(6) 0.0173(3) Uani 1 1 d . . . H3N H 0.2995 0.8451 0.1686 0.021 Uiso 1 1 calc R . . C3 C 0.1475(2) 0.83332(10) 0.26745(7) 0.0183(3) Uani 1 1 d . . . H3 H 0.1173 0.8878 0.2575 0.022 Uiso 1 1 calc R . . H3WA H 0.123(4) 0.509(2) 0.2049(10) 0.083(12) Uiso 1 1 d D . . O4 O -0.2388(2) 0.56780(9) 0.27231(7) 0.0345(3) Uani 1 1 d D . . N4 N 0.48458(17) 0.76859(8) 0.11168(6) 0.0182(3) Uani 1 1 d . . . H4N H 0.4556 0.8168 0.0980 0.022 Uiso 1 1 calc R . . C4 C 0.24661(19) 0.78151(9) 0.23704(7) 0.0166(3) Uani 1 1 d . . . H4WA H -0.144(3) 0.564(3) 0.2525(17) 0.110(16) Uiso 1 1 d D . . H4WB H -0.217(6) 0.534(3) 0.3049(13) 0.126(18) Uiso 1 1 d D . . O5 O -0.20295(16) 0.45037(8) 0.36125(6) 0.0246(3) Uani 1 1 d D . . N5 N 0.81843(18) 0.52761(9) 0.08100(7) 0.0231(3) Uani 1 1 d . . . C5 C 0.42487(19) 0.74411(10) 0.16276(7) 0.0180(3) Uani 1 1 d . . . H5WA H -0.1028(18) 0.450(2) 0.3791(14) 0.073(11) Uiso 1 1 d D . . H5WB H -0.276(3) 0.4596(19) 0.3908(9) 0.054(9) Uiso 1 1 d D . . O6 O -0.41349(14) 0.42494(7) 0.44505(5) 0.0235(3) Uani 1 1 d D . . N6 N 0.62147(18) 0.74440(9) 0.32434(6) 0.0200(3) Uani 1 1 d . . . H6N H 0.6005 0.7060 0.3497 0.024 Uiso 1 1 calc R . . C6 C 0.58985(19) 0.72178(10) 0.07917(7) 0.0177(3) Uani 1 1 d . . . O7 O 0.57316(17) 0.63014(9) 0.40266(6) 0.0316(3) Uani 1 1 d D . . N7 N 0.71180(18) 0.73427(9) 0.27772(6) 0.0197(3) Uani 1 1 d . . . H7N H 0.7604 0.6888 0.2682 0.024 Uiso 1 1 calc R . . C7 C 0.6522(2) 0.64658(10) 0.09733(7) 0.0186(3) Uani 1 1 d . . . H7 H 0.6267 0.6238 0.1335 0.022 Uiso 1 1 calc R . . H7WA H 0.485(2) 0.5974(16) 0.4108(13) 0.059(9) Uiso 1 1 d D . . H7WB H 0.659(2) 0.6111(19) 0.4251(11) 0.061(9) Uiso 1 1 d D . . O8 O 0.45882(16) 0.67998(8) 0.18712(5) 0.0273(3) Uani 1 1 d . . . N8 N 0.79095(17) 0.81724(8) 0.19800(6) 0.0195(3) Uani 1 1 d . . . H8N H 0.7765 0.8638 0.1794 0.023 Uiso 1 1 calc R . . C8 C 0.75252(19) 0.60632(10) 0.06087(7) 0.0189(3) Uani 1 1 d . . . O9 O 0.7976(2) 0.50678(9) 0.13082(6) 0.0345(3) Uani 1 1 d . . . N9 N 0.95525(17) 0.78608(8) 0.12510(6) 0.0186(3) Uani 1 1 d . . . H9N H 0.9302 0.8360 0.1136 0.022 Uiso 1 1 calc R . . C9 C 0.7954(2) 0.63578(11) 0.00771(7) 0.0219(3) Uani 1 1 d . . . H9 H 0.8634 0.6058 -0.0162 0.026 Uiso 1 1 calc R . . O10 O 0.89303(19) 0.48682(9) 0.04686(7) 0.0341(3) Uani 1 1 d . . . N10 N 1.27615(19) 0.54471(9) 0.08051(7) 0.0243(3) Uani 1 1 d . . . C10 C 0.7339(2) 0.71161(11) -0.00890(7) 0.0233(3) Uani 1 1 d . . . H10 H 0.7618 0.7346 -0.0448 0.028 Uiso 1 1 calc R . . O11 O 0.91369(15) 0.69266(7) 0.19743(5) 0.0216(2) Uani 1 1 d . . . C11 C 0.6328(2) 0.75398(11) 0.02598(7) 0.0209(3) Uani 1 1 d . . . H11 H 0.5921 0.8055 0.0137 0.025 Uiso 1 1 calc R . . O12 O 1.2201(2) 0.50743(9) 0.12137(7) 0.0368(4) Uani 1 1 d . . . C12 C 0.4709(2) 0.85152(11) 0.37364(8) 0.0248(3) Uani 1 1 d . . . H12A H 0.4282 0.8042 0.3941 0.037 Uiso 1 1 calc R . . H12B H 0.3855 0.8852 0.3580 0.037 Uiso 1 1 calc R . . H12C H 0.5344 0.8847 0.4003 0.037 Uiso 1 1 calc R . . O13 O 1.38038(18) 0.51689(9) 0.05118(7) 0.0318(3) Uani 1 1 d . . . C13 C 0.5692(2) 0.82194(10) 0.32571(7) 0.0193(3) Uani 1 1 d . . . O14 O 0.26705(19) 0.47497(9) 0.34799(6) 0.0325(3) Uani 1 1 d . . . C14 C 0.6258(2) 0.86308(10) 0.27824(7) 0.0196(3) Uani 1 1 d . . . H14 H 0.6081 0.9189 0.2680 0.024 Uiso 1 1 calc R . . O15 O 0.09302(15) 0.45026(8) 0.42586(6) 0.0235(3) Uani 1 1 d . . . C15 C 0.71427(19) 0.80537(10) 0.24865(7) 0.0181(3) Uani 1 1 d . . . O16 O 0.32915(16) 0.52878(9) 0.44193(6) 0.0270(3) Uani 1 1 d . . . C16 C 0.88988(19) 0.75928(10) 0.17490(7) 0.0178(3) Uani 1 1 d . . . O17 O 0.11674(16) 0.58717(8) 0.38727(6) 0.0277(3) Uani 1 1 d . . . C17 C 1.05822(19) 0.74202(10) 0.09052(7) 0.0184(3) Uani 1 1 d . . . C18 C 1.1137(2) 0.66337(10) 0.10414(7) 0.0192(3) Uani 1 1 d . . . H18 H 1.0831 0.6359 0.1381 0.023 Uiso 1 1 calc R . . C19 C 1.2151(2) 0.62712(10) 0.06606(7) 0.0203(3) Uani 1 1 d . . . C20 C 1.2640(2) 0.66321(11) 0.01578(7) 0.0224(3) Uani 1 1 d . . . H20 H 1.3325 0.6355 -0.0093 0.027 Uiso 1 1 calc R . . C21 C 1.2087(2) 0.74185(11) 0.00346(7) 0.0227(3) Uani 1 1 d . . . H21 H 1.2403 0.7688 -0.0306 0.027 Uiso 1 1 calc R . . C22 C 1.10499(18) 0.78248(10) 0.04130(6) 0.0209(3) Uani 1 1 d . . . H22 H 1.0686 0.8364 0.0329 0.025 Uiso 1 1 calc R . . H6WA H -0.3753 0.4384 0.4800 0.051(8) Uiso 1 1 d RD . . H6WB H -0.4963 0.4579 0.4428 0.036(7) Uiso 1 1 d RD . . 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 0.0177(2) 0.01757(18) 0.01738(18) 0.00176(13) 0.00324(14) -0.00229(13) O1 0.0415(9) 0.0229(6) 0.0273(7) 0.0063(5) 0.0092(6) 0.0051(6) N1 0.0222(7) 0.0187(6) 0.0164(6) 0.0028(5) 0.0039(5) 0.0006(5) C1 0.0218(8) 0.0265(8) 0.0205(8) -0.0016(6) 0.0040(6) 0.0003(6) O2 0.0262(7) 0.0400(8) 0.0235(6) -0.0006(5) 0.0009(5) 0.0064(6) N2 0.0209(7) 0.0175(6) 0.0176(6) 0.0012(5) 0.0042(5) 0.0018(5) C2 0.0177(7) 0.0186(7) 0.0183(7) -0.0006(5) 0.0000(6) -0.0005(6) O3 0.0316(8) 0.0350(8) 0.0462(9) 0.0043(7) 0.0032(7) 0.0022(6) N3 0.0200(7) 0.0163(6) 0.0155(6) 0.0026(5) 0.0020(5) 0.0014(5) C3 0.0190(8) 0.0171(7) 0.0190(7) 0.0002(5) 0.0006(6) 0.0001(6) O4 0.0434(9) 0.0241(6) 0.0367(8) 0.0067(6) 0.0169(7) 0.0073(6) N4 0.0197(7) 0.0176(6) 0.0173(6) 0.0020(5) 0.0025(5) 0.0017(5) C4 0.0176(7) 0.0168(7) 0.0153(7) 0.0002(5) -0.0006(5) -0.0013(5) O5 0.0234(7) 0.0235(6) 0.0269(6) -0.0052(5) 0.0007(5) -0.0009(5) N5 0.0209(7) 0.0184(6) 0.0299(8) -0.0010(5) 0.0018(6) 0.0004(5) C5 0.0171(7) 0.0199(7) 0.0171(7) 0.0004(5) 0.0001(5) -0.0008(6) O6 0.0237(6) 0.0214(6) 0.0253(6) -0.0028(5) -0.0007(5) 0.0003(5) N6 0.0226(7) 0.0195(6) 0.0181(6) 0.0015(5) 0.0036(5) -0.0011(5) C6 0.0160(7) 0.0183(7) 0.0188(7) -0.0004(5) 0.0009(6) -0.0016(5) O7 0.0265(7) 0.0353(7) 0.0329(7) 0.0149(6) -0.0021(6) -0.0071(6) N7 0.0237(7) 0.0168(6) 0.0185(6) 0.0015(5) 0.0030(5) 0.0000(5) C7 0.0183(8) 0.0178(7) 0.0197(7) 0.0004(5) 0.0005(6) -0.0010(6) O8 0.0321(7) 0.0247(6) 0.0254(6) 0.0092(5) 0.0095(5) 0.0101(5) N8 0.0225(7) 0.0173(6) 0.0189(6) 0.0034(5) 0.0021(5) 0.0017(5) C8 0.0178(8) 0.0159(7) 0.0229(7) -0.0010(6) -0.0010(6) -0.0011(6) O9 0.0461(9) 0.0258(7) 0.0319(7) 0.0072(5) 0.0082(7) 0.0086(6) N9 0.0195(7) 0.0169(6) 0.0196(6) 0.0017(5) 0.0027(5) 0.0012(5) C9 0.0202(8) 0.0229(8) 0.0228(8) -0.0035(6) 0.0030(6) -0.0003(6) O10 0.0373(8) 0.0290(7) 0.0363(8) -0.0030(6) 0.0059(6) 0.0121(6) N10 0.0242(8) 0.0181(6) 0.0307(8) -0.0018(6) 0.0010(6) 0.0003(6) C10 0.0226(9) 0.0273(8) 0.0201(8) 0.0021(6) 0.0045(6) 0.0004(7) O11 0.0255(6) 0.0174(5) 0.0218(6) 0.0021(4) 0.0015(5) 0.0008(5) C11 0.0203(8) 0.0227(7) 0.0199(7) 0.0032(6) 0.0030(6) 0.0010(6) O12 0.0433(9) 0.0241(7) 0.0436(8) 0.0096(6) 0.0137(7) 0.0059(6) C12 0.0231(9) 0.0273(8) 0.0242(8) -0.0021(6) 0.0034(7) -0.0009(7) O13 0.0289(7) 0.0269(7) 0.0399(8) -0.0038(6) 0.0064(6) 0.0070(5) C13 0.0174(7) 0.0196(7) 0.0209(7) -0.0014(6) 0.0001(6) -0.0014(6) O14 0.0421(9) 0.0298(7) 0.0263(7) -0.0075(5) 0.0151(6) -0.0117(6) C14 0.0188(8) 0.0173(7) 0.0228(8) 0.0010(6) 0.0005(6) 0.0005(6) O15 0.0236(6) 0.0220(6) 0.0251(6) 0.0031(5) 0.0047(5) -0.0058(5) C15 0.0181(7) 0.0174(7) 0.0188(7) 0.0008(5) -0.0013(6) -0.0011(6) O16 0.0226(7) 0.0316(7) 0.0268(6) -0.0002(5) -0.0011(5) -0.0039(5) C16 0.0166(7) 0.0187(7) 0.0181(7) -0.0011(5) -0.0013(5) -0.0023(6) O17 0.0250(7) 0.0242(6) 0.0340(7) 0.0120(5) 0.0052(5) 0.0031(5) C17 0.0159(7) 0.0196(7) 0.0197(7) -0.0017(5) -0.0010(6) -0.0024(6) C18 0.0177(8) 0.0183(7) 0.0215(7) -0.0002(6) 0.0004(6) -0.0017(6) C19 0.0192(8) 0.0161(7) 0.0254(8) -0.0022(6) -0.0016(6) 0.0005(6) C20 0.0226(8) 0.0221(8) 0.0228(8) -0.0039(6) 0.0027(6) -0.0009(6) C21 0.0253(9) 0.0237(8) 0.0194(7) 0.0004(6) 0.0020(6) -0.0011(6) C22 0.0203(8) 0.0223(7) 0.0202(7) 0.0002(6) 0.0000(6) -0.0002(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 O17 1.4728(13) . ? S1 O16 1.4735(14) . ? S1 O15 1.4797(13) . ? S1 O14 1.4808(14) . ? O1 H1WA 0.95(3) . ? O1 H1WB 0.950(7) . ? N1 C2 1.342(2) . ? N1 N2 1.3546(19) . ? N1 H1N 0.8800 . ? C1 C2 1.487(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 H2WA 0.95(3) . ? O2 H2WB 0.95(3) . ? N2 C4 1.343(2) . ? N2 H2N 0.8800 . ? C2 C3 1.391(2) . ? O3 H3WB 0.95(3) . ? O3 H3WA 0.95(3) . ? N3 C4 1.374(2) . ? N3 C5 1.385(2) . ? N3 H3N 0.8800 . ? C3 C4 1.400(2) . ? C3 H3 0.9500 . ? O4 H4WA 0.95(3) . ? O4 H4WB 0.95(3) . ? N4 C5 1.363(2) . ? N4 C6 1.413(2) . ? N4 H4N 0.8800 . ? O5 H5WA 0.95(2) . ? O5 H5WB 0.95(3) . ? N5 O9 1.224(2) . ? N5 O10 1.226(2) . ? N5 C8 1.472(2) . ? C5 O8 1.219(2) . ? O6 H6WA 0.8979 . ? O6 H6WB 0.8921 . ? N6 C13 1.338(2) . ? N6 N7 1.3565(19) . ? N6 H6N 0.8800 . ? C6 C7 1.397(2) . ? C6 C11 1.400(2) . ? O7 H7WA 0.95(2) . ? O7 H7WB 0.95(2) . ? N7 C15 1.339(2) . ? N7 H7N 0.8800 . ? C7 C8 1.386(2) . ? C7 H7 0.9500 . ? N8 C15 1.375(2) . ? N8 C16 1.385(2) . ? N8 H8N 0.8800 . ? C8 C9 1.383(2) . ? N9 C16 1.369(2) . ? N9 C17 1.404(2) . ? N9 H9N 0.8800 . ? C9 C10 1.393(2) . ? C9 H9 0.9500 . ? N10 O13 1.224(2) . ? N10 O12 1.234(2) . ? N10 C19 1.475(2) . ? C10 C11 1.384(2) . ? C10 H10 0.9500 . ? O11 C16 1.219(2) . ? C11 H11 0.9500 . ? C12 C13 1.492(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.387(2) . ? C14 C15 1.397(2) . ? C14 H14 0.9500 . ? C17 C22 1.387(2) . ? C17 C18 1.399(2) . ? C18 C19 1.387(2) . ? C18 H18 0.9500 . ? C19 C20 1.382(2) . ? C20 C21 1.392(2) . ? C20 H20 0.9500 . ? C21 C22 1.427(2) . ? C21 H21 0.9500 . ? C22 H22 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 O17 S1 O16 109.20(8) . . ? O17 S1 O15 109.39(8) . . ? O16 S1 O15 110.17(8) . . ? O17 S1 O14 110.33(9) . . ? O16 S1 O14 108.99(9) . . ? O15 S1 O14 108.75(8) . . ? H1WA O1 H1WB 111(4) . . ? C2 N1 N2 109.75(13) . . ? C2 N1 H1N 125.1 . . ? N2 N1 H1N 125.1 . . ? 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 . . ? H2WA O2 H2WB 110(3) . . ? C4 N2 N1 108.13(13) . . ? C4 N2 H2N 125.9 . . ? N1 N2 H2N 125.9 . . ? N1 C2 C3 107.84(14) . . ? N1 C2 C1 121.43(15) . . ? C3 C2 C1 130.69(15) . . ? H3WB O3 H3WA 94(4) . . ? C4 N3 C5 121.74(13) . . ? C4 N3 H3N 119.1 . . ? C5 N3 H3N 119.1 . . ? C2 C3 C4 105.80(14) . . ? C2 C3 H3 127.1 . . ? C4 C3 H3 127.1 . . ? H4WA O4 H4WB 101(4) . . ? C5 N4 C6 124.45(14) . . ? C5 N4 H4N 117.8 . . ? C6 N4 H4N 117.8 . . ? N2 C4 N3 124.20(15) . . ? N2 C4 C3 108.48(14) . . ? N3 C4 C3 127.31(14) . . ? H5WA O5 H5WB 107(3) . . ? O9 N5 O10 123.53(16) . . ? O9 N5 C8 118.63(15) . . ? O10 N5 C8 117.84(15) . . ? O8 C5 N4 124.34(15) . . ? O8 C5 N3 120.81(15) . . ? N4 C5 N3 114.85(14) . . ? H6WA O6 H6WB 100.7 . . ? C13 N6 N7 109.34(14) . . ? C13 N6 H6N 125.3 . . ? N7 N6 H6N 125.3 . . ? C7 C6 C11 119.22(15) . . ? C7 C6 N4 123.72(14) . . ? C11 C6 N4 117.06(14) . . ? H7WA O7 H7WB 109(3) . . ? C15 N7 N6 108.32(14) . . ? C15 N7 H7N 125.8 . . ? N6 N7 H7N 125.8 . . ? C8 C7 C6 117.88(15) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C15 N8 C16 123.07(14) . . ? C15 N8 H8N 118.5 . . ? C16 N8 H8N 118.5 . . ? C9 C8 C7 124.35(15) . . ? C9 C8 N5 118.53(15) . . ? C7 C8 N5 117.12(15) . . ? C16 N9 C17 126.64(14) . . ? C16 N9 H9N 116.7 . . ? C17 N9 H9N 116.7 . . ? C8 C9 C10 116.61(15) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? O13 N10 O12 123.37(16) . . ? O13 N10 C19 118.02(15) . . ? O12 N10 C19 118.61(15) . . ? C11 C10 C9 121.12(16) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 120.80(16) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N6 C13 C14 108.15(15) . . ? N6 C13 C12 121.10(15) . . ? C14 C13 C12 130.73(15) . . ? C13 C14 C15 105.77(14) . . ? C13 C14 H14 127.1 . . ? C15 C14 H14 127.1 . . ? N7 C15 N8 124.51(15) . . ? N7 C15 C14 108.41(14) . . ? N8 C15 C14 127.08(15) . . ? O11 C16 N9 125.35(15) . . ? O11 C16 N8 122.45(15) . . ? N9 C16 N8 112.19(14) . . ? C22 C17 C18 121.14(15) . . ? C22 C17 N9 115.33(14) . . ? C18 C17 N9 123.52(15) . . ? C19 C18 C17 117.35(15) . . ? C19 C18 H18 121.3 . . ? C17 C18 H18 121.3 . . ? C20 C19 C18 124.50(16) . . ? C20 C19 N10 117.75(15) . . ? C18 C19 N10 117.75(15) . . ? C19 C20 C21 117.11(16) . . ? C19 C20 H20 121.4 . . ? C21 C20 H20 121.4 . . ? C20 C21 C22 120.86(16) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C17 C22 C21 119.01(15) . . ? C17 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? 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 C2 N1 N2 C4 0.58(18) . . . . ? N2 N1 C2 C3 -0.55(19) . . . . ? N2 N1 C2 C1 -178.50(15) . . . . ? N1 C2 C3 C4 0.30(19) . . . . ? C1 C2 C3 C4 177.99(17) . . . . ? N1 N2 C4 N3 -179.88(15) . . . . ? N1 N2 C4 C3 -0.38(18) . . . . ? C5 N3 C4 N2 -5.6(2) . . . . ? C5 N3 C4 C3 175.02(16) . . . . ? C2 C3 C4 N2 0.05(19) . . . . ? C2 C3 C4 N3 179.53(16) . . . . ? C6 N4 C5 O8 2.2(3) . . . . ? C6 N4 C5 N3 -178.06(14) . . . . ? C4 N3 C5 O8 -2.0(2) . . . . ? C4 N3 C5 N4 178.29(14) . . . . ? C5 N4 C6 C7 -3.8(3) . . . . ? C5 N4 C6 C11 176.40(15) . . . . ? C13 N6 N7 C15 -1.28(19) . . . . ? C11 C6 C7 C8 -1.2(2) . . . . ? N4 C6 C7 C8 179.05(15) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C6 C7 C8 N5 179.35(14) . . . . ? O9 N5 C8 C9 170.33(17) . . . . ? O10 N5 C8 C9 -8.9(2) . . . . ? O9 N5 C8 C7 -8.9(2) . . . . ? O10 N5 C8 C7 171.94(16) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? N5 C8 C9 C10 -178.17(15) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C6 0.2(3) . . . . ? C7 C6 C11 C10 1.0(3) . . . . ? N4 C6 C11 C10 -179.21(16) . . . . ? N7 N6 C13 C14 0.69(19) . . . . ? N7 N6 C13 C12 -177.89(15) . . . . ? N6 C13 C14 C15 0.12(19) . . . . ? C12 C13 C14 C15 178.52(17) . . . . ? N6 N7 C15 N8 -178.09(15) . . . . ? N6 N7 C15 C14 1.34(19) . . . . ? C16 N8 C15 N7 -8.0(3) . . . . ? C16 N8 C15 C14 172.73(16) . . . . ? C13 C14 C15 N7 -0.90(19) . . . . ? C13 C14 C15 N8 178.51(16) . . . . ? C17 N9 C16 O11 1.3(3) . . . . ? C17 N9 C16 N8 -178.84(15) . . . . ? C15 N8 C16 O11 1.5(3) . . . . ? C15 N8 C16 N9 -178.45(15) . . . . ? C16 N9 C17 C22 178.49(15) . . . . ? C16 N9 C17 C18 -2.5(3) . . . . ? C22 C17 C18 C19 -1.0(2) . . . . ? N9 C17 C18 C19 -179.91(15) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C17 C18 C19 N10 179.06(14) . . . . ? O13 N10 C19 C20 8.6(2) . . . . ? O12 N10 C19 C20 -171.46(17) . . . . ? O13 N10 C19 C18 -170.80(16) . . . . ? O12 N10 C19 C18 9.1(2) . . . . ? C18 C19 C20 C21 1.0(3) . . . . ? N10 C19 C20 C21 -178.36(15) . . . . ? C19 C20 C21 C22 -0.5(3) . . . . ? C18 C17 C22 C21 1.5(2) . . . . ? N9 C17 C22 C21 -179.50(14) . . . . ? C20 C21 C22 C17 -0.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.246 _refine_diff_density_min -0.952 _refine_diff_density_rms 0.080 # Attachment '- 1.CIF' data_z:\xraydata\gareth\09srv209\work\srv209m _database_code_depnum_ccdc_archive 'CCDC 783191' #TrackingRef '- 1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N5 O3' _chemical_formula_sum 'C11 H11 N5 O3' _chemical_formula_weight 261.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4699(10) _cell_length_b 5.4899(5) _cell_length_c 20.581(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.507(4) _cell_angle_gamma 90.00 _cell_volume 1150.26(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2887 _cell_measurement_theta_min 2.248 _cell_measurement_theta_max 30.248 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5356 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Smart-6K _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10993 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 30.49 _reflns_number_total 3450 _reflns_number_gt 2428 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0759P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3450 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O1 O 0.16308(10) 0.45714(19) 0.05653(5) 0.0311(3) Uani 1 1 d . . . O3 O 0.76303(10) -0.3354(2) 0.16798(5) 0.0336(3) Uani 1 1 d . . . O2 O 0.64367(11) -0.4335(2) 0.07059(5) 0.0348(3) Uani 1 1 d . . . N4 N 0.25825(12) 0.1059(2) 0.02988(6) 0.0269(3) Uani 1 1 d . . . H4 H 0.2457 -0.0168 0.0016 0.032 Uiso 1 1 calc R . . N5 N 0.66718(12) -0.3052(2) 0.12035(6) 0.0271(3) Uani 1 1 d . . . C8 C 0.57706(13) -0.1045(3) 0.12510(7) 0.0244(3) Uani 1 1 d . . . N3 N 0.06339(12) 0.2496(2) -0.03623(6) 0.0283(3) Uani 1 1 d . . . H3 H 0.0015 0.3615 -0.0426 0.034 Uiso 1 1 calc R . . C2 C -0.06549(14) 0.0378(3) -0.13721(7) 0.0270(3) Uani 1 1 d . . . H2 H -0.1419 0.1371 -0.1475 0.032 Uiso 1 1 calc R . . C9 C 0.61213(14) 0.0580(3) 0.17768(7) 0.0275(3) Uani 1 1 d . . . H9 H 0.6927 0.0428 0.2102 0.033 Uiso 1 1 calc R . . C7 C 0.46087(13) -0.0906(3) 0.07669(7) 0.0248(3) Uani 1 1 d . . . H7 H 0.4407 -0.2073 0.0417 0.030 Uiso 1 1 calc R . . N2 N 0.13616(12) -0.1030(2) -0.08471(6) 0.0296(3) Uani 1 1 d . . . C5 C 0.16263(14) 0.2810(3) 0.01939(7) 0.0261(3) Uani 1 1 d . . . C6 C 0.37362(13) 0.0997(3) 0.08043(7) 0.0243(3) Uani 1 1 d . . . C10 C 0.52415(14) 0.2440(3) 0.18066(7) 0.0285(3) Uani 1 1 d . . . H10 H 0.5447 0.3585 0.2162 0.034 Uiso 1 1 calc R . . C1 C -0.03942(14) -0.1661(3) -0.17077(7) 0.0277(3) Uani 1 1 d . . . C3 C 0.04575(13) 0.0668(3) -0.08433(7) 0.0253(3) Uani 1 1 d . . . C11 C 0.40657(14) 0.2672(3) 0.13296(7) 0.0274(3) Uani 1 1 d . . . H11 H 0.3484 0.3972 0.1360 0.033 Uiso 1 1 calc R . . N1 N 0.08124(12) -0.2437(2) -0.13861(6) 0.0294(3) Uani 1 1 d . . . H1 H 0.1203 -0.3715 -0.1511 0.035 Uiso 1 1 calc R . . C4 C -0.11928(16) -0.2990(3) -0.22946(8) 0.0345(4) Uani 1 1 d . . . H4A H -0.1004 -0.2340 -0.2706 0.052 Uiso 1 1 calc R . . H4B H -0.2128 -0.2778 -0.2308 0.052 Uiso 1 1 calc R . . H4C H -0.0972 -0.4727 -0.2256 0.052 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 O1 0.0285(5) 0.0295(5) 0.0324(5) -0.0030(4) 0.0015(4) 0.0111(4) O3 0.0262(5) 0.0391(6) 0.0329(6) 0.0049(5) 0.0012(4) 0.0122(4) O2 0.0340(6) 0.0385(6) 0.0316(6) -0.0011(5) 0.0070(5) 0.0140(5) N4 0.0241(6) 0.0277(6) 0.0269(6) -0.0002(5) 0.0019(5) 0.0095(5) N5 0.0231(6) 0.0300(6) 0.0285(6) 0.0056(5) 0.0068(5) 0.0090(5) C8 0.0216(6) 0.0263(7) 0.0265(6) 0.0056(5) 0.0078(5) 0.0081(5) N3 0.0246(6) 0.0279(6) 0.0295(6) -0.0015(5) 0.0005(5) 0.0121(5) C2 0.0229(6) 0.0281(7) 0.0294(7) 0.0023(5) 0.0049(5) 0.0059(5) C9 0.0224(6) 0.0303(7) 0.0282(7) 0.0024(6) 0.0028(5) 0.0030(5) C7 0.0247(7) 0.0266(7) 0.0230(6) 0.0025(5) 0.0053(5) 0.0064(5) N2 0.0269(6) 0.0299(6) 0.0305(6) -0.0033(5) 0.0036(5) 0.0102(5) C5 0.0244(7) 0.0265(7) 0.0270(7) 0.0028(5) 0.0050(5) 0.0074(5) C6 0.0218(6) 0.0270(7) 0.0240(6) 0.0045(5) 0.0049(5) 0.0061(5) C10 0.0269(7) 0.0278(7) 0.0294(7) -0.0019(5) 0.0035(6) 0.0017(5) C1 0.0245(7) 0.0290(7) 0.0295(7) 0.0033(6) 0.0058(6) 0.0040(5) C3 0.0234(7) 0.0265(7) 0.0263(7) 0.0030(5) 0.0064(5) 0.0071(5) C11 0.0241(7) 0.0266(7) 0.0313(7) 0.0014(6) 0.0059(6) 0.0070(5) N1 0.0260(6) 0.0291(6) 0.0316(6) -0.0034(5) 0.0040(5) 0.0085(5) C4 0.0305(8) 0.0325(8) 0.0381(8) -0.0060(6) 0.0033(6) 0.0028(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 O1 C5 1.2320(17) . ? O3 N5 1.2394(15) . ? O2 N5 1.2195(16) . ? N4 C5 1.3680(17) . ? N4 C6 1.3984(17) . ? N4 H4 0.8800 . ? N5 C8 1.4688(17) . ? C8 C7 1.3828(19) . ? C8 C9 1.384(2) . ? N3 C5 1.3653(18) . ? N3 C3 1.3916(19) . ? N3 H3 0.8800 . ? C2 C1 1.376(2) . ? C2 C3 1.4050(19) . ? C2 H2 0.9500 . ? C9 C10 1.386(2) . ? C9 H9 0.9500 . ? C7 C6 1.4017(19) . ? C7 H7 0.9500 . ? N2 C3 1.3297(18) . ? N2 N1 1.3639(17) . ? C6 C11 1.400(2) . ? C10 C11 1.3896(19) . ? C10 H10 0.9500 . ? C1 N1 1.3509(18) . ? C1 C4 1.489(2) . ? C11 H11 0.9500 . ? N1 H1 0.8800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 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 C5 N4 C6 127.41(12) . . ? C5 N4 H4 116.3 . . ? C6 N4 H4 116.3 . . ? O2 N5 O3 123.66(12) . . ? O2 N5 C8 118.83(11) . . ? O3 N5 C8 117.50(12) . . ? C7 C8 C9 123.76(12) . . ? C7 C8 N5 117.65(12) . . ? C9 C8 N5 118.58(12) . . ? C5 N3 C3 129.49(12) . . ? C5 N3 H3 115.3 . . ? C3 N3 H3 115.3 . . ? C1 C2 C3 104.79(12) . . ? C1 C2 H2 127.6 . . ? C3 C2 H2 127.6 . . ? C8 C9 C10 116.85(13) . . ? C8 C9 H9 121.6 . . ? C10 C9 H9 121.6 . . ? C8 C7 C6 118.46(13) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C3 N2 N1 103.67(11) . . ? O1 C5 N3 120.73(12) . . ? O1 C5 N4 123.84(13) . . ? N3 C5 N4 115.42(12) . . ? N4 C6 C11 124.95(12) . . ? N4 C6 C7 115.98(12) . . ? C11 C6 C7 119.06(12) . . ? C9 C10 C11 121.63(13) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? N1 C1 C2 106.45(13) . . ? N1 C1 C4 121.76(13) . . ? C2 C1 C4 131.77(13) . . ? N2 C3 N3 122.23(12) . . ? N2 C3 C2 112.25(12) . . ? N3 C3 C2 125.52(12) . . ? C10 C11 C6 120.22(13) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C1 N1 N2 112.84(12) . . ? C1 N1 H1 123.6 . . ? N2 N1 H1 123.6 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 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 O2 N5 C8 C7 8.2(2) . . . . ? O3 N5 C8 C7 -171.24(13) . . . . ? O2 N5 C8 C9 -172.38(13) . . . . ? O3 N5 C8 C9 8.2(2) . . . . ? C7 C8 C9 C10 -0.2(2) . . . . ? N5 C8 C9 C10 -179.62(13) . . . . ? C9 C8 C7 C6 0.6(2) . . . . ? N5 C8 C7 C6 179.98(13) . . . . ? C3 N3 C5 O1 179.21(15) . . . . ? C3 N3 C5 N4 -0.7(2) . . . . ? C6 N4 C5 O1 -3.6(2) . . . . ? C6 N4 C5 N3 176.31(13) . . . . ? C5 N4 C6 C11 5.1(2) . . . . ? C5 N4 C6 C7 -174.82(14) . . . . ? C8 C7 C6 N4 179.50(12) . . . . ? C8 C7 C6 C11 -0.4(2) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C3 C2 C1 N1 -0.89(16) . . . . ? C3 C2 C1 C4 177.22(16) . . . . ? N1 N2 C3 N3 179.84(13) . . . . ? N1 N2 C3 C2 -0.34(17) . . . . ? C5 N3 C3 N2 -5.8(2) . . . . ? C5 N3 C3 C2 174.36(15) . . . . ? C1 C2 C3 N2 0.79(18) . . . . ? C1 C2 C3 N3 -179.40(14) . . . . ? C9 C10 C11 C6 0.5(2) . . . . ? N4 C6 C11 C10 -179.99(14) . . . . ? C7 C6 C11 C10 -0.1(2) . . . . ? C2 C1 N1 N2 0.76(18) . . . . ? C4 C1 N1 N2 -177.59(14) . . . . ? C3 N2 N1 C1 -0.27(17) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.346 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.063 # Attachment '- BF4 cocrystal.CIF' data_BF4cocrystal _database_code_depnum_ccdc_archive 'CCDC 783192' #TrackingRef '- BF4 cocrystal.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3.10H+)(BF4).3.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 B F4 N10 O6' _chemical_formula_weight 610.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 7.5596(4) _cell_length_b 12.6366(6) _cell_length_c 13.7797(6) _cell_angle_alpha 100.6610(10) _cell_angle_beta 94.926(2) _cell_angle_gamma 96.370(2) _cell_volume 1277.98(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SMART1000 _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 17616 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.00 _reflns_number_total 6149 _reflns_number_gt 3877 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker software' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _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^)+(0.0884P)^2^+0.6845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6149 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1747 _refine_ls_wR_factor_gt 0.1474 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 F1 F 0.3214(3) 0.05318(14) 0.90883(14) 0.0436(5) Uani 1 1 d . . . O1 O 0.4426(2) 0.39367(14) 0.75807(13) 0.0224(4) Uani 1 1 d . . . N1 N 0.7267(3) 0.44282(17) 1.02708(15) 0.0200(5) Uani 1 1 d . . . H1N H 0.7899 0.5065 1.0510 0.024 Uiso 0.50 1 calc PR . . C1 C 0.8112(4) 0.3668(2) 1.17317(18) 0.0224(5) Uani 1 1 d . . . H1A H 0.9404 0.3795 1.1691 0.034 Uiso 1 1 calc R . . H1B H 0.7823 0.2992 1.1970 0.034 Uiso 1 1 calc R . . H1C H 0.7755 0.4274 1.2193 0.034 Uiso 1 1 calc R . . B1 B 0.1790(5) -0.0102(2) 0.8472(2) 0.0297(7) Uani 1 1 d . . . F2 F 0.1571(3) 0.03332(15) 0.76165(13) 0.0441(5) Uani 1 1 d . . . O2 O 0.2244(3) 0.52015(16) 0.49347(15) 0.0397(6) Uani 1 1 d . . . N2 N 0.6262(3) 0.41364(16) 0.93753(15) 0.0191(4) Uani 1 1 d . . . H2N H 0.6133 0.4554 0.8936 0.023 Uiso 1 1 calc R . . C2 C 0.7131(3) 0.3580(2) 1.07267(18) 0.0183(5) Uani 1 1 d . . . F3 F 0.2076(3) -0.11659(13) 0.82240(16) 0.0476(5) Uani 1 1 d . . . O3 O 0.0570(3) 0.44167(17) 0.35990(14) 0.0371(5) Uani 1 1 d . . . N3 N 0.4390(3) 0.25629(17) 0.84506(15) 0.0196(5) Uani 1 1 d . . . H3N H 0.3930 0.1892 0.8450 0.024 Uiso 1 1 calc R . . C3 C 0.6032(3) 0.2726(2) 1.01168(18) 0.0192(5) Uani 1 1 d . . . H3 H 0.5708 0.2023 1.0249 0.023 Uiso 1 1 calc R . . F4 F 0.0227(2) -0.00317(13) 0.89483(13) 0.0392(5) Uani 1 1 d . . . O4 O -0.2167(3) -0.37838(14) 0.94439(13) 0.0252(4) Uani 1 1 d . . . N4 N 0.2953(3) 0.22364(17) 0.68903(15) 0.0230(5) Uani 1 1 d . . . H4N H 0.2714 0.1586 0.7027 0.028 Uiso 1 1 calc R . . C4 C 0.5498(3) 0.31081(19) 0.92712(18) 0.0178(5) Uani 1 1 d . . . O5 O -0.4687(3) 0.02224(16) 0.69842(17) 0.0396(5) Uani 1 1 d . . . N5 N 0.1408(3) 0.43970(19) 0.43937(16) 0.0268(5) Uani 1 1 d . . . C5 C 0.3943(3) 0.2993(2) 0.76217(18) 0.0193(5) Uani 1 1 d . . . O6 O -0.6424(3) -0.08423(18) 0.57873(16) 0.0430(6) Uani 1 1 d . . . N6 N 0.0484(3) -0.37823(18) 1.22540(16) 0.0250(5) Uani 1 1 d . . . H6N H 0.0405 -0.4365 1.2520 0.030 Uiso 0.50 1 calc PR . . C6 C 0.2261(3) 0.2360(2) 0.59411(18) 0.0214(5) Uani 1 1 d . . . N7 N -0.0380(3) -0.37422(18) 1.13511(16) 0.0237(5) Uani 1 1 d . . . H7N H -0.1094 -0.4261 1.0940 0.028 Uiso 1 1 calc R . . C7 C 0.2212(3) 0.3355(2) 0.56611(18) 0.0215(5) Uani 1 1 d . . . H7 H 0.2700 0.4015 0.6099 0.026 Uiso 1 1 calc R . . N8 N -0.0449(3) -0.23116(18) 1.04257(16) 0.0223(5) Uani 1 1 d . . . H8N H -0.0031 -0.1629 1.0443 0.027 Uiso 1 1 calc R . . C8 C 0.1414(4) 0.3348(2) 0.47076(19) 0.0218(5) Uani 1 1 d . . . N9 N -0.1911(3) -0.21317(18) 0.89746(16) 0.0240(5) Uani 1 1 d . . . H9N H -0.1335 -0.1469 0.9141 0.029 Uiso 1 1 calc R . . C9 C 0.0673(4) 0.2423(2) 0.4044(2) 0.0250(6) Uani 1 1 d . . . H9 H 0.0105 0.2459 0.3411 0.030 Uiso 1 1 calc R . . N10 N -0.5323(3) -0.06855(19) 0.65235(18) 0.0297(5) Uani 1 1 d . . . C10 C 0.0786(4) 0.1435(2) 0.4333(2) 0.0277(6) Uani 1 1 d . . . H10 H 0.0316 0.0778 0.3886 0.033 Uiso 1 1 calc R . . C11 C 0.1579(4) 0.1402(2) 0.5270(2) 0.0271(6) Uani 1 1 d . . . H11 H 0.1661 0.0721 0.5458 0.033 Uiso 1 1 calc R . . C12 C 0.2490(4) -0.2669(2) 1.3697(2) 0.0280(6) Uani 1 1 d . . . H12C H 0.1660 -0.2583 1.4206 0.042 Uiso 1 1 calc R . . H12A H 0.3364 -0.2015 1.3798 0.042 Uiso 1 1 calc R . . H12B H 0.3116 -0.3299 1.3746 0.042 Uiso 1 1 calc R . . C13 C 0.1469(4) -0.2837(2) 1.26926(19) 0.0233(6) Uani 1 1 d . . . C14 C 0.1270(4) -0.2131(2) 1.20535(19) 0.0226(5) Uani 1 1 d . . . H14 H 0.1800 -0.1398 1.2142 0.027 Uiso 1 1 calc R . . C15 C 0.0113(3) -0.2734(2) 1.12435(19) 0.0213(5) Uani 1 1 d . . . C16 C -0.1557(3) -0.2810(2) 0.96037(18) 0.0207(5) Uani 1 1 d . . . C17 C -0.3088(3) -0.2354(2) 0.80856(18) 0.0195(5) Uani 1 1 d . . . C18 C -0.3637(4) -0.1464(2) 0.77462(19) 0.0231(6) Uani 1 1 d . . . H18 H -0.3246 -0.0748 0.8107 0.028 Uiso 1 1 calc R . . C19 C -0.4760(4) -0.1638(2) 0.6876(2) 0.0247(6) Uani 1 1 d . . . C20 C -0.5387(4) -0.2671(2) 0.63323(19) 0.0248(6) Uani 1 1 d . . . H20 H -0.6175 -0.2773 0.5738 0.030 Uiso 1 1 calc R . . C21 C -0.4825(4) -0.3535(2) 0.6686(2) 0.0271(6) Uani 1 1 d . . . H21 H -0.5225 -0.4250 0.6324 0.033 Uiso 1 1 calc R . . C22 C -0.3694(4) -0.3398(2) 0.75531(19) 0.0254(6) Uani 1 1 d . . . H22 H -0.3331 -0.4011 0.7785 0.031 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 F1 0.0428(11) 0.0335(10) 0.0478(11) 0.0057(8) -0.0110(9) -0.0081(8) O1 0.0264(10) 0.0187(9) 0.0220(9) 0.0082(7) -0.0022(7) -0.0002(7) N1 0.0235(11) 0.0177(10) 0.0174(10) 0.0041(8) -0.0035(8) -0.0003(8) C1 0.0255(14) 0.0213(13) 0.0181(12) 0.0021(10) -0.0037(10) 0.0010(10) B1 0.0377(19) 0.0179(14) 0.0307(17) 0.0012(13) 0.0024(14) -0.0016(13) F2 0.0559(12) 0.0388(10) 0.0378(10) 0.0145(8) 0.0049(9) -0.0042(9) O2 0.0626(15) 0.0225(10) 0.0296(11) 0.0080(9) -0.0176(10) -0.0009(10) N2 0.0223(11) 0.0161(10) 0.0189(10) 0.0075(8) -0.0035(8) 0.0001(8) C2 0.0186(12) 0.0202(12) 0.0166(12) 0.0042(9) 0.0008(9) 0.0042(10) F3 0.0577(13) 0.0173(8) 0.0671(14) 0.0046(8) 0.0123(10) 0.0035(8) O3 0.0510(14) 0.0361(12) 0.0239(11) 0.0101(9) -0.0119(9) 0.0098(10) N3 0.0213(11) 0.0170(10) 0.0195(11) 0.0080(8) -0.0044(8) -0.0041(8) C3 0.0218(13) 0.0158(12) 0.0204(12) 0.0067(10) -0.0004(10) 0.0007(10) F4 0.0443(11) 0.0248(9) 0.0465(11) 0.0031(8) 0.0160(8) -0.0063(8) O4 0.0311(11) 0.0174(9) 0.0253(10) 0.0057(7) -0.0025(8) -0.0027(8) N4 0.0291(12) 0.0198(11) 0.0190(11) 0.0082(9) -0.0043(9) -0.0035(9) C4 0.0168(12) 0.0181(12) 0.0185(12) 0.0041(9) 0.0018(9) 0.0013(9) O5 0.0439(13) 0.0239(10) 0.0483(14) 0.0109(10) -0.0132(10) -0.0001(9) N5 0.0331(13) 0.0272(12) 0.0206(12) 0.0066(9) -0.0032(10) 0.0074(10) C5 0.0178(12) 0.0213(13) 0.0203(12) 0.0076(10) 0.0029(10) 0.0022(10) O6 0.0507(15) 0.0392(13) 0.0361(12) 0.0088(10) -0.0194(11) 0.0088(11) N6 0.0294(12) 0.0253(12) 0.0194(11) 0.0066(9) -0.0029(9) 0.0009(9) C6 0.0192(13) 0.0263(13) 0.0184(13) 0.0077(10) -0.0021(10) -0.0004(10) N7 0.0264(12) 0.0214(11) 0.0214(11) 0.0049(9) -0.0044(9) -0.0010(9) C7 0.0226(13) 0.0237(13) 0.0180(12) 0.0041(10) 0.0007(10) 0.0032(10) N8 0.0250(12) 0.0203(11) 0.0223(11) 0.0094(9) -0.0024(9) 0.0007(9) C8 0.0231(13) 0.0233(13) 0.0204(13) 0.0078(10) -0.0005(10) 0.0049(10) N9 0.0286(12) 0.0171(10) 0.0241(11) 0.0057(9) -0.0037(9) -0.0044(9) C9 0.0235(14) 0.0310(15) 0.0199(13) 0.0072(11) -0.0020(10) 0.0009(11) N10 0.0339(14) 0.0269(12) 0.0277(13) 0.0083(10) -0.0049(10) 0.0024(10) C10 0.0300(15) 0.0274(14) 0.0216(13) 0.0024(11) -0.0023(11) -0.0064(12) C11 0.0310(15) 0.0239(14) 0.0247(14) 0.0071(11) -0.0023(11) -0.0038(11) C12 0.0251(14) 0.0348(15) 0.0234(14) 0.0080(12) -0.0010(11) 0.0004(12) C13 0.0225(13) 0.0230(13) 0.0244(14) 0.0044(10) 0.0047(10) 0.0012(10) C14 0.0222(13) 0.0223(13) 0.0219(13) 0.0033(10) -0.0005(10) 0.0002(10) C15 0.0220(13) 0.0210(12) 0.0211(13) 0.0050(10) 0.0021(10) 0.0027(10) C16 0.0198(13) 0.0225(13) 0.0198(12) 0.0033(10) 0.0028(10) 0.0031(10) C17 0.0203(13) 0.0193(12) 0.0194(12) 0.0064(10) 0.0020(10) 0.0005(10) C18 0.0246(14) 0.0220(13) 0.0221(13) 0.0050(10) 0.0008(10) 0.0000(10) C19 0.0262(14) 0.0244(13) 0.0253(14) 0.0096(11) 0.0021(11) 0.0029(11) C20 0.0249(14) 0.0306(14) 0.0170(12) 0.0041(11) -0.0030(10) -0.0006(11) C21 0.0315(15) 0.0256(14) 0.0223(13) 0.0051(11) 0.0005(11) -0.0030(11) C22 0.0295(15) 0.0241(13) 0.0215(13) 0.0031(11) 0.0025(11) 0.0006(11) _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 F1 B1 1.386(4) . ? O1 C5 1.221(3) . ? N1 C2 1.338(3) . ? N1 N2 1.358(3) . ? N1 H1N 0.8800 . ? C1 C2 1.493(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? B1 F3 1.370(4) . ? B1 F2 1.396(4) . ? B1 F4 1.403(4) . ? O2 N5 1.219(3) . ? N2 C4 1.339(3) . ? N2 H2N 0.8800 . ? C2 C3 1.380(3) . ? O3 N5 1.223(3) . ? N3 C4 1.369(3) . ? N3 C5 1.385(3) . ? N3 H3N 0.8800 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? O4 C16 1.237(3) . ? N4 C5 1.358(3) . ? N4 C6 1.409(3) . ? N4 H4N 0.8800 . ? O5 N10 1.227(3) . ? N5 C8 1.469(3) . ? O6 N10 1.227(3) . ? N6 C13 1.343(3) . ? N6 N7 1.367(3) . ? N6 H6N 0.8800 . ? C6 C7 1.386(4) . ? C6 C11 1.397(4) . ? N7 C15 1.326(3) . ? N7 H7N 0.8800 . ? C7 C8 1.396(4) . ? C7 H7 0.9500 . ? N8 C16 1.356(3) . ? N8 C15 1.388(3) . ? N8 H8N 0.8800 . ? C8 C9 1.373(4) . ? N9 C16 1.358(3) . ? N9 C17 1.415(3) . ? N9 H9N 0.8800 . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? N10 C19 1.470(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.492(4) . ? C12 H12C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.375(4) . ? C14 C15 1.400(4) . ? C14 H14 0.9500 . ? C17 C18 1.387(4) . ? C17 C22 1.391(4) . ? C18 C19 1.376(4) . ? C18 H18 0.9500 . ? C19 C20 1.388(4) . ? C20 C21 1.370(4) . ? C20 H20 0.9500 . ? C21 C22 1.379(4) . ? C21 H21 0.9500 . ? C22 H22 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 N1 N2 108.20(19) . . ? C2 N1 H1N 125.9 . . ? N2 N1 H1N 125.9 . . ? 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 . . ? F3 B1 F1 112.1(3) . . ? F3 B1 F2 109.9(3) . . ? F1 B1 F2 107.4(2) . . ? F3 B1 F4 109.9(2) . . ? F1 B1 F4 109.1(2) . . ? F2 B1 F4 108.2(3) . . ? C4 N2 N1 108.8(2) . . ? C4 N2 H2N 125.6 . . ? N1 N2 H2N 125.6 . . ? N1 C2 C3 108.9(2) . . ? N1 C2 C1 119.9(2) . . ? C3 C2 C1 131.1(2) . . ? C4 N3 C5 124.6(2) . . ? C4 N3 H3N 117.7 . . ? C5 N3 H3N 117.7 . . ? C2 C3 C4 105.8(2) . . ? C2 C3 H3 127.1 . . ? C4 C3 H3 127.1 . . ? C5 N4 C6 128.3(2) . . ? C5 N4 H4N 115.8 . . ? C6 N4 H4N 115.8 . . ? N2 C4 N3 123.8(2) . . ? N2 C4 C3 108.3(2) . . ? N3 C4 C3 127.9(2) . . ? O2 N5 O3 123.3(2) . . ? O2 N5 C8 118.4(2) . . ? O3 N5 C8 118.2(2) . . ? O1 C5 N4 126.1(2) . . ? O1 C5 N3 122.3(2) . . ? N4 C5 N3 111.6(2) . . ? C13 N6 N7 112.8(2) . . ? C13 N6 H6N 123.6 . . ? N7 N6 H6N 123.6 . . ? C7 C6 C11 120.1(2) . . ? C7 C6 N4 123.9(2) . . ? C11 C6 N4 116.1(2) . . ? C15 N7 N6 103.5(2) . . ? C15 N7 H7N 128.3 . . ? N6 N7 H7N 128.3 . . ? C6 C7 C8 117.2(2) . . ? C6 C7 H7 121.4 . . ? C8 C7 H7 121.4 . . ? C16 N8 C15 128.6(2) . . ? C16 N8 H8N 115.7 . . ? C15 N8 H8N 115.7 . . ? C9 C8 C7 124.1(2) . . ? C9 C8 N5 118.4(2) . . ? C7 C8 N5 117.5(2) . . ? C16 N9 C17 128.3(2) . . ? C16 N9 H9N 115.9 . . ? C17 N9 H9N 115.9 . . ? C8 C9 C10 117.6(2) . . ? C8 C9 H9 121.2 . . ? C10 C9 H9 121.2 . . ? O5 N10 O6 123.4(2) . . ? O5 N10 C19 118.6(2) . . ? O6 N10 C19 118.0(2) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C6 120.7(3) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? C13 C12 H12C 109.5 . . ? C13 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N6 C13 C14 106.6(2) . . ? N6 C13 C12 122.8(2) . . ? C14 C13 C12 130.6(2) . . ? C13 C14 C15 104.7(2) . . ? C13 C14 H14 127.6 . . ? C15 C14 H14 127.6 . . ? N7 C15 N8 124.3(2) . . ? N7 C15 C14 112.4(2) . . ? N8 C15 C14 123.2(2) . . ? O4 C16 N8 123.3(2) . . ? O4 C16 N9 123.8(2) . . ? N8 C16 N9 112.9(2) . . ? C18 C17 C22 119.8(2) . . ? C18 C17 N9 116.5(2) . . ? C22 C17 N9 123.7(2) . . ? C19 C18 C17 118.6(2) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 122.6(3) . . ? C18 C19 N10 118.0(2) . . ? C20 C19 N10 119.4(2) . . ? C21 C20 C19 117.4(2) . . ? C21 C20 H20 121.3 . . ? C19 C20 H20 121.3 . . ? C20 C21 C22 121.8(3) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C17 119.6(3) . . ? C21 C22 H22 120.2 . . ? C17 C22 H22 120.2 . . ? 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 C2 N1 N2 C4 0.0(3) . . . . ? N2 N1 C2 C3 0.3(3) . . . . ? N2 N1 C2 C1 179.7(2) . . . . ? N1 C2 C3 C4 -0.5(3) . . . . ? C1 C2 C3 C4 -179.8(3) . . . . ? N1 N2 C4 N3 179.8(2) . . . . ? N1 N2 C4 C3 -0.3(3) . . . . ? C5 N3 C4 N2 1.1(4) . . . . ? C5 N3 C4 C3 -178.7(3) . . . . ? C2 C3 C4 N2 0.5(3) . . . . ? C2 C3 C4 N3 -179.6(2) . . . . ? C6 N4 C5 O1 -0.4(4) . . . . ? C6 N4 C5 N3 -179.5(2) . . . . ? C4 N3 C5 O1 -4.6(4) . . . . ? C4 N3 C5 N4 174.5(2) . . . . ? C5 N4 C6 C7 -12.4(4) . . . . ? C5 N4 C6 C11 168.4(3) . . . . ? C13 N6 N7 C15 0.3(3) . . . . ? C11 C6 C7 C8 1.9(4) . . . . ? N4 C6 C7 C8 -177.3(2) . . . . ? C6 C7 C8 C9 0.6(4) . . . . ? C6 C7 C8 N5 -178.1(2) . . . . ? O2 N5 C8 C9 -171.6(3) . . . . ? O3 N5 C8 C9 8.0(4) . . . . ? O2 N5 C8 C7 7.1(4) . . . . ? O3 N5 C8 C7 -173.3(2) . . . . ? C7 C8 C9 C10 -2.3(4) . . . . ? N5 C8 C9 C10 176.3(2) . . . . ? C8 C9 C10 C11 1.7(4) . . . . ? C9 C10 C11 C6 0.7(4) . . . . ? C7 C6 C11 C10 -2.5(4) . . . . ? N4 C6 C11 C10 176.7(3) . . . . ? N7 N6 C13 C14 -0.5(3) . . . . ? N7 N6 C13 C12 178.0(2) . . . . ? N6 C13 C14 C15 0.5(3) . . . . ? C12 C13 C14 C15 -177.9(3) . . . . ? N6 N7 C15 N8 -179.7(2) . . . . ? N6 N7 C15 C14 0.0(3) . . . . ? C16 N8 C15 N7 -0.2(4) . . . . ? C16 N8 C15 C14 -180.0(3) . . . . ? C13 C14 C15 N7 -0.3(3) . . . . ? C13 C14 C15 N8 179.4(2) . . . . ? C15 N8 C16 O4 -4.4(4) . . . . ? C15 N8 C16 N9 176.1(2) . . . . ? C17 N9 C16 O4 4.8(4) . . . . ? C17 N9 C16 N8 -175.7(2) . . . . ? C16 N9 C17 C18 160.5(3) . . . . ? C16 N9 C17 C22 -19.7(4) . . . . ? C22 C17 C18 C19 -0.8(4) . . . . ? N9 C17 C18 C19 179.0(2) . . . . ? C17 C18 C19 C20 1.0(4) . . . . ? C17 C18 C19 N10 -179.7(2) . . . . ? O5 N10 C19 C18 4.3(4) . . . . ? O6 N10 C19 C18 -174.8(3) . . . . ? O5 N10 C19 C20 -176.4(3) . . . . ? O6 N10 C19 C20 4.4(4) . . . . ? C18 C19 C20 C21 -0.9(4) . . . . ? N10 C19 C20 C21 179.8(3) . . . . ? C19 C20 C21 C22 0.6(4) . . . . ? C20 C21 C22 C17 -0.5(4) . . . . ? C18 C17 C22 C21 0.6(4) . . . . ? N9 C17 C22 C21 -179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.595 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.075 # Attachment '- BF4 salt.CIF' data_z:\xraydata\gareth\09srv289\work\srv289m _database_code_depnum_ccdc_archive 'CCDC 783193' #TrackingRef '- BF4 salt.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3.10H+)(BF4).H2O ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 B F4 N5 O4' _chemical_formula_weight 367.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7509(4) _cell_length_b 8.2203(5) _cell_length_c 13.2848(7) _cell_angle_alpha 94.481(2) _cell_angle_beta 104.643(2) _cell_angle_gamma 110.579(2) _cell_volume 753.54(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9541 _exptl_absorpt_correction_T_max 0.9804 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\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 12989 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4594 _reflns_number_gt 2963 _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^)+(0.0622P)^2^+0.3504P] 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 4594 _refine_ls_number_parameters 235 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 F1 F 0.57932(17) 0.25215(15) 0.28143(10) 0.0350(3) Uani 1 1 d . . . O1 O 0.13502(19) 0.69185(17) 0.29029(11) 0.0271(3) Uani 1 1 d . . . N1 N 0.0944(2) 0.8428(2) 0.57073(12) 0.0253(3) Uani 1 1 d . . . H1N H 0.0197 0.7634 0.5983 0.030 Uiso 1 1 calc R . . C1 C 0.2096(3) 1.0762(3) 0.72665(15) 0.0292(4) Uani 1 1 d . . . H1A H 0.1032 0.9911 0.7457 0.044 Uiso 1 1 calc R . . H1B H 0.1957 1.1903 0.7287 0.044 Uiso 1 1 calc R . . H1C H 0.3329 1.0908 0.7771 0.044 Uiso 1 1 calc R . . B1 B 0.6336(3) 0.4083(3) 0.35281(17) 0.0264(4) Uani 1 1 d . . . H1W H 0.151(5) 0.483(2) 0.329(3) 0.086(11) Uiso 1 1 d D . . F2 F 0.83179(16) 0.48046(15) 0.39809(11) 0.0368(3) Uani 1 1 d . . . O2 O 0.2330(3) 0.2611(2) 0.10864(12) 0.0391(4) Uani 1 1 d . . . N2 N 0.1152(2) 0.8143(2) 0.47385(12) 0.0247(3) Uani 1 1 d . . . H2N H 0.0569 0.7138 0.4283 0.030 Uiso 1 1 calc R . . C2 C 0.2048(3) 1.0100(2) 0.61820(15) 0.0249(4) Uani 1 1 d . . . H2W H 0.2879(10) 0.406(5) 0.377(3) 0.085(11) Uiso 1 1 d D . . F3 F 0.5431(2) 0.3634(2) 0.43119(11) 0.0499(4) Uani 1 1 d . . . O3 O 0.2316(3) 0.2279(2) -0.05349(13) 0.0540(5) Uani 1 1 d . . . N3 N 0.2873(2) 0.9835(2) 0.36593(12) 0.0247(3) Uani 1 1 d . . . H3N H 0.3565 1.0899 0.3583 0.030 Uiso 1 1 calc R . . C3 C 0.3007(3) 1.0918(2) 0.54923(15) 0.0256(4) Uani 1 1 d . . . H3 H 0.3901 1.2106 0.5615 0.031 Uiso 1 1 calc R . . F4 F 0.5740(2) 0.52818(17) 0.30346(12) 0.0505(4) Uani 1 1 d . . . O4 O 0.1532(2) 0.3739(2) 0.34644(13) 0.0352(4) Uani 1 1 d D . . N4 N 0.2936(2) 0.8905(2) 0.20006(13) 0.0264(3) Uani 1 1 d . . . H4N H 0.3533 1.0041 0.2018 0.032 Uiso 1 1 calc R . . C4 C 0.2393(2) 0.9644(2) 0.45861(14) 0.0224(4) Uani 1 1 d . . . N5 N 0.2372(2) 0.3168(2) 0.02615(13) 0.0290(4) Uani 1 1 d . . . C5 C 0.2317(3) 0.8427(2) 0.28421(15) 0.0236(4) Uani 1 1 d . . . C6 C 0.2696(3) 0.7713(2) 0.10931(15) 0.0236(4) Uani 1 1 d . . . C7 C 0.2627(3) 0.6006(2) 0.11408(15) 0.0240(4) Uani 1 1 d . . . H7 H 0.2678 0.5558 0.1781 0.029 Uiso 1 1 calc R . . C8 C 0.2483(3) 0.4987(2) 0.02212(15) 0.0247(4) Uani 1 1 d . . . C9 C 0.2445(3) 0.5575(3) -0.07241(16) 0.0319(4) Uani 1 1 d . . . H9 H 0.2361 0.4837 -0.1336 0.038 Uiso 1 1 calc R . . C10 C 0.2535(3) 0.7289(3) -0.07485(17) 0.0360(5) Uani 1 1 d . . . H10 H 0.2515 0.7737 -0.1387 0.043 Uiso 1 1 calc R . . C11 C 0.2653(3) 0.8355(3) 0.01504(16) 0.0300(4) Uani 1 1 d . . . H11 H 0.2705 0.9522 0.0123 0.036 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 F1 0.0355(6) 0.0229(6) 0.0398(7) -0.0021(5) 0.0078(5) 0.0075(5) O1 0.0307(7) 0.0183(6) 0.0301(7) 0.0026(5) 0.0110(6) 0.0059(5) N1 0.0267(8) 0.0230(7) 0.0263(8) 0.0038(6) 0.0090(6) 0.0093(6) C1 0.0308(10) 0.0284(9) 0.0264(9) 0.0013(7) 0.0067(8) 0.0111(8) B1 0.0251(10) 0.0198(9) 0.0298(11) 0.0012(8) 0.0065(8) 0.0051(8) F2 0.0240(6) 0.0245(6) 0.0521(8) -0.0016(5) 0.0075(5) 0.0026(5) O2 0.0618(10) 0.0279(7) 0.0307(8) 0.0065(6) 0.0136(7) 0.0210(7) N2 0.0255(7) 0.0202(7) 0.0267(8) 0.0004(6) 0.0084(6) 0.0073(6) C2 0.0234(8) 0.0230(8) 0.0268(9) 0.0002(7) 0.0040(7) 0.0107(7) F3 0.0438(8) 0.0525(9) 0.0452(8) 0.0021(6) 0.0257(7) 0.0017(7) O3 0.1021(16) 0.0347(9) 0.0372(9) 0.0020(7) 0.0273(10) 0.0367(10) N3 0.0266(7) 0.0177(7) 0.0274(8) 0.0008(6) 0.0101(6) 0.0050(6) C3 0.0233(8) 0.0209(8) 0.0282(9) -0.0011(7) 0.0049(7) 0.0064(7) F4 0.0569(9) 0.0281(7) 0.0548(9) 0.0012(6) -0.0067(7) 0.0204(6) O4 0.0351(8) 0.0294(8) 0.0458(9) 0.0100(7) 0.0195(7) 0.0124(6) N4 0.0314(8) 0.0174(7) 0.0292(8) 0.0016(6) 0.0132(7) 0.0057(6) C4 0.0210(8) 0.0197(8) 0.0260(9) 0.0012(7) 0.0064(7) 0.0084(7) N5 0.0343(9) 0.0242(8) 0.0275(8) -0.0002(6) 0.0074(7) 0.0122(7) C5 0.0217(8) 0.0201(8) 0.0284(9) 0.0015(7) 0.0064(7) 0.0087(7) C6 0.0218(8) 0.0205(8) 0.0264(9) -0.0007(7) 0.0079(7) 0.0062(7) C7 0.0241(8) 0.0217(8) 0.0245(9) 0.0024(7) 0.0059(7) 0.0080(7) C8 0.0252(9) 0.0203(8) 0.0265(9) 0.0012(7) 0.0058(7) 0.0084(7) C9 0.0416(11) 0.0299(10) 0.0254(9) 0.0016(8) 0.0110(8) 0.0151(9) C10 0.0502(13) 0.0321(10) 0.0285(10) 0.0085(8) 0.0138(9) 0.0169(10) C11 0.0380(10) 0.0222(9) 0.0318(10) 0.0065(7) 0.0119(8) 0.0128(8) _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 F1 B1 1.397(2) . ? O1 C5 1.224(2) . ? N1 C2 1.336(2) . ? N1 N2 1.350(2) . ? N1 H1N 0.8800 . ? C1 C2 1.486(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? B1 F4 1.372(3) . ? B1 F2 1.382(2) . ? B1 F3 1.400(3) . ? O2 N5 1.224(2) . ? N2 C4 1.338(2) . ? N2 H2N 0.8800 . ? C2 C3 1.391(3) . ? O3 N5 1.220(2) . ? N3 C4 1.378(2) . ? N3 C5 1.386(2) . ? N3 H3N 0.8800 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? O4 H1W 0.949(2) . ? O4 H2W 0.950(2) . ? N4 C5 1.357(2) . ? N4 C6 1.422(2) . ? N4 H4N 0.8800 . ? N5 C8 1.473(2) . ? C6 C7 1.393(3) . ? C6 C11 1.393(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.378(3) . ? C9 C10 1.389(3) . ? C9 H9 0.9500 . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 H11 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 N1 N2 109.45(16) . . ? C2 N1 H1N 125.3 . . ? N2 N1 H1N 125.3 . . ? 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 . . ? F4 B1 F2 109.91(16) . . ? F4 B1 F1 110.93(17) . . ? F2 B1 F1 110.03(16) . . ? F4 B1 F3 109.23(18) . . ? F2 B1 F3 109.72(17) . . ? F1 B1 F3 106.97(16) . . ? C4 N2 N1 108.66(15) . . ? C4 N2 H2N 125.7 . . ? N1 N2 H2N 125.7 . . ? N1 C2 C3 107.73(16) . . ? N1 C2 C1 120.50(18) . . ? C3 C2 C1 131.77(17) . . ? C4 N3 C5 122.98(16) . . ? C4 N3 H3N 118.5 . . ? C5 N3 H3N 118.5 . . ? C2 C3 C4 106.07(16) . . ? C2 C3 H3 127.0 . . ? C4 C3 H3 127.0 . . ? H1W O4 H2W 101(3) . . ? C5 N4 C6 125.10(16) . . ? C5 N4 H4N 117.4 . . ? C6 N4 H4N 117.4 . . ? N2 C4 N3 123.78(16) . . ? N2 C4 C3 108.08(16) . . ? N3 C4 C3 128.10(17) . . ? O3 N5 O2 122.89(17) . . ? O3 N5 C8 118.27(17) . . ? O2 N5 C8 118.83(16) . . ? O1 C5 N4 125.17(17) . . ? O1 C5 N3 121.37(17) . . ? N4 C5 N3 113.46(16) . . ? C7 C6 C11 120.34(17) . . ? C7 C6 N4 122.27(17) . . ? C11 C6 N4 117.26(16) . . ? C8 C7 C6 117.48(17) . . ? C8 C7 H7 121.3 . . ? C6 C7 H7 121.3 . . ? C9 C8 C7 123.89(17) . . ? C9 C8 N5 118.37(17) . . ? C7 C8 N5 117.74(17) . . ? C8 C9 C10 117.51(18) . . ? C8 C9 H9 121.2 . . ? C10 C9 H9 121.2 . . ? C11 C10 C9 120.74(19) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C6 120.02(18) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? 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 C2 N1 N2 C4 -0.2(2) . . . . ? N2 N1 C2 C3 -0.3(2) . . . . ? N2 N1 C2 C1 -179.68(16) . . . . ? N1 C2 C3 C4 0.6(2) . . . . ? C1 C2 C3 C4 179.94(19) . . . . ? N1 N2 C4 N3 -177.35(16) . . . . ? N1 N2 C4 C3 0.6(2) . . . . ? C5 N3 C4 N2 -8.8(3) . . . . ? C5 N3 C4 C3 173.64(17) . . . . ? C2 C3 C4 N2 -0.8(2) . . . . ? C2 C3 C4 N3 177.08(17) . . . . ? C6 N4 C5 O1 -5.4(3) . . . . ? C6 N4 C5 N3 175.00(16) . . . . ? C4 N3 C5 O1 0.2(3) . . . . ? C4 N3 C5 N4 179.80(16) . . . . ? C5 N4 C6 C7 -30.1(3) . . . . ? C5 N4 C6 C11 153.96(18) . . . . ? C11 C6 C7 C8 -1.1(3) . . . . ? N4 C6 C7 C8 -176.95(17) . . . . ? C6 C7 C8 C9 1.4(3) . . . . ? C6 C7 C8 N5 -178.87(16) . . . . ? O3 N5 C8 C9 2.4(3) . . . . ? O2 N5 C8 C9 -177.24(18) . . . . ? O3 N5 C8 C7 -177.36(19) . . . . ? O2 N5 C8 C7 3.0(3) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? N5 C8 C9 C10 179.48(18) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C6 0.4(3) . . . . ? C7 C6 C11 C10 0.2(3) . . . . ? N4 C6 C11 C10 176.27(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.444 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.078 # Attachment '- BOC precursor.CIF' data_z:\xraydata\gareth\09srv105\work\9srv105m _database_code_depnum_ccdc_archive 'CCDC 783194' #TrackingRef '- BOC precursor.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H15 N3 O2' _chemical_formula_sum 'C9 H15 N3 O2' _chemical_formula_weight 197.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.8180(3) _cell_length_b 9.6472(3) _cell_length_c 11.6088(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.9080(10) _cell_angle_gamma 90.00 _cell_volume 1052.01(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2227 _cell_measurement_theta_min 2.796 _cell_measurement_theta_max 30.222 _exptl_crystal_description 'block needles' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7998 _exptl_absorpt_correction_T_max 0.9884 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Smart 6K' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9734 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 30.51 _reflns_number_total 3201 _reflns_number_gt 2225 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _computing_publication_material X-Seed _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^)+(0.0664P)^2^+0.3504P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3201 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1448 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N1 N 0.16508(13) 1.22574(12) 0.19920(11) 0.0216(3) Uani 1 1 d . . . N2 N 0.24337(13) 1.14713(12) 0.29672(10) 0.0192(2) Uani 1 1 d . . . C3 C 0.22542(15) 1.19463(14) 0.40440(12) 0.0210(3) Uani 1 1 d . . . C4 C 0.13254(16) 1.30418(15) 0.37434(13) 0.0237(3) Uani 1 1 d . . . H4 H 0.0969 1.3585 0.4274 0.028 Uiso 1 1 calc R . . C5 C 0.10097(16) 1.31942(15) 0.24864(14) 0.0235(3) Uani 1 1 d . . . N6 N 0.28750(15) 1.13476(15) 0.51216(11) 0.0293(3) Uani 1 1 d . . . H6B H 0.2698 1.1664 0.5774 0.035 Uiso 1 1 calc R . . H6A H 0.3456 1.0641 0.5170 0.035 Uiso 1 1 calc R . . C7 C 0.00971(19) 1.42772(18) 0.17157(16) 0.0352(4) Uani 1 1 d . . . H7B H 0.0068 1.4128 0.0874 0.053 Uiso 0.50 1 calc PR . . H7D H 0.0494 1.5196 0.1976 0.053 Uiso 0.50 1 calc PR . . H7F H -0.0870 1.4218 0.1792 0.053 Uiso 0.50 1 calc PR . . H7E H -0.0273 1.4900 0.2220 0.053 Uiso 0.50 1 calc PR . . H7A H -0.0699 1.3832 0.1119 0.053 Uiso 0.50 1 calc PR . . H7C H 0.0664 1.4810 0.1302 0.053 Uiso 0.50 1 calc PR . . C8 C 0.31452(15) 1.02700(14) 0.28116(12) 0.0205(3) Uani 1 1 d . . . O9 O 0.40106(12) 0.97202(12) 0.36478(10) 0.0293(3) Uani 1 1 d . . . O10 O 0.27174(11) 0.98575(10) 0.16786(9) 0.0227(2) Uani 1 1 d . . . C11 C 0.33688(18) 0.86238(15) 0.12808(13) 0.0270(3) Uani 1 1 d . . . C12 C 0.3144(3) 0.73493(19) 0.19624(19) 0.0534(6) Uani 1 1 d . . . H12A H 0.3675 0.7449 0.2815 0.080 Uiso 1 1 calc R . . H12B H 0.3485 0.6529 0.1631 0.080 Uiso 1 1 calc R . . H12C H 0.2128 0.7245 0.1882 0.080 Uiso 1 1 calc R . . C13 C 0.25325(19) 0.85228(18) -0.00393(15) 0.0335(4) Uani 1 1 d . . . H13C H 0.2702 0.9354 -0.0463 0.050 Uiso 1 1 calc R . . H13A H 0.1515 0.8447 -0.0115 0.050 Uiso 1 1 calc R . . H13B H 0.2841 0.7702 -0.0393 0.050 Uiso 1 1 calc R . . C14 C 0.49193(19) 0.8938(2) 0.14252(16) 0.0413(5) Uani 1 1 d . . . H14A H 0.4990 0.9764 0.0954 0.062 Uiso 1 1 calc R . . H14B H 0.5358 0.8148 0.1138 0.062 Uiso 1 1 calc R . . H14C H 0.5415 0.9107 0.2277 0.062 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 N1 0.0249(6) 0.0206(5) 0.0203(6) 0.0029(4) 0.0083(5) 0.0033(5) N2 0.0222(6) 0.0198(5) 0.0172(5) -0.0003(4) 0.0080(4) 0.0009(4) C3 0.0221(7) 0.0229(6) 0.0201(7) -0.0035(5) 0.0097(5) -0.0040(5) C4 0.0261(7) 0.0226(6) 0.0258(7) -0.0048(5) 0.0131(6) -0.0018(5) C5 0.0234(7) 0.0206(6) 0.0284(7) 0.0001(6) 0.0107(6) -0.0002(5) N6 0.0332(7) 0.0384(7) 0.0175(6) -0.0022(5) 0.0093(5) 0.0061(6) C7 0.0386(9) 0.0302(8) 0.0399(9) 0.0088(7) 0.0164(7) 0.0133(7) C8 0.0227(7) 0.0214(6) 0.0197(6) 0.0000(5) 0.0099(5) -0.0002(5) O9 0.0329(6) 0.0328(6) 0.0214(5) 0.0027(4) 0.0068(4) 0.0111(5) O10 0.0268(5) 0.0224(5) 0.0199(5) -0.0032(4) 0.0082(4) 0.0052(4) C11 0.0398(9) 0.0229(7) 0.0228(7) -0.0003(6) 0.0162(6) 0.0086(6) C12 0.1079(19) 0.0239(8) 0.0416(11) 0.0022(8) 0.0425(12) 0.0076(10) C13 0.0420(9) 0.0329(8) 0.0280(8) -0.0091(7) 0.0139(7) 0.0035(7) C14 0.0339(9) 0.0640(12) 0.0287(9) 0.0016(8) 0.0135(7) 0.0198(9) _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 N1 C5 1.3238(18) . ? N1 N2 1.3934(16) . ? N2 C3 1.3899(17) . ? N2 C8 1.3918(18) . ? C3 N6 1.3514(19) . ? C3 C4 1.373(2) . ? C4 C5 1.409(2) . ? C4 H4 0.9500 . ? C5 C7 1.493(2) . ? N6 H6B 0.8800 . ? N6 H6A 0.8800 . ? C7 H7B 0.9800 . ? C7 H7D 0.9800 . ? C7 H7F 0.9800 . ? C7 H7E 0.9800 . ? C7 H7A 0.9800 . ? C7 H7C 0.9800 . ? C8 O9 1.2107(17) . ? C8 O10 1.3204(17) . ? O10 C11 1.4868(17) . ? C11 C12 1.512(2) . ? C11 C14 1.513(2) . ? C11 C13 1.517(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C5 N1 N2 103.82(11) . . ? C3 N2 C8 126.22(12) . . ? C3 N2 N1 111.53(11) . . ? C8 N2 N1 121.79(11) . . ? N6 C3 C4 130.66(13) . . ? N6 C3 N2 123.41(13) . . ? C4 C3 N2 105.89(12) . . ? C3 C4 C5 105.87(12) . . ? C3 C4 H4 127.1 . . ? C5 C4 H4 127.1 . . ? N1 C5 C4 112.88(13) . . ? N1 C5 C7 119.75(14) . . ? C4 C5 C7 127.36(14) . . ? C3 N6 H6B 120.0 . . ? C3 N6 H6A 120.0 . . ? H6B N6 H6A 120.0 . . ? C5 C7 H7B 109.5 . . ? C5 C7 H7D 109.5 . . ? H7B C7 H7D 109.5 . . ? C5 C7 H7F 109.5 . . ? H7B C7 H7F 109.5 . . ? H7D C7 H7F 109.5 . . ? C5 C7 H7E 109.5 . . ? H7B C7 H7E 141.1 . . ? H7D C7 H7E 56.3 . . ? H7F C7 H7E 56.3 . . ? C5 C7 H7A 109.5 . . ? H7B C7 H7A 56.3 . . ? H7D C7 H7A 141.1 . . ? H7F C7 H7A 56.3 . . ? H7E C7 H7A 109.5 . . ? C5 C7 H7C 109.5 . . ? H7B C7 H7C 56.3 . . ? H7D C7 H7C 56.3 . . ? H7F C7 H7C 141.1 . . ? H7E C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? O9 C8 O10 127.77(13) . . ? O9 C8 N2 121.49(13) . . ? O10 C8 N2 110.73(12) . . ? C8 O10 C11 120.64(11) . . ? O10 C11 C12 110.31(12) . . ? O10 C11 C14 108.35(13) . . ? C12 C11 C14 113.58(17) . . ? O10 C11 C13 102.12(12) . . ? C12 C11 C13 110.97(15) . . ? C14 C11 C13 110.88(13) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13C 109.5 . . ? C11 C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C5 N1 N2 C3 0.00(15) . . . . ? C5 N1 N2 C8 172.76(12) . . . . ? C8 N2 C3 N6 6.3(2) . . . . ? N1 N2 C3 N6 178.66(13) . . . . ? C8 N2 C3 C4 -171.57(13) . . . . ? N1 N2 C3 C4 0.81(16) . . . . ? N6 C3 C4 C5 -178.87(15) . . . . ? N2 C3 C4 C5 -1.23(15) . . . . ? N2 N1 C5 C4 -0.82(16) . . . . ? N2 N1 C5 C7 177.80(13) . . . . ? C3 C4 C5 N1 1.34(17) . . . . ? C3 C4 C5 C7 -177.15(15) . . . . ? C3 N2 C8 O9 -20.9(2) . . . . ? N1 N2 C8 O9 167.41(13) . . . . ? C3 N2 C8 O10 157.95(13) . . . . ? N1 N2 C8 O10 -13.70(18) . . . . ? O9 C8 O10 C11 -3.7(2) . . . . ? N2 C8 O10 C11 177.55(12) . . . . ? C8 O10 C11 C12 60.2(2) . . . . ? C8 O10 C11 C14 -64.65(16) . . . . ? C8 O10 C11 C13 178.27(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.366 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.055 # Attachment '- Cl salt.CIF' data_Clsalt _database_code_depnum_ccdc_archive 'CCDC 783195' #TrackingRef '- Cl salt.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2(3.10H+) 2Cl MeOH H2O ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 Cl2 N10 O8' _chemical_formula_weight 643.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 7.557(8) _cell_length_b 14.027(16) _cell_length_c 15.689(17) _cell_angle_alpha 70.74(2) _cell_angle_beta 77.71(2) _cell_angle_gamma 87.03(2) _cell_volume 1534(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9349 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SMART1000 _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 15248 _diffrn_reflns_av_R_equivalents 0.2267 _diffrn_reflns_av_sigmaI/netI 0.2405 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5366 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker software' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5366 _refine_ls_number_parameters 383 _refine_ls_number_restraints 280 _refine_ls_R_factor_all 0.3683 _refine_ls_R_factor_gt 0.2848 _refine_ls_wR_factor_ref 0.6243 _refine_ls_wR_factor_gt 0.5981 _refine_ls_goodness_of_fit_ref 1.812 _refine_ls_restrained_S_all 1.784 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.4643(8) 0.9115(4) 0.2665(4) 0.0492(16) Uani 1 1 d U . . O1 O 0.8417(17) 0.9912(10) -0.0564(9) 0.037(3) Uani 1 1 d U . . N1 N 0.638(2) 1.2712(10) -0.1342(12) 0.050(5) Uani 1 1 d DU . . H1N H 0.6641 1.3107 -0.1921 0.060 Uiso 1 1 calc R . . C1 C 0.445(4) 1.398(2) -0.058(2) 0.090(10) Uani 1 1 d U . . H1B H 0.3688 1.3888 0.0034 0.135 Uiso 1 1 calc R . . H1C H 0.3701 1.4197 -0.1044 0.135 Uiso 1 1 calc R . . H1A H 0.5399 1.4485 -0.0711 0.135 Uiso 1 1 calc R . . O2 O 1.152(2) 0.7518(13) -0.1462(11) 0.060(4) Uani 1 1 d U . . N2 N 0.685(2) 1.1750(10) -0.0949(8) 0.042(4) Uani 1 1 d DU . . H2N H 0.7501 1.1390 -0.1261 0.051 Uiso 1 1 calc R . . C2 C 0.539(5) 1.2892(18) -0.0596(11) 0.105(11) Uani 1 1 d DU . . O3 O 1.200(2) 0.5942(12) -0.0661(11) 0.055(4) Uani 1 1 d U . . N3 N 0.646(2) 1.0394(11) 0.0534(10) 0.028(4) Uani 1 1 d U . . H3N H 0.5854 1.0209 0.1111 0.034 Uiso 1 1 calc R . . C3 C 0.520(2) 1.2134(11) 0.0255(12) 0.032(4) Uani 1 1 d DU . . H3 H 0.4574 1.2122 0.0852 0.038 Uiso 1 1 calc R . . O4 O 0.1762(17) 0.9924(9) 0.5501(9) 0.036(3) Uani 1 1 d U . . N4 N 0.752(2) 0.8795(11) 0.0941(11) 0.032(4) Uani 1 1 d U . . H4N H 0.6801 0.8771 0.1469 0.038 Uiso 1 1 calc R . . C4 C 0.622(2) 1.1401(10) -0.0034(9) 0.025(4) Uani 1 1 d DU . . O5 O -0.200(2) 0.7892(12) 0.7915(10) 0.051(4) Uani 1 1 d U . . N5 N 1.134(2) 0.6804(13) -0.0774(12) 0.038(4) Uani 1 1 d U . . C5 C 0.758(2) 0.9665(13) 0.0250(12) 0.026(4) Uani 1 1 d U . . O6 O -0.239(3) 0.6280(15) 0.8336(14) 0.081(6) Uani 1 1 d U . . N6 N 0.439(2) 1.2589(9) 0.4432(9) 0.041(4) Uani 1 1 d DU . . H6N H 0.4284 1.2987 0.4770 0.049 Uiso 1 1 calc R . . C6 C 0.851(2) 0.7872(11) 0.0921(8) 0.028(4) Uani 1 1 d DU . . N7 N 0.3630(19) 1.1656(9) 0.4712(9) 0.029(4) Uani 1 1 d DU . . H7N H 0.2909 1.1365 0.5249 0.035 Uiso 1 1 calc R . . C7 C 0.943(2) 0.7808(10) 0.0075(9) 0.027(4) Uani 1 1 d DU . . H7 H 0.9499 0.8349 -0.0488 0.032 Uiso 1 1 calc R . . N8 N 0.361(2) 1.0339(10) 0.4072(10) 0.027(3) Uani 1 1 d U . . H8N H 0.4050 1.0131 0.3599 0.032 Uiso 1 1 calc R . . C8 C 1.024(2) 0.6884(10) 0.0124(11) 0.034(5) Uani 1 1 d DU . . N9 N 0.2192(19) 0.8803(10) 0.4736(10) 0.024(3) Uani 1 1 d U . . H9N H 0.2857 0.8690 0.4247 0.028 Uiso 1 1 calc R . . C9 C 1.025(3) 0.6084(13) 0.0933(9) 0.048(6) Uani 1 1 d DU . . H9 H 1.0869 0.5481 0.0921 0.057 Uiso 1 1 calc R . . N10 N -0.182(2) 0.7111(12) 0.7782(11) 0.034(4) Uani 1 1 d U . . C10 C 0.931(3) 0.6192(13) 0.1759(12) 0.046(5) Uani 1 1 d DU . . H10 H 0.9282 0.5660 0.2325 0.056 Uiso 1 1 calc R . . C11 C 0.842(2) 0.7085(10) 0.1749(10) 0.035(5) Uani 1 1 d DU . . H11 H 0.7740 0.7159 0.2308 0.042 Uiso 1 1 calc R . . C12 C 0.628(3) 1.3848(15) 0.3068(14) 0.039(5) Uani 1 1 d U . . H12C H 0.5376 1.4372 0.2941 0.059 Uiso 1 1 calc R . . H12B H 0.7071 1.3845 0.2485 0.059 Uiso 1 1 calc R . . H12A H 0.7014 1.3987 0.3461 0.059 Uiso 1 1 calc R . . C13 C 0.533(2) 1.2816(11) 0.3560(9) 0.031(4) Uani 1 1 d DU . . C14 C 0.524(2) 1.1964(10) 0.3303(11) 0.028(4) Uani 1 1 d DU . . H14 H 0.5810 1.1886 0.2730 0.033 Uiso 1 1 calc R . . C15 C 0.415(3) 1.1249(12) 0.4039(10) 0.044(5) Uani 1 1 d DU . . C16 C 0.238(3) 0.9702(14) 0.4811(13) 0.033(4) Uani 1 1 d U . . C17 C 0.101(2) 0.7994(8) 0.5370(9) 0.033(5) Uani 1 1 d DU . . C18 C 0.013(2) 0.7992(10) 0.6244(8) 0.024(4) Uani 1 1 d DU . . H18 H 0.0186 0.8560 0.6440 0.029 Uiso 1 1 calc R . . C19 C -0.084(2) 0.7117(9) 0.6815(11) 0.026(4) Uani 1 1 d DU . . C20 C -0.103(3) 0.6249(12) 0.6598(11) 0.046(5) Uani 1 1 d DU . . H20 H -0.1753 0.5687 0.7016 0.055 Uiso 1 1 calc R . . C21 C -0.009(2) 0.6253(9) 0.5733(9) 0.036(5) Uani 1 1 d DU . . H21 H -0.0130 0.5681 0.5540 0.043 Uiso 1 1 calc R . . C22 C 0.0902(9) 0.7116(4) 0.5155(5) 0.028(4) Uani 1 1 d DU . . H22 H 0.1553 0.7106 0.4569 0.033 Uiso 1 1 calc R . . Cl2 Cl 0.7060(9) 1.3956(4) -0.3307(5) 0.080(2) Uani 1 1 d RU . . O8 O 0.3052(9) 1.3952(4) 0.5826(5) 0.137(10) Uani 1 1 d RU . . O7 O 0.2009(9) 1.1400(4) 0.6537(5) 0.084(6) Uani 1 1 d RU . . H7A H 0.3039 1.1193 0.6627 0.101 Uiso 1 1 calc R . . C23 C 0.061(3) 1.0665(19) 0.7188(17) 0.063(7) Uani 1 1 d U . . H23A H 0.1140 1.0202 0.7684 0.094 Uiso 1 1 calc R . . H23B H 0.0146 1.0280 0.6859 0.094 Uiso 1 1 calc R . . H23C H -0.0386 1.1026 0.7453 0.094 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 Cl1 0.044(2) 0.043(2) 0.056(3) -0.023(2) 0.0096(19) 0.0036(18) O1 0.035(4) 0.036(4) 0.039(4) -0.012(3) -0.005(3) 0.002(3) N1 0.050(6) 0.050(5) 0.052(5) -0.019(3) -0.010(3) 0.002(3) C1 0.090(10) 0.090(10) 0.091(10) -0.030(4) -0.019(4) 0.002(3) O2 0.059(5) 0.061(5) 0.060(5) -0.021(3) -0.011(3) 0.004(3) N2 0.042(5) 0.042(5) 0.043(5) -0.015(3) -0.008(3) 0.001(3) C2 0.105(12) 0.105(12) 0.106(12) -0.034(5) -0.022(4) 0.002(3) O3 0.054(5) 0.055(5) 0.056(5) -0.021(3) -0.010(3) 0.006(3) N3 0.026(4) 0.028(4) 0.029(4) -0.012(3) -0.001(3) 0.003(3) C3 0.032(5) 0.032(5) 0.033(5) -0.012(3) -0.005(3) 0.002(3) O4 0.034(4) 0.035(4) 0.036(4) -0.012(3) -0.004(3) 0.001(3) N4 0.031(4) 0.032(4) 0.033(4) -0.015(3) -0.004(3) 0.002(3) C4 0.023(5) 0.024(5) 0.026(5) -0.009(3) -0.003(3) 0.000(3) O5 0.048(5) 0.053(5) 0.052(5) -0.018(3) -0.010(3) -0.002(3) N5 0.038(5) 0.039(5) 0.040(5) -0.015(3) -0.008(3) 0.000(3) C5 0.027(5) 0.027(5) 0.027(5) -0.012(3) -0.004(3) 0.001(3) O6 0.078(6) 0.082(6) 0.082(6) -0.024(3) -0.015(3) 0.003(3) N6 0.039(5) 0.041(5) 0.043(5) -0.014(3) -0.009(3) -0.001(3) C6 0.028(5) 0.028(5) 0.029(5) -0.011(3) -0.003(3) 0.002(3) N7 0.028(4) 0.029(4) 0.030(4) -0.010(3) -0.005(3) -0.001(3) C7 0.024(5) 0.028(5) 0.028(5) -0.010(3) -0.004(3) 0.000(3) N8 0.025(4) 0.024(4) 0.028(4) -0.006(3) -0.003(3) 0.002(3) C8 0.033(5) 0.034(5) 0.036(5) -0.014(3) -0.005(3) 0.001(3) N9 0.020(4) 0.025(4) 0.024(4) -0.007(3) 0.000(3) 0.001(3) C9 0.046(6) 0.048(6) 0.049(6) -0.016(3) -0.010(3) 0.001(3) N10 0.031(5) 0.035(5) 0.034(5) -0.009(3) -0.006(3) 0.002(3) C10 0.046(6) 0.047(6) 0.046(6) -0.016(3) -0.009(3) 0.001(3) C11 0.033(5) 0.035(5) 0.035(5) -0.012(3) -0.006(3) 0.002(3) C12 0.039(6) 0.040(6) 0.041(6) -0.013(3) -0.010(3) 0.001(3) C13 0.030(5) 0.031(5) 0.033(5) -0.009(3) -0.007(3) 0.001(3) C14 0.026(5) 0.029(5) 0.028(5) -0.009(3) -0.007(3) 0.000(3) C15 0.043(6) 0.045(6) 0.045(6) -0.015(3) -0.010(3) 0.002(3) C16 0.030(5) 0.034(5) 0.033(5) -0.011(3) -0.004(3) -0.001(3) C17 0.033(5) 0.033(5) 0.035(5) -0.013(3) -0.006(3) 0.000(3) C18 0.021(5) 0.024(5) 0.025(5) -0.007(3) -0.004(3) -0.001(3) C19 0.024(5) 0.027(5) 0.026(5) -0.008(3) -0.004(3) 0.002(3) C20 0.044(6) 0.045(6) 0.047(6) -0.015(3) -0.009(3) 0.001(3) C21 0.036(5) 0.036(5) 0.037(5) -0.012(3) -0.008(3) 0.001(3) C22 0.028(5) 0.028(5) 0.028(5) -0.012(3) -0.004(3) 0.000(3) Cl2 0.080(3) 0.074(3) 0.087(3) -0.029(2) -0.012(2) -0.001(2) O8 0.138(10) 0.137(10) 0.136(10) -0.046(4) -0.028(4) 0.002(3) O7 0.083(6) 0.084(6) 0.085(6) -0.028(3) -0.016(3) 0.001(3) C23 0.062(7) 0.063(7) 0.063(7) -0.020(4) -0.012(3) 0.002(3) _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 O1 C5 1.24(2) . ? N1 C2 1.34(2) . ? N1 N2 1.35(2) . ? C1 C2 1.65(4) . ? O2 N5 1.19(2) . ? N2 C4 1.34(2) . ? C2 C3 1.39(2) . ? O3 N5 1.26(2) . ? N3 C4 1.425(19) . ? N3 C5 1.42(2) . ? C3 C4 1.39(2) . ? O4 C16 1.22(2) . ? N4 C5 1.33(2) . ? N4 C6 1.47(2) . ? O5 N10 1.18(2) . ? N5 C8 1.51(2) . ? O6 N10 1.23(2) . ? N6 C13 1.34(2) . ? N6 N7 1.35(2) . ? C6 C11 1.39(2) . ? C6 C7 1.39(2) . ? N7 C15 1.34(2) . ? C7 C8 1.39(2) . ? N8 C15 1.34(2) . ? N8 C16 1.39(2) . ? C8 C9 1.39(2) . ? N9 C16 1.32(2) . ? N9 C17 1.433(18) . ? C9 C10 1.39(2) . ? N10 C19 1.54(2) . ? C10 C11 1.39(2) . ? C12 C13 1.53(2) . ? C13 C14 1.39(2) . ? C14 C15 1.39(2) . ? C17 C18 1.39(2) . ? C17 C22 1.39(2) . ? C18 C19 1.39(2) . ? C19 C20 1.39(2) . ? C20 C21 1.39(2) . ? C21 C22 1.39(2) . ? O7 C23 1.48(2) . ? 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 N1 N2 99.8(17) . . ? C4 N2 N1 113.1(14) . . ? N1 C2 C3 118.6(19) . . ? N1 C2 C1 125.6(18) . . ? C3 C2 C1 115.7(17) . . ? C4 N3 C5 125.6(14) . . ? C2 C3 C4 98.5(16) . . ? C5 N4 C6 127.4(14) . . ? N2 C4 C3 110.1(14) . . ? N2 C4 N3 124.0(12) . . ? C3 C4 N3 125.7(12) . . ? O2 N5 O3 128.6(18) . . ? O2 N5 C8 120.2(16) . . ? O3 N5 C8 111.1(15) . . ? O1 C5 N4 130.9(16) . . ? O1 C5 N3 117.9(16) . . ? N4 C5 N3 111.3(15) . . ? C13 N6 N7 109.8(13) . . ? C11 C6 C7 123.2(15) . . ? C11 C6 N4 118.1(12) . . ? C7 C6 N4 118.7(12) . . ? C15 N7 N6 108.9(13) . . ? C8 C7 C6 114.2(14) . . ? C15 N8 C16 124.0(15) . . ? C9 C8 C7 125.2(16) . . ? C9 C8 N5 118.7(13) . . ? C7 C8 N5 115.8(13) . . ? C16 N9 C17 126.6(14) . . ? C8 C9 C10 118.0(18) . . ? O5 N10 O6 126.5(18) . . ? O5 N10 C19 117.5(15) . . ? O6 N10 C19 116.0(16) . . ? C11 C10 C9 119.4(18) . . ? C10 C11 C6 120.0(16) . . ? N6 C13 C14 106.6(13) . . ? N6 C13 C12 120.3(12) . . ? C14 C13 C12 133.2(13) . . ? C15 C14 C13 107.4(14) . . ? N7 C15 N8 125.0(13) . . ? N7 C15 C14 107.2(13) . . ? N8 C15 C14 127.7(12) . . ? O4 C16 N9 124.4(18) . . ? O4 C16 N8 121.6(17) . . ? N9 C16 N8 113.3(16) . . ? C18 C17 C22 117.5(12) . . ? C18 C17 N9 123.0(9) . . ? C22 C17 N9 119.0(10) . . ? C17 C18 C19 116.6(14) . . ? C20 C19 C18 126.7(15) . . ? C20 C19 N10 116.4(12) . . ? C18 C19 N10 116.9(12) . . ? C21 C20 C19 115.9(15) . . ? C22 C21 C20 118.3(13) . . ? C21 C22 C17 124.9(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.964 _refine_diff_density_min -0.868 _refine_diff_density_rms 0.238 # Attachment '- NO3 salt.CIF' data_NO3salt _database_code_depnum_ccdc_archive 'CCDC 783196' #TrackingRef '- NO3 salt.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H32 N12 O14' _chemical_formula_weight 712.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 7.6261(3) _cell_length_b 25.9299(11) _cell_length_c 16.0689(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.908(2) _cell_angle_gamma 90.00 _cell_volume 3139.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9657 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type SMART1000 _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 30666 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 30.54 _reflns_number_total 9546 _reflns_number_gt 5157 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker software' _computing_cell_refinement SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-Seed _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^)+(0.0783P)^2^+1.1242P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9546 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1333 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1777 _refine_ls_wR_factor_gt 0.1458 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 O1 O 0.1438(2) 0.25837(6) 0.27280(9) 0.0254(4) Uani 1 1 d . . . N1 N 0.3685(3) 0.39453(7) 0.30872(12) 0.0226(4) Uani 1 1 d . . . H1N H 0.3515 0.4167 0.2668 0.027 Uiso 1 1 calc R . . C1 C 0.5364(4) 0.45505(10) 0.40778(16) 0.0286(6) Uani 1 1 d . . . H1A H 0.5784 0.4701 0.3585 0.043 Uiso 1 1 calc R . . H1B H 0.6360 0.4519 0.4540 0.043 Uiso 1 1 calc R . . H1C H 0.4452 0.4774 0.4253 0.043 Uiso 1 1 calc R . . O2 O -0.2295(2) 0.15979(7) 0.10366(10) 0.0316(4) Uani 1 1 d . . . N2 N 0.3067(3) 0.34567(7) 0.30617(11) 0.0210(4) Uani 1 1 d . . . H2N H 0.2424 0.3308 0.2625 0.025 Uiso 1 1 calc R . . C2 C 0.4607(3) 0.40384(9) 0.38614(14) 0.0214(5) Uani 1 1 d . . . O3 O -0.2529(3) 0.07691(8) 0.10077(12) 0.0444(5) Uani 1 1 d . . . N3 N 0.3185(3) 0.27374(7) 0.39900(11) 0.0209(4) Uani 1 1 d . . . H3N H 0.3633 0.2608 0.4483 0.025 Uiso 1 1 calc R . . C3 C 0.4593(3) 0.35912(9) 0.43295(13) 0.0204(5) Uani 1 1 d . . . H3 H 0.5156 0.3538 0.4893 0.024 Uiso 1 1 calc R . . O4 O 0.8152(2) 0.24159(6) 0.89488(10) 0.0260(4) Uani 1 1 d . . . N4 N 0.1891(3) 0.19524(7) 0.37379(11) 0.0195(4) Uani 1 1 d . . . H4N H 0.2470 0.1889 0.4245 0.023 Uiso 1 1 calc R . . C4 C 0.3596(3) 0.32348(9) 0.38128(13) 0.0196(4) Uani 1 1 d . . . O5 O 1.1493(3) 0.13301(8) 1.06611(11) 0.0355(5) Uani 1 1 d . . . N5 N -0.2010(3) 0.11717(8) 0.13586(12) 0.0250(4) Uani 1 1 d . . . C5 C 0.2095(3) 0.24289(9) 0.34274(13) 0.0190(4) Uani 1 1 d . . . O6 O 1.2165(3) 0.05314(8) 1.05147(13) 0.0468(6) Uani 1 1 d . . . N6 N 0.5795(3) 0.37980(7) 0.86110(12) 0.0219(4) Uani 1 1 d . . . H6N H 0.5986 0.4029 0.9017 0.026 Uiso 1 1 calc R . . C6 C 0.0862(3) 0.15478(8) 0.33445(13) 0.0182(4) Uani 1 1 d . . . O7 O 0.4434(3) 0.23826(8) 0.57474(13) 0.0472(6) Uani 1 1 d . . . N7 N 0.6458(3) 0.33127(7) 0.86512(11) 0.0206(4) Uani 1 1 d . . . H7N H 0.7158 0.3176 0.9082 0.025 Uiso 1 1 calc R . . C7 C -0.0059(3) 0.15740(9) 0.25243(13) 0.0188(4) Uani 1 1 d . . . H7 H -0.0036 0.1876 0.2191 0.023 Uiso 1 1 calc R . . O8 O 0.4012(3) 0.16213(7) 0.52085(10) 0.0366(5) Uani 1 1 d . . . N8 N 0.6269(3) 0.25799(7) 0.77325(11) 0.0228(4) Uani 1 1 d . . . H8N H 0.5780 0.2452 0.7244 0.027 Uiso 1 1 calc R . . C8 C -0.1011(3) 0.11398(9) 0.22178(13) 0.0203(5) Uani 1 1 d . . . O9 O 0.4940(3) 0.17083(10) 0.65335(11) 0.0540(7) Uani 1 1 d . . . N9 N 0.7557(3) 0.17897(7) 0.79370(11) 0.0224(4) Uani 1 1 d . . . H9N H 0.6973 0.1739 0.7427 0.027 Uiso 1 1 calc R . . C9 C -0.1112(3) 0.06919(9) 0.26663(15) 0.0232(5) Uani 1 1 d . . . H9 H -0.1784 0.0405 0.2428 0.028 Uiso 1 1 calc R . . O10 O 0.1223(3) 0.39231(7) 0.13764(11) 0.0315(4) Uani 1 1 d . . . N10 N 1.1411(3) 0.09315(9) 1.02584(12) 0.0274(5) Uani 1 1 d . . . C10 C -0.0189(3) 0.06771(9) 0.34828(15) 0.0247(5) Uani 1 1 d . . . H10 H -0.0227 0.0375 0.3814 0.030 Uiso 1 1 calc R . . O11 O 0.2922(3) 0.45785(7) 0.17564(10) 0.0310(4) Uani 1 1 d . . . N11 N 0.4462(3) 0.19047(9) 0.58278(12) 0.0312(5) Uani 1 1 d . . . C11 C 0.0784(3) 0.10988(9) 0.38150(14) 0.0209(5) Uani 1 1 d . . . H11 H 0.1410 0.1083 0.4374 0.025 Uiso 1 1 calc R . . O12 O 0.1364(3) 0.45583(7) 0.05102(11) 0.0369(5) Uani 1 1 d . . . N12 N 0.1827(3) 0.43461(8) 0.12091(12) 0.0274(5) Uani 1 1 d . . . C12 C 0.3975(3) 0.43802(10) 0.76194(16) 0.0285(6) Uani 1 1 d . . . H12A H 0.2940 0.4428 0.7904 0.043 Uiso 1 1 calc R . . H12B H 0.3601 0.4393 0.7008 0.043 Uiso 1 1 calc R . . H12C H 0.4839 0.4655 0.7789 0.043 Uiso 1 1 calc R . . O13 O -0.1376(3) 0.32987(7) 0.02288(11) 0.0350(5) Uani 1 1 d . . . H13W H -0.0782 0.3559 0.0414 0.042 Uiso 1 1 calc R . . C13 C 0.4802(3) 0.38718(9) 0.78568(14) 0.0221(5) Uani 1 1 d . . . O14 O 0.3375(3) 0.54525(8) 0.02817(11) 0.0417(5) Uani 1 1 d . . . H14W H 0.2759 0.5201 0.0397 0.050 Uiso 1 1 calc R . . C14 C 0.4791(3) 0.34188(9) 0.74066(14) 0.0212(5) Uani 1 1 d . . . H14 H 0.4174 0.3354 0.6856 0.025 Uiso 1 1 calc R . . C15 C 0.5860(3) 0.30769(9) 0.79186(13) 0.0200(5) Uani 1 1 d . . . C16 C 0.7406(3) 0.22679(9) 0.82682(13) 0.0209(5) Uani 1 1 d . . . C17 C 0.8523(3) 0.13704(9) 0.83077(14) 0.0206(5) Uani 1 1 d . . . C18 C 0.9481(3) 0.13737(9) 0.91193(14) 0.0204(5) Uani 1 1 d . . . H18 H 0.9530 0.1673 0.9463 0.024 Uiso 1 1 calc R . . C19 C 1.0357(3) 0.09260(9) 0.94064(14) 0.0226(5) Uani 1 1 d . . . C20 C 1.0329(3) 0.04754(10) 0.89359(16) 0.0274(5) Uani 1 1 d . . . H20 H 1.0938 0.0174 0.9159 0.033 Uiso 1 1 calc R . . C21 C 0.9381(3) 0.04845(10) 0.81316(17) 0.0305(6) Uani 1 1 d . . . H21 H 0.9335 0.0185 0.7789 0.037 Uiso 1 1 calc R . . C22 C 0.8497(3) 0.09262(10) 0.78201(15) 0.0265(5) Uani 1 1 d . . . H22 H 0.7860 0.0926 0.7263 0.032 Uiso 1 1 calc R . . C23 C -0.0833(4) 0.28684(11) 0.07436(16) 0.0368(7) Uani 1 1 d . . . H23A H 0.0340 0.2754 0.0641 0.055 Uiso 1 1 calc R . . H23B H -0.1690 0.2588 0.0610 0.055 Uiso 1 1 calc R . . H23C H -0.0771 0.2965 0.1337 0.055 Uiso 1 1 calc R . . C24 C 0.3304(4) 0.54868(12) -0.06016(17) 0.0401(7) Uani 1 1 d . . . H24A H 0.3954 0.5793 -0.0738 0.060 Uiso 1 1 calc R . . H24B H 0.2063 0.5512 -0.0872 0.060 Uiso 1 1 calc R . . H24C H 0.3844 0.5178 -0.0807 0.060 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 O1 0.0313(10) 0.0250(9) 0.0173(7) 0.0039(6) -0.0046(7) -0.0030(7) N1 0.0260(11) 0.0209(10) 0.0205(9) 0.0024(7) 0.0027(8) -0.0018(8) C1 0.0301(14) 0.0265(13) 0.0284(12) 0.0006(10) 0.0021(10) -0.0038(10) O2 0.0339(10) 0.0385(10) 0.0194(8) 0.0037(7) -0.0055(7) -0.0059(8) N2 0.0236(10) 0.0222(10) 0.0168(9) -0.0012(7) 0.0020(7) -0.0029(8) C2 0.0195(12) 0.0258(12) 0.0195(10) 0.0001(9) 0.0051(9) 0.0015(9) O3 0.0544(14) 0.0381(11) 0.0348(10) -0.0133(9) -0.0119(10) -0.0058(10) N3 0.0245(11) 0.0211(9) 0.0155(8) 0.0013(7) -0.0019(7) -0.0035(8) C3 0.0186(11) 0.0262(12) 0.0157(10) -0.0014(8) 0.0003(8) -0.0004(9) O4 0.0299(10) 0.0276(9) 0.0178(8) -0.0052(6) -0.0046(7) 0.0025(7) N4 0.0232(10) 0.0204(9) 0.0133(8) 0.0007(7) -0.0020(7) -0.0019(8) C4 0.0200(11) 0.0231(11) 0.0156(10) -0.0007(8) 0.0023(8) 0.0011(9) O5 0.0337(11) 0.0484(12) 0.0223(9) -0.0064(8) -0.0021(8) 0.0110(9) N5 0.0228(11) 0.0326(12) 0.0185(9) -0.0077(8) -0.0001(8) -0.0039(9) C5 0.0194(11) 0.0217(11) 0.0155(9) 0.0001(8) 0.0016(8) -0.0008(9) O6 0.0536(14) 0.0435(12) 0.0389(11) 0.0141(9) -0.0064(10) 0.0156(10) N6 0.0248(11) 0.0211(10) 0.0193(9) -0.0002(7) 0.0018(8) -0.0001(8) C6 0.0167(11) 0.0212(11) 0.0169(10) -0.0007(8) 0.0032(8) 0.0001(9) O7 0.0593(15) 0.0393(12) 0.0442(12) -0.0108(9) 0.0121(11) -0.0132(11) N7 0.0219(10) 0.0231(10) 0.0159(9) 0.0014(7) 0.0004(7) 0.0005(8) C7 0.0187(11) 0.0229(11) 0.0150(10) -0.0002(8) 0.0030(8) -0.0005(9) O8 0.0438(12) 0.0412(11) 0.0196(9) -0.0057(7) -0.0112(8) 0.0039(9) N8 0.0254(11) 0.0235(10) 0.0175(9) -0.0019(7) -0.0028(8) 0.0012(8) C8 0.0191(11) 0.0268(12) 0.0151(10) -0.0031(8) 0.0029(8) 0.0017(9) O9 0.0511(14) 0.0880(17) 0.0174(9) 0.0174(10) -0.0116(9) -0.0285(12) N9 0.0254(11) 0.0255(10) 0.0144(8) -0.0047(7) -0.0026(7) 0.0022(8) C9 0.0186(12) 0.0245(12) 0.0262(12) -0.0041(9) 0.0021(9) -0.0024(9) O10 0.0367(11) 0.0276(9) 0.0291(9) 0.0007(7) 0.0014(8) -0.0035(8) N10 0.0226(11) 0.0381(12) 0.0217(10) 0.0056(9) 0.0045(8) 0.0061(9) C10 0.0222(12) 0.0243(12) 0.0277(12) 0.0029(9) 0.0043(10) -0.0012(10) O11 0.0420(11) 0.0292(9) 0.0195(8) -0.0013(7) -0.0031(8) -0.0038(8) N11 0.0286(12) 0.0496(15) 0.0138(9) -0.0011(9) -0.0014(8) -0.0095(10) C11 0.0216(12) 0.0240(12) 0.0165(10) 0.0009(8) 0.0012(9) 0.0010(9) O12 0.0555(13) 0.0341(10) 0.0181(8) 0.0015(7) -0.0037(8) 0.0035(9) N12 0.0353(13) 0.0253(11) 0.0202(10) -0.0023(8) 0.0000(9) 0.0046(9) C12 0.0260(13) 0.0302(13) 0.0284(12) 0.0075(10) 0.0019(10) 0.0027(10) O13 0.0466(12) 0.0297(10) 0.0235(9) 0.0007(7) -0.0105(8) -0.0032(9) C13 0.0190(11) 0.0288(12) 0.0188(10) 0.0045(9) 0.0039(9) -0.0028(9) O14 0.0631(15) 0.0361(11) 0.0263(9) -0.0041(8) 0.0090(9) -0.0077(10) C14 0.0179(11) 0.0278(12) 0.0171(10) 0.0013(9) -0.0001(8) -0.0003(9) C15 0.0181(11) 0.0262(12) 0.0159(10) 0.0012(8) 0.0029(8) -0.0020(9) C16 0.0197(12) 0.0246(12) 0.0176(10) -0.0005(9) 0.0000(9) 0.0003(9) C17 0.0169(11) 0.0256(12) 0.0193(10) -0.0018(9) 0.0027(9) -0.0011(9) C18 0.0181(11) 0.0244(12) 0.0189(10) -0.0013(8) 0.0034(9) -0.0001(9) C19 0.0176(11) 0.0301(12) 0.0209(11) 0.0026(9) 0.0048(9) -0.0001(9) C20 0.0211(12) 0.0243(12) 0.0372(14) 0.0001(10) 0.0053(10) 0.0030(10) C21 0.0266(14) 0.0271(13) 0.0373(14) -0.0106(11) 0.0033(11) -0.0007(11) C22 0.0231(12) 0.0324(13) 0.0232(11) -0.0068(10) 0.0005(9) 0.0003(10) C23 0.0470(18) 0.0359(15) 0.0252(13) 0.0064(11) -0.0015(12) 0.0031(13) C24 0.0444(18) 0.0490(17) 0.0265(13) -0.0008(12) 0.0042(12) 0.0041(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 O1 C5 1.225(2) . ? N1 N2 1.350(3) . ? N1 C2 1.353(3) . ? N1 H1N 0.8800 . ? C1 C2 1.468(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 N5 1.225(3) . ? N2 C4 1.342(3) . ? N2 H2N 0.8800 . ? C2 C3 1.383(3) . ? O3 N5 1.223(3) . ? N3 C4 1.368(3) . ? N3 C5 1.384(3) . ? N3 H3N 0.8800 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? O4 C16 1.214(3) . ? N4 C5 1.350(3) . ? N4 C6 1.401(3) . ? N4 H4N 0.8800 . ? O5 N10 1.216(3) . ? N5 C8 1.472(3) . ? O6 N10 1.226(3) . ? N6 C13 1.340(3) . ? N6 N7 1.354(3) . ? N6 H6N 0.8800 . ? C6 C11 1.395(3) . ? C6 C7 1.396(3) . ? O7 N11 1.246(3) . ? N7 C15 1.342(3) . ? N7 H7N 0.8800 . ? C7 C8 1.388(3) . ? C7 H7 0.9500 . ? O8 N11 1.242(3) . ? N8 C15 1.370(3) . ? N8 C16 1.384(3) . ? N8 H8N 0.8800 . ? C8 C9 1.375(3) . ? O9 N11 1.245(3) . ? N9 C16 1.361(3) . ? N9 C17 1.394(3) . ? N9 H9N 0.8800 . ? C9 C10 1.390(3) . ? C9 H9 0.9500 . ? O10 N12 1.235(3) . ? N10 C19 1.476(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? O11 N12 1.268(3) . ? C11 H11 0.9500 . ? O12 N12 1.251(3) . ? C12 C13 1.485(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O13 C23 1.412(3) . ? O13 H13W 0.8400 . ? C13 C14 1.379(3) . ? O14 C24 1.415(3) . ? O14 H14W 0.8400 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C17 C22 1.391(3) . ? C17 C18 1.393(3) . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.390(3) . ? C20 C21 1.380(4) . ? C20 H20 0.9500 . ? C21 C22 1.383(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 N2 N1 C2 108.95(18) . . ? N2 N1 H1N 125.5 . . ? C2 N1 H1N 125.5 . . ? 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 . . ? C4 N2 N1 108.67(18) . . ? C4 N2 H2N 125.7 . . ? N1 N2 H2N 125.7 . . ? N1 C2 C3 107.7(2) . . ? N1 C2 C1 120.6(2) . . ? C3 C2 C1 131.7(2) . . ? C4 N3 C5 122.88(18) . . ? C4 N3 H3N 118.6 . . ? C5 N3 H3N 118.6 . . ? C2 C3 C4 106.41(19) . . ? C2 C3 H3 126.8 . . ? C4 C3 H3 126.8 . . ? C5 N4 C6 127.37(18) . . ? C5 N4 H4N 116.3 . . ? C6 N4 H4N 116.3 . . ? N2 C4 N3 123.0(2) . . ? N2 C4 C3 108.2(2) . . ? N3 C4 C3 128.7(2) . . ? O3 N5 O2 123.47(19) . . ? O3 N5 C8 117.9(2) . . ? O2 N5 C8 118.62(18) . . ? O1 C5 N4 125.8(2) . . ? O1 C5 N3 121.9(2) . . ? N4 C5 N3 112.29(18) . . ? C13 N6 N7 109.31(18) . . ? C13 N6 H6N 125.3 . . ? N7 N6 H6N 125.3 . . ? C11 C6 C7 119.7(2) . . ? C11 C6 N4 116.65(18) . . ? C7 C6 N4 123.7(2) . . ? C15 N7 N6 107.93(18) . . ? C15 N7 H7N 126.0 . . ? N6 N7 H7N 126.0 . . ? C8 C7 C6 117.0(2) . . ? C8 C7 H7 121.5 . . ? C6 C7 H7 121.5 . . ? C15 N8 C16 123.77(18) . . ? C15 N8 H8N 118.1 . . ? C16 N8 H8N 118.1 . . ? C9 C8 C7 124.6(2) . . ? C9 C8 N5 118.4(2) . . ? C7 C8 N5 117.0(2) . . ? C16 N9 C17 127.90(18) . . ? C16 N9 H9N 116.1 . . ? C17 N9 H9N 116.1 . . ? C8 C9 C10 117.2(2) . . ? C8 C9 H9 121.4 . . ? C10 C9 H9 121.4 . . ? O5 N10 O6 123.9(2) . . ? O5 N10 C19 118.5(2) . . ? O6 N10 C19 117.6(2) . . ? C11 C10 C9 120.4(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? O8 N11 O9 119.6(2) . . ? O8 N11 O7 120.5(2) . . ? O9 N11 O7 120.0(2) . . ? C10 C11 C6 121.1(2) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? O10 N12 O12 121.5(2) . . ? O10 N12 O11 119.94(19) . . ? O12 N12 O11 118.5(2) . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C23 O13 H13W 109.5 . . ? N6 C13 C14 108.0(2) . . ? N6 C13 C12 121.1(2) . . ? C14 C13 C12 130.8(2) . . ? C24 O14 H14W 109.5 . . ? C13 C14 C15 106.2(2) . . ? C13 C14 H14 126.9 . . ? C15 C14 H14 126.9 . . ? N7 C15 N8 124.2(2) . . ? N7 C15 C14 108.5(2) . . ? N8 C15 C14 127.2(2) . . ? O4 C16 N9 125.7(2) . . ? O4 C16 N8 122.4(2) . . ? N9 C16 N8 111.84(18) . . ? C22 C17 C18 119.5(2) . . ? C22 C17 N9 116.38(19) . . ? C18 C17 N9 124.1(2) . . ? C19 C18 C17 117.6(2) . . ? C19 C18 H18 121.2 . . ? C17 C18 H18 121.2 . . ? C18 C19 C20 123.9(2) . . ? C18 C19 N10 117.8(2) . . ? C20 C19 N10 118.2(2) . . ? C21 C20 C19 117.2(2) . . ? C21 C20 H20 121.4 . . ? C19 C20 H20 121.4 . . ? C20 C21 C22 120.6(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C17 121.2(2) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? O13 C23 H23A 109.5 . . ? O13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O14 C24 H24A 109.5 . . ? O14 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O14 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C2 N1 N2 C4 -0.4(3) . . . . ? N2 N1 C2 C3 1.1(3) . . . . ? N2 N1 C2 C1 -177.2(2) . . . . ? N1 C2 C3 C4 -1.4(3) . . . . ? C1 C2 C3 C4 176.7(3) . . . . ? N1 N2 C4 N3 -179.9(2) . . . . ? N1 N2 C4 C3 -0.5(3) . . . . ? C5 N3 C4 N2 -4.1(4) . . . . ? C5 N3 C4 C3 176.7(2) . . . . ? C2 C3 C4 N2 1.2(3) . . . . ? C2 C3 C4 N3 -179.5(2) . . . . ? C6 N4 C5 O1 -2.1(4) . . . . ? C6 N4 C5 N3 178.9(2) . . . . ? C4 N3 C5 O1 0.5(4) . . . . ? C4 N3 C5 N4 179.5(2) . . . . ? C5 N4 C6 C11 -176.4(2) . . . . ? C5 N4 C6 C7 3.7(4) . . . . ? C13 N6 N7 C15 -0.7(3) . . . . ? C11 C6 C7 C8 -0.4(3) . . . . ? N4 C6 C7 C8 179.5(2) . . . . ? C6 C7 C8 C9 0.4(4) . . . . ? C6 C7 C8 N5 178.8(2) . . . . ? O3 N5 C8 C9 -17.2(3) . . . . ? O2 N5 C8 C9 162.0(2) . . . . ? O3 N5 C8 C7 164.3(2) . . . . ? O2 N5 C8 C7 -16.5(3) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? N5 C8 C9 C10 -178.5(2) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C6 0.1(4) . . . . ? C7 C6 C11 C10 0.2(4) . . . . ? N4 C6 C11 C10 -179.7(2) . . . . ? N7 N6 C13 C14 1.4(3) . . . . ? N7 N6 C13 C12 -177.0(2) . . . . ? N6 C13 C14 C15 -1.6(3) . . . . ? C12 C13 C14 C15 176.6(2) . . . . ? N6 N7 C15 N8 179.8(2) . . . . ? N6 N7 C15 C14 -0.3(3) . . . . ? C16 N8 C15 N7 -2.6(4) . . . . ? C16 N8 C15 C14 177.5(2) . . . . ? C13 C14 C15 N7 1.1(3) . . . . ? C13 C14 C15 N8 -178.9(2) . . . . ? C17 N9 C16 O4 2.4(4) . . . . ? C17 N9 C16 N8 -177.3(2) . . . . ? C15 N8 C16 O4 -0.9(4) . . . . ? C15 N8 C16 N9 178.9(2) . . . . ? C16 N9 C17 C22 -178.1(2) . . . . ? C16 N9 C17 C18 2.1(4) . . . . ? C22 C17 C18 C19 -0.6(3) . . . . ? N9 C17 C18 C19 179.2(2) . . . . ? C17 C18 C19 C20 -0.3(4) . . . . ? C17 C18 C19 N10 178.5(2) . . . . ? O5 N10 C19 C18 -1.5(3) . . . . ? O6 N10 C19 C18 179.0(2) . . . . ? O5 N10 C19 C20 177.4(2) . . . . ? O6 N10 C19 C20 -2.2(3) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? N10 C19 C20 C21 -178.0(2) . . . . ? C19 C20 C21 C22 -0.3(4) . . . . ? C20 C21 C22 C17 -0.6(4) . . . . ? C18 C17 C22 C21 1.1(4) . . . . ? N9 C17 C22 C21 -178.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.489 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.072