# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 #TrackingRef 'science.cif' # start Validation Reply Form _vrf_PUBL012_GLOBAL ; PROBLEM: _publ_section_abstract is missing. RESPONSE: ... ; _vrf_PUBL024_GLOBAL ; PROBLEM: The number of authors is greater than 5. RESPONSE: ... ; # end Validation Reply Form #Added by publCIF (Fr 18. Mrz 16:04:36 2011) _audit_update_record ; 2011-03-18 # Formatted by publCIF ; # 1. SUBMISSION DETAILS _publ_contact_author ; Alexander Schiller Institut f\"ur anorganische und analytische Chemie Friedrich-Schiller-Universit\"at Jena August-Bebel-Str. 2 07743 Jena Germany ; _publ_contact_author_phone '03641 948 113' _publ_contact_author_fax '03641 948 102' _publ_contact_author_email Alexander.Schiller@uni-jena.de # 3. TITLE AND AUTHOR LIST _publ_section_title ; Light-triggered NO release from nanofiber non-wovens ; loop_ _publ_author_name _publ_author_address 'Alexander Schiller' ; Institut f\"ur anorganische und analytische Chemie Friedrich-Schiller-Universit\"at Jena August-Bebel-Str. 2 D-07743 Jena Germany ; U.Muller ; INNOVENT e.V. Technologieentwicklung Jena Pr\"ussingstrasse 27 B D-07745 Jena Germany ; 'Martina Frigge' ; INNOVENT e.V. Technologieentwicklung Jena Pr\"ussingstrasse 27 B D-07745 Jena Germany ; 'Matthias Schnabelrauch' ; INNOVENT e.V. Technologieentwicklung Jena Pr\"ussingstrasse 27 B D-07745 Jena Germany ; 'Ralf Wyrwa' ; INNOVENT e.V. Technologieentwicklung Jena Pr\"ussingstrasse 27 B D-07745 Jena Germany ; ; M.Wolfram ; ; Institut f\"ur anorganische und analytische Chemie Friedrich-Schiller-Universit\"at Jena August-Bebel-Str. 2 D-07743 Jena Germany ; 'Carmen Bohlender ' ; Institut f\"ur anorganische und analytische Chemie Friedrich-Schiller-Universit\"at Jena August-Bebel-Str. 2 D-07743 Jena Germany ; 'Wolfgang Imhof ' ; Institut f\"ur anorganische und analytische Chemie Friedrich-Schiller-Universit\"at Jena August-Bebel-Str. 2 D-07743 Jena Germany ; H.Gorls ; Institut f\"ur anorganische und analytische Chemie Friedrich-Schiller-Universit\"at Jena Lessing-Str. 8 D-07743 Jena Germany ; _publ_contact_author_name 'Alexander Schiller' # data_FO4004 _database_code_depnum_ccdc_archive 'CCDC 818041' #TrackingRef 'science.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 N6 O2' _chemical_formula_sum 'C12 H16 N6 O2' _chemical_formula_weight 276.31 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.3673(5) _cell_length_b 14.6310(8) _cell_length_c 9.1018(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.698(3) _cell_angle_gamma 90.00 _cell_volume 1329.10(12) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 8888 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 133(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8888 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3032 _reflns_number_gt 2106 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0666P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3032 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 O1A O 1.13019(9) 0.60068(7) 0.77689(11) 0.0270(3) Uani 1 1 d . . . N1A N 0.94955(12) 0.50956(8) 0.68350(13) 0.0233(3) Uani 1 1 d . . . H1NA H 0.8696(17) 0.4916(11) 0.6920(19) 0.033(5) Uiso 1 1 d . . . N2A N 0.84009(11) 0.57347(8) 0.91888(13) 0.0239(3) Uani 1 1 d . . . N3A N 1.01407(11) 0.66653(8) 1.00890(13) 0.0226(3) Uani 1 1 d . . . C1A C 1.00789(14) 0.46924(10) 0.56982(16) 0.0230(3) Uani 1 1 d . . . H1AB H 0.9614(13) 0.4101(10) 0.5412(16) 0.020(4) Uiso 1 1 d . . . H1AA H 1.1044(16) 0.4583(10) 0.6174(17) 0.030(4) Uiso 1 1 d . . . C2A C 1.01985(13) 0.57127(10) 0.78239(16) 0.0211(3) Uani 1 1 d . . . C3A C 0.95632(13) 0.60284(9) 0.90141(15) 0.0208(3) Uani 1 1 d . . . C4A C 0.82305(15) 0.62039(10) 1.04297(17) 0.0268(3) Uani 1 1 d . . . H4A H 0.7423(15) 0.6106(11) 1.0813(18) 0.034(4) Uiso 1 1 d . . . C5A C 0.92897(14) 0.67738(11) 1.09876(17) 0.0261(3) Uani 1 1 d . . . H5A H 0.9476(14) 0.7185(11) 1.1838(18) 0.030(4) Uiso 1 1 d . . . C6A C 1.14362(15) 0.71342(11) 1.03488(19) 0.0287(4) Uani 1 1 d . . . H6AC H 1.1512(14) 0.7455(11) 0.9397(19) 0.034(4) Uiso 1 1 d . . . H6AB H 1.1495(15) 0.7556(12) 1.123(2) 0.037(4) Uiso 1 1 d . . . H6AA H 1.2200(15) 0.6711(13) 1.0615(19) 0.042(5) Uiso 1 1 d . . . O1B O 0.40219(10) 0.36813(7) 0.75588(12) 0.0304(3) Uani 1 1 d . . . N1B N 0.58672(12) 0.45289(9) 0.85996(13) 0.0229(3) Uani 1 1 d . . . H1NB H 0.6573(16) 0.4809(11) 0.8465(18) 0.030(4) Uiso 1 1 d . . . N2B N 0.66680(11) 0.42976(8) 0.58744(13) 0.0235(3) Uani 1 1 d . . . N3B N 0.47699(11) 0.35694(8) 0.47547(13) 0.0219(3) Uani 1 1 d . . . C1B C 0.55095(14) 0.46213(11) 1.00338(16) 0.0230(3) Uani 1 1 d . . . H1BB H 0.5085(13) 0.4028(11) 1.0269(17) 0.022(4) Uiso 1 1 d . . . H1BA H 0.6318(15) 0.4752(10) 1.0857(17) 0.024(4) Uiso 1 1 d . . . C2B C 0.50622(13) 0.40530(10) 0.74518(16) 0.0221(3) Uani 1 1 d . . . C3B C 0.55110(13) 0.39857(9) 0.60460(16) 0.0211(3) Uani 1 1 d . . . C4B C 0.66473(14) 0.40740(10) 0.44018(17) 0.0251(3) Uani 1 1 d . . . H4B H 0.7387(16) 0.4231(10) 0.3944(18) 0.030(4) Uiso 1 1 d . . . C5B C 0.54926(14) 0.36238(10) 0.37138(17) 0.0248(3) Uani 1 1 d . . . H5B H 0.5159(14) 0.3381(11) 0.2743(19) 0.034(4) Uiso 1 1 d . . . C6B C 0.34172(15) 0.31841(13) 0.4433(2) 0.0314(4) Uani 1 1 d . . . H6BC H 0.3256(15) 0.2876(12) 0.342(2) 0.039(5) Uiso 1 1 d . . . H6BB H 0.3377(17) 0.2745(14) 0.527(2) 0.053(6) Uiso 1 1 d . . . H6A H 0.2747(17) 0.3654(14) 0.440(2) 0.051(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0234(5) 0.0342(6) 0.0272(6) -0.0031(5) 0.0136(4) -0.0050(4) N1A 0.0212(6) 0.0292(7) 0.0224(6) -0.0034(5) 0.0111(5) -0.0018(5) N2A 0.0230(6) 0.0272(7) 0.0244(6) -0.0001(5) 0.0116(5) 0.0009(5) N3A 0.0209(6) 0.0249(7) 0.0235(6) -0.0005(5) 0.0087(5) 0.0021(5) C1A 0.0226(7) 0.0260(8) 0.0232(7) -0.0025(6) 0.0113(6) -0.0009(6) C2A 0.0206(7) 0.0245(7) 0.0200(7) 0.0026(6) 0.0083(6) 0.0028(6) C3A 0.0219(7) 0.0221(7) 0.0194(7) 0.0005(6) 0.0075(6) 0.0015(5) C4A 0.0275(8) 0.0301(8) 0.0275(8) -0.0008(6) 0.0158(7) 0.0026(6) C5A 0.0291(8) 0.0278(8) 0.0241(7) -0.0044(7) 0.0118(7) 0.0030(6) C6A 0.0245(8) 0.0301(9) 0.0321(9) -0.0067(7) 0.0084(7) -0.0034(6) O1B 0.0294(6) 0.0382(6) 0.0287(6) -0.0055(5) 0.0165(5) -0.0100(5) N1B 0.0219(6) 0.0296(7) 0.0207(6) -0.0017(5) 0.0117(5) -0.0020(5) N2B 0.0235(6) 0.0282(7) 0.0226(6) -0.0006(5) 0.0125(5) 0.0002(5) N3B 0.0215(6) 0.0241(7) 0.0220(6) -0.0016(5) 0.0091(5) -0.0005(5) C1B 0.0234(7) 0.0306(8) 0.0174(7) -0.0009(6) 0.0096(6) -0.0010(6) C2B 0.0213(7) 0.0245(8) 0.0233(7) 0.0012(6) 0.0109(6) 0.0021(6) C3B 0.0223(7) 0.0212(7) 0.0213(7) -0.0006(6) 0.0085(6) 0.0002(5) C4B 0.0262(8) 0.0291(8) 0.0243(8) 0.0013(6) 0.0145(6) 0.0016(6) C5B 0.0294(8) 0.0273(8) 0.0208(8) -0.0017(6) 0.0119(7) 0.0025(6) C6B 0.0239(8) 0.0395(10) 0.0313(9) -0.0078(8) 0.0085(7) -0.0063(7) _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 O1A C2A 1.2358(17) . ? N1A C2A 1.3423(18) . ? N1A C1A 1.4571(19) . ? N1A H1NA 0.892(17) . ? N2A C3A 1.3288(17) . ? N2A C4A 1.3734(19) . ? N3A C5A 1.3649(19) . ? N3A C3A 1.3663(18) . ? N3A C6A 1.4692(18) . ? C1A C1A 1.530(3) 3_766 ? C1A H1AB 0.990(15) . ? C1A H1AA 0.990(15) . ? C2A C3A 1.486(2) . ? C4A C5A 1.363(2) . ? C4A H4A 1.000(17) . ? C5A H5A 0.958(16) . ? C6A H6AC 1.007(18) . ? C6A H6AB 1.002(18) . ? C6A H6AA 0.982(17) . ? O1B C2B 1.2350(16) . ? N1B C2B 1.3420(18) . ? N1B C1B 1.4566(18) . ? N1B H1NB 0.876(17) . ? N2B C3B 1.3314(17) . ? N2B C4B 1.3742(19) . ? N3B C5B 1.3599(19) . ? N3B C3B 1.3617(17) . ? N3B C6B 1.4656(18) . ? C1B C1B 1.521(3) 3_667 ? C1B H1BB 1.022(15) . ? C1B H1BA 0.980(15) . ? C2B C3B 1.478(2) . ? C4B C5B 1.361(2) . ? C4B H4B 0.993(16) . ? C5B H5B 0.928(16) . ? C6B H6BC 0.997(18) . ? C6B H6BB 1.01(2) . ? C6B H6A 0.972(19) . ? 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 C2A N1A C1A 119.61(12) . . ? C2A N1A H1NA 119.2(11) . . ? C1A N1A H1NA 121.1(11) . . ? C3A N2A C4A 105.03(12) . . ? C5A N3A C3A 106.22(12) . . ? C5A N3A C6A 124.07(13) . . ? C3A N3A C6A 129.65(12) . . ? N1A C1A C1A 112.34(15) . 3_766 ? N1A C1A H1AB 105.9(8) . . ? C1A C1A H1AB 111.1(8) 3_766 . ? N1A C1A H1AA 108.6(9) . . ? C1A C1A H1AA 109.1(9) 3_766 . ? H1AB C1A H1AA 109.7(12) . . ? O1A C2A N1A 123.21(13) . . ? O1A C2A C3A 121.28(13) . . ? N1A C2A C3A 115.51(12) . . ? N2A C3A N3A 111.76(12) . . ? N2A C3A C2A 125.60(12) . . ? N3A C3A C2A 122.64(12) . . ? C5A C4A N2A 110.02(13) . . ? C5A C4A H4A 128.6(9) . . ? N2A C4A H4A 121.4(10) . . ? C4A C5A N3A 106.97(13) . . ? C4A C5A H5A 130.7(9) . . ? N3A C5A H5A 122.4(9) . . ? N3A C6A H6AC 111.1(8) . . ? N3A C6A H6AB 105.7(9) . . ? H6AC C6A H6AB 113.7(13) . . ? N3A C6A H6AA 112.8(10) . . ? H6AC C6A H6AA 105.1(14) . . ? H6AB C6A H6AA 108.7(13) . . ? C2B N1B C1B 119.36(12) . . ? C2B N1B H1NB 120.1(11) . . ? C1B N1B H1NB 120.5(11) . . ? C3B N2B C4B 104.83(12) . . ? C5B N3B C3B 106.65(12) . . ? C5B N3B C6B 124.15(13) . . ? C3B N3B C6B 129.07(13) . . ? N1B C1B C1B 111.96(15) . 3_667 ? N1B C1B H1BB 109.7(8) . . ? C1B C1B H1BB 107.1(8) 3_667 . ? N1B C1B H1BA 109.3(9) . . ? C1B C1B H1BA 109.3(9) 3_667 . ? H1BB C1B H1BA 109.4(12) . . ? O1B C2B N1B 122.65(13) . . ? O1B C2B C3B 121.67(13) . . ? N1B C2B C3B 115.67(12) . . ? N2B C3B N3B 111.59(12) . . ? N2B C3B C2B 125.68(12) . . ? N3B C3B C2B 122.72(12) . . ? C5B C4B N2B 110.09(13) . . ? C5B C4B H4B 127.0(9) . . ? N2B C4B H4B 123.0(9) . . ? N3B C5B C4B 106.83(13) . . ? N3B C5B H5B 120.5(10) . . ? C4B C5B H5B 132.7(10) . . ? N3B C6B H6BC 105.7(9) . . ? N3B C6B H6BB 109.2(10) . . ? H6BC C6B H6BB 112.2(15) . . ? N3B C6B H6A 111.8(11) . . ? H6BC C6B H6A 110.7(14) . . ? H6BB C6B H6A 107.4(15) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.191 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.050 #==== END data_FO3997 _database_code_depnum_ccdc_archive 'CCDC 818042' #TrackingRef 'science.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N6 O2' _chemical_formula_sum 'C16 H16 N6 O2' _chemical_formula_weight 324.35 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4171(7) _cell_length_b 11.8541(9) _cell_length_c 12.1504(9) _cell_angle_alpha 81.797(4) _cell_angle_beta 73.957(5) _cell_angle_gamma 75.363(5) _cell_volume 1524.40(19) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 10391 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 133(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10391 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.1055 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6870 _reflns_number_gt 3950 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXTL-97 _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^)+(0.0589P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6870 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1230 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.009 _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 O1A O 0.47944(13) 0.22066(14) 0.53189(13) 0.0336(4) Uani 1 1 d . . . O2A O -0.04494(13) 0.31092(15) 0.37208(14) 0.0394(4) Uani 1 1 d . . . N1A N 0.13878(16) 0.34239(16) 0.38884(15) 0.0259(4) Uani 1 1 d . . . N2A N 0.33576(15) 0.18015(16) 0.45349(16) 0.0254(4) Uani 1 1 d . . . N3A N 0.52972(15) 0.09739(16) 0.26500(15) 0.0281(4) Uani 1 1 d . . . N4A N 0.67478(15) 0.13459(16) 0.33602(16) 0.0277(4) Uani 1 1 d . . . N5A N 0.19036(15) 0.42705(16) 0.15899(16) 0.0296(4) Uani 1 1 d . . . N6A N 0.04522(15) 0.35287(16) 0.12323(16) 0.0278(4) Uani 1 1 d . . . C1A C 0.12701(18) 0.30586(19) 0.50704(18) 0.0252(5) Uani 1 1 d . . . C2A C 0.02080(19) 0.3498(2) 0.5918(2) 0.0307(5) Uani 1 1 d . . . H2AA H -0.0494 0.4009 0.5703 0.037 Uiso 1 1 calc R . . C3A C 0.0167(2) 0.3197(2) 0.7068(2) 0.0333(6) Uani 1 1 d . . . H3AA H -0.0563 0.3495 0.7639 0.040 Uiso 1 1 calc R . . C4A C 0.1200(2) 0.2456(2) 0.7388(2) 0.0326(6) Uani 1 1 d . . . H4AA H 0.1182 0.2266 0.8178 0.039 Uiso 1 1 calc R . . C5A C 0.2248(2) 0.2000(2) 0.65549(19) 0.0288(5) Uani 1 1 d . . . H5AA H 0.2946 0.1486 0.6776 0.035 Uiso 1 1 calc R . . C6A C 0.22916(18) 0.22857(19) 0.53949(18) 0.0246(5) Uani 1 1 d . . . C7A C 0.45357(19) 0.18347(19) 0.45411(19) 0.0259(5) Uani 1 1 d . . . C8A C 0.55128(18) 0.13754(18) 0.35244(18) 0.0245(5) Uani 1 1 d . . . C9A C 0.64455(19) 0.06741(19) 0.19008(19) 0.0294(5) Uani 1 1 d . . . H9AA H 0.6598 0.0354 0.1188 0.035 Uiso 1 1 calc R . . C10A C 0.73365(19) 0.09016(19) 0.23268(19) 0.0292(5) Uani 1 1 d . . . H10A H 0.8207 0.0774 0.1970 0.035 Uiso 1 1 calc R . . C11A C 0.7370(2) 0.1790(3) 0.4059(2) 0.0438(7) Uani 1 1 d . . . H11A H 0.7030 0.1576 0.4873 0.066 Uiso 1 1 calc R . . H11B H 0.7226 0.2643 0.3926 0.066 Uiso 1 1 calc R . . H11C H 0.8270 0.1447 0.3843 0.066 Uiso 1 1 calc R . . C12A C 0.05472(19) 0.33937(19) 0.32990(19) 0.0280(5) Uani 1 1 d . . . C13A C 0.09659(18) 0.37342(19) 0.20543(19) 0.0259(5) Uani 1 1 d . . . C14A C 0.19804(19) 0.4409(2) 0.04308(19) 0.0292(5) Uani 1 1 d . . . H14A H 0.2563 0.4772 -0.0130 0.035 Uiso 1 1 calc R . . C15A C 0.11045(19) 0.3954(2) 0.0207(2) 0.0295(5) Uani 1 1 d . . . H15A H 0.0970 0.3934 -0.0527 0.035 Uiso 1 1 calc R . . C16A C -0.0536(2) 0.2908(2) 0.1364(2) 0.0366(6) Uani 1 1 d . . . H16A H -0.0370 0.2175 0.1842 0.055 Uiso 1 1 calc R . . H16B H -0.0561 0.2734 0.0607 0.055 Uiso 1 1 calc R . . H16C H -0.1343 0.3396 0.1733 0.055 Uiso 1 1 calc R . . O1B O 0.65429(12) 0.37527(13) 0.14207(13) 0.0302(4) Uani 1 1 d . . . O2B O 0.24666(13) 0.12362(13) -0.00079(13) 0.0295(4) Uani 1 1 d . . . N1B N 0.37615(16) 0.16054(16) 0.09731(17) 0.0246(4) Uani 1 1 d . . . N2B N 0.46854(17) 0.34957(15) 0.12496(15) 0.0232(4) Uani 1 1 d . . . N3B N 0.35489(15) 0.44257(16) 0.34116(15) 0.0264(4) Uani 1 1 d . . . N4B N 0.51457(15) 0.52525(15) 0.32471(15) 0.0250(4) Uani 1 1 d . . . N5B N 0.21923(16) 0.08269(16) 0.30129(15) 0.0295(4) Uani 1 1 d . . . N6B N 0.13387(15) -0.00534(16) 0.20338(16) 0.0282(4) Uani 1 1 d . . . C1B C 0.46249(18) 0.20501(18) 0.00343(18) 0.0234(5) Uani 1 1 d . . . C2B C 0.50177(19) 0.15666(19) -0.10207(18) 0.0271(5) Uani 1 1 d . . . H2BA H 0.4665 0.0961 -0.1135 0.033 Uiso 1 1 calc R . . C3B C 0.59174(19) 0.1959(2) -0.19067(19) 0.0290(5) Uani 1 1 d . . . H3BA H 0.6176 0.1629 -0.2627 0.035 Uiso 1 1 calc R . . C4B C 0.64400(19) 0.28388(19) -0.17365(19) 0.0281(5) Uani 1 1 d . . . H4BA H 0.7071 0.3099 -0.2336 0.034 Uiso 1 1 calc R . . C5B C 0.60453(18) 0.33368(19) -0.06970(18) 0.0265(5) Uani 1 1 d . . . H5BA H 0.6399 0.3945 -0.0591 0.032 Uiso 1 1 calc R . . C6B C 0.51341(17) 0.29548(18) 0.01966(17) 0.0228(5) Uani 1 1 d . . . C7B C 0.54049(18) 0.38850(18) 0.17680(18) 0.0235(5) Uani 1 1 d . . . C8B C 0.46978(18) 0.44981(18) 0.28082(18) 0.0229(5) Uani 1 1 d . . . C9B C 0.32595(19) 0.5170(2) 0.42655(19) 0.0284(5) Uani 1 1 d . . . H9BA H 0.2496 0.5302 0.4844 0.034 Uiso 1 1 calc R . . C10B C 0.42231(18) 0.5693(2) 0.41643(18) 0.0278(5) Uani 1 1 d . . . H10B H 0.4248 0.6253 0.4639 0.033 Uiso 1 1 calc R . . C11B C 0.63201(19) 0.5644(2) 0.2811(2) 0.0325(6) Uani 1 1 d . . . H11D H 0.7025 0.4980 0.2853 0.049 Uiso 1 1 calc R . . H11E H 0.6325 0.6252 0.3277 0.049 Uiso 1 1 calc R . . H11F H 0.6396 0.5962 0.2011 0.049 Uiso 1 1 calc R . . C12B C 0.27971(18) 0.11863(18) 0.08856(19) 0.0249(5) Uani 1 1 d . . . C13B C 0.21255(18) 0.06650(18) 0.19802(19) 0.0248(5) Uani 1 1 d . . . C14B C 0.1409(2) 0.0196(2) 0.3760(2) 0.0328(6) Uani 1 1 d . . . H14B H 0.1250 0.0153 0.4573 0.039 Uiso 1 1 calc R . . C15B C 0.0892(2) -0.0361(2) 0.3175(2) 0.0351(6) Uani 1 1 d . . . H15B H 0.0333 -0.0864 0.3495 0.042 Uiso 1 1 calc R . . C16B C 0.1096(2) -0.0523(2) 0.1091(2) 0.0362(6) Uani 1 1 d . . . H16D H 0.0792 0.0123 0.0568 0.054 Uiso 1 1 calc R . . H16E H 0.0463 -0.0989 0.1400 0.054 Uiso 1 1 calc R . . H16F H 0.1871 -0.1019 0.0672 0.054 Uiso 1 1 calc R . . H2NB H 0.390(2) 0.363(2) 0.153(2) 0.038(7) Uiso 1 1 d . . . H2NA H 0.326(2) 0.154(2) 0.392(2) 0.042(7) Uiso 1 1 d . . . H1NA H 0.216(2) 0.365(2) 0.350(2) 0.057(8) Uiso 1 1 d . . . H1NB H 0.3968(19) 0.149(2) 0.161(2) 0.028(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.0321(8) 0.0416(10) 0.0307(9) -0.0120(8) -0.0076(7) -0.0102(7) O2A 0.0276(8) 0.0545(11) 0.0387(10) -0.0055(9) -0.0044(7) -0.0171(8) N1A 0.0217(9) 0.0299(11) 0.0264(11) -0.0009(9) -0.0047(8) -0.0083(8) N2A 0.0251(10) 0.0267(11) 0.0251(11) -0.0066(9) -0.0062(8) -0.0050(8) N3A 0.0287(10) 0.0276(11) 0.0284(11) -0.0048(9) -0.0071(8) -0.0056(8) N4A 0.0249(9) 0.0290(11) 0.0297(11) -0.0051(9) -0.0060(8) -0.0066(8) N5A 0.0261(9) 0.0305(11) 0.0326(11) -0.0049(9) -0.0070(8) -0.0066(8) N6A 0.0247(9) 0.0274(11) 0.0330(11) -0.0058(9) -0.0100(8) -0.0037(8) C1A 0.0250(11) 0.0251(12) 0.0265(12) -0.0050(10) -0.0030(9) -0.0096(9) C2A 0.0268(11) 0.0264(13) 0.0372(14) -0.0059(11) -0.0024(10) -0.0071(10) C3A 0.0316(12) 0.0337(14) 0.0326(14) -0.0089(11) 0.0039(10) -0.0135(11) C4A 0.0382(13) 0.0359(14) 0.0267(13) -0.0063(11) -0.0035(10) -0.0167(11) C5A 0.0328(12) 0.0283(13) 0.0275(13) -0.0018(10) -0.0066(10) -0.0122(10) C6A 0.0244(11) 0.0241(12) 0.0266(13) -0.0059(10) -0.0026(9) -0.0098(9) C7A 0.0316(12) 0.0219(12) 0.0251(12) -0.0002(10) -0.0081(9) -0.0073(9) C8A 0.0269(11) 0.0218(12) 0.0254(12) -0.0016(10) -0.0070(9) -0.0060(9) C9A 0.0318(12) 0.0274(13) 0.0272(13) -0.0065(10) -0.0025(10) -0.0063(10) C10A 0.0252(11) 0.0282(13) 0.0299(13) -0.0044(10) -0.0007(9) -0.0043(9) C11A 0.0280(12) 0.0672(19) 0.0413(15) -0.0159(14) -0.0115(11) -0.0102(12) C12A 0.0240(11) 0.0254(12) 0.0330(13) -0.0048(10) -0.0049(10) -0.0038(9) C13A 0.0214(11) 0.0249(12) 0.0319(13) -0.0061(10) -0.0079(9) -0.0027(9) C14A 0.0277(11) 0.0313(13) 0.0273(13) -0.0043(10) -0.0057(9) -0.0045(10) C15A 0.0284(12) 0.0309(13) 0.0282(13) -0.0036(10) -0.0088(10) -0.0021(10) C16A 0.0328(12) 0.0422(15) 0.0419(15) -0.0039(12) -0.0156(10) -0.0143(11) O1B 0.0231(8) 0.0337(9) 0.0349(9) -0.0061(7) -0.0079(6) -0.0058(7) O2B 0.0298(8) 0.0315(9) 0.0295(9) -0.0046(7) -0.0095(7) -0.0072(7) N1B 0.0277(10) 0.0265(11) 0.0223(11) -0.0032(9) -0.0058(8) -0.0105(8) N2B 0.0225(10) 0.0245(10) 0.0240(10) -0.0056(8) -0.0050(8) -0.0067(8) N3B 0.0275(9) 0.0282(10) 0.0237(10) 0.0004(8) -0.0072(8) -0.0071(8) N4B 0.0255(9) 0.0272(10) 0.0252(10) -0.0037(8) -0.0082(7) -0.0079(8) N5B 0.0333(10) 0.0274(11) 0.0283(11) -0.0050(9) -0.0039(8) -0.0100(8) N6B 0.0258(9) 0.0280(11) 0.0310(11) -0.0055(9) -0.0026(8) -0.0093(8) C1B 0.0236(10) 0.0220(12) 0.0236(12) -0.0013(9) -0.0038(9) -0.0056(9) C2B 0.0319(12) 0.0225(12) 0.0279(12) -0.0052(10) -0.0068(9) -0.0065(9) C3B 0.0302(12) 0.0299(13) 0.0243(12) -0.0047(10) -0.0042(9) -0.0036(10) C4B 0.0272(11) 0.0268(13) 0.0269(13) 0.0022(10) -0.0047(9) -0.0049(9) C5B 0.0267(11) 0.0243(12) 0.0294(13) 0.0010(10) -0.0086(9) -0.0071(9) C6B 0.0232(10) 0.0210(12) 0.0244(12) -0.0021(9) -0.0079(9) -0.0029(9) C7B 0.0275(12) 0.0179(11) 0.0269(12) 0.0018(9) -0.0103(9) -0.0064(9) C8B 0.0253(11) 0.0214(12) 0.0253(12) -0.0007(9) -0.0104(9) -0.0074(9) C9B 0.0280(11) 0.0321(13) 0.0258(12) -0.0047(10) -0.0059(9) -0.0074(10) C10B 0.0322(12) 0.0284(13) 0.0241(12) -0.0051(10) -0.0084(9) -0.0058(10) C11B 0.0294(12) 0.0350(14) 0.0377(14) -0.0082(11) -0.0064(10) -0.0145(10) C12B 0.0252(11) 0.0211(12) 0.0280(13) -0.0064(10) -0.0049(9) -0.0038(9) C13B 0.0247(11) 0.0214(12) 0.0299(13) -0.0055(10) -0.0062(9) -0.0065(9) C14B 0.0371(13) 0.0328(14) 0.0261(13) -0.0036(11) -0.0003(10) -0.0114(11) C15B 0.0307(12) 0.0349(14) 0.0367(14) -0.0059(12) 0.0033(10) -0.0135(11) C16B 0.0383(13) 0.0380(14) 0.0388(15) -0.0058(12) -0.0106(11) -0.0176(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 O1A C7A 1.230(3) . ? O2A C12A 1.222(2) . ? N1A C12A 1.356(3) . ? N1A C1A 1.419(3) . ? N1A H1NA 0.96(3) . ? N2A C7A 1.358(3) . ? N2A C6A 1.421(3) . ? N2A H2NA 0.89(3) . ? N3A C8A 1.328(3) . ? N3A C9A 1.368(3) . ? N4A C10A 1.360(3) . ? N4A C8A 1.360(3) . ? N4A C11A 1.467(3) . ? N5A C13A 1.333(3) . ? N5A C14A 1.375(3) . ? N6A C15A 1.364(3) . ? N6A C13A 1.366(3) . ? N6A C16A 1.459(3) . ? C1A C2A 1.395(3) . ? C1A C6A 1.402(3) . ? C2A C3A 1.383(3) . ? C2A H2AA 0.9500 . ? C3A C4A 1.395(3) . ? C3A H3AA 0.9500 . ? C4A C5A 1.382(3) . ? C4A H4AA 0.9500 . ? C5A C6A 1.392(3) . ? C5A H5AA 0.9500 . ? C7A C8A 1.480(3) . ? C9A C10A 1.358(3) . ? C9A H9AA 0.9500 . ? C10A H10A 0.9500 . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C12A C13A 1.484(3) . ? C14A C15A 1.353(3) . ? C14A H14A 0.9500 . ? C15A H15A 0.9500 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? O1B C7B 1.226(2) . ? O2B C12B 1.233(3) . ? N1B C12B 1.351(3) . ? N1B C1B 1.421(3) . ? N1B H1NB 0.85(2) . ? N2B C7B 1.358(3) . ? N2B C6B 1.420(3) . ? N2B H2NB 0.85(2) . ? N3B C8B 1.331(2) . ? N3B C9B 1.374(3) . ? N4B C10B 1.365(3) . ? N4B C8B 1.365(3) . ? N4B C11B 1.465(3) . ? N5B C13B 1.321(3) . ? N5B C14B 1.371(3) . ? N6B C13B 1.369(3) . ? N6B C15B 1.370(3) . ? N6B C16B 1.461(3) . ? C1B C2B 1.391(3) . ? C1B C6B 1.402(3) . ? C2B C3B 1.385(3) . ? C2B H2BA 0.9500 . ? C3B C4B 1.389(3) . ? C3B H3BA 0.9500 . ? C4B C5B 1.382(3) . ? C4B H4BA 0.9500 . ? C5B C6B 1.393(3) . ? C5B H5BA 0.9500 . ? C7B C8B 1.476(3) . ? C9B C10B 1.363(3) . ? C9B H9BA 0.9500 . ? C10B H10B 0.9500 . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C12B C13B 1.477(3) . ? C14B C15B 1.361(3) . ? C14B H14B 0.9500 . ? C15B H15B 0.9500 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 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 C12A N1A C1A 124.69(18) . . ? C12A N1A H1NA 120.7(16) . . ? C1A N1A H1NA 114.5(16) . . ? C7A N2A C6A 122.32(19) . . ? C7A N2A H2NA 117.3(15) . . ? C6A N2A H2NA 120.0(15) . . ? C8A N3A C9A 105.01(17) . . ? C10A N4A C8A 106.27(18) . . ? C10A N4A C11A 124.06(18) . . ? C8A N4A C11A 129.44(18) . . ? C13A N5A C14A 105.20(18) . . ? C15A N6A C13A 106.62(18) . . ? C15A N6A C16A 124.60(19) . . ? C13A N6A C16A 128.65(19) . . ? C2A C1A C6A 119.3(2) . . ? C2A C1A N1A 122.20(19) . . ? C6A C1A N1A 118.39(17) . . ? C3A C2A C1A 120.6(2) . . ? C3A C2A H2AA 119.7 . . ? C1A C2A H2AA 119.7 . . ? C2A C3A C4A 119.9(2) . . ? C2A C3A H3AA 120.0 . . ? C4A C3A H3AA 120.0 . . ? C5A C4A C3A 119.9(2) . . ? C5A C4A H4AA 120.0 . . ? C3A C4A H4AA 120.0 . . ? C4A C5A C6A 120.5(2) . . ? C4A C5A H5AA 119.7 . . ? C6A C5A H5AA 119.7 . . ? C5A C6A C1A 119.67(18) . . ? C5A C6A N2A 120.77(19) . . ? C1A C6A N2A 119.56(19) . . ? O1A C7A N2A 123.93(19) . . ? O1A C7A C8A 121.63(19) . . ? N2A C7A C8A 114.44(19) . . ? N3A C8A N4A 111.67(18) . . ? N3A C8A C7A 124.72(18) . . ? N4A C8A C7A 123.58(19) . . ? C10A C9A N3A 109.99(19) . . ? C10A C9A H9AA 125.0 . . ? N3A C9A H9AA 125.0 . . ? C9A C10A N4A 107.05(18) . . ? C9A C10A H10A 126.5 . . ? N4A C10A H10A 126.5 . . ? N4A C11A H11A 109.5 . . ? N4A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? N4A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? O2A C12A N1A 125.0(2) . . ? O2A C12A C13A 122.2(2) . . ? N1A C12A C13A 112.82(18) . . ? N5A C13A N6A 111.06(19) . . ? N5A C13A C12A 124.3(2) . . ? N6A C13A C12A 124.58(19) . . ? C15A C14A N5A 110.1(2) . . ? C15A C14A H14A 125.0 . . ? N5A C14A H14A 125.0 . . ? C14A C15A N6A 107.1(2) . . ? C14A C15A H15A 126.5 . . ? N6A C15A H15A 126.5 . . ? N6A C16A H16A 109.5 . . ? N6A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? N6A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C12B N1B C1B 125.13(19) . . ? C12B N1B H1NB 119.0(15) . . ? C1B N1B H1NB 114.8(15) . . ? C7B N2B C6B 124.68(18) . . ? C7B N2B H2NB 119.1(16) . . ? C6B N2B H2NB 116.0(16) . . ? C8B N3B C9B 104.86(17) . . ? C10B N4B C8B 106.71(17) . . ? C10B N4B C11B 123.59(18) . . ? C8B N4B C11B 129.49(17) . . ? C13B N5B C14B 105.04(18) . . ? C13B N6B C15B 106.30(18) . . ? C13B N6B C16B 128.58(18) . . ? C15B N6B C16B 124.83(19) . . ? C2B C1B C6B 119.60(19) . . ? C2B C1B N1B 121.24(19) . . ? C6B C1B N1B 119.09(18) . . ? C3B C2B C1B 120.7(2) . . ? C3B C2B H2BA 119.7 . . ? C1B C2B H2BA 119.7 . . ? C2B C3B C4B 119.6(2) . . ? C2B C3B H3BA 120.2 . . ? C4B C3B H3BA 120.2 . . ? C5B C4B C3B 120.2(2) . . ? C5B C4B H4BA 119.9 . . ? C3B C4B H4BA 119.9 . . ? C4B C5B C6B 120.6(2) . . ? C4B C5B H5BA 119.7 . . ? C6B C5B H5BA 119.7 . . ? C5B C6B C1B 119.23(19) . . ? C5B C6B N2B 120.94(19) . . ? C1B C6B N2B 119.79(18) . . ? O1B C7B N2B 124.22(19) . . ? O1B C7B C8B 121.65(19) . . ? N2B C7B C8B 114.14(17) . . ? N3B C8B N4B 111.52(18) . . ? N3B C8B C7B 125.40(18) . . ? N4B C8B C7B 123.04(17) . . ? C10B C9B N3B 110.37(18) . . ? C10B C9B H9BA 124.8 . . ? N3B C9B H9BA 124.8 . . ? C9B C10B N4B 106.52(19) . . ? C9B C10B H10B 126.7 . . ? N4B C10B H10B 126.7 . . ? N4B C11B H11D 109.5 . . ? N4B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? N4B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? O2B C12B N1B 124.7(2) . . ? O2B C12B C13B 121.27(19) . . ? N1B C12B C13B 113.98(19) . . ? N5B C13B N6B 111.77(18) . . ? N5B C13B C12B 125.42(19) . . ? N6B C13B C12B 122.81(19) . . ? C15B C14B N5B 110.6(2) . . ? C15B C14B H14B 124.7 . . ? N5B C14B H14B 124.7 . . ? C14B C15B N6B 106.3(2) . . ? C14B C15B H15B 126.8 . . ? N6B C15B H15B 126.8 . . ? N6B C16B H16D 109.5 . . ? N6B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? N6B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.246 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.054 #===== END data_FO4066 _database_code_depnum_ccdc_archive 'CCDC 818043' #TrackingRef 'science.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 Cl N7 O3 Ru, C2 H3 N' _chemical_formula_sum 'C18 H17 Cl N8 O3 Ru' _chemical_formula_weight 529.92 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' Ru Ru -1.2594 0.8363 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0329(7) _cell_length_b 10.7389(7) _cell_length_c 12.3584(9) _cell_angle_alpha 91.756(6) _cell_angle_beta 97.964(4) _cell_angle_gamma 104.935(5) _cell_volume 1017.69(13) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 7188 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.941 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 133(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 Kappa_CCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7188 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.46 _reflns_number_total 4605 _reflns_number_gt 3410 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0407P)^2^+1.9205P] 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 4605 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Ru1 Ru 0.73456(5) 0.45749(3) 0.28973(3) 0.01985(12) Uani 1 1 d . . . Cl1 Cl 0.59352(16) 0.49077(11) 0.12087(11) 0.0340(3) Uani 1 1 d . . . O1 O 0.2595(4) 0.4474(3) 0.3845(3) 0.0270(7) Uani 1 1 d . . . O2 O 1.0794(4) 0.8058(3) 0.2540(3) 0.0294(8) Uani 1 1 d . . . O3 O 0.9046(4) 0.3598(3) 0.4774(3) 0.0320(8) Uani 1 1 d . . . N1 N 0.5402(5) 0.2807(3) 0.2752(3) 0.0249(9) Uani 1 1 d . . . N2 N 0.2750(5) 0.1859(3) 0.3019(3) 0.0260(9) Uani 1 1 d . . . N3 N 0.5476(4) 0.5136(3) 0.3543(3) 0.0202(8) Uani 1 1 d . . . N4 N 0.8527(5) 0.6466(3) 0.3050(3) 0.0212(8) Uani 1 1 d . . . N5 N 1.1681(4) 0.5862(3) 0.1423(3) 0.0235(8) Uani 1 1 d . . . N6 N 0.9434(5) 0.4606(3) 0.2037(3) 0.0217(8) Uani 1 1 d . . . N7 N 0.8401(5) 0.4088(3) 0.4077(3) 0.0235(8) Uani 1 1 d . . . C1 C 0.5046(6) 0.1530(4) 0.2410(4) 0.0294(11) Uani 1 1 d . . . H1A H 0.5818 0.1128 0.2107 0.035 Uiso 1 1 calc R . . C2 C 0.3398(6) 0.0932(4) 0.2578(4) 0.0322(12) Uani 1 1 d . . . H2A H 0.2812 0.0043 0.2420 0.039 Uiso 1 1 calc R . . C3 C 0.3993(6) 0.2983(4) 0.3123(4) 0.0240(10) Uani 1 1 d . . . C4 C 0.3904(6) 0.4285(4) 0.3560(4) 0.0212(10) Uani 1 1 d . . . C5 C 0.5884(6) 0.6494(4) 0.3747(4) 0.0224(10) Uani 1 1 d . . . C6 C 0.4774(6) 0.7154(4) 0.4131(4) 0.0281(11) Uani 1 1 d . . . H6A H 0.3675 0.6687 0.4298 0.034 Uiso 1 1 calc R . . C7 C 0.5271(7) 0.8489(4) 0.4268(4) 0.0330(12) Uani 1 1 d . . . H7A H 0.4506 0.8937 0.4522 0.040 Uiso 1 1 calc R . . C8 C 0.6875(7) 0.9175(4) 0.4037(4) 0.0352(12) Uani 1 1 d . . . H8A H 0.7210 1.0090 0.4145 0.042 Uiso 1 1 calc R . . C9 C 0.8003(6) 0.8547(4) 0.3652(4) 0.0308(12) Uani 1 1 d . . . H9A H 0.9101 0.9031 0.3495 0.037 Uiso 1 1 calc R . . C10 C 0.7521(6) 0.7196(4) 0.3494(4) 0.0214(10) Uani 1 1 d . . . C11 C 0.9964(5) 0.6924(4) 0.2578(4) 0.0220(10) Uani 1 1 d . . . C12 C 1.0410(5) 0.5822(4) 0.2038(4) 0.0216(10) Uani 1 1 d . . . C13 C 1.1484(6) 0.4619(4) 0.1011(4) 0.0255(10) Uani 1 1 d . . . H13A H 1.2192 0.4350 0.0546 0.031 Uiso 1 1 calc R . . C14 C 1.0096(5) 0.3848(4) 0.1390(4) 0.0226(10) Uani 1 1 d . . . H14A H 0.9659 0.2941 0.1235 0.027 Uiso 1 1 calc R . . C15 C 0.1018(6) 0.1628(5) 0.3356(5) 0.0361(13) Uani 1 1 d . . . H15A H 0.0765 0.2457 0.3503 0.054 Uiso 1 1 calc R . . H15B H 0.0998 0.1153 0.4021 0.054 Uiso 1 1 calc R . . H15C H 0.0136 0.1119 0.2769 0.054 Uiso 1 1 calc R . . C16 C 1.3012(6) 0.7006(4) 0.1192(4) 0.0304(11) Uani 1 1 d . . . H16A H 1.2449 0.7675 0.0937 0.046 Uiso 1 1 calc R . . H16B H 1.3634 0.6768 0.0624 0.046 Uiso 1 1 calc R . . H16C H 1.3840 0.7339 0.1861 0.046 Uiso 1 1 calc R . . N1EA N 0.8088(8) 1.0572(5) 0.0791(5) 0.0624(16) Uani 1 1 d . . . C1EA C 0.7918(8) 0.9508(5) 0.0576(5) 0.0428(14) Uani 1 1 d . . . C2EA C 0.7706(8) 0.8155(5) 0.0319(5) 0.0478(15) Uani 1 1 d . . . H2E1 H 0.8819 0.8020 0.0175 0.072 Uiso 1 1 calc R . . H2E2 H 0.6825 0.7859 -0.0332 0.072 Uiso 1 1 calc R . . H2E3 H 0.7331 0.7665 0.0938 0.072 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 Ru1 0.01567(18) 0.01388(17) 0.0305(2) 0.00022(13) 0.00765(14) 0.00286(12) Cl1 0.0292(6) 0.0350(6) 0.0398(8) 0.0044(5) 0.0096(5) 0.0095(5) O1 0.0194(16) 0.0287(17) 0.035(2) 0.0036(14) 0.0134(14) 0.0054(13) O2 0.0233(17) 0.0159(15) 0.049(2) -0.0001(14) 0.0149(15) 0.0002(13) O3 0.0283(18) 0.0336(18) 0.037(2) 0.0081(16) 0.0087(16) 0.0103(15) N1 0.024(2) 0.0162(17) 0.033(2) 0.0014(16) 0.0070(17) 0.0029(15) N2 0.020(2) 0.0210(19) 0.034(2) 0.0051(16) 0.0059(17) -0.0005(15) N3 0.0192(18) 0.0169(17) 0.026(2) -0.0015(15) 0.0094(16) 0.0044(14) N4 0.0182(18) 0.0152(17) 0.030(2) -0.0019(15) 0.0083(16) 0.0016(14) N5 0.0148(18) 0.0227(18) 0.034(2) 0.0011(16) 0.0084(16) 0.0051(15) N6 0.0160(18) 0.0176(17) 0.031(2) -0.0004(15) 0.0053(16) 0.0038(14) N7 0.021(2) 0.0164(18) 0.034(2) 0.0058(16) 0.0079(18) 0.0045(15) C1 0.030(3) 0.015(2) 0.045(3) 0.0010(19) 0.012(2) 0.0053(19) C2 0.030(3) 0.017(2) 0.046(3) 0.000(2) 0.005(2) 0.0002(19) C3 0.018(2) 0.020(2) 0.032(3) 0.0046(19) 0.005(2) 0.0006(17) C4 0.019(2) 0.021(2) 0.023(3) 0.0034(18) 0.0058(19) 0.0029(18) C5 0.022(2) 0.017(2) 0.029(3) 0.0019(18) 0.0055(19) 0.0055(17) C6 0.030(3) 0.027(2) 0.032(3) 0.004(2) 0.016(2) 0.009(2) C7 0.041(3) 0.024(2) 0.041(3) -0.002(2) 0.018(2) 0.016(2) C8 0.043(3) 0.017(2) 0.049(3) 0.001(2) 0.019(3) 0.008(2) C9 0.034(3) 0.017(2) 0.045(3) 0.003(2) 0.023(2) 0.0051(19) C10 0.024(2) 0.014(2) 0.030(3) 0.0017(17) 0.0100(19) 0.0085(17) C11 0.015(2) 0.017(2) 0.035(3) 0.0026(18) 0.0064(19) 0.0048(17) C12 0.015(2) 0.021(2) 0.030(3) 0.0062(18) 0.0037(19) 0.0053(17) C13 0.023(2) 0.025(2) 0.032(3) -0.0011(19) 0.006(2) 0.0117(19) C14 0.019(2) 0.020(2) 0.030(3) -0.0037(18) 0.0040(19) 0.0084(17) C15 0.030(3) 0.028(3) 0.049(4) 0.005(2) 0.018(2) 0.000(2) C16 0.022(2) 0.027(2) 0.042(3) 0.004(2) 0.013(2) 0.0001(19) N1EA 0.077(4) 0.034(3) 0.076(4) -0.009(3) 0.014(3) 0.014(3) C1EA 0.048(3) 0.039(3) 0.042(4) 0.000(3) 0.010(3) 0.012(3) C2EA 0.055(4) 0.031(3) 0.056(4) -0.001(3) 0.007(3) 0.010(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 Ru1 N7 1.747(4) . ? Ru1 N4 1.999(3) . ? Ru1 N3 2.006(3) . ? Ru1 N6 2.100(4) . ? Ru1 N1 2.109(3) . ? Ru1 Cl1 2.3163(14) . ? O1 C4 1.216(5) . ? O2 C11 1.234(5) . ? O3 N7 1.154(5) . ? N1 C3 1.332(6) . ? N1 C1 1.368(5) . ? N2 C3 1.343(5) . ? N2 C2 1.368(6) . ? N2 C15 1.470(6) . ? N3 C4 1.358(5) . ? N3 C5 1.416(5) . ? N4 C11 1.351(5) . ? N4 C10 1.412(5) . ? N5 C12 1.347(6) . ? N5 C13 1.376(5) . ? N5 C16 1.471(5) . ? N6 C12 1.339(5) . ? N6 C14 1.374(5) . ? C1 C2 1.362(6) . ? C1 H1A 0.9500 . ? C2 H2A 0.9500 . ? C3 C4 1.506(6) . ? C5 C6 1.394(6) . ? C5 C10 1.419(6) . ? C6 C7 1.384(6) . ? C6 H6A 0.9500 . ? C7 C8 1.382(7) . ? C7 H7A 0.9500 . ? C8 C9 1.384(7) . ? C8 H8A 0.9500 . ? C9 C10 1.402(6) . ? C9 H9A 0.9500 . ? C11 C12 1.487(6) . ? C13 C14 1.357(6) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1EA C1EA 1.133(7) . ? C1EA C2EA 1.439(7) . ? C2EA H2E1 0.9800 . ? C2EA H2E2 0.9800 . ? C2EA H2E3 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 N7 Ru1 N4 99.89(16) . . ? N7 Ru1 N3 99.25(16) . . ? N4 Ru1 N3 83.29(14) . . ? N7 Ru1 N6 92.48(16) . . ? N4 Ru1 N6 79.91(14) . . ? N3 Ru1 N6 160.93(14) . . ? N7 Ru1 N1 89.53(15) . . ? N4 Ru1 N1 161.76(15) . . ? N3 Ru1 N1 79.78(14) . . ? N6 Ru1 N1 115.51(14) . . ? N7 Ru1 Cl1 171.03(12) . . ? N4 Ru1 Cl1 87.59(11) . . ? N3 Ru1 Cl1 86.46(11) . . ? N6 Ru1 Cl1 83.91(11) . . ? N1 Ru1 Cl1 84.66(11) . . ? C3 N1 C1 107.3(4) . . ? C3 N1 Ru1 109.7(3) . . ? C1 N1 Ru1 143.0(3) . . ? C3 N2 C2 108.0(4) . . ? C3 N2 C15 126.9(4) . . ? C2 N2 C15 125.0(4) . . ? C4 N3 C5 126.4(4) . . ? C4 N3 Ru1 120.2(3) . . ? C5 N3 Ru1 112.3(3) . . ? C11 N4 C10 126.9(3) . . ? C11 N4 Ru1 119.7(3) . . ? C10 N4 Ru1 112.3(3) . . ? C12 N5 C13 107.1(3) . . ? C12 N5 C16 127.6(4) . . ? C13 N5 C16 125.3(4) . . ? C12 N6 C14 107.1(4) . . ? C12 N6 Ru1 109.6(3) . . ? C14 N6 Ru1 142.9(3) . . ? O3 N7 Ru1 170.2(3) . . ? C2 C1 N1 108.4(4) . . ? C2 C1 H1A 125.8 . . ? N1 C1 H1A 125.8 . . ? C1 C2 N2 106.7(4) . . ? C1 C2 H2A 126.6 . . ? N2 C2 H2A 126.6 . . ? N1 C3 N2 109.6(4) . . ? N1 C3 C4 122.3(3) . . ? N2 C3 C4 128.2(4) . . ? O1 C4 N3 129.1(4) . . ? O1 C4 C3 122.9(4) . . ? N3 C4 C3 107.9(4) . . ? C6 C5 N3 124.5(4) . . ? C6 C5 C10 119.8(4) . . ? N3 C5 C10 115.6(4) . . ? C7 C6 C5 120.1(4) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C8 C7 C6 120.2(5) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C9 121.0(4) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? C8 C9 C10 119.8(4) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C9 C10 N4 124.4(4) . . ? C9 C10 C5 119.0(4) . . ? N4 C10 C5 116.5(3) . . ? O2 C11 N4 128.2(4) . . ? O2 C11 C12 122.8(4) . . ? N4 C11 C12 108.9(3) . . ? N6 C12 N5 110.0(4) . . ? N6 C12 C11 121.7(4) . . ? N5 C12 C11 128.0(4) . . ? C14 C13 N5 107.6(4) . . ? C14 C13 H13A 126.2 . . ? N5 C13 H13A 126.2 . . ? C13 C14 N6 108.1(4) . . ? C13 C14 H14A 125.9 . . ? N6 C14 H14A 125.9 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N5 C16 H16A 109.5 . . ? N5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1EA C1EA C2EA 179.2(7) . . ? C1EA C2EA H2E1 109.5 . . ? C1EA C2EA H2E2 109.5 . . ? H2E1 C2EA H2E2 109.5 . . ? C1EA C2EA H2E3 109.5 . . ? H2E1 C2EA H2E3 109.5 . . ? H2E2 C2EA H2E3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.585 _refine_diff_density_min -0.934 _refine_diff_density_rms 0.131