# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Yihua Zhang' _publ_contact_author_email ZYHTGD@SOHU.COM _publ_section_title ; Nanometer-size Titanium Dioxide Catalyzed Reactions of Nitric Oxide with Aliphatic Cyclic and Aromatic Amines ; loop_ _publ_author_name 'Yihua Zhang' 'Fengqi Cao' 'Ye Ding' 'Lei Fang' 'Zhangjian Huang' ; Yisheng Lai ; 'Sixun Peng' 'Zhiguo Zhang' 'Ji Zhang' # Attachment '3i.CIF' data_y _database_code_depnum_ccdc_archive 'CCDC 705768' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Hydrochloride salt of O2-Methyl 1-(4-benzylpiperazin-1- yl)diazen-1-ium-1,2-diolate ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H19 Cl N4 O2' _chemical_formula_sum 'C12 H19 Cl N4 O2' _chemical_formula_weight 286.76 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 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 7.0760(14) _cell_length_b 9.0240(18) _cell_length_c 22.863(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.14(3) _cell_angle_gamma 90.00 _cell_volume 1451.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9240 _exptl_absorpt_correction_T_max 0.9737 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 0 _diffrn_reflns_number 2845 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.26 _reflns_number_total 2633 _reflns_number_gt 1972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.1000P)^2^+2.2200P] 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 2633 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1915 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Cl Cl 1.19467(12) 0.42284(10) 0.73602(4) 0.0445(3) Uani 1 1 d . . . O1 O 0.6773(5) 0.6871(3) 0.55617(13) 0.0621(8) Uani 1 1 d . . . O2 O 0.7448(4) 0.5231(4) 0.47435(12) 0.0583(8) Uani 1 1 d . . . N1 N 0.7617(4) 0.3954(3) 0.73935(12) 0.0310(6) Uani 1 1 d . . . N2 N 0.6733(4) 0.4968(3) 0.62114(12) 0.0388(7) Uani 1 1 d . . . N3 N 0.7013(4) 0.5521(3) 0.56470(13) 0.0410(7) Uani 1 1 d . . . N4 N 0.7445(5) 0.4546(4) 0.52787(13) 0.0480(8) Uani 1 1 d . . . C1 C 0.6762(10) 0.5947(7) 0.9250(2) 0.094(2) Uani 1 1 d . . . H1A H 0.5838 0.6432 0.9439 0.113 Uiso 1 1 calc R . . C2 C 0.6211(7) 0.5053(6) 0.87668(19) 0.0683(13) Uani 1 1 d . . . H2A H 0.4930 0.4934 0.8636 0.082 Uiso 1 1 calc R . . C3 C 0.7584(5) 0.4342(4) 0.84827(15) 0.0385(8) Uani 1 1 d . . . C4 C 0.9473(6) 0.4516(5) 0.86941(17) 0.0532(10) Uani 1 1 d . . . H4B H 1.0403 0.4030 0.8509 0.064 Uiso 1 1 calc R . . C5 C 1.0005(7) 0.5406(6) 0.9180(2) 0.0666(13) Uani 1 1 d . . . H5A H 1.1280 0.5516 0.9321 0.080 Uiso 1 1 calc R . . C6 C 0.8610(10) 0.6124(6) 0.9451(2) 0.0835(18) Uani 1 1 d . . . H6A H 0.8948 0.6733 0.9774 0.100 Uiso 1 1 calc R . . C7 C 0.7018(5) 0.3371(4) 0.79609(15) 0.0400(8) Uani 1 1 d . . . H7A H 0.5647 0.3257 0.7918 0.048 Uiso 1 1 calc R . . H7B H 0.7573 0.2397 0.8035 0.048 Uiso 1 1 calc R . . C8 C 0.6892(5) 0.5482(3) 0.72571(15) 0.0349(8) Uani 1 1 d . . . H8A H 0.7391 0.6155 0.7567 0.042 Uiso 1 1 calc R . . H8B H 0.5516 0.5489 0.7240 0.042 Uiso 1 1 calc R . . C9 C 0.7488(5) 0.5998(4) 0.66754(15) 0.0367(8) Uani 1 1 d . . . H9A H 0.7003 0.6988 0.6587 0.044 Uiso 1 1 calc R . . H9B H 0.8864 0.6030 0.6696 0.044 Uiso 1 1 calc R . . C10 C 0.7516(5) 0.3468(4) 0.63185(16) 0.0413(8) Uani 1 1 d . . . H10A H 0.8892 0.3490 0.6335 0.050 Uiso 1 1 calc R . . H10B H 0.7028 0.2805 0.6004 0.050 Uiso 1 1 calc R . . C11 C 0.6918(5) 0.2935(4) 0.69025(15) 0.0411(8) Uani 1 1 d . . . H11A H 0.5543 0.2876 0.6875 0.049 Uiso 1 1 calc R . . H11B H 0.7423 0.1949 0.6986 0.049 Uiso 1 1 calc R . . C12 C 0.7886(7) 0.4128(6) 0.43293(19) 0.0672(13) Uani 1 1 d . . . H12A H 0.7882 0.4570 0.3947 0.101 Uiso 1 1 calc R . . H12B H 0.6951 0.3354 0.4314 0.101 Uiso 1 1 calc R . . H12C H 0.9119 0.3719 0.4449 0.101 Uiso 1 1 calc R . . H H 0.905(7) 0.397(5) 0.741(2) 0.081 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 Cl 0.0322(5) 0.0384(5) 0.0630(6) 0.0045(4) 0.0053(4) 0.0005(3) O1 0.089(2) 0.0430(17) 0.0550(17) 0.0108(14) 0.0120(15) 0.0047(15) O2 0.0616(18) 0.069(2) 0.0450(15) -0.0003(14) 0.0112(13) -0.0010(15) N1 0.0262(13) 0.0216(13) 0.0453(16) -0.0008(11) 0.0051(11) -0.0011(10) N2 0.0469(16) 0.0293(15) 0.0396(16) -0.0008(13) 0.0020(12) 0.0013(13) N3 0.0396(16) 0.0422(18) 0.0416(17) 0.0013(14) 0.0067(13) -0.0035(13) N4 0.057(2) 0.052(2) 0.0356(16) -0.0013(15) 0.0070(14) 0.0005(16) C1 0.130(5) 0.100(4) 0.050(3) -0.014(3) -0.001(3) 0.069(4) C2 0.076(3) 0.075(3) 0.054(3) 0.000(2) 0.003(2) 0.039(3) C3 0.0474(19) 0.0308(17) 0.0373(18) 0.0083(15) 0.0046(15) 0.0038(15) C4 0.064(3) 0.050(2) 0.046(2) 0.0003(18) 0.0081(18) -0.006(2) C5 0.081(3) 0.062(3) 0.054(3) 0.005(2) -0.006(2) -0.021(2) C6 0.147(6) 0.057(3) 0.043(3) -0.006(2) -0.008(3) 0.018(3) C7 0.0392(18) 0.0334(19) 0.048(2) 0.0063(15) 0.0076(15) -0.0074(15) C8 0.0347(17) 0.0204(16) 0.050(2) 0.0001(14) 0.0052(14) 0.0016(13) C9 0.0388(18) 0.0245(16) 0.046(2) -0.0001(14) 0.0029(15) 0.0001(14) C10 0.048(2) 0.0265(18) 0.048(2) -0.0078(15) 0.0014(16) 0.0002(15) C11 0.047(2) 0.0256(17) 0.050(2) -0.0042(15) 0.0023(16) -0.0052(15) C12 0.067(3) 0.088(4) 0.046(2) -0.018(2) 0.008(2) 0.007(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 N3 1.242(4) . ? O2 N4 1.371(4) . ? O2 C12 1.431(5) . ? N1 C8 1.493(4) . ? N1 C11 1.494(4) . ? N1 C7 1.502(4) . ? N1 H 1.01(5) . ? N2 N3 1.417(4) . ? N2 C9 1.468(4) . ? N2 C10 1.473(4) . ? N3 N4 1.277(4) . ? C1 C6 1.349(9) . ? C1 C2 1.390(8) . ? C1 H1A 0.9300 . ? C2 C3 1.383(5) . ? C2 H2A 0.9300 . ? C3 C4 1.380(6) . ? C3 C7 1.500(5) . ? C4 C5 1.390(6) . ? C4 H4B 0.9300 . ? C5 C6 1.382(8) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.511(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 N4 O2 C12 107.3(3) . . ? C8 N1 C11 109.5(3) . . ? C8 N1 C7 112.4(3) . . ? C11 N1 C7 109.4(3) . . ? C8 N1 H 108(3) . . ? C11 N1 H 107(3) . . ? C7 N1 H 110(3) . . ? N3 N2 C9 111.1(3) . . ? N3 N2 C10 112.8(3) . . ? C9 N2 C10 111.1(3) . . ? O1 N3 N4 127.6(3) . . ? O1 N3 N2 117.2(3) . . ? N4 N3 N2 115.1(3) . . ? N3 N4 O2 107.5(3) . . ? C6 C1 C2 121.3(5) . . ? C6 C1 H1A 119.4 . . ? C2 C1 H1A 119.4 . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C4 C3 C2 119.0(4) . . ? C4 C3 C7 120.7(3) . . ? C2 C3 C7 120.2(4) . . ? C3 C4 C5 121.0(4) . . ? C3 C4 H4B 119.5 . . ? C5 C4 H4B 119.5 . . ? C6 C5 C4 119.0(5) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C1 C6 C5 120.3(5) . . ? C1 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C3 C7 N1 114.0(3) . . ? C3 C7 H7A 108.8 . . ? N1 C7 H7A 108.8 . . ? C3 C7 H7B 108.8 . . ? N1 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N1 C8 C9 110.3(3) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C8 109.1(3) . . ? N2 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? N2 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N2 C10 C11 107.5(3) . . ? N2 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? N2 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N1 C11 C10 111.3(3) . . ? N1 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? N1 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C9 N2 N3 O1 -39.6(4) . . . . ? C10 N2 N3 O1 -165.2(3) . . . . ? C9 N2 N3 N4 142.0(3) . . . . ? C10 N2 N3 N4 16.5(4) . . . . ? O1 N3 N4 O2 -5.0(5) . . . . ? N2 N3 N4 O2 173.2(3) . . . . ? C12 O2 N4 N3 -178.6(3) . . . . ? C6 C1 C2 C3 -0.6(9) . . . . ? C1 C2 C3 C4 1.3(7) . . . . ? C1 C2 C3 C7 179.9(4) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C7 C3 C4 C5 -179.5(4) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C2 C1 C6 C5 -0.4(9) . . . . ? C4 C5 C6 C1 0.8(8) . . . . ? C4 C3 C7 N1 -67.8(4) . . . . ? C2 C3 C7 N1 113.6(4) . . . . ? C8 N1 C7 C3 -56.0(4) . . . . ? C11 N1 C7 C3 -177.9(3) . . . . ? C11 N1 C8 C9 -56.7(3) . . . . ? C7 N1 C8 C9 -178.5(3) . . . . ? N3 N2 C9 C8 171.3(3) . . . . ? C10 N2 C9 C8 -62.2(4) . . . . ? N1 C8 C9 N2 59.0(3) . . . . ? N3 N2 C10 C11 -173.3(3) . . . . ? C9 N2 C10 C11 61.2(4) . . . . ? C8 N1 C11 C10 57.2(4) . . . . ? C7 N1 C11 C10 -179.2(3) . . . . ? N2 C10 C11 N1 -58.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.26 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.353 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.088 # Attachment '6a.CIF' data_z _database_code_depnum_ccdc_archive 'CCDC 705769' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "N-Methoxy-N'-p-methoxyphenyldiimide N'-oxide" _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N2 O3' _chemical_formula_sum 'C16 H20 N4 O6' _chemical_formula_weight 364.36 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 Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 11.553(2) _cell_length_b 21.960(4) _cell_length_c 6.9610(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1766.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 0 _diffrn_reflns_number 3441 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.30 _reflns_number_total 1747 _reflns_number_gt 940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.0800P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 1747 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1620 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 O1 O 0.6309(3) 0.90781(16) 0.9391(8) 0.0672(17) Uani 1 1 d . . . O2 O 0.5072(3) 0.63183(16) 0.9898(11) 0.0931(18) Uani 1 1 d . . . O3 O 0.6786(3) 0.56556(15) 0.9881(10) 0.0703(13) Uani 1 1 d . . . N1 N 0.6066(4) 0.6550(2) 0.9791(11) 0.0550(15) Uani 1 1 d . . . N2 N 0.7018(4) 0.62664(18) 0.9777(9) 0.0594(14) Uani 1 1 d . . . C1 C 0.7381(5) 0.9386(2) 0.9740(17) 0.079(2) Uani 1 1 d . . . H1A H 0.7270 0.9817 0.9603 0.118 Uiso 1 1 calc R . . H1B H 0.7949 0.9249 0.8832 0.118 Uiso 1 1 calc R . . H1C H 0.7641 0.9297 1.1019 0.118 Uiso 1 1 calc R . . C2 C 0.6310(5) 0.8461(3) 0.9519(10) 0.0462(18) Uani 1 1 d . . . C3 C 0.5303(5) 0.8170(3) 0.8988(10) 0.0584(17) Uani 1 1 d . . . H3A H 0.4674 0.8397 0.8562 0.070 Uiso 1 1 calc R . . C4 C 0.5222(6) 0.7538(2) 0.9085(12) 0.0460(17) Uani 1 1 d . . . H4A H 0.4541 0.7342 0.8734 0.055 Uiso 1 1 calc R . . C5 C 0.6165(4) 0.7208(2) 0.9708(10) 0.0457(15) Uani 1 1 d . . . C6 C 0.7170(6) 0.7493(2) 1.0290(11) 0.0435(17) Uani 1 1 d . . . H6A H 0.7780 0.7266 1.0786 0.052 Uiso 1 1 calc R . . C7 C 0.7265(4) 0.8123(2) 1.0129(11) 0.0510(16) Uani 1 1 d . . . H7A H 0.7958 0.8317 1.0425 0.061 Uiso 1 1 calc R . . C8 C 0.7872(5) 0.5338(2) 0.9789(16) 0.085(2) Uani 1 1 d . . . H8A H 0.7737 0.4908 0.9869 0.127 Uiso 1 1 calc R . . H8B H 0.8354 0.5464 1.0841 0.127 Uiso 1 1 calc R . . H8C H 0.8251 0.5431 0.8597 0.127 Uiso 1 1 calc R . . O4 O 0.6207(3) 0.09438(16) 0.9664(10) 0.0670(14) Uani 1 1 d . . . O5 O 0.7463(3) 0.37166(15) 0.9825(10) 0.0773(15) Uani 1 1 d . . . O6 O 0.5727(3) 0.43613(15) 0.9927(12) 0.0729(14) Uani 1 1 d . . . N3 N 0.6469(4) 0.3473(2) 0.9804(9) 0.0504(14) Uani 1 1 d . . . N4 N 0.5515(4) 0.3748(2) 0.9890(11) 0.0647(15) Uani 1 1 d . . . C9 C 0.5138(5) 0.0648(2) 0.9360(14) 0.085(3) Uani 1 1 d . . . H9A H 0.5248 0.0215 0.9426 0.127 Uiso 1 1 calc R . . H9B H 0.4843 0.0755 0.8116 0.127 Uiso 1 1 calc R . . H9C H 0.4597 0.0772 1.0330 0.127 Uiso 1 1 calc R . . C10 C 0.6236(5) 0.1569(2) 0.9636(12) 0.0477(18) Uani 1 1 d . . . C11 C 0.7237(4) 0.1839(2) 1.0183(12) 0.0526(17) Uani 1 1 d . . . H11A H 0.7869 0.1600 1.0520 0.063 Uiso 1 1 calc R . . C12 C 0.7330(6) 0.2467(2) 1.0248(13) 0.0508(19) Uani 1 1 d . . . H12A H 0.8012 0.2654 1.0643 0.061 Uiso 1 1 calc R . . C13 C 0.6388(4) 0.2805(2) 0.9712(10) 0.0459(15) Uani 1 1 d . . . C14 C 0.5377(6) 0.2548(2) 0.9098(12) 0.0474(18) Uani 1 1 d . . . H14A H 0.4758 0.2791 0.8720 0.057 Uiso 1 1 calc R . . C15 C 0.5287(5) 0.1915(2) 0.9046(10) 0.0502(16) Uani 1 1 d . . . H15A H 0.4610 0.1728 0.8628 0.060 Uiso 1 1 calc R . . C16 C 0.4626(5) 0.4669(3) 0.9956(18) 0.092(3) Uani 1 1 d . . . H16A H 0.4748 0.5101 0.9968 0.138 Uiso 1 1 calc R . . H16B H 0.4204 0.4551 1.1085 0.138 Uiso 1 1 calc R . . H16C H 0.4190 0.4559 0.8834 0.138 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 0.057(2) 0.047(2) 0.097(5) 0.002(3) 0.000(3) 0.007(2) O2 0.044(2) 0.066(3) 0.170(6) 0.002(5) 0.006(4) -0.0121(19) O3 0.067(3) 0.042(2) 0.102(4) -0.004(3) -0.002(4) -0.006(2) N1 0.038(2) 0.055(3) 0.072(4) -0.008(4) 0.003(3) -0.006(2) N2 0.054(3) 0.049(3) 0.075(4) 0.003(4) 0.001(4) 0.001(2) C1 0.071(4) 0.052(3) 0.113(6) 0.002(5) -0.004(6) 0.004(3) C2 0.039(3) 0.051(3) 0.049(5) 0.003(3) -0.001(3) 0.008(3) C3 0.046(3) 0.069(4) 0.060(4) 0.004(4) -0.007(3) 0.005(3) C4 0.029(3) 0.060(4) 0.049(4) 0.000(3) 0.000(4) -0.004(2) C5 0.042(3) 0.052(3) 0.043(4) -0.006(4) 0.007(4) 0.001(3) C6 0.040(4) 0.050(3) 0.040(5) 0.003(3) -0.009(4) 0.002(2) C7 0.044(3) 0.049(3) 0.060(5) -0.003(4) -0.007(3) -0.004(2) C8 0.069(4) 0.057(4) 0.128(7) -0.006(6) -0.005(6) 0.007(3) O4 0.050(2) 0.053(2) 0.098(4) -0.002(3) -0.003(3) 0.0016(19) O5 0.048(2) 0.059(2) 0.125(4) -0.013(4) -0.007(3) -0.0076(19) O6 0.057(3) 0.043(2) 0.119(4) 0.000(3) 0.003(4) -0.0031(19) N3 0.042(3) 0.049(2) 0.060(4) 0.000(3) 0.002(4) -0.003(2) N4 0.052(3) 0.052(3) 0.091(4) -0.004(4) 0.007(4) 0.003(2) C9 0.069(5) 0.051(3) 0.135(10) -0.004(5) 0.003(5) -0.011(3) C10 0.049(4) 0.040(3) 0.054(5) 0.000(4) 0.003(3) 0.003(2) C11 0.041(3) 0.049(3) 0.067(5) 0.001(4) 0.000(3) 0.005(3) C12 0.036(4) 0.062(4) 0.055(5) 0.004(4) -0.006(4) -0.005(2) C13 0.041(3) 0.052(3) 0.045(4) 0.000(4) 0.000(4) -0.004(3) C14 0.035(4) 0.051(3) 0.056(5) -0.004(3) 0.002(4) 0.006(2) C15 0.043(3) 0.051(3) 0.056(4) -0.008(3) -0.002(3) -0.003(3) C16 0.064(4) 0.060(4) 0.151(8) 0.005(6) 0.008(6) 0.011(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 C2 1.358(6) . ? O1 C1 1.431(7) . ? O2 N1 1.259(5) . ? O3 N2 1.370(5) . ? O3 C8 1.437(6) . ? N1 N2 1.264(6) . ? N1 C5 1.451(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.378(8) . ? C2 C7 1.396(7) . ? C3 C4 1.392(7) . ? C3 H3A 0.9300 . ? C4 C5 1.378(8) . ? C4 H4A 0.9300 . ? C5 C6 1.380(8) . ? C6 C7 1.392(6) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O4 C10 1.373(6) . ? O4 C9 1.412(6) . ? O5 N3 1.266(5) . ? O6 N4 1.369(5) . ? O6 C16 1.440(6) . ? N3 N4 1.259(5) . ? N3 C13 1.471(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.355(8) . ? C10 C15 1.396(8) . ? C11 C12 1.383(7) . ? C11 H11A 0.9300 . ? C12 C13 1.369(8) . ? C12 H12A 0.9300 . ? C13 C14 1.367(8) . ? C14 C15 1.393(7) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 O1 C1 117.4(5) . . ? N2 O3 C8 107.5(4) . . ? O2 N1 N2 126.6(5) . . ? O2 N1 C5 118.5(5) . . ? N2 N1 C5 115.0(4) . . ? N1 N2 O3 108.1(4) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 116.5(5) . . ? O1 C2 C7 123.4(5) . . ? C3 C2 C7 120.1(5) . . ? C2 C3 C4 120.5(6) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 119.0(6) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 121.3(5) . . ? C4 C5 N1 118.3(5) . . ? C6 C5 N1 120.4(5) . . ? C5 C6 C7 119.5(5) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C6 C7 C2 119.4(5) . . ? C6 C7 H7A 120.3 . . ? C2 C7 H7A 120.3 . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 O4 C9 118.6(5) . . ? N4 O6 C16 107.7(4) . . ? N4 N3 O5 126.2(4) . . ? N4 N3 C13 115.1(4) . . ? O5 N3 C13 118.7(4) . . ? N3 N4 O6 108.5(4) . . ? O4 C9 H9A 109.5 . . ? O4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 O4 117.1(5) . . ? C11 C10 C15 120.9(5) . . ? O4 C10 C15 122.0(5) . . ? C10 C11 C12 120.8(5) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C13 C12 C11 118.0(6) . . ? C13 C12 H12A 121.0 . . ? C11 C12 H12A 121.0 . . ? C14 C13 C12 122.7(5) . . ? C14 C13 N3 118.8(5) . . ? C12 C13 N3 118.6(5) . . ? C13 C14 C15 119.0(6) . . ? C13 C14 H14A 120.5 . . ? C15 C14 H14A 120.5 . . ? C14 C15 C10 118.5(5) . . ? C14 C15 H15A 120.7 . . ? C10 C15 H15A 120.7 . . ? O6 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 N1 N2 O3 0.6(12) . . . . ? C5 N1 N2 O3 179.4(7) . . . . ? C8 O3 N2 N1 177.8(8) . . . . ? C1 O1 C2 C3 -173.6(7) . . . . ? C1 O1 C2 C7 5.7(12) . . . . ? O1 C2 C3 C4 -179.6(6) . . . . ? C7 C2 C3 C4 1.1(11) . . . . ? C2 C3 C4 C5 -0.4(11) . . . . ? C3 C4 C5 C6 2.0(11) . . . . ? C3 C4 C5 N1 -179.7(7) . . . . ? O2 N1 C5 C4 -22.3(11) . . . . ? N2 N1 C5 C4 158.8(7) . . . . ? O2 N1 C5 C6 156.0(8) . . . . ? N2 N1 C5 C6 -22.9(11) . . . . ? C4 C5 C6 C7 -4.3(11) . . . . ? N1 C5 C6 C7 177.5(7) . . . . ? C5 C6 C7 C2 4.9(11) . . . . ? O1 C2 C7 C6 177.4(7) . . . . ? C3 C2 C7 C6 -3.3(11) . . . . ? O5 N3 N4 O6 2.6(11) . . . . ? C13 N3 N4 O6 -178.8(7) . . . . ? C16 O6 N4 N3 178.0(8) . . . . ? C9 O4 C10 C11 171.5(7) . . . . ? C9 O4 C10 C15 -9.5(14) . . . . ? O4 C10 C11 C12 -178.2(8) . . . . ? C15 C10 C11 C12 2.7(13) . . . . ? C10 C11 C12 C13 -1.1(12) . . . . ? C11 C12 C13 C14 -0.9(13) . . . . ? C11 C12 C13 N3 179.1(7) . . . . ? N4 N3 C13 C14 21.4(10) . . . . ? O5 N3 C13 C14 -159.9(7) . . . . ? N4 N3 C13 C12 -158.6(7) . . . . ? O5 N3 C13 C12 20.1(11) . . . . ? C12 C13 C14 C15 1.3(12) . . . . ? N3 C13 C14 C15 -178.7(6) . . . . ? C13 C14 C15 C10 0.3(11) . . . . ? C11 C10 C15 C14 -2.3(11) . . . . ? O4 C10 C15 C14 178.7(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.279 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.041 # Attachment '3h.CIF' data_x _database_code_depnum_ccdc_archive 'CCDC 705770' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'O2-Methyl 1-(4-Phenylpiperazin-1-yl)diazen-1-ium-1,2-diolate' _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 N4 O2' _chemical_formula_sum 'C11 H16 N4 O2' _chemical_formula_weight 236.28 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.638(2) _cell_length_b 7.5620(15) _cell_length_c 30.221(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2431.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 0 _diffrn_reflns_number 2169 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.16 _reflns_number_total 2169 _reflns_number_gt 1116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.0600P)^2^+2.0000P] 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 2169 _refine_ls_number_parameters 154 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.1502 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2105 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.045 _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 1.0073(3) 0.1651(5) 0.13257(11) 0.0859(10) Uani 1 1 d . . . O1 O 0.8638(3) 0.6696(5) 0.03826(11) 0.1322(14) Uani 1 1 d . . . C1 C 1.0159(6) -0.2692(7) 0.22145(17) 0.1113(16) Uani 1 1 d U . . H1A H 1.0188 -0.3624 0.2415 0.134 Uiso 1 1 calc R . . O2 O 1.0414(3) 0.8626(4) 0.03426(9) 0.0914(9) Uani 1 1 d . . . N2 N 0.9480(3) 0.4937(4) 0.09331(11) 0.0806(10) Uani 1 1 d . . . C2 C 0.9101(5) -0.2365(8) 0.19808(17) 0.1141(16) Uani 1 1 d U . . H2A H 0.8395 -0.3076 0.2020 0.137 Uiso 1 1 calc R . . N3 N 0.9589(4) 0.6360(5) 0.06270(11) 0.0866(10) Uani 1 1 d . . . C3 C 0.9068(5) -0.0992(6) 0.16878(15) 0.0976(13) Uani 1 1 d U . . H3A H 0.8330 -0.0809 0.1529 0.117 Uiso 1 1 calc R . . N4 N 1.0574(3) 0.7289(5) 0.06304(11) 0.0878(10) Uani 1 1 d . . . C4 C 1.0063(4) 0.0146(6) 0.16114(13) 0.0787(11) Uani 1 1 d U . . C5 C 1.1154(4) -0.0266(6) 0.18536(15) 0.0923(13) Uani 1 1 d U . . H5A H 1.1867 0.0419 0.1806 0.111 Uiso 1 1 calc R . . C6 C 1.1228(5) -0.1588(7) 0.21491(15) 0.1062(15) Uani 1 1 d U . . H6A H 1.1964 -0.1780 0.2308 0.127 Uiso 1 1 calc R . . C7 C 0.8945(4) 0.1892(7) 0.10436(15) 0.1025(15) Uani 1 1 d . . . H7A H 0.8232 0.2223 0.1226 0.123 Uiso 1 1 calc R . . H7B H 0.8744 0.0789 0.0896 0.123 Uiso 1 1 calc R . . C8 C 0.9192(4) 0.3337(6) 0.06982(14) 0.0935(14) Uani 1 1 d . . . H8A H 0.9891 0.3003 0.0510 0.112 Uiso 1 1 calc R . . H8B H 0.8455 0.3505 0.0514 0.112 Uiso 1 1 calc R . . C9 C 1.0635(4) 0.4672(7) 0.11909(14) 0.1004(15) Uani 1 1 d . . . H9A H 1.0875 0.5764 0.1336 0.121 Uiso 1 1 calc R . . H9B H 1.1316 0.4311 0.0997 0.121 Uiso 1 1 calc R . . C10 C 1.0381(4) 0.3242(6) 0.15337(14) 0.0896(13) Uani 1 1 d . . . H10A H 1.1121 0.3075 0.1717 0.108 Uiso 1 1 calc R . . H10B H 0.9694 0.3607 0.1724 0.108 Uiso 1 1 calc R . . C11 C 1.1578(4) 0.9723(8) 0.03524(15) 0.1182(18) Uani 1 1 d . . . H11A H 1.1478 1.0721 0.0159 0.177 Uiso 1 1 calc R . . H11B H 1.2279 0.9024 0.0256 0.177 Uiso 1 1 calc R . . H11C H 1.1726 1.0130 0.0649 0.177 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 0.080(2) 0.114(3) 0.0638(19) -0.001(2) -0.0008(17) 0.005(2) O1 0.093(2) 0.194(4) 0.110(3) 0.048(3) -0.033(2) -0.017(2) C1 0.145(4) 0.101(3) 0.089(3) 0.022(3) 0.024(3) 0.005(3) O2 0.099(2) 0.103(2) 0.0717(17) 0.0113(18) -0.0061(16) 0.0062(17) N2 0.082(2) 0.091(2) 0.0685(19) 0.006(2) 0.0018(17) -0.0004(19) C2 0.126(4) 0.120(3) 0.095(3) 0.006(3) 0.022(3) -0.013(3) N3 0.096(3) 0.093(2) 0.071(2) 0.004(2) -0.001(2) 0.014(2) C3 0.102(3) 0.103(3) 0.088(3) 0.011(3) 0.021(3) 0.009(3) N4 0.076(2) 0.119(3) 0.069(2) 0.009(2) -0.0043(18) 0.001(2) C4 0.082(3) 0.097(3) 0.057(2) -0.016(2) 0.0150(19) -0.005(2) C5 0.097(3) 0.096(3) 0.084(3) -0.004(3) 0.004(2) 0.006(3) C6 0.123(4) 0.123(4) 0.073(3) -0.003(3) 0.009(3) 0.004(3) C7 0.097(3) 0.125(4) 0.085(3) 0.001(3) -0.004(3) -0.002(3) C8 0.102(3) 0.100(3) 0.079(3) -0.022(3) -0.019(2) 0.017(3) C9 0.109(3) 0.125(4) 0.067(2) 0.021(3) -0.022(2) -0.011(3) C10 0.104(3) 0.097(3) 0.068(2) -0.008(3) -0.008(2) -0.008(3) C11 0.101(3) 0.173(5) 0.080(3) -0.015(4) 0.009(3) -0.012(4) _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 C10 1.396(5) . ? N1 C4 1.428(5) . ? N1 C7 1.483(5) . ? O1 N3 1.278(4) . ? C1 C2 1.352(7) . ? C1 C6 1.425(7) . ? C1 H1A 0.9300 . ? O2 N4 1.345(4) . ? O2 C11 1.490(5) . ? N2 N3 1.423(4) . ? N2 C8 1.436(5) . ? N2 C9 1.469(5) . ? C2 C3 1.366(6) . ? C2 H2A 0.9300 . ? N3 N4 1.261(5) . ? C3 C4 1.384(6) . ? C3 H3A 0.9300 . ? C4 C5 1.407(6) . ? C5 C6 1.343(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.534(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.522(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 C10 N1 C4 114.6(3) . . ? C10 N1 C7 110.0(4) . . ? C4 N1 C7 116.1(4) . . ? C2 C1 C6 119.0(5) . . ? C2 C1 H1A 120.5 . . ? C6 C1 H1A 120.5 . . ? N4 O2 C11 107.5(3) . . ? N3 N2 C8 109.4(3) . . ? N3 N2 C9 112.3(3) . . ? C8 N2 C9 109.0(3) . . ? C1 C2 C3 119.9(5) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? N4 N3 O1 123.4(4) . . ? N4 N3 N2 118.9(4) . . ? O1 N3 N2 117.5(4) . . ? C2 C3 C4 124.2(5) . . ? C2 C3 H3A 117.9 . . ? C4 C3 H3A 117.9 . . ? N3 N4 O2 108.0(3) . . ? C3 C4 C5 114.0(4) . . ? C3 C4 N1 127.0(4) . . ? C5 C4 N1 119.0(4) . . ? C6 C5 C4 124.0(5) . . ? C6 C5 H5A 118.0 . . ? C4 C5 H5A 118.0 . . ? C5 C6 C1 118.8(5) . . ? C5 C6 H6A 120.6 . . ? C1 C6 H6A 120.6 . . ? N1 C7 C8 109.9(4) . . ? N1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N2 C8 C7 107.5(3) . . ? N2 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? N2 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N2 C9 C10 108.0(4) . . ? N2 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? N2 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N1 C10 C9 110.3(3) . . ? N1 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N1 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 C6 C1 C2 C3 -0.1(8) . . . . ? C8 N2 N3 N4 -126.4(4) . . . . ? C9 N2 N3 N4 -5.2(5) . . . . ? C8 N2 N3 O1 58.2(5) . . . . ? C9 N2 N3 O1 179.4(4) . . . . ? C1 C2 C3 C4 -0.7(7) . . . . ? O1 N3 N4 O2 0.3(5) . . . . ? N2 N3 N4 O2 -174.7(3) . . . . ? C11 O2 N4 N3 179.5(3) . . . . ? C2 C3 C4 C5 2.1(6) . . . . ? C2 C3 C4 N1 -176.9(4) . . . . ? C10 N1 C4 C3 122.5(5) . . . . ? C7 N1 C4 C3 -7.6(6) . . . . ? C10 N1 C4 C5 -56.5(5) . . . . ? C7 N1 C4 C5 173.4(4) . . . . ? C3 C4 C5 C6 -2.9(6) . . . . ? N1 C4 C5 C6 176.2(4) . . . . ? C4 C5 C6 C1 2.2(7) . . . . ? C2 C1 C6 C5 -0.6(7) . . . . ? C10 N1 C7 C8 58.3(4) . . . . ? C4 N1 C7 C8 -169.5(3) . . . . ? N3 N2 C8 C7 -174.0(3) . . . . ? C9 N2 C8 C7 62.8(4) . . . . ? N1 C7 C8 N2 -59.5(5) . . . . ? N3 N2 C9 C10 175.0(3) . . . . ? C8 N2 C9 C10 -63.5(4) . . . . ? C4 N1 C10 C9 168.0(4) . . . . ? C7 N1 C10 C9 -59.0(5) . . . . ? N2 C9 C10 N1 61.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.146 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.041