Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_TNBADN _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1:1 Molecular complex of TNB and Acridene ; _chemical_name_common 'Complex of TNB and Acridene' _chemical_melting_point ? _chemical_formula_moiety 'C19 H12 N4 O6' _chemical_formula_sum 'C19 H12 N4 O6' _chemical_formula_weight 392.33 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 11.741(2) _cell_length_b 12.828(3) _cell_length_c 12.047(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.46(3) _cell_angle_gamma 90.00 _cell_volume 1721.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 18.0 _exptl_crystal_description needels _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.116 _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 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius FAST area detector' _diffrn_measurement_method 'box integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3940 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3940 _reflns_number_gt 2800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MADNES-Messerschmidt & Pflugrath' _computing_cell_refinement 'MADNES-Messerschmidt & Pflugrath' _computing_data_reduction 'MADNES-Messerschmidt & Pflugrath' _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^)+(0.0365P)^2^+3.5955P] 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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3940 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O6 O 0.13883(18) 0.08715(16) 0.54351(18) 0.0299(5) Uani 1 1 d . . . O2 O -0.26185(18) 0.47049(16) 0.59487(18) 0.0321(5) Uani 1 1 d . . . O5 O 0.17305(18) 0.25033(17) 0.51727(18) 0.0326(5) Uani 1 1 d . . . O4 O -0.1930(2) -0.00528(16) 0.6787(2) 0.0353(5) Uani 1 1 d . . . N4 N 0.11445(19) 0.18015(19) 0.54195(19) 0.0231(5) Uani 1 1 d . . . N2 N -0.1606(2) 0.45092(18) 0.5922(2) 0.0262(5) Uani 1 1 d . . . C17 C -0.0588(2) 0.1329(2) 0.6040(2) 0.0189(5) Uani 1 1 d . . . H17A H -0.0372 0.0630 0.6053 0.023 Uiso 1 1 calc R . . C15 C -0.1945(2) 0.2676(2) 0.6302(2) 0.0202(5) Uani 1 1 d . . . H15A H -0.2625 0.2867 0.6490 0.024 Uiso 1 1 calc R . . C16 C -0.1588(2) 0.1647(2) 0.6330(2) 0.0209(5) Uani 1 1 d . . . O3 O -0.32602(18) 0.11240(17) 0.6813(2) 0.0348(5) Uani 1 1 d . . . O1 O -0.0871(2) 0.51627(17) 0.5847(2) 0.0442(6) Uani 1 1 d . . . N3 N -0.2312(2) 0.08411(19) 0.6667(2) 0.0263(5) Uani 1 1 d . . . C19 C -0.0216(2) 0.3149(2) 0.5700(2) 0.0199(5) Uani 1 1 d . . . H19A H 0.0253 0.3655 0.5502 0.024 Uiso 1 1 calc R . . C18 C 0.0070(2) 0.2103(2) 0.5731(2) 0.0194(5) Uani 1 1 d . . . C14 C -0.1245(2) 0.3406(2) 0.5982(2) 0.0206(5) Uani 1 1 d . . . C12 C 0.0935(2) 0.2185(2) 0.8769(2) 0.0179(5) Uani 1 1 d . . . N1 N 0.18259(19) 0.16900(17) 0.84933(18) 0.0198(4) Uani 1 1 d . . . C11 C 0.0798(2) 0.3299(2) 0.8723(2) 0.0177(5) Uani 1 1 d . . . C10 C 0.2612(2) 0.2278(2) 0.8160(2) 0.0187(5) Uani 1 1 d . . . C13 C 0.1615(2) 0.3884(2) 0.8362(2) 0.0204(5) Uani 1 1 d . . . H13A H 0.1546 0.4606 0.8320 0.025 Uiso 1 1 calc R . . C8 C -0.0174(2) 0.3754(2) 0.9023(2) 0.0226(5) Uani 1 1 d . . . H8A H -0.0277 0.4473 0.8986 0.027 Uiso 1 1 calc R . . C9 C 0.2537(2) 0.3392(2) 0.8063(2) 0.0210(5) Uani 1 1 d . . . C5 C 0.0094(2) 0.1575(2) 0.9126(2) 0.0233(5) Uani 1 1 d . . . H5A H 0.0167 0.0853 0.9159 0.028 Uiso 1 1 calc R . . C4 C 0.3595(2) 0.1770(2) 0.7920(2) 0.0247(6) Uani 1 1 d . . . H4A H 0.3673 0.1050 0.7997 0.030 Uiso 1 1 calc R . . C1 C 0.3411(2) 0.3943(2) 0.7690(2) 0.0257(6) Uani 1 1 d . . . H1B H 0.3359 0.4664 0.7604 0.031 Uiso 1 1 calc R . . C3 C 0.4412(3) 0.2324(3) 0.7583(2) 0.0302(7) Uani 1 1 d . . . H3A H 0.5043 0.1978 0.7432 0.036 Uiso 1 1 calc R . . C6 C -0.0813(2) 0.2039(2) 0.9420(2) 0.0265(6) Uani 1 1 d . . . H6A H -0.1347 0.1631 0.9659 0.032 Uiso 1 1 calc R . . C2 C 0.4320(3) 0.3417(3) 0.7458(2) 0.0310(7) Uani 1 1 d . . . H2A H 0.4884 0.3782 0.7216 0.037 Uiso 1 1 calc R . . C7 C -0.0952(2) 0.3142(2) 0.9364(2) 0.0278(6) Uani 1 1 d . . . H7A H -0.1580 0.3448 0.9562 0.033 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 O6 0.0275(11) 0.0316(11) 0.0332(11) -0.0018(9) 0.0137(9) 0.0034(9) O2 0.0255(11) 0.0316(11) 0.0378(12) -0.0046(9) 0.0081(9) 0.0068(9) O5 0.0255(11) 0.0386(12) 0.0390(12) 0.0053(9) 0.0179(9) -0.0040(9) O4 0.0398(13) 0.0268(11) 0.0471(13) -0.0012(9) 0.0247(11) -0.0042(9) N4 0.0163(11) 0.0341(13) 0.0190(10) -0.0002(9) 0.0059(9) 0.0008(9) N2 0.0277(13) 0.0256(12) 0.0260(12) -0.0009(9) 0.0093(10) 0.0028(10) C17 0.0132(11) 0.0274(13) 0.0153(11) -0.0004(10) 0.0035(9) -0.0020(10) C15 0.0157(12) 0.0297(14) 0.0142(11) -0.0025(10) 0.0034(9) -0.0014(10) C16 0.0176(12) 0.0277(14) 0.0165(12) -0.0001(10) 0.0042(10) -0.0043(10) O3 0.0224(10) 0.0415(13) 0.0452(13) 0.0045(10) 0.0175(9) -0.0021(9) O1 0.0490(15) 0.0250(11) 0.0690(17) 0.0024(11) 0.0332(13) -0.0042(10) N3 0.0261(12) 0.0303(13) 0.0242(12) -0.0020(10) 0.0102(10) -0.0059(10) C19 0.0155(12) 0.0276(13) 0.0158(11) 0.0005(10) 0.0041(9) -0.0026(10) C18 0.0131(11) 0.0290(13) 0.0142(11) 0.0007(10) 0.0019(9) -0.0007(10) C14 0.0207(13) 0.0243(13) 0.0160(11) -0.0017(10) 0.0046(10) 0.0019(10) C12 0.0135(11) 0.0237(13) 0.0142(11) -0.0003(9) 0.0012(9) -0.0012(10) N1 0.0192(11) 0.0231(11) 0.0162(10) -0.0014(8) 0.0042(8) 0.0014(9) C11 0.0128(11) 0.0229(12) 0.0150(11) -0.0016(9) 0.0009(9) 0.0025(9) C10 0.0149(12) 0.0262(13) 0.0143(11) -0.0041(10) 0.0038(9) -0.0011(10) C13 0.0209(13) 0.0207(12) 0.0180(12) -0.0009(10) 0.0037(10) 0.0023(10) C8 0.0201(13) 0.0255(13) 0.0226(13) -0.0003(10) 0.0075(10) 0.0053(10) C9 0.0168(12) 0.0274(13) 0.0173(12) -0.0017(10) 0.0035(10) -0.0036(10) C5 0.0262(14) 0.0242(13) 0.0191(12) 0.0009(10) 0.0068(10) -0.0014(11) C4 0.0226(13) 0.0292(14) 0.0209(12) -0.0057(11) 0.0049(10) 0.0036(11) C1 0.0237(14) 0.0281(14) 0.0266(14) -0.0047(11) 0.0099(11) -0.0087(11) C3 0.0201(13) 0.0478(18) 0.0259(14) -0.0106(13) 0.0118(11) -0.0007(13) C6 0.0239(14) 0.0359(16) 0.0207(13) 0.0022(11) 0.0085(11) -0.0048(12) C2 0.0213(14) 0.0478(18) 0.0263(14) -0.0073(13) 0.0109(11) -0.0109(13) C7 0.0196(13) 0.0422(17) 0.0233(13) -0.0006(12) 0.0093(11) 0.0035(12) _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 O6 N4 1.226(3) . ? O2 N2 1.225(3) . ? O5 N4 1.226(3) . ? O4 N3 1.223(3) . ? N4 C18 1.477(3) . ? N2 O1 1.227(3) . ? N2 C14 1.472(3) . ? C17 C18 1.380(4) . ? C17 C16 1.388(3) . ? C15 C14 1.379(4) . ? C15 C16 1.382(4) . ? C16 N3 1.475(3) . ? O3 N3 1.235(3) . ? C19 C18 1.380(4) . ? C19 C14 1.393(4) . ? C12 N1 1.351(3) . ? C12 C5 1.430(4) . ? C12 C11 1.437(3) . ? N1 C10 1.348(3) . ? C11 C13 1.391(4) . ? C11 C8 1.427(3) . ? C10 C4 1.432(4) . ? C10 C9 1.434(4) . ? C13 C9 1.395(4) . ? C8 C7 1.363(4) . ? C9 C1 1.431(4) . ? C5 C6 1.361(4) . ? C4 C3 1.355(4) . ? C1 C2 1.364(4) . ? C3 C2 1.411(4) . ? C6 C7 1.423(4) . ? 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 O5 N4 O6 124.9(2) . . ? O5 N4 C18 117.3(2) . . ? O6 N4 C18 117.7(2) . . ? O2 N2 O1 125.0(2) . . ? O2 N2 C14 117.6(2) . . ? O1 N2 C14 117.5(2) . . ? C18 C17 C16 116.5(2) . . ? C14 C15 C16 116.9(2) . . ? C15 C16 C17 123.3(2) . . ? C15 C16 N3 118.6(2) . . ? C17 C16 N3 118.1(2) . . ? O4 N3 O3 124.9(2) . . ? O4 N3 C16 117.9(2) . . ? O3 N3 C16 117.2(2) . . ? C18 C19 C14 116.5(2) . . ? C17 C18 C19 123.7(2) . . ? C17 C18 N4 118.4(2) . . ? C19 C18 N4 117.9(2) . . ? C15 C14 C19 123.1(2) . . ? C15 C14 N2 118.6(2) . . ? C19 C14 N2 118.3(2) . . ? N1 C12 C5 118.6(2) . . ? N1 C12 C11 123.0(2) . . ? C5 C12 C11 118.4(2) . . ? C10 N1 C12 117.8(2) . . ? C13 C11 C8 123.0(2) . . ? C13 C11 C12 117.9(2) . . ? C8 C11 C12 119.1(2) . . ? N1 C10 C4 118.4(2) . . ? N1 C10 C9 123.5(2) . . ? C4 C10 C9 118.0(2) . . ? C11 C13 C9 120.4(2) . . ? C7 C8 C11 120.5(3) . . ? C13 C9 C1 123.4(3) . . ? C13 C9 C10 117.5(2) . . ? C1 C9 C10 119.1(2) . . ? C6 C5 C12 120.7(3) . . ? C3 C4 C10 120.9(3) . . ? C2 C1 C9 120.3(3) . . ? C4 C3 C2 121.0(3) . . ? C5 C6 C7 120.7(3) . . ? C1 C2 C3 120.6(3) . . ? C8 C7 C6 120.6(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.345 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.078 **************************************************************************** data_TNBPNRM _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1:1 Molecular Complex of TNB and 1,10-Phenonthroline ; _chemical_name_common Complex of TNB and phenonthroline _chemical_melting_point ? _chemical_formula_moiety C18 H11 N5 O6 _chemical_formula_sum 'C18 H11 N5 O6' _chemical_formula_weight 393.32 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 ? _symmetry_space_group_name_H-M ? 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 10.962(2) _cell_length_b 13.480(3) _cell_length_c 12.092(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.89(3) _cell_angle_gamma 90.00 _cell_volume 1690.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 10.10 _cell_measurement_theta_max 18.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.120 _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 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 FAST area detector' _diffrn_measurement_method 'box integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3817 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.69 _reflns_number_total 3817 _reflns_number_gt 3210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MADNES-Messerschmidt & Pflugrath' _computing_cell_refinement 'MADNES-Messerschmidt & Pflugrath' _computing_data_reduction 'MADNES-Messerschmidt & Pflugrath' _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^)+(0.0859P)^2^+0.9092P] 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 3817 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.59325(12) 0.14913(9) 0.34461(11) 0.0143(3) Uani 1 1 d . . . N2 N 0.79123(12) 0.21031(9) 0.26534(11) 0.0163(3) Uani 1 1 d . . . C11 C 0.71304(14) 0.28062(10) 0.28851(12) 0.0128(3) Uani 1 1 d . . . C4 C 0.52856(14) 0.32111(10) 0.35671(13) 0.0149(3) Uani 1 1 d . . . C1 C 0.49904(14) 0.12154(11) 0.38552(13) 0.0164(3) Uani 1 1 d . . . H1B H 0.4884 0.0541 0.3957 0.020 Uiso 1 1 calc R . . C12 C 0.60867(13) 0.24831(10) 0.33035(11) 0.0117(3) Uani 1 1 d . . . C7 C 0.73086(14) 0.38407(11) 0.27539(13) 0.0156(3) Uani 1 1 d . . . C2 C 0.41460(14) 0.18794(12) 0.41424(13) 0.0187(3) Uani 1 1 d . . . H2B H 0.3502 0.1648 0.4422 0.022 Uiso 1 1 calc R . . C3 C 0.42991(15) 0.28815(12) 0.39976(14) 0.0190(3) Uani 1 1 d . . . H3A H 0.3758 0.3337 0.4182 0.023 Uiso 1 1 calc R . . C9 C 0.91535(16) 0.34319(13) 0.21827(14) 0.0235(3) Uani 1 1 d . . . H9A H 0.9859 0.3612 0.1961 0.028 Uiso 1 1 calc R . . C10 C 0.88846(16) 0.24229(12) 0.23160(14) 0.0206(3) Uani 1 1 d . . . H10A H 0.9423 0.1950 0.2157 0.025 Uiso 1 1 calc R . . C5 C 0.54838(15) 0.42505(11) 0.33931(14) 0.0200(3) Uani 1 1 d . . . H5A H 0.4944 0.4720 0.3556 0.024 Uiso 1 1 calc R . . C6 C 0.64498(15) 0.45512(11) 0.29937(14) 0.0207(3) Uani 1 1 d . . . H6A H 0.6555 0.5223 0.2875 0.025 Uiso 1 1 calc R . . C8 C 0.83544(16) 0.41412(12) 0.23868(14) 0.0208(3) Uani 1 1 d . . . H8A H 0.8498 0.4810 0.2285 0.025 Uiso 1 1 calc R . . N5 N 0.23452(13) 0.09995(10) 0.14742(12) 0.0202(3) Uani 1 1 d . . . O6 O 0.13796(13) 0.13056(10) 0.16723(13) 0.0329(3) Uani 1 1 d . . . N4 N 0.59802(12) 0.17874(10) 0.00736(11) 0.0182(3) Uani 1 1 d . . . O4 O 0.62674(12) 0.08996(9) 0.01951(11) 0.0267(3) Uani 1 1 d . . . C18 C 0.27667(14) 0.27259(11) 0.10415(13) 0.0154(3) Uani 1 1 d . . . H18A H 0.2074 0.2932 0.1269 0.019 Uiso 1 1 calc R . . C16 C 0.41577(14) 0.13983(11) 0.07665(12) 0.0145(3) Uani 1 1 d . . . H16A H 0.4378 0.0730 0.0803 0.017 Uiso 1 1 calc R . . O1 O 0.22533(12) 0.46909(9) 0.09594(12) 0.0282(3) Uani 1 1 d . . . N3 N 0.31160(13) 0.44540(10) 0.05697(12) 0.0207(3) Uani 1 1 d . . . C15 C 0.48531(13) 0.21126(11) 0.03970(12) 0.0138(3) Uani 1 1 d . . . O5 O 0.27054(13) 0.01327(9) 0.15761(11) 0.0289(3) Uani 1 1 d . . . C14 C 0.45446(14) 0.31194(11) 0.03148(12) 0.0139(3) Uani 1 1 d . . . H14A H 0.5016 0.3581 0.0050 0.017 Uiso 1 1 calc R . . C17 C 0.31183(14) 0.17328(11) 0.10789(12) 0.0149(3) Uani 1 1 d . . . O3 O 0.65612(12) 0.24192(10) -0.02873(12) 0.0283(3) Uani 1 1 d . . . C13 C 0.34955(14) 0.33960(10) 0.06497(13) 0.0152(3) Uani 1 1 d . . . O2 O 0.36769(13) 0.50255(9) 0.01133(14) 0.0352(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0140(6) 0.0126(6) 0.0159(6) 0.0010(4) 0.0044(5) -0.0004(4) N2 0.0161(6) 0.0168(6) 0.0172(6) -0.0013(5) 0.0072(5) -0.0003(5) C11 0.0129(7) 0.0124(7) 0.0113(6) 0.0003(5) 0.0016(5) -0.0003(5) C4 0.0126(7) 0.0135(7) 0.0168(7) -0.0014(5) 0.0022(5) 0.0020(5) C1 0.0173(7) 0.0150(7) 0.0166(7) 0.0021(5) 0.0049(6) -0.0013(5) C12 0.0110(6) 0.0114(6) 0.0109(6) -0.0004(5) 0.0011(5) 0.0012(5) C7 0.0149(7) 0.0142(7) 0.0148(7) 0.0013(5) 0.0008(5) -0.0021(5) C2 0.0143(7) 0.0244(8) 0.0187(7) 0.0004(6) 0.0074(6) -0.0015(6) C3 0.0159(7) 0.0210(7) 0.0208(7) -0.0026(6) 0.0069(6) 0.0036(6) C9 0.0217(8) 0.0287(8) 0.0229(8) 0.0000(6) 0.0113(6) -0.0085(6) C10 0.0198(8) 0.0232(8) 0.0217(7) -0.0031(6) 0.0107(6) -0.0017(6) C5 0.0171(7) 0.0128(7) 0.0273(8) -0.0035(6) 0.0031(6) 0.0032(5) C6 0.0205(8) 0.0104(6) 0.0265(8) 0.0005(6) 0.0013(6) 0.0000(6) C8 0.0221(8) 0.0180(7) 0.0204(7) 0.0027(6) 0.0044(6) -0.0069(6) N5 0.0203(7) 0.0206(6) 0.0201(6) -0.0001(5) 0.0071(5) -0.0079(5) O6 0.0235(6) 0.0317(7) 0.0504(8) 0.0054(6) 0.0216(6) -0.0048(5) N4 0.0146(6) 0.0198(6) 0.0205(6) -0.0038(5) 0.0062(5) -0.0010(5) O4 0.0235(6) 0.0204(6) 0.0373(7) -0.0049(5) 0.0113(5) 0.0039(5) C18 0.0121(7) 0.0174(7) 0.0163(7) -0.0005(5) 0.0039(5) -0.0007(5) C16 0.0154(7) 0.0124(6) 0.0143(6) 0.0004(5) 0.0028(5) -0.0016(5) O1 0.0272(7) 0.0219(6) 0.0369(7) -0.0059(5) 0.0124(5) 0.0061(5) N3 0.0186(6) 0.0142(6) 0.0268(7) -0.0021(5) 0.0039(5) -0.0003(5) C15 0.0110(7) 0.0153(7) 0.0144(6) -0.0008(5) 0.0028(5) -0.0015(5) O5 0.0399(7) 0.0170(6) 0.0354(7) 0.0011(5) 0.0200(6) -0.0076(5) C14 0.0126(7) 0.0134(7) 0.0145(6) 0.0011(5) 0.0025(5) -0.0034(5) C17 0.0138(7) 0.0154(7) 0.0145(6) 0.0007(5) 0.0032(5) -0.0051(5) O3 0.0215(6) 0.0291(6) 0.0403(7) 0.0027(5) 0.0185(5) -0.0036(5) C13 0.0156(7) 0.0113(6) 0.0170(7) -0.0004(5) 0.0026(5) -0.0006(5) O2 0.0293(7) 0.0152(6) 0.0638(9) 0.0104(6) 0.0188(7) -0.0004(5) _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 C1 1.3343(19) . ? N1 C12 1.3655(18) . ? N2 C10 1.330(2) . ? N2 C11 1.3663(18) . ? C11 C7 1.4240(19) . ? C11 C12 1.4593(19) . ? C4 C3 1.415(2) . ? C4 C12 1.4202(19) . ? C4 C5 1.444(2) . ? C1 C2 1.410(2) . ? C7 C8 1.416(2) . ? C7 C6 1.437(2) . ? C2 C3 1.379(2) . ? C9 C8 1.372(2) . ? C9 C10 1.412(2) . ? C5 C6 1.360(2) . ? N5 O5 1.2267(19) . ? N5 O6 1.2297(19) . ? N5 C17 1.4785(18) . ? N4 O3 1.2253(18) . ? N4 O4 1.2341(18) . ? N4 C15 1.4781(18) . ? C18 C13 1.387(2) . ? C18 C17 1.390(2) . ? C16 C17 1.387(2) . ? C16 C15 1.3887(19) . ? O1 N3 1.2276(18) . ? N3 O2 1.2230(19) . ? N3 C13 1.4801(19) . ? C15 C14 1.394(2) . ? C14 C13 1.388(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 C1 N1 C12 117.52(12) . . ? C10 N2 C11 117.14(13) . . ? N2 C11 C7 122.59(13) . . ? N2 C11 C12 118.57(12) . . ? C7 C11 C12 118.82(13) . . ? C3 C4 C12 117.86(13) . . ? C3 C4 C5 121.82(13) . . ? C12 C4 C5 120.31(13) . . ? N1 C1 C2 124.28(14) . . ? N1 C12 C4 122.50(13) . . ? N1 C12 C11 118.62(12) . . ? C4 C12 C11 118.87(12) . . ? C8 C7 C11 117.98(14) . . ? C8 C7 C6 121.50(14) . . ? C11 C7 C6 120.52(13) . . ? C3 C2 C1 118.29(13) . . ? C2 C3 C4 119.55(13) . . ? C8 C9 C10 118.80(14) . . ? N2 C10 C9 124.38(15) . . ? C6 C5 C4 120.81(14) . . ? C5 C6 C7 120.62(14) . . ? C9 C8 C7 119.07(14) . . ? O5 N5 O6 124.71(13) . . ? O5 N5 C17 118.01(13) . . ? O6 N5 C17 117.28(13) . . ? O3 N4 O4 125.07(13) . . ? O3 N4 C15 117.61(13) . . ? O4 N4 C15 117.32(12) . . ? C13 C18 C17 117.01(13) . . ? C17 C16 C15 116.56(13) . . ? O2 N3 O1 124.87(14) . . ? O2 N3 C13 117.70(13) . . ? O1 N3 C13 117.43(13) . . ? C16 C15 C14 123.51(13) . . ? C16 C15 N4 118.19(13) . . ? C14 C15 N4 118.30(12) . . ? C13 C14 C15 116.44(13) . . ? C16 C17 C18 123.23(13) . . ? C16 C17 N5 118.57(13) . . ? C18 C17 N5 118.20(13) . . ? C18 C13 C14 123.23(13) . . ? C18 C13 N3 117.98(13) . . ? C14 C13 N3 118.79(13) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.69 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.361 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.076 ****************************************************** data_TNBPHEN _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2:3 Complex of TNB and Phenazene ; _chemical_name_common '2:3 Complex of TNB and Phenazene' _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 N6 O6' _chemical_formula_sum 'C24 H15 N6 O6' _chemical_formula_weight 483.42 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0781(14) _cell_length_b 9.7139(19) _cell_length_c 15.787(3) _cell_angle_alpha 86.83(3) _cell_angle_beta 88.33(3) _cell_angle_gamma 83.08(3) _cell_volume 1075.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 18.1 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 0.111 _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 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius FAST area detector' _diffrn_measurement_method 'box integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4897 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4897 _reflns_number_gt 3374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MADNES-Messerschmidt & Pflugrath' _computing_cell_refinement 'MADNES-Messerschmidt & Pflugrath' _computing_data_reduction 'MADNES-Messerschmidt & Pflugrath' _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^)+(0.0864P)^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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4897 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8734(3) 1.16889(19) 0.39056(13) 0.0280(4) Uani 1 1 d . . . H1 H 0.9506 1.2032 0.3477 0.034 Uiso 1 1 calc R . . C2 C 0.7235(3) 1.10379(18) 0.36993(11) 0.0224(4) Uani 1 1 d . . . H2B H 0.6978 1.0943 0.3133 0.027 Uiso 1 1 calc R . . C3 C 0.6049(2) 1.04980(16) 0.43532(10) 0.0173(4) Uani 1 1 d . . . C4 C 0.3499(2) 0.93705(16) 0.47779(10) 0.0172(4) Uani 1 1 d . . . C5 C 0.1923(3) 0.86564(18) 0.45889(12) 0.0236(4) Uani 1 1 d . . . H5A H 0.1630 0.8543 0.4028 0.028 Uiso 1 1 calc R . . C6 C 0.0856(3) 0.81442(18) 0.52356(13) 0.0273(4) Uani 1 1 d . . . H6 H -0.0164 0.7675 0.5112 0.033 Uiso 1 1 calc R . . N1 N 0.4551(2) 0.98783(14) 0.41367(9) 0.0186(3) Uani 1 1 d . . . C7 C 0.2915(3) 0.35590(19) 0.35553(11) 0.0222(4) Uani 1 1 d . . . H7A H 0.3383 0.3169 0.4070 0.027 Uiso 1 1 calc R . . C8 C 0.2207(2) 0.49272(18) 0.34936(11) 0.0207(4) Uani 1 1 d . . . H8A H 0.2178 0.5461 0.3966 0.025 Uiso 1 1 calc R . . C9 C 0.1511(2) 0.55407(17) 0.27039(10) 0.0173(4) Uani 1 1 d . . . C10 C 0.0195(2) 0.74235(17) 0.18867(10) 0.0168(4) Uani 1 1 d . . . C11 C -0.0545(3) 0.88568(18) 0.17804(12) 0.0225(4) Uani 1 1 d . . . H11A H -0.0531 0.9433 0.2231 0.027 Uiso 1 1 calc R . . C12 C -0.1264(3) 0.93820(18) 0.10288(12) 0.0246(4) Uani 1 1 d . . . H12A H -0.1741 1.0316 0.0969 0.030 Uiso 1 1 calc R . . C13 C -0.1302(3) 0.85224(19) 0.03264(12) 0.0239(4) Uani 1 1 d . . . H13A H -0.1821 0.8900 -0.0182 0.029 Uiso 1 1 calc R . . C14 C -0.0586(3) 0.71537(18) 0.03913(11) 0.0219(4) Uani 1 1 d . . . H14A H -0.0604 0.6607 -0.0073 0.026 Uiso 1 1 calc R . . C15 C 0.0193(2) 0.65585(17) 0.11725(10) 0.0171(4) Uani 1 1 d . . . C16 C 0.1532(2) 0.46886(17) 0.19862(10) 0.0162(3) Uani 1 1 d . . . C17 C 0.2275(2) 0.32562(17) 0.20820(11) 0.0198(4) Uani 1 1 d . . . H17A H 0.2296 0.2693 0.1624 0.024 Uiso 1 1 calc R . . C18 C 0.2949(3) 0.27159(18) 0.28417(11) 0.0215(4) Uani 1 1 d . . . H18A H 0.3440 0.1784 0.2897 0.026 Uiso 1 1 calc R . . N2 N 0.0845(2) 0.69084(14) 0.26470(9) 0.0187(3) Uani 1 1 d . . . N3 N 0.0859(2) 0.52050(14) 0.12306(9) 0.0182(3) Uani 1 1 d . . . C19 C 0.6415(2) 0.61877(17) 0.30622(10) 0.0170(4) Uani 1 1 d . . . C20 C 0.5607(2) 0.74412(17) 0.26865(10) 0.0164(3) Uani 1 1 d . . . H20A H 0.5385 0.8244 0.2987 0.020 Uiso 1 1 calc R . . C21 C 0.5151(2) 0.74292(16) 0.18424(10) 0.0164(3) Uani 1 1 d . . . C22 C 0.5472(2) 0.62578(17) 0.13692(10) 0.0173(4) Uani 1 1 d . . . H22A H 0.5149 0.6281 0.0801 0.021 Uiso 1 1 calc R . . C23 C 0.6304(2) 0.50464(16) 0.17888(10) 0.0172(4) Uani 1 1 d . . . C24 C 0.6769(2) 0.49761(17) 0.26317(10) 0.0177(4) Uani 1 1 d . . . H24A H 0.7298 0.4149 0.2901 0.021 Uiso 1 1 calc R . . N4 N 0.6923(2) 0.61304(15) 0.39622(9) 0.0243(4) Uani 1 1 d . . . N5 N 0.4281(2) 0.87367(15) 0.14151(9) 0.0210(3) Uani 1 1 d . . . N6 N 0.6716(2) 0.37783(15) 0.13078(9) 0.0231(3) Uani 1 1 d . . . O1 O 0.7331(3) 0.49944(15) 0.43149(9) 0.0532(5) Uani 1 1 d . . . O2 O 0.6924(2) 0.72288(14) 0.42998(8) 0.0378(4) Uani 1 1 d . . . O3 O 0.4051(2) 0.97751(13) 0.18332(9) 0.0320(3) Uani 1 1 d . . . O4 O 0.3844(2) 0.87009(13) 0.06746(8) 0.0302(3) Uani 1 1 d . . . O5 O 0.6216(2) 0.38338(15) 0.05765(9) 0.0430(4) Uani 1 1 d . . . O6 O 0.7553(2) 0.27474(13) 0.16770(8) 0.0310(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0234(11) 0.0224(9) 0.0360(11) 0.0081(8) 0.0050(8) 0.0005(8) C2 0.0239(10) 0.0220(9) 0.0194(8) 0.0030(7) 0.0029(7) 0.0030(7) C3 0.0199(9) 0.0127(7) 0.0180(8) -0.0003(6) -0.0013(7) 0.0035(7) C4 0.0189(9) 0.0124(7) 0.0191(8) -0.0018(6) -0.0017(7) 0.0029(7) C5 0.0233(10) 0.0181(8) 0.0292(9) -0.0037(7) -0.0073(8) 0.0018(7) C6 0.0192(10) 0.0192(9) 0.0436(11) 0.0015(8) -0.0036(8) -0.0029(7) N1 0.0231(8) 0.0137(7) 0.0182(7) -0.0019(5) -0.0015(6) 0.0016(6) C7 0.0201(10) 0.0283(9) 0.0176(8) 0.0060(7) -0.0020(7) -0.0033(8) C8 0.0187(10) 0.0278(9) 0.0162(8) -0.0029(7) -0.0002(7) -0.0043(7) C9 0.0138(9) 0.0203(8) 0.0181(8) -0.0008(6) 0.0013(7) -0.0034(7) C10 0.0129(9) 0.0183(8) 0.0191(8) -0.0013(6) 0.0037(7) -0.0019(7) C11 0.0206(10) 0.0180(8) 0.0286(9) -0.0031(7) 0.0041(7) -0.0015(7) C12 0.0233(10) 0.0149(8) 0.0343(10) 0.0033(7) 0.0063(8) -0.0001(7) C13 0.0215(10) 0.0240(9) 0.0241(9) 0.0074(7) 0.0008(8) 0.0007(7) C14 0.0241(10) 0.0227(9) 0.0183(8) 0.0000(7) 0.0006(7) -0.0016(7) C15 0.0159(9) 0.0177(8) 0.0176(8) -0.0008(6) 0.0021(7) -0.0017(7) C16 0.0149(9) 0.0175(8) 0.0164(8) 0.0000(6) 0.0011(6) -0.0032(7) C17 0.0196(9) 0.0183(8) 0.0213(8) -0.0017(6) -0.0008(7) -0.0008(7) C18 0.0189(9) 0.0187(8) 0.0258(9) 0.0028(7) 0.0005(7) 0.0005(7) N2 0.0164(8) 0.0201(7) 0.0198(7) -0.0023(6) 0.0025(6) -0.0023(6) N3 0.0184(8) 0.0180(7) 0.0178(7) -0.0003(5) -0.0003(6) -0.0007(6) C19 0.0182(9) 0.0201(8) 0.0127(8) -0.0010(6) -0.0006(6) -0.0022(7) C20 0.0161(9) 0.0155(8) 0.0178(8) -0.0027(6) -0.0011(7) -0.0019(6) C21 0.0153(9) 0.0162(8) 0.0175(8) 0.0010(6) -0.0001(7) -0.0017(7) C22 0.0182(9) 0.0201(8) 0.0135(8) -0.0008(6) -0.0016(7) -0.0013(7) C23 0.0190(9) 0.0161(8) 0.0167(8) -0.0042(6) 0.0014(7) -0.0021(7) C24 0.0188(9) 0.0164(8) 0.0175(8) 0.0013(6) -0.0009(7) -0.0008(7) N4 0.0315(9) 0.0227(8) 0.0170(7) -0.0021(6) -0.0058(6) 0.0051(7) N5 0.0215(8) 0.0184(7) 0.0220(8) 0.0012(6) -0.0021(6) 0.0012(6) N6 0.0286(9) 0.0196(7) 0.0208(7) -0.0049(6) -0.0017(6) 0.0011(6) O1 0.1072(15) 0.0256(8) 0.0232(7) 0.0018(6) -0.0236(8) 0.0103(8) O2 0.0572(10) 0.0284(7) 0.0261(7) -0.0107(6) -0.0177(7) 0.0098(7) O3 0.0467(9) 0.0164(6) 0.0311(7) -0.0040(5) -0.0061(6) 0.0055(6) O4 0.0395(9) 0.0276(7) 0.0215(7) 0.0036(5) -0.0109(6) 0.0049(6) O5 0.0670(11) 0.0354(8) 0.0241(7) -0.0142(6) -0.0170(7) 0.0133(7) O6 0.0441(9) 0.0173(6) 0.0297(7) -0.0039(5) -0.0032(6) 0.0061(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 C1 C2 1.355(3) . ? C1 C6 1.417(3) 2_676 ? C2 C3 1.429(2) . ? C3 N1 1.342(2) . ? C3 C4 1.434(2) 2_676 ? C4 N1 1.346(2) . ? C4 C5 1.429(3) . ? C4 C3 1.434(2) 2_676 ? C5 C6 1.360(3) . ? C6 C1 1.417(3) 2_676 ? C7 C8 1.362(2) . ? C7 C18 1.427(2) . ? C8 C9 1.427(2) . ? C9 N2 1.354(2) . ? C9 C16 1.438(2) . ? C10 N2 1.346(2) . ? C10 C11 1.430(2) . ? C10 C15 1.443(2) . ? C11 C12 1.354(3) . ? C12 C13 1.427(3) . ? C13 C14 1.364(2) . ? C14 C15 1.429(2) . ? C15 N3 1.341(2) . ? C16 N3 1.346(2) . ? C16 C17 1.428(2) . ? C17 C18 1.358(2) . ? C19 C24 1.385(2) . ? C19 C20 1.391(2) . ? C19 N4 1.472(2) . ? C20 C21 1.381(2) . ? C21 C22 1.388(2) . ? C21 N5 1.479(2) . ? C22 C23 1.393(2) . ? C23 C24 1.376(2) . ? C23 N6 1.477(2) . ? N4 O1 1.215(2) . ? N4 O2 1.219(2) . ? N5 O4 1.2212(19) . ? N5 O3 1.2278(19) . ? N6 O5 1.2138(19) . ? N6 O6 1.2273(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 C2 C1 C6 121.03(18) . 2_676 ? C1 C2 C3 119.96(17) . . ? N1 C3 C2 119.11(15) . . ? N1 C3 C4 121.97(16) . 2_676 ? C2 C3 C4 118.92(16) . 2_676 ? N1 C4 C5 119.33(15) . . ? N1 C4 C3 121.40(16) . 2_676 ? C5 C4 C3 119.26(16) . 2_676 ? C6 C5 C4 119.43(17) . . ? C5 C6 C1 121.36(18) . 2_676 ? C3 N1 C4 116.63(14) . . ? C8 C7 C18 120.95(16) . . ? C7 C8 C9 119.96(16) . . ? N2 C9 C8 119.37(15) . . ? N2 C9 C16 121.55(15) . . ? C8 C9 C16 119.08(15) . . ? N2 C10 C11 119.69(15) . . ? N2 C10 C15 121.66(15) . . ? C11 C10 C15 118.64(15) . . ? C12 C11 C10 120.51(17) . . ? C11 C12 C13 120.94(16) . . ? C14 C13 C12 120.80(17) . . ? C13 C14 C15 120.06(16) . . ? N3 C15 C14 119.32(15) . . ? N3 C15 C10 121.64(15) . . ? C14 C15 C10 119.02(15) . . ? N3 C16 C17 119.33(15) . . ? N3 C16 C9 121.66(15) . . ? C17 C16 C9 119.01(15) . . ? C18 C17 C16 120.10(16) . . ? C17 C18 C7 120.89(16) . . ? C10 N2 C9 116.53(14) . . ? C15 N3 C16 116.95(14) . . ? C24 C19 C20 123.24(15) . . ? C24 C19 N4 117.78(14) . . ? C20 C19 N4 118.98(14) . . ? C21 C20 C19 116.36(15) . . ? C20 C21 C22 123.64(15) . . ? C20 C21 N5 118.39(14) . . ? C22 C21 N5 117.97(14) . . ? C21 C22 C23 116.54(15) . . ? C24 C23 C22 123.01(15) . . ? C24 C23 N6 118.34(15) . . ? C22 C23 N6 118.65(14) . . ? C23 C24 C19 117.20(15) . . ? O1 N4 O2 124.50(15) . . ? O1 N4 C19 117.87(15) . . ? O2 N4 C19 117.63(14) . . ? O4 N5 O3 125.01(15) . . ? O4 N5 C21 117.58(14) . . ? O3 N5 C21 117.41(14) . . ? O5 N6 O6 124.80(15) . . ? O5 N6 C23 117.78(14) . . ? O6 N6 C23 117.42(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.261 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.066