Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Golding, Bernard Thomas' 'Bleasdale, C.' 'Cleg, William' 'Henderson, Alistair P.' 'Henderson, R.' 'Leclercq, Amelie' 'Mutlu, Ersa' _publ_contact_author_name 'Prof Bernard Thomas Golding' _publ_contact_author_address ; Department of Chemistry Newcastle University Bedson Building Newcastle upon Tyne Tyne & Wear NE1 7RU UNITED KINGDOM ; _publ_contact_author_email 'B.T.GOLDING@NCL.AC.UK' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Trapping of Benzene Oxide-Oxepin and Methyl-substituted Derivatives with 4-Phenyl- and 4-Pentafluorophenyl-1,2,4-triazoline-3,5-dione ; data_btg45 _database_code_CSD 188253 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N3 O3' _chemical_formula_weight 269.26 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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.8897(7) _cell_length_b 14.2214(9) _cell_length_c 15.2607(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2363.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 18837 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17468 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 28.59 _reflns_number_total 2845 _reflns_number_gt 2399 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0542P)^2^+1.0063P] 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 2845 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 C1 C 0.01483(13) 0.36433(9) 0.42577(8) 0.0248(3) Uani 1 1 d . . . H1 H 0.0086 0.4044 0.3737 0.030 Uiso 1 1 calc R . . C2 C 0.14131(13) 0.36634(10) 0.46495(9) 0.0293(3) Uani 1 1 d . . . H2 H 0.2049 0.4024 0.4421 0.035 Uiso 1 1 calc R . . C3 C 0.15420(13) 0.31193(10) 0.53516(9) 0.0286(3) Uani 1 1 d . . . H3 H 0.2276 0.3065 0.5659 0.034 Uiso 1 1 calc R . . C4 C 0.03933(13) 0.26017(9) 0.56011(8) 0.0234(3) Uani 1 1 d . . . H4 H 0.0514 0.2206 0.6120 0.028 Uiso 1 1 calc R . . C5 C -0.06774(13) 0.32903(9) 0.57184(9) 0.0264(3) Uani 1 1 d . . . H5 H -0.1418 0.3072 0.6022 0.032 Uiso 1 1 calc R . . C6 C -0.08185(13) 0.38933(9) 0.49487(9) 0.0263(3) Uani 1 1 d . . . H6 H -0.1647 0.4063 0.4755 0.032 Uiso 1 1 calc R . . O1 O -0.03666(10) 0.42691(7) 0.57622(6) 0.0308(2) Uani 1 1 d . . . N1 N 0.00071(10) 0.20386(7) 0.48173(6) 0.0203(2) Uani 1 1 d . . . N2 N -0.01551(10) 0.26304(7) 0.40569(7) 0.0221(2) Uani 1 1 d . . . C7 C 0.07277(11) 0.12755(8) 0.45777(8) 0.0192(2) Uani 1 1 d . . . C8 C 0.04302(12) 0.21932(9) 0.33580(8) 0.0233(3) Uani 1 1 d . . . O2 O 0.05074(11) 0.24933(7) 0.26183(6) 0.0348(3) Uani 1 1 d . . . O3 O 0.11307(9) 0.06773(6) 0.50613(6) 0.0245(2) Uani 1 1 d . . . N3 N 0.08596(10) 0.13306(7) 0.36678(6) 0.0207(2) Uani 1 1 d . . . C9 C 0.14416(11) 0.06316(9) 0.31341(8) 0.0202(2) Uani 1 1 d . . . C10 C 0.11377(12) -0.03055(9) 0.32584(9) 0.0241(3) Uani 1 1 d . . . H10 H 0.0561 -0.0479 0.3678 0.029 Uiso 1 1 calc R . . C11 C 0.17134(14) -0.09811(10) 0.27434(9) 0.0298(3) Uani 1 1 d . . . H11 H 0.1533 -0.1614 0.2827 0.036 Uiso 1 1 calc R . . C12 C 0.25521(14) -0.07195(11) 0.21087(9) 0.0323(3) Uani 1 1 d . . . H12 H 0.2929 -0.1176 0.1765 0.039 Uiso 1 1 calc R . . C13 C 0.28312(14) 0.02185(11) 0.19843(9) 0.0323(3) Uani 1 1 d . . . H13 H 0.3387 0.0392 0.1551 0.039 Uiso 1 1 calc R . . C14 C 0.22861(13) 0.09026(10) 0.25021(8) 0.0273(3) Uani 1 1 d . . . H14 H 0.2484 0.1534 0.2427 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 C1 0.0361(7) 0.0195(6) 0.0186(6) -0.0010(5) 0.0029(5) 0.0013(5) C2 0.0292(7) 0.0281(6) 0.0305(7) -0.0076(5) 0.0086(6) -0.0045(5) C3 0.0254(6) 0.0330(7) 0.0276(7) -0.0111(5) -0.0032(5) 0.0017(5) C4 0.0304(7) 0.0261(6) 0.0138(5) -0.0032(4) 0.0001(5) 0.0036(5) C5 0.0304(7) 0.0259(6) 0.0230(6) -0.0025(5) 0.0067(5) 0.0030(5) C6 0.0296(7) 0.0240(6) 0.0252(6) -0.0035(5) 0.0011(5) 0.0039(5) O1 0.0433(6) 0.0257(5) 0.0234(5) -0.0062(4) 0.0042(4) 0.0034(4) N1 0.0252(5) 0.0211(5) 0.0145(5) 0.0010(4) 0.0000(4) 0.0015(4) N2 0.0306(6) 0.0211(5) 0.0146(5) 0.0011(4) -0.0020(4) 0.0032(4) C7 0.0189(6) 0.0228(6) 0.0158(5) -0.0008(4) -0.0001(4) -0.0021(4) C8 0.0305(7) 0.0228(6) 0.0167(6) -0.0011(4) -0.0025(5) 0.0019(5) O2 0.0606(7) 0.0289(5) 0.0150(4) 0.0020(4) 0.0012(4) 0.0092(5) O3 0.0296(5) 0.0255(5) 0.0184(4) 0.0032(3) -0.0009(4) 0.0031(4) N3 0.0266(5) 0.0206(5) 0.0148(5) -0.0004(4) 0.0003(4) 0.0021(4) C9 0.0212(6) 0.0241(6) 0.0154(5) -0.0031(4) -0.0023(4) 0.0022(5) C10 0.0257(6) 0.0248(6) 0.0217(6) 0.0001(5) -0.0001(5) 0.0017(5) C11 0.0374(8) 0.0235(6) 0.0285(7) -0.0031(5) -0.0037(6) 0.0054(6) C12 0.0348(7) 0.0371(7) 0.0251(6) -0.0078(6) -0.0005(6) 0.0137(6) C13 0.0291(7) 0.0438(8) 0.0241(7) -0.0026(6) 0.0066(5) 0.0037(6) C14 0.0292(7) 0.0295(6) 0.0233(6) -0.0013(5) 0.0036(5) -0.0026(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 C1 C2 1.502(2) . ? C1 N2 1.5093(16) . ? C1 C6 1.5320(18) . ? C2 C3 1.329(2) . ? C3 C4 1.501(2) . ? C4 N1 1.4997(16) . ? C4 C5 1.5331(18) . ? C5 O1 1.4341(17) . ? C5 C6 1.4625(19) . ? C6 O1 1.4383(16) . ? N1 C7 1.3882(16) . ? N1 N2 1.4444(14) . ? N2 C8 1.3894(16) . ? C7 O3 1.2087(15) . ? C7 N3 1.3981(15) . ? C8 O2 1.2098(15) . ? C8 N3 1.3954(16) . ? N3 C9 1.4329(15) . ? C9 C10 1.3862(18) . ? C9 C14 1.3872(18) . ? C10 C11 1.3906(18) . ? C11 C12 1.382(2) . ? C12 C13 1.381(2) . ? C13 C14 1.3868(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 N2 107.44(11) . . ? C2 C1 C6 110.59(11) . . ? N2 C1 C6 102.17(10) . . ? C3 C2 C1 114.00(12) . . ? C2 C3 C4 113.71(12) . . ? N1 C4 C3 107.06(10) . . ? N1 C4 C5 102.76(10) . . ? C3 C4 C5 110.51(11) . . ? O1 C5 C6 59.54(8) . . ? O1 C5 C4 116.48(12) . . ? C6 C5 C4 111.14(11) . . ? O1 C6 C5 59.25(8) . . ? O1 C6 C1 116.44(12) . . ? C5 C6 C1 110.16(11) . . ? C5 O1 C6 61.21(9) . . ? C7 N1 N2 108.24(9) . . ? C7 N1 C4 117.97(10) . . ? N2 N1 C4 111.34(10) . . ? C8 N2 N1 107.45(10) . . ? C8 N2 C1 118.85(11) . . ? N1 N2 C1 111.49(9) . . ? O3 C7 N1 126.49(11) . . ? O3 C7 N3 127.48(11) . . ? N1 C7 N3 106.01(10) . . ? O2 C8 N2 126.18(12) . . ? O2 C8 N3 127.09(12) . . ? N2 C8 N3 106.68(10) . . ? C8 N3 C7 110.57(10) . . ? C8 N3 C9 124.43(10) . . ? C7 N3 C9 124.83(10) . . ? C10 C9 C14 121.36(12) . . ? C10 C9 N3 118.91(11) . . ? C14 C9 N3 119.72(11) . . ? C9 C10 C11 118.64(12) . . ? C12 C11 C10 120.52(13) . . ? C13 C12 C11 120.11(13) . . ? C12 C13 C14 120.33(13) . . ? C13 C14 C9 119.02(13) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.314 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.046 data_btg50 _database_code_CSD 188254 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N3 O3' _chemical_formula_weight 297.31 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 orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 13.5339(10) _cell_length_b 11.3119(8) _cell_length_c 9.3316(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1428.61(18) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 6119 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.098 _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 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7985 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1767 _reflns_number_gt 1606 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0511P)^2^+0.3105P] 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 SHELXL _refine_ls_extinction_coef 0.0034(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(15) _refine_ls_number_reflns 1767 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 C1 C 0.86832(17) 0.5150(2) 0.5529(2) 0.0218(5) Uani 1 1 d . . . H1 H 0.8544 0.4289 0.5389 0.026 Uiso 1 1 calc R . . C2 C 0.97944(18) 0.5440(2) 0.5354(3) 0.0237(5) Uani 1 1 d . . . C3 C 0.99644(17) 0.6705(2) 0.5560(3) 0.0255(5) Uani 1 1 d . . . C4 C 0.89789(18) 0.7350(2) 0.5868(3) 0.0239(5) Uani 1 1 d . . . H4 H 0.9073 0.8222 0.5980 0.029 Uiso 1 1 calc R . . C5 C 0.80667(18) 0.5912(2) 0.4561(3) 0.0262(5) Uani 1 1 d . . . H5 H 0.7610 0.5602 0.3886 0.031 Uiso 1 1 calc R . . C6 C 0.82207(18) 0.7058(2) 0.4739(3) 0.0262(5) Uani 1 1 d . . . H6 H 0.7883 0.7646 0.4202 0.031 Uiso 1 1 calc R . . C7 C 1.0511(2) 0.4469(3) 0.5711(3) 0.0369(7) Uani 1 1 d . . . H7A H 1.1188 0.4772 0.5645 0.055 Uiso 1 1 calc R . . H7B H 1.0426 0.3815 0.5034 0.055 Uiso 1 1 calc R . . H7C H 1.0386 0.4187 0.6688 0.055 Uiso 1 1 calc R . . C8 C 1.0871(2) 0.7231(3) 0.6207(4) 0.0420(8) Uani 1 1 d . . . H8A H 1.0990 0.8013 0.5788 0.063 Uiso 1 1 calc R . . H8B H 1.1438 0.6717 0.6013 0.063 Uiso 1 1 calc R . . H8C H 1.0780 0.7309 0.7244 0.063 Uiso 1 1 calc R . . C9 C 0.76355(17) 0.5244(2) 0.7764(3) 0.0207(5) Uani 1 1 d . . . C10 C 0.79400(16) 0.7231(2) 0.8116(3) 0.0201(5) Uani 1 1 d . . . C11 C 0.66205(16) 0.6304(2) 0.9624(3) 0.0209(5) Uani 1 1 d . . . C12 C 0.56924(18) 0.5838(2) 0.9348(3) 0.0267(5) Uani 1 1 d . . . H12 H 0.5558 0.5464 0.8458 0.032 Uiso 1 1 calc R . . C13 C 0.4959(2) 0.5925(3) 1.0392(4) 0.0343(7) Uani 1 1 d . . . H13 H 0.4323 0.5598 1.0218 0.041 Uiso 1 1 calc R . . C14 C 0.5154(2) 0.6486(2) 1.1682(3) 0.0330(6) Uani 1 1 d . . . H14 H 0.4650 0.6553 1.2386 0.040 Uiso 1 1 calc R . . C15 C 0.6083(2) 0.6951(3) 1.1943(3) 0.0319(6) Uani 1 1 d . . . H15 H 0.6214 0.7337 1.2827 0.038 Uiso 1 1 calc R . . C16 C 0.68234(19) 0.6854(2) 1.0923(3) 0.0255(5) Uani 1 1 d . . . H16 H 0.7464 0.7161 1.1110 0.031 Uiso 1 1 calc R . . N1 N 0.84839(14) 0.55401(17) 0.7031(2) 0.0204(4) Uani 1 1 d . . . N2 N 0.86681(14) 0.67763(17) 0.7238(2) 0.0207(4) Uani 1 1 d . . . N3 N 0.73793(14) 0.62549(16) 0.8551(2) 0.0196(4) Uani 1 1 d . . . O1 O 1.00433(13) 0.61893(16) 0.4152(2) 0.0278(4) Uani 1 1 d . . . O2 O 0.72234(13) 0.42943(15) 0.7768(2) 0.0299(4) Uani 1 1 d . . . O3 O 0.78268(13) 0.82525(15) 0.8458(2) 0.0276(4) 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 0.0239(11) 0.0212(11) 0.0204(12) -0.0022(9) 0.0051(9) 0.0014(9) C2 0.0248(11) 0.0306(13) 0.0158(11) 0.0025(10) 0.0059(9) 0.0044(10) C3 0.0205(11) 0.0357(14) 0.0204(12) 0.0005(11) 0.0052(10) -0.0038(10) C4 0.0251(12) 0.0209(11) 0.0256(12) 0.0035(10) 0.0079(10) -0.0026(10) C5 0.0227(11) 0.0349(14) 0.0211(12) 0.0015(11) 0.0001(10) -0.0029(10) C6 0.0241(12) 0.0290(13) 0.0255(13) 0.0092(11) 0.0044(10) 0.0064(10) C7 0.0374(15) 0.0436(16) 0.0296(14) 0.0079(13) 0.0113(12) 0.0169(13) C8 0.0252(14) 0.059(2) 0.0416(17) -0.0131(15) 0.0058(12) -0.0133(14) C9 0.0227(11) 0.0212(11) 0.0181(10) 0.0048(9) 0.0031(9) 0.0044(9) C10 0.0166(10) 0.0248(12) 0.0188(11) 0.0015(9) -0.0014(8) -0.0014(9) C11 0.0212(10) 0.0202(11) 0.0214(11) 0.0025(10) 0.0048(9) 0.0023(9) C12 0.0268(12) 0.0272(12) 0.0262(13) -0.0007(11) 0.0025(11) -0.0042(10) C13 0.0230(12) 0.0314(14) 0.0486(18) 0.0067(13) 0.0083(12) -0.0038(11) C14 0.0324(13) 0.0322(13) 0.0345(15) 0.0051(12) 0.0183(11) 0.0051(11) C15 0.0403(15) 0.0335(13) 0.0220(12) -0.0005(11) 0.0085(11) 0.0074(12) C16 0.0241(12) 0.0294(13) 0.0230(12) 0.0002(10) 0.0009(10) 0.0022(10) N1 0.0224(9) 0.0183(9) 0.0204(9) 0.0028(8) 0.0042(8) 0.0023(8) N2 0.0217(9) 0.0186(9) 0.0219(10) 0.0010(8) 0.0027(8) -0.0008(8) N3 0.0184(9) 0.0207(10) 0.0198(9) 0.0023(8) 0.0024(8) 0.0009(7) O1 0.0315(10) 0.0306(9) 0.0214(9) 0.0018(7) 0.0078(7) -0.0025(7) O2 0.0353(10) 0.0197(8) 0.0348(10) 0.0017(8) 0.0127(8) -0.0044(7) O3 0.0301(9) 0.0210(9) 0.0318(10) -0.0047(8) 0.0063(8) -0.0033(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 C1 N1 1.494(3) . ? C1 C5 1.502(3) . ? C1 C2 1.548(3) . ? C2 O1 1.446(3) . ? C2 C3 1.462(4) . ? C2 C7 1.503(4) . ? C3 O1 1.441(3) . ? C3 C8 1.491(4) . ? C3 C4 1.547(3) . ? C4 N2 1.494(3) . ? C4 C6 1.507(4) . ? C5 C6 1.323(4) . ? C9 O2 1.211(3) . ? C9 N1 1.378(3) . ? C9 N3 1.403(3) . ? C10 O3 1.209(3) . ? C10 N2 1.381(3) . ? C10 N3 1.400(3) . ? C11 C12 1.386(3) . ? C11 C16 1.390(4) . ? C11 N3 1.435(3) . ? C12 C13 1.394(4) . ? C13 C14 1.386(5) . ? C14 C15 1.384(4) . ? C15 C16 1.387(4) . ? N1 N2 1.434(3) . ? 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 N1 C1 C5 107.09(18) . . ? N1 C1 C2 102.20(19) . . ? C5 C1 C2 110.76(19) . . ? O1 C2 C3 59.42(15) . . ? O1 C2 C7 116.8(2) . . ? C3 C2 C7 125.8(2) . . ? O1 C2 C1 115.62(19) . . ? C3 C2 C1 110.3(2) . . ? C7 C2 C1 116.6(2) . . ? O1 C3 C2 59.72(15) . . ? O1 C3 C8 118.0(2) . . ? C2 C3 C8 125.0(2) . . ? O1 C3 C4 115.1(2) . . ? C2 C3 C4 110.5(2) . . ? C8 C3 C4 116.5(2) . . ? N2 C4 C6 108.16(19) . . ? N2 C4 C3 101.39(19) . . ? C6 C4 C3 110.7(2) . . ? C6 C5 C1 113.6(2) . . ? C5 C6 C4 114.1(2) . . ? O2 C9 N1 127.0(2) . . ? O2 C9 N3 127.4(2) . . ? N1 C9 N3 105.54(19) . . ? O3 C10 N2 127.1(2) . . ? O3 C10 N3 127.5(2) . . ? N2 C10 N3 105.39(19) . . ? C12 C11 C16 120.7(2) . . ? C12 C11 N3 120.3(2) . . ? C16 C11 N3 119.0(2) . . ? C11 C12 C13 119.3(2) . . ? C14 C13 C12 120.2(2) . . ? C15 C14 C13 120.0(3) . . ? C14 C15 C16 120.3(3) . . ? C15 C16 C11 119.4(2) . . ? C9 N1 N2 108.37(18) . . ? C9 N1 C1 123.0(2) . . ? N2 N1 C1 112.55(18) . . ? C10 N2 N1 108.60(17) . . ? C10 N2 C4 123.18(19) . . ? N1 N2 C4 110.92(18) . . ? C10 N3 C9 110.91(19) . . ? C10 N3 C11 124.02(19) . . ? C9 N3 C11 125.03(19) . . ? C3 O1 C2 60.87(17) . . ? 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 N1 C1 C2 O1 -125.0(2) . . . . ? C5 C1 C2 O1 -11.2(3) . . . . ? N1 C1 C2 C3 -60.1(2) . . . . ? C5 C1 C2 C3 53.7(3) . . . . ? N1 C1 C2 C7 92.0(2) . . . . ? C5 C1 C2 C7 -154.2(2) . . . . ? C7 C2 C3 O1 102.6(3) . . . . ? C1 C2 C3 O1 -108.5(2) . . . . ? O1 C2 C3 C8 -104.8(3) . . . . ? C7 C2 C3 C8 -2.2(4) . . . . ? C1 C2 C3 C8 146.7(3) . . . . ? O1 C2 C3 C4 107.8(2) . . . . ? C7 C2 C3 C4 -149.5(2) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? O1 C3 C4 N2 127.5(2) . . . . ? C2 C3 C4 N2 62.4(2) . . . . ? C8 C3 C4 N2 -88.1(3) . . . . ? O1 C3 C4 C6 12.9(3) . . . . ? C2 C3 C4 C6 -52.2(3) . . . . ? C8 C3 C4 C6 157.3(2) . . . . ? N1 C1 C5 C6 55.5(3) . . . . ? C2 C1 C5 C6 -55.2(3) . . . . ? C1 C5 C6 C4 0.1(3) . . . . ? N2 C4 C6 C5 -55.6(3) . . . . ? C3 C4 C6 C5 54.7(3) . . . . ? C16 C11 C12 C13 0.0(4) . . . . ? N3 C11 C12 C13 -178.2(2) . . . . ? C11 C12 C13 C14 0.9(4) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C11 1.1(4) . . . . ? C12 C11 C16 C15 -0.9(4) . . . . ? N3 C11 C16 C15 177.3(2) . . . . ? O2 C9 N1 N2 175.5(2) . . . . ? N3 C9 N1 N2 -7.2(2) . . . . ? O2 C9 N1 C1 41.3(4) . . . . ? N3 C9 N1 C1 -141.4(2) . . . . ? C5 C1 N1 C9 76.7(3) . . . . ? C2 C1 N1 C9 -166.8(2) . . . . ? C5 C1 N1 N2 -55.9(2) . . . . ? C2 C1 N1 N2 60.6(2) . . . . ? O3 C10 N2 N1 -175.7(2) . . . . ? N3 C10 N2 N1 5.7(2) . . . . ? O3 C10 N2 C4 -43.6(4) . . . . ? N3 C10 N2 C4 137.8(2) . . . . ? C9 N1 N2 C10 0.9(2) . . . . ? C1 N1 N2 C10 140.29(19) . . . . ? C9 N1 N2 C4 -137.4(2) . . . . ? C1 N1 N2 C4 2.0(2) . . . . ? C6 C4 N2 C10 -78.4(3) . . . . ? C3 C4 N2 C10 165.1(2) . . . . ? C6 C4 N2 N1 52.8(2) . . . . ? C3 C4 N2 N1 -63.7(2) . . . . ? O3 C10 N3 C9 170.9(2) . . . . ? N2 C10 N3 C9 -10.5(3) . . . . ? O3 C10 N3 C11 -7.0(4) . . . . ? N2 C10 N3 C11 171.6(2) . . . . ? O2 C9 N3 C10 -171.6(2) . . . . ? N1 C9 N3 C10 11.1(3) . . . . ? O2 C9 N3 C11 6.2(4) . . . . ? N1 C9 N3 C11 -171.0(2) . . . . ? C12 C11 N3 C10 129.5(2) . . . . ? C16 C11 N3 C10 -48.7(3) . . . . ? C12 C11 N3 C9 -48.1(3) . . . . ? C16 C11 N3 C9 133.7(2) . . . . ? C8 C3 O1 C2 116.2(3) . . . . ? C4 C3 O1 C2 -100.0(2) . . . . ? C7 C2 O1 C3 -117.6(3) . . . . ? C1 C2 O1 C3 99.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.247 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.043 data_btg48 _database_code_CSD 188255 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 Cl4 N6 O5' _chemical_formula_weight 642.32 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1142(8) _cell_length_b 9.5955(9) _cell_length_c 17.0216(15) _cell_angle_alpha 85.792(2) _cell_angle_beta 78.365(2) _cell_angle_gamma 74.561(2) _cell_volume 1405.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 7498 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.25 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12071 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.43 _reflns_number_total 6313 _reflns_number_gt 4581 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0688P)^2^+0.8750P] 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 SHELXL _refine_ls_extinction_coef 0.0049(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6313 _refine_ls_number_parameters 392 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.004 _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 C1 C 0.0900(3) 0.4715(3) 0.14149(14) 0.0179(5) Uani 1 1 d . . . H1 H -0.0031 0.5169 0.1171 0.021 Uiso 1 1 calc R . . C2 C 0.1857(3) 0.5798(3) 0.14886(15) 0.0203(5) Uani 1 1 d . . . H2 H 0.2042 0.6345 0.0971 0.024 Uiso 1 1 calc R . . C3 C 0.3358(3) 0.4695(3) 0.16170(14) 0.0186(5) Uani 1 1 d . . . H3 H 0.4260 0.5136 0.1507 0.022 Uiso 1 1 calc R . . C4 C 0.3102(3) 0.4078(3) 0.24832(14) 0.0178(5) Uani 1 1 d . . . C5 C 0.4537(3) 0.2992(3) 0.26727(15) 0.0222(5) Uani 1 1 d . . . H5A H 0.5404 0.3444 0.2581 0.033 Uiso 1 1 calc R . . H5B H 0.4797 0.2157 0.2325 0.033 Uiso 1 1 calc R . . H5C H 0.4337 0.2672 0.3235 0.033 Uiso 1 1 calc R . . C6 C 0.1244(3) 0.6813(3) 0.21696(16) 0.0258(6) Uani 1 1 d . . . H6 H 0.0502 0.7697 0.2101 0.031 Uiso 1 1 calc R . . C7 C 0.1701(3) 0.6523(3) 0.28680(16) 0.0261(6) Uani 1 1 d . . . C8 C 0.1272(4) 0.7485(3) 0.35687(18) 0.0375(7) Uani 1 1 d . . . H8A H 0.0681 0.8446 0.3420 0.056 Uiso 1 1 calc R . . H8B H 0.2215 0.7566 0.3734 0.056 Uiso 1 1 calc R . . H8C H 0.0638 0.7078 0.4014 0.056 Uiso 1 1 calc R . . C9 C 0.2126(3) 0.3368(3) 0.01122(14) 0.0182(5) Uani 1 1 d . . . C10 C 0.4564(3) 0.3374(3) 0.03179(14) 0.0181(5) Uani 1 1 d . . . C11 C 0.4388(3) 0.2488(3) -0.10055(15) 0.0199(5) Uani 1 1 d . . . C12 C 0.3844(3) 0.3179(3) -0.16697(15) 0.0247(5) Uani 1 1 d . . . H12 H 0.3074 0.4074 -0.1618 0.030 Uiso 1 1 calc R . . C13 C 0.4438(3) 0.2545(3) -0.24165(17) 0.0328(6) Uani 1 1 d . . . H13 H 0.4067 0.3005 -0.2878 0.039 Uiso 1 1 calc R . . C14 C 0.5568(3) 0.1247(4) -0.24873(18) 0.0359(7) Uani 1 1 d . . . H14 H 0.5963 0.0812 -0.2997 0.043 Uiso 1 1 calc R . . C15 C 0.6122(3) 0.0585(3) -0.18222(18) 0.0324(6) Uani 1 1 d . . . H15 H 0.6909 -0.0299 -0.1877 0.039 Uiso 1 1 calc R . . C16 C 0.5543(3) 0.1195(3) -0.10727(16) 0.0256(6) Uani 1 1 d . . . H16 H 0.5927 0.0739 -0.0614 0.031 Uiso 1 1 calc R . . C17 C -0.0643(3) 0.3410(2) 0.24491(13) 0.0164(5) Uani 1 1 d . . . C18 C 0.1336(3) 0.2453(3) 0.31478(14) 0.0179(5) Uani 1 1 d . . . C19 C -0.1076(3) 0.1564(3) 0.35263(15) 0.0190(5) Uani 1 1 d . . . C20 C -0.1896(3) 0.0861(3) 0.31572(16) 0.0259(6) Uani 1 1 d . . . H20 H -0.1863 0.0966 0.2595 0.031 Uiso 1 1 calc R . . C21 C -0.2760(3) 0.0006(3) 0.36187(19) 0.0348(7) Uani 1 1 d . . . H21 H -0.3331 -0.0471 0.3371 0.042 Uiso 1 1 calc R . . C22 C -0.2804(3) -0.0164(3) 0.44354(18) 0.0339(7) Uani 1 1 d . . . H22 H -0.3399 -0.0756 0.4747 0.041 Uiso 1 1 calc R . . C23 C -0.1977(3) 0.0534(3) 0.47962(17) 0.0295(6) Uani 1 1 d . . . H23 H -0.1998 0.0411 0.5357 0.035 Uiso 1 1 calc R . . C24 C -0.1117(3) 0.1413(3) 0.43479(15) 0.0232(5) Uani 1 1 d . . . H24 H -0.0565 0.1905 0.4599 0.028 Uiso 1 1 calc R . . N1 N 0.2031(2) 0.3578(2) 0.09147(12) 0.0191(4) Uani 1 1 d . . . N2 N 0.3551(2) 0.3555(2) 0.10489(12) 0.0193(4) Uani 1 1 d . . . N3 N 0.3718(2) 0.3072(2) -0.02212(12) 0.0194(4) Uani 1 1 d . . . N4 N 0.0499(2) 0.4124(2) 0.22120(12) 0.0175(4) Uani 1 1 d . . . N5 N 0.1797(2) 0.3404(2) 0.25673(12) 0.0177(4) Uani 1 1 d . . . N6 N -0.0160(2) 0.2444(2) 0.30504(12) 0.0167(4) Uani 1 1 d . . . O1 O 0.2733(2) 0.52295(19) 0.30369(10) 0.0233(4) Uani 1 1 d . . . O2 O 0.10705(19) 0.33781(19) -0.02226(10) 0.0231(4) Uani 1 1 d . . . O3 O 0.59060(18) 0.34190(19) 0.01814(10) 0.0231(4) Uani 1 1 d . . . O4 O -0.18382(18) 0.36344(19) 0.21927(10) 0.0228(4) Uani 1 1 d . . . O5 O 0.2055(2) 0.1751(2) 0.36307(11) 0.0260(4) Uani 1 1 d . . . C25 C -0.1260(3) 0.1393(3) 0.07490(17) 0.0290(6) Uani 1 1 d . . . H25A H -0.1745 0.2353 0.0992 0.035 Uiso 1 1 calc R . . H25B H -0.1032 0.1533 0.0159 0.035 Uiso 1 1 calc R . . Cl1 Cl 0.04947(8) 0.05906(8) 0.10984(4) 0.03355(19) Uani 1 1 d . . . Cl2 Cl -0.25567(9) 0.02793(8) 0.10042(5) 0.0390(2) Uani 1 1 d . . . C26 C 0.2890(5) 0.4255(6) 0.4974(3) 0.0793(14) Uani 1 1 d DU . . H26A H 0.2432 0.3810 0.4609 0.095 Uiso 0.683(7) 1 calc PR A 1 H26B H 0.2977 0.5214 0.4744 0.095 Uiso 0.683(7) 1 calc PR A 1 Cl3 Cl 0.47282(16) 0.31761(15) 0.50289(12) 0.0554(7) Uani 0.683(7) 1 d PDU A 1 Cl4 Cl 0.1668(2) 0.4480(2) 0.59080(12) 0.0624(7) Uani 0.683(7) 1 d PDU A 1 H26X H 0.2735 0.3530 0.4656 0.075 Uiso 0.317(7) 1 d PR A 2 H26Y H 0.2981 0.5064 0.4616 0.075 Uiso 0.317(7) 1 d PR A 2 Cl3X Cl 0.4636(17) 0.355(3) 0.5208(16) 0.421(14) Uani 0.317(7) 1 d PDU A 2 Cl4X Cl 0.139(2) 0.4764(19) 0.5670(13) 0.358(12) Uani 0.317(7) 1 d PDU A 2 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 0.0122(11) 0.0216(12) 0.0189(12) 0.0027(9) -0.0029(9) -0.0035(9) C2 0.0154(11) 0.0213(12) 0.0243(12) 0.0061(10) -0.0035(9) -0.0068(9) C3 0.0137(11) 0.0230(12) 0.0204(12) -0.0010(9) -0.0010(9) -0.0086(9) C4 0.0120(11) 0.0228(12) 0.0200(12) -0.0010(9) -0.0026(9) -0.0072(9) C5 0.0117(11) 0.0290(13) 0.0263(13) -0.0007(10) -0.0053(10) -0.0048(10) C6 0.0245(13) 0.0194(12) 0.0321(14) 0.0006(10) -0.0014(11) -0.0064(10) C7 0.0226(13) 0.0224(13) 0.0313(14) -0.0037(11) 0.0014(11) -0.0065(10) C8 0.0408(17) 0.0335(16) 0.0353(16) -0.0131(13) -0.0027(13) -0.0046(13) C9 0.0142(11) 0.0194(12) 0.0210(12) 0.0009(9) -0.0024(9) -0.0054(9) C10 0.0155(11) 0.0188(11) 0.0195(12) -0.0004(9) -0.0033(9) -0.0037(9) C11 0.0163(11) 0.0226(12) 0.0228(12) -0.0024(9) -0.0017(9) -0.0097(9) C12 0.0210(13) 0.0274(13) 0.0265(13) -0.0002(10) -0.0052(10) -0.0072(10) C13 0.0307(15) 0.0464(17) 0.0259(14) -0.0006(12) -0.0064(12) -0.0172(13) C14 0.0250(14) 0.0537(19) 0.0320(16) -0.0203(14) 0.0026(12) -0.0160(13) C15 0.0178(13) 0.0346(15) 0.0441(17) -0.0147(13) -0.0028(12) -0.0041(11) C16 0.0192(12) 0.0271(13) 0.0319(14) -0.0024(11) -0.0075(11) -0.0062(10) C17 0.0128(11) 0.0200(11) 0.0155(11) -0.0018(9) -0.0007(9) -0.0035(9) C18 0.0139(11) 0.0209(12) 0.0192(12) -0.0006(9) -0.0014(9) -0.0063(9) C19 0.0125(11) 0.0197(12) 0.0241(12) 0.0033(9) -0.0012(9) -0.0059(9) C20 0.0233(13) 0.0310(14) 0.0278(14) 0.0042(11) -0.0085(11) -0.0133(11) C21 0.0291(15) 0.0357(16) 0.0472(18) 0.0061(13) -0.0113(13) -0.0202(13) C22 0.0243(14) 0.0336(15) 0.0437(17) 0.0116(13) -0.0004(12) -0.0154(12) C23 0.0249(14) 0.0348(15) 0.0267(14) 0.0074(11) -0.0002(11) -0.0098(11) C24 0.0190(12) 0.0283(13) 0.0233(13) 0.0004(10) -0.0037(10) -0.0082(10) N1 0.0092(9) 0.0256(11) 0.0238(11) -0.0010(8) -0.0038(8) -0.0061(8) N2 0.0089(9) 0.0303(11) 0.0210(10) -0.0022(8) -0.0031(8) -0.0083(8) N3 0.0137(10) 0.0244(11) 0.0201(10) -0.0015(8) -0.0021(8) -0.0053(8) N4 0.0090(9) 0.0237(10) 0.0198(10) 0.0047(8) -0.0044(7) -0.0044(8) N5 0.0089(9) 0.0237(10) 0.0229(10) 0.0065(8) -0.0069(8) -0.0071(8) N6 0.0107(9) 0.0207(10) 0.0195(10) 0.0030(8) -0.0030(7) -0.0061(8) O1 0.0226(9) 0.0252(9) 0.0225(9) -0.0037(7) -0.0042(7) -0.0063(7) O2 0.0166(9) 0.0286(9) 0.0255(9) 0.0002(7) -0.0074(7) -0.0060(7) O3 0.0107(8) 0.0324(10) 0.0262(9) -0.0005(7) -0.0012(7) -0.0074(7) O4 0.0111(8) 0.0301(10) 0.0285(9) 0.0048(7) -0.0072(7) -0.0065(7) O5 0.0168(9) 0.0350(10) 0.0285(10) 0.0127(8) -0.0099(7) -0.0098(8) C25 0.0270(14) 0.0283(14) 0.0352(15) 0.0016(11) -0.0115(12) -0.0097(11) Cl1 0.0234(3) 0.0394(4) 0.0371(4) 0.0028(3) -0.0077(3) -0.0061(3) Cl2 0.0360(4) 0.0438(4) 0.0445(4) 0.0010(3) -0.0083(3) -0.0225(3) C26 0.069(3) 0.092(4) 0.068(3) 0.007(3) -0.008(2) -0.012(3) Cl3 0.0324(8) 0.0367(8) 0.0946(13) -0.0054(7) -0.0064(7) -0.0076(5) Cl4 0.0616(11) 0.0567(10) 0.0604(11) -0.0251(7) 0.0147(7) -0.0138(7) Cl3X 0.260(13) 0.50(3) 0.53(3) 0.02(2) -0.250(17) -0.023(18) Cl4X 0.375(16) 0.207(14) 0.36(2) -0.011(13) 0.215(14) -0.059(13) _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 N4 1.447(3) . ? C1 N1 1.470(3) . ? C1 C2 1.550(3) . ? C2 C6 1.490(4) . ? C2 C3 1.535(3) . ? C3 N2 1.465(3) . ? C3 C4 1.544(3) . ? C4 O1 1.431(3) . ? C4 N5 1.476(3) . ? C4 C5 1.515(3) . ? C6 C7 1.324(4) . ? C7 O1 1.394(3) . ? C7 C8 1.486(4) . ? C9 O2 1.211(3) . ? C9 N1 1.378(3) . ? C9 N3 1.407(3) . ? C10 O3 1.210(3) . ? C10 N2 1.383(3) . ? C10 N3 1.401(3) . ? C11 C12 1.380(4) . ? C11 C16 1.392(4) . ? C11 N3 1.438(3) . ? C12 C13 1.392(4) . ? C13 C14 1.385(4) . ? C14 C15 1.376(4) . ? C15 C16 1.386(4) . ? C17 O4 1.215(3) . ? C17 N4 1.373(3) . ? C17 N6 1.388(3) . ? C18 O5 1.208(3) . ? C18 N5 1.375(3) . ? C18 N6 1.408(3) . ? C19 C20 1.388(3) . ? C19 C24 1.389(3) . ? C19 N6 1.439(3) . ? C20 C21 1.382(4) . ? C21 C22 1.381(4) . ? C22 C23 1.382(4) . ? C23 C24 1.387(4) . ? N1 N2 1.443(3) . ? N4 N5 1.427(3) . ? C25 Cl2 1.768(3) . ? C25 Cl1 1.779(3) . ? C26 Cl3 1.735(5) . ? C26 Cl4 1.739(5) . ? C26 Cl4X 1.609(11) . ? C26 Cl3X 1.670(11) . ? 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 C1 N1 108.96(19) . . ? N4 C1 C2 106.65(19) . . ? N1 C1 C2 102.84(18) . . ? C6 C2 C3 110.7(2) . . ? C6 C2 C1 116.5(2) . . ? C3 C2 C1 98.08(18) . . ? N2 C3 C2 103.82(18) . . ? N2 C3 C4 109.58(19) . . ? C2 C3 C4 108.48(19) . . ? O1 C4 N5 110.55(18) . . ? O1 C4 C5 106.83(19) . . ? N5 C4 C5 110.82(19) . . ? O1 C4 C3 109.36(19) . . ? N5 C4 C3 106.91(18) . . ? C5 C4 C3 112.41(19) . . ? C7 C6 C2 122.1(2) . . ? C6 C7 O1 123.0(2) . . ? C6 C7 C8 127.3(3) . . ? O1 C7 C8 109.6(2) . . ? O2 C9 N1 127.2(2) . . ? O2 C9 N3 127.8(2) . . ? N1 C9 N3 104.96(19) . . ? O3 C10 N2 127.3(2) . . ? O3 C10 N3 127.6(2) . . ? N2 C10 N3 105.13(19) . . ? C12 C11 C16 121.2(2) . . ? C12 C11 N3 120.0(2) . . ? C16 C11 N3 118.7(2) . . ? C11 C12 C13 119.1(2) . . ? C14 C13 C12 120.1(3) . . ? C15 C14 C13 120.2(3) . . ? C14 C15 C16 120.6(3) . . ? C15 C16 C11 118.7(3) . . ? O4 C17 N4 126.0(2) . . ? O4 C17 N6 128.5(2) . . ? N4 C17 N6 105.48(19) . . ? O5 C18 N5 128.0(2) . . ? O5 C18 N6 126.9(2) . . ? N5 C18 N6 105.06(19) . . ? C20 C19 C24 120.7(2) . . ? C20 C19 N6 119.6(2) . . ? C24 C19 N6 119.7(2) . . ? C21 C20 C19 119.1(2) . . ? C22 C21 C20 120.9(3) . . ? C21 C22 C23 119.6(2) . . ? C22 C23 C24 120.6(3) . . ? C23 C24 C19 119.1(2) . . ? C9 N1 N2 108.84(18) . . ? C9 N1 C1 126.85(19) . . ? N2 N1 C1 107.63(17) . . ? C10 N2 N1 108.16(18) . . ? C10 N2 C3 125.16(19) . . ? N1 N2 C3 107.52(17) . . ? C10 N3 C9 111.37(19) . . ? C10 N3 C11 124.63(19) . . ? C9 N3 C11 123.97(19) . . ? C17 N4 N5 108.46(18) . . ? C17 N4 C1 125.03(19) . . ? N5 N4 C1 114.45(17) . . ? C18 N5 N4 108.23(17) . . ? C18 N5 C4 129.38(19) . . ? N4 N5 C4 118.49(18) . . ? C17 N6 C18 111.35(19) . . ? C17 N6 C19 124.57(19) . . ? C18 N6 C19 124.07(19) . . ? C7 O1 C4 117.84(19) . . ? Cl2 C25 Cl1 110.38(15) . . ? Cl3 C26 Cl4 112.2(3) . . ? Cl3X C26 Cl4X 120.3(10) . . ? 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 N4 C1 C2 C6 -45.4(3) . . . . ? N1 C1 C2 C6 -159.9(2) . . . . ? N4 C1 C2 C3 72.7(2) . . . . ? N1 C1 C2 C3 -41.9(2) . . . . ? C6 C2 C3 N2 163.84(19) . . . . ? C1 C2 C3 N2 41.5(2) . . . . ? C6 C2 C3 C4 47.3(3) . . . . ? C1 C2 C3 C4 -75.0(2) . . . . ? N2 C3 C4 O1 -173.27(17) . . . . ? C2 C3 C4 O1 -60.5(2) . . . . ? N2 C3 C4 N5 -53.6(2) . . . . ? C2 C3 C4 N5 59.2(2) . . . . ? N2 C3 C4 C5 68.3(2) . . . . ? C2 C3 C4 C5 -179.02(19) . . . . ? C3 C2 C6 C7 -17.3(3) . . . . ? C1 C2 C6 C7 93.5(3) . . . . ? C2 C6 C7 O1 -2.9(4) . . . . ? C2 C6 C7 C8 175.0(3) . . . . ? C16 C11 C12 C13 1.7(4) . . . . ? N3 C11 C12 C13 -175.9(2) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C12 C13 C14 C15 -0.7(4) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? C12 C11 C16 C15 -1.5(4) . . . . ? N3 C11 C16 C15 176.1(2) . . . . ? C24 C19 C20 C21 0.1(4) . . . . ? N6 C19 C20 C21 179.3(2) . . . . ? C19 C20 C21 C22 -0.6(4) . . . . ? C20 C21 C22 C23 0.2(5) . . . . ? C21 C22 C23 C24 0.6(4) . . . . ? C22 C23 C24 C19 -1.1(4) . . . . ? C20 C19 C24 C23 0.7(4) . . . . ? N6 C19 C24 C23 -178.5(2) . . . . ? O2 C9 N1 N2 -176.9(2) . . . . ? N3 C9 N1 N2 5.8(2) . . . . ? O2 C9 N1 C1 -46.0(4) . . . . ? N3 C9 N1 C1 136.8(2) . . . . ? N4 C1 N1 C9 143.6(2) . . . . ? C2 C1 N1 C9 -103.5(2) . . . . ? N4 C1 N1 N2 -84.9(2) . . . . ? C2 C1 N1 N2 28.0(2) . . . . ? O3 C10 N2 N1 173.6(2) . . . . ? N3 C10 N2 N1 -8.7(2) . . . . ? O3 C10 N2 C3 45.4(4) . . . . ? N3 C10 N2 C3 -136.9(2) . . . . ? C9 N1 N2 C10 1.8(3) . . . . ? C1 N1 N2 C10 -138.84(19) . . . . ? C9 N1 N2 C3 139.5(2) . . . . ? C1 N1 N2 C3 -1.2(2) . . . . ? C2 C3 N2 C10 102.0(2) . . . . ? C4 C3 N2 C10 -142.3(2) . . . . ? C2 C3 N2 N1 -26.5(2) . . . . ? C4 C3 N2 N1 89.2(2) . . . . ? O3 C10 N3 C9 -169.4(2) . . . . ? N2 C10 N3 C9 12.8(3) . . . . ? O3 C10 N3 C11 12.6(4) . . . . ? N2 C10 N3 C11 -165.2(2) . . . . ? O2 C9 N3 C10 171.1(2) . . . . ? N1 C9 N3 C10 -11.7(3) . . . . ? O2 C9 N3 C11 -10.9(4) . . . . ? N1 C9 N3 C11 166.3(2) . . . . ? C12 C11 N3 C10 -126.9(3) . . . . ? C16 C11 N3 C10 55.5(3) . . . . ? C12 C11 N3 C9 55.3(3) . . . . ? C16 C11 N3 C9 -122.3(3) . . . . ? O4 C17 N4 N5 -171.6(2) . . . . ? N6 C17 N4 N5 10.5(2) . . . . ? O4 C17 N4 C1 -31.6(4) . . . . ? N6 C17 N4 C1 150.6(2) . . . . ? N1 C1 N4 C17 -86.6(3) . . . . ? C2 C1 N4 C17 163.1(2) . . . . ? N1 C1 N4 N5 51.5(2) . . . . ? C2 C1 N4 N5 -58.9(2) . . . . ? O5 C18 N5 N4 -172.2(2) . . . . ? N6 C18 N5 N4 9.0(2) . . . . ? O5 C18 N5 C4 -15.3(4) . . . . ? N6 C18 N5 C4 165.9(2) . . . . ? C17 N4 N5 C18 -12.6(3) . . . . ? C1 N4 N5 C18 -157.3(2) . . . . ? C17 N4 N5 C4 -172.42(19) . . . . ? C1 N4 N5 C4 42.8(3) . . . . ? O1 C4 N5 C18 -76.6(3) . . . . ? C5 C4 N5 C18 41.7(3) . . . . ? C3 C4 N5 C18 164.5(2) . . . . ? O1 C4 N5 N4 78.4(2) . . . . ? C5 C4 N5 N4 -163.34(19) . . . . ? C3 C4 N5 N4 -40.5(3) . . . . ? O4 C17 N6 C18 177.1(2) . . . . ? N4 C17 N6 C18 -5.0(3) . . . . ? O4 C17 N6 C19 -4.0(4) . . . . ? N4 C17 N6 C19 173.8(2) . . . . ? O5 C18 N6 C17 178.6(2) . . . . ? N5 C18 N6 C17 -2.6(3) . . . . ? O5 C18 N6 C19 -0.2(4) . . . . ? N5 C18 N6 C19 178.6(2) . . . . ? C20 C19 N6 C17 43.7(3) . . . . ? C24 C19 N6 C17 -137.1(2) . . . . ? C20 C19 N6 C18 -137.6(2) . . . . ? C24 C19 N6 C18 41.6(3) . . . . ? C6 C7 O1 C4 -10.9(4) . . . . ? C8 C7 O1 C4 170.8(2) . . . . ? N5 C4 O1 C7 -74.7(2) . . . . ? C5 C4 O1 C7 164.6(2) . . . . ? C3 C4 O1 C7 42.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.521 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.072