# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global #TrackingRef '- cif.cif' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Shan Gao' _publ_contact_author_address ; Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080 CHINA ; _publ_contact_author_email shangao67@yahoo.com _publ_section_title ; Inorganic anion induced supramolecular architectures and luminescent properties of flexible bis(pyridyl) based ionic salts ; loop_ _publ_author_name 'Zhao-Peng Deng' 'Hui-Ling Qi' 'Li-Hua Huo' 'Hui Zhao' 'Shan Gao' data_complex1 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(N O3)' _chemical_formula_sum 'C18 H20 N6 O6' _chemical_formula_weight 416.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9451(16) _cell_length_b 8.6039(17) _cell_length_c 8.7100(17) _cell_angle_alpha 64.75(3) _cell_angle_beta 73.33(3) _cell_angle_gamma 63.46(3) _cell_volume 478.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1505 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 27.41 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9727 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4710 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2174 _reflns_number_gt 1245 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.1307P] 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 2174 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1490 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8339(5) -0.1580(4) 0.1855(4) 0.1033(11) Uani 1 1 d . . . O2 O 0.7506(5) -0.3164(4) 0.4370(4) 0.0991(10) Uani 1 1 d . . . O3 O 0.8255(4) -0.4197(3) 0.2328(3) 0.0848(9) Uani 1 1 d . . . N1 N 0.7534(4) 0.2672(3) 0.4891(3) 0.0542(7) Uani 1 1 d . . . H1N H 0.7711 0.3564 0.3996 0.065 Uiso 1 1 calc R . . N2 N 0.8217(4) 0.0947(3) 0.3180(3) 0.0523(7) Uani 1 1 d . . . H2N H 0.8418 -0.0109 0.3150 0.063 Uiso 1 1 calc R . . N3 N 0.8049(4) -0.2975(4) 0.2868(4) 0.0671(8) Uani 1 1 d . . . C1 C 0.7716(4) 0.1127(4) 0.4707(4) 0.0448(7) Uani 1 1 d . . . C2 C 0.7382(4) -0.0295(4) 0.6196(4) 0.0533(8) Uani 1 1 d . . . H2 H 0.7490 -0.1383 0.6120 0.064 Uiso 1 1 calc R . . C3 C 0.6904(5) -0.0081(5) 0.7739(4) 0.0622(9) Uani 1 1 d . . . H3 H 0.6679 -0.1020 0.8717 0.075 Uiso 1 1 calc R . . C4 C 0.6749(5) 0.1535(5) 0.7863(4) 0.0693(10) Uani 1 1 d . . . H4 H 0.6421 0.1693 0.8916 0.083 Uiso 1 1 calc R . . C5 C 0.7085(5) 0.2866(5) 0.6425(4) 0.0636(9) Uani 1 1 d . . . H5 H 0.7005 0.3947 0.6495 0.076 Uiso 1 1 calc R . . C6 C 0.8458(5) 0.2378(4) 0.1551(4) 0.0516(8) Uani 1 1 d . . . H6A H 0.9309 0.1782 0.0742 0.062 Uiso 1 1 calc R . . H6B H 0.9057 0.3053 0.1715 0.062 Uiso 1 1 calc R . . C7 C 0.6647(4) 0.3743(4) 0.0785(4) 0.0434(7) Uani 1 1 d . . . C8 C 0.6719(5) 0.5117(4) -0.0792(4) 0.0506(8) Uani 1 1 d . . . H8 H 0.7879 0.5210 -0.1340 0.061 Uiso 1 1 calc R . . C9 C 0.4902(5) 0.3651(4) 0.1563(4) 0.0497(8) Uani 1 1 d . . . H9 H 0.4816 0.2744 0.2625 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.162(3) 0.089(2) 0.085(2) -0.0428(16) 0.0328(19) -0.085(2) O2 0.158(3) 0.091(2) 0.0588(17) -0.0344(15) 0.0081(18) -0.060(2) O3 0.114(2) 0.0815(18) 0.0861(19) -0.0487(15) 0.0129(16) -0.0552(17) N1 0.0668(19) 0.0513(15) 0.0497(16) -0.0214(12) -0.0005(13) -0.0268(14) N2 0.0662(19) 0.0460(14) 0.0497(16) -0.0213(12) -0.0066(13) -0.0209(13) N3 0.076(2) 0.0648(19) 0.073(2) -0.0384(17) 0.0098(16) -0.0344(16) C1 0.0402(18) 0.0494(17) 0.0479(18) -0.0217(14) -0.0070(13) -0.0136(14) C2 0.057(2) 0.0546(19) 0.056(2) -0.0196(16) -0.0074(16) -0.0265(16) C3 0.069(3) 0.067(2) 0.050(2) -0.0141(17) -0.0023(17) -0.0336(19) C4 0.086(3) 0.081(3) 0.053(2) -0.0368(19) 0.0065(19) -0.038(2) C5 0.077(3) 0.065(2) 0.060(2) -0.0328(18) 0.0003(18) -0.0303(19) C6 0.056(2) 0.0572(19) 0.0449(18) -0.0232(15) 0.0023(15) -0.0237(17) C7 0.0469(19) 0.0471(17) 0.0439(17) -0.0229(13) -0.0040(14) -0.0183(15) C8 0.047(2) 0.0593(19) 0.0485(19) -0.0221(15) 0.0058(15) -0.0261(16) C9 0.055(2) 0.0527(18) 0.0418(17) -0.0147(14) 0.0001(15) -0.0258(16) _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 1.225(4) . ? O2 N3 1.217(4) . ? O3 N3 1.255(3) . ? N1 C5 1.344(4) . ? N1 C1 1.345(4) . ? N1 H1N 0.8600 . ? N2 C1 1.330(4) . ? N2 C6 1.460(4) . ? N2 H2N 0.8600 . ? C1 C2 1.410(4) . ? C2 C3 1.357(4) . ? C2 H2 0.9300 . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.345(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.506(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.379(4) . ? C7 C8 1.384(4) . ? C8 C9 1.379(4) 2_665 ? C8 H8 0.9300 . ? C9 C8 1.379(4) 2_665 ? C9 H9 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 122.2(3) . . ? C5 N1 H1N 118.9 . . ? C1 N1 H1N 118.9 . . ? C1 N2 C6 125.9(2) . . ? C1 N2 H2N 117.0 . . ? C6 N2 H2N 117.0 . . ? O2 N3 O1 121.1(3) . . ? O2 N3 O3 119.8(3) . . ? O1 N3 O3 119.1(3) . . ? N2 C1 N1 121.0(3) . . ? N2 C1 C2 121.6(3) . . ? N1 C1 C2 117.4(3) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 118.5(3) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 121.6(3) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? N2 C6 C7 114.6(3) . . ? N2 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C9 C7 C8 117.9(3) . . ? C9 C7 C6 122.7(3) . . ? C8 C7 C6 119.4(3) . . ? C9 C8 C7 121.1(3) 2_665 . ? C9 C8 H8 119.5 2_665 . ? C7 C8 H8 119.5 . . ? C7 C9 C8 121.0(3) . 2_665 ? C7 C9 H9 119.5 . . ? C8 C9 H9 119.5 2_665 . ? 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 N2 C1 N1 -5.8(5) . . . . ? C6 N2 C1 C2 175.1(3) . . . . ? C5 N1 C1 N2 -178.0(3) . . . . ? C5 N1 C1 C2 1.1(4) . . . . ? N2 C1 C2 C3 178.9(3) . . . . ? N1 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 0.0(5) . . . . ? C1 N1 C5 C4 -1.6(5) . . . . ? C3 C4 C5 N1 1.0(6) . . . . ? C1 N2 C6 C7 -82.3(4) . . . . ? N2 C6 C7 C9 0.2(4) . . . . ? N2 C6 C7 C8 -177.6(2) . . . . ? C9 C7 C8 C9 -0.3(5) . . . 2_665 ? C6 C7 C8 C9 177.6(2) . . . 2_665 ? C8 C7 C9 C8 0.3(5) . . . 2_665 ? C6 C7 C9 C8 -177.5(3) . . . 2_665 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.86 2.00 2.843(4) 166.0 1_565 N2 H2N O1 0.86 2.05 2.821(4) 148.5 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.216 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.050 #===END data_complex2 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(N O3)' _chemical_formula_sum 'C18 H20 N6 O6' _chemical_formula_weight 416.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0087(10) _cell_length_b 15.303(4) _cell_length_c 12.989(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.44(3) _cell_angle_gamma 90.00 _cell_volume 949.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4980 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.42 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9769 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7046 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2168 _reflns_number_gt 1133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.5179P] 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 2168 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0903(5) 0.42303(14) 0.87966(18) 0.0749(8) Uani 1 1 d . . . O2 O 0.1446(6) 0.39141(17) 0.77207(18) 0.0785(8) Uani 1 1 d . . . O3 O -0.1434(6) 0.29796(14) 0.8034(2) 0.0904(9) Uani 1 1 d . . . N1 N 0.6137(5) 0.14676(14) 0.50629(18) 0.0519(7) Uani 1 1 d . . . H1N H 0.6913 0.1378 0.4565 0.062 Uiso 1 1 calc R . . N2 N 0.1387(5) 0.30079(13) 0.56893(18) 0.0513(7) Uani 1 1 d . . . H2N H 0.0563 0.3055 0.6180 0.062 Uiso 1 1 calc R . . N3 N -0.0296(6) 0.37007(15) 0.81692(19) 0.0539(7) Uani 1 1 d . . . C1 C 0.4501(6) 0.21777(16) 0.4981(2) 0.0450(8) Uani 1 1 d . . . H1A H 0.4259 0.2562 0.4405 0.054 Uiso 1 1 calc R . . C2 C 0.3180(6) 0.23329(15) 0.5760(2) 0.0408(7) Uani 1 1 d . . . C3 C 0.3719(7) 0.17380(17) 0.6619(2) 0.0549(9) Uani 1 1 d . . . H3A H 0.2908 0.1827 0.7167 0.066 Uiso 1 1 calc R . . C4 C 0.5406(7) 0.10333(19) 0.6666(3) 0.0648(10) Uani 1 1 d . . . H4A H 0.5731 0.0644 0.7240 0.078 Uiso 1 1 calc R . . C5 C 0.6621(7) 0.08982(19) 0.5869(3) 0.0633(9) Uani 1 1 d . . . H5A H 0.7767 0.0416 0.5890 0.076 Uiso 1 1 calc R . . C6 C 0.0777(6) 0.36516(16) 0.4840(2) 0.0501(8) Uani 1 1 d . . . H6A H -0.0943 0.3948 0.4828 0.060 Uiso 1 1 calc R . . H6B H 0.0447 0.3351 0.4156 0.060 Uiso 1 1 calc R . . C7 C 0.4917(6) 0.45564(16) 0.5914(2) 0.0477(8) Uani 1 1 d . . . H7A H 0.4884 0.4262 0.6537 0.057 Uiso 1 1 calc R . . C8 C 0.3021(6) 0.43310(15) 0.4930(2) 0.0426(7) Uani 1 1 d . . . C9 C 0.3146(6) 0.47853(16) 0.4021(2) 0.0468(8) Uani 1 1 d . . . H9A H 0.1899 0.4644 0.3353 0.056 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 0.086(2) 0.0705(14) 0.0856(16) -0.0183(12) 0.0523(15) -0.0133(12) O2 0.075(2) 0.1086(18) 0.0632(14) 0.0029(13) 0.0382(14) 0.0064(15) O3 0.096(2) 0.0529(12) 0.0993(19) -0.0014(12) -0.0057(15) -0.0130(12) N1 0.0432(19) 0.0553(13) 0.0606(14) -0.0074(11) 0.0209(12) 0.0041(11) N2 0.0561(19) 0.0453(12) 0.0647(15) -0.0022(10) 0.0364(13) 0.0026(11) N3 0.053(2) 0.0556(14) 0.0474(13) 0.0000(11) 0.0070(13) 0.0020(12) C1 0.042(2) 0.0463(13) 0.0490(15) -0.0007(11) 0.0175(13) -0.0003(12) C2 0.037(2) 0.0406(12) 0.0463(14) -0.0054(10) 0.0155(12) -0.0058(11) C3 0.065(2) 0.0545(15) 0.0484(16) 0.0006(12) 0.0215(14) -0.0061(15) C4 0.069(3) 0.0560(17) 0.066(2) 0.0148(14) 0.0152(18) -0.0029(16) C5 0.054(3) 0.0506(16) 0.079(2) 0.0046(15) 0.0112(18) 0.0076(14) C6 0.045(2) 0.0425(13) 0.0640(17) -0.0009(12) 0.0185(14) 0.0024(12) C7 0.049(2) 0.0485(14) 0.0466(15) 0.0023(11) 0.0152(13) 0.0035(13) C8 0.039(2) 0.0396(12) 0.0504(14) -0.0021(10) 0.0147(13) 0.0065(11) C9 0.044(2) 0.0512(14) 0.0408(14) -0.0035(11) 0.0064(12) 0.0006(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 O1 N3 1.250(3) . ? O2 N3 1.229(3) . ? O3 N3 1.230(3) . ? N1 C5 1.327(4) . ? N1 C1 1.346(3) . ? N1 H1N 0.8600 . ? N2 C2 1.354(3) . ? N2 C6 1.442(3) . ? N2 H2N 0.8600 . ? C1 C2 1.386(4) . ? C1 H1A 0.9300 . ? C2 C3 1.402(4) . ? C3 C4 1.360(4) . ? C3 H3A 0.9300 . ? C4 C5 1.365(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C8 1.510(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.384(4) 3_666 ? C7 C8 1.389(4) . ? C7 H7A 0.9300 . ? C8 C9 1.387(3) . ? C9 C7 1.384(4) 3_666 ? C9 H9A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 123.8(3) . . ? C5 N1 H1N 118.1 . . ? C1 N1 H1N 118.1 . . ? C2 N2 C6 123.9(2) . . ? C2 N2 H2N 118.1 . . ? C6 N2 H2N 118.1 . . ? O2 N3 O3 122.3(3) . . ? O2 N3 O1 118.9(2) . . ? O3 N3 O1 118.8(3) . . ? N1 C1 C2 119.5(2) . . ? N1 C1 H1A 120.2 . . ? C2 C1 H1A 120.2 . . ? N2 C2 C1 122.3(2) . . ? N2 C2 C3 121.0(2) . . ? C1 C2 C3 116.7(2) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? N1 C5 C4 118.8(3) . . ? N1 C5 H5A 120.6 . . ? C4 C5 H5A 120.6 . . ? N2 C6 C8 115.4(2) . . ? N2 C6 H6A 108.4 . . ? C8 C6 H6A 108.4 . . ? N2 C6 H6B 108.4 . . ? C8 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C9 C7 C8 120.7(2) 3_666 . ? C9 C7 H7A 119.7 3_666 . ? C8 C7 H7A 119.7 . . ? C9 C8 C7 117.8(2) . . ? C9 C8 C6 120.1(2) . . ? C7 C8 C6 122.0(2) . . ? C7 C9 C8 121.5(2) 3_666 . ? C7 C9 H9A 119.2 3_666 . ? C8 C9 H9A 119.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -1.2(4) . . . . ? C6 N2 C2 C1 -3.2(4) . . . . ? C6 N2 C2 C3 178.8(3) . . . . ? N1 C1 C2 N2 -176.2(2) . . . . ? N1 C1 C2 C3 1.9(4) . . . . ? N2 C2 C3 C4 176.6(3) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C1 N1 C5 C4 -0.1(4) . . . . ? C3 C4 C5 N1 0.5(5) . . . . ? C2 N2 C6 C8 -75.9(3) . . . . ? C9 C7 C8 C9 0.2(4) 3_666 . . . ? C9 C7 C8 C6 -176.5(2) 3_666 . . . ? N2 C6 C8 C9 158.1(2) . . . . ? N2 C6 C8 C7 -25.4(4) . . . . ? C7 C8 C9 C7 -0.2(4) . . . 3_666 ? C6 C8 C9 C7 176.6(2) . . . 3_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.86 1.93 2.740(3) 157.2 4_665 N2 H2N O2 0.86 2.32 2.973(3) 132.6 . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.257 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.053 #===END data_complex3 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(N O3)' _chemical_formula_sum 'C18 H20 N6 O6' _chemical_formula_weight 416.40 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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' '-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 14.556(3) _cell_length_b 9.1625(18) _cell_length_c 16.157(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.29(3) _cell_angle_gamma 90.00 _cell_volume 1932.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5550 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 27.43 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9133 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2196 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.1041P] 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 2196 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1867 _refine_ls_wR_factor_gt 0.1586 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.65187(13) 0.1067(2) 0.08379(17) 0.0912(7) Uani 1 1 d . . . O2 O 0.80542(15) 0.1711(3) 0.11597(18) 0.1051(8) Uani 1 1 d . . . O3 O 0.75926(16) -0.0466(3) 0.0786(2) 0.1287(11) Uani 1 1 d . . . N1 N 0.62633(12) 0.4010(2) 0.12152(12) 0.0508(5) Uani 1 1 d . . . H1N H 0.6253 0.3084 0.1124 0.061 Uiso 1 1 calc R . . N2 N 0.45194(12) 0.39279(19) 0.08455(12) 0.0477(5) Uani 1 1 d . . . H2N H 0.3968 0.4421 0.0711 0.057 Uiso 1 1 calc R . . N3 N 0.73887(15) 0.0772(3) 0.09199(17) 0.0690(6) Uani 1 1 d . . . C1 C 0.53907(14) 0.4680(2) 0.11104(13) 0.0425(5) Uani 1 1 d . . . C2 C 0.54251(17) 0.6197(2) 0.12636(15) 0.0515(6) Uani 1 1 d . . . H2 H 0.4838 0.6693 0.1194 0.062 Uiso 1 1 calc R . . C3 C 0.63206(18) 0.6934(3) 0.15138(17) 0.0607(6) Uani 1 1 d . . . H3 H 0.6345 0.7934 0.1619 0.073 Uiso 1 1 calc R . . C4 C 0.71988(18) 0.6202(3) 0.16128(18) 0.0677(7) Uani 1 1 d . . . H4 H 0.7810 0.6707 0.1782 0.081 Uiso 1 1 calc R . . C5 C 0.71547(17) 0.4748(3) 0.14601(18) 0.0628(7) Uani 1 1 d . . . H5 H 0.7739 0.4249 0.1523 0.075 Uiso 1 1 calc R . . C6 C 0.44229(15) 0.2358(2) 0.07660(14) 0.0473(5) Uani 1 1 d . . . H6A H 0.4838 0.2003 0.0476 0.057 Uiso 1 1 calc R . . H6B H 0.3715 0.2116 0.0363 0.057 Uiso 1 1 calc R . . C7 C 0.5000 0.2305(3) 0.2500 0.0423(7) Uani 1 2 d S . . H7 H 0.5000 0.3320 0.2500 0.051 Uiso 1 2 calc SR . . C8 C 0.47418(13) 0.1569(2) 0.16767(14) 0.0416(5) Uani 1 1 d . . . C9 C 0.47440(15) 0.0054(2) 0.16832(15) 0.0504(6) Uani 1 1 d . . . H9 H 0.4573 -0.0461 0.1139 0.060 Uiso 1 1 calc R . . C10 C 0.5000 -0.0685(3) 0.2500 0.0556(8) Uani 1 2 d S . . H10 H 0.5000 -0.1700 0.2500 0.067 Uiso 1 2 calc SR . . 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 0.0536(10) 0.0848(15) 0.1422(19) -0.0240(12) 0.0497(11) 0.0061(9) O2 0.0711(13) 0.0855(15) 0.163(2) -0.0222(14) 0.0552(14) -0.0117(12) O3 0.0742(13) 0.0792(15) 0.243(3) -0.0581(18) 0.0803(17) -0.0027(11) N1 0.0433(10) 0.0505(11) 0.0590(11) 0.0014(8) 0.0229(9) 0.0044(7) N2 0.0395(9) 0.0486(10) 0.0554(11) 0.0054(8) 0.0214(8) 0.0042(7) N3 0.0491(11) 0.0684(14) 0.0909(16) -0.0171(12) 0.0322(11) 0.0028(10) C1 0.0393(10) 0.0495(12) 0.0401(10) 0.0020(9) 0.0189(8) 0.0023(8) C2 0.0521(12) 0.0516(13) 0.0563(13) -0.0030(10) 0.0289(11) 0.0032(10) C3 0.0633(14) 0.0551(14) 0.0677(15) -0.0115(11) 0.0326(12) -0.0084(11) C4 0.0494(13) 0.0751(18) 0.0795(18) -0.0122(13) 0.0295(13) -0.0163(12) C5 0.0420(12) 0.0705(17) 0.0763(16) -0.0032(13) 0.0267(11) 0.0014(11) C6 0.0451(11) 0.0466(12) 0.0504(12) -0.0020(9) 0.0213(10) -0.0023(9) C7 0.0373(13) 0.0411(15) 0.0501(16) 0.000 0.0210(12) 0.000 C8 0.0333(9) 0.0445(11) 0.0500(12) -0.0015(9) 0.0213(9) -0.0010(8) C9 0.0525(12) 0.0458(12) 0.0564(13) -0.0066(9) 0.0273(11) -0.0028(9) C10 0.066(2) 0.0414(16) 0.066(2) 0.000 0.0343(16) 0.000 _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 1.243(2) . ? O2 N3 1.223(3) . ? O3 N3 1.216(3) . ? N1 C1 1.352(2) . ? N1 C5 1.357(3) . ? N1 H1N 0.8600 . ? N2 C1 1.336(2) . ? N2 C6 1.445(3) . ? N2 H2N 0.8600 . ? C1 C2 1.409(3) . ? C2 C3 1.361(3) . ? C2 H2 0.9300 . ? C3 C4 1.389(3) . ? C3 H3 0.9300 . ? C4 C5 1.352(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.516(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.387(2) . ? C7 C8 1.387(2) 2_655 ? C7 H7 0.9300 . ? C8 C9 1.388(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C9 1.380(3) 2_655 ? C10 H10 0.9300 . ? 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 C5 122.27(19) . . ? C1 N1 H1N 118.9 . . ? C5 N1 H1N 118.9 . . ? C1 N2 C6 125.65(17) . . ? C1 N2 H2N 117.2 . . ? C6 N2 H2N 117.2 . . ? O3 N3 O2 119.4(2) . . ? O3 N3 O1 120.1(2) . . ? O2 N3 O1 120.5(2) . . ? N2 C1 N1 120.76(19) . . ? N2 C1 C2 121.33(18) . . ? N1 C1 C2 117.89(18) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.4(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 N1 120.4(2) . . ? C4 C5 H5 119.8 . . ? N1 C5 H5 119.8 . . ? N2 C6 C8 114.36(17) . . ? N2 C6 H6A 108.7 . . ? C8 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C8 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C8 121.8(3) . 2_655 ? C8 C7 H7 119.1 . . ? C8 C7 H7 119.1 2_655 . ? C7 C8 C9 118.7(2) . . ? C7 C8 C6 122.35(19) . . ? C9 C8 C6 118.89(19) . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C9 121.2(3) 2_655 . ? C9 C10 H10 119.4 2_655 . ? C9 C10 H10 119.4 . . ? 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 N2 C1 N1 8.9(3) . . . . ? C6 N2 C1 C2 -172.96(19) . . . . ? C5 N1 C1 N2 178.3(2) . . . . ? C5 N1 C1 C2 0.0(3) . . . . ? N2 C1 C2 C3 -178.6(2) . . . . ? N1 C1 C2 C3 -0.4(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 N1 -0.2(4) . . . . ? C1 N1 C5 C4 0.2(3) . . . . ? C1 N2 C6 C8 78.7(2) . . . . ? C8 C7 C8 C9 -0.01(13) 2_655 . . . ? C8 C7 C8 C6 177.86(18) 2_655 . . . ? N2 C6 C8 C7 6.4(2) . . . . ? N2 C6 C8 C9 -175.70(17) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C6 C8 C9 C10 -177.93(14) . . . . ? C8 C9 C10 C9 -0.01(13) . . . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.86 1.98 2.825(3) 165.6 . N2 H2N O3 0.86 2.06 2.819(3) 146.4 3_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.289 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.049 #===END data_complex4 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(N O3)' _chemical_formula_sum 'C18 H20 N6 O6' _chemical_formula_weight 416.40 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' _symmetry_space_group_name_Hall '-P 2yn' 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 8.2787(17) _cell_length_b 16.705(3) _cell_length_c 13.977(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.07(3) _cell_angle_gamma 90.00 _cell_volume 1913.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4742 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14158 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0978 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3359 _reflns_number_gt 2027 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.8967P] 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 3359 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1954 _refine_ls_R_factor_gt 0.0899 _refine_ls_wR_factor_ref 0.2192 _refine_ls_wR_factor_gt 0.1716 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7129(5) 0.7004(2) 0.5957(3) 0.1042(14) Uani 1 1 d . . . O2 O 0.7153(5) 0.5739(2) 0.5738(3) 0.1021(13) Uani 1 1 d . . . O3 O 0.5777(5) 0.6230(2) 0.6760(3) 0.1019(13) Uani 1 1 d . . . O4 O 0.0531(5) 0.6129(2) 0.7312(3) 0.0935(12) Uani 1 1 d . . . O5 O 0.1595(5) 0.7067(2) 0.6536(3) 0.0953(12) Uani 1 1 d . . . O6 O 0.1380(5) 0.5878(2) 0.5964(3) 0.0888(12) Uani 1 1 d . . . N1 N 0.3252(5) 0.6846(4) 0.4811(3) 0.0901(14) Uani 1 1 d . . . H1N H 0.2793 0.6795 0.5323 0.108 Uiso 1 1 calc R . . N2 N 0.4966(6) 0.5540(3) 0.3195(3) 0.0864(13) Uani 1 1 d . . . H2N H 0.4858 0.5099 0.3498 0.104 Uiso 1 1 calc R . . N3 N 0.3864(5) 0.7464(3) -0.0700(3) 0.0765(12) Uani 1 1 d . . . H3N H 0.3604 0.7593 -0.0146 0.092 Uiso 1 1 calc R . . N4 N 0.5438(6) 0.8534(4) -0.2659(4) 0.0695(14) Uani 1 1 d . . . H4N H 0.5860 0.8454 -0.3179 0.138 Uiso 1 1 calc R . . N5 N 0.6702(6) 0.6328(3) 0.6152(3) 0.0786(13) Uani 1 1 d . . . N6 N 0.1158(6) 0.6363(3) 0.6619(4) 0.0779(13) Uani 1 1 d . . . C1 C 0.3700(6) 0.6190(3) 0.4395(4) 0.0754(15) Uani 1 1 d . . . H1 H 0.3501 0.5694 0.4659 0.090 Uiso 1 1 calc R . . C2 C 0.4466(6) 0.6222(4) 0.3569(4) 0.0704(14) Uani 1 1 d . . . C3 C 0.4654(7) 0.6988(4) 0.3212(4) 0.0858(16) Uani 1 1 d . . . H3 H 0.5115 0.7053 0.2647 0.103 Uiso 1 1 calc R . . C4 C 0.4175(8) 0.7644(4) 0.3676(5) 0.100(2) Uani 1 1 d . . . H4 H 0.4339 0.8149 0.3428 0.120 Uiso 1 1 calc R . . C5 C 0.3466(8) 0.7581(4) 0.4489(6) 0.108(2) Uani 1 1 d . . . H5 H 0.3144 0.8031 0.4806 0.129 Uiso 1 1 calc R . . C6 C 0.5673(7) 0.5510(3) 0.2313(4) 0.0886(17) Uani 1 1 d . . . H6A H 0.6314 0.5024 0.2311 0.106 Uiso 1 1 calc R . . H6B H 0.6411 0.5960 0.2302 0.106 Uiso 1 1 calc R . . C7 C 0.4461(6) 0.5531(3) 0.1414(4) 0.0717(14) Uani 1 1 d . . . C8 C 0.4621(6) 0.6075(3) 0.0690(4) 0.0764(15) Uani 1 1 d . . . H8 H 0.5457 0.6451 0.0784 0.092 Uiso 1 1 calc R . . C9 C 0.3566(7) 0.6075(3) -0.0173(4) 0.0722(14) Uani 1 1 d . . . C10 C 0.2318(7) 0.5524(3) -0.0306(4) 0.0776(15) Uani 1 1 d . . . H10 H 0.1591 0.5522 -0.0877 0.093 Uiso 1 1 calc R . . C11 C 0.2147(6) 0.4970(3) 0.0416(4) 0.0761(15) Uani 1 1 d . . . H11 H 0.1308 0.4596 0.0330 0.091 Uiso 1 1 calc R . . C12 C 0.3214(7) 0.4979(3) 0.1246(4) 0.0739(14) Uani 1 1 d . . . H12 H 0.3100 0.4600 0.1719 0.089 Uiso 1 1 calc R . . C13 C 0.3830(7) 0.6635(3) -0.0978(4) 0.0837(16) Uani 1 1 d . . . H13A H 0.4854 0.6501 -0.1202 0.100 Uiso 1 1 calc R . . H13B H 0.2964 0.6555 -0.1513 0.100 Uiso 1 1 calc R . . C14 C 0.4935(6) 0.7887(3) -0.2134(4) 0.0697(14) Uani 1 1 d . . . H14 H 0.5027 0.7363 -0.2345 0.084 Uiso 1 1 calc R . . C15 C 0.4297(6) 0.8052(3) -0.1292(4) 0.0606(12) Uani 1 1 d . . . C16 C 0.4138(6) 0.8853(3) -0.1041(4) 0.0710(14) Uani 1 1 d . . . H16 H 0.3689 0.8979 -0.0486 0.085 Uiso 1 1 calc R . . C17 C 0.4600(5) 0.9421(3) -0.1560(3) 0.0490(11) Uani 1 1 d . . . H17 H 0.4455 0.9946 -0.1366 0.059 Uiso 1 1 calc R . . C18 C 0.5243(6) 0.9308(3) -0.2324(5) 0.0820(17) Uani 1 1 d . . . H18 H 0.5583 0.9743 -0.2659 0.098 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 0.133(4) 0.077(3) 0.108(3) 0.011(2) 0.034(3) -0.015(3) O2 0.122(4) 0.095(3) 0.095(3) -0.020(2) 0.034(3) -0.001(3) O3 0.127(4) 0.093(3) 0.097(3) 0.010(2) 0.054(3) 0.004(2) O4 0.120(3) 0.098(3) 0.066(2) -0.001(2) 0.025(2) -0.008(2) O5 0.111(3) 0.072(2) 0.103(3) -0.009(2) 0.017(2) -0.003(2) O6 0.102(3) 0.086(3) 0.082(3) -0.012(2) 0.025(2) -0.006(2) N1 0.081(3) 0.114(4) 0.075(3) -0.006(3) 0.008(2) -0.002(3) N2 0.112(4) 0.085(3) 0.062(3) 0.009(3) 0.012(3) -0.003(3) N3 0.090(3) 0.080(3) 0.061(3) 0.000(2) 0.016(2) 0.004(3) N4 0.070(4) 0.071(3) 0.062(4) 0.001(3) 0.009(3) 0.000(3) N5 0.079(3) 0.091(4) 0.066(3) 0.001(3) 0.012(3) 0.002(3) N6 0.078(3) 0.080(4) 0.073(4) -0.003(3) 0.002(3) 0.008(3) C1 0.066(4) 0.080(4) 0.075(4) 0.009(3) -0.004(3) -0.013(3) C2 0.064(3) 0.084(4) 0.061(3) 0.009(3) -0.001(3) -0.016(3) C3 0.071(4) 0.106(5) 0.079(4) 0.009(4) 0.007(3) -0.017(4) C4 0.095(5) 0.087(5) 0.119(6) 0.010(4) 0.018(4) -0.020(4) C5 0.103(5) 0.076(4) 0.144(7) -0.005(4) 0.016(5) -0.008(4) C6 0.075(4) 0.109(4) 0.079(4) -0.003(3) -0.001(3) 0.003(3) C7 0.061(3) 0.085(4) 0.070(4) 0.007(3) 0.012(3) 0.001(3) C8 0.063(3) 0.085(4) 0.081(4) -0.008(3) 0.009(3) -0.006(3) C9 0.070(4) 0.076(3) 0.069(4) -0.002(3) 0.005(3) -0.001(3) C10 0.070(4) 0.084(4) 0.075(4) -0.003(3) -0.002(3) 0.002(3) C11 0.059(3) 0.080(4) 0.089(4) 0.007(3) 0.006(3) -0.007(3) C12 0.069(4) 0.070(3) 0.084(4) 0.007(3) 0.016(3) 0.004(3) C13 0.105(5) 0.081(4) 0.064(4) -0.001(3) 0.006(3) -0.018(3) C14 0.072(4) 0.073(3) 0.064(4) 0.004(3) 0.011(3) 0.000(3) C15 0.053(3) 0.072(3) 0.056(3) 0.007(3) 0.003(2) -0.003(3) C16 0.066(3) 0.080(4) 0.064(3) -0.007(3) -0.002(3) 0.008(3) C17 0.049(3) 0.048(3) 0.052(3) 0.001(2) 0.014(2) 0.006(2) C18 0.066(4) 0.051(3) 0.125(6) 0.011(3) -0.001(4) 0.006(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 N5 1.224(5) . ? O2 N5 1.226(5) . ? O3 N5 1.232(5) . ? O4 N6 1.226(5) . ? O5 N6 1.241(5) . ? O6 N6 1.256(5) . ? N1 C1 1.318(6) . ? N1 C5 1.329(7) . ? N1 H1N 0.8600 . ? N2 C2 1.343(6) . ? N2 C6 1.438(6) . ? N2 H2N 0.8600 . ? N3 C15 1.365(6) . ? N3 C13 1.438(6) . ? N3 H3N 0.8600 . ? N4 C18 1.393(7) . ? N4 C14 1.402(6) . ? N4 H4N 0.8600 . ? C1 C2 1.394(7) . ? C1 H1 0.9300 . ? C2 C3 1.390(7) . ? C3 C4 1.361(8) . ? C3 H3 0.9300 . ? C4 C5 1.354(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.494(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.379(6) . ? C7 C8 1.381(7) . ? C8 C9 1.386(6) . ? C8 H8 0.9300 . ? C9 C10 1.377(7) . ? C9 C13 1.502(7) . ? C10 C11 1.391(7) . ? C10 H10 0.9300 . ? C11 C12 1.356(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C15 C16 1.395(6) . ? C16 C17 1.285(6) . ? C16 H16 0.9300 . ? C17 C18 1.272(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? 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 C5 124.1(6) . . ? C1 N1 H1N 117.9 . . ? C5 N1 H1N 117.9 . . ? C2 N2 C6 123.2(5) . . ? C2 N2 H2N 118.4 . . ? C6 N2 H2N 118.4 . . ? C15 N3 C13 121.8(4) . . ? C15 N3 H3N 119.1 . . ? C13 N3 H3N 119.1 . . ? C18 N4 C14 118.9(5) . . ? C18 N4 H4N 120.6 . . ? C14 N4 H4N 120.6 . . ? O1 N5 O2 121.2(5) . . ? O1 N5 O3 120.2(5) . . ? O2 N5 O3 118.6(5) . . ? O4 N6 O5 122.5(5) . . ? O4 N6 O6 119.5(5) . . ? O5 N6 O6 118.0(5) . . ? N1 C1 C2 121.4(5) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? N2 C2 C3 125.8(6) . . ? N2 C2 C1 119.3(5) . . ? C3 C2 C1 114.9(6) . . ? C4 C3 C2 121.0(6) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 121.9(6) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? N1 C5 C4 116.7(6) . . ? N1 C5 H5 121.7 . . ? C4 C5 H5 121.7 . . ? N2 C6 C7 114.5(5) . . ? N2 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C12 C7 C8 117.5(5) . . ? C12 C7 C6 121.7(5) . . ? C8 C7 C6 120.6(5) . . ? C7 C8 C9 121.6(5) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 119.1(5) . . ? C10 C9 C13 120.0(5) . . ? C8 C9 C13 120.8(5) . . ? C9 C10 C11 119.8(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.5(5) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 122.3(5) . . ? C11 C12 H12 118.8 . . ? C7 C12 H12 118.8 . . ? N3 C13 C9 113.4(4) . . ? N3 C13 H13A 108.9 . . ? C9 C13 H13A 108.9 . . ? N3 C13 H13B 108.9 . . ? C9 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 N4 117.9(5) . . ? C15 C14 H14 121.1 . . ? N4 C14 H14 121.1 . . ? N3 C15 C14 122.4(5) . . ? N3 C15 C16 119.7(5) . . ? C14 C15 C16 117.9(5) . . ? C17 C16 C15 121.3(5) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C18 C17 C16 123.9(5) . . ? C18 C17 H17 118.1 . . ? C16 C17 H17 118.1 . . ? C17 C18 N4 120.1(5) . . ? C17 C18 H18 119.9 . . ? N4 C18 H18 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.6(8) . . . . ? C6 N2 C2 C3 -4.8(8) . . . . ? C6 N2 C2 C1 176.0(4) . . . . ? N1 C1 C2 N2 177.1(5) . . . . ? N1 C1 C2 C3 -2.2(7) . . . . ? N2 C2 C3 C4 -176.6(5) . . . . ? C1 C2 C3 C4 2.6(8) . . . . ? C2 C3 C4 C5 -1.5(10) . . . . ? C1 N1 C5 C4 0.7(9) . . . . ? C3 C4 C5 N1 -0.3(10) . . . . ? C2 N2 C6 C7 -80.5(6) . . . . ? N2 C6 C7 C12 -55.9(7) . . . . ? N2 C6 C7 C8 128.5(5) . . . . ? C12 C7 C8 C9 0.4(8) . . . . ? C6 C7 C8 C9 176.3(5) . . . . ? C7 C8 C9 C10 0.7(8) . . . . ? C7 C8 C9 C13 -175.8(5) . . . . ? C8 C9 C10 C11 -1.0(8) . . . . ? C13 C9 C10 C11 175.5(5) . . . . ? C9 C10 C11 C12 0.1(8) . . . . ? C10 C11 C12 C7 1.1(8) . . . . ? C8 C7 C12 C11 -1.4(8) . . . . ? C6 C7 C12 C11 -177.1(5) . . . . ? C15 N3 C13 C9 171.4(4) . . . . ? C10 C9 C13 N3 126.1(5) . . . . ? C8 C9 C13 N3 -57.5(7) . . . . ? C18 N4 C14 C15 -1.3(7) . . . . ? C13 N3 C15 C14 -8.8(7) . . . . ? C13 N3 C15 C16 172.9(4) . . . . ? N4 C14 C15 N3 -176.0(4) . . . . ? N4 C14 C15 C16 2.4(7) . . . . ? N3 C15 C16 C17 177.0(4) . . . . ? C14 C15 C16 C17 -1.4(7) . . . . ? C15 C16 C17 C18 -0.8(8) . . . . ? C16 C17 C18 N4 2.0(8) . . . . ? C14 N4 C18 C17 -0.8(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O5 0.86 2.13 2.960(6) 161.8 . N1 H1N O6 0.86 2.19 2.884(6) 137.1 . N2 H2N O3 0.86 2.30 3.023(6) 141.9 3_666 N3 H3N O1 0.86 2.20 3.026(6) 160.1 4_575 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.181 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.042 #===END data_complex5 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(Cl O4)' _chemical_formula_sum 'C18 H20 Cl2 N4 O8' _chemical_formula_weight 491.28 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.6350(11) _cell_length_b 11.689(2) _cell_length_c 15.962(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.04(3) _cell_angle_gamma 90.00 _cell_volume 1043.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3617 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9043 _exptl_absorpt_correction_T_max 0.9269 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8027 _diffrn_reflns_av_R_equivalents 0.0870 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1842 _reflns_number_gt 1075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+4.0359P] 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 1842 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1729 _refine_ls_R_factor_gt 0.0833 _refine_ls_wR_factor_ref 0.2303 _refine_ls_wR_factor_gt 0.1671 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Cl1 Cl 0.9231(4) 0.65890(17) 0.33572(12) 0.0594(6) Uani 1 1 d . . . O1 O 0.6887(13) 0.6767(7) 0.3041(6) 0.157(4) Uani 1 1 d . . . O2 O 0.9245(16) 0.5932(7) 0.4117(4) 0.130(3) Uani 1 1 d . . . O3 O 1.0472(12) 0.7633(5) 0.3572(4) 0.095(2) Uani 1 1 d . . . O4 O 1.0453(13) 0.5922(6) 0.2809(4) 0.109(2) Uani 1 1 d . . . N1 N 0.4039(11) 0.4225(5) 0.3438(3) 0.0504(15) Uani 1 1 d . . . H1N H 0.3031 0.4682 0.3163 0.060 Uiso 1 1 calc R . . N2 N 0.5844(11) 0.4018(5) 0.2226(3) 0.0508(16) Uani 1 1 d . . . H2N H 0.6976 0.3734 0.1975 0.061 Uiso 1 1 calc R . . C1 C 0.3826(15) 0.3988(7) 0.4273(5) 0.061(2) Uani 1 1 d . . . H1 H 0.2609 0.4325 0.4532 0.073 Uiso 1 1 calc R . . C2 C 0.5361(15) 0.3278(7) 0.4708(5) 0.063(2) Uani 1 1 d . . . H2 H 0.5211 0.3111 0.5269 0.076 Uiso 1 1 calc R . . C3 C 0.7193(16) 0.2789(7) 0.4317(5) 0.068(2) Uani 1 1 d . . . H3 H 0.8282 0.2303 0.4624 0.082 Uiso 1 1 calc R . . C4 C 0.7415(15) 0.3012(6) 0.3487(5) 0.063(2) Uani 1 1 d . . . H4 H 0.8625 0.2675 0.3225 0.076 Uiso 1 1 calc R . . C5 C 0.5784(13) 0.3758(6) 0.3044(4) 0.0482(18) Uani 1 1 d . . . C6 C 0.4122(14) 0.4744(6) 0.1748(4) 0.0534(19) Uani 1 1 d . . . H6A H 0.4168 0.5496 0.2006 0.064 Uiso 1 1 calc R . . H6B H 0.2534 0.4431 0.1763 0.064 Uiso 1 1 calc R . . C7 C 0.4592(13) 0.4859(6) 0.0840(4) 0.0500(18) Uani 1 1 d . . . C8 C 0.2990(14) 0.4456(7) 0.0191(4) 0.059(2) Uani 1 1 d . . . H8 H 0.1622 0.4078 0.0314 0.071 Uiso 1 1 calc R . . C9 C 0.3368(14) 0.4602(7) -0.0644(4) 0.058(2) Uani 1 1 d . . . H9 H 0.2241 0.4335 -0.1074 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0563(12) 0.0620(12) 0.0621(12) -0.0039(11) 0.0161(9) 0.0053(11) O1 0.085(5) 0.118(6) 0.249(10) -0.056(7) -0.054(6) 0.038(5) O2 0.181(8) 0.126(6) 0.092(5) 0.023(5) 0.052(5) -0.017(6) O3 0.111(5) 0.083(4) 0.095(5) -0.015(4) 0.027(4) -0.034(4) O4 0.121(6) 0.103(5) 0.113(5) -0.019(4) 0.055(5) 0.030(4) N1 0.056(4) 0.052(4) 0.044(3) 0.006(3) 0.008(3) 0.005(3) N2 0.058(4) 0.054(4) 0.043(3) 0.000(3) 0.014(3) 0.000(3) C1 0.071(6) 0.062(5) 0.053(5) 0.002(4) 0.021(4) 0.002(5) C2 0.085(6) 0.061(5) 0.045(4) 0.004(4) 0.011(4) 0.009(5) C3 0.084(6) 0.060(5) 0.060(5) 0.011(4) 0.002(5) 0.008(5) C4 0.070(6) 0.061(5) 0.059(5) 0.003(4) 0.005(4) 0.010(4) C5 0.054(4) 0.051(4) 0.040(4) -0.002(3) 0.008(3) 0.001(4) C6 0.067(5) 0.058(5) 0.035(4) 0.003(3) 0.008(4) 0.006(4) C7 0.056(5) 0.047(4) 0.048(4) 0.003(3) 0.011(4) 0.003(4) C8 0.051(5) 0.074(5) 0.055(5) 0.005(4) 0.013(4) -0.006(4) C9 0.057(5) 0.080(6) 0.036(4) -0.007(4) -0.001(4) -0.014(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 Cl1 O1 1.371(7) . ? Cl1 O4 1.413(6) . ? Cl1 O3 1.428(6) . ? Cl1 O2 1.435(7) . ? N1 C5 1.346(8) . ? N1 C1 1.381(8) . ? N1 H1N 0.8600 . ? N2 C5 1.345(8) . ? N2 C6 1.436(9) . ? N2 H2N 0.8600 . ? C1 C2 1.330(10) . ? C1 H1 0.9300 . ? C2 C3 1.393(11) . ? C2 H2 0.9300 . ? C3 C4 1.372(10) . ? C3 H3 0.9300 . ? C4 C5 1.394(10) . ? C4 H4 0.9300 . ? C6 C7 1.511(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.371(10) . ? C7 C9 1.380(10) 3_665 ? C8 C9 1.386(9) . ? C8 H8 0.9300 . ? C9 C7 1.380(10) 3_665 ? C9 H9 0.9300 . ? 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 O1 Cl1 O4 112.1(5) . . ? O1 Cl1 O3 112.3(5) . . ? O4 Cl1 O3 111.0(4) . . ? O1 Cl1 O2 107.3(6) . . ? O4 Cl1 O2 106.0(5) . . ? O3 Cl1 O2 107.6(4) . . ? C5 N1 C1 121.6(6) . . ? C5 N1 H1N 119.2 . . ? C1 N1 H1N 119.2 . . ? C5 N2 C6 123.6(6) . . ? C5 N2 H2N 118.2 . . ? C6 N2 H2N 118.2 . . ? C2 C1 N1 120.1(7) . . ? C2 C1 H1 120.0 . . ? N1 C1 H1 120.0 . . ? C1 C2 C3 119.5(7) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 121.0(8) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.5(8) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N2 C5 N1 117.9(6) . . ? N2 C5 C4 122.7(7) . . ? N1 C5 C4 119.4(7) . . ? N2 C6 C7 112.1(6) . . ? N2 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N2 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C9 118.4(6) . 3_665 ? C8 C7 C6 121.2(7) . . ? C9 C7 C6 120.5(7) 3_665 . ? C7 C8 C9 121.3(7) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C7 C9 C8 120.3(7) 3_665 . ? C7 C9 H9 119.8 3_665 . ? C8 C9 H9 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.3(11) . . . . ? N1 C1 C2 C3 0.7(12) . . . . ? C1 C2 C3 C4 -1.1(13) . . . . ? C2 C3 C4 C5 1.0(12) . . . . ? C6 N2 C5 N1 -1.4(10) . . . . ? C6 N2 C5 C4 177.2(7) . . . . ? C1 N1 C5 N2 178.9(6) . . . . ? C1 N1 C5 C4 0.3(10) . . . . ? C3 C4 C5 N2 -179.2(7) . . . . ? C3 C4 C5 N1 -0.6(11) . . . . ? C5 N2 C6 C7 -178.4(6) . . . . ? N2 C6 C7 C8 115.7(8) . . . . ? N2 C6 C7 C9 -65.8(9) . . . 3_665 ? C9 C7 C8 C9 -1.2(13) 3_665 . . . ? C6 C7 C8 C9 177.3(7) . . . . ? C7 C8 C9 C7 1.2(13) . . . 3_665 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.86 2.08 2.921(9) 165.2 1_455 N2 H2N O3 0.86 2.19 3.033(9) 166.7 2_745 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.852 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.094 #===END data_complex6 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(Cl O4)' _chemical_formula_sum 'C18 H20 Cl2 N4 O8' _chemical_formula_weight 491.28 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.9429(10) _cell_length_b 15.579(3) _cell_length_c 13.581(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.78(3) _cell_angle_gamma 90.00 _cell_volume 1045.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5399 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9140 _exptl_absorpt_correction_T_max 0.9304 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7990 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1829 _reflns_number_gt 1283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.9762P] 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 1829 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 Cl1 Cl -0.19353(19) 0.12389(6) 0.35288(7) 0.0532(4) Uani 1 1 d . . . O1 O -0.0988(7) 0.20183(19) 0.3976(2) 0.0794(10) Uani 1 1 d . . . O2 O -0.4811(6) 0.1200(2) 0.3542(3) 0.0805(10) Uani 1 1 d . . . O3 O -0.1084(7) 0.1211(2) 0.2537(2) 0.0791(10) Uani 1 1 d . . . O4 O -0.0789(6) 0.05309(19) 0.4063(3) 0.0758(9) Uani 1 1 d . . . N1 N 0.2845(8) 0.2779(3) 0.2131(3) 0.0781(12) Uani 1 1 d . . . H1N H 0.2005 0.2379 0.2434 0.094 Uiso 1 1 calc R . . N2 N 0.8099(7) 0.4376(2) 0.2607(3) 0.0587(9) Uani 1 1 d . . . H2N H 0.8930 0.4749 0.2260 0.070 Uiso 1 1 calc R . . C1 C 0.2233(10) 0.2930(4) 0.1156(4) 0.0816(16) Uani 1 1 d . . . H1A H 0.0914 0.2608 0.0822 0.098 Uiso 1 1 calc R . . C2 C 0.3581(9) 0.3555(3) 0.0691(3) 0.0630(12) Uani 1 1 d . . . H2A H 0.3192 0.3660 0.0027 0.076 Uiso 1 1 calc R . . C3 C 0.5447(9) 0.4025(3) 0.1160(3) 0.0645(12) Uani 1 1 d . . . H3A H 0.6328 0.4453 0.0817 0.077 Uiso 1 1 calc R . . C4 C 0.6132(7) 0.3898(2) 0.2154(3) 0.0484(9) Uani 1 1 d . . . C5 C 0.4759(8) 0.3249(2) 0.2628(3) 0.0532(10) Uani 1 1 d . . . H5A H 0.5150 0.3135 0.3290 0.064 Uiso 1 1 calc R . . C6 C 0.8879(8) 0.4297(3) 0.3639(3) 0.0566(10) Uani 1 1 d . . . H6A H 1.0590 0.4591 0.3754 0.068 Uiso 1 1 calc R . . H6B H 0.9163 0.3695 0.3790 0.068 Uiso 1 1 calc R . . C7 C 0.6840(7) 0.4655(2) 0.4334(3) 0.0482(9) Uani 1 1 d . . . C8 C 0.5728(8) 0.5465(3) 0.4190(3) 0.0555(10) Uani 1 1 d . . . H8A H 0.6195 0.5786 0.3643 0.067 Uiso 1 1 calc R . . C9 C 0.3931(8) 0.5802(3) 0.4851(3) 0.0550(10) Uani 1 1 d . . . H9A H 0.3230 0.6349 0.4743 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0514(6) 0.0512(6) 0.0568(6) -0.0002(4) 0.0010(4) 0.0025(4) O1 0.099(2) 0.0539(18) 0.084(2) -0.0117(16) -0.0207(19) -0.0011(17) O2 0.0448(17) 0.103(3) 0.094(2) -0.0025(19) 0.0017(16) 0.0067(16) O3 0.082(2) 0.102(3) 0.0537(18) -0.0052(17) 0.0132(16) -0.0030(18) O4 0.075(2) 0.0579(18) 0.095(2) 0.0192(16) 0.0015(17) 0.0147(16) N1 0.067(2) 0.065(2) 0.103(3) -0.009(2) 0.010(2) -0.0118(19) N2 0.064(2) 0.053(2) 0.059(2) -0.0042(16) 0.0071(17) -0.0135(17) C1 0.068(3) 0.093(4) 0.082(4) -0.034(3) -0.025(3) 0.007(3) C2 0.064(3) 0.077(3) 0.047(2) -0.008(2) -0.011(2) 0.009(2) C3 0.073(3) 0.065(3) 0.056(3) 0.004(2) 0.004(2) 0.003(2) C4 0.046(2) 0.045(2) 0.054(2) -0.0062(17) 0.0042(17) 0.0068(17) C5 0.051(2) 0.048(2) 0.061(2) 0.0019(18) 0.0012(18) -0.0041(18) C6 0.050(2) 0.057(2) 0.063(2) -0.010(2) -0.0023(18) -0.0030(19) C7 0.045(2) 0.047(2) 0.052(2) -0.0042(17) -0.0052(17) -0.0055(17) C8 0.061(2) 0.051(2) 0.054(2) 0.0084(18) 0.000(2) -0.0040(19) C9 0.058(2) 0.044(2) 0.063(2) -0.0004(19) 0.002(2) 0.0052(18) _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 Cl1 O2 1.423(3) . ? Cl1 O3 1.424(3) . ? Cl1 O4 1.428(3) . ? Cl1 O1 1.430(3) . ? N1 C5 1.359(5) . ? N1 C1 1.369(6) . ? N1 H1N 0.8600 . ? N2 C4 1.357(5) . ? N2 C6 1.447(5) . ? N2 H2N 0.8600 . ? C1 C2 1.349(7) . ? C1 H1A 0.9300 . ? C2 C3 1.325(6) . ? C2 H2A 0.9300 . ? C3 C4 1.394(6) . ? C3 H3A 0.9300 . ? C4 C5 1.388(5) . ? C5 H5A 0.9300 . ? C6 C7 1.510(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.380(6) 3_666 ? C7 C8 1.387(5) . ? C8 C9 1.385(6) . ? C8 H8A 0.9300 . ? C9 C7 1.380(6) 3_666 ? C9 H9A 0.9300 . ? 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 O2 Cl1 O3 109.6(2) . . ? O2 Cl1 O4 110.0(2) . . ? O3 Cl1 O4 109.4(2) . . ? O2 Cl1 O1 110.2(2) . . ? O3 Cl1 O1 109.0(2) . . ? O4 Cl1 O1 108.7(2) . . ? C5 N1 C1 121.2(4) . . ? C5 N1 H1N 119.4 . . ? C1 N1 H1N 119.4 . . ? C4 N2 C6 123.9(3) . . ? C4 N2 H2N 118.0 . . ? C6 N2 H2N 118.0 . . ? C2 C1 N1 118.6(4) . . ? C2 C1 H1A 120.7 . . ? N1 C1 H1A 120.7 . . ? C3 C2 C1 121.3(4) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 122.1(4) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? N2 C4 C5 122.9(4) . . ? N2 C4 C3 120.7(4) . . ? C5 C4 C3 116.4(4) . . ? N1 C5 C4 120.3(4) . . ? N1 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? N2 C6 C7 114.3(3) . . ? N2 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C9 C7 C8 117.7(4) 3_666 . ? C9 C7 C6 121.1(4) 3_666 . ? C8 C7 C6 121.2(4) . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C7 C9 C8 121.4(4) 3_666 . ? C7 C9 H9A 119.3 3_666 . ? C8 C9 H9A 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.4(7) . . . . ? N1 C1 C2 C3 -0.6(7) . . . . ? C1 C2 C3 C4 0.3(7) . . . . ? C6 N2 C4 C5 -3.4(6) . . . . ? C6 N2 C4 C3 178.5(4) . . . . ? C2 C3 C4 N2 178.4(4) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C1 N1 C5 C4 0.2(6) . . . . ? N2 C4 C5 N1 -178.7(4) . . . . ? C3 C4 C5 N1 -0.5(6) . . . . ? C4 N2 C6 C7 -72.7(5) . . . . ? N2 C6 C7 C9 133.4(4) . . . 3_666 ? N2 C6 C7 C8 -48.3(5) . . . . ? C9 C7 C8 C9 0.7(6) 3_666 . . . ? C6 C7 C8 C9 -177.7(4) . . . . ? C7 C8 C9 C7 -0.8(6) . . . 3_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.86 2.38 3.179(5) 154.3 . N2 H2N O4 0.86 2.38 3.214(5) 164.1 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.354 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.072 #===END data_complex7 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(Cl O4)' _chemical_formula_sum 'C18 H20 Cl2 N4 O8' _chemical_formula_weight 491.28 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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' '-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 14.917(3) _cell_length_b 9.4759(19) _cell_length_c 16.141(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.52(3) _cell_angle_gamma 90.00 _cell_volume 2122.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3149 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9152 _exptl_absorpt_correction_T_max 0.9412 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7196 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_sigmaI/netI 0.0744 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1819 _reflns_number_gt 1682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1819 _refine_ls_number_parameters 183 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.1280 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.026 _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 Cl1 Cl 0.39113(7) 0.81963(11) 0.39802(7) 0.0786(4) Uani 0.840(7) 1 d PD A 1 O1 O 0.3653(4) 0.7078(4) 0.3319(3) 0.148(2) Uani 0.840(7) 1 d PD A 1 O2 O 0.3176(4) 0.8518(6) 0.4273(4) 0.167(3) Uani 0.840(7) 1 d PD A 1 O3 O 0.4726(3) 0.7719(6) 0.4696(3) 0.136(2) Uani 0.840(7) 1 d PD A 1 O4 O 0.4157(5) 0.9378(5) 0.3571(4) 0.152(3) Uani 0.840(7) 1 d PD A 1 Cl1' Cl 0.39113(7) 0.81963(11) 0.39802(7) 0.0786(4) Uani 0.160(7) 1 d PD A 2 O1' O 0.2875(6) 0.823(2) 0.3554(14) 0.113(8) Uani 0.160(7) 1 d PDU A 2 O2' O 0.418(2) 0.907(2) 0.4769(11) 0.191(14) Uani 0.160(7) 1 d PDU A 2 O3' O 0.4247(14) 0.6801(12) 0.4225(15) 0.105(8) Uani 0.160(7) 1 d PDU A 2 O4' O 0.4288(13) 0.885(2) 0.3374(11) 0.064(6) Uani 0.160(7) 1 d PDU A 2 N1 N 0.7500(2) 0.6615(3) 0.37578(18) 0.0745(9) Uani 1 1 d . . . H1N H 0.7552 0.5711 0.3784 0.089 Uiso 1 1 calc R . . N2 N 0.6118(2) 0.6428(3) 0.40897(19) 0.0752(9) Uani 1 1 d . . . H2N H 0.5675 0.6884 0.4198 0.090 Uiso 1 1 calc R . . C1 C 0.6766(3) 0.7203(4) 0.3895(2) 0.0625(9) Uani 1 1 d . . . C2 C 0.6689(3) 0.8715(4) 0.3840(2) 0.0764(11) Uani 1 1 d . . . H2 H 0.6188 0.9172 0.3945 0.092 Uiso 1 1 calc R . . C3 C 0.7340(3) 0.9457(4) 0.3638(2) 0.0789(11) Uani 1 1 d . . . H3 H 0.7292 1.0435 0.3592 0.095 Uiso 1 1 calc R . . C4 C 0.8096(3) 0.8755(5) 0.3494(3) 0.0905(13) Uani 1 1 d . . . H4 H 0.8547 0.9260 0.3341 0.109 Uiso 1 1 calc R . . C5 C 0.8164(3) 0.7366(5) 0.3579(3) 0.0890(13) Uani 1 1 d . . . H5 H 0.8684 0.6905 0.3513 0.107 Uiso 1 1 calc R . . C6 C 0.6085(3) 0.4897(3) 0.4137(2) 0.0709(10) Uani 1 1 d . . . H6A H 0.5803 0.4646 0.4572 0.085 Uiso 1 1 calc R . . H6B H 0.6741 0.4543 0.4355 0.085 Uiso 1 1 calc R . . C7 C 0.5000 0.4864(5) 0.2500 0.0597(12) Uani 1 2 d S . . H7 H 0.5000 0.5845 0.2500 0.072 Uiso 1 2 calc SR . . C8 C 0.5527(2) 0.4151(4) 0.3274(2) 0.0594(9) Uani 1 1 d . . . C9 C 0.5522(3) 0.2680(4) 0.3262(2) 0.0709(10) Uani 1 1 d . . . H9 H 0.5877 0.2184 0.3775 0.085 Uiso 1 1 calc R . . C10 C 0.5000 0.1957(6) 0.2500 0.0794(15) Uani 1 2 d S . . H10 H 0.5000 0.0975 0.2500 0.095 Uiso 1 2 calc SR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0635(6) 0.0734(7) 0.1001(8) 0.0122(6) 0.0314(6) 0.0125(5) O1 0.189(5) 0.095(3) 0.147(4) -0.025(3) 0.047(4) -0.006(3) O2 0.107(4) 0.224(5) 0.208(6) 0.022(5) 0.102(4) 0.061(4) O3 0.103(3) 0.211(5) 0.096(3) 0.037(3) 0.039(3) 0.067(3) O4 0.227(6) 0.090(3) 0.162(5) 0.015(3) 0.096(4) -0.008(4) Cl1' 0.0635(6) 0.0734(7) 0.1001(8) 0.0122(6) 0.0314(6) 0.0125(5) O1' 0.100(11) 0.126(12) 0.120(12) 0.010(9) 0.047(8) -0.004(8) O2' 0.197(17) 0.185(16) 0.183(16) 0.001(10) 0.061(10) 0.005(10) O3' 0.107(11) 0.098(10) 0.107(12) 0.021(8) 0.037(8) -0.006(8) O4' 0.063(8) 0.073(10) 0.076(9) 0.016(7) 0.048(7) -0.001(7) N1 0.064(2) 0.080(2) 0.080(2) -0.0002(16) 0.0268(17) 0.0119(17) N2 0.0578(19) 0.077(2) 0.093(2) -0.0108(16) 0.0308(16) 0.0073(16) C1 0.057(2) 0.073(2) 0.051(2) -0.0058(18) 0.0121(17) -0.011(2) C2 0.054(2) 0.086(3) 0.085(3) -0.003(2) 0.021(2) 0.010(2) C3 0.072(3) 0.071(3) 0.090(3) 0.007(2) 0.026(2) -0.005(2) C4 0.070(3) 0.103(4) 0.099(3) 0.010(3) 0.032(2) -0.013(3) C5 0.068(3) 0.098(3) 0.111(4) 0.004(3) 0.044(3) 0.005(2) C6 0.065(2) 0.066(2) 0.084(3) -0.002(2) 0.0293(19) -0.0009(19) C7 0.048(3) 0.055(3) 0.075(3) 0.000 0.023(3) 0.000 C8 0.0463(19) 0.069(2) 0.071(2) 0.0030(19) 0.0312(17) -0.0014(17) C9 0.079(3) 0.068(2) 0.076(3) 0.007(2) 0.040(2) 0.0051(19) C10 0.092(4) 0.064(3) 0.093(4) 0.000 0.046(4) 0.000 _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 Cl1 O2 1.377(4) . ? Cl1 O3 1.409(4) . ? Cl1 O4 1.415(4) . ? Cl1 O1 1.452(4) . ? N1 C1 1.317(4) . ? N1 C5 1.335(5) . ? N1 H1N 0.8600 . ? N2 C1 1.339(4) . ? N2 C6 1.455(4) . ? N2 H2N 0.8600 . ? C1 C2 1.438(5) . ? C2 C3 1.333(5) . ? C2 H2 0.9300 . ? C3 C4 1.401(5) . ? C3 H3 0.9300 . ? C4 C5 1.323(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.511(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.383(4) 2_655 ? C7 C8 1.383(4) . ? C7 H7 0.9300 . ? C8 C9 1.394(5) . ? C9 C10 1.373(4) . ? C9 H9 0.9300 . ? C10 C9 1.373(4) 2_655 ? C10 H10 0.9300 . ? 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 O2 Cl1 O3 110.2(3) . . ? O2 Cl1 O4 111.1(4) . . ? O3 Cl1 O4 110.1(4) . . ? O2 Cl1 O1 112.6(4) . . ? O3 Cl1 O1 106.6(3) . . ? O4 Cl1 O1 106.2(3) . . ? C1 N1 C5 122.7(4) . . ? C1 N1 H1N 118.7 . . ? C5 N1 H1N 118.7 . . ? C1 N2 C6 126.9(3) . . ? C1 N2 H2N 116.5 . . ? C6 N2 H2N 116.5 . . ? N1 C1 N2 121.5(3) . . ? N1 C1 C2 117.6(4) . . ? N2 C1 C2 120.9(4) . . ? C3 C2 C1 119.4(4) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.6(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.4(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 N1 121.2(4) . . ? C4 C5 H5 119.4 . . ? N1 C5 H5 119.4 . . ? N2 C6 C8 115.8(3) . . ? N2 C6 H6A 108.3 . . ? C8 C6 H6A 108.3 . . ? N2 C6 H6B 108.3 . . ? C8 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C8 C7 C8 121.6(5) 2_655 . ? C8 C7 H7 119.2 2_655 . ? C8 C7 H7 119.2 . . ? C7 C8 C9 118.5(4) . . ? C7 C8 C6 122.9(3) . . ? C9 C8 C6 118.6(3) . . ? C10 C9 C8 120.6(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C9 120.1(5) . 2_655 ? C9 C10 H10 119.9 . . ? C9 C10 H10 119.9 2_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 N2 -178.7(3) . . . . ? C5 N1 C1 C2 0.5(5) . . . . ? C6 N2 C1 N1 -3.1(5) . . . . ? C6 N2 C1 C2 177.7(3) . . . . ? N1 C1 C2 C3 1.3(5) . . . . ? N2 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? C2 C3 C4 C5 -1.3(6) . . . . ? C3 C4 C5 N1 3.2(6) . . . . ? C1 N1 C5 C4 -2.8(6) . . . . ? C1 N2 C6 C8 -88.3(4) . . . . ? C8 C7 C8 C9 0.3(2) 2_655 . . . ? C8 C7 C8 C6 -178.1(3) 2_655 . . . ? N2 C6 C8 C7 -6.0(4) . . . . ? N2 C6 C8 C9 175.7(3) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C6 C8 C9 C10 177.9(3) . . . . ? C8 C9 C10 C9 0.3(2) . . . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.86 2.30 3.116(6) 159.6 3_545 N2 H2N O3 0.86 2.03 2.875(5) 167.8 . N2 H2N Cl1 0.86 2.81 3.641(3) 161.9 . _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.147 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.035 #===END data_complex8 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 827158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4, 2(Cl O4)' _chemical_formula_sum 'C18 H20 Cl2 N4 O8' _chemical_formula_weight 491.28 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.0052(10) _cell_length_b 20.411(4) _cell_length_c 20.976(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.02(3) _cell_angle_gamma 90.00 _cell_volume 2137.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3499 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9002 _exptl_absorpt_correction_T_max 0.9318 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15486 _diffrn_reflns_av_R_equivalents 0.0899 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3556 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3556 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2324 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Cl1 Cl 1.1351(4) 0.52748(10) 0.37138(9) 0.0876(6) Uani 1 1 d . . . Cl2 Cl 1.2222(4) 0.63136(8) 0.00708(9) 0.0784(6) Uani 1 1 d . . . O1 O 1.0551(10) 0.5908(2) 0.3521(2) 0.1326(19) Uani 1 1 d . . . O2 O 1.4182(10) 0.5224(2) 0.3755(2) 0.1212(17) Uani 1 1 d . . . O3 O 1.0295(9) 0.4804(2) 0.3252(2) 0.1071(16) Uani 1 1 d . . . O4 O 1.0354(9) 0.5117(2) 0.4323(2) 0.1117(16) Uani 1 1 d . . . O5 O 1.1078(9) 0.6733(2) -0.0404(2) 0.1090(16) Uani 1 1 d . . . O6 O 1.1812(9) 0.65750(18) 0.0676(2) 0.1051(15) Uani 1 1 d . . . O7 O 1.0978(8) 0.56800(18) 0.0027(2) 0.1025(15) Uani 1 1 d . . . O8 O 1.4995(8) 0.62401(19) -0.0016(2) 0.1030(15) Uani 1 1 d . . . N1 N 0.7683(16) 0.5596(6) 0.1205(8) 0.167(7) Uani 1 1 d . . . H1N H 0.8757 0.5759 0.0944 0.201 Uiso 1 1 calc R . . N2 N 0.2557(18) 0.4349(4) 0.1358(3) 0.157(3) Uani 1 1 d . . . H2N H 0.1951 0.4281 0.0970 0.189 Uiso 1 1 calc R . . N3 N 0.7664(11) 0.3632(3) 0.3891(3) 0.0976(19) Uani 1 1 d . . . H3N H 0.8298 0.4023 0.3870 0.117 Uiso 1 1 calc R . . N4 N 0.2939(12) 0.2800(3) 0.4865(3) 0.121(2) Uani 1 1 d . . . H4N H 0.2244 0.2419 0.4910 0.145 Uiso 1 1 calc R . . C1 C 0.621(3) 0.5129(9) 0.1017(5) 0.168(9) Uani 1 1 d . . . H1 H 0.6206 0.4978 0.0599 0.201 Uiso 1 1 calc R . . C2 C 0.457(4) 0.4839(5) 0.1446(9) 0.140(9) Uani 1 1 d . . . C3 C 0.4536(15) 0.5068(6) 0.1986(7) 0.119(4) Uani 1 1 d . . . H3 H 0.3426 0.4882 0.2274 0.143 Uiso 1 1 calc R . . C4 C 0.606(3) 0.5578(8) 0.2168(5) 0.169(7) Uani 1 1 d . . . H4 H 0.5985 0.5745 0.2579 0.202 Uiso 1 1 calc R . . C5 C 0.767(4) 0.5849(6) 0.1775(9) 0.203(9) Uani 1 1 d . . . H5 H 0.8756 0.6203 0.1899 0.243 Uiso 1 1 calc R . . C6 C 0.1371(12) 0.3941(3) 0.1848(3) 0.091(2) Uani 1 1 d . . . H6A H -0.0239 0.3731 0.1663 0.109 Uiso 1 1 calc R . . H6B H 0.0874 0.4218 0.2197 0.109 Uiso 1 1 calc R . . C7 C 0.3298(14) 0.3432(3) 0.2100(4) 0.0761(19) Uani 1 1 d . . . C8 C 0.4913(14) 0.3525(3) 0.2650(4) 0.0785(19) Uani 1 1 d . . . H8 H 0.4781 0.3914 0.2876 0.094 Uiso 1 1 calc R . . C9 C 0.6684(16) 0.3066(4) 0.2871(4) 0.087(2) Uani 1 1 d . . . C10 C 0.6992(17) 0.2511(4) 0.2524(4) 0.114(3) Uani 1 1 d . . . H10 H 0.8268 0.2204 0.2669 0.137 Uiso 1 1 calc R . . C11 C 0.547(2) 0.2394(4) 0.1967(5) 0.158(4) Uani 1 1 d . . . H11 H 0.5637 0.2003 0.1746 0.190 Uiso 1 1 calc R . . C12 C 0.3667(16) 0.2869(4) 0.1742(3) 0.111(2) Uani 1 1 d . . . H12 H 0.2702 0.2812 0.1350 0.133 Uiso 1 1 calc R . . C13 C 0.8564(13) 0.3169(4) 0.3458(4) 0.103(3) Uani 1 1 d . . . H13A H 0.8828 0.2754 0.3677 0.124 Uiso 1 1 calc R . . H13B H 1.0288 0.3310 0.3323 0.124 Uiso 1 1 calc R . . C14 C 0.4743(12) 0.2906(3) 0.4399(3) 0.082(2) Uani 1 1 d . . . H14 H 0.5184 0.2568 0.4129 0.099 Uiso 1 1 calc R . . C15 C 0.5865(13) 0.3518(3) 0.4345(4) 0.0767(19) Uani 1 1 d . . . C16 C 0.5114(16) 0.3980(3) 0.4766(4) 0.105(3) Uani 1 1 d . . . H16 H 0.5848 0.4397 0.4745 0.126 Uiso 1 1 calc R . . C17 C 0.3418(16) 0.3866(3) 0.5197(3) 0.081(2) Uani 1 1 d . . . H17 H 0.3018 0.4202 0.5474 0.098 Uiso 1 1 calc R . . C18 C 0.2279(14) 0.3307(5) 0.5252(3) 0.100(2) Uani 1 1 d . . . H18 H 0.1019 0.3247 0.5553 0.119 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0926(15) 0.0959(14) 0.0758(15) -0.0072(11) 0.0174(12) -0.0156(12) Cl2 0.0733(13) 0.0694(11) 0.0920(16) -0.0033(11) 0.0031(11) -0.0008(10) O1 0.176(5) 0.088(3) 0.134(5) 0.012(3) 0.011(4) -0.012(4) O2 0.096(4) 0.152(4) 0.120(4) -0.011(3) 0.035(3) -0.011(3) O3 0.126(4) 0.113(3) 0.086(4) -0.028(3) 0.031(3) -0.033(3) O4 0.130(4) 0.139(4) 0.068(3) -0.004(3) 0.021(3) -0.011(3) O5 0.107(4) 0.123(4) 0.095(4) 0.025(3) -0.006(3) 0.023(3) O6 0.154(4) 0.091(3) 0.071(3) -0.017(3) 0.014(3) -0.016(3) O7 0.094(3) 0.074(3) 0.142(4) -0.033(3) 0.026(3) -0.014(3) O8 0.070(3) 0.109(3) 0.129(4) 0.011(3) 0.003(3) 0.000(3) N1 0.074(5) 0.193(12) 0.237(15) 0.133(11) 0.034(7) -0.012(5) N2 0.205(9) 0.178(7) 0.083(6) -0.021(6) -0.031(6) 0.099(7) N3 0.091(4) 0.115(5) 0.086(5) 0.027(4) -0.002(4) -0.038(4) N4 0.102(5) 0.106(5) 0.152(6) 0.019(5) -0.010(5) -0.005(4) C1 0.241(17) 0.205(15) 0.067(7) 0.050(9) 0.080(11) 0.157(14) C2 0.180(19) 0.081(10) 0.142(17) -0.025(12) -0.117(16) 0.015(11) C3 0.067(5) 0.097(7) 0.194(14) 0.044(7) 0.012(7) -0.023(5) C4 0.268(17) 0.170(12) 0.073(8) 0.031(8) 0.051(10) 0.059(12) C5 0.28(2) 0.143(9) 0.165(15) 0.001(11) -0.138(15) -0.023(11) C6 0.076(5) 0.135(6) 0.059(5) 0.023(4) -0.006(4) 0.027(5) C7 0.072(5) 0.071(4) 0.085(6) -0.004(4) 0.006(4) -0.004(4) C8 0.069(5) 0.091(5) 0.076(6) 0.001(4) 0.008(4) -0.002(4) C9 0.096(6) 0.106(6) 0.060(6) 0.012(5) 0.009(5) 0.010(5) C10 0.154(8) 0.093(6) 0.095(7) 0.019(5) 0.004(6) 0.036(6) C11 0.250(12) 0.099(6) 0.119(9) -0.031(6) -0.030(8) 0.073(7) C12 0.132(7) 0.102(6) 0.094(6) -0.017(5) -0.021(5) 0.009(5) C13 0.091(6) 0.138(6) 0.086(6) 0.026(5) 0.040(5) 0.026(5) C14 0.070(4) 0.082(5) 0.097(6) 0.005(4) 0.026(4) -0.003(4) C15 0.074(5) 0.066(4) 0.084(6) 0.016(4) -0.034(4) -0.015(4) C16 0.143(7) 0.071(5) 0.097(6) 0.003(5) -0.023(6) -0.042(5) C17 0.132(6) 0.053(4) 0.061(5) -0.004(3) 0.018(5) -0.005(4) C18 0.099(6) 0.121(7) 0.082(6) -0.010(5) 0.025(5) 0.017(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 Cl1 O1 1.404(5) . ? Cl1 O2 1.417(5) . ? Cl1 O3 1.439(4) . ? Cl1 O4 1.441(4) . ? Cl2 O5 1.404(4) . ? Cl2 O6 1.406(4) . ? Cl2 O8 1.421(4) . ? Cl2 O7 1.436(4) . ? N1 C1 1.254(16) . ? N1 C5 1.303(13) . ? N1 H1N 0.8600 . ? N2 C2 1.421(15) . ? N2 C6 1.479(8) . ? N2 H2N 0.8600 . ? N3 C15 1.375(7) . ? N3 C13 1.407(7) . ? N3 H3N 0.8600 . ? N4 C18 1.370(7) . ? N4 C14 1.393(7) . ? N4 H4N 0.8600 . ? C1 C2 1.391(18) . ? C1 H1 0.9300 . ? C2 C3 1.228(13) . ? C3 C4 1.330(13) . ? C3 H3 0.9300 . ? C4 C5 1.315(17) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.489(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.374(8) . ? C7 C12 1.393(8) . ? C8 C9 1.349(8) . ? C8 H8 0.9300 . ? C9 C10 1.360(8) . ? C9 C13 1.511(9) . ? C10 C11 1.371(9) . ? C10 H10 0.9300 . ? C11 C12 1.384(9) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.379(7) . ? C14 H14 0.9300 . ? C15 C16 1.362(8) . ? C16 C17 1.303(8) . ? C16 H16 0.9300 . ? C17 C18 1.285(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? 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 O1 Cl1 O2 110.4(3) . . ? O1 Cl1 O3 109.7(3) . . ? O2 Cl1 O3 108.1(3) . . ? O1 Cl1 O4 110.6(3) . . ? O2 Cl1 O4 109.7(3) . . ? O3 Cl1 O4 108.3(3) . . ? O5 Cl2 O6 109.4(3) . . ? O5 Cl2 O8 109.1(3) . . ? O6 Cl2 O8 111.2(3) . . ? O5 Cl2 O7 110.5(3) . . ? O6 Cl2 O7 108.1(3) . . ? O8 Cl2 O7 108.7(3) . . ? C1 N1 C5 123.4(13) . . ? C1 N1 H1N 118.3 . . ? C5 N1 H1N 118.3 . . ? C2 N2 C6 128.4(11) . . ? C2 N2 H2N 115.8 . . ? C6 N2 H2N 115.8 . . ? C15 N3 C13 126.1(6) . . ? C15 N3 H3N 117.0 . . ? C13 N3 H3N 117.0 . . ? C18 N4 C14 119.6(6) . . ? C18 N4 H4N 120.2 . . ? C14 N4 H4N 120.2 . . ? N1 C1 C2 118.8(12) . . ? N1 C1 H1 120.6 . . ? C2 C1 H1 120.6 . . ? C3 C2 C1 118.8(12) . . ? C3 C2 N2 109(2) . . ? C1 C2 N2 131.3(18) . . ? C2 C3 C4 121.2(12) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.0(13) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? N1 C5 C4 116.7(14) . . ? N1 C5 H5 121.6 . . ? C4 C5 H5 121.6 . . ? N2 C6 C7 111.0(5) . . ? N2 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N2 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C12 118.3(7) . . ? C8 C7 C6 122.0(7) . . ? C12 C7 C6 119.5(8) . . ? C9 C8 C7 121.8(7) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 119.4(8) . . ? C8 C9 C13 122.7(8) . . ? C10 C9 C13 117.6(8) . . ? C9 C10 C11 121.6(8) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C12 118.6(8) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C11 C12 C7 120.1(8) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? N3 C13 C9 114.3(6) . . ? N3 C13 H13A 108.7 . . ? C9 C13 H13A 108.7 . . ? N3 C13 H13B 108.7 . . ? C9 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 N4 119.1(7) . . ? C15 C14 H14 120.5 . . ? N4 C14 H14 120.5 . . ? C16 C15 N3 123.8(7) . . ? C16 C15 C14 116.1(7) . . ? N3 C15 C14 120.1(7) . . ? C17 C16 C15 123.3(7) . . ? C17 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C18 C17 C16 122.4(7) . . ? C18 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C17 C18 N4 119.3(6) . . ? C17 C18 H18 120.3 . . ? N4 C18 H18 120.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -3(2) . . . . ? N1 C1 C2 C3 3.0(18) . . . . ? N1 C1 C2 N2 173.9(12) . . . . ? C6 N2 C2 C3 -25.7(14) . . . . ? C6 N2 C2 C1 162.7(10) . . . . ? C1 C2 C3 C4 -0.9(18) . . . . ? N2 C2 C3 C4 -173.7(8) . . . . ? C2 C3 C4 C5 -0.7(19) . . . . ? C1 N1 C5 C4 2(2) . . . . ? C3 C4 C5 N1 0(2) . . . . ? C2 N2 C6 C7 -73.2(12) . . . . ? N2 C6 C7 C8 95.4(8) . . . . ? N2 C6 C7 C12 -78.6(8) . . . . ? C12 C7 C8 C9 -4.9(10) . . . . ? C6 C7 C8 C9 -178.9(6) . . . . ? C7 C8 C9 C10 3.6(10) . . . . ? C7 C8 C9 C13 177.3(6) . . . . ? C8 C9 C10 C11 -2.7(12) . . . . ? C13 C9 C10 C11 -176.6(8) . . . . ? C9 C10 C11 C12 3.1(14) . . . . ? C10 C11 C12 C7 -4.4(13) . . . . ? C8 C7 C12 C11 5.3(11) . . . . ? C6 C7 C12 C11 179.5(7) . . . . ? C15 N3 C13 C9 82.0(8) . . . . ? C8 C9 C13 N3 24.5(9) . . . . ? C10 C9 C13 N3 -161.7(6) . . . . ? C18 N4 C14 C15 1.1(9) . . . . ? C13 N3 C15 C16 178.1(7) . . . . ? C13 N3 C15 C14 -0.8(10) . . . . ? N4 C14 C15 C16 0.6(9) . . . . ? N4 C14 C15 N3 179.5(5) . . . . ? N3 C15 C16 C17 -179.6(6) . . . . ? C14 C15 C16 C17 -0.7(11) . . . . ? C15 C16 C17 C18 -1.1(13) . . . . ? C16 C17 C18 N4 2.8(12) . . . . ? C14 N4 C18 C17 -2.8(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O7 0.86 2.29 3.071(13) 150.2 . N1 H1N O6 0.86 2.36 3.133(9) 150.4 . N2 H2N O7 0.86 2.47 3.294(8) 161.0 3_665 N3 H3N O3 0.86 2.33 3.082(6) 147.0 . N4 H4N O5 0.86 2.46 3.222(7) 148.4 2_645 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.442 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.048