# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Guoping Yong' _publ_contact_author_email GPYONG@USTC.EDU.CN _publ_section_title ; New zwitterionic radical and its perchlorate salts: dimers in solution and one-dimensional stacking chains with unusual properties in solid state ; loop_ _publ_author_name 'Guoping Yong' 'Chong-Fu Li' 'Ying-Zhou Li' 'Shi-Wei Luo' #TrackingRef 'Compd1.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 737813' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Cl N4 O5' _chemical_formula_weight 350.72 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.0120(14) _cell_length_b 20.713(4) _cell_length_c 9.7170(19) _cell_angle_alpha 90.00 _cell_angle_beta 93.40(3) _cell_angle_gamma 90.00 _cell_volume 1408.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1590 _cell_measurement_theta_min 2.8732 _cell_measurement_theta_max 28.9974 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.906 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Gemini S Ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7124 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.1207 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2751 _reflns_number_gt 1287 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2751 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _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 0.88859(11) 0.15343(4) 0.72055(9) 0.0474(2) Uani 1 1 d . . . O5 O 0.9241(3) 0.18675(12) 0.8475(2) 0.0869(8) Uani 1 1 d . . . N3 N 0.5801(3) 0.07382(10) 0.1572(2) 0.0313(6) Uani 1 1 d . . . O1 O 0.7589(2) 0.01261(9) 0.4745(2) 0.0461(6) Uani 1 1 d . . . N2 N 1.0314(3) 0.09803(11) 0.3755(2) 0.0375(6) Uani 1 1 d . . . C13 C 0.4340(4) 0.03404(13) 0.1969(3) 0.0343(7) Uani 1 1 d . . . O3 O 0.9001(3) 0.19707(10) 0.6082(2) 0.0655(7) Uani 1 1 d . . . C14 C 0.6737(4) 0.02870(13) 0.3620(3) 0.0359(7) Uani 1 1 d . . . N4 N 0.4916(3) 0.00709(11) 0.3179(2) 0.0398(6) Uani 1 1 d . . . O2 O 0.7002(3) 0.12704(11) 0.7158(3) 0.0852(9) Uani 1 1 d . . . N1 N 1.1449(3) 0.17472(11) 0.2516(3) 0.0353(6) Uani 1 1 d . . . C3 C 1.4765(4) 0.19180(16) 0.4080(4) 0.0525(9) Uani 1 1 d . . . H3C H 1.5912 0.1979 0.4594 0.063 Uiso 1 1 calc R . . C1 C 1.1803(4) 0.13851(13) 0.3669(3) 0.0355(7) Uani 1 1 d . . . O4 O 1.0222(3) 0.10257(12) 0.7065(3) 0.0894(9) Uani 1 1 d . . . C7 C 0.8998(4) 0.10790(13) 0.2656(3) 0.0320(7) Uani 1 1 d . . . C6 C 0.9700(4) 0.15618(13) 0.1881(3) 0.0384(7) Uani 1 1 d . . . H6A H 0.9120 0.1735 0.1079 0.046 Uiso 1 1 calc R . . C12 C 0.2660(4) 0.02789(14) 0.1166(3) 0.0406(8) Uani 1 1 d . . . H12A H 0.1686 0.0010 0.1435 0.049 Uiso 1 1 calc R . . C5 C 1.2737(4) 0.21963(14) 0.2106(4) 0.0499(9) Uani 1 1 d . . . H5B H 1.2487 0.2438 0.1310 0.060 Uiso 1 1 calc R . . C9 C 0.5601(4) 0.10674(13) 0.0360(3) 0.0415(8) Uani 1 1 d . . . H9A H 0.6589 0.1327 0.0079 0.050 Uiso 1 1 calc R . . C11 C 0.2464(4) 0.06216(14) -0.0032(3) 0.0457(8) Uani 1 1 d . . . H11A H 0.1335 0.0593 -0.0581 0.055 Uiso 1 1 calc R . . C8 C 0.7307(4) 0.07012(13) 0.2583(3) 0.0311(7) Uani 1 1 d . . . C4 C 1.4375(4) 0.22786(15) 0.2888(4) 0.0540(10) Uani 1 1 d . . . H4B H 1.5260 0.2582 0.2624 0.065 Uiso 1 1 calc R . . C10 C 0.3943(4) 0.10145(14) -0.0439(3) 0.0468(8) Uani 1 1 d . . . H10A H 0.3797 0.1243 -0.1264 0.056 Uiso 1 1 calc R . . C2 C 1.3475(4) 0.14742(15) 0.4502(3) 0.0464(8) Uani 1 1 d . . . H2A H 1.3703 0.1241 0.5313 0.056 Uiso 1 1 calc R . . H1 H 1.014(3) 0.0690(12) 0.443(3) 0.043(9) Uiso 1 1 d . . . H2 H 0.412(4) -0.0156(13) 0.366(3) 0.056(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0529(5) 0.0488(5) 0.0407(5) 0.0038(5) 0.0061(4) 0.0002(5) O5 0.127(2) 0.0912(19) 0.0418(17) -0.0184(15) 0.0039(15) -0.0139(16) N3 0.0299(13) 0.0319(14) 0.0324(16) 0.0022(13) 0.0046(11) -0.0003(12) O1 0.0405(12) 0.0639(15) 0.0335(13) 0.0150(12) -0.0016(10) -0.0052(10) N2 0.0372(14) 0.0415(14) 0.0340(16) 0.0065(13) 0.0044(12) -0.0056(13) C13 0.0402(18) 0.0328(17) 0.030(2) -0.0034(15) 0.0054(15) 0.0026(15) O3 0.0861(16) 0.0580(14) 0.0513(16) 0.0176(13) -0.0049(12) -0.0165(12) C14 0.0308(17) 0.0398(19) 0.038(2) -0.0025(17) 0.0056(15) -0.0023(15) N4 0.0387(15) 0.0411(15) 0.0396(17) 0.0116(14) 0.0030(12) -0.0092(13) O2 0.0659(16) 0.0890(18) 0.104(2) -0.0022(16) 0.0300(15) -0.0285(14) N1 0.0293(14) 0.0316(14) 0.0453(17) 0.0036(13) 0.0059(12) -0.0005(13) C3 0.0359(19) 0.052(2) 0.069(3) -0.018(2) -0.0018(18) -0.0039(18) C1 0.0376(18) 0.0305(18) 0.039(2) -0.0043(16) 0.0061(15) -0.0007(16) O4 0.0969(18) 0.1012(19) 0.068(2) -0.0003(17) -0.0085(15) 0.0614(17) C7 0.0343(17) 0.0318(17) 0.0303(18) 0.0007(15) 0.0049(14) 0.0023(15) C6 0.0349(17) 0.0393(18) 0.0405(19) 0.0069(17) -0.0006(14) -0.0008(16) C12 0.0371(18) 0.0410(19) 0.044(2) -0.0030(17) 0.0032(15) -0.0011(15) C5 0.043(2) 0.038(2) 0.070(3) 0.0112(19) 0.0099(19) -0.0035(17) C9 0.0446(19) 0.0432(19) 0.037(2) 0.0061(18) 0.0063(15) -0.0020(16) C11 0.0398(19) 0.051(2) 0.045(2) -0.0084(18) -0.0079(16) 0.0019(17) C8 0.0294(16) 0.0361(17) 0.0278(17) 0.0054(15) 0.0027(13) -0.0009(15) C4 0.043(2) 0.042(2) 0.078(3) -0.006(2) 0.013(2) -0.0087(18) C10 0.054(2) 0.049(2) 0.037(2) 0.0046(18) -0.0045(17) 0.0042(18) C2 0.0448(19) 0.053(2) 0.041(2) -0.0048(18) -0.0012(16) 0.0060(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 O4 1.422(2) . ? Cl1 O5 1.423(2) . ? Cl1 O3 1.423(2) . ? Cl1 O2 1.428(2) . ? N3 C9 1.361(3) . ? N3 C13 1.388(3) . ? N3 C8 1.400(3) . ? O1 C14 1.259(3) . ? N2 C1 1.345(3) . ? N2 C7 1.384(3) . ? N2 H2B 0.8600 . ? C13 N4 1.342(3) . ? C13 C12 1.380(4) . ? C14 C8 1.400(4) . ? C14 N4 1.396(3) . ? N4 H4A 0.8600 . ? N1 C1 1.359(3) . ? N1 C5 1.372(3) . ? N1 C6 1.394(3) . ? C3 C2 1.370(4) . ? C3 C4 1.392(4) . ? C3 H3C 0.9300 . ? C1 C2 1.397(4) . ? C7 C6 1.361(3) . ? C7 C8 1.419(3) . ? C6 H6A 0.9300 . ? C12 C11 1.363(4) . ? C12 H12A 0.9300 . ? C5 C4 1.350(4) . ? C5 H5B 0.9300 . ? C9 C10 1.364(4) . ? C9 H9A 0.9300 . ? C11 C10 1.394(4) . ? C11 H11A 0.9300 . ? C4 H4B 0.9300 . ? C10 H10A 0.9300 . ? C2 H2A 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 O4 Cl1 O5 111.12(16) . . ? O4 Cl1 O3 109.22(15) . . ? O5 Cl1 O3 110.02(14) . . ? O4 Cl1 O2 109.07(15) . . ? O5 Cl1 O2 109.12(15) . . ? O3 Cl1 O2 108.23(14) . . ? C9 N3 C13 119.9(2) . . ? C9 N3 C8 132.0(2) . . ? C13 N3 C8 108.1(2) . . ? C1 N2 C7 110.2(2) . . ? C1 N2 H2B 124.9 . . ? C7 N2 H2B 124.9 . . ? N4 C13 C12 131.3(3) . . ? N4 C13 N3 107.6(2) . . ? C12 C13 N3 121.2(3) . . ? O1 C14 C8 130.3(3) . . ? O1 C14 N4 124.0(2) . . ? C8 C14 N4 105.7(2) . . ? C13 N4 C14 111.0(2) . . ? C13 N4 H4A 124.5 . . ? C14 N4 H4A 124.5 . . ? C1 N1 C5 121.5(3) . . ? C1 N1 C6 109.0(2) . . ? C5 N1 C6 129.4(3) . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3C 119.7 . . ? C4 C3 H3C 119.7 . . ? N2 C1 N1 106.9(3) . . ? N2 C1 C2 132.4(3) . . ? N1 C1 C2 120.7(3) . . ? C6 C7 N2 106.8(2) . . ? C6 C7 C8 134.9(3) . . ? N2 C7 C8 118.3(2) . . ? C7 C6 N1 107.1(2) . . ? C7 C6 H6A 126.4 . . ? N1 C6 H6A 126.4 . . ? C11 C12 C13 118.3(3) . . ? C11 C12 H12A 120.8 . . ? C13 C12 H12A 120.8 . . ? C4 C5 N1 118.4(3) . . ? C4 C5 H5B 120.8 . . ? N1 C5 H5B 120.8 . . ? C10 C9 N3 119.6(3) . . ? C10 C9 H9A 120.2 . . ? N3 C9 H9A 120.2 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C14 C8 N3 107.6(2) . . ? C14 C8 C7 125.1(3) . . ? N3 C8 C7 126.7(3) . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4B 119.4 . . ? C3 C4 H4B 119.4 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C3 C2 C1 117.5(3) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? 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 C9 N3 C13 N4 179.1(2) . . . . ? C8 N3 C13 N4 0.3(3) . . . . ? C9 N3 C13 C12 -1.1(4) . . . . ? C8 N3 C13 C12 -179.9(2) . . . . ? C12 C13 N4 C14 -178.9(3) . . . . ? N3 C13 N4 C14 0.9(3) . . . . ? O1 C14 N4 C13 177.6(3) . . . . ? C8 C14 N4 C13 -1.6(3) . . . . ? C7 N2 C1 N1 0.1(3) . . . . ? C7 N2 C1 C2 -179.7(3) . . . . ? C5 N1 C1 N2 -177.8(2) . . . . ? C6 N1 C1 N2 0.2(3) . . . . ? C5 N1 C1 C2 2.0(4) . . . . ? C6 N1 C1 C2 -180.0(2) . . . . ? C1 N2 C7 C6 -0.4(3) . . . . ? C1 N2 C7 C8 -179.0(2) . . . . ? N2 C7 C6 N1 0.5(3) . . . . ? C8 C7 C6 N1 178.7(3) . . . . ? C1 N1 C6 C7 -0.4(3) . . . . ? C5 N1 C6 C7 177.3(2) . . . . ? N4 C13 C12 C11 179.5(3) . . . . ? N3 C13 C12 C11 -0.2(4) . . . . ? C1 N1 C5 C4 -0.7(4) . . . . ? C6 N1 C5 C4 -178.2(3) . . . . ? C13 N3 C9 C10 1.5(4) . . . . ? C8 N3 C9 C10 -180.0(3) . . . . ? C13 C12 C11 C10 1.1(4) . . . . ? O1 C14 C8 N3 -177.4(3) . . . . ? N4 C14 C8 N3 1.7(3) . . . . ? O1 C14 C8 C7 -5.3(5) . . . . ? N4 C14 C8 C7 173.8(2) . . . . ? C9 N3 C8 C14 -179.9(3) . . . . ? C13 N3 C8 C14 -1.3(3) . . . . ? C9 N3 C8 C7 8.2(5) . . . . ? C13 N3 C8 C7 -173.2(2) . . . . ? C6 C7 C8 C14 -169.9(3) . . . . ? N2 C7 C8 C14 8.2(4) . . . . ? C6 C7 C8 N3 0.7(5) . . . . ? N2 C7 C8 N3 178.7(2) . . . . ? N1 C5 C4 C3 0.2(5) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? N3 C9 C10 C11 -0.7(4) . . . . ? C12 C11 C10 C9 -0.7(4) . . . . ? C4 C3 C2 C1 2.1(4) . . . . ? N2 C1 C2 C3 177.1(3) . . . . ? N1 C1 C2 C3 -2.7(4) . . . . ? 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 N2 H2B O1 0.86 2.22 2.815(3) 125.8 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.285 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.045 # Attachment 'Compd2.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 741384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl2 N4 O11' _chemical_formula_weight 487.20 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 C2/c 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 27.774(6) _cell_length_b 10.523(2) _cell_length_c 13.389(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.94(3) _cell_angle_gamma 90.00 _cell_volume 3842.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1335 _cell_measurement_theta_min 3.0972 _cell_measurement_theta_max 32.2327 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1960 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8670 _exptl_absorpt_correction_T_max 0.9031 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15053 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 32.58 _reflns_number_total 6291 _reflns_number_gt 3028 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6291 _refine_ls_number_parameters 283 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1498 _refine_ls_R_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.3191 _refine_ls_wR_factor_gt 0.2887 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.028 _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 0.00480(4) 0.22247(10) 0.46564(7) 0.0533(3) Uani 1 1 d . . . O4 O 0.00158(16) 0.1483(5) 0.5538(3) 0.0961(13) Uani 1 1 d . . . O3 O -0.0267(2) 0.1723(5) 0.3821(4) 0.133(2) Uani 1 1 d . . . O5 O 0.05497(19) 0.2150(5) 0.4576(5) 0.137(2) Uani 1 1 d . . . Cl2 Cl 0.18665(4) 0.11961(10) 0.38001(9) 0.0628(4) Uani 1 1 d D . . N3 N 0.10475(11) -0.4215(3) 0.4027(2) 0.0410(6) Uani 1 1 d . . . C8 C 0.12944(13) -0.3843(3) 0.4984(2) 0.0403(7) Uani 1 1 d . . . N2 N 0.17583(12) -0.4105(3) 0.6703(2) 0.0444(7) Uani 1 1 d . . . N1 N 0.18001(11) -0.6162(3) 0.6897(2) 0.0449(7) Uani 1 1 d . . . O1 O 0.14712(11) -0.1779(3) 0.5736(2) 0.0579(7) Uani 1 1 d . . . C7 C 0.15142(12) -0.4657(4) 0.5798(2) 0.0403(7) Uani 1 1 d . . . N4 N 0.10203(13) -0.2140(3) 0.4063(2) 0.0485(7) Uani 1 1 d . . . C1 C 0.19310(13) -0.5036(4) 0.7378(3) 0.0429(8) Uani 1 1 d . . . C14 C 0.12688(14) -0.2526(4) 0.4986(3) 0.0441(8) Uani 1 1 d . . . C13 C 0.08839(13) -0.3171(4) 0.3477(3) 0.0449(8) Uani 1 1 d . . . C6 C 0.15448(14) -0.5929(4) 0.5932(3) 0.0454(8) Uani 1 1 d . . . H6A H 0.1416 -0.6540 0.5453 0.054 Uiso 1 1 calc R . . C2 C 0.21972(16) -0.4996(5) 0.8376(3) 0.0575(10) Uani 1 1 d . . . H2A H 0.2290 -0.4230 0.8702 0.069 Uiso 1 1 calc R . . C9 C 0.09651(15) -0.5427(4) 0.3614(3) 0.0514(9) Uani 1 1 d . . . H9A H 0.1080 -0.6148 0.3985 0.062 Uiso 1 1 calc R . . C5 C 0.19165(16) -0.7300(4) 0.7392(3) 0.0572(10) Uani 1 1 d . . . H5A H 0.1822 -0.8062 0.7060 0.069 Uiso 1 1 calc R . . C12 C 0.06221(14) -0.3250(5) 0.2468(3) 0.0538(10) Uani 1 1 d . . . H12A H 0.0512 -0.2527 0.2095 0.065 Uiso 1 1 calc R . . C10 C 0.07041(16) -0.5511(5) 0.2627(3) 0.0584(10) Uani 1 1 d . . . H10A H 0.0639 -0.6309 0.2334 0.070 Uiso 1 1 calc R . . C3 C 0.23139(16) -0.6126(5) 0.8845(3) 0.0649(12) Uani 1 1 d . . . H3A H 0.2495 -0.6139 0.9505 0.078 Uiso 1 1 calc R . . C11 C 0.05379(15) -0.4443(5) 0.2063(3) 0.0572(11) Uani 1 1 d . . . H11A H 0.0367 -0.4536 0.1399 0.069 Uiso 1 1 calc R . . C4 C 0.21619(17) -0.7309(5) 0.8339(4) 0.0653(12) Uani 1 1 d . . . H4A H 0.2237 -0.8076 0.8678 0.078 Uiso 1 1 calc R . . O7 O 0.1679(4) 0.0029(6) 0.3365(10) 0.303(7) Uani 1 1 d DU . . O8 O 0.2350(3) 0.0797(15) 0.4220(8) 0.316(9) Uani 1 1 d DU . . O11 O 0.10715(16) 0.9692(4) 0.0930(4) 0.1010(14) Uani 1 1 d . . . O10 O 0.0578(2) -0.0066(4) 0.3004(3) 0.1052(14) Uani 1 1 d . . . O6 O 0.1666(4) 0.1649(9) 0.4553(9) 0.274(6) Uani 1 1 d DU . . O2 O -0.0083(2) 0.3477(4) 0.4795(3) 0.1068(15) Uani 1 1 d . . . H02 H 0.1012(14) -0.138(4) 0.384(3) 0.042(10) Uiso 1 1 d . . . O9 O 0.1983(4) 0.2120(8) 0.3109(7) 0.219(4) Uiso 1 1 d D . . H01 H 0.1825(17) -0.340(5) 0.688(3) 0.058(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0580(6) 0.0469(5) 0.0527(5) -0.0008(4) 0.0050(4) 0.0024(4) O4 0.101(3) 0.110(3) 0.081(2) 0.032(2) 0.027(2) 0.005(3) O3 0.185(5) 0.097(3) 0.085(3) 0.003(2) -0.056(3) -0.020(3) O5 0.088(3) 0.126(4) 0.213(6) 0.059(4) 0.068(4) 0.006(3) Cl2 0.0660(7) 0.0483(6) 0.0761(7) 0.0135(5) 0.0186(5) 0.0043(5) N3 0.0390(15) 0.0455(16) 0.0385(13) 0.0013(12) 0.0074(11) 0.0008(13) C8 0.0435(18) 0.0433(18) 0.0335(15) 0.0000(13) 0.0055(13) 0.0013(14) N2 0.0534(19) 0.0399(17) 0.0380(14) 0.0005(13) 0.0039(12) -0.0024(14) N1 0.0435(16) 0.0415(16) 0.0502(16) 0.0095(13) 0.0104(13) 0.0048(13) O1 0.0645(18) 0.0477(16) 0.0552(15) -0.0022(12) -0.0049(13) 0.0098(13) C7 0.0388(17) 0.0445(18) 0.0375(15) 0.0050(13) 0.0066(12) 0.0027(14) N4 0.0518(19) 0.0453(18) 0.0449(16) 0.0073(14) 0.0003(13) 0.0079(15) C1 0.0404(18) 0.0443(19) 0.0437(17) 0.0069(15) 0.0071(13) 0.0026(15) C14 0.050(2) 0.0445(19) 0.0374(15) 0.0023(14) 0.0057(14) 0.0068(16) C13 0.0406(18) 0.055(2) 0.0391(16) 0.0054(15) 0.0085(13) 0.0048(16) C6 0.050(2) 0.0420(19) 0.0422(17) 0.0000(14) 0.0050(14) -0.0013(15) C2 0.053(2) 0.069(3) 0.0483(19) 0.0085(19) 0.0035(16) 0.000(2) C9 0.057(2) 0.048(2) 0.0481(19) 0.0005(16) 0.0074(16) -0.0060(17) C5 0.058(2) 0.049(2) 0.064(2) 0.0169(19) 0.0102(19) 0.0076(19) C12 0.046(2) 0.073(3) 0.0402(18) 0.0106(18) 0.0038(15) 0.0052(19) C10 0.057(2) 0.067(3) 0.049(2) -0.0124(19) 0.0061(17) -0.017(2) C3 0.049(2) 0.093(4) 0.050(2) 0.024(2) 0.0020(17) 0.010(2) C11 0.049(2) 0.083(3) 0.0379(17) -0.0048(19) 0.0034(15) -0.008(2) C4 0.058(3) 0.071(3) 0.067(3) 0.030(2) 0.012(2) 0.016(2) O7 0.339(14) 0.061(4) 0.51(2) -0.038(7) 0.081(14) -0.025(6) O8 0.122(7) 0.58(3) 0.252(11) 0.117(14) 0.039(7) 0.091(11) O11 0.092(3) 0.057(2) 0.149(4) 0.007(2) 0.011(3) -0.020(2) O10 0.136(4) 0.070(3) 0.104(3) 0.024(2) 0.011(3) 0.020(3) O6 0.348(13) 0.192(7) 0.363(14) -0.014(8) 0.274(12) 0.051(8) O2 0.156(4) 0.053(2) 0.099(3) -0.004(2) -0.007(3) 0.027(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 Cl1 O3 1.387(4) . ? Cl1 O2 1.389(4) . ? Cl1 O5 1.420(5) . ? Cl1 O4 1.433(4) . ? Cl2 O6 1.329(6) . ? Cl2 O7 1.416(6) . ? Cl2 O8 1.418(6) . ? Cl2 O9 1.421(7) . ? N3 C13 1.352(5) . ? N3 C8 1.391(4) . ? N3 C9 1.392(5) . ? C8 C14 1.388(5) . ? C8 C7 1.429(5) . ? N2 C1 1.357(5) . ? N2 C7 1.398(5) . ? N1 C1 1.365(5) . ? N1 C6 1.373(5) . ? N1 C5 1.377(5) . ? O1 C14 1.315(5) . ? C7 C6 1.351(5) . ? N4 C13 1.350(5) . ? N4 C14 1.358(5) . ? C1 C2 1.400(5) . ? C13 C12 1.410(5) . ? C2 C3 1.355(7) . ? C9 C10 1.385(6) . ? C5 C4 1.320(7) . ? C12 C11 1.370(6) . ? C10 C11 1.383(7) . ? C3 C4 1.442(8) . ? 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 O3 Cl1 O2 109.1(3) . . ? O3 Cl1 O5 113.3(4) . . ? O2 Cl1 O5 110.4(3) . . ? O3 Cl1 O4 109.2(3) . . ? O2 Cl1 O4 110.3(3) . . ? O5 Cl1 O4 104.4(3) . . ? O6 Cl2 O7 116.6(7) . . ? O6 Cl2 O8 107.9(7) . . ? O7 Cl2 O8 98.8(7) . . ? O6 Cl2 O9 115.3(6) . . ? O7 Cl2 O9 115.9(6) . . ? O8 Cl2 O9 98.3(6) . . ? C13 N3 C8 109.2(3) . . ? C13 N3 C9 121.1(3) . . ? C8 N3 C9 129.7(3) . . ? C14 C8 N3 105.4(3) . . ? C14 C8 C7 127.8(3) . . ? N3 C8 C7 126.8(3) . . ? C1 N2 C7 109.3(3) . . ? C1 N1 C6 109.4(3) . . ? C1 N1 C5 120.7(3) . . ? C6 N1 C5 129.9(3) . . ? C6 C7 N2 106.8(3) . . ? C6 C7 C8 134.6(3) . . ? N2 C7 C8 118.6(3) . . ? C13 N4 C14 109.0(3) . . ? N2 C1 N1 106.5(3) . . ? N2 C1 C2 132.1(4) . . ? N1 C1 C2 121.5(4) . . ? O1 C14 N4 125.9(3) . . ? O1 C14 C8 125.7(3) . . ? N4 C14 C8 108.4(3) . . ? N4 C13 N3 108.0(3) . . ? N4 C13 C12 129.9(4) . . ? N3 C13 C12 122.1(4) . . ? C7 C6 N1 108.1(3) . . ? C3 C2 C1 116.9(4) . . ? C10 C9 N3 117.0(4) . . ? C4 C5 N1 120.0(4) . . ? C11 C12 C13 116.9(4) . . ? C11 C10 C9 122.0(4) . . ? C2 C3 C4 121.1(4) . . ? C12 C11 C10 120.9(4) . . ? C5 C4 C3 119.8(4) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.835 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.124