# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Chris Orvig' _publ_contact_author_email ORVIG@CHEM.UBC.CA _publ_section_title ; Altering pyridinone N-substituents to optimise activity as potential prodrugs for Alzheimer's disease ; loop_ _publ_author_name 'Chris Orvig' 'Brent D G Page' 'Brian O Patrick' 'Lauren E Scott' # Attachment 'Cu_nbp_2.cif' data_co340 _database_code_depnum_ccdc_archive 'CCDC 697416' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Cu(nbp)2 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Cl6 Cu N2 O4' _chemical_formula_weight 730.75 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' Cu Cu 0.3201 1.2651 '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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.3840(3) _cell_length_b 21.0223(12) _cell_length_c 11.7249(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.787(2) _cell_angle_gamma 90.00 _cell_volume 1562.53(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4397 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 25.17 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 742 _exptl_absorpt_coefficient_mu 1.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_T_max 0.883 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13415 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3545 _reflns_number_gt 2533 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0419P)^2^+2.3856P] 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 3545 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.008 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4803(8) -0.1418(2) 0.7068(4) 0.0851(15) Uani 1 1 d . . . H1A H 0.5629 -0.1662 0.6565 0.128 Uiso 1 1 calc R . . H1B H 0.3307 -0.1528 0.6895 0.128 Uiso 1 1 calc R . . H1C H 0.5283 -0.1521 0.7871 0.128 Uiso 1 1 calc R . . C2 C 0.5088(7) -0.0733(2) 0.6874(3) 0.0646(11) Uani 1 1 d . A . C3 C 0.3482(6) -0.03758(19) 0.6273(3) 0.0527(9) Uani 1 1 d . . . C4 C 0.3766(7) 0.02759(18) 0.6074(3) 0.0541(9) Uani 1 1 d . . . C5 C 0.5746(7) 0.0558(2) 0.6503(3) 0.0648(11) Uani 1 1 d . . . H5 H 0.6003 0.0998 0.6396 0.078 Uiso 1 1 calc R . . C6 C 0.7235(8) 0.0180(3) 0.7066(3) 0.0751(13) Uani 1 1 d . A . H6 H 0.8558 0.0365 0.7339 0.090 Uiso 1 1 calc R . . C7 C 0.856(5) -0.0836(14) 0.789(3) 0.061(4) Uani 0.50 1 d P A 1 H7A H 0.9963 -0.0641 0.7844 0.073 Uiso 0.50 1 calc PR A 1 H7B H 0.8555 -0.1259 0.7518 0.073 Uiso 0.50 1 calc PR A 1 C7B C 0.894(6) -0.0687(17) 0.791(3) 0.107(11) Uani 0.50 1 d P A 2 H7B1 H 1.0090 -0.0380 0.7837 0.128 Uiso 0.50 1 calc PR A 2 H7B2 H 0.9319 -0.1093 0.7559 0.128 Uiso 0.50 1 calc PR A 2 C8 C 0.827(3) -0.0922(10) 0.910(2) 0.045(4) Uani 0.50 1 d P A 1 C8B C 0.877(3) -0.0804(14) 0.923(2) 0.071(6) Uani 0.50 1 d P A 2 C9 C 0.6596(13) -0.0754(5) 0.9610(7) 0.058(2) Uani 0.50 1 d P A 1 H9 H 0.5450 -0.0552 0.9161 0.070 Uiso 0.50 1 calc PR A 1 C9B C 0.7558(18) -0.0383(6) 0.9820(8) 0.082(3) Uani 0.50 1 d P A 2 H9B H 0.6906 -0.0019 0.9454 0.098 Uiso 0.50 1 calc PR A 2 C10 C 0.6450(16) -0.0863(5) 1.0765(8) 0.065(3) Uani 0.50 1 d P A 1 H10 H 0.5174 -0.0779 1.1080 0.078 Uiso 0.50 1 calc PR A 1 C10B C 0.7356(19) -0.0526(7) 1.0956(8) 0.090(4) Uani 0.50 1 d P A 2 H10B H 0.6649 -0.0238 1.1403 0.108 Uiso 0.50 1 calc PR A 2 C11 C 0.8194(8) -0.1096(3) 1.1451(4) 0.0788(13) Uani 0.50 1 d P A 1 H11 H 0.8190 -0.1090 1.2261 0.095 Uiso 0.50 1 calc PR A 1 C11B C 0.8194(8) -0.1096(3) 1.1451(4) 0.0788(13) Uani 0.50 1 d P A 2 H11B H 0.7897 -0.1236 1.2185 0.095 Uiso 0.50 1 calc PR A 2 C12 C 1.001(4) -0.1346(14) 1.099(2) 0.065(5) Uani 0.50 1 d P A 1 H12 H 1.1045 -0.1584 1.1454 0.078 Uiso 0.50 1 calc PR A 1 C12B C 0.937(4) -0.1409(13) 1.086(3) 0.064(5) Uani 0.50 1 d P A 2 H12B H 1.0180 -0.1747 1.1222 0.077 Uiso 0.50 1 calc PR A 2 C13 C 1.020(2) -0.1230(12) 0.986(2) 0.057(4) Uani 0.50 1 d P A 1 H13 H 1.1461 -0.1333 0.9540 0.069 Uiso 0.50 1 calc PR A 1 C13B C 0.954(2) -0.1291(11) 0.9713(19) 0.049(3) Uani 0.50 1 d P A 2 H13B H 1.0251 -0.1588 0.9286 0.059 Uiso 0.50 1 calc PR A 2 C14 C 0.4454(6) 0.69923(18) 0.9826(4) 0.0680(12) Uani 1 1 d . . . H14 H 0.4433 0.6526 0.9990 0.082 Uiso 1 1 calc R . . N1 N 0.6955(5) -0.04401(19) 0.7262(2) 0.0627(9) Uani 1 1 d . . . O1 O 0.2242(4) 0.05829(11) 0.5512(2) 0.0534(6) Uani 1 1 d . . . O2 O 0.1631(4) -0.06379(11) 0.5851(2) 0.0545(6) Uani 1 1 d . . . Cu1 Cu 0.0000 0.0000 0.5000 0.04354(18) Uani 1 2 d S . . Cl1 Cl 0.6560(2) 0.71536(7) 0.90670(17) 0.1218(7) Uani 1 1 d . . . Cl2 Cl 0.4681(3) 0.74049(7) 1.11314(16) 0.1142(6) Uani 1 1 d . . . Cl3 Cl 0.2110(2) 0.71962(7) 0.89943(18) 0.1184(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.093(3) 0.073(3) 0.094(3) 0.026(3) 0.033(3) 0.028(3) C2 0.073(3) 0.078(3) 0.048(2) 0.008(2) 0.031(2) 0.014(2) C3 0.063(2) 0.065(2) 0.0342(17) 0.0076(16) 0.0257(16) 0.0175(19) C4 0.080(3) 0.053(2) 0.0330(18) -0.0048(16) 0.0243(18) 0.002(2) C5 0.081(3) 0.070(3) 0.048(2) -0.009(2) 0.024(2) -0.006(2) C6 0.075(3) 0.114(4) 0.039(2) -0.010(2) 0.020(2) -0.001(3) C7 0.053(9) 0.088(7) 0.046(7) -0.001(5) 0.024(6) 0.016(6) C7B 0.067(14) 0.21(3) 0.048(9) 0.027(17) 0.022(9) 0.047(16) C8 0.040(9) 0.057(6) 0.036(6) -0.003(4) -0.004(5) 0.000(5) C8B 0.040(10) 0.135(19) 0.039(7) -0.012(9) 0.015(7) 0.018(9) C9 0.049(4) 0.094(7) 0.034(4) -0.007(4) 0.012(3) -0.006(4) C9B 0.089(7) 0.109(9) 0.050(5) 0.006(6) 0.018(5) 0.053(7) C10 0.059(5) 0.096(8) 0.043(5) -0.010(5) 0.012(4) -0.017(5) C10B 0.087(8) 0.142(12) 0.044(5) -0.001(7) 0.026(5) 0.045(8) C11 0.095(4) 0.099(4) 0.044(2) 0.007(2) 0.014(2) 0.010(3) C11B 0.095(4) 0.099(4) 0.044(2) 0.007(2) 0.014(2) 0.010(3) C12 0.074(13) 0.075(10) 0.042(7) -0.007(6) -0.013(8) 0.014(10) C12B 0.070(12) 0.050(7) 0.066(11) 0.005(6) -0.019(8) 0.003(8) C13 0.029(7) 0.076(9) 0.063(9) -0.012(6) -0.013(7) 0.012(7) C13B 0.041(8) 0.059(7) 0.043(6) -0.019(5) -0.007(7) 0.015(8) C14 0.063(2) 0.0357(19) 0.108(4) 0.001(2) 0.023(2) 0.0018(17) N1 0.067(2) 0.090(3) 0.0350(16) 0.0057(16) 0.0219(15) 0.0169(19) O1 0.0677(16) 0.0450(14) 0.0501(14) -0.0045(11) 0.0180(12) -0.0017(12) O2 0.0655(16) 0.0462(14) 0.0568(15) 0.0125(11) 0.0283(13) 0.0070(12) Cu1 0.0614(4) 0.0352(3) 0.0377(3) 0.0016(2) 0.0210(2) 0.0018(3) Cl1 0.0983(10) 0.0823(9) 0.1995(18) 0.0390(10) 0.0788(11) 0.0135(8) Cl2 0.1317(13) 0.0700(8) 0.1427(14) -0.0419(9) 0.0237(10) -0.0075(8) Cl3 0.0820(9) 0.0708(8) 0.1951(18) -0.0131(10) -0.0144(10) 0.0205(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.474(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.370(6) . ? C2 C3 1.393(5) . ? C3 O2 1.344(5) . ? C3 C4 1.405(5) . ? C4 O1 1.283(5) . ? C4 C5 1.433(6) . ? C5 C6 1.350(6) . ? C5 H5 0.9500 . ? C6 N1 1.340(6) . ? C6 H6 0.9500 . ? C7 N1 1.45(4) . ? C7 C8 1.47(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7B N1 1.49(4) . ? C7B C8B 1.59(5) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8 C9 1.33(2) . ? C8 C13 1.57(3) . ? C8B C13B 1.24(4) . ? C8B C9B 1.41(3) . ? C9 C10 1.387(12) . ? C9 H9 0.9500 . ? C9B C10B 1.386(13) . ? C9B H9B 0.9500 . ? C10 C11 1.384(12) . ? C10 H10 0.9500 . ? C10B H10B 0.9500 . ? C11 C12 1.44(3) . ? C11 H11 0.9500 . ? C12 C13 1.37(4) . ? C12 H12 0.9500 . ? C12B C13B 1.38(4) . ? C12B H12B 0.9500 . ? C13 H13 0.9500 . ? C13B H13B 0.9500 . ? C14 Cl1 1.731(4) . ? C14 Cl3 1.740(5) . ? C14 Cl2 1.750(5) . ? C14 H14 1.0000 . ? O1 Cu1 1.925(2) . ? O2 Cu1 1.906(2) . ? Cu1 O2 1.906(2) 3_556 ? Cu1 O1 1.925(2) 3_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 119.1(4) . . ? N1 C2 C1 120.4(4) . . ? C3 C2 C1 120.5(4) . . ? O2 C3 C2 121.9(4) . . ? O2 C3 C4 117.6(3) . . ? C2 C3 C4 120.5(4) . . ? O1 C4 C3 118.1(4) . . ? O1 C4 C5 123.8(4) . . ? C3 C4 C5 118.1(4) . . ? C6 C5 C4 117.9(4) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? N1 C6 C5 123.8(5) . . ? N1 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? N1 C7 C8 114(2) . . ? N1 C7 H7A 108.8 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.8 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N1 C7B C8B 114(2) . . ? N1 C7B H7B1 108.9 . . ? C8B C7B H7B1 108.8 . . ? N1 C7B H7B2 108.8 . . ? C8B C7B H7B2 108.8 . . ? H7B1 C7B H7B2 107.7 . . ? C9 C8 C7 127(2) . . ? C9 C8 C13 118.5(19) . . ? C7 C8 C13 115(2) . . ? C13B C8B C9B 120(2) . . ? C13B C8B C7B 120(2) . . ? C9B C8B C7B 119(3) . . ? C8 C9 C10 122.8(13) . . ? C8 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C10B C9B C8B 116.9(15) . . ? C10B C9B H9B 121.5 . . ? C8B C9B H9B 121.6 . . ? C11 C10 C9 118.9(8) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C9B C10B H10B 119.8 . . ? C10 C11 C12 122.6(11) . . ? C10 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C13 C12 C11 118(2) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 120.9 . . ? C13B C12B H12B 118.0 . . ? C12 C13 C8 117.7(18) . . ? C12 C13 H13 121.1 . . ? C8 C13 H13 121.2 . . ? C8B C13B C12B 121(2) . . ? C8B C13B H13B 119.4 . . ? C12B C13B H13B 119.5 . . ? Cl1 C14 Cl3 109.4(3) . . ? Cl1 C14 Cl2 111.3(2) . . ? Cl3 C14 Cl2 110.2(2) . . ? Cl1 C14 H14 108.6 . . ? Cl3 C14 H14 108.6 . . ? Cl2 C14 H14 108.6 . . ? C6 N1 C2 120.5(4) . . ? C6 N1 C7 123.0(12) . . ? C2 N1 C7 116.5(12) . . ? C6 N1 C7B 107.7(14) . . ? C2 N1 C7B 131.8(14) . . ? C7 N1 C7B 15(2) . . ? C4 O1 Cu1 109.3(2) . . ? C3 O2 Cu1 107.8(2) . . ? O2 Cu1 O2 180.00(13) . 3_556 ? O2 Cu1 O1 93.17(11) . 3_556 ? O2 Cu1 O1 86.83(11) 3_556 3_556 ? O2 Cu1 O1 86.83(11) . . ? O2 Cu1 O1 93.17(11) 3_556 . ? O1 Cu1 O1 180.00(11) 3_556 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 178.7(3) . . . . ? C1 C2 C3 O2 0.1(5) . . . . ? N1 C2 C3 C4 -0.5(5) . . . . ? C1 C2 C3 C4 -179.0(3) . . . . ? O2 C3 C4 O1 0.6(4) . . . . ? C2 C3 C4 O1 179.7(3) . . . . ? O2 C3 C4 C5 -179.0(3) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? O1 C4 C5 C6 -178.9(3) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C4 C5 C6 N1 -1.2(5) . . . . ? N1 C7 C8 C9 10(3) . . . . ? N1 C7 C8 C13 -168.5(17) . . . . ? N1 C7B C8B C13B 137(2) . . . . ? N1 C7B C8B C9B -36(3) . . . . ? C7 C8 C9 C10 179.1(18) . . . . ? C13 C8 C9 C10 -3(2) . . . . ? C13B C8B C9B C10B 3(3) . . . . ? C7B C8B C9B C10B 176.3(18) . . . . ? C8 C9 C10 C11 6.7(18) . . . . ? C9 C10 C11 C12 -12.4(18) . . . . ? C10 C11 C12 C13 14(3) . . . . ? C11 C12 C13 C8 -9(3) . . . . ? C9 C8 C13 C12 4(3) . . . . ? C7 C8 C13 C12 -178(2) . . . . ? C9B C8B C13B C12B -5(3) . . . . ? C7B C8B C13B C12B -178(2) . . . . ? C5 C6 N1 C2 0.9(5) . . . . ? C5 C6 N1 C7 -178.7(14) . . . . ? C5 C6 N1 C7B -179.5(14) . . . . ? C3 C2 N1 C6 0.0(5) . . . . ? C1 C2 N1 C6 178.6(4) . . . . ? C3 C2 N1 C7 179.6(13) . . . . ? C1 C2 N1 C7 -1.9(14) . . . . ? C3 C2 N1 C7B -179.5(18) . . . . ? C1 C2 N1 C7B -0.9(19) . . . . ? C8 C7 N1 C6 97.7(19) . . . . ? C8 C7 N1 C2 -82(2) . . . . ? C8 C7 N1 C7B 101(10) . . . . ? C8B C7B N1 C6 105(2) . . . . ? C8B C7B N1 C2 -76(3) . . . . ? C8B C7B N1 C7 -73(9) . . . . ? C3 C4 O1 Cu1 -4.3(3) . . . . ? C5 C4 O1 Cu1 175.3(3) . . . . ? C2 C3 O2 Cu1 -175.7(2) . . . . ? C4 C3 O2 Cu1 3.5(3) . . . . ? C3 O2 Cu1 O2 71(100) . . . 3_556 ? C3 O2 Cu1 O1 175.5(2) . . . 3_556 ? C3 O2 Cu1 O1 -4.5(2) . . . . ? C4 O1 Cu1 O2 4.9(2) . . . . ? C4 O1 Cu1 O2 -175.1(2) . . . 3_556 ? C4 O1 Cu1 O1 165(59) . . . 3_556 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.685 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.063 # Attachment 'Cu_ppp_2.cif' data_co346 _database_code_depnum_ccdc_archive 'CCDC 697417' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 Cl6 Cu N2 O4' _chemical_formula_weight 702.70 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' Cu Cu 0.3201 1.2651 '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 orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5466(11) _cell_length_b 11.6975(11) _cell_length_c 20.9936(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2835.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9056 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 25.78 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1420 _exptl_absorpt_coefficient_mu 1.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.811 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35879 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2789 _reflns_number_gt 2124 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0311P)^2^+2.0545P] 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 2789 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0713 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5247(2) -0.3304(2) 0.36767(11) 0.0282(5) Uani 1 1 d . . . H1A H 0.5892 -0.3792 0.3810 0.042 Uiso 1 1 calc R . . H1B H 0.5549 -0.2572 0.3522 0.042 Uiso 1 1 calc R . . H1C H 0.4814 -0.3683 0.3335 0.042 Uiso 1 1 calc R . . C2 C 0.44606(19) -0.30971(18) 0.42309(10) 0.0191(5) Uani 1 1 d . . . C3 C 0.44848(18) -0.20740(18) 0.45587(10) 0.0173(4) Uani 1 1 d . . . C4 C 0.36780(19) -0.18679(18) 0.50613(9) 0.0177(4) Uani 1 1 d . . . C5 C 0.28706(19) -0.27152(19) 0.52074(10) 0.0222(5) Uani 1 1 d . . . H5 H 0.2310 -0.2591 0.5531 0.027 Uiso 1 1 calc R . . C6 C 0.28930(19) -0.37222(19) 0.48815(10) 0.0224(5) Uani 1 1 d . . . H6 H 0.2354 -0.4304 0.4990 0.027 Uiso 1 1 calc R . . C7 C 0.36177(19) -0.50215(18) 0.40955(10) 0.0202(5) Uani 1 1 d . . . C8 C 0.2627(2) -0.53279(19) 0.37693(10) 0.0239(5) Uani 1 1 d . . . H8 H 0.1990 -0.4815 0.3743 0.029 Uiso 1 1 calc R . . C9 C 0.2572(2) -0.6392(2) 0.34811(11) 0.0281(5) Uani 1 1 d . . . H9 H 0.1890 -0.6615 0.3261 0.034 Uiso 1 1 calc R . . C10 C 0.3500(2) -0.7128(2) 0.35127(11) 0.0312(6) Uani 1 1 d . . . H10 H 0.3463 -0.7850 0.3307 0.037 Uiso 1 1 calc R . . C11 C 0.4491(2) -0.6817(2) 0.38448(11) 0.0318(6) Uani 1 1 d . . . H11 H 0.5129 -0.7329 0.3871 0.038 Uiso 1 1 calc R . . C12 C 0.4546(2) -0.5758(2) 0.41383(11) 0.0276(5) Uani 1 1 d . . . H12 H 0.5220 -0.5540 0.4368 0.033 Uiso 1 1 calc R . . C13 C 0.3642(2) -0.4808(2) 0.17875(11) 0.0280(5) Uani 1 1 d . . . H13 H 0.3911 -0.4684 0.1340 0.034 Uiso 1 1 calc R . . N1 N 0.36618(15) -0.39140(15) 0.44078(8) 0.0195(4) Uani 1 1 d . . . O1 O 0.37522(13) -0.08870(12) 0.53573(7) 0.0207(3) Uani 1 1 d . . . O2 O 0.52212(13) -0.12431(12) 0.44231(6) 0.0212(3) Uani 1 1 d . . . Cu1 Cu 0.5000 0.0000 0.5000 0.01713(10) Uani 1 2 d S . . Cl1 Cl 0.31719(7) -0.34929(6) 0.20984(4) 0.0500(2) Uani 1 1 d . . . Cl2 Cl 0.24888(6) -0.57789(6) 0.17769(3) 0.04101(17) Uani 1 1 d . . . Cl3 Cl 0.48086(6) -0.53228(7) 0.22375(3) 0.04567(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0323(14) 0.0250(12) 0.0272(11) -0.0073(10) 0.0098(10) -0.0065(10) C2 0.0191(11) 0.0186(11) 0.0197(10) -0.0007(8) -0.0002(9) -0.0003(9) C3 0.0159(11) 0.0178(10) 0.0181(10) 0.0012(8) -0.0017(9) -0.0006(9) C4 0.0198(11) 0.0178(11) 0.0154(10) -0.0002(8) -0.0035(9) 0.0007(9) C5 0.0194(11) 0.0241(12) 0.0230(11) -0.0004(9) 0.0050(9) 0.0004(9) C6 0.0200(12) 0.0215(12) 0.0257(11) 0.0010(9) 0.0011(10) -0.0042(9) C7 0.0250(12) 0.0165(10) 0.0192(10) 0.0006(9) 0.0005(9) -0.0026(10) C8 0.0261(13) 0.0210(11) 0.0244(11) 0.0021(9) -0.0016(10) -0.0032(10) C9 0.0328(14) 0.0275(13) 0.0240(11) -0.0020(10) -0.0038(11) -0.0107(11) C10 0.0529(17) 0.0175(12) 0.0232(12) -0.0029(9) 0.0006(12) -0.0055(11) C11 0.0412(16) 0.0239(12) 0.0304(13) -0.0007(10) -0.0041(12) 0.0093(11) C12 0.0290(13) 0.0258(12) 0.0280(12) -0.0014(10) -0.0070(11) 0.0014(10) C13 0.0338(14) 0.0290(13) 0.0210(11) 0.0014(9) 0.0005(10) 0.0004(11) N1 0.0194(10) 0.0168(9) 0.0223(9) -0.0021(7) -0.0003(8) -0.0016(8) O1 0.0238(8) 0.0178(8) 0.0206(7) -0.0034(6) 0.0041(6) -0.0011(6) O2 0.0228(8) 0.0197(8) 0.0209(7) -0.0045(6) 0.0048(6) -0.0042(6) Cu1 0.01877(19) 0.01588(18) 0.01673(17) -0.00222(14) 0.00103(16) -0.00082(15) Cl1 0.0628(5) 0.0260(3) 0.0612(4) -0.0065(3) -0.0114(4) 0.0084(3) Cl2 0.0450(4) 0.0359(4) 0.0422(3) -0.0020(3) -0.0002(3) -0.0111(3) Cl3 0.0417(4) 0.0559(4) 0.0395(3) -0.0109(3) -0.0101(3) 0.0176(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 C1 C2 1.495(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.379(3) . ? C2 C3 1.381(3) . ? C3 O2 1.322(3) . ? C3 C4 1.428(3) . ? C4 O1 1.308(2) . ? C4 C5 1.395(3) . ? C5 C6 1.362(3) . ? C5 H5 0.9500 . ? C6 N1 1.352(3) . ? C6 H6 0.9500 . ? C7 C12 1.378(3) . ? C7 C8 1.381(3) . ? C7 N1 1.453(3) . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 C10 1.376(4) . ? C9 H9 0.9500 . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 Cl2 1.751(2) . ? C13 Cl3 1.752(2) . ? C13 Cl1 1.757(2) . ? C13 H13 1.0000 . ? O1 Cu1 1.9275(15) . ? O2 Cu1 1.9096(14) . ? Cu1 O2 1.9096(14) 5_656 ? Cu1 O1 1.9275(15) 5_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 118.67(19) . . ? N1 C2 C1 120.23(18) . . ? C3 C2 C1 121.04(19) . . ? O2 C3 C2 122.87(19) . . ? O2 C3 C4 117.03(18) . . ? C2 C3 C4 120.10(19) . . ? O1 C4 C5 124.24(19) . . ? O1 C4 C3 117.16(19) . . ? C5 C4 C3 118.59(19) . . ? C6 C5 C4 119.4(2) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N1 C6 C5 121.7(2) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C12 C7 C8 121.0(2) . . ? C12 C7 N1 120.0(2) . . ? C8 C7 N1 119.0(2) . . ? C7 C8 C9 119.2(2) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.2(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C7 C12 C11 119.6(2) . . ? C7 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? Cl2 C13 Cl3 111.63(13) . . ? Cl2 C13 Cl1 109.72(14) . . ? Cl3 C13 Cl1 109.77(13) . . ? Cl2 C13 H13 108.5 . . ? Cl3 C13 H13 108.5 . . ? Cl1 C13 H13 108.5 . . ? C6 N1 C2 121.49(18) . . ? C6 N1 C7 117.19(18) . . ? C2 N1 C7 121.32(17) . . ? C4 O1 Cu1 109.65(13) . . ? C3 O2 Cu1 109.70(12) . . ? O2 Cu1 O2 180.00(6) . 5_656 ? O2 Cu1 O1 93.62(6) . 5_656 ? O2 Cu1 O1 86.38(6) 5_656 5_656 ? O2 Cu1 O1 86.38(6) . . ? O2 Cu1 O1 93.62(6) 5_656 . ? O1 Cu1 O1 180.00(6) 5_656 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 179.90(18) . . . . ? C1 C2 C3 O2 -2.7(3) . . . . ? N1 C2 C3 C4 -1.3(3) . . . . ? C1 C2 C3 C4 176.1(2) . . . . ? O2 C3 C4 O1 -1.7(3) . . . . ? C2 C3 C4 O1 179.37(19) . . . . ? O2 C3 C4 C5 178.53(19) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? O1 C4 C5 C6 -177.9(2) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C4 C5 C6 N1 -1.6(3) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? N1 C7 C8 C9 -178.77(19) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C8 C7 C12 C11 0.6(3) . . . . ? N1 C7 C12 C11 179.3(2) . . . . ? C10 C11 C12 C7 -0.2(4) . . . . ? C5 C6 N1 C2 -0.1(3) . . . . ? C5 C6 N1 C7 179.4(2) . . . . ? C3 C2 N1 C6 1.5(3) . . . . ? C1 C2 N1 C6 -175.9(2) . . . . ? C3 C2 N1 C7 -177.97(19) . . . . ? C1 C2 N1 C7 4.6(3) . . . . ? C12 C7 N1 C6 -116.0(2) . . . . ? C8 C7 N1 C6 62.7(3) . . . . ? C12 C7 N1 C2 63.5(3) . . . . ? C8 C7 N1 C2 -117.8(2) . . . . ? C5 C4 O1 Cu1 179.42(17) . . . . ? C3 C4 O1 Cu1 -0.3(2) . . . . ? C2 C3 O2 Cu1 -178.35(17) . . . . ? C4 C3 O2 Cu1 2.8(2) . . . . ? C3 O2 Cu1 O2 -104.32(16) . . . 5_656 ? C3 O2 Cu1 O1 177.67(14) . . . 5_656 ? C3 O2 Cu1 O1 -2.33(14) . . . . ? C4 O1 Cu1 O2 1.45(13) . . . . ? C4 O1 Cu1 O2 -178.55(13) . . . 5_656 ? C4 O1 Cu1 O1 68.26(11) . . . 5_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.320 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.063 # Attachment 'Hnbp.cif' data_co348 _database_code_depnum_ccdc_archive 'CCDC 697418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cl3 N O2' _chemical_formula_weight 334.61 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' 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 11.7981(13) _cell_length_b 10.8093(13) _cell_length_c 12.5786(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.760(6) _cell_angle_gamma 90.00 _cell_volume 1527.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6917 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 27.71 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details 'SADABS (Bruker Nonius, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16003 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 28.01 _reflns_number_total 3665 _reflns_number_gt 2742 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0370P)^2^+1.3583P] 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 3665 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.20362(18) 0.0996(2) 0.17490(18) 0.0337(5) Uani 1 1 d . . . H1A H 0.1954 0.0558 0.2404 0.050 Uiso 1 1 calc R . . H1B H 0.1824 0.0439 0.1104 0.050 Uiso 1 1 calc R . . H1C H 0.1506 0.1715 0.1591 0.050 Uiso 1 1 calc R . . C2 C 0.32900(16) 0.14147(18) 0.19752(15) 0.0253(4) Uani 1 1 d . . . C3 C 0.39900(16) 0.09695(17) 0.13783(14) 0.0231(4) Uani 1 1 d . . . C4 C 0.51781(16) 0.13867(19) 0.15467(16) 0.0279(4) Uani 1 1 d . . . C5 C 0.55927(18) 0.2265(2) 0.24078(17) 0.0348(5) Uani 1 1 d . . . H5 H 0.6384 0.2568 0.2581 0.042 Uiso 1 1 calc R . . C6 C 0.48773(19) 0.2682(2) 0.29905(18) 0.0358(5) Uani 1 1 d . . . H6 H 0.5180 0.3277 0.3562 0.043 Uiso 1 1 calc R . . C7 C 0.3018(2) 0.2793(2) 0.34462(19) 0.0367(5) Uani 1 1 d . . . H7A H 0.2232 0.3035 0.2932 0.044 Uiso 1 1 calc R . . H7B H 0.3406 0.3548 0.3836 0.044 Uiso 1 1 calc R . . C8 C 0.28365(19) 0.18951(19) 0.42930(17) 0.0330(5) Uani 1 1 d . . . C9 C 0.1735(2) 0.1800(2) 0.44591(19) 0.0409(5) Uani 1 1 d . . . H9 H 0.1088 0.2281 0.4019 0.049 Uiso 1 1 calc R . . C10 C 0.1570(2) 0.1010(3) 0.5261(2) 0.0509(6) Uani 1 1 d . . . H10 H 0.0809 0.0950 0.5369 0.061 Uiso 1 1 calc R . . C11 C 0.2497(3) 0.0313(2) 0.5901(2) 0.0531(7) Uani 1 1 d . . . H11 H 0.2380 -0.0233 0.6450 0.064 Uiso 1 1 calc R . . C12 C 0.3597(3) 0.0407(3) 0.5744(2) 0.0529(7) Uani 1 1 d . . . H12 H 0.4243 -0.0073 0.6189 0.063 Uiso 1 1 calc R . . C13 C 0.3764(2) 0.1193(2) 0.49463(19) 0.0428(5) Uani 1 1 d . . . H13 H 0.4527 0.1253 0.4844 0.051 Uiso 1 1 calc R . . C14 C -0.16389(19) 0.1759(2) 0.10936(18) 0.0372(5) Uani 1 1 d . . . H14 H -0.2516 0.1614 0.0888 0.045 Uiso 1 1 calc R . . N1 N 0.37517(15) 0.22812(15) 0.27879(14) 0.0301(4) Uani 1 1 d . . . O1 O 0.57806(12) 0.09722(15) 0.09472(12) 0.0375(4) Uani 1 1 d . . . O2 O 0.35190(12) 0.01193(13) 0.05798(11) 0.0272(3) Uani 1 1 d . . . Cl1 Cl -0.12753(8) 0.30579(8) 0.19704(7) 0.0725(3) Uani 1 1 d . . . Cl2 Cl -0.12581(6) 0.20340(7) -0.01193(5) 0.05458(19) Uani 1 1 d . . . Cl3 Cl -0.08982(6) 0.04570(7) 0.17945(7) 0.0655(2) Uani 1 1 d . . . H2O H 0.392(2) -0.004(2) 0.024(2) 0.035(7) 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 C1 0.0317(10) 0.0366(11) 0.0362(11) -0.0052(9) 0.0156(9) -0.0027(9) C2 0.0302(9) 0.0233(9) 0.0235(9) 0.0005(8) 0.0096(8) 0.0011(8) C3 0.0268(9) 0.0218(9) 0.0197(8) -0.0005(7) 0.0056(7) -0.0001(7) C4 0.0269(9) 0.0294(10) 0.0265(10) -0.0036(8) 0.0071(8) -0.0012(8) C5 0.0313(10) 0.0381(11) 0.0335(11) -0.0112(9) 0.0079(9) -0.0071(9) C6 0.0435(12) 0.0323(11) 0.0319(11) -0.0131(9) 0.0121(9) -0.0085(9) C7 0.0481(12) 0.0295(11) 0.0387(11) -0.0086(9) 0.0224(10) 0.0053(9) C8 0.0412(11) 0.0318(11) 0.0296(10) -0.0103(9) 0.0160(9) 0.0011(9) C9 0.0403(12) 0.0439(13) 0.0404(12) -0.0067(10) 0.0154(10) 0.0023(10) C10 0.0539(15) 0.0517(15) 0.0573(16) -0.0108(13) 0.0319(13) -0.0082(12) C11 0.0838(19) 0.0404(13) 0.0486(15) -0.0008(12) 0.0404(15) 0.0018(13) C12 0.0698(17) 0.0516(15) 0.0429(14) 0.0054(12) 0.0257(13) 0.0194(13) C13 0.0465(13) 0.0466(14) 0.0409(12) -0.0026(11) 0.0216(11) 0.0100(11) C14 0.0322(10) 0.0409(12) 0.0387(12) -0.0049(10) 0.0114(9) -0.0086(9) N1 0.0382(9) 0.0253(8) 0.0302(9) -0.0070(7) 0.0156(7) -0.0004(7) O1 0.0282(7) 0.0488(9) 0.0381(8) -0.0196(7) 0.0139(6) -0.0071(6) O2 0.0271(7) 0.0302(7) 0.0259(7) -0.0086(6) 0.0102(6) -0.0043(6) Cl1 0.0807(5) 0.0701(5) 0.0698(5) -0.0356(4) 0.0274(4) -0.0240(4) Cl2 0.0638(4) 0.0583(4) 0.0464(3) -0.0041(3) 0.0239(3) -0.0189(3) Cl3 0.0407(3) 0.0632(4) 0.0892(5) 0.0300(4) 0.0149(3) -0.0039(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 C1 C2 1.489(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.362(3) . ? C2 N1 1.371(3) . ? C3 O2 1.350(2) . ? C3 C4 1.425(3) . ? C4 O1 1.266(2) . ? C4 C5 1.411(3) . ? C5 C6 1.353(3) . ? C5 H5 0.9500 . ? C6 N1 1.345(3) . ? C6 H6 0.9500 . ? C7 N1 1.476(2) . ? C7 C8 1.504(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.379(3) . ? C8 C9 1.381(3) . ? C9 C10 1.379(4) . ? C9 H9 0.9500 . ? C10 C11 1.369(4) . ? C10 H10 0.9500 . ? C11 C12 1.375(4) . ? C11 H11 0.9500 . ? C12 C13 1.375(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 Cl2 1.742(2) . ? C14 Cl3 1.747(2) . ? C14 Cl1 1.756(2) . ? C14 H14 1.0000 . ? O2 H2O 0.75(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 118.85(17) . . ? C3 C2 C1 121.42(17) . . ? N1 C2 C1 119.72(16) . . ? O2 C3 C2 118.00(16) . . ? O2 C3 C4 119.27(16) . . ? C2 C3 C4 122.71(17) . . ? O1 C4 C5 124.71(18) . . ? O1 C4 C3 120.34(17) . . ? C5 C4 C3 114.95(17) . . ? C6 C5 C4 120.82(19) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? N1 C6 C5 122.24(19) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? N1 C7 C8 112.96(17) . . ? N1 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C13 C8 C9 118.7(2) . . ? C13 C8 C7 121.3(2) . . ? C9 C8 C7 119.9(2) . . ? C10 C9 C8 120.4(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 120.7(2) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? Cl2 C14 Cl3 110.88(13) . . ? Cl2 C14 Cl1 109.56(12) . . ? Cl3 C14 Cl1 109.79(13) . . ? Cl2 C14 H14 108.9 . . ? Cl3 C14 H14 108.9 . . ? Cl1 C14 H14 108.9 . . ? C6 N1 C2 120.39(16) . . ? C6 N1 C7 119.16(17) . . ? C2 N1 C7 120.45(17) . . ? C3 O2 H2O 113.3(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 -179.84(16) . . . . ? C1 C2 C3 O2 -0.9(3) . . . . ? N1 C2 C3 C4 -1.4(3) . . . . ? C1 C2 C3 C4 177.57(18) . . . . ? O2 C3 C4 O1 0.6(3) . . . . ? C2 C3 C4 O1 -177.81(19) . . . . ? O2 C3 C4 C5 -179.36(18) . . . . ? C2 C3 C4 C5 2.2(3) . . . . ? O1 C4 C5 C6 178.3(2) . . . . ? C3 C4 C5 C6 -1.7(3) . . . . ? C4 C5 C6 N1 0.4(4) . . . . ? N1 C7 C8 C13 43.7(3) . . . . ? N1 C7 C8 C9 -139.0(2) . . . . ? C13 C8 C9 C10 -0.3(3) . . . . ? C7 C8 C9 C10 -177.8(2) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C8 0.0(4) . . . . ? C9 C8 C13 C12 0.3(3) . . . . ? C7 C8 C13 C12 177.7(2) . . . . ? C5 C6 N1 C2 0.5(3) . . . . ? C5 C6 N1 C7 -179.0(2) . . . . ? C3 C2 N1 C6 -0.1(3) . . . . ? C1 C2 N1 C6 -179.03(19) . . . . ? C3 C2 N1 C7 179.51(18) . . . . ? C1 C2 N1 C7 0.5(3) . . . . ? C8 C7 N1 C6 -106.5(2) . . . . ? C8 C7 N1 C2 73.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.718 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.052