# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wubiao@lzb.ac.cn _publ_contact_author_name 'Biao Wu' _publ_author_name 'Biao Wu' data_CuAcL _database_code_depnum_ccdc_archive 'CCDC 828239' #TrackingRef '- bisurea complexes-R1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H31.20 Cu2 N6 O11.60' _chemical_formula_weight 668.39 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0028(11) _cell_length_b 11.9202(13) _cell_length_c 14.3524(16) _cell_angle_alpha 99.7760(10) _cell_angle_beta 102.1300(10) _cell_angle_gamma 110.143(2) _cell_volume 1515.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description stick _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.466 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7581 _exptl_absorpt_correction_T_max 0.8673 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10050 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5227 _reflns_number_gt 3875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.497 0.500 1.000 221 12 ' ' _platon_squeeze_details ; ; _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^)+(0.0579P)^2^+0.0200P] 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 5227 _refine_ls_number_parameters 371 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.47180(5) 0.41687(4) 0.40164(3) 0.03548(15) Uani 1 1 d . . . Cu2 Cu 0.58183(5) 0.69100(4) 0.40371(3) 0.03526(15) Uani 1 1 d D . . O1 O 1.1094(3) 0.9190(3) 0.1554(2) 0.0506(7) Uani 1 1 d . . . O2 O 1.1824(4) 0.8652(3) -0.1182(2) 0.0632(9) Uani 1 1 d . . . O3 O 0.7221(3) 0.6047(2) 0.4285(2) 0.0419(7) Uani 1 1 d . . . O4 O 0.7738(3) 0.7264(3) 0.5763(2) 0.0517(8) Uani 1 1 d . . . O5 O 0.4706(3) 0.7981(2) 0.4065(2) 0.0464(7) Uani 1 1 d . . . O6 O 0.2516(3) 0.6545(3) 0.3985(3) 0.0707(10) Uani 1 1 d . . . O7 O 0.3494(3) 0.3914(2) 0.26910(19) 0.0486(7) Uani 1 1 d . . . O8 O 0.4567(3) 0.5771(3) 0.2463(2) 0.0555(8) Uani 1 1 d . . . O9 O 0.4518(3) 0.5705(2) 0.45774(18) 0.0319(6) Uani 1 1 d D . . O10 O 0.2029(6) 0.7604(5) 0.0456(3) 0.1114(16) Uani 1 1 d D . . O11 O 0.4782(4) 0.7660(3) 0.1410(3) 0.0834(11) Uani 1 1 d D . . N1 N 0.7339(4) 0.8088(3) 0.3598(2) 0.0397(8) Uani 1 1 d . . . N2 N 1.0709(4) 1.0483(3) 0.2736(2) 0.0417(8) Uani 1 1 d . . . H2A H 1.1061 1.1241 0.3077 0.050 Uiso 1 1 calc R . . N3 N 1.2132(4) 1.1249(3) 0.1751(2) 0.0446(8) Uani 1 1 d . . . H3A H 1.2182 1.1965 0.2034 0.054 Uiso 1 1 calc R . . N4 N 1.2823(4) 1.0747(3) -0.0715(2) 0.0489(9) Uani 1 1 d . . . H4A H 1.3445 1.1410 -0.0789 0.059 Uiso 1 1 calc R . . N5 N 1.3491(4) 0.9750(3) -0.1906(2) 0.0467(9) Uani 1 1 d . . . H5A H 1.3935 1.0483 -0.1963 0.056 Uiso 1 1 calc R . . N6 N 1.4489(4) 0.7050(3) -0.3521(2) 0.0403(8) Uani 1 1 d . . . C1 C 0.7979(5) 0.9307(4) 0.4014(3) 0.0456(10) Uani 1 1 d . . . H2 H 0.7643 0.9635 0.4509 0.055 Uiso 1 1 calc R . . C2 C 0.9099(5) 1.0094(4) 0.3750(3) 0.0453(10) Uani 1 1 d . . . H3 H 0.9515 1.0935 0.4072 0.054 Uiso 1 1 calc R . . C3 C 0.9627(4) 0.9657(3) 0.3004(3) 0.0348(9) Uani 1 1 d . . . C4 C 0.8970(5) 0.8392(4) 0.2572(3) 0.0455(10) Uani 1 1 d . . . H4 H 0.9281 0.8037 0.2075 0.055 Uiso 1 1 calc R . . C5 C 0.7855(5) 0.7673(4) 0.2889(3) 0.0482(11) Uani 1 1 d . . . H5 H 0.7423 0.6827 0.2585 0.058 Uiso 1 1 calc R . . C6 C 1.1303(4) 1.0237(4) 0.1979(3) 0.0379(9) Uani 1 1 d . . . C7 C 1.2942(4) 1.1147(4) 0.1034(3) 0.0455(10) Uani 1 1 d . . . H7A H 1.3312 1.0502 0.1097 0.055 Uiso 1 1 calc R . . H7B H 1.3793 1.1921 0.1174 0.055 Uiso 1 1 calc R . . C8 C 1.1989(5) 1.0849(4) -0.0011(3) 0.0499(11) Uani 1 1 d . . . H8A H 1.1137 1.0074 -0.0155 0.060 Uiso 1 1 calc R . . H8B H 1.1622 1.1494 -0.0079 0.060 Uiso 1 1 calc R . . C9 C 1.2645(5) 0.9648(4) -0.1249(3) 0.0436(10) Uani 1 1 d . . . C10 C 1.3704(4) 0.8801(4) -0.2481(3) 0.0379(9) Uani 1 1 d . . . C11 C 1.4631(5) 0.9114(4) -0.3079(3) 0.0444(10) Uani 1 1 d . . . H11 H 1.4996 0.9918 -0.3144 0.053 Uiso 1 1 calc R . . C12 C 1.5001(5) 0.8233(4) -0.3567(3) 0.0450(10) Uani 1 1 d . . . H12 H 1.5639 0.8463 -0.3951 0.054 Uiso 1 1 calc R . . C13 C 1.3533(5) 0.6737(4) -0.2996(3) 0.0504(11) Uani 1 1 d . . . H13 H 1.3138 0.5914 -0.2977 0.060 Uiso 1 1 calc R . . C14 C 1.3095(5) 0.7565(4) -0.2477(3) 0.0465(10) Uani 1 1 d . . . H14 H 1.2408 0.7301 -0.2132 0.056 Uiso 1 1 calc R . . C15 C 0.8016(5) 0.6532(4) 0.5182(3) 0.0436(10) Uani 1 1 d . . . C16 C 0.9305(5) 0.6212(5) 0.5516(4) 0.0795(17) Uani 1 1 d . . . H16A H 0.9872 0.6297 0.5049 0.119 Uiso 1 1 calc R . . H16B H 0.8961 0.5372 0.5563 0.119 Uiso 1 1 calc R . . H16C H 0.9922 0.6757 0.6151 0.119 Uiso 1 1 calc R . . C17 C 0.3316(5) 0.7593(4) 0.3991(3) 0.0491(11) Uani 1 1 d . . . C18 C 0.2655(6) 0.8550(5) 0.3939(4) 0.0815(17) Uani 1 1 d . . . H18A H 0.2432 0.8627 0.3275 0.122 Uiso 1 1 calc R . . H18B H 0.3355 0.9334 0.4376 0.122 Uiso 1 1 calc R . . H18C H 0.1758 0.8299 0.4134 0.122 Uiso 1 1 calc R . . C19 C 0.3579(5) 0.4734(4) 0.2217(3) 0.0519(11) Uani 1 1 d . . . C20 C 0.2326(8) 0.4371(6) 0.1295(4) 0.121(3) Uani 1 1 d . . . H20A H 0.1856 0.4949 0.1339 0.181 Uiso 1 1 calc R . . H20B H 0.1612 0.3555 0.1221 0.181 Uiso 1 1 calc R . . H20C H 0.2708 0.4375 0.0735 0.181 Uiso 1 1 calc R . . H11A H 0.462(5) 0.702(3) 0.165(3) 0.080 Uiso 1 1 d D . . H11B H 0.387(3) 0.743(4) 0.105(3) 0.080 Uiso 1 1 d D . . H10A H 0.186(6) 0.793(4) -0.008(2) 0.080 Uiso 1 1 d D . . H10B H 0.189(6) 0.690(3) 0.006(3) 0.080 Uiso 1 1 d D . . H21 H 0.366(2) 0.573(3) 0.446(3) 0.066(15) Uiso 1 1 d 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 Cu1 0.0452(3) 0.0260(3) 0.0380(3) 0.0074(2) 0.0153(2) 0.0160(2) Cu2 0.0400(3) 0.0263(3) 0.0443(3) 0.0134(2) 0.0195(2) 0.0124(2) O1 0.061(2) 0.0342(17) 0.0562(17) 0.0094(14) 0.0307(15) 0.0119(15) O2 0.075(2) 0.051(2) 0.073(2) 0.0158(17) 0.0448(19) 0.0226(19) O3 0.0473(17) 0.0335(15) 0.0510(17) 0.0133(13) 0.0224(15) 0.0175(14) O4 0.0460(18) 0.0425(18) 0.0545(17) 0.0011(14) 0.0126(15) 0.0098(15) O5 0.0511(19) 0.0370(16) 0.0665(19) 0.0236(14) 0.0296(15) 0.0235(15) O6 0.0432(19) 0.049(2) 0.128(3) 0.041(2) 0.025(2) 0.0201(17) O7 0.061(2) 0.0307(16) 0.0451(16) 0.0090(13) 0.0062(14) 0.0136(15) O8 0.066(2) 0.0393(18) 0.0440(16) 0.0119(14) 0.0108(15) 0.0024(17) O9 0.0325(15) 0.0237(13) 0.0403(14) 0.0094(11) 0.0133(12) 0.0101(12) O10 0.160(4) 0.126(4) 0.092(3) 0.043(3) 0.045(3) 0.097(4) O11 0.089(3) 0.063(2) 0.092(3) 0.043(2) 0.020(2) 0.016(2) N1 0.045(2) 0.0314(18) 0.0447(18) 0.0139(15) 0.0189(16) 0.0123(16) N2 0.045(2) 0.0298(18) 0.0445(18) 0.0037(15) 0.0220(16) 0.0053(16) N3 0.051(2) 0.036(2) 0.0406(18) 0.0046(15) 0.0216(17) 0.0068(17) N4 0.065(2) 0.043(2) 0.048(2) 0.0117(16) 0.0305(19) 0.0247(19) N5 0.065(2) 0.042(2) 0.0462(19) 0.0155(16) 0.0302(18) 0.0266(19) N6 0.049(2) 0.038(2) 0.0406(18) 0.0084(15) 0.0195(16) 0.0225(17) C1 0.053(3) 0.034(2) 0.050(2) 0.0076(19) 0.029(2) 0.012(2) C2 0.053(3) 0.028(2) 0.048(2) 0.0024(18) 0.022(2) 0.007(2) C3 0.034(2) 0.035(2) 0.035(2) 0.0111(17) 0.0114(17) 0.0120(18) C4 0.051(3) 0.038(2) 0.051(2) 0.0092(19) 0.030(2) 0.013(2) C5 0.055(3) 0.030(2) 0.056(3) 0.0068(19) 0.023(2) 0.011(2) C6 0.035(2) 0.038(2) 0.035(2) 0.0063(18) 0.0084(18) 0.0098(19) C7 0.040(2) 0.050(3) 0.040(2) 0.0093(19) 0.0150(19) 0.011(2) C8 0.055(3) 0.055(3) 0.045(2) 0.010(2) 0.023(2) 0.025(2) C9 0.052(3) 0.047(3) 0.039(2) 0.012(2) 0.018(2) 0.024(2) C10 0.045(2) 0.037(2) 0.037(2) 0.0089(17) 0.0126(19) 0.022(2) C11 0.065(3) 0.032(2) 0.045(2) 0.0110(18) 0.025(2) 0.023(2) C12 0.059(3) 0.040(2) 0.044(2) 0.0129(19) 0.024(2) 0.022(2) C13 0.057(3) 0.034(2) 0.061(3) 0.007(2) 0.026(2) 0.016(2) C14 0.047(3) 0.045(3) 0.049(2) 0.010(2) 0.023(2) 0.016(2) C15 0.039(2) 0.028(2) 0.065(3) 0.019(2) 0.022(2) 0.0076(19) C16 0.048(3) 0.064(3) 0.127(5) 0.029(3) 0.013(3) 0.029(3) C17 0.051(3) 0.047(3) 0.062(3) 0.022(2) 0.017(2) 0.029(2) C18 0.079(4) 0.079(4) 0.122(5) 0.052(4) 0.047(4) 0.052(3) C19 0.066(3) 0.038(3) 0.043(2) 0.009(2) 0.006(2) 0.017(3) C20 0.128(6) 0.073(4) 0.097(5) 0.034(4) -0.048(4) 0.005(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 Cu1 O7 1.944(3) . ? Cu1 O9 1.962(2) 2_666 ? Cu1 O9 1.965(2) . ? Cu1 N6 1.981(3) 2_765 ? Cu1 Cu1 2.9795(9) 2_666 ? Cu2 O5 1.962(3) . ? Cu2 O9 1.967(3) . ? Cu2 N1 1.978(3) . ? Cu2 O3 2.015(3) . ? Cu2 O8 2.261(3) . ? O1 C6 1.217(4) . ? O2 C9 1.222(5) . ? O3 C15 1.275(5) . ? O4 C15 1.245(5) . ? O5 C17 1.280(5) . ? O6 C17 1.228(5) . ? O7 C19 1.272(5) . ? O8 C19 1.221(5) . ? O9 Cu1 1.962(2) 2_666 ? O9 H21 0.851(18) . ? O10 H10A 0.925(19) . ? O10 H10B 0.880(19) . ? O11 H11A 0.869(19) . ? O11 H11B 0.864(19) . ? N1 C5 1.332(5) . ? N1 C1 1.335(5) . ? N2 C3 1.364(5) . ? N2 C6 1.379(5) . ? N2 H2A 0.8600 . ? N3 C6 1.345(5) . ? N3 C7 1.453(5) . ? N3 H3A 0.8600 . ? N4 C9 1.333(5) . ? N4 C8 1.454(5) . ? N4 H4A 0.8600 . ? N5 C9 1.386(5) . ? N5 C10 1.389(5) . ? N5 H5A 0.8600 . ? N6 C13 1.333(5) . ? N6 C12 1.343(5) . ? N6 Cu1 1.981(3) 2_765 ? C1 C2 1.362(5) . ? C1 H2 0.9300 . ? C2 C3 1.391(5) . ? C2 H3 0.9300 . ? C3 C4 1.385(5) . ? C4 C5 1.368(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.506(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C14 1.389(5) . ? C10 C11 1.393(6) . ? C11 C12 1.362(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.380(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.477(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.507(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.498(7) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O7 Cu1 O9 165.93(12) . 2_666 ? O7 Cu1 O9 94.98(10) . . ? O9 Cu1 O9 81.30(10) 2_666 . ? O7 Cu1 N6 91.19(12) . 2_765 ? O9 Cu1 N6 96.08(11) 2_666 2_765 ? O9 Cu1 N6 163.67(13) . 2_765 ? O7 Cu1 Cu1 134.10(8) . 2_666 ? O9 Cu1 Cu1 40.69(7) 2_666 2_666 ? O9 Cu1 Cu1 40.61(7) . 2_666 ? N6 Cu1 Cu1 134.64(9) 2_765 2_666 ? O5 Cu2 O9 94.47(11) . . ? O5 Cu2 N1 91.30(12) . . ? O9 Cu2 N1 172.66(12) . . ? O5 Cu2 O3 168.15(12) . . ? O9 Cu2 O3 86.35(10) . . ? N1 Cu2 O3 87.07(12) . . ? O5 Cu2 O8 95.45(12) . . ? O9 Cu2 O8 92.39(11) . . ? N1 Cu2 O8 91.57(12) . . ? O3 Cu2 O8 96.32(11) . . ? C15 O3 Cu2 106.6(2) . . ? C17 O5 Cu2 123.9(3) . . ? C19 O7 Cu1 126.0(3) . . ? C19 O8 Cu2 125.4(3) . . ? Cu1 O9 Cu1 98.70(10) 2_666 . ? Cu1 O9 Cu2 116.14(12) 2_666 . ? Cu1 O9 Cu2 102.21(11) . . ? Cu1 O9 H21 110(3) 2_666 . ? Cu1 O9 H21 119(3) . . ? Cu2 O9 H21 110.3(18) . . ? H10A O10 H10B 90(2) . . ? H11A O11 H11B 96(3) . . ? C5 N1 C1 115.7(4) . . ? C5 N1 Cu2 120.2(3) . . ? C1 N1 Cu2 123.9(3) . . ? C3 N2 C6 127.2(3) . . ? C3 N2 H2A 116.4 . . ? C6 N2 H2A 116.4 . . ? C6 N3 C7 120.7(3) . . ? C6 N3 H3A 119.6 . . ? C7 N3 H3A 119.6 . . ? C9 N4 C8 121.4(4) . . ? C9 N4 H4A 119.3 . . ? C8 N4 H4A 119.3 . . ? C9 N5 C10 127.3(4) . . ? C9 N5 H5A 116.3 . . ? C10 N5 H5A 116.3 . . ? C13 N6 C12 117.0(3) . . ? C13 N6 Cu1 118.5(3) . 2_765 ? C12 N6 Cu1 123.9(3) . 2_765 ? N1 C1 C2 123.2(4) . . ? N1 C1 H2 118.4 . . ? C2 C1 H2 118.4 . . ? C1 C2 C3 120.8(4) . . ? C1 C2 H3 119.6 . . ? C3 C2 H3 119.6 . . ? N2 C3 C4 124.8(3) . . ? N2 C3 C2 118.9(3) . . ? C4 C3 C2 116.2(4) . . ? C5 C4 C3 118.8(4) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 125.2(4) . . ? N1 C5 H5 117.4 . . ? C4 C5 H5 117.4 . . ? O1 C6 N3 122.9(4) . . ? O1 C6 N2 122.7(4) . . ? N3 C6 N2 114.4(3) . . ? N3 C7 C8 112.3(3) . . ? N3 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N3 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N4 C8 C7 111.2(3) . . ? N4 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N4 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O2 C9 N4 124.5(4) . . ? O2 C9 N5 123.0(4) . . ? N4 C9 N5 112.6(4) . . ? C14 C10 N5 124.4(4) . . ? C14 C10 C11 117.6(3) . . ? N5 C10 C11 117.9(4) . . ? C12 C11 C10 119.5(4) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? N6 C12 C11 123.3(4) . . ? N6 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? N6 C13 C14 123.7(4) . . ? N6 C13 H13 118.1 . . ? C14 C13 H13 118.1 . . ? C13 C14 C10 118.6(4) . . ? C13 C14 H14 120.7 . . ? C10 C14 H14 120.7 . . ? O4 C15 O3 121.8(4) . . ? O4 C15 C16 120.4(4) . . ? O3 C15 C16 117.8(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O6 C17 O5 125.9(4) . . ? O6 C17 C18 118.9(4) . . ? O5 C17 C18 115.1(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O8 C19 O7 125.5(4) . . ? O8 C19 C20 119.1(4) . . ? O7 C19 C20 115.4(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 H2A O4 0.86 2.02 2.833(4) 158.0 2_776 N3 H3A O7 0.86 2.15 2.925(4) 148.9 1_665 N4 H4A O11 0.86 2.19 2.975(5) 150.8 2_775 N5 H5A O11 0.86 2.05 2.844(5) 153.5 2_775 O10 H10A O2 0.925(19) 1.93(2) 2.845(5) 171(5) 1_455 C13 H13 O3 0.93 2.60 3.258(5) 128.0 2_765 O11 H11A O8 0.869(19) 2.04(2) 2.892(5) 168(4) . O11 H11B O10 0.864(19) 1.96(2) 2.779(6) 157(5) . C4 H4 O1 0.93 2.22 2.818(5) 121.1 . C8 H8A O2 0.97 2.43 2.793(5) 101.8 . C14 H14 O2 0.93 2.24 2.839(5) 121.3 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.640 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.069 ##################### data_CuAcL-2 _database_code_depnum_ccdc_archive 'CCDC 828240' #TrackingRef '- bisurea complexes-R1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H54 Cu N12 O13' _chemical_formula_weight 914.44 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' _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 24.550(18) _cell_length_b 15.285(11) _cell_length_c 14.484(10) _cell_angle_alpha 90.00 _cell_angle_beta 122.935(10) _cell_angle_gamma 90.00 _cell_volume 4561(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1924 _exptl_absorpt_coefficient_mu 0.550 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8979 _exptl_absorpt_correction_T_max 0.9220 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10311 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0796 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3979 _reflns_number_gt 2214 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1136P)^2^+4.3215P] 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 3979 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1313 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.2222 _refine_ls_wR_factor_gt 0.1820 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Cu Cu 0.5000 0.77769(6) 0.7500 0.0529(4) Uani 1 2 d S . . O1 O 0.3144(2) 0.4785(3) 0.8437(3) 0.0706(12) Uani 1 1 d . . . O2 O 0.36628(19) 0.1203(2) 0.8918(3) 0.0634(11) Uani 1 1 d . . . O3 O 0.5454(2) 0.7652(3) 0.9600(4) 0.0804(14) Uani 1 1 d . . . H3C H 0.5322 0.7310 0.9946 0.080 Uiso 1 1 d R . . H3B H 0.5640 0.8103 1.0126 0.080 Uiso 1 1 d R . . O4 O 0.2241(2) 0.1313(3) 0.4908(3) 0.0652(11) Uani 1 1 d . . . O5 O 0.1756(2) 0.2248(3) 0.5414(4) 0.0872(15) Uani 1 1 d . . . O6 O 0.5319(10) 0.6215(17) 0.0652(11) 0.294(15) Uani 0.50 1 d P . . O7 O 0.4348(4) 0.2008(5) 0.5114(7) 0.155(3) Uani 1 1 d . . . H7 H 0.4458 0.1927 0.4677 0.232 Uiso 1 1 calc R . . N1 N 0.4342(2) 0.6855(3) 0.7252(4) 0.0486(11) Uani 1 1 d . . . N2 N 0.3041(2) 0.4854(3) 0.6773(4) 0.0539(12) Uani 1 1 d . . . H2A H 0.2837 0.4625 0.6127 0.065 Uiso 1 1 calc R . . N3 N 0.2501(2) 0.3821(3) 0.7095(4) 0.0537(12) Uani 1 1 d . . . H3A H 0.2333 0.3681 0.6417 0.064 Uiso 1 1 calc R . . N4 N 0.2782(2) 0.1938(3) 0.7589(4) 0.0523(12) Uani 1 1 d . . . H4A H 0.2485 0.1974 0.6900 0.063 Uiso 1 1 calc R . . N5 N 0.3190(2) 0.0810(3) 0.7104(3) 0.0493(11) Uani 1 1 d . . . H5A H 0.2878 0.0932 0.6444 0.059 Uiso 1 1 calc R . . N6 N 0.4383(2) -0.1267(3) 0.7339(4) 0.0506(11) Uani 1 1 d . . . C1 C 0.4122(3) 0.6258(4) 0.6441(5) 0.0600(16) Uani 1 1 d . . . H1 H 0.4275 0.6282 0.5978 0.072 Uiso 1 1 calc R . . C2 C 0.3685(3) 0.5615(4) 0.6265(5) 0.0592(16) Uani 1 1 d . . . H2 H 0.3538 0.5233 0.5675 0.071 Uiso 1 1 calc R . . C3 C 0.3461(2) 0.5529(3) 0.6956(4) 0.0432(13) Uani 1 1 d . . . C4 C 0.3674(2) 0.6149(3) 0.7781(4) 0.0496(14) Uani 1 1 d . . . H4 H 0.3528 0.6135 0.8254 0.060 Uiso 1 1 calc R . . C5 C 0.4101(2) 0.6783(4) 0.7896(4) 0.0488(13) Uani 1 1 d . . . H5 H 0.4236 0.7191 0.8456 0.059 Uiso 1 1 calc R . . C6 C 0.2912(3) 0.4507(3) 0.7507(5) 0.0499(14) Uani 1 1 d . . . C7 C 0.2328(3) 0.3311(3) 0.7741(5) 0.0586(16) Uani 1 1 d . . . H7A H 0.1893 0.3082 0.7257 0.070 Uiso 1 1 calc R . . H7B H 0.2322 0.3693 0.8270 0.070 Uiso 1 1 calc R . . C8 C 0.2785(3) 0.2555(4) 0.8353(5) 0.0598(16) Uani 1 1 d . . . H8A H 0.3222 0.2777 0.8845 0.072 Uiso 1 1 calc R . . H8B H 0.2653 0.2260 0.8793 0.072 Uiso 1 1 calc R . . C9 C 0.3232(3) 0.1316(3) 0.7937(5) 0.0475(13) Uani 1 1 d . . . C10 C 0.3593(2) 0.0133(3) 0.7222(4) 0.0416(12) Uani 1 1 d . . . C11 C 0.3484(3) -0.0309(4) 0.6283(4) 0.0543(15) Uani 1 1 d . . . H11 H 0.3143 -0.0138 0.5589 0.065 Uiso 1 1 calc R . . C12 C 0.3874(3) -0.0985(4) 0.6385(5) 0.0562(15) Uani 1 1 d . . . H12 H 0.3779 -0.1270 0.5747 0.067 Uiso 1 1 calc R . . C13 C 0.4486(3) -0.0843(4) 0.8226(5) 0.074(2) Uani 1 1 d . . . H13 H 0.4838 -0.1018 0.8907 0.088 Uiso 1 1 calc R . . C14 C 0.4113(3) -0.0171(4) 0.8212(5) 0.0679(18) Uani 1 1 d . . . H14 H 0.4210 0.0081 0.8868 0.081 Uiso 1 1 calc R . . C15 C 0.4457(7) 0.1257(8) 0.5720(10) 0.208(7) Uani 1 1 d . . . H15A H 0.4717 0.0859 0.5605 0.312 Uiso 1 1 calc R . . H15B H 0.4049 0.0986 0.5490 0.312 Uiso 1 1 calc R . . H15C H 0.4680 0.1403 0.6486 0.312 Uiso 1 1 calc R . . C16 C 0.1285(3) 0.2025(5) 0.3481(5) 0.088(2) Uani 1 1 d . . . H16A H 0.1448 0.1848 0.3038 0.131 Uiso 1 1 calc R . . H16B H 0.1184 0.2638 0.3375 0.131 Uiso 1 1 calc R . . H16C H 0.0900 0.1698 0.3269 0.131 Uiso 1 1 calc R . . C17 C 0.1801(3) 0.1852(4) 0.4695(5) 0.0628(16) Uani 1 1 d . . . C18 C 0.4994(9) 0.5766(12) 0.0915(14) 0.109(6) Uani 0.50 1 d P . . 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 Cu 0.0525(6) 0.0365(6) 0.0818(8) 0.000 0.0444(6) 0.000 O1 0.092(3) 0.064(3) 0.065(3) -0.020(2) 0.049(3) -0.029(2) O2 0.070(3) 0.058(3) 0.047(2) -0.010(2) 0.021(2) 0.013(2) O3 0.078(3) 0.069(3) 0.073(3) -0.015(2) 0.027(2) -0.007(2) O4 0.068(3) 0.062(3) 0.055(3) -0.003(2) 0.026(2) 0.006(2) O5 0.094(3) 0.101(4) 0.063(3) -0.008(3) 0.040(3) 0.025(3) O6 0.23(2) 0.44(3) 0.071(9) 0.110(15) -0.012(11) -0.14(2) O7 0.176(7) 0.185(7) 0.150(6) 0.053(6) 0.119(6) 0.072(6) N1 0.050(3) 0.037(2) 0.060(3) -0.006(2) 0.031(2) 0.000(2) N2 0.057(3) 0.055(3) 0.047(3) -0.010(2) 0.027(2) -0.012(2) N3 0.059(3) 0.044(3) 0.062(3) -0.008(2) 0.035(2) -0.010(2) N4 0.056(3) 0.046(3) 0.053(3) -0.009(2) 0.029(2) 0.008(2) N5 0.047(3) 0.046(3) 0.047(3) -0.006(2) 0.020(2) 0.005(2) N6 0.051(3) 0.044(3) 0.059(3) -0.005(2) 0.031(2) 0.000(2) C1 0.077(4) 0.054(4) 0.068(4) -0.013(3) 0.052(3) -0.009(3) C2 0.078(4) 0.055(4) 0.051(3) -0.018(3) 0.038(3) -0.015(3) C3 0.044(3) 0.040(3) 0.044(3) -0.003(2) 0.023(3) -0.002(2) C4 0.048(3) 0.052(3) 0.057(3) -0.011(3) 0.034(3) -0.004(3) C5 0.051(3) 0.049(3) 0.052(3) -0.010(3) 0.031(3) -0.001(3) C6 0.048(3) 0.043(3) 0.061(4) -0.008(3) 0.032(3) -0.002(3) C7 0.065(4) 0.043(3) 0.083(4) -0.005(3) 0.049(3) 0.004(3) C8 0.073(4) 0.054(3) 0.061(4) -0.010(3) 0.042(3) 0.002(3) C9 0.050(3) 0.040(3) 0.054(4) -0.010(3) 0.029(3) -0.005(3) C10 0.041(3) 0.032(3) 0.054(3) -0.003(2) 0.027(3) -0.005(2) C11 0.059(3) 0.055(4) 0.042(3) -0.002(3) 0.024(3) 0.009(3) C12 0.069(4) 0.048(3) 0.058(4) -0.004(3) 0.038(3) 0.006(3) C13 0.068(4) 0.064(4) 0.063(4) -0.005(3) 0.019(3) 0.022(3) C14 0.070(4) 0.067(4) 0.047(3) -0.015(3) 0.019(3) 0.019(3) C15 0.35(2) 0.160(11) 0.210(13) 0.107(10) 0.211(14) 0.149(13) C16 0.081(5) 0.114(6) 0.057(4) 0.006(4) 0.031(4) 0.022(4) C17 0.066(4) 0.061(4) 0.058(4) -0.004(3) 0.032(3) -0.005(3) C18 0.108(13) 0.114(14) 0.096(13) 0.047(11) 0.049(11) 0.004(11) _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 Cu N1 2.024(4) . ? Cu N1 2.024(4) 2_656 ? Cu N6 2.025(4) 1_565 ? Cu N6 2.025(5) 2_666 ? O1 C6 1.219(6) . ? O2 C9 1.238(6) . ? O3 H3C 0.8980 . ? O3 H3B 0.9410 . ? O4 C17 1.255(7) . ? O5 C17 1.260(7) . ? O6 C18 1.26(2) . ? O7 C15 1.380(10) . ? O7 H7 0.8200 . ? N1 C1 1.347(7) . ? N1 C5 1.353(7) . ? N2 C6 1.369(7) . ? N2 C3 1.379(6) . ? N2 H2A 0.8600 . ? N3 C6 1.349(7) . ? N3 C7 1.447(7) . ? N3 H3A 0.8600 . ? N4 C9 1.331(6) . ? N4 C8 1.451(7) . ? N4 H4A 0.8600 . ? N5 C10 1.378(6) . ? N5 C9 1.389(6) . ? N5 H5A 0.8600 . ? N6 C12 1.334(7) . ? N6 C13 1.335(7) . ? N6 Cu 2.025(4) 1_545 ? C1 C2 1.372(8) . ? C1 H1 0.9300 . ? C2 C3 1.388(7) . ? C2 H2 0.9300 . ? C3 C4 1.386(7) . ? C4 C5 1.370(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.515(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C14 1.383(7) . ? C10 C11 1.407(7) . ? C11 C12 1.362(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.367(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.531(9) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N1 91.7(2) . 2_656 ? N1 Cu N6 90.43(18) . 1_565 ? N1 Cu N6 176.52(18) 2_656 1_565 ? N1 Cu N6 176.52(18) . 2_666 ? N1 Cu N6 90.43(18) 2_656 2_666 ? N6 Cu N6 87.6(3) 1_565 2_666 ? H3C O3 H3B 98.0 . . ? C15 O7 H7 109.5 . . ? C1 N1 C5 115.4(5) . . ? C1 N1 Cu 121.9(4) . . ? C5 N1 Cu 122.7(4) . . ? C6 N2 C3 127.2(5) . . ? C6 N2 H2A 116.4 . . ? C3 N2 H2A 116.4 . . ? C6 N3 C7 123.0(5) . . ? C6 N3 H3A 118.5 . . ? C7 N3 H3A 118.5 . . ? C9 N4 C8 121.1(5) . . ? C9 N4 H4A 119.4 . . ? C8 N4 H4A 119.4 . . ? C10 N5 C9 127.0(4) . . ? C10 N5 H5A 116.5 . . ? C9 N5 H5A 116.5 . . ? C12 N6 C13 114.9(5) . . ? C12 N6 Cu 124.9(4) . 1_545 ? C13 N6 Cu 120.1(4) . 1_545 ? N1 C1 C2 123.3(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 120.7(5) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? N2 C3 C4 124.7(5) . . ? N2 C3 C2 118.8(5) . . ? C4 C3 C2 116.5(5) . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 124.5(5) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? O1 C6 N3 123.2(6) . . ? O1 C6 N2 123.8(5) . . ? N3 C6 N2 113.0(5) . . ? N3 C7 C8 113.9(5) . . ? N3 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N3 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C7 110.8(5) . . ? N4 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O2 C9 N4 123.3(5) . . ? O2 C9 N5 122.2(5) . . ? N4 C9 N5 114.4(5) . . ? N5 C10 C14 125.3(5) . . ? N5 C10 C11 119.6(5) . . ? C14 C10 C11 115.1(5) . . ? C12 C11 C10 120.4(5) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? N6 C12 C11 124.4(5) . . ? N6 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? N6 C13 C14 125.1(6) . . ? N6 C13 H13 117.5 . . ? C14 C13 H13 117.5 . . ? C13 C14 C10 120.1(6) . . ? C13 C14 H14 119.9 . . ? C10 C14 H14 119.9 . . ? O7 C15 H15A 109.5 . . ? O7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 O5 124.2(6) . . ? O4 C17 C16 117.4(6) . . ? O5 C17 C16 118.4(6) . . ? 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 Cu N1 C1 -59.5(4) 2_656 . . . ? N6 Cu N1 C1 123.3(4) 1_565 . . . ? N6 Cu N1 C1 68(3) 2_666 . . . ? N1 Cu N1 C5 119.2(5) 2_656 . . . ? N6 Cu N1 C5 -58.1(4) 1_565 . . . ? N6 Cu N1 C5 -113(3) 2_666 . . . ? C5 N1 C1 C2 0.0(8) . . . . ? Cu N1 C1 C2 178.8(5) . . . . ? N1 C1 C2 C3 -2.4(9) . . . . ? C6 N2 C3 C4 -21.1(8) . . . . ? C6 N2 C3 C2 159.9(5) . . . . ? C1 C2 C3 N2 -177.6(5) . . . . ? C1 C2 C3 C4 3.4(8) . . . . ? N2 C3 C4 C5 178.9(5) . . . . ? C2 C3 C4 C5 -2.2(8) . . . . ? C1 N1 C5 C4 1.2(8) . . . . ? Cu N1 C5 C4 -177.5(4) . . . . ? C3 C4 C5 N1 -0.1(8) . . . . ? C7 N3 C6 O1 -4.3(8) . . . . ? C7 N3 C6 N2 175.6(5) . . . . ? C3 N2 C6 O1 3.0(9) . . . . ? C3 N2 C6 N3 -176.9(5) . . . . ? C6 N3 C7 C8 -88.1(6) . . . . ? C9 N4 C8 C7 167.1(5) . . . . ? N3 C7 C8 N4 -61.8(7) . . . . ? C8 N4 C9 O2 2.4(9) . . . . ? C8 N4 C9 N5 -176.2(5) . . . . ? C10 N5 C9 O2 0.5(8) . . . . ? C10 N5 C9 N4 179.1(5) . . . . ? C9 N5 C10 C14 1.0(8) . . . . ? C9 N5 C10 C11 -179.4(5) . . . . ? N5 C10 C11 C12 -179.4(5) . . . . ? C14 C10 C11 C12 0.3(8) . . . . ? C13 N6 C12 C11 1.3(9) . . . . ? Cu N6 C12 C11 -176.2(4) 1_545 . . . ? C10 C11 C12 N6 -1.6(9) . . . . ? C12 N6 C13 C14 0.4(10) . . . . ? Cu N6 C13 C14 178.0(6) 1_545 . . . ? N6 C13 C14 C10 -1.7(11) . . . . ? N5 C10 C14 C13 -179.2(6) . . . . ? C11 C10 C14 C13 1.2(9) . . . . ? 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 C4 H4 O1 0.93 2.34 2.877(7) 116.3 . N5 H5A O4 0.86 1.99 2.842(6) 172.5 . N4 H4A O5 0.86 1.96 2.805(7) 169.3 . N3 H3A O5 0.86 2.58 3.195(7) 129.0 . C14 H14 O2 0.93 2.20 2.813(7) 122.4 . C13 H13 O3 0.93 2.40 3.123(8) 134.2 1_545 C12 H12 O2 0.93 2.51 3.336(8) 148.7 6 C1 H1 O3 0.93 2.48 3.100(8) 124.5 2_656 O3 H3B O2 0.94 1.84 2.704(6) 150.8 5_667 N2 H2A O4 0.86 2.01 2.786(6) 150.0 7_556 O3 H3C O6 0.90 1.96 2.794(19) 153.1 1_556 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.650 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.083 ################### data_CuCl2L _database_code_depnum_ccdc_archive 'CCDC 828241' #TrackingRef '- bisurea complexes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H25 Cl Cu0.50 N7 O4' _chemical_formula_weight 458.66 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.966(2) _cell_length_b 10.949(3) _cell_length_c 11.620(3) _cell_angle_alpha 100.988(3) _cell_angle_beta 98.286(3) _cell_angle_gamma 102.071(3) _cell_volume 1074.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 479 _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8674 _exptl_absorpt_correction_T_max 0.8789 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _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 7161 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3730 _reflns_number_gt 2694 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1388P)^2^+17.2382P] 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 3730 _refine_ls_number_parameters 292 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.1528 _refine_ls_R_factor_gt 0.1219 _refine_ls_wR_factor_ref 0.3833 _refine_ls_wR_factor_gt 0.3642 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.552 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu -0.5000 0.5000 0.5000 0.0405(9) Uani 1 2 d S . . Cl Cl 0.2032(7) 0.9008(5) 0.0594(5) 0.0683(15) Uani 1 1 d . . . O1 O 0.2004(14) 0.4887(11) 0.8824(11) 0.052(3) Uani 1 1 d . . . O2 O 0.4207(15) 0.1174(10) 0.7486(10) 0.049(3) Uani 1 1 d . . . O3 O 0.2347(13) 0.3253(13) 0.5546(12) 0.038(3) Uani 0.85 1 d P A 1 C16 C -0.052(4) 0.109(2) 0.647(2) 0.072(9) Uani 0.80 1 d P A 1 N7 N -0.008(7) 0.137(5) 0.575(5) 0.176(5) Uani 0.50 1 d PDU A 1 O3A O 0.248(5) 0.247(4) 0.502(4) 0.012(11) Uani 0.15 1 d PU A 2 C16A C 0.0000 0.0000 0.5000 0.07(2) Uani 0.40 2 d SPD B 2 N7A N 0.018(2) 0.2015(15) 0.5840(16) 0.010(3) Uani 0.50 1 d PU A 2 O4 O 0.075(3) 0.143(2) 0.174(2) 0.134(8) Uani 1 1 d . . . H15 H 0.1069 0.0625 0.1494 0.080 Uiso 1 1 d R . . H16 H 0.0267 0.1861 0.1369 0.080 Uiso 1 1 d R . . N1 N -0.3473(15) 0.4664(12) 0.6295(11) 0.039(3) Uani 1 1 d U . . N2 N -0.0436(15) 0.3608(14) 0.8754(12) 0.045(3) Uani 1 1 d U . . H2 H -0.0903 0.3022 0.9064 0.054 Uiso 1 1 d R . . N3 N 0.1699(15) 0.3364(12) 0.9901(11) 0.037(2) Uani 1 1 d U . . H3 H 0.1048 0.2770 1.0085 0.045 Uiso 1 1 d R . . N4 N 0.3780(16) 0.1550(11) 0.9399(12) 0.043(3) Uani 1 1 d U . . H4 H 0.3429 0.1207 0.9945 0.051 Uiso 1 1 d R . . N5 N 0.3641(17) -0.0495(12) 0.8410(12) 0.045(3) Uani 1 1 d U . . H5 H 0.3184 -0.0707 0.8956 0.054 Uiso 1 1 d R . . N6 N 0.4659(16) -0.3531(12) 0.6148(11) 0.040(3) Uani 1 1 d U . . C1 C -0.3943(18) 0.3658(16) 0.6795(15) 0.042(4) Uani 1 1 d . . . H1 H -0.4968 0.3179 0.6581 0.050 Uiso 1 1 calc R . . C2 C -0.2932(17) 0.3356(15) 0.7598(15) 0.041(4) Uani 1 1 d . . . H2A H -0.3276 0.2670 0.7937 0.050 Uiso 1 1 calc R . . C3 C -0.1406(18) 0.4028(15) 0.7933(13) 0.037(3) Uani 1 1 d . . . C4 C -0.093(2) 0.5078(18) 0.7439(16) 0.052(4) Uani 1 1 d . . . H4A H 0.0090 0.5569 0.7649 0.062 Uiso 1 1 calc R . . C5 C -0.2010(19) 0.5368(16) 0.6630(15) 0.047(4) Uani 1 1 d . . . H5A H -0.1710 0.6076 0.6309 0.056 Uiso 1 1 calc R . . C6 C 0.1175(18) 0.4029(14) 0.9143(13) 0.036(3) Uani 1 1 d . . . C7 C 0.3334(18) 0.3606(14) 1.0417(14) 0.040(4) Uani 1 1 d . . . H7A H 0.3430 0.3309 1.1153 0.048 Uiso 1 1 calc R . . H7B H 0.3781 0.4524 1.0617 0.048 Uiso 1 1 calc R . . C8 C 0.4257(19) 0.2959(15) 0.9600(15) 0.043(4) Uani 1 1 d . . . H8A H 0.4105 0.3202 0.8839 0.051 Uiso 1 1 calc R . . H8B H 0.5355 0.3253 0.9953 0.051 Uiso 1 1 calc R . . C9 C 0.393(2) 0.0801(13) 0.8351(15) 0.042(4) Uani 1 1 d . . . C10 C 0.4004(18) -0.1491(14) 0.7641(13) 0.036(3) Uani 1 1 d . . . C11 C 0.498(2) -0.1274(14) 0.6855(16) 0.047(4) Uani 1 1 d . . . H11A H 0.5436 -0.0442 0.6816 0.057 Uiso 1 1 calc R . . C12 C 0.526(2) -0.2315(16) 0.6122(15) 0.048(4) Uani 1 1 d . . . H12 H 0.5911 -0.2162 0.5581 0.058 Uiso 1 1 calc R . . C13 C 0.373(2) -0.3714(15) 0.6948(14) 0.043(4) Uani 1 1 d . . . H13 H 0.3286 -0.4550 0.6984 0.051 Uiso 1 1 calc R . . C14 C 0.3411(18) -0.2720(13) 0.7709(13) 0.035(3) Uani 1 1 d . . . H14 H 0.2795 -0.2885 0.8267 0.041 Uiso 1 1 calc R . . C15 C 0.171(2) 0.2513(19) 0.6048(15) 0.054(5) Uani 1 1 d . . . C17 C -0.080(2) 0.223(3) 0.482(2) 0.094(9) Uani 1 1 d U . . 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 Cu 0.0517(18) 0.0358(15) 0.0327(14) 0.0011(11) -0.0031(12) 0.0217(13) Cl 0.084(4) 0.067(3) 0.074(3) 0.040(3) 0.040(3) 0.021(3) O1 0.046(7) 0.047(7) 0.064(8) 0.024(6) 0.005(6) 0.003(6) O2 0.083(9) 0.035(6) 0.039(6) 0.020(5) 0.031(6) 0.016(6) O3 0.025(6) 0.043(8) 0.046(7) 0.021(7) 0.004(5) 0.001(6) C16 0.11(2) 0.051(14) 0.050(14) -0.003(11) 0.055(15) -0.007(14) N7 0.169(9) 0.237(9) 0.102(9) -0.106(9) -0.026(8) 0.173(8) O3A 0.00(2) 0.00(2) 0.01(2) -0.032(19) -0.025(18) -0.013(18) C16A 0.00(2) 0.03(3) 0.12(6) -0.01(3) -0.06(3) -0.020(19) N7A 0.019(6) 0.000(6) 0.010(6) -0.001(5) 0.017(5) -0.008(6) O4 0.16(2) 0.108(16) 0.15(2) 0.023(14) 0.020(16) 0.071(16) N1 0.038(6) 0.043(6) 0.037(6) 0.001(5) 0.001(5) 0.021(5) N2 0.036(5) 0.056(6) 0.051(5) 0.038(5) 0.005(5) 0.007(5) N3 0.040(5) 0.037(5) 0.042(5) 0.019(4) 0.010(5) 0.015(4) N4 0.063(6) 0.019(5) 0.048(6) 0.015(4) 0.019(5) 0.002(5) N5 0.061(7) 0.032(6) 0.051(6) 0.011(5) 0.034(6) 0.015(5) N6 0.050(7) 0.034(6) 0.036(6) 0.009(5) 0.005(5) 0.014(5) C1 0.035(8) 0.045(9) 0.055(10) 0.025(8) 0.010(7) 0.020(7) C2 0.032(8) 0.036(8) 0.060(10) 0.024(7) 0.010(7) 0.003(7) C3 0.040(8) 0.039(8) 0.037(8) 0.013(6) 0.015(7) 0.009(7) C4 0.047(10) 0.053(10) 0.057(11) 0.025(9) 0.005(8) 0.004(8) C5 0.040(9) 0.047(10) 0.054(10) 0.024(8) 0.001(8) 0.004(8) C6 0.043(9) 0.031(8) 0.032(7) 0.004(6) 0.003(6) 0.012(7) C7 0.043(9) 0.029(7) 0.043(8) 0.007(6) -0.004(7) 0.009(7) C8 0.045(9) 0.040(9) 0.048(9) 0.010(7) 0.011(7) 0.022(7) C9 0.056(10) 0.020(7) 0.053(10) 0.003(7) 0.018(8) 0.018(7) C10 0.043(8) 0.028(7) 0.038(8) 0.008(6) 0.011(7) 0.009(6) C11 0.051(10) 0.018(7) 0.076(12) 0.010(7) 0.035(9) -0.001(7) C12 0.056(10) 0.047(10) 0.044(9) 0.006(7) 0.026(8) 0.006(8) C13 0.057(10) 0.029(8) 0.043(9) 0.009(7) -0.002(8) 0.020(7) C14 0.043(8) 0.023(7) 0.043(8) 0.015(6) 0.018(7) 0.009(6) C15 0.072(13) 0.056(11) 0.034(9) -0.004(8) 0.004(8) 0.033(10) C17 0.037(11) 0.14(2) 0.093(17) 0.039(17) -0.012(11) 0.012(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 Cu N6 1.991(12) 1_465 ? Cu N6 1.991(12) 2_556 ? Cu N1 2.026(12) . ? Cu N1 2.026(12) 2_466 ? O1 C6 1.222(19) . ? O2 C9 1.193(19) . ? O3 C15 1.19(2) . ? C16 N7 1.04(8) . ? N7 C17 1.71(7) . ? N7 C15 1.76(7) . ? O3A C15 1.46(5) . ? N7A C15 1.33(3) . ? N7A C17 1.46(3) . ? O4 H15 0.9825 . ? O4 H16 0.8396 . ? N1 C5 1.33(2) . ? N1 C1 1.36(2) . ? N2 C6 1.40(2) . ? N2 C3 1.405(19) . ? N2 H2 0.8581 . ? N3 C6 1.339(19) . ? N3 C7 1.450(19) . ? N3 H3 0.8600 . ? N4 C9 1.37(2) . ? N4 C8 1.475(19) . ? N4 H4 0.8600 . ? N5 C10 1.397(18) . ? N5 C9 1.405(19) . ? N5 H5 0.8467 . ? N6 C12 1.34(2) . ? N6 C13 1.35(2) . ? N6 Cu 1.991(12) 1_645 ? C1 C2 1.34(2) . ? C1 H1 0.9300 . ? C2 C3 1.37(2) . ? C2 H2A 0.9300 . ? C3 C4 1.40(2) . ? C4 C5 1.38(2) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C7 C8 1.52(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C14 1.36(2) . ? C10 C11 1.37(2) . ? C11 C12 1.38(2) . ? C11 H11A 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.37(2) . ? C13 H13 0.9300 . ? C14 H14 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 N6 Cu N6 180.000(2) 1_465 2_556 ? N6 Cu N1 90.7(5) 1_465 . ? N6 Cu N1 89.3(5) 2_556 . ? N6 Cu N1 89.3(5) 1_465 2_466 ? N6 Cu N1 90.7(5) 2_556 2_466 ? N1 Cu N1 180.000(2) . 2_466 ? C16 N7 C17 128(4) . . ? C16 N7 C15 119(4) . . ? C17 N7 C15 88(4) . . ? C15 N7A C17 119.5(17) . . ? H15 O4 H16 134.2 . . ? C5 N1 C1 119.6(13) . . ? C5 N1 Cu 121.8(11) . . ? C1 N1 Cu 118.6(10) . . ? C6 N2 C3 128.8(13) . . ? C6 N2 H2 116.1 . . ? C3 N2 H2 115.1 . . ? C6 N3 C7 122.1(14) . . ? C6 N3 H3 119.2 . . ? C7 N3 H3 118.7 . . ? C9 N4 C8 119.4(13) . . ? C9 N4 H4 120.9 . . ? C8 N4 H4 119.7 . . ? C10 N5 C9 126.7(13) . . ? C10 N5 H5 115.8 . . ? C9 N5 H5 117.5 . . ? C12 N6 C13 116.5(13) . . ? C12 N6 Cu 121.8(11) . 1_645 ? C13 N6 Cu 121.5(10) . 1_645 ? C2 C1 N1 120.2(15) . . ? C2 C1 H1 119.9 . . ? N1 C1 H1 119.9 . . ? C1 C2 C3 121.9(15) . . ? C1 C2 H2A 119.0 . . ? C3 C2 H2A 119.0 . . ? C2 C3 C4 117.9(15) . . ? C2 C3 N2 117.3(14) . . ? C4 C3 N2 124.8(14) . . ? C5 C4 C3 118.3(16) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? N1 C5 C4 122.0(15) . . ? N1 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? O1 C6 N3 124.2(14) . . ? O1 C6 N2 124.3(13) . . ? N3 C6 N2 111.5(14) . . ? N3 C7 C8 113.8(13) . . ? N3 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N3 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C7 111.5(14) . . ? N4 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N4 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O2 C9 N4 125.6(13) . . ? O2 C9 N5 123.9(14) . . ? N4 C9 N5 110.4(14) . . ? C14 C10 C11 118.9(14) . . ? C14 C10 N5 118.6(14) . . ? C11 C10 N5 122.5(13) . . ? C10 C11 C12 118.6(14) . . ? C10 C11 H11A 120.7 . . ? C12 C11 H11A 120.7 . . ? N6 C12 C11 123.5(15) . . ? N6 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? N6 C13 C14 122.8(15) . . ? N6 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C10 C14 C13 119.5(14) . . ? C10 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? O3 C15 N7A 125.1(17) . . ? O3 C15 O3A 42.4(19) . . ? N7A C15 O3A 117.6(19) . . ? O3 C15 N7 136(3) . . ? N7A C15 N7 20.0(15) . . ? O3A C15 N7 113(3) . . ? N7A C17 N7 23.1(18) . . ? 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 N6 Cu N1 C5 -78.9(13) 1_465 . . . ? N6 Cu N1 C5 101.1(13) 2_556 . . . ? N1 Cu N1 C5 20(100) 2_466 . . . ? N6 Cu N1 C1 103.9(12) 1_465 . . . ? N6 Cu N1 C1 -76.1(12) 2_556 . . . ? N1 Cu N1 C1 -157(100) 2_466 . . . ? C5 N1 C1 C2 -2(2) . . . . ? Cu N1 C1 C2 175.5(12) . . . . ? N1 C1 C2 C3 -1(3) . . . . ? C1 C2 C3 C4 2(3) . . . . ? C1 C2 C3 N2 -178.2(15) . . . . ? C6 N2 C3 C2 172.6(15) . . . . ? C6 N2 C3 C4 -8(3) . . . . ? C2 C3 C4 C5 -1(3) . . . . ? N2 C3 C4 C5 179.2(16) . . . . ? C1 N1 C5 C4 3(3) . . . . ? Cu N1 C5 C4 -174.5(13) . . . . ? C3 C4 C5 N1 -1(3) . . . . ? C7 N3 C6 O1 0(2) . . . . ? C7 N3 C6 N2 179.1(13) . . . . ? C3 N2 C6 O1 2(3) . . . . ? C3 N2 C6 N3 -177.6(15) . . . . ? C6 N3 C7 C8 -81.8(17) . . . . ? C9 N4 C8 C7 151.7(14) . . . . ? N3 C7 C8 N4 -66.7(17) . . . . ? C8 N4 C9 O2 -12(3) . . . . ? C8 N4 C9 N5 171.1(14) . . . . ? C10 N5 C9 O2 18(3) . . . . ? C10 N5 C9 N4 -165.1(15) . . . . ? C9 N5 C10 C14 -169.3(16) . . . . ? C9 N5 C10 C11 13(3) . . . . ? C14 C10 C11 C12 3(3) . . . . ? N5 C10 C11 C12 -179.5(16) . . . . ? C13 N6 C12 C11 0(3) . . . . ? Cu N6 C12 C11 176.0(14) 1_645 . . . ? C10 C11 C12 N6 -1(3) . . . . ? C12 N6 C13 C14 0(2) . . . . ? Cu N6 C13 C14 -176.7(11) 1_645 . . . ? C11 C10 C14 C13 -4(2) . . . . ? N5 C10 C14 C13 178.8(14) . . . . ? N6 C13 C14 C10 2(2) . . . . ? C17 N7A C15 O3 9(3) . . . . ? C17 N7A C15 O3A -41(3) . . . . ? C17 N7A C15 N7 -122(8) . . . . ? C16 N7 C15 O3 -158(4) . . . . ? C17 N7 C15 O3 -25(3) . . . . ? C16 N7 C15 N7A -94(6) . . . . ? C17 N7 C15 N7A 39(6) . . . . ? C16 N7 C15 O3A 158(4) . . . . ? C17 N7 C15 O3A -69(3) . . . . ? C15 N7A C17 N7 130(7) . . . . ? C16 N7 C17 N7A 95(5) . . . . ? C15 N7 C17 N7A -30(5) . . . . ? 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 H2 Cl 0.86 2.37 3.201(14) 162.4 2_566 C5 H5A O3 0.93 2.44 3.19(2) 138.5 2_566 N4 H4 Cl 0.86 2.76 3.522(13) 147.8 1_546 N5 H5 Cl 0.85 2.33 3.174(14) 172.1 1_546 O4 H15 Cl 0.98 2.27 3.24(2) 166.2 1_545 C13 H13 O3 0.93 2.55 3.29(2) 137.3 1_545 O4 H16 Cl 0.84 2.71 3.29(2) 127.6 2_565 C1 H1 O3 0.93 2.56 3.334(19) 141.5 1_455 C2 H2A O2 0.93 2.42 3.086(19) 129.0 1_455 C12 H12 O3 0.93 2.52 3.28(2) 139.1 2_656 C4 H4A O1 0.93 2.37 2.95(2) 120.1 . C8 H8A O2 0.97 2.49 2.821(19) 99.6 . C11 H11A O2 0.93 2.34 2.893(18) 117.5 . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.010 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.161 ################# data_CoSO4L _database_code_depnum_ccdc_archive 'CCDC 828242' #TrackingRef '- bisurea complexes-R1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H76 Co2 N18 O26 S2' _chemical_formula_weight 1455.2 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' Co Co 0.3494 0.9721 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 11.8981(3) _cell_length_b 16.9246(5) _cell_length_c 19.3535(5) _cell_angle_alpha 90.00 _cell_angle_beta 125.174(2) _cell_angle_gamma 90.00 _cell_volume 3185.61(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8759 _exptl_absorpt_correction_T_max 0.9048 _exptl_absorpt_process_details SADABS _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 'Bruker APEX II area detector' _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 24862 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.42 _reflns_number_total 7147 _reflns_number_gt 4889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1000P)^2^+0.7487P] 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 7147 _refine_ls_number_parameters 474 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1741 _refine_ls_wR_factor_gt 0.1559 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.059 _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 Co Co 0.87359(4) 1.02514(2) 0.25591(2) 0.03997(16) Uani 1 1 d . . . S S 0.53529(10) 0.21943(5) 0.21215(5) 0.0572(3) Uani 1 1 d . . . O1 O 0.5880(3) 0.63468(16) 0.11077(16) 0.0736(8) Uani 1 1 d . . . O2 O 1.2170(3) 0.66607(14) 0.45153(13) 0.0588(7) Uani 1 1 d . . . O3 O 1.0587(2) 0.42397(14) 0.42477(14) 0.0555(6) Uani 1 1 d . . . O4 O 0.7576(3) 1.03701(14) 0.30458(16) 0.0524(6) Uani 1 1 d D . . H4 H 0.7223 0.9944 0.3018 0.079 Uiso 1 1 calc R . . H4A H 0.719(4) 1.0765(19) 0.305(3) 0.080 Uiso 1 1 d D . . O5 O 0.7317(3) 1.10006(14) 0.15440(14) 0.0506(6) Uani 1 1 d D . . H5 H 0.7629 1.1129 0.1278 0.076 Uiso 1 1 calc R . . H5A H 0.679(4) 1.131(2) 0.152(3) 0.080 Uiso 1 1 d D . . O6 O 0.9822(3) 1.02130(19) 0.20008(17) 0.0575(7) Uani 1 1 d . . . O7 O 0.5737(3) 0.21633(18) 0.15283(15) 0.0827(10) Uani 1 1 d . A . O8 O 0.6340(4) 0.1765(2) 0.29107(18) 0.0597(12) Uani 0.745(6) 1 d P A 1 O9 O 0.3959(5) 0.1880(5) 0.1771(3) 0.110(2) Uani 0.745(6) 1 d P A 1 O10 O 0.5378(5) 0.3020(2) 0.2373(2) 0.0885(18) Uani 0.745(6) 1 d P A 1 O8' O 0.4034(10) 0.2512(7) 0.1660(6) 0.059(3) Uani 0.255(6) 1 d P A 2 O9' O 0.6350(11) 0.2530(8) 0.2842(5) 0.074(4) Uani 0.255(6) 1 d P A 2 O10' O 0.5331(18) 0.1339(8) 0.2199(14) 0.121(7) Uani 0.255(6) 1 d P A 2 O11 O 0.3635(4) 0.4278(2) 0.1572(3) 0.0954(11) Uani 1 1 d D . . H11A H 0.410(4) 0.3906(16) 0.189(2) 0.080 Uiso 1 1 d D . . H11B H 0.412(4) 0.4678(15) 0.178(3) 0.080 Uiso 1 1 d D . . O12 O 0.4310(5) 0.0432(2) 0.2833(3) 0.1038(12) Uani 1 1 d D . . H12A H 0.479(4) 0.067(3) 0.272(3) 0.080 Uiso 1 1 d D . . H12B H 0.446(4) 0.064(3) 0.3283(19) 0.080 Uiso 1 1 d D . . O13 O 0.7055(4) 0.3934(3) 0.2141(3) 0.1149(14) Uani 1 1 d D . . H13A H 0.670(4) 0.4381(18) 0.213(2) 0.080 Uiso 1 1 d D . . H13B H 0.773(3) 0.388(2) 0.2660(15) 0.080 Uiso 1 1 d D . . N1 N 0.7501(3) 0.92612(16) 0.17809(14) 0.0436(6) Uani 1 1 d . . . N2 N 0.5380(3) 0.73390(16) 0.01708(15) 0.0491(7) Uani 1 1 d . . . H2 H 0.4937 0.7447 -0.0359 0.059 Uiso 1 1 calc R . . N3 N 0.4673(3) 0.60672(17) -0.02775(19) 0.0615(9) Uani 1 1 d . . . H3 H 0.4412 0.6225 -0.0772 0.074 Uiso 1 1 calc R . . N4 N 1.0085(3) 0.94207(16) 0.35265(14) 0.0443(6) Uani 1 1 d . . . N5 N 1.2469(3) 0.76946(16) 0.53656(14) 0.0475(7) Uani 1 1 d . . . H5' H 1.2870 0.7845 0.5881 0.057 Uiso 1 1 calc R . . N6 N 1.3368(3) 0.64849(16) 0.59288(15) 0.0487(7) Uani 1 1 d . . . H6 H 1.3767 0.6711 0.6414 0.058 Uiso 1 1 calc R . . N7 N 1.2268(3) 0.43787(18) 0.56454(18) 0.0632(9) Uani 1 1 d . . . H7 H 1.2863 0.4134 0.6105 0.076 Uiso 1 1 calc R . . N8 N 1.1714(3) 0.31521(17) 0.50699(16) 0.0536(8) Uani 1 1 d . . . H8 H 1.2328 0.3004 0.5580 0.064 Uiso 1 1 calc R . . N9 N 0.9897(3) 0.12780(17) 0.33351(16) 0.0477(7) Uani 1 1 d . . . C1 C 0.7375(4) 0.8587(2) 0.20825(19) 0.0533(9) Uani 1 1 d . . . H1 H 0.7788 0.8557 0.2661 0.064 Uiso 1 1 calc R . . C2 C 0.6678(4) 0.7926(2) 0.16030(19) 0.0552(9) Uani 1 1 d . . . H2A H 0.6617 0.7473 0.1851 0.066 Uiso 1 1 calc R . . C3 C 0.6065(3) 0.79603(18) 0.07287(17) 0.0408(7) Uani 1 1 d . . . C4 C 0.6128(3) 0.86790(19) 0.04068(18) 0.0461(8) Uani 1 1 d . . . H4' H 0.5680 0.8741 -0.0173 0.055 Uiso 1 1 calc R . . C5 C 0.6839(3) 0.9291(2) 0.09352(18) 0.0471(8) Uani 1 1 d . . . H5B H 0.6874 0.9761 0.0699 0.056 Uiso 1 1 calc R . . C6 C 0.5338(4) 0.6570(2) 0.0376(2) 0.0505(8) Uani 1 1 d . . . C7 C 0.4388(4) 0.5265(2) -0.0167(3) 0.0653(11) Uani 1 1 d . . . H7A H 0.3622 0.5062 -0.0706 0.078 Uiso 1 1 calc R . . H7B H 0.4123 0.5262 0.0222 0.078 Uiso 1 1 calc R . . C8 C 1.0715(3) 0.8848(2) 0.33919(19) 0.0491(8) Uani 1 1 d . . . H8A H 1.0615 0.8849 0.2879 0.059 Uiso 1 1 calc R . . C9 C 1.1495(3) 0.8261(2) 0.39572(19) 0.0479(8) Uani 1 1 d . . . H9 H 1.1897 0.7877 0.3822 0.058 Uiso 1 1 calc R . . C10 C 1.1680(3) 0.82471(18) 0.47367(17) 0.0425(7) Uani 1 1 d . . . C11 C 1.1060(4) 0.8850(2) 0.48897(18) 0.0536(9) Uani 1 1 d . . . H11 H 1.1183 0.8878 0.5409 0.064 Uiso 1 1 calc R . . C12 C 1.0270(4) 0.9402(2) 0.42815(19) 0.0534(9) Uani 1 1 d . . . H12 H 0.9837 0.9785 0.4395 0.064 Uiso 1 1 calc R . . C13 C 1.2656(3) 0.69253(19) 0.52279(18) 0.0436(7) Uani 1 1 d . . . C14 C 1.3482(3) 0.5635(2) 0.5889(2) 0.0509(8) Uani 1 1 d . . . H14A H 1.4257 0.5443 0.6431 0.061 Uiso 1 1 calc R . . H14B H 1.3646 0.5508 0.5465 0.061 Uiso 1 1 calc R . . C15 C 1.2189(4) 0.5233(2) 0.5670(3) 0.0614(10) Uani 1 1 d . . . H15A H 1.2014 0.5377 0.6085 0.074 Uiso 1 1 calc R . . H15B H 1.1422 0.5419 0.5123 0.074 Uiso 1 1 calc R . . C16 C 1.1457(3) 0.3955(2) 0.4941(2) 0.0488(8) Uani 1 1 d . . . C17 C 1.1090(3) 0.25646(19) 0.44679(19) 0.0445(7) Uani 1 1 d . . . C18 C 1.1703(3) 0.1819(2) 0.4670(2) 0.0553(9) Uani 1 1 d . . . H18 H 1.2525 0.1734 0.5195 0.066 Uiso 1 1 calc R . . C19 C 1.1099(3) 0.1214(2) 0.4099(2) 0.0542(9) Uani 1 1 d . . . H19 H 1.1547 0.0729 0.4249 0.065 Uiso 1 1 calc R . . C20 C 0.9332(4) 0.2000(2) 0.3149(2) 0.0567(10) Uani 1 1 d . . . H20 H 0.8509 0.2069 0.2621 0.068 Uiso 1 1 calc R . . C21 C 0.9867(4) 0.2648(2) 0.3674(2) 0.0558(9) Uani 1 1 d . . . H21 H 0.9417 0.3132 0.3499 0.067 Uiso 1 1 calc R . . C22 C 1.0786(6) 1.0817(4) 0.2066(4) 0.110(2) Uani 1 1 d . . . H22A H 1.0274 1.1264 0.1721 0.165 Uiso 1 1 calc R . . H22B H 1.1307 1.0594 0.1877 0.165 Uiso 1 1 calc R . . H22C H 1.1401 1.0983 0.2644 0.165 Uiso 1 1 calc R . . H6A H 0.972(4) 0.989(3) 0.174(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 Co 0.0503(3) 0.0367(2) 0.0269(2) -0.00036(16) 0.01877(18) -0.00006(18) S 0.0660(6) 0.0490(5) 0.0330(4) -0.0023(3) 0.0148(4) 0.0124(4) O1 0.107(2) 0.0488(15) 0.0502(14) -0.0035(12) 0.0364(15) -0.0130(15) O2 0.0838(17) 0.0490(14) 0.0344(11) -0.0097(10) 0.0287(12) 0.0047(12) O3 0.0611(14) 0.0463(13) 0.0491(13) 0.0053(11) 0.0259(11) 0.0014(11) O4 0.0721(16) 0.0397(13) 0.0554(13) 0.0026(11) 0.0425(13) 0.0039(11) O5 0.0673(15) 0.0453(14) 0.0372(11) 0.0074(10) 0.0289(11) 0.0077(11) O6 0.0721(17) 0.0597(17) 0.0502(14) -0.0120(13) 0.0409(13) -0.0128(14) O7 0.115(2) 0.083(2) 0.0393(12) 0.0102(13) 0.0379(15) 0.0410(18) O8 0.079(2) 0.056(3) 0.0306(15) 0.0037(14) 0.0239(15) 0.0196(19) O9 0.073(3) 0.146(6) 0.060(3) -0.017(3) 0.008(2) -0.023(3) O10 0.147(4) 0.049(2) 0.055(2) -0.0001(17) 0.051(3) 0.024(2) O8' 0.048(5) 0.048(6) 0.057(6) -0.017(5) 0.016(4) 0.008(5) O9' 0.062(6) 0.106(12) 0.029(4) -0.018(6) 0.012(4) 0.009(6) O10' 0.142(14) 0.043(7) 0.22(2) 0.036(10) 0.132(16) 0.035(8) O11 0.100(3) 0.075(2) 0.119(3) -0.011(2) 0.068(2) 0.0139(19) O12 0.122(3) 0.089(3) 0.122(3) -0.031(2) 0.083(3) -0.008(2) O13 0.107(3) 0.126(4) 0.094(3) 0.005(3) 0.047(2) 0.012(3) N1 0.0551(15) 0.0387(14) 0.0300(11) -0.0022(10) 0.0205(11) -0.0026(12) N2 0.0600(16) 0.0386(14) 0.0346(12) -0.0041(11) 0.0190(12) -0.0030(12) N3 0.074(2) 0.0421(16) 0.0506(15) -0.0067(13) 0.0256(15) -0.0069(14) N4 0.0531(15) 0.0433(15) 0.0289(11) -0.0027(10) 0.0193(11) 0.0029(12) N5 0.0651(17) 0.0407(15) 0.0257(10) -0.0036(10) 0.0198(11) 0.0080(12) N6 0.0598(16) 0.0390(14) 0.0333(12) -0.0067(11) 0.0188(12) -0.0010(12) N7 0.0733(19) 0.0421(16) 0.0500(16) -0.0048(13) 0.0215(15) -0.0085(15) N8 0.0603(16) 0.0426(15) 0.0373(13) -0.0010(12) 0.0161(12) -0.0071(13) N9 0.0508(15) 0.0456(16) 0.0389(13) -0.0009(12) 0.0213(12) -0.0012(12) C1 0.071(2) 0.050(2) 0.0313(14) -0.0063(14) 0.0247(15) -0.0052(17) C2 0.074(2) 0.0447(19) 0.0374(15) -0.0020(14) 0.0269(16) -0.0111(17) C3 0.0420(15) 0.0406(16) 0.0336(13) -0.0053(12) 0.0181(12) -0.0012(13) C4 0.0530(18) 0.0446(18) 0.0295(13) 0.0001(13) 0.0173(13) -0.0020(14) C5 0.0594(18) 0.0389(17) 0.0319(14) 0.0005(12) 0.0200(14) -0.0022(14) C6 0.0558(19) 0.0418(18) 0.0448(17) -0.0033(14) 0.0237(15) -0.0029(15) C7 0.061(2) 0.048(2) 0.069(2) -0.0124(18) 0.0272(19) -0.0071(16) C8 0.0603(19) 0.056(2) 0.0308(14) 0.0024(14) 0.0261(14) 0.0071(16) C9 0.0613(19) 0.0505(19) 0.0373(15) 0.0012(14) 0.0315(15) 0.0093(15) C10 0.0484(16) 0.0394(17) 0.0284(13) -0.0056(12) 0.0156(12) -0.0019(13) C11 0.074(2) 0.053(2) 0.0270(13) -0.0012(13) 0.0250(15) 0.0136(17) C12 0.072(2) 0.053(2) 0.0329(14) -0.0006(14) 0.0289(15) 0.0162(17) C13 0.0470(16) 0.0425(17) 0.0351(14) -0.0042(13) 0.0200(13) -0.0019(14) C14 0.0579(19) 0.0406(18) 0.0455(16) -0.0035(14) 0.0247(15) 0.0020(15) C15 0.073(2) 0.0427(19) 0.065(2) -0.0124(17) 0.038(2) -0.0061(17) C16 0.0547(19) 0.0427(18) 0.0502(17) -0.0041(14) 0.0309(16) -0.0093(15) C17 0.0487(17) 0.0411(17) 0.0399(14) -0.0012(13) 0.0233(13) -0.0065(14) C18 0.0472(17) 0.048(2) 0.0432(16) 0.0011(15) 0.0104(14) -0.0026(15) C19 0.0474(18) 0.0418(18) 0.0548(19) -0.0005(15) 0.0187(15) 0.0014(14) C20 0.0567(19) 0.0436(19) 0.0407(16) -0.0010(14) 0.0112(15) 0.0007(16) C21 0.0567(19) 0.0411(18) 0.0473(17) -0.0007(15) 0.0170(15) -0.0004(15) C22 0.096(4) 0.152(6) 0.089(4) -0.012(4) 0.058(3) 0.005(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 Co O4 2.081(3) . ? Co O6 2.110(3) . ? Co O5 2.121(2) . ? Co N4 2.144(3) . ? Co N1 2.165(3) . ? Co N9 2.189(3) 1_565 ? S O9' 1.329(9) . ? S O8' 1.391(9) . ? S O10' 1.457(13) . ? S O7 1.461(3) . ? S O8 1.474(3) . ? S O10 1.475(4) . ? S O9 1.482(5) . ? O1 C6 1.229(4) . ? O2 C13 1.232(4) . ? O3 C16 1.226(4) . ? O4 H4 0.8200 . ? O4 H4A 0.819(19) . ? O5 H5 0.8200 . ? O5 H5A 0.793(19) . ? O6 C22 1.486(7) . ? O6 H6A 0.70(4) . ? O11 H11A 0.828(18) . ? O11 H11B 0.828(18) . ? O12 H12A 0.824(18) . ? O12 H12B 0.855(18) . ? O13 H13A 0.858(18) . ? O13 H13B 0.855(18) . ? N1 C1 1.329(4) . ? N1 C5 1.348(4) . ? N2 C6 1.370(4) . ? N2 C3 1.386(4) . ? N2 H2 0.8600 . ? N3 C6 1.341(4) . ? N3 C7 1.445(5) . ? N3 H3 0.8600 . ? N4 C8 1.339(4) . ? N4 C12 1.347(4) . ? N5 C13 1.373(4) . ? N5 C10 1.386(4) . ? N5 H5' 0.8600 . ? N6 C13 1.338(4) . ? N6 C14 1.451(4) . ? N6 H6 0.8600 . ? N7 C16 1.338(4) . ? N7 C15 1.451(5) . ? N7 H7 0.8600 . ? N8 C17 1.379(4) . ? N8 C16 1.383(4) . ? N8 H8 0.8600 . ? N9 C20 1.340(4) . ? N9 C19 1.344(4) . ? N9 Co 2.189(3) 1_545 ? C1 C2 1.383(5) . ? C1 H1 0.9300 . ? C2 C3 1.406(4) . ? C2 H2A 0.9300 . ? C3 C4 1.388(4) . ? C4 C5 1.356(4) . ? C4 H4' 0.9300 . ? C5 H5B 0.9300 . ? C7 C7 1.503(8) 3_665 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.369(4) . ? C8 H8A 0.9300 . ? C9 C10 1.393(4) . ? C9 H9 0.9300 . ? C10 C11 1.387(5) . ? C11 C12 1.366(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C14 C15 1.503(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 C21 1.387(4) . ? C17 C18 1.396(5) . ? C18 C19 1.368(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.375(5) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 Co O6 175.22(10) . . ? O4 Co O5 88.84(10) . . ? O6 Co O5 86.55(11) . . ? O4 Co N4 91.49(10) . . ? O6 Co N4 93.20(11) . . ? O5 Co N4 175.74(10) . . ? O4 Co N1 91.61(10) . . ? O6 Co N1 89.46(11) . . ? O5 Co N1 87.66(10) . . ? N4 Co N1 88.08(10) . . ? O4 Co N9 86.20(11) . 1_565 ? O6 Co N9 92.59(12) . 1_565 ? O5 Co N9 90.69(10) . 1_565 ? N4 Co N9 93.57(10) . 1_565 ? N1 Co N9 177.29(10) . 1_565 ? O9' S O8' 120.2(7) . . ? O9' S O10' 112.0(10) . . ? O8' S O10' 111.7(8) . . ? O9' S O7 110.2(5) . . ? O8' S O7 104.9(5) . . ? O10' S O7 94.5(7) . . ? O9' S O8 55.0(6) . . ? O8' S O8 141.9(6) . . ? O10' S O8 57.0(8) . . ? O7 S O8 111.94(19) . . ? O9' S O10 54.0(6) . . ? O8' S O10 69.3(5) . . ? O10' S O10 154.9(8) . . ? O7 S O10 109.7(2) . . ? O8 S O10 105.8(2) . . ? O9' S O9 136.1(6) . . ? O8' S O9 45.1(5) . . ? O10' S O9 67.0(7) . . ? O7 S O9 113.6(2) . . ? O8 S O9 108.1(3) . . ? O10 S O9 107.2(4) . . ? Co O4 H4 109.5 . . ? Co O4 H4A 128(3) . . ? H4 O4 H4A 116.4 . . ? Co O5 H5 109.5 . . ? Co O5 H5A 129(3) . . ? H5 O5 H5A 114.3 . . ? C22 O6 Co 127.3(3) . . ? C22 O6 H6A 114(4) . . ? Co O6 H6A 118(4) . . ? H11A O11 H11B 106(3) . . ? H12A O12 H12B 108(3) . . ? H13A O13 H13B 104(3) . . ? C1 N1 C5 115.5(3) . . ? C1 N1 Co 124.22(19) . . ? C5 N1 Co 120.2(2) . . ? C6 N2 C3 126.7(3) . . ? C6 N2 H2 116.7 . . ? C3 N2 H2 116.7 . . ? C6 N3 C7 121.2(3) . . ? C6 N3 H3 119.4 . . ? C7 N3 H3 119.4 . . ? C8 N4 C12 115.7(3) . . ? C8 N4 Co 121.7(2) . . ? C12 N4 Co 122.4(2) . . ? C13 N5 C10 125.0(2) . . ? C13 N5 H5' 117.5 . . ? C10 N5 H5' 117.5 . . ? C13 N6 C14 121.5(3) . . ? C13 N6 H6 119.2 . . ? C14 N6 H6 119.2 . . ? C16 N7 C15 123.1(3) . . ? C16 N7 H7 118.5 . . ? C15 N7 H7 118.5 . . ? C17 N8 C16 126.9(3) . . ? C17 N8 H8 116.6 . . ? C16 N8 H8 116.6 . . ? C20 N9 C19 114.8(3) . . ? C20 N9 Co 121.3(2) . 1_545 ? C19 N9 Co 122.8(2) . 1_545 ? N1 C1 C2 125.1(3) . . ? N1 C1 H1 117.4 . . ? C2 C1 H1 117.4 . . ? C1 C2 C3 118.0(3) . . ? C1 C2 H2A 121.0 . . ? C3 C2 H2A 121.0 . . ? N2 C3 C4 118.3(3) . . ? N2 C3 C2 124.8(3) . . ? C4 C3 C2 116.8(3) . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4' 119.9 . . ? C3 C4 H4' 119.9 . . ? N1 C5 C4 124.1(3) . . ? N1 C5 H5B 117.9 . . ? C4 C5 H5B 117.9 . . ? O1 C6 N3 121.6(3) . . ? O1 C6 N2 123.0(3) . . ? N3 C6 N2 115.4(3) . . ? N3 C7 C7 111.9(4) . 3_665 ? N3 C7 H7A 109.2 . . ? C7 C7 H7A 109.2 3_665 . ? N3 C7 H7B 109.2 . . ? C7 C7 H7B 109.2 3_665 . ? H7A C7 H7B 107.9 . . ? N4 C8 C9 124.6(3) . . ? N4 C8 H8A 117.7 . . ? C9 C8 H8A 117.7 . . ? C8 C9 C10 119.3(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N5 C10 C11 118.9(3) . . ? N5 C10 C9 124.6(3) . . ? C11 C10 C9 116.5(3) . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? N4 C12 C11 123.5(3) . . ? N4 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? O2 C13 N6 123.2(3) . . ? O2 C13 N5 122.5(3) . . ? N6 C13 N5 114.2(3) . . ? N6 C14 C15 110.6(3) . . ? N6 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N6 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N7 C15 C14 112.7(3) . . ? N7 C15 H15A 109.1 . . ? C14 C15 H15A 109.1 . . ? N7 C15 H15B 109.1 . . ? C14 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? O3 C16 N7 124.2(3) . . ? O3 C16 N8 122.9(3) . . ? N7 C16 N8 112.8(3) . . ? N8 C17 C21 125.0(3) . . ? N8 C17 C18 118.3(3) . . ? C21 C17 C18 116.6(3) . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? N9 C19 C18 124.0(3) . . ? N9 C19 H19 118.0 . . ? C18 C19 H19 118.0 . . ? N9 C20 C21 125.6(3) . . ? N9 C20 H20 117.2 . . ? C21 C20 H20 117.2 . . ? C20 C21 C17 118.8(3) . . ? C20 C21 H21 120.6 . . ? C17 C21 H21 120.6 . . ? O6 C22 H22A 109.5 . . ? O6 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O6 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 O4 Co O6 C22 65.1(14) . . . . ? O5 Co O6 C22 80.4(4) . . . . ? N4 Co O6 C22 -103.8(4) . . . . ? N1 Co O6 C22 168.1(4) . . . . ? N9 Co O6 C22 -10.1(4) 1_565 . . . ? O4 Co N1 C1 -60.8(3) . . . . ? O6 Co N1 C1 123.9(3) . . . . ? O5 Co N1 C1 -149.5(3) . . . . ? N4 Co N1 C1 30.7(3) . . . . ? N9 Co N1 C1 -97(2) 1_565 . . . ? O4 Co N1 C5 121.9(3) . . . . ? O6 Co N1 C5 -53.4(3) . . . . ? O5 Co N1 C5 33.1(3) . . . . ? N4 Co N1 C5 -146.7(3) . . . . ? N9 Co N1 C5 86(2) 1_565 . . . ? O4 Co N4 C8 149.9(3) . . . . ? O6 Co N4 C8 -31.0(3) . . . . ? O5 Co N4 C8 55.5(15) . . . . ? N1 Co N4 C8 58.3(3) . . . . ? N9 Co N4 C8 -123.8(3) 1_565 . . . ? O4 Co N4 C12 -24.9(3) . . . . ? O6 Co N4 C12 154.2(3) . . . . ? O5 Co N4 C12 -119.3(14) . . . . ? N1 Co N4 C12 -116.4(3) . . . . ? N9 Co N4 C12 61.4(3) 1_565 . . . ? C5 N1 C1 C2 2.7(6) . . . . ? Co N1 C1 C2 -174.8(3) . . . . ? N1 C1 C2 C3 0.8(6) . . . . ? C6 N2 C3 C4 172.3(3) . . . . ? C6 N2 C3 C2 -9.4(6) . . . . ? C1 C2 C3 N2 177.3(3) . . . . ? C1 C2 C3 C4 -4.4(5) . . . . ? N2 C3 C4 C5 -177.0(3) . . . . ? C2 C3 C4 C5 4.6(5) . . . . ? C1 N1 C5 C4 -2.5(5) . . . . ? Co N1 C5 C4 175.0(3) . . . . ? C3 C4 C5 N1 -1.1(6) . . . . ? C7 N3 C6 O1 9.2(6) . . . . ? C7 N3 C6 N2 -171.5(3) . . . . ? C3 N2 C6 O1 3.2(6) . . . . ? C3 N2 C6 N3 -176.1(3) . . . . ? C6 N3 C7 C7 -81.3(6) . . . 3_665 ? C12 N4 C8 C9 0.8(5) . . . . ? Co N4 C8 C9 -174.3(3) . . . . ? N4 C8 C9 C10 -0.8(6) . . . . ? C13 N5 C10 C11 151.1(4) . . . . ? C13 N5 C10 C9 -31.2(5) . . . . ? C8 C9 C10 N5 -178.6(3) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? N5 C10 C11 C12 -179.6(3) . . . . ? C9 C10 C11 C12 2.5(5) . . . . ? C8 N4 C12 C11 1.0(5) . . . . ? Co N4 C12 C11 176.0(3) . . . . ? C10 C11 C12 N4 -2.6(6) . . . . ? C14 N6 C13 O2 -7.3(5) . . . . ? C14 N6 C13 N5 170.4(3) . . . . ? C10 N5 C13 O2 2.9(6) . . . . ? C10 N5 C13 N6 -174.9(3) . . . . ? C13 N6 C14 C15 -78.1(4) . . . . ? C16 N7 C15 C14 -116.0(4) . . . . ? N6 C14 C15 N7 -178.4(3) . . . . ? C15 N7 C16 O3 1.0(6) . . . . ? C15 N7 C16 N8 -179.8(3) . . . . ? C17 N8 C16 O3 1.7(6) . . . . ? C17 N8 C16 N7 -177.6(3) . . . . ? C16 N8 C17 C21 -17.1(6) . . . . ? C16 N8 C17 C18 164.6(4) . . . . ? N8 C17 C18 C19 178.3(3) . . . . ? C21 C17 C18 C19 -0.1(6) . . . . ? C20 N9 C19 C18 2.3(6) . . . . ? Co N9 C19 C18 -165.8(3) 1_545 . . . ? C17 C18 C19 N9 -1.7(6) . . . . ? C19 N9 C20 C21 -1.3(6) . . . . ? Co N9 C20 C21 167.0(3) 1_545 . . . ? N9 C20 C21 C17 -0.3(7) . . . . ? N8 C17 C21 C20 -177.3(4) . . . . ? C18 C17 C21 C20 1.0(6) . . . . ? 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 C20 H20 O5 0.93 2.49 3.112(4) 124.0 1_545 O12 H12B O1 0.855(18) 1.88(3) 2.680(5) 154(5) 2_645 N8 H8 O9 0.86 1.99 2.801(5) 156.4 4_666 N7 H7 O9 0.86 2.09 2.878(7) 152.0 4_666 O5 H5A O7 0.793(19) 1.92(2) 2.709(4) 172(5) 1_565 N6 H6 O10 0.86 2.00 2.843(4) 166.0 3_766 N5 H5' O8 0.86 2.06 2.920(4) 174.8 3_766 O5 H5 O2 0.82 1.91 2.696(3) 160.5 2_755 O6 H6A O3 0.70(4) 2.06(4) 2.727(4) 161(5) 2_755 C22 H22A O2 0.96 2.57 3.373(6) 141.1 2_755 O4 H4A O8 0.819(19) 1.91(2) 2.714(4) 168(5) 1_565 O4 H4 O11 0.82 1.97 2.696(4) 147.3 2_655 O11 H11B O12 0.828(18) 2.02(3) 2.807(6) 158(5) 2_655 O13 H13A O12 0.858(18) 2.17(2) 3.027(6) 173(5) 2_655 N2 H2 O7 0.86 2.03 2.873(4) 167.5 3_665 N3 H3 O13 0.86 2.19 2.948(5) 146.2 3_665 O11 H11A O10 0.828(18) 1.95(3) 2.745(5) 161(5) . O12 H12A O8 0.824(18) 2.49(3) 3.245(6) 153(4) . O12 H12A O9 0.824(18) 2.54(5) 3.068(9) 123(4) . C2 H2A O1 0.93 2.24 2.813(4) 119.2 . C5 H5B O5 0.93 2.52 3.051(4) 116.4 . C9 H9 O2 0.93 2.37 2.855(4) 111.9 . C15 H15B O3 0.97 2.43 2.827(4) 104.1 . C21 H21 O3 0.93 2.29 2.852(4) 118.7 . _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.750 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.069 ###############END