# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Biao Wu' _publ_contact_author_address ; Middle Tianshui Road 18 Lanzhou Gansu China 730000 ; _publ_contact_author_email wubiao@lzb.ac.cn loop_ _publ_author_name 'Biao Wu' 'Yongjing Hao' 'Xiaojuan Huang' 'Chuandong Jia' ; Shaoguang Li ; 'Xiao-Juan Yang' ################ data_CuSO4L _database_code_depnum_ccdc_archive 'CCDC 761485' #TrackingRef '- bisurea complexes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Cu N6 O10 S' _chemical_formula_weight 531.99 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' S S 0.1246 0.1234 '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 Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 18.861(5) _cell_length_b 16.141(4) _cell_length_c 13.487(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4106.0(18) _cell_formula_units_Z 8 _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 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 1.233 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6382 _exptl_absorpt_correction_T_max 0.7905 _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 22679 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.62 _reflns_number_total 4299 _reflns_number_gt 2552 _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^)+(0.0641P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4299 _refine_ls_number_parameters 314 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.048 _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 0.26884(2) 0.76048(3) 0.57260(3) 0.03395(19) Uani 1 1 d . . . S1 S 0.38108(7) 0.7500 0.7500 0.0316(4) Uani 1 2 d S . . S2 S 0.15844(7) 0.7500 0.7500 0.0344(4) Uani 1 2 d S . . O1 O 0.2157(2) 0.8985(3) 0.5697(4) 0.0802(13) Uani 1 1 d D . . H1A H 0.212(3) 0.9491(16) 0.553(4) 0.080 Uiso 1 1 d D . . H1B H 0.179(2) 0.896(3) 0.607(4) 0.080 Uiso 1 1 d D . . O2 O 0.3261(2) 0.6122(3) 0.5652(3) 0.0732(12) Uani 1 1 d D . . H2C H 0.356(2) 0.606(3) 0.515(3) 0.080 Uiso 1 1 d D . . H2B H 0.353(2) 0.618(3) 0.619(3) 0.080 Uiso 1 1 d D . . O3 O 0.33596(13) 0.79606(17) 0.67831(19) 0.0333(7) Uani 1 1 d . . . O4 O 0.42461(15) 0.8101(2) 0.8024(2) 0.0479(8) Uani 1 1 d . . . O5 O 0.20413(13) 0.71231(18) 0.67227(19) 0.0359(7) Uani 1 1 d . . . O6 O 0.11539(14) 0.8155(2) 0.7069(2) 0.0522(9) Uani 1 1 d . . . O7 O 0.39954(15) 0.90945(19) 0.1190(2) 0.0421(8) Uani 1 1 d . . . O8 O 0.14172(15) 0.58066(19) 0.1305(2) 0.0456(8) Uani 1 1 d . . . O9 O 0.1633(2) 0.9527(3) 0.8534(4) 0.0943(14) Uani 1 1 d D . . H9C H 0.198(2) 0.921(3) 0.825(4) 0.080 Uiso 1 1 d D . . H9B H 0.190(2) 0.995(2) 0.881(4) 0.080 Uiso 1 1 d D . . O10 O 0.1226(2) 1.0299(3) 0.6771(4) 0.0869(13) Uani 1 1 d D . . H10A H 0.1612(19) 1.058(3) 0.675(4) 0.080 Uiso 1 1 d D . . H10B H 0.135(3) 1.019(4) 0.737(2) 0.080 Uiso 1 1 d D . . N1 N 0.33685(16) 0.8008(2) 0.4696(2) 0.0309(8) Uani 1 1 d . . . N2 N 0.47593(18) 0.8696(2) 0.2430(2) 0.0347(9) Uani 1 1 d . . . H2A H 0.5200 0.8624 0.2566 0.042 Uiso 1 1 calc R . . N3 N 0.51821(18) 0.9204(2) 0.0971(3) 0.0429(10) Uani 1 1 d . . . H3 H 0.5596 0.9115 0.1216 0.052 Uiso 1 1 calc R . . N4 N 0.20367(17) 0.7176(2) 0.4664(2) 0.0336(8) Uani 1 1 d . . . N5 N 0.06447(18) 0.6250(2) 0.2513(2) 0.0349(9) Uani 1 1 d . . . H5A H 0.0202 0.6306 0.2650 0.042 Uiso 1 1 calc R . . N6 N 0.02415(17) 0.5593(2) 0.1121(2) 0.0383(9) Uani 1 1 d . . . H6 H -0.0177 0.5649 0.1366 0.046 Uiso 1 1 calc R . . C1 C 0.4062(2) 0.7816(3) 0.4710(3) 0.0346(10) Uani 1 1 d . . . H1 H 0.4239 0.7522 0.5248 0.042 Uiso 1 1 calc R . . C2 C 0.4517(2) 0.8032(3) 0.3968(3) 0.0324(10) Uani 1 1 d . . . H2 H 0.4991 0.7878 0.4007 0.039 Uiso 1 1 calc R . . C3 C 0.4280(2) 0.8480(2) 0.3161(3) 0.0286(9) Uani 1 1 d . . . C4 C 0.3563(2) 0.8709(3) 0.3151(3) 0.0365(10) Uani 1 1 d . . . H4 H 0.3379 0.9030 0.2639 0.044 Uiso 1 1 calc R . . C5 C 0.3140(2) 0.8449(3) 0.3921(3) 0.0378(11) Uani 1 1 d . . . H5 H 0.2662 0.8589 0.3900 0.045 Uiso 1 1 calc R . . C6 C 0.4606(2) 0.9017(2) 0.1505(3) 0.0326(10) Uani 1 1 d . . . C7 C 0.5119(2) 0.9556(3) -0.0014(3) 0.0396(11) Uani 1 1 d . . . H7A H 0.4781 0.9234 -0.0395 0.048 Uiso 1 1 calc R . . H7B H 0.5574 0.9523 -0.0347 0.048 Uiso 1 1 calc R . . C8 C 0.2264(2) 0.6682(3) 0.3947(3) 0.0431(12) Uani 1 1 d . . . H8A H 0.2746 0.6557 0.3934 0.052 Uiso 1 1 calc R . . C9 C 0.1843(2) 0.6339(3) 0.3215(3) 0.0411(11) Uani 1 1 d . . . H9A H 0.2031 0.5977 0.2747 0.049 Uiso 1 1 calc R . . C10 C 0.1124(2) 0.6553(3) 0.3201(3) 0.0298(9) Uani 1 1 d . . . C11 C 0.0888(2) 0.7078(2) 0.3943(3) 0.0309(9) Uani 1 1 d . . . H11A H 0.0414 0.7238 0.3956 0.037 Uiso 1 1 calc R . . C12 C 0.1338(2) 0.7365(3) 0.4654(3) 0.0332(10) Uani 1 1 d . . . H12A H 0.1158 0.7703 0.5152 0.040 Uiso 1 1 calc R . . C13 C 0.0812(2) 0.5863(3) 0.1625(3) 0.0335(10) Uani 1 1 d . . . C14 C 0.0341(2) 0.5202(3) 0.0153(3) 0.0385(11) Uani 1 1 d . . . H14A H 0.0715 0.4791 0.0192 0.046 Uiso 1 1 calc R . . H14B H 0.0477 0.5616 -0.0332 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0205(3) 0.0634(4) 0.0180(3) -0.0002(2) -0.0003(2) -0.0070(2) S1 0.0164(7) 0.0579(11) 0.0206(7) -0.0009(7) 0.000 0.000 S2 0.0162(7) 0.0673(12) 0.0198(7) -0.0027(7) 0.000 0.000 O1 0.057(3) 0.096(3) 0.087(3) -0.014(3) 0.021(2) 0.010(3) O2 0.070(3) 0.100(3) 0.050(3) -0.002(2) 0.0023(19) 0.004(2) O3 0.0247(15) 0.0511(19) 0.0242(15) 0.0001(13) -0.0060(12) -0.0028(13) O4 0.0300(16) 0.078(2) 0.0361(18) 0.0014(16) -0.0098(14) -0.0170(16) O5 0.0234(14) 0.062(2) 0.0228(15) -0.0047(14) 0.0051(12) -0.0057(14) O6 0.0290(17) 0.093(3) 0.0349(18) -0.0003(18) -0.0085(14) 0.0190(17) O7 0.0358(18) 0.064(2) 0.0264(16) 0.0078(15) 0.0012(13) -0.0060(15) O8 0.0291(17) 0.066(2) 0.0413(19) -0.0166(16) -0.0014(14) -0.0034(15) O9 0.081(3) 0.081(4) 0.121(4) -0.018(3) -0.004(3) 0.007(2) O10 0.083(3) 0.095(4) 0.082(3) -0.018(3) -0.012(3) -0.007(3) N1 0.0211(17) 0.051(2) 0.0202(17) 0.0018(16) 0.0002(14) -0.0016(16) N2 0.0219(18) 0.054(2) 0.029(2) 0.0064(16) 0.0039(15) 0.0008(16) N3 0.034(2) 0.055(2) 0.040(2) 0.0161(18) 0.0125(17) 0.0029(17) N4 0.0216(17) 0.058(2) 0.0214(17) -0.0042(16) 0.0017(14) -0.0012(17) N5 0.0232(18) 0.053(2) 0.0282(19) -0.0069(17) -0.0020(15) -0.0057(16) N6 0.0257(19) 0.055(2) 0.035(2) -0.0128(18) -0.0049(16) -0.0018(16) C1 0.021(2) 0.054(3) 0.029(2) 0.001(2) -0.0025(18) 0.000(2) C2 0.020(2) 0.046(3) 0.031(2) 0.0006(19) -0.0030(17) -0.0005(18) C3 0.021(2) 0.040(2) 0.025(2) -0.0071(18) 0.0039(17) -0.0048(18) C4 0.032(2) 0.052(3) 0.026(2) 0.009(2) 0.0011(19) 0.005(2) C5 0.020(2) 0.063(3) 0.030(2) 0.005(2) 0.0023(18) 0.004(2) C6 0.037(2) 0.031(2) 0.030(2) 0.0007(18) 0.002(2) 0.0000(19) C7 0.040(2) 0.043(3) 0.037(2) 0.002(2) 0.020(2) 0.002(2) C8 0.022(2) 0.076(3) 0.031(2) -0.010(2) -0.0021(19) 0.006(2) C9 0.031(2) 0.056(3) 0.036(3) -0.015(2) -0.001(2) 0.004(2) C10 0.031(2) 0.036(2) 0.023(2) 0.0041(18) -0.0018(17) -0.0080(18) C11 0.023(2) 0.042(3) 0.028(2) -0.0016(19) -0.0009(17) -0.0010(18) C12 0.025(2) 0.048(3) 0.026(2) -0.0009(19) 0.0036(18) 0.0002(19) C13 0.036(2) 0.035(2) 0.030(2) -0.0012(19) -0.006(2) -0.0023(19) C14 0.037(3) 0.043(3) 0.035(3) -0.010(2) -0.010(2) -0.001(2) _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 O5 1.975(3) . ? Cu O3 1.991(3) . ? Cu N1 1.999(3) . ? Cu N4 2.010(3) . ? Cu O1 2.443(5) . ? Cu O2 2.627(5) . ? S1 O4 1.454(3) . ? S1 O4 1.454(3) 4_566 ? S1 O3 1.487(3) . ? S1 O3 1.487(3) 4_566 ? S2 O6 1.454(3) . ? S2 O6 1.454(3) 4_566 ? S2 O5 1.487(3) 4_566 ? S2 O5 1.487(3) 4_566 ? S2 O5 1.487(3) . ? O1 H1A 0.85(2) . ? O1 H1B 0.853(19) . ? O2 H2C 0.892(19) . ? O2 H2B 0.888(19) . ? O7 C6 1.233(5) . ? O8 C13 1.224(5) . ? O9 H9C 0.91(2) . ? O9 H9B 0.931(19) . ? O10 H10A 0.861(19) . ? O10 H10B 0.855(19) . ? N1 C5 1.337(5) . ? N1 C1 1.344(5) . ? N2 C6 1.381(5) . ? N2 C3 1.383(5) . ? N2 H2A 0.8600 . ? N3 C6 1.338(5) . ? N3 C7 1.450(5) . ? N3 H3 0.8600 . ? N4 C8 1.325(5) . ? N4 C12 1.353(5) . ? N5 C10 1.385(5) . ? N5 C13 1.388(5) . ? N5 H5A 0.8600 . ? N6 C13 1.344(5) . ? N6 C14 1.462(5) . ? N6 H6 0.8600 . ? C1 C2 1.363(5) . ? C1 H1 0.9300 . ? C2 C3 1.381(5) . ? C2 H2 0.9300 . ? C3 C4 1.402(5) . ? C4 C5 1.375(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C7 1.501(8) 5_675 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.383(6) . ? C8 H8A 0.9300 . ? C9 C10 1.399(5) . ? C9 H9A 0.9300 . ? C10 C11 1.384(5) . ? C11 C12 1.361(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C14 C14 1.501(7) 5_565 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 O5 Cu O3 91.09(11) . . ? O5 Cu N1 175.77(13) . . ? O3 Cu N1 89.76(12) . . ? O5 Cu N4 88.36(12) . . ? O3 Cu N4 176.49(13) . . ? N1 Cu N4 90.54(13) . . ? O5 Cu O1 96.68(13) . . ? O3 Cu O1 90.53(14) . . ? N1 Cu O1 87.46(14) . . ? N4 Cu O1 92.98(15) . . ? O5 Cu O2 85.47(12) . . ? O3 Cu O2 91.63(12) . . ? N1 Cu O2 90.36(13) . . ? N4 Cu O2 84.87(13) . . ? O1 Cu O2 176.92(14) . . ? O4 S1 O4 111.3(3) . 4_566 ? O4 S1 O3 107.77(17) . . ? O4 S1 O3 109.94(15) 4_566 . ? O4 S1 O3 109.94(15) . 4_566 ? O4 S1 O3 107.77(17) 4_566 4_566 ? O3 S1 O3 110.2(2) . 4_566 ? O6 S2 O6 112.1(3) . 4_566 ? O6 S2 O5 107.93(17) . 4_566 ? O6 S2 O5 109.84(16) 4_566 4_566 ? O6 S2 O5 107.93(17) . 4_566 ? O6 S2 O5 109.84(16) 4_566 4_566 ? O5 S2 O5 0.0(2) 4_566 4_566 ? O6 S2 O5 109.84(16) . . ? O6 S2 O5 107.93(17) 4_566 . ? O5 S2 O5 109.2(2) 4_566 . ? O5 S2 O5 109.2(2) 4_566 . ? Cu O1 H1A 157(4) . . ? Cu O1 H1B 106(4) . . ? H1A O1 H1B 97(5) . . ? Cu O2 H2C 114(4) . . ? Cu O2 H2B 96(4) . . ? H2C O2 H2B 106(5) . . ? S1 O3 Cu 133.24(18) . . ? S2 O5 Cu 132.59(19) . . ? H9C O9 H9B 101(5) . . ? H10A O10 H10B 85(5) . . ? C5 N1 C1 116.6(3) . . ? C5 N1 Cu 120.6(3) . . ? C1 N1 Cu 122.7(3) . . ? C6 N2 C3 127.0(3) . . ? C6 N2 H2A 116.5 . . ? C3 N2 H2A 116.5 . . ? C6 N3 C7 121.0(4) . . ? C6 N3 H3 119.5 . . ? C7 N3 H3 119.5 . . ? C8 N4 C12 116.4(3) . . ? C8 N4 Cu 122.0(3) . . ? C12 N4 Cu 121.7(3) . . ? C10 N5 C13 126.1(3) . . ? C10 N5 H5A 116.9 . . ? C13 N5 H5A 116.9 . . ? C13 N6 C14 119.2(3) . . ? C13 N6 H6 120.4 . . ? C14 N6 H6 120.4 . . ? N1 C1 C2 122.9(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 120.6(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 N2 118.9(4) . . ? C2 C3 C4 117.2(4) . . ? N2 C3 C4 123.9(4) . . ? C5 C4 C3 118.2(4) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 124.4(4) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? O7 C6 N3 123.4(4) . . ? O7 C6 N2 123.0(4) . . ? N3 C6 N2 113.6(4) . . ? N3 C7 C7 112.0(4) . 5_675 ? N3 C7 H7A 109.2 . . ? C7 C7 H7A 109.2 5_675 . ? N3 C7 H7B 109.2 . . ? C7 C7 H7B 109.2 5_675 . ? H7A C7 H7B 107.9 . . ? N4 C8 C9 125.2(4) . . ? N4 C8 H8A 117.4 . . ? C9 C8 H8A 117.4 . . ? C8 C9 C10 117.9(4) . . ? C8 C9 H9A 121.1 . . ? C10 C9 H9A 121.1 . . ? C11 C10 N5 119.4(4) . . ? C11 C10 C9 116.9(4) . . ? N5 C10 C9 123.6(4) . . ? C12 C11 C10 121.1(4) . . ? C12 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? N4 C12 C11 122.5(4) . . ? N4 C12 H12A 118.7 . . ? C11 C12 H12A 118.7 . . ? O8 C13 N6 123.0(4) . . ? O8 C13 N5 123.4(4) . . ? N6 C13 N5 113.6(4) . . ? N6 C14 C14 108.9(4) . 5_565 ? N6 C14 H14A 109.9 . . ? C14 C14 H14A 109.9 5_565 . ? N6 C14 H14B 109.9 . . ? C14 C14 H14B 109.9 5_565 . ? H14A C14 H14B 108.3 . . ? 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 O10 H10A O3 0.861(19) 2.35(5) 2.916(6) 124(5) 2_575 O9 H9C O5 0.91(2) 2.15(5) 2.795(5) 127(5) 4_566 N6 H6 O10 0.86 2.13 2.942(5) 157.3 8 N5 H5A O4 0.86 2.10 2.921(4) 158.8 7_575 C11 H11A O4 0.93 2.60 3.348(5) 138.4 7_575 O2 H2C O7 0.892(19) 2.00(2) 2.866(5) 164(5) 4_565 C5 H5 O8 0.93 2.56 3.477(5) 170.4 4_565 C8 H8A O7 0.93 2.59 3.502(5) 168.2 4_565 O2 H2B O4 0.888(19) 2.08(3) 2.866(5) 148(5) 4_566 C1 H1 O4 0.93 2.54 3.415(5) 157.2 4_566 O9 H9C O5 0.91(2) 2.15(5) 2.795(5) 127(5) 4_566 N2 H2A O6 0.86 2.01 2.853(4) 165.5 6_656 N3 H3 O9 0.86 2.09 2.864(6) 148.9 6_656 O1 H1B O6 0.853(19) 2.23(4) 2.966(6) 145(5) . O1 H1B O10 0.853(19) 2.59(5) 3.111(6) 120(4) . O10 H10B O9 0.855(19) 1.98(3) 2.793(7) 160(6) . C4 H4 O7 0.93 2.28 2.837(5) 118.2 . C9 H9A O8 0.93 2.28 2.832(5) 117.4 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.62 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.560 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.083 ###############END # Attachment '- bisurea complexes.cif' data_L _database_code_depnum_ccdc_archive 'CCDC 761486' #TrackingRef '- bisurea complexes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 N6 O6' _chemical_formula_weight 372.39 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' _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 7.2549(13) _cell_length_b 7.7629(15) _cell_length_c 9.1054(16) _cell_angle_alpha 98.095(3) _cell_angle_beta 99.515(3) _cell_angle_gamma 110.281(3) _cell_volume 463.39(15) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 198 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9691 _exptl_absorpt_correction_T_max 0.9772 _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 2373 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1620 _reflns_number_gt 1410 _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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1620 _refine_ls_number_parameters 130 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1654 _refine_ls_goodness_of_fit_ref 1.384 _refine_ls_restrained_S_all 1.386 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.26359(18) 0.7970(2) 0.67948(16) 0.0645(5) Uani 1 1 d . . . O2 O -0.0227(2) 0.9505(2) 0.63773(16) 0.0618(5) Uani 1 1 d D . . H2A H 0.062(3) 0.899(3) 0.658(3) 0.080 Uiso 1 1 d D . . H2B H -0.027(4) 0.973(4) 0.544(2) 0.080 Uiso 1 1 d D . . O3 O 0.0209(2) 0.1449(2) 0.92035(17) 0.0657(5) Uani 1 1 d D . . H3A H 0.105(3) 0.241(3) 0.974(3) 0.080 Uiso 1 1 d D . . H3B H 0.012(4) 0.064(3) 0.976(3) 0.080 Uiso 1 1 d D . . N1 N 0.2736(3) 0.4569(2) 0.1431(2) 0.0683(6) Uani 1 1 d . . . N2 N 0.5349(2) 0.8083(2) 0.57876(16) 0.0456(4) Uani 1 1 d . . . H2 H 0.6647 0.8544 0.5991 0.055 Uiso 1 1 calc R . . N3 N 0.5771(2) 0.9851(2) 0.81400(17) 0.0519(5) Uani 1 1 d . . . H3 H 0.7042 1.0220 0.8169 0.062 Uiso 1 1 calc R . . C1 C 0.1608(3) 0.5023(3) 0.2318(3) 0.0738(7) Uani 1 1 d . . . H1 H 0.0219 0.4530 0.1927 0.089 Uiso 1 1 calc R . . C2 C 0.2312(3) 0.6149(3) 0.3751(2) 0.0628(6) Uani 1 1 d . . . H2C H 0.1428 0.6404 0.4298 0.075 Uiso 1 1 calc R . . C3 C 0.4391(2) 0.6904(2) 0.43685(19) 0.0434(5) Uani 1 1 d . . . C4 C 0.5591(3) 0.6434(3) 0.3461(2) 0.0495(5) Uani 1 1 d . . . H4 H 0.6986 0.6902 0.3817 0.059 Uiso 1 1 calc R . . C5 C 0.4712(3) 0.5284(3) 0.2048(2) 0.0597(6) Uani 1 1 d . . . H5 H 0.5552 0.4981 0.1479 0.072 Uiso 1 1 calc R . . C6 C 0.4468(2) 0.8605(2) 0.6912(2) 0.0443(5) Uani 1 1 d . . . C7 C 0.5125(3) 1.0606(3) 0.9429(2) 0.0531(5) Uani 1 1 d . . . H7A H 0.3852 1.0727 0.9061 0.064 Uiso 1 1 calc R . . H7B H 0.6116 1.1851 0.9919 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0424(8) 0.0826(10) 0.0664(10) 0.0044(7) 0.0184(6) 0.0228(7) O2 0.0487(8) 0.0807(10) 0.0528(9) 0.0057(7) 0.0079(7) 0.0256(7) O3 0.0583(9) 0.0660(10) 0.0540(10) -0.0083(7) 0.0034(7) 0.0135(7) N1 0.0786(12) 0.0574(10) 0.0478(10) 0.0008(8) 0.0062(9) 0.0081(8) N2 0.0350(7) 0.0556(9) 0.0409(9) 0.0016(6) 0.0088(6) 0.0139(6) N3 0.0454(8) 0.0633(9) 0.0446(9) 0.0025(7) 0.0159(7) 0.0187(7) C1 0.0529(12) 0.0770(15) 0.0625(14) 0.0019(11) -0.0047(10) 0.0027(10) C2 0.0468(11) 0.0734(14) 0.0532(12) 0.0007(10) 0.0062(9) 0.0122(9) C3 0.0454(9) 0.0419(9) 0.0388(9) 0.0090(7) 0.0074(7) 0.0123(7) C4 0.0503(10) 0.0519(10) 0.0435(10) 0.0079(8) 0.0119(8) 0.0165(8) C5 0.0737(13) 0.0545(11) 0.0447(11) 0.0044(8) 0.0148(10) 0.0185(9) C6 0.0402(9) 0.0512(10) 0.0438(10) 0.0102(8) 0.0127(7) 0.0187(7) C7 0.0644(11) 0.0524(10) 0.0457(11) 0.0041(8) 0.0175(9) 0.0265(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.227(2) . ? N1 C5 1.331(3) . ? N1 C1 1.336(3) . ? N2 C6 1.379(2) . ? N2 C3 1.385(2) . ? N3 C6 1.339(2) . ? N3 C7 1.456(2) . ? C1 C2 1.370(3) . ? C2 C3 1.396(2) . ? C3 C4 1.395(2) . ? C4 C5 1.367(3) . ? C7 C7 1.490(4) 2_677 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 114.82(17) . . ? C6 N2 C3 127.68(14) . . ? C6 N3 C7 122.66(16) . . ? N1 C1 C2 125.92(19) . . ? C1 C2 C3 118.3(2) . . ? N2 C3 C2 125.64(16) . . ? N2 C3 C4 117.83(15) . . ? C2 C3 C4 116.53(17) . . ? C5 C4 C3 119.87(17) . . ? N1 C5 C4 124.5(2) . . ? O1 C6 N3 122.88(16) . . ? O1 C6 N2 122.52(16) . . ? N3 C6 N2 114.60(14) . . ? N3 C7 C7 112.31(19) . 2_677 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 1.0(4) . . . . ? N1 C1 C2 C3 -0.2(4) . . . . ? C6 N2 C3 C2 6.4(3) . . . . ? C6 N2 C3 C4 -174.28(15) . . . . ? C1 C2 C3 N2 179.14(18) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? N2 C3 C4 C5 -179.59(15) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C1 N1 C5 C4 -1.4(3) . . . . ? C3 C4 C5 N1 1.1(3) . . . . ? C7 N3 C6 O1 -1.9(3) . . . . ? C7 N3 C6 N2 178.39(15) . . . . ? C3 N2 C6 O1 3.8(3) . . . . ? C3 N2 C6 N3 -176.42(15) . . . . ? C6 N3 C7 C7 87.0(3) . . . 2_677 ? 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 C2 H2C O1 0.93 2.29 2.862(3) 119.3 . O2 H2A O1 0.852(16) 1.886(17) 2.732(2) 172(3) . N2 H2 O2 0.86 2.08 2.935(2) 176.2 1_655 N3 H3 O3 0.86 2.14 2.950(2) 156.4 1_665 O3 H3A N1 0.807(16) 1.975(17) 2.766(2) 166(3) 1_556 O2 H2B O2 0.891(16) 1.886(16) 2.762(3) 168(3) 2_576 O3 H3B O3 0.856(16) 1.950(16) 2.801(3) 173(3) 2_557 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.263 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.058 ##################### data_ZnAcL _database_code_depnum_ccdc_archive 'CCDC 777155' #TrackingRef '- bisurea complexes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 N6 O8 Zn' _chemical_formula_weight 533.84 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' Zn Zn 0.2839 1.4301 '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 10.447(2) _cell_length_b 10.755(3) _cell_length_c 12.474(3) _cell_angle_alpha 104.330(4) _cell_angle_beta 102.140(4) _cell_angle_gamma 110.924(3) _cell_volume 1197.3(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 block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7374 _exptl_absorpt_correction_T_max 0.7738 _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 6647 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.97 _reflns_number_total 4614 _reflns_number_gt 3353 _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^)+(0.0455P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4614 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.55567(4) -0.05026(4) 0.71618(3) 0.03606(14) Uani 1 1 d . . . O1 O 0.9697(3) 0.7018(2) 0.9579(2) 0.0507(6) Uani 1 1 d . . . O2 O -0.1938(2) -0.3815(3) 0.62042(19) 0.0541(7) Uani 1 1 d . . . O3 O 0.7517(3) -0.0534(3) 0.7141(3) 0.0709(8) Uani 1 1 d . . . O4 O 0.6199(3) -0.0818(3) 0.5458(3) 0.0721(9) Uani 1 1 d . . . O5 O 0.5735(2) -0.0534(2) 0.87954(19) 0.0428(6) Uani 1 1 d . . . O6 O 0.5300(3) -0.2773(2) 0.7972(2) 0.0523(7) Uani 1 1 d . . . O7 O 0.2434(4) 0.7753(4) 0.9354(3) 0.0650(9) Uani 1 1 d . . . O8 O 0.8007(4) 0.4904(3) 0.2159(2) 0.0850(10) Uani 1 1 d . . . H8A H 0.7791 0.4103 0.1713 0.127 Uiso 1 1 calc R . . N1 N 0.6106(3) 0.1626(3) 0.7557(2) 0.0354(6) Uani 1 1 d . . . N2 N 0.7313(3) 0.5980(2) 0.8396(2) 0.0363(6) Uani 1 1 d . . . H2A H 0.6605 0.6192 0.8181 0.044 Uiso 1 1 calc R . . N3 N 0.8773(3) 0.8302(3) 0.8769(2) 0.0461(8) Uani 1 1 d . . . H3 H 0.8058 0.8268 0.8254 0.055 Uiso 1 1 calc R . . N4 N 0.3397(3) -0.1596(3) 0.6290(2) 0.0326(6) Uani 1 1 d . . . N5 N -0.1088(3) -0.3966(3) 0.4648(2) 0.0361(7) Uani 1 1 d . . . H5A H -0.1360 -0.4309 0.3895 0.043 Uiso 1 1 calc R . . N6 N -0.3528(3) -0.5076(3) 0.4382(2) 0.0349(6) Uani 1 1 d . . . H6 H -0.3664 -0.5300 0.3643 0.042 Uiso 1 1 calc R . . C1 C 0.7497(4) 0.2573(3) 0.8095(3) 0.0413(8) Uani 1 1 d . . . H1 H 0.8183 0.2227 0.8268 0.050 Uiso 1 1 calc R . . C2 C 0.7978(3) 0.4016(3) 0.8407(3) 0.0396(8) Uani 1 1 d . . . H2 H 0.8959 0.4623 0.8780 0.047 Uiso 1 1 calc R . . C3 C 0.6970(3) 0.4556(3) 0.8154(3) 0.0333(7) Uani 1 1 d . . . C4 C 0.5526(3) 0.3581(3) 0.7605(3) 0.0385(8) Uani 1 1 d . . . H4 H 0.4814 0.3896 0.7429 0.046 Uiso 1 1 calc R . . C5 C 0.5149(3) 0.2154(3) 0.7323(3) 0.0390(8) Uani 1 1 d . . . H5 H 0.4175 0.1522 0.6949 0.047 Uiso 1 1 calc R . . C6 C 0.8686(4) 0.7109(3) 0.8953(3) 0.0370(8) Uani 1 1 d . . . C7 C 1.0037(4) 0.9657(3) 0.9409(3) 0.0470(9) Uani 1 1 d . . . H7A H 1.0081 1.0284 0.8962 0.056 Uiso 1 1 calc R . . H7B H 1.0911 0.9509 0.9512 0.056 Uiso 1 1 calc R . . C8 C 0.2779(3) -0.2193(3) 0.5119(3) 0.0372(8) Uani 1 1 d . . . H8 H 0.3374 -0.2072 0.4657 0.045 Uiso 1 1 calc R . . C9 C 0.1314(3) -0.2971(3) 0.4576(3) 0.0359(8) Uani 1 1 d . . . H9 H 0.0940 -0.3368 0.3762 0.043 Uiso 1 1 calc R . . C10 C 0.0378(3) -0.3176(3) 0.5226(3) 0.0318(7) Uani 1 1 d . . . C11 C 0.1017(3) -0.2550(3) 0.6446(3) 0.0419(9) Uani 1 1 d . . . H11 H 0.0448 -0.2643 0.6929 0.050 Uiso 1 1 calc R . . C12 C 0.2491(3) -0.1802(4) 0.6913(3) 0.0410(8) Uani 1 1 d . . . H12 H 0.2896 -0.1404 0.7726 0.049 Uiso 1 1 calc R . . C13 C -0.2186(3) -0.4271(3) 0.5156(3) 0.0350(8) Uani 1 1 d . . . C14 C -0.4753(3) -0.5571(3) 0.4794(3) 0.0359(8) Uani 1 1 d . . . H14A H -0.4482 -0.5885 0.5435 0.043 Uiso 1 1 calc R . . H14B H -0.5554 -0.6382 0.4165 0.043 Uiso 1 1 calc R . . C15 C 0.7362(4) -0.0656(4) 0.6092(4) 0.0464(9) Uani 1 1 d . . . C16 C 0.8567(5) -0.0614(5) 0.5624(5) 0.0842(15) Uani 1 1 d . . . H16A H 0.8179 -0.1303 0.4845 0.126 Uiso 1 1 calc R . . H16B H 0.9231 -0.0829 0.6119 0.126 Uiso 1 1 calc R . . H16C H 0.9069 0.0318 0.5606 0.126 Uiso 1 1 calc R . . C17 C 0.5608(3) -0.1729(4) 0.8851(3) 0.0389(8) Uani 1 1 d . . . C18 C 0.5844(4) -0.1869(4) 1.0042(3) 0.0538(10) Uani 1 1 d . . . H18A H 0.5072 -0.2721 0.9996 0.081 Uiso 1 1 calc R . . H18B H 0.5856 -0.1060 1.0592 0.081 Uiso 1 1 calc R . . H18C H 0.6755 -0.1914 1.0295 0.081 Uiso 1 1 calc R . . C19 C 0.7870(7) 0.5753(6) 0.1512(5) 0.1072(19) Uani 1 1 d . . . H19A H 0.8364 0.6734 0.2017 0.161 Uiso 1 1 calc R . . H19B H 0.6861 0.5509 0.1166 0.161 Uiso 1 1 calc R . . H19C H 0.8290 0.5605 0.0905 0.161 Uiso 1 1 calc R . . H7C H 0.298(6) 0.847(6) 0.984(5) 0.13(3) Uiso 1 1 d . . . H7D H 0.156(7) 0.739(6) 0.944(5) 0.13(2) 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 Zn 0.0315(2) 0.0276(2) 0.0414(2) 0.00757(16) 0.00990(16) 0.00862(16) O1 0.0403(14) 0.0360(14) 0.0605(16) 0.0142(11) 0.0028(12) 0.0096(11) O2 0.0349(13) 0.0713(17) 0.0307(13) 0.0020(12) 0.0111(10) 0.0062(12) O3 0.105(2) 0.085(2) 0.0667(19) 0.0424(16) 0.0447(17) 0.0693(19) O4 0.0574(19) 0.069(2) 0.072(2) 0.0072(15) 0.0158(15) 0.0232(15) O5 0.0463(14) 0.0330(13) 0.0441(14) 0.0104(10) 0.0113(11) 0.0160(11) O6 0.0531(15) 0.0428(14) 0.0453(14) 0.0013(12) 0.0006(12) 0.0223(12) O7 0.062(2) 0.066(2) 0.0518(18) 0.0084(16) 0.0194(16) 0.0189(17) O8 0.114(3) 0.073(2) 0.0400(16) 0.0083(15) 0.0142(17) 0.024(2) N1 0.0346(15) 0.0281(14) 0.0373(15) 0.0096(11) 0.0100(12) 0.0092(12) N2 0.0337(15) 0.0272(14) 0.0415(15) 0.0095(11) 0.0068(12) 0.0112(12) N3 0.0485(18) 0.0263(15) 0.0453(17) 0.0086(12) 0.0002(13) 0.0077(13) N4 0.0307(14) 0.0309(14) 0.0352(15) 0.0129(11) 0.0127(12) 0.0105(11) N5 0.0291(14) 0.0412(16) 0.0278(14) 0.0046(11) 0.0077(11) 0.0102(12) N6 0.0284(14) 0.0379(15) 0.0293(14) 0.0045(11) 0.0107(11) 0.0087(12) C1 0.041(2) 0.0342(19) 0.046(2) 0.0119(15) 0.0119(16) 0.0166(16) C2 0.0319(18) 0.0322(18) 0.0429(19) 0.0065(14) 0.0060(15) 0.0093(14) C3 0.0390(19) 0.0276(17) 0.0290(16) 0.0085(13) 0.0095(14) 0.0117(14) C4 0.0327(18) 0.0370(19) 0.0429(19) 0.0149(15) 0.0066(15) 0.0145(15) C5 0.0298(18) 0.0311(18) 0.045(2) 0.0127(15) 0.0052(15) 0.0059(14) C6 0.0363(19) 0.0298(18) 0.0359(18) 0.0063(14) 0.0104(15) 0.0089(15) C7 0.047(2) 0.0257(18) 0.054(2) 0.0091(15) 0.0120(18) 0.0065(16) C8 0.0329(18) 0.045(2) 0.0354(18) 0.0153(15) 0.0145(14) 0.0166(15) C9 0.0358(18) 0.0420(19) 0.0286(16) 0.0124(14) 0.0102(14) 0.0158(15) C10 0.0300(17) 0.0280(16) 0.0345(17) 0.0073(13) 0.0097(14) 0.0124(13) C11 0.0312(18) 0.051(2) 0.0326(18) 0.0077(15) 0.0129(15) 0.0092(16) C12 0.0364(19) 0.049(2) 0.0289(17) 0.0077(15) 0.0110(15) 0.0134(16) C13 0.0329(18) 0.0315(17) 0.0349(18) 0.0064(14) 0.0133(15) 0.0103(14) C14 0.0298(17) 0.0291(17) 0.0391(18) 0.0072(14) 0.0120(14) 0.0049(13) C15 0.058(3) 0.0325(19) 0.059(2) 0.0212(17) 0.030(2) 0.0215(18) C16 0.089(4) 0.091(4) 0.127(4) 0.061(3) 0.078(3) 0.058(3) C17 0.0300(18) 0.040(2) 0.041(2) 0.0124(16) 0.0074(15) 0.0137(15) C18 0.056(2) 0.057(2) 0.051(2) 0.0256(18) 0.0160(19) 0.025(2) C19 0.141(5) 0.106(5) 0.077(4) 0.037(3) 0.030(4) 0.056(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 Zn O5 2.016(2) . ? Zn N4 2.023(2) . ? Zn N1 2.049(3) . ? Zn O3 2.066(3) . ? Zn O4 2.342(3) . ? O1 O1 0.000(6) 1 ? O1 C6 1.226(4) . ? O2 O2 0.000(5) 1 ? O2 C13 1.211(3) . ? O3 C15 1.251(4) . ? O4 C15 1.229(5) . ? O5 C17 1.265(4) . ? O6 C17 1.246(4) . ? O7 H7C 0.77(6) . ? O7 H7D 0.90(6) . ? O8 C19 1.384(6) . ? O8 H8A 0.8200 . ? N1 C5 1.331(4) . ? N1 C1 1.339(4) . ? N2 C3 1.378(4) . ? N2 C6 1.390(4) . ? N2 H2A 0.8600 . ? N3 C6 1.333(4) . ? N3 C7 1.453(4) . ? N3 H3 0.8600 . ? N4 C12 1.340(4) . ? N4 C8 1.344(4) . ? N5 C10 1.375(4) . ? N5 C13 1.402(4) . ? N5 H5A 0.8600 . ? N6 C13 1.341(4) . ? N6 C14 1.453(4) . ? N6 H6 0.8600 . ? C1 C2 1.369(4) . ? C1 H1 0.9300 . ? C2 C3 1.390(4) . ? C2 H2 0.9300 . ? C3 C4 1.387(4) . ? C4 C5 1.370(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 O1 1.226(4) 1 ? C7 C7 1.509(6) 2_777 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.367(4) . ? C8 H8 0.9300 . ? C9 C10 1.390(4) . ? C9 H9 0.9300 . ? C10 C11 1.399(4) . ? C11 C12 1.365(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O2 1.211(3) 1 ? C14 C14 1.514(6) 2_446 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.486(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.507(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 O5 Zn N4 103.50(10) . . ? O5 Zn N1 97.32(10) . . ? N4 Zn N1 108.48(11) . . ? O5 Zn O3 96.94(11) . . ? N4 Zn O3 141.67(11) . . ? N1 Zn O3 100.52(11) . . ? O5 Zn O4 153.13(11) . . ? N4 Zn O4 94.36(10) . . ? N1 Zn O4 95.81(10) . . ? O3 Zn O4 57.54(11) . . ? O1 O1 C6 0(10) 1 . ? O2 O2 C13 0(10) 1 . ? C15 O3 Zn 97.9(3) . . ? C15 O4 Zn 85.4(2) . . ? C17 O5 Zn 111.8(2) . . ? H7C O7 H7D 114(5) . . ? C19 O8 H8A 109.5 . . ? C5 N1 C1 116.4(3) . . ? C5 N1 Zn 123.8(2) . . ? C1 N1 Zn 119.8(2) . . ? C3 N2 C6 126.8(3) . . ? C3 N2 H2A 116.6 . . ? C6 N2 H2A 116.6 . . ? C6 N3 C7 122.2(3) . . ? C6 N3 H3 118.9 . . ? C7 N3 H3 118.9 . . ? C12 N4 C8 116.1(3) . . ? C12 N4 Zn 118.5(2) . . ? C8 N4 Zn 125.4(2) . . ? C10 N5 C13 126.8(3) . . ? C10 N5 H5A 116.6 . . ? C13 N5 H5A 116.6 . . ? C13 N6 C14 119.9(3) . . ? C13 N6 H6 120.0 . . ? C14 N6 H6 120.0 . . ? N1 C1 C2 124.5(3) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 118.7(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? N2 C3 C4 118.4(3) . . ? N2 C3 C2 124.5(3) . . ? C4 C3 C2 117.1(3) . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 123.4(3) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? O1 C6 O1 0.0(3) 1 . ? O1 C6 N3 123.7(3) 1 . ? O1 C6 N3 123.7(3) . . ? O1 C6 N2 122.7(3) 1 . ? O1 C6 N2 122.7(3) . . ? N3 C6 N2 113.5(3) . . ? N3 C7 C7 110.5(3) . 2_777 ? N3 C7 H7A 109.5 . . ? C7 C7 H7A 109.5 2_777 . ? N3 C7 H7B 109.5 . . ? C7 C7 H7B 109.5 2_777 . ? H7A C7 H7B 108.1 . . ? N4 C8 C9 123.0(3) . . ? N4 C8 H8 118.5 . . ? C9 C8 H8 118.5 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? N5 C10 C9 119.0(3) . . ? N5 C10 C11 124.5(3) . . ? C9 C10 C11 116.4(3) . . ? C12 C11 C10 118.9(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N4 C12 C11 124.9(3) . . ? N4 C12 H12 117.5 . . ? C11 C12 H12 117.5 . . ? O2 C13 O2 0.0(2) 1 . ? O2 C13 N6 123.2(3) 1 . ? O2 C13 N6 123.2(3) . . ? O2 C13 N5 122.5(3) 1 . ? O2 C13 N5 122.5(3) . . ? N6 C13 N5 114.3(3) . . ? N6 C14 C14 112.5(3) . 2_446 ? N6 C14 H14A 109.1 . . ? C14 C14 H14A 109.1 2_446 . ? N6 C14 H14B 109.1 . . ? C14 C14 H14B 109.1 2_446 . ? H14A C14 H14B 107.8 . . ? O4 C15 O3 118.9(4) . . ? O4 C15 C16 120.8(4) . . ? O3 C15 C16 120.3(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 122.8(3) . . ? O6 C17 C18 119.6(3) . . ? O5 C17 C18 117.6(3) . . ? 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 H19A 109.5 . . ? O8 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O8 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O5 Zn O3 C15 173.9(2) . . . . ? N4 Zn O3 C15 51.6(3) . . . . ? N1 Zn O3 C15 -87.3(2) . . . . ? O4 Zn O3 C15 2.9(2) . . . . ? O5 Zn O4 C15 -23.1(3) . . . . ? N4 Zn O4 C15 -155.0(2) . . . . ? N1 Zn O4 C15 95.9(2) . . . . ? O3 Zn O4 C15 -2.9(2) . . . . ? N4 Zn O5 C17 76.4(2) . . . . ? N1 Zn O5 C17 -172.6(2) . . . . ? O3 Zn O5 C17 -71.0(2) . . . . ? O4 Zn O5 C17 -53.9(3) . . . . ? O5 Zn N1 C5 -103.3(3) . . . . ? N4 Zn N1 C5 3.6(3) . . . . ? O3 Zn N1 C5 158.2(3) . . . . ? O4 Zn N1 C5 100.2(3) . . . . ? O5 Zn N1 C1 75.9(2) . . . . ? N4 Zn N1 C1 -177.2(2) . . . . ? O3 Zn N1 C1 -22.6(3) . . . . ? O4 Zn N1 C1 -80.6(2) . . . . ? O5 Zn N4 C12 16.6(3) . . . . ? N1 Zn N4 C12 -86.0(3) . . . . ? O3 Zn N4 C12 136.9(2) . . . . ? O4 Zn N4 C12 176.4(2) . . . . ? O5 Zn N4 C8 -160.7(3) . . . . ? N1 Zn N4 C8 96.7(3) . . . . ? O3 Zn N4 C8 -40.5(3) . . . . ? O4 Zn N4 C8 -1.0(3) . . . . ? C5 N1 C1 C2 -0.2(5) . . . . ? Zn N1 C1 C2 -179.4(3) . . . . ? N1 C1 C2 C3 -0.1(5) . . . . ? C6 N2 C3 C4 179.0(3) . . . . ? C6 N2 C3 C2 -2.0(5) . . . . ? C1 C2 C3 N2 -178.5(3) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? N2 C3 C4 C5 178.3(3) . . . . ? C2 C3 C4 C5 -0.8(5) . . . . ? C1 N1 C5 C4 -0.1(5) . . . . ? Zn N1 C5 C4 179.1(2) . . . . ? C3 C4 C5 N1 0.6(5) . . . . ? O1 O1 C6 N3 0.0(9) 1 . . . ? O1 O1 C6 N2 0.0(8) 1 . . . ? C7 N3 C6 O1 -7.4(5) . . . 1 ? C7 N3 C6 O1 -7.4(5) . . . . ? C7 N3 C6 N2 170.4(3) . . . . ? C3 N2 C6 O1 -20.9(5) . . . 1 ? C3 N2 C6 O1 -20.9(5) . . . . ? C3 N2 C6 N3 161.3(3) . . . . ? C6 N3 C7 C7 -81.9(5) . . . 2_777 ? C12 N4 C8 C9 -0.1(5) . . . . ? Zn N4 C8 C9 177.3(2) . . . . ? N4 C8 C9 C10 0.4(5) . . . . ? C13 N5 C10 C9 -179.5(3) . . . . ? C13 N5 C10 C11 0.8(5) . . . . ? C8 C9 C10 N5 -179.9(3) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? N5 C10 C11 C12 179.3(3) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C8 N4 C12 C11 -0.5(5) . . . . ? Zn N4 C12 C11 -178.1(3) . . . . ? C10 C11 C12 N4 0.8(6) . . . . ? O2 O2 C13 N6 0.0(3) 1 . . . ? O2 O2 C13 N5 0.0(4) 1 . . . ? C14 N6 C13 O2 -6.8(5) . . . 1 ? C14 N6 C13 O2 -6.8(5) . . . . ? C14 N6 C13 N5 174.8(3) . . . . ? C10 N5 C13 O2 2.0(5) . . . 1 ? C10 N5 C13 O2 2.0(5) . . . . ? C10 N5 C13 N6 -179.7(3) . . . . ? C13 N6 C14 C14 78.8(5) . . . 2_446 ? Zn O4 C15 O3 4.7(3) . . . . ? Zn O4 C15 C16 -175.7(3) . . . . ? Zn O3 C15 O4 -5.3(4) . . . . ? Zn O3 C15 C16 175.0(3) . . . . ? Zn O5 C17 O6 -5.0(4) . . . . ? Zn O5 C17 C18 174.9(2) . . . . ? 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 C12 H12 O7 0.93 2.49 3.206(5) 134.2 1_545 C11 H11 O2 0.93 2.21 2.807(4) 121.6 1 C2 H2 O1 0.93 2.28 2.864(4) 120.1 1 O8 H8A O7 0.82 2.01 2.822(4) 171.8 2_666 O7 H7D O1 0.90(6) 1.89(6) 2.777(4) 167(6) 1_455 O7 H7C O5 0.77(6) 2.16(6) 2.927(4) 172(6) 2_667 N6 H6 O6 0.86 2.29 2.948(3) 133.8 2_546 N5 H5A O8 0.86 1.98 2.844(4) 179.8 1_445 N3 H3 O6 0.86 2.60 3.227(4) 130.8 1_565 N3 H3 O3 0.86 2.23 2.954(4) 141.4 1_565 N2 H2A O6 0.86 2.06 2.899(4) 164.8 1_565 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.364 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.064 ################### data_CdCl2L _database_code_depnum_ccdc_archive 'CCDC 777156' #TrackingRef '- bisurea complexes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H46 Cd Cl2 N14 O6' _chemical_formula_weight 930.15 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' Cd Cd -0.8075 1.2024 '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 31.510(7) _cell_length_b 8.534(2) _cell_length_c 18.891(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.100(2) _cell_angle_gamma 90.00 _cell_volume 4303.4(17) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1912 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7698 _exptl_absorpt_correction_T_max 0.8197 _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 17308 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.20 _reflns_number_total 5184 _reflns_number_gt 4634 _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^)+(0.0360P)^2^+3.5521P] 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 5184 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd Cd 0.2500 0.2500 0.5000 0.03008(6) Uani 1 2 d S . . Cl Cl 0.290529(17) 0.04022(6) 0.45159(3) 0.04187(11) Uani 1 1 d . . . O1 O 0.06507(5) 0.6213(2) 0.10623(9) 0.0586(4) Uani 1 1 d . . . O2 O 0.08515(5) 0.44819(16) -0.13394(10) 0.0485(3) Uani 1 1 d . . . O3 O 0.02864(7) -0.0412(3) 0.14494(18) 0.0976(8) Uani 1 1 d . . . N1 N 0.21700(5) 0.38258(19) 0.37146(9) 0.0377(3) Uani 1 1 d . . . N2 N 0.14114(5) 0.5553(2) 0.12626(9) 0.0439(4) Uani 1 1 d . . . H2 H 0.1584 0.5575 0.1032 0.053 Uiso 1 1 calc R . . N3 N 0.07575(5) 0.6306(2) -0.00202(9) 0.0433(4) Uani 1 1 d . . . H3 H 0.0963 0.6235 -0.0186 0.052 Uiso 1 1 calc R . . N4 N 0.01040(5) 0.43210(19) -0.14413(11) 0.0428(4) Uani 1 1 d . . . H4 H -0.0127 0.3719 -0.1481 0.051 Uiso 1 1 calc R . . N5 N 0.05395(6) 0.2078(2) -0.13013(13) 0.0497(4) Uani 1 1 d . . . H5 H 0.0266 0.1603 -0.1434 0.060 Uiso 1 1 calc R . . N6 N 0.17722(5) -0.08870(18) -0.05365(10) 0.0409(3) Uani 1 1 d . . . N7 N 0.10487(8) 0.0023(3) 0.16699(16) 0.0707(6) Uani 1 1 d . . . C1 C 0.23456(7) 0.3657(3) 0.32105(12) 0.0450(4) Uani 1 1 d . . . H1 H 0.2644 0.3113 0.3413 0.054 Uiso 1 1 calc R . . C2 C 0.21086(7) 0.4243(3) 0.24100(12) 0.0446(4) Uani 1 1 d . . . H2A H 0.2250 0.4112 0.2089 0.054 Uiso 1 1 calc R . . C3 C 0.16526(6) 0.5039(2) 0.20838(10) 0.0361(4) Uani 1 1 d . . . C4 C 0.14748(7) 0.5248(3) 0.26115(11) 0.0424(4) Uani 1 1 d . . . H4A H 0.1178 0.5790 0.2430 0.051 Uiso 1 1 calc R . . C5 C 0.17450(7) 0.4639(2) 0.34075(11) 0.0397(4) Uani 1 1 d . . . H5A H 0.1623 0.4804 0.3755 0.048 Uiso 1 1 calc R . . C6 C 0.09182(6) 0.6033(2) 0.07823(10) 0.0355(3) Uani 1 1 d . . . C7 C 0.02353(7) 0.6722(3) -0.06159(12) 0.0458(4) Uani 1 1 d . . . H7A H 0.0205 0.7853 -0.0669 0.055 Uiso 1 1 calc R . . H7B H 0.0030 0.6362 -0.0406 0.055 Uiso 1 1 calc R . . C8 C 0.00439(7) 0.6005(2) -0.14668(11) 0.0423(4) Uani 1 1 d . . . H8A H -0.0308 0.6257 -0.1832 0.051 Uiso 1 1 calc R . . H8B H 0.0222 0.6470 -0.1705 0.051 Uiso 1 1 calc R . . C9 C 0.05225(6) 0.3695(2) -0.13558(11) 0.0383(4) Uani 1 1 d . . . C10 C 0.09578(6) 0.1155(2) -0.10523(12) 0.0402(4) Uani 1 1 d . . . C11 C 0.08900(7) -0.0454(2) -0.11993(15) 0.0495(5) Uani 1 1 d . . . H11 H 0.0569 -0.0878 -0.1477 0.059 Uiso 1 1 calc R . . C12 C 0.12987(7) -0.1413(2) -0.09324(14) 0.0473(5) Uani 1 1 d . . . H12 H 0.1244 -0.2483 -0.1032 0.057 Uiso 1 1 calc R . . C13 C 0.18327(7) 0.0659(2) -0.04031(13) 0.0452(4) Uani 1 1 d . . . H13 H 0.2158 0.1051 -0.0132 0.054 Uiso 1 1 calc R . . C14 C 0.14495(7) 0.1715(2) -0.06367(13) 0.0445(4) Uani 1 1 d . . . H14 H 0.1517 0.2777 -0.0520 0.053 Uiso 1 1 calc R . . C15 C 0.07179(12) -0.0568(4) 0.1837(3) 0.0856(9) Uani 1 1 d . . . H15 H 0.0849 -0.1174 0.2318 0.103 Uiso 1 1 calc R . . C16 C 0.15791(13) -0.0251(6) 0.2289(3) 0.1375(18) Uani 1 1 d . . . H16A H 0.1610 -0.0956 0.2710 0.206 Uiso 1 1 calc R . . H16B H 0.1739 0.0726 0.2544 0.206 Uiso 1 1 calc R . . H16C H 0.1737 -0.0702 0.2020 0.206 Uiso 1 1 calc R . . C17 C 0.09038(18) 0.0828(6) 0.0927(3) 0.1403(18) Uani 1 1 d . . . H17A H 0.0551 0.0695 0.0539 0.210 Uiso 1 1 calc R . . H17B H 0.1084 0.0418 0.0687 0.210 Uiso 1 1 calc R . . H17C H 0.0978 0.1923 0.1045 0.210 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd 0.02565(9) 0.03996(10) 0.02808(9) 0.00418(6) 0.01660(7) 0.00129(6) Cl 0.0430(2) 0.0528(2) 0.0413(2) 0.00367(19) 0.03015(19) 0.00939(19) O1 0.0354(7) 0.1075(13) 0.0406(7) 0.0131(8) 0.0254(6) 0.0195(8) O2 0.0337(6) 0.0478(7) 0.0691(9) 0.0074(7) 0.0308(6) 0.0008(6) O3 0.0575(11) 0.0807(13) 0.174(2) 0.0136(14) 0.0743(14) 0.0014(10) N1 0.0324(7) 0.0521(9) 0.0329(7) 0.0090(6) 0.0203(6) 0.0058(6) N2 0.0318(7) 0.0760(11) 0.0321(7) 0.0149(7) 0.0225(6) 0.0134(7) N3 0.0355(7) 0.0656(10) 0.0328(7) 0.0108(7) 0.0209(6) 0.0129(7) N4 0.0319(7) 0.0463(8) 0.0561(9) 0.0040(7) 0.0273(7) 0.0039(6) N5 0.0300(7) 0.0428(8) 0.0798(13) 0.0029(8) 0.0315(8) 0.0000(6) N6 0.0318(7) 0.0420(8) 0.0505(9) -0.0001(7) 0.0229(7) 0.0017(6) N7 0.0492(11) 0.0742(13) 0.0989(17) -0.0124(12) 0.0462(11) -0.0119(10) C1 0.0328(8) 0.0676(12) 0.0406(9) 0.0163(9) 0.0235(8) 0.0146(8) C2 0.0363(9) 0.0689(13) 0.0395(9) 0.0148(9) 0.0275(8) 0.0128(9) C3 0.0297(8) 0.0506(10) 0.0307(8) 0.0072(7) 0.0178(7) 0.0045(7) C4 0.0349(8) 0.0630(12) 0.0349(8) 0.0092(8) 0.0222(7) 0.0138(8) C5 0.0376(9) 0.0556(11) 0.0338(8) 0.0052(8) 0.0243(7) 0.0064(8) C6 0.0312(8) 0.0457(9) 0.0325(8) 0.0052(7) 0.0189(7) 0.0047(7) C7 0.0410(9) 0.0545(11) 0.0390(9) 0.0091(8) 0.0193(8) 0.0190(9) C8 0.0355(8) 0.0500(10) 0.0363(9) 0.0099(8) 0.0157(7) 0.0127(8) C9 0.0296(8) 0.0442(9) 0.0431(9) 0.0030(8) 0.0207(7) 0.0026(7) C10 0.0314(8) 0.0419(9) 0.0525(10) 0.0023(8) 0.0258(8) 0.0010(7) C11 0.0295(8) 0.0445(10) 0.0719(13) -0.0022(10) 0.0252(9) -0.0053(7) C12 0.0375(9) 0.0391(9) 0.0664(13) -0.0018(9) 0.0283(9) -0.0018(8) C13 0.0290(8) 0.0452(10) 0.0577(11) -0.0032(9) 0.0206(8) -0.0017(7) C14 0.0320(8) 0.0387(10) 0.0586(12) -0.0044(8) 0.0212(8) -0.0026(7) C15 0.0790(19) 0.0761(18) 0.125(3) -0.0025(18) 0.070(2) 0.0022(15) C16 0.063(2) 0.158(4) 0.145(4) -0.026(3) 0.024(2) -0.018(2) C17 0.130(4) 0.152(4) 0.145(4) 0.042(3) 0.077(3) -0.016(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 Cd N1 2.3610(15) 7_556 ? Cd N1 2.3610(15) . ? Cd N6 2.3898(15) 6_556 ? Cd N6 2.3898(15) 4 ? Cd Cl 2.6294(6) 7_556 ? Cd Cl 2.6294(6) . ? O1 C6 1.220(2) . ? O2 C9 1.221(2) . ? O3 C15 1.160(4) . ? N1 C5 1.336(2) . ? N1 C1 1.339(2) . ? N2 C6 1.381(2) . ? N2 C3 1.387(2) . ? N3 C6 1.339(2) . ? N3 C7 1.460(2) . ? N4 C9 1.351(2) . ? N4 C8 1.447(2) . ? N5 C9 1.383(2) . ? N5 C10 1.386(2) . ? N6 C13 1.338(2) . ? N6 C12 1.342(2) . ? N6 Cd 2.3898(15) 4_545 ? N7 C15 1.338(4) . ? N7 C17 1.404(5) . ? N7 C16 1.462(4) . ? C1 C2 1.376(3) . ? C2 C3 1.402(2) . ? C3 C4 1.390(2) . ? C4 C5 1.377(2) . ? C7 C8 1.514(3) . ? C10 C11 1.394(3) . ? C10 C14 1.397(2) . ? C11 C12 1.376(3) . ? C13 C14 1.378(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd N1 180.00(5) 7_556 . ? N1 Cd N6 87.65(5) 7_556 6_556 ? N1 Cd N6 92.35(5) . 6_556 ? N1 Cd N6 92.35(5) 7_556 4 ? N1 Cd N6 87.65(5) . 4 ? N6 Cd N6 180.00(8) 6_556 4 ? N1 Cd Cl 89.91(4) 7_556 7_556 ? N1 Cd Cl 90.09(4) . 7_556 ? N6 Cd Cl 90.33(4) 6_556 7_556 ? N6 Cd Cl 89.67(4) 4 7_556 ? N1 Cd Cl 90.09(4) 7_556 . ? N1 Cd Cl 89.91(4) . . ? N6 Cd Cl 89.67(4) 6_556 . ? N6 Cd Cl 90.33(4) 4 . ? Cl Cd Cl 180.0 7_556 . ? C5 N1 C1 116.40(15) . . ? C5 N1 Cd 119.16(11) . . ? C1 N1 Cd 123.86(12) . . ? C6 N2 C3 125.82(14) . . ? C6 N3 C7 120.55(15) . . ? C9 N4 C8 119.92(16) . . ? C9 N5 C10 125.82(15) . . ? C13 N6 C12 116.08(16) . . ? C13 N6 Cd 118.67(12) . 4_545 ? C12 N6 Cd 125.16(13) . 4_545 ? C15 N7 C17 122.7(3) . . ? C15 N7 C16 117.0(3) . . ? C17 N7 C16 120.3(3) . . ? N1 C1 C2 123.66(16) . . ? C1 C2 C3 119.34(16) . . ? N2 C3 C4 124.84(16) . . ? N2 C3 C2 118.01(15) . . ? C4 C3 C2 117.15(16) . . ? C5 C4 C3 118.95(16) . . ? N1 C5 C4 124.43(16) . . ? O1 C6 N3 122.44(16) . . ? O1 C6 N2 123.23(16) . . ? N3 C6 N2 114.33(15) . . ? N3 C7 C8 111.72(15) . . ? N4 C8 C7 113.26(16) . . ? O2 C9 N4 123.19(18) . . ? O2 C9 N5 123.21(16) . . ? N4 C9 N5 113.59(16) . . ? N5 C10 C11 118.35(16) . . ? N5 C10 C14 124.52(18) . . ? C11 C10 C14 117.10(17) . . ? C12 C11 C10 119.87(17) . . ? N6 C12 C11 123.53(18) . . ? N6 C13 C14 124.87(17) . . ? C13 C14 C10 118.53(17) . . ? O3 C15 N7 127.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cd N1 C5 -161(100) 7_556 . . . ? N6 Cd N1 C5 61.26(15) 6_556 . . . ? N6 Cd N1 C5 -118.74(15) 4 . . . ? Cl Cd N1 C5 -29.07(14) 7_556 . . . ? Cl Cd N1 C5 150.93(14) . . . . ? N1 Cd N1 C1 28(100) 7_556 . . . ? N6 Cd N1 C1 -109.69(16) 6_556 . . . ? N6 Cd N1 C1 70.31(16) 4 . . . ? Cl Cd N1 C1 159.98(16) 7_556 . . . ? Cl Cd N1 C1 -20.02(16) . . . . ? C5 N1 C1 C2 -1.2(3) . . . . ? Cd N1 C1 C2 169.96(17) . . . . ? N1 C1 C2 C3 -1.3(3) . . . . ? C6 N2 C3 C4 -15.0(3) . . . . ? C6 N2 C3 C2 164.67(19) . . . . ? C1 C2 C3 N2 -177.1(2) . . . . ? C1 C2 C3 C4 2.6(3) . . . . ? N2 C3 C4 C5 178.18(19) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C1 N1 C5 C4 2.4(3) . . . . ? Cd N1 C5 C4 -169.19(16) . . . . ? C3 C4 C5 N1 -1.0(3) . . . . ? C7 N3 C6 O1 -4.7(3) . . . . ? C7 N3 C6 N2 176.00(18) . . . . ? C3 N2 C6 O1 8.0(3) . . . . ? C3 N2 C6 N3 -172.76(19) . . . . ? C6 N3 C7 C8 -143.31(19) . . . . ? C9 N4 C8 C7 -91.7(2) . . . . ? N3 C7 C8 N4 55.2(2) . . . . ? C8 N4 C9 O2 -3.8(3) . . . . ? C8 N4 C9 N5 177.09(17) . . . . ? C10 N5 C9 O2 14.2(3) . . . . ? C10 N5 C9 N4 -166.7(2) . . . . ? C9 N5 C10 C11 -166.5(2) . . . . ? C9 N5 C10 C14 15.6(3) . . . . ? N5 C10 C11 C12 -177.6(2) . . . . ? C14 C10 C11 C12 0.4(3) . . . . ? C13 N6 C12 C11 0.4(3) . . . . ? Cd N6 C12 C11 176.91(17) 4_545 . . . ? C10 C11 C12 N6 -0.8(4) . . . . ? C12 N6 C13 C14 0.4(3) . . . . ? Cd N6 C13 C14 -176.39(17) 4_545 . . . ? N6 C13 C14 C10 -0.7(3) . . . . ? N5 C10 C14 C13 178.1(2) . . . . ? C11 C10 C14 C13 0.3(3) . . . . ? C17 N7 C15 O3 -6.4(6) . . . . ? C16 N7 C15 O3 175.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 Cl 0.86 2.33 3.1908(16) 174.1 4 N4 H4 O1 0.86 2.18 2.861(2) 136.2 5_565 N5 H5 O3 0.86 2.00 2.846(2) 166.4 5 C5 H5A Cl 0.93 2.78 3.466(2) 131.0 7_556 C5 H5A O2 0.93 2.42 3.186(2) 139.5 6_566 N3 H3 O2 0.86 2.51 3.083(2) 125.0 . C4 H4A O1 0.93 2.24 2.813(2) 119.4 . C7 H7B O1 0.97 2.40 2.746(2) 100.3 . C8 H8B O2 0.97 2.42 2.752(2) 99.7 . C14 H14 O2 0.93 2.34 2.869(2) 116.1 . C17 H17A O3 0.96 2.46 2.815(5) 101.5 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.626 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.063 ################# data_CdSO4L _database_code_depnum_ccdc_archive 'CCDC 777157' #TrackingRef '- bisurea complexes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H28 Cd N6 O12 S' _chemical_formula_weight 616.88 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 30.671(12) _cell_length_b 7.551(3) _cell_length_c 24.101(10) _cell_angle_alpha 90.00 _cell_angle_beta 122.271(4) _cell_angle_gamma 90.00 _cell_volume 4720(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 1.085 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7732 _exptl_absorpt_correction_T_max 0.8123 _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 15660 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.55 _reflns_number_total 4383 _reflns_number_gt 3125 _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^)+(0.0386P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4383 _refine_ls_number_parameters 343 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.020 _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 Cd Cd 0.136918(11) 1.02310(4) 0.236436(14) 0.03739(12) Uani 1 1 d . . . S S 0.16308(4) 0.76228(18) 0.14314(5) 0.0441(3) Uani 1 1 d . . . O1 O -0.13418(10) 1.2677(5) 0.10282(14) 0.0552(9) Uani 1 1 d . . . O2 O 0.01281(11) 0.5804(4) 0.38629(14) 0.0463(8) Uani 1 1 d . . . O3 O 0.14743(13) 1.2815(5) 0.29480(16) 0.0563(10) Uani 1 1 d . . . O4 O 0.22480(11) 0.9841(5) 0.29398(15) 0.0471(8) Uani 1 1 d . . . O5 O 0.14728(18) 1.2070(5) 0.1669(2) 0.0741(13) Uani 1 1 d . . . O6 O 0.13421(10) 0.7854(4) 0.17599(14) 0.0501(8) Uani 1 1 d . . . O7 O 0.21842(10) 0.7792(5) 0.19280(14) 0.0547(9) Uani 1 1 d . . . O8 O 0.15209(12) 0.5892(5) 0.11298(16) 0.0696(11) Uani 1 1 d . . . O9 O 0.14792(14) 0.9037(5) 0.09486(15) 0.0756(11) Uani 1 1 d . . . O10 O 0.09031(14) 0.4865(5) 0.1880(2) 0.0832(13) Uani 1 1 d D . . O11 O 0.19308(18) 0.6902(8) 0.5730(2) 0.0918(17) Uani 1 1 d . . . O12 O 0.25659(18) 0.9835(9) 0.6366(3) 0.128(2) Uani 1 1 d D . . N1 N 0.04872(12) 1.0560(5) 0.16687(16) 0.0391(9) Uani 1 1 d . . . N2 N -0.10892(12) 1.1380(5) 0.03868(15) 0.0393(9) Uani 1 1 d . . . H2A H -0.1204 1.1023 -0.0007 0.047 Uiso 1 1 calc R . . N3 N -0.19190(13) 1.2278(6) -0.00517(17) 0.0617(13) Uani 1 1 d . . . H3 H -0.1972 1.1821 -0.0409 0.074 Uiso 1 1 calc R . . N4 N 0.12653(12) 0.8524(5) 0.30821(15) 0.0385(9) Uani 1 1 d . . . N5 N 0.09931(11) 0.6369(5) 0.44709(15) 0.0373(9) Uani 1 1 d . . . H5 H 0.1260 0.6361 0.4864 0.045 Uiso 1 1 calc R . . N6 N 0.05844(13) 0.5123(5) 0.49380(17) 0.0421(9) Uani 1 1 d . . . H6 H 0.0879 0.5196 0.5301 0.051 Uiso 1 1 calc R . . C1 C 0.02268(15) 0.9964(6) 0.1053(2) 0.0412(11) Uani 1 1 d . . . H1 H 0.0407 0.9343 0.0904 0.049 Uiso 1 1 calc R . . C2 C -0.02878(15) 1.0214(6) 0.06301(19) 0.0358(10) Uani 1 1 d . . . H2 H -0.0448 0.9779 0.0204 0.043 Uiso 1 1 calc R . . C3 C -0.05755(14) 1.1115(6) 0.08306(18) 0.0325(10) Uani 1 1 d . . . C4 C -0.03074(15) 1.1730(7) 0.14725(19) 0.0447(12) Uani 1 1 d . . . H4 H -0.0478 1.2340 0.1637 0.054 Uiso 1 1 calc R . . C5 C -0.14460(15) 1.2156(6) 0.0495(2) 0.0401(11) Uani 1 1 d . . . C6 C -0.23451(16) 1.3160(8) -0.0060(3) 0.0625(15) Uani 1 1 d . . . H6A H -0.2566 1.3729 -0.0481 0.075 Uiso 1 1 calc R . . H6B H -0.2211 1.4067 0.0277 0.075 Uiso 1 1 calc R . . C7 C 0.08090(15) 0.7784(7) 0.2899(2) 0.0485(13) Uani 1 1 d . . . H7 H 0.0554 0.7786 0.2455 0.058 Uiso 1 1 calc R . . C8 C 0.06940(15) 0.7031(6) 0.33208(19) 0.0449(12) Uani 1 1 d . . . H8 H 0.0370 0.6542 0.3163 0.054 Uiso 1 1 calc R . . C9 C 0.10642(14) 0.7001(6) 0.39860(19) 0.0345(10) Uani 1 1 d . . . C10 C 0.15474(14) 0.7701(6) 0.41803(19) 0.0400(11) Uani 1 1 d . . . H10 H 0.1813 0.7678 0.4620 0.048 Uiso 1 1 calc R . . C11 C 0.16270(15) 0.8426(6) 0.3716(2) 0.0427(11) Uani 1 1 d . . . H11 H 0.1953 0.8870 0.3855 0.051 Uiso 1 1 calc R . . C12 C 0.05346(15) 0.5745(6) 0.4389(2) 0.0351(10) Uani 1 1 d . . . C13 C 0.01526(16) 0.4322(6) 0.4939(2) 0.0423(11) Uani 1 1 d . . . H13A H 0.0282 0.3420 0.5277 0.051 Uiso 1 1 calc R . . H13B H -0.0074 0.3751 0.4520 0.051 Uiso 1 1 calc R . . C14 C 0.02109(16) 1.1427(7) 0.1859(2) 0.0482(13) Uani 1 1 d . . . H14 H 0.0383 1.1858 0.2286 0.058 Uiso 1 1 calc R . . H3A H 0.130(2) 1.347(8) 0.270(3) 0.080 Uiso 1 1 d . . . H4A H 0.237(2) 1.084(8) 0.292(2) 0.080 Uiso 1 1 d . . . H5A H 0.1521(19) 1.169(8) 0.137(2) 0.080 Uiso 1 1 d . . . H11A H 0.212(2) 0.760(8) 0.587(3) 0.080 Uiso 1 1 d . . . H12A H 0.2729(17) 0.945(8) 0.6811(14) 0.080 Uiso 1 1 d D . . H3B H 0.1418(18) 1.275(7) 0.329(2) 0.080 Uiso 1 1 d . . . H4B H 0.2275(19) 0.918(7) 0.265(3) 0.080 Uiso 1 1 d . . . H5B H 0.132(2) 1.289(8) 0.156(3) 0.080 Uiso 1 1 d . . . H10B H 0.0577(9) 0.507(7) 0.161(2) 0.080 Uiso 1 1 d D . . H11B H 0.201(2) 0.622(9) 0.597(3) 0.080 Uiso 1 1 d . . . H12B H 0.2848(13) 1.028(7) 0.642(2) 0.080 Uiso 1 1 d D . . H1OA H 0.1036(19) 0.598(7) 0.180(2) 0.080 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 Cd 0.03540(18) 0.0436(2) 0.03810(18) 0.00222(16) 0.02292(14) -0.00067(15) S 0.0377(6) 0.0534(9) 0.0363(6) -0.0075(6) 0.0165(5) 0.0071(5) O1 0.0484(19) 0.078(3) 0.0527(19) -0.0063(18) 0.0359(16) 0.0015(17) O2 0.0351(17) 0.059(2) 0.0472(18) 0.0050(16) 0.0234(15) -0.0050(15) O3 0.069(2) 0.059(3) 0.053(2) -0.0049(18) 0.040(2) 0.0003(18) O4 0.0396(17) 0.050(3) 0.0492(19) -0.0022(17) 0.0220(15) -0.0063(16) O5 0.126(4) 0.051(3) 0.089(3) 0.017(2) 0.087(3) 0.016(2) O6 0.0435(17) 0.051(2) 0.0629(19) -0.0147(17) 0.0330(16) -0.0049(15) O7 0.0325(16) 0.063(3) 0.0586(19) -0.0130(17) 0.0174(14) 0.0041(15) O8 0.053(2) 0.071(3) 0.074(2) -0.034(2) 0.0258(18) 0.0045(18) O9 0.102(3) 0.083(3) 0.0409(19) 0.0078(19) 0.038(2) 0.024(2) O10 0.049(2) 0.055(3) 0.112(3) 0.026(2) 0.021(2) 0.003(2) O11 0.079(3) 0.095(5) 0.061(3) 0.027(2) 0.011(2) -0.023(3) O12 0.082(3) 0.153(6) 0.165(5) -0.056(4) 0.076(4) -0.032(3) N1 0.0372(19) 0.042(3) 0.039(2) 0.0020(17) 0.0207(17) 0.0036(16) N2 0.0335(19) 0.057(3) 0.0308(18) 0.0001(17) 0.0195(16) 0.0033(17) N3 0.038(2) 0.103(4) 0.045(2) 0.007(2) 0.0229(19) 0.015(2) N4 0.037(2) 0.043(3) 0.040(2) 0.0052(18) 0.0234(17) -0.0029(17) N5 0.0301(18) 0.048(3) 0.0345(19) 0.0052(17) 0.0180(16) -0.0021(16) N6 0.039(2) 0.052(3) 0.046(2) 0.0066(18) 0.0303(17) -0.0017(17) C1 0.039(2) 0.045(3) 0.044(2) -0.002(2) 0.025(2) 0.003(2) C2 0.038(2) 0.042(3) 0.030(2) -0.004(2) 0.0203(19) 0.001(2) C3 0.034(2) 0.035(3) 0.032(2) 0.0057(19) 0.0194(19) -0.0038(19) C4 0.041(3) 0.060(4) 0.039(2) 0.002(2) 0.026(2) 0.002(2) C5 0.043(3) 0.042(3) 0.047(3) 0.007(2) 0.032(2) -0.002(2) C6 0.042(3) 0.079(5) 0.072(3) 0.017(3) 0.035(3) 0.018(3) C7 0.038(2) 0.068(4) 0.036(2) 0.007(2) 0.018(2) -0.010(2) C8 0.031(2) 0.059(4) 0.040(2) 0.007(2) 0.016(2) -0.010(2) C9 0.036(2) 0.034(3) 0.042(2) 0.004(2) 0.026(2) 0.0015(19) C10 0.034(2) 0.052(3) 0.035(2) 0.003(2) 0.0183(19) -0.004(2) C11 0.037(2) 0.049(3) 0.046(3) 0.001(2) 0.025(2) -0.007(2) C12 0.039(2) 0.028(3) 0.047(3) 0.002(2) 0.029(2) 0.0025(19) C13 0.052(3) 0.034(3) 0.057(3) 0.006(2) 0.040(2) 0.001(2) C14 0.047(3) 0.065(4) 0.032(2) -0.003(2) 0.020(2) 0.001(2) _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 Cd O6 2.285(3) . ? Cd N4 2.312(3) . ? Cd N1 2.313(3) . ? S O8 1.445(4) . ? S O9 1.461(4) . ? S O7 1.470(3) . ? S O6 1.480(3) . ? O1 C5 1.211(5) . ? O2 C12 1.216(5) . ? N1 C14 1.331(5) . ? N1 C1 1.333(5) . ? N2 C3 1.367(4) . ? N2 C5 1.384(5) . ? N3 C5 1.345(5) . ? N3 C6 1.457(5) . ? N4 C11 1.327(5) . ? N4 C7 1.344(5) . ? N5 C9 1.383(5) . ? N5 C12 1.394(5) . ? N6 C12 1.333(5) . ? N6 C13 1.457(5) . ? C1 C2 1.359(6) . ? C2 C3 1.389(5) . ? C3 C4 1.388(5) . ? C4 C14 1.366(5) . ? C6 C6 1.507(9) 7_475 ? C7 C8 1.365(5) . ? C8 C9 1.384(5) . ? C9 C10 1.398(5) . ? C10 C11 1.380(5) . ? C13 C13 1.518(8) 5_566 ? 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 O6 Cd N4 93.81(12) . . ? O6 Cd N1 89.54(11) . . ? N4 Cd N1 91.56(12) . . ? O8 S O9 111.8(2) . . ? O8 S O7 110.23(19) . . ? O9 S O7 108.9(2) . . ? O8 S O6 109.3(2) . . ? O9 S O6 108.2(2) . . ? O7 S O6 108.35(17) . . ? S O6 Cd 127.25(18) . . ? C14 N1 C1 115.9(4) . . ? C14 N1 Cd 121.1(3) . . ? C1 N1 Cd 123.0(3) . . ? C3 N2 C5 127.7(4) . . ? C5 N3 C6 122.3(4) . . ? C11 N4 C7 116.0(3) . . ? C11 N4 Cd 121.9(3) . . ? C7 N4 Cd 121.4(3) . . ? C9 N5 C12 126.9(3) . . ? C12 N6 C13 121.7(4) . . ? N1 C1 C2 123.6(4) . . ? C1 C2 C3 120.4(4) . . ? N2 C3 C2 118.7(4) . . ? N2 C3 C4 124.9(4) . . ? C2 C3 C4 116.3(4) . . ? C14 C4 C3 119.0(4) . . ? O1 C5 N3 123.6(4) . . ? O1 C5 N2 123.4(4) . . ? N3 C5 N2 113.0(4) . . ? N3 C6 C6 110.4(6) . 7_475 ? N4 C7 C8 124.5(4) . . ? C7 C8 C9 119.4(4) . . ? N5 C9 C8 125.6(4) . . ? N5 C9 C10 117.7(3) . . ? C8 C9 C10 116.7(4) . . ? C11 C10 C9 119.6(4) . . ? N4 C11 C10 123.7(4) . . ? O2 C12 N6 124.0(4) . . ? O2 C12 N5 122.0(4) . . ? N6 C12 N5 114.0(4) . . ? N6 C13 C13 112.1(5) . 5_566 ? N1 C14 C4 124.8(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H1OA O6 1.00(5) 1.73(5) 2.722(5) 172(5) . N2 H2A O9 0.86 1.95 2.789(5) 163.1 5_575 N3 H3 O9 0.86 2.55 3.255(5) 140.2 5_575 N5 H5 O11 0.86 2.04 2.885(5) 166.2 . N6 H6 O8 0.86 2.08 2.877(5) 153.0 6_566 O10 H10B O2 0.87(2) 1.91(2) 2.768(5) 170(5) 2 C4 H4 O1 0.93 2.25 2.845(5) 120.8 . C8 H8 O2 0.93 2.25 2.828(5) 120.0 . C10 H10 O11 0.93 2.57 3.318(6) 137.7 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.519 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.084