# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhan Shi' _publ_contact_author_email zshi@mail.jlu.edu.cn loop_ _publ_author_name 'Zhan Shi' 'Jing Li' # Attachment 'compound 1.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 871668' #TrackingRef 'compound 1.cif' # SQUEEZE RESULTS (APPEND TO CIF) 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 1 -0.017 0.000 0.000 524.1 169.4 2 0.035 0.500 0.500 524.1 169.2 _platon_squeeze_details ; The Platon SQUEEZE procedure was applied to recover 338 electrons per unit cell in one void (total volume 1048 ^A^3); there are 85 electrons per formula unit. Solvent water and DMF molecules (10 electrons/H2O, 40 electrons/DMF) were present, and the electrons recovered by SQUEEZE have been assigned as 4 water molecules and one DMF per formula unit. These four water and one DMF molecules have been included in the formula for the calculation of intensive properties. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C23 H29 Cd N5 O9 S2' _chemical_formula_sum 'C23 H29 Cd N5 O9 S2' _chemical_formula_weight 696.03 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 p2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2067(18) _cell_length_b 19.017(4) _cell_length_c 16.825(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.56(3) _cell_angle_gamma 90.00 _cell_volume 2895.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5090 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.955 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7957 _exptl_absorpt_correction_T_max 0.8418 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 16196 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5090 _reflns_number_gt 3507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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 SHELXP-97 _computing_publication_material SHELXTL _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. The Platon SQUEEZE procedure was applied to deal with the solvent molecules, the result showed that there were four water and one DMF molecules. ; _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^)+(0.0039P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5090 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 0.865 _refine_ls_restrained_S_all 0.865 _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 Cd1 Cd 0.18226(3) 0.440270(13) 0.017154(16) 0.02446(9) Uani 1 1 d . . . S1 S 0.03125(12) 0.66556(5) -0.18486(6) 0.0358(3) Uani 1 1 d . . . S2 S 0.42510(13) 0.23636(5) 0.20953(6) 0.0390(3) Uani 1 1 d . . . O1 O 0.0517(3) 0.55179(13) -0.06179(14) 0.0339(7) Uani 1 1 d . . . O2 O 0.2579(3) 0.50311(12) -0.08532(15) 0.0344(7) Uani 1 1 d . . . O3 O 0.2544(3) 0.35116(13) 0.11539(17) 0.0457(8) Uani 1 1 d . . . O4 O 0.3970(3) 0.36343(13) 0.02319(17) 0.0455(8) Uani 1 1 d . . . N1 N -0.0625(4) 0.86249(15) -0.42045(18) 0.0306(8) Uani 1 1 d . . . N2 N 0.2275(4) 0.65714(16) -0.27558(19) 0.0378(9) Uani 1 1 d . . . N3 N 0.7183(4) 0.02351(15) 0.38731(17) 0.0271(8) Uani 1 1 d . . . N4 N 0.6429(4) 0.18966(16) 0.14847(19) 0.0377(9) Uani 1 1 d . . . C1 C -0.1052(5) 0.8533(2) -0.3488(3) 0.0419(11) Uani 1 1 d . . . H1 H -0.1744 0.8841 -0.3344 0.080 Uiso 1 1 calc . . . C2 C -0.0507(5) 0.8001(2) -0.2958(2) 0.0432(12) Uani 1 1 d . . . H2 H -0.0830 0.7955 -0.2468 0.080 Uiso 1 1 calc . . . C3 C 0.0522(5) 0.75345(19) -0.3160(2) 0.0302(10) Uani 1 1 d . . . C4 C 0.1005(5) 0.7639(2) -0.3879(3) 0.0490(13) Uani 1 1 d . . . H4 H 0.1715 0.7345 -0.4031 0.080 Uiso 1 1 calc . . . C5 C 0.0414(6) 0.8190(2) -0.4370(3) 0.0521(14) Uani 1 1 d . . . H5 H 0.0765 0.8261 -0.4848 0.080 Uiso 1 1 calc . . . C6 C 0.1114(4) 0.69398(18) -0.2640(2) 0.0290(9) Uani 1 1 d . . . C7 C 0.1628(4) 0.59964(18) -0.1664(2) 0.0281(9) Uani 1 1 d . . . C8 C 0.2576(5) 0.60352(19) -0.2205(2) 0.0352(10) Uani 1 1 d . . . C9 C 0.1570(4) 0.54811(18) -0.0998(2) 0.0255(9) Uani 1 1 d . . . C10 C 0.3887(5) 0.5567(2) -0.2240(3) 0.0566(14) Uani 1 1 d . . . H10A H 0.3548 0.5106 -0.2415 0.080 Uiso 1 1 calc R . . H10B H 0.4495 0.5538 -0.1712 0.080 Uiso 1 1 calc R . . H10C H 0.4453 0.5760 -0.2614 0.080 Uiso 1 1 calc R . . C11 C 0.6135(5) 0.06949(19) 0.3985(2) 0.0309(10) Uani 1 1 d . . . H11 H 0.5744 0.0667 0.4456 0.080 Uiso 1 1 calc . . . C12 C 0.5614(5) 0.12101(19) 0.3423(2) 0.0342(10) Uani 1 1 d . . . H12 H 0.4891 0.1523 0.3520 0.080 Uiso 1 1 calc . . . C13 C 0.6180(5) 0.12576(18) 0.2711(2) 0.0311(10) Uani 1 1 d . . . C14 C 0.7239(5) 0.0760(2) 0.2590(2) 0.0405(11) Uani 1 1 d . . . H14 H 0.7615 0.0759 0.2113 0.080 Uiso 1 1 calc . . . C15 C 0.7721(5) 0.0269(2) 0.3185(2) 0.0371(11) Uani 1 1 d . . . H15 H 0.8446 -0.0051 0.3106 0.080 Uiso 1 1 calc . . . C16 C 0.5720(5) 0.18003(18) 0.2090(2) 0.0322(10) Uani 1 1 d . . . C17 C 0.4609(5) 0.27531(19) 0.1231(2) 0.0345(10) Uani 1 1 d . . . C18 C 0.5802(5) 0.2438(2) 0.0999(2) 0.0384(11) Uani 1 1 d . . . C19 C 0.3653(5) 0.3342(2) 0.0846(2) 0.0349(10) Uani 1 1 d . . . C20 C 0.6451(6) 0.2609(2) 0.0262(3) 0.0599(15) Uani 1 1 d . . . H20A H 0.5983 0.2326 -0.0184 0.080 Uiso 1 1 calc R . . H20B H 0.7492 0.2514 0.0372 0.080 Uiso 1 1 calc R . . H20C H 0.6291 0.3097 0.0130 0.080 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 Cd1 0.03211(17) 0.01777(14) 0.02202(15) -0.00004(13) 0.00105(11) 0.00031(14) S1 0.0425(7) 0.0329(6) 0.0352(6) 0.0149(5) 0.0157(5) 0.0094(5) S2 0.0429(8) 0.0358(6) 0.0418(6) 0.0153(5) 0.0167(6) 0.0142(5) O1 0.0403(18) 0.0357(16) 0.0287(15) 0.0074(13) 0.0144(13) 0.0018(14) O2 0.0374(19) 0.0301(14) 0.0361(16) 0.0117(12) 0.0081(14) 0.0067(14) O3 0.046(2) 0.0404(17) 0.0550(19) 0.0192(14) 0.0201(17) 0.0188(15) O4 0.049(2) 0.0406(17) 0.0489(18) 0.0236(14) 0.0142(16) 0.0152(15) N1 0.037(2) 0.0294(18) 0.0266(18) 0.0095(14) 0.0088(16) 0.0072(16) N2 0.040(2) 0.038(2) 0.040(2) 0.0184(16) 0.0186(18) 0.0113(18) N3 0.032(2) 0.0263(17) 0.0208(17) 0.0016(14) -0.0007(15) -0.0023(15) N4 0.043(2) 0.0363(19) 0.036(2) 0.0113(16) 0.0139(18) 0.0151(17) C1 0.049(3) 0.039(2) 0.041(3) 0.013(2) 0.016(2) 0.016(2) C2 0.055(3) 0.042(2) 0.038(2) 0.020(2) 0.025(2) 0.012(2) C3 0.033(3) 0.028(2) 0.030(2) 0.0105(18) 0.008(2) 0.0077(19) C4 0.057(3) 0.052(3) 0.046(3) 0.024(2) 0.030(3) 0.029(2) C5 0.070(4) 0.053(3) 0.041(3) 0.021(2) 0.031(3) 0.027(3) C6 0.027(3) 0.032(2) 0.028(2) 0.0134(17) 0.0034(19) 0.0081(19) C7 0.034(3) 0.019(2) 0.031(2) 0.0047(17) 0.005(2) 0.0014(18) C8 0.039(3) 0.033(2) 0.035(2) 0.0113(19) 0.011(2) 0.005(2) C9 0.029(2) 0.023(2) 0.022(2) -0.0019(17) -0.0010(18) -0.0007(19) C10 0.063(4) 0.057(3) 0.055(3) 0.028(3) 0.023(3) 0.031(3) C11 0.035(3) 0.028(2) 0.030(2) 0.0019(18) 0.0066(19) 0.0043(19) C12 0.035(3) 0.029(2) 0.038(2) 0.0049(19) 0.005(2) 0.0068(19) C13 0.035(3) 0.027(2) 0.031(2) 0.0066(18) 0.005(2) 0.0077(19) C14 0.050(3) 0.037(2) 0.036(2) 0.0094(19) 0.012(2) 0.019(2) C15 0.042(3) 0.035(2) 0.034(2) 0.0065(19) 0.005(2) 0.017(2) C16 0.037(3) 0.028(2) 0.032(2) 0.0059(18) 0.007(2) 0.0081(19) C17 0.036(3) 0.031(2) 0.036(2) 0.0121(18) 0.006(2) 0.001(2) C18 0.042(3) 0.037(2) 0.038(3) 0.015(2) 0.013(2) 0.006(2) C19 0.038(3) 0.029(2) 0.035(2) 0.0047(19) -0.001(2) 0.003(2) C20 0.065(4) 0.067(3) 0.057(3) 0.025(3) 0.036(3) 0.021(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 Cd1 O2 2.308(2) . ? Cd1 N3 2.321(3) 2_655 ? Cd1 N1 2.322(3) 2_544 ? Cd1 O3 2.375(3) . ? Cd1 O1 2.412(3) 3_565 ? Cd1 O4 2.446(3) . ? Cd1 C19 2.738(4) . ? S1 C6 1.724(4) . ? S1 C7 1.731(4) . ? S2 C17 1.717(4) . ? S2 C16 1.727(4) . ? O1 C9 1.257(4) . ? O1 Cd1 2.412(3) 3_565 ? O2 C9 1.254(4) . ? O3 C19 1.268(5) . ? O4 C19 1.254(4) . ? N1 C5 1.332(5) . ? N1 C1 1.346(5) . ? N1 Cd1 2.322(3) 2_554 ? N2 C6 1.322(5) . ? N2 C8 1.371(4) . ? N3 C15 1.341(5) . ? N3 C11 1.341(5) . ? N3 Cd1 2.321(3) 2_645 ? N4 C16 1.319(5) . ? N4 C18 1.374(5) . ? C1 C2 1.382(5) . ? C1 H1 0.9300 . ? C2 C3 1.384(5) . ? C2 H2 0.9300 . ? C3 C4 1.378(5) . ? C3 C6 1.472(5) . ? C4 C5 1.382(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.374(5) . ? C7 C9 1.498(5) . ? C8 C10 1.509(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.385(5) . ? C11 H11 0.9300 . ? C12 C13 1.394(5) . ? C12 H12 0.9300 . ? C13 C14 1.401(5) . ? C13 C16 1.475(5) . ? C14 C15 1.382(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.369(5) . ? C17 C19 1.496(5) . ? C18 C20 1.507(5) . ? 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 O2 Cd1 N3 91.70(10) . 2_655 ? O2 Cd1 N1 88.62(10) . 2_544 ? N3 Cd1 N1 174.76(11) 2_655 2_544 ? O2 Cd1 O3 143.61(10) . . ? N3 Cd1 O3 88.86(10) 2_655 . ? N1 Cd1 O3 93.98(10) 2_544 . ? O2 Cd1 O1 127.53(9) . 3_565 ? N3 Cd1 O1 90.16(10) 2_655 3_565 ? N1 Cd1 O1 85.51(10) 2_544 3_565 ? O3 Cd1 O1 88.85(9) . 3_565 ? O2 Cd1 O4 89.31(9) . . ? N3 Cd1 O4 99.53(11) 2_655 . ? N1 Cd1 O4 85.70(11) 2_544 . ? O3 Cd1 O4 54.83(9) . . ? O1 Cd1 O4 141.78(8) 3_565 . ? O2 Cd1 C19 116.37(12) . . ? N3 Cd1 C19 94.64(11) 2_655 . ? N1 Cd1 C19 89.90(12) 2_544 . ? O3 Cd1 C19 27.56(10) . . ? O1 Cd1 C19 115.71(11) 3_565 . ? O4 Cd1 C19 27.26(10) . . ? C6 S1 C7 88.90(18) . . ? C17 S2 C16 89.47(19) . . ? C9 O1 Cd1 167.9(2) . 3_565 ? C9 O2 Cd1 100.6(2) . . ? C19 O3 Cd1 92.4(2) . . ? C19 O4 Cd1 89.5(2) . . ? C5 N1 C1 116.4(3) . . ? C5 N1 Cd1 121.1(2) . 2_554 ? C1 N1 Cd1 122.1(3) . 2_554 ? C6 N2 C8 111.3(3) . . ? C15 N3 C11 118.6(3) . . ? C15 N3 Cd1 118.0(2) . 2_645 ? C11 N3 Cd1 123.3(2) . 2_645 ? C16 N4 C18 110.5(3) . . ? N1 C1 C2 122.8(4) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 119.6(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 118.0(3) . . ? C4 C3 C6 119.2(4) . . ? C2 C3 C6 122.8(3) . . ? C3 C4 C5 118.6(4) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 124.4(4) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? N2 C6 C3 122.8(3) . . ? N2 C6 S1 114.8(3) . . ? C3 C6 S1 122.4(3) . . ? C8 C7 C9 130.2(3) . . ? C8 C7 S1 110.5(3) . . ? C9 C7 S1 119.2(3) . . ? N2 C8 C7 114.4(4) . . ? N2 C8 C10 118.5(3) . . ? C7 C8 C10 127.1(3) . . ? O2 C9 O1 123.6(3) . . ? O2 C9 C7 117.7(3) . . ? O1 C9 C7 118.8(3) . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 122.2(3) . . ? N3 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C11 C12 C13 119.7(4) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 117.5(3) . . ? C12 C13 C16 123.4(4) . . ? C14 C13 C16 119.1(3) . . ? C15 C14 C13 119.4(4) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N3 C15 C14 122.5(4) . . ? N3 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? N4 C16 C13 121.7(4) . . ? N4 C16 S2 114.6(3) . . ? C13 C16 S2 123.6(3) . . ? C18 C17 C19 130.0(4) . . ? C18 C17 S2 109.9(3) . . ? C19 C17 S2 120.0(3) . . ? C17 C18 N4 115.5(3) . . ? C17 C18 C20 126.8(4) . . ? N4 C18 C20 117.7(4) . . ? O4 C19 O3 123.3(4) . . ? O4 C19 C17 118.8(4) . . ? O3 C19 C17 117.9(4) . . ? O4 C19 Cd1 63.3(2) . . ? O3 C19 Cd1 60.1(2) . . ? C17 C19 Cd1 177.9(3) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.450 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.083 # Attachment 'compound 2.cif' data_compound-2 _database_code_depnum_ccdc_archive 'CCDC 871669' #TrackingRef 'compound 2.cif' # SQUEEZE RESULTS (APPEND TO CIF) 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 1 -0.018 0.000 0.000 510.8 151.8 2 0.051 0.500 0.500 510.8 152.0 _platon_squeeze_details ; The Platon SQUEEZE procedure was applied to recover 303 electrons per unit cell in one void (total volume 1021 ^A^3); that is 80 electrons per formula unit. Solvent water and DMF molecules (10 electrons/H2O, 40 electrons/DMF) were present, and the electrons recovered by SQUEEZE have been assigned as 3 water and one DMF molecules per formula unit. These three water and DMF molecules have been included in the formula for the calculation of intensive properties. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C23 H27 Mn N5 O8 S2' _chemical_formula_sum 'C23 H27 Mn N5 O8 S2' _chemical_formula_weight 620.56 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1726(18) _cell_length_b 18.956(4) _cell_length_c 16.748(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.13(3) _cell_angle_gamma 90.00 _cell_volume 2847.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5013 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8437 _exptl_absorpt_correction_T_max 0.8748 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 16019 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5013 _reflns_number_gt 3338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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 SHELXP-97 _computing_publication_material SHELXTL _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. The Platon SQUEEZE procedure was applied to deal with the solvent molecules, and the diffraction points of 2 Theta > 50\~awere deleted. ; _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^)+(0.0288P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5013 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_restrained_S_all 0.855 _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 Mn1 Mn 0.18163(4) 0.437875(18) 0.02118(2) 0.02693(11) Uani 1 1 d . . . S1 S 0.02007(7) 0.66637(3) -0.18452(4) 0.03775(18) Uani 1 1 d . . . S2 S 0.43300(7) 0.24042(4) 0.21005(4) 0.04264(19) Uani 1 1 d . . . O1 O 0.02932(18) 0.55778(9) -0.05911(10) 0.0378(4) Uani 1 1 d . . . O2 O 0.23198(17) 0.50175(8) -0.07639(10) 0.0355(4) Uani 1 1 d . . . O3 O 0.26070(19) 0.35509(9) 0.11585(12) 0.0484(5) Uani 1 1 d . . . O4 O 0.39831(19) 0.37043(9) 0.02431(11) 0.0487(5) Uani 1 1 d . . . N1 N -0.0698(2) 0.85970(10) -0.42478(12) 0.0355(5) Uani 1 1 d . . . N2 N 0.2146(2) 0.65203(11) -0.27320(13) 0.0399(6) Uani 1 1 d . . . N3 N 0.7207(2) 0.02151(10) 0.38687(12) 0.0305(5) Uani 1 1 d . . . N4 N 0.6444(2) 0.19204(11) 0.14771(13) 0.0408(6) Uani 1 1 d . . . C1 C -0.1091(3) 0.85192(14) -0.35371(18) 0.0468(7) Uani 1 1 d . . . H1 H -0.1769 0.8839 -0.3403 0.080 Uiso 1 1 calc . . . C2 C -0.0559(3) 0.79923(15) -0.29806(17) 0.0492(8) Uani 1 1 d . . . H2 H -0.0869 0.7964 -0.2488 0.080 Uiso 1 1 calc . . . C3 C 0.0449(3) 0.75048(13) -0.31710(15) 0.0350(6) Uani 1 1 d . . . C4 C 0.0889(3) 0.76016(15) -0.38948(18) 0.0569(9) Uani 1 1 d . . . H4 H 0.1593 0.7301 -0.4040 0.080 Uiso 1 1 calc . . . C5 C 0.0295(3) 0.81404(16) -0.44071(18) 0.0589(9) Uani 1 1 d . . . H5 H 0.0610 0.8188 -0.4897 0.080 Uiso 1 1 calc . . . C6 C 0.1023(3) 0.69122(13) -0.26308(15) 0.0347(6) Uani 1 1 d . . . C7 C 0.1462(2) 0.59806(12) -0.16261(14) 0.0296(6) Uani 1 1 d . . . C8 C 0.2416(3) 0.59916(13) -0.21508(15) 0.0364(6) Uani 1 1 d . . . C9 C 0.1360(3) 0.54947(12) -0.09512(14) 0.0272(6) Uani 1 1 d . . . C10 C 0.3685(3) 0.54979(15) -0.21564(18) 0.0573(9) Uani 1 1 d . . . H10A H 0.4109 0.5353 -0.1608 0.080 Uiso 1 1 calc R . . H10B H 0.4431 0.5733 -0.2384 0.080 Uiso 1 1 calc R . . H10C H 0.3328 0.5091 -0.2481 0.080 Uiso 1 1 calc R . . C11 C 0.6185(3) 0.06918(13) 0.39743(14) 0.0333(6) Uani 1 1 d . . . H11 H 0.5805 0.0668 0.4447 0.080 Uiso 1 1 calc . . . C12 C 0.5672(3) 0.12161(13) 0.34139(15) 0.0343(6) Uani 1 1 d . . . H12 H 0.4959 0.1535 0.3512 0.080 Uiso 1 1 calc . . . C13 C 0.6218(3) 0.12680(12) 0.27039(15) 0.0330(6) Uani 1 1 d . . . C14 C 0.7248(3) 0.07591(14) 0.25854(16) 0.0447(7) Uani 1 1 d . . . H14 H 0.7626 0.0762 0.2112 0.080 Uiso 1 1 calc . . . C15 C 0.7699(3) 0.02543(13) 0.31712(16) 0.0411(7) Uani 1 1 d . . . H15 H 0.8386 -0.0080 0.3079 0.080 Uiso 1 1 calc . . . C16 C 0.5763(3) 0.18246(12) 0.20853(16) 0.0350(6) Uani 1 1 d . . . C17 C 0.4657(3) 0.27954(13) 0.12304(15) 0.0360(6) Uani 1 1 d . . . C18 C 0.5822(3) 0.24680(13) 0.09885(16) 0.0390(7) Uani 1 1 d . . . C19 C 0.3701(3) 0.33940(13) 0.08519(16) 0.0362(6) Uani 1 1 d . . . C20 C 0.6435(3) 0.26393(16) 0.02534(17) 0.0592(9) Uani 1 1 d . . . H20A H 0.5776 0.2460 -0.0226 0.080 Uiso 1 1 calc R . . H20B H 0.7400 0.2426 0.0306 0.080 Uiso 1 1 calc R . . H20C H 0.6523 0.3142 0.0208 0.080 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 Mn1 0.0347(2) 0.0216(2) 0.0225(2) -0.00043(17) 0.00144(16) -0.00005(16) S1 0.0447(4) 0.0353(4) 0.0366(4) 0.0138(3) 0.0163(3) 0.0105(3) S2 0.0481(4) 0.0400(4) 0.0436(4) 0.0163(3) 0.0182(4) 0.0162(3) O1 0.0428(10) 0.0423(11) 0.0302(10) 0.0064(9) 0.0122(9) -0.0030(8) O2 0.0485(10) 0.0271(10) 0.0301(10) 0.0082(8) 0.0061(8) 0.0070(8) O3 0.0496(11) 0.0418(12) 0.0569(13) 0.0214(10) 0.0181(11) 0.0181(9) O4 0.0515(11) 0.0461(12) 0.0490(12) 0.0241(10) 0.0115(10) 0.0117(9) N1 0.0419(12) 0.0362(13) 0.0301(12) 0.0089(10) 0.0116(11) 0.0095(10) N2 0.0401(13) 0.0419(14) 0.0404(14) 0.0166(11) 0.0144(11) 0.0102(10) N3 0.0366(12) 0.0271(12) 0.0252(12) -0.0005(9) 0.0003(10) 0.0034(9) N4 0.0439(13) 0.0417(14) 0.0374(13) 0.0127(11) 0.0097(12) 0.0121(10) C1 0.0564(18) 0.0420(17) 0.0469(18) 0.0151(15) 0.0223(16) 0.0193(13) C2 0.0640(19) 0.0503(18) 0.0397(17) 0.0193(15) 0.0257(15) 0.0193(15) C3 0.0345(14) 0.0363(16) 0.0348(15) 0.0150(13) 0.0090(13) 0.0036(11) C4 0.073(2) 0.060(2) 0.0496(19) 0.0292(17) 0.0397(17) 0.0340(16) C5 0.081(2) 0.060(2) 0.0468(19) 0.0302(16) 0.0386(18) 0.0346(17) C6 0.0354(14) 0.0376(16) 0.0323(15) 0.0129(12) 0.0096(13) 0.0039(12) C7 0.0345(14) 0.0281(14) 0.0252(14) 0.0074(11) 0.0041(12) 0.0032(11) C8 0.0377(15) 0.0369(16) 0.0350(15) 0.0108(13) 0.0083(13) 0.0065(12) C9 0.0360(14) 0.0225(14) 0.0203(13) -0.0011(11) -0.0004(12) -0.0082(11) C10 0.0538(18) 0.062(2) 0.063(2) 0.0240(17) 0.0266(16) 0.0291(15) C11 0.0396(15) 0.0307(14) 0.0276(14) 0.0002(12) 0.0021(12) -0.0013(12) C12 0.0381(14) 0.0295(15) 0.0344(15) -0.0005(13) 0.0058(13) 0.0046(11) C13 0.0391(14) 0.0286(14) 0.0299(14) 0.0031(12) 0.0045(12) 0.0028(11) C14 0.0540(17) 0.0486(18) 0.0358(16) 0.0116(14) 0.0195(14) 0.0203(14) C15 0.0501(16) 0.0387(17) 0.0344(16) 0.0088(13) 0.0085(14) 0.0188(13) C16 0.0412(15) 0.0294(15) 0.0343(15) 0.0073(12) 0.0072(13) 0.0060(11) C17 0.0374(14) 0.0349(15) 0.0350(15) 0.0078(13) 0.0064(13) 0.0060(12) C18 0.0420(15) 0.0397(16) 0.0355(16) 0.0117(13) 0.0089(13) 0.0046(13) C19 0.0385(15) 0.0275(14) 0.0390(17) 0.0053(13) 0.0002(14) -0.0016(12) C20 0.065(2) 0.068(2) 0.0521(19) 0.0271(17) 0.0278(17) 0.0197(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 2.1603(16) . ? Mn1 O1 2.1613(17) 3_565 ? Mn1 O3 2.2404(17) . ? Mn1 N3 2.2601(19) 2_655 ? Mn1 N1 2.271(2) 2_544 ? Mn1 O4 2.3546(17) . ? Mn1 C19 2.616(3) . ? S1 C6 1.714(2) . ? S1 C7 1.724(2) . ? S2 C17 1.717(3) . ? S2 C16 1.718(2) . ? O1 C9 1.263(3) . ? O1 Mn1 2.1613(17) 3_565 ? O2 C9 1.255(3) . ? O3 C19 1.255(3) . ? O4 C19 1.251(3) . ? N1 C1 1.322(3) . ? N1 C5 1.324(3) . ? N1 Mn1 2.271(2) 2_554 ? N2 C6 1.309(3) . ? N2 C8 1.383(3) . ? N3 C11 1.340(3) . ? N3 C15 1.340(3) . ? N3 Mn1 2.2601(19) 2_645 ? N4 C16 1.314(3) . ? N4 C18 1.370(3) . ? C1 C2 1.383(3) . ? C1 H1 0.9300 . ? C2 C3 1.391(3) . ? C2 H2 0.9300 . ? C3 C4 1.368(3) . ? C3 C6 1.469(3) . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.365(3) . ? C7 C9 1.476(3) . ? C8 C10 1.495(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 C13 1.387(3) . ? C12 H12 0.9300 . ? C13 C14 1.393(3) . ? C13 C16 1.476(3) . ? C14 C15 1.371(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.368(3) . ? C17 C19 1.492(3) . ? C18 C20 1.493(3) . ? 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 O2 Mn1 O1 123.22(6) . 3_565 ? O2 Mn1 O3 147.04(7) . . ? O1 Mn1 O3 89.73(7) 3_565 . ? O2 Mn1 N3 90.29(7) . 2_655 ? O1 Mn1 N3 91.40(7) 3_565 2_655 ? O3 Mn1 N3 89.20(7) . 2_655 ? O2 Mn1 N1 87.96(7) . 2_544 ? O1 Mn1 N1 86.29(7) 3_565 2_544 ? O3 Mn1 N1 94.40(7) . 2_544 ? N3 Mn1 N1 175.71(7) 2_655 2_544 ? O2 Mn1 O4 90.43(7) . . ? O1 Mn1 O4 144.87(6) 3_565 . ? O3 Mn1 O4 57.16(6) . . ? N3 Mn1 O4 98.84(7) 2_655 . ? N1 Mn1 O4 85.10(7) 2_544 . ? O2 Mn1 C19 118.82(8) . . ? O1 Mn1 C19 117.52(8) 3_565 . ? O3 Mn1 C19 28.64(7) . . ? N3 Mn1 C19 95.05(7) 2_655 . ? N1 Mn1 C19 89.23(8) 2_544 . ? O4 Mn1 C19 28.53(7) . . ? C6 S1 C7 89.20(11) . . ? C17 S2 C16 89.59(12) . . ? C9 O1 Mn1 167.63(15) . 3_565 ? C9 O2 Mn1 110.04(15) . . ? C19 O3 Mn1 92.53(15) . . ? C19 O4 Mn1 87.42(15) . . ? C1 N1 C5 116.0(2) . . ? C1 N1 Mn1 123.01(16) . 2_554 ? C5 N1 Mn1 120.69(17) . 2_554 ? C6 N2 C8 110.5(2) . . ? C11 N3 C15 116.8(2) . . ? C11 N3 Mn1 124.85(16) . 2_645 ? C15 N3 Mn1 118.36(15) . 2_645 ? C16 N4 C18 111.2(2) . . ? N1 C1 C2 124.2(2) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 118.9(2) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 116.6(2) . . ? C4 C3 C6 120.9(2) . . ? C2 C3 C6 122.4(2) . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 124.1(2) . . ? N1 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? N2 C6 C3 122.9(2) . . ? N2 C6 S1 115.36(18) . . ? C3 C6 S1 121.63(18) . . ? C8 C7 C9 130.9(2) . . ? C8 C7 S1 110.12(17) . . ? C9 C7 S1 118.97(18) . . ? C7 C8 N2 114.8(2) . . ? C7 C8 C10 126.9(2) . . ? N2 C8 C10 118.3(2) . . ? O2 C9 O1 123.0(2) . . ? O2 C9 C7 119.2(2) . . ? O1 C9 C7 117.9(2) . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 123.0(2) . . ? N3 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C11 C12 C13 120.1(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 116.8(2) . . ? C12 C13 C16 123.5(2) . . ? C14 C13 C16 119.7(2) . . ? C15 C14 C13 119.5(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? N3 C15 C14 123.8(2) . . ? N3 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? N4 C16 C13 122.2(2) . . ? N4 C16 S2 114.37(18) . . ? C13 C16 S2 123.4(2) . . ? C18 C17 C19 130.2(2) . . ? C18 C17 S2 110.00(18) . . ? C19 C17 S2 119.81(19) . . ? C17 C18 N4 114.8(2) . . ? C17 C18 C20 126.8(2) . . ? N4 C18 C20 118.4(2) . . ? O4 C19 O3 122.9(2) . . ? O4 C19 C17 120.0(2) . . ? O3 C19 C17 117.1(2) . . ? O4 C19 Mn1 64.05(13) . . ? O3 C19 Mn1 58.83(13) . . ? C17 C19 Mn1 174.82(18) . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.280 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.050