# 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 2019 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_red _database_code_depnum_ccdc_archive 'CCDC 1920748' loop_ _audit_author_name _audit_author_address 'KRISHNA MANNA' ;Indian Institute of Science India ; _audit_update_record ; 2019-06-04 deposited with the CCDC. 2019-07-29 downloaded from the CCDC. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Compound1 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Cd N2 O9 S' _chemical_formula_weight 520.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cd Cd -0.8075 1.2024 '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' O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.9378(3) _cell_length_b 10.8625(6) _cell_length_c 31.1686(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1671.79(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2930 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 25.00 _exptl_crystal_description Rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.492 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.764 _exptl_absorpt_correction_T_max 0.861 _exptl_absorpt_process_details SADBAS _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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36947 _diffrn_reflns_av_R_equivalents 0.0929 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2930 _reflns_number_gt 2525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex-II ccd' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al. 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0353P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_number_reflns 2930 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0598 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.26617(6) 0.25993(2) 0.259627(9) 0.02527(11) Uani 1 1 d . . . S1 S -0.1715(2) 0.52452(9) 0.51657(3) 0.0190(3) Uani 1 1 d . . . O1 O 0.7463(8) 0.5604(3) 0.34932(9) 0.0362(8) Uani 1 1 d . . . O2 O 0.6815(6) 0.2826(3) 0.29478(9) 0.0280(7) Uani 1 1 d . . . O3 O 1.0375(6) 0.4087(3) 0.29512(10) 0.0303(8) Uani 1 1 d . . . O4 O 0.6742(6) 0.3590(3) 0.68002(9) 0.0306(8) Uani 1 1 d . . . O5 O 1.0298(6) 0.6177(3) 0.71220(9) 0.0305(8) Uani 1 1 d . . . O6 O 0.9800(6) 0.4375(3) 0.74730(9) 0.0287(7) Uani 1 1 d . . . O7 O -0.2814(6) 0.6451(2) 0.50949(8) 0.0255(7) Uani 1 1 d . . . O8 O -0.3503(6) 0.4229(3) 0.52499(9) 0.0267(7) Uani 1 1 d . . . O9 O -0.0393(6) 0.1876(3) 0.21046(10) 0.0341(8) Uani 1 1 d . . . H9A H -0.1634 0.1387 0.2225 0.051 Uiso 1 1 d R . . H9B H 0.0429 0.1435 0.1901 0.051 Uiso 1 1 d R . . N1 N 0.4851(8) 0.3922(4) 0.36462(13) 0.0231(10) Uani 1 1 d . . . N2 N 0.6139(8) 0.5583(4) 0.66056(12) 0.0228(9) Uani 1 1 d . . . C1 C 0.3291(8) 0.4285(4) 0.40031(13) 0.0210(10) Uani 1 1 d . . . C2 C 0.1638(9) 0.3414(4) 0.41871(14) 0.0268(11) Uani 1 1 d . . . H2A H 0.1520 0.2634 0.4066 0.032 Uiso 1 1 calc R . . C3 C 0.0165(9) 0.3683(4) 0.45462(14) 0.0244(11) Uani 1 1 d . . . H3 H -0.0886 0.3081 0.4677 0.029 Uiso 1 1 calc R . . C4 C 0.0258(8) 0.4864(4) 0.47124(13) 0.0195(10) Uani 1 1 d . . . C5 C 0.1860(9) 0.5739(4) 0.45248(13) 0.0248(11) Uani 1 1 d . . . H5 H 0.1904 0.6530 0.4639 0.030 Uiso 1 1 calc R . . C6 C 0.3413(9) 0.5470(4) 0.41679(14) 0.0259(11) Uani 1 1 d . . . H6 H 0.4507 0.6065 0.4042 0.031 Uiso 1 1 calc R . . C7 C 0.0600(8) 0.5354(4) 0.56015(13) 0.0195(10) Uani 1 1 d . . . C8 C 0.1128(9) 0.4317(4) 0.58436(14) 0.0243(11) Uani 1 1 d . . . H8 H 0.0278 0.3577 0.5778 0.029 Uiso 1 1 calc R . . C9 C 0.2914(9) 0.4381(4) 0.61817(13) 0.0255(10) Uani 1 1 d . . . H9 H 0.3242 0.3687 0.6349 0.031 Uiso 1 1 calc R . . C10 C 0.4221(9) 0.5473(4) 0.62732(13) 0.0204(10) Uani 1 1 d . . . C11 C 0.3629(9) 0.6526(4) 0.60327(13) 0.0251(11) Uani 1 1 d . . . H11 H 0.4455 0.7271 0.6099 0.030 Uiso 1 1 calc R . . C12 C 0.1831(9) 0.6456(4) 0.57000(13) 0.0239(11) Uani 1 1 d . . . H12 H 0.1437 0.7155 0.5540 0.029 Uiso 1 1 calc R . . C13 C 0.6775(9) 0.4549(4) 0.34219(13) 0.0236(11) Uani 1 1 d . . . C14 C 0.8056(9) 0.3752(4) 0.30686(13) 0.0246(11) Uani 1 1 d . . . C15 C 0.7268(9) 0.4691(4) 0.68401(12) 0.0224(9) Uani 1 1 d . . . C16 C 0.9325(8) 0.5119(4) 0.71827(14) 0.0224(10) Uani 1 1 d . . . H1 H 0.467(8) 0.330(4) 0.3575(13) 0.007(12) Uiso 1 1 d . . . H2 H 0.658(7) 0.623(3) 0.6673(11) 0.000(11) 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 Cd1 0.02886(18) 0.02182(16) 0.02513(17) 0.00233(13) 0.00654(16) -0.00065(18) S1 0.0161(6) 0.0237(6) 0.0171(6) -0.0002(4) 0.0005(4) 0.0027(4) O1 0.045(2) 0.0260(16) 0.0375(19) -0.0074(13) 0.016(2) -0.010(2) O2 0.0258(17) 0.0257(16) 0.0324(18) -0.0071(13) -0.0005(13) -0.0013(14) O3 0.0222(18) 0.0294(18) 0.039(2) -0.0037(15) 0.0132(16) 0.0009(15) O4 0.036(2) 0.0201(16) 0.0352(19) 0.0046(13) -0.0219(16) -0.0032(15) O5 0.036(2) 0.0279(18) 0.0279(19) -0.0049(15) -0.0064(16) -0.0078(16) O6 0.0341(18) 0.0269(17) 0.0252(18) -0.0004(14) -0.0127(14) 0.0006(14) O7 0.0244(17) 0.0281(15) 0.0239(16) 0.0009(12) 0.0003(15) 0.0059(16) O8 0.0228(17) 0.0324(18) 0.0249(17) 0.0036(14) 0.0024(14) -0.0051(14) O9 0.031(2) 0.0305(17) 0.041(2) -0.0049(16) 0.0084(16) 0.0016(15) N1 0.027(2) 0.015(2) 0.027(2) -0.0060(19) 0.0084(19) -0.0053(19) N2 0.026(2) 0.015(2) 0.027(2) -0.0033(18) -0.0085(18) -0.0035(17) C1 0.024(3) 0.020(2) 0.019(2) -0.0017(18) 0.0029(19) 0.0010(19) C2 0.031(3) 0.020(2) 0.029(3) -0.010(2) 0.006(2) -0.002(2) C3 0.025(3) 0.017(2) 0.031(3) 0.003(2) 0.005(2) -0.003(2) C4 0.019(2) 0.027(3) 0.013(2) -0.0039(19) -0.0048(19) 0.002(2) C5 0.029(3) 0.018(2) 0.028(3) -0.0034(18) 0.001(2) 0.002(2) C6 0.029(3) 0.024(2) 0.024(3) 0.000(2) 0.007(2) -0.007(2) C7 0.013(2) 0.028(3) 0.018(2) -0.001(2) 0.0005(19) 0.001(2) C8 0.026(3) 0.021(2) 0.026(3) -0.001(2) -0.004(2) -0.003(2) C9 0.030(3) 0.019(2) 0.027(2) 0.0078(17) -0.008(2) 0.004(2) C10 0.022(2) 0.021(2) 0.018(2) -0.0034(19) 0.000(2) -0.001(2) C11 0.038(3) 0.014(2) 0.024(3) 0.0000(19) -0.007(2) 0.000(2) C12 0.030(3) 0.018(2) 0.024(3) 0.0072(18) 0.000(2) 0.004(2) C13 0.025(3) 0.031(3) 0.015(2) 0.0025(19) 0.0000(19) 0.004(2) C14 0.026(3) 0.028(2) 0.020(2) 0.0081(19) 0.002(2) 0.011(2) C15 0.024(2) 0.023(2) 0.021(2) -0.0013(17) 0.000(2) 0.003(2) C16 0.019(2) 0.026(3) 0.023(2) -0.009(2) 0.001(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 Cd1 O5 2.229(3) 2_664 ? Cd1 O3 2.261(3) 1_455 ? Cd1 O9 2.289(3) . ? Cd1 O4 2.327(3) 3_456 ? Cd1 O2 2.338(3) . ? Cd1 O6 2.400(3) 3_456 ? S1 O7 1.435(3) . ? S1 O8 1.438(3) . ? S1 C4 1.765(4) . ? S1 C7 1.779(4) . ? O1 C13 1.215(5) . ? O2 C14 1.236(5) . ? O3 C14 1.256(5) . ? O3 Cd1 2.261(3) 1_655 ? O4 C15 1.230(4) . ? O4 Cd1 2.327(3) 3_556 ? O5 C16 1.260(5) . ? O5 Cd1 2.229(3) 2_665 ? O6 C16 1.236(5) . ? O6 Cd1 2.400(3) 3_556 ? N1 C13 1.362(6) . ? N1 C1 1.409(5) . ? N2 C15 1.336(5) . ? N2 C10 1.409(5) . ? C1 C2 1.375(6) . ? C1 C6 1.387(6) . ? C2 C3 1.366(6) . ? C3 C4 1.383(6) . ? C4 C5 1.368(6) . ? C5 C6 1.382(6) . ? C7 C12 1.377(6) . ? C7 C8 1.381(6) . ? C8 C9 1.376(6) . ? C9 C10 1.380(6) . ? C10 C11 1.399(6) . ? C11 C12 1.367(6) . ? C13 C14 1.537(6) . ? C15 C16 1.545(6) . ? 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 Cd1 O3 97.12(12) 2_664 1_455 ? O5 Cd1 O9 93.35(12) 2_664 . ? O3 Cd1 O9 104.12(11) 1_455 . ? O5 Cd1 O4 162.87(11) 2_664 3_456 ? O3 Cd1 O4 84.49(10) 1_455 3_456 ? O9 Cd1 O4 102.83(11) . 3_456 ? O5 Cd1 O2 81.46(11) 2_664 . ? O3 Cd1 O2 97.66(11) 1_455 . ? O9 Cd1 O2 158.09(10) . . ? O4 Cd1 O2 81.42(11) 3_456 . ? O5 Cd1 O6 105.92(11) 2_664 3_456 ? O3 Cd1 O6 154.49(10) 1_455 3_456 ? O9 Cd1 O6 85.58(10) . 3_456 ? O4 Cd1 O6 70.27(10) 3_456 3_456 ? O2 Cd1 O6 75.55(10) . 3_456 ? O7 S1 O8 119.77(17) . . ? O7 S1 C4 107.46(18) . . ? O8 S1 C4 107.74(18) . . ? O7 S1 C7 107.44(18) . . ? O8 S1 C7 107.83(19) . . ? C4 S1 C7 105.80(19) . . ? C14 O2 Cd1 131.5(3) . . ? C14 O3 Cd1 113.0(3) . 1_655 ? C15 O4 Cd1 114.6(3) . 3_556 ? C16 O5 Cd1 128.1(3) . 2_665 ? C16 O6 Cd1 115.8(3) . 3_556 ? C13 N1 C1 130.3(4) . . ? C15 N2 C10 128.4(4) . . ? C2 C1 C6 120.6(4) . . ? C2 C1 N1 117.5(4) . . ? C6 C1 N1 121.9(4) . . ? C3 C2 C1 120.7(4) . . ? C2 C3 C4 119.2(4) . . ? C5 C4 C3 120.2(4) . . ? C5 C4 S1 119.8(3) . . ? C3 C4 S1 119.9(3) . . ? C4 C5 C6 121.1(4) . . ? C5 C6 C1 118.1(4) . . ? C12 C7 C8 120.3(4) . . ? C12 C7 S1 120.8(3) . . ? C8 C7 S1 119.0(3) . . ? C9 C8 C7 119.9(4) . . ? C8 C9 C10 120.1(4) . . ? C9 C10 C11 119.6(4) . . ? C9 C10 N2 122.6(4) . . ? C11 C10 N2 117.7(4) . . ? C12 C11 C10 119.8(4) . . ? C11 C12 C7 120.3(4) . . ? O1 C13 N1 124.9(4) . . ? O1 C13 C14 123.2(4) . . ? N1 C13 C14 111.9(4) . . ? O2 C14 O3 126.8(4) . . ? O2 C14 C13 118.2(4) . . ? O3 C14 C13 114.8(4) . . ? O4 C15 N2 124.2(4) . . ? O4 C15 C16 120.1(4) . . ? N2 C15 C16 115.7(3) . . ? O6 C16 O5 129.4(4) . . ? O6 C16 C15 115.7(3) . . ? O5 C16 C15 114.9(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.429 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.085