Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Vimal K. Jain' _publ_contact_author_address ; Chemistry Division Bhabha Atomic Research Centre Mumbai 400 085 INDIA ; _publ_contact_author_email JAINVK@APSARA.BARC.ERNET.IN _publ_section_title ; Group 12 metal monoselenocarboxylates: Synthesis, characterization, structure and their transformation to metal selenide (MSe; M = Zn, Cd, Hg) nanoparticles ; loop_ _publ_author_name 'Vimal K. Jain' 'G. Kedarnath' 'Liladhar B. Kumbhare' 'Munirathinam Nethaji' 'Prasad P. Phadnis' # Attachment 'ppcdorm_.cif' data_ppcdorm_ _database_code_depnum_ccdc_archive 'CCDC 290980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H13 CD0.5 N O SE' _chemical_formula_sum 'C10 H13 Cd0.50 N O Se' _chemical_formula_weight 298.37 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' Se Se -0.0929 2.2259 '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 ORTHORHOMBIC _symmetry_space_group_name_H-M PBCN loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 20.997(4) _cell_length_b 8.2420(16) _cell_length_c 13.556(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2346.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 27.42 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour 'LIGHT ORANGE' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 4.050 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.3282 _exptl_absorpt_correction_T_max 0.4681 _exptl_absorpt_process_details 'SADABS, SHELXL-97' _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 SMART APEX CCD' _diffrn_measurement_method OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11952 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2575 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX CCD' _computing_cell_refinement 'BRUKER SMART APEX CCD' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'WINGX V1.64.05' _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^)+(0.0466P)^2^+0.1605P] 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 2575 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.0000 0.09840(5) 0.2500 0.04674(15) Uani 1 2 d S . . Se1 Se 0.01856(2) 0.25847(7) 0.08848(4) 0.06697(19) Uani 1 1 d . . . O1 O 0.11921(15) 0.2521(4) 0.2156(2) 0.0648(8) Uani 1 1 d . . . N1 N -0.06983(18) -0.1243(4) 0.2407(3) 0.0571(10) Uani 1 1 d . . . C1 C 0.14113(18) 0.4278(5) 0.0830(3) 0.0438(10) Uani 1 1 d . . . C2 C 0.2001(2) 0.4696(6) 0.1216(5) 0.0659(14) Uani 1 1 d . . . C3 C 0.2387(3) 0.5773(7) 0.0723(6) 0.084(2) Uani 1 1 d . . . C4 C 0.2200(3) 0.6436(7) -0.0143(5) 0.0814(18) Uani 1 1 d . . . C5 C 0.1624(3) 0.6030(6) -0.0548(4) 0.0733(15) Uani 1 1 d . . . C6 C 0.1232(3) 0.4951(6) -0.0054(4) 0.0575(12) Uani 1 1 d . . . C7 C 0.10030(19) 0.3117(5) 0.1388(3) 0.0459(10) Uani 1 1 d . . . C8 C -0.0301(3) -0.2670(7) 0.2203(5) 0.0639(13) Uani 1 1 d . . . C9 C -0.1020(4) -0.1441(9) 0.3386(6) 0.0828(19) Uani 1 1 d . . . C10 C -0.1174(4) -0.1044(11) 0.1620(7) 0.092(2) Uani 1 1 d . . . H2 H 0.209(2) 0.423(5) 0.175(3) 0.054(14) Uiso 1 1 d . . . H3 H 0.273(3) 0.600(7) 0.092(4) 0.10(2) Uiso 1 1 d . . . H4 H 0.245(3) 0.714(6) -0.047(4) 0.089(17) Uiso 1 1 d . . . H5 H 0.151(2) 0.654(7) -0.116(4) 0.092(18) Uiso 1 1 d . . . H6 H 0.090(2) 0.476(6) -0.025(3) 0.062(17) Uiso 1 1 d . . . H81 H -0.0194(18) -0.259(4) 0.155(3) 0.043(11) Uiso 1 1 d . . . H82 H -0.053(2) -0.363(6) 0.237(3) 0.072(16) Uiso 1 1 d . . . H91 H -0.131(2) -0.059(6) 0.338(4) 0.078(18) Uiso 1 1 d . . . H92 H -0.135(3) -0.226(7) 0.325(4) 0.090(18) Uiso 1 1 d . . . H93 H -0.070(4) -0.162(10) 0.395(5) 0.16(3) Uiso 1 1 d . . . H101 H -0.144(3) -0.190(8) 0.167(4) 0.11(2) Uiso 1 1 d . . . H102 H -0.098(3) -0.082(6) 0.105(3) 0.07(2) Uiso 1 1 d . . . H103 H -0.143(3) -0.009(7) 0.179(4) 0.10(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 Cd1 0.0472(2) 0.0429(3) 0.0501(3) 0.000 0.00980(19) 0.000 Se1 0.0518(3) 0.0879(4) 0.0613(3) 0.0235(3) -0.0063(2) -0.0165(2) O1 0.068(2) 0.072(2) 0.0551(18) 0.0157(17) -0.0092(15) -0.0055(18) N1 0.055(2) 0.050(2) 0.066(3) -0.0048(19) 0.0058(19) -0.0059(17) C1 0.042(2) 0.035(2) 0.054(3) -0.0021(19) 0.0009(18) 0.0041(17) C2 0.050(3) 0.051(3) 0.097(4) 0.014(3) -0.012(3) 0.004(2) C3 0.047(3) 0.058(4) 0.148(6) 0.011(4) -0.002(3) -0.005(3) C4 0.062(4) 0.062(4) 0.120(5) 0.016(4) 0.025(4) -0.012(3) C5 0.089(4) 0.066(4) 0.065(4) 0.015(3) 0.011(3) -0.009(3) C6 0.058(3) 0.058(3) 0.057(3) 0.003(2) 0.002(3) -0.009(3) C7 0.051(2) 0.042(3) 0.045(2) -0.0032(19) -0.0009(19) 0.0029(19) C8 0.069(3) 0.051(3) 0.071(4) -0.001(3) 0.009(3) 0.001(3) C9 0.078(4) 0.065(4) 0.106(5) 0.001(4) 0.044(4) -0.010(4) C10 0.072(4) 0.080(5) 0.124(7) -0.013(5) -0.027(4) -0.004(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 Cd1 N1 2.353(4) . ? Cd1 N1 2.353(4) 3 ? Cd1 Se1 2.5859(6) 3 ? Cd1 Se1 2.5859(6) . ? Se1 C7 1.898(4) . ? O1 C7 1.217(5) . ? N1 C8 1.468(6) . ? N1 C10 1.471(8) . ? N1 C9 1.499(6) . ? C1 C6 1.374(6) . ? C1 C2 1.387(6) . ? C1 C7 1.491(5) . ? C2 C3 1.377(7) . ? C2 H2 0.83(4) . ? C3 C4 1.353(8) . ? C3 H3 0.79(6) . ? C4 C5 1.370(8) . ? C4 H4 0.90(5) . ? C5 C6 1.384(7) . ? C5 H5 0.96(5) . ? C6 H6 0.76(4) . ? C8 C8 1.498(11) 3 ? C8 H81 0.92(4) . ? C8 H82 0.96(5) . ? C9 H91 0.93(5) . ? C9 H92 0.99(6) . ? C9 H93 1.04(8) . ? C10 H101 0.91(6) . ? C10 H102 0.89(5) . ? C10 H103 0.97(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 N1 Cd1 N1 77.44(18) . 3 ? N1 Cd1 Se1 110.46(9) . 3 ? N1 Cd1 Se1 116.52(9) 3 3 ? N1 Cd1 Se1 116.52(9) . . ? N1 Cd1 Se1 110.46(9) 3 . ? Se1 Cd1 Se1 118.64(3) 3 . ? C7 Se1 Cd1 87.12(13) . . ? C8 N1 C10 109.8(5) . . ? C8 N1 C9 109.6(5) . . ? C10 N1 C9 110.4(6) . . ? C8 N1 Cd1 106.3(3) . . ? C10 N1 Cd1 112.0(4) . . ? C9 N1 Cd1 108.6(4) . . ? C6 C1 C2 118.3(4) . . ? C6 C1 C7 123.0(4) . . ? C2 C1 C7 118.7(4) . . ? C3 C2 C1 120.2(6) . . ? C3 C2 H2 125(3) . . ? C1 C2 H2 115(3) . . ? C4 C3 C2 120.7(6) . . ? C4 C3 H3 118(4) . . ? C2 C3 H3 122(4) . . ? C3 C4 C5 120.4(6) . . ? C3 C4 H4 121(4) . . ? C5 C4 H4 119(4) . . ? C4 C5 C6 119.2(6) . . ? C4 C5 H5 117(3) . . ? C6 C5 H5 124(3) . . ? C1 C6 C5 121.3(5) . . ? C1 C6 H6 118(4) . . ? C5 C6 H6 120(4) . . ? O1 C7 C1 120.3(4) . . ? O1 C7 Se1 120.6(3) . . ? C1 C7 Se1 119.1(3) . . ? N1 C8 C8 112.2(4) . 3 ? N1 C8 H81 105(2) . . ? C8 C8 H81 108(2) 3 . ? N1 C8 H82 109(3) . . ? C8 C8 H82 107(3) 3 . ? H81 C8 H82 114(4) . . ? N1 C9 H91 101(3) . . ? N1 C9 H92 103(3) . . ? H91 C9 H92 94(4) . . ? N1 C9 H93 112(4) . . ? H91 C9 H93 123(6) . . ? H92 C9 H93 120(5) . . ? N1 C10 H101 107(4) . . ? N1 C10 H102 110(3) . . ? H101 C10 H102 120(5) . . ? N1 C10 H103 107(3) . . ? H101 C10 H103 106(5) . . ? H102 C10 H103 106(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 N1 Cd1 Se1 C7 -151.51(15) . . . . ? N1 Cd1 Se1 C7 -65.70(16) 3 . . . ? Se1 Cd1 Se1 C7 72.62(12) 3 . . . ? N1 Cd1 N1 C8 -14.2(3) 3 . . . ? Se1 Cd1 N1 C8 -128.1(3) 3 . . . ? Se1 Cd1 N1 C8 92.6(3) . . . . ? N1 Cd1 N1 C10 -134.2(5) 3 . . . ? Se1 Cd1 N1 C10 111.9(4) 3 . . . ? Se1 Cd1 N1 C10 -27.4(4) . . . . ? N1 Cd1 N1 C9 103.6(4) 3 . . . ? Se1 Cd1 N1 C9 -10.3(4) 3 . . . ? Se1 Cd1 N1 C9 -149.6(4) . . . . ? C6 C1 C2 C3 0.7(8) . . . . ? C7 C1 C2 C3 -179.6(5) . . . . ? C1 C2 C3 C4 -0.1(9) . . . . ? C2 C3 C4 C5 -0.7(10) . . . . ? C3 C4 C5 C6 0.9(9) . . . . ? C2 C1 C6 C5 -0.5(7) . . . . ? C7 C1 C6 C5 179.8(4) . . . . ? C4 C5 C6 C1 -0.3(8) . . . . ? C6 C1 C7 O1 178.0(4) . . . . ? C2 C1 C7 O1 -1.7(6) . . . . ? C6 C1 C7 Se1 -2.0(5) . . . . ? C2 C1 C7 Se1 178.2(3) . . . . ? Cd1 Se1 C7 O1 6.0(3) . . . . ? Cd1 Se1 C7 C1 -174.0(3) . . . . ? C10 N1 C8 C8 163.3(7) . . . 3 ? C9 N1 C8 C8 -75.3(7) . . . 3 ? Cd1 N1 C8 C8 41.9(6) . . . 3 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.888 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.089