# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _publ_contact_author_name 'Chong-Hyeak Kim' _publ_contact_author_email chkim@krict.re.kr loop_ _publ_author_name 'Nilkamal Maiti' 'Sang Hyuk Im' 'Yong Hui Lee' 'Chong-Hyeak Kim' 'Sang Il Seok' # Attachment '20100415.cif' data_20100415 _database_code_depnum_ccdc_archive 'CCDC 806675' #TrackingRef '20100415.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(N,N-dimethylselenourea)trichloro antimony hemiacetone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H38 Cl6 N8 O Sb2 Se4' _chemical_formula_weight 1118.57 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 28.4879(5) _cell_length_b 32.7675(6) _cell_length_c 7.9990(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7466.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9911 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.91 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.990 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4256 _exptl_absorpt_coefficient_mu 5.800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2935 _exptl_absorpt_correction_T_max 0.7223 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 32438 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4238 _reflns_number_gt 3869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. ; _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^)+(0.0199P)^2^+2.5699P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000072(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.014(6) _refine_ls_number_reflns 4238 _refine_ls_number_parameters 170 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0202 _refine_ls_wR_factor_ref 0.0441 _refine_ls_wR_factor_gt 0.0433 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb Sb 0.447728(7) 0.294978(5) 0.62487(2) 0.03924(6) Uani 1 1 d . . . Se1 Se 0.368941(12) 0.245796(12) 0.51865(5) 0.05867(10) Uani 1 1 d . . . N1 N 0.36212(11) 0.19740(9) 0.2316(4) 0.0583(7) Uani 1 1 d . . . N2 N 0.40725(11) 0.25364(9) 0.2024(4) 0.0680(9) Uani 1 1 d . . . H2A H 0.4121 0.2475 0.0994 0.082 Uiso 1 1 calc R . . H2B H 0.4197 0.2753 0.2442 0.082 Uiso 1 1 calc R . . C1 C 0.38071(10) 0.22995(9) 0.2965(4) 0.0439(7) Uani 1 1 d . . . C2 C 0.36672(16) 0.18787(14) 0.0540(6) 0.0823(13) Uani 1 1 d . . . H2C H 0.3647 0.2126 -0.0100 0.123 Uiso 1 1 calc R . . H2D H 0.3420 0.1697 0.0211 0.123 Uiso 1 1 calc R . . H2E H 0.3965 0.1751 0.0342 0.123 Uiso 1 1 calc R . . C3 C 0.3354(2) 0.16836(15) 0.3299(7) 0.118(2) Uani 1 1 d . . . H3A H 0.3453 0.1697 0.4445 0.177 Uiso 1 1 calc R . . H3B H 0.3405 0.1413 0.2875 0.177 Uiso 1 1 calc R . . H3C H 0.3026 0.1749 0.3228 0.177 Uiso 1 1 calc R . . Se11 Se 0.509080(15) 0.358843(11) 0.72918(4) 0.06597(12) Uani 1 1 d . . . N11 N 0.54401(9) 0.38205(9) 1.0406(4) 0.0536(7) Uani 1 1 d . . . N12 N 0.51058(11) 0.31917(8) 1.0343(4) 0.0667(8) Uani 1 1 d . . . H12A H 0.5163 0.3163 1.1392 0.080 Uiso 1 1 calc R . . H12B H 0.4968 0.2999 0.9802 0.080 Uiso 1 1 calc R . . C11 C 0.52284(11) 0.35270(9) 0.9571(4) 0.0462(7) Uani 1 1 d . . . C12 C 0.55546(14) 0.37654(13) 1.2179(5) 0.0735(12) Uani 1 1 d . . . H12C H 0.5270 0.3736 1.2810 0.110 Uiso 1 1 calc R . . H12D H 0.5725 0.3999 1.2576 0.110 Uiso 1 1 calc R . . H12E H 0.5744 0.3525 1.2312 0.110 Uiso 1 1 calc R . . C13 C 0.55750(18) 0.42037(13) 0.9620(6) 0.0987(17) Uani 1 1 d . . . H13A H 0.5605 0.4164 0.8435 0.148 Uiso 1 1 calc R . . H13B H 0.5870 0.4294 1.0071 0.148 Uiso 1 1 calc R . . H13C H 0.5339 0.4406 0.9834 0.148 Uiso 1 1 calc R . . Cl1 Cl 0.43044(3) 0.34665(3) 0.41216(11) 0.0581(2) Uani 1 1 d . . . Cl2 Cl 0.38892(3) 0.31751(3) 0.82101(12) 0.0648(2) Uani 1 1 d . . . Cl3 Cl 0.47550(3) 0.23283(2) 0.87676(11) 0.05112(18) Uani 1 1 d . . . O21 O 0.5000 0.0000 0.2436(12) 0.229(5) Uani 1 2 d S . . C21 C 0.5000 0.0000 0.0933(13) 0.106(2) Uani 1 2 d S . . C22 C 0.4989(2) 0.03841(14) -0.0044(9) 0.1062(17) Uani 1 1 d . . . H22A H 0.4669 0.0457 -0.0280 0.159 Uiso 1 1 calc R . . H22B H 0.5156 0.0347 -0.1075 0.159 Uiso 1 1 calc R . . H22C H 0.5135 0.0598 0.0590 0.159 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 Sb 0.04535(10) 0.04172(10) 0.03064(9) 0.00246(8) 0.00140(9) 0.00494(8) Se1 0.0599(2) 0.0728(2) 0.04328(19) -0.00651(17) 0.00876(17) -0.01754(17) N1 0.0657(18) 0.0578(17) 0.0513(18) -0.0093(14) 0.0073(15) -0.0195(13) N2 0.089(2) 0.0697(19) 0.0450(19) -0.0104(15) 0.0136(16) -0.0323(17) C1 0.0388(15) 0.0484(17) 0.0444(18) -0.0011(14) -0.0026(14) -0.0042(13) C2 0.102(3) 0.084(3) 0.060(3) -0.021(2) 0.001(2) -0.033(3) C3 0.177(5) 0.095(3) 0.081(4) -0.024(3) 0.045(4) -0.081(4) Se11 0.0947(3) 0.0604(2) 0.0429(2) 0.00960(17) -0.01213(19) -0.0256(2) N11 0.0598(17) 0.0546(17) 0.0464(17) 0.0010(14) -0.0073(14) -0.0182(13) N12 0.103(2) 0.0537(17) 0.0434(17) 0.0075(14) -0.0188(17) -0.0221(16) C11 0.0481(18) 0.0442(17) 0.0462(19) 0.0021(15) -0.0005(15) -0.0004(14) C12 0.083(3) 0.086(3) 0.052(2) -0.009(2) -0.013(2) -0.022(2) C13 0.143(4) 0.074(3) 0.078(3) 0.010(3) -0.024(3) -0.057(3) Cl1 0.0677(5) 0.0549(5) 0.0517(5) 0.0162(4) -0.0100(4) 0.0044(4) Cl2 0.0682(5) 0.0734(6) 0.0529(5) -0.0116(4) 0.0165(4) 0.0132(4) Cl3 0.0665(5) 0.0479(4) 0.0389(4) -0.0022(4) -0.0006(4) 0.0004(3) O21 0.404(15) 0.181(7) 0.101(6) 0.000 0.000 0.108(8) C21 0.114(6) 0.096(6) 0.108(7) 0.000 0.000 0.020(4) C22 0.120(4) 0.077(3) 0.121(5) -0.002(3) 0.011(4) 0.001(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 Sb Cl2 2.4112(8) . ? Sb Cl1 2.4504(8) . ? Sb Se11 2.8514(4) . ? Sb Se1 2.8908(4) . ? Se1 C1 1.882(3) . ? N1 C1 1.299(4) . ? N1 C3 1.451(5) . ? N1 C2 1.461(5) . ? N2 C1 1.319(4) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C2 H2C 0.9600 . ? C2 H2D 0.9600 . ? C2 H2E 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? Se11 C11 1.876(3) . ? N11 C11 1.317(4) . ? N11 C13 1.456(5) . ? N11 C12 1.467(4) . ? N12 C11 1.308(4) . ? N12 H12A 0.8600 . ? N12 H12B 0.8600 . ? C12 H12C 0.9600 . ? C12 H12D 0.9600 . ? C12 H12E 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O21 C21 1.203(12) . ? C21 C22 1.482(7) . ? C21 C22 1.482(7) 2_655 ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Sb Cl1 95.77(3) . . ? Cl2 Sb Se11 90.62(3) . . ? Cl1 Sb Se11 79.59(2) . . ? Cl2 Sb Se1 79.77(2) . . ? Cl1 Sb Se1 91.44(2) . . ? Se11 Sb Se1 166.185(14) . . ? C1 Se1 Sb 107.04(9) . . ? C1 N1 C3 122.4(3) . . ? C1 N1 C2 121.8(3) . . ? C3 N1 C2 115.7(3) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? N1 C1 N2 119.3(3) . . ? N1 C1 Se1 122.1(2) . . ? N2 C1 Se1 118.6(2) . . ? N1 C2 H2C 109.5 . . ? N1 C2 H2D 109.5 . . ? H2C C2 H2D 109.5 . . ? N1 C2 H2E 109.5 . . ? H2C C2 H2E 109.5 . . ? H2D C2 H2E 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C11 Se11 Sb 109.50(9) . . ? C11 N11 C13 122.1(3) . . ? C11 N11 C12 120.1(3) . . ? C13 N11 C12 117.7(3) . . ? C11 N12 H12A 120.0 . . ? C11 N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? N12 C11 N11 119.8(3) . . ? N12 C11 Se11 119.5(2) . . ? N11 C11 Se11 120.7(2) . . ? N11 C12 H12C 109.5 . . ? N11 C12 H12D 109.5 . . ? H12C C12 H12D 109.5 . . ? N11 C12 H12E 109.5 . . ? H12C C12 H12E 109.5 . . ? H12D C12 H12E 109.5 . . ? N11 C13 H13A 109.5 . . ? N11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O21 C21 C22 121.8(4) . . ? O21 C21 C22 121.8(4) . 2_655 ? C22 C21 C22 116.4(8) . 2_655 ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Sb Se1 C1 158.42(10) . . . . ? Cl1 Sb Se1 C1 62.81(10) . . . . ? Se11 Sb Se1 C1 111.88(11) . . . . ? C3 N1 C1 N2 175.5(4) . . . . ? C2 N1 C1 N2 -4.9(5) . . . . ? C3 N1 C1 Se1 -7.2(6) . . . . ? C2 N1 C1 Se1 172.4(3) . . . . ? Sb Se1 C1 N1 155.3(3) . . . . ? Sb Se1 C1 N2 -27.4(3) . . . . ? Cl2 Sb Se11 C11 60.93(10) . . . . ? Cl1 Sb Se11 C11 156.69(10) . . . . ? Se1 Sb Se11 C11 106.52(11) . . . . ? C13 N11 C11 N12 -178.6(4) . . . . ? C12 N11 C11 N12 2.4(5) . . . . ? C13 N11 C11 Se11 0.3(5) . . . . ? C12 N11 C11 Se11 -178.7(3) . . . . ? Sb Se11 C11 N12 10.3(3) . . . . ? Sb Se11 C11 N11 -168.6(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 N2 H2A Cl3 0.86 2.58 3.321(3) 144.8 1_554 N2 H2B Cl1 0.86 2.71 3.541(3) 161.5 . N12 H12A Cl3 0.86 2.50 3.250(3) 145.9 6_655 N12 H12B Cl3 0.86 2.43 3.254(3) 161.8 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.700 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.055