# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Rosana Mariel Romano' 'A. Downs' 'Simon Parsons' 'Caroline Smith' 'Carlos O Della Vedova' _publ_contact_author_name 'Dr Rosana Mariel Romano' _publ_contact_author_address ; Dept of Chemistry CEQUINOR CC 962 La Plata Buenos Aires 1900 ARGENTINA ; _publ_contact_author_email ROMANO@QUIMICA.UNLP.EDU.AR _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Structural and Vibrational Properties of ClC(O)SY Compounds with Y = Cl and CH3 ; data_mecosc _database_code_CSD 200120 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H3 Cl O S' _chemical_formula_sum 'C2 H3 Cl O S' _chemical_formula_weight 110.55 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 6.1174(7) _cell_length_b 6.6674(7) _cell_length_c 11.3145(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 461.49(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 72 _cell_measurement_theta_min 14 _cell_measurement_theta_max 16 _exptl_crystal_description cylinder _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 1.099 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Omega-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2644 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.06 _reflns_number_total 446 _reflns_number_gt 427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; #========================================================================== == # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: mecosc # Data From: mecosc.cif - Data Type: CIF Bond Precision O- C = 0.0020 A # # CELL 0.71073 6.117 6.667 11.314 90.00 90.00 90.00 461.49 # SpaceGroup from Symmetry Pnma Hall: -P 2ac 2n # Reported Pnma -P 2ac 2n # MoietyFormula C2 H3 Cl O S # Reported C2 H3 Cl O S # SumFormula C2 H3 Cl O S # Reported C2 H3 Cl O S # Mr = 110.56[Calc], 110.55[Rep] # Dx,gcm-3 = 1.591[Calc], 1.591[Rep] # Z = 4[Calc], 4[Rep] # Mu (mm-1) = 1.099[Calc], 1.099[Rep] # F000 = 224.0[Calc], 224.0[Rep] # Calculated T limits: Tmin=0.651 Tmin'=0.651 Tmax=0.659 # Reported Hmax= 7, Kmax= 7, Lmax= 13, Nref= 446 , Th(max)= 25.06 # Calculated Hmax= 7, Kmax= 7, Lmax= 13, Nref= 446( 446), Ratio= 1.00( 1.00) # R= 0.0181( 427), wR2= 0.0466( 446), S = 1.120, Npar= 39 #========================================================================== == !! Congratulations !! :No (Serious) ALERT Situations were Detected #========================================================================== == I didn't think this EVER happened. ; _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^)+(0.0222P)^2^+0.1015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difamp _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.051(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 446 _refine_ls_number_parameters 39 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0181 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0460 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 C1 C 0.0873(4) 0.2500 0.36259(18) 0.0415(5) Uani 1 2 d S . . H1 H 0.146(3) 0.361(3) 0.3277(13) 0.061(5) Uiso 1 1 d . . . H2 H -0.065(5) 0.2500 0.355(2) 0.076(8) Uiso 1 2 d S . . S1 S 0.14658(7) 0.2500 0.51823(4) 0.0386(2) Uani 1 2 d S . . O2 O 0.5442(2) 0.2500 0.43059(13) 0.0500(4) Uani 1 2 d S . . C2 C 0.4281(3) 0.2500 0.51296(16) 0.0326(4) Uani 1 2 d S . . Cl1 Cl 0.53760(8) 0.2500 0.65930(4) 0.0505(2) Uani 1 2 d S . . 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 C1 0.0324(10) 0.0545(13) 0.0375(10) 0.000 -0.0025(8) 0.000 S1 0.0250(3) 0.0572(3) 0.0336(3) 0.000 0.00432(17) 0.000 O2 0.0293(7) 0.0728(10) 0.0479(8) 0.000 0.0078(6) 0.000 C2 0.0298(9) 0.0283(9) 0.0397(9) 0.000 -0.0002(8) 0.000 Cl1 0.0481(3) 0.0568(4) 0.0467(3) 0.000 -0.0159(2) 0.000 _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 C1 S1 1.798(2) . ? C1 H1 0.912(17) . ? C1 H2 0.94(3) . ? S1 C2 1.7233(18) . ? O2 C2 1.172(2) . ? C2 Cl1 1.7860(19) . ? 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 S1 C1 H1 110.1(10) . . ? S1 C1 H2 106.8(17) . . ? H1 C1 H2 110.5(13) . . ? C2 S1 C1 99.65(10) . . ? O2 C2 S1 129.29(16) . . ? O2 C2 Cl1 120.66(15) . . ? S1 C2 Cl1 110.04(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.172 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.034 data_clcosc _database_code_CSD 200121 #Note to referee: please see refine special details for checkcif output. _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C Cl2 O S' _chemical_formula_sum 'C Cl2 O S' _chemical_formula_weight 130.97 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 6.034(3) _cell_length_b 10.311(6) _cell_length_c 7.226(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.72(6) _cell_angle_gamma 90.00 _cell_volume 443.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 15 _cell_measurement_theta_max 16 _exptl_crystal_description cylinder _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.963 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 1.744 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 Omega-2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 48 _diffrn_reflns_number 2640 _diffrn_reflns_av_R_equivalents 0.1613 _diffrn_reflns_av_sigmaI/netI 0.0941 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 25.02 _reflns_number_total 771 _reflns_number_gt 565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; 020_ALERT B Large R(int) ................................. 0.16 The crystal decayed by 48% during data collection #========================================================================== 040_ALERT C No H-atoms in this Carbon containing compound ? There aren't any. 150_ALERT C Volume as Calculated Differs from that Given = 443.20 Ang-3 Rounding error? 790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 1 C Cl2 O S No action ; _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^+0.2773P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 771 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0956 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1859 _refine_ls_wR_factor_gt 0.1650 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 Cl2 Cl 0.4014(3) 0.80573(17) -0.0167(3) 0.0386(6) Uani 1 1 d . . . Cl1 Cl -0.2454(3) 0.95582(17) -0.3514(2) 0.0359(6) Uani 1 1 d . . . S1 S 0.1993(3) 0.93756(16) -0.1634(2) 0.0310(6) Uani 1 1 d . . . O1 O -0.0849(9) 0.7393(5) -0.1976(9) 0.0534(16) Uani 1 1 d . . . C1 C -0.0451(11) 0.8472(6) -0.2276(9) 0.0280(14) Uani 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 Cl2 0.0324(10) 0.0374(11) 0.0450(11) 0.0082(8) 0.0034(8) 0.0072(7) Cl1 0.0299(10) 0.0321(10) 0.0442(10) 0.0034(7) 0.0019(8) 0.0021(7) S1 0.0279(9) 0.0224(9) 0.0419(11) 0.0025(7) 0.0038(8) -0.0022(7) O1 0.038(3) 0.023(3) 0.096(4) 0.010(3) 0.002(3) -0.009(2) C1 0.029(3) 0.023(3) 0.033(3) -0.002(3) 0.007(3) 0.000(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 Cl2 S1 2.006(3) . ? Cl1 C1 1.775(7) . ? S1 C1 1.740(7) . ? O1 C1 1.166(8) . ? 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 C1 S1 Cl2 101.0(2) . . ? O1 C1 S1 130.8(6) . . ? O1 C1 Cl1 123.5(5) . . ? S1 C1 Cl1 105.7(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.780 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.171