data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Brindaban Ranu' _publ_contact_author_email OCBCR@IACS.RES.IN _publ_section_title ; One-pot copper nanoparticles-catalyzed green synthesis of S-aryl- and S-vinyl dithiocarbamates in water: high diastereoselectivity achieved for vinyl dithiocarbamates ; loop_ _publ_author_name 'Brindaban Ranu' 'Sukalyan Bhadra' 'Amit Saha' # Attachment 'SB_F1.cif' data_sb _database_code_depnum_ccdc_archive 'CCDC 684382' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl N S2' _chemical_formula_weight 297.85 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' 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 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 10.704(3) _cell_length_b 15.143(4) _cell_length_c 8.924(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.006(3) _cell_angle_gamma 90.00 _cell_volume 1424.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.543 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8541 _exptl_absorpt_correction_T_max 0.9579 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9909 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2504 _reflns_number_gt 2229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0596P)^2^+0.3964P] 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 2504 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _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 Cl1 Cl 0.10396(5) -0.39756(3) 0.22019(6) 0.03346(17) Uani 1 1 d . . . S1 S 0.22482(4) 0.14194(3) 0.00562(5) 0.02422(16) Uani 1 1 d . . . S2 S 0.50094(4) 0.12919(3) 0.14561(5) 0.02389(16) Uani 1 1 d . . . C1 C 0.12671(17) -0.28443(12) 0.1991(2) 0.0238(4) Uani 1 1 d . . . C2 C 0.05258(17) -0.22502(12) 0.2629(2) 0.0265(4) Uani 1 1 d . . . C3 C 0.06937(18) -0.13568(12) 0.2402(2) 0.0254(4) Uani 1 1 d . . . C4 C 0.15858(17) -0.10491(12) 0.1548(2) 0.0223(4) Uani 1 1 d . . . C5 C 0.23337(17) -0.16721(12) 0.0955(2) 0.0235(4) Uani 1 1 d . . . C6 C 0.21838(17) -0.25658(12) 0.1180(2) 0.0248(4) Uani 1 1 d . . . C7 C 0.16685(18) -0.00967(12) 0.1272(2) 0.0246(4) Uani 1 1 d . . . C8 C 0.24981(18) 0.03072(11) 0.0557(2) 0.0234(4) Uani 1 1 d . . . C9 C 0.37933(17) 0.18935(11) 0.05741(19) 0.0213(4) Uani 1 1 d . . . N10 N 0.38427(14) 0.27415(10) 0.01812(17) 0.0235(3) Uani 1 1 d . . . C11 C 0.27512(18) 0.32708(12) -0.0560(2) 0.0250(4) Uani 1 1 d . . . C12 C 0.23939(19) 0.39405(13) 0.0562(2) 0.0296(4) Uani 1 1 d . . . C13 C 0.3526(2) 0.45271(14) 0.1162(3) 0.0371(5) Uani 1 1 d . . . C14 C 0.46819(19) 0.39764(13) 0.1815(2) 0.0298(4) Uani 1 1 d . . . C15 C 0.49787(17) 0.32900(12) 0.0684(2) 0.0233(4) Uani 1 1 d . . . H2 H -0.0176(15) -0.2524(9) 0.3277(17) 0.000(3) Uiso 1 1 d . . . H3 H 0.021(2) -0.0943(13) 0.283(2) 0.025(5) Uiso 1 1 d . . . H5 H 0.295(2) -0.1495(13) 0.043(2) 0.026(5) Uiso 1 1 d . . . H6 H 0.269(2) -0.2968(15) 0.072(2) 0.037(6) Uiso 1 1 d . . . H7 H 0.107(2) 0.0246(14) 0.160(2) 0.032(6) Uiso 1 1 d . . . H8 H 0.3124(19) 0.0050(13) 0.015(2) 0.020(5) Uiso 1 1 d . . . H11A H 0.2063(19) 0.2895(13) -0.092(2) 0.021(5) Uiso 1 1 d . . . H11B H 0.301(2) 0.3578(12) -0.142(2) 0.024(5) Uiso 1 1 d . . . H12A H 0.214(2) 0.3603(13) 0.144(3) 0.030(6) Uiso 1 1 d . . . H12B H 0.170(2) 0.4273(15) 0.002(3) 0.042(6) Uiso 1 1 d . . . H13A H 0.332(2) 0.4893(16) 0.191(3) 0.047(7) Uiso 1 1 d . . . H13B H 0.369(2) 0.4863(14) 0.029(3) 0.032(6) Uiso 1 1 d . . . H14A H 0.453(2) 0.3667(14) 0.274(3) 0.038(6) Uiso 1 1 d . . . H14B H 0.541(2) 0.4341(14) 0.210(2) 0.029(5) Uiso 1 1 d . . . H15A H 0.5652(19) 0.2906(12) 0.112(2) 0.020(5) Uiso 1 1 d . . . H15B H 0.5162(19) 0.3569(12) -0.022(2) 0.022(5) 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 Cl1 0.0285(3) 0.0247(3) 0.0484(3) 0.0046(2) 0.0103(2) -0.00288(18) S1 0.0203(3) 0.0230(3) 0.0280(3) 0.00061(17) 0.0003(2) -0.00232(17) S2 0.0205(3) 0.0257(3) 0.0253(3) 0.00289(17) 0.0037(2) 0.00237(17) C1 0.0176(9) 0.0243(9) 0.0274(9) 0.0024(7) -0.0018(7) -0.0014(7) C2 0.0174(9) 0.0323(10) 0.0302(10) 0.0016(8) 0.0051(8) -0.0004(8) C3 0.0182(9) 0.0302(10) 0.0284(11) -0.0005(8) 0.0058(8) 0.0020(8) C4 0.0161(9) 0.0275(9) 0.0221(10) -0.0006(7) -0.0001(7) -0.0012(7) C5 0.0168(9) 0.0282(9) 0.0264(10) 0.0007(7) 0.0062(8) -0.0023(7) C6 0.0185(9) 0.0279(9) 0.0281(10) -0.0008(8) 0.0039(8) 0.0029(7) C7 0.0215(9) 0.0256(9) 0.0266(10) -0.0033(7) 0.0043(8) 0.0018(8) C8 0.0221(10) 0.0229(9) 0.0248(10) -0.0030(7) 0.0025(8) -0.0012(7) C9 0.0214(9) 0.0248(9) 0.0178(9) -0.0015(7) 0.0039(7) -0.0015(7) N10 0.0216(8) 0.0229(7) 0.0252(8) 0.0014(6) 0.0019(7) -0.0012(6) C11 0.0230(10) 0.0249(9) 0.0255(10) 0.0026(8) -0.0003(8) -0.0012(8) C12 0.0216(10) 0.0317(10) 0.0349(12) -0.0021(9) 0.0034(9) 0.0021(8) C13 0.0280(11) 0.0324(11) 0.0503(14) -0.0149(10) 0.0049(10) 0.0004(9) C14 0.0225(10) 0.0342(10) 0.0323(11) -0.0074(9) 0.0035(9) -0.0053(9) C15 0.0190(9) 0.0242(9) 0.0269(10) 0.0024(8) 0.0046(8) -0.0025(8) _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 Cl1 C1 1.7451(18) . ? S1 C8 1.7512(19) . ? S1 C9 1.7885(18) . ? S2 C9 1.6697(18) . ? C1 C6 1.382(3) . ? C1 C2 1.386(3) . ? C2 C3 1.384(3) . ? C2 H2 1.105(15) . ? C3 C4 1.401(3) . ? C3 H3 0.93(2) . ? C4 C5 1.399(3) . ? C4 C7 1.468(3) . ? C5 C6 1.381(3) . ? C5 H5 0.92(2) . ? C6 H6 0.96(2) . ? C7 C8 1.329(3) . ? C7 H7 0.91(2) . ? C8 H8 0.90(2) . ? C9 N10 1.335(2) . ? N10 C11 1.475(2) . ? N10 C15 1.477(2) . ? C11 C12 1.520(3) . ? C11 H11A 0.94(2) . ? C11 H11B 0.98(2) . ? C12 C13 1.522(3) . ? C12 H12A 1.01(2) . ? C12 H12B 0.96(3) . ? C13 C14 1.522(3) . ? C13 H13A 0.93(3) . ? C13 H13B 0.97(2) . ? C14 C15 1.521(3) . ? C14 H14A 0.99(2) . ? C14 H14B 0.95(2) . ? C15 H15A 0.95(2) . ? C15 H15B 0.96(2) . ? 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 C8 S1 C9 103.10(9) . . ? C6 C1 C2 121.77(17) . . ? C6 C1 Cl1 118.75(14) . . ? C2 C1 Cl1 119.48(14) . . ? C3 C2 C1 118.41(17) . . ? C3 C2 H2 124.1(8) . . ? C1 C2 H2 117.5(8) . . ? C2 C3 C4 121.54(17) . . ? C2 C3 H3 120.0(12) . . ? C4 C3 H3 118.4(12) . . ? C5 C4 C3 118.04(17) . . ? C5 C4 C7 122.96(16) . . ? C3 C4 C7 118.97(16) . . ? C6 C5 C4 121.15(17) . . ? C6 C5 H5 118.2(12) . . ? C4 C5 H5 120.6(12) . . ? C5 C6 C1 119.05(17) . . ? C5 C6 H6 118.2(13) . . ? C1 C6 H6 122.6(13) . . ? C8 C7 C4 126.66(17) . . ? C8 C7 H7 117.2(13) . . ? C4 C7 H7 116.1(13) . . ? C7 C8 S1 118.69(15) . . ? C7 C8 H8 126.7(12) . . ? S1 C8 H8 113.8(12) . . ? N10 C9 S2 125.84(14) . . ? N10 C9 S1 113.29(13) . . ? S2 C9 S1 120.87(10) . . ? C9 N10 C11 125.18(15) . . ? C9 N10 C15 121.97(15) . . ? C11 N10 C15 112.14(15) . . ? N10 C11 C12 109.74(16) . . ? N10 C11 H11A 109.7(11) . . ? C12 C11 H11A 110.9(12) . . ? N10 C11 H11B 107.3(12) . . ? C12 C11 H11B 109.7(11) . . ? H11A C11 H11B 109.4(17) . . ? C11 C12 C13 110.17(16) . . ? C11 C12 H12A 107.7(12) . . ? C13 C12 H12A 109.4(13) . . ? C11 C12 H12B 106.3(14) . . ? C13 C12 H12B 111.9(14) . . ? H12A C12 H12B 111.3(19) . . ? C12 C13 C14 111.07(17) . . ? C12 C13 H13A 109.2(16) . . ? C14 C13 H13A 109.3(16) . . ? C12 C13 H13B 105.3(13) . . ? C14 C13 H13B 110.4(13) . . ? H13A C13 H13B 112(2) . . ? C13 C14 C15 111.70(17) . . ? C13 C14 H14A 110.0(14) . . ? C15 C14 H14A 108.4(13) . . ? C13 C14 H14B 111.0(12) . . ? C15 C14 H14B 108.5(12) . . ? H14A C14 H14B 107.2(19) . . ? N10 C15 C14 109.28(15) . . ? N10 C15 H15A 107.7(11) . . ? C14 C15 H15A 112.3(11) . . ? N10 C15 H15B 105.7(12) . . ? C14 C15 H15B 110.7(11) . . ? H15A C15 H15B 111.0(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.412 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.055