# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Andreas Lemmerer' _publ_contact_author_email ANDREAS.LEMMERER@GMAIL.COM _publ_section_title ; The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides ; _publ_requested_category FO loop_ _publ_author_name 'Andreas Lemmerer' 'Manuel A Fernandes' 'Marcus Layh' 'Demetrius C Levendis' 'Bernard Omondi' # Attachment 'Thioamide_cif.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-03-02 at 17:13:20 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : 6bbo13_s smart data_1 _database_code_depnum_ccdc_archive 'CCDC 710584' _audit_creation_date 2009-03-02T17:13:20-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,6-diflourophenylthioamide ; _chemical_formula_moiety 'C7 H5 F2 N S' _chemical_formula_sum 'C7 H5 F2 N S' _chemical_formula_weight 173.18 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 10.346(1) _cell_length_b 8.119(1) _cell_length_c 17.883(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1502.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 820 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 24.82 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Block _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.947 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_unetI/netI 0.0432 _diffrn_reflns_number 14956 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1813 _reflns_number_gt 1079 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0531P)^2^+0.9667P] 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_number_reflns 1813 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.348 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' F F 0.0171 0.0103 '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' 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 0.4484(2) 0.0116(3) 0.62859(12) 0.0326(6) Uani 1 1 d . . . C2 C 0.3852(3) 0.0983(3) 0.57202(15) 0.0428(7) Uani 1 1 d . . . C3 C 0.2523(3) 0.1015(4) 0.5662(2) 0.0598(9) Uani 1 1 d . . . H3 H 0.211 0.1604 0.527 0.072 Uiso 1 1 calc R . . C4 C 0.1807(3) 0.0163(4) 0.6190(2) 0.0682(12) Uani 1 1 d . . . H4 H 0.089 0.0175 0.6159 0.082 Uiso 1 1 calc R . . C5 C 0.2393(3) -0.0703(4) 0.67618(19) 0.0572(9) Uani 1 1 d . . . H5 H 0.189 -0.1266 0.7125 0.069 Uiso 1 1 calc R . . C6 C 0.3714(3) -0.0732(3) 0.67932(15) 0.0420(7) Uani 1 1 d . . . C7 C 0.6650(2) 0.1269(3) 0.63105(12) 0.0318(5) Uani 1 1 d . . . H7 H 0.6288 0.2344 0.6294 0.038 Uiso 1 1 calc R . . N1 N 0.58474(19) 0.0000(3) 0.63262(11) 0.0304(5) Uani 1 1 d . . . F1 F 0.45934(16) 0.1806(2) 0.52181(8) 0.0549(5) Uani 1 1 d . . . F2 F 0.43284(16) -0.1617(2) 0.73269(9) 0.0534(5) Uani 1 1 d . . . S1 S 0.82396(6) 0.10992(8) 0.63171(4) 0.0432(2) Uani 1 1 d . . . H1 H 0.617(3) -0.102(4) 0.6348(15) 0.052 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 C1 0.0288(12) 0.0314(14) 0.0377(12) -0.0108(11) 0.0011(10) 0.0023(10) C2 0.0399(15) 0.0399(16) 0.0485(15) -0.0164(13) -0.0073(12) 0.0100(13) C3 0.0429(17) 0.055(2) 0.081(2) -0.0337(18) -0.0252(17) 0.0200(16) C4 0.0260(15) 0.062(2) 0.117(3) -0.053(2) -0.0033(18) 0.0029(16) C5 0.0354(16) 0.056(2) 0.081(2) -0.0352(17) 0.0157(16) -0.0073(14) C6 0.0357(14) 0.0402(16) 0.0502(16) -0.0179(12) 0.0078(12) -0.0043(12) C7 0.0302(12) 0.0324(13) 0.0327(12) 0.0039(10) 0.0035(10) 0.0041(11) N1 0.0279(10) 0.0259(11) 0.0375(10) 0.0021(9) 0.0022(9) 0.0013(9) F1 0.0641(11) 0.0546(11) 0.0460(9) 0.0048(8) -0.0079(8) 0.0169(9) F2 0.0556(10) 0.0554(10) 0.0492(9) 0.0049(7) 0.0136(8) -0.0094(8) S1 0.0284(3) 0.0324(4) 0.0687(5) 0.0072(3) 0.0051(3) -0.0016(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.390(4) . ? C1 C2 1.395(3) . ? C1 N1 1.415(3) . ? C2 F1 1.357(3) . ? C2 C3 1.379(4) . ? C3 C4 1.386(5) . ? C3 H3 0.95 . ? C4 C5 1.380(5) . ? C4 H4 0.95 . ? C5 C6 1.368(4) . ? C5 H5 0.95 . ? C6 F2 1.354(3) . ? C7 N1 1.323(3) . ? C7 S1 1.651(2) . ? C7 H7 0.95 . ? N1 H1 0.89(3) . ? 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 C6 C1 C2 117.0(2) . . ? C6 C1 N1 120.3(2) . . ? C2 C1 N1 122.5(2) . . ? F1 C2 C3 120.3(3) . . ? F1 C2 C1 117.6(2) . . ? C3 C2 C1 122.1(3) . . ? C2 C3 C4 118.2(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 121.6(3) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 118.5(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? F2 C6 C5 120.5(3) . . ? F2 C6 C1 117.0(2) . . ? C5 C6 C1 122.5(3) . . ? N1 C7 S1 124.1(2) . . ? N1 C7 H7 118 . . ? S1 C7 H7 118 . . ? C7 N1 C1 124.9(2) . . ? C7 N1 H1 119(2) . . ? C1 N1 H1 116(2) . . ? 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 C6 C1 C2 F1 -179.5(2) . . . . ? N1 C1 C2 F1 -3.4(3) . . . . ? C6 C1 C2 C3 0.3(4) . . . . ? N1 C1 C2 C3 176.3(2) . . . . ? F1 C2 C3 C4 -179.7(2) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 F2 -177.5(2) . . . . ? C4 C5 C6 C1 2.0(4) . . . . ? C2 C1 C6 F2 177.9(2) . . . . ? N1 C1 C6 F2 1.7(3) . . . . ? C2 C1 C6 C5 -1.6(4) . . . . ? N1 C1 C6 C5 -177.7(2) . . . . ? S1 C7 N1 C1 -176.91(18) . . . . ? C6 C1 N1 C7 -131.6(2) . . . . ? C2 C1 N1 C7 52.4(3) . . . . ? 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 C4 H4 S1 0.95 2.86 3.775(3) 163 1_455 N1 H1 S1 0.89(3) 2.42(3) 3.305(2) 172(3) 7_755 C7 H7 S1 0.95 3.09 3.924(3) 148 7_765 _chemical_name_common 2,6-diflourophenylthioamide ###END data_2 _database_code_depnum_ccdc_archive 'CCDC 710585' _audit_creation_date 2009-03-02T17:18:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,6-dichlorophenylthioamide ; _chemical_formula_moiety 'C7 H5 Cl2 N S' _chemical_formula_sum 'C7 H5 Cl2 N S' _chemical_formula_weight 206.08 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.873(2) _cell_length_b 15.643(4) _cell_length_c 7.991(2) _cell_angle_alpha 90 _cell_angle_beta 117.336(5) _cell_angle_gamma 90 _cell_volume 874.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 721 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.24 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.911 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7717 _exptl_absorpt_correction_T_max 0.8831 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_number 5989 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2116 _reflns_number_gt 1583 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0296P)^2^+0.2418P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0125(13) _refine_ls_number_reflns 2116 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.255 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.7859(2) 0.44320(10) 0.0431(2) 0.0306(3) Uani 1 1 d . . . C2 C 0.9491(2) 0.46008(11) 0.2119(2) 0.0363(4) Uani 1 1 d . . . C3 C 1.0049(3) 0.54275(13) 0.2718(3) 0.0469(5) Uani 1 1 d . . . H3 H 1.1141 0.5531 0.389 0.056 Uiso 1 1 calc R . . C4 C 0.9016(3) 0.61021(13) 0.1611(3) 0.0501(5) Uani 1 1 d . . . H4 H 0.9394 0.6671 0.2035 0.06 Uiso 1 1 calc R . . C5 C 0.7440(3) 0.59640(11) -0.0109(3) 0.0416(4) Uani 1 1 d . . . H5 H 0.6759 0.6431 -0.0888 0.05 Uiso 1 1 calc R . . C6 C 0.6872(2) 0.51288(11) -0.0674(2) 0.0339(4) Uani 1 1 d . . . C7 C 0.6859(2) 0.30240(11) 0.0864(2) 0.0348(4) Uani 1 1 d . . . H7 H 0.7091 0.3201 0.2088 0.042 Uiso 1 1 calc R . . N1 N 0.7206(2) 0.35911(9) -0.0180(2) 0.0334(3) Uani 1 1 d . . . S1 S 0.60652(8) 0.20458(3) 0.02310(7) 0.04621(16) Uani 1 1 d . . . Cl1 Cl 1.09108(7) 0.37708(3) 0.34965(7) 0.05224(16) Uani 1 1 d . . . Cl2 Cl 0.48911(7) 0.49385(3) -0.28080(7) 0.04748(15) Uani 1 1 d . . . H1 H 0.696(3) 0.3458(14) -0.130(3) 0.057 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 C1 0.0371(9) 0.0303(8) 0.0291(8) -0.0015(6) 0.0191(7) 0.0002(7) C2 0.0364(9) 0.0395(10) 0.0331(9) -0.0004(7) 0.0162(8) 0.0004(8) C3 0.0433(11) 0.0489(12) 0.0452(11) -0.0123(9) 0.0175(9) -0.0093(9) C4 0.0568(13) 0.0350(10) 0.0641(14) -0.0118(9) 0.0325(11) -0.0099(9) C5 0.0485(11) 0.0297(9) 0.0538(12) 0.0013(8) 0.0298(10) 0.0031(8) C6 0.0385(10) 0.0341(9) 0.0332(9) 0.0011(7) 0.0199(8) 0.0018(7) C7 0.0393(10) 0.0355(9) 0.0294(8) 0.0017(7) 0.0158(8) 0.0032(7) N1 0.0444(8) 0.0287(7) 0.0264(7) -0.0011(6) 0.0157(7) 0.0003(6) S1 0.0650(3) 0.0304(2) 0.0409(3) 0.00068(19) 0.0222(2) -0.0049(2) Cl1 0.0467(3) 0.0554(3) 0.0411(3) 0.0073(2) 0.0085(2) 0.0075(2) Cl2 0.0530(3) 0.0458(3) 0.0338(2) 0.00488(19) 0.0114(2) 0.0094(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.393(2) . ? C1 C2 1.396(2) . ? C1 N1 1.415(2) . ? C2 C3 1.379(3) . ? C2 Cl1 1.737(2) . ? C3 C4 1.377(3) . ? C3 H3 0.95 . ? C4 C5 1.382(3) . ? C4 H4 0.95 . ? C5 C6 1.388(2) . ? C5 H5 0.95 . ? C6 Cl2 1.728(2) . ? C7 N1 1.330(2) . ? C7 S1 1.643(2) . ? C7 H7 0.95 . ? N1 H1 0.85(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 C6 C1 C2 117.6(2) . . ? C6 C1 N1 120.0(2) . . ? C2 C1 N1 122.5(2) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 Cl1 118.1(2) . . ? C1 C2 Cl1 120.7(1) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 118.6(2) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 121.9(2) . . ? C5 C6 Cl2 119.6(1) . . ? C1 C6 Cl2 118.6(1) . . ? N1 C7 S1 125.9(1) . . ? N1 C7 H7 117 . . ? S1 C7 H7 117 . . ? C7 N1 C1 123.4(1) . . ? C7 N1 H1 118.8(2) . . ? C1 N1 H1 117.7(2) . . ? 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 C6 C1 C2 C3 3.2(3) . . . . ? N1 C1 C2 C3 -177.28(16) . . . . ? C6 C1 C2 Cl1 -175.07(12) . . . . ? N1 C1 C2 Cl1 4.4(2) . . . . ? C1 C2 C3 C4 -1.9(3) . . . . ? Cl1 C2 C3 C4 176.43(15) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 2.3(3) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C4 C5 C6 Cl2 179.39(14) . . . . ? C2 C1 C6 C5 -1.9(2) . . . . ? N1 C1 C6 C5 178.66(16) . . . . ? C2 C1 C6 Cl2 177.92(13) . . . . ? N1 C1 C6 Cl2 -1.6(2) . . . . ? S1 C7 N1 C1 178.84(13) . . . . ? C6 C1 N1 C7 -126.38(18) . . . . ? C2 C1 N1 C7 54.2(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 N1 H1 S1 0.85(2) 2.65(2) 3.496(2) 176(2) 4_565 C7 H7 S1 0.95 3 3.819(2) 146 4_566 _chemical_name_common 2,6-dichlorophenylthioamide ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 710586' _audit_creation_date 2009-03-02T17:31:53-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,6-dibromophenylthioamide ; _chemical_formula_moiety 'C7 H5 Br2 N S' _chemical_formula_sum 'C7 H5 Br2 N S' _chemical_formula_weight 295 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.9801(5) _cell_length_b 8.0314(5) _cell_length_c 14.5984(9) _cell_angle_alpha 90 _cell_angle_beta 99.884(4) _cell_angle_gamma 90 _cell_volume 921.74(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1851 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.12 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.955 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.134 _exptl_absorpt_correction_T_max 0.70 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0534 _diffrn_reflns_number 6607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2216 _reflns_number_gt 1620 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0614P)^2^+0.7396P] 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_number_reflns 2216 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.131 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.124 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.3583(6) 0.6488(5) 0.8837(3) 0.0345(10) Uani 1 1 d . . . C2 C 0.3733(7) 0.7426(6) 0.9646(3) 0.0406(11) Uani 1 1 d . . . C3 C 0.5296(8) 0.7821(6) 1.0154(3) 0.0488(13) Uani 1 1 d . . . H3 H 0.5373 0.8491 1.0696 0.059 Uiso 1 1 calc R . . C4 C 0.6765(7) 0.7235(7) 0.9868(3) 0.0485(13) Uani 1 1 d . . . H4 H 0.785 0.752 1.021 0.058 Uiso 1 1 calc R . . C5 C 0.6648(7) 0.6252(6) 0.9099(3) 0.0438(11) Uani 1 1 d . . . H5 H 0.7649 0.583 0.8912 0.053 Uiso 1 1 calc R . . C6 C 0.5068(6) 0.5872(5) 0.8593(3) 0.0332(9) Uani 1 1 d . . . C7 C 0.0962(6) 0.7311(6) 0.7866(3) 0.0379(10) Uani 1 1 d . . . H7 H 0.1314 0.8432 0.7983 0.045 Uiso 1 1 calc R . . N1 N 0.1981(5) 0.6137(5) 0.8282(3) 0.0378(9) Uani 1 1 d . . . S1 S -0.08510(18) 0.70127(16) 0.71658(10) 0.0493(3) Uani 1 1 d . . . Br1 Br 0.17902(9) 0.81414(8) 1.01199(5) 0.0646(2) Uani 1 1 d . . . Br2 Br 0.49267(7) 0.45272(7) 0.75278(3) 0.0514(2) Uani 1 1 d . . . H1 H 0.170(8) 0.499(7) 0.816(4) 0.062 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 C1 0.041(3) 0.026(2) 0.037(2) 0.0032(17) 0.0054(19) -0.0026(19) C2 0.048(3) 0.037(2) 0.039(2) 0.0002(19) 0.012(2) 0.002(2) C3 0.061(4) 0.047(3) 0.036(2) -0.003(2) 0.000(2) -0.006(3) C4 0.044(3) 0.057(3) 0.039(2) 0.007(2) -0.009(2) -0.010(3) C5 0.037(3) 0.048(3) 0.046(3) 0.011(2) 0.006(2) -0.001(2) C6 0.041(3) 0.028(2) 0.031(2) 0.0031(16) 0.0063(18) 0.0013(19) C7 0.033(2) 0.035(2) 0.045(2) -0.0005(19) 0.0046(19) 0.000(2) N1 0.033(2) 0.0288(19) 0.049(2) -0.0022(17) 0.0002(17) -0.0009(17) S1 0.0391(7) 0.0465(7) 0.0572(8) 0.0026(6) -0.0060(6) 0.0020(6) Br1 0.0609(4) 0.0684(4) 0.0700(4) -0.0183(3) 0.0268(3) 0.0032(3) Br2 0.0556(4) 0.0477(3) 0.0531(3) -0.0147(2) 0.0154(2) -0.0017(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.385(6) . ? C1 C2 1.389(6) . ? C1 N1 1.420(6) . ? C2 C3 1.374(7) . ? C2 Br1 1.892(5) . ? C3 C4 1.392(8) . ? C3 H3 0.95 . ? C4 C5 1.363(7) . ? C4 H4 0.95 . ? C5 C6 1.382(7) . ? C5 H5 0.95 . ? C6 Br2 1.881(4) . ? C7 N1 1.323(6) . ? C7 S1 1.639(5) . ? C7 H7 0.95 . ? N1 H1 0.96(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 C6 C1 C2 117.4(4) . . ? C6 C1 N1 120.6(4) . . ? C2 C1 N1 122.1(4) . . ? C3 C2 C1 121.4(5) . . ? C3 C2 Br1 117.3(4) . . ? C1 C2 Br1 121.3(4) . . ? C2 C3 C4 119.6(5) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 120 . . ? C3 C4 H4 120 . . ? C4 C5 C6 119.7(5) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 121.8(4) . . ? C5 C6 Br2 119.2(4) . . ? C1 C6 Br2 119.0(3) . . ? N1 C7 S1 126.1(4) . . ? N1 C7 H7 117 . . ? S1 C7 H7 117 . . ? C7 N1 C1 122.9(4) . . ? C7 N1 H1 120(4) . . ? C1 N1 H1 117(4) . . ? 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 C6 C1 C2 C3 4.2(7) . . . . ? N1 C1 C2 C3 -176.9(4) . . . . ? C6 C1 C2 Br1 -173.5(3) . . . . ? N1 C1 C2 Br1 5.5(6) . . . . ? C1 C2 C3 C4 -1.8(8) . . . . ? Br1 C2 C3 C4 175.9(4) . . . . ? C2 C3 C4 C5 -1.1(8) . . . . ? C3 C4 C5 C6 1.4(7) . . . . ? C4 C5 C6 C1 1.1(7) . . . . ? C4 C5 C6 Br2 179.5(4) . . . . ? C2 C1 C6 C5 -3.8(6) . . . . ? N1 C1 C6 C5 177.2(4) . . . . ? C2 C1 C6 Br2 177.7(3) . . . . ? N1 C1 C6 Br2 -1.2(5) . . . . ? S1 C7 N1 C1 176.2(4) . . . . ? C6 C1 N1 C7 -118.6(5) . . . . ? C2 C1 N1 C7 62.6(6) . . . . ? 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 N1 H1 S1 0.96(6) 2.51(6) 3.465(4) 178(5) 2_546 C7 H7 S1 0.95 2.9 3.777(5) 154 2_556 C4 H4 S1 0.95 2.89 3.612(5) 134 4_676 _chemical_name_common 2,6-dibromophenylthioamide ###END data_4 _database_code_depnum_ccdc_archive 'CCDC 710587' _audit_creation_date 2009-03-02T17:41:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,6-dimethylphenylthioamide ; _chemical_formula_moiety 'C9 H11 N S' _chemical_formula_sum 'C9 H11 N S' _chemical_formula_weight 165.25 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.555(2) _cell_length_b 8.0597(13) _cell_length_c 16.133(3) _cell_angle_alpha 90 _cell_angle_beta 101.422(4) _cell_angle_gamma 90 _cell_volume 1855.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 628 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 23.064 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8775 _exptl_absorpt_correction_T_max 0.9831 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_unetI/netI 0.0653 _diffrn_reflns_number 6215 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2230 _reflns_number_gt 1253 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0502P)^2^+0.3281P] 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_number_reflns 2230 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.165 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.87318(15) 0.3543(2) 0.43529(12) 0.0369(5) Uani 1 1 d . . . C2 C 0.95664(16) 0.2655(3) 0.44578(14) 0.0486(6) Uani 1 1 d . . . C3 C 1.00356(18) 0.2357(3) 0.52854(16) 0.0616(7) Uani 1 1 d . . . H3 H 1.0601 0.1735 0.5382 0.074 Uiso 1 1 calc R . . C4 C 0.96929(19) 0.2950(4) 0.59623(15) 0.0646(7) Uani 1 1 d . . . H4 H 1.0024 0.2736 0.6521 0.077 Uiso 1 1 calc R . . C5 C 0.88768(18) 0.3850(3) 0.58382(14) 0.0530(6) Uani 1 1 d . . . H5 H 0.8652 0.426 0.6313 0.064 Uiso 1 1 calc R . . C6 C 0.83757(15) 0.4169(2) 0.50304(13) 0.0416(5) Uani 1 1 d . . . C7 C 0.78263(15) 0.2700(2) 0.29856(12) 0.0413(5) Uani 1 1 d . . . H7 H 0.7933 0.1585 0.317 0.05 Uiso 1 1 calc R . . C8 C 0.99817(19) 0.2065(3) 0.37220(17) 0.0673(7) Uani 1 1 d . . . H8A H 1.0647 0.1804 0.392 0.101 Uiso 1 1 calc R . . H8B H 0.9649 0.1069 0.3476 0.101 Uiso 1 1 calc R . . H8C H 0.9919 0.2939 0.3292 0.101 Uiso 1 1 calc R . . C9 C 0.74690(17) 0.5114(3) 0.48892(14) 0.0555(6) Uani 1 1 d . . . H9A H 0.7322 0.5419 0.5436 0.083 Uiso 1 1 calc R . . H9B H 0.6965 0.4418 0.4576 0.083 Uiso 1 1 calc R . . H9C H 0.7528 0.6121 0.4563 0.083 Uiso 1 1 calc R . . N1 N 0.82099(14) 0.3862(2) 0.35155(10) 0.0416(5) Uani 1 1 d . . . S1 S 0.71810(5) 0.29777(7) 0.20357(4) 0.0585(2) Uani 1 1 d . . . H1 H 0.8096(18) 0.486(3) 0.3379(15) 0.07 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 C1 0.0446(13) 0.0305(10) 0.0342(11) 0.0010(8) 0.0044(10) -0.0035(9) C2 0.0501(14) 0.0465(13) 0.0482(13) 0.0021(10) 0.0073(12) -0.0040(11) C3 0.0485(15) 0.0705(18) 0.0601(15) 0.0092(13) -0.0026(13) 0.0021(13) C4 0.0633(17) 0.0812(19) 0.0413(13) 0.0063(13) -0.0089(12) -0.0125(16) C5 0.0634(18) 0.0568(15) 0.0373(12) -0.0033(11) 0.0068(12) -0.0126(13) C6 0.0502(14) 0.0346(11) 0.0395(12) -0.0023(9) 0.0081(11) -0.0091(10) C7 0.0544(14) 0.0302(10) 0.0385(11) 0.0008(9) 0.0073(10) -0.0014(10) C8 0.0606(17) 0.0721(18) 0.0725(17) -0.0015(14) 0.0212(15) 0.0126(14) C9 0.0696(17) 0.0447(13) 0.0551(15) -0.0035(11) 0.0194(13) 0.0046(12) N1 0.0583(12) 0.0284(9) 0.0346(9) 0.0006(8) 0.0011(8) 0.0011(9) S1 0.0860(5) 0.0411(3) 0.0398(3) -0.0005(3) -0.0083(3) -0.0040(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.391(3) . ? C1 C6 1.394(3) . ? C1 N1 1.436(2) . ? C2 C3 1.395(3) . ? C2 C8 1.511(3) . ? C3 C4 1.373(3) . ? C3 H3 0.95 . ? C4 C5 1.372(4) . ? C4 H4 0.95 . ? C5 C6 1.386(3) . ? C5 H5 0.95 . ? C6 C9 1.501(3) . ? C7 N1 1.315(3) . ? C7 S1 1.646(2) . ? C7 H7 0.95 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? N1 H1 0.84(3) . ? 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 C2 C1 C6 122.84(19) . . ? C2 C1 N1 119.55(18) . . ? C6 C1 N1 117.60(18) . . ? C1 C2 C3 117.1(2) . . ? C1 C2 C8 122.8(2) . . ? C3 C2 C8 120.1(2) . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 121.0(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 117.5(2) . . ? C5 C6 C9 121.3(2) . . ? C1 C6 C9 121.13(19) . . ? N1 C7 S1 126.8(2) . . ? N1 C7 H7 116.6 . . ? S1 C7 H7 116.6 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 N1 C1 124.1(2) . . ? C7 N1 H1 118.3(2) . . ? C1 N1 H1 117.2(2) . . ? 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 C6 C1 C2 C3 1.9(3) . . . . ? N1 C1 C2 C3 -178.94(19) . . . . ? C6 C1 C2 C8 -176.2(2) . . . . ? N1 C1 C2 C8 2.9(3) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C8 C2 C3 C4 176.9(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 C9 178.4(2) . . . . ? C2 C1 C6 C5 -1.3(3) . . . . ? N1 C1 C6 C5 179.56(18) . . . . ? C2 C1 C6 C9 -179.7(2) . . . . ? N1 C1 C6 C9 1.2(3) . . . . ? S1 C7 N1 C1 177.06(17) . . . . ? C2 C1 N1 C7 63.9(3) . . . . ? C6 C1 N1 C7 -116.9(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 N1 H1 S1 0.84(3) 2.61(3) 3.452(2) 178(2) 4_655 C7 H7 S1 0.95 2.93 3.807(2) 154 4_645 C9 H9A S1 0.98 2.93 3.887(2) 166 6_566 _chemical_name_common 2,6-dimethylphenylthioamide ###END data_5 _database_code_depnum_ccdc_archive 'CCDC 710588' _audit_creation_date 2009-03-02T17:45:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-chloro-6-methylphenylthioamide ; _chemical_formula_moiety 'C8 H8 Cl N S' _chemical_formula_sum 'C8 H8 Cl N S' _chemical_formula_weight 185.66 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.3670(10) _cell_length_b 8.0220(10) _cell_length_c 16.0680(10) _cell_angle_alpha 90 _cell_angle_beta 100.9200(10) _cell_angle_gamma 90 _cell_volume 1818.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5886 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.16 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Irregular _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.9658 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.017 _diffrn_reflns_number 15652 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2197 _reflns_number_gt 1778 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, Bruker (1998)' _computing_cell_refinement 'Bruker SAINT+, Bruker (1999)' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0625P)^2^+2.2992P] 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_number_reflns 2197 _refine_ls_number_parameters 105 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.495 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.87420(14) 0.3542(2) 0.43580(12) 0.0376(4) Uani 1 1 d D A . C2 C 0.95805(15) 0.2660(2) 0.44961(12) 0.0470(5) Uani 1 1 d D . . C3 C 1.00633(18) 0.2362(3) 0.53071(18) 0.0604(7) Uani 1 1 d D A . H3 H 1.0639 0.1747 0.5396 0.072 Uiso 1 1 calc R . . C4 C 0.9710(2) 0.2956(4) 0.59882(16) 0.0621(7) Uani 1 1 d D . . H4 H 1.0037 0.2734 0.6548 0.075 Uiso 1 1 calc R A . C5 C 0.88852(18) 0.3871(3) 0.58624(14) 0.0526(6) Uani 1 1 d D A . H5 H 0.8651 0.4311 0.6332 0.063 Uiso 1 1 calc R . . C6 C 0.84055(11) 0.4140(2) 0.50507(13) 0.0413(5) Uani 1 1 d D . . C7 C 0.78639(16) 0.2658(3) 0.29918(13) 0.0406(5) Uani 1 1 d . A . H7 H 0.7996 0.154 0.3171 0.049 Uiso 1 1 calc R . . N1 N 0.82132(14) 0.3844(2) 0.35258(11) 0.0406(4) Uani 1 1 d . . . S1 S 0.72178(6) 0.29378(8) 0.20399(4) 0.0577(2) Uani 1 1 d . . . Cl1A Cl 1.00817(16) 0.1930(2) 0.36563(12) 0.0604(3) Uani 0.5 1 d PD A 1 C8A C 0.7540(5) 0.5115(11) 0.4864(5) 0.0604(3) Uani 0.5 1 d PD A 1 H8A H 0.7288 0.5272 0.5384 0.091 Uiso 0.5 1 calc PR A 1 H8B H 0.7071 0.4526 0.4443 0.091 Uiso 0.5 1 calc PR A 1 H8C H 0.7677 0.6203 0.4638 0.091 Uiso 0.5 1 calc PR A 1 C8B C 0.9990(7) 0.2149(11) 0.3751(5) 0.0604(3) Uani 0.5 1 d PD A 2 H8D H 0.9739 0.2868 0.3267 0.091 Uiso 0.5 1 calc PR A 2 H8E H 0.982 0.0988 0.3606 0.091 Uiso 0.5 1 calc PR A 2 H8F H 1.0682 0.2255 0.3889 0.091 Uiso 0.5 1 calc PR A 2 Cl1B Cl 0.73367(11) 0.5231(2) 0.49008(12) 0.0604(3) Uani 0.5 1 d PD A 2 H1 H 0.811(2) 0.486(4) 0.341(2) 0.072 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 C1 0.0455(11) 0.0315(9) 0.0342(9) 0.0013(8) 0.0039(8) -0.0037(8) C2 0.0472(12) 0.0473(12) 0.0461(12) 0.0005(10) 0.0076(10) -0.0004(10) C3 0.0468(14) 0.0720(18) 0.0577(14) 0.0088(13) -0.0018(11) 0.0057(12) C4 0.0607(16) 0.079(2) 0.0407(12) 0.0068(12) -0.0057(11) -0.0074(14) C5 0.0624(15) 0.0593(15) 0.0357(11) -0.0039(10) 0.0082(10) -0.0138(12) C6 0.0490(12) 0.0351(10) 0.0394(10) -0.0010(9) 0.0074(9) -0.0069(9) C7 0.0526(12) 0.0307(10) 0.0373(10) 0.0000(8) 0.0055(9) -0.0017(9) N1 0.0559(11) 0.0296(9) 0.0338(8) 0.0008(7) 0.0018(7) 0.0010(8) S1 0.0848(5) 0.0402(3) 0.0393(3) -0.0007(2) -0.0109(3) -0.0044(3) Cl1A 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5) C8A 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5) C8B 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5) Cl1B 0.0620(7) 0.0621(6) 0.0613(5) -0.0064(4) 0.0226(4) 0.0167(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.379(3) . ? C1 C6 1.381(3) . ? C1 N1 1.428(3) . ? C2 C3 1.376(3) . ? C2 C8B 1.488(8) . ? C2 Cl1A 1.746(1) . ? C3 C4 1.376(4) . ? C3 H3 0.95 . ? C4 C5 1.376(4) . ? C4 H4 0.95 . ? C5 C6 1.372(3) . ? C5 H5 0.95 . ? C6 C8A 1.451(8) . ? C6 Cl1B 1.745(1) . ? C7 N1 1.315(3) . ? C7 S1 1.647(2) . ? C7 H7 0.95 . ? N1 H1 0.84(3) . ? C8A H8A 0.98 . ? C8A H8B 0.98 . ? C8A H8C 0.98 . ? C8B H8D 0.98 . ? C8B H8E 0.98 . ? C8B H8F 0.98 . ? 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 C2 C1 C6 118.50(18) . . ? C2 C1 N1 122.09(18) . . ? C6 C1 N1 119.40(18) . . ? C3 C2 C1 120.66(18) . . ? C3 C2 C8B 120.6(4) . . ? C1 C2 C8B 118.6(4) . . ? C3 C2 Cl1A 117.8(2) . . ? C1 C2 Cl1A 121.56(18) . . ? C8B C2 Cl1A 3.9(4) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 119.2(2) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 121.50(18) . . ? C5 C6 C8A 122.5(4) . . ? C1 C6 C8A 115.9(4) . . ? C5 C6 Cl1B 118.73(19) . . ? C1 C6 Cl1B 119.76(16) . . ? C8A C6 Cl1B 4.9(4) . . ? N1 C7 S1 125.9(2) . . ? N1 C7 H7 117.1 . . ? S1 C7 H7 117.1 . . ? C7 N1 C1 123.9(2) . . ? C7 N1 H1 122(2) . . ? C1 N1 H1 114(2) . . ? C6 C8A H8A 109.5 . . ? C6 C8A H8B 109.5 . . ? C6 C8A H8C 109.5 . . ? C2 C8B H8D 109.5 . . ? C2 C8B H8E 109.5 . . ? H8D C8B H8E 109.5 . . ? C2 C8B H8F 109.5 . . ? H8D C8B H8F 109.5 . . ? H8E C8B H8F 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 C6 C1 C2 C3 0.90(18) . . . . ? N1 C1 C2 C3 -178.65(19) . . . . ? C6 C1 C2 C8B -174.5(4) . . . . ? N1 C1 C2 C8B 6.0(4) . . . . ? C6 C1 C2 Cl1A -177.45(18) . . . . ? N1 C1 C2 Cl1A 3.0(2) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C8B C2 C3 C4 174.9(4) . . . . ? Cl1A C2 C3 C4 178.1(2) . . . . ? C2 C3 C4 C5 -1.1(4) . . . . ? C3 C4 C5 C6 1.9(4) . . . . ? C4 C5 C6 C1 -1.4(4) . . . . ? C4 C5 C6 C8A -178.9(5) . . . . ? C4 C5 C6 Cl1B 177.5(2) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? N1 C1 C6 C5 179.5(2) . . . . ? C2 C1 C6 C8A 177.7(4) . . . . ? N1 C1 C6 C8A -2.8(5) . . . . ? C2 C1 C6 Cl1B -178.92(15) . . . . ? N1 C1 C6 Cl1B 0.6(3) . . . . ? S1 C7 N1 C1 177.65(17) . . . . ? C2 C1 N1 C7 60.2(3) . . . . ? C6 C1 N1 C7 -119.3(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 N1 H1 S1 0.84(3) 2.60(4) 3.433(2) 176(3) 4_655 C7 H7 S1 0.95 2.92 3.789(2) 153 4_645 ###END _chemical_name_common 2-chloro-6-methylphenylthioamide