# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hugo Tlahuext' _publ_contact_author_email tlahuext@uaem.mx loop_ _publ_author_name H.Tlahuext G.Navarrete-Vasquez # Attachment 'Compound 1.CIF' data_tiazol1 _database_code_depnum_ccdc_archive 'CCDC 827868' #TrackingRef 'Compound 1.CIF' _audit_update_record ; 2011-10-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,3-benzothiazole-2-yl _chemical_melting_point 408 _chemical_formula_moiety 'C17 H15 Cl N2 O2 S' _chemical_formula_sum 'C17 H15 Cl N2 O2 S' _chemical_formula_weight 346.82 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' 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 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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.097(3) _cell_length_b 10.088(2) _cell_length_c 26.807(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3271.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2868 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9063 _exptl_absorpt_correction_T_max 0.9261 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 27083 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2868 _reflns_number_gt 2830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0098P)^2^+5.1839P] 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 2868 _refine_ls_number_parameters 213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.318 _refine_ls_restrained_S_all 1.318 _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 C1 C 0.3689(2) 0.8177(3) 0.53947(10) 0.0184(6) Uani 1 1 d . . . C2 C 0.4189(2) 0.7071(3) 0.51929(10) 0.0215(6) Uani 1 1 d . . . H2 H 0.4778 0.6653 0.5367 0.026 Uiso 1 1 calc R . . C3 C 0.3846(2) 0.6566(3) 0.47415(10) 0.0256(7) Uani 1 1 d . . . H3 H 0.4197 0.5808 0.4603 0.031 Uiso 1 1 calc R . . C4 C 0.2988(2) 0.7174(3) 0.44929(10) 0.0253(6) Uani 1 1 d . . . C5 C 0.2485(2) 0.8282(3) 0.46875(10) 0.0271(6) Uani 1 1 d . . . H5 H 0.1899 0.8698 0.4511 0.033 Uiso 1 1 calc R . . C6 C 0.2832(2) 0.8792(3) 0.51417(10) 0.0237(6) Uani 1 1 d . . . H6 H 0.2486 0.9556 0.5278 0.028 Uiso 1 1 calc R . . C7 C 0.3994(2) 0.9902(3) 0.60291(10) 0.0193(6) Uani 1 1 d . . . C8 C 0.2800(2) 1.0206(3) 0.61799(9) 0.0171(6) Uani 1 1 d . . . C9 C 0.4425(2) 1.0911(3) 0.56571(11) 0.0269(7) Uani 1 1 d . . . H9A H 0.5169 1.0655 0.5549 0.040 Uiso 1 1 calc R . . H9B H 0.4452 1.1787 0.5814 0.040 Uiso 1 1 calc R . . H9C H 0.3932 1.0941 0.5367 0.040 Uiso 1 1 calc R . . C10 C 0.4682(2) 0.9922(3) 0.65023(11) 0.0254(6) Uani 1 1 d . . . H10A H 0.4459 0.9184 0.6718 0.038 Uiso 1 1 calc R . . H10B H 0.4564 1.0762 0.6678 0.038 Uiso 1 1 calc R . . H10C H 0.5466 0.9831 0.6417 0.038 Uiso 1 1 calc R . . C11 C 0.1169(2) 0.9268(2) 0.65682(9) 0.0162(5) Uani 1 1 d . . . C12 C -0.0279(2) 0.8655(3) 0.70029(9) 0.0176(6) Uani 1 1 d . . . C13 C -0.0605(2) 0.9959(3) 0.68973(9) 0.0191(6) Uani 1 1 d . . . C14 C -0.1608(2) 1.0461(3) 0.70652(10) 0.0254(6) Uani 1 1 d . . . H14 H -0.1826 1.1344 0.6991 0.030 Uiso 1 1 calc R . . C15 C -0.2275(2) 0.9636(3) 0.73419(10) 0.0255(6) Uani 1 1 d . . . H15 H -0.2969 0.9953 0.7457 0.031 Uiso 1 1 calc R . . C16 C -0.1954(2) 0.8342(3) 0.74574(10) 0.0221(6) Uani 1 1 d . . . H16 H -0.2423 0.7798 0.7654 0.027 Uiso 1 1 calc R . . C17 C -0.0960(2) 0.7848(3) 0.72879(10) 0.0203(6) Uani 1 1 d . . . H17 H -0.0745 0.6966 0.7365 0.024 Uiso 1 1 calc R . . Cl1 Cl 0.25506(7) 0.65567(9) 0.39190(3) 0.0394(2) Uani 1 1 d . . . N1 N 0.21932(18) 0.9158(2) 0.63421(8) 0.0177(5) Uani 1 1 d D . . H1 H 0.244(2) 0.8361(11) 0.6323(11) 0.027 Uiso 1 1 d D . . N2 N 0.07385(18) 0.8284(2) 0.68039(8) 0.0178(5) Uani 1 1 d . . . O1 O 0.40923(15) 0.85530(17) 0.58533(7) 0.0196(4) Uani 1 1 d . . . O2 O 0.24337(15) 1.13310(17) 0.61846(7) 0.0210(4) Uani 1 1 d . . . S1 S 0.04135(6) 1.07511(6) 0.65493(2) 0.01969(17) 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 C1 0.0187(13) 0.0170(13) 0.0196(14) 0.0020(11) 0.0038(11) -0.0040(11) C2 0.0230(14) 0.0169(14) 0.0246(15) 0.0020(11) 0.0042(12) -0.0008(11) C3 0.0354(16) 0.0156(14) 0.0260(15) -0.0018(12) 0.0095(13) -0.0006(12) C4 0.0284(15) 0.0276(16) 0.0199(14) -0.0029(12) 0.0042(12) -0.0107(12) C5 0.0226(14) 0.0356(17) 0.0232(14) 0.0028(13) 0.0019(12) 0.0004(13) C6 0.0259(15) 0.0245(15) 0.0206(14) -0.0014(12) 0.0056(12) 0.0056(12) C7 0.0216(14) 0.0122(13) 0.0242(14) -0.0012(11) 0.0032(11) -0.0030(11) C8 0.0239(14) 0.0134(14) 0.0141(13) -0.0001(10) -0.0018(10) -0.0017(11) C9 0.0268(15) 0.0185(14) 0.0354(17) 0.0037(13) 0.0079(13) -0.0021(12) C10 0.0223(14) 0.0252(15) 0.0287(16) -0.0049(12) -0.0024(12) -0.0001(12) C11 0.0193(13) 0.0145(13) 0.0148(12) -0.0011(11) -0.0011(10) 0.0009(11) C12 0.0199(14) 0.0178(13) 0.0152(13) -0.0035(11) -0.0029(11) -0.0007(11) C13 0.0226(14) 0.0199(14) 0.0146(13) 0.0008(11) 0.0000(10) -0.0013(11) C14 0.0292(15) 0.0239(15) 0.0231(14) 0.0004(12) 0.0068(12) 0.0074(12) C15 0.0231(15) 0.0307(16) 0.0225(14) -0.0053(12) 0.0035(12) 0.0036(12) C16 0.0253(15) 0.0245(15) 0.0166(13) -0.0030(11) 0.0027(11) -0.0067(12) C17 0.0230(14) 0.0198(14) 0.0180(13) -0.0023(11) 0.0008(11) -0.0023(11) Cl1 0.0491(5) 0.0451(5) 0.0239(4) -0.0102(3) 0.0003(4) -0.0088(4) N1 0.0212(12) 0.0119(11) 0.0201(11) 0.0009(9) 0.0032(9) 0.0016(9) N2 0.0208(11) 0.0147(11) 0.0180(11) -0.0012(9) 0.0007(9) -0.0016(9) O1 0.0239(10) 0.0152(9) 0.0196(9) -0.0006(8) -0.0007(8) 0.0015(8) O2 0.0224(10) 0.0131(10) 0.0274(10) 0.0022(8) 0.0014(8) -0.0018(8) S1 0.0239(3) 0.0144(3) 0.0208(3) 0.0019(3) 0.0048(3) 0.0032(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 C1 O1 1.376(3) . ? C1 C2 1.379(4) . ? C1 C6 1.385(4) . ? C2 C3 1.377(4) . ? C2 H2 0.9500 . ? C3 C4 1.378(4) . ? C3 H3 0.9500 . ? C4 C5 1.375(4) . ? C4 Cl1 1.742(3) . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.445(3) . ? C7 C9 1.517(4) . ? C7 C10 1.517(4) . ? C7 C8 1.530(4) . ? C8 O2 1.219(3) . ? C8 N1 1.359(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N2 1.287(3) . ? C11 N1 1.384(3) . ? C11 S1 1.753(3) . ? C12 C17 1.388(4) . ? C12 N2 1.393(3) . ? C12 C13 1.402(4) . ? C13 C14 1.390(4) . ? C13 S1 1.740(3) . ? C14 C15 1.376(4) . ? C14 H14 0.9500 . ? C15 C16 1.397(4) . ? C15 H15 0.9500 . ? C16 C17 1.378(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N1 H1 0.8600(11) . ? 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 O1 C1 C2 114.7(2) . . ? O1 C1 C6 125.4(2) . . ? C2 C1 C6 119.9(3) . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.2(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.8(3) . . ? C5 C4 Cl1 119.4(2) . . ? C3 C4 Cl1 119.8(2) . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.4(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O1 C7 C9 112.9(2) . . ? O1 C7 C10 103.8(2) . . ? C9 C7 C10 110.6(2) . . ? O1 C7 C8 110.6(2) . . ? C9 C7 C8 111.4(2) . . ? C10 C7 C8 107.1(2) . . ? O2 C8 N1 121.6(2) . . ? O2 C8 C7 122.2(2) . . ? N1 C8 C7 116.0(2) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 N1 121.0(2) . . ? N2 C11 S1 117.5(2) . . ? N1 C11 S1 121.52(19) . . ? C17 C12 N2 125.3(2) . . ? C17 C12 C13 119.6(2) . . ? N2 C12 C13 115.0(2) . . ? C14 C13 C12 121.5(3) . . ? C14 C13 S1 128.6(2) . . ? C12 C13 S1 109.9(2) . . ? C15 C14 C13 117.8(3) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C14 C15 C16 121.4(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C12 119.2(3) . . ? C16 C17 H17 120.4 . . ? C12 C17 H17 120.4 . . ? C8 N1 C11 124.1(2) . . ? C8 N1 H1 121(2) . . ? C11 N1 H1 115(2) . . ? C11 N2 C12 109.8(2) . . ? C1 O1 C7 121.5(2) . . ? C13 S1 C11 87.80(13) . . ? 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 O1 C1 C2 C3 178.3(2) . . . . ? C6 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C2 C3 C4 Cl1 179.5(2) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? Cl1 C4 C5 C6 -179.3(2) . . . . ? O1 C1 C6 C5 -178.0(2) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? O1 C7 C8 O2 -155.9(2) . . . . ? C9 C7 C8 O2 -29.5(4) . . . . ? C10 C7 C8 O2 91.6(3) . . . . ? O1 C7 C8 N1 28.6(3) . . . . ? C9 C7 C8 N1 155.0(2) . . . . ? C10 C7 C8 N1 -84.0(3) . . . . ? C17 C12 C13 C14 -1.0(4) . . . . ? N2 C12 C13 C14 179.1(2) . . . . ? C17 C12 C13 S1 178.5(2) . . . . ? N2 C12 C13 S1 -1.4(3) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? S1 C13 C14 C15 -179.2(2) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C14 C15 C16 C17 -1.2(4) . . . . ? C15 C16 C17 C12 0.3(4) . . . . ? N2 C12 C17 C16 -179.4(2) . . . . ? C13 C12 C17 C16 0.7(4) . . . . ? O2 C8 N1 C11 -6.5(4) . . . . ? C7 C8 N1 C11 169.1(2) . . . . ? N2 C11 N1 C8 -165.6(2) . . . . ? S1 C11 N1 C8 13.9(3) . . . . ? N1 C11 N2 C12 179.0(2) . . . . ? S1 C11 N2 C12 -0.5(3) . . . . ? C17 C12 N2 C11 -178.7(3) . . . . ? C13 C12 N2 C11 1.2(3) . . . . ? C2 C1 O1 C7 155.9(2) . . . . ? C6 C1 O1 C7 -25.8(4) . . . . ? C9 C7 O1 C1 -52.1(3) . . . . ? C10 C7 O1 C1 -171.9(2) . . . . ? C8 C7 O1 C1 73.5(3) . . . . ? C14 C13 S1 C11 -179.6(3) . . . . ? C12 C13 S1 C11 0.9(2) . . . . ? N2 C11 S1 C13 -0.2(2) . . . . ? N1 C11 S1 C13 -179.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.299 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.058 _iucr_refine_instructions_details ; TITL TIAZOL1 in Pbca CELL 0.71073 12.0968 10.0878 26.8071 90.000 90.000 90.000 ZERR 8.00 0.0027 0.0023 0.0060 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O S Cl UNIT 136 120 16 16 8 8 OMIT -3.00 50.00 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 CONF SIZE 0.21 0.25 0.27 DFIX 0.86 0.001 N1 H1 WGHT 0.009700 5.182700 FVAR 0.342880 TEMP -173 MOLE 1 C1 1 0.368910 0.817671 0.539474 11.000000 0.018710 0.017020 = 0.019600 0.002020 0.003810 -0.004050 C2 1 0.418942 0.707105 0.519294 11.000000 0.022970 0.016930 = 0.024640 0.002020 0.004220 -0.000750 AFIX 43 H2 2 0.477752 0.665318 0.536738 11.000000 -1.200000 AFIX 0 C3 1 0.384607 0.656607 0.474145 11.000000 0.035380 0.015580 = 0.025960 -0.001790 0.009500 -0.000580 AFIX 43 H3 2 0.419682 0.580796 0.460308 11.000000 -1.200000 AFIX 0 C4 1 0.298755 0.717405 0.449295 11.000000 0.028430 0.027630 = 0.019880 -0.002910 0.004210 -0.010730 C5 1 0.248489 0.828185 0.468750 11.000000 0.022560 0.035590 = 0.023170 0.002770 0.001900 0.000450 AFIX 43 H5 2 0.189929 0.869802 0.451077 11.000000 -1.200000 AFIX 0 C6 1 0.283244 0.879199 0.514166 11.000000 0.025890 0.024480 = 0.020630 -0.001410 0.005570 0.005630 AFIX 43 H6 2 0.248640 0.955596 0.527787 11.000000 -1.200000 AFIX 0 C7 1 0.399369 0.990237 0.602908 11.000000 0.021560 0.012160 = 0.024160 -0.001180 0.003160 -0.003040 C8 1 0.280035 1.020555 0.617992 11.000000 0.023940 0.013380 = 0.014110 -0.000120 -0.001760 -0.001660 C9 1 0.442483 1.091063 0.565713 11.000000 0.026780 0.018480 = 0.035410 0.003660 0.007900 -0.002110 AFIX 137 H9A 2 0.516915 1.065529 0.554942 11.000000 -1.500000 H9B 2 0.445179 1.178690 0.581449 11.000000 -1.500000 H9C 2 0.393213 1.094113 0.536716 11.000000 -1.500000 AFIX 0 C10 1 0.468165 0.992154 0.650232 11.000000 0.022300 0.025160 = 0.028680 -0.004870 -0.002370 -0.000050 AFIX 137 H10A 2 0.445936 0.918406 0.671810 11.000000 -1.500000 H10B 2 0.456438 1.076185 0.667796 11.000000 -1.500000 H10C 2 0.546555 0.983111 0.641654 11.000000 -1.500000 AFIX 0 C11 1 0.116870 0.926832 0.656815 11.000000 0.019330 0.014540 = 0.014800 -0.001130 -0.001080 0.000860 C12 1 -0.027917 0.865488 0.700292 11.000000 0.019940 0.017770 = 0.015200 -0.003470 -0.002930 -0.000740 C13 1 -0.060540 0.995854 0.689732 11.000000 0.022640 0.019930 = 0.014650 0.000790 -0.000030 -0.001300 C14 1 -0.160830 1.046070 0.706524 11.000000 0.029160 0.023900 = 0.023070 0.000440 0.006790 0.007360 AFIX 43 H14 2 -0.182624 1.134395 0.699147 11.000000 -1.200000 AFIX 0 C15 1 -0.227509 0.963580 0.734194 11.000000 0.023150 0.030710 = 0.022490 -0.005310 0.003520 0.003580 AFIX 43 H15 2 -0.296918 0.995319 0.745693 11.000000 -1.200000 AFIX 0 C16 1 -0.195353 0.834192 0.745741 11.000000 0.025290 0.024500 = 0.016570 -0.002960 0.002710 -0.006680 AFIX 43 H16 2 -0.242332 0.779820 0.765434 11.000000 -1.200000 AFIX 0 C17 1 -0.096033 0.784802 0.728794 11.000000 0.023020 0.019790 = 0.018040 -0.002290 0.000810 -0.002320 AFIX 43 H17 2 -0.074457 0.696615 0.736525 11.000000 -1.200000 AFIX 0 Cl1 6 0.255063 0.655667 0.391896 11.000000 0.049080 0.045100 = 0.023910 -0.010240 0.000320 -0.008850 N1 3 0.219319 0.915760 0.634209 11.000000 0.021200 0.011920 = 0.020080 0.000920 0.003170 0.001550 H1 2 0.244298 0.836101 0.632343 11.000000 -1.500000 N2 3 0.073850 0.828411 0.680390 11.000000 0.020800 0.014700 = 0.018020 -0.001190 0.000710 -0.001580 O1 4 0.409233 0.855305 0.585327 11.000000 0.023940 0.015170 = 0.019640 -0.000620 -0.000750 0.001490 O2 4 0.243367 1.133098 0.618465 11.000000 0.022440 0.013100 = 0.027410 0.002230 0.001380 -0.001840 S1 5 0.041352 1.075114 0.654930 11.000000 0.023900 0.014370 = 0.020800 0.001880 0.004770 0.003170 Q1 1 0.038200 1.151000 0.628200 11.000000 0.050000 0.30 Q2 1 0.280300 0.708100 0.422100 11.000000 0.050000 0.30 Q3 1 0.094300 0.998300 0.657900 11.000000 0.050000 0.29 Q4 1 -0.122600 1.008000 0.680300 11.000000 0.050000 0.28 Q5 1 -0.036600 1.047500 0.660900 11.000000 0.050000 0.28 HKLF 4 END ; # Attachment 'Compound 2.CIF' data_benzo2 _database_code_depnum_ccdc_archive 'CCDC 827869' #TrackingRef 'Compound 2.CIF' _audit_update_record ; 2011-10-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-methyl-1,3-benzothiazole-2-yl _chemical_melting_point 400 _chemical_formula_moiety 'C18 H17 Cl N2 O2 S' _chemical_formula_sum 'C18 H17 Cl N2 O2 S' _chemical_formula_weight 360.85 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' 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 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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.1449(13) _cell_length_b 9.9181(9) _cell_length_c 25.167(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3530.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3109 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9182 _exptl_absorpt_correction_T_max 0.9307 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23225 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3109 _reflns_number_gt 3035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0201P)^2^+6.9738P] 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 3109 _refine_ls_number_parameters 223 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.342 _refine_ls_restrained_S_all 1.342 _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 S1 S 0.08112(5) 0.43233(7) 0.15128(3) 0.01734(19) Uani 1 1 d . . . Cl1 Cl 0.07627(7) 0.27506(8) -0.18725(3) 0.0316(2) Uani 1 1 d . . . O1 O 0.32208(14) 0.2668(2) 0.00100(8) 0.0180(5) Uani 1 1 d . . . O2 O 0.22367(14) 0.5171(2) 0.08440(9) 0.0189(5) Uani 1 1 d . . . N2 N 0.08306(18) 0.1742(2) 0.12962(10) 0.0188(6) Uani 1 1 d . . . C1 C 0.2642(2) 0.2821(3) -0.04284(12) 0.0169(6) Uani 1 1 d . . . N1 N 0.20296(17) 0.2911(2) 0.08631(10) 0.0157(5) Uani 1 1 d D . . H1 H 0.227(2) 0.2131(15) 0.0797(13) 0.024 Uiso 1 1 d D . . C7 C 0.3377(2) 0.3794(3) 0.03654(12) 0.0167(6) Uani 1 1 d . . . C8 C 0.2494(2) 0.4040(3) 0.07077(12) 0.0156(6) Uani 1 1 d . . . C13 C -0.0022(2) 0.3291(3) 0.18284(12) 0.0178(7) Uani 1 1 d . . . C5 C 0.2307(2) 0.1998(3) -0.13056(13) 0.0244(8) Uani 1 1 d . . . H5 H 0.2460 0.1436 -0.1599 0.029 Uiso 1 1 calc R . . C11 C 0.1249(2) 0.2872(3) 0.11951(12) 0.0162(6) Uani 1 1 d . . . C16 C -0.1169(2) 0.1301(3) 0.22281(13) 0.0257(7) Uani 1 1 d . . . H16 H -0.1572 0.0618 0.2365 0.031 Uiso 1 1 calc R . . C4 C 0.1504(2) 0.2791(3) -0.13161(13) 0.0224(7) Uani 1 1 d . . . C3 C 0.1269(2) 0.3608(3) -0.08935(13) 0.0208(7) Uani 1 1 d . . . H3 H 0.0722 0.4164 -0.0910 0.025 Uiso 1 1 calc R . . C12 C 0.0095(2) 0.1956(3) 0.16572(12) 0.0180(7) Uani 1 1 d . . . C14 C -0.0700(2) 0.3635(3) 0.22038(12) 0.0209(7) Uani 1 1 d . . . H14 H -0.0769 0.4543 0.2317 0.025 Uiso 1 1 calc R . . C6 C 0.2883(2) 0.2033(3) -0.08634(13) 0.0214(7) Uani 1 1 d . . . H6 H 0.3449 0.1516 -0.0857 0.026 Uiso 1 1 calc R . . C9 C 0.3672(2) 0.5047(3) 0.00621(13) 0.0190(7) Uani 1 1 d . . . H9A H 0.4177 0.4816 -0.0189 0.028 Uiso 1 1 calc R . . H9B H 0.3903 0.5729 0.0312 0.028 Uiso 1 1 calc R . . H9C H 0.3128 0.5406 -0.0133 0.028 Uiso 1 1 calc R . . C2 C 0.1836(2) 0.3614(3) -0.04449(13) 0.0194(7) Uani 1 1 d . . . H2 H 0.1673 0.4162 -0.0149 0.023 Uiso 1 1 calc R . . C15 C -0.1275(2) 0.2631(3) 0.24105(13) 0.0233(7) Uani 1 1 d . . . C18 C -0.2012(2) 0.2949(4) 0.28288(14) 0.0333(9) Uani 1 1 d . . . H18A H -0.1901 0.3855 0.2971 0.050 Uiso 1 1 calc R . . H18B H -0.1970 0.2289 0.3117 0.050 Uiso 1 1 calc R . . H18C H -0.2644 0.2910 0.2669 0.050 Uiso 1 1 calc R . . C17 C -0.0497(2) 0.0958(3) 0.18568(13) 0.0234(7) Uani 1 1 d . . . H17 H -0.0438 0.0052 0.1739 0.028 Uiso 1 1 calc R . . C10 C 0.4163(2) 0.3310(3) 0.07343(13) 0.0217(7) Uani 1 1 d . . . H10A H 0.3976 0.2455 0.0899 0.033 Uiso 1 1 calc R . . H10B H 0.4273 0.3986 0.1011 0.033 Uiso 1 1 calc R . . H10C H 0.4744 0.3177 0.0529 0.033 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 S1 0.0181(4) 0.0124(4) 0.0215(4) -0.0016(3) 0.0010(3) 0.0012(3) Cl1 0.0466(5) 0.0231(4) 0.0253(5) 0.0010(4) -0.0135(4) -0.0060(4) O1 0.0200(10) 0.0121(10) 0.0219(11) -0.0004(9) -0.0001(9) 0.0039(9) O2 0.0185(11) 0.0113(11) 0.0268(12) 0.0002(9) 0.0012(9) 0.0009(8) N2 0.0220(13) 0.0135(13) 0.0210(14) 0.0008(11) 0.0032(11) -0.0017(11) C1 0.0190(15) 0.0129(15) 0.0188(16) 0.0033(13) 0.0007(12) -0.0030(12) N1 0.0173(13) 0.0096(12) 0.0203(14) 0.0006(11) 0.0021(10) 0.0006(10) C7 0.0155(14) 0.0128(14) 0.0217(16) 0.0011(13) -0.0014(12) -0.0008(12) C8 0.0149(14) 0.0140(16) 0.0180(15) 0.0018(12) -0.0072(12) 0.0009(12) C13 0.0165(15) 0.0194(16) 0.0175(16) 0.0017(13) -0.0019(12) 0.0007(13) C5 0.038(2) 0.0198(17) 0.0155(17) -0.0031(14) 0.0051(14) -0.0044(15) C11 0.0192(15) 0.0114(14) 0.0179(16) -0.0001(12) -0.0022(12) 0.0016(12) C16 0.0247(17) 0.0260(18) 0.0265(18) 0.0111(15) 0.0013(14) -0.0024(14) C4 0.0307(17) 0.0182(16) 0.0184(17) 0.0042(13) -0.0029(13) -0.0078(14) C3 0.0202(15) 0.0164(16) 0.0259(18) 0.0031(14) -0.0001(13) -0.0032(13) C12 0.0213(15) 0.0178(15) 0.0148(16) 0.0028(13) 0.0002(12) 0.0039(13) C14 0.0218(16) 0.0222(16) 0.0186(16) -0.0019(13) -0.0030(13) 0.0057(13) C6 0.0244(16) 0.0146(15) 0.0252(18) 0.0042(14) 0.0083(13) 0.0043(13) C9 0.0166(14) 0.0172(15) 0.0231(17) 0.0012(13) 0.0018(13) 0.0002(13) C2 0.0214(16) 0.0149(15) 0.0220(17) -0.0011(13) -0.0001(13) -0.0013(13) C15 0.0216(16) 0.0313(18) 0.0170(17) 0.0051(14) -0.0010(13) 0.0035(14) C18 0.0294(19) 0.043(2) 0.028(2) 0.0014(17) 0.0080(15) 0.0048(17) C17 0.0249(17) 0.0167(16) 0.0285(18) 0.0036(14) 0.0051(14) 0.0027(13) C10 0.0196(15) 0.0192(16) 0.0262(18) 0.0026(14) -0.0025(14) 0.0003(13) _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 S1 C13 1.751(3) . ? S1 C11 1.759(3) . ? Cl1 C4 1.750(3) . ? O1 C1 1.383(4) . ? O1 C7 1.448(4) . ? O2 C8 1.229(4) . ? N2 C11 1.293(4) . ? N2 C12 1.398(4) . ? C1 C2 1.386(4) . ? C1 C6 1.388(4) . ? N1 C8 1.356(4) . ? N1 C11 1.385(4) . ? N1 H1 0.8600(10) . ? C7 C9 1.517(4) . ? C7 C10 1.526(4) . ? C7 C8 1.537(4) . ? C13 C14 1.389(4) . ? C13 C12 1.402(4) . ? C5 C6 1.380(5) . ? C5 C4 1.382(5) . ? C5 H5 0.9500 . ? C16 C17 1.375(5) . ? C16 C15 1.405(5) . ? C16 H16 0.9500 . ? C4 C3 1.378(4) . ? C3 C2 1.385(4) . ? C3 H3 0.9500 . ? C12 C17 1.390(4) . ? C14 C15 1.388(5) . ? C14 H14 0.9500 . ? C6 H6 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C2 H2 0.9500 . ? C15 C18 1.515(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C17 H17 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C13 S1 C11 87.96(14) . . ? C1 O1 C7 119.9(2) . . ? C11 N2 C12 109.7(3) . . ? O1 C1 C2 125.0(3) . . ? O1 C1 C6 114.9(3) . . ? C2 C1 C6 119.9(3) . . ? C8 N1 C11 125.7(3) . . ? C8 N1 H1 120(2) . . ? C11 N1 H1 114(2) . . ? O1 C7 C9 111.3(2) . . ? O1 C7 C10 104.1(2) . . ? C9 C7 C10 111.3(2) . . ? O1 C7 C8 110.2(2) . . ? C9 C7 C8 112.1(2) . . ? C10 C7 C8 107.5(2) . . ? O2 C8 N1 122.0(3) . . ? O2 C8 C7 122.8(3) . . ? N1 C8 C7 115.1(2) . . ? C14 C13 C12 121.5(3) . . ? C14 C13 S1 129.0(2) . . ? C12 C13 S1 109.5(2) . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N2 C11 N1 120.5(3) . . ? N2 C11 S1 117.3(2) . . ? N1 C11 S1 122.2(2) . . ? C17 C16 C15 121.9(3) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C3 C4 C5 121.2(3) . . ? C3 C4 Cl1 119.1(3) . . ? C5 C4 Cl1 119.7(3) . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C17 C12 N2 125.1(3) . . ? C17 C12 C13 119.4(3) . . ? N2 C12 C13 115.5(3) . . ? C15 C14 C13 118.9(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C5 C6 C1 120.3(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C14 C15 C16 119.2(3) . . ? C14 C15 C18 121.0(3) . . ? C16 C15 C18 119.8(3) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C17 C12 119.0(3) . . ? C16 C17 H17 120.5 . . ? C12 C17 H17 120.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 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 C7 O1 C1 C2 -35.2(4) . . . . ? C7 O1 C1 C6 149.0(3) . . . . ? C1 O1 C7 C9 -50.9(3) . . . . ? C1 O1 C7 C10 -170.9(2) . . . . ? C1 O1 C7 C8 74.0(3) . . . . ? C11 N1 C8 O2 -1.8(5) . . . . ? C11 N1 C8 C7 176.3(3) . . . . ? O1 C7 C8 O2 -144.9(3) . . . . ? C9 C7 C8 O2 -20.4(4) . . . . ? C10 C7 C8 O2 102.3(3) . . . . ? O1 C7 C8 N1 37.0(3) . . . . ? C9 C7 C8 N1 161.5(3) . . . . ? C10 C7 C8 N1 -75.9(3) . . . . ? C11 S1 C13 C14 177.2(3) . . . . ? C11 S1 C13 C12 -1.2(2) . . . . ? C12 N2 C11 N1 177.4(3) . . . . ? C12 N2 C11 S1 -0.5(3) . . . . ? C8 N1 C11 N2 176.4(3) . . . . ? C8 N1 C11 S1 -5.8(4) . . . . ? C13 S1 C11 N2 1.0(3) . . . . ? C13 S1 C11 N1 -176.8(3) . . . . ? C6 C5 C4 C3 -0.2(5) . . . . ? C6 C5 C4 Cl1 -179.7(2) . . . . ? C5 C4 C3 C2 -1.5(5) . . . . ? Cl1 C4 C3 C2 178.0(2) . . . . ? C11 N2 C12 C17 -179.3(3) . . . . ? C11 N2 C12 C13 -0.5(4) . . . . ? C14 C13 C12 C17 1.7(5) . . . . ? S1 C13 C12 C17 -179.9(2) . . . . ? C14 C13 C12 N2 -177.2(3) . . . . ? S1 C13 C12 N2 1.3(3) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? S1 C13 C14 C15 -178.5(2) . . . . ? C4 C5 C6 C1 2.1(5) . . . . ? O1 C1 C6 C5 173.7(3) . . . . ? C2 C1 C6 C5 -2.4(5) . . . . ? C4 C3 C2 C1 1.2(4) . . . . ? O1 C1 C2 C3 -174.9(3) . . . . ? C6 C1 C2 C3 0.7(4) . . . . ? C13 C14 C15 C16 -1.1(5) . . . . ? C13 C14 C15 C18 178.8(3) . . . . ? C17 C16 C15 C14 1.2(5) . . . . ? C17 C16 C15 C18 -178.7(3) . . . . ? C15 C16 C17 C12 0.1(5) . . . . ? N2 C12 C17 C16 177.2(3) . . . . ? C13 C12 C17 C16 -1.5(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.422 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.065 _iucr_refine_instructions_details ; TITL BENZO2 in Pbca CELL 0.71073 14.1449 9.9181 25.1674 90.000 90.000 90.000 ZERR 8.00 0.0013 0.0009 0.0023 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O S Cl UNIT 144 136 16 16 8 8 OMIT -3.00 50.00 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 CONF DFIX 0.86 0.001 N1 H1 SIZE 0.21 0.23 0.25 WGHT 0.020000 6.978600 FVAR 0.259490 TEMP -173 MOLE 1 S1 5 0.081116 0.432334 0.151285 11.000000 0.018060 0.012410 = 0.021550 -0.001580 0.000980 0.001230 Cl1 6 0.076271 0.275056 -0.187252 11.000000 0.046570 0.023050 = 0.025260 0.000960 -0.013490 -0.005990 O1 4 0.322077 0.266797 0.001001 11.000000 0.020030 0.012050 = 0.021910 -0.000360 -0.000070 0.003930 O2 4 0.223671 0.517147 0.084401 11.000000 0.018490 0.011280 = 0.026840 0.000160 0.001170 0.000950 N2 3 0.083065 0.174209 0.129623 11.000000 0.021970 0.013540 = 0.020950 0.000840 0.003250 -0.001680 C1 1 0.264156 0.282080 -0.042838 11.000000 0.018950 0.012910 = 0.018830 0.003290 0.000700 -0.002970 N1 3 0.202964 0.291065 0.086311 11.000000 0.017250 0.009590 = 0.020280 0.000600 0.002120 0.000560 H1 2 0.226817 0.213101 0.079690 11.000000 -1.500000 C7 1 0.337717 0.379386 0.036544 11.000000 0.015480 0.012840 = 0.021730 0.001150 -0.001380 -0.000780 C8 1 0.249407 0.403989 0.070765 11.000000 0.014860 0.013990 = 0.018020 0.001790 -0.007190 0.000920 C13 1 -0.002164 0.329057 0.182839 11.000000 0.016510 0.019390 = 0.017500 0.001710 -0.001870 0.000720 C5 1 0.230671 0.199802 -0.130561 11.000000 0.037870 0.019780 = 0.015530 -0.003100 0.005150 -0.004370 AFIX 43 H5 2 0.245996 0.143621 -0.159895 11.000000 -1.200000 AFIX 0 C11 1 0.124904 0.287203 0.119510 11.000000 0.019240 0.011410 = 0.017950 -0.000130 -0.002190 0.001640 C16 1 -0.116852 0.130067 0.222807 11.000000 0.024720 0.026010 = 0.026450 0.011140 0.001280 -0.002400 AFIX 43 H16 2 -0.157203 0.061846 0.236508 11.000000 -1.200000 AFIX 0 C4 1 0.150361 0.279057 -0.131611 11.000000 0.030720 0.018160 = 0.018440 0.004190 -0.002920 -0.007830 C3 1 0.126868 0.360839 -0.089354 11.000000 0.020220 0.016350 = 0.025910 0.003100 -0.000140 -0.003170 AFIX 43 H3 2 0.072213 0.416352 -0.090983 11.000000 -1.200000 AFIX 0 C12 1 0.009469 0.195610 0.165722 11.000000 0.021340 0.017830 = 0.014750 0.002850 0.000180 0.003890 C14 1 -0.069988 0.363508 0.220382 11.000000 0.021830 0.022180 = 0.018570 -0.001890 -0.003050 0.005720 AFIX 43 H14 2 -0.076862 0.454341 0.231721 11.000000 -1.200000 AFIX 0 C6 1 0.288346 0.203305 -0.086343 11.000000 0.024360 0.014620 = 0.025200 0.004180 0.008260 0.004320 AFIX 43 H6 2 0.344854 0.151563 -0.085684 11.000000 -1.200000 AFIX 0 C9 1 0.367243 0.504720 0.006206 11.000000 0.016640 0.017200 = 0.023070 0.001190 0.001780 0.000200 AFIX 137 H9A 2 0.417654 0.481629 -0.018908 11.000000 -1.500000 H9B 2 0.390328 0.572877 0.031236 11.000000 -1.500000 H9C 2 0.312815 0.540600 -0.013302 11.000000 -1.500000 AFIX 0 C2 1 0.183577 0.361444 -0.044494 11.000000 0.021410 0.014890 = 0.022030 -0.001100 -0.000060 -0.001330 AFIX 43 H2 2 0.167263 0.416177 -0.014905 11.000000 -1.200000 AFIX 0 C15 1 -0.127531 0.263054 0.241047 11.000000 0.021580 0.031270 = 0.016980 0.005060 -0.001040 0.003500 C18 1 -0.201243 0.294924 0.282878 11.000000 0.029420 0.042920 = 0.027550 0.001370 0.008040 0.004790 AFIX 137 H18A 2 -0.190052 0.385549 0.297063 11.000000 -1.500000 H18B 2 -0.196997 0.228862 0.311737 11.000000 -1.500000 H18C 2 -0.264358 0.290975 0.266894 11.000000 -1.500000 AFIX 0 C17 1 -0.049665 0.095770 0.185683 11.000000 0.024940 0.016730 = 0.028490 0.003650 0.005080 0.002710 AFIX 43 H17 2 -0.043757 0.005197 0.173859 11.000000 -1.200000 AFIX 0 C10 1 0.416284 0.330965 0.073426 11.000000 0.019640 0.019190 = 0.026200 0.002570 -0.002460 0.000260 AFIX 137 H10A 2 0.397581 0.245529 0.089924 11.000000 -1.500000 H10B 2 0.427307 0.398596 0.101130 11.000000 -1.500000 H10C 2 0.474435 0.317663 0.052917 11.000000 -1.500000 AFIX 0 Q1 1 0.138700 0.255600 -0.195400 11.000000 0.050000 0.42 Q2 1 0.019800 0.395600 0.158500 11.000000 0.050000 0.41 Q3 1 0.119800 0.290800 -0.156700 11.000000 0.050000 0.33 Q4 1 0.115400 0.381800 0.123900 11.000000 0.050000 0.31 Q5 1 0.121400 0.348700 0.138000 11.000000 0.050000 0.30 HKLF 4 END ; # Attachment 'Compound 3.CIF' data_7hugo1m _database_code_depnum_ccdc_archive 'CCDC 827870' #TrackingRef 'Compound 3.CIF' _audit_update_record ; 2011-10-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-methoxy-1,3-benzothiazole-2-yl _chemical_melting_point 367 _chemical_formula_moiety 'C18 H17 Cl N2 O3 S, C H4 O' _chemical_formula_sum 'C19 H21 Cl N2 O4 S' _chemical_formula_weight 408.89 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' 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 _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 14.9642(18) _cell_length_b 7.7170(9) _cell_length_c 18.704(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.669(2) _cell_angle_gamma 90.00 _cell_volume 1930.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6878 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.334 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9212 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17913 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3394 _reflns_number_gt 2816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0507P)^2^+0.8395P] 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 3394 _refine_ls_number_parameters 254 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.74992(15) 0.1540(3) 0.45058(12) 0.0275(5) Uani 1 1 d . . . C2 C 0.79691(17) 0.2659(3) 0.42068(13) 0.0350(5) Uani 1 1 d . . . H2 H 0.7586 0.3289 0.3730 0.042 Uiso 1 1 calc R . . C3 C 0.89906(17) 0.2863(3) 0.45986(13) 0.0378(6) Uani 1 1 d . . . H3 H 0.9316 0.3624 0.4391 0.045 Uiso 1 1 calc R . . C4 C 0.95382(16) 0.1955(3) 0.52955(13) 0.0325(5) Uani 1 1 d . . . C5 C 0.90802(17) 0.0850(3) 0.56012(13) 0.0374(5) Uani 1 1 d . . . H5 H 0.9464 0.0232 0.6082 0.045 Uiso 1 1 calc R . . C6 C 0.80543(16) 0.0642(3) 0.52028(13) 0.0358(5) Uani 1 1 d . . . H6 H 0.7731 -0.0122 0.5411 0.043 Uiso 1 1 calc R . . C7 C 0.59672(15) 0.0171(3) 0.35298(12) 0.0311(5) Uani 1 1 d . . . C8 C 0.48503(15) 0.0520(3) 0.32561(12) 0.0302(5) Uani 1 1 d . . . C9 C 0.61992(17) 0.0408(3) 0.28219(13) 0.0387(6) Uani 1 1 d . . . H9A H 0.6089 0.1620 0.2647 0.058 Uiso 1 1 calc R . . H9B H 0.5760 -0.0341 0.2381 0.058 Uiso 1 1 calc R . . H9C H 0.6898 0.0097 0.2982 0.058 Uiso 1 1 calc R . . C10 C 0.62075(18) -0.1656(3) 0.38667(15) 0.0426(6) Uani 1 1 d . . . H10A H 0.6918 -0.1896 0.4042 0.064 Uiso 1 1 calc R . . H10B H 0.5803 -0.2489 0.3452 0.064 Uiso 1 1 calc R . . H10C H 0.6056 -0.1761 0.4323 0.064 Uiso 1 1 calc R . . C11 C 0.36485(15) 0.2049(3) 0.35587(12) 0.0260(5) Uani 1 1 d . . . C12 C 0.24623(15) 0.3187(3) 0.37937(12) 0.0266(5) Uani 1 1 d . . . C13 C 0.18557(15) 0.2203(2) 0.31262(12) 0.0249(4) Uani 1 1 d . . . C14 C 0.08161(15) 0.2144(3) 0.28316(12) 0.0265(4) Uani 1 1 d . . . H14 H 0.0408 0.1480 0.2372 0.032 Uiso 1 1 calc R . . C15 C 0.04086(15) 0.3099(3) 0.32397(12) 0.0273(5) Uani 1 1 d . . . C16 C 0.10105(16) 0.4092(3) 0.39098(12) 0.0300(5) Uani 1 1 d . . . H16 H 0.0708 0.4737 0.4176 0.036 Uiso 1 1 calc R . . C17 C 0.20272(16) 0.4153(3) 0.41897(12) 0.0304(5) Uani 1 1 d . . . H17 H 0.2429 0.4836 0.4644 0.036 Uiso 1 1 calc R . . C18 C -0.12468(16) 0.2034(3) 0.24327(14) 0.0382(6) Uani 1 1 d . . . H18A H -0.1250 0.2322 0.1921 0.057 Uiso 1 1 calc R . . H18B H -0.1925 0.2150 0.2382 0.057 Uiso 1 1 calc R . . H18C H -0.1015 0.0840 0.2580 0.057 Uiso 1 1 calc R . . C19 C 0.3902(2) 0.7385(4) 0.42743(16) 0.0529(7) Uani 1 1 d . . . H19A H 0.4192 0.8534 0.4462 0.079 Uiso 1 1 calc R . . H19B H 0.3171 0.7472 0.4012 0.079 Uiso 1 1 calc R . . H19C H 0.4129 0.6942 0.3892 0.079 Uiso 1 1 calc R . . Cl1 Cl 1.08273(4) 0.22732(9) 0.58200(4) 0.0495(2) Uani 1 1 d . . . H1 H 0.5063(16) 0.231(3) 0.4058(13) 0.074 Uiso 1 1 d D . . H6A H 0.421(2) 0.5224(13) 0.4783(18) 0.074 Uiso 1 1 d D . . N1 N 0.46134(13) 0.1712(2) 0.36782(10) 0.0285(4) Uani 1 1 d D . . N2 N 0.34823(12) 0.3089(2) 0.40266(10) 0.0287(4) Uani 1 1 d . . . O1 O 0.64678(10) 0.1445(2) 0.41465(9) 0.0339(4) Uani 1 1 d . . . O2 O 0.42170(11) -0.0273(2) 0.26943(9) 0.0403(4) Uani 1 1 d . . . O3 O -0.05944(10) 0.31818(19) 0.30347(9) 0.0334(4) Uani 1 1 d . . . O4 O 0.42065(12) 0.6258(2) 0.49245(10) 0.0429(4) Uani 1 1 d D . . S1 S 0.25998(4) 0.10987(7) 0.27776(3) 0.02756(16) 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 C1 0.0261(11) 0.0287(11) 0.0288(11) -0.0040(9) 0.0133(9) 0.0022(9) C2 0.0400(13) 0.0348(12) 0.0274(11) 0.0028(10) 0.0127(10) -0.0028(10) C3 0.0424(14) 0.0436(14) 0.0329(12) -0.0035(10) 0.0217(11) -0.0130(11) C4 0.0278(11) 0.0345(12) 0.0367(12) -0.0112(10) 0.0158(10) -0.0022(9) C5 0.0373(13) 0.0333(13) 0.0337(12) 0.0056(10) 0.0088(10) 0.0014(10) C6 0.0374(13) 0.0342(12) 0.0366(12) 0.0046(10) 0.0173(10) -0.0061(10) C7 0.0291(11) 0.0304(12) 0.0321(12) -0.0057(9) 0.0121(9) -0.0003(9) C8 0.0303(12) 0.0285(11) 0.0302(11) 0.0013(9) 0.0122(10) 0.0019(9) C9 0.0373(13) 0.0413(14) 0.0392(13) -0.0064(11) 0.0186(11) 0.0020(10) C10 0.0349(13) 0.0357(13) 0.0491(15) 0.0019(11) 0.0116(11) 0.0045(10) C11 0.0254(11) 0.0228(10) 0.0269(11) 0.0027(9) 0.0090(9) 0.0000(8) C12 0.0275(11) 0.0236(10) 0.0293(11) 0.0001(9) 0.0133(9) -0.0033(9) C13 0.0291(11) 0.0207(10) 0.0267(11) 0.0019(8) 0.0141(9) -0.0005(8) C14 0.0282(11) 0.0237(11) 0.0268(11) -0.0017(8) 0.0116(9) -0.0033(9) C15 0.0287(11) 0.0241(11) 0.0319(11) 0.0040(9) 0.0160(9) -0.0003(9) C16 0.0362(12) 0.0269(11) 0.0331(12) -0.0047(9) 0.0211(10) -0.0034(9) C17 0.0348(12) 0.0286(11) 0.0282(11) -0.0056(9) 0.0145(9) -0.0047(9) C18 0.0256(12) 0.0388(13) 0.0461(14) -0.0072(11) 0.0125(11) -0.0004(10) C19 0.0573(17) 0.0550(17) 0.0451(15) 0.0003(13) 0.0219(13) -0.0072(14) Cl1 0.0278(3) 0.0634(4) 0.0539(4) -0.0183(3) 0.0152(3) -0.0063(3) N1 0.0250(9) 0.0280(10) 0.0300(10) -0.0021(8) 0.0102(8) -0.0003(7) N2 0.0274(9) 0.0287(9) 0.0281(9) -0.0032(8) 0.0106(8) -0.0020(7) O1 0.0257(8) 0.0386(9) 0.0372(8) -0.0110(7) 0.0137(7) 0.0006(6) O2 0.0310(8) 0.0440(10) 0.0388(9) -0.0128(8) 0.0093(7) 0.0000(7) O3 0.0279(8) 0.0340(8) 0.0417(9) -0.0069(7) 0.0187(7) -0.0036(6) O4 0.0407(9) 0.0347(9) 0.0379(9) -0.0078(8) 0.0040(7) 0.0021(8) S1 0.0246(3) 0.0278(3) 0.0283(3) -0.0047(2) 0.0102(2) -0.0002(2) _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 1.377(3) . ? C1 C2 1.381(3) . ? C1 O1 1.381(2) . ? C2 C3 1.376(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.370(3) . ? C4 Cl1 1.745(2) . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.443(2) . ? C7 C10 1.521(3) . ? C7 C9 1.523(3) . ? C7 C8 1.536(3) . ? C8 O2 1.218(2) . ? C8 N1 1.359(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N2 1.291(3) . ? C11 N1 1.383(3) . ? C11 S1 1.754(2) . ? C12 N2 1.389(3) . ? C12 C13 1.394(3) . ? C12 C17 1.400(3) . ? C13 C14 1.399(3) . ? C13 S1 1.744(2) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 O3 1.374(2) . ? C15 C16 1.398(3) . ? C16 C17 1.370(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 O3 1.421(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O4 1.395(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1 H1 0.8600(11) . ? O4 H6A 0.8400(10) . ? 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 119.8(2) . . ? C6 C1 O1 120.08(19) . . ? C2 C1 O1 119.81(19) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 121.0(2) . . ? C5 C4 Cl1 119.15(18) . . ? C3 C4 Cl1 119.84(17) . . ? C4 C5 C6 119.3(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 120.3(2) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O1 C7 C10 111.04(17) . . ? O1 C7 C9 111.99(18) . . ? C10 C7 C9 111.56(19) . . ? O1 C7 C8 104.12(16) . . ? C10 C7 C8 108.66(18) . . ? C9 C7 C8 109.14(17) . . ? O2 C8 N1 122.45(19) . . ? O2 C8 C7 120.56(19) . . ? N1 C8 C7 116.98(18) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 N1 120.80(18) . . ? N2 C11 S1 116.87(15) . . ? N1 C11 S1 122.33(15) . . ? N2 C12 C13 115.69(18) . . ? N2 C12 C17 124.73(18) . . ? C13 C12 C17 119.56(19) . . ? C12 C13 C14 122.17(18) . . ? C12 C13 S1 109.43(15) . . ? C14 C13 S1 128.38(16) . . ? C15 C14 C13 116.95(19) . . ? C15 C14 H14 121.5 . . ? C13 C14 H14 121.5 . . ? O3 C15 C14 124.58(19) . . ? O3 C15 C16 114.09(18) . . ? C14 C15 C16 121.33(19) . . ? C17 C16 C15 121.29(19) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C12 118.69(19) . . ? C16 C17 H17 120.7 . . ? C12 C17 H17 120.7 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C8 N1 C11 124.00(18) . . ? C8 N1 H1 122(2) . . ? C11 N1 H1 114(2) . . ? C11 N2 C12 109.89(17) . . ? C1 O1 C7 119.40(15) . . ? C15 O3 C18 117.92(16) . . ? C19 O4 H6A 111(2) . . ? C13 S1 C11 88.12(10) . . ? 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 0.8(3) . . . . ? O1 C1 C2 C3 174.79(19) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C2 C3 C4 Cl1 -177.29(17) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? Cl1 C4 C5 C6 177.64(18) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? O1 C1 C6 C5 -174.4(2) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? O1 C7 C8 O2 174.97(19) . . . . ? C10 C7 C8 O2 -66.6(3) . . . . ? C9 C7 C8 O2 55.2(3) . . . . ? O1 C7 C8 N1 -6.4(2) . . . . ? C10 C7 C8 N1 112.0(2) . . . . ? C9 C7 C8 N1 -126.1(2) . . . . ? N2 C12 C13 C14 178.69(18) . . . . ? C17 C12 C13 C14 0.2(3) . . . . ? N2 C12 C13 S1 0.2(2) . . . . ? C17 C12 C13 S1 -178.30(16) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? S1 C13 C14 C15 177.43(16) . . . . ? C13 C14 C15 O3 -179.71(18) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? O3 C15 C16 C17 -179.79(19) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C15 C16 C17 C12 -0.4(3) . . . . ? N2 C12 C17 C16 -177.97(19) . . . . ? C13 C12 C17 C16 0.4(3) . . . . ? O2 C8 N1 C11 5.2(3) . . . . ? C7 C8 N1 C11 -173.42(18) . . . . ? N2 C11 N1 C8 173.9(2) . . . . ? S1 C11 N1 C8 -5.9(3) . . . . ? N1 C11 N2 C12 -178.87(18) . . . . ? S1 C11 N2 C12 1.0(2) . . . . ? C13 C12 N2 C11 -0.7(2) . . . . ? C17 C12 N2 C11 177.7(2) . . . . ? C6 C1 O1 C7 -93.4(2) . . . . ? C2 C1 O1 C7 92.6(2) . . . . ? C10 C7 O1 C1 65.8(2) . . . . ? C9 C7 O1 C1 -59.6(2) . . . . ? C8 C7 O1 C1 -177.44(17) . . . . ? C14 C15 O3 C18 9.0(3) . . . . ? C16 C15 O3 C18 -171.48(18) . . . . ? C12 C13 S1 C11 0.28(15) . . . . ? C14 C13 S1 C11 -178.10(19) . . . . ? N2 C11 S1 C13 -0.77(17) . . . . ? N1 C11 S1 C13 179.09(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.371 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.060 _iucr_refine_instructions_details ; TITL 7hugo1m in P2(1)/c CELL 0.71073 14.9642 7.7170 18.7036 90.000 116.669 90.000 ZERR 4.00 0.0018 0.0009 0.0028 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S Cl UNIT 76 84 8 16 4 4 OMIT -3.00 50.00 L.S. 5 ACTA BOND $H FMAP 2 PLAN 5 CONF DFIX 0.86 0.001 N1 H1 DFIX 0.84 0.001 O4 H6A SIZE 0.18 0.24 0.25 WGHT 0.050700 0.805200 FVAR 0.462630 TEMP -100.5 MOLE 1 C1 1 0.749920 0.153956 0.450577 11.000000 0.026120 0.028740 = 0.028850 -0.004040 0.013300 0.002200 C2 1 0.796908 0.265882 0.420679 11.000000 0.039960 0.034750 = 0.027440 0.002830 0.012720 -0.002820 AFIX 43 H2 2 0.758628 0.328910 0.372954 11.000000 -1.200000 AFIX 0 C3 1 0.899059 0.286332 0.459858 11.000000 0.042440 0.043560 = 0.032850 -0.003470 0.021700 -0.013000 AFIX 43 H3 2 0.931614 0.362390 0.439093 11.000000 -1.200000 AFIX 0 C4 1 0.953820 0.195475 0.529546 11.000000 0.027830 0.034460 = 0.036690 -0.011200 0.015750 -0.002220 C5 1 0.908019 0.084951 0.560116 11.000000 0.037290 0.033340 = 0.033690 0.005560 0.008820 0.001400 AFIX 43 H5 2 0.946371 0.023162 0.608211 11.000000 -1.200000 AFIX 0 C6 1 0.805429 0.064219 0.520282 11.000000 0.037360 0.034250 = 0.036550 0.004590 0.017320 -0.006100 AFIX 43 H6 2 0.773077 -0.012232 0.541067 11.000000 -1.200000 AFIX 0 C7 1 0.596719 0.017149 0.352975 11.000000 0.029110 0.030350 = 0.032080 -0.005660 0.012110 -0.000270 C8 1 0.485032 0.052005 0.325611 11.000000 0.030260 0.028530 = 0.030230 0.001330 0.012210 0.001900 C9 1 0.619921 0.040770 0.282187 11.000000 0.037300 0.041340 = 0.039200 -0.006400 0.018610 0.002010 AFIX 137 H9A 2 0.608857 0.161986 0.264742 11.000000 -1.500000 H9B 2 0.576005 -0.034132 0.238053 11.000000 -1.500000 H9C 2 0.689830 0.009655 0.298214 11.000000 -1.500000 AFIX 0 C10 1 0.620747 -0.165623 0.386666 11.000000 0.034900 0.035680 = 0.049130 0.001920 0.011570 0.004460 AFIX 137 H10A 2 0.691841 -0.189629 0.404211 11.000000 -1.500000 H10B 2 0.580274 -0.248945 0.345183 11.000000 -1.500000 H10C 2 0.605613 -0.176087 0.432316 11.000000 -1.500000 AFIX 0 C11 1 0.364846 0.204872 0.355866 11.000000 0.025390 0.022800 = 0.026880 0.002690 0.009030 -0.000040 C12 1 0.246230 0.318741 0.379366 11.000000 0.027470 0.023630 = 0.029260 0.000080 0.013340 -0.003300 C13 1 0.185567 0.220250 0.312618 11.000000 0.029130 0.020710 = 0.026680 0.001940 0.014090 -0.000530 C14 1 0.081611 0.214445 0.283160 11.000000 0.028220 0.023670 = 0.026780 -0.001720 0.011550 -0.003340 AFIX 43 H14 2 0.040839 0.148004 0.237235 11.000000 -1.200000 AFIX 0 C15 1 0.040862 0.309913 0.323970 11.000000 0.028660 0.024140 = 0.031890 0.004020 0.015980 -0.000260 C16 1 0.101046 0.409198 0.390979 11.000000 0.036160 0.026880 = 0.033100 -0.004700 0.021110 -0.003390 AFIX 43 H16 2 0.070823 0.473694 0.417607 11.000000 -1.200000 AFIX 0 C17 1 0.202724 0.415267 0.418968 11.000000 0.034840 0.028560 = 0.028170 -0.005640 0.014500 -0.004730 AFIX 43 H17 2 0.242931 0.483627 0.464358 11.000000 -1.200000 AFIX 0 C18 1 -0.124679 0.203447 0.243265 11.000000 0.025590 0.038810 = 0.046080 -0.007200 0.012490 -0.000420 AFIX 137 H18A 2 -0.125020 0.232222 0.192109 11.000000 -1.500000 H18B 2 -0.192498 0.215014 0.238185 11.000000 -1.500000 H18C 2 -0.101518 0.083961 0.257966 11.000000 -1.500000 AFIX 0 C19 1 0.390202 0.738537 0.427428 11.000000 0.057300 0.055030 = 0.045140 0.000320 0.021890 -0.007240 AFIX 137 H19A 2 0.419242 0.853379 0.446172 11.000000 -1.500000 H19B 2 0.317088 0.747226 0.401212 11.000000 -1.500000 H19C 2 0.412886 0.694216 0.389228 11.000000 -1.500000 AFIX 0 Cl1 6 1.082730 0.227322 0.582000 11.000000 0.027800 0.063350 = 0.053850 -0.018290 0.015170 -0.006300 H1 2 0.506291 0.230824 0.405764 11.000000 -1.500000 H6A 2 0.420607 0.522434 0.478326 11.000000 -1.500000 N1 3 0.461337 0.171170 0.367816 11.000000 0.025020 0.028030 = 0.029960 -0.002110 0.010180 -0.000310 N2 3 0.348230 0.308908 0.402658 11.000000 0.027350 0.028680 = 0.028070 -0.003190 0.010600 -0.001980 O1 4 0.646782 0.144464 0.414651 11.000000 0.025670 0.038620 = 0.037150 -0.010990 0.013740 0.000570 O2 4 0.421696 -0.027308 0.269425 11.000000 0.030980 0.044010 = 0.038800 -0.012770 0.009310 0.000010 O3 4 -0.059445 0.318176 0.303474 11.000000 0.027860 0.034040 = 0.041730 -0.006890 0.018700 -0.003590 O4 4 0.420653 0.625777 0.492447 11.000000 0.040740 0.034720 = 0.037920 -0.007770 0.003960 0.002100 S1 5 0.259981 0.109870 0.277756 11.000000 0.024590 0.027830 = 0.028340 -0.004690 0.010190 -0.000150 Q1 1 0.321300 0.151900 0.318200 11.000000 0.050000 0.37 Q2 1 0.622800 0.077900 0.380900 11.000000 0.050000 0.26 Q3 1 0.542600 0.037100 0.335900 11.000000 0.050000 0.26 Q4 1 0.774800 0.142800 0.491600 11.000000 0.050000 0.24 Q5 1 0.927700 0.215500 0.493300 11.000000 0.050000 0.24 HKLF 4 END ; # Attachment 'Compound 4.CIF' data_gabriel _database_code_depnum_ccdc_archive 'CCDC 827871' #TrackingRef 'Compound 4.CIF' _audit_update_record ; 2011-10-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-ethoxy-1,3-benzothiazole-2-yl _chemical_melting_point 425 _chemical_formula_moiety 'C19 H19 Cl N2 O3 S' _chemical_formula_sum 'C19 H19 Cl N2 O3 S' _chemical_formula_weight 390.87 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' 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 _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 23.731(2) _cell_length_b 13.7198(14) _cell_length_c 17.4841(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.160(2) _cell_angle_gamma 90.00 _cell_volume 5564.7(10) _cell_formula_units_Z 12 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9817 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9078 _exptl_absorpt_correction_T_max 0.9320 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 53185 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9817 _reflns_number_gt 8003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0222P)^2^+3.6629P] 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 9817 _refine_ls_number_parameters 721 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _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 0.30642(9) 0.53527(15) -0.13690(12) 0.0223(5) Uani 1 1 d . . . C2 C 0.36491(9) 0.55172(16) -0.11101(13) 0.0254(5) Uani 1 1 d . . . H2 H 0.3817 0.5490 -0.0567 0.030 Uiso 1 1 calc R . . C3 C 0.39883(9) 0.57209(16) -0.16415(13) 0.0247(5) Uani 1 1 d . . . H3 H 0.4390 0.5831 -0.1469 0.030 Uiso 1 1 calc R . . C4 C 0.37342(10) 0.57616(15) -0.24272(13) 0.0249(5) Uani 1 1 d . . . C5 C 0.31558(10) 0.55997(16) -0.26928(13) 0.0270(5) Uani 1 1 d . . . H5 H 0.2990 0.5629 -0.3237 0.032 Uiso 1 1 calc R . . C6 C 0.28161(10) 0.53929(15) -0.21582(13) 0.0251(5) Uani 1 1 d . . . H6 H 0.2415 0.5279 -0.2333 0.030 Uiso 1 1 calc R . . C7 C 0.26023(9) 0.42324(16) -0.06085(13) 0.0244(5) Uani 1 1 d . . . C8 C 0.23021(9) 0.43454(16) 0.00819(13) 0.0244(5) Uani 1 1 d . . . C9 C 0.31573(10) 0.36671(17) -0.03120(14) 0.0289(5) Uani 1 1 d . . . H9A H 0.3351 0.3551 -0.0746 0.043 Uiso 1 1 calc R . . H9B H 0.3067 0.3042 -0.0096 0.043 Uiso 1 1 calc R . . H9C H 0.3411 0.4045 0.0096 0.043 Uiso 1 1 calc R . . C10 C 0.22000(10) 0.37217(18) -0.12770(14) 0.0321(6) Uani 1 1 d . . . H10A H 0.1860 0.4130 -0.1463 0.048 Uiso 1 1 calc R . . H10B H 0.2080 0.3095 -0.1094 0.048 Uiso 1 1 calc R . . H10C H 0.2400 0.3610 -0.1705 0.048 Uiso 1 1 calc R . . C11 C 0.20888(9) 0.55168(16) 0.10266(12) 0.0227(5) Uani 1 1 d . . . C12 C 0.18582(9) 0.65015(15) 0.18963(13) 0.0232(5) Uani 1 1 d . . . C13 C 0.16047(9) 0.56554(15) 0.21074(12) 0.0225(5) Uani 1 1 d . . . C14 C 0.12826(9) 0.56426(16) 0.26893(13) 0.0253(5) Uani 1 1 d . . . H14 H 0.1113 0.5060 0.2828 0.030 Uiso 1 1 calc R . . C15 C 0.12227(9) 0.65223(16) 0.30547(13) 0.0251(5) Uani 1 1 d . . . C16 C 0.14886(9) 0.73695(16) 0.28636(13) 0.0274(5) Uani 1 1 d . . . H16 H 0.1450 0.7957 0.3135 0.033 Uiso 1 1 calc R . . C17 C 0.18034(9) 0.73669(16) 0.22911(13) 0.0271(5) Uani 1 1 d . . . H17 H 0.1982 0.7948 0.2165 0.033 Uiso 1 1 calc R . . C18 C 0.05515(10) 0.58534(17) 0.37514(13) 0.0282(5) Uani 1 1 d . . . H18A H 0.0795 0.5294 0.3974 0.034 Uiso 1 1 calc R . . H18B H 0.0298 0.5644 0.3254 0.034 Uiso 1 1 calc R . . C19 C 0.01936(10) 0.61911(18) 0.43166(14) 0.0330(6) Uani 1 1 d . . . H19A H 0.0448 0.6375 0.4813 0.049 Uiso 1 1 calc R . . H19B H -0.0062 0.5663 0.4408 0.049 Uiso 1 1 calc R . . H19C H -0.0038 0.6756 0.4097 0.049 Uiso 1 1 calc R . . C20 C 0.00631(9) 0.15356(15) 0.44458(13) 0.0238(5) Uani 1 1 d . . . C21 C 0.04220(9) 0.12153(16) 0.51308(13) 0.0256(5) Uani 1 1 d . . . H21 H 0.0826 0.1166 0.5164 0.031 Uiso 1 1 calc R . . C22 C 0.01891(10) 0.09688(16) 0.57654(13) 0.0263(5) Uani 1 1 d . . . H22 H 0.0431 0.0752 0.6239 0.032 Uiso 1 1 calc R . . C23 C -0.03989(10) 0.10412(15) 0.57038(13) 0.0267(5) Uani 1 1 d . . . C24 C -0.07571(10) 0.13808(16) 0.50313(14) 0.0272(5) Uani 1 1 d . . . H24 H -0.1159 0.1444 0.5004 0.033 Uiso 1 1 calc R . . C25 C -0.05246(9) 0.16283(16) 0.43978(13) 0.0264(5) Uani 1 1 d . . . H25 H -0.0767 0.1862 0.3930 0.032 Uiso 1 1 calc R . . C26 C 0.04794(10) 0.26549(16) 0.36264(13) 0.0253(5) Uani 1 1 d . . . C27 C 0.07869(10) 0.25190(16) 0.29451(13) 0.0274(5) Uani 1 1 d . . . C28 C 0.09140(10) 0.30499(17) 0.43187(13) 0.0286(5) Uani 1 1 d . . . H28A H 0.0719 0.3205 0.4745 0.043 Uiso 1 1 calc R . . H28B H 0.1092 0.3642 0.4162 0.043 Uiso 1 1 calc R . . H28C H 0.1213 0.2559 0.4497 0.043 Uiso 1 1 calc R . . C29 C -0.00313(10) 0.33286(17) 0.33736(14) 0.0324(6) Uani 1 1 d . . . H29A H -0.0320 0.3010 0.2967 0.049 Uiso 1 1 calc R . . H29B H 0.0097 0.3934 0.3166 0.049 Uiso 1 1 calc R . . H29C H -0.0201 0.3478 0.3824 0.049 Uiso 1 1 calc R . . C30 C 0.10877(9) 0.12770(17) 0.21157(13) 0.0260(5) Uani 1 1 d . . . C31 C 0.14039(9) 0.02317(16) 0.13552(12) 0.0249(5) Uani 1 1 d . . . C32 C 0.16765(9) 0.10638(16) 0.11494(13) 0.0258(5) Uani 1 1 d . . . C33 C 0.20236(9) 0.10447(17) 0.05964(13) 0.0274(5) Uani 1 1 d . . . H33 H 0.2215 0.1613 0.0472 0.033 Uiso 1 1 calc R . . C34 C 0.20764(10) 0.01613(17) 0.02383(13) 0.0280(5) Uani 1 1 d . . . C35 C 0.18046(10) -0.06798(17) 0.04327(14) 0.0296(5) Uani 1 1 d . . . H35 H 0.1852 -0.1279 0.0181 0.035 Uiso 1 1 calc R . . C36 C 0.14700(10) -0.06465(17) 0.09853(13) 0.0285(5) Uani 1 1 d . . . H36 H 0.1285 -0.1219 0.1114 0.034 Uiso 1 1 calc R . . C37 C 0.26143(11) 0.08664(18) -0.06273(15) 0.0367(6) Uani 1 1 d . . . H37A H 0.2911 0.1174 -0.0214 0.044 Uiso 1 1 calc R . . H37B H 0.2304 0.1347 -0.0812 0.044 Uiso 1 1 calc R . . C38 C 0.28780(12) 0.05360(19) -0.12984(16) 0.0408(6) Uani 1 1 d . . . H38A H 0.3186 0.0066 -0.1107 0.061 Uiso 1 1 calc R . . H38B H 0.3038 0.1100 -0.1524 0.061 Uiso 1 1 calc R . . H38C H 0.2581 0.0228 -0.1700 0.061 Uiso 1 1 calc R . . C39 C 0.61585(9) 0.16809(15) 0.17645(12) 0.0218(5) Uani 1 1 d . . . C40 C 0.67262(9) 0.19863(16) 0.18976(13) 0.0251(5) Uani 1 1 d . . . H40 H 0.6941 0.2063 0.2417 0.030 Uiso 1 1 calc R . . C41 C 0.69803(10) 0.21808(16) 0.12660(13) 0.0261(5) Uani 1 1 d . . . H41 H 0.7370 0.2390 0.1351 0.031 Uiso 1 1 calc R . . C42 C 0.66613(9) 0.20676(15) 0.05159(13) 0.0240(5) Uani 1 1 d . . . C43 C 0.60975(9) 0.17499(16) 0.03781(13) 0.0252(5) Uani 1 1 d . . . H43 H 0.5885 0.1663 -0.0142 0.030 Uiso 1 1 calc R . . C44 C 0.58454(9) 0.15595(15) 0.10088(13) 0.0231(5) Uani 1 1 d . . . H44 H 0.5456 0.1345 0.0922 0.028 Uiso 1 1 calc R . . C45 C 0.58947(9) 0.06472(15) 0.27714(12) 0.0220(5) Uani 1 1 d . . . C46 C 0.55453(9) 0.07915(16) 0.34024(12) 0.0226(5) Uani 1 1 d . . . C47 C 0.65044(9) 0.03741(17) 0.31724(13) 0.0279(5) Uani 1 1 d . . . H47A H 0.6736 0.0270 0.2778 0.042 Uiso 1 1 calc R . . H47B H 0.6497 -0.0226 0.3474 0.042 Uiso 1 1 calc R . . H47C H 0.6674 0.0902 0.3525 0.042 Uiso 1 1 calc R . . C48 C 0.56128(10) -0.01352(16) 0.22074(13) 0.0285(5) Uani 1 1 d . . . H48A H 0.5243 0.0105 0.1907 0.043 Uiso 1 1 calc R . . H48B H 0.5548 -0.0718 0.2501 0.043 Uiso 1 1 calc R . . H48C H 0.5865 -0.0299 0.1849 0.043 Uiso 1 1 calc R . . C49 C 0.50317(9) 0.20231(15) 0.39974(12) 0.0218(5) Uani 1 1 d . . . C50 C 0.46075(9) 0.30841(15) 0.46214(12) 0.0221(5) Uani 1 1 d . . . C51 C 0.45913(9) 0.22831(15) 0.51073(12) 0.0213(5) Uani 1 1 d . . . C52 C 0.43643(9) 0.23377(16) 0.57812(12) 0.0233(5) Uani 1 1 d . . . H52 H 0.4361 0.1788 0.6111 0.028 Uiso 1 1 calc R . . C53 C 0.41445(9) 0.32276(16) 0.59472(12) 0.0245(5) Uani 1 1 d . . . C54 C 0.41590(10) 0.40396(16) 0.54676(13) 0.0267(5) Uani 1 1 d . . . H54 H 0.4008 0.4644 0.5598 0.032 Uiso 1 1 calc R . . C55 C 0.43882(10) 0.39772(16) 0.48120(13) 0.0267(5) Uani 1 1 d . . . H55 H 0.4398 0.4533 0.4491 0.032 Uiso 1 1 calc R . . C56 C 0.38852(11) 0.26207(17) 0.71056(14) 0.0340(6) Uani 1 1 d . . . H56A H 0.4283 0.2408 0.7340 0.041 Uiso 1 1 calc R . . H56B H 0.3672 0.2059 0.6830 0.041 Uiso 1 1 calc R . . C57 C 0.35914(13) 0.29866(19) 0.77280(16) 0.0438(7) Uani 1 1 d . . . H57A H 0.3794 0.3564 0.7977 0.066 Uiso 1 1 calc R . . H57B H 0.3596 0.2477 0.8122 0.066 Uiso 1 1 calc R . . H57C H 0.3192 0.3159 0.7493 0.066 Uiso 1 1 calc R . . Cl1 Cl 0.41689(3) 0.60375(4) -0.30887(3) 0.03230(15) Uani 1 1 d . . . Cl2 Cl -0.06950(3) 0.06719(4) 0.64881(4) 0.03492(15) Uani 1 1 d . . . Cl3 Cl 0.69773(3) 0.23715(4) -0.02664(3) 0.03243(15) Uani 1 1 d . . . N1 N 0.23139(8) 0.52492(13) 0.03899(11) 0.0241(4) Uani 1 1 d D . . H1A H 0.2470(10) 0.5708(12) 0.0171(13) 0.036 Uiso 1 1 d D . . N2 N 0.21332(7) 0.64095(13) 0.12708(10) 0.0243(4) Uani 1 1 d . . . N3 N 0.07985(8) 0.15931(14) 0.26776(11) 0.0268(4) Uani 1 1 d D . . H3A H 0.0631(10) 0.1161(14) 0.2909(13) 0.040 Uiso 1 1 d D . . N4 N 0.10723(8) 0.03686(13) 0.19171(10) 0.0259(4) Uani 1 1 d . . . N5 N 0.53214(8) 0.16936(13) 0.34399(10) 0.0233(4) Uani 1 1 d D . . H5A H 0.5396(10) 0.2119(13) 0.3114(11) 0.035 Uiso 1 1 d D . . N6 N 0.48620(8) 0.29211(13) 0.39876(10) 0.0240(4) Uani 1 1 d . . . O1 O 0.27201(6) 0.52234(10) -0.08252(9) 0.0248(3) Uani 1 1 d . . . O2 O 0.20805(7) 0.36495(12) 0.03360(9) 0.0329(4) Uani 1 1 d . . . O3 O 0.09019(7) 0.66448(11) 0.36156(9) 0.0309(4) Uani 1 1 d . . . O4 O 0.02900(7) 0.16824(11) 0.37856(8) 0.0264(3) Uani 1 1 d . . . O5 O 0.10078(8) 0.32035(12) 0.26763(10) 0.0369(4) Uani 1 1 d . . . O6 O 0.23892(7) 0.00316(12) -0.03339(10) 0.0348(4) Uani 1 1 d . . . O7 O 0.58843(6) 0.15852(10) 0.23860(8) 0.0231(3) Uani 1 1 d . . . O8 O 0.54809(7) 0.01306(11) 0.38454(9) 0.0295(4) Uani 1 1 d . . . O9 O 0.38962(7) 0.33997(11) 0.65752(9) 0.0322(4) Uani 1 1 d . . . S1 S 0.17318(2) 0.46881(4) 0.15164(3) 0.02362(13) Uani 1 1 d . . . S2 S 0.14974(3) 0.20675(4) 0.16655(3) 0.02805(14) Uani 1 1 d . . . S3 S 0.49014(2) 0.12753(4) 0.47495(3) 0.02168(13) 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 C1 0.0254(11) 0.0185(11) 0.0243(12) -0.0020(9) 0.0085(9) 0.0018(9) C2 0.0268(12) 0.0266(12) 0.0218(12) -0.0004(9) 0.0029(9) -0.0011(9) C3 0.0219(11) 0.0234(12) 0.0286(13) -0.0008(9) 0.0052(9) 0.0008(9) C4 0.0328(13) 0.0184(11) 0.0266(12) -0.0004(9) 0.0131(10) 0.0020(9) C5 0.0340(13) 0.0234(12) 0.0223(12) -0.0017(9) 0.0035(10) 0.0021(10) C6 0.0233(11) 0.0221(12) 0.0280(12) -0.0005(9) 0.0016(9) 0.0017(9) C7 0.0240(12) 0.0229(12) 0.0278(12) -0.0022(9) 0.0089(9) -0.0037(9) C8 0.0199(11) 0.0265(12) 0.0261(12) -0.0017(10) 0.0036(9) -0.0014(9) C9 0.0290(13) 0.0275(12) 0.0319(13) 0.0005(10) 0.0103(10) 0.0027(10) C10 0.0323(13) 0.0351(14) 0.0292(13) -0.0070(11) 0.0074(10) -0.0074(11) C11 0.0197(11) 0.0242(12) 0.0236(12) -0.0026(9) 0.0033(9) -0.0006(9) C12 0.0188(11) 0.0249(12) 0.0247(12) -0.0018(9) 0.0015(9) 0.0013(9) C13 0.0194(11) 0.0222(11) 0.0246(12) -0.0015(9) 0.0013(9) 0.0020(9) C14 0.0249(12) 0.0225(12) 0.0285(12) 0.0003(9) 0.0056(10) -0.0004(9) C15 0.0226(11) 0.0276(12) 0.0254(12) -0.0021(10) 0.0060(9) 0.0020(9) C16 0.0257(12) 0.0232(12) 0.0340(13) -0.0061(10) 0.0079(10) 0.0006(9) C17 0.0234(12) 0.0248(12) 0.0325(13) -0.0008(10) 0.0043(10) -0.0020(9) C18 0.0306(12) 0.0255(12) 0.0302(13) -0.0007(10) 0.0104(10) 0.0003(10) C19 0.0352(14) 0.0332(14) 0.0323(14) -0.0038(11) 0.0112(11) -0.0050(11) C20 0.0307(12) 0.0165(11) 0.0253(12) -0.0050(9) 0.0081(10) 0.0000(9) C21 0.0239(11) 0.0232(12) 0.0292(12) -0.0016(10) 0.0042(10) 0.0043(9) C22 0.0300(12) 0.0234(12) 0.0245(12) -0.0020(9) 0.0034(10) 0.0035(10) C23 0.0353(13) 0.0168(11) 0.0300(13) -0.0057(9) 0.0119(10) -0.0008(9) C24 0.0238(12) 0.0217(12) 0.0358(14) -0.0044(10) 0.0058(10) 0.0002(9) C25 0.0262(12) 0.0229(12) 0.0271(12) -0.0031(9) -0.0015(10) -0.0007(9) C26 0.0284(12) 0.0195(11) 0.0278(12) -0.0005(9) 0.0055(10) 0.0001(9) C27 0.0309(13) 0.0241(12) 0.0251(12) 0.0015(10) 0.0015(10) 0.0007(10) C28 0.0286(12) 0.0275(13) 0.0290(13) -0.0034(10) 0.0044(10) 0.0004(10) C29 0.0315(13) 0.0265(13) 0.0374(14) 0.0031(11) 0.0030(11) 0.0006(10) C30 0.0272(12) 0.0285(13) 0.0211(12) 0.0020(9) 0.0024(9) -0.0015(10) C31 0.0261(12) 0.0262(12) 0.0210(11) 0.0036(9) 0.0019(9) 0.0001(9) C32 0.0285(12) 0.0256(12) 0.0217(12) 0.0030(9) 0.0016(9) 0.0022(10) C33 0.0275(12) 0.0283(13) 0.0260(12) 0.0069(10) 0.0045(10) -0.0008(10) C34 0.0265(12) 0.0338(13) 0.0235(12) 0.0019(10) 0.0049(10) 0.0042(10) C35 0.0307(13) 0.0252(12) 0.0331(13) 0.0004(10) 0.0074(10) 0.0020(10) C36 0.0305(13) 0.0256(12) 0.0295(13) 0.0014(10) 0.0064(10) -0.0025(10) C37 0.0360(14) 0.0336(14) 0.0447(15) 0.0044(12) 0.0182(12) 0.0017(11) C38 0.0442(16) 0.0384(15) 0.0456(16) 0.0040(12) 0.0228(13) -0.0021(12) C39 0.0279(12) 0.0173(11) 0.0224(11) 0.0005(9) 0.0104(9) 0.0010(9) C40 0.0277(12) 0.0242(12) 0.0229(12) 0.0015(9) 0.0044(9) -0.0002(9) C41 0.0235(12) 0.0276(12) 0.0281(12) 0.0013(10) 0.0074(10) -0.0019(9) C42 0.0296(12) 0.0202(11) 0.0252(12) 0.0022(9) 0.0124(10) 0.0032(9) C43 0.0291(12) 0.0230(12) 0.0231(12) 0.0006(9) 0.0044(10) 0.0033(9) C44 0.0212(11) 0.0195(11) 0.0286(12) 0.0019(9) 0.0050(9) 0.0007(9) C45 0.0272(12) 0.0174(11) 0.0232(11) 0.0016(9) 0.0089(9) 0.0005(9) C46 0.0237(11) 0.0220(12) 0.0221(11) -0.0008(9) 0.0047(9) -0.0003(9) C47 0.0282(12) 0.0294(13) 0.0273(12) 0.0015(10) 0.0084(10) 0.0033(10) C48 0.0361(13) 0.0242(12) 0.0263(12) 0.0003(10) 0.0094(10) -0.0016(10) C49 0.0245(11) 0.0218(12) 0.0200(11) 0.0014(9) 0.0071(9) 0.0010(9) C50 0.0234(11) 0.0238(12) 0.0200(11) -0.0003(9) 0.0063(9) 0.0004(9) C51 0.0201(11) 0.0209(11) 0.0227(11) -0.0022(9) 0.0041(9) -0.0014(9) C52 0.0268(12) 0.0209(11) 0.0233(11) 0.0013(9) 0.0079(9) -0.0036(9) C53 0.0255(12) 0.0284(12) 0.0212(11) -0.0025(9) 0.0086(9) -0.0003(9) C54 0.0336(13) 0.0232(12) 0.0246(12) -0.0004(9) 0.0089(10) 0.0066(10) C55 0.0338(13) 0.0232(12) 0.0240(12) 0.0045(9) 0.0080(10) 0.0040(10) C56 0.0480(15) 0.0288(13) 0.0301(13) 0.0013(10) 0.0195(12) 0.0000(11) C57 0.0656(19) 0.0314(14) 0.0435(16) 0.0036(12) 0.0320(14) 0.0057(13) Cl1 0.0434(3) 0.0270(3) 0.0320(3) -0.0004(2) 0.0205(3) -0.0008(3) Cl2 0.0460(4) 0.0263(3) 0.0383(3) -0.0003(3) 0.0223(3) 0.0028(3) Cl3 0.0386(3) 0.0350(3) 0.0280(3) 0.0048(2) 0.0169(3) 0.0004(3) N1 0.0250(10) 0.0238(10) 0.0249(10) -0.0021(8) 0.0080(8) -0.0048(8) N2 0.0232(10) 0.0251(10) 0.0250(10) -0.0021(8) 0.0056(8) -0.0020(8) N3 0.0322(11) 0.0249(11) 0.0241(10) 0.0002(8) 0.0082(8) -0.0029(8) N4 0.0302(10) 0.0247(11) 0.0226(10) 0.0006(8) 0.0053(8) -0.0007(8) N5 0.0299(10) 0.0211(10) 0.0220(10) 0.0032(8) 0.0124(8) 0.0020(8) N6 0.0286(10) 0.0234(10) 0.0219(10) 0.0009(8) 0.0093(8) 0.0033(8) O1 0.0262(8) 0.0220(8) 0.0288(8) -0.0019(6) 0.0117(7) -0.0011(6) O2 0.0392(10) 0.0275(9) 0.0374(10) -0.0040(7) 0.0205(8) -0.0066(7) O3 0.0346(9) 0.0244(9) 0.0377(10) -0.0071(7) 0.0165(8) -0.0023(7) O4 0.0358(9) 0.0207(8) 0.0240(8) -0.0027(6) 0.0090(7) -0.0011(7) O5 0.0507(11) 0.0253(9) 0.0384(10) 0.0013(8) 0.0174(8) -0.0041(8) O6 0.0422(10) 0.0284(9) 0.0380(10) -0.0001(7) 0.0183(8) -0.0001(8) O7 0.0296(8) 0.0192(8) 0.0238(8) 0.0017(6) 0.0134(7) 0.0015(6) O8 0.0408(10) 0.0221(8) 0.0302(9) 0.0043(7) 0.0176(7) 0.0027(7) O9 0.0471(10) 0.0242(9) 0.0309(9) 0.0000(7) 0.0210(8) 0.0052(7) S1 0.0244(3) 0.0220(3) 0.0257(3) -0.0029(2) 0.0081(2) -0.0012(2) S2 0.0361(3) 0.0227(3) 0.0262(3) 0.0022(2) 0.0087(2) -0.0012(2) S3 0.0265(3) 0.0188(3) 0.0218(3) 0.0004(2) 0.0099(2) 0.0003(2) _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 1.383(3) . ? C1 C2 1.385(3) . ? C1 O1 1.389(2) . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.371(3) . ? C4 Cl1 1.746(2) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.454(3) . ? C7 C10 1.516(3) . ? C7 C9 1.522(3) . ? C7 C8 1.533(3) . ? C8 O2 1.218(3) . ? C8 N1 1.350(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N2 1.294(3) . ? C11 N1 1.382(3) . ? C11 S1 1.746(2) . ? C12 N2 1.392(3) . ? C12 C13 1.393(3) . ? C12 C17 1.393(3) . ? C13 C14 1.395(3) . ? C13 S1 1.747(2) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 O3 1.372(3) . ? C15 C16 1.396(3) . ? C16 C17 1.369(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 O3 1.418(3) . ? C18 C19 1.505(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.385(3) . ? C20 C21 1.387(3) . ? C20 O4 1.387(3) . ? C21 C22 1.382(3) . ? C21 H21 0.9500 . ? C22 C23 1.380(3) . ? C22 H22 0.9500 . ? C23 C24 1.379(3) . ? C23 Cl2 1.743(2) . ? C24 C25 1.380(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 O4 1.453(3) . ? C26 C29 1.514(3) . ? C26 C28 1.516(3) . ? C26 C27 1.534(3) . ? C27 O5 1.217(3) . ? C27 N3 1.356(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 N4 1.292(3) . ? C30 N3 1.381(3) . ? C30 S2 1.750(2) . ? C31 C36 1.392(3) . ? C31 N4 1.395(3) . ? C31 C32 1.396(3) . ? C32 C33 1.396(3) . ? C32 S2 1.747(2) . ? C33 C34 1.382(3) . ? C33 H33 0.9500 . ? C34 O6 1.377(3) . ? C34 C35 1.398(3) . ? C35 C36 1.374(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 O6 1.406(3) . ? C37 C38 1.511(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C44 1.383(3) . ? C39 C40 1.383(3) . ? C39 O7 1.385(2) . ? C40 C41 1.391(3) . ? C40 H40 0.9500 . ? C41 C42 1.378(3) . ? C41 H41 0.9500 . ? C42 C43 1.379(3) . ? C42 Cl3 1.743(2) . ? C43 C44 1.386(3) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 O7 1.450(2) . ? C45 C48 1.515(3) . ? C45 C47 1.516(3) . ? C45 C46 1.526(3) . ? C46 O8 1.223(3) . ? C46 N5 1.354(3) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 N6 1.295(3) . ? C49 N5 1.382(3) . ? C49 S3 1.746(2) . ? C50 N6 1.387(3) . ? C50 C51 1.395(3) . ? C50 C55 1.399(3) . ? C51 C52 1.397(3) . ? C51 S3 1.743(2) . ? C52 C53 1.382(3) . ? C52 H52 0.9500 . ? C53 O9 1.372(3) . ? C53 C54 1.399(3) . ? C54 C55 1.371(3) . ? C54 H54 0.9500 . ? C55 H55 0.9500 . ? C56 O9 1.419(3) . ? C56 C57 1.497(3) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? N1 H1A 0.8600(10) . ? N3 H3A 0.8599(10) . ? N5 H5A 0.8600(10) . ? 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 120.4(2) . . ? C6 C1 O1 120.00(19) . . ? C2 C1 O1 119.37(19) . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.9(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 121.8(2) . . ? C5 C4 Cl1 119.98(17) . . ? C3 C4 Cl1 118.22(17) . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.7(2) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O1 C7 C10 110.83(18) . . ? O1 C7 C9 111.41(17) . . ? C10 C7 C9 112.72(19) . . ? O1 C7 C8 104.91(17) . . ? C10 C7 C8 109.40(17) . . ? C9 C7 C8 107.19(18) . . ? O2 C8 N1 123.3(2) . . ? O2 C8 C7 121.0(2) . . ? N1 C8 C7 115.66(19) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 N1 119.92(19) . . ? N2 C11 S1 117.94(16) . . ? N1 C11 S1 122.13(16) . . ? N2 C12 C13 115.64(19) . . ? N2 C12 C17 125.1(2) . . ? C13 C12 C17 119.2(2) . . ? C12 C13 C14 122.5(2) . . ? C12 C13 S1 109.78(16) . . ? C14 C13 S1 127.67(17) . . ? C15 C14 C13 116.7(2) . . ? C15 C14 H14 121.6 . . ? C13 C14 H14 121.6 . . ? O3 C15 C14 124.2(2) . . ? O3 C15 C16 114.56(19) . . ? C14 C15 C16 121.3(2) . . ? C17 C16 C15 121.1(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C12 119.1(2) . . ? C16 C17 H17 120.4 . . ? C12 C17 H17 120.4 . . ? O3 C18 C19 107.83(18) . . ? O3 C18 H18A 110.1 . . ? C19 C18 H18A 110.1 . . ? O3 C18 H18B 110.1 . . ? C19 C18 H18B 110.1 . . ? H18A C18 H18B 108.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 120.6(2) . . ? C25 C20 O4 119.9(2) . . ? C21 C20 O4 119.29(19) . . ? C22 C21 C20 119.6(2) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C23 C22 C21 119.2(2) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C24 C23 C22 121.5(2) . . ? C24 C23 Cl2 119.40(18) . . ? C22 C23 Cl2 119.09(18) . . ? C23 C24 C25 119.3(2) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C20 119.8(2) . . ? C24 C25 H25 120.1 . . ? C20 C25 H25 120.1 . . ? O4 C26 C29 110.83(18) . . ? O4 C26 C28 111.17(18) . . ? C29 C26 C28 112.52(19) . . ? O4 C26 C27 104.72(17) . . ? C29 C26 C27 109.27(18) . . ? C28 C26 C27 107.98(18) . . ? O5 C27 N3 123.2(2) . . ? O5 C27 C26 121.3(2) . . ? N3 C27 C26 115.42(19) . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N4 C30 N3 120.2(2) . . ? N4 C30 S2 117.62(17) . . ? N3 C30 S2 122.11(17) . . ? C36 C31 N4 125.4(2) . . ? C36 C31 C32 119.0(2) . . ? N4 C31 C32 115.6(2) . . ? C31 C32 C33 122.4(2) . . ? C31 C32 S2 109.59(16) . . ? C33 C32 S2 127.99(18) . . ? C34 C33 C32 116.9(2) . . ? C34 C33 H33 121.5 . . ? C32 C33 H33 121.5 . . ? O6 C34 C33 123.8(2) . . ? O6 C34 C35 114.6(2) . . ? C33 C34 C35 121.5(2) . . ? C36 C35 C34 120.5(2) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 119.6(2) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? O6 C37 C38 106.9(2) . . ? O6 C37 H37A 110.3 . . ? C38 C37 H37A 110.3 . . ? O6 C37 H37B 110.3 . . ? C38 C37 H37B 110.3 . . ? H37A C37 H37B 108.6 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C44 C39 C40 120.4(2) . . ? C44 C39 O7 119.45(19) . . ? C40 C39 O7 119.90(19) . . ? C39 C40 C41 119.6(2) . . ? C39 C40 H40 120.2 . . ? C41 C40 H40 120.2 . . ? C42 C41 C40 119.4(2) . . ? C42 C41 H41 120.3 . . ? C40 C41 H41 120.3 . . ? C41 C42 C43 121.3(2) . . ? C41 C42 Cl3 118.61(17) . . ? C43 C42 Cl3 120.02(17) . . ? C42 C43 C44 119.1(2) . . ? C42 C43 H43 120.5 . . ? C44 C43 H43 120.5 . . ? C39 C44 C43 120.2(2) . . ? C39 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? O7 C45 C48 111.38(17) . . ? O7 C45 C47 110.82(17) . . ? C48 C45 C47 111.94(18) . . ? O7 C45 C46 105.19(16) . . ? C48 C45 C46 109.26(17) . . ? C47 C45 C46 107.97(17) . . ? O8 C46 N5 123.0(2) . . ? O8 C46 C45 121.41(19) . . ? N5 C46 C45 115.60(18) . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? N6 C49 N5 120.09(19) . . ? N6 C49 S3 117.71(16) . . ? N5 C49 S3 122.17(16) . . ? N6 C50 C51 115.60(19) . . ? N6 C50 C55 125.32(19) . . ? C51 C50 C55 119.05(19) . . ? C50 C51 C52 122.46(19) . . ? C50 C51 S3 109.78(15) . . ? C52 C51 S3 127.74(17) . . ? C53 C52 C51 117.0(2) . . ? C53 C52 H52 121.5 . . ? C51 C52 H52 121.5 . . ? O9 C53 C52 124.4(2) . . ? O9 C53 C54 114.31(19) . . ? C52 C53 C54 121.3(2) . . ? C55 C54 C53 121.0(2) . . ? C55 C54 H54 119.5 . . ? C53 C54 H54 119.5 . . ? C54 C55 C50 119.1(2) . . ? C54 C55 H55 120.4 . . ? C50 C55 H55 120.4 . . ? O9 C56 C57 107.34(19) . . ? O9 C56 H56A 110.2 . . ? C57 C56 H56A 110.2 . . ? O9 C56 H56B 110.2 . . ? C57 C56 H56B 110.2 . . ? H56A C56 H56B 108.5 . . ? C56 C57 H57A 109.5 . . ? C56 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C56 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C8 N1 C11 125.91(19) . . ? C8 N1 H1A 118.0(17) . . ? C11 N1 H1A 116.0(17) . . ? C11 N2 C12 109.02(18) . . ? C27 N3 C30 126.06(19) . . ? C27 N3 H3A 116.0(18) . . ? C30 N3 H3A 117.8(18) . . ? C30 N4 C31 109.33(19) . . ? C46 N5 C49 126.29(18) . . ? C46 N5 H5A 116.8(17) . . ? C49 N5 H5A 116.6(17) . . ? C49 N6 C50 109.23(18) . . ? C1 O1 C7 118.08(15) . . ? C15 O3 C18 117.32(17) . . ? C20 O4 C26 118.85(16) . . ? C34 O6 C37 117.66(18) . . ? C39 O7 C45 118.92(15) . . ? C53 O9 C56 117.63(17) . . ? C11 S1 C13 87.57(10) . . ? C32 S2 C30 87.85(11) . . ? C51 S3 C49 87.67(10) . . ? 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 -0.1(3) . . . . ? O1 C1 C2 C3 -175.04(19) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C2 C3 C4 Cl1 179.10(17) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? Cl1 C4 C5 C6 -179.25(17) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? O1 C1 C6 C5 174.85(19) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? O1 C7 C8 O2 170.50(19) . . . . ? C10 C7 C8 O2 51.6(3) . . . . ? C9 C7 C8 O2 -71.0(3) . . . . ? O1 C7 C8 N1 -10.9(2) . . . . ? C10 C7 C8 N1 -129.9(2) . . . . ? C9 C7 C8 N1 107.6(2) . . . . ? N2 C12 C13 C14 -175.89(19) . . . . ? C17 C12 C13 C14 1.7(3) . . . . ? N2 C12 C13 S1 1.7(2) . . . . ? C17 C12 C13 S1 179.34(16) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? S1 C13 C14 C15 -177.05(17) . . . . ? C13 C14 C15 O3 177.32(19) . . . . ? C13 C14 C15 C16 -2.0(3) . . . . ? O3 C15 C16 C17 -177.3(2) . . . . ? C14 C15 C16 C17 2.0(3) . . . . ? C15 C16 C17 C12 -0.1(3) . . . . ? N2 C12 C17 C16 175.7(2) . . . . ? C13 C12 C17 C16 -1.7(3) . . . . ? C25 C20 C21 C22 1.3(3) . . . . ? O4 C20 C21 C22 -173.18(19) . . . . ? C20 C21 C22 C23 0.4(3) . . . . ? C21 C22 C23 C24 -1.9(3) . . . . ? C21 C22 C23 Cl2 176.81(17) . . . . ? C22 C23 C24 C25 1.8(3) . . . . ? Cl2 C23 C24 C25 -176.90(17) . . . . ? C23 C24 C25 C20 -0.2(3) . . . . ? C21 C20 C25 C24 -1.4(3) . . . . ? O4 C20 C25 C24 173.05(19) . . . . ? O4 C26 C27 O5 -178.7(2) . . . . ? C29 C26 C27 O5 62.5(3) . . . . ? C28 C26 C27 O5 -60.2(3) . . . . ? O4 C26 C27 N3 0.6(2) . . . . ? C29 C26 C27 N3 -118.2(2) . . . . ? C28 C26 C27 N3 119.1(2) . . . . ? C36 C31 C32 C33 -1.3(3) . . . . ? N4 C31 C32 C33 179.93(19) . . . . ? C36 C31 C32 S2 177.36(17) . . . . ? N4 C31 C32 S2 -1.4(2) . . . . ? C31 C32 C33 C34 1.7(3) . . . . ? S2 C32 C33 C34 -176.77(17) . . . . ? C32 C33 C34 O6 178.07(19) . . . . ? C32 C33 C34 C35 -1.3(3) . . . . ? O6 C34 C35 C36 -178.8(2) . . . . ? C33 C34 C35 C36 0.6(3) . . . . ? C34 C35 C36 C31 -0.2(3) . . . . ? N4 C31 C36 C35 179.2(2) . . . . ? C32 C31 C36 C35 0.6(3) . . . . ? C44 C39 C40 C41 0.6(3) . . . . ? O7 C39 C40 C41 -173.18(19) . . . . ? C39 C40 C41 C42 0.1(3) . . . . ? C40 C41 C42 C43 -1.1(3) . . . . ? C40 C41 C42 Cl3 176.95(17) . . . . ? C41 C42 C43 C44 1.2(3) . . . . ? Cl3 C42 C43 C44 -176.75(16) . . . . ? C40 C39 C44 C43 -0.5(3) . . . . ? O7 C39 C44 C43 173.38(18) . . . . ? C42 C43 C44 C39 -0.5(3) . . . . ? O7 C45 C46 O8 -178.64(19) . . . . ? C48 C45 C46 O8 61.7(3) . . . . ? C47 C45 C46 O8 -60.3(3) . . . . ? O7 C45 C46 N5 0.7(2) . . . . ? C48 C45 C46 N5 -119.0(2) . . . . ? C47 C45 C46 N5 119.0(2) . . . . ? N6 C50 C51 C52 178.11(19) . . . . ? C55 C50 C51 C52 -0.1(3) . . . . ? N6 C50 C51 S3 -0.7(2) . . . . ? C55 C50 C51 S3 -178.91(17) . . . . ? C50 C51 C52 C53 0.9(3) . . . . ? S3 C51 C52 C53 179.48(17) . . . . ? C51 C52 C53 O9 178.63(19) . . . . ? C51 C52 C53 C54 -1.1(3) . . . . ? O9 C53 C54 C55 -179.2(2) . . . . ? C52 C53 C54 C55 0.5(3) . . . . ? C53 C54 C55 C50 0.3(3) . . . . ? N6 C50 C55 C54 -178.5(2) . . . . ? C51 C50 C55 C54 -0.5(3) . . . . ? O2 C8 N1 C11 0.7(3) . . . . ? C7 C8 N1 C11 -177.86(19) . . . . ? N2 C11 N1 C8 179.3(2) . . . . ? S1 C11 N1 C8 -1.6(3) . . . . ? N1 C11 N2 C12 178.00(18) . . . . ? S1 C11 N2 C12 -1.2(2) . . . . ? C13 C12 N2 C11 -0.4(3) . . . . ? C17 C12 N2 C11 -177.9(2) . . . . ? O5 C27 N3 C30 4.8(4) . . . . ? C26 C27 N3 C30 -174.48(19) . . . . ? N4 C30 N3 C27 179.0(2) . . . . ? S2 C30 N3 C27 0.5(3) . . . . ? N3 C30 N4 C31 -178.87(19) . . . . ? S2 C30 N4 C31 -0.3(2) . . . . ? C36 C31 N4 C30 -177.5(2) . . . . ? C32 C31 N4 C30 1.1(3) . . . . ? O8 C46 N5 C49 4.9(3) . . . . ? C45 C46 N5 C49 -174.37(19) . . . . ? N6 C49 N5 C46 176.7(2) . . . . ? S3 C49 N5 C46 -1.2(3) . . . . ? N5 C49 N6 C50 -177.31(18) . . . . ? S3 C49 N6 C50 0.7(2) . . . . ? C51 C50 N6 C49 0.0(3) . . . . ? C55 C50 N6 C49 178.1(2) . . . . ? C6 C1 O1 C7 89.8(2) . . . . ? C2 C1 O1 C7 -95.3(2) . . . . ? C10 C7 O1 C1 -70.8(2) . . . . ? C9 C7 O1 C1 55.5(2) . . . . ? C8 C7 O1 C1 171.18(16) . . . . ? C14 C15 O3 C18 -8.7(3) . . . . ? C16 C15 O3 C18 170.68(19) . . . . ? C19 C18 O3 C15 -173.71(18) . . . . ? C25 C20 O4 C26 90.9(2) . . . . ? C21 C20 O4 C26 -94.6(2) . . . . ? C29 C26 O4 C20 -71.0(2) . . . . ? C28 C26 O4 C20 55.0(2) . . . . ? C27 C26 O4 C20 171.33(17) . . . . ? C33 C34 O6 C37 -7.1(3) . . . . ? C35 C34 O6 C37 172.3(2) . . . . ? C38 C37 O6 C34 -174.00(19) . . . . ? C44 C39 O7 C45 93.9(2) . . . . ? C40 C39 O7 C45 -92.2(2) . . . . ? C48 C45 O7 C39 -60.3(2) . . . . ? C47 C45 O7 C39 65.0(2) . . . . ? C46 C45 O7 C39 -178.55(16) . . . . ? C52 C53 O9 C56 2.6(3) . . . . ? C54 C53 O9 C56 -177.7(2) . . . . ? C57 C56 O9 C53 -179.6(2) . . . . ? N2 C11 S1 C13 1.84(18) . . . . ? N1 C11 S1 C13 -177.30(18) . . . . ? C12 C13 S1 C11 -1.86(16) . . . . ? C14 C13 S1 C11 175.6(2) . . . . ? C31 C32 S2 C30 0.93(16) . . . . ? C33 C32 S2 C30 179.5(2) . . . . ? N4 C30 S2 C32 -0.38(18) . . . . ? N3 C30 S2 C32 178.16(19) . . . . ? C50 C51 S3 C49 0.83(16) . . . . ? C52 C51 S3 C49 -177.9(2) . . . . ? N6 C49 S3 C51 -0.92(18) . . . . ? N5 C49 S3 C51 177.03(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.359 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.056 _iucr_refine_instructions_details ; TITL GABRIEL in P2(1)/c CELL 0.71073 23.7306 13.7198 17.4841 90.000 102.160 90.000 ZERR 12.00 0.0024 0.0014 0.0018 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S Cl UNIT 228 228 24 36 12 12 OMIT -3.00 50.00 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 DFIX 0.86 0.001 N3 H3A N1 H1A N5 H5A SIZE 0.21 0.25 0.29 CONF WGHT 0.022200 3.662900 FVAR 0.033240 TEMP -173 MOLE 2 C1 1 0.306424 0.535267 -0.136895 11.000000 0.025440 0.018490 = 0.024330 -0.002050 0.008490 0.001760 C2 1 0.364907 0.551718 -0.111013 11.000000 0.026790 0.026650 = 0.021830 -0.000380 0.002910 -0.001140 AFIX 43 H2 2 0.381673 0.548981 -0.056693 11.000000 -1.200000 AFIX 0 C3 1 0.398832 0.572092 -0.164149 11.000000 0.021910 0.023450 = 0.028590 -0.000840 0.005210 0.000760 AFIX 43 H3 2 0.439027 0.583139 -0.146926 11.000000 -1.200000 AFIX 0 C4 1 0.373417 0.576159 -0.242721 11.000000 0.032850 0.018360 = 0.026570 -0.000400 0.013130 0.001950 C5 1 0.315585 0.559972 -0.269285 11.000000 0.034050 0.023450 = 0.022330 -0.001680 0.003490 0.002060 AFIX 43 H5 2 0.299001 0.562895 -0.323654 11.000000 -1.200000 AFIX 0 C6 1 0.281613 0.539285 -0.215817 11.000000 0.023350 0.022120 = 0.028010 -0.000500 0.001590 0.001660 AFIX 43 H6 2 0.241473 0.527924 -0.233324 11.000000 -1.200000 AFIX 0 C7 1 0.260229 0.423244 -0.060849 11.000000 0.023990 0.022870 = 0.027770 -0.002170 0.008950 -0.003660 C8 1 0.230213 0.434541 0.008189 11.000000 0.019880 0.026540 = 0.026130 -0.001660 0.003630 -0.001450 C9 1 0.315729 0.366715 -0.031204 11.000000 0.029010 0.027500 = 0.031880 0.000530 0.010290 0.002740 AFIX 137 H9A 2 0.335136 0.355083 -0.074599 11.000000 -1.500000 H9B 2 0.306673 0.304151 -0.009562 11.000000 -1.500000 H9C 2 0.341110 0.404517 0.009634 11.000000 -1.500000 AFIX 0 C10 1 0.219997 0.372171 -0.127702 11.000000 0.032270 0.035130 = 0.029230 -0.006980 0.007430 -0.007410 AFIX 137 H10A 2 0.185971 0.412956 -0.146335 11.000000 -1.500000 H10B 2 0.207988 0.309517 -0.109441 11.000000 -1.500000 H10C 2 0.240028 0.361027 -0.170544 11.000000 -1.500000 AFIX 0 C11 1 0.208879 0.551681 0.102657 11.000000 0.019650 0.024170 = 0.023650 -0.002560 0.003300 -0.000550 C12 1 0.185820 0.650153 0.189634 11.000000 0.018750 0.024910 = 0.024700 -0.001760 0.001490 0.001280 C13 1 0.160468 0.565538 0.210742 11.000000 0.019400 0.022180 = 0.024570 -0.001540 0.001260 0.002030 C14 1 0.128260 0.564263 0.268934 11.000000 0.024900 0.022530 = 0.028470 0.000300 0.005570 -0.000400 AFIX 43 H14 2 0.111267 0.505978 0.282841 11.000000 -1.200000 AFIX 0 C15 1 0.122268 0.652226 0.305474 11.000000 0.022650 0.027620 = 0.025420 -0.002090 0.006050 0.002040 C16 1 0.148859 0.736953 0.286356 11.000000 0.025690 0.023180 = 0.033950 -0.006080 0.007940 0.000650 AFIX 43 H16 2 0.145045 0.795748 0.313516 11.000000 -1.200000 AFIX 0 C17 1 0.180338 0.736690 0.229109 11.000000 0.023400 0.024760 = 0.032530 -0.000750 0.004300 -0.001990 AFIX 43 H17 2 0.198203 0.794751 0.216478 11.000000 -1.200000 AFIX 0 C18 1 0.055154 0.585342 0.375139 11.000000 0.030570 0.025490 = 0.030240 -0.000710 0.010380 0.000270 AFIX 23 H18A 2 0.079547 0.529434 0.397410 11.000000 -1.200000 H18B 2 0.029842 0.564357 0.325393 11.000000 -1.200000 AFIX 0 C19 1 0.019356 0.619110 0.431656 11.000000 0.035200 0.033240 = 0.032250 -0.003800 0.011170 -0.004990 AFIX 137 H19A 2 0.044779 0.637475 0.481306 11.000000 -1.500000 H19B 2 -0.006228 0.566256 0.440751 11.000000 -1.500000 H19C 2 -0.003786 0.675581 0.409701 11.000000 -1.500000 AFIX 0 C20 1 0.006315 0.153559 0.444577 11.000000 0.030670 0.016540 = 0.025270 -0.004970 0.008110 0.000020 C21 1 0.042204 0.121531 0.513078 11.000000 0.023870 0.023180 = 0.029180 -0.001570 0.004230 0.004260 AFIX 43 H21 2 0.082572 0.116566 0.516356 11.000000 -1.200000 AFIX 0 C22 1 0.018907 0.096878 0.576544 11.000000 0.029970 0.023360 = 0.024470 -0.001960 0.003400 0.003510 AFIX 43 H22 2 0.043086 0.075197 0.623875 11.000000 -1.200000 AFIX 0 C23 1 -0.039888 0.104117 0.570378 11.000000 0.035350 0.016840 = 0.030040 -0.005690 0.011880 -0.000750 C24 1 -0.075712 0.138076 0.503126 11.000000 0.023760 0.021720 = 0.035800 -0.004390 0.005840 0.000160 AFIX 43 H24 2 -0.115950 0.144358 0.500433 11.000000 -1.200000 AFIX 0 C25 1 -0.052455 0.162835 0.439775 11.000000 0.026160 0.022880 = 0.027100 -0.003090 -0.001520 -0.000680 AFIX 43 H25 2 -0.076664 0.186159 0.393035 11.000000 -1.200000 AFIX 0 C26 1 0.047936 0.265489 0.362638 11.000000 0.028440 0.019480 = 0.027830 -0.000530 0.005550 0.000110 C27 1 0.078689 0.251897 0.294510 11.000000 0.030860 0.024150 = 0.025120 0.001530 0.001500 0.000720 C28 1 0.091403 0.304991 0.431869 11.000000 0.028640 0.027520 = 0.029020 -0.003430 0.004360 0.000420 AFIX 137 H28A 2 0.071873 0.320452 0.474484 11.000000 -1.500000 H28B 2 0.109160 0.364164 0.416197 11.000000 -1.500000 H28C 2 0.121282 0.255899 0.449693 11.000000 -1.500000 AFIX 0 C29 1 -0.003128 0.332862 0.337360 11.000000 0.031530 0.026470 = 0.037390 0.003080 0.002970 0.000580 AFIX 137 H29A 2 -0.031992 0.300981 0.296716 11.000000 -1.500000 H29B 2 0.009699 0.393363 0.316569 11.000000 -1.500000 H29C 2 -0.020143 0.347850 0.382433 11.000000 -1.500000 AFIX 0 C30 1 0.108767 0.127699 0.211571 11.000000 0.027220 0.028480 = 0.021110 0.001970 0.002410 -0.001460 C31 1 0.140394 0.023174 0.135519 11.000000 0.026050 0.026200 = 0.021010 0.003570 0.001880 0.000080 C32 1 0.167647 0.106378 0.114945 11.000000 0.028480 0.025610 = 0.021730 0.002960 0.001640 0.002180 C33 1 0.202360 0.104470 0.059635 11.000000 0.027470 0.028290 = 0.026010 0.006860 0.004490 -0.000780 AFIX 43 H33 2 0.221468 0.161302 0.047190 11.000000 -1.200000 AFIX 0 C34 1 0.207643 0.016131 0.023834 11.000000 0.026490 0.033840 = 0.023540 0.001950 0.004860 0.004240 C35 1 0.180456 -0.067979 0.043274 11.000000 0.030680 0.025230 = 0.033070 0.000420 0.007440 0.001980 AFIX 43 H35 2 0.185152 -0.127884 0.018088 11.000000 -1.200000 AFIX 0 C36 1 0.146999 -0.064654 0.098531 11.000000 0.030460 0.025590 = 0.029510 0.001390 0.006360 -0.002470 AFIX 43 H36 2 0.128499 -0.121932 0.111397 11.000000 -1.200000 AFIX 0 C37 1 0.261433 0.086636 -0.062731 11.000000 0.036040 0.033600 = 0.044650 0.004440 0.018220 0.001690 AFIX 23 H37A 2 0.291057 0.117431 -0.021439 11.000000 -1.200000 H37B 2 0.230417 0.134668 -0.081189 11.000000 -1.200000 AFIX 0 C38 1 0.287804 0.053597 -0.129835 11.000000 0.044210 0.038440 = 0.045620 0.004030 0.022820 -0.002090 AFIX 137 H38A 2 0.318641 0.006593 -0.110660 11.000000 -1.500000 H38B 2 0.303761 0.110015 -0.152357 11.000000 -1.500000 H38C 2 0.258115 0.022753 -0.170012 11.000000 -1.500000 AFIX 0 MOLE 1 C39 1 0.615845 0.168088 0.176449 11.000000 0.027900 0.017270 = 0.022350 0.000460 0.010380 0.000960 C40 1 0.672620 0.198634 0.189759 11.000000 0.027720 0.024240 = 0.022920 0.001460 0.004400 -0.000230 AFIX 43 H40 2 0.694142 0.206291 0.241746 11.000000 -1.200000 AFIX 0 C41 1 0.698030 0.218080 0.126600 11.000000 0.023450 0.027620 = 0.028110 0.001280 0.007370 -0.001940 AFIX 43 H41 2 0.737021 0.238975 0.135097 11.000000 -1.200000 AFIX 0 C42 1 0.666128 0.206760 0.051588 11.000000 0.029590 0.020160 = 0.025240 0.002200 0.012440 0.003180 C43 1 0.609750 0.174991 0.037812 11.000000 0.029110 0.022960 = 0.023100 0.000570 0.004400 0.003330 AFIX 43 H43 2 0.588492 0.166283 -0.014201 11.000000 -1.200000 AFIX 0 C44 1 0.584542 0.155949 0.100881 11.000000 0.021240 0.019500 = 0.028580 0.001940 0.005050 0.000680 AFIX 43 H44 2 0.545648 0.134497 0.092177 11.000000 -1.200000 AFIX 0 C45 1 0.589472 0.064720 0.277137 11.000000 0.027190 0.017370 = 0.023180 0.001580 0.008930 0.000520 C46 1 0.554533 0.079151 0.340241 11.000000 0.023700 0.022040 = 0.022090 -0.000850 0.004680 -0.000290 C47 1 0.650435 0.037408 0.317238 11.000000 0.028170 0.029400 = 0.027340 0.001460 0.008370 0.003310 AFIX 137 H47A 2 0.673643 0.027017 0.277753 11.000000 -1.500000 H47B 2 0.649705 -0.022603 0.347414 11.000000 -1.500000 H47C 2 0.667372 0.090151 0.352474 11.000000 -1.500000 AFIX 0 C48 1 0.561279 -0.013519 0.220743 11.000000 0.036140 0.024250 = 0.026300 0.000260 0.009430 -0.001630 AFIX 137 H48A 2 0.524298 0.010506 0.190712 11.000000 -1.500000 H48B 2 0.554783 -0.071783 0.250145 11.000000 -1.500000 H48C 2 0.586516 -0.029902 0.184886 11.000000 -1.500000 AFIX 0 C49 1 0.503171 0.202309 0.399743 11.000000 0.024550 0.021840 = 0.020000 0.001390 0.007120 0.001030 C50 1 0.460754 0.308411 0.462139 11.000000 0.023380 0.023800 = 0.019970 -0.000310 0.006290 0.000380 C51 1 0.459127 0.228315 0.510733 11.000000 0.020090 0.020920 = 0.022700 -0.002190 0.004080 -0.001390 C52 1 0.436434 0.233772 0.578121 11.000000 0.026840 0.020940 = 0.023260 0.001340 0.007910 -0.003580 AFIX 43 H52 2 0.436122 0.178797 0.611065 11.000000 -1.200000 AFIX 0 C53 1 0.414450 0.322761 0.594716 11.000000 0.025510 0.028350 = 0.021210 -0.002510 0.008640 -0.000290 C54 1 0.415902 0.403962 0.546762 11.000000 0.033560 0.023160 = 0.024570 -0.000370 0.008860 0.006560 AFIX 43 H54 2 0.400772 0.464365 0.559834 11.000000 -1.200000 AFIX 0 C55 1 0.438816 0.397721 0.481204 11.000000 0.033810 0.023160 = 0.023990 0.004510 0.008010 0.004010 AFIX 43 H55 2 0.439783 0.453335 0.449136 11.000000 -1.200000 AFIX 0 C56 1 0.388517 0.262074 0.710556 11.000000 0.047980 0.028790 = 0.030090 0.001270 0.019550 0.000020 AFIX 23 H56A 2 0.428259 0.240801 0.734043 11.000000 -1.200000 H56B 2 0.367168 0.205905 0.682981 11.000000 -1.200000 AFIX 0 C57 1 0.359141 0.298658 0.772798 11.000000 0.065570 0.031440 = 0.043520 0.003560 0.031970 0.005720 AFIX 137 H57A 2 0.379435 0.356385 0.797698 11.000000 -1.500000 H57B 2 0.359591 0.247660 0.812168 11.000000 -1.500000 H57C 2 0.319170 0.315874 0.749267 11.000000 -1.500000 AFIX 0 MOLE 2 Cl1 6 0.416895 0.603750 -0.308870 11.000000 0.043450 0.027010 = 0.031980 -0.000360 0.020480 -0.000790 Cl2 6 -0.069502 0.067186 0.648806 11.000000 0.045990 0.026330 = 0.038350 -0.000290 0.022300 0.002840 MOLE 1 Cl3 6 0.697729 0.237151 -0.026638 11.000000 0.038630 0.035010 = 0.028010 0.004830 0.016910 0.000400 MOLE 2 N1 3 0.231391 0.524916 0.038992 11.000000 0.024980 0.023750 = 0.024920 -0.002140 0.008010 -0.004770 H1A 2 0.246999 0.570824 0.017137 11.000000 -1.500000 N2 3 0.213319 0.640953 0.127077 11.000000 0.023150 0.025120 = 0.024960 -0.002080 0.005570 -0.002000 N3 3 0.079851 0.159307 0.267761 11.000000 0.032200 0.024900 = 0.024140 0.000220 0.008150 -0.002850 H3A 2 0.063126 0.116148 0.290899 11.000000 -1.500000 N4 3 0.107229 0.036864 0.191712 11.000000 0.030210 0.024730 = 0.022580 0.000630 0.005280 -0.000740 MOLE 1 N5 3 0.532144 0.169363 0.343992 11.000000 0.029880 0.021140 = 0.022030 0.003200 0.012410 0.002020 H5A 2 0.539602 0.211896 0.311376 11.000000 -1.500000 N6 3 0.486201 0.292107 0.398764 11.000000 0.028550 0.023420 = 0.021860 0.000890 0.009280 0.003310 MOLE 2 O1 4 0.272009 0.522340 -0.082516 11.000000 0.026220 0.021960 = 0.028800 -0.001870 0.011650 -0.001120 O2 4 0.208054 0.364948 0.033599 11.000000 0.039160 0.027510 = 0.037390 -0.004010 0.020480 -0.006630 O3 4 0.090194 0.664483 0.361556 11.000000 0.034560 0.024450 = 0.037730 -0.007110 0.016470 -0.002300 O4 4 0.028996 0.168238 0.378561 11.000000 0.035820 0.020680 = 0.023980 -0.002750 0.009000 -0.001110 O5 4 0.100777 0.320353 0.267633 11.000000 0.050660 0.025260 = 0.038420 0.001270 0.017350 -0.004150 O6 4 0.238918 0.003155 -0.033387 11.000000 0.042250 0.028410 = 0.038030 -0.000070 0.018320 -0.000090 MOLE 1 O7 4 0.588431 0.158525 0.238602 11.000000 0.029620 0.019200 = 0.023780 0.001740 0.013360 0.001530 O8 4 0.548089 0.013062 0.384543 11.000000 0.040820 0.022110 = 0.030160 0.004260 0.017600 0.002650 O9 4 0.389620 0.339970 0.657520 11.000000 0.047140 0.024160 = 0.030910 -0.000040 0.020980 0.005190 MOLE 2 S1 5 0.173180 0.468813 0.151641 11.000000 0.024400 0.022040 = 0.025650 -0.002870 0.008080 -0.001170 S2 5 0.149743 0.206748 0.166547 11.000000 0.036150 0.022740 = 0.026180 0.002190 0.008680 -0.001200 MOLE 1 S3 5 0.490138 0.127530 0.474951 11.000000 0.026530 0.018800 = 0.021810 0.000370 0.009870 0.000350 Q1 1 0.739100 0.278900 -0.016700 11.000000 0.050000 0.36 Q2 1 0.461500 0.179100 0.484400 11.000000 0.050000 0.31 Q3 1 0.160100 0.515300 0.185500 11.000000 0.050000 0.31 Q4 1 0.242400 0.396700 -0.099500 11.000000 0.050000 0.30 Q5 1 0.496000 0.161800 0.430900 11.000000 0.050000 0.30 HKLF 4 END ; # Attachment 'Compound 5.CIF' data_8hugotm _database_code_depnum_ccdc_archive 'CCDC 827872' #TrackingRef 'Compound 5.CIF' _audit_update_record ; 2011-10-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-chloro-1,3-benzothiazole-2-yl _chemical_melting_point 419 _chemical_formula_moiety 'C17 H14 Cl2 N2 O2 S, C H4 O' _chemical_formula_sum 'C18 H18 Cl2 N2 O3 S' _chemical_formula_weight 413.30 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2962(7) _cell_length_b 9.8387(10) _cell_length_c 13.9567(14) _cell_angle_alpha 77.188(2) _cell_angle_beta 84.710(2) _cell_angle_gamma 76.498(2) _cell_volume 949.08(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7677 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8910 _exptl_absorpt_correction_T_max 0.9114 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0. _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9171 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3333 _reflns_number_gt 3093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0411P)^2^+0.3454P] 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 3333 _refine_ls_number_parameters 244 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 S1 S 0.30907(5) 0.40686(4) 0.53130(3) 0.02398(12) Uani 1 1 d . . . Cl2 Cl 0.10015(6) 0.78576(5) 0.18423(3) 0.03887(14) Uani 1 1 d . . . Cl1 Cl 0.30761(7) -0.66040(5) 0.99371(4) 0.04345(15) Uani 1 1 d . . . O2 O 0.44690(18) 0.23914(12) 0.69645(9) 0.0357(3) Uani 1 1 d . . . O1 O 0.30772(16) -0.08775(12) 0.75528(9) 0.0330(3) Uani 1 1 d . . . N1 N 0.27021(18) 0.13686(13) 0.62066(10) 0.0249(3) Uani 1 1 d D . . H1 H 0.224(2) 0.0633(12) 0.6226(14) 0.037 Uiso 1 1 d D . . C4 C 0.3138(2) -0.49058(17) 0.92452(12) 0.0292(4) Uani 1 1 d . . . N2 N 0.13711(18) 0.24077(14) 0.46835(9) 0.0246(3) Uani 1 1 d . . . C14 C 0.2018(2) 0.59963(16) 0.35316(11) 0.0256(3) Uani 1 1 d . . . H14 H 0.2611 0.6688 0.3673 0.031 Uiso 1 1 calc R . . C11 C 0.2310(2) 0.24856(15) 0.54092(11) 0.0221(3) Uani 1 1 d . . . C12 C 0.1198(2) 0.36576(16) 0.39699(11) 0.0231(3) Uani 1 1 d . . . C17 C 0.0269(2) 0.39398(18) 0.30936(12) 0.0285(4) Uani 1 1 d . . . H17 H -0.0311 0.3249 0.2941 0.034 Uiso 1 1 calc R . . C13 C 0.2055(2) 0.46927(16) 0.41770(11) 0.0226(3) Uani 1 1 d . . . C15 C 0.1079(2) 0.62381(17) 0.26764(12) 0.0274(3) Uani 1 1 d . . . C1 C 0.3180(2) -0.22222(17) 0.81425(12) 0.0273(3) Uani 1 1 d . . . C16 C 0.0205(2) 0.52352(18) 0.24513(12) 0.0293(4) Uani 1 1 d . . . H16 H -0.0435 0.5445 0.1856 0.035 Uiso 1 1 calc R . . C6 C 0.4271(2) -0.34179(18) 0.78401(13) 0.0326(4) Uani 1 1 d . . . H6 H 0.5037 -0.3310 0.7252 0.039 Uiso 1 1 calc R . . C8 C 0.3835(2) 0.13588(17) 0.69371(12) 0.0272(4) Uani 1 1 d . . . C7 C 0.4379(2) -0.00396(17) 0.76918(12) 0.0281(4) Uani 1 1 d . . . C5 C 0.4249(2) -0.47732(18) 0.83938(13) 0.0339(4) Uani 1 1 d . . . H5 H 0.4991 -0.5597 0.8188 0.041 Uiso 1 1 calc R . . C2 C 0.2055(2) -0.23841(19) 0.89915(14) 0.0354(4) Uani 1 1 d . . . H2A H 0.1284 -0.1566 0.9192 0.042 Uiso 1 1 calc R . . C10 C 0.6403(2) -0.07398(19) 0.74413(14) 0.0362(4) Uani 1 1 d . . . H10A H 0.6800 -0.1633 0.7921 0.054 Uiso 1 1 calc R . . H10B H 0.7231 -0.0093 0.7461 0.054 Uiso 1 1 calc R . . H10C H 0.6483 -0.0944 0.6781 0.054 Uiso 1 1 calc R . . C3 C 0.2040(3) -0.37276(19) 0.95518(13) 0.0359(4) Uani 1 1 d . . . H3 H 0.1281 -0.3837 1.0142 0.043 Uiso 1 1 calc R . . C9 C 0.4185(3) 0.02723(18) 0.87166(12) 0.0352(4) Uani 1 1 d . . . H9A H 0.2873 0.0732 0.8855 0.053 Uiso 1 1 calc R . . H9B H 0.5011 0.0911 0.8759 0.053 Uiso 1 1 calc R . . H9C H 0.4545 -0.0624 0.9199 0.053 Uiso 1 1 calc R . . O3 O 0.87572(17) 0.09009(12) 0.42088(9) 0.0332(3) Uani 1 1 d D . . H3A H 0.9741(17) 0.106(2) 0.4390(15) 0.050 Uiso 1 1 d D . . C18 C 0.7192(3) 0.1677(2) 0.46716(14) 0.0417(5) Uani 1 1 d . . . H18A H 0.7297 0.1391 0.5387 0.063 Uiso 1 1 calc R . . H18B H 0.6031 0.1479 0.4488 0.063 Uiso 1 1 calc R . . H18C H 0.7159 0.2701 0.4462 0.063 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 S1 0.0278(2) 0.0207(2) 0.0256(2) -0.00407(15) -0.00556(16) -0.00846(15) Cl2 0.0481(3) 0.0319(2) 0.0343(3) 0.00504(18) -0.0096(2) -0.01265(19) Cl1 0.0521(3) 0.0310(2) 0.0462(3) 0.00754(19) -0.0132(2) -0.0174(2) O2 0.0467(7) 0.0277(6) 0.0369(7) -0.0014(5) -0.0149(6) -0.0164(5) O1 0.0407(7) 0.0263(6) 0.0338(7) 0.0021(5) -0.0145(5) -0.0137(5) N1 0.0298(7) 0.0207(7) 0.0261(7) -0.0031(5) -0.0041(6) -0.0097(5) C4 0.0309(9) 0.0268(8) 0.0308(9) 0.0008(7) -0.0095(7) -0.0112(7) N2 0.0273(7) 0.0236(7) 0.0250(7) -0.0056(5) -0.0021(5) -0.0090(5) C14 0.0263(8) 0.0241(8) 0.0278(9) -0.0064(6) -0.0011(7) -0.0071(6) C11 0.0222(7) 0.0208(7) 0.0251(8) -0.0064(6) 0.0008(6) -0.0071(6) C12 0.0231(7) 0.0239(8) 0.0233(8) -0.0061(6) 0.0014(6) -0.0069(6) C17 0.0312(8) 0.0316(9) 0.0268(8) -0.0074(7) -0.0036(7) -0.0130(7) C13 0.0216(7) 0.0242(8) 0.0224(8) -0.0063(6) -0.0012(6) -0.0041(6) C15 0.0275(8) 0.0266(8) 0.0262(8) -0.0026(6) 0.0010(7) -0.0060(6) C1 0.0305(8) 0.0249(8) 0.0274(8) -0.0004(6) -0.0100(7) -0.0091(7) C16 0.0297(8) 0.0358(9) 0.0236(8) -0.0056(7) -0.0031(7) -0.0094(7) C6 0.0388(10) 0.0333(9) 0.0282(9) -0.0082(7) 0.0042(7) -0.0134(7) C8 0.0288(8) 0.0265(8) 0.0272(8) -0.0054(7) -0.0030(7) -0.0073(7) C7 0.0335(9) 0.0248(8) 0.0282(9) -0.0045(7) -0.0073(7) -0.0096(7) C5 0.0343(9) 0.0277(9) 0.0410(10) -0.0092(7) 0.0000(8) -0.0078(7) C2 0.0334(9) 0.0303(9) 0.0422(10) -0.0104(8) 0.0037(8) -0.0058(7) C10 0.0368(9) 0.0308(9) 0.0399(10) -0.0055(7) -0.0056(8) -0.0055(7) C3 0.0392(10) 0.0376(10) 0.0323(9) -0.0071(8) 0.0065(8) -0.0144(8) C9 0.0471(10) 0.0309(9) 0.0287(9) -0.0053(7) -0.0092(8) -0.0083(8) O3 0.0322(6) 0.0303(6) 0.0426(7) -0.0129(5) -0.0054(5) -0.0111(5) C18 0.0429(11) 0.0462(11) 0.0435(11) -0.0188(9) 0.0031(9) -0.0173(9) _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 S1 C13 1.7418(15) . ? S1 C11 1.7536(15) . ? Cl2 C15 1.7449(16) . ? Cl1 C4 1.7430(16) . ? O2 C8 1.220(2) . ? O1 C1 1.3840(19) . ? O1 C7 1.4459(19) . ? N1 C8 1.367(2) . ? N1 C11 1.378(2) . ? N1 H1 0.8599(10) . ? C4 C5 1.374(2) . ? C4 C3 1.375(2) . ? N2 C11 1.299(2) . ? N2 C12 1.3883(19) . ? C14 C15 1.378(2) . ? C14 C13 1.390(2) . ? C14 H14 0.9500 . ? C12 C17 1.395(2) . ? C12 C13 1.405(2) . ? C17 C16 1.379(2) . ? C17 H17 0.9500 . ? C15 C16 1.396(2) . ? C1 C2 1.379(2) . ? C1 C6 1.384(2) . ? C16 H16 0.9500 . ? C6 C5 1.388(2) . ? C6 H6 0.9500 . ? C8 C7 1.530(2) . ? C7 C9 1.516(2) . ? C7 C10 1.521(2) . ? C5 H5 0.9500 . ? C2 C3 1.380(2) . ? C2 H2A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C3 H3 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O3 C18 1.407(2) . ? O3 H3A 0.8399(10) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 C13 S1 C11 88.24(7) . . ? C1 O1 C7 119.05(12) . . ? C8 N1 C11 123.13(13) . . ? C8 N1 H1 119.3(13) . . ? C11 N1 H1 117.6(13) . . ? C5 C4 C3 121.40(16) . . ? C5 C4 Cl1 119.35(13) . . ? C3 C4 Cl1 119.23(13) . . ? C11 N2 C12 110.17(13) . . ? C15 C14 C13 116.86(14) . . ? C15 C14 H14 121.6 . . ? C13 C14 H14 121.6 . . ? N2 C11 N1 121.57(13) . . ? N2 C11 S1 116.74(12) . . ? N1 C11 S1 121.68(11) . . ? N2 C12 C17 125.48(14) . . ? N2 C12 C13 115.12(13) . . ? C17 C12 C13 119.40(14) . . ? C16 C17 C12 119.18(15) . . ? C16 C17 H17 120.4 . . ? C12 C17 H17 120.4 . . ? C14 C13 C12 122.01(14) . . ? C14 C13 S1 128.26(12) . . ? C12 C13 S1 109.73(11) . . ? C14 C15 C16 122.52(15) . . ? C14 C15 Cl2 118.47(12) . . ? C16 C15 Cl2 119.00(13) . . ? C2 C1 O1 119.66(15) . . ? C2 C1 C6 119.69(15) . . ? O1 C1 C6 120.37(15) . . ? C17 C16 C15 120.02(15) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C1 C6 C5 120.22(16) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O2 C8 N1 121.95(15) . . ? O2 C8 C7 120.83(14) . . ? N1 C8 C7 117.12(13) . . ? O1 C7 C9 112.37(14) . . ? O1 C7 C10 111.36(13) . . ? C9 C7 C10 111.24(14) . . ? O1 C7 C8 104.36(12) . . ? C9 C7 C8 109.56(13) . . ? C10 C7 C8 107.62(13) . . ? C4 C5 C6 118.99(16) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C2 C3 120.44(16) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C3 C2 119.24(16) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C18 O3 H3A 108.2(15) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C12 N2 C11 N1 -178.95(13) . . . . ? C12 N2 C11 S1 -0.08(17) . . . . ? C8 N1 C11 N2 173.61(14) . . . . ? C8 N1 C11 S1 -5.2(2) . . . . ? C13 S1 C11 N2 -0.20(12) . . . . ? C13 S1 C11 N1 178.68(13) . . . . ? C11 N2 C12 C17 -179.81(15) . . . . ? C11 N2 C12 C13 0.41(18) . . . . ? N2 C12 C17 C16 179.85(14) . . . . ? C13 C12 C17 C16 -0.4(2) . . . . ? C15 C14 C13 C12 0.6(2) . . . . ? C15 C14 C13 S1 -179.33(12) . . . . ? N2 C12 C13 C14 179.50(13) . . . . ? C17 C12 C13 C14 -0.3(2) . . . . ? N2 C12 C13 S1 -0.55(16) . . . . ? C17 C12 C13 S1 179.66(12) . . . . ? C11 S1 C13 C14 -179.65(15) . . . . ? C11 S1 C13 C12 0.40(11) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C13 C14 C15 Cl2 -179.80(11) . . . . ? C7 O1 C1 C2 93.66(18) . . . . ? C7 O1 C1 C6 -92.36(18) . . . . ? C12 C17 C16 C15 0.7(2) . . . . ? C14 C15 C16 C17 -0.4(2) . . . . ? Cl2 C15 C16 C17 179.14(12) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? O1 C1 C6 C5 -174.68(15) . . . . ? C11 N1 C8 O2 5.3(2) . . . . ? C11 N1 C8 C7 -171.08(13) . . . . ? C1 O1 C7 C9 -60.58(19) . . . . ? C1 O1 C7 C10 64.98(18) . . . . ? C1 O1 C7 C8 -179.20(13) . . . . ? O2 C8 C7 O1 168.40(14) . . . . ? N1 C8 C7 O1 -15.15(19) . . . . ? O2 C8 C7 C9 47.9(2) . . . . ? N1 C8 C7 C9 -135.66(15) . . . . ? O2 C8 C7 C10 -73.19(19) . . . . ? N1 C8 C7 C10 103.26(16) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? Cl1 C4 C5 C6 179.13(13) . . . . ? C1 C6 C5 C4 -0.3(3) . . . . ? O1 C1 C2 C3 175.40(15) . . . . ? C6 C1 C2 C3 1.4(3) . . . . ? C5 C4 C3 C2 0.1(3) . . . . ? Cl1 C4 C3 C2 -178.46(14) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.269 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.071 _iucr_refine_instructions_details ; TITL 8hugotm in P-1 CELL 0.71073 7.2962 9.8387 13.9567 77.188 84.710 76.498 ZERR 2.00 0.0007 0.0010 0.0014 0.002 0.002 0.002 LATT 1 SFAC C H N O S Cl UNIT 36 36 4 6 2 4 OMIT -3.00 50.00 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 DFIX 0.84 0.001 O3 H3A DFIX 0.86 0.001 N1 H1 SIZE 0.20 0.23 0.25 CONF WGHT 0.041100 0.345400 FVAR 0.661730 TEMP -100.5 MOLE 1 S1 5 0.309067 0.406865 0.531303 11.000000 0.027780 0.020720 = 0.025550 -0.004070 -0.005560 -0.008460 Cl2 6 0.100147 0.785761 0.184228 11.000000 0.048130 0.031920 = 0.034330 0.005040 -0.009560 -0.012650 Cl1 6 0.307611 -0.660402 0.993714 11.000000 0.052080 0.030950 = 0.046240 0.007540 -0.013190 -0.017420 O2 4 0.446898 0.239145 0.696455 11.000000 0.046740 0.027660 = 0.036890 -0.001380 -0.014910 -0.016440 O1 4 0.307722 -0.087753 0.755278 11.000000 0.040690 0.026290 = 0.033750 0.002060 -0.014550 -0.013730 N1 3 0.270211 0.136856 0.620662 11.000000 0.029810 0.020650 = 0.026130 -0.003080 -0.004140 -0.009720 H1 2 0.224257 0.063333 0.622589 11.000000 -1.500000 C4 1 0.313806 -0.490576 0.924521 11.000000 0.030860 0.026770 = 0.030750 0.000800 -0.009500 -0.011190 N2 3 0.137112 0.240769 0.468350 11.000000 0.027250 0.023600 = 0.025050 -0.005560 -0.002110 -0.009010 C14 1 0.201760 0.599631 0.353158 11.000000 0.026290 0.024050 = 0.027760 -0.006410 -0.001150 -0.007060 AFIX 43 H14 2 0.261081 0.668782 0.367348 11.000000 -1.200000 AFIX 0 C11 1 0.231036 0.248561 0.540921 11.000000 0.022160 0.020790 = 0.025120 -0.006440 0.000800 -0.007120 C12 1 0.119769 0.365758 0.396993 11.000000 0.023110 0.023890 = 0.023330 -0.006080 0.001380 -0.006910 C17 1 0.026944 0.393983 0.309358 11.000000 0.031200 0.031560 = 0.026830 -0.007430 -0.003560 -0.012990 AFIX 43 H17 2 -0.031094 0.324861 0.294100 11.000000 -1.200000 AFIX 0 C13 1 0.205535 0.469266 0.417704 11.000000 0.021630 0.024160 = 0.022380 -0.006290 -0.001190 -0.004110 C15 1 0.107926 0.623810 0.267638 11.000000 0.027490 0.026610 = 0.026240 -0.002600 0.000980 -0.005960 C1 1 0.317996 -0.222224 0.814254 11.000000 0.030480 0.024860 = 0.027400 -0.000440 -0.009970 -0.009120 C16 1 0.020476 0.523516 0.245130 11.000000 0.029660 0.035800 = 0.023610 -0.005640 -0.003140 -0.009360 AFIX 43 H16 2 -0.043526 0.544459 0.185556 11.000000 -1.200000 AFIX 0 C6 1 0.427074 -0.341788 0.784007 11.000000 0.038830 0.033340 = 0.028160 -0.008210 0.004230 -0.013360 AFIX 43 H6 2 0.503652 -0.331027 0.725154 11.000000 -1.200000 AFIX 0 C8 1 0.383496 0.135876 0.693706 11.000000 0.028750 0.026520 = 0.027150 -0.005400 -0.003050 -0.007260 C7 1 0.437949 -0.003963 0.769176 11.000000 0.033490 0.024810 = 0.028190 -0.004540 -0.007280 -0.009580 C5 1 0.424921 -0.477324 0.839382 11.000000 0.034290 0.027730 = 0.040970 -0.009200 0.000020 -0.007820 AFIX 43 H5 2 0.499118 -0.559688 0.818755 11.000000 -1.200000 AFIX 0 C2 1 0.205481 -0.238410 0.899154 11.000000 0.033390 0.030290 = 0.042160 -0.010370 0.003710 -0.005850 AFIX 43 H2A 2 0.128445 -0.156558 0.919219 11.000000 -1.200000 AFIX 0 C10 1 0.640348 -0.073980 0.744127 11.000000 0.036830 0.030800 = 0.039910 -0.005520 -0.005610 -0.005490 AFIX 137 H10A 2 0.680020 -0.163308 0.792096 11.000000 -1.500000 H10B 2 0.723108 -0.009298 0.746062 11.000000 -1.500000 H10C 2 0.648306 -0.094440 0.678087 11.000000 -1.500000 AFIX 0 C3 1 0.204040 -0.372759 0.955183 11.000000 0.039230 0.037570 = 0.032340 -0.007080 0.006540 -0.014430 AFIX 43 H3 2 0.128094 -0.383715 1.014249 11.000000 -1.200000 AFIX 0 C9 1 0.418512 0.027227 0.871664 11.000000 0.047080 0.030850 = 0.028660 -0.005260 -0.009200 -0.008280 AFIX 137 H9A 2 0.287322 0.073150 0.885516 11.000000 -1.500000 H9B 2 0.501097 0.091061 0.875850 11.000000 -1.500000 H9C 2 0.454549 -0.062361 0.919891 11.000000 -1.500000 AFIX 0 O3 4 0.875725 0.090087 0.420875 11.000000 0.032240 0.030270 = 0.042560 -0.012940 -0.005390 -0.011110 H3A 2 0.974056 0.105860 0.438974 11.000000 -1.500000 C18 1 0.719233 0.167679 0.467157 11.000000 0.042930 0.046180 = 0.043490 -0.018770 0.003140 -0.017260 AFIX 137 H18A 2 0.729716 0.139130 0.538661 11.000000 -1.500000 H18B 2 0.603112 0.147865 0.448835 11.000000 -1.500000 H18C 2 0.715865 0.270088 0.446213 11.000000 -1.500000 AFIX 0 Q1 1 0.243900 0.465600 0.479000 11.000000 0.050000 0.27 Q2 1 0.364500 0.102300 0.878400 11.000000 0.050000 0.25 Q3 1 0.326200 0.034300 0.895000 11.000000 0.050000 0.23 Q4 1 0.146900 -0.197700 0.898000 11.000000 0.050000 0.23 Q5 1 0.412800 0.024100 0.825800 11.000000 0.050000 0.22 HKLF 4 END ; # Attachment 'Compound 6.CIF' data_3hugotm _database_code_depnum_ccdc_archive 'CCDC 827873' #TrackingRef 'Compound 6.CIF' _audit_update_record ; 2011-10-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-nitro-1,3-benzothiazole-2-yl _chemical_melting_point 461 _chemical_formula_moiety 'C17 H14 Cl N3 O4 S' _chemical_formula_sum 'C17 H14 Cl N3 O4 S' _chemical_formula_weight 391.82 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.395(2) _cell_length_b 7.653(2) _cell_length_c 15.958(4) _cell_angle_alpha 90.156(5) _cell_angle_beta 96.693(4) _cell_angle_gamma 99.998(4) _cell_volume 883.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2896 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 25.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9115 _exptl_absorpt_correction_T_max 0.9342 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8330 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3097 _reflns_number_gt 2344 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0754P)^2^+0.0037P] 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 3097 _refine_ls_number_parameters 240 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1335 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 C1 C -0.1506(3) 0.7550(3) 0.07584(15) 0.0445(6) Uani 1 1 d . . . C2 C -0.1888(4) 0.6596(3) 0.00078(16) 0.0495(7) Uani 1 1 d . . . H2 H -0.1691 0.5430 -0.0010 0.059 Uiso 1 1 calc R . . C3 C -0.2561(4) 0.7359(4) -0.07175(16) 0.0517(7) Uani 1 1 d . . . H3 H -0.2813 0.6715 -0.1225 0.062 Uiso 1 1 calc R . . C4 C -0.2856(3) 0.9070(4) -0.06840(17) 0.0500(7) Uani 1 1 d . . . C5 C -0.2476(4) 1.0035(4) 0.00650(19) 0.0571(7) Uani 1 1 d . . . H5 H -0.2685 1.1198 0.0082 0.069 Uiso 1 1 calc R . . C6 C -0.1789(4) 0.9281(4) 0.07855(17) 0.0542(7) Uani 1 1 d . . . H6 H -0.1515 0.9936 0.1290 0.065 Uiso 1 1 calc R . . C7 C -0.1847(3) 0.5810(3) 0.20305(15) 0.0452(6) Uani 1 1 d . . . C8 C -0.0676(3) 0.5939(3) 0.28928(16) 0.0445(6) Uani 1 1 d . . . C9 C -0.2265(4) 0.3888(4) 0.17403(19) 0.0680(8) Uani 1 1 d . . . H9A H -0.3045 0.3772 0.1211 0.102 Uiso 1 1 calc R . . H9B H -0.2886 0.3185 0.2153 0.102 Uiso 1 1 calc R . . H9C H -0.1131 0.3485 0.1672 0.102 Uiso 1 1 calc R . . C10 C -0.3589(4) 0.6551(4) 0.21253(19) 0.0647(8) Uani 1 1 d . . . H10A H -0.3259 0.7758 0.2330 0.097 Uiso 1 1 calc R . . H10B H -0.4282 0.5854 0.2518 0.097 Uiso 1 1 calc R . . H10C H -0.4329 0.6509 0.1587 0.097 Uiso 1 1 calc R . . C11 C 0.2339(3) 0.7207(3) 0.36337(15) 0.0408(6) Uani 1 1 d . . . C12 C 0.5059(3) 0.8064(3) 0.43397(15) 0.0414(6) Uani 1 1 d . . . C13 C 0.4162(3) 0.7152(3) 0.49797(15) 0.0396(6) Uani 1 1 d . . . C14 C 0.5077(3) 0.7007(3) 0.57795(15) 0.0445(6) Uani 1 1 d . . . H14 H 0.4490 0.6389 0.6202 0.053 Uiso 1 1 calc R . . C15 C 0.6893(3) 0.7822(3) 0.59151(16) 0.0445(6) Uani 1 1 d . . . C16 C 0.7817(3) 0.8739(4) 0.52985(17) 0.0509(7) Uani 1 1 d . . . H16 H 0.9050 0.9273 0.5420 0.061 Uiso 1 1 calc R . . C17 C 0.6896(3) 0.8854(4) 0.45033(16) 0.0522(7) Uani 1 1 d . . . H17 H 0.7503 0.9456 0.4082 0.063 Uiso 1 1 calc R . . Cl1 Cl -0.36677(10) 1.00492(11) -0.16041(5) 0.0714(3) Uani 1 1 d . . . N1 N 0.1005(3) 0.6999(3) 0.29384(13) 0.0450(5) Uani 1 1 d D . . H1A H 0.131(4) 0.748(3) 0.2478(10) 0.067 Uiso 1 1 d D . . N2 N 0.3972(3) 0.8085(3) 0.35724(12) 0.0443(5) Uani 1 1 d . . . N3 N 0.7932(3) 0.7690(3) 0.67427(14) 0.0552(6) Uani 1 1 d . . . O1 O -0.0685(2) 0.6851(2) 0.14759(11) 0.0538(5) Uani 1 1 d . . . O2 O -0.1232(3) 0.5143(3) 0.34927(12) 0.0653(6) Uani 1 1 d . . . O3 O 0.9391(3) 0.8718(3) 0.69251(14) 0.0784(7) Uani 1 1 d . . . O4 O 0.7302(3) 0.6556(3) 0.72150(13) 0.0714(6) Uani 1 1 d . . . S1 S 0.18829(8) 0.62877(8) 0.45996(4) 0.0446(2) 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 C1 0.0374(13) 0.0553(16) 0.0375(15) 0.0069(12) 0.0026(11) 0.0001(11) C2 0.0546(16) 0.0493(16) 0.0443(16) 0.0017(12) 0.0024(12) 0.0102(12) C3 0.0562(16) 0.0590(17) 0.0365(15) 0.0016(12) -0.0010(12) 0.0045(13) C4 0.0386(14) 0.0591(18) 0.0507(17) 0.0158(14) 0.0045(12) 0.0040(12) C5 0.0618(17) 0.0483(16) 0.0631(19) 0.0106(14) 0.0161(15) 0.0089(13) C6 0.0604(18) 0.0545(18) 0.0439(16) -0.0015(13) 0.0078(13) -0.0016(13) C7 0.0402(14) 0.0518(16) 0.0409(14) 0.0060(12) 0.0025(11) 0.0022(11) C8 0.0457(15) 0.0449(14) 0.0402(15) 0.0010(12) 0.0027(12) 0.0022(11) C9 0.071(2) 0.0633(19) 0.0599(19) -0.0076(15) -0.0113(15) -0.0038(15) C10 0.0512(17) 0.084(2) 0.0628(19) 0.0190(16) 0.0120(14) 0.0192(15) C11 0.0449(14) 0.0386(13) 0.0364(14) 0.0011(11) 0.0002(11) 0.0032(11) C12 0.0416(14) 0.0443(14) 0.0364(14) -0.0006(11) 0.0027(11) 0.0041(11) C13 0.0427(13) 0.0387(13) 0.0360(13) 0.0010(10) 0.0051(11) 0.0030(11) C14 0.0527(15) 0.0436(14) 0.0361(14) 0.0056(11) 0.0063(12) 0.0048(12) C15 0.0445(14) 0.0484(15) 0.0394(14) 0.0002(11) -0.0014(11) 0.0094(12) C16 0.0363(13) 0.0631(17) 0.0493(16) 0.0030(13) 0.0016(12) -0.0001(12) C17 0.0435(14) 0.0653(17) 0.0435(16) 0.0069(13) 0.0070(12) -0.0039(13) Cl1 0.0601(5) 0.0858(6) 0.0681(5) 0.0346(4) 0.0032(4) 0.0149(4) N1 0.0426(12) 0.0494(13) 0.0370(12) 0.0054(10) -0.0027(10) -0.0034(10) N2 0.0422(12) 0.0511(13) 0.0356(12) 0.0062(10) 0.0027(9) -0.0022(10) N3 0.0598(15) 0.0593(15) 0.0445(14) 0.0010(12) -0.0054(11) 0.0122(12) O1 0.0404(10) 0.0783(13) 0.0394(10) 0.0119(9) 0.0011(8) 0.0033(9) O2 0.0566(12) 0.0844(14) 0.0439(11) 0.0167(10) 0.0011(9) -0.0155(10) O3 0.0624(14) 0.0910(16) 0.0677(15) 0.0035(12) -0.0229(11) -0.0051(12) O4 0.0888(16) 0.0747(14) 0.0450(12) 0.0134(11) -0.0055(11) 0.0075(12) S1 0.0424(4) 0.0491(4) 0.0373(4) 0.0064(3) 0.0028(3) -0.0050(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 C1 C2 1.375(3) . ? C1 C6 1.378(4) . ? C1 O1 1.385(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.366(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(4) . ? C4 Cl1 1.742(3) . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.449(3) . ? C7 C9 1.509(4) . ? C7 C10 1.517(4) . ? C7 C8 1.531(3) . ? C8 O2 1.210(3) . ? C8 N1 1.355(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N2 1.291(3) . ? C11 N1 1.385(3) . ? C11 S1 1.740(2) . ? C12 C17 1.382(3) . ? C12 N2 1.386(3) . ? C12 C13 1.404(3) . ? C13 C14 1.387(3) . ? C13 S1 1.738(2) . ? C14 C15 1.371(3) . ? C14 H14 0.9300 . ? C15 C16 1.386(3) . ? C15 N3 1.461(3) . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N1 H1A 0.8599(11) . ? N3 O4 1.218(3) . ? N3 O3 1.224(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 119.9(2) . . ? C2 C1 O1 120.9(2) . . ? C6 C1 O1 119.0(2) . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 Cl1 119.4(2) . . ? C5 C4 Cl1 119.9(2) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 C9 110.1(2) . . ? O1 C7 C10 112.6(2) . . ? C9 C7 C10 112.2(2) . . ? O1 C7 C8 105.16(19) . . ? C9 C7 C8 108.2(2) . . ? C10 C7 C8 108.2(2) . . ? O2 C8 N1 122.6(2) . . ? O2 C8 C7 121.6(2) . . ? N1 C8 C7 115.8(2) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 N1 120.0(2) . . ? N2 C11 S1 118.38(18) . . ? N1 C11 S1 121.59(18) . . ? C17 C12 N2 125.1(2) . . ? C17 C12 C13 119.8(2) . . ? N2 C12 C13 115.1(2) . . ? C14 C13 C12 121.7(2) . . ? C14 C13 S1 128.34(19) . . ? C12 C13 S1 109.99(17) . . ? C15 C14 C13 116.5(2) . . ? C15 C14 H14 121.7 . . ? C13 C14 H14 121.7 . . ? C14 C15 C16 123.3(2) . . ? C14 C15 N3 118.8(2) . . ? C16 C15 N3 117.9(2) . . ? C17 C16 C15 119.6(2) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C12 119.2(2) . . ? C16 C17 H17 120.4 . . ? C12 C17 H17 120.4 . . ? C8 N1 C11 125.6(2) . . ? C8 N1 H1A 117(2) . . ? C11 N1 H1A 117(2) . . ? C11 N2 C12 109.1(2) . . ? O4 N3 O3 123.3(2) . . ? O4 N3 C15 118.2(2) . . ? O3 N3 C15 118.5(2) . . ? C1 O1 C7 119.12(18) . . ? C13 S1 C11 87.45(11) . . ? 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 -0.3(4) . . . . ? O1 C1 C2 C3 -174.6(2) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C2 C3 C4 Cl1 178.8(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? Cl1 C4 C5 C6 -178.2(2) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C2 C1 C6 C5 0.9(4) . . . . ? O1 C1 C6 C5 175.3(2) . . . . ? O1 C7 C8 O2 -176.9(2) . . . . ? C9 C7 C8 O2 -59.2(3) . . . . ? C10 C7 C8 O2 62.6(3) . . . . ? O1 C7 C8 N1 3.3(3) . . . . ? C9 C7 C8 N1 121.0(3) . . . . ? C10 C7 C8 N1 -117.2(2) . . . . ? C17 C12 C13 C14 -0.5(4) . . . . ? N2 C12 C13 C14 179.5(2) . . . . ? C17 C12 C13 S1 -179.7(2) . . . . ? N2 C12 C13 S1 0.3(3) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? S1 C13 C14 C15 179.99(19) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? C13 C14 C15 N3 -179.1(2) . . . . ? C14 C15 C16 C17 -0.1(4) . . . . ? N3 C15 C16 C17 178.4(2) . . . . ? C15 C16 C17 C12 0.6(4) . . . . ? N2 C12 C17 C16 179.7(2) . . . . ? C13 C12 C17 C16 -0.3(4) . . . . ? O2 C8 N1 C11 5.2(4) . . . . ? C7 C8 N1 C11 -175.0(2) . . . . ? N2 C11 N1 C8 171.7(2) . . . . ? S1 C11 N1 C8 -7.6(3) . . . . ? N1 C11 N2 C12 -178.4(2) . . . . ? S1 C11 N2 C12 1.0(3) . . . . ? C17 C12 N2 C11 179.2(2) . . . . ? C13 C12 N2 C11 -0.8(3) . . . . ? C14 C15 N3 O4 16.2(4) . . . . ? C16 C15 N3 O4 -162.4(2) . . . . ? C14 C15 N3 O3 -164.1(2) . . . . ? C16 C15 N3 O3 17.4(4) . . . . ? C2 C1 O1 C7 -89.1(3) . . . . ? C6 C1 O1 C7 96.6(3) . . . . ? C9 C7 O1 C1 87.4(3) . . . . ? C10 C7 O1 C1 -38.7(3) . . . . ? C8 C7 O1 C1 -156.2(2) . . . . ? C14 C13 S1 C11 -178.9(2) . . . . ? C12 C13 S1 C11 0.19(18) . . . . ? N2 C11 S1 C13 -0.7(2) . . . . ? N1 C11 S1 C13 178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.347 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.069 _iucr_refine_instructions_details ; TITL 3hugotm in P-1 CELL 0.71073 7.3948 7.6525 15.9577 90.156 96.693 99.998 ZERR 2.00 0.0020 0.0021 0.0044 0.005 0.004 0.004 LATT 1 SFAC C H N O S Cl UNIT 34 28 6 8 2 2 OMIT -3.00 50.00 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 CONF DFIX 0.86 0.001 N1 H1A SIZE 0.19 0.24 0.26 WGHT 0.075400 0.003700 FVAR 0.691300 TEMP 21 MOLE 1 C1 1 -0.150589 0.754951 0.075844 11.000000 0.037450 0.055290 = 0.037500 0.006920 0.002620 0.000070 C2 1 -0.188795 0.659630 0.000780 11.000000 0.054630 0.049270 = 0.044310 0.001670 0.002440 0.010230 AFIX 43 H2 2 -0.169063 0.542991 -0.001036 11.000000 -1.200000 AFIX 0 C3 1 -0.256136 0.735918 -0.071752 11.000000 0.056160 0.058950 = 0.036530 0.001570 -0.001030 0.004540 AFIX 43 H3 2 -0.281268 0.671517 -0.122530 11.000000 -1.200000 AFIX 0 C4 1 -0.285643 0.907001 -0.068396 11.000000 0.038570 0.059090 = 0.050750 0.015850 0.004530 0.004030 C5 1 -0.247594 1.003507 0.006499 11.000000 0.061770 0.048270 = 0.063140 0.010630 0.016080 0.008910 AFIX 43 H5 2 -0.268484 1.119780 0.008220 11.000000 -1.200000 AFIX 0 C6 1 -0.178887 0.928116 0.078555 11.000000 0.060400 0.054550 = 0.043870 -0.001490 0.007820 -0.001560 AFIX 43 H6 2 -0.151521 0.993579 0.129014 11.000000 -1.200000 AFIX 0 C7 1 -0.184730 0.581027 0.203052 11.000000 0.040160 0.051810 = 0.040870 0.006030 0.002460 0.002200 C8 1 -0.067615 0.593932 0.289276 11.000000 0.045650 0.044940 = 0.040240 0.000970 0.002650 0.002180 C9 1 -0.226530 0.388830 0.174030 11.000000 0.070580 0.063300 = 0.059930 -0.007620 -0.011340 -0.003820 AFIX 137 H9A 2 -0.304500 0.377211 0.121117 11.000000 -1.500000 H9B 2 -0.288573 0.318496 0.215347 11.000000 -1.500000 H9C 2 -0.113101 0.348545 0.167167 11.000000 -1.500000 AFIX 0 C10 1 -0.358911 0.655081 0.212530 11.000000 0.051190 0.084190 = 0.062800 0.018970 0.012010 0.019210 AFIX 137 H10A 2 -0.325931 0.775804 0.233041 11.000000 -1.500000 H10B 2 -0.428151 0.585367 0.251817 11.000000 -1.500000 H10C 2 -0.432875 0.650933 0.158729 11.000000 -1.500000 AFIX 0 C11 1 0.233877 0.720680 0.363367 11.000000 0.044890 0.038550 = 0.036380 0.001080 0.000200 0.003210 C12 1 0.505914 0.806407 0.433966 11.000000 0.041620 0.044300 = 0.036450 -0.000570 0.002750 0.004140 C13 1 0.416239 0.715224 0.497967 11.000000 0.042680 0.038690 = 0.035970 0.001040 0.005090 0.002970 C14 1 0.507746 0.700699 0.577950 11.000000 0.052690 0.043550 = 0.036130 0.005580 0.006300 0.004760 AFIX 43 H14 2 0.448980 0.638885 0.620161 11.000000 -1.200000 AFIX 0 C15 1 0.689298 0.782217 0.591514 11.000000 0.044520 0.048390 = 0.039370 0.000190 -0.001420 0.009350 C16 1 0.781655 0.873871 0.529845 11.000000 0.036290 0.063120 = 0.049330 0.003030 0.001640 -0.000120 AFIX 43 H16 2 0.904954 0.927256 0.542016 11.000000 -1.200000 AFIX 0 C17 1 0.689581 0.885413 0.450329 11.000000 0.043550 0.065260 = 0.043490 0.006900 0.006960 -0.003880 AFIX 43 H17 2 0.750315 0.945601 0.408250 11.000000 -1.200000 AFIX 0 Cl1 6 -0.366765 1.004924 -0.160410 11.000000 0.060100 0.085830 = 0.068070 0.034590 0.003240 0.014870 N1 3 0.100461 0.699862 0.293843 11.000000 0.042570 0.049440 = 0.037040 0.005430 -0.002700 -0.003420 H1A 2 0.131078 0.748342 0.247813 11.000000 -1.500000 N2 3 0.397174 0.808533 0.357237 11.000000 0.042200 0.051070 = 0.035580 0.006170 0.002660 -0.002230 N3 3 0.793158 0.769020 0.674268 11.000000 0.059750 0.059250 = 0.044470 0.001020 -0.005370 0.012230 O1 4 -0.068464 0.685089 0.147590 11.000000 0.040440 0.078260 = 0.039370 0.011930 0.001150 0.003250 O2 4 -0.123154 0.514295 0.349271 11.000000 0.056580 0.084420 = 0.043910 0.016670 0.001120 -0.015450 O3 4 0.939128 0.871815 0.692513 11.000000 0.062420 0.091020 = 0.067720 0.003480 -0.022950 -0.005080 O4 4 0.730156 0.655600 0.721503 11.000000 0.088810 0.074710 = 0.045030 0.013410 -0.005490 0.007500 S1 5 0.188286 0.628775 0.459960 11.000000 0.042360 0.049130 = 0.037300 0.006420 0.002820 -0.005050 Q1 1 -0.332900 1.108100 -0.121200 11.000000 0.050000 0.35 Q2 1 -0.303700 1.032100 0.001200 11.000000 0.050000 0.25 Q3 1 -0.241100 0.979200 -0.039600 11.000000 0.050000 0.24 Q4 1 -0.221400 0.827500 0.080600 11.000000 0.050000 0.23 Q5 1 -0.396600 1.112200 0.003100 11.000000 0.050000 0.23 HKLF 4 END ; data_2hugotm _database_code_depnum_ccdc_archive 'CCDC 827874' #TrackingRef 'Compompound 7.CIF' _audit_update_record ; 2011-10-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6-methanesulfonyl-1,3-benzothiazole-2-yl _chemical_melting_point 493 _chemical_formula_moiety 'C18 H17 Cl N2 O4 S2' _chemical_formula_sum 'C18 H17 Cl N2 O4 S2' _chemical_formula_weight 424.91 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' 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 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 29.002(3) _cell_length_b 8.6295(9) _cell_length_c 16.5593(18) _cell_angle_alpha 90.00 _cell_angle_beta 113.948(2) _cell_angle_gamma 90.00 _cell_volume 3787.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 5917 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8882 _exptl_absorpt_correction_T_max 0.9115 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17796 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3338 _reflns_number_gt 2688 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0623P)^2^+1.6132P] 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 3338 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 S2 S 1.15015(2) 0.45853(7) 0.48648(4) 0.0401(2) Uani 1 1 d . . . S1 S 0.99641(2) 0.78849(8) 0.52666(4) 0.0410(2) Uani 1 1 d . . . Cl1 Cl 0.73076(3) 0.89399(9) 0.84180(5) 0.0653(3) Uani 1 1 d . . . N1 N 0.95597(7) 0.7963(2) 0.65091(12) 0.0352(5) Uani 1 1 d D . . H1 H 0.9533(10) 0.753(3) 0.6957(11) 0.053 Uiso 1 1 d D . . N2 N 1.02293(7) 0.6316(2) 0.67304(12) 0.0343(5) Uani 1 1 d . . . O1 O 0.89476(6) 0.8664(2) 0.72071(12) 0.0476(5) Uani 1 1 d . . . C11 C 0.99135(8) 0.7340(3) 0.62398(14) 0.0308(5) Uani 1 1 d . . . C13 C 1.04518(8) 0.6547(3) 0.55211(14) 0.0321(5) Uani 1 1 d . . . C15 C 1.11186(9) 0.5094(3) 0.54185(15) 0.0345(5) Uani 1 1 d . . . C14 C 1.07394(9) 0.6181(3) 0.50516(15) 0.0371(6) Uani 1 1 d . . . H14 H 1.0680 0.6647 0.4512 0.045 Uiso 1 1 calc R . . C4 C 0.78033(10) 0.8851(3) 0.80777(17) 0.0454(6) Uani 1 1 d . . . O3 O 1.12739(7) 0.5153(2) 0.39775(11) 0.0569(5) Uani 1 1 d . . . C8 C 0.93039(9) 0.9297(3) 0.61907(16) 0.0407(6) Uani 1 1 d . . . C12 C 1.05452(8) 0.5851(3) 0.63366(14) 0.0316(5) Uani 1 1 d . . . O2 O 0.93363(8) 1.0010(2) 0.55813(13) 0.0627(6) Uani 1 1 d . . . O4 O 1.16230(8) 0.2979(2) 0.50124(14) 0.0602(5) Uani 1 1 d . . . C16 C 1.12212(9) 0.4418(3) 0.62398(16) 0.0420(6) Uani 1 1 d . . . H16 H 1.1482 0.3703 0.6473 0.050 Uiso 1 1 calc R . . C17 C 1.09393(9) 0.4802(3) 0.67031(16) 0.0424(6) Uani 1 1 d . . . H17 H 1.1011 0.4367 0.7255 0.051 Uiso 1 1 calc R . . C1 C 0.85677(10) 0.8757(3) 0.75102(17) 0.0416(6) Uani 1 1 d . . . C5 C 0.82442(11) 0.9624(4) 0.85455(17) 0.0528(7) Uani 1 1 d . . . H5 H 0.8282 1.0188 0.9047 0.063 Uiso 1 1 calc R . . C3 C 0.77428(11) 0.7990(3) 0.7347(2) 0.0561(7) Uani 1 1 d . . . H3 H 0.7446 0.7440 0.7049 0.067 Uiso 1 1 calc R . . C7 C 0.89972(10) 0.9935(3) 0.66806(17) 0.0418(6) Uani 1 1 d . . . C10 C 0.84916(10) 1.0504(3) 0.60109(19) 0.0559(8) Uani 1 1 d . . . H10A H 0.8301 0.9643 0.5672 0.084 Uiso 1 1 calc R . . H10B H 0.8545 1.1240 0.5623 0.084 Uiso 1 1 calc R . . H10C H 0.8309 1.0990 0.6314 0.084 Uiso 1 1 calc R . . C6 C 0.86320(10) 0.9558(4) 0.82653(17) 0.0513(7) Uani 1 1 d . . . H6 H 0.8936 1.0055 0.8587 0.062 Uiso 1 1 calc R . . C2 C 0.81262(11) 0.7950(3) 0.7058(2) 0.0545(7) Uani 1 1 d . . . H2 H 0.8088 0.7379 0.6558 0.065 Uiso 1 1 calc R . . C18 C 1.20580(10) 0.5629(4) 0.5422(2) 0.0572(7) Uani 1 1 d . . . H18A H 1.2201 0.5337 0.6034 0.086 Uiso 1 1 calc R . . H18B H 1.1984 0.6719 0.5372 0.086 Uiso 1 1 calc R . . H18C H 1.2294 0.5405 0.5165 0.086 Uiso 1 1 calc R . . C9 C 0.93000(12) 1.1229(4) 0.7283(2) 0.0656(8) Uani 1 1 d . . . H9A H 0.9104 1.1700 0.7566 0.098 Uiso 1 1 calc R . . H9B H 0.9382 1.1994 0.6941 0.098 Uiso 1 1 calc R . . H9C H 0.9605 1.0813 0.7724 0.098 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 S2 0.0417(4) 0.0458(4) 0.0408(4) -0.0056(3) 0.0249(3) 0.0036(3) S1 0.0425(4) 0.0506(4) 0.0377(4) 0.0129(3) 0.0244(3) 0.0150(3) Cl1 0.0634(5) 0.0769(5) 0.0789(5) 0.0207(4) 0.0527(4) 0.0202(4) N1 0.0354(11) 0.0417(12) 0.0357(11) 0.0073(9) 0.0221(9) 0.0068(9) N2 0.0380(11) 0.0382(11) 0.0338(11) 0.0025(8) 0.0218(9) 0.0037(9) O1 0.0555(11) 0.0455(10) 0.0592(11) 0.0157(8) 0.0412(10) 0.0186(8) C11 0.0306(12) 0.0343(12) 0.0314(12) -0.0006(10) 0.0165(10) -0.0005(10) C13 0.0310(12) 0.0360(12) 0.0319(12) 0.0002(10) 0.0156(10) 0.0010(10) C15 0.0343(13) 0.0388(13) 0.0350(12) -0.0036(10) 0.0186(10) 0.0009(10) C14 0.0413(14) 0.0436(14) 0.0331(12) 0.0035(10) 0.0221(11) 0.0030(11) C4 0.0492(16) 0.0485(16) 0.0504(16) 0.0139(13) 0.0323(13) 0.0144(12) O3 0.0583(12) 0.0824(14) 0.0384(10) 0.0005(9) 0.0282(9) 0.0118(10) C8 0.0407(14) 0.0442(15) 0.0434(14) 0.0086(12) 0.0234(12) 0.0084(12) C12 0.0334(12) 0.0339(12) 0.0311(12) -0.0010(9) 0.0167(10) -0.0005(10) O2 0.0747(14) 0.0657(13) 0.0701(13) 0.0320(11) 0.0522(12) 0.0304(11) O4 0.0742(14) 0.0445(11) 0.0790(14) -0.0057(10) 0.0488(12) 0.0110(9) C16 0.0439(14) 0.0433(15) 0.0426(14) 0.0058(11) 0.0215(12) 0.0120(11) C17 0.0492(16) 0.0478(15) 0.0367(13) 0.0112(11) 0.0243(12) 0.0115(12) C1 0.0458(15) 0.0428(14) 0.0479(15) 0.0104(12) 0.0309(13) 0.0159(12) C5 0.0597(18) 0.0693(19) 0.0372(14) 0.0014(13) 0.0275(13) 0.0108(15) C3 0.0592(18) 0.0504(17) 0.072(2) -0.0026(14) 0.0399(15) -0.0045(13) C7 0.0487(15) 0.0386(14) 0.0483(14) 0.0090(12) 0.0303(12) 0.0114(11) C10 0.0578(18) 0.0584(18) 0.0616(18) 0.0184(14) 0.0347(15) 0.0240(14) C6 0.0443(16) 0.073(2) 0.0386(14) 0.0034(13) 0.0186(12) 0.0029(13) C2 0.072(2) 0.0422(15) 0.0687(19) -0.0095(14) 0.0482(17) -0.0035(14) C18 0.0448(16) 0.073(2) 0.0607(18) -0.0020(15) 0.0286(14) -0.0041(14) C9 0.077(2) 0.0576(19) 0.076(2) -0.0066(16) 0.0462(18) -0.0010(16) _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 S2 O4 1.426(2) . ? S2 O3 1.4308(19) . ? S2 C18 1.749(3) . ? S2 C15 1.759(2) . ? S1 C13 1.740(2) . ? S1 C11 1.741(2) . ? Cl1 C4 1.746(3) . ? N1 C8 1.355(3) . ? N1 C11 1.383(3) . ? N1 H1 0.8600(10) . ? N2 C11 1.294(3) . ? N2 C12 1.382(3) . ? O1 C1 1.386(3) . ? O1 C7 1.444(3) . ? C13 C14 1.388(3) . ? C13 C12 1.400(3) . ? C15 C14 1.384(3) . ? C15 C16 1.397(3) . ? C14 H14 0.9300 . ? C4 C3 1.369(4) . ? C4 C5 1.370(4) . ? C8 O2 1.218(3) . ? C8 C7 1.529(3) . ? C12 C17 1.390(3) . ? C16 C17 1.370(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C1 C6 1.374(4) . ? C1 C2 1.381(4) . ? C5 C6 1.381(4) . ? C5 H5 0.9300 . ? C3 C2 1.378(4) . ? C3 H3 0.9300 . ? C7 C10 1.517(4) . ? C7 C9 1.518(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C6 H6 0.9300 . ? C2 H2 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 O4 S2 O3 119.16(12) . . ? O4 S2 C18 107.41(14) . . ? O3 S2 C18 107.91(14) . . ? O4 S2 C15 108.53(11) . . ? O3 S2 C15 108.93(11) . . ? C18 S2 C15 103.84(13) . . ? C13 S1 C11 87.83(10) . . ? C8 N1 C11 124.5(2) . . ? C8 N1 H1 118.5(18) . . ? C11 N1 H1 116.5(18) . . ? C11 N2 C12 109.73(18) . . ? C1 O1 C7 117.59(17) . . ? N2 C11 N1 119.5(2) . . ? N2 C11 S1 117.48(16) . . ? N1 C11 S1 123.06(17) . . ? C14 C13 C12 121.2(2) . . ? C14 C13 S1 129.03(18) . . ? C12 C13 S1 109.77(16) . . ? C14 C15 C16 121.9(2) . . ? C14 C15 S2 119.85(17) . . ? C16 C15 S2 118.25(18) . . ? C15 C14 C13 117.4(2) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C3 C4 C5 121.3(2) . . ? C3 C4 Cl1 118.8(2) . . ? C5 C4 Cl1 119.9(2) . . ? O2 C8 N1 122.5(2) . . ? O2 C8 C7 121.0(2) . . ? N1 C8 C7 116.3(2) . . ? N2 C12 C17 124.6(2) . . ? N2 C12 C13 115.1(2) . . ? C17 C12 C13 120.2(2) . . ? C17 C16 C15 120.3(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 119.0(2) . . ? C16 C17 H17 120.5 . . ? C12 C17 H17 120.5 . . ? C6 C1 C2 120.1(2) . . ? C6 C1 O1 121.6(2) . . ? C2 C1 O1 118.2(2) . . ? C4 C5 C6 119.4(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? O1 C7 C10 112.6(2) . . ? O1 C7 C9 109.6(2) . . ? C10 C7 C9 111.8(2) . . ? O1 C7 C8 105.60(18) . . ? C10 C7 C8 109.1(2) . . ? C9 C7 C8 107.9(2) . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 C6 C5 119.9(3) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? S2 C18 H18A 109.5 . . ? S2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C12 N2 C11 N1 179.8(2) . . . . ? C12 N2 C11 S1 -1.0(3) . . . . ? C8 N1 C11 N2 161.8(2) . . . . ? C8 N1 C11 S1 -17.3(3) . . . . ? C13 S1 C11 N2 1.98(19) . . . . ? C13 S1 C11 N1 -178.9(2) . . . . ? C11 S1 C13 C14 180.0(2) . . . . ? C11 S1 C13 C12 -2.25(18) . . . . ? O4 S2 C15 C14 -144.8(2) . . . . ? O3 S2 C15 C14 -13.7(2) . . . . ? C18 S2 C15 C14 101.1(2) . . . . ? O4 S2 C15 C16 37.4(2) . . . . ? O3 S2 C15 C16 168.57(19) . . . . ? C18 S2 C15 C16 -76.6(2) . . . . ? C16 C15 C14 C13 -1.8(4) . . . . ? S2 C15 C14 C13 -179.48(17) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? S1 C13 C14 C15 178.05(19) . . . . ? C11 N1 C8 O2 5.9(4) . . . . ? C11 N1 C8 C7 -169.9(2) . . . . ? C11 N2 C12 C17 177.7(2) . . . . ? C11 N2 C12 C13 -0.9(3) . . . . ? C14 C13 C12 N2 -179.7(2) . . . . ? S1 C13 C12 N2 2.3(3) . . . . ? C14 C13 C12 C17 1.7(4) . . . . ? S1 C13 C12 C17 -176.35(19) . . . . ? C14 C15 C16 C17 1.0(4) . . . . ? S2 C15 C16 C17 178.7(2) . . . . ? C15 C16 C17 C12 1.1(4) . . . . ? N2 C12 C17 C16 179.0(2) . . . . ? C13 C12 C17 C16 -2.4(4) . . . . ? C7 O1 C1 C6 -83.5(3) . . . . ? C7 O1 C1 C2 99.9(3) . . . . ? C3 C4 C5 C6 1.2(4) . . . . ? Cl1 C4 C5 C6 -179.4(2) . . . . ? C5 C4 C3 C2 -2.4(4) . . . . ? Cl1 C4 C3 C2 178.1(2) . . . . ? C1 O1 C7 C10 -42.2(3) . . . . ? C1 O1 C7 C9 82.9(3) . . . . ? C1 O1 C7 C8 -161.1(2) . . . . ? O2 C8 C7 O1 167.4(2) . . . . ? N1 C8 C7 O1 -16.7(3) . . . . ? O2 C8 C7 C10 46.2(3) . . . . ? N1 C8 C7 C10 -137.9(2) . . . . ? O2 C8 C7 C9 -75.5(3) . . . . ? N1 C8 C7 C9 100.4(3) . . . . ? C2 C1 C6 C5 -3.5(4) . . . . ? O1 C1 C6 C5 180.0(2) . . . . ? C4 C5 C6 C1 1.8(4) . . . . ? C4 C3 C2 C1 0.7(4) . . . . ? C6 C1 C2 C3 2.2(4) . . . . ? O1 C1 C2 C3 178.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.337 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.086 _iucr_refine_instructions_details ; TITL 2hugotm in C2/c CELL 0.71073 29.0018 8.6295 16.5593 90.000 113.948 90.000 ZERR 8.00 0.0031 0.0009 0.0018 0.000 0.002 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O S Cl UNIT 144 136 16 32 16 8 OMIT -3.00 50.00 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 CONF DFIX 0.86 0.001 N1 H1 SIZE 0.21 0.25 0.27 WGHT 0.062100 1.669500 FVAR 0.196420 TEMP 21 MOLE 1 S2 5 1.150146 0.458531 0.486483 11.000000 0.041650 0.045800 = 0.040750 -0.005600 0.024920 0.003650 S1 5 0.996410 0.788493 0.526660 11.000000 0.042520 0.050580 = 0.037680 0.012890 0.024420 0.014960 Cl1 6 0.730756 0.893991 0.841802 11.000000 0.063410 0.076900 = 0.078880 0.020750 0.052730 0.020210 N1 3 0.955967 0.796335 0.650911 11.000000 0.035430 0.041690 = 0.035740 0.007340 0.022060 0.006820 H1 2 0.953350 0.753202 0.695679 11.000000 -1.500000 N2 3 1.022930 0.631580 0.673038 11.000000 0.038020 0.038180 = 0.033770 0.002450 0.021850 0.003680 O1 4 0.894763 0.866364 0.720707 11.000000 0.055520 0.045530 = 0.059220 0.015690 0.041150 0.018630 C11 1 0.991352 0.733965 0.623982 11.000000 0.030640 0.034270 = 0.031380 -0.000650 0.016500 -0.000500 C13 1 1.045177 0.654749 0.552107 11.000000 0.031020 0.036050 = 0.031950 0.000220 0.015610 0.000980 C15 1 1.111861 0.509436 0.541851 11.000000 0.034350 0.038770 = 0.034960 -0.003580 0.018650 0.000920 C14 1 1.073939 0.618117 0.505157 11.000000 0.041340 0.043600 = 0.033120 0.003530 0.022110 0.002960 AFIX 43 H14 2 1.067968 0.664744 0.451189 11.000000 -1.200000 AFIX 0 C4 1 0.780335 0.885094 0.807768 11.000000 0.049160 0.048490 = 0.050370 0.013940 0.032320 0.014420 O3 4 1.127394 0.515269 0.397746 11.000000 0.058260 0.082430 = 0.038440 0.000530 0.028190 0.011760 C8 1 0.930394 0.929707 0.619069 11.000000 0.040670 0.044190 = 0.043430 0.008570 0.023420 0.008400 C12 1 1.054518 0.585124 0.633664 11.000000 0.033420 0.033870 = 0.031110 -0.000950 0.016730 -0.000450 O2 4 0.933630 1.000992 0.558125 11.000000 0.074680 0.065680 = 0.070050 0.031950 0.052240 0.030380 O4 4 1.162296 0.297940 0.501238 11.000000 0.074200 0.044530 = 0.078990 -0.005730 0.048810 0.011010 C16 1 1.122116 0.441788 0.623978 11.000000 0.043930 0.043310 = 0.042560 0.005790 0.021540 0.012020 AFIX 43 H16 2 1.148210 0.370328 0.647317 11.000000 -1.200000 AFIX 0 C17 1 1.093932 0.480173 0.670314 11.000000 0.049250 0.047830 = 0.036730 0.011180 0.024350 0.011540 AFIX 43 H17 2 1.101059 0.436665 0.725479 11.000000 -1.200000 AFIX 0 C1 1 0.856770 0.875682 0.751016 11.000000 0.045750 0.042770 = 0.047860 0.010420 0.030870 0.015910 C5 1 0.824416 0.962419 0.854551 11.000000 0.059680 0.069350 = 0.037150 0.001400 0.027520 0.010760 AFIX 43 H5 2 0.828196 1.018835 0.904706 11.000000 -1.200000 AFIX 0 C3 1 0.774276 0.799049 0.734678 11.000000 0.059180 0.050420 = 0.071730 -0.002640 0.039920 -0.004550 AFIX 43 H3 2 0.744614 0.743972 0.704863 11.000000 -1.200000 AFIX 0 C7 1 0.899720 0.993457 0.668059 11.000000 0.048710 0.038600 = 0.048330 0.009000 0.030280 0.011430 C10 1 0.849164 1.050408 0.601087 11.000000 0.057810 0.058420 = 0.061620 0.018360 0.034730 0.024010 AFIX 137 H10A 2 0.830065 0.964258 0.567242 11.000000 -1.500000 H10B 2 0.854498 1.124047 0.562272 11.000000 -1.500000 H10C 2 0.830935 1.098961 0.631365 11.000000 -1.500000 AFIX 0 C6 1 0.863198 0.955811 0.826533 11.000000 0.044350 0.072670 = 0.038560 0.003360 0.018600 0.002920 AFIX 43 H6 2 0.893619 1.005528 0.858736 11.000000 -1.200000 AFIX 0 C2 1 0.812618 0.794971 0.705788 11.000000 0.071760 0.042200 = 0.068650 -0.009510 0.048150 -0.003540 AFIX 43 H2 2 0.808764 0.737856 0.655824 11.000000 -1.200000 AFIX 0 C18 1 1.205795 0.562938 0.542180 11.000000 0.044760 0.073010 = 0.060740 -0.002000 0.028610 -0.004080 AFIX 137 H18A 2 1.220145 0.533738 0.603390 11.000000 -1.500000 H18B 2 1.198418 0.671851 0.537222 11.000000 -1.500000 H18C 2 1.229369 0.540535 0.516503 11.000000 -1.500000 AFIX 0 C9 1 0.929997 1.122945 0.728317 11.000000 0.077470 0.057640 = 0.076340 -0.006630 0.046210 -0.000980 AFIX 137 H9A 2 0.910434 1.170018 0.756583 11.000000 -1.500000 H9B 2 0.938163 1.199399 0.694089 11.000000 -1.500000 H9C 2 0.960543 1.081314 0.772388 11.000000 -1.500000 AFIX 0 Q1 1 0.732300 0.800200 0.819800 11.000000 0.050000 0.34 Q2 1 1.126400 0.479100 0.512600 11.000000 0.050000 0.31 Q3 1 0.760000 0.932200 0.888100 11.000000 0.050000 0.30 Q4 1 0.803600 0.880200 0.832400 11.000000 0.050000 0.30 Q5 1 0.756400 0.895000 0.822400 11.000000 0.050000 0.29 HKLF 4 END ;