# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author 'Thorfinnur Gunnlaugsson' _publ_contact_author_email gunnlaut@tcd.ie _publ_contact_author_name 'Thorfinnur Gunnlaugsson' loop_ _publ_author_name 'Thorfinnur Gunnlaugsson' 'Paul E. Kruger' 'Haslin Dato Paduka Ali' T.McCabe 'Susan Quinn' # Attachment 'Compound_2_revised.cif' data_la113am _database_code_depnum_ccdc_archive 'CCDC 605750' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bis-((R),(S)-napthalenylethyl)thiourea _chemical_melting_point 454 _chemical_formula_moiety ? _chemical_formula_sum 'C54 H48 N4 O2 S4' _chemical_formula_weight 913.20 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 22.838(3) _cell_length_b 10.8673(14) _cell_length_c 10.1015(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2507.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 396(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.805022 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9651 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2240 _reflns_number_gt 2214 _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^)+(0.0581P)^2^+0.4947P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_number_reflns 2240 _refine_ls_number_parameters 161 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.080 _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 N1 N 0.54952(5) 0.66202(11) 1.07103(14) 0.0306(3) Uani 1 1 d . . . H1 H 0.5465 0.5971 1.0228 0.037 Uiso 1 1 calc R . . C3 C 0.61796(7) 0.85268(14) 0.87438(19) 0.0391(4) Uani 1 1 d . . . H3 H 0.5916 0.8738 0.9408 0.047 Uiso 1 1 calc R . . C5 C 0.65146(6) 0.66895(14) 1.00359(16) 0.0302(3) Uani 1 1 d . . . C4 C 0.65405(6) 0.74686(14) 0.88979(16) 0.0322(3) Uani 1 1 d . . . C8 C 0.73188(7) 0.61605(16) 0.80076(17) 0.0396(4) Uani 1 1 d . . . H8 H 0.7592 0.5987 0.7351 0.047 Uiso 1 1 calc R . . C13 C 0.62246(8) 0.6412(2) 1.24768(19) 0.0508(5) Uani 1 1 d . . . H13A H 0.5947 0.6690 1.3124 0.076 Uiso 1 1 calc R . . H13B H 0.6612 0.6653 1.2741 0.076 Uiso 1 1 calc R . . H13C H 0.6206 0.5532 1.2408 0.076 Uiso 1 1 calc R . . C9 C 0.69452(6) 0.71869(15) 0.78712(16) 0.0371(4) Uani 1 1 d . . . C6 C 0.68729(6) 0.56855(14) 1.01017(17) 0.0349(3) Uani 1 1 d . . . H6 H 0.6847 0.5162 1.0827 0.042 Uiso 1 1 calc R . . C1 C 0.66046(8) 0.89303(19) 0.6610(2) 0.0563(5) Uani 1 1 d . . . H1A H 0.6619 0.9410 0.5848 0.068 Uiso 1 1 calc R . . C11 C 0.60812(7) 0.69859(14) 1.11390(15) 0.0327(4) Uani 1 1 d . . . H11 H 0.6079 0.7881 1.1255 0.039 Uiso 1 1 calc R . . C10 C 0.69628(7) 0.79295(17) 0.6728(2) 0.0484(4) Uani 1 1 d . . . H10 H 0.7221 0.7736 0.6047 0.058 Uiso 1 1 calc R . . S1 S 0.5000 0.86505(5) 1.16780(7) 0.0365(2) Uani 0.948(4) 2 d SP . . C12 C 0.5000 0.72243(18) 1.10148(19) 0.0278(4) Uani 1 2 d S . . C7 C 0.72828(6) 0.54245(15) 0.90893(18) 0.0404(4) Uani 1 1 d . . . H7 H 0.7529 0.4746 0.9166 0.048 Uiso 1 1 calc R . . C2 C 0.62165(8) 0.92369(17) 0.7626(2) 0.0505(5) Uani 1 1 d . . . H2 H 0.5981 0.9930 0.7543 0.061 Uiso 1 1 calc R . . S2 S 0.97238(4) 0.82777(8) 0.08376(9) 0.0361(3) Uani 0.455(3) 1 d P . . O1 O 1.0000 0.92708(14) -0.00505(17) 0.0411(6) Uani 0.978(7) 2 d SP . . C15 C 1.0000 0.8479(3) 0.2407(3) 0.0672(9) Uani 1 2 d S . . C14 C 1.0000 0.6891(3) 0.0351(3) 0.0782(11) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0251(6) 0.0282(6) 0.0384(7) -0.0014(5) -0.0010(5) -0.0003(5) C3 0.0293(7) 0.0350(9) 0.0528(10) 0.0045(7) -0.0027(7) -0.0022(6) C5 0.0223(7) 0.0321(7) 0.0361(7) -0.0012(6) -0.0049(6) -0.0028(5) C4 0.0233(6) 0.0336(7) 0.0398(8) 0.0003(7) -0.0042(6) -0.0069(6) C8 0.0290(8) 0.0447(9) 0.0449(9) -0.0141(7) 0.0004(7) -0.0044(6) C13 0.0387(10) 0.0770(14) 0.0368(9) 0.0064(8) -0.0022(8) 0.0082(8) C9 0.0263(7) 0.0411(8) 0.0438(9) -0.0050(7) -0.0016(7) -0.0103(6) C6 0.0308(7) 0.0346(8) 0.0394(8) -0.0003(6) -0.0077(7) -0.0002(6) C1 0.0498(10) 0.0614(11) 0.0578(11) 0.0248(11) -0.0031(11) -0.0154(9) C11 0.0264(7) 0.0350(8) 0.0366(8) -0.0021(6) -0.0039(6) -0.0008(6) C10 0.0399(9) 0.0591(10) 0.0463(9) 0.0059(10) 0.0043(8) -0.0161(8) S1 0.0297(3) 0.0258(3) 0.0540(4) -0.0066(2) 0.000 0.000 C12 0.0283(10) 0.0274(10) 0.0277(10) 0.0042(8) 0.000 0.000 C7 0.0304(7) 0.0397(8) 0.0511(10) -0.0131(8) -0.0083(7) 0.0069(6) C2 0.0396(9) 0.0420(9) 0.0699(12) 0.0204(9) -0.0062(9) -0.0056(7) S2 0.0388(5) 0.0329(5) 0.0367(5) 0.0058(4) -0.0051(4) -0.0047(4) O1 0.0603(11) 0.0276(9) 0.0355(9) 0.0025(7) 0.000 0.000 C15 0.102(3) 0.0673(19) 0.0319(14) 0.0028(12) 0.000 0.000 C14 0.151(4) 0.0284(13) 0.0557(18) -0.0005(12) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C12 1.3433(16) . ? N1 C11 1.4618(19) . ? C3 C2 1.370(3) . ? C3 C4 1.423(2) . ? C5 C6 1.365(2) . ? C5 C4 1.429(2) . ? C5 C11 1.525(2) . ? C4 C9 1.423(2) . ? C8 C7 1.357(3) . ? C8 C9 1.411(3) . ? C13 C11 1.524(2) . ? C9 C10 1.409(3) . ? C6 C7 1.415(2) . ? C1 C10 1.366(3) . ? C1 C2 1.397(3) . ? S1 C12 1.689(2) . ? C12 N1 1.3433(17) 4_655 ? S2 S2 1.2616(19) 4_755 ? S2 O1 1.5386(17) . ? S2 C14 1.706(3) . ? S2 C15 1.720(3) . ? O1 S2 1.5387(17) 4_755 ? C15 S2 1.720(3) 4_755 ? C14 S2 1.706(3) 4_755 ? 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 C12 N1 C11 124.76(13) . . ? C2 C3 C4 120.63(17) . . ? C6 C5 C4 119.20(15) . . ? C6 C5 C11 121.48(15) . . ? C4 C5 C11 119.31(13) . . ? C9 C4 C3 118.06(15) . . ? C9 C4 C5 119.07(14) . . ? C3 C4 C5 122.87(15) . . ? C7 C8 C9 120.54(15) . . ? C10 C9 C8 121.02(15) . . ? C10 C9 C4 119.52(15) . . ? C8 C9 C4 119.46(15) . . ? C5 C6 C7 121.43(16) . . ? C10 C1 C2 120.37(18) . . ? N1 C11 C13 110.38(14) . . ? N1 C11 C5 108.69(12) . . ? C13 C11 C5 114.97(13) . . ? C1 C10 C9 120.70(18) . . ? N1 C12 N1 114.68(18) . 4_655 ? N1 C12 S1 122.64(9) . . ? N1 C12 S1 122.65(9) 4_655 . ? C8 C7 C6 120.26(15) . . ? C3 C2 C1 120.70(18) . . ? S2 S2 O1 65.80(4) 4_755 . ? S2 S2 C14 68.30(5) 4_755 . ? O1 S2 C14 107.45(12) . . ? S2 S2 C15 68.48(5) 4_755 . ? O1 S2 C15 107.33(12) . . ? C14 S2 C15 104.03(16) . . ? S2 O1 S2 48.41(9) . 4_755 ? S2 C15 S2 43.03(10) 4_755 . ? S2 C14 S2 43.39(9) 4_755 . ? 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 C2 C3 C4 C9 1.1(2) . . . . ? C2 C3 C4 C5 -179.25(15) . . . . ? C6 C5 C4 C9 -0.9(2) . . . . ? C11 C5 C4 C9 -179.93(12) . . . . ? C6 C5 C4 C3 179.46(14) . . . . ? C11 C5 C4 C3 0.4(2) . . . . ? C7 C8 C9 C10 -177.48(15) . . . . ? C7 C8 C9 C4 1.9(2) . . . . ? C3 C4 C9 C10 -2.1(2) . . . . ? C5 C4 C9 C10 178.24(14) . . . . ? C3 C4 C9 C8 178.54(14) . . . . ? C5 C4 C9 C8 -1.1(2) . . . . ? C4 C5 C6 C7 2.2(2) . . . . ? C11 C5 C6 C7 -178.77(14) . . . . ? C12 N1 C11 C13 88.46(19) . . . . ? C12 N1 C11 C5 -144.60(16) . . . . ? C6 C5 C11 N1 -102.77(15) . . . . ? C4 C5 C11 N1 76.26(16) . . . . ? C6 C5 C11 C13 21.5(2) . . . . ? C4 C5 C11 C13 -159.48(15) . . . . ? C2 C1 C10 C9 0.3(3) . . . . ? C8 C9 C10 C1 -179.23(16) . . . . ? C4 C9 C10 C1 1.4(2) . . . . ? C11 N1 C12 N1 -169.27(11) . . . 4_655 ? C11 N1 C12 S1 12.8(2) . . . . ? C9 C8 C7 C6 -0.6(2) . . . . ? C5 C6 C7 C8 -1.5(2) . . . . ? C4 C3 C2 C1 0.6(3) . . . . ? C10 C1 C2 C3 -1.4(3) . . . . ? C14 S2 O1 S2 -55.52(10) . . . 4_755 ? C15 S2 O1 S2 55.85(11) . . . 4_755 ? O1 S2 C15 S2 -54.23(11) . . . 4_755 ? C14 S2 C15 S2 59.46(10) . . . 4_755 ? O1 S2 C14 S2 54.02(10) . . . 4_755 ? C15 S2 C14 S2 -59.58(10) . . . 4_755 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.326 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.042 # Attachment 'Compound_3_revised.cif' data_la114am _database_code_depnum_ccdc_archive 'CCDC 605751' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bis-((S)-napthalenylethyl)thiourea _chemical_melting_point 383 _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 N2 O S2' _chemical_formula_weight 462.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 17.0684(15) _cell_length_b 8.0774(7) _cell_length_c 18.8459(17) _cell_angle_alpha 90.00 _cell_angle_beta 109.117(2) _cell_angle_gamma 90.00 _cell_volume 2455.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 396(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.810283 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9728 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _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 1.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4269 _reflns_number_gt 3837 _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^+1.0574P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration ad loop_ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(7) _refine_ls_number_reflns 4269 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.20288(5) 0.23422(9) 0.17401(4) 0.03668(19) Uani 1 1 d . . . S2 S 0.94813(4) 0.84147(10) 0.26802(4) 0.03807(19) Uani 1 1 d . . . N2 N 0.12824(13) -0.0331(3) 0.20195(11) 0.0270(5) Uani 1 1 d . . . H6 H 0.1119 -0.0893 0.2333 0.032 Uiso 1 1 calc R . . O1 O 1.03606(12) 0.8961(3) 0.30566(11) 0.0396(5) Uani 1 1 d . . . C19 C -0.02534(16) -0.1664(4) 0.08921(13) 0.0271(5) Uani 1 1 d . . . N1 N 0.12597(14) 0.1876(3) 0.27484(13) 0.0327(5) Uani 1 1 d . . . H5 H 0.0980 0.1243 0.2944 0.039 Uiso 1 1 calc R . . C14 C 0.05614(17) -0.2342(3) 0.11152(14) 0.0288(6) Uani 1 1 d . . . C10 C 0.22120(15) 0.3628(3) 0.37318(14) 0.0280(6) Uani 1 1 d . . . C5 C 0.26586(16) 0.5153(4) 0.39105(15) 0.0291(6) Uani 1 1 d . . . C21 C -0.12049(19) 0.0646(4) 0.05976(17) 0.0402(7) Uani 1 1 d . . . H21 H -0.1300 0.1775 0.0514 0.048 Uiso 1 1 calc R . . C4 C 0.24433(19) 0.6597(4) 0.34828(16) 0.0342(6) Uani 1 1 d . . . H4 H 0.1970 0.6595 0.3061 0.041 Uiso 1 1 calc R . . C8 C 0.31598(18) 0.2390(5) 0.48456(16) 0.0419(7) Uani 1 1 d . . . H8 H 0.3313 0.1469 0.5157 0.050 Uiso 1 1 calc R . . C18 C -0.09387(17) -0.2749(4) 0.07887(14) 0.0324(6) Uani 1 1 d . . . C12 C 0.14987(15) 0.1253(3) 0.21950(14) 0.0270(6) Uani 1 1 d . . . C23 C -0.17420(19) -0.2064(4) 0.06151(15) 0.0379(7) Uani 1 1 d . . . H23 H -0.2190 -0.2766 0.0559 0.045 Uiso 1 1 calc R . . C9 C 0.24690(17) 0.2295(4) 0.41882(16) 0.0360(6) Uani 1 1 d . . . H9 H 0.2182 0.1300 0.4063 0.043 Uiso 1 1 calc R . . C20 C -0.04202(18) 0.0051(4) 0.07845(15) 0.0314(6) Uani 1 1 d . . . H20 H 0.0017 0.0784 0.0843 0.038 Uiso 1 1 calc R . . C6 C 0.33765(17) 0.5204(4) 0.45677(16) 0.0361(7) Uani 1 1 d . . . C7 C 0.36019(18) 0.3795(4) 0.50307(15) 0.0421(8) Uani 1 1 d . . . H7 H 0.4059 0.3837 0.5467 0.051 Uiso 1 1 calc R . . C26 C 0.06876(18) 0.4208(4) 0.32229(19) 0.0436(8) Uani 1 1 d . . . H26A H 0.0213 0.4214 0.2775 0.065 Uiso 1 1 calc R . . H26B H 0.0801 0.5316 0.3414 0.065 Uiso 1 1 calc R . . H26C H 0.0577 0.3516 0.3594 0.065 Uiso 1 1 calc R . . C15 C 0.0657(2) -0.4012(4) 0.11722(17) 0.0411(7) Uani 1 1 d . . . H15 H 0.1186 -0.4462 0.1299 0.049 Uiso 1 1 calc R . . C11 C 0.14373(16) 0.3538(4) 0.30428(15) 0.0313(6) Uani 1 1 d . . . H11 H 0.1526 0.4237 0.2651 0.038 Uiso 1 1 calc R . . C13 C 0.13009(16) -0.1182(3) 0.13399(14) 0.0289(6) Uani 1 1 d . . . H13 H 0.1213 -0.0350 0.0943 0.035 Uiso 1 1 calc R . . C3 C 0.38355(19) 0.6689(4) 0.47368(18) 0.0441(8) Uani 1 1 d . . . H3 H 0.4305 0.6731 0.5162 0.053 Uiso 1 1 calc R . . C25 C 0.91644(19) 0.7436(4) 0.33829(19) 0.0479(8) Uani 1 1 d . . . H25A H 0.9470 0.6426 0.3535 0.072 Uiso 1 1 calc R . . H25B H 0.8582 0.7192 0.3186 0.072 Uiso 1 1 calc R . . H25C H 0.9269 0.8159 0.3808 0.072 Uiso 1 1 calc R . . C2 C 0.3618(2) 0.8048(5) 0.43037(19) 0.0518(9) Uani 1 1 d . . . H2 H 0.3937 0.9003 0.4427 0.062 Uiso 1 1 calc R . . C16 C -0.0032(2) -0.5076(4) 0.10419(19) 0.0515(9) Uani 1 1 d . . . H16 H 0.0049 -0.6215 0.1076 0.062 Uiso 1 1 calc R . . C22 C -0.18751(19) -0.0421(4) 0.05290(17) 0.0405(7) Uani 1 1 d . . . H22 H -0.2407 0.0004 0.0425 0.049 Uiso 1 1 calc R . . C1 C 0.2905(2) 0.8015(4) 0.36631(18) 0.0464(8) Uani 1 1 d . . . H1 H 0.2747 0.8952 0.3364 0.056 Uiso 1 1 calc R . . C17 C -0.0802(2) -0.4466(4) 0.08698(18) 0.0457(8) Uani 1 1 d . . . H17 H -0.1247 -0.5181 0.0804 0.055 Uiso 1 1 calc R . . C27 C 0.21347(18) -0.1986(4) 0.14557(17) 0.0393(7) Uani 1 1 d . . . H27A H 0.2563 -0.1163 0.1610 0.059 Uiso 1 1 calc R . . H27B H 0.2138 -0.2483 0.0994 0.059 Uiso 1 1 calc R . . H27C H 0.2232 -0.2822 0.1837 0.059 Uiso 1 1 calc R . . C24 C 0.8869(2) 1.0239(5) 0.2595(2) 0.0542(9) Uani 1 1 d . . . H24A H 0.9021 1.0799 0.3070 0.081 Uiso 1 1 calc R . . H24B H 0.8293 0.9943 0.2443 0.081 Uiso 1 1 calc R . . H24C H 0.8964 1.0959 0.2225 0.081 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 0.0374(4) 0.0324(4) 0.0465(4) 0.0014(3) 0.0221(3) -0.0039(3) S2 0.0346(4) 0.0464(5) 0.0370(4) -0.0059(3) 0.0169(3) -0.0035(4) N2 0.0306(12) 0.0263(13) 0.0275(11) 0.0009(9) 0.0143(9) 0.0001(10) O1 0.0306(11) 0.0514(14) 0.0396(11) 0.0077(10) 0.0152(8) -0.0023(9) C19 0.0353(14) 0.0249(14) 0.0219(11) 0.0009(11) 0.0103(10) 0.0026(12) N1 0.0387(14) 0.0279(13) 0.0385(13) -0.0024(10) 0.0221(11) -0.0072(10) C14 0.0359(15) 0.0247(15) 0.0264(13) -0.0006(11) 0.0109(11) 0.0017(12) C10 0.0288(14) 0.0294(15) 0.0312(13) -0.0007(12) 0.0174(10) 0.0053(12) C5 0.0291(14) 0.0342(15) 0.0288(14) -0.0035(12) 0.0162(12) 0.0052(13) C21 0.0409(18) 0.0266(16) 0.0486(18) -0.0047(13) 0.0084(14) 0.0084(13) C4 0.0380(16) 0.0288(15) 0.0372(15) -0.0035(13) 0.0144(13) 0.0015(13) C8 0.0403(17) 0.052(2) 0.0380(16) 0.0158(16) 0.0184(13) 0.0167(17) C18 0.0386(16) 0.0326(15) 0.0245(13) -0.0034(12) 0.0082(11) -0.0068(14) C12 0.0199(13) 0.0308(15) 0.0291(13) 0.0008(11) 0.0063(10) 0.0045(11) C23 0.0357(16) 0.0453(19) 0.0316(15) -0.0080(13) 0.0097(12) -0.0111(13) C9 0.0394(16) 0.0347(15) 0.0413(15) 0.0047(14) 0.0233(13) 0.0052(14) C20 0.0345(16) 0.0245(15) 0.0348(15) -0.0037(12) 0.0106(12) 0.0002(12) C6 0.0286(15) 0.0474(18) 0.0362(16) -0.0110(14) 0.0161(13) 0.0048(14) C7 0.0296(15) 0.065(2) 0.0311(15) 0.0008(15) 0.0092(11) 0.0128(15) C26 0.0315(16) 0.0439(18) 0.0553(19) -0.0098(15) 0.0139(14) 0.0026(14) C15 0.0462(19) 0.0288(16) 0.0440(17) 0.0036(14) 0.0090(14) 0.0123(15) C11 0.0342(14) 0.0256(14) 0.0370(14) -0.0027(12) 0.0158(11) 0.0028(13) C13 0.0353(15) 0.0256(15) 0.0284(13) 0.0043(11) 0.0140(11) 0.0076(12) C3 0.0313(17) 0.060(2) 0.0421(17) -0.0193(17) 0.0132(14) -0.0012(15) C25 0.0412(17) 0.0435(18) 0.068(2) 0.0111(18) 0.0301(15) 0.0019(16) C2 0.051(2) 0.044(2) 0.066(2) -0.0222(19) 0.0267(17) -0.0126(17) C16 0.060(2) 0.0205(17) 0.063(2) 0.0047(15) 0.0056(17) 0.0026(15) C22 0.0301(16) 0.0464(19) 0.0423(16) -0.0132(15) 0.0081(13) 0.0028(14) C1 0.0510(19) 0.0371(19) 0.0561(19) -0.0067(15) 0.0243(16) -0.0023(15) C17 0.053(2) 0.0306(17) 0.0461(19) 0.0025(14) 0.0057(16) -0.0096(15) C27 0.0370(16) 0.0430(18) 0.0424(16) -0.0006(14) 0.0190(13) 0.0097(13) C24 0.0355(18) 0.058(2) 0.069(2) 0.0161(19) 0.0163(16) 0.0103(17) _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 C12 1.684(3) . ? S2 O1 1.501(2) . ? S2 C25 1.772(3) . ? S2 C24 1.783(4) . ? N2 C12 1.343(3) . ? N2 C13 1.463(3) . ? C19 C20 1.415(4) . ? C19 C18 1.423(4) . ? C19 C14 1.424(4) . ? N1 C12 1.337(3) . ? N1 C11 1.446(4) . ? C14 C15 1.359(4) . ? C14 C13 1.517(4) . ? C10 C9 1.358(4) . ? C10 C5 1.430(4) . ? C10 C11 1.522(4) . ? C5 C4 1.397(4) . ? C5 C6 1.429(4) . ? C21 C20 1.356(4) . ? C21 C22 1.404(4) . ? C4 C1 1.368(4) . ? C8 C7 1.344(5) . ? C8 C9 1.405(4) . ? C18 C17 1.407(5) . ? C18 C23 1.414(4) . ? C23 C22 1.348(5) . ? C6 C7 1.409(5) . ? C6 C3 1.411(5) . ? C26 C11 1.527(4) . ? C15 C16 1.412(5) . ? C13 C27 1.514(4) . ? C3 C2 1.345(5) . ? C2 C1 1.406(5) . ? C16 C17 1.339(5) . ? 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 S2 C25 106.30(14) . . ? O1 S2 C24 105.38(15) . . ? C25 S2 C24 97.09(17) . . ? C12 N2 C13 125.5(2) . . ? C20 C19 C18 117.7(3) . . ? C20 C19 C14 123.4(3) . . ? C18 C19 C14 118.9(3) . . ? C12 N1 C11 124.7(2) . . ? C15 C14 C19 119.0(3) . . ? C15 C14 C13 121.6(3) . . ? C19 C14 C13 119.2(2) . . ? C9 C10 C5 119.8(2) . . ? C9 C10 C11 120.8(3) . . ? C5 C10 C11 119.3(2) . . ? C4 C5 C6 117.7(3) . . ? C4 C5 C10 124.4(2) . . ? C6 C5 C10 118.0(3) . . ? C20 C21 C22 120.8(3) . . ? C1 C4 C5 122.3(3) . . ? C7 C8 C9 120.8(3) . . ? C17 C18 C23 121.7(3) . . ? C17 C18 C19 119.5(3) . . ? C23 C18 C19 118.8(3) . . ? N1 C12 N2 114.9(2) . . ? N1 C12 S1 123.5(2) . . ? N2 C12 S1 121.5(2) . . ? C22 C23 C18 121.7(3) . . ? C10 C9 C8 121.2(3) . . ? C21 C20 C19 121.3(3) . . ? C7 C6 C3 121.9(3) . . ? C7 C6 C5 119.7(3) . . ? C3 C6 C5 118.4(3) . . ? C8 C7 C6 120.4(3) . . ? C14 C15 C16 121.3(3) . . ? N1 C11 C10 112.7(2) . . ? N1 C11 C26 109.2(2) . . ? C10 C11 C26 110.5(2) . . ? N2 C13 C27 111.3(2) . . ? N2 C13 C14 106.3(2) . . ? C27 C13 C14 115.6(2) . . ? C2 C3 C6 122.3(3) . . ? C3 C2 C1 119.7(3) . . ? C17 C16 C15 120.9(3) . . ? C23 C22 C21 119.6(3) . . ? C4 C1 C2 119.7(3) . . ? C16 C17 C18 120.2(3) . . ? 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 C20 C19 C14 C15 -177.1(3) . . . . ? C18 C19 C14 C15 4.5(4) . . . . ? C20 C19 C14 C13 7.5(3) . . . . ? C18 C19 C14 C13 -170.9(2) . . . . ? C9 C10 C5 C4 -179.5(3) . . . . ? C11 C10 C5 C4 -1.3(4) . . . . ? C9 C10 C5 C6 0.9(4) . . . . ? C11 C10 C5 C6 179.1(2) . . . . ? C6 C5 C4 C1 1.7(4) . . . . ? C10 C5 C4 C1 -177.9(3) . . . . ? C20 C19 C18 C17 178.2(3) . . . . ? C14 C19 C18 C17 -3.3(4) . . . . ? C20 C19 C18 C23 -2.5(4) . . . . ? C14 C19 C18 C23 175.9(2) . . . . ? C11 N1 C12 N2 178.6(2) . . . . ? C11 N1 C12 S1 -1.6(4) . . . . ? C13 N2 C12 N1 165.5(2) . . . . ? C13 N2 C12 S1 -14.3(3) . . . . ? C17 C18 C23 C22 -179.2(3) . . . . ? C19 C18 C23 C22 1.5(4) . . . . ? C5 C10 C9 C8 1.3(4) . . . . ? C11 C10 C9 C8 -176.8(2) . . . . ? C7 C8 C9 C10 -1.9(4) . . . . ? C22 C21 C20 C19 2.1(4) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? C14 C19 C20 C21 -177.6(3) . . . . ? C4 C5 C6 C7 177.9(3) . . . . ? C10 C5 C6 C7 -2.5(4) . . . . ? C4 C5 C6 C3 -1.5(4) . . . . ? C10 C5 C6 C3 178.2(2) . . . . ? C9 C8 C7 C6 0.3(4) . . . . ? C3 C6 C7 C8 -178.7(3) . . . . ? C5 C6 C7 C8 2.0(4) . . . . ? C19 C14 C15 C16 -2.4(4) . . . . ? C13 C14 C15 C16 172.9(3) . . . . ? C12 N1 C11 C10 -94.7(3) . . . . ? C12 N1 C11 C26 142.1(3) . . . . ? C9 C10 C11 N1 -26.7(3) . . . . ? C5 C10 C11 N1 155.1(2) . . . . ? C9 C10 C11 C26 95.8(3) . . . . ? C5 C10 C11 C26 -82.3(3) . . . . ? C12 N2 C13 C27 89.4(3) . . . . ? C12 N2 C13 C14 -143.9(2) . . . . ? C15 C14 C13 N2 -110.5(3) . . . . ? C19 C14 C13 N2 64.7(3) . . . . ? C15 C14 C13 C27 13.6(4) . . . . ? C19 C14 C13 C27 -171.2(2) . . . . ? C7 C6 C3 C2 -179.0(3) . . . . ? C5 C6 C3 C2 0.3(4) . . . . ? C6 C3 C2 C1 0.8(5) . . . . ? C14 C15 C16 C17 -1.1(5) . . . . ? C18 C23 C22 C21 1.3(5) . . . . ? C20 C21 C22 C23 -3.1(5) . . . . ? C5 C4 C1 C2 -0.7(5) . . . . ? C3 C2 C1 C4 -0.6(5) . . . . ? C15 C16 C17 C18 2.4(5) . . . . ? C23 C18 C17 C16 -179.3(3) . . . . ? C19 C18 C17 C16 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.563 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.047 data_la1121m _database_code_depnum_ccdc_archive 'CCDC 605752' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Bis-((R)-naphthalenylethyl)thiourea _chemical_melting_point 383 _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 N2 O S2' _chemical_formula_weight 462.65 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 17.080(2) _cell_length_b 8.1010(9) _cell_length_c 18.903(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.013(2) _cell_angle_gamma 90.00 _cell_volume 2472.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 396(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.855529 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 396(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9886 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4190 _reflns_number_gt 3555 _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 Smelxtl' _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^)+(0.0481P)^2^+1.0359P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration ad loop_ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(9) _refine_ls_number_reflns 4190 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 S1 S 0.79690(6) 0.11105(12) 0.82598(5) 0.0398(2) Uani 1 1 d . . . C10 C 0.77865(19) -0.0170(4) 0.62675(18) 0.0298(8) Uani 1 1 d . . . N1 N 0.87357(17) 0.1578(3) 0.72502(16) 0.0353(7) Uani 1 1 d . . . H9 H 0.9011 0.2215 0.7054 0.042 Uiso 1 1 calc R . . C21 C 1.0246(2) 0.5116(5) 0.91027(17) 0.0295(7) Uani 1 1 d . . . C12 C 0.84994(18) 0.2190(4) 0.78085(18) 0.0280(8) Uani 1 1 d . . . C16 C 0.9433(2) 0.5797(4) 0.88820(18) 0.0307(8) Uani 1 1 d . . . C4 C 0.7341(2) -0.1704(5) 0.60903(18) 0.0306(8) Uani 1 1 d . . . N2 N 0.87129(16) 0.3783(3) 0.79785(15) 0.0284(7) Uani 1 1 d . . . H10 H 0.8874 0.4341 0.7664 0.034 Uiso 1 1 calc R . . C3 C 0.7552(2) -0.3137(5) 0.6511(2) 0.0374(9) Uani 1 1 d . . . H3 H 0.8025 -0.3133 0.6931 0.045 Uiso 1 1 calc R . . C25 C 1.1743(2) 0.5513(5) 0.93864(19) 0.0412(10) Uani 1 1 d . . . H15 H 1.2191 0.6212 0.9442 0.049 Uiso 1 1 calc R . . C8 C 0.6841(2) 0.1064(6) 0.5157(2) 0.0436(9) Uani 1 1 d . . . H6 H 0.6689 0.1984 0.4848 0.052 Uiso 1 1 calc R . . C6 C 0.6164(2) -0.3239(6) 0.5264(2) 0.0475(11) Uani 1 1 d . . . H4 H 0.5698 -0.3283 0.4838 0.057 Uiso 1 1 calc R . . C5 C 0.6621(2) -0.1765(5) 0.5433(2) 0.0400(9) Uani 1 1 d . . . C9 C 0.7528(2) 0.1151(5) 0.5813(2) 0.0376(8) Uani 1 1 d . . . H7 H 0.7814 0.2144 0.5939 0.045 Uiso 1 1 calc R . . C23 C 1.1200(2) 0.2809(5) 0.9404(2) 0.0426(10) Uani 1 1 d . . . H13 H 1.1294 0.1684 0.9488 0.051 Uiso 1 1 calc R . . C7 C 0.6400(2) -0.0338(6) 0.4972(2) 0.0453(11) Uani 1 1 d . . . H5 H 0.5945 -0.0375 0.4537 0.054 Uiso 1 1 calc R . . C13 C 0.9313(2) -0.0743(5) 0.6775(2) 0.0467(10) Uani 1 1 d . . . H13A H 0.9418 -0.0058 0.6402 0.070 Uiso 1 1 calc R . . H13B H 0.9205 -0.1853 0.6590 0.070 Uiso 1 1 calc R . . H13C H 0.9787 -0.0735 0.7221 0.070 Uiso 1 1 calc R . . C20 C 1.0935(2) 0.6194(5) 0.92119(18) 0.0347(8) Uani 1 1 d . . . C22 C 1.0416(2) 0.3399(5) 0.92170(19) 0.0346(9) Uani 1 1 d . . . H12 H 0.9981 0.2667 0.9162 0.041 Uiso 1 1 calc R . . C11 C 0.85592(19) -0.0082(5) 0.69548(19) 0.0334(8) Uani 1 1 d . . . H8 H 0.8470 -0.0782 0.7345 0.040 Uiso 1 1 calc R . . C15 C 0.8692(2) 0.4637(4) 0.86547(19) 0.0330(9) Uani 1 1 d . . . H11 H 0.8778 0.3809 0.9051 0.040 Uiso 1 1 calc R . . C17 C 0.9339(2) 0.7456(5) 0.8823(2) 0.0426(10) Uani 1 1 d . . . H18 H 0.8809 0.7904 0.8690 0.051 Uiso 1 1 calc R . . C2 C 0.7098(2) -0.4549(5) 0.6337(2) 0.0486(11) Uani 1 1 d . . . H2 H 0.7258 -0.5481 0.6637 0.058 Uiso 1 1 calc R . . C14 C 0.7860(2) 0.5440(5) 0.8539(2) 0.0434(10) Uani 1 1 d . . . H14A H 0.7759 0.6260 0.8153 0.065 Uiso 1 1 calc R . . H14B H 0.7859 0.5952 0.8997 0.065 Uiso 1 1 calc R . . H14C H 0.7433 0.4616 0.8395 0.065 Uiso 1 1 calc R . . C1 C 0.6384(2) -0.4588(6) 0.5699(2) 0.0532(12) Uani 1 1 d . . . H1 H 0.6065 -0.5542 0.5580 0.064 Uiso 1 1 calc R . . C24 C 1.1871(2) 0.3864(5) 0.9472(2) 0.0428(10) Uani 1 1 d . . . H14 H 1.2402 0.3435 0.9576 0.051 Uiso 1 1 calc R . . C19 C 1.0798(3) 0.7909(5) 0.9127(2) 0.0494(11) Uani 1 1 d . . . H16 H 1.1243 0.8617 0.9188 0.059 Uiso 1 1 calc R . . C18 C 1.0030(3) 0.8531(5) 0.8959(2) 0.0561(12) Uani 1 1 d . . . H17 H 0.9950 0.9667 0.8931 0.067 Uiso 1 1 calc R . . S2 S 0.55140(5) 1.00467(13) 0.73198(5) 0.0413(3) Uani 1 1 d . . . O1 O 0.46337(14) 0.9498(3) 0.69411(13) 0.0434(7) Uani 1 1 d . . . C27 C 0.5830(2) 1.1025(6) 0.6618(2) 0.0503(10) Uani 1 1 d . . . H27A H 0.5734 1.0298 0.6198 0.075 Uiso 1 1 calc R . . H27B H 0.6409 1.1285 0.6816 0.075 Uiso 1 1 calc R . . H27C H 0.5518 1.2023 0.6462 0.075 Uiso 1 1 calc R . . C28 C 0.6121(2) 0.8223(6) 0.7404(3) 0.0584(12) Uani 1 1 d . . . H28A H 0.6039 0.7524 0.7784 0.088 Uiso 1 1 calc R . . H28B H 0.6696 0.8517 0.7539 0.088 Uiso 1 1 calc R . . H28C H 0.5956 0.7647 0.6935 0.088 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 0.0394(5) 0.0384(6) 0.0481(6) 0.0018(5) 0.0229(4) -0.0045(5) C10 0.0293(17) 0.033(2) 0.0319(18) 0.0002(17) 0.0159(14) 0.0072(17) N1 0.0430(18) 0.0301(18) 0.0393(17) -0.0022(14) 0.0225(14) -0.0069(13) C21 0.0410(19) 0.0285(19) 0.0202(15) -0.0006(16) 0.0118(14) 0.0031(17) C12 0.0176(16) 0.037(2) 0.0286(18) 0.0005(16) 0.0057(14) 0.0040(14) C16 0.0391(19) 0.028(2) 0.0255(18) -0.0009(15) 0.0108(15) 0.0016(16) C4 0.0313(18) 0.039(2) 0.0263(18) -0.0044(16) 0.0157(15) 0.0076(17) N2 0.0312(15) 0.0295(18) 0.0273(15) 0.0029(13) 0.0134(12) 0.0002(13) C3 0.039(2) 0.032(2) 0.040(2) -0.0043(18) 0.0126(17) -0.0016(17) C25 0.036(2) 0.056(3) 0.031(2) -0.0079(18) 0.0091(16) -0.0099(18) C8 0.041(2) 0.057(3) 0.036(2) 0.017(2) 0.0164(17) 0.017(2) C6 0.032(2) 0.067(3) 0.042(2) -0.017(2) 0.0111(18) -0.002(2) C5 0.033(2) 0.056(3) 0.035(2) -0.008(2) 0.0173(17) 0.008(2) C9 0.040(2) 0.039(2) 0.042(2) 0.003(2) 0.0237(17) 0.0027(19) C23 0.045(2) 0.033(2) 0.046(2) -0.0044(18) 0.0097(19) 0.0078(18) C7 0.0306(19) 0.076(3) 0.0288(19) 0.001(2) 0.0088(15) 0.013(2) C13 0.033(2) 0.051(3) 0.055(3) -0.013(2) 0.0128(19) 0.0034(18) C20 0.041(2) 0.039(2) 0.0226(17) -0.0050(17) 0.0082(15) -0.0066(19) C22 0.038(2) 0.034(2) 0.032(2) -0.0066(17) 0.0110(16) 0.0001(17) C11 0.0366(18) 0.0276(19) 0.0386(19) 0.0002(17) 0.0157(15) 0.0035(17) C15 0.0384(19) 0.033(2) 0.0316(19) 0.0067(16) 0.0164(15) 0.0093(16) C17 0.047(2) 0.035(2) 0.041(2) 0.0027(19) 0.0078(18) 0.0105(19) C2 0.056(2) 0.037(3) 0.057(3) -0.002(2) 0.024(2) 0.004(2) C14 0.040(2) 0.049(3) 0.046(2) 0.0020(19) 0.0215(18) 0.0124(18) C1 0.050(2) 0.051(3) 0.063(3) -0.017(3) 0.024(2) -0.012(2) C24 0.032(2) 0.049(3) 0.045(2) -0.015(2) 0.0110(18) 0.0051(19) C19 0.058(3) 0.034(2) 0.048(3) 0.001(2) 0.006(2) -0.012(2) C18 0.067(3) 0.026(2) 0.064(3) 0.005(2) 0.007(2) 0.002(2) S2 0.0373(5) 0.0531(6) 0.0371(5) -0.0051(5) 0.0171(4) -0.0031(5) O1 0.0295(13) 0.0617(19) 0.0415(15) 0.0089(13) 0.0151(11) -0.0014(12) C27 0.038(2) 0.053(3) 0.067(3) 0.014(2) 0.0271(19) 0.005(2) C28 0.039(2) 0.064(3) 0.073(3) 0.024(3) 0.019(2) 0.011(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 S1 C12 1.678(3) . ? C10 C9 1.353(5) . ? C10 C4 1.438(5) . ? C10 C11 1.522(4) . ? N1 C12 1.342(4) . ? N1 C11 1.449(5) . ? C21 C22 1.423(5) . ? C21 C20 1.425(5) . ? C21 C16 1.425(4) . ? C12 N2 1.351(4) . ? C16 C17 1.354(5) . ? C16 C15 1.520(5) . ? C4 C3 1.388(5) . ? C4 C5 1.436(5) . ? N2 C15 1.464(4) . ? C3 C2 1.360(5) . ? C25 C24 1.355(5) . ? C25 C20 1.421(5) . ? C8 C7 1.344(6) . ? C8 C9 1.405(5) . ? C6 C1 1.346(6) . ? C6 C5 1.405(6) . ? C5 C7 1.423(6) . ? C23 C22 1.355(5) . ? C23 C24 1.403(5) . ? C13 C11 1.531(5) . ? C20 C19 1.410(6) . ? C15 C14 1.514(4) . ? C17 C18 1.421(6) . ? C2 C1 1.409(5) . ? C19 C18 1.343(6) . ? S2 O1 1.507(2) . ? S2 C27 1.773(4) . ? S2 C28 1.782(4) . ? 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 C9 C10 C4 119.8(3) . . ? C9 C10 C11 121.1(3) . . ? C4 C10 C11 119.0(3) . . ? C12 N1 C11 124.6(3) . . ? C22 C21 C20 117.3(3) . . ? C22 C21 C16 123.6(3) . . ? C20 C21 C16 119.0(3) . . ? N1 C12 N2 114.4(3) . . ? N1 C12 S1 123.9(3) . . ? N2 C12 S1 121.7(3) . . ? C17 C16 C21 119.1(3) . . ? C17 C16 C15 121.7(3) . . ? C21 C16 C15 119.0(3) . . ? C3 C4 C5 117.1(4) . . ? C3 C4 C10 124.8(3) . . ? C5 C4 C10 118.1(3) . . ? C12 N2 C15 125.3(3) . . ? C2 C3 C4 122.9(4) . . ? C24 C25 C20 121.1(4) . . ? C7 C8 C9 120.5(4) . . ? C1 C6 C5 121.8(4) . . ? C6 C5 C7 122.3(3) . . ? C6 C5 C4 118.8(4) . . ? C7 C5 C4 118.9(4) . . ? C10 C9 C8 121.8(4) . . ? C22 C23 C24 121.2(4) . . ? C8 C7 C5 120.9(3) . . ? C19 C20 C25 121.4(4) . . ? C19 C20 C21 119.2(3) . . ? C25 C20 C21 119.3(4) . . ? C23 C22 C21 121.3(4) . . ? N1 C11 C10 112.7(3) . . ? N1 C11 C13 109.0(3) . . ? C10 C11 C13 110.6(3) . . ? N2 C15 C14 111.5(3) . . ? N2 C15 C16 106.5(3) . . ? C14 C15 C16 115.5(3) . . ? C16 C17 C18 121.6(4) . . ? C3 C2 C1 119.5(4) . . ? C6 C1 C2 119.7(4) . . ? C25 C24 C23 119.6(4) . . ? C18 C19 C20 120.7(4) . . ? C19 C18 C17 120.2(4) . . ? O1 S2 C27 106.06(17) . . ? O1 S2 C28 105.05(19) . . ? C27 S2 C28 97.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C12 N2 -178.3(3) . . . . ? C11 N1 C12 S1 0.8(5) . . . . ? C22 C21 C16 C17 176.9(4) . . . . ? C20 C21 C16 C17 -3.7(5) . . . . ? C22 C21 C16 C15 -8.4(4) . . . . ? C20 C21 C16 C15 171.1(3) . . . . ? C9 C10 C4 C3 179.5(3) . . . . ? C11 C10 C4 C3 1.3(5) . . . . ? C9 C10 C4 C5 -0.9(5) . . . . ? C11 C10 C4 C5 -179.1(3) . . . . ? N1 C12 N2 C15 -166.2(3) . . . . ? S1 C12 N2 C15 14.8(4) . . . . ? C5 C4 C3 C2 -1.8(5) . . . . ? C10 C4 C3 C2 177.8(3) . . . . ? C1 C6 C5 C7 179.3(4) . . . . ? C1 C6 C5 C4 0.0(6) . . . . ? C3 C4 C5 C6 1.5(5) . . . . ? C10 C4 C5 C6 -178.2(3) . . . . ? C3 C4 C5 C7 -177.9(3) . . . . ? C10 C4 C5 C7 2.5(5) . . . . ? C4 C10 C9 C8 -1.4(5) . . . . ? C11 C10 C9 C8 176.8(3) . . . . ? C7 C8 C9 C10 2.1(5) . . . . ? C9 C8 C7 C5 -0.3(5) . . . . ? C6 C5 C7 C8 178.8(3) . . . . ? C4 C5 C7 C8 -1.9(5) . . . . ? C24 C25 C20 C19 179.5(4) . . . . ? C24 C25 C20 C21 -2.0(5) . . . . ? C22 C21 C20 C19 -178.1(3) . . . . ? C16 C21 C20 C19 2.4(5) . . . . ? C22 C21 C20 C25 3.4(5) . . . . ? C16 C21 C20 C25 -176.1(3) . . . . ? C24 C23 C22 C21 -1.7(6) . . . . ? C20 C21 C22 C23 -1.6(5) . . . . ? C16 C21 C22 C23 177.9(3) . . . . ? C12 N1 C11 C10 95.3(4) . . . . ? C12 N1 C11 C13 -141.5(3) . . . . ? C9 C10 C11 N1 26.8(4) . . . . ? C4 C10 C11 N1 -155.1(3) . . . . ? C9 C10 C11 C13 -95.6(4) . . . . ? C4 C10 C11 C13 82.6(4) . . . . ? C12 N2 C15 C14 -89.8(4) . . . . ? C12 N2 C15 C16 143.4(3) . . . . ? C17 C16 C15 N2 110.3(4) . . . . ? C21 C16 C15 N2 -64.3(3) . . . . ? C17 C16 C15 C14 -14.1(5) . . . . ? C21 C16 C15 C14 171.3(3) . . . . ? C21 C16 C17 C18 1.4(6) . . . . ? C15 C16 C17 C18 -173.2(3) . . . . ? C4 C3 C2 C1 0.6(6) . . . . ? C5 C6 C1 C2 -1.2(6) . . . . ? C3 C2 C1 C6 1.0(6) . . . . ? C20 C25 C24 C23 -1.3(6) . . . . ? C22 C23 C24 C25 3.2(6) . . . . ? C25 C20 C19 C18 179.7(4) . . . . ? C21 C20 C19 C18 1.2(6) . . . . ? C20 C19 C18 C17 -3.5(6) . . . . ? C16 C17 C18 C19 2.2(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.533 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.048