# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 N O3' _chemical_formula_sum 'C20 H15 N O3' _chemical_formula_weight 317.33 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 13.893(6) _cell_length_b 10.823(5) _cell_length_c 10.819(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.183(6) _cell_angle_gamma 90.00 _cell_volume 1562.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3670 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 28.0 _exptl_crystal_description rectangular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 kappa apex ccd' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16666 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3670 _reflns_number_gt 2852 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0701P)^2^+0.1923P] 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 3670 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C9 C 0.38477(9) 0.13965(11) 0.06253(10) 0.0420(3) Uani 1 1 d . . . N1 N 0.70202(8) 0.14537(11) 0.16535(10) 0.0526(3) Uani 1 1 d . . . C10 C 0.49094(9) 0.14207(10) 0.09656(10) 0.0393(3) Uani 1 1 d . . . C1 C 0.54120(9) 0.23827(11) 0.05100(11) 0.0429(3) Uani 1 1 d . . . C8 C 0.54561(9) 0.04584(11) 0.17375(10) 0.0431(3) Uani 1 1 d . . . C5 C 0.33646(10) 0.04014(12) 0.10535(12) 0.0488(3) Uani 1 1 d . . . C12 C 0.65631(10) 0.04727(12) 0.21068(12) 0.0499(3) Uani 1 1 d . . . C4 C 0.33180(9) 0.23668(12) -0.01704(12) 0.0476(3) Uani 1 1 d . . . C2 C 0.48633(10) 0.32907(12) -0.02656(12) 0.0495(3) Uani 1 1 d . . . C3 C 0.38139(10) 0.32954(13) -0.06042(13) 0.0534(3) Uani 1 1 d . . . O3 O 0.23002(7) 0.22746(10) -0.04508(10) 0.0652(3) Uani 1 1 d . . . C6 C 0.39115(11) -0.05241(13) 0.17816(12) 0.0537(3) Uani 1 1 d . . . C11 C 0.65119(10) 0.24029(12) 0.08499(12) 0.0501(3) Uani 1 1 d . . . C7 C 0.49645(11) -0.05005(12) 0.21291(11) 0.0502(3) Uani 1 1 d . . . C15 C 0.17041(9) 0.31178(13) -0.13265(13) 0.0544(3) Uani 1 1 d . . . C13 C 0.81261(11) 0.14669(19) 0.20283(17) 0.0672(4) Uani 1 1 d . . . C20 C 0.13680(12) 0.27736(17) -0.26011(15) 0.0675(4) Uani 1 1 d . . . C18 C 0.04480(12) 0.46622(18) -0.30239(18) 0.0750(5) Uani 1 1 d . . . C16 C 0.14370(13) 0.42096(16) -0.08803(17) 0.0721(5) Uani 1 1 d . . . C19 C 0.07286(13) 0.35626(19) -0.34491(16) 0.0764(5) Uani 1 1 d . . . C17 C 0.08028(15) 0.49894(17) -0.1748(2) 0.0822(5) Uani 1 1 d . . . O2 O 0.70662(8) -0.03290(10) 0.27754(10) 0.0692(3) Uani 1 1 d . . . O1 O 0.69784(8) 0.32032(11) 0.04751(11) 0.0736(3) Uani 1 1 d . . . C14 C 0.85537(14) 0.2108(2) 0.33044(19) 0.0771(5) Uani 1 1 d . . . H5 H 0.2650(12) 0.0385(13) 0.0840(14) 0.058(4) Uiso 1 1 d . . . H3 H 0.3453(11) 0.3935(15) -0.1121(14) 0.064(4) Uiso 1 1 d . . . H2 H 0.5224(11) 0.3928(14) -0.0570(13) 0.056(4) Uiso 1 1 d . . . H7 H 0.5357(11) -0.1168(15) 0.2654(14) 0.062(4) Uiso 1 1 d . . . H6 H 0.3555(12) -0.1209(15) 0.2062(14) 0.066(4) Uiso 1 1 d . . . H13B H 0.8299(13) 0.1875(17) 0.1309(18) 0.080(5) Uiso 1 1 d . . . H14B H 0.8324(15) 0.300(2) 0.3298(18) 0.094(6) Uiso 1 1 d . . . H18 H 0.0003(14) 0.5225(17) -0.3613(18) 0.083(5) Uiso 1 1 d . . . H14A H 0.9299(16) 0.2092(18) 0.3498(18) 0.098(6) Uiso 1 1 d . . . H14C H 0.8314(15) 0.1719(19) 0.3993(19) 0.097(6) Uiso 1 1 d . . . H13A H 0.8354(14) 0.0569(19) 0.2043(17) 0.088(6) Uiso 1 1 d . . . H20 H 0.1593(16) 0.199(2) -0.2863(19) 0.106(7) Uiso 1 1 d . . . H17 H 0.0633(16) 0.570(2) -0.145(2) 0.097(6) Uiso 1 1 d . . . H16 H 0.1659(14) 0.4413(17) -0.0027(19) 0.082(5) Uiso 1 1 d . . . H19 H 0.0476(15) 0.332(2) -0.437(2) 0.103(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C9 0.0477(6) 0.0440(6) 0.0335(5) 0.0001(4) 0.0098(5) -0.0019(5) N1 0.0430(6) 0.0620(7) 0.0520(6) -0.0061(5) 0.0117(5) 0.0032(5) C10 0.0467(6) 0.0400(6) 0.0307(5) -0.0046(4) 0.0097(4) -0.0009(5) C1 0.0472(6) 0.0449(6) 0.0370(6) -0.0043(5) 0.0125(5) -0.0020(5) C8 0.0517(7) 0.0434(6) 0.0328(5) -0.0052(4) 0.0094(5) 0.0031(5) C5 0.0500(7) 0.0535(7) 0.0421(6) 0.0018(5) 0.0115(5) -0.0062(6) C12 0.0523(7) 0.0519(7) 0.0422(6) -0.0076(5) 0.0078(5) 0.0073(6) C4 0.0433(6) 0.0542(7) 0.0424(6) 0.0047(5) 0.0072(5) -0.0015(5) C2 0.0552(7) 0.0469(7) 0.0475(7) 0.0045(5) 0.0161(6) -0.0056(6) C3 0.0542(8) 0.0521(7) 0.0498(7) 0.0136(6) 0.0079(6) 0.0025(6) O3 0.0442(5) 0.0730(7) 0.0722(6) 0.0283(5) 0.0058(4) -0.0005(4) C6 0.0650(8) 0.0498(7) 0.0461(7) 0.0062(5) 0.0151(6) -0.0088(6) C11 0.0496(7) 0.0549(7) 0.0482(7) -0.0059(6) 0.0176(5) -0.0028(6) C7 0.0642(8) 0.0449(7) 0.0387(6) 0.0040(5) 0.0100(5) 0.0032(6) C15 0.0399(6) 0.0610(8) 0.0566(7) 0.0141(6) 0.0043(5) -0.0023(6) C13 0.0441(8) 0.0836(12) 0.0727(10) -0.0027(8) 0.0142(7) 0.0048(7) C20 0.0641(9) 0.0767(11) 0.0591(9) 0.0049(8) 0.0128(7) 0.0056(8) C18 0.0513(8) 0.0785(11) 0.0824(11) 0.0315(9) -0.0023(7) -0.0013(8) C16 0.0741(10) 0.0646(9) 0.0646(10) -0.0009(8) -0.0022(8) -0.0030(8) C19 0.0677(10) 0.0967(14) 0.0552(9) 0.0114(9) 0.0011(7) -0.0017(9) C17 0.0801(11) 0.0580(10) 0.0980(14) 0.0063(9) 0.0072(10) 0.0085(9) O2 0.0620(6) 0.0651(6) 0.0704(6) 0.0056(5) 0.0015(5) 0.0164(5) O1 0.0564(6) 0.0777(7) 0.0911(8) 0.0117(6) 0.0276(6) -0.0098(5) C14 0.0544(9) 0.0903(13) 0.0783(11) -0.0066(10) 0.0048(8) -0.0101(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 C5 1.4138(17) . ? C9 C10 1.4175(17) . ? C9 C4 1.4256(17) . ? N1 C12 1.3945(18) . ? N1 C11 1.4027(18) . ? N1 C13 1.4759(19) . ? C10 C8 1.4160(16) . ? C10 C1 1.4165(17) . ? C1 C2 1.3764(18) . ? C1 C11 1.4689(19) . ? C8 C7 1.3727(18) . ? C8 C12 1.4775(19) . ? C5 C6 1.3666(19) . ? C5 H5 0.954(15) . ? C12 O2 1.2177(16) . ? C4 O3 1.3647(17) . ? C4 C3 1.3731(18) . ? C2 C3 1.401(2) . ? C2 H2 0.963(15) . ? C3 H3 0.942(16) . ? O3 C15 1.4068(16) . ? C6 C7 1.406(2) . ? C6 H6 0.985(16) . ? C11 O1 1.2170(17) . ? C7 H7 0.984(15) . ? C15 C16 1.366(2) . ? C15 C20 1.378(2) . ? C13 C14 1.511(3) . ? C13 H13B 0.981(19) . ? C13 H13A 1.02(2) . ? C20 C19 1.380(2) . ? C20 H20 0.97(2) . ? C18 C19 1.371(3) . ? C18 C17 1.376(3) . ? C18 H18 0.970(19) . ? C16 C17 1.382(2) . ? C16 H16 0.915(19) . ? C19 H19 1.00(2) . ? C17 H17 0.89(2) . ? C14 H14B 1.01(2) . ? C14 H14A 1.00(2) . ? C14 H14C 0.99(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C9 C10 118.93(11) . . ? C5 C9 C4 123.14(11) . . ? C10 C9 C4 117.91(10) . . ? C12 N1 C11 125.15(11) . . ? C12 N1 C13 116.87(12) . . ? C11 N1 C13 117.96(12) . . ? C8 C10 C1 120.69(11) . . ? C8 C10 C9 119.20(11) . . ? C1 C10 C9 120.09(10) . . ? C2 C1 C10 119.60(12) . . ? C2 C1 C11 120.19(11) . . ? C10 C1 C11 120.21(11) . . ? C7 C8 C10 120.46(12) . . ? C7 C8 C12 119.63(11) . . ? C10 C8 C12 119.91(11) . . ? C6 C5 C9 120.58(12) . . ? C6 C5 H5 120.0(9) . . ? C9 C5 H5 119.5(9) . . ? O2 C12 N1 120.61(13) . . ? O2 C12 C8 122.35(13) . . ? N1 C12 C8 117.04(11) . . ? O3 C4 C3 124.41(11) . . ? O3 C4 C9 114.14(11) . . ? C3 C4 C9 121.45(12) . . ? C1 C2 C3 121.42(12) . . ? C1 C2 H2 117.9(9) . . ? C3 C2 H2 120.7(9) . . ? C4 C3 C2 119.53(12) . . ? C4 C3 H3 120.4(10) . . ? C2 C3 H3 120.1(9) . . ? C4 O3 C15 118.77(10) . . ? C5 C6 C7 120.72(12) . . ? C5 C6 H6 118.8(9) . . ? C7 C6 H6 120.4(9) . . ? O1 C11 N1 120.33(12) . . ? O1 C11 C1 122.72(13) . . ? N1 C11 C1 116.94(11) . . ? C8 C7 C6 120.10(12) . . ? C8 C7 H7 119.3(9) . . ? C6 C7 H7 120.6(9) . . ? C16 C15 C20 122.52(14) . . ? C16 C15 O3 119.34(13) . . ? C20 C15 O3 118.05(14) . . ? N1 C13 C14 111.70(14) . . ? N1 C13 H13B 104.7(10) . . ? C14 C13 H13B 113.4(10) . . ? N1 C13 H13A 106.9(11) . . ? C14 C13 H13A 112.4(10) . . ? H13B C13 H13A 107.3(15) . . ? C15 C20 C19 118.27(17) . . ? C15 C20 H20 118.8(12) . . ? C19 C20 H20 123.0(12) . . ? C19 C18 C17 120.26(15) . . ? C19 C18 H18 120.9(11) . . ? C17 C18 H18 118.8(11) . . ? C15 C16 C17 118.21(17) . . ? C15 C16 H16 121.1(12) . . ? C17 C16 H16 120.7(12) . . ? C18 C19 C20 120.29(16) . . ? C18 C19 H19 120.7(12) . . ? C20 C19 H19 119.0(13) . . ? C18 C17 C16 120.45(19) . . ? C18 C17 H17 121.9(14) . . ? C16 C17 H17 117.7(14) . . ? C13 C14 H14B 112.8(11) . . ? C13 C14 H14A 107.8(11) . . ? H14B C14 H14A 108.9(16) . . ? C13 C14 H14C 111.3(11) . . ? H14B C14 H14C 103.7(18) . . ? H14A C14 H14C 112.4(16) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.220 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 936315' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 N O3 S2' _chemical_formula_sum 'C25 H25 N O3 S2' _chemical_formula_weight 451.58 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 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 8.6529(7) _cell_length_b 8.6955(7) _cell_length_c 15.3316(12) _cell_angle_alpha 87.905(2) _cell_angle_beta 76.192(2) _cell_angle_gamma 87.453(2) _cell_volume 1118.73(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6596 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 30.74 _exptl_crystal_description rectangular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8158 _exptl_absorpt_correction_T_max 0.9013 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11706 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 30.20 _reflns_number_total 6596 _reflns_number_gt 3164 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0891P)^2^+0.0994P] 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_number_reflns 6596 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1508 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1947 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.28344(10) 1.44886(8) 0.29672(5) 0.0666(3) Uani 1 1 d . . . S2 S 0.15920(9) 1.25400(8) 0.45802(4) 0.0591(2) Uani 1 1 d . . . O1 O 1.1068(2) 0.7963(2) -0.19661(13) 0.0636(5) Uani 1 1 d . . . O2 O 1.0196(2) 0.2847(2) -0.17847(13) 0.0722(6) Uani 1 1 d . . . O3 O 0.5203(2) 0.77047(19) 0.14619(12) 0.0607(5) Uani 1 1 d . . . N1 N 1.0703(2) 0.5386(2) -0.18266(13) 0.0476(5) Uani 1 1 d . . . C13 C 1.2123(3) 0.5141(3) -0.25742(17) 0.0583(7) Uani 1 1 d . . . H13A H 1.2542 0.4095 -0.2532 0.070 Uiso 1 1 calc R . . H13B H 1.2938 0.5835 -0.2516 0.070 Uiso 1 1 calc R . . C14 C 1.1758(4) 0.5409(4) -0.34768(19) 0.0809(10) Uani 1 1 d . . . H14A H 1.2712 0.5242 -0.3939 0.121 Uiso 1 1 calc R . . H14B H 1.1358 0.6448 -0.3525 0.121 Uiso 1 1 calc R . . H14C H 1.0972 0.4707 -0.3544 0.121 Uiso 1 1 calc R . . C11 C 1.0313(3) 0.6911(3) -0.15594(16) 0.0460(6) Uani 1 1 d . . . C1 C 0.8973(3) 0.7141(3) -0.07753(15) 0.0406(5) Uani 1 1 d . . . C10 C 0.8104(3) 0.5868(2) -0.03426(14) 0.0363(5) Uani 1 1 d . . . C8 C 0.8498(3) 0.4369(2) -0.06731(15) 0.0401(5) Uani 1 1 d . . . C12 C 0.9837(3) 0.4112(3) -0.14641(16) 0.0490(6) Uani 1 1 d . . . C7 C 0.7642(3) 0.3143(3) -0.02449(16) 0.0475(6) Uani 1 1 d . . . H7 H 0.7902 0.2157 -0.0463 0.057 Uiso 1 1 calc R . . C6 C 0.6399(3) 0.3359(3) 0.05076(16) 0.0489(6) Uani 1 1 d . . . H6 H 0.5835 0.2520 0.0790 0.059 Uiso 1 1 calc R . . C5 C 0.6001(3) 0.4806(3) 0.08352(15) 0.0427(6) Uani 1 1 d . . . H5 H 0.5163 0.4943 0.1337 0.051 Uiso 1 1 calc R . . C9 C 0.6844(3) 0.6082(2) 0.04203(14) 0.0372(5) Uani 1 1 d . . . C4 C 0.6483(3) 0.7609(3) 0.07346(16) 0.0451(6) Uani 1 1 d . . . C3 C 0.7327(3) 0.8827(3) 0.03103(18) 0.0561(7) Uani 1 1 d . . . H3 H 0.7069 0.9817 0.0522 0.067 Uiso 1 1 calc R . . C2 C 0.8577(3) 0.8577(3) -0.04424(16) 0.0508(6) Uani 1 1 d . . . H2 H 0.9154 0.9409 -0.0723 0.061 Uiso 1 1 calc R . . C15 C 0.4832(3) 0.9055(3) 0.19508(16) 0.0480(6) Uani 1 1 d . . . C16 C 0.5909(3) 0.9725(3) 0.23276(17) 0.0524(7) Uani 1 1 d . . . H16 H 0.6962 0.9359 0.2217 0.063 Uiso 1 1 calc R . . C17 C 0.5385(3) 1.0977(3) 0.28834(17) 0.0499(6) Uani 1 1 d . . . H17 H 0.6103 1.1448 0.3143 0.060 Uiso 1 1 calc R . . C18 C 0.3820(3) 1.1528(3) 0.30555(15) 0.0449(6) Uani 1 1 d . . . C19 C 0.2774(3) 1.0819(3) 0.26635(16) 0.0531(7) Uani 1 1 d . . . H19 H 0.1722 1.1185 0.2771 0.064 Uiso 1 1 calc R . . C20 C 0.3255(3) 0.9578(3) 0.21153(17) 0.0542(7) Uani 1 1 d . . . H20 H 0.2534 0.9101 0.1861 0.065 Uiso 1 1 calc R . . C21 C 0.3300(3) 1.2888(3) 0.36605(16) 0.0502(6) Uani 1 1 d . . . H21 H 0.4192 1.3159 0.3909 0.060 Uiso 1 1 calc R . . C22 C 0.2397(4) 1.6073(3) 0.3732(2) 0.0780(10) Uani 1 1 d . . . H22A H 0.1971 1.6939 0.3435 0.094 Uiso 1 1 calc R . . H22B H 0.1571 1.5770 0.4250 0.094 Uiso 1 1 calc R . . C23 C 0.3785(5) 1.6595(4) 0.4055(3) 0.0977(12) Uani 1 1 d . . . H23A H 0.3447 1.7436 0.4453 0.147 Uiso 1 1 calc R . . H23B H 0.4602 1.6926 0.3550 0.147 Uiso 1 1 calc R . . H23C H 0.4197 1.5758 0.4369 0.147 Uiso 1 1 calc R . . C24 C 0.2435(4) 1.1116(4) 0.5250(2) 0.0786(9) Uani 1 1 d . . . H24A H 0.2823 1.0215 0.4896 0.094 Uiso 1 1 calc R . . H24B H 0.3326 1.1540 0.5430 0.094 Uiso 1 1 calc R . . C25 C 0.1186(4) 1.0667(4) 0.6064(2) 0.0892(11) Uani 1 1 d . . . H25A H 0.1628 0.9909 0.6416 0.134 Uiso 1 1 calc R . . H25B H 0.0308 1.0246 0.5882 0.134 Uiso 1 1 calc R . . H25C H 0.0819 1.1559 0.6418 0.134 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 0.0741(5) 0.0537(4) 0.0570(4) 0.0044(3) 0.0107(4) 0.0096(4) S2 0.0643(5) 0.0554(4) 0.0469(4) -0.0022(3) 0.0065(3) 0.0081(3) O1 0.0605(12) 0.0539(11) 0.0630(12) 0.0037(9) 0.0124(10) -0.0098(9) O2 0.0867(15) 0.0480(11) 0.0683(13) -0.0224(10) 0.0098(11) 0.0067(10) O3 0.0661(12) 0.0429(10) 0.0575(11) -0.0151(8) 0.0184(9) -0.0031(9) N1 0.0446(12) 0.0497(12) 0.0420(11) -0.0061(9) 0.0020(9) 0.0052(10) C13 0.0487(16) 0.0641(17) 0.0530(16) -0.0080(13) 0.0049(13) 0.0081(14) C14 0.074(2) 0.115(3) 0.0478(17) -0.0113(17) -0.0014(15) 0.000(2) C11 0.0465(15) 0.0476(14) 0.0406(13) -0.0013(11) -0.0042(11) 0.0020(12) C1 0.0432(14) 0.0370(12) 0.0376(12) -0.0007(10) -0.0019(10) -0.0003(10) C10 0.0401(13) 0.0328(11) 0.0352(11) -0.0024(9) -0.0082(10) 0.0026(10) C8 0.0459(14) 0.0347(12) 0.0390(12) -0.0040(9) -0.0090(11) 0.0025(10) C12 0.0554(16) 0.0449(14) 0.0432(14) -0.0061(11) -0.0050(12) 0.0054(12) C7 0.0625(17) 0.0312(12) 0.0477(14) -0.0061(10) -0.0102(13) 0.0005(11) C6 0.0602(17) 0.0366(13) 0.0478(14) 0.0049(11) -0.0083(13) -0.0113(12) C5 0.0449(14) 0.0426(13) 0.0363(12) -0.0010(10) -0.0012(10) -0.0025(11) C9 0.0419(13) 0.0343(12) 0.0349(11) -0.0014(9) -0.0083(10) -0.0004(10) C4 0.0491(15) 0.0386(13) 0.0407(13) -0.0067(10) 0.0026(11) 0.0041(11) C3 0.0708(19) 0.0320(12) 0.0533(15) -0.0048(11) 0.0096(14) 0.0014(12) C2 0.0618(17) 0.0338(12) 0.0483(14) 0.0031(10) 0.0033(13) -0.0044(12) C15 0.0534(16) 0.0390(13) 0.0412(13) -0.0054(10) 0.0087(12) 0.0034(12) C16 0.0396(14) 0.0468(14) 0.0618(16) -0.0084(12) 0.0054(12) 0.0058(12) C17 0.0474(15) 0.0451(14) 0.0536(15) -0.0096(12) -0.0037(12) -0.0008(12) C18 0.0443(14) 0.0427(13) 0.0414(13) -0.0039(10) 0.0021(11) 0.0009(11) C19 0.0450(15) 0.0595(16) 0.0500(15) -0.0118(12) -0.0031(12) 0.0145(12) C20 0.0568(17) 0.0607(16) 0.0434(14) -0.0090(12) -0.0085(12) 0.0017(14) C21 0.0507(15) 0.0456(14) 0.0476(14) -0.0087(11) 0.0019(12) 0.0037(12) C22 0.081(2) 0.0461(16) 0.089(2) 0.0000(15) 0.0130(19) 0.0100(16) C23 0.113(3) 0.062(2) 0.106(3) -0.009(2) 0.001(2) -0.013(2) C24 0.086(2) 0.071(2) 0.074(2) 0.0110(17) -0.0124(19) 0.0061(18) C25 0.103(3) 0.088(2) 0.074(2) 0.0213(19) -0.018(2) -0.011(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C22 1.809(3) . ? S1 C21 1.809(3) . ? S2 C21 1.810(3) . ? S2 C24 1.818(3) . ? O1 C11 1.212(3) . ? O2 C12 1.218(3) . ? O3 C4 1.373(3) . ? O3 C15 1.400(3) . ? N1 C12 1.389(3) . ? N1 C11 1.405(3) . ? N1 C13 1.480(3) . ? C13 C14 1.499(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C11 C1 1.470(3) . ? C1 C2 1.364(3) . ? C1 C10 1.419(3) . ? C10 C9 1.407(3) . ? C10 C8 1.414(3) . ? C8 C7 1.379(3) . ? C8 C12 1.480(3) . ? C7 C6 1.389(3) . ? C7 H7 0.9300 . ? C6 C5 1.371(3) . ? C6 H6 0.9300 . ? C5 C9 1.403(3) . ? C5 H5 0.9300 . ? C9 C4 1.426(3) . ? C4 C3 1.367(3) . ? C3 C2 1.397(3) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C15 C16 1.368(4) . ? C15 C20 1.386(3) . ? C16 C17 1.398(3) . ? C16 H16 0.9300 . ? C17 C18 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.377(3) . ? C18 C21 1.515(3) . ? C19 C20 1.380(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21 0.9800 . ? C22 C23 1.499(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.496(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C22 S1 C21 103.52(14) . . ? C21 S2 C24 100.94(14) . . ? C4 O3 C15 121.21(19) . . ? C12 N1 C11 125.2(2) . . ? C12 N1 C13 118.0(2) . . ? C11 N1 C13 116.8(2) . . ? N1 C13 C14 112.4(2) . . ? N1 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N1 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C11 N1 120.3(2) . . ? O1 C11 C1 123.0(2) . . ? N1 C11 C1 116.7(2) . . ? C2 C1 C10 119.3(2) . . ? C2 C1 C11 120.3(2) . . ? C10 C1 C11 120.4(2) . . ? C9 C10 C8 119.3(2) . . ? C9 C10 C1 120.46(19) . . ? C8 C10 C1 120.3(2) . . ? C7 C8 C10 119.6(2) . . ? C7 C8 C12 120.1(2) . . ? C10 C8 C12 120.2(2) . . ? O2 C12 N1 120.6(2) . . ? O2 C12 C8 122.5(2) . . ? N1 C12 C8 116.9(2) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C5 C9 120.6(2) . . ? C6 C5 H5 119.7 . . ? C9 C5 H5 119.7 . . ? C5 C9 C10 119.4(2) . . ? C5 C9 C4 122.9(2) . . ? C10 C9 C4 117.7(2) . . ? C3 C4 O3 125.4(2) . . ? C3 C4 C9 121.3(2) . . ? O3 C4 C9 113.2(2) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C1 C2 C3 121.6(2) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C16 C15 C20 121.6(2) . . ? C16 C15 O3 122.3(2) . . ? C20 C15 O3 115.8(2) . . ? C15 C16 C17 118.2(2) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C18 C17 C16 121.4(2) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C19 C18 C17 118.5(2) . . ? C19 C18 C21 121.7(2) . . ? C17 C18 C21 119.8(2) . . ? C18 C19 C20 121.4(2) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C20 C15 118.8(3) . . ? C19 C20 H20 120.6 . . ? C15 C20 H20 120.6 . . ? C18 C21 S1 107.37(16) . . ? C18 C21 S2 114.00(17) . . ? S1 C21 S2 109.41(13) . . ? C18 C21 H21 108.6 . . ? S1 C21 H21 108.6 . . ? S2 C21 H21 108.6 . . ? C23 C22 S1 115.2(2) . . ? C23 C22 H22A 108.5 . . ? S1 C22 H22A 108.5 . . ? C23 C22 H22B 108.5 . . ? S1 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 S2 109.4(2) . . ? C25 C24 H24A 109.8 . . ? S2 C24 H24A 109.8 . . ? C25 C24 H24B 109.8 . . ? S2 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.20 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.421 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 936316'