# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Choon-Hong Tan' _publ_contact_author_email chmtanch@nus.edu.sg _publ_section_title ; Guanidine-Catalyzed Enantioselective Desymmetrization of meso-Aziridines ; loop_ _publ_author_name 'Yan Zhang' 'Choon Wee Kee' R.Lee 'Xiao Fu' 'J.Ying-Teck Soh' 'E.Mun Foong Loh' 'Kuo-Wei Huang' 'Choon-Hong Tan' # Attachment '- 4f.cif' data_9440 _database_code_depnum_ccdc_archive 'CCDC 806368' #TrackingRef '- 4f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cl2 N3 O5 S' _chemical_formula_weight 470.32 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4505(6) _cell_length_b 6.8838(5) _cell_length_c 17.8060(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.790(2) _cell_angle_gamma 90.00 _cell_volume 1013.95(13) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2453 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.22 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.461 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8895 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 7133 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3546 _reflns_number_gt 3371 _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^)+(0.0779P)^2^+0.0928P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(9) _refine_ls_number_reflns 3546 _refine_ls_number_parameters 274 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 0.78096(11) 0.63745(13) 0.32482(5) 0.0333(2) Uani 1 1 d . . . Cl1 Cl 0.39322(10) 0.59366(16) 0.27105(5) 0.0440(3) Uani 1 1 d . . . Cl2 Cl 0.98498(10) 0.58434(16) 0.19463(6) 0.0450(3) Uani 1 1 d . . . O1 O 1.1790(3) 0.2527(5) 0.37961(14) 0.0423(7) Uani 1 1 d . . . O2 O 1.5911(3) 0.0734(6) 0.24704(15) 0.0472(7) Uani 1 1 d . . . O3 O 1.5368(3) -0.0100(5) 0.12879(16) 0.0503(8) Uani 1 1 d . . . O4 O 0.9783(5) -0.1061(7) 0.00117(19) 0.0656(11) Uani 1 1 d . . . O5 O 0.7967(3) 0.0418(9) 0.04791(16) 0.0845(17) Uani 1 1 d . . . N1 N 0.9140(3) 0.2078(5) 0.33265(15) 0.0280(6) Uani 1 1 d D . . H1N H 0.836(4) 0.161(6) 0.2951(19) 0.042 Uiso 1 1 d D . . N2 N 1.4949(3) 0.0366(5) 0.18748(17) 0.0327(7) Uani 1 1 d . . . N3 N 0.9327(4) -0.0179(6) 0.05209(17) 0.0453(9) Uani 1 1 d . . . C1 C 0.6858(4) 0.5756(6) 0.23010(17) 0.0303(7) Uani 1 1 d . . . C2 C 0.7782(4) 0.5552(6) 0.17353(19) 0.0356(8) Uani 1 1 d . . . C3 C 0.7075(6) 0.5115(8) 0.0982(2) 0.0547(12) Uani 1 1 d . . . H3 H 0.7718 0.4967 0.0612 0.066 Uiso 1 1 calc R . . C4 C 0.5416(6) 0.4900(9) 0.0777(2) 0.0584(13) Uani 1 1 d . . . H4A H 0.4931 0.4602 0.0267 0.070 Uiso 1 1 calc R . . C5 C 0.4462(5) 0.5121(7) 0.1318(2) 0.0455(10) Uani 1 1 d . . . H5A H 0.3335 0.4965 0.1177 0.055 Uiso 1 1 calc R . . C6 C 0.5172(4) 0.5571(6) 0.2065(2) 0.0369(8) Uani 1 1 d . . . C7 C 0.7267(4) 0.4307(5) 0.38037(17) 0.0255(7) Uani 1 1 d . . . H7 H 0.6311 0.3650 0.3493 0.031 Uiso 1 1 calc R . . C8 C 0.6805(5) 0.5118(6) 0.45256(19) 0.0340(8) Uani 1 1 d . . . H8A H 0.7721 0.5839 0.4824 0.041 Uiso 1 1 calc R . . H8B H 0.5898 0.6022 0.4381 0.041 Uiso 1 1 calc R . . C9 C 0.6328(5) 0.3497(7) 0.5016(2) 0.0426(9) Uani 1 1 d . . . H9A H 0.6105 0.4051 0.5491 0.051 Uiso 1 1 calc R . . H9B H 0.5335 0.2877 0.4739 0.051 Uiso 1 1 calc R . . C10 C 0.7648(5) 0.1981(7) 0.5213(2) 0.0455(10) Uani 1 1 d . . . H10A H 0.7267 0.0908 0.5492 0.055 Uiso 1 1 calc R . . H10B H 0.8597 0.2558 0.5549 0.055 Uiso 1 1 calc R . . C11 C 0.8124(4) 0.1201(6) 0.44851(19) 0.0354(8) Uani 1 1 d . . . H11A H 0.9025 0.0287 0.4627 0.043 Uiso 1 1 calc R . . H11B H 0.7208 0.0496 0.4179 0.043 Uiso 1 1 calc R . . C12 C 0.8619(4) 0.2833(5) 0.40077(17) 0.0266(7) Uani 1 1 d . . . H12 H 0.9556 0.3502 0.4328 0.032 Uiso 1 1 calc R . . C13 C 1.0717(4) 0.2010(5) 0.32835(18) 0.0277(7) Uani 1 1 d . . . C14 C 1.1114(3) 0.1262(5) 0.25424(16) 0.0241(6) Uani 1 1 d . . . C15 C 1.2736(4) 0.1083(5) 0.25386(17) 0.0260(6) Uani 1 1 d . . . H15 H 1.3515 0.1354 0.2984 0.031 Uiso 1 1 calc R . . C16 C 1.3206(4) 0.0504(5) 0.18780(18) 0.0269(7) Uani 1 1 d . . . C17 C 1.2146(4) 0.0062(6) 0.12100(18) 0.0311(7) Uani 1 1 d . . . H17 H 1.2495 -0.0364 0.0769 0.037 Uiso 1 1 calc R . . C18 C 1.0535(4) 0.0283(6) 0.12275(17) 0.0294(7) Uani 1 1 d . . . C19 C 0.9969(4) 0.0869(6) 0.18724(17) 0.0289(7) Uani 1 1 d . . . H19 H 0.8856 0.0997 0.1859 0.035 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 0.0372(4) 0.0326(5) 0.0293(4) 0.0011(3) 0.0047(3) -0.0079(4) Cl1 0.0303(4) 0.0465(6) 0.0569(5) 0.0106(5) 0.0130(4) 0.0080(4) Cl2 0.0355(4) 0.0513(6) 0.0523(5) 0.0160(5) 0.0187(4) 0.0004(5) O1 0.0226(12) 0.076(2) 0.0266(12) -0.0150(12) 0.0004(9) -0.0031(13) O2 0.0216(11) 0.065(2) 0.0531(16) -0.0121(15) 0.0040(11) -0.0025(14) O3 0.0385(14) 0.074(2) 0.0441(15) -0.0007(15) 0.0206(12) 0.0054(15) O4 0.057(2) 0.104(3) 0.0356(14) -0.0334(17) 0.0109(14) -0.012(2) O5 0.0210(13) 0.193(5) 0.0368(15) -0.024(2) 0.0000(11) -0.008(2) N1 0.0206(13) 0.0409(17) 0.0214(13) -0.0057(12) 0.0018(10) 0.0012(12) N2 0.0221(13) 0.0356(18) 0.0413(16) 0.0029(13) 0.0087(12) 0.0034(12) N3 0.0351(17) 0.078(3) 0.0225(14) -0.0096(15) 0.0060(12) -0.0163(18) C1 0.0334(16) 0.0289(17) 0.0276(15) 0.0077(13) 0.0042(12) -0.0004(14) C2 0.0307(16) 0.043(2) 0.0338(17) 0.0098(16) 0.0079(13) 0.0020(16) C3 0.078(3) 0.063(3) 0.0266(17) 0.0054(19) 0.0167(19) 0.010(3) C4 0.061(3) 0.078(4) 0.0281(19) 0.004(2) -0.0106(19) 0.006(3) C5 0.0300(18) 0.052(3) 0.048(2) 0.0094(19) -0.0070(16) -0.0020(18) C6 0.0364(17) 0.036(2) 0.0381(18) 0.0096(16) 0.0063(14) 0.0042(16) C7 0.0288(16) 0.0274(17) 0.0209(14) 0.0004(12) 0.0066(12) -0.0018(13) C8 0.0368(18) 0.039(2) 0.0292(16) -0.0025(14) 0.0134(14) 0.0062(16) C9 0.049(2) 0.051(3) 0.0342(19) -0.0012(17) 0.0231(17) 0.003(2) C10 0.060(2) 0.053(3) 0.0259(17) 0.0106(17) 0.0149(16) 0.006(2) C11 0.0344(16) 0.041(2) 0.0316(16) 0.0055(16) 0.0086(13) 0.0082(17) C12 0.0210(14) 0.039(2) 0.0195(14) -0.0055(13) 0.0026(11) 0.0018(13) C13 0.0237(15) 0.0335(19) 0.0244(15) -0.0007(13) 0.0014(12) 0.0018(14) C14 0.0200(13) 0.0278(17) 0.0250(14) -0.0005(13) 0.0058(10) -0.0005(13) C15 0.0211(13) 0.0278(17) 0.0278(14) 0.0007(13) 0.0021(11) -0.0022(14) C16 0.0228(14) 0.0266(18) 0.0319(16) 0.0020(13) 0.0074(12) 0.0016(13) C17 0.0320(17) 0.0382(19) 0.0253(16) 0.0010(14) 0.0112(13) -0.0004(16) C18 0.0265(15) 0.038(2) 0.0228(15) -0.0018(13) 0.0037(12) -0.0053(15) C19 0.0223(14) 0.0385(19) 0.0261(14) 0.0003(14) 0.0052(11) -0.0039(15) _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 C1 1.766(3) . ? S1 C7 1.844(3) . ? Cl1 C6 1.725(4) . ? Cl2 C2 1.722(4) . ? O1 C13 1.201(4) . ? O2 N2 1.224(3) . ? O3 N2 1.213(4) . ? O4 N3 1.218(5) . ? O5 N3 1.208(5) . ? N1 C13 1.351(4) . ? N1 C12 1.467(4) . ? N2 C16 1.477(4) . ? N3 C18 1.484(4) . ? C1 C2 1.402(5) . ? C1 C6 1.407(5) . ? C2 C3 1.386(5) . ? C3 C4 1.383(7) . ? C4 C5 1.385(7) . ? C5 C6 1.378(5) . ? C7 C12 1.515(5) . ? C7 C8 1.524(4) . ? C8 C9 1.521(6) . ? C9 C10 1.516(6) . ? C10 C11 1.531(5) . ? C11 C12 1.518(5) . ? C13 C14 1.516(4) . ? C14 C15 1.378(4) . ? C14 C19 1.400(4) . ? C15 C16 1.375(4) . ? C16 C17 1.369(4) . ? C17 C18 1.376(5) . ? C18 C19 1.391(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 C1 S1 C7 102.23(16) . . ? C13 N1 C12 121.7(3) . . ? O3 N2 O2 122.8(3) . . ? O3 N2 C16 119.2(3) . . ? O2 N2 C16 118.0(3) . . ? O5 N3 O4 124.5(3) . . ? O5 N3 C18 117.4(3) . . ? O4 N3 C18 118.1(3) . . ? C2 C1 C6 117.1(3) . . ? C2 C1 S1 119.9(3) . . ? C6 C1 S1 122.9(3) . . ? C3 C2 C1 121.6(4) . . ? C3 C2 Cl2 117.0(3) . . ? C1 C2 Cl2 121.4(3) . . ? C4 C3 C2 119.4(4) . . ? C3 C4 C5 120.6(4) . . ? C6 C5 C4 119.7(4) . . ? C5 C6 C1 121.6(3) . . ? C5 C6 Cl1 118.1(3) . . ? C1 C6 Cl1 120.3(3) . . ? C12 C7 C8 110.7(3) . . ? C12 C7 S1 112.8(2) . . ? C8 C7 S1 107.7(2) . . ? C9 C8 C7 111.1(3) . . ? C10 C9 C8 111.7(3) . . ? C9 C10 C11 110.7(3) . . ? C12 C11 C10 111.4(3) . . ? N1 C12 C7 112.2(3) . . ? N1 C12 C11 111.4(3) . . ? C7 C12 C11 110.5(3) . . ? O1 C13 N1 123.1(3) . . ? O1 C13 C14 119.7(3) . . ? N1 C13 C14 117.2(3) . . ? C15 C14 C19 119.6(3) . . ? C15 C14 C13 115.6(3) . . ? C19 C14 C13 124.8(3) . . ? C16 C15 C14 119.4(3) . . ? C17 C16 C15 123.8(3) . . ? C17 C16 N2 117.3(3) . . ? C15 C16 N2 119.0(3) . . ? C16 C17 C18 115.5(3) . . ? C17 C18 C19 124.0(3) . . ? C17 C18 N3 118.0(3) . . ? C19 C18 N3 118.0(3) . . ? C18 C19 C14 117.7(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.898(19) 2.16(3) 2.988(4) 154(4) 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.371 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.075 # Attachment '- 6a.cif' data_a106 _database_code_depnum_ccdc_archive 'CCDC 806369' #TrackingRef '- 6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H31 Cl2 N O6 S2' _chemical_formula_weight 576.53 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3366(10) _cell_length_b 10.2792(11) _cell_length_c 16.2940(17) _cell_angle_alpha 105.126(2) _cell_angle_beta 101.706(2) _cell_angle_gamma 99.829(2) _cell_volume 1436.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5126 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.30 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.410 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8031 _exptl_absorpt_correction_T_max 0.9680 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 18790 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6589 _reflns_number_gt 5680 _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^)+(0.0851P)^2^+1.3339P] 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 6589 _refine_ls_number_parameters 342 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1800 _refine_ls_wR_factor_gt 0.1672 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.147 _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 C10 C 0.3437(9) -0.0628(8) 0.2254(10) 0.096(3) Uani 0.59(2) 1 d PD A 1 H10A H 0.3651 -0.1300 0.1791 0.144 Uiso 0.59(2) 1 calc PR A 1 H10B H 0.2376 -0.0677 0.2121 0.144 Uiso 0.59(2) 1 calc PR A 1 H10C H 0.3746 -0.0819 0.2801 0.144 Uiso 0.59(2) 1 calc PR A 1 C11 C 0.3869(11) 0.1032(13) 0.1419(5) 0.096(3) Uani 0.59(2) 1 d PD A 1 H11A H 0.4401 0.1934 0.1445 0.144 Uiso 0.59(2) 1 calc PR A 1 H11B H 0.2805 0.0957 0.1246 0.144 Uiso 0.59(2) 1 calc PR A 1 H11C H 0.4135 0.0335 0.0997 0.144 Uiso 0.59(2) 1 calc PR A 1 C12 C 0.4160(11) 0.1977(11) 0.3055(5) 0.096(3) Uani 0.59(2) 1 d PDU A 1 H12A H 0.4612 0.1871 0.3611 0.144 Uiso 0.59(2) 1 calc PR A 1 H12B H 0.3116 0.1963 0.3010 0.144 Uiso 0.59(2) 1 calc PR A 1 H12C H 0.4665 0.2844 0.3015 0.144 Uiso 0.59(2) 1 calc PR A 1 C10A C 0.3444(11) -0.0182(13) 0.2702(10) 0.066(3) Uani 0.41(2) 1 d PD A 2 H10D H 0.3557 -0.1100 0.2446 0.099 Uiso 0.41(2) 1 calc PR A 2 H10E H 0.2396 -0.0175 0.2566 0.099 Uiso 0.41(2) 1 calc PR A 2 H10F H 0.3841 0.0092 0.3330 0.099 Uiso 0.41(2) 1 calc PR A 2 C11A C 0.3519(12) 0.0740(13) 0.1410(4) 0.066(3) Uani 0.41(2) 1 d PD A 2 H11D H 0.4245 0.1098 0.1134 0.099 Uiso 0.41(2) 1 calc PR A 2 H11E H 0.2773 0.1277 0.1427 0.099 Uiso 0.41(2) 1 calc PR A 2 H11F H 0.3042 -0.0210 0.1079 0.099 Uiso 0.41(2) 1 calc PR A 2 C12A C 0.4498(14) 0.2321(8) 0.2953(7) 0.066(3) Uani 0.41(2) 1 d PD A 2 H12D H 0.4972 0.2375 0.3546 0.099 Uiso 0.41(2) 1 calc PR A 2 H12E H 0.3530 0.2533 0.2930 0.099 Uiso 0.41(2) 1 calc PR A 2 H12F H 0.5115 0.2975 0.2767 0.099 Uiso 0.41(2) 1 calc PR A 2 S1 S 0.86361(9) -0.02522(7) 0.16261(5) 0.03402(19) Uani 1 1 d . . . S2 S 0.98223(8) 0.27286(7) 0.47425(4) 0.02903(18) Uani 1 1 d . . . Cl1 Cl 1.00952(11) -0.14342(11) 0.31682(6) 0.0551(3) Uani 1 1 d . . . Cl2 Cl 0.55171(13) -0.21435(12) 0.03181(7) 0.0707(3) Uani 1 1 d . . . O1 O 1.0039(2) 0.2477(2) 0.16502(13) 0.0341(5) Uani 1 1 d . . . O2 O 1.0326(3) 0.4431(2) 0.27497(16) 0.0523(7) Uani 1 1 d . . . O3 O 0.5835(2) 0.0599(3) 0.24628(18) 0.0497(6) Uani 1 1 d . A . O4 O 0.6879(3) 0.2479(3) 0.21477(19) 0.0521(6) Uani 1 1 d . . . O5 O 0.8970(2) 0.1345(2) 0.45631(14) 0.0353(5) Uani 1 1 d . . . O6 O 0.9521(3) 0.3840(2) 0.53697(14) 0.0372(5) Uani 1 1 d . . . N1 N 0.9530(3) 0.3121(2) 0.38273(15) 0.0302(5) Uani 1 1 d . . . H1N H 0.974(4) 0.396(4) 0.392(2) 0.036 Uiso 1 1 d . . . C1 C 0.9759(3) 0.2242(3) 0.30213(18) 0.0278(5) Uani 1 1 d . . . H1 H 1.0659 0.1896 0.3178 0.033 Uiso 1 1 calc R . . C2 C 1.0059(3) 0.3203(3) 0.24620(19) 0.0320(6) Uani 1 1 d . . . C3 C 1.0207(4) 0.3198(3) 0.0979(2) 0.0385(7) Uani 1 1 d . . . C4 C 1.0027(6) 0.1986(5) 0.0169(3) 0.0648(11) Uani 1 1 d . . . H4A H 1.0784 0.1486 0.0286 0.097 Uiso 1 1 calc R . . H4B H 1.0135 0.2326 -0.0316 0.097 Uiso 1 1 calc R . . H4C H 0.9047 0.1380 0.0024 0.097 Uiso 1 1 calc R . . C5 C 0.8969(5) 0.3954(5) 0.0851(3) 0.0637(11) Uani 1 1 d . . . H5A H 0.8026 0.3364 0.0811 0.096 Uiso 1 1 calc R . . H5B H 0.8911 0.4202 0.0318 0.096 Uiso 1 1 calc R . . H5C H 0.9182 0.4779 0.1341 0.096 Uiso 1 1 calc R . . C6 C 1.1766(5) 0.4135(5) 0.1250(3) 0.0632(11) Uani 1 1 d . . . H6A H 1.1838 0.4924 0.1739 0.095 Uiso 1 1 calc R . . H6B H 1.1954 0.4441 0.0765 0.095 Uiso 1 1 calc R . . H6C H 1.2497 0.3635 0.1417 0.095 Uiso 1 1 calc R . . C7 C 0.8394(3) 0.0997(3) 0.25956(18) 0.0279(5) Uani 1 1 d . . . H7 H 0.8300 0.0512 0.3033 0.034 Uiso 1 1 calc R . . C8 C 0.6954(3) 0.1466(3) 0.23723(19) 0.0324(6) Uani 1 1 d . . . C9 C 0.4295(4) 0.0825(4) 0.2331(3) 0.0694(13) Uani 1 1 d D . . C13 C 0.7748(3) -0.1818(3) 0.17658(19) 0.0326(6) Uani 1 1 d . . . C14 C 0.8393(4) -0.2340(3) 0.2427(2) 0.0394(7) Uani 1 1 d . . . C15 C 0.7710(5) -0.3587(4) 0.2516(3) 0.0552(10) Uani 1 1 d . . . H15 H 0.8157 -0.3901 0.2968 0.066 Uiso 1 1 calc R . . C16 C 0.6372(6) -0.4353(4) 0.1934(3) 0.0650(12) Uani 1 1 d . . . H16 H 0.5912 -0.5190 0.1990 0.078 Uiso 1 1 calc R . . C17 C 0.5709(5) -0.3897(4) 0.1271(3) 0.0612(11) Uani 1 1 d . . . H17 H 0.4800 -0.4422 0.0877 0.073 Uiso 1 1 calc R . . C18 C 0.6395(4) -0.2648(3) 0.1187(2) 0.0447(8) Uani 1 1 d . . . C19 C 1.1739(3) 0.2741(3) 0.50768(18) 0.0320(6) Uani 1 1 d . . . C20 C 1.2152(4) 0.1538(3) 0.5139(2) 0.0411(7) Uani 1 1 d . . . H20 H 1.1426 0.0712 0.4975 0.049 Uiso 1 1 calc R . . C21 C 1.3648(4) 0.1569(4) 0.5444(3) 0.0503(8) Uani 1 1 d . . . H21 H 1.3920 0.0755 0.5487 0.060 Uiso 1 1 calc R . . C22 C 1.4762(4) 0.2783(4) 0.5688(2) 0.0492(8) Uani 1 1 d . . . C23 C 1.4317(4) 0.3972(4) 0.5624(2) 0.0493(8) Uani 1 1 d . . . H23 H 1.5044 0.4800 0.5790 0.059 Uiso 1 1 calc R . . C24 C 1.2825(4) 0.3971(3) 0.5320(2) 0.0431(7) Uani 1 1 d . . . H24 H 1.2552 0.4786 0.5280 0.052 Uiso 1 1 calc R . . C25 C 1.6400(5) 0.2817(6) 0.6032(4) 0.0788(15) Uani 1 1 d . . . H25A H 1.7018 0.3565 0.5920 0.118 Uiso 1 1 calc R . . H25B H 1.6604 0.1955 0.5740 0.118 Uiso 1 1 calc R . . H25C H 1.6622 0.2952 0.6654 0.118 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 C10 0.035(3) 0.161(6) 0.100(5) 0.057(4) 0.019(3) 0.014(3) C11 0.035(3) 0.161(6) 0.100(5) 0.057(4) 0.019(3) 0.014(3) C12 0.035(3) 0.161(6) 0.100(5) 0.057(4) 0.019(3) 0.014(3) C10A 0.040(4) 0.077(5) 0.096(6) 0.042(4) 0.032(3) 0.015(3) C11A 0.040(4) 0.077(5) 0.096(6) 0.042(4) 0.032(3) 0.015(3) C12A 0.040(4) 0.077(5) 0.096(6) 0.042(4) 0.032(3) 0.015(3) S1 0.0447(4) 0.0256(3) 0.0293(4) 0.0040(3) 0.0144(3) 0.0027(3) S2 0.0390(4) 0.0209(3) 0.0262(3) 0.0070(2) 0.0093(3) 0.0040(3) Cl1 0.0518(5) 0.0643(6) 0.0511(5) 0.0202(4) 0.0061(4) 0.0234(4) Cl2 0.0702(7) 0.0663(7) 0.0511(6) 0.0102(5) -0.0131(5) -0.0014(5) O1 0.0426(12) 0.0287(10) 0.0322(10) 0.0111(8) 0.0137(9) 0.0046(8) O2 0.0846(19) 0.0299(12) 0.0405(13) 0.0094(10) 0.0246(13) 0.0010(11) O3 0.0249(10) 0.0639(16) 0.0701(16) 0.0431(14) 0.0086(10) 0.0051(10) O4 0.0413(13) 0.0496(14) 0.0794(18) 0.0374(14) 0.0174(12) 0.0178(11) O5 0.0413(11) 0.0245(10) 0.0362(11) 0.0107(8) 0.0069(9) -0.0005(8) O6 0.0536(13) 0.0276(10) 0.0327(11) 0.0079(8) 0.0189(9) 0.0078(9) N1 0.0434(14) 0.0205(11) 0.0269(11) 0.0064(9) 0.0100(10) 0.0087(10) C1 0.0298(13) 0.0246(13) 0.0284(13) 0.0076(10) 0.0080(10) 0.0054(10) C2 0.0323(14) 0.0319(15) 0.0317(14) 0.0123(12) 0.0098(11) 0.0018(11) C3 0.0447(17) 0.0430(17) 0.0318(15) 0.0164(13) 0.0144(13) 0.0079(14) C4 0.096(3) 0.064(3) 0.0381(19) 0.0143(18) 0.025(2) 0.022(2) C5 0.069(3) 0.087(3) 0.063(2) 0.047(2) 0.028(2) 0.039(2) C6 0.057(2) 0.076(3) 0.062(2) 0.039(2) 0.0229(19) -0.005(2) C7 0.0288(13) 0.0260(13) 0.0281(13) 0.0075(10) 0.0090(11) 0.0035(10) C8 0.0313(14) 0.0338(15) 0.0330(14) 0.0134(12) 0.0072(11) 0.0065(11) C9 0.0276(17) 0.098(3) 0.097(3) 0.057(3) 0.0147(19) 0.0116(19) C13 0.0418(16) 0.0247(13) 0.0325(14) 0.0054(11) 0.0166(12) 0.0078(11) C14 0.0493(18) 0.0353(16) 0.0402(16) 0.0109(13) 0.0213(14) 0.0170(14) C15 0.091(3) 0.0380(18) 0.056(2) 0.0240(17) 0.038(2) 0.0271(19) C16 0.087(3) 0.0340(19) 0.077(3) 0.0165(19) 0.039(3) 0.0022(19) C17 0.061(2) 0.0375(19) 0.071(3) 0.0015(18) 0.021(2) -0.0098(17) C18 0.0484(19) 0.0356(16) 0.0421(17) 0.0040(14) 0.0105(15) 0.0023(14) C19 0.0377(15) 0.0297(14) 0.0261(13) 0.0095(11) 0.0063(11) 0.0027(11) C20 0.0434(17) 0.0290(15) 0.0472(18) 0.0137(13) 0.0060(14) 0.0025(13) C21 0.0469(19) 0.0429(19) 0.063(2) 0.0229(17) 0.0089(17) 0.0120(15) C22 0.0418(18) 0.059(2) 0.0487(19) 0.0246(17) 0.0091(15) 0.0059(16) C23 0.0437(18) 0.0439(19) 0.054(2) 0.0192(16) 0.0088(16) -0.0074(15) C24 0.0469(18) 0.0291(15) 0.0505(19) 0.0154(14) 0.0101(15) -0.0002(13) C25 0.042(2) 0.085(3) 0.111(4) 0.048(3) 0.008(2) 0.006(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 C10 C9 1.530(5) . ? C11 C9 1.538(5) . ? C12 C9 1.481(5) . ? C10A C9 1.520(5) . ? C11A C9 1.502(5) . ? C12A C9 1.561(5) . ? S1 C13 1.773(3) . ? S1 C7 1.839(3) . ? S2 O5 1.430(2) . ? S2 O6 1.430(2) . ? S2 N1 1.627(2) . ? S2 C19 1.759(3) . ? Cl1 C14 1.726(4) . ? Cl2 C18 1.732(4) . ? O1 C2 1.333(3) . ? O1 C3 1.491(3) . ? O2 C2 1.188(4) . ? O3 C8 1.312(3) . ? O3 C9 1.478(4) . ? O4 C8 1.198(4) . ? N1 C1 1.465(3) . ? C1 C2 1.537(4) . ? C1 C7 1.538(4) . ? C3 C5 1.510(5) . ? C3 C6 1.510(5) . ? C3 C4 1.517(5) . ? C7 C8 1.512(4) . ? C13 C18 1.393(4) . ? C13 C14 1.400(4) . ? C14 C15 1.388(5) . ? C15 C16 1.369(6) . ? C16 C17 1.364(7) . ? C17 C18 1.388(5) . ? C19 C20 1.378(4) . ? C19 C24 1.387(4) . ? C20 C21 1.376(5) . ? C21 C22 1.388(5) . ? C22 C23 1.379(5) . ? C22 C25 1.509(5) . ? C23 C24 1.380(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 C13 S1 C7 99.48(12) . . ? O5 S2 O6 119.20(13) . . ? O5 S2 N1 107.82(13) . . ? O6 S2 N1 105.10(12) . . ? O5 S2 C19 107.80(13) . . ? O6 S2 C19 108.21(14) . . ? N1 S2 C19 108.30(13) . . ? C2 O1 C3 120.0(2) . . ? C8 O3 C9 121.9(3) . . ? C1 N1 S2 121.84(19) . . ? N1 C1 C2 105.7(2) . . ? N1 C1 C7 109.0(2) . . ? C2 C1 C7 115.9(2) . . ? O2 C2 O1 126.2(3) . . ? O2 C2 C1 122.7(3) . . ? O1 C2 C1 111.1(2) . . ? O1 C3 C5 109.8(3) . . ? O1 C3 C6 109.4(3) . . ? C5 C3 C6 113.3(3) . . ? O1 C3 C4 101.6(3) . . ? C5 C3 C4 111.5(3) . . ? C6 C3 C4 110.7(3) . . ? C8 C7 C1 111.2(2) . . ? C8 C7 S1 111.07(19) . . ? C1 C7 S1 112.54(18) . . ? O4 C8 O3 126.5(3) . . ? O4 C8 C7 124.0(3) . . ? O3 C8 C7 109.5(2) . . ? O3 C9 C12 112.4(5) . . ? O3 C9 C11A 115.8(5) . . ? C12 C9 C11A 117.1(8) . . ? O3 C9 C10A 105.4(5) . . ? C12 C9 C10A 88.4(5) . . ? C11A C9 C10A 114.0(5) . . ? O3 C9 C10 98.9(4) . . ? C12 C9 C10 116.2(4) . . ? C11A C9 C10 93.7(6) . . ? C10A C9 C10 28.6(5) . . ? O3 C9 C11 106.9(4) . . ? C12 C9 C11 113.7(5) . . ? C11A C9 C11 15.0(5) . . ? C10A C9 C11 129.0(6) . . ? C10 C9 C11 107.5(4) . . ? O3 C9 C12A 104.2(5) . . ? C12 C9 C12A 19.3(4) . . ? C11A C9 C12A 109.1(5) . . ? C10A C9 C12A 107.6(4) . . ? C10 C9 C12A 135.5(5) . . ? C11 C9 C12A 101.5(7) . . ? C18 C13 C14 115.8(3) . . ? C18 C13 S1 121.5(2) . . ? C14 C13 S1 122.6(2) . . ? C15 C14 C13 122.2(3) . . ? C15 C14 Cl1 117.5(3) . . ? C13 C14 Cl1 120.3(2) . . ? C16 C15 C14 119.5(4) . . ? C17 C16 C15 120.5(3) . . ? C16 C17 C18 119.7(4) . . ? C17 C18 C13 122.3(4) . . ? C17 C18 Cl2 117.5(3) . . ? C13 C18 Cl2 120.2(3) . . ? C20 C19 C24 120.1(3) . . ? C20 C19 S2 119.7(2) . . ? C24 C19 S2 120.1(2) . . ? C21 C20 C19 119.5(3) . . ? C20 C21 C22 121.7(3) . . ? C23 C22 C21 117.6(3) . . ? C23 C22 C25 120.8(4) . . ? C21 C22 C25 121.6(4) . . ? C22 C23 C24 121.9(3) . . ? C23 C24 C19 119.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O6 0.81(4) 2.17(4) 2.951(3) 160(3) 2_766 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.707 _refine_diff_density_min -0.671 _refine_diff_density_rms 0.091