# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'I Coldham' _publ_contact_author_name 'I Coldham' _publ_contact_author_email I.COLDHAM@SHEFFIELD.AC.UK _publ_section_title ; Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (+-)-crispine A ; # Attachment 'Coldham_B822743H_27a.cif' data_lw1x_0m _database_code_depnum_ccdc_archive 'CCDC 714109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 N2 O4' _chemical_formula_weight 384.46 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8538(5) _cell_length_b 10.2423(4) _cell_length_c 18.5130(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.106(2) _cell_angle_gamma 90.00 _cell_volume 2026.12(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5012 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 29.73 _exptl_crystal_description BLOCK _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16441 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4645 _reflns_number_gt 3200 _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^)+(0.0645P)^2^+0.3778P] 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 4645 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.60550(11) 0.59975(13) 0.32845(6) 0.0419(3) Uani 1 1 d . . . N2 N 0.66263(12) 0.65080(13) 0.14631(6) 0.0420(3) Uani 1 1 d . . . O1 O 0.41245(10) 0.50673(12) 0.29208(6) 0.0547(3) Uani 1 1 d . . . O2 O 0.81061(11) 0.66235(14) 0.33716(6) 0.0634(4) Uani 1 1 d . . . O3 O 0.90995(12) 0.74760(13) 0.19121(7) 0.0615(3) Uani 1 1 d . . . O4 O 0.97816(10) 0.54805(13) 0.22891(7) 0.0602(3) Uani 1 1 d . . . C1 C 0.51565(14) 0.52982(15) 0.28007(8) 0.0412(3) Uani 1 1 d . . . C2 C 0.57518(14) 0.48729(15) 0.21559(8) 0.0406(3) Uani 1 1 d . . . H2 H 0.5572 0.3927 0.2051 0.049 Uiso 1 1 calc R . . C3 C 0.71576(14) 0.50612(15) 0.24362(8) 0.0405(3) Uani 1 1 d . . . H3 H 0.7580 0.4214 0.2592 0.049 Uiso 1 1 calc R . . C4 C 0.72204(14) 0.59957(16) 0.30759(8) 0.0428(4) Uani 1 1 d . . . C5 C 0.55087(14) 0.56640(15) 0.14218(8) 0.0404(3) Uani 1 1 d . . . H5 H 0.5571 0.5014 0.1027 0.048 Uiso 1 1 calc R . . C6 C 0.42309(15) 0.63449(16) 0.11872(8) 0.0453(4) Uani 1 1 d . . . C7 C 0.40974(18) 0.68569(19) 0.03896(9) 0.0584(5) Uani 1 1 d . . . H7A H 0.4447 0.6184 0.0099 0.070 Uiso 1 1 calc R . . H7B H 0.3192 0.6923 0.0189 0.070 Uiso 1 1 calc R . . C8 C 0.4696(2) 0.8155(2) 0.02530(11) 0.0733(6) Uani 1 1 d . . . H8A H 0.4536 0.8321 -0.0282 0.088 Uiso 1 1 calc R . . H8B H 0.4269 0.8852 0.0486 0.088 Uiso 1 1 calc R . . C9 C 0.6083(2) 0.8271(2) 0.05270(12) 0.0836(7) Uani 1 1 d . . . H9A H 0.6208 0.8859 0.0958 0.100 Uiso 1 1 calc R . . H9B H 0.6460 0.8704 0.0140 0.100 Uiso 1 1 calc R . . C10 C 0.68096(19) 0.7022(2) 0.07438(9) 0.0654(5) Uani 1 1 d . . . H10A H 0.6545 0.6351 0.0364 0.079 Uiso 1 1 calc R . . H10B H 0.7712 0.7192 0.0760 0.079 Uiso 1 1 calc R . . C11 C 0.76590(14) 0.56612(15) 0.17932(8) 0.0414(4) Uani 1 1 d . . . H11 H 0.7757 0.4952 0.1436 0.050 Uiso 1 1 calc R . . C12 C 0.89044(15) 0.63461(17) 0.20075(8) 0.0452(4) Uani 1 1 d . . . C13 C 1.10464(17) 0.5968(3) 0.25355(12) 0.0742(6) Uani 1 1 d . . . H13A H 1.1192 0.6733 0.2235 0.089 Uiso 1 1 calc R . . H13B H 1.1656 0.5282 0.2463 0.089 Uiso 1 1 calc R . . C14 C 1.12552(19) 0.6350(2) 0.33191(12) 0.0728(6) Uani 1 1 d . . . H14A H 1.0694 0.7072 0.3387 0.109 Uiso 1 1 calc R . . H14B H 1.2126 0.6628 0.3472 0.109 Uiso 1 1 calc R . . H14C H 1.1084 0.5603 0.3617 0.109 Uiso 1 1 calc R . . C15 C 0.32180(16) 0.52869(19) 0.11719(10) 0.0575(5) Uani 1 1 d . . . H15A H 0.3269 0.4914 0.1664 0.086 Uiso 1 1 calc R . . H15B H 0.3351 0.4597 0.0827 0.086 Uiso 1 1 calc R . . H15C H 0.2390 0.5677 0.1015 0.086 Uiso 1 1 calc R . . C16 C 0.40044(17) 0.74578(17) 0.17021(9) 0.0538(4) Uani 1 1 d . . . H16A H 0.3861 0.7093 0.2170 0.081 Uiso 1 1 calc R . . H16B H 0.3269 0.7961 0.1476 0.081 Uiso 1 1 calc R . . H16C H 0.4738 0.8031 0.1789 0.081 Uiso 1 1 calc R . . C17 C 0.57942(14) 0.65946(16) 0.39437(8) 0.0445(4) Uani 1 1 d . . . C18 C 0.61665(19) 0.5973(2) 0.46038(10) 0.0635(5) Uani 1 1 d . . . H18 H 0.6613 0.5173 0.4624 0.076 Uiso 1 1 calc R . . C19 C 0.5886(2) 0.6521(3) 0.52376(11) 0.0839(8) Uani 1 1 d . . . H19 H 0.6146 0.6102 0.5697 0.101 Uiso 1 1 calc R . . C20 C 0.5239(2) 0.7658(3) 0.52019(13) 0.0953(9) Uani 1 1 d . . . H20 H 0.5035 0.8024 0.5637 0.114 Uiso 1 1 calc R . . C21 C 0.4877(2) 0.8286(3) 0.45450(15) 0.1032(10) Uani 1 1 d . . . H21 H 0.4431 0.9086 0.4528 0.124 Uiso 1 1 calc R . . C22 C 0.5161(2) 0.7753(2) 0.39055(11) 0.0733(6) Uani 1 1 d . . . H22 H 0.4920 0.8186 0.3449 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 N1 0.0389(7) 0.0503(8) 0.0380(6) -0.0030(6) 0.0110(5) -0.0021(6) N2 0.0425(7) 0.0498(7) 0.0344(6) -0.0007(5) 0.0089(5) -0.0046(6) O1 0.0400(6) 0.0699(8) 0.0564(7) 0.0005(6) 0.0147(5) -0.0070(6) O2 0.0451(7) 0.0986(10) 0.0477(7) -0.0208(6) 0.0113(5) -0.0182(7) O3 0.0648(8) 0.0587(8) 0.0613(8) -0.0062(6) 0.0118(6) -0.0182(6) O4 0.0383(6) 0.0688(8) 0.0743(8) -0.0117(7) 0.0119(6) 0.0015(6) C1 0.0383(8) 0.0427(8) 0.0431(8) 0.0037(7) 0.0086(6) -0.0001(6) C2 0.0407(8) 0.0373(8) 0.0445(8) -0.0048(6) 0.0097(6) -0.0025(6) C3 0.0383(8) 0.0401(8) 0.0442(8) -0.0010(6) 0.0102(6) 0.0021(6) C4 0.0385(8) 0.0538(9) 0.0362(7) 0.0022(7) 0.0073(6) -0.0008(7) C5 0.0444(9) 0.0411(8) 0.0357(7) -0.0092(6) 0.0073(6) -0.0033(6) C6 0.0449(9) 0.0500(9) 0.0388(8) -0.0070(7) 0.0017(6) -0.0007(7) C7 0.0599(11) 0.0700(12) 0.0412(9) -0.0028(8) -0.0027(7) 0.0041(9) C8 0.0913(16) 0.0743(14) 0.0519(11) 0.0118(10) 0.0060(10) 0.0014(12) C9 0.1047(18) 0.0772(15) 0.0590(12) 0.0273(11) -0.0131(11) -0.0279(13) C10 0.0605(11) 0.0946(15) 0.0419(9) 0.0089(9) 0.0107(8) -0.0170(11) C11 0.0412(8) 0.0448(8) 0.0405(8) -0.0116(6) 0.0134(6) -0.0021(7) C12 0.0450(9) 0.0545(10) 0.0395(8) -0.0121(7) 0.0171(7) -0.0047(8) C13 0.0351(9) 0.1079(17) 0.0809(14) -0.0093(12) 0.0135(9) -0.0035(10) C14 0.0557(12) 0.0770(14) 0.0812(14) -0.0097(11) -0.0006(10) -0.0001(10) C15 0.0448(10) 0.0684(12) 0.0565(10) -0.0125(9) 0.0012(7) -0.0066(8) C16 0.0565(10) 0.0528(10) 0.0509(9) -0.0063(8) 0.0060(8) 0.0101(8) C17 0.0387(8) 0.0587(10) 0.0379(8) -0.0051(7) 0.0116(6) -0.0045(7) C18 0.0693(12) 0.0748(13) 0.0459(10) 0.0057(9) 0.0087(8) -0.0091(10) C19 0.0823(16) 0.131(2) 0.0405(10) -0.0058(12) 0.0169(10) -0.0372(16) C20 0.0580(13) 0.170(3) 0.0629(14) -0.0515(17) 0.0255(11) -0.0200(16) C21 0.0859(18) 0.129(2) 0.0919(19) -0.0533(17) 0.0076(14) 0.0342(16) C22 0.0797(14) 0.0814(14) 0.0563(11) -0.0134(10) 0.0048(10) 0.0239(12) _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 C4 1.3859(19) . ? N1 C1 1.400(2) . ? N1 C17 1.4368(19) . ? N2 C11 1.463(2) . ? N2 C10 1.478(2) . ? N2 C5 1.4805(19) . ? O1 C1 1.2031(18) . ? O2 C4 1.2053(19) . ? O3 C12 1.195(2) . ? O4 C12 1.338(2) . ? O4 C13 1.457(2) . ? C1 C2 1.518(2) . ? C2 C3 1.535(2) . ? C2 C5 1.564(2) . ? C2 H2 1.0000 . ? C3 C4 1.515(2) . ? C3 C11 1.523(2) . ? C3 H3 1.0000 . ? C5 C6 1.545(2) . ? C5 H5 1.0000 . ? C6 C16 1.533(2) . ? C6 C15 1.540(2) . ? C6 C7 1.550(2) . ? C7 C8 1.520(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.507(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.519(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.513(2) . ? C11 H11 1.0000 . ? C13 C14 1.481(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.367(3) . ? C17 C18 1.374(2) . ? C18 C19 1.382(3) . ? C18 H18 0.9500 . ? C19 C20 1.355(4) . ? C19 H19 0.9500 . ? C20 C21 1.371(4) . ? C20 H20 0.9500 . ? C21 C22 1.387(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C4 N1 C1 112.86(12) . . ? C4 N1 C17 124.25(13) . . ? C1 N1 C17 122.83(12) . . ? C11 N2 C10 111.91(13) . . ? C11 N2 C5 103.65(11) . . ? C10 N2 C5 113.59(12) . . ? C12 O4 C13 117.52(16) . . ? O1 C1 N1 123.30(14) . . ? O1 C1 C2 128.88(14) . . ? N1 C1 C2 107.77(12) . . ? C1 C2 C3 103.49(12) . . ? C1 C2 C5 120.30(13) . . ? C3 C2 C5 103.57(11) . . ? C1 C2 H2 109.6 . . ? C3 C2 H2 109.6 . . ? C5 C2 H2 109.6 . . ? C4 C3 C11 112.52(13) . . ? C4 C3 C2 104.43(11) . . ? C11 C3 C2 104.89(12) . . ? C4 C3 H3 111.5 . . ? C11 C3 H3 111.5 . . ? C2 C3 H3 111.5 . . ? O2 C4 N1 124.54(14) . . ? O2 C4 C3 127.95(14) . . ? N1 C4 C3 107.50(13) . . ? N2 C5 C6 115.97(12) . . ? N2 C5 C2 104.23(11) . . ? C6 C5 C2 118.97(12) . . ? N2 C5 H5 105.5 . . ? C6 C5 H5 105.5 . . ? C2 C5 H5 105.5 . . ? C16 C6 C15 110.04(14) . . ? C16 C6 C5 113.25(12) . . ? C15 C6 C5 106.87(13) . . ? C16 C6 C7 110.02(14) . . ? C15 C6 C7 105.87(13) . . ? C5 C6 C7 110.48(13) . . ? C8 C7 C6 118.90(15) . . ? C8 C7 H7A 107.6 . . ? C6 C7 H7A 107.6 . . ? C8 C7 H7B 107.6 . . ? C6 C7 H7B 107.6 . . ? H7A C7 H7B 107.0 . . ? C9 C8 C7 116.38(18) . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 117.62(18) . . ? C8 C9 H9A 107.9 . . ? C10 C9 H9A 107.9 . . ? C8 C9 H9B 107.9 . . ? C10 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? N2 C10 C9 113.11(17) . . ? N2 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? N2 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N2 C11 C12 114.73(13) . . ? N2 C11 C3 102.30(11) . . ? C12 C11 C3 114.06(12) . . ? N2 C11 H11 108.5 . . ? C12 C11 H11 108.5 . . ? C3 C11 H11 108.5 . . ? O3 C12 O4 124.53(15) . . ? O3 C12 C11 125.70(16) . . ? O4 C12 C11 109.69(14) . . ? O4 C13 C14 111.78(16) . . ? O4 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? O4 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? 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 . . ? C6 C15 H15A 109.5 . . ? C6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C16 H16A 109.5 . . ? C6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 120.98(17) . . ? C22 C17 N1 119.85(15) . . ? C18 C17 N1 119.16(16) . . ? C17 C18 C19 119.5(2) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 119.8(2) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.8(2) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C20 C21 C22 120.0(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 118.9(2) . . ? C17 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.157 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.054 # Attachment 'Coldham_B822743H_32.cif' data_oic82p21c _database_code_depnum_ccdc_archive 'CCDC 714110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N O6' _chemical_formula_weight 361.38 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 P2(1)/c 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 11.8340(4) _cell_length_b 16.5803(5) _cell_length_c 9.4455(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.5560(10) _cell_angle_gamma 90.00 _cell_volume 1735.31(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9934 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 31.86 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9619 _exptl_absorpt_correction_T_max 0.9877 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 29528 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3991 _reflns_number_gt 3541 _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^)+(0.0524P)^2^+0.6411P] 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 3991 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.38621(8) 0.65086(5) 0.95504(10) 0.01405(19) Uani 1 1 d . . . O1 O 0.65906(8) 0.73232(5) 0.99793(10) 0.0255(2) Uani 1 1 d . . . O2 O 0.63916(7) 0.63287(5) 1.14927(9) 0.02130(19) Uani 1 1 d . . . O3 O 0.61558(8) 0.59396(5) 0.71327(10) 0.02215(19) Uani 1 1 d . . . O4 O 0.46466(7) 0.64193(5) 0.51038(9) 0.01853(18) Uani 1 1 d . . . O5 O 0.31696(8) 0.53060(5) 0.66129(9) 0.02019(18) Uani 1 1 d . . . O6 O 0.18784(8) 0.60332(5) 0.47341(9) 0.02206(19) Uani 1 1 d . . . C1 C 0.29065(10) 0.69063(6) 0.82788(12) 0.0144(2) Uani 1 1 d . . . H1 H 0.3006 0.7499 0.8478 0.017 Uiso 1 1 calc R . . C2 C 0.16286(10) 0.67037(7) 0.81732(12) 0.0166(2) Uani 1 1 d . . . C3 C 0.06605(11) 0.70199(7) 0.69729(13) 0.0213(2) Uani 1 1 d . . . H3 H 0.0814 0.7329 0.6214 0.026 Uiso 1 1 calc R . . C4 C -0.05227(11) 0.68861(8) 0.68791(15) 0.0256(3) Uani 1 1 d . . . H4 H -0.1173 0.7100 0.6055 0.031 Uiso 1 1 calc R . . C5 C -0.07548(11) 0.64395(8) 0.79931(16) 0.0262(3) Uani 1 1 d . . . H5 H -0.1562 0.6353 0.7942 0.031 Uiso 1 1 calc R . . C6 C 0.01989(11) 0.61212(7) 0.91777(15) 0.0233(3) Uani 1 1 d . . . H6 H 0.0038 0.5811 0.9932 0.028 Uiso 1 1 calc R . . C7 C 0.13972(10) 0.62475(7) 0.92852(13) 0.0184(2) Uani 1 1 d . . . C8 C 0.24319(11) 0.58928(7) 1.05709(13) 0.0197(2) Uani 1 1 d . . . H8A H 0.2177 0.5376 1.0892 0.024 Uiso 1 1 calc R . . H8B H 0.2663 0.6266 1.1444 0.024 Uiso 1 1 calc R . . C9 C 0.35072(10) 0.57489(6) 1.00847(12) 0.0162(2) Uani 1 1 d . . . H9A H 0.4191 0.5537 1.0948 0.019 Uiso 1 1 calc R . . H9B H 0.3297 0.5343 0.9264 0.019 Uiso 1 1 calc R . . C10 C 0.49162(10) 0.63870(6) 0.90720(12) 0.0142(2) Uani 1 1 d . . . H10 H 0.5044 0.5795 0.8999 0.017 Uiso 1 1 calc R . . C11 C 0.45991(10) 0.67578(6) 0.74961(12) 0.0147(2) Uani 1 1 d . . . H11 H 0.4876 0.7332 0.7618 0.018 Uiso 1 1 calc R . . C12 C 0.32096(10) 0.67529(6) 0.68225(12) 0.0148(2) Uani 1 1 d . . . H12 H 0.2905 0.7205 0.6085 0.018 Uiso 1 1 calc R . . C13 C 0.60567(10) 0.67497(7) 1.02060(12) 0.0161(2) Uani 1 1 d . . . C14 C 0.75212(11) 0.65707(8) 1.26640(13) 0.0232(3) Uani 1 1 d . . . H14A H 0.7508 0.6413 1.3669 0.028 Uiso 1 1 calc R . . H14B H 0.7607 0.7164 1.2652 0.028 Uiso 1 1 calc R . . C15 C 0.52361(10) 0.63231(6) 0.65889(12) 0.0158(2) Uani 1 1 d . . . C16 C 0.51545(12) 0.60114(7) 0.41110(13) 0.0227(3) Uani 1 1 d . . . H16A H 0.6033 0.5976 0.4603 0.034 Uiso 1 1 calc R . . H16B H 0.4961 0.6315 0.3165 0.034 Uiso 1 1 calc R . . H16C H 0.4814 0.5467 0.3892 0.034 Uiso 1 1 calc R . . C17 C 0.27619(10) 0.59502(7) 0.60807(12) 0.0159(2) Uani 1 1 d . . . C18 C 0.14811(12) 0.52828(8) 0.39291(15) 0.0272(3) Uani 1 1 d . . . H18A H 0.2176 0.5000 0.3830 0.041 Uiso 1 1 calc R . . H18B H 0.0893 0.5397 0.2922 0.041 Uiso 1 1 calc R . . H18C H 0.1105 0.4944 0.4491 0.041 Uiso 1 1 calc R . . C19 C 0.85771(11) 0.61770(8) 1.24049(16) 0.0280(3) Uani 1 1 d . . . H19A H 0.8494 0.5589 1.2426 0.042 Uiso 1 1 calc R . . H19B H 0.9327 0.6343 1.3201 0.042 Uiso 1 1 calc R . . H19C H 0.8598 0.6342 1.1418 0.042 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 N1 0.0126(4) 0.0156(4) 0.0141(4) 0.0010(3) 0.0048(3) 0.0013(3) O1 0.0210(4) 0.0228(4) 0.0271(5) 0.0048(3) 0.0015(4) -0.0062(3) O2 0.0156(4) 0.0306(5) 0.0147(4) 0.0028(3) 0.0015(3) -0.0054(3) O3 0.0184(4) 0.0268(4) 0.0222(4) 0.0012(3) 0.0084(3) 0.0052(3) O4 0.0209(4) 0.0218(4) 0.0147(4) 0.0001(3) 0.0085(3) 0.0031(3) O5 0.0245(4) 0.0168(4) 0.0179(4) -0.0010(3) 0.0057(3) 0.0000(3) O6 0.0196(4) 0.0241(4) 0.0173(4) -0.0051(3) 0.0000(3) 0.0031(3) C1 0.0148(5) 0.0141(5) 0.0138(5) -0.0007(4) 0.0043(4) 0.0012(4) C2 0.0152(5) 0.0159(5) 0.0181(5) -0.0053(4) 0.0053(4) 0.0007(4) C3 0.0195(6) 0.0222(6) 0.0207(6) -0.0028(4) 0.0049(5) 0.0037(4) C4 0.0166(6) 0.0273(6) 0.0279(6) -0.0078(5) 0.0016(5) 0.0043(5) C5 0.0162(6) 0.0257(6) 0.0368(7) -0.0110(5) 0.0096(5) -0.0027(5) C6 0.0214(6) 0.0221(6) 0.0298(6) -0.0059(5) 0.0131(5) -0.0038(4) C7 0.0177(5) 0.0176(5) 0.0212(6) -0.0056(4) 0.0083(4) -0.0010(4) C8 0.0204(6) 0.0215(5) 0.0193(5) 0.0009(4) 0.0097(5) -0.0012(4) C9 0.0169(5) 0.0160(5) 0.0159(5) 0.0009(4) 0.0060(4) 0.0000(4) C10 0.0142(5) 0.0147(5) 0.0140(5) -0.0004(4) 0.0053(4) 0.0005(4) C11 0.0152(5) 0.0147(5) 0.0143(5) -0.0003(4) 0.0053(4) -0.0003(4) C12 0.0148(5) 0.0156(5) 0.0137(5) 0.0005(4) 0.0045(4) 0.0020(4) C13 0.0149(5) 0.0173(5) 0.0168(5) -0.0009(4) 0.0064(4) 0.0022(4) C14 0.0158(5) 0.0351(7) 0.0152(5) -0.0009(5) 0.0010(4) -0.0055(5) C15 0.0162(5) 0.0160(5) 0.0167(5) -0.0001(4) 0.0076(4) -0.0023(4) C16 0.0301(6) 0.0238(6) 0.0185(6) -0.0011(4) 0.0140(5) 0.0034(5) C17 0.0146(5) 0.0201(5) 0.0143(5) -0.0016(4) 0.0066(4) 0.0005(4) C18 0.0228(6) 0.0299(6) 0.0234(6) -0.0108(5) 0.0013(5) -0.0005(5) C19 0.0181(6) 0.0287(6) 0.0334(7) 0.0010(5) 0.0042(5) -0.0010(5) _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 C9 1.4719(14) . ? N1 C10 1.4821(13) . ? N1 C1 1.4840(13) . ? O1 C13 1.2018(14) . ? O2 C13 1.3353(14) . ? O2 C14 1.4606(14) . ? O3 C15 1.2085(14) . ? O4 C15 1.3389(14) . ? O4 C16 1.4471(14) . ? O5 C17 1.2065(14) . ? O6 C17 1.3401(14) . ? O6 C18 1.4479(14) . ? C1 C2 1.5178(15) . ? C1 C12 1.5596(14) . ? C1 H1 1.0000 . ? C2 C7 1.3972(16) . ? C2 C3 1.4002(16) . ? C3 C4 1.3893(17) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.3848(19) . ? C5 H5 0.9500 . ? C6 C7 1.4014(16) . ? C6 H6 0.9500 . ? C7 C8 1.5086(16) . ? C8 C9 1.5157(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C13 1.5216(15) . ? C10 C11 1.5305(14) . ? C10 H10 1.0000 . ? C11 C15 1.5085(15) . ? C11 C12 1.5407(15) . ? C11 H11 1.0000 . ? C12 C17 1.5108(15) . ? C12 H12 1.0000 . ? C14 C19 1.5041(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C10 111.11(8) . . ? C9 N1 C1 115.44(8) . . ? C10 N1 C1 107.30(8) . . ? C13 O2 C14 116.49(9) . . ? C15 O4 C16 116.17(9) . . ? C17 O6 C18 114.29(9) . . ? N1 C1 C2 114.42(9) . . ? N1 C1 C12 107.19(8) . . ? C2 C1 C12 116.00(9) . . ? N1 C1 H1 106.2 . . ? C2 C1 H1 106.2 . . ? C12 C1 H1 106.2 . . ? C7 C2 C3 119.39(10) . . ? C7 C2 C1 121.61(10) . . ? C3 C2 C1 118.91(10) . . ? C4 C3 C2 120.77(12) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.94(12) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.53(11) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 121.23(12) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 119.14(11) . . ? C2 C7 C8 119.88(10) . . ? C6 C7 C8 120.98(11) . . ? C7 C8 C9 110.36(9) . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N1 C9 C8 109.89(9) . . ? N1 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? N1 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N1 C10 C13 111.41(8) . . ? N1 C10 C11 107.26(8) . . ? C13 C10 C11 112.32(9) . . ? N1 C10 H10 108.6 . . ? C13 C10 H10 108.6 . . ? C11 C10 H10 108.6 . . ? C15 C11 C10 111.09(9) . . ? C15 C11 C12 115.89(9) . . ? C10 C11 C12 105.14(8) . . ? C15 C11 H11 108.2 . . ? C10 C11 H11 108.2 . . ? C12 C11 H11 108.2 . . ? C17 C12 C11 110.23(9) . . ? C17 C12 C1 113.64(9) . . ? C11 C12 C1 100.23(8) . . ? C17 C12 H12 110.8 . . ? C11 C12 H12 110.8 . . ? C1 C12 H12 110.8 . . ? O1 C13 O2 124.69(10) . . ? O1 C13 C10 125.39(10) . . ? O2 C13 C10 109.91(9) . . ? O2 C14 C19 110.43(10) . . ? O2 C14 H14A 109.6 . . ? C19 C14 H14A 109.6 . . ? O2 C14 H14B 109.6 . . ? C19 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? O3 C15 O4 124.63(10) . . ? O3 C15 C11 124.41(10) . . ? O4 C15 C11 110.96(9) . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 O6 123.44(10) . . ? O5 C17 C12 124.25(10) . . ? O6 C17 C12 112.29(9) . . ? O6 C18 H18A 109.5 . . ? O6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.483 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051 # Attachment 'Coldham_B822743H_38a.cif' data_sj223_0m _database_code_depnum_ccdc_archive 'CCDC 714111' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H28 Cl3 N O6 S2' _chemical_formula_weight 632.97 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 9.0677(3) _cell_length_b 12.2382(4) _cell_length_c 13.3377(4) _cell_angle_alpha 88.777(2) _cell_angle_beta 73.519(2) _cell_angle_gamma 80.784(2) _cell_volume 1400.53(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9812 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 22.21 _exptl_crystal_description NEEDLE _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8513 _exptl_absorpt_correction_T_max 0.9402 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17709 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6433 _reflns_number_gt 5686 _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^)+(0.0376P)^2^+0.7191P] 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 6433 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.03154(4) 0.71645(3) 0.88235(2) 0.01390(8) Uani 1 1 d . . . S2 S 0.26039(4) 0.96276(3) 0.73521(3) 0.01467(8) Uani 1 1 d . . . N1 N -0.02524(14) 0.80478(10) 0.65214(8) 0.0135(2) Uani 1 1 d . . . O1 O 0.04671(13) 0.78500(9) 0.96462(7) 0.0192(2) Uani 1 1 d . . . O2 O -0.12180(12) 0.70334(9) 0.87874(8) 0.0198(2) Uani 1 1 d . . . O3 O 0.37773(12) 0.90766(9) 0.64642(8) 0.0207(2) Uani 1 1 d . . . O4 O 0.21048(13) 1.08083(9) 0.73306(8) 0.0214(2) Uani 1 1 d . . . O5 O -0.27559(12) 1.28962(8) 0.76839(8) 0.0181(2) Uani 1 1 d . . . O6 O -0.46056(12) 1.26792(8) 0.65653(8) 0.0186(2) Uani 1 1 d . . . C1 C 0.13740(16) 0.76952(11) 0.76043(10) 0.0135(3) Uani 1 1 d . . . H1 H 0.2517 0.7517 0.7526 0.016 Uiso 1 1 calc R . . C2 C 0.10287(17) 0.72291(12) 0.66484(10) 0.0155(3) Uani 1 1 d . . . H2A H 0.1943 0.7177 0.6023 0.019 Uiso 1 1 calc R . . H2B H 0.0714 0.6489 0.6785 0.019 Uiso 1 1 calc R . . C3 C -0.06443(17) 0.79607(12) 0.55352(10) 0.0160(3) Uani 1 1 d . . . H3A H -0.0815 0.7198 0.5429 0.019 Uiso 1 1 calc R . . H3B H 0.0224 0.8130 0.4942 0.019 Uiso 1 1 calc R . . C4 C -0.21234(17) 0.87816(12) 0.55805(11) 0.0163(3) Uani 1 1 d . . . H4A H -0.2191 0.8918 0.4859 0.020 Uiso 1 1 calc R . . H4B H -0.3040 0.8446 0.5963 0.020 Uiso 1 1 calc R . . C5 C -0.21870(16) 0.98804(11) 0.61088(10) 0.0137(3) Uani 1 1 d . . . C6 C -0.33811(16) 1.07564(12) 0.60782(10) 0.0148(3) Uani 1 1 d . . . H6 H -0.4103 1.0656 0.5707 0.018 Uiso 1 1 calc R . . C7 C -0.35252(16) 1.17645(12) 0.65799(10) 0.0141(3) Uani 1 1 d . . . C8 C -0.24792(17) 1.18951(11) 0.71597(10) 0.0142(3) Uani 1 1 d . . . C9 C -0.12835(16) 1.10504(11) 0.71739(10) 0.0136(3) Uani 1 1 d . . . H9 H -0.0562 1.1154 0.7545 0.016 Uiso 1 1 calc R . . C10 C -0.11178(16) 1.00395(11) 0.66475(10) 0.0132(3) Uani 1 1 d . . . C11 C 0.02299(16) 0.91218(11) 0.66048(10) 0.0130(3) Uani 1 1 d . . . H11 H 0.1099 0.9212 0.5967 0.016 Uiso 1 1 calc R . . C12 C 0.08993(16) 0.89680(11) 0.75589(10) 0.0123(3) Uani 1 1 d . . . H12 H 0.0089 0.9262 0.8216 0.015 Uiso 1 1 calc R . . C13 C 0.32273(16) 0.93393(12) 0.84837(10) 0.0145(3) Uani 1 1 d . . . C14 C 0.24500(17) 0.99639(12) 0.93948(11) 0.0176(3) Uani 1 1 d . . . H14 H 0.1612 1.0545 0.9407 0.021 Uiso 1 1 calc R . . C15 C 0.29319(18) 0.97156(13) 1.02845(11) 0.0210(3) Uani 1 1 d . . . H15 H 0.2423 1.0133 1.0914 0.025 Uiso 1 1 calc R . . C16 C 0.41537(18) 0.88599(13) 1.02605(11) 0.0208(3) Uani 1 1 d . . . H16 H 0.4457 0.8687 1.0879 0.025 Uiso 1 1 calc R . . C17 C 0.49342(18) 0.82572(13) 0.93423(12) 0.0202(3) Uani 1 1 d . . . H17 H 0.5780 0.7683 0.9328 0.024 Uiso 1 1 calc R . . C18 C 0.44705(17) 0.84977(13) 0.84399(11) 0.0182(3) Uani 1 1 d . . . H18 H 0.4997 0.8092 0.7806 0.022 Uiso 1 1 calc R . . C19 C 0.14238(17) 0.58404(11) 0.88401(10) 0.0143(3) Uani 1 1 d . . . C20 C 0.28091(18) 0.57544(13) 0.91166(11) 0.0187(3) Uani 1 1 d . . . H20 H 0.3136 0.6394 0.9320 0.022 Uiso 1 1 calc R . . C21 C 0.37030(18) 0.47132(13) 0.90886(11) 0.0215(3) Uani 1 1 d . . . H21 H 0.4651 0.4639 0.9273 0.026 Uiso 1 1 calc R . . C22 C 0.32181(19) 0.37843(13) 0.87932(11) 0.0218(3) Uani 1 1 d . . . H22 H 0.3839 0.3077 0.8774 0.026 Uiso 1 1 calc R . . C23 C 0.1835(2) 0.38773(13) 0.85248(12) 0.0240(3) Uani 1 1 d . . . H23 H 0.1508 0.3236 0.8327 0.029 Uiso 1 1 calc R . . C24 C 0.09246(18) 0.49141(12) 0.85453(12) 0.0202(3) Uani 1 1 d . . . H24 H -0.0023 0.4986 0.8360 0.024 Uiso 1 1 calc R . . C25 C -0.56563(18) 1.25891(13) 0.59573(12) 0.0195(3) Uani 1 1 d . . . H25A H -0.5059 1.2371 0.5235 0.029 Uiso 1 1 calc R . . H25B H -0.6322 1.3305 0.5965 0.029 Uiso 1 1 calc R . . H25C H -0.6306 1.2029 0.6256 0.029 Uiso 1 1 calc R . . C26 C -0.1624(2) 1.30802(13) 0.81926(12) 0.0230(3) Uani 1 1 d . . . H26A H -0.1546 1.2502 0.8703 0.035 Uiso 1 1 calc R . . H26B H -0.1940 1.3806 0.8552 0.035 Uiso 1 1 calc R . . H26C H -0.0609 1.3058 0.7672 0.035 Uiso 1 1 calc R . . C1S C 0.64844(18) 0.50783(13) 0.66029(12) 0.0206(3) Uani 1 1 d . . . H1S H 0.6282 0.4374 0.6971 0.025 Uiso 1 1 calc R . . Cl1 Cl 0.79730(5) 0.47604(4) 0.54215(4) 0.04017(12) Uani 1 1 d . . . Cl2 Cl 0.71000(5) 0.59294(3) 0.74091(3) 0.02615(9) Uani 1 1 d . . . Cl3 Cl 0.47577(5) 0.57321(3) 0.63430(3) 0.02698(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01349(17) 0.01407(17) 0.01265(15) 0.00194(12) -0.00254(12) -0.00020(13) S2 0.01234(17) 0.01692(17) 0.01554(15) 0.00357(12) -0.00496(13) -0.00320(13) N1 0.0152(6) 0.0125(6) 0.0131(5) -0.0006(4) -0.0053(4) -0.0006(5) O1 0.0244(6) 0.0172(5) 0.0140(4) -0.0010(4) -0.0035(4) -0.0006(4) O2 0.0128(5) 0.0237(6) 0.0211(5) 0.0045(4) -0.0032(4) -0.0015(4) O3 0.0143(5) 0.0315(6) 0.0154(5) 0.0013(4) -0.0023(4) -0.0050(5) O4 0.0199(6) 0.0172(5) 0.0304(6) 0.0080(4) -0.0113(5) -0.0059(4) O5 0.0214(6) 0.0128(5) 0.0230(5) -0.0032(4) -0.0128(4) 0.0009(4) O6 0.0177(5) 0.0159(5) 0.0248(5) -0.0008(4) -0.0125(4) 0.0016(4) C1 0.0127(7) 0.0137(7) 0.0125(6) 0.0012(5) -0.0017(5) -0.0005(5) C2 0.0175(7) 0.0140(7) 0.0133(6) -0.0003(5) -0.0037(5) 0.0007(5) C3 0.0192(7) 0.0164(7) 0.0125(6) -0.0014(5) -0.0051(5) -0.0018(6) C4 0.0181(7) 0.0162(7) 0.0164(6) -0.0009(5) -0.0076(5) -0.0027(6) C5 0.0152(7) 0.0145(7) 0.0115(6) 0.0012(5) -0.0036(5) -0.0026(5) C6 0.0136(7) 0.0184(7) 0.0138(6) 0.0018(5) -0.0059(5) -0.0033(6) C7 0.0126(7) 0.0152(7) 0.0142(6) 0.0024(5) -0.0041(5) -0.0009(5) C8 0.0172(7) 0.0131(6) 0.0130(6) 0.0009(5) -0.0050(5) -0.0028(5) C9 0.0144(7) 0.0150(7) 0.0129(6) 0.0022(5) -0.0061(5) -0.0033(5) C10 0.0134(7) 0.0140(6) 0.0119(6) 0.0029(5) -0.0037(5) -0.0015(5) C11 0.0125(7) 0.0141(7) 0.0124(6) 0.0011(5) -0.0038(5) -0.0020(5) C12 0.0103(6) 0.0131(6) 0.0128(6) 0.0013(5) -0.0028(5) -0.0010(5) C13 0.0121(7) 0.0162(7) 0.0166(6) 0.0015(5) -0.0056(5) -0.0038(5) C14 0.0128(7) 0.0177(7) 0.0216(7) -0.0007(6) -0.0043(5) -0.0013(6) C15 0.0170(8) 0.0274(8) 0.0174(7) -0.0033(6) -0.0022(6) -0.0049(6) C16 0.0181(8) 0.0281(8) 0.0188(7) 0.0041(6) -0.0084(6) -0.0065(6) C17 0.0168(7) 0.0208(7) 0.0246(7) 0.0025(6) -0.0097(6) -0.0004(6) C18 0.0154(7) 0.0199(7) 0.0186(6) -0.0021(5) -0.0043(5) -0.0018(6) C19 0.0147(7) 0.0136(7) 0.0133(6) 0.0029(5) -0.0029(5) -0.0003(5) C20 0.0201(8) 0.0193(7) 0.0181(6) 0.0010(5) -0.0080(6) -0.0026(6) C21 0.0188(8) 0.0248(8) 0.0210(7) 0.0024(6) -0.0085(6) 0.0010(6) C22 0.0243(8) 0.0176(7) 0.0199(7) 0.0033(6) -0.0050(6) 0.0045(6) C23 0.0283(9) 0.0159(7) 0.0294(8) 0.0016(6) -0.0105(7) -0.0045(6) C24 0.0191(8) 0.0173(7) 0.0263(7) 0.0044(6) -0.0093(6) -0.0043(6) C25 0.0170(7) 0.0206(7) 0.0243(7) 0.0047(6) -0.0122(6) -0.0022(6) C26 0.0280(9) 0.0176(7) 0.0296(8) -0.0036(6) -0.0184(7) -0.0022(6) C1S 0.0188(8) 0.0175(7) 0.0241(7) -0.0020(6) -0.0059(6) 0.0011(6) Cl1 0.0245(2) 0.0486(3) 0.0383(2) -0.0231(2) 0.00263(18) 0.0026(2) Cl2 0.0284(2) 0.02067(19) 0.03000(19) -0.00564(15) -0.00986(16) -0.00212(15) Cl3 0.0232(2) 0.0312(2) 0.02339(18) 0.00196(15) -0.00764(15) 0.00679(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4391(11) . ? S1 O1 1.4452(10) . ? S1 C19 1.7681(14) . ? S1 C1 1.8046(13) . ? S2 O3 1.4417(11) . ? S2 O4 1.4455(11) . ? S2 C13 1.7663(13) . ? S2 C12 1.8070(14) . ? N1 C2 1.4539(17) . ? N1 C11 1.4660(18) . ? N1 C3 1.4667(16) . ? O5 C8 1.3752(17) . ? O5 C26 1.4282(17) . ? O6 C7 1.3682(17) . ? O6 C25 1.4330(16) . ? C1 C2 1.5375(18) . ? C1 C12 1.5528(18) . ? C1 H1 1.0000 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.529(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5169(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.3986(18) . ? C5 C6 1.4052(19) . ? C6 C7 1.386(2) . ? C6 H6 0.9500 . ? C7 C8 1.4118(18) . ? C8 C9 1.3771(19) . ? C9 C10 1.4013(19) . ? C9 H9 0.9500 . ? C10 C11 1.5105(19) . ? C11 C12 1.5540(17) . ? C11 H11 1.0000 . ? C12 H12 1.0000 . ? C13 C18 1.389(2) . ? C13 C14 1.392(2) . ? C14 C15 1.388(2) . ? C14 H14 0.9500 . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 C18 1.3944(19) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.389(2) . ? C19 C20 1.394(2) . ? C20 C21 1.391(2) . ? C20 H20 0.9500 . ? C21 C22 1.385(2) . ? C21 H21 0.9500 . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 C24 1.395(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C1S Cl3 1.7626(15) . ? C1S Cl1 1.7628(16) . ? C1S Cl2 1.7685(16) . ? C1S H1S 1.0000 . ? 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 O2 S1 O1 119.00(7) . . ? O2 S1 C19 108.90(7) . . ? O1 S1 C19 108.75(6) . . ? O2 S1 C1 110.20(6) . . ? O1 S1 C1 106.55(6) . . ? C19 S1 C1 102.11(6) . . ? O3 S2 O4 119.29(7) . . ? O3 S2 C13 108.69(7) . . ? O4 S2 C13 108.36(7) . . ? O3 S2 C12 107.39(6) . . ? O4 S2 C12 107.55(6) . . ? C13 S2 C12 104.59(6) . . ? C2 N1 C11 105.11(11) . . ? C2 N1 C3 115.39(11) . . ? C11 N1 C3 110.01(10) . . ? C8 O5 C26 116.02(11) . . ? C7 O6 C25 116.78(11) . . ? C2 C1 C12 104.46(10) . . ? C2 C1 S1 112.94(10) . . ? C12 C1 S1 111.32(9) . . ? C2 C1 H1 109.3 . . ? C12 C1 H1 109.3 . . ? S1 C1 H1 109.3 . . ? N1 C2 C1 102.24(11) . . ? N1 C2 H2A 111.3 . . ? C1 C2 H2A 111.3 . . ? N1 C2 H2B 111.3 . . ? C1 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? N1 C3 C4 108.78(11) . . ? N1 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? N1 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 113.39(11) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C10 C5 C6 119.02(13) . . ? C10 C5 C4 122.02(12) . . ? C6 C5 C4 118.94(12) . . ? C7 C6 C5 121.26(12) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? O6 C7 C6 125.81(12) . . ? O6 C7 C8 115.19(12) . . ? C6 C7 C8 119.01(13) . . ? O5 C8 C9 124.49(12) . . ? O5 C8 C7 115.44(12) . . ? C9 C8 C7 120.08(13) . . ? C8 C9 C10 120.82(12) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C5 C10 C9 119.71(13) . . ? C5 C10 C11 118.40(12) . . ? C9 C10 C11 121.84(12) . . ? N1 C11 C10 109.58(11) . . ? N1 C11 C12 102.33(10) . . ? C10 C11 C12 118.93(11) . . ? N1 C11 H11 108.5 . . ? C10 C11 H11 108.5 . . ? C12 C11 H11 108.5 . . ? C1 C12 C11 104.16(10) . . ? C1 C12 S2 109.48(9) . . ? C11 C12 S2 110.88(9) . . ? C1 C12 H12 110.7 . . ? C11 C12 H12 110.7 . . ? S2 C12 H12 110.7 . . ? C18 C13 C14 122.05(12) . . ? C18 C13 S2 119.19(11) . . ? C14 C13 S2 118.76(11) . . ? C15 C14 C13 118.22(14) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C14 C15 C16 120.49(14) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.61(13) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.69(14) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C13 C18 C17 118.91(14) . . ? C13 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C24 C19 C20 121.45(13) . . ? C24 C19 S1 119.42(11) . . ? C20 C19 S1 119.09(11) . . ? C21 C20 C19 118.64(14) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C22 C21 C20 120.39(14) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.55(14) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C24 119.94(15) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C19 C24 C23 119.03(14) . . ? C19 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? O6 C25 H25A 109.5 . . ? O6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O5 C26 H26A 109.5 . . ? O5 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O5 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? Cl3 C1S Cl1 110.05(8) . . ? Cl3 C1S Cl2 111.15(8) . . ? Cl1 C1S Cl2 109.44(9) . . ? Cl3 C1S H1S 108.7 . . ? Cl1 C1S H1S 108.7 . . ? Cl2 C1S H1S 108.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.467 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.053