# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ikuya Shibata' _publ_contact_author_email SHIBATA@EPC.OSAKA-U.AC.JP _publ_section_title ; Synthesis of oxazolidinones initiated by regio- and diastereocontrolled crotylation of alpha-dicarbonyl compounds ; loop_ _publ_author_name 'Ikuya Shibata' 'Akio Baba' 'Ryota Kojima' 'Atsush Ninomiya' 'Takashi Nozaki' 'Shinji Tsunoi' ; T.Watanabe ; 'Makoto Yasuda' # Attachment 'CIF_5d.cif' data__n489-060307_ _database_code_depnum_ccdc_archive 'CCDC 729634' #TrackingRef 'CIF_5d.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H16 I N O2 ' _chemical_formula_moiety 'C15 H16 I N O2 ' _chemical_formula_weight 369.20 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.6005(9) _cell_length_b 11.9567(9) _cell_length_c 12.2672(8) _cell_angle_alpha 90.0000 _cell_angle_beta 100.851(2) _cell_angle_gamma 90.0000 _cell_volume 1527.03(20) _cell_formula_units_Z 4 _cell_measurement_reflns_used 13743 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 30.2 _cell_measurement_temperature 296.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728.00 _exptl_absorpt_coefficient_mu 2.096 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 16448 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_theta_max 30.49 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4602 _reflns_number_gt 9074 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.0827 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 9155 _refine_ls_number_parameters 212 _refine_ls_goodness_of_fit_ref 1.618 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0010Fo^2^ + 2.0000\s(Fo^2^) + 0.5000]' _refine_ls_shift/su_max 0.0262 _refine_diff_density_max 3.89 _refine_diff_density_min -3.61 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; I I -0.474 1.812 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 I(1) I 0.15427(3) 0.06477(2) 0.40203(3) 0.07247(10) Uani 1.00 1 d . . . O(1) O 0.2094(2) 0.7681(2) 0.4490(2) 0.0526(7) Uani 1.00 1 d . . . O(3) O 0.0947(2) 0.6534(2) 0.3236(2) 0.0589(8) Uani 1.00 1 d . . . N(1) N 0.2227(3) 0.5845(2) 0.4844(2) 0.0508(9) Uani 1.00 1 d . . . C(1) C 0.1263(4) 0.2892(3) 0.5125(3) 0.0529(12) Uani 1.00 1 d . . . C(2) C 0.3737(5) 0.5795(4) 0.6627(4) 0.0740(16) Uani 1.00 1 d . . . C(3) C 0.2559(5) 0.8250(4) 0.6414(3) 0.0756(15) Uani 1.00 1 d . . . C(4) C 0.5466(5) 0.8897(5) 0.3249(4) 0.097(2) Uani 1.00 1 d . . . C(5) C 0.4329(4) 0.7984(3) 0.5276(3) 0.0613(12) Uani 1.00 1 d . . . C(7) C 0.1687(3) 0.6655(3) 0.4103(3) 0.0470(10) Uani 1.00 1 d . . . C(9) C 0.3038(4) 0.6318(3) 0.5751(2) 0.0499(10) Uani 1.00 1 d . . . C(10) C 0.3042(3) 0.7581(3) 0.5524(3) 0.0509(10) Uani 1.00 1 d . . . C(11) C 0.2034(3) 0.4683(3) 0.4638(2) 0.0454(9) Uani 1.00 1 d . . . C(12) C 0.2386(4) 0.3024(4) 0.3594(3) 0.0588(12) Uani 1.00 1 d . . . C(13) C 0.1401(4) 0.4031(3) 0.5308(3) 0.0553(12) Uani 1.00 1 d . . . C(14) C 0.2514(4) 0.4170(3) 0.3779(3) 0.0550(12) Uani 1.00 1 d . . . C(15) C 0.4829(4) 0.7315(4) 0.4419(3) 0.0600(12) Uani 1.00 1 d . . . C(17) C 0.1733(3) 0.2392(3) 0.4266(3) 0.0495(10) Uani 1.00 1 d . . . C(18) C 0.5295(4) 0.7713(4) 0.3551(3) 0.0650(14) Uani 1.00 1 d . . . H(1) H 0.089(4) 0.269(3) 0.553(3) 0.062(15) Uiso 1.00 1 c . . . H(2) H 0.099(4) 0.448(3) 0.581(3) 0.066(12) Uiso 1.00 1 c . . . H(3) H 0.303(3) 0.465(3) 0.346(3) 0.051(11) Uiso 1.00 1 c . . . H(4) H 0.259(4) 0.263(3) 0.292(3) 0.075(13) Uiso 1.00 1 c . . . H(5) H 0.428(4) 0.631(4) 0.723(3) 0.085(15) Uiso 1.00 1 c . . . H(6) H 0.355(3) 0.512(3) 0.659(3) 0.053(12) Uiso 1.00 1 c . . . H(7) H 0.525(5) 0.709(5) 0.291(4) 0.117(19) Uiso 1.00 1 c . . . H(8) H 0.480(4) 0.639(4) 0.446(3) 0.086(14) Uiso 1.00 1 c . . . H(9) H 0.2868 0.8996 0.6410 0.093 Uiso 1.00 1 c R . . H(10) H 0.2857 0.7925 0.7123 0.093 Uiso 1.00 1 c R . . H(11) H 0.1647 0.8255 0.6262 0.093 Uiso 1.00 1 c R . . H(12) H 0.4712 0.9159 0.2773 0.117 Uiso 1.00 1 c R . . H(13) H 0.6177 0.8964 0.2884 0.117 Uiso 1.00 1 c R . . H(14) H 0.5618 0.9330 0.3910 0.117 Uiso 1.00 1 c R . . H(15) H 0.4213 0.8730 0.5012 0.073 Uiso 1.00 1 c R . . H(16) H 0.4954 0.7970 0.5942 0.073 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.0928(2) 0.04771(17) 0.0727(2) 0.00069(16) 0.00493(16) -0.00813(15) O(1) 0.0572(15) 0.0457(15) 0.0547(14) 0.0003(13) 0.0102(13) 0.0058(12) O(3) 0.0622(16) 0.0658(19) 0.0457(14) -0.0055(14) 0.0024(13) 0.0041(13) N(1) 0.0593(19) 0.0495(19) 0.0444(16) 0.0016(15) 0.0118(15) 0.0078(14) C(1) 0.064(2) 0.047(2) 0.052(2) -0.001(2) 0.020(2) 0.0073(19) C(2) 0.098(3) 0.054(3) 0.062(2) 0.006(2) -0.006(2) 0.009(2) C(3) 0.108(3) 0.061(2) 0.063(2) 0.018(2) 0.031(2) 0.000(2) C(4) 0.099(4) 0.103(4) 0.089(3) -0.032(3) 0.021(3) 0.007(3) C(5) 0.059(2) 0.060(2) 0.063(2) -0.006(2) 0.008(2) -0.010(2) C(7) 0.048(2) 0.051(2) 0.046(2) 0.0057(18) 0.0186(19) 0.0119(18) C(9) 0.057(2) 0.050(2) 0.0416(18) 0.0040(19) 0.0066(17) 0.0064(16) C(10) 0.058(2) 0.048(2) 0.0462(19) -0.0022(19) 0.0081(18) -0.0044(16) C(11) 0.048(2) 0.045(2) 0.0398(18) 0.0007(17) 0.0020(17) 0.0003(15) C(12) 0.068(2) 0.063(2) 0.048(2) 0.004(2) 0.019(2) -0.008(2) C(13) 0.066(2) 0.051(2) 0.057(2) 0.002(2) 0.032(2) 0.0009(18) C(14) 0.058(2) 0.058(2) 0.050(2) -0.001(2) 0.012(2) 0.0094(18) C(15) 0.056(2) 0.058(2) 0.067(2) -0.008(2) 0.013(2) -0.007(2) C(17) 0.052(2) 0.044(2) 0.049(2) 0.0076(17) 0.0015(18) 0.0032(16) C(18) 0.057(2) 0.075(3) 0.063(2) -0.012(2) 0.011(2) -0.008(2) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I(1) C(17) 2.111(3) yes . . O(1) C(7) 1.356(4) yes . . O(1) C(10) 1.468(4) yes . . O(3) C(7) 1.206(4) yes . . N(1) C(7) 1.377(4) yes . . N(1) C(9) 1.392(4) yes . . N(1) C(11) 1.421(4) yes . . C(1) C(13) 1.383(6) yes . . C(1) C(17) 1.383(6) yes . . C(2) C(9) 1.339(6) yes . . C(3) C(10) 1.519(6) yes . . C(4) C(18) 1.483(8) yes . . C(5) C(10) 1.530(6) yes . . C(5) C(15) 1.495(6) yes . . C(9) C(10) 1.536(5) yes . . C(11) C(13) 1.394(6) yes . . C(11) C(14) 1.396(5) yes . . C(12) C(14) 1.392(6) yes . . C(12) C(17) 1.395(6) yes . . C(15) C(18) 1.343(6) yes . . C(1) H(1) 0.73(4) no . . C(2) H(5) 1.05(4) no . . C(2) H(6) 0.84(4) no . . C(3) H(9) 0.950 no . . C(3) H(10) 0.950 no . . C(3) H(11) 0.950 no . . C(4) H(12) 0.950 no . . C(4) H(13) 0.950 no . . C(4) H(14) 0.950 no . . C(5) H(15) 0.950 no . . C(5) H(16) 0.950 no . . C(12) H(4) 1.01(4) no . . C(13) H(2) 0.98(4) no . . C(14) H(3) 0.93(4) no . . C(15) H(8) 1.11(5) no . . C(18) H(7) 1.08(5) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(7) O(1) C(10) 110.5(2) yes . . . C(7) N(1) C(9) 111.1(3) yes . . . C(7) N(1) C(11) 122.9(2) yes . . . C(9) N(1) C(11) 125.8(3) yes . . . C(13) C(1) C(17) 120.5(4) yes . . . C(10) C(5) C(15) 114.8(3) yes . . . O(1) C(7) O(3) 121.9(3) yes . . . O(1) C(7) N(1) 109.8(2) yes . . . O(3) C(7) N(1) 128.3(3) yes . . . N(1) C(9) C(2) 128.1(4) yes . . . N(1) C(9) C(10) 106.0(2) yes . . . C(2) C(9) C(10) 125.7(3) yes . . . O(1) C(10) C(3) 108.0(3) yes . . . O(1) C(10) C(5) 107.1(3) yes . . . O(1) C(10) C(9) 102.3(2) yes . . . C(3) C(10) C(5) 114.3(3) yes . . . C(3) C(10) C(9) 112.0(3) yes . . . C(5) C(10) C(9) 112.2(3) yes . . . N(1) C(11) C(13) 120.8(3) yes . . . N(1) C(11) C(14) 120.2(3) yes . . . C(13) C(11) C(14) 119.0(3) yes . . . C(14) C(12) C(17) 118.7(4) yes . . . C(1) C(13) C(11) 120.2(4) yes . . . C(11) C(14) C(12) 121.1(4) yes . . . C(5) C(15) C(18) 126.9(4) yes . . . I(1) C(17) C(1) 119.9(3) yes . . . I(1) C(17) C(12) 119.7(3) yes . . . C(1) C(17) C(12) 120.4(3) yes . . . C(4) C(18) C(15) 128.1(4) yes . . . C(13) C(1) H(1) 106(3) no . . . C(17) C(1) H(1) 133(3) no . . . C(9) C(2) H(5) 116(2) no . . . C(9) C(2) H(6) 109(2) no . . . H(5) C(2) H(6) 134(3) no . . . C(10) C(3) H(9) 109.1 no . . . C(10) C(3) H(10) 110.1 no . . . C(10) C(3) H(11) 109.2 no . . . H(9) C(3) H(10) 109.5 no . . . H(9) C(3) H(11) 109.5 no . . . H(10) C(3) H(11) 109.5 no . . . C(18) C(4) H(12) 109.9 no . . . C(18) C(4) H(13) 110.1 no . . . C(18) C(4) H(14) 108.5 no . . . H(12) C(4) H(13) 109.5 no . . . H(12) C(4) H(14) 109.5 no . . . H(13) C(4) H(14) 109.5 no . . . C(10) C(5) H(15) 107.5 no . . . C(10) C(5) H(16) 109.1 no . . . C(15) C(5) H(15) 107.7 no . . . C(15) C(5) H(16) 108.3 no . . . H(15) C(5) H(16) 109.5 no . . . C(14) C(12) H(4) 124(2) no . . . C(17) C(12) H(4) 116(2) no . . . C(1) C(13) H(2) 127(2) no . . . C(11) C(13) H(2) 113(2) no . . . C(11) C(14) H(3) 112(2) no . . . C(12) C(14) H(3) 126(2) no . . . C(5) C(15) H(8) 119(2) no . . . C(18) C(15) H(8) 114(2) no . . . C(4) C(18) H(7) 118(3) no . . . C(15) C(18) H(7) 111(3) no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(7) O(1) C(10) C(3) -123.5(3) ? . . . . C(7) O(1) C(10) C(5) 113.0(3) ? . . . . C(7) O(1) C(10) C(9) -5.2(4) ? . . . . C(10) O(1) C(7) O(3) -176.7(3) ? . . . . C(10) O(1) C(7) N(1) 4.1(4) ? . . . . C(7) N(1) C(9) C(2) -179.2(5) ? . . . . C(7) N(1) C(9) C(10) -2.4(4) ? . . . . C(9) N(1) C(7) O(1) -0.9(4) ? . . . . C(9) N(1) C(7) O(3) 179.9(3) ? . . . . C(7) N(1) C(11) C(13) -116.1(4) ? . . . . C(7) N(1) C(11) C(14) 65.8(5) ? . . . . C(11) N(1) C(7) O(1) -176.6(3) ? . . . . C(11) N(1) C(7) O(3) 4.3(6) ? . . . . C(9) N(1) C(11) C(13) 68.9(5) ? . . . . C(9) N(1) C(11) C(14) -109.2(4) ? . . . . C(11) N(1) C(9) C(2) -3.7(7) ? . . . . C(11) N(1) C(9) C(10) 173.1(3) ? . . . . C(13) C(1) C(17) I(1) 178.9(3) ? . . . . C(13) C(1) C(17) C(12) 2.0(6) ? . . . . C(17) C(1) C(13) C(11) -1.1(6) ? . . . . C(10) C(5) C(15) C(18) 132.7(4) ? . . . . C(15) C(5) C(10) O(1) -61.7(4) ? . . . . C(15) C(5) C(10) C(3) 178.7(3) ? . . . . C(15) C(5) C(10) C(9) 49.7(4) ? . . . . N(1) C(9) C(10) O(1) 4.5(4) ? . . . . N(1) C(9) C(10) C(3) 119.9(3) ? . . . . N(1) C(9) C(10) C(5) -109.9(3) ? . . . . C(2) C(9) C(10) O(1) -178.6(4) ? . . . . C(2) C(9) C(10) C(3) -63.2(6) ? . . . . C(2) C(9) C(10) C(5) 67.0(5) ? . . . . N(1) C(11) C(13) C(1) -177.5(3) ? . . . . N(1) C(11) C(14) C(12) 177.1(3) ? . . . . C(13) C(11) C(14) C(12) -1.0(5) ? . . . . C(14) C(11) C(13) C(1) 0.6(5) ? . . . . C(14) C(12) C(17) I(1) -179.2(2) ? . . . . C(14) C(12) C(17) C(1) -2.3(5) ? . . . . C(17) C(12) C(14) C(11) 1.9(5) ? . . . . C(5) C(15) C(18) C(4) 2.1(7) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 I(1) C(1) 3.046(4) ? . . I(1) C(12) 3.053(4) ? . . O(1) O(3) 2.241(3) ? . . O(1) N(1) 2.237(4) ? . . O(1) C(3) 2.417(4) ? . . O(1) C(5) 2.412(4) ? . . O(1) C(9) 2.339(4) ? . . O(1) C(11) 3.591(4) ? . . O(1) C(15) 2.950(5) ? . . O(3) O(1) 2.241(3) ? . . O(3) N(1) 2.325(3) ? . . O(3) C(1) 3.431(5) ? . 3_566 O(3) C(9) 3.454(4) ? . . O(3) C(10) 3.469(4) ? . . O(3) C(11) 2.906(4) ? . . O(3) C(12) 3.581(5) ? . 2_555 O(3) C(13) 3.393(5) ? . 3_566 O(3) C(14) 3.282(5) ? . . N(1) O(1) 2.237(4) ? . . N(1) O(3) 2.325(3) ? . . N(1) C(2) 2.457(5) ? . . N(1) C(3) 3.443(5) ? . . N(1) C(5) 3.367(5) ? . . N(1) C(10) 2.340(4) ? . . N(1) C(13) 2.447(5) ? . . N(1) C(14) 2.441(5) ? . . N(1) C(15) 3.392(5) ? . . C(1) I(1) 3.046(4) ? . . C(1) O(3) 3.431(5) ? . 3_566 C(1) C(7) 3.476(6) ? . 3_566 C(1) C(11) 2.406(5) ? . . C(1) C(12) 2.411(6) ? . . C(1) C(14) 2.765(6) ? . . C(2) N(1) 2.457(5) ? . . C(2) C(3) 3.182(7) ? . . C(2) C(5) 3.221(7) ? . . C(2) C(7) 3.583(6) ? . . C(2) C(10) 2.560(6) ? . . C(2) C(11) 3.054(6) ? . . C(2) C(13) 3.420(6) ? . . C(3) O(1) 2.417(4) ? . . C(3) N(1) 3.443(5) ? . . C(3) C(2) 3.182(7) ? . . C(3) C(5) 2.561(7) ? . . C(3) C(7) 3.399(5) ? . . C(3) C(9) 2.533(6) ? . . C(4) C(5) 3.156(7) ? . . C(4) C(12) 3.573(6) ? . 2_555 C(4) C(15) 2.542(7) ? . . C(5) O(1) 2.412(4) ? . . C(5) N(1) 3.367(5) ? . . C(5) C(2) 3.221(7) ? . . C(5) C(3) 2.561(7) ? . . C(5) C(4) 3.156(7) ? . . C(5) C(7) 3.305(5) ? . . C(5) C(9) 2.545(6) ? . . C(5) C(18) 2.539(6) ? . . C(7) C(1) 3.476(6) ? . 3_566 C(7) C(2) 3.583(6) ? . . C(7) C(3) 3.399(5) ? . . C(7) C(5) 3.305(5) ? . . C(7) C(9) 2.284(4) ? . . C(7) C(10) 2.321(5) ? . . C(7) C(11) 2.457(5) ? . . C(7) C(13) 3.506(5) ? . . C(7) C(13) 3.577(6) ? . 3_566 C(7) C(14) 3.144(5) ? . . C(7) C(15) 3.374(5) ? . . C(9) O(1) 2.339(4) ? . . C(9) O(3) 3.454(4) ? . . C(9) C(3) 2.533(6) ? . . C(9) C(5) 2.545(6) ? . . C(9) C(7) 2.284(4) ? . . C(9) C(11) 2.505(5) ? . . C(9) C(13) 3.230(5) ? . . C(9) C(14) 3.500(5) ? . . C(9) C(15) 2.977(6) ? . . C(10) O(3) 3.469(4) ? . . C(10) N(1) 2.340(4) ? . . C(10) C(2) 2.560(6) ? . . C(10) C(7) 2.321(5) ? . . C(10) C(15) 2.548(6) ? . . C(11) O(1) 3.591(4) ? . . C(11) O(3) 2.906(4) ? . . C(11) C(1) 2.406(5) ? . . C(11) C(2) 3.054(6) ? . . C(11) C(7) 2.457(5) ? . . C(11) C(9) 2.505(5) ? . . C(11) C(12) 2.428(5) ? . . C(11) C(17) 2.785(5) ? . . C(12) I(1) 3.053(4) ? . . C(12) O(3) 3.581(5) ? . 2_545 C(12) C(1) 2.411(6) ? . . C(12) C(4) 3.573(6) ? . 2_545 C(12) C(11) 2.428(5) ? . . C(12) C(13) 2.791(6) ? . . C(12) C(15) 3.480(5) ? . 3_666 C(12) C(18) 3.510(5) ? . 2_545 C(13) O(3) 3.393(5) ? . 3_566 C(13) N(1) 2.447(5) ? . . C(13) C(2) 3.420(6) ? . . C(13) C(7) 3.506(5) ? . . C(13) C(7) 3.577(6) ? . 3_566 C(13) C(9) 3.230(5) ? . . C(13) C(12) 2.791(6) ? . . C(13) C(14) 2.403(6) ? . . C(13) C(17) 2.401(5) ? . . C(14) O(3) 3.282(5) ? . . C(14) N(1) 2.441(5) ? . . C(14) C(1) 2.765(6) ? . . C(14) C(7) 3.144(5) ? . . C(14) C(9) 3.500(5) ? . . C(14) C(13) 2.403(6) ? . . C(14) C(17) 2.399(6) ? . . C(15) O(1) 2.950(5) ? . . C(15) N(1) 3.392(5) ? . . C(15) C(4) 2.542(7) ? . . C(15) C(7) 3.374(5) ? . . C(15) C(9) 2.977(6) ? . . C(15) C(10) 2.548(6) ? . . C(15) C(12) 3.480(5) ? . 3_666 C(17) C(11) 2.785(5) ? . . C(17) C(13) 2.401(5) ? . . C(17) C(14) 2.399(6) ? . . C(18) C(5) 2.539(6) ? . . C(18) C(12) 3.510(5) ? . 2_555 I(1) H(1) 3.21(4) ? . . I(1) H(3) 3.37(3) ? . 2_545 I(1) H(4) 3.04(4) ? . . I(1) H(7) 3.24(5) ? . 2_545 I(1) H(9) 3.594 ? . 1_545 I(1) H(11) 3.582 ? . 3_566 I(1) H(14) 3.554 ? . 3_666 O(1) H(1) 3.19(4) ? . 3_566 O(1) H(4) 3.03(4) ? . 2_555 O(1) H(8) 3.26(4) ? . . O(1) H(9) 2.823 ? . . O(1) H(10) 3.192 ? . . O(1) H(11) 2.410 ? . . O(1) H(15) 2.548 ? . . O(1) H(16) 3.233 ? . . O(3) H(1) 2.84(4) ? . 3_566 O(3) H(2) 2.82(4) ? . 3_566 O(3) H(3) 3.13(3) ? . . O(3) H(4) 2.64(4) ? . 2_555 O(3) H(5) 3.23(4) ? . 4_464 O(3) H(10) 3.365 ? . 4_464 O(3) H(12) 3.124 ? . 2_545 O(3) H(16) 2.874 ? . 4_464 N(1) H(2) 2.52(4) ? . . N(1) H(2) 3.38(4) ? . 3_566 N(1) H(3) 2.49(4) ? . . N(1) H(5) 3.35(4) ? . . N(1) H(6) 2.49(3) ? . . N(1) H(8) 2.92(4) ? . . N(1) H(11) 3.480 ? . . C(1) H(2) 2.12(4) ? . . C(1) H(4) 3.29(4) ? . . C(1) H(10) 3.329 ? . 2_546 C(1) H(11) 3.509 ? . 3_566 C(2) H(2) 3.29(4) ? . . C(2) H(3) 3.49(4) ? . 3_666 C(2) H(8) 3.15(4) ? . . C(2) H(8) 3.43(5) ? . 3_666 C(2) H(10) 2.818 ? . . C(2) H(13) 3.376 ? . 4_465 C(2) H(16) 3.089 ? . . C(3) H(5) 3.00(4) ? . . C(3) H(7) 3.35(6) ? . 4_465 C(3) H(14) 3.542 ? . 3_676 C(3) H(15) 2.738 ? . . C(3) H(16) 2.729 ? . . C(4) H(7) 2.21(6) ? . . C(4) H(8) 3.48(5) ? . . C(4) H(9) 3.060 ? . 3_676 C(4) H(15) 2.750 ? . . C(4) H(15) 3.527 ? . 3_676 C(5) H(5) 3.13(5) ? . . C(5) H(7) 3.40(6) ? . . C(5) H(8) 2.25(5) ? . . C(5) H(9) 2.571 ? . . C(5) H(10) 2.984 ? . . C(5) H(11) 3.309 ? . . C(5) H(12) 3.470 ? . . C(5) H(14) 2.852 ? . . C(5) H(14) 3.361 ? . 3_676 C(7) H(1) 2.96(4) ? . 3_566 C(7) H(2) 3.50(4) ? . . C(7) H(2) 3.17(4) ? . 3_566 C(7) H(3) 2.97(4) ? . . C(7) H(4) 2.97(4) ? . 2_555 C(7) H(8) 3.26(4) ? . . C(7) H(11) 3.274 ? . . C(9) H(2) 3.10(4) ? . . C(9) H(3) 3.45(3) ? . . C(9) H(5) 2.03(4) ? . . C(9) H(6) 1.79(4) ? . . C(9) H(8) 2.66(4) ? . . C(9) H(9) 3.316 ? . . C(9) H(10) 2.585 ? . . C(9) H(11) 2.878 ? . . C(9) H(13) 3.577 ? . 4_465 C(9) H(15) 3.335 ? . . C(9) H(16) 2.811 ? . . C(10) H(5) 2.72(4) ? . . C(10) H(6) 3.23(4) ? . . C(10) H(8) 2.85(5) ? . . C(10) H(9) 2.038 ? . . C(10) H(10) 2.049 ? . . C(10) H(11) 2.040 ? . . C(10) H(15) 2.029 ? . . C(10) H(16) 2.048 ? . . C(11) H(1) 2.98(4) ? . . C(11) H(2) 1.98(4) ? . . C(11) H(2) 3.31(4) ? . 3_566 C(11) H(3) 1.95(4) ? . . C(11) H(4) 3.36(4) ? . . C(11) H(6) 2.68(3) ? . . C(11) H(8) 3.57(4) ? . 3_666 C(11) H(12) 3.241 ? . 2_545 C(12) H(1) 3.12(4) ? . . C(12) H(3) 2.08(4) ? . . C(12) H(7) 3.24(5) ? . 2_545 C(12) H(8) 3.53(4) ? . 3_666 C(12) H(12) 2.862 ? . 2_545 C(12) H(16) 3.014 ? . 3_666 C(13) H(1) 1.73(4) ? . . C(13) H(2) 3.19(4) ? . 3_566 C(13) H(3) 3.19(4) ? . . C(13) H(6) 2.83(3) ? . . C(13) H(10) 3.371 ? . 2_546 C(14) H(1) 3.48(4) ? . . C(14) H(2) 3.23(4) ? . . C(14) H(4) 2.13(4) ? . . C(14) H(8) 3.58(4) ? . . C(14) H(8) 3.30(4) ? . 3_666 C(14) H(12) 2.738 ? . 2_545 C(15) H(4) 3.49(3) ? . 2_555 C(15) H(7) 2.00(5) ? . . C(15) H(12) 2.977 ? . . C(15) H(13) 3.239 ? . . C(15) H(14) 2.664 ? . . C(15) H(15) 2.000 ? . . C(15) H(16) 2.007 ? . . C(17) H(1) 1.96(4) ? . . C(17) H(2) 3.31(4) ? . . C(17) H(3) 3.27(4) ? . . C(17) H(4) 2.05(4) ? . . C(17) H(7) 3.09(5) ? . 2_545 C(17) H(12) 3.409 ? . 2_545 C(17) H(16) 3.596 ? . 3_666 C(18) H(4) 3.24(4) ? . 2_555 C(18) H(8) 2.07(4) ? . . C(18) H(10) 3.580 ? . 4_564 C(18) H(11) 3.577 ? . 4_564 C(18) H(12) 2.015 ? . . C(18) H(13) 2.017 ? . . C(18) H(14) 1.999 ? . . C(18) H(15) 2.604 ? . . C(18) H(16) 3.038 ? . . H(1) I(1) 3.21(4) ? . . H(1) O(1) 3.19(4) ? . 3_566 H(1) O(3) 2.84(4) ? . 3_566 H(1) C(7) 2.96(4) ? . 3_566 H(1) C(11) 2.98(4) ? . . H(1) C(12) 3.12(4) ? . . H(1) C(13) 1.73(4) ? . . H(1) C(14) 3.48(4) ? . . H(1) C(17) 1.96(4) ? . . H(1) H(2) 2.17(6) ? . . H(1) H(5) 3.24(6) ? . 2_546 H(1) H(10) 2.952 ? . 2_546 H(1) H(11) 3.330 ? . 3_566 H(2) O(3) 2.82(4) ? . 3_566 H(2) N(1) 2.52(4) ? . . H(2) N(1) 3.38(4) ? . 3_566 H(2) C(1) 2.12(4) ? . . H(2) C(2) 3.29(4) ? . . H(2) C(7) 3.50(4) ? . . H(2) C(7) 3.17(4) ? . 3_566 H(2) C(9) 3.10(4) ? . . H(2) C(11) 1.98(4) ? . . H(2) C(11) 3.31(4) ? . 3_566 H(2) C(13) 3.19(4) ? . 3_566 H(2) C(14) 3.23(4) ? . . H(2) C(17) 3.31(4) ? . . H(2) H(1) 2.17(6) ? . . H(2) H(2) 2.89(5) ? . 3_566 H(2) H(6) 2.81(5) ? . . H(2) H(9) 3.447 ? . 2_546 H(2) H(10) 3.196 ? . 2_546 H(2) H(12) 3.396 ? . 4_465 H(2) H(13) 3.130 ? . 4_465 H(3) I(1) 3.37(3) ? . 2_555 H(3) O(3) 3.13(3) ? . . H(3) N(1) 2.49(4) ? . . H(3) C(2) 3.49(4) ? . 3_666 H(3) C(7) 2.97(4) ? . . H(3) C(9) 3.45(3) ? . . H(3) C(11) 1.95(4) ? . . H(3) C(12) 2.08(4) ? . . H(3) C(13) 3.19(4) ? . . H(3) C(17) 3.27(4) ? . . H(3) H(4) 2.53(6) ? . . H(3) H(5) 3.33(6) ? . 3_666 H(3) H(8) 2.91(6) ? . . H(3) H(8) 3.34(5) ? . 3_666 H(3) H(12) 3.067 ? . 2_545 H(4) I(1) 3.04(4) ? . . H(4) O(1) 3.03(4) ? . 2_545 H(4) O(3) 2.64(4) ? . 2_545 H(4) C(1) 3.29(4) ? . . H(4) C(7) 2.97(4) ? . 2_545 H(4) C(11) 3.36(4) ? . . H(4) C(14) 2.13(4) ? . . H(4) C(15) 3.49(3) ? . 2_545 H(4) C(17) 2.05(4) ? . . H(4) C(18) 3.24(4) ? . 2_545 H(4) H(3) 2.53(6) ? . . H(4) H(5) 3.59(6) ? . 3_666 H(4) H(7) 3.06(6) ? . 2_545 H(4) H(12) 3.037 ? . 2_545 H(4) H(16) 2.810 ? . 3_666 H(5) O(3) 3.23(4) ? . 4_565 H(5) N(1) 3.35(4) ? . . H(5) C(3) 3.00(4) ? . . H(5) C(5) 3.13(5) ? . . H(5) C(9) 2.03(4) ? . . H(5) C(10) 2.72(4) ? . . H(5) H(1) 3.24(6) ? . 2_556 H(5) H(3) 3.33(6) ? . 3_666 H(5) H(4) 3.59(6) ? . 3_666 H(5) H(6) 1.74(6) ? . . H(5) H(8) 3.54(6) ? . . H(5) H(10) 2.439 ? . . H(5) H(13) 3.546 ? . 4_465 H(5) H(16) 2.714 ? . . H(6) N(1) 2.49(3) ? . . H(6) C(9) 1.79(4) ? . . H(6) C(10) 3.23(4) ? . . H(6) C(11) 2.68(3) ? . . H(6) C(13) 2.83(3) ? . . H(6) H(2) 2.81(5) ? . . H(6) H(5) 1.74(6) ? . . H(6) H(7) 2.94(7) ? . 3_666 H(6) H(8) 3.49(6) ? . . H(6) H(8) 2.97(6) ? . 3_666 H(6) H(9) 3.384 ? . 2_546 H(6) H(10) 3.526 ? . . H(6) H(10) 3.529 ? . 2_546 H(6) H(11) 3.482 ? . 2_546 H(6) H(13) 3.400 ? . 4_465 H(7) I(1) 3.24(5) ? . 2_555 H(7) C(3) 3.35(6) ? . 4_564 H(7) C(4) 2.21(6) ? . . H(7) C(5) 3.40(6) ? . . H(7) C(12) 3.24(5) ? . 2_555 H(7) C(15) 2.00(5) ? . . H(7) C(17) 3.09(5) ? . 2_555 H(7) H(4) 3.06(6) ? . 2_555 H(7) H(6) 2.94(7) ? . 3_666 H(7) H(8) 2.22(7) ? . . H(7) H(10) 3.095 ? . 4_564 H(7) H(11) 2.754 ? . 4_564 H(7) H(12) 2.538 ? . . H(7) H(13) 2.451 ? . . H(7) H(14) 2.943 ? . . H(7) H(15) 3.574 ? . . H(8) O(1) 3.26(4) ? . . H(8) N(1) 2.92(4) ? . . H(8) C(2) 3.15(4) ? . . H(8) C(2) 3.43(5) ? . 3_666 H(8) C(4) 3.48(5) ? . . H(8) C(5) 2.25(5) ? . . H(8) C(7) 3.26(4) ? . . H(8) C(9) 2.66(4) ? . . H(8) C(10) 2.85(5) ? . . H(8) C(11) 3.57(4) ? . 3_666 H(8) C(12) 3.53(4) ? . 3_666 H(8) C(14) 3.58(4) ? . . H(8) C(14) 3.30(4) ? . 3_666 H(8) C(18) 2.07(4) ? . . H(8) H(3) 2.91(6) ? . . H(8) H(3) 3.34(5) ? . 3_666 H(8) H(5) 3.54(6) ? . . H(8) H(6) 3.49(6) ? . . H(8) H(6) 2.97(6) ? . 3_666 H(8) H(7) 2.22(7) ? . . H(8) H(8) 3.56(7) ? . 3_666 H(8) H(15) 2.976 ? . . H(8) H(16) 2.607 ? . . H(9) I(1) 3.594 ? . 1_565 H(9) O(1) 2.823 ? . . H(9) C(4) 3.060 ? . 3_676 H(9) C(5) 2.571 ? . . H(9) C(9) 3.316 ? . . H(9) C(10) 2.038 ? . . H(9) H(2) 3.447 ? . 2_556 H(9) H(6) 3.384 ? . 2_556 H(9) H(10) 1.551 ? . . H(9) H(11) 1.551 ? . . H(9) H(12) 3.389 ? . 3_676 H(9) H(13) 2.719 ? . 3_676 H(9) H(14) 2.640 ? . 3_676 H(9) H(15) 2.448 ? . . H(9) H(16) 2.683 ? . . H(10) O(1) 3.192 ? . . H(10) O(3) 3.365 ? . 4_565 H(10) C(1) 3.329 ? . 2_556 H(10) C(2) 2.818 ? . . H(10) C(5) 2.984 ? . . H(10) C(9) 2.585 ? . . H(10) C(10) 2.049 ? . . H(10) C(13) 3.371 ? . 2_556 H(10) C(18) 3.580 ? . 4_465 H(10) H(1) 2.952 ? . 2_556 H(10) H(2) 3.196 ? . 2_556 H(10) H(5) 2.439 ? . . H(10) H(6) 3.526 ? . . H(10) H(6) 3.529 ? . 2_556 H(10) H(7) 3.095 ? . 4_465 H(10) H(9) 1.551 ? . . H(10) H(11) 1.551 ? . . H(10) H(13) 3.126 ? . 4_465 H(10) H(15) 3.332 ? . . H(10) H(16) 2.873 ? . . H(11) I(1) 3.582 ? . 3_566 H(11) O(1) 2.410 ? . . H(11) N(1) 3.480 ? . . H(11) C(1) 3.509 ? . 3_566 H(11) C(5) 3.309 ? . . H(11) C(7) 3.274 ? . . H(11) C(9) 2.878 ? . . H(11) C(10) 2.040 ? . . H(11) C(18) 3.577 ? . 4_465 H(11) H(1) 3.330 ? . 3_566 H(11) H(6) 3.482 ? . 2_556 H(11) H(7) 2.754 ? . 4_465 H(11) H(9) 1.551 ? . . H(11) H(10) 1.551 ? . . H(11) H(13) 3.409 ? . 4_465 H(11) H(15) 3.412 ? . . H(12) O(3) 3.124 ? . 2_555 H(12) C(5) 3.470 ? . . H(12) C(11) 3.241 ? . 2_555 H(12) C(12) 2.862 ? . 2_555 H(12) C(14) 2.738 ? . 2_555 H(12) C(15) 2.977 ? . . H(12) C(17) 3.409 ? . 2_555 H(12) C(18) 2.015 ? . . H(12) H(2) 3.396 ? . 4_564 H(12) H(3) 3.067 ? . 2_555 H(12) H(4) 3.037 ? . 2_555 H(12) H(7) 2.538 ? . . H(12) H(9) 3.389 ? . 3_676 H(12) H(13) 1.551 ? . . H(12) H(14) 1.551 ? . . H(12) H(15) 2.939 ? . . H(13) C(2) 3.376 ? . 4_564 H(13) C(9) 3.577 ? . 4_564 H(13) C(15) 3.239 ? . . H(13) C(18) 2.017 ? . . H(13) H(2) 3.130 ? . 4_564 H(13) H(5) 3.546 ? . 4_564 H(13) H(6) 3.400 ? . 4_564 H(13) H(7) 2.451 ? . . H(13) H(9) 2.719 ? . 3_676 H(13) H(10) 3.126 ? . 4_564 H(13) H(11) 3.409 ? . 4_564 H(13) H(12) 1.551 ? . . H(13) H(14) 1.551 ? . . H(14) I(1) 3.554 ? . 3_666 H(14) C(3) 3.542 ? . 3_676 H(14) C(5) 2.852 ? . . H(14) C(5) 3.361 ? . 3_676 H(14) C(15) 2.664 ? . . H(14) C(18) 1.999 ? . . H(14) H(7) 2.943 ? . . H(14) H(9) 2.640 ? . 3_676 H(14) H(12) 1.551 ? . . H(14) H(13) 1.551 ? . . H(14) H(14) 3.572 ? . 3_676 H(14) H(15) 2.307 ? . . H(14) H(15) 2.659 ? . 3_676 H(14) H(16) 3.165 ? . . H(14) H(16) 3.295 ? . 3_676 H(15) O(1) 2.548 ? . . H(15) C(3) 2.738 ? . . H(15) C(4) 2.750 ? . . H(15) C(4) 3.527 ? . 3_676 H(15) C(9) 3.335 ? . . H(15) C(10) 2.029 ? . . H(15) C(15) 2.000 ? . . H(15) C(18) 2.604 ? . . H(15) H(7) 3.574 ? . . H(15) H(8) 2.976 ? . . H(15) H(9) 2.448 ? . . H(15) H(10) 3.332 ? . . H(15) H(11) 3.412 ? . . H(15) H(12) 2.939 ? . . H(15) H(14) 2.307 ? . . H(15) H(14) 2.659 ? . 3_676 H(15) H(15) 3.467 ? . 3_676 H(15) H(16) 1.551 ? . . H(16) O(1) 3.233 ? . . H(16) O(3) 2.874 ? . 4_565 H(16) C(2) 3.089 ? . . H(16) C(3) 2.729 ? . . H(16) C(9) 2.811 ? . . H(16) C(10) 2.048 ? . . H(16) C(12) 3.014 ? . 3_666 H(16) C(15) 2.007 ? . . H(16) C(17) 3.596 ? . 3_666 H(16) C(18) 3.038 ? . . H(16) H(4) 2.810 ? . 3_666 H(16) H(5) 2.714 ? . . H(16) H(8) 2.607 ? . . H(16) H(9) 2.683 ? . . H(16) H(10) 2.873 ? . . H(16) H(14) 3.165 ? . . H(16) H(14) 3.295 ? . 3_676 H(16) H(15) 1.551 ? . . #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ # Attachment 'CIF_7.cif' #------------------------------------------------------------------------------ data_20050226ninomiya140 _database_code_depnum_ccdc_archive 'CCDC 729635' #TrackingRef 'CIF_7.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C20 H19 N O5 S ' _chemical_formula_moiety 'C20 H19 N O5 S ' _chemical_formula_weight 385.43 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 7.868(1) _cell_length_b 16.732(3) _cell_length_c 7.761(1) _cell_angle_alpha 94.34(1) _cell_angle_beta 107.74(1) _cell_angle_gamma 92.45(1) _cell_volume 968.0(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.5 _cell_measurement_theta_max 14.1 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 6013 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_theta_max 30.00 _diffrn_measured_fraction_theta_max 1.0016 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.0016 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.46 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5631 _reflns_number_gt 2089 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1873 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 5631 _refine_ls_number_parameters 308 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0612 _refine_diff_density_max 0.55 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S S 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S 0.3318(1) 0.31372(6) 0.4103(1) 0.0621(3) Uani 1.00 d . . . O(1) O 0.7251(3) 0.3825(2) 0.5405(3) 0.0742(9) Uani 1.00 d . . . O(2) O 0.4246(3) 0.1510(2) 0.2285(3) 0.0717(8) Uani 1.00 d . . . O(3) O 0.8193(3) 0.2679(1) 0.4504(3) 0.0531(7) Uani 1.00 d . . . O(4) O 0.2084(3) 0.2461(2) 0.3817(4) 0.093(1) Uani 1.00 d . . . O(5) O 0.3788(4) 0.3656(2) 0.5731(3) 0.092(1) Uani 1.00 d . . . N(1) N 0.5249(3) 0.2713(2) 0.4056(3) 0.0500(8) Uani 1.00 d . . . C(1) C 0.6971(4) 0.3149(2) 0.4750(4) 0.0491(10) Uani 1.00 d . . . C(2) C 0.5411(4) 0.1972(2) 0.3190(4) 0.052(1) Uani 1.00 d . . . C(3) C 0.7408(4) 0.1887(2) 0.3625(4) 0.0461(9) Uani 1.00 d . . . C(4) C 0.7918(5) 0.1746(2) 0.1886(5) 0.055(1) Uani 1.00 d . . . C(5) C 0.7400(6) 0.2390(2) 0.0652(5) 0.067(1) Uani 1.00 d . . . C(6) C 0.6136(6) 0.2346(3) -0.0930(5) 0.080(1) Uani 1.00 d . . . C(7) C 0.4971(6) 0.1641(4) -0.1856(6) 0.109(2) Uani 1.00 d . . . C(8) C 0.8036(4) 0.1262(2) 0.4972(4) 0.0477(9) Uani 1.00 d . . . C(9) C 0.9365(5) 0.1466(2) 0.6594(5) 0.066(1) Uani 1.00 d . . . C(10) C 0.9894(7) 0.0882(3) 0.7801(6) 0.088(2) Uani 1.00 d . . . C(11) C 0.9146(6) 0.0131(3) 0.7429(6) 0.079(2) Uani 1.00 d . . . C(12) C 0.7846(7) -0.0070(3) 0.5808(7) 0.084(2) Uani 1.00 d . . . C(13) C 0.7289(6) 0.0482(2) 0.4580(5) 0.069(1) Uani 1.00 d . . . C(14) C 0.2809(4) 0.3688(2) 0.2217(4) 0.0492(9) Uani 1.00 d . . . C(15) C 0.1935(5) 0.3315(2) 0.0512(5) 0.070(1) Uani 1.00 d . . . C(16) C 0.1554(6) 0.3752(2) -0.0965(5) 0.072(1) Uani 1.00 d . . . C(17) C 0.1994(5) 0.4563(2) -0.0785(4) 0.058(1) Uani 1.00 d . . . C(18) C 0.2860(6) 0.4918(2) 0.0935(6) 0.077(1) Uani 1.00 d . . . C(19) C 0.3270(6) 0.4493(2) 0.2427(5) 0.072(1) Uani 1.00 d . . . C(20) C 0.1527(8) 0.5030(3) -0.2422(7) 0.090(2) Uani 1.00 d . . . H(1) H 0.914(5) 0.171(2) 0.226(4) 0.062(9) Uiso 1.00 calc . . . H(2) H 0.738(4) 0.121(2) 0.132(4) 0.060(9) Uiso 1.00 calc . . . H(3) H 0.801(5) 0.283(2) 0.107(5) 0.08(1) Uiso 1.00 calc . . . H(4) H 0.591(6) 0.295(3) -0.151(6) 0.13(1) Uiso 1.00 calc . . . H(5) H 0.3649 0.1716 -0.1992 0.1287 Uiso 1.00 calc . . . H(6) H 0.5279 0.1131 -0.1155 0.1287 Uiso 1.00 calc . . . H(7) H 0.5052 0.1489 -0.3129 0.1287 Uiso 1.00 calc . . . H(8) H 0.989(5) 0.201(2) 0.696(5) 0.08(1) Uiso 1.00 calc . . . H(9) H 1.064(6) 0.099(3) 0.878(6) 0.09(1) Uiso 1.00 calc . . . H(10) H 0.954(5) -0.028(2) 0.823(5) 0.08(1) Uiso 1.00 calc . . . H(11) H 0.742(5) -0.053(2) 0.553(5) 0.08(1) Uiso 1.00 calc . . . H(12) H 0.646(6) 0.035(3) 0.351(6) 0.11(1) Uiso 1.00 calc . . . H(13) H 0.169(5) 0.276(2) 0.040(5) 0.09(1) Uiso 1.00 calc . . . H(14) H 0.088(5) 0.356(2) -0.208(5) 0.09(1) Uiso 1.00 calc . . . H(15) H 0.316(5) 0.545(3) 0.113(5) 0.10(1) Uiso 1.00 calc . . . H(16) H 0.383(5) 0.474(2) 0.348(6) 0.10(1) Uiso 1.00 calc . . . H(17) H 0.071(8) 0.474(4) -0.344(8) 0.179(9) Uiso 1.00 calc . . . H(18) H 0.105(7) 0.548(3) -0.222(7) 0.13(1) Uiso 1.00 calc . . . H(19) H 0.251(8) 0.519(4) -0.256(8) 0.163(8) Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0538(5) 0.0873(7) 0.0540(5) 0.0251(5) 0.0232(4) 0.0227(5) O(1) 0.087(2) 0.051(2) 0.079(2) 0.008(1) 0.018(1) -0.006(1) O(2) 0.060(2) 0.073(2) 0.067(2) -0.022(1) 0.004(1) 0.001(1) O(3) 0.046(1) 0.044(1) 0.062(1) 0.001(1) 0.008(1) 0.003(1) O(4) 0.055(2) 0.123(2) 0.115(2) 0.012(2) 0.036(1) 0.060(2) O(5) 0.117(2) 0.121(2) 0.047(1) 0.058(2) 0.031(1) 0.010(1) N(1) 0.049(2) 0.055(2) 0.048(1) 0.014(1) 0.014(1) 0.012(1) C(1) 0.057(2) 0.047(2) 0.042(2) 0.009(2) 0.011(1) 0.009(2) C(2) 0.056(2) 0.054(2) 0.046(2) 0.005(2) 0.014(2) 0.015(2) C(3) 0.048(2) 0.038(2) 0.050(2) 0.004(1) 0.012(1) 0.002(1) C(4) 0.049(2) 0.056(2) 0.060(2) 0.004(2) 0.016(2) 0.004(2) C(5) 0.088(3) 0.057(2) 0.060(2) -0.003(2) 0.028(2) 0.007(2) C(6) 0.096(3) 0.090(3) 0.057(2) 0.010(3) 0.026(2) 0.019(2) C(7) 0.097(3) 0.160(5) 0.057(3) -0.018(3) 0.006(2) 0.010(3) C(8) 0.050(2) 0.043(2) 0.050(2) 0.010(1) 0.015(1) 0.004(1) C(9) 0.069(2) 0.051(2) 0.066(2) 0.007(2) 0.001(2) 0.009(2) C(10) 0.097(4) 0.085(3) 0.066(3) 0.022(3) -0.003(2) 0.015(3) C(11) 0.108(3) 0.065(3) 0.072(3) 0.031(3) 0.029(3) 0.027(2) C(12) 0.115(4) 0.049(3) 0.094(3) 0.008(3) 0.039(3) 0.017(3) C(13) 0.087(3) 0.045(2) 0.067(3) 0.003(2) 0.013(2) 0.008(2) C(14) 0.047(2) 0.056(2) 0.044(2) 0.017(2) 0.011(1) 0.007(1) C(15) 0.082(3) 0.056(3) 0.061(2) -0.003(2) 0.007(2) 0.007(2) C(16) 0.086(3) 0.068(3) 0.046(2) 0.000(2) -0.003(2) 0.006(2) C(17) 0.062(2) 0.059(2) 0.053(2) 0.017(2) 0.016(2) 0.013(2) C(18) 0.104(3) 0.043(2) 0.071(3) 0.013(2) 0.010(2) 0.005(2) C(19) 0.089(3) 0.058(3) 0.053(2) 0.015(2) 0.000(2) -0.004(2) C(20) 0.111(4) 0.092(4) 0.070(3) 0.029(3) 0.023(3) 0.037(3) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) O(4) 1.418(3) . . yes S(1) O(5) 1.417(3) . . yes S(1) N(1) 1.713(3) . . yes S(1) C(14) 1.742(3) . . yes O(1) C(1) 1.188(4) . . yes O(2) C(2) 1.182(4) . . yes O(3) C(1) 1.316(4) . . yes O(3) C(3) 1.462(3) . . yes N(1) C(1) 1.439(4) . . yes N(1) C(2) 1.394(4) . . yes C(2) C(3) 1.518(4) . . yes C(3) C(4) 1.526(4) . . yes C(3) C(8) 1.525(4) . . yes C(4) C(5) 1.484(5) . . yes C(4) H(1) 0.92(3) . . no C(4) H(2) 0.98(3) . . no C(5) C(6) 1.319(5) . . yes C(5) H(3) 0.84(4) . . no C(6) C(7) 1.458(6) . . yes C(6) H(4) 1.14(5) . . no C(7) H(5) 1.027 . . no C(7) H(6) 1.044 . . no C(7) H(7) 1.023 . . no C(8) C(9) 1.377(4) . . yes C(8) C(13) 1.382(5) . . yes C(9) C(10) 1.394(5) . . yes C(9) H(8) 0.97(3) . . no C(10) C(11) 1.337(6) . . yes C(10) H(9) 0.81(4) . . no C(11) C(12) 1.365(6) . . yes C(11) H(10) 0.95(4) . . no C(12) C(13) 1.366(6) . . yes C(12) H(11) 0.82(4) . . no C(13) H(12) 0.89(4) . . no C(14) C(15) 1.377(5) . . yes C(14) C(19) 1.364(5) . . yes C(15) C(16) 1.369(5) . . yes C(15) H(13) 0.94(4) . . no C(16) C(17) 1.371(5) . . yes C(16) H(14) 0.89(4) . . no C(17) C(18) 1.375(5) . . yes C(17) C(20) 1.500(5) . . yes C(18) C(19) 1.367(5) . . yes C(18) H(15) 0.90(4) . . no C(19) H(16) 0.86(4) . . no C(20) H(17) 0.94(6) . . no C(20) H(18) 0.89(5) . . no C(20) H(19) 0.85(6) . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(4) S(1) O(5) 121.4(2) . . . yes O(4) S(1) N(1) 102.9(2) . . . yes O(4) S(1) C(14) 110.9(2) . . . yes O(5) S(1) N(1) 105.7(1) . . . yes O(5) S(1) C(14) 110.7(2) . . . yes N(1) S(1) C(14) 103.3(1) . . . yes C(1) O(3) C(3) 111.8(2) . . . yes S(1) N(1) C(1) 122.1(2) . . . yes S(1) N(1) C(2) 127.6(2) . . . yes C(1) N(1) C(2) 109.8(3) . . . yes O(1) C(1) O(3) 125.3(3) . . . yes O(1) C(1) N(1) 126.0(3) . . . yes O(3) C(1) N(1) 108.6(3) . . . yes O(2) C(2) N(1) 127.5(3) . . . yes O(2) C(2) C(3) 126.9(3) . . . yes N(1) C(2) C(3) 105.5(3) . . . yes O(3) C(3) C(2) 103.3(2) . . . yes O(3) C(3) C(4) 107.9(3) . . . yes O(3) C(3) C(8) 108.7(2) . . . yes C(2) C(3) C(4) 110.8(3) . . . yes C(2) C(3) C(8) 111.2(2) . . . yes C(4) C(3) C(8) 114.2(3) . . . yes C(3) C(4) C(5) 113.2(3) . . . yes C(3) C(4) H(1) 105(1) . . . no C(3) C(4) H(2) 106(1) . . . no C(5) C(4) H(1) 111(1) . . . no C(5) C(4) H(2) 113(1) . . . no H(1) C(4) H(2) 106(2) . . . no C(4) C(5) C(6) 127.8(4) . . . yes C(4) C(5) H(3) 112(2) . . . no C(6) C(5) H(3) 119(2) . . . no C(5) C(6) C(7) 126.9(4) . . . yes C(5) C(6) H(4) 112(2) . . . no C(7) C(6) H(4) 120(2) . . . no C(6) C(7) H(5) 112.5 . . . no C(6) C(7) H(6) 112.4 . . . no C(6) C(7) H(7) 112.9 . . . no H(5) C(7) H(6) 105.6 . . . no H(5) C(7) H(7) 107.1 . . . no H(6) C(7) H(7) 105.8 . . . no C(3) C(8) C(9) 120.5(3) . . . yes C(3) C(8) C(13) 120.5(3) . . . yes C(9) C(8) C(13) 119.0(3) . . . yes C(8) C(9) C(10) 119.0(4) . . . yes C(8) C(9) H(8) 122(2) . . . no C(10) C(9) H(8) 118(2) . . . no C(9) C(10) C(11) 121.9(4) . . . yes C(9) C(10) H(9) 120(3) . . . no C(11) C(10) H(9) 117(3) . . . no C(10) C(11) C(12) 118.9(4) . . . yes C(10) C(11) H(10) 122(2) . . . no C(12) C(11) H(10) 119(2) . . . no C(11) C(12) C(13) 121.3(4) . . . yes C(11) C(12) H(11) 120(2) . . . no C(13) C(12) H(11) 118(2) . . . no C(8) C(13) C(12) 120.0(4) . . . yes C(8) C(13) H(12) 118(2) . . . no C(12) C(13) H(12) 121(2) . . . no S(1) C(14) C(15) 120.3(3) . . . yes S(1) C(14) C(19) 119.9(3) . . . yes C(15) C(14) C(19) 119.8(3) . . . yes C(14) C(15) C(16) 119.8(4) . . . yes C(14) C(15) H(13) 117(2) . . . no C(16) C(15) H(13) 122(2) . . . no C(15) C(16) C(17) 121.4(4) . . . yes C(15) C(16) H(14) 123(2) . . . no C(17) C(16) H(14) 114(2) . . . no C(16) C(17) C(18) 117.4(3) . . . yes C(16) C(17) C(20) 120.3(4) . . . yes C(18) C(17) C(20) 122.3(4) . . . yes C(17) C(18) C(19) 122.2(4) . . . yes C(17) C(18) H(15) 121(2) . . . no C(19) C(18) H(15) 116(2) . . . no C(14) C(19) C(18) 119.3(4) . . . yes C(14) C(19) H(16) 121(2) . . . no C(18) C(19) H(16) 119(2) . . . no C(17) C(20) H(17) 112(3) . . . no C(17) C(20) H(18) 112(3) . . . no C(17) C(20) H(19) 106(4) . . . no H(17) C(20) H(18) 107(4) . . . no H(17) C(20) H(19) 115(5) . . . no H(18) C(20) H(19) 102(5) . . . no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S(1) N(1) C(1) O(1) -0.2(4) . . . . yes S(1) N(1) C(1) O(3) -178.9(2) . . . . yes S(1) N(1) C(2) O(2) 2.4(5) . . . . yes S(1) N(1) C(2) C(3) -178.6(2) . . . . yes S(1) C(14) C(15) C(16) -179.4(3) . . . . yes S(1) C(14) C(19) C(18) -179.9(3) . . . . yes O(1) C(1) O(3) C(3) -178.6(3) . . . . yes O(1) C(1) N(1) C(2) 172.6(3) . . . . yes O(2) C(2) N(1) C(1) -170.0(3) . . . . yes O(2) C(2) C(3) O(3) 170.5(3) . . . . yes O(2) C(2) C(3) C(4) 55.2(4) . . . . yes O(2) C(2) C(3) C(8) -73.1(4) . . . . yes O(3) C(1) N(1) C(2) -6.0(3) . . . . yes O(3) C(3) C(2) N(1) -8.5(3) . . . . yes O(3) C(3) C(4) C(5) -55.1(4) . . . . yes O(3) C(3) C(8) C(9) -9.8(4) . . . . yes O(3) C(3) C(8) C(13) 170.5(3) . . . . yes O(4) S(1) N(1) C(1) -163.4(2) . . . . yes O(4) S(1) N(1) C(2) 25.1(3) . . . . yes O(4) S(1) C(14) C(15) -27.4(3) . . . . yes O(4) S(1) C(14) C(19) 152.3(3) . . . . yes O(5) S(1) N(1) C(1) -35.2(3) . . . . yes O(5) S(1) N(1) C(2) 153.4(3) . . . . yes O(5) S(1) C(14) C(15) -165.2(3) . . . . yes O(5) S(1) C(14) C(19) 14.5(4) . . . . yes N(1) S(1) C(14) C(15) 82.2(3) . . . . yes N(1) S(1) C(14) C(19) -98.2(3) . . . . yes N(1) C(1) O(3) C(3) 0.0(3) . . . . yes N(1) C(2) C(3) C(4) -123.9(3) . . . . yes N(1) C(2) C(3) C(8) 107.9(3) . . . . yes C(1) O(3) C(3) C(2) 5.3(3) . . . . yes C(1) O(3) C(3) C(4) 122.7(3) . . . . yes C(1) O(3) C(3) C(8) -112.9(3) . . . . yes C(1) N(1) S(1) C(14) 81.1(2) . . . . yes C(1) N(1) C(2) C(3) 9.0(3) . . . . yes C(2) N(1) S(1) C(14) -90.4(3) . . . . yes C(2) C(3) C(4) C(5) 57.3(4) . . . . yes C(2) C(3) C(8) C(9) -122.9(3) . . . . yes C(2) C(3) C(8) C(13) 57.5(4) . . . . yes C(3) C(4) C(5) C(6) -109.7(5) . . . . yes C(3) C(8) C(9) C(10) 179.4(4) . . . . yes C(3) C(8) C(13) C(12) -179.1(4) . . . . yes C(4) C(3) C(8) C(9) 110.7(4) . . . . yes C(4) C(3) C(8) C(13) -68.9(4) . . . . yes C(4) C(5) C(6) C(7) -1.4(7) . . . . yes C(5) C(4) C(3) C(8) -176.1(3) . . . . yes C(8) C(9) C(10) C(11) -0.2(7) . . . . yes C(8) C(13) C(12) C(11) -0.4(7) . . . . yes C(9) C(8) C(13) C(12) 1.3(6) . . . . yes C(9) C(10) C(11) C(12) 1.0(7) . . . . yes C(10) C(9) C(8) C(13) -1.0(6) . . . . yes C(10) C(11) C(12) C(13) -0.8(7) . . . . yes C(14) C(15) C(16) C(17) -1.3(7) . . . . yes C(14) C(19) C(18) C(17) 0.0(7) . . . . yes C(15) C(14) C(19) C(18) -0.2(6) . . . . yes C(15) C(16) C(17) C(18) 1.1(6) . . . . yes C(15) C(16) C(17) C(20) -178.7(4) . . . . yes C(16) C(15) C(14) C(19) 0.9(6) . . . . yes C(16) C(17) C(18) C(19) -0.4(6) . . . . yes C(19) C(18) C(17) C(20) 179.4(4) . . . . yes C(19) C(18) C(17) C(20) 179.4(4) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S(1) H(4) 3.44(5) . 1_556 ? O(1) H(16) 2.75(4) . 2_666 ? O(1) H(19) 2.89(6) . 2_665 ? O(1) H(17) 2.92(6) . 1_656 ? O(1) H(15) 2.98(4) . 2_666 ? O(1) H(14) 3.00(4) . 1_656 ? O(1) C(19) 3.274(5) . 2_666 ? O(1) H(4) 3.31(5) . 1_556 ? O(1) H(18) 3.39(5) . 2_665 ? O(1) C(18) 3.429(5) . 2_666 ? O(1) C(20) 3.439(6) . 2_665 ? O(1) H(17) 3.52(6) . 2_665 ? O(2) H(11) 2.98(4) . 2_656 ? O(2) H(9) 3.31(4) . 1_454 ? O(2) H(10) 3.45(3) . 2_656 ? O(2) C(12) 3.520(5) . 2_656 ? O(3) H(14) 3.07(4) . 1_656 ? O(3) O(4) 3.294(3) . 1_655 ? O(4) C(4) 3.289(5) . 1_455 ? O(4) H(11) 3.32(4) . 2_656 ? O(4) H(3) 3.37(4) . 1_455 ? O(4) H(8) 3.49(3) . 1_455 ? O(5) H(4) 2.67(5) . 1_556 ? O(5) H(15) 3.08(4) . 2_666 ? O(5) H(16) 3.12(4) . 2_666 ? O(5) H(19) 3.15(6) . 1_556 ? O(5) H(14) 3.24(4) . 1_556 ? O(5) H(17) 3.27(6) . 1_556 ? O(5) C(20) 3.452(6) . 1_556 ? O(5) C(16) 3.522(5) . 1_556 ? N(1) H(4) 3.31(5) . 1_556 ? C(1) H(4) 3.29(5) . 1_556 ? C(1) H(14) 3.31(4) . 1_656 ? C(1) H(19) 3.43(6) . 2_665 ? C(4) H(10) 3.25(4) . 2_756 ? C(5) H(13) 3.47(4) . 1_655 ? C(7) H(11) 3.28(4) . 2_655 ? C(7) H(12) 3.49(4) . 2_655 ? C(9) H(13) 3.48(4) . 1_656 ? C(10) H(10) 3.22(4) . 2_757 ? C(10) H(13) 3.58(4) . 1_656 ? C(11) H(10) 3.19(4) . 2_757 ? C(11) H(1) 3.41(3) . 2_756 ? C(11) H(2) 3.56(3) . 2_756 ? C(11) H(9) 3.57(4) . 2_757 ? C(14) H(18) 3.39(5) . 2_565 ? C(15) H(8) 3.32(4) . 1_454 ? C(15) H(3) 3.32(4) . 1_455 ? C(16) H(8) 3.24(4) . 1_454 ? C(18) H(19) 3.49(6) . 2_665 ? C(18) H(18) 3.57(5) . 2_565 ? C(19) H(19) 3.31(6) . 2_665 ? C(19) H(18) 3.36(5) . 2_565 ? C(19) H(16) 3.42(4) . 2_666 ? C(20) H(17) 3.22(6) . 2_564 ? H(1) H(10) 2.70(5) . 2_756 ? H(1) H(13) 3.32(5) . 1_655 ? H(1) H(9) 3.42(5) . 1_554 ? H(1) H(11) 3.50(5) . 2_756 ? H(2) H(10) 2.89(5) . 2_756 ? H(3) H(18) 2.89(6) . 2_665 ? H(3) H(13) 3.10(5) . 1_655 ? H(3) H(15) 3.48(6) . 2_665 ? H(3) H(19) 3.51(7) . 2_665 ? H(4) H(15) 2.70(6) . 2_665 ? H(8) H(14) 2.66(5) . 1_656 ? H(8) H(13) 2.78(5) . 1_656 ? H(9) H(10) 2.73(6) . 2_757 ? H(9) H(13) 3.09(6) . 1_656 ? H(10) H(10) 2.69(7) . 2_757 ? H(11) H(12) 3.38(6) . 2_656 ? H(15) H(19) 3.49(7) . 2_665 ? H(16) H(16) 2.58(8) . 2_666 ? H(16) H(19) 3.17(7) . 2_665 ? H(16) H(19) 3.57(8) . 1_556 ? H(17) H(17) 2.6(1) . 2_564 ? H(17) H(18) 3.21(8) . 2_564 ? H(17) H(19) 3.37(9) . 2_564 ? #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment 'CIF_6d.cif' #------------------------------------------------------------------------------ data_n488-060131_ _database_code_depnum_ccdc_archive 'CCDC 729636' #TrackingRef 'CIF_6d.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C15 H16 I N O2 ' _chemical_formula_moiety 'C15 H16 I N O2 ' _chemical_formula_weight 369.20 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21 ' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,1/2+z 1/2-x,y,1/2+z 1/2+x,-y,z _cell_length_a 15.4263(6) _cell_length_b 7.5195(3) _cell_length_c 13.4786(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1563.49(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11291 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.150 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 2.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.527 _exptl_absorpt_correction_T_max 0.736 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 14655 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 1.8904 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.8904 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3537 _reflns_number_gt 2803 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1144 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 2803 _refine_ls_number_parameters 185 _refine_ls_goodness_of_fit_ref 1.645 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0148 _refine_diff_density_max 1.61 _refine_diff_density_min -0.41 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983), 2803 Reflections' _refine_ls_abs_structure_Flack 0.09(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.474 1.812 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I(1) I 0.13957(2) 1.09132(4) 0.171(2) 0.06855(10) Uani 1.00 d . . . O(1) O 0.5135(2) 1.0756(4) 0.481(2) 0.064(1) Uani 1.00 d . . . O(2) O 0.5609(2) 0.8133(4) 0.535(2) 0.070(1) Uani 1.00 d . . . N(1) N 0.4432(2) 0.8137(4) 0.440(2) 0.0500(9) Uani 1.00 d . . . C(1) C 0.5062(3) 0.9162(6) 0.484(2) 0.052(1) Uani 1.00 d . . . C(2) C 0.5294(4) 0.6247(6) 0.535(2) 0.068(1) Uani 1.00 d . . . C(3) C 0.4558(4) 0.6312(6) 0.459(2) 0.063(1) Uani 1.00 d . . . C(4) C 0.6057(4) 0.5118(7) 0.502(2) 0.072(2) Uani 1.00 d . . . C(5) C 0.6332(5) 0.561(1) 0.400(2) 0.083(2) Uani 1.00 d . . . C(6) C 0.6784(6) 0.522(1) 0.575(2) 0.115(3) Uani 1.00 d . . . C(7) C 0.7041(7) 0.399(1) 0.634(2) 0.129(4) Uani 1.00 d . . . C(8) C 0.4967(5) 0.5787(9) 0.643(2) 0.086(2) Uani 1.00 d . . . C(9) C 0.4110(5) 0.4969(7) 0.423(2) 0.078(2) Uani 1.00 d . . . C(10) C 0.3746(3) 0.8849(6) 0.382(2) 0.051(1) Uani 1.00 d . . . C(11) C 0.3915(4) 0.9806(8) 0.298(2) 0.067(2) Uani 1.00 d . . . C(12) C 0.3243(4) 1.0418(8) 0.237(2) 0.069(2) Uani 1.00 d . . . C(13) C 0.2417(3) 1.0104(5) 0.265(2) 0.051(1) Uani 1.00 d . . . C(14) C 0.2209(3) 0.9205(6) 0.352(2) 0.055(1) Uani 1.00 d . . . C(15) C 0.2906(3) 0.8575(7) 0.410(2) 0.056(1) Uani 1.00 d . . . H(1) H 0.5848 0.3715 0.4972 0.0865 Uiso 1.00 calc . . . H(2) H 0.5745 0.5766 0.3505 0.0998 Uiso 1.00 calc . . . H(3) H 0.6676 0.6895 0.3994 0.0998 Uiso 1.00 calc . . . H(4) H 0.6750 0.4589 0.3658 0.0998 Uiso 1.00 calc . . . H(5) H 0.7121 0.6464 0.5764 0.1410 Uiso 1.00 calc . . . H(6) H 0.7554 0.4168 0.6812 0.1418 Uiso 1.00 calc . . . H(7) H 0.6712 0.2711 0.6298 0.1418 Uiso 1.00 calc . . . H(8) H 0.5520 0.5943 0.6926 0.1044 Uiso 1.00 calc . . . H(9) H 0.4735 0.4417 0.6434 0.1044 Uiso 1.00 calc . . . H(10) H 0.4450 0.6709 0.6621 0.1044 Uiso 1.00 calc . . . H(11) H 0.4249 0.3642 0.4436 0.0962 Uiso 1.00 calc . . . H(12) H 0.3604 0.5193 0.3687 0.0962 Uiso 1.00 calc . . . H(13) H 0.448(3) 1.000(8) 0.281(4) 0.05(1) Uiso 1.00 calc . . . H(14) H 0.3468 1.0846 0.1705 0.1136 Uiso 1.00 calc . . . H(15) H 0.158(3) 0.907(5) 0.383(4) 0.04(1) Uiso 1.00 calc . . . H(16) H 0.281(6) 0.79(1) 0.473(7) 0.116(10) Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.0582(2) 0.0691(2) 0.0784(2) 0.0078(1) -0.0176(2) 0.0000(3) O(1) 0.059(2) 0.036(1) 0.098(3) -0.005(1) -0.006(2) -0.002(2) O(2) 0.066(2) 0.036(2) 0.109(3) -0.004(1) -0.034(2) 0.006(2) N(1) 0.043(2) 0.035(2) 0.072(2) 0.000(1) -0.007(1) 0.004(2) C(1) 0.052(2) 0.038(2) 0.066(3) -0.006(1) 0.000(2) -0.002(2) C(2) 0.078(3) 0.038(2) 0.088(3) -0.007(2) -0.026(2) 0.007(2) C(3) 0.069(3) 0.039(2) 0.080(3) -0.001(2) -0.014(2) 0.011(2) C(4) 0.091(4) 0.042(3) 0.083(3) 0.009(2) -0.008(2) 0.014(3) C(5) 0.077(4) 0.089(5) 0.085(4) 0.033(4) 0.015(3) 0.006(3) C(6) 0.088(5) 0.104(5) 0.153(7) 0.035(5) -0.061(5) -0.027(4) C(7) 0.110(6) 0.179(9) 0.098(5) 0.073(6) -0.021(4) 0.015(5) C(8) 0.079(4) 0.080(4) 0.097(4) -0.011(3) 0.000(3) 0.020(3) C(9) 0.083(4) 0.042(3) 0.110(5) -0.009(2) -0.022(3) -0.004(3) C(10) 0.043(2) 0.040(2) 0.069(3) 0.003(1) -0.003(1) 0.005(2) C(11) 0.043(2) 0.080(4) 0.079(3) -0.007(2) 0.009(2) 0.027(3) C(12) 0.054(2) 0.080(4) 0.075(3) -0.002(2) 0.001(2) 0.030(3) C(13) 0.051(2) 0.036(2) 0.065(2) 0.003(2) -0.003(1) 0.001(2) C(14) 0.042(2) 0.056(3) 0.069(3) -0.007(2) 0.004(2) 0.005(2) C(15) 0.049(2) 0.057(3) 0.061(3) -0.006(2) 0.003(2) 0.012(2) #------------------------------------------------------------------------------ _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I(1) C(13) 2.116(6) . . yes O(1) C(1) 1.205(6) . . yes O(2) C(1) 1.331(8) . . yes O(2) C(2) 1.499(8) . . yes N(1) C(1) 1.376(8) . . yes N(1) C(3) 1.410(8) . . yes N(1) C(10) 1.424(8) . . yes C(2) C(3) 1.531(10) . . yes C(2) C(4) 1.52(1) . . yes C(2) C(8) 1.57(1) . . yes C(3) C(9) 1.32(1) . . yes C(4) C(5) 1.49(1) . . yes C(4) C(6) 1.49(1) . . yes C(6) C(7) 1.29(2) . . yes C(10) C(11) 1.37(1) . . yes C(10) C(15) 1.367(9) . . yes C(11) C(12) 1.39(1) . . yes C(12) C(13) 1.349(9) . . yes C(13) C(14) 1.386(9) . . yes C(14) C(15) 1.412(9) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) O(2) C(2) 110.4(4) . . . yes C(1) N(1) C(3) 111.6(5) . . . yes C(1) N(1) C(10) 123.6(5) . . . yes C(3) N(1) C(10) 124.8(5) . . . yes O(1) C(1) O(2) 122.6(6) . . . yes O(1) C(1) N(1) 127.3(6) . . . yes O(2) C(1) N(1) 110.1(4) . . . yes O(2) C(2) C(3) 101.8(5) . . . yes O(2) C(2) C(4) 106.0(6) . . . yes O(2) C(2) C(8) 108.6(6) . . . yes C(3) C(2) C(4) 113.3(7) . . . yes C(3) C(2) C(8) 112.7(7) . . . yes C(4) C(2) C(8) 113.5(6) . . . yes N(1) C(3) C(2) 104.9(5) . . . yes N(1) C(3) C(9) 127.2(7) . . . yes C(2) C(3) C(9) 127.9(6) . . . yes C(2) C(4) C(5) 110.8(6) . . . yes C(2) C(4) C(6) 111.2(7) . . . yes C(5) C(4) C(6) 112.2(10) . . . yes C(4) C(6) C(7) 127(1) . . . yes N(1) C(10) C(11) 121.0(6) . . . yes N(1) C(10) C(15) 119.5(6) . . . yes C(11) C(10) C(15) 119.5(6) . . . yes C(10) C(11) C(12) 120.9(6) . . . yes C(11) C(12) C(13) 118.9(6) . . . yes I(1) C(13) C(12) 119.1(5) . . . yes I(1) C(13) C(14) 118.4(4) . . . yes C(12) C(13) C(14) 122.4(6) . . . yes C(13) C(14) C(15) 117.1(5) . . . yes C(10) C(15) C(14) 121.0(6) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I(1) C(13) C(12) C(11) -176.9(6) . . . . yes I(1) C(13) C(14) C(15) 175.8(5) . . . . yes O(1) C(1) O(2) C(2) 173.3(7) . . . . yes O(1) C(1) N(1) C(3) 179.3(7) . . . . yes O(1) C(1) N(1) C(10) 0(1) . . . . yes O(2) C(1) N(1) C(3) -0.9(8) . . . . yes O(2) C(1) N(1) C(10) 179.5(6) . . . . yes O(2) C(2) C(3) N(1) -10.4(8) . . . . yes O(2) C(2) C(3) C(9) 172.3(9) . . . . yes O(2) C(2) C(4) C(5) -61.1(9) . . . . yes O(2) C(2) C(4) C(6) 64.3(9) . . . . yes N(1) C(1) O(2) C(2) -6.5(8) . . . . yes N(1) C(3) C(2) C(4) -123.8(6) . . . . yes N(1) C(3) C(2) C(8) 105.7(7) . . . . yes N(1) C(10) C(11) C(12) 176.4(7) . . . . yes N(1) C(10) C(15) C(14) -177.6(6) . . . . yes C(1) O(2) C(2) C(3) 10.5(8) . . . . yes C(1) O(2) C(2) C(4) 129.3(6) . . . . yes C(1) O(2) C(2) C(8) -108.5(7) . . . . yes C(1) N(1) C(3) C(2) 7.5(8) . . . . yes C(1) N(1) C(3) C(9) -175.1(9) . . . . yes C(1) N(1) C(10) C(11) 60.2(9) . . . . yes C(1) N(1) C(10) C(15) -119.7(7) . . . . yes C(2) C(3) N(1) C(10) -172.8(6) . . . . yes C(2) C(4) C(6) C(7) 108(1) . . . . yes C(3) N(1) C(10) C(11) -119.4(8) . . . . yes C(3) N(1) C(10) C(15) 60.7(9) . . . . yes C(3) C(2) C(4) C(5) 49.7(9) . . . . yes C(3) C(2) C(4) C(6) 175.2(8) . . . . yes C(4) C(2) C(3) C(9) 58(1) . . . . yes C(5) C(4) C(2) C(8) 179.8(8) . . . . yes C(5) C(4) C(6) C(7) -126(1) . . . . yes C(6) C(4) C(2) C(8) -54(1) . . . . yes C(8) C(2) C(3) C(9) -71(1) . . . . yes C(9) C(3) N(1) C(10) 4(1) . . . . yes C(10) C(11) C(12) C(13) 2(1) . . . . yes C(10) C(15) C(14) C(13) 0.1(9) . . . . yes C(11) C(10) C(15) C(14) 2.5(10) . . . . yes C(11) C(12) C(13) C(14) 0(1) . . . . yes C(12) C(11) C(10) C(15) -3(1) . . . . yes C(12) C(13) C(14) C(15) -1.7(9) . . . . yes C(12) C(13) C(14) C(15) -1.7(9) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag I(1) O(1) 3.483(6) . 3_554 ? O(1) C(4) 3.587(9) . 1_565 ? O(2) C(12) 3.435(8) . 2_675 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ # Attachment 'CIF_8.cif' data__050212 _database_code_depnum_ccdc_archive 'CCDC 729637' #TrackingRef 'CIF_8.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H19 N O5 S ' _chemical_formula_moiety 'C20 H19 N O5 S ' _chemical_formula_weight 385.43 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,+Z #------------------------------------------------------------------------------ _cell_length_a 14.0275(19) _cell_length_b 7.7306(12) _cell_length_c 18.2940(18) _cell_angle_alpha 90.0000 _cell_angle_beta 103.650(8) _cell_angle_gamma 90.0000 _cell_volume 1927.8(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.9 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 296.1 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808.00 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.905 _exptl_absorpt_correction_T_max 0.952 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 5841 _diffrn_reflns_av_R_equivalents 0.101 _diffrn_reflns_theta_max 30.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -0.05 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5619 _reflns_number_gt 2757 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.0556 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2764 _refine_ls_number_parameters 302 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 3.5832 1.0586 2.9377 ; _refine_ls_shift/su_max 0.0006 _refine_diff_density_max 0.48 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S(1) S 0.55107(5) -0.07661(9) 0.67037(4) 0.04184(15) Uani 1.00 1 d . . . O(1) O 0.54025(17) -0.1415(2) 0.83866(11) 0.0549(6) Uani 1.00 1 d . . . O(2) O 0.57343(13) 0.1356(2) 0.86574(9) 0.0379(4) Uani 1.00 1 d . . . O(4) O 0.55833(17) -0.2502(2) 0.69701(11) 0.0602(5) Uani 1.00 1 d . . . O(5) O 0.59426(16) 0.3162(2) 0.69496(10) 0.0519(5) Uani 1.00 1 d . . . O(6) O 0.61357(15) -0.0143(3) 0.62577(11) 0.0573(5) Uani 1.00 1 d . . . N(1) N 0.57414(15) 0.0507(2) 0.74926(11) 0.0360(4) Uani 1.00 1 d . . . C(8) C 0.56016(19) -0.0024(3) 0.82000(14) 0.0378(6) Uani 1.00 1 d . . . C(9) C 0.58901(17) 0.2945(2) 0.82702(12) 0.0336(5) Uani 1.00 1 d . . . C(10) C 0.42898(18) -0.0274(3) 0.62838(13) 0.0360(5) Uani 1.00 1 d . . . C(11) C 0.68740(17) 0.3741(3) 0.86465(13) 0.0350(5) Uani 1.00 1 d . . . C(12) C 0.58743(17) 0.2316(3) 0.74766(13) 0.0355(5) Uani 1.00 1 d . . . C(13) C 0.50121(18) 0.4175(3) 0.82507(14) 0.0396(6) Uani 1.00 1 d . . . C(14) C 0.4073(2) 0.0736(4) 0.56435(15) 0.0500(7) Uani 1.00 1 d . . . C(15) C 0.7454(2) 0.3067(3) 0.93088(15) 0.0459(6) Uani 1.00 1 d . . . C(16) C 0.4064(2) 0.3372(4) 0.78397(19) 0.0516(8) Uani 1.00 1 d . . . C(17) C 0.8630(2) 0.5320(4) 0.93415(18) 0.0563(8) Uani 1.00 1 d . . . C(18) C 0.3548(2) -0.0926(3) 0.65929(16) 0.0475(7) Uani 1.00 1 d . . . C(19) C 0.8333(2) 0.3885(4) 0.96539(17) 0.0547(8) Uani 1.00 1 d . . . C(20) C 0.7185(2) 0.5210(3) 0.83359(16) 0.0473(7) Uani 1.00 1 d . . . C(21) C 0.2350(2) 0.0465(4) 0.56069(16) 0.0508(7) Uani 1.00 1 d . . . C(22) C 0.4976(2) 0.4708(4) 0.90492(17) 0.0548(8) Uani 1.00 1 d . . . C(23) C 0.2588(2) -0.0533(4) 0.62539(17) 0.0523(8) Uani 1.00 1 d . . . C(24) C 0.8065(2) 0.5982(4) 0.86862(19) 0.0563(8) Uani 1.00 1 d . . . C(25) C 0.3096(2) 0.1084(4) 0.53052(18) 0.0565(8) Uani 1.00 1 d . . . C(26) C 0.1293(2) 0.0838(6) 0.5228(2) 0.0796(11) Uani 1.00 1 d . . . C(27) C 0.3566(2) 0.3863(5) 0.7175(2) 0.0748(11) Uani 1.00 1 d . . . H(1) H 0.4576 0.3909 0.9236 0.068 Uiso 1.00 1 c R . . H(2) H 0.4707 0.5837 0.9045 0.068 Uiso 1.00 1 c R . . H(3) H 0.5620 0.4694 0.9363 0.068 Uiso 1.00 1 c R . . H(4) H 0.1052 -0.0032 0.4864 0.093 Uiso 1.00 1 c R . . H(5) H 0.1247 0.1935 0.4988 0.093 Uiso 1.00 1 c R . . H(6) H 0.0915 0.0844 0.5596 0.093 Uiso 1.00 1 c R . . H(7) H 0.922(2) 0.593(4) 0.958(2) 0.071(10) Uiso 1.00 1 c . . . H(8) H 0.826(2) 0.694(4) 0.845(2) 0.076(11) Uiso 1.00 1 c . . . H(9) H 0.679(2) 0.567(3) 0.7880(16) 0.042(7) Uiso 1.00 1 c . . . H(10) H 0.728(2) 0.208(4) 0.9513(16) 0.049(8) Uiso 1.00 1 c . . . H(11) H 0.868(2) 0.342(4) 1.010(2) 0.068(10) Uiso 1.00 1 c . . . H(12) H 0.517(2) 0.509(3) 0.7951(16) 0.044(7) Uiso 1.00 1 c . . . H(13) H 0.382(2) 0.250(5) 0.8060(18) 0.069(10) Uiso 1.00 1 c . . . H(14) H 0.298(3) 0.326(5) 0.697(2) 0.109(16) Uiso 1.00 1 c . . . H(15) H 0.390(2) 0.469(4) 0.688(2) 0.065(10) Uiso 1.00 1 c . . . H(16) H 0.372(2) -0.162(4) 0.7065(19) 0.069(10) Uiso 1.00 1 c . . . H(17) H 0.213(2) -0.098(4) 0.647(2) 0.072(10) Uiso 1.00 1 c . . . H(18) H 0.460(2) 0.123(4) 0.5443(19) 0.067(9) Uiso 1.00 1 c . . . H(19) H 0.289(3) 0.171(5) 0.487(2) 0.089(12) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0429(3) 0.0429(3) 0.0376(3) 0.0084(2) 0.0053(2) -0.0089(2) O(1) 0.0768(15) 0.0356(9) 0.0531(11) -0.0058(9) 0.0170(10) 0.0024(8) O(2) 0.0505(10) 0.0315(7) 0.0318(8) -0.0040(7) 0.0099(7) 0.0003(6) O(4) 0.0775(15) 0.0404(9) 0.0543(10) 0.0202(10) -0.0013(10) -0.0068(8) O(5) 0.0718(13) 0.0489(10) 0.0363(9) -0.0070(9) 0.0153(8) 0.0039(7) O(6) 0.0452(10) 0.0809(14) 0.0490(10) 0.0024(10) 0.0173(8) -0.0167(10) N(1) 0.0415(10) 0.0334(10) 0.0314(9) 0.0007(8) 0.0053(7) -0.0046(7) C(8) 0.0424(12) 0.0296(11) 0.0394(12) 0.0017(9) 0.0053(10) 0.0022(9) C(9) 0.0391(11) 0.0300(10) 0.0311(10) -0.0035(9) 0.0072(8) 0.0012(8) C(10) 0.0388(11) 0.0357(11) 0.0315(10) 0.0008(9) 0.0043(9) -0.0035(8) C(11) 0.0354(11) 0.0367(11) 0.0328(11) -0.0008(9) 0.0075(9) -0.0038(8) C(12) 0.0329(11) 0.0379(11) 0.0343(10) -0.0012(9) 0.0048(8) -0.0022(9) C(13) 0.0402(12) 0.0350(11) 0.0441(12) 0.0007(10) 0.0108(10) -0.0008(10) C(14) 0.0488(14) 0.0586(16) 0.0429(13) 0.0025(14) 0.0118(11) 0.0128(12) C(15) 0.0476(14) 0.0490(14) 0.0376(12) -0.0001(12) 0.0029(10) 0.0028(10) C(16) 0.0413(14) 0.0491(16) 0.0646(18) -0.0004(12) 0.0132(13) -0.0043(13) C(17) 0.0398(14) 0.0655(19) 0.0584(17) -0.0063(13) 0.0014(12) -0.0172(14) C(18) 0.0533(15) 0.0492(15) 0.0400(12) -0.0078(12) 0.0109(11) 0.0032(11) C(19) 0.0452(15) 0.0685(19) 0.0442(15) 0.0063(13) -0.0016(12) -0.0059(13) C(20) 0.0444(13) 0.0476(14) 0.0476(14) -0.0087(12) 0.0062(11) 0.0024(11) C(21) 0.0416(13) 0.0640(18) 0.0426(13) 0.0058(13) 0.0020(10) -0.0114(12) C(22) 0.0609(17) 0.0525(16) 0.0550(16) 0.0038(13) 0.0216(14) -0.0115(12) C(23) 0.0440(14) 0.0623(18) 0.0529(16) -0.0113(13) 0.0161(12) -0.0065(13) C(24) 0.0502(15) 0.0534(17) 0.0639(18) -0.0173(13) 0.0105(13) -0.0057(14) C(25) 0.0574(17) 0.0630(19) 0.0457(15) 0.0109(14) 0.0050(12) 0.0141(13) C(26) 0.0493(17) 0.109(3) 0.073(2) 0.014(2) -0.0011(16) -0.016(2) C(27) 0.0520(19) 0.080(2) 0.082(2) 0.0039(18) -0.0067(18) -0.008(2) #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S(1) O(4) 1.423(2) yes . . S(1) O(6) 1.416(2) yes . . S(1) N(1) 1.713(2) yes . . S(1) C(10) 1.745(2) yes . . O(1) C(8) 1.181(3) yes . . O(2) C(8) 1.342(2) yes . . O(2) C(9) 1.460(2) yes . . O(5) C(12) 1.188(3) yes . . N(1) C(8) 1.415(3) yes . . N(1) C(12) 1.412(3) yes . . C(9) C(11) 1.520(3) yes . . C(9) C(12) 1.526(3) yes . . C(9) C(13) 1.550(3) yes . . C(10) C(14) 1.381(3) yes . . C(10) C(18) 1.391(4) yes . . C(11) C(15) 1.392(3) yes . . C(11) C(20) 1.386(3) yes . . C(13) C(16) 1.499(3) yes . . C(13) C(22) 1.530(4) yes . . C(14) C(25) 1.390(4) yes . . C(15) C(19) 1.396(4) yes . . C(16) C(27) 1.308(5) yes . . C(17) C(19) 1.358(4) yes . . C(17) C(24) 1.371(4) yes . . C(18) C(23) 1.377(4) yes . . C(20) C(24) 1.385(4) yes . . C(21) C(23) 1.386(4) yes . . C(21) C(25) 1.380(4) yes . . C(21) C(26) 1.508(4) yes . . C(13) H(12) 0.95(3) no . . C(14) H(18) 0.97(4) no . . C(15) H(10) 0.90(3) no . . C(16) H(13) 0.89(3) no . . C(17) H(7) 0.96(3) no . . C(18) H(16) 1.00(3) no . . C(19) H(11) 0.92(3) no . . C(20) H(9) 0.96(2) no . . C(22) H(1) 0.950 no . . C(22) H(2) 0.950 no . . C(22) H(3) 0.950 no . . C(23) H(17) 0.90(4) no . . C(24) H(8) 0.93(3) no . . C(25) H(19) 0.92(3) no . . C(26) H(4) 0.950 no . . C(26) H(5) 0.950 no . . C(26) H(6) 0.950 no . . C(27) H(14) 0.94(4) no . . C(27) H(15) 1.02(3) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(4) S(1) O(6) 120.95(14) yes . . . O(4) S(1) N(1) 105.61(10) yes . . . O(4) S(1) C(10) 109.85(12) yes . . . O(6) S(1) N(1) 105.69(11) yes . . . O(6) S(1) C(10) 110.42(12) yes . . . N(1) S(1) C(10) 102.49(11) yes . . . C(8) O(2) C(9) 112.41(18) yes . . . S(1) N(1) C(8) 124.37(15) yes . . . S(1) N(1) C(12) 123.43(16) yes . . . C(8) N(1) C(12) 110.72(19) yes . . . O(1) C(8) O(2) 123.5(2) yes . . . O(1) C(8) N(1) 128.4(2) yes . . . O(2) C(8) N(1) 108.10(19) yes . . . O(2) C(9) C(11) 110.17(16) yes . . . O(2) C(9) C(12) 102.91(17) yes . . . O(2) C(9) C(13) 108.6(2) yes . . . C(11) C(9) C(12) 111.6(2) yes . . . C(11) C(9) C(13) 113.20(18) yes . . . C(12) C(9) C(13) 109.91(17) yes . . . S(1) C(10) C(14) 119.6(2) yes . . . S(1) C(10) C(18) 119.53(18) yes . . . C(14) C(10) C(18) 120.9(2) yes . . . C(9) C(11) C(15) 121.7(2) yes . . . C(9) C(11) C(20) 119.11(19) yes . . . C(15) C(11) C(20) 119.2(2) yes . . . O(5) C(12) N(1) 126.8(2) yes . . . O(5) C(12) C(9) 127.7(2) yes . . . N(1) C(12) C(9) 105.55(19) yes . . . C(9) C(13) C(16) 111.3(2) yes . . . C(9) C(13) C(22) 110.40(19) yes . . . C(16) C(13) C(22) 111.4(2) yes . . . C(10) C(14) C(25) 118.9(2) yes . . . C(11) C(15) C(19) 119.8(2) yes . . . C(13) C(16) C(27) 124.2(3) yes . . . C(19) C(17) C(24) 120.1(2) yes . . . C(10) C(18) C(23) 118.9(2) yes . . . C(15) C(19) C(17) 120.4(2) yes . . . C(11) C(20) C(24) 119.8(2) yes . . . C(23) C(21) C(25) 118.8(2) yes . . . C(23) C(21) C(26) 120.8(3) yes . . . C(25) C(21) C(26) 120.4(2) yes . . . C(18) C(23) C(21) 121.4(3) yes . . . C(17) C(24) C(20) 120.8(3) yes . . . C(14) C(25) C(21) 121.1(2) yes . . . C(9) C(13) H(12) 100.4(18) no . . . C(16) C(13) H(12) 108.3(16) no . . . C(22) C(13) H(12) 114.5(18) no . . . C(10) C(14) H(18) 120.6(19) no . . . C(25) C(14) H(18) 120.4(19) no . . . C(11) C(15) H(10) 121.1(16) no . . . C(19) C(15) H(10) 119.1(17) no . . . C(13) C(16) H(13) 118(2) no . . . C(27) C(16) H(13) 117.4(19) no . . . C(19) C(17) H(7) 122(2) no . . . C(24) C(17) H(7) 118(2) no . . . C(10) C(18) H(16) 120(2) no . . . C(23) C(18) H(16) 122(2) no . . . C(15) C(19) H(11) 117(2) no . . . C(17) C(19) H(11) 123(2) no . . . C(11) C(20) H(9) 119.4(17) no . . . C(24) C(20) H(9) 120.8(17) no . . . C(13) C(22) H(1) 108.9 no . . . C(13) C(22) H(2) 110.1 no . . . C(13) C(22) H(3) 109.4 no . . . H(1) C(22) H(2) 109.5 no . . . H(1) C(22) H(3) 109.5 no . . . H(2) C(22) H(3) 109.5 no . . . C(18) C(23) H(17) 116(2) no . . . C(21) C(23) H(17) 123(2) no . . . C(17) C(24) H(8) 122(2) no . . . C(20) C(24) H(8) 118(2) no . . . C(14) C(25) H(19) 124(2) no . . . C(21) C(25) H(19) 115(2) no . . . C(21) C(26) H(4) 109.6 no . . . C(21) C(26) H(5) 109.6 no . . . C(21) C(26) H(6) 109.1 no . . . H(4) C(26) H(5) 109.5 no . . . H(4) C(26) H(6) 109.5 no . . . H(5) C(26) H(6) 109.5 no . . . C(16) C(27) H(14) 117(2) no . . . C(16) C(27) H(15) 117.9(18) no . . . H(14) C(27) H(15) 124(3) no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O(4) S(1) N(1) C(8) -24.3(2) ? . . . . O(4) S(1) N(1) C(12) 170.9(2) ? . . . . O(4) S(1) C(10) C(14) -141.5(2) ? . . . . O(4) S(1) C(10) C(18) 37.6(2) ? . . . . O(6) S(1) N(1) C(8) -153.6(2) ? . . . . O(6) S(1) N(1) C(12) 41.6(2) ? . . . . O(6) S(1) C(10) C(14) -5.6(2) ? . . . . O(6) S(1) C(10) C(18) 173.5(2) ? . . . . N(1) S(1) C(10) C(14) 106.6(2) ? . . . . N(1) S(1) C(10) C(18) -74.3(2) ? . . . . C(10) S(1) N(1) C(8) 90.7(2) ? . . . . C(10) S(1) N(1) C(12) -74.1(2) ? . . . . C(8) O(2) C(9) C(11) -121.3(2) ? . . . . C(8) O(2) C(9) C(12) -2.2(2) ? . . . . C(8) O(2) C(9) C(13) 114.2(2) ? . . . . C(9) O(2) C(8) O(1) -175.1(2) ? . . . . C(9) O(2) C(8) N(1) 4.9(2) ? . . . . S(1) N(1) C(8) O(1) 7.7(3) ? . . . . S(1) N(1) C(8) O(2) -172.30(15) ? . . . . S(1) N(1) C(12) O(5) -8.0(3) ? . . . . S(1) N(1) C(12) C(9) 170.94(16) ? . . . . C(8) N(1) C(12) O(5) -174.6(2) ? . . . . C(8) N(1) C(12) C(9) 4.3(2) ? . . . . C(12) N(1) C(8) O(1) 174.1(2) ? . . . . C(12) N(1) C(8) O(2) -5.8(2) ? . . . . O(2) C(9) C(11) C(15) -5.9(3) ? . . . . O(2) C(9) C(11) C(20) 176.3(2) ? . . . . O(2) C(9) C(12) O(5) 177.5(2) ? . . . . O(2) C(9) C(12) N(1) -1.3(2) ? . . . . O(2) C(9) C(13) C(16) -60.3(2) ? . . . . O(2) C(9) C(13) C(22) 63.9(2) ? . . . . C(11) C(9) C(12) O(5) -64.4(3) ? . . . . C(11) C(9) C(12) N(1) 116.8(2) ? . . . . C(12) C(9) C(11) C(15) -119.5(2) ? . . . . C(12) C(9) C(11) C(20) 62.7(2) ? . . . . C(11) C(9) C(13) C(16) 177.0(2) ? . . . . C(11) C(9) C(13) C(22) -58.7(2) ? . . . . C(13) C(9) C(11) C(15) 115.9(2) ? . . . . C(13) C(9) C(11) C(20) -61.9(3) ? . . . . C(12) C(9) C(13) C(16) 51.5(2) ? . . . . C(12) C(9) C(13) C(22) 175.8(2) ? . . . . C(13) C(9) C(12) O(5) 62.1(3) ? . . . . C(13) C(9) C(12) N(1) -116.8(2) ? . . . . S(1) C(10) C(14) C(25) 178.5(2) ? . . . . S(1) C(10) C(18) C(23) -179.8(2) ? . . . . C(14) C(10) C(18) C(23) -0.7(4) ? . . . . C(18) C(10) C(14) C(25) -0.6(4) ? . . . . C(9) C(11) C(15) C(19) -177.2(2) ? . . . . C(9) C(11) C(20) C(24) 177.9(2) ? . . . . C(15) C(11) C(20) C(24) 0.1(3) ? . . . . C(20) C(11) C(15) C(19) 0.6(4) ? . . . . C(9) C(13) C(16) C(27) -108.3(3) ? . . . . C(22) C(13) C(16) C(27) 128.0(3) ? . . . . C(10) C(14) C(25) C(21) 1.2(4) ? . . . . C(11) C(15) C(19) C(17) -0.8(4) ? . . . . C(19) C(17) C(24) C(20) 0.3(5) ? . . . . C(24) C(17) C(19) C(15) 0.4(5) ? . . . . C(10) C(18) C(23) C(21) 1.3(4) ? . . . . C(11) C(20) C(24) C(17) -0.5(5) ? . . . . C(23) C(21) C(25) C(14) -0.7(4) ? . . . . C(25) C(21) C(23) C(18) -0.6(4) ? . . . . C(26) C(21) C(23) C(18) 178.0(3) ? . . . . C(26) C(21) C(25) C(14) -179.3(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S(1) O(1) 3.158(2) ? . . S(1) O(5) 3.109(2) ? . . S(1) C(8) 2.770(2) ? . . S(1) C(12) 2.756(2) ? . . S(1) C(14) 2.708(2) ? . . S(1) C(18) 2.716(3) ? . . O(1) S(1) 3.158(2) ? . . O(1) O(2) 2.224(2) ? . . O(1) O(4) 2.792(3) ? . . O(1) N(1) 2.340(2) ? . . O(1) C(9) 3.456(2) ? . . O(1) C(12) 3.471(3) ? . . O(1) C(13) 3.453(3) ? . 1_545 O(1) C(17) 3.464(4) ? . 4_455 O(1) C(22) 3.340(3) ? . 1_545 O(1) C(24) 3.465(4) ? . 4_455 O(2) O(1) 2.224(2) ? . . O(2) O(5) 3.497(2) ? . . O(2) N(1) 2.232(2) ? . . O(2) C(11) 2.443(2) ? . . O(2) C(12) 2.336(3) ? . . O(2) C(13) 2.444(3) ? . . O(2) C(15) 2.763(3) ? . . O(2) C(16) 2.916(3) ? . . O(2) C(22) 2.953(3) ? . . O(4) O(1) 2.792(3) ? . . O(4) O(5) 3.391(2) ? . 1_545 O(4) O(6) 2.470(3) ? . . O(4) N(1) 2.505(2) ? . . O(4) C(8) 2.950(3) ? . . O(4) C(10) 2.600(3) ? . . O(4) C(18) 3.031(3) ? . . O(4) C(20) 3.431(3) ? . 1_545 O(5) S(1) 3.109(2) ? . . O(5) O(2) 3.497(2) ? . . O(5) O(4) 3.391(2) ? . 1_565 O(5) O(6) 2.892(3) ? . . O(5) N(1) 2.327(2) ? . . O(5) C(8) 3.471(3) ? . . O(5) C(9) 2.440(2) ? . . O(5) C(10) 3.547(3) ? . . O(5) C(11) 3.103(2) ? . . O(5) C(13) 3.074(3) ? . . O(5) C(16) 3.413(4) ? . . O(5) C(20) 3.145(3) ? . . O(5) C(23) 3.419(4) ? . 4_555 O(5) C(26) 3.390(4) ? . 4_555 O(5) C(27) 3.496(4) ? . . O(6) O(4) 2.470(3) ? . . O(6) O(5) 2.892(3) ? . . O(6) N(1) 2.500(3) ? . . O(6) C(10) 2.603(3) ? . . O(6) C(12) 3.018(3) ? . . O(6) C(14) 2.926(3) ? . . O(6) C(14) 3.451(3) ? . 3_656 O(6) C(25) 3.364(4) ? . 3_656 O(6) C(27) 3.566(4) ? . 4_555 N(1) O(1) 2.340(2) ? . . N(1) O(2) 2.232(2) ? . . N(1) O(4) 2.505(2) ? . . N(1) O(5) 2.327(2) ? . . N(1) O(6) 2.500(3) ? . . N(1) C(9) 2.341(2) ? . . N(1) C(10) 2.697(2) ? . . N(1) C(11) 3.413(2) ? . . N(1) C(13) 3.418(3) ? . . N(1) C(16) 3.399(3) ? . . N(1) C(18) 3.319(3) ? . . C(8) S(1) 2.770(2) ? . . C(8) O(4) 2.950(3) ? . . C(8) O(5) 3.471(3) ? . . C(8) C(9) 2.329(3) ? . . C(8) C(10) 3.559(3) ? . . C(8) C(11) 3.411(3) ? . . C(8) C(12) 2.326(3) ? . . C(8) C(13) 3.357(3) ? . . C(8) C(16) 3.364(3) ? . . C(9) O(1) 3.456(2) ? . . C(9) O(5) 2.440(2) ? . . C(9) N(1) 2.341(2) ? . . C(9) C(8) 2.329(3) ? . . C(9) C(15) 2.543(3) ? . . C(9) C(16) 2.518(3) ? . . C(9) C(20) 2.506(3) ? . . C(9) C(22) 2.529(4) ? . . C(9) C(27) 3.473(4) ? . . C(10) O(4) 2.600(3) ? . . C(10) O(5) 3.547(3) ? . . C(10) O(6) 2.603(3) ? . . C(10) N(1) 2.697(2) ? . . C(10) C(8) 3.559(3) ? . . C(10) C(12) 3.380(3) ? . . C(10) C(21) 2.771(3) ? . . C(10) C(23) 2.384(4) ? . . C(10) C(25) 2.386(3) ? . . C(11) O(2) 2.443(2) ? . . C(11) O(5) 3.103(2) ? . . C(11) N(1) 3.413(2) ? . . C(11) C(8) 3.411(3) ? . . C(11) C(12) 2.519(3) ? . . C(11) C(13) 2.562(3) ? . . C(11) C(17) 2.775(3) ? . . C(11) C(19) 2.412(3) ? . . C(11) C(22) 3.020(4) ? . . C(11) C(24) 2.396(4) ? . . C(12) S(1) 2.756(2) ? . . C(12) O(1) 3.471(3) ? . . C(12) O(2) 2.336(3) ? . . C(12) O(6) 3.018(3) ? . . C(12) C(8) 2.326(3) ? . . C(12) C(10) 3.380(3) ? . . C(12) C(11) 2.519(3) ? . . C(12) C(13) 2.518(3) ? . . C(12) C(16) 2.891(4) ? . . C(12) C(20) 3.081(3) ? . . C(12) C(27) 3.373(4) ? . . C(13) O(1) 3.453(3) ? . 1_565 C(13) O(2) 2.444(3) ? . . C(13) O(5) 3.074(3) ? . . C(13) N(1) 3.418(3) ? . . C(13) C(8) 3.357(3) ? . . C(13) C(11) 2.562(3) ? . . C(13) C(12) 2.518(3) ? . . C(13) C(20) 3.120(3) ? . . C(13) C(27) 2.482(4) ? . . C(14) S(1) 2.708(2) ? . . C(14) O(6) 2.926(3) ? . . C(14) O(6) 3.451(3) ? . 3_656 C(14) C(18) 2.412(4) ? . . C(14) C(21) 2.412(4) ? . . C(14) C(23) 2.766(4) ? . . C(15) O(2) 2.763(3) ? . . C(15) C(9) 2.543(3) ? . . C(15) C(17) 2.390(4) ? . . C(15) C(20) 2.395(4) ? . . C(15) C(24) 2.751(4) ? . . C(16) O(2) 2.916(3) ? . . C(16) O(5) 3.413(4) ? . . C(16) N(1) 3.399(3) ? . . C(16) C(8) 3.364(3) ? . . C(16) C(9) 2.518(3) ? . . C(16) C(12) 2.891(4) ? . . C(16) C(22) 2.502(4) ? . . C(17) O(1) 3.464(4) ? . 4_555 C(17) C(11) 2.775(3) ? . . C(17) C(15) 2.390(4) ? . . C(17) C(20) 2.396(3) ? . . C(18) S(1) 2.716(3) ? . . C(18) O(4) 3.031(3) ? . . C(18) N(1) 3.319(3) ? . . C(18) C(14) 2.412(4) ? . . C(18) C(21) 2.409(3) ? . . C(18) C(25) 2.768(4) ? . . C(19) C(11) 2.412(3) ? . . C(19) C(20) 2.761(3) ? . . C(19) C(24) 2.364(4) ? . . C(20) O(4) 3.431(3) ? . 1_565 C(20) O(5) 3.145(3) ? . . C(20) C(9) 2.506(3) ? . . C(20) C(12) 3.081(3) ? . . C(20) C(13) 3.120(3) ? . . C(20) C(15) 2.395(4) ? . . C(20) C(17) 2.396(3) ? . . C(20) C(19) 2.761(3) ? . . C(21) C(10) 2.771(3) ? . . C(21) C(14) 2.412(4) ? . . C(21) C(18) 2.409(3) ? . . C(22) O(1) 3.340(3) ? . 1_565 C(22) O(2) 2.953(3) ? . . C(22) C(9) 2.529(4) ? . . C(22) C(11) 3.020(4) ? . . C(22) C(16) 2.502(4) ? . . C(22) C(22) 3.493(4) ? . 3_667 C(22) C(27) 3.591(4) ? . . C(23) O(5) 3.419(4) ? . 4_455 C(23) C(10) 2.384(4) ? . . C(23) C(14) 2.766(4) ? . . C(23) C(25) 2.381(4) ? . . C(23) C(26) 2.516(4) ? . . C(24) O(1) 3.465(4) ? . 4_555 C(24) C(11) 2.396(4) ? . . C(24) C(15) 2.751(4) ? . . C(24) C(19) 2.364(4) ? . . C(25) O(6) 3.364(4) ? . 3_656 C(25) C(10) 2.386(3) ? . . C(25) C(18) 2.768(4) ? . . C(25) C(23) 2.381(4) ? . . C(25) C(26) 2.507(5) ? . . C(26) O(5) 3.390(4) ? . 4_455 C(26) C(23) 2.516(4) ? . . C(26) C(25) 2.507(5) ? . . C(27) O(5) 3.496(4) ? . . C(27) O(6) 3.566(4) ? . 4_455 C(27) C(9) 3.473(4) ? . . C(27) C(12) 3.373(4) ? . . C(27) C(13) 2.482(4) ? . . C(27) C(22) 3.591(4) ? . . S(1) H(16) 2.82(3) ? . . S(1) H(17) 3.49(3) ? . 4_545 S(1) H(18) 2.82(3) ? . . O(1) H(2) 2.733 ? . 1_545 O(1) H(3) 3.475 ? . 1_545 O(1) H(7) 3.06(4) ? . 4_455 O(1) H(8) 3.06(4) ? . 4_455 O(1) H(9) 3.25(3) ? . 1_545 O(1) H(11) 2.77(3) ? . 2_647 O(1) H(12) 2.82(2) ? . 1_545 O(1) H(16) 2.96(3) ? . . O(2) H(1) 2.910 ? . . O(2) H(3) 2.907 ? . . O(2) H(7) 3.23(3) ? . 2_647 O(2) H(7) 3.49(4) ? . 4_455 O(2) H(10) 2.43(2) ? . . O(2) H(11) 3.19(3) ? . 2_647 O(2) H(12) 3.18(2) ? . . O(2) H(13) 2.80(3) ? . . O(4) H(9) 2.51(2) ? . 1_545 O(4) H(12) 2.74(3) ? . 1_545 O(4) H(15) 3.18(3) ? . 1_545 O(4) H(16) 2.74(3) ? . . O(4) H(17) 2.81(4) ? . 4_545 O(5) H(6) 2.585 ? . 4_555 O(5) H(9) 2.67(2) ? . . O(5) H(12) 2.77(3) ? . . O(5) H(14) 3.06(5) ? . 4_555 O(5) H(15) 3.08(3) ? . . O(5) H(17) 3.00(4) ? . 4_555 O(5) H(18) 3.31(3) ? . . O(6) H(5) 3.426 ? . 4_555 O(6) H(6) 3.526 ? . 4_555 O(6) H(14) 2.99(4) ? . 4_555 O(6) H(17) 3.29(3) ? . 4_545 O(6) H(18) 2.55(3) ? . . O(6) H(18) 3.15(3) ? . 3_656 O(6) H(19) 2.99(4) ? . 3_656 N(1) H(13) 3.47(3) ? . . N(1) H(16) 3.21(3) ? . . C(8) H(7) 3.59(4) ? . 4_455 C(8) H(10) 3.36(2) ? . . C(8) H(11) 3.27(3) ? . 2_647 C(8) H(13) 3.14(3) ? . . C(8) H(16) 3.19(3) ? . . C(9) H(1) 2.935 ? . . C(9) H(2) 3.298 ? . . C(9) H(3) 2.516 ? . . C(9) H(9) 2.64(2) ? . . C(9) H(10) 2.71(2) ? . . C(9) H(12) 1.96(2) ? . . C(9) H(13) 2.86(3) ? . . C(9) H(15) 3.57(3) ? . . C(10) H(5) 3.132 ? . 2_546 C(10) H(16) 2.07(3) ? . . C(10) H(17) 3.17(4) ? . . C(10) H(18) 2.06(3) ? . . C(10) H(19) 3.24(3) ? . . C(11) H(3) 2.538 ? . . C(11) H(8) 3.22(3) ? . . C(11) H(9) 2.03(2) ? . . C(11) H(10) 2.01(2) ? . . C(11) H(11) 3.22(3) ? . . C(11) H(12) 2.65(2) ? . . C(11) H(13) 3.30(3) ? . 4_555 C(12) H(9) 2.91(2) ? . . C(12) H(12) 2.60(3) ? . . C(12) H(13) 3.30(3) ? . . C(12) H(14) 3.33(5) ? . 4_555 C(12) H(15) 3.29(3) ? . . C(13) H(1) 2.046 ? . . C(13) H(2) 2.059 ? . . C(13) H(3) 2.052 ? . . C(13) H(9) 2.97(3) ? . . C(13) H(13) 2.08(3) ? . . C(13) H(14) 3.31(4) ? . . C(13) H(15) 2.66(3) ? . . C(14) H(4) 3.394 ? . 2_556 C(14) H(5) 3.151 ? . 2_546 C(14) H(16) 3.30(3) ? . . C(14) H(18) 3.39(4) ? . 3_656 C(14) H(19) 2.05(3) ? . . C(15) H(1) 3.376 ? . 4_555 C(15) H(3) 2.887 ? . . C(15) H(7) 3.27(3) ? . . C(15) H(9) 3.26(2) ? . . C(15) H(11) 1.98(3) ? . . C(15) H(13) 3.34(3) ? . 4_555 C(16) H(1) 2.520 ? . . C(16) H(2) 2.893 ? . . C(16) H(3) 3.272 ? . . C(16) H(12) 2.01(3) ? . . C(16) H(14) 1.92(4) ? . . C(16) H(15) 2.00(3) ? . . C(17) H(1) 3.551 ? . 4_555 C(17) H(2) 3.433 ? . 4_565 C(17) H(7) 3.34(3) ? . 3_767 C(17) H(8) 2.02(3) ? . . C(17) H(9) 3.26(2) ? . . C(17) H(10) 3.20(3) ? . . C(17) H(10) 3.03(3) ? . 2_657 C(17) H(11) 2.01(3) ? . . C(17) H(13) 3.26(3) ? . 4_555 C(18) H(5) 3.403 ? . 2_546 C(18) H(14) 3.44(4) ? . . C(18) H(15) 3.45(3) ? . 1_545 C(18) H(17) 1.94(4) ? . . C(18) H(18) 3.29(3) ? . . C(18) H(19) 3.47(3) ? . 2_546 C(19) H(1) 2.986 ? . 4_555 C(19) H(7) 2.03(3) ? . . C(19) H(7) 3.39(3) ? . 3_767 C(19) H(8) 3.21(3) ? . . C(19) H(10) 2.00(3) ? . . C(19) H(10) 3.13(3) ? . 2_657 C(19) H(13) 3.33(3) ? . 4_555 C(20) H(3) 3.234 ? . . C(20) H(7) 3.24(3) ? . . C(20) H(8) 1.99(3) ? . . C(20) H(10) 3.22(3) ? . . C(20) H(12) 2.75(3) ? . . C(20) H(13) 3.23(3) ? . 4_555 C(20) H(17) 3.45(3) ? . 4_555 C(21) H(4) 2.035 ? . . C(21) H(5) 2.035 ? . . C(21) H(6) 2.028 ? . . C(21) H(14) 3.26(4) ? . . C(21) H(16) 3.31(3) ? . . C(21) H(17) 2.02(3) ? . . C(21) H(18) 3.29(4) ? . . C(21) H(19) 1.95(4) ? . . C(21) H(19) 3.03(3) ? . 2_546 C(22) H(1) 3.232 ? . 3_667 C(22) H(2) 3.434 ? . 3_667 C(22) H(3) 3.239 ? . 3_667 C(22) H(8) 3.53(3) ? . 4_465 C(22) H(11) 3.58(3) ? . 2_657 C(22) H(12) 2.11(3) ? . . C(22) H(13) 2.72(3) ? . . C(23) H(4) 2.944 ? . . C(23) H(5) 3.238 ? . . C(23) H(6) 2.598 ? . . C(23) H(9) 3.42(3) ? . 4_455 C(23) H(14) 3.21(4) ? . . C(23) H(16) 2.08(3) ? . . C(23) H(19) 3.18(4) ? . . C(23) H(19) 2.93(3) ? . 2_546 C(24) H(2) 3.327 ? . 4_565 C(24) H(7) 2.01(3) ? . . C(24) H(9) 2.05(2) ? . . C(24) H(10) 3.55(3) ? . 2_657 C(24) H(11) 3.21(3) ? . . C(24) H(13) 3.20(3) ? . 4_555 C(24) H(16) 3.34(3) ? . 4_555 C(25) H(4) 2.920 ? . . C(25) H(4) 3.274 ? . 2_556 C(25) H(5) 2.606 ? . . C(25) H(5) 3.414 ? . 2_546 C(25) H(6) 3.232 ? . . C(25) H(14) 3.52(4) ? . . C(25) H(17) 3.21(4) ? . . C(25) H(18) 2.06(3) ? . . C(26) H(4) 3.314 ? . 3_556 C(26) H(6) 3.370 ? . 3_556 C(26) H(17) 2.70(3) ? . . C(26) H(18) 3.37(3) ? . 4_455 C(26) H(19) 2.57(4) ? . . C(26) H(19) 3.41(4) ? . 2_546 C(27) H(12) 2.54(2) ? . . C(27) H(13) 1.89(3) ? . . C(27) H(16) 3.51(3) ? . 1_565 H(1) O(2) 2.910 ? . . H(1) C(9) 2.935 ? . . H(1) C(13) 2.046 ? . . H(1) C(15) 3.376 ? . 4_455 H(1) C(16) 2.520 ? . . H(1) C(17) 3.551 ? . 4_455 H(1) C(19) 2.986 ? . 4_455 H(1) C(22) 3.232 ? . 3_667 H(1) H(1) 3.241 ? . 3_667 H(1) H(2) 1.551 ? . . H(1) H(2) 3.072 ? . 3_667 H(1) H(3) 1.551 ? . . H(1) H(3) 2.853 ? . 3_667 H(1) H(7) 3.341 ? . 2_647 H(1) H(10) 3.457 ? . 4_455 H(1) H(11) 2.870 ? . 4_455 H(1) H(12) 2.822 ? . . H(1) H(13) 2.421 ? . . H(2) O(1) 2.733 ? . 1_565 H(2) C(9) 3.298 ? . . H(2) C(13) 2.059 ? . . H(2) C(16) 2.893 ? . . H(2) C(17) 3.433 ? . 4_465 H(2) C(22) 3.434 ? . 3_667 H(2) C(24) 3.327 ? . 4_465 H(2) H(1) 1.551 ? . . H(2) H(1) 3.072 ? . 3_667 H(2) H(3) 1.551 ? . . H(2) H(3) 3.080 ? . 3_667 H(2) H(7) 2.825 ? . 4_465 H(2) H(8) 2.683 ? . 4_465 H(2) H(11) 3.144 ? . 2_657 H(2) H(12) 2.317 ? . . H(2) H(13) 3.222 ? . . H(3) O(1) 3.475 ? . 1_565 H(3) O(2) 2.907 ? . . H(3) C(9) 2.516 ? . . H(3) C(11) 2.538 ? . . H(3) C(13) 2.052 ? . . H(3) C(15) 2.887 ? . . H(3) C(16) 3.272 ? . . H(3) C(20) 3.234 ? . . H(3) C(22) 3.239 ? . 3_667 H(3) H(1) 1.551 ? . . H(3) H(1) 2.853 ? . 3_667 H(3) H(2) 1.551 ? . . H(3) H(2) 3.080 ? . 3_667 H(3) H(3) 3.255 ? . 3_667 H(3) H(7) 3.478 ? . 2_647 H(3) H(9) 3.568 ? . . H(3) H(10) 3.049 ? . . H(3) H(11) 3.124 ? . 2_657 H(3) H(12) 2.529 ? . . H(3) H(13) 3.477 ? . . H(4) C(14) 3.394 ? . 2_546 H(4) C(21) 2.035 ? . . H(4) C(23) 2.944 ? . . H(4) C(25) 2.920 ? . . H(4) C(25) 3.274 ? . 2_546 H(4) C(26) 3.314 ? . 3_556 H(4) H(4) 3.107 ? . 3_556 H(4) H(5) 1.551 ? . . H(4) H(6) 1.551 ? . . H(4) H(6) 2.761 ? . 3_556 H(4) H(15) 3.210 ? . 2_546 H(4) H(17) 3.062 ? . . H(4) H(18) 3.039 ? . 2_546 H(4) H(19) 2.905 ? . . H(4) H(19) 2.908 ? . 2_546 H(5) O(6) 3.426 ? . 4_455 H(5) C(10) 3.132 ? . 2_556 H(5) C(14) 3.151 ? . 2_556 H(5) C(18) 3.403 ? . 2_556 H(5) C(21) 2.035 ? . . H(5) C(23) 3.238 ? . . H(5) C(25) 2.606 ? . . H(5) C(25) 3.414 ? . 2_556 H(5) H(4) 1.551 ? . . H(5) H(6) 1.551 ? . . H(5) H(17) 3.520 ? . . H(5) H(18) 3.553 ? . 2_556 H(5) H(18) 2.994 ? . 4_455 H(5) H(19) 2.373 ? . . H(6) O(5) 2.585 ? . 4_455 H(6) O(6) 3.526 ? . 4_455 H(6) C(21) 2.028 ? . . H(6) C(23) 2.598 ? . . H(6) C(25) 3.232 ? . . H(6) C(26) 3.370 ? . 3_556 H(6) H(4) 1.551 ? . . H(6) H(4) 2.761 ? . 3_556 H(6) H(5) 1.551 ? . . H(6) H(6) 3.226 ? . 3_556 H(6) H(17) 2.486 ? . . H(6) H(18) 2.892 ? . 4_455 H(6) H(19) 3.408 ? . . H(7) O(1) 3.06(4) ? . 4_555 H(7) O(2) 3.23(3) ? . 2_657 H(7) O(2) 3.49(4) ? . 4_555 H(7) C(8) 3.59(4) ? . 4_555 H(7) C(15) 3.27(3) ? . . H(7) C(17) 3.34(3) ? . 3_767 H(7) C(19) 2.03(3) ? . . H(7) C(19) 3.39(3) ? . 3_767 H(7) C(20) 3.24(3) ? . . H(7) C(24) 2.01(3) ? . . H(7) H(1) 3.341 ? . 2_657 H(7) H(2) 2.825 ? . 4_565 H(7) H(3) 3.478 ? . 2_657 H(7) H(7) 2.77(4) ? . 3_767 H(7) H(8) 2.31(4) ? . . H(7) H(10) 3.11(5) ? . 2_657 H(7) H(11) 2.37(5) ? . . H(7) H(11) 2.91(5) ? . 3_767 H(8) O(1) 3.06(4) ? . 4_555 H(8) C(11) 3.22(3) ? . . H(8) C(17) 2.02(3) ? . . H(8) C(19) 3.21(3) ? . . H(8) C(20) 1.99(3) ? . . H(8) C(22) 3.53(3) ? . 4_565 H(8) H(2) 2.683 ? . 4_565 H(8) H(7) 2.31(4) ? . . H(8) H(9) 2.30(4) ? . . H(8) H(16) 2.77(5) ? . 4_555 H(9) O(1) 3.25(3) ? . 1_565 H(9) O(4) 2.51(2) ? . 1_565 H(9) O(5) 2.67(2) ? . . H(9) C(9) 2.64(2) ? . . H(9) C(11) 2.03(2) ? . . H(9) C(12) 2.91(2) ? . . H(9) C(13) 2.97(3) ? . . H(9) C(15) 3.26(2) ? . . H(9) C(17) 3.26(2) ? . . H(9) C(23) 3.42(3) ? . 4_555 H(9) C(24) 2.05(2) ? . . H(9) H(3) 3.568 ? . . H(9) H(8) 2.30(4) ? . . H(9) H(12) 2.36(4) ? . . H(9) H(16) 3.46(5) ? . 4_555 H(9) H(17) 2.74(5) ? . 4_555 H(10) O(2) 2.43(2) ? . . H(10) C(8) 3.36(2) ? . . H(10) C(9) 2.71(2) ? . . H(10) C(11) 2.01(2) ? . . H(10) C(17) 3.20(3) ? . . H(10) C(17) 3.03(3) ? . 2_647 H(10) C(19) 2.00(3) ? . . H(10) C(19) 3.13(3) ? . 2_647 H(10) C(20) 3.22(3) ? . . H(10) C(24) 3.55(3) ? . 2_647 H(10) H(1) 3.457 ? . 4_555 H(10) H(3) 3.049 ? . . H(10) H(7) 3.11(5) ? . 2_647 H(10) H(11) 2.25(4) ? . . H(10) H(11) 3.29(4) ? . 2_647 H(11) O(1) 2.77(3) ? . 2_657 H(11) O(2) 3.19(3) ? . 2_657 H(11) C(8) 3.27(3) ? . 2_657 H(11) C(11) 3.22(3) ? . . H(11) C(15) 1.98(3) ? . . H(11) C(17) 2.01(3) ? . . H(11) C(22) 3.58(3) ? . 2_647 H(11) C(24) 3.21(3) ? . . H(11) H(1) 2.870 ? . 4_555 H(11) H(2) 3.144 ? . 2_647 H(11) H(3) 3.124 ? . 2_647 H(11) H(7) 2.37(5) ? . . H(11) H(7) 2.91(5) ? . 3_767 H(11) H(10) 2.25(4) ? . . H(11) H(10) 3.29(4) ? . 2_657 H(12) O(1) 2.82(2) ? . 1_565 H(12) O(2) 3.18(2) ? . . H(12) O(4) 2.74(3) ? . 1_565 H(12) O(5) 2.77(3) ? . . H(12) C(9) 1.96(2) ? . . H(12) C(11) 2.65(2) ? . . H(12) C(12) 2.60(3) ? . . H(12) C(16) 2.01(3) ? . . H(12) C(20) 2.75(3) ? . . H(12) C(22) 2.11(3) ? . . H(12) C(27) 2.54(2) ? . . H(12) H(1) 2.822 ? . . H(12) H(2) 2.317 ? . . H(12) H(3) 2.529 ? . . H(12) H(9) 2.36(4) ? . . H(12) H(13) 2.79(4) ? . . H(12) H(14) 3.46(5) ? . . H(12) H(15) 2.34(4) ? . . H(12) H(16) 3.42(4) ? . 1_565 H(13) O(2) 2.80(3) ? . . H(13) N(1) 3.47(3) ? . . H(13) C(8) 3.14(3) ? . . H(13) C(9) 2.86(3) ? . . H(13) C(11) 3.30(3) ? . 4_455 H(13) C(12) 3.30(3) ? . . H(13) C(13) 2.08(3) ? . . H(13) C(15) 3.34(3) ? . 4_455 H(13) C(17) 3.26(3) ? . 4_455 H(13) C(19) 3.33(3) ? . 4_455 H(13) C(20) 3.23(3) ? . 4_455 H(13) C(22) 2.72(3) ? . . H(13) C(24) 3.20(3) ? . 4_455 H(13) C(27) 1.89(3) ? . . H(13) H(1) 2.421 ? . . H(13) H(2) 3.222 ? . . H(13) H(3) 3.477 ? . . H(13) H(12) 2.79(4) ? . . H(13) H(14) 2.14(5) ? . . H(13) H(15) 2.77(5) ? . . H(14) O(5) 3.06(5) ? . 4_455 H(14) O(6) 2.99(4) ? . 4_455 H(14) C(12) 3.33(5) ? . 4_455 H(14) C(13) 3.31(4) ? . . H(14) C(16) 1.92(4) ? . . H(14) C(18) 3.44(4) ? . . H(14) C(21) 3.26(4) ? . . H(14) C(23) 3.21(4) ? . . H(14) C(25) 3.52(4) ? . . H(14) H(12) 3.46(5) ? . . H(14) H(13) 2.14(5) ? . . H(14) H(15) 1.73(6) ? . . H(14) H(17) 3.53(5) ? . . H(15) O(4) 3.18(3) ? . 1_565 H(15) O(5) 3.08(3) ? . . H(15) C(9) 3.57(3) ? . . H(15) C(12) 3.29(3) ? . . H(15) C(13) 2.66(3) ? . . H(15) C(16) 2.00(3) ? . . H(15) C(18) 3.45(3) ? . 1_565 H(15) H(4) 3.210 ? . 2_556 H(15) H(12) 2.34(4) ? . . H(15) H(13) 2.77(5) ? . . H(15) H(14) 1.73(6) ? . . H(15) H(16) 2.89(5) ? . 1_565 H(16) S(1) 2.82(3) ? . . H(16) O(1) 2.96(3) ? . . H(16) O(4) 2.74(3) ? . . H(16) N(1) 3.21(3) ? . . H(16) C(8) 3.19(3) ? . . H(16) C(10) 2.07(3) ? . . H(16) C(14) 3.30(3) ? . . H(16) C(21) 3.31(3) ? . . H(16) C(23) 2.08(3) ? . . H(16) C(24) 3.34(3) ? . 4_455 H(16) C(27) 3.51(3) ? . 1_545 H(16) H(8) 2.77(5) ? . 4_455 H(16) H(9) 3.46(5) ? . 4_455 H(16) H(12) 3.42(4) ? . 1_545 H(16) H(15) 2.89(5) ? . 1_545 H(16) H(17) 2.29(4) ? . . H(17) S(1) 3.49(3) ? . 4_445 H(17) O(4) 2.81(4) ? . 4_445 H(17) O(5) 3.00(3) ? . 4_455 H(17) O(6) 3.29(3) ? . 4_445 H(17) C(10) 3.17(4) ? . . H(17) C(18) 1.94(4) ? . . H(17) C(20) 3.45(3) ? . 4_455 H(17) C(21) 2.02(3) ? . . H(17) C(25) 3.21(4) ? . . H(17) C(26) 2.70(3) ? . . H(17) H(4) 3.062 ? . . H(17) H(5) 3.520 ? . . H(17) H(6) 2.486 ? . . H(17) H(9) 2.74(5) ? . 4_455 H(17) H(14) 3.53(5) ? . . H(17) H(16) 2.29(4) ? . . H(17) H(19) 3.03(5) ? . 2_546 H(18) S(1) 2.82(3) ? . . H(18) O(5) 3.31(3) ? . . H(18) O(6) 2.55(3) ? . . H(18) O(6) 3.15(3) ? . 3_656 H(18) C(10) 2.06(3) ? . . H(18) C(14) 3.39(4) ? . 3_656 H(18) C(18) 3.29(3) ? . . H(18) C(21) 3.29(4) ? . . H(18) C(25) 2.06(3) ? . . H(18) C(26) 3.37(3) ? . 4_555 H(18) H(4) 3.039 ? . 2_556 H(18) H(5) 3.553 ? . 2_546 H(18) H(5) 2.994 ? . 4_555 H(18) H(6) 2.892 ? . 4_555 H(18) H(18) 2.90(5) ? . 3_656 H(18) H(19) 2.40(5) ? . . H(19) O(6) 2.99(4) ? . 3_656 H(19) C(10) 3.24(3) ? . . H(19) C(14) 2.05(3) ? . . H(19) C(18) 3.47(3) ? . 2_556 H(19) C(21) 1.95(4) ? . . H(19) C(21) 3.03(3) ? . 2_556 H(19) C(23) 3.18(4) ? . . H(19) C(23) 2.93(3) ? . 2_556 H(19) C(26) 2.57(4) ? . . H(19) C(26) 3.41(4) ? . 2_556 H(19) H(4) 2.905 ? . . H(19) H(4) 2.908 ? . 2_556 H(19) H(5) 2.373 ? . . H(19) H(6) 3.408 ? . . H(19) H(17) 3.03(5) ? . 2_556 H(19) H(18) 2.40(5) ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment 'CIF_9.cif' #------------------------------------------------------------------------------ data_n654-061021 _database_code_depnum_ccdc_archive 'CCDC 729638' #TrackingRef 'CIF_9.cif' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C25 H22 I N O3 ' _chemical_formula_moiety 'C25 H22 I N O3 ' _chemical_formula_weight 511.36 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 6.6009(1) _cell_length_b 25.4575(3) _cell_length_c 13.4714(2) _cell_angle_alpha 90 _cell_angle_beta 95.8569(4) _cell_angle_gamma 90 _cell_volume 2251.94(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 33037 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 30.5 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 1.448 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.557 _exptl_absorpt_correction_T_max 0.749 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 26912 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_theta_max 30.50 _diffrn_measured_fraction_theta_max 0.9988 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.9988 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 4.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 4.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6876 _reflns_number_gt 3717 _reflns_threshold_expression F^2^>4.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1224 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3717 _refine_ls_number_parameters 359 _refine_ls_goodness_of_fit_ref 1.941 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0061 _refine_diff_density_max 1.07 _refine_diff_density_min -0.30 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; I I -0.474 1.812 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I(1) I 0.22887(6) 0.04296(1) 0.06947(3) 0.0884(1) Uani 1.00 d . . . O(1) O 0.7173(3) 0.34389(8) 0.1908(2) 0.0365(6) Uani 1.00 d . . . O(2) O 0.8600(3) 0.26912(9) 0.1461(2) 0.0444(6) Uani 1.00 d . . . O(3) O 0.2248(3) 0.30731(9) 0.2334(2) 0.0375(6) Uani 1.00 d . . . N(1) N 0.5140(3) 0.27521(9) 0.1572(2) 0.0326(6) Uani 1.00 d . . . C(1) C 0.7099(4) 0.2924(1) 0.1642(2) 0.0333(7) Uani 1.00 d . . . C(2) C 0.3715(4) 0.3198(1) 0.1704(2) 0.0300(7) Uani 1.00 d . . . C(3) C 0.5265(4) 0.3584(1) 0.2298(2) 0.0317(7) Uani 1.00 d . . . C(4) C 0.4552(4) 0.2228(1) 0.1367(2) 0.0316(7) Uani 1.00 d . . . C(5) C 0.5850(5) 0.1810(1) 0.1622(3) 0.0398(8) Uani 1.00 d . . . C(6) C 0.5228(6) 0.1300(1) 0.1427(3) 0.0464(9) Uani 1.00 d . . . C(7) C 0.3272(6) 0.1200(1) 0.0996(3) 0.0466(9) Uani 1.00 d . . . C(8) C 0.1950(5) 0.1607(1) 0.0744(3) 0.0470(10) Uani 1.00 d . . . C(9) C 0.2596(5) 0.2124(1) 0.0909(3) 0.0407(9) Uani 1.00 d . . . C(10) C 0.2833(4) 0.3403(1) 0.0682(2) 0.0339(8) Uani 1.00 d . . . C(11) C 0.3803(6) 0.3323(2) -0.0162(3) 0.049(1) Uani 1.00 d . . . C(12) C 0.2961(9) 0.3507(2) -0.1080(4) 0.070(2) Uani 1.00 d . . . C(13) C 0.1149(9) 0.3778(2) -0.1158(4) 0.076(2) Uani 1.00 d . . . C(14) C 0.0214(7) 0.3871(2) -0.0320(4) 0.068(1) Uani 1.00 d . . . C(15) C 0.1029(5) 0.3683(2) 0.0601(3) 0.049(1) Uani 1.00 d . . . C(16) C 0.4815(5) 0.4157(1) 0.2062(3) 0.0401(8) Uani 1.00 d . . . C(17) C 0.6035(7) 0.4454(1) 0.1504(3) 0.053(1) Uani 1.00 d . . . C(18) C 0.5575(9) 0.4982(2) 0.1310(4) 0.072(1) Uani 1.00 d . . . C(19) C 0.3937(10) 0.5208(2) 0.1667(4) 0.081(2) Uani 1.00 d . . . C(20) C 0.2718(8) 0.4919(2) 0.2229(5) 0.079(2) Uani 1.00 d . . . C(21) C 0.3158(7) 0.4395(2) 0.2430(4) 0.061(1) Uani 1.00 d . . . C(22) C 0.5568(5) 0.3485(1) 0.3439(3) 0.0432(9) Uani 1.00 d . . . C(23) C 0.6026(6) 0.2920(2) 0.3709(3) 0.052(1) Uani 1.00 d . . . C(24) C 0.7863(8) 0.2718(2) 0.3946(4) 0.067(1) Uani 1.00 d . . . C(25) C 0.7190(8) 0.3859(2) 0.3936(4) 0.061(1) Uani 1.00 d . . . H(1) H 0.149(7) 0.297(2) 0.200(3) 0.05(1) Uiso 1.00 calc . . . H(2) H 0.710(6) 0.187(1) 0.191(3) 0.039(9) Uiso 1.00 calc . . . H(3) H 0.614(8) 0.103(2) 0.170(4) 0.08(1) Uiso 1.00 calc . . . H(4) H 0.063(7) 0.157(2) 0.046(3) 0.05(1) Uiso 1.00 calc . . . H(5) H 0.167(7) 0.244(2) 0.067(3) 0.06(1) Uiso 1.00 calc . . . H(6) H 0.496(7) 0.315(2) -0.010(3) 0.05(1) Uiso 1.00 calc . . . H(7) H 0.366(8) 0.346(2) -0.157(4) 0.08(2) Uiso 1.00 calc . . . H(8) H 0.056(8) 0.390(2) -0.179(4) 0.09(1) Uiso 1.00 calc . . . H(9) H -0.098(7) 0.404(2) -0.033(4) 0.07(1) Uiso 1.00 calc . . . H(10) H 0.029(6) 0.377(2) 0.116(3) 0.05(1) Uiso 1.00 calc . . . H(11) H 0.712(6) 0.430(2) 0.125(3) 0.05(1) Uiso 1.00 calc . . . H(12) H 0.674(9) 0.521(3) 0.097(5) 0.11(2) Uiso 1.00 calc . . . H(13) H 0.359(10) 0.554(2) 0.148(5) 0.11(2) Uiso 1.00 calc . . . H(14) H 0.162(8) 0.502(2) 0.246(4) 0.09(2) Uiso 1.00 calc . . . H(15) H 0.245(6) 0.421(2) 0.287(3) 0.05(1) Uiso 1.00 calc . . . H(16) H 0.417(7) 0.357(2) 0.367(3) 0.05(1) Uiso 1.00 calc . . . H(17) H 0.479(9) 0.272(2) 0.367(4) 0.09(2) Uiso 1.00 calc . . . H(18) H 0.788(9) 0.231(3) 0.403(5) 0.11(2) Uiso 1.00 calc . . . H(19) H 0.907(8) 0.294(2) 0.388(4) 0.08(1) Uiso 1.00 calc . . . H(20) H 0.754(6) 0.378(2) 0.460(3) 0.05(1) Uiso 1.00 calc . . . H(21) H 0.835(7) 0.384(2) 0.366(3) 0.06(1) Uiso 1.00 calc . . . H(22) H 0.683(7) 0.418(2) 0.380(4) 0.07(1) Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.1093(3) 0.0350(2) 0.1137(4) -0.0172(1) -0.0232(2) -0.0043(1) O(1) 0.0255(9) 0.033(1) 0.052(1) -0.0044(8) 0.0070(9) -0.0049(9) O(2) 0.0181(9) 0.043(1) 0.072(2) -0.0005(9) 0.0052(10) -0.008(1) O(3) 0.025(1) 0.045(1) 0.043(1) -0.0064(9) 0.0041(10) 0.0027(10) N(1) 0.024(1) 0.030(1) 0.044(2) -0.0008(9) 0.0027(10) -0.0033(10) C(1) 0.021(1) 0.034(1) 0.045(2) -0.004(1) 0.003(1) -0.002(1) C(2) 0.020(1) 0.032(1) 0.038(2) -0.001(1) 0.004(1) 0.000(1) C(3) 0.021(1) 0.031(1) 0.043(2) -0.001(1) 0.001(1) -0.005(1) C(4) 0.030(1) 0.031(1) 0.034(2) -0.003(1) 0.004(1) -0.002(1) C(5) 0.029(1) 0.037(1) 0.052(2) 0.000(1) -0.004(1) 0.003(1) C(6) 0.050(2) 0.032(1) 0.057(2) 0.003(1) 0.000(2) 0.005(1) C(7) 0.057(2) 0.032(1) 0.049(2) -0.009(1) -0.002(2) -0.002(1) C(8) 0.037(2) 0.042(2) 0.059(2) -0.007(1) -0.008(2) -0.003(1) C(9) 0.030(1) 0.036(2) 0.055(2) -0.003(1) -0.004(1) -0.005(1) C(10) 0.029(1) 0.034(1) 0.039(2) -0.005(1) 0.001(1) -0.002(1) C(11) 0.049(2) 0.054(2) 0.045(2) 0.010(2) 0.009(2) 0.001(2) C(12) 0.096(4) 0.074(3) 0.043(3) 0.011(3) 0.018(2) 0.002(2) C(13) 0.093(4) 0.084(3) 0.049(3) 0.010(3) -0.008(3) 0.023(2) C(14) 0.049(2) 0.085(3) 0.069(3) 0.025(2) -0.006(2) 0.022(2) C(15) 0.032(2) 0.060(2) 0.055(2) 0.009(2) 0.001(2) 0.011(2) C(16) 0.039(2) 0.033(1) 0.046(2) 0.000(1) -0.004(1) -0.005(1) C(17) 0.065(2) 0.039(2) 0.056(2) -0.002(2) 0.007(2) 0.002(2) C(18) 0.104(4) 0.040(2) 0.070(3) -0.002(2) -0.001(3) 0.005(2) C(19) 0.110(4) 0.039(2) 0.086(4) 0.011(3) -0.030(3) 0.003(2) C(20) 0.069(3) 0.058(3) 0.106(4) 0.028(3) -0.008(3) -0.020(3) C(21) 0.054(2) 0.051(2) 0.079(3) 0.017(2) 0.009(2) -0.006(2) C(22) 0.044(2) 0.045(2) 0.040(2) -0.002(1) -0.001(1) -0.004(1) C(23) 0.060(2) 0.050(2) 0.043(2) -0.004(2) -0.002(2) 0.005(2) C(24) 0.076(3) 0.056(2) 0.064(3) 0.008(2) -0.014(2) 0.009(2) C(25) 0.066(3) 0.056(2) 0.057(3) -0.016(2) -0.016(2) -0.006(2) #------------------------------------------------------------------------------ _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution 'DIRDIF94 (PATTY)' _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I(1) C(7) 2.092(3) . . yes O(1) C(1) 1.358(4) . . yes O(1) C(3) 1.460(3) . . yes O(2) C(1) 1.201(4) . . yes O(3) C(2) 1.387(4) . . yes N(1) C(1) 1.359(4) . . yes N(1) C(2) 1.496(4) . . yes N(1) C(4) 1.408(4) . . yes C(2) C(3) 1.577(4) . . yes C(2) C(10) 1.532(4) . . yes C(3) C(16) 1.518(4) . . yes C(3) C(22) 1.550(5) . . yes C(4) C(5) 1.387(4) . . yes C(4) C(9) 1.399(4) . . yes C(5) C(6) 1.379(5) . . yes C(6) C(7) 1.384(5) . . yes C(7) C(8) 1.375(5) . . yes C(8) C(9) 1.394(5) . . yes C(10) C(11) 1.376(5) . . yes C(10) C(15) 1.383(5) . . yes C(11) C(12) 1.385(6) . . yes C(12) C(13) 1.376(8) . . yes C(13) C(14) 1.361(7) . . yes C(14) C(15) 1.385(6) . . yes C(16) C(17) 1.381(6) . . yes C(16) C(21) 1.385(5) . . yes C(17) C(18) 1.398(6) . . yes C(18) C(19) 1.355(8) . . yes C(19) C(20) 1.372(8) . . yes C(20) C(21) 1.386(7) . . yes C(22) C(23) 1.507(5) . . yes C(22) C(25) 1.534(5) . . yes C(23) C(24) 1.326(6) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) O(1) C(3) 109.2(2) . . . yes C(1) N(1) C(2) 110.7(2) . . . yes C(1) N(1) C(4) 124.1(2) . . . yes C(2) N(1) C(4) 125.2(2) . . . yes O(1) C(1) O(2) 121.5(2) . . . yes O(1) C(1) N(1) 109.7(2) . . . yes O(2) C(1) N(1) 128.7(3) . . . yes O(3) C(2) N(1) 112.7(2) . . . yes O(3) C(2) C(3) 106.9(2) . . . yes O(3) C(2) C(10) 113.7(2) . . . yes N(1) C(2) C(3) 98.6(2) . . . yes N(1) C(2) C(10) 109.7(2) . . . yes C(3) C(2) C(10) 114.2(2) . . . yes O(1) C(3) C(2) 101.5(2) . . . yes O(1) C(3) C(16) 109.0(2) . . . yes O(1) C(3) C(22) 106.7(2) . . . yes C(2) C(3) C(16) 113.0(2) . . . yes C(2) C(3) C(22) 114.4(2) . . . yes C(16) C(3) C(22) 111.5(3) . . . yes N(1) C(4) C(5) 121.8(3) . . . yes N(1) C(4) C(9) 119.4(3) . . . yes C(5) C(4) C(9) 118.8(3) . . . yes C(4) C(5) C(6) 120.7(3) . . . yes C(5) C(6) C(7) 120.1(3) . . . yes I(1) C(7) C(6) 120.8(3) . . . yes I(1) C(7) C(8) 118.8(3) . . . yes C(6) C(7) C(8) 120.3(3) . . . yes C(7) C(8) C(9) 119.8(3) . . . yes C(4) C(9) C(8) 120.2(3) . . . yes C(2) C(10) C(11) 121.8(3) . . . yes C(2) C(10) C(15) 119.5(3) . . . yes C(11) C(10) C(15) 118.7(3) . . . yes C(10) C(11) C(12) 120.7(4) . . . yes C(11) C(12) C(13) 120.2(4) . . . yes C(12) C(13) C(14) 119.2(4) . . . yes C(13) C(14) C(15) 121.0(4) . . . yes C(10) C(15) C(14) 120.1(4) . . . yes C(3) C(16) C(17) 121.8(3) . . . yes C(3) C(16) C(21) 119.4(3) . . . yes C(17) C(16) C(21) 118.7(4) . . . yes C(16) C(17) C(18) 120.0(4) . . . yes C(17) C(18) C(19) 120.5(5) . . . yes C(18) C(19) C(20) 120.2(4) . . . yes C(19) C(20) C(21) 120.0(5) . . . yes C(16) C(21) C(20) 120.6(5) . . . yes C(3) C(22) C(23) 113.3(3) . . . yes C(3) C(22) C(25) 110.2(3) . . . yes C(23) C(22) C(25) 111.9(3) . . . yes C(22) C(23) C(24) 125.7(4) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I(1) C(7) C(6) C(5) -179.9(3) . . . . yes I(1) C(7) C(8) C(9) -178.0(3) . . . . yes O(1) C(1) N(1) C(2) 6.0(4) . . . . yes O(1) C(1) N(1) C(4) -176.2(3) . . . . yes O(1) C(3) C(2) O(3) 146.9(2) . . . . yes O(1) C(3) C(2) N(1) 29.9(3) . . . . yes O(1) C(3) C(2) C(10) -86.4(3) . . . . yes O(1) C(3) C(16) C(17) 3.9(4) . . . . yes O(1) C(3) C(16) C(21) -174.9(3) . . . . yes O(1) C(3) C(22) C(23) -61.0(3) . . . . yes O(1) C(3) C(22) C(25) 65.3(4) . . . . yes O(2) C(1) O(1) C(3) -167.2(3) . . . . yes O(2) C(1) N(1) C(2) -170.5(3) . . . . yes O(2) C(1) N(1) C(4) 7.4(6) . . . . yes O(3) C(2) N(1) C(1) -135.3(3) . . . . yes O(3) C(2) N(1) C(4) 46.9(4) . . . . yes O(3) C(2) C(3) C(16) -96.5(3) . . . . yes O(3) C(2) C(3) C(22) 32.5(3) . . . . yes O(3) C(2) C(10) C(11) -149.7(3) . . . . yes O(3) C(2) C(10) C(15) 31.2(4) . . . . yes N(1) C(1) O(1) C(3) 16.1(3) . . . . yes N(1) C(2) C(3) C(16) 146.4(3) . . . . yes N(1) C(2) C(3) C(22) -84.6(3) . . . . yes N(1) C(2) C(10) C(11) -22.4(4) . . . . yes N(1) C(2) C(10) C(15) 158.6(3) . . . . yes N(1) C(4) C(5) C(6) 179.0(3) . . . . yes N(1) C(4) C(9) C(8) -176.8(3) . . . . yes C(1) O(1) C(3) C(2) -29.6(3) . . . . yes C(1) O(1) C(3) C(16) -149.0(3) . . . . yes C(1) O(1) C(3) C(22) 90.5(3) . . . . yes C(1) N(1) C(2) C(3) -22.9(3) . . . . yes C(1) N(1) C(2) C(10) 96.8(3) . . . . yes C(1) N(1) C(4) C(5) 27.6(5) . . . . yes C(1) N(1) C(4) C(9) -153.5(3) . . . . yes C(2) N(1) C(4) C(5) -154.8(3) . . . . yes C(2) N(1) C(4) C(9) 24.1(5) . . . . yes C(2) C(3) C(16) C(17) -108.1(3) . . . . yes C(2) C(3) C(16) C(21) 73.1(4) . . . . yes C(2) C(3) C(22) C(23) 50.4(4) . . . . yes C(2) C(3) C(22) C(25) 176.7(3) . . . . yes C(2) C(10) C(11) C(12) 179.2(4) . . . . yes C(2) C(10) C(15) C(14) -179.9(4) . . . . yes C(3) C(2) N(1) C(4) 159.3(3) . . . . yes C(3) C(2) C(10) C(11) 87.2(4) . . . . yes C(3) C(2) C(10) C(15) -91.8(3) . . . . yes C(3) C(16) C(17) C(18) -179.5(4) . . . . yes C(3) C(16) C(21) C(20) 179.8(4) . . . . yes C(3) C(22) C(23) C(24) 97.2(5) . . . . yes C(4) N(1) C(2) C(10) -81.0(3) . . . . yes C(4) C(5) C(6) C(7) -1.7(6) . . . . yes C(4) C(9) C(8) C(7) -2.7(6) . . . . yes C(5) C(4) C(9) C(8) 2.1(5) . . . . yes C(5) C(6) C(7) C(8) 1.1(6) . . . . yes C(6) C(5) C(4) C(9) 0.1(5) . . . . yes C(6) C(7) C(8) C(9) 1.1(6) . . . . yes C(10) C(2) C(3) C(16) 30.2(3) . . . . yes C(10) C(2) C(3) C(22) 159.2(3) . . . . yes C(10) C(11) C(12) C(13) 0.8(7) . . . . yes C(10) C(15) C(14) C(13) 0.9(7) . . . . yes C(11) C(10) C(15) C(14) 1.0(6) . . . . yes C(11) C(12) C(13) C(14) 1.1(8) . . . . yes C(12) C(11) C(10) C(15) -1.8(6) . . . . yes C(12) C(13) C(14) C(15) -1.9(8) . . . . yes C(16) C(3) C(22) C(23) -179.8(3) . . . . yes C(16) C(3) C(22) C(25) -53.5(4) . . . . yes C(16) C(17) C(18) C(19) 0.1(7) . . . . yes C(16) C(21) C(20) C(19) -0.5(7) . . . . yes C(17) C(16) C(3) C(22) 121.4(4) . . . . yes C(17) C(16) C(21) C(20) 0.9(6) . . . . yes C(17) C(18) C(19) C(20) 0.3(8) . . . . yes C(18) C(17) C(16) C(21) -0.7(6) . . . . yes C(18) C(19) C(20) C(21) -0.1(8) . . . . yes C(21) C(16) C(3) C(22) -57.4(4) . . . . yes C(24) C(23) C(22) C(25) -28.2(6) . . . . yes C(24) C(23) C(22) C(25) -28.2(6) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(15) 3.299(4) . 1_655 ? O(1) O(3) 3.468(3) . 1_655 ? O(2) O(3) 2.748(3) . 1_655 ? O(2) C(9) 3.162(4) . 1_655 ? O(2) C(15) 3.267(4) . 1_655 ? O(2) C(24) 3.530(6) . 4_554 ? O(2) C(10) 3.576(4) . 1_655 ? O(2) C(2) 3.598(3) . 1_655 ? O(3) C(1) 3.452(3) . 1_455 ? C(18) C(18) 3.535(10) . 3_665 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_site_distance_DH _geom_hbond_site_distance_HA _geom_hbond_site_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(3) H(1) O(1) . . 1_455 0.69(4) 3.08(4) 3.468(2) 118(4) no O(3) H(1) O(2) . . 1_455 0.69(4) 2.09(4) 2.748(2) 158(5) no #------------------------------------------------------------------------------