# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_C10H11ClN2O _database_code_depnum_ccdc_archive 'CCDC 873375' #TrackingRef 'MCano.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl N2 O' _chemical_formula_weight 210.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.9981(19) _cell_length_b 7.3161(12) _cell_length_c 23.079(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2025.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1087 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 20.87 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11540 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_sigmaI/netI 0.1026 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2138 _reflns_number_gt 943 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2138 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 0.41701(6) 1.20070(11) 0.55620(4) 0.0550(3) Uani 1 1 d . . . N1 N 0.2998(2) 1.0117(3) 0.45715(11) 0.0452(7) Uani 1 1 d . . . H1 H 0.3292 1.0689 0.4890 0.054 Uiso 1 1 d R . . O1 O 0.45072(16) 0.7443(3) 0.14426(10) 0.0480(6) Uani 1 1 d . . . N2 N 0.3605(2) 0.9714(3) 0.40968(11) 0.0396(7) Uani 1 1 d . . . H2 H 0.4334 0.9381 0.4155 0.048 Uiso 1 1 d R . . C3 C 0.2934(2) 0.9419(4) 0.36441(14) 0.0330(8) Uani 1 1 d . . . C4 C 0.1850(2) 0.9693(4) 0.38440(14) 0.0407(9) Uani 1 1 d . . . H4 H 0.1197 0.9590 0.3629 0.049 Uiso 1 1 calc R . . C5 C 0.1931(3) 1.0142(4) 0.44164(15) 0.0471(9) Uani 1 1 d . . . H5 H 0.1336 1.0420 0.4659 0.057 Uiso 1 1 calc R . . C6 C 0.3343(2) 0.8897(4) 0.30749(13) 0.0312(7) Uani 1 1 d . . . C7 C 0.4393(2) 0.8115(4) 0.29889(13) 0.0376(8) Uani 1 1 d . . . H7 H 0.4859 0.7915 0.3305 0.045 Uiso 1 1 calc R . . C8 C 0.4744(2) 0.7638(4) 0.24411(14) 0.0395(8) Uani 1 1 d . . . H8 H 0.5439 0.7096 0.2391 0.047 Uiso 1 1 calc R . . C9 C 0.4071(2) 0.7959(4) 0.19628(13) 0.0342(7) Uani 1 1 d . . . C10 C 0.3030(2) 0.8758(4) 0.20381(13) 0.0370(8) Uani 1 1 d . . . H10 H 0.2572 0.8981 0.1721 0.044 Uiso 1 1 calc R . . C11 C 0.2683(2) 0.9217(4) 0.25909(14) 0.0380(8) Uani 1 1 d . . . H11 H 0.1987 0.9756 0.2640 0.046 Uiso 1 1 calc R . . C12 C 0.3886(3) 0.7873(4) 0.09307(13) 0.0582(10) Uani 1 1 d . . . H13C H 0.3161 0.7321 0.0954 0.087 Uiso 1 1 calc R . . H12B H 0.4272 0.7412 0.0597 0.087 Uiso 1 1 calc R . . H12A H 0.3807 0.9175 0.0898 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl 0.0492(5) 0.0590(5) 0.0568(7) -0.0130(5) -0.0151(5) 0.0128(4) N1 0.0484(17) 0.0520(17) 0.035(2) -0.0097(13) -0.0005(15) -0.0007(14) O1 0.0473(14) 0.0641(15) 0.0325(15) -0.0030(12) 0.0028(12) 0.0047(10) N2 0.0316(14) 0.0468(15) 0.0404(19) -0.0065(14) -0.0030(14) 0.0032(12) C3 0.0308(17) 0.0329(17) 0.035(2) -0.0009(15) -0.0066(16) -0.0017(13) C4 0.0336(17) 0.050(2) 0.038(2) -0.0009(17) -0.0004(17) -0.0005(15) C5 0.040(2) 0.052(2) 0.049(3) -0.0016(19) 0.009(2) -0.0017(16) C6 0.0297(16) 0.0330(16) 0.031(2) -0.0013(14) -0.0007(16) -0.0020(13) C7 0.0328(17) 0.0377(17) 0.042(2) -0.0014(16) -0.0086(16) 0.0002(14) C8 0.0311(17) 0.0400(19) 0.048(2) -0.0028(17) 0.0007(17) 0.0011(14) C9 0.0350(17) 0.0337(16) 0.034(2) 0.0003(16) 0.0010(17) -0.0014(14) C10 0.0377(18) 0.0411(18) 0.032(2) 0.0073(16) -0.0060(16) 0.0024(15) C11 0.0299(17) 0.0418(19) 0.042(2) 0.0022(17) -0.0019(17) 0.0014(14) C12 0.076(3) 0.062(2) 0.037(2) -0.0004(19) 0.001(2) 0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.329(3) . ? N1 N2 1.348(3) . ? N1 H1 0.9175 . ? O1 C9 1.363(3) . ? O1 C12 1.432(3) . ? N2 C3 1.336(3) . ? N2 H2 0.9185 . ? C3 C4 1.395(4) . ? C3 C6 1.453(4) . ? C4 C5 1.365(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C11 1.389(3) . ? C6 C7 1.399(4) . ? C7 C8 1.377(3) . ? C7 H7 0.9300 . ? C8 C9 1.388(4) . ? C8 H8 0.9300 . ? C9 C10 1.389(4) . ? C10 C11 1.383(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H13C 0.9600 . ? C12 H12B 0.9600 . ? C12 H12A 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 N2 107.7(3) . . ? C5 N1 H1 125.5 . . ? N2 N1 H1 122.9 . . ? C9 O1 C12 117.7(2) . . ? C3 N2 N1 110.2(2) . . ? C3 N2 H2 130.2 . . ? N1 N2 H2 117.0 . . ? N2 C3 C4 106.2(3) . . ? N2 C3 C6 123.1(3) . . ? C4 C3 C6 130.7(3) . . ? C5 C4 C3 106.7(3) . . ? C5 C4 H4 126.6 . . ? C3 C4 H4 126.6 . . ? N1 C5 C4 109.1(3) . . ? N1 C5 H5 125.5 . . ? C4 C5 H5 125.5 . . ? C11 C6 C7 117.9(3) . . ? C11 C6 C3 119.4(3) . . ? C7 C6 C3 122.7(3) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.6(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? O1 C9 C8 115.5(3) . . ? O1 C9 C10 124.9(3) . . ? C8 C9 C10 119.7(3) . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C6 122.0(3) . . ? C10 C11 H11 119.0 . . ? C6 C11 H11 119.0 . . ? O1 C12 H13C 109.5 . . ? O1 C12 H12B 109.5 . . ? H13C C12 H12B 109.5 . . ? O1 C12 H12A 109.5 . . ? H13C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? 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 C5 N1 N2 C3 -2.1(3) . . . . ? N1 N2 C3 C4 1.4(3) . . . . ? N1 N2 C3 C6 -178.0(2) . . . . ? N2 C3 C4 C5 -0.2(3) . . . . ? C6 C3 C4 C5 179.1(3) . . . . ? N2 N1 C5 C4 2.0(3) . . . . ? C3 C4 C5 N1 -1.1(3) . . . . ? N2 C3 C6 C11 -158.0(3) . . . . ? C4 C3 C6 C11 22.8(4) . . . . ? N2 C3 C6 C7 20.5(4) . . . . ? C4 C3 C6 C7 -158.6(3) . . . . ? C11 C6 C7 C8 -1.6(4) . . . . ? C3 C6 C7 C8 179.8(2) . . . . ? C6 C7 C8 C9 1.3(4) . . . . ? C12 O1 C9 C8 -175.2(2) . . . . ? C12 O1 C9 C10 4.8(4) . . . . ? C7 C8 C9 O1 179.6(2) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? O1 C9 C10 C11 179.9(2) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C6 -0.2(4) . . . . ? C7 C6 C11 C10 1.1(4) . . . . ? C3 C6 C11 C10 179.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl 0.92 2.11 3.019(3) 172.4 . N2 H2 Cl 0.92 2.16 3.055(2) 163.6 5_676 C4 H4 O1 0.93 2.57 3.324(4) 138.4 6_556 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.226 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.053 data_C19H29BF4N2O _database_code_depnum_ccdc_archive 'CCDC 873376' #TrackingRef 'MCano.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H29 B F4 N2 O' _chemical_formula_weight 388.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1620(6) _cell_length_b 9.2230(9) _cell_length_c 19.0670(19) _cell_angle_alpha 93.895(2) _cell_angle_beta 94.406(2) _cell_angle_gamma 104.332(2) _cell_volume 1042.54(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1700 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 22.62 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7996 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3571 _reflns_number_gt 1749 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3571 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.2181 _refine_ls_wR_factor_gt 0.1841 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.0897(4) 0.6543(3) 0.41548(13) 0.0632(7) Uani 1 1 d . . . H1 H -0.1281 0.5370 0.4046 0.147(16) Uiso 1 1 d R . . N2 N -0.2333(5) 0.7188(3) 0.44860(14) 0.0702(8) Uani 1 1 d . . . H2 H -0.3467 0.6461 0.4795 0.157(18) Uiso 1 1 d R . . O1 O 0.7054(3) 0.6171(2) 0.22238(11) 0.0698(7) Uani 1 1 d . . . C3 C -0.1811(6) 0.8626(4) 0.43923(17) 0.0716(10) Uani 1 1 d . . . H3 H -0.2547 0.9321 0.4567 0.086 Uiso 1 1 calc R . . C4 C -0.0012(5) 0.8942(4) 0.39966(17) 0.0681(9) Uani 1 1 d . . . H4 H 0.0697 0.9877 0.3859 0.082 Uiso 1 1 calc R . . C5 C 0.0541(5) 0.7598(3) 0.38428(16) 0.0578(8) Uani 1 1 d . . . C6 C 0.2274(5) 0.7244(3) 0.34366(15) 0.0540(8) Uani 1 1 d . . . C7 C 0.3627(5) 0.8346(3) 0.30907(17) 0.0617(8) Uani 1 1 d . . . H7 H 0.3441 0.9318 0.3136 0.074 Uiso 1 1 calc R . . C8 C 0.5237(5) 0.8044(3) 0.26826(17) 0.0626(9) Uani 1 1 d . . . H8 H 0.6118 0.8801 0.2453 0.075 Uiso 1 1 calc R . . C9 C 0.5534(5) 0.6611(3) 0.26179(16) 0.0571(8) Uani 1 1 d . . . C10 C 0.4210(5) 0.5500(3) 0.29706(16) 0.0625(9) Uani 1 1 d . . . H10 H 0.4421 0.4534 0.2933 0.075 Uiso 1 1 calc R . . C11 C 0.2615(5) 0.5800(3) 0.33696(16) 0.0591(8) Uani 1 1 d . . . H11 H 0.1743 0.5040 0.3600 0.071 Uiso 1 1 calc R . . C12 C 0.8448(5) 0.7266(3) 0.18428(16) 0.0634(9) Uani 1 1 d . . . H12A H 0.9387 0.8070 0.2169 0.076 Uiso 1 1 calc R . . H12B H 0.7522 0.7694 0.1525 0.076 Uiso 1 1 calc R . . C13 C 0.9882(5) 0.6498(4) 0.14334(17) 0.0643(9) Uani 1 1 d . . . H13A H 0.8920 0.5680 0.1119 0.077 Uiso 1 1 calc R . . H13B H 1.0790 0.6070 0.1758 0.077 Uiso 1 1 calc R . . C14 C 1.1419(5) 0.7561(3) 0.10016(16) 0.0655(9) Uani 1 1 d . . . H14A H 1.0509 0.8022 0.0694 0.079 Uiso 1 1 calc R . . H14B H 1.2415 0.8355 0.1320 0.079 Uiso 1 1 calc R . . C15 C 1.2826(5) 0.6807(4) 0.05563(16) 0.0659(9) Uani 1 1 d . . . H15A H 1.1828 0.6018 0.0236 0.079 Uiso 1 1 calc R . . H15B H 1.3725 0.6337 0.0864 0.079 Uiso 1 1 calc R . . C16 C 1.4374(5) 0.7859(4) 0.01298(17) 0.0693(9) Uani 1 1 d . . . H16A H 1.3481 0.8359 -0.0162 0.083 Uiso 1 1 calc R . . H16B H 1.5411 0.8624 0.0452 0.083 Uiso 1 1 calc R . . C17 C 1.5716(5) 0.7111(4) -0.03380(17) 0.0708(9) Uani 1 1 d . . . H17A H 1.4679 0.6337 -0.0656 0.085 Uiso 1 1 calc R . . H17B H 1.6621 0.6619 -0.0045 0.085 Uiso 1 1 calc R . . C18 C 1.7258(6) 0.8157(4) -0.07742(18) 0.0761(10) Uani 1 1 d . . . H18A H 1.6357 0.8666 -0.1059 0.091 Uiso 1 1 calc R . . H18B H 1.8316 0.8917 -0.0455 0.091 Uiso 1 1 calc R . . C19 C 1.8559(6) 0.7414(4) -0.12526(19) 0.0835(11) Uani 1 1 d . . . H19A H 1.7502 0.6634 -0.1561 0.100 Uiso 1 1 calc R . . H19B H 1.9492 0.6930 -0.0966 0.100 Uiso 1 1 calc R . . C20 C 2.0038(7) 0.8433(4) -0.1702(2) 0.1062(14) Uani 1 1 d . . . H20A H 1.9101 0.8901 -0.1995 0.127 Uiso 1 1 calc R . . H20B H 2.1073 0.9227 -0.1393 0.127 Uiso 1 1 calc R . . C21 C 2.1376(8) 0.7705(5) -0.2168(3) 0.1381(19) Uani 1 1 d . . . H21A H 2.2284 0.7211 -0.1887 0.207 Uiso 1 1 calc R . . H21B H 2.2330 0.8456 -0.2410 0.207 Uiso 1 1 calc R . . H21C H 2.0374 0.6981 -0.2507 0.207 Uiso 1 1 calc R . . B1 B -0.3708(8) 0.2740(4) 0.4254(2) 0.0722(11) Uani 1 1 d . . . F1 F -0.4410(4) 0.3857(2) 0.46148(14) 0.1325(10) Uani 1 1 d . . . F4 F -0.3742(5) 0.1611(3) 0.46620(14) 0.1337(10) Uani 1 1 d . . . F3 F -0.5155(5) 0.2223(3) 0.36777(16) 0.1625(13) Uani 1 1 d . . . F2 F -0.1688(5) 0.3405(3) 0.40682(18) 0.1603(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0547(15) 0.0642(18) 0.0703(17) 0.0017(14) 0.0148(14) 0.0128(14) N2 0.0633(17) 0.074(2) 0.0715(18) -0.0025(16) 0.0131(15) 0.0147(16) O1 0.0713(14) 0.0598(14) 0.0846(15) 0.0183(12) 0.0321(12) 0.0175(11) C3 0.067(2) 0.077(3) 0.072(2) -0.0135(19) 0.0027(18) 0.0256(19) C4 0.070(2) 0.059(2) 0.075(2) -0.0007(17) 0.0125(18) 0.0139(17) C5 0.0515(18) 0.059(2) 0.0574(18) -0.0002(16) 0.0002(15) 0.0076(16) C6 0.0496(17) 0.0548(18) 0.0567(18) 0.0025(15) 0.0049(15) 0.0124(14) C7 0.0602(19) 0.0485(18) 0.077(2) 0.0065(16) 0.0112(17) 0.0138(15) C8 0.0608(19) 0.0516(19) 0.076(2) 0.0123(16) 0.0150(17) 0.0106(15) C9 0.0551(18) 0.058(2) 0.0602(19) 0.0090(15) 0.0083(15) 0.0154(15) C10 0.071(2) 0.0501(18) 0.068(2) 0.0127(16) 0.0125(17) 0.0141(16) C11 0.0584(19) 0.056(2) 0.066(2) 0.0153(15) 0.0181(16) 0.0123(15) C12 0.0635(19) 0.0570(19) 0.070(2) 0.0177(16) 0.0162(17) 0.0104(16) C13 0.0642(19) 0.062(2) 0.068(2) 0.0091(16) 0.0148(17) 0.0162(16) C14 0.070(2) 0.0593(19) 0.068(2) 0.0108(16) 0.0162(17) 0.0139(16) C15 0.071(2) 0.0557(19) 0.069(2) 0.0056(16) 0.0162(17) 0.0098(16) C16 0.079(2) 0.0554(19) 0.074(2) 0.0106(17) 0.0213(18) 0.0125(17) C17 0.080(2) 0.0538(19) 0.077(2) 0.0077(17) 0.0238(18) 0.0086(17) C18 0.089(2) 0.059(2) 0.080(2) 0.0109(18) 0.0318(19) 0.0091(18) C19 0.096(3) 0.065(2) 0.086(2) 0.0069(19) 0.036(2) 0.007(2) C20 0.133(3) 0.075(3) 0.110(3) 0.011(2) 0.065(3) 0.008(2) C21 0.161(4) 0.102(4) 0.145(4) -0.007(3) 0.094(4) 0.001(3) B1 0.093(3) 0.045(2) 0.078(3) 0.005(2) 0.022(3) 0.014(2) F1 0.171(2) 0.0723(15) 0.170(2) 0.0111(15) 0.106(2) 0.0331(15) F4 0.184(2) 0.0863(16) 0.143(2) 0.0476(16) 0.0200(18) 0.0465(16) F3 0.212(3) 0.105(2) 0.148(2) 0.0112(18) -0.043(2) 0.018(2) F2 0.137(2) 0.0936(19) 0.259(4) 0.017(2) 0.122(2) 0.0157(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.353(3) . ? N1 C5 1.348(4) . ? N1 H1 1.0517 . ? N2 C3 1.313(4) . ? N2 H2 1.0819 . ? O1 C9 1.365(3) . ? O1 C12 1.432(3) . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.453(4) . ? C6 C7 1.385(4) . ? C6 C11 1.398(4) . ? C7 C8 1.376(4) . ? C7 H7 0.9300 . ? C8 C9 1.377(4) . ? C8 H8 0.9300 . ? C9 C10 1.390(4) . ? C10 C11 1.358(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.494(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.519(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.513(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.510(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.506(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.517(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.498(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.501(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.492(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? B1 F2 1.330(4) . ? B1 F3 1.341(5) . ? B1 F4 1.339(4) . ? B1 F1 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 109.2(3) . . ? N2 N1 H1 120.2 . . ? C5 N1 H1 127.9 . . ? C3 N2 N1 108.3(3) . . ? C3 N2 H2 136.0 . . ? N1 N2 H2 115.3 . . ? C9 O1 C12 118.3(2) . . ? N2 C3 C4 109.3(3) . . ? N2 C3 H3 125.3 . . ? C4 C3 H3 125.3 . . ? C3 C4 C5 106.5(3) . . ? C3 C4 H4 126.7 . . ? C5 C4 H4 126.7 . . ? N1 C5 C4 106.6(3) . . ? N1 C5 C6 122.2(3) . . ? C4 C5 C6 131.1(3) . . ? C7 C6 C11 117.8(3) . . ? C7 C6 C5 120.1(3) . . ? C11 C6 C5 122.0(3) . . ? C6 C7 C8 121.9(3) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 119.4(3) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? O1 C9 C8 124.9(3) . . ? O1 C9 C10 115.8(3) . . ? C8 C9 C10 119.3(3) . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C6 120.5(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? O1 C12 C13 108.0(2) . . ? O1 C12 H12A 110.1 . . ? C13 C12 H12A 110.1 . . ? O1 C12 H12B 110.1 . . ? C13 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C12 C13 C14 112.3(3) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 113.7(3) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C16 114.1(3) . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 114.6(3) . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? C15 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 114.9(3) . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C17 115.2(3) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C20 115.6(3) . . ? C18 C19 H19A 108.4 . . ? C20 C19 H19A 108.4 . . ? C18 C19 H19B 108.4 . . ? C20 C19 H19B 108.4 . . ? H19A C19 H19B 107.4 . . ? C21 C20 C19 115.8(3) . . ? C21 C20 H20A 108.3 . . ? C19 C20 H20A 108.3 . . ? C21 C20 H20B 108.3 . . ? C19 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? F2 B1 F3 110.2(4) . . ? F2 B1 F4 114.9(4) . . ? F3 B1 F4 108.6(3) . . ? F2 B1 F1 105.3(3) . . ? F3 B1 F1 108.1(4) . . ? F4 B1 F1 109.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 C3 -0.5(3) . . . . ? N1 N2 C3 C4 -0.1(3) . . . . ? N2 C3 C4 C5 0.6(3) . . . . ? N2 N1 C5 C4 0.8(3) . . . . ? N2 N1 C5 C6 -179.2(2) . . . . ? C3 C4 C5 N1 -0.9(3) . . . . ? C3 C4 C5 C6 179.2(3) . . . . ? N1 C5 C6 C7 176.2(3) . . . . ? C4 C5 C6 C7 -3.9(4) . . . . ? N1 C5 C6 C11 -2.8(4) . . . . ? C4 C5 C6 C11 177.2(3) . . . . ? C11 C6 C7 C8 1.1(4) . . . . ? C5 C6 C7 C8 -177.9(3) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? C12 O1 C9 C8 -0.4(4) . . . . ? C12 O1 C9 C10 179.4(2) . . . . ? C7 C8 C9 O1 179.3(3) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? O1 C9 C10 C11 -178.9(3) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C6 -0.2(4) . . . . ? C7 C6 C11 C10 -0.7(4) . . . . ? C5 C6 C11 C10 178.3(3) . . . . ? C9 O1 C12 C13 -177.6(2) . . . . ? O1 C12 C13 C14 179.4(2) . . . . ? C12 C13 C14 C15 -177.6(3) . . . . ? C13 C14 C15 C16 -179.5(3) . . . . ? C14 C15 C16 C17 -177.7(3) . . . . ? C15 C16 C17 C18 179.4(3) . . . . ? C16 C17 C18 C19 -178.7(3) . . . . ? C17 C18 C19 C20 178.3(3) . . . . ? C18 C19 C20 C21 178.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 F2 1.05 1.77 2.805(4) 166.8 . N2 H2 F1 1.08 1.77 2.774(4) 151.7 2_466 C3 H3 F4 0.93 2.40 3.283(5) 157.9 1_565 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.376 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.040 data_C10H11N2O5Re _database_code_depnum_ccdc_archive 'CCDC 873377' #TrackingRef 'MCano.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 N2 O5 Re' _chemical_formula_weight 425.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.9991(4) _cell_length_b 9.5975(8) _cell_length_c 24.980(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1198.50(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6278 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.16 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 10.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3112 _exptl_absorpt_correction_T_max 0.6868 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9617 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2343 _reflns_number_gt 2244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.040(14) _refine_ls_number_reflns 2343 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0475 _refine_ls_wR_factor_gt 0.0467 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 1.0344(9) 0.4853(4) 0.08482(17) 0.0285(10) Uani 1 1 d . . . H2 H 1.0820 0.3984 0.0939 0.050 Uiso 1 1 d . . . N1 N 1.1945(10) 0.5573(4) 0.05132(16) 0.0313(9) Uani 1 1 d . . . H1 H 1.3147 0.5348 0.0228 0.050 Uiso 1 1 d . . . C5 C 1.1262(11) 0.6888(5) 0.0540(3) 0.0383(14) Uani 1 1 d . . . H5A H 1.2098 0.7608 0.0356 0.046 Uiso 1 1 calc R . . C4 C 0.9125(12) 0.7049(6) 0.0883(2) 0.0338(12) Uani 1 1 d . . . H4A H 0.8223 0.7871 0.0962 0.041 Uiso 1 1 calc R . . C3 C 0.8593(9) 0.5713(5) 0.10860(19) 0.0250(11) Uani 1 1 d . . . C6 C 0.6620(11) 0.5232(5) 0.14774(19) 0.0259(11) Uani 1 1 d . . . C7 C 0.5029(10) 0.6207(5) 0.1742(2) 0.0329(12) Uani 1 1 d . . . H7A H 0.5204 0.7149 0.1662 0.039 Uiso 1 1 calc R . . C8 C 0.3173(12) 0.5774(5) 0.2126(2) 0.0361(11) Uani 1 1 d . . . H8A H 0.2134 0.6428 0.2306 0.043 Uiso 1 1 calc R . . C9 C 0.2887(12) 0.4367(6) 0.2238(2) 0.0338(12) Uani 1 1 d . . . C10 C 0.4416(13) 0.3402(6) 0.1957(2) 0.0351(12) Uani 1 1 d . . . H10A H 0.4174 0.2458 0.2026 0.042 Uiso 1 1 calc R . . C11 C 0.6292(11) 0.3804(5) 0.1578(2) 0.0319(13) Uani 1 1 d . . . H11A H 0.7303 0.3145 0.1395 0.038 Uiso 1 1 calc R . . C12 C -0.0320(16) 0.4758(9) 0.2935(3) 0.064(2) Uani 1 1 d . . . H12A H -0.1444 0.4240 0.3175 0.097 Uiso 1 1 calc R . . H12B H -0.1408 0.5344 0.2712 0.097 Uiso 1 1 calc R . . H12C H 0.0895 0.5324 0.3138 0.097 Uiso 1 1 calc R . . O1 O 1.5537(9) 0.1842(5) 0.02480(18) 0.0473(11) Uani 1 1 d . . . O2 O 1.4576(10) -0.0237(5) 0.09996(17) 0.0497(11) Uani 1 1 d . . . O3 O 1.1185(8) 0.0030(4) 0.01172(16) 0.0367(10) Uani 1 1 d . . . O4 O 1.1154(9) 0.2033(4) 0.09606(16) 0.0423(10) Uani 1 1 d . . . O5 O 0.1160(8) 0.3816(5) 0.26079(16) 0.0479(11) Uani 1 1 d . . . Re1 Re 1.30948(4) 0.09390(2) 0.057722(8) 0.02598(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.027(2) 0.025(2) 0.033(2) 0.0042(18) -0.0007(19) 0.0010(19) N1 0.032(2) 0.035(2) 0.027(2) 0.0059(17) 0.006(2) -0.0019(19) C5 0.037(3) 0.025(3) 0.053(4) -0.007(3) 0.007(3) 0.002(2) C4 0.040(3) 0.024(3) 0.037(3) -0.003(2) -0.001(3) 0.002(2) C3 0.024(3) 0.026(3) 0.025(2) -0.0054(19) -0.0038(18) 0.005(2) C6 0.028(3) 0.022(2) 0.028(2) -0.0013(19) -0.004(2) 0.002(2) C7 0.033(3) 0.028(3) 0.037(3) -0.005(2) -0.001(2) 0.004(2) C8 0.035(3) 0.038(3) 0.035(3) -0.005(2) 0.007(3) 0.004(3) C9 0.030(3) 0.044(3) 0.027(3) -0.001(2) -0.002(2) 0.001(3) C10 0.044(3) 0.026(3) 0.036(3) 0.004(2) 0.002(3) 0.001(3) C11 0.032(3) 0.031(3) 0.033(3) -0.007(2) 0.011(2) 0.007(2) C12 0.062(5) 0.085(5) 0.047(4) -0.001(4) 0.024(4) 0.010(4) O1 0.036(2) 0.048(3) 0.058(3) 0.012(2) 0.004(2) -0.008(2) O2 0.058(3) 0.043(2) 0.047(3) 0.006(2) -0.009(2) 0.015(2) O3 0.037(2) 0.030(2) 0.043(2) -0.0074(17) -0.0052(18) 0.0003(17) O4 0.055(3) 0.034(2) 0.038(2) -0.0089(18) 0.0070(19) 0.011(2) O5 0.039(3) 0.057(3) 0.048(2) 0.007(2) 0.0137(19) 0.001(2) Re1 0.02781(11) 0.01993(9) 0.03021(11) -0.00183(9) -0.00062(9) 0.00276(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C3 1.341(6) . ? N2 N1 1.348(6) . ? N2 H2 0.8965 . ? N1 C5 1.310(6) . ? N1 H1 0.9567 . ? C5 C4 1.377(8) . ? C5 H5A 0.9300 . ? C4 C3 1.405(7) . ? C4 H4A 0.9300 . ? C3 C6 1.464(7) . ? C6 C7 1.394(7) . ? C6 C11 1.403(7) . ? C7 C8 1.398(7) . ? C7 H7A 0.9300 . ? C8 C9 1.387(7) . ? C8 H8A 0.9300 . ? C9 O5 1.370(7) . ? C9 C10 1.390(8) . ? C10 C11 1.388(7) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 O5 1.425(8) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O1 Re1 1.708(4) . ? O2 Re1 1.713(4) . ? O3 Re1 1.730(4) . ? O4 Re1 1.721(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N2 N1 110.3(4) . . ? C3 N2 H2 129.3 . . ? N1 N2 H2 118.4 . . ? C5 N1 N2 107.9(5) . . ? C5 N1 H1 114.8 . . ? N2 N1 H1 136.0 . . ? N1 C5 C4 110.0(5) . . ? N1 C5 H5A 125.0 . . ? C4 C5 H5A 125.0 . . ? C5 C4 C3 105.6(5) . . ? C5 C4 H4A 127.2 . . ? C3 C4 H4A 127.2 . . ? N2 C3 C4 106.1(4) . . ? N2 C3 C6 122.8(4) . . ? C4 C3 C6 131.1(5) . . ? C7 C6 C11 120.3(5) . . ? C7 C6 C3 119.3(4) . . ? C11 C6 C3 120.4(4) . . ? C8 C7 C6 120.3(5) . . ? C8 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C9 C8 C7 119.8(5) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? O5 C9 C8 125.2(5) . . ? O5 C9 C10 115.5(5) . . ? C8 C9 C10 119.3(5) . . ? C11 C10 C9 122.1(5) . . ? C11 C10 H10A 119.0 . . ? C9 C10 H10A 119.0 . . ? C10 C11 C6 118.2(5) . . ? C10 C11 H11A 120.9 . . ? C6 C11 H11A 120.9 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 O5 C12 117.9(5) . . ? O1 Re1 O2 108.8(2) . . ? O1 Re1 O4 111.2(2) . . ? O2 Re1 O4 107.6(2) . . ? O1 Re1 O3 109.3(2) . . ? O2 Re1 O3 108.4(2) . . ? O4 Re1 O3 111.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 N1 C5 0.9(6) . . . . ? N2 N1 C5 C4 -2.1(7) . . . . ? N1 C5 C4 C3 2.3(7) . . . . ? N1 N2 C3 C4 0.5(6) . . . . ? N1 N2 C3 C6 -179.1(4) . . . . ? C5 C4 C3 N2 -1.7(6) . . . . ? C5 C4 C3 C6 177.9(5) . . . . ? N2 C3 C6 C7 174.4(5) . . . . ? C4 C3 C6 C7 -5.2(8) . . . . ? N2 C3 C6 C11 -6.9(7) . . . . ? C4 C3 C6 C11 173.5(6) . . . . ? C11 C6 C7 C8 2.7(8) . . . . ? C3 C6 C7 C8 -178.6(5) . . . . ? C6 C7 C8 C9 -1.0(8) . . . . ? C7 C8 C9 O5 179.4(5) . . . . ? C7 C8 C9 C10 -1.4(9) . . . . ? O5 C9 C10 C11 -178.7(5) . . . . ? C8 C9 C10 C11 2.1(9) . . . . ? C9 C10 C11 C6 -0.3(9) . . . . ? C7 C6 C11 C10 -2.1(8) . . . . ? C3 C6 C11 C10 179.2(5) . . . . ? C8 C9 O5 C12 -5.2(9) . . . . ? C10 C9 O5 C12 175.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C5 H5A O3 0.93 2.44 3.195(7) 138.1 1_565 N2 H2 O4 0.90 1.88 2.751(6) 163.2 . N1 H1 O3 0.96 1.78 2.703(6) 160.2 4 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.916 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.117 data_C11H11F3N2O4S _database_code_depnum_ccdc_archive 'CCDC 873378' #TrackingRef 'MCano.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 F3 N2 O4 S' _chemical_formula_weight 324.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.344(4) _cell_length_b 10.275(6) _cell_length_c 11.844(7) _cell_angle_alpha 70.910(10) _cell_angle_beta 83.266(12) _cell_angle_gamma 89.319(12) _cell_volume 724.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 830 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 19.30 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5594 _diffrn_reflns_av_R_equivalents 0.0959 _diffrn_reflns_av_sigmaI/netI 0.1272 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2489 _reflns_number_gt 1029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2489 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1514 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.4991(5) 0.4967(4) 0.8560(4) 0.1043(13) Uani 1 1 d . . . N1 N 0.3738(6) 0.7333(4) 0.9095(3) 0.0637(11) Uani 1 1 d . . . H1 H 0.4378 0.6434 0.8979 0.116(18) Uiso 1 1 d R . . N2 N 0.1897(6) 0.7237(4) 0.9819(4) 0.0689(12) Uani 1 1 d . . . H2 H 0.1254 0.6286 1.0361 0.17(3) Uiso 1 1 d R . . C3 C 0.1511(7) 0.8460(5) 0.9940(5) 0.0745(15) Uani 1 1 d . . . H3 H 0.0339 0.8670 1.0393 0.089 Uiso 1 1 calc R . . C4 C 0.3133(7) 0.9362(5) 0.9284(4) 0.0690(15) Uani 1 1 d . . . H4 H 0.3260 1.0288 0.9210 0.083 Uiso 1 1 calc R . . C5 C 0.4546(7) 0.8631(5) 0.8754(4) 0.0560(12) Uani 1 1 d . . . C6 C 0.6582(7) 0.9041(5) 0.8014(4) 0.0595(13) Uani 1 1 d . . . C7 C 0.7244(7) 1.0413(5) 0.7557(4) 0.0756(15) Uani 1 1 d . . . H7 H 0.6370 1.1077 0.7723 0.091 Uiso 1 1 calc R . . C8 C 0.9189(9) 1.0819(6) 0.6853(5) 0.0872(17) Uani 1 1 d . . . H8 H 0.9619 1.1743 0.6557 0.105 Uiso 1 1 calc R . . C9 C 1.0467(8) 0.9833(8) 0.6604(5) 0.0846(18) Uani 1 1 d . . . C10 C 0.9859(8) 0.8461(7) 0.7051(5) 0.0932(19) Uani 1 1 d . . . H10 H 1.0744 0.7804 0.6882 0.112 Uiso 1 1 calc R . . C11 C 0.7955(8) 0.8069(5) 0.7743(5) 0.0790(16) Uani 1 1 d . . . H11 H 0.7554 0.7140 0.8043 0.095 Uiso 1 1 calc R . . C12 C 1.3227(10) 1.1423(8) 0.5475(6) 0.136(3) Uani 1 1 d . . . H12A H 1.2262 1.1983 0.4965 0.204 Uiso 1 1 calc R . . H12B H 1.4592 1.1460 0.5018 0.204 Uiso 1 1 calc R . . H12C H 1.3361 1.1760 0.6130 0.204 Uiso 1 1 calc R . . C13 C 0.3242(16) 0.4784(8) 0.6781(7) 0.126(3) Uani 1 1 d . . . F1 F 0.1628(13) 0.4332(6) 0.6466(5) 0.222(3) Uani 1 1 d . . . F2 F 0.5026(9) 0.4317(5) 0.6336(4) 0.199(2) Uani 1 1 d . . . F3 F 0.3390(9) 0.6140(5) 0.6304(4) 0.187(2) Uani 1 1 d . . . O1 O 1.2457(6) 1.0076(5) 0.5925(4) 0.1165(15) Uani 1 1 d . . . O3 O 0.1214(5) 0.4766(3) 0.8804(3) 0.0897(12) Uani 1 1 d . . . O4 O 0.3288(5) 0.2801(3) 0.8738(3) 0.0913(12) Uani 1 1 d . . . S1 S 0.3167(2) 0.42614(13) 0.83967(12) 0.0675(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.082(3) 0.076(3) 0.175(4) -0.069(3) -0.011(2) -0.004(2) N1 0.064(3) 0.045(3) 0.082(3) -0.021(2) -0.004(2) 0.000(2) N2 0.065(3) 0.048(3) 0.089(3) -0.019(2) 0.000(2) -0.005(2) C3 0.061(3) 0.056(3) 0.106(4) -0.031(3) 0.010(3) -0.002(3) C4 0.057(3) 0.053(3) 0.106(4) -0.040(3) -0.003(3) -0.003(2) C5 0.055(3) 0.044(3) 0.070(3) -0.019(3) -0.007(2) 0.001(2) C6 0.054(3) 0.056(3) 0.069(4) -0.020(3) -0.010(2) 0.000(2) C7 0.067(3) 0.063(4) 0.091(4) -0.019(3) -0.002(3) -0.009(3) C8 0.081(4) 0.079(4) 0.093(4) -0.019(3) -0.004(3) -0.021(3) C9 0.054(3) 0.126(6) 0.078(4) -0.042(4) 0.001(3) -0.014(4) C10 0.067(4) 0.103(5) 0.121(5) -0.058(4) 0.007(3) 0.002(3) C11 0.066(3) 0.079(4) 0.097(4) -0.038(3) -0.003(3) 0.001(3) C12 0.129(6) 0.139(7) 0.122(6) -0.021(5) 0.001(4) -0.047(5) C13 0.186(8) 0.082(6) 0.089(6) -0.013(5) 0.021(6) 0.018(5) F1 0.337(9) 0.199(6) 0.178(5) -0.089(4) -0.146(6) 0.026(5) F2 0.282(6) 0.179(4) 0.120(4) -0.059(3) 0.068(4) 0.045(4) F3 0.315(6) 0.101(3) 0.101(3) 0.009(3) 0.031(3) 0.022(3) O1 0.093(3) 0.134(4) 0.119(4) -0.045(3) 0.013(3) -0.025(3) O3 0.077(2) 0.068(2) 0.119(3) -0.039(2) 0.033(2) -0.0099(18) O4 0.119(3) 0.041(2) 0.111(3) -0.025(2) 0.001(2) -0.0012(18) S1 0.0811(10) 0.0457(8) 0.0745(10) -0.0247(7) 0.0115(7) -0.0079(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 S1 1.437(3) . ? N1 N2 1.350(5) . ? N1 C5 1.349(5) . ? N1 H1 1.0477 . ? N2 C3 1.327(5) . ? N2 H2 1.0352 . ? C3 C4 1.374(6) . ? C3 H3 0.9300 . ? C4 C5 1.387(6) . ? C4 H4 0.9300 . ? C5 C6 1.456(6) . ? C6 C7 1.385(6) . ? C6 C11 1.408(6) . ? C7 C8 1.391(6) . ? C7 H7 0.9300 . ? C8 C9 1.375(7) . ? C8 H8 0.9300 . ? C9 C10 1.376(7) . ? C9 O1 1.393(6) . ? C10 C11 1.363(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 O1 1.382(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 F1 1.272(9) . ? C13 F3 1.320(7) . ? C13 F2 1.342(8) . ? C13 S1 1.805(8) . ? O3 S1 1.430(3) . ? O4 S1 1.424(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 109.3(4) . . ? N2 N1 H1 118.9 . . ? C5 N1 H1 131.3 . . ? C3 N2 N1 108.6(4) . . ? C3 N2 H2 128.0 . . ? N1 N2 H2 120.7 . . ? N2 C3 C4 108.5(4) . . ? N2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? C3 C4 C5 107.0(4) . . ? C3 C4 H4 126.5 . . ? C5 C4 H4 126.5 . . ? N1 C5 C4 106.6(4) . . ? N1 C5 C6 122.3(4) . . ? C4 C5 C6 131.1(4) . . ? C7 C6 C11 117.5(4) . . ? C7 C6 C5 120.8(4) . . ? C11 C6 C5 121.8(4) . . ? C6 C7 C8 121.4(5) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 119.0(5) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 O1 113.3(6) . . ? C10 C9 C8 121.0(5) . . ? O1 C9 C8 125.7(6) . . ? C9 C10 C11 119.8(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 121.4(5) . . ? C10 C11 H11 119.3 . . ? C6 C11 H11 119.3 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? F1 C13 F3 109.9(8) . . ? F1 C13 F2 110.1(8) . . ? F3 C13 F2 105.7(7) . . ? F1 C13 S1 112.0(6) . . ? F3 C13 S1 110.6(6) . . ? F2 C13 S1 108.3(6) . . ? C12 O1 C9 117.2(5) . . ? O4 S1 O2 115.6(2) . . ? O4 S1 O3 115.5(2) . . ? O2 S1 O3 112.4(2) . . ? O4 S1 C13 103.1(3) . . ? O2 S1 C13 103.3(4) . . ? O3 S1 C13 105.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 C3 0.3(5) . . . . ? N1 N2 C3 C4 -0.1(6) . . . . ? N2 C3 C4 C5 -0.2(6) . . . . ? N2 N1 C5 C4 -0.4(5) . . . . ? N2 N1 C5 C6 177.0(4) . . . . ? C3 C4 C5 N1 0.4(5) . . . . ? C3 C4 C5 C6 -176.8(5) . . . . ? N1 C5 C6 C7 171.9(4) . . . . ? C4 C5 C6 C7 -11.3(8) . . . . ? N1 C5 C6 C11 -8.5(7) . . . . ? C4 C5 C6 C11 168.2(5) . . . . ? C11 C6 C7 C8 0.1(7) . . . . ? C5 C6 C7 C8 179.7(5) . . . . ? C6 C7 C8 C9 0.5(8) . . . . ? C7 C8 C9 C10 -0.9(9) . . . . ? C7 C8 C9 O1 -179.4(5) . . . . ? O1 C9 C10 C11 179.3(5) . . . . ? C8 C9 C10 C11 0.6(9) . . . . ? C9 C10 C11 C6 0.0(9) . . . . ? C7 C6 C11 C10 -0.4(8) . . . . ? C5 C6 C11 C10 -179.9(5) . . . . ? C10 C9 O1 C12 -177.8(6) . . . . ? C8 C9 O1 C12 0.9(8) . . . . ? F1 C13 S1 O4 64.3(7) . . . . ? F3 C13 S1 O4 -172.8(6) . . . . ? F2 C13 S1 O4 -57.4(7) . . . . ? F1 C13 S1 O2 -175.1(6) . . . . ? F3 C13 S1 O2 -52.1(7) . . . . ? F2 C13 S1 O2 63.3(7) . . . . ? F1 C13 S1 O3 -57.1(7) . . . . ? F3 C13 S1 O3 65.9(7) . . . . ? F2 C13 S1 O3 -178.7(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 1.05 1.76 2.791(5) 166.6 . N2 H2 O3 1.04 1.89 2.817(5) 147.2 2_567 C4 H4 O4 0.93 2.46 3.378(6) 171.0 1_565 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.331 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.061 data_C17H18N2O4S _database_code_depnum_ccdc_archive 'CCDC 873379' #TrackingRef 'MCano.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O4 S' _chemical_formula_weight 346.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9935(18) _cell_length_b 14.007(3) _cell_length_c 18.935(3) _cell_angle_alpha 103.999(4) _cell_angle_beta 91.508(4) _cell_angle_gamma 96.957(4) _cell_volume 2548.5(8) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1565 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 20.84 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19528 _diffrn_reflns_av_R_equivalents 0.1040 _diffrn_reflns_av_sigmaI/netI 0.2075 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8734 _reflns_number_gt 2671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0050P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8734 _refine_ls_number_parameters 655 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2109 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C3 C 0.3249(6) 0.4864(4) 0.1167(3) 0.0454(18) Uani 1 1 d . . . H3A H 0.3642 0.5251 0.1611 0.055 Uiso 1 1 calc R . . C4 C 0.3919(5) 0.4409(4) 0.0586(3) 0.0391(17) Uani 1 1 d . . . H4A H 0.4850 0.4426 0.0562 0.047 Uiso 1 1 calc R . . C5 C 0.2957(6) 0.3921(4) 0.0039(3) 0.0321(16) Uani 1 1 d . . . C6 C 0.3098(6) 0.3346(4) -0.0695(3) 0.0325(16) Uani 1 1 d . . . C7 C 0.4359(6) 0.3117(4) -0.0909(3) 0.0436(17) Uani 1 1 d . . . H7A H 0.5098 0.3333 -0.0576 0.052 Uiso 1 1 calc R . . C8 C 0.4549(5) 0.2572(4) -0.1609(3) 0.0452(17) Uani 1 1 d . . . H8A H 0.5412 0.2448 -0.1744 0.054 Uiso 1 1 calc R . . C9 C 0.3458(6) 0.2216(4) -0.2101(3) 0.0456(18) Uani 1 1 d . . . C10 C 0.2173(6) 0.2434(4) -0.1884(3) 0.0518(19) Uani 1 1 d . . . H10A H 0.1424 0.2193 -0.2209 0.062 Uiso 1 1 calc R . . C11 C 0.2014(6) 0.2998(4) -0.1200(3) 0.0497(19) Uani 1 1 d . . . H11A H 0.1159 0.3150 -0.1071 0.060 Uiso 1 1 calc R . . C12 C 0.4820(5) 0.1458(4) -0.3050(3) 0.071(2) Uani 1 1 d . . . H12A H 0.4718 0.1062 -0.3543 0.107 Uiso 1 1 calc R . . H12B H 0.5233 0.1104 -0.2745 0.107 Uiso 1 1 calc R . . H12C H 0.5381 0.2072 -0.3030 0.107 Uiso 1 1 calc R . . C13 C -0.2333(5) 0.2538(4) 0.0777(3) 0.0403(16) Uani 1 1 d . . . C14 C -0.2381(6) 0.2523(5) 0.1484(3) 0.061(2) Uani 1 1 d . . . H14A H -0.2044 0.3087 0.1844 0.073 Uiso 1 1 calc R . . C15 C -0.2930(7) 0.1670(6) 0.1679(4) 0.076(2) Uani 1 1 d . . . H15A H -0.2986 0.1681 0.2170 0.092 Uiso 1 1 calc R . . C16 C -0.3393(7) 0.0809(6) 0.1161(5) 0.079(2) Uani 1 1 d . . . C17 C -0.3343(7) 0.0827(5) 0.0419(4) 0.095(3) Uani 1 1 d . . . H17A H -0.3654 0.0263 0.0053 0.114 Uiso 1 1 calc R . . C18 C -0.2816(6) 0.1709(5) 0.0243(3) 0.068(2) Uani 1 1 d . . . H18A H -0.2793 0.1731 -0.0244 0.082 Uiso 1 1 calc R . . C19 C -0.4043(7) -0.0160(5) 0.1334(4) 0.131(3) Uani 1 1 d . . . H19A H -0.4020 -0.0078 0.1852 0.197 Uiso 1 1 calc R . . H19B H -0.3551 -0.0693 0.1116 0.197 Uiso 1 1 calc R . . H19C H -0.4963 -0.0310 0.1140 0.197 Uiso 1 1 calc R . . C20 C -0.3286(6) 0.5188(4) 0.2226(3) 0.0468(18) Uani 1 1 d . . . H20A H -0.3717 0.4842 0.1780 0.056 Uiso 1 1 calc R . . C21 C -0.3907(5) 0.5665(4) 0.2833(3) 0.0412(17) Uani 1 1 d . . . H21A H -0.4826 0.5703 0.2868 0.049 Uiso 1 1 calc R . . C22 C -0.2904(6) 0.6074(4) 0.3376(3) 0.0316(16) Uani 1 1 d . . . C23 C -0.2992(6) 0.6659(4) 0.4113(3) 0.0334(17) Uani 1 1 d . . . C24 C -0.4233(5) 0.6933(4) 0.4359(3) 0.0445(17) Uani 1 1 d . . . H24A H -0.4999 0.6738 0.4043 0.053 Uiso 1 1 calc R . . C25 C -0.4343(6) 0.7490(4) 0.5061(3) 0.0518(19) Uani 1 1 d . . . H25A H -0.5177 0.7662 0.5213 0.062 Uiso 1 1 calc R . . C26 C -0.3220(7) 0.7788(5) 0.5534(3) 0.0466(18) Uani 1 1 d . . . C27 C -0.1987(6) 0.7526(4) 0.5305(3) 0.0501(19) Uani 1 1 d . . . H27A H -0.1225 0.7730 0.5623 0.060 Uiso 1 1 calc R . . C28 C -0.1875(6) 0.6970(4) 0.4612(3) 0.0459(18) Uani 1 1 d . . . H28A H -0.1036 0.6794 0.4470 0.055 Uiso 1 1 calc R . . C29 C -0.4500(6) 0.8572(5) 0.6497(3) 0.091(3) Uani 1 1 d . . . H29A H -0.4375 0.8963 0.6992 0.137 Uiso 1 1 calc R . . H29B H -0.5085 0.7969 0.6478 0.137 Uiso 1 1 calc R . . H29C H -0.4898 0.8941 0.6199 0.137 Uiso 1 1 calc R . . C47 C -0.1690(5) 0.2401(5) 0.4009(3) 0.0436(18) Uani 1 1 d . . . C48 C -0.1399(6) 0.1637(5) 0.3465(3) 0.0569(19) Uani 1 1 d . . . H48A H -0.1179 0.1748 0.3014 0.068 Uiso 1 1 calc R . . C49 C -0.1429(7) 0.0698(6) 0.3578(4) 0.078(2) Uani 1 1 d . . . H49A H -0.1241 0.0185 0.3195 0.094 Uiso 1 1 calc R . . C50 C -0.1726(8) 0.0489(7) 0.4231(5) 0.089(3) Uani 1 1 d . . . C51 C -0.2039(7) 0.1285(7) 0.4782(4) 0.093(3) Uani 1 1 d . . . H51A H -0.2280 0.1174 0.5230 0.111 Uiso 1 1 calc R . . C52 C -0.1999(7) 0.2231(6) 0.4676(4) 0.074(2) Uani 1 1 d . . . H52A H -0.2180 0.2752 0.5055 0.089 Uiso 1 1 calc R . . C53 C -0.1710(7) -0.0536(5) 0.4372(4) 0.140(4) Uani 1 1 d . . . H53A H -0.1478 -0.0987 0.3938 0.210 Uiso 1 1 calc R . . H53B H -0.2587 -0.0770 0.4505 0.210 Uiso 1 1 calc R . . H53C H -0.1055 -0.0496 0.4761 0.210 Uiso 1 1 calc R . . C37 C 0.3355(6) 0.4821(4) 0.4394(3) 0.0461(18) Uani 1 1 d . . . H37A H 0.3856 0.5176 0.4817 0.055 Uiso 1 1 calc R . . C38 C 0.3867(6) 0.4297(4) 0.3772(4) 0.0494(19) Uani 1 1 d . . . H38A H 0.4765 0.4213 0.3697 0.059 Uiso 1 1 calc R . . C39 C 0.2767(6) 0.3921(4) 0.3278(3) 0.0351(17) Uani 1 1 d . . . C40 C 0.2691(6) 0.3310(4) 0.2528(3) 0.0409(18) Uani 1 1 d . . . C41 C 0.3830(6) 0.2981(4) 0.2196(3) 0.0512(19) Uani 1 1 d . . . H41A H 0.4663 0.3143 0.2456 0.061 Uiso 1 1 calc R . . C42 C 0.3742(6) 0.2420(5) 0.1487(4) 0.057(2) Uani 1 1 d . . . H42A H 0.4520 0.2222 0.1270 0.068 Uiso 1 1 calc R . . C43 C 0.2521(7) 0.2147(5) 0.1096(3) 0.0523(19) Uani 1 1 d . . . C44 C 0.1385(6) 0.2465(4) 0.1414(3) 0.0513(18) Uani 1 1 d . . . H44A H 0.0552 0.2300 0.1155 0.062 Uiso 1 1 calc R . . C45 C 0.1489(6) 0.3025(5) 0.2113(3) 0.0526(19) Uani 1 1 d . . . H45A H 0.0706 0.3226 0.2323 0.063 Uiso 1 1 calc R . . C46 C 0.1297(6) 0.1260(4) -0.0022(3) 0.079(2) Uani 1 1 d . . . H46A H 0.1453 0.0862 -0.0494 0.118 Uiso 1 1 calc R . . H46B H 0.0908 0.1834 -0.0077 0.118 Uiso 1 1 calc R . . H46C H 0.0688 0.0878 0.0220 0.118 Uiso 1 1 calc R . . C30 C 0.1520(5) 0.7480(4) 0.2625(3) 0.0354(16) Uani 1 1 d . . . C31 C 0.1443(6) 0.8339(5) 0.3146(3) 0.068(2) Uani 1 1 d . . . H31A H 0.1402 0.8317 0.3632 0.081 Uiso 1 1 calc R . . C32 C 0.1425(6) 0.9244(5) 0.2965(4) 0.072(2) Uani 1 1 d . . . H32A H 0.1417 0.9818 0.3333 0.087 Uiso 1 1 calc R . . C33 C 0.1420(7) 0.9301(5) 0.2255(4) 0.065(2) Uani 1 1 d . . . C34 C 0.1482(6) 0.8429(6) 0.1728(4) 0.065(2) Uani 1 1 d . . . H34A H 0.1479 0.8442 0.1239 0.078 Uiso 1 1 calc R . . C35 C 0.1551(5) 0.7538(5) 0.1915(3) 0.0545(19) Uani 1 1 d . . . H35 H 0.1619 0.6969 0.1551 0.065 Uiso 1 1 calc R . . C36 C 0.1331(7) 1.0275(5) 0.2047(4) 0.109(3) Uani 1 1 d . . . H36A H 0.1307 1.0796 0.2480 0.163 Uiso 1 1 calc R . . H36B H 0.0525 1.0215 0.1744 0.163 Uiso 1 1 calc R . . H36C H 0.2106 1.0429 0.1786 0.163 Uiso 1 1 calc R . . N1 N 0.1751(5) 0.4077(3) 0.0307(3) 0.0367(13) Uani 1 1 d . . . H1 H 0.0817 0.3957 0.0099 0.08(2) Uiso 1 1 d R . . N2 N 0.1932(5) 0.4653(3) 0.0984(3) 0.0422(15) Uani 1 1 d . . . H2 H 0.1294 0.4894 0.1337 0.07(2) Uiso 1 1 d R . . N3 N -0.1740(5) 0.5850(3) 0.3092(3) 0.0368(13) Uani 1 1 d . . . H3 H -0.0674 0.6011 0.3278 0.07(2) Uiso 1 1 d R . . N4 N -0.1943(5) 0.5316(4) 0.2395(3) 0.0426(15) Uani 1 1 d . . . H4 H -0.1206 0.5150 0.2061 0.32(6) Uiso 1 1 d R . . N5 N 0.1655(5) 0.4194(4) 0.3618(3) 0.0427(15) Uani 1 1 d . . . H5 H 0.0644 0.4067 0.3426 0.13(3) Uiso 1 1 d R . . N6 N 0.2025(5) 0.4730(4) 0.4288(3) 0.0457(15) Uani 1 1 d . . . H6 H 0.1338 0.4933 0.4599 0.034(15) Uiso 1 1 d R . . O1 O 0.3516(4) 0.1660(3) -0.2796(2) 0.0644(13) Uani 1 1 d . . . O2 O -0.0905(3) 0.4246(3) 0.11516(19) 0.0517(12) Uani 1 1 d . . . O3 O -0.2901(3) 0.4040(3) 0.0355(2) 0.0595(13) Uani 1 1 d . . . O4 O -0.0909(3) 0.3335(3) -0.00965(18) 0.0473(12) Uani 1 1 d . . . O5 O -0.3211(4) 0.8338(3) 0.6231(2) 0.0674(14) Uani 1 1 d . . . O10 O -0.0911(4) 0.4268(3) 0.4489(2) 0.0646(14) Uani 1 1 d . . . O11 O -0.3083(4) 0.3748(3) 0.3843(2) 0.0788(15) Uani 1 1 d . . . O12 O -0.1039(3) 0.3595(3) 0.3201(2) 0.0520(12) Uani 1 1 d . . . O9 O 0.2560(4) 0.1570(3) 0.0405(2) 0.0728(14) Uani 1 1 d . . . O6 O 0.0900(3) 0.5600(3) 0.2285(2) 0.0517(12) Uani 1 1 d . . . O7 O 0.3036(3) 0.6286(3) 0.2956(2) 0.0601(13) Uani 1 1 d . . . O8 O 0.0931(3) 0.6453(3) 0.35569(18) 0.0452(11) Uani 1 1 d . . . S1 S -0.17253(15) 0.36279(13) 0.05253(9) 0.0395(5) Uani 1 1 d . . . S3 S -0.17051(16) 0.35966(13) 0.38712(10) 0.0492(5) Uani 1 1 d . . . S2 S 0.16185(15) 0.63647(12) 0.28740(9) 0.0392(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.040(4) 0.046(5) 0.051(5) 0.018(4) 0.000(4) -0.002(4) C4 0.026(4) 0.049(5) 0.048(4) 0.019(4) 0.011(3) 0.011(3) C5 0.021(4) 0.039(4) 0.037(4) 0.011(3) 0.004(3) 0.006(3) C6 0.024(4) 0.037(4) 0.042(4) 0.018(3) 0.005(3) 0.007(3) C7 0.038(4) 0.041(4) 0.046(4) 0.003(3) 0.001(3) 0.001(3) C8 0.027(4) 0.051(5) 0.053(4) 0.004(4) 0.004(3) 0.006(3) C9 0.047(4) 0.038(5) 0.046(4) 0.003(4) 0.006(4) 0.000(4) C10 0.038(4) 0.059(5) 0.052(5) 0.006(4) -0.003(4) -0.001(4) C11 0.031(4) 0.059(5) 0.053(5) 0.003(4) 0.009(4) 0.003(4) C12 0.062(5) 0.089(6) 0.059(5) 0.004(4) 0.027(4) 0.017(4) C13 0.041(4) 0.046(4) 0.033(4) 0.008(3) 0.004(3) 0.006(3) C14 0.058(5) 0.075(6) 0.054(5) 0.032(4) -0.004(4) -0.004(4) C15 0.083(6) 0.087(7) 0.067(5) 0.031(5) 0.000(4) 0.018(5) C16 0.069(5) 0.075(7) 0.113(7) 0.052(6) 0.031(5) 0.024(5) C17 0.127(7) 0.043(5) 0.103(7) -0.002(5) 0.049(6) -0.006(5) C18 0.093(5) 0.062(5) 0.048(4) 0.013(4) 0.032(4) 0.000(4) C19 0.142(8) 0.086(6) 0.195(9) 0.089(7) 0.053(7) 0.012(6) C20 0.046(5) 0.054(5) 0.039(4) 0.009(4) 0.002(4) 0.005(4) C21 0.031(4) 0.049(5) 0.043(4) 0.013(4) 0.007(4) -0.001(3) C22 0.030(4) 0.032(4) 0.035(4) 0.014(3) 0.004(4) 0.002(3) C23 0.031(4) 0.026(4) 0.046(4) 0.012(3) 0.012(4) 0.005(3) C24 0.035(4) 0.053(5) 0.040(4) 0.004(4) 0.003(3) 0.001(3) C25 0.044(4) 0.061(5) 0.050(5) 0.009(4) 0.017(4) 0.012(4) C26 0.050(5) 0.040(5) 0.045(5) 0.000(4) 0.003(4) 0.013(4) C27 0.050(5) 0.051(5) 0.046(5) 0.006(4) 0.000(4) 0.004(4) C28 0.030(4) 0.051(5) 0.060(5) 0.020(4) 0.001(4) 0.004(3) C29 0.090(6) 0.095(6) 0.070(5) -0.021(4) 0.016(5) 0.021(5) C47 0.035(4) 0.047(5) 0.043(4) 0.003(4) -0.009(3) 0.002(3) C48 0.063(5) 0.049(5) 0.058(5) 0.011(4) -0.009(4) 0.013(4) C49 0.088(6) 0.053(6) 0.080(6) -0.002(5) -0.026(5) 0.005(5) C50 0.099(6) 0.093(8) 0.075(6) 0.046(6) -0.042(5) -0.030(6) C51 0.104(7) 0.125(9) 0.049(5) 0.038(6) -0.019(5) -0.010(7) C52 0.097(6) 0.079(7) 0.050(5) 0.027(5) 0.000(4) 0.001(5) C53 0.162(8) 0.082(7) 0.186(9) 0.090(7) -0.096(7) -0.040(6) C37 0.027(4) 0.060(5) 0.053(5) 0.021(4) -0.008(4) 0.001(4) C38 0.029(4) 0.063(5) 0.063(5) 0.026(4) 0.006(4) 0.008(4) C39 0.029(4) 0.038(4) 0.044(4) 0.016(4) 0.009(3) 0.013(3) C40 0.031(4) 0.038(4) 0.054(5) 0.008(4) 0.011(4) 0.008(3) C41 0.043(4) 0.053(5) 0.059(5) 0.012(4) 0.011(4) 0.016(3) C42 0.043(5) 0.066(5) 0.063(5) 0.012(4) 0.019(4) 0.021(4) C43 0.064(5) 0.046(5) 0.047(4) 0.009(4) 0.005(4) 0.009(4) C44 0.034(4) 0.059(5) 0.058(5) 0.005(4) 0.008(4) 0.012(3) C45 0.045(4) 0.066(5) 0.049(4) 0.016(4) 0.007(4) 0.017(4) C46 0.089(6) 0.070(5) 0.072(5) 0.000(4) 0.004(4) 0.021(4) C30 0.030(4) 0.039(4) 0.036(4) 0.004(4) 0.004(3) 0.010(3) C31 0.106(6) 0.062(6) 0.038(4) 0.012(4) 0.000(4) 0.023(5) C32 0.105(6) 0.050(6) 0.053(5) -0.003(4) -0.011(5) 0.014(5) C33 0.078(5) 0.047(5) 0.070(5) 0.016(5) -0.002(4) 0.001(4) C34 0.059(5) 0.089(6) 0.053(5) 0.033(5) 0.005(4) 0.004(5) C35 0.054(4) 0.065(6) 0.049(5) 0.013(4) 0.023(4) 0.019(4) C36 0.144(7) 0.064(6) 0.137(7) 0.061(6) -0.011(6) 0.018(5) N1 0.028(4) 0.035(3) 0.045(4) 0.006(3) 0.009(3) 0.000(2) N2 0.040(4) 0.044(4) 0.041(4) 0.008(3) 0.011(3) 0.003(3) N3 0.023(3) 0.043(4) 0.047(4) 0.016(3) 0.000(3) 0.003(3) N4 0.037(4) 0.054(4) 0.035(3) 0.011(3) 0.000(3) 0.002(3) N5 0.041(4) 0.051(4) 0.037(3) 0.008(3) 0.005(3) 0.011(3) N6 0.033(4) 0.056(4) 0.052(4) 0.014(3) 0.006(3) 0.014(3) O1 0.054(3) 0.066(3) 0.056(3) -0.014(3) 0.006(2) -0.003(2) O2 0.034(2) 0.061(3) 0.044(3) -0.014(2) 0.006(2) -0.004(2) O3 0.034(2) 0.069(3) 0.089(3) 0.041(3) -0.001(2) 0.016(2) O4 0.037(2) 0.069(3) 0.027(2) 0.001(2) 0.0097(19) -0.007(2) O5 0.073(3) 0.062(3) 0.054(3) -0.010(3) 0.013(3) 0.004(3) O10 0.049(3) 0.064(3) 0.065(3) -0.011(3) 0.011(2) -0.005(2) O11 0.030(3) 0.075(4) 0.134(4) 0.024(3) 0.017(3) 0.016(2) O12 0.040(2) 0.073(3) 0.044(3) 0.017(2) 0.007(2) 0.004(2) O9 0.072(3) 0.077(4) 0.060(3) -0.003(3) 0.002(3) 0.012(3) O6 0.040(3) 0.048(3) 0.053(3) -0.010(2) 0.003(2) -0.005(2) O7 0.024(2) 0.062(3) 0.100(4) 0.028(3) 0.011(2) 0.013(2) O8 0.038(2) 0.057(3) 0.038(2) 0.009(2) 0.000(2) 0.001(2) S1 0.0249(10) 0.0484(12) 0.0429(11) 0.0073(9) 0.0019(9) 0.0031(9) S3 0.0284(11) 0.0509(14) 0.0637(13) 0.0062(11) 0.0065(10) 0.0022(9) S2 0.0255(10) 0.0438(12) 0.0451(11) 0.0053(9) 0.0021(9) 0.0040(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 N2 1.331(6) . ? C3 C4 1.368(6) . ? C3 H3A 0.9300 . ? C4 C5 1.381(7) . ? C4 H4A 0.9300 . ? C5 N1 1.341(6) . ? C5 C6 1.448(7) . ? C6 C7 1.385(6) . ? C6 C11 1.385(7) . ? C7 C8 1.390(7) . ? C7 H7A 0.9300 . ? C8 C9 1.377(7) . ? C8 H8A 0.9300 . ? C9 O1 1.364(6) . ? C9 C10 1.405(7) . ? C10 C11 1.370(7) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 O1 1.438(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.346(7) . ? C13 C18 1.369(7) . ? C13 S1 1.752(6) . ? C14 C15 1.388(7) . ? C14 H14A 0.9300 . ? C15 C16 1.378(8) . ? C15 H15A 0.9300 . ? C16 C17 1.414(8) . ? C16 C19 1.544(8) . ? C17 C18 1.401(7) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N4 1.351(6) . ? C20 C21 1.385(6) . ? C20 H20A 0.9300 . ? C21 C22 1.384(7) . ? C21 H21A 0.9300 . ? C22 N3 1.335(6) . ? C22 C23 1.448(7) . ? C23 C28 1.399(7) . ? C23 C24 1.400(6) . ? C24 C25 1.384(7) . ? C24 H24A 0.9300 . ? C25 C26 1.373(7) . ? C25 H25A 0.9300 . ? C26 O5 1.357(6) . ? C26 C27 1.379(7) . ? C27 C28 1.370(7) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 O5 1.441(5) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C47 C48 1.360(7) . ? C47 C52 1.377(7) . ? C47 S3 1.757(6) . ? C48 C49 1.381(8) . ? C48 H48A 0.9300 . ? C49 C50 1.369(8) . ? C49 H49A 0.9300 . ? C50 C51 1.404(9) . ? C50 C53 1.524(9) . ? C51 C52 1.384(9) . ? C51 H51A 0.9300 . ? C52 H52A 0.9300 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C37 N6 1.325(6) . ? C37 C38 1.376(7) . ? C37 H37A 0.9300 . ? C38 C39 1.388(7) . ? C38 H38A 0.9300 . ? C39 N5 1.348(6) . ? C39 C40 1.464(7) . ? C40 C45 1.379(7) . ? C40 C41 1.388(6) . ? C41 C42 1.377(7) . ? C41 H41A 0.9300 . ? C42 C43 1.373(7) . ? C42 H42A 0.9300 . ? C43 C44 1.370(7) . ? C43 O9 1.366(6) . ? C44 C45 1.359(7) . ? C44 H44A 0.9300 . ? C45 H45A 0.9300 . ? C46 O9 1.442(6) . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C30 C31 1.370(7) . ? C30 C35 1.366(7) . ? C30 S2 1.751(6) . ? C31 C32 1.392(7) . ? C31 H31A 0.9300 . ? C32 C33 1.365(8) . ? C32 H32A 0.9300 . ? C33 C34 1.387(8) . ? C33 C36 1.520(7) . ? C34 C35 1.386(7) . ? C34 H34A 0.9300 . ? C35 H35 0.9300 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? N1 N2 1.333(5) . ? N1 H1 0.9824 . ? N2 H2 0.9665 . ? N3 N4 1.347(5) . ? N3 H3 1.0920 . ? N4 H4 0.9956 . ? N5 N6 1.326(6) . ? N5 H5 1.0448 . ? N6 H6 0.9415 . ? O2 S1 1.452(4) . ? O3 S1 1.432(3) . ? O4 S1 1.455(3) . ? O10 S3 1.456(4) . ? O11 S3 1.421(4) . ? O12 S3 1.448(3) . ? O6 S2 1.449(4) . ? O7 S2 1.442(3) . ? O8 S2 1.466(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C3 C4 107.7(6) . . ? N2 C3 H3A 126.2 . . ? C4 C3 H3A 126.2 . . ? C3 C4 C5 107.3(5) . . ? C3 C4 H4A 126.4 . . ? C5 C4 H4A 126.4 . . ? N1 C5 C4 106.6(5) . . ? N1 C5 C6 122.6(6) . . ? C4 C5 C6 130.8(5) . . ? C7 C6 C11 117.6(6) . . ? C7 C6 C5 119.6(6) . . ? C11 C6 C5 122.8(5) . . ? C6 C7 C8 121.8(6) . . ? C6 C7 H7A 119.1 . . ? C8 C7 H7A 119.1 . . ? C9 C8 C7 119.8(5) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? O1 C9 C8 125.2(6) . . ? O1 C9 C10 116.2(6) . . ? C8 C9 C10 118.7(6) . . ? C11 C10 C9 120.5(6) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C6 121.5(6) . . ? C10 C11 H11A 119.3 . . ? C6 C11 H11A 119.3 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 120.2(6) . . ? C14 C13 S1 120.8(5) . . ? C18 C13 S1 118.9(5) . . ? C13 C14 C15 120.3(7) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C16 C15 C14 121.6(7) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C15 C16 C17 117.9(7) . . ? C15 C16 C19 124.6(8) . . ? C17 C16 C19 117.4(8) . . ? C18 C17 C16 118.9(7) . . ? C18 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? C13 C18 C17 121.0(6) . . ? C13 C18 H18A 119.5 . . ? C17 C18 H18A 119.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C21 108.0(5) . . ? N4 C20 H20A 126.0 . . ? C21 C20 H20A 126.0 . . ? C20 C21 C22 107.2(5) . . ? C20 C21 H21A 126.4 . . ? C22 C21 H21A 126.4 . . ? N3 C22 C21 106.5(5) . . ? N3 C22 C23 123.3(6) . . ? C21 C22 C23 130.1(6) . . ? C28 C23 C24 116.8(6) . . ? C28 C23 C22 122.8(5) . . ? C24 C23 C22 120.4(6) . . ? C25 C24 C23 121.4(6) . . ? C25 C24 H24A 119.3 . . ? C23 C24 H24A 119.3 . . ? C26 C25 C24 120.1(6) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? O5 C26 C25 125.0(6) . . ? O5 C26 C27 115.4(6) . . ? C25 C26 C27 119.6(6) . . ? C28 C27 C26 120.5(6) . . ? C28 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? C27 C28 C23 121.5(6) . . ? C27 C28 H28A 119.2 . . ? C23 C28 H28A 119.2 . . ? O5 C29 H29A 109.5 . . ? O5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C48 C47 C52 119.4(7) . . ? C48 C47 S3 121.2(6) . . ? C52 C47 S3 119.4(6) . . ? C47 C48 C49 120.2(7) . . ? C47 C48 H48A 119.9 . . ? C49 C48 H48A 119.9 . . ? C50 C49 C48 122.8(8) . . ? C50 C49 H49A 118.6 . . ? C48 C49 H49A 118.6 . . ? C49 C50 C51 116.1(8) . . ? C49 C50 C53 123.3(9) . . ? C51 C50 C53 120.7(8) . . ? C52 C51 C50 121.5(8) . . ? C52 C51 H51A 119.2 . . ? C50 C51 H51A 119.2 . . ? C47 C52 C51 120.0(7) . . ? C47 C52 H52A 120.0 . . ? C51 C52 H52A 120.0 . . ? C50 C53 H53A 109.5 . . ? C50 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C50 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? N6 C37 C38 108.2(6) . . ? N6 C37 H37A 125.9 . . ? C38 C37 H37A 125.9 . . ? C37 C38 C39 105.9(5) . . ? C37 C38 H38A 127.0 . . ? C39 C38 H38A 127.0 . . ? N5 C39 C38 107.3(6) . . ? N5 C39 C40 122.0(6) . . ? C38 C39 C40 130.7(6) . . ? C45 C40 C41 116.2(6) . . ? C45 C40 C39 122.1(6) . . ? C41 C40 C39 121.7(6) . . ? C42 C41 C40 120.8(6) . . ? C42 C41 H41A 119.6 . . ? C40 C41 H41A 119.6 . . ? C41 C42 C43 120.9(6) . . ? C41 C42 H42A 119.5 . . ? C43 C42 H42A 119.5 . . ? C44 C43 O9 125.5(6) . . ? C44 C43 C42 119.1(6) . . ? O9 C43 C42 115.4(6) . . ? C45 C44 C43 119.3(6) . . ? C45 C44 H44A 120.3 . . ? C43 C44 H44A 120.3 . . ? C44 C45 C40 123.6(6) . . ? C44 C45 H45A 118.2 . . ? C40 C45 H45A 118.2 . . ? O9 C46 H46A 109.5 . . ? O9 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O9 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C31 C30 C35 117.5(6) . . ? C31 C30 S2 120.5(5) . . ? C35 C30 S2 122.0(5) . . ? C30 C31 C32 121.6(6) . . ? C30 C31 H31A 119.2 . . ? C32 C31 H31A 119.2 . . ? C33 C32 C31 121.1(7) . . ? C33 C32 H32A 119.5 . . ? C31 C32 H32A 119.5 . . ? C32 C33 C34 117.2(7) . . ? C32 C33 C36 121.6(7) . . ? C34 C33 C36 121.1(7) . . ? C35 C34 C33 121.3(6) . . ? C35 C34 H34A 119.4 . . ? C33 C34 H34A 119.4 . . ? C30 C35 C34 121.2(6) . . ? C30 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N2 N1 C5 109.3(5) . . ? N2 N1 H1 115.0 . . ? C5 N1 H1 134.8 . . ? C3 N2 N1 109.1(5) . . ? C3 N2 H2 119.4 . . ? N1 N2 H2 131.4 . . ? C22 N3 N4 111.1(5) . . ? C22 N3 H3 136.0 . . ? N4 N3 H3 112.9 . . ? N3 N4 C20 107.2(5) . . ? N3 N4 H4 124.1 . . ? C20 N4 H4 128.0 . . ? N6 N5 C39 108.8(5) . . ? N6 N5 H5 121.0 . . ? C39 N5 H5 130.2 . . ? N5 N6 C37 109.8(5) . . ? N5 N6 H6 117.7 . . ? C37 N6 H6 132.4 . . ? C9 O1 C12 117.9(5) . . ? C26 O5 C29 116.5(5) . . ? C43 O9 C46 117.2(5) . . ? O3 S1 O2 113.6(2) . . ? O3 S1 O4 113.4(2) . . ? O2 S1 O4 111.2(2) . . ? O3 S1 C13 105.5(2) . . ? O2 S1 C13 105.8(3) . . ? O4 S1 C13 106.5(3) . . ? O11 S3 O12 114.3(3) . . ? O11 S3 O10 113.5(3) . . ? O12 S3 O10 110.5(2) . . ? O11 S3 C47 106.2(3) . . ? O12 S3 C47 106.0(3) . . ? O10 S3 C47 105.6(3) . . ? O7 S2 O6 113.8(2) . . ? O7 S2 O8 113.2(2) . . ? O6 S2 O8 111.7(2) . . ? O7 S2 C30 106.3(2) . . ? O6 S2 C30 105.2(3) . . ? O8 S2 C30 105.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C3 C4 C5 0.5(7) . . . . ? C3 C4 C5 N1 -1.1(6) . . . . ? C3 C4 C5 C6 178.3(6) . . . . ? N1 C5 C6 C7 -172.5(5) . . . . ? C4 C5 C6 C7 8.1(9) . . . . ? N1 C5 C6 C11 6.8(9) . . . . ? C4 C5 C6 C11 -172.6(6) . . . . ? C11 C6 C7 C8 1.1(9) . . . . ? C5 C6 C7 C8 -179.6(5) . . . . ? C6 C7 C8 C9 -2.2(9) . . . . ? C7 C8 C9 O1 -178.8(5) . . . . ? C7 C8 C9 C10 1.3(9) . . . . ? O1 C9 C10 C11 -179.2(5) . . . . ? C8 C9 C10 C11 0.7(9) . . . . ? C9 C10 C11 C6 -1.8(10) . . . . ? C7 C6 C11 C10 0.9(9) . . . . ? C5 C6 C11 C10 -178.3(5) . . . . ? C18 C13 C14 C15 -0.6(9) . . . . ? S1 C13 C14 C15 176.6(5) . . . . ? C13 C14 C15 C16 2.4(10) . . . . ? C14 C15 C16 C17 -2.4(11) . . . . ? C14 C15 C16 C19 -178.6(6) . . . . ? C15 C16 C17 C18 0.7(11) . . . . ? C19 C16 C17 C18 177.1(6) . . . . ? C14 C13 C18 C17 -1.2(10) . . . . ? S1 C13 C18 C17 -178.4(5) . . . . ? C16 C17 C18 C13 1.1(10) . . . . ? N4 C20 C21 C22 -0.7(7) . . . . ? C20 C21 C22 N3 0.5(7) . . . . ? C20 C21 C22 C23 179.0(5) . . . . ? N3 C22 C23 C28 -5.6(9) . . . . ? C21 C22 C23 C28 176.1(6) . . . . ? N3 C22 C23 C24 174.9(5) . . . . ? C21 C22 C23 C24 -3.3(9) . . . . ? C28 C23 C24 C25 0.3(8) . . . . ? C22 C23 C24 C25 179.8(5) . . . . ? C23 C24 C25 C26 0.2(9) . . . . ? C24 C25 C26 O5 179.6(5) . . . . ? C24 C25 C26 C27 -0.2(10) . . . . ? O5 C26 C27 C28 179.9(5) . . . . ? C25 C26 C27 C28 -0.2(10) . . . . ? C26 C27 C28 C23 0.8(9) . . . . ? C24 C23 C28 C27 -0.8(9) . . . . ? C22 C23 C28 C27 179.7(5) . . . . ? C52 C47 C48 C49 0.8(10) . . . . ? S3 C47 C48 C49 -178.2(5) . . . . ? C47 C48 C49 C50 -1.0(11) . . . . ? C48 C49 C50 C51 1.8(11) . . . . ? C48 C49 C50 C53 -177.6(6) . . . . ? C49 C50 C51 C52 -2.4(12) . . . . ? C53 C50 C51 C52 177.0(7) . . . . ? C48 C47 C52 C51 -1.4(10) . . . . ? S3 C47 C52 C51 177.6(5) . . . . ? C50 C51 C52 C47 2.2(12) . . . . ? N6 C37 C38 C39 2.2(7) . . . . ? C37 C38 C39 N5 -2.0(7) . . . . ? C37 C38 C39 C40 179.9(6) . . . . ? N5 C39 C40 C45 3.7(9) . . . . ? C38 C39 C40 C45 -178.4(6) . . . . ? N5 C39 C40 C41 -176.0(5) . . . . ? C38 C39 C40 C41 1.9(10) . . . . ? C45 C40 C41 C42 1.2(9) . . . . ? C39 C40 C41 C42 -179.1(6) . . . . ? C40 C41 C42 C43 -1.8(10) . . . . ? C41 C42 C43 C44 1.8(10) . . . . ? C41 C42 C43 O9 -178.5(5) . . . . ? O9 C43 C44 C45 179.0(6) . . . . ? C42 C43 C44 C45 -1.4(9) . . . . ? C43 C44 C45 C40 0.9(10) . . . . ? C41 C40 C45 C44 -0.8(9) . . . . ? C39 C40 C45 C44 179.4(6) . . . . ? C35 C30 C31 C32 -1.3(10) . . . . ? S2 C30 C31 C32 177.1(5) . . . . ? C30 C31 C32 C33 3.1(11) . . . . ? C31 C32 C33 C34 -2.3(11) . . . . ? C31 C32 C33 C36 177.0(6) . . . . ? C32 C33 C34 C35 -0.1(10) . . . . ? C36 C33 C34 C35 -179.4(6) . . . . ? C31 C30 C35 C34 -1.1(9) . . . . ? S2 C30 C35 C34 -179.5(4) . . . . ? C33 C34 C35 C30 1.9(10) . . . . ? C4 C5 N1 N2 1.4(6) . . . . ? C6 C5 N1 N2 -178.1(5) . . . . ? C4 C3 N2 N1 0.3(6) . . . . ? C5 N1 N2 C3 -1.1(6) . . . . ? C21 C22 N3 N4 -0.2(6) . . . . ? C23 C22 N3 N4 -178.8(5) . . . . ? C22 N3 N4 C20 -0.3(6) . . . . ? C21 C20 N4 N3 0.6(6) . . . . ? C38 C39 N5 N6 1.1(7) . . . . ? C40 C39 N5 N6 179.4(5) . . . . ? C39 N5 N6 C37 0.3(7) . . . . ? C38 C37 N6 N5 -1.6(7) . . . . ? C8 C9 O1 C12 -2.6(9) . . . . ? C10 C9 O1 C12 177.3(5) . . . . ? C25 C26 O5 C29 3.6(9) . . . . ? C27 C26 O5 C29 -176.5(5) . . . . ? C44 C43 O9 C46 -0.9(9) . . . . ? C42 C43 O9 C46 179.4(5) . . . . ? C14 C13 S1 O3 -99.8(5) . . . . ? C18 C13 S1 O3 77.4(5) . . . . ? C14 C13 S1 O2 21.0(5) . . . . ? C18 C13 S1 O2 -161.8(5) . . . . ? C14 C13 S1 O4 139.4(5) . . . . ? C18 C13 S1 O4 -43.4(5) . . . . ? C48 C47 S3 O11 107.5(5) . . . . ? C52 C47 S3 O11 -71.5(6) . . . . ? C48 C47 S3 O12 -14.4(6) . . . . ? C52 C47 S3 O12 166.7(5) . . . . ? C48 C47 S3 O10 -131.7(5) . . . . ? C52 C47 S3 O10 49.4(5) . . . . ? C31 C30 S2 O7 -92.4(5) . . . . ? C35 C30 S2 O7 85.9(5) . . . . ? C31 C30 S2 O6 146.5(5) . . . . ? C35 C30 S2 O6 -35.2(5) . . . . ? C31 C30 S2 O8 28.1(6) . . . . ? C35 C30 S2 O8 -153.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.98 1.82 2.752(6) 156.7 . N2 H2 O6 0.97 1.90 2.790(6) 151.0 . N3 H3 O8 1.09 1.67 2.754(5) 170.3 . N4 H4 O2 1.00 1.93 2.767(6) 140.1 . N5 H5 O12 1.04 1.73 2.757(6) 165.3 . N6 H6 O10 0.94 1.91 2.741(6) 146.4 2_566 C38 H38A O11 0.93 2.35 3.240(7) 160.3 1_655 C21 H21A O7 0.93 2.37 3.275(6) 163.3 1_455 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.403 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.058 #=======================================================================END