# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jason A. C. Clyburne' _publ_contact_author_email jason.clyburne@smu.ca _publ_contact_author_phone '01 902 420-5827' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Ionic Liquids and Acid Gas Capture: Water and Oxygen as Confounding Factors ; loop_ _publ_author_name _publ_author_address 'Luke J. Murphy' ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Alex M. McPherson' ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Katherine N. Robertson' ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Jason A. C. Clyburne' ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; _journal_coeditor_code ? _journal_date_accepted ? _journal_date_from_coeditor ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? # Attachment '- clyburne_combined_revised.cif' data_[DETAH3][SO3][Cl] _database_code_depnum_ccdc_archive 'CCDC 842509' #TrackingRef '- clyburne_combined_revised.cif' _audit_creation_date 2011-08-12 _audit_creation_method 'SHELXL-97 ' _audit_update_record ? # _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H16 N3, O3 S, Cl' _chemical_formula_sum 'C4 H16 Cl N3 O3 S' _chemical_formula_weight 221.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/m _symmetry_space_group_name_Hall '-P 2yb' _symmetry_Int_Tables_number 11 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 4.936(3) _cell_length_b 9.726(5) _cell_length_c 10.030(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.299(5) _cell_angle_gamma 90.00 _cell_volume 479.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3631 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 28.52 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9216 _exptl_absorpt_correction_T_max 0.9541 _exptl_absorpt_process_details 'SADABS; Bruker 2009' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5790 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.84 _reflns_number_total 1260 _reflns_number_gt 1101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0412P)^2^+0.3989P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1260 _refine_ls_number_parameters 91 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.89745(11) 0.7500 0.00066(5) 0.01005(15) Uani 1 2 d S . . O1 O 0.5888(4) 0.7289(4) -0.0215(2) 0.0128(10) Uani 0.50 1 d PD . . O2 O 0.9312(4) 0.9072(2) 0.0059(2) 0.0136(5) Uani 0.50 1 d P . . O3 O 0.9599(4) 0.7054(2) 0.1487(2) 0.0136(5) Uani 0.50 1 d P . . Cl1 Cl 0.03726(11) 0.7500 0.59371(5) 0.01544(16) Uani 1 2 d S . . N1 N 0.4768(4) 0.7500 0.2679(2) 0.0176(4) Uani 1 2 d SD . . H1 H 0.629(7) 0.7500 0.211(3) 0.032(9) Uiso 1 2 d S . . H2 H 0.317(4) 0.7500 0.219(3) 0.027(8) Uiso 1 2 d SD . . N2 N 0.6650(3) 0.44785(18) 0.18800(16) 0.0210(4) Uani 1 1 d D . . H3 H 0.790(4) 0.404(2) 0.243(2) 0.031(6) Uiso 1 1 d D . . H4 H 0.761(5) 0.513(2) 0.150(2) 0.046(8) Uiso 1 1 d D . . H5 H 0.607(5) 0.389(2) 0.126(2) 0.043(8) Uiso 1 1 d D . . C1 C 0.4988(4) 0.6212(2) 0.34895(17) 0.0215(4) Uani 1 1 d . . . H1A H 0.3707 0.6255 0.4192 0.026 Uiso 1 1 calc R . . H1B H 0.6854 0.6130 0.3937 0.026 Uiso 1 1 calc R . . C2 C 0.4347(3) 0.4959(2) 0.26154(17) 0.0207(4) Uani 1 1 d . . . H2A H 0.3784 0.4199 0.3186 0.025 Uiso 1 1 calc R . . H2B H 0.2787 0.5178 0.1958 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0107(3) 0.0103(3) 0.0092(3) 0.000 0.00101(18) 0.000 O1 0.0116(9) 0.012(3) 0.0147(9) 0.0008(10) -0.0010(7) -0.0019(9) O2 0.0144(11) 0.0108(11) 0.0156(11) 0.0013(9) 0.0011(9) -0.0014(8) O3 0.0145(10) 0.0149(11) 0.0111(10) 0.0028(8) -0.0002(8) 0.0012(8) Cl1 0.0137(3) 0.0197(3) 0.0127(3) 0.000 -0.00020(19) 0.000 N1 0.0149(10) 0.0282(12) 0.0096(9) 0.000 0.0014(7) 0.000 N2 0.0139(7) 0.0307(9) 0.0180(7) 0.0099(7) -0.0001(6) -0.0010(6) C1 0.0247(9) 0.0296(10) 0.0102(7) 0.0016(7) 0.0010(6) -0.0114(8) C2 0.0159(8) 0.0315(10) 0.0149(8) -0.0021(7) 0.0022(6) -0.0090(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 S1 O1 1.533(2) . ? S1 O1 1.533(2) 4_575 ? S1 O2 1.539(2) . ? S1 O2 1.539(2) 4_575 ? S1 O3 1.550(2) 4_575 ? S1 O3 1.550(2) . ? O1 O1 0.411(8) 4_575 ? O2 O3 1.798(3) 4_575 ? O3 O3 0.868(4) 4_575 ? O3 O2 1.798(3) 4_575 ? N1 C1 1.492(2) . ? N1 C1 1.492(2) 4_575 ? N1 H1 0.98(4) . ? N1 H2 0.890(11) . ? N2 C2 1.487(2) . ? N2 H3 0.899(13) . ? N2 H4 0.900(14) . ? N2 H5 0.879(14) . ? C1 C2 1.517(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? 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 O1 S1 O2 103.96(18) . . ? O1 S1 O2 103.96(18) 4_575 4_575 ? O1 S1 O3 106.46(12) . 4_575 ? O1 S1 O3 102.03(13) 4_575 4_575 ? O2 S1 O3 103.55(12) 4_575 4_575 ? O1 S1 O3 102.03(13) . . ? O1 S1 O3 106.46(12) 4_575 . ? O2 S1 O3 103.55(12) . . ? C1 N1 C1 114.22(19) . 4_575 ? C1 N1 H1 107.2(10) . . ? C1 N1 H1 107.2(10) 4_575 . ? C1 N1 H2 108.5(10) . . ? C1 N1 H2 108.5(10) 4_575 . ? H1 N1 H2 111(3) . . ? C2 N2 H3 110.9(15) . . ? C2 N2 H4 116.3(17) . . ? H3 N2 H4 104(2) . . ? C2 N2 H5 110.3(18) . . ? H3 N2 H5 107(2) . . ? H4 N2 H5 108(2) . . ? N1 C1 C2 111.02(15) . . ? N1 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? N1 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? N2 C2 C1 114.28(15) . . ? N2 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N2 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? 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 O2 S1 O1 O1 1.07(9) . . . 4_575 ? O2 S1 O1 O1 178.96(9) 4_575 . . 4_575 ? O3 S1 O1 O1 75.26(10) 4_575 . . 4_575 ? O3 S1 O1 O1 108.51(9) . . . 4_575 ? O1 S1 O2 O3 102.94(13) . . . 4_575 ? O1 S1 O2 O3 103.22(12) 4_575 . . 4_575 ? O2 S1 O2 O3 -67.4(8) 4_575 . . 4_575 ? O3 S1 O2 O3 -3.37(5) . . . 4_575 ? O1 S1 O3 O3 -101.82(16) . . . 4_575 ? O1 S1 O3 O3 -86.60(16) 4_575 . . 4_575 ? O2 S1 O3 O3 5.94(9) . . . 4_575 ? O2 S1 O3 O3 173.90(9) 4_575 . . 4_575 ? O1 S1 O3 O2 84.29(18) . . . 4_575 ? O1 S1 O3 O2 99.51(18) 4_575 . . 4_575 ? O2 S1 O3 O2 -167.95(18) . . . 4_575 ? O3 S1 O3 O2 -173.90(9) 4_575 . . 4_575 ? C1 N1 C1 C2 171.91(12) 4_575 . . . ? N1 C1 C2 N2 81.0(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 O3 0.98(4) 1.85(3) 2.798(3) 160(2) . N1 H1 O3 0.98(4) 1.85(3) 2.798(3) 160(2) 4_575 N1 H2 O3 0.890(11) 1.888(12) 2.751(3) 162.9(19) 1_455 N1 H2 O3 0.890(11) 1.888(12) 2.751(3) 162.9(19) 4_475 N2 H3 Cl1 0.899(13) 2.319(16) 3.1722(19) 158(2) 3_666 N2 H4 O2 0.900(14) 1.901(17) 2.738(3) 154(2) 4_575 N2 H4 O3 0.900(14) 2.111(18) 2.942(3) 153(2) . N2 H5 O1 0.879(14) 1.773(16) 2.632(4) 165(3) 3_665 N2 H5 O1 0.879(14) 2.062(16) 2.917(4) 164(2) 2_645 C1 H1A Cl1 0.99 2.79 3.718(2) 156.7 . C1 H1B Cl1 0.99 2.86 3.668(2) 139.5 1_655 C2 H2A Cl1 0.99 2.84 3.726(2) 149.8 3_566 C2 H2B O2 0.99 2.44 3.211(3) 134.7 2_645 C2 H2B O3 0.99 2.43 3.231(3) 137.9 1_455 C2 H2B O2 0.99 2.55 3.530(3) 171.1 4_475 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.732 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.072 #============================================================================== data_[DETAH2][SO3]H2O _database_code_depnum_ccdc_archive 'CCDC 842510' #TrackingRef '- clyburne_combined_revised.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H15 N3, O3 S, H2 O' _chemical_formula_sum 'C4 H17 N3 O4 S' _chemical_formula_weight 203.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.746(3) _cell_length_b 8.502(4) _cell_length_c 9.273(4) _cell_angle_alpha 110.552(4) _cell_angle_beta 95.519(5) _cell_angle_gamma 94.516(5) _cell_volume 492.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 3476 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.54 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9395 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details 'SADABS; Bruker 2009' _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5954 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.86 _reflns_number_total 2358 _reflns_number_gt 1988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0479P)^2^+0.0583P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2358 _refine_ls_number_parameters 153 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.32352(5) 0.68885(5) 0.30144(4) 0.02962(13) Uani 1 1 d . . . O1 O 0.15064(15) 0.54992(14) 0.27041(14) 0.0366(3) Uani 1 1 d . . . O2 O 0.34523(17) 0.69928(14) 0.14303(12) 0.0362(3) Uani 1 1 d . . . O3 O 0.50812(17) 0.61241(18) 0.34091(15) 0.0456(3) Uani 1 1 d . . . C1 C -0.0993(2) 1.2043(2) 0.2991(2) 0.0399(4) Uani 1 1 d . . . H1A H -0.2206 1.2016 0.3468 0.048 Uiso 1 1 calc R . . H1B H -0.1025 1.2918 0.2546 0.048 Uiso 1 1 calc R . . C2 C 0.0802(2) 1.2517(2) 0.42440(19) 0.0375(4) Uani 1 1 d . . . H2A H 0.0579 1.3505 0.5109 0.045 Uiso 1 1 calc R . . H2B H 0.0922 1.1595 0.4621 0.045 Uiso 1 1 calc R . . C3 C -0.1400(2) 0.89642(19) 0.22066(18) 0.0318(3) Uani 1 1 d . . . H3A H -0.2533 0.9111 0.2792 0.038 Uiso 1 1 calc R . . H3B H -0.0241 0.8879 0.2868 0.038 Uiso 1 1 calc R . . C4 C -0.1856(2) 0.73689(19) 0.07824(18) 0.0325(3) Uani 1 1 d . . . H4A H -0.3059 0.7436 0.0154 0.039 Uiso 1 1 calc R . . H4B H -0.0758 0.7268 0.0166 0.039 Uiso 1 1 calc R . . N1 N -0.0999(2) 1.04148(17) 0.17392(16) 0.0331(3) Uani 1 1 d D . . H1 H 0.014(3) 1.028(4) 0.136(4) 0.024(8) Uiso 0.50 1 d PD . . H2 H -0.196(4) 1.039(4) 0.106(3) 0.025(8) Uiso 0.50 1 d PD . . N2 N 0.2695(2) 1.2886(2) 0.36822(18) 0.0368(3) Uani 1 1 d D . . H3 H 0.259(3) 1.375(2) 0.334(2) 0.052(6) Uiso 1 1 d D . . H4 H 0.300(3) 1.197(2) 0.293(2) 0.055(6) Uiso 1 1 d D . . H5 H 0.360(3) 1.320(3) 0.449(2) 0.054(6) Uiso 1 1 d D . . N3 N -0.2151(2) 0.58507(17) 0.12112(16) 0.0308(3) Uani 1 1 d D . . H6 H -0.308(3) 0.590(3) 0.185(2) 0.048(5) Uiso 1 1 d D . . H7 H -0.254(3) 0.496(2) 0.0375(19) 0.042(5) Uiso 1 1 d D . . H8 H -0.099(3) 0.572(3) 0.170(2) 0.052(6) Uiso 1 1 d D . . O4 O 0.3753(2) 1.00525(19) 0.1171(2) 0.0553(4) Uani 1 1 d D . . H9 H 0.370(4) 0.917(3) 0.131(3) 0.085(9) Uiso 1 1 d D . . H10 H 0.475(5) 1.012(6) 0.078(5) 0.064(15) Uiso 0.50 1 d PD . . H11 H 0.264(5) 1.018(8) 0.083(7) 0.11(2) Uiso 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0291(2) 0.0292(2) 0.0275(2) 0.00777(15) 0.00206(14) -0.00036(14) O1 0.0265(5) 0.0407(6) 0.0473(7) 0.0232(5) 0.0022(5) -0.0010(5) O2 0.0447(7) 0.0326(6) 0.0325(6) 0.0159(5) 0.0007(5) -0.0032(5) O3 0.0285(6) 0.0682(8) 0.0451(7) 0.0302(6) -0.0057(5) 0.0024(5) C1 0.0329(8) 0.0319(8) 0.0529(11) 0.0144(8) 0.0015(7) 0.0021(6) C2 0.0440(9) 0.0371(9) 0.0279(8) 0.0088(7) 0.0052(7) -0.0024(7) C3 0.0328(8) 0.0327(8) 0.0306(8) 0.0134(6) 0.0015(6) 0.0017(6) C4 0.0340(8) 0.0326(8) 0.0317(8) 0.0135(6) 0.0019(6) 0.0030(6) N1 0.0317(7) 0.0343(7) 0.0346(7) 0.0166(6) -0.0005(6) -0.0013(6) N2 0.0344(7) 0.0411(8) 0.0360(8) 0.0189(7) -0.0040(6) -0.0018(6) N3 0.0284(7) 0.0301(7) 0.0317(7) 0.0099(6) 0.0004(5) 0.0016(5) O4 0.0408(8) 0.0424(8) 0.0928(12) 0.0385(8) 0.0022(8) 0.0053(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.5211(13) . ? S1 O1 1.5224(12) . ? S1 O2 1.5224(13) . ? C1 N1 1.460(2) . ? C1 C2 1.517(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.477(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.458(2) . ? C3 C4 1.509(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.483(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N1 H1 0.876(18) . ? N1 H2 0.852(18) . ? N2 H3 0.903(15) . ? N2 H4 0.896(15) . ? N2 H5 0.866(16) . ? N3 H6 0.895(15) . ? N3 H7 0.873(15) . ? N3 H8 0.899(15) . ? O4 H9 0.805(17) . ? O4 H10 0.804(19) . ? O4 H11 0.82(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O1 104.31(7) . . ? O3 S1 O2 104.76(7) . . ? O1 S1 O2 104.80(6) . . ? N1 C1 C2 114.41(14) . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? N2 C2 C1 112.59(14) . . ? N2 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N2 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? N1 C3 C4 109.58(13) . . ? N1 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? N1 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N3 C4 C3 111.27(13) . . ? N3 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N3 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C3 N1 C1 113.62(14) . . ? C3 N1 H1 104(2) . . ? C1 N1 H1 114(2) . . ? C3 N1 H2 108(2) . . ? C1 N1 H2 104(2) . . ? H1 N1 H2 112(3) . . ? C2 N2 H3 109.1(13) . . ? C2 N2 H4 111.4(14) . . ? H3 N2 H4 110.8(19) . . ? C2 N2 H5 105.5(14) . . ? H3 N2 H5 109(2) . . ? H4 N2 H5 111(2) . . ? C4 N3 H6 113.8(13) . . ? C4 N3 H7 109.6(12) . . ? H6 N3 H7 106.7(18) . . ? C4 N3 H8 109.5(13) . . ? H6 N3 H8 107.0(18) . . ? H7 N3 H8 110.1(18) . . ? H9 O4 H10 106(4) . . ? H9 O4 H11 110(5) . . ? H10 O4 H11 124(6) . . ? 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 N1 C1 C2 N2 68.54(19) . . . . ? N1 C3 C4 N3 176.53(12) . . . . ? C4 C3 N1 C1 166.83(13) . . . . ? C2 C1 N1 C3 71.26(18) . . . . ? 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 0.876(18) 2.48(2) 3.319(3) 161(3) . N1 H2 O4 0.852(18) 2.19(2) 3.009(2) 162(3) 2_575 N2 H3 O1 0.903(15) 1.947(16) 2.821(2) 162.4(18) 1_565 N2 H3 S1 0.903(15) 2.793(16) 3.664(2) 162.5(17) 1_565 N2 H4 O4 0.896(15) 2.002(16) 2.896(2) 175.6(19) . N2 H5 O3 0.866(16) 1.930(17) 2.768(2) 163(2) 2_676 N3 H6 O3 0.895(15) 1.965(16) 2.857(2) 174.4(19) 1_455 N3 H6 S1 0.895(15) 2.873(16) 3.6957(19) 153.5(16) 1_455 N3 H7 O2 0.873(15) 1.903(15) 2.7764(19) 178.6(18) 2_565 N3 H8 O1 0.899(15) 1.902(16) 2.801(2) 177.8(19) . O4 H9 O2 0.805(17) 1.886(17) 2.689(2) 174(3) . O4 H10 O4 0.804(19) 2.12(3) 2.853(4) 152(5) 2_675 O4 H11 N1 0.82(2) 2.67(5) 3.319(3) 137(6) . O4 H11 N1 0.82(2) 2.39(5) 3.009(2) 133(6) 2_575 _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.226 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.048 #============================================================================== # End of CIF #==============================================================================