#Electronic Supplementary Material for CrystEngComm #This Journal is (c) The Royal Society of Chemistry 2007 data_General _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _audit_creation_date 2007-01-24 _audit_creation_method 'by CrystalStructure 3.6.0' # SUBMISSION DETAILS _publ_contact_author_name 'Dr. Peddy Vishweshwar' _publ_contact_author_address ; Department of Analytical Research Discovery Research Dr. Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; _publ_contact_author_email vishweshwarp@drreddys.com _publ_contact_author_fax 91-040-23045440 _publ_contact_author_phone 91-9866827284 #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Solid-State Structural Studies of Saccharin Salts with Some Heterocyclic Bases ; _publ_section_title_footnote ; DRL Publication number:-635 ; loop_ _publ_author_name _publ_author_address P.Sudhakar ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; 'Vijay Kumar' ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; P.Vishweshwar ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; 'J.Moses Babu' ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; K.Vyas ; Department of Analytical Research Discovery Research Dr.Reddy's Laboratories Ltd. Miyapur Hyderabad 500049 Andhrapradesh INDIA ; #============================================================================== data_salt_1 _database_code_depnum_ccdc_archive 'CCDC 666292' #============================================================================== # CHEMICAL DATA _chemical_name_common ; 1,2-bis(4-pyridinium)ethane saccharinate (1:2) ; _exptl_crystal_preparation Methanol _chemical_formula_sum 'C26 H22 N4 O6 S2' _chemical_formula_moiety 'C12 H14 N2, 2(C7 H4 N O3 S)' _chemical_formula_weight 550.60 _chemical_melting_point 494 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.5770(8) _cell_length_b 11.0722(13) _cell_length_c 15.260(2) _cell_angle_alpha 90 _cell_angle_beta 90.809(11) _cell_angle_gamma 90 _cell_volume 1280.1(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6067 _cell_measurement_theta_min 1.3 _cell_measurement_theta_max 24.9 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.33 _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572.00 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.918 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 11932 _diffrn_reflns_av_R_equivalents 0.074 _diffrn_reflns_theta_max 24.93 _diffrn_measured_fraction_theta_max 0.9886 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 0.9886 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.5 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2200 _reflns_number_gt 982 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1400 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1870 _refine_ls_number_parameters 186 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 115921.0000 163195.0000 49653.9000 ; _refine_ls_shift/su_max 0.0050 _refine_diff_density_max 0.35 _refine_diff_density_min -0.45 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics 'X-seed 2.0' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani 0.9265(3) 0.7824(3) 0.7811(2) 1.000 0.0427(10) . . C8 C Uani 0.9275(4) 0.6655(3) 0.7614(2) 1.000 0.0444(12) . . C9 C Uani 0.9190(4) 0.5789(3) 0.8269(2) 1.000 0.0423(12) . . C10 C Uani 0.9127(4) 0.6146(3) 0.9141(2) 1.000 0.0384(10) . . C11 C Uani 0.9101(5) 0.7364(3) 0.9322(2) 1.000 0.0527(12) . . C12 C Uani 0.9160(5) 0.8202(3) 0.8647(2) 1.000 0.0530(14) . . C13 C Uani 0.9069(4) 0.5211(3) 0.9863(2) 1.000 0.0433(12) . . S1 S Uani 0.42984(9) 0.70517(7) 0.69652(5) 1.000 0.0383(3) . . O1 O Uani 0.2639(3) 0.7066(3) 0.6492(2) 1.000 0.0581(8) . . O2 O Uani 0.5721(3) 0.7675(2) 0.6532(2) 1.000 0.0520(10) . . O3 O Uani 0.5301(3) 0.4553(2) 0.84690(10) 1.000 0.0481(9) . . N1 N Uani 0.4862(4) 0.5692(2) 0.7233(2) 1.000 0.0430(10) . . C1 C Uani 0.4930(4) 0.5535(3) 0.8105(2) 1.000 0.0350(12) . . C2 C Uani 0.4500(3) 0.6660(3) 0.8615(2) 1.000 0.0327(8) . . C3 C Uani 0.4489(4) 0.6834(3) 0.9523(2) 1.000 0.0423(12) . . C4 C Uani 0.4071(5) 0.7974(4) 0.9834(2) 1.000 0.0577(16) . . C5 C Uani 0.3620(5) 0.8918(4) 0.9262(3) 1.000 0.0583(12) . . C6 C Uani 0.3616(4) 0.8748(3) 0.8356(2) 1.000 0.0460(12) . . C7 C Uani 0.4074(4) 0.7613(3) 0.8053(2) 1.000 0.0334(10) . . H8 H Uiso 0.93110 0.64120 0.70170 1.000 0.0530 calc R H9 H Uiso 0.92170 0.49530 0.81280 1.000 0.0510 calc R H11 H Uiso 0.90340 0.76290 0.99120 1.000 0.0630 calc R H12 H Uiso 0.91450 0.90420 0.87730 1.000 0.0640 calc R H21 H Uiso 0.925(5) 0.851(4) 0.731(3) 1.000 0.076(13) d . H131 H Uiso 0.85070 0.55490 1.03590 1.000 0.0520 calc R H132 H Uiso 0.84190 0.45280 0.96640 1.000 0.0520 calc R H3 H Uiso 0.48040 0.61930 0.99090 1.000 0.0510 calc R H4 H Uiso 0.40510 0.81090 1.04490 1.000 0.0690 calc R H5 H Uiso 0.33270 0.96880 0.94920 1.000 0.0700 calc R H6 H Uiso 0.33080 0.93790 0.79600 1.000 0.0550 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 N2 0.049(2) 0.040(2) 0.0390(10) 0.0130(12) -0.0065(11) 0.0003(12) C8 0.054(2) 0.045(2) 0.034(2) 0.0020(10) -0.0010(10) 0.002(2) C9 0.050(2) 0.034(2) 0.043(2) 0.0070(10) 0.0060(10) 0.0010(10) C10 0.0380(10) 0.041(2) 0.036(2) 0.0090(10) -0.0029(12) -0.0064(13) C11 0.081(2) 0.043(2) 0.034(2) 0.003(2) 0.000(2) -0.007(2) C12 0.085(3) 0.033(2) 0.041(2) 0.005(2) 0.001(2) -0.009(2) C13 0.049(2) 0.045(2) 0.036(2) 0.0170(10) 0.0010(10) -0.0080(10) S1 0.0492(5) 0.0374(5) 0.0283(4) 0.0016(3) -0.0006(3) -0.0009(3) O1 0.0540(10) 0.076(2) 0.0440(10) 0.0053(13) -0.0139(11) 0.0001(10) O2 0.064(2) 0.049(2) 0.0434(13) 0.0095(11) 0.0133(11) -0.0065(11) O3 0.073(2) 0.0283(12) 0.0431(12) 0.0018(10) 0.0004(11) 0.0030(10) N1 0.065(2) 0.032(2) 0.0319(13) -0.0022(11) -0.0019(11) 0.0008(12) C1 0.042(2) 0.028(2) 0.035(2) 0.0012(12) -0.0018(12) -0.0045(12) C2 0.0340(10) 0.031(2) 0.0330(10) 0.0012(12) -0.0023(11) -0.0037(11) C3 0.050(2) 0.045(2) 0.032(2) 0.0012(13) 0.0007(13) -0.0026(13) C4 0.075(3) 0.061(3) 0.037(2) -0.014(2) 0.002(2) 0.002(2) C5 0.072(2) 0.049(2) 0.054(2) -0.015(2) 0.005(2) 0.010(2) C6 0.052(2) 0.037(2) 0.049(2) -0.004(2) -0.002(2) 0.0060(10) C7 0.0360(10) 0.032(2) 0.032(2) 0.0002(12) -0.0011(12) -0.0024(11) #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.441(3) . . no S1 O2 1.448(3) . . no S1 N1 1.616(3) . . no S1 C7 1.783(4) . . no O3 C1 1.251(4) . . no N2 C8 1.329(5) . . no N2 C12 1.346(5) . . no N2 H21 1.08(5) . . no N1 C1 1.342(5) . . no C8 C9 1.387(5) . . no C9 C10 1.390(5) . . no C10 C13 1.513(5) . . no C10 C11 1.377(5) . . no C11 C12 1.388(5) . . no C13 C13 1.539(5) . 3_767 no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H132 0.9500 . . no C13 H131 0.9500 . . no C1 C2 1.507(5) . . no C2 C3 1.399(5) . . no C2 C7 1.395(5) . . no C3 C4 1.387(6) . . no C4 C5 1.401(6) . . no C5 C6 1.395(6) . . no C6 C7 1.385(5) . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C7 96.76(15) . . . no O1 S1 C7 111.64(16) . . . no O1 S1 O2 114.58(17) . . . no O1 S1 N1 111.26(17) . . . no O2 S1 N1 111.34(15) . . . no O2 S1 C7 109.90(16) . . . no C8 N2 C12 121.2(3) . . . no C8 N2 H21 122(2) . . . no C12 N2 H21 117(2) . . . no S1 N1 C1 112.2(2) . . . no N2 C8 C9 120.7(3) . . . no C8 C9 C10 119.7(3) . . . no C11 C10 C13 121.6(3) . . . no C9 C10 C11 118.1(3) . . . no C9 C10 C13 120.3(3) . . . no C10 C11 C12 120.4(3) . . . no N2 C12 C11 119.9(3) . . . no C10 C13 C13 111.7(3) . . 3_767 no N2 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C10 C9 H9 120.00 . . . no C8 C9 H9 121.00 . . . no C12 C11 H11 120.00 . . . no C10 C11 H11 120.00 . . . no N2 C12 H12 120.00 . . . no C11 C12 H12 120.00 . . . no C10 C13 H131 109.00 . . . no C10 C13 H132 109.00 . . . no H131 C13 H132 109.00 . . . no C13 C13 H131 109.00 3_767 . . no C13 C13 H132 108.00 3_767 . . no O3 C1 N1 123.9(3) . . . no O3 C1 C2 122.5(3) . . . no N1 C1 C2 113.5(3) . . . no C1 C2 C3 129.0(3) . . . no C1 C2 C7 111.0(3) . . . no C3 C2 C7 120.0(3) . . . no C2 C3 C4 118.0(3) . . . no C3 C4 C5 121.4(3) . . . no C4 C5 C6 120.9(4) . . . no C5 C6 C7 117.1(3) . . . no S1 C7 C2 106.5(2) . . . no S1 C7 C6 130.9(2) . . . no C2 C7 C6 122.6(3) . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 122.00 . . . no C3 C4 H4 119.00 . . . no C5 C4 H4 119.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 119.00 . . . no C5 C6 H6 122.00 . . . no C7 C6 H6 121.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C7 C6 -64.3(4) . . . . no O2 S1 C7 C2 -114.7(2) . . . . no O2 S1 C7 C6 64.0(3) . . . . no N1 S1 C7 C2 0.9(2) . . . . no N1 S1 C7 C6 179.7(3) . . . . no O2 S1 N1 C1 114.6(3) . . . . no C7 S1 N1 C1 0.1(3) . . . . no O1 S1 C7 C2 117.0(2) . . . . no O1 S1 N1 C1 -116.3(3) . . . . no C8 N2 C12 C11 1.5(5) . . . . no C12 N2 C8 C9 -0.5(4) . . . . no S1 N1 C1 C2 -1.0(3) . . . . no S1 N1 C1 O3 178.5(3) . . . . no N2 C8 C9 C10 -1.2(5) . . . . no C8 C9 C10 C11 1.8(5) . . . . no C8 C9 C10 C13 -178.8(3) . . . . no C9 C10 C13 C13 86.0(4) . . . 3_767 no C9 C10 C11 C12 -0.8(5) . . . . no C11 C10 C13 C13 -94.7(4) . . . 3_767 no C13 C10 C11 C12 179.8(3) . . . . no C10 C11 C12 N2 -0.8(5) . . . . no C10 C13 C13 C10 -180.0(3) . . 3_767 3_767 no O3 C1 C2 C3 2.3(5) . . . . no O3 C1 C2 C7 -177.8(3) . . . . no N1 C1 C2 C3 -178.1(3) . . . . no N1 C1 C2 C7 1.7(4) . . . . no C1 C2 C3 C4 178.9(3) . . . . no C7 C2 C3 C4 -0.9(4) . . . . no C1 C2 C7 S1 -1.5(3) . . . . no C1 C2 C7 C6 179.6(3) . . . . no C3 C2 C7 S1 178.4(2) . . . . no C3 C2 C7 C6 -0.5(4) . . . . no C2 C3 C4 C5 1.9(5) . . . . no C3 C4 C5 C6 -1.5(6) . . . . no C4 C5 C6 C7 0.0(5) . . . . no C5 C6 C7 S1 -177.6(3) . . . . no C5 C6 C7 C2 1.0(5) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 H11 3.1600 . 4_464 no O1 C8 3.124(6) . 1_455 no O2 C8 3.336(6) . . no O3 N2 2.758(5) . 2_646 no O3 C9 3.267(6) . . no O1 H8 2.7500 . 1_455 no O1 H11 2.6700 . 4_464 no O2 H9 2.5800 . 2_656 no O2 H132 2.8300 . 2_656 no O2 H11 2.7900 . 4_464 no O3 H21 1.70(4) . 2_646 no O3 H3 2.6100 . 3_667 no O3 H3 2.8800 . . no N1 C12 3.159(6) . 2_646 no N1 N2 3.245(6) . 2_646 no N2 N1 3.245(6) . 2_656 no N2 O3 2.758(5) . 2_656 no N2 C1 3.370(6) . 2_656 no N1 H6 2.8200 . 2_546 no N1 H12 2.5100 . 2_646 no N1 H21 2.60(4) . 2_646 no C1 N2 3.370(6) . 2_646 no C1 C9 3.246(6) . . no C1 C10 3.596(6) . . no C3 C11 3.561(7) . . no C5 C12 3.583(7) . 1_455 no C6 C12 3.465(7) . 1_455 no C8 O2 3.336(6) . . no C8 O1 3.124(6) . 1_655 no C9 C1 3.246(6) . . no C9 O3 3.267(6) . . no C10 C1 3.596(6) . . no C11 C3 3.561(7) . . no C12 N1 3.159(6) . 2_656 no C12 C6 3.465(7) . 1_655 no C12 C5 3.583(7) . 1_655 no C1 H21 2.41(4) . 2_646 no C3 H132 2.9600 . 3_667 no C9 H131 3.0900 . 3_767 no H3 O3 2.8800 . . no H3 O3 2.6100 . 3_667 no H4 H8 2.4600 . 4_465 no H6 N1 2.8200 . 2_556 no H8 O1 2.7500 . 1_655 no H8 H4 2.4600 . 4_564 no H9 O2 2.5800 . 2_646 no H9 H132 2.4700 . . no H11 O2 2.7900 . 4_565 no H11 H131 2.4400 . . no H11 S1 3.1600 . 4_565 no H11 O1 2.6700 . 4_565 no H12 N1 2.5100 . 2_656 no H21 N1 2.60(4) . 2_656 no H21 O3 1.70(4) . 2_656 no H21 C1 2.41(4) . 2_656 no H131 C9 3.0900 . 3_767 no H131 H11 2.4400 . . no H132 C3 2.9600 . 3_667 no H132 H9 2.4700 . . no H132 O2 2.8300 . 2_646 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H21 O3 1.08(5) 1.70(4) 2.758(5) 168(3) 2_656 yes C3 H3 O3 0.9500 2.6100 3.429(6) 144.00 3_667 yes C9 H9 O2 0.9500 2.5800 3.462(6) 155.00 2_646 yes C11 H11 O1 0.9500 2.6700 3.563(6) 157.00 4_565 yes C12 H12 N1 0.9500 2.5100 3.159(6) 126.00 2_656 yes #===END # Attachment 'Salt_2.cif' #============================================================================== data_salt_2 _database_code_depnum_ccdc_archive 'CCDC 666293' #============================================================================== # CHEMICAL DATA _chemical_name_common ; 1,2-bis(4-pyridinium)ethylene saccharinate (1:2) ; _exptl_crystal_preparation Methanol _chemical_formula_sum 'C26 H20 N4 O6 S2 ' _chemical_formula_moiety 'C12 H12 N2, 2(C7 H4 N O3 S)' _chemical_formula_weight 548.59 _chemical_melting_point 507 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z #------------------------------------------------------------------------------ _cell_length_a 13.161(2) _cell_length_b 5.251(2) _cell_length_c 18.590(12) _cell_angle_alpha 90 _cell_angle_beta 106.828(3) _cell_angle_gamma 90 _cell_volume 1229.7(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4870 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 29.0 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568.00 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.948 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 14736 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_theta_max 29.50 _diffrn_measured_fraction_theta_max 0.8825 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.9974 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 1.2 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3039 _reflns_number_gt 1454 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.0930 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1842 _refine_ls_number_parameters 182 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 5342.9800 7406.6400 2203.0300 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.68 _refine_diff_density_min -0.66 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics 'X-seed 2.0' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani 0.4787(2) -0.1564(6) 0.1621(2) 1.000 0.0451(12) . . C8 C Uani 0.5765(3) -0.0692(8) 0.1729(2) 1.000 0.0499(14) . . C9 C Uani 0.5961(3) 0.1276(8) 0.1301(2) 1.000 0.0465(14) . . C10 C Uani 0.5145(3) 0.2367(8) 0.0740(2) 1.000 0.0369(12) . . C11 C Uani 0.4125(3) 0.1338(8) 0.0638(2) 1.000 0.0467(14) . . C12 C Uani 0.3977(3) -0.0587(8) 0.1082(2) 1.000 0.0499(14) . . C13 C Uani 0.5356(3) 0.4455(8) 0.0285(2) 1.000 0.0417(12) . . S1 S Uani 0.64686(7) 0.2311(2) 0.37025(6) 1.000 0.0489(3) . . O1 O Uani 0.7212(2) 0.0730(7) 0.3466(2) 1.000 0.0707(14) . . O2 O Uani 0.6918(2) 0.3710(6) 0.4391(2) 1.000 0.0636(12) . . O3 O Uani 0.4132(2) 0.4825(6) 0.23130(10) 1.000 0.0503(12) . . N1 N Uani 0.5838(2) 0.4191(7) 0.3023(2) 1.000 0.0448(12) . . C1 C Uani 0.4807(3) 0.3684(8) 0.2832(2) 1.000 0.0410(12) . . C2 C Uani 0.4485(3) 0.1601(7) 0.3263(2) 1.000 0.0371(12) . . C3 C Uani 0.3478(3) 0.0698(8) 0.3209(2) 1.000 0.0466(14) . . C4 C Uani 0.3382(3) -0.1285(9) 0.3678(2) 1.000 0.0540(16) . . C5 C Uani 0.4273(3) -0.2321(9) 0.4179(2) 1.000 0.0562(16) . . C6 C Uani 0.5278(3) -0.1426(8) 0.4235(2) 1.000 0.0485(12) . . C7 C Uani 0.5360(3) 0.0556(8) 0.3779(2) 1.000 0.0396(12) . . H2 H Uiso 0.46590 -0.28870 0.19330 1.000 0.0550 calc R H8 H Uiso 0.63370 -0.14370 0.21030 1.000 0.0580 calc R H9 H Uiso 0.66640 0.19010 0.13920 1.000 0.0540 calc R H11 H Uiso 0.35370 0.20010 0.02590 1.000 0.0560 calc R H12 H Uiso 0.32840 -0.12640 0.10040 1.000 0.0600 calc R H13 H Uiso 0.60580 0.51100 0.04050 1.000 0.0490 calc R H3 H Uiso 0.28690 0.14220 0.28630 1.000 0.0550 calc R H4 H Uiso 0.26990 -0.19360 0.36540 1.000 0.0650 calc R H5 H Uiso 0.41900 -0.36860 0.44930 1.000 0.0690 calc R H6 H Uiso 0.58880 -0.21580 0.45780 1.000 0.0560 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 N2 0.057(2) 0.037(2) 0.044(2) 0.008(2) 0.019(2) 0.003(2) C8 0.048(2) 0.053(3) 0.043(2) 0.010(2) 0.004(2) 0.007(2) C9 0.041(2) 0.053(3) 0.041(2) 0.005(2) 0.005(2) -0.001(2) C10 0.042(2) 0.036(2) 0.031(2) 0.001(2) 0.0080(10) -0.001(2) C11 0.043(2) 0.051(3) 0.045(2) 0.008(2) 0.011(2) 0.006(2) C12 0.043(2) 0.053(3) 0.053(2) 0.003(2) 0.013(2) -0.003(2) C13 0.041(2) 0.044(2) 0.038(2) 0.002(2) 0.008(2) 0.001(2) S1 0.0309(4) 0.0553(6) 0.0572(6) 0.0022(6) 0.0077(4) 0.0017(5) O1 0.039(2) 0.075(2) 0.101(3) 0.000(2) 0.025(2) 0.016(2) O2 0.045(2) 0.074(2) 0.057(2) -0.005(2) -0.0088(13) -0.006(2) O3 0.046(2) 0.053(2) 0.048(2) 0.0180(10) 0.0073(12) 0.0020(10) N1 0.035(2) 0.048(2) 0.051(2) 0.007(2) 0.0120(10) -0.002(2) C1 0.037(2) 0.043(2) 0.042(2) 0.002(2) 0.010(2) -0.001(2) C2 0.035(2) 0.038(2) 0.038(2) -0.004(2) 0.010(2) 0.000(2) C3 0.036(2) 0.051(3) 0.051(2) 0.006(2) 0.010(2) 0.002(2) C4 0.049(2) 0.056(3) 0.058(3) 0.002(2) 0.017(2) -0.016(2) C5 0.075(3) 0.045(3) 0.051(2) 0.007(2) 0.022(2) -0.010(2) C6 0.053(2) 0.041(2) 0.045(2) 0.008(2) 0.004(2) 0.005(2) C7 0.036(2) 0.039(2) 0.043(2) -0.003(2) 0.010(2) 0.004(2) #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.446(4) . . no S1 N1 1.629(4) . . no S1 C7 1.766(5) . . no S1 O1 1.445(4) . . no O3 C1 1.258(5) . . no N2 C8 1.326(5) . . no N2 C12 1.336(5) . . no N2 H2 0.9500 . . no N1 C1 1.326(5) . . no C8 C9 1.373(6) . . no C9 C10 1.386(6) . . no C10 C13 1.460(6) . . no C10 C11 1.408(6) . . no C11 C12 1.354(6) . . no C13 C13 1.324(6) . 3_665 no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13 0.9500 . . no C1 C2 1.488(6) . . no C2 C3 1.384(6) . . no C2 C7 1.381(6) . . no C3 C4 1.387(6) . . no C4 C5 1.381(6) . . no C5 C6 1.379(6) . . no C6 C7 1.366(6) . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 110.49(19) . . . no O1 S1 C7 111.9(2) . . . no O2 S1 N1 111.39(19) . . . no O2 S1 C7 109.25(18) . . . no N1 S1 C7 97.55(17) . . . no O1 S1 O2 114.95(19) . . . no C8 N2 C12 120.7(3) . . . no C12 N2 H2 120.00 . . . no C8 N2 H2 120.00 . . . no S1 N1 C1 109.8(3) . . . no N2 C8 C9 120.6(4) . . . no C8 C9 C10 120.8(4) . . . no C11 C10 C13 123.0(3) . . . no C9 C10 C11 116.3(4) . . . no C9 C10 C13 120.7(4) . . . no C10 C11 C12 120.3(4) . . . no N2 C12 C11 121.3(4) . . . no C10 C13 C13 125.4(4) . . 3_665 no C9 C8 H8 120.00 . . . no N2 C8 H8 120.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C10 C11 H11 120.00 . . . no C12 C11 H11 120.00 . . . no N2 C12 H12 120.00 . . . no C11 C12 H12 119.00 . . . no C10 C13 H13 118.00 . . . no C13 C13 H13 117.00 3_665 . . no O3 C1 N1 123.4(4) . . . no O3 C1 C2 121.0(4) . . . no N1 C1 C2 115.6(3) . . . no C1 C2 C3 129.0(4) . . . no C1 C2 C7 110.9(4) . . . no C3 C2 C7 120.2(4) . . . no C2 C3 C4 118.1(4) . . . no C3 C4 C5 120.4(4) . . . no C4 C5 C6 121.7(4) . . . no C5 C6 C7 117.3(4) . . . no S1 C7 C2 106.2(3) . . . no S1 C7 C6 131.5(3) . . . no C2 C7 C6 122.3(4) . . . no C2 C3 H3 121.00 . . . no C4 C3 H3 121.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C4 C5 H5 119.00 . . . no C6 C5 H5 119.00 . . . no C5 C6 H6 121.00 . . . no C7 C6 H6 121.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C7 C6 63.1(4) . . . . no O2 S1 C7 C2 113.8(3) . . . . no O2 S1 C7 C6 -65.3(4) . . . . no N1 S1 C7 C2 -2.0(3) . . . . no N1 S1 C7 C6 178.9(4) . . . . no O2 S1 N1 C1 -112.9(3) . . . . no C7 S1 N1 C1 1.3(3) . . . . no O1 S1 C7 C2 -117.7(3) . . . . no O1 S1 N1 C1 118.1(3) . . . . no C8 N2 C12 C11 -0.9(6) . . . . no C12 N2 C8 C9 1.6(6) . . . . no S1 N1 C1 C2 -0.2(4) . . . . no S1 N1 C1 O3 -178.8(3) . . . . no N2 C8 C9 C10 -1.0(6) . . . . no C8 C9 C10 C11 -0.3(6) . . . . no C8 C9 C10 C13 -179.9(4) . . . . no C9 C10 C13 C13 176.7(4) . . . 3_665 no C9 C10 C11 C12 1.0(6) . . . . no C11 C10 C13 C13 -2.9(6) . . . 3_665 no C13 C10 C11 C12 -179.5(4) . . . . no C10 C11 C12 N2 -0.4(6) . . . . no C10 C13 C13 C10 -180.0(4) . . 3_665 3_665 no O3 C1 C2 C3 -3.4(6) . . . . no O3 C1 C2 C7 177.3(4) . . . . no N1 C1 C2 C3 177.9(4) . . . . no N1 C1 C2 C7 -1.4(5) . . . . no C1 C2 C3 C4 -180.0(4) . . . . no C7 C2 C3 C4 -0.8(6) . . . . no C1 C2 C7 S1 2.1(4) . . . . no C1 C2 C7 C6 -178.7(4) . . . . no C3 C2 C7 S1 -177.3(3) . . . . no C3 C2 C7 C6 2.0(6) . . . . no C2 C3 C4 C5 -0.4(6) . . . . no C3 C4 C5 C6 0.4(6) . . . . no C4 C5 C6 C7 0.7(6) . . . . no C5 C6 C7 S1 177.1(3) . . . . no C5 C6 C7 C2 -1.9(6) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2 O3 0.9500 1.6500 2.576(6) 165.00 1_545 yes N2 H2 N1 0.9500 2.6500 3.404(7) 136.00 1_545 yes C9 H9 O1 0.9500 2.4600 3.292(7) 146.00 2_655 yes C11 H11 O2 0.9500 2.3000 3.148(7) 148.00 4_454 yes C13 H13 O1 0.9500 2.6300 3.432(7) 142.00 2_655 yes #============================================================================== data_salt_3 _database_code_depnum_ccdc_archive 'CCDC 666294' #============================================================================== # CHEMICAL DATA _exptl_crystal_preparation 'Methanol and water' _chemical_formula_sum 'C18 H20 N4 O6 S2 ' _chemical_formula_moiety 'C4 H12 N2, 2(C7 H4 N O3 S)' _chemical_formula_weight 452.50 _chemical_melting_point 524 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.1261(10) _cell_length_b 9.3971(8) _cell_length_c 9.6281(10) _cell_angle_alpha 90.0000 _cell_angle_beta 99.489(4) _cell_angle_gamma 90.0000 _cell_volume 992.88(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5600 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472.00 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.939 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 10969 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_theta_max 27.44 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.980 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 0.1 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2228 _reflns_number_gt 1893 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0530 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2200 _refine_ls_number_parameters 153 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 9708.1600 13375.9000 3748.9300 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.29 _refine_diff_density_min -0.36 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 554(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani 1.04605(13) 0.36466(16) 0.46595(15) 1.000 0.0320(4) . . C8 C Uani 1.04626(15) 0.40662(18) 0.61493(17) 1.000 0.0326(5) . . C9 C Uani 1.05586(14) 0.56587(17) 0.63026(17) 1.000 0.0335(5) . . S1 S Uani 0.81544(3) 0.48204(4) 0.95433(4) 1.000 0.0298(1) . . O1 O Uani 0.89426(11) 0.36368(13) 0.99923(14) 1.000 0.0438(4) . . O2 O Uani 0.82229(10) 0.59550(13) 1.05569(13) 1.000 0.0394(3) . . O3 O Uani 0.72450(10) 0.55155(14) 0.58052(12) 1.000 0.0431(4) . . N1 N Uani 0.83296(11) 0.54026(16) 0.80265(14) 1.000 0.0376(4) . . C1 C Uani 0.73163(13) 0.52143(18) 0.70731(16) 1.000 0.0324(4) . . C2 C Uani 0.62841(13) 0.45596(17) 0.76733(17) 1.000 0.0308(4) . . C3 C Uani 0.51090(14) 0.4264(2) 0.70150(18) 1.000 0.0395(5) . . C4 C Uani 0.43382(15) 0.3574(2) 0.7795(2) 1.000 0.0442(6) . . C5 C Uani 0.47215(15) 0.3199(2) 0.9171(2) 1.000 0.0432(5) . . C6 C Uani 0.58933(15) 0.35121(18) 0.98521(18) 1.000 0.0375(5) . . C7 C Uani 0.66405(13) 0.42121(17) 0.90659(17) 1.000 0.0302(4) . . H21 H Uiso 1.1237(17) 0.394(2) 0.4436(19) 1.000 0.050(5) d . H22 H Uiso 1.0364(17) 0.273(2) 0.459(2) 1.000 0.052(6) d . H81 H Uiso 1.11290 0.36260 0.67360 1.000 0.0390 calc R H82 H Uiso 0.97210 0.37610 0.64220 1.000 0.0390 calc R H91 H Uiso 1.05270 0.59230 0.72480 1.000 0.0400 calc R H92 H Uiso 1.13120 0.59600 0.60580 1.000 0.0400 calc R H3 H Uiso 0.48420 0.45280 0.60620 1.000 0.0470 calc R H4 H Uiso 0.35280 0.33610 0.73620 1.000 0.0530 calc R H5 H Uiso 0.41800 0.27040 0.96680 1.000 0.0530 calc R H6 H Uiso 0.61660 0.32680 1.08100 1.000 0.0460 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 N2 0.0345(7) 0.0264(7) 0.0369(7) 0.0003(5) 0.0112(5) 0.0026(5) C8 0.0333(8) 0.0341(8) 0.0309(8) 0.0057(6) 0.0065(6) 0.0035(6) C9 0.0343(8) 0.0356(8) 0.0306(8) -0.0023(6) 0.0055(6) -0.0013(6) S1 0.0229(2) 0.0305(2) 0.0355(2) -0.0010(2) 0.0033(1) 0.0001(2) O1 0.0352(6) 0.0362(6) 0.0578(8) 0.0026(5) 0.0012(5) 0.0095(5) O2 0.0361(6) 0.0386(6) 0.0434(6) -0.0108(5) 0.0060(4) -0.0054(5) O3 0.0367(6) 0.0585(8) 0.0354(6) 0.0083(5) 0.0101(4) 0.0009(5) N1 0.0264(6) 0.0478(8) 0.0389(7) 0.0049(6) 0.0062(5) -0.0037(6) C1 0.0259(6) 0.0357(8) 0.0363(8) 0.0019(7) 0.0069(6) 0.0024(6) C2 0.0251(6) 0.0321(8) 0.0360(8) -0.0020(6) 0.0073(5) 0.0008(6) C3 0.0311(8) 0.0490(10) 0.0370(9) -0.0005(7) 0.0014(6) -0.0030(7) C4 0.0265(8) 0.0512(11) 0.0539(11) -0.0053(8) 0.0036(7) -0.0082(7) C5 0.0329(8) 0.0421(9) 0.0572(11) 0.0027(8) 0.0152(8) -0.0079(7) C6 0.0363(8) 0.0378(9) 0.0395(9) 0.0024(7) 0.0093(7) -0.0037(7) C7 0.0242(7) 0.0276(7) 0.0382(8) -0.0016(6) 0.0038(6) 0.0004(5) #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4389(13) . . yes S1 N1 1.6012(14) . . yes S1 O1 1.4381(13) . . yes S1 C7 1.7663(15) . . yes O3 C1 1.2429(19) . . yes N2 C9 1.491(2) . 3_766 yes N2 C8 1.487(2) . . yes N2 H21 0.964(19) . . no N2 H22 0.869(19) . . no N1 C1 1.343(2) . . yes C8 C9 1.506(2) . . no C8 H81 0.9500 . . no C8 H82 0.9500 . . no C9 H92 0.9500 . . no C9 H91 0.9500 . . no C1 C2 1.500(2) . . no C2 C3 1.384(2) . . no C2 C7 1.373(2) . . no C3 C4 1.390(2) . . no C4 C5 1.369(3) . . no C5 C6 1.391(2) . . no C6 C7 1.380(2) . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 C7 110.97(7) . . . yes N1 S1 C7 97.32(7) . . . yes O1 S1 C7 109.64(7) . . . yes O1 S1 O2 114.06(7) . . . yes O1 S1 N1 112.24(8) . . . yes O2 S1 N1 111.38(8) . . . yes C8 N2 C9 111.30(13) . . 3_766 yes C9 N2 H22 108.3(13) 3_766 . . no C8 N2 H21 106.3(11) . . . no C8 N2 H22 108.5(13) . . . no H21 N2 H22 111.7(17) . . . no C9 N2 H21 110.7(11) 3_766 . . no S1 N1 C1 111.33(11) . . . yes N2 C8 C9 110.29(13) . . . yes N2 C9 C8 109.87(13) 3_766 . . yes C9 C8 H81 110.00 . . . no N2 C8 H81 110.00 . . . no N2 C8 H82 109.00 . . . no C9 C8 H82 109.00 . . . no H81 C8 H82 109.00 . . . no C8 C9 H91 110.00 . . . no C8 C9 H92 109.00 . . . no H91 C9 H92 109.00 . . . no N2 C9 H91 110.00 3_766 . . no N2 C9 H92 109.00 3_766 . . no O3 C1 N1 123.49(14) . . . yes O3 C1 C2 122.88(14) . . . yes N1 C1 C2 113.61(13) . . . yes C1 C2 C3 129.15(15) . . . no C1 C2 C7 110.94(13) . . . no C3 C2 C7 119.89(15) . . . no C2 C3 C4 117.82(16) . . . no C3 C4 C5 121.42(16) . . . no C4 C5 C6 121.33(16) . . . no C5 C6 C7 116.41(16) . . . no S1 C7 C2 106.65(11) . . . yes S1 C7 C6 130.27(13) . . . yes C2 C7 C6 123.08(15) . . . no C2 C3 H3 121.00 . . . no C4 C3 H3 121.00 . . . no C3 C4 H4 119.00 . . . no C5 C4 H4 119.00 . . . no C4 C5 H5 119.00 . . . no C6 C5 H5 119.00 . . . no C5 C6 H6 122.00 . . . no C7 C6 H6 122.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C7 C6 60.11(18) . . . . no O2 S1 C7 C2 113.58(12) . . . . no O2 S1 C7 C6 -66.79(18) . . . . no O1 S1 N1 C1 115.23(12) . . . . no O2 S1 N1 C1 -115.49(12) . . . . no C7 S1 N1 C1 0.48(13) . . . . no O1 S1 C7 C2 -119.53(12) . . . . no N1 S1 C7 C2 -2.71(13) . . . . no N1 S1 C7 C6 176.92(16) . . . . no C9 N2 C8 C9 -57.79(17) 3_766 . . . no C8 N2 C9 C8 57.55(17) . . 3_766 3_766 no S1 N1 C1 O3 -176.36(14) . . . . no S1 N1 C1 C2 1.79(18) . . . . no N2 C8 C9 N2 56.95(17) . . . 3_766 no O3 C1 C2 C3 -4.3(3) . . . . no O3 C1 C2 C7 174.24(16) . . . . no N1 C1 C2 C3 177.51(17) . . . . no N1 C1 C2 C7 -3.9(2) . . . . no C1 C2 C3 C4 176.42(17) . . . . no C7 C2 C3 C4 -2.1(3) . . . . no C1 C2 C7 S1 3.89(16) . . . . no C1 C2 C7 C6 -175.78(15) . . . . no C3 C2 C7 S1 -177.38(13) . . . . no C3 C2 C7 C6 3.0(3) . . . . no C2 C3 C4 C5 0.2(3) . . . . no C3 C4 C5 C6 1.0(3) . . . . no C4 C5 C6 C7 -0.2(3) . . . . no C5 C6 C7 S1 178.64(14) . . . . no C5 C6 C7 C2 -1.8(2) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H21 O3 0.964(19) 1.816(19) 2.7774(19) 174.5(17) 3_766 yes N2 H21 N1 0.964(19) 2.572(18) 3.232(2) 125.8(14) 3_766 yes N2 H22 O2 0.869(19) 2.312(19) 2.9474(19) 130.0(16) 2_746 yes N2 H22 O1 0.869(19) 2.122(19) 2.782(2) 132.2(17) 4_554 yes C5 H5 O3 0.9500 2.5900 3.341(2) 136.00 2_646 yes # End of CIF #============================================================================== # Attachment 'Salt_4.cif' #============================================================================== data_Salt_4 _database_code_depnum_ccdc_archive 'CCDC 666295' #============================================================================== # CHEMICAL DATA _chemical_name_common ; 1,4-Dimethylpiperazinium saccharinate (1:2) ; _exptl_crystal_preparation Methanol _chemical_formula_sum 'C20 H24 N4 O6 S2 ' _chemical_formula_moiety 'C6 H16 N2, 2(C7 H4 N O3 S)' _chemical_formula_weight 480.55 _chemical_melting_point 489 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.973(2) _cell_length_b 15.413(3) _cell_length_c 9.293(2) _cell_angle_alpha 90 _cell_angle_beta 104.555(10) _cell_angle_gamma 90 _cell_volume 1105.4(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4805 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 29.1 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description chip _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504.00 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 13339 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_theta_max 29.53 _diffrn_measured_fraction_theta_max 0.8733 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.9912 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 1.2 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2686 _reflns_number_gt 1122 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1270 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1658 _refine_ls_number_parameters 161 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 3262.6700 4518.6500 1354.5000 ; _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.57 _refine_diff_density_min -0.49 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 50.9(50) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics 'X-seed 2.0' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N2 N Uani -0.0959(6) 0.4759(3) 0.1069(5) 1.000 0.0414(16) . . C8 C Uani -0.2595(8) 0.4636(5) 0.1565(7) 1.000 0.065(3) . . C9 C Uani -0.0771(7) 0.5683(4) 0.0662(6) 1.000 0.0453(19) . . C10 C Uani 0.0899(7) 0.5815(4) 0.0203(6) 1.000 0.0452(17) . . S1 S Uani 0.1332(2) 0.35366(10) 0.4641(2) 1.000 0.0444(4) . . O1 O Uani 0.0563(5) 0.4018(3) 0.5641(4) 1.000 0.0598(17) . . O2 O Uani 0.0430(6) 0.2757(3) 0.4043(5) 1.000 0.0725(17) . . O3 O Uani 0.4005(5) 0.4624(3) 0.2498(4) 1.000 0.0553(16) . . N1 N Uani 0.1688(6) 0.4135(3) 0.3320(5) 1.000 0.0453(17) . . C1 C Uani 0.3413(7) 0.4221(4) 0.3401(6) 1.000 0.0406(17) . . C2 C Uani 0.4523(6) 0.3755(3) 0.4722(5) 1.000 0.0367(17) . . C3 C Uani 0.6308(7) 0.3707(4) 0.5167(6) 1.000 0.0430(17) . . C4 C Uani 0.7042(7) 0.3190(4) 0.6402(6) 1.000 0.0486(19) . . C5 C Uani 0.6027(8) 0.2776(4) 0.7181(7) 1.000 0.056(2) . . C6 C Uani 0.4234(7) 0.2831(4) 0.6753(6) 1.000 0.052(2) . . C7 C Uani 0.3532(6) 0.3328(3) 0.5506(5) 1.000 0.0382(17) . . H2 H Uiso -0.007(8) 0.467(4) 0.190(7) 1.000 0.08(2) d . H81 H Uiso -0.24500 0.41820 0.22780 1.000 0.0800 calc R H82 H Uiso -0.35140 0.44930 0.07300 1.000 0.0800 calc R H83 H Uiso -0.28620 0.51600 0.19980 1.000 0.0800 calc R H91 H Uiso -0.07730 0.60440 0.14900 1.000 0.0540 calc R H92 H Uiso -0.17190 0.58340 -0.01440 1.000 0.0540 calc R H101 H Uiso 0.18500 0.56790 0.10170 1.000 0.0530 calc R H102 H Uiso 0.09780 0.64030 -0.00760 1.000 0.0530 calc R H3 H Uiso 0.70120 0.40120 0.46500 1.000 0.0510 calc R H4 H Uiso 0.82670 0.31350 0.67090 1.000 0.0550 calc R H5 H Uiso 0.65700 0.24330 0.80170 1.000 0.0650 calc R H6 H Uiso 0.35140 0.25520 0.72850 1.000 0.0610 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 N2 0.039(3) 0.050(3) 0.033(2) 0.008(2) 0.005(2) 0.001(2) C8 0.047(4) 0.099(6) 0.053(4) 0.005(4) 0.020(3) -0.010(4) C9 0.048(3) 0.050(4) 0.038(3) 0.000(3) 0.011(3) 0.007(3) C10 0.045(3) 0.047(3) 0.040(3) -0.002(3) 0.004(3) -0.006(3) S1 0.0411(8) 0.0500(8) 0.0393(7) 0.0064(7) 0.0050(6) -0.0032(7) O1 0.053(3) 0.079(3) 0.054(3) 0.007(2) 0.026(2) 0.009(2) O2 0.060(3) 0.074(3) 0.073(3) 0.000(3) -0.003(2) -0.022(3) O3 0.054(3) 0.074(3) 0.042(2) 0.016(2) 0.020(2) -0.001(2) N1 0.039(3) 0.057(3) 0.039(3) 0.010(2) 0.008(2) 0.002(2) C1 0.037(3) 0.046(3) 0.035(3) -0.007(3) 0.002(2) 0.003(3) C2 0.040(3) 0.037(3) 0.032(3) 0.000(2) 0.007(2) 0.001(2) C3 0.040(3) 0.048(3) 0.041(3) -0.009(3) 0.010(2) 0.005(3) C4 0.040(3) 0.056(4) 0.043(3) 0.000(3) -0.002(3) 0.004(3) C5 0.060(4) 0.053(4) 0.049(4) 0.020(3) 0.001(3) 0.002(3) C6 0.047(4) 0.057(4) 0.050(3) 0.011(3) 0.007(3) 0.003(3) C7 0.035(3) 0.043(3) 0.034(3) -0.002(2) 0.004(2) -0.004(2) #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.766(5) . . no S1 N1 1.617(5) . . no S1 O1 1.441(4) . . no S1 O2 1.438(5) . . no O3 C1 1.230(7) . . no N2 C10 1.487(7) . 3_565 no N2 C9 1.491(8) . . no N2 C8 1.501(8) . . no N2 H2 0.92(7) . . no N1 C1 1.365(8) . . no C9 C10 1.511(8) . . no C8 H83 0.9500 . . no C8 H81 0.9500 . . no C8 H82 0.9500 . . no C9 H91 0.9500 . . no C9 H92 0.9500 . . no C10 H102 0.9500 . . no C10 H101 0.9500 . . no C1 C2 1.503(7) . . no C2 C3 1.381(8) . . no C2 C7 1.370(7) . . no C3 C4 1.399(8) . . no C4 C5 1.371(9) . . no C5 C6 1.387(9) . . no C6 C7 1.385(7) . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C7 96.1(2) . . . no O1 S1 C7 109.6(2) . . . no O1 S1 O2 115.3(3) . . . no O1 S1 N1 112.4(3) . . . no O2 S1 N1 110.5(3) . . . no O2 S1 C7 111.5(3) . . . no C8 N2 C10 111.9(5) . . 3_565 no C8 N2 C9 110.4(5) . . . no C9 N2 C10 110.0(4) . . 3_565 no C10 N2 H2 114(4) 3_565 . . no C9 N2 H2 105(4) . . . no C8 N2 H2 106(4) . . . no S1 N1 C1 112.4(4) . . . no N2 C9 C10 110.6(5) . . . no N2 C10 C9 110.6(5) 3_565 . . no N2 C8 H81 110.00 . . . no H81 C8 H82 109.00 . . . no N2 C8 H82 109.00 . . . no N2 C8 H83 109.00 . . . no H81 C8 H83 109.00 . . . no H82 C8 H83 110.00 . . . no C10 C9 H91 109.00 . . . no N2 C9 H91 109.00 . . . no N2 C9 H92 109.00 . . . no C10 C9 H92 109.00 . . . no H91 C9 H92 109.00 . . . no C9 C10 H101 109.00 . . . no C9 C10 H102 109.00 . . . no H101 C10 H102 109.00 . . . no N2 C10 H101 109.00 3_565 . . no N2 C10 H102 109.00 3_565 . . no O3 C1 N1 124.5(5) . . . no O3 C1 C2 123.4(5) . . . no N1 C1 C2 112.1(5) . . . no C1 C2 C3 128.4(5) . . . no C1 C2 C7 111.3(4) . . . no C3 C2 C7 120.3(5) . . . no C2 C3 C4 117.6(5) . . . no C3 C4 C5 121.2(5) . . . no C4 C5 C6 121.5(6) . . . no C5 C6 C7 116.4(5) . . . no S1 C7 C2 108.1(3) . . . no S1 C7 C6 128.9(4) . . . no C2 C7 C6 123.0(5) . . . no C2 C3 H3 121.00 . . . no C4 C3 H3 121.00 . . . no C3 C4 H4 119.00 . . . no C5 C4 H4 120.00 . . . no C4 C5 H5 119.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 123.00 . . . no C7 C6 H6 121.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 S1 N1 C1 0.5(4) . . . . no O1 S1 C7 C2 -115.6(4) . . . . no O1 S1 C7 C6 64.3(5) . . . . no O2 S1 C7 C2 115.5(4) . . . . no O2 S1 C7 C6 -64.5(6) . . . . no O1 S1 N1 C1 114.6(4) . . . . no O2 S1 N1 C1 -115.2(4) . . . . no N1 S1 C7 C6 -179.3(5) . . . . no N1 S1 C7 C2 0.7(4) . . . . no C10 N2 C9 C10 -57.6(6) 3_565 . . . no C8 N2 C9 C10 178.4(4) . . . . no C8 N2 C10 C9 -179.3(5) . . 3_565 3_565 no C9 N2 C10 C9 57.6(6) . . 3_565 3_565 no S1 N1 C1 O3 177.8(5) . . . . no S1 N1 C1 C2 -1.5(6) . . . . no N2 C9 C10 N2 58.0(6) . . . 3_565 no O3 C1 C2 C3 1.4(9) . . . . no O3 C1 C2 C7 -177.3(5) . . . . no N1 C1 C2 C3 -179.2(5) . . . . no N1 C1 C2 C7 2.1(6) . . . . no C1 C2 C3 C4 -176.6(5) . . . . no C7 C2 C3 C4 2.0(8) . . . . no C1 C2 C7 S1 -1.6(5) . . . . no C1 C2 C7 C6 178.4(5) . . . . no C3 C2 C7 S1 179.6(4) . . . . no C3 C2 C7 C6 -0.4(8) . . . . no C2 C3 C4 C5 -2.8(9) . . . . no C3 C4 C5 C6 2.0(9) . . . . no C4 C5 C6 C7 -0.3(9) . . . . no C5 C6 C7 S1 179.6(4) . . . . no C5 C6 C7 C2 -0.5(8) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N2 H2 N1 0.92(7) 1.86(6) 2.745(7) 162(6) . yes C9 H92 O3 0.9500 2.5700 3.419(7) 149.00 3_565 yes C10 H101 O3 0.9500 2.5100 3.376(7) 151.00 . yes C4 H4 O1 0.9500 2.6600 3.318(7) 126.00 1_655 yes #===END # Attachment 'Salt_5.cif' #============================================================================== data_salt_5 _database_code_depnum_ccdc_archive 'CCDC 666296' #============================================================================== # CHEMICAL DATA _chemical_name_common ; 2,2'-dipyridiniumamine saccharinate (1:1) ; _exptl_crystal_preparation Methanol _chemical_formula_sum 'C17 H14 N4 O3 S ' _chemical_formula_moiety 'C10 H10 N3, C7 H4 N O3 S' _chemical_formula_weight 354.38 _chemical_melting_point 487 #============================================================================== # CRYSTAL DATA _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_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.635(2) _cell_length_b 13.385(4) _cell_length_c 14.149(3) _cell_angle_alpha 105.658(3) _cell_angle_beta 91.773(2) _cell_angle_gamma 110.444(2) _cell_volume 1630.3(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7273 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736.00 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_T_max 0.911 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 18611 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.9499 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.9788 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 7134 _reflns_number_gt 5053 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.0520 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 5095 _refine_ls_number_parameters 492 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 11927.4000 16505.4000 5060.7700 ; _refine_ls_shift/su_max 0.0080 _refine_diff_density_max 0.23 _refine_diff_density_min -0.33 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 293.1(20) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #=============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics 'X-seed 2.0' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N3 N Uani 0.3314(2) 0.02698(13) 0.13219(12) 1.000 0.0618(6) . . N4 N Uani 0.5339(2) -0.03000(10) 0.11371(12) 1.000 0.0602(6) . . N5 N Uani 0.6101(2) 0.16230(10) 0.13407(11) 1.000 0.0563(6) . . C15 C Uani 0.3842(2) -0.0536(2) 0.12523(13) 1.000 0.0547(7) . . C16 C Uani 0.2961(3) -0.1592(2) 0.1299(2) 1.000 0.0683(9) . . C17 C Uani 0.1495(3) -0.1799(2) 0.1415(2) 1.000 0.0793(10) . . C18 C Uani 0.0937(3) -0.0966(2) 0.1480(2) 1.000 0.0784(12) . . C19 C Uani 0.1875(3) 0.0045(2) 0.1433(2) 1.000 0.0695(8) . . C20 C Uani 0.6432(2) 0.0707(2) 0.12273(13) 1.000 0.0551(7) . . C21 C Uani 0.7926(3) 0.0816(2) 0.1196(2) 1.000 0.0718(10) . . C22 C Uani 0.8991(3) 0.1835(2) 0.1302(2) 1.000 0.0823(10) . . C23 C Uani 0.8612(3) 0.2764(2) 0.1433(2) 1.000 0.0753(10) . . C24 C Uani 0.7159(2) 0.2633(2) 0.1444(2) 1.000 0.0656(7) . . N6 N Uani 0.2839(2) -0.00135(12) 0.40164(11) 1.000 0.0498(5) . . N7 N Uani 0.5321(2) 0.05703(13) 0.37305(11) 1.000 0.0515(5) . . N8 N Uani 0.4436(2) -0.13035(13) 0.37179(11) 1.000 0.0506(5) . . C25 C Uani 0.4013(2) 0.07780(10) 0.38628(12) 1.000 0.0455(6) . . C26 C Uani 0.3987(2) 0.1802(2) 0.38200(10) 1.000 0.0593(7) . . C27 C Uani 0.2697(3) 0.1999(2) 0.3960(2) 1.000 0.0676(10) . . C28 C Uani 0.1472(2) 0.1185(2) 0.4132(2) 1.000 0.0650(7) . . C29 C Uani 0.1583(2) 0.0200(2) 0.41400(10) 1.000 0.0575(7) . . C30 C Uani 0.5529(2) -0.0403(2) 0.36253(11) 1.000 0.0455(6) . . C31 C Uani 0.6907(2) -0.0484(2) 0.34035(13) 1.000 0.0575(7) . . C32 C Uani 0.7075(2) -0.1478(2) 0.32870(10) 1.000 0.0652(9) . . C33 C Uani 0.5911(3) -0.2397(2) 0.3377(2) 1.000 0.0708(10) . . C34 C Uani 0.4614(2) -0.2284(2) 0.3598(2) 1.000 0.0648(6) . . S1 S Uani -0.02353(6) 0.32286(4) 0.63703(3) 1.000 0.0534(2) . . O1 O Uani -0.0693(2) 0.39474(13) 0.71423(10) 1.000 0.0764(6) . . O2 O Uani 0.0420(2) 0.25472(12) 0.67043(11) 1.000 0.0733(6) . . O3 O Uani -0.21220(10) 0.23193(11) 0.38369(10) 1.000 0.0608(4) . . N1 N Uani -0.1582(2) 0.24860(12) 0.54756(11) 1.000 0.0537(5) . . C1 C Uani 0.0239(2) 0.36485(13) 0.47464(12) 1.000 0.0401(5) . . C2 C Uani 0.0934(2) 0.40880(10) 0.40300(10) 1.000 0.0525(7) . . C3 C Uani 0.2372(2) 0.4855(2) 0.4284(2) 1.000 0.0662(9) . . C4 C Uani 0.3111(2) 0.5188(2) 0.5235(2) 1.000 0.0741(9) . . C5 C Uani 0.2424(2) 0.4767(2) 0.5964(2) 1.000 0.0650(7) . . C6 C Uani 0.0983(2) 0.39980(13) 0.56965(13) 1.000 0.0456(6) . . C7 C Uani -0.1270(2) 0.27656(13) 0.46423(13) 1.000 0.0438(5) . . S2 S Uani 0.36424(6) 0.35837(5) 0.16057(4) 1.000 0.0623(2) . . O4 O Uani 0.2460(2) 0.3082(2) 0.21217(11) 1.000 0.0940(8) . . O5 O Uani 0.4986(2) 0.4373(2) 0.22226(12) 1.000 0.1006(6) . . O6 O Uani 0.3710(2) 0.20290(10) -0.09253(11) 1.000 0.0953(8) . . N2 N Uani 0.3967(2) 0.26430(10) 0.07705(13) 1.000 0.0656(7) . . C8 C Uani 0.3044(2) 0.35810(10) -0.01357(13) 1.000 0.0493(6) . . C9 C Uani 0.2552(3) 0.3829(2) -0.0944(2) 1.000 0.0684(9) . . C10 C Uani 0.2012(3) 0.4681(2) -0.0768(2) 1.000 0.0734(10) . . C11 C Uani 0.1965(3) 0.5266(2) 0.0187(2) 1.000 0.0774(10) . . C12 C Uani 0.2453(2) 0.5033(2) 0.0994(2) 1.000 0.0703(6) . . C13 C Uani 0.2994(2) 0.41760(10) 0.08040(13) 1.000 0.0495(6) . . C14 C Uani 0.3599(2) 0.2669(2) -0.0134(2) 1.000 0.0599(6) . . H16 H Uiso 0.33720 -0.21510 0.12480 1.000 0.0820 calc R H17 H Uiso 0.08720 -0.25090 0.14590 1.000 0.0920 calc R H18 H Uiso -0.00830 -0.11020 0.15550 1.000 0.0930 calc R H19 H Uiso 0.14870 0.06160 0.14730 1.000 0.0860 calc R H21 H Uiso 0.81920 0.01800 0.11100 1.000 0.0920 calc R H22 H Uiso 1.00040 0.19030 0.12770 1.000 0.0990 calc R H23 H Uiso 0.93630 0.34780 0.15150 1.000 0.0880 calc R H24 H Uiso 0.68790 0.32610 0.15230 1.000 0.0770 calc R H41 H Uiso 0.576(3) -0.092(2) 0.098(2) 1.000 0.094(7) d . H51 H Uiso 0.507(2) 0.142(2) 0.1358(13) 1.000 0.059(6) d . H26 H Uiso 0.48440 0.23460 0.36950 1.000 0.0700 calc R H27 H Uiso 0.26430 0.26870 0.39350 1.000 0.0850 calc R H28 H Uiso 0.05730 0.13120 0.42470 1.000 0.0810 calc R H29 H Uiso 0.07260 -0.03700 0.42340 1.000 0.0700 calc R H31 H Uiso 0.77050 0.01440 0.33370 1.000 0.0670 calc R H32 H Uiso 0.80020 -0.15390 0.31380 1.000 0.0820 calc R H33 H Uiso 0.60380 -0.30880 0.32900 1.000 0.0950 calc R H34 H Uiso 0.38120 -0.29080 0.36680 1.000 0.0860 calc R H71 H Uiso 0.618(2) 0.116(2) 0.3720(10) 1.000 0.075(7) d . H81 H Uiso 0.367(2) -0.111(2) 0.392(2) 1.000 0.080(7) d . H2 H Uiso 0.04270 0.38600 0.33770 1.000 0.0640 calc R H3 H Uiso 0.28630 0.51660 0.37990 1.000 0.0780 calc R H4 H Uiso 0.41120 0.57140 0.53910 1.000 0.0800 calc R H5 H Uiso 0.29220 0.49950 0.66200 1.000 0.0710 calc R H9 H Uiso 0.25850 0.34230 -0.16010 1.000 0.0850 calc R H10 H Uiso 0.16640 0.48640 -0.13100 1.000 0.0900 calc R H11 H Uiso 0.15910 0.58510 0.02870 1.000 0.0940 calc R H12 H Uiso 0.24250 0.54410 0.16520 1.000 0.0820 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 N3 0.0705(12) 0.0595(10) 0.0613(10) 0.0163(8) 0.0102(8) 0.0324(9) N4 0.0738(12) 0.0567(11) 0.0563(10) 0.0096(8) 0.0057(8) 0.0373(10) N5 0.0576(11) 0.0574(10) 0.0566(10) 0.0141(8) 0.0031(8) 0.0272(9) C15 0.0673(13) 0.0536(11) 0.0414(10) 0.0077(8) 0.0056(9) 0.0255(10) C16 0.091(2) 0.0562(13) 0.0585(13) 0.0131(10) 0.0087(11) 0.0315(12) C17 0.089(2) 0.0640(10) 0.076(2) 0.0210(12) 0.0232(13) 0.0170(13) C18 0.074(2) 0.082(2) 0.076(2) 0.0211(13) 0.0239(12) 0.0260(10) C19 0.0670(10) 0.075(2) 0.0750(10) 0.0233(12) 0.0162(11) 0.0352(12) C20 0.0655(13) 0.0616(13) 0.0397(10) 0.0082(9) 0.0013(9) 0.0310(11) C21 0.075(2) 0.086(2) 0.0680(10) 0.0197(12) 0.0063(11) 0.0490(13) C22 0.0610(10) 0.104(2) 0.082(2) 0.0270(10) 0.0030(12) 0.0320(10) C23 0.0620(10) 0.082(2) 0.076(2) 0.0273(12) -0.0026(11) 0.0179(13) C24 0.0650(10) 0.0611(13) 0.0670(13) 0.0177(10) -0.0013(10) 0.0211(11) N6 0.0450(9) 0.0496(9) 0.0587(9) 0.0147(7) 0.0078(7) 0.0235(7) N7 0.0410(9) 0.0486(9) 0.0594(10) 0.0089(7) 0.0036(7) 0.0160(8) N8 0.0488(9) 0.0569(10) 0.0545(9) 0.0173(7) 0.0105(7) 0.0290(8) C25 0.0437(10) 0.0482(10) 0.0407(9) 0.0030(8) -0.0005(7) 0.0209(8) C26 0.0644(13) 0.0415(10) 0.0680(13) 0.0108(9) 0.0087(10) 0.0193(9) C27 0.077(2) 0.0573(13) 0.078(2) 0.0150(11) 0.0075(11) 0.0404(12) C28 0.0607(13) 0.0663(13) 0.0760(10) 0.0127(11) 0.0083(10) 0.0396(11) C29 0.0466(11) 0.0598(12) 0.0694(13) 0.0161(10) 0.0116(9) 0.0258(10) C30 0.0434(10) 0.0575(11) 0.0350(9) 0.0064(8) -0.0009(7) 0.0241(9) C31 0.0469(11) 0.0700(13) 0.0514(11) 0.0056(9) 0.0041(8) 0.0266(10) C32 0.0596(13) 0.089(2) 0.0577(12) 0.0140(11) 0.0097(10) 0.0461(12) C33 0.083(2) 0.081(2) 0.0740(10) 0.0285(12) 0.0226(12) 0.0559(13) C34 0.0730(10) 0.0654(13) 0.0770(10) 0.0295(11) 0.0252(11) 0.0434(12) S1 0.0607(3) 0.0648(3) 0.0484(3) 0.0214(2) 0.0118(2) 0.0358(3) O1 0.0962(11) 0.1003(11) 0.0527(8) 0.0203(8) 0.0225(8) 0.0614(10) O2 0.0862(10) 0.0866(10) 0.0747(9) 0.0408(8) 0.0126(8) 0.0524(9) O3 0.0475(7) 0.0618(8) 0.0601(8) 0.0136(7) -0.0039(6) 0.0095(6) N1 0.0443(9) 0.0562(9) 0.0636(10) 0.0250(8) 0.0129(7) 0.0165(7) C1 0.0367(9) 0.0373(9) 0.0466(9) 0.0095(7) 0.0066(7) 0.0162(7) C2 0.0586(12) 0.0448(10) 0.0563(12) 0.0174(9) 0.0132(9) 0.0197(9) C3 0.0612(13) 0.0430(11) 0.092(2) 0.0232(11) 0.0266(12) 0.0129(10) C4 0.0468(12) 0.0399(11) 0.113(2) 0.0053(12) 0.0112(13) 0.0024(9) C5 0.0502(12) 0.0535(12) 0.0740(10) -0.0029(10) -0.0122(10) 0.0170(10) C6 0.0427(10) 0.0423(9) 0.0512(10) 0.0061(8) 0.0021(8) 0.0214(8) C7 0.0367(9) 0.0420(9) 0.0503(10) 0.0105(8) 0.0051(8) 0.0142(8) S2 0.0586(3) 0.0806(4) 0.0483(3) 0.0167(3) -0.0001(2) 0.0293(3) O4 0.0925(12) 0.140(2) 0.0673(10) 0.0520(10) 0.0293(9) 0.0470(11) O5 0.0832(12) 0.1140(10) 0.0807(11) 0.0058(10) -0.0333(9) 0.0295(10) O6 0.163(2) 0.0907(11) 0.0652(10) 0.0134(8) 0.0207(10) 0.0933(12) N2 0.0743(12) 0.0700(11) 0.0690(11) 0.0260(9) 0.0088(9) 0.0428(9) C8 0.0573(11) 0.0451(10) 0.0486(10) 0.0118(8) 0.0062(8) 0.0244(9) C9 0.101(2) 0.0589(12) 0.0520(12) 0.0143(10) 0.0059(11) 0.0398(12) C10 0.090(2) 0.0592(13) 0.076(2) 0.0217(11) -0.0084(12) 0.0342(12) C11 0.084(2) 0.0553(13) 0.096(2) 0.0086(12) -0.0081(13) 0.0419(12) C12 0.0760(10) 0.0611(13) 0.0660(10) -0.0066(10) 0.0040(11) 0.0361(11) C13 0.0450(10) 0.0500(10) 0.0469(10) 0.0049(8) 0.0001(8) 0.0177(8) C14 0.0800(10) 0.0545(11) 0.0561(12) 0.0136(10) 0.0102(10) 0.0400(11) #=============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4389(19) . . no S1 N1 1.6101(18) . . no S1 O1 1.4395(18) . . no S1 C6 1.7613(19) . . no S2 C13 1.7587(19) . . no S2 O4 1.437(2) . . no S2 N2 1.6045(19) . . no S2 O5 1.425(2) . . no O3 C7 1.250(2) . . no O6 C14 1.246(3) . . no N3 C19 1.336(4) . . no N3 C15 1.327(3) . . no N4 C20 1.360(3) . . no N4 C15 1.390(3) . . no N5 C24 1.345(3) . . no N5 C20 1.342(3) . . no N4 H41 1.02(3) . . no N5 H51 0.94(2) . . no N6 C25 1.323(2) . . no N6 C29 1.343(3) . . no N7 C30 1.356(3) . . no N7 C25 1.390(3) . . no N8 C34 1.349(3) . . no N8 C30 1.336(3) . . no N7 H71 0.93(2) . . no N8 H81 0.90(2) . . no N1 C7 1.342(2) . . no N2 C14 1.330(3) . . no C15 C16 1.392(4) . . no C16 C17 1.365(4) . . no C17 C18 1.381(4) . . no C18 C19 1.360(4) . . no C20 C21 1.399(4) . . no C21 C22 1.356(4) . . no C22 C23 1.382(4) . . no C23 C24 1.350(4) . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C21 H21 0.9500 . . no C22 H22 0.9500 . . no C23 H23 0.9500 . . no C24 H24 0.9500 . . no C25 C26 1.397(3) . . no C26 C27 1.367(4) . . no C27 C28 1.379(4) . . no C28 C29 1.363(4) . . no C30 C31 1.408(3) . . no C31 C32 1.363(4) . . no C32 C33 1.385(4) . . no C33 C34 1.347(4) . . no C26 H26 0.9500 . . no C27 H27 0.9500 . . no C28 H28 0.9500 . . no C29 H29 0.9500 . . no C31 H31 0.9500 . . no C32 H32 0.9500 . . no C33 H33 0.9500 . . no C34 H34 0.9500 . . no C1 C7 1.492(3) . . no C1 C6 1.381(2) . . no C1 C2 1.382(2) . . no C2 C3 1.371(3) . . no C3 C4 1.383(4) . . no C4 C5 1.384(4) . . no C5 C6 1.375(3) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C8 C9 1.387(3) . . no C8 C13 1.365(3) . . no C8 C14 1.495(3) . . no C9 C10 1.379(4) . . no C10 C11 1.378(4) . . no C11 C12 1.372(4) . . no C12 C13 1.386(3) . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 C6 109.99(10) . . . no N1 S1 C6 97.33(9) . . . no O1 S1 N1 111.13(11) . . . no O1 S1 C6 111.10(9) . . . no O1 S1 O2 114.57(9) . . . no O2 S1 N1 111.43(9) . . . no O4 S2 N2 110.73(11) . . . no O4 S2 C13 110.08(11) . . . no O4 S2 O5 115.19(11) . . . no N2 S2 C13 97.31(9) . . . no O5 S2 N2 111.30(11) . . . no O5 S2 C13 110.81(12) . . . no C15 N3 C19 118.1(2) . . . no C15 N4 C20 128.52(19) . . . no C20 N5 C24 122.1(2) . . . no C15 N4 H41 120.8(16) . . . no C20 N4 H41 110.7(16) . . . no C24 N5 H51 129.7(16) . . . no C20 N5 H51 108.2(16) . . . no C25 N6 C29 117.35(18) . . . no C25 N7 C30 128.20(18) . . . no C30 N8 C34 121.9(2) . . . no C25 N7 H71 117.9(14) . . . no C30 N7 H71 113.9(14) . . . no C34 N8 H81 129.1(17) . . . no C30 N8 H81 108.7(17) . . . no S1 N1 C7 111.17(14) . . . no S2 N2 C14 111.25(15) . . . no N3 C15 N4 118.0(2) . . . no N3 C15 C16 122.6(2) . . . no N4 C15 C16 119.4(2) . . . no C15 C16 C17 118.1(2) . . . no C16 C17 C18 119.5(3) . . . no C17 C18 C19 118.7(3) . . . no N3 C19 C18 123.0(3) . . . no N4 C20 N5 120.70(19) . . . no N4 C20 C21 121.1(2) . . . no N5 C20 C21 118.2(2) . . . no C20 C21 C22 119.6(3) . . . no C21 C22 C23 120.6(3) . . . no C22 C23 C24 118.6(3) . . . no N5 C24 C23 120.9(2) . . . no C15 C16 H16 121.00 . . . no C17 C16 H16 121.00 . . . no C18 C17 H17 121.00 . . . no C16 C17 H17 120.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 121.00 . . . no C18 C19 H19 119.00 . . . no N3 C19 H19 118.00 . . . no C20 C21 H21 120.00 . . . no C22 C21 H21 120.00 . . . no C23 C22 H22 120.00 . . . no C21 C22 H22 119.00 . . . no C24 C23 H23 121.00 . . . no C22 C23 H23 120.00 . . . no C23 C24 H24 120.00 . . . no N5 C24 H24 120.00 . . . no N6 C25 C26 122.90(19) . . . no N7 C25 C26 118.96(16) . . . no N6 C25 N7 118.14(15) . . . no C25 C26 C27 118.3(2) . . . no C26 C27 C28 119.2(2) . . . no C27 C28 C29 118.6(2) . . . no N6 C29 C28 123.5(2) . . . no N7 C30 C31 120.2(2) . . . no N7 C30 N8 121.1(2) . . . no N8 C30 C31 118.7(2) . . . no C30 C31 C32 118.8(2) . . . no C31 C32 C33 120.8(2) . . . no C32 C33 C34 118.6(2) . . . no N8 C34 C33 121.1(2) . . . no C27 C26 H26 121.00 . . . no C25 C26 H26 121.00 . . . no C26 C27 H27 120.00 . . . no C28 C27 H27 120.00 . . . no C29 C28 H28 121.00 . . . no C27 C28 H28 121.00 . . . no N6 C29 H29 118.00 . . . no C28 C29 H29 118.00 . . . no C32 C31 H31 121.00 . . . no C30 C31 H31 120.00 . . . no C31 C32 H32 119.00 . . . no C33 C32 H32 120.00 . . . no C32 C33 H33 120.00 . . . no C34 C33 H33 121.00 . . . no C33 C34 H34 119.00 . . . no N8 C34 H34 120.00 . . . no C2 C1 C6 120.02(17) . . . no C2 C1 C7 128.62(15) . . . no C6 C1 C7 111.31(15) . . . no C1 C2 C3 118.44(17) . . . no C2 C3 C4 121.0(2) . . . no C3 C4 C5 121.3(2) . . . no C4 C5 C6 117.0(2) . . . no S1 C6 C5 131.19(17) . . . no S1 C6 C1 106.46(14) . . . no C1 C6 C5 122.28(19) . . . no N1 C7 C1 113.69(16) . . . no O3 C7 N1 124.45(18) . . . no O3 C7 C1 121.83(16) . . . no C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3 119.00 . . . no C4 C3 H3 120.00 . . . no C3 C4 H4 119.00 . . . no C5 C4 H4 119.00 . . . no C4 C5 H5 122.00 . . . no C6 C5 H5 121.00 . . . no C9 C8 C13 120.16(18) . . . no C9 C8 C14 128.3(2) . . . no C13 C8 C14 111.52(17) . . . no C8 C9 C10 118.2(2) . . . no C9 C10 C11 120.6(3) . . . no C10 C11 C12 121.9(3) . . . no C11 C12 C13 116.8(2) . . . no S2 C13 C8 106.36(12) . . . no S2 C13 C12 131.21(16) . . . no C8 C13 C12 122.38(18) . . . no O6 C14 N2 125.6(2) . . . no O6 C14 C8 120.9(2) . . . no N2 C14 C8 113.5(2) . . . no C8 C9 H9 121.00 . . . no C10 C9 H9 121.00 . . . no C9 C10 H10 120.00 . . . no C11 C10 H10 120.00 . . . no C10 C11 H11 119.00 . . . no C12 C11 H11 119.00 . . . no C11 C12 H12 122.00 . . . no C13 C12 H12 122.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 C6 C5 -59.4(2) . . . . no N1 S1 C6 C1 1.54(15) . . . . no N1 S1 C6 C5 -175.4(2) . . . . no O2 S1 N1 C7 -116.95(15) . . . . no C6 S1 N1 C7 -2.07(16) . . . . no O1 S1 C6 C1 -114.52(14) . . . . no O1 S1 C6 C5 68.5(2) . . . . no O2 S1 C6 C1 117.56(14) . . . . no O1 S1 N1 C7 113.96(15) . . . . no O5 S2 C13 C8 116.70(14) . . . . no O4 S2 N2 C14 113.12(17) . . . . no O5 S2 N2 C14 -117.39(18) . . . . no C13 S2 N2 C14 -1.64(17) . . . . no O4 S2 C13 C8 -114.71(15) . . . . no O4 S2 C13 C12 62.6(2) . . . . no O5 S2 C13 C12 -66.0(2) . . . . no N2 S2 C13 C8 0.56(14) . . . . no N2 S2 C13 C12 177.8(2) . . . . no C19 N3 C15 N4 -180.0(2) . . . . no C19 N3 C15 C16 -0.6(3) . . . . no C15 N3 C19 C18 0.2(4) . . . . no C20 N4 C15 C16 -168.8(2) . . . . no C15 N4 C20 N5 -7.8(3) . . . . no C15 N4 C20 C21 172.7(2) . . . . no C20 N4 C15 N3 10.6(3) . . . . no C20 N5 C24 C23 0.3(4) . . . . no C24 N5 C20 N4 179.17(19) . . . . no C24 N5 C20 C21 -1.4(3) . . . . no C29 N6 C25 C26 -0.4(2) . . . . no C29 N6 C25 N7 -179.82(14) . . . . no C25 N6 C29 C28 -1.2(3) . . . . no C30 N7 C25 C26 -171.29(15) . . . . no C25 N7 C30 N8 -5.3(3) . . . . no C25 N7 C30 C31 173.95(16) . . . . no C30 N7 C25 N6 8.2(3) . . . . no C30 N8 C34 C33 -0.1(4) . . . . no C34 N8 C30 N7 178.78(19) . . . . no C34 N8 C30 C31 -0.5(3) . . . . no S1 N1 C7 O3 179.92(15) . . . . no S1 N1 C7 C1 2.0(2) . . . . no S2 N2 C14 O6 -179.1(2) . . . . no S2 N2 C14 C8 2.2(2) . . . . no N4 C15 C16 C17 179.8(2) . . . . no N3 C15 C16 C17 0.4(3) . . . . no C15 C16 C17 C18 0.1(4) . . . . no C16 C17 C18 C19 -0.5(4) . . . . no C17 C18 C19 N3 0.3(4) . . . . no N5 C20 C21 C22 1.5(3) . . . . no N4 C20 C21 C22 -179.1(2) . . . . no C20 C21 C22 C23 -0.5(4) . . . . no C21 C22 C23 C24 -0.6(4) . . . . no C22 C23 C24 N5 0.7(4) . . . . no N7 C25 C26 C27 -179.44(18) . . . . no N6 C25 C26 C27 1.1(3) . . . . no C25 C26 C27 C28 -0.4(3) . . . . no C26 C27 C28 C29 -1.1(4) . . . . no C27 C28 C29 N6 1.9(3) . . . . no N7 C30 C31 C32 -178.99(15) . . . . no N8 C30 C31 C32 0.3(2) . . . . no C30 C31 C32 C33 0.5(3) . . . . no C31 C32 C33 C34 -1.0(3) . . . . no C32 C33 C34 N8 0.8(4) . . . . no C2 C1 C6 C5 -1.1(3) . . . . no C7 C1 C6 S1 -0.62(19) . . . . no C7 C1 C6 C5 176.70(19) . . . . no C2 C1 C7 O3 -1.3(3) . . . . no C6 C1 C2 C3 1.1(3) . . . . no C7 C1 C2 C3 -176.2(2) . . . . no C2 C1 C6 S1 -178.40(14) . . . . no C6 C1 C7 N1 -0.8(2) . . . . no C2 C1 C7 N1 176.72(19) . . . . no C6 C1 C7 O3 -178.81(17) . . . . no C1 C2 C3 C4 -0.4(3) . . . . no C2 C3 C4 C5 -0.5(4) . . . . no C3 C4 C5 C6 0.6(4) . . . . no C4 C5 C6 S1 176.81(18) . . . . no C4 C5 C6 C1 0.2(3) . . . . no C13 C8 C9 C10 -0.3(4) . . . . no C14 C8 C9 C10 176.6(2) . . . . no C9 C8 C13 S2 177.99(18) . . . . no C9 C8 C13 C12 0.4(3) . . . . no C14 C8 C13 S2 0.56(19) . . . . no C14 C8 C13 C12 -177.00(19) . . . . no C9 C8 C14 O6 2.2(4) . . . . no C9 C8 C14 N2 -179.0(2) . . . . no C13 C8 C14 O6 179.4(2) . . . . no C13 C8 C14 N2 -1.8(3) . . . . no C8 C9 C10 C11 0.0(4) . . . . no C9 C10 C11 C12 0.3(4) . . . . no C10 C11 C12 C13 -0.2(4) . . . . no C11 C12 C13 S2 -177.06(19) . . . . no C11 C12 C13 C8 -0.2(3) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N4 H41 O6 1.02(3) 1.72(3) 2.722(2) 168(2) 2_655 yes N5 H51 N3 0.94(2) 1.84(2) 2.658(3) 145(2) . yes N7 H71 O3 0.93(2) 1.78(2) 2.708(2) 173.9(13) 1_655 yes N8 H81 N6 0.90(2) 1.88(2) 2.651(3) 143(2) . yes C5 H5 O5 0.9500 2.3100 3.184(3) 153.00 2_666 yes C22 H22 O4 0.9500 2.3900 3.181(4) 140.00 1_655 yes C32 H32 O2 0.9500 2.4000 3.209(3) 143.00 2_656 yes #===END