data_sulphate salt of m-xylyeneguanidinium _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common m-xylyenediguanidinium sulfate _chemical_melting_point 335 decomp. _chemical_formula_moiety C10 H18 O4 S1 _chemical_formula_sum 'C10 H18 N6 O4 S' _chemical_formula_weight 318.36 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.057(2) _cell_length_b 13.059(3) _cell_length_c 19.496(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2815.1(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15mm _exptl_crystal_size_mid 0.05mm _exptl_crystal_size_min 0.02mm _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.612 _exptl_absorpt_correction_T_max 7 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Crysta (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25570 _diffrn_reflns_av_R_equivalents 0.1346 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2491 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection loop_ ' DENZO (Otwinoski and Minor, 1997)' ' COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin and Pearce, 1995)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2491 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1287 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 0.838 _refine_ls_restrained_S_all 0.838 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.17186(6) 0.86717(5) 0.38220(4) 0.0190(2) Uani 1 1 d . . . O1 O 0.18093(16) 0.75910(15) 0.35909(10) 0.0227(5) Uani 1 1 d . . . O3 O 0.15451(17) 0.86800(15) 0.45724(10) 0.0237(5) Uani 1 1 d . . . N6 N 0.8000(2) 0.77710(19) 0.47257(13) 0.0236(6) Uani 1 1 d . . . O2 O 0.06696(17) 0.91605(15) 0.34909(11) 0.0283(5) Uani 1 1 d . . . O4 O 0.28400(17) 0.92073(16) 0.36477(11) 0.0298(5) Uani 1 1 d . . . N1 N 0.4364(2) 0.8000(2) 0.26847(15) 0.0245(6) Uani 1 1 d . . . N5 N 0.8759(2) 0.9427(2) 0.47084(15) 0.0254(6) Uani 1 1 d . . . N4 N 0.7140(2) 0.9002(2) 0.53978(14) 0.0241(6) Uani 1 1 d . . . C8 C 0.7536(3) 0.6441(2) 0.34640(16) 0.0226(7) Uani 1 1 d . . . C10 C 0.7991(2) 0.8735(2) 0.49406(15) 0.0208(6) Uani 1 1 d . . . C1 C 0.4708(2) 0.7039(2) 0.28248(14) 0.0202(7) Uani 1 1 d . . . N2 N 0.4118(3) 0.6521(2) 0.33105(14) 0.0270(6) Uani 1 1 d . . . N3 N 0.5621(2) 0.66429(19) 0.24859(14) 0.0228(6) Uani 1 1 d . . . C3 C 0.7167(2) 0.5592(2) 0.30979(14) 0.0202(7) Uani 1 1 d . . . C5 C 0.8740(3) 0.4605(2) 0.36428(16) 0.0263(7) Uani 1 1 d . . . C9 C 0.8940(3) 0.7338(3) 0.42871(18) 0.0299(7) Uani 1 1 d . . . C7 C 0.8513(2) 0.6384(2) 0.39260(15) 0.0243(7) Uani 1 1 d . . . C6 C 0.9099(3) 0.5459(2) 0.40101(16) 0.0257(7) Uani 1 1 d . . . C4 C 0.7790(3) 0.4673(2) 0.31843(16) 0.0239(7) Uani 1 1 d . . . C2 C 0.6131(3) 0.5633(2) 0.25874(17) 0.0243(7) Uani 1 1 d . . . H5 H 0.550(2) 0.517(2) 0.2727(13) 0.014(7) Uiso 1 1 d . . . H8 H 0.978(3) 0.539(2) 0.4339(16) 0.030(8) Uiso 1 1 d . . . H4 H 0.640(3) 0.538(2) 0.2149(17) 0.025(8) Uiso 1 1 d . . . H10 H 0.920(3) 0.784(3) 0.3975(17) 0.030(9) Uiso 1 1 d . . . H6 H 0.754(2) 0.407(2) 0.2953(16) 0.019(7) Uiso 1 1 d . . . H9 H 0.708(3) 0.712(3) 0.3407(16) 0.032(8) Uiso 1 1 d . . . H7 H 0.918(3) 0.397(3) 0.3717(17) 0.038(9) Uiso 1 1 d . . . H2 H 0.389(3) 0.830(3) 0.2973(19) 0.037(10) Uiso 1 1 d . . . H13 H 0.679(3) 0.847(3) 0.5638(18) 0.040(10) Uiso 1 1 d . . . H11 H 0.742(3) 0.730(3) 0.4905(19) 0.046(10) Uiso 1 1 d . . . H3 H 0.595(3) 0.700(3) 0.2168(19) 0.035(10) Uiso 1 1 d . . . H12 H 0.872(3) 1.009(3) 0.4885(16) 0.027(8) Uiso 1 1 d . . . H1 H 0.346(4) 0.675(3) 0.342(2) 0.047(11) Uiso 1 1 d . . . H17 H 0.479(3) 0.833(3) 0.237(2) 0.050(11) Uiso 1 1 d . . . H15 H 0.963(3) 0.720(3) 0.4560(18) 0.044(10) Uiso 1 1 d . . . H16 H 0.424(3) 0.587(3) 0.3373(17) 0.028(9) Uiso 1 1 d . . . H19 H 0.716(3) 0.958(3) 0.5564(17) 0.023(9) Uiso 1 1 d . . . H30 H 0.925(3) 0.930(3) 0.443(2) 0.038(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0181(4) 0.0180(4) 0.0210(4) -0.0007(3) -0.0007(3) 0.0004(3) O1 0.0244(10) 0.0192(11) 0.0244(12) -0.0061(8) -0.0033(8) -0.0004(8) O3 0.0291(11) 0.0217(11) 0.0204(11) -0.0001(9) 0.0025(8) 0.0025(8) N6 0.0231(13) 0.0217(15) 0.0261(15) -0.0051(11) 0.0060(10) -0.0045(11) O2 0.0283(12) 0.0238(12) 0.0329(13) 0.0040(9) -0.0080(9) 0.0044(9) O4 0.0258(11) 0.0279(13) 0.0357(14) -0.0035(10) 0.0081(9) -0.0080(9) N1 0.0258(14) 0.0217(15) 0.0260(16) -0.0001(12) 0.0060(12) 0.0012(11) N5 0.0246(14) 0.0210(16) 0.0304(16) -0.0049(12) 0.0058(12) -0.0043(11) N4 0.0244(14) 0.0217(16) 0.0261(16) -0.0031(13) 0.0039(11) -0.0023(11) C8 0.0227(15) 0.0188(16) 0.0264(18) 0.0016(13) 0.0074(12) -0.0003(12) C10 0.0193(13) 0.0230(17) 0.0200(16) 0.0000(13) -0.0044(11) 0.0003(12) C1 0.0205(14) 0.0191(16) 0.0211(17) -0.0019(13) -0.0034(11) -0.0009(11) N2 0.0247(14) 0.0273(17) 0.0291(16) 0.0063(12) 0.0071(11) 0.0032(12) N3 0.0225(13) 0.0247(14) 0.0213(15) 0.0038(11) 0.0075(10) 0.0018(11) C3 0.0208(14) 0.0204(16) 0.0195(16) -0.0021(12) 0.0075(11) -0.0001(12) C5 0.0259(16) 0.0216(18) 0.0313(19) -0.0012(14) 0.0013(13) 0.0039(13) C9 0.0251(17) 0.0309(19) 0.034(2) -0.0070(16) 0.0033(14) -0.0018(14) C7 0.0214(14) 0.0287(18) 0.0229(17) -0.0034(13) 0.0080(12) -0.0042(12) C6 0.0202(15) 0.0308(19) 0.0262(17) 0.0007(14) 0.0001(12) -0.0004(12) C4 0.0262(15) 0.0201(17) 0.0256(18) -0.0038(14) 0.0041(12) -0.0009(12) C2 0.0230(16) 0.0223(17) 0.0276(18) -0.0003(14) 0.0026(13) -0.0015(13) _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 O4 1.464(2) . ? S1 O2 1.473(2) . ? S1 O3 1.475(2) . ? S1 O1 1.485(2) . ? N6 C10 1.326(4) . ? N6 C9 1.460(4) . ? N1 C1 1.339(4) . ? N5 C10 1.320(4) . ? N4 C10 1.342(4) . ? C8 C3 1.380(4) . ? C8 C7 1.409(4) . ? C1 N3 1.313(4) . ? C1 N2 1.334(4) . ? N3 C2 1.448(4) . ? C3 C4 1.395(4) . ? C3 C2 1.518(4) . ? C5 C4 1.382(4) . ? C5 C6 1.383(4) . ? C9 C7 1.506(4) . ? C7 C6 1.381(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O2 110.99(12) . . ? O4 S1 O3 109.69(12) . . ? O2 S1 O3 109.21(12) . . ? O4 S1 O1 109.05(12) . . ? O2 S1 O1 109.39(12) . . ? O3 S1 O1 108.46(12) . . ? C10 N6 C9 123.9(2) . . ? C3 C8 C7 121.0(3) . . ? N5 C10 N6 122.5(3) . . ? N5 C10 N4 120.0(3) . . ? N6 C10 N4 117.5(3) . . ? N3 C1 N2 122.2(3) . . ? N3 C1 N1 119.0(3) . . ? N2 C1 N1 118.8(3) . . ? C1 N3 C2 126.2(3) . . ? C8 C3 C4 118.9(3) . . ? C8 C3 C2 122.3(3) . . ? C4 C3 C2 118.8(3) . . ? C4 C5 C6 120.1(3) . . ? N6 C9 C7 111.8(2) . . ? C6 C7 C8 118.8(3) . . ? C6 C7 C9 121.4(3) . . ? C8 C7 C9 119.7(3) . . ? C7 C6 C5 120.6(3) . . ? C5 C4 C3 120.6(3) . . ? N3 C2 C3 114.6(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.227 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.064