data_kyd1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'diphenylammonium sulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O4 S' _chemical_formula_weight 267.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5292(17) _cell_length_b 9.4437(18) _cell_length_c 9.5965(18) _cell_angle_alpha 61.113(2) _cell_angle_beta 78.878(6) _cell_angle_gamma 64.120(9) _cell_volume 608.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9476 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4447 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2974 _reflns_number_gt 2797 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[?^2^(Fo^2^)+(0.0948P)^2^+0.1163P] 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 2974 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 1.252 _refine_ls_restrained_S_all 1.252 _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 N1 N 0.56932(17) 0.30253(18) 0.36587(16) 0.0215(3) Uani 1 1 d . . . H3 H 0.5823 0.4058 0.3331 0.026 Uiso 1 1 d R . . H4 H 0.5682 0.2499 0.4753 0.026 Uiso 1 1 d R . . C1 C 0.7232(2) 0.1861(2) 0.31682(19) 0.0208(3) Uani 1 1 d . . . C2 C 0.8054(2) 0.0118(2) 0.4262(2) 0.0287(4) Uani 1 1 d . . . H5 H 0.7624 -0.0324 0.5308 0.034 Uiso 1 1 calc R . . C3 C 0.9524(3) -0.0975(2) 0.3797(2) 0.0347(4) Uani 1 1 d . . . H6 H 1.0112 -0.2175 0.4533 0.042 Uiso 1 1 calc R . . C4 C 1.0135(2) -0.0325(3) 0.2270(2) 0.0324(4) Uani 1 1 d . . . H7 H 1.1136 -0.1082 0.1961 0.039 Uiso 1 1 calc R . . C5 C 0.9293(2) 0.1423(3) 0.1190(2) 0.0323(4) Uani 1 1 d . . . H8 H 0.9718 0.1862 0.0142 0.039 Uiso 1 1 calc R . . C6 C 0.7823(2) 0.2541(2) 0.1634(2) 0.0279(4) Uani 1 1 d . . . H9 H 0.7238 0.3743 0.0900 0.033 Uiso 1 1 calc R . . C7 C 0.3980(2) 0.3483(2) 0.30676(18) 0.0208(3) Uani 1 1 d . . . C8 C 0.3822(2) 0.2710(2) 0.2221(2) 0.0244(3) Uani 1 1 d . . . H10 H 0.4822 0.1883 0.1986 0.029 Uiso 1 1 calc R . . C9 C 0.2169(2) 0.3168(2) 0.1721(2) 0.0283(4) Uani 1 1 d . . . H11 H 0.2037 0.2662 0.1126 0.034 Uiso 1 1 calc R . . C10 C 0.0713(2) 0.4358(2) 0.2084(2) 0.0289(4) Uani 1 1 d . . . H12 H -0.0414 0.4654 0.1750 0.035 Uiso 1 1 calc R . . C11 C 0.0900(2) 0.5121(3) 0.2938(2) 0.0312(4) Uani 1 1 d . . . H13 H -0.0097 0.5945 0.3178 0.037 Uiso 1 1 calc R . . C12 C 0.2539(2) 0.4678(2) 0.3437(2) 0.0284(4) Uani 1 1 d . . . H14 H 0.2675 0.5187 0.4027 0.034 Uiso 1 1 calc R . . S1 S 0.45092(5) 0.22435(5) 0.78984(4) 0.02176(17) Uani 1 1 d . . . O1 O 0.31070(18) 0.1558(2) 0.86943(19) 0.0381(3) Uani 1 1 d . . . H1 H 0.3538 0.0487 0.9299 0.057 Uiso 1 1 d R . . O2 O 0.55163(19) 0.14216(18) 0.68956(16) 0.0350(3) Uani 1 1 d . . . O3 O 0.36378(18) 0.41451(17) 0.70226(18) 0.0334(3) Uani 1 1 d . . . O4 O 0.56508(18) 0.17768(19) 0.91866(16) 0.0332(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0224(6) 0.0223(6) 0.0228(6) -0.0135(5) 0.0013(5) -0.0079(5) C1 0.0195(7) 0.0218(7) 0.0233(7) -0.0127(6) 0.0022(5) -0.0079(6) C2 0.0304(9) 0.0250(8) 0.0244(8) -0.0107(7) 0.0047(6) -0.0081(7) C3 0.0320(9) 0.0264(8) 0.0376(10) -0.0157(8) 0.0016(7) -0.0039(7) C4 0.0236(8) 0.0380(9) 0.0424(10) -0.0277(9) 0.0082(7) -0.0101(7) C5 0.0309(9) 0.0426(10) 0.0296(9) -0.0203(8) 0.0127(7) -0.0200(8) C6 0.0296(8) 0.0273(8) 0.0256(8) -0.0110(7) 0.0059(6) -0.0136(7) C7 0.0213(7) 0.0207(7) 0.0193(7) -0.0093(6) 0.0009(5) -0.0075(6) C8 0.0240(8) 0.0270(8) 0.0264(8) -0.0166(7) 0.0036(6) -0.0098(6) C9 0.0303(9) 0.0326(9) 0.0279(8) -0.0166(7) 0.0002(6) -0.0140(7) C10 0.0244(8) 0.0330(9) 0.0273(8) -0.0117(7) -0.0018(6) -0.0110(7) C11 0.0237(8) 0.0327(9) 0.0348(9) -0.0198(8) 0.0002(7) -0.0039(7) C12 0.0262(8) 0.0294(8) 0.0323(9) -0.0203(7) -0.0005(6) -0.0057(7) S1 0.0228(2) 0.0223(2) 0.0221(2) -0.01323(18) 0.00338(15) -0.00825(17) O1 0.0291(7) 0.0387(7) 0.0458(8) -0.0159(6) 0.0064(6) -0.0189(6) O2 0.0409(7) 0.0337(7) 0.0253(6) -0.0195(6) 0.0044(5) -0.0052(6) O3 0.0326(7) 0.0228(6) 0.0440(8) -0.0154(6) -0.0037(6) -0.0082(5) O4 0.0315(7) 0.0434(8) 0.0312(7) -0.0220(6) -0.0014(5) -0.0136(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 N1 C1 1.4684(19) . ? N1 C7 1.475(2) . ? N1 H3 0.9200 . ? N1 H4 0.9199 . ? C1 C2 1.382(2) . ? C1 C6 1.384(2) . ? C2 C3 1.392(2) . ? C2 H5 0.9500 . ? C3 C4 1.382(3) . ? C3 H6 0.9500 . ? C4 C5 1.383(3) . ? C4 H7 0.9500 . ? C5 C6 1.393(2) . ? C5 H8 0.9500 . ? C6 H9 0.9500 . ? C7 C8 1.383(2) . ? C7 C12 1.385(2) . ? C8 C9 1.390(2) . ? C8 H10 0.9500 . ? C9 C10 1.386(2) . ? C9 H11 0.9500 . ? C10 C11 1.392(3) . ? C10 H12 0.9500 . ? C11 C12 1.383(2) . ? C11 H13 0.9500 . ? C12 H14 0.9500 . ? S1 O2 1.4447(13) . ? S1 O3 1.4496(13) . ? S1 O4 1.4946(13) . ? S1 O1 1.5096(14) . ? O1 H1 0.8277 . ? 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 C1 N1 C7 117.05(12) . . ? C1 N1 H3 108.0 . . ? C7 N1 H3 108.0 . . ? C1 N1 H4 108.1 . . ? C7 N1 H4 108.1 . . ? H3 N1 H4 107.2 . . ? C2 C1 C6 122.10(15) . . ? C2 C1 N1 118.70(14) . . ? C6 C1 N1 119.19(15) . . ? C1 C2 C3 118.46(16) . . ? C1 C2 H5 120.8 . . ? C3 C2 H5 120.8 . . ? C4 C3 C2 120.44(17) . . ? C4 C3 H6 119.8 . . ? C2 C3 H6 119.8 . . ? C3 C4 C5 120.25(16) . . ? C3 C4 H7 119.9 . . ? C5 C4 H7 119.9 . . ? C4 C5 C6 120.23(16) . . ? C4 C5 H8 119.9 . . ? C6 C5 H8 119.9 . . ? C1 C6 C5 118.52(16) . . ? C1 C6 H9 120.7 . . ? C5 C6 H9 120.7 . . ? C8 C7 C12 121.71(15) . . ? C8 C7 N1 121.21(14) . . ? C12 C7 N1 117.06(14) . . ? C7 C8 C9 118.60(15) . . ? C7 C8 H10 120.7 . . ? C9 C8 H10 120.7 . . ? C10 C9 C8 120.45(16) . . ? C10 C9 H11 119.8 . . ? C8 C9 H11 119.8 . . ? C9 C10 C11 120.02(16) . . ? C9 C10 H12 120.0 . . ? C11 C10 H12 120.0 . . ? C12 C11 C10 119.98(16) . . ? C12 C11 H13 120.0 . . ? C10 C11 H13 120.0 . . ? C11 C12 C7 119.23(16) . . ? C11 C12 H14 120.4 . . ? C7 C12 H14 120.4 . . ? O2 S1 O3 113.03(8) . . ? O2 S1 O4 110.07(8) . . ? O3 S1 O4 109.74(8) . . ? O2 S1 O1 109.67(9) . . ? O3 S1 O1 106.83(8) . . ? O4 S1 O1 107.30(9) . . ? S1 O1 H1 111.0 . . ? 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 N1 C1 C2 -104.75(17) . . . . ? C7 N1 C1 C6 75.70(19) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? N1 C1 C2 C3 -179.25(17) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? N1 C1 C6 C5 179.50(15) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? C1 N1 C7 C8 6.2(2) . . . . ? C1 N1 C7 C12 -175.61(14) . . . . ? C12 C7 C8 C9 0.6(3) . . . . ? N1 C7 C8 C9 178.78(15) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C8 C7 C12 C11 -0.5(3) . . . . ? N1 C7 C12 C11 -178.68(16) . . . . ? 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 H3 O3 0.92 1.81 2.719(2) 169.7 2_666 N1 H3 S1 0.92 2.99 3.8988(16) 168.6 2_666 N1 H4 O2 0.92 1.81 2.7274(19) 175.3 . N1 H4 S1 0.92 2.92 3.7791(16) 156.6 . O1 H1 O4 0.83 1.80 2.628(2) 172.9 2_657 O1 H1 S1 0.83 2.82 3.5447(17) 147.8 2_657 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.700 _refine_diff_density_min -1.104 _refine_diff_density_rms 0.288