#CIF-file_Pyridinium dihydrogenmonothiophosphate #============================================================================== data_Pyridiniumdihydrogenmonothiophosphate _publ_requested_journal 'The Journal of Organic Chemistry' _publ_contact_author_name 'Prof. Jan Bergman' _publ_contact_author_address ; Department of Biosciences and Nutrition Karolinska Institutet SE 141 57 Huddinge, Sweden ; _publ_contact_author_email jan.bergman@ki.se loop_ _publ_author_name _publ_author_address 'Bergman, Jan ' ; Department of Biosciences and Nutrition Karolinska Institutet SE 141 57 Huddinge, Sweden ; 'Pettersson, Birgitta' ; Department of Biosciences and Nutrition Karolinska Institutet SE 141 57 Huddinge, Sweden ; 'Hasimbegovic, Vedran' ; Department of Biosciences and Nutrition Karolinska Institutet SE 141 57 Huddinge, Sweden ; 'Svensson, Per H.' ; AstraZeneca R&D Sodertalje Pharmaceutical Development, B341:3, SE 151 85 Sodertalje Sweden ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyridinium dihydrogenmonothiophosphate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H6 N, H2 O3 P S' _chemical_formula_sum 'C5 H8 N O3 P S ' _chemical_formula_weight 193.16 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' 'P' 'P' 0.1023 0.0942 '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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9234(4) _cell_length_b 11.0214(5) _cell_length_c 9.0941(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.514(2) _cell_angle_gamma 90.00 _cell_volume 790.49(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9957 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.58 _exptl_crystal_description Block _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.568 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20537 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.58 _reflns_number_total 1820 _reflns_number_gt 1711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.3826P] 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 const. _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.036(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1820 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.11919(4) 0.67414(3) 0.07600(3) 0.01689(14) Uani 1 1 d . . . S1 S 0.29244(4) 0.55296(3) 0.03519(3) 0.02303(14) Uani 1 1 d . . . O1 O 0.03748(12) 0.73426(9) -0.07043(10) 0.0270(2) Uani 1 1 d . . . H8 H 0.0974 0.7212 -0.1512 0.061(6) Uiso 1 1 d R . . O2 O -0.03595(11) 0.61534(8) 0.14709(9) 0.0227(2) Uani 1 1 d . . . H7 H -0.1025 0.5631 0.0886 0.039(5) Uiso 1 1 d R . . O3 O 0.18147(12) 0.77289(8) 0.18390(10) 0.0245(2) Uani 1 1 d . . . N1 N 0.73800(14) 0.48814(10) 0.42550(12) 0.0224(3) Uani 1 1 d . . . H6 H 0.7750 0.4195 0.3908 0.027 Uiso 1 1 calc R . . C3 C 0.62683(19) 0.70061(13) 0.53063(16) 0.0271(3) Uani 1 1 d . . . H3 H 0.5887 0.7756 0.5669 0.032 Uiso 1 1 calc R . . C5 C 0.79949(16) 0.52493(13) 0.56074(15) 0.0237(3) Uani 1 1 d . . . H5 H 0.8801 0.4764 0.6182 0.028 Uiso 1 1 calc R . . C1 C 0.62205(17) 0.55253(12) 0.34152(15) 0.0246(3) Uani 1 1 d . . . H1 H 0.5806 0.5238 0.2464 0.029 Uiso 1 1 calc R . . C2 C 0.56345(18) 0.65952(12) 0.39280(15) 0.0264(3) Uani 1 1 d . . . H2 H 0.4802 0.7051 0.3344 0.032 Uiso 1 1 calc R . . C4 C 0.74607(17) 0.63238(13) 0.61599(14) 0.0258(3) Uani 1 1 d . . . H4 H 0.7900 0.6597 0.7111 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0215(2) 0.0176(2) 0.01161(19) -0.00072(11) 0.00181(13) -0.00223(12) S1 0.0215(2) 0.0237(2) 0.0231(2) -0.00300(12) -0.00136(13) 0.00110(12) O1 0.0323(6) 0.0345(5) 0.0148(5) 0.0041(4) 0.0053(4) 0.0115(4) O2 0.0237(5) 0.0270(5) 0.0181(4) -0.0039(4) 0.0056(3) -0.0067(4) O3 0.0346(6) 0.0225(5) 0.0171(5) -0.0040(4) 0.0055(4) -0.0084(4) N1 0.0241(6) 0.0192(5) 0.0248(6) 0.0004(4) 0.0072(4) 0.0017(4) C3 0.0321(8) 0.0214(6) 0.0291(7) -0.0021(6) 0.0096(6) 0.0011(6) C5 0.0192(7) 0.0274(7) 0.0245(7) 0.0069(6) 0.0016(5) 0.0000(5) C1 0.0240(7) 0.0312(7) 0.0187(6) 0.0009(5) 0.0032(5) -0.0014(5) C2 0.0236(7) 0.0287(7) 0.0269(7) 0.0071(5) 0.0032(5) 0.0050(5) C4 0.0267(7) 0.0284(7) 0.0221(7) -0.0022(6) 0.0017(5) -0.0071(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 P1 O3 1.5159(9) . ? P1 O1 1.5703(9) . ? P1 O2 1.5817(9) . ? P1 S1 1.9758(5) . ? O1 H8 0.9232 . ? O2 H7 0.9153 . ? N1 C5 1.3414(18) . ? N1 C1 1.3403(17) . ? N1 H6 0.8800 . ? C3 C2 1.381(2) . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C5 C4 1.3693(19) . ? C5 H5 0.9500 . ? C1 C2 1.3656(19) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C4 H4 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 P1 O1 109.15(5) . . ? O3 P1 O2 104.30(5) . . ? O1 P1 O2 104.25(5) . . ? O3 P1 S1 114.71(4) . . ? O1 P1 S1 111.30(4) . . ? O2 P1 S1 112.40(4) . . ? P1 O1 H8 114.0 . . ? P1 O2 H7 116.6 . . ? C5 N1 C1 122.08(12) . . ? C5 N1 H6 119.0 . . ? C1 N1 H6 119.0 . . ? C2 C3 C4 119.96(13) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? N1 C5 C4 120.00(12) . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? N1 C1 C2 119.97(13) . . ? N1 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 119.15(13) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C5 C4 C3 118.82(13) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.266 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.049