#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/60/4026097.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4026097
loop_
_publ_author_name
'Jan Bergman'
'Birgitta Pettersson'
'Vedran Hasimbegovic'
'Per H. Svensson'
_publ_contact_author_address
;
Department of Biosciences and Nutrition
Karolinska Institutet
SE 141 57 Huddinge,
Sweden
;
_publ_contact_author_email       jan.bergman@ki.se
_publ_contact_author_name        'Prof. Jan Bergman'
_publ_section_title
;
 Thionations Using a P4S10-Pyridine Complex in Solvents Such as
 Acetonitrile and Dimethyl Sulfone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1546
_journal_page_last               1553
_journal_paper_doi               10.1021/jo101865y
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C5 H6 N, H2 O3 P S'
_chemical_formula_sum            'C5 H8 N O3 P S'
_chemical_formula_weight         193.16
_chemical_name_systematic
; 
Pyridinium dihydrogenmonothiophosphate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.514(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9234(4)
_cell_length_b                   11.0214(5)
_cell_length_c                   9.0941(3)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.58
_cell_volume                     790.49(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20537
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_meas      0
_exptl_crystal_description       Block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.036(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    const.
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.3826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                1711
_reflns_number_total             1820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101865y_si_002.cif
_cod_data_source_block           Pyridiniumdihydrogenmonothiophosphate
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_formula_sum        'C5 H8 N O3 P S '
_cod_database_code               4026097
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'
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
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)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652277
