#------------------------------------------------------------------------------
#$Date: 2019-12-25 20:39:37 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245647 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/11/2311175.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311175
loop_
_publ_author_name
'Akkurt, Mehmet'
'Akkoç, Senem'
'Gök, Yetkin'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 1,3-Bis[(5-amino-furan-2-yl)meth-yl]-3,4,5,6-tetra-hydro-pyrimidin-1-ium
 hexa-fluoro-phosphate.
;
_journal_coeditor_code           HG5332
_journal_issue                   'Pt 8'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o1325
_journal_paper_doi               10.1107/S1600536813020187
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H21 N2 O2 +, P F6 -'
_chemical_formula_moiety         'C16 H21 N2 O2 +, F6 P -'
_chemical_formula_sum            'C16 H21 F6 N2 O2 P'
_chemical_formula_weight         418.32
_chemical_name_systematic
;
1,3-Bis[(5-aminofuran-2-yl)methyl]-3,4,5,6-tetrahydropyrimidin-1-ium
hexafluorophosphate
;
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.747(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0793(6)
_cell_length_b                   18.879(2)
_cell_length_c                   8.5750(9)
_cell_measurement_reflns_used    1100
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     966.90(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1677
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        24.74
_diffrn_reflns_theta_max         24.74
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(XABS2; Parkin et al., 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1389P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2473
_reflns_number_gt                1089
_reflns_number_total             1677
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5332sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2311175
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.0509(5) 0.46898(16) 0.2298(3) 0.0808(11) Uani d . 1.000
N N1 -0.1021(5) 0.31127(19) 0.1262(4) 0.0706(11) Uani d . 1.000
C C1 -0.0850(8) 0.25000 0.0606(6) 0.069(2) Uani d S 1.000
C C2 -0.1511(9) 0.3154(3) 0.2862(5) 0.0872(17) Uani d . 1.000
C C3 -0.2709(14) 0.25000 0.3206(9) 0.106(3) Uani d S 1.000
C C4 -0.0792(7) 0.3771(2) 0.0383(5) 0.0817(16) Uani d . 1.000
C C5 0.1016(7) 0.4235(2) 0.1168(5) 0.0725(16) Uani d . 1.000
C C6 0.3108(8) 0.4325(3) 0.1001(6) 0.091(2) Uani d . 1.000
C C7 0.4019(9) 0.4871(3) 0.2040(6) 0.094(2) Uani d . 1.000
C C8 0.2431(9) 0.5075(3) 0.2828(5) 0.0852(17) Uani d . 1.000
C C9 0.2247(12) 0.5625(3) 0.4039(7) 0.120(3) Uani d . 1.000
P P1 0.3506(2) 0.25000 0.73427(19) 0.0793(7) Uani d S 1.000
F F1 0.3265(10) 0.25000 0.5584(6) 0.247(6) Uani d S 1.000
F F2 0.0993(9) 0.25000 0.7207(8) 0.236(6) Uani d S 1.000
F F3 0.3704(10) 0.25000 0.9155(7) 0.218(5) Uani d S 1.000
F F4 0.6000(9) 0.25000 0.7399(8) 0.260(7) Uani d S 1.000
F F5 0.449(3) 0.3183(5) 0.7947(15) 0.204(7) Uani d P 0.500
F F6 0.258(3) 0.3213(5) 0.699(2) 0.260(8) Uani d P 0.500
H H1 -0.05810 0.25000 -0.04260 0.0820 Uiso c SR 1.000
H H2A -0.24330 0.35660 0.29500 0.1050 Uiso c R 1.000
H H2B -0.01270 0.32020 0.36270 0.1050 Uiso c R 1.000
H H3A -0.28490 0.25000 0.43150 0.1280 Uiso c SR 1.000
H H3B -0.42050 0.25000 0.25680 0.1280 Uiso c SR 1.000
H H4A -0.05180 0.36490 -0.06630 0.0980 Uiso c R 1.000
H H4B -0.21940 0.40290 0.02440 0.0980 Uiso c R 1.000
H H6 0.38470 0.40730 0.03220 0.1090 Uiso c R 1.000
H H7 0.54600 0.50550 0.21560 0.1130 Uiso c R 1.000
H H9A 0.36010 0.58990 0.42480 0.1800 Uiso c R 1.000
H H9B 0.20190 0.54010 0.50010 0.1800 Uiso c R 1.000
H H9C 0.10040 0.59310 0.36490 0.1800 Uiso c R 1.000
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'
F F 0.0171 0.0103 ' 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'
P P 0.1023 0.0942 ' 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F4 P1 F5 . 4_555 69.5(7) no
F4 P1 F6 . 4_555 110.6(7) no
F5 P1 F6 . . 52.1(9) no
F5 P1 F5 . 4_555 122.0(8) no
F5 P1 F6 . 4_555 171.5(8) no
F5 P1 F6 4_555 . 171.5(8) no
F6 P1 F6 . 4_555 132.9(9) no
F5 P1 F6 4_555 4_555 52.1(9) no
F2 P1 F5 . 4_555 111.4(7) no
F2 P1 F6 . 4_555 69.0(7) no
F3 P1 F4 . . 94.5(4) no
F3 P1 F5 . . 72.2(5) no
F1 P1 F2 . . 90.9(4) no
F1 P1 F3 . . 178.9(3) no
F1 P1 F4 . . 86.6(4) no
F1 P1 F5 . . 108.3(5) no
F1 P1 F6 . . 80.2(7) no
F1 P1 F5 . 4_555 108.3(5) no
F1 P1 F6 . 4_555 80.2(7) no
F2 P1 F3 . . 88.0(4) no
F2 P1 F4 . . 177.5(4) no
F2 P1 F5 . . 111.4(7) no
F2 P1 F6 . . 69.0(7) no
F4 P1 F5 . . 69.5(7) no
F4 P1 F6 . . 110.6(7) no
F3 P1 F5 . 4_555 72.2(5) no
F3 P1 F6 . 4_555 99.4(7) no
F3 P1 F6 . . 99.4(7) no
P1 F5 F6 . . 63.7(8) no
P1 F6 F5 . . 64.2(8) no
C5 O1 C8 . . 105.9(3) no
C1 N1 C2 . . 120.1(4) no
C2 N1 C4 . . 119.4(4) no
C1 N1 C4 . . 120.5(4) no
N1 C1 N1 . 4_555 125.9(4) no
N1 C2 C3 . . 109.6(4) no
C2 C3 C2 . 4_555 111.9(6) no
N1 C4 C5 . . 113.8(3) no
O1 C5 C6 . . 110.2(4) no
C4 C5 C6 . . 133.1(4) no
O1 C5 C4 . . 116.7(4) no
C5 C6 C7 . . 107.4(5) no
C6 C7 C8 . . 107.2(5) no
O1 C8 C9 . . 115.4(5) no
O1 C8 C7 . . 109.2(4) no
C7 C8 C9 . . 135.3(6) no
N1 C1 H1 4_555 . 117.00 no
N1 C1 H1 . . 117.00 no
N1 C2 H2A . . 110.00 no
C3 C2 H2B . . 110.00 no
N1 C2 H2B . . 110.00 no
C3 C2 H2A . . 110.00 no
H2A C2 H2B . . 108.00 no
C2 C3 H3A 4_555 . 109.00 no
C2 C3 H3A . . 109.00 no
C2 C3 H3B . . 109.00 no
H3A C3 H3B . . 108.00 no
C2 C3 H3B 4_555 . 109.00 no
N1 C4 H4B . . 109.00 no
N1 C4 H4A . . 109.00 no
H4A C4 H4B . . 108.00 no
C5 C4 H4A . . 109.00 no
C5 C4 H4B . . 109.00 no
C5 C6 H6 . . 126.00 no
C7 C6 H6 . . 126.00 no
C8 C7 H7 . . 126.00 no
C6 C7 H7 . . 126.00 no
H9B C9 H9C . . 110.00 no
C8 C9 H9A . . 109.00 no
C8 C9 H9B . . 110.00 no
C8 C9 H9C . . 109.00 no
H9A C9 H9B . . 109.00 no
H9A C9 H9C . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 F6 4_555 1.469(11) no
P1 F1 . 1.488(5) no
P1 F2 . 1.510(6) no
P1 F3 . 1.536(6) no
P1 F4 . 1.508(6) no
P1 F5 . 1.474(11) no
P1 F6 . 1.469(11) no
P1 F5 4_555 1.474(11) no
F5 F6 . 1.29(2) no
O1 C5 . 1.372(5) no
O1 C8 . 1.379(6) no
N1 C2 . 1.459(6) no
N1 C4 . 1.474(5) no
N1 C1 . 1.299(4) no
C2 C3 . 1.491(7) no
C4 C5 . 1.467(6) no
C5 C6 . 1.317(7) no
C6 C7 . 1.407(8) no
C7 C8 . 1.334(8) no
C8 C9 . 1.487(8) no
C1 H1 . 0.9300 no
C2 H2B . 0.9700 no
C2 H2A . 0.9700 no
C3 H3A . 0.9700 no
C3 H3B . 0.9700 no
C4 H4A . 0.9700 no
C4 H4B . 0.9700 no
C6 H6 . 0.9300 no
C7 H7 . 0.9300 no
C9 H9C . 0.9600 no
C9 H9A . 0.9600 no
C9 H9B . 0.9600 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 F2 1_554 0.93 2.40 3.312(8) 167 yes
C1 H1 F4 1_454 0.93 2.52 3.044(8) 116 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F5 P1 F5 F6 4_555 . -172.5(11) no
F1 P1 F6 F5 . . -122.5(10) no
F2 P1 F6 F5 . . 142.8(11) no
F1 P1 F5 F6 . . 61.1(11) no
F2 P1 F5 F6 . . -37.4(11) no
F3 P1 F5 F6 . . -117.9(11) no
F4 P1 F5 F6 . . 140.1(11) no
F3 P1 F6 F5 . . 58.6(10) no
F4 P1 F6 F5 . . -39.9(11) no
F6 P1 F6 F5 4_555 . 170.8(12) no
C5 O1 C8 C7 . . 0.9(5) no
C5 O1 C8 C9 . . 178.1(4) no
C8 O1 C5 C4 . . -178.7(4) no
C8 O1 C5 C6 . . 0.2(5) no
C2 N1 C1 N1 . 4_555 -1.9(7) no
C1 N1 C4 C5 . . -121.5(4) no
C4 N1 C1 N1 . 4_555 -180.0(4) no
C2 N1 C4 C5 . . 60.4(5) no
C1 N1 C2 C3 . . -25.1(6) no
C4 N1 C2 C3 . . 153.1(5) no
N1 C2 C3 C2 . 4_555 51.2(7) no
N1 C4 C5 C6 . . 96.4(6) no
N1 C4 C5 O1 . . -85.1(4) no
C4 C5 C6 C7 . . 177.5(5) no
O1 C5 C6 C7 . . -1.1(6) no
C5 C6 C7 C8 . . 1.7(6) no
C6 C7 C8 C9 . . -178.0(6) no
C6 C7 C8 O1 . . -1.6(6) no
