#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/83/1508370.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_1508370
loop_
_publ_author_name
'Harrison, William T. A.'
_publ_section_title
;
 Supramolecular Hydrogen-Bond Motifs in Chiral and Racemic Molecular
 Salts: A Comparison of (S)-2-Methyl Piperizinium Hydrogen Phosphite
 Monohydrate, C5H14N2·HPO3·H2O and (R,S)-2-Methyl
 Piperizinium Hydrogen Phosphite 2.23 Hydrate,
 C5H14N2·HPO3·2.23H2O
;
_journal_issue                   4
_journal_name_full               Crystals
_journal_page_first              236
_journal_page_last               243
_journal_paper_doi               10.3390/cryst1040236
_journal_volume                  1
_journal_year                    2011
_chemical_formula_moiety         'C5 H14 N2, H O3 P, 2.230(H2 O)'
_chemical_formula_sum            'C5 H19.47 N2 O5.24 P'
_chemical_formula_weight         222.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   31.075(2)
_cell_length_b                   31.075(2)
_cell_length_c                   6.1875(4)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.42
_cell_measurement_theta_min      2.27
_cell_volume                     5174.5(6)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART1000 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  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11694
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2167
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                1419
_reflns_number_total             2270
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file
C5H19.47N2O5.24P_crystals-01-00236-s001_R_3_DC114.cif
_cod_data_source_block           wh415a_chateigner
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1508370
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
C1 C 0.16424(10) 0.13329(10) 1.0671(4) 0.0488(7) Uani 1 1 d .
H1A H 0.1521 0.1460 1.1806 0.059 Uiso 1 1 calc R
H1B H 0.1426 0.0975 1.0599 0.059 Uiso 1 1 calc R
C2 C 0.16336(10) 0.15629(10) 0.8542(4) 0.0472(7) Uani 1 1 d .
H2A H 0.1732 0.1418 0.7393 0.057 Uiso 1 1 calc R
H2B H 0.1299 0.1494 0.8241 0.057 Uiso 1 1 calc R
C3 C 0.24875(9) 0.22250(10) 0.9113(4) 0.0430(7) Uani 1 1 d .
H3A H 0.2700 0.2583 0.9195 0.052 Uiso 1 1 calc R
H3B H 0.2611 0.2104 0.7958 0.052 Uiso 1 1 calc R
C4 C 0.25143(9) 0.19952(9) 1.1228(4) 0.0388(6) Uani 1 1 d .
H4 H 0.2419 0.2143 1.2400 0.047 Uiso 1 1 calc R
C5 C 0.30388(11) 0.20969(12) 1.1653(5) 0.0648(9) Uani 1 1 d .
H5A H 0.3047 0.1948 1.3000 0.097 Uiso 1 1 calc R
H5B H 0.3262 0.2449 1.1722 0.097 Uiso 1 1 calc R
H5C H 0.3139 0.1958 1.0505 0.097 Uiso 1 1 calc R
N1 N 0.19754(7) 0.21057(8) 0.8604(3) 0.0394(5) Uani 1 1 d .
H1C H 0.1972 0.2238 0.7314 0.047 Uiso 1 1 calc R
H1D H 0.1871 0.2242 0.9609 0.047 Uiso 1 1 calc R
N2 N 0.21563(8) 0.14508(7) 1.1178(3) 0.0404(5) Uani 1 1 d .
H2C H 0.2256 0.1309 1.0179 0.048 Uiso 1 1 calc R
H2D H 0.2158 0.1319 1.2472 0.048 Uiso 1 1 calc R
P1 P 0.15266(2) 0.24525(3) 0.38144(10) 0.0360(2) Uani 1 1 d .
H1 H 0.1582 0.2896 0.4167 0.043 Uiso 1 1 calc R
O1 O 0.14844(6) 0.23776(7) 0.1386(2) 0.0463(5) Uani 1 1 d .
O2 O 0.10577(6) 0.20855(7) 0.4993(3) 0.0542(5) Uani 1 1 d .
O3 O 0.19835(6) 0.24666(7) 0.4717(3) 0.0503(5) Uani 1 1 d .
O4 O 0.29532(8) 0.31123(7) 0.3594(3) 0.0701(6) Uani 1 1 d .
H41 H 0.2634 0.2900 0.4100 0.084 Uiso 1 1 d R
H42 H 0.3127 0.3114 0.4799 0.084 Uiso 1 1 d R
O5 O 0.05851(10) 0.10381(10) 0.4680(6) 0.1335(13) Uani 1 1 d .
H51 H 0.0813 0.1396 0.4829 0.160 Uiso 1 1 d R
H52 H 0.0280 0.0981 0.4446 0.160 Uiso 1 1 d R
O6 O 0.06189(10) 0.02022(10) -0.0346(6) 0.239(15) Uiso 0.230(11) 1 d PR
H61 H 0.0748 0.0280 -0.1687 0.287 Uiso 0.230(11) 1 d PR
H62 H 0.0368 0.0268 -0.0347 0.287 Uiso 0.230(11) 1 d PR
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 109.9(2) . . ?
N2 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N2 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C1 110.2(2) . . ?
N1 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C4 111.9(2) . . ?
N1 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 C3 109.4(2) . . ?
N2 C4 C5 110.7(2) . . ?
C3 C4 C5 111.0(2) . . ?
N2 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 N1 C2 111.20(19) . . ?
C3 N1 H1C 109.4 . . ?
C2 N1 H1C 109.4 . . ?
C3 N1 H1D 109.4 . . ?
C2 N1 H1D 109.4 . . ?
H1C N1 H1D 108.0 . . ?
C1 N2 C4 112.68(19) . . ?
C1 N2 H2C 109.1 . . ?
C4 N2 H2C 109.1 . . ?
C1 N2 H2D 109.1 . . ?
C4 N2 H2D 109.1 . . ?
H2C N2 H2D 107.8 . . ?
O3 P1 O2 112.43(10) . . y
O3 P1 O1 112.34(10) . . y
O2 P1 O1 112.62(10) . . y
O3 P1 H1 106.3 . . ?
O2 P1 H1 106.3 . . ?
O1 P1 H1 106.3 . . ?
H41 O4 H42 98.5 . . ?
H51 O5 H52 109.8 . . ?
O6 O6 O6 114.22(18) 11 12 ?
O6 O6 H61 120.5 11 . ?
O6 O6 H61 107.6 12 . ?
O6 O6 H62 90.1 11 . ?
O6 O6 H62 32.8 12 . ?
H61 O6 H62 105.0 . . ?
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
C1 N2 1.483(3) . ?
C1 C2 1.506(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.478(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.476(3) . ?
C3 C4 1.513(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.489(3) . ?
C4 C5 1.520(4) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
N2 H2C 0.9000 . ?
N2 H2D 0.9000 . ?
P1 O3 1.5059(18) . y
P1 O2 1.5144(18) . y
P1 O1 1.5161(16) . y
P1 H1 1.3200 . ?
O4 H41 0.9283 . ?
O4 H42 0.9188 . ?
O5 H51 0.9781 . ?
O5 H52 0.8854 . ?
O6 O6 1.752(3) 11 ?
O6 O6 1.752(3) 12 ?
O6 H61 0.9006 . ?
O6 H62 0.8993 . ?
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 H1C O3 0.90 1.75 2.648(3) 176 .
N1 H1D O1 0.90 1.83 2.701(3) 164 1_556
N2 H2C O1 0.90 1.80 2.680(3) 166 11_556
N2 H2D O2 0.90 1.77 2.665(3) 173 11_557
O4 H41 O3 0.93 1.82 2.746(3) 172 .
O4 H42 O4 0.92 1.81 2.724(2) 171 5
O5 H51 O2 0.98 1.89 2.830(3) 161 .
O5 H52 O5 0.89 2.05 2.829(3) 147 12_556
O6 H61 O5 0.90 2.01 2.912(7) 180 11
O6 H62 O6 0.90 2.04 2.942(5) 180 2
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
N2 C1 C2 N1 -57.3(3)
N1 C3 C4 N2 54.1(3)
N1 C3 C4 C5 176.6(2)
C4 C3 N1 C2 -56.8(3)
C1 C2 N1 C3 57.8(3)
C2 C1 N2 C4 57.0(3)
C3 C4 N2 C1 -54.8(3)
C5 C4 N2 C1 -177.5(2)
