#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/77/2207774.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_2207774
loop_
_publ_author_name
'Chen, Chen'
'Zavalij, Peter Y.'
'Whittingham, M. Stanley'
_publ_section_title
;
 Phosphoric acid imidazolium dihydrogenphosphate
;
_journal_coeditor_code           FL6198
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o258
_journal_page_last               o260
_journal_paper_doi               10.1107/S1600536805041103
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'H3 P O4 , C3 H5 N2 + , H2 P O4 -'
_chemical_formula_moiety         'H3 P O4 , C3 H5 N2 + , H2 P O4 -'
_chemical_formula_sum            'C3 H10 N2 O8 P2'
_chemical_formula_weight         264.07
_chemical_name_common            'imidazolium pentahydrogen diphosphate'
_chemical_name_systematic
'Phosphoric acid imidazolium dihydrogenphosphate'
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 and ZCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 91.447(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.138(4)
_cell_length_b                   14.605(6)
_cell_length_c                   7.516(3)
_cell_measurement_reflns_used    3640
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.6
_cell_volume                     1002.8(7)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6101
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.359
_refine_ls_extinction_coef       0.0192(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.003P)²+1.182P] where P=[-max(Fo²,0)+2Fc²]/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                1895
_reflns_number_total             2291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6198.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207774
_cod_database_fobs_code          2207774
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.1910(4) -0.0147(3) 0.6095(6) 0.0482(12) Uani d PU 0.775(5) A 1 N
H1 0.1425 -0.0293 0.7019 0.058 Uiso calc PR 0.775(5) A 1 H
C2 0.2814(6) 0.0540(3) 0.5987(6) 0.0496(11) Uani d PU 0.775(5) A 1 C
H2 0.3060 0.0947 0.6899 0.059 Uiso calc PR 0.775(5) A 1 H
N3 0.3314(4) 0.0557(3) 0.4369(6) 0.0530(11) Uani d PU 0.775(5) A 1 N
H3 0.3925 0.0948 0.3963 0.064 Uiso calc PR 0.775(5) A 1 H
C4 0.2694(7) -0.0156(5) 0.3435(7) 0.0698(17) Uani d PU 0.775(5) A 1 C
H4 0.2844 -0.0299 0.2248 0.084 Uiso calc PR 0.775(5) A 1 H
C5 0.1858(6) -0.0593(3) 0.4521(8) 0.0580(12) Uani d PU 0.775(5) A 1 C
H5 0.1321 -0.1118 0.4260 0.070 Uiso calc PR 0.775(5) A 1 H
N1A 0.3153(16) 0.0060(13) 0.362(2) 0.0482(12) Uani d P 0.225(5) A 2 N
H1A 0.3587 0.0205 0.2663 0.058 Uiso calc PR 0.225(5) A 2 H
C2A 0.311(2) 0.0571(13) 0.516(4) 0.0580(12) Uani d P 0.225(5) A 2 C
H2A 0.3574 0.1124 0.5406 0.070 Uiso calc PR 0.225(5) A 2 H
N3A 0.226(3) 0.0103(17) 0.617(3) 0.0698(17) Uani d P 0.225(5) A 2 N
H3A 0.2038 0.0251 0.7234 0.084 Uiso calc PR 0.225(5) A 2 H
C4A 0.179(2) -0.0629(15) 0.533(3) 0.0530(11) Uani d P 0.225(5) A 2 C
H4A 0.1091 -0.1034 0.5744 0.064 Uiso calc PR 0.225(5) A 2 H
C5A 0.241(2) -0.0697(12) 0.391(2) 0.0496(11) Uani d P 0.225(5) A 2 C
H5A 0.2357 -0.1201 0.3153 0.059 Uiso calc PR 0.225(5) A 2 H
P1 0.01161(6) 0.16289(3) 0.03493(7) 0.02685(15) Uani d . 1 . . P
O11 0.06306(18) 0.15451(10) -0.15976(19) 0.0386(4) Uani d . 1 . . O
H11 0.0805 0.2056 -0.1990 0.036(9) Uiso calc PR 0.70(4) B 1 H
O12 -0.11891(17) 0.22935(11) 0.0439(2) 0.0476(4) Uani d . 1 . . O
H12 -0.1893 0.2077 -0.0114 0.074(11) Uiso calc R 1 . . H
O13 0.12885(16) 0.20326(11) 0.1534(2) 0.0355(4) Uani d . 1 . . O
H13 0.0916 0.2374 0.2261 0.036(9) Uiso calc PR 0.30(4) B 2 H
O14 -0.03690(19) 0.06759(10) 0.0857(2) 0.0446(4) Uani d . 1 . . O
H14 0.0001 0.0301 0.0192 0.055(17) Uiso calc PR 0.50 . . H
P2 0.50326(6) 0.16567(4) 0.03353(7) 0.02883(15) Uani d . 1 . . P
O21 0.55744(18) 0.15440(11) 0.2303(2) 0.0398(4) Uani d . 1 . . O
H21 0.5776 0.2048 0.2722 0.056(9) Uiso calc R 1 . . H
O22 0.37996(17) 0.23818(11) 0.0257(2) 0.0412(4) Uani d . 1 . . O
H22 0.3072 0.2179 0.0738 0.084(12) Uiso calc R 1 . . H
O23 0.62265(16) 0.20105(11) -0.0815(2) 0.0386(4) Uani d . 1 . . O
O24 0.43963(19) 0.07395(11) -0.0202(2) 0.0475(4) Uani d . 1 . . O
H24 0.5002 0.0336 0.0002 0.056(18) Uiso calc PR 0.50 . . H
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
C2 N1 C5 109.0(3)
C2 N1 H1 125.5
C5 N1 H1 125.5
N1 C2 N3 108.0(3)
N1 C2 H2 126.0
N3 C2 H2 126.0
C2 N3 C4 108.2(3)
C2 N3 H3 125.9
C4 N3 H3 125.9
C5 C4 N3 107.1(4)
C5 C4 H4 126.5
N3 C4 H4 126.5
C4 C5 N1 107.8(4)
C4 C5 H5 126.1
O13 P1 O14 115.00(10)
O13 P1 O12 105.62(9)
O14 P1 O12 109.67(10)
O13 P1 O11 111.24(9)
O14 P1 O11 105.22(9)
O12 P1 O11 110.11(10)
P1 O11 H11 109.5
P1 O12 H12 109.5
P1 O13 H13 109.5
P1 O14 H14 109.5
O23 P2 O24 115.57(10)
O23 P2 O22 106.37(9)
O24 P2 O22 108.77(10)
O23 P2 O21 111.44(9)
O24 P2 O21 105.72(10)
O22 P2 O21 108.82(9)
P2 O21 H21 109.5
P2 O22 H22 109.5
P2 O24 H24 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.303(5) yes
N1 C5 1.351(6) yes
N1 H1 0.8600 ?
C2 N3 1.311(4) yes
C2 H2 0.9300 ?
N3 C4 1.369(6) yes
N3 H3 0.8600 ?
C4 C5 1.299(7) yes
C4 H4 0.9300 ?
C5 H5 0.9300 ?
P1 O13 1.4965(16) yes
P1 O14 1.5125(16) yes
P1 O12 1.5405(16) yes
P1 O11 1.5530(16) yes
P2 O23 1.5010(16) yes
P2 O24 1.5112(17) yes
P2 O22 1.5464(16) yes
P2 O21 1.5565(17) yes
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
N1 H1 O14 3_556 0.86 1.97 2.827(4) 177
N3 H3 O21 . 0.86 2.16 2.986(4) 160
O11 H11 O13 4_565 0.82 1.79 2.587(2) 162
O12 H12 O23 1_455 0.82 1.79 2.554(2) 155
O13 H13 O11 4_566 0.82 1.82 2.587(2) 155
O14 H14 O14 3 0.82 1.67 2.461(3) 162
O21 H21 O23 4_566 0.82 1.80 2.602(2) 165
O22 H22 O13 . 0.82 1.76 2.561(2) 164
O24 H24 O24 3_655 0.82 1.67 2.441(4) 156
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
C5 N1 C2 N3 1.5(5)
N1 C2 N3 C4 -0.3(5)
C2 N3 C4 C5 -1.1(6)
N3 C4 C5 N1 2.0(7)
C2 N1 C5 C4 -2.2(6)
