#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223527.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_2223527
loop_
_publ_author_name
'Zhang, Li'
_publ_section_title
;
 2-Cyanoanilinium dihydrogen phosphate
;
_journal_coeditor_code           PV2201
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2449
_journal_paper_doi               10.1107/S1600536809034898
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H7 N2 +, H2 P O4 -'
_chemical_formula_moiety         'C7 H7 N2 +, H2 O4 P -'
_chemical_formula_sum            'C7 H9 N2 O4 P'
_chemical_formula_weight         216.13
_chemical_name_systematic
;
2-Cyanoanilinium dihydrogen phosphate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.20(2)
_cell_angle_beta                 93.75(2)
_cell_angle_gamma                99.61(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1471(12)
_cell_length_b                   9.3192(19)
_cell_length_c                   9.3295(19)
_cell_measurement_reflns_used    1852
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.41
_cell_volume                     462.52(19)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       'CCD profile fitting'
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4831
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.372
_refine_ls_extinction_coef       0.126(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0401
_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)+(0.0436P)²+0.23P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                1852
_reflns_number_total             2110
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2201.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        462.51(16)
_cod_database_code               2223527
_cod_database_fobs_code          2223527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.3606(3) 0.17867(19) 0.13975(19) 0.0252(3) Uani d . 1 . .
H H1A 0.4996 0.1956 0.1197 0.038 Uiso calc R 1 . .
H H1B 0.2813 0.2336 0.1078 0.038 Uiso calc R 1 . .
H H1C 0.2980 0.0710 0.0852 0.038 Uiso calc R 1 . .
C C2 0.5068(3) 0.1896(2) 0.3985(2) 0.0275(4) Uani d . 1 . .
C C1 0.3654(3) 0.2371(2) 0.3135(2) 0.0254(4) Uani d . 1 . .
N N2 0.7647(4) -0.0074(3) 0.2631(3) 0.0524(6) Uani d . 1 . .
C C7 0.6495(4) 0.0801(3) 0.3194(3) 0.0343(5) Uani d . 1 . .
C C3 0.5080(4) 0.2455(3) 0.5646(3) 0.0381(5) Uani d . 1 . .
H H3 0.6040 0.2152 0.6217 0.046 Uiso calc R 1 . .
C C6 0.2255(4) 0.3362(3) 0.3937(3) 0.0406(5) Uani d . 1 . .
H H6 0.1296 0.3674 0.3374 0.049 Uiso calc R 1 . .
C C5 0.2268(5) 0.3900(3) 0.5589(3) 0.0524(7) Uani d . 1 . .
H H5 0.1312 0.4571 0.6128 0.063 Uiso calc R 1 . .
C C4 0.3683(5) 0.3452(3) 0.6444(3) 0.0479(6) Uani d . 1 . .
H H4 0.3687 0.3824 0.7554 0.057 Uiso calc R 1 . .
P P1 0.87212(8) 0.26924(6) 0.96817(6) 0.02198(17) Uani d . 1 . .
O O4 1.1050(2) 0.36166(16) 1.05571(18) 0.0311(3) Uani d . 1 . .
O O3 0.8776(2) 0.16546(19) 0.77991(17) 0.0371(4) Uani d . 1 . .
H H3A 0.9862 0.1229 0.7672 0.056 Uiso calc R 1 . .
O O2 0.7151(2) 0.38600(16) 0.97509(17) 0.0294(3) Uani d . 1 . .
H H2A 0.7833 0.4620 0.9628 0.044 Uiso calc R 1 . .
O O1 0.7610(2) 0.15769(17) 1.02994(18) 0.0334(4) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0267(8) 0.0251(8) 0.0264(8) 0.0079(6) 0.0025(6) 0.0141(6)
C2 0.0282(10) 0.0272(9) 0.0308(10) 0.0111(8) 0.0046(8) 0.0151(8)
C1 0.0274(10) 0.0233(9) 0.0269(10) 0.0076(7) 0.0031(7) 0.0128(8)
N2 0.0607(14) 0.0626(14) 0.0557(13) 0.0420(12) 0.0216(11) 0.0354(11)
C7 0.0382(11) 0.0409(12) 0.0354(11) 0.0170(10) 0.0054(9) 0.0252(10)
C3 0.0446(13) 0.0445(12) 0.0315(11) 0.0167(10) 0.0029(9) 0.0216(10)
C6 0.0442(13) 0.0484(13) 0.0360(12) 0.0294(11) 0.0081(10) 0.0192(10)
C5 0.0595(16) 0.0646(16) 0.0396(13) 0.0418(14) 0.0199(12) 0.0194(12)
C4 0.0612(16) 0.0555(15) 0.0277(11) 0.0264(13) 0.0098(10) 0.0156(10)
P1 0.0221(3) 0.0226(3) 0.0254(3) 0.00653(18) 0.00367(18) 0.0144(2)
O4 0.0277(7) 0.0282(7) 0.0405(8) 0.0032(6) -0.0050(6) 0.0213(6)
O3 0.0372(8) 0.0480(9) 0.0272(8) 0.0222(7) 0.0062(6) 0.0144(7)
O2 0.0253(7) 0.0276(7) 0.0427(8) 0.0101(5) 0.0087(6) 0.0211(6)
O1 0.0370(8) 0.0290(7) 0.0422(9) 0.0056(6) 0.0087(6) 0.0238(7)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 H1A . . 109.5 ?
C1 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C1 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C3 C2 C1 . . 119.88(18) ?
C3 C2 C7 . . 118.03(18) ?
C1 C2 C7 . . 122.07(18) ?
C6 C1 C2 . . 119.67(19) ?
C6 C1 N1 . . 119.67(17) ?
C2 C1 N1 . . 120.64(16) ?
N2 C7 C2 . . 176.7(2) ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C1 C6 C5 . . 119.9(2) ?
C1 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
O1 P1 O4 . . 113.96(8) ?
O1 P1 O2 . . 107.38(8) ?
O4 P1 O2 . . 112.70(8) ?
O1 P1 O3 . . 109.65(9) ?
O4 P1 O3 . . 109.18(9) ?
O2 P1 O3 . . 103.43(8) ?
P1 O3 H3A . . 109.5 ?
P1 O2 H2A . . 109.5 ?
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
N1 C1 . 1.452(2) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C2 C3 . 1.390(3) ?
C2 C1 . 1.393(3) ?
C2 C7 . 1.431(3) ?
C1 C6 . 1.368(3) ?
N2 C7 . 1.137(3) ?
C3 C4 . 1.368(3) ?
C3 H3 . 0.9300 ?
C6 C5 . 1.384(3) ?
C6 H6 . 0.9300 ?
C5 C4 . 1.379(4) ?
C5 H5 . 0.9300 ?
C4 H4 . 0.9300 ?
P1 O1 . 1.4972(14) ?
P1 O4 . 1.5004(15) ?
P1 O2 . 1.5537(14) ?
P1 O3 . 1.5770(15) ?
O3 H3A . 0.8200 ?
O2 H2A . 0.8200 ?
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 H1B O4 1_454 0.89 1.93 2.819(2) 175.5
N1 H1C O1 2_656 0.89 1.85 2.723(2) 166.1
N1 H1A O1 1_554 0.89 1.87 2.730(2) 161.3
O3 H3A N2 2_756 0.82 1.98 2.797(2) 176.1
O2 H2A O4 2_767 0.82 1.76 2.574(2) 171.5
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 C2 C1 C6 . . . . -1.2(3) ?
C7 C2 C1 C6 . . . . 177.2(2) ?
C3 C2 C1 N1 . . . . -179.47(18) ?
C7 C2 C1 N1 . . . . -1.1(3) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C7 C2 C3 C4 . . . . -177.5(2) ?
C2 C1 C6 C5 . . . . 0.6(4) ?
N1 C1 C6 C5 . . . . 178.9(2) ?
C1 C6 C5 C4 . . . . 0.2(4) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C6 C5 C4 C3 . . . . -0.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655897
