#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/83/2018378.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_2018378
loop_
_publ_author_name
'Kaman, Ondřej'
'Smrčok, Ľubomír'
'Gyepes, Róbert'
'Havlíček, David'
_publ_section_title
;
 Anilinium dihydrogen phosphate
;
_journal_coeditor_code           LG3072
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o57
_journal_page_last               o60
_journal_paper_doi               10.1107/S0108270111054874
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H8 N + , H2 P O4 -'
_chemical_formula_moiety         'C6 H8 N +, H2 O4 P -'
_chemical_formula_sum            'C6 H10 N O4 P'
_chemical_formula_weight         191.12
_chemical_name_systematic        'anilinium 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           SHELXL97
_cell_angle_alpha                86.418(2)
_cell_angle_beta                 75.8890(19)
_cell_angle_gamma                83.016(2)
_cell_formula_units_Z            6
_cell_length_a                   8.8040(3)
_cell_length_b                   10.4220(4)
_cell_length_c                   14.0890(6)
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      1.00
_cell_volume                     1243.71(8)
_computing_cell_refinement
;
COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997)
;
_computing_data_reduction
;
COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23949
_diffrn_reflns_theta_full        29.24
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.9192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.569
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0508
_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)+(0.0674P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                3848
_reflns_number_total             6720
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lg3072.cif
_cod_data_source_block           I
_cod_database_code               2018378
_cod_database_fobs_code          2018378
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_symmetry_multiplicity
N N21 0.4345(2) 0.34092(16) 0.24020(14) 0.0181(4) Uani d . 1 1
H H21A 0.5187 0.3731 0.1988 0.022 Uiso calc R 1 1
H H21B 0.4212 0.3719 0.3010 0.022 Uiso calc R 1 1
H H21C 0.3464 0.3657 0.2178 0.022 Uiso calc R 1 1
C C24 0.5156(3) -0.0672(2) 0.25426(18) 0.0237(5) Uani d . 1 1
H H24 0.5339 -0.1589 0.2574 0.028 Uiso calc R 1 1
C C23 0.6250(3) 0.0074(2) 0.27262(18) 0.0242(6) Uani d . 1 1
H H23 0.7188 -0.0336 0.2880 0.029 Uiso calc R 1 1
C C26 0.3514(3) 0.1269(2) 0.22638(17) 0.0222(5) Uani d . 1 1
H H26 0.2581 0.1681 0.2105 0.027 Uiso calc R 1 1
C C25 0.3795(3) -0.0067(2) 0.23134(18) 0.0245(6) Uani d . 1 1
H H25 0.3044 -0.0575 0.2189 0.029 Uiso calc R 1 1
C C21 0.4620(3) 0.1992(2) 0.24504(16) 0.0165(5) Uani d . 1 1
C C22 0.5984(3) 0.1416(2) 0.26871(17) 0.0213(5) Uani d . 1 1
H H22 0.6726 0.1927 0.2820 0.026 Uiso calc R 1 1
N N11 0.2303(2) 0.67911(16) 0.07871(14) 0.0227(5) Uani d . 1 1
H H11A 0.2532 0.6444 0.0185 0.027 Uiso calc R 1 1
H H11C 0.1441 0.6463 0.1173 0.027 Uiso calc R 1 1
H H11B 0.3138 0.6592 0.1064 0.027 Uiso calc R 1 1
C C12 0.0596(3) 0.8820(2) 0.12359(18) 0.0215(5) Uani d . 1 1
H H12 -0.0161 0.8336 0.1657 0.026 Uiso calc R 1 1
C C11 0.1978(3) 0.8205(2) 0.06882(17) 0.0185(5) Uani d . 1 1
C C15 0.2807(3) 1.0225(2) -0.00053(18) 0.0257(6) Uani d . 1 1
H H15 0.3561 1.0707 -0.0430 0.031 Uiso calc R 1 1
C C14 0.1429(3) 1.0856(2) 0.05387(18) 0.0239(6) Uani d . 1 1
H H14 0.1237 1.1772 0.0485 0.029 Uiso calc R 1 1
C C13 0.0330(3) 1.0161(2) 0.11607(18) 0.0250(6) Uani d . 1 1
H H13 -0.0612 1.0600 0.1538 0.030 Uiso calc R 1 1
C C16 0.3090(3) 0.8887(2) 0.00678(18) 0.0235(5) Uani d . 1 1
H H16 0.4036 0.8448 -0.0304 0.028 Uiso calc R 1 1
N N31 0.1103(2) 0.32682(16) 0.56741(14) 0.0190(4) Uani d . 1 1
H H31A 0.0221 0.3568 0.5465 0.023 Uiso calc R 1 1
H H31B 0.1953 0.3597 0.5274 0.023 Uiso calc R 1 1
H H31C 0.0992 0.3518 0.6297 0.023 Uiso calc R 1 1
C C31 0.1335(3) 0.18453(19) 0.56522(17) 0.0171(5) Uani d . 1 1
C C32 0.2686(3) 0.1239(2) 0.50684(17) 0.0219(5) Uani d . 1 1
H H32 0.3477 0.1730 0.4689 0.026 Uiso calc R 1 1
C C33 0.2871(3) -0.0100(2) 0.50437(18) 0.0241(6) Uani d . 1 1
H H33 0.3794 -0.0533 0.4642 0.029 Uiso calc R 1 1
C C35 0.0364(3) -0.0179(2) 0.61801(18) 0.0230(5) Uani d . 1 1
H H35 -0.0429 -0.0669 0.6559 0.028 Uiso calc R 1 1
C C36 0.0155(3) 0.1162(2) 0.62099(17) 0.0211(5) Uani d . 1 1
H H36 -0.0773 0.1599 0.6603 0.025 Uiso calc R 1 1
C C34 0.1716(3) -0.0808(2) 0.56031(18) 0.0234(5) Uani d . 1 1
H H34 0.1854 -0.1726 0.5590 0.028 Uiso calc R 1 1
P P2 0.64036(7) 0.58964(5) 0.10131(4) 0.01612(15) Uani d . 1 1
O O8 0.69915(17) 0.44627(13) 0.10256(12) 0.0200(4) Uani d . 1 1
O O7 0.47842(18) 0.62076(15) 0.16555(11) 0.0222(4) Uani d . 1 1
O O6 0.62779(18) 0.64060(15) -0.00346(11) 0.0218(4) Uani d . 1 1
H H6 0.7087 0.6115 -0.0448 0.026 Uiso calc R 1 1
O O5 0.76183(19) 0.66961(14) 0.12767(13) 0.0256(4) Uani d . 1 1
H H5 0.8084 0.6256 0.1662 0.031 Uiso calc R 1 1
P P1 0.01352(7) 0.43251(5) 0.23218(4) 0.01665(15) Uani d . 1 1
O O1 0.04333(18) 0.37131(16) 0.33073(12) 0.0236(4) Uani d . 1 1
H H1 -0.0377 0.3877 0.3759 0.028 Uiso calc R 1 1
O O2 -0.09881(19) 0.34451(14) 0.20354(13) 0.0262(4) Uani d . 1 1
H H2 -0.1517 0.3873 0.1678 0.031 Uiso calc R 1 1
O O4 -0.06423(19) 0.57018(14) 0.24377(12) 0.0249(4) Uani d . 1 1
O O3 0.17167(18) 0.42110(16) 0.16157(12) 0.0259(4) Uani d . 1 1
P P3 0.31410(7) 0.58161(5) 0.43387(4) 0.01555(15) Uani d . 1 1
O O11 0.15413(17) 0.59907(14) 0.50322(11) 0.0202(4) Uani d . 1 1
O O10 0.28992(17) 0.64087(15) 0.33341(11) 0.0217(4) Uani d . 1 1
H H10 0.3749 0.6287 0.2906 0.026 Uiso calc R 1 1
O O12 0.38487(18) 0.44141(14) 0.42566(11) 0.0198(4) Uani d . 1 1
O O9 0.43146(18) 0.66515(14) 0.46195(13) 0.0238(4) Uani d . 1 1
H H9 0.4796 0.6217 0.5000 0.029 Uiso calc R 1 1
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
C21 N21 H21A 109.5
C21 N21 H21B 109.5
H21A N21 H21B 109.5
C21 N21 H21C 109.5
H21A N21 H21C 109.5
H21B N21 H21C 109.5
C25 C24 C23 119.4(2)
C25 C24 H24 120.3
C23 C24 H24 120.3
C22 C23 C24 120.6(2)
C22 C23 H23 119.7
C24 C23 H23 119.7
C21 C26 C25 118.7(2)
C21 C26 H26 120.7
C25 C26 H26 120.7
C24 C25 C26 120.9(2)
C24 C25 H25 119.6
C26 C25 H25 119.6
C22 C21 C26 121.8(2)
C22 C21 N21 118.68(19)
C26 C21 N21 119.5(2)
C21 C22 C23 118.7(2)
C21 C22 H22 120.7
C23 C22 H22 120.7
C11 N11 H11A 109.5
C11 N11 H11C 109.5
H11A N11 H11C 109.5
C11 N11 H11B 109.5
H11A N11 H11B 109.5
H11C N11 H11B 109.5
C11 C12 C13 118.8(2)
C11 C12 H12 120.6
C13 C12 H12 120.6
C12 C11 C16 121.6(2)
C12 C11 N11 119.47(19)
C16 C11 N11 118.9(2)
C14 C15 C16 120.1(2)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C14 C13 120.2(2)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C13 C12 120.2(2)
C14 C13 H13 119.9
C12 C13 H13 119.9
C11 C16 C15 119.0(2)
C11 C16 H16 120.5
C15 C16 H16 120.5
C31 N31 H31A 109.5
C31 N31 H31B 109.5
H31A N31 H31B 109.5
C31 N31 H31C 109.5
H31A N31 H31C 109.5
H31B N31 H31C 109.5
C32 C31 C36 122.1(2)
C32 C31 N31 119.60(19)
C36 C31 N31 118.2(2)
C31 C32 C33 118.8(2)
C31 C32 H32 120.6
C33 C32 H32 120.6
C34 C33 C32 120.2(2)
C34 C33 H33 119.9
C32 C33 H33 119.9
C34 C35 C36 120.5(2)
C34 C35 H35 119.8
C36 C35 H35 119.8
C31 C36 C35 118.3(2)
C31 C36 H36 120.9
C35 C36 H36 120.9
C35 C34 C33 120.0(2)
C35 C34 H34 120.0
C33 C34 H34 120.0
O7 P2 O8 113.31(9)
O7 P2 O5 111.56(10)
O8 P2 O5 109.98(9)
O7 P2 O6 105.17(9)
O8 P2 O6 111.52(9)
O5 P2 O6 104.90(9)
P2 O6 H6 109.5
P2 O5 H5 109.5
O3 P1 O4 113.47(9)
O3 P1 O1 105.27(9)
O4 P1 O1 111.71(10)
O3 P1 O2 111.15(10)
O4 P1 O2 110.25(9)
O1 P1 O2 104.54(9)
P1 O1 H1 109.5
P1 O2 H2 109.5
O11 P3 O12 113.11(9)
O11 P3 O10 105.43(9)
O12 P3 O10 111.58(9)
O11 P3 O9 111.69(9)
O12 P3 O9 109.80(9)
O10 P3 O9 104.87(9)
P3 O10 H10 109.5
P3 O9 H9 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N21 C21 1.468(3) ?
N21 H21A 0.9100 ?
N21 H21B 0.9100 ?
N21 H21C 0.9100 ?
C24 C25 1.384(3) ?
C24 C23 1.389(3) ?
C24 H24 0.9500 ?
C23 C22 1.389(3) ?
C23 H23 0.9500 ?
C26 C21 1.383(3) ?
C26 C25 1.384(3) ?
C26 H26 0.9500 ?
C25 H25 0.9500 ?
C21 C22 1.382(3) ?
C22 H22 0.9500 ?
N11 C11 1.471(3) ?
N11 H11A 0.9100 ?
N11 H11C 0.9100 ?
N11 H11B 0.9100 ?
C12 C11 1.378(3) ?
C12 C13 1.390(3) ?
C12 H12 0.9500 ?
C11 C16 1.379(3) ?
C15 C14 1.381(3) ?
C15 C16 1.388(3) ?
C15 H15 0.9500 ?
C14 C13 1.381(3) ?
C14 H14 0.9500 ?
C13 H13 0.9500 ?
C16 H16 0.9500 ?
N31 C31 1.473(3) ?
N31 H31A 0.9100 ?
N31 H31B 0.9100 ?
N31 H31C 0.9100 ?
C31 C32 1.377(3) ?
C31 C36 1.384(3) ?
C32 C33 1.387(3) ?
C32 H32 0.9500 ?
C33 C34 1.385(3) ?
C33 H33 0.9500 ?
C35 C34 1.383(3) ?
C35 C36 1.390(3) ?
C35 H35 0.9500 ?
C36 H36 0.9500 ?
C34 H34 0.9500 ?
P1 O1 1.5588(16) y
P1 O2 1.5631(16) y
P1 O3 1.4972(16) y
P1 O4 1.5133(16) y
P2 O5 1.5574(15) y
P2 O6 1.5623(16) y
P2 O7 1.5007(16) y
P2 O8 1.5211(15) y
O6 H6 0.8400 ?
O5 H5 0.8400 ?
O1 H1 0.8400 ?
O2 H2 0.8400 ?
P3 O9 1.5632(15) y
P3 O10 1.5607(16) y
P3 O11 1.5034(16) y
P3 O12 1.5169(15) y
O10 H10 0.8400 ?
O9 H9 0.8400 ?
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
C25 C24 C23 C22 0.4(4)
C23 C24 C25 C26 0.1(4)
C21 C26 C25 C24 -0.2(3)
C25 C26 C21 C22 -0.3(3)
C25 C26 C21 N21 -180.0(2)
C26 C21 C22 C23 0.7(3)
N21 C21 C22 C23 -179.6(2)
C24 C23 C22 C21 -0.8(3)
C13 C12 C11 C16 -0.3(3)
C13 C12 C11 N11 177.8(2)
C16 C15 C14 C13 0.2(4)
C15 C14 C13 C12 -0.6(4)
C11 C12 C13 C14 0.7(3)
C12 C11 C16 C15 -0.1(3)
N11 C11 C16 C15 -178.1(2)
C14 C15 C16 C11 0.1(3)
C36 C31 C32 C33 -0.3(3)
N31 C31 C32 C33 -178.9(2)
C31 C32 C33 C34 -0.4(3)
C32 C31 C36 C35 0.6(3)
N31 C31 C36 C35 179.2(2)
C34 C35 C36 C31 -0.2(3)
C36 C35 C34 C33 -0.5(4)
C32 C33 C34 C35 0.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 148639
2 PubChem 139061251
