##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 980665'
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Diethylammonium dihydrogen orthophosphate
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C4 H12 N +, H2 O4 P -'
_chemical_formula_sum     'C4 H14 N O4 P'
_chemical_formula_structural     '[(N H2 (C H2 C H3)2) (H2 P O4)]'
_chemical_formula_iupac     'C4 H12 N +, H2 P O4 -'
_chemical_formula_weight     171.13
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.3643(6)
_cell_length_b     8.8308(15)
_cell_length_c     11.6446(12)
_cell_angle_alpha     88.219(10)
_cell_angle_beta     83.649(7)
_cell_angle_gamma     79.700(7)
_cell_volume     841.00(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     20.98
_cell_measurement_theta_max     25.96
_cell_measurement_temperature     295(2)
_exptl_crystal_description     parallelepiped
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     368
_exptl_absorpt_coefficient_mu     0.292
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.8584
_exptl_absorpt_correction_T_max     0.9975
_exptl_special_details
;
A suitable single-crystal was carefully selected under a polarizing microscope
and mounted in a glass capillary.
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius MACH3'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     10831
_diffrn_reflns_av_R_equivalents     0.0373
_diffrn_reflns_av_sigmaI/netI     0.0507
_diffrn_reflns_theta_min     2.49
_diffrn_reflns_theta_max     30.43
_diffrn_reflns_theta_full     30.43
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     -6.30
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     5096
_reflns_number_gt     3164
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0875
_refine_ls_R_factor_gt     0.0398
_refine_ls_wR_factor_gt     0.0986
_refine_ls_wR_factor_ref     0.1186
_refine_ls_goodness_of_fit_ref     0.984
_refine_ls_restrained_S_all     0.984
_refine_ls_number_reflns     5096
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0553P)²+0.1855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.373
_refine_diff_density_min     -0.386
_refine_ls_extinction_method     none
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'
_computing_data_collection     'CAD-4 (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 (Enraf--Nonius, 1989)'
_computing_data_reduction     'WINGX (Farrugia, 2012)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ATOMS (Dowty, 2002) and ORTEP-3 for Windows (Farrugia, 2012)'
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.16567(5) 0.37327(5) 0.60452(4) 0.02736(12) Uani d . 1 1 . .
    O O11 0.33132(15) 0.27994(16) 0.61779(12) 0.0362(3) Uani d . 1 1 . .
    O O12 0.16402(16) 0.53915(15) 0.56977(12) 0.0365(3) Uani d . 1 1 . .
    O O13 0.05039(16) 0.36883(18) 0.71998(12) 0.0426(4) Uani d . 1 1 . .
    H H13 0.0986 0.3119 0.7669 0.064 Uiso calc R 1 1 . .
    O O14 0.08747(18) 0.29249(16) 0.51243(13) 0.0418(3) Uani d . 1 1 . .
    H H14 -0.0034 0.3416 0.5037 0.063 Uiso calc R 1 1 . .
    P P2 0.67897(6) -0.09624(6) 0.11311(4) 0.03332(13) Uani d . 1 1 . .
    O O21 0.83801(17) -0.20760(18) 0.10779(12) 0.0431(4) Uani d . 1 1 . .
    O O22 0.68455(18) 0.04631(17) 0.03943(13) 0.0454(4) Uani d . 1 1 . .
    O O23 0.6256(2) -0.04343(17) 0.24046(13) 0.0502(4) Uani d . 1 1 . .
    H H23 0.6138 -0.1185 0.2816 0.075 Uiso calc R 1 1 . .
    O O24 0.54703(19) -0.18437(17) 0.07620(15) 0.0540(4) Uani d . 1 1 . .
    H H24 0.4588 -0.1259 0.0784 0.081 Uiso calc R 1 1 . .
    C C11 0.2499(4) 0.5728(3) -0.0009(3) 0.0663(7) Uani d . 1 1 . .
    H H11A 0.3010 0.4677 -0.0143 0.100 Uiso calc R 1 1 . .
    H H11B 0.1790 0.5792 0.0702 0.100 Uiso calc R 1 1 . .
    H H11C 0.3322 0.6346 0.0040 0.100 Uiso calc R 1 1 . .
    C C12 0.1521(3) 0.6303(3) -0.0985(2) 0.0551(6) Uani d . 1 1 . .
    H H12A 0.2234 0.6223 -0.1705 0.066 Uiso calc R 1 1 . .
    H H12B 0.0700 0.5668 -0.1043 0.066 Uiso calc R 1 1 . .
    N N1 0.0712(2) 0.7927(2) -0.08051(14) 0.0389(4) Uani d . 1 1 . .
    H H1A 0.1462 0.8472 -0.0629 0.047 Uiso calc R 1 1 . .
    H H1B -0.0049 0.7962 -0.0192 0.047 Uiso calc R 1 1 . .
    C C13 -0.0092(4) 0.8696(3) -0.1815(2) 0.0633(7) Uani d . 1 1 . .
    H H13A -0.0518 0.9767 -0.1634 0.076 Uiso calc R 1 1 . .
    H H13B 0.0719 0.8668 -0.2481 0.076 Uiso calc R 1 1 . .
    C C14 -0.1460(4) 0.7938(4) -0.2114(2) 0.0674(8) Uani d . 1 1 . .
    H H14A -0.1939 0.8467 -0.2759 0.101 Uiso calc R 1 1 . .
    H H14B -0.2275 0.7978 -0.1461 0.101 Uiso calc R 1 1 . .
    H H14C -0.1040 0.6884 -0.2311 0.101 Uiso calc R 1 1 . .
    C C21 0.2697(4) 0.9059(3) 0.4832(3) 0.0767(9) Uani d . 1 1 . .
    H H21A 0.2125 1.0088 0.4722 0.115 Uiso calc R 1 1 . .
    H H21B 0.3793 0.9091 0.4988 0.115 Uiso calc R 1 1 . .
    H H21C 0.2144 0.8581 0.5472 0.115 Uiso calc R 1 1 . .
    C C22 0.2739(3) 0.8160(3) 0.3772(2) 0.0530(6) Uani d . 1 1 . .
    H H22A 0.3283 0.8650 0.3122 0.064 Uiso calc R 1 1 . .
    H H22B 0.1632 0.8138 0.3608 0.064 Uiso calc R 1 1 . .
    N N2 0.36206(19) 0.65586(19) 0.39194(14) 0.0387(4) Uani d . 1 1 . .
    H H2A 0.4643 0.6596 0.4076 0.046 Uiso calc R 1 1 . .
    H H2B 0.3118 0.6126 0.4535 0.046 Uiso calc R 1 1 . .
    C C23 0.3717(3) 0.5556(3) 0.2904(2) 0.0524(6) Uani d . 1 1 . .
    H H23A 0.4293 0.5993 0.2242 0.063 Uiso calc R 1 1 . .
    H H23B 0.2622 0.5520 0.2721 0.063 Uiso calc R 1 1 . .
    C C24 0.4584(3) 0.3952(3) 0.3128(2) 0.0599(7) Uani d . 1 1 . .
    H H24A 0.4627 0.3337 0.2456 0.090 Uiso calc R 1 1 . .
    H H24B 0.4005 0.3509 0.3773 0.090 Uiso calc R 1 1 . .
    H H24C 0.5675 0.3983 0.3297 0.090 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 O11 . 1.5013(13) ?
    P1 O12 . 1.5056(14) ?
    P1 O14 . 1.5673(14) ?
    P1 O13 . 1.5691(14) ?
    O13 H13 . 0.8200 ?
    O14 H14 . 0.8200 ?
    P2 O21 . 1.5027(14) ?
    P2 O22 . 1.5060(14) ?
    P2 O23 . 1.5613(16) ?
    P2 O24 . 1.5624(15) ?
    O23 H23 . 0.8200 ?
    O24 H24 . 0.8200 ?
    C11 C12 . 1.497(4) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 N1 . 1.483(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    N1 C13 . 1.503(3) ?
    N1 H1A . 0.9000 ?
    N1 H1B . 0.9000 ?
    C13 C14 . 1.501(4) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C21 C22 . 1.482(4) ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C22 N2 . 1.487(3) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    N2 C23 . 1.485(3) ?
    N2 H2A . 0.9000 ?
    N2 H2B . 0.9000 ?
    C23 C24 . 1.501(4) ?
    C23 H23A . 0.9700 ?
    C23 H23B . 0.9700 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 0.9600 ?
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
    O11 P1 O12 . . 115.38(8) ?
    O11 P1 O14 . . 107.71(8) ?
    O12 P1 O14 . . 109.31(8) ?
    O11 P1 O13 . . 110.08(7) ?
    O12 P1 O13 . . 108.20(8) ?
    O14 P1 O13 . . 105.74(9) ?
    P1 O13 H13 . . 109.5 ?
    P1 O14 H14 . . 109.5 ?
    O21 P2 O22 . . 114.38(9) ?
    O21 P2 O23 . . 109.41(8) ?
    O22 P2 O23 . . 107.50(9) ?
    O21 P2 O24 . . 107.55(9) ?
    O22 P2 O24 . . 110.16(8) ?
    O23 P2 O24 . . 107.65(10) ?
    P2 O23 H23 . . 109.5 ?
    P2 O24 H24 . . 109.5 ?
    C12 C11 H11A . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C12 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N1 C12 C11 . . 110.87(19) ?
    N1 C12 H12A . . 109.5 ?
    C11 C12 H12A . . 109.5 ?
    N1 C12 H12B . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C12 N1 C13 . . 115.31(19) ?
    C12 N1 H1A . . 108.4 ?
    C13 N1 H1A . . 108.4 ?
    C12 N1 H1B . . 108.4 ?
    C13 N1 H1B . . 108.4 ?
    H1A N1 H1B . . 107.5 ?
    C14 C13 N1 . . 112.3(2) ?
    C14 C13 H13A . . 109.1 ?
    N1 C13 H13A . . 109.1 ?
    C14 C13 H13B . . 109.1 ?
    N1 C13 H13B . . 109.1 ?
    H13A C13 H13B . . 107.9 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C22 C21 H21A . . 109.5 ?
    C22 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C22 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C21 C22 N2 . . 110.6(2) ?
    C21 C22 H22A . . 109.5 ?
    N2 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    N2 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 108.1 ?
    C23 N2 C22 . . 114.70(18) ?
    C23 N2 H2A . . 108.6 ?
    C22 N2 H2A . . 108.6 ?
    C23 N2 H2B . . 108.6 ?
    C22 N2 H2B . . 108.6 ?
    H2A N2 H2B . . 107.6 ?
    N2 C23 C24 . . 111.64(19) ?
    N2 C23 H23A . . 109.3 ?
    C24 C23 H23A . . 109.3 ?
    N2 C23 H23B . . 109.3 ?
    C24 C23 H23B . . 109.3 ?
    H23A C23 H23B . . 108.0 ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
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
    O13 H13 O21 2_656 0.82 1.78 2.5851(19) 166.2
    O14 H14 O12 2_566 0.82 1.83 2.6058(19) 158.0
    O24 H24 O22 2_655 0.82 1.95 2.585(2) 133.2
    O23 H23 O11 2_656 0.82 1.84 2.620(2) 157.8
    N1 H1A O22 2_665 0.90 1.88 2.779(2) 174.4
    N1 H1B O21 1_465 0.90 1.87 2.769(2) 177.0
    N2 H2A O11 2_666 0.90 1.87 2.714(2) 155.0
    N2 H2B O12 . 0.90 1.91 2.795(2) 167.8
data_global
_journal_date_recd_electronic     2013-12-09
_journal_date_accepted     2014-01-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      2
_journal_page_first     o129
_journal_page_last     o129
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814000464
_journal_coeditor_code     WM2794
_publ_contact_author_name     'Dr P. Held'
_publ_contact_author_address
;
  Institut für Kristallographie
  Universität zu Köln
  Greinstrasse 6
  D-50939 Köln
  Germany
;
_publ_contact_author_email     peter.held@uni-koeln.de
_publ_contact_author_fax     '49-221-470-4963'
_publ_contact_author_phone     '49-221-470-6103'
_publ_section_title
;
Diethylammonium dihydrogen orthophosphate
;
loop_
    _publ_author_name
    _publ_author_address
    'Held, Peter'
; Institut für Kristallographie
  Universität zu Köln
  Greinstrasse 6
  D-50939 Köln
  Germany
;
