#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/79/2007900.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_2007900
loop_
_publ_author_name
'Trojette, Basma'
'Hajem, Amen Allah'
'Driss, Ahmed'
'Jouini, Tahar'
_publ_section_title
;
 Monoprotonated o-Phenylenediamine Dihydrogenphosphate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1867
_journal_page_last               1869
_journal_paper_doi               10.1107/S0108270198009147
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C6 H9 N2 1+ , H2 P O4 1-'
_chemical_formula_structural     '(1,2 NH3C6H4NH2)H2PO4'
_chemical_formula_sum            'C6 H11 N2 O4 P'
_chemical_formula_weight         206.14
_chemical_name_systematic
;
Monoprotonated-Orthophenylenediamine Dihydrogenphosphate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                91.30(2)
_cell_angle_beta                 95.16(2)
_cell_angle_gamma                100.71(2)
_cell_formula_units_Z            2
_cell_length_a                   4.556(2)
_cell_length_b                   9.689(2)
_cell_length_c                   10.752(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17
_cell_measurement_theta_min      6
_cell_volume                     464.1(2)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection
'CAD-4 EXPRESS (Duisenberg, 1992; Macicek & Yordanov, 1992)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'CAD4 diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1865
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9997
_exptl_absorpt_correction_T_min  0.9352
_exptl_absorpt_correction_type   'empirical psi-scan (North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.289
_refine_ls_extinction_coef       0.019(6)
_refine_ls_extinction_method     SHELXL93_(Sheldrick,_1993)
_refine_ls_goodness_of_fit_all   1.092
_refine_ls_goodness_of_fit_obs   1.104
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_restrained_S_obs      1.104
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_obs          0.0320
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0476P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0910
_refine_ls_wR_factor_obs         0.0831
_reflns_number_observed          1366
_reflns_number_total             1639
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            cf1225.cif
_cod_data_source_block           psi2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2007900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P1 0.0204(3) 0.0247(3) 0.0310(3) 0.0027(2) -0.0018(2) -0.0010(2)
O1 0.0303(7) 0.0424(8) 0.0324(8) 0.0074(6) -0.0019(6) -0.0020(6)
O2 0.0244(7) 0.0253(7) 0.0561(9) 0.0038(6) -0.0045(6) 0.0041(6)
O3 0.0335(8) 0.0245(8) 0.0750(12) 0.0034(7) -0.0047(8) -0.0081(7)
O4 0.0229(8) 0.0934(14) 0.0326(9) 0.0036(8) -0.0011(7) -0.0029(8)
N1 0.0284(9) 0.0235(9) 0.0306(9) 0.0032(7) -0.0021(8) -0.0008(7)
N2 0.0374(10) 0.0237(9) 0.0528(12) -0.0001(8) -0.0059(9) 0.0050(8)
C1 0.0350(10) 0.0270(10) 0.0290(10) 0.010(8) -0.001(8) 0.001(7)
C2 0.0360(10) 0.0270(10) 0.0380(10) 0.0110(10) 0.0040(10) 0.0030(10)
C3 0.071(2) 0.0400(10) 0.050(2) 0.0130(10) 0.0110(10) 0.0160(10)
C4 0.111(3) 0.064(2) 0.0340(10) 0.031(2) 0.0010(10) 0.0130(10)
C5 0.105(2) 0.058(2) 0.0350(10) 0.020(2) -0.021(2) -0.0080(10)
C6 0.070(2) 0.0350(10) 0.0390(10) 0.0080(10) -0.0140(10) -0.0040(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
P1 0.20611(10) 0.25703(5) 0.37298(4) 0.0259(2) Uani d . 1 . P
O1 0.3632(3) 0.2836(2) 0.50230(10) 0.0353(4) Uani d . 1 . O
O2 -0.0208(3) 0.34890(10) 0.34360(10) 0.0359(4) Uani d . 1 . O
O3 0.0237(4) 0.1023(2) 0.3566(2) 0.0454(4) Uani d . 1 . O
O4 0.4318(4) 0.2689(2) 0.2728(2) 0.0509(5) Uani d . 1 . O
N1 -0.0794(4) 0.3642(2) 0.6387(2) 0.0280(4) Uani d . 1 . N
N2 -0.4012(4) 0.0838(2) 0.6727(2) 0.0393(5) Uani d . 1 . N
C1 -0.0814(4) 0.3025(2) 0.7611(2) 0.0299(4) Uani d . 1 . C
C2 -0.2465(5) 0.1688(2) 0.7755(2) 0.0331(5) Uani d . 1 . C
C3 -0.2347(7) 0.1153(3) 0.8946(2) 0.0528(7) Uani d . 1 . C
C4 -0.0649(8) 0.1915(3) 0.9937(2) 0.0677(9) Uani d . 1 . C
C5 0.0989(8) 0.3227(3) 0.9780(2) 0.0671(9) Uani d . 1 . C
C6 0.0909(6) 0.3786(3) 0.8611(2) 0.0495(6) Uani d . 1 . C
HO3 0.128(8) 0.049(3) 0.358(3) 0.072(10) Uiso d . 1 . H
HO4 0.606(8) 0.298(3) 0.299(3) 0.071(10) Uiso d . 1 . H
H1N1 -0.258(6) 0.335(2) 0.592(2) 0.041(6) Uiso d . 1 . H
H2N1 -0.045(5) 0.457(3) 0.647(2) 0.038(6) Uiso d . 1 . H
H3N1 0.059(6) 0.3434(3) 0.599(2) 0.043(7) Uiso d . 1 . H
H1N2 -0.454(6) 0.129(3) 0.611(3) 0.054(8) Uiso d . 1 . H
H2N2 -0.552(7) 0.025(3) 0.696(3) 0.059(8) Uiso d . 1 . H
HC3 -0.343(7) 0.025(3) 0.906(3) 0.066(8) Uiso d . 1 . H
HC4 -0.063(7) 0.151(3) 1.070(3) 0.072(9) Uiso d . 1 . H
HC5 0.220(7) 0.373(3) 1.042(3) 0.070(9) Uiso d . 1 . H
HC6 0.191(6) 0.472(3) 0.848(2) 0.058(8) Uiso d . 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 113.40(10) y
O1 P1 O4 111.60(10) y
O2 P1 O4 110.60(10) y
O1 P1 O3 110.40(10) y
O2 P1 O3 105.20(10) y
O4 P1 O3 105.10(10) y
P1 O3 HO3 111.(3) n
P1 O4 HO4 115.(2) n
C1 N1 H1N1 110.9(15) n
C1 N1 H2N1 110.5(15) n
H1N1 N1 H2N1 109.(2) n
C1 N1 H3N1 111.3(17) n
H1N1 N1 H3N1 109.(2) n
H2N1 N1 H3N1 106.(2) n
C2 N2 H1N2 114.5(18) n
C2 N2 H2N2 110.4(19) n
H1N2 N2 H2N2 112.(3) n
C6 C1 C2 121.2(2) n
C6 C1 N1 118.3(2) n
C2 C1 N1 120.5(2) n
C1 C2 C3 117.5(2) n
C1 C2 N2 122.1(2) n
C3 C2 N2 120.2(2) n
C4 C3 C2 121.2(2) n
C4 C3 HC3 119.9(17) n
C2 C3 HC3 119.0(18) n
C5 C4 C3 120.7(2) n
C5 C4 HC4 122.(2) n
C3 C4 HC4 118.(2) n
C4 C5 C6 119.5(3) n
C4 C5 HC5 122.1(19) n
C6 C5 HC5 118.4(19) n
C5 C6 C1 120.0(2) n
C5 C6 HC6 121.3(16) n
C1 C6 HC6 118.6(16) n
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 O1 . 1.499(2) y
P1 O2 . 1.502(2) y
P1 O4 . 1.546(2) y
P1 O3 . 1.571(2) y
O3 HO3 . 0.76(3) n
O4 HO4 . 0.81(3) n
N1 C1 . 1.458(2) y
N1 H1N1 . 0.91(3) n
N1 H2N1 . 0.88(3) n
N1 H3N1 . 0.84(3) n
N2 C2 . 1.414(3) y
N2 H1N2 . 0.85(3) n
N2 H2N2 . 0.87(3) n
C1 C6 . 1.383(3) n
C1 C2 . 1.391(3) n
C2 C3 . 1.392(3) n
C3 C4 . 1.372(4) n
C3 HC3 . 0.94(3) n
C4 C5 . 1.372(4) n
C4 HC4 . 0.92(3) n
C5 C6 . 1.380(4) n
C5 HC5 . 0.91(3) n
C6 HC6 . 0.95(3) n
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
_geom_hbond_publ_flag
O3 HO3 N2 2_556 0.76(3) 1.99(3) 2.744(3) 169(3) y
O4 HO4 O2 1_655 0.81(3) 1.70(3) 2.513(2) 175(3) y
N1 H1N1 O1 1_455 0.91(3) 1.88(3) 2.784(2) 176(2) y
N1 H2N1 O2 2_566 0.89(3) 1.85(3) 2.731(2) 178(2) y
N1 H3N1 O1 . 0.84(3) 1.97(3) 2.809(3) 176(2) y
N2 H1N2 O1 1_455 0.85(3) 2.16(3) 2.972(3) 161(2) y
N2 H2N2 O3 2_456 0.87(3) 2.29(3) 3.051(3) 147(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14457194
