#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/34/2003443.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_2003443
loop_
_publ_author_name
'Ben Amor, F.'
'Soumhi, E. H.'
'Ould Abdellahi, M.'
'Jouini, T.'
_publ_section_title
;
 p-Anisidinium Dihydrogénophosphate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              933
_journal_page_last               935
_journal_paper_doi               10.1107/S0108270194014289
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C7 H12 N1 O5 P1'
_chemical_formula_structural     (1-4,CH~3~O-C~6~H~4~-NH~3~)H~2~PO~4~
_chemical_formula_sum            'C7 H12 N O5 P'
_chemical_formula_weight         221.15
_chemical_name_systematic
;
 para-Anisidinium Dihydrogénophosphate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.903(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3781(5)
_cell_length_b                   8.2216(6)
_cell_length_c                   13.5971(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      14
_cell_volume                     1013.11(10)
_computing_cell_refinement       'Enraf-Nonius CAD4 software'
_computing_data_collection       'Enraf-Nonius CAD4 software'
_computing_data_reduction        'MOLEN (Fair, 1990)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_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  0.0110
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1852
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        1.6
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            incolore
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       prisme
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.360
_refine_ls_extinction_coef       0.0525(45)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1994)'
_refine_ls_goodness_of_fit_all   1.130
_refine_ls_goodness_of_fit_obs   1.164
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_restrained_S_obs      1.164
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_obs          0.0394
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/[σ²(Fₒ²)+(0.0591P)²+0.3749P]
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1060
_refine_ls_wR_factor_obs         0.1033
_reflns_number_observed          1603
_reflns_number_total             1774
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            du1105.cif
_cod_data_source_block           fat1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(F~o~^2^)+(0.0591P)^2^+0.3749P]' 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^(F~o~^2^)+(0.0591P)^2^+0.3749P]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C7 H12 N1 O5 P1'
_cod_database_code               2003443
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
P 0.0257(3) 0.0020(2) 0.0064(2) 0.0290(3) 0.0047(2) 0.0323(3)
O1 0.0389(8) 0.0013(6) 0.0070(6) 0.0317(7) 0.0012(6) 0.0328(8)
O2 0.0260(7) 0.0035(6) 0.0102(6) 0.0399(8) 0.0095(7) 0.0577(10)
O3 0.0681(11) 0.0078(8) -0.0046(7) 0.0353(9) -0.0003(7) 0.0349(8)
O4 0.0319(8) 0.0066(7) 0.0175(7) 0.0453(9) 0.0176(7) 0.0555(10)
O5 0.0915(15) -0.0038(11) 0.0071(9) 0.0755(13) -0.0116(9) 0.0338(9)
N 0.0332(10) -0.0003(8) 0.0079(8) 0.0365(10) -0.0009(8) 0.0330(9)
C1 0.032(1) 0.0010(8) 0.0063(8) 0.036(1) -0.0023(8) 0.031(1)
C2 0.075(2) -0.022(1) 0.013(1) 0.047(1) -0.003(1) 0.039(1)
C3 0.088(2) -0.012(1) 0.021(1) 0.051(1) 0.003(1) 0.038(1)
C4 0.0536(1) 0.004(1) 0.007(1) 0.053(1) -0.007(1) 0.033(1)
C5 0.082(2) -0.030(2) 0.011(1) 0.060(2) -0.015(1) 0.046(1)
C6 0.076(2) -0.022(1) 0.016(1) 0.048(1) -0.002(1) 0.042(1)
C7 0.126(3) 0.020(2) 0.022(2) 0.083(2) -0.001(2) 0.037(1)
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
P 1 0.41440(5) 0.22869(6) 0.42869(4) 0.0292(2) Uani d P
O1 1 0.4796(2) 0.1971(2) 0.5408(1) 0.0349(4) Uani d O
O2 1 0.2678(1) 0.3132(2) 0.4043(1) 0.0413(4) Uani d O
O3 1 0.3975(2) 0.0647(2) 0.3692(1) 0.0494(5) Uani d O
O4 1 0.5194(2) 0.3386(2) 0.3851(1) 0.0431(4) Uani d O
O5 1 0.4281(2) 0.2623(3) 1.0530(1) 0.0686(6) Uani d O
N 1 0.2457(2) 0.1396(2) 0.6355(1) 0.0344(4) Uani d N
C1 1 0.2913(2) 0.1703(3) 0.7452(1) 0.0332(5) Uani d C
C2 1 0.2561(3) 0.0614(3) 0.8105(2) 0.0540(7) Uani d C
C3 1 0.2998(4) 0.0878(3) 0.9148(2) 0.0585(7) Uani d C
C4 1 0.3787(3) 0.2243(3) 0.9520(2) 0.0472(6) Uani d C
C5 1 0.4129(3) 0.3345(4) 0.8848(2) 0.0636(8) Uani d C
C6 1 0.3692(3) 0.3076(3) 0.7815(2) 0.0550(7) Uani d C
C7 1 0.3873(6) 0.1583(5) 1.1245(2) 0.0817(11) Uani d C
HO3 1 0.438(3) -0.010(4) 0.400(2) 0.067(9) Uiso d H
HO4 1 0.588(4) 0.300(4) 0.386(3) 0.074(11) Uiso d H
H1N 1 0.232(2) 0.027(3) 0.622(2) 0.045(6) Uiso d H
H2N 1 0.311(3) 0.175(3) 0.606(2) 0.046(7) Uiso d H
H3N 1 0.161(3) 0.189(3) 0.605(2) 0.040(6) Uiso d H
HC2 1 0.207(3) -0.029(4) 0.788(2) 0.071(9) Uiso d H
HC3 1 0.277(3) 0.013(4) 0.956(2) 0.072(9) Uiso d H
HC5 1 0.469(4) 0.429(4) 0.912(2) 0.085(10) Uiso d H
HC6 1 0.393(3) 0.379(4) 0.734(2) 0.076(9) Uiso d H
H1C7 1 0.407(4) 0.049(5) 1.119(2) 0.082(11) Uiso d H
H2C7 1 0.435(3) 0.202(4) 1.187(3) 0.082(10) Uiso d H
H3C7 1 0.274(4) 0.170(4) 1.114(2) 0.091(12) Uiso d H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
P P 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1023 0.094
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000
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
O2 P O1 114.37(9) y
O2 P O3 108.70(10) y
O1 P O3 109.59(8) y
O2 P O4 106.26(8) y
O1 P O4 110.55(8) y
O3 P O4 107.00(10) y
P O4 HO4 113(3) no
P O3 HO3 116(2) no
C4 O5 C7 117.9(3) y
C1 N H1N 111.0(10) no
C1 N H2N 111(2) no
H1N N H2N 108(2) no
C1 N H3N 113.0(10) no
H1N N H3N 107(2) no
H2N N H3N 107(2) no
C2 C1 C6 120.3(2) y
C2 C1 N 119.7(2) y
C6 C1 N 120.0(2) y
C1 C2 C3 120.4(2) y
C1 C2 HC2 121(2) no
C3 C2 HC2 118(2) no
C4 C3 C2 119.7(2) y
C4 C3 HC3 122(2) no
C2 C3 HC3 119(2) no
C3 C4 O5 124.8(2) y
C3 C4 C5 119.3(2) y
O5 C4 C5 115.9(2) y
C6 C5 C4 120.7(2) y
C6 C5 HC5 121(2) no
C4 C5 HC5 119(2) no
C1 C6 C5 119.6(2) y
C1 C6 HC6 118(2) no
C5 C6 HC6 122(2) no
O5 C7 H1C7 116(2) no
O5 C7 H2C7 104(2) no
H1C7 C7 H2C7 112(3) no
O5 C7 H3C7 107(2) no
H1C7 C7 H3C7 108(3) no
H2C7 C7 H3C7 109(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P O2 1.4990(10) y
P O1 1.5120(10) y
P O3 1.559(2) y
P O4 1.561(2) y
O4 HO4 0.71(3) no
O3 HO3 0.79(3) no
O5 C4 1.368(3) y
O5 C7 1.419(4) y
N C1 1.463(2) y
N H1N 0.95(3) no
N H2N 0.86(3) no
N H3N 0.90(3) no
C1 C2 1.361(3) y
C1 C6 1.366(3) y
C2 C3 1.387(3) y
C2 HC2 0.89(3) no
C3 C4 1.367(4) y
C3 HC3 0.89(3) no
C4 C5 1.381(4) y
C5 C6 1.376(3) y
C5 HC5 0.96(3) no
C6 HC6 0.94(3) no
C7 H1C7 0.92(4) no
C7 H2C7 0.93(4) no
C7 H3C7 1.04(4) no
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
C6 C1 C2 C3 -0.5(4)
N C1 C2 C3 179.3(2)
C1 C2 C3 C4 0.1(5)
C2 C3 C4 O5 -179.7(3)
C2 C3 C4 C5 0.4(5)
C7 O5 C4 C3 -4.0(4)
C7 O5 C4 C5 175.9(3)
C3 C4 C5 C6 -0.4(5)
O5 C4 C5 C6 179.6(3)
C2 C1 C6 C5 0.4(4)
N C1 C6 C5 -179.4(2)
C4 C5 C6 C1 0.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21138987
