#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222582.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_2222582
loop_
_publ_author_name
'Shafiq, Muhammad'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Khan, Muneeb Hayat'
'Simpson, Jim'
_publ_section_title
;
 2-(Methoxycarbonyl)anilinium dihydrogen phosphate
;
_journal_coeditor_code           BT2987
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1786
_journal_paper_doi               10.1107/S1600536809025252
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H10 N O2 +, H2 P O4 -'
_chemical_formula_moiety         'C8 H10 N O2 +, H2 O4 P -'
_chemical_formula_sum            'C8 H12 N O6 P'
_chemical_formula_weight         249.16
_chemical_name_common
;
2-(Methoxycarbonyl)anilinium dihydrogen phosphate
;
_chemical_name_systematic
;
2-(Methoxycarbonyl)anilinium dihydrogen phosphate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 114.970(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.939(3)
_cell_length_b                   4.7880(5)
_cell_length_c                   22.283(4)
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.24
_cell_volume                     2025.2(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al.,
2004), PLATON (Spek, 2009)
and publCIF (Westrip, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10812
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.482
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²+1.6713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2078
_reflns_number_total             2413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2987.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222582
_cod_database_fobs_code          2222582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.24287(7) 0.4968(3) 0.93401(6) 0.0200(3) Uani d . 1 . .
H H1A 0.2695 0.3443 0.9473 0.030 Uiso calc R 1 . .
H H1B 0.2127 0.5014 0.9526 0.030 Uiso calc R 1 . .
H H1C 0.2702 0.6478 0.9460 0.030 Uiso calc R 1 . .
C C1 0.20379(8) 0.4920(3) 0.86203(7) 0.0202(3) Uani d . 1 . .
C C2 0.14685(8) 0.3118(3) 0.83134(7) 0.0227(3) Uani d . 1 . .
C C3 0.11163(9) 0.3157(4) 0.76239(8) 0.0300(4) Uani d . 1 . .
H H3 0.0730 0.1996 0.7412 0.036 Uiso calc R 1 . .
C C4 0.13337(10) 0.4893(4) 0.72527(9) 0.0326(4) Uani d . 1 . .
H H4 0.1102 0.4864 0.6793 0.039 Uiso calc R 1 . .
C C5 0.18948(10) 0.6671(4) 0.75648(9) 0.0322(4) Uani d . 1 . .
H H5 0.2038 0.7857 0.7315 0.039 Uiso calc R 1 . .
C C6 0.22462(9) 0.6700(4) 0.82496(8) 0.0273(4) Uani d . 1 . .
H H6 0.2622 0.7916 0.8459 0.033 Uiso calc R 1 . .
C C7 0.12565(8) 0.1075(3) 0.86989(8) 0.0225(3) Uani d . 1 . .
C C8 0.03453(11) -0.1887(5) 0.86660(11) 0.0433(5) Uani d . 1 . .
H H8A 0.0609 -0.1795 0.9138 0.065 Uiso calc R 1 . .
H H8B 0.0402 -0.3700 0.8511 0.065 Uiso calc R 1 . .
H H8C -0.0144 -0.1566 0.8555 0.065 Uiso calc R 1 . .
O O1 0.16391(6) 0.0261(3) 0.92428(6) 0.0273(3) Uani d . 1 . .
O O2 0.05989(7) 0.0218(3) 0.83567(7) 0.0380(3) Uani d . 1 . .
P P1 0.10739(2) 0.56312(8) 0.531833(19) 0.01826(13) Uani d . 1 . .
O O3 0.17510(6) 0.5066(2) 0.52576(6) 0.0248(3) Uani d . 1 . .
O O4 0.05239(6) 0.6781(3) 0.46425(6) 0.0262(3) Uani d . 1 . .
H H4O 0.0163(12) 0.681(5) 0.4598(10) 0.031 Uiso d . 1 . .
O O5 0.12078(7) 0.8011(3) 0.58427(6) 0.0323(3) Uani d . 1 . .
H H5O 0.1063(13) 0.948(5) 0.5709(11) 0.039 Uiso d . 1 . .
O O6 0.07879(6) 0.3146(2) 0.55400(6) 0.0255(3) Uani d . 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_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 ?
C6 C1 C2 . . 120.64(15) ?
C6 C1 N1 . . 118.39(14) ?
C2 C1 N1 . . 120.97(14) ?
C1 C2 C3 . . 118.45(15) ?
C1 C2 C7 . . 121.69(14) ?
C3 C2 C7 . . 119.77(15) ?
C4 C3 C2 . . 120.91(17) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 119.79(16) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.33(17) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 119.85(16) ?
C1 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
O1 C7 O2 . . 124.62(16) ?
O1 C7 C2 . . 124.15(15) ?
O2 C7 C2 . . 111.21(14) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 O2 C8 . . 116.33(15) ?
O3 P1 O6 . . 114.06(7) ?
O3 P1 O4 . . 108.44(7) ?
O6 P1 O4 . . 111.21(7) ?
O3 P1 O5 . . 108.56(7) ?
O6 P1 O5 . . 107.47(7) ?
O4 P1 O5 . . 106.83(7) ?
P1 O4 H4O . . 116.4(17) ?
P1 O5 H5O . . 117.1(18) ?
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 . 1.4609(19) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C1 C6 . 1.379(2) ?
C1 C2 . 1.395(2) ?
C2 C3 . 1.396(2) ?
C2 C7 . 1.488(2) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.2010(19) ?
C7 O2 . 1.326(2) ?
C8 O2 . 1.443(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
P1 O3 . 1.5045(12) ?
P1 O6 . 1.5062(12) ?
P1 O4 . 1.5597(12) ?
P1 O5 . 1.5702(13) ?
O4 H4O . 0.72(2) ?
O5 H5O . 0.78(2) ?
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
C4 H4 O5 . 0.93 2.68 3.387(2) 133.1
C4 H4 O6 . 0.93 2.71 3.590(2) 157.8
C3 H3 O2 2_556 0.93 2.72 3.609(2) 161.5
N1 H1A O3 4_546 0.89 1.93 2.8218(18) 178.3
N1 H1A O5 4_546 0.89 2.68 3.190(2) 117.6
N1 H1C O3 4_556 0.89 2.01 2.9005(18) 174.8
N1 H1B O3 6_566 0.89 2.09 2.9400(17) 159.8
O5 H5O O6 1_565 0.78(2) 1.83(2) 2.6021(17) 170(2)
O4 H4O O6 5_566 0.72(2) 1.88(2) 2.6015(17) 179(2)
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
C6 C1 C2 C3 . . . . 0.1(2) ?
N1 C1 C2 C3 . . . . -179.80(15) ?
C6 C1 C2 C7 . . . . 176.75(15) ?
N1 C1 C2 C7 . . . . -3.1(2) ?
C1 C2 C3 C4 . . . . 1.3(3) ?
C7 C2 C3 C4 . . . . -175.43(16) ?
C2 C3 C4 C5 . . . . -1.7(3) ?
C3 C4 C5 C6 . . . . 0.7(3) ?
C2 C1 C6 C5 . . . . -1.1(3) ?
N1 C1 C6 C5 . . . . 178.83(15) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
C1 C2 C7 O1 . . . . -21.1(2) ?
C3 C2 C7 O1 . . . . 155.53(17) ?
C1 C2 C7 O2 . . . . 160.61(16) ?
C3 C2 C7 O2 . . . . -22.8(2) ?
O1 C7 O2 C8 . . . . -1.5(3) ?
C2 C7 O2 C8 . . . . 176.80(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655824
