#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228391.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228391
loop_
_publ_author_name
'Li, He-Ping'
'Ng, Seik Weng'
_publ_section_title
;
 Ammonium 4-(4-carboxyphenoxy)benzoate
;
_journal_coeditor_code           HG2754
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3345
_journal_paper_doi               10.1107/S1600536810048841
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'N H4 +, C14 H9 O5 -'
_chemical_formula_moiety         'H4 N +, C14 H9 O5 -'
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.25
_chemical_name_systematic
;
Ammonium 4-(4-carboxyphenoxy)benzoate
;
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.19160(10)
_cell_length_b                   28.5483(6)
_cell_length_c                   7.11230(10)
_cell_measurement_reflns_used    2311
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.9
_cell_volume                     1257.17(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3444
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.418
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0922P)²+0.4317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                1279
_reflns_number_total             1434
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2754.cif
_cod_data_source_block           I
_cod_database_code               2228391
_cod_database_fobs_code          2228391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, 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
O O1 0.83559(19) 0.46053(3) 0.15346(17) 0.0429(4) Uani d D 1 . .
H H1 0.748(8) 0.4828(15) 0.140(6) 0.10(2) Uiso d PD 0.50 A -1
O O2 0.5981(2) 0.43933(4) 0.37136(18) 0.0536(4) Uani d . 1 . .
O O3 1.1215(2) 0.2500 0.2500 0.0325(4) Uani d S 1 . .
C C1 0.7477(2) 0.43024(5) 0.26451(19) 0.0320(3) Uani d . 1 . .
C C2 0.8424(2) 0.38203(4) 0.25651(17) 0.0266(3) Uani d . 1 . .
C C3 0.7341(2) 0.34508(5) 0.34202(18) 0.0302(3) Uani d . 1 . .
H H3 0.6034 0.3506 0.4026 0.036 Uiso calc R 1 . .
C C4 0.8184(2) 0.30004(5) 0.33813(18) 0.0304(3) Uani d . 1 . .
H H4 0.7450 0.2754 0.3950 0.036 Uiso calc R 1 . .
C C5 1.0136(2) 0.29244(4) 0.24811(16) 0.0254(3) Uani d . 1 . .
C C6 1.1244(2) 0.32879(5) 0.16242(18) 0.0292(3) Uani d . 1 . .
H H6 1.2555 0.3232 0.1027 0.035 Uiso calc R 1 . .
C C7 1.0374(2) 0.37357(4) 0.16673(18) 0.0298(3) Uani d . 1 . .
H H7 1.1105 0.3981 0.1089 0.036 Uiso calc R 1 . .
N N1 0.2500 0.5000 0.2884(4) 0.0503(5) Uani d SD 1 . .
H H11 0.3506(16) 0.5123(6) 0.2161(16) 0.060 Uiso d D 1 . .
H H12 0.308(3) 0.4771(5) 0.355(2) 0.060 Uiso d D 1 . .
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
O1 0.0450(7) 0.0203(5) 0.0633(8) 0.0051(4) 0.0098(5) 0.0037(4)
O2 0.0553(8) 0.0374(6) 0.0681(8) 0.0191(5) 0.0230(6) 0.0050(5)
O3 0.0327(7) 0.0164(6) 0.0485(8) 0.000 0.000 -0.0001(5)
C1 0.0339(7) 0.0233(6) 0.0387(7) 0.0044(5) -0.0013(5) -0.0041(5)
C2 0.0321(7) 0.0194(6) 0.0284(6) 0.0019(5) -0.0005(5) -0.0016(4)
C3 0.0309(7) 0.0269(7) 0.0329(7) 0.0015(5) 0.0058(5) -0.0014(5)
C4 0.0366(7) 0.0223(6) 0.0323(7) -0.0030(5) 0.0062(5) 0.0024(5)
C5 0.0328(7) 0.0167(6) 0.0266(6) 0.0011(4) -0.0016(5) -0.0020(4)
C6 0.0308(7) 0.0219(6) 0.0350(7) 0.0006(5) 0.0070(5) -0.0013(5)
C7 0.0360(8) 0.0183(6) 0.0352(7) -0.0012(5) 0.0062(5) 0.0019(4)
N1 0.0342(10) 0.0516(12) 0.0651(13) 0.0082(9) 0.000 0.000
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'
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 O1 H1 . . 108(4) ?
C5 O3 C5 4 . 122.29(15) ?
O2 C1 O1 . . 123.76(13) ?
O2 C1 C2 . . 120.94(13) ?
O1 C1 C2 . . 115.30(12) ?
C7 C2 C3 . . 119.32(11) ?
C7 C2 C1 . . 121.23(12) ?
C3 C2 C1 . . 119.45(12) ?
C4 C3 C2 . . 120.83(12) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C5 C4 C3 . . 118.86(12) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
O3 C5 C4 . . 123.65(11) ?
O3 C5 C6 . . 114.94(12) ?
C4 C5 C6 . . 121.19(11) ?
C5 C6 C7 . . 119.25(12) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C2 C7 C6 . . 120.55(12) ?
C2 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
H11 N1 H12 . . 108.6(10) ?
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
O1 C1 . 1.2914(18) ?
O1 H1 . 0.841(10) ?
O2 C1 . 1.2260(18) ?
O3 C5 4 1.3833(13) ?
O3 C5 . 1.3833(13) ?
C1 C2 . 1.4973(17) ?
C2 C7 . 1.3867(19) ?
C2 C3 . 1.3902(18) ?
C3 C4 . 1.3880(18) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3852(18) ?
C6 C7 . 1.3876(17) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
N1 H11 . 0.881(7) ?
N1 H12 . 0.882(8) ?
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
O1 H1 O1 2_665 0.840(10) 1.70(3) 2.490(2) 156(6) yes
N1 H11 O1 2_665 0.880(10) 2.140(10) 2.962(2) 155.0(10) yes
N1 H12 O2 . 0.880(10) 2.10(2) 2.8270(10) 139(2) yes
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
O2 C1 C2 C7 . . . . -166.60(14) ?
O1 C1 C2 C7 . . . . 12.97(19) ?
O2 C1 C2 C3 . . . . 12.8(2) ?
O1 C1 C2 C3 . . . . -167.60(13) ?
C7 C2 C3 C4 . . . . -0.1(2) ?
C1 C2 C3 C4 . . . . -179.57(12) ?
C2 C3 C4 C5 . . . . 0.3(2) ?
C5 O3 C5 C4 4 . . . 33.86(10) ?
C5 O3 C5 C6 4 . . . -151.57(12) ?
C3 C4 C5 O3 . . . . 174.06(11) ?
C3 C4 C5 C6 . . . . -0.17(19) ?
O3 C5 C6 C7 . . . . -174.86(10) ?
C4 C5 C6 C7 . . . . -0.15(19) ?
C3 C2 C7 C6 . . . . -0.20(19) ?
C1 C2 C7 C6 . . . . 179.23(12) ?
C5 C6 C7 C2 . . . . 0.3(2) ?
