#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227986.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_2227986
loop_
_publ_author_name
'Naz, Syeda Sohaila'
'Islam, Nazar Ul'
'Tahir, M. Nawaz'
_publ_section_title
;
 5-Carboxy-2,4-dihydroxyanilinium chloride
;
_journal_coeditor_code           SI2289
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2372
_journal_paper_doi               10.1107/S1600536810033337
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H8 N O4 +, Cl -'
_chemical_formula_moiety         'C7 H8 N O4 +, Cl -'
_chemical_formula_sum            'C7 H8 Cl N O4'
_chemical_formula_weight         205.59
_chemical_name_systematic
;
5-Carboxy-2,4-dihydroxyanilinium chloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 97.649(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0667(3)
_cell_length_b                   28.4071(13)
_cell_length_c                   6.3966(3)
_cell_measurement_reflns_used    1108
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      2.87
_cell_volume                     912.47(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.10
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7094
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.215
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0360P)²+0.4226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1108
_reflns_number_total             1635
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2289.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227986
_cod_database_fobs_code          2227986
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.8567(5) 0.05383(8) -0.1244(4) 0.0527(8) Uani . . 1.000
O O2 0.7828(4) 0.01248(8) 0.1583(3) 0.0553(8) Uani . . 1.000
O O3 0.4286(5) 0.04378(8) 0.3905(4) 0.0620(10) Uani . . 1.000
O O4 0.0113(4) 0.18833(7) 0.1726(3) 0.0498(8) Uani . . 1.000
N N1 0.2950(5) 0.19898(8) -0.1420(4) 0.0404(8) Uani . . 1.000
C C1 0.7367(6) 0.04694(11) 0.0429(5) 0.0420(11) Uani . . 1.000
C C2 0.5471(5) 0.08321(10) 0.0823(4) 0.0373(10) Uani . . 1.000
C C3 0.4020(6) 0.08012(10) 0.2540(5) 0.0404(10) Uani . . 1.000
C C4 0.2197(6) 0.11460(10) 0.2882(5) 0.0415(11) Uani . . 1.000
C C5 0.1841(6) 0.15295(10) 0.1561(4) 0.0366(10) Uani . . 1.000
C C6 0.3332(6) 0.15690(10) -0.0114(4) 0.0343(9) Uani . . 1.000
C C7 0.5084(6) 0.12258(10) -0.0495(4) 0.0376(10) Uani . . 1.000
Cl Cl1 0.75184(16) 0.19834(3) 0.56278(12) 0.0476(3) Uani . . 1.000
H H1 0.974(7) 0.0328(12) -0.131(5) 0.0632 Uiso . . 1.000
H H1A 0.13993 0.19710 -0.22519 0.0485 Uiso . . 1.000
H H1B 0.42649 0.20130 -0.22080 0.0485 Uiso . . 1.000
H H1C 0.29515 0.22425 -0.05970 0.0485 Uiso . . 1.000
H H3 0.543(7) 0.0264(13) 0.342(5) 0.0743 Uiso . . 1.000
H H4 0.12136 0.11186 0.40041 0.0498 Uiso . . 1.000
H H4A -0.063(6) 0.1874(11) 0.284(5) 0.0597 Uiso . . 1.000
H H7 0.60291 0.12534 -0.16402 0.0451 Uiso . . 1.000
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'
Cl Cl 0.1484 0.1585 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . . 110(2) no
C3 O3 H3 . . . 103(2) no
C5 O4 H4A . . . 114(2) no
C6 N1 H1C . . . 109.00 no
H1A N1 H1B . . . 109.00 no
C6 N1 H1A . . . 109.00 no
C6 N1 H1B . . . 109.00 no
H1B N1 H1C . . . 109.00 no
H1A N1 H1C . . . 109.00 no
O1 C1 C2 . . . 115.1(3) no
O1 C1 O2 . . . 122.4(3) no
O2 C1 C2 . . . 122.5(3) no
C1 C2 C7 . . . 120.4(2) no
C3 C2 C7 . . . 118.4(3) no
C1 C2 C3 . . . 121.2(3) no
O3 C3 C4 . . . 116.8(3) no
C2 C3 C4 . . . 120.7(3) no
O3 C3 C2 . . . 122.5(3) no
C3 C4 C5 . . . 120.0(3) no
C4 C5 C6 . . . 119.7(3) no
O4 C5 C6 . . . 115.1(2) no
O4 C5 C4 . . . 125.2(3) no
N1 C6 C5 . . . 117.5(3) no
N1 C6 C7 . . . 121.7(2) no
C5 C6 C7 . . . 120.8(3) no
C2 C7 C6 . . . 120.5(3) no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C2 C7 H7 . . . 120.00 no
C6 C7 H7 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.314(4) no
O2 C1 . . 1.230(4) no
O3 C3 . . 1.347(4) no
O4 C5 . . 1.346(4) no
O1 H1 . . 0.85(3) no
O3 H3 . . 0.85(4) no
O4 H4A . . 0.85(3) no
N1 C6 . . 1.456(4) no
N1 H1A . . 0.8900 no
N1 H1B . . 0.8900 no
N1 H1C . . 0.8900 no
C1 C2 . . 1.453(4) no
C2 C7 . . 1.399(4) no
C2 C3 . . 1.403(4) no
C3 C4 . . 1.384(4) no
C4 C5 . . 1.376(4) no
C5 C6 . . 1.395(4) no
C6 C7 . . 1.362(4) no
C4 H4 . . 0.9300 no
C7 H7 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 N1 3.176(3) . 1_556 no
Cl1 N1 3.124(3) . 1_656 no
Cl1 C7 3.622(3) . 1_556 no
Cl1 O4 2.985(2) . 1_655 no
Cl1 N1 3.217(2) . 4_555 no
Cl1 H4A 2.15(3) . 1_655 no
Cl1 H1A 2.2400 . 1_656 no
Cl1 H1B 2.2900 . 1_556 no
Cl1 H1C 2.3500 . 4_555 no
Cl1 H7 2.8800 . 1_556 no
O1 O2 2.653(3) . 3_755 no
O2 O3 2.632(3) . . no
O2 C1 3.245(4) . 3_655 no
O2 O1 2.653(3) . 3_755 no
O2 C1 3.357(4) . 3_755 no
O3 O3 2.899(3) . 3_656 no
O3 O2 2.632(3) . . no
O4 N1 2.642(3) . . no
O4 Cl1 2.985(2) . 1_455 no
O4 C7 3.322(4) . 1_455 no
O1 H7 2.4000 . . no
O2 H3 1.84(3) . . no
O2 H1 1.81(3) . 3_755 no
O3 H3 2.62(3) . 3_656 no
O4 H1C 2.4300 . . no
O4 H1A 2.7200 . . no
N1 Cl1 3.176(3) . 1_554 no
N1 Cl1 3.124(3) . 1_454 no
N1 O4 2.642(3) . . no
N1 Cl1 3.217(2) . 4_454 no
C1 C3 3.587(4) . 1_655 no
C1 C1 3.580(4) . 3_655 no
C1 O2 3.245(4) . 3_655 no
C1 O2 3.357(4) . 3_755 no
C1 C4 3.335(4) . 1_655 no
C2 C4 3.598(4) . 1_655 no
C3 C1 3.587(4) . 1_455 no
C4 C2 3.598(4) . 1_455 no
C4 C1 3.335(4) . 1_455 no
C7 O4 3.322(4) . 1_655 no
C7 Cl1 3.622(3) . 1_554 no
C1 H1 2.72(3) . 3_755 no
C1 H3 2.34(3) . . no
H1 O2 1.81(3) . 3_755 no
H1 C1 2.72(3) . 3_755 no
H1 H1 2.50(5) . 3_755 no
H1A Cl1 2.2400 . 1_454 no
H1A O4 2.7200 . . no
H1B H7 2.3500 . . no
H1B Cl1 2.2900 . 1_554 no
H1C O4 2.4300 . . no
H1C Cl1 2.3500 . 4_454 no
H3 C1 2.34(3) . . no
H3 O2 1.84(3) . . no
H3 H3 2.60(5) . 3_656 no
H3 O3 2.62(3) . 3_656 no
H4 H4A 2.4200 . . no
H4A H4 2.4200 . . no
H4A Cl1 2.15(3) . 1_455 no
H7 Cl1 2.8800 . 1_554 no
H7 O1 2.4000 . . no
H7 H1B 2.3500 . . no
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 O2 3_755 0.85(3) 1.81(3) 2.653(3) 177(4) yes
N1 H1A Cl1 1_454 0.89 2.24 3.124(3) 176 yes
N1 H1B Cl1 1_554 0.89 2.29 3.176(3) 173 yes
N1 H1C Cl1 4_454 0.89 2.35 3.217(2) 163 yes
O3 H3 O2 . 0.85(4) 1.84(3) 2.632(3) 154(3) yes
O4 H4A Cl1 1_455 0.85(3) 2.15(3) 2.985(2) 170(3) 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
O1 C1 C2 C3 . . . . 179.2(3) no
O1 C1 C2 C7 . . . . -1.8(4) no
O2 C1 C2 C3 . . . . -1.2(5) no
O2 C1 C2 C7 . . . . 177.8(3) no
C1 C2 C3 O3 . . . . -0.2(4) no
C1 C2 C3 C4 . . . . -179.2(3) no
C7 C2 C3 O3 . . . . -179.2(3) no
C7 C2 C3 C4 . . . . 1.8(4) no
C1 C2 C7 C6 . . . . -179.2(3) no
C3 C2 C7 C6 . . . . -0.2(4) no
O3 C3 C4 C5 . . . . 179.4(3) no
C2 C3 C4 C5 . . . . -1.6(5) no
C3 C4 C5 O4 . . . . 179.3(3) no
C3 C4 C5 C6 . . . . -0.2(4) no
O4 C5 C6 N1 . . . . 2.6(4) no
O4 C5 C6 C7 . . . . -177.7(3) no
C4 C5 C6 N1 . . . . -177.8(3) no
C4 C5 C6 C7 . . . . 1.9(4) no
N1 C6 C7 C2 . . . . 178.0(3) no
C5 C6 C7 C2 . . . . -1.7(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656303
