#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/53/2235308.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_2235308
loop_
_publ_author_name
'Wang, Ying-Chun'
_publ_section_title
;
 4-Hydroxyanilinium 2-chloroacetate
;
_journal_coeditor_code           XU5534
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1883
_journal_paper_doi               10.1107/S1600536812021411
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H8 N O +, C2 H2 Cl O2 -'
_chemical_formula_moiety         'C6 H8 N O +, C2 H2 Cl O2 -'
_chemical_formula_sum            'C8 H10 Cl N O3'
_chemical_formula_weight         203.62
_chemical_name_systematic
;
4-Hydroxyanilinium 2-chloroacetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.825(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.702(3)
_cell_length_b                   4.5242(10)
_cell_length_c                   19.357(7)
_cell_measurement_reflns_used    2122
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.68
_cell_volume                     930.6(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       'CCD profile fitting'
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6248
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1699
_reflns_number_total             2122
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5534.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235308
_cod_database_fobs_code          2235308
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
Cl Cl1 0.41622(5) 1.32273(13) 0.29181(3) 0.02016(16) Uani d . 1 1
O O3 0.29262(14) 0.7514(4) 0.42037(8) 0.0222(4) Uani d . 1 1
O O2 0.48355(14) 0.9420(4) 0.41518(8) 0.0188(4) Uani d . 1 1
N N1 0.37140(16) 0.5601(4) 0.55354(10) 0.0163(4) Uani d D 1 1
H H1A 0.3555 0.6038 0.5074 0.024 Uiso calc RD 1 1
H H1B 0.4170 0.3902 0.5590 0.024 Uiso calc RD 1 1
H H1C 0.4158 0.7104 0.5760 0.024 Uiso calc RD 1 1
O O1 -0.08865(14) 0.4356(4) 0.66202(9) 0.0250(4) Uani d D 1 1
H H1 -0.1461 0.3684 0.6347 0.037 Uiso d RD 1 1
C C2 0.1616(2) 0.3348(6) 0.54972(13) 0.0223(5) Uani d . 1 1
H H2A 0.1781 0.2289 0.5094 0.027 Uiso calc R 1 1
C C7 0.3694(2) 0.9122(5) 0.39246(11) 0.0163(5) Uani d . 1 1
C C1 0.2513(2) 0.5212(5) 0.58293(12) 0.0164(5) Uani d . 1 1
C C6 0.2298(2) 0.6739(6) 0.64231(12) 0.0204(5) Uani d . 1 1
H H6A 0.2929 0.7995 0.6651 0.025 Uiso calc R 1 1
C C4 0.0232(2) 0.4565(5) 0.63473(12) 0.0184(5) Uani d . 1 1
C C5 0.1148(2) 0.6413(6) 0.66814(12) 0.0235(5) Uani d . 1 1
H H5A 0.0989 0.7458 0.7088 0.028 Uiso calc R 1 1
C C3 0.0466(2) 0.3032(6) 0.57581(13) 0.0231(5) Uani d . 1 1
H H3A -0.0159 0.1760 0.5531 0.028 Uiso calc R 1 1
C C8 0.3133(2) 1.0670(5) 0.32664(12) 0.0191(5) Uani d . 1 1
H H8A 0.2366 1.1738 0.3364 0.023 Uiso calc R 1 1
H H8B 0.2873 0.9156 0.2909 0.023 Uiso calc R 1 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'
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
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
C4 O1 H1 113.6
C1 C2 C3 119.4(2)
C1 C2 H2A 120.3
C3 C2 H2A 120.3
O2 C7 O3 124.5(2)
O2 C7 C8 121.14(19)
O3 C7 C8 114.38(19)
C2 C1 C6 121.2(2)
C2 C1 N1 118.9(2)
C6 C1 N1 119.9(2)
C1 C6 C5 119.2(2)
C1 C6 H6A 120.4
C5 C6 H6A 120.4
O1 C4 C3 122.4(2)
O1 C4 C5 117.6(2)
C3 C4 C5 119.9(2)
C4 C5 C6 120.2(2)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
C4 C3 C2 120.1(2)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C7 C8 Cl1 114.65(16)
C7 C8 H8A 108.6
Cl1 C8 H8A 108.6
C7 C8 H8B 108.6
Cl1 C8 H8B 108.6
H8A C8 H8B 107.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C8 1.784(2)
O3 C7 1.265(3)
O2 C7 1.256(3)
N1 C1 1.477(3)
N1 H1A 0.9100
N1 H1B 0.9100
N1 H1C 0.9100
O1 C4 1.368(3)
O1 H1 0.8203
C2 C1 1.378(3)
C2 C3 1.392(3)
C2 H2A 0.9500
C7 C8 1.514(3)
C1 C6 1.384(3)
C6 C5 1.390(3)
C6 H6A 0.9500
C4 C3 1.383(3)
C4 C5 1.389(3)
C5 H5A 0.9500
C3 H3A 0.9500
C8 H8A 0.9900
C8 H8B 0.9900
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
N1 H1A O3 . 0.91 1.86 2.755(3) 166.0
N1 H1B O2 3_666 0.91 1.87 2.777(3) 171.1
N1 H1C O2 3_676 0.91 1.90 2.762(2) 156.6
O1 H1 O3 3_566 0.82 1.87 2.683(2) 171.6
C8 H8A O1 3_576 0.99 2.38 3.319(3) 159
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
C3 C2 C1 C6 1.0(4)
C3 C2 C1 N1 -178.1(2)
C2 C1 C6 C5 -1.0(4)
N1 C1 C6 C5 178.2(2)
O1 C4 C5 C6 -179.3(2)
C3 C4 C5 C6 0.3(4)
C1 C6 C5 C4 0.3(4)
O1 C4 C3 C2 179.3(2)
C5 C4 C3 C2 -0.3(4)
C1 C2 C3 C4 -0.4(4)
O2 C7 C8 Cl1 -7.3(3)
O3 C7 C8 Cl1 173.97(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657836
