#------------------------------------------------------------------------------
#$Date: 2022-05-03 05:39:52 +0300 (Tue, 03 May 2022) $
#$Revision: 274835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/69/1566904.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_1566904
loop_
_publ_author_name
'Obidova, Nodira'
'Ashurov, Jamshid'
'Izotova, Lidiya'
'Ibragimov, Bakhtiyar'
_publ_section_title
;
 2-Hydroxyethylammonium [2-(2,6-dichloroanilino)phenyl]acetate monohydrate
;
_journal_coeditor_code           BH4068
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x220441
_journal_paper_doi               10.1107/S2414314622004412
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C2 H8 N O +, C14 H10 Cl2 N O2 -, H2 O'
_chemical_formula_moiety         'C2 H8 N O +, C14 H10 Cl2 N O2 -, H2 O'
_chemical_formula_sum            'C16 H20 Cl2 N2 O4'
_chemical_formula_weight         375.24
_chemical_name_systematic
;
2-Hydroxyethylammonium [2-(2,6-dichloroanilino)phenyl]acetate monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 103.546(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1257(10)
_cell_length_b                   9.3864(5)
_cell_length_c                   10.0502(6)
_cell_measurement_reflns_used    2166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8450
_cell_measurement_theta_min      4.7260
_cell_volume                     1754.04(17)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
XP (Siemens, 1994), Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Agilent Technologies Xcalibur, Ruby'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12416
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.497
_diffrn_reflns_theta_min         4.757
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0505
_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)+(0.0614P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                2431
_reflns_number_total             3621
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bh4068sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1754.05(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566904
_shelx_estimated_absorpt_t_min   0.35618
_shelx_estimated_absorpt_t_max   1.0000
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.46202(4) 0.95109(8) 0.76764(8) 0.0441(2) Uani d 1 . .
Cl Cl2 0.24250(4) 1.20690(9) 0.40514(9) 0.0500(2) Uani d 1 . .
O O1 0.15000(11) 0.9926(2) 0.5897(2) 0.0472(6) Uani d 1 . .
O O1W 0.07192(13) 0.6316(3) 0.8457(2) 0.0558(6) Uani d 1 . .
H H1WA 0.103624 0.612215 0.917982 0.084 Uiso d 1 . .
H H1WB 0.085392 0.710654 0.818732 0.084 Uiso d 1 . .
N N1 0.30390(13) 0.9959(2) 0.6226(3) 0.0379(6) Uani d 1 . .
H H1 0.269351 1.041181 0.645204 0.045 Uiso calc 1 . .
O O2 0.08825(11) 0.8748(3) 0.7146(2) 0.0592(7) Uani d 1 . .
N N2 0.03573(14) 0.1808(3) 0.4921(3) 0.0446(6) Uani d 1 . .
H H2A 0.003371 0.148791 0.419647 0.054 Uiso calc 1 . .
H H2B 0.015651 0.187499 0.563284 0.054 Uiso calc 1 . .
H H2C 0.072670 0.120586 0.512028 0.054 Uiso calc 1 . .
O O3 0.07091(17) 0.3857(3) 0.6928(3) 0.0762(9) Uani d 1 . .
H H3A 0.073883 0.464400 0.729146 0.114 Uiso calc 1 . .
C C2 0.42880(15) 1.0634(3) 0.6305(3) 0.0327(6) Uani d 1 . .
C C14 0.14604(15) 0.9162(3) 0.6906(3) 0.0371(7) Uani d 1 . .
C C1 0.35476(15) 1.0754(3) 0.5751(3) 0.0322(6) Uani d 1 . .
C C12 0.26283(14) 0.7823(3) 0.7158(3) 0.0342(6) Uani d 1 . .
C C7 0.30532(15) 0.8463(3) 0.6360(3) 0.0342(6) Uani d 1 . .
C C8 0.34720(15) 0.7613(3) 0.5707(3) 0.0382(7) Uani d 1 . .
H H8 0.374195 0.803323 0.515422 0.046 Uiso calc 1 . .
C C6 0.33381(16) 1.1786(3) 0.4739(3) 0.0359(6) Uani d 1 . .
C C13 0.21653(15) 0.8708(3) 0.7865(3) 0.0383(7) Uani d 1 . .
H H13A 0.243062 0.955166 0.824815 0.046 Uiso calc 1 . .
H H13B 0.206067 0.816317 0.861507 0.046 Uiso calc 1 . .
C C9 0.34871(16) 0.6146(3) 0.5877(3) 0.0447(8) Uani d 1 . .
H H9 0.377768 0.559121 0.546037 0.054 Uiso calc 1 . .
C C5 0.38298(18) 1.2604(3) 0.4257(3) 0.0430(7) Uani d 1 . .
H H5 0.366991 1.328721 0.358405 0.052 Uiso calc 1 . .
C C4 0.45510(18) 1.2404(3) 0.4774(3) 0.0459(8) Uani d 1 . .
H H4 0.488229 1.292653 0.442936 0.055 Uiso calc 1 . .
C C3 0.47873(16) 1.1423(3) 0.5811(3) 0.0408(7) Uani d 1 . .
H H3 0.527698 1.129421 0.617432 0.049 Uiso calc 1 . .
C C11 0.26455(17) 0.6344(3) 0.7292(3) 0.0436(8) Uani d 1 . .
H H11 0.236429 0.590723 0.781473 0.052 Uiso calc 1 . .
C C10 0.30743(18) 0.5508(3) 0.6661(3) 0.0488(8) Uani d 1 . .
H H10 0.308209 0.452307 0.676839 0.059 Uiso calc 1 . .
C C16 0.06160(19) 0.3234(3) 0.4609(4) 0.0515(8) Uani d 1 . .
H H16A 0.020800 0.385304 0.426179 0.062 Uiso calc 1 . .
H H16B 0.088673 0.314490 0.390895 0.062 Uiso calc 1 . .
C C15 0.1082(2) 0.3869(4) 0.5871(4) 0.0593(10) Uani d 1 . .
H H15A 0.152356 0.332453 0.614785 0.071 Uiso calc 1 . .
H H15B 0.120699 0.483999 0.568925 0.071 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
H1WA O1W H1WB . . 104.5 ?
C1 N1 C7 . . 124.4(2) ?
C1 N1 H1 . . 117.8 ?
C7 N1 H1 . . 117.8 ?
C16 N2 H2A . . 109.5 ?
C16 N2 H2B . . 109.5 ?
H2A N2 H2B . . 109.5 ?
C16 N2 H2C . . 109.5 ?
H2A N2 H2C . . 109.5 ?
H2B N2 H2C . . 109.5 ?
C15 O3 H3A . . 109.5 ?
C3 C2 C1 . . 122.1(3) ?
C3 C2 Cl1 . . 117.0(2) ?
C1 C2 Cl1 . . 120.9(2) ?
O2 C14 O1 . . 123.9(3) ?
O2 C14 C13 . . 118.9(3) ?
O1 C14 C13 . . 117.2(3) ?
C6 C1 N1 . . 121.1(3) ?
C6 C1 C2 . . 115.9(3) ?
N1 C1 C2 . . 122.8(3) ?
C11 C12 C7 . . 118.5(3) ?
C11 C12 C13 . . 120.4(3) ?
C7 C12 C13 . . 121.1(3) ?
C8 C7 C12 . . 119.7(3) ?
C8 C7 N1 . . 121.6(3) ?
C12 C7 N1 . . 118.7(3) ?
C9 C8 C7 . . 120.4(3) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C5 C6 C1 . . 122.5(3) ?
C5 C6 Cl2 . . 118.4(2) ?
C1 C6 Cl2 . . 119.1(2) ?
C12 C13 C14 . . 112.7(2) ?
C12 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
C12 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C10 C9 C8 . . 120.3(3) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C4 C5 C6 . . 119.8(3) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C4 C3 . . 120.0(3) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C3 C2 . . 119.5(3) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C10 C11 C12 . . 121.4(3) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C9 C10 C11 . . 119.6(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
N2 C16 C15 . . 110.0(3) ?
N2 C16 H16A . . 109.7 ?
C15 C16 H16A . . 109.7 ?
N2 C16 H16B . . 109.7 ?
C15 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
O3 C15 C16 . . 109.2(3) ?
O3 C15 H15A . . 109.8 ?
C16 C15 H15A . . 109.8 ?
O3 C15 H15B . . 109.8 ?
C16 C15 H15B . . 109.8 ?
H15A C15 H15B . . 108.3 ?
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
Cl1 C2 . 1.734(3) ?
Cl2 C6 . 1.741(3) ?
O1 C14 . 1.259(3) ?
O1W H1WA . 0.8501 ?
O1W H1WB . 0.8504 ?
N1 C1 . 1.396(3) ?
N1 C7 . 1.410(3) ?
N1 H1 . 0.8600 ?
O2 C14 . 1.248(3) ?
N2 C16 . 1.486(4) ?
N2 H2A . 0.8900 ?
N2 H2B . 0.8900 ?
N2 H2C . 0.8900 ?
O3 C15 . 1.412(4) ?
O3 H3A . 0.8200 ?
C2 C3 . 1.389(4) ?
C2 C1 . 1.400(4) ?
C14 C13 . 1.523(4) ?
C1 C6 . 1.394(4) ?
C12 C11 . 1.395(4) ?
C12 C7 . 1.403(4) ?
C12 C13 . 1.508(4) ?
C7 C8 . 1.398(4) ?
C8 C9 . 1.387(4) ?
C8 H8 . 0.9300 ?
C6 C5 . 1.387(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C9 C10 . 1.377(4) ?
C9 H9 . 0.9300 ?
C5 C4 . 1.368(5) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.384(4) ?
C4 H4 . 0.9300 ?
C3 H3 . 0.9300 ?
C11 C10 . 1.391(5) ?
C11 H11 . 0.9300 ?
C10 H10 . 0.9300 ?
C16 C15 . 1.494(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
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
N1 H1 O1 . 0.86 2.27 2.884(3) 128.9 yes
N2 H2A O2 3_566 0.89 1.96 2.811(4) 160.2 yes
N2 H2B O1W 2_546 0.89 2.15 2.947(4) 148.1 yes
N2 H2C O1 1_545 0.89 1.92 2.802(3) 169.2 yes
O3 H3A O1W . 0.82 1.96 2.770(4) 167.5 yes
O1W H1WB O2 . 0.85 1.87 2.690(3) 161.4 yes
O1W H1WA O1 4_576 0.85 2.00 2.809(3) 157.6 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
C7 N1 C1 C6 . . . . 131.3(3) ?
C7 N1 C1 C2 . . . . -52.7(4) ?
C3 C2 C1 C6 . . . . -4.4(4) ?
Cl1 C2 C1 C6 . . . . 174.1(2) ?
C3 C2 C1 N1 . . . . 179.4(3) ?
Cl1 C2 C1 N1 . . . . -2.1(4) ?
C11 C12 C7 C8 . . . . 0.9(4) ?
C13 C12 C7 C8 . . . . -179.4(3) ?
C11 C12 C7 N1 . . . . -179.8(3) ?
C13 C12 C7 N1 . . . . -0.1(4) ?
C1 N1 C7 C8 . . . . -16.6(4) ?
C1 N1 C7 C12 . . . . 164.1(3) ?
C12 C7 C8 C9 . . . . -2.0(4) ?
N1 C7 C8 C9 . . . . 178.7(3) ?
N1 C1 C6 C5 . . . . 179.3(3) ?
C2 C1 C6 C5 . . . . 3.0(4) ?
N1 C1 C6 Cl2 . . . . -0.6(4) ?
C2 C1 C6 Cl2 . . . . -176.9(2) ?
C11 C12 C13 C14 . . . . -100.2(3) ?
C7 C12 C13 C14 . . . . 80.1(3) ?
O2 C14 C13 C12 . . . . 117.9(3) ?
O1 C14 C13 C12 . . . . -61.2(4) ?
C7 C8 C9 C10 . . . . 1.8(4) ?
C1 C6 C5 C4 . . . . 0.3(5) ?
Cl2 C6 C5 C4 . . . . -179.8(2) ?
C6 C5 C4 C3 . . . . -2.4(5) ?
C5 C4 C3 C2 . . . . 0.9(5) ?
C1 C2 C3 C4 . . . . 2.6(4) ?
Cl1 C2 C3 C4 . . . . -176.0(2) ?
C7 C12 C11 C10 . . . . 0.3(4) ?
C13 C12 C11 C10 . . . . -179.3(3) ?
C8 C9 C10 C11 . . . . -0.5(5) ?
C12 C11 C10 C9 . . . . -0.5(5) ?
N2 C16 C15 O3 . . . . -53.2(4) ?

_cod_database_fobs_code 1566904
