#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011891.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_2011891
loop_
_publ_author_name
'Castellari, Carlo'
'Comelli, Fabio'
'Ottani, Stefano'
_publ_section_title
;
 Anti-inflammatory drugs. IX. Hydrated diethylammonium
 [2-(2,6-dichlorophenylamino)phenyl]acetate
 (HDEA·D·H₂O)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              437
_journal_page_last               438
_journal_paper_doi               10.1107/S010827010002076X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C4 H12 N 1+, C14 H10 Cl2 N O2 1-, H2 O'
_chemical_formula_moiety         'C4 H12 N 1+, C14 H10 Cl2 N O2 1-, H2 O'
_chemical_formula_sum            'C18 H24 Cl2 N2 O3'
_chemical_formula_weight         387.29
_chemical_name_systematic
;
Diethylammonium [2-(2,6-dichlorophenylamino)phenyl]acetate hydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.544(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7490(10)
_cell_length_b                   12.2960(10)
_cell_length_c                   14.5910(10)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.45
_cell_volume                     2009.9(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Bruker SMART 2000 CDD'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0837
_diffrn_reflns_av_sigmaI/netI    .0586
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26140
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 20
_diffrn_standards_number         112
_exptl_absorpt_coefficient_mu    .341
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         .268
_refine_diff_density_min         -.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   .900
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         5882
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      .898
_refine_ls_restrained_S_obs      1.046
_refine_ls_R_factor_all          .097
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          -.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0776P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .146
_refine_ls_wR_factor_ref         .121
_reflns_number_gt                3025
_reflns_number_total             5884
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1485.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2011891
_cod_database_fobs_code          2011891
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_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
_atom_site_disorder_group
_atom_site_type_symbol
O3W .37858(14) .36066(13) .05331(13) .0705(4) Uani d D 1 . O
H1W .4022(19) .4078(16) .0898(14) .065(7) Uiso d D 1 . H
H2W .417(2) .353(2) .0161(16) .089(9) Uiso d D 1 . H
N2 .24273(15) .17862(15) .06555(12) .0628(5) Uani d D 1 . N
H11 .1704(18) .1806(16) .0167(14) .069(6) Uiso d D 1 . H
H12 .2904(19) .2386(17) .0596(15) .082(7) Uiso d D 1 . H
C17 .2162(3) .1836(3) .1587(2) .0938(9) Uani d D 1 . C
H13 .2895 .1738 .2110 .113 Uiso calc R 1 . H
H14 .1621 .1251 .1618 .113 Uiso calc R 1 . H
C18 .1613(3) .2898(3) .1699(2) .1103(11) Uani d DU 1 . C
H15 .2157 .3476 .1685 .128(4) Uiso calc R 1 . H
H16 .1440 .2911 .2302 .128(4) Uiso calc R 1 . H
H17 .0886 .2993 .1183 .128(4) Uiso calc R 1 . H
C15 .3127(2) .0806(2) .0526(2) .0920(9) Uani d D 1 . C
H18 .3871 .0776 .1046 .110 Uiso calc R 1 . H
H19 .2677 .0153 .0557 .110 Uiso calc R 1 . H
C16 .3392(3) .0839(2) -.0416(2) .0989(9) Uani d DU 1 . C
H20 .3833 .0200 -.0479 .128(4) Uiso calc R 1 . H
H21 .3856 .1475 -.0441 .128(4) Uiso calc R 1 . H
H22 .2656 .0862 -.0932 .128(4) Uiso calc R 1 . H
Cl1 .49102(5) .30953(5) .34141(5) .0761(2) Uani d D 1 . Cl
Cl2 .75567(4) .63886(4) .54114(4) .0665(2) Uani d D 1 . Cl
N1 .62960(12) .51678(13) .36216(10) .0483(4) Uani d . 1 . N
H1 .568(2) .5098(17) .3138(16) .075(7) Uiso d . 1 . H
C1 .73342(14) .53617(13) .33572(11) .0426(4) Uani d D 1 . C
C2 .72775(14) .61209(13) .26303(12) .0443(4) Uani d D 1 . C
C3 .8304(2) .6286(2) .23471(14) .0556(5) Uani d D 1 . C
H2 .8275 .6769 .18501 .067 Uiso calc RD 1 . H
C4 .9357(2) .5746(2) .2791(2) .0656(6) Uani d D 1 . C
H3 1.0029 .5869 .2594 .079 Uiso calc RD 1 . H
C5 .9411(2) .5033(2) .3519(2) .0631(5) Uani d D 1 . C
H4 1.0127 .4686 .3828 .076 Uiso calc RD 1 . H
C6 .8404(2) .4823(2) .38003(13) .0542(4) Uani d D 1 . C
H5 .8442 .4321 .42858 .065 Uiso calc RD 1 . H
C7 .63058(14) .46594(13) .44787(12) .0442(4) Uani d D 1 . C
C8 .56979(15) .36909(14) .45045(14) .0517(4) Uani d D 1 . C
C9 .5697(2) .3203(2) .5358(2) .0675(6) Uani d D 1 . C
H6 .5281 .2558 .5351 .081 Uiso calc RD 1 . H
C10 .6314(2) .3678(2) .6218(2) .0707(6) Uani d D 1 . C
H7 .6329 .3344 .6794 .085 Uiso calc RD 1 . H
C11 .6905(2) .4638(2) .62313(14) .0623(5) Uani d D 1 . C
H8 .7318 .4961 .68133 .075 Uiso calc RD 1 . H
C12 .68864(14) .51274(15) .53720(12) .0491(4) Uani d D 1 . C
C13 .6175(2) .67962(15) .22115(13) .0520(4) Uani d D 1 . C
H9 .6395 .74371 .19163 .062 Uiso calc RD 1 . H
H10 .5884 .70406 .27323 .062 Uiso calc RD 1 . H
C14 .5153(2) .6220(2) .14635(12) .0516(4) Uani d . 1 . C
O1 .47567(14) .53628(13) .16993(10) .0760(5) Uani d . 1 . O
O2 .47698(12) .66754(13) .06538(9) .0699(4) Uani d . 1 . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
H1W O3W H2W 113(3) ?
C17 N2 C15 114.9(2) ?
C17 N2 H11 107.8(13) ?
C15 N2 H11 109.5(13) ?
C17 N2 H12 110.2(13) ?
C15 N2 H12 104.6(14) ?
H11 N2 H12 109.8(18) ?
N2 C17 C18 110.7(2) ?
N2 C17 H13 109.49(13) ?
C18 C17 H13 109.49(15) ?
N2 C17 H14 109.49(12) ?
C18 C17 H14 109.49(15) ?
H13 C17 H14 108.1 ?
C17 C18 H15 109.47(15) ?
C17 C18 H16 109.47(14) ?
H15 C18 H16 109.5 ?
C17 C18 H17 109.47(15) ?
H15 C18 H17 109.5 ?
H16 C18 H17 109.5 ?
C16 C15 N2 111.5(2) ?
C16 C15 H18 109.32(14) ?
N2 C15 H18 109.32(11) ?
C16 C15 H19 109.32(14) ?
N2 C15 H19 109.32(11) ?
H18 C15 H19 108.0 ?
C15 C16 H20 109.47(14) ?
C15 C16 H21 109.47(14) ?
H20 C16 H21 109.5 ?
C15 C16 H22 109.47(14) ?
H20 C16 H22 109.5 ?
H21 C16 H22 109.5 ?
C7 N1 C1 123.27(14) ?
C7 N1 H1 118.3(15) ?
C1 N1 H1 112.5(15) ?
C6 C1 C2 119.9(2) ?
C6 C1 N1 121.8(2) ?
C2 C1 N1 118.30(14) ?
C1 C2 C3 118.1(2) ?
C1 C2 C13 120.9(2) ?
C3 C2 C13 120.8(2) ?
C4 C3 C2 121.4(2) ?
C4 C3 H2 119.32(12) ?
C2 C3 H2 119.32(11) ?
C5 C4 C3 119.9(2) ?
C5 C4 H3 120.03(11) ?
C3 C4 H3 120.03(12) ?
C4 C5 C6 120.4(2) ?
C4 C5 H4 119.80(11) ?
C6 C5 H4 119.80(12) ?
C5 C6 C1 120.2(2) ?
C5 C6 H5 119.89(12) ?
C1 C6 H5 119.89(11) ?
C8 C7 N1 122.7(2) ?
C8 C7 C12 115.8(2) ?
N1 C7 C12 121.4(2) ?
C9 C8 C7 122.3(2) ?
C9 C8 Cl1 119.7(2) ?
C7 C8 Cl1 118.00(14) ?
C10 C9 C8 119.6(2) ?
C10 C9 H6 120.19(13) ?
C8 C9 H6 120.19(13) ?
C11 C10 C9 120.3(2) ?
C11 C10 H7 119.84(12) ?
C9 C10 H7 119.84(13) ?
C10 C11 C12 119.6(2) ?
C10 C11 H8 120.22(12) ?
C12 C11 H8 120.22(12) ?
C11 C12 C7 122.3(2) ?
C11 C12 Cl2 118.4(2) ?
C7 C12 Cl2 119.21(13) ?
C2 C13 C14 115.36(15) ?
C2 C13 H9 108.43(10) ?
C14 C13 H9 108.43(10) ?
C2 C13 H10 108.43(10) ?
C14 C13 H10 108.43(10) ?
H9 C13 H10 107.5 ?
O1 C14 O2 125.4(2) y
O1 C14 C13 118.3(2) ?
O2 C14 C13 116.3(2) ?
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
O3W H1W . .78(2) ?
O3W H2W . .81(2) ?
N2 C17 . 1.485(3) y
N2 C15 . 1.502(3) y
N2 H11 . .93(2) ?
N2 H12 . .95(2) ?
C17 C18 . 1.488(4) ?
C17 H13 . .97 ?
C17 H14 . .97 ?
C18 H15 . .96 ?
C18 H16 . .96 ?
C18 H17 . .96 ?
C15 C16 . 1.499(4) ?
C15 H18 . .97 ?
C15 H19 . .97 ?
C16 H20 . .96 ?
C16 H21 . .96 ?
C16 H22 . .96 ?
Cl1 C8 . 1.743(2) ?
Cl2 C12 . 1.732(2) ?
N1 C7 . 1.395(2) ?
N1 C1 . 1.406(2) ?
N1 H1 . .85(2) ?
C1 C6 . 1.395(2) ?
C1 C2 . 1.399(2) ?
C2 C3 . 1.403(2) ?
C2 C13 . 1.505(2) ?
C3 C4 . 1.381(3) ?
C3 H2 . .93 ?
C4 C5 . 1.363(3) ?
C4 H3 . .93 ?
C5 C6 . 1.389(3) ?
C5 H4 . .93 ?
C6 H5 . .93 ?
C7 C8 . 1.395(2) ?
C7 C12 . 1.400(2) ?
C8 C9 . 1.382(3) ?
C9 C10 . 1.377(3) ?
C9 H6 . .93 ?
C10 C11 . 1.367(3) ?
C10 H7 . .93 ?
C11 C12 . 1.385(3) ?
C11 H8 . .93 ?
C13 C14 . 1.531(2) ?
C13 H9 . .97 ?
C13 H10 . .97 ?
C14 O1 . 1.242(2) y
C14 O2 . 1.261(2) y
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 H1 Cl1 . .85(2) 2.69(2) 2.990(2) 102(2)
N1 H1 O1 . .85(2) 2.08(2) 2.853(2) 151(2)
O3W H1W O1 . .78(2) 2.00(2) 2.773(2) 172(2)
O3W H2W O2 3_665 .81(2) 1.98(2) 2.788(2) 175(3)
N2 H11 O2 2_545 .93(2) 1.79(2) 2.713(2) 170(2)
N2 H12 O3W . .95(2) 1.84(2) 2.786(2) 176(2)
C5 H4 Cl2 3_766 .93 2.93 3.851(2) 173
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
_geom_torsion_publ_flag
C15 N2 C17 C18 172.5(2) ?
C17 N2 C15 C16 -178.1(2) ?
C7 N1 C1 C6 16.8(3) y
C7 N1 C1 C2 -163.0(2) ?
C6 C1 C2 C3 2.2(2) ?
N1 C1 C2 C3 -177.96(15) ?
C6 C1 C2 C13 -173.7(2) ?
N1 C1 C2 C13 6.1(2) ?
C1 C2 C3 C4 -2.2(3) ?
C13 C2 C3 C4 173.7(2) ?
C2 C3 C4 C5 .2(3) ?
C3 C4 C5 C6 1.8(3) ?
C4 C5 C6 C1 -1.7(3) ?
C2 C1 C6 C5 -.4(3) ?
N1 C1 C6 C5 179.8(2) ?
C1 N1 C7 C8 -119.8(2) ?
C1 N1 C7 C12 63.4(2) y
N1 C7 C8 C9 -178.9(2) ?
C12 C7 C8 C9 -1.9(2) ?
N1 C7 C8 Cl1 .6(2) ?
C12 C7 C8 Cl1 177.63(12) ?
C7 C8 C9 C10 -.1(3) ?
Cl1 C8 C9 C10 -179.66(15) ?
C8 C9 C10 C11 1.4(3) ?
C9 C10 C11 C12 -.5(3) ?
C10 C11 C12 C7 -1.7(3) ?
C10 C11 C12 Cl2 175.62(15) ?
C8 C7 C12 C11 2.8(2) ?
N1 C7 C12 C11 179.9(2) ?
C8 C7 C12 Cl2 -174.50(12) ?
N1 C7 C12 Cl2 2.5(2) ?
C1 C2 C13 C14 -79.5(2) ?
C3 C2 C13 C14 104.7(2) ?
C2 C13 C14 O1 56.8(2) ?
C2 C13 C14 O2 -124.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135304
