#------------------------------------------------------------------------------
#$Date: 2018-08-07 17:33:59 +0300 (Tue, 07 Aug 2018) $
#$Revision: 209447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/98/2019804.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_2019804
loop_
_publ_author_name
'Smith, Graham'
_publ_section_title
;
 Low-dimensional coordination polymeric structures in alkali metal complex
 salts of the herbicide (2,4-dichlorophenoxy)acetic acid (2,4-D)
;
_journal_coeditor_code           KY3071
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961500056X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Li (C8 H5 Cl2 O3) (H2 O)], 2H2 O'
_chemical_formula_moiety         'C8 H7 Cl2 Li O4, 2(H2 O)'
_chemical_formula_sum            'C8 H11 Cl2 Li O6'
_chemical_formula_weight         281.01
_chemical_name_common
'lithium (2,4-dichlorophenoxy)acetate trihydrate'
_chemical_name_systematic
'Poly[[aqua[μ₃-2-(2,4-dichlorophenoxy)acetato-κ³O¹:O¹:O^1'^:]lithium(I)] dihydrate]'
_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                90.00
_cell_angle_beta                 90.343(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8705(4)
_cell_length_b                   4.9984(3)
_cell_length_c                   30.9367(17)
_cell_measurement_reflns_used    2663
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      3.96
_cell_volume                     1217.03(12)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution
;
SIR92 (Altomare et al., 1993)
;
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            7126
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0269P)²+0.6487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                2108
_reflns_number_total             2391
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ky3071sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Removing duplicate rows from the ATOM_TYPE loop.

 Antanas Vaitkus,
 2018-08-07
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019804
_cod_database_fobs_code          2019804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl2 1.27919(6) -0.12915(9) 0.589110(10) 0.0329(2) Uani d . 1.000
Cl Cl4 0.69450(7) -0.32482(12) 0.50398(2) 0.0482(2) Uani d . 1.000
O O1W 0.53927(17) -0.1305(3) 0.68571(4) 0.0315(4) Uani d D 1.000
O O11 1.09103(16) 0.2868(2) 0.63187(4) 0.0282(4) Uani d . 1.000
O O13 0.91847(14) 0.0867(2) 0.70030(4) 0.0234(4) Uani d . 1.000
O O14 0.82594(15) 0.4876(2) 0.72053(4) 0.0238(4) Uani d . 1.000
C C1 0.9901(2) 0.1520(3) 0.60290(5) 0.0233(5) Uani d . 1.000
C C2 1.0678(2) -0.0509(3) 0.57930(5) 0.0232(5) Uani d . 1.000
C C3 0.9783(2) -0.1965(4) 0.54875(6) 0.0283(5) Uani d . 1.000
C C4 0.8087(2) -0.1391(4) 0.54187(6) 0.0311(6) Uani d . 1.000
C C5 0.7290(2) 0.0595(4) 0.56468(6) 0.0344(6) Uani d . 1.000
C C6 0.8202(2) 0.2046(4) 0.59526(6) 0.0328(6) Uani d . 1.000
C C12 1.0111(2) 0.4701(3) 0.66080(6) 0.0280(5) Uani d . 1.000
C C13 0.9095(2) 0.3348(3) 0.69635(5) 0.0188(5) Uani d . 1.000
Li Li1 0.7439(4) -0.1484(5) 0.72192(9) 0.0227(8) Uani d . 1.000
O O2W 0.47121(19) 0.3859(3) 0.64621(5) 0.0407(5) Uani d D 1.000
O O3W 1.23705(18) -0.0636(3) 0.73011(5) 0.0357(4) Uani d D 1.000
H H3 1.03270 -0.33390 0.53270 0.0340 Uiso c R 1.000
H H5 0.61230 0.09750 0.55960 0.0410 Uiso c R 1.000
H H6 0.76500 0.34180 0.61110 0.0390 Uiso c R 1.000
H H11W 0.446(2) -0.115(5) 0.6995(7) 0.0470 Uiso d D 1.000
H H12W 0.523(3) -0.279(4) 0.6722(7) 0.0470 Uiso d D 1.000
H H121 0.93430 0.58810 0.64400 0.0340 Uiso c R 1.000
H H122 1.09950 0.58420 0.67430 0.0340 Uiso c R 1.000
H H21W 0.374(2) 0.359(5) 0.6351(8) 0.0610 Uiso d D 1.000
H H22W 0.498(3) 0.233(4) 0.6570(8) 0.0610 Uiso d D 1.000
H H31W 1.141(2) -0.038(5) 0.7176(7) 0.0530 Uiso d D 1.000
H H32W 1.233(3) -0.213(4) 0.7433(8) 0.0530 Uiso d D 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'
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'
Li Li -0.0003 0.0001 '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
O1W Li1 O14 . 1_545 107.71(14) no
O1W Li1 O14 . 2_646 105.43(15) no
O1W Li1 O13 . . 111.01(14) no
O13 Li1 O14 . 2_646 107.67(13) no
O14 Li1 O14 1_545 2_646 115.90(14) no
O13 Li1 O14 . 1_545 109.09(16) no
Li1 O14 Li1 1_565 2_656 102.01(13) no
Li1 O1W H11W . . 115.1(14) no
Li1 O1W H12W . . 111.0(15) no
C1 O11 C12 . . 117.96(13) no
C13 O13 Li1 . . 126.78(13) no
C13 O14 Li1 . 1_565 139.60(14) no
C13 O14 Li1 . 2_656 118.28(12) no
H11W O1W H12W . . 101(2) no
H21W O2W H22W . . 104(2) no
H31W O3W H32W . . 108(2) no
O11 C1 C2 . . 116.48(14) no
C2 C1 C6 . . 118.44(15) no
O11 C1 C6 . . 125.07(15) no
Cl2 C2 C3 . . 119.03(12) no
Cl2 C2 C1 . . 119.75(12) no
C1 C2 C3 . . 121.20(15) no
C2 C3 C4 . . 118.96(17) no
C3 C4 C5 . . 121.04(17) no
Cl4 C4 C5 . . 119.76(13) no
Cl4 C4 C3 . . 119.20(15) no
C4 C5 C6 . . 119.49(15) no
C1 C6 C5 . . 120.86(17) no
O11 C12 C13 . . 113.75(12) no
O13 C13 O14 . . 125.08(15) no
O13 C13 C12 . . 118.85(14) no
O14 C13 C12 . . 116.03(13) no
C2 C3 H3 . . 121.00 no
C4 C3 H3 . . 121.00 no
C4 C5 H5 . . 120.00 no
C6 C5 H5 . . 120.00 no
C5 C6 H6 . . 120.00 no
C1 C6 H6 . . 120.00 no
O11 C12 H122 . . 109.00 no
C13 C12 H121 . . 109.00 no
C13 C12 H122 . . 109.00 no
H121 C12 H122 . . 108.00 no
O11 C12 H121 . . 109.00 no
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
Li1 O1W . 1.958(3) no
Li1 O13 . 1.931(3) no
Li1 O14 1_545 1.931(3) no
Li1 O14 2_646 1.986(3) no
Cl2 C2 . 1.7341(16) no
Cl4 C4 . 1.7409(19) no
O11 C1 . 1.371(2) no
O11 C12 . 1.429(2) no
O13 C13 . 1.2481(18) no
O14 C13 . 1.2575(19) no
O1W H11W . 0.855(18) no
O1W H12W . 0.86(2) no
O2W H21W . 0.848(18) no
O2W H22W . 0.86(2) no
O3W H32W . 0.85(2) no
O3W H31W . 0.857(17) no
C1 C6 . 1.382(2) no
C1 C2 . 1.393(2) no
C2 C3 . 1.382(2) no
C3 C4 . 1.381(2) no
C4 C5 . 1.372(3) no
C5 C6 . 1.389(3) no
C12 C13 . 1.522(2) no
C3 H3 . 0.9500 no
C5 H5 . 0.9500 no
C6 H6 . 0.9500 no
C12 H121 . 0.9900 no
C12 H122 . 0.9900 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
O1W H11W O3W 1_455 0.855(18) 1.920(18) 2.774(2) 178(2) yes
O1W H12W O2W 1_545 0.86(2) 1.90(2) 2.760(2) 175(2) yes
O2W H21W O11 1_455 0.848(18) 2.258(16) 3.063(2) 159(2) yes
O2W H22W O1W . 0.86(2) 2.05(2) 2.904(2) 174(2) yes
O3W H31W O13 . 0.857(17) 1.932(17) 2.7702(18) 166(2) yes
O3W H32W O3W 2_746 0.85(2) 1.95(2) 2.793(2) 170(2) yes
C6 H6 O2W . 0.95 2.5700 3.302(2) 134 no
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 O11 C1 C2 . . . -171.51(13) no
C12 O11 C1 C6 . . . 9.3(2) no
C1 O11 C12 C13 . . . 72.75(17) no
Li1 O13 C13 O14 . . . 31.9(3) no
Li1 O13 C13 C12 . . . -150.39(16) no
C13 O13 Li1 O1W . . . 61.1(2) no
C13 O13 Li1 O14 . . 1_545 179.59(14) no
C13 O13 Li1 O14 . . 2_646 -53.9(2) no
Li1 O14 C13 O13 1_565 . . -166.17(18) no
Li1 O14 C13 C12 1_565 . . 16.1(3) no
Li1 O14 C13 O13 2_656 . . 18.3(2) no
Li1 O14 C13 C12 2_656 . . -159.49(14) no
C13 O14 Li1 O1W . 1_565 1_565 79.5(2) no
C13 O14 Li1 O13 . 1_565 1_565 -41.1(3) no
C13 O14 Li1 O14 . 1_565 2_656 -162.81(17) no
C13 O14 Li1 O14 . 2_656 2_646 -41.9(2) no
C13 O14 Li1 O1W . 2_656 2_656 77.12(17) no
C13 O14 Li1 O13 . 2_656 2_656 -164.31(13) no
O11 C1 C2 Cl2 . . . 2.6(2) no
O11 C1 C2 C3 . . . -178.98(15) no
C6 C1 C2 Cl2 . . . -178.14(13) no
C6 C1 C2 C3 . . . 0.3(2) no
O11 C1 C6 C5 . . . 178.96(16) no
C2 C1 C6 C5 . . . -0.2(3) no
Cl2 C2 C3 C4 . . . 178.14(14) no
C1 C2 C3 C4 . . . -0.3(3) no
C2 C3 C4 Cl4 . . . -179.11(14) no
C2 C3 C4 C5 . . . 0.2(3) no
Cl4 C4 C5 C6 . . . 179.16(15) no
C3 C4 C5 C6 . . . -0.2(3) no
C4 C5 C6 C1 . . . 0.2(3) no
O11 C12 C13 O13 . . . 7.5(2) no
O11 C12 C13 O14 . . . -174.58(14) no
