##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     ' SHELXL97 (Sheldrick, 2008)'
_journal_date_recd_electronic     2015-06-03
_journal_date_accepted     2015-06-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      8
_journal_page_first     931
_journal_page_last     933
_journal_paper_category     GM
_journal_paper_doi     10.1107/S2056989015012633
_journal_coeditor_code     WM5173
_publ_contact_author_name     'Dr Graham Smith'
_publ_contact_author_address
;
    Science and Engineering Faculty
    Queensland University of Technology
    GPO Box 2434, Brisbane, Queensland 4001,
    Australia
;
_publ_contact_author_email     g.smith@qut.edu.au
_publ_contact_author_fax     ' 61 7 3138 1804 '
_publ_contact_author_phone     ' 61 7 3300 2667 '
_publ_section_title
;
Crystal structure of poly[[di-μ₂-aqua-aquasodium]
4-amino-3,5,6-trichloropyridine-2-carboxylate trihydrate], the sodium salt of
the herbicide picloram
;
loop_
    _publ_author_name
    _publ_author_address
    ' Graham Smith '
;
  Science and Engineering Faculty
  Queensland University of Technology
  GPO Box 2434, Brisbane, Queensland 4001,
  Australia
;
_publ_section_synopsis
;
The trihydrated sodium salt of the herbicide picloram comprises a cationic
μ₂-aqua-bridged chain structure that is linked to the picloramate anions
through amine N---H...O and water O---H...O and O---H...N hydrogen bonds.
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 1409779'
_chemical_name_systematic
;
Poly[[di-μ₂-aqua-aquasodium]
4-amino-3,5,6-trichloropyridine-2-carboxylate trihydrate]
;
_chemical_name_common     'sodium picloramate hexahydrate'
_chemical_formula_moiety     'C6 H2 Cl3 N2 O2 +, H6 Na O3 -, 3(H2 O)'
_chemical_formula_sum     'C6 H14 Cl3 N2 Na O8'
_chemical_formula_iupac     '[Na (H2 O)3] (C6 H2 Cl3 N2 O2), 3H2 O'
_chemical_formula_weight     371.53
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.5625(5)
_cell_length_b     8.4574(6)
_cell_length_c     13.8553(10)
_cell_angle_alpha     78.747(6)
_cell_angle_beta     79.374(6)
_cell_angle_gamma     88.864(6)
_cell_volume     741.17(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2548
_cell_measurement_theta_min     3.75
_cell_measurement_theta_max     28.8
_cell_measurement_temperature     200(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.665
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     380
_exptl_absorpt_coefficient_mu     0.682
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_absorpt_correction_T_min     0.947
_exptl_absorpt_correction_T_max     0.980
_exptl_special_details
;
;
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.077
_diffrn_reflns_number     6040
_diffrn_reflns_av_R_equivalents     0.0246
_diffrn_reflns_av_sigmaI/netI     0.0363
_diffrn_reflns_theta_min     3.25
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2905
_reflns_number_gt     2487
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0394
_refine_ls_R_factor_gt     0.0306
_refine_ls_wR_factor_gt     0.0818
_refine_ls_wR_factor_ref     0.0879
_refine_ls_goodness_of_fit_ref     1.001
_refine_ls_restrained_S_all     1.001
_refine_ls_number_reflns     2905
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0478P)²+0.2264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.299
_refine_diff_density_min     -0.280
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_refine_ls_extinction_coef     0.050(3)
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'
    'Na' 'Na' 0.0362 0.0249
                         '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'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SIR92 (Altomare et al., 1993)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl3 0.73580(8) 0.09272(5) 0.52593(4) 0.0257(2) Uani d . 1.000 . .
    Cl Cl5 0.76678(8) 0.74102(5) 0.46993(4) 0.0240(2) Uani d . 1.000 . .
    Cl Cl6 0.67863(9) 0.70381(6) 0.70472(4) 0.0295(2) Uani d . 1.000 . .
    O O21 0.4767(2) 0.04778(17) 0.77535(11) 0.0287(5) Uani d . 1.000 . .
    O O22 0.8188(2) 0.04407(17) 0.77067(11) 0.0292(5) Uani d . 1.000 . .
    N N1 0.6684(2) 0.39495(18) 0.71307(12) 0.0196(5) Uani d . 1.000 . .
    N N4 0.7849(3) 0.42747(19) 0.40294(12) 0.0213(5) Uani d . 1.000 . .
    C C2 0.6814(3) 0.2631(2) 0.67196(14) 0.0172(5) Uani d . 1.000 . .
    C C3 0.7193(3) 0.2696(2) 0.57064(14) 0.0170(5) Uani d . 1.000 . .
    C C4 0.7473(3) 0.4178(2) 0.50250(14) 0.0168(6) Uani d . 1.000 . .
    C C5 0.7335(3) 0.5539(2) 0.54712(14) 0.0173(5) Uani d . 1.000 . .
    C C6 0.6946(3) 0.5361(2) 0.64975(15) 0.0186(6) Uani d . 1.000 . .
    C C21 0.6561(3) 0.1034(2) 0.74534(14) 0.0204(6) Uani d . 1.000 . .
    Na Na1 0.24455(12) 0.42819(9) 1.01558(6) 0.0268(3) Uani d . 1.000 . .
    O O1W 0.0817(2) 0.53070(17) 0.87914(10) 0.0299(5) Uani d . 1.000 . .
    O O2W 0.1503(2) 0.15728(17) 1.05390(11) 0.0300(5) Uani d . 1.000 . .
    O O3W 0.4202(2) 0.62279(17) 1.07140(10) 0.0272(5) Uani d . 1.000 . .
    O O4W 0.1371(2) 0.27585(17) 0.77676(12) 0.0317(5) Uani d . 1.000 . .
    O O5W 0.2700(2) -0.10534(18) 0.95986(11) 0.0325(5) Uani d . 1.000 . .
    O O6W 0.1709(2) 0.82429(17) 0.73270(11) 0.0298(5) Uani d . 1.000 . .
    H H41 0.80460 0.32820 0.37840 0.0260 Uiso d R 1.000 . .
    H H42 0.80680 0.53330 0.36040 0.0260 Uiso d R 1.000 . .
    H H11W 0.09740 0.45450 0.85000 0.0450 Uiso d R 1.000 . .
    H H12W 0.10510 0.62480 0.83710 0.0450 Uiso d R 1.000 . .
    H H21W 0.15180 0.09520 1.11820 0.0450 Uiso d R 1.000 . .
    H H22W 0.19310 0.08550 1.02150 0.0450 Uiso d R 1.000 . .
    H H31W 0.38250 0.71930 1.04480 0.0410 Uiso d R 1.000 . .
    H H32W 0.40980 0.61800 1.13770 0.0410 Uiso d R 1.000 . .
    H H41W 0.02360 0.20490 0.77150 0.0480 Uiso d R 1.000 . .
    H H42W 0.25100 0.20920 0.77350 0.0480 Uiso d R 1.000 . .
    H H51W 0.34890 -0.07030 0.89970 0.0490 Uiso d R 1.000 . .
    H H52W 0.15590 -0.13130 0.93860 0.18(2) Uiso d R 1.000 . .
    H H61W 0.06160 0.89510 0.72480 0.0450 Uiso d R 1.000 . .
    H H62W 0.30130 0.87260 0.72460 0.0450 Uiso d R 1.000 . .
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
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
    Na1 O1W . 2_567 2.4185(16) yes
    Na1 O3W . 2_667 2.3803(16) yes
    Na1 O1W . . 2.3529(16) yes
    Na1 O2W . . 2.3183(17) yes
    Na1 O3W . . 2.3530(16) yes
    Cl3 C3 . . 1.7216(18) no
    Cl5 C5 . . 1.7213(18) no
    Cl6 C6 . . 1.7289(19) no
    O21 C21 . . 1.243(2) no
    O22 C21 . . 1.250(2) no
    O1W H12W . . 0.8900 no
    O1W H11W . . 0.8200 no
    O2W H21W . . 0.9400 no
    O2W H22W . . 0.8400 no
    O3W H31W . . 0.8800 no
    O3W H32W . . 0.9000 no
    O4W H42W . . 0.9300 no
    O4W H41W . . 0.9900 no
    O5W H52W . . 0.9000 no
    O5W H51W . . 0.9000 no
    O6W H61W . . 0.9300 no
    O6W H62W . . 0.9300 no
    N1 C2 . . 1.342(2) no
    N1 C6 . . 1.330(2) no
    N4 C4 . . 1.342(2) no
    N4 H41 . . 0.9600 no
    N4 H42 . . 0.9700 no
    C2 C3 . . 1.370(3) no
    C2 C21 . . 1.515(3) no
    C3 C4 . . 1.407(3) no
    C4 C5 . . 1.403(2) no
    C5 C6 . . 1.376(3) no
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
    O1W Na1 O3W 2_567 . 2_667 173.66(6) no
    O1W Na1 O3W . . . 114.69(6) no
    O1W Na1 O1W . . 2_567 86.32(5) no
    O1W Na1 O3W . . 2_667 100.02(6) no
    O2W Na1 O3W . . . 141.97(6) no
    O1W Na1 O2W 2_567 . . 85.88(6) no
    O2W Na1 O3W . . 2_667 92.71(6) no
    O1W Na1 O2W . . . 103.20(6) no
    O3W Na1 O3W . . 2_667 84.24(5) no
    O1W Na1 O3W 2_567 . . 93.06(5) no
    Na1 O1W Na1 . . 2_567 93.68(5) no
    Na1 O3W Na1 . . 2_667 95.76(6) no
    Na1 O1W H11W . . . 100.00 no
    Na1 O1W H11W 2_567 . . 121.00 no
    Na1 O1W H12W . . . 128.00 no
    H11W O1W H12W . . . 112.00 no
    Na1 O1W H12W 2_567 . . 103.00 no
    Na1 O2W H22W . . . 128.00 no
    H21W O2W H22W . . . 97.00 no
    Na1 O2W H21W . . . 121.00 no
    Na1 O3W H32W . . . 119.00 no
    H31W O3W H32W . . . 108.00 no
    Na1 O3W H31W . . . 109.00 no
    Na1 O3W H32W 2_667 . . 115.00 no
    Na1 O3W H31W 2_667 . . 109.00 no
    H41W O4W H42W . . . 103.00 no
    H51W O5W H52W . . . 98.00 no
    H61W O6W H62W . . . 116.00 no
    C2 N1 C6 . . . 116.35(16) no
    C4 N4 H41 . . . 118.00 no
    C4 N4 H42 . . . 118.00 no
    H41 N4 H42 . . . 124.00 no
    N1 C2 C3 . . . 123.14(17) no
    N1 C2 C21 . . . 115.53(16) no
    C3 C2 C21 . . . 121.32(16) no
    Cl3 C3 C2 . . . 119.28(14) no
    Cl3 C3 C4 . . . 119.39(14) no
    C2 C3 C4 . . . 121.32(16) no
    N4 C4 C3 . . . 122.49(16) no
    N4 C4 C5 . . . 122.95(17) no
    C3 C4 C5 . . . 114.55(17) no
    Cl5 C5 C4 . . . 118.07(14) no
    Cl5 C5 C6 . . . 121.71(14) no
    C4 C5 C6 . . . 120.22(16) no
    Cl6 C6 N1 . . . 115.37(15) no
    Cl6 C6 C5 . . . 120.21(14) no
    N1 C6 C5 . . . 124.42(17) no
    O21 C21 O22 . . . 127.24(18) no
    O21 C21 C2 . . . 116.83(17) no
    O22 C21 C2 . . . 115.91(17) 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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O3W Na1 O3W Na1 2_667 . . 2_667 0.00(6) no
    O1W Na1 O1W Na1 . . 2_567 2_567 0.00(6) no
    O2W Na1 O1W Na1 . . 2_567 2_567 -103.53(6) no
    O3W Na1 O1W Na1 . . 2_567 2_567 114.57(6) no
    O1W Na1 O3W Na1 . . 2_667 2_667 114.11(6) no
    O2W Na1 O3W Na1 . . 2_667 2_667 -141.98(6) no
    O3W Na1 O3W Na1 . . 2_667 2_667 -0.02(8) no
    O2W Na1 O3W Na1 . . . 2_667 87.03(10) no
    O1W Na1 O3W Na1 2_567 . . 2_667 174.25(5) no
    O2W Na1 O1W Na1 . . . 2_567 84.89(6) no
    O3W Na1 O1W Na1 . . . 2_567 -91.68(6) no
    O1W Na1 O1W Na1 2_567 . . 2_567 0.00(5) no
    O3W Na1 O1W Na1 2_667 . . 2_567 -179.91(5) no
    O1W Na1 O3W Na1 . . . 2_667 -98.40(6) no
    C6 N1 C2 C21 . . . . 178.63(17) no
    C2 N1 C6 Cl6 . . . . -179.62(14) no
    C6 N1 C2 C3 . . . . 0.0(3) no
    C2 N1 C6 C5 . . . . -0.1(3) no
    C21 C2 C3 C4 . . . . -178.59(18) no
    N1 C2 C21 O21 . . . . 89.1(2) no
    N1 C2 C3 Cl3 . . . . 179.26(15) no
    N1 C2 C3 C4 . . . . 0.0(3) no
    C21 C2 C3 Cl3 . . . . 0.7(3) no
    C3 C2 C21 O22 . . . . 89.4(2) no
    N1 C2 C21 O22 . . . . -89.3(2) no
    C3 C2 C21 O21 . . . . -92.2(2) no
    C2 C3 C4 C5 . . . . 0.1(3) no
    Cl3 C3 C4 N4 . . . . 0.6(3) no
    Cl3 C3 C4 C5 . . . . -179.13(15) no
    C2 C3 C4 N4 . . . . 179.9(2) no
    C3 C4 C5 Cl5 . . . . 179.71(15) no
    N4 C4 C5 Cl5 . . . . -0.1(3) no
    N4 C4 C5 C6 . . . . -180.0(2) no
    C3 C4 C5 C6 . . . . -0.2(3) no
    C4 C5 C6 N1 . . . . 0.2(3) no
    Cl5 C5 C6 Cl6 . . . . -0.2(3) no
    Cl5 C5 C6 N1 . . . . -179.72(15) no
    C4 C5 C6 Cl6 . . . . 179.74(16) 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 O4W . 0.82 1.97 2.786(2) 178 yes
    O1W H12W O6W . 0.89 1.99 2.877(2) 174 yes
    O2W H21W O22 2_657 0.94 1.79 2.721(2) 171 yes
    O2W H22W O5W . 0.84 1.98 2.816(2) 172 yes
    O3W H31W O5W 1_565 0.88 1.93 2.781(2) 163 yes
    O3W H32W N1 2_667 0.90 2.02 2.910(2) 170 yes
    O4W H41W O22 1_455 0.99 1.93 2.916(2) 173 yes
    O4W H42W O21 . 0.93 1.99 2.918(2) 174 yes
    O5W H51W O21 . 0.90 1.87 2.748(2) 166 yes
    O5W H52W O2W 2_557 0.90 2.01 2.8481(19) 155 yes
    O6W H61W O22 1_465 0.93 2.10 2.972(2) 156 yes
    O6W H62W Cl6 . 0.93 2.83 3.4400(15) 124 no
    O6W H62W O21 1_565 0.93 2.19 2.996(2) 144 yes
    N4 H41 Cl3 . 0.96 2.54 2.9956(17) 109 no
    N4 H41 O6W 2_666 0.96 2.18 3.080(2) 156 yes
    N4 H42 Cl5 . 0.97 2.52 2.9690(17) 108 no
    N4 H42 O4W 2_666 0.97 2.22 3.146(2) 160 yes
