#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239836.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_2239836
loop_
_publ_author_name
'Cho, Seonghwa'
'Kim, Jineun'
'Jeon, Youngeun'
'Kim, Tae Ho'
_publ_section_title
;
 Crystal structure of triclopyr
;
_journal_coeditor_code           ZS2309
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o940
_journal_paper_doi               10.1107/S160053681401681X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C7 H4 Cl3 N O3'
_chemical_formula_moiety         'C7 H4 Cl3 N O3'
_chemical_formula_sum            'C7 H4 Cl3 N O3'
_chemical_formula_weight         256.46
_chemical_name_common            triclopyr
_chemical_name_systematic
;
2-[(3,5,6-Trichloropyridin-2-yl)oxy]acetic acid
;
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 106.261(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5771(9)
_cell_length_b                   25.409(3)
_cell_length_c                   10.1668(12)
_cell_measurement_reflns_used    3761
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.24
_cell_volume                     1879.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2010)'
_computing_publication_material  'SHELXTL (Brandenburg, 2010)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3699
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_correction_T_min  0.6477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0441
_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)+(0.0219P)²+2.0682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                3080
_reflns_number_total             3699
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2309sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239836
_cod_database_fobs_code          2239836
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 0.66278(13) 0.53311(3) 0.94222(8) 0.0336(2) Uani d . 1 1
Cl Cl2 0.86627(14) 0.62564(3) 1.13208(9) 0.0397(2) Uani d . 1 1
Cl Cl3 0.67175(14) 0.75251(3) 0.69082(10) 0.0408(2) Uani d . 1 1
Cl Cl4 1.00995(14) 0.31553(3) 0.50221(9) 0.0380(2) Uani d . 1 1
Cl Cl5 0.79593(15) 0.23214(3) 0.28102(10) 0.0432(3) Uani d . 1 1
Cl Cl6 0.66657(14) 0.38875(3) -0.09150(8) 0.0403(2) Uani d . 1 1
O O1 0.4722(3) 0.65825(8) 0.5624(2) 0.0317(5) Uani d . 1 1
O O2 0.6886(3) 0.58941(10) 0.4787(3) 0.0386(6) Uani d . 1 1
O O3 0.4491(3) 0.53970(9) 0.3695(3) 0.0382(6) Uani d . 1 1
H H3O 0.5290 0.5231 0.3434 0.057 Uiso calc R 1 1
O O4 0.9075(3) 0.44645(8) 0.1341(2) 0.0315(5) Uani d . 1 1
O O5 0.9552(3) 0.54570(9) 0.3905(2) 0.0316(5) Uani d . 1 1
H H5O 0.8784 0.5599 0.4250 0.047 Uiso calc R 1 1
O O6 0.7219(3) 0.49064(9) 0.2971(3) 0.0361(6) Uani d . 1 1
N N1 0.5733(4) 0.60258(10) 0.7479(3) 0.0248(6) Uani d . 1 1
N N2 0.9432(4) 0.38215(10) 0.3000(3) 0.0258(6) Uani d . 1 1
C C1 0.6641(4) 0.59584(11) 0.8776(3) 0.0242(7) Uani d . 1 1
C C2 0.7565(5) 0.63593(12) 0.9613(3) 0.0267(7) Uani d . 1 1
C C3 0.7598(5) 0.68502(11) 0.9024(3) 0.0278(7) Uani d . 1 1
H H3 0.8254 0.7133 0.9552 0.033 Uiso calc R 1 1
C C4 0.6673(5) 0.69213(11) 0.7674(3) 0.0254(7) Uani d . 1 1
C C5 0.5714(4) 0.64974(12) 0.6938(3) 0.0241(7) Uani d . 1 1
C C6 0.3859(5) 0.61313(13) 0.4863(3) 0.0331(8) Uani d . 1 1
H H6A 0.2905 0.6247 0.4032 0.040 Uiso calc R 1 1
H H6B 0.3251 0.5920 0.5430 0.040 Uiso calc R 1 1
C C7 0.5265(5) 0.57983(12) 0.4455(3) 0.0283(7) Uani d . 1 1
C C8 0.9176(5) 0.33276(12) 0.3324(3) 0.0266(7) Uani d . 1 1
C C9 0.8219(5) 0.29661(12) 0.2378(3) 0.0276(7) Uani d . 1 1
C C10 0.7423(5) 0.31367(12) 0.1045(3) 0.0279(7) Uani d . 1 1
H H10 0.6717 0.2901 0.0376 0.033 Uiso calc R 1 1
C C11 0.7668(5) 0.36496(12) 0.0706(3) 0.0266(7) Uani d . 1 1
C C12 0.8738(4) 0.39780(11) 0.1722(3) 0.0255(7) Uani d . 1 1
C C13 1.0054(5) 0.48192(12) 0.2385(3) 0.0301(8) Uani d . 1 1
H H13A 1.0624 0.5100 0.1967 0.036 Uiso calc R 1 1
H H13B 1.1048 0.4627 0.3053 0.036 Uiso calc R 1 1
C C14 0.8768(5) 0.50619(12) 0.3117(3) 0.0269(7) Uani d . 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
C5 O1 C6 116.6(2)
C7 O3 H3O 109.5
C12 O4 C13 117.9(2)
C14 O5 H5O 109.5
C1 N1 C5 118.6(3)
C12 N2 C8 119.0(3)
N1 C1 C2 123.5(3)
N1 C1 Cl1 116.4(2)
C2 C1 Cl1 120.1(2)
C1 C2 C3 117.6(3)
C1 C2 Cl2 121.7(2)
C3 C2 Cl2 120.7(2)
C4 C3 C2 119.1(3)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 118.7(3)
C3 C4 Cl3 120.1(2)
C5 C4 Cl3 121.2(2)
N1 C5 O1 119.7(3)
N1 C5 C4 122.4(3)
O1 C5 C4 117.9(3)
O1 C6 C7 110.3(3)
O1 C6 H6A 109.6
C7 C6 H6A 109.6
O1 C6 H6B 109.6
C7 C6 H6B 109.6
H6A C6 H6B 108.1
O2 C7 O3 125.0(3)
O2 C7 C6 123.6(3)
O3 C7 C6 111.3(3)
N2 C8 C9 122.8(3)
N2 C8 Cl4 116.2(2)
C9 C8 Cl4 120.9(2)
C8 C9 C10 118.1(3)
C8 C9 Cl5 122.1(3)
C10 C9 Cl5 119.7(2)
C11 C10 C9 119.3(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C12 118.1(3)
C10 C11 Cl6 121.3(3)
C12 C11 Cl6 120.5(2)
N2 C12 O4 120.4(3)
N2 C12 C11 122.5(3)
O4 C12 C11 117.0(3)
O4 C13 C14 110.5(3)
O4 C13 H13A 109.6
C14 C13 H13A 109.6
O4 C13 H13B 109.6
C14 C13 H13B 109.6
H13A C13 H13B 108.1
O6 C14 O5 125.5(3)
O6 C14 C13 122.9(3)
O5 C14 C13 111.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.725(3)
Cl2 C2 1.722(3)
Cl3 C4 1.725(3)
Cl4 C8 1.728(3)
Cl5 C9 1.721(3)
Cl6 C11 1.720(3)
O1 C5 1.354(4)
O1 C6 1.434(4)
O2 C7 1.204(4)
O3 C7 1.314(4)
O3 H3O 0.8400
O4 C12 1.341(4)
O4 C13 1.431(4)
O5 C14 1.318(4)
O5 H5O 0.8400
O6 C14 1.208(4)
N1 C1 1.317(4)
N1 C5 1.317(4)
N2 C12 1.319(4)
N2 C8 1.325(4)
C1 C2 1.385(4)
C2 C3 1.387(4)
C3 C4 1.367(4)
C3 H3 0.9500
C4 C5 1.394(4)
C6 C7 1.507(5)
C6 H6A 0.9900
C6 H6B 0.9900
C8 C9 1.379(4)
C9 C10 1.389(4)
C10 C11 1.374(4)
C10 H10 0.9500
C11 C12 1.397(4)
C13 C14 1.513(5)
C13 H13A 0.9900
C13 H13B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3O O6 0.84 1.85 2.688(3) 174
O5 H5O O2 0.84 1.84 2.671(3) 172
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
C5 N1 C1 C2 0.8(5)
C5 N1 C1 Cl1 -179.5(2)
N1 C1 C2 C3 -3.1(5)
Cl1 C1 C2 C3 177.2(2)
N1 C1 C2 Cl2 177.6(3)
Cl1 C1 C2 Cl2 -2.1(4)
C1 C2 C3 C4 2.3(5)
Cl2 C2 C3 C4 -178.4(3)
C2 C3 C4 C5 0.5(5)
C2 C3 C4 Cl3 -179.1(3)
C1 N1 C5 O1 -177.0(3)
C1 N1 C5 C4 2.3(5)
C6 O1 C5 N1 -4.9(4)
C6 O1 C5 C4 175.7(3)
C3 C4 C5 N1 -3.0(5)
Cl3 C4 C5 N1 176.6(2)
C3 C4 C5 O1 176.4(3)
Cl3 C4 C5 O1 -4.1(4)
C5 O1 C6 C7 -75.3(3)
O1 C6 C7 O2 3.1(5)
O1 C6 C7 O3 -176.7(3)
C12 N2 C8 C9 0.3(5)
C12 N2 C8 Cl4 -179.1(2)
N2 C8 C9 C10 -3.0(5)
Cl4 C8 C9 C10 176.4(2)
N2 C8 C9 Cl5 178.1(3)
Cl4 C8 C9 Cl5 -2.5(4)
C8 C9 C10 C11 2.3(5)
Cl5 C9 C10 C11 -178.8(3)
C9 C10 C11 C12 0.8(5)
C9 C10 C11 Cl6 -178.3(2)
C8 N2 C12 O4 -175.5(3)
C8 N2 C12 C11 3.1(5)
C13 O4 C12 N2 -5.8(4)
C13 O4 C12 C11 175.5(3)
C10 C11 C12 N2 -3.6(5)
Cl6 C11 C12 N2 175.5(2)
C10 C11 C12 O4 175.0(3)
Cl6 C11 C12 O4 -5.9(4)
C12 O4 C13 C14 -80.9(3)
O4 C13 C14 O6 11.0(4)
O4 C13 C14 O5 -168.6(2)
