#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/95/2229580.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_2229580
loop_
_publ_author_name
'Shi, Lu'
'Zhang, Qin'
'Xiao, Qi'
'Wu, Tao'
'Zhu, Hong-Jun'
_publ_section_title
;
 2-(2-Chlorophenoxy)benzoic acid
;
_journal_coeditor_code           BQ2280
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o748
_journal_paper_doi               10.1107/S1600536811006301
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H9 Cl O3'
_chemical_formula_moiety         'C13 H9 Cl O3'
_chemical_formula_sum            'C13 H9 Cl O3'
_chemical_formula_weight         248.65
_chemical_name_systematic
;
2-(2-Chlorophenoxy)benzoic 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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9930(14)
_cell_length_b                   24.986(5)
_cell_length_c                   7.5140(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      9
_cell_volume                     1182.1(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0882
_diffrn_reflns_av_sigmaI/netI    0.1084
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4651
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_correction_T_min  0.9115
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                1061
_reflns_number_total             2177
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2280.cif
_cod_data_source_block           I
_cod_original_cell_volume        1182.1(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229580
_cod_database_fobs_code          2229580
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_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.30495(19) 0.80926(6) 0.11968(19) 0.1627(6) Uani d . 1 . .
O O1 0.5536(3) 0.90532(7) 0.1714(2) 0.0654(6) Uani d . 1 . .
C C1 0.5689(5) 0.81539(15) 0.2793(5) 0.0820(9) Uani d . 1 . .
O O2 0.0554(3) 0.99730(8) -0.2082(2) 0.0756(6) Uani d . 1 . .
H H2B -0.0220 1.0088 -0.1606 0.113 Uiso calc R 1 . .
C C2 0.6811(8) 0.77525(16) 0.4047(6) 0.1038(13) Uani d . 1 . .
H H2A 0.6136 0.7432 0.4050 0.125 Uiso calc R 1 . .
O O3 0.2120(3) 0.96137(9) 0.0872(2) 0.0780(7) Uani d . 1 . .
C C3 0.8874(8) 0.78149(18) 0.5273(6) 0.1116(16) Uani d . 1 . .
H H3A 0.9597 0.7542 0.6150 0.134 Uiso calc R 1 . .
C C4 0.9925(6) 0.82717(19) 0.5254(5) 0.0998(13) Uani d . 1 . .
H H4A 1.1367 0.8308 0.6076 0.120 Uiso calc R 1 . .
C C5 0.8814(5) 0.86787(13) 0.3997(4) 0.0701(9) Uani d . 1 . .
H H5A 0.9506 0.8994 0.3967 0.084 Uiso calc R 1 . .
C C6 0.6706(5) 0.86214(12) 0.2799(3) 0.0533(7) Uani d . 1 . .
C C7 0.5230(4) 0.91164(10) -0.0195(3) 0.0499(7) Uani d . 1 . .
C C8 0.3564(4) 0.94517(10) -0.1407(3) 0.0492(7) Uani d . 1 . .
C C9 0.3345(4) 0.95491(11) -0.3322(3) 0.0608(8) Uani d . 1 . .
H H9A 0.2275 0.9778 -0.4143 0.073 Uiso calc R 1 . .
C C10 0.4647(5) 0.93199(13) -0.4018(4) 0.0755(9) Uani d . 1 . .
H H10A 0.4463 0.9388 -0.5299 0.091 Uiso calc R 1 . .
C C11 0.6243(5) 0.89853(13) -0.2802(4) 0.0760(10) Uani d . 1 . .
H H11A 0.7140 0.8826 -0.3268 0.091 Uiso calc R 1 . .
C C12 0.6529(4) 0.88827(11) -0.0903(3) 0.0619(8) Uani d . 1 . .
H H12A 0.7608 0.8654 -0.0099 0.074 Uiso calc R 1 . .
C C13 0.2020(4) 0.96877(11) -0.0801(3) 0.0492(6) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C6 . . 119.41(19) ?
C2 C1 C6 . . 118.9(3) ?
C2 C1 Cl . . 122.5(3) ?
C6 C1 Cl . . 118.6(3) ?
C13 O2 H2B . . 109.5 ?
C3 C2 C1 . . 120.8(4) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
C2 C3 C4 . . 121.0(4) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
C3 C4 C5 . . 118.8(4) ?
C3 C4 H4A . . 120.6 ?
C5 C4 H4A . . 120.6 ?
C6 C5 C4 . . 120.2(3) ?
C6 C5 H5A . . 119.9 ?
C4 C5 H5A . . 119.9 ?
C5 C6 C1 . . 120.3(3) ?
C5 C6 O1 . . 120.0(3) ?
C1 C6 O1 . . 119.4(3) ?
O1 C7 C12 . . 122.2(2) ?
O1 C7 C8 . . 117.3(2) ?
C12 C7 C8 . . 120.5(2) ?
C9 C8 C7 . . 117.4(2) ?
C9 C8 C13 . . 118.9(2) ?
C7 C8 C13 . . 123.7(2) ?
C10 C9 C8 . . 122.0(3) ?
C10 C9 H9A . . 119.0 ?
C8 C9 H9A . . 119.0 ?
C9 C10 C11 . . 119.1(2) ?
C9 C10 H10A . . 120.4 ?
C11 C10 H10A . . 120.4 ?
C10 C11 C12 . . 120.8(3) ?
C10 C11 H11A . . 119.6 ?
C12 C11 H11A . . 119.6 ?
C7 C12 C11 . . 120.2(2) ?
C7 C12 H12A . . 119.9 ?
C11 C12 H12A . . 119.9 ?
O3 C13 O2 . . 121.3(2) ?
O3 C13 C8 . . 122.0(2) ?
O2 C13 C8 . . 116.7(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
Cl C1 . 1.716(3) ?
O1 C7 . 1.364(3) ?
O1 C6 . 1.385(3) ?
C1 C2 . 1.366(4) ?
C1 C6 . 1.367(4) ?
O2 C13 . 1.276(3) ?
O2 H2B . 0.8200 ?
C2 C3 . 1.341(5) ?
C2 H2A . 0.9300 ?
O3 C13 . 1.242(2) ?
C3 C4 . 1.361(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.375(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.360(3) ?
C5 H5A . 0.9300 ?
C7 C12 . 1.367(3) ?
C7 C8 . 1.402(3) ?
C8 C9 . 1.401(3) ?
C8 C13 . 1.466(3) ?
C9 C10 . 1.358(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.376(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.376(3) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
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
O2 H2B O3 3_575 0.82 1.81 2.621(3) 172
C11 H11A Cg1 1_554 0.93 2.74 3.582(4) 151
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
C6 C1 C2 C3 . . . . 0.3(5) ?
Cl C1 C2 C3 . . . . 179.9(3) ?
C1 C2 C3 C4 . . . . -2.4(6) ?
C2 C3 C4 C5 . . . . 2.2(6) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
C4 C5 C6 C1 . . . . -1.8(4) ?
C4 C5 C6 O1 . . . . 172.1(2) ?
C2 C1 C6 C5 . . . . 1.7(4) ?
Cl C1 C6 C5 . . . . -177.9(2) ?
C2 C1 C6 O1 . . . . -172.3(3) ?
Cl C1 C6 O1 . . . . 8.1(4) ?
C7 O1 C6 C5 . . . . 95.1(3) ?
C7 O1 C6 C1 . . . . -90.9(3) ?
C6 O1 C7 C12 . . . . -21.0(4) ?
C6 O1 C7 C8 . . . . 161.5(2) ?
O1 C7 C8 C9 . . . . 175.4(2) ?
C12 C7 C8 C9 . . . . -2.2(4) ?
O1 C7 C8 C13 . . . . -6.7(4) ?
C12 C7 C8 C13 . . . . 175.8(2) ?
C7 C8 C9 C10 . . . . 1.7(4) ?
C13 C8 C9 C10 . . . . -176.4(3) ?
C8 C9 C10 C11 . . . . -0.5(5) ?
C9 C10 C11 C12 . . . . -0.1(5) ?
O1 C7 C12 C11 . . . . -175.8(3) ?
C8 C7 C12 C11 . . . . 1.6(4) ?
C10 C11 C12 C7 . . . . -0.4(5) ?
C9 C8 C13 O3 . . . . 179.5(3) ?
C7 C8 C13 O3 . . . . 1.7(4) ?
C9 C8 C13 O2 . . . . -0.2(4) ?
C7 C8 C13 O2 . . . . -178.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4295573
