#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230508.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_2230508
loop_
_publ_author_name
'Xu, Jia-Ying'
'Cheng, Wei-Hua'
'Zhu, Xun'
'Gu, Dong-ya'
_publ_section_title
;
 2-(o-Tolyloxy)benzoic acid
;
_journal_coeditor_code           VM2093
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1394
_journal_paper_doi               10.1107/S1600536811017119
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H12 O3'
_chemical_formula_moiety         'C14 H12 O3'
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.24
_chemical_name_common
;
2-(o-tolyloxy)benzoic acid
;
_chemical_name_systematic
;
2-(o-Tolyloxy)benzoic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.34(3)
_cell_angle_beta                 96.36(3)
_cell_angle_gamma                115.76(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0900(14)
_cell_length_b                   7.4820(15)
_cell_length_c                   12.680(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      9
_cell_volume                     594.5(3)
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2382
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0550
_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)+(0.1000P)²+0.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                1437
_reflns_number_total             2190
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            vm2093.cif
_cod_data_source_block           I
_cod_original_cell_volume        594.5(2)
_cod_database_code               2230508
_cod_database_fobs_code          2230508
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4820(3) 0.1177(2) 0.80889(14) 0.0712(5) Uani d . 1 1 . .
C C1 0.2152(6) 0.0560(7) 0.6153(4) 0.1589(19) Uani d . 1 1 . .
H H1A 0.1796 -0.0054 0.6782 0.238 Uiso calc R 1 1 . .
H H1B 0.1718 -0.0467 0.5539 0.238 Uiso calc R 1 1 . .
H H1C 0.1434 0.1376 0.6043 0.238 Uiso calc R 1 1 . .
O O2 0.0651(3) -0.2020(3) 0.99961(15) 0.0772(6) Uani d . 1 1 . .
H H2A -0.0042 -0.1483 1.0230 0.116 Uiso calc R 1 1 . .
C C2 0.4515(5) 0.1851(4) 0.6302(2) 0.0833(8) Uani d . 1 1 . .
O O3 0.1733(3) 0.0598(3) 0.91609(17) 0.0833(6) Uani d . 1 1 . .
C C3 0.5551(8) 0.2950(7) 0.5531(3) 0.1137(13) Uani d . 1 1 . .
H H3A 0.4763 0.2862 0.4874 0.136 Uiso calc R 1 1 . .
C C4 0.7687(8) 0.4147(6) 0.5719(3) 0.1119(13) Uani d . 1 1 . .
H H4A 0.8334 0.4873 0.5196 0.134 Uiso calc R 1 1 . .
C C5 0.8863(5) 0.4283(5) 0.6654(3) 0.0904(9) Uani d . 1 1 . .
H H5A 1.0323 0.5095 0.6776 0.108 Uiso calc R 1 1 . .
C C6 0.7915(4) 0.3231(4) 0.7426(2) 0.0666(7) Uani d . 1 1 . .
H H6A 0.8727 0.3321 0.8075 0.080 Uiso calc R 1 1 . .
C C7 0.5773(4) 0.2046(3) 0.72433(19) 0.0570(6) Uani d . 1 1 . .
C C8 0.4571(3) -0.0695(3) 0.82224(18) 0.0533(6) Uani d . 1 1 . .
C C9 0.5732(4) -0.1542(3) 0.7750(2) 0.0654(7) Uani d . 1 1 . .
H H9A 0.6639 -0.0868 0.7289 0.078 Uiso calc R 1 1 . .
C C10 0.5543(5) -0.3372(4) 0.7963(2) 0.0735(7) Uani d . 1 1 . .
H H10A 0.6318 -0.3935 0.7642 0.088 Uiso calc R 1 1 . .
C C11 0.4216(4) -0.4382(4) 0.8646(2) 0.0722(7) Uani d . 1 1 . .
H H11A 0.4096 -0.5619 0.8791 0.087 Uiso calc R 1 1 . .
C C12 0.3066(4) -0.3541(3) 0.91134(19) 0.0605(6) Uani d . 1 1 . .
H H12A 0.2185 -0.4218 0.9583 0.073 Uiso calc R 1 1 . .
C C13 0.3188(3) -0.1708(3) 0.89020(17) 0.0497(5) Uani d . 1 1 . .
C C14 0.1800(3) -0.0953(3) 0.93742(18) 0.0522(5) 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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C7 . . 119.48(17) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C14 O2 H2A . . 109.5 ?
C7 C2 C3 . . 116.0(3) ?
C7 C2 C1 . . 120.1(3) ?
C3 C2 C1 . . 123.9(3) ?
C4 C3 C2 . . 121.5(3) ?
C4 C3 H3A . . 119.2 ?
C2 C3 H3A . . 119.2 ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C4 C5 C6 . . 119.9(3) ?
C4 C5 H5A . . 120.1 ?
C6 C5 H5A . . 120.1 ?
C5 C6 C7 . . 119.8(3) ?
C5 C6 H6A . . 120.1 ?
C7 C6 H6A . . 120.1 ?
C2 C7 C6 . . 122.3(2) ?
C2 C7 O1 . . 118.9(2) ?
C6 C7 O1 . . 118.4(2) ?
O1 C8 C9 . . 121.8(2) ?
O1 C8 C13 . . 117.77(18) ?
C9 C8 C13 . . 120.32(19) ?
C10 C9 C8 . . 120.0(2) ?
C10 C9 H9A . . 120.0 ?
C8 C9 H9A . . 120.0 ?
C9 C10 C11 . . 120.6(2) ?
C9 C10 H10A . . 119.7 ?
C11 C10 H10A . . 119.7 ?
C10 C11 C12 . . 119.3(2) ?
C10 C11 H11A . . 120.4 ?
C12 C11 H11A . . 120.4 ?
C11 C12 C13 . . 121.7(2) ?
C11 C12 H12A . . 119.1 ?
C13 C12 H12A . . 119.1 ?
C12 C13 C8 . . 118.0(2) ?
C12 C13 C14 . . 118.97(19) ?
C8 C13 C14 . . 123.02(18) ?
O3 C14 O2 . . 122.0(2) ?
O3 C14 C13 . . 122.05(19) ?
O2 C14 C13 . . 115.94(18) ?
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
O1 C8 . 1.363(2) ?
O1 C7 . 1.392(3) ?
C1 C2 . 1.505(5) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
O2 C14 . 1.272(2) ?
O2 H2A . 0.8200 ?
C2 C7 . 1.364(4) ?
C2 C3 . 1.398(5) ?
O3 C14 . 1.235(2) ?
C3 C4 . 1.361(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.340(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.363(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.364(3) ?
C6 H6A . 0.9300 ?
C8 C9 . 1.390(3) ?
C8 C13 . 1.393(3) ?
C9 C10 . 1.372(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.375(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.376(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.390(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.482(3) ?
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
O2 H2A O3 2_557 0.82 1.81 2.624(3) 172 yes
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
C7 C2 C3 C4 . . . . -0.3(5) ?
C1 C2 C3 C4 . . . . 177.9(4) ?
C2 C3 C4 C5 . . . . 0.7(6) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
C4 C5 C6 C7 . . . . -0.1(4) ?
C3 C2 C7 C6 . . . . -0.3(4) ?
C1 C2 C7 C6 . . . . -178.6(3) ?
C3 C2 C7 O1 . . . . 172.8(2) ?
C1 C2 C7 O1 . . . . -5.5(4) ?
C5 C6 C7 C2 . . . . 0.5(4) ?
C5 C6 C7 O1 . . . . -172.7(2) ?
C8 O1 C7 C2 . . . . 94.5(3) ?
C8 O1 C7 C6 . . . . -92.1(3) ?
C7 O1 C8 C9 . . . . 18.4(3) ?
C7 O1 C8 C13 . . . . -165.1(2) ?
O1 C8 C9 C10 . . . . 175.6(2) ?
C13 C8 C9 C10 . . . . -0.9(4) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C9 C10 C11 C12 . . . . 0.3(4) ?
C10 C11 C12 C13 . . . . 0.9(4) ?
C11 C12 C13 C8 . . . . -2.0(4) ?
C11 C12 C13 C14 . . . . 175.9(2) ?
O1 C8 C13 C12 . . . . -174.58(19) ?
C9 C8 C13 C12 . . . . 2.0(3) ?
O1 C8 C13 C14 . . . . 7.6(3) ?
C9 C8 C13 C14 . . . . -175.9(2) ?
C12 C13 C14 O3 . . . . -175.2(2) ?
C8 C13 C14 O3 . . . . 2.6(4) ?
C12 C13 C14 O2 . . . . 3.5(3) ?
C8 C13 C14 O2 . . . . -178.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 203158
