#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/11/2231142.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_2231142
loop_
_publ_author_name
'Zhang, Zhi-Fang'
_publ_section_title
;
 2-(m-Tolyloxy)benzoic acid
;
_journal_coeditor_code           HG5059
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1935
_journal_paper_doi               10.1107/S1600536811026171
_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_systematic
;
2-(m-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                94.28(3)
_cell_angle_beta                 97.50(3)
_cell_angle_gamma                102.54(3)
_cell_formula_units_Z            2
_cell_length_a                   5.1930(10)
_cell_length_b                   7.8000(16)
_cell_length_c                   14.868(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     579.5(2)
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2387
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0521
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1132
_reflns_number_total             2132
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg5059.cif
_cod_data_source_block           I
_cod_database_code               2231142
_cod_database_fobs_code          2231142
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
O O1 0.3075(4) 0.93730(19) 0.80140(11) 0.0780(6) Uani d . 1 1
C C1 0.1740(8) 0.8008(4) 0.4694(2) 0.1111(12) Uani d . 1 1
H H1A 0.3613 0.8039 0.4758 0.167 Uiso calc R 1 1
H H1B 0.1429 0.9087 0.4479 0.167 Uiso calc R 1 1
H H1C 0.0778 0.7027 0.4264 0.167 Uiso calc R 1 1
O O2 0.7293(3) 0.95411(19) 0.92424(11) 0.0683(6) Uani d . 1 1
C C2 0.0798(7) 0.7808(3) 0.56045(19) 0.0694(8) Uani d . 1 1
O O3 0.9363(3) 1.21756(19) 0.99325(11) 0.0706(6) Uani d . 1 1
H H3B 1.0355 1.1598 1.0172 0.106 Uiso calc R 1 1
C C3 0.2341(6) 0.8720(3) 0.63921(19) 0.0660(8) Uani d . 1 1
H H3A 0.3994 0.9455 0.6366 0.079 Uiso calc R 1 1
C C4 0.1428(6) 0.8542(3) 0.72192(19) 0.0617(8) Uani d . 1 1
C C5 -0.0968(6) 0.7484(3) 0.7283(2) 0.0720(8) Uani d . 1 1
H H5A -0.1568 0.7396 0.7844 0.086 Uiso calc R 1 1
C C6 -0.2495(6) 0.6544(4) 0.6507(2) 0.0856(10) Uani d . 1 1
H H6A -0.4126 0.5789 0.6539 0.103 Uiso calc R 1 1
C C7 -0.1597(7) 0.6725(4) 0.5675(2) 0.0826(10) Uani d . 1 1
H H7A -0.2652 0.6092 0.5151 0.099 Uiso calc R 1 1
C C8 0.3485(5) 1.1181(3) 0.81945(15) 0.0519(7) Uani d . 1 1
C C9 0.1781(5) 1.2089(3) 0.77587(16) 0.0640(8) Uani d . 1 1
H H9A 0.0352 1.1490 0.7324 0.077 Uiso calc R 1 1
C C10 0.2199(6) 1.3888(3) 0.79684(17) 0.0673(8) Uani d . 1 1
H H10A 0.1049 1.4500 0.7672 0.081 Uiso calc R 1 1
C C11 0.4270(6) 1.4776(3) 0.86027(17) 0.0671(8) Uani d . 1 1
H H11A 0.4544 1.5992 0.8737 0.081 Uiso calc R 1 1
C C12 0.5958(5) 1.3877(3) 0.90456(16) 0.0580(7) Uani d . 1 1
H H12A 0.7366 1.4495 0.9482 0.070 Uiso calc R 1 1
C C13 0.5610(5) 1.2048(3) 0.88546(14) 0.0459(6) Uani d . 1 1
C C14 0.7462(5) 1.1132(3) 0.93547(15) 0.0488(6) 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
C8 O1 C4 118.75(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
C7 C2 C3 118.2(3)
C7 C2 C1 121.2(3)
C3 C2 C1 120.7(3)
C14 O3 H3B 109.5
C2 C3 C4 119.9(3)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 121.6(3)
C5 C4 O1 118.9(3)
C3 C4 O1 119.3(3)
C4 C5 C6 118.9(3)
C4 C5 H5A 120.5
C6 C5 H5A 120.5
C5 C6 C7 119.7(3)
C5 C6 H6A 120.2
C7 C6 H6A 120.2
C2 C7 C6 121.7(3)
C2 C7 H7A 119.2
C6 C7 H7A 119.2
C9 C8 O1 121.0(2)
C9 C8 C13 121.0(2)
O1 C8 C13 118.0(2)
C8 C9 C10 119.8(2)
C8 C9 H9A 120.1
C10 C9 H9A 120.1
C11 C10 C9 120.7(2)
C11 C10 H10A 119.7
C9 C10 H10A 119.7
C10 C11 C12 119.9(2)
C10 C11 H11A 120.1
C12 C11 H11A 120.1
C11 C12 C13 121.4(2)
C11 C12 H12A 119.3
C13 C12 H12A 119.3
C8 C13 C12 117.2(2)
C8 C13 C14 123.17(19)
C12 C13 C14 119.6(2)
O2 C14 O3 121.7(2)
O2 C14 C13 124.1(2)
O3 C14 C13 114.12(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.380(2)
O1 C4 1.389(3)
C1 C2 1.506(4)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
O2 C14 1.222(2)
C2 C7 1.365(4)
C2 C3 1.380(3)
O3 C14 1.304(2)
O3 H3B 0.8200
C3 C4 1.380(3)
C3 H3A 0.9300
C4 C5 1.355(4)
C5 C6 1.371(3)
C5 H5A 0.9300
C6 C7 1.384(4)
C6 H6A 0.9300
C7 H7A 0.9300
C8 C9 1.377(3)
C8 C13 1.390(3)
C9 C10 1.378(3)
C9 H9A 0.9300
C10 C11 1.357(3)
C10 H10A 0.9300
C11 C12 1.371(3)
C11 H11A 0.9300
C12 C13 1.401(3)
C12 H12A 0.9300
C13 C14 1.476(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
O3 H3B O2 2_777 0.82 1.83 2.648(2) 176 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
C7 C2 C3 C4 -0.9(4)
C1 C2 C3 C4 179.0(2)
C2 C3 C4 C5 0.0(4)
C2 C3 C4 O1 175.7(2)
C8 O1 C4 C5 -110.5(3)
C8 O1 C4 C3 73.7(3)
C3 C4 C5 C6 1.3(4)
O1 C4 C5 C6 -174.5(2)
C4 C5 C6 C7 -1.6(4)
C3 C2 C7 C6 0.6(4)
C1 C2 C7 C6 -179.3(3)
C5 C6 C7 C2 0.7(4)
C4 O1 C8 C9 18.2(4)
C4 O1 C8 C13 -164.2(2)
O1 C8 C9 C10 178.4(2)
C13 C8 C9 C10 0.9(4)
C8 C9 C10 C11 -0.2(4)
C9 C10 C11 C12 -0.4(4)
C10 C11 C12 C13 0.4(4)
C9 C8 C13 C12 -0.9(3)
O1 C8 C13 C12 -178.5(2)
C9 C8 C13 C14 178.8(2)
O1 C8 C13 C14 1.2(3)
C11 C12 C13 C8 0.2(4)
C11 C12 C13 C14 -179.4(2)
C8 C13 C14 O2 -0.6(4)
C12 C13 C14 O2 179.0(2)
C8 C13 C14 O3 178.6(2)
C12 C13 C14 O3 -1.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 205777
