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#$Date: 2022-03-23 11:32:58 +0200 (Wed, 23 Mar 2022) $
#$Revision: 273925 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104842.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8104842
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid,
 C15H14O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              393
_journal_page_last               395
_journal_paper_doi               10.1515/ncrs-2020-0576
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C15 H14 O4'
_chemical_formula_sum            'C15 H14 O4'
_chemical_formula_weight         258.26
_chemical_name_common
;
α-(meta-methoxyphenoxyl)-ortho-tolylic acid
;
_chemical_name_systematic
;
α-(meta-methoxyphenoxyl)-ortho-tolylic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.7070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.1122(8)
_cell_length_b                   6.4295(2)
_cell_length_c                   14.7495(4)
_cell_measurement_reflns_used    6944
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.76
_cell_volume                     2569.96(13)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11956
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         2.763
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9321
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS[6]
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0518P)²+1.5140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2710
_reflns_number_total             3185
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0576_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8104842
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_iucr_geom_bonds_special_details
;                                                              
Cg(1) is the centroid of carbon atoms C21..C26.   

Cg(1) is the centroid of carbon atoms C11..C16.             
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20646(3) -0.38416(14) 0.57101(6) 0.0395(2) Uani 1 1 d . . . . .
H1 H 0.234382 -0.388608 0.551217 0.059 Uiso 1 1 d R U . . .
O2 O 0.20664(3) -0.07355(13) 0.50352(6) 0.0378(2) Uani 1 1 d . . . . .
O3 O 0.08376(3) 0.29500(13) 0.46669(6) 0.0353(2) Uani 1 1 d . . . . .
O4 O 0.19783(3) 0.68803(15) 0.29798(6) 0.0449(2) Uani 1 1 d . . . . .
C1 C 0.18548(4) -0.20648(17) 0.54735(7) 0.0285(2) Uani 1 1 d . . . . .
C2 C 0.12336(4) 0.15614(17) 0.49000(7) 0.0287(2) Uani 1 1 d . . . . .
H2A H 0.150146 0.232738 0.522571 0.034 Uiso 1 1 calc R U . . .
H2B H 0.136890 0.095431 0.434285 0.034 Uiso 1 1 calc R U . . .
C3 C 0.20937(6) 0.8607(3) 0.24244(12) 0.0591(4) Uani 1 1 d . . . . .
H3A H 0.198991 0.989451 0.271922 0.089 Uiso 1 1 calc R U . . .
H3B H 0.192034 0.846998 0.183489 0.089 Uiso 1 1 calc R U . . .
H3C H 0.245034 0.864906 0.233599 0.089 Uiso 1 1 calc R U . . .
C11 C 0.13397(4) -0.18336(17) 0.57777(7) 0.0273(2) Uani 1 1 d . . . . .
C12 C 0.10408(4) -0.01430(16) 0.54958(7) 0.0268(2) Uani 1 1 d . . . . .
C13 C 0.05531(4) -0.00951(18) 0.57781(8) 0.0320(2) Uani 1 1 d . . . . .
H13 H 0.034508 0.102647 0.559433 0.038 Uiso 1 1 calc R U . . .
C14 C 0.03673(4) -0.1654(2) 0.63214(9) 0.0378(3) Uani 1 1 d . . . . .
H14 H 0.003282 -0.160242 0.649467 0.045 Uiso 1 1 calc R U . . .
C15 C 0.06650(5) -0.3283(2) 0.66127(9) 0.0393(3) Uani 1 1 d . . . . .
H15 H 0.053924 -0.432958 0.699727 0.047 Uiso 1 1 calc R U . . .
C16 C 0.11495(4) -0.33715(18) 0.63374(8) 0.0339(3) Uani 1 1 d . . . . .
H16 H 0.135462 -0.449344 0.653214 0.041 Uiso 1 1 calc R U . . .
C21 C 0.09531(4) 0.45783(17) 0.41143(7) 0.0297(2) Uani 1 1 d . . . . .
C22 C 0.14201(4) 0.49436(17) 0.37922(7) 0.0307(2) Uani 1 1 d . . . . .
H22 H 0.168483 0.403126 0.394865 0.037 Uiso 1 1 calc R U . . .
C23 C 0.14990(4) 0.66640(18) 0.32354(7) 0.0323(2) Uani 1 1 d . . . . .
C24 C 0.11140(5) 0.79812(18) 0.29836(8) 0.0366(3) Uani 1 1 d . . . . .
H24 H 0.116592 0.912808 0.259172 0.044 Uiso 1 1 calc R U . . .
C25 C 0.06482(5) 0.75787(19) 0.33206(8) 0.0382(3) Uani 1 1 d . . . . .
H25 H 0.038251 0.847979 0.315656 0.046 Uiso 1 1 calc R U . . .
C26 C 0.05608(4) 0.59172(18) 0.38835(8) 0.0344(3) Uani 1 1 d . . . . .
H26 H 0.024130 0.568332 0.411063 0.041 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 H1 109.4 . .
C21 O3 C2 115.93(8) . .
C23 O4 C3 117.69(11) . .
O2 C1 O1 122.63(10) . .
O2 C1 C11 123.27(10) . .
O1 C1 C11 114.10(9) . .
O3 C2 C12 108.85(8) . .
O3 C2 H2A 109.9 . .
C12 C2 H2A 109.9 . .
O3 C2 H2B 109.9 . .
C12 C2 H2B 109.9 . .
H2A C2 H2B 108.3 . .
O4 C3 H3A 109.5 . .
O4 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
O4 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C16 C11 C12 120.05(10) . .
C16 C11 C1 118.31(10) . .
C12 C11 C1 121.62(10) . .
C13 C12 C11 117.97(10) . .
C13 C12 C2 120.31(10) . .
C11 C12 C2 121.71(9) . .
C14 C13 C12 121.26(11) . .
C14 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C15 C14 C13 120.52(11) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C16 119.28(11) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C15 C16 C11 120.88(11) . .
C15 C16 H16 119.6 . .
C11 C16 H16 119.6 . .
O3 C21 C22 124.14(10) . .
O3 C21 C26 115.40(10) . .
C22 C21 C26 120.46(10) . .
C21 C22 C23 119.53(10) . .
C21 C22 H22 120.2 . .
C23 C22 H22 120.2 . .
O4 C23 C24 125.23(11) . .
O4 C23 C22 113.87(10) . .
C24 C23 C22 120.90(11) . .
C23 C24 C25 118.28(11) . .
C23 C24 H24 120.9 . .
C25 C24 H24 120.9 . .
C26 C25 C24 122.15(11) . .
C26 C25 H25 118.9 . .
C24 C25 H25 118.9 . .
C25 C26 C21 118.65(11) . .
C25 C26 H26 120.7 . .
C21 C26 H26 120.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3186(13) .
O1 H1 0.8199 .
O2 C1 1.2246(13) .
O3 C21 1.3687(13) .
O3 C2 1.4303(12) .
O4 C23 1.3708(14) .
O4 C3 1.4202(16) .
C1 C11 1.4870(14) .
C2 C12 1.5079(15) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C11 C16 1.3965(15) .
C11 C12 1.4111(15) .
C12 C13 1.3983(15) .
C13 C14 1.3875(17) .
C13 H13 0.9500 .
C14 C15 1.3827(18) .
C14 H14 0.9500 .
C15 C16 1.3877(17) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.3857(16) .
C21 C26 1.4023(15) .
C22 C23 1.3980(16) .
C22 H22 0.9500 .
C23 C24 1.3864(17) .
C24 C25 1.3951(19) .
C24 H24 0.9500 .
C25 C26 1.3778(17) .
C25 H25 0.9500 .
C26 H26 0.9500 .
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
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.83 2.6433(11) 172.1 7_546
C15 H15 <i>C<i>~g~(1) 0.95 2.91 3.5686(14) 128 4_555
C24 H24 <i>C<i>~g~(2) 0.95 2.92 3.7806(13) 151 4_564
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C21 O3 C2 C12 -179.19(8) . . . .
O2 C1 C11 C16 -174.79(11) . . . .
O1 C1 C11 C16 5.78(14) . . . .
O2 C1 C11 C12 6.87(16) . . . .
O1 C1 C11 C12 -172.56(10) . . . .
C16 C11 C12 C13 -1.32(16) . . . .
C1 C11 C12 C13 177.00(10) . . . .
C16 C11 C12 C2 179.34(10) . . . .
C1 C11 C12 C2 -2.35(15) . . . .
O3 C2 C12 C13 -4.17(14) . . . .
O3 C2 C12 C11 175.15(9) . . . .
C11 C12 C13 C14 0.22(17) . . . .
C2 C12 C13 C14 179.57(10) . . . .
C12 C13 C14 C15 1.25(19) . . . .
C13 C14 C15 C16 -1.6(2) . . . .
C14 C15 C16 C11 0.48(19) . . . .
C12 C11 C16 C15 0.99(17) . . . .
C1 C11 C16 C15 -177.38(11) . . . .
C2 O3 C21 C22 -0.84(15) . . . .
C2 O3 C21 C26 179.41(10) . . . .
O3 C21 C22 C23 -179.58(10) . . . .
C26 C21 C22 C23 0.17(16) . . . .
C3 O4 C23 C24 1.06(19) . . . .
C3 O4 C23 C22 -179.04(12) . . . .
C21 C22 C23 O4 178.54(10) . . . .
C21 C22 C23 C24 -1.55(17) . . . .
O4 C23 C24 C25 -178.36(11) . . . .
C22 C23 C24 C25 1.74(17) . . . .
C23 C24 C25 C26 -0.58(18) . . . .
C24 C25 C26 C21 -0.76(18) . . . .
O3 C21 C26 C25 -179.27(10) . . . .
C22 C21 C26 C25 0.96(17) . . . .
