#------------------------------------------------------------------------------
#$Date: 2023-02-13 11:42:27 +0200 (Mon, 13 Feb 2023) $
#$Revision: 280873 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106769.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_8106769
loop_
_publ_author_name
'Yuan, Xian-You'
'Jia, Guo-Kai'
'Zhang, Min'
'Yuan, Lin'
_publ_section_title
;
 Crystal structure of 5-methyl-2-phenyl-1,3-dioxane-5-carboxylic acid,
 C12H14O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              5
_journal_page_last               7
_journal_paper_doi               10.1515/ncrs-2014-9009
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.368(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   32.6674(8)
_cell_length_b                   6.0061(2)
_cell_length_c                   23.2786(6)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.56
_cell_volume                     4443.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17586
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0459
_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)+(0.1051P)²+1.2579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1711
_reflns_number_gt                4119
_reflns_number_total             5049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2014-9009_suppl.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106769
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18934(3) 0.39122(17) 0.24551(4) 0.0387(3) Uani 1 1 d . . .
O2 O 0.27339(3) 0.3853(2) 0.34901(5) 0.0487(3) Uani 1 1 d D . .
H2 H 0.2916(6) 0.473(3) 0.3740(8) 0.073 Uiso 1 1 d D . .
O3 O 0.23661(3) 0.3879(2) 0.41775(5) 0.0499(3) Uani 1 1 d . . .
O4 O 0.14921(3) 0.38665(17) 0.31569(4) 0.0387(3) Uani 1 1 d . . .
O5 O 0.38551(3) 0.61187(17) 0.58090(4) 0.0402(3) Uani 1 1 d . . .
O6 O 0.29423(4) 0.6389(2) 0.48855(5) 0.0519(3) Uani 1 1 d D . .
H16 H 0.2744(6) 0.559(4) 0.4621(8) 0.078 Uiso 1 1 d D . .
O7 O 0.32670(3) 0.6565(2) 0.41481(5) 0.0510(3) Uani 1 1 d . . .
O8 O 0.41766(3) 0.64225(17) 0.50202(4) 0.0402(3) Uani 1 1 d . . .
C1 C 0.07647(6) 0.9375(3) 0.16692(9) 0.0682(6) Uani 1 1 d . . .
H1 H 0.0603 1.0532 0.1470 0.082 Uiso 1 1 calc R . .
C2 C 0.10546(6) 0.8336(4) 0.14244(9) 0.0701(6) Uani 1 1 d . . .
H12 H 0.1091 0.8789 0.1057 0.084 Uiso 1 1 calc R . .
C3 C 0.12947(6) 0.6615(3) 0.17187(8) 0.0565(4) Uani 1 1 d . . .
H11 H 0.1492 0.5924 0.1548 0.068 Uiso 1 1 calc R . .
C4 C 0.12460(4) 0.5904(2) 0.22634(6) 0.0400(3) Uani 1 1 d . . .
C5 C 0.14822(4) 0.3897(2) 0.25489(6) 0.0362(3) Uani 1 1 d . . .
H10 H 0.1337 0.2556 0.2367 0.043 Uiso 1 1 calc R . .
C6 C 0.21027(5) 0.1876(2) 0.26667(6) 0.0397(3) Uani 1 1 d . . .
H9 H 0.2386 0.1893 0.2602 0.048 Uiso 1 1 calc R . .
H8 H 0.1953 0.0633 0.2448 0.048 Uiso 1 1 calc R . .
C7 C 0.21231(4) 0.1572(2) 0.33236(5) 0.0344(3) Uani 1 1 d . . .
C8 C 0.24208(4) 0.3246(2) 0.36905(5) 0.0322(3) Uani 1 1 d . . .
C9 C 0.07134(6) 0.8705(3) 0.22111(9) 0.0665(5) Uani 1 1 d . . .
H14 H 0.0517 0.9414 0.2379 0.080 Uiso 1 1 calc R . .
C10 C 0.09534(5) 0.6975(3) 0.25106(7) 0.0535(4) Uani 1 1 d . . .
H13 H 0.0917 0.6536 0.2879 0.064 Uiso 1 1 calc R . .
C11 C 0.16801(4) 0.1847(2) 0.34186(6) 0.0389(3) Uani 1 1 d . . .
H4 H 0.1509 0.0591 0.3246 0.047 Uiso 1 1 calc R . .
H3 H 0.1691 0.1864 0.3839 0.047 Uiso 1 1 calc R . .
C12 C 0.22935(6) -0.0753(3) 0.35250(8) 0.0529(4) Uani 1 1 d . . .
H6 H 0.2573 -0.0909 0.3465 0.079 Uiso 1 1 calc R . .
H7 H 0.2114 -0.1865 0.3300 0.079 Uiso 1 1 calc R . .
H5 H 0.2300 -0.0940 0.3937 0.079 Uiso 1 1 calc R . .
C13 C 0.50190(6) 0.0598(3) 0.62881(10) 0.0695(6) Uani 1 1 d . . .
H15 H 0.5200 -0.0561 0.6442 0.083 Uiso 1 1 calc R . .
C14 C 0.47540(7) 0.1471(4) 0.66086(9) 0.0721(6) Uani 1 1 d . . .
H17 H 0.4751 0.0870 0.6976 0.087 Uiso 1 1 calc R . .
C15 C 0.44907(6) 0.3241(3) 0.63907(7) 0.0587(5) Uani 1 1 d . . .
H18 H 0.4312 0.3818 0.6611 0.070 Uiso 1 1 calc R . .
C16 C 0.44948(4) 0.4149(3) 0.58440(6) 0.0417(3) Uani 1 1 d . . .
C17 C 0.42429(4) 0.6204(2) 0.56379(6) 0.0383(3) Uani 1 1 d . . .
H26 H 0.4401 0.7503 0.5825 0.046 Uiso 1 1 calc R . .
C18 C 0.36336(5) 0.8184(2) 0.56731(6) 0.0407(3) Uani 1 1 d . . .
H19 H 0.3797 0.9379 0.5895 0.049 Uiso 1 1 calc R . .
H25 H 0.3367 0.8101 0.5788 0.049 Uiso 1 1 calc R . .
C19 C 0.35547(4) 0.8682(2) 0.50144(6) 0.0357(3) Uani 1 1 d . . .
C20 C 0.32389(4) 0.7070(2) 0.46566(6) 0.0329(3) Uani 1 1 d . . .
C21 C 0.50156(5) 0.1443(3) 0.57399(10) 0.0628(5) Uani 1 1 d . . .
H28 H 0.5189 0.0827 0.5517 0.075 Uiso 1 1 calc R . .
C22 C 0.47550(5) 0.3209(3) 0.55177(8) 0.0503(4) Uani 1 1 d . . .
H27 H 0.4755 0.3770 0.5145 0.060 Uiso 1 1 calc R . .
C23 C 0.33733(6) 1.1036(2) 0.48868(8) 0.0502(4) Uani 1 1 d . . .
H22 H 0.3325 1.1335 0.4471 0.075 Uiso 1 1 calc R . .
H21 H 0.3569 1.2104 0.5101 0.075 Uiso 1 1 calc R . .
H20 H 0.3112 1.1143 0.5008 0.075 Uiso 1 1 calc R . .
C24 C 0.39745(4) 0.8494(2) 0.48327(7) 0.0407(3) Uani 1 1 d . . .
H24 H 0.3926 0.8616 0.4407 0.049 Uiso 1 1 calc R . .
H23 H 0.4157 0.9710 0.5007 0.049 Uiso 1 1 calc R . .
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
C5 O1 C6 109.73(10) . .
C8 O2 H2 113.3(14) . .
C5 O4 C11 110.30(10) . .
C17 O5 C18 110.23(10) . .
C20 O6 H16 111.8(14) . .
C17 O8 C24 110.10(10) . .
C2 C1 C9 119.62(17) . .
C2 C1 H1 120.2 . .
C9 C1 H1 120.2 . .
C1 C2 C3 120.34(18) . .
C1 C2 H12 119.8 . .
C3 C2 H12 119.8 . .
C2 C3 C4 120.95(18) . .
C2 C3 H11 119.5 . .
C4 C3 H11 119.5 . .
C3 C4 C10 118.38(15) . .
C3 C4 C5 119.88(14) . .
C10 C4 C5 121.56(14) . .
O4 C5 O1 110.75(10) . .
O4 C5 C4 110.21(11) . .
O1 C5 C4 109.70(11) . .
O4 C5 H10 108.7 . .
O1 C5 H10 108.7 . .
C4 C5 H10 108.7 . .
O1 C6 C7 110.72(10) . .
O1 C6 H9 109.5 . .
C7 C6 H9 109.5 . .
O1 C6 H8 109.5 . .
C7 C6 H8 109.5 . .
H9 C6 H8 108.1 . .
C8 C7 C11 110.68(11) . .
C8 C7 C6 111.00(11) . .
C11 C7 C6 108.04(11) . .
C8 C7 C12 106.92(11) . .
C11 C7 C12 110.11(12) . .
C6 C7 C12 110.10(12) . .
O3 C8 O2 122.86(12) . .
O3 C8 C7 120.38(11) . .
O2 C8 C7 116.66(11) . .
C1 C9 C10 120.47(19) . .
C1 C9 H14 119.8 . .
C10 C9 H14 119.8 . .
C4 C10 C9 120.23(17) . .
C4 C10 H13 119.9 . .
C9 C10 H13 119.9 . .
O4 C11 C7 111.06(10) . .
O4 C11 H4 109.4 . .
C7 C11 H4 109.4 . .
O4 C11 H3 109.4 . .
C7 C11 H3 109.4 . .
H4 C11 H3 108.0 . .
C7 C12 H6 109.5 . .
C7 C12 H7 109.5 . .
H6 C12 H7 109.5 . .
C7 C12 H5 109.5 . .
H6 C12 H5 109.5 . .
H7 C12 H5 109.5 . .
C21 C13 C14 119.66(18) . .
C21 C13 H15 120.2 . .
C14 C13 H15 120.2 . .
C13 C14 C15 120.66(19) . .
C13 C14 H17 119.7 . .
C15 C14 H17 119.7 . .
C14 C15 C16 120.00(18) . .
C14 C15 H18 120.0 . .
C16 C15 H18 120.0 . .
C22 C16 C15 118.69(16) . .
C22 C16 C17 121.42(14) . .
C15 C16 C17 119.75(14) . .
O8 C17 O5 110.75(10) . .
O8 C17 C16 110.26(11) . .
O5 C17 C16 109.95(11) . .
O8 C17 H26 108.6 . .
O5 C17 H26 108.6 . .
C16 C17 H26 108.6 . .
O5 C18 C19 110.55(11) . .
O5 C18 H19 109.5 . .
C19 C18 H19 109.5 . .
O5 C18 H25 109.5 . .
C19 C18 H25 109.5 . .
H19 C18 H25 108.1 . .
C20 C19 C18 111.25(11) . .
C20 C19 C24 109.91(11) . .
C18 C19 C24 108.04(11) . .
C20 C19 C23 107.38(11) . .
C18 C19 C23 110.09(12) . .
C24 C19 C23 110.18(12) . .
O7 C20 O6 123.26(12) . .
O7 C20 C19 119.18(11) . .
O6 C20 C19 117.46(11) . .
C13 C21 C22 120.26(18) . .
C13 C21 H28 119.9 . .
C22 C21 H28 119.9 . .
C21 C22 C16 120.68(17) . .
C21 C22 H27 119.7 . .
C16 C22 H27 119.7 . .
C19 C23 H22 109.5 . .
C19 C23 H21 109.5 . .
H22 C23 H21 109.5 . .
C19 C23 H20 109.5 . .
H22 C23 H20 109.5 . .
H21 C23 H20 109.5 . .
O8 C24 C19 111.11(11) . .
O8 C24 H24 109.4 . .
C19 C24 H24 109.4 . .
O8 C24 H23 109.4 . .
C19 C24 H23 109.4 . .
H24 C24 H23 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.4100(16) .
O1 C6 1.4319(17) .
O2 C8 1.2716(16) .
O2 H2 0.901(15) .
O3 C8 1.2473(16) .
O4 C5 1.4083(15) .
O4 C11 1.4306(17) .
O5 C17 1.4139(16) .
O5 C18 1.4339(17) .
O6 C20 1.2762(17) .
O6 H16 0.920(15) .
O7 C20 1.2457(16) .
O8 C17 1.4100(16) .
O8 C24 1.4287(17) .
C1 C2 1.364(3) .
C1 C9 1.371(3) .
C1 H1 0.9300 .
C2 C3 1.380(3) .
C2 H12 0.9300 .
C3 C4 1.382(2) .
C3 H11 0.9300 .
C4 C10 1.383(2) .
C4 C5 1.5008(19) .
C5 H10 0.9800 .
C6 C7 1.5260(18) .
C6 H9 0.9700 .
C6 H8 0.9700 .
C7 C8 1.5175(17) .
C7 C11 1.5227(18) .
C7 C12 1.5357(19) .
C9 C10 1.388(2) .
C9 H14 0.9300 .
C10 H13 0.9300 .
C11 H4 0.9700 .
C11 H3 0.9700 .
C12 H6 0.9600 .
C12 H7 0.9600 .
C12 H5 0.9600 .
C13 C21 1.371(3) .
C13 C14 1.371(3) .
C13 H15 0.9300 .
C14 C15 1.387(3) .
C14 H17 0.9300 .
C15 C16 1.388(2) .
C15 H18 0.9300 .
C16 C22 1.385(2) .
C16 C17 1.499(2) .
C17 H26 0.9800 .
C18 C19 1.5246(19) .
C18 H19 0.9700 .
C18 H25 0.9700 .
C19 C20 1.5161(17) .
C19 C24 1.5301(19) .
C19 C23 1.5354(19) .
C21 C22 1.383(2) .
C21 H28 0.9300 .
C22 H27 0.9300 .
C23 H22 0.9600 .
C23 H21 0.9600 .
C23 H20 0.9600 .
C24 H24 0.9700 .
C24 H23 0.9700 .
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
C9 C1 C2 C3 0.2(3) . . . .
C1 C2 C3 C4 0.3(3) . . . .
C2 C3 C4 C10 -0.7(3) . . . .
C2 C3 C4 C5 174.42(16) . . . .
C11 O4 C5 O1 -64.16(13) . . . .
C11 O4 C5 C4 174.27(10) . . . .
C6 O1 C5 O4 64.81(13) . . . .
C6 O1 C5 C4 -173.32(10) . . . .
C3 C4 C5 O4 161.91(13) . . . .
C10 C4 C5 O4 -23.13(18) . . . .
C3 C4 C5 O1 39.71(17) . . . .
C10 C4 C5 O1 -145.32(14) . . . .
C5 O1 C6 C7 -59.05(13) . . . .
O1 C6 C7 C8 -69.46(14) . . . .
O1 C6 C7 C11 52.06(14) . . . .
O1 C6 C7 C12 172.35(11) . . . .
C11 C7 C8 O3 32.00(17) . . . .
C6 C7 C8 O3 151.96(13) . . . .
C12 C7 C8 O3 -87.94(15) . . . .
C11 C7 C8 O2 -151.62(12) . . . .
C6 C7 C8 O2 -31.65(16) . . . .
C12 C7 C8 O2 88.45(15) . . . .
C2 C1 C9 C10 -0.2(3) . . . .
C3 C4 C10 C9 0.7(3) . . . .
C5 C4 C10 C9 -174.35(14) . . . .
C1 C9 C10 C4 -0.3(3) . . . .
C5 O4 C11 C7 57.72(13) . . . .
C8 C7 C11 O4 70.40(13) . . . .
C6 C7 C11 O4 -51.32(14) . . . .
C12 C7 C11 O4 -171.60(11) . . . .
C21 C13 C14 C15 -1.8(3) . . . .
C13 C14 C15 C16 -0.2(3) . . . .
C14 C15 C16 C22 2.0(3) . . . .
C14 C15 C16 C17 -173.76(15) . . . .
C24 O8 C17 O5 64.01(13) . . . .
C24 O8 C17 C16 -174.07(10) . . . .
C18 O5 C17 O8 -64.44(13) . . . .
C18 O5 C17 C16 173.45(10) . . . .
C22 C16 C17 O8 23.67(17) . . . .
C15 C16 C17 O8 -160.63(13) . . . .
C22 C16 C17 O5 146.06(13) . . . .
C15 C16 C17 O5 -38.24(17) . . . .
C17 O5 C18 C19 58.61(13) . . . .
O5 C18 C19 C20 68.92(14) . . . .
O5 C18 C19 C24 -51.80(14) . . . .
O5 C18 C19 C23 -172.17(11) . . . .
C18 C19 C20 O7 -149.15(13) . . . .
C24 C19 C20 O7 -29.53(17) . . . .
C23 C19 C20 O7 90.33(15) . . . .
C18 C19 C20 O6 34.44(17) . . . .
C24 C19 C20 O6 154.06(13) . . . .
C23 C19 C20 O6 -86.08(15) . . . .
C14 C13 C21 C22 1.9(3) . . . .
C13 C21 C22 C16 0.1(3) . . . .
C15 C16 C22 C21 -2.0(2) . . . .
C17 C16 C22 C21 173.74(14) . . . .
C17 O8 C24 C19 -58.11(13) . . . .
C20 C19 C24 O8 -69.76(14) . . . .
C18 C19 C24 O8 51.80(14) . . . .
C23 C19 C24 O8 172.11(12) . . . .
