#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/85/2018584.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_2018584
loop_
_publ_author_name
'Santos, L. M.'
'Legendre, A. O.'
'Villis, P. C. M.'
'Viegas Jr, C.'
'Doriguetto, A. C.'
_publ_section_title
;
 (+-)-2,2-Dimethyl-5-oxotetrahydrofuran-3-carboxylic acid (terebic acid):
 a racemic layered structure
;
_journal_coeditor_code           UK3046
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o294
_journal_page_last               o297
_journal_paper_doi               10.1107/S0108270112029563
_journal_volume                  68
_journal_year                    2012
_chemical_formula_analytical     'C7 H10 O4'
_chemical_formula_iupac          'C7 H10 O4'
_chemical_formula_moiety         'C7 H10 O4'
_chemical_formula_sum            'C7 H10 O4'
_chemical_formula_weight         158.15
_chemical_name_common            'terebic acid'
_chemical_name_systematic
;
(+-)-2,2-Dimethyl-5-oxotetrahydrofuran-3-carboxylic 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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9890(10)
_cell_length_b                   5.6630(10)
_cell_length_c                   22.2820(10)
_cell_measurement_reflns_used    2814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.682
_cell_measurement_theta_min      2.91
_cell_volume                     749.96(19)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2864
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.0594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                1130
_reflns_number_total             1516
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            uk3046.cif
_cod_data_source_block           I
_cod_original_cell_volume        750.0(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018584
_cod_database_fobs_code          2018584
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
C C1 0.1384(2) 0.7159(2) 0.09276(6) 0.0421(4) Uani d . 1
H H1 0.0216 0.8344 0.0813 0.051 Uiso calc R 1
C C2 0.3341(2) 0.7630(3) 0.05786(6) 0.0497(4) Uani d . 1
H H2A 0.4144 0.6183 0.0514 0.06 Uiso calc R 1
H H2B 0.2838 0.8347 0.019 0.06 Uiso calc R 1
C C3 0.4780(2) 0.9284(3) 0.09742(7) 0.0461(4) Uani d . 1
C C4 0.2389(2) 0.7599(2) 0.15913(6) 0.0435(4) Uani d . 1
C C5 0.0359(2) 0.4746(3) 0.08306(7) 0.0459(4) Uani d . 1
C C6 0.0779(3) 0.8764(3) 0.19646(7) 0.0587(5) Uani d . 1
H H6A 0.0288 1.0241 0.1782 0.088 Uiso calc R 1
H H6B 0.1519 0.9041 0.2366 0.088 Uiso calc R 1
H H6C -0.0498 0.7755 0.1984 0.088 Uiso calc R 1
C C7 0.3506(3) 0.5455(3) 0.19020(7) 0.0566(4) Uani d . 1
H H7A 0.4523 0.477 0.165 0.085 Uiso calc R 1
H H7B 0.2379 0.4317 0.1972 0.085 Uiso calc R 1
H H7C 0.4325 0.5918 0.2281 0.085 Uiso calc R 1
O O1 0.63122(18) 1.0478(2) 0.08425(5) 0.0612(4) Uani d . 1
O O2 -0.15315(18) 0.4562(2) 0.10829(6) 0.0639(4) Uani d . 1
H H2 -0.219(3) 0.308(4) 0.0998(9) 0.096 Uiso d . 1
O O3 0.41873(16) 0.93195(19) 0.15283(4) 0.0507(3) Uani d . 1
O O4 0.11153(18) 0.3154(2) 0.05664(5) 0.0626(4) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C5 C1 C2 114.61(12)
C5 C1 C4 112.84(11)
C2 C1 C4 103.22(11)
C5 C1 H1 108.6
C2 C1 H1 108.6
C4 C1 H1 108.6
C3 C2 C1 103.68(12)
C3 C2 H2A 111
C1 C2 H2A 111
C3 C2 H2B 111
C1 C2 H2B 111
H2A C2 H2B 109
O1 C3 O3 121.16(13)
O1 C3 C2 127.77(13)
O3 C3 C2 111.07(12)
O3 C4 C6 106.80(12)
O3 C4 C7 106.71(11)
C6 C4 C7 112.17(13)
O3 C4 C1 102.64(10)
C6 C4 C1 113.54(12)
C7 C4 C1 114.00(12)
O4 C5 O2 122.91(14)
O4 C5 C1 125.68(14)
O2 C5 C1 111.40(13)
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 O2 H2 110.1(12)
C3 O3 C4 111.19(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.503(2)
C1 C2 1.5080(19)
C1 C4 1.5468(19)
C1 H1 0.98
C2 C3 1.487(2)
C2 H2A 0.97
C2 H2B 0.97
C3 O1 1.2049(17)
C3 O3 1.3262(17)
C4 O3 1.4718(16)
C4 C6 1.501(2)
C4 C7 1.512(2)
C5 O4 1.1958(18)
C5 O2 1.3285(18)
C6 H6A 0.96
C6 H6B 0.96
C6 H6C 0.96
C7 H7A 0.96
C7 H7B 0.96
C7 H7C 0.96
O2 H2 0.94(2)
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
C2 H2A O4 . 0.97 2.51 2.863(2) 101.3 yes
O2 H2 O1 1_445 0.91(2) 1.77(2) 2.673(2) 174(2) yes
C2 H2B O1 3_675 0.97 2.51 3.373(2) 148.7 yes
C1 H1 O1 1_455 0.98 2.64 3.557(2) 155.9 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 91750
2 PubChem 736106
