#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208231.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_2208231
loop_
_publ_author_name
'Samas, Brian'
'Pflum, Derek A.'
'Coscia, Rockford W.'
_publ_section_title
;
 (E,E)-1,8-Dioxacyclotetradeca-3,10-diene-2,9-dione
;
_journal_coeditor_code           AC6231
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1121
_journal_page_last               o1122
_journal_paper_doi               10.1107/S1600536806005745
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H16 O4'
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25
_chemical_name_systematic
;
(E,E)-1,8-Dioxacyclotetradeca-3,10-diene-2,9-dione
;
_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
_cell_angle_alpha                72.037(7)
_cell_angle_beta                 77.661(8)
_cell_angle_gamma                68.409(7)
_cell_formula_units_Z            1
_cell_length_a                   6.442(3)
_cell_length_b                   6.665(3)
_cell_length_c                   7.757(4)
_cell_measurement_reflns_used    938
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0.93
_cell_measurement_theta_min      28.28
_cell_volume                     292.7(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5226
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.7537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.161
_refine_ls_extinction_coef       0.17(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0419
_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)+(0.0712P)²+0.031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                1278
_reflns_number_total             1440
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6231.cif
_cod_data_source_block           4
_cod_database_code               2208231
_cod_database_fobs_code          2208231
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
O O2 0.33098(13) 0.81151(13) -0.11673(10) 0.0483(3) Uani d . 1
C C1 0.59655(19) 0.72251(16) 0.07816(15) 0.0446(3) Uani d . 1
C C2 0.55029(19) 0.77086(17) -0.11113(15) 0.0454(3) Uani d . 1
C C3 0.7891(2) 0.71892(17) 0.11454(15) 0.0465(3) Uani d . 1
O O1 0.68569(16) 0.7824(2) -0.24410(12) 0.0713(3) Uani d . 1
C C4 0.8471(2) 0.69366(19) 0.29840(16) 0.0537(3) Uani d . 1
H H4A 0.9627 0.5508 0.3339 0.064 Uiso calc R 1
H H4B 0.7154 0.6932 0.3866 0.064 Uiso calc R 1
C C5 0.2471(2) 0.8963(2) -0.29373(16) 0.0558(3) Uani d . 1
H H5A 0.1837 0.7937 -0.3114 0.067 Uiso calc R 1
H H5B 0.3698 0.9086 -0.3893 0.067 Uiso calc R 1
C C6 0.9303(2) 0.8781(2) 0.30483(17) 0.0551(3) Uani d . 1
H H6A 0.9970 0.8329 0.4174 0.066 Uiso calc R 1
H H6B 1.0477 0.8923 0.2047 0.066 Uiso calc R 1
H H99A 0.473(2) 0.712(2) 0.167(2) 0.058(4) Uiso d . 1
H H99B 0.903(2) 0.736(2) 0.0155(19) 0.056(4) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0550(5) 0.0481(4) 0.0446(4) -0.0188(3) -0.0124(3) -0.0087(3)
C1 0.0498(6) 0.0361(5) 0.0437(5) -0.0097(4) -0.0075(5) -0.0080(4)
C2 0.0514(6) 0.0372(5) 0.0472(6) -0.0100(4) -0.0076(5) -0.0142(4)
C3 0.0499(6) 0.0390(5) 0.0454(6) -0.0070(4) -0.0080(5) -0.0108(4)
O1 0.0604(6) 0.1010(8) 0.0499(5) -0.0190(5) -0.0001(4) -0.0284(5)
C4 0.0597(7) 0.0478(6) 0.0483(6) -0.0105(5) -0.0186(5) -0.0051(5)
C5 0.0686(8) 0.0579(7) 0.0480(6) -0.0211(6) -0.0186(5) -0.0142(5)
C6 0.0546(7) 0.0628(7) 0.0495(6) -0.0173(5) -0.0195(5) -0.0094(5)
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
C2 O2 C5 . . 118.29(9)
C3 C1 C2 . . 121.28(11)
C3 C1 H99A . . 123.9(9)
C2 C1 H99A . . 114.5(9)
O1 C2 O2 . . 123.96(11)
O1 C2 C1 . . 125.48(12)
O2 C2 C1 . . 110.49(10)
C1 C3 C4 . . 126.20(11)
C1 C3 H99B . . 118.0(8)
C4 C3 H99B . . 115.8(8)
C3 C4 C6 . . 113.36(10)
C3 C4 H4A . . 108.9
C6 C4 H4A . . 108.9
C3 C4 H4B . . 108.9
C6 C4 H4B . . 108.9
H4A C4 H4B . . 107.7
O2 C5 C6 . 2_675 109.82(9)
O2 C5 H5A . . 109.7
C6 C5 H5A 2_675 . 109.7
O2 C5 H5B . . 109.7
C6 C5 H5B 2_675 . 109.7
H5A C5 H5B . . 108.2
C5 C6 C4 2_675 . 115.19(11)
C5 C6 H6A 2_675 . 108.5
C4 C6 H6A . . 108.5
C5 C6 H6B 2_675 . 108.5
C4 C6 H6B . . 108.5
H6A C6 H6B . . 107.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O2 C2 . 1.3449(15)
O2 C5 . 1.4528(14)
C1 C3 . 1.3201(18)
C1 C2 . 1.4742(16)
C1 H99A . 0.942(15)
C2 O1 . 1.2027(15)
C3 C4 . 1.4952(16)
C3 H99B . 0.953(15)
C4 C6 . 1.5281(19)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C6 2_675 1.5069(19)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 H6A . 0.9700
C6 H6B . 0.9700
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
C4 H4A O1 2_765 0.97 2.67 3.544(2) 150
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_4
_geom_torsion
C5 O2 C2 O1 . -6.53(16)
C5 O2 C2 C1 . 170.56(8)
C3 C1 C2 O1 . 9.95(18)
C3 C1 C2 O2 . -167.09(9)
C2 C1 C3 C4 . 173.80(9)
C1 C3 C4 C6 . -126.34(13)
C2 O2 C5 C6 2_675 -118.97(11)
C3 C4 C6 C5 2_675 71.46(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11746260
