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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504008.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_4504008
loop_
_publ_author_name
'Matsumoto, Akikazu'
'Furukawa, Daisuke'
'Mori, Yutaka'
'Tanaka, Toshihiro'
'Oka, Kunio'
_publ_section_title
;
 Change in Crystal Structure and Polymerization Reactivity for the
 Solid-State Polymerization of Muconic Esters
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1078
_journal_paper_doi               10.1021/cg0606444
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C22 H18 O8 '
_chemical_formula_sum            'C22 H18 O8'
_chemical_formula_weight         410.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.397(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.540(2)
_cell_length_b                   4.4318(7)
_cell_length_c                   18.858(4)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      4.3
_cell_volume                     942.0(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8628
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9568
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0429
_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)+(0.0478P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1241
_reflns_number_total             2156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0606444si20070319_011020.cif
_cod_data_source_block           MDO
_cod_original_cell_volume        941.9(3)
_cod_database_code               4504008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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
O1 O 0.90974(10) -0.0208(3) 0.35377(6) 0.0519(3) Uani 1 1 d .
O2 O 0.73768(10) -0.0714(2) 0.38994(6) 0.0441(3) Uani 1 1 d .
O3 O 0.71048(12) 0.0558(3) 0.08090(7) 0.0697(4) Uani 1 1 d .
O4 O 0.53138(12) 0.3040(3) 0.06472(7) 0.0697(4) Uani 1 1 d .
C1 C 0.84671(14) 0.0424(3) 0.39473(8) 0.0384(4) Uani 1 1 d .
C2 C 0.87914(15) 0.2527(4) 0.45624(8) 0.0409(4) Uani 1 1 d .
H2 H 0.8260 0.2842 0.4862 0.049 Uiso 1 1 calc R
C3 C 0.98140(15) 0.3981(4) 0.47012(8) 0.0411(4) Uani 1 1 d .
H3 H 1.0329 0.3663 0.4391 0.049 Uiso 1 1 calc R
C4 C 0.69454(15) -0.2800(4) 0.32990(9) 0.0469(4) Uani 1 1 d .
H4A H 0.6319 -0.4039 0.3416 0.056 Uiso 1 1 calc R
H4B H 0.7588 -0.4126 0.3241 0.056 Uiso 1 1 calc R
C5 C 0.64802(15) -0.1183(4) 0.25978(8) 0.0394(4) Uani 1 1 d .
C6 C 0.71252(15) -0.1193(4) 0.20513(9) 0.0459(4) Uani 1 1 d .
H6 H 0.7851 -0.2179 0.2113 0.055 Uiso 1 1 calc R
C7 C 0.66522(15) 0.0293(4) 0.14261(9) 0.0446(4) Uani 1 1 d .
C8 C 0.55887(15) 0.1777(4) 0.13274(9) 0.0461(4) Uani 1 1 d .
C9 C 0.49411(16) 0.1827(4) 0.18501(10) 0.0573(5) Uani 1 1 d .
H9 H 0.4219 0.2835 0.1782 0.069 Uiso 1 1 calc R
C10 C 0.54085(15) 0.0302(4) 0.24900(9) 0.0500(5) Uani 1 1 d .
H10 H 0.4985 0.0281 0.2858 0.060 Uiso 1 1 calc R
C11 C 0.63470(19) 0.2657(5) 0.03587(11) 0.0677(6) Uani 1 1 d .
H11A H 0.6750 0.4574 0.0352 0.081 Uiso 1 1 calc R
H11B H 0.6131 0.1900 -0.0135 0.081 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
C1 O2 C4 116.64(12) . .
C7 O3 C11 105.26(13) . .
C8 O4 C11 105.32(14) . .
O1 C1 O2 123.88(15) . .
O1 C1 C2 124.55(15) . .
O2 C1 C2 111.56(13) . .
C3 C2 C1 122.02(14) . .
C3 C2 H2 119.0 . .
C1 C2 H2 119.0 . .
C2 C3 C3 124.49(19) . 3_766
C2 C3 H3 117.8 . .
C3 C3 H3 117.8 3_766 .
O2 C4 C5 112.24(13) . .
O2 C4 H4A 109.2 . .
C5 C4 H4A 109.2 . .
O2 C4 H4B 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C10 C5 C6 119.83(15) . .
C10 C5 C4 119.93(14) . .
C6 C5 C4 120.24(15) . .
C7 C6 C5 117.45(15) . .
C7 C6 H6 121.3 . .
C5 C6 H6 121.3 . .
C6 C7 C8 122.16(15) . .
C6 C7 O3 128.26(15) . .
C8 C7 O3 109.58(15) . .
C9 C8 C7 121.70(16) . .
C9 C8 O4 128.20(17) . .
C7 C8 O4 110.08(14) . .
C8 C9 C10 116.84(16) . .
C8 C9 H9 121.6 . .
C10 C9 H9 121.6 . .
C5 C10 C9 122.03(15) . .
C5 C10 H10 119.0 . .
C9 C10 H10 119.0 . .
O4 C11 O3 107.89(14) . .
O4 C11 H11A 110.1 . .
O3 C11 H11A 110.1 . .
O4 C11 H11B 110.1 . .
O3 C11 H11B 110.1 . .
H11A C11 H11B 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2022(17) .
O2 C1 1.3405(19) .
O2 C4 1.4636(19) .
O3 C7 1.3790(19) .
O3 C11 1.426(2) .
O4 C8 1.373(2) .
O4 C11 1.423(2) .
C1 C2 1.472(2) .
C2 C3 1.320(2) .
C2 H2 0.9300 .
C3 C3 1.436(3) 3_766
C3 H3 0.9300 .
C4 C5 1.499(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C10 1.377(2) .
C5 C6 1.395(2) .
C6 C7 1.358(2) .
C6 H6 0.9300 .
C7 C8 1.370(2) .
C8 C9 1.359(2) .
C9 C10 1.387(2) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 H11A 0.9700 .
C11 H11B 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_4
C4 O2 C1 O1 -1.2(2) .
C4 O2 C1 C2 178.93(12) .
O1 C1 C2 C3 2.0(2) .
O2 C1 C2 C3 -178.11(14) .
C1 C2 C3 C3 -178.97(18) 3_766
C1 O2 C4 C5 -80.47(17) .
O2 C4 C5 C10 -73.28(19) .
O2 C4 C5 C6 107.18(17) .
C10 C5 C6 C7 -0.1(2) .
C4 C5 C6 C7 179.48(15) .
C5 C6 C7 C8 0.5(2) .
C5 C6 C7 O3 -178.74(17) .
C11 O3 C7 C6 -172.56(19) .
C11 O3 C7 C8 8.1(2) .
C6 C7 C8 C9 -0.5(3) .
O3 C7 C8 C9 178.87(17) .
C6 C7 C8 O4 -179.16(16) .
O3 C7 C8 O4 0.2(2) .
C11 O4 C8 C9 172.98(19) .
C11 O4 C8 C7 -8.5(2) .
C7 C8 C9 C10 0.0(3) .
O4 C8 C9 C10 178.44(18) .
C6 C5 C10 C9 -0.4(3) .
C4 C5 C10 C9 -179.93(17) .
C8 C9 C10 C5 0.4(3) .
C8 O4 C11 O3 13.4(2) .
C7 O3 C11 O4 -13.3(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101740203
