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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/4/50/40/4504006.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_4504006
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         'C20 H16 N2 O8 '
_chemical_formula_sum            'C20 H16 N2 O8'
_chemical_formula_weight         412.35
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.1720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.79950(10)
_cell_length_b                   5.23930(10)
_cell_length_c                   31.1930(2)
_cell_measurement_reflns_used    7002
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      0.7
_cell_volume                     947.61(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_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 0.940
_diffrn_measured_fraction_theta_max 0.940
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            5842
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_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          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0781
_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)+(0.0946P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                1307
_reflns_number_total             2053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0606444si20070319_010937.cif
_cod_data_source_block           4NO2
_cod_database_code               4504006
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_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 -0.2069(5) 0.7032(5) 0.56655(8) 0.0702(8) Uani 1 1 d .
O2 O 0.0874(4) 0.4496(4) 0.58366(6) 0.0468(6) Uani 1 1 d .
O3 O 0.3385(4) -0.5415(4) 0.73863(7) 0.0508(6) Uani 1 1 d .
O4 O 0.6261(4) -0.5041(4) 0.69696(8) 0.0570(7) Uani 1 1 d .
N1 N 0.4353(4) -0.4425(4) 0.70855(7) 0.0361(6) Uani 1 1 d .
C1 C -0.0132(6) 0.6373(6) 0.56127(9) 0.0444(8) Uani 1 1 d .
C2 C 0.1501(6) 0.7438(6) 0.53045(10) 0.0544(9) Uani 1 1 d .
H2 H 0.2973 0.6734 0.5303 0.065 Uiso 1 1 calc R
C3 C 0.1060(6) 0.9323(7) 0.50268(11) 0.0540(9) Uani 1 1 d .
H3 H 0.2258 0.9803 0.4850 0.065 Uiso 1 1 calc R
C4 C -0.0501(6) 0.3369(6) 0.61649(10) 0.0477(9) Uani 1 1 d .
H4A H -0.1862 0.2584 0.6036 0.057 Uiso 1 1 calc R
H4B H -0.0999 0.4680 0.6362 0.057 Uiso 1 1 calc R
C5 C 0.0889(5) 0.1391(5) 0.64042(9) 0.0346(7) Uani 1 1 d .
C6 C 0.0008(5) 0.0432(6) 0.67799(9) 0.0398(7) Uani 1 1 d .
H6 H -0.1369 0.1083 0.6881 0.048 Uiso 1 1 calc R
C7 C 0.1124(5) -0.1459(6) 0.70056(9) 0.0374(7) Uani 1 1 d .
H7 H 0.0517 -0.2104 0.7257 0.045 Uiso 1 1 calc R
C8 C 0.3160(5) -0.2376(5) 0.68513(8) 0.0318(6) Uani 1 1 d .
C9 C 0.4111(5) -0.1442(6) 0.64818(9) 0.0420(8) Uani 1 1 d .
H9 H 0.5503 -0.2076 0.6384 0.050 Uiso 1 1 calc R
C10 C 0.2954(6) 0.0451(6) 0.62614(9) 0.0436(8) Uani 1 1 d .
H10 H 0.3574 0.1107 0.6012 0.052 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'
N N 0.0061 0.0033 '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 115.7(3) . .
O4 N1 O3 123.6(3) . .
O4 N1 C8 118.1(3) . .
O3 N1 C8 118.4(3) . .
O1 C1 O2 123.1(3) . .
O1 C1 C2 127.0(3) . .
O2 C1 C2 109.9(3) . .
C3 C2 C1 125.9(3) . .
C3 C2 H2 117.0 . .
C1 C2 H2 117.0 . .
C2 C3 C3 126.7(4) . 3_576
C2 C3 H3 116.7 . .
C3 C3 H3 116.7 3_576 .
O2 C4 C5 109.7(3) . .
O2 C4 H4A 109.7 . .
C5 C4 H4A 109.7 . .
O2 C4 H4B 109.7 . .
C5 C4 H4B 109.7 . .
H4A C4 H4B 108.2 . .
C10 C5 C6 118.9(3) . .
C10 C5 C4 123.2(3) . .
C6 C5 C4 117.9(3) . .
C7 C6 C5 121.3(3) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C8 118.3(3) . .
C6 C7 H7 120.9 . .
C8 C7 H7 120.9 . .
C7 C8 C9 122.1(3) . .
C7 C8 N1 118.9(3) . .
C9 C8 N1 119.0(3) . .
C10 C9 C8 118.4(3) . .
C10 C9 H9 120.8 . .
C8 C9 H9 120.8 . .
C9 C10 C5 121.0(3) . .
C9 C10 H10 119.5 . .
C5 C10 H10 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.190(4) .
O2 C1 1.333(4) .
O2 C4 1.437(4) .
O3 N1 1.219(3) .
O4 N1 1.214(3) .
N1 C8 1.465(4) .
C1 C2 1.473(5) .
C2 C3 1.335(4) .
C2 H2 0.9300 .
C3 C3 1.426(7) 3_576
C3 H3 0.9300 .
C4 C5 1.502(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C10 1.377(4) .
C5 C6 1.383(4) .
C6 C7 1.370(4) .
C6 H6 0.9300 .
C7 C8 1.371(4) .
C7 H7 0.9300 .
C8 C9 1.378(4) .
C9 C10 1.374(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
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 -2.8(5) .
C4 O2 C1 C2 177.1(3) .
O1 C1 C2 C3 -0.9(6) .
O2 C1 C2 C3 179.3(3) .
C1 C2 C3 C3 0.1(7) 3_576
C1 O2 C4 C5 -177.0(3) .
O2 C4 C5 C10 -13.3(4) .
O2 C4 C5 C6 168.5(3) .
C10 C5 C6 C7 -1.3(5) .
C4 C5 C6 C7 177.0(3) .
C5 C6 C7 C8 0.4(5) .
C6 C7 C8 C9 0.6(5) .
C6 C7 C8 N1 -179.0(3) .
O4 N1 C8 C7 -172.8(3) .
O3 N1 C8 C7 7.0(4) .
O4 N1 C8 C9 7.6(4) .
O3 N1 C8 C9 -172.6(3) .
C7 C8 C9 C10 -0.7(5) .
N1 C8 C9 C10 178.9(3) .
C8 C9 C10 C5 -0.2(5) .
C6 C5 C10 C9 1.2(5) .
C4 C5 C10 C9 -177.0(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15717654
