#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:22:48 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179575 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/40/4504009.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_4504009
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
_chemical_name_systematic
; 
 ? 
;
_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                 92.85(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.990(5)
_cell_length_b                   4.855(3)
_cell_length_c                   31.941(14)
_cell_measurement_reflns_used    4593
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.4
_cell_volume                     927.7(10)
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0505
_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       -41
_diffrn_reflns_number            2120
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1634
_refine_ls_R_factor_gt           0.0948
_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)+(0.1737P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2820
_refine_ls_wR_factor_ref         0.3172
_reflns_number_gt                1073
_reflns_number_total             2120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0606444si20070319_011037.cif
_cod_data_source_block           poly(4NO2)
_cod_original_cell_volume        927.8(10)
_cod_database_code               4504009
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 0.1964(8) 0.5965(10) 0.55882(13) 0.120(2) Uani 1 1 d .
O2 O 0.5074(6) 0.3833(6) 0.58158(9) 0.0633(10) Uani 1 1 d .
O3 O 0.8350(6) -0.6169(6) 0.73878(10) 0.0642(10) Uani 1 1 d .
O4 O 1.0997(6) -0.5750(7) 0.69603(10) 0.0731(11) Uani 1 1 d .
N1 N 0.9171(6) -0.5154(7) 0.70805(10) 0.0516(9) Uani 1 1 d .
C1 C 0.3826(11) 0.5342(10) 0.55421(15) 0.0736(16) Uani 1 1 d .
C2 C 0.5163(10) 0.6179(9) 0.51744(14) 0.0707(15) Uani 1 1 d .
H2 H 0.6748 0.6306 0.5264 0.085 Uiso 1 1 calc R
C3 C 0.4366(11) 0.8931(8) 0.50110(14) 0.0739(16) Uani 1 1 d .
H3 H 0.2873 0.9101 0.4921 0.089 Uiso 1 1 calc R
C4 C 0.3909(9) 0.2733(9) 0.61591(13) 0.0603(13) Uani 1 1 d .
H4A H 0.2560 0.1805 0.6054 0.072 Uiso 1 1 calc R
H4B H 0.3483 0.4214 0.6343 0.072 Uiso 1 1 calc R
C5 C 0.5395(8) 0.0737(8) 0.63980(12) 0.0535(11) Uani 1 1 d .
C6 C 0.4689(8) -0.0267(9) 0.67754(12) 0.0563(12) Uani 1 1 d .
H6 H 0.3352 0.0364 0.6876 0.068 Uiso 1 1 calc R
C7 C 0.5915(8) -0.2159(8) 0.70007(12) 0.0527(11) Uani 1 1 d .
H7 H 0.5437 -0.2813 0.7255 0.063 Uiso 1 1 calc R
C8 C 0.7876(7) -0.3082(8) 0.68443(12) 0.0461(10) Uani 1 1 d .
C9 C 0.8603(8) -0.2114(10) 0.64699(14) 0.0605(13) Uani 1 1 d .
H9 H 0.9940 -0.2754 0.6370 0.073 Uiso 1 1 calc R
C10 C 0.7375(8) -0.0230(10) 0.62468(13) 0.0626(13) Uani 1 1 d .
H10 H 0.7860 0.0413 0.5993 0.075 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 115.2(4) . .
O4 N1 O3 124.3(4) . .
O4 N1 C8 117.8(3) . .
O3 N1 C8 118.0(3) . .
O1 C1 O2 124.3(4) . .
O1 C1 C2 125.0(5) . .
O2 C1 C2 110.7(5) . .
C3 C2 C1 109.7(4) . .
C3 C2 C2 111.6(5) . 3_666
C1 C2 C2 107.3(5) . 3_666
C3 C2 H2 109.4 . .
C1 C2 H2 109.4 . .
C2 C2 H2 109.4 3_666 .
C3 C3 C2 123.8(8) 3_676 .
C3 C3 H3 118.1 3_676 .
C2 C3 H3 118.1 . .
O2 C4 C5 109.3(4) . .
O2 C4 H4A 109.8 . .
C5 C4 H4A 109.8 . .
O2 C4 H4B 109.8 . .
C5 C4 H4B 109.8 . .
H4A C4 H4B 108.3 . .
C10 C5 C6 119.2(4) . .
C10 C5 C4 122.6(4) . .
C6 C5 C4 118.1(4) . .
C7 C6 C5 121.2(4) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C8 118.5(4) . .
C6 C7 H7 120.8 . .
C8 C7 H7 120.8 . .
C7 C8 C9 121.2(4) . .
C7 C8 N1 118.6(4) . .
C9 C8 N1 120.2(4) . .
C10 C9 C8 120.0(4) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C5 119.9(4) . .
C9 C10 H10 120.1 . .
C5 C10 H10 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.172(6) .
O2 C1 1.340(6) .
O2 C4 1.432(5) .
O3 N1 1.223(4) .
O4 N1 1.212(4) .
N1 C8 1.458(5) .
C1 C2 1.510(7) .
C2 C3 1.503(6) .
C2 C2 1.602(10) 3_666
C2 H2 0.9800 .
C3 C3 1.290(10) 3_676
C3 H3 0.9300 .
C4 C5 1.498(6) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C10 1.385(6) .
C5 C6 1.386(5) .
C6 C7 1.359(6) .
C6 H6 0.9300 .
C7 C8 1.375(6) .
C7 H7 0.9300 .
C8 C9 1.376(6) .
C9 C10 1.354(6) .
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_1
_geom_torsion_site_symmetry_4
C4 O2 C1 O1 6.5(8) . .
C4 O2 C1 C2 -174.9(4) . .
O1 C1 C2 C3 30.2(9) . .
O2 C1 C2 C3 -148.4(5) . .
O1 C1 C2 C2 -91.2(8) . 3_666
O2 C1 C2 C2 90.2(6) . 3_666
C1 C2 C3 C3 121.4(7) . 3_676
C2 C2 C3 C3 -119.8(7) 3_666 3_676
C1 O2 C4 C5 170.8(4) . .
O2 C4 C5 C10 -11.9(6) . .
O2 C4 C5 C6 171.3(4) . .
C10 C5 C6 C7 0.7(7) . .
C4 C5 C6 C7 177.6(4) . .
C5 C6 C7 C8 -0.5(7) . .
C6 C7 C8 C9 0.4(7) . .
C6 C7 C8 N1 -178.7(4) . .
O4 N1 C8 C7 -173.0(4) . .
O3 N1 C8 C7 6.7(6) . .
O4 N1 C8 C9 7.9(6) . .
O3 N1 C8 C9 -172.4(4) . .
C7 C8 C9 C10 -0.4(8) . .
N1 C8 C9 C10 178.7(4) . .
C8 C9 C10 C5 0.5(8) . .
C6 C5 C10 C9 -0.7(8) . .
C4 C5 C10 C9 -177.4(4) . .
