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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/51/1505146.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_1505146
loop_
_publ_author_name
'Furukawa, Daisuke'
'Matsumoto, Akikazu'
_publ_section_title
;
 Reaction Mechanism Based on X-ray Crystal Structure Analysis during the
 Solid-State Polymerization of Muconic Esters
;
_journal_issue                   17
_journal_name_full               Macromolecules
_journal_page_first              6048
_journal_paper_doi               10.1021/ma070802f
_journal_volume                  40
_journal_year                    2007
_chemical_formula_moiety         'C22 H22 O6'
_chemical_formula_sum            'C22 H22 O6'
_chemical_formula_weight         382.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 99.59(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   35.40(3)
_cell_length_b                   5.677(4)
_cell_length_c                   9.614(8)
_cell_measurement_reflns_used    6000
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.5
_cell_volume                     1905(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      123(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  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8425
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0788P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                1451
_reflns_number_total             2199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ma070802fsi20070626_070126.cif
_cod_data_source_block           10m
_cod_database_code               1505146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.57737(4) 0.2516(2) -0.16265(15) 0.0361(4) Uani 1 1 d . . .
O3 O 0.71724(4) 0.3093(2) 0.34539(14) 0.0357(4) Uani 1 1 d . . .
O1M O 0.5422(2) 0.0058(14) -0.3139(8) 0.0513(18) Uani 0.802(15) 1 d P A 1
C1M C 0.5070(2) 0.4045(13) -0.4626(8) 0.049(2) Uani 0.802(15) 1 d P . 1
H1M H 0.4970 0.2551 -0.4944 0.058 Uiso 0.802(15) 1 calc PR A 1
C2M C 0.53429(11) 0.4095(5) -0.3459(4) 0.0279(10) Uani 0.802(15) 1 d P A 1
H2M H 0.5428 0.5585 -0.3082 0.033 Uiso 0.802(15) 1 calc PR A 1
C3M C 0.55135(15) 0.1973(7) -0.2745(4) 0.0260(9) Uani 0.802(15) 1 d P A 1
O1P O 0.5444(7) -0.015(6) -0.307(3) 0.026(4) Uiso 0.198(15) 1 d P A 2
C1P C 0.5093(5) 0.390(3) -0.4658(18) 0.002(3) Uiso 0.198(15) 1 d P . 2
H1P H 0.5157 0.2541 -0.5146 0.002 Uiso 0.198(15) 1 calc PR A 2
C2P C 0.5167(8) 0.422(2) -0.299(2) 0.051(7) Uani 0.198(15) 1 d P . 2
H2P H 0.5323 0.5686 -0.2761 0.061 Uiso 0.198(15) 1 calc PR A 2
C3P C 0.5424(8) 0.220(5) -0.266(3) 0.064(10) Uiso 0.198(15) 1 d P A 2
C4 C 0.59601(6) 0.0506(3) -0.0888(2) 0.0363(5) Uani 1 1 d . A .
H1 H 0.6067 -0.0523 -0.1558 0.044 Uiso 1 1 calc R . .
H2 H 0.5772 -0.0419 -0.0461 0.044 Uiso 1 1 calc R . .
C5 C 0.62750(5) 0.1336(3) 0.0240(2) 0.0310(5) Uani 1 1 d . . .
C6 C 0.62512(6) 0.3382(3) 0.1018(2) 0.0337(5) Uani 1 1 d . A .
H3 H 0.6031 0.4353 0.0803 0.040 Uiso 1 1 calc R . .
C7 C 0.65415(5) 0.4034(3) 0.2097(2) 0.0320(5) Uani 1 1 d . . .
H4 H 0.6519 0.5433 0.2618 0.038 Uiso 1 1 calc R A .
C8 C 0.68661(5) 0.2641(3) 0.24145(19) 0.0289(4) Uani 1 1 d . A .
C9 C 0.68963(6) 0.0586(3) 0.1646(2) 0.0322(5) Uani 1 1 d . . .
H5 H 0.7117 -0.0382 0.1861 0.039 Uiso 1 1 calc R A .
C10 C 0.66051(6) -0.0033(3) 0.0575(2) 0.0329(5) Uani 1 1 d . A .
H6 H 0.6629 -0.1428 0.0051 0.039 Uiso 1 1 calc R . .
C11 C 0.71536(6) 0.5168(3) 0.4286(2) 0.0382(5) Uani 1 1 d . . .
H7 H 0.7155 0.6565 0.3688 0.046 Uiso 1 1 calc R . .
H8 H 0.7375 0.5214 0.5047 0.046 Uiso 1 1 calc R . .
H9 H 0.6917 0.5145 0.4691 0.046 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
C3M O2 C4 114.3(2) . .
C3M O2 C3P 13.9(12) . .
C4 O2 C3P 120.0(12) . .
C8 O3 C11 117.15(15) . .
C1M C1M C2M 125.0(10) 5_664 .
C1M C1M H1M 117.5 5_664 .
C2M C1M H1M 117.5 . .
C1M C2M C3M 123.5(4) . .
C1M C2M H2M 118.2 . .
C3M C2M H2M 118.2 . .
O1M C3M O2 126.2(5) . .
O1M C3M C2M 122.5(5) . .
O2 C3M C2M 111.3(3) . .
C1P C1P C2P 109.3(18) 5_664 .
C1P C1P H1P 125.3 5_664 .
C2P C1P H1P 125.3 . .
C3P C2P C1P 96.8(19) . .
C3P C2P C2P 111.2(16) . 2_654
C1P C2P C2P 124.4(18) . 2_654
C3P C2P H2P 107.7 . .
C1P C2P H2P 107.7 . .
C2P C2P H2P 107.7 2_654 .
O1P C3P O2 104(2) . .
O1P C3P C2P 138(3) . .
O2 C3P C2P 118(2) . .
O2 C4 C5 109.38(15) . .
O2 C4 H1 109.8 . .
C5 C4 H1 109.8 . .
O2 C4 H2 109.8 . .
C5 C4 H2 109.8 . .
H1 C4 H2 108.2 . .
C6 C5 C10 117.67(18) . .
C6 C5 C4 123.22(18) . .
C10 C5 C4 119.07(17) . .
C7 C6 C5 121.48(18) . .
C7 C6 H3 119.3 . .
C5 C6 H3 119.3 . .
C6 C7 C8 119.84(18) . .
C6 C7 H4 120.1 . .
C8 C7 H4 120.1 . .
O3 C8 C7 125.45(17) . .
O3 C8 C9 114.94(17) . .
C7 C8 C9 119.62(18) . .
C10 C9 C8 119.77(18) . .
C10 C9 H5 120.1 . .
C8 C9 H5 120.1 . .
C9 C10 C5 121.62(18) . .
C9 C10 H6 119.2 . .
C5 C10 H6 119.2 . .
O3 C11 H7 109.5 . .
O3 C11 H8 109.5 . .
H7 C11 H8 109.5 . .
O3 C11 H9 109.5 . .
H7 C11 H9 109.5 . .
H8 C11 H9 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C3M 1.331(4) .
O2 C4 1.444(2) .
O2 C3P 1.46(3) .
O3 C8 1.371(2) .
O3 C11 1.432(2) .
O1M C3M 1.179(10) .
C1M C1M 1.349(15) 5_664
C1M C2M 1.353(9) .
C1M H1M 0.9500 .
C2M C3M 1.466(5) .
C2M H2M 0.9500 .
O1P C3P 1.39(5) .
C1P C1P 1.51(4) 5_664
C1P C2P 1.60(3) .
C1P H1P 0.9500 .
C2P C3P 1.47(3) .
C2P C2P 1.63(7) 2_654
C2P H2P 1.0000 .
C4 C5 1.496(3) .
C4 H1 0.9900 .
C4 H2 0.9900 .
C5 C6 1.392(3) .
C5 C10 1.396(3) .
C6 C7 1.383(3) .
C6 H3 0.9500 .
C7 C8 1.386(3) .
C7 H4 0.9500 .
C8 C9 1.395(3) .
C9 C10 1.376(3) .
C9 H5 0.9500 .
C10 H6 0.9500 .
C11 H7 0.9800 .
C11 H8 0.9800 .
C11 H9 0.9800 .
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
C1M C1M C2M C3M -174.4(8) 5_664 .
C4 O2 C3M O1M 1.9(8) . .
C3P O2 C3M O1M -115(6) . .
C4 O2 C3M C2M -178.7(3) . .
C3P O2 C3M C2M 64(5) . .
C1M C2M C3M O1M -0.6(8) . .
C1M C2M C3M O2 -180.0(7) . .
C1P C1P C2P C3P -167(2) 5_664 .
C1P C1P C2P C2P 72(2) 5_664 2_654
C3M O2 C3P O1P 46(4) . .
C4 O2 C3P O1P -23(2) . .
C3M O2 C3P C2P -133(7) . .
C4 O2 C3P C2P 157.4(18) . .
C1P C2P C3P O1P -44(4) . .
C2P C2P C3P O1P 87(4) 2_654 .
C1P C2P C3P O2 135(2) . .
C2P C2P C3P O2 -94(2) 2_654 .
C3M O2 C4 C5 173.6(3) . .
C3P O2 C4 C5 -172.1(13) . .
O2 C4 C5 C6 35.7(3) . .
O2 C4 C5 C10 -146.63(18) . .
C10 C5 C6 C7 -0.7(3) . .
C4 C5 C6 C7 177.00(19) . .
C5 C6 C7 C8 0.4(3) . .
C11 O3 C8 C7 0.5(3) . .
C11 O3 C8 C9 -179.29(16) . .
C6 C7 C8 O3 -179.98(18) . .
C6 C7 C8 C9 -0.2(3) . .
O3 C8 C9 C10 -179.89(16) . .
C7 C8 C9 C10 0.3(3) . .
C8 C9 C10 C5 -0.6(3) . .
C6 C5 C10 C9 0.8(3) . .
C4 C5 C10 C9 -177.00(18) . .
