#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:40:50 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244557 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/91/7239123.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_7239123
loop_
_publ_author_name
'Thiyagarajan, Shanmugam'
'Pukin, Aliaksei'
'van Haveren, Jacco'
'Lutz, Martin'
'van Es, Daan S.'
_publ_section_title
;
 Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid:
 unexpected aspects of the Henkel reaction
;
_journal_issue                   36
_journal_name_full               'RSC Adv.'
_journal_page_first              15678
_journal_paper_doi               10.1039/C3RA42457J
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C8 H8 O5'
_chemical_formula_sum            'C8 H8 O5'
_chemical_formula_weight         184.14
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.294(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.2706(19)
_cell_length_b                   11.0750(13)
_cell_length_c                   11.6658(14)
_cell_measurement_reflns_used    6857
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.42
_cell_volume                     1667.8(4)
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_collection       Apex2
_computing_data_reduction        'SAINT V7.68A, SADABS-2008/1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14085
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0671P)²+1.6627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                1315
_reflns_number_total             1563
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ra42457j.txt
_cod_data_source_block           l0374a
_cod_original_cell_volume        1667.8(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7239123
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
O1 O 0.39182(10) 0.24879(11) 0.01424(13) 0.0293(3) Uani 1 1 d .
O2 O 0.38484(11) 0.01836(12) 0.09882(13) 0.0355(4) Uani 1 1 d .
O3 O 0.35546(11) 0.09680(11) 0.25325(12) 0.0307(3) Uani 1 1 d .
O4 O 0.37398(11) 0.60397(12) 0.20246(14) 0.0359(4) Uani 1 1 d .
O5 O 0.38499(11) 0.62171(11) 0.01813(13) 0.0323(4) Uani 1 1 d .
C1 C 0.37316(13) 0.10329(15) 0.15327(17) 0.0256(4) Uani 1 1 d .
C2 C 0.37613(13) 0.23013(16) 0.11831(17) 0.0244(4) Uani 1 1 d .
C3 C 0.36740(13) 0.33666(15) 0.16791(17) 0.0250(4) Uani 1 1 d .
H3 H 0.3561 0.3483 0.2397 0.030 Uiso 1 1 calc R
C4 C 0.37867(13) 0.42807(16) 0.09059(17) 0.0252(4) Uani 1 1 d .
C5 C 0.39273(14) 0.37024(16) -0.00051(18) 0.0286(4) Uani 1 1 d .
H5 H 0.4020 0.4093 -0.0658 0.034 Uiso 1 1 calc R
C6 C 0.35321(18) -0.02495(17) 0.2981(2) 0.0370(5) Uani 1 1 d .
H6A H 0.3001 -0.0723 0.2212 0.055 Uiso 1 1 calc R
H6B H 0.3370 -0.0216 0.3688 0.055 Uiso 1 1 calc R
H6C H 0.4210 -0.0630 0.3347 0.055 Uiso 1 1 calc R
C7 C 0.37852(13) 0.55899(16) 0.11175(17) 0.0259(4) Uani 1 1 d .
C8 C 0.39205(17) 0.75194(16) 0.0357(2) 0.0384(5) Uani 1 1 d .
H8A H 0.3313 0.7816 0.0350 0.058 Uiso 1 1 calc R
H8B H 0.3946 0.7896 -0.0385 0.058 Uiso 1 1 calc R
H8C H 0.4550 0.7724 0.1225 0.058 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0461(8) 0.0213(7) 0.0311(7) 0.0001(5) 0.0277(6) 0.0011(5)
O2 0.0594(9) 0.0223(7) 0.0361(7) -0.0014(5) 0.0330(7) 0.0024(6)
O3 0.0513(8) 0.0214(7) 0.0299(7) 0.0010(5) 0.0286(6) -0.0002(5)
O4 0.0584(9) 0.0249(7) 0.0375(8) -0.0032(5) 0.0343(7) -0.0010(6)
O5 0.0543(9) 0.0187(7) 0.0312(7) 0.0023(5) 0.0277(6) -0.0001(5)
C1 0.0317(9) 0.0235(9) 0.0239(8) -0.0001(7) 0.0164(8) 0.0002(7)
C2 0.0281(9) 0.0250(9) 0.0226(9) 0.0009(7) 0.0151(8) 0.0009(7)
C3 0.0311(9) 0.0227(9) 0.0247(8) 0.0003(7) 0.0173(7) 0.0011(7)
C4 0.0301(9) 0.0217(9) 0.0263(9) 0.0012(7) 0.0167(7) 0.0010(7)
C5 0.0402(10) 0.0224(9) 0.0302(9) 0.0027(7) 0.0235(8) 0.0002(7)
C6 0.0611(13) 0.0234(9) 0.0366(10) 0.0041(8) 0.0329(10) -0.0029(9)
C7 0.0308(9) 0.0222(9) 0.0262(9) 0.0011(7) 0.0162(8) 0.0004(7)
C8 0.0594(13) 0.0180(10) 0.0454(12) 0.0015(8) 0.0330(11) -0.0015(8)
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
C5 O1 C2 106.24(13)
C1 O3 C6 114.85(14)
C7 O5 C8 115.54(14)
O2 C1 O3 125.30(16)
O2 C1 C2 124.51(16)
O3 C1 C2 110.19(14)
C3 C2 O1 110.55(15)
C3 C2 C1 133.67(16)
O1 C2 C1 115.78(15)
C2 C3 C4 106.02(15)
C2 C3 H3 127.0
C4 C3 H3 127.0
C5 C4 C3 106.51(15)
C5 C4 C7 127.86(16)
C3 C4 C7 125.59(15)
C4 C5 O1 110.67(15)
C4 C5 H5 124.7
O1 C5 H5 124.7
O3 C6 H6A 109.5
O3 C6 H6B 109.5
H6A C6 H6B 109.5
O3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O4 C7 O5 124.39(17)
O4 C7 C4 124.13(16)
O5 C7 C4 111.48(14)
O5 C8 H8A 109.5
O5 C8 H8B 109.5
H8A C8 H8B 109.5
O5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.357(2)
O1 C2 1.373(2)
O2 C1 1.200(2)
O3 C1 1.332(2)
O3 C6 1.454(2)
O4 C7 1.205(2)
O5 C7 1.342(2)
O5 C8 1.453(2)
C1 C2 1.470(2)
C2 C3 1.352(2)
C3 C4 1.426(2)
C3 H3 0.9500
C4 C5 1.353(2)
C4 C7 1.471(2)
C5 H5 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 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
C6 O3 C1 O2 1.4(3)
C6 O3 C1 C2 -178.71(15)
C5 O1 C2 C3 -0.01(19)
C5 O1 C2 C1 -179.52(15)
O2 C1 C2 C3 -178.25(19)
O3 C1 C2 C3 1.9(3)
O2 C1 C2 O1 1.1(3)
O3 C1 C2 O1 -178.73(14)
O1 C2 C3 C4 -0.22(19)
C1 C2 C3 C4 179.17(18)
C2 C3 C4 C5 0.4(2)
C2 C3 C4 C7 -177.60(16)
C3 C4 C5 O1 -0.4(2)
C7 C4 C5 O1 177.52(16)
C2 O1 C5 C4 0.3(2)
C8 O5 C7 O4 3.2(3)
C8 O5 C7 C4 -176.23(16)
C5 C4 C7 O4 -173.59(18)
C3 C4 C7 O4 3.9(3)
C5 C4 C7 O5 5.9(3)
C3 C4 C7 O5 -176.61(16)
