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#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/03/7060344.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_7060344
loop_
_publ_author_name
'Kvyatkovskaya, Elizaveta A.'
'Epifanova, Polina P.'
'Nikitina, Eugeniya V.'
'Senin, Aleksey A.'
'Khrustalev, Victor N.'
'Polyanskii, Kirill B.'
'Zubkov, Fedor I.'
_publ_section_title
;
 Synthesis and ethylene-promoted metathesis of adducts of tandem
 [4+2]/[4+2] cycloaddition between bis-furyl dienes and maleic acid
 derivatives
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3400
_journal_page_last               3407
_journal_paper_doi               10.1039/D0NJ04528D
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H12 O6'
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-08-30 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.4540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6953(2)
_cell_length_b                   10.0575(2)
_cell_length_c                   11.2520(2)
_cell_measurement_reflns_used    6677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.57
_cell_measurement_theta_min      3.01
_cell_volume                     1110.36(4)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12197
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.579
_diffrn_reflns_theta_min         3.008
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 1819 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²+0.2749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3854
_reflns_number_total             4021
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj04528d2.cif
_cod_data_source_block           3f
_cod_depositor_comments
'Adding full bibliography for 7060344--7060348.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7060344
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.67120(15) 0.64091(14) 0.51358(14) 0.0123(2) Uani 1 1 d . . . . .
H1A H 0.7038 0.6991 0.5910 0.015 Uiso 1 1 calc R U . . .
H1B H 0.7491 0.5864 0.5156 0.015 Uiso 1 1 calc R U . . .
O2 O 0.62310(11) 0.72175(10) 0.39879(11) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.51284(16) 0.80710(14) 0.39023(16) 0.0135(2) Uani 1 1 d . . . . .
H3A H 0.4862 0.8623 0.3111 0.016 Uiso 1 1 calc R U . . .
H3B H 0.5430 0.8674 0.4660 0.016 Uiso 1 1 calc R U . . .
C3A C 0.39176(14) 0.72812(13) 0.38610(13) 0.0103(2) Uani 1 1 d . . . . .
C4 C 0.26265(15) 0.79580(14) 0.38086(14) 0.0127(2) Uani 1 1 d . . . . .
H4 H 0.2539 0.8839 0.4071 0.015 Uiso 1 1 calc R U . . .
C5 C 0.16390(16) 0.70510(15) 0.33148(14) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.0704 0.7150 0.3163 0.016 Uiso 1 1 calc R U . . .
C6 C 0.23216(14) 0.58283(15) 0.30470(14) 0.0117(2) Uani 1 1 d . . . . .
H6 H 0.1700 0.5210 0.2375 0.014 Uiso 1 1 calc R U . . .
O6 O 0.33788(10) 0.64317(10) 0.27346(10) 0.01103(19) Uani 1 1 d . . . . .
C6A C 0.31648(14) 0.51805(13) 0.43862(13) 0.0100(2) Uani 1 1 d . . . . .
H6A H 0.2614 0.5018 0.4911 0.012 Uiso 1 1 calc R U . . .
C7 C 0.40541(14) 0.39845(13) 0.43729(13) 0.0100(2) Uani 1 1 d . . . . .
H7 H 0.3552 0.3267 0.3751 0.012 Uiso 1 1 calc R U . . .
O7 O 0.51749(10) 0.45492(10) 0.41359(9) 0.00985(18) Uani 1 1 d . . . . .
C7A C 0.47871(15) 0.35101(14) 0.57905(13) 0.0109(2) Uani 1 1 d . . . . .
H7A H 0.4159 0.3448 0.6251 0.013 Uiso 1 1 calc R U . . .
C8 C 0.55768(16) 0.22464(15) 0.58836(14) 0.0139(3) Uani 1 1 d . . . . .
O8 O 0.51663(14) 0.11489(11) 0.55437(12) 0.0199(2) Uani 1 1 d . . . . .
O9 O 0.69698(12) 0.24918(11) 0.64564(11) 0.0150(2) Uani 1 1 d . . . . .
C10 C 0.72207(16) 0.38318(15) 0.67672(15) 0.0152(3) Uani 1 1 d . . . . .
O10 O 0.83617(13) 0.42234(13) 0.72617(14) 0.0246(3) Uani 1 1 d . . . . .
C10A C 0.58958(14) 0.45840(14) 0.63729(13) 0.0115(2) Uani 1 1 d . . . . .
H10A H 0.5812 0.5061 0.7117 0.014 Uiso 1 1 calc R U . . .
C10B C 0.56007(14) 0.55039(13) 0.51828(13) 0.0095(2) Uani 1 1 d . . . . .
C10C C 0.42864(14) 0.62574(14) 0.49882(13) 0.0093(2) Uani 1 1 d . . . . .
H10C H 0.4291 0.6650 0.5806 0.011 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
O2 C1 C10B 111.49(11) . . ?
O2 C1 H1A 109.3 . . ?
C10B C1 H1A 109.3 . . ?
O2 C1 H1B 109.3 . . ?
C10B C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 O2 C1 112.99(11) . . ?
O2 C3 C3A 111.21(11) . . ?
O2 C3 H3A 109.4 . . ?
C3A C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
C3A C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O6 C3A C3 112.16(12) . . ?
O6 C3A C4 101.06(11) . . ?
C3 C3A C4 121.51(11) . . ?
O6 C3A C10C 101.93(10) . . ?
C3 C3A C10C 112.83(11) . . ?
C4 C3A C10C 105.04(11) . . ?
C5 C4 C3A 105.41(12) . . ?
C5 C4 H4 127.3 . . ?
C3A C4 H4 127.3 . . ?
C4 C5 C6 105.77(13) . . ?
C4 C5 H5 127.1 . . ?
C6 C5 H5 127.1 . . ?
O6 C6 C5 101.11(12) . . ?
O6 C6 C6A 101.73(10) . . ?
C5 C6 C6A 106.58(11) . . ?
O6 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C6A C6 H6 115.2 . . ?
C6 O6 C3A 96.46(10) . . ?
C7 C6A C10C 100.14(10) . . ?
C7 C6A C6 116.11(11) . . ?
C10C C6A C6 100.31(10) . . ?
C7 C6A H6A 112.9 . . ?
C10C C6A H6A 112.9 . . ?
C6 C6A H6A 112.9 . . ?
O7 C7 C6A 104.85(10) . . ?
O7 C7 C7A 101.22(11) . . ?
C6A C7 C7A 107.04(11) . . ?
O7 C7 H7 114.2 . . ?
C6A C7 H7 114.2 . . ?
C7A C7 H7 114.2 . . ?
C7 O7 C10B 97.25(10) . . ?
C8 C7A C10A 104.24(12) . . ?
C8 C7A C7 111.84(12) . . ?
C10A C7A C7 102.14(11) . . ?
C8 C7A H7A 112.6 . . ?
C10A C7A H7A 112.6 . . ?
C7 C7A H7A 112.6 . . ?
O8 C8 O9 120.18(14) . . ?
O8 C8 C7A 129.31(15) . . ?
O9 C8 C7A 110.50(13) . . ?
C8 O9 C10 110.64(12) . . ?
O10 C10 O9 119.86(14) . . ?
O10 C10 C10A 129.82(15) . . ?
O9 C10 C10A 110.31(13) . . ?
C10 C10A C7A 104.29(12) . . ?
C10 C10A C10B 113.39(12) . . ?
C7A C10A C10B 101.11(11) . . ?
C10 C10A H10A 112.4 . . ?
C7A C10A H10A 112.4 . . ?
C10B C10A H10A 112.4 . . ?
O7 C10B C1 111.58(11) . . ?
O7 C10B C10C 103.78(10) . . ?
C1 C10B C10C 112.66(11) . . ?
O7 C10B C10A 101.35(10) . . ?
C1 C10B C10A 119.68(12) . . ?
C10C C10B C10A 106.12(11) . . ?
C10B C10C C6A 102.82(11) . . ?
C10B C10C C3A 111.32(11) . . ?
C6A C10C C3A 101.77(10) . . ?
C10B C10C H10C 113.3 . . ?
C6A C10C H10C 113.3 . . ?
C3A C10C H10C 113.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.4370(18) . ?
C1 C10B 1.515(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C3 1.4305(18) . ?
C3 C3A 1.504(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O6 1.4447(17) . ?
C3A C4 1.519(2) . ?
C3A C10C 1.5576(19) . ?
C4 C5 1.338(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.520(2) . ?
C5 H5 0.9500 . ?
C6 O6 1.4445(17) . ?
C6 C6A 1.5578(19) . ?
C6 H6 1.0000 . ?
C6A C7 1.5372(19) . ?
C6A C10C 1.5569(19) . ?
C6A H6A 1.0000 . ?
C7 O7 1.4439(17) . ?
C7 C7A 1.5464(19) . ?
C7 H7 1.0000 . ?
O7 C10B 1.4457(16) . ?
C7A C8 1.506(2) . ?
C7A C10A 1.544(2) . ?
C7A H7A 1.0000 . ?
C8 O8 1.1932(19) . ?
C8 O9 1.3898(19) . ?
O9 C10 1.3913(19) . ?
C10 O10 1.189(2) . ?
C10 C10A 1.509(2) . ?
C10A C10B 1.553(2) . ?
C10A H10A 1.0000 . ?
C10B C10C 1.5340(19) . ?
C10C H10C 1.0000 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A O6 0.99 2.54 3.5064(17) 165.5 4_565
C6 H6 O8 1.00 2.47 3.4690(18) 174.0 4_454
C7 H7 O9 1.00 2.58 3.4814(18) 150.5 4_454
C7A H7A O6 1.00 2.15 3.1113(17) 161.5 2_565
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10B C1 O2 C3 60.84(15) . . . . ?
C1 O2 C3 C3A -60.96(16) . . . . ?
O2 C3 C3A O6 -62.25(15) . . . . ?
O2 C3 C3A C4 178.23(12) . . . . ?
O2 C3 C3A C10C 52.19(16) . . . . ?
O6 C3A C4 C5 33.16(14) . . . . ?
C3 C3A C4 C5 157.96(14) . . . . ?
C10C C3A C4 C5 -72.54(14) . . . . ?
C3A C4 C5 C6 -0.82(15) . . . . ?
C4 C5 C6 O6 -31.77(14) . . . . ?
C4 C5 C6 C6A 74.17(15) . . . . ?
C5 C6 O6 C3A 50.62(12) . . . . ?
C6A C6 O6 C3A -59.12(11) . . . . ?
C3 C3A O6 C6 177.92(11) . . . . ?
C4 C3A O6 C6 -51.19(12) . . . . ?
C10C C3A O6 C6 56.96(12) . . . . ?
O6 C6 C6A C7 -69.33(13) . . . . ?
C5 C6 C6A C7 -174.82(11) . . . . ?
O6 C6 C6A C10C 37.44(12) . . . . ?
C5 C6 C6A C10C -68.05(14) . . . . ?
C10C C6A C7 O7 -33.78(12) . . . . ?
C6 C6A C7 O7 73.09(14) . . . . ?
C10C C6A C7 C7A 73.19(12) . . . . ?
C6 C6A C7 C7A -179.94(11) . . . . ?
C6A C7 O7 C10B 53.93(12) . . . . ?
C7A C7 O7 C10B -57.27(11) . . . . ?
O7 C7 C7A C8 -76.57(13) . . . . ?
C6A C7 C7A C8 173.91(12) . . . . ?
O7 C7 C7A C10A 34.37(12) . . . . ?
C6A C7 C7A C10A -75.15(13) . . . . ?
C10A C7A C8 O8 -179.09(16) . . . . ?
C7 C7A C8 O8 -69.5(2) . . . . ?
C10A C7A C8 O9 0.79(15) . . . . ?
C7 C7A C8 O9 110.40(13) . . . . ?
O8 C8 O9 C10 179.58(14) . . . . ?
C7A C8 O9 C10 -0.31(16) . . . . ?
C8 O9 C10 O10 -179.68(15) . . . . ?
C8 O9 C10 C10A -0.33(16) . . . . ?
O10 C10 C10A C7A -179.93(18) . . . . ?
O9 C10 C10A C7A 0.80(15) . . . . ?
O10 C10 C10A C10B 71.0(2) . . . . ?
O9 C10 C10A C10B -108.27(14) . . . . ?
C8 C7A C10A C10 -0.92(14) . . . . ?
C7 C7A C10A C10 -117.49(12) . . . . ?
C8 C7A C10A C10B 116.95(12) . . . . ?
C7 C7A C10A C10B 0.38(13) . . . . ?
C7 O7 C10B C1 -173.79(11) . . . . ?
C7 O7 C10B C10C -52.22(12) . . . . ?
C7 O7 C10B C10A 57.71(11) . . . . ?
O2 C1 C10B O7 64.29(15) . . . . ?
O2 C1 C10B C10C -51.99(15) . . . . ?
O2 C1 C10B C10A -177.73(11) . . . . ?
C10 C10A C10B O7 76.03(14) . . . . ?
C7A C10A C10B O7 -35.00(13) . . . . ?
C10 C10A C10B C1 -47.08(17) . . . . ?
C7A C10A C10B C1 -158.11(12) . . . . ?
C10 C10A C10B C10C -175.85(11) . . . . ?
C7A C10A C10B C10C 73.12(12) . . . . ?
O7 C10B C10C C6A 31.47(13) . . . . ?
C1 C10B C10C C6A 152.32(11) . . . . ?
C10A C10B C10C C6A -74.91(12) . . . . ?
O7 C10B C10C C3A -76.80(13) . . . . ?
C1 C10B C10C C3A 44.05(15) . . . . ?
C10A C10B C10C C3A 176.83(10) . . . . ?
C7 C6A C10C C10B 1.18(13) . . . . ?
C6 C6A C10C C10B -117.96(11) . . . . ?
C7 C6A C10C C3A 116.54(11) . . . . ?
C6 C6A C10C C3A -2.60(13) . . . . ?
O6 C3A C10C C10B 76.08(13) . . . . ?
C3 C3A C10C C10B -44.41(15) . . . . ?
C4 C3A C10C C10B -178.86(11) . . . . ?
O6 C3A C10C C6A -32.87(13) . . . . ?
C3 C3A C10C C6A -153.35(11) . . . . ?
C4 C3A C10C C6A 72.20(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350093
