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#$Date: 2020-10-04 05:45:43 +0300 (Sun, 04 Oct 2020) $
#$Revision: 256997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/80/4518065.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_4518065
loop_
_publ_author_name
'Karlinskii, Bogdan Ya.'
'Kostyukovich, Alexander Yu.'
'Kucherov, Fedor A.'
'Galkin, Konstantin I.'
'Kozlov, Kirill S.'
'Ananikov, Valentine P.'
_publ_section_title
;
 Directing-Group-Free, Carbonyl Group-Promoted Catalytic C--H Arylation of
 Bio-Based Furans
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              11466
_journal_page_last               11480
_journal_paper_doi               10.1021/acscatal.0c02143
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H12 O3'
_chemical_formula_sum            'C18 H12 O3'
_chemical_formula_weight         276.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.3160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3333(4)
_cell_length_b                   11.1772(4)
_cell_length_c                   19.7023(6)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.07
_cell_measurement_theta_min      2.48
_cell_volume                     2663.20(15)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_publication_material
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'ω shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.000
_diffrn_reflns_theta_min         2.481
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.7191
_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    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0577P)²+1.7684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3908
_reflns_number_total             5431
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c02143_si_003.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 4518064--4518066.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4518065
_shelx_shelxl_version_number     2018/3
_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   0.963
_shelx_estimated_absorpt_t_max   0.986
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'
'-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
O1 O 0.80031(8) 0.38932(8) 0.45538(5) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.75997(10) 0.40567(10) 0.50612(6) 0.0212(2) Uani 1 1 d . . . . .
H1 H 0.7693(12) 0.3482(14) 0.5454(8) 0.020(4) Uiso 1 1 d . . . . .
C2 C 0.69422(9) 0.51042(9) 0.51572(6) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.64974(9) 0.54725(9) 0.57093(6) 0.01681(19) Uani 1 1 d . . . . .
C4 C 0.60410(9) 0.66362(9) 0.55259(6) 0.0169(2) Uani 1 1 d . . . . .
C5 C 0.62426(9) 0.68711(9) 0.48778(6) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.67945(7) 0.59472(7) 0.46444(4) 0.01826(16) Uani 1 1 d . . . . .
C6 C 0.59410(10) 0.78949(10) 0.44246(6) 0.0190(2) Uani 1 1 d . . . . .
H6 H 0.5450(13) 0.8473(14) 0.4599(8) 0.023(4) Uiso 1 1 d . . . . .
O3 O 0.62531(8) 0.80486(8) 0.38850(4) 0.02284(18) Uani 1 1 d . . . . .
C7 C 0.65443(9) 0.48630(10) 0.63768(6) 0.0180(2) Uani 1 1 d . . . . .
C8 C 0.62637(10) 0.36609(10) 0.64073(7) 0.0226(2) Uani 1 1 d . . . . .
H8 H 0.6039(14) 0.3210(15) 0.5972(9) 0.029(4) Uiso 1 1 d . . . . .
C9 C 0.63051(11) 0.31130(12) 0.70461(8) 0.0279(3) Uani 1 1 d . . . . .
H9 H 0.6110(14) 0.2270(16) 0.7055(9) 0.034(4) Uiso 1 1 d . . . . .
C10 C 0.66399(11) 0.37481(13) 0.76516(7) 0.0286(3) Uani 1 1 d . . . . .
H10 H 0.6679(14) 0.3367(15) 0.8102(9) 0.030(4) Uiso 1 1 d . . . . .
C11 C 0.69354(11) 0.49455(12) 0.76238(7) 0.0254(2) Uani 1 1 d . . . . .
H11 H 0.7213(14) 0.5376(16) 0.8056(9) 0.034(4) Uiso 1 1 d . . . . .
C12 C 0.68796(10) 0.55051(10) 0.69905(6) 0.0204(2) Uani 1 1 d . . . . .
H12 H 0.7075(14) 0.6355(15) 0.6954(8) 0.028(4) Uiso 1 1 d . . . . .
C13 C 0.54751(9) 0.74356(10) 0.59366(6) 0.0177(2) Uani 1 1 d . . . . .
C14 C 0.46555(10) 0.69915(11) 0.62688(6) 0.0228(2) Uani 1 1 d . . . . .
H14 H 0.4458(14) 0.6128(15) 0.6230(8) 0.029(4) Uiso 1 1 d . . . . .
C15 C 0.41176(11) 0.77604(14) 0.66448(7) 0.0286(3) Uani 1 1 d . . . . .
H15 H 0.3546(15) 0.7452(16) 0.6874(9) 0.036(5) Uiso 1 1 d . . . . .
C16 C 0.43812(11) 0.89664(13) 0.66909(7) 0.0287(3) Uani 1 1 d . . . . .
H16 H 0.4002(14) 0.9505(16) 0.6946(9) 0.032(4) Uiso 1 1 d . . . . .
C17 C 0.52012(11) 0.94067(11) 0.63728(6) 0.0252(2) Uani 1 1 d . . . . .
H17 H 0.5405(14) 1.0251(15) 0.6416(9) 0.032(4) Uiso 1 1 d . . . . .
C18 C 0.57592(10) 0.86438(10) 0.60027(6) 0.0206(2) Uani 1 1 d . . . . .
H18 H 0.6351(13) 0.8954(14) 0.5791(8) 0.024(4) Uiso 1 1 d . . . . .
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
O1 C1 C2 123.77(11) . . ?
O1 C1 H1 122.7(8) . . ?
C2 C1 H1 113.5(8) . . ?
O2 C2 C3 111.26(9) . . ?
O2 C2 C1 117.02(10) . . ?
C3 C2 C1 131.47(11) . . ?
C2 C3 C4 105.67(9) . . ?
C2 C3 C7 128.08(10) . . ?
C4 C3 C7 126.09(10) . . ?
C5 C4 C3 105.89(9) . . ?
C5 C4 C13 125.99(10) . . ?
C3 C4 C13 128.12(10) . . ?
O2 C5 C4 111.21(9) . . ?
O2 C5 C6 118.21(9) . . ?
C4 C5 C6 130.56(10) . . ?
C5 O2 C2 105.97(8) . . ?
O3 C6 C5 124.28(11) . . ?
O3 C6 H6 122.1(9) . . ?
C5 C6 H6 113.6(9) . . ?
C8 C7 C12 119.50(11) . . ?
C8 C7 C3 121.26(11) . . ?
C12 C7 C3 119.24(10) . . ?
C9 C8 C7 119.91(12) . . ?
C9 C8 H8 121.1(10) . . ?
C7 C8 H8 119.0(10) . . ?
C10 C9 C8 120.48(12) . . ?
C10 C9 H9 121.0(10) . . ?
C8 C9 H9 118.5(10) . . ?
C9 C10 C11 119.81(12) . . ?
C9 C10 H10 121.0(10) . . ?
C11 C10 H10 119.2(10) . . ?
C12 C11 C10 120.19(12) . . ?
C12 C11 H11 120.6(10) . . ?
C10 C11 H11 119.2(10) . . ?
C11 C12 C7 120.10(11) . . ?
C11 C12 H12 122.0(10) . . ?
C7 C12 H12 117.9(10) . . ?
C18 C13 C14 119.43(11) . . ?
C18 C13 C4 120.14(10) . . ?
C14 C13 C4 120.43(10) . . ?
C15 C14 C13 119.72(12) . . ?
C15 C14 H14 120.4(10) . . ?
C13 C14 H14 119.8(9) . . ?
C16 C15 C14 120.51(12) . . ?
C16 C15 H15 119.8(11) . . ?
C14 C15 H15 119.7(11) . . ?
C17 C16 C15 120.03(12) . . ?
C17 C16 H16 119.2(10) . . ?
C15 C16 H16 120.8(10) . . ?
C16 C17 C18 120.13(12) . . ?
C16 C17 H17 120.3(10) . . ?
C18 C17 H17 119.5(10) . . ?
C17 C18 C13 120.14(12) . . ?
C17 C18 H18 119.8(9) . . ?
C13 C18 H18 120.0(9) . . ?
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
O1 C1 1.2145(15) . ?
C1 C2 1.4576(15) . ?
C1 H1 0.995(15) . ?
C2 O2 1.3674(13) . ?
C2 C3 1.3739(15) . ?
C3 C4 1.4351(15) . ?
C3 C7 1.4722(15) . ?
C4 C5 1.3732(15) . ?
C4 C13 1.4703(15) . ?
C5 O2 1.3654(13) . ?
C5 C6 1.4542(15) . ?
C6 O3 1.2118(14) . ?
C6 H6 0.992(15) . ?
C7 C8 1.3917(15) . ?
C7 C12 1.3970(17) . ?
C8 C9 1.3914(18) . ?
C8 H8 0.986(17) . ?
C9 C10 1.380(2) . ?
C9 H9 0.974(18) . ?
C10 C11 1.3910(19) . ?
C10 H10 0.978(17) . ?
C11 C12 1.3853(17) . ?
C11 H11 0.980(17) . ?
C12 H12 0.986(16) . ?
C13 C18 1.3948(16) . ?
C13 C14 1.3986(16) . ?
C14 C15 1.3858(18) . ?
C14 H14 0.994(17) . ?
C15 C16 1.385(2) . ?
C15 H15 0.972(17) . ?
C16 C17 1.381(2) . ?
C16 H16 0.962(17) . ?
C17 C18 1.3890(16) . ?
C17 H17 0.976(17) . ?
C18 H18 0.973(16) . ?
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
O1 C1 C2 O2 -0.91(17) . . . . ?
O1 C1 C2 C3 -174.64(12) . . . . ?
O2 C2 C3 C4 -0.19(12) . . . . ?
C1 C2 C3 C4 173.82(12) . . . . ?
O2 C2 C3 C7 -175.79(10) . . . . ?
C1 C2 C3 C7 -1.8(2) . . . . ?
C2 C3 C4 C5 0.31(12) . . . . ?
C7 C3 C4 C5 176.02(10) . . . . ?
C2 C3 C4 C13 -179.41(11) . . . . ?
C7 C3 C4 C13 -3.70(18) . . . . ?
C3 C4 C5 O2 -0.33(12) . . . . ?
C13 C4 C5 O2 179.40(10) . . . . ?
C3 C4 C5 C6 177.90(11) . . . . ?
C13 C4 C5 C6 -2.4(2) . . . . ?
C4 C5 O2 C2 0.22(12) . . . . ?
C6 C5 O2 C2 -178.26(10) . . . . ?
C3 C2 O2 C5 -0.01(12) . . . . ?
C1 C2 O2 C5 -174.97(10) . . . . ?
O2 C5 C6 O3 -8.75(17) . . . . ?
C4 C5 C6 O3 173.12(12) . . . . ?
C2 C3 C7 C8 -49.87(17) . . . . ?
C4 C3 C7 C8 135.38(12) . . . . ?
C2 C3 C7 C12 129.99(13) . . . . ?
C4 C3 C7 C12 -44.76(16) . . . . ?
C12 C7 C8 C9 0.82(17) . . . . ?
C3 C7 C8 C9 -179.32(11) . . . . ?
C7 C8 C9 C10 -1.04(19) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.90(19) . . . . ?
C10 C11 C12 C7 -1.11(18) . . . . ?
C8 C7 C12 C11 0.25(17) . . . . ?
C3 C7 C12 C11 -179.62(11) . . . . ?
C5 C4 C13 C18 -46.53(17) . . . . ?
C3 C4 C13 C18 133.14(12) . . . . ?
C5 C4 C13 C14 134.00(12) . . . . ?
C3 C4 C13 C14 -46.33(17) . . . . ?
C18 C13 C14 C15 1.56(17) . . . . ?
C4 C13 C14 C15 -178.97(11) . . . . ?
C13 C14 C15 C16 0.37(19) . . . . ?
C14 C15 C16 C17 -1.4(2) . . . . ?
C15 C16 C17 C18 0.39(19) . . . . ?
C16 C17 C18 C13 1.56(18) . . . . ?
C14 C13 C18 C17 -2.53(17) . . . . ?
C4 C13 C18 C17 178.00(11) . . . . ?
