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#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028036.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_4028036
loop_
_publ_author_name
'Koichi Mitsudo'
'Jyunji Harada'
'Yo Tanaka'
'Hiroki Mandai'
'Chie Nishioka'
'Hideo Tanaka'
'Atsushi Wakamiya'
'Yasujiro Murata'
'Seiji Suga'
_publ_contact_author_address
;
Graduate School of Natural Science and Technology, Okayama University,
3-1-1 Tsushima-naka, Okayama 700-8530, Japan
;
_publ_contact_author_email       suga@cc.okayama-u.ac.jp
_publ_contact_author_fax         +81-86-251-8081
_publ_contact_author_name        'Seiji Suga'
_publ_contact_author_phone       +81-86-251-8081
_publ_section_title
;
 Synthesis of Hexa(furan-2-yl)benzenes and Their π-Extended Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2763
_journal_page_last               2768
_journal_paper_doi               10.1021/jo302652r
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C36 H30 O6'
_chemical_formula_sum            'C36 H30 O6'
_chemical_formula_weight         558.60
_chemical_name_common            hexakis(5-methylfuran-2-yl)benzene
_chemical_name_systematic        hexakis(5-methylfuran-2-yl)benzene
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.048(10)
_cell_angle_beta                 101.158(7)
_cell_angle_gamma                97.855(8)
_cell_formula_units_Z            1
_cell_length_a                   7.657(4)
_cell_length_b                   8.565(5)
_cell_length_c                   11.673(7)
_cell_measurement_reflns_used    1998
_cell_measurement_temperature    93.1500
_cell_measurement_theta_max      27.5165
_cell_measurement_theta_min      3.2721
_cell_volume                     733.0(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11516
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.1600
_exptl_crystal_size_mid          0.1300
_exptl_crystal_size_min          0.0600
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0457
_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)+(0.0624P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                2411
_reflns_number_total             3346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302652r_si_002_4.cif
_cod_data_source_block           2b
_cod_database_code               4028036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.62733(18) -0.09852(15) 0.52977(12) 0.0202(3) Uani 1 1 d .
C2 C 0.52002(18) -0.12719(15) 0.41480(12) 0.0199(3) Uani 1 1 d .
C3 C 0.39165(18) -0.02737(15) 0.38479(12) 0.0206(3) Uani 1 1 d .
C4 C 0.74998(18) -0.21011(16) 0.56610(12) 0.0205(3) Uani 1 1 d .
C5 C 0.72439(18) -0.34976(16) 0.60602(12) 0.0224(3) Uani 1 1 d .
H5 H 0.6136 -0.4045 0.6166 0.027 Uiso 1 1 calc R
C6 C 0.89726(19) -0.39967(17) 0.62940(13) 0.0251(3) Uani 1 1 d .
H6 H 0.9229 -0.4939 0.6588 0.030 Uiso 1 1 calc R
C7 C 1.01634(19) -0.28804(16) 0.60182(13) 0.0237(3) Uani 1 1 d .
O1 O 0.92863(12) -0.16922(11) 0.56172(9) 0.0236(2) Uani 1 1 d .
C8 C 1.2129(2) -0.26614(19) 0.60603(15) 0.0323(4) Uani 1 1 d .
H8 H 1.2603 -0.3610 0.6281 0.048 Uiso 1 1 calc R
H8A H 1.2741 -0.1718 0.6649 0.048 Uiso 1 1 calc R
H8B H 1.2345 -0.2512 0.5279 0.048 Uiso 1 1 calc R
C9 C 0.54049(19) -0.26109(16) 0.32787(12) 0.0218(3) Uani 1 1 d .
C10 C 0.6858(2) -0.31617(17) 0.29700(13) 0.0281(3) Uani 1 1 d .
H10 H 0.8092 -0.2759 0.3323 0.034 Uiso 1 1 calc R
C11 C 0.6170(2) -0.44633(18) 0.20123(13) 0.0313(4) Uani 1 1 d .
H11 H 0.6862 -0.5088 0.1601 0.038 Uiso 1 1 calc R
C12 C 0.4351(2) -0.46415(17) 0.17999(13) 0.0280(3) Uani 1 1 d .
O2 O 0.38413(13) -0.35179(11) 0.25752(8) 0.0240(2) Uani 1 1 d .
C13 C 0.2853(2) -0.57780(19) 0.09727(14) 0.0394(4) Uani 1 1 d .
H13 H 0.3336 -0.6402 0.0373 0.059 Uiso 1 1 calc R
H13A H 0.1975 -0.5182 0.0583 0.059 Uiso 1 1 calc R
H13B H 0.2260 -0.6502 0.1415 0.059 Uiso 1 1 calc R
C14 C 0.27660(19) -0.05418(16) 0.26520(13) 0.0219(3) Uani 1 1 d .
C15 C 0.0953(2) -0.08016(17) 0.22520(14) 0.0280(3) Uani 1 1 d .
H15 H 0.0069 -0.0736 0.2719 0.034 Uiso 1 1 calc R
C16 C 0.0627(2) -0.11921(18) 0.09939(14) 0.0323(4) Uani 1 1 d .
H16 H -0.0521 -0.1450 0.0463 0.039 Uiso 1 1 calc R
C17 C 0.2241(2) -0.11287(17) 0.06955(14) 0.0294(4) Uani 1 1 d .
O3 O 0.36004(13) -0.07170(11) 0.17039(8) 0.0247(2) Uani 1 1 d .
C18 C 0.2810(2) -0.1355(2) -0.04536(14) 0.0416(4) Uani 1 1 d .
H18 H 0.1761 -0.1840 -0.1089 0.062 Uiso 1 1 calc R
H18A H 0.3721 -0.2058 -0.0418 0.062 Uiso 1 1 calc R
H18B H 0.3326 -0.0315 -0.0612 0.062 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
C2 C1 C3 120.85(13) . 2_656
C2 C1 C4 120.04(13) . .
C3 C1 C4 118.85(13) 2_656 .
C1 C2 C3 119.26(13) . .
C1 C2 C9 119.75(12) . .
C3 C2 C9 120.99(13) . .
C1 C3 C2 119.89(13) 2_656 .
C1 C3 C14 119.38(12) 2_656 .
C2 C3 C14 120.73(13) . .
C5 C4 O1 110.00(12) . .
C5 C4 C1 132.74(13) . .
O1 C4 C1 117.25(11) . .
C4 C5 C6 106.51(12) . .
C4 C5 H5 126.7 . .
C6 C5 H5 126.7 . .
C7 C6 C5 107.15(13) . .
C7 C6 H6 126.4 . .
C5 C6 H6 126.4 . .
C6 C7 O1 109.56(13) . .
C6 C7 C8 134.72(13) . .
O1 C7 C8 115.71(12) . .
C4 O1 C7 106.78(10) . .
C7 C8 H8 109.5 . .
C7 C8 H8A 109.5 . .
H8 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C10 C9 O2 109.65(13) . .
C10 C9 C2 133.46(14) . .
O2 C9 C2 116.85(12) . .
C9 C10 C11 106.58(14) . .
C9 C10 H10 126.7 . .
C11 C10 H10 126.7 . .
C12 C11 C10 107.18(13) . .
C12 C11 H11 126.4 . .
C10 C11 H11 126.4 . .
C11 C12 O2 109.66(13) . .
C11 C12 C13 134.62(15) . .
O2 C12 C13 115.68(14) . .
C12 O2 C9 106.91(12) . .
C12 C13 H13 109.5 . .
C12 C13 H13A 109.5 . .
H13 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C15 C14 O3 109.69(13) . .
C15 C14 C3 132.50(13) . .
O3 C14 C3 117.52(12) . .
C14 C15 C16 106.62(14) . .
C14 C15 H15 126.7 . .
C16 C15 H15 126.7 . .
C17 C16 C15 107.40(14) . .
C17 C16 H16 126.3 . .
C15 C16 H16 126.3 . .
C16 C17 O3 109.72(14) . .
C16 C17 C18 133.63(15) . .
O3 C17 C18 116.62(14) . .
C17 O3 C14 106.56(12) . .
C17 C18 H18 109.5 . .
C17 C18 H18A 109.5 . .
H18 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.401(2) .
C1 C3 1.406(2) 2_656
C1 C4 1.4764(19) .
C2 C3 1.4143(19) .
C2 C9 1.468(2) .
C3 C1 1.406(2) 2_656
C3 C14 1.469(2) .
C4 C5 1.3467(19) .
C4 O1 1.3775(17) .
C5 C6 1.434(2) .
C5 H5 0.9500 .
C6 C7 1.3456(19) .
C6 H6 0.9500 .
C7 O1 1.3799(16) .
C7 C8 1.481(2) .
C8 H8 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C9 C10 1.357(2) .
C9 O2 1.3776(17) .
C10 C11 1.426(2) .
C10 H10 0.9500 .
C11 C12 1.350(2) .
C11 H11 0.9500 .
C12 O2 1.3757(17) .
C12 C13 1.482(2) .
C13 H13 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 C15 1.353(2) .
C14 O3 1.3815(17) .
C15 C16 1.424(2) .
C15 H15 0.9500 .
C16 C17 1.344(2) .
C16 H16 0.9500 .
C17 O3 1.3795(18) .
C17 C18 1.484(2) .
C18 H18 0.9800 .
C18 H18A 0.9800 .
C18 H18B 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
C3 C1 C2 C3 0.2(2) 2_656 .
C4 C1 C2 C3 174.34(11) . .
C3 C1 C2 C9 -178.98(11) 2_656 .
C4 C1 C2 C9 -4.88(18) . .
C1 C2 C3 C1 -0.2(2) . 2_656
C9 C2 C3 C1 178.98(11) . 2_656
C1 C2 C3 C14 -179.85(12) . .
C9 C2 C3 C14 -0.65(18) . .
C2 C1 C4 C5 -83.1(2) . .
C3 C1 C4 C5 91.1(2) 2_656 .
C2 C1 C4 O1 97.85(15) . .
C3 C1 C4 O1 -87.93(15) 2_656 .
O1 C4 C5 C6 0.55(16) . .
C1 C4 C5 C6 -178.54(15) . .
C4 C5 C6 C7 -0.27(17) . .
C5 C6 C7 O1 -0.12(17) . .
C5 C6 C7 C8 179.37(16) . .
C5 C4 O1 C7 -0.63(15) . .
C1 C4 O1 C7 178.62(12) . .
C6 C7 O1 C4 0.45(16) . .
C8 C7 O1 C4 -179.14(12) . .
C1 C2 C9 C10 -44.9(2) . .
C3 C2 C9 C10 135.90(16) . .
C1 C2 C9 O2 137.44(13) . .
C3 C2 C9 O2 -41.76(17) . .
O2 C9 C10 C11 0.94(16) . .
C2 C9 C10 C11 -176.84(14) . .
C9 C10 C11 C12 -0.56(16) . .
C10 C11 C12 O2 -0.03(16) . .
C10 C11 C12 C13 -177.51(16) . .
C11 C12 O2 C9 0.60(15) . .
C13 C12 O2 C9 178.61(12) . .
C10 C9 O2 C12 -0.96(15) . .
C2 C9 O2 C12 177.24(11) . .
C1 C3 C14 C15 -56.0(2) 2_656 .
C2 C3 C14 C15 123.63(17) . .
C1 C3 C14 O3 130.85(13) 2_656 .
C2 C3 C14 O3 -49.53(17) . .
O3 C14 C15 C16 1.25(16) . .
C3 C14 C15 C16 -172.31(14) . .
C14 C15 C16 C17 -0.83(17) . .
C15 C16 C17 O3 0.10(17) . .
C15 C16 C17 C18 -177.69(17) . .
C16 C17 O3 C14 0.66(15) . .
C18 C17 O3 C14 178.86(12) . .
C15 C14 O3 C17 -1.20(15) . .
C3 C14 O3 C17 173.45(11) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71615041
