#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028035.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_4028035
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         'C30 H18 O6'
_chemical_formula_sum            'C30 H18 O6'
_chemical_formula_weight         474.44
_chemical_name_systematic
;
 hexa(furan-2-yl)benzene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.22(3)
_cell_angle_beta                 100.96(3)
_cell_angle_gamma                104.09(4)
_cell_formula_units_Z            1
_cell_length_a                   5.765(3)
_cell_length_b                   9.629(4)
_cell_length_c                   11.290(6)
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    93.1500
_cell_measurement_theta_max      27.4083
_cell_measurement_theta_min      3.6071
_cell_volume                     552.8(5)
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8683
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       Block
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.2400
_exptl_crystal_size_mid          0.1800
_exptl_crystal_size_min          0.0800
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0388
_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)+(0.0661P)²+0.0859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                2091
_reflns_number_total             2499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302652r_si_002_3.cif
_cod_data_source_block           2a
_cod_original_cell_volume        552.8(4)
_cod_database_code               4028035
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 0.1325(2) 0.91478(14) 0.54796(11) 0.0139(3) Uani 1 1 d .
C2 C 0.0325(2) 0.86965(14) 0.41243(11) 0.0144(3) Uani 1 1 d .
C3 C -0.1004(2) 0.95564(14) 0.36396(11) 0.0145(3) Uani 1 1 d .
O1 O 0.51702(17) 0.86642(11) 0.62558(9) 0.0212(2) Uani 1 1 d .
O2 O -0.14229(16) 0.62838(10) 0.22469(8) 0.0190(2) Uani 1 1 d .
O3 O -0.02906(16) 0.88645(10) 0.15163(8) 0.0178(2) Uani 1 1 d .
C4 C 0.2620(2) 0.81858(14) 0.59637(11) 0.0146(3) Uani 1 1 d .
C5 C 0.1768(3) 0.68333(15) 0.61161(12) 0.0192(3) Uani 1 1 d .
H5 H 0.0078 0.6263 0.5976 0.023 Uiso 1 1 calc R
C6 C 0.3963(3) 0.64314(16) 0.65364(13) 0.0246(3) Uani 1 1 d .
H6 H 0.3999 0.5542 0.6727 0.030 Uiso 1 1 calc R
C7 C 0.5926(3) 0.75607(17) 0.66024(13) 0.0248(3) Uani 1 1 d .
H7 H 0.7615 0.7596 0.6855 0.030 Uiso 1 1 calc R
C8 C 0.0680(2) 0.73259(14) 0.32303(11) 0.0153(3) Uani 1 1 d .
C9 C 0.2700(2) 0.68742(16) 0.31035(12) 0.0194(3) Uani 1 1 d .
H9 H 0.4362 0.7383 0.3660 0.023 Uiso 1 1 calc R
C10 C 0.1842(3) 0.54818(16) 0.19682(13) 0.0227(3) Uani 1 1 d .
H10 H 0.2823 0.4889 0.1619 0.027 Uiso 1 1 calc R
C11 C -0.0628(3) 0.51771(16) 0.14927(13) 0.0225(3) Uani 1 1 d .
H11 H -0.1681 0.4313 0.0737 0.027 Uiso 1 1 calc R
C12 C -0.1952(2) 0.91514(14) 0.22220(11) 0.0153(3) Uani 1 1 d .
C13 C -0.4177(2) 0.89453(15) 0.14142(12) 0.0191(3) Uani 1 1 d .
H13 H -0.5625 0.9075 0.1656 0.023 Uiso 1 1 calc R
C14 C -0.3917(3) 0.84915(15) 0.01214(12) 0.0202(3) Uani 1 1 d .
H14 H -0.5159 0.8261 -0.0662 0.024 Uiso 1 1 calc R
C15 C -0.1567(3) 0.84569(15) 0.02366(12) 0.0198(3) Uani 1 1 d .
H15 H -0.0884 0.8187 -0.0472 0.024 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
C3 C1 C2 120.68(11) 2_576
C3 C1 C4 120.57(11) 2_576
C2 C1 C4 118.68(11) .
C1 C2 C3 119.82(11) .
C1 C2 C8 119.23(11) .
C3 C2 C8 120.95(11) .
C1 C3 C2 119.50(11) 2_576
C1 C3 C12 119.80(11) 2_576
C2 C3 C12 120.64(11) .
C4 O1 C7 106.29(11) .
C11 O2 C8 105.88(11) .
C15 O3 C12 106.10(10) .
C5 C4 O1 110.62(12) .
C5 C4 C1 132.52(12) .
O1 C4 C1 116.74(11) .
C4 C5 C6 105.88(13) .
C4 C5 H5 127.1 .
C6 C5 H5 127.1 .
C7 C6 C5 106.37(13) .
C7 C6 H6 126.8 .
C5 C6 H6 126.8 .
C6 C7 O1 110.85(12) .
C6 C7 H7 124.6 .
O1 C7 H7 124.6 .
C9 C8 O2 110.10(11) .
C9 C8 C2 133.82(12) .
O2 C8 C2 115.96(11) .
C8 C9 C10 106.60(13) .
C8 C9 H9 126.7 .
C10 C9 H9 126.7 .
C11 C10 C9 106.49(13) .
C11 C10 H10 126.8 .
C9 C10 H10 126.8 .
C10 C11 O2 110.92(12) .
C10 C11 H11 124.5 .
O2 C11 H11 124.5 .
C13 C12 O3 110.11(11) .
C13 C12 C3 134.14(12) .
O3 C12 C3 115.72(11) .
C12 C13 C14 106.47(12) .
C12 C13 H13 126.8 .
C14 C13 H13 126.8 .
C15 C14 C13 106.48(12) .
C15 C14 H14 126.8 .
C13 C14 H14 126.8 .
C14 C15 O3 110.84(12) .
C14 C15 H15 124.6 .
O3 C15 H15 124.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.4095(18) 2_576
C1 C2 1.4104(18) .
C1 C4 1.4872(17) .
C2 C3 1.4157(18) .
C2 C8 1.4763(18) .
C3 C1 1.4096(18) 2_576
C3 C12 1.4783(18) .
O1 C4 1.3690(17) .
O1 C7 1.3756(18) .
O2 C11 1.3747(17) .
O2 C8 1.3816(17) .
O3 C15 1.3723(16) .
O3 C12 1.3821(16) .
C4 C5 1.3518(19) .
C5 C6 1.449(2) .
C5 H5 0.9500 .
C6 C7 1.337(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.3555(19) .
C9 C10 1.431(2) .
C9 H9 0.9500 .
C10 C11 1.345(2) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.3545(19) .
C13 C14 1.4353(19) .
C13 H13 0.9500 .
C14 C15 1.346(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
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 0.37(19) 2_576 .
C4 C1 C2 C3 177.46(11) . .
C3 C1 C2 C8 -179.52(11) 2_576 .
C4 C1 C2 C8 -2.43(17) . .
C1 C2 C3 C1 -0.37(19) . 2_576
C8 C2 C3 C1 179.52(11) . 2_576
C1 C2 C3 C12 176.79(11) . .
C8 C2 C3 C12 -3.32(18) . .
C7 O1 C4 C5 0.03(13) . .
C7 O1 C4 C1 -176.47(10) . .
C3 C1 C4 C5 98.60(17) 2_576 .
C2 C1 C4 C5 -78.50(18) . .
C3 C1 C4 O1 -85.84(14) 2_576 .
C2 C1 C4 O1 97.07(14) . .
O1 C4 C5 C6 -0.06(14) . .
C1 C4 C5 C6 175.71(13) . .
C4 C5 C6 C7 0.07(14) . .
C5 C6 C7 O1 -0.05(15) . .
C4 O1 C7 C6 0.01(15) . .
C11 O2 C8 C9 -0.80(14) . .
C11 O2 C8 C2 175.86(10) . .
C1 C2 C8 C9 -51.3(2) . .
C3 C2 C8 C9 128.77(16) . .
C1 C2 C8 O2 133.01(12) . .
C3 C2 C8 O2 -46.88(16) . .
O2 C8 C9 C10 0.83(14) . .
C2 C8 C9 C10 -175.00(13) . .
C8 C9 C10 C11 -0.54(15) . .
C9 C10 C11 O2 0.05(16) . .
C8 O2 C11 C10 0.45(15) . .
C15 O3 C12 C13 -0.58(14) . .
C15 O3 C12 C3 177.68(10) . .
C1 C3 C12 C13 -50.7(2) 2_576 .
C2 C3 C12 C13 132.12(16) . .
C1 C3 C12 O3 131.55(12) 2_576 .
C2 C3 C12 O3 -45.60(16) . .
O3 C12 C13 C14 0.41(15) . .
C3 C12 C13 C14 -177.40(13) . .
C12 C13 C14 C15 -0.08(15) . .
C13 C14 C15 O3 -0.28(15) . .
C12 O3 C15 C14 0.53(14) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71614838
