#------------------------------------------------------------------------------
#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/79/4117923.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_4117923
loop_
_publ_author_name
'Ken Yamashita'
'Yoshihiko Yamamoto'
'Hisao Nishiyama'
_publ_section_title
;
 Ruthenium-Catalyzed Transfer Oxygenative Cyclization of α,ω-Diynes:
 Unprecedented [2 + 2 + 1] Route to Bicyclic Furans via
 Ruthenacyclopentatriene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7660
_journal_page_last               7663
_journal_paper_doi               10.1021/ja302868s
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C36 H28 O6 S2'
_chemical_formula_weight         620.70
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.0720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.6727(18)
_cell_length_b                   7.9317(6)
_cell_length_c                   18.6280(16)
_cell_measurement_reflns_used    5760
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     2900.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20913
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.04
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.772084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'empirical (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      0
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         7198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                5488
_reflns_number_total             7198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302868s_si_001.cif
_cod_data_source_block           ky221
_cod_database_code               4117923
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.05949(8) 0.0483(2) 0.88399(10) 0.0173(3) Uani 1 1 d .
C2 C 0.12346(9) 0.0318(2) 0.88417(10) 0.0215(4) Uani 1 1 d .
H2 H 0.1620 0.0821 0.9254 0.026 Uiso 1 1 calc R
C3 C 0.13145(10) -0.0570(2) 0.82494(11) 0.0261(4) Uani 1 1 d .
H3 H 0.1753 -0.0669 0.8254 0.031 Uiso 1 1 calc R
C4 C 0.07561(10) -0.1319(2) 0.76463(11) 0.0259(4) Uani 1 1 d .
H4 H 0.0812 -0.1951 0.7245 0.031 Uiso 1 1 calc R
C5 C 0.01172(10) -0.1137(2) 0.76350(10) 0.0229(4) Uani 1 1 d .
H5 H -0.0266 -0.1638 0.7220 0.028 Uiso 1 1 calc R
C6 C 0.00302(9) -0.0236(2) 0.82194(10) 0.0186(3) Uani 1 1 d .
H6 H -0.0412 -0.0105 0.8201 0.022 Uiso 1 1 calc R
C7 C 0.05223(8) 0.1374(2) 0.94803(10) 0.0162(3) Uani 1 1 d .
C8 C 0.09641(8) 0.1895(2) 1.02134(10) 0.0166(3) Uani 1 1 d .
C9 C 0.17115(8) 0.1787(2) 1.07160(10) 0.0196(4) Uani 1 1 d .
H9A H 0.1962 0.2679 1.0578 0.024 Uiso 1 1 calc R
H9B H 0.1895 0.0671 1.0667 0.024 Uiso 1 1 calc R
C10 C 0.09777(8) 0.3308(2) 1.13959(10) 0.0185(3) Uani 1 1 d .
H10A H 0.0743 0.3070 1.1739 0.022 Uiso 1 1 calc R
H10B H 0.1067 0.4533 1.1403 0.022 Uiso 1 1 calc R
C11 C 0.05750(8) 0.2684(2) 1.05719(10) 0.0168(3) Uani 1 1 d .
C12 C -0.00894(9) 0.2607(2) 1.00446(10) 0.0169(3) Uani 1 1 d .
C13 C -0.07316(8) 0.3130(2) 1.00454(10) 0.0177(3) Uani 1 1 d .
C14 C -0.07421(9) 0.4034(2) 1.06826(11) 0.0222(4) Uani 1 1 d .
H14 H -0.0326 0.4348 1.1111 0.027 Uiso 1 1 calc R
C15 C -0.13546(9) 0.4478(2) 1.06957(11) 0.0265(4) Uani 1 1 d .
H15 H -0.1357 0.5079 1.1136 0.032 Uiso 1 1 calc R
C16 C -0.19651(10) 0.4047(2) 1.00695(12) 0.0289(4) Uani 1 1 d .
H16 H -0.2385 0.4353 1.0080 0.035 Uiso 1 1 calc R
C17 C -0.19612(9) 0.3174(2) 0.94305(11) 0.0266(4) Uani 1 1 d .
H17 H -0.2380 0.2891 0.8998 0.032 Uiso 1 1 calc R
C18 C -0.13503(9) 0.2705(2) 0.94152(11) 0.0216(4) Uani 1 1 d .
H18 H -0.1352 0.2093 0.8976 0.026 Uiso 1 1 calc R
O1 O -0.01268(6) 0.18133(14) 0.93688(7) 0.0172(3) Uani 1 1 d .
O2 O 0.16545(6) 0.05029(16) 1.19982(7) 0.0270(3) Uani 1 1 d .
O3 O 0.23381(6) 0.30830(17) 1.21834(8) 0.0307(3) Uani 1 1 d .
S1 S 0.33848(2) 0.20748(6) 0.99945(3) 0.02114(11) Uani 1 1 d .
C19 C 0.44448(9) 0.4390(2) 0.82766(10) 0.0176(3) Uani 1 1 d .
C20 C 0.38031(9) 0.4409(2) 0.76357(10) 0.0218(4) Uani 1 1 d .
H20 H 0.3440 0.3777 0.7659 0.026 Uiso 1 1 calc R
C21 C 0.36960(10) 0.5346(2) 0.69669(11) 0.0263(4) Uani 1 1 d .
H21 H 0.3259 0.5351 0.6533 0.032 Uiso 1 1 calc R
C22 C 0.42190(10) 0.6274(2) 0.69253(11) 0.0273(4) Uani 1 1 d .
H22 H 0.4138 0.6944 0.6471 0.033 Uiso 1 1 calc R
C23 C 0.48648(10) 0.6223(2) 0.75507(11) 0.0258(4) Uani 1 1 d .
H23 H 0.5228 0.6832 0.7516 0.031 Uiso 1 1 calc R
C24 C 0.49804(9) 0.5292(2) 0.82228(10) 0.0206(4) Uani 1 1 d .
H24 H 0.5422 0.5262 0.8648 0.025 Uiso 1 1 calc R
C25 C 0.45555(8) 0.3465(2) 0.89947(10) 0.0174(3) Uani 1 1 d .
C26 C 0.41501(8) 0.2691(2) 0.92883(10) 0.0166(3) Uani 1 1 d .
C27 C 0.34053(8) 0.2454(2) 0.90458(10) 0.0192(4) Uani 1 1 d .
H27A H 0.3226 0.1478 0.8686 0.023 Uiso 1 1 calc R
H27B H 0.3144 0.3477 0.8786 0.023 Uiso 1 1 calc R
C28 C 0.42319(8) 0.1223(2) 1.04888(10) 0.0180(3) Uani 1 1 d .
H28A H 0.4444 0.1529 1.1058 0.022 Uiso 1 1 calc R
H28B H 0.4232 -0.0019 1.0436 0.022 Uiso 1 1 calc R
C29 C 0.45856(8) 0.2053(2) 1.00511(10) 0.0168(3) Uani 1 1 d .
C30 C 0.52372(8) 0.2462(2) 1.01931(10) 0.0170(3) Uani 1 1 d .
C31 C 0.59007(8) 0.2232(2) 1.08525(10) 0.0179(3) Uani 1 1 d .
C32 C 0.59671(9) 0.1276(2) 1.15135(10) 0.0211(4) Uani 1 1 d .
H32 H 0.5579 0.0736 1.1523 0.025 Uiso 1 1 calc R
C33 C 0.65954(9) 0.1115(2) 1.21526(11) 0.0241(4) Uani 1 1 d .
H33 H 0.6637 0.0471 1.2601 0.029 Uiso 1 1 calc R
C34 C 0.71640(9) 0.1890(2) 1.21414(11) 0.0261(4) Uani 1 1 d .
H34 H 0.7594 0.1781 1.2582 0.031 Uiso 1 1 calc R
C35 C 0.71049(9) 0.2822(2) 1.14885(11) 0.0256(4) Uani 1 1 d .
H35 H 0.7496 0.3353 1.1482 0.031 Uiso 1 1 calc R
C36 C 0.64799(9) 0.2986(2) 1.08433(11) 0.0214(4) Uani 1 1 d .
H36 H 0.6445 0.3614 1.0393 0.026 Uiso 1 1 calc R
O4 O 0.52249(6) 0.33137(14) 0.95445(7) 0.0173(2) Uani 1 1 d .
O5 O 0.33756(6) 0.36776(17) 1.03501(7) 0.0280(3) Uani 1 1 d .
O6 O 0.28771(6) 0.08521(18) 0.99326(8) 0.0337(3) Uani 1 1 d .
S2 S 0.17543(2) 0.21009(5) 1.16975(3) 0.02063(11) Uani 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'
S S 0.1246 0.1234 '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
C2 C1 C6 119.04(16)
C2 C1 C7 119.92(15)
C6 C1 C7 121.04(15)
C3 C2 C1 120.56(17)
C2 C3 C4 120.23(17)
C5 C4 C3 119.43(17)
C6 C5 C4 120.83(17)
C5 C6 C1 119.88(16)
C8 C7 O1 108.33(14)
C8 C7 C1 134.35(15)
O1 C7 C1 117.32(14)
C7 C8 C11 107.47(14)
C7 C8 C9 136.83(16)
C11 C8 C9 115.64(15)
C8 C9 S2 101.74(12)
C11 C10 S2 101.88(11)
C12 C11 C8 107.35(15)
C12 C11 C10 137.55(16)
C8 C11 C10 115.07(14)
C11 C12 O1 108.38(14)
C11 C12 C13 135.15(16)
O1 C12 C13 116.46(14)
C14 C13 C18 118.86(16)
C14 C13 C12 120.58(16)
C18 C13 C12 120.54(16)
C15 C14 C13 120.49(17)
C14 C15 C16 120.26(18)
C17 C16 C15 119.80(17)
C16 C17 C18 120.46(18)
C17 C18 C13 120.13(17)
C7 O1 C12 108.46(12)
O6 S1 O5 118.36(9)
O6 S1 C28 111.63(8)
O5 S1 C28 107.84(8)
O6 S1 C27 111.66(8)
O5 S1 C27 108.26(8)
C28 S1 C27 96.90(8)
C20 C19 C24 119.18(16)
C20 C19 C25 120.54(16)
C24 C19 C25 120.28(15)
C21 C20 C19 120.12(17)
C22 C21 C20 120.56(18)
C21 C22 C23 119.73(17)
C24 C23 C22 120.39(18)
C23 C24 C19 119.97(17)
C26 C25 O4 108.45(14)
C26 C25 C19 135.55(16)
O4 C25 C19 115.98(14)
C25 C26 C29 107.06(15)
C25 C26 C27 137.25(16)
C29 C26 C27 115.56(15)
C26 C27 S1 101.32(11)
C29 C28 S1 101.77(11)
C30 C29 C26 107.66(15)
C30 C29 C28 137.02(16)
C26 C29 C28 115.24(14)
C29 C30 O4 108.31(14)
C29 C30 C31 135.05(16)
O4 C30 C31 116.62(14)
C36 C31 C32 118.98(16)
C36 C31 C30 120.54(16)
C32 C31 C30 120.48(16)
C33 C32 C31 120.23(17)
C32 C33 C34 120.25(17)
C35 C34 C33 119.96(17)
C34 C35 C36 120.39(18)
C35 C36 C31 120.18(17)
C30 O4 C25 108.51(13)
O3 S2 O2 118.09(8)
O3 S2 C10 111.41(8)
O2 S2 C10 108.30(8)
O3 S2 C9 111.49(8)
O2 S2 C9 108.69(8)
C10 S2 C9 96.70(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.391(2)
C1 C6 1.400(2)
C1 C7 1.451(2)
C2 C3 1.380(2)
C3 C4 1.388(3)
C4 C5 1.383(3)
C5 C6 1.380(2)
C7 C8 1.358(2)
C7 O1 1.3771(19)
C8 C11 1.423(2)
C8 C9 1.491(2)
C9 S2 1.8083(18)
C10 C11 1.492(2)
C10 S2 1.8065(17)
C11 C12 1.358(2)
C12 O1 1.379(2)
C12 C13 1.453(2)
C13 C14 1.395(2)
C13 C18 1.399(2)
C14 C15 1.383(2)
C15 C16 1.385(3)
C16 C17 1.381(3)
C17 C18 1.387(2)
O2 S2 1.4386(13)
O3 S2 1.4340(13)
S1 O6 1.4343(14)
S1 O5 1.4376(13)
S1 C28 1.8006(17)
S1 C27 1.8117(18)
C19 C20 1.397(2)
C19 C24 1.403(2)
C19 C25 1.453(2)
C20 C21 1.383(3)
C21 C22 1.381(3)
C22 C23 1.391(3)
C23 C24 1.382(2)
C25 C26 1.362(2)
C25 O4 1.3816(19)
C26 C29 1.425(2)
C26 C27 1.492(2)
C28 C29 1.489(2)
C29 C30 1.361(2)
C30 O4 1.375(2)
C30 C31 1.454(2)
C31 C36 1.397(2)
C31 C32 1.400(2)
C32 C33 1.383(2)
C33 C34 1.385(3)
C34 C35 1.382(3)
C35 C36 1.384(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660625
2 PubChem 139121113
