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#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023580.cif $
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#
# 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_4023580
loop_
_publ_author_name
'Victorio Cadierno'
'Josefina Díez'
'José Gimeno'
'Noel Nebra'
_publ_contact_author
;     Josefina Díez
      Departamento de Química Orgánica e Inorgánica
      Facultad de Química
      Universidad de Oviedo
      Avda. Julián Clavería, 8
      33071 Oviedo
      Spain
;
_publ_contact_author_email       jdv@uniovi.es
_publ_contact_author_fax         '0034 98 5103446'
_publ_contact_author_phone       '0034 98 5102960'
_publ_section_title
;
 Ruthenium/TFA-Catalyzed Coupling of Activated Secondary Propargylic
 Alcohols with Cyclic 1,3-Diones: Furan versus Pyran Ring Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5852
_journal_page_last               5858
_journal_paper_doi               10.1021/jo800726u
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C12 H10 O2 S'
_chemical_formula_sum            'C12 H10 O2 S'
_chemical_formula_weight         218.26
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 100.571(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9439(4)
_cell_length_b                   6.1791(3)
_cell_length_c                   17.0548(7)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.407
_cell_volume                     1030.14(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowki & Minor 1997)'
_computing_data_collection       'Collet (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2007)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 92 (Altomare A., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95 mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12603
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.035
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0538
_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)+(0.1308P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                1267
_reflns_number_total             1849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800726u-File001_2.cif
_cod_data_source_block           13j
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023580
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9063(4) -0.0959(8) 0.3427(2) 0.0721(11) Uani 1 1 d . . .
C2 C 0.9107(4) -0.2953(8) 0.3137(2) 0.0741(11) Uani 1 1 d . . .
C3 C 0.8157(3) -0.3307(7) 0.2421(2) 0.0588(9) Uani 1 1 d . . .
C4 C 0.7406(3) -0.1515(5) 0.21823(16) 0.0444(7) Uani 1 1 d . . .
C5 C 0.6325(3) -0.1190(5) 0.14362(17) 0.0446(7) Uani 1 1 d . . .
C6 C 0.5079(3) -0.0026(6) 0.16034(19) 0.0545(8) Uani 1 1 d . . .
C7 C 0.4672(3) 0.1866(6) 0.1310(2) 0.0586(9) Uani 1 1 d . . .
C8 C 0.6366(3) 0.2021(4) 0.05492(17) 0.0463(7) Uani 1 1 d . . .
C9 C 0.6858(2) 0.0088(4) 0.08143(15) 0.0403(6) Uani 1 1 d . . .
C10 C 0.7073(3) 0.3070(5) -0.0049(2) 0.0542(8) Uani 1 1 d . . .
C11 C 0.8146(3) 0.1392(6) -0.01587(19) 0.0516(7) Uani 1 1 d . . .
C12 C 0.7956(2) -0.0475(4) 0.03927(16) 0.0421(7) Uani 1 1 d . . .
O1 O 0.5297(2) 0.3036(3) 0.07751(13) 0.0593(6) Uani 1 1 d . . .
O2 O 0.86171(19) -0.2156(3) 0.04612(14) 0.0593(6) Uani 1 1 d . . .
S1 S 0.78642(9) 0.05792(14) 0.28375(5) 0.0642(4) Uani 1 1 d . . .
H1 H 0.950(4) -0.047(6) 0.397(2) 0.076(11) Uiso 1 1 d . . .
H2 H 0.970(4) -0.404(7) 0.335(2) 0.082(12) Uiso 1 1 d . . .
H3 H 0.800(2) -0.437(4) 0.2184(14) 0.017(6) Uiso 1 1 d . . .
H5 H 0.612(3) -0.244(5) 0.1262(16) 0.045(8) Uiso 1 1 d . . .
H6 H 0.459(3) -0.060(5) 0.1938(18) 0.053(9) Uiso 1 1 d . . .
H7 H 0.391(4) 0.254(6) 0.141(2) 0.081(12) Uiso 1 1 d . . .
H10A H 0.646(4) 0.334(6) -0.054(2) 0.073(10) Uiso 1 1 d . . .
H10B H 0.748(4) 0.438(6) 0.012(2) 0.076(11) Uiso 1 1 d . . .
H11A H 0.806(3) 0.086(4) -0.0703(18) 0.046(8) Uiso 1 1 d . . .
H11B H 0.916(3) 0.187(5) -0.0045(19) 0.060(9) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 111.4(3) . . ?
C2 C1 H1 126(2) . . ?
S1 C1 H1 121(2) . . ?
C1 C2 C3 113.6(3) . . ?
C1 C2 H2 127(2) . . ?
C3 C2 H2 120(2) . . ?
C4 C3 C2 112.1(4) . . ?
C4 C3 H3 119.6(19) . . ?
C2 C3 H3 128.3(19) . . ?
C3 C4 C5 128.6(3) . . ?
C3 C4 S1 110.8(2) . . ?
C5 C4 S1 120.5(2) . . ?
C9 C5 C6 107.1(2) . . ?
C9 C5 C4 112.0(2) . . ?
C6 C5 C4 112.6(3) . . ?
C9 C5 H5 109.3(19) . . ?
C6 C5 H5 110.3(19) . . ?
C4 C5 H5 105.5(19) . . ?
C7 C6 C5 124.3(3) . . ?
C7 C6 H6 116(2) . . ?
C5 C6 H6 120(2) . . ?
C6 C7 O1 124.8(3) . . ?
C6 C7 H7 123(2) . . ?
O1 C7 H7 112(2) . . ?
C9 C8 O1 125.2(3) . . ?
C9 C8 C10 115.5(3) . . ?
O1 C8 C10 119.2(2) . . ?
C8 C9 C12 107.9(3) . . ?
C8 C9 C5 123.8(3) . . ?
C12 C9 C5 128.3(2) . . ?
C8 C10 C11 102.5(2) . . ?
C8 C10 H10A 111(2) . . ?
C11 C10 H10A 111(2) . . ?
C8 C10 H10B 113(3) . . ?
C11 C10 H10B 111(2) . . ?
H10A C10 H10B 107(3) . . ?
C12 C11 C10 105.7(2) . . ?
C12 C11 H11A 109.5(17) . . ?
C10 C11 H11A 114.2(16) . . ?
C12 C11 H11B 109.2(17) . . ?
C10 C11 H11B 117.5(18) . . ?
H11A C11 H11B 101(2) . . ?
O2 C12 C9 126.5(3) . . ?
O2 C12 C11 125.3(3) . . ?
C9 C12 C11 108.2(2) . . ?
C8 O1 C7 114.5(2) . . ?
C1 S1 C4 92.11(19) . . ?
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 C2 1.331(6) . ?
C1 S1 1.701(4) . ?
C1 H1 0.99(3) . ?
C2 C3 1.418(5) . ?
C2 H2 0.92(4) . ?
C3 C4 1.355(4) . ?
C3 H3 0.77(2) . ?
C4 C5 1.521(4) . ?
C4 S1 1.716(3) . ?
C5 C9 1.495(4) . ?
C5 C6 1.505(4) . ?
C5 H5 0.84(3) . ?
C6 C7 1.306(5) . ?
C6 H6 0.88(3) . ?
C7 O1 1.396(4) . ?
C7 H7 0.91(4) . ?
C8 C9 1.338(4) . ?
C8 O1 1.350(3) . ?
C8 C10 1.490(4) . ?
C9 C12 1.456(4) . ?
C10 C11 1.523(5) . ?
C10 H10A 0.96(4) . ?
C10 H10B 0.93(4) . ?
C11 C12 1.522(4) . ?
C11 H11A 0.98(3) . ?
C11 H11B 1.04(3) . ?
C12 O2 1.223(3) . ?
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
S1 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 177.5(3) . . . . ?
C2 C3 C4 S1 -0.3(4) . . . . ?
C3 C4 C5 C9 -103.0(4) . . . . ?
S1 C4 C5 C9 74.5(3) . . . . ?
C3 C4 C5 C6 136.2(3) . . . . ?
S1 C4 C5 C6 -46.2(3) . . . . ?
C9 C5 C6 C7 -6.8(4) . . . . ?
C4 C5 C6 C7 116.8(3) . . . . ?
C5 C6 C7 O1 2.8(5) . . . . ?
O1 C8 C9 C12 176.9(2) . . . . ?
C10 C8 C9 C12 -2.4(3) . . . . ?
O1 C8 C9 C5 -3.0(4) . . . . ?
C10 C8 C9 C5 177.7(3) . . . . ?
C6 C5 C9 C8 6.9(4) . . . . ?
C4 C5 C9 C8 -117.1(3) . . . . ?
C6 C5 C9 C12 -173.0(3) . . . . ?
C4 C5 C9 C12 63.0(4) . . . . ?
C9 C8 C10 C11 1.6(4) . . . . ?
O1 C8 C10 C11 -177.7(3) . . . . ?
C8 C10 C11 C12 -0.2(3) . . . . ?
C8 C9 C12 O2 -177.6(3) . . . . ?
C5 C9 C12 O2 2.3(4) . . . . ?
C8 C9 C12 C11 2.1(3) . . . . ?
C5 C9 C12 C11 -178.0(3) . . . . ?
C10 C11 C12 O2 178.6(3) . . . . ?
C10 C11 C12 C9 -1.1(3) . . . . ?
C9 C8 O1 C7 -2.1(4) . . . . ?
C10 C8 O1 C7 177.2(3) . . . . ?
C6 C7 O1 C8 2.2(5) . . . . ?
C2 C1 S1 C4 0.0(3) . . . . ?
C3 C4 S1 C1 0.1(3) . . . . ?
C5 C4 S1 C1 -177.8(2) . . . . ?
