#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023373.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_4023373
loop_
_publ_author_name
'Guodong Yin'
'Zihua Wang'
'Aihua Chen'
'Meng Gao'
'Anxin Wu'
'Yuanjiang Pan'
_publ_section_title
;
 A New Facile Approach to the Synthesis of 3-Methylthio-Substituted
 Furans, Pyrroles, Thiophenes, and Related Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3377
_journal_page_last               3383
_journal_paper_doi               10.1021/jo702585s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C19 H18 O S'
_chemical_formula_sum            'C19 H18 O S'
_chemical_formula_weight         294.39
_chemical_name_systematic
; 
 ? 
;
_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                110.688(2)
_cell_angle_beta                 95.048(2)
_cell_angle_gamma                93.258(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6636(7)
_cell_length_b                   10.5669(13)
_cell_length_c                   14.0635(18)
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      3.06
_cell_volume                     780.83(17)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6762
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                2387
_reflns_number_total             3349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702585s-File002.cif
_cod_data_source_block           060901bm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4023373
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.85422(12) 0.33736(6) 0.46108(4) 0.0682(2) Uani 1 1 d . . .
O1 O 0.5595(2) 0.00802(12) 0.23791(9) 0.0459(3) Uani 1 1 d . . .
C1 C 1.2687(4) 0.2635(2) -0.00354(17) 0.0661(6) Uani 1 1 d . . .
H1A H 1.2339 0.3515 -0.0030 0.099 Uiso 1 1 calc R . .
H1B H 1.2266 0.1973 -0.0712 0.099 Uiso 1 1 calc R . .
H1C H 1.4356 0.2650 0.0165 0.099 Uiso 1 1 calc R . .
C2 C 1.1268(4) 0.2264(2) 0.07076(15) 0.0492(5) Uani 1 1 d . . .
C3 C 1.2143(4) 0.2603(2) 0.17193(15) 0.0507(5) Uani 1 1 d . . .
H3 H 1.3641 0.3076 0.1954 0.061 Uiso 1 1 calc R . .
C4 C 1.0848(4) 0.22561(19) 0.23953(14) 0.0475(5) Uani 1 1 d . . .
H4 H 1.1491 0.2490 0.3073 0.057 Uiso 1 1 calc R . .
C5 C 0.8591(3) 0.15605(18) 0.20706(13) 0.0416(4) Uani 1 1 d . . .
C6 C 0.7720(4) 0.12058(19) 0.10439(14) 0.0487(5) Uani 1 1 d . . .
H6 H 0.6226 0.0729 0.0805 0.058 Uiso 1 1 calc R . .
C7 C 0.9029(4) 0.1547(2) 0.03792(15) 0.0526(5) Uani 1 1 d . . .
H7 H 0.8408 0.1295 -0.0303 0.063 Uiso 1 1 calc R . .
C8 C 0.7165(3) 0.12398(18) 0.27833(14) 0.0432(4) Uani 1 1 d . . .
C9 C 0.6928(4) 0.18557(19) 0.37921(14) 0.0466(5) Uani 1 1 d . . .
C10 C 0.5144(4) 0.10501(19) 0.40249(14) 0.0493(5) Uani 1 1 d . . .
H10 H 0.4605 0.1219 0.4660 0.059 Uiso 1 1 calc R . .
C11 C 0.4371(4) -0.00088(19) 0.31536(14) 0.0453(5) Uani 1 1 d . . .
C12 C 0.6672(5) 0.3926(2) 0.56144(15) 0.0679(7) Uani 1 1 d . . .
H12A H 0.5074 0.3932 0.5325 0.102 Uiso 1 1 calc R . .
H12B H 0.7253 0.4826 0.6072 0.102 Uiso 1 1 calc R . .
H12C H 0.6684 0.3317 0.5984 0.102 Uiso 1 1 calc R . .
C13 C 0.2621(3) -0.11740(19) 0.29032(14) 0.0446(5) Uani 1 1 d . . .
C14 C 0.0715(4) -0.1120(2) 0.34671(16) 0.0540(5) Uani 1 1 d . . .
H14 H 0.0523 -0.0319 0.3998 0.065 Uiso 1 1 calc R . .
C15 C -0.0896(4) -0.2237(2) 0.32514(18) 0.0595(6) Uani 1 1 d . . .
H15 H -0.2156 -0.2174 0.3643 0.071 Uiso 1 1 calc R . .
C16 C -0.0693(4) -0.3450(2) 0.24706(17) 0.0540(5) Uani 1 1 d . . .
C17 C 0.1196(4) -0.3496(2) 0.18973(16) 0.0543(5) Uani 1 1 d . . .
H17 H 0.1371 -0.4297 0.1362 0.065 Uiso 1 1 calc R . .
C18 C 0.2816(4) -0.2387(2) 0.21001(15) 0.0511(5) Uani 1 1 d . . .
H18 H 0.4053 -0.2446 0.1698 0.061 Uiso 1 1 calc R . .
C19 C -0.2421(4) -0.4682(2) 0.2256(2) 0.0781(8) Uani 1 1 d . . .
H19A H -0.2121 -0.5383 0.1636 0.117 Uiso 1 1 calc R . .
H19B H -0.4019 -0.4443 0.2181 0.117 Uiso 1 1 calc R . .
H19C H -0.2224 -0.5005 0.2813 0.117 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'
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
C9 S1 C12 101.30(10) . . ?
C11 O1 C8 107.31(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.76(18) . . ?
C3 C2 C1 121.7(2) . . ?
C7 C2 C1 120.53(19) . . ?
C2 C3 C4 121.57(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 120.63(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 117.66(17) . . ?
C4 C5 C8 121.23(17) . . ?
C6 C5 C8 121.10(17) . . ?
C7 C6 C5 121.16(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 121.19(18) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C9 C8 O1 109.01(16) . . ?
C9 C8 C5 134.59(17) . . ?
O1 C8 C5 116.36(15) . . ?
C8 C9 C10 106.86(17) . . ?
C8 C9 S1 124.90(15) . . ?
C10 C9 S1 128.23(14) . . ?
C11 C10 C9 107.40(16) . . ?
C11 C10 H10 126.3 . . ?
C9 C10 H10 126.3 . . ?
C10 C11 O1 109.42(16) . . ?
C10 C11 C13 133.65(17) . . ?
O1 C11 C13 116.91(16) . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.73(18) . . ?
C14 C13 C11 120.91(18) . . ?
C18 C13 C11 121.36(17) . . ?
C15 C14 C13 120.88(19) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.83(19) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 117.21(19) . . ?
C15 C16 C19 121.7(2) . . ?
C17 C16 C19 121.1(2) . . ?
C18 C17 C16 121.69(19) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 120.64(19) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
S1 C9 1.754(2) . ?
S1 C12 1.791(2) . ?
O1 C11 1.369(2) . ?
O1 C8 1.382(2) . ?
C1 C2 1.514(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.376(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C8 1.457(2) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.359(2) . ?
C9 C10 1.418(3) . ?
C10 C11 1.351(3) . ?
C10 H10 0.9300 . ?
C11 C13 1.455(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.387(3) . ?
C13 C18 1.395(3) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 C19 1.506(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 S1 0.93 2.78 3.3314(19) 119.0 .
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
C7 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 -179.63(19) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 C8 -177.35(17) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C8 C5 C6 C7 177.80(18) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C1 C2 C7 C6 -179.90(19) . . . . ?
C11 O1 C8 C9 0.3(2) . . . . ?
C11 O1 C8 C5 -177.54(16) . . . . ?
C4 C5 C8 C9 32.3(3) . . . . ?
C6 C5 C8 C9 -146.3(2) . . . . ?
C4 C5 C8 O1 -150.55(17) . . . . ?
C6 C5 C8 O1 30.8(3) . . . . ?
O1 C8 C9 C10 0.0(2) . . . . ?
C5 C8 C9 C10 177.3(2) . . . . ?
O1 C8 C9 S1 -179.19(14) . . . . ?
C5 C8 C9 S1 -1.9(3) . . . . ?
C12 S1 C9 C8 159.09(19) . . . . ?
C12 S1 C9 C10 -19.9(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
S1 C9 C10 C11 178.84(16) . . . . ?
C9 C10 C11 O1 0.5(2) . . . . ?
C9 C10 C11 C13 179.0(2) . . . . ?
C8 O1 C11 C10 -0.5(2) . . . . ?
C8 O1 C11 C13 -179.26(17) . . . . ?
C10 C11 C13 C14 26.4(4) . . . . ?
O1 C11 C13 C14 -155.21(18) . . . . ?
C10 C11 C13 C18 -152.7(2) . . . . ?
O1 C11 C13 C18 25.7(3) . . . . ?
C18 C13 C14 C15 1.3(3) . . . . ?
C11 C13 C14 C15 -177.83(19) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C14 C15 C16 C19 178.3(2) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C19 C16 C17 C18 -178.6(2) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C11 C13 C18 C17 177.55(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658667
