#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023374.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_4023374
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 H20 O4 S'
_chemical_formula_sum            'C19 H20 O4 S'
_chemical_formula_weight         344.41
_chemical_name_systematic
; 
 ? 
;
_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                 112.8110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9488(8)
_cell_length_b                   28.804(3)
_cell_length_c                   7.4957(7)
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.15
_cell_measurement_theta_min      3.11
_cell_volume                     1781.0(3)
_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      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10072
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0587
_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)+(0.0734P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1568
_reflns_number_gt                2181
_reflns_number_total             3494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702585s-File003.cif
_cod_data_source_block           t
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023374
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 0.5274(4) 0.14286(13) -0.1427(5) 0.0908(12) Uani 1 1 d . . .
H1A H 0.6125 0.1335 -0.0237 0.136 Uiso 1 1 calc R . .
H1B H 0.5739 0.1561 -0.2270 0.136 Uiso 1 1 calc R . .
H1C H 0.4631 0.1163 -0.2040 0.136 Uiso 1 1 calc R . .
C2 C 0.3581(3) 0.16513(10) 0.0230(4) 0.0518(7) Uani 1 1 d . . .
C3 C 0.2677(4) 0.19964(9) 0.0622(4) 0.0572(8) Uani 1 1 d . . .
H3 H 0.2591 0.2286 0.0038 0.069 Uiso 1 1 calc R . .
C4 C 0.1902(3) 0.19184(9) 0.1863(4) 0.0518(7) Uani 1 1 d . . .
H4 H 0.1276 0.2152 0.2080 0.062 Uiso 1 1 calc R . .
C5 C 0.2049(3) 0.14949(9) 0.2791(3) 0.0435(6) Uani 1 1 d . . .
C6 C 0.2966(3) 0.11509(9) 0.2387(4) 0.0530(7) Uani 1 1 d . . .
H6 H 0.3074 0.0864 0.2990 0.064 Uiso 1 1 calc R . .
C7 C 0.3716(3) 0.12250(9) 0.1117(4) 0.0559(7) Uani 1 1 d . . .
H7 H 0.4312 0.0989 0.0859 0.067 Uiso 1 1 calc R . .
C8 C 0.1276(3) 0.13894(9) 0.4160(4) 0.0511(7) Uani 1 1 d . . .
C9 C 0.0183(3) 0.17540(9) 0.4494(4) 0.0551(7) Uani 1 1 d . . .
H9A H -0.0718 0.1817 0.3282 0.066 Uiso 1 1 calc R . .
H9B H 0.0789 0.2040 0.4924 0.066 Uiso 1 1 calc R . .
C10 C -0.0472(3) 0.15986(8) 0.5997(4) 0.0472(7) Uani 1 1 d . . .
H10 H 0.0453 0.1495 0.7143 0.057 Uiso 1 1 calc R . .
C11 C -0.1631(3) 0.11920(9) 0.5296(4) 0.0453(7) Uani 1 1 d . . .
C12 C -0.1881(3) 0.08837(8) 0.6733(4) 0.0432(6) Uani 1 1 d . . .
C13 C -0.0919(4) 0.08843(9) 0.8680(4) 0.0568(8) Uani 1 1 d . . .
H13 H -0.0073 0.1097 0.9143 0.068 Uiso 1 1 calc R . .
C14 C -0.1160(4) 0.05826(10) 0.9966(4) 0.0618(8) Uani 1 1 d . . .
H14 H -0.0479 0.0589 1.1270 0.074 Uiso 1 1 calc R . .
C15 C -0.2424(4) 0.02696(10) 0.9296(5) 0.0631(8) Uani 1 1 d . . .
C16 C -0.3406(4) 0.02662(11) 0.7375(5) 0.0765(10) Uani 1 1 d . . .
H16 H -0.4267 0.0058 0.6928 0.092 Uiso 1 1 calc R . .
C17 C -0.3148(4) 0.05638(10) 0.6086(4) 0.0618(8) Uani 1 1 d . . .
H17 H -0.3821 0.0552 0.4780 0.074 Uiso 1 1 calc R . .
C18 C -0.1805(6) -0.00522(12) 1.2436(6) 0.1064(15) Uani 1 1 d . . .
H18A H -0.0707 -0.0127 1.2632 0.160 Uiso 1 1 calc R . .
H18B H -0.2217 -0.0282 1.3055 0.160 Uiso 1 1 calc R . .
H18C H -0.1835 0.0247 1.2981 0.160 Uiso 1 1 calc R . .
C19 C -0.3252(4) 0.21653(11) 0.4618(5) 0.0781(10) Uani 1 1 d . . .
H19A H -0.2939 0.2252 0.3575 0.117 Uiso 1 1 calc R . .
H19B H -0.3873 0.2412 0.4857 0.117 Uiso 1 1 calc R . .
H19C H -0.3897 0.1888 0.4276 0.117 Uiso 1 1 calc R . .
O1 O 0.4269(3) 0.17673(7) -0.1029(3) 0.0749(6) Uani 1 1 d . . .
O2 O 0.1468(3) 0.10183(7) 0.4992(3) 0.0754(7) Uani 1 1 d . . .
O3 O -0.2391(2) 0.11383(7) 0.3566(3) 0.0638(6) Uani 1 1 d . . .
O4 O -0.2775(3) -0.00451(8) 1.0419(4) 0.0933(8) Uani 1 1 d . . .
S1 S -0.14725(10) 0.20616(2) 0.67576(12) 0.0609(3) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 125.3(2) . . ?
O1 C2 C3 115.6(2) . . ?
C7 C2 C3 119.1(2) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 117.8(2) . . ?
C4 C5 C8 123.5(2) . . ?
C6 C5 C8 118.7(2) . . ?
C7 C6 C5 121.8(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
O2 C8 C5 121.8(2) . . ?
O2 C8 C9 119.7(2) . . ?
C5 C8 C9 118.5(2) . . ?
C8 C9 C10 112.0(2) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 112.2(2) . . ?
C11 C10 S1 108.76(17) . . ?
C9 C10 S1 113.18(17) . . ?
C11 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
S1 C10 H10 107.5 . . ?
O3 C11 C12 121.3(2) . . ?
O3 C11 C10 119.4(2) . . ?
C12 C11 C10 119.2(2) . . ?
C13 C12 C17 117.4(2) . . ?
C13 C12 C11 124.2(2) . . ?
C17 C12 C11 118.4(2) . . ?
C14 C13 C12 122.6(3) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
O4 C15 C16 116.2(3) . . ?
O4 C15 C14 124.5(3) . . ?
C16 C15 C14 119.3(3) . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C12 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 O1 C1 117.9(2) . . ?
C15 O4 C18 118.5(3) . . ?
C19 S1 C10 102.50(13) . . ?
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 O1 1.434(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.354(3) . ?
C2 C7 1.379(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C8 1.474(4) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.216(3) . ?
C8 C9 1.520(4) . ?
C9 C10 1.525(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.517(3) . ?
C10 S1 1.817(3) . ?
C10 H10 0.9800 . ?
C11 O3 1.218(3) . ?
C11 C12 1.479(3) . ?
C12 C13 1.377(3) . ?
C12 C17 1.394(4) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 O4 1.355(3) . ?
C15 C16 1.366(4) . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O4 1.422(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 S1 1.794(3) . ?
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
C18 H18B O2 0.96 2.52 3.332(4) 142.8 3_557
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
O1 C2 C3 C4 179.3(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
C3 C4 C5 C8 179.0(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C8 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
O1 C2 C7 C6 179.5(3) . . . . ?
C3 C2 C7 C6 -0.6(4) . . . . ?
C4 C5 C8 O2 -177.8(3) . . . . ?
C6 C5 C8 O2 2.8(4) . . . . ?
C4 C5 C8 C9 3.5(4) . . . . ?
C6 C5 C8 C9 -175.9(2) . . . . ?
O2 C8 C9 C10 3.3(4) . . . . ?
C5 C8 C9 C10 -178.0(2) . . . . ?
C8 C9 C10 C11 -67.0(3) . . . . ?
C8 C9 C10 S1 169.44(18) . . . . ?
C9 C10 C11 O3 -26.9(3) . . . . ?
S1 C10 C11 O3 99.0(2) . . . . ?
C9 C10 C11 C12 156.4(2) . . . . ?
S1 C10 C11 C12 -77.7(3) . . . . ?
O3 C11 C12 C13 170.8(3) . . . . ?
C10 C11 C12 C13 -12.5(4) . . . . ?
O3 C11 C12 C17 -7.7(4) . . . . ?
C10 C11 C12 C17 168.9(2) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
C11 C12 C13 C14 -178.0(3) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 O4 179.6(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
O4 C15 C16 C17 -178.7(3) . . . . ?
C14 C15 C16 C17 0.9(5) . . . . ?
C15 C16 C17 C12 -1.1(5) . . . . ?
C13 C12 C17 C16 0.4(4) . . . . ?
C11 C12 C17 C16 179.0(3) . . . . ?
C7 C2 O1 C1 -2.5(4) . . . . ?
C3 C2 O1 C1 177.5(3) . . . . ?
C16 C15 O4 C18 -179.1(3) . . . . ?
C14 C15 O4 C18 1.2(4) . . . . ?
C11 C10 S1 C19 -57.1(2) . . . . ?
C9 C10 S1 C19 68.3(2) . . . . ?
