#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023372.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_4023372
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         'C15 H11 Cl O2 S2'
_chemical_formula_sum            'C15 H11 Cl O2 S2'
_chemical_formula_weight         322.81
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5655(6)
_cell_length_b                   10.4556(6)
_cell_length_c                   27.2783(15)
_cell_measurement_reflns_used    4357
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.44
_cell_volume                     3013.4(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            20201
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0681
_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)+(0.0640P)²+1.7734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                2799
_reflns_number_total             3289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702585s-File001.cif
_cod_data_source_block           t
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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     -P2ac2ab
_cod_database_code               4023372
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 1.0865(3) 0.4174(3) 0.62064(15) 0.0609(9) Uani 1 1 d . . .
C2 C 1.0101(4) 0.4052(3) 0.58051(15) 0.0697(11) Uani 1 1 d . . .
H2 H 0.9989 0.3257 0.5658 0.084 Uiso 1 1 calc R . .
C3 C 0.9499(4) 0.5114(3) 0.56208(13) 0.0608(9) Uani 1 1 d . . .
H3 H 0.8983 0.5038 0.5346 0.073 Uiso 1 1 calc R . .
C4 C 0.9658(3) 0.6302(3) 0.58423(11) 0.0453(7) Uani 1 1 d . . .
C5 C 1.0414(3) 0.6396(3) 0.62536(12) 0.0500(7) Uani 1 1 d . . .
H5 H 1.0510 0.7182 0.6409 0.060 Uiso 1 1 calc R . .
C6 C 1.1033(3) 0.5327(3) 0.64369(13) 0.0584(8) Uani 1 1 d . . .
H6 H 1.1551 0.5391 0.6711 0.070 Uiso 1 1 calc R . .
C7 C 0.9039(3) 0.7451(3) 0.56306(11) 0.0510(7) Uani 1 1 d . . .
C8 C 0.9005(3) 0.8659(3) 0.59354(10) 0.0436(7) Uani 1 1 d . . .
C9 C 1.1206(4) 0.9090(4) 0.53985(14) 0.0786(12) Uani 1 1 d . . .
H9A H 1.1580 0.8357 0.5554 0.118 Uiso 1 1 calc R . .
H9B H 1.1859 0.9685 0.5310 0.118 Uiso 1 1 calc R . .
H9C H 1.0759 0.8824 0.5109 0.118 Uiso 1 1 calc R . .
C10 C 0.8084(3) 0.8732(3) 0.62709(10) 0.0439(6) Uani 1 1 d . . .
H10 H 0.7556 0.8029 0.6312 0.053 Uiso 1 1 calc R . .
C11 C 0.7864(2) 0.9858(2) 0.65772(10) 0.0384(6) Uani 1 1 d . . .
C12 C 0.6973(3) 0.9738(2) 0.69856(10) 0.0392(6) Uani 1 1 d . . .
C13 C 0.5696(3) 1.0239(3) 0.77122(13) 0.0625(9) Uani 1 1 d . . .
H13 H 0.5291 1.0589 0.7983 0.075 Uiso 1 1 calc R . .
C14 C 0.5497(3) 0.9026(3) 0.75505(13) 0.0600(8) Uani 1 1 d . . .
H14 H 0.4941 0.8452 0.7697 0.072 Uiso 1 1 calc R . .
C15 C 0.6233(3) 0.8739(3) 0.71334(11) 0.0466(7) Uani 1 1 d . . .
H15 H 0.6216 0.7952 0.6975 0.056 Uiso 1 1 calc R . .
Cl1 Cl 1.16252(11) 0.28320(10) 0.64390(6) 0.0993(4) Uani 1 1 d . . .
O1 O 0.8553(3) 0.7448(3) 0.52298(9) 0.0855(9) Uani 1 1 d . . .
O2 O 0.8435(2) 1.08687(18) 0.65032(8) 0.0506(5) Uani 1 1 d . . .
S1 S 0.67647(8) 1.10438(7) 0.73648(3) 0.0546(3) Uani 1 1 d . . .
S2 S 1.01120(9) 0.98508(9) 0.58191(3) 0.0603(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'
Cl Cl 0.1484 0.1585 '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 C6 121.8(3) . . ?
C2 C1 Cl1 119.4(3) . . ?
C6 C1 Cl1 118.9(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 C7 120.9(3) . . ?
C3 C4 C7 120.0(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 C4 122.5(3) . . ?
O1 C7 C8 119.3(3) . . ?
C4 C7 C8 118.2(2) . . ?
C10 C8 C7 116.1(3) . . ?
C10 C8 S2 125.0(2) . . ?
C7 C8 S2 118.9(2) . . ?
S2 C9 H9A 109.5 . . ?
S2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 123.6(3) . . ?
C8 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
O2 C11 C10 121.2(3) . . ?
O2 C11 C12 120.8(2) . . ?
C10 C11 C12 118.0(2) . . ?
C15 C12 C11 131.2(2) . . ?
C15 C12 S1 110.8(2) . . ?
C11 C12 S1 118.1(2) . . ?
C14 C13 S1 112.6(3) . . ?
C14 C13 H13 123.7 . . ?
S1 C13 H13 123.7 . . ?
C13 C14 C15 112.0(3) . . ?
C13 C14 H14 124.0 . . ?
C15 C14 H14 124.0 . . ?
C12 C15 C14 113.1(3) . . ?
C12 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C13 S1 C12 91.57(15) . . ?
C8 S2 C9 103.31(18) . . ?
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 1.366(6) . ?
C1 C6 1.371(5) . ?
C1 Cl1 1.737(3) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 C7 1.485(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.208(4) . ?
C7 C8 1.513(4) . ?
C8 C10 1.338(4) . ?
C8 S2 1.738(3) . ?
C9 S2 1.813(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.462(4) . ?
C10 H10 0.9300 . ?
C11 O2 1.234(3) . ?
C11 C12 1.463(4) . ?
C12 C15 1.366(4) . ?
C12 S1 1.727(3) . ?
C13 C14 1.359(5) . ?
C13 S1 1.697(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.410(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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
C10 H10 O2 0.93 2.54 3.456(4) 166.9 8_755
C13 H13 O2 0.93 2.43 3.275(4) 151.4 6_557
C15 H15 O2 0.93 2.56 3.477(3) 170.2 8_755
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
C6 C1 C2 C3 1.1(5) . . . . ?
Cl1 C1 C2 C3 -180.0(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C2 C3 C4 C7 178.0(3) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
C7 C4 C5 C6 -177.3(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
Cl1 C1 C6 C5 -179.4(2) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C5 C4 C7 O1 167.1(3) . . . . ?
C3 C4 C7 O1 -11.6(5) . . . . ?
C5 C4 C7 C8 -13.7(4) . . . . ?
C3 C4 C7 C8 167.5(3) . . . . ?
O1 C7 C8 C10 97.0(4) . . . . ?
C4 C7 C8 C10 -82.2(4) . . . . ?
O1 C7 C8 S2 -81.4(4) . . . . ?
C4 C7 C8 S2 99.4(3) . . . . ?
C7 C8 C10 C11 -176.3(3) . . . . ?
S2 C8 C10 C11 2.0(4) . . . . ?
C8 C10 C11 O2 8.3(4) . . . . ?
C8 C10 C11 C12 -169.7(3) . . . . ?
O2 C11 C12 C15 179.0(3) . . . . ?
C10 C11 C12 C15 -2.9(4) . . . . ?
O2 C11 C12 S1 -0.9(3) . . . . ?
C10 C11 C12 S1 177.1(2) . . . . ?
S1 C13 C14 C15 0.1(4) . . . . ?
C11 C12 C15 C14 -179.8(3) . . . . ?
S1 C12 C15 C14 0.2(3) . . . . ?
C13 C14 C15 C12 -0.2(4) . . . . ?
C14 C13 S1 C12 0.0(3) . . . . ?
C15 C12 S1 C13 -0.1(2) . . . . ?
C11 C12 S1 C13 179.9(2) . . . . ?
C10 C8 S2 C9 172.1(3) . . . . ?
C7 C8 S2 C9 -9.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658666
