#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:54:16 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/29/4032922.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_4032922
loop_
_publ_author_name
'Chen, Daoliang'
'Yuan, Dafei'
'Zhang, Cheng'
'Wu, Hao'
'Zhang, Jianyun'
'Li, Baolin'
'Zhu, Xiaozhang'
_publ_section_title
;
 Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan
 Derivatives with up to Six Fused Rings.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10920
_journal_page_last               10927
_journal_paper_doi               10.1021/acs.joc.7b01745
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C30 H38 O2 S2'
_chemical_formula_sum            'C30 H38 O2 S2'
_chemical_formula_weight         494.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                94.123(7)
_cell_angle_beta                 92.155(4)
_cell_angle_gamma                108.359(8)
_cell_formula_units_Z            1
_cell_length_a                   6.657(3)
_cell_length_b                   8.177(4)
_cell_length_c                   12.851(5)
_cell_measurement_reflns_used    2013
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4841
_cell_measurement_theta_min      2.6350
_cell_volume                     660.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9537
              2theta: -20.0675
scan:
    Number of images: 336
               Slice: -110.0000 - 58.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 44.9537
              2theta: -20.0675
scan:
    Number of images: 318
               Slice: -100.2500 - 58.7500
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9537
              2theta: -20.0675
scan:
    Number of images: 240
               Slice: -110.0000 - 10.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.9537
              2theta: -20.0675
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1419
_diffrn_orient_matrix_UB_12      -0.0708
_diffrn_orient_matrix_UB_13      0.0022
_diffrn_orient_matrix_UB_21      0.0131
_diffrn_orient_matrix_UB_22      -0.1170
_diffrn_orient_matrix_UB_23      0.0537
_diffrn_orient_matrix_UB_31      -0.0163
_diffrn_orient_matrix_UB_32      0.0239
_diffrn_orient_matrix_UB_33      0.0726
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9042
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.635
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       Plate
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0363P)²+0.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01745_si_002.cif
_cod_data_source_block           mx5205_C8DTBDF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032919--4032922.cif.
;
_cod_original_cell_volume        660.8(5)
_cod_database_code               4032922
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_number_total             3013
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
S1 S -0.36076(6) 0.50241(5) 0.36874(3) 0.02815(13) Uani 1 1 d .
O1 O -0.10843(17) 0.16074(14) 0.43285(9) 0.0272(3) Uani 1 1 d .
C1 C -0.5476(2) -0.15997(19) 0.54143(11) 0.0229(3) Uani 1 1 d .
C2 C -0.3428(2) -0.0878(2) 0.50934(12) 0.0246(3) Uani 1 1 d .
H2 H -0.2403 -0.1426 0.5149 0.030 Uiso 1 1 calc R
C3 C -0.3029(2) 0.0697(2) 0.46904(12) 0.0234(3) Uani 1 1 d .
C4 C -0.1374(2) 0.3088(2) 0.39975(12) 0.0254(3) Uani 1 1 d .
C5 C -0.3373(2) 0.31450(19) 0.41289(12) 0.0239(3) Uani 1 1 d .
C6 C -0.0978(3) 0.5664(2) 0.33243(12) 0.0271(3) Uani 1 1 d .
C7 C 0.0023(3) 0.4493(2) 0.35460(12) 0.0271(3) Uani 1 1 d .
H7 H 0.1425 0.4607 0.3417 0.033 Uiso 1 1 calc R
C8 C -0.0100(3) 0.7323(2) 0.28189(14) 0.0313(4) Uani 1 1 d .
H8A H -0.0208 0.8276 0.3284 0.038 Uiso 1 1 calc R
H8B H -0.0947 0.7271 0.2179 0.038 Uiso 1 1 calc R
C9 C 0.2211(3) 0.7670(2) 0.25657(13) 0.0283(3) Uani 1 1 d .
H9A H 0.3047 0.7716 0.3208 0.034 Uiso 1 1 calc R
H9B H 0.2309 0.6708 0.2106 0.034 Uiso 1 1 calc R
C10 C 0.3170(3) 0.9339(2) 0.20490(13) 0.0291(4) Uani 1 1 d .
H10A H 0.2363 0.9295 0.1397 0.035 Uiso 1 1 calc R
H10B H 0.3077 1.0310 0.2502 0.035 Uiso 1 1 calc R
C11 C 0.5472(3) 0.9614(2) 0.18314(13) 0.0300(4) Uani 1 1 d .
H11A H 0.5544 0.8641 0.1373 0.036 Uiso 1 1 calc R
H11B H 0.6253 0.9616 0.2485 0.036 Uiso 1 1 calc R
C12 C 0.6564(3) 1.1276(2) 0.13353(13) 0.0300(4) Uani 1 1 d .
H12A H 0.5837 1.1250 0.0663 0.036 Uiso 1 1 calc R
H12B H 0.6439 1.2250 0.1775 0.036 Uiso 1 1 calc R
C13 C 0.8894(3) 1.1550(2) 0.11799(14) 0.0328(4) Uani 1 1 d .
H13A H 0.9020 1.0571 0.0745 0.039 Uiso 1 1 calc R
H13B H 0.9623 1.1586 0.1853 0.039 Uiso 1 1 calc R
C14 C 0.9978(3) 1.3202(2) 0.06752(14) 0.0359(4) Uani 1 1 d .
H14A H 0.9757 1.4170 0.1081 0.043 Uiso 1 1 calc R
H14B H 0.9315 1.3126 -0.0020 0.043 Uiso 1 1 calc R
C15 C 1.2348(3) 1.3556(3) 0.05901(19) 0.0533(6) Uani 1 1 d .
H15A H 1.2581 1.2633 0.0158 0.080 Uiso 1 1 calc GR
H15B H 1.3019 1.3630 0.1274 0.080 Uiso 1 1 calc GR
H15C H 1.2939 1.4628 0.0284 0.080 Uiso 1 1 calc GR
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
C5 S1 C6 91.54(7) . .
C4 O1 C3 104.54(12) . .
C2 C1 C3 119.55(14) . 2_456
C2 C1 C5 136.48(14) . 2_456
C3 C1 C5 103.97(13) 2_456 2_456
C1 C2 H2 122.3 . .
C3 C2 C1 115.50(13) . .
C3 C2 H2 122.3 . .
O1 C3 C1 111.46(13) . 2_456
C2 C3 O1 123.59(13) . .
C2 C3 C1 124.95(14) . 2_456
O1 C4 C7 130.81(14) . .
C5 C4 O1 112.49(13) . .
C5 C4 C7 116.70(14) . .
C1 C5 S1 142.94(12) 2_456 .
C4 C5 S1 109.52(11) . .
C4 C5 C1 107.54(13) . 2_456
C7 C6 S1 112.09(12) . .
C7 C6 C8 127.99(15) . .
C8 C6 S1 119.92(12) . .
C4 C7 H7 124.9 . .
C6 C7 C4 110.16(14) . .
C6 C7 H7 124.9 . .
C6 C8 H8A 109.1 . .
C6 C8 H8B 109.1 . .
C6 C8 C9 112.46(14) . .
H8A C8 H8B 107.8 . .
C9 C8 H8A 109.1 . .
C9 C8 H8B 109.1 . .
C8 C9 H9A 108.7 . .
C8 C9 H9B 108.7 . .
H9A C9 H9B 107.6 . .
C10 C9 C8 114.38(14) . .
C10 C9 H9A 108.7 . .
C10 C9 H9B 108.7 . .
C9 C10 H10A 109.3 . .
C9 C10 H10B 109.3 . .
H10A C10 H10B 108.0 . .
C11 C10 C9 111.58(14) . .
C11 C10 H10A 109.3 . .
C11 C10 H10B 109.3 . .
C10 C11 H11A 108.6 . .
C10 C11 H11B 108.6 . .
C10 C11 C12 114.86(14) . .
H11A C11 H11B 107.5 . .
C12 C11 H11A 108.6 . .
C12 C11 H11B 108.6 . .
C11 C12 H12A 108.9 . .
C11 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C13 C12 C11 113.33(14) . .
C13 C12 H12A 108.9 . .
C13 C12 H12B 108.9 . .
C12 C13 H13A 108.9 . .
C12 C13 H13B 108.9 . .
C12 C13 C14 113.29(14) . .
H13A C13 H13B 107.7 . .
C14 C13 H13A 108.9 . .
C14 C13 H13B 108.9 . .
C13 C14 H14A 108.8 . .
C13 C14 H14B 108.8 . .
C13 C14 C15 113.68(16) . .
H14A C14 H14B 107.7 . .
C15 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C5 1.7253(16) .
S1 C6 1.7535(18) .
O1 C3 1.3905(18) .
O1 C4 1.3783(19) .
C1 C2 1.395(2) .
C1 C3 1.421(2) 2_456
C1 C5 1.435(2) 2_456
C2 H2 0.9300 .
C2 C3 1.374(2) .
C3 C1 1.421(2) 2_456
C4 C5 1.362(2) .
C4 C7 1.409(2) .
C5 C1 1.435(2) 2_456
C6 C7 1.367(2) .
C6 C8 1.503(2) .
C7 H7 0.9300 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C9 1.526(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.524(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 C11 1.517(2) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.523(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.519(2) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.521(2) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.521(3) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
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_4
S1 C6 C7 C4 0.61(18) . .
S1 C6 C8 C9 179.60(12) . .
O1 C4 C5 S1 -179.53(10) . .
O1 C4 C5 C1 0.29(18) . 2_456
O1 C4 C7 C6 178.83(16) . .
C1 C2 C3 O1 -179.78(13) . .
C1 C2 C3 C1 0.0(3) . 2_456
C3 O1 C4 C5 -0.22(17) . .
C3 O1 C4 C7 -179.24(16) . .
C3 C1 C2 C3 0.0(2) 2_456 .
C4 O1 C3 C1 0.07(17) . 2_456
C4 O1 C3 C2 179.89(15) . .
C5 S1 C6 C7 -0.70(13) . .
C5 S1 C6 C8 178.52(14) . .
C5 C1 C2 C3 -179.61(17) 2_456 .
C5 C4 C7 C6 -0.2(2) . .
C6 S1 C5 C1 -179.1(2) . 2_456
C6 S1 C5 C4 0.59(13) . .
C6 C8 C9 C10 179.85(14) . .
C7 C4 C5 S1 -0.37(19) . .
C7 C4 C5 C1 179.45(14) . 2_456
C7 C6 C8 C9 -1.3(2) . .
C8 C6 C7 C4 -178.55(16) . .
C8 C9 C10 C11 179.31(14) . .
C9 C10 C11 C12 -178.77(13) . .
C10 C11 C12 C13 177.08(14) . .
C11 C12 C13 C14 179.47(14) . .
C12 C13 C14 C15 175.71(16) . .
