#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/59/1505964.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_1505964
loop_
_publ_author_name
'Yin, Guodong'
'Zhou, Baohan'
'Meng, Xianggao'
'Wu, Anxin'
'Pan, Yuanjiang'
_publ_section_title
;
 Efficient C-C double-bond formation reaction via a new synthetic
 strategy: a self-sorting tandem reaction.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2245
_journal_page_last               2248
_journal_paper_doi               10.1021/ol060541e
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C17 H14 O2 S'
_chemical_formula_sum            'C17 H14 O2 S'
_chemical_formula_weight         282.34
_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                 105.982(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6295(9)
_cell_length_b                   10.5087(10)
_cell_length_c                   15.1393(14)
_cell_measurement_reflns_used    5817
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1472.8(2)
_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      292(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9992
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0428
_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)+(0.0698P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2832
_reflns_number_total             3477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060541esi20060305_075825.cif
_cod_data_source_block           l:\050726e-E-isomer
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505964
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
S1 S 1.04341(4) 0.87338(4) 0.18192(3) 0.06496(16) Uani 1 1 d .
C8 C 0.91543(14) 0.64157(12) 0.12946(9) 0.0505(3) Uani 1 1 d .
H8 H 1.0059 0.6034 0.1486 0.061 Uiso 1 1 calc R
C9 C 0.90304(13) 0.76779(12) 0.13771(8) 0.0479(3) Uani 1 1 d .
O2 O 0.66638(11) 0.60829(10) 0.08034(8) 0.0689(3) Uani 1 1 d .
O1 O 0.72165(13) 0.87267(10) 0.02424(7) 0.0695(3) Uani 1 1 d .
C7 C 0.78710(13) 0.56330(12) 0.09043(9) 0.0492(3) Uani 1 1 d .
C11 C 0.68770(14) 0.87969(12) 0.17340(9) 0.0523(3) Uani 1 1 d .
C10 C 0.76155(15) 0.83992(12) 0.10389(9) 0.0513(3) Uani 1 1 d .
C1 C 0.93742(16) 0.37133(13) 0.07385(10) 0.0561(3) Uani 1 1 d .
H1 H 1.0217 0.4181 0.0965 0.067 Uiso 1 1 calc R
C6 C 0.80411(14) 0.42896(12) 0.06374(8) 0.0481(3) Uani 1 1 d .
C5 C 0.67933(17) 0.35830(14) 0.02737(10) 0.0606(4) Uani 1 1 d .
H5 H 0.5892 0.3960 0.0189 0.073 Uiso 1 1 calc R
C3 C 0.8210(2) 0.17568(16) 0.01577(12) 0.0764(5) Uani 1 1 d .
H3 H 0.8266 0.0905 0.0005 0.092 Uiso 1 1 calc R
C17 C 1.19648(17) 0.77187(19) 0.22201(13) 0.0790(5) Uani 1 1 d .
H17A H 1.1798 0.7145 0.2673 0.118 Uiso 1 1 calc R
H17B H 1.2805 0.8225 0.2488 0.118 Uiso 1 1 calc R
H17C H 1.2115 0.7240 0.1714 0.118 Uiso 1 1 calc R
C16 C 0.58740(18) 0.97783(15) 0.15229(14) 0.0714(4) Uani 1 1 d .
H16 H 0.5642 1.0155 0.0945 0.086 Uiso 1 1 calc R
C13 C 0.6509(2) 0.8640(2) 0.32414(13) 0.0841(6) Uani 1 1 d .
H13 H 0.6707 0.8247 0.3813 0.101 Uiso 1 1 calc R
C12 C 0.71883(16) 0.82288(17) 0.25961(10) 0.0651(4) Uani 1 1 d .
H12 H 0.7856 0.7569 0.2741 0.078 Uiso 1 1 calc R
C4 C 0.6890(2) 0.23212(16) 0.00373(12) 0.0749(5) Uani 1 1 d .
H4 H 0.6052 0.1853 -0.0205 0.090 Uiso 1 1 calc R
C2 C 0.94551(19) 0.24480(15) 0.05038(11) 0.0682(4) Uani 1 1 d .
H2 H 1.0351 0.2065 0.0580 0.082 Uiso 1 1 calc R
C14 C 0.5548(2) 0.9624(2) 0.30353(17) 0.0952(7) Uani 1 1 d .
H14 H 0.5110 0.9914 0.3473 0.114 Uiso 1 1 calc R
C15 C 0.5223(2) 1.01908(19) 0.21798(19) 0.0929(6) Uani 1 1 d .
H15 H 0.4561 1.0856 0.2044 0.111 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
C9 S1 C17 103.40(8)
C9 C8 C7 120.38(12)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 123.83(12)
C8 C9 S1 126.09(11)
C10 C9 S1 110.00(9)
O2 C7 C8 119.95(12)
O2 C7 C6 120.22(12)
C8 C7 C6 119.82(11)
C16 C11 C12 119.43(14)
C16 C11 C10 119.00(14)
C12 C11 C10 121.56(13)
O1 C10 C11 122.96(13)
O1 C10 C9 119.13(12)
C11 C10 C9 117.52(11)
C2 C1 C6 120.41(14)
C2 C1 H1 119.8
C6 C1 H1 119.8
C1 C6 C5 118.84(13)
C1 C6 C7 123.40(11)
C5 C6 C7 117.76(12)
C4 C5 C6 120.14(15)
C4 C5 H5 119.9
C6 C5 H5 119.9
C4 C3 C2 120.13(15)
C4 C3 H3 119.9
C2 C3 H3 119.9
S1 C17 H17A 109.5
S1 C17 H17B 109.5
H17A C17 H17B 109.5
S1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C16 C11 119.43(19)
C15 C16 H16 120.3
C11 C16 H16 120.3
C14 C13 C12 119.79(19)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C12 C11 120.40(17)
C13 C12 H12 119.8
C11 C12 H12 119.8
C3 C4 C5 120.44(15)
C3 C4 H4 119.8
C5 C4 H4 119.8
C3 C2 C1 120.02(16)
C3 C2 H2 120.0
C1 C2 H2 120.0
C13 C14 C15 120.35(17)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C16 120.58(19)
C14 C15 H15 119.7
C16 C15 H15 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.7344(13)
S1 C17 1.7851(19)
C8 C9 1.3406(18)
C8 C7 1.4665(17)
C8 H8 0.9300
C9 C10 1.5196(18)
O2 C7 1.2249(16)
O1 C10 1.2104(16)
C7 C6 1.4899(19)
C11 C16 1.389(2)
C11 C12 1.391(2)
C11 C10 1.4832(19)
C1 C2 1.384(2)
C1 C6 1.389(2)
C1 H1 0.9300
C6 C5 1.3907(18)
C5 C4 1.383(2)
C5 H5 0.9300
C3 C4 1.369(3)
C3 C2 1.376(2)
C3 H3 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C16 C15 1.383(3)
C16 H16 0.9300
C13 C14 1.365(3)
C13 C12 1.386(2)
C13 H13 0.9300
C12 H12 0.9300
C4 H4 0.9300
C2 H2 0.9300
C14 C15 1.381(3)
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
C14 H14 O2 0.93 2.58 3.470(2) 160.4 2_655
C5 H5 O2 0.93 2.51 3.2978(18) 143.1 3_665
C3 H3 O1 0.93 2.57 3.338(2) 140.5 1_545
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
C7 C8 C9 C10 -3.4(2)
C7 C8 C9 S1 -179.84(9)
C17 S1 C9 C8 -5.57(14)
C17 S1 C9 C10 177.58(10)
C9 C8 C7 O2 -13.0(2)
C9 C8 C7 C6 167.43(12)
C16 C11 C10 O1 -13.3(2)
C12 C11 C10 O1 168.07(14)
C16 C11 C10 C9 159.44(12)
C12 C11 C10 C9 -19.18(18)
C8 C9 C10 O1 -84.42(17)
S1 C9 C10 O1 92.51(13)
C8 C9 C10 C11 102.54(15)
S1 C9 C10 C11 -80.53(12)
C2 C1 C6 C5 -1.7(2)
C2 C1 C6 C7 177.90(13)
O2 C7 C6 C1 -179.49(13)
C8 C7 C6 C1 0.12(19)
O2 C7 C6 C5 0.13(19)
C8 C7 C6 C5 179.74(11)
C1 C6 C5 C4 1.4(2)
C7 C6 C5 C4 -178.27(14)
C12 C11 C16 C15 1.3(2)
C10 C11 C16 C15 -177.38(15)
C14 C13 C12 C11 -1.2(3)
C16 C11 C12 C13 -0.2(2)
C10 C11 C12 C13 178.38(14)
C2 C3 C4 C5 -0.9(3)
C6 C5 C4 C3 -0.1(2)
C4 C3 C2 C1 0.6(2)
C6 C1 C2 C3 0.8(2)
C12 C13 C14 C15 1.6(3)
C13 C14 C15 C16 -0.6(3)
C11 C16 C15 C14 -0.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199834
