#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/81/1518130.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_1518130
loop_
_publ_author_name
'Inami, Tasuku'
'Kurahashi, Takuya'
'Matsubara, Seijiro'
_publ_section_title
;
 Nickel-catalyzed reaction of thioisatins and alkynes: a facile synthesis
 of thiochromones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5660
_journal_page_last               5662
_journal_paper_doi               10.1021/ol5026102
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C13 H16 O S Si'
_chemical_formula_weight         248.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.609(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.310(5)
_cell_length_b                   15.202(11)
_cell_length_c                   12.490(9)
_cell_measurement_reflns_used    1487
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.86
_cell_measurement_theta_min      2.68
_cell_volume                     1386.5(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      273(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8340
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0696
_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)+(0.1210P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2254
_reflns_number_gt                1677
_reflns_number_total             3054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5026102_si_002.cif
_cod_data_source_block           3ac
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518126--1518130.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1518130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.2295(4) 0.79101(15) 0.36903(17) 0.0992(9) Uani 1 1 d .
C1 C 0.2471(4) 0.94360(18) 0.3692(2) 0.0674(8) Uani 1 1 d .
C2 C 0.2363(4) 0.8595(2) 0.4248(2) 0.0693(8) Uani 1 1 d .
C3 C 0.2324(4) 0.8516(2) 0.5410(2) 0.0694(8) Uani 1 1 d .
C4 C 0.2536(4) 1.0230(2) 0.4223(3) 0.0777(9) Uani 1 1 d .
C5 C 0.2357(4) 0.9242(3) 0.6031(3) 0.0816(10) Uani 1 1 d .
C6 C 0.2642(5) 1.1020(2) 0.3622(4) 0.1067(13) Uani 1 1 d .
H6 H 0.2670 1.1560 0.3973 0.128 Uiso 1 1 calc R
C7 C 0.2540(5) 0.9450(2) 0.2581(3) 0.0897(10) Uani 1 1 d .
H7 H 0.2495 0.8919 0.2211 0.108 Uiso 1 1 calc R
C8 C 0.2293(6) 0.9242(4) 0.7247(3) 0.1230(16) Uani 1 1 d .
H8A H 0.1167 0.8980 0.7453 0.185 Uiso 1 1 calc R
H8B H 0.2363 0.9836 0.7507 0.185 Uiso 1 1 calc R
H8C H 0.3308 0.8910 0.7549 0.185 Uiso 1 1 calc R
C9 C 0.0149(6) 0.6798(3) 0.5228(3) 0.1086(13) Uani 1 1 d .
H9A H 0.0006 0.6959 0.4485 0.163 Uiso 1 1 calc R
H9B H -0.0899 0.6992 0.5599 0.163 Uiso 1 1 calc R
H9C H 0.0256 0.6170 0.5287 0.163 Uiso 1 1 calc R
C10 C 0.2701(6) 1.0989(3) 0.2549(5) 0.1277(17) Uani 1 1 d .
H10 H 0.2766 1.1510 0.2163 0.153 Uiso 1 1 calc R
C11 C 0.2668(7) 1.0204(3) 0.2019(4) 0.1221(16) Uani 1 1 d .
H11 H 0.2733 1.0188 0.1278 0.147 Uiso 1 1 calc R
C12 C 0.2129(10) 0.7128(4) 0.7290(4) 0.188(3) Uani 1 1 d .
H12A H 0.1939 0.6513 0.7418 0.281 Uiso 1 1 calc R
H12B H 0.1134 0.7459 0.7563 0.281 Uiso 1 1 calc R
H12C H 0.3258 0.7311 0.7645 0.281 Uiso 1 1 calc R
C13 C 0.4322(6) 0.6761(3) 0.5393(4) 0.1383(18) Uani 1 1 d .
H13A H 0.4104 0.6139 0.5352 0.207 Uiso 1 1 calc R
H13B H 0.5321 0.6876 0.5899 0.207 Uiso 1 1 calc R
H13C H 0.4623 0.6976 0.4700 0.207 Uiso 1 1 calc R
S1 S 0.24657(12) 1.03189(6) 0.55900(9) 0.0925(4) Uani 1 1 d .
Si1 Si 0.22398(16) 0.73224(7) 0.58289(8) 0.0911(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.173(3) 0.0537(14) 0.0723(14) -0.0082(11) 0.0173(14) -0.0039(14)
C1 0.0691(19) 0.0501(16) 0.083(2) -0.0002(14) 0.0099(15) 0.0011(13)
C2 0.085(2) 0.0488(17) 0.0744(19) -0.0053(13) 0.0073(15) 0.0007(14)
C3 0.072(2) 0.0675(19) 0.0683(17) -0.0044(14) -0.0018(13) 0.0052(15)
C4 0.069(2) 0.0524(19) 0.112(3) -0.0073(16) 0.0106(17) 0.0018(14)
C5 0.071(2) 0.091(3) 0.082(2) -0.0215(18) -0.0039(15) 0.0084(17)
C6 0.097(3) 0.052(2) 0.173(4) -0.002(2) 0.027(3) -0.0019(18)
C7 0.114(3) 0.071(2) 0.086(2) 0.0140(17) 0.0200(19) 0.0025(19)
C8 0.136(4) 0.151(4) 0.081(3) -0.033(3) -0.002(2) 0.007(3)
C9 0.124(3) 0.089(3) 0.116(3) 0.005(2) 0.027(2) -0.013(2)
C10 0.135(4) 0.088(3) 0.163(5) 0.044(3) 0.045(3) 0.008(3)
C11 0.155(4) 0.088(3) 0.126(4) 0.036(3) 0.040(3) 0.008(3)
C12 0.323(9) 0.148(5) 0.090(3) 0.047(3) -0.012(4) -0.011(5)
C13 0.135(4) 0.079(3) 0.199(5) 0.014(3) -0.023(3) 0.023(3)
S1 0.0868(7) 0.0683(6) 0.1220(8) -0.0375(5) 0.0010(5) 0.0029(4)
Si1 0.1189(10) 0.0729(7) 0.0807(7) 0.0160(5) -0.0029(6) 0.0024(5)
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'
Si Si 0.0817 0.0704 '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
C4 C1 C7 117.8(3)
C4 C1 C2 122.7(3)
C7 C1 C2 119.6(3)
O1 C2 C3 118.9(3)
O1 C2 C1 117.7(3)
C3 C2 C1 123.4(3)
C5 C3 C2 120.2(3)
C5 C3 Si1 128.8(3)
C2 C3 Si1 110.9(2)
C1 C4 C6 119.2(4)
C1 C4 S1 123.1(3)
C6 C4 S1 117.6(3)
C3 C5 C8 125.0(4)
C3 C5 S1 126.2(3)
C8 C5 S1 108.8(3)
C10 C6 C4 120.2(4)
C11 C7 C1 122.5(4)
C6 C10 C11 120.9(4)
C7 C11 C10 119.4(5)
C4 S1 C5 104.27(15)
C13 Si1 C9 110.9(2)
C13 Si1 C12 106.8(3)
C9 Si1 C12 105.0(3)
C13 Si1 C3 108.91(19)
C9 Si1 C3 109.75(16)
C12 Si1 C3 115.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.253(4)
C1 C4 1.377(4)
C1 C7 1.390(5)
C1 C2 1.459(4)
C2 C3 1.458(4)
C3 C5 1.350(5)
C3 Si1 1.889(4)
C4 C6 1.420(5)
C4 S1 1.716(4)
C5 C8 1.521(4)
C5 S1 1.730(4)
C6 C10 1.344(7)
C7 C11 1.350(5)
C9 Si1 1.853(4)
C10 C11 1.365(7)
C12 Si1 1.854(5)
C13 Si1 1.849(5)
