#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/28/7102847.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_7102847
loop_
_publ_author_name
'Granados, Alejandro M'
'Fracaroli, Alejandro M'
'de Rossi, Rita H'
'Fuertes, Pedro'
'Torroba, Tomás'
_publ_section_title
;
 Alkynyl Fischer carbene complex as a traceless directing group for the
 regioselective cycloaddition of dithiolethiones to arylacetylene:
 synthesis of E-dithiafulvene thione and dithioesters.
;
_journal_issue                   4
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              483
_journal_page_last               485
_journal_paper_doi               10.1039/b715857b
_journal_year                    2008
_chemical_formula_moiety         'C16 H16 S4'
_chemical_formula_sum            'C16 H16 S4'
_chemical_formula_weight         336.53
_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                 98.52(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.354(6)
_cell_length_b                   11.400(3)
_cell_length_c                   8.9237(17)
_cell_measurement_reflns_used    3086
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.23
_cell_volume                     1544.8(8)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14425
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0372
_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)+(0.0398P)²+0.2986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                2280
_reflns_number_total             2717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715857b.txt
_cod_data_source_block           3
_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_H-M      P2(1)/c
_cod_database_code               7102847
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
S1 S 0.93683(4) 0.02989(5) 0.33411(7) 0.02810(18) Uani 1 1 d . . .
S2 S 0.95725(4) 0.21083(5) 0.11241(7) 0.02831(18) Uani 1 1 d . . .
S3 S 0.76749(4) 0.04786(5) 0.45706(7) 0.03121(18) Uani 1 1 d . . .
S4 S 0.64638(4) 0.22850(5) 0.28983(8) 0.03341(19) Uani 1 1 d . . .
C1 C 1.03154(16) 0.0276(2) 0.2487(3) 0.0291(6) Uani 1 1 d . . .
H1 H 1.0747 -0.0315 0.2747 0.035 Uiso 1 1 calc R . .
C2 C 1.04331(15) 0.10923(19) 0.1466(3) 0.0243(5) Uani 1 1 d . . .
C3 C 1.11886(15) 0.1214(2) 0.0640(2) 0.0247(5) Uani 1 1 d . . .
C4 C 1.17771(15) 0.0283(2) 0.0593(3) 0.0272(6) Uani 1 1 d . . .
H4 H 1.1688 -0.0429 0.1102 0.033 Uiso 1 1 calc R . .
C5 C 1.24835(16) 0.0386(2) -0.0184(3) 0.0316(6) Uani 1 1 d . . .
H5 H 1.2879 -0.0253 -0.0205 0.038 Uiso 1 1 calc R . .
C6 C 1.26191(16) 0.1418(2) -0.0935(3) 0.0322(6) Uani 1 1 d . . .
H6 H 1.3102 0.1483 -0.1483 0.039 Uiso 1 1 calc R . .
C7 C 1.20538(16) 0.2347(2) -0.0887(3) 0.0332(6) Uani 1 1 d . . .
H7 H 1.2152 0.3060 -0.1387 0.040 Uiso 1 1 calc R . .
C8 C 1.13406(16) 0.2245(2) -0.0110(3) 0.0310(6) Uani 1 1 d . . .
H8 H 1.0950 0.2889 -0.0089 0.037 Uiso 1 1 calc R . .
C9 C 0.89200(15) 0.15239(19) 0.2367(3) 0.0243(5) Uani 1 1 d . . .
C10 C 0.81079(15) 0.2001(2) 0.2448(3) 0.0267(5) Uani 1 1 d . . .
H10 H 0.7951 0.2687 0.1865 0.032 Uiso 1 1 calc R . .
C11 C 0.74842(15) 0.15625(19) 0.3321(3) 0.0247(5) Uani 1 1 d . . .
C12 C 0.57108(15) 0.1412(2) 0.3820(3) 0.0274(6) Uani 1 1 d . . .
H12 H 0.5960 0.1274 0.4906 0.033 Uiso 1 1 calc R . .
C13 C 0.54825(16) 0.0240(2) 0.3007(3) 0.0317(6) Uani 1 1 d . . .
H13A H 0.5965 -0.0017 0.2460 0.038 Uiso 1 1 calc R . .
H13B H 0.5376 -0.0378 0.3739 0.038 Uiso 1 1 calc R . .
C14 C 0.46559(17) 0.0486(2) 0.1911(3) 0.0347(6) Uani 1 1 d . . .
H14A H 0.4324 -0.0245 0.1627 0.042 Uiso 1 1 calc R . .
H14B H 0.4795 0.0872 0.0981 0.042 Uiso 1 1 calc R . .
C15 C 0.41372(17) 0.1304(2) 0.2803(3) 0.0389(7) Uani 1 1 d . . .
H15A H 0.3713 0.1779 0.2110 0.047 Uiso 1 1 calc R . .
H15B H 0.3811 0.0853 0.3488 0.047 Uiso 1 1 calc R . .
C16 C 0.48311(16) 0.2084(2) 0.3705(3) 0.0330(6) Uani 1 1 d . . .
H16A H 0.4680 0.2238 0.4727 0.040 Uiso 1 1 calc R . .
H16B H 0.4872 0.2843 0.3181 0.040 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'
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
C9 S1 C1 95.05(11) . . ?
C9 S2 C2 97.31(11) . . ?
C11 S4 C12 104.66(11) . . ?
C2 C1 S1 119.73(19) . . ?
C2 C1 H1 120.1 . . ?
S1 C1 H1 120.1 . . ?
C1 C2 C3 127.3(2) . . ?
C1 C2 S2 113.94(18) . . ?
C3 C2 S2 118.79(17) . . ?
C8 C3 C4 118.2(2) . . ?
C8 C3 C2 121.5(2) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C10 C9 S1 126.15(18) . . ?
C10 C9 S2 119.79(18) . . ?
S1 C9 S2 113.98(13) . . ?
C9 C10 C11 125.7(2) . . ?
C9 C10 H10 117.1 . . ?
C11 C10 H10 117.1 . . ?
C10 C11 S3 124.56(18) . . ?
C10 C11 S4 111.74(17) . . ?
S3 C11 S4 123.69(14) . . ?
C13 C12 C16 105.31(19) . . ?
C13 C12 S4 112.30(16) . . ?
C16 C12 S4 107.95(16) . . ?
C13 C12 H12 110.4 . . ?
C16 C12 H12 110.4 . . ?
S4 C12 H12 110.4 . . ?
C14 C13 C12 104.79(19) . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
C13 C14 C15 103.3(2) . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C16 C15 C14 104.7(2) . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 C12 106.43(19) . . ?
C15 C16 H16A 110.4 . . ?
C12 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C12 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
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
S1 C9 1.733(2) . ?
S1 C1 1.739(3) . ?
S2 C9 1.734(2) . ?
S2 C2 1.750(2) . ?
S3 C11 1.661(2) . ?
S4 C11 1.761(2) . ?
S4 C12 1.813(2) . ?
C1 C2 1.333(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.470(3) . ?
C3 C8 1.389(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.374(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.372(3) . ?
C10 C11 1.413(3) . ?
C10 H10 0.9500 . ?
C12 C13 1.537(3) . ?
C12 C16 1.543(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.509(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
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
C9 S1 C1 C2 0.4(2) . . . . ?
S1 C1 C2 C3 179.65(18) . . . . ?
S1 C1 C2 S2 -0.1(3) . . . . ?
C9 S2 C2 C1 -0.3(2) . . . . ?
C9 S2 C2 C3 179.96(17) . . . . ?
C1 C2 C3 C8 -164.1(2) . . . . ?
S2 C2 C3 C8 15.6(3) . . . . ?
C1 C2 C3 C4 15.9(4) . . . . ?
S2 C2 C3 C4 -164.37(17) . . . . ?
C8 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C5 179.6(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C3 0.6(4) . . . . ?
C4 C3 C8 C7 0.2(4) . . . . ?
C2 C3 C8 C7 -179.8(2) . . . . ?
C1 S1 C9 C10 176.0(2) . . . . ?
C1 S1 C9 S2 -0.57(15) . . . . ?
C2 S2 C9 C10 -176.24(19) . . . . ?
C2 S2 C9 S1 0.53(15) . . . . ?
S1 C9 C10 C11 -1.3(4) . . . . ?
S2 C9 C10 C11 175.04(18) . . . . ?
C9 C10 C11 S3 7.8(4) . . . . ?
C9 C10 C11 S4 -170.9(2) . . . . ?
C12 S4 C11 C10 168.66(16) . . . . ?
C12 S4 C11 S3 -10.10(18) . . . . ?
C11 S4 C12 C13 -72.56(19) . . . . ?
C11 S4 C12 C16 171.79(16) . . . . ?
C16 C12 C13 C14 24.8(2) . . . . ?
S4 C12 C13 C14 -92.5(2) . . . . ?
C12 C13 C14 C15 -38.4(3) . . . . ?
C13 C14 C15 C16 37.4(3) . . . . ?
C14 C15 C16 C12 -21.9(3) . . . . ?
C13 C12 C16 C15 -1.6(3) . . . . ?
S4 C12 C16 C15 118.60(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653024
