#------------------------------------------------------------------------------
#$Date: 2016-02-10 10:06:48 +0200 (Wed, 10 Feb 2016) $
#$Revision: 176325 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/41/7224189.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_7224189
loop_
_publ_author_name
'Giofrè, Salvatore V.'
'Romeo, Roberto'
'Mancuso, Raffaella'
'Cicero, Nicola'
'Corriero, Nicola'
'Chiacchio, Ugo'
'Romeo, Giovanni'
'Gabriele, Bartolo'
_publ_section_title
;
 A new microwave-assisted thionation-heterocyclization process leading to
 benzo[c]thiophene-1(3H)-thione and 1H-isothiochromene-1-thione
 derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA01329E
_journal_year                    2016
_chemical_formula_sum            'C16 H12 O S2'
_chemical_formula_weight         284.38
_chemical_name_systematic
(Z)-3-(4-fluorobenzylidene)benzo[c]thiophene-1(3H)-thione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-14 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.920(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9659(5)
_cell_length_b                   16.3382(4)
_cell_length_c                   20.518(5)
_cell_measurement_reflns_used    126
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3.0
_cell_volume                     1328.7(4)
_computing_cell_refinement
'DIRAX (Duisenberg,1992; Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction
'EVAL (Nonius, 2002; Duisenberg et al., 2000)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1354
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26857
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         2.345
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0544
_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)+(0.0448P)²+0.5801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1719
_reflns_number_total             3085
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra01329e2.cif
_cod_data_source_block           shelx
_cod_database_code               7224189
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.0949(2) 0.03568(5) 0.17373(4) 0.0419(2) Uani 1 1 d . .
S2 S 0.0283(2) 0.17908(5) 0.25078(5) 0.0569(3) Uani 1 1 d . .
O1 O 0.3940(6) -0.25688(14) -0.03908(11) 0.0550(6) Uani 1 1 d . .
C1 C -0.1919(7) 0.02816(19) 0.29484(14) 0.0406(7) Uani 1 1 d . .
C2 C 0.0863(7) -0.11496(17) 0.11732(14) 0.0355(7) Uani 1 1 d . .
C3 C -0.0144(7) -0.06791(18) 0.17493(14) 0.0357(7) Uani 1 1 d . .
C4 C -0.0396(7) 0.07925(18) 0.24530(15) 0.0396(7) Uani 1 1 d . .
C5 C 0.2954(7) -0.20637(19) 0.00987(14) 0.0406(7) Uani 1 1 d . .
C6 C 0.0840(8) -0.20005(19) 0.11795(16) 0.0491(8) Uani 1 1 d . .
H6 H 0.0111 -0.2273 0.1547 0.059 Uiso 1 1 calc R U
C7 C -0.1695(8) -0.0992(2) 0.22673(16) 0.0422(7) Uani 1 1 d . .
H7 H -0.236(7) -0.152(2) 0.2240(15) 0.048(9) Uiso 1 1 d . .
C8 C -0.2550(7) -0.05616(19) 0.28481(14) 0.0385(7) Uani 1 1 d . .
C9 C 0.1877(9) -0.2451(2) 0.06518(16) 0.0546(9) Uani 1 1 d . .
H9 H 0.1848 -0.3020 0.0670 0.066 Uiso 1 1 calc R U
C10 C -0.4051(8) -0.1006(2) 0.33503(16) 0.0505(8) Uani 1 1 d . .
H10 H -0.4498 -0.1560 0.3289 0.061 Uiso 1 1 calc R U
C11 C 0.2958(8) -0.1227(2) 0.00741(16) 0.0493(8) Uani 1 1 d . .
H11 H 0.3648 -0.0959 -0.0299 0.059 Uiso 1 1 calc R U
C12 C -0.2779(9) 0.0638(2) 0.35413(16) 0.0523(9) Uani 1 1 d . .
H12 H -0.2373 0.1193 0.3611 0.063 Uiso 1 1 calc R U
C13 C 0.1933(8) -0.0779(2) 0.06056(16) 0.0493(8) Uani 1 1 d . .
H13 H 0.1960 -0.0211 0.0582 0.059 Uiso 1 1 calc R U
C14 C -0.4867(9) -0.0646(2) 0.39246(17) 0.0591(10) Uani 1 1 d . .
H14 H -0.5854 -0.0954 0.4248 0.071 Uiso 1 1 calc R U
C15 C 0.5327(8) -0.2205(2) -0.09518(15) 0.0524(9) Uani 1 1 d . .
H15A H 0.6036 -0.2626 -0.1243 0.079 Uiso 1 1 calc R U
H15B H 0.7231 -0.1873 -0.0822 0.079 Uiso 1 1 calc R U
H15C H 0.3649 -0.1869 -0.1169 0.079 Uiso 1 1 calc R U
C16 C -0.4216(10) 0.0181(2) 0.40234(17) 0.0627(10) Uani 1 1 d . .
H16 H -0.4751 0.0427 0.4416 0.075 Uiso 1 1 calc R U
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
C4 S1 C3 107.61(15)
C5 O1 C15 118.0(2)
C12 C1 C8 119.0(3)
C12 C1 C4 119.0(3)
C8 C1 C4 122.0(3)
C6 C2 C13 116.4(3)
C6 C2 C3 120.7(3)
C13 C2 C3 122.8(3)
C7 C3 C2 125.3(3)
C7 C3 S1 119.9(2)
C2 C3 S1 114.8(2)
C1 C4 S2 125.8(2)
C1 C4 S1 120.1(2)
S2 C4 S1 114.10(18)
O1 C5 C11 125.1(3)
O1 C5 C9 115.5(3)
C11 C5 C9 119.3(3)
C9 C6 C2 121.5(3)
C3 C7 C8 126.7(3)
C10 C8 C1 118.2(3)
C10 C8 C7 118.2(3)
C1 C8 C7 123.6(3)
C5 C9 C6 120.5(3)
C14 C10 C8 121.8(3)
C5 C11 C13 119.9(3)
C16 C12 C1 121.1(3)
C11 C13 C2 122.3(3)
C10 C14 C16 119.8(3)
C12 C16 C14 120.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.732(3)
S1 C3 1.747(3)
S2 C4 1.656(3)
O1 C5 1.367(3)
O1 C15 1.422(4)
C1 C12 1.401(4)
C1 C8 1.414(4)
C1 C4 1.462(4)
C2 C6 1.390(4)
C2 C13 1.391(4)
C2 C3 1.476(4)
C3 C7 1.347(4)
C5 C11 1.368(4)
C5 C9 1.380(4)
C6 C9 1.383(4)
C7 C8 1.434(4)
C8 C10 1.409(4)
C10 C14 1.365(4)
C11 C13 1.386(4)
C12 C16 1.378(5)
C14 C16 1.390(5)
