#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/10/2221096.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221096
loop_
_publ_author_name
'Babar, Tariq Mahmood'
'Qadeer, Ghulam'
'Rama, Nasim Hasan'
'Khawar Rauf, Muhammad'
'Wong, Wai-Yeung'
_publ_section_title
;
 3-(4-Fluorobenzyl)-1H-isochromene-1-thione
;
_journal_coeditor_code           HK2617
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o500
_journal_paper_doi               10.1107/S1600536809004152
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H11 F O S'
_chemical_formula_moiety         'C16 H11 F O S'
_chemical_formula_sum            'C16 H11 F O S'
_chemical_formula_weight         270.31
_chemical_melting_point          392(2)
_chemical_name_common            3-(4-fluorobenzyl)thioisocoumarin
_chemical_name_systematic
;
3-(4-Fluorobenzyl)-1H-isochromene-1-thione
;
_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                 95.0260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7346(6)
_cell_length_b                   17.9516(11)
_cell_length_c                   8.4481(5)
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      4.15
_cell_volume                     1319.57(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7856
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0464
_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)+(0.0856P)²+0.2983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                2655
_reflns_number_total             3188
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2617.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221096
_cod_database_fobs_code          2221096
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.07012(6) 0.65948(3) 0.36335(6) 0.0646(2) Uani d . 1 . .
O O1 0.20272(15) 0.53300(6) 0.37410(13) 0.0506(3) Uani d . 1 . .
F F1 0.51024(16) 0.13358(7) 0.29180(19) 0.0845(4) Uani d . 1 . .
C C1 0.0938(2) 0.63191(10) -0.0010(2) 0.0563(4) Uani d . 1 . .
H H1A 0.0472 0.6745 0.0350 0.068 Uiso calc R 1 . .
C C2 0.1045(3) 0.62201(12) -0.1609(2) 0.0665(5) Uani d . 1 . .
H H2A 0.0656 0.6581 -0.2326 0.080 Uiso calc R 1 . .
C C3 0.1727(3) 0.55866(12) -0.2156(2) 0.0706(6) Uani d . 1 . .
H H3A 0.1785 0.5521 -0.3241 0.085 Uiso calc R 1 . .
C C4 0.2320(3) 0.50543(11) -0.1113(2) 0.0656(5) Uani d . 1 . .
H H4A 0.2784 0.4633 -0.1496 0.079 Uiso calc R 1 . .
C C5 0.2234(2) 0.51390(9) 0.05279(18) 0.0483(4) Uani d . 1 . .
C C6 0.15271(18) 0.57814(8) 0.10781(17) 0.0439(3) Uani d . 1 . .
C C7 0.14344(18) 0.58791(9) 0.27669(18) 0.0446(3) Uani d . 1 . .
C C8 0.2707(2) 0.46929(8) 0.32005(19) 0.0482(4) Uani d . 1 . .
C C9 0.2829(2) 0.45929(9) 0.1661(2) 0.0523(4) Uani d . 1 . .
H H9A 0.3304 0.4166 0.1313 0.063 Uiso calc R 1 . .
C C10 0.3182(3) 0.41971(10) 0.4583(2) 0.0615(5) Uani d . 1 . .
H H10A 0.2320 0.4141 0.5222 0.074 Uiso calc R 1 . .
H H10B 0.4006 0.4438 0.5237 0.074 Uiso calc R 1 . .
C C11 0.3716(2) 0.34333(9) 0.4123(2) 0.0515(4) Uani d . 1 . .
C C12 0.5239(3) 0.32831(12) 0.3957(3) 0.0741(6) Uani d . 1 . .
H H12A 0.5961 0.3662 0.4129 0.089 Uiso calc R 1 . .
C C13 0.5718(2) 0.25794(14) 0.3540(3) 0.0799(7) Uani d . 1 . .
H H13A 0.6748 0.2483 0.3421 0.096 Uiso calc R 1 . .
C C14 0.4648(2) 0.20356(10) 0.3309(2) 0.0585(4) Uani d . 1 . .
C C15 0.3136(2) 0.21543(11) 0.3461(3) 0.0671(5) Uani d . 1 . .
H H15A 0.2425 0.1771 0.3292 0.081 Uiso calc R 1 . .
C C16 0.2677(2) 0.28622(11) 0.3875(3) 0.0644(5) Uani d . 1 . .
H H16A 0.1644 0.2952 0.3987 0.077 Uiso calc R 1 . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.26(18) ?
C2 C1 H1A . . 119.9 ?
C6 C1 H1A . . 119.9 ?
C1 C2 C3 . . 120.26(18) ?
C1 C2 H2A . . 119.9 ?
C3 C2 H2A . . 119.9 ?
C4 C3 C2 . . 120.55(17) ?
C4 C3 H3A . . 119.7 ?
C2 C3 H3A . . 119.7 ?
C3 C4 C5 . . 120.66(18) ?
C3 C4 H4A . . 119.7 ?
C5 C4 H4A . . 119.7 ?
C4 C5 C6 . . 118.58(15) ?
C4 C5 C9 . . 122.49(16) ?
C6 C5 C9 . . 118.92(14) ?
C1 C6 C5 . . 119.68(15) ?
C1 C6 C7 . . 121.00(15) ?
C5 C6 C7 . . 119.31(14) ?
O1 C7 C6 . . 117.29(13) ?
O1 C7 S1 . . 116.25(11) ?
C6 C7 S1 . . 126.45(12) ?
C9 C8 O1 . . 120.60(14) ?
C9 C8 C10 . . 130.03(16) ?
O1 C8 C10 . . 109.36(13) ?
C8 C9 C5 . . 120.38(15) ?
C8 C9 H9A . . 119.8 ?
C5 C9 H9A . . 119.8 ?
C8 C10 C11 . . 114.22(15) ?
C8 C10 H10A . . 108.7 ?
C11 C10 H10A . . 108.7 ?
C8 C10 H10B . . 108.7 ?
C11 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C16 C11 C12 . . 118.03(17) ?
C16 C11 C10 . . 120.16(18) ?
C12 C11 C10 . . 121.81(18) ?
C11 C12 C13 . . 121.35(19) ?
C11 C12 H12A . . 119.3 ?
C13 C12 H12A . . 119.3 ?
C14 C13 C12 . . 118.3(2) ?
C14 C13 H13A . . 120.8 ?
C12 C13 H13A . . 120.8 ?
C13 C14 C15 . . 122.61(18) ?
C13 C14 F1 . . 119.12(18) ?
C15 C14 F1 . . 118.27(18) ?
C14 C15 C16 . . 118.29(18) ?
C14 C15 H15A . . 120.9 ?
C16 C15 H15A . . 120.9 ?
C11 C16 C15 . . 121.39(18) ?
C11 C16 H16A . . 119.3 ?
C15 C16 H16A . . 119.3 ?
C7 O1 C8 . . 123.49(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.373(3) ?
C1 C6 . 1.400(2) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.382(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.370(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.403(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.406(2) ?
C5 C9 . 1.435(2) ?
C6 C7 . 1.447(2) ?
C7 O1 . 1.3573(19) ?
C7 S1 . 1.6367(16) ?
C8 C9 . 1.327(2) ?
C8 O1 . 1.3843(18) ?
C8 C10 . 1.498(2) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.510(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.373(3) ?
C11 C12 . 1.376(3) ?
C12 C13 . 1.386(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.353(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.355(3) ?
C14 F1 . 1.367(2) ?
C15 C16 . 1.387(3) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A S1 . 0.93 2.78 3.142(2) 105 yes
C3 H3A O1 1_554 0.93 2.60 3.529(2) 178 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741703
