#------------------------------------------------------------------------------
#$Date: 2019-09-17 19:47:23 +0300 (Tue, 17 Sep 2019) $
#$Revision: 218400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/55/7215519.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_7215519
loop_
_publ_author_name
'Hathwar, Venkatesha R.'
'Manivel, P.'
'Nawaz Khan, F.'
'Guru Row, T. N.'
_publ_section_title
;
 Evaluation of intermolecular interactions in thioisocoumarin derivatives:
 the role of the sulfur atom in generating packing motifs
;
_journal_coden_ASTM              CRECF4
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              284
_journal_page_last               291
_journal_paper_doi               10.1039/b807896c
_journal_volume                  11
_journal_year                    2009
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C15 H10 O S'
_chemical_formula_sum            'C15 H10 O S'
_chemical_formula_weight         238.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             'Aug 07 22:53:33 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record
;
;
_cell_angle_alpha                90
_cell_angle_beta                 92.701(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8992(5)
_cell_length_b                   15.2947(18)
_cell_length_c                   19.007(2)
_cell_measurement_reflns_used    958
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      24.18
_cell_measurement_theta_min      1.73
_cell_volume                     1132.3(2)
_computing_cell_refinement       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_collection       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker, 2000)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7940
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0752
_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)+(0.0548P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                1301
_reflns_number_total             1998
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7200168
_cod_data_source_file            b807896c.txt
_cod_data_source_block           vh4_m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/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 2281 2013-09-26 08:29:07Z andrius 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-17

 Marked entry as a duplicate of entry 7200168.

 Antanas Vaitkus,
 2019-09-17
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7215519
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
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 0.0978(3) -0.14695(7) 0.79040(6) 0.0592(4) Uani 1 1 d .
O1 O 0.1255(6) 0.01126(15) 0.83289(12) 0.0436(7) Uani 1 1 d .
C1 C 0.0167(9) -0.0430(2) 0.77922(18) 0.0394(9) Uani 1 1 d .
C2 C 0.0867(9) 0.1014(2) 0.83110(18) 0.0363(9) Uani 1 1 d .
C3 C -0.0619(9) 0.1400(2) 0.77465(18) 0.0396(9) Uani 1 1 d D
C4 C -0.3482(10) 0.1281(3) 0.6559(2) 0.0480(11) Uani 1 1 d D
C5 C -0.4711(10) 0.0772(3) 0.6006(2) 0.0520(11) Uani 1 1 d D
C6 C -0.4406(10) -0.0129(3) 0.6038(2) 0.0532(11) Uani 1 1 d D
C7 C -0.2841(10) -0.0528(3) 0.6618(2) 0.0485(11) Uani 1 1 d D
C8 C -0.1531(9) -0.0016(2) 0.71811(18) 0.0375(9) Uani 1 1 d .
C9 C -0.1894(9) 0.0892(2) 0.71545(18) 0.0360(9) Uani 1 1 d .
C10 C 0.2211(8) 0.1419(2) 0.89684(18) 0.0372(9) Uani 1 1 d .
C11 C 0.2591(11) 0.0939(3) 0.9587(2) 0.0499(11) Uani 1 1 d D
C12 C 0.3819(11) 0.1329(3) 1.0208(2) 0.0581(12) Uani 1 1 d D
C13 C 0.4731(11) 0.2192(3) 1.0209(2) 0.0556(12) Uani 1 1 d D
C14 C 0.4381(10) 0.2676(3) 0.9600(2) 0.0558(11) Uani 1 1 d D
C15 C 0.3127(10) 0.2295(3) 0.8980(2) 0.0476(10) Uani 1 1 d D
H3 H -0.100(8) 0.2074(13) 0.7718(18) 0.049(10) Uiso 1 1 d D
H4 H -0.370(9) 0.1964(13) 0.652(2) 0.061(12) Uiso 1 1 d D
H5 H -0.595(9) 0.105(2) 0.5559(15) 0.081(14) Uiso 1 1 d D
H6 H -0.535(9) -0.054(2) 0.5645(15) 0.058(11) Uiso 1 1 d D
H7 H -0.271(9) -0.1197(13) 0.6647(19) 0.054(11) Uiso 1 1 d D
H11 H 0.196(9) 0.0274(14) 0.956(2) 0.071(13) Uiso 1 1 d D
H12 H 0.417(10) 0.089(2) 1.0631(17) 0.087(15) Uiso 1 1 d D
H13 H 0.582(8) 0.249(2) 1.0655(14) 0.067(12) Uiso 1 1 d D
H14 H 0.513(8) 0.3330(14) 0.9608(19) 0.060(11) Uiso 1 1 d D
H15 H 0.309(8) 0.266(2) 0.8509(13) 0.057(11) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
O1 C1 C8 116.4(3)
O1 C2 C10 111.4(3)
O1 C1 S1 116.3(2)
C1 O1 C2 123.7(3)
C2 C3 C9 120.8(3)
C2 C3 H3 122.4(19)
C3 C2 O1 120.2(3)
C3 C2 C10 128.4(3)
C4 C5 C6 120.3(4)
C4 C5 H5 121(2)
C4 C9 C8 119.5(3)
C4 C9 C3 121.9(3)
C5 C4 C9 120.2(4)
C5 C4 H4 119(2)
C5 C6 H6 124(2)
C6 C7 C8 119.7(4)
C6 C7 H7 120(2)
C6 C5 H5 118(2)
C7 C6 C5 120.6(4)
C7 C6 H6 116(2)
C7 C8 C1 120.2(3)
C8 C1 S1 127.3(3)
C8 C9 C3 118.6(3)
C8 C7 H7 120(2)
C9 C3 H3 116.8(19)
C9 C4 H4 121(2)
C9 C8 C7 119.6(3)
C9 C8 C1 120.2(3)
C10 C11 C12 120.7(4)
C10 C15 H15 120(2)
C10 C11 H11 117(2)
C11 C10 C2 121.1(3)
C11 C12 H12 114(2)
C12 C13 C14 120.2(4)
C12 C13 H13 122(2)
C12 C11 H11 122(2)
C13 C12 C11 119.8(4)
C13 C14 C15 120.5(4)
C13 C14 H14 119(2)
C13 C12 H12 126(2)
C14 C13 H13 118(2)
C14 C15 C10 120.0(4)
C14 C15 H15 120(2)
C15 C14 H14 120(2)
C15 C10 C11 118.8(3)
C15 C10 C2 120.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.633(4)
O1 C1 1.367(4)
O1 C2 1.387(4)
C1 C8 1.455(5)
C2 C3 1.333(5)
C2 C10 1.469(5)
C3 C9 1.437(5)
C3 H3 1.043(18)
C4 C5 1.376(5)
C4 C9 1.397(5)
C4 H4 1.050(18)
C5 C6 1.383(6)
C5 H5 1.049(19)
C6 C7 1.377(5)
C6 H6 1.034(18)
C7 C8 1.403(5)
C7 H7 1.026(18)
C8 C9 1.397(5)
C10 C15 1.387(5)
C10 C11 1.388(5)
C11 C12 1.388(5)
C11 H11 1.047(19)
C12 C13 1.367(6)
C12 H12 1.051(19)
C13 C14 1.376(6)
C13 H13 1.039(19)
C14 C15 1.383(5)
C14 H14 1.042(19)
C15 H15 1.051(18)
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
S1 C1 C8 C9 -177.1(3)
S1 C1 C8 C7 3.5(5)
O1 C1 C8 C9 1.8(5)
O1 C1 C8 C7 -177.6(3)
O1 C2 C10 C15 158.5(3)
O1 C2 C10 C11 -21.5(5)
O1 C2 C3 C9 1.1(5)
C1 C8 C9 C4 179.0(3)
C1 O1 C2 C3 -0.4(5)
C1 O1 C2 C10 178.7(3)
C1 C8 C9 C3 -1.2(5)
C2 C3 C9 C4 179.5(4)
C2 C3 C9 C8 -0.3(5)
C2 C10 C11 C12 -179.1(4)
C2 O1 C1 C8 -1.0(5)
C2 O1 C1 S1 178.0(2)
C2 C10 C15 C14 179.8(4)
C3 C2 C10 C15 -22.5(6)
C3 C2 C10 C11 157.6(4)
C4 C5 C6 C7 -0.6(7)
C5 C6 C7 C8 -0.3(6)
C5 C4 C9 C8 0.7(6)
C5 C4 C9 C3 -179.1(4)
C6 C7 C8 C9 1.4(6)
C6 C7 C8 C1 -179.2(4)
C7 C8 C9 C4 -1.6(5)
C7 C8 C9 C3 178.2(3)
C9 C4 C5 C6 0.4(6)
C10 C2 C3 C9 -177.9(3)
C10 C11 C12 C13 -1.3(7)
C11 C12 C13 C14 1.0(7)
C11 C10 C15 C14 -0.2(6)
C12 C13 C14 C15 -0.4(7)
C13 C14 C15 C10 0.0(6)
C15 C10 C11 C12 0.9(6)
