#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/01/7200164.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_7200164
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 H16 O S'
_chemical_formula_sum            'C15 H16 O S'
_chemical_formula_weight         244.35
_chemical_name_common            3-Cyclohexyl-1H-isochromene-1-thione
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             'Aug 08 00:02:31 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record
;
;
_cell_angle_alpha                90
_cell_angle_beta                 105.704(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9463(14)
_cell_length_b                   12.335(2)
_cell_length_c                   12.338(2)
_cell_measurement_reflns_used    1537
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.36
_cell_volume                     1310.7(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10010
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_correction_T_min  0.9161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0454
_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)+(0.0515P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                1640
_reflns_number_total             2570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B807896c.txt
_cod_data_source_block           chsic_m
_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 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.
 
 Antanas Vaitkus,
 2019-09-17
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7200164
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01784(8) 0.53284(6) 0.29523(6) 0.0873(3) Uani 1 1 d . . .
O1 O 0.15208(15) 0.40566(11) 0.18893(10) 0.0591(4) Uani 1 1 d . . .
C1 C 0.1084(2) 0.50996(17) 0.19872(18) 0.0601(6) Uani 1 1 d . . .
C2 C 0.2237(2) 0.37076(16) 0.10901(15) 0.0508(5) Uani 1 1 d . . .
C3 C 0.2524(2) 0.44076(18) 0.03538(17) 0.0596(6) Uani 1 1 d D . .
C4 C 0.2485(3) 0.6294(2) -0.0352(2) 0.0827(8) Uani 1 1 d D . .
C5 C 0.2159(4) 0.7367(3) -0.0249(3) 0.1026(10) Uani 1 1 d D . .
C6 C 0.1482(4) 0.7714(2) 0.0574(3) 0.1024(10) Uani 1 1 d D . .
C7 C 0.1123(3) 0.6991(2) 0.1312(3) 0.0827(7) Uani 1 1 d D . .
C8 C 0.1454(2) 0.58805(17) 0.12258(17) 0.0619(6) Uani 1 1 d . . .
C9 C 0.2153(2) 0.55305(18) 0.03960(18) 0.0629(6) Uani 1 1 d . . .
C10 C 0.2603(2) 0.25314(15) 0.12480(14) 0.0500(5) Uani 1 1 d D . .
C11 C 0.3846(3) 0.23255(19) 0.23504(16) 0.0656(6) Uani 1 1 d D . .
C12 C 0.4129(3) 0.1122(2) 0.25559(19) 0.0727(7) Uani 1 1 d D . .
C13 C 0.4587(3) 0.0590(2) 0.1584(2) 0.0809(7) Uani 1 1 d D . .
C14 C 0.3363(3) 0.0800(2) 0.0484(2) 0.0789(7) Uani 1 1 d D . .
C15 C 0.3072(3) 0.20096(18) 0.02750(17) 0.0625(6) Uani 1 1 d D . .
H3 H 0.303(2) 0.4143(15) -0.0239(14) 0.064(6) Uiso 1 1 d D . .
H4 H 0.297(3) 0.6032(19) -0.0978(17) 0.099(8) Uiso 1 1 d D . .
H5 H 0.241(3) 0.7948(19) -0.079(2) 0.125(9) Uiso 1 1 d D . .
H6 H 0.119(3) 0.8511(16) 0.063(2) 0.143(11) Uiso 1 1 d D . .
H7 H 0.066(2) 0.7201(18) 0.1944(16) 0.087(8) Uiso 1 1 d D . .
H10 H 0.1578(19) 0.2157(14) 0.1292(14) 0.065(5) Uiso 1 1 d D . .
H11A H 0.489(2) 0.2720(18) 0.2288(19) 0.096(8) Uiso 1 1 d D . .
H11B H 0.353(2) 0.2727(16) 0.2986(16) 0.088(7) Uiso 1 1 d D . .
H12A H 0.497(2) 0.097(2) 0.3315(16) 0.105(8) Uiso 1 1 d D . .
H12B H 0.309(2) 0.0744(16) 0.2628(17) 0.082(7) Uiso 1 1 d D . .
H13A H 0.475(3) -0.0233(14) 0.172(2) 0.100(8) Uiso 1 1 d D . .
H13B H 0.567(2) 0.0950(18) 0.1561(19) 0.097(8) Uiso 1 1 d D . .
H14A H 0.230(2) 0.042(2) 0.048(2) 0.128(11) Uiso 1 1 d D . .
H14B H 0.372(2) 0.0513(17) -0.0201(16) 0.090(7) Uiso 1 1 d D . .
H15A H 0.4067(19) 0.2407(14) 0.0233(15) 0.064(6) Uiso 1 1 d D . .
H15B H 0.2237(19) 0.2171(15) -0.0468(14) 0.071(6) 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
O1 C1 C8 116.84(18) . . ?
O1 C1 S1 116.02(16) . . ?
O1 C2 C10 109.77(15) . . ?
C1 O1 C2 123.92(16) . . ?
C2 C3 C9 121.0(2) . . ?
C2 C10 C15 114.07(16) . . ?
C2 C10 C11 111.09(16) . . ?
C2 C10 H10 105.9(10) . . ?
C2 C3 H3 119.5(11) . . ?
C3 C2 O1 119.91(19) . . ?
C3 C2 C10 130.30(18) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C9 C3 122.2(2) . . ?
C4 C5 H5 121.2(16) . . ?
C5 C4 C9 120.0(3) . . ?
C5 C4 H4 120.9(14) . . ?
C5 C6 H6 121.3(17) . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7 124.2(13) . . ?
C6 C5 H5 117.9(16) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 117.8(17) . . ?
C7 C8 C1 120.6(2) . . ?
C8 C9 C4 119.2(2) . . ?
C8 C9 C3 118.6(2) . . ?
C8 C1 S1 127.14(17) . . ?
C8 C7 H7 116.4(13) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C3 H3 119.5(11) . . ?
C9 C4 H4 119.1(14) . . ?
C9 C8 C1 119.63(19) . . ?
C10 C11 H11A 107.4(12) . . ?
C10 C11 H11B 108.4(12) . . ?
C10 C15 H15B 109.4(10) . . ?
C10 C15 C14 110.63(18) . . ?
C10 C15 H15A 105.4(10) . . ?
C11 C12 C13 111.1(2) . . ?
C11 C10 H10 108.6(10) . . ?
C11 C12 H12A 111.7(14) . . ?
C11 C12 H12B 109.5(11) . . ?
C12 C11 C10 111.11(18) . . ?
C12 C11 H11A 110.2(13) . . ?
C12 C11 H11B 114.3(12) . . ?
C12 C13 H13A 110.5(14) . . ?
C12 C13 H13B 106.3(13) . . ?
C13 C14 C15 111.6(2) . . ?
C13 C14 H14A 110.8(16) . . ?
C13 C14 H14B 111.0(12) . . ?
C13 C12 H12A 110.5(13) . . ?
C13 C12 H12B 107.7(12) . . ?
C14 C13 C12 110.4(2) . . ?
C14 C13 H13A 110.5(14) . . ?
C14 C15 H15A 111.4(10) . . ?
C14 C13 H13B 110.1(13) . . ?
C14 C15 H15B 112.9(11) . . ?
C15 C14 H14B 105.7(12) . . ?
C15 C10 H10 106.8(10) . . ?
C15 C14 H14A 108.7(16) . . ?
C15 C10 C11 110.06(16) . . ?
H11A C11 H11B 105.0(17) . . ?
H12A C12 H12B 106.1(18) . . ?
H13A C13 H13B 108.8(19) . . ?
H14A C14 H14B 109(2) . . ?
H15A C15 H15B 106.9(15) . . ?
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 C1 1.636(2) . ?
O1 C1 1.359(2) . ?
O1 C2 1.382(2) . ?
C1 C8 1.445(3) . ?
C2 C3 1.328(3) . ?
C2 C10 1.489(3) . ?
C3 C9 1.429(3) . ?
C3 H3 1.014(14) . ?
C4 C5 1.369(4) . ?
C4 C9 1.405(3) . ?
C4 H4 1.036(16) . ?
C5 C6 1.384(4) . ?
C5 H5 1.042(17) . ?
C6 C7 1.373(4) . ?
C6 H6 1.024(18) . ?
C7 C8 1.411(3) . ?
C7 H7 1.013(15) . ?
C8 C9 1.404(3) . ?
C10 C15 1.518(2) . ?
C10 C11 1.527(3) . ?
C10 H10 1.041(14) . ?
C11 C12 1.516(3) . ?
C11 H11A 1.077(16) . ?
C11 H11B 1.028(15) . ?
C12 C13 1.518(3) . ?
C12 H12A 1.045(16) . ?
C12 H12B 1.065(16) . ?
C13 C14 1.518(3) . ?
C13 H13A 1.033(16) . ?
C13 H13B 1.075(16) . ?
C14 C15 1.524(3) . ?
C14 H14A 1.063(17) . ?
C14 H14B 1.045(16) . ?
C15 H15A 1.030(14) . ?
C15 H15B 1.033(15) . ?
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
S1 C1 C8 C7 4.3(3) . . . . ?
S1 C1 C8 C9 -175.91(15) . . . . ?
O1 C1 C8 C9 3.4(3) . . . . ?
O1 C1 C8 C7 -176.33(17) . . . . ?
O1 C2 C10 C15 167.60(16) . . . . ?
O1 C2 C10 C11 -67.3(2) . . . . ?
O1 C2 C3 C9 2.2(3) . . . . ?
C1 O1 C2 C3 -0.5(3) . . . . ?
C1 O1 C2 C10 177.99(15) . . . . ?
C1 C8 C9 C4 179.01(18) . . . . ?
C1 C8 C9 C3 -2.0(3) . . . . ?
C2 C3 C9 C8 -0.9(3) . . . . ?
C2 C3 C9 C4 178.1(2) . . . . ?
C2 C10 C11 C12 175.57(18) . . . . ?
C2 O1 C1 C8 -2.3(2) . . . . ?
C2 C10 C15 C14 -177.77(18) . . . . ?
C2 O1 C1 S1 177.16(13) . . . . ?
C3 C2 C10 C15 -14.1(3) . . . . ?
C3 C2 C10 C11 111.0(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C4 C9 C8 1.5(3) . . . . ?
C5 C4 C9 C3 -177.6(2) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C6 C7 C8 C1 -179.8(2) . . . . ?
C7 C8 C9 C4 -1.2(3) . . . . ?
C7 C8 C9 C3 177.81(18) . . . . ?
C9 C4 C5 C6 -0.9(4) . . . . ?
C10 C2 C3 C9 -176.01(18) . . . . ?
C10 C11 C12 C13 57.0(3) . . . . ?
C11 C10 C15 C14 56.6(2) . . . . ?
C11 C12 C13 C14 -55.9(3) . . . . ?
C12 C13 C14 C15 55.9(3) . . . . ?
C13 C14 C15 C10 -56.8(3) . . . . ?
C15 C10 C11 C12 -57.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25940748
2 PubChem 46242069
