#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158116.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_7158116
loop_
_publ_author_name
'Mondal, Santa'
'Yashmin, Sabina'
'Ali, Rashid'
'Soundaram, R.'
'Ghosh, Siddhartha S.'
'Khan, Abu Taleb'
_publ_section_title
;
 Synthesis of biologically active fused 1,4-oxathiin derivatives from
 4-hydroxydithiocoumarins, arylacetylenes and dimethyl sulfoxide by
 Cu(i)-catalyzed C-H functionalization and cross-dehydrogenative C-S
 coupling reactions.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5818
_journal_page_last               5826
_journal_paper_doi               10.1039/d1ob00846c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C17 H9 F O2 S2'
_chemical_formula_weight         428.36
_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'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc26t2ns
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-12-12 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.360(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.147(2)
_cell_length_b                   5.4814(8)
_cell_length_c                   18.975(3)
_cell_measurement_reflns_used    8296
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.28
_cell_volume                     1388.2(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.034
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         1.572
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       Needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.648
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.648
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0632
_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)+(0.1000P)²+0.3767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2129
_refine_ls_wR_factor_ref         0.2360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1955
_reflns_number_total             2456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00846c2.cif
_cod_data_source_block           SM-12E-19_0ma_a
_cod_depositor_comments
;
          Adding full bibliography for 7158116.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H36 F4 O8 S8'
_cod_original_formula_weight         1313.45
_cod_original_formula_units_Z            1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158116
_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.
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.56587(10) 0.7550(2) 0.06429(7) 0.0503(4) Uani 1 1 d . . . . .
S002 S 0.37677(10) 0.8611(2) 0.08932(7) 0.0548(5) Uani 1 1 d . . . . .
O003 O 0.4257(2) 0.4496(5) 0.19381(18) 0.0463(8) Uani 1 1 d . . . . .
F1 F 0.8970(3) 0.4261(7) 0.0677(2) 0.0833(11) Uani 1 1 d . . . . .
O005 O 0.5905(3) 0.1766(7) 0.2323(2) 0.0683(12) Uani 1 1 d . . . . .
C006 C 0.4975(3) 0.4929(7) 0.1595(2) 0.0372(10) Uani 1 1 d . . . . .
C007 C 0.3839(3) 0.6213(7) 0.2954(2) 0.0388(10) Uani 1 1 d . . . . .
C008 C 0.6609(3) 0.5401(8) 0.0968(2) 0.0401(10) Uani 1 1 d . . . . .
C009 C 0.6625(3) 0.3572(8) 0.1486(2) 0.0393(10) Uani 1 1 d . . . . .
C00A C 0.3903(3) 0.6554(7) 0.2205(3) 0.0396(10) Uani 1 1 d . . . . .
C00B C 0.5836(4) 0.3295(8) 0.1837(3) 0.0427(11) Uani 1 1 d . . . . .
C00C C 0.4831(4) 0.6751(8) 0.1096(2) 0.0420(11) Uani 1 1 d . . . . .
C00D C 0.3364(4) 0.7932(8) 0.3262(3) 0.0461(11) Uani 1 1 d . . . . .
H00D H 0.3086 0.9314 0.2988 0.055 Uiso 1 1 calc R U . . .
C00E C 0.4241(3) 0.4130(8) 0.3373(3) 0.0452(11) Uani 1 1 d . . . . .
H00E H 0.4556 0.2943 0.3180 0.054 Uiso 1 1 calc R U . . .
C00F C 0.3298(4) 0.7624(9) 0.3967(3) 0.0524(13) Uani 1 1 d . . . . .
H00F H 0.2980 0.8793 0.4164 0.063 Uiso 1 1 calc R U . . .
C00G C 0.3657(4) 0.8521(8) 0.1785(2) 0.0453(11) Uani 1 1 d . . . . .
H00G H 0.3421 0.9886 0.1966 0.054 Uiso 1 1 calc R U . . .
C00H C 0.4163(4) 0.3849(9) 0.4081(3) 0.0532(13) Uani 1 1 d . . . . .
H00H H 0.4427 0.2461 0.4358 0.064 Uiso 1 1 calc R U . . .
C00I C 0.7426(4) 0.1954(9) 0.1694(3) 0.0505(12) Uani 1 1 d . . . . .
H00I H 0.7430 0.0703 0.2026 0.061 Uiso 1 1 calc R U . . .
C00J C 0.7407(4) 0.5623(9) 0.0690(3) 0.0517(12) Uani 1 1 d . . . . .
H00J H 0.7405 0.6835 0.0347 0.062 Uiso 1 1 calc R U . . .
C00K C 0.3706(4) 0.5579(10) 0.4376(3) 0.0524(13) Uani 1 1 d . . . . .
H00K H 0.3670 0.5373 0.4853 0.063 Uiso 1 1 calc R U . . .
C00L C 0.8182(4) 0.4036(10) 0.0932(3) 0.0540(13) Uani 1 1 d . . . . .
C00M C 0.8205(4) 0.2146(10) 0.1426(3) 0.0578(14) Uani 1 1 d . . . . .
H00M H 0.8735 0.1047 0.1569 0.069 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C S001 C008 103.0(2) . . ?
C00C S002 C00G 96.7(2) . . ?
C00A O003 C006 115.8(3) . . ?
C00C C006 O003 119.4(4) . . ?
C00C C006 C00B 126.4(4) . . ?
O003 C006 C00B 114.2(4) . . ?
C00D C007 C00E 118.3(4) . . ?
C00D C007 C00A 121.0(4) . . ?
C00E C007 C00A 120.7(4) . . ?
C009 C008 C00J 119.9(4) . . ?
C009 C008 S001 124.4(4) . . ?
C00J C008 S001 115.6(4) . . ?
C00I C009 C008 118.6(4) . . ?
C00I C009 C00B 118.1(4) . . ?
C008 C009 C00B 123.3(4) . . ?
C00G C00A O003 119.8(4) . . ?
C00G C00A C007 127.0(4) . . ?
O003 C00A C007 113.2(4) . . ?
O005 C00B C006 120.4(4) . . ?
O005 C00B C009 121.6(4) . . ?
C006 C00B C009 118.0(4) . . ?
C006 C00C S001 124.8(4) . . ?
C006 C00C S002 120.4(4) . . ?
S001 C00C S002 114.8(3) . . ?
C00F C00D C007 121.4(4) . . ?
C00F C00D H00D 119.3 . . ?
C007 C00D H00D 119.3 . . ?
C00H C00E C007 119.4(4) . . ?
C00H C00E H00E 120.3 . . ?
C007 C00E H00E 120.3 . . ?
C00K C00F C00D 119.7(5) . . ?
C00K C00F H00F 120.2 . . ?
C00D C00F H00F 120.2 . . ?
C00A C00G S002 121.1(4) . . ?
C00A C00G H00G 119.4 . . ?
S002 C00G H00G 119.4 . . ?
C00K C00H C00E 121.1(5) . . ?
C00K C00H H00H 119.4 . . ?
C00E C00H H00H 119.4 . . ?
C00M C00I C009 122.0(5) . . ?
C00M C00I H00I 119.0 . . ?
C009 C00I H00I 119.0 . . ?
C00L C00J C008 118.7(5) . . ?
C00L C00J H00J 120.7 . . ?
C008 C00J H00J 120.7 . . ?
C00H C00K C00F 120.1(5) . . ?
C00H C00K H00K 120.0 . . ?
C00F C00K H00K 120.0 . . ?
C00J C00L F1 119.2(5) . . ?
C00J C00L C00M 122.8(5) . . ?
F1 C00L C00M 117.9(5) . . ?
C00I C00M C00L 117.9(5) . . ?
C00I C00M H00M 121.0 . . ?
C00L C00M H00M 121.0 . . ?
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
S001 C00C 1.723(5) . ?
S001 C008 1.739(5) . ?
S002 C00C 1.751(5) . ?
S002 C00G 1.751(5) . ?
O003 C00A 1.396(5) . ?
O003 C006 1.397(5) . ?
F1 C00L 1.360(6) . ?
O005 C00B 1.226(5) . ?
C006 C00C 1.344(6) . ?
C006 C00B 1.459(6) . ?
C007 C00D 1.393(6) . ?
C007 C00E 1.400(6) . ?
C007 C00A 1.466(6) . ?
C008 C009 1.399(6) . ?
C008 C00J 1.400(6) . ?
C009 C00I 1.389(6) . ?
C009 C00B 1.484(6) . ?
C00A C00G 1.317(6) . ?
C00D C00F 1.381(6) . ?
C00D H00D 0.9300 . ?
C00E C00H 1.392(7) . ?
C00E H00E 0.9300 . ?
C00F C00K 1.376(7) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H C00K 1.368(7) . ?
C00H H00H 0.9300 . ?
C00I C00M 1.362(7) . ?
C00I H00I 0.9300 . ?
C00J C00L 1.354(7) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00M 1.390(8) . ?
C00M H00M 0.9300 . ?
