#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:26:50 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255998 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126828.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_7126828
loop_
_publ_author_name
'Sundaravelu, Nallappan'
'Sekar, Govindasamy'
_publ_section_title
;
 Cu-Catalyzed one-pot synthesis of thiochromeno-quinolinone and
 thiochromeno-thioflavone via oxidative double hetero Michael addition
 using in situ generated nucleophiles.
;
_journal_issue                   62
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8826
_journal_page_last               8829
_journal_paper_doi               10.1039/d0cc03210g
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H13 F O S2'
_chemical_formula_sum            'C22 H13 F O S2'
_chemical_formula_weight         376.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-17 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.113(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3658(11)
_cell_length_b                   12.2954(9)
_cell_length_c                   12.4661(14)
_cell_measurement_reflns_used    1416
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      2.47
_cell_volume                     1703.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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  0.0594
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10253
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.353
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       Block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0425
_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)+(0.0359P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1766
_reflns_number_total             3000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03210g2.cif
_cod_data_source_block           735
_cod_depositor_comments
'Adding full bibliography for 7126828--7126829.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126828
_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   0.952
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.1641(3) -0.0089(2) -0.0644(2) 0.0370(7) Uani 1 1 d . . . . .
C2 C 0.1577(3) -0.1066(2) -0.1236(3) 0.0493(9) Uani 1 1 d . . . . .
H2 H 0.2199 -0.1570 -0.1072 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0604(4) -0.1275(3) -0.2049(3) 0.0587(10) Uani 1 1 d . . . . .
H3 H 0.0569 -0.1920 -0.2443 0.070 Uiso 1 1 calc R U . . .
C4 C -0.0343(3) -0.0537(3) -0.2299(3) 0.0595(10) Uani 1 1 d . . . . .
H4 H -0.1011 -0.0691 -0.2850 0.071 Uiso 1 1 calc R U . . .
C5 C -0.0282(3) 0.0424(2) -0.1725(3) 0.0481(9) Uani 1 1 d . . . . .
H5 H -0.0910 0.0921 -0.1896 0.058 Uiso 1 1 calc R U . . .
C6 C 0.0710(3) 0.0666(2) -0.0888(2) 0.0368(7) Uani 1 1 d . . . . .
C7 C 0.0735(3) 0.1715(2) -0.0308(2) 0.0371(7) Uani 1 1 d . . . . .
C8 C 0.1791(3) 0.20140(19) 0.0538(2) 0.0331(7) Uani 1 1 d . . . . .
C9 C 0.1715(3) 0.31449(19) 0.1008(2) 0.0372(7) Uani 1 1 d . . . . .
H9 H 0.0854 0.3283 0.0951 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3746(3) 0.2545(2) 0.2451(3) 0.0410(8) Uani 1 1 d . . . . .
C11 C 0.4731(3) 0.2823(2) 0.3266(3) 0.0550(9) Uani 1 1 d . . . . .
H11 H 0.4663 0.3382 0.3752 0.066 Uiso 1 1 calc R U . . .
C12 C 0.5803(3) 0.2283(3) 0.3363(3) 0.0631(10) Uani 1 1 d . . . . .
H12 H 0.6454 0.2469 0.3918 0.076 Uiso 1 1 calc R U . . .
C13 C 0.5913(3) 0.1464(3) 0.2639(3) 0.0599(10) Uani 1 1 d . . . . .
H13 H 0.6638 0.1093 0.2709 0.072 Uiso 1 1 calc R U . . .
C14 C 0.4954(3) 0.1193(2) 0.1810(3) 0.0485(9) Uani 1 1 d . . . . .
H14 H 0.5048 0.0653 0.1312 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3838(3) 0.1716(2) 0.1703(2) 0.0378(7) Uani 1 1 d . . . . .
C16 C 0.2780(3) 0.1384(2) 0.0861(2) 0.0349(7) Uani 1 1 d . . . . .
C17 C 0.2151(2) 0.40467(19) 0.0368(2) 0.0334(7) Uani 1 1 d . . . . .
C18 C 0.3091(3) 0.3911(2) -0.0174(2) 0.0402(8) Uani 1 1 d . . . . .
H18 H 0.3464 0.3236 -0.0156 0.048 Uiso 1 1 calc R U . . .
C19 C 0.3481(3) 0.4756(2) -0.0736(3) 0.0475(8) Uani 1 1 d . . . . .
H19 H 0.4117 0.4665 -0.1092 0.057 Uiso 1 1 calc R U . . .
C20 C 0.2906(3) 0.5728(2) -0.0754(3) 0.0517(9) Uani 1 1 d . . . . .
C21 C 0.1983(3) 0.5909(2) -0.0232(3) 0.0497(9) Uani 1 1 d . . . . .
H21 H 0.1616 0.6587 -0.0260 0.060 Uiso 1 1 calc R U . . .
C22 C 0.1610(3) 0.5065(2) 0.0335(2) 0.0399(8) Uani 1 1 d . . . . .
H22 H 0.0987 0.5174 0.0702 0.048 Uiso 1 1 calc R U . . .
F1 F 0.32806(19) 0.65661(14) -0.13153(19) 0.0889(7) Uani 1 1 d . . . . .
O1 O -0.01166(19) 0.23510(16) -0.05563(18) 0.0548(6) Uani 1 1 d . . . . .
S1 S 0.29254(7) 0.00867(5) 0.03624(7) 0.0475(3) Uani 1 1 d . . . . .
S2 S 0.23787(8) 0.31940(6) 0.24575(7) 0.0512(3) Uani 1 1 d . . . . .
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'
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'
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
C6 C1 C2 120.2(3) . . ?
C6 C1 S1 124.3(2) . . ?
C2 C1 S1 115.5(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 122.7(3) . . ?
C5 C6 C7 118.8(3) . . ?
O1 C7 C8 120.1(2) . . ?
O1 C7 C6 119.8(3) . . ?
C8 C7 C6 120.0(3) . . ?
C16 C8 C7 124.9(2) . . ?
C16 C8 C9 121.3(3) . . ?
C7 C8 C9 113.7(2) . . ?
C17 C9 C8 114.6(2) . . ?
C17 C9 S2 112.91(19) . . ?
C8 C9 S2 111.75(19) . . ?
C17 C9 H9 105.5 . . ?
C8 C9 H9 105.5 . . ?
S2 C9 H9 105.5 . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 S2 117.8(3) . . ?
C15 C10 S2 121.7(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 117.5(3) . . ?
C10 C15 C16 120.7(3) . . ?
C14 C15 C16 121.7(3) . . ?
C8 C16 C15 123.6(2) . . ?
C8 C16 S1 123.7(2) . . ?
C15 C16 S1 112.6(2) . . ?
C18 C17 C22 118.4(2) . . ?
C18 C17 C9 122.7(2) . . ?
C22 C17 C9 118.9(2) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 117.8(3) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 F1 118.1(3) . . ?
C19 C20 C21 123.4(3) . . ?
F1 C20 C21 118.4(3) . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C1 S1 C16 104.26(14) . . ?
C10 S2 C9 99.52(14) . . ?
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
C1 C6 1.392(4) . ?
C1 C2 1.404(4) . ?
C1 S1 1.728(3) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(4) . ?
C7 O1 1.233(3) . ?
C7 C8 1.468(4) . ?
C8 C16 1.355(4) . ?
C8 C9 1.518(3) . ?
C9 C17 1.509(3) . ?
C9 S2 1.807(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.387(4) . ?
C10 C15 1.401(4) . ?
C10 S2 1.748(3) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.477(4) . ?
C16 S1 1.732(3) . ?
C17 C18 1.388(4) . ?
C17 C22 1.391(3) . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(4) . ?
C19 H19 0.9300 . ?
C20 F1 1.363(3) . ?
C20 C21 1.363(4) . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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
C6 C1 C2 C3 0.1(4) . . . . ?
S1 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
S1 C1 C6 C5 179.9(2) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
S1 C1 C6 C7 0.7(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C1 C6 C7 O1 -179.8(3) . . . . ?
C5 C6 C7 O1 1.0(4) . . . . ?
C1 C6 C7 C8 2.2(4) . . . . ?
C5 C6 C7 C8 -177.0(2) . . . . ?
O1 C7 C8 C16 -179.0(3) . . . . ?
C6 C7 C8 C16 -1.0(4) . . . . ?
O1 C7 C8 C9 -1.6(4) . . . . ?
C6 C7 C8 C9 176.4(2) . . . . ?
C16 C8 C9 C17 91.2(3) . . . . ?
C7 C8 C9 C17 -86.3(3) . . . . ?
C16 C8 C9 S2 -38.9(3) . . . . ?
C7 C8 C9 S2 143.6(2) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
S2 C10 C11 C12 174.6(2) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C11 C10 C15 C14 -0.4(4) . . . . ?
S2 C10 C15 C14 -175.7(2) . . . . ?
C11 C10 C15 C16 177.4(3) . . . . ?
S2 C10 C15 C16 2.1(4) . . . . ?
C13 C14 C15 C10 1.8(4) . . . . ?
C13 C14 C15 C16 -176.0(3) . . . . ?
C7 C8 C16 C15 178.9(2) . . . . ?
C9 C8 C16 C15 1.7(4) . . . . ?
C7 C8 C16 S1 -2.9(4) . . . . ?
C9 C8 C16 S1 179.83(19) . . . . ?
C10 C15 C16 C8 19.7(4) . . . . ?
C14 C15 C16 C8 -162.7(3) . . . . ?
C10 C15 C16 S1 -158.6(2) . . . . ?
C14 C15 C16 S1 19.0(3) . . . . ?
C8 C9 C17 C18 -33.8(4) . . . . ?
S2 C9 C17 C18 95.7(3) . . . . ?
C8 C9 C17 C22 147.6(3) . . . . ?
S2 C9 C17 C22 -82.9(3) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C9 C17 C18 C19 -178.9(3) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 F1 -179.5(3) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
F1 C20 C21 C22 -179.8(3) . . . . ?
C20 C21 C22 C17 -0.6(4) . . . . ?
C18 C17 C22 C21 1.0(4) . . . . ?
C9 C17 C22 C21 179.6(3) . . . . ?
C6 C1 S1 C16 -3.7(3) . . . . ?
C2 C1 S1 C16 175.9(2) . . . . ?
C8 C16 S1 C1 4.8(3) . . . . ?
C15 C16 S1 C1 -176.88(19) . . . . ?
C11 C10 S2 C9 151.5(2) . . . . ?
C15 C10 S2 C9 -33.0(2) . . . . ?
C17 C9 S2 C10 -82.2(2) . . . . ?
C8 C9 S2 C10 48.8(2) . . . . ?
