#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/53/7235344.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_7235344
loop_
_publ_author_name
'Mudududdla, Ramesh'
'Sharma, Rohit'
'Guru, Santosh K.'
'Kushwaha, Manoj'
'Gupta, Ajai P.'
'Bharate, Sonali S.'
'Aravinda, Subrayashastry'
'Kant, Rajni'
'Bhushan, Shashi'
'Vishwakarma, Ram A.'
'Bharate, Sandip B.'
_publ_section_title
;
 Trifluoroacetic acid catalyzed thiophenylmethylation and
 thioalkylmethylation of lactams and phenols via domino three-component
 reaction in water
;
_journal_issue                   27
_journal_name_full               'RSC Adv.'
_journal_page_first              14081
_journal_paper_doi               10.1039/C3RA47874B
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C16 H12 F1 N1 O3 S1'
_chemical_formula_sum            'C16 H12 F N O3 S'
_chemical_formula_weight         317.33
_chemical_name_systematic
; 
 5-fluoro-1-(((4-methoxyphenyl)thio)methyl)indoline-2,3-dione 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                90.000(5)
_cell_angle_beta                 107.615(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   21.243(5)
_cell_length_b                   5.558(5)
_cell_length_c                   13.288(5)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      4.2
_cell_volume                     1495.3(15)
_computing_cell_refinement       'Crysalis PRO (Oxford Diffraction,2010)'
_computing_data_collection       'Crysalis PRO (Oxford Diffraction,2010)'
_computing_data_reduction        'Crysalis PRO (Oxford Diffraction,2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, sapphire3'
_diffrn_measurement_method       'omega scan'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.1153
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5636
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction,2010)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0518
_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)+(0.0029P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                1337
_reflns_number_total             2926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra47874b1.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235344
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_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
C1 C 0.2619(2) 0.2466(8) 0.1389(3) 0.0643(12) Uani 1 1 d
C2 C 0.31129(16) 0.2880(6) 0.3321(3) 0.0543(10) Uani 1 1 d
C3 C 0.36460(17) 0.1511(6) 0.4190(3) 0.0555(10) Uani 1 1 d
C4 C 0.38732(16) -0.0378(5) 0.3623(3) 0.0473(9) Uani 1 1 d
C5 C 0.4339(2) -0.2185(7) 0.3979(4) 0.0596(11) Uani 1 1 d
C6 C 0.44337(17) -0.3684(6) 0.3241(4) 0.0593(11) Uani 1 1 d
C7 C 0.4107(2) -0.3513(7) 0.2176(4) 0.0620(11) Uani 1 1 d
C8 C 0.36408(19) -0.1699(7) 0.1817(3) 0.0550(10) Uani 1 1 d
C9 C 0.35324(15) -0.0149(6) 0.2552(3) 0.0451(9) Uani 1 1 d
C10 C 0.15643(14) 0.0565(6) 0.1922(3) 0.0474(9) Uani 1 1 d
C11 C 0.16689(18) -0.1153(6) 0.2709(3) 0.0595(11) Uani 1 1 d
C12 C 0.13428(19) -0.1009(6) 0.3461(3) 0.0594(11) Uani 1 1 d
C13 C 0.09009(16) 0.0843(5) 0.3427(3) 0.0463(9) Uani 1 1 d
C14 C 0.08077(17) 0.2594(6) 0.2662(3) 0.0505(10) Uani 1 1 d
C15 C 0.11276(17) 0.2440(6) 0.1894(3) 0.0507(10) Uani 1 1 d
C16 C 0.0149(2) 0.2708(8) 0.4196(4) 0.0653(12) Uani 1 1 d
N1 N 0.30893(13) 0.1824(5) 0.2384(2) 0.0514(8) Uani 1 1 d
O1 O 0.27963(11) 0.4588(4) 0.3471(2) 0.0774(9) Uani 1 1 d
O2 O 0.38104(13) 0.2023(4) 0.5113(2) 0.0821(9) Uani 1 1 d
O3 O 0.05800(11) 0.0769(4) 0.41805(18) 0.0588(7) Uani 1 1 d
S1 S 0.19586(5) 0.02870(18) 0.09254(8) 0.0699(4) Uani 1 1 d
F1 F 0.48713(10) -0.5531(3) 0.35573(19) 0.0966(9) Uani 1 1 d
H1B H 0.2832(14) 0.253(5) 0.086(2) 0.060(11) Uiso 1 1 d
H11 H 0.1994(13) -0.242(4) 0.276(2) 0.054(9) Uiso 1 1 d
H1A H 0.2438(16) 0.430(5) 0.147(3) 0.101(13) Uiso 1 1 d
H16C H 0.0395(15) 0.441(5) 0.434(3) 0.090(13) Uiso 1 1 d
H12 H 0.1401(15) -0.222(5) 0.398(3) 0.090(14) Uiso 1 1 d
H14 H 0.0495(14) 0.394(5) 0.264(2) 0.074(11) Uiso 1 1 d
H7 H 0.4244(16) -0.465(5) 0.168(3) 0.096(13) Uiso 1 1 d
H15 H 0.1086(14) 0.375(4) 0.141(2) 0.072(11) Uiso 1 1 d
H16B H -0.0055(15) 0.230(5) 0.477(2) 0.069(11) Uiso 1 1 d
H16A H -0.0174(16) 0.277(6) 0.361(3) 0.073(14) Uiso 1 1 d
H5 H 0.4521(15) -0.227(5) 0.465(2) 0.061(12) Uiso 1 1 d
H8 H 0.3448(14) -0.152(5) 0.112(2) 0.067(12) Uiso 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
N1 C1 S1 113.4(3)
N1 C1 H1B 109.7(19)
S1 C1 H1B 105.7(19)
N1 C1 H1A 107.8(18)
S1 C1 H1A 113.1(17)
H1B C1 H1A 107(2)
O1 C2 N1 128.1(4)
O1 C2 C3 125.3(4)
N1 C2 C3 106.6(3)
O2 C3 C4 131.2(4)
O2 C3 C2 124.3(4)
C4 C3 C2 104.5(3)
C5 C4 C9 120.7(3)
C5 C4 C3 131.1(4)
C9 C4 C3 108.1(3)
C6 C5 C4 116.6(4)
C6 C5 H5 127(2)
C4 C5 H5 117(2)
C5 C6 F1 118.7(4)
C5 C6 C7 124.4(4)
F1 C6 C7 116.9(3)
C8 C7 C6 119.1(4)
C8 C7 H7 123(2)
C6 C7 H7 118(2)
C9 C8 C7 117.8(4)
C9 C8 H8 123(2)
C7 C8 H8 119(2)
C8 C9 C4 121.4(3)
C8 C9 N1 128.3(4)
C4 C9 N1 110.3(3)
C11 C10 C15 119.4(3)
C11 C10 S1 120.0(3)
C15 C10 S1 120.5(3)
C12 C11 C10 120.4(3)
C12 C11 H11 119.7(16)
C10 C11 H11 119.8(16)
C13 C12 C11 120.2(4)
C13 C12 H12 120(2)
C11 C12 H12 120(2)
O3 C13 C12 115.8(3)
O3 C13 C14 124.5(3)
C12 C13 C14 119.7(3)
C13 C14 C15 120.3(3)
C13 C14 H14 119.8(17)
C15 C14 H14 119.8(17)
C10 C15 C14 119.9(3)
C10 C15 H15 121.0(17)
C14 C15 H15 118.6(17)
O3 C16 H16C 113.0(17)
O3 C16 H16B 105.5(17)
H16C C16 H16B 111(2)
O3 C16 H16A 111(2)
H16C C16 H16A 109(3)
H16B C16 H16A 106(3)
C2 N1 C9 110.5(3)
C2 N1 C1 123.7(3)
C9 N1 C1 125.4(3)
C13 O3 C16 117.0(3)
C10 S1 C1 100.34(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.440(4)
C1 S1 1.814(4)
C1 H1B 0.94(3)
C1 H1A 1.11(3)
C2 O1 1.214(3)
C2 N1 1.364(4)
C2 C3 1.550(5)
C3 O2 1.204(4)
C3 C4 1.457(4)
C4 C5 1.388(4)
C4 C9 1.393(4)
C5 C6 1.348(5)
C5 H5 0.86(3)
C6 F1 1.363(4)
C6 C7 1.379(5)
C7 C8 1.392(5)
C7 H7 1.02(3)
C8 C9 1.373(4)
C8 H8 0.90(3)
C9 N1 1.418(4)
C10 C11 1.384(4)
C10 C15 1.388(4)
C10 S1 1.775(3)
C11 C12 1.379(5)
C11 H11 0.97(2)
C12 C13 1.385(4)
C12 H12 0.94(3)
C13 O3 1.372(3)
C13 C14 1.377(4)
C14 C15 1.390(4)
C14 H14 1.00(3)
C15 H15 0.96(3)
C16 O3 1.419(4)
C16 H16C 1.07(3)
C16 H16B 1.01(3)
C16 H16A 0.87(3)
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
O1 C2 C3 O2 -1.1(6)
N1 C2 C3 O2 177.6(3)
O1 C2 C3 C4 179.3(3)
N1 C2 C3 C4 -2.0(3)
O2 C3 C4 C5 1.4(7)
C2 C3 C4 C5 -179.0(4)
O2 C3 C4 C9 -178.5(4)
C2 C3 C4 C9 1.1(4)
C9 C4 C5 C6 -0.6(5)
C3 C4 C5 C6 179.5(3)
C4 C5 C6 F1 -178.0(3)
C4 C5 C6 C7 0.7(6)
C5 C6 C7 C8 -0.6(6)
F1 C6 C7 C8 178.2(3)
C6 C7 C8 C9 0.4(5)
C7 C8 C9 C4 -0.3(5)
C7 C8 C9 N1 179.8(3)
C5 C4 C9 C8 0.4(5)
C3 C4 C9 C8 -179.7(3)
C5 C4 C9 N1 -179.7(3)
C3 C4 C9 N1 0.2(4)
C15 C10 C11 C12 0.0(6)
S1 C10 C11 C12 -177.2(3)
C10 C11 C12 C13 0.8(6)
C11 C12 C13 O3 177.2(3)
C11 C12 C13 C14 -2.5(6)
O3 C13 C14 C15 -176.3(3)
C12 C13 C14 C15 3.5(5)
C11 C10 C15 C14 0.9(5)
S1 C10 C15 C14 178.1(3)
C13 C14 C15 C10 -2.7(6)
O1 C2 N1 C9 -179.2(3)
C3 C2 N1 C9 2.2(3)
O1 C2 N1 C1 -6.2(6)
C3 C2 N1 C1 175.2(3)
C8 C9 N1 C2 178.3(3)
C4 C9 N1 C2 -1.6(4)
C8 C9 N1 C1 5.4(5)
C4 C9 N1 C1 -174.5(3)
S1 C1 N1 C2 -104.3(4)
S1 C1 N1 C9 67.7(4)
C12 C13 O3 C16 177.0(3)
C14 C13 O3 C16 -3.3(5)
C11 C10 S1 C1 -102.4(3)
C15 C10 S1 C1 80.4(3)
N1 C1 S1 C10 65.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339256
