#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/68/2216867.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216867
loop_
_publ_author_name
'Ming Li'
'Guo-Rui Cao'
'Li-Rong Weng'
_publ_section_title
;Diethyl
 5,5'-thiobis[2-amino-4-(4-fluorophenyl)-1-phenyl-1H-pyrrole-3-carboxylate]
;
_journal_coeditor_code           AT2503
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o21
_journal_page_last               o21
_journal_paper_doi               10.1107/S1600536807061545
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C38 H32 F2 N4 O4 S'
_chemical_formula_moiety         'C38 H32 F2 N4 O4 S'
_chemical_formula_sum            'C38 H32 F2 N4 O4 S'
_chemical_formula_weight         678.74
_chemical_name_systematic
;
Diethyl 5,5'-thiobis[2-amino-4-(4-fluorophenyl)-1-phenyl-1H-pyrrole-3-
carboxylate]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 106.944(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.158(3)
_cell_length_b                   19.160(4)
_cell_length_c                   14.958(3)
_cell_measurement_reflns_used    1735
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.33
_cell_measurement_theta_min      2.56
_cell_volume                     3333.2(13)
_computing_cell_refinement       'SAINT  (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL  (Bruker, 1999)'
_computing_publication_material  'SHELXTL (Bruker, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(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       'phi and omega scans'
_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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8487
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1645
_reflns_number_total             2942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            at2503.cif
_cod_data_source_block           I
_cod_original_cell_volume        3333.0(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2216867
_cod_database_fobs_code          2216867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.0000 0.02157(5) 0.2500 0.0518(3) Uani d S 1 . .
F F1 0.41195(19) -0.13211(10) 0.15342(15) 0.1094(7) Uani d . 1 . .
O O1 0.0803(2) 0.21900(12) -0.06429(16) 0.0943(8) Uani d . 1 . .
O O2 0.1802(2) 0.11943(13) -0.04003(15) 0.0918(8) Uani d D 1 . .
N N1 -0.0635(2) 0.13810(11) 0.13685(14) 0.0495(6) Uani d . 1 . .
N N2 -0.0895(2) 0.23284(12) 0.02943(17) 0.0715(8) Uani d D 1 . .
H H2A -0.1284 0.2575 0.0614 0.086 Uiso d RD 1 . .
H H2B -0.0521 0.2595 -0.0014 0.086 Uiso d RD 1 . .
C C1 0.2891(3) 0.04044(15) 0.13523(18) 0.0581(8) Uani d . 1 . .
H H1 0.3128 0.0867 0.1378 0.070 Uiso calc R 1 . .
C C2 0.3696(3) -0.01205(18) 0.14655(19) 0.0669(9) Uani d . 1 . .
H H2 0.4470 -0.0017 0.1566 0.080 Uiso calc R 1 . .
C C3 0.3327(3) -0.08003(18) 0.1426(2) 0.0680(9) Uani d . 1 . .
C C4 0.2211(3) -0.09736(16) 0.1275(2) 0.0687(9) Uani d . 1 . .
H H4 0.1986 -0.1439 0.1249 0.082 Uiso calc R 1 . .
C C5 0.1410(3) -0.04417(14) 0.11607(17) 0.0555(8) Uani d . 1 . .
H H5 0.0638 -0.0554 0.1055 0.067 Uiso calc R 1 . .
C C6 0.1734(2) 0.02548(14) 0.12005(16) 0.0458(7) Uani d . 1 . .
C C7 0.0855(2) 0.07966(13) 0.11175(17) 0.0460(7) Uani d . 1 A .
C C8 0.0077(2) 0.07882(13) 0.16089(17) 0.0455(7) Uani d . 1 . .
C C9 -0.0292(3) 0.17553(14) 0.07162(18) 0.0532(8) Uani d . 1 A .
C C10 0.0626(3) 0.14193(14) 0.05373(18) 0.0518(7) Uani d . 1 . .
C C11 0.1072(3) 0.16536(19) -0.0206(2) 0.0672(9) Uani d . 1 A .
C C12 0.2371(9) 0.1505(5) -0.1060(7) 0.079(3) Uani d PDU 0.588(14) A 1
H H12A 0.2721 0.1950 -0.0832 0.094 Uiso calc PR 0.588(14) A 1
H H12B 0.1829 0.1570 -0.1674 0.094 Uiso calc PR 0.588(14) A 1
C C13 0.3270(9) 0.0970(6) -0.1087(6) 0.095(3) Uani d PDU 0.588(14) A 1
H H13A 0.3698 0.1129 -0.1496 0.142 Uiso calc PR 0.588(14) A 1
H H13B 0.2903 0.0535 -0.1312 0.142 Uiso calc PR 0.588(14) A 1
H H13C 0.3783 0.0907 -0.0469 0.142 Uiso calc PR 0.588(14) A 1
C C12' 0.2111(9) 0.1190(9) -0.1291(6) 0.080(4) Uani d PDU 0.412(14) A 2
H H12C 0.1642 0.1513 -0.1743 0.095 Uiso calc PR 0.412(14) A 2
H H12D 0.2047 0.0727 -0.1563 0.095 Uiso calc PR 0.412(14) A 2
C C13' 0.3355(12) 0.1429(10) -0.0939(9) 0.113(5) Uani d PDU 0.412(14) A 2
H H13D 0.3671 0.1462 -0.1456 0.170 Uiso calc PR 0.412(14) A 2
H H13E 0.3791 0.1099 -0.0493 0.170 Uiso calc PR 0.412(14) A 2
H H13F 0.3388 0.1878 -0.0648 0.170 Uiso calc PR 0.412(14) A 2
C C14 -0.1757(3) 0.14464(15) 0.14982(18) 0.0524(7) Uani d . 1 . .
C C15 -0.2597(3) 0.09787(17) 0.1047(2) 0.0688(9) Uani d . 1 . .
H H15 -0.2425 0.0621 0.0690 0.083 Uiso calc R 1 . .
C C16 -0.3690(3) 0.1044(2) 0.1128(2) 0.0853(11) Uani d . 1 . .
H H16 -0.4256 0.0726 0.0827 0.102 Uiso calc R 1 . .
C C17 -0.3948(4) 0.1564(3) 0.1640(3) 0.0874(12) Uani d . 1 . .
H H17 -0.4694 0.1605 0.1682 0.105 Uiso calc R 1 . .
C C18 -0.3129(4) 0.2029(2) 0.2097(3) 0.0886(12) Uani d . 1 . .
H H18 -0.3316 0.2384 0.2452 0.106 Uiso calc R 1 . .
C C19 -0.2004(3) 0.19735(16) 0.2033(2) 0.0741(10) Uani d . 1 . .
H H19 -0.1438 0.2287 0.2345 0.089 Uiso calc R 1 . .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C8 2 102.35(16) yes
C11 O2 C12 . 110.3(4) ?
C11 O2 C12' . 123.7(6) ?
C12 O2 C12' . 28.1(4) ?
C9 N1 C8 . 108.2(2) ?
C9 N1 C14 . 123.2(2) ?
C8 N1 C14 . 124.8(2) ?
C9 N2 H2A . 118.1 ?
C9 N2 H2B . 114.3 ?
H2A N2 H2B . 113.4 ?
C2 C1 C6 . 121.2(3) ?
C2 C1 H1 . 119.4 ?
C6 C1 H1 . 119.4 ?
C3 C2 C1 . 118.4(3) ?
C3 C2 H2 . 120.8 ?
C1 C2 H2 . 120.8 ?
C4 C3 F1 . 118.7(3) ?
C4 C3 C2 . 122.7(3) ?
F1 C3 C2 . 118.6(3) ?
C3 C4 C5 . 118.4(3) ?
C3 C4 H4 . 120.8 ?
C5 C4 H4 . 120.8 ?
C4 C5 C6 . 121.4(3) ?
C4 C5 H5 . 119.3 ?
C6 C5 H5 . 119.3 ?
C1 C6 C5 . 117.9(3) ?
C1 C6 C7 . 123.1(2) ?
C5 C6 C7 . 119.0(3) ?
C8 C7 C10 . 106.9(2) ?
C8 C7 C6 . 123.4(2) ?
C10 C7 C6 . 129.6(2) ?
C7 C8 N1 . 109.0(2) ?
C7 C8 S1 . 128.4(2) ?
N1 C8 S1 . 122.32(19) ?
N2 C9 N1 . 121.0(3) ?
N2 C9 C10 . 129.8(3) ?
N1 C9 C10 . 109.0(2) ?
C9 C10 C11 . 120.7(3) ?
C9 C10 C7 . 107.0(2) ?
C11 C10 C7 . 131.7(3) ?
O1 C11 O2 . 122.2(3) ?
O1 C11 C10 . 125.2(3) ?
O2 C11 C10 . 112.6(3) ?
O2 C12 C13 . 103.1(6) ?
O2 C12 H12A . 111.1 ?
C13 C12 H12A . 111.1 ?
O2 C12 H12B . 111.1 ?
C13 C12 H12B . 111.1 ?
H12A C12 H12B . 109.1 ?
C12 C13 H13A . 109.5 ?
C12 C13 H13B . 109.5 ?
H13A C13 H13B . 109.5 ?
C12 C13 H13C . 109.5 ?
H13A C13 H13C . 109.5 ?
H13B C13 H13C . 109.5 ?
O2 C12' C13' . 100.0(9) ?
O2 C12' H12C . 111.8 ?
C13' C12' H12C . 111.8 ?
O2 C12' H12D . 111.8 ?
C13' C12' H12D . 111.8 ?
H12C C12' H12D . 109.5 ?
C12' C13' H13D . 109.5 ?
C12' C13' H13E . 109.5 ?
H13D C13' H13E . 109.5 ?
C12' C13' H13F . 109.5 ?
H13D C13' H13F . 109.5 ?
H13E C13' H13F . 109.5 ?
C19 C14 C15 . 120.4(3) ?
C19 C14 N1 . 121.3(3) ?
C15 C14 N1 . 118.3(3) ?
C16 C15 C14 . 119.7(3) ?
C16 C15 H15 . 120.1 ?
C14 C15 H15 . 120.1 ?
C17 C16 C15 . 120.5(4) ?
C17 C16 H16 . 119.7 ?
C15 C16 H16 . 119.7 ?
C16 C17 C18 . 120.7(4) ?
C16 C17 H17 . 119.6 ?
C18 C17 H17 . 119.6 ?
C17 C18 C19 . 120.0(3) ?
C17 C18 H18 . 120.0 ?
C19 C18 H18 . 120.0 ?
C14 C19 C18 . 118.6(3) ?
C14 C19 H19 . 120.7 ?
C18 C19 H19 . 120.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.750(2) yes
S1 C8 2 1.750(2) ?
F1 C3 . 1.363(3) yes
O1 C11 . 1.211(3) ?
O2 C11 . 1.341(4) ?
O2 C12 . 1.484(6) ?
O2 C12' . 1.485(8) ?
N1 C9 . 1.370(3) yes
N1 C8 . 1.409(3) yes
N1 C14 . 1.438(3) yes
N2 C9 . 1.368(3) yes
N2 H2A . 0.8989 ?
N2 H2B . 0.8954 ?
C1 C2 . 1.379(4) ?
C1 C6 . 1.388(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.373(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.350(4) ?
C4 C5 . 1.385(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.469(4) ?
C7 C8 . 1.356(3) ?
C7 C10 . 1.454(3) ?
C9 C10 . 1.380(4) ?
C10 C11 . 1.443(4) ?
C12 C13 . 1.507(8) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C12' C13' . 1.520(9) ?
C12' H12C . 0.9700 ?
C12' H12D . 0.9700 ?
C13' H13D . 0.9600 ?
C13' H13E . 0.9600 ?
C13' H13F . 0.9600 ?
C14 C19 . 1.375(4) ?
C14 C15 . 1.378(4) ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.349(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.363(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.403(5) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A F1 3_455 0.90 2.49 3.181(3) 133.7 y
N2 H2B O1 . 0.90 2.23 2.825(3) 123.8 y
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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . -0.1(4)
C1 C2 C3 C4 . 0.4(5)
C1 C2 C3 F1 . 179.8(3)
F1 C3 C4 C5 . -179.6(2)
C2 C3 C4 C5 . -0.3(5)
C3 C4 C5 C6 . -0.2(4)
C2 C1 C6 C5 . -0.4(4)
C2 C1 C6 C7 . 177.2(2)
C4 C5 C6 C1 . 0.5(4)
C4 C5 C6 C7 . -177.2(2)
C1 C6 C7 C8 . -129.7(3)
C5 C6 C7 C8 . 47.9(3)
C1 C6 C7 C10 . 50.3(4)
C5 C6 C7 C10 . -132.1(3)
C10 C7 C8 N1 . -0.2(3)
C6 C7 C8 N1 . 179.8(2)
C10 C7 C8 S1 . -173.5(2)
C6 C7 C8 S1 . 6.5(4)
C9 N1 C8 C7 . 0.4(3)
C14 N1 C8 C7 . 159.1(2)
C9 N1 C8 S1 . 174.16(19)
C14 N1 C8 S1 . -27.2(3)
C8 S1 C8 C7 2 128.1(3)
C8 S1 C8 N1 2 -44.36(16)
C8 N1 C9 N2 . 174.3(2)
C14 N1 C9 N2 . 15.2(4)
C8 N1 C9 C10 . -0.4(3)
C14 N1 C9 C10 . -159.5(2)
N2 C9 C10 C11 . -1.6(5)
N1 C9 C10 C11 . 172.5(2)
N2 C9 C10 C7 . -173.8(3)
N1 C9 C10 C7 . 0.2(3)
C8 C7 C10 C9 . 0.0(3)
C6 C7 C10 C9 . 180.0(3)
C8 C7 C10 C11 . -171.0(3)
C6 C7 C10 C11 . 9.0(5)
C12 O2 C11 O1 . 11.3(7)
C12' O2 C11 O1 . -16.7(7)
C12 O2 C11 C10 . -171.2(6)
C12' O2 C11 C10 . 160.8(6)
C9 C10 C11 O1 . 9.6(5)
C7 C10 C11 O1 . 179.6(3)
C9 C10 C11 O2 . -167.8(3)
C7 C10 C11 O2 . 2.2(5)
C11 O2 C12 C13 . 171.9(9)
C12' O2 C12 C13 . -63.9(13)
C11 O2 C12' C13' . 110.4(13)
C12 O2 C12' C13' . 41.5(12)
C9 N1 C14 C19 . -82.7(3)
C8 N1 C14 C19 . 121.7(3)
C9 N1 C14 C15 . 95.3(3)
C8 N1 C14 C15 . -60.3(3)
C19 C14 C15 C16 . 0.5(4)
N1 C14 C15 C16 . -177.5(3)
C14 C15 C16 C17 . 0.4(5)
C15 C16 C17 C18 . -0.8(5)
C16 C17 C18 C19 . 0.4(5)
C15 C14 C19 C18 . -0.9(4)
N1 C14 C19 C18 . 177.0(3)
C17 C18 C19 C14 . 0.4(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 91603637
