#------------------------------------------------------------------------------
#$Date: 2021-09-03 23:23:46 +0300 (Fri, 03 Sep 2021) $
#$Revision: 268429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519004.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_4519004
loop_
_publ_author_name
'Bhattacharya, Anwesha'
'Thirupathi, Annaram'
'Natarajan, Pradeep'
'Peruncheralathan, Saravanan'
_publ_section_title
;
 Chemoselective Ullmann Reaction of α-Trisubstituted Thioamides:
 Synthesis of Novel 2-Iminobenzothiolanes.
;
_journal_issue                   32
_journal_name_full               'ACS omega'
_journal_page_first              21169
_journal_page_last               21180
_journal_paper_doi               10.1021/acsomega.1c03410
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C16 H12 N2 S'
_chemical_formula_sum            'C16 H12 N2 S'
_chemical_formula_weight         264.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                106.308(2)
_cell_angle_beta                 104.374(2)
_cell_angle_gamma                103.637(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1526(2)
_cell_length_b                   9.0963(2)
_cell_length_c                   10.4069(2)
_cell_measurement_reflns_used    9073
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9820
_cell_measurement_theta_min      4.7100
_cell_volume                     677.68(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9750
_diffrn_measured_fraction_theta_max 0.9750
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -105.00 -36.00   0.15    0.20    --  -38.50 -35.00 143.00  460
  2  ω    -42.00  27.90   0.15    0.20    --  -38.50  35.00 -59.00  466
  3  ω    -18.00  51.90   0.15    0.20    --   49.31 -35.00 143.00  466
  4  ω     46.00 115.00   0.15    0.20    --   49.31  35.00 -59.00  460
  5  ω    103.00 172.00   0.15    0.80    --  106.38  35.00 -59.00  460
  6  ω     40.00 109.00   0.15    0.80    --  106.38 -35.00 143.00  460
  7  ω    -42.00  27.00   0.15    0.20    --  -38.50  37.00-180.00  460
  8  ω   -108.00 -33.00   0.15    0.20    --  -38.50 -19.00   0.00  500
  9  ω     24.00  99.00   0.15    0.20    --   49.31-125.00   0.00  500
 10  ω     46.00 115.00   0.15    0.20    --   49.31  37.00-180.00  460
 11  ω      2.00  83.90   0.15    0.20    --   49.31 -99.00  60.00  546
 12  ω    102.00 171.00   0.15    0.80    --  106.38  45.00 -30.00  460
 13  ω     38.00 113.90   0.15    0.80    --  106.38 -15.00 -30.00  506
 14  ω     38.00 110.00   0.15    0.80    --  106.38 -30.00 -60.00  480
 15  ω     98.00 173.90   0.15    0.80    --  106.38  15.00 -90.00  506
 16  ω     44.00 119.00   0.15    0.80    --  106.38 -61.00  60.00  500
 17  ω    102.00 171.00   0.15    0.80    --  106.38  45.00 -90.00  460
 18  ω     42.00 117.00   0.15    0.80    --  106.38-125.00-120.00  500
 19  ω     42.00 117.00   0.15    0.80    --  106.38-125.00 120.00  500
 20  ω     44.00 119.00   0.15    0.80    --  106.38 -61.00-120.00  500
 21  ω     42.00 111.00   0.15    0.80    --  106.38 -45.00  60.00  460
 22  ω     44.00 119.00   0.15    0.80    --  106.38 -61.00 -90.00  500
 23  ω    103.00 175.00   0.15    0.80    --  106.38  30.00   0.00  480
 24  ω     44.00 119.00   0.15    0.80    --  106.38 -61.00-180.00  500
 25  ω     42.00 117.00   0.15    0.80    --  106.38-125.00 -60.00  500
 26  ω     42.00 117.00   0.15    0.80    --  106.38-125.00-180.00  500
 27  ω     38.00 110.00   0.15    0.80    --  106.38 -94.00   0.00  480
 28  ω     38.00 110.00   0.15    0.80    --  106.38 -94.00-180.00  480
 29  ω     26.00 113.00   0.15    0.20    --   49.31  77.00-150.00  580
 30  ω     26.00 113.00   0.15    0.20    --   49.31  77.00   0.00  580
 31  ω     26.00 113.00   0.15    0.20    --   49.31  77.00 -60.00  580
 32  ω     38.00 110.90   0.15    0.20    --   49.31  57.00  90.00  486
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0841162000
_diffrn_orient_matrix_UB_12      0.1859345000
_diffrn_orient_matrix_UB_13      0.0547707000
_diffrn_orient_matrix_UB_21      -0.1600161000
_diffrn_orient_matrix_UB_22      0.0183068000
_diffrn_orient_matrix_UB_23      0.0489204000
_diffrn_orient_matrix_UB_31      0.0998904000
_diffrn_orient_matrix_UB_32      -0.0003164000
_diffrn_orient_matrix_UB_33      0.1464473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10388
_diffrn_reflns_theta_full        77.3902
_diffrn_reflns_theta_max         77.39
_diffrn_reflns_theta_min         4.70
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2954
_exptl_crystal_description       needle
_exptl_crystal_F_000             277.3708
_exptl_crystal_preparation       'Slow diffusion'
_exptl_crystal_recrystallization_method 'Slow evapouration'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.1951
_refine_diff_density_min         -0.2711
_refine_diff_density_rms         0.0445
_refine_ls_d_res_high            0.7900
_refine_ls_d_res_low             9.4034
_refine_ls_goodness_of_fit_ref   1.0462
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0462
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0539P)²+0.2015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2645
_reflns_number_total             2813
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao1c03410_si_002.cif
_cod_data_source_block           PERU_AW_73
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_ambient_temperature' value '291 (2)' was changed
to '291(2)' -- the value was reformatted.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519004
_chemical_oxdiff_formula         'C32 H24 N4 S2 '
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C5(H5), C12(H12), C6(H6), C14(H14), C7(H7), C13(H13), C16(H16),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_olex2_submission_original_sample_id AW_74
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.036
_oxdiff_exptl_absorpt_empirical_full_min 0.382
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-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_refinement_flags_posn
S1 S 0.52144(5) 0.41504(5) 0.69463(4) 0.05098(15) Uani 1.000000 .
N10 N 0.17573(19) 0.31976(17) 0.51757(15) 0.0528(3) Uani 1.000000 .
C4 C 0.4355(2) 0.64571(19) 0.85679(16) 0.0430(3) Uani 1.000000 .
C3 C 0.2761(2) 0.57160(19) 0.72051(16) 0.0441(3) Uani 1.000000 .
C20 C 0.5704(2) 0.57722(19) 0.85447(16) 0.0443(3) Uani 1.000000 .
N18 N -0.0195(2) 0.4965(2) 0.7777(2) 0.0710(5) Uani 1.000000 .
C11 C 0.2012(2) 0.1826(2) 0.42884(17) 0.0479(4) Uani 1.000000 .
C24 C 0.7257(2) 0.6338(2) 0.97104(18) 0.0544(4) Uani 1.000000 .
H24 H 0.8158(2) 0.5875(2) 0.96955(18) 0.0653(5) Uiso 1.000000 R
C17 C 0.1082(2) 0.5268(2) 0.75094(18) 0.0497(4) Uani 1.000000 .
C21 C 0.3004(2) 0.41874(19) 0.62864(16) 0.0439(3) Uani 1.000000 .
C5 C 0.4555(3) 0.7732(2) 0.97570(18) 0.0529(4) Uani 1.000000 .
H5 H 0.3660(3) 0.8203(2) 0.97716(18) 0.0634(5) Uiso 1.000000 R
C19 C 0.2696(3) 0.6882(2) 0.6379(2) 0.0569(4) Uani 1.000000 .
H19a H 0.252(2) 0.7836(8) 0.6932(7) 0.0854(6) Uiso 1.000000 GR
H19b H 0.3802(8) 0.7184(14) 0.6198(14) 0.0854(6) Uiso 1.000000 GR
H19c H 0.1720(12) 0.6352(7) 0.5492(7) 0.0854(6) Uiso 1.000000 GR
C12 C 0.1888(3) 0.1704(2) 0.2914(2) 0.0572(4) Uani 1.000000 .
H12 H 0.1666(3) 0.2516(2) 0.2591(2) 0.0686(5) Uiso 1.000000 R
C6 C 0.6102(3) 0.8302(2) 1.09264(19) 0.0602(5) Uani 1.000000 .
H6 H 0.6244(3) 0.9153(2) 1.17351(19) 0.0723(5) Uiso 1.000000 R
C14 C 0.2387(3) -0.0861(2) 0.2474(2) 0.0638(5) Uani 1.000000 .
H14 H 0.2536(3) -0.1752(2) 0.1871(2) 0.0766(6) Uiso 1.000000 R
C7 C 0.7436(3) 0.7609(2) 1.08964(19) 0.0602(5) Uani 1.000000 .
H7 H 0.8471(3) 0.8005(2) 1.16874(19) 0.0722(5) Uiso 1.000000 R
C13 C 0.2097(3) 0.0365(2) 0.2015(2) 0.0672(5) Uani 1.000000 .
H13 H 0.2041(3) 0.0295(2) 0.1095(2) 0.0807(6) Uiso 1.000000 R
C16 C 0.2263(3) 0.0578(2) 0.4729(2) 0.0690(5) Uani 1.000000 .
H16 H 0.2307(3) 0.0634(2) 0.5643(2) 0.0828(7) Uiso 1.000000 R
C15 C 0.2453(3) -0.0758(3) 0.3819(2) 0.0716(6) Uani 1.000000 .
H15 H 0.2627(3) -0.1593(3) 0.4128(2) 0.0859(7) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C21 S1 C20 91.97(7) . . ?
C21 N10 C11 120.72(14) . . ?
C20 C4 C3 114.30(13) . . ?
C5 C4 C3 125.53(14) . . ?
C5 C4 C20 120.15(15) . . ?
C17 C3 C4 110.50(13) . . ?
C21 C3 C4 106.71(12) . . ?
C21 C3 C17 109.71(13) . . ?
C19 C3 C4 111.45(13) . . ?
C19 C3 C17 109.93(13) . . ?
C19 C3 C21 108.47(13) . . ?
C4 C20 S1 113.96(12) . . ?
C24 C20 S1 125.15(13) . . ?
C24 C20 C4 120.88(15) . . ?
C12 C11 N10 118.45(15) . . ?
C16 C11 N10 122.14(16) . . ?
C16 C11 C12 119.29(16) . . ?
H24 C24 C20 120.82(10) . . ?
C7 C24 C20 118.37(17) . . ?
C7 C24 H24 120.82(11) . . ?
N18 C17 C3 177.99(19) . . ?
N10 C21 S1 127.81(12) . . ?
C3 C21 S1 111.32(11) . . ?
C3 C21 N10 120.74(14) . . ?
H5 C5 C4 120.38(10) . . ?
C6 C5 C4 119.25(16) . . ?
C6 C5 H5 120.38(11) . . ?
H19a C19 C3 109.5 . . ?
H19b C19 C3 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C3 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H12 C12 C11 120.11(10) . . ?
C13 C12 C11 119.78(17) . . ?
C13 C12 H12 120.11(12) . . ?
H6 C6 C5 119.89(11) . . ?
C7 C6 C5 120.23(17) . . ?
C7 C6 H6 119.89(11) . . ?
C13 C14 H14 120.24(11) . . ?
C15 C14 H14 120.24(12) . . ?
C15 C14 C13 119.52(17) . . ?
C6 C7 C24 121.12(17) . . ?
H7 C7 C24 119.44(11) . . ?
H7 C7 C6 119.44(11) . . ?
C14 C13 C12 120.48(18) . . ?
H13 C13 C12 119.76(12) . . ?
H13 C13 C14 119.76(11) . . ?
H16 C16 C11 119.80(11) . . ?
C15 C16 C11 120.41(18) . . ?
C15 C16 H16 119.80(12) . . ?
C16 C15 C14 120.47(19) . . ?
H15 C15 C14 119.77(12) . . ?
H15 C15 C16 119.77(12) . . ?
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 C20 1.7655(16) . ?
S1 C21 1.7743(16) . ?
N10 C11 1.422(2) . ?
N10 C21 1.257(2) . ?
C4 C3 1.513(2) . ?
C4 C20 1.388(2) . ?
C4 C5 1.381(2) . ?
C3 C17 1.471(2) . ?
C3 C21 1.537(2) . ?
C3 C19 1.544(2) . ?
C20 C24 1.385(2) . ?
N18 C17 1.135(2) . ?
C11 C12 1.380(2) . ?
C11 C16 1.377(3) . ?
C24 H24 0.9300 . ?
C24 C7 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C19 H19a 0.9600 . ?
C19 H19b 0.9600 . ?
C19 H19c 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(3) . ?
C14 C15 1.363(3) . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.383(3) . ?
C15 H15 0.9300 . ?
