#------------------------------------------------------------------------------
#$Date: 2021-09-03 23:23:23 +0300 (Fri, 03 Sep 2021) $
#$Revision: 268428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519003.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_4519003
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 H14 N2 O S'
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.37
_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     direct
_audit_creation_date             2021-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                96.180(2)
_cell_angle_beta                 92.803(2)
_cell_angle_gamma                108.433(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4476(2)
_cell_length_b                   9.4727(3)
_cell_length_c                   12.1525(3)
_cell_measurement_reflns_used    9680
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.2110
_cell_measurement_theta_min      3.6850
_cell_volume                     697.34(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.9816
_diffrn_measured_fraction_theta_max 0.9809
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -86.00  -6.00   0.50    0.38    --  -38.50 125.00 139.00  160
  2  ω   -102.00 -16.00   0.50    0.38    --  -38.50 146.00 -54.00  172
  3  ω     38.00 114.00   0.50    0.38    --   49.56-146.00-105.00  152
  4  ω     97.00 168.00   0.50    1.48    --  102.63 125.00 139.00  142
  5  ω     86.00 166.00   0.50    1.48    --  102.63 146.00 -54.00  160
  6  ω     38.00 112.00   0.50    1.48    --  102.63-125.00  61.00  148
  7  ω    -50.00  24.00   0.50    0.38    --  -38.50  57.00 -30.00  148
  8  ω    -42.00  28.00   0.50    0.38    --  -38.50  38.00 -90.00  140
  9  ω    -44.00  31.00   0.50    0.38    --  -38.50  19.00-120.00  150
 10  ω   -101.00 -27.00   0.50    0.38    --  -38.50 -57.00-120.00  148
 11  ω     28.00 101.00   0.50    0.38    --   49.56-125.00  61.00  146
 12  ω     38.00 107.00   0.50    1.48    --  102.63 -45.00   0.00  138
 13  ω     40.00 116.00   0.50    1.48    --  102.63 -61.00-150.00  152
 14  ω     98.00 167.00   0.50    1.48    --  102.63  45.00  60.00  138
 15  ω     35.00 106.00   0.50    1.48    --  102.63 -30.00 -90.00  142
 16  ω     90.00 165.00   0.50    1.48    --  102.63  61.00 -30.00  150
 17  ω     38.00 126.00   0.50    1.48    --  102.63 -77.00  30.00  176
 18  ω     98.00 167.00   0.50    1.48    --  102.63  45.00 -60.00  138
 19  ω     40.00 116.00   0.50    1.48    --  102.63 -61.00 -90.00  152
 20  ω     35.00 106.00   0.50    1.48    --  102.63 -30.00  30.00  142
 21  ω     90.00 165.00   0.50    1.48    --  102.63  61.00  30.00  150
 22  ω     97.00 168.00   0.50    1.48    --  102.63 125.00 -90.00  142
 23  ω     38.00 112.00   0.50    1.48    --  102.63-125.00 -30.00  148
 24  ω     90.00 165.00   0.50    1.48    --  102.63  61.00 -90.00  150
 25  ω     34.00 107.00   0.50    1.48    --  102.63 -94.00-150.00  146
 26  ω     38.00 112.00   0.50    1.48    --  102.63-125.00 150.00  148
 27  ω     35.00 106.00   0.50    1.48    --  102.63 -30.00 120.00  142
 28  ω     97.00 168.00   0.50    1.48    --  102.63 125.00 150.00  142
 29  ω     38.00 107.00   0.50    1.48    --  102.63 -45.00-180.00  138
 30  ω     39.00 128.00   0.50    1.48    --  102.63-146.00-105.00  178
 31  ω     38.00 107.00   0.50    0.38    --   49.56  57.00 150.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0232630000
_diffrn_orient_matrix_UB_12      0.1677653000
_diffrn_orient_matrix_UB_13      0.0219745000
_diffrn_orient_matrix_UB_21      -0.0372642000
_diffrn_orient_matrix_UB_22      0.0033208000
_diffrn_orient_matrix_UB_23      -0.1257520000
_diffrn_orient_matrix_UB_31      -0.2489905000
_diffrn_orient_matrix_UB_32      -0.0416560000
_diffrn_orient_matrix_UB_33      0.0094432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10340
_diffrn_reflns_theta_full        75.4136
_diffrn_reflns_theta_max         75.41
_diffrn_reflns_theta_min         3.67
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.3447
_exptl_crystal_description       needle
_exptl_crystal_F_000             297.4742
_exptl_crystal_preparation       'Slow diffusion method'
_exptl_crystal_recrystallization_method 'Sloww diffusion method'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4761
_refine_diff_density_min         -0.5019
_refine_diff_density_rms         0.1819
_refine_ls_d_res_high            0.7966
_refine_ls_d_res_low             12.0351
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0423
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0423
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0614P)²+0.3139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2787
_reflns_number_total             2827
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao1c03410_si_003.cif
_cod_data_source_block           PERU-AW-126
_cod_database_code               4519003
_chemical_oxdiff_formula         'C34 H26 N2 O2 S2 '
_diffrn_oxdiff_digest_frames
;
01c173412983e03366fedadbc873a52d230461692dc
;
_diffrn_oxdiff_digest_hkl
;
0148c6cbc59c88ad36608c219bd28697d4380f
;
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C16(H16), C14(H14), C4(H4), C6(H6), C15(H15), C5(H5),
 C13(H13)
2.b X=CH2 refined with riding coordinates:
 N18(H18a,H18b)
2.c Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c)
;
_olex2_submission_original_sample_id Peru_AW_126
_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 1.725
_oxdiff_exptl_absorpt_empirical_full_min 0.610
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
S9 S 0.53089(6) 0.66201(4) 0.13451(3) 0.02569(15) Uani 1.000000 .
O19 O 0.71700(19) 0.98598(12) 0.41539(9) 0.0306(3) Uani 1.000000 .
N10 N 0.3616(2) 0.53316(14) 0.31581(10) 0.0250(3) Uani 1.000000 .
N18 N 0.4857(2) 0.79628(15) 0.49050(11) 0.0304(3) Uani 1.000000 .
H18a H 0.4378(2) 0.85749(15) 0.53401(11) 0.0365(4) Uiso 1.000000 R
H18b H 0.4333(2) 0.69884(15) 0.49233(11) 0.0365(4) Uiso 1.000000 R
C3 C 0.8810(2) 0.80864(16) 0.27377(11) 0.0223(3) Uani 1.000000 .
C8 C 0.8066(2) 0.77734(16) 0.16153(12) 0.0232(3) Uani 1.000000 .
C2 C 0.7148(2) 0.73368(16) 0.35059(11) 0.0218(3) Uani 1.000000 .
C1 C 0.5143(2) 0.62892(15) 0.27563(11) 0.0221(3) Uani 1.000000 .
C17 C 0.6380(2) 0.85129(16) 0.42161(11) 0.0230(3) Uani 1.000000 .
C11 C 0.1661(2) 0.44200(16) 0.25175(12) 0.0240(3) Uani 1.000000 .
C12 C 0.0500(2) 0.49890(17) 0.17822(13) 0.0268(3) Uani 1.000000 .
H12 H 0.1074(2) 0.60050(17) 0.16506(13) 0.0321(4) Uiso 1.000000 R
C7 C 0.9434(3) 0.83239(18) 0.08016(12) 0.0279(3) Uani 1.000000 .
H7 H 0.8912(3) 0.80979(18) 0.00374(12) 0.0334(4) Uiso 1.000000 R
C16 C 0.0806(3) 0.29265(17) 0.27031(12) 0.0291(3) Uani 1.000000 .
H16 H 0.1590(3) 0.25310(17) 0.32024(12) 0.0350(4) Uiso 1.000000 R
C14 C -0.2349(3) 0.25931(19) 0.14397(14) 0.0324(4) Uani 1.000000 .
H14 H -0.3730(3) 0.19753(19) 0.10814(14) 0.0389(4) Uiso 1.000000 R
C4 C 1.0956(2) 0.89814(17) 0.30580(13) 0.0263(3) Uani 1.000000 .
H4 H 1.1477(2) 0.92086(17) 0.38222(13) 0.0315(4) Uiso 1.000000 R
C20 C 0.8074(3) 0.64335(18) 0.42642(12) 0.0278(3) Uani 1.000000 .
H20a H 0.8561(19) 0.5701(9) 0.38065(13) 0.0418(5) Uiso 1.000000 GR
H20b H 0.9321(13) 0.7119(2) 0.4753(7) 0.0418(5) Uiso 1.000000 GR
H20c H 0.6929(6) 0.5906(11) 0.4715(7) 0.0418(5) Uiso 1.000000 GR
C6 C 1.1583(3) 0.92126(18) 0.11357(13) 0.0301(3) Uani 1.000000 .
H6 H 1.2546(3) 0.95979(18) 0.05927(13) 0.0361(4) Uiso 1.000000 R
C15 C -0.1189(3) 0.20163(18) 0.21591(14) 0.0339(4) Uani 1.000000 .
H15 H -0.1761(3) 0.09960(18) 0.22806(14) 0.0407(4) Uiso 1.000000 R
C5 C 1.2346(3) 0.95462(18) 0.22532(14) 0.0301(3) Uani 1.000000 .
H5 H 1.3818(3) 1.01610(18) 0.24691(14) 0.0361(4) Uiso 1.000000 R
C13 C -0.1491(3) 0.40744(18) 0.12428(13) 0.0300(3) Uani 1.000000 .
H13 H -0.2272(3) 0.44626(18) 0.07366(13) 0.0360(4) 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'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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
C1 S9 C8 91.73(7) . . ?
C11 N10 C1 122.86(13) . . ?
H18b N18 H18a 120.0 . . ?
C17 N18 H18a 120.0 . . ?
C17 N18 H18b 120.0 . . ?
C2 C3 C8 114.78(12) . . ?
C4 C3 C8 119.48(13) . . ?
C4 C3 C2 125.69(13) . . ?
C3 C8 S9 113.95(11) . . ?
C7 C8 S9 124.46(12) . . ?
C7 C8 C3 121.59(14) . . ?
C1 C2 C3 106.35(11) . . ?
C17 C2 C3 110.79(11) . . ?
C17 C2 C1 107.46(11) . . ?
C20 C2 C3 111.41(12) . . ?
C20 C2 C1 110.37(12) . . ?
C20 C2 C17 110.31(11) . . ?
N10 C1 S9 127.34(11) . . ?
C2 C1 S9 111.86(10) . . ?
C2 C1 N10 120.81(13) . . ?
N18 C17 O19 122.93(13) . . ?
C2 C17 O19 121.30(13) . . ?
C2 C17 N18 115.75(12) . . ?
C12 C11 N10 122.52(13) . . ?
C16 C11 N10 117.79(13) . . ?
C16 C11 C12 119.51(14) . . ?
H12 C12 C11 119.96(8) . . ?
C13 C12 C11 120.08(14) . . ?
C13 C12 H12 119.96(9) . . ?
H7 C7 C8 120.89(9) . . ?
C6 C7 C8 118.22(14) . . ?
C6 C7 H7 120.89(9) . . ?
H16 C16 C11 119.96(9) . . ?
C15 C16 C11 120.08(15) . . ?
C15 C16 H16 119.96(10) . . ?
C15 C14 H14 120.03(9) . . ?
C13 C14 H14 120.03(10) . . ?
C13 C14 C15 119.94(15) . . ?
H4 C4 C3 120.18(9) . . ?
C5 C4 C3 119.64(14) . . ?
C5 C4 H4 120.18(9) . . ?
H20a C20 C2 109.5 . . ?
H20b C20 C2 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C2 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H6 C6 C7 119.54(9) . . ?
C5 C6 C7 120.91(14) . . ?
C5 C6 H6 119.54(9) . . ?
C14 C15 C16 120.14(15) . . ?
H15 C15 C16 119.93(10) . . ?
H15 C15 C14 119.93(9) . . ?
C6 C5 C4 120.15(14) . . ?
H5 C5 C4 119.92(9) . . ?
H5 C5 C6 119.92(9) . . ?
C14 C13 C12 120.23(15) . . ?
H13 C13 C12 119.89(9) . . ?
H13 C13 C14 119.89(10) . . ?
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
S9 C8 1.7604(15) . ?
S9 C1 1.7786(14) . ?
O19 C17 1.2274(18) . ?
N10 C1 1.2680(19) . ?
N10 C11 1.4183(19) . ?
N18 H18a 0.8800 . ?
N18 H18b 0.8800 . ?
N18 C17 1.3368(19) . ?
C3 C8 1.392(2) . ?
C3 C2 1.5109(19) . ?
C3 C4 1.386(2) . ?
C8 C7 1.390(2) . ?
C2 C1 1.5378(19) . ?
C2 C17 1.5542(19) . ?
C2 C20 1.5416(19) . ?
C11 C12 1.394(2) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C14 C13 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C6 H6 0.9500 . ?
C6 C5 1.389(2) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
