#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:21:23 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284162 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/87/1568768.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_1568768
loop_
_publ_author_name
'Tokareva, Marina A.'
'Pernik, Indrek'
'Messerle, Barbara A.'
'Glukhareva, Tatiana V.'
'Keaveney, Sinead T.'
_publ_section_title
;
 The effect of the C5-substituent on regioselectivity in the
 Rh(i)-catalyzed intermolecular transannulation of 1,2,3-thiadiazoles with
 phenylacetylene
;
_journal_issue                   9
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              2772
_journal_page_last               2782
_journal_paper_doi               10.1039/D3CY00290J
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C17 H21 N O2 S'
_chemical_formula_sum            'C17 H21 N O2 S'
_chemical_formula_weight         303.428
_chemical_name_systematic
'ethyl 2-(cyclopentanecarbonothioyl)-3-phenylbutanoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-11-15 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.380(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7409(1)
_cell_length_b                   7.7066(1)
_cell_length_c                   21.1913(2)
_cell_measurement_reflns_used    14017
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.4090
_cell_measurement_theta_min      4.1570
_cell_volume                     1590.35(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9940
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  43.00   1.00    1.00    --  -40.07  19.00  60.00   48
  2  ω     -5.00  43.00   1.00    1.00    --  -40.07  19.00 -90.00   48
  3  ω     -5.00  43.00   1.00    1.00    --  -40.07  19.00 -30.00   48
  4  ω     -5.00  43.00   1.00    1.00    --  -40.07  19.00-150.00   48
  5  ω     -5.00  43.00   1.00    1.00    --  -40.07  19.00 -60.00   48
  6  ω     -5.00  43.00   1.00    1.00    --  -40.07  19.00-180.00   48
  7  ω    -21.00  37.00   1.00    1.00    --  -40.07  38.00  30.00   58
  8  ω     61.00 131.00   1.00    1.00    --   40.07 178.00  30.00   70
  9  ω     26.00  96.00   1.00    1.00    --   40.07-124.00-165.00   70
 10  ω     58.00 130.00   1.00    1.00    --   40.07-178.00-180.00   72
 11  ω     31.00 109.00   1.00    1.00    --  107.62-112.00  60.00   78
 12  ω     74.00 178.00   1.00    1.00    --  107.62  30.00 -30.00  104
 13  ω     31.00 109.00   1.00    1.00    --  107.62-112.00-120.00   78
 14  ω     31.00  72.00   1.00    1.00    --  107.62 -45.00 -60.00   41
 15  ω     31.00 109.00   1.00    1.00    --  107.62-112.00-150.00   78
 16  ω     31.00  72.00   1.00    1.00    --  107.62 -45.00-150.00   41
 17  ω     28.00  57.00   1.00    1.00    --  107.62 -30.00   0.00   29
 18  ω     31.00 109.00   1.00    1.00    --  107.62-112.00   0.00   78
 19  ω     31.00  72.00   1.00    1.00    --  107.62 -45.00-180.00   41
 20  ω     28.00  57.00   1.00    1.00    --  107.62 -30.00  30.00   29
 21  ω     23.00 106.00   1.00    1.00    --  107.62 -95.00  90.00   83
 22  ω    104.00 166.00   1.00    1.00    --  107.62 112.00-120.00   62
 23  ω     28.00  57.00   1.00    1.00    --  107.62 -30.00 150.00   29
 24  ω     31.00  72.00   1.00    1.00    --  107.62 -45.00  90.00   41
 25  ω     30.00 178.00   1.00    1.00    --  107.62  15.00  60.00  148
 26  ω     61.00 143.00   1.00    1.00    --  107.62 178.00  30.00   82
 27  ω     76.00 176.00   1.00    1.00    --  107.62  61.00-180.00  100
 28  ω     76.00 176.00   1.00    1.00    --  107.62  61.00  30.00  100
 29  ω     76.00 176.00   1.00    1.00    --  107.62  61.00 -90.00  100
 30  ω     76.00 176.00   1.00    1.00    --  107.62  61.00-150.00  100
 31  ω     76.00 176.00   1.00    1.00    --  107.62  61.00  90.00  100
 32  ω     78.00 178.00   1.00    1.00    --  107.62  45.00  90.00  100
 33  ω     76.00 176.00   1.00    1.00    --  107.62  61.00 -30.00  100
 34  ω     76.00 160.00   1.00    1.00    --  107.62  61.00-120.00   84
 35  ω     76.00 176.00   1.00    1.00    --  107.62  61.00 150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1228095000
_diffrn_orient_matrix_UB_12      0.0377771000
_diffrn_orient_matrix_UB_13      -0.0423490000
_diffrn_orient_matrix_UB_21      -0.0890517000
_diffrn_orient_matrix_UB_22      -0.0441771000
_diffrn_orient_matrix_UB_23      -0.0589076000
_diffrn_orient_matrix_UB_31      -0.0446623000
_diffrn_orient_matrix_UB_32      0.1912933000
_diffrn_orient_matrix_UB_33      -0.0052203000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9940
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21419
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9940
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         72.42
_diffrn_reflns_theta_min         4.17
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             651.148
_exptl_crystal_recrystallization_method
'recrystallation from ethyl acetate and hexane'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.3457
_refine_diff_density_min         -0.1819
_refine_diff_density_rms         0.0493
_refine_ls_d_res_high            0.8087
_refine_ls_d_res_low             10.5926
_refine_ls_goodness_of_fit_ref   1.0802
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0802
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -12
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              -9
_reflns_number_gt                2933
_reflns_number_total             3130
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cy00290j2.cif
_cod_data_source_block           bam22_s2580_sn950
_cod_depositor_comments
'Adding full bibliography for 1568765--1568768.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1568768
_chemical_oxdiff_formula         C17H18N1S1O3
_chemical_oxdiff_usercomment     10b
_reflns_odcompleteness_completeness 100.00
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C16(H16a,H16b), C12(H12a,H12b), C14(H14a,H14b), C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C17(H17a,H17b,H17c)
;
_olex2_submission_original_sample_id BAM_10a
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.696
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-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_refinement_flags_posn
S1 S 1.01774(3) 0.68287(4) 0.577586(13) 0.02315(15) Uani 1.000000 .
O2 O 0.69185(9) 0.78929(11) 0.69582(4) 0.0205(2) Uani 1.000000 .
O1 O 0.71761(12) 0.98523(12) 0.61864(4) 0.0369(3) Uani 1.000000 .
N1 N 0.82586(9) 0.77056(14) 0.49286(4) 0.0195(2) Uani 1.000000 .
C7 C 0.66499(11) 0.54025(15) 0.59271(5) 0.0178(2) Uani 1.000000 .
C6 C 0.54480(11) 0.51672(15) 0.63466(5) 0.0182(3) Uani 1.000000 .
C9 C 0.74068(11) 0.68582(14) 0.59404(5) 0.0176(3) Uani 1.000000 .
C15 C 0.71597(12) 0.83652(15) 0.63649(5) 0.0203(3) Uani 1.000000 .
C10 C 0.85756(11) 0.71610(14) 0.55027(5) 0.0172(2) Uani 1.000000 .
C1 C 0.43540(12) 0.63314(17) 0.63158(5) 0.0221(3) Uani 1.000000 .
C11 C 0.92998(12) 0.80686(16) 0.44491(5) 0.0215(3) Uani 1.000000 .
C8 C 0.69260(11) 0.39352(16) 0.54785(6) 0.0230(3) Uani 1.000000 .
C5 C 0.53983(12) 0.37848(17) 0.67664(6) 0.0244(3) Uani 1.000000 .
C16 C 0.64329(13) 0.92469(16) 0.73752(5) 0.0254(3) Uani 1.000000 .
C3 C 0.32312(12) 0.48030(18) 0.71474(6) 0.0287(3) Uani 1.000000 .
C12 C 0.84533(13) 0.86914(18) 0.38772(5) 0.0279(3) Uani 1.000000 .
C2 C 0.32450(12) 0.61479(18) 0.67116(6) 0.0269(3) Uani 1.000000 .
C14 C 0.68646(13) 0.81453(17) 0.46889(6) 0.0255(3) Uani 1.000000 .
C17 C 0.57906(14) 0.83533(18) 0.79270(6) 0.0283(3) Uani 1.000000 .
C13 C 0.71517(13) 0.94232(18) 0.41620(6) 0.0283(3) Uani 1.000000 .
C4 C 0.43048(13) 0.36264(19) 0.71755(6) 0.0302(3) Uani 1.000000 .
H5 H 0.61119(12) 0.29443(17) 0.67748(6) 0.0293(3) Uiso 1.000000 R
H4 H 0.42968(13) 0.27080(19) 0.74745(6) 0.0363(4) Uiso 1.000000 R
H3 H 0.24863(12) 0.46905(18) 0.74257(6) 0.0345(4) Uiso 1.000000 R
H2 H 0.24991(12) 0.69405(18) 0.66839(6) 0.0322(3) Uiso 1.000000 R
H1 H 0.43659(12) 0.72604(17) 0.60213(5) 0.0265(3) Uiso 1.000000 R
H11a H 0.99486(12) 0.89780(16) 0.45976(5) 0.0258(3) Uiso 1.000000 R
H11b H 0.98233(12) 0.70077(16) 0.43476(5) 0.0258(3) Uiso 1.000000 R
H8a H 0.7047(10) 0.2855(3) 0.57172(7) 0.0344(4) Uiso 1.000000 GR
H8b H 0.6148(5) 0.3813(8) 0.5180(3) 0.0344(4) Uiso 1.000000 GR
H8c H 0.7762(6) 0.4183(6) 0.5247(3) 0.0344(4) Uiso 1.000000 GR
H16a H 0.72077(13) 0.99869(16) 0.75219(5) 0.0305(3) Uiso 1.000000 R
H16b H 0.57479(13) 0.99868(16) 0.71514(5) 0.0305(3) Uiso 1.000000 R
H12a H 0.89503(13) 0.95987(18) 0.36435(5) 0.0335(3) Uiso 1.000000 R
H12b H 0.82352(13) 0.77172(18) 0.35873(5) 0.0335(3) Uiso 1.000000 R
H14a H 0.63784(13) 0.71044(17) 0.45253(6) 0.0306(4) Uiso 1.000000 R
H14b H 0.63123(13) 0.86879(17) 0.50218(6) 0.0306(4) Uiso 1.000000 R
H17a H 0.5014(7) 0.7646(11) 0.77763(9) 0.0424(5) Uiso 1.000000 GR
H17b H 0.6474(3) 0.7607(11) 0.8139(3) 0.0424(5) Uiso 1.000000 GR
H17c H 0.5466(10) 0.92254(18) 0.8225(3) 0.0424(5) Uiso 1.000000 GR
H13a H 0.73071(13) 1.06073(18) 0.43302(6) 0.0340(3) Uiso 1.000000 R
H13b H 0.63855(13) 0.94531(18) 0.38467(6) 0.0340(3) 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
C16 O2 C15 116.36(9) . . ?
C11 N1 C10 123.06(10) . . ?
C14 N1 C10 125.72(9) . . ?
C14 N1 C11 111.10(9) . . ?
C9 C7 C6 121.70(10) . . ?
C8 C7 C6 115.97(9) . . ?
C8 C7 C9 122.31(10) . . ?
C1 C6 C7 120.14(10) . . ?
C5 C6 C7 120.83(10) . . ?
C5 C6 C1 119.03(10) . . ?
C15 C9 C7 124.52(10) . . ?
C10 C9 C7 122.70(10) . . ?
C10 C9 C15 112.74(9) . . ?
O1 C15 O2 123.91(11) . . ?
C9 C15 O2 112.96(9) . . ?
C9 C15 O1 123.13(10) . . ?
N1 C10 S1 124.42(9) . . ?
C9 C10 S1 118.49(8) . . ?
C9 C10 N1 117.08(10) . . ?
C2 C1 C6 120.70(11) . . ?
C12 C11 N1 103.80(9) . . ?
C4 C5 C6 120.26(11) . . ?
C17 C16 O2 106.92(10) . . ?
C4 C3 C2 119.88(11) . . ?
C13 C12 C11 103.91(9) . . ?
C3 C2 C1 119.81(11) . . ?
C13 C14 N1 102.55(9) . . ?
C14 C13 C12 102.74(10) . . ?
C3 C4 C5 120.22(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 C10 1.6709(11) . ?
O2 C15 1.3351(14) . ?
O2 C16 1.4539(14) . ?
O1 C15 1.2071(15) . ?
N1 C10 1.3165(15) . ?
N1 C11 1.4796(14) . ?
N1 C14 1.4777(15) . ?
C7 C6 1.4980(14) . ?
C7 C9 1.3424(16) . ?
C7 C8 1.5057(15) . ?
C6 C1 1.3933(16) . ?
C6 C5 1.3895(17) . ?
C9 C15 1.4921(15) . ?
C9 C10 1.5040(14) . ?
C1 C2 1.3907(16) . ?
C11 C12 1.5266(16) . ?
C5 C4 1.3949(16) . ?
C16 C17 1.5061(17) . ?
C3 C2 1.3884(19) . ?
C3 C4 1.384(2) . ?
C12 C13 1.5253(17) . ?
C14 C13 1.5199(16) . ?
