# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bam22_s2419_sn917
_database_code_depnum_ccdc_archive 'CCDC 2219742'
loop_
_audit_author_name
_audit_author_address
'Indrek pernik'
;The University of Sydney
Australia
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 4-phenyl-2-(pyrrolidin-1-yl)thiophene-3-carboxylate'
_chemical_formula_moiety         'C17 H19 N O2 S'
_chemical_formula_sum            'C17 H19 N O2 S'
_chemical_formula_weight         301.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H20 N5 O2 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8925(4)
_cell_length_b                   7.8461(2)
_cell_length_c                   15.2747(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.851(3)
_cell_angle_gamma                90
_cell_volume                     1517.50(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11358
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.4400
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.922
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 2 0.1403
1 -5 -2 0.1403
1 0 9 0.0755
-1 0 -9 0.0465
-8 0 0 0.1050
8 0 0 0.1050
-1 -1 -1 0.1136
3 0 -10 0.0566
-5 -1 9 0.1141

_exptl_crystal_preparation       .
_exptl_crystal_recrystallization_method .
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.122
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9890 4.9934 1.9923 -0.0153 0.2541 0.9706
0.9890 -4.9934 -1.9923 0.0153 -0.2541 -0.9706
1.0014 -0.0000 9.0089 0.1269 -0.8635 0.3906
-1.0014 0.0000 -9.0089 -0.1269 0.8635 -0.3906
-8.0041 0.0025 -0.0014 -0.9529 0.2008 0.0143
8.0041 -0.0025 0.0014 0.9529 -0.2008 -0.0143
-1.0029 -0.9983 -0.9993 -0.1404 0.0352 -0.2181
2.6154 0.2662 -9.8139 0.3084 0.8699 -0.3850
-4.8665 -1.0366 8.7492 -0.5928 -0.7784 0.2064

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13345
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.564
_diffrn_reflns_theta_min         6.266
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -131.00  51.00   1.00    2.50    --  -40.07   0.00  90.00  182
  2  ω     61.00 131.00   1.00    2.50    --   40.07 178.00-180.00   70
  3  ω     61.00 131.00   1.00    2.50    --   40.07 178.00 -30.00   70
  4  ω     61.00 131.00   1.00    2.50    --   40.07 178.00  90.00   70
  5  ω     58.00 130.00   1.00    2.50    --   40.07-178.00 -90.00   72
  6  ω     28.00  57.00   1.00   10.00    --  107.94 -30.00  90.00   29
  7  ω     28.00  57.00   1.00   10.00    --  107.94 -30.00-150.00   29
  8  ω     32.00  93.00   1.00   10.00    --  107.94 -61.00 -60.00   61
  9  ω     29.00 109.00   1.00   10.00    --  107.94-112.00 -60.00   80
 10  ω     31.00  72.00   1.00   10.00    --  107.94 -45.00   0.00   41
 11  ω     28.00  57.00   1.00   10.00    --  107.94 -30.00  60.00   29
 12  ω     32.00  93.00   1.00   10.00    --  107.94 -61.00   0.00   61
 13  ω     28.00  57.00   1.00   10.00    --  107.94 -30.00   0.00   29
 14  ω     29.00 109.00   1.00   10.00    --  107.94-112.00  30.00   80
 15  ω     28.00  57.00   1.00   10.00    --  107.94 -30.00 -30.00   29
 16  ω     74.00 178.00   1.00   10.00    --  107.94  30.00 -30.00  104
 17  ω     74.00 178.00   1.00   10.00    --  107.94  30.00-120.00  104
 18  ω     28.00  57.00   1.00   10.00    --  107.94 -30.00  30.00   29
 19  ω     23.00 106.00   1.00   10.00    --  107.94 -95.00-180.00   83
 20  ω     32.00  93.00   1.00   10.00    --  107.94 -61.00  30.00   61
 21  ω     31.00  72.00   1.00   10.00    --  107.94 -45.00-180.00   41
 22  ω     26.00 126.00   1.00   10.00    --  107.94 -77.00-150.00  100
 23  ω     31.00  72.00   1.00   10.00    --  107.94 -45.00 -60.00   41
 24  ω     29.00 109.00   1.00   10.00    --  107.94-112.00 150.00   80
 25  ω   -116.00  -9.00   1.00    2.50    --  -40.07 -57.00 -90.00  107
 26  ω   -116.00  -9.00   1.00    2.50    --  -40.07 -57.00-180.00  107
 27  ω   -116.00  -9.00   1.00    2.50    --  -40.07 -57.00   0.00  107
 28  ω    -22.00  37.00   1.00    2.50    --  -40.07  38.00-120.00   59
 29  ω   -116.00  -9.00   1.00    2.50    --  -40.07 -57.00  90.00  107
 30  ω     76.00 178.00   1.00   10.00    --  107.94  61.00 150.00  102
 31  ω     31.00 178.00   1.00   10.00    --  107.94  15.00 120.00  147
 32  ω     76.00 178.00   1.00   10.00    --  107.94  61.00  90.00  102
 33  ω     79.00 178.00   1.00   10.00    --  107.94  45.00 -90.00   99
 34  ω     76.00 157.00   1.00   10.00    --  107.94  61.00-180.00   81
 35  ω     79.00 178.00   1.00   10.00    --  107.94  45.00   0.00   99
;
_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      0.1190548000
_diffrn_orient_matrix_UB_12      0.0201793000
_diffrn_orient_matrix_UB_13      0.0008521000
_diffrn_orient_matrix_UB_21      -0.0250491000
_diffrn_orient_matrix_UB_22      0.0830523000
_diffrn_orient_matrix_UB_23      -0.0930615000
_diffrn_orient_matrix_UB_31      -0.0017460000
_diffrn_orient_matrix_UB_32      0.1766447000
_diffrn_orient_matrix_UB_33      0.0435522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2827
_reflns_number_total             2926
_reflns_odcompleteness_completeness 98.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+1.4490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          ?
_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:
 C3(H3A,H3B), C8(H8A,H8B), C4(H4A,H4B), C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C17(H17), C16(H16), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51578(3) 0.35371(5) 0.09665(2) 0.01661(13) Uani 1 1 d . . . . .
O2 O 0.80280(9) 0.43231(14) 0.34406(7) 0.0154(3) Uani 1 1 d . . . . .
O1 O 0.71604(9) 0.19769(14) 0.37634(7) 0.0169(3) Uani 1 1 d . . . . .
N1 N 0.48476(11) 0.30853(17) 0.26303(8) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.71603(13) 0.35603(18) 0.15539(10) 0.0133(3) Uani 1 1 d . . . . .
C6 C 0.66834(13) 0.32831(18) 0.23268(9) 0.0123(3) Uani 1 1 d . . . . .
C11 C 0.64334(14) 0.36841(19) 0.07851(10) 0.0159(3) Uani 1 1 d . . . . .
H11 H 0.660958 0.383450 0.021351 0.019 Uiso 1 1 calc R U . . .
C7 C 0.72929(12) 0.30869(19) 0.32428(10) 0.0121(3) Uani 1 1 d . . . . .
C13 C 0.90004(14) 0.2404(2) 0.19983(10) 0.0190(3) Uani 1 1 d . . . . .
H13 H 0.874109 0.153936 0.233605 0.023 Uiso 1 1 calc R U . . .
C3 C 0.39609(13) 0.3954(2) 0.37763(11) 0.0191(3) Uani 1 1 d . . . . .
H3A H 0.384497 0.520096 0.373750 0.023 Uiso 1 1 calc R U . . .
H3B H 0.388345 0.355798 0.437603 0.023 Uiso 1 1 calc R U . . .
C8 C 0.86696(13) 0.4279(2) 0.43308(10) 0.0178(3) Uani 1 1 d . . . . .
H8A H 0.937681 0.475808 0.431785 0.021 Uiso 1 1 calc R U . . .
H8B H 0.876120 0.308378 0.453938 0.021 Uiso 1 1 calc R U . . .
C5 C 0.55857(13) 0.32322(19) 0.21120(10) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.83069(13) 0.36158(19) 0.15499(10) 0.0145(3) Uani 1 1 d . . . . .
C4 C 0.50448(13) 0.3491(2) 0.35860(10) 0.0165(3) Uani 1 1 d . . . . .
H4A H 0.554026 0.446127 0.372007 0.020 Uiso 1 1 calc R U . . .
H4B H 0.534291 0.249519 0.394538 0.020 Uiso 1 1 calc R U . . .
C17 C 0.87127(15) 0.4886(2) 0.10677(10) 0.0213(4) Uani 1 1 d . . . . .
H17 H 0.825196 0.572432 0.075854 0.026 Uiso 1 1 calc R U . . .
C1 C 0.37150(13) 0.3165(2) 0.22412(11) 0.0194(3) Uani 1 1 d . . . . .
H1A H 0.350357 0.220954 0.182243 0.023 Uiso 1 1 calc R U . . .
H1B H 0.353324 0.425593 0.192332 0.023 Uiso 1 1 calc R U . . .
C16 C 0.97740(16) 0.4937(3) 0.10357(12) 0.0284(4) Uani 1 1 d . . . . .
H16 H 1.003893 0.581682 0.071125 0.034 Uiso 1 1 calc R U . . .
C15 C 1.04555(16) 0.3718(3) 0.14721(12) 0.0305(5) Uani 1 1 d . . . . .
H15 H 1.118417 0.375042 0.144062 0.037 Uiso 1 1 calc R U . . .
C2 C 0.31913(14) 0.3026(2) 0.30503(12) 0.0208(4) Uani 1 1 d . . . . .
H2A H 0.310689 0.181977 0.321349 0.025 Uiso 1 1 calc R U . . .
H2B H 0.249050 0.358546 0.293962 0.025 Uiso 1 1 calc R U . . .
C9 C 0.81466(16) 0.5296(2) 0.49626(11) 0.0246(4) Uani 1 1 d . . . . .
H9A H 0.800387 0.645293 0.472872 0.037 Uiso 1 1 calc R U . . .
H9B H 0.861476 0.535006 0.554711 0.037 Uiso 1 1 calc R U . . .
H9C H 0.748072 0.474778 0.502302 0.037 Uiso 1 1 calc R U . . .
C14 C 1.00719(15) 0.2447(3) 0.19560(11) 0.0266(4) Uani 1 1 d . . . . .
H14 H 1.053747 0.160775 0.225807 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C11 1.7223(17) . ?
S1 C5 1.7491(15) . ?
O2 C7 1.3499(19) . ?
O2 C8 1.4529(18) . ?
O1 C7 1.2129(19) . ?
N1 C5 1.353(2) . ?
N1 C4 1.4689(19) . ?
N1 C1 1.470(2) . ?
C10 C6 1.447(2) . ?
C10 C11 1.361(2) . ?
C10 C12 1.480(2) . ?
C6 C7 1.478(2) . ?
C6 C5 1.392(2) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.394(2) . ?
C13 C14 1.395(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(2) . ?
C3 C2 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.506(2) . ?
C12 C17 1.398(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C16 1.379(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.520(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C14 H14 0.9500 . ?

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
C11 S1 C5 92.24(8) . . ?
C7 O2 C8 116.37(12) . . ?
C5 N1 C4 123.64(14) . . ?
C5 N1 C1 120.95(13) . . ?
C4 N1 C1 111.43(13) . . ?
C6 C10 C12 125.88(14) . . ?
C11 C10 C6 112.67(15) . . ?
C11 C10 C12 121.36(14) . . ?
C10 C6 C7 123.80(14) . . ?
C5 C6 C10 112.42(13) . . ?
C5 C6 C7 123.78(14) . . ?
S1 C11 H11 123.8 . . ?
C10 C11 S1 112.31(12) . . ?
C10 C11 H11 123.8 . . ?
O2 C7 C6 111.26(12) . . ?
O1 C7 O2 123.29(14) . . ?
O1 C7 C6 125.45(14) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.63(16) . . ?
C14 C13 H13 119.7 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C4 C3 C2 104.00(13) . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
O2 C8 H8A 109.7 . . ?
O2 C8 H8B 109.7 . . ?
O2 C8 C9 110.01(13) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
N1 C5 S1 118.23(12) . . ?
N1 C5 C6 131.35(14) . . ?
C6 C5 S1 110.32(11) . . ?
C13 C12 C10 121.78(14) . . ?
C13 C12 C17 118.45(16) . . ?
C17 C12 C10 119.75(15) . . ?
N1 C4 C3 104.35(13) . . ?
N1 C4 H4A 110.9 . . ?
N1 C4 H4B 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.76(17) . . ?
C16 C17 H17 119.6 . . ?
N1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
N1 C1 C2 103.16(13) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C17 C16 H16 119.7 . . ?
C17 C16 C15 120.52(17) . . ?
C15 C16 H16 119.7 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.77(18) . . ?
C14 C15 H15 120.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 C3 103.24(13) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.86(18) . . ?
C15 C14 H14 120.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 34.02(16) . . . . ?
C10 C6 C7 O2 48.26(19) . . . . ?
C10 C6 C7 O1 -132.16(17) . . . . ?
C10 C6 C5 S1 -0.33(16) . . . . ?
C10 C6 C5 N1 -176.39(15) . . . . ?
C10 C12 C17 C16 -178.33(15) . . . . ?
C6 C10 C11 S1 1.82(17) . . . . ?
C6 C10 C12 C13 45.8(2) . . . . ?
C6 C10 C12 C17 -135.87(16) . . . . ?
C11 S1 C5 N1 177.78(12) . . . . ?
C11 S1 C5 C6 1.13(12) . . . . ?
C11 C10 C6 C7 179.41(14) . . . . ?
C11 C10 C6 C5 -0.95(18) . . . . ?
C11 C10 C12 C13 -130.61(16) . . . . ?
C11 C10 C12 C17 47.8(2) . . . . ?
C7 O2 C8 C9 -89.46(17) . . . . ?
C7 C6 C5 S1 179.31(12) . . . . ?
C7 C6 C5 N1 3.2(3) . . . . ?
C13 C12 C17 C16 0.1(2) . . . . ?
C8 O2 C7 O1 -0.4(2) . . . . ?
C8 O2 C7 C6 179.17(12) . . . . ?
C5 S1 C11 C10 -1.71(12) . . . . ?
C5 N1 C4 C3 154.11(14) . . . . ?
C5 N1 C1 C2 -177.62(13) . . . . ?
C5 C6 C7 O2 -131.33(15) . . . . ?
C5 C6 C7 O1 48.3(2) . . . . ?
C12 C10 C6 C7 2.8(2) . . . . ?
C12 C10 C6 C5 -177.60(14) . . . . ?
C12 C10 C11 S1 178.63(11) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C17 C16 C15 0.8(3) . . . . ?
C4 N1 C5 S1 -155.14(12) . . . . ?
C4 N1 C5 C6 20.7(3) . . . . ?
C4 N1 C1 C2 -19.28(17) . . . . ?
C4 C3 C2 C1 -36.71(16) . . . . ?
C17 C16 C15 C14 -0.9(3) . . . . ?
C1 N1 C5 S1 0.5(2) . . . . ?
C1 N1 C5 C6 176.31(15) . . . . ?
C1 N1 C4 C3 -3.54(17) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C2 C3 C4 N1 24.90(16) . . . . ?
C14 C13 C12 C10 177.54(14) . . . . ?
C14 C13 C12 C17 -0.8(2) . . . . ?

_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 3.712
_oxdiff_exptl_absorpt_empirical_full_min 0.604
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bam22_s2609_sn981
_database_code_depnum_ccdc_archive 'CCDC 2219745'
loop_
_audit_author_name
_audit_author_address
'Indrek pernik'
;The University of Sydney
Australia
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 5-(4-nitrophenyl)-3-phenylisothiazole-4-carboxylate'
_chemical_formula_moiety         '0.5(C18 H14 N2 O4 S)'
_chemical_formula_sum            'C9 H7 N O2 S0.50'
_chemical_formula_weight         177.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H14 N2 O4 S1'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8717(4)
_cell_length_b                   8.9788(4)
_cell_length_c                   10.5747(4)
_cell_angle_alpha                100.966(4)
_cell_angle_beta                 100.107(4)
_cell_angle_gamma                93.879(4)
_cell_volume                     809.68(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8921
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      29.1690
_cell_measurement_theta_min      2.3210
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -13 2 0.1033
0 13 -2 0.1033
10 -2 7 0.1756
-10 2 -7 0.1756
-2 -1 15 0.1434
2 1 -15 0.1434
11 -1 -8 0.1393
-10 0 10 0.1317
4 11 2 0.1151

_exptl_crystal_preparation       
'transannulation of ethyl 5-(4-nitrophenyl)-1,2,3-thiadiazole-4-carboxylate with benzonitrile'
_exptl_crystal_recrystallization_method 'n--hexane solution at rt'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0780 -12.6174 2.2657 0.1281 0.9917 -0.0066
-0.0780 12.6174 -2.2657 -0.1281 -0.9917 0.0066
9.6009 -1.9136 7.3879 0.0016 0.0656 -0.9978
-9.6009 1.9136 -7.3879 -0.0016 -0.0656 0.9978
-1.9385 -0.5171 14.7315 -0.8557 0.1072 -0.5063
1.9385 0.5171 -14.7315 0.8557 -0.1072 0.5063
11.4946 -0.5361 -8.1202 0.8805 -0.1108 -0.4608
-10.3015 0.3199 10.3813 -0.9530 0.1213 0.2775
3.5742 10.7047 2.4980 -0.2094 -0.8682 -0.4498

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.504
_diffrn_reflns_theta_min         1.999
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  21.00   1.00    2.00    --  -11.94  77.00 120.00   68
  2  ω    -15.00  30.00   1.00    2.00    --  -11.94 -99.00 -60.00   45
  3  ω    -68.00  26.00   1.00    2.00    --   14.91 -19.00 150.00   94
  4  ω    -14.00  92.00   1.00    2.00    --   14.91  38.00 -30.00  106
  5  ω     37.00 105.00   1.00    2.00    --   14.91-178.00-180.00   68
  6  ω    -36.00 -11.00   1.00    2.00    --  -11.94 -73.00 -15.00   25
  7  ω    -42.00  23.00   1.00    2.00    --  -11.94 -77.00  30.00   65
  8  ω    -47.00  21.00   1.00    2.00    --  -11.94  77.00 -90.00   68
  9  ω    -47.00  21.00   1.00    2.00    --  -11.94  77.00 -60.00   68
 10  ω    -42.00  50.00   1.00    2.00    --   14.91 -77.00-120.00   92
 11  ω    -15.00  57.00   1.00    2.00    --   14.91 -99.00  30.00   72
 12  ω    -14.00  92.00   1.00    2.00    --   14.91  38.00-150.00  106
;
_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      0.0376761000
_diffrn_orient_matrix_UB_12      -0.0195849000
_diffrn_orient_matrix_UB_13      -0.0538129000
_diffrn_orient_matrix_UB_21      -0.0111070000
_diffrn_orient_matrix_UB_22      -0.0781176000
_diffrn_orient_matrix_UB_23      0.0030736000
_diffrn_orient_matrix_UB_31      -0.0715859000
_diffrn_orient_matrix_UB_32      -0.0078313000
_diffrn_orient_matrix_UB_33      -0.0440648000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3468
_reflns_number_total             4052
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.3207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0905
_refine_special_details          ?
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C18(H18), C14(H14), C4(H4), C17(H17), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.81747(4) 0.66014(4) 0.60142(3) 0.02528(10) Uani 1 1 d . . . . .
O4 O 0.61183(11) 0.40139(11) 0.19214(10) 0.0290(2) Uani 1 1 d . . . . .
O3 O 0.82729(13) 0.28701(14) 0.21200(12) 0.0449(3) Uani 1 1 d . . . . .
O2 O 0.59392(15) -0.10917(13) 0.69708(13) 0.0448(3) Uani 1 1 d . . . . .
N2 N 0.88223(14) 0.75040(13) 0.49827(11) 0.0254(3) Uani 1 1 d . . . . .
O1 O 0.45298(16) 0.04391(14) 0.79294(13) 0.0472(3) Uani 1 1 d . . . . .
N1 N 0.54365(14) 0.01448(14) 0.71922(12) 0.0285(3) Uani 1 1 d . . . . .
C6 C 0.69549(15) 0.36106(15) 0.53837(13) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.79981(15) 0.50567(15) 0.37437(13) 0.0210(3) Uani 1 1 d . . . . .
C13 C 0.92648(16) 0.71835(15) 0.27741(13) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.75242(15) 0.38474(15) 0.25131(13) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.59268(16) 0.13304(15) 0.65253(13) 0.0235(3) Uani 1 1 d . . . . .
C12 C 0.86771(15) 0.65705(15) 0.38142(13) 0.0222(3) Uani 1 1 d . . . . .
C7 C 0.76461(15) 0.49009(15) 0.49319(13) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.59169(15) 0.38851(16) 0.62320(13) 0.0237(3) Uani 1 1 d . . . . .
H1 H 0.557011 0.486723 0.641556 0.028 Uiso 1 1 calc R U . . .
C2 C 0.53880(16) 0.27462(16) 0.68077(14) 0.0249(3) Uani 1 1 d . . . . .
H2 H 0.467613 0.292791 0.738016 0.030 Uiso 1 1 calc R U . . .
C5 C 0.74302(16) 0.21491(15) 0.50831(14) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.810044 0.194388 0.447659 0.029 Uiso 1 1 calc R U . . .
C18 C 0.99920(17) 0.62865(16) 0.18853(13) 0.0262(3) Uani 1 1 d . . . . .
H18 H 1.003591 0.523384 0.189259 0.031 Uiso 1 1 calc R U . . .
C14 C 0.92103(17) 0.87309(16) 0.27436(14) 0.0279(3) Uani 1 1 d . . . . .
H14 H 0.871593 0.935366 0.334287 0.033 Uiso 1 1 calc R U . . .
C4 C 0.69262(16) 0.10045(16) 0.56670(14) 0.0252(3) Uani 1 1 d . . . . .
H4 H 0.725927 0.001638 0.548238 0.030 Uiso 1 1 calc R U . . .
C17 C 1.06505(18) 0.69254(17) 0.09914(14) 0.0304(3) Uani 1 1 d . . . . .
H17 H 1.114381 0.630748 0.038812 0.036 Uiso 1 1 calc R U . . .
C10 C 0.54399(17) 0.28738(17) 0.07379(14) 0.0288(3) Uani 1 1 d . . . . .
H10A H 0.555281 0.183191 0.089707 0.035 Uiso 1 1 calc R U . . .
H10B H 0.595457 0.300950 0.000310 0.035 Uiso 1 1 calc R U . . .
C16 C 1.05949(19) 0.84622(18) 0.09708(15) 0.0329(3) Uani 1 1 d . . . . .
H16 H 1.105147 0.889608 0.035809 0.040 Uiso 1 1 calc R U . . .
C15 C 0.98699(19) 0.93602(17) 0.18487(15) 0.0324(3) Uani 1 1 d . . . . .
H15 H 0.982610 1.041150 0.183534 0.039 Uiso 1 1 calc R U . . .
C11 C 0.37687(19) 0.3113(2) 0.04187(17) 0.0405(4) Uani 1 1 d . . . . .
H11A H 0.326767 0.238169 -0.038066 0.061 Uiso 1 1 calc R U . . .
H11B H 0.367566 0.415373 0.028003 0.061 Uiso 1 1 calc R U . . .
H11C H 0.327174 0.295853 0.114816 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N2 1.6340(13) . ?
S1 C7 1.7062(13) . ?
O4 C9 1.3253(16) . ?
O4 C10 1.4633(16) . ?
O3 C9 1.1921(17) . ?
O2 N1 1.2210(16) . ?
N2 C12 1.3347(17) . ?
O1 N1 1.2227(17) . ?
N1 C3 1.4665(18) . ?
C6 C7 1.4710(19) . ?
C6 C1 1.396(2) . ?
C6 C5 1.4014(19) . ?
C8 C9 1.5026(18) . ?
C8 C12 1.4320(19) . ?
C8 C7 1.3764(19) . ?
C13 C12 1.476(2) . ?
C13 C18 1.394(2) . ?
C13 C14 1.3998(19) . ?
C3 C2 1.3862(19) . ?
C3 C4 1.383(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(2) . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.383(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.385(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C4 H4 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.388(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.501(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
N2 S1 C7 95.93(6) . . ?
C9 O4 C10 116.79(11) . . ?
C12 N2 S1 110.14(10) . . ?
O2 N1 O1 123.35(13) . . ?
O2 N1 C3 118.36(13) . . ?
O1 N1 C3 118.29(12) . . ?
C1 C6 C7 118.97(12) . . ?
C1 C6 C5 119.53(13) . . ?
C5 C6 C7 121.20(13) . . ?
C12 C8 C9 125.46(12) . . ?
C7 C8 C9 123.20(12) . . ?
C7 C8 C12 110.86(12) . . ?
C18 C13 C12 121.39(12) . . ?
C18 C13 C14 118.93(13) . . ?
C14 C13 C12 119.45(13) . . ?
O4 C9 C8 109.53(11) . . ?
O3 C9 O4 124.33(12) . . ?
O3 C9 C8 126.14(12) . . ?
C2 C3 N1 118.17(13) . . ?
C4 C3 N1 118.99(12) . . ?
C4 C3 C2 122.82(13) . . ?
N2 C12 C8 114.71(13) . . ?
N2 C12 C13 117.43(12) . . ?
C8 C12 C13 127.83(12) . . ?
C6 C7 S1 118.88(10) . . ?
C8 C7 S1 108.36(10) . . ?
C8 C7 C6 132.76(12) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.82(13) . . ?
C2 C1 H1 119.6 . . ?
C3 C2 H2 121.0 . . ?
C1 C2 C3 118.03(13) . . ?
C1 C2 H2 121.0 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.18(13) . . ?
C4 C5 H5 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.20(13) . . ?
C17 C18 H18 119.9 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.54(14) . . ?
C15 C14 H14 119.7 . . ?
C3 C4 C5 118.54(13) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.47(15) . . ?
C16 C17 H17 119.8 . . ?
O4 C10 H10A 110.4 . . ?
O4 C10 H10B 110.4 . . ?
O4 C10 C11 106.54(12) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
C17 C16 H16 120.2 . . ?
C15 C16 C17 119.66(15) . . ?
C15 C16 H16 120.2 . . ?
C14 C15 C16 120.20(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C12 C8 0.54(15) . . . . ?
S1 N2 C12 C13 -177.62(9) . . . . ?
O2 N1 C3 C2 -178.20(13) . . . . ?
O2 N1 C3 C4 0.47(19) . . . . ?
N2 S1 C7 C6 179.97(10) . . . . ?
N2 S1 C7 C8 0.32(10) . . . . ?
O1 N1 C3 C2 2.70(19) . . . . ?
O1 N1 C3 C4 -178.63(13) . . . . ?
N1 C3 C2 C1 176.59(12) . . . . ?
N1 C3 C4 C5 -177.45(12) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C13 C18 C17 C16 0.0(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C9 O4 C10 C11 168.61(13) . . . . ?
C9 C8 C12 N2 171.91(12) . . . . ?
C9 C8 C12 C13 -10.2(2) . . . . ?
C9 C8 C7 S1 -172.49(10) . . . . ?
C9 C8 C7 C6 7.9(2) . . . . ?
C12 C8 C9 O4 -85.12(16) . . . . ?
C12 C8 C9 O3 95.60(19) . . . . ?
C12 C8 C7 S1 -0.07(14) . . . . ?
C12 C8 C7 C6 -179.64(13) . . . . ?
C12 C13 C18 C17 -174.41(12) . . . . ?
C12 C13 C14 C15 174.52(13) . . . . ?
C7 S1 N2 C12 -0.50(10) . . . . ?
C7 C6 C1 C2 -171.94(12) . . . . ?
C7 C6 C5 C4 170.91(12) . . . . ?
C7 C8 C9 O4 86.18(15) . . . . ?
C7 C8 C9 O3 -93.10(19) . . . . ?
C7 C8 C12 N2 -0.31(17) . . . . ?
C7 C8 C12 C13 177.63(12) . . . . ?
C1 C6 C7 S1 39.29(16) . . . . ?
C1 C6 C7 C8 -141.18(15) . . . . ?
C1 C6 C5 C4 -2.8(2) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C5 C6 C7 S1 -134.44(12) . . . . ?
C5 C6 C7 C8 45.1(2) . . . . ?
C5 C6 C1 C2 1.9(2) . . . . ?
C18 C13 C12 N2 142.34(13) . . . . ?
C18 C13 C12 C8 -35.6(2) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C18 C17 C16 C15 -0.2(2) . . . . ?
C14 C13 C12 N2 -32.20(18) . . . . ?
C14 C13 C12 C8 149.91(14) . . . . ?
C14 C13 C18 C17 0.2(2) . . . . ?
C4 C3 C2 C1 -2.0(2) . . . . ?
C17 C16 C15 C14 0.2(2) . . . . ?
C10 O4 C9 O3 2.5(2) . . . . ?
C10 O4 C9 C8 -176.75(12) . . . . ?

_olex2_exptl_crystal_mounting_method .
_olex2_submission_original_sample_id 9y
_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 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.860
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bam22_s2527_fr233_autored
_database_code_depnum_ccdc_archive 'CCDC 2219743'
loop_
_audit_author_name
_audit_author_address
'Indrek pernik'
;The University of Sydney
Australia
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_audit_creation_date             2022-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 3-phenyl-5-(pyrrolidin-1-yl)isothiazole-4-carboxylate'
_chemical_formula_moiety         'C16 H18 N2 O2 S'
_chemical_formula_sum            'C16 H18 N2 O2 S'
_chemical_formula_weight         302.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H18 N2 O2 S'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0494(2)
_cell_length_b                   10.37004(19)
_cell_length_c                   26.5033(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.2575(19)
_cell_angle_gamma                90
_cell_volume                     2988.29(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    61003
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      45.2090
_cell_measurement_theta_min      1.8830
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_preparation       .
_exptl_crystal_recrystallization_method 'grown from n-hexane solution'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.617
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            187266
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.617
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.848
_diffrn_reflns_theta_min         1.897
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.617
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -350.17   9.83   1.50   40.00  -7.62 -25.77 -30.17    --   240
  2  ω      1.55  99.05   1.50   40.00    --   57.99-101.76-144.21   65
  3  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27  72.26   66
  4  ω     -5.24  50.26   1.50   40.00    --   26.32  80.15  11.44   37
  5  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27 -29.74   66
  6  ω   -106.28   1.72   1.50   40.00    --  -25.77 -73.76 178.75   72
  7  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27 123.26   66
  8  ω   -106.28   1.72   1.50   40.00    --  -25.77 -73.76  76.75   72
  9  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27 -83.74   66
 10  ω   -106.28   1.72   1.50   40.00    --  -25.77 -73.76 -79.25   72
 11  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27 174.26   66
 12  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27  21.26   66
 13  ω    -92.78  18.22   1.50   40.00    --  -10.77 -73.76  25.75   74
 14  ω    -56.95  42.05   1.50   40.00    --  -25.77  83.27-134.74   66
 15  ω    -92.78  18.22   1.50   40.00    --  -10.77 -73.76-154.25   74
 16  ω   -106.28   1.72   1.50   40.00    --  -25.77 -73.76  25.75   72
 17  φ   -333.16  26.84   1.50   40.00   4.41 -25.77 -76.41    --   240
 18  ω    -92.78  18.22   1.50   40.00    --  -10.77 -73.76 115.75   74
 19  ω   -106.28   1.72   1.50   40.00    --  -25.77 -73.76 127.75   72
 20  ω    -92.78  18.22   1.50   40.00    --  -10.77 -73.76 -64.25   74
 21  ω    -24.76  86.24   1.50   40.00    --    4.23  73.76 -25.75   74
 22  ω   -106.28   1.72   1.50   40.00    --  -25.77 -73.76-130.25   72
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0221087000
_diffrn_orient_matrix_UB_12      -0.0226085000
_diffrn_orient_matrix_UB_13      -0.0219416000
_diffrn_orient_matrix_UB_21      0.0417160000
_diffrn_orient_matrix_UB_22      -0.0414674000
_diffrn_orient_matrix_UB_23      0.0157407000
_diffrn_orient_matrix_UB_31      -0.0450058000
_diffrn_orient_matrix_UB_32      -0.0495046000
_diffrn_orient_matrix_UB_33      -0.0031849000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10679
_reflns_number_total             15899
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         15899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.0927
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+5.3860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1954
_refine_special_details          ?
_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:
 C13(H13A,H13B), C19(H19A,H19B), C20(H20A,H20B), C25(H25A,H25B), C27(H27A,
 H27B), C18(H18A,H18B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C35(H35), C36(H36), C38(H38), C40(H40), C26(H26), C28(H28),
 C30(H30), C32(H32), C34(H34)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.93957(4) 0.78023(5) 0.09817(2) 0.01959(11) Uani 1 1 d . . . . .
O3 O 0.51397(12) 0.76229(14) 0.06802(5) 0.0172(3) Uani 1 1 d . . . . .
O4 O 0.55042(12) 0.74767(13) 0.15405(5) 0.0159(3) Uani 1 1 d . . . . .
N5 N 0.76435(14) 0.62363(16) 0.04815(7) 0.0157(3) Uani 1 1 d . . . . .
C7 C 0.71945(16) 0.78136(18) 0.11382(7) 0.0144(3) Uani 1 1 d . . . . .
C10 C 0.58507(16) 0.76343(17) 0.10879(7) 0.0142(3) Uani 1 1 d . . . . .
C13 C 0.65940(17) 0.53454(19) 0.04560(8) 0.0171(3) Uani 1 1 d . . . . .
H13A H 0.585088 0.569604 0.023419 0.020 Uiso 1 1 calc R U . . .
H13B H 0.640682 0.517859 0.080182 0.020 Uiso 1 1 calc R U . . .
N16 N 0.90998(15) 0.88066(17) 0.14331(7) 0.0203(3) Uani 1 1 d . . . . .
C17 C 0.79101(16) 0.71940(18) 0.08256(7) 0.0150(3) Uani 1 1 d . . . . .
C19 C 0.86081(18) 0.56967(19) 0.02281(8) 0.0179(3) Uani 1 1 d . . . . .
H19A H 0.929716 0.534920 0.048204 0.022 Uiso 1 1 calc R U . . .
H19B H 0.892967 0.635466 0.001562 0.022 Uiso 1 1 calc R U . . .
C20 C 0.41890(18) 0.7327(2) 0.15310(8) 0.0209(4) Uani 1 1 d . . . . .
H20A H 0.405641 0.680178 0.182837 0.025 Uiso 1 1 calc R U . . .
H20B H 0.381229 0.686674 0.121453 0.025 Uiso 1 1 calc R U . . .
C21 C 0.79221(17) 0.86968(18) 0.14775(8) 0.0160(3) Uani 1 1 d . . . . .
C25 C 0.70383(18) 0.41178(19) 0.02253(8) 0.0178(3) Uani 1 1 d . . . . .
H25A H 0.745320 0.353169 0.049683 0.021 Uiso 1 1 calc R U . . .
H25B H 0.634543 0.365466 0.001288 0.021 Uiso 1 1 calc R U . . .
C27 C 0.79418(19) 0.46249(19) -0.01032(8) 0.0189(4) Uani 1 1 d . . . . .
H27A H 0.852080 0.394252 -0.016892 0.023 Uiso 1 1 calc R U . . .
H27B H 0.750333 0.496502 -0.043489 0.023 Uiso 1 1 calc R U . . .
C29 C 0.74758(18) 0.95233(19) 0.18615(8) 0.0181(3) Uani 1 1 d . . . . .
C33 C 0.80944(19) 0.9532(2) 0.23676(9) 0.0218(4) Uani 1 1 d . . . . .
H33 H 0.879994 0.900383 0.246483 0.026 Uiso 1 1 calc R U . . .
C35 C 0.64520(19) 1.0315(2) 0.17239(9) 0.0225(4) Uani 1 1 d . . . . .
H35 H 0.602794 1.032571 0.137908 0.027 Uiso 1 1 calc R U . . .
C36 C 0.6660(2) 1.1075(2) 0.25920(10) 0.0279(5) Uani 1 1 d . . . . .
H36 H 0.637474 1.159358 0.284202 0.033 Uiso 1 1 calc R U . . .
C37 C 0.3578(2) 0.8621(2) 0.15494(10) 0.0264(4) Uani 1 1 d . . . . .
H37A H 0.371126 0.914212 0.125567 0.040 Uiso 1 1 calc R U . . .
H37B H 0.393129 0.906448 0.186827 0.040 Uiso 1 1 calc R U . . .
H37C H 0.269315 0.849904 0.153623 0.040 Uiso 1 1 calc R U . . .
C38 C 0.6047(2) 1.1089(2) 0.20888(10) 0.0274(5) Uani 1 1 d . . . . .
H38 H 0.534925 1.162833 0.199266 0.033 Uiso 1 1 calc R U . . .
C40 C 0.7689(2) 1.0306(2) 0.27312(9) 0.0271(5) Uani 1 1 d . . . . .
H40 H 0.811685 1.030728 0.307541 0.032 Uiso 1 1 calc R U . . .
S2 S 0.44748(4) 0.26652(5) 0.08390(2) 0.01747(10) Uani 1 1 d . . . . .
O1 O 0.02247(12) 0.25630(15) 0.06569(5) 0.0181(3) Uani 1 1 d . . . . .
O2 O 0.07113(12) 0.25530(14) 0.15166(5) 0.0152(2) Uani 1 1 d . . . . .
C6 C 0.09935(16) 0.25927(17) 0.10466(7) 0.0133(3) Uani 1 1 d . . . . .
N8 N 0.42697(14) 0.36807(16) 0.13027(7) 0.0163(3) Uani 1 1 d . . . . .
N9 N 0.26562(14) 0.11107(15) 0.03929(6) 0.0150(3) Uani 1 1 d . . . . .
C11 C 0.31165(16) 0.35860(17) 0.13798(7) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.23304(15) 0.27096(17) 0.10613(7) 0.0132(3) Uani 1 1 d . . . . .
C14 C 0.29804(16) 0.20724(17) 0.07284(7) 0.0134(3) Uani 1 1 d . . . . .
C15 C 0.27693(16) 0.44264(18) 0.17831(7) 0.0142(3) Uani 1 1 d . . . . .
C18 C 0.15992(17) 0.02478(19) 0.03927(8) 0.0177(3) Uani 1 1 d . . . . .
H18A H 0.084474 0.060829 0.018230 0.021 Uiso 1 1 calc R U . . .
H18B H 0.145058 0.009935 0.074559 0.021 Uiso 1 1 calc R U . . .
C22 C 0.35729(18) 0.05392(18) 0.01220(8) 0.0167(3) Uani 1 1 d . . . . .
H22A H 0.427644 0.018256 0.036594 0.020 Uiso 1 1 calc R U . . .
H22B H 0.388112 0.118118 -0.010101 0.020 Uiso 1 1 calc R U . . .
C23 C 0.19891(18) -0.10002(19) 0.01573(8) 0.0190(4) Uani 1 1 d . . . . .
H23A H 0.242155 -0.158551 0.042528 0.023 Uiso 1 1 calc R U . . .
H23B H 0.127005 -0.145502 -0.004043 0.023 Uiso 1 1 calc R U . . .
C24 C -0.05874(17) 0.2582(2) 0.15458(8) 0.0223(4) Uani 1 1 d . . . . .
H24A H -0.099518 0.178195 0.139874 0.027 Uiso 1 1 calc R U . . .
H24B H -0.099135 0.332730 0.135172 0.027 Uiso 1 1 calc R U . . .
C26 C 0.17879(17) 0.52896(19) 0.16789(8) 0.0168(3) Uani 1 1 d . . . . .
H26 H 0.128624 0.531003 0.134830 0.020 Uiso 1 1 calc R U . . .
C28 C 0.34875(17) 0.43927(19) 0.22719(8) 0.0169(3) Uani 1 1 d . . . . .
H28 H 0.415343 0.380268 0.234471 0.020 Uiso 1 1 calc R U . . .
C30 C 0.32353(19) 0.52156(19) 0.26525(8) 0.0183(4) Uani 1 1 d . . . . .
H30 H 0.372271 0.518225 0.298587 0.022 Uiso 1 1 calc R U . . .
C31 C 0.2852(2) -0.0525(2) -0.01936(8) 0.0201(4) Uani 1 1 d . . . . .
H31A H 0.340391 -0.122271 -0.026977 0.024 Uiso 1 1 calc R U . . .
H31B H 0.238495 -0.018340 -0.051975 0.024 Uiso 1 1 calc R U . . .
C32 C 0.15464(19) 0.6122(2) 0.20621(8) 0.0202(4) Uani 1 1 d . . . . .
H32 H 0.088294 0.671577 0.199171 0.024 Uiso 1 1 calc R U . . .
C34 C 0.2274(2) 0.6085(2) 0.25466(8) 0.0211(4) Uani 1 1 d . . . . .
H34 H 0.211129 0.665812 0.280606 0.025 Uiso 1 1 calc R U . . .
C39 C -0.0678(2) 0.2694(2) 0.20991(9) 0.0272(4) Uani 1 1 d . . . . .
H39A H -0.154492 0.274123 0.213368 0.041 Uiso 1 1 calc R U . . .
H39B H -0.025096 0.347601 0.224230 0.041 Uiso 1 1 calc R U . . .
H39C H -0.029626 0.193800 0.228489 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N16 1.6620(19) . ?
S1 C17 1.7383(18) . ?
O3 C10 1.218(2) . ?
O4 C10 1.333(2) . ?
O4 C20 1.457(2) . ?
N5 C13 1.475(2) . ?
N5 C17 1.345(2) . ?
N5 C19 1.468(2) . ?
C7 C10 1.479(2) . ?
C7 C17 1.399(3) . ?
C7 C21 1.427(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C25 1.531(3) . ?
N16 C21 1.332(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C27 1.522(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C37 1.507(3) . ?
C21 C29 1.480(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C27 1.530(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C29 C33 1.393(3) . ?
C29 C35 1.393(3) . ?
C33 H33 0.9500 . ?
C33 C40 1.388(3) . ?
C35 H35 0.9500 . ?
C35 C38 1.391(3) . ?
C36 H36 0.9500 . ?
C36 C38 1.384(4) . ?
C36 C40 1.383(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38 0.9500 . ?
C40 H40 0.9500 . ?
S2 N8 1.6643(17) . ?
S2 C14 1.7372(18) . ?
O1 C6 1.215(2) . ?
O2 C6 1.337(2) . ?
O2 C24 1.451(2) . ?
C6 C12 1.476(2) . ?
N8 C11 1.329(2) . ?
N9 C14 1.342(2) . ?
N9 C18 1.471(2) . ?
N9 C22 1.467(2) . ?
C11 C12 1.425(2) . ?
C11 C15 1.482(3) . ?
C12 C14 1.399(2) . ?
C15 C26 1.395(3) . ?
C15 C28 1.394(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C23 1.532(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C31 1.521(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C31 1.528(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C39 1.492(3) . ?
C26 H26 0.9500 . ?
C26 C32 1.395(3) . ?
C28 H28 0.9500 . ?
C28 C30 1.387(3) . ?
C30 H30 0.9500 . ?
C30 C34 1.383(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32 0.9500 . ?
C32 C34 1.389(3) . ?
C34 H34 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

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
N16 S1 C17 95.75(9) . . ?
C10 O4 C20 116.31(15) . . ?
C17 N5 C13 124.68(16) . . ?
C17 N5 C19 120.16(16) . . ?
C19 N5 C13 111.68(15) . . ?
C17 C7 C10 123.58(17) . . ?
C17 C7 C21 110.71(16) . . ?
C21 C7 C10 125.55(17) . . ?
O3 C10 O4 123.66(16) . . ?
O3 C10 C7 124.06(17) . . ?
O4 C10 C7 112.28(16) . . ?
N5 C13 H13A 111.1 . . ?
N5 C13 H13B 111.1 . . ?
N5 C13 C25 103.52(15) . . ?
H13A C13 H13B 109.0 . . ?
C25 C13 H13A 111.1 . . ?
C25 C13 H13B 111.1 . . ?
C21 N16 S1 109.30(14) . . ?
N5 C17 S1 120.85(14) . . ?
N5 C17 C7 131.45(17) . . ?
C7 C17 S1 107.56(13) . . ?
N5 C19 H19A 111.1 . . ?
N5 C19 H19B 111.1 . . ?
N5 C19 C27 103.07(15) . . ?
H19A C19 H19B 109.1 . . ?
C27 C19 H19A 111.1 . . ?
C27 C19 H19B 111.1 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 C37 110.83(17) . . ?
H20A C20 H20B 108.1 . . ?
C37 C20 H20A 109.5 . . ?
C37 C20 H20B 109.5 . . ?
C7 C21 C29 125.84(16) . . ?
N16 C21 C7 116.66(18) . . ?
N16 C21 C29 117.47(17) . . ?
C13 C25 H25A 111.1 . . ?
C13 C25 H25B 111.1 . . ?
H25A C25 H25B 109.1 . . ?
C27 C25 C13 103.28(15) . . ?
C27 C25 H25A 111.1 . . ?
C27 C25 H25B 111.1 . . ?
C19 C27 C25 102.73(16) . . ?
C19 C27 H27A 111.2 . . ?
C19 C27 H27B 111.2 . . ?
C25 C27 H27A 111.2 . . ?
C25 C27 H27B 111.2 . . ?
H27A C27 H27B 109.1 . . ?
C33 C29 C21 119.95(18) . . ?
C35 C29 C21 121.04(19) . . ?
C35 C29 C33 118.99(19) . . ?
C29 C33 H33 119.7 . . ?
C40 C33 C29 120.6(2) . . ?
C40 C33 H33 119.7 . . ?
C29 C35 H35 119.8 . . ?
C38 C35 C29 120.3(2) . . ?
C38 C35 H35 119.8 . . ?
C38 C36 H36 120.0 . . ?
C40 C36 H36 120.0 . . ?
C40 C36 C38 120.1(2) . . ?
C20 C37 H37A 109.5 . . ?
C20 C37 H37B 109.5 . . ?
C20 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38 120.0 . . ?
C36 C38 C35 120.1(2) . . ?
C36 C38 H38 120.0 . . ?
C33 C40 H40 120.0 . . ?
C36 C40 C33 120.0(2) . . ?
C36 C40 H40 120.0 . . ?
N8 S2 C14 95.64(8) . . ?
C6 O2 C24 116.47(15) . . ?
O1 C6 O2 123.18(16) . . ?
O1 C6 C12 124.70(17) . . ?
O2 C6 C12 112.10(15) . . ?
C11 N8 S2 109.08(13) . . ?
C14 N9 C18 124.79(16) . . ?
C14 N9 C22 119.91(15) . . ?
C22 N9 C18 111.80(15) . . ?
N8 C11 C12 117.12(16) . . ?
N8 C11 C15 116.47(16) . . ?
C12 C11 C15 126.40(16) . . ?
C11 C12 C6 124.72(16) . . ?
C14 C12 C6 124.65(16) . . ?
C14 C12 C11 110.34(15) . . ?
N9 C14 S2 120.56(13) . . ?
N9 C14 C12 131.51(16) . . ?
C12 C14 S2 107.80(13) . . ?
C26 C15 C11 121.78(17) . . ?
C28 C15 C11 118.55(17) . . ?
C28 C15 C26 119.58(17) . . ?
N9 C18 H18A 111.1 . . ?
N9 C18 H18B 111.1 . . ?
N9 C18 C23 103.49(15) . . ?
H18A C18 H18B 109.0 . . ?
C23 C18 H18A 111.1 . . ?
C23 C18 H18B 111.1 . . ?
N9 C22 H22A 111.2 . . ?
N9 C22 H22B 111.2 . . ?
N9 C22 C31 102.87(15) . . ?
H22A C22 H22B 109.1 . . ?
C31 C22 H22A 111.2 . . ?
C31 C22 H22B 111.2 . . ?
C18 C23 H23A 111.1 . . ?
C18 C23 H23B 111.1 . . ?
H23A C23 H23B 109.1 . . ?
C31 C23 C18 103.09(16) . . ?
C31 C23 H23A 111.1 . . ?
C31 C23 H23B 111.1 . . ?
O2 C24 H24A 110.3 . . ?
O2 C24 H24B 110.3 . . ?
O2 C24 C39 107.09(17) . . ?
H24A C24 H24B 108.6 . . ?
C39 C24 H24A 110.3 . . ?
C39 C24 H24B 110.3 . . ?
C15 C26 H26 120.1 . . ?
C32 C26 C15 119.73(18) . . ?
C32 C26 H26 120.1 . . ?
C15 C28 H28 119.8 . . ?
C30 C28 C15 120.38(18) . . ?
C30 C28 H28 119.8 . . ?
C28 C30 H30 120.0 . . ?
C34 C30 C28 120.00(19) . . ?
C34 C30 H30 120.0 . . ?
C22 C31 C23 102.82(16) . . ?
C22 C31 H31A 111.2 . . ?
C22 C31 H31B 111.2 . . ?
C23 C31 H31A 111.2 . . ?
C23 C31 H31B 111.2 . . ?
H31A C31 H31B 109.1 . . ?
C26 C32 H32 119.9 . . ?
C34 C32 C26 120.12(19) . . ?
C34 C32 H32 119.9 . . ?
C30 C34 C32 120.19(19) . . ?
C30 C34 H34 119.9 . . ?
C32 C34 H34 119.9 . . ?
C24 C39 H39A 109.5 . . ?
C24 C39 H39B 109.5 . . ?
C24 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N16 C21 C7 -1.5(2) . . . . ?
S1 N16 C21 C29 -179.76(15) . . . . ?
N5 C13 C25 C27 -28.6(2) . . . . ?
N5 C19 C27 C25 -34.87(19) . . . . ?
C7 C21 C29 C33 129.2(2) . . . . ?
C7 C21 C29 C35 -51.9(3) . . . . ?
C10 O4 C20 C37 -87.6(2) . . . . ?
C10 C7 C17 S1 174.57(15) . . . . ?
C10 C7 C17 N5 -9.8(3) . . . . ?
C10 C7 C21 N16 -173.82(18) . . . . ?
C10 C7 C21 C29 4.3(3) . . . . ?
C13 N5 C17 S1 156.60(15) . . . . ?
C13 N5 C17 C7 -18.5(3) . . . . ?
C13 N5 C19 C27 17.6(2) . . . . ?
C13 C25 C27 C19 39.59(19) . . . . ?
N16 S1 C17 N5 -175.89(16) . . . . ?
N16 S1 C17 C7 0.26(15) . . . . ?
N16 C21 C29 C33 -52.7(3) . . . . ?
N16 C21 C29 C35 126.2(2) . . . . ?
C17 S1 N16 C21 0.67(16) . . . . ?
C17 N5 C13 C25 -151.84(18) . . . . ?
C17 N5 C19 C27 177.53(17) . . . . ?
C17 C7 C10 O3 -44.0(3) . . . . ?
C17 C7 C10 O4 135.53(19) . . . . ?
C17 C7 C21 N16 1.7(3) . . . . ?
C17 C7 C21 C29 179.83(18) . . . . ?
C19 N5 C13 C25 7.0(2) . . . . ?
C19 N5 C17 S1 -0.6(3) . . . . ?
C19 N5 C17 C7 -175.66(19) . . . . ?
C20 O4 C10 O3 -2.0(3) . . . . ?
C20 O4 C10 C7 178.42(16) . . . . ?
C21 C7 C10 O3 131.0(2) . . . . ?
C21 C7 C10 O4 -49.5(3) . . . . ?
C21 C7 C17 S1 -1.1(2) . . . . ?
C21 C7 C17 N5 174.5(2) . . . . ?
C21 C29 C33 C40 179.8(2) . . . . ?
C21 C29 C35 C38 -179.8(2) . . . . ?
C29 C33 C40 C36 0.1(3) . . . . ?
C29 C35 C38 C36 -0.1(4) . . . . ?
C33 C29 C35 C38 -0.8(3) . . . . ?
C35 C29 C33 C40 0.8(3) . . . . ?
C38 C36 C40 C33 -1.0(4) . . . . ?
C40 C36 C38 C35 1.0(4) . . . . ?
S2 N8 C11 C12 -1.3(2) . . . . ?
S2 N8 C11 C15 179.90(14) . . . . ?
O1 C6 C12 C11 132.3(2) . . . . ?
O1 C6 C12 C14 -40.8(3) . . . . ?
O2 C6 C12 C11 -46.1(2) . . . . ?
O2 C6 C12 C14 140.72(18) . . . . ?
C6 O2 C24 C39 -173.12(17) . . . . ?
C6 C12 C14 S2 172.50(15) . . . . ?
C6 C12 C14 N9 -11.8(3) . . . . ?
N8 S2 C14 N9 -175.58(16) . . . . ?
N8 S2 C14 C12 0.72(15) . . . . ?
N8 C11 C12 C6 -172.08(18) . . . . ?
N8 C11 C12 C14 1.9(2) . . . . ?
N8 C11 C15 C26 123.5(2) . . . . ?
N8 C11 C15 C28 -53.2(2) . . . . ?
N9 C18 C23 C31 -28.7(2) . . . . ?
N9 C22 C31 C23 -35.14(19) . . . . ?
C11 C12 C14 S2 -1.48(19) . . . . ?
C11 C12 C14 N9 174.26(19) . . . . ?
C11 C15 C26 C32 -175.71(18) . . . . ?
C11 C15 C28 C30 176.39(17) . . . . ?
C12 C11 C15 C26 -55.2(3) . . . . ?
C12 C11 C15 C28 128.2(2) . . . . ?
C14 S2 N8 C11 0.31(15) . . . . ?
C14 N9 C18 C23 -151.80(18) . . . . ?
C14 N9 C22 C31 177.68(17) . . . . ?
C15 C11 C12 C6 6.6(3) . . . . ?
C15 C11 C12 C14 -179.46(18) . . . . ?
C15 C26 C32 C34 -0.5(3) . . . . ?
C15 C28 C30 C34 -0.6(3) . . . . ?
C18 N9 C14 S2 158.03(15) . . . . ?
C18 N9 C14 C12 -17.3(3) . . . . ?
C18 N9 C22 C31 17.8(2) . . . . ?
C18 C23 C31 C22 39.82(19) . . . . ?
C22 N9 C14 S2 0.9(2) . . . . ?
C22 N9 C14 C12 -174.39(19) . . . . ?
C22 N9 C18 C23 6.9(2) . . . . ?
C24 O2 C6 O1 -5.1(3) . . . . ?
C24 O2 C6 C12 173.44(16) . . . . ?
C26 C15 C28 C30 -0.4(3) . . . . ?
C26 C32 C34 C30 -0.5(3) . . . . ?
C28 C15 C26 C32 0.9(3) . . . . ?
C28 C30 C34 C32 1.1(3) . . . . ?

_olex2_submission_original_sample_id BAM_9a
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.854
_oxdiff_exptl_absorpt_empirical_full_min 0.412
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bam22_s2580_sn950
_database_code_depnum_ccdc_archive 'CCDC 2219744'
loop_
_audit_author_name
_audit_author_address
'Indrek pernik'
;The University of Sydney
Australia
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2023-03-31 downloaded from the CCDC.
;
_audit_creation_date             2022-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_chemical_name_systematic        
'ethyl 2-(cyclopentanecarbonothioyl)-3-phenylbutanoate'
_chemical_formula_moiety         'C17 H21 N O2 S'
_chemical_formula_sum            'C17 H21 N O2 S'
_chemical_formula_weight         303.428
_chemical_oxdiff_formula         C17H18N1S1O3
_chemical_oxdiff_usercomment     10b
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
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

_symmetry_Int_Tables_number      14
_cell_length_a                   9.7409(1)
_cell_length_b                   7.7066(1)
_cell_length_c                   21.1913(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.380(1)
_cell_angle_gamma                90
_cell_volume                     1590.35(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14017
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.4090
_cell_measurement_theta_min      4.1570
_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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             651.148
_exptl_crystal_preparation       .
_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
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_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)'
_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_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.0802
_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
_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)
;
_atom_sites_solution_primary     dual
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_
_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) . ?

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) . . ?


_olex2_exptl_crystal_mounting_method .
_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
