# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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. 
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data_cu_220519_lht_2_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2cmj2m
_database_code_depnum_ccdc_archive 'CCDC 2193500'
loop_
_audit_author_name
_audit_author_address
'Haitao Liu'
;Shandong Normal University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H25 N O S'
_chemical_formula_sum            'C16 H25 N O S'
_chemical_formula_weight         279.43
_chemical_melting_point          ?
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/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                   9.3185(8)
_cell_length_b                   8.0794(7)
_cell_length_c                   20.8639(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.434(4)
_cell_angle_gamma                90
_cell_volume                     1570.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7555
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      4.24
_shelx_estimated_absorpt_T_max   0.621
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0766 after correction.
The Ratio of minimum to maximum transmission is 0.6455.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9264
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.325
_diffrn_reflns_theta_min         4.238
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2631
_reflns_number_total             2832
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.059
_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)+(0.0547P)²+0.8058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1189
_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:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,
 H16B,H16C)
;
_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 0.61000(4) 0.70371(5) 0.30555(2) 0.02622(16) Uani 1 1 d . . . . .
O1 O 0.55336(14) 0.61760(17) 0.24754(6) 0.0325(3) Uani 1 1 d . . . . .
N1 N 0.65528(15) 0.57427(18) 0.36539(7) 0.0260(3) Uani 1 1 d . . . . .
C1 C 0.5743(2) 0.4132(2) 0.37282(8) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.6151(2) 0.3391(3) 0.43821(9) 0.0354(4) Uani 1 1 d . . . . .
H2A H 0.575350 0.409994 0.472463 0.043 Uiso 1 1 calc R . . . .
H2B H 0.570487 0.228319 0.442088 0.043 Uiso 1 1 calc R . . . .
C3 C 0.7756(2) 0.3228(3) 0.44826(10) 0.0432(5) Uani 1 1 d . . . . .
H3A H 0.795912 0.275429 0.491139 0.052 Uiso 1 1 calc R . . . .
H3B H 0.816258 0.247756 0.415566 0.052 Uiso 1 1 calc R . . . .
C4 C 0.8432(2) 0.4925(3) 0.44280(9) 0.0410(5) Uani 1 1 d . . . . .
H4A H 0.948187 0.481299 0.448871 0.049 Uiso 1 1 calc R . . . .
H4B H 0.806770 0.562813 0.477985 0.049 Uiso 1 1 calc R . . . .
C5 C 0.81466(19) 0.5810(2) 0.37898(9) 0.0310(4) Uani 1 1 d . . . . .
C6 C 0.6056(2) 0.2863(2) 0.31943(10) 0.0370(5) Uani 1 1 d . . . . .
H6A H 0.586298 0.336773 0.277527 0.056 Uiso 1 1 calc GR . . . .
H6B H 0.543849 0.189236 0.324921 0.056 Uiso 1 1 calc GR . . . .
H6C H 0.706433 0.252398 0.321945 0.056 Uiso 1 1 calc GR . . . .
C7 C 0.4130(2) 0.4460(2) 0.37330(9) 0.0337(4) Uani 1 1 d . . . . .
H7A H 0.390967 0.527686 0.406542 0.051 Uiso 1 1 calc GR . . . .
H7B H 0.361905 0.342699 0.382289 0.051 Uiso 1 1 calc GR . . . .
H7C H 0.382611 0.488795 0.331396 0.051 Uiso 1 1 calc GR . . . .
C8 C 0.9065(2) 0.5050(3) 0.32548(9) 0.0365(4) Uani 1 1 d . . . . .
H8A H 0.893908 0.384601 0.325202 0.055 Uiso 1 1 calc GR . . . .
H8B H 1.007738 0.531616 0.333187 0.055 Uiso 1 1 calc GR . . . .
H8C H 0.876178 0.550485 0.283981 0.055 Uiso 1 1 calc GR . . . .
C9 C 0.8623(2) 0.7620(3) 0.38812(11) 0.0416(5) Uani 1 1 d . . . . .
H9A H 0.859142 0.819319 0.346745 0.062 Uiso 1 1 calc GR . . . .
H9B H 0.960410 0.764616 0.405303 0.062 Uiso 1 1 calc GR . . . .
H9C H 0.797559 0.817179 0.418134 0.062 Uiso 1 1 calc GR . . . .
C10 C 0.45745(19) 0.8081(2) 0.33951(8) 0.0274(4) Uani 1 1 d . . . . .
C11 C 0.3430(2) 0.8472(3) 0.29928(9) 0.0337(4) Uani 1 1 d . . . . .
H11 H 0.340978 0.808475 0.256297 0.040 Uiso 1 1 calc R . . . .
C12 C 0.2311(2) 0.9439(3) 0.32262(10) 0.0372(4) Uani 1 1 d . . . . .
H12 H 0.152538 0.970523 0.295226 0.045 Uiso 1 1 calc R . . . .
C13 C 0.2326(2) 1.0017(2) 0.38506(10) 0.0331(4) Uani 1 1 d . . . . .
C14 C 0.3486(2) 0.9615(2) 0.42439(9) 0.0330(4) Uani 1 1 d . . . . .
H14 H 0.350907 1.000389 0.467350 0.040 Uiso 1 1 calc R . . . .
C15 C 0.4609(2) 0.8655(2) 0.40192(9) 0.0312(4) Uani 1 1 d . . . . .
H15 H 0.539696 0.839417 0.429244 0.037 Uiso 1 1 calc R . . . .
C16 C 0.1108(2) 1.1070(3) 0.40960(11) 0.0437(5) Uani 1 1 d . . . . .
H16A H 0.069156 1.054623 0.447518 0.066 Uiso 1 1 calc GR . . . .
H16B H 0.037027 1.117794 0.376142 0.066 Uiso 1 1 calc GR . . . .
H16C H 0.147282 1.216958 0.421058 0.066 Uiso 1 1 calc GR . . . .


_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 O1 1.4892(13) . ?
S1 N1 1.6800(14) . ?
S1 C10 1.8027(18) . ?
N1 C1 1.513(2) . ?
N1 C5 1.511(2) . ?
C1 C2 1.535(2) . ?
C1 C6 1.543(3) . ?
C1 C7 1.527(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.515(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.514(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.533(3) . ?
C5 C8 1.539(3) . ?
C5 C9 1.539(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.389(3) . ?
C10 C15 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 C14 1.390(3) . ?
C13 C16 1.511(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 S1 N1 113.49(8) . . ?
O1 S1 C10 105.21(8) . . ?
N1 S1 C10 101.16(8) . . ?
C1 N1 S1 119.28(12) . . ?
C5 N1 S1 110.98(11) . . ?
C5 N1 C1 120.14(14) . . ?
N1 C1 C2 107.87(15) . . ?
N1 C1 C6 113.61(14) . . ?
N1 C1 C7 110.07(15) . . ?
C2 C1 C6 109.60(16) . . ?
C7 C1 C2 107.38(15) . . ?
C7 C1 C6 108.14(16) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.22(16) . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 C2 108.77(17) . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C3 C4 C5 114.73(17) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
N1 C5 C4 108.05(15) . . ?
N1 C5 C8 113.60(15) . . ?
N1 C5 C9 109.85(15) . . ?
C4 C5 C8 110.51(16) . . ?
C4 C5 C9 106.71(16) . . ?
C8 C5 C9 107.91(16) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 118.25(14) . . ?
C15 C10 S1 120.96(14) . . ?
C15 C10 C11 120.34(17) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.32(17) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.06(18) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 118.60(17) . . ?
C12 C13 C16 120.47(19) . . ?
C14 C13 C16 120.94(18) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.09(17) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 119.58(17) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 N1 C1 C2 -168.12(12) . . . . ?
S1 N1 C1 C6 70.18(19) . . . . ?
S1 N1 C1 C7 -51.26(17) . . . . ?
S1 N1 C5 C4 167.26(13) . . . . ?
S1 N1 C5 C8 -69.75(18) . . . . ?
S1 N1 C5 C9 51.21(17) . . . . ?
S1 C10 C11 C12 -172.91(15) . . . . ?
S1 C10 C15 C14 172.76(14) . . . . ?
O1 S1 N1 C1 -30.75(14) . . . . ?
O1 S1 N1 C5 115.50(12) . . . . ?
O1 S1 C10 C11 -24.26(17) . . . . ?
O1 S1 C10 C15 163.36(15) . . . . ?
N1 S1 C10 C11 -142.60(15) . . . . ?
N1 S1 C10 C15 45.02(16) . . . . ?
N1 C1 C2 C3 -53.1(2) . . . . ?
C1 N1 C5 C4 -46.8(2) . . . . ?
C1 N1 C5 C8 76.2(2) . . . . ?
C1 N1 C5 C9 -162.88(15) . . . . ?
C1 C2 C3 C4 59.1(2) . . . . ?
C2 C3 C4 C5 -57.7(2) . . . . ?
C3 C4 C5 N1 49.8(2) . . . . ?
C3 C4 C5 C8 -75.0(2) . . . . ?
C3 C4 C5 C9 167.89(17) . . . . ?
C5 N1 C1 C2 48.75(19) . . . . ?
C5 N1 C1 C6 -73.0(2) . . . . ?
C5 N1 C1 C7 165.61(14) . . . . ?
C6 C1 C2 C3 71.0(2) . . . . ?
C7 C1 C2 C3 -171.74(17) . . . . ?
C10 S1 N1 C1 81.42(13) . . . . ?
C10 S1 N1 C5 -132.34(12) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C11 C12 C13 C16 179.72(19) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C16 C13 C14 C15 -179.66(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_561
_audit_block_doi                 10.5517/ccdc.csd.cc2cmj4p
_database_code_depnum_ccdc_archive 'CCDC 2193502'
loop_
_audit_author_name
_audit_author_address
'Haitao Liu'
;Shandong Normal University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_audit_creation_date             2021-09-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H19 N O S'
_chemical_formula_sum            'C23 H19 N O S'
_chemical_formula_weight         357.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.8102(4)
_cell_length_b                   17.8902(7)
_cell_length_c                   9.7282(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.643(4)
_cell_angle_gamma                90.00
_cell_volume                     1868.77(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3547
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4880
_cell_measurement_theta_min      3.7510
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12825
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         3.51
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.8636
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  58.00   1.00    5.18    --   19.03  65.00 -78.00   62
  2  ω    -47.00  42.00   1.00    5.18    --   19.03 -65.00 145.00   89
  3  ω    -41.00  11.00   1.00    5.18    --  -18.88 -77.00  30.00   52
  4  ω    -23.00   9.00   1.00    5.18    --  -18.88 -77.00  90.00   32
  5  ω    -39.00  11.00   1.00    5.18    --  -18.88 -77.00-120.00   50
  6  ω     -2.00  67.00   1.00    5.18    --   19.03  57.00   0.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0353070000
_diffrn_orient_matrix_UB_12      0.0248459000
_diffrn_orient_matrix_UB_13      0.0459184000
_diffrn_orient_matrix_UB_21      0.0256750000
_diffrn_orient_matrix_UB_22      0.0163807000
_diffrn_orient_matrix_UB_23      -0.0567252000
_diffrn_orient_matrix_UB_31      -0.0496036000
_diffrn_orient_matrix_UB_32      0.0261661000
_diffrn_orient_matrix_UB_33      -0.0080770000
_diffrn_oxdiff_digest_frames     
;
016d4d898dc8bcc9672f4849369f06cf4200027e104
;
_diffrn_oxdiff_digest_hkl        
;
0166507363254c9ea37014851ec93ea6299eaf
;
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3159
_reflns_number_total             4362
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.5753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21289(15) 0.53022(9) 0.11138(18) 0.0368(4) Uani 1 1 d . . .
C2 C 0.19399(16) 0.45975(10) 0.04777(19) 0.0435(4) Uani 1 1 d . . .
H2 H 0.1150 0.4463 0.0072 0.052 Uiso 1 1 calc R . .
C3 C 0.29044(17) 0.41130(10) 0.0453(2) 0.0463(4) Uani 1 1 d . . .
H3 H 0.2771 0.3652 0.0018 0.056 Uiso 1 1 calc R . .
C4 C 0.41075(16) 0.43020(10) 0.10804(19) 0.0422(4) Uani 1 1 d . . .
C5 C 0.43236(15) 0.49750(10) 0.17272(18) 0.0397(4) Uani 1 1 d . . .
H5 H 0.5115 0.5091 0.2154 0.048 Uiso 1 1 calc R . .
C6 C 0.33344(14) 0.54968(9) 0.17452(17) 0.0354(4) Uani 1 1 d . . .
C7 C 0.34999(15) 0.62285(10) 0.23141(17) 0.0369(4) Uani 1 1 d . . .
C8 C 0.25051(15) 0.67069(10) 0.21824(18) 0.0402(4) Uani 1 1 d . . .
H8 H 0.2599 0.7195 0.2506 0.048 Uiso 1 1 calc R . .
C9 C 0.13330(15) 0.64562(10) 0.15527(18) 0.0388(4) Uani 1 1 d . . .
C10 C 0.47248(15) 0.64668(10) 0.30689(19) 0.0393(4) Uani 1 1 d . . .
C11 C 0.5093(2) 0.62053(13) 0.4388(2) 0.0615(6) Uani 1 1 d . . .
H11 H 0.4583 0.5875 0.4801 0.074 Uiso 1 1 calc R . .
C12 C 0.6215(2) 0.64305(14) 0.5104(2) 0.0689(6) Uani 1 1 d . . .
H12 H 0.6449 0.6256 0.5997 0.083 Uiso 1 1 calc R . .
C13 C 0.69767(19) 0.69071(12) 0.4499(3) 0.0636(6) Uani 1 1 d . . .
H13 H 0.7729 0.7059 0.4979 0.076 Uiso 1 1 calc R . .
C14 C 0.6631(2) 0.71589(13) 0.3192(3) 0.0674(6) Uani 1 1 d . . .
H14 H 0.7158 0.7477 0.2776 0.081 Uiso 1 1 calc R . .
C15 C 0.54996(18) 0.69464(12) 0.2470(2) 0.0553(5) Uani 1 1 d . . .
H15 H 0.5267 0.7129 0.1582 0.066 Uiso 1 1 calc R . .
C16 C 0.62096(18) 0.38941(12) 0.1612(2) 0.0597(6) Uani 1 1 d . . .
H16A H 0.6521 0.4354 0.1278 0.090 Uiso 1 1 calc R . .
H16B H 0.6743 0.3490 0.1407 0.090 Uiso 1 1 calc R . .
H16C H 0.6191 0.3926 0.2594 0.090 Uiso 1 1 calc R . .
C17 C 0.04921(16) 0.79381(10) 0.1478(2) 0.0425(4) Uani 1 1 d . . .
C18 C 0.11231(18) 0.82045(12) 0.0414(2) 0.0527(5) Uani 1 1 d . . .
H18 H 0.1322 0.7881 -0.0276 0.063 Uiso 1 1 calc R . .
C19 C 0.1454(2) 0.89452(12) 0.0380(2) 0.0562(5) Uani 1 1 d . . .
H19 H 0.1887 0.9114 -0.0332 0.067 Uiso 1 1 calc R . .
C20 C 0.11626(17) 0.94476(11) 0.1375(2) 0.0510(5) Uani 1 1 d . . .
C21 C 0.05251(19) 0.91757(12) 0.2422(2) 0.0545(5) Uani 1 1 d . . .
H21 H 0.0312 0.9502 0.3100 0.065 Uiso 1 1 calc R . .
C22 C 0.01976(18) 0.84315(11) 0.2485(2) 0.0504(5) Uani 1 1 d . . .
H22 H -0.0222 0.8262 0.3207 0.061 Uiso 1 1 calc R . .
C23 C 0.1541(2) 1.02553(13) 0.1331(3) 0.0749(7) Uani 1 1 d . . .
H23A H 0.2352 1.0318 0.1834 0.112 Uiso 1 1 calc R . .
H23B H 0.0950 1.0558 0.1745 0.112 Uiso 1 1 calc R . .
H23C H 0.1562 1.0406 0.0387 0.112 Uiso 1 1 calc R . .
N1 N 0.11354(12) 0.57831(8) 0.10464(15) 0.0399(3) Uani 1 1 d . . .
O1 O 0.49856(12) 0.37636(7) 0.09531(16) 0.0557(4) Uani 1 1 d . . .
S1 S -0.00445(4) 0.70030(3) 0.14934(6) 0.05206(17) Uani 1 1 d . . .


_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
C1 C2 1.409(2) . ?
C1 C6 1.418(2) . ?
C1 N1 1.372(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(2) . ?
C4 C5 1.366(2) . ?
C4 O1 1.368(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.421(2) . ?
C6 C7 1.425(2) . ?
C7 C8 1.369(2) . ?
C7 C10 1.500(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.415(2) . ?
C9 N1 1.309(2) . ?
C9 S1 1.7771(17) . ?
C10 C11 1.381(3) . ?
C10 C15 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 O1 1.421(2) . ?
C17 C18 1.388(3) . ?
C17 C22 1.383(3) . ?
C17 S1 1.7713(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C20 C21 1.382(3) . ?
C20 C23 1.504(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C2 C1 C6 119.29(15) . . ?
N1 C1 C2 117.86(15) . . ?
N1 C1 C6 122.81(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.42(16) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.66(16) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.66(16) . . ?
C5 C4 O1 125.37(16) . . ?
O1 C4 C3 113.97(16) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.72(15) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.24(15) . . ?
C1 C6 C7 117.49(15) . . ?
C5 C6 C7 123.20(15) . . ?
C6 C7 C10 121.03(15) . . ?
C8 C7 C6 118.44(15) . . ?
C8 C7 C10 120.52(15) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.80(16) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 S1 123.01(13) . . ?
N1 C9 C8 123.59(15) . . ?
N1 C9 S1 113.23(12) . . ?
C11 C10 C7 120.13(17) . . ?
C15 C10 C7 121.09(17) . . ?
C15 C10 C11 118.78(17) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 120.0(2) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
C18 C17 S1 121.35(15) . . ?
C22 C17 C18 118.83(18) . . ?
C22 C17 S1 119.63(15) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.06(19) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 121.9(2) . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C23 121.3(2) . . ?
C21 C20 C19 117.39(19) . . ?
C21 C20 C23 121.3(2) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.62(19) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.18(19) . . ?
C21 C22 H22 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 N1 C1 117.79(14) . . ?
C4 O1 C16 117.59(15) . . ?
C17 S1 C9 104.25(8) . . ?

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
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C6 C7 C8 -2.0(2) . . . . ?
C1 C6 C7 C10 176.62(15) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C6 C7 176.86(16) . . . . ?
C2 C1 N1 C9 -175.33(16) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 O1 -179.05(17) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C3 C4 O1 C16 -177.11(17) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -175.62(17) . . . . ?
C5 C4 O1 C16 3.7(3) . . . . ?
C5 C6 C7 C8 175.00(16) . . . . ?
C5 C6 C7 C10 -6.4(3) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C1 N1 C9 2.2(3) . . . . ?
C6 C7 C8 C9 3.1(3) . . . . ?
C6 C7 C10 C11 -74.4(2) . . . . ?
C6 C7 C10 C15 105.6(2) . . . . ?
C7 C8 C9 N1 -1.5(3) . . . . ?
C7 C8 C9 S1 173.39(14) . . . . ?
C7 C10 C11 C12 -179.0(2) . . . . ?
C7 C10 C15 C14 180.00(19) . . . . ?
C8 C7 C10 C11 104.2(2) . . . . ?
C8 C7 C10 C15 -75.7(2) . . . . ?
C8 C9 N1 C1 -1.1(3) . . . . ?
C8 C9 S1 C17 29.50(18) . . . . ?
C10 C7 C8 C9 -175.58(16) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C10 -1.1(4) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C18 C17 S1 C9 61.34(17) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C18 C19 C20 C23 179.5(2) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C17 -0.8(3) . . . . ?
C22 C17 C18 C19 0.6(3) . . . . ?
C22 C17 S1 C9 -123.70(15) . . . . ?
C23 C20 C21 C22 -178.62(19) . . . . ?
N1 C1 C2 C3 176.76(17) . . . . ?
N1 C1 C6 C5 -177.77(15) . . . . ?
N1 C1 C6 C7 -0.6(2) . . . . ?
N1 C9 S1 C17 -155.09(14) . . . . ?
O1 C4 C5 C6 177.83(17) . . . . ?
S1 C9 N1 C1 -176.50(12) . . . . ?
S1 C17 C18 C19 175.59(15) . . . . ?
S1 C17 C22 C21 -174.85(15) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.635

####################################################################### 
# 
# 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_r20220422a
_audit_block_doi                 10.5517/ccdc.csd.cc2cmj5q
_database_code_depnum_ccdc_archive 'CCDC 2193503'
loop_
_audit_author_name
_audit_author_address
'Haitao Liu'
;Shandong Normal University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_audit_creation_date             2022-06-25
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H19 N S'
_chemical_formula_sum            'C19 H19 N S'
_chemical_formula_weight         293.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.4233(4)
_cell_length_b                   9.6651(5)
_cell_length_c                   18.0611(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.894(5)
_cell_angle_gamma                90.00
_cell_volume                     1589.69(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8247
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.6180
_cell_measurement_theta_min      2.4090
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12903
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9251
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0243047000
_diffrn_orient_matrix_UB_12      0.0085905000
_diffrn_orient_matrix_UB_13      -0.0402942000
_diffrn_orient_matrix_UB_21      -0.0660991000
_diffrn_orient_matrix_UB_22      0.0302115000
_diffrn_orient_matrix_UB_23      0.0041717000
_diffrn_orient_matrix_UB_31      0.0332894000
_diffrn_orient_matrix_UB_32      0.0663053000
_diffrn_orient_matrix_UB_33      0.0033441000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2562
_reflns_number_total             3012
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0100(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.5446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29121(17) 0.40371(16) 0.89318(9) 0.0229(3) Uani 1 1 d . . .
C2 C 0.2747(2) 0.40395(18) 0.96892(9) 0.0309(4) Uani 1 1 d . . .
H2 H 0.3573 0.4208 1.0108 0.037 Uiso 1 1 calc R . .
C3 C 0.1404(2) 0.38002(19) 0.98191(10) 0.0348(4) Uani 1 1 d . . .
H3 H 0.1303 0.3798 1.0329 0.042 Uiso 1 1 calc R . .
C4 C 0.01701(19) 0.35575(19) 0.92042(10) 0.0326(4) Uani 1 1 d . . .
H4 H -0.0756 0.3379 0.9303 0.039 Uiso 1 1 calc R . .
C5 C 0.02906(18) 0.35760(17) 0.84659(9) 0.0264(4) Uani 1 1 d . . .
H5 H -0.0555 0.3416 0.8056 0.032 Uiso 1 1 calc R . .
C6 C 0.16651(16) 0.38319(15) 0.83036(9) 0.0217(3) Uani 1 1 d . . .
C7 C 0.18666(16) 0.39168(15) 0.75441(8) 0.0207(3) Uani 1 1 d . . .
C8 C 0.32591(17) 0.41512(16) 0.74719(9) 0.0227(3) Uani 1 1 d . . .
H8 H 0.3433 0.4222 0.6978 0.027 Uiso 1 1 calc R . .
C9 C 0.44353(17) 0.42877(16) 0.81343(9) 0.0230(3) Uani 1 1 d . . .
C10 C 0.05748(17) 0.37110(17) 0.68497(9) 0.0255(4) Uani 1 1 d . . .
H10 H -0.0304 0.4156 0.6963 0.031 Uiso 1 1 calc R . .
C11 C 0.02487(18) 0.21616(18) 0.67278(10) 0.0320(4) Uani 1 1 d . . .
H11A H 0.1110 0.1691 0.6637 0.048 Uiso 1 1 calc R . .
H11B H -0.0592 0.2031 0.6283 0.048 Uiso 1 1 calc R . .
H11C H 0.0019 0.1773 0.7185 0.048 Uiso 1 1 calc R . .
C12 C 0.0807(2) 0.4378(2) 0.61219(10) 0.0365(4) Uani 1 1 d . . .
H12A H 0.1102 0.5345 0.6226 0.055 Uiso 1 1 calc R . .
H12B H -0.0111 0.4338 0.5716 0.055 Uiso 1 1 calc R . .
H12C H 0.1577 0.3877 0.5957 0.055 Uiso 1 1 calc R . .
C13 C 0.63036(16) 0.43131(17) 0.71400(9) 0.0259(4) Uani 1 1 d . . .
C14 C 0.66368(18) 0.53887(17) 0.67086(10) 0.0287(4) Uani 1 1 d . . .
H14 H 0.6763 0.6297 0.6916 0.034 Uiso 1 1 calc R . .
C15 C 0.67879(19) 0.51490(18) 0.59739(10) 0.0322(4) Uani 1 1 d . . .
H15 H 0.7047 0.5892 0.5690 0.039 Uiso 1 1 calc R . .
C16 C 0.65648(17) 0.38382(18) 0.56485(10) 0.0302(4) Uani 1 1 d . . .
C17 C 0.62050(19) 0.27757(18) 0.60819(11) 0.0359(4) Uani 1 1 d . . .
H17 H 0.6032 0.1876 0.5866 0.043 Uiso 1 1 calc R . .
C18 C 0.60921(19) 0.29939(18) 0.68203(11) 0.0351(4) Uani 1 1 d . . .
H18 H 0.5870 0.2243 0.7111 0.042 Uiso 1 1 calc R . .
C19 C 0.6738(2) 0.3559(2) 0.48533(11) 0.0436(5) Uani 1 1 d . . .
H19A H 0.7739 0.3238 0.4888 0.065 Uiso 1 1 calc R . .
H19B H 0.6552 0.4412 0.4550 0.065 Uiso 1 1 calc R . .
H19C H 0.6035 0.2847 0.4606 0.065 Uiso 1 1 calc R . .
N1 N 0.42953(14) 0.42445(14) 0.88399(7) 0.0251(3) Uani 1 1 d . . .
S1 S 0.62790(4) 0.46072(5) 0.81080(2) 0.03376(16) Uani 1 1 d . . .


_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
C1 C2 1.416(2) . ?
C1 C6 1.422(2) . ?
C1 N1 1.370(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.365(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.421(2) . ?
C6 C7 1.435(2) . ?
C7 C8 1.370(2) . ?
C7 C10 1.520(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.413(2) . ?
C9 N1 1.315(2) . ?
C9 S1 1.7772(16) . ?
C10 H10 1.0000 . ?
C10 C11 1.533(2) . ?
C10 C12 1.529(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.383(2) . ?
C13 C18 1.393(2) . ?
C13 S1 1.7774(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 C17 1.385(2) . ?
C16 C19 1.511(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C2 C1 C6 119.84(14) . . ?
N1 C1 C2 117.44(14) . . ?
N1 C1 C6 122.71(14) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.19(16) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.51(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.59(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.80(15) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 118.00(14) . . ?
C5 C6 C1 118.02(14) . . ?
C5 C6 C7 123.97(14) . . ?
C6 C7 C10 120.44(13) . . ?
C8 C7 C6 117.75(14) . . ?
C8 C7 C10 121.78(14) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.79(14) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 S1 123.59(12) . . ?
N1 C9 C8 124.43(14) . . ?
N1 C9 S1 111.94(11) . . ?
C7 C10 H10 107.7 . . ?
C7 C10 C11 109.56(13) . . ?
C7 C10 C12 113.15(14) . . ?
C11 C10 H10 107.7 . . ?
C12 C10 H10 107.7 . . ?
C12 C10 C11 110.84(14) . . ?
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 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.93(16) . . ?
C14 C13 S1 119.75(13) . . ?
C18 C13 S1 121.17(13) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.43(15) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.94(16) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C19 121.55(17) . . ?
C17 C16 C15 117.99(16) . . ?
C17 C16 C19 120.45(16) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.55(16) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.12(16) . . ?
C17 C18 H18 119.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 N1 C1 117.22(13) . . ?
C9 S1 C13 104.98(7) . . ?

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
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C7 C8 1.9(2) . . . . ?
C1 C6 C7 C10 -179.83(14) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
C2 C1 C6 C7 176.45(14) . . . . ?
C2 C1 N1 C9 -177.78(14) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C4 C5 C6 C7 -177.65(15) . . . . ?
C5 C6 C7 C8 -179.15(15) . . . . ?
C5 C6 C7 C10 -0.8(2) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C6 C1 N1 C9 1.9(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C6 C7 C10 C11 -78.71(17) . . . . ?
C6 C7 C10 C12 157.07(15) . . . . ?
C7 C8 C9 N1 -2.0(2) . . . . ?
C7 C8 C9 S1 -179.44(12) . . . . ?
C8 C7 C10 C11 99.55(17) . . . . ?
C8 C7 C10 C12 -24.7(2) . . . . ?
C8 C9 N1 C1 0.8(2) . . . . ?
C8 C9 S1 C13 -12.62(16) . . . . ?
C10 C7 C8 C9 -177.76(14) . . . . ?
C13 C14 C15 C16 2.0(3) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C13 S1 C9 117.14(14) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C14 C15 C16 C19 -179.46(16) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C13 1.7(3) . . . . ?
C18 C13 C14 C15 -1.3(2) . . . . ?
C18 C13 S1 C9 -67.34(15) . . . . ?
C19 C16 C17 C18 177.65(16) . . . . ?
N1 C1 C2 C3 -178.18(15) . . . . ?
N1 C1 C6 C5 177.76(14) . . . . ?
N1 C1 C6 C7 -3.2(2) . . . . ?
N1 C9 S1 C13 169.65(12) . . . . ?
S1 C9 N1 C1 178.47(11) . . . . ?
S1 C13 C14 C15 174.30(13) . . . . ?
S1 C13 C18 C17 -176.03(13) . . . . ?

_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.714

