# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_mo_1524_cg_0m
_database_code_depnum_ccdc_archive 'CCDC 2130699'
loop_
_audit_author_name
_audit_author_address
'Yanjun Li'
;Goettingen University
Germany
;
_audit_update_record             
;
2021-12-23 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-06

loop_
_audit_author_email
?
'cgolz@gwdg.de '
Lutz.Ackermann@chemie.uni-goettingen.de
_audit_creation_method           
;
FinalCif V92 by Daniel Kratzert, Freiburg 2021,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C23 H22 O3 S'
_chemical_formula_moiety         'C23 H22 O3 S'
_chemical_formula_weight         378.46
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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:
 C22(H22A,H22B), C45(H45A,H45B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C17(H17), C18(H18), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32),
  C33(H33), C34(H34), C35(H35), C38(H38), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.2748(7)
_cell_length_b                   12.2905(9)
_cell_length_c                   12.5063(12)
_cell_angle_alpha                63.599(2)
_cell_angle_beta                 79.446(2)
_cell_angle_gamma                75.302(2)
_cell_volume                     965.60(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.905
_cell_measurement_theta_max      28.709
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7277
_exptl_absorpt_correction_T_max  0.7565
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0708 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.9619.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.987
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            73464
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         28.732
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9983
_reflns_number_gt                9720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999
_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.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2021.4-0'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+0.1943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         9983
_refine_ls_number_parameters     493
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.008(10)
_refine_ls_abs_structure_details 
;
 Flack x determined using 4698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
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'

_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_
_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 -0.01876(6) 0.70486(4) 0.62860(4) 0.01941(9) Uani 1 1 d . . . . .
O1 O 0.0364(2) 1.11857(12) 0.75697(12) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.50985(18) 1.06048(11) 0.21674(11) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.5997(2) 0.85464(12) 0.32199(12) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.2061(2) 0.61232(15) 0.67595(14) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.2788(3) 0.49888(15) 0.66849(15) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.209675 0.470433 0.631781 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4513(3) 0.42739(16) 0.71431(16) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.499334 0.350212 0.709287 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5533(3) 0.46886(17) 0.76739(17) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.669555 0.419135 0.800740 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4850(3) 0.58348(16) 0.77167(16) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.557080 0.612296 0.806332 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3125(2) 0.65676(15) 0.72595(14) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.2416(2) 0.78000(15) 0.73117(15) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.1484(2) 0.78495(16) 0.84037(15) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.0840(2) 0.90142(16) 0.84732(15) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.0011(3) 0.90492(18) 0.95769(17) 0.0216(3) Uani 1 1 d . . . . .
H10 H -0.040458 0.982295 0.962938 0.026 Uiso 1 1 calc R U . . .
C11 C -0.0197(3) 0.79765(19) 1.05705(16) 0.0239(4) Uani 1 1 d . . . . .
H11 H -0.075399 0.801133 1.130632 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0414(3) 0.68219(18) 1.05044(16) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.026359 0.608231 1.119556 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1225(2) 0.67616(16) 0.94454(16) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.161783 0.597879 0.941053 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1089(2) 1.01172(16) 0.74238(16) 0.0182(3) Uani 1 1 d . . . . .
C15 C 0.1998(2) 1.00583(15) 0.63877(15) 0.0174(3) Uani 1 1 d . . . . .
H15 H 0.216558 1.079974 0.570329 0.021 Uiso 1 1 calc R U . . .
C16 C 0.2697(2) 0.88899(15) 0.63262(14) 0.0152(3) Uani 1 1 d . . . . .
C17 C 0.3746(2) 0.88336(15) 0.52288(15) 0.0159(3) Uani 1 1 d . . . . .
H17 H 0.423850 0.803010 0.525294 0.019 Uiso 1 1 calc R U . . .
C18 C 0.4086(2) 0.97887(15) 0.41960(15) 0.0174(3) Uani 1 1 d . . . . .
H18 H 0.363715 1.061392 0.412066 0.021 Uiso 1 1 calc R U . . .
C19 C 0.5162(2) 0.95536(15) 0.31766(15) 0.0164(3) Uani 1 1 d . . . . .
C20 C -0.0957(3) 0.62729(18) 0.55687(18) 0.0239(4) Uani 1 1 d . . . . .
H20A H 0.001614 0.618875 0.494074 0.036 Uiso 1 1 calc R U . . .
H20B H -0.215884 0.675826 0.521197 0.036 Uiso 1 1 calc R U . . .
H20C H -0.114847 0.544961 0.616307 0.036 Uiso 1 1 calc R U . . .
C21 C 0.0524(3) 1.23189(18) 0.6550(2) 0.0311(4) Uani 1 1 d . . . . .
H21A H -0.009453 1.236652 0.589293 0.047 Uiso 1 1 calc R U . . .
H21B H 0.187397 1.235326 0.630159 0.047 Uiso 1 1 calc R U . . .
H21C H -0.009739 1.301688 0.675363 0.047 Uiso 1 1 calc R U . . .
C22 C 0.6045(3) 1.04415(18) 0.11060(16) 0.0267(4) Uani 1 1 d . . . . .
H22A H 0.548799 0.985782 0.097615 0.032 Uiso 1 1 calc R U . . .
H22B H 0.741983 1.009628 0.120752 0.032 Uiso 1 1 calc R U . . .
C23 C 0.5782(3) 1.16845(18) 0.00479(16) 0.0245(4) Uani 1 1 d . . . . .
H23A H 0.632367 1.158108 -0.068624 0.037 Uiso 1 1 calc R U . . .
H23B H 0.643190 1.223444 0.015203 0.037 Uiso 1 1 calc R U . . .
H23C H 0.441881 1.204691 -0.001046 0.037 Uiso 1 1 calc R U . . .
S2 S 0.31093(6) 0.33187(4) 0.32841(4) 0.02323(10) Uani 1 1 d . . . . .
O4 O 1.08509(19) -0.01808(11) 0.21412(12) 0.0224(3) Uani 1 1 d . . . . .
O5 O 0.60589(19) -0.08514(11) 0.79749(11) 0.0209(3) Uani 1 1 d . . . . .
O6 O 0.5414(2) 0.12205(13) 0.73440(12) 0.0270(3) Uani 1 1 d . . . . .
C24 C 0.4673(2) 0.42054(15) 0.33109(15) 0.0175(3) Uani 1 1 d . . . . .
C25 C 0.6665(2) 0.38764(14) 0.31541(14) 0.0158(3) Uani 1 1 d . . . . .
C26 C 0.7775(2) 0.46155(15) 0.32258(15) 0.0181(3) Uani 1 1 d . . . . .
H26 H 0.912400 0.441074 0.310904 0.022 Uiso 1 1 calc R U . . .
C27 C 0.6943(3) 0.56451(16) 0.34647(17) 0.0219(3) Uani 1 1 d . . . . .
H27 H 0.772014 0.613673 0.350949 0.026 Uiso 1 1 calc R U . . .
C28 C 0.4977(3) 0.59491(17) 0.36368(17) 0.0236(4) Uani 1 1 d . . . . .
H28 H 0.440105 0.664264 0.381281 0.028 Uiso 1 1 calc R U . . .
C29 C 0.3857(3) 0.52399(17) 0.35516(17) 0.0220(3) Uani 1 1 d . . . . .
H29 H 0.250851 0.545970 0.365856 0.026 Uiso 1 1 calc R U . . .
C30 C 0.7678(2) 0.27740(14) 0.29131(14) 0.0148(3) Uani 1 1 d . . . . .
C31 C 0.8523(2) 0.29679(15) 0.17292(15) 0.0156(3) Uani 1 1 d . . . . .
C32 C 0.8315(2) 0.41621(16) 0.07509(16) 0.0185(3) Uani 1 1 d . . . . .
H32 H 0.759017 0.486027 0.087969 0.022 Uiso 1 1 calc R U . . .
C33 C 0.9141(3) 0.43209(17) -0.03715(16) 0.0217(3) Uani 1 1 d . . . . .
H33 H 0.899056 0.512579 -0.100966 0.026 Uiso 1 1 calc R U . . .
C34 C 1.0213(3) 0.32977(18) -0.05853(16) 0.0232(4) Uani 1 1 d . . . . .
H34 H 1.078511 0.341684 -0.136577 0.028 Uiso 1 1 calc R U . . .
C35 C 1.0434(2) 0.21275(17) 0.03304(16) 0.0205(3) Uani 1 1 d . . . . .
H35 H 1.115481 0.144177 0.017895 0.025 Uiso 1 1 calc R U . . .
C36 C 0.9592(2) 0.19401(16) 0.14986(15) 0.0165(3) Uani 1 1 d . . . . .
C37 C 0.9790(2) 0.07340(15) 0.24634(16) 0.0172(3) Uani 1 1 d . . . . .
C38 C 0.8960(2) 0.05577(15) 0.35840(16) 0.0172(3) Uani 1 1 d . . . . .
H38 H 0.909193 -0.025440 0.421005 0.021 Uiso 1 1 calc R U . . .
C39 C 0.7894(2) 0.15865(15) 0.38218(15) 0.0157(3) Uani 1 1 d . . . . .
C40 C 0.7043(2) 0.13986(15) 0.50349(15) 0.0166(3) Uani 1 1 d . . . . .
H40 H 0.648779 0.212511 0.515960 0.020 Uiso 1 1 calc R U . . .
C41 C 0.6962(2) 0.03204(16) 0.59816(15) 0.0183(3) Uani 1 1 d . . . . .
H41 H 0.747798 -0.043766 0.590881 0.022 Uiso 1 1 calc R U . . .
C42 C 0.6064(2) 0.03133(16) 0.71450(15) 0.0186(3) Uani 1 1 d . . . . .
C43 C 0.3466(3) 0.3527(2) 0.1742(2) 0.0284(4) Uani 1 1 d . . . . .
H43A H 0.338563 0.440950 0.121314 0.043 Uiso 1 1 calc R U . . .
H43B H 0.248050 0.322155 0.157519 0.043 Uiso 1 1 calc R U . . .
H43C H 0.472623 0.306455 0.160087 0.043 Uiso 1 1 calc R U . . .
C44 C 1.0923(3) -0.14275(16) 0.30124(17) 0.0217(3) Uani 1 1 d . . . . .
H44A H 1.167172 -0.199490 0.266594 0.033 Uiso 1 1 calc R U . . .
H44B H 0.962583 -0.159077 0.325956 0.033 Uiso 1 1 calc R U . . .
H44C H 1.152098 -0.155354 0.371067 0.033 Uiso 1 1 calc R U . . .
C45 C 0.5298(3) -0.09654(19) 0.91668(16) 0.0247(4) Uani 1 1 d . . . . .
H45A H 0.395982 -0.051340 0.915262 0.030 Uiso 1 1 calc R U . . .
H45B H 0.605579 -0.061320 0.947108 0.030 Uiso 1 1 calc R U . . .
C46 C 0.5404(3) -0.2327(2) 0.99595(18) 0.0326(5) Uani 1 1 d . . . . .
H46A H 0.456097 -0.264770 0.969145 0.049 Uiso 1 1 calc R U . . .
H46B H 0.500231 -0.244250 1.078897 0.049 Uiso 1 1 calc R U . . .
H46C H 0.671797 -0.277368 0.991316 0.049 Uiso 1 1 calc R U . . .


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 C1 1.7696(17) . ?
S1 C20 1.8007(18) . ?
O1 C14 1.365(2) . ?
O1 C21 1.424(2) . ?
O2 C19 1.344(2) . ?
O2 C22 1.452(2) . ?
O3 C19 1.215(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C6 C7 1.498(2) . ?
C7 C8 1.429(2) . ?
C7 C16 1.390(2) . ?
C8 C9 1.425(2) . ?
C8 C13 1.418(2) . ?
C9 C10 1.416(2) . ?
C9 C14 1.431(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.410(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.428(2) . ?
C16 C17 1.464(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.338(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.473(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.506(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
S2 C24 1.7772(17) . ?
S2 C43 1.806(2) . ?
O4 C37 1.3676(19) . ?
O4 C44 1.426(2) . ?
O5 C42 1.344(2) . ?
O5 C45 1.449(2) . ?
O6 C42 1.210(2) . ?
C24 C25 1.404(2) . ?
C24 C29 1.397(2) . ?
C25 C26 1.399(2) . ?
C25 C30 1.498(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.392(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.433(2) . ?
C30 C39 1.386(2) . ?
C31 C32 1.426(2) . ?
C31 C36 1.424(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.370(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.409(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.375(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.417(2) . ?
C36 C37 1.428(2) . ?
C37 C38 1.365(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.429(2) . ?
C39 C40 1.468(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.334(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.479(2) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45 C46 1.508(3) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
C1 S1 C20 103.13(8) . . ?
C14 O1 C21 117.01(15) . . ?
C19 O2 C22 114.68(13) . . ?
C2 C1 S1 123.73(13) . . ?
C2 C1 C6 119.62(15) . . ?
C6 C1 S1 116.64(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.59(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.92(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.83(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.13(17) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 120.86(15) . . ?
C5 C6 C1 118.84(15) . . ?
C5 C6 C7 120.30(15) . . ?
C8 C7 C6 119.27(14) . . ?
C16 C7 C6 121.05(14) . . ?
C16 C7 C8 119.65(14) . . ?
C9 C8 C7 119.84(15) . . ?
C13 C8 C7 121.79(15) . . ?
C13 C8 C9 118.34(15) . . ?
C8 C9 C14 118.67(15) . . ?
C10 C9 C8 119.44(16) . . ?
C10 C9 C14 121.87(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.62(17) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.25(16) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.32(17) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.02(16) . . ?
C12 C13 H13 119.5 . . ?
O1 C14 C9 114.20(15) . . ?
O1 C14 C15 124.85(16) . . ?
C15 C14 C9 120.95(15) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.47(15) . . ?
C16 C15 H15 119.8 . . ?
C7 C16 C15 120.34(15) . . ?
C7 C16 C17 119.64(14) . . ?
C15 C16 C17 120.01(15) . . ?
C16 C17 H17 116.4 . . ?
C18 C17 C16 127.19(15) . . ?
C18 C17 H17 116.4 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.63(15) . . ?
C19 C18 H18 120.2 . . ?
O2 C19 C18 111.32(14) . . ?
O3 C19 O2 123.35(16) . . ?
O3 C19 C18 125.33(15) . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 110.0 . . ?
O2 C22 H22B 110.0 . . ?
O2 C22 C23 108.42(15) . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 S2 C43 102.13(9) . . ?
C37 O4 C44 117.12(14) . . ?
C42 O5 C45 115.27(14) . . ?
C25 C24 S2 122.82(13) . . ?
C29 C24 S2 117.51(13) . . ?
C29 C24 C25 119.61(16) . . ?
C24 C25 C30 123.70(15) . . ?
C26 C25 C24 118.46(15) . . ?
C26 C25 C30 117.83(14) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.34(16) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.66(16) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.78(16) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 H29 119.4 . . ?
C28 C29 C24 121.13(17) . . ?
C28 C29 H29 119.4 . . ?
C31 C30 C25 118.84(14) . . ?
C39 C30 C25 121.32(14) . . ?
C39 C30 C31 119.75(14) . . ?
C32 C31 C30 122.42(15) . . ?
C36 C31 C30 119.72(14) . . ?
C36 C31 C32 117.86(15) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 C31 121.18(16) . . ?
C33 C32 H32 119.4 . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.41(16) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.32(17) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.30(16) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C37 118.66(14) . . ?
C35 C36 C31 119.93(15) . . ?
C35 C36 C37 121.41(15) . . ?
O4 C37 C36 113.63(14) . . ?
C38 C37 O4 125.23(15) . . ?
C38 C37 C36 121.14(15) . . ?
C37 C38 H38 119.8 . . ?
C37 C38 C39 120.44(15) . . ?
C39 C38 H38 119.8 . . ?
C30 C39 C38 120.29(15) . . ?
C30 C39 C40 119.36(14) . . ?
C38 C39 C40 120.34(14) . . ?
C39 C40 H40 116.4 . . ?
C41 C40 C39 127.19(15) . . ?
C41 C40 H40 116.4 . . ?
C40 C41 H41 120.2 . . ?
C40 C41 C42 119.54(15) . . ?
C42 C41 H41 120.2 . . ?
O5 C42 C41 110.83(14) . . ?
O6 C42 O5 123.55(16) . . ?
O6 C42 C41 125.62(16) . . ?
S2 C43 H43A 109.5 . . ?
S2 C43 H43B 109.5 . . ?
S2 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O5 C45 H45A 110.2 . . ?
O5 C45 H45B 110.2 . . ?
O5 C45 C46 107.35(17) . . ?
H45A C45 H45B 108.5 . . ?
C46 C45 H45A 110.2 . . ?
C46 C45 H45B 110.2 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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 C1 C2 C3 -175.94(13) . . . . ?
S1 C1 C6 C5 175.92(13) . . . . ?
S1 C1 C6 C7 -3.6(2) . . . . ?
O1 C14 C15 C16 -179.64(16) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C7 C8 99.15(18) . . . . ?
C1 C6 C7 C16 -82.6(2) . . . . ?
C2 C1 C6 C5 -2.7(2) . . . . ?
C2 C1 C6 C7 177.79(15) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -179.86(16) . . . . ?
C5 C6 C7 C8 -80.3(2) . . . . ?
C5 C6 C7 C16 97.96(19) . . . . ?
C6 C1 C2 C3 2.6(2) . . . . ?
C6 C7 C8 C9 178.64(15) . . . . ?
C6 C7 C8 C13 0.6(2) . . . . ?
C6 C7 C16 C15 179.47(15) . . . . ?
C6 C7 C16 C17 -1.7(2) . . . . ?
C7 C8 C9 C10 -176.59(15) . . . . ?
C7 C8 C9 C14 2.1(2) . . . . ?
C7 C8 C13 C12 176.62(16) . . . . ?
C7 C16 C17 C18 177.74(17) . . . . ?
C8 C7 C16 C15 -2.3(2) . . . . ?
C8 C7 C16 C17 176.60(15) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C14 O1 177.71(15) . . . . ?
C8 C9 C14 C15 -2.8(2) . . . . ?
C9 C8 C13 C12 -1.5(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C14 C15 C16 0.9(3) . . . . ?
C10 C9 C14 O1 -3.6(2) . . . . ?
C10 C9 C14 C15 175.94(16) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C13 C8 C9 C10 1.5(2) . . . . ?
C13 C8 C9 C14 -179.72(16) . . . . ?
C14 C9 C10 C11 -179.50(17) . . . . ?
C14 C15 C16 C7 1.7(2) . . . . ?
C14 C15 C16 C17 -177.18(16) . . . . ?
C15 C16 C17 C18 -3.4(3) . . . . ?
C16 C7 C8 C9 0.3(2) . . . . ?
C16 C7 C8 C13 -177.74(15) . . . . ?
C16 C17 C18 C19 -179.50(16) . . . . ?
C17 C18 C19 O2 169.83(15) . . . . ?
C17 C18 C19 O3 -9.7(3) . . . . ?
C19 O2 C22 C23 177.64(15) . . . . ?
C20 S1 C1 C2 -7.42(16) . . . . ?
C20 S1 C1 C6 173.99(13) . . . . ?
C21 O1 C14 C9 -178.52(16) . . . . ?
C21 O1 C14 C15 2.0(3) . . . . ?
C22 O2 C19 O3 2.6(2) . . . . ?
C22 O2 C19 C18 -176.96(15) . . . . ?
S2 C24 C25 C26 -178.13(13) . . . . ?
S2 C24 C25 C30 1.9(2) . . . . ?
S2 C24 C29 C28 177.34(15) . . . . ?
O4 C37 C38 C39 179.44(16) . . . . ?
C24 C25 C26 C27 1.0(2) . . . . ?
C24 C25 C30 C31 105.87(19) . . . . ?
C24 C25 C30 C39 -77.5(2) . . . . ?
C25 C24 C29 C28 0.1(3) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C25 C30 C31 C32 -4.8(2) . . . . ?
C25 C30 C31 C36 176.17(14) . . . . ?
C25 C30 C39 C38 -176.39(15) . . . . ?
C25 C30 C39 C40 2.7(2) . . . . ?
C26 C25 C30 C31 -74.1(2) . . . . ?
C26 C25 C30 C39 102.53(19) . . . . ?
C26 C27 C28 C29 -1.0(3) . . . . ?
C27 C28 C29 C24 0.9(3) . . . . ?
C29 C24 C25 C26 -1.0(2) . . . . ?
C29 C24 C25 C30 178.97(16) . . . . ?
C30 C25 C26 C27 -179.03(15) . . . . ?
C30 C31 C32 C33 179.89(16) . . . . ?
C30 C31 C36 C35 -179.83(15) . . . . ?
C30 C31 C36 C37 0.1(2) . . . . ?
C30 C39 C40 C41 173.42(17) . . . . ?
C31 C30 C39 C38 0.2(2) . . . . ?
C31 C30 C39 C40 179.29(14) . . . . ?
C31 C32 C33 C34 0.4(3) . . . . ?
C31 C36 C37 O4 -179.70(15) . . . . ?
C31 C36 C37 C38 0.8(2) . . . . ?
C32 C31 C36 C35 1.1(2) . . . . ?
C32 C31 C36 C37 -179.03(15) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C34 C35 C36 C37 179.64(16) . . . . ?
C35 C36 C37 O4 0.2(2) . . . . ?
C35 C36 C37 C38 -179.35(16) . . . . ?
C36 C31 C32 C33 -1.0(2) . . . . ?
C36 C37 C38 C39 -1.1(2) . . . . ?
C37 C38 C39 C30 0.6(2) . . . . ?
C37 C38 C39 C40 -178.46(15) . . . . ?
C38 C39 C40 C41 -7.5(3) . . . . ?
C39 C30 C31 C32 178.50(15) . . . . ?
C39 C30 C31 C36 -0.5(2) . . . . ?
C39 C40 C41 C42 179.15(15) . . . . ?
C40 C41 C42 O5 177.83(16) . . . . ?
C40 C41 C42 O6 -2.2(3) . . . . ?
C42 O5 C45 C46 179.74(15) . . . . ?
C43 S2 C24 C25 -67.11(16) . . . . ?
C43 S2 C24 C29 115.74(15) . . . . ?
C44 O4 C37 C36 -172.48(15) . . . . ?
C44 O4 C37 C38 7.0(2) . . . . ?
C45 O5 C42 O6 -3.1(3) . . . . ?
C45 O5 C42 C41 176.91(14) . . . . ?

####################################################################### 
# 
# 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_mo_1565_cg_0m
_database_code_depnum_ccdc_archive 'CCDC 2144688'
loop_
_audit_author_name
_audit_author_address
'Yanjun Li'
;Goettingen University
Germany
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_audit_creation_date             2022-01-26

loop_
_audit_author_email
yan-cheng.liou@chemie.uni-goettingen.de
Lutz.Ackermann@chemie.uni-goettingen.de
'cgolz@gwdg.de '
_audit_creation_method           
;
FinalCif V97 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H20 N2 O S'
_chemical_formula_moiety         'C20 H20 N2 O S'
_chemical_formula_weight         336.44
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.0831(4)
_cell_length_b                   6.8389(3)
_cell_length_c                   12.0729(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.142(2)
_cell_angle_gamma                90
_cell_volume                     864.48(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9719
_cell_measurement_theta_min      3.042
_cell_measurement_theta_max      32.919
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystallized from a mixture of ethyl acetate, dichloromethane and hexane by fullevaporation.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.413
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.9725.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            30575
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         33.459
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6087
_reflns_number_gt                5968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.853
_reflns_Friedel_fraction_full    0.997
_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.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2021.4-0'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.0813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6087
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_abs_structure_details 
;
 Flack x determined using 2601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.70220(2) 0.70761(4) 0.35193(2) 0.01945(7) Uani 1 1 d . . . . .
O1 O 0.87827(8) 0.34601(16) 0.70583(8) 0.02481(18) Uani 1 1 d . . . . .
N1 N 0.60663(9) 0.29391(14) 0.28647(8) 0.01633(16) Uani 1 1 d . . . . .
N2 N 0.76010(9) 0.25477(15) 0.81848(8) 0.01891(18) Uani 1 1 d . . . . .
C1 C 0.78509(10) 0.51950(16) 0.30616(9) 0.01621(18) Uani 1 1 d . . . . .
C2 C 0.72951(10) 0.33398(16) 0.27823(9) 0.01570(17) Uani 1 1 d . . . . .
C3 C 0.79301(11) 0.18531(18) 0.24017(10) 0.0209(2) Uani 1 1 d . . . . .
H3 H 0.754259 0.060420 0.220929 0.025 Uiso 1 1 calc R U . . .
C4 C 0.91290(11) 0.2197(2) 0.23036(10) 0.0240(2) Uani 1 1 d . . . . .
H4 H 0.956952 0.118026 0.205981 0.029 Uiso 1 1 calc R U . . .
C5 C 0.96757(11) 0.4042(2) 0.25659(10) 0.0235(2) Uani 1 1 d . . . . .
H5 H 1.048723 0.428822 0.248714 0.028 Uiso 1 1 calc R U . . .
C6 C 0.90502(11) 0.55278(19) 0.29412(10) 0.0211(2) Uani 1 1 d . . . . .
H6 H 0.943710 0.677973 0.311803 0.025 Uiso 1 1 calc R U . . .
C7 C 0.82797(16) 0.8165(3) 0.46969(15) 0.0411(4) Uani 1 1 d . . . . .
H7A H 0.891497 0.873861 0.438847 0.062 Uiso 1 1 calc R U . . .
H7B H 0.868706 0.716182 0.527915 0.062 Uiso 1 1 calc R U . . .
H7C H 0.792390 0.918908 0.506646 0.062 Uiso 1 1 calc R U . . .
C8 C 0.49701(10) 0.27038(17) 0.19165(9) 0.01630(17) Uani 1 1 d . . . . .
C9 C 0.39376(10) 0.24321(15) 0.23484(9) 0.01727(19) Uani 1 1 d . . . . .
C10 C 0.44563(10) 0.24832(16) 0.35982(9) 0.01819(19) Uani 1 1 d . . . . .
H10 H 0.399223 0.232670 0.412889 0.022 Uiso 1 1 calc R U . . .
C11 C 0.57546(10) 0.28013(17) 0.38960(9) 0.01612(17) Uani 1 1 d . . . . .
C12 C 0.67490(10) 0.29670(16) 0.50196(9) 0.01652(18) Uani 1 1 d . . . . .
H12 H 0.759131 0.320572 0.501383 0.020 Uiso 1 1 calc R U . . .
C13 C 0.65892(10) 0.28141(18) 0.60681(9) 0.01769(18) Uani 1 1 d . . . . .
H13 H 0.576600 0.260016 0.612820 0.021 Uiso 1 1 calc R U . . .
C14 C 0.77323(10) 0.29876(16) 0.71365(9) 0.01697(18) Uani 1 1 d . . . . .
C15 C 0.26984(10) 0.2227(2) 0.15365(10) 0.0215(2) Uani 1 1 d . . . . .
H15 H 0.198454 0.205870 0.179794 0.026 Uiso 1 1 calc R U . . .
C16 C 0.25394(11) 0.2275(2) 0.03492(10) 0.0238(2) Uani 1 1 d . . . . .
H16 H 0.170699 0.213358 -0.020418 0.029 Uiso 1 1 calc R U . . .
C17 C 0.35873(11) 0.25285(18) -0.00543(10) 0.0223(2) Uani 1 1 d . . . . .
H17 H 0.344894 0.254567 -0.087357 0.027 Uiso 1 1 calc R U . . .
C18 C 0.48146(11) 0.27530(18) 0.07224(9) 0.01903(19) Uani 1 1 d . . . . .
H18 H 0.552192 0.293328 0.045324 0.023 Uiso 1 1 calc R U . . .
C19 C 0.63937(11) 0.2258(2) 0.83982(10) 0.0213(2) Uani 1 1 d . . . . .
H19A H 0.608726 0.351447 0.859194 0.032 Uiso 1 1 calc R U . . .
H19B H 0.651939 0.134736 0.905317 0.032 Uiso 1 1 calc R U . . .
H19C H 0.576227 0.171772 0.769302 0.032 Uiso 1 1 calc R U . . .
C20 C 0.87294(12) 0.2611(2) 0.92309(10) 0.0272(2) Uani 1 1 d . . . . .
H20A H 0.946679 0.304335 0.901713 0.041 Uiso 1 1 calc R U . . .
H20B H 0.889605 0.130370 0.958083 0.041 Uiso 1 1 calc R U . . .
H20C H 0.858400 0.352759 0.979814 0.041 Uiso 1 1 calc R U . . .


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 C1 1.7712(11) . ?
S1 C7 1.7942(15) . ?
O1 C14 1.2413(13) . ?
N1 C2 1.4244(13) . ?
N1 C8 1.3785(13) . ?
N1 C11 1.4001(13) . ?
N2 C14 1.3544(13) . ?
N2 C19 1.4567(14) . ?
N2 C20 1.4578(15) . ?
C1 C2 1.4024(15) . ?
C1 C6 1.4022(14) . ?
C2 C3 1.3973(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3921(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3871(18) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.4168(14) . ?
C8 C18 1.3950(14) . ?
C9 C10 1.4281(15) . ?
C9 C15 1.4085(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3812(14) . ?
C11 C12 1.4448(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3385(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.4870(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3861(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.4098(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3843(16) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C1 S1 C7 101.59(6) . . ?
C8 N1 C2 124.54(9) . . ?
C8 N1 C11 108.87(8) . . ?
C11 N1 C2 126.55(9) . . ?
C14 N2 C19 125.58(9) . . ?
C14 N2 C20 118.59(10) . . ?
C19 N2 C20 115.32(9) . . ?
C2 C1 S1 120.01(8) . . ?
C6 C1 S1 121.38(9) . . ?
C6 C1 C2 118.59(10) . . ?
C1 C2 N1 120.79(9) . . ?
C3 C2 N1 118.64(10) . . ?
C3 C2 C1 120.56(10) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.19(12) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.37(11) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.79(10) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.48(11) . . ?
C5 C6 H6 119.8 . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 107.93(9) . . ?
N1 C8 C18 129.20(10) . . ?
C18 C8 C9 122.85(10) . . ?
C8 C9 C10 106.96(9) . . ?
C15 C9 C8 118.55(10) . . ?
C15 C9 C10 134.47(10) . . ?
C9 C10 H10 126.2 . . ?
C11 C10 C9 107.63(9) . . ?
C11 C10 H10 126.2 . . ?
N1 C11 C12 119.67(9) . . ?
C10 C11 N1 108.60(9) . . ?
C10 C11 C12 131.72(9) . . ?
C11 C12 H12 117.1 . . ?
C13 C12 C11 125.81(10) . . ?
C13 C12 H12 117.1 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.35(9) . . ?
C14 C13 H13 120.8 . . ?
O1 C14 N2 121.32(10) . . ?
O1 C14 C13 120.55(10) . . ?
N2 C14 C13 118.09(9) . . ?
C9 C15 H15 120.6 . . ?
C16 C15 C9 118.79(10) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.36(10) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.16(10) . . ?
C18 C17 H17 119.4 . . ?
C8 C18 H18 121.4 . . ?
C17 C18 C8 117.28(10) . . ?
C17 C18 H18 121.4 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C1 C2 N1 -0.19(13) . . . . ?
S1 C1 C2 C3 178.94(8) . . . . ?
S1 C1 C6 C5 -179.10(9) . . . . ?
N1 C2 C3 C4 179.60(10) . . . . ?
N1 C8 C9 C10 -0.85(12) . . . . ?
N1 C8 C9 C15 177.79(10) . . . . ?
N1 C8 C18 C17 -178.08(11) . . . . ?
N1 C11 C12 C13 -178.22(11) . . . . ?
C1 C2 C3 C4 0.45(16) . . . . ?
C2 N1 C8 C9 -176.91(10) . . . . ?
C2 N1 C8 C18 1.57(19) . . . . ?
C2 N1 C11 C10 177.32(11) . . . . ?
C2 N1 C11 C12 -3.55(17) . . . . ?
C2 C1 C6 C5 -0.70(15) . . . . ?
C2 C3 C4 C5 -1.24(16) . . . . ?
C3 C4 C5 C6 1.07(17) . . . . ?
C4 C5 C6 C1 -0.09(17) . . . . ?
C6 C1 C2 N1 -178.61(10) . . . . ?
C6 C1 C2 C3 0.52(15) . . . . ?
C7 S1 C1 C2 138.10(11) . . . . ?
C7 S1 C1 C6 -43.52(11) . . . . ?
C8 N1 C2 C1 107.53(12) . . . . ?
C8 N1 C2 C3 -71.62(15) . . . . ?
C8 N1 C11 C10 -0.17(13) . . . . ?
C8 N1 C11 C12 178.97(10) . . . . ?
C8 C9 C10 C11 0.75(12) . . . . ?
C8 C9 C15 C16 0.77(17) . . . . ?
C9 C8 C18 C17 0.19(18) . . . . ?
C9 C10 C11 N1 -0.37(12) . . . . ?
C9 C10 C11 C12 -179.36(11) . . . . ?
C9 C15 C16 C17 -0.18(19) . . . . ?
C10 C9 C15 C16 178.95(12) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 N1 C2 C1 -69.58(14) . . . . ?
C11 N1 C2 C3 111.27(12) . . . . ?
C11 N1 C8 C9 0.64(13) . . . . ?
C11 N1 C8 C18 179.11(11) . . . . ?
C11 C12 C13 C14 178.82(10) . . . . ?
C12 C13 C14 O1 7.24(17) . . . . ?
C12 C13 C14 N2 -170.42(10) . . . . ?
C15 C9 C10 C11 -177.58(13) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C8 0.44(18) . . . . ?
C18 C8 C9 C10 -179.44(11) . . . . ?
C18 C8 C9 C15 -0.80(17) . . . . ?
C19 N2 C14 O1 170.47(12) . . . . ?
C19 N2 C14 C13 -11.89(17) . . . . ?
C20 N2 C14 O1 -0.89(17) . . . . ?
C20 N2 C14 C13 176.75(11) . . . . ?

