# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_ami12
_database_code_depnum_ccdc_archive 'CCDC 2130650'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-12-23 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Cl3 N O'
_chemical_formula_weight         392.69

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'

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

_cell_length_a                   11.86860(7)
_cell_length_b                   11.86860(7)
_cell_length_c                   23.1699(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2826.53(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      19.69

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    0.494
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42952
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         0.879
_diffrn_reflns_theta_max         26.712
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7954
_reflns_number_gt                6443
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.2471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2565 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7954
_refine_ls_number_parameters     454
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
C11_1 C 0.6863(5) 1.1492(5) 0.5714(3) 0.0358(13) Uani 1 1 d . . . . .
C12_1 C 0.5703(7) 1.1085(7) 0.5441(3) 0.0503(16) Uani 1 1 d . . . . .
H12_1 H 0.521632 1.021146 0.530978 0.060 Uiso 1 1 calc R U . . .
C13_1 C 0.5215(8) 1.1930(8) 0.5351(3) 0.066(2) Uani 1 1 d . . . . .
H13_1 H 0.441220 1.162428 0.515307 0.079 Uiso 1 1 calc R U . . .
C14_1 C 0.5872(8) 1.3182(7) 0.5541(3) 0.0618(19) Uani 1 1 d . . . . .
H14_1 H 0.551126 1.373049 0.548796 0.074 Uiso 1 1 calc R U . . .
C15_1 C 0.7058(7) 1.3658(6) 0.5811(3) 0.0497(16) Uani 1 1 d . . . . .
C16_1 C 0.7785(9) 1.4968(8) 0.6006(4) 0.067(2) Uani 1 1 d . . . . .
H16_1 H 0.745599 1.553906 0.593535 0.080 Uiso 1 1 calc R U . . .
C17_1 C 0.8907(10) 1.5417(7) 0.6282(4) 0.078(3) Uani 1 1 d . . . . .
H17_1 H 0.936505 1.629696 0.640685 0.094 Uiso 1 1 calc R U . . .
C18_1 C 0.9422(7) 1.4599(8) 0.6391(4) 0.071(2) Uani 1 1 d . . . . .
H18_1 H 1.021852 1.492707 0.659598 0.086 Uiso 1 1 calc R U . . .
C19_1 C 0.8784(6) 1.3326(6) 0.6205(3) 0.0517(17) Uani 1 1 d . . . . .
H19_1 H 0.915482 1.279134 0.627716 0.062 Uiso 1 1 calc R U . . .
C20_1 C 0.7585(6) 1.2802(6) 0.5906(2) 0.0396(14) Uani 1 1 d . . . . .
C21_1 C 0.7416(6) 1.0608(6) 0.5785(3) 0.0443(15) Uani 1 1 d . . . . .
H21_1 H 0.787100 1.081761 0.616678 0.053 Uiso 1 1 calc R U . . .
C22_1 C 0.8436(8) 1.0784(7) 0.5318(3) 0.069(2) Uani 1 1 d . . . . .
H22A_1 H 0.919960 1.166817 0.535856 0.083 Uiso 1 1 calc R U . . .
H22B_1 H 0.873330 1.015456 0.539806 0.083 Uiso 1 1 calc R U . . .
C23_1 C 0.7978(11) 1.0609(11) 0.4713(4) 0.106(4) Uani 1 1 d . . . . .
H23A_1 H 0.870438 1.081046 0.445163 0.159 Uiso 1 1 calc R U . . .
H23B_1 H 0.763771 1.119409 0.463197 0.159 Uiso 1 1 calc R U . . .
H23C_1 H 0.728735 0.970579 0.465343 0.159 Uiso 1 1 calc R U . . .
C30_1 C 0.5696(6) 0.8725(6) 0.6266(3) 0.0357(12) Uani 1 1 d . . . . .
O30_1 O 0.5733(4) 0.9386(4) 0.6691(2) 0.0439(10) Uani 1 1 d . . . . .
N30_1 N 0.6407(5) 0.9226(5) 0.5801(2) 0.0407(12) Uani 1 1 d . . . . .
H30_1 H 0.627931 0.873136 0.549650 0.049 Uiso 1 1 calc R U . . .
C31_1 C 0.4857(5) 0.7270(5) 0.6276(3) 0.0336(12) Uani 1 1 d . . . . .
C32_1 C 0.3553(6) 0.6656(7) 0.6125(3) 0.0410(14) Uani 1 1 d . . . . .
C33_1 C 0.2765(6) 0.5312(7) 0.6135(3) 0.0504(18) Uani 1 1 d . . . . .
H33_1 H 0.187130 0.490982 0.603341 0.060 Uiso 1 1 calc R U . . .
C34_1 C 0.3316(7) 0.4581(6) 0.6297(3) 0.0507(17) Uani 1 1 d . . . . .
C35_1 C 0.4607(7) 0.5134(6) 0.6441(3) 0.0452(16) Uani 1 1 d . . . . .
H35_1 H 0.497481 0.461027 0.654174 0.054 Uiso 1 1 calc R U . . .
C36_1 C 0.5361(5) 0.6485(6) 0.6437(3) 0.0386(14) Uani 1 1 d . . . . .
Cl1_1 Cl 0.28666(18) 0.75866(19) 0.59261(8) 0.0588(5) Uani 1 1 d . . . . .
Cl2_1 Cl 0.2348(2) 0.28992(17) 0.63286(10) 0.0760(6) Uani 1 1 d . . . . .
Cl3_1 Cl 0.69817(16) 0.72116(17) 0.66371(9) 0.0564(4) Uani 1 1 d . . . . .
C11_2 C 0.8018(6) 0.7621(6) 0.4018(3) 0.0386(14) Uani 1 1 d . . . . .
C12_2 C 0.7902(7) 0.8259(7) 0.3552(3) 0.0565(19) Uani 1 1 d . . . . .
H12_2 H 0.710433 0.788371 0.334496 0.068 Uiso 1 1 calc R U . . .
C13_2 C 0.8969(9) 0.9489(8) 0.3368(4) 0.071(2) Uani 1 1 d . . . . .
H13_2 H 0.888453 0.992552 0.304120 0.086 Uiso 1 1 calc R U . . .
C14_2 C 1.0097(8) 1.0013(8) 0.3669(4) 0.071(2) Uani 1 1 d . . . . .
H14_2 H 1.081126 1.081533 0.354383 0.085 Uiso 1 1 calc R U . . .
C15_2 C 1.0242(7) 0.9418(7) 0.4155(4) 0.059(2) Uani 1 1 d . . . . .
C16_2 C 1.1434(8) 0.9980(9) 0.4475(6) 0.096(4) Uani 1 1 d . . . . .
H16_2 H 1.213974 1.079449 0.435580 0.115 Uiso 1 1 calc R U . . .
C17_2 C 1.1583(11) 0.9379(12) 0.4946(7) 0.120(4) Uani 1 1 d . . . . .
H17_2 H 1.239391 0.975197 0.514225 0.144 Uiso 1 1 calc R U . . .
C18_2 C 1.0550(8) 0.8231(10) 0.5135(5) 0.104(4) Uani 1 1 d . . . . .
H18_2 H 1.062769 0.784596 0.548082 0.125 Uiso 1 1 calc R U . . .
C19_2 C 0.9411(7) 0.7633(7) 0.4832(3) 0.0572(19) Uani 1 1 d . . . . .
H19_2 H 0.873337 0.680648 0.495577 0.069 Uiso 1 1 calc R U . . .
C20_2 C 0.9216(6) 0.8221(6) 0.4333(3) 0.0484(16) Uani 1 1 d . . . . .
C21_2 C 0.6960(5) 0.6247(6) 0.4163(3) 0.0379(13) Uani 1 1 d . . . . .
H21_2 H 0.711116 0.605756 0.456687 0.045 Uiso 1 1 calc R U . . .
C22_2 C 0.7036(6) 0.5250(6) 0.3764(3) 0.0450(15) Uani 1 1 d . . . . .
H22A_2 H 0.673911 0.532532 0.337456 0.054 Uiso 1 1 calc R U . . .
H22B_2 H 0.795826 0.547800 0.373203 0.054 Uiso 1 1 calc R U . . .
C23_2 C 0.6251(7) 0.3862(6) 0.3958(3) 0.0505(17) Uani 1 1 d . . . . .
H23A_2 H 0.640837 0.330483 0.369703 0.076 Uiso 1 1 calc R U . . .
H23B_2 H 0.532417 0.359280 0.395187 0.076 Uiso 1 1 calc R U . . .
H23C_2 H 0.650619 0.377965 0.435093 0.076 Uiso 1 1 calc R U . . .
C30_2 C 0.5177(6) 0.6435(6) 0.4579(3) 0.0390(13) Uani 1 1 d . . . . .
O30_2 O 0.5845(4) 0.7081(5) 0.4990(2) 0.0496(11) Uani 1 1 d . . . . .
N30_2 N 0.5643(5) 0.6067(5) 0.4136(2) 0.0382(12) Uani 1 1 d . . . . .
H30_2 H 0.515911 0.571588 0.382827 0.046 Uiso 1 1 calc R U . . .
C31_2 C 0.3742(6) 0.5960(6) 0.4557(3) 0.0382(14) Uani 1 1 d . . . . .
C32_2 C 0.3251(6) 0.6791(6) 0.4439(3) 0.0402(15) Uani 1 1 d . . . . .
C33_2 C 0.1943(7) 0.6392(7) 0.4452(3) 0.0480(16) Uani 1 1 d . . . . .
H33_2 H 0.164441 0.698607 0.437504 0.058 Uiso 1 1 calc R U . . .
C34_2 C 0.1068(6) 0.5090(7) 0.4581(3) 0.0494(16) Uani 1 1 d . . . . .
C35_2 C 0.1520(6) 0.4255(7) 0.4694(3) 0.0470(16) Uani 1 1 d . . . . .
H35_2 H 0.092046 0.337326 0.478563 0.056 Uiso 1 1 calc R U . . .
C36_2 C 0.2835(6) 0.4674(6) 0.4675(3) 0.0398(14) Uani 1 1 d . . . . .
Cl1_2 Cl 0.43574(18) 0.84144(17) 0.42911(8) 0.0584(5) Uani 1 1 d . . . . .
Cl2_2 Cl -0.05635(17) 0.4564(2) 0.45995(11) 0.0702(5) Uani 1 1 d . . . . .
Cl3_2 Cl 0.33312(18) 0.35689(17) 0.48225(8) 0.0561(5) 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
C11_1 C12_1 1.364(9) . ?
C11_1 C20_1 1.421(8) . ?
C11_1 C21_1 1.500(9) . ?
C12_1 C13_1 1.403(11) . ?
C12_1 H12_1 0.9500 . ?
C13_1 C14_1 1.360(11) . ?
C13_1 H13_1 0.9500 . ?
C14_1 C15_1 1.377(11) . ?
C14_1 H14_1 0.9500 . ?
C15_1 C16_1 1.423(10) . ?
C15_1 C20_1 1.451(9) . ?
C16_1 C17_1 1.325(13) . ?
C16_1 H16_1 0.9500 . ?
C17_1 C18_1 1.405(13) . ?
C17_1 H17_1 0.9500 . ?
C18_1 C19_1 1.378(10) . ?
C18_1 H18_1 0.9500 . ?
C19_1 C20_1 1.416(9) . ?
C19_1 H19_1 0.9500 . ?
C21_1 N30_1 1.470(8) . ?
C21_1 C22_1 1.558(9) . ?
C21_1 H21_1 1.0000 . ?
C22_1 C23_1 1.482(14) . ?
C22_1 H22A_1 0.9900 . ?
C22_1 H22B_1 0.9900 . ?
C23_1 H23A_1 0.9800 . ?
C23_1 H23B_1 0.9800 . ?
C23_1 H23C_1 0.9800 . ?
C30_1 O30_1 1.245(7) . ?
C30_1 N30_1 1.314(8) . ?
C30_1 C31_1 1.502(8) . ?
N30_1 H30_1 0.8800 . ?
C31_1 C32_1 1.386(9) . ?
C31_1 C36_1 1.387(9) . ?
C32_1 C33_1 1.388(10) . ?
C32_1 Cl1_1 1.731(7) . ?
C33_1 C34_1 1.375(10) . ?
C33_1 H33_1 0.9500 . ?
C34_1 C35_1 1.372(10) . ?
C34_1 Cl2_1 1.736(7) . ?
C35_1 C36_1 1.392(9) . ?
C35_1 H35_1 0.9500 . ?
C36_1 Cl3_1 1.732(6) . ?
C11_2 C12_2 1.365(9) . ?
C11_2 C20_2 1.431(9) . ?
C11_2 C21_2 1.517(8) . ?
C12_2 C13_2 1.438(11) . ?
C12_2 H12_2 0.9500 . ?
C13_2 C14_2 1.355(12) . ?
C13_2 H13_2 0.9500 . ?
C14_2 C15_2 1.385(13) . ?
C14_2 H14_2 0.9500 . ?
C15_2 C20_2 1.393(10) . ?
C15_2 C16_2 1.432(14) . ?
C16_2 C17_2 1.363(16) . ?
C16_2 H16_2 0.9500 . ?
C17_2 C18_2 1.371(14) . ?
C17_2 H17_2 0.9500 . ?
C18_2 C19_2 1.365(10) . ?
C18_2 H18_2 0.9500 . ?
C19_2 C20_2 1.428(10) . ?
C19_2 H19_2 0.9500 . ?
C21_2 N30_2 1.469(7) . ?
C21_2 C22_2 1.538(8) . ?
C21_2 H21_2 1.0000 . ?
C22_2 C23_2 1.500(9) . ?
C22_2 H22A_2 0.9900 . ?
C22_2 H22B_2 0.9900 . ?
C23_2 H23A_2 0.9800 . ?
C23_2 H23B_2 0.9800 . ?
C23_2 H23C_2 0.9800 . ?
C30_2 O30_2 1.231(7) . ?
C30_2 N30_2 1.337(7) . ?
C30_2 C31_2 1.504(8) . ?
N30_2 H30_2 0.8800 . ?
C31_2 C36_2 1.386(9) . ?
C31_2 C32_2 1.401(9) . ?
C32_2 C33_2 1.379(9) . ?
C32_2 Cl1_2 1.739(6) . ?
C33_2 C34_2 1.398(10) . ?
C33_2 H33_2 0.9500 . ?
C34_2 C35_2 1.367(10) . ?
C34_2 Cl2_2 1.712(7) . ?
C35_2 C36_2 1.382(9) . ?
C35_2 H35_2 0.9500 . ?
C36_2 Cl3_2 1.719(6) . ?

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
C12_1 C11_1 C20_1 118.8(6) . . ?
C12_1 C11_1 C21_1 121.4(6) . . ?
C20_1 C11_1 C21_1 119.7(5) . . ?
C11_1 C12_1 C13_1 121.4(6) . . ?
C11_1 C12_1 H12_1 119.3 . . ?
C13_1 C12_1 H12_1 119.3 . . ?
C14_1 C13_1 C12_1 121.0(7) . . ?
C14_1 C13_1 H13_1 119.5 . . ?
C12_1 C13_1 H13_1 119.5 . . ?
C13_1 C14_1 C15_1 120.4(7) . . ?
C13_1 C14_1 H14_1 119.8 . . ?
C15_1 C14_1 H14_1 119.8 . . ?
C14_1 C15_1 C16_1 121.9(7) . . ?
C14_1 C15_1 C20_1 119.4(6) . . ?
C16_1 C15_1 C20_1 118.6(7) . . ?
C17_1 C16_1 C15_1 122.0(8) . . ?
C17_1 C16_1 H16_1 119.0 . . ?
C15_1 C16_1 H16_1 119.0 . . ?
C16_1 C17_1 C18_1 120.4(7) . . ?
C16_1 C17_1 H17_1 119.8 . . ?
C18_1 C17_1 H17_1 119.8 . . ?
C19_1 C18_1 C17_1 120.7(8) . . ?
C19_1 C18_1 H18_1 119.6 . . ?
C17_1 C18_1 H18_1 119.6 . . ?
C18_1 C19_1 C20_1 121.0(7) . . ?
C18_1 C19_1 H19_1 119.5 . . ?
C20_1 C19_1 H19_1 119.5 . . ?
C19_1 C20_1 C11_1 123.9(6) . . ?
C19_1 C20_1 C15_1 117.2(6) . . ?
C11_1 C20_1 C15_1 118.9(6) . . ?
N30_1 C21_1 C11_1 112.7(5) . . ?
N30_1 C21_1 C22_1 108.1(5) . . ?
C11_1 C21_1 C22_1 114.3(6) . . ?
N30_1 C21_1 H21_1 107.1 . . ?
C11_1 C21_1 H21_1 107.1 . . ?
C22_1 C21_1 H21_1 107.1 . . ?
C23_1 C22_1 C21_1 115.6(8) . . ?
C23_1 C22_1 H22A_1 108.4 . . ?
C21_1 C22_1 H22A_1 108.4 . . ?
C23_1 C22_1 H22B_1 108.4 . . ?
C21_1 C22_1 H22B_1 108.4 . . ?
H22A_1 C22_1 H22B_1 107.4 . . ?
C22_1 C23_1 H23A_1 109.5 . . ?
C22_1 C23_1 H23B_1 109.5 . . ?
H23A_1 C23_1 H23B_1 109.5 . . ?
C22_1 C23_1 H23C_1 109.5 . . ?
H23A_1 C23_1 H23C_1 109.5 . . ?
H23B_1 C23_1 H23C_1 109.5 . . ?
O30_1 C30_1 N30_1 123.5(5) . . ?
O30_1 C30_1 C31_1 120.4(6) . . ?
N30_1 C30_1 C31_1 116.1(5) . . ?
C30_1 N30_1 C21_1 120.3(5) . . ?
C30_1 N30_1 H30_1 119.8 . . ?
C21_1 N30_1 H30_1 119.8 . . ?
C32_1 C31_1 C36_1 117.2(5) . . ?
C32_1 C31_1 C30_1 121.7(6) . . ?
C36_1 C31_1 C30_1 121.1(5) . . ?
C31_1 C32_1 C33_1 122.2(6) . . ?
C31_1 C32_1 Cl1_1 119.3(5) . . ?
C33_1 C32_1 Cl1_1 118.4(5) . . ?
C34_1 C33_1 C32_1 118.1(6) . . ?
C34_1 C33_1 H33_1 121.0 . . ?
C32_1 C33_1 H33_1 121.0 . . ?
C35_1 C34_1 C33_1 122.3(6) . . ?
C35_1 C34_1 Cl2_1 118.6(6) . . ?
C33_1 C34_1 Cl2_1 119.1(6) . . ?
C34_1 C35_1 C36_1 118.1(6) . . ?
C34_1 C35_1 H35_1 121.0 . . ?
C36_1 C35_1 H35_1 121.0 . . ?
C31_1 C36_1 C35_1 122.1(6) . . ?
C31_1 C36_1 Cl3_1 118.8(4) . . ?
C35_1 C36_1 Cl3_1 119.1(5) . . ?
C12_2 C11_2 C20_2 118.6(6) . . ?
C12_2 C11_2 C21_2 120.8(6) . . ?
C20_2 C11_2 C21_2 120.3(5) . . ?
C11_2 C12_2 C13_2 121.1(7) . . ?
C11_2 C12_2 H12_2 119.5 . . ?
C13_2 C12_2 H12_2 119.5 . . ?
C14_2 C13_2 C12_2 118.7(8) . . ?
C14_2 C13_2 H13_2 120.7 . . ?
C12_2 C13_2 H13_2 120.7 . . ?
C13_2 C14_2 C15_2 122.1(7) . . ?
C13_2 C14_2 H14_2 118.9 . . ?
C15_2 C14_2 H14_2 118.9 . . ?
C14_2 C15_2 C20_2 119.5(8) . . ?
C14_2 C15_2 C16_2 121.9(8) . . ?
C20_2 C15_2 C16_2 118.6(9) . . ?
C17_2 C16_2 C15_2 121.8(9) . . ?
C17_2 C16_2 H16_2 119.1 . . ?
C15_2 C16_2 H16_2 119.1 . . ?
C16_2 C17_2 C18_2 119.3(10) . . ?
C16_2 C17_2 H17_2 120.3 . . ?
C18_2 C17_2 H17_2 120.3 . . ?
C19_2 C18_2 C17_2 120.9(10) . . ?
C19_2 C18_2 H18_2 119.5 . . ?
C17_2 C18_2 H18_2 119.5 . . ?
C18_2 C19_2 C20_2 121.5(8) . . ?
C18_2 C19_2 H19_2 119.3 . . ?
C20_2 C19_2 H19_2 119.3 . . ?
C15_2 C20_2 C19_2 117.7(7) . . ?
C15_2 C20_2 C11_2 120.1(7) . . ?
C19_2 C20_2 C11_2 122.2(6) . . ?
N30_2 C21_2 C11_2 113.3(5) . . ?
N30_2 C21_2 C22_2 109.3(5) . . ?
C11_2 C21_2 C22_2 111.1(5) . . ?
N30_2 C21_2 H21_2 107.6 . . ?
C11_2 C21_2 H21_2 107.6 . . ?
C22_2 C21_2 H21_2 107.6 . . ?
C23_2 C22_2 C21_2 115.0(5) . . ?
C23_2 C22_2 H22A_2 108.5 . . ?
C21_2 C22_2 H22A_2 108.5 . . ?
C23_2 C22_2 H22B_2 108.5 . . ?
C21_2 C22_2 H22B_2 108.5 . . ?
H22A_2 C22_2 H22B_2 107.5 . . ?
C22_2 C23_2 H23A_2 109.5 . . ?
C22_2 C23_2 H23B_2 109.5 . . ?
H23A_2 C23_2 H23B_2 109.5 . . ?
C22_2 C23_2 H23C_2 109.5 . . ?
H23A_2 C23_2 H23C_2 109.5 . . ?
H23B_2 C23_2 H23C_2 109.5 . . ?
O30_2 C30_2 N30_2 123.6(5) . . ?
O30_2 C30_2 C31_2 121.0(5) . . ?
N30_2 C30_2 C31_2 115.3(5) . . ?
C30_2 N30_2 C21_2 120.3(5) . . ?
C30_2 N30_2 H30_2 119.8 . . ?
C21_2 N30_2 H30_2 119.8 . . ?
C36_2 C31_2 C32_2 116.6(5) . . ?
C36_2 C31_2 C30_2 121.1(6) . . ?
C32_2 C31_2 C30_2 122.3(6) . . ?
C33_2 C32_2 C31_2 123.2(6) . . ?
C33_2 C32_2 Cl1_2 118.8(5) . . ?
C31_2 C32_2 Cl1_2 118.0(5) . . ?
C32_2 C33_2 C34_2 118.1(6) . . ?
C32_2 C33_2 H33_2 121.0 . . ?
C34_2 C33_2 H33_2 121.0 . . ?
C35_2 C34_2 C33_2 119.9(6) . . ?
C35_2 C34_2 Cl2_2 120.9(5) . . ?
C33_2 C34_2 Cl2_2 119.2(5) . . ?
C34_2 C35_2 C36_2 121.1(6) . . ?
C34_2 C35_2 H35_2 119.5 . . ?
C36_2 C35_2 H35_2 119.5 . . ?
C35_2 C36_2 C31_2 121.1(6) . . ?
C35_2 C36_2 Cl3_2 118.4(5) . . ?
C31_2 C36_2 Cl3_2 120.4(4) . . ?

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
C20_1 C11_1 C12_1 C13_1 -0.2(10) . . . . ?
C21_1 C11_1 C12_1 C13_1 -177.0(6) . . . . ?
C11_1 C12_1 C13_1 C14_1 -1.2(12) . . . . ?
C12_1 C13_1 C14_1 C15_1 2.2(13) . . . . ?
C13_1 C14_1 C15_1 C16_1 178.7(8) . . . . ?
C13_1 C14_1 C15_1 C20_1 -1.8(12) . . . . ?
C14_1 C15_1 C16_1 C17_1 177.8(8) . . . . ?
C20_1 C15_1 C16_1 C17_1 -1.7(12) . . . . ?
C15_1 C16_1 C17_1 C18_1 0.2(14) . . . . ?
C16_1 C17_1 C18_1 C19_1 1.2(13) . . . . ?
C17_1 C18_1 C19_1 C20_1 -1.0(11) . . . . ?
C18_1 C19_1 C20_1 C11_1 -178.5(6) . . . . ?
C18_1 C19_1 C20_1 C15_1 -0.5(10) . . . . ?
C12_1 C11_1 C20_1 C19_1 178.6(6) . . . . ?
C21_1 C11_1 C20_1 C19_1 -4.6(9) . . . . ?
C12_1 C11_1 C20_1 C15_1 0.6(8) . . . . ?
C21_1 C11_1 C20_1 C15_1 177.4(5) . . . . ?
C14_1 C15_1 C20_1 C19_1 -177.7(6) . . . . ?
C16_1 C15_1 C20_1 C19_1 1.8(9) . . . . ?
C14_1 C15_1 C20_1 C11_1 0.4(9) . . . . ?
C16_1 C15_1 C20_1 C11_1 179.9(6) . . . . ?
C12_1 C11_1 C21_1 N30_1 -27.4(8) . . . . ?
C20_1 C11_1 C21_1 N30_1 155.9(5) . . . . ?
C12_1 C11_1 C21_1 C22_1 96.7(7) . . . . ?
C20_1 C11_1 C21_1 C22_1 -80.1(7) . . . . ?
N30_1 C21_1 C22_1 C23_1 69.1(9) . . . . ?
C11_1 C21_1 C22_1 C23_1 -57.3(9) . . . . ?
O30_1 C30_1 N30_1 C21_1 7.1(9) . . . . ?
C31_1 C30_1 N30_1 C21_1 -169.9(6) . . . . ?
C11_1 C21_1 N30_1 C30_1 -75.8(7) . . . . ?
C22_1 C21_1 N30_1 C30_1 156.8(6) . . . . ?
O30_1 C30_1 C31_1 C32_1 85.7(8) . . . . ?
N30_1 C30_1 C31_1 C32_1 -97.2(7) . . . . ?
O30_1 C30_1 C31_1 C36_1 -94.5(7) . . . . ?
N30_1 C30_1 C31_1 C36_1 82.6(8) . . . . ?
C36_1 C31_1 C32_1 C33_1 0.5(9) . . . . ?
C30_1 C31_1 C32_1 C33_1 -179.7(6) . . . . ?
C36_1 C31_1 C32_1 Cl1_1 179.5(4) . . . . ?
C30_1 C31_1 C32_1 Cl1_1 -0.7(8) . . . . ?
C31_1 C32_1 C33_1 C34_1 -0.6(10) . . . . ?
Cl1_1 C32_1 C33_1 C34_1 -179.6(6) . . . . ?
C32_1 C33_1 C34_1 C35_1 -0.6(11) . . . . ?
C32_1 C33_1 C34_1 Cl2_1 178.7(5) . . . . ?
C33_1 C34_1 C35_1 C36_1 1.8(11) . . . . ?
Cl2_1 C34_1 C35_1 C36_1 -177.5(5) . . . . ?
C32_1 C31_1 C36_1 C35_1 0.7(9) . . . . ?
C30_1 C31_1 C36_1 C35_1 -179.1(6) . . . . ?
C32_1 C31_1 C36_1 Cl3_1 -179.3(5) . . . . ?
C30_1 C31_1 C36_1 Cl3_1 0.9(8) . . . . ?
C34_1 C35_1 C36_1 C31_1 -1.9(10) . . . . ?
C34_1 C35_1 C36_1 Cl3_1 178.1(5) . . . . ?
C20_2 C11_2 C12_2 C13_2 1.7(10) . . . . ?
C21_2 C11_2 C12_2 C13_2 -171.7(7) . . . . ?
C11_2 C12_2 C13_2 C14_2 -0.4(12) . . . . ?
C12_2 C13_2 C14_2 C15_2 -1.6(12) . . . . ?
C13_2 C14_2 C15_2 C20_2 2.1(12) . . . . ?
C13_2 C14_2 C15_2 C16_2 -179.6(8) . . . . ?
C14_2 C15_2 C16_2 C17_2 -178.7(11) . . . . ?
C20_2 C15_2 C16_2 C17_2 -0.3(15) . . . . ?
C15_2 C16_2 C17_2 C18_2 -3(2) . . . . ?
C16_2 C17_2 C18_2 C19_2 5(2) . . . . ?
C17_2 C18_2 C19_2 C20_2 -4.6(17) . . . . ?
C14_2 C15_2 C20_2 C19_2 179.3(7) . . . . ?
C16_2 C15_2 C20_2 C19_2 0.9(10) . . . . ?
C14_2 C15_2 C20_2 C11_2 -0.7(10) . . . . ?
C16_2 C15_2 C20_2 C11_2 -179.1(7) . . . . ?
C18_2 C19_2 C20_2 C15_2 1.5(12) . . . . ?
C18_2 C19_2 C20_2 C11_2 -178.5(8) . . . . ?
C12_2 C11_2 C20_2 C15_2 -1.2(9) . . . . ?
C21_2 C11_2 C20_2 C15_2 172.3(6) . . . . ?
C12_2 C11_2 C20_2 C19_2 178.9(7) . . . . ?
C21_2 C11_2 C20_2 C19_2 -7.7(10) . . . . ?
C12_2 C11_2 C21_2 N30_2 -45.9(8) . . . . ?
C20_2 C11_2 C21_2 N30_2 140.8(5) . . . . ?
C12_2 C11_2 C21_2 C22_2 77.6(7) . . . . ?
C20_2 C11_2 C21_2 C22_2 -95.7(7) . . . . ?
N30_2 C21_2 C22_2 C23_2 -68.1(7) . . . . ?
C11_2 C21_2 C22_2 C23_2 166.2(6) . . . . ?
O30_2 C30_2 N30_2 C21_2 9.7(9) . . . . ?
C31_2 C30_2 N30_2 C21_2 -168.0(6) . . . . ?
C11_2 C21_2 N30_2 C30_2 -80.8(7) . . . . ?
C22_2 C21_2 N30_2 C30_2 154.7(5) . . . . ?
O30_2 C30_2 C31_2 C36_2 -103.4(8) . . . . ?
N30_2 C30_2 C31_2 C36_2 74.4(8) . . . . ?
O30_2 C30_2 C31_2 C32_2 74.1(9) . . . . ?
N30_2 C30_2 C31_2 C32_2 -108.1(7) . . . . ?
C36_2 C31_2 C32_2 C33_2 1.8(9) . . . . ?
C30_2 C31_2 C32_2 C33_2 -175.8(6) . . . . ?
C36_2 C31_2 C32_2 Cl1_2 179.7(5) . . . . ?
C30_2 C31_2 C32_2 Cl1_2 2.1(8) . . . . ?
C31_2 C32_2 C33_2 C34_2 -1.0(10) . . . . ?
Cl1_2 C32_2 C33_2 C34_2 -178.9(6) . . . . ?
C32_2 C33_2 C34_2 C35_2 0.4(11) . . . . ?
C32_2 C33_2 C34_2 Cl2_2 -179.9(5) . . . . ?
C33_2 C34_2 C35_2 C36_2 -0.7(11) . . . . ?
Cl2_2 C34_2 C35_2 C36_2 179.6(5) . . . . ?
C34_2 C35_2 C36_2 C31_2 1.6(10) . . . . ?
C34_2 C35_2 C36_2 Cl3_2 180.0(6) . . . . ?
C32_2 C31_2 C36_2 C35_2 -2.0(9) . . . . ?
C30_2 C31_2 C36_2 C35_2 175.6(6) . . . . ?
C32_2 C31_2 C36_2 Cl3_2 179.6(5) . . . . ?
C30_2 C31_2 C36_2 Cl3_2 -2.7(9) . . . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_jlo1
_database_code_depnum_ccdc_archive 'CCDC 2130651'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-12-23 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 N O S'
_chemical_formula_weight         289.42

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           4
_space_group_name_H-M_alt        'P 21'
_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                   7.5133(4)
_cell_length_b                   9.5794(4)
_cell_length_c                   12.1165(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.1664(12)
_cell_angle_gamma                90
_cell_volume                     841.69(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4900
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.04

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13381
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.741
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2974
_reflns_number_gt                2662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0250P)²+0.2083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2974
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.41000(11) 0.47783(7) 0.56697(6) 0.0338(2) Uani 1 1 d . . . . .
O1 O 0.5572(3) 0.3902(2) 0.53943(19) 0.0519(7) Uani 1 1 d . . . . .
N1 N 0.3385(3) 0.6009(2) 0.47286(19) 0.0303(6) Uani 1 1 d . . . . .
H1 H 0.384489 0.685679 0.484638 0.036 Uiso 1 1 calc R U . . .
C2 C 0.1964(4) 0.5673(3) 0.3686(2) 0.0280(7) Uani 1 1 d . . . . .
H2 H 0.135281 0.479105 0.383344 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0499(4) 0.6818(3) 0.3458(3) 0.0413(8) Uani 1 1 d . . . . .
H3A H 0.110589 0.773638 0.346042 0.050 Uiso 1 1 calc R U . . .
H3B H -0.034938 0.667734 0.268998 0.050 Uiso 1 1 calc R U . . .
C4 C -0.0609(5) 0.6828(5) 0.4348(3) 0.0722(13) Uani 1 1 d . . . . .
H4A H -0.157305 0.754330 0.414670 0.108 Uiso 1 1 calc R U . . .
H4B H 0.021158 0.703631 0.510181 0.108 Uiso 1 1 calc R U . . .
H4C H -0.117950 0.591129 0.436601 0.108 Uiso 1 1 calc R U . . .
C11 C 0.2706(4) 0.5418(3) 0.2649(2) 0.0273(6) Uani 1 1 d . . . . .
C12 C 0.4374(4) 0.5947(3) 0.2598(3) 0.0357(7) Uani 1 1 d . . . . .
H12 H 0.509467 0.645862 0.323021 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5046(5) 0.5747(4) 0.1623(3) 0.0473(9) Uani 1 1 d . . . . .
H13 H 0.619922 0.613667 0.160093 0.057 Uiso 1 1 calc R U . . .
C14 C 0.4055(5) 0.5004(4) 0.0723(3) 0.0445(9) Uani 1 1 d . . . . .
H14 H 0.452225 0.487709 0.007282 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2337(4) 0.4413(3) 0.0731(2) 0.0380(8) Uani 1 1 d . . . . .
C16 C 0.1308(5) 0.3598(4) -0.0189(3) 0.0497(9) Uani 1 1 d . . . . .
H16 H 0.177858 0.344335 -0.083442 0.060 Uiso 1 1 calc R U . . .
C17 C -0.0344(6) 0.3032(4) -0.0169(3) 0.0535(10) Uani 1 1 d . . . . .
H17 H -0.101074 0.248012 -0.079192 0.064 Uiso 1 1 calc R U . . .
C18 C -0.1053(5) 0.3264(3) 0.0767(3) 0.0451(9) Uani 1 1 d . . . . .
H18 H -0.221062 0.287149 0.077546 0.054 Uiso 1 1 calc R U . . .
C19 C -0.0112(4) 0.4048(3) 0.1672(3) 0.0341(7) Uani 1 1 d . . . . .
H19 H -0.063401 0.420062 0.229588 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1629(4) 0.4638(3) 0.1699(2) 0.0283(6) Uani 1 1 d . . . . .
C21 C 0.5321(5) 0.5860(3) 0.6893(2) 0.0379(8) Uani 1 1 d . . . . .
C22 C 0.7021(5) 0.6492(4) 0.6649(3) 0.0460(9) Uani 1 1 d . . . . .
H22A H 0.779142 0.691186 0.735015 0.069 Uiso 1 1 calc R U . . .
H22B H 0.665337 0.721230 0.605911 0.069 Uiso 1 1 calc R U . . .
H22C H 0.772084 0.576232 0.638124 0.069 Uiso 1 1 calc R U . . .
C23 C 0.5888(6) 0.4806(5) 0.7871(2) 0.0657(11) Uani 1 1 d . . . . .
H23A H 0.660974 0.528018 0.855971 0.099 Uiso 1 1 calc R U . . .
H23B H 0.663586 0.406738 0.765573 0.099 Uiso 1 1 calc R U . . .
H23C H 0.478201 0.439449 0.802325 0.099 Uiso 1 1 calc R U . . .
C24 C 0.4018(6) 0.6957(4) 0.7131(3) 0.0646(11) Uani 1 1 d . . . . .
H24A H 0.462158 0.746463 0.783089 0.097 Uiso 1 1 calc R U . . .
H24B H 0.289883 0.650454 0.722697 0.097 Uiso 1 1 calc R U . . .
H24C H 0.369110 0.761235 0.648800 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.494(2) . ?
S1 N1 1.630(2) . ?
S1 C21 1.844(3) . ?
N1 C2 1.461(3) . ?
N1 H1 0.8800 . ?
C2 C11 1.522(4) . ?
C2 C3 1.527(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.525(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 C12 1.368(4) . ?
C11 C20 1.431(4) . ?
C12 C13 1.414(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.352(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.412(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(4) . ?
C15 C20 1.426(4) . ?
C16 C17 1.360(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.364(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.417(4) . ?
C19 H19 0.9500 . ?
C21 C22 1.510(5) . ?
C21 C24 1.514(5) . ?
C21 C23 1.530(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 112.20(13) . . ?
O1 S1 C21 104.68(14) . . ?
N1 S1 C21 99.17(13) . . ?
C2 N1 S1 118.60(19) . . ?
C2 N1 H1 120.7 . . ?
S1 N1 H1 120.7 . . ?
N1 C2 C11 114.0(2) . . ?
N1 C2 C3 109.1(2) . . ?
C11 C2 C3 111.6(2) . . ?
N1 C2 H2 107.3 . . ?
C11 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C4 C3 C2 112.2(3) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C12 C11 C20 119.3(3) . . ?
C12 C11 C2 121.0(3) . . ?
C20 C11 C2 119.7(2) . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 121.9(3) . . ?
C14 C15 C20 118.9(3) . . ?
C16 C15 C20 119.2(3) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 117.4(3) . . ?
C19 C20 C11 123.5(3) . . ?
C15 C20 C11 119.1(3) . . ?
C22 C21 C24 112.4(3) . . ?
C22 C21 C23 109.7(3) . . ?
C24 C21 C23 111.9(3) . . ?
C22 C21 S1 109.7(2) . . ?
C24 C21 S1 109.4(2) . . ?
C23 C21 S1 103.3(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 S1 N1 C2 84.3(2) . . . . ?
C21 S1 N1 C2 -165.7(2) . . . . ?
S1 N1 C2 C11 -100.2(2) . . . . ?
S1 N1 C2 C3 134.3(2) . . . . ?
N1 C2 C3 C4 -68.1(4) . . . . ?
C11 C2 C3 C4 165.0(3) . . . . ?
N1 C2 C11 C12 -22.5(4) . . . . ?
C3 C2 C11 C12 101.7(3) . . . . ?
N1 C2 C11 C20 158.8(2) . . . . ?
C3 C2 C11 C20 -77.0(3) . . . . ?
C20 C11 C12 C13 0.5(5) . . . . ?
C2 C11 C12 C13 -178.2(3) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C13 C14 C15 C20 1.5(5) . . . . ?
C14 C15 C16 C17 179.8(3) . . . . ?
C20 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C18 C19 C20 C15 1.6(4) . . . . ?
C18 C19 C20 C11 -177.3(3) . . . . ?
C14 C15 C20 C19 179.1(3) . . . . ?
C16 C15 C20 C19 -1.3(4) . . . . ?
C14 C15 C20 C11 -2.0(4) . . . . ?
C16 C15 C20 C11 177.6(3) . . . . ?
C12 C11 C20 C19 179.9(3) . . . . ?
C2 C11 C20 C19 -1.4(4) . . . . ?
C12 C11 C20 C15 1.0(4) . . . . ?
C2 C11 C20 C15 179.7(3) . . . . ?
O1 S1 C21 C22 47.4(3) . . . . ?
N1 S1 C21 C22 -68.6(2) . . . . ?
O1 S1 C21 C24 171.1(3) . . . . ?
N1 S1 C21 C24 55.1(3) . . . . ?
O1 S1 C21 C23 -69.6(3) . . . . ?
N1 S1 C21 C23 174.5(2) . . . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032

