# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_breitjs_5_74_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1840179'
_audit_update_record             
;
2018-04-27 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_audit_creation_date             2018-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
daniel.kratzert@ac.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N O3 S'
_chemical_formula_sum            'C17 H21 N O3 S'
_chemical_formula_weight         319.41
_chemical_absolute_configuration ad
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.89110(10)
_cell_length_b                   12.2990(3)
_cell_length_c                   22.4992(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1630.17(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.992
_cell_measurement_theta_min      3.182
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0887 before and 0.0413 after correction. The Ratio of minimum to maximum transmission is 0.9556. 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    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethyl acetate by slow evaporation'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22098
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         1.810
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4485
_reflns_number_total             4988
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 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         0.264
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.030
_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)+(0.0461P)²+0.1951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0890
_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 Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C13(H13), C15(H15), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.93248(7) 0.49989(4) 0.55392(2) 0.01618(10) Uani 1 1 d . . . . .
N1 N 0.8139(3) 0.42063(12) 0.60690(7) 0.0154(3) Uani 1 1 d . . . . .
O1 O 1.1734(2) 0.48730(11) 0.55513(6) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.8932(3) 0.42901(15) 0.66513(8) 0.0158(4) Uani 1 1 d . . . . .
O2 O 0.8117(2) 0.47377(11) 0.50065(6) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.7822(3) 0.35989(16) 0.71271(8) 0.0190(4) Uani 1 1 d . . . . .
H2A H 0.710185 0.409558 0.741743 0.023 Uiso 1 1 calc R . . . .
H2B H 0.903958 0.320351 0.733995 0.023 Uiso 1 1 calc R . . . .
C3 C 0.6046(3) 0.27692(16) 0.69361(8) 0.0174(4) Uani 1 1 d . . . . .
H3 H 0.685436 0.210609 0.678992 0.021 Uiso 1 1 calc R . . . .
O3 O 1.0434(2) 0.49269(11) 0.67781(6) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.4726(3) 0.32551(16) 0.64186(8) 0.0193(4) Uani 1 1 d . . . . .
H4A H 0.349674 0.275048 0.630061 0.023 Uiso 1 1 calc R . . . .
H4B H 0.401998 0.394800 0.654515 0.023 Uiso 1 1 calc R . . . .
C5 C 0.6272(3) 0.34622(15) 0.58888(8) 0.0156(4) Uani 1 1 d . . . . .
H5 H 0.536089 0.383117 0.557277 0.019 Uiso 1 1 calc R . . . .
C6 C 0.7145(4) 0.24027(15) 0.56405(8) 0.0196(4) Uani 1 1 d . . . . .
H6 H 0.604210 0.189812 0.550300 0.024 Uiso 1 1 calc R . . . .
C8 C 0.4493(3) 0.24347(15) 0.74367(9) 0.0207(4) Uani 1 1 d . . . . .
H8 H 0.374724 0.304280 0.765790 0.025 Uiso 1 1 calc R . . . .
C7 C 0.9289(4) 0.21097(17) 0.55958(9) 0.0241(4) Uani 1 1 d . . . . .
H7A H 1.045414 0.258664 0.572730 0.029 Uiso 1 1 calc R . . . .
H7B H 0.967082 0.142150 0.543214 0.029 Uiso 1 1 calc R . . . .
C9 C 0.5038(4) 0.14365(18) 0.77982(9) 0.0259(5) Uani 1 1 d . . . . .
H9A H 0.466419 0.144865 0.822713 0.031 Uiso 1 1 calc R . . . .
H9B H 0.642373 0.102303 0.769411 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3092(3) 0.14238(17) 0.73609(9) 0.0237(4) Uani 1 1 d . . . . .
H10A H 0.328874 0.100139 0.698989 0.028 Uiso 1 1 calc R . . . .
H10B H 0.152960 0.142691 0.752279 0.028 Uiso 1 1 calc R . . . .
C11 C 0.8617(3) 0.63359(15) 0.57420(8) 0.0172(4) Uani 1 1 d . . . . .
C12 C 1.0131(3) 0.69572(16) 0.60663(9) 0.0219(4) Uani 1 1 d . . . . .
H12 H 1.155323 0.666532 0.618492 0.026 Uiso 1 1 calc R . . . .
C13 C 0.9537(4) 0.80138(16) 0.62158(9) 0.0253(4) Uani 1 1 d . . . . .
H13 H 1.056740 0.844490 0.643930 0.030 Uiso 1 1 calc R . . . .
C14 C 0.7459(4) 0.84553(16) 0.60443(9) 0.0256(4) Uani 1 1 d . . . . .
C15 C 0.5979(4) 0.78192(16) 0.57102(9) 0.0242(4) Uani 1 1 d . . . . .
H15 H 0.456908 0.811540 0.558493 0.029 Uiso 1 1 calc R . . . .
C16 C 0.6535(3) 0.67555(16) 0.55569(9) 0.0197(4) Uani 1 1 d . . . . .
H16 H 0.551509 0.632369 0.533050 0.024 Uiso 1 1 calc R . . . .
C17 C 0.6805(6) 0.95887(19) 0.62286(12) 0.0421(7) Uani 1 1 d . . . . .
H17A H 0.817823 1.001241 0.631074 0.063 Uiso 1 1 calc GR . . . .
H17B H 0.586452 0.955560 0.658744 0.063 Uiso 1 1 calc GR . . . .
H17C H 0.594579 0.993630 0.590761 0.063 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 N1 1.6910(16) . ?
S1 O1 1.4277(14) . ?
S1 O2 1.4302(14) . ?
S1 C11 1.757(2) . ?
N1 C1 1.395(2) . ?
N1 C5 1.487(2) . ?
C1 C2 1.515(3) . ?
C1 O3 1.216(2) . ?
C2 C3 1.523(3) . ?
C3 C4 1.522(3) . ?
C3 C8 1.508(3) . ?
C4 C5 1.522(3) . ?
C5 C6 1.508(3) . ?
C6 C7 1.318(3) . ?
C8 C9 1.507(3) . ?
C8 C10 1.502(3) . ?
C9 C10 1.511(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.391(3) . ?
C14 C17 1.504(3) . ?
C15 C16 1.392(3) . ?

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
N1 S1 C11 104.98(8) . . ?
O1 S1 N1 109.55(8) . . ?
O1 S1 O2 119.08(9) . . ?
O1 S1 C11 109.41(9) . . ?
O2 S1 N1 104.82(8) . . ?
O2 S1 C11 108.05(9) . . ?
C1 N1 S1 118.76(13) . . ?
C1 N1 C5 123.32(15) . . ?
C5 N1 S1 117.92(12) . . ?
N1 C1 C2 118.54(16) . . ?
O3 C1 N1 120.80(17) . . ?
O3 C1 C2 120.63(17) . . ?
C1 C2 C3 118.21(16) . . ?
C4 C3 C2 107.68(16) . . ?
C8 C3 C2 112.87(16) . . ?
C8 C3 C4 111.61(15) . . ?
C5 C4 C3 111.03(15) . . ?
N1 C5 C4 109.40(15) . . ?
N1 C5 C6 112.39(15) . . ?
C6 C5 C4 110.47(16) . . ?
C7 C6 C5 126.24(19) . . ?
C9 C8 C3 119.73(17) . . ?
C10 C8 C3 118.31(17) . . ?
C10 C8 C9 60.26(14) . . ?
C8 C9 C10 59.70(13) . . ?
C8 C10 C9 60.04(13) . . ?
C12 C11 S1 120.11(15) . . ?
C12 C11 C16 121.35(18) . . ?
C16 C11 S1 118.52(15) . . ?
C11 C12 C13 118.9(2) . . ?
C12 C13 C14 121.3(2) . . ?
C13 C14 C17 120.6(2) . . ?
C15 C14 C13 118.72(19) . . ?
C15 C14 C17 120.6(2) . . ?
C14 C15 C16 121.0(2) . . ?
C15 C16 C11 118.72(19) . . ?

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 178.47(13) . . . . ?
S1 N1 C1 O3 0.6(2) . . . . ?
S1 N1 C5 C4 -152.69(13) . . . . ?
S1 N1 C5 C6 84.22(17) . . . . ?
S1 C11 C12 C13 179.41(16) . . . . ?
S1 C11 C16 C15 -179.20(15) . . . . ?
N1 S1 C11 C12 95.73(17) . . . . ?
N1 S1 C11 C16 -85.74(16) . . . . ?
N1 C1 C2 C3 5.6(3) . . . . ?
N1 C5 C6 C7 2.2(3) . . . . ?
O1 S1 N1 C1 52.40(16) . . . . ?
O1 S1 N1 C5 -128.36(14) . . . . ?
O1 S1 C11 C12 -21.76(18) . . . . ?
O1 S1 C11 C16 156.77(15) . . . . ?
C1 N1 C5 C4 26.5(2) . . . . ?
C1 N1 C5 C6 -96.6(2) . . . . ?
C1 C2 C3 C4 -35.5(2) . . . . ?
C1 C2 C3 C8 -159.11(16) . . . . ?
O2 S1 N1 C1 -178.73(13) . . . . ?
O2 S1 N1 C5 0.51(15) . . . . ?
O2 S1 C11 C12 -152.82(15) . . . . ?
O2 S1 C11 C16 25.71(18) . . . . ?
C2 C3 C4 C5 62.5(2) . . . . ?
C2 C3 C8 C9 -93.9(2) . . . . ?
C2 C3 C8 C10 -163.95(17) . . . . ?
C3 C4 C5 N1 -58.2(2) . . . . ?
C3 C4 C5 C6 66.0(2) . . . . ?
C3 C8 C9 C10 -107.6(2) . . . . ?
C3 C8 C10 C9 109.94(19) . . . . ?
O3 C1 C2 C3 -176.51(17) . . . . ?
C4 C3 C8 C9 144.66(18) . . . . ?
C4 C3 C8 C10 74.6(2) . . . . ?
C4 C5 C6 C7 -120.3(2) . . . . ?
C5 N1 C1 C2 -0.7(3) . . . . ?
C5 N1 C1 O3 -178.57(16) . . . . ?
C8 C3 C4 C5 -173.15(16) . . . . ?
C11 S1 N1 C1 -64.99(15) . . . . ?
C11 S1 N1 C5 114.25(14) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C11 C16 C15 -0.7(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 C17 177.8(2) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
C17 C14 C15 C16 -177.6(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id JS_5_74
_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_breitjs_6_53_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1845388'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
daniel.kratzert@ac.uni-freiburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.136(8)
_cell_length_b                   17.429(15)
_cell_length_c                   13.045(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.20(3)
_cell_angle_gamma                90
_cell_volume                     1785(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.825
_cell_measurement_theta_min      2.860
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1108 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.9335. 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    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20123
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.643
_diffrn_reflns_theta_min         1.996
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4117
_reflns_number_total             4497
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 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         0.376
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4497
_refine_ls_number_restraints     529
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.9017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0884
_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. Restrained distances
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C8-C13 \\sim C8A-C13A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C6-C8 \\sim C6-C8A
 with sigma of 0.04
 C8-C10 \\sim C8A-C10A
 with sigma of 0.04
 C8-C12 \\sim C8A-C12A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 C9-C13 \\sim C9A-C13A
 with sigma of 0.04
 C10-C12 \\sim C10A-C12A
 with sigma of 0.04
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C6-C7 \\sim C6A-C7
 with sigma of 0.02
 C6-C5A \\sim C6A-C5A
 with sigma of 0.02
 C4-C8 \\sim C4-C8A
 with sigma of 0.04
 C4-C5A \\sim C4A-C5A
 with sigma of 0.02
 C1-C4 \\sim C1-C4A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6
 with sigma of 0.02
 C5-C8 \\sim C5A-C8A
 with sigma of 0.02
 C5-C9 \\sim C5A-C9A
 with sigma of 0.04
 C5-C13 \\sim C5A-C13A
 with sigma of 0.04
 C5-C6 \\sim C5-C6A
 with sigma of 0.02
 C4-C5 \\sim C4-C5A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C7-C6A \\sim C7-C6
 with sigma of 0.02
 C5A-C4A \\sim C5-C4
 with sigma of 0.02
 C4-C1 \\sim C4A-C1
 with sigma of 0.02
3. Restrained planarity
 C8A, C13A, C12A, C11A, C10A, C9A
 with sigma of 0.06
 C8, C13, C12, C11, C10, C9
 with sigma of 0.06
4. Rigid bond restraints
 C4, C5, C6, C8, C9, C10, C11, C12, C13, C5A, C8A, C9A, C10A, C11A, C12A, C13A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C4 \\sim H4A \\sim H4B \\sim C5 \\sim H5 \\sim C6 \\sim H6A \\sim H6B \\sim C8
\\sim C9 \\sim H9 \\sim C10 \\sim H10 \\sim C11 \\sim H11 \\sim C12 \\sim H12
\\sim C13 \\sim H13 \\sim C5A \\sim H5A \\sim C8A \\sim C9A \\sim H9A \\sim
C10A \\sim H10A \\sim C11A \\sim H11A \\sim C12A \\sim H12A \\sim C13A \\sim
H13A \\sim C4A \\sim H4AA \\sim H4AB \\sim C6A \\sim H6AA \\sim H6AB: within
1.1A with sigma of 0.01 and sigma for terminal atoms of 0.02
C4 \\sim C5 \\sim C6 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13
\\sim C5A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim
C4A \\sim C6A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Others
 Sof(C5A)=Sof(H5A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=1-FVAR(1)
 Sof(C5)=Sof(H5)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=FVAR(1)
 Sof(H1B)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=1-FVAR(2)
 Sof(H1A)=Sof(C4)=Sof(H4A)=Sof(H4B)=FVAR(2)
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(3)
 Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B), C5(H5), C5A(H5A)
7.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C4A(H4AA,H4AB), C6A(H6AA,H6AB)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A)
7.d X=CH2 refined with riding coordinates:
 C3(H3A,H3B)
7.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.34175(4) 0.51966(2) 0.81296(2) 0.01773(8) Uani 1 1 d . . . . .
N1 N 0.50872(13) 0.58020(6) 0.85959(8) 0.0186(2) Uani 1 1 d . . . . .
O1 O 0.66937(12) 0.51825(5) 0.76389(7) 0.0252(2) Uani 1 1 d . . . . .
C1 C 0.47572(15) 0.65170(7) 0.91672(10) 0.0194(2) Uani 1 1 d D . . . .
H1A H 0.415344 0.637433 0.971594 0.023 Uiso 0.810(13) 1 calc R . P A 1
H1B H 0.400287 0.634147 0.961523 0.023 Uiso 0.190(13) 1 calc R . P A 2
O2 O 0.40509(12) 0.44227(5) 0.82524(7) 0.0247(2) Uani 1 1 d . . . . .
C2 C 0.36773(17) 0.70789(7) 0.83906(10) 0.0237(3) Uani 1 1 d . . . . .
H2 H 0.401305 0.719640 0.776369 0.028 Uiso 1 1 calc R . . . .
C3 C 0.22921(17) 0.74177(8) 0.85295(11) 0.0286(3) Uani 1 1 d . . . . .
H3A H 0.192214 0.731254 0.914794 0.034 Uiso 1 1 calc R . . . .
H3B H 0.166987 0.776556 0.801046 0.034 Uiso 1 1 calc R . . . .
O3 O 0.21686(11) 0.54256(5) 0.86746(7) 0.02161(19) Uani 1 1 d . . . . .
C4 C 0.6419(3) 0.69523(18) 0.9705(3) 0.0241(6) Uani 0.810(13) 1 d D U P A 1
H4A H 0.659444 0.736545 0.922344 0.029 Uiso 0.810(13) 1 calc R U P A 1
H4B H 0.628661 0.719678 1.036351 0.029 Uiso 0.810(13) 1 calc R U P A 1
C5 C 0.80011(16) 0.64380(8) 0.99817(12) 0.0155(3) Uani 0.889(4) 1 d D U P A 1
H5 H 0.780805 0.600207 1.043481 0.019 Uiso 0.889(4) 1 calc R U P A 1
C6 C 0.8149(4) 0.6125(3) 0.8906(3) 0.0235(6) Uani 0.827(15) 1 d D U P A 1
H6A H 0.829523 0.656113 0.845197 0.028 Uiso 0.827(15) 1 calc R U P A 1
H6B H 0.918155 0.580049 0.902687 0.028 Uiso 0.827(15) 1 calc R U P A 1
C7 C 0.66145(15) 0.56552(7) 0.83185(10) 0.0207(2) Uani 1 1 d D . . . .
C8 C 0.9638(2) 0.68565(10) 1.05440(14) 0.0156(3) Uani 0.889(4) 1 d D U P A 1
C9 C 0.9751(3) 0.76607(12) 1.06251(17) 0.0198(4) Uani 0.889(4) 1 d D U P A 1
H9 H 0.876232 0.796198 1.034473 0.024 Uiso 0.889(4) 1 calc R U P A 1
C10 C 1.1288(3) 0.80255(18) 1.1110(3) 0.0241(5) Uani 0.889(4) 1 d D U P A 1
H10 H 1.134080 0.856943 1.115466 0.029 Uiso 0.889(4) 1 calc R U P A 1
C11 C 1.2748(4) 0.75868(15) 1.1528(3) 0.0224(5) Uani 0.889(4) 1 d D U P A 1
H11 H 1.379646 0.783194 1.185642 0.027 Uiso 0.889(4) 1 calc R U P A 1
C12 C 1.2662(3) 0.67848(16) 1.1462(2) 0.0210(5) Uani 0.889(4) 1 d D U P A 1
H12 H 1.365259 0.648597 1.174869 0.025 Uiso 0.889(4) 1 calc R U P A 1
C13 C 1.1119(3) 0.64229(13) 1.09732(16) 0.0190(4) Uani 0.889(4) 1 d D U P A 1
H13 H 1.107003 0.587885 1.093102 0.023 Uiso 0.889(4) 1 calc R U P A 1
C14 C 0.26188(15) 0.54038(7) 0.67590(9) 0.0175(2) Uani 1 1 d . . . . .
C15 C 0.33172(15) 0.50460(7) 0.60042(10) 0.0203(2) Uani 1 1 d . . . . .
H15 H 0.422122 0.468729 0.621952 0.024 Uiso 1 1 calc R . . . .
C16 C 0.26573(16) 0.52276(7) 0.49298(10) 0.0210(2) Uani 1 1 d . . . . .
H16 H 0.313465 0.499359 0.441617 0.025 Uiso 1 1 calc R . . . .
C17 C 0.13068(15) 0.57474(7) 0.45942(10) 0.0190(2) Uani 1 1 d . . . . .
C18 C 0.05972(15) 0.60798(7) 0.53653(10) 0.0188(2) Uani 1 1 d . . . . .
H18 H -0.033852 0.642205 0.514823 0.023 Uiso 1 1 calc R . . . .
C19 C 0.12483(15) 0.59140(7) 0.64457(10) 0.0182(2) Uani 1 1 d . . . . .
H19 H 0.076703 0.614456 0.695995 0.022 Uiso 1 1 calc R . . . .
C20 C 0.06460(18) 0.59507(8) 0.34280(10) 0.0243(3) Uani 1 1 d . . . . .
H20A H 0.076489 0.550621 0.299297 0.036 Uiso 1 1 calc GR . . . .
H20B H 0.130352 0.638166 0.325950 0.036 Uiso 1 1 calc GR . . . .
H20C H -0.055746 0.609563 0.327805 0.036 Uiso 1 1 calc GR . . . .
C5A C 0.8005(13) 0.6697(7) 0.9513(11) 0.0222(18) Uani 0.111(4) 1 d D U P A 2
H5A H 0.772760 0.704909 0.888673 0.027 Uiso 0.111(4) 1 calc R U P A 2
C8A C 0.9629(17) 0.7032(8) 1.0272(12) 0.018(2) Uani 0.111(4) 1 d D U P A 2
C9A C 0.996(2) 0.7799(9) 1.0471(15) 0.020(2) Uani 0.111(4) 1 d D U P A 2
H9A H 0.915464 0.818267 1.016428 0.023 Uiso 0.111(4) 1 calc R U P A 2
C10A C 1.155(3) 0.7988(15) 1.115(3) 0.022(2) Uani 0.111(4) 1 d D U P A 2
H10A H 1.179399 0.851454 1.131026 0.027 Uiso 0.111(4) 1 calc R U P A 2
C11A C 1.279(3) 0.7455(14) 1.159(3) 0.022(2) Uani 0.111(4) 1 d D U P A 2
H11A H 1.388027 0.761301 1.200660 0.026 Uiso 0.111(4) 1 calc R U P A 2
C12A C 1.240(3) 0.6684(14) 1.142(2) 0.022(2) Uani 0.111(4) 1 d D U P A 2
H12A H 1.317293 0.629381 1.175163 0.026 Uiso 0.111(4) 1 calc R U P A 2
C13A C 1.085(2) 0.6514(11) 1.0759(14) 0.023(2) Uani 0.111(4) 1 d D U P A 2
H13A H 1.058658 0.598589 1.062179 0.027 Uiso 0.111(4) 1 calc R U P A 2
C4A C 0.6487(13) 0.6753(10) 0.9996(10) 0.0255(18) Uani 0.190(13) 1 d D U P A 2
H4AA H 0.639107 0.728634 1.023643 0.031 Uiso 0.190(13) 1 calc R U P A 2
H4AB H 0.668244 0.641344 1.062444 0.031 Uiso 0.190(13) 1 calc R U P A 2
C6A C 0.8232(18) 0.5925(8) 0.9073(13) 0.0189(19) Uani 0.173(15) 1 d D U P A 2
H6AA H 0.858783 0.555240 0.966306 0.023 Uiso 0.173(15) 1 calc R U P A 2
H6AB H 0.914307 0.595106 0.869888 0.023 Uiso 0.173(15) 1 calc R U P A 2


_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 N1 1.7017(15) . ?
S1 O2 1.4378(14) . ?
S1 O3 1.4409(13) . ?
S1 C14 1.772(2) . ?
N1 C1 1.5117(17) . ?
N1 C7 1.4058(19) . ?
O1 C7 1.2243(17) . ?
C1 C2 1.513(2) . ?
C1 C4 1.549(3) . ?
C1 C4A 1.588(10) . ?
C2 C3 1.326(2) . ?
C4 C5 1.532(3) . ?
C5 C6 1.540(3) . ?
C5 C8 1.527(2) . ?
C6 C7 1.521(3) . ?
C7 C6A 1.498(13) . ?
C8 C9 1.407(3) . ?
C8 C13 1.408(2) . ?
C9 C10 1.398(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.401(3) . ?
C14 C15 1.4052(19) . ?
C14 C19 1.4008(19) . ?
C15 C16 1.399(2) . ?
C16 C17 1.403(2) . ?
C17 C18 1.4090(19) . ?
C17 C20 1.517(2) . ?
C18 C19 1.400(2) . ?
C5A C8A 1.543(13) . ?
C5A C4A 1.530(13) . ?
C5A C6A 1.493(14) . ?
C8A C9A 1.375(15) . ?
C8A C13A 1.368(15) . ?
C9A C10A 1.400(17) . ?
C10A C11A 1.381(17) . ?
C11A C12A 1.385(17) . ?
C12A C13A 1.364(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C14 106.35(6) . . ?
O2 S1 N1 108.22(8) . . ?
O2 S1 O3 118.91(6) . . ?
O2 S1 C14 109.24(6) . . ?
O3 S1 N1 104.60(8) . . ?
O3 S1 C14 108.77(8) . . ?
C1 N1 S1 117.32(9) . . ?
C7 N1 S1 118.16(10) . . ?
C7 N1 C1 124.06(10) . . ?
N1 C1 C2 110.52(12) . . ?
N1 C1 C4 112.35(12) . . ?
N1 C1 C4A 108.0(5) . . ?
C2 C1 C4 105.71(19) . . ?
C2 C1 C4A 122.9(7) . . ?
C3 C2 C1 124.17(13) . . ?
C5 C4 C1 113.58(19) . . ?
C4 C5 C6 104.7(3) . . ?
C8 C5 C4 114.01(15) . . ?
C8 C5 C6 109.90(15) . . ?
C7 C6 C5 113.6(2) . . ?
N1 C7 C6 115.90(17) . . ?
N1 C7 C6A 117.2(6) . . ?
O1 C7 N1 121.78(12) . . ?
O1 C7 C6 122.32(17) . . ?
O1 C7 C6A 118.9(6) . . ?
C9 C8 C5 122.94(16) . . ?
C9 C8 C13 118.20(17) . . ?
C13 C8 C5 118.83(17) . . ?
C10 C9 C8 121.4(2) . . ?
C11 C10 C9 119.7(3) . . ?
C10 C11 C12 119.9(2) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C8 120.7(2) . . ?
C15 C14 S1 120.52(11) . . ?
C19 C14 S1 118.49(9) . . ?
C19 C14 C15 120.96(12) . . ?
C16 C15 C14 118.82(13) . . ?
C15 C16 C17 121.47(11) . . ?
C16 C17 C18 118.49(12) . . ?
C16 C17 C20 120.44(11) . . ?
C18 C17 C20 121.07(13) . . ?
C19 C18 C17 121.08(13) . . ?
C18 C19 C14 119.14(11) . . ?
C4A C5A C8A 111.1(10) . . ?
C6A C5A C8A 114.6(10) . . ?
C6A C5A C4A 114.3(12) . . ?
C9A C8A C5A 125.7(13) . . ?
C13A C8A C5A 116.2(12) . . ?
C13A C8A C9A 118.1(14) . . ?
C8A C9A C10A 116.9(16) . . ?
C11A C10A C9A 124(2) . . ?
C10A C11A C12A 118(2) . . ?
C13A C12A C11A 116.7(18) . . ?
C12A C13A C8A 126.0(17) . . ?
C5A C4A C1 111.7(8) . . ?
C5A C6A C7 111.1(9) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
