# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mx5919
_database_code_depnum_ccdc_archive 'CCDC 1849601'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2018-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N3 O3 S'
_chemical_formula_sum            'C22 H17 N3 O3 S'
_chemical_formula_weight         403.44
_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                   7.6209(15)
_cell_length_b                   12.073(2)
_cell_length_c                   21.125(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.86(3)
_cell_angle_gamma                90
_cell_volume                     1929.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4833
_cell_measurement_theta_min      1.6867
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14264
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.942
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3917
_reflns_number_total             4390
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.225
_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)+(0.0228P)²+1.8228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
;
_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 0.73514(9) 0.50783(6) 0.44724(3) 0.02747(17) Uani 1 1 d . . . . .
O1 O 0.7202(2) 0.44503(16) 0.51272(8) 0.0313(4) Uani 1 1 d . . . . .
O2 O 0.6892(3) 0.61888(16) 0.45955(10) 0.0402(5) Uani 1 1 d . . . . .
O3 O 0.9006(2) 0.48416(17) 0.42638(9) 0.0366(5) Uani 1 1 d . . . . .
N1 N 0.5803(3) 0.45294(18) 0.39714(10) 0.0251(5) Uani 1 1 d . . . . .
N2 N 0.1001(3) 0.51038(18) 0.17607(11) 0.0315(5) Uani 1 1 d . . . . .
N3 N 0.1511(3) 0.15949(19) 0.21168(11) 0.0349(6) Uani 1 1 d . . . . .
C1 C 0.5367(3) 0.3503(2) 0.40290(11) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.6124(3) 0.2798(2) 0.45603(11) 0.0244(5) Uani 1 1 d . . . . .
C3 C 0.7070(3) 0.3297(2) 0.50936(12) 0.0292(6) Uani 1 1 d . . . . .
C4 C 0.7829(4) 0.2703(3) 0.56114(13) 0.0393(7) Uani 1 1 d . . . . .
H4 H 0.844247 0.305842 0.596086 0.047 Uiso 1 1 calc R . . . .
C5 C 0.7656(4) 0.1565(3) 0.55977(14) 0.0446(8) Uani 1 1 d . . . . .
H5 H 0.816561 0.114913 0.594203 0.053 Uiso 1 1 calc R . . . .
C6 C 0.6733(4) 0.1031(3) 0.50793(14) 0.0406(7) Uani 1 1 d . . . . .
H6 H 0.663095 0.026327 0.507672 0.049 Uiso 1 1 calc R . . . .
C7 C 0.5966(4) 0.1645(2) 0.45660(13) 0.0311(6) Uani 1 1 d . . . . .
H7 H 0.533737 0.128611 0.422096 0.037 Uiso 1 1 calc R . . . .
C8 C 0.3958(3) 0.3066(2) 0.35293(11) 0.0207(5) Uani 1 1 d . . . . .
H8 H 0.422226 0.229257 0.343746 0.025 Uiso 1 1 calc R . . . .
C9 C 0.3865(3) 0.3739(2) 0.29101(11) 0.0215(5) Uani 1 1 d . . . . .
H9 H 0.399991 0.452019 0.303322 0.026 Uiso 1 1 calc R . . . .
C10 C 0.1902(3) 0.3579(2) 0.26148(11) 0.0215(5) Uani 1 1 d . . . . .
C11 C 0.0896(4) 0.3705(2) 0.32046(12) 0.0279(6) Uani 1 1 d . . . . .
H11A H -0.025286 0.335093 0.313084 0.033 Uiso 1 1 calc R . . . .
H11B H 0.072911 0.448140 0.329971 0.033 Uiso 1 1 calc R . . . .
C12 C 0.2067(3) 0.3132(2) 0.37606(12) 0.0247(5) Uani 1 1 d . . . . .
H12 H 0.213034 0.360813 0.413857 0.030 Uiso 1 1 calc R . . . .
C13 C 0.1375(4) 0.2021(2) 0.39225(13) 0.0307(6) Uani 1 1 d . . . . .
H13 H 0.125549 0.148751 0.360295 0.037 Uiso 1 1 calc R . . . .
C14 C 0.0925(4) 0.1744(3) 0.44797(15) 0.0412(7) Uani 1 1 d . . . . .
H14A H 0.102640 0.225629 0.481103 0.049 Uiso 1 1 calc R . . . .
H14B H 0.050431 0.103531 0.454459 0.049 Uiso 1 1 calc R . . . .
C15 C 0.1376(3) 0.4423(2) 0.21241(11) 0.0224(5) Uani 1 1 d . . . . .
C16 C 0.1647(3) 0.2467(2) 0.23251(11) 0.0229(5) Uani 1 1 d . . . . .
C17 C 0.5211(3) 0.3505(2) 0.24583(11) 0.0230(5) Uani 1 1 d . . . . .
C18 C 0.5835(4) 0.2442(2) 0.23507(13) 0.0294(6) Uani 1 1 d . . . . .
H18 H 0.548852 0.184832 0.258748 0.035 Uiso 1 1 calc R . . . .
C19 C 0.6962(4) 0.2266(3) 0.18951(14) 0.0380(7) Uani 1 1 d . . . . .
H19 H 0.737376 0.155554 0.182882 0.046 Uiso 1 1 calc R . . . .
C20 C 0.7483(4) 0.3134(3) 0.15382(14) 0.0424(8) Uani 1 1 d . . . . .
H20 H 0.822241 0.300729 0.122592 0.051 Uiso 1 1 calc R . . . .
C21 C 0.6903(4) 0.4197(3) 0.16455(14) 0.0390(7) Uani 1 1 d . . . . .
H21 H 0.726372 0.478733 0.140933 0.047 Uiso 1 1 calc R . . . .
C22 C 0.5784(3) 0.4379(2) 0.21048(12) 0.0293(6) Uani 1 1 d . . . . .
H22 H 0.540942 0.509595 0.217857 0.035 Uiso 1 1 calc R . . . .


_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 1.5935(19) . ?
S1 O2 1.418(2) . ?
S1 O3 1.413(2) . ?
S1 N1 1.629(2) . ?
O1 C3 1.397(3) . ?
N1 C1 1.293(3) . ?
N2 C15 1.137(3) . ?
N3 C16 1.141(3) . ?
C1 C2 1.470(3) . ?
C1 C8 1.508(3) . ?
C2 C3 1.399(3) . ?
C2 C7 1.398(4) . ?
C3 C4 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.534(3) . ?
C8 C12 1.579(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.562(3) . ?
C9 C17 1.509(3) . ?
C10 C11 1.547(3) . ?
C10 C15 1.475(3) . ?
C10 C16 1.479(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.550(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.496(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.308(4) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C17 C18 1.397(4) . ?
C17 C22 1.393(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9300 . ?

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 104.42(11) . . ?
O2 S1 O1 104.24(12) . . ?
O2 S1 N1 109.16(12) . . ?
O3 S1 O1 109.47(12) . . ?
O3 S1 O2 119.84(13) . . ?
O3 S1 N1 108.61(11) . . ?
C3 O1 S1 116.25(16) . . ?
C1 N1 S1 120.22(18) . . ?
N1 C1 C2 123.0(2) . . ?
N1 C1 C8 116.0(2) . . ?
C2 C1 C8 120.9(2) . . ?
C3 C2 C1 118.9(2) . . ?
C7 C2 C1 123.8(2) . . ?
C7 C2 C3 117.3(2) . . ?
O1 C3 C2 119.8(2) . . ?
C4 C3 O1 117.3(2) . . ?
C4 C3 C2 122.9(3) . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C1 C8 H8 109.0 . . ?
C1 C8 C9 111.6(2) . . ?
C1 C8 C12 111.45(19) . . ?
C9 C8 H8 109.0 . . ?
C9 C8 C12 106.63(19) . . ?
C12 C8 H8 109.0 . . ?
C8 C9 H9 106.9 . . ?
C8 C9 C10 102.67(19) . . ?
C10 C9 H9 106.9 . . ?
C17 C9 C8 118.3(2) . . ?
C17 C9 H9 106.9 . . ?
C17 C9 C10 114.52(19) . . ?
C11 C10 C9 102.09(19) . . ?
C15 C10 C9 111.2(2) . . ?
C15 C10 C11 112.3(2) . . ?
C15 C10 C16 109.0(2) . . ?
C16 C10 C9 110.5(2) . . ?
C16 C10 C11 111.7(2) . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C10 C11 C12 105.7(2) . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C8 C12 H12 108.9 . . ?
C11 C12 C8 104.61(19) . . ?
C11 C12 H12 108.9 . . ?
C13 C12 C8 112.7(2) . . ?
C13 C12 C11 112.7(2) . . ?
C13 C12 H12 108.9 . . ?
C12 C13 H13 117.5 . . ?
C14 C13 C12 124.9(3) . . ?
C14 C13 H13 117.5 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
N2 C15 C10 177.4(3) . . ?
N3 C16 C10 177.2(3) . . ?
C18 C17 C9 123.1(2) . . ?
C22 C17 C9 118.5(2) . . ?
C22 C17 C18 118.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.0(3) . . ?
C21 C22 H22 119.5 . . ?

_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_mx5901
_database_code_depnum_ccdc_archive 'CCDC 1849602'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2018-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N3 O3 S'
_chemical_formula_sum            'C22 H17 N3 O3 S'
_chemical_formula_weight         403.44
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2461(16)
_cell_length_b                   10.300(2)
_cell_length_c                   12.879(3)
_cell_angle_alpha                104.17(3)
_cell_angle_beta                 99.94(3)
_cell_angle_gamma                105.52(3)
_cell_volume                     988.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4720
_cell_measurement_theta_min      2.2943
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13604
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         1.687
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4056
_reflns_number_total             4495
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.6963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1254
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
3.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
;
_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 0.17657(7) 0.39176(5) 0.42793(4) 0.02776(14) Uani 1 1 d . . . . .
O1 O 0.35259(19) 0.36138(15) 0.41119(11) 0.0307(3) Uani 1 1 d . . . . .
O2 O 0.1651(2) 0.49436(16) 0.37359(12) 0.0336(4) Uani 1 1 d . . . . .
O3 O 0.0398(2) 0.26053(16) 0.39396(13) 0.0384(4) Uani 1 1 d . . . . .
N1 N 0.3973(3) 0.6073(2) 1.05842(16) 0.0428(5) Uani 1 1 d . . . . .
N2 N -0.0335(3) 0.7221(2) 0.92808(18) 0.0448(5) Uani 1 1 d . . . . .
N3 N 0.2119(2) 0.46107(17) 0.56110(13) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.4257(3) 0.2981(2) 0.48312(16) 0.0263(4) Uani 1 1 d . . . . .
C2 C 0.5259(3) 0.2191(2) 0.44453(18) 0.0318(5) Uani 1 1 d . . . . .
H2 H 0.536270 0.203394 0.372084 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6106(3) 0.1639(2) 0.51591(19) 0.0338(5) Uani 1 1 d . . . . .
H3 H 0.680076 0.111214 0.491636 0.041 Uiso 1 1 calc R . . . .
C4 C 0.5932(3) 0.1862(2) 0.62370(18) 0.0313(5) Uani 1 1 d . . . . .
H4 H 0.649293 0.147134 0.670747 0.038 Uiso 1 1 calc R . . . .
C5 C 0.4932(3) 0.2661(2) 0.66095(16) 0.0275(4) Uani 1 1 d . . . . .
H5 H 0.483045 0.281047 0.733412 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4062(2) 0.3252(2) 0.59139(15) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.3060(2) 0.41704(19) 0.62752(15) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.3024(3) 0.4590(2) 0.74798(16) 0.0245(4) Uani 1 1 d . . . . .
H8 H 0.418935 0.477230 0.793832 0.029 Uiso 1 1 calc R . . . .
C9 C 0.1696(3) 0.3360(2) 0.77308(19) 0.0340(5) Uani 1 1 d . . . . .
H9 H 0.235050 0.304554 0.827489 0.041 Uiso 1 1 calc R . . . .
C10 C 0.0513(3) 0.4076(2) 0.82906(18) 0.0313(5) Uani 1 1 d . . . . .
H10A H -0.054353 0.394696 0.775279 0.038 Uiso 1 1 calc R . . . .
H10B H 0.019969 0.368359 0.886836 0.038 Uiso 1 1 calc R . . . .
C11 C 0.1604(3) 0.5652(2) 0.87818(16) 0.0259(4) Uani 1 1 d . . . . .
C12 C 0.2483(2) 0.5920(2) 0.78362(15) 0.0227(4) Uani 1 1 d . . . . .
H12 H 0.156709 0.587233 0.721808 0.027 Uiso 1 1 calc R . . . .
C13 C 0.0635(3) 0.2091(3) 0.6774(2) 0.0482(6) Uani 1 1 d . U . . .
H13 H 0.011020 0.224488 0.613641 0.058 Uiso 1 1 calc R . . . .
C14 C 0.0383(4) 0.0782(3) 0.6761(4) 0.0820(12) Uani 1 1 d . U . . .
H14A H 0.088591 0.058399 0.738256 0.098 Uiso 1 1 calc R . . . .
H14B H -0.029915 0.004503 0.612928 0.098 Uiso 1 1 calc R . . . .
C15 C 0.3860(2) 0.7358(2) 0.81543(15) 0.0235(4) Uani 1 1 d . . . . .
C16 C 0.3314(3) 0.8514(2) 0.80887(17) 0.0283(4) Uani 1 1 d . . . . .
H16 H 0.213462 0.837683 0.783877 0.034 Uiso 1 1 calc R . . . .
C17 C 0.4508(3) 0.9862(2) 0.83919(18) 0.0353(5) Uani 1 1 d . . . . .
H17 H 0.412566 1.062442 0.835208 0.042 Uiso 1 1 calc R . . . .
C18 C 0.6259(3) 1.0076(2) 0.87520(19) 0.0384(5) Uani 1 1 d . . . . .
H18 H 0.706027 1.097971 0.894828 0.046 Uiso 1 1 calc R . . . .
C19 C 0.6822(3) 0.8945(3) 0.8821(2) 0.0410(6) Uani 1 1 d . . . . .
H19 H 0.800396 0.908802 0.906251 0.049 Uiso 1 1 calc R . . . .
C20 C 0.5627(3) 0.7595(2) 0.85300(18) 0.0326(5) Uani 1 1 d . . . . .
H20 H 0.601644 0.684156 0.858770 0.039 Uiso 1 1 calc R . . . .
C21 C 0.2944(3) 0.5903(2) 0.98090(16) 0.0298(4) Uani 1 1 d . . . . .
C22 C 0.0527(3) 0.6555(2) 0.90551(17) 0.0307(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
S1 O1 1.6028(16) . ?
S1 O2 1.4172(15) . ?
S1 O3 1.4195(17) . ?
S1 N3 1.6288(18) . ?
O1 C1 1.400(2) . ?
N1 C21 1.136(3) . ?
N2 C22 1.139(3) . ?
N3 C7 1.300(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.399(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C6 C7 1.460(3) . ?
C7 C8 1.513(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.578(3) . ?
C8 C12 1.541(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.544(3) . ?
C9 C13 1.490(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.537(3) . ?
C11 C12 1.565(3) . ?
C11 C21 1.487(3) . ?
C11 C22 1.472(3) . ?
C12 H12 0.9800 . ?
C12 C15 1.515(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.304(4) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C16 1.397(3) . ?
C15 C20 1.387(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9300 . ?

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 N3 104.95(9) . . ?
O2 S1 O1 104.33(9) . . ?
O2 S1 O3 119.56(9) . . ?
O2 S1 N3 110.16(9) . . ?
O3 S1 O1 108.63(9) . . ?
O3 S1 N3 108.22(10) . . ?
C1 O1 S1 116.74(13) . . ?
C7 N3 S1 118.94(14) . . ?
C2 C1 O1 116.76(18) . . ?
C2 C1 C6 123.05(18) . . ?
C6 C1 O1 120.00(17) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.09(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.06(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 116.74(18) . . ?
C1 C6 C7 119.48(17) . . ?
C5 C6 C7 123.71(18) . . ?
N3 C7 C6 123.83(17) . . ?
N3 C7 C8 117.02(17) . . ?
C6 C7 C8 119.08(16) . . ?
C7 C8 H8 108.5 . . ?
C7 C8 C9 110.71(16) . . ?
C7 C8 C12 113.58(16) . . ?
C9 C8 H8 108.5 . . ?
C12 C8 H8 108.5 . . ?
C12 C8 C9 106.82(16) . . ?
C8 C9 H9 108.1 . . ?
C10 C9 C8 104.45(16) . . ?
C10 C9 H9 108.1 . . ?
C13 C9 C8 117.19(19) . . ?
C13 C9 H9 108.1 . . ?
C13 C9 C10 110.66(19) . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C9 105.02(17) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C10 C11 C12 102.00(16) . . ?
C21 C11 C10 110.94(17) . . ?
C21 C11 C12 110.52(16) . . ?
C22 C11 C10 112.18(17) . . ?
C22 C11 C12 113.20(17) . . ?
C22 C11 C21 107.98(17) . . ?
C8 C12 C11 102.23(15) . . ?
C8 C12 H12 107.2 . . ?
C11 C12 H12 107.2 . . ?
C15 C12 C8 118.37(16) . . ?
C15 C12 C11 114.00(16) . . ?
C15 C12 H12 107.2 . . ?
C9 C13 H13 117.4 . . ?
C14 C13 C9 125.1(3) . . ?
C14 C13 H13 117.4 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C16 C15 C12 118.01(17) . . ?
C20 C15 C12 123.67(18) . . ?
C20 C15 C16 118.30(19) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.75(19) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.8(2) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N1 C21 C11 178.7(2) . . ?
N2 C22 C11 177.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
