# Electronic Supplementary Material (ESI) for ChemComm.
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1885455'
loop_
_audit_author_name
_audit_author_address
'youliang shao'
;lanzhou university
China
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 N2 O5 S'
_chemical_formula_sum            'C16 H16 N2 O5 S'
_chemical_formula_weight         348.37
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   9.5967(8)
_cell_length_b                   14.6083(12)
_cell_length_c                   24.1283(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3382.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6716
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.708
_cell_measurement_theta_min      2.676
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1142 before and 0.0463 after correction. The Ratio of minimum to maximum transmission is 0.9012. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17493
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.69
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2779
_reflns_number_total             3319
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0446P)²+1.3264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.69696(4) 0.04977(3) 0.399283(17) 0.03764(13) Uani 1 d . . .
O1 O 0.48876(14) 0.14927(12) 0.31901(7) 0.0730(5) Uani 1 d . . .
O2 O 0.68586(15) 0.14525(10) 0.26885(5) 0.0609(4) Uani 1 d . . .
O3 O 0.90784(13) 0.34841(9) 0.33106(6) 0.0536(3) Uani 1 d . . .
O4 O 0.68023(12) 0.32734(9) 0.31397(5) 0.0482(3) Uani 1 d . . .
O5 O 0.79973(14) 0.35769(8) 0.45498(5) 0.0518(3) Uani 1 d . . .
N1 N 1.00119(13) 0.16544(9) 0.41423(5) 0.0350(3) Uani 1 d . . .
N2 N 0.88436(13) 0.22650(8) 0.42135(5) 0.0352(3) Uani 1 d . . .
C1 C 1.07432(15) 0.01085(11) 0.41476(6) 0.0327(3) Uani 1 d . . .
C2 C 1.03374(17) -0.07899(12) 0.40567(7) 0.0418(4) Uani 1 d . . .
H2 H 0.9408 -0.0955 0.4102 0.050 Uiso 1 calc . . R
C3 C 1.1307(2) -0.14453(13) 0.38993(8) 0.0515(5) Uani 1 d . . .
H3 H 1.1022 -0.2044 0.3833 0.062 Uiso 1 calc . . R
C4 C 1.2684(2) -0.12114(14) 0.38416(8) 0.0542(5) Uani 1 d . . .
H4 H 1.3333 -0.1651 0.3737 0.065 Uiso 1 calc . . R
C5 C 1.31029(19) -0.03240(15) 0.39393(9) 0.0557(5) Uani 1 d . . .
H5 H 1.4038 -0.0169 0.3903 0.067 Uiso 1 calc . . R
C6 C 1.21485(17) 0.03366(13) 0.40897(7) 0.0444(4) Uani 1 d . . .
H6 H 1.2441 0.0935 0.4153 0.053 Uiso 1 calc . . R
C7 C 0.96934(15) 0.08244(10) 0.42728(6) 0.0310(3) Uani 1 d . . .
C8 C 0.83111(15) 0.05692(11) 0.45202(6) 0.0343(3) Uani 1 d . . .
H8A H 0.8047 0.1023 0.4794 0.041 Uiso 1 calc . . R
H8B H 0.8393 -0.0017 0.4707 0.041 Uiso 1 calc . . R
C9 C 0.70757(15) 0.15477(11) 0.36487(6) 0.0332(3) Uani 1 d . . .
C10 C 0.78824(15) 0.22723(10) 0.37639(6) 0.0331(3) Uani 1 d . . .
C11 C 0.61254(18) 0.15113(12) 0.31504(7) 0.0432(4) Uani 1 d . . .
C12 C 0.6067(4) 0.1429(2) 0.21738(10) 0.0996(10) Uani 1 d . . .
H12A H 0.6698 0.1403 0.1865 0.149 Uiso 1 calc . . GR
H12B H 0.5504 0.1970 0.2146 0.149 Uiso 1 calc . . GR
H12C H 0.5478 0.0898 0.2171 0.149 Uiso 1 calc . . GR
C13 C 0.80081(16) 0.30796(11) 0.33850(6) 0.0370(4) Uani 1 d . . .
C14 C 0.6838(3) 0.39651(16) 0.27102(10) 0.0739(7) Uani 1 d . . .
H14A H 0.7536 0.3808 0.2442 0.111 Uiso 1 calc . . GR
H14B H 0.7056 0.4548 0.2872 0.111 Uiso 1 calc . . GR
H14C H 0.5944 0.3997 0.2532 0.111 Uiso 1 calc . . GR
C15 C 0.89207(17) 0.30004(11) 0.45615(6) 0.0379(4) Uani 1 d . . .
C16 C 1.0113(2) 0.30228(14) 0.49587(8) 0.0536(5) Uani 1 d . . .
H16A H 1.0130 0.3603 0.5145 0.080 Uiso 1 calc . . GR
H16B H 1.0970 0.2938 0.4760 0.080 Uiso 1 calc . . GR
H16C H 1.0005 0.2542 0.5226 0.080 Uiso 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 C8 1.8132(15) . ?
S1 C9 1.7471(16) . ?
O1 C11 1.192(2) . ?
O2 C11 1.321(2) . ?
O2 C12 1.456(2) . ?
O3 C13 1.1984(19) . ?
O4 C13 1.3302(19) . ?
O4 C14 1.448(2) . ?
O5 C15 1.223(2) . ?
N1 N2 1.4430(17) . ?
N1 C7 1.2895(19) . ?
N2 C10 1.4240(19) . ?
N2 C15 1.365(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.396(2) . ?
C1 C7 1.483(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.502(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.341(2) . ?
C9 C11 1.510(2) . ?
C10 C13 1.497(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.493(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C8 103.98(7) . . ?
C11 O2 C12 116.31(19) . . ?
C13 O4 C14 116.52(15) . . ?
C7 N1 N2 111.58(12) . . ?
C10 N2 N1 114.66(11) . . ?
C15 N2 N1 121.16(12) . . ?
C15 N2 C10 119.84(13) . . ?
C2 C1 C6 118.78(15) . . ?
C2 C1 C7 120.58(14) . . ?
C6 C1 C7 120.54(15) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.53(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.10(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.89(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.63(17) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.05(17) . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C1 116.89(13) . . ?
N1 C7 C8 122.68(14) . . ?
C1 C7 C8 120.40(13) . . ?
S1 C8 H8A 109.4 . . ?
S1 C8 H8B 109.4 . . ?
C7 C8 S1 111.25(10) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 S1 128.93(12) . . ?
C10 C9 C11 122.80(14) . . ?
C11 C9 S1 108.19(11) . . ?
N2 C10 C13 114.77(13) . . ?
C9 C10 N2 121.74(14) . . ?
C9 C10 C13 122.82(14) . . ?
O1 C11 O2 126.66(17) . . ?
O1 C11 C9 122.60(17) . . ?
O2 C11 C9 110.63(14) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 125.04(15) . . ?
O3 C13 C10 123.29(14) . . ?
O4 C13 C10 111.67(13) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 N2 119.24(14) . . ?
O5 C15 C16 123.71(15) . . ?
N2 C15 C16 116.97(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C9 C10 N2 1.0(2) . . . . ?
S1 C9 C10 C13 171.13(12) . . . . ?
S1 C9 C11 O1 69.2(2) . . . . ?
S1 C9 C11 O2 -107.34(14) . . . . ?
N1 N2 C10 C9 68.48(19) . . . . ?
N1 N2 C10 C13 -102.36(14) . . . . ?
N1 N2 C15 O5 169.12(14) . . . . ?
N1 N2 C15 C16 -14.0(2) . . . . ?
N1 C7 C8 S1 79.38(16) . . . . ?
N2 N1 C7 C1 172.11(11) . . . . ?
N2 N1 C7 C8 -5.60(19) . . . . ?
N2 C10 C13 O3 28.4(2) . . . . ?
N2 C10 C13 O4 -152.62(13) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C7 C8 S1 -98.25(14) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 C7 N1 -153.65(15) . . . . ?
C2 C1 C7 C8 24.1(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C6 C1 C7 N1 22.9(2) . . . . ?
C6 C1 C7 C8 -159.35(14) . . . . ?
C7 N1 N2 C10 -82.25(16) . . . . ?
C7 N1 N2 C15 121.20(15) . . . . ?
C7 C1 C2 C3 175.19(15) . . . . ?
C7 C1 C6 C5 -175.95(16) . . . . ?
C8 S1 C9 C10 -4.23(16) . . . . ?
C8 S1 C9 C11 172.63(11) . . . . ?
C9 S1 C8 C7 -52.87(12) . . . . ?
C9 C10 C13 O3 -142.28(17) . . . . ?
C9 C10 C13 O4 36.7(2) . . . . ?
C10 N2 C15 O5 13.8(2) . . . . ?
C10 N2 C15 C16 -169.32(14) . . . . ?
C10 C9 C11 O1 -113.7(2) . . . . ?
C10 C9 C11 O2 69.8(2) . . . . ?
C11 C9 C10 N2 -175.40(14) . . . . ?
C11 C9 C10 C13 -5.3(2) . . . . ?
C12 O2 C11 O1 4.7(3) . . . . ?
C12 O2 C11 C9 -178.92(18) . . . . ?
C14 O4 C13 O3 6.7(3) . . . . ?
C14 O4 C13 C10 -172.25(16) . . . . ?
C15 N2 C10 C9 -134.64(16) . . . . ?
C15 N2 C10 C13 54.53(19) . . . . ?

_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_liyt_2_90_3
_database_code_depnum_ccdc_archive 'CCDC 1887981'
loop_
_audit_author_name
_audit_author_address
'youliang shao'
;lanzhou university
China
;
_audit_update_record             
;
2018-12-30 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2017-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O7 S'
_chemical_formula_sum            'C16 H16 N2 O7 S'
_chemical_formula_weight         380.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1191(7)
_cell_length_b                   26.9873(15)
_cell_length_c                   7.2702(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.108(7)
_cell_angle_gamma                90
_cell_volume                     1727.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1167
_cell_measurement_temperature    292.46(10)
_cell_measurement_theta_max      24.6590
_cell_measurement_theta_min      3.9140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6354
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.544
_diffrn_ambient_temperature      292.46(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -59.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00   54.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   90.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  150.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0783122000
_diffrn_orient_matrix_UB_12      0.0001686000
_diffrn_orient_matrix_UB_13      0.0484690000
_diffrn_orient_matrix_UB_21      -0.0139595000
_diffrn_orient_matrix_UB_22      0.0184498000
_diffrn_orient_matrix_UB_23      0.0628203000
_diffrn_orient_matrix_UB_31      -0.0128043000
_diffrn_orient_matrix_UB_32      -0.0187474000
_diffrn_orient_matrix_UB_33      0.0624595000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2257
_reflns_number_total             3395
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.047
_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)+(0.0399P)²+0.3533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.47497(8) 0.16708(3) 0.89025(11) 0.0364(2) Uani 1 1 d . . . . .
O1 O 0.7678(3) 0.01557(8) 0.8579(4) 0.0579(7) Uani 1 1 d . . . . .
O2 O 0.8464(2) 0.04473(8) 1.2774(3) 0.0531(6) Uani 1 1 d . . . . .
O3 O 0.6047(2) 0.01745(7) 1.1909(3) 0.0465(6) Uani 1 1 d . . . . .
O4 O 0.5333(2) 0.10627(9) 1.3679(3) 0.0520(6) Uani 1 1 d . . . . .
O5 O 0.3196(2) 0.11211(8) 1.1309(3) 0.0483(6) Uani 1 1 d . . . . .
O6 O 0.3378(2) 0.15104(8) 0.7579(3) 0.0495(6) Uani 1 1 d . . . . .
O7 O 0.4702(2) 0.20984(7) 1.0063(3) 0.0481(6) Uani 1 1 d . . . . .
N1 N 0.7632(3) 0.09699(8) 0.9200(4) 0.0355(6) Uani 1 1 d . . . . .
N2 N 0.8494(3) 0.14232(8) 0.9478(4) 0.0352(6) Uani 1 1 d . . . . .
C1 C 0.6660(3) 0.08852(10) 1.0392(4) 0.0324(7) Uani 1 1 d . . . . .
C2 C 0.5485(3) 0.11745(10) 1.0475(4) 0.0337(7) Uani 1 1 d . . . . .
C3 C 0.6105(3) 0.17698(11) 0.7596(4) 0.0354(7) Uani 1 1 d . . . . .
H3A H 0.6035 0.1499 0.6698 0.042 Uiso 1 1 calc R . . . .
H3B H 0.5843 0.2072 0.6865 0.042 Uiso 1 1 calc R . . . .
C4 C 0.7729(3) 0.18090(10) 0.8768(4) 0.0316(7) Uani 1 1 d . . . . .
C5 C 0.8293(4) 0.05559(11) 0.8570(5) 0.0432(8) Uani 1 1 d . . . . .
C6 C 0.9649(4) 0.06386(12) 0.7821(6) 0.0556(10) Uani 1 1 d . . . . .
H6A H 0.9353 0.0821 0.6649 0.083 Uiso 1 1 calc GR . . . .
H6B H 1.0066 0.0325 0.7596 0.083 Uiso 1 1 calc GR . . . .
H6C H 1.0399 0.0823 0.8736 0.083 Uiso 1 1 calc GR . . . .
C7 C 0.7179(3) 0.04699(10) 1.1824(4) 0.0368(7) Uani 1 1 d . . . . .
C8 C 0.6390(5) -0.02007(12) 1.3357(6) 0.0652(11) Uani 1 1 d . . . . .
H8A H 0.7083 -0.0437 1.3061 0.098 Uiso 1 1 calc GR . . . .
H8B H 0.5470 -0.0366 1.3412 0.098 Uiso 1 1 calc GR . . . .
H8C H 0.6845 -0.0050 1.4568 0.098 Uiso 1 1 calc GR . . . .
C9 C 0.4684(3) 0.11090(10) 1.2029(5) 0.0366(7) Uani 1 1 d . . . . .
C10 C 0.2270(4) 0.10844(14) 1.2659(5) 0.0612(10) Uani 1 1 d . . . . .
H10A H 0.1257 0.1195 1.2062 0.092 Uiso 1 1 calc GR . . . .
H10B H 0.2700 0.1288 1.3749 0.092 Uiso 1 1 calc GR . . . .
H10C H 0.2242 0.0746 1.3057 0.092 Uiso 1 1 calc GR . . . .
C11 C 0.8534(3) 0.22900(10) 0.9094(4) 0.0316(7) Uani 1 1 d . . . . .
C12 C 0.7734(3) 0.27340(10) 0.8942(4) 0.0384(7) Uani 1 1 d . . . . .
H12 H 0.6678 0.2731 0.8575 0.046 Uiso 1 1 calc R . . . .
C13 C 0.8507(4) 0.31819(11) 0.9335(5) 0.0428(8) Uani 1 1 d . . . . .
H13 H 0.7972 0.3478 0.9234 0.051 Uiso 1 1 calc R . . . .
C14 C 1.0068(4) 0.31835(11) 0.9875(5) 0.0478(9) Uani 1 1 d . . . . .
H14 H 1.0589 0.3481 1.0169 0.057 Uiso 1 1 calc R . . . .
C15 C 1.0867(4) 0.27451(12) 0.9984(5) 0.0515(9) Uani 1 1 d . . . . .
H15 H 1.1923 0.2750 1.0317 0.062 Uiso 1 1 calc R . . . .
C16 C 1.0110(3) 0.23005(11) 0.9603(5) 0.0441(8) Uani 1 1 d . . . . .
H16 H 1.0655 0.2006 0.9687 0.053 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 O6 1.432(2) . ?
S1 O7 1.437(2) . ?
S1 C2 1.775(3) . ?
S1 C3 1.764(3) . ?
O1 C5 1.218(3) . ?
O2 C7 1.196(3) . ?
O3 C7 1.319(3) . ?
O3 C8 1.436(4) . ?
O4 C9 1.198(4) . ?
O5 C9 1.321(3) . ?
O5 C10 1.456(4) . ?
N1 N2 1.439(3) . ?
N1 C1 1.411(3) . ?
N1 C5 1.402(4) . ?
N2 C4 1.284(3) . ?
C1 C2 1.340(4) . ?
C1 C7 1.519(4) . ?
C2 C9 1.507(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.507(4) . ?
C4 C11 1.480(4) . ?
C5 C6 1.492(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.392(4) . ?
C11 C16 1.388(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(4) . ?
C16 H16 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
O6 S1 O7 118.87(14) . . ?
O6 S1 C2 108.77(13) . . ?
O6 S1 C3 107.21(14) . . ?
O7 S1 C2 106.97(14) . . ?
O7 S1 C3 109.09(14) . . ?
C3 S1 C2 105.12(14) . . ?
C7 O3 C8 115.9(3) . . ?
C9 O5 C10 116.6(3) . . ?
C1 N1 N2 117.3(2) . . ?
C5 N1 N2 117.3(2) . . ?
C5 N1 C1 117.6(2) . . ?
C4 N2 N1 114.4(2) . . ?
N1 C1 C7 114.0(2) . . ?
C2 C1 N1 124.8(3) . . ?
C2 C1 C7 120.6(3) . . ?
C1 C2 S1 125.7(2) . . ?
C1 C2 C9 121.0(3) . . ?
C9 C2 S1 113.3(2) . . ?
S1 C3 H3A 108.4 . . ?
S1 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 S1 115.4(2) . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N2 C4 C3 121.4(2) . . ?
N2 C4 C11 116.9(2) . . ?
C11 C4 C3 121.7(2) . . ?
O1 C5 N1 117.8(3) . . ?
O1 C5 C6 124.2(3) . . ?
N1 C5 C6 117.9(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O3 127.1(3) . . ?
O2 C7 C1 121.1(3) . . ?
O3 C7 C1 111.7(3) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 O5 126.0(3) . . ?
O4 C9 C2 123.6(3) . . ?
O5 C9 C2 110.4(3) . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 121.0(2) . . ?
C16 C11 C4 119.8(2) . . ?
C16 C11 C12 119.2(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H16 119.9 . . ?

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 C2 C9 O4 -131.8(3) . . . . ?
S1 C2 C9 O5 46.9(3) . . . . ?
S1 C3 C4 N2 76.6(3) . . . . ?
S1 C3 C4 C11 -105.8(3) . . . . ?
O6 S1 C2 C1 103.1(3) . . . . ?
O6 S1 C2 C9 -78.8(2) . . . . ?
O6 S1 C3 C4 -164.5(2) . . . . ?
O7 S1 C2 C1 -127.3(3) . . . . ?
O7 S1 C2 C9 50.7(2) . . . . ?
O7 S1 C3 C4 65.6(2) . . . . ?
N1 N2 C4 C3 -5.3(4) . . . . ?
N1 N2 C4 C11 177.0(2) . . . . ?
N1 C1 C2 S1 9.0(4) . . . . ?
N1 C1 C2 C9 -168.9(3) . . . . ?
N1 C1 C7 O2 47.8(4) . . . . ?
N1 C1 C7 O3 -135.1(3) . . . . ?
N2 N1 C1 C2 61.3(4) . . . . ?
N2 N1 C1 C7 -110.4(3) . . . . ?
N2 N1 C5 O1 170.1(3) . . . . ?
N2 N1 C5 C6 -13.5(4) . . . . ?
N2 C4 C11 C12 -159.4(3) . . . . ?
N2 C4 C11 C16 19.1(4) . . . . ?
C1 N1 N2 C4 -77.6(3) . . . . ?
C1 N1 C5 O1 21.6(4) . . . . ?
C1 N1 C5 C6 -162.0(3) . . . . ?
C1 C2 C9 O4 46.4(4) . . . . ?
C1 C2 C9 O5 -135.0(3) . . . . ?
C2 S1 C3 C4 -48.9(2) . . . . ?
C2 C1 C7 O2 -124.2(3) . . . . ?
C2 C1 C7 O3 52.8(4) . . . . ?
C3 S1 C2 C1 -11.4(3) . . . . ?
C3 S1 C2 C9 166.6(2) . . . . ?
C3 C4 C11 C12 22.9(4) . . . . ?
C3 C4 C11 C16 -158.6(3) . . . . ?
C4 C11 C12 C13 177.1(3) . . . . ?
C4 C11 C16 C15 -177.4(3) . . . . ?
C5 N1 N2 C4 133.8(3) . . . . ?
C5 N1 C1 C2 -150.2(3) . . . . ?
C5 N1 C1 C7 38.1(4) . . . . ?
C7 C1 C2 S1 -179.8(2) . . . . ?
C7 C1 C2 C9 2.3(4) . . . . ?
C8 O3 C7 O2 2.8(5) . . . . ?
C8 O3 C7 C1 -174.0(3) . . . . ?
C10 O5 C9 O4 1.3(5) . . . . ?
C10 O5 C9 C2 -177.4(2) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C11 C16 C15 1.1(5) . . . . ?
C12 C13 C14 C15 1.5(5) . . . . ?
C13 C14 C15 C16 -1.8(5) . . . . ?
C14 C15 C16 C11 0.4(5) . . . . ?
C16 C11 C12 C13 -1.4(5) . . . . ?

_olex2_date_sample_data_collection 2017-10-13
_olex2_submission_special_instructions 'No special instructions were received'
