# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_200109b_0m
_database_code_depnum_ccdc_archive 'CCDC 1978861'
loop_
_audit_author_name
_audit_author_address
'Gongyi Liu'
;Wuhan University
China
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-03-19 downloaded from the CCDC.
;
_audit_creation_date             2020-01-15
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C14 H13 N O4 S'
_chemical_formula_sum            'C14 H13 N O4 S'
_chemical_formula_weight         291.31
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   7.7349(14)
_cell_length_b                   9.6402(17)
_cell_length_c                   9.3298(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.782(3)
_cell_angle_gamma                90.00
_cell_volume                     681.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4278
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.44
_cell_measurement_theta_min      2.23
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
; 
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4701
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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                2195
_reflns_number_total             2238
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_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  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.142
_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)+(0.0404P)²+0.0725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0729
_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 N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Ternary CH refined with riding coordinates: 
 C7(H7) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13) 
2.c Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C) 
;
_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
C1 C 0.6596(2) 0.8030(2) 0.87463(18) 0.0383(4) Uani 1 d . . .
C2 C 0.7780(3) 0.8291(3) 1.0046(2) 0.0547(5) Uani 1 d . . .
H2 H 0.7980 0.7628 1.0785 0.066 Uiso 1 calc . . R
C3 C 0.8671(3) 0.9560(3) 1.0234(3) 0.0751(9) Uani 1 d . . .
H3 H 0.9474 0.9742 1.1101 0.090 Uiso 1 calc . . R
C4 C 0.8366(4) 1.0536(3) 0.9146(4) 0.0755(8) Uani 1 d . . .
H4 H 0.8959 1.1380 0.9280 0.091 Uiso 1 calc . . R
C5 C 0.7201(3) 1.0282(2) 0.7871(3) 0.0607(6) Uani 1 d . . .
H5 H 0.6998 1.0951 0.7138 0.073 Uiso 1 calc . . R
C6 C 0.6320(3) 0.9025(2) 0.7666(2) 0.0460(5) Uani 1 d . . .
H6 H 0.5533 0.8851 0.6789 0.055 Uiso 1 calc . . R
C7 C 0.5712(2) 0.66207(19) 0.85073(18) 0.0363(4) Uani 1 d . . .
H7 H 0.5715 0.6209 0.9468 0.044 Uiso 1 calc . . R
C8 C 0.3818(2) 0.6662(2) 0.76558(18) 0.0341(4) Uani 1 d . . .
C9 C 0.3156(2) 0.57672(18) 0.65108(19) 0.0360(4) Uani 1 d . . .
C10 C 0.1431(3) 0.5805(2) 0.5729(2) 0.0402(4) Uani 1 d . . .
H10 H 0.1042 0.5186 0.4966 0.048 Uiso 1 calc . . R
C11 C 0.0302(2) 0.6786(2) 0.61094(19) 0.0387(4) Uani 1 d . . .
C12 C 0.0887(2) 0.7678(2) 0.7277(2) 0.0405(4) Uani 1 d . . .
H12 H 0.0117 0.8322 0.7549 0.049 Uiso 1 calc . . R
C13 C 0.2612(2) 0.76053(19) 0.80309(19) 0.0384(4) Uani 1 d . . .
H13 H 0.2987 0.8203 0.8815 0.046 Uiso 1 calc . . R
C14 C -0.1966(3) 0.6289(3) 0.4012(2) 0.0717(7) Uani 1 d . . .
H14A H -0.1215 0.6596 0.3372 0.108 Uiso 1 calc . . GR
H14B H -0.3167 0.6535 0.3600 0.108 Uiso 1 calc . . GR
H14C H -0.1875 0.5300 0.4123 0.108 Uiso 1 calc . . GR
N1 N 0.6850(2) 0.57491(17) 0.77520(19) 0.0427(4) Uani 1 d . . .
H1 H 0.723(3) 0.625(2) 0.698(2) 0.051 Uiso 1 d . . R
O1 O 0.42220(18) 0.47508(14) 0.60178(15) 0.0493(4) Uani 1 d . . .
O2 O 0.7022(2) 0.36689(16) 0.62246(18) 0.0606(4) Uani 1 d . . .
O3 O 0.5488(2) 0.35580(16) 0.82921(17) 0.0630(4) Uani 1 d . . .
O4 O -0.14291(17) 0.69378(16) 0.54143(15) 0.0511(4) Uani 1 d . . .
S1 S 0.59803(6) 0.42987(5) 0.71289(5) 0.04474(15) Uani 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
C1 C2 1.385(3) . ?
C1 C6 1.376(3) . ?
C1 C7 1.517(3) . ?
C2 C3 1.398(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.360(4) . ?
C5 C6 1.384(3) . ?
C7 C8 1.517(2) . ?
C7 N1 1.494(2) . ?
C8 C9 1.387(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.384(3) . ?
C9 O1 1.417(2) . ?
C10 C11 1.382(3) . ?
C11 C12 1.389(3) . ?
C11 O4 1.371(2) . ?
C12 C13 1.378(3) . ?
C14 O4 1.433(3) . ?
N1 S1 1.6079(18) . ?
O1 S1 1.5933(14) . ?
O2 S1 1.4167(15) . ?
O3 S1 1.4147(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
C2 C1 C7 119.27(19) . . ?
C6 C1 C2 119.39(19) . . ?
C6 C1 C7 121.23(16) . . ?
C1 C2 C3 119.3(2) . . ?
C4 C3 C2 120.1(2) . . ?
C5 C4 C3 120.5(2) . . ?
C4 C5 C6 119.9(2) . . ?
C1 C6 C5 120.7(2) . . ?
C1 C7 C8 114.30(15) . . ?
N1 C7 C1 106.36(14) . . ?
N1 C7 C8 111.51(14) . . ?
C9 C8 C7 123.50(15) . . ?
C9 C8 C13 115.92(16) . . ?
C13 C8 C7 120.55(16) . . ?
C8 C9 O1 122.16(15) . . ?
C10 C9 C8 123.66(16) . . ?
C10 C9 O1 114.16(15) . . ?
C11 C10 C9 118.29(16) . . ?
C10 C11 C12 120.26(16) . . ?
O4 C11 C10 123.96(17) . . ?
O4 C11 C12 115.77(16) . . ?
C13 C12 C11 119.65(17) . . ?
C12 C13 C8 122.15(17) . . ?
C7 N1 S1 114.62(12) . . ?
C9 O1 S1 117.02(11) . . ?
C11 O4 C14 117.26(17) . . ?
O1 S1 N1 103.63(8) . . ?
O2 S1 N1 109.96(9) . . ?
O2 S1 O1 104.09(9) . . ?
O3 S1 N1 108.64(9) . . ?
O3 S1 O1 108.03(9) . . ?
O3 S1 O2 121.03(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.96(2) 2.07(2) 3.005(2) 165(2) 1_655

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
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C7 C8 C9 133.97(17) . . . . ?
C1 C7 C8 C13 -48.0(2) . . . . ?
C1 C7 N1 S1 -169.38(12) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C7 C8 144.50(17) . . . . ?
C2 C1 C7 N1 -92.01(19) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 C7 C8 -39.2(2) . . . . ?
C6 C1 C7 N1 84.3(2) . . . . ?
C7 C1 C2 C3 176.39(18) . . . . ?
C7 C1 C6 C5 -176.81(17) . . . . ?
C7 C8 C9 C10 -179.77(17) . . . . ?
C7 C8 C9 O1 -1.5(3) . . . . ?
C7 C8 C13 C12 179.59(16) . . . . ?
C7 N1 S1 O1 59.21(14) . . . . ?
C7 N1 S1 O2 169.98(12) . . . . ?
C7 N1 S1 O3 -55.49(15) . . . . ?
C8 C7 N1 S1 -44.16(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 O1 S1 20.9(2) . . . . ?
C9 C8 C13 C12 -2.3(2) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C9 C10 C11 O4 179.46(16) . . . . ?
C9 O1 S1 N1 -46.34(15) . . . . ?
C9 O1 S1 O2 -161.36(13) . . . . ?
C9 O1 S1 O3 68.81(15) . . . . ?
C10 C9 O1 S1 -160.69(13) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C10 C11 O4 C14 -15.9(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C12 C11 O4 C14 165.31(19) . . . . ?
C13 C8 C9 C10 2.2(2) . . . . ?
C13 C8 C9 O1 -179.58(16) . . . . ?
N1 C7 C8 C9 13.3(2) . . . . ?
N1 C7 C8 C13 -168.72(15) . . . . ?
O1 C9 C10 C11 -178.54(15) . . . . ?
O4 C11 C12 C13 -179.49(16) . . . . ?


_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_dongxq-liugongyi-lgy-5-104-3-rt-20200111
_database_code_depnum_ccdc_archive 'CCDC 1978862'
loop_
_audit_author_name
_audit_author_address
'Gongyi Liu'
;Wuhan University
China
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-03-19 downloaded from the CCDC.
;
_audit_creation_date             2020-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O5 S'
_chemical_formula_sum            'C9 H11 N O5 S'
_chemical_formula_weight         245.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'H C N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   7.15760(10)
_cell_length_b                   7.15760(10)
_cell_length_c                   37.3509(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1657.17(5)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    15515
_cell_measurement_temperature    298.98(13)
_cell_measurement_theta_max      71.4390
_cell_measurement_theta_min      3.5120
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    2.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            19791
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.279
_diffrn_reflns_theta_min         3.550
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.98(13)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  94.00   0.50    0.50    --    5.00  36.00 152.00  258
  2  ω    -35.00  94.00   0.50    0.50    --    5.00  36.00 152.00  258
  3  ω   -131.00  -7.00   0.50    0.50    --  -96.70  62.00 136.00  248
  4  ω    -82.00  42.00   0.50    0.50    --  -47.40  57.00   0.00  248
  5  ω   -137.00  -8.00   0.50    0.50    --  -47.40 -38.00 -90.00  258
  6  ω   -186.00 -62.00   0.50    0.50    --  -96.70 -57.00-120.00  248
  7  ω   -186.00 -57.00   0.50    0.50    --  -96.70 -38.00  30.00  258
  8  ω   -186.00 -57.00   0.50    0.50    --  -96.70 -38.00-180.00  258
  9  ω   -186.00 -62.00   0.50    0.50    --  -96.70 -62.00  -1.00  248
 10  ω   -131.00  -7.00   0.50    0.50    --  -96.70  57.00 150.00  248
 11  ω   -186.00 -56.00   0.50    0.50    --  -96.70 -36.00  -3.00  260
 12  ω   -186.00 -60.00   0.50    0.50    --  -96.70 -45.00 154.00  252
 13  ω   -137.00  -8.00   0.50    0.50    --  -47.40 -75.00-120.00  258
 14  ω   -137.00  -8.00   0.50    0.50    --  -47.40 -75.00  90.00  258
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from ω-scans and φ-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0890730000
_diffrn_orient_matrix_UB_12      -0.0309717000
_diffrn_orient_matrix_UB_13      0.0356987000
_diffrn_orient_matrix_UB_21      0.1063602000
_diffrn_orient_matrix_UB_22      -0.1108492000
_diffrn_orient_matrix_UB_23      -0.0200435000
_diffrn_orient_matrix_UB_31      0.2062594000
_diffrn_orient_matrix_UB_32      0.2201112000
_diffrn_orient_matrix_UB_33      -0.0050719000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2082
_reflns_number_total             2116
_reflns_odcompleteness_completeness 98.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection       
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_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         0.155
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.084
_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)+(0.0410P)²+0.1653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0685
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 -0.04377(9) 0.88800(9) 0.39293(2) 0.05074(16) Uani 1 1 d . . . . .
O3 O 0.1738(3) 1.0581(2) 0.38958(4) 0.0624(4) Uani 1 1 d . . . . .
O1 O -0.0712(2) 0.8015(3) 0.43291(3) 0.0556(4) Uani 1 1 d . . . . .
O5 O 0.2176(3) 0.6734(3) 0.31712(4) 0.0626(4) Uani 1 1 d . . . . .
O4 O 0.2195(3) 0.5564(3) 0.52496(4) 0.0743(5) Uani 1 1 d . . . . .
N1 N -0.0740(3) 0.6907(3) 0.36868(4) 0.0509(4) Uani 1 1 d . . . . .
O2 O -0.2157(3) 0.9280(3) 0.38737(4) 0.0781(6) Uani 1 1 d . . . . .
C7 C 0.0673(3) 0.6001(3) 0.37696(5) 0.0467(4) Uani 1 1 d . . . . .
C9 C 0.2702(3) 0.7083(4) 0.35413(5) 0.0514(4) Uani 1 1 d . . . . .
C2 C 0.0760(4) 0.6863(3) 0.47866(5) 0.0519(5) Uani 1 1 d . . . . .
C4 C 0.1148(3) 0.6056(3) 0.41658(5) 0.0459(4) Uani 1 1 d . . . . .
C3 C 0.0452(3) 0.6968(3) 0.44204(5) 0.0466(4) Uani 1 1 d . . . . .
C1 C 0.1824(4) 0.5817(4) 0.49001(5) 0.0565(5) Uani 1 1 d . . . . .
C5 C 0.2257(4) 0.5057(4) 0.42907(6) 0.0576(5) Uani 1 1 d . . . . .
C6 C 0.2607(5) 0.4938(4) 0.46493(6) 0.0666(6) Uani 1 1 d . . . . .
C8 C 0.1290(5) 0.6283(5) 0.55179(6) 0.0692(7) Uani 1 1 d . . . . .
H9A H 0.361(4) 0.647(4) 0.3584(7) 0.059(6) Uiso 1 1 d . . . . .
H9B H 0.358(4) 0.864(4) 0.3599(6) 0.056(6) Uiso 1 1 d . . . . .
H7 H -0.023(4) 0.453(4) 0.3694(5) 0.045(5) Uiso 1 1 d . . . . .
H5A H 0.293(4) 0.455(4) 0.4119(6) 0.066(7) Uiso 1 1 d . . . . .
H5 H 0.173(6) 0.733(6) 0.3114(8) 0.088(11) Uiso 1 1 d . . . . .
H6 H 0.333(5) 0.420(5) 0.4731(6) 0.076(8) Uiso 1 1 d . . . . .
H8A H -0.016(5) 0.570(5) 0.5488(7) 0.073(8) Uiso 1 1 d . . . . .
H8B H 0.170(5) 0.589(5) 0.5771(8) 0.086(9) Uiso 1 1 d . . . . .
H2 H 0.016(4) 0.754(4) 0.4937(5) 0.061(6) Uiso 1 1 d . . . . .
H1 H -0.197(4) 0.609(4) 0.3658(6) 0.056(7) Uiso 1 1 d . . . . .
H8C H 0.182(5) 0.785(5) 0.5483(7) 0.077(8) Uiso 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 O3 1.4236(17) . ?
S1 O1 1.5908(14) . ?
S1 N1 1.5986(18) . ?
S1 O2 1.4114(17) . ?
O1 C3 1.413(2) . ?
O5 C9 1.422(2) . ?
O5 H5 0.68(3) . ?
O4 C1 1.362(2) . ?
O4 C8 1.422(3) . ?
N1 C7 1.482(3) . ?
N1 H1 0.78(3) . ?
C7 C9 1.520(3) . ?
C7 C4 1.515(2) . ?
C7 H7 0.96(2) . ?
C9 H9A 0.96(3) . ?
C9 H9B 0.99(3) . ?
C2 C3 1.393(3) . ?
C2 C1 1.376(3) . ?
C2 H2 0.97(2) . ?
C4 C3 1.380(3) . ?
C4 C5 1.388(3) . ?
C1 C6 1.392(3) . ?
C5 C6 1.373(3) . ?
C5 H5A 0.97(3) . ?
C6 H6 0.96(3) . ?
C8 H8A 0.91(3) . ?
C8 H8B 1.07(3) . ?
C8 H8C 1.00(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
O3 S1 O1 106.53(9) . . ?
O3 S1 N1 108.22(10) . . ?
O1 S1 N1 104.61(9) . . ?
O2 S1 O3 120.36(12) . . ?
O2 S1 O1 105.47(9) . . ?
O2 S1 N1 110.44(11) . . ?
C3 O1 S1 116.27(11) . . ?
C9 O5 H5 111(3) . . ?
C1 O4 C8 118.2(2) . . ?
S1 N1 H1 110.1(18) . . ?
C7 N1 S1 116.61(13) . . ?
C7 N1 H1 117(2) . . ?
N1 C7 C9 110.30(17) . . ?
N1 C7 C4 112.70(16) . . ?
N1 C7 H7 100.6(13) . . ?
C9 C7 H7 110.0(13) . . ?
C4 C7 C9 112.96(16) . . ?
C4 C7 H7 109.6(12) . . ?
O5 C9 C7 110.75(17) . . ?
O5 C9 H9A 105.1(15) . . ?
O5 C9 H9B 111.9(13) . . ?
C7 C9 H9A 111.4(15) . . ?
C7 C9 H9B 110.9(14) . . ?
H9A C9 H9B 106.5(19) . . ?
C3 C2 H2 114.9(13) . . ?
C1 C2 C3 118.50(19) . . ?
C1 C2 H2 126.6(13) . . ?
C3 C4 C7 123.79(18) . . ?
C3 C4 C5 116.55(17) . . ?
C5 C4 C7 119.59(17) . . ?
C2 C3 O1 114.62(17) . . ?
C4 C3 O1 122.19(16) . . ?
C4 C3 C2 123.15(19) . . ?
O4 C1 C2 124.4(2) . . ?
O4 C1 C6 115.8(2) . . ?
C2 C1 C6 119.75(19) . . ?
C4 C5 H5A 119.3(14) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 H5A 118.5(14) . . ?
C1 C6 H6 119.1(14) . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 120.8(14) . . ?
O4 C8 H8A 111.6(17) . . ?
O4 C8 H8B 107.1(16) . . ?
O4 C8 H8C 109.3(17) . . ?
H8A C8 H8B 113(2) . . ?
H8A C8 H8C 102(3) . . ?
H8B C8 H8C 114(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.741
