# 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_exp_55
_database_code_depnum_ccdc_archive 'CCDC 1944189'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2019-09-14 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_audit_creation_date             2018-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 N O6 S'
_chemical_formula_sum            'C22 H17 N O6 S'
_chemical_formula_weight         423.43
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

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

_cell_length_a                   5.761
_cell_length_b                   15.96450(10)
_cell_length_c                   20.7087(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1904.61(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9480
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0360
_cell_measurement_theta_min      4.2450
_exptl_absorpt_coefficient_mu    1.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12830
_diffrn_reflns_theta_full        73.23
_diffrn_reflns_theta_max         73.23
_diffrn_reflns_theta_min         3.50
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  19.00   1.00    8.29    --  -41.12  37.00 -90.00   68
  2  ω   -114.00  -4.00   1.00    8.29    --  -41.12 -19.00  90.00  110
  3  ω    -98.00 -40.00   1.00    8.29    --  -41.12 -37.00  30.00   58
  4  ω     23.00  80.00   1.00    8.29    --   41.12-125.00   0.00   57
  5  ω     91.00 120.00   1.00    8.29    --   41.12-174.00-120.00   29
  6  ω     55.00 115.00   1.00   33.16    --  105.32-125.00  90.00   60
  7  ω     91.00 133.00   1.00   33.16    --  105.32  30.00-150.00   42
  8  ω    102.00 136.00   1.00   33.16    --  105.32 125.00-120.00   34
  9  ω     37.00 109.00   1.00   33.16    --  105.32 -94.00-180.00   72
 10  ω     94.00 173.00   1.00   33.16    --  105.32 125.00-150.00   79
 11  ω     79.00 178.00   1.00   33.16    --  105.32  45.00 -60.00   99
 12  ω    148.00 178.00   1.00   33.16    --  105.32  30.00-150.00   30
 13  ω     47.00 110.00   1.00   33.16    --  105.32-125.00-180.00   63
 14  ω     32.00 105.00   1.00   33.16    --  105.32 -94.00 -60.00   73
 15  ω    140.00 174.00   1.00   33.16    --  105.32 125.00   0.00   34
 16  ω     65.00 132.00   1.00   33.16    --  105.32 -30.00 120.00   67
 17  ω     32.00 133.00   1.00   33.16    --  105.32 -30.00 -90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1532025000
_diffrn_orient_matrix_UB_12      0.0671633000
_diffrn_orient_matrix_UB_13      0.0322082000
_diffrn_orient_matrix_UB_21      -0.0329076000
_diffrn_orient_matrix_UB_22      -0.0433369000
_diffrn_orient_matrix_UB_23      0.0658444000
_diffrn_orient_matrix_UB_31      0.2166678000
_diffrn_orient_matrix_UB_32      -0.0540631000
_diffrn_orient_matrix_UB_33      -0.0127700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3658
_reflns_number_total             3820
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.330(15)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0791
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C), C00U(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.75023(7) 0.41648(2) 0.462577(16) 0.03624(10) Uani 1 d . . .
O002 O 0.4196(3) 0.86296(8) 0.71515(6) 0.0531(3) Uani 1 d . . .
O003 O 1.0958(2) 0.72704(8) 0.80564(6) 0.0508(3) Uani 1 d . . .
O004 O 0.2251(2) 0.80590(8) 0.63274(6) 0.0545(3) Uani 1 d . . .
O005 O 0.6180(3) 0.42380(10) 0.40399(6) 0.0615(4) Uani 1 d . . .
N006 N 0.7253(2) 0.55575(7) 0.56868(6) 0.0364(3) Uani 1 d . . .
O9 O 0.8896(3) 0.34248(8) 0.46854(8) 0.0627(4) Uani 1 d . . .
O008 O 1.2129(3) 0.60092(10) 0.77038(7) 0.0664(4) Uani 1 d . . .
C009 C 0.8933(2) 0.56409(9) 0.52039(7) 0.0319(3) Uani 1 d . . .
C00A C 0.5664(3) 0.42254(9) 0.52912(7) 0.0321(3) Uani 1 d . . .
C00B C 0.8957(3) 0.66858(9) 0.71831(7) 0.0362(3) Uani 1 d . . .
C00C C 0.7263(3) 0.61639(9) 0.62050(7) 0.0358(3) Uani 1 d . . .
C00D C 0.5676(3) 0.73883(9) 0.67106(7) 0.0346(3) Uani 1 d . . .
C00E C 0.5743(3) 0.48749(9) 0.57447(7) 0.0315(3) Uani 1 d . . .
C00F C 0.9240(3) 0.50495(9) 0.47120(7) 0.0334(3) Uani 1 d . . .
C00G C 0.7342(3) 0.73342(9) 0.71924(7) 0.0358(3) Uani 1 d . . .
H00G H 0.7380 0.7731 0.7521 0.043 Uiso 1 calc . . R
C00H C 0.3842(3) 0.80529(10) 0.66977(8) 0.0392(3) Uani 1 d . . .
C00I C 1.0409(3) 0.63427(10) 0.51997(8) 0.0390(3) Uani 1 d . . .
H00I H 1.0234 0.6756 0.5513 0.047 Uiso 1 calc . . R
C00J C 0.5650(3) 0.68013(9) 0.62118(7) 0.0367(3) Uani 1 d . . .
H00J H 0.4548 0.6840 0.5885 0.044 Uiso 1 calc . . R
C00K C 1.0843(3) 0.66021(11) 0.76730(8) 0.0422(3) Uani 1 d . . .
C00L C 0.8892(3) 0.60956(9) 0.66911(8) 0.0368(3) Uani 1 d . . .
H00L H 0.9946 0.5654 0.6689 0.044 Uiso 1 calc . . R
C00M C 0.4235(3) 0.48165(10) 0.62773(8) 0.0411(3) Uani 1 d . . .
H00M H 0.4249 0.5233 0.6591 0.049 Uiso 1 calc . . R
C00N C 0.4136(3) 0.35535(10) 0.53633(8) 0.0424(3) Uani 1 d . . .
H00N H 0.4115 0.3129 0.5056 0.051 Uiso 1 calc . . R
C00O C 1.2431(3) 0.58277(11) 0.42620(8) 0.0494(4) Uani 1 d . . .
H00O H 1.3602 0.5889 0.3956 0.059 Uiso 1 calc . . R
C00P C 1.0987(3) 0.51427(11) 0.42501(8) 0.0445(4) Uani 1 d . . .
H00P H 1.1175 0.4738 0.3932 0.053 Uiso 1 calc . . R
C00Q C 1.2108(3) 0.64239(11) 0.47372(8) 0.0445(4) Uani 1 d . . .
H00Q H 1.3065 0.6893 0.4745 0.053 Uiso 1 calc . . R
C00R C 0.2666(4) 0.35143(10) 0.58836(9) 0.0497(4) Uani 1 d . . .
H00R H 0.1638 0.3069 0.5929 0.060 Uiso 1 calc . . R
C00S C 0.2737(3) 0.41466(10) 0.63392(8) 0.0467(4) Uani 1 d . . .
H00S H 0.1755 0.4120 0.6695 0.056 Uiso 1 calc . . R
C00T C 1.2736(4) 0.72504(16) 0.85456(9) 0.0641(5) Uani 1 d . . .
H00A H 1.4185 0.7087 0.8354 0.096 Uiso 1 calc . . GR
H00B H 1.2316 0.6854 0.8874 0.096 Uiso 1 calc . . GR
H00C H 1.2892 0.7797 0.8735 0.096 Uiso 1 calc . . GR
C00U C 0.2485(5) 0.92918(14) 0.71827(10) 0.0738(6) Uani 1 d . . .
H00D H 0.2280 0.9531 0.6761 0.111 Uiso 1 calc . . GR
H00E H 0.3003 0.9717 0.7477 0.111 Uiso 1 calc . . GR
H00F H 0.1034 0.9066 0.7331 0.111 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 O005 1.4372(14) . ?
S1 O9 1.4339(13) . ?
S1 C00A 1.7406(15) . ?
S1 C00F 1.7404(15) . ?
O002 C00H 1.331(2) . ?
O002 C00U 1.447(2) . ?
O003 C00K 1.331(2) . ?
O003 C00T 1.441(2) . ?
O004 C00H 1.195(2) . ?
N006 C009 1.3981(19) . ?
N006 C00C 1.4453(17) . ?
N006 C00E 1.3995(18) . ?
O008 C00K 1.204(2) . ?
C009 C00F 1.400(2) . ?
C009 C00I 1.406(2) . ?
C00A C00E 1.3997(19) . ?
C00A C00N 1.395(2) . ?
C00B C00G 1.392(2) . ?
C00B C00K 1.492(2) . ?
C00B C00L 1.388(2) . ?
C00C C00J 1.378(2) . ?
C00C C00L 1.381(2) . ?
C00D C00G 1.387(2) . ?
C00D C00H 1.498(2) . ?
C00D C00J 1.395(2) . ?
C00E C00M 1.407(2) . ?
C00F C00P 1.396(2) . ?
C00G H00G 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00Q 1.376(2) . ?
C00J H00J 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00S 1.380(2) . ?
C00N H00N 0.9300 . ?
C00N C00R 1.372(2) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.374(3) . ?
C00O C00Q 1.382(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00S 1.382(3) . ?
C00S H00S 0.9300 . ?
C00T H00A 0.9600 . ?
C00T H00B 0.9600 . ?
C00T H00C 0.9600 . ?
C00U H00D 0.9600 . ?
C00U H00E 0.9600 . ?
C00U H00F 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
O005 S1 C00A 109.95(8) . . ?
O005 S1 C00F 109.00(8) . . ?
O9 S1 O005 115.88(10) . . ?
O9 S1 C00A 108.57(8) . . ?
O9 S1 C00F 109.73(8) . . ?
C00F S1 C00A 102.93(7) . . ?
C00H O002 C00U 115.60(15) . . ?
C00K O003 C00T 115.90(15) . . ?
C009 N006 C00C 117.68(12) . . ?
C009 N006 C00E 124.45(11) . . ?
C00E N006 C00C 117.42(12) . . ?
N006 C009 C00F 122.94(12) . . ?
N006 C009 C00I 119.91(13) . . ?
C00F C009 C00I 117.15(14) . . ?
C00E C00A S1 123.54(11) . . ?
C00N C00A S1 115.19(11) . . ?
C00N C00A C00E 121.21(14) . . ?
C00G C00B C00K 122.93(13) . . ?
C00L C00B C00G 119.79(14) . . ?
C00L C00B C00K 117.25(14) . . ?
C00J C00C N006 119.97(14) . . ?
C00J C00C C00L 120.61(13) . . ?
C00L C00C N006 119.42(14) . . ?
C00G C00D C00H 123.04(13) . . ?
C00G C00D C00J 119.88(13) . . ?
C00J C00D C00H 117.08(14) . . ?
N006 C00E C00A 122.66(13) . . ?
N006 C00E C00M 120.15(13) . . ?
C00A C00E C00M 117.19(13) . . ?
C009 C00F S1 123.31(11) . . ?
C00P C00F S1 115.51(11) . . ?
C00P C00F C009 121.18(14) . . ?
C00B C00G H00G 120.0 . . ?
C00D C00G C00B 119.93(12) . . ?
C00D C00G H00G 120.0 . . ?
O002 C00H C00D 111.66(14) . . ?
O004 C00H O002 124.40(14) . . ?
O004 C00H C00D 123.94(14) . . ?
C009 C00I H00I 119.7 . . ?
C00Q C00I C009 120.62(15) . . ?
C00Q C00I H00I 119.7 . . ?
C00C C00J C00D 119.77(14) . . ?
C00C C00J H00J 120.1 . . ?
C00D C00J H00J 120.1 . . ?
O003 C00K C00B 111.71(14) . . ?
O008 C00K O003 124.59(16) . . ?
O008 C00K C00B 123.68(15) . . ?
C00B C00L H00L 120.0 . . ?
C00C C00L C00B 119.99(13) . . ?
C00C C00L H00L 120.0 . . ?
C00E C00M H00M 119.7 . . ?
C00S C00M C00E 120.67(15) . . ?
C00S C00M H00M 119.7 . . ?
C00A C00N H00N 119.7 . . ?
C00R C00N C00A 120.56(15) . . ?
C00R C00N H00N 119.7 . . ?
C00P C00O H00O 120.7 . . ?
C00P C00O C00Q 118.65(16) . . ?
C00Q C00O H00O 120.7 . . ?
C00F C00P H00P 119.7 . . ?
C00O C00P C00F 120.58(15) . . ?
C00O C00P H00P 119.7 . . ?
C00I C00Q C00O 121.79(15) . . ?
C00I C00Q H00Q 119.1 . . ?
C00O C00Q H00Q 119.1 . . ?
C00N C00R H00R 120.5 . . ?
C00N C00R C00S 118.97(15) . . ?
C00S C00R H00R 120.5 . . ?
C00M C00S C00R 121.40(15) . . ?
C00M C00S H00S 119.3 . . ?
C00R C00S H00S 119.3 . . ?
O003 C00T H00A 109.5 . . ?
O003 C00T H00B 109.5 . . ?
O003 C00T H00C 109.5 . . ?
H00A C00T H00B 109.5 . . ?
H00A C00T H00C 109.5 . . ?
H00B C00T H00C 109.5 . . ?
O002 C00U H00D 109.5 . . ?
O002 C00U H00E 109.5 . . ?
O002 C00U H00F 109.5 . . ?
H00D C00U H00E 109.5 . . ?
H00D C00U H00F 109.5 . . ?
H00E C00U H00F 109.5 . . ?

_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.903
####################################################################### 
# 
# 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_exp_61-2cooch3-no-ohua-zhenzhuang
_database_code_depnum_ccdc_archive 'CCDC 1963173'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_audit_creation_date             2019-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 N O4 S'
_chemical_formula_sum            'C22 H17 N O4 S'
_chemical_formula_weight         391.43
_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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
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+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'

_cell_length_a                   6.6807(2)
_cell_length_b                   19.9408(7)
_cell_length_c                   14.2683(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1900.80(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0010
_cell_measurement_theta_min      6.2070
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4351
_diffrn_reflns_theta_full        67.02
_diffrn_reflns_theta_max         67.02
_diffrn_reflns_theta_min         3.81
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -15.00   1.00    2.50    --  -41.12 -57.00  30.00   71
  2  ω      2.00  42.00   1.00    2.50    --   41.12 -99.00 120.00   40
  3  ω     47.00  85.00   1.00    2.50    --   41.12-125.00  90.00   38
  4  ω    135.00 173.00   1.00    9.98    --  105.32  45.00 -30.00   38
  5  ω     53.00  96.00   1.00    9.98    --  105.32-125.00  60.00   43
  6  ω    135.00 178.00   1.00    9.98    --  105.32 124.00  75.00   43
  7  ω     95.00 178.00   1.00    9.98    --  105.32 125.00 -90.00   83
  8  ω     97.00 178.00   1.00    9.98    --  105.32 125.00 -30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1865912000
_diffrn_orient_matrix_UB_12      0.0409908000
_diffrn_orient_matrix_UB_13      0.0272480000
_diffrn_orient_matrix_UB_21      -0.1345573000
_diffrn_orient_matrix_UB_22      -0.0605645000
_diffrn_orient_matrix_UB_23      -0.0233723000
_diffrn_orient_matrix_UB_31      0.0187116000
_diffrn_orient_matrix_UB_32      -0.0248970000
_diffrn_orient_matrix_UB_33      0.1017308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1554
_reflns_number_total             1741
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.074
_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)+(0.0764P)²+0.4142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1328
_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    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.93976(13) 0.2500 0.38849(6) 0.0853(4) Uani 1 d . . 2 S T P
O2 O 0.5128(2) 0.37134(6) 0.87447(8) 0.0512(4) Uani 1 d . . 1 . . .
O3 O 0.5641(3) 0.42852(6) 0.74244(10) 0.0702(5) Uani 1 d . . 1 . . .
N4 N 0.5521(3) 0.2500 0.48892(13) 0.0468(5) Uani 1 d . . 2 S T P
C5 C 0.5365(3) 0.2500 0.78551(15) 0.0348(4) Uani 1 d . . 2 S T P
C6 C 0.5416(2) 0.30948(7) 0.73547(10) 0.0356(4) Uani 1 d . . 1 . . .
C7 C 0.5481(3) 0.2500 0.58749(15) 0.0362(5) Uani 1 d . . 2 S T P
C8 C 0.5479(2) 0.30989(7) 0.63815(11) 0.0373(4) Uani 1 d . . 1 . . .
C9 C 0.5412(2) 0.37607(8) 0.78217(11) 0.0414(4) Uani 1 d . . 1 . . .
C10 C 0.5900(3) 0.31039(8) 0.43817(11) 0.0492(4) Uani 1 d . . 1 . . .
C11 C 0.4517(4) 0.36169(11) 0.43597(15) 0.0685(6) Uani 1 d . . 1 . . .
C12 C 0.7676(3) 0.31647(10) 0.38877(12) 0.0604(5) Uani 1 d . . 1 . . .
C13 C 0.4935(5) 0.43381(11) 0.92375(16) 0.0717(6) Uani 1 d . . 1 . . .
C14 C 0.4966(7) 0.42076(12) 0.38827(19) 0.0933(10) Uani 1 d . . 1 . . .
C15 C 0.8060(5) 0.37549(16) 0.33936(15) 0.0865(9) Uani 1 d . . 1 . . .
C16 C 0.6729(7) 0.42690(14) 0.34048(18) 0.1021(13) Uani 1 d . . 1 . . .
H8 H 0.553(3) 0.3498(10) 0.6077(13) 0.047(5) Uiso 1 d . . 1 . . .
H5 H 0.537(4) 0.2500 0.849(2) 0.056(8) Uiso 1 d . . 2 S T P
H13A H 0.634(5) 0.4552(16) 0.928(2) 0.096(9) Uiso 1 d . . 1 . . .
H11 H 0.327(4) 0.3549(13) 0.4667(17) 0.081(8) Uiso 1 d . . 1 . . .
H13B H 0.450(4) 0.4223(15) 0.985(2) 0.102(10) Uiso 1 d . . 1 . . .
H16 H 0.700(5) 0.4704(19) 0.309(2) 0.131(11) Uiso 1 d . . 1 . . .
H14 H 0.393(5) 0.4584(18) 0.388(2) 0.119(11) Uiso 1 d . . 1 . . .
H13C H 0.410(5) 0.4659(17) 0.889(2) 0.107(10) Uiso 1 d . . 1 . . .
H15 H 0.928(5) 0.3743(18) 0.305(3) 0.121(12) Uiso 1 d . . 1 . . .


_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 C12 1.755(2) 8_565 ?
S1 C12 1.755(2) . ?
O2 C9 1.334(2) . ?
O2 C13 1.436(2) . ?
O3 C9 1.200(2) . ?
N4 C7 1.407(3) . ?
N4 C10 1.4278(18) . ?
N4 C10 1.4278(18) 8_565 ?
C5 C6 1.3848(18) 8_565 ?
C5 C6 1.3848(18) . ?
C6 C8 1.389(2) . ?
C6 C9 1.486(2) . ?
C7 C8 1.3960(18) . ?
C7 C8 1.3960(18) 8_565 ?
C10 C11 1.379(3) . ?
C10 C12 1.385(3) . ?
C11 C14 1.393(4) . ?
C12 C15 1.396(3) . ?
C14 C16 1.366(5) . ?
C15 C16 1.357(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C12 98.10(13) 8_565 . ?
C9 O2 C13 115.78(14) . . ?
C7 N4 C10 120.70(10) . . ?
C7 N4 C10 120.70(10) . 8_565 ?
C10 N4 C10 115.00(18) 8_565 . ?
C6 C5 C6 117.85(18) 8_565 . ?
C5 C6 C8 121.41(13) . . ?
C5 C6 C9 122.29(14) . . ?
C8 C6 C9 116.30(13) . . ?
C8 C7 N4 121.18(10) 8_565 . ?
C8 C7 N4 121.18(10) . . ?
C8 C7 C8 117.62(19) . 8_565 ?
C6 C8 C7 120.84(14) . . ?
O2 C9 C6 112.33(13) . . ?
O3 C9 O2 123.11(14) . . ?
O3 C9 C6 124.55(14) . . ?
C11 C10 N4 121.23(19) . . ?
C11 C10 C12 119.82(19) . . ?
C12 C10 N4 118.94(17) . . ?
C10 C11 C14 119.6(3) . . ?
C10 C12 S1 119.75(14) . . ?
C10 C12 C15 119.2(2) . . ?
C15 C12 S1 121.0(2) . . ?
C16 C14 C11 120.3(3) . . ?
C16 C15 C12 120.7(3) . . ?
C15 C16 C14 120.2(2) . . ?

_olex2_date_sample_data_collection 2019-01-07
_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 1.485
_oxdiff_exptl_absorpt_empirical_full_min 0.700
