# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 2060837'
loop_
_audit_author_name
_audit_author_address
'Gangguo Zhu'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C21 H19 N O3 S)'
_chemical_formula_sum            'C5.25 H4.75 N0.25 O0.75 S0.25'
_chemical_formula_weight         91.36
_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                   5.8167(2)
_cell_length_b                   17.2043(6)
_cell_length_c                   19.0214(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.831(2)
_cell_angle_gamma                90
_cell_volume                     1902.54(12)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9554
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0756 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9264.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19469
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.368
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3717
_reflns_number_total             4289
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.115
_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)+(0.0899P)²+0.3573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1580
_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:
 C008(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C00O(H00O), C00Q(H00S)
2.c Idealised Me refined as rotating group:
 C00M(H00C,H00E,H00G), C00N(H00M,H00N,H00I), C00P(H00P,H00Q,H00R)
;
_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
S001 S 0.73586(7) 0.30489(2) 0.80485(2) 0.05064(17) Uani 1 1 d . . . . .
O002 O 0.7352(3) 0.36298(8) 0.75112(7) 0.0691(4) Uani 1 1 d . . . . .
O003 O 0.9496(2) 0.27022(10) 0.82777(9) 0.0721(4) Uani 1 1 d . . . . .
C004 C 0.5526(3) 0.22799(8) 0.77777(8) 0.0423(3) Uani 1 1 d . . . . .
N005 N 0.2412(4) 0.47551(11) 0.44394(9) 0.0714(5) Uani 1 1 d . . . . .
C006 C 0.5960(3) 0.34155(9) 0.87855(9) 0.0472(4) Uani 1 1 d . . . . .
C007 C 0.4242(3) 0.22466(9) 0.71840(8) 0.0444(3) Uani 1 1 d . . . . .
C008 C 0.5255(3) 0.15948(10) 0.82576(9) 0.0536(4) Uani 1 1 d . . . . .
H00A H 0.449926 0.174845 0.868928 0.064 Uiso 1 1 calc R . . . .
H00B H 0.675320 0.136422 0.838336 0.064 Uiso 1 1 calc R . . . .
C009 C 0.3931(3) 0.27940(9) 0.65890(8) 0.0436(3) Uani 1 1 d . . . . .
C00A C 0.3759(3) 0.10236(9) 0.78296(10) 0.0512(4) Uani 1 1 d . . . . .
O00B O 0.1322(4) 0.13404(12) 0.68055(10) 0.1115(8) Uani 1 1 d . . . . .
C00C C 0.3169(3) 0.37943(9) 0.54637(8) 0.0472(4) Uani 1 1 d . . . . .
C00D C 0.5548(3) 0.28616(11) 0.60726(10) 0.0552(4) Uani 1 1 d . . . . .
H00D H 0.690722 0.256637 0.610511 0.066 Uiso 1 1 calc R . . . .
C00E C 0.2767(3) 0.43298(10) 0.48894(9) 0.0551(4) Uani 1 1 d . . . . .
C00F C 0.1922(3) 0.32244(11) 0.65296(10) 0.0561(4) Uani 1 1 d . . . . .
H00F H 0.080215 0.317385 0.687234 0.067 Uiso 1 1 calc R . . . .
C00G C 0.3613(3) 0.39708(12) 0.99292(10) 0.0608(5) Uani 1 1 d . . . . .
C00H C 0.1547(3) 0.37279(11) 0.59708(10) 0.0557(4) Uani 1 1 d . . . . .
H00H H 0.018871 0.402361 0.593758 0.067 Uiso 1 1 calc R . . . .
C00I C 0.2876(4) 0.15081(11) 0.72113(10) 0.0605(5) Uani 1 1 d . . . . .
C00J C 0.5178(3) 0.33587(12) 0.55117(10) 0.0581(4) Uani 1 1 d . . . . .
H00J H 0.628119 0.340262 0.516337 0.070 Uiso 1 1 calc R . . . .
C00K C 0.6649(3) 0.32013(12) 0.94531(10) 0.0605(5) Uani 1 1 d . . . . .
H00K H 0.790876 0.286511 0.952431 0.073 Uiso 1 1 calc R . . . .
C00L C 0.4095(4) 0.39001(14) 0.86736(11) 0.0720(6) Uani 1 1 d . . . . .
H00L H 0.361433 0.404123 0.821470 0.086 Uiso 1 1 calc R . . . .
C00M C 0.1782(4) 0.06995(14) 0.82450(14) 0.0775(7) Uani 1 1 d . . . . .
H00C H 0.239338 0.040643 0.864451 0.116 Uiso 1 1 calc GR . . . .
H00E H 0.084714 0.036093 0.794499 0.116 Uiso 1 1 calc GR . . . .
H00G H 0.084621 0.112452 0.841026 0.116 Uiso 1 1 calc GR . . . .
C00N C 0.5234(4) 0.03681(13) 0.75411(13) 0.0763(6) Uani 1 1 d . . . . .
H00M H 0.651368 0.058868 0.729427 0.114 Uiso 1 1 calc GR . . . .
H00N H 0.430728 0.005177 0.721913 0.114 Uiso 1 1 calc GR . . . .
H00I H 0.581676 0.004826 0.792713 0.114 Uiso 1 1 calc GR . . . .
C00O C 0.5483(4) 0.34818(13) 1.00208(10) 0.0650(5) Uani 1 1 d . . . . .
H00O H 0.597036 0.333744 1.047833 0.078 Uiso 1 1 calc R . . . .
C00P C 0.2334(5) 0.42718(18) 1.05469(13) 0.0851(7) Uani 1 1 d . . . . .
H00P H 0.301485 0.406065 1.097814 0.128 Uiso 1 1 calc GR . . . .
H00Q H 0.073477 0.411456 1.050261 0.128 Uiso 1 1 calc GR . . . .
H00R H 0.242778 0.483462 1.055862 0.128 Uiso 1 1 calc GR . . . .
C00Q C 0.2946(4) 0.41746(16) 0.92474(12) 0.0813(7) Uani 1 1 d . . . . .
H00S H 0.168024 0.450782 0.917392 0.098 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
S001 O002 1.4293(15) . ?
S001 O003 1.4344(15) . ?
S001 C004 1.7655(16) . ?
S001 C006 1.7600(17) . ?
C004 C007 1.335(2) . ?
C004 C008 1.502(2) . ?
N005 C00E 1.140(2) . ?
C006 C00K 1.370(2) . ?
C006 C00L 1.379(3) . ?
C007 C009 1.479(2) . ?
C007 C00I 1.500(2) . ?
C008 H00A 0.9800 . ?
C008 H00B 0.9800 . ?
C008 C00A 1.530(2) . ?
C009 C00D 1.387(2) . ?
C009 C00F 1.385(2) . ?
C00A C00I 1.517(2) . ?
C00A C00M 1.521(3) . ?
C00A C00N 1.529(3) . ?
O00B C00I 1.205(2) . ?
C00C C00E 1.442(2) . ?
C00C C00H 1.376(3) . ?
C00C C00J 1.389(3) . ?
C00D H00D 0.9400 . ?
C00D C00J 1.379(2) . ?
C00F H00F 0.9400 . ?
C00F C00H 1.383(2) . ?
C00G C00O 1.382(3) . ?
C00G C00P 1.503(3) . ?
C00G C00Q 1.387(3) . ?
C00H H00H 0.9400 . ?
C00J H00J 0.9400 . ?
C00K H00K 0.9400 . ?
C00K C00O 1.380(3) . ?
C00L H00L 0.9400 . ?
C00L C00Q 1.381(3) . ?
C00M H00C 0.9700 . ?
C00M H00E 0.9700 . ?
C00M H00G 0.9700 . ?
C00N H00M 0.9700 . ?
C00N H00N 0.9700 . ?
C00N H00I 0.9700 . ?
C00O H00O 0.9400 . ?
C00P H00P 0.9700 . ?
C00P H00Q 0.9700 . ?
C00P H00R 0.9700 . ?
C00Q H00S 0.9400 . ?

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
O002 S001 O003 119.37(10) . . ?
O002 S001 C004 109.12(8) . . ?
O002 S001 C006 109.16(8) . . ?
O003 S001 C004 106.64(8) . . ?
O003 S001 C006 108.99(9) . . ?
C006 S001 C004 102.17(8) . . ?
C007 C004 S001 126.52(12) . . ?
C007 C004 C008 114.44(14) . . ?
C008 C004 S001 119.00(12) . . ?
C00K C006 S001 120.86(13) . . ?
C00K C006 C00L 120.73(17) . . ?
C00L C006 S001 118.37(14) . . ?
C004 C007 C009 132.18(14) . . ?
C004 C007 C00I 106.83(14) . . ?
C009 C007 C00I 120.91(14) . . ?
C004 C008 H00A 110.9 . . ?
C004 C008 H00B 110.9 . . ?
C004 C008 C00A 104.44(13) . . ?
H00A C008 H00B 108.9 . . ?
C00A C008 H00A 110.9 . . ?
C00A C008 H00B 110.9 . . ?
C00D C009 C007 121.74(15) . . ?
C00F C009 C007 119.03(15) . . ?
C00F C009 C00D 119.16(15) . . ?
C00I C00A C008 103.42(13) . . ?
C00I C00A C00M 111.19(16) . . ?
C00I C00A C00N 107.87(17) . . ?
C00M C00A C008 112.67(17) . . ?
C00M C00A C00N 110.98(17) . . ?
C00N C00A C008 110.37(16) . . ?
C00H C00C C00E 119.06(16) . . ?
C00H C00C C00J 120.25(15) . . ?
C00J C00C C00E 120.68(16) . . ?
C009 C00D H00D 119.8 . . ?
C00J C00D C009 120.49(16) . . ?
C00J C00D H00D 119.8 . . ?
N005 C00E C00C 178.8(2) . . ?
C009 C00F H00F 119.7 . . ?
C00H C00F C009 120.62(16) . . ?
C00H C00F H00F 119.7 . . ?
C00O C00G C00P 121.24(19) . . ?
C00O C00G C00Q 117.87(18) . . ?
C00Q C00G C00P 120.9(2) . . ?
C00C C00H C00F 119.74(16) . . ?
C00C C00H H00H 120.1 . . ?
C00F C00H H00H 120.1 . . ?
C007 C00I C00A 109.01(14) . . ?
O00B C00I C007 124.60(17) . . ?
O00B C00I C00A 126.38(17) . . ?
C00C C00J H00J 120.1 . . ?
C00D C00J C00C 119.72(16) . . ?
C00D C00J H00J 120.1 . . ?
C006 C00K H00K 120.2 . . ?
C006 C00K C00O 119.64(17) . . ?
C00O C00K H00K 120.2 . . ?
C006 C00L H00L 120.6 . . ?
C006 C00L C00Q 118.88(18) . . ?
C00Q C00L H00L 120.6 . . ?
C00A C00M H00C 109.5 . . ?
C00A C00M H00E 109.5 . . ?
C00A C00M H00G 109.5 . . ?
H00C C00M H00E 109.5 . . ?
H00C C00M H00G 109.5 . . ?
H00E C00M H00G 109.5 . . ?
C00A C00N H00M 109.5 . . ?
C00A C00N H00N 109.5 . . ?
C00A C00N H00I 109.5 . . ?
H00M C00N H00N 109.5 . . ?
H00M C00N H00I 109.5 . . ?
H00N C00N H00I 109.5 . . ?
C00G C00O H00O 119.4 . . ?
C00K C00O C00G 121.24(18) . . ?
C00K C00O H00O 119.4 . . ?
C00G C00P H00P 109.5 . . ?
C00G C00P H00Q 109.5 . . ?
C00G C00P H00R 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
H00P C00P H00R 109.5 . . ?
H00Q C00P H00R 109.5 . . ?
C00G C00Q H00S 119.2 . . ?
C00L C00Q C00G 121.64(19) . . ?
C00L C00Q H00S 119.2 . . ?

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
S001 C004 C007 C009 0.4(3) . . . . ?
S001 C004 C007 C00I -176.39(13) . . . . ?
S001 C004 C008 C00A -174.85(12) . . . . ?
S001 C006 C00K C00O -178.32(17) . . . . ?
S001 C006 C00L C00Q 178.3(2) . . . . ?
O002 S001 C004 C007 -2.78(18) . . . . ?
O002 S001 C004 C008 179.81(13) . . . . ?
O002 S001 C006 C00K -146.55(16) . . . . ?
O002 S001 C006 C00L 35.93(19) . . . . ?
O003 S001 C004 C007 -132.98(15) . . . . ?
O003 S001 C004 C008 49.61(15) . . . . ?
O003 S001 C006 C00K -14.58(19) . . . . ?
O003 S001 C006 C00L 167.90(17) . . . . ?
C004 S001 C006 C00K 98.00(17) . . . . ?
C004 S001 C006 C00L -79.52(18) . . . . ?
C004 C007 C009 C00D 77.9(2) . . . . ?
C004 C007 C009 C00F -105.0(2) . . . . ?
C004 C007 C00I C00A -9.5(2) . . . . ?
C004 C007 C00I O00B 169.9(2) . . . . ?
C004 C008 C00A C00I -12.26(19) . . . . ?
C004 C008 C00A C00M -132.42(16) . . . . ?
C004 C008 C00A C00N 102.90(18) . . . . ?
C006 S001 C004 C007 112.70(15) . . . . ?
C006 S001 C004 C008 -64.71(14) . . . . ?
C006 C00K C00O C00G 0.6(3) . . . . ?
C006 C00L C00Q C00G -0.4(4) . . . . ?
C007 C004 C008 C00A 7.4(2) . . . . ?
C007 C009 C00D C00J 177.91(17) . . . . ?
C007 C009 C00F C00H -178.42(17) . . . . ?
C008 C004 C007 C009 177.86(17) . . . . ?
C008 C004 C007 C00I 1.1(2) . . . . ?
C008 C00A C00I C007 13.6(2) . . . . ?
C008 C00A C00I O00B -165.9(3) . . . . ?
C009 C007 C00I C00A 173.29(15) . . . . ?
C009 C007 C00I O00B -7.2(3) . . . . ?
C009 C00D C00J C00C -0.1(3) . . . . ?
C009 C00F C00H C00C 0.9(3) . . . . ?
C00D C009 C00F C00H -1.3(3) . . . . ?
C00E C00C C00H C00F -179.16(17) . . . . ?
C00E C00C C00J C00D 178.72(18) . . . . ?
C00F C009 C00D C00J 0.9(3) . . . . ?
C00H C00C C00J C00D -0.4(3) . . . . ?
C00I C007 C009 C00D -105.7(2) . . . . ?
C00I C007 C009 C00F 71.3(2) . . . . ?
C00J C00C C00H C00F -0.1(3) . . . . ?
C00K C006 C00L C00Q 0.8(4) . . . . ?
C00L C006 C00K C00O -0.9(3) . . . . ?
C00M C00A C00I C007 134.73(19) . . . . ?
C00M C00A C00I O00B -44.7(3) . . . . ?
C00N C00A C00I C007 -103.38(18) . . . . ?
C00N C00A C00I O00B 77.2(3) . . . . ?
C00O C00G C00Q C00L 0.2(4) . . . . ?
C00P C00G C00O C00K 179.6(2) . . . . ?
C00P C00G C00Q C00L -179.7(3) . . . . ?
C00Q C00G C00O C00K -0.3(4) . . . . ?

_shelx_SHELXL_version_number     2017/1

_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_a_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2060838'
loop_
_audit_author_name
_audit_author_address
'Gangguo Zhu'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O4 S'
_chemical_formula_sum            'C20 H20 O4 S'
_chemical_formula_weight         356.42
_chemical_absolute_configuration ?
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8083(4)
_cell_length_b                   11.6866(6)
_cell_length_c                   14.3467(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1812.16(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8093
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.450
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6836
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.9168.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15036
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.359
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3815
_reflns_number_total             4091
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 
;
 Flack x determined using 1546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.151
_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)+(0.0568P)²+0.0850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0977
_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:
 C00A(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00H(H00J), C00I(H00K), C00J(H00L), C00K(H00M), C00L(H00N),
 C00N(H00R), C00O(H00S), C00P(H00T)
2.c Idealised Me refined as rotating group:
 C00F(H00F,H00D,H00E), C00G(H00G,H00H,H00I), C00M(H00O,H00P,H00Q)
;
_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
S001 S 0.44049(5) 0.51546(5) 0.75389(4) 0.04324(16) Uani 1 1 d . . . . .
O002 O 0.80805(15) 0.42535(16) 0.61397(11) 0.0535(4) Uani 1 1 d . . . . .
O003 O 0.44321(17) 0.44805(16) 0.83749(11) 0.0572(4) Uani 1 1 d . . . . .
O004 O 0.42352(18) 0.63684(14) 0.76177(12) 0.0565(4) Uani 1 1 d . . . . .
O005 O 0.73956(16) 0.48536(18) 0.47918(11) 0.0561(4) Uani 1 1 d . . . . .
C006 C 0.51858(19) 0.5816(2) 0.54532(15) 0.0424(5) Uani 1 1 d . . . . .
C007 C 0.3269(2) 0.45829(19) 0.68021(16) 0.0434(5) Uani 1 1 d . . . . .
C008 C 0.8068(2) 0.4343(2) 0.71662(16) 0.0486(5) Uani 1 1 d . . . . .
C009 C 0.60531(18) 0.51793(18) 0.60715(14) 0.0387(4) Uani 1 1 d . . . . .
C00A C 0.6756(2) 0.4197(2) 0.75186(16) 0.0473(5) Uani 1 1 d . . . . .
H00A H 0.6531 0.3385 0.7494 0.057 Uiso 1 1 calc R . . . .
H00B H 0.6713 0.4444 0.8171 0.057 Uiso 1 1 calc R . . . .
C00B C 0.2387(2) 0.5281(2) 0.63938(17) 0.0509(5) Uani 1 1 d . . . . .
H00C H 0.2382 0.6072 0.6514 0.061 Uiso 1 1 calc R . . . .
C00C C 0.72253(19) 0.4773(2) 0.56210(15) 0.0423(4) Uani 1 1 d . . . . .
C00D C 0.58455(18) 0.48719(19) 0.69560(13) 0.0393(4) Uani 1 1 d . . . . .
C00E C 0.1518(2) 0.3638(2) 0.56100(17) 0.0520(6) Uani 1 1 d . . . . .
C00F C 0.8872(3) 0.3356(3) 0.7488(2) 0.0709(8) Uani 1 1 d . . . . .
H00F H 0.8559 0.2646 0.7228 0.106 Uiso 1 1 calc GR . . . .
H00D H 0.8857 0.3312 0.8163 0.106 Uiso 1 1 calc GR . . . .
H00E H 0.9715 0.3477 0.7278 0.106 Uiso 1 1 calc GR . . . .
C00G C 0.8616(3) 0.5480(3) 0.74291(19) 0.0639(7) Uani 1 1 d . . . . .
H00G H 0.9408 0.5575 0.7120 0.096 Uiso 1 1 calc GR . . . .
H00H H 0.8733 0.5512 0.8099 0.096 Uiso 1 1 calc GR . . . .
H00I H 0.8061 0.6089 0.7238 0.096 Uiso 1 1 calc GR . . . .
C00H C 0.3285(2) 0.3412(2) 0.66308(18) 0.0522(6) Uani 1 1 d . . . . .
H00J H 0.3874 0.2938 0.6920 0.063 Uiso 1 1 calc R . . . .
C00I C 0.1514(2) 0.4801(3) 0.58073(18) 0.0558(6) Uani 1 1 d . . . . .
H00K H 0.0906 0.5272 0.5537 0.067 Uiso 1 1 calc R . . . .
C00J C 0.4573(2) 0.5234(2) 0.47457(16) 0.0536(6) Uani 1 1 d . . . . .
H00L H 0.4741 0.4456 0.4639 0.064 Uiso 1 1 calc R . . . .
C00K C 0.4977(2) 0.6970(2) 0.5589(2) 0.0559(6) Uani 1 1 d . . . . .
H00M H 0.5403 0.7367 0.6060 0.067 Uiso 1 1 calc R . . . .
C00L C 0.2423(2) 0.2961(2) 0.60289(19) 0.0559(6) Uani 1 1 d . . . . .
H00N H 0.2444 0.2174 0.5896 0.067 Uiso 1 1 calc R . . . .
C00M C 0.0582(3) 0.3124(3) 0.4967(2) 0.0723(8) Uani 1 1 d . . . . .
H00O H 0.0089 0.3728 0.4689 0.108 Uiso 1 1 calc GR . . . .
H00P H 0.0047 0.2612 0.5315 0.108 Uiso 1 1 calc GR . . . .
H00Q H 0.1002 0.2699 0.4480 0.108 Uiso 1 1 calc GR . . . .
C00N C 0.3715(3) 0.5803(4) 0.41965(19) 0.0714(9) Uani 1 1 d . . . . .
H00R H 0.3285 0.5408 0.3726 0.086 Uiso 1 1 calc R . . . .
C00O C 0.3497(3) 0.6953(4) 0.4345(2) 0.0838(11) Uani 1 1 d . . . . .
H00S H 0.2910 0.7339 0.3978 0.101 Uiso 1 1 calc R . . . .
C00P C 0.4133(3) 0.7539(3) 0.5026(3) 0.0761(9) Uani 1 1 d . . . . .
H00T H 0.3996 0.8326 0.5110 0.091 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
S001 O003 1.4353(17) . ?
S001 O004 1.4349(18) . ?
S001 C007 1.753(2) . ?
S001 C00D 1.798(2) . ?
O002 C008 1.476(3) . ?
O002 C00C 1.333(3) . ?
O005 C00C 1.207(3) . ?
C006 C009 1.489(3) . ?
C006 C00J 1.389(3) . ?
C006 C00K 1.382(4) . ?
C007 C00B 1.385(3) . ?
C007 C00H 1.391(3) . ?
C008 C00A 1.516(3) . ?
C008 C00F 1.516(4) . ?
C008 C00G 1.503(4) . ?
C009 C00C 1.499(3) . ?
C009 C00D 1.338(3) . ?
C00A H00A 0.9800 . ?
C00A H00B 0.9800 . ?
C00A C00D 1.497(3) . ?
C00B H00C 0.9400 . ?
C00B C00I 1.383(4) . ?
C00E C00I 1.389(4) . ?
C00E C00L 1.394(4) . ?
C00E C00M 1.495(4) . ?
C00F H00F 0.9700 . ?
C00F H00D 0.9700 . ?
C00F H00E 0.9700 . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?
C00G H00I 0.9700 . ?
C00H H00J 0.9400 . ?
C00H C00L 1.376(4) . ?
C00I H00K 0.9400 . ?
C00J H00L 0.9400 . ?
C00J C00N 1.386(4) . ?
C00K H00M 0.9400 . ?
C00K C00P 1.388(4) . ?
C00L H00N 0.9400 . ?
C00M H00O 0.9700 . ?
C00M H00P 0.9700 . ?
C00M H00Q 0.9700 . ?
C00N H00R 0.9400 . ?
C00N C00O 1.381(5) . ?
C00O H00S 0.9400 . ?
C00O C00P 1.378(5) . ?
C00P H00T 0.9400 . ?

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
O003 S001 C007 108.01(11) . . ?
O003 S001 C00D 105.67(10) . . ?
O004 S001 O003 118.64(11) . . ?
O004 S001 C007 109.56(11) . . ?
O004 S001 C00D 109.21(11) . . ?
C007 S001 C00D 104.84(10) . . ?
C00C O002 C008 121.21(18) . . ?
C00J C006 C009 119.4(2) . . ?
C00K C006 C009 120.4(2) . . ?
C00K C006 C00J 120.2(2) . . ?
C00B C007 S001 120.86(18) . . ?
C00B C007 C00H 120.9(2) . . ?
C00H C007 S001 118.21(18) . . ?
O002 C008 C00A 109.47(18) . . ?
O002 C008 C00F 104.1(2) . . ?
O002 C008 C00G 108.0(2) . . ?
C00A C008 C00F 110.4(2) . . ?
C00G C008 C00A 112.6(2) . . ?
C00G C008 C00F 111.8(2) . . ?
C006 C009 C00C 115.66(18) . . ?
C00D C009 C006 126.40(19) . . ?
C00D C009 C00C 117.75(19) . . ?
C008 C00A H00A 109.2 . . ?
C008 C00A H00B 109.2 . . ?
H00A C00A H00B 107.9 . . ?
C00D C00A C008 112.06(18) . . ?
C00D C00A H00A 109.2 . . ?
C00D C00A H00B 109.2 . . ?
C007 C00B H00C 120.4 . . ?
C00I C00B C007 119.2(2) . . ?
C00I C00B H00C 120.4 . . ?
O002 C00C C009 119.30(18) . . ?
O005 C00C O002 118.7(2) . . ?
O005 C00C C009 121.9(2) . . ?
C009 C00D S001 122.48(17) . . ?
C009 C00D C00A 122.87(19) . . ?
C00A C00D S001 114.52(15) . . ?
C00I C00E C00L 118.0(2) . . ?
C00I C00E C00M 121.1(3) . . ?
C00L C00E C00M 120.9(3) . . ?
C008 C00F H00F 109.5 . . ?
C008 C00F H00D 109.5 . . ?
C008 C00F H00E 109.5 . . ?
H00F C00F H00D 109.5 . . ?
H00F C00F H00E 109.5 . . ?
H00D C00F H00E 109.5 . . ?
C008 C00G H00G 109.5 . . ?
C008 C00G H00H 109.5 . . ?
C008 C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
C007 C00H H00J 120.7 . . ?
C00L C00H C007 118.6(2) . . ?
C00L C00H H00J 120.7 . . ?
C00B C00I C00E 121.2(2) . . ?
C00B C00I H00K 119.4 . . ?
C00E C00I H00K 119.4 . . ?
C006 C00J H00L 120.0 . . ?
C00N C00J C006 120.0(3) . . ?
C00N C00J H00L 120.0 . . ?
C006 C00K H00M 120.2 . . ?
C006 C00K C00P 119.5(3) . . ?
C00P C00K H00M 120.2 . . ?
C00E C00L H00N 119.0 . . ?
C00H C00L C00E 122.0(2) . . ?
C00H C00L H00N 119.0 . . ?
C00E C00M H00O 109.5 . . ?
C00E C00M H00P 109.5 . . ?
C00E C00M H00Q 109.5 . . ?
H00O C00M H00P 109.5 . . ?
H00O C00M H00Q 109.5 . . ?
H00P C00M H00Q 109.5 . . ?
C00J C00N H00R 120.2 . . ?
C00O C00N C00J 119.5(3) . . ?
C00O C00N H00R 120.2 . . ?
C00N C00O H00S 119.7 . . ?
C00P C00O C00N 120.5(3) . . ?
C00P C00O H00S 119.7 . . ?
C00K C00P H00T 119.9 . . ?
C00O C00P C00K 120.2(3) . . ?
C00O C00P H00T 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
S001 C007 C00B C00I 179.22(18) . . . . ?
S001 C007 C00H C00L -177.86(19) . . . . ?
O002 C008 C00A C00D -44.8(3) . . . . ?
O003 S001 C007 C00B 130.70(19) . . . . ?
O003 S001 C007 C00H -50.0(2) . . . . ?
O003 S001 C00D C009 167.06(18) . . . . ?
O003 S001 C00D C00A -8.96(19) . . . . ?
O004 S001 C007 C00B 0.1(2) . . . . ?
O004 S001 C007 C00H 179.45(18) . . . . ?
O004 S001 C00D C009 -64.3(2) . . . . ?
O004 S001 C00D C00A 119.72(17) . . . . ?
C006 C009 C00C O002 176.3(2) . . . . ?
C006 C009 C00C O005 -7.4(3) . . . . ?
C006 C009 C00D S001 2.2(3) . . . . ?
C006 C009 C00D C00A 177.9(2) . . . . ?
C006 C00J C00N C00O 1.5(4) . . . . ?
C006 C00K C00P C00O 0.9(4) . . . . ?
C007 S001 C00D C009 53.1(2) . . . . ?
C007 S001 C00D C00A -122.94(17) . . . . ?
C007 C00B C00I C00E -1.0(4) . . . . ?
C007 C00H C00L C00E -1.8(4) . . . . ?
C008 O002 C00C O005 166.6(2) . . . . ?
C008 O002 C00C C009 -16.9(3) . . . . ?
C008 C00A C00D S001 -159.36(17) . . . . ?
C008 C00A C00D C009 24.6(3) . . . . ?
C009 C006 C00J C00N 176.6(2) . . . . ?
C009 C006 C00K C00P -177.8(2) . . . . ?
C00B C007 C00H C00L 1.5(4) . . . . ?
C00C O002 C008 C00A 43.6(3) . . . . ?
C00C O002 C008 C00F 161.7(2) . . . . ?
C00C O002 C008 C00G -79.4(3) . . . . ?
C00C C009 C00D S001 -172.62(16) . . . . ?
C00C C009 C00D C00A 3.1(3) . . . . ?
C00D S001 C007 C00B -117.0(2) . . . . ?
C00D S001 C007 C00H 62.36(19) . . . . ?
C00D C009 C00C O002 -8.4(3) . . . . ?
C00D C009 C00C O005 168.0(2) . . . . ?
C00F C008 C00A C00D -158.9(2) . . . . ?
C00G C008 C00A C00D 75.3(3) . . . . ?
C00H C007 C00B C00I -0.1(4) . . . . ?
C00I C00E C00L C00H 0.8(4) . . . . ?
C00J C006 C009 C00C 69.1(3) . . . . ?
C00J C006 C009 C00D -105.8(3) . . . . ?
C00J C006 C00K C00P 1.2(4) . . . . ?
C00J C00N C00O C00P 0.6(5) . . . . ?
C00K C006 C009 C00C -111.8(2) . . . . ?
C00K C006 C009 C00D 73.3(3) . . . . ?
C00K C006 C00J C00N -2.4(4) . . . . ?
C00L C00E C00I C00B 0.7(4) . . . . ?
C00M C00E C00I C00B -179.3(2) . . . . ?
C00M C00E C00L C00H -179.3(2) . . . . ?
C00N C00O C00P C00K -1.8(5) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
