# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_dongmd_1208
_database_code_depnum_ccdc_archive 'CCDC 2114888'
loop_
_audit_author_name
_audit_author_address
'Jing Qi'
;Hebei University
China
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_audit_creation_date             2020-12-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 N O7 S'
_chemical_formula_sum            'C24 H25 N O7 S'
_chemical_formula_weight         471.51
_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 0.0181 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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.32517(16)
_cell_length_b                   11.40245(17)
_cell_length_c                   22.4950(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2391.89(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5826
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9900
_cell_measurement_theta_min      1.9990
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8276
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.973
_diffrn_reflns_theta_min         3.930
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  11.00   0.50    0.05    --   43.05 -19.00  90.00   84
  2  ω     35.00  60.00   0.50    0.05    --  109.26 -61.00 150.00   50
  3  ω    127.00 158.00   0.50    0.05    --  109.26  79.00  57.00   62
  4  ω     67.00 103.00   0.50    0.05    --  109.26 -77.00-180.00   72
  5  ω    -29.00  23.00   0.50    0.05    --   43.05 -19.00 -60.00  104
  6  ω     -1.00  26.00   0.50    0.05    --  -43.05  19.00-150.00   54
  7  ω    -53.00 -24.00   0.50    0.05    -- -100.00  45.00-133.00   58
  8  ω    -73.00 -26.00   0.50    0.05    -- -100.00  61.00 -90.00   94
  9  ω    -52.00 -27.00   0.50    0.05    -- -100.00  45.00 -30.00   50
 10  ω    -61.00 -32.00   0.50    0.05    -- -100.00  61.00 -30.00   58
 11  ω   -114.00 -57.00   0.50    0.05    --  -43.05 -45.00  75.00  114
 12  ω   -171.00 -92.00   0.50    0.05    -- -100.00-112.00-148.00  158
 13  ω   -174.00 -99.00   0.50    0.05    -- -100.00 -45.00  75.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0346690000
_diffrn_orient_matrix_UB_12      0.0676205000
_diffrn_orient_matrix_UB_13      0.0575274000
_diffrn_orient_matrix_UB_21      0.1583702000
_diffrn_orient_matrix_UB_22      -0.0370628000
_diffrn_orient_matrix_UB_23      -0.0052171000
_diffrn_orient_matrix_UB_31      0.0317059000
_diffrn_orient_matrix_UB_32      0.1109544000
_diffrn_orient_matrix_UB_33      -0.0367899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.586
_reflns_Friedel_fraction_full    0.810
_reflns_Friedel_fraction_max     0.719
_reflns_number_gt                3775
_reflns_number_total             4194
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      0.892
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1204
_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. Others
 Fixed Sof: C7(0.6) H7A(0.6) H7B(0.6) H7C(0.6) C17(0.4) H17A(0.4) H17B(0.4)
 H17C(0.4)
3.a Ternary CH refined with riding coordinates:
 C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C7(H7A,H7B,H7C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.69918(8) -0.54231(6) -0.12092(3) 0.0583(2) Uani 1 1 d . . . . .
O1 O -0.7814(3) -0.7628(2) -0.05970(11) 0.0729(6) Uani 1 1 d . . . . .
O2 O -0.3092(3) -0.4325(3) -0.04237(13) 0.0859(7) Uani 1 1 d . . . . .
O3 O -0.3543(3) -0.5694(2) -0.11007(12) 0.0758(7) Uani 1 1 d . . . . .
O4 O -0.3432(3) -0.4779(3) 0.16516(18) 0.1048(10) Uani 1 1 d . . . . .
O5 O -0.5048(3) -0.3418(2) 0.14421(13) 0.0879(8) Uani 1 1 d . . . . .
O6 O -0.6323(3) -0.42990(17) -0.12221(11) 0.0706(6) Uani 1 1 d . . . . .
O7 O -0.8499(2) -0.5502(2) -0.11492(11) 0.0769(7) Uani 1 1 d . . . . .
N1 N -0.6245(2) -0.60940(19) -0.06108(10) 0.0511(5) Uani 1 1 d . . . . .
C1 C -0.5139(3) -0.5492(2) -0.02961(12) 0.0499(6) Uani 1 1 d . . . . .
C2 C -0.5190(3) -0.5430(2) 0.02934(12) 0.0513(6) Uani 1 1 d . . . . .
H2 H -0.448696 -0.501665 0.049838 0.062 Uiso 1 1 calc R . . . .
C3 C -0.6384(3) -0.6026(2) 0.06330(12) 0.0506(6) Uani 1 1 d . . . . .
C4 C -0.6566(3) -0.7212(2) 0.03061(13) 0.0557(7) Uani 1 1 d . . . . .
H4A H -0.567666 -0.765129 0.033055 0.067 Uiso 1 1 calc R . . . .
H4B H -0.730823 -0.766716 0.050087 0.067 Uiso 1 1 calc R . . . .
C5 C -0.6957(3) -0.7039(2) -0.03339(13) 0.0545(6) Uani 1 1 d . . . . .
C6 C -0.3849(3) -0.5158(3) -0.06457(18) 0.0722(10) Uani 1 1 d . . . . .
C8 C -0.7791(3) -0.5333(2) 0.06126(12) 0.0534(6) Uani 1 1 d . . . . .
C9 C -0.7854(4) -0.4184(3) 0.04179(16) 0.0690(8) Uani 1 1 d . . . . .
H9 H -0.702729 -0.382337 0.027626 0.083 Uiso 1 1 calc R . . . .
C10 C -0.9131(5) -0.3559(4) 0.0430(2) 0.0887(12) Uani 1 1 d . . . . .
H10 H -0.915363 -0.278332 0.030232 0.106 Uiso 1 1 calc R . . . .
C11 C -1.0350(5) -0.4083(5) 0.0630(2) 0.0986(14) Uani 1 1 d . . . . .
H11 H -1.120819 -0.366762 0.062953 0.118 Uiso 1 1 calc R . . . .
C12 C -1.0325(4) -0.5225(5) 0.0833(2) 0.0932(14) Uani 1 1 d . . . . .
H12 H -1.115873 -0.557550 0.097405 0.112 Uiso 1 1 calc R . . . .
C13 C -0.9056(4) -0.5839(3) 0.08241(17) 0.0732(9) Uani 1 1 d . . . . .
H13 H -0.904036 -0.660834 0.096181 0.088 Uiso 1 1 calc R . . . .
C14 C -0.5957(4) -0.6299(3) 0.12819(13) 0.0622(7) Uani 1 1 d . . . . .
H14A H -0.501235 -0.665459 0.127771 0.075 Uiso 1 1 calc R . . . .
H14B H -0.662026 -0.688012 0.143524 0.075 Uiso 1 1 calc R . . . .
C15 C -0.5924(4) -0.5259(3) 0.17217(14) 0.0683(8) Uani 1 1 d . . . . .
H15 H -0.680881 -0.480283 0.167838 0.082 Uiso 1 1 calc R . . . .
C16 C -0.4663(4) -0.4476(3) 0.16070(15) 0.0694(8) Uani 1 1 d . . . . .
C18 C -0.3890(6) -0.2608(4) 0.1305(3) 0.1145(17) Uani 1 1 d . . . . .
H18A H -0.344111 -0.283633 0.093890 0.172 Uiso 1 1 calc GR . . . .
H18B H -0.319460 -0.262403 0.161981 0.172 Uiso 1 1 calc GR . . . .
H18C H -0.426864 -0.182886 0.126630 0.172 Uiso 1 1 calc GR . . . .
C19 C -0.5831(6) -0.5730(5) 0.23580(16) 0.1023(15) Uani 1 1 d . . . . .
H19A H -0.665670 -0.620541 0.244067 0.153 Uiso 1 1 calc GR . . . .
H19B H -0.579873 -0.508496 0.263202 0.153 Uiso 1 1 calc GR . . . .
H19C H -0.497845 -0.619460 0.240034 0.153 Uiso 1 1 calc GR . . . .
C20 C -0.6457(4) -0.6224(3) -0.18403(13) 0.0622(7) Uani 1 1 d . . . . .
C21 C -0.5451(5) -0.5743(4) -0.22161(16) 0.0796(10) Uani 1 1 d . . . . .
H21 H -0.502376 -0.502751 -0.212634 0.096 Uiso 1 1 calc R . . . .
C22 C -0.5086(6) -0.6343(5) -0.27313(18) 0.0999(14) Uani 1 1 d . . . . .
H22 H -0.441620 -0.602410 -0.299138 0.120 Uiso 1 1 calc R . . . .
C23 C -0.5705(6) -0.7398(5) -0.28583(19) 0.1011(15) Uani 1 1 d . . . . .
H23 H -0.545688 -0.779284 -0.320506 0.121 Uiso 1 1 calc R . . . .
C24 C -0.7066(5) -0.7300(4) -0.19607(17) 0.0870(11) Uani 1 1 d . . . . .
H24 H -0.772080 -0.763213 -0.169830 0.104 Uiso 1 1 calc R . . . .
C25 C -0.6687(7) -0.7877(4) -0.2478(2) 0.1095(17) Uani 1 1 d . . . . .
H25 H -0.710424 -0.859590 -0.256827 0.131 Uiso 1 1 calc R . . . .
C7 C -0.1804(7) -0.4122(8) -0.0783(4) 0.095(2) Uani 0.6 1 d . . P A 1
H7A H -0.207723 -0.395670 -0.118549 0.142 Uiso 0.6 1 calc GR . P A 1
H7B H -0.120847 -0.480868 -0.077384 0.142 Uiso 0.6 1 calc GR . P A 1
H7C H -0.128191 -0.346740 -0.062384 0.142 Uiso 0.6 1 calc GR . P A 1
C17 C -0.2152(9) -0.5208(10) -0.1337(5) 0.090(3) Uani 0.4 1 d . . P B 2
H17A H -0.186851 -0.564141 -0.168295 0.135 Uiso 0.4 1 calc GR . P B 2
H17B H -0.142276 -0.527501 -0.103717 0.135 Uiso 0.4 1 calc GR . P B 2
H17C H -0.227810 -0.439733 -0.143969 0.135 Uiso 0.4 1 calc GR . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O6 1.426(2) . ?
S1 O7 1.415(2) . ?
S1 N1 1.698(2) . ?
S1 C20 1.760(3) . ?
O1 C5 1.200(4) . ?
O2 C6 1.284(5) . ?
O2 C7 1.466(6) . ?
O3 C6 1.226(5) . ?
O3 C17 1.507(8) . ?
O4 C16 1.203(4) . ?
O5 C16 1.313(5) . ?
O5 C18 1.454(6) . ?
N1 C1 1.427(4) . ?
N1 C5 1.411(4) . ?
C1 C2 1.329(4) . ?
C1 C6 1.487(4) . ?
C2 C3 1.512(4) . ?
C3 C4 1.548(4) . ?
C3 C8 1.533(4) . ?
C3 C14 1.544(4) . ?
C4 C5 1.498(4) . ?
C8 C9 1.383(4) . ?
C8 C13 1.397(4) . ?
C9 C10 1.388(5) . ?
C10 C11 1.360(7) . ?
C11 C12 1.380(7) . ?
C12 C13 1.375(6) . ?
C14 C15 1.544(5) . ?
C15 C16 1.499(5) . ?
C15 C19 1.531(5) . ?
C20 C21 1.376(5) . ?
C20 C24 1.379(5) . ?
C21 C22 1.388(6) . ?
C22 C23 1.364(7) . ?
C23 C25 1.367(7) . ?
C24 C25 1.383(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
O6 S1 N1 103.99(13) . . ?
O6 S1 C20 109.02(15) . . ?
O7 S1 O6 119.60(16) . . ?
O7 S1 N1 107.63(14) . . ?
O7 S1 C20 109.00(16) . . ?
N1 S1 C20 106.83(13) . . ?
C6 O2 C7 110.7(4) . . ?
C6 O3 C17 108.1(6) . . ?
C16 O5 C18 116.1(3) . . ?
C1 N1 S1 118.24(18) . . ?
C5 N1 S1 120.1(2) . . ?
C5 N1 C1 119.2(2) . . ?
N1 C1 C6 116.5(3) . . ?
C2 C1 N1 119.7(2) . . ?
C2 C1 C6 122.9(3) . . ?
C1 C2 C3 120.4(3) . . ?
C2 C3 C4 103.5(2) . . ?
C2 C3 C8 112.5(2) . . ?
C2 C3 C14 112.2(2) . . ?
C8 C3 C4 110.1(2) . . ?
C8 C3 C14 110.7(2) . . ?
C14 C3 C4 107.5(2) . . ?
C5 C4 C3 111.6(2) . . ?
O1 C5 N1 121.5(3) . . ?
O1 C5 C4 124.3(3) . . ?
N1 C5 C4 114.2(2) . . ?
O2 C6 C1 115.4(3) . . ?
O3 C6 O2 124.4(3) . . ?
O3 C6 C1 120.1(3) . . ?
C9 C8 C3 122.3(3) . . ?
C9 C8 C13 117.6(3) . . ?
C13 C8 C3 120.0(3) . . ?
C8 C9 C10 121.1(4) . . ?
C11 C10 C9 119.9(4) . . ?
C10 C11 C12 120.7(4) . . ?
C13 C12 C11 119.4(4) . . ?
C12 C13 C8 121.4(4) . . ?
C3 C14 C15 117.1(3) . . ?
C16 C15 C14 111.2(3) . . ?
C16 C15 C19 109.0(3) . . ?
C19 C15 C14 109.3(3) . . ?
O4 C16 O5 123.3(4) . . ?
O4 C16 C15 124.3(4) . . ?
O5 C16 C15 112.4(3) . . ?
C21 C20 S1 118.8(3) . . ?
C21 C20 C24 121.0(3) . . ?
C24 C20 S1 120.2(3) . . ?
C20 C21 C22 118.9(4) . . ?
C23 C22 C21 120.4(4) . . ?
C22 C23 C25 120.3(4) . . ?
C20 C24 C25 118.9(4) . . ?
C23 C25 C24 120.5(4) . . ?

_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 2.699
_oxdiff_exptl_absorpt_empirical_full_min 0.444
