# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20170116_CZ_xhd_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc23hdtv
_database_code_depnum_ccdc_archive 'CCDC 1951227'
loop_
_audit_author_name
_audit_author_address
'Hua-Dong Xu'
;Changzhou University
China
;
_audit_update_record             
;
2019-10-13 deposited with the CCDC.	2019-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O4 S'
_chemical_formula_weight         410.47

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.3192(14)
_cell_length_b                   11.674(2)
_cell_length_c                   23.041(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.345(6)
_cell_angle_gamma                90
_cell_volume                     1960.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6121
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.57
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10682
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3456
_reflns_number_gt                2982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.9732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5257(3) 0.48435(15) 0.33162(8) 0.0281(4) Uani 1 1 d . . . . .
H1 H 0.6157 0.4895 0.3058 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5711(3) 0.44442(16) 0.38786(8) 0.0348(5) Uani 1 1 d . . . . .
H2 H 0.6915 0.4235 0.3996 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4393(3) 0.43556(16) 0.42636(8) 0.0355(5) Uani 1 1 d . . . . .
H3 H 0.4710 0.4098 0.4642 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2588(3) 0.46507(17) 0.40880(8) 0.0350(5) Uani 1 1 d . . . . .
H4 H 0.1692 0.4582 0.4347 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2125(3) 0.50471(15) 0.35273(7) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.0912 0.5235 0.3410 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3457(2) 0.51682(14) 0.31367(7) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.2881(2) 0.55746(14) 0.25420(7) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.1752 0.5303 0.2380 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3743(2) 0.62711(14) 0.22057(7) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.3042(2) 0.66022(15) 0.15850(7) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.2675 0.7409 0.1591 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1353(2) 0.59076(17) 0.13528(7) 0.0271(4) Uani 1 1 d . . . . .
H10A H 0.1563 0.5104 0.1442 0.033 Uiso 1 1 calc R U . . .
H10B H 0.0300 0.6156 0.1546 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0941(3) 0.60512(17) 0.06976(8) 0.0326(5) Uani 1 1 d . . . . .
H11A H -0.0184 0.5651 0.0567 0.039 Uiso 1 1 calc R U . . .
H11B H 0.0778 0.6856 0.0603 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2521(3) 0.55684(17) 0.03917(8) 0.0335(5) Uani 1 1 d . . . . .
H12A H 0.2505 0.4739 0.0414 0.040 Uiso 1 1 calc R U . . .
H12B H 0.2375 0.5785 -0.0016 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4333(3) 0.60085(16) 0.06671(7) 0.0295(4) Uani 1 1 d . . . . .
H13 H 0.5353 0.5928 0.0458 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4575(2) 0.65026(15) 0.11857(7) 0.0236(4) Uani 1 1 d . . . . .
C15 C 0.6359(3) 0.70432(16) 0.14142(8) 0.0277(4) Uani 1 1 d . . . . .
H15A H 0.6221 0.7870 0.1415 0.033 Uiso 1 1 calc R U . . .
H15B H 0.7295 0.6853 0.1158 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6972(2) 0.66352(16) 0.20299(7) 0.0240(4) Uani 1 1 d . . . . .
H16A H 0.7303 0.5831 0.2021 0.029 Uiso 1 1 calc R U . . .
H16B H 0.8047 0.7064 0.2183 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7209(2) 0.77462(14) 0.33745(7) 0.0212(4) Uani 1 1 d . . . . .
C18 C 0.9014(2) 0.80552(15) 0.33152(8) 0.0249(4) Uani 1 1 d . . . . .
H18 H 0.9320 0.8408 0.2975 0.030 Uiso 1 1 calc R U . . .
C19 C 1.0360(3) 0.78341(16) 0.37663(8) 0.0272(4) Uani 1 1 d . . . . .
H19 H 1.1579 0.8029 0.3735 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9836(3) 0.73173(15) 0.42614(7) 0.0250(4) Uani 1 1 d . . . . .
C21 C 0.8043(3) 0.70321(16) 0.43334(8) 0.0287(4) Uani 1 1 d . . . . .
H21 H 0.7741 0.6695 0.4678 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6699(3) 0.72563(16) 0.38837(7) 0.0255(4) Uani 1 1 d . . . . .
H22 H 0.5477 0.7081 0.3923 0.031 Uiso 1 1 calc R U . . .
N1 N 0.54853(18) 0.67958(12) 0.24138(6) 0.0198(3) Uani 1 1 d . . . . .
N2 N 1.1281(2) 0.70291(14) 0.47299(7) 0.0309(4) Uani 1 1 d . . . . .
O1 O 0.37514(16) 0.80744(10) 0.30163(5) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.61555(17) 0.89198(10) 0.24619(5) 0.0263(3) Uani 1 1 d . . . . .
O3 O 1.2824(2) 0.74224(13) 0.47010(6) 0.0427(4) Uani 1 1 d . . . . .
O4 O 1.0863(2) 0.64047(14) 0.51209(6) 0.0431(4) Uani 1 1 d . . . . .
S1 S 0.54939(6) 0.79846(3) 0.27879(2) 0.01970(13) Uani 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
C1 C2 1.388(2) . ?
C1 C6 1.396(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(2) . ?
C7 C8 1.323(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.455(2) . ?
C8 C9 1.524(2) . ?
C9 C14 1.520(2) . ?
C9 C10 1.532(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.521(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.506(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.324(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.501(2) . ?
C15 C16 1.524(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N1 1.477(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.387(2) . ?
C17 C18 1.388(2) . ?
C17 S1 1.7791(17) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 N2 1.478(2) . ?
C21 C22 1.386(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 S1 1.6333(14) . ?
N2 O4 1.220(2) . ?
N2 O3 1.227(2) . ?
O1 S1 1.4282(13) . ?
O2 S1 1.4347(13) . ?

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 C6 120.31(18) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.46(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.95(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.87(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.76(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.59(16) . . ?
C5 C6 C7 118.43(16) . . ?
C1 C6 C7 122.89(16) . . ?
C8 C7 C6 129.15(16) . . ?
C8 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
C7 C8 N1 121.12(14) . . ?
C7 C8 C9 124.63(15) . . ?
N1 C8 C9 114.26(14) . . ?
C14 C9 C8 110.22(13) . . ?
C14 C9 C10 111.41(14) . . ?
C8 C9 C10 112.56(14) . . ?
C14 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C11 C10 C9 111.54(15) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 109.32(15) . . ?
C12 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C11 110.89(15) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 124.59(18) . . ?
C14 C13 H13 117.7 . . ?
C12 C13 H13 117.7 . . ?
C13 C14 C15 122.60(17) . . ?
C13 C14 C9 122.36(16) . . ?
C15 C14 C9 115.01(14) . . ?
C14 C15 C16 111.48(15) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N1 C16 C15 110.40(14) . . ?
N1 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C22 C17 C18 121.60(16) . . ?
C22 C17 S1 118.72(14) . . ?
C18 C17 S1 119.68(13) . . ?
C17 C18 C19 119.55(16) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 117.98(17) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C21 123.20(16) . . ?
C19 C20 N2 117.99(17) . . ?
C21 C20 N2 118.79(16) . . ?
C20 C21 C22 118.81(17) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C21 C22 C17 118.81(17) . . ?
C21 C22 H22 120.6 . . ?
C17 C22 H22 120.6 . . ?
C8 N1 C16 114.90(13) . . ?
C8 N1 S1 119.46(11) . . ?
C16 N1 S1 117.20(11) . . ?
O4 N2 O3 124.01(15) . . ?
O4 N2 C20 117.62(16) . . ?
O3 N2 C20 118.36(16) . . ?
O1 S1 O2 119.58(7) . . ?
O1 S1 N1 107.29(7) . . ?
O2 S1 N1 110.81(7) . . ?
O1 S1 C17 108.82(8) . . ?
O2 S1 C17 105.55(8) . . ?
N1 S1 C17 103.64(7) . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.046



