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

data_mo_20200720a_0m_sq
_audit_block_doi                 10.5517/ccdc.csd.cc2750gx
_database_code_depnum_ccdc_archive 'CCDC 2060398'
loop_
_audit_author_name
_audit_author_address
'Sun Pengpeng'
;Anhui Normal University
China
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 N2 O3 S'
_chemical_formula_sum            'C24 H26 N2 O3 S'
_chemical_formula_weight         422.53
_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                   9.5460(6)
_cell_length_b                   9.1361(5)
_cell_length_c                   29.2032(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.827(2)
_cell_angle_gamma                90
_cell_volume                     2541.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1247 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.9217.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            54642
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         3.061
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                3909
_reflns_number_total             5899
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    ?
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.017
_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)+(0.0895P)²+1.1829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1766
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C17(H17), C18(H18), N1(H1)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.5196(3) 0.3220(4) 0.84189(10) 0.0717(8) Uani 1 1 d . . . . .
H1A H 0.506197 0.409939 0.859037 0.107 Uiso 1 1 calc GR . . . .
H1B H 0.618215 0.302558 0.841027 0.107 Uiso 1 1 calc GR . . . .
H1C H 0.475144 0.241552 0.856344 0.107 Uiso 1 1 calc GR . . . .
C2 C 0.4550(2) 0.3407(3) 0.79325(9) 0.0501(6) Uani 1 1 d . . . . .
C3 C 0.3718(2) 0.4600(3) 0.78075(8) 0.0499(6) Uani 1 1 d . . . . .
H3 H 0.356885 0.532175 0.802359 0.060 Uiso 1 1 calc R . . . .
C4 C 0.3106(2) 0.4739(3) 0.73682(8) 0.0471(5) Uani 1 1 d . . . . .
H4 H 0.255335 0.555053 0.728924 0.057 Uiso 1 1 calc R . . . .
C5 C 0.3319(2) 0.3668(2) 0.70460(8) 0.0411(5) Uani 1 1 d . . . . .
C6 C 0.4179(2) 0.2476(3) 0.71629(9) 0.0497(6) Uani 1 1 d . . . . .
H6 H 0.434565 0.176537 0.694520 0.060 Uiso 1 1 calc R . . . .
C7 C 0.4782(3) 0.2358(3) 0.76027(9) 0.0536(6) Uani 1 1 d . . . . .
H7 H 0.535422 0.155975 0.768021 0.064 Uiso 1 1 calc R . . . .
C8 C 0.5022(2) 0.4215(2) 0.61242(7) 0.0412(5) Uani 1 1 d . . . . .
C9 C 0.5234(3) 0.3058(3) 0.58283(8) 0.0566(6) Uani 1 1 d . . . . .
H9 H 0.446580 0.258646 0.568153 0.068 Uiso 1 1 calc R . . . .
C10 C 0.6578(3) 0.2604(3) 0.57505(9) 0.0630(7) Uani 1 1 d . . . . .
H10 H 0.671515 0.182267 0.555433 0.076 Uiso 1 1 calc R . . . .
C11 C 0.7712(3) 0.3315(3) 0.59649(9) 0.0602(7) Uani 1 1 d . . . . .
H11 H 0.861887 0.302673 0.590801 0.072 Uiso 1 1 calc R . . . .
C12 C 0.7507(2) 0.4457(3) 0.62652(8) 0.0490(6) Uani 1 1 d . . . . .
H12 H 0.828252 0.492463 0.640900 0.059 Uiso 1 1 calc R . . . .
C13 C 0.6159(2) 0.4922(2) 0.63563(7) 0.0381(5) Uani 1 1 d . . . . .
C14 C 0.5985(2) 0.6039(2) 0.67234(7) 0.0353(4) Uani 1 1 d . . . . .
C15 C 0.6617(2) 0.5738(2) 0.71595(7) 0.0405(5) Uani 1 1 d . . . . .
H15 H 0.717736 0.490802 0.719669 0.049 Uiso 1 1 calc R . . . .
C16 C 0.6448(2) 0.6614(3) 0.75373(7) 0.0434(5) Uani 1 1 d . . . . .
C17 C 0.5601(2) 0.7832(3) 0.74770(8) 0.0482(5) Uani 1 1 d . . . . .
H17 H 0.543122 0.841380 0.772848 0.058 Uiso 1 1 calc R . . . .
C18 C 0.5002(2) 0.8200(2) 0.70484(8) 0.0464(5) Uani 1 1 d . . . . .
H18 H 0.445389 0.903983 0.701542 0.056 Uiso 1 1 calc R . . . .
C19 C 0.5203(2) 0.7334(2) 0.66640(7) 0.0383(5) Uani 1 1 d . . . . .
C20 C 0.7134(3) 0.6229(3) 0.79992(8) 0.0583(7) Uani 1 1 d . . . . .
H20A H 0.751645 0.525899 0.798945 0.087 Uiso 1 1 calc GR . . . .
H20B H 0.644958 0.626944 0.822533 0.087 Uiso 1 1 calc GR . . . .
H20C H 0.787392 0.691379 0.807829 0.087 Uiso 1 1 calc GR . . . .
C21 C 0.5614(3) 0.8043(3) 0.58786(8) 0.0542(6) Uani 1 1 d . . . . .
H21A H 0.631451 0.727430 0.587739 0.065 Uiso 1 1 calc R . . . .
H21B H 0.608778 0.895341 0.596231 0.065 Uiso 1 1 calc R . . . .
C22 C 0.4884(3) 0.8184(4) 0.54090(9) 0.0723(8) Uani 1 1 d . . . . .
H22A H 0.556831 0.842503 0.518990 0.087 Uiso 1 1 calc R . . . .
H22B H 0.446142 0.725256 0.531968 0.087 Uiso 1 1 calc R . . . .
C23 C 0.2841(3) 0.8955(4) 0.57244(11) 0.0749(9) Uani 1 1 d . . . . .
H23A H 0.237948 0.803458 0.564500 0.090 Uiso 1 1 calc R . . . .
H23B H 0.212910 0.971397 0.571631 0.090 Uiso 1 1 calc R . . . .
C24 C 0.3525(3) 0.8851(3) 0.61990(9) 0.0580(6) Uani 1 1 d . . . . .
H24A H 0.396152 0.977896 0.628490 0.070 Uiso 1 1 calc R . . . .
H24B H 0.282442 0.863500 0.641498 0.070 Uiso 1 1 calc R . . . .
N1 N 0.36184(19) 0.4702(2) 0.61825(6) 0.0439(4) Uani 1 1 d . . . . .
H1 H 0.333640 0.550247 0.605176 0.053 Uiso 1 1 calc R . . . .
N2 N 0.45869(19) 0.76957(19) 0.62160(6) 0.0412(4) Uani 1 1 d . . . . .
O1 O 0.13215(17) 0.4716(2) 0.64965(7) 0.0646(5) Uani 1 1 d . . . . .
O2 O 0.2407(2) 0.23515(19) 0.63062(7) 0.0653(5) Uani 1 1 d . . . . .
O3 O 0.3829(2) 0.9279(2) 0.53953(7) 0.0781(6) Uani 1 1 d . . . . .
S1 S 0.25357(6) 0.38041(6) 0.64855(2) 0.04801(19) 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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.520(4) . ?
C2 C3 1.383(3) . ?
C2 C7 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C6 1.393(3) . ?
C5 S1 1.758(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(3) . ?
C8 C13 1.399(3) . ?
C8 N1 1.432(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(3) . ?
C13 C14 1.497(3) . ?
C14 C15 1.400(3) . ?
C14 C19 1.404(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 C17 1.380(3) . ?
C16 C20 1.501(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(3) . ?
C19 N2 1.437(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(4) . ?
C21 N2 1.470(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 O3 1.418(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.495(4) . ?
C23 O3 1.422(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 N2 1.462(3) . ?
N1 H1 0.8600 . ?
N1 S1 1.627(2) . ?
O1 S1 1.4297(18) . ?
O2 S1 1.4289(18) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 C7 118.5(2) . . ?
C7 C2 C1 119.9(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 S1 120.77(17) . . ?
C6 C5 S1 119.38(18) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C13 120.8(2) . . ?
C9 C8 N1 119.1(2) . . ?
C13 C8 N1 120.06(19) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C14 122.80(19) . . ?
C12 C13 C8 117.5(2) . . ?
C12 C13 C14 119.4(2) . . ?
C15 C14 C13 117.12(18) . . ?
C15 C14 C19 118.12(19) . . ?
C19 C14 C13 124.72(18) . . ?
C14 C15 H15 118.4 . . ?
C16 C15 C14 123.2(2) . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C20 121.0(2) . . ?
C17 C16 C15 117.6(2) . . ?
C17 C16 C20 121.3(2) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 N2 119.23(18) . . ?
C18 C19 C14 118.60(19) . . ?
C18 C19 N2 122.12(19) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
N2 C21 H21A 109.7 . . ?
N2 C21 H21B 109.7 . . ?
N2 C21 C22 109.9(2) . . ?
C21 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O3 C22 C21 111.8(2) . . ?
O3 C22 H22A 109.2 . . ?
O3 C22 H22B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
O3 C23 H23A 109.3 . . ?
O3 C23 H23B 109.3 . . ?
O3 C23 C24 111.8(2) . . ?
C23 C24 H24A 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N2 C24 C23 109.7(2) . . ?
N2 C24 H24A 109.7 . . ?
N2 C24 H24B 109.7 . . ?
C8 N1 H1 118.6 . . ?
C8 N1 S1 122.76(15) . . ?
S1 N1 H1 118.6 . . ?
C19 N2 C21 114.15(18) . . ?
C19 N2 C24 115.95(18) . . ?
C24 N2 C21 108.25(19) . . ?
C22 O3 C23 109.6(2) . . ?
N1 S1 C5 107.22(10) . . ?
O1 S1 C5 108.37(11) . . ?
O1 S1 N1 105.30(11) . . ?
O2 S1 C5 107.25(11) . . ?
O2 S1 N1 108.11(11) . . ?
O2 S1 O1 119.99(12) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.498 -0.048 0.000 263 61 ' '
2 0.002 -0.010 0.500 263 61 ' '

_platon_squeeze_void_probe_radius 1.20
_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_mo_20200731a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2750jz
_database_code_depnum_ccdc_archive 'CCDC 2060400'
loop_
_audit_author_name
_audit_author_address
'Sun Pengpeng'
;Anhui Normal University
China
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N2 O3 S'
_chemical_formula_weight         420.51

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                   8.8985(3)
_cell_length_b                   22.3112(9)
_cell_length_c                   10.5503(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.4750(10)
_cell_angle_gamma                90
_cell_volume                     2052.75(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.187
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.964
_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      273(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            50315
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4707
_reflns_number_gt                3744
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.0555P)²+0.9400P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0083(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4707
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.001

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 0.5923(3) 0.13513(9) 0.5949(3) 0.0653(6) Uani 1 1 d . . . . .
H1A H 0.501919 0.111304 0.567196 0.098 Uiso 1 1 calc R U . . .
H1B H 0.635684 0.126296 0.683709 0.098 Uiso 1 1 calc R U . . .
H1C H 0.665823 0.126083 0.542280 0.098 Uiso 1 1 calc R U . . .
C2 C 0.5507(2) 0.20069(8) 0.58165(18) 0.0435(4) Uani 1 1 d . . . . .
C3 C 0.6551(2) 0.24428(8) 0.63622(19) 0.0459(4) Uani 1 1 d . . . . .
H3 H 0.749629 0.232536 0.684467 0.055 Uiso 1 1 calc R U . . .
C4 C 0.62216(19) 0.30457(8) 0.62065(18) 0.0414(4) Uani 1 1 d . . . . .
H4 H 0.694129 0.333012 0.657508 0.050 Uiso 1 1 calc R U . . .
C5 C 0.48119(18) 0.32248(7) 0.54978(15) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.3729(2) 0.27999(8) 0.49731(18) 0.0403(4) Uani 1 1 d . . . . .
H6 H 0.277022 0.291789 0.451766 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4093(2) 0.21958(8) 0.5136(2) 0.0473(4) Uani 1 1 d . . . . .
H7 H 0.336872 0.191096 0.477818 0.057 Uiso 1 1 calc R U . . .
C8 C 0.46391(16) 0.42649(7) 0.77015(15) 0.0297(3) Uani 1 1 d . . . . .
C9 C 0.56741(19) 0.47333(8) 0.80340(19) 0.0408(4) Uani 1 1 d . . . . .
H9 H 0.572714 0.504064 0.744899 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6623(2) 0.47375(9) 0.9242(2) 0.0520(5) Uani 1 1 d . . . . .
H10 H 0.731393 0.504982 0.947748 0.062 Uiso 1 1 calc R U . . .
C11 C 0.6542(2) 0.42785(10) 1.0095(2) 0.0544(5) Uani 1 1 d . . . . .
H11 H 0.719452 0.427918 1.090185 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5505(2) 0.38171(9) 0.97714(18) 0.0458(4) Uani 1 1 d . . . . .
H12 H 0.546029 0.351283 1.036525 0.055 Uiso 1 1 calc R U . . .
C13 C 0.45213(18) 0.38012(7) 0.85617(15) 0.0327(3) Uani 1 1 d . . . . .
C14 C 0.33922(18) 0.33123(7) 0.81991(15) 0.0318(3) Uani 1 1 d . . . . .
C15 C 0.3804(2) 0.27191(7) 0.85010(16) 0.0391(4) Uani 1 1 d . . . . .
H15 H 0.480616 0.263481 0.891212 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2767(2) 0.22482(7) 0.82085(18) 0.0443(4) Uani 1 1 d . . . . .
C17 C 0.1289(2) 0.23857(8) 0.76076(19) 0.0469(5) Uani 1 1 d . . . . .
H17 H 0.057093 0.207933 0.741913 0.056 Uiso 1 1 calc R U . . .
C18 C 0.0844(2) 0.29714(8) 0.72753(18) 0.0402(4) Uani 1 1 d . . . . .
H18 H -0.015846 0.304964 0.685516 0.048 Uiso 1 1 calc R U . . .
C19 C 0.18808(18) 0.34413(7) 0.75644(15) 0.0310(3) Uani 1 1 d . . . . .
C20 C 0.3266(3) 0.16102(9) 0.8536(2) 0.0643(6) Uani 1 1 d . . . . .
H20A H 0.244906 0.139493 0.880471 0.096 Uiso 1 1 calc R U . . .
H20B H 0.415279 0.161005 0.922379 0.096 Uiso 1 1 calc R U . . .
H20C H 0.351351 0.142012 0.778711 0.096 Uiso 1 1 calc R U . . .
C21 C 0.20347(16) 0.43553(7) 0.62990(14) 0.0276(3) Uani 1 1 d . . . . .
H21 H 0.148348 0.421145 0.545638 0.033 Uiso 1 1 calc R U . . .
C22 C 0.18031(18) 0.50285(7) 0.64117(17) 0.0354(4) Uani 1 1 d . . . . .
H22A H 0.244734 0.517100 0.720603 0.042 Uiso 1 1 calc R U . . .
H22B H 0.213084 0.522773 0.569576 0.042 Uiso 1 1 calc R U . . .
C23 C -0.0323(2) 0.48739(8) 0.73731(18) 0.0417(4) Uani 1 1 d . . . . .
H23A H -0.139467 0.497624 0.731006 0.050 Uiso 1 1 calc R U . . .
H23B H 0.023004 0.499648 0.822035 0.050 Uiso 1 1 calc R U . . .
C24 C -0.01732(18) 0.42029(7) 0.72329(18) 0.0369(4) Uani 1 1 d . . . . .
H24A H -0.058009 0.399854 0.790309 0.044 Uiso 1 1 calc R U . . .
H24B H -0.075082 0.407402 0.639902 0.044 Uiso 1 1 calc R U . . .
N1 N 0.36804(14) 0.42458(6) 0.64312(12) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.14533(14) 0.40536(5) 0.73430(13) 0.0296(3) Uani 1 1 d . . . . .
O1 O 0.58836(15) 0.42802(6) 0.53301(15) 0.0520(4) Uani 1 1 d . . . . .
O2 O 0.32825(17) 0.40593(6) 0.40826(12) 0.0504(3) Uani 1 1 d . . . . .
O3 O 0.02613(13) 0.51881(5) 0.64096(13) 0.0427(3) Uani 1 1 d . . . . .
S1 S 0.44292(5) 0.39962(2) 0.52328(4) 0.03498(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 1.508(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.385(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 S1 1.7661(16) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.391(2) . ?
C8 C13 1.394(2) . ?
C8 N1 1.4390(19) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.481(2) . ?
C14 C15 1.393(2) . ?
C14 C19 1.408(2) . ?
C15 C16 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 C20 1.511(2) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9300 . ?
C19 N2 1.4249(19) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N1 1.4637(18) . ?
C21 N2 1.4699(19) . ?
C21 C22 1.524(2) . ?
C21 H21 0.9800 . ?
C22 O3 1.4170(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O3 1.416(2) . ?
C23 C24 1.513(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N2 1.4671(19) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N1 S1 1.6395(13) . ?
O1 S1 1.4262(13) . ?
O2 S1 1.4287(14) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.77(17) . . ?
C7 C2 C1 121.63(19) . . ?
C3 C2 C1 120.60(19) . . ?
C4 C3 C2 121.66(17) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.58(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.09(16) . . ?
C4 C5 S1 119.46(13) . . ?
C6 C5 S1 120.43(13) . . ?
C5 C6 C7 119.19(17) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 121.68(17) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C13 121.68(15) . . ?
C9 C8 N1 119.81(14) . . ?
C13 C8 N1 118.49(13) . . ?
C10 C9 C8 119.34(17) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 119.80(17) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.89(18) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.79(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 117.48(16) . . ?
C8 C13 C14 120.90(14) . . ?
C12 C13 C14 121.62(15) . . ?
C15 C14 C19 119.06(15) . . ?
C15 C14 C13 120.44(15) . . ?
C19 C14 C13 120.48(13) . . ?
C16 C15 C14 122.25(17) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C17 C16 C15 117.68(16) . . ?
C17 C16 C20 121.75(19) . . ?
C15 C16 C20 120.57(19) . . ?
C16 C17 C18 121.62(17) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 120.67(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 118.69(15) . . ?
C18 C19 N2 122.91(15) . . ?
C14 C19 N2 118.20(13) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 N2 110.29(12) . . ?
N1 C21 C22 107.78(12) . . ?
N2 C21 C22 108.64(12) . . ?
N1 C21 H21 110.0 . . ?
N2 C21 H21 110.0 . . ?
C22 C21 H21 110.0 . . ?
O3 C22 C21 113.17(13) . . ?
O3 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
O3 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
O3 C23 C24 111.57(14) . . ?
O3 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
O3 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N2 C24 C23 108.76(13) . . ?
N2 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
N2 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C8 N1 C21 118.71(12) . . ?
C8 N1 S1 118.14(10) . . ?
C21 N1 S1 122.39(10) . . ?
C19 N2 C24 117.24(12) . . ?
C19 N2 C21 116.08(12) . . ?
C24 N2 C21 108.99(12) . . ?
C23 O3 C22 111.60(12) . . ?
O1 S1 O2 120.13(9) . . ?
O1 S1 N1 107.21(8) . . ?
O2 S1 N1 106.88(7) . . ?
O1 S1 C5 106.14(8) . . ?
O2 S1 C5 108.25(8) . . ?
N1 S1 C5 107.70(7) . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.047



