# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_210703d
_database_code_depnum_ccdc_archive 'CCDC 2122809'
loop_
_audit_author_name
_audit_author_address
'Yi-Long Zhu'
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-11-18 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(E)-N-methyl-N-(3-tosylprop-1-en-1-yl)benzamide
_chemical_formula_moiety         'C18 H19 N O3 S'
_chemical_formula_sum            'C18 H19 N O3 S'
_chemical_formula_weight         329.40
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4061(11)
_cell_length_b                   8.1735(8)
_cell_length_c                   18.7515(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.366(2)
_cell_angle_gamma                90
_cell_volume                     1707.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24,636
_cell_measurement_theta_min      2.224
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9378
_exptl_absorpt_correction_T_min  0.9141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8011
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.224
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2056
_reflns_number_total             3014
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.055
_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)+(0.0756P)²+0.9191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1681
_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:
 C10(H10A,H10B)
2.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N1 N 0.9124(3) 0.8179(3) 0.30854(15) 0.0552(8) Uani 1 1 d . . . . .
O1 O 1.1015(3) 0.7261(4) 0.34244(15) 0.0893(10) Uani 1 1 d . . . . .
O2 O 0.4608(2) 0.8866(3) 0.21928(12) 0.0562(7) Uani 1 1 d . . . . .
O3 O 0.4545(2) 1.0625(3) 0.11316(13) 0.0686(8) Uani 1 1 d . . . . .
S1 S 0.52027(7) 0.95452(11) 0.16645(4) 0.0447(3) Uani 1 1 d . . . . .
C1 C 1.0205(3) 0.7753(5) 0.2942(2) 0.0606(10) Uani 1 1 d . . . . .
C2 C 1.0372(3) 0.7863(5) 0.2181(2) 0.0540(9) Uani 1 1 d . . . . .
C3 C 0.9561(3) 0.7184(5) 0.1613(2) 0.0624(10) Uani 1 1 d . . . . .
H3 H 0.886619 0.669037 0.169304 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9786(4) 0.7239(6) 0.0929(2) 0.0803(13) Uani 1 1 d . . . . .
H4 H 0.923858 0.677495 0.054301 0.096 Uiso 1 1 calc R U . . .
C5 C 1.0794(4) 0.7959(7) 0.0798(3) 0.0855(14) Uani 1 1 d . . . . .
H5 H 1.092724 0.800491 0.032603 0.103 Uiso 1 1 calc R U . . .
C6 C 1.1600(4) 0.8608(6) 0.1361(3) 0.0782(13) Uani 1 1 d . . . . .
H6 H 1.229353 0.909437 0.127578 0.094 Uiso 1 1 calc R U . . .
C7 C 1.1407(3) 0.8556(5) 0.2054(3) 0.0668(11) Uani 1 1 d . . . . .
H7 H 1.197309 0.898881 0.243894 0.080 Uiso 1 1 calc R U . . .
C8 C 0.8298(3) 0.9109(4) 0.26060(17) 0.0446(8) Uani 1 1 d . . . . .
H8 H 0.851710 0.943183 0.217729 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7242(3) 0.9583(4) 0.26902(17) 0.0477(8) Uani 1 1 d . . . . .
H9 H 0.697322 0.927294 0.310478 0.057 Uiso 1 1 calc R U . . .
C10 C 0.6479(3) 1.0603(4) 0.21326(18) 0.0468(8) Uani 1 1 d . . . . .
H10A H 0.694167 1.096974 0.178516 0.056 Uiso 1 1 calc R U . . .
H10B H 0.622627 1.156318 0.236421 0.056 Uiso 1 1 calc R U . . .
C11 C 0.5750(3) 0.7938(4) 0.12169(16) 0.0409(7) Uani 1 1 d . . . . .
C12 C 0.5851(3) 0.6403(4) 0.15177(17) 0.0510(9) Uani 1 1 d . . . . .
H12 H 0.565542 0.622358 0.196810 0.061 Uiso 1 1 calc R U . . .
C13 C 0.6238(4) 0.5140(4) 0.11536(19) 0.0580(10) Uani 1 1 d . . . . .
H13 H 0.630229 0.409984 0.135925 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6537(3) 0.5372(5) 0.04880(18) 0.0534(9) Uani 1 1 d . . . . .
C15 C 0.6443(3) 0.6923(5) 0.02006(18) 0.0568(10) Uani 1 1 d . . . . .
H15 H 0.664945 0.710824 -0.024622 0.068 Uiso 1 1 calc R U . . .
C16 C 0.6052(3) 0.8200(4) 0.05584(17) 0.0507(9) Uani 1 1 d . . . . .
H16 H 0.599113 0.924223 0.035517 0.061 Uiso 1 1 calc R U . . .
C17 C 0.6955(4) 0.3983(5) 0.0092(2) 0.0794(13) Uani 1 1 d . . . . .
H17A H 0.696497 0.299823 0.037205 0.119 Uiso 1 1 calc R U . . .
H17B H 0.642064 0.384794 -0.037499 0.119 Uiso 1 1 calc R U . . .
H17C H 0.774986 0.420765 0.002314 0.119 Uiso 1 1 calc R U . . .
C18 C 0.8902(5) 0.7876(6) 0.3804(2) 0.0845(14) Uani 1 1 d . . . . .
H18A H 0.810757 0.823899 0.382137 0.127 Uiso 1 1 calc R U . . .
H18B H 0.897107 0.672579 0.390822 0.127 Uiso 1 1 calc R U . . .
H18C H 0.947848 0.846269 0.416103 0.127 Uiso 1 1 calc R U . . .


_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
N1 C1 1.362(5) . ?
N1 C8 1.383(4) . ?
N1 C18 1.446(5) . ?
O1 C1 1.214(4) . ?
O2 S1 1.427(2) . ?
O3 S1 1.421(2) . ?
S1 C10 1.757(3) . ?
S1 C11 1.745(3) . ?
C1 C2 1.484(5) . ?
C2 C3 1.370(5) . ?
C2 C7 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.360(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.306(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.469(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.370(4) . ?
C11 C16 1.368(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.362(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(5) . ?
C14 C15 1.372(5) . ?
C14 C17 1.490(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(5) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 122.2(3) . . ?
C1 N1 C18 119.1(3) . . ?
C8 N1 C18 118.0(3) . . ?
O2 S1 C10 108.07(15) . . ?
O2 S1 C11 108.26(15) . . ?
O3 S1 O2 118.17(16) . . ?
O3 S1 C10 107.55(16) . . ?
O3 S1 C11 108.59(15) . . ?
C11 S1 C10 105.50(15) . . ?
N1 C1 C2 118.8(3) . . ?
O1 C1 N1 121.0(4) . . ?
O1 C1 C2 120.2(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 C7 119.6(4) . . ?
C7 C2 C1 118.9(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
N1 C8 H8 116.5 . . ?
C9 C8 N1 127.0(3) . . ?
C9 C8 H8 116.5 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
S1 C10 H10A 109.2 . . ?
S1 C10 H10B 109.2 . . ?
C9 C10 S1 112.2(2) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 S1 119.9(2) . . ?
C16 C11 S1 120.1(3) . . ?
C16 C11 C12 120.0(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C17 121.0(4) . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 C17 121.0(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N1 C1 C2 C3 -49.9(5) . . . . ?
N1 C1 C2 C7 135.0(4) . . . . ?
N1 C8 C9 C10 178.7(3) . . . . ?
O1 C1 C2 C3 128.8(4) . . . . ?
O1 C1 C2 C7 -46.3(5) . . . . ?
O2 S1 C10 C9 52.6(3) . . . . ?
O2 S1 C11 C12 -16.9(3) . . . . ?
O2 S1 C11 C16 161.5(3) . . . . ?
O3 S1 C10 C9 -178.8(2) . . . . ?
O3 S1 C11 C12 -146.4(3) . . . . ?
O3 S1 C11 C16 32.1(3) . . . . ?
S1 C11 C12 C13 177.7(3) . . . . ?
S1 C11 C16 C15 -177.9(3) . . . . ?
C1 N1 C8 C9 -180.0(3) . . . . ?
C1 C2 C3 C4 -176.5(4) . . . . ?
C1 C2 C7 C6 177.3(4) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C2 C7 C6 2.0(6) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 C7 -0.5(7) . . . . ?
C5 C6 C7 C2 -1.1(6) . . . . ?
C7 C2 C3 C4 -1.4(6) . . . . ?
C8 N1 C1 O1 163.5(3) . . . . ?
C8 N1 C1 C2 -17.8(5) . . . . ?
C8 C9 C10 S1 111.2(3) . . . . ?
C10 S1 C11 C12 98.6(3) . . . . ?
C10 S1 C11 C16 -83.0(3) . . . . ?
C11 S1 C10 C9 -63.0(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C11 C16 C15 0.6(5) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C12 C13 C14 C17 -179.7(4) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C11 0.2(5) . . . . ?
C16 C11 C12 C13 -0.8(5) . . . . ?
C17 C14 C15 C16 179.5(4) . . . . ?
C18 N1 C1 O1 -6.6(6) . . . . ?
C18 N1 C1 C2 172.1(4) . . . . ?
C18 N1 C8 C9 -9.7(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
