# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_2ver0-20897_no2
_database_code_depnum_ccdc_archive 'CCDC 2143804'
loop_
_audit_author_name
_audit_author_address
'Alexey Dubovtsev'
;SPbSU
Russia
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-03-31 downloaded from the CCDC.
;
_audit_creation_date             2022-01-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
2-(Benzylsulfonyl)-1-(4-nitrophenyl)ethan-1-one
_chemical_formula_moiety         'C15 H13 N O5 S'
_chemical_formula_sum            'C15 H13 N O5 S'
_chemical_formula_weight         319.32
_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      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                   6.55290(10)
_cell_length_b                   7.72860(10)
_cell_length_c                   27.9324(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4490(10)
_cell_angle_gamma                90
_cell_volume                     1412.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1650
_cell_measurement_theta_min      3.1750
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.635
_exptl_absorpt_coefficient_mu    2.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            22270
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.832
_diffrn_reflns_theta_min         3.170
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2881
_reflns_number_total             3009
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.088
_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)+(0.0490P)²+0.4722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0878
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C14(H14), C15(H15), C6(H6), C11(H11), C12(H12), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.44745(4) 0.32038(3) 0.21861(2) 0.01536(11) Uani 1 1 d . . . . .
O1 O 0.58749(14) 0.43541(12) 0.19661(3) 0.0243(2) Uani 1 1 d . . . . .
O2 O 0.27622(14) 0.39861(12) 0.24066(3) 0.0231(2) Uani 1 1 d . . . . .
O3 O 0.79131(15) 0.39022(13) 0.30883(3) 0.0270(2) Uani 1 1 d . . . . .
O4 O 0.19567(18) 0.38623(17) 0.50366(4) 0.0401(3) Uani 1 1 d . . . . .
O5 O -0.02291(19) 0.21962(19) 0.46480(5) 0.0486(3) Uani 1 1 d . . . . .
N1 N 0.1370(2) 0.30306(17) 0.46807(4) 0.0319(3) Uani 1 1 d . . . . .
C10 C 0.50363(19) 0.29776(15) 0.34898(4) 0.0181(2) Uani 1 1 d . . . . .
C5 C 0.29307(19) 0.26639(16) 0.09132(4) 0.0211(2) Uani 1 1 d . . . . .
H5 H 0.4286 0.2325 0.0854 0.025 Uiso 1 1 calc R U . . .
C3 C 0.02147(19) 0.29604(16) 0.14523(4) 0.0198(2) Uani 1 1 d . . . . .
H3 H -0.0291 0.2805 0.1761 0.024 Uiso 1 1 calc R U . . .
C4 C 0.22014(18) 0.24470(14) 0.13676(4) 0.0172(2) Uani 1 1 d . . . . .
C7 C 0.35428(19) 0.16249(15) 0.17613(4) 0.0185(2) Uani 1 1 d . . . . .
H7A H 0.4712 0.1044 0.1620 0.022 Uiso 1 1 calc R U . . .
H7B H 0.2752 0.0737 0.1926 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4596(2) 0.37261(17) 0.43174(5) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.5097 0.4210 0.4614 0.029 Uiso 1 1 calc R U . . .
C8 C 0.58402(19) 0.19238(14) 0.26335(4) 0.0180(2) Uani 1 1 d . . . . .
H8A H 0.4988 0.0929 0.2721 0.022 Uiso 1 1 calc R U . . .
H8B H 0.7107 0.1468 0.2504 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5783(2) 0.37094(16) 0.39238(4) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.7115 0.4199 0.3949 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1667(2) 0.33789(17) 0.05452(5) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.2153 0.3507 0.0234 0.031 Uiso 1 1 calc R U . . .
C11 C 0.30747(19) 0.22584(16) 0.34509(4) 0.0200(2) Uani 1 1 d . . . . .
H11 H 0.2572 0.1755 0.3157 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1862(2) 0.22785(17) 0.38416(5) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.0524 0.1800 0.3819 0.028 Uiso 1 1 calc R U . . .
C9 C 0.63790(18) 0.30197(15) 0.30776(4) 0.0184(2) Uani 1 1 d . . . . .
C13 C 0.2652(2) 0.30150(17) 0.42653(5) 0.0238(3) Uani 1 1 d . . . . .
C1 C -0.0297(2) 0.39029(17) 0.06339(5) 0.0267(3) Uani 1 1 d . . . . .
H1 H -0.1149 0.4404 0.0384 0.032 Uiso 1 1 calc R U . . .
C2 C -0.10253(19) 0.36977(17) 0.10870(5) 0.0242(3) Uani 1 1 d . . . . .
H2 H -0.2371 0.4062 0.1147 0.029 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
S1 O1 1.4415(9) . ?
S1 O2 1.4446(9) . ?
S1 C7 1.7841(12) . ?
S1 C8 1.7908(12) . ?
O3 C9 1.2137(15) . ?
O4 N1 1.2260(18) . ?
O5 N1 1.2292(19) . ?
N1 C13 1.4730(17) . ?
C10 C15 1.3991(17) . ?
C10 C11 1.3987(17) . ?
C10 C9 1.4910(17) . ?
C5 H5 0.9500 . ?
C5 C4 1.3929(17) . ?
C5 C6 1.3947(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.3948(17) . ?
C3 C2 1.3880(18) . ?
C4 C7 1.5064(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.3847(19) . ?
C14 C13 1.387(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5256(16) . ?
C15 H15 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.386(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3881(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3853(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C2 H2 0.9500 . ?

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
O1 S1 O2 117.02(6) . . ?
O1 S1 C7 109.84(6) . . ?
O1 S1 C8 109.51(6) . . ?
O2 S1 C7 109.05(6) . . ?
O2 S1 C8 107.58(5) . . ?
C7 S1 C8 102.89(5) . . ?
O4 N1 O5 124.03(13) . . ?
O4 N1 C13 118.51(13) . . ?
O5 N1 C13 117.47(13) . . ?
C15 C10 C9 117.94(11) . . ?
C11 C10 C15 119.98(12) . . ?
C11 C10 C9 122.07(11) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.89(12) . . ?
C6 C5 H5 120.1 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.21(12) . . ?
C5 C4 C3 119.68(11) . . ?
C5 C4 C7 119.92(11) . . ?
C3 C4 C7 120.39(11) . . ?
S1 C7 H7A 109.4 . . ?
S1 C7 H7B 109.4 . . ?
C4 C7 S1 111.00(8) . . ?
C4 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C15 C14 H14 121.0 . . ?
C15 C14 C13 117.98(12) . . ?
C13 C14 H14 121.0 . . ?
S1 C8 H8A 109.7 . . ?
S1 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 S1 110.01(8) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.53(12) . . ?
C14 C15 H15 119.7 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.04(12) . . ?
C1 C6 H6 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.10(12) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.28(12) . . ?
C13 C12 H12 120.9 . . ?
O3 C9 C10 121.31(11) . . ?
O3 C9 C8 118.88(11) . . ?
C10 C9 C8 119.82(10) . . ?
C14 C13 N1 118.53(12) . . ?
C12 C13 N1 118.34(12) . . ?
C12 C13 C14 123.12(12) . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.23(12) . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 119.94(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?

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
S1 C8 C9 O3 -84.42(12) . . . . ?
S1 C8 C9 C10 96.17(11) . . . . ?
O1 S1 C7 C4 -67.62(10) . . . . ?
O1 S1 C8 C9 74.80(9) . . . . ?
O2 S1 C7 C4 61.85(10) . . . . ?
O2 S1 C8 C9 -53.36(10) . . . . ?
O4 N1 C13 C14 9.21(18) . . . . ?
O4 N1 C13 C12 -171.23(12) . . . . ?
O5 N1 C13 C14 -170.55(13) . . . . ?
O5 N1 C13 C12 9.01(19) . . . . ?
C10 C11 C12 C13 -0.34(18) . . . . ?
C5 C4 C7 S1 105.97(11) . . . . ?
C5 C6 C1 C2 -0.9(2) . . . . ?
C3 C4 C7 S1 -75.39(13) . . . . ?
C4 C5 C6 C1 1.22(19) . . . . ?
C4 C3 C2 C1 0.92(19) . . . . ?
C7 S1 C8 C9 -168.43(9) . . . . ?
C8 S1 C7 C4 175.85(9) . . . . ?
C15 C10 C11 C12 0.38(18) . . . . ?
C15 C10 C9 O3 -12.14(17) . . . . ?
C15 C10 C9 C8 167.26(11) . . . . ?
C15 C14 C13 N1 -179.76(11) . . . . ?
C15 C14 C13 C12 0.70(19) . . . . ?
C6 C5 C4 C3 -0.51(18) . . . . ?
C6 C5 C4 C7 178.13(11) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C11 C10 C15 C14 0.13(18) . . . . ?
C11 C10 C9 O3 166.96(12) . . . . ?
C11 C10 C9 C8 -13.64(17) . . . . ?
C11 C12 C13 N1 -179.74(11) . . . . ?
C11 C12 C13 C14 -0.20(19) . . . . ?
C9 C10 C15 C14 179.26(11) . . . . ?
C9 C10 C11 C12 -178.70(11) . . . . ?
C13 C14 C15 C10 -0.65(18) . . . . ?
C2 C3 C4 C5 -0.56(18) . . . . ?
C2 C3 C4 C7 -179.19(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
