# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_DC5
_database_code_depnum_ccdc_archive 'CCDC 2208621'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University 
Canada
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        N-(4-cyanophenyl)-N-hydroxymethanesulfonamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N2 O3 S'
_chemical_formula_weight         212.22

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'
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'
N N 0.0311 0.0180 '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                   8.2861(15)
_cell_length_b                   5.4731(10)
_cell_length_c                   20.821(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.606(5)
_cell_angle_gamma                90
_cell_volume                     942.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1764
_cell_measurement_theta_min      5.882
_cell_measurement_theta_max      72.214

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.203
_exptl_absorpt_coefficient_mu    2.951
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13264
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         5.882
_diffrn_reflns_theta_max         72.214
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             1809
_reflns_number_gt                1764
_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 APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0495P)²+0.2907P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1809
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.002
_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 0.47316(17) 0.5915(3) 0.58373(7) 0.0361(3) Uani 1 1 d . . . . .
C2 C 0.32327(19) 0.6715(3) 0.55826(7) 0.0405(3) Uani 1 1 d . . . . .
H2 H 0.316274 0.810096 0.532401 0.049 Uiso 1 1 calc R U . . .
C3 C 0.18473(17) 0.5453(3) 0.57129(7) 0.0382(3) Uani 1 1 d . . . . .
H3 H 0.084119 0.597987 0.554398 0.046 Uiso 1 1 calc R U . . .
C4 C 0.19788(16) 0.3382(3) 0.61008(6) 0.0310(3) Uani 1 1 d . . . . .
C5 C 0.34738(19) 0.2544(3) 0.63436(8) 0.0359(3) Uani 1 1 d . . . . .
H5 H 0.354263 0.113118 0.659212 0.043 Uiso 1 1 calc R U . . .
N8 N 0.72613(18) 0.8449(3) 0.56171(8) 0.0551(4) Uani 1 1 d . . . . .
C7 C 0.6152(2) 0.7300(3) 0.57132(8) 0.0427(4) Uani 1 1 d . . . . .
C6 C 0.48609(17) 0.3807(3) 0.62162(7) 0.0393(3) Uani 1 1 d . . . . .
H6 H 0.586720 0.326186 0.638018 0.047 Uiso 1 1 calc R U . . .
O10 O -0.07552(14) 0.2632(2) 0.58127(6) 0.0470(3) Uani 1 1 d . . . . .
H10 H -0.123(2) 0.145(4) 0.5718(10) 0.071 Uiso 1 1 calc R U . . .
S11 S -0.00423(4) 0.26527(6) 0.70155(2) 0.03512(16) Uani 1 1 d . . . . .
C12 C -0.0369(2) 0.5814(3) 0.70397(8) 0.0454(4) Uani 1 1 d . . . . .
H12A H 0.065296 0.664621 0.707347 0.068 Uiso 1 1 calc R U . . .
H12B H -0.096854 0.620880 0.740559 0.068 Uiso 1 1 calc R U . . .
H12C H -0.096976 0.631979 0.665319 0.068 Uiso 1 1 calc R U . . .
O13 O -0.15511(14) 0.1401(2) 0.70359(7) 0.0536(3) Uani 1 1 d . . . . .
O14 O 0.12774(15) 0.2000(3) 0.74531(6) 0.0513(3) Uani 1 1 d . . . . .
N9 N 0.05703(14) 0.2039(2) 0.62633(6) 0.0343(3) 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 1.390(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.436(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 N9 1.4376(17) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
N8 C7 1.142(2) . ?
C6 H6 0.9300 . ?
O10 N9 1.4362(16) . ?
O10 H10 0.78(3) . ?
S11 O14 1.4241(12) . ?
S11 O13 1.4286(12) . ?
S11 N9 1.7098(13) . ?
S11 C12 1.7526(17) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C2 C1 C6 120.66(13) . . ?
C2 C1 C7 119.18(14) . . ?
C6 C1 C7 120.15(14) . . ?
C3 C2 C1 120.10(14) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.04(13) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.11(13) . . ?
C5 C4 N9 117.70(13) . . ?
C3 C4 N9 121.19(12) . . ?
C6 C5 C4 119.97(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N8 C7 C1 178.41(19) . . ?
C5 C6 C1 119.10(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N9 O10 H10 109.5 . . ?
O14 S11 O13 119.93(8) . . ?
O14 S11 N9 106.04(7) . . ?
O13 S11 N9 104.11(7) . . ?
O14 S11 C12 110.06(8) . . ?
O13 S11 C12 109.62(8) . . ?
N9 S11 C12 105.99(7) . . ?
S11 C12 H12A 109.5 . . ?
S11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O10 N9 C4 109.23(11) . . ?
O10 N9 S11 107.16(9) . . ?
C4 N9 S11 114.04(9) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050




