# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ORTHO
_database_code_depnum_ccdc_archive 'CCDC 1978583'
loop_
_audit_author_name
_audit_author_address
'Prodeep Phukan'
;Gauahti University
India
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N-(tert-butyl)-N'-((4-nitrophenyl)sulfonyl)acetimidamide
_chemical_name_common            ?
_chemical_melting_point          403-404
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14.50 N3.50 O4 S'
_chemical_formula_weight         315.84

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      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   29.306(4)
_cell_length_b                   9.4752(9)
_cell_length_c                   11.4635(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3183.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.75

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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            29596
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.390
_diffrn_reflns_theta_max         29.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4248
_reflns_number_gt                3998
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.999

_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)+(0.2000P)²+0.4876P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0068(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   0.542
_refine_ls_restrained_S_all      0.542
_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
S1 S 0.68657(2) 0.90234(5) 0.49871(5) 0.03308(17) Uani 1 1 d . . . . .
N2 N 0.67304(6) 0.8104(2) 0.38694(15) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.48802(7) 0.8432(3) 0.7765(3) 0.0766(8) Uani 1 1 d . . . . .
O3 O 0.72554(6) 0.8481(3) 0.56151(16) 0.0531(5) Uani 1 1 d . . . . .
O4 O 0.68779(7) 1.0518(2) 0.47267(18) 0.0494(5) Uani 1 1 d . . . . .
C7 C 0.70231(6) 0.7918(2) 0.30143(18) 0.0350(4) Uani 1 1 d . . . . .
O1 O 0.53424(10) 0.8368(4) 0.9210(2) 0.0875(9) Uani 1 1 d . . . . .
C14 C 0.74984(8) 0.8523(3) 0.2982(3) 0.0570(8) Uani 1 1 d . . . . .
H14A H 0.7492 0.9482 0.3253 0.085 Uiso 1 1 calc R U . . .
H14B H 0.7612 0.8499 0.2197 0.085 Uiso 1 1 calc R U . . .
H14C H 0.7695 0.7975 0.3476 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0000 0.0000 0.4662(14) 0.188(7) Uani 1 2 d S T P . .
C9 C 0.60948(8) 0.7573(3) 0.1662(3) 0.0492(5) Uani 1 1 d . . . . .
H9A H 0.6074 0.8149 0.2349 0.074 Uiso 1 1 calc R U . . .
H9B H 0.5807 0.7116 0.1527 0.074 Uiso 1 1 calc R U . . .
H9C H 0.6170 0.8154 0.1003 0.074 Uiso 1 1 calc R U . . .
C8 C 0.64645(7) 0.6461(2) 0.18313(18) 0.0350(4) Uani 1 1 d . . . . .
N4 N 0.69076(6) 0.7150(2) 0.20946(17) 0.0382(4) Uani 1 1 d . . . . .
C4 C 0.63815(6) 0.8732(2) 0.58840(16) 0.0306(4) Uani 1 1 d . . . . .
C5 C 0.64536(7) 0.8705(2) 0.70817(18) 0.0347(4) Uani 1 1 d . . . . .
H5 H 0.6748 0.8765 0.7378 0.042 Uiso 1 1 calc R U . . .
C6 C 0.60855(7) 0.8587(2) 0.78351(19) 0.0386(4) Uani 1 1 d . . . . .
H6 H 0.6129 0.8557 0.8638 0.046 Uiso 1 1 calc R U . . .
C1 C 0.56536(7) 0.8517(2) 0.7361(2) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.52609(8) 0.8424(3) 0.8165(2) 0.0533(5) Uani 1 1 d . . . . .
C10 C 0.63334(11) 0.5437(3) 0.2796(3) 0.0530(6) Uani 1 1 d . . . . .
H10A H 0.6588 0.4833 0.2968 0.079 Uiso 1 1 calc R U . . .
H10B H 0.6079 0.4874 0.2545 0.079 Uiso 1 1 calc R U . . .
H10C H 0.6250 0.5956 0.3483 0.079 Uiso 1 1 calc R U . . .
C11 C 0.65376(12) 0.5671(4) 0.0694(3) 0.0657(8) Uani 1 1 d . . . . .
H11A H 0.6611 0.6330 0.0086 0.098 Uiso 1 1 calc R U . . .
H11B H 0.6264 0.5170 0.0491 0.098 Uiso 1 1 calc R U . . .
H11C H 0.6784 0.5012 0.0785 0.098 Uiso 1 1 calc R U . . .
C3 C 0.59428(8) 0.8663(3) 0.5422(2) 0.0417(5) Uani 1 1 d . . . . .
H3 H 0.5899 0.8684 0.4619 0.050 Uiso 1 1 calc R U . . .
C2 C 0.55695(8) 0.8561(3) 0.6170(2) 0.0464(5) Uani 1 1 d . . . . .
H2 H 0.5273 0.8524 0.5881 0.056 Uiso 1 1 calc R U . . .
C12 C 1.0000 0.0000 0.5889(10) 0.106(3) Uani 1 2 d S T P . .
N5 N 1.0000 0.0000 0.6832(12) 0.168(5) Uani 1 2 d S T P . .
H4A H 0.7123(11) 0.704(3) 0.161(3) 0.047(8) Uiso 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
S1 O3 1.4445(17) . ?
S1 O4 1.447(2) . ?
S1 N2 1.5995(17) . ?
S1 C4 1.774(2) . ?
N2 C7 1.314(3) . ?
O2 N1 1.206(3) . ?
C7 N4 1.325(3) . ?
C7 C14 1.507(3) . ?
O1 N1 1.223(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 C12 1.41(2) . ?
C9 C8 1.523(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 N4 1.484(3) . ?
C8 C11 1.519(3) . ?
C8 C10 1.521(3) . ?
N4 H4A 0.85(3) . ?
C4 C5 1.389(3) . ?
C4 C3 1.392(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.379(3) . ?
C6 H6 0.9300 . ?
C1 C2 1.388(3) . ?
C1 N1 1.477(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 C2 1.393(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C12 N5 1.081(15) . ?

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
O3 S1 O4 115.56(13) . . ?
O3 S1 N2 113.66(12) . . ?
O4 S1 N2 111.96(11) . . ?
O3 S1 C4 106.75(10) . . ?
O4 S1 C4 106.94(10) . . ?
N2 S1 C4 100.43(9) . . ?
C7 N2 S1 120.56(15) . . ?
N2 C7 N4 120.01(18) . . ?
N2 C7 C14 124.80(19) . . ?
N4 C7 C14 115.20(19) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C8 C11 105.54(19) . . ?
N4 C8 C10 110.73(19) . . ?
C11 C8 C10 110.2(2) . . ?
N4 C8 C9 110.12(17) . . ?
C11 C8 C9 109.4(2) . . ?
C10 C8 C9 110.8(2) . . ?
C7 N4 C8 128.82(18) . . ?
C7 N4 H4A 113(2) . . ?
C8 N4 H4A 118(2) . . ?
C5 C4 C3 121.05(19) . . ?
C5 C4 S1 116.99(15) . . ?
C3 C4 S1 121.71(16) . . ?
C6 C5 C4 119.91(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.22(19) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C1 C2 123.3(2) . . ?
C6 C1 N1 118.2(2) . . ?
C2 C1 N1 118.5(2) . . ?
O2 N1 O1 123.6(3) . . ?
O2 N1 C1 118.9(3) . . ?
O1 N1 C1 117.5(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
N5 C12 C13 180.0 . . ?

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
O3 S1 N2 C7 -59.9(2) . . . . ?
O4 S1 N2 C7 73.3(2) . . . . ?
C4 S1 N2 C7 -173.49(18) . . . . ?
S1 N2 C7 N4 179.78(17) . . . . ?
S1 N2 C7 C14 -0.2(3) . . . . ?
N2 C7 N4 C8 2.8(4) . . . . ?
C14 C7 N4 C8 -177.3(2) . . . . ?
C11 C8 N4 C7 -177.3(3) . . . . ?
C10 C8 N4 C7 -58.1(3) . . . . ?
C9 C8 N4 C7 64.7(3) . . . . ?
O3 S1 C4 C5 28.4(2) . . . . ?
O4 S1 C4 C5 -95.81(18) . . . . ?
N2 S1 C4 C5 147.22(17) . . . . ?
O3 S1 C4 C3 -157.3(2) . . . . ?
O4 S1 C4 C3 78.5(2) . . . . ?
N2 S1 C4 C3 -38.5(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
S1 C4 C5 C6 175.19(16) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C5 C6 C1 C2 -0.2(4) . . . . ?
C5 C6 C1 N1 -178.7(2) . . . . ?
C6 C1 N1 O2 176.3(3) . . . . ?
C2 C1 N1 O2 -2.2(4) . . . . ?
C6 C1 N1 O1 -2.4(4) . . . . ?
C2 C1 N1 O1 179.1(3) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
S1 C4 C3 C2 -174.2(2) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
N1 C1 C2 C3 179.4(2) . . . . ?
C4 C3 C2 C1 -0.7(4) . . . . ?

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.135


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
