# 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. 
# 
#######################################################################

data_17augc_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2168612'
loop_
_audit_author_name
_audit_author_address
'Malleswara Rao Kuram'
;CSIR CDRI
India
;
_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_audit_creation_date             2022-04-25
_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         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_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                   9.6139(10)
_cell_length_b                   14.7059(13)
_cell_length_c                   10.8929(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.759(3)
_cell_angle_gamma                90
_cell_volume                     1513.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6485
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1213 before and 0.0728 after correction. The Ratio of minimum to maximum transmission is 0.8697. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25117
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         2.156
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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                3241
_reflns_number_total             3789
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      0.994
_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)+(0.0370P)²+0.9686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0927
_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 Ternary CH refined with riding coordinates:
 C00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I), C00K(H00K)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00J), C00M(H00L,H00M,H00N)
;
_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
S001 S 0.29300(3) 0.46041(2) 0.21399(3) 0.01490(9) Uani 1 1 d . . . . .
O002 O 0.30955(10) 0.47102(7) 0.52646(9) 0.0191(2) Uani 1 1 d . . . . .
O003 O 0.39744(11) 0.40455(7) 0.28916(9) 0.0211(2) Uani 1 1 d . . . . .
O004 O 0.17899(11) 0.41941(7) 0.12787(9) 0.0208(2) Uani 1 1 d . . . . .
N005 N 0.21965(12) 0.51936(8) 0.31456(11) 0.0160(2) Uani 1 1 d . . . . .
C006 C 0.37577(14) 0.54017(9) 0.13163(12) 0.0146(3) Uani 1 1 d . . . . .
C007 C 0.12239(14) 0.59117(9) 0.27380(13) 0.0161(3) Uani 1 1 d . . . . .
C008 C 0.23855(14) 0.63050(9) 0.47480(13) 0.0169(3) Uani 1 1 d . . . . .
C009 C 0.56028(15) 0.64898(9) 0.12947(13) 0.0192(3) Uani 1 1 d . . . . .
H009 H 0.642801 0.677424 0.169431 0.023 Uiso 1 1 calc R . . . .
C00A C 0.13146(13) 0.65771(9) 0.36663(12) 0.0153(3) Uani 1 1 d . . . . .
C00B C 0.49901(15) 0.67521(9) 0.00837(13) 0.0180(3) Uani 1 1 d . . . . .
C00C C 0.50040(14) 0.58130(9) 0.19131(13) 0.0181(3) Uani 1 1 d . . . . .
H00C H 0.542938 0.563646 0.271541 0.022 Uiso 1 1 calc R . . . .
C00D C -0.04912(15) 0.74325(10) 0.23396(14) 0.0214(3) Uani 1 1 d . . . . .
H00D H -0.106622 0.794447 0.219289 0.026 Uiso 1 1 calc R . . . .
C00E C 0.02718(14) 0.59861(10) 0.16149(13) 0.0183(3) Uani 1 1 d . . . . .
H00E H 0.020306 0.553590 0.100690 0.022 Uiso 1 1 calc R . . . .
C00F C -0.05790(14) 0.67627(10) 0.14327(13) 0.0205(3) Uani 1 1 d . . . . .
H00F H -0.121937 0.683191 0.068542 0.025 Uiso 1 1 calc R . . . .
C00G C 0.04545(14) 0.73424(9) 0.34699(13) 0.0192(3) Uani 1 1 d . . . . .
H00G H 0.050899 0.778771 0.408329 0.023 Uiso 1 1 calc R . . . .
C00H C 0.30624(14) 0.54251(9) 0.44047(12) 0.0160(3) Uani 1 1 d . . . . .
H00H H 0.403407 0.555658 0.430371 0.019 Uiso 1 1 calc R . . . .
C00I C 0.37627(15) 0.63118(10) -0.05051(13) 0.0211(3) Uani 1 1 d . . . . .
H00I H 0.335689 0.647130 -0.131951 0.025 Uiso 1 1 calc R . . . .
C1 C 0.27540(15) 0.67053(10) 0.58508(13) 0.0222(3) Uani 1 1 d . . . . .
H1A H 0.230673 0.723900 0.602067 0.027 Uiso 1 1 calc R . . . .
H1B H 0.345973 0.645243 0.645488 0.027 Uiso 1 1 calc R . . . .
C00K C 0.31338(15) 0.56396(10) 0.01004(13) 0.0193(3) Uani 1 1 d . . . . .
H00K H 0.231021 0.535315 -0.029883 0.023 Uiso 1 1 calc R . . . .
C00L C 0.56403(16) 0.74990(10) -0.05648(14) 0.0239(3) Uani 1 1 d . . . . .
H00A H 0.649403 0.728107 -0.080110 0.036 Uiso 1 1 calc GR . . . .
H00B H 0.585688 0.800756 -0.000939 0.036 Uiso 1 1 calc GR . . . .
H00J H 0.498503 0.768526 -0.129778 0.036 Uiso 1 1 calc GR . . . .
C00M C 0.17522(15) 0.44436(11) 0.55202(14) 0.0246(3) Uani 1 1 d . . . . .
H00L H 0.115591 0.424316 0.476156 0.037 Uiso 1 1 calc GR . . . .
H00M H 0.131825 0.495188 0.585410 0.037 Uiso 1 1 calc GR . . . .
H00N H 0.187796 0.395631 0.611716 0.037 Uiso 1 1 calc GR . . . .


_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
S001 O003 1.4305(10) . ?
S001 O004 1.4357(10) . ?
S001 N005 1.6545(12) . ?
S001 C006 1.7552(13) . ?
O002 C00H 1.4045(16) . ?
O002 C00M 1.4260(17) . ?
N005 C007 1.4254(17) . ?
N005 C00H 1.5045(17) . ?
C006 C00C 1.3904(18) . ?
C006 C00K 1.3927(18) . ?
C007 C00A 1.3980(18) . ?
C007 C00E 1.3887(19) . ?
C008 C00A 1.4682(18) . ?
C008 C00H 1.5260(19) . ?
C008 C1 1.3252(19) . ?
C009 C00B 1.3950(19) . ?
C009 C00C 1.3859(19) . ?
C00A C00G 1.3893(19) . ?
C00B C00I 1.393(2) . ?
C00B C00L 1.5036(19) . ?
C00D C00F 1.386(2) . ?
C00D C00G 1.394(2) . ?
C00E C00F 1.3972(19) . ?
C00I C00K 1.388(2) . ?

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
O003 S001 O004 120.10(6) . . ?
O003 S001 N005 105.20(6) . . ?
O003 S001 C006 109.86(6) . . ?
O004 S001 N005 106.55(6) . . ?
O004 S001 C006 108.08(6) . . ?
N005 S001 C006 106.15(6) . . ?
C00H O002 C00M 115.31(10) . . ?
C007 N005 S001 121.19(9) . . ?
C007 N005 C00H 109.60(10) . . ?
C00H N005 S001 119.37(9) . . ?
C00C C006 S001 119.01(10) . . ?
C00C C006 C00K 121.06(12) . . ?
C00K C006 S001 119.88(10) . . ?
C00A C007 N005 110.16(12) . . ?
C00E C007 N005 128.24(12) . . ?
C00E C007 C00A 121.60(12) . . ?
C00A C008 C00H 107.56(11) . . ?
C1 C008 C00A 129.43(13) . . ?
C1 C008 C00H 123.01(13) . . ?
C00C C009 C00B 121.19(13) . . ?
C007 C00A C008 109.23(12) . . ?
C00G C00A C007 120.04(12) . . ?
C00G C00A C008 130.72(12) . . ?
C009 C00B C00L 120.47(13) . . ?
C00I C00B C009 118.60(13) . . ?
C00I C00B C00L 120.93(13) . . ?
C009 C00C C006 119.01(12) . . ?
C00F C00D C00G 120.32(13) . . ?
C007 C00E C00F 117.49(13) . . ?
C00D C00F C00E 121.56(13) . . ?
C00A C00G C00D 118.98(13) . . ?
O002 C00H N005 112.24(10) . . ?
O002 C00H C008 115.39(11) . . ?
N005 C00H C008 103.09(10) . . ?
C00K C00I C00B 121.26(13) . . ?
C00I C00K C006 118.83(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
