# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_nm-1287-crysalis
_database_code_depnum_ccdc_archive 'CCDC 2261525'
loop_
_audit_author_name
_audit_author_address
'NILANJANA MUKHERJEE'
;BITS Pilani Hyderabad Campus
India
;
_audit_update_record             
;
2023-05-09 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        NM-1287
_chemical_formula_moiety         'C17 H18 S'
_chemical_formula_sum            'C17 H18 S'
_chemical_formula_weight         254.37
_chemical_absolute_configuration ?
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4617(5)
_cell_length_b                   11.8672(7)
_cell_length_c                   13.2190(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1484.28(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2648
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1160
_cell_measurement_theta_min      4.9460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             544
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5041
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.763
_diffrn_reflns_theta_min         5.008
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  25.00   0.50   10.00    --    0.00  37.00-180.00   88
  2  ω     53.00  79.00   0.50   10.00    --    0.00  37.00-180.00   52
  3  ω     39.00  82.00   0.50   10.00    --    0.00  77.00-180.00   86
  4  ω    140.00 166.00   0.50   40.00    --  107.20  45.00  90.00   52
  5  ω     29.00  58.00   0.50   40.00    --  107.20 -30.00  30.00   58
  6  ω     63.00 125.00   0.50   40.00    --  107.20 -30.00  30.00  124
  7  ω     18.00 132.00   0.50   40.00    --  107.20 -61.00 -60.00  228
  8  ω     88.00 115.00   0.50   40.00    --  107.20  61.00 -90.00   54
  9  ω    114.00 181.00   0.50   40.00    --  107.20  77.00 -60.00  134
 10  ω     88.00 127.00   0.50   40.00    --  107.20  45.00  90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1109406000
_diffrn_orient_matrix_UB_12      -0.0756063000
_diffrn_orient_matrix_UB_13      -0.0514351000
_diffrn_orient_matrix_UB_21      -0.0427378000
_diffrn_orient_matrix_UB_22      0.0477882000
_diffrn_orient_matrix_UB_23      -0.1039694000
_diffrn_orient_matrix_UB_31      0.1113287000
_diffrn_orient_matrix_UB_32      0.0939978000
_diffrn_orient_matrix_UB_33      0.0114561000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.710
_reflns_number_gt                2395
_reflns_number_total             2754
_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       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.084
_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)+(0.0614P)²+0.1737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009)
2.b Idealised Me refined as rotating group:
 C00G(H00b,H00d,H00g), C1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   mixed
_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
S001 S 0.68093(9) 0.72139(8) 0.45183(7) 0.0717(3) Uani 1 1 d . . . . .
C002 C 0.4845(3) 0.5738(3) 0.6950(2) 0.0560(7) Uani 1 1 d . . . . .
C003 C 0.7146(3) 0.5153(3) 0.6094(2) 0.0561(7) Uani 1 1 d . . . . .
C004 C 0.4193(4) 0.6627(3) 0.7449(3) 0.0635(8) Uani 1 1 d . . . . .
C005 C 0.5915(3) 0.5921(3) 0.6148(2) 0.0543(6) Uani 1 1 d . . . . .
C006 C 0.7620(4) 0.4697(3) 0.5189(3) 0.0655(8) Uani 1 1 d . . . . .
C007 C 0.4420(4) 0.4659(3) 0.7211(3) 0.0714(9) Uani 1 1 d . . . . .
C008 C 0.7872(4) 0.4849(3) 0.6969(3) 0.0683(9) Uani 1 1 d . . . . .
C009 C 0.5712(3) 0.6780(3) 0.5499(3) 0.0590(7) Uani 1 1 d . . . . .
H009 H 0.488377 0.719128 0.558628 0.071 Uiso 1 1 calc R U . . .
C00A C 0.3163(4) 0.6441(4) 0.8180(3) 0.0721(9) Uani 1 1 d . . . . .
C00B C 0.9517(4) 0.3704(3) 0.6026(4) 0.0749(10) Uani 1 1 d . . . . .
C00C C 0.9039(4) 0.4149(4) 0.6934(3) 0.0785(10) Uani 1 1 d . . . . .
C00D C 0.2745(4) 0.5370(4) 0.8435(3) 0.0742(10) Uani 1 1 d . . . . .
C00E C 0.8783(4) 0.3988(3) 0.5159(3) 0.0750(10) Uani 1 1 d . . . . .
C00F C 0.3390(5) 0.4482(4) 0.7945(4) 0.0819(11) Uani 1 1 d . . . . .
C00G C 0.5866(6) 0.8425(5) 0.4096(4) 0.1051(17) Uani 1 1 d . . . . .
H00B H 0.646144 0.886696 0.366185 0.158 Uiso 1 1 calc R U . . .
H00D H 0.558706 0.886976 0.466918 0.158 Uiso 1 1 calc R U . . .
H00G H 0.504002 0.819238 0.372933 0.158 Uiso 1 1 calc R U . . .
C00H C 1.0789(6) 0.2948(5) 0.5992(7) 0.1084(18) Uani 1 1 d . . . . .
H004 H 0.451(4) 0.735(3) 0.729(3) 0.068(10) Uiso 1 1 d . . . . .
H006 H 0.713(5) 0.487(4) 0.456(3) 0.090(13) Uiso 1 1 d . . . . .
H007 H 0.485(5) 0.402(4) 0.688(4) 0.100(15) Uiso 1 1 d . . . . .
H00A H 0.276(5) 0.708(4) 0.845(3) 0.084(13) Uiso 1 1 d . . . . .
H00H H 1.083(7) 0.240(6) 0.654(5) 0.14(2) Uiso 1 1 d . . . . .
H008 H 0.753(5) 0.510(4) 0.761(4) 0.097(14) Uiso 1 1 d . . . . .
H00E H 0.908(5) 0.370(4) 0.450(4) 0.097(14) Uiso 1 1 d . . . . .
H00I H 1.166(8) 0.331(7) 0.616(6) 0.16(3) Uiso 1 1 d . . . . .
H00J H 1.091(9) 0.253(7) 0.531(6) 0.17(3) Uiso 1 1 d . . . . .
H00F H 0.317(6) 0.371(5) 0.809(4) 0.118(17) Uiso 1 1 d . . . . .
H00C H 0.952(5) 0.393(4) 0.755(4) 0.099(15) Uiso 1 1 d . . . . .
C1 C 0.1612(5) 0.5165(5) 0.9222(4) 0.1080(17) Uani 1 1 d . . . . .
H1A H 0.162510 0.576479 0.970926 0.162 Uiso 1 1 calc R U . . .
H1B H 0.178798 0.446127 0.955624 0.162 Uiso 1 1 calc R U . . .
H1C H 0.070364 0.514030 0.889864 0.162 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
S001 C009 1.740(3) . ?
S001 C00G 1.782(4) . ?
C002 C004 1.389(5) . ?
C002 C005 1.482(4) . ?
C002 C007 1.385(5) . ?
C003 C005 1.481(4) . ?
C003 C006 1.388(4) . ?
C003 C008 1.393(5) . ?
C004 C00A 1.391(5) . ?
C004 H004 0.93(4) . ?
C005 C009 1.346(4) . ?
C006 C00E 1.386(5) . ?
C006 H006 0.98(4) . ?
C007 C00F 1.392(6) . ?
C007 H007 0.96(5) . ?
C008 C00C 1.382(5) . ?
C008 H008 0.95(5) . ?
C009 H009 0.9300 . ?
C00A C00D 1.373(6) . ?
C00A H00A 0.92(4) . ?
C00B C00C 1.388(6) . ?
C00B C00E 1.381(6) . ?
C00B C00H 1.502(6) . ?
C00C H00C 0.97(5) . ?
C00D C00F 1.379(6) . ?
C00D C1 1.514(5) . ?
C00E H00E 0.98(5) . ?
C00F H00F 0.96(6) . ?
C00G H00B 0.9600 . ?
C00G H00D 0.9600 . ?
C00G H00G 0.9600 . ?
C00H H00H 0.98(7) . ?
C00H H00I 0.96(8) . ?
C00H H00J 1.03(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C009 S001 C00G 99.98(19) . . ?
C004 C002 C005 122.1(3) . . ?
C007 C002 C004 117.1(3) . . ?
C007 C002 C005 120.8(3) . . ?
C006 C003 C005 122.4(3) . . ?
C006 C003 C008 117.1(3) . . ?
C008 C003 C005 120.5(3) . . ?
C002 C004 C00A 121.3(3) . . ?
C002 C004 H004 117(2) . . ?
C00A C004 H004 122(2) . . ?
C003 C005 C002 118.8(3) . . ?
C009 C005 C002 118.0(3) . . ?
C009 C005 C003 123.2(3) . . ?
C003 C006 H006 120(3) . . ?
C00E C006 C003 121.2(4) . . ?
C00E C006 H006 119(3) . . ?
C002 C007 C00F 121.1(4) . . ?
C002 C007 H007 120(3) . . ?
C00F C007 H007 119(3) . . ?
C003 C008 H008 119(3) . . ?
C00C C008 C003 121.5(4) . . ?
C00C C008 H008 119(3) . . ?
S001 C009 H009 116.1 . . ?
C005 C009 S001 127.9(2) . . ?
C005 C009 H009 116.1 . . ?
C004 C00A H00A 115(3) . . ?
C00D C00A C004 121.3(4) . . ?
C00D C00A H00A 123(3) . . ?
C00C C00B C00H 121.0(5) . . ?
C00E C00B C00C 117.5(4) . . ?
C00E C00B C00H 121.5(5) . . ?
C008 C00C C00B 121.1(4) . . ?
C008 C00C H00C 121(3) . . ?
C00B C00C H00C 118(3) . . ?
C00A C00D C00F 117.7(3) . . ?
C00A C00D C1 121.4(4) . . ?
C00F C00D C1 120.9(4) . . ?
C006 C00E H00E 118(3) . . ?
C00B C00E C006 121.6(4) . . ?
C00B C00E H00E 121(3) . . ?
C007 C00F H00F 116(3) . . ?
C00D C00F C007 121.4(4) . . ?
C00D C00F H00F 123(4) . . ?
S001 C00G H00B 109.5 . . ?
S001 C00G H00D 109.5 . . ?
S001 C00G H00G 109.5 . . ?
H00B C00G H00D 109.5 . . ?
H00B C00G H00G 109.5 . . ?
H00D C00G H00G 109.5 . . ?
C00B C00H H00H 114(4) . . ?
C00B C00H H00I 114(5) . . ?
C00B C00H H00J 113(5) . . ?
H00H C00H H00I 95(6) . . ?
H00H C00H H00J 109(6) . . ?
H00I C00H H00J 109(7) . . ?
C00D C1 H1A 109.5 . . ?
C00D C1 H1B 109.5 . . ?
C00D C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C002 C004 C00A C00D -0.3(6) . . . . ?
C002 C005 C009 S001 177.9(2) . . . . ?
C002 C007 C00F C00D 0.6(7) . . . . ?
C003 C005 C009 S001 -2.4(5) . . . . ?
C003 C006 C00E C00B 0.1(6) . . . . ?
C003 C008 C00C C00B -1.2(6) . . . . ?
C004 C002 C005 C003 141.9(3) . . . . ?
C004 C002 C005 C009 -38.4(5) . . . . ?
C004 C002 C007 C00F -0.4(6) . . . . ?
C004 C00A C00D C00F 0.4(6) . . . . ?
C004 C00A C00D C1 -179.3(4) . . . . ?
C005 C002 C004 C00A 178.2(3) . . . . ?
C005 C002 C007 C00F -178.4(4) . . . . ?
C005 C003 C006 C00E 179.4(3) . . . . ?
C005 C003 C008 C00C -178.8(4) . . . . ?
C006 C003 C005 C002 134.9(3) . . . . ?
C006 C003 C005 C009 -44.8(5) . . . . ?
C006 C003 C008 C00C 1.8(5) . . . . ?
C007 C002 C004 C00A 0.3(5) . . . . ?
C007 C002 C005 C003 -40.3(5) . . . . ?
C007 C002 C005 C009 139.4(4) . . . . ?
C008 C003 C005 C002 -44.4(4) . . . . ?
C008 C003 C005 C009 135.9(3) . . . . ?
C008 C003 C006 C00E -1.2(5) . . . . ?
C00A C00D C00F C007 -0.6(7) . . . . ?
C00C C00B C00E C006 0.5(6) . . . . ?
C00E C00B C00C C008 0.0(6) . . . . ?
C00G S001 C009 C005 -176.3(4) . . . . ?
C00H C00B C00C C008 179.7(4) . . . . ?
C00H C00B C00E C006 -179.2(4) . . . . ?
C1 C00D C00F C007 179.1(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.546
