# Electronic Supplementary Material (ESI) for ChemComm.
# 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_HD4OMETPY_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2252567'
loop_
_audit_author_name
_audit_author_address
'Hirendra n.hirendra'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 N2 O S'
_chemical_formula_weight         394.47

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   8.3336(4)
_cell_length_b                   18.5187(9)
_cell_length_c                   26.3322(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4063.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.67

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            84726
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3558
_reflns_number_gt                2882
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0957P)²+1.5157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3558
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1740
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_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 0.28859(9) 0.27750(4) 0.51364(2) 0.0703(3) Uani 1 1 d . . . . .
N1 N 0.5181(2) 0.37407(10) 0.49358(6) 0.0517(5) Uani 1 1 d . . . . .
O1 O 0.2648(3) 0.31221(12) 0.29089(7) 0.0799(6) Uani 1 1 d . . . . .
C2 C 0.4625(3) 0.35599(12) 0.58220(8) 0.0491(5) Uani 1 1 d . . . . .
C3 C 0.5815(3) 0.40565(11) 0.59595(8) 0.0467(5) Uani 1 1 d . . . . .
N2 N 0.2807(3) 0.29106(16) 0.64671(9) 0.0822(8) Uani 1 1 d . . . . .
C1 C 0.4377(3) 0.34194(12) 0.53029(8) 0.0512(5) Uani 1 1 d . . . . .
C5 C 0.6310(3) 0.42276(12) 0.50630(8) 0.0473(5) Uani 1 1 d . . . . .
C19 C 0.1575(3) 0.32227(14) 0.42348(9) 0.0596(6) Uani 1 1 d . . . . .
H19 H 0.074270 0.341150 0.442908 0.071 Uiso 1 1 calc R U . . .
C18 C 0.2831(3) 0.28671(13) 0.44701(10) 0.0573(6) Uani 1 1 d . . . . .
C4 C 0.6646(3) 0.43908(12) 0.55666(8) 0.0513(5) Uani 1 1 d . . . . .
H4 H 0.743796 0.472807 0.564209 0.062 Uiso 1 1 calc R U . . .
C25 C 0.3629(3) 0.32025(14) 0.61894(9) 0.0589(6) Uani 1 1 d . . . . .
C11 C 0.8142(3) 0.51648(15) 0.46952(10) 0.0613(6) Uani 1 1 d . . . . .
H11 H 0.821585 0.538209 0.501280 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6260(3) 0.42187(12) 0.64936(8) 0.0505(5) Uani 1 1 d . . . . .
C20 C 0.1549(3) 0.32989(13) 0.37145(10) 0.0621(6) Uani 1 1 d . . . . .
H20 H 0.069504 0.353479 0.355922 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7204(3) 0.45545(13) 0.46339(9) 0.0518(6) Uani 1 1 d . . . . .
C23 C 0.4032(3) 0.25829(16) 0.41712(10) 0.0714(7) Uani 1 1 d . . . . .
H23 H 0.486506 0.232952 0.432426 0.086 Uiso 1 1 calc R U . . .
C13 C 0.6372(3) 0.36774(14) 0.68538(9) 0.0629(6) Uani 1 1 d . . . . .
H13 H 0.606937 0.320925 0.676934 0.075 Uiso 1 1 calc R U . . .
C10 C 0.8975(3) 0.54555(17) 0.42871(12) 0.0740(8) Uani 1 1 d . . . . .
H10 H 0.960391 0.586510 0.433295 0.089 Uiso 1 1 calc R U . . .
C21 C 0.2786(3) 0.30267(14) 0.34221(9) 0.0599(6) Uani 1 1 d . . . . .
C22 C 0.4029(3) 0.26649(16) 0.36512(10) 0.0719(8) Uani 1 1 d . . . . .
H22 H 0.486163 0.247676 0.345694 0.086 Uiso 1 1 calc R U . . .
C8 C 0.7949(4) 0.45389(19) 0.37494(11) 0.0812(9) Uani 1 1 d . . . . .
H8 H 0.788124 0.432619 0.343016 0.097 Uiso 1 1 calc R U . . .
C7 C 0.7114(3) 0.42428(16) 0.41531(9) 0.0682(7) Uani 1 1 d . . . . .
H7 H 0.648893 0.383289 0.410312 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8874(3) 0.51412(19) 0.38157(12) 0.0813(9) Uani 1 1 d . . . . .
H9 H 0.943170 0.533749 0.354275 0.098 Uiso 1 1 calc R U . . .
C17 C 0.6682(4) 0.49135(15) 0.66360(10) 0.0697(7) Uani 1 1 d . . . . .
H17 H 0.657770 0.529023 0.640479 0.084 Uiso 1 1 calc R U . . .
C14 C 0.6930(4) 0.38235(17) 0.73387(10) 0.0792(8) Uani 1 1 d . . . . .
H14 H 0.698582 0.345545 0.757833 0.095 Uiso 1 1 calc R U . . .
C15 C 0.7396(4) 0.45038(18) 0.74649(11) 0.0852(9) Uani 1 1 d . . . . .
H15 H 0.780758 0.459654 0.778662 0.102 Uiso 1 1 calc R U . . .
C16 C 0.7259(4) 0.50521(18) 0.71197(11) 0.0856(9) Uani 1 1 d . . . . .
H16 H 0.755416 0.551918 0.720984 0.103 Uiso 1 1 calc R U . . .
C24 C 0.4027(5) 0.2984(2) 0.26048(12) 0.1124(12) Uani 1 1 d . . . . .
H24A H 0.489985 0.328123 0.271863 0.169 Uiso 1 1 calc R U . . .
H24B H 0.378974 0.309359 0.225647 0.169 Uiso 1 1 calc R U . . .
H24C H 0.432096 0.248473 0.263439 0.169 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 C18 1.763(3) . ?
S1 C1 1.778(2) . ?
N1 C1 1.318(3) . ?
N1 C5 1.345(3) . ?
O1 C21 1.368(3) . ?
O1 C24 1.423(4) . ?
C2 C3 1.400(3) . ?
C2 C1 1.407(3) . ?
C2 C25 1.436(3) . ?
C3 C4 1.391(3) . ?
C3 C12 1.485(3) . ?
N2 C25 1.139(3) . ?
C5 C4 1.388(3) . ?
C5 C6 1.483(3) . ?
C19 C20 1.378(3) . ?
C19 C18 1.383(3) . ?
C18 C23 1.378(4) . ?
C11 C6 1.384(3) . ?
C11 C10 1.388(4) . ?
C12 C17 1.386(3) . ?
C12 C13 1.383(3) . ?
C20 C21 1.382(4) . ?
C6 C7 1.393(4) . ?
C23 C22 1.378(4) . ?
C13 C14 1.386(4) . ?
C10 C9 1.374(4) . ?
C21 C22 1.373(4) . ?
C8 C9 1.367(5) . ?
C8 C7 1.384(4) . ?
C17 C16 1.385(4) . ?
C14 C15 1.360(4) . ?
C15 C16 1.368(5) . ?

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
C18 S1 C1 101.46(11) . . ?
C1 N1 C5 118.40(19) . . ?
C21 O1 C24 117.7(2) . . ?
C3 C2 C1 118.48(19) . . ?
C3 C2 C25 122.53(19) . . ?
C1 C2 C25 119.0(2) . . ?
C4 C3 C2 116.93(19) . . ?
C4 C3 C12 119.3(2) . . ?
C2 C3 C12 123.70(19) . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 S1 118.53(16) . . ?
C2 C1 S1 117.81(17) . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 115.78(19) . . ?
C4 C5 C6 122.5(2) . . ?
C20 C19 C18 120.4(2) . . ?
C23 C18 C19 118.4(2) . . ?
C23 C18 S1 120.8(2) . . ?
C19 C18 S1 120.77(19) . . ?
C3 C4 C5 120.9(2) . . ?
N2 C25 C2 177.6(3) . . ?
C6 C11 C10 120.6(3) . . ?
C17 C12 C13 118.0(2) . . ?
C17 C12 C3 120.5(2) . . ?
C13 C12 C3 121.3(2) . . ?
C19 C20 C21 120.4(2) . . ?
C11 C6 C7 118.3(2) . . ?
C11 C6 C5 121.9(2) . . ?
C7 C6 C5 119.8(2) . . ?
C22 C23 C18 121.6(2) . . ?
C14 C13 C12 120.9(2) . . ?
C9 C10 C11 120.3(3) . . ?
O1 C21 C22 124.1(2) . . ?
O1 C21 C20 116.2(2) . . ?
C22 C21 C20 119.7(2) . . ?
C21 C22 C23 119.5(2) . . ?
C9 C8 C7 120.6(3) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C9 C10 119.7(3) . . ?
C12 C17 C16 120.6(3) . . ?
C15 C14 C13 120.1(3) . . ?
C14 C15 C16 120.1(3) . . ?
C15 C16 C17 120.2(3) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.134



