# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cmrv-sh-ph_mo
_database_code_depnum_ccdc_archive 'CCDC 2072388'
loop_
_audit_author_name
_audit_author_address
'Mr. Darshan S. Mhatre'
;IIT Bombay
India
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;
_audit_creation_date             2020-08-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H27 N O4 S'
_chemical_formula_sum            'C31 H27 N O4 S'
_chemical_formula_weight         509.59
_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                   14.2727(6)
_cell_length_b                   9.0999(4)
_cell_length_c                   20.3049(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.367(4)
_cell_angle_gamma                90
_cell_volume                     2585.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10696
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.6240
_cell_measurement_theta_min      2.0560
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.265
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  25.00   1.00    8.00    --  -20.00   0.00 -36.00  103
  2  ω    -50.00  70.00   1.00    8.00    --  -20.00  72.00 -36.00  120
  3  ω    -54.00  -4.00   1.00    8.00    --  -20.00  72.00-108.00   50
  4  ω    -60.00 -30.00   1.00    8.00    --  -20.00 -72.00-180.00   30
  5  ω   -110.00  70.00   1.00    8.00    --  -20.00   0.00-108.00  180
  6  ω    -72.00 -18.00   1.00    8.00    --  -20.00 -72.00-108.00   54
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0259304000
_diffrn_orient_matrix_UB_12      -0.0254447000
_diffrn_orient_matrix_UB_13      0.0241704000
_diffrn_orient_matrix_UB_21      -0.0066461000
_diffrn_orient_matrix_UB_22      -0.0689520000
_diffrn_orient_matrix_UB_23      -0.0165439000
_diffrn_orient_matrix_UB_31      0.0430645000
_diffrn_orient_matrix_UB_32      -0.0259786000
_diffrn_orient_matrix_UB_33      0.0202653000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3497
_reflns_number_total             4557
_reflns_odcompleteness_completeness 92.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.11
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+1.6822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C4(H4), C3(H3), C17(H17), C7(H7), C30(H30), C12(H12),
 C11(H11), C6(H6), C31(H31), C29(H29), C27(H27), C18(H18), C20(H20), C21(H21),
 C28(H28), C19(H19)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S01 S 0.03229(4) 0.70025(7) 0.57358(3) 0.02175(18) Uani 1 1 d . . . . .
O1 O 0.02390(12) 0.7499(2) 0.63862(9) 0.0300(4) Uani 1 1 d . . . . .
O3 O 0.23029(12) 0.68459(19) 0.65559(8) 0.0264(4) Uani 1 1 d . . . . .
O2 O -0.04958(11) 0.63726(19) 0.53025(9) 0.0272(4) Uani 1 1 d . . . . .
O4 O 0.23788(12) 0.6129(2) 0.48733(9) 0.0338(5) Uani 1 1 d . . . . .
N1 N 0.11355(13) 0.5670(2) 0.58077(10) 0.0205(5) Uani 1 1 d . . . . .
H1 H 0.096552 0.480333 0.563179 0.025 Uiso 1 1 calc R . . . .
C10 C 0.29810(16) 0.5143(3) 0.52648(12) 0.0230(6) Uani 1 1 d . . . . .
C13 C 0.41222(17) 0.3215(3) 0.61175(13) 0.0263(6) Uani 1 1 d . . . . .
H13 H 0.451952 0.254804 0.640600 0.032 Uiso 1 1 calc R . . . .
C14 C 0.33857(16) 0.3942(3) 0.63478(12) 0.0210(5) Uani 1 1 d . . . . .
C4 C 0.06388(17) 0.8362(3) 0.46055(13) 0.0242(6) Uani 1 1 d . . . . .
H4 H 0.022548 0.764477 0.436249 0.029 Uiso 1 1 calc R . . . .
C26 C 0.26410(18) 0.6685(3) 0.42917(13) 0.0273(6) Uani 1 1 d . . . . .
C15 C 0.32190(17) 0.3648(3) 0.70384(12) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.28053(16) 0.4914(3) 0.59105(12) 0.0195(5) Uani 1 1 d . . . . .
C3 C 0.10886(17) 0.9392(3) 0.42703(13) 0.0267(6) Uani 1 1 d . . . . .
H3 H 0.097660 0.937575 0.379338 0.032 Uiso 1 1 calc R . . . .
C5 C 0.08040(16) 0.8398(3) 0.53039(12) 0.0211(5) Uani 1 1 d . . . . .
C8 C 0.20776(16) 0.5888(3) 0.61387(12) 0.0206(5) Uani 1 1 d . . . . .
C17 C 0.48691(18) 0.4485(3) 0.75906(13) 0.0291(6) Uani 1 1 d . . . . .
H17 H 0.486372 0.513446 0.722340 0.035 Uiso 1 1 calc R . . . .
C23 C 0.14839(17) 0.3168(3) 0.72397(12) 0.0239(6) Uani 1 1 d . . . . .
C7 C 0.18399(18) 1.0473(3) 0.53138(14) 0.0314(6) Uani 1 1 d . . . . .
H7 H 0.224261 1.120465 0.555499 0.038 Uiso 1 1 calc R . . . .
C30 C 0.35030(18) 0.8416(3) 0.37632(14) 0.0291(6) Uani 1 1 d . . . . .
H30 H 0.396318 0.917990 0.379307 0.035 Uiso 1 1 calc R . . . .
C12 C 0.42805(18) 0.3454(3) 0.54764(13) 0.0281(6) Uani 1 1 d . . . . .
H12 H 0.478302 0.294460 0.532969 0.034 Uiso 1 1 calc R . . . .
C11 C 0.37162(17) 0.4428(3) 0.50431(13) 0.0263(6) Uani 1 1 d . . . . .
H11 H 0.383239 0.459947 0.460462 0.032 Uiso 1 1 calc R . . . .
C6 C 0.14031(18) 0.9452(3) 0.56615(14) 0.0284(6) Uani 1 1 d . . . . .
H6 H 0.151200 0.947216 0.613827 0.034 Uiso 1 1 calc R . . . .
C31 C 0.33006(17) 0.7806(3) 0.43463(13) 0.0277(6) Uani 1 1 d . . . . .
H31 H 0.361105 0.815576 0.477486 0.033 Uiso 1 1 calc R . . . .
C16 C 0.40722(17) 0.3601(3) 0.76052(12) 0.0220(5) Uani 1 1 d . . . . .
C29 C 0.3045(2) 0.7926(3) 0.31447(14) 0.0355(7) Uani 1 1 d . . . . .
H29 H 0.318757 0.834887 0.274805 0.043 Uiso 1 1 calc R . . . .
C2 C 0.16947(17) 1.0438(3) 0.46139(14) 0.0273(6) Uani 1 1 d . . . . .
C22 C 0.23488(17) 0.3425(3) 0.71450(12) 0.0228(6) Uani 1 1 d . . . . .
C27 C 0.2172(2) 0.6173(3) 0.36759(14) 0.0358(7) Uani 1 1 d . . . . .
H27 H 0.171968 0.539860 0.364550 0.043 Uiso 1 1 calc R . . . .
C18 C 0.56646(19) 0.4427(3) 0.81038(14) 0.0346(7) Uani 1 1 d . . . . .
H18 H 0.619987 0.503691 0.808765 0.042 Uiso 1 1 calc R . . . .
C25 C 0.1096(2) 0.1627(3) 0.72382(14) 0.0357(7) Uani 1 1 d . . . . .
H25A H 0.054756 0.151712 0.686628 0.054 Uiso 1 1 calc GR . . . .
H25B H 0.089426 0.143753 0.766453 0.054 Uiso 1 1 calc GR . . . .
H25C H 0.159492 0.092328 0.718287 0.054 Uiso 1 1 calc GR . . . .
C20 C 0.48969(19) 0.2615(3) 0.86647(13) 0.0340(7) Uani 1 1 d . . . . .
H20 H 0.490503 0.197371 0.903515 0.041 Uiso 1 1 calc R . . . .
C24 C 0.08130(18) 0.4378(3) 0.73533(14) 0.0317(6) Uani 1 1 d . . . . .
H24A H 0.115170 0.532080 0.739176 0.048 Uiso 1 1 calc GR . . . .
H24B H 0.058103 0.418531 0.776829 0.048 Uiso 1 1 calc GR . . . .
H24C H 0.026986 0.441603 0.697384 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.40966(18) 0.2670(3) 0.81530(13) 0.0268(6) Uani 1 1 d . . . . .
H21 H 0.355993 0.206850 0.817587 0.032 Uiso 1 1 calc R . . . .
C28 C 0.2378(2) 0.6818(3) 0.31002(14) 0.0435(8) Uani 1 1 d . . . . .
H28 H 0.205432 0.649117 0.267105 0.052 Uiso 1 1 calc R . . . .
C1 C 0.21952(19) 1.1522(3) 0.42369(16) 0.0367(7) Uani 1 1 d . . . . .
H1A H 0.206156 1.127422 0.375787 0.055 Uiso 1 1 calc GR . . . .
H1B H 0.288573 1.147864 0.441076 0.055 Uiso 1 1 calc GR . . . .
H1C H 0.196279 1.251672 0.429779 0.055 Uiso 1 1 calc GR . . . .
C19 C 0.56839(19) 0.3484(3) 0.86409(14) 0.0338(7) Uani 1 1 d . . . . .
H19 H 0.623376 0.343411 0.899063 0.041 Uiso 1 1 calc R . . . .


_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
S01 O1 1.4230(18) . ?
S01 O2 1.4363(18) . ?
S01 N1 1.6642(19) . ?
S01 C5 1.758(3) . ?
O3 C8 1.214(3) . ?
O4 C10 1.381(3) . ?
O4 C26 1.402(3) . ?
N1 C8 1.394(3) . ?
C10 C9 1.398(3) . ?
C10 C11 1.383(3) . ?
C13 C14 1.398(3) . ?
C13 C12 1.382(4) . ?
C14 C15 1.492(3) . ?
C14 C9 1.403(3) . ?
C4 C3 1.388(4) . ?
C4 C5 1.391(4) . ?
C26 C31 1.378(4) . ?
C26 C27 1.378(4) . ?
C15 C16 1.502(3) . ?
C15 C22 1.318(3) . ?
C9 C8 1.506(3) . ?
C3 C2 1.380(4) . ?
C5 C6 1.390(3) . ?
C17 C16 1.398(3) . ?
C17 C18 1.383(4) . ?
C23 C22 1.307(3) . ?
C23 C25 1.508(4) . ?
C23 C24 1.507(4) . ?
C7 C6 1.387(4) . ?
C7 C2 1.396(4) . ?
C30 C31 1.389(4) . ?
C30 C29 1.371(4) . ?
C12 C11 1.389(4) . ?
C16 C21 1.393(3) . ?
C29 C28 1.377(4) . ?
C2 C1 1.512(4) . ?
C27 C28 1.390(4) . ?
C18 C19 1.384(4) . ?
C20 C21 1.385(4) . ?
C20 C19 1.382(4) . ?

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
O1 S01 O2 119.22(11) . . ?
O1 S01 N1 109.55(10) . . ?
O1 S01 C5 110.24(12) . . ?
O2 S01 N1 103.40(10) . . ?
O2 S01 C5 109.47(11) . . ?
N1 S01 C5 103.66(10) . . ?
C10 O4 C26 118.71(18) . . ?
C8 N1 S01 121.88(17) . . ?
O4 C10 C9 115.5(2) . . ?
O4 C10 C11 123.0(2) . . ?
C11 C10 C9 121.5(2) . . ?
C12 C13 C14 120.9(2) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 C9 118.4(2) . . ?
C9 C14 C15 121.6(2) . . ?
C3 C4 C5 118.8(2) . . ?
C31 C26 O4 119.4(2) . . ?
C27 C26 O4 118.7(3) . . ?
C27 C26 C31 121.7(2) . . ?
C14 C15 C16 118.0(2) . . ?
C22 C15 C14 120.8(2) . . ?
C22 C15 C16 121.2(2) . . ?
C10 C9 C14 119.7(2) . . ?
C10 C9 C8 117.6(2) . . ?
C14 C9 C8 122.2(2) . . ?
C2 C3 C4 121.5(2) . . ?
C4 C5 S01 119.12(19) . . ?
C6 C5 S01 119.9(2) . . ?
C6 C5 C4 120.8(2) . . ?
O3 C8 N1 122.4(2) . . ?
O3 C8 C9 122.2(2) . . ?
N1 C8 C9 115.2(2) . . ?
C18 C17 C16 120.8(2) . . ?
C22 C23 C25 121.5(2) . . ?
C22 C23 C24 122.6(2) . . ?
C24 C23 C25 115.9(2) . . ?
C6 C7 C2 120.8(2) . . ?
C29 C30 C31 120.6(3) . . ?
C13 C12 C11 121.0(2) . . ?
C10 C11 C12 118.4(2) . . ?
C7 C6 C5 119.2(3) . . ?
C26 C31 C30 118.7(2) . . ?
C17 C16 C15 120.5(2) . . ?
C21 C16 C15 121.2(2) . . ?
C21 C16 C17 118.3(2) . . ?
C30 C29 C28 119.8(3) . . ?
C3 C2 C7 118.9(2) . . ?
C3 C2 C1 120.4(3) . . ?
C7 C2 C1 120.7(2) . . ?
C23 C22 C15 178.3(3) . . ?
C26 C27 C28 118.4(3) . . ?
C17 C18 C19 120.2(3) . . ?
C19 C20 C21 120.6(3) . . ?
C20 C21 C16 120.5(2) . . ?
C29 C28 C27 120.8(3) . . ?
C20 C19 C18 119.5(2) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.744
