# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_pm_am_958_auto
_database_code_depnum_ccdc_archive 'CCDC 2205394'
loop_
_audit_author_name
_audit_author_address
'Mr. Ashis'
;NISER
India
;
_audit_update_record             
;
2022-09-05 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_audit_creation_date             2022-09-05
_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         'C15 H12 F4 O3 S'
_chemical_formula_sum            'C15 H12 F4 O3 S'
_chemical_formula_weight         348.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         ' C H S O F'
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9500(4)
_cell_length_b                   9.8071(6)
_cell_length_c                   11.6221(5)
_cell_angle_alpha                90.667(4)
_cell_angle_beta                 105.074(4)
_cell_angle_gamma                107.794(5)
_cell_volume                     724.72(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8873
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.5420
_cell_measurement_theta_min      3.6300
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.799
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13243
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_min         3.649
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.799
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  38.00   0.50    2.88    --    3.51 -96.00  43.00  112
  2  ω    -18.00  30.00   0.50    2.88    --   -4.29 -96.00  43.00   96
  3  ω    -15.00  39.00   0.50    2.88    --    3.51 -99.00   0.00  108
  4  ω    -59.00  15.00   0.50    2.88    --    3.51 -57.00-150.00  148
  5  ω    -42.00  19.00   0.50    2.88    --   -4.29 -77.00 -60.00  122
  6  ω    -38.00  19.00   0.50    2.88    --   -4.29 -77.00 120.00  114
  7  ω    -24.00  18.00   0.50    2.88    --   -4.29  77.00  60.00   84
  8  ω    -15.00  14.00   0.50    2.88    --   -4.29  77.00 150.00   58
  9  ω     -4.00  59.00   0.50    2.88    --   -4.29  37.00 150.00  126
 10  ω      6.00  32.00   0.50    2.88    --   -4.29 -99.00 150.00   52
 11  ω    -15.00  10.00   0.50    2.88    --   -4.29 -99.00  60.00   50
 12  ω    -27.00  18.00   0.50    2.88    --   -4.29  77.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0595442000
_diffrn_orient_matrix_UB_12      0.0446814000
_diffrn_orient_matrix_UB_13      0.0082814000
_diffrn_orient_matrix_UB_21      -0.0667584000
_diffrn_orient_matrix_UB_22      -0.0234515000
_diffrn_orient_matrix_UB_23      -0.0589326000
_diffrn_orient_matrix_UB_31      -0.0666356000
_diffrn_orient_matrix_UB_32      -0.0572763000
_diffrn_orient_matrix_UB_33      0.0222009000
_diffrn_oxdiff_digest_frames     
;
010f8604dbf567c50d3375236234ae775f000255a02
;
_diffrn_oxdiff_digest_hkl        
;
012f0455775ee4c313bd00b10df488c91c24d5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3138
_reflns_number_total             3515
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_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         0.356
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      0.992
_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)+(0.0391P)²+0.3655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0827
_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:
 C00H(H00H), C00J(H00J), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00B,H00C), C00L(H00D,H00E,H00F), C00N(H00G,H00I,H00K)
;
_atom_sites_solution_hydrogens   geom
_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 0.26754(5) 0.66545(3) 0.75706(3) 0.01281(9) Uani 1 1 d . . . . .
F002 F 0.11564(13) 0.33954(8) 0.75659(7) 0.02202(18) Uani 1 1 d . . . . .
F003 F 0.35082(12) 0.70944(8) 0.51826(7) 0.01883(17) Uani 1 1 d . . . . .
F004 F 0.29380(13) 0.51271(10) 0.34298(7) 0.0256(2) Uani 1 1 d . . . . .
F005 F 0.06746(14) 0.14304(9) 0.58184(8) 0.0285(2) Uani 1 1 d . . . . .
O006 O 0.56956(13) 0.52814(9) 0.87591(8) 0.01420(19) Uani 1 1 d . . . . .
O007 O 1.19410(14) 0.91904(10) 0.91557(9) 0.01706(19) Uani 1 1 d . . . . .
O008 O 0.50825(14) 0.95384(10) 0.71666(9) 0.0177(2) Uani 1 1 d . . . . .
C009 C 0.67291(19) 0.66526(13) 0.85995(10) 0.0121(2) Uani 1 1 d . . . . .
C00A C 0.6400(2) 0.88434(13) 0.77609(11) 0.0133(2) Uani 1 1 d . . . . .
C00B C 0.54459(19) 0.74348(13) 0.79942(11) 0.0121(2) Uani 1 1 d . . . . .
C00C C 0.28066(19) 0.56995(13) 0.53623(11) 0.0144(2) Uani 1 1 d . . . . .
C00D C 0.23742(18) 0.53188(13) 0.64389(11) 0.0133(2) Uani 1 1 d . . . . .
C00E C 0.16413(19) 0.38533(14) 0.65590(12) 0.0158(3) Uani 1 1 d . . . . .
C00F C 0.98058(19) 0.86805(13) 0.87449(11) 0.0138(2) Uani 1 1 d . . . . .
C00G C 0.6939(2) 0.44373(13) 0.93427(12) 0.0173(3) Uani 1 1 d . . . . .
H00A H 0.790766 0.436258 0.888274 0.026 Uiso 1 1 calc GR . . . .
H00B H 0.601785 0.347282 0.939582 0.026 Uiso 1 1 calc GR . . . .
H00C H 0.774630 0.489720 1.015015 0.026 Uiso 1 1 calc GR . . . .
C00H C 0.8587(2) 0.94783(13) 0.81328(11) 0.0148(2) Uani 1 1 d . . . . .
H00H H 0.922655 1.043290 0.797128 0.018 Uiso 1 1 calc R . . . .
C00I C 0.2529(2) 0.46739(15) 0.44590(11) 0.0179(3) Uani 1 1 d . . . . .
C00J C 0.88999(19) 0.72700(13) 0.89781(11) 0.0134(2) Uani 1 1 d . . . . .
H00J H 0.975785 0.673956 0.939047 0.016 Uiso 1 1 calc R . . . .
C00K C 0.1379(2) 0.28371(14) 0.56473(13) 0.0193(3) Uani 1 1 d . . . . .
C00L C 1.2963(2) 1.06395(14) 0.89602(13) 0.0186(3) Uani 1 1 d . . . . .
H00D H 1.264540 1.073441 0.809832 0.028 Uiso 1 1 calc GR . . . .
H00E H 1.448588 1.087793 0.929934 0.028 Uiso 1 1 calc GR . . . .
H00F H 1.245558 1.129793 0.934895 0.028 Uiso 1 1 calc GR . . . .
C00M C 0.1814(2) 0.32239(15) 0.45819(12) 0.0201(3) Uani 1 1 d . . . . .
H00M H 0.162987 0.252001 0.395935 0.024 Uiso 1 1 calc R . . . .
C00N C 0.5985(2) 1.09065(16) 0.67854(16) 0.0295(3) Uani 1 1 d . . . . .
H00G H 0.689190 1.081593 0.628870 0.044 Uiso 1 1 calc GR . . . .
H00I H 0.682185 1.159499 0.748767 0.044 Uiso 1 1 calc GR . . . .
H00K H 0.486262 1.124877 0.631809 0.044 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 C00B 1.7701(12) . ?
S001 C00D 1.7717(12) . ?
F002 C00E 1.3452(15) . ?
F003 C00C 1.3434(14) . ?
F004 C00I 1.3495(15) . ?
F005 C00K 1.3516(15) . ?
O006 C009 1.3577(14) . ?
O006 C00G 1.4276(15) . ?
O007 C00F 1.3611(15) . ?
O007 C00L 1.4318(15) . ?
O008 C00A 1.3576(15) . ?
O008 C00N 1.4262(16) . ?
C009 C00B 1.4082(17) . ?
C009 C00J 1.3880(17) . ?
C00A C00B 1.4013(17) . ?
C00A C00H 1.3995(18) . ?
C00C C00D 1.3903(18) . ?
C00C C00I 1.3793(18) . ?
C00D C00E 1.3924(18) . ?
C00E C00K 1.3830(19) . ?
C00F C00H 1.3930(18) . ?
C00F C00J 1.3960(17) . ?
C00I C00M 1.378(2) . ?
C00K C00M 1.380(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
C00B S001 C00D 99.70(6) . . ?
C009 O006 C00G 117.30(10) . . ?
C00F O007 C00L 117.36(10) . . ?
C00A O008 C00N 118.11(11) . . ?
O006 C009 C00B 115.42(11) . . ?
O006 C009 C00J 123.80(11) . . ?
C00J C009 C00B 120.77(11) . . ?
O008 C00A C00B 116.14(11) . . ?
O008 C00A C00H 122.85(11) . . ?
C00H C00A C00B 121.01(11) . . ?
C009 C00B S001 120.12(9) . . ?
C00A C00B S001 121.00(9) . . ?
C00A C00B C009 118.86(11) . . ?
F003 C00C C00D 119.97(11) . . ?
F003 C00C C00I 118.47(11) . . ?
C00I C00C C00D 121.56(12) . . ?
C00C C00D S001 120.75(10) . . ?
C00C C00D C00E 116.78(11) . . ?
C00E C00D S001 122.44(10) . . ?
F002 C00E C00D 120.48(11) . . ?
F002 C00E C00K 118.51(12) . . ?
C00K C00E C00D 121.01(12) . . ?
O007 C00F C00H 123.68(11) . . ?
O007 C00F C00J 114.68(11) . . ?
C00H C00F C00J 121.64(12) . . ?
C00F C00H C00A 118.58(11) . . ?
F004 C00I C00C 118.09(12) . . ?
F004 C00I C00M 120.31(12) . . ?
C00M C00I C00C 121.58(12) . . ?
C009 C00J C00F 119.12(11) . . ?
F005 C00K C00E 118.34(12) . . ?
F005 C00K C00M 119.81(12) . . ?
C00M C00K C00E 121.85(12) . . ?
C00I C00M C00K 117.21(12) . . ?

_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.645
