# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_wtl-zhk-1
_database_code_depnum_ccdc_archive 'CCDC 1935757'
loop_
_audit_author_name
_audit_author_address
'Chen Yuan'
;Sichuan University
China
;
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C25 H29 F N2 P S'
_chemical_formula_sum            'C25 H29 F I N2 P S'
_chemical_formula_weight         566.43
_chemical_absolute_configuration ad
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.4752(4)
_cell_length_b                   11.6241(3)
_cell_length_c                   12.9271(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.550(5)
_cell_angle_gamma                90
_cell_volume                     1324.26(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4293
_cell_measurement_temperature    295.4(6)
_cell_measurement_theta_max      71.5140
_cell_measurement_theta_min      3.6980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6569
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        65.508
_diffrn_reflns_theta_max         65.508
_diffrn_reflns_theta_min         3.676
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.4(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.32    --  -36.04  57.00-150.00   84
  2  ω   -104.00  -9.00   1.00    1.32    --  -36.04 -77.00 120.00   95
  3  ω   -105.00 -50.00   1.00    1.32    --  -36.04-159.00 159.00   55
  4  ω      1.00  75.00   1.00    1.32    --   36.04 -99.00-120.00   74
  5  ω     23.00  89.00   1.00    1.32    --   36.04-125.00  90.00   66
  6  ω     37.00 109.00   1.00    7.00    --  106.21 -94.00 -30.00   72
  7  ω     36.00 128.00   1.00    7.00    --  106.21 -30.00-120.00   92
  8  ω     85.00 176.00   1.00    7.00    --  106.21  30.00-150.00   91
  9  ω     37.00 109.00   1.00    7.00    --  106.21 -94.00 -60.00   72
 10  ω     36.00 128.00   1.00    7.00    --  106.21 -30.00 -30.00   92
 11  ω     85.00 176.00   1.00    7.00    --  106.21  30.00 -60.00   91
 12  ω    100.00 176.00   1.00    7.00    --  106.21 111.00  30.00   76
 13  ω     36.00 113.00   1.00    7.00    --  106.21-111.00 120.00   77
 14  ω     39.00 133.00   1.00    7.00    --  106.21 -77.00 120.00   94
 15  ω   -104.00 -66.00   1.00    1.32    --  -36.04 -77.00-120.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0486373000
_diffrn_orient_matrix_UB_12      -0.0159361000
_diffrn_orient_matrix_UB_13      0.1266660000
_diffrn_orient_matrix_UB_21      -0.1637497000
_diffrn_orient_matrix_UB_22      0.0239375000
_diffrn_orient_matrix_UB_23      -0.0085552000
_diffrn_orient_matrix_UB_31      -0.0364175000
_diffrn_orient_matrix_UB_32      -0.1294282000
_diffrn_orient_matrix_UB_33      -0.0172600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.388
_reflns_Friedel_fraction_full    0.432
_reflns_Friedel_fraction_max     0.432
_reflns_number_gt                3172
_reflns_number_total             3343
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.878
_refine_diff_density_min         -2.256
_refine_diff_density_rms         0.266
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.009(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      1.131
_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)+(0.1668P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C12(H12), N13(H13), C16(H16), C18(H18), C19(H19), C20(H20), C22(H22),
 C33(H33), C39(H39), C0AA(H0AA), C11(H11), C9(H9), C1AA(H1AA), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C49(H49A,H49B,H49C), C2AA(H2AA,H2AB,H2AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.16652(8) 0.82782(9) 0.43774(6) 0.0426(4) Uani 1 1 d . . . . .
P2 P -0.3562(4) 0.6976(3) 0.4296(2) 0.0235(7) Uani 1 1 d . . . . .
S3 S -0.3744(4) 0.7419(4) 0.0336(3) 0.0447(10) Uani 1 1 d . . . . .
N4 N -0.1785(13) 0.7145(11) 0.2418(9) 0.031(2) Uani 1 1 d . . . . .
H4 H -0.0985 0.7376 0.2953 0.038 Uiso 1 1 calc R . . . .
C6 C -0.2547(14) 0.6152(12) 0.2644(9) 0.027(3) Uani 1 1 d . . . . .
H6 H -0.3642 0.6239 0.2241 0.032 Uiso 1 1 calc R . . . .
C7 C -0.2841(17) 0.7156(12) 0.5778(11) 0.030(3) Uani 1 1 d . . . . .
C10 C -0.3866(14) 0.8378(12) 0.3660(10) 0.027(2) Uani 1 1 d . . . . .
C12 C -0.0214(17) 0.9681(15) 0.0338(13) 0.039(3) Uani 1 1 d . . . . .
H12 H 0.0643 0.9215 0.0591 0.046 Uiso 1 1 calc R . . . .
N13 N -0.1222(15) 0.8597(13) 0.1500(11) 0.048(4) Uani 1 1 d . . . . .
H13 H -0.0403 0.8641 0.2080 0.057 Uiso 1 1 calc R . . . .
C14 C -0.1411(14) 0.9438(14) 0.0668(9) 0.026(3) Uani 1 1 d . . . . .
C15 C -0.2229(15) 0.6129(11) 0.3905(9) 0.024(3) Uani 1 1 d . . . . .
H15A H -0.1212 0.6417 0.4303 0.029 Uiso 1 1 calc R . . . .
H15B H -0.2264 0.5338 0.4135 0.029 Uiso 1 1 calc R . . . .
C16 C -0.1500(19) 0.6651(16) 0.6445(11) 0.042(4) Uani 1 1 d . . . . .
H16 H -0.0955 0.6196 0.6132 0.051 Uiso 1 1 calc R . . . .
C18 C -0.2775(17) 1.1014(17) -0.0435(16) 0.051(4) Uani 1 1 d . . . . .
H18 H -0.3640 1.1470 -0.0712 0.061 Uiso 1 1 calc R . . . .
C19 C -0.286(3) 1.0235(19) 0.356(3) 0.074(7) Uani 1 1 d . . . . .
H19 H -0.2055 1.0755 0.3787 0.088 Uiso 1 1 calc R . . . .
C20 C -0.2696(15) 1.0135(15) 0.0274(12) 0.038(3) Uani 1 1 d . . . . .
H20 H -0.3507 0.9996 0.0499 0.046 Uiso 1 1 calc R . . . .
C22 C -0.269(2) 0.918(2) 0.4020(17) 0.058(5) Uani 1 1 d . . . . .
H22 H -0.1782 0.8989 0.4587 0.070 Uiso 1 1 calc R . . . .
C25 C -0.2031(18) 0.5053(14) 0.2262(12) 0.038(3) Uani 1 1 d . . . . .
H25 H -0.2090 0.5190 0.1499 0.046 Uiso 1 1 calc R . . . .
C26 C -0.041(2) 0.4753(19) 0.2932(18) 0.061(5) Uani 1 1 d . . . . .
H26A H 0.0182 0.5446 0.3142 0.091 Uiso 1 1 calc GR . . . .
H26B H -0.0009 0.4281 0.2493 0.091 Uiso 1 1 calc GR . . . .
H26C H -0.0355 0.4341 0.3588 0.091 Uiso 1 1 calc GR . . . .
C33 C -0.521(2) 0.8682(19) 0.283(2) 0.068(6) Uani 1 1 d . . . . .
H33 H -0.6019 0.8165 0.2606 0.082 Uiso 1 1 calc R . . . .
C39 C -0.421(3) 1.0542(16) 0.274(2) 0.069(6) Uani 1 1 d . . . . .
H39 H -0.4348 1.1286 0.2456 0.083 Uiso 1 1 calc R . . . .
C42 C -0.2180(15) 0.7732(12) 0.1486(10) 0.027(2) Uani 1 1 d . . . . .
C49 C -0.307(3) 0.4053(18) 0.2211(15) 0.061(5) Uani 1 1 d . . . . .
H49A H -0.3035 0.3880 0.2946 0.092 Uiso 1 1 calc GR . . . .
H49B H -0.2748 0.3393 0.1910 0.092 Uiso 1 1 calc GR . . . .
H49C H -0.4090 0.4251 0.1745 0.092 Uiso 1 1 calc GR . . . .
C0AA C -0.537(3) 0.973(2) 0.234(2) 0.084(8) Uani 1 1 d . . . . .
H0AA H -0.6255 0.9910 0.1743 0.101 Uiso 1 1 calc R . . . .
C11 C -0.096(3) 0.6830(16) 0.7606(13) 0.053(4) Uani 1 1 d . . . . .
H11 H -0.0022 0.6536 0.8062 0.063 Uiso 1 1 calc R . . . .
C2AA C -0.5309(18) 0.6177(15) 0.3894(15) 0.045(4) Uani 1 1 d . . . . .
H2AA H -0.5090 0.5383 0.4091 0.068 Uiso 1 1 calc GR . . . .
H2AB H -0.5838 0.6241 0.3105 0.068 Uiso 1 1 calc GR . . . .
H2AC H -0.5931 0.6482 0.4272 0.068 Uiso 1 1 calc GR . . . .
C9 C -0.3684(19) 0.7802(16) 0.6260(14) 0.048(4) Uani 1 1 d . . . . .
H9 H -0.4596 0.8134 0.5809 0.057 Uiso 1 1 calc R . . . .
C1AA C -0.0246(17) 1.0586(15) -0.0350(11) 0.041(4) Uani 1 1 d . . . . .
H1AA H 0.0590 1.0754 -0.0538 0.049 Uiso 1 1 calc R . . . .
C1 C -0.318(2) 0.7949(16) 0.7378(14) 0.052(5) Uani 1 1 d . . . . .
H1 H -0.3747 0.8387 0.7689 0.062 Uiso 1 1 calc R . . . .
C2 C -0.185(2) 0.7455(17) 0.8051(12) 0.051(4) Uani 1 1 d . . . . .
H2 H -0.1536 0.7538 0.8818 0.061 Uiso 1 1 calc R . . . .
F1 F -0.1600(17) 1.2088(13) -0.1464(11) 0.082(4) Uani 1 1 d . . . . .
C3AA C -0.1509(19) 1.1222(16) -0.0744(13) 0.045(4) Uani 1 1 d . . . . .


_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
P2 C7 1.794(13) . ?
P2 C10 1.800(14) . ?
P2 C15 1.814(12) . ?
P2 C2AA 1.800(17) . ?
S3 C42 1.709(13) . ?
N4 C6 1.447(18) . ?
N4 C42 1.313(17) . ?
C6 C15 1.546(14) . ?
C6 C25 1.51(2) . ?
C7 C16 1.38(2) . ?
C7 C9 1.40(2) . ?
C10 C22 1.40(2) . ?
C10 C33 1.38(2) . ?
C12 C14 1.379(19) . ?
C12 C1AA 1.37(2) . ?
N13 C14 1.415(19) . ?
N13 C42 1.350(19) . ?
C14 C20 1.39(2) . ?
C16 C11 1.41(2) . ?
C18 C20 1.36(2) . ?
C18 C3AA 1.42(2) . ?
C19 C22 1.35(3) . ?
C19 C39 1.37(4) . ?
C25 C26 1.50(2) . ?
C25 C49 1.51(3) . ?
C33 C0AA 1.36(3) . ?
C39 C0AA 1.40(4) . ?
C11 C2 1.39(3) . ?
C9 C1 1.36(2) . ?
C1AA C3AA 1.34(3) . ?
C1 C2 1.37(3) . ?
F1 C3AA 1.353(19) . ?

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
C7 P2 C10 108.5(6) . . ?
C7 P2 C15 109.3(6) . . ?
C7 P2 C2AA 108.5(8) . . ?
C10 P2 C15 112.0(6) . . ?
C10 P2 C2AA 111.0(8) . . ?
C2AA P2 C15 107.5(7) . . ?
C42 N4 C6 127.1(11) . . ?
N4 C6 C15 107.9(10) . . ?
N4 C6 C25 111.3(11) . . ?
C25 C6 C15 111.6(11) . . ?
C16 C7 P2 121.3(10) . . ?
C16 C7 C9 119.8(13) . . ?
C9 C7 P2 118.8(12) . . ?
C22 C10 P2 118.7(12) . . ?
C33 C10 P2 122.3(12) . . ?
C33 C10 C22 119.0(16) . . ?
C1AA C12 C14 122.2(14) . . ?
C42 N13 C14 127.4(12) . . ?
C12 C14 N13 119.2(13) . . ?
C12 C14 C20 118.3(13) . . ?
C20 C14 N13 121.9(12) . . ?
C6 C15 P2 113.5(8) . . ?
C7 C16 C11 119.7(15) . . ?
C20 C18 C3AA 118.4(15) . . ?
C22 C19 C39 120(2) . . ?
C18 C20 C14 120.6(13) . . ?
C19 C22 C10 120.8(18) . . ?
C26 C25 C6 113.1(14) . . ?
C26 C25 C49 111.1(17) . . ?
C49 C25 C6 112.3(14) . . ?
C0AA C33 C10 120(2) . . ?
C19 C39 C0AA 119.7(18) . . ?
N4 C42 S3 123.5(11) . . ?
N4 C42 N13 114.2(12) . . ?
N13 C42 S3 122.2(10) . . ?
C33 C0AA C39 120(2) . . ?
C2 C11 C16 118.5(17) . . ?
C1 C9 C7 120.6(16) . . ?
C3AA C1AA C12 118.3(13) . . ?
C9 C1 C2 120.3(14) . . ?
C1 C2 C11 121.1(14) . . ?
C1AA C3AA C18 122.0(15) . . ?
C1AA C3AA F1 119.7(15) . . ?
F1 C3AA C18 118.3(16) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-06-21
_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 4.343
_oxdiff_exptl_absorpt_empirical_full_min 0.312
